US20060112850A1 - Micronized wood preservative formulations in organic carriers - Google Patents
Micronized wood preservative formulations in organic carriersDownload PDFInfo
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- US20060112850A1 US20060112850A1US11/243,640US24364005AUS2006112850A1US 20060112850 A1US20060112850 A1US 20060112850A1US 24364005 AUS24364005 AUS 24364005AUS 2006112850 A1US2006112850 A1US 2006112850A1
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/16—Heavy metals; Compounds thereof
- A01N59/20—Copper
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/005—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process employing compositions comprising microparticles
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/16—Inorganic impregnating agents
- B27K3/22—Compounds of zinc or copper
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/343—Heterocyclic compounds
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/52—Impregnating agents containing mixtures of inorganic and organic compounds
Definitions
- the present inventionpertains to wood preservation, and more specifically to the use of micronized metals, metal compounds, and organic biocides as wood preservatives.
- Wood preserving compositionsare used to protect wood and other cellulose-based materials, such as paper, particleboard, textiles, rope, etc., from attack by wood-destroying organisms, such as, for example, fungi, bacteria and insects.
- Conventional wood preserving compositionsoften contain inorganic compounds, organic biocides, or both in an organic carrier.
- inorganic compounds used heretoforeare compounds of copper, zinc, tin, boron, fluoride, etc.
- Organic biocides used heretoforeinclude insecticides, fungicides, moldicides, algaecides, bactericides, etc. that have been dissolved in an oil-borne carrier.
- Examples of such compoundsare azoles, carbamates, isothiazolinones, thiocyanates, sulfenamides, quaternary phosphonium compounds, quaternary ammonium compounds, nitrites, pyridines, etc.
- the preparation of such compounds in organic carriersis desirable because many organic carriers can impart water repellency and dimensional stability to cellulosic substrates such as wood.
- many inorganic compounds and organic biocideshave limited solubility in common and desirable organic carriers, and heretofore, special measures have been taken to overcome the solubility hurdle.
- inorganic compohave been added to organic carriers as organo-metallic compounds or have been complexed with an organic moiety to enhance its solubility characteristics in a desired organic carrier.
- Another technique which has been usedis the formation of a water-in-oil emulsion in which compounds are dissolved in water as organo-metallic compounds, and the aqueous product is mixed with emulsifying compounds to produce the emulsion.
- these methodsdo not work for many desirable combinations of inorganic/organic component and organic solvent. Such solutions have remained difficult to prepare.
- the present inventionprovides compositions and methods for preservation of wood.
- the compositioncomprises one or more micronized inorganic compounds, organic biocides, or both, and an organic carrier in which the micronized compounds are of low solubility.
- inorganic compoundsincludes metal compounds, as well as inorganic complexes comprising one or more metal ions which are complexed with organic moieties.
- a method for the preparation of the compositioncomprises the steps of providing an organic carrier and an inorganic compound, organic biocide, or both, which are insoluble in the organic carrier, and grinding them into micronized particles in the presence of dispersants and optionally, the carrier, such that a stable dispersion of micronized particles is formed. These compounds are ground by standard techniques known in the art.
- the inorganic compound/organic biocide particleshave a size in the range of 0.001 microns to 25.0 microns.
- compositions of the present inventioncan be impregnated into cellulosic materials such as wood by standard methods, such as vacuum/pressure methods.
- FIG. 1depicts coniferous wood anatomy.
- FIG. 2depicts the border pit structure for coniferous woods.
- micronized preservative compositionDisclosed herein is a micronized preservative composition, a method for its preparation, and method for its use thereof in the treatment of cellulosic material, especially wood.
- the leaching of metal element from the treated woodcan be less than that observed with non-micronized compositions currently used in the art.
- Metals or metal compounds which can be used in the micronized preservative compositions of the present invention in their elemental form or as compoundsinclude transition elements (including the lanthanide and actinide series elements) such as strontium, barium, arsenic, antimony, bismuth, lead, gallium, indium, thallium, tin, zinc, cadmium, silver, nickel, etc. Such compounds should exhibit a relatively low solubility in the organic liquid which is to be used as a carrier.
- a preferred metalis copper. Accordingly, in one embodiment, copper or copper compounds are used.
- the copper or copper compounds which can be usedinclude cuprous oxide (a source of copper (I) ions), cupric oxide (a source of copper (II) ions), copper hydroxide, copper carbonate, basic copper carbonate, copper oxychloride, copper 8-hydroxyquinolate, copper dimethyldithiocarbamate, copper omadine, copper borate, and copper residues (e.g., copper metal byproducts).
- Organic biocidessuch as fungicides, insecticides, moldicides, bactericides, algaecides etc. from chemical classes including azoles, carbamates, isothiazolinones, thiocyanates, sulfenamides, quaternary phosphonium compounds, quaternary ammonium compounds, nitriles, pyridines, etc. and mixtures thereof can be used with the present invention and are well known to those skilled in the art.
- the organic biocides used in the present inventionmay have varying degrees of solubility, depending upon the organic biocide and carrier which is used.
- the organic biocidemay be either micronized or soluble in the carrier used, with the provision that if the composition does not contain a micronized metal/metal compound component, the organic biocide is present in the carrier as micronized particles.
- Some non-limiting examples of organic biocidesare listed below.
- aliphatic nitrogen fungicidessuch as, for example: butylamine; cymoxanil; dodicin; dodine; guazatine; iminoctadine amide fungicides, such as, for example: carpropamid; chloraniformethan; cyazofamid; cyflufenamid; diclocymet; ethaboxam; fenoxanil; flumetover; furametpyr; prochloraz; quinazamid; silthiofam; triforine; benalaxyl-M; furalaxyl; metalaxyl; metalaxyl-M; pefurazoate; benzohydroxamic acid; tioxymid; trichlamide; zarilamid; zoxamide; cyclafuramid; furmecyclox dichlofluanid; tolylfluanid benthiavalicarb; iprovalicarb; be
- micronizedmeans a particle size in the range of 0.001 to 25 microns.
- particle sizerefers to the largest axis of the particle, and in the case of a generally spherical particle, the largest axis is the diameter.
- the micronized particlescan be obtained by wetting/dispersing and grinding the inorganic compounds, with or without organic carriers, using a grinding mill.
- micronizeddoes not refer only to particles which have been produced by the finely dividing, such as by mechanical grinding, of materials which are in bulk or other form, but to particles in the foregoing size range, whether they are ground from larger stock, precipitated out of solution, formed using nanotechnological methods, formed in situ, etc.
- the particlesbe formed in the presence of dispersants, such as stabilizers, wetting agents, surfactants, etc., such that a stable particle dispersion is formed.
- dispersantssuch as stabilizers, wetting agents, surfactants, etc.
- Standard dispersantscan be used, such as acrylic copolymers, polymers with pigment affinic groups or other modifications which give them affinity for the micronized component(s) (“modified”).
- Other dispersantsare modified polyacrylate, acrylic polymer emulsions, modified lignin, organically modified polysiloxane, modified polyurethane, polycarboxylate ether, modified fatty acids and fatty acid esters, modified polyether, modified polyamides, and the like.
- a “dispersion” of micronized particlesshould be interpreted to encompass situations in which particles are present with sizes outside the micronized range. However, it is preferred that greater than 80 wt % of the particles have diameters in the micronized range, and even more preferred that greater than 60 wt % of the micronized particles have a size of between 0.05 to 1.0 microns.
- All embodimentscontain at least one metal/metal compound or organic biocide which is present as a micronized dispersion.
- the compositioncomprises both types of components, either can be present in micronized form.
- both the inorganic compound component and the organic biocide componentare present as micronized particles.
- an inorganic compound or an organic biocide componentwill generally be considered to have the ability to be present in a wood preservative solution as micronized particles (i.e., little or no dissolution in the carrier), if the compound has a solubility in the organic carrier of less than or equal to 0.5 g per 100 grams of carrier at 25° C. More preferred is a solubility of less than or equal to 0.1 g per 100 grams of carrier at 25° C.
- compositions of the present inventioncan be prepared and stored as a concentrate, if desired, which can be diluted with an appropriate reconstituent to give a solution having a desired concentration of micronized component for applying to wood.
- an appropriate reconstituentto give a solution having a desired concentration of micronized component for applying to wood.
- Included within the ambit of the present inventionare situations in which the organic carrier used to reconstitute a concentrate solution is different from the organic carrier which is present in the concentrate. Such a situation may arise, for example, if further dilution with the same organic carrier which is in the concentrate would cause appreciable dissolution of the micronized inorganic component.
- a second organic carriermay have properties which are more suited to the application for which the composition is to be used than the carrier which makes up the concentrate.
- compositions which contain extremely high weight percent of micronized particlesmay be of high viscosity, and such solutions may require measures such as high pressures to ensure penetration.
- viscosity of the compositionis dependent upon the chosen carrier as well as the identity of the micronized component, and it is within the abilities of one skilled in the art to dilute or otherwise reduce the concentration of micronized component if excessive viscosity prevents or inhibits penetration.
- solutions having a micronized particle wt % in excess of 50 wt %may require the use of high pressures to achieve significant penetration.
- a solution which is a concentrate which is intended for dilution before usemay have a wt % of micronized particles which is even higher than 50 wt %.
- the wood preservative solutioncan have a micronized particle wt % as high as 85 wt % or as low as 0.00001 wt %, although for some applications, concentrations outside this range may be appropriate.
- concentrations outside this rangeincludes both ready-to-apply solutions and concentrates.
- compositions of the present inventionit can be desirable to use components in addition to the inorganic compound, organic biocide and organic carrier components in order to enhance the performance of the wood preservative solution.
- Such componentsmay be used as dispersants, defoamers, weathering agents, colorants, etc.
- the preservative solutions of the present inventioncan be prepared in a variety of ways.
- the component or components which are to be present as micronized particles in the preservative solutioncan be added to the carrier as a dispersion of micronized particles in a liquid phase, or they can be added to the carrier as large particulate or other solid form before grinding the particles to micronized size, preferably in the presence of dispersants.
- Solid componentscan be added as large particulate for later grinding, or as micronized particulate. If desired, micronized solids can be added directly to a carrier which contains a dispersant.
- micronized particlescan be obtained by grinding a metal/metal compounds or organic biocide component in the presence of a wetting agent and/or a dispersant using a commercially available grinding mill in the absence or presence of a solution. It is convenient to grind the particles in the presence of a carrier and a dispersant such that the suspension is formed in the carrier without the additional step of adding the dispersion to the carrier.
- micronized compoundsmay also be purchased from commercial sources and, if needed, ground further, optionally in the absence of the carrier.
- micronized compounds and biocides in an organic carriercan form a finely dispersed suspension with or without addition of a thickener.
- the resulting dispersioncan optionally be mixed with a variety of biocides which are soluble in the carrier.
- the soluble componentscan be added to the organic carrier prior to, during or after the micronization of the components.
- micronized particlescan be first made (by any suitable means) and then dispersed in the carrier.
- Other compounds and biocides, such as organic or inorganic biocides, soluble or insoluble,can be added to the dispersion, if desired.
- This inventionalso allows the addition of performance enhancing non-biocidal products such as water repellants, colorants, emulsifying agents, dispersants, stabilizers, UV inhibitors, drying agents, polymer systems and the like disclosed herein to further enhance the performance of the system or the appearance and performance of the resulting treated products.
- non-biocidal productssuch as water repellants, colorants, emulsifying agents, dispersants, stabilizers, UV inhibitors, drying agents, polymer systems and the like disclosed herein to further enhance the performance of the system or the appearance and performance of the resulting treated products.
- the ambit of the present inventionincludes the use of a wide range of organic carriers.
- organic carriersthat can be used, either alone, or as mixtures, as solubility allows, include:
- Aminessuch as, for example: Diamylamine, Diethylamine, Diisopropylamine, Dimethylethylamine, Di-n-Butylamine, Mono-2-Ethylhexyamine, Monoamylamine, Monoethylamine 70%, Monoisopropylamine, Anhy., Mono-n-Butylamine, Triamylamine, Triethylamine, Tri-n-Butylamine, Dibutylaminoethanol, Diethylaminoethanol, Diethylaminoethoxyethanol, Diisopropylaminoethanol, Dimethylamino-2P, 77% Mixed, Dimethylamino-2-P, Anhy., Dimethylaminoethanol, Dimethylaminoethoxyethanol, Ethlylaminoethanol, Ethylaminoethanol, Mixed, Isopropylaminoethanol, Isopropylaminoethanol, Mixed, Methyldiethanolamine, Monomethylaminoethanol, Mono-n-
- Glycolssuch as, for example: Diethylene Glycol, Dipropylene Glycol, Ethylene Glycol, Glycerine 96%, 99%, U.S.P., Glycerine, Hexylene Glycol, Neol® Neopentyiglycol, Polyethylene Glycol, Polypropylene Glycol, Propylene Glycol Ind.,U.S.P., Tetraethylene Glycol, Triethylene Glycol, Tripropylene Glycol;
- Ketonessuch as, for example: Acetone, Cyclohexanone, Diacetone, DIBK-Diisobutyl Ketone, Isophorone, MAK-Methyl Amyl Ketone, MEK-Methyl Ethyl Ketone, MIAK-Methyl Isoamyl Ketone, MIBK-Methyl Isobutyl Ketone, MPK-Methyl Propyl Ketone;
- Esterssuch as, for example: Amyl Acetate, Dibasic Ester, Ethyl Acetate, 2 Ethyl Hexyl Acetate, Ethyl Propionate, Exxate® Acetate Esters, Isobutyl Acetate, Isobutyl Isobuterate, Isopropyl Acetate, n-Butyl Acetate, n-Butyl Propionate, n-Pentyl Propionate, n-Propyl Acetate;
- Alcoholssuch as, for example: Amyl Alcohol, Benzyl Alcohol, Cyclohexanol, Ethyl Alcohol-Denatured, 2-Ethyl Hexanol, Exxal 8® Isooctyl Alcohol, Exxal 10® Isodecyl Alcohol, Exxal 13® Tridecyl Alcohol, Furfuryl Alcohol, Isobutyl Alcohol, Isopropyl Alcohol 99% Anhy, Methanol, Methyl Amyl Alcohol (MIBC), n-Butyl Alcohol, n-Propyl Alcohol, Neodol® Linear Alcohol, Secondary Butyl Alcohol, Tertiary Butyl Alcohol, Tetrahydrofurfryl Alcohol, Texanol Ester Alcohol®, UCAR Filmer IBT®;
- MIBCMethyl Amyl Alcohol
- MIBCMethyl Amyl Alcohol
- n-Butyl Alcoholn-Propyl Alcohol
- Neodol® Linear AlcoholSecondary Butyl Alcohol, Ter
- Halogenated Carrierssuch as, for example: Methylene Chloride, Monochlorobenzene, Orthodichlorobenzene, Perchloroethylene, Trichloroethylene, Vertrel® Hydrofluorocarbon;
- Aliphatic Carrierssuch as, for example: Heptane, Hexane, Kerosene, Lacquer Diluent, Mineral Seal Oil, Mineral Spirits, n-Pentane, OMS-Odorless Mineral Spirits, Rubber Solvent, 140 Solvent, 360 Solvent, Textile Spirits®, VM&P;
- Aromatic Carrierssuch as, for example: Aromatic 100, Aromatic 150, Aromatic 200, Heavy Aromatic Solvent, Panasol®, Toluene, Xylene;
- Terpene Carrierssuch as, for example: Alpha-Pinene, Wood, Dipentene 122®, D-Limonene, Herco® Pine Oil, Solvenol®, Steam Distilled Turpentine, Terpineol®, Yarmor® 302, 302-W Pine Oil;
- Other carriersincluding, for example: mineral oil, linseed oil, olive oil, vegetable oil, methoxypropyl acetate, isopropyl alcohol, castor oil, Arconate HP® Propylene Carbonate, #2 fuel oil, Cypar® Cycloparaffin Solvent, DMF—dimethyl formamide, formamide, Exxprint® Ink Oil/Solvent, furfural, Isopar® Isoparaffin Solvent, MTBE—methyl tert-butyl ether, NMP—N-methyl pyrrolidone, Norpar® Normal Paraffin Solvent, Proglyde DMM® Glycol Diether, THF—tetrahydrofuran, Varsol® Aliphatic Solvent.
- mineral oillinseed oil
- olive oilvegetable oil
- methoxypropyl acetateisopropyl alcohol
- castor oilArconate HP® Propylene Carbonate
- Cypar® Cycloparaffin SolventDMF—dimethyl formamide, formamide, Exxprint
- FIG. 1depicts the anatomy of coniferous wood. As shown in FIG. 2 , the primary entry and movement of fluids through wood tissue occurs primarily through the tracheids and border pits. Tracheids have a diameter of about thirty microns. Fluids are transferred between wood cells by means of border pits.
- the overall diameter of the border pit chamberstypically varies from a several microns up to thirty microns while, the diameter of the pit openings (via the microfibrils) typically varies from several hundredths of a micron to several microns.
- FIG. 2depicts the border pit structure for coniferous woods.
- Particle sizes of the metal or low water solubility organic biocide used in the compositionwhich exceed 30 microns tend to be filtered by the surface of the wood, thus not attaining a desired penetration and fluid flow through the wood tissue.
- particle size of the micronized particles used in the dispersion formulation disclosed hereincan have a long axis dimension (“size”) between 0.001-25 microns. In another embodiment, the particle size is between 0.001-10 microns. In another embodiment, the particle size is between 0.01 to 10 microns. If superior uniformity of penetration is desired, particle size of the additive used in the dispersion formulation disclosed herein should be between 0.01-1 microns.
- the particulate additivecomprise particles which have diameters which are not less than 0.001 microns.
- particle size distributional parameterscan affect the uniformity of particle distribution in the wood, as well as the leaching properties of treated wood. It is thus preferable to use particle size distributions which contain relatively few particle sizes outside the range of 0.001 to 25 microns. It is preferred that no more than 20 weight percent of the particles have diameters which are greater than 25 microns. Because smaller particles have an increased chance of leaching from the wood, it is also preferred that no more than 20 wt % of the particles have diameters under 0.001 microns.
- greater than 80 wt % of the particleshave a diameter in the range of 0.001 to 25 microns. In more preferred embodiments, greater than 85, 90, 95 or 99 wt % particles are in the range of 0.001 to 25 microns.
- At least 50 wt % of the particlesshould have diameters which are less than 10 microns. More preferred are particle distributions which have at least 65 wt % of the particles with sizes of less than 10 microns. In additional embodiments, less than 20 wt % of the particles have diameters of less than 1 micron.
- Examples 1 through 5demonstrate the formulation of the concentrated dispersions of copper compounds, copper compounds and various organic biocides, or organic biocides in an organic carrier.
- Examples 6 through 13demonstrate the preparation and use of treating fluids containing micronized dispersions for the treatment of wood.
- This exampledemonstrates the preparation of a dispersion of a micronized metal compound according to the present invention.
- Five hundred (500.0) grams of copper hydroxidewere added to a container containing 1091.7 grams white mineral spirits and 125.0 grams of dispersants/wetting agents. The mixture was mechanically stirred for 5 minutes and then placed in a grinding mill. The sample was ground for about 30 minutes, and a stable dispersion containing about 30 wt % copper hydroxide was obtained with an average particle size of 0.195 micrometers.
- This exampledemonstrates the preparation of a dispersion of a micronized metal compound according to the present invention.
- One thousand (1000.0) grams of basic copper carbonatewas mixed with 2158.3 grams of #2 fuel oil and 175.0 grams of wetting agents/dispersants. The mixture was mechanically stirred for 10 minutes. The mixture was then placed in a grinding mill and ground for about 20 minutes. A stable dispersion was obtained with an average particle size of 0.199 micrometers.
- This exampledemonstrates the preparation of a dispersion containing a micronized metal compound and a micronized organic biocide according to the present invention.
- One thousand (1000.0) grams of basic copper hydroxide and 20 grams of tebuconazolewere mixed with 3780 grams of mineral spirits and 200 grams of wetting agents/dispersants. The mixture was mechanically stirred for about 10 minutes. The mixture was then placed in a grinding mill and ground for about 30 minutes. A stable dispersion containing 25 wt % basic copper carbonate and 0.5wt % tebuconazole was obtained with an average particle size of 0.200 micrometers.
- This exampledemonstrates the preparation of a dispersion of a micronized metal compound according to the present invention.
- Three hundred (300) grams of copper 8-hydroxyquinolate (Cu-8)were mixed with 855 grams n-butyl acetate and 90.0 grams of dispersants. The mixture was mechanically mixed for about 5 minutes and placed in a grinding mill. The mixture was ground for about 30 minutes and a stable dispersion containing 25 wt % Cu-8 was obtained with an average particle size of 0.282 micrometers.
- This exampledemonstrates the uniform penetration achievable with the preservative compositions of the present invention.
- the cupric hydroxide dispersion from Example 1(38.5 g) was mixed with 7.5 g of N,N-dimethyl-1-dodecylamine-N-oxide (AO) and 2954.0 g of mineral spirits to produce a preservative treating fluid containing 0.385 wt % cupric hydroxide and 0.25 wt % AO.
- the fluidwas then used to treat 2′′ ⁇ 4′′ ⁇ 10′′ samples of southern pine sapwood using an initial vacuum of 28′′ Hg for 15 minutes, followed by a pressure cycle of 135 psi for 25 minutes and a final vacuum of 27′′ Hg for 10 minutes.
- the resulting treated woodwas weighed and found to have doubled its weight. Treated sample was cut and the cross sections sprayed with a copper indicator to determine copper penetration following the procedure described in American Wood Preservers' Association Standard A3-00, and the blue color indicates the presence of copper.
- This exampledemonstrates the uniform penetration achievable with the preservative compositions of the present invention.
- Fifty (50.0) g basic copper carbonate dispersion from Example 3were mixed with 2942.5 g of mineral spirits and 7.5 g of didecyldimethylammonium chloride. The product was mixed until uniformly dispersed and the treating solution containing the following compositions: Components Percent Cupric Oxide 0.50 Didecyldimethylammonium Chloride 0.25
- a southern pine stake measuring 1.5′′ ⁇ 3.5′′ ⁇ 10′′was placed in a laboratory retort with a vacuum of 27′′ Hg for 15 minutes.
- the treating solutionwas then pumped into the retort and the retort pressurized to 130 psi for 30 minutes.
- the solutionwas drained from the retort and the test stake weighed. Based on the weight pickup, the test stake doubled its weight and showed uniform penetration of the cupric oxide throughout the wood cross section.
- a preservative treating formulationwas prepared by adding 0.15 kg of copper carbonate dispersion from Example 2 to 0.025 kg of N,N-dimethyl-1-hexadecylamine-N-oxide and 4.825 kg of #2 fuel oil. This fluid was allowed to mix until a homogenous fluid was prepared. This fluid was used to treat southern pine test stakes by the full-cell process. The resulting stakes showed a uniform distribution of copper throughout the wood cells and were found to be resistant to decay and insect attack.
- a preservative treating compositionwas prepared by adding 0.1 kg of dispersion from Example 3 to 4.9 kg of #2 fuel oil.
- the resulting fluidcontained 0.50 wt % copper hydoxide and 0.01 wt % tebuconazole.
- This fluidwas then used to treat full-size lumber using the full-cell process wherein the wood is initially placed under a vacuum of 30′′ Hg for 30 minutes, followed by the addition of the treating solution.
- the systemwas then pressurized for 30 minutes at 110 psi.
- a final vacuum of 28′′ Hg for 30 minutesis applied to the wood to remove residual liquid.
- the woodis found to contain a uniform distribution of copper throughout the cross sections and is resistant to fungal and insect attack.
- This exampledemonstrates the uniform penetration achievable with the preservative compositions of the present invention, as well as their ability to preserve wood.
- Fifty-four grams of dispersion from Example 3 and 7.5 g of N,N-dimethyl-1-hexadecylamine-N-oxide (AO) (an organic biocide)were mixed with 2938.5 grams of #2 fuel oil to obtain a preservative treating fluid containing 0.45% copper hydroxide, 0.009 wt % tebuconazole and 0.25 wt % AO.
- the resulting fluidis used to treat red pine lumber using a modified full-cell process.
- the resulting stakesare air-dried and found to a uniform distribution of copper throughout the cross sections and are resistant to fungal and insect attack.
- This exampledemonstrates the uniform penetration achievable with the preservative compositions of the present invention, as well as their ability to preserve wood.
- This examplealso demonstrates the reconstitution of a concentrate containing an organic carrier which is different than the organic carrier which is used to reconstitute.
- a preservative treating fluidwas prepared by adding 16.0 g of Cu 8-hydroxyquinolate (Cu-8) dispersion from Example 4 to 3984.0 g of #2 fuel oil. The resulting fluid contained 0.1 wt % Cu-8. The fluid was used to treat southern pine lumber using a full cell process. The treated stakes are oven dried and found to contain a uniform distribution of particles throughout the cross sections and are resistant to fungal and insect attack.
- a preservative treating fluidwas prepared by mixing 175 g concentrated dispersion containing 20 wt % copper carbonate and 0.5 wt % cyproconazole with 3325.0 g methoxypropyl acetate. The resulting solution contains 1.0% copper carbonate and 0.025% cyproconazole and is used to treat southern pine lumber using a full cell process. The treated stakes are oven dried and found to contain a uniform distribution of copper and cyproconazole throughout the cross sections and are resistant to fungal and insect attack.
- a preservative treating fluidwas prepared by mixing 1.70 g concentrate from Example 5 with 998.3 g of #2 fuel oil.
- the resulting solutioncontains 0.05 wt % tebuconazole and 0.008 wt % bifenthrin is used to treat southern pine lumber using a full cell process.
- the treated stakesare oven drived and the exposed to fungal species and Formosan subterranean termite. The testing results indicate that the treated wood is resistant to fungal and insect attack.
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Abstract
Description
- This application claims priority to U.S. provisional application No. 60/618,729, filed on Oct. 14, 2004, the disclosure of which is hereby incorporated by reference.
- The present invention pertains to wood preservation, and more specifically to the use of micronized metals, metal compounds, and organic biocides as wood preservatives.
- Wood preserving compositions are used to protect wood and other cellulose-based materials, such as paper, particleboard, textiles, rope, etc., from attack by wood-destroying organisms, such as, for example, fungi, bacteria and insects. Conventional wood preserving compositions often contain inorganic compounds, organic biocides, or both in an organic carrier. Examples of inorganic compounds used heretofore are compounds of copper, zinc, tin, boron, fluoride, etc. Organic biocides used heretofore include insecticides, fungicides, moldicides, algaecides, bactericides, etc. that have been dissolved in an oil-borne carrier. Examples of such compounds are azoles, carbamates, isothiazolinones, thiocyanates, sulfenamides, quaternary phosphonium compounds, quaternary ammonium compounds, nitrites, pyridines, etc. The preparation of such compounds in organic carriers is desirable because many organic carriers can impart water repellency and dimensional stability to cellulosic substrates such as wood. However, many inorganic compounds and organic biocides have limited solubility in common and desirable organic carriers, and heretofore, special measures have been taken to overcome the solubility hurdle. For example, inorganic compo have been added to organic carriers as organo-metallic compounds or have been complexed with an organic moiety to enhance its solubility characteristics in a desired organic carrier. Another technique which has been used is the formation of a water-in-oil emulsion in which compounds are dissolved in water as organo-metallic compounds, and the aqueous product is mixed with emulsifying compounds to produce the emulsion. However, these methods do not work for many desirable combinations of inorganic/organic component and organic solvent. Such solutions have remained difficult to prepare.
- The present invention provides compositions and methods for preservation of wood. The composition comprises one or more micronized inorganic compounds, organic biocides, or both, and an organic carrier in which the micronized compounds are of low solubility. As used herein, the term inorganic compounds includes metal compounds, as well as inorganic complexes comprising one or more metal ions which are complexed with organic moieties.
- A method is provided for the preparation of the composition. The method comprises the steps of providing an organic carrier and an inorganic compound, organic biocide, or both, which are insoluble in the organic carrier, and grinding them into micronized particles in the presence of dispersants and optionally, the carrier, such that a stable dispersion of micronized particles is formed. These compounds are ground by standard techniques known in the art. The inorganic compound/organic biocide particles have a size in the range of 0.001 microns to 25.0 microns.
- The compositions of the present invention can be impregnated into cellulosic materials such as wood by standard methods, such as vacuum/pressure methods.
- When such a composition is used for preservation of wood, there is often only minimal leaching if any, of the micronized component(s) upon exposure of the wood to the elements during use, particularly if the micronized component(s) have limited or no solubility in water.
FIG. 1 depicts coniferous wood anatomy.FIG. 2 depicts the border pit structure for coniferous woods.- Disclosed herein is a micronized preservative composition, a method for its preparation, and method for its use thereof in the treatment of cellulosic material, especially wood. The leaching of metal element from the treated wood can be less than that observed with non-micronized compositions currently used in the art.
- Metals or metal compounds which can be used in the micronized preservative compositions of the present invention in their elemental form or as compounds include transition elements (including the lanthanide and actinide series elements) such as strontium, barium, arsenic, antimony, bismuth, lead, gallium, indium, thallium, tin, zinc, cadmium, silver, nickel, etc. Such compounds should exhibit a relatively low solubility in the organic liquid which is to be used as a carrier.
- A preferred metal is copper. Accordingly, in one embodiment, copper or copper compounds are used. The copper or copper compounds which can be used include cuprous oxide (a source of copper (I) ions), cupric oxide (a source of copper (II) ions), copper hydroxide, copper carbonate, basic copper carbonate, copper oxychloride, copper 8-hydroxyquinolate, copper dimethyldithiocarbamate, copper omadine, copper borate, and copper residues (e.g., copper metal byproducts).
- Organic biocides such as fungicides, insecticides, moldicides, bactericides, algaecides etc. from chemical classes including azoles, carbamates, isothiazolinones, thiocyanates, sulfenamides, quaternary phosphonium compounds, quaternary ammonium compounds, nitriles, pyridines, etc. and mixtures thereof can be used with the present invention and are well known to those skilled in the art. The organic biocides used in the present invention may have varying degrees of solubility, depending upon the organic biocide and carrier which is used. The organic biocide may be either micronized or soluble in the carrier used, with the provision that if the composition does not contain a micronized metal/metal compound component, the organic biocide is present in the carrier as micronized particles. Some non-limiting examples of organic biocides are listed below.
TABLE I aliphatic nitrogen fungicides, such as, for example: butylamine; cymoxanil; dodicin; dodine; guazatine; iminoctadine amide fungicides, such as, for example: carpropamid; chloraniformethan; cyazofamid; cyflufenamid; diclocymet; ethaboxam; fenoxanil; flumetover; furametpyr; prochloraz; quinazamid; silthiofam; triforine; benalaxyl-M; furalaxyl; metalaxyl; metalaxyl-M; pefurazoate; benzohydroxamic acid; tioxymid; trichlamide; zarilamid; zoxamide; cyclafuramid; furmecyclox dichlofluanid; tolylfluanid benthiavalicarb; iprovalicarb; benalaxyl; benalaxyl-M; boscalid; carboxin; fenhexamid; metalaxyl; metalaxyl-M; metsulfovax; ofurace; oxadixyl; oxycarboxin; pyracarbolid; thifluzamide; tiadinil; benodanil; flutolanil; mebenil; mepronil; salicylanilide; tecloftalam fenfuram; furalaxyl; furcarbanil; methfuroxam flusulfamide antibiotic fungicides, such as, for example: aureofungin; blasticidin-S; cycloheximide; griseofulvin; kasugamycin; natamycin; polyoxins; polyoxorim; streptomycin; validamycin; azoxystrobin; dimoxystrobin; fluoxastrobin; kresoxim-methyl; metominostrobin; orysastrobin; picoxystrobin; pyraclostrobin; trifloxystrobin aromatic fungicides, such as, for example: biphenyl chlorodinitronaphthalene; chloroneb; chlorothalonil; cresol; dicloran; hexachlorobenzene; pentachlorophenol; quintozene; sodium pentachlorophenoxide; tecnazene benzimidazole fungicide, such as, for example: benomyl; carbendazim; chlorfenazole; cypendazole; debacarb; fuberidazole; mecarbinzid rabenzazole; thiabendazole benzimidazole precursor fungicides, such as, for example: furophanate; thiophanate; thiophanate-methyl benzothiazole fungicides, such as, for example: bentaluron; chlobenthiazone; TCMTB bridged diphenyl fungicides, such as, for example: bithionol; dichlorophen; diphenylamine carbamate fungicides, such as, for example: benthiavalicarb; furophanat; eiprovalicarb; propamocarb; thiophanate; thiophanate-methyl; benomyl; carbendazim; cypendazole; debacarb; mecarbinzid; diethofencarb conazole fungicides, such as, for example: climbazole; clotrimazole; imazalil; oxpoconazole; prochloraz; azaconazole; triflumizole bromuconazole; cyproconazole; diclobutrazol; difenoconazole; diniconazole; diniconazole-M; epoxiconazole; etaconazole; fenbuconazole; fluquinconazole; flusilazole flutriafol; furconazole; furconazole-cis; hexaconazole; imibenconazole; ipconazole; metconazole; myclobutanil; penconazole; propiconazole; prothioconazole; quinconazole; simeconazole; tebuconazole; tetraconazole; triadimefon; triadimenol; triticonazole; uniconazole; uniconazole-P dicarboximide fungicides, such as, for example: famoxadone; fluoroimide; chlozolinate; dichlozoline; iprodione; isovaledione; myclozolin; procymidone; vinclozolin; captafol; captan; ditalimfos; folpet; thiochlorfenphim dinitrophenol fungicides, such as, for example: binapacryl; dinobuton; dinocap; dinocap-4; dinocap-6; dinocton; dinopenton; dinosulfon; dinoterbon; DNOC dithiocarbamate fungicides, such as, for example: azithiram; carbamorph; cufraneb; cuprobam; disulfiram; ferbam; metam; nabam; tecoram thiram; ziram; dazomet; etem; milneb; mancopper; mancozeb; maneb; metiram polycarbamate; propineb; zineb imidazole fungicides, such as, for example: cyazofamid; fenamidone; fenapani; l glyodin; iprodione; isovaledione; pefurazoate; triazoxide morpholine fungicides, such as, for example: aldimorp; h benzamorf; carbamorph; dimethomorph; dodemorph; fenpropimorph; flumorph; tridemorph organophosphorus fungicides, such as, for example: ampropylfos; ditalimfos; edifenphos; fosetyl; hexylthiofos; iprobenfos; phosdiphen; pyrazophos; tolclofos-methyl triamiphos oxathiin fungicides, such as, for example: carboxin; oxycarboxin oxazole fungicides, such as, for example: chlozolinate; dichlozoline; drazoxolon; famoxadone; hymexazol; metazoxolon; myclozolin; oxadixyl; vinclozolin pyridine fungicides, such as, for example: boscalid; buthiobate; dipyrithione; fluazinam; pyridinitril; pyrifenox; pyroxychlor; pyroxyfur pyrimidine fungicides, such as, for example: bupirimate; cyprodinil; diflumetorim; dimethirimol; ethirimol; fenarimol; ferimzone; mepanipyrim; nuarimol; pyrimethanil; triarimol pyrrole fungicides, such as, for example: fenpiclonil; fludioxonil; fluoroimide quinoline fungicides, such as, for example: ethoxyquin; halacrinate; 8-hydroxyquinoline sulfate; quinacetol; quinoxyfen; quinone fungicides, such as, for example: benquinox; chloranil; dichlone; dithianon quinoxaline fungicides, such as, for example: chinomethionat; chlorquinox; thioquinox thiazole fungicides, such as, for example: ethaboxam; etridiazole; metsulfovax; octhilinone; thiabendazole; thiadifluor; thifluzamide thiocarbamate fungicides, such as, for example: methasulfocarb; prothiocarb thiophene fungicides, such as, for example: ethaboxam; silthiofam triazine fungicides, such as, for example: anilazine triazole fungicides, such as, for example: bitertanol; fluotrimazole; triazbutil urea fungicides, such as, for example: bentaluron; pencycuron; quinazamid Other fungicides, such as, for example: acibenzolar; acypetacs; allyl alcohol; benzalkonium chloride; benzamacril; bethoxazin; carvone; chloropicrin; DBCP; dehydroacetic acid; diclomezine; diethyl pyrocarbonate; fenaminosulf; fenitropan; fenpropidin; formaldehyde; furfural; hexachlorobutadiene; iodomethane; isoprothiolane; methyl bromide; methyl isothiocyanate; metrafenone; nitrostyrene; nitrothal-isopropyl OCH; 2 phenylphenol; phthalide; piperalin; probenazole; proquinazid; pyroquilon; sodium orthophenylphenoxide; spiroxamine; sultropen; thicyofen; tricyclazole; methyl isothiocyanate antibiotic insecticides, such as, for example: allosamidin; thuringiensin; spinosad; abamectin; doramectin; emamectin; eprinomectin ivermectin; selamectin; milbemectin; milbemycin oxime; moxidectin botanical insecticides, such as, for example: anabasine; azadirachtin; d-limonene; nicotine; pyrethrins; cinerins; cinerin I; cinerin II; jasmolin; jasmolin II; pyrethrin I; pyrethrin II; quassia; rotenone; ryania; sabadilla carbamate insecticides, such as, for example: bendiocarb; carbaryl; benfuracarb; carbofuran; carbosulfan; decarbofuran; furathiocarb dimetan; dimetilan; hyquincarb; pirimicarb; alanycarb; aldicarb; aldoxycarb; butocarboxim; butoxycarboxim; methomyl; nitrilacarb; oxamyl; tazimcarb; thiocarboxime thiodicarb; thiofanox; allyxycarb; aminocarb; bufencarb; butacarb; carbanolate; cloethocarb; dicresyl; dioxacarb; EMPC; ethiofencarb; fenethacarb; fenobucarb; isoprocarb; methiocarb; metolcarb; mexacarbate; promacyl; promecarb; propoxur; trimethacarb; XMC; xylylcarb dinitrophenol insecticides; such as, for example: dinex; dinoprop; dinosam; DNOC; cryolite; sodium hexafluorosilicate; sulfluramid formamidine insecticides, such as, for example: amitraz; chlordimeform; formetanate; formparanate fumigant insecticides, such as, for example: acrylonitrile; carbon disulfide; carbon tetrachloride; chloroform; chloropicrin; para- dichlorobenzene; 1,2-dichloropropane; ethyl formate; ethylene dibromide; ethylene dichloride; ethylene oxide; hydrogen cyanide; iodomethane; methyl bromide; methylchloroform; methylene chloride; naphthalene; phosphine; sulfuryl fluoride; tetrachloroethane insect growth regulators, such as, for example: bistrifluron; buprofezin; chlorfluazuron; cyromazine; diflubenzuron; flucycloxuron; flufenoxuron; hexaflumuron; lufenuron; novaluron; noviflumuron; penfluron; teflubenzuron; triflumuron; epofenonane; fenoxycarb; hydroprene; kinoprene; methoprene; pyriproxyfen; triprene; juvenile hormone I; juvenile hormone II; juvenile hormone III; chromafenozide; halofenozide; methoxyfenozide; tebufenozide; α-ecdysone; ecdysterone; diofenolan; precocene I; precocene II; precocene III; dicyclanil nereistoxin analogue insecticides, such as, for example: bensultap; cartap; thiocyclam; thiosultap; flonicamid; clothianidin; dinotefuran; imidacloprid; thiamethoxam; nitenpyram; nithiazine; acetamiprid; imidacloprid; nitenpyram; thiacloprid organochlorine insecticides, such as, for example: bromo-DDT; camphechlor; DDT; pp'-DDT; ethyl-DDD; HCH; gamma-HCH; lindane; methoxychlor; pentachlorophenol; TDE; aldrin; bromocyclen; chlorbicyclen; chlordane; chlordecone; dieldrin; dilor; endosulfan; endrin; HEOD; heptachlor; HHDN; isobenzan; isodrin; kelevan; mirex organophosphorus insecticides bromfenvinfos; chlorfenvinphos; crotoxyphos; dichlorvos; dicrotophos; dimethylvinphos; fospirate; heptenophos; methocrotophos; mevinphos; monocrotophos; naled; naftalofos; phosphamidon; propaphos; schradan; TEPP; tetrachlorvinphos; dioxabenzofos; fosmethilan; phenthoate; acethion; amiton; cadusafos; chlorethoxyfos; chlormephos; demephion; demephion-O; demephion-S; demeton; demeton-O; demeton-S; demeton- methyl; demeton-O-methyl; demeton-S-methyl; demeton-S-methylsulphon; disulfoton; ethion; ethoprophos; IPSP; isothioate; malathion; methacrifos; oxydemeton-methyl; oxydeprofos; oxydisulfoton; phorate; sulfotep; terbufos; thiometon; amidithion; cyanthoate; dimethoate; ethoate-methyl; formothion; mecarbam; omethoate; prothoate; sophamide; vamidothion; chlorphoxim; phoxim; phoxim-methyl; azamethiphos; coumaphos; coumithoate; dioxathion; endothion; menazon; morphothion; phosalone; pyraclofos; pyridaphenthion; quinothion; dithicrofos; thicrofos; azinphos-ethyl; azinphos- methyl; dialifos; phosmet; isoxathion; zolaprofos; chlorprazophos; pyrazophos; chlorpyrifos; chlorpyrifos-methyl; butathiofos; diazinon; etrimfos; lirimfos; pirimiphos- ethyl; pirimiphos-methyl; primidophos; pyrimitate; tebupirimfos; quinalphos; quinalphos- methyl; athidathion; lythidathion; methidathion; prothidathion; isazofos; triazophos; azothoate; bromophos; bromophos-ethyl; carbophenothion; chlorthiophos; cyanophos; cythioate; dicapthon; dichlofenthion; etaphos; famphur; fenchlorphos; fenitrothion; fensulfothion; fenthion; fenthion-ethyl; heterophos; jodfenphos; mesulfenfos; parathion; parathion-methyl; phenkapton; phosnichlor; profenofos; prothiofos; sulprofos; temephos; trichlormetaphos-3; trifenofos; butonate; trichlorfon; mecarphon; fonofos; trichloronat; cyanofenphos; EPN; leptophos; crufomate; fenamiphos; fosthietan; mephosfolan; phosfolan; pirimetaphos; acephate; isocarbophos; isofenphos; methamidophos; propetamphos; dimefox; mazidox; dimefox; mazidox; mipafox oxadiazine insecticides, such as, for example: indoxacarb phthalimide insecticides, such as, for example: dialifos; phosmet; tetramethrin pyrazole insecticides, such as, for example: acetoprole; ethiprole; fipronil; tebufenpyrad; tolfenpyrad; vaniliprole pyrethroid insecticides, such as, for example: acrinathrin; allethrin; bioallethrin; barthrin; bifenthrin; bioethanomethrin; cyclethrin; cycloprothrin; cyfluthrin; beta-cyfluthrin; cyhalothrin; gamma-cyhalothrin; lambda- cyhalothrin; cypermethrin; alpha-cypermethrin; beta-cypermethrin; theta-cypermethrin; zeta-cypermethrin; cyphenothrin; deltamethrin; dimefluthrin; dimethrin; empenthrin; fenfluthrin; fenpirithrin; fenpropathrin; fenvalerate; esfenvalerate; flucythrinate; fluvalinate; tau-fluvalinate; furethrin; imiprothrin; permethrin; metofluthrin; biopermethrin; transpermethrin; phenothrin; prallethrin; profluthrin; pyresmethrin; resmethrin; bioresmethrin; cismethrin; tefluthrin; terallethrin; tetramethrin; tralomethrin; transfluthrin; etofenprox; flufenprox; halfenprox; protrifenbute; silafluofen pyrimidinamine insecticides, such as, for example: flufenerim; pyrimidifen pyrrole insecticides, such as, for example: chlorfenapyr tetronic acid insecticide, such as, for example: spiromesifen thiourea insecticides, such as, for example: diafenthiuron urea insecticide, such as, for example: flucofuron; sulcofuron Other insecticides, such as, for example: closantel; crotamiton; EXD; fenazaflor; fenoxacrim; hydramethylnon; isoprothiolane; malonoben; metoxadiazone; nifluridide; pyridaben; pyridalyl; rafoxanide; triarathene; triazamate Bactericides, such as, for example: bronopol, cresol, dichlorophen, dipyrithione; dodicin; fenaminosulf; formaldehyde; hydrargaphen; 8-hydroxyquinoline sulfate; kasugamycin; nitrapyrin; octhilinone; oxolinic acid; oxytetracycline; probenazole; streptomycin; tecloftalam; thiomersal - The ambit of the present invention includes the use of the above compounds and biocides in micronized form. The term “micronized” as used herein means a particle size in the range of 0.001 to 25 microns. The term “particle size” refers to the largest axis of the particle, and in the case of a generally spherical particle, the largest axis is the diameter. The micronized particles can be obtained by wetting/dispersing and grinding the inorganic compounds, with or without organic carriers, using a grinding mill. However, it should be understood that “micronized” does not refer only to particles which have been produced by the finely dividing, such as by mechanical grinding, of materials which are in bulk or other form, but to particles in the foregoing size range, whether they are ground from larger stock, precipitated out of solution, formed using nanotechnological methods, formed in situ, etc.
- It is preferred that the particles be formed in the presence of dispersants, such as stabilizers, wetting agents, surfactants, etc., such that a stable particle dispersion is formed. Standard dispersants can be used, such as acrylic copolymers, polymers with pigment affinic groups or other modifications which give them affinity for the micronized component(s) (“modified”). Other dispersants are modified polyacrylate, acrylic polymer emulsions, modified lignin, organically modified polysiloxane, modified polyurethane, polycarboxylate ether, modified fatty acids and fatty acid esters, modified polyether, modified polyamides, and the like.
- A “dispersion” of micronized particles should be interpreted to encompass situations in which particles are present with sizes outside the micronized range. However, it is preferred that greater than 80 wt % of the particles have diameters in the micronized range, and even more preferred that greater than 60 wt % of the micronized particles have a size of between 0.05 to 1.0 microns.
- All embodiments contain at least one metal/metal compound or organic biocide which is present as a micronized dispersion. When the composition comprises both types of components, either can be present in micronized form. In one embodiment, both the inorganic compound component and the organic biocide component are present as micronized particles.
- For the purposes herein, an inorganic compound or an organic biocide component will generally be considered to have the ability to be present in a wood preservative solution as micronized particles (i.e., little or no dissolution in the carrier), if the compound has a solubility in the organic carrier of less than or equal to 0.5 g per 100 grams of carrier at 25° C. More preferred is a solubility of less than or equal to 0.1 g per 100 grams of carrier at 25° C.
- The compositions of the present invention can be prepared and stored as a concentrate, if desired, which can be diluted with an appropriate reconstituent to give a solution having a desired concentration of micronized component for applying to wood. Included within the ambit of the present invention are situations in which the organic carrier used to reconstitute a concentrate solution is different from the organic carrier which is present in the concentrate. Such a situation may arise, for example, if further dilution with the same organic carrier which is in the concentrate would cause appreciable dissolution of the micronized inorganic component. A second organic carrier may have properties which are more suited to the application for which the composition is to be used than the carrier which makes up the concentrate.
- Compositions which contain extremely high weight percent of micronized particles may be of high viscosity, and such solutions may require measures such as high pressures to ensure penetration. However, viscosity of the composition is dependent upon the chosen carrier as well as the identity of the micronized component, and it is within the abilities of one skilled in the art to dilute or otherwise reduce the concentration of micronized component if excessive viscosity prevents or inhibits penetration. As a rule, solutions having a micronized particle wt % in excess of 50 wt % may require the use of high pressures to achieve significant penetration. However, a solution which is a concentrate which is intended for dilution before use may have a wt % of micronized particles which is even higher than 50 wt %.
- In general, the wood preservative solution can have a micronized particle wt % as high as 85 wt % or as low as 0.00001 wt %, although for some applications, concentrations outside this range may be appropriate. The foregoing range includes both ready-to-apply solutions and concentrates.
- In the compositions of the present invention it can be desirable to use components in addition to the inorganic compound, organic biocide and organic carrier components in order to enhance the performance of the wood preservative solution. Such components may be used as dispersants, defoamers, weathering agents, colorants, etc.
- The preservative solutions of the present invention can be prepared in a variety of ways. The component or components which are to be present as micronized particles in the preservative solution (the “solid component”) can be added to the carrier as a dispersion of micronized particles in a liquid phase, or they can be added to the carrier as large particulate or other solid form before grinding the particles to micronized size, preferably in the presence of dispersants. Solid components can be added as large particulate for later grinding, or as micronized particulate. If desired, micronized solids can be added directly to a carrier which contains a dispersant. The micronized particles can be obtained by grinding a metal/metal compounds or organic biocide component in the presence of a wetting agent and/or a dispersant using a commercially available grinding mill in the absence or presence of a solution. It is convenient to grind the particles in the presence of a carrier and a dispersant such that the suspension is formed in the carrier without the additional step of adding the dispersion to the carrier. Alternatively, micronized compounds may also be purchased from commercial sources and, if needed, ground further, optionally in the absence of the carrier.
- The micronized compounds and biocides in an organic carrier can form a finely dispersed suspension with or without addition of a thickener. The resulting dispersion can optionally be mixed with a variety of biocides which are soluble in the carrier.
- For preparing the compositions of the present invention, the soluble components can be added to the organic carrier prior to, during or after the micronization of the components. In one embodiment, micronized particles can be first made (by any suitable means) and then dispersed in the carrier. Other compounds and biocides, such as organic or inorganic biocides, soluble or insoluble, can be added to the dispersion, if desired.
- Heretofore, technology has typically required the addition of an organic co-solvent or chelating agent to solubilize or complex the copper or other inorganic or organic biocides into an organic carrier. Disadvantages of the typical approach used in the art include the limited number of inorganic and/or organic biocides that are suitable for use in the standard organic solvent systems currently accepted by the wood preserving industry. Some biocides would require solvents that have dangerously low flash points or have significant health or environmental hazards associated with their use. Furthermore, using current technologies, metal or biocide components may be prone to leaching. The use of the present invention allows the addition of a variety of inorganic and organic biocides to carrier systems which comply with the Standard P9 (Standards for Solvents and Formulations for Organic Preservative Systems) of the American Wood Preservers Association.
- This invention also allows the addition of performance enhancing non-biocidal products such as water repellants, colorants, emulsifying agents, dispersants, stabilizers, UV inhibitors, drying agents, polymer systems and the like disclosed herein to further enhance the performance of the system or the appearance and performance of the resulting treated products.
- The ambit of the present invention includes the use of a wide range of organic carriers. Non-limiting examples of organic carriers that can be used, either alone, or as mixtures, as solubility allows, include:
- Amines such as, for example: Diamylamine, Diethylamine, Diisopropylamine, Dimethylethylamine, Di-n-Butylamine, Mono-2-Ethylhexyamine, Monoamylamine, Monoethylamine 70%, Monoisopropylamine, Anhy., Mono-n-Butylamine, Triamylamine, Triethylamine, Tri-n-Butylamine, Dibutylaminoethanol, Diethylaminoethanol, Diethylaminoethoxyethanol, Diisopropylaminoethanol, Dimethylamino-2P, 77% Mixed, Dimethylamino-2-P, Anhy., Dimethylaminoethanol, Dimethylaminoethoxyethanol, Ethlylaminoethanol, Ethylaminoethanol, Mixed, Isopropylaminoethanol, Isopropylaminoethanol, Mixed, Methyldiethanolamine, Monomethylaminoethanol, Mono-n-Propylaminoethanol, n-Butylaminoethanol, n-Butyldiethanolamine, n-Butyldiethanolamine, Photo, t-Butylaminoethanol, t-butyldiethanolamine, Diethanolamine, Monoethanolamine, Triethanolamine, Triethanolamine 85%/99%, Diisopropanolamine, Monoisopropanolamine, Triisopropanolamine, Aminoethylethanolamine, Aminoethylpiperazine, Diethylenetriamine, Ethylenediamine, Piperazine 65%/Anhy., Piperazine, Tetraethylenepentamine, Triethylenetetramine, 3-Methoxypropylamine, AMP® Regular/95, Cyclohexylamine, Morpholine, Neutrol TE®;
- Glycols, such as, for example: Diethylene Glycol, Dipropylene Glycol, Ethylene Glycol, Glycerine 96%, 99%, U.S.P., Glycerine, Hexylene Glycol, Neol® Neopentyiglycol, Polyethylene Glycol, Polypropylene Glycol, Propylene Glycol Ind.,U.S.P., Tetraethylene Glycol, Triethylene Glycol, Tripropylene Glycol;
- Ketones such as, for example: Acetone, Cyclohexanone, Diacetone, DIBK-Diisobutyl Ketone, Isophorone, MAK-Methyl Amyl Ketone, MEK-Methyl Ethyl Ketone, MIAK-Methyl Isoamyl Ketone, MIBK-Methyl Isobutyl Ketone, MPK-Methyl Propyl Ketone;
- Esters such as, for example: Amyl Acetate, Dibasic Ester, Ethyl Acetate, 2 Ethyl Hexyl Acetate, Ethyl Propionate, Exxate® Acetate Esters, Isobutyl Acetate, Isobutyl Isobuterate, Isopropyl Acetate, n-Butyl Acetate, n-Butyl Propionate, n-Pentyl Propionate, n-Propyl Acetate;
- Alcohols such as, for example: Amyl Alcohol, Benzyl Alcohol, Cyclohexanol, Ethyl Alcohol-Denatured, 2-Ethyl Hexanol, Exxal 8® Isooctyl Alcohol, Exxal 10® Isodecyl Alcohol, Exxal 13® Tridecyl Alcohol, Furfuryl Alcohol, Isobutyl Alcohol, Isopropyl Alcohol 99% Anhy, Methanol, Methyl Amyl Alcohol (MIBC), n-Butyl Alcohol, n-Propyl Alcohol, Neodol® Linear Alcohol, Secondary Butyl Alcohol, Tertiary Butyl Alcohol, Tetrahydrofurfryl Alcohol, Texanol Ester Alcohol®, UCAR Filmer IBT®;
- Halogenated Carriers such as, for example: Methylene Chloride, Monochlorobenzene, Orthodichlorobenzene, Perchloroethylene, Trichloroethylene, Vertrel® Hydrofluorocarbon;
- Aliphatic Carriers such as, for example: Heptane, Hexane, Kerosene, Lacquer Diluent, Mineral Seal Oil, Mineral Spirits, n-Pentane, OMS-Odorless Mineral Spirits, Rubber Solvent, 140 Solvent, 360 Solvent, Textile Spirits®, VM&P;
- Aromatic Carriers such as, for example: Aromatic 100, Aromatic 150, Aromatic 200, Heavy Aromatic Solvent, Panasol®, Toluene, Xylene;
- Terpene Carriers such as, for example: Alpha-Pinene, Wood, Dipentene 122®, D-Limonene, Herco® Pine Oil, Solvenol®, Steam Distilled Turpentine, Terpineol®, Yarmor® 302, 302-W Pine Oil;
- Other carriers, including, for example: mineral oil, linseed oil, olive oil, vegetable oil, methoxypropyl acetate, isopropyl alcohol, castor oil, Arconate HP® Propylene Carbonate, #2 fuel oil, Cypar® Cycloparaffin Solvent, DMF—dimethyl formamide, formamide, Exxprint® Ink Oil/Solvent, furfural, Isopar® Isoparaffin Solvent, MTBE—methyl tert-butyl ether, NMP—N-methyl pyrrolidone, Norpar® Normal Paraffin Solvent, Proglyde DMM® Glycol Diether, THF—tetrahydrofuran, Varsol® Aliphatic Solvent.
- Also important is the penetration of the dispersed formulation into the cellular structure of the wood or other cellulose-based material. If the solids used in formulating the dispersion formulation disclosed herein have a particle size in excess of 30 microns, the particles may be filtered by the surface of the wood and thus may not be uniformly distributed within the cell and cell wall.
FIG. 1 depicts the anatomy of coniferous wood. As shown inFIG. 2 , the primary entry and movement of fluids through wood tissue occurs primarily through the tracheids and border pits. Tracheids have a diameter of about thirty microns. Fluids are transferred between wood cells by means of border pits. - The overall diameter of the border pit chambers typically varies from a several microns up to thirty microns while, the diameter of the pit openings (via the microfibrils) typically varies from several hundredths of a micron to several microns.
FIG. 2 depicts the border pit structure for coniferous woods. - Particle sizes of the metal or low water solubility organic biocide used in the composition which exceed 30 microns tend to be filtered by the surface of the wood, thus not attaining a desired penetration and fluid flow through the wood tissue.
- In one embodiment particle size of the micronized particles used in the dispersion formulation disclosed herein can have a long axis dimension (“size”) between 0.001-25 microns. In another embodiment, the particle size is between 0.001-10 microns. In another embodiment, the particle size is between 0.01 to 10 microns. If superior uniformity of penetration is desired, particle size of the additive used in the dispersion formulation disclosed herein should be between 0.01-1 microns.
- In addition to a recommended upper limit of 25 microns, Particles which are too small can leach out of the wood over time. It is thus generally recommended that the particulate additive comprise particles which have diameters which are not less than 0.001 microns.
- Particles which are too large can clog the wood, preventing it from taking in other particles and particles which are too small can leach from the wood. Thus particle size distributional parameters can affect the uniformity of particle distribution in the wood, as well as the leaching properties of treated wood. It is thus preferable to use particle size distributions which contain relatively few particle sizes outside the range of 0.001 to 25 microns. It is preferred that no more than 20 weight percent of the particles have diameters which are greater than 25 microns. Because smaller particles have an increased chance of leaching from the wood, it is also preferred that no more than 20 wt % of the particles have diameters under 0.001 microns. Regardless of the foregoing recommendations, it is generally preferred that greater than 80 wt % of the particles have a diameter in the range of 0.001 to 25 microns. In more preferred embodiments, greater than 85, 90, 95 or 99 wt % particles are in the range of 0.001 to 25 microns.
- For increased degree of penetration and uniformity of distribution, at least 50 wt % of the particles should have diameters which are less than 10 microns. More preferred are particle distributions which have at least 65 wt % of the particles with sizes of less than 10 microns. In additional embodiments, less than 20 wt % of the particles have diameters of less than 1 micron.
- The following examples are provided to further describe certain embodiment of the disclosure but are in no way limiting to the scope of disclosure. Examples 1 through 5 demonstrate the formulation of the concentrated dispersions of copper compounds, copper compounds and various organic biocides, or organic biocides in an organic carrier.
- Examples 6 through 13 demonstrate the preparation and use of treating fluids containing micronized dispersions for the treatment of wood.
- This example demonstrates the preparation of a dispersion of a micronized metal compound according to the present invention. Five hundred (500.0) grams of copper hydroxide were added to a container containing 1091.7 grams white mineral spirits and 125.0 grams of dispersants/wetting agents. The mixture was mechanically stirred for 5 minutes and then placed in a grinding mill. The sample was ground for about 30 minutes, and a stable dispersion containing about 30 wt % copper hydroxide was obtained with an average particle size of 0.195 micrometers.
- This example demonstrates the preparation of a dispersion of a micronized metal compound according to the present invention. One thousand (1000.0) grams of basic copper carbonate was mixed with 2158.3 grams of #2 fuel oil and 175.0 grams of wetting agents/dispersants. The mixture was mechanically stirred for 10 minutes. The mixture was then placed in a grinding mill and ground for about 20 minutes. A stable dispersion was obtained with an average particle size of 0.199 micrometers.
- This example demonstrates the preparation of a dispersion containing a micronized metal compound and a micronized organic biocide according to the present invention. One thousand (1000.0) grams of basic copper hydroxide and 20 grams of tebuconazole were mixed with 3780 grams of mineral spirits and 200 grams of wetting agents/dispersants. The mixture was mechanically stirred for about 10 minutes. The mixture was then placed in a grinding mill and ground for about 30 minutes. A stable dispersion containing 25 wt % basic copper carbonate and 0.5wt % tebuconazole was obtained with an average particle size of 0.200 micrometers.
- This example demonstrates the preparation of a dispersion of a micronized metal compound according to the present invention. Three hundred (300) grams of copper 8-hydroxyquinolate (Cu-8) were mixed with 855 grams n-butyl acetate and 90.0 grams of dispersants. The mixture was mechanically mixed for about 5 minutes and placed in a grinding mill. The mixture was ground for about 30 minutes and a stable dispersion containing 25 wt % Cu-8 was obtained with an average particle size of 0.282 micrometers.
- Five hundred (500.0) grams of tebuconazole and 80.0 grams of bifenthrin were mixed with 800.0 g of #2 fuel oil and 300.0 g of dispersants. The mixture was mechanically mixed for about 10 minutes and then transferred into a grinding mill. The mixture was ground for about 45 minutes and a stable dispersion was achieved with a concentration of tebuconazole of 29.8 wt % and bifenthrin of 4.8 wt %.
- This example demonstrates the uniform penetration achievable with the preservative compositions of the present invention. The cupric hydroxide dispersion from Example 1 (38.5 g) was mixed with 7.5 g of N,N-dimethyl-1-dodecylamine-N-oxide (AO) and 2954.0 g of mineral spirits to produce a preservative treating fluid containing 0.385 wt % cupric hydroxide and 0.25 wt % AO. The fluid was then used to treat 2″×4″×10″ samples of southern pine sapwood using an initial vacuum of 28″ Hg for 15 minutes, followed by a pressure cycle of 135 psi for 25 minutes and a final vacuum of 27″ Hg for 10 minutes. The resulting treated wood was weighed and found to have doubled its weight. Treated sample was cut and the cross sections sprayed with a copper indicator to determine copper penetration following the procedure described in American Wood Preservers' Association Standard A3-00, and the blue color indicates the presence of copper.
- This example demonstrates the uniform penetration achievable with the preservative compositions of the present invention. Fifty (50.0) g basic copper carbonate dispersion from Example 3 were mixed with 2942.5 g of mineral spirits and 7.5 g of didecyldimethylammonium chloride. The product was mixed until uniformly dispersed and the treating solution containing the following compositions:
Components Percent Cupric Oxide 0.50 Didecyldimethylammonium Chloride 0.25 - A southern pine stake measuring 1.5″×3.5″×10″ was placed in a laboratory retort with a vacuum of 27″ Hg for 15 minutes. The treating solution was then pumped into the retort and the retort pressurized to 130 psi for 30 minutes. The solution was drained from the retort and the test stake weighed. Based on the weight pickup, the test stake doubled its weight and showed uniform penetration of the cupric oxide throughout the wood cross section.
- This example demonstrates the uniform penetration achievable with the preservative compositions of the present invention, as well as their ability to preserve wood. A preservative treating formulation was prepared by adding 0.15 kg of copper carbonate dispersion from Example 2 to 0.025 kg of N,N-dimethyl-1-hexadecylamine-N-oxide and 4.825 kg of #2 fuel oil. This fluid was allowed to mix until a homogenous fluid was prepared. This fluid was used to treat southern pine test stakes by the full-cell process. The resulting stakes showed a uniform distribution of copper throughout the wood cells and were found to be resistant to decay and insect attack.
- This example demonstrates the uniform penetration achievable with the preservative compositions of the present invention, as well as their ability to preserve wood. A preservative treating composition was prepared by adding 0.1 kg of dispersion from Example 3 to 4.9 kg of #2 fuel oil. The resulting fluid contained 0.50 wt % copper hydoxide and 0.01 wt % tebuconazole. This fluid was then used to treat full-size lumber using the full-cell process wherein the wood is initially placed under a vacuum of 30″ Hg for 30 minutes, followed by the addition of the treating solution. The system was then pressurized for 30 minutes at 110 psi. A final vacuum of 28″ Hg for 30 minutes is applied to the wood to remove residual liquid. The wood is found to contain a uniform distribution of copper throughout the cross sections and is resistant to fungal and insect attack.
- This example demonstrates the uniform penetration achievable with the preservative compositions of the present invention, as well as their ability to preserve wood. Fifty-four grams of dispersion from Example 3 and 7.5 g of N,N-dimethyl-1-hexadecylamine-N-oxide (AO) (an organic biocide) were mixed with 2938.5 grams of #2 fuel oil to obtain a preservative treating fluid containing 0.45% copper hydroxide, 0.009 wt % tebuconazole and 0.25 wt % AO. The resulting fluid is used to treat red pine lumber using a modified full-cell process. The resulting stakes are air-dried and found to a uniform distribution of copper throughout the cross sections and are resistant to fungal and insect attack.
- This example demonstrates the uniform penetration achievable with the preservative compositions of the present invention, as well as their ability to preserve wood. This example also demonstrates the reconstitution of a concentrate containing an organic carrier which is different than the organic carrier which is used to reconstitute. A preservative treating fluid was prepared by adding 16.0 g of Cu 8-hydroxyquinolate (Cu-8) dispersion from Example 4 to 3984.0 g of #2 fuel oil. The resulting fluid contained 0.1 wt % Cu-8. The fluid was used to treat southern pine lumber using a full cell process. The treated stakes are oven dried and found to contain a uniform distribution of particles throughout the cross sections and are resistant to fungal and insect attack.
- This example demonstrates the uniform penetration achievable with the preservative compositions of the present invention, as well as their ability to preserve wood. A preservative treating fluid was prepared by mixing 175 g concentrated dispersion containing 20 wt % copper carbonate and 0.5 wt % cyproconazole with 3325.0 g methoxypropyl acetate. The resulting solution contains 1.0% copper carbonate and 0.025% cyproconazole and is used to treat southern pine lumber using a full cell process. The treated stakes are oven dried and found to contain a uniform distribution of copper and cyproconazole throughout the cross sections and are resistant to fungal and insect attack.
- A preservative treating fluid was prepared by mixing 1.70 g concentrate from Example 5 with 998.3 g of #2 fuel oil. The resulting solution contains 0.05 wt % tebuconazole and 0.008 wt % bifenthrin is used to treat southern pine lumber using a full cell process. The treated stakes are oven drived and the exposed to fungal species and Formosan subterranean termite. The testing results indicate that the treated wood is resistant to fungal and insect attack.
Claims (20)
1. A wood preservative composition comprising:
(a) an inorganic compound component selected from the group consisting of a metal, metal compound and combinations thereof; and/or an organic biocide component; and
(b) a liquid organic component;
wherein the inorganic compound component and/or organic biocide component in a) comprise a dispersion of particles in the liquid organic component, and wherein greater than 80 wt percent of the particles are micronized.
2. The composition ofclaim 1 , wherein the composition comprises an organic biocide component selected from the group consisting of biocides listed in Table 1.
3. The composition ofclaim 1 , wherein the composition comprises both an the inorganic compound component and an organic biocide component, and both of which are present as micronized particles.
4. The composition ofclaim 1 wherein the composition comprises an inorganic compound component which comprises copper, one or more copper compounds, or combinations thereof.
5. The composition ofclaim 4 , wherein the inorganic compound component is micronized and comprises one or more copper compounds that are selected from the group consisting of copper hydroxide, copper oxide copper carbonate, basic copper carbonate, copper oxychloride, copper 8-hydroxyquinolate, copper dimethyldithiocarbamate, copper omadine and copper borate.
6. The composition ofclaim 2 , wherein the organic biocide component comprises tebuconazole, propiconazole, cyproconazole, bifenthrin, permethrin, cypermethrin, 2-(thiocyanatomethylthio)benzothiazole, Chlorothalonil, Dichlofluanid, Kathon 930, Kathon WT, Methylisothiazolinone, Benzisothiazolin-3-one, 2-octyl-3-isothiazolone, Imidacloprid, Iodopropynyl Butylcarbamate, Fipronil, Carbendazim or Cyfluthrin.
7. The composition ofclaim 1 , wherein the liquid organic component comprises white mineral spirits, #2 fuel oil, n-butyl acetate or methoxypropyl acetate.
8. The composition ofclaim 5 , wherein the liquid organic component comprises white mineral spirits, #2 fuel oil, n-butyl acetate or methoxypropyl acetate.
9. The composition ofclaim 6 , wherein the liquid organic component comprises white mineral spirits, #2 fuel oil, n-butyl acetate or methoxypropyl acetate.
10. The composition ofclaim 1 wherein the micronized particles have a size of between 0.05 to 1.0 microns.
11. The composition ofclaim 1 , further comprising an agent selected from the group consisting of water repellants, colorants, emulsifying agents, dispersants, stabilizers and UV inhibitors.
12. A method for preserving a wood product comprising the step of contacting the product with a wood preservative composition ofclaim 1 .
13. The method ofclaim 12 , wherein the composition comprises 1) an inorganic compound component and 2) an organic biocide component selected from the group consisting of biocides listed in Table 1.
14. The method ofclaim 12 , further comprising the step of pressure treating the wood product with the wood preservative composition.
15. The method ofclaim 13 , wherein the inorganic compound component and the organic biocide component are present as micronized particles.
16. The method ofclaim 15 , wherein the inorganic component comprises one or more copper compounds that are selected from the group consisting of copper hydroxide, copper oxide copper carbonate, basic copper carbonate, copper oxychloride, copper 8-hydroxyquinolate, copper dimethyldithiocarbamate, copper omadine and copper borate; and wherein the organic biocide component comprises tebuconazole, propiconazole, cyproconazole, bifenthrin, permethrin, cypermethrin, 2-(thiocyanatomethylthio)benzothiazole, Chlorothalonil, Dichlofluanid, Kathon 930, Kathon WT, Methylisothiazolinone, Benzisothiazolin-3-one, 2-octyl-3-isothiazolone, Imidacloprid, Iodopropynyl Butylcarbamate, Fipronil, Carbendazim or Cyfluthrin.
17. The method ofclaim 12 , wherein the liquid organic component comprises white mineral spirits, #2 fuel oil, n-butyl acetate or methoxypropyl acetate.
18. The method ofclaim 16 , wherein the liquid organic component comprises white mineral spirits, #2 fuel oil, n-butyl acetate or methoxypropyl acetate.
19. The method ofclaim 16 , wherein the size of the copper compound particles is between 0.05 and 1.0 microns.
20. The methodclaim 12 , wherein the composition further comprises an agent selected from the group consisting of water repellants, colorants, emulsifying agents, dispersants, stabilizers and UV inhibitors.
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| US13/161,772US9775350B2 (en) | 2004-10-14 | 2011-06-16 | Micronized wood preservative formulations in organic carriers |
| US15/689,728US20170360042A1 (en) | 2004-10-14 | 2017-08-29 | Micronized wood preservative formulations in organic carriers |
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Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050255251A1 (en)* | 2004-05-17 | 2005-11-17 | Hodge Robert L | Composition, method of making, and treatment of wood with an injectable wood preservative slurry having biocidal particles |
| US20060075923A1 (en)* | 2004-10-12 | 2006-04-13 | Richardson H W | Method of manufacture and treatment of wood with injectable particulate iron oxide |
| US20070021385A1 (en)* | 2005-07-21 | 2007-01-25 | Jun Zhang | Compositions and methods for wood preservation |
| US20070131136A1 (en)* | 2004-04-27 | 2007-06-14 | Osmose, Inc. | Composition And Process For Coloring Wood |
| US20070259016A1 (en)* | 2006-05-05 | 2007-11-08 | Hodge Robert L | Method of treating crops with submicron chlorothalonil |
| US20080118575A1 (en)* | 2006-11-22 | 2008-05-22 | John William Ashmore | Antimicrobial composition useful for preserving wood |
| US20080175913A1 (en)* | 2007-01-09 | 2008-07-24 | Jun Zhang | Wood preservative compositions comprising isothiazolone-pyrethroids |
| US20080210121A1 (en)* | 2003-04-09 | 2008-09-04 | Jun Zhang | Micronized wood preservative formulations |
| US20080213608A1 (en)* | 2004-10-08 | 2008-09-04 | Richardson Hugh W | Milled Submicron Chlorothalonil With Narrow Particle Size Distribution, and Uses Thereof |
| US20090162410A1 (en)* | 2007-12-21 | 2009-06-25 | Jun Zhang | Process for preparing fine particle dispersion for wood preservation |
| US20090223408A1 (en)* | 2004-05-17 | 2009-09-10 | Phibrowood, Llc | Use of Sub-Micron Copper Salt Particles in Wood Preservation |
| US20090258943A1 (en)* | 2008-03-14 | 2009-10-15 | Keen Brian T | Hybrid strategies for reducing leaching of metal biocides from biodegradable substrates |
| US20100016426A1 (en)* | 2008-07-17 | 2010-01-21 | Hayson Kimberly S | Post-impregnation treatments to improve distribution of metal biocides in an impregnated substrate |
| US7666254B1 (en)* | 2006-08-18 | 2010-02-23 | Osmose, Inc. | Borate compositions for wood preservation |
| US20100119818A1 (en)* | 2004-05-13 | 2010-05-13 | Leach Robert M | Compositions and methods for treating cellulose-based materials with micronized additives |
| WO2010082840A1 (en)* | 2008-12-12 | 2010-07-22 | Tim Tech Chemicals Limited | Compositions for the treatment of timber and other wood substrates |
| US20100314117A1 (en)* | 2009-06-16 | 2010-12-16 | Jack Li | Asphaltene removal composition and methods |
| US20110091575A1 (en)* | 2007-12-13 | 2011-04-21 | Hayson Kimberly S | Strategies for reducing leaching of water-soluble metal biocides from treated wood products |
| GB2481526A (en)* | 2010-06-21 | 2011-12-28 | Arch Timber Protection Ltd | Wood preservative compositions useful for treating copper-tolerant fungi |
| US20120021222A1 (en)* | 2006-02-10 | 2012-01-26 | Kun Lian | Carbon-Encased Metal Nanoparticles and Sponges, Methods of Synthesis, and Methods of Use |
| US8158208B2 (en) | 2004-05-17 | 2012-04-17 | Osmose, Inc. | Method of preserving wood by injecting particulate wood preservative slurry |
| US8409627B2 (en) | 2003-06-17 | 2013-04-02 | Osmose, Inc. | Particulate wood preservative and method for producing the same |
| US8460759B2 (en) | 2003-04-09 | 2013-06-11 | Osmose, Inc. | Micronized wood preservative formulations |
| US8747908B2 (en) | 2003-04-09 | 2014-06-10 | Osmose, Inc. | Micronized wood preservative formulations |
| US9603358B2 (en) | 2011-11-04 | 2017-03-28 | Arch Timber Protection Limited | Additives for use in wood preservation |
| US9775350B2 (en) | 2004-10-14 | 2017-10-03 | Koppers Performance Chemicals Inc. | Micronized wood preservative formulations in organic carriers |
| US20190084182A1 (en)* | 2017-03-24 | 2019-03-21 | Koppers Performance Chemicals Inc. | Solvent-borne wood preservative compositions |
| US11312038B2 (en) | 2014-05-02 | 2022-04-26 | Arch Wood Protection, Inc. | Wood preservative composition |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2610046C (en)* | 2006-11-22 | 2011-04-26 | Rohm And Haas Company | Antimicrobial composition useful for preserving wood |
| US10632645B2 (en) | 2012-03-29 | 2020-04-28 | Nisus Corporation | Method of treating wood |
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Citations (89)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1388513A (en)* | 1920-08-09 | 1921-08-23 | Asa C Chandler | Process of treating wood |
| US1999458A (en)* | 1934-02-12 | 1935-04-30 | Willoughby F Hollister | Treating method, means, and composition for trees and the like |
| US3007844A (en)* | 1959-04-13 | 1961-11-07 | Allg Holzimpragnierung Dr Wolm | Wood-preserving agent |
| US3321464A (en)* | 1961-06-30 | 1967-05-23 | Du Pont | 3-carbo hydrocarbonoxy amino crotonamides and process for the preparation of uracils therefrom |
| US3443881A (en)* | 1966-05-06 | 1969-05-13 | Monie S Hudson | Method and apparatus for longitudinally impregnating wood |
| US3535423A (en)* | 1965-08-12 | 1970-10-20 | Velsicol Chemical Corp | Wettable powder pesticide concentrate |
| US3622377A (en)* | 1969-08-27 | 1971-11-23 | Us Agriculture | Process for applying copper 8-quinolinolate to cellulosics from solvent system |
| US3816307A (en)* | 1970-07-13 | 1974-06-11 | W Woods | Fire retardant resins |
| US3837875A (en)* | 1973-01-19 | 1974-09-24 | J Murphy | Composition for cleaning, sealing, preserving, protecting and beautifying host materials |
| US3945835A (en)* | 1972-12-12 | 1976-03-23 | Canadian Patents And Development Limited | Heavy duty aqueous wood preservative |
| US3957494A (en)* | 1974-09-30 | 1976-05-18 | Koppers Company, Inc. | Chromated copper arsenate wood preservative compositions |
| US3968276A (en)* | 1972-10-25 | 1976-07-06 | Diversified Wood Products, Inc. | Process for the preservation of wood |
| US4003994A (en)* | 1973-05-15 | 1977-01-18 | Texaco Trinidad, Inc. | Copper-alkaline earth metal fungicidal compositions |
| US4058607A (en)* | 1973-07-17 | 1977-11-15 | Airwick Industries, Inc. | Insecticide evaporator comprising a stabilizer |
| US4061770A (en)* | 1976-04-15 | 1977-12-06 | Diamond Shamrock Corporation | Flowable, aqueous pesticide compositions of improved activity |
| US4062991A (en)* | 1973-08-15 | 1977-12-13 | Fosroc A.G. | Treatment of wood |
| US4075325A (en)* | 1976-10-22 | 1978-02-21 | Gabriel Peter Kauzal | Veterinary lick preparation |
| US4142009A (en)* | 1974-08-13 | 1979-02-27 | Fosroc International Limited | Method of treating timber with composition having a colloidal pigment |
| US4172904A (en)* | 1976-06-15 | 1979-10-30 | Young, Prussin, Mgk, J.V. | Case IV (D) adherent controlled release pesticide |
| US4310590A (en)* | 1979-12-26 | 1982-01-12 | Rohm And Haas Company | 3-Isothiazolones as biocides |
| US4313976A (en)* | 1979-09-07 | 1982-02-02 | Osmose Wood Preserving Co. Of America, Inc. | Composition and process for coloring and preserving wood |
| US4339617A (en)* | 1980-03-31 | 1982-07-13 | Uop Inc. | Hydration of olefins in the presence of a corrosion inhibitor |
| US4404169A (en)* | 1981-11-20 | 1983-09-13 | Norddeutsche Affinerie Ag | Process for producing cupric hydroxide |
| US4507152A (en)* | 1982-09-09 | 1985-03-26 | Mooney Chemicals, Inc. | Fungicidal and insecticidal compositions for treating wood |
| US4622248A (en)* | 1984-04-04 | 1986-11-11 | Osmose Wood Preserving Co. Of America, Inc. | Preservative composition for wood |
| USRE32329E (en)* | 1978-03-20 | 1987-01-13 | Method of adhering mineral deposit in wood fragment surfaces | |
| US4649065A (en)* | 1985-07-08 | 1987-03-10 | Mooney Chemicals, Inc. | Process for preserving wood |
| US4663364A (en)* | 1984-09-05 | 1987-05-05 | Kao Corporation | Biocidal fine powder, its manufacturing method and a suspension for agricultural use containing the above powder |
| US4670430A (en)* | 1983-07-06 | 1987-06-02 | Kao Corporation | Finely powdered polyvalent metal salts of 2-mercaptopyridine-N-oxide, method for producing the same, and antibacterial compositions comprising the same |
| US4737491A (en)* | 1984-06-20 | 1988-04-12 | Kemira Oy | Wood preservative |
| US4741971A (en)* | 1986-05-23 | 1988-05-03 | The Dow Chemical Company | Method for imparting flame resistance to wood surfaces |
| US4808406A (en)* | 1984-12-05 | 1989-02-28 | Kocide Chemical Corporation | Preparation of cupric hydroxide compositions |
| US4857365A (en)* | 1987-02-24 | 1989-08-15 | Matsushita Electric Works, Ltd. | Method of manufacturing modified wood material |
| US4897427A (en)* | 1987-01-14 | 1990-01-30 | Sandoz Ltd. | Method of combatting pruning wound diseases |
| US4923894A (en)* | 1985-04-10 | 1990-05-08 | Nippon Paint Co., Ltd. | Polymeric microparticles having pesticidal activity |
| US4988545A (en)* | 1989-08-17 | 1991-01-29 | Board Of Control Of Michigan Technological University | Method for treating wood against fungal attack |
| US5049677A (en)* | 1989-05-24 | 1991-09-17 | Rohm And Haas Company | Bismuth salt stabilizers for 3-isothiazolones |
| US5145684A (en)* | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| US5147686A (en)* | 1988-03-17 | 1992-09-15 | Ishihara Sangyo Kaisha, Ltd. | Method of making titanium oxide powder having antimicrobial metal supported thereon |
| US5186947A (en)* | 1990-10-20 | 1993-02-16 | Dr. Wolman Gmbh | Wood preservative based on polymeric nitrogen compounds and metal-fixing acids |
| US5196407A (en)* | 1990-05-23 | 1993-03-23 | Desowag Materialschutz Gmbh | Composition for preserving wood and wood materials |
| US5200421A (en)* | 1991-04-23 | 1993-04-06 | Bayer Aktiengesellschaft | Microbicidal active compound combinations |
| US5277979A (en)* | 1987-08-26 | 1994-01-11 | Rohm And Haas Company | Process for microencapsulation |
| US5304376A (en)* | 1989-02-03 | 1994-04-19 | Shell Internationale Research Maatschappij B.V. | Fungicidal composition |
| US5342438A (en)* | 1993-02-04 | 1994-08-30 | West Michael H | Remedial wood preservative |
| US5360783A (en)* | 1989-07-26 | 1994-11-01 | Takemoto Yushi Kabushiki Kaisha | Water-based pesticidal composition |
| US5424077A (en)* | 1993-07-13 | 1995-06-13 | Church & Dwight Co., Inc. | Co-micronized bicarbonate salt compositions |
| US5426121A (en)* | 1994-10-04 | 1995-06-20 | Akzo Nobel N.V. | Wood preservation formulation comprising complex of a copper cation and alkoxylated diamine |
| US5438034A (en)* | 1993-06-09 | 1995-08-01 | Lonza, Inc. | Quaternary ammonium carbonate compositions and preparation thereof |
| US5462589A (en)* | 1994-02-22 | 1995-10-31 | Mississippi Forest Products Laboratory | Synergistic wood preservative compositions |
| US5462931A (en)* | 1992-06-25 | 1995-10-31 | Rohm And Haas Company | Fungicidal 2-heterocyclic-2,2-disubstituted-ethyl 1,2,4-triazoles |
| US5484934A (en)* | 1992-12-30 | 1996-01-16 | Nihon Nohyaku Co., Ltd. | Isothiazole derivatives, a process for production thereof and uses thereof |
| US5527423A (en)* | 1994-10-06 | 1996-06-18 | Cabot Corporation | Chemical mechanical polishing slurry for metal layers |
| US5527816A (en)* | 1991-08-26 | 1996-06-18 | Rohm And Haas Company | Fungicidal 2-aryl-2-cyano-2-(aryloxyalkyl)ethyl-1,2-4-triazoles |
| US5527384A (en)* | 1991-08-01 | 1996-06-18 | Hickson International, Plc | Preservatives for wood and other cellulosic materials |
| US5536305A (en)* | 1994-06-08 | 1996-07-16 | Yu; Bing | Low leaching compositions for wood |
| US5552378A (en)* | 1990-03-06 | 1996-09-03 | The Procter & Gamble Company | Solid consumer product compositions containing small particle cyclodextrin complexes |
| US5635217A (en)* | 1991-04-18 | 1997-06-03 | Dr. Wolman Gmbh | Wood preservatives |
| US5667795A (en)* | 1994-02-07 | 1997-09-16 | Isk Biosciences Corporation | Pesticidal micronutrient compositions containing zinc oxide |
| US5714507A (en)* | 1994-07-01 | 1998-02-03 | Janssen Pharmaceutica, N.V. | Synergistic compositions containing metconazole and another triazole |
| US5763364A (en)* | 1994-09-21 | 1998-06-09 | Hoechst Schering Agrevo Gmbh | Thixotropic aqueous plant protection agent suspensions |
| US5833741A (en)* | 1997-01-16 | 1998-11-10 | Lonza Inc. | Waterproofing and preservative compositons for wood |
| US5874456A (en)* | 1992-02-05 | 1999-02-23 | Novartis Ag | Fungicidal compositions |
| US5874025A (en)* | 1995-04-12 | 1999-02-23 | Bayer Aktiengesellschaft | Timber preservative containing a copper compound |
| US5874476A (en)* | 1997-07-14 | 1999-02-23 | Rohm And Haas Company | Dihaloformaldoxime carbamates as antimicrobial agents |
| US5879025A (en)* | 1996-08-08 | 1999-03-09 | Trw Vehicle Safety Systems Inc. | Inflator for an inflatable vehicle occupant protection device |
| US5972266A (en)* | 1998-02-26 | 1999-10-26 | Trus Joist Macmillan A Limited Partnership | Composite products |
| US5990043A (en)* | 1993-12-21 | 1999-11-23 | Bayer Aktiengesellschaft | Anti-fouling compositions |
| US6521288B2 (en)* | 2000-05-31 | 2003-02-18 | Board Of Control Of Michigan Technological University | Compositions and methods for wood preservation |
| US20040176477A1 (en)* | 2003-03-06 | 2004-09-09 | The Procter & Gamble Company | Chitosan powder |
| US20040258768A1 (en)* | 2003-06-17 | 2004-12-23 | Richardson H. Wayne | Particulate wood preservative and method for producing same |
| US20040258838A1 (en)* | 2003-06-17 | 2004-12-23 | Richardson H. Wayne | Method for preserving wood materials using precipitated copper compounds |
| US20040258767A1 (en)* | 2003-04-09 | 2004-12-23 | Leach Robert M. | Micronized wood preservative formulations |
| US6843837B2 (en)* | 2002-07-26 | 2005-01-18 | Osmose, Inc. | Polymeric wood preservative compositions |
| US20050013939A1 (en)* | 2001-06-15 | 2005-01-20 | Peter Vinden | Boron-based wood preservatives and treatment of wood with boron-based preservatives |
| US20050107467A1 (en)* | 2003-10-17 | 2005-05-19 | Richardson H. W. | Methods for producing and using a Cu(I)-based wood preservative |
| US6905532B2 (en)* | 2002-02-14 | 2005-06-14 | Phibro-Tech, Inc. | Process for the dissolution of copper metal |
| US20050130866A1 (en)* | 2002-02-14 | 2005-06-16 | Richardson Hugh W. | Process for the dissolution of copper metal |
| US20050182152A1 (en)* | 2002-06-06 | 2005-08-18 | Ralph Nonninger | Antimicrobial polymeric coating composition |
| US20050256026A1 (en)* | 2004-05-17 | 2005-11-17 | Hodge Robert L | Compatibilizing surfactant useful with slurries of copper particles |
| US20050255251A1 (en)* | 2004-05-17 | 2005-11-17 | Hodge Robert L | Composition, method of making, and treatment of wood with an injectable wood preservative slurry having biocidal particles |
| US20050252408A1 (en)* | 2004-05-17 | 2005-11-17 | Richardson H W | Particulate wood preservative and method for producing same |
| US20060062926A1 (en)* | 2004-05-17 | 2006-03-23 | Richardson H W | Use of sub-micron copper salt particles in wood preservation |
| US20060076686A1 (en)* | 2003-02-26 | 2006-04-13 | Tuominen Risto | Method for manufacturing an electronic module, and an electronic module |
| US20060075921A1 (en)* | 2004-10-08 | 2006-04-13 | Richardson Hugh W | Milled submicron chlorothalonil with narrow particle size distribution, and uses thereof |
| US20060075923A1 (en)* | 2004-10-12 | 2006-04-13 | Richardson H W | Method of manufacture and treatment of wood with injectable particulate iron oxide |
| US20060086841A1 (en)* | 2004-10-08 | 2006-04-27 | Richardson H W | Milled submicron organic biocides with narrow particle size distribution, and uses thereof |
| US20070193473A1 (en)* | 2003-04-09 | 2007-08-23 | Jun Zhang | Micronized wood presservative formulations |
| US20080199535A1 (en)* | 2004-12-09 | 2008-08-21 | The Dial Corporation | Compositions Having a High Antiviral and Antibacterial Efficacy |
Family Cites Families (144)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB812408A (en) | 1955-04-22 | 1959-04-22 | Gerald Gobert | A composition of matter for the preservation of wood |
| DE1531868U (en) | ||||
| GB222268A (en) | 1923-08-04 | 1924-10-02 | Heinrich Vogel | An improved process for the manufacture of an arsenical preparation for exterminating or keeping down pests |
| US2558304A (en) | 1948-03-11 | 1951-06-26 | American Cyanamid Co | Production of iron oxide pigments |
| NL213227A (en)* | 1956-11-12 | |||
| NL276056A (en) | 1961-03-18 | |||
| US3087936A (en) | 1961-08-18 | 1963-04-30 | Lubrizol Corp | Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound |
| BE795961A (en) | 1972-02-25 | 1973-08-27 | Hoechst Ag | APPLICATION OF SULPHURIC HEMI-ESTERS TO DISPERSION OF COLORANTS |
| SE379167B (en) | 1973-03-15 | 1975-09-29 | Bp Svenska | |
| US4075326A (en) | 1973-12-22 | 1978-02-21 | Rohm And Haas Company | Fungicidal/algicidal composition for non-medical uses |
| DE2513076C3 (en) | 1975-03-25 | 1980-11-27 | Dr. Wolman Gmbh, 7573 Sinzheim | Wood preservative solution containing colorant |
| DE2531895C2 (en) | 1975-07-17 | 1984-07-26 | Hoechst Ag, 6230 Frankfurt | Use of aqueous plastic dispersions for impregnating and priming absorbent substrates |
| SU642166A1 (en) | 1976-06-21 | 1979-01-15 | Латвийский Научно-Исследовательский Институт Лесохозяйственных Проблем | Method of improving timber quality |
| GB1491330A (en) | 1976-07-14 | 1977-11-09 | Imp Group Ltd | Method of treating a wooden article with a fungicide |
| US4081050A (en) | 1977-02-02 | 1978-03-28 | International Harvester Company | Front engine tractor having transverse midship mounted heat exchanger |
| GB1574939A (en) | 1977-05-12 | 1980-09-10 | Cuprinol Ltd | Compositions containing preservative metals and their use for the preservation of wood and like materials and as fungicides |
| US4220688A (en) | 1978-08-31 | 1980-09-02 | Ralph Mitchell | Protecting wood from wood degrading organisms |
| US4650792A (en) | 1980-07-18 | 1987-03-17 | Dennis Underwood | Mosquito abatement |
| DE3137808A1 (en) | 1981-09-23 | 1983-03-31 | Merck Patent Gmbh, 6100 Darmstadt | PEARL SHINE PIGMENTS WITH IMPROVED LIGHT FASTNESS, METHOD FOR THE PRODUCTION AND USE |
| US4596694A (en) | 1982-09-20 | 1986-06-24 | Kelsey-Hayes Company | Method for hot consolidating materials |
| US4597730A (en) | 1982-09-20 | 1986-07-01 | Kelsey-Hayes Company | Assembly for hot consolidating materials |
| US5098472A (en) | 1983-06-17 | 1992-03-24 | Commonwealth Scientific & Industrial Research Organization | Preservative composition |
| WO1985000040A1 (en) | 1983-06-17 | 1985-01-03 | Koppers Australia Pty. Limited | Preservative composition |
| JPS60155403A (en) | 1983-08-30 | 1985-08-15 | 神東塗料株式会社 | Aqueous suspending wood protective composition |
| JPS6089422A (en) | 1983-10-24 | 1985-05-20 | Kureha Chem Ind Co Ltd | Remedy for osteoporosis |
| FR2562081B1 (en) | 1984-03-27 | 1986-10-10 | Thann Mulhouse Sa | PROCESS FOR THE PREPARATION OF RED PIGMENTARY IRON OXIDES FROM RESIDUAL FERROUS SULFATE |
| US4539047A (en) | 1984-04-12 | 1985-09-03 | Desoto, Inc. | Clear coatings to protect wood from discoloring and greying on exterior exposure |
| JPS61194091A (en) | 1985-02-21 | 1986-08-28 | Dainichi Seika Kogyo Kk | Phosphate ester pigment dispersant |
| US4720514A (en) | 1985-03-11 | 1988-01-19 | Phillips Petroleum Company | Pigment concentrates for resins |
| JPS61246002A (en)* | 1985-04-24 | 1986-11-01 | 松下電工株式会社 | Manufacture of improved wood |
| JPS6239201A (en) | 1985-08-15 | 1987-02-20 | 松下電工株式会社 | Manufacture of improved wood |
| JPS62116102A (en) | 1985-11-15 | 1987-05-27 | 松下電工株式会社 | Improved wood |
| DE3542441A1 (en) | 1985-11-30 | 1987-06-04 | Hoechst Ag | Bisphosphoric acid monoesters of alkylene oxide block copolymers, and salts thereof |
| US4713195A (en) | 1986-01-30 | 1987-12-15 | Aqua-Chem Inc. | Scale inhibitor |
| US4950221A (en) | 1986-07-18 | 1990-08-21 | Gordon Robert T | Process for affecting molecules in tissue |
| DE3627023A1 (en) | 1986-08-09 | 1988-02-11 | Hoechst Ag | PIGMENT DISPERSIONS, METHOD FOR THEIR PRODUCTION AND THEIR USE |
| US4752297A (en) | 1987-02-26 | 1988-06-21 | Osmose Wood Preserving, Inc. | Process for coloring wood with iron salt in water |
| JPH082524B2 (en) | 1987-07-22 | 1996-01-17 | 宏人 勝部 | Method for producing modified wood |
| ES2006347A6 (en) | 1988-03-03 | 1989-04-16 | Colores Hispania | A corrosion inhibiting pigment and a process for the manufacturing thereof. |
| US5198133A (en) | 1988-03-14 | 1993-03-30 | Ethyl Petroleum Additives, Inc. | Modified succinimide or sucinamide dispersants and their production |
| NZ225428A (en) | 1988-07-15 | 1991-03-26 | Chemicca Ltd | Wood treatment composition containing two different fungicides; concentrate capable of dilution with water |
| US4857214A (en) | 1988-09-16 | 1989-08-15 | Ethylk Petroleum Additives, Inc. | Oil-soluble phosphorus antiwear additives for lubricants |
| US4872916A (en) | 1988-09-22 | 1989-10-10 | Sun Chemical Corporation | Phosphate ester pigment dispersant |
| US4961865A (en) | 1988-12-30 | 1990-10-09 | United American, Inc. | Combustion inhibiting methods and compositions |
| US5470585A (en) | 1989-01-27 | 1995-11-28 | Giltech Limited | Medicinal substance for topical application |
| DE3930687A1 (en) | 1989-09-14 | 1991-04-11 | Byk Chemie Gmbh | Phosphoric acid esters, process for their preparation and their use as dispersing agents |
| US5151218A (en) | 1989-09-14 | 1992-09-29 | Byk-Chemie Gmbh | Phosphoric acid esters, method of producing them, and use thereof as dispersants |
| US5207823A (en) | 1990-04-03 | 1993-05-04 | Kabushiki Kaisha Koshii Preserving | Wood preservative composition and process for treating wood with the same |
| CA2040279C (en) | 1990-08-14 | 1999-10-12 | John F. Grunewalder | Water-borne treatment compositions for porous substrates |
| US6471976B1 (en) | 1990-10-01 | 2002-10-29 | Evelyn J. Taylor | Copper complex bactericide/fungicide and method of making same |
| US5110822A (en) | 1991-01-03 | 1992-05-05 | Rohm And Haas Company | Synergistic combinations of 4,5-dichloro-2-n-octyl-3-isothiazolone or 2-methyl-3-isothiazolone with ferric dimethyl dithiocarbamate fungicide |
| DK172239B1 (en) | 1991-05-07 | 1998-02-02 | Ulrich Schirnig | Process for quality improvement, such as improved preservation, of wood blanks by impregnating them |
| US6306201B1 (en) | 1992-01-29 | 2001-10-23 | I.B.E. Company, Ltd. | Bivalent iron compounds |
| DE4222410C2 (en) | 1992-07-08 | 1995-02-09 | Schulz Gmbh & Co Kg Farben Und | Beeswax-containing wood glaze |
| PL169344B1 (en) | 1992-11-24 | 1996-07-31 | Inst Chemii Nieorganicznej | Wood impregnation agent and the method of its production |
| US5478598A (en) | 1993-07-28 | 1995-12-26 | Kabushiki Kaisha Koshii Preserving | Wood preservative composition, process for treating wood with the same, wood treated with the same |
| GB9319129D0 (en) | 1993-09-15 | 1993-11-03 | Dowelanco Ltd | Storage and dilution of stable aqueous dispersions |
| DE4410727A1 (en) | 1994-03-28 | 1995-10-05 | Sued Chemie Ag | Thickener based on at least one synthetic layered silicate |
| DK170980B1 (en) | 1994-04-07 | 1996-04-09 | Smith Hansen Arne | Wood impregnation agent, ready-to-use impregnation solution and use of the agent |
| JP3109101B2 (en) | 1994-10-05 | 2000-11-13 | 東陶機器株式会社 | Antimicrobial solid, method for producing the same, and method for using the same |
| JPH08183010A (en) | 1994-12-27 | 1996-07-16 | Daiken Trade & Ind Co Ltd | Method for producing modified wood |
| GB9502253D0 (en) | 1995-02-06 | 1995-03-29 | Giltech Ltd | The effects of antibacterial agents on the behaviour of mouse fibroblasts in vitro |
| DE19511624A1 (en) | 1995-03-30 | 1996-10-02 | Bayer Ag | Aqueous pigment preparations |
| KR100445863B1 (en) | 1995-09-29 | 2004-11-26 | 롬 앤드 하스 캄파니 | Wood preservative |
| NZ280716A (en) | 1995-12-20 | 1999-02-25 | Nigel Paul Maynard | Method for dissolution of insoluble biocides using an onium compound |
| DE19608435A1 (en) | 1996-03-05 | 1997-09-11 | Wolman Gmbh Dr | Wood preservative for after-protection |
| US6342556B1 (en) | 1996-04-16 | 2002-01-29 | Foster Products | Ultra violet light protective coating |
| AU2387297A (en) | 1996-04-19 | 1997-11-12 | Dr. Wolman Gmbh | Process for treating wood against infection by moulds harmful to wood |
| WO1998005206A1 (en) | 1996-08-02 | 1998-02-12 | Hickson International Plc | Quaternary ammonium salt compositions, and methods for treating substrates |
| US6139879A (en) | 1997-06-25 | 2000-10-31 | Foliar Nutrients, Inc. | Fungicidal and bactericidal compositions for plants containing compounds in the form of heavy metal chelates |
| US6344271B1 (en) | 1998-11-06 | 2002-02-05 | Nanoenergy Corporation | Materials and products using nanostructured non-stoichiometric substances |
| AU733806B2 (en) | 1996-10-22 | 2001-05-24 | Mywood Kabushiki Kaisha | Method of impregnating wood with liquid |
| US6235916B1 (en) | 1996-12-24 | 2001-05-22 | University Of Southern Mississippi | Internally plasticizing and crosslinkable monomers and applications thereof |
| EP0966341B1 (en) | 1997-03-06 | 2002-10-02 | Dr. Wolman GmbH | Wood preservative for subsequent application |
| JPH10272610A (en) | 1997-03-29 | 1998-10-13 | Kyodo Kumiai Bio Raitoyuugou | Wood having capability for sterilizing wood-rotting fungus and manufacture thereof |
| CA2311583A1 (en)* | 1997-11-26 | 1999-06-03 | Showa Denko K.K. | Method for the treatment of wood with metallic treatment and wood treated by the method |
| CA2323904A1 (en) | 1998-03-20 | 1999-09-30 | John Bernard Watkins | Composition for impregnating porous materials, preparation and use thereof |
| AR019119A1 (en)* | 1998-04-29 | 2001-12-26 | Nz Forest Research Inst Ltd | A METHOD FOR INHIBITING THE FUNGICAL ATTACK AND COMPOSITIONS TO USE WITH THIS METHOD |
| GB9813271D0 (en) | 1998-06-19 | 1998-08-19 | Zeneca Ltd | Composition and use |
| EP1089986B1 (en) | 1998-06-22 | 2005-03-30 | Ciba SC Holding AG | Poly-trisaryl-1,3,5-triazine carbamate ultraviolet light absorbers |
| FR2780281B1 (en) | 1998-06-26 | 2000-08-18 | Oreal | COMPOSITIONS COMPRISING IRON OXIDE NANOPIGMENTS FOR ARTIFICIAL SKIN COLORING AND USES THEREOF |
| DE19834028A1 (en) | 1998-07-28 | 2000-02-03 | Wolman Gmbh Dr | Process for treating wood against infestation by wood-damaging fungi |
| AUPP518398A0 (en) | 1998-08-11 | 1998-09-03 | Young, Colin Leslie Professor | Durable mollusc repellent |
| JP2000102907A (en) | 1998-09-30 | 2000-04-11 | Takahashi Kikan:Kk | Method for producing mineral-filled wood and mineral-filled wood |
| FR2784860B1 (en) | 1998-10-26 | 2000-12-29 | Action Pin | LIQUID COMPOSITION HAVING FUNGICIDAL, BACTERICIDAL OR BACTERIOSTATIC ACTIVITY AND METHODS OF PREPARING AND USING THE SAME |
| JP2002528569A (en) | 1998-10-27 | 2002-09-03 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | In situ polymerization of a fluoropolymer in a porous matrix |
| JP2000141316A (en) | 1998-11-09 | 2000-05-23 | Showa Denko Kk | Modified wood and its manufacture |
| US6274199B1 (en)* | 1999-01-19 | 2001-08-14 | Chemical Specialties, Inc. | Wood treatment process |
| ATE333350T1 (en) | 1999-04-08 | 2006-08-15 | Lonza Ag | METHOD FOR IMPROVING THE PENETRATION OF WOOD PRESERVATIVES INTO WOOD |
| AU4225700A (en) | 1999-04-12 | 2000-11-14 | Dow Agrosciences Llc | Aqueous dispersions of agricultural chemicals |
| US20010051175A1 (en) | 1999-04-12 | 2001-12-13 | Strom Robert M. | Aqueous dispersions of agricultural chemicals |
| EP1066825A1 (en) | 1999-06-17 | 2001-01-10 | The Procter & Gamble Company | An anti-microbial body care product |
| DK1194485T3 (en) | 1999-07-09 | 2004-08-09 | Ciba Sc Holding Ag | New pigment form of Pigment Violet 23 |
| US6475631B1 (en) | 1999-07-15 | 2002-11-05 | Toagosei Co., Ltd. | Antimicrobial agent, antimicrobial resin composition and antimicrobial artificial marble |
| JP2001121512A (en) | 1999-10-29 | 2001-05-08 | Xyence Corp | Copper based wood-preserving composition |
| US6303183B1 (en) | 1999-11-08 | 2001-10-16 | Aos Holding Company | Anti-microbial porcelain enamel coating |
| DE19953775A1 (en) | 1999-11-09 | 2001-05-10 | Bayer Ag | Active ingredient combinations with insecticidal and acaricidal properties |
| DE19961621C2 (en) | 1999-12-13 | 2002-11-14 | Schuelke & Mayr Gmbh | Bactericidal and fungicidal liquid preparations for technical products |
| JP2001247333A (en) | 1999-12-28 | 2001-09-11 | Ishizuka Glass Co Ltd | Antibacterial glass composition, antibacterial fiber, antibacterial twisted yarn and antibacterial cloth |
| GB9930750D0 (en) | 1999-12-29 | 2000-02-16 | Novartis Ag | Organic compounds |
| ES2303527T3 (en) | 2000-05-10 | 2008-08-16 | Jagotec Ag | GRINDING PROCEDURE. |
| WO2002006417A1 (en) | 2000-07-17 | 2002-01-24 | U.S. Borax Inc. | Mixed solubility borate preservative |
| AU2001274927B2 (en) | 2000-05-24 | 2006-11-23 | Lonza Inc. | Amine oxide wood preservatives |
| DE10029648C1 (en) | 2000-06-15 | 2002-02-07 | Goldschmidt Ag Th | Block copolymers of phosphoric acid esters, their salts and their use as emulsifiers and dispersants |
| SI1294358T1 (en) | 2000-06-28 | 2004-12-31 | Smithkline Beecham Plc | Wet milling process |
| US6306202B1 (en)* | 2000-06-30 | 2001-10-23 | Michael Howard West | Water soluble fixed copper-borax wood preservative composition |
| JP4799776B2 (en) | 2000-08-22 | 2011-10-26 | 富士フイルム株式会社 | Electrolyte composition and electrochemical cell using the same |
| NZ525028A (en) | 2000-08-31 | 2005-07-29 | Skyepharma Canada Inc | Milled particles |
| ATE328479T1 (en) | 2000-09-21 | 2006-06-15 | Ciba Sc Holding Ag | MIXTURES OF PHENOLIC AND INORGANIC MATERIALS THAT EXHIBIT ANTIMICROBIAL ACTIVITY |
| US6514512B1 (en) | 2000-10-02 | 2003-02-04 | Engelhard Corporation | Pesticide delivery system |
| US6867250B1 (en) | 2000-10-30 | 2005-03-15 | Cytec Technology Corp. | Non-yellowing ortho-dialkyl aryl substituted triazine ultraviolet light absorbers |
| US6537670B1 (en) | 2000-11-03 | 2003-03-25 | Cytec Technology Corp. | Bis(alkyleneoxybenzophenone) ultraviolet light absorbers |
| JP4848583B2 (en) | 2000-11-21 | 2011-12-28 | 大日本印刷株式会社 | Method for producing film having hard coat layer |
| DE50115774D1 (en) | 2000-11-22 | 2011-02-24 | Strack H C Clevios Gmbh | DISPERSIBLE POLYMER POWDER |
| US6664327B2 (en) | 2001-01-10 | 2003-12-16 | Rohm And Haas Company | Aqueous composition for wood stain |
| KR100852190B1 (en) | 2001-02-08 | 2008-08-14 | 시바 홀딩 인크 | A method for the preparation of a conditioned pigment |
| US6596246B2 (en) | 2001-03-20 | 2003-07-22 | Dermet Sa De Cv | Process for producing stable cupric hydroxide and basic cupric salts |
| AU2002258649A1 (en) | 2001-03-30 | 2002-10-28 | Rhodia Inc. | Aqeuous suspension of nanoparticles comprising an agrochemical active ingredient |
| EP1249165B1 (en) | 2001-04-11 | 2004-09-15 | Japan EnviroChemicals, Ltd. | A wood preservative |
| US20030010956A1 (en) | 2001-06-13 | 2003-01-16 | Allan Las | Wood preservative composition |
| US6753016B2 (en) | 2001-07-03 | 2004-06-22 | Rohm And Haas Company | Preservation of wood products |
| US6624242B2 (en) | 2001-08-08 | 2003-09-23 | Isp Investments Inc. | Aqueous dispersions of low-molecular weight, low-melting and water insoluble polymers |
| US7019046B2 (en) | 2001-08-08 | 2006-03-28 | Isp Investments Inc. | Aqueous suspension agent for water insoluble compounds |
| CA2357357C (en) | 2001-09-17 | 2010-03-16 | Genics Inc. | Method of treating building materials with boron and building materials |
| EP1298092A1 (en) | 2001-09-28 | 2003-04-02 | Spiess -Urania Chemicals GmbH | Controlled morphogenesis of copper salts |
| US6686056B2 (en) | 2001-12-04 | 2004-02-03 | Chemical Specialties, Inc. | Reactive oil/copper preservative systems for wood products |
| US20030170317A1 (en) | 2002-01-16 | 2003-09-11 | Smt, Inc. | Flame retardant and microbe inhibiting methods and compositions |
| JP2003266406A (en) | 2002-03-19 | 2003-09-24 | Kazunobu Shiozawa | Method of treating timber for highly fixable antiseptic finish and mothproof finish and its treating timber |
| US6579354B1 (en) | 2003-01-13 | 2003-06-17 | Michael Howard West | Acidic copper—aluminum nitrate wood preservative |
| US20060257578A1 (en) | 2003-04-09 | 2006-11-16 | Jun Zhang | Micronized wood preservative formulations comprising boron compounds |
| US8747908B2 (en) | 2003-04-09 | 2014-06-10 | Osmose, Inc. | Micronized wood preservative formulations |
| US6887400B1 (en) | 2003-10-30 | 2005-05-03 | Nalco Company | Water-soluble polyaminoamides comprising 1,3-diimines as sunscreen agents |
| CA2547817A1 (en) | 2003-12-08 | 2005-06-23 | Osmose, Inc. | Composition and process for coloring and preserving wood |
| AU2005237592A1 (en) | 2004-04-27 | 2005-11-10 | Osmose, Inc. | Micronized organic preservative formulations |
| US20070131136A1 (en) | 2004-04-27 | 2007-06-14 | Osmose, Inc. | Composition And Process For Coloring Wood |
| US20060147632A1 (en) | 2004-04-27 | 2006-07-06 | Jun Zhang | Composition and process for coloring and preserving wood |
| AU2005246264A1 (en) | 2004-05-13 | 2005-12-01 | Osmose, Inc. | Compositions and methods for treating cellulose-based materials with micronized additives |
| WO2005110692A2 (en) | 2004-05-17 | 2005-11-24 | Phibro-Tech, Inc. | Composition, method of making, and treatment of wood with an injectable wood preservative slurry having biocidal particles |
| US20060078686A1 (en) | 2004-10-08 | 2006-04-13 | Hodge Robert L | Penetration of copper-ethanolamine complex in wood |
| US20060086284A1 (en) | 2004-10-14 | 2006-04-27 | Jun Zhang | Non-alkaline micronized wood preservative formulations |
| NZ554680A (en) | 2004-10-14 | 2010-10-29 | Osmose Inc | Micronized wood preservative formulations in organic carriers |
| US20060288904A1 (en) | 2005-06-21 | 2006-12-28 | Leach Robert M | Micronized wood preservative compositions |
| WO2007014012A2 (en) | 2005-07-21 | 2007-02-01 | Osmose, Inc. | Compositions and methods for wood preservation |
| US20070259016A1 (en) | 2006-05-05 | 2007-11-08 | Hodge Robert L | Method of treating crops with submicron chlorothalonil |
- 2005
- 2005-10-05NZNZ554680Apatent/NZ554680A/enunknown
- 2005-10-05CACA002584254Apatent/CA2584254A1/ennot_activeAbandoned
- 2005-10-05USUS11/243,640patent/US20060112850A1/ennot_activeAbandoned
- 2005-10-05SISI200531687Tpatent/SI1799776T1/enunknown
- 2005-10-05EPEP11179103.4Apatent/EP2431430B1/ennot_activeExpired - Lifetime
- 2005-10-05EPEP05801806Apatent/EP1799776B1/ennot_activeExpired - Lifetime
- 2005-10-05BRBRPI0518154-2Apatent/BRPI0518154A/ennot_activeIP Right Cessation
- 2005-10-05PLPL11179103Tpatent/PL2431430T3/enunknown
- 2005-10-05AUAU2005296077Apatent/AU2005296077B2/ennot_activeExpired
- 2005-10-05WOPCT/US2005/035946patent/WO2006044218A2/enactiveApplication Filing
- 2005-10-13GTGT200500289Apatent/GT200500289A/enunknown
- 2005-10-14ARARP050104321Apatent/AR053648A1/enactiveIP Right Grant
- 2005-10-14TWTW094135917Apatent/TW200632058A/enunknown
- 2005-10-14HNHN2005000803Apatent/HN2005000803A/enunknown
- 2011
- 2011-06-16USUS13/161,772patent/US9775350B2/enactiveActive
- 2017
- 2017-08-29USUS15/689,728patent/US20170360042A1/ennot_activeAbandoned
Patent Citations (99)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1388513A (en)* | 1920-08-09 | 1921-08-23 | Asa C Chandler | Process of treating wood |
| US1999458A (en)* | 1934-02-12 | 1935-04-30 | Willoughby F Hollister | Treating method, means, and composition for trees and the like |
| US3007844A (en)* | 1959-04-13 | 1961-11-07 | Allg Holzimpragnierung Dr Wolm | Wood-preserving agent |
| US3321464A (en)* | 1961-06-30 | 1967-05-23 | Du Pont | 3-carbo hydrocarbonoxy amino crotonamides and process for the preparation of uracils therefrom |
| US3535423A (en)* | 1965-08-12 | 1970-10-20 | Velsicol Chemical Corp | Wettable powder pesticide concentrate |
| US3443881A (en)* | 1966-05-06 | 1969-05-13 | Monie S Hudson | Method and apparatus for longitudinally impregnating wood |
| US3622377A (en)* | 1969-08-27 | 1971-11-23 | Us Agriculture | Process for applying copper 8-quinolinolate to cellulosics from solvent system |
| US3816307A (en)* | 1970-07-13 | 1974-06-11 | W Woods | Fire retardant resins |
| US3968276A (en)* | 1972-10-25 | 1976-07-06 | Diversified Wood Products, Inc. | Process for the preservation of wood |
| US3945835A (en)* | 1972-12-12 | 1976-03-23 | Canadian Patents And Development Limited | Heavy duty aqueous wood preservative |
| US3837875A (en)* | 1973-01-19 | 1974-09-24 | J Murphy | Composition for cleaning, sealing, preserving, protecting and beautifying host materials |
| US4003994A (en)* | 1973-05-15 | 1977-01-18 | Texaco Trinidad, Inc. | Copper-alkaline earth metal fungicidal compositions |
| US4058607A (en)* | 1973-07-17 | 1977-11-15 | Airwick Industries, Inc. | Insecticide evaporator comprising a stabilizer |
| US4062991A (en)* | 1973-08-15 | 1977-12-13 | Fosroc A.G. | Treatment of wood |
| US4142009A (en)* | 1974-08-13 | 1979-02-27 | Fosroc International Limited | Method of treating timber with composition having a colloidal pigment |
| US3957494A (en)* | 1974-09-30 | 1976-05-18 | Koppers Company, Inc. | Chromated copper arsenate wood preservative compositions |
| US4061770A (en)* | 1976-04-15 | 1977-12-06 | Diamond Shamrock Corporation | Flowable, aqueous pesticide compositions of improved activity |
| US4172904A (en)* | 1976-06-15 | 1979-10-30 | Young, Prussin, Mgk, J.V. | Case IV (D) adherent controlled release pesticide |
| US4075325A (en)* | 1976-10-22 | 1978-02-21 | Gabriel Peter Kauzal | Veterinary lick preparation |
| USRE32329E (en)* | 1978-03-20 | 1987-01-13 | Method of adhering mineral deposit in wood fragment surfaces | |
| US4313976A (en)* | 1979-09-07 | 1982-02-02 | Osmose Wood Preserving Co. Of America, Inc. | Composition and process for coloring and preserving wood |
| US4310590A (en)* | 1979-12-26 | 1982-01-12 | Rohm And Haas Company | 3-Isothiazolones as biocides |
| US4339617A (en)* | 1980-03-31 | 1982-07-13 | Uop Inc. | Hydration of olefins in the presence of a corrosion inhibitor |
| US4404169A (en)* | 1981-11-20 | 1983-09-13 | Norddeutsche Affinerie Ag | Process for producing cupric hydroxide |
| US4507152A (en)* | 1982-09-09 | 1985-03-26 | Mooney Chemicals, Inc. | Fungicidal and insecticidal compositions for treating wood |
| US4670430A (en)* | 1983-07-06 | 1987-06-02 | Kao Corporation | Finely powdered polyvalent metal salts of 2-mercaptopyridine-N-oxide, method for producing the same, and antibacterial compositions comprising the same |
| US4622248A (en)* | 1984-04-04 | 1986-11-11 | Osmose Wood Preserving Co. Of America, Inc. | Preservative composition for wood |
| US4737491A (en)* | 1984-06-20 | 1988-04-12 | Kemira Oy | Wood preservative |
| US4663364A (en)* | 1984-09-05 | 1987-05-05 | Kao Corporation | Biocidal fine powder, its manufacturing method and a suspension for agricultural use containing the above powder |
| US4808406A (en)* | 1984-12-05 | 1989-02-28 | Kocide Chemical Corporation | Preparation of cupric hydroxide compositions |
| US4923894A (en)* | 1985-04-10 | 1990-05-08 | Nippon Paint Co., Ltd. | Polymeric microparticles having pesticidal activity |
| US4649065A (en)* | 1985-07-08 | 1987-03-10 | Mooney Chemicals, Inc. | Process for preserving wood |
| US4741971A (en)* | 1986-05-23 | 1988-05-03 | The Dow Chemical Company | Method for imparting flame resistance to wood surfaces |
| US4897427A (en)* | 1987-01-14 | 1990-01-30 | Sandoz Ltd. | Method of combatting pruning wound diseases |
| US4857365A (en)* | 1987-02-24 | 1989-08-15 | Matsushita Electric Works, Ltd. | Method of manufacturing modified wood material |
| US5277979A (en)* | 1987-08-26 | 1994-01-11 | Rohm And Haas Company | Process for microencapsulation |
| US5147686A (en)* | 1988-03-17 | 1992-09-15 | Ishihara Sangyo Kaisha, Ltd. | Method of making titanium oxide powder having antimicrobial metal supported thereon |
| US5304376A (en)* | 1989-02-03 | 1994-04-19 | Shell Internationale Research Maatschappij B.V. | Fungicidal composition |
| US5049677A (en)* | 1989-05-24 | 1991-09-17 | Rohm And Haas Company | Bismuth salt stabilizers for 3-isothiazolones |
| US5360783A (en)* | 1989-07-26 | 1994-11-01 | Takemoto Yushi Kabushiki Kaisha | Water-based pesticidal composition |
| US4988545A (en)* | 1989-08-17 | 1991-01-29 | Board Of Control Of Michigan Technological University | Method for treating wood against fungal attack |
| US5552378A (en)* | 1990-03-06 | 1996-09-03 | The Procter & Gamble Company | Solid consumer product compositions containing small particle cyclodextrin complexes |
| US5196407A (en)* | 1990-05-23 | 1993-03-23 | Desowag Materialschutz Gmbh | Composition for preserving wood and wood materials |
| US5186947A (en)* | 1990-10-20 | 1993-02-16 | Dr. Wolman Gmbh | Wood preservative based on polymeric nitrogen compounds and metal-fixing acids |
| US5145684A (en)* | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| US5635217A (en)* | 1991-04-18 | 1997-06-03 | Dr. Wolman Gmbh | Wood preservatives |
| US5200421A (en)* | 1991-04-23 | 1993-04-06 | Bayer Aktiengesellschaft | Microbicidal active compound combinations |
| US5527384A (en)* | 1991-08-01 | 1996-06-18 | Hickson International, Plc | Preservatives for wood and other cellulosic materials |
| US5916356A (en)* | 1991-08-01 | 1999-06-29 | Hickson International Plc | Preservatives for wood and other cellulosic materials |
| US5527816A (en)* | 1991-08-26 | 1996-06-18 | Rohm And Haas Company | Fungicidal 2-aryl-2-cyano-2-(aryloxyalkyl)ethyl-1,2-4-triazoles |
| US5874456A (en)* | 1992-02-05 | 1999-02-23 | Novartis Ag | Fungicidal compositions |
| US5624916A (en)* | 1992-06-25 | 1997-04-29 | Rohm And Haas Company | Fungicidal 1,2,4-triazoles |
| US5462931A (en)* | 1992-06-25 | 1995-10-31 | Rohm And Haas Company | Fungicidal 2-heterocyclic-2,2-disubstituted-ethyl 1,2,4-triazoles |
| US5484934A (en)* | 1992-12-30 | 1996-01-16 | Nihon Nohyaku Co., Ltd. | Isothiazole derivatives, a process for production thereof and uses thereof |
| US5342438A (en)* | 1993-02-04 | 1994-08-30 | West Michael H | Remedial wood preservative |
| US5438034A (en)* | 1993-06-09 | 1995-08-01 | Lonza, Inc. | Quaternary ammonium carbonate compositions and preparation thereof |
| US5424077A (en)* | 1993-07-13 | 1995-06-13 | Church & Dwight Co., Inc. | Co-micronized bicarbonate salt compositions |
| US5990043A (en)* | 1993-12-21 | 1999-11-23 | Bayer Aktiengesellschaft | Anti-fouling compositions |
| US5667795A (en)* | 1994-02-07 | 1997-09-16 | Isk Biosciences Corporation | Pesticidal micronutrient compositions containing zinc oxide |
| US5462589A (en)* | 1994-02-22 | 1995-10-31 | Mississippi Forest Products Laboratory | Synergistic wood preservative compositions |
| US5536305A (en)* | 1994-06-08 | 1996-07-16 | Yu; Bing | Low leaching compositions for wood |
| US5714507A (en)* | 1994-07-01 | 1998-02-03 | Janssen Pharmaceutica, N.V. | Synergistic compositions containing metconazole and another triazole |
| US5763364A (en)* | 1994-09-21 | 1998-06-09 | Hoechst Schering Agrevo Gmbh | Thixotropic aqueous plant protection agent suspensions |
| US5426121A (en)* | 1994-10-04 | 1995-06-20 | Akzo Nobel N.V. | Wood preservation formulation comprising complex of a copper cation and alkoxylated diamine |
| US5527423A (en)* | 1994-10-06 | 1996-06-18 | Cabot Corporation | Chemical mechanical polishing slurry for metal layers |
| US5874025A (en)* | 1995-04-12 | 1999-02-23 | Bayer Aktiengesellschaft | Timber preservative containing a copper compound |
| US5879025A (en)* | 1996-08-08 | 1999-03-09 | Trw Vehicle Safety Systems Inc. | Inflator for an inflatable vehicle occupant protection device |
| US5833741A (en)* | 1997-01-16 | 1998-11-10 | Lonza Inc. | Waterproofing and preservative compositons for wood |
| US5874476A (en)* | 1997-07-14 | 1999-02-23 | Rohm And Haas Company | Dihaloformaldoxime carbamates as antimicrobial agents |
| US5972266A (en)* | 1998-02-26 | 1999-10-26 | Trus Joist Macmillan A Limited Partnership | Composite products |
| US6521288B2 (en)* | 2000-05-31 | 2003-02-18 | Board Of Control Of Michigan Technological University | Compositions and methods for wood preservation |
| US6753035B2 (en)* | 2000-05-31 | 2004-06-22 | Board Of Control Of Michigan Technological University | Compositions and methods for wood preservation |
| US20050013939A1 (en)* | 2001-06-15 | 2005-01-20 | Peter Vinden | Boron-based wood preservatives and treatment of wood with boron-based preservatives |
| US6905532B2 (en)* | 2002-02-14 | 2005-06-14 | Phibro-Tech, Inc. | Process for the dissolution of copper metal |
| US20050130866A1 (en)* | 2002-02-14 | 2005-06-16 | Richardson Hugh W. | Process for the dissolution of copper metal |
| US6905531B2 (en)* | 2002-02-14 | 2005-06-14 | Phibro Tech, Inc. | Process for the dissolution of copper metal |
| US20050182152A1 (en)* | 2002-06-06 | 2005-08-18 | Ralph Nonninger | Antimicrobial polymeric coating composition |
| US6843837B2 (en)* | 2002-07-26 | 2005-01-18 | Osmose, Inc. | Polymeric wood preservative compositions |
| US20060076686A1 (en)* | 2003-02-26 | 2006-04-13 | Tuominen Risto | Method for manufacturing an electronic module, and an electronic module |
| US20040176477A1 (en)* | 2003-03-06 | 2004-09-09 | The Procter & Gamble Company | Chitosan powder |
| US20070193473A1 (en)* | 2003-04-09 | 2007-08-23 | Jun Zhang | Micronized wood presservative formulations |
| US20040258767A1 (en)* | 2003-04-09 | 2004-12-23 | Leach Robert M. | Micronized wood preservative formulations |
| US20090092683A1 (en)* | 2003-04-09 | 2009-04-09 | Leach Robert M | Micronized Wood Preservative Formulations |
| US20090035564A1 (en)* | 2003-04-09 | 2009-02-05 | Leach Robert M | Micronized Wood Preservative Formulations |
| US20090028917A1 (en)* | 2003-04-09 | 2009-01-29 | Leach Robert M | Micronized Wood Preservative Formulations |
| US20080286380A1 (en)* | 2003-04-09 | 2008-11-20 | Jun Zhang | Micronized wood preservative formulations |
| US20080260841A1 (en)* | 2003-04-09 | 2008-10-23 | Leach Robert M | Micronized wood preservative formulations |
| US20080210121A1 (en)* | 2003-04-09 | 2008-09-04 | Jun Zhang | Micronized wood preservative formulations |
| US20040258838A1 (en)* | 2003-06-17 | 2004-12-23 | Richardson H. Wayne | Method for preserving wood materials using precipitated copper compounds |
| US20040258768A1 (en)* | 2003-06-17 | 2004-12-23 | Richardson H. Wayne | Particulate wood preservative and method for producing same |
| US20050107467A1 (en)* | 2003-10-17 | 2005-05-19 | Richardson H. W. | Methods for producing and using a Cu(I)-based wood preservative |
| US20050255251A1 (en)* | 2004-05-17 | 2005-11-17 | Hodge Robert L | Composition, method of making, and treatment of wood with an injectable wood preservative slurry having biocidal particles |
| US20060062926A1 (en)* | 2004-05-17 | 2006-03-23 | Richardson H W | Use of sub-micron copper salt particles in wood preservation |
| US20050252408A1 (en)* | 2004-05-17 | 2005-11-17 | Richardson H W | Particulate wood preservative and method for producing same |
| US20050256026A1 (en)* | 2004-05-17 | 2005-11-17 | Hodge Robert L | Compatibilizing surfactant useful with slurries of copper particles |
| US20060086841A1 (en)* | 2004-10-08 | 2006-04-27 | Richardson H W | Milled submicron organic biocides with narrow particle size distribution, and uses thereof |
| US20060075921A1 (en)* | 2004-10-08 | 2006-04-13 | Richardson Hugh W | Milled submicron chlorothalonil with narrow particle size distribution, and uses thereof |
| US20060075923A1 (en)* | 2004-10-12 | 2006-04-13 | Richardson H W | Method of manufacture and treatment of wood with injectable particulate iron oxide |
| US20080199535A1 (en)* | 2004-12-09 | 2008-08-21 | The Dial Corporation | Compositions Having a High Antiviral and Antibacterial Efficacy |
Cited By (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| US8778407B2 (en) | 2003-04-09 | 2014-07-15 | Osmose, Inc. | Micronized wood preservative formulations |
| US8747908B2 (en) | 2003-04-09 | 2014-06-10 | Osmose, Inc. | Micronized wood preservative formulations |
| US8747909B2 (en) | 2003-04-09 | 2014-06-10 | Osmose, Inc. | Micronized wood preservative formulations |
| US20080210121A1 (en)* | 2003-04-09 | 2008-09-04 | Jun Zhang | Micronized wood preservative formulations |
| US8637089B2 (en) | 2003-04-09 | 2014-01-28 | Osmose, Inc. | Micronized wood preservative formulations |
| US20080286380A1 (en)* | 2003-04-09 | 2008-11-20 | Jun Zhang | Micronized wood preservative formulations |
| US8460759B2 (en) | 2003-04-09 | 2013-06-11 | Osmose, Inc. | Micronized wood preservative formulations |
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| US8871277B2 (en) | 2003-06-17 | 2014-10-28 | Osmose, Inc. | Particulate wood preservative and method for producing the same |
| US20070131136A1 (en)* | 2004-04-27 | 2007-06-14 | Osmose, Inc. | Composition And Process For Coloring Wood |
| US9266251B2 (en) | 2004-05-13 | 2016-02-23 | Koppers Performance Chemicals Inc. | Compositions and methods for treating cellulose-based materials with micronized additives |
| US9937634B2 (en) | 2004-05-13 | 2018-04-10 | Koppers Performance Chemicals Inc. | Compositions and methods for treating cellulose-based materials with micronized additives |
| US8603576B2 (en) | 2004-05-13 | 2013-12-10 | Osmose, Inc. | Compositions and methods for treating cellulose based materials with micronized additives |
| US20100119818A1 (en)* | 2004-05-13 | 2010-05-13 | Leach Robert M | Compositions and methods for treating cellulose-based materials with micronized additives |
| US8974854B2 (en) | 2004-05-13 | 2015-03-10 | Koppers Performance Chemicals Inc. | Compositions and methods for treating cellulose-based materials with micronized additives |
| US9314030B2 (en) | 2004-05-17 | 2016-04-19 | Koppers Performance Chemicals Inc. | Particulate wood preservative and method for producing same |
| US20050255251A1 (en)* | 2004-05-17 | 2005-11-17 | Hodge Robert L | Composition, method of making, and treatment of wood with an injectable wood preservative slurry having biocidal particles |
| US20090223408A1 (en)* | 2004-05-17 | 2009-09-10 | Phibrowood, Llc | Use of Sub-Micron Copper Salt Particles in Wood Preservation |
| US8722198B2 (en) | 2004-05-17 | 2014-05-13 | Osmose, Inc. | Method of preserving wood by injecting particulate wood preservative slurry |
| US8158208B2 (en) | 2004-05-17 | 2012-04-17 | Osmose, Inc. | Method of preserving wood by injecting particulate wood preservative slurry |
| US20080213608A1 (en)* | 2004-10-08 | 2008-09-04 | Richardson Hugh W | Milled Submicron Chlorothalonil With Narrow Particle Size Distribution, and Uses Thereof |
| US20060075923A1 (en)* | 2004-10-12 | 2006-04-13 | Richardson H W | Method of manufacture and treatment of wood with injectable particulate iron oxide |
| US9775350B2 (en) | 2004-10-14 | 2017-10-03 | Koppers Performance Chemicals Inc. | Micronized wood preservative formulations in organic carriers |
| US20100068545A1 (en)* | 2005-07-21 | 2010-03-18 | Jun Zhang | Compositions and methods for wood preservation |
| US20070021385A1 (en)* | 2005-07-21 | 2007-01-25 | Jun Zhang | Compositions and methods for wood preservation |
| US8828485B2 (en)* | 2006-02-10 | 2014-09-09 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Carbon-encased metal nanoparticles and sponges as wood/plant preservatives or strengthening fillers |
| US20120021222A1 (en)* | 2006-02-10 | 2012-01-26 | Kun Lian | Carbon-Encased Metal Nanoparticles and Sponges, Methods of Synthesis, and Methods of Use |
| US9574136B2 (en) | 2006-02-10 | 2017-02-21 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Nanoparticles, nanosponges, methods of synthesis, and methods of use |
| US20070259016A1 (en)* | 2006-05-05 | 2007-11-08 | Hodge Robert L | Method of treating crops with submicron chlorothalonil |
| US7666254B1 (en)* | 2006-08-18 | 2010-02-23 | Osmose, Inc. | Borate compositions for wood preservation |
| US8168231B2 (en) | 2006-11-22 | 2012-05-01 | Rohm And Haas Company | Antimicrobial composition useful for preserving wood |
| US20080118575A1 (en)* | 2006-11-22 | 2008-05-22 | John William Ashmore | Antimicrobial composition useful for preserving wood |
| US20080175913A1 (en)* | 2007-01-09 | 2008-07-24 | Jun Zhang | Wood preservative compositions comprising isothiazolone-pyrethroids |
| US20110091575A1 (en)* | 2007-12-13 | 2011-04-21 | Hayson Kimberly S | Strategies for reducing leaching of water-soluble metal biocides from treated wood products |
| US20090162410A1 (en)* | 2007-12-21 | 2009-06-25 | Jun Zhang | Process for preparing fine particle dispersion for wood preservation |
| US20090258943A1 (en)* | 2008-03-14 | 2009-10-15 | Keen Brian T | Hybrid strategies for reducing leaching of metal biocides from biodegradable substrates |
| US8846205B2 (en) | 2008-03-14 | 2014-09-30 | Union Carbide Chemicals & Plastics Technology Llc | Hybrid strategies for reducing leaching of metal biocides from biodegradable substrates |
| US20100016426A1 (en)* | 2008-07-17 | 2010-01-21 | Hayson Kimberly S | Post-impregnation treatments to improve distribution of metal biocides in an impregnated substrate |
| US8105635B2 (en) | 2008-07-17 | 2012-01-31 | Union Carbide Chemicals & Plastics Technology Llc | Post-impregnation treatments to improve distribution of metal biocides in an impregnated substrate |
| US8927063B2 (en) | 2008-12-12 | 2015-01-06 | Timtechchem International Limited | Compositions for the treatment of timber and other wood substrates |
| AU2009337187B2 (en)* | 2008-12-12 | 2014-10-23 | Azelis New Zealand Limited | Compositions for the treatment of timber and other wood substrates |
| WO2010082840A1 (en)* | 2008-12-12 | 2010-07-22 | Tim Tech Chemicals Limited | Compositions for the treatment of timber and other wood substrates |
| US8695707B2 (en) | 2009-06-16 | 2014-04-15 | Schlumberger Technology Corporation | Asphaltene removal composition and methods |
| US20100314117A1 (en)* | 2009-06-16 | 2010-12-16 | Jack Li | Asphaltene removal composition and methods |
| GB2481526B (en)* | 2010-06-21 | 2018-02-14 | Arch Timber Prot Limited | Wood preservative compositions useful for treating copper-tolerant fungi |
| US9023483B2 (en) | 2010-06-21 | 2015-05-05 | Arch Timber Protection Limited | Wood preservative compositions useful for treating copper-tolerant fungi |
| GB2554623A (en)* | 2010-06-21 | 2018-04-04 | Arch Timber Prot Limited | Wood preservative compositions useful for treating copper-tolerant fungi |
| GB2481526A (en)* | 2010-06-21 | 2011-12-28 | Arch Timber Protection Ltd | Wood preservative compositions useful for treating copper-tolerant fungi |
| GB2554623B (en)* | 2010-06-21 | 2018-06-27 | Arch Timber Prot Limited | Wood preservative compositions useful for treating copper-tolerant fungi |
| US9603358B2 (en) | 2011-11-04 | 2017-03-28 | Arch Timber Protection Limited | Additives for use in wood preservation |
| US9961895B2 (en) | 2011-11-04 | 2018-05-08 | Arch Timber Protection Limited | Additives for use in wood preservation |
| US11312038B2 (en) | 2014-05-02 | 2022-04-26 | Arch Wood Protection, Inc. | Wood preservative composition |
| US20190084182A1 (en)* | 2017-03-24 | 2019-03-21 | Koppers Performance Chemicals Inc. | Solvent-borne wood preservative compositions |
| CN110461151A (en)* | 2017-03-24 | 2019-11-15 | 科佩斯性能化学股份有限公司 | Solvent type wood preservative composition |
| EP3599850A1 (en)* | 2017-03-24 | 2020-02-05 | Koppers Performance Chemicals Inc. | Solvent-borne wood preservative compositions |
| AU2018240308B2 (en)* | 2017-03-24 | 2024-02-01 | Koppers Performance Chemicals Inc. | Solvent-borne wood preservative compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0518154A (en) | 2008-11-04 |
| EP1799776B1 (en) | 2013-01-02 |
| US9775350B2 (en) | 2017-10-03 |
| EP2431430A1 (en) | 2012-03-21 |
| AU2005296077A1 (en) | 2006-04-27 |
| PL2431430T3 (en) | 2017-07-31 |
| HN2005000803A (en) | 2010-08-05 |
| GT200500289A (en) | 2006-05-04 |
| AR053648A1 (en) | 2007-05-16 |
| US20170360042A1 (en) | 2017-12-21 |
| WO2006044218A2 (en) | 2006-04-27 |
| CA2584254A1 (en) | 2006-04-27 |
| US20110250358A1 (en) | 2011-10-13 |
| SI1799776T1 (en) | 2013-05-31 |
| EP1799776A2 (en) | 2007-06-27 |
| EP1799776A4 (en) | 2009-05-06 |
| NZ554680A (en) | 2010-10-29 |
| AU2005296077B2 (en) | 2010-12-23 |
| EP2431430B1 (en) | 2017-02-01 |
| TW200632058A (en) | 2006-09-16 |
| WO2006044218A3 (en) | 2007-12-27 |
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