【発明の詳細な説明】「発明の目的」（産業上の利用分野）本発明は顔料の製造方法に関し、鮮明な色相と高い着色
力、光沢の優れた顔料を製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION OBJECTS OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for producing pigments, and more particularly, to a method for producing pigments with clear hue, high tinting power, and excellent gloss.
（従来の技術）一般に各種コーティング、インキまたはプラスチック組
成物中において鮮明な色相と高い着色力、光沢を発揮す
る実用上有効な顔料は微細な粒子からなっている。(Prior Art) Practically effective pigments that exhibit clear hues, high tinting power, and gloss in various coatings, inks, or plastic compositions generally consist of fine particles.
無機顔料、アゾ系顔料等では、顔料の合成段階で微細な
粒子が作られている。フタロシアニン系、キナクリドン
系、アントラキノン系顔料等では、粗製顔料を顔料化と
呼ばれる、場合によっては結晶転移を含む、粒子の微細
化工程により製造されている。For inorganic pigments, azo pigments, etc., fine particles are created during the pigment synthesis stage. Phthalocyanine-based, quinacridone-based, anthraquinone-based pigments, etc. are produced from crude pigments through a particle refinement process called pigmentation, which may include crystal transition in some cases.
しかしながら、これらの方法ではいずれも顔料粒子の微
細化が不十分なため、各種コーティング、インキまたは
プラスチック組成物を製造する工程で強力な分散が必要
であるが、生産効率上十分な分散は行えず高品位な組成
物は得にくい。However, all of these methods do not sufficiently refine the pigment particles, so strong dispersion is required in the process of manufacturing various coatings, inks, or plastic compositions, but sufficient dispersion cannot be achieved in terms of production efficiency. High-quality compositions are difficult to obtain.
顔料の微細化に関し、顔料を界面活性剤とともに分散し
水性分散体を製造する方法は、捺染工業、原液着色工業
あるいは水性塗料工業において行われている。しかし、
顔料の界面活性剤による水中での分散安定性が弱いため
、高顔料濃度の水性分散体は得られず、生産効率が悪い
だけでなく、顔料粒子の微細化も不十分であり、鮮明性
、着色力、光沢の低い品質しか得られない。また、顔料
に界面活性剤が含まれるため、使用用途が限定される欠
点がある。Regarding the miniaturization of pigments, a method of producing an aqueous dispersion by dispersing the pigment together with a surfactant is practiced in the textile printing industry, the stock coloring industry, or the water-based paint industry. but,
Due to the poor dispersion stability of pigments in water due to surfactants, it is not possible to obtain aqueous dispersions with high pigment concentrations, which not only results in poor production efficiency, but also insufficient refinement of pigment particles, resulting in poor sharpness and poor clarity. Only low tinting strength and low gloss quality can be obtained. Furthermore, since the pigment contains a surfactant, there is a drawback that its usage is limited.
（発明が解決しようとする課題）本発明者等は、上記欠点を解決すべく鋭意研究を重ねた
結果、顔料を水溶性の色素誘導体とともに水中で湿式粉
砕することにより顔料の微細化を行い、塗料、グラビア
インキ、オフセットインキ、プラスチックあるいは原液
着色組成物を製造する場合、弱い分散でも鮮明な色相と
高い着色力、光沢の優れた顔料を製造する方法を見出し
、本発明をなすに至った。(Problems to be Solved by the Invention) As a result of extensive research in order to solve the above-mentioned drawbacks, the present inventors micronized the pigment by wet-pulverizing the pigment together with a water-soluble pigment derivative in water. When producing paints, gravure inks, offset inks, plastics, or undiluted coloring compositions, we have discovered a method for producing pigments with a clear hue, high coloring power, and excellent gloss even with weak dispersion, and have achieved the present invention.
「発明の構成」（課題を解決するための手段）本発明は、顔料１００重量部を、水溶性または、塩基あ
るいは酸により水溶性とした色素誘導体１〜２５重量部
とともに、水中で湿式粉砕した後、好ましくは色素誘導
体を不溶化し、単離することからなる顔料の製造方法で
ある。"Structure of the Invention" (Means for Solving the Problems) The present invention involves wet-pulverizing 100 parts by weight of a pigment in water together with 1 to 25 parts by weight of a pigment derivative that is water-soluble or made water-soluble with a base or acid. After that, the pigment derivative is preferably insolubilized and isolated.
本発明において、顔料とは公知の方法で合成されたもの
であり、粗製顔料にも、あるいは、公知の方法により顔
料形態に転化したものにも適用できる。In the present invention, the pigment is one synthesized by a known method, and can be applied to either a crude pigment or one converted into a pigment form by a known method.
顔料は酸化チタン系、酸化鉄系、紺青、カーボンブラン
ク、酸化クロム系、クロム酸鉛系、モリブデン酸鉛系等
の無機顔料、あるいは、フタロシアニン系、アブ系、キ
ナクリドン系、ジケトピロロピロール系、ジオキサジン
系、アントラキノン系、アンスラピリミジン系、アンサ
ンスロン系、インダンスロン系、フラハンスロン系、ピ
ランスロン系、ペリノン系、ペリレン系、チオインジゴ
系等の有機顔料から選ばれる］種である。Pigments include inorganic pigments such as titanium oxide, iron oxide, navy blue, carbon blank, chromium oxide, lead chromate, and lead molybdate, or phthalocyanine, ab-based, quinacridone, diketopyrrolopyrrole, The species is selected from organic pigments such as dioxazine, anthraquinone, anthrapyrimidine, anthanthrone, indanthrone, frahanthrone, pyranthrone, perinone, perylene, and thioindigo.
水溶性または塩基により水溶性となる色素誘導体は、一
般弐Ｐ−Ｘｉ〔Ｉ〕で示される、〔式中、Ｐは有機色素
残基、Ｘは以下に示す置換基、ｉは１〜４の整数を示す
。A dye derivative that is water-soluble or becomes water-soluble by a base is generally represented by 2P-Xi[I], [wherein P is an organic dye residue, X is a substituent shown below, and i is 1 to 4]. Indicates an integer.
Ｃ００Ｍ。C00M.
ＳＯ，Ｍ。SO, M.
Ａ−ＮＲ’ （ＣＨｚ ＣＨＲ２−０−）ｍ Ｈ
）ｎ（式中、Ｍは水素原子またはアルカリ金属、Ｙは水
素原子、−Ｎｏ□、−ＮＨ，または−３ｏ３Ｈ，Ａは−
ＳＯ□−１−ＣＯ−１−ＣＨ２−１または一〇Ｈｔ Ｎ
ＨＣＯＣＨｚ−１Ｒ１は水素原子、アルキル基、また
は（ＣＨｚ ＣＨＲ２０）ｑ、Ｒ２は水素原子またはメ
チル基、ｊは１〜４の整数、ｎは１〜３の整数、ｍとｑ
はそれぞれ２〜１００の整数を示す。）〕から選ばれる少なくとも一種である。A-NR' (CHz CHR2-0-)m H
) n (where M is a hydrogen atom or an alkali metal, Y is a hydrogen atom, -No□, -NH, or -3o3H, A is -
SO□-1-CO-1-CH2-1 or 10HtN
HCOCHz-1R1 is a hydrogen atom, an alkyl group, or (CHz CHR20)q, R2 is a hydrogen atom or a methyl group, j is an integer of 1 to 4, n is an integer of 1 to 3, m and q
each represents an integer from 2 to 100. )] is at least one type selected from
酸により水溶性となる色素誘導体は、一般式〔■〕また
は（ｎ［）で示される、〔（式中、Ｐは有機色素残基、Ａは一８Ｏ□−１Ｃ〇−
２（ＣＨ２） ｍＣＨｚ Ｎ ＨＣＯＣＨｔＳＯｚ Ｎ
Ｈ（ＣＨ２）ｎ−−（ＣＨ２）ｌＩＮＨ（ＣＨ２）ｎ−
１またはｍＣＨ２Ｎ ＨＣＯＣＨｚ Ｎ Ｈ（ＣＨ２）
□−、Ｒ３、Ｒ４はそれぞれ独立に水素原子、炭素数１
〜４のアルキル基、またはＲ３とＲ４とでヘテロ環を形
成したもの、Ｘはハロゲン原子または（Ｒ６ＳＯ４，）
−１Ｒ６は炭素数１〜４のアルキル基、ｋは１〜４の整
数、ｍ、ｎは１〜８の整数を示す。）〕０ （ＣＨ２）、−１ＣＲ２Ｎ ＨＣＯＣＨ
ｚＲ３、Ｒ４はそれぞれ独立に水素原子、炭素数１〜４
のアルキル基、またはＲ３とＲ４とでヘテロ環を形成し
たもの、Ｘはハロゲン原子または（Ｒ’ Ｓ。A dye derivative that becomes water-soluble by an acid is represented by the general formula [■] or (n[), [(wherein P is an organic dye residue and A is 18O□-1C〇-
2 (CH2) mCHz N HCOCHtSOz N
H(CH2)n--(CH2)lINH(CH2)n-
1 or mCH2N HCOCHz NH(CH2)
□-, R3, R4 are each independently a hydrogen atom, carbon number 1
~4 alkyl group, or a heterocycle formed by R3 and R4, X is a halogen atom or (R6SO4,)
-1R6 represents an alkyl group having 1 to 4 carbon atoms, k represents an integer of 1 to 4, and m and n represent integers of 1 to 8. )] 0 (CH2), -1CR2N HCOCH
zR3 and R4 are each independently a hydrogen atom, carbon number 1-4
or a heterocycle formed by R3 and R4, X is a halogen atom or (R'S.
４、）−、Ｒ６は炭素数１〜４のアルキル基、ｋは１〜
４の整数、ｍは１〜８の整数を示す。）から選ばれる少
なくとも一種である。4,)-, R6 is an alkyl group having 1 to 4 carbon atoms, and k is 1 to 4.
An integer of 4, m represents an integer of 1 to 8. ) is at least one type selected from
一酸は塩酸、硫酸等の無機酸または酢酸、プロピオン酸等
の有機脂肪酸、あるいは硫酸エステルから選ばれる少な
くとも一種である。The monoacid is at least one selected from inorganic acids such as hydrochloric acid and sulfuric acid, organic fatty acids such as acetic acid and propionic acid, and sulfuric esters.
色素残基は顔料と類似の構造を持つものが好まＱい。無
機顔料には、白色顔料の場合アントラキノン系、黒色顔
料の場合フタロシアニン系、他はアントラキノン系また
は色相の近いものが好ましい。The dye residue preferably has a structure similar to that of the pigment. The inorganic pigments are preferably anthraquinone-based for white pigments, phthalocyanine-based for black pigments, and anthraquinone-based for others or those having similar hues.
水溶性の色素誘導体の添加量は、顔料１００重量部に対
して１〜２５重量部であり、好ましくは、２〜２０重量
部である。１重量部未満では水性分散体の粘度が高（な
り、粉砕効果が低下する。また、２５重量部を超えると
、色相が母体となる顔料と異なるだけでなく、顔料の着
色力や耐候性等の品質が劣化する。The amount of the water-soluble pigment derivative added is 1 to 25 parts by weight, preferably 2 to 20 parts by weight, per 100 parts by weight of the pigment. If it is less than 1 part by weight, the viscosity of the aqueous dispersion will be high (and the crushing effect will be reduced).If it exceeds 25 parts by weight, not only will the hue be different from that of the base pigment, but also the coloring power and weather resistance of the pigment will be affected. quality deteriorates.
湿式粉砕における水性分散体中の顔料濃度は、５〜５０
重量％、好ましくは１０〜４０重量％である。The pigment concentration in the aqueous dispersion in wet grinding is 5 to 50
% by weight, preferably 10-40% by weight.
５重量％未満では生産効率が悪く、５０重量％を超える
と水性分散体の粘度が高くなり、粉砕効果が低下する。If it is less than 5% by weight, production efficiency will be poor, and if it exceeds 50% by weight, the viscosity of the aqueous dispersion will increase and the pulverizing effect will decrease.
本発明の色素誘導体は、水中での湿式粉砕による顔料の
分散工程において、水性分散体中の顔料濃度を上記範囲
に高めても粘度上昇を起こさず、分散効率と生産効率を
高める効果がある。これは、水溶性の色素誘導体の持つ
アンカー効果と電気的効果により水性分散体の安定性が
、界面活性剤に比べ著しく高められているためである。The pigment derivative of the present invention does not cause an increase in viscosity even if the pigment concentration in the aqueous dispersion is increased to the above range in the pigment dispersion process by wet grinding in water, and has the effect of increasing dispersion efficiency and production efficiency. This is because the stability of the aqueous dispersion is significantly improved compared to surfactants due to the anchor effect and electrical effect of the water-soluble dye derivative.
湿式粉砕は、例えば、ボールミル、アトライターサンド
ミル、ビーズミル、アトマイザ−その他の粉砕機で行い
、水性分散体の粒度が、遠心沈降型粒度分布計において
、粗大粒子１０μｍ以下、メデイアン径１μｍ以下、好
ましくは粗大粒子５μｍ以下、メデイアン径０．５μｍ
以下となるまで粉砕する。Wet pulverization is performed using a pulverizer such as a ball mill, attritor sand mill, bead mill, atomizer, etc., and the particle size of the aqueous dispersion is determined to be 10 μm or less for coarse particles and 1 μm or less for the median diameter, preferably 1 μm or less in a centrifugal sedimentation type particle size distribution analyzer. Coarse particles 5μm or less, median diameter 0.5μm
Grind until the following.
水溶性の色素誘導体の不溶化は、染料状態の色素誘導体
を顔料状態にするため行う処理で、水または塩基により
水溶性となる色素誘導体の場合は、アミン系界面活性剤
または２価以上の金属より選ばれる少なくとも１種以上
で行われ、酸により水溶性となる色素誘導体の場合は、
ロジンまたは変性ロジンのアルカリ塩もしくは、水酸化
ナトリウム、炭酸ナトリウム等の無機の塩基より選ばれ
る少なくとも１種以上で行われる。Insolubilization of water-soluble pigment derivatives is a process performed to convert the pigment derivatives in the dye state into the pigment state. In the case of pigment derivatives that become water-soluble with water or a base, it is necessary to In the case of dye derivatives that are made with at least one selected species and become water-soluble with acid,
This is carried out using at least one selected from alkali salts of rosin or modified rosin, and inorganic bases such as sodium hydroxide and sodium carbonate.
アミン系界面活性剤は一般に良く知られているものであ
り、例えば、アルキルアミン、ジメチルアルキルアミン
、アルキルトリメチルアンモニウムクロリド、アルキル
トリエチルアンモニウムクロリド、ジアルキルジメチル
アンモニウムクロリド、アルキルプロピレンジアミン、
アルキルアミンアセテート、ジアルキルアミンアセテー
ト、トリエチルテトラアミン等があげられる。Amine surfactants are generally well known, and include, for example, alkylamines, dimethylalkylamines, alkyltrimethylammonium chlorides, alkyltriethylammonium chlorides, dialkyldimethylammonium chlorides, alkylpropylene diamines,
Examples include alkylamine acetate, dialkylamine acetate, triethyltetraamine, and the like.
さらに、該界面活性剤の種類をあげると、下記で表され
る構造をとる単独または混合物でる。Further, the surfactants can be used singly or as a mixture having the structure shown below.
Ｒ’ ＮＨ２、Ｒ’ −ＮＨ−Ｒ” Ｃ０ＯＨまたはＲ’ ＮＨ（ＣＨ２）。ＮＨ−Ｒ２ＣＯＯＨ（Ｒ’
は不飽和を含む長鎖アルキル基であり０６〜Ｃ２゜の間
である。Ｒ２−Ｒ４はＨまたは不飽和を含むアルキル基
でありＣ１〜Ｃ２□の間である。Ｘは陰イオンで主にハ
ロゲン原子であり、ｎは１〜２２までの整数である。）
。R' NH2, R'-NH-R" C0OH or R' NH(CH2). NH-R2COOH(R'
is a long chain alkyl group containing unsaturation and is between 06 and C2°. R2-R4 are H or an alkyl group containing unsaturation, and are between C1 and C2□. X is an anion, mainly a halogen atom, and n is an integer from 1 to 22. )
.
２価以上の金属は、アルカリ土類金属、遷移元素でＣａ
、Ｂａ、Ｓｒ、ＡＩ、Ｍｎ等があげられる。Divalent or higher-valent metals include alkaline earth metals, transition elements such as Ca
, Ba, Sr, AI, Mn, etc.
不溶化剤の添加量は、水溶性の色素誘導体に対し０．８
〜５倍当量、好ましくは１〜３倍当量である。The amount of insolubilizing agent added is 0.8 to the water-soluble dye derivative.
~5 times equivalent, preferably 1 to 3 times equivalent.
０．８倍当量未満では色素誘導体の不溶化が不十分でブ
リードの原因となる。また５倍当量を超えると、鮮明性
、着色力、光沢等の品質が低下する。If the amount is less than 0.8 times equivalent, the dye derivative is insufficiently insolubilized and causes bleeding. Moreover, when the amount exceeds 5 times the equivalent, qualities such as sharpness, coloring power, and gloss deteriorate.
水溶性の色素誘導体を不溶化した後の水性分散体は、常
法により濾過、水洗を行い顔料を単離する。After insolubilizing the water-soluble pigment derivative, the aqueous dispersion is filtered and washed with water in a conventional manner to isolate the pigment.
顔料はこのまま湿潤状態で使用することも、乾燥により
粉末状態で使用することも可能である。The pigment can be used as it is in a wet state, or it can be dried and used in a powdered state.
乾燥方法は、通常の箱型乾燥機を用いても、スプレー燥
機を用いても良いが、本発明の箱型乾燥機による乾燥顔
料は、特に、グラビアインキ用途で、湿式粉砕を行わな
い従来のスプレー乾燥顔料に匹敵する高い光沢が得られ
る効果がある。As for the drying method, a normal box-type dryer or a spray dryer may be used, but the pigment dried by the box-type dryer of the present invention is particularly suitable for use in gravure ink than conventional methods that do not involve wet pulverization. It has the effect of providing high gloss comparable to spray-dried pigments.
以下実施例により本発明を説明するが、本発明は実施例
により規制されるものではない。例中、部とは重量部を
、％とは重量％をそれぞれ表わす。The present invention will be explained below with reference to Examples, but the present invention is not limited by the Examples. In the examples, "part" means part by weight, and "%" means % by weight.
実施例１水２７部およびβ型銅フタロシアニンブルー顔料の顔料
濃度３０％のウェットケーキ３３３部に、下記に示す銅
フタロシアニン誘導体１０部をサンドミルを配合し湿式
粉砕した後、塩化カルシウムを、銅フタロシアニン誘導
体に対しＣａが１．５倍当量になるよう添加し混合、攪
拌を行った。常法により濾過、水洗、乾燥し、１０８部
の顔料を得た。Example 1 10 parts of the copper phthalocyanine derivative shown below was added to 27 parts of water and 333 parts of a wet cake with a pigment concentration of β-type copper phthalocyanine blue pigment at 30% using a sand mill, and after wet grinding, calcium chloride was mixed with the copper phthalocyanine derivative. Ca was added in an amount of 1.5 times the equivalent amount, and mixed and stirred. The mixture was filtered, washed with water, and dried in a conventional manner to obtain 108 parts of pigment.
この顔料のポリアミド系グラビアインキは着色力１２０
、光沢値８８であった。This pigmented polyamide gravure ink has a coloring power of 120.
, the gloss value was 88.
ＣｕＰｃ−３ｏ３Ｎａ（ＣｕＰｃは銅フタロシアニン残基を示す。）比較例１
−１実施例１において、銅フタロシアニン誘導体をト′デシ
ルペンゼンスルホン酸ソーダ塩に換えた他は同様の操作
を行い９６部の顔料を得た。CuPc-3o3Na (CuPc indicates copper phthalocyanine residue) Comparative example 1
-1 The same procedure as in Example 1 was carried out except that the copper phthalocyanine derivative was replaced with to'decylpenzene sulfonic acid sodium salt to obtain 96 parts of a pigment.
この顔料のポリアミド系グラビアインキは着色力１００
、光沢値６９であった。This pigmented polyamide gravure ink has a coloring power of 100.
, the gloss value was 69.
比較例１−２実施例１において、銅フタロシアニン誘導体を未添加と
した他は同様の湿式粉砕を行ったが、水性スラリーの粘
度が高く、分散できなかった。Comparative Example 1-2 The same wet pulverization as in Example 1 was performed except that the copper phthalocyanine derivative was not added, but the aqueous slurry had a high viscosity and could not be dispersed.
実施例２〜６実施例１に準じ、表１に示す顔料、色素誘導体、及び不
溶化剤を用い顔料を得た。Examples 2 to 6 Pigments were obtained according to Example 1 using the pigments, dye derivatives, and insolubilizers shown in Table 1.
比較例２〜６比較例１−１に準じ、表１に示す顔料、界面活性剤、及
び不溶化剤を用い顔料を得た。なお、比較例番号はそれ
ぞれ実施例番号に対応する。Comparative Examples 2 to 6 Pigments were obtained according to Comparative Example 1-1 using the pigments, surfactants, and insolubilizers shown in Table 1. Note that the comparative example numbers correspond to the example numbers, respectively.
（評価方法）グラビアインキ試験二顔料１０部とグラビアインキフェ
ス９０部をペイントコンディショナーで分散した。得ら
れたインキを、ポリアミド系の場合はトリアセテートフ
ィルムに、ライムロジン系の場合はコート紙に展色した
。着色力の比較は白インキカットで行った。(Evaluation method) 10 parts of gravure ink test 2 pigment and 90 parts of gravure ink face were dispersed with a paint conditioner. The obtained ink was spread on a triacetate film in the case of a polyamide-based ink, and on coated paper in the case of a lime rosin-based ink. Comparison of coloring strength was performed using white ink cut.
オフセットインキ試験：顔料１０部とロジン変性フェノ
ール樹脂系オフセソトインキフェス９０部を３本ロール
で分散した。得られたインキをコート紙に展色した。着
色力の比較は白インキカットで行った。Offset ink test: 10 parts of pigment and 90 parts of rosin-modified phenolic resin offset ink face were dispersed using three rolls. The obtained ink was spread on coated paper. Comparison of coloring strength was performed using white ink cut.
塗料試験：顔料６部とアミノアルキド樹脂系焼付塗料ワ
ニス９４部をペイントコンディショナーで分散した。得
られたエナメルをコート紙に展色し、焼付を行った。着
色力の比較は白エナメルカッ１−で行った。Paint test: 6 parts of pigment and 94 parts of amino alkyd resin baking paint varnish were dispersed with paint conditioner. The obtained enamel was spread on coated paper and baked. Comparison of tinting strength was carried out using white enamel cup 1-.
着色力は、白カットした展色物をカラーマシンで測定し
Ｌ”を求め、同一番号の比較例を基準とし実施例の着色
力を求めた。The coloring power was determined by measuring L'' of a white-cut colored product using a color machine, and the coloring power of the example was determined using a comparative example with the same number as a standard.
光沢は、濃色の展色物を光沢針で測定し、６０度光沢を
求めた。The gloss was measured by measuring the dark color spread with a gloss needle to determine the 60 degree gloss.
（以下余白）トン残基、■はジオキサジンバイオレット残基を示す。(Margin below)ton residue, ■ indicates dioxazine violet residue.
）実施例７水１２部およびβ型銅フタロシアニンブルー顔料の顔料
濃度３０％のウェットケーキ３３３部に、下記に示す銅
フタロシアニン誘導体５部を酢酸で水溶化し、サンドミ
ルを用い湿式粉砕した後、ロジンナトリウム塩を銅フタ
ロシアニン誘導体に対しロジンが１．５倍当量になるよ
う添加し混合、攪拌を行った。常法により濾過、水洗、
乾燥し、１０１部の顔料を得た。) Example 7 To 12 parts of water and 333 parts of a wet cake with a pigment concentration of β-type copper phthalocyanine blue pigment of 30%, 5 parts of the copper phthalocyanine derivative shown below was made water-solubilized with acetic acid, and after wet grinding using a sand mill, rosin sodium was added. Salt was added in an amount of 1.5 times the equivalent of rosin to the copper phthalocyanine derivative, and the mixture was mixed and stirred. Filter, wash with water, and
It was dried to obtain 101 parts of pigment.
この顔料のライムロジン系グラビアインキは着色力１２
３、光沢値８０であった。This pigmented lime rosin gravure ink has a coloring power of 12
3. The gloss value was 80.
ＣｕＰｃ−３Ｏ２ＮＨ（ＣＨｚ ）＋Ｎ（Ｃ３Ｈｑ ）
ｚ（ＣｕＰｃは銅フタロシアニン残基を示す。）比較例
７実施例７において、銅フタロシアニン誘導体をジステア
リルジメチルアンモニウムクロリドに換えた他は同様の
操作を行い、９３部の顔料を得た。CuPc-3O2NH(CHz)+N(C3Hq)
z (CuPc indicates a copper phthalocyanine residue.) Comparative Example 7 The same operation as in Example 7 was performed except that the copper phthalocyanine derivative was replaced with distearyldimethylammonium chloride, to obtain 93 parts of a pigment.
この顔料のライムロジン系グラビアインキは着色力１０
０、光沢値６７であった。This pigmented lime rosin gravure ink has a coloring power of 10.
0, and the gloss value was 67.
表 １（ＣｕＰｃば銅フタロシアニン残基、Ｑはキナクリ実施
例８〜１１実施例７に準じ、表２に示す顔料及び色素誘導体を用い
顔料を得た。Table 1 (CuPc is copper phthalocyanine residue, Q is quinacrylate) Examples 8 to 11 According to Example 7, pigments were obtained using the pigments and dye derivatives shown in Table 2.
比較例８〜１１比較例７に準じ、表２に示す顔料及び界面活性剤を用い
顔料を得た。なお、比較例番号はそれぞれ実施例番号に
対応する。Comparative Examples 8 to 11 According to Comparative Example 7, pigments were obtained using the pigments and surfactants shown in Table 2. Note that the comparative example numbers correspond to the example numbers, respectively.
（以下余白）表（ＣｕＰｃば銅フタロシアニン残基、Ｑはキナクリドン
残基を示す。）実施例１２水１２部およびβ型銅フタロシアニンブルー顔料実施例
１において、β型銅フタロシアニンブルー顔料をβ型銅
フタロシアニンブルー粗製顔料に換えた他は同様の操作
を行い、１０７部の顔料を得た。(Space below) Table (CuPc indicates copper phthalocyanine residue, Q indicates quinacridone residue.) Example 12 12 parts of water and β-type copper phthalocyanine blue pigment In Example 1, β-type copper phthalocyanine blue pigment was replaced with β-type copper phthalocyanine blue pigment. The same operation was carried out except that the crude phthalocyanine blue pigment was used to obtain 107 parts of pigment.
この顔料のポリアミド系グラビアインキは着色力１２５
、光沢値７９であった。This pigmented polyamide gravure ink has a coloring power of 125.
, the gloss value was 79.
比較例１２実施例１４において、銅フタロシアニン誘導体をドデシ
ルベンゼンスルホン酸ソーダ塩に換えた他は同様の操作
を行い９４部の顔料を得た。Comparative Example 12 The same procedure as in Example 14 was carried out except that the copper phthalocyanine derivative was replaced with dodecylbenzenesulfonic acid sodium salt to obtain 94 parts of pigment.
この顔料のポリアミド系グラビアインキは着色力１００
、光沢値５８であった。This pigmented polyamide gravure ink has a coloring power of 100.
, the gloss value was 58.
比較例１３実施例１２において、銅フタロシアニン誘導体を未添加
とした他は同様の湿式粉砕を行ったが、水性スラリーの
粘度が高く、分散できなかった。Comparative Example 13 The same wet pulverization as in Example 12 was carried out except that the copper phthalocyanine derivative was not added, but the aqueous slurry had a high viscosity and could not be dispersed.
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63253560AJPH0774312B2 (en) | 1988-10-07 | 1988-10-07 | Pigment manufacturing method |
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63253560AJPH0774312B2 (en) | 1988-10-07 | 1988-10-07 | Pigment manufacturing method |
| Publication Number | Publication Date |
|---|---|
| JPH02102272Atrue JPH02102272A (en) | 1990-04-13 |
| JPH0774312B2 JPH0774312B2 (en) | 1995-08-09 |
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63253560AExpired - Fee RelatedJPH0774312B2 (en) | 1988-10-07 | 1988-10-07 | Pigment manufacturing method |
| Country | Link |
|---|---|
| JP (1) | JPH0774312B2 (en) |
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06228454A (en)* | 1991-03-07 | 1994-08-16 | Toyo Ink Mfg Co Ltd | Production of beta-type dioxazine pigment |
| EP0685530A1 (en) | 1994-05-30 | 1995-12-06 | Nippon Kayaku Kabushiki Kaisha | Process for producing dioxazine compounds, colored materials therewith and dioxazine compounds having a plate-like crystal form |
| JPH0848687A (en)* | 1994-05-30 | 1996-02-20 | Nippon Kayaku Co Ltd | Production of dioxazine compound, coloring material and plate-like crystal |
| WO2009016945A1 (en)* | 2007-07-31 | 2009-02-05 | Dic Corporation | Dioxadine sulfamoyl compound, coloring powder composition for color filter, and color filer |
| WO2011052365A1 (en)* | 2009-10-30 | 2011-05-05 | 花王株式会社 | Aqueous dispersion for inkjet printing |
| WO2016132711A1 (en)* | 2015-02-20 | 2016-08-25 | デクセリアルズ株式会社 | Phthalocyanine-based complex compound |
| JP2018529785A (en)* | 2015-06-25 | 2018-10-11 | クラリアント・プラスティクス・アンド・コーティングス・リミテッド | Naphthol AS pigment mixture |
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06228454A (en)* | 1991-03-07 | 1994-08-16 | Toyo Ink Mfg Co Ltd | Production of beta-type dioxazine pigment |
| EP0685530A1 (en) | 1994-05-30 | 1995-12-06 | Nippon Kayaku Kabushiki Kaisha | Process for producing dioxazine compounds, colored materials therewith and dioxazine compounds having a plate-like crystal form |
| JPH0848687A (en)* | 1994-05-30 | 1996-02-20 | Nippon Kayaku Co Ltd | Production of dioxazine compound, coloring material and plate-like crystal |
| US5734050A (en)* | 1994-05-30 | 1998-03-31 | Nippon Kayaku Kabushiki Kaisha | Process for producing dioxazine compounds, colored materials therewith and dioxazine compounds having a plate-like crystal form |
| US5859242A (en)* | 1994-05-30 | 1999-01-12 | Nippon Kayaku Kabushiki Kaisha | Process for producing dioxazine compounds, colored materials therewith and dioxazine compounds having a plate-like crystal form |
| GB2468561A (en)* | 2007-07-31 | 2010-09-15 | Dainippon Ink & Chemicals | Dioxadine sulfamoyl compound, colouring powder composition for color filter, and color filer |
| WO2009016945A1 (en)* | 2007-07-31 | 2009-02-05 | Dic Corporation | Dioxadine sulfamoyl compound, coloring powder composition for color filter, and color filer |
| GB2468561B (en)* | 2007-07-31 | 2011-11-16 | Dainippon Ink & Chemicals | Colouring powder composition comprising a dioxazine sulfamoyl compound |
| US8068297B2 (en) | 2007-07-31 | 2011-11-29 | Dic Corporation | Dioxazine sulfamoyl compound, coloring powder composition for color filter, and color filter |
| WO2011052365A1 (en)* | 2009-10-30 | 2011-05-05 | 花王株式会社 | Aqueous dispersion for inkjet printing |
| US9133356B2 (en) | 2009-10-30 | 2015-09-15 | Kao Corporation | Aqueous dispersion for inkjet printing |
| WO2016132711A1 (en)* | 2015-02-20 | 2016-08-25 | デクセリアルズ株式会社 | Phthalocyanine-based complex compound |
| CN107207873A (en)* | 2015-02-20 | 2017-09-26 | 迪睿合电子材料有限公司 | Phthalocyanine system complex |
| JP2018529785A (en)* | 2015-06-25 | 2018-10-11 | クラリアント・プラスティクス・アンド・コーティングス・リミテッド | Naphthol AS pigment mixture |
| Publication number | Publication date |
|---|---|
| JPH0774312B2 (en) | 1995-08-09 |
| Publication | Publication Date | Title |
|---|---|---|
| US4464203A (en) | Highly concentrated, dust-free, solid and readily dispersible pigment formulations and their use | |
| US4444592A (en) | Pigment compositions and processes therefor | |
| JP4101356B2 (en) | Pigment composition | |
| EP0485441A1 (en) | New pigment preparations based on perylene compounds. | |
| US20010047740A1 (en) | Pigment compositions, production process thereof, colorants, and colored articles | |
| CA1245807A (en) | Color enhanced permanent pigments from precipitated cationic dyes | |
| JP3337234B2 (en) | New pigment preparations based on dioxazine compounds | |
| MXPA04010752A (en) | Compositions and methods for imparting improved rheology on pigment based inks and paints. | |
| JP2507810B2 (en) | Pigment dispersant, pigment composition, paint and printing ink | |
| JP2000297224A (en) | Pigment preparation containing 2 or more kinds of perylene compounds | |
| JPH02102272A (en) | Pigment manufacturing method | |
| US4709021A (en) | Copper phthalocyanine pigments | |
| JPH0651847B2 (en) | Easy dispersible organic pigment | |
| JPS6259146B2 (en) | ||
| GB1575561A (en) | Pigment composition | |
| JP4645865B2 (en) | Pigment additive, pigment composition and paint resin composition | |
| JPH0252659B2 (en) | ||
| JP3896699B2 (en) | Method for producing aqueous pigment dispersion | |
| JPH02102273A (en) | Method for producing easily dispersible pigment | |
| JPH0619050B2 (en) | Dispersion method of perylene and perinone pigments | |
| JPH06316676A (en) | Aqueous pigment dispersion | |
| JPH03223364A (en) | Copper phthalocyanine pigment composition and pigment dispersion composition using the same | |
| JPH02294363A (en) | Production of azo lake dye | |
| US6653390B1 (en) | Triphenylmethane dyes for water-based compositions | |
| JPH04178471A (en) | Pigment composition and paint composition using the same |
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |