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Polyvinylpyrrolidone

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(Redirected fromPoly-N-vinylpyrrolidine)
Water-soluble polymer

Polyvinylpyrrolidone
150pxc
150pxc
Names
IUPAC name
1-Ethenylpyrrolidin-2-one
Other names
PVP, PNVP, povidone, polyvidone, kollidon
Poly[1-(2-oxo-1-pyrrolidinyl)ethylen]
1-Ethenyl-2-pyrrolidon homopolymer
1-Vinyl-2-pyrrolidinon-polymere
Poly-N-vinylpyrrolidine
Identifiers
3D model (JSmol)
AbbreviationsPVP, NVP, PNVP
ChEMBL
ChemSpider
  • none
ECHA InfoCard100.111.937Edit this at Wikidata
E numberE1201(additional chemicals)
UNII
  • N1(C(CCC1)=O)[C@@H](C*)*
Properties
(C6H9NO)n
Molar mass2,500–2,500,000 g·mol−1
Appearancewhite to light yellow, hygroscopic, amorphous powder
Density1.2 g/cm3
Melting point150 to 180 °C (302 to 356 °F; 423 to 453 K) (glass temperature)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Polyvinylpyrrolidone (PVP), also commonly calledpovidone, is a water-solublepolymer compound made from themonomerN-vinylpyrrolidone.[1] PVP is available in a range of molecular weights and related viscosities, and can be selected according to the desired application properties.[2]

Uses

[edit]

Medical

[edit]
Structure of povidone-iodine complex, a common antiseptic[3]

There are high-purity injectable grades of PVP available on the market, for specific use in intravenous, intramuscular, and subcutaneous applications.[2]

PVP is a frequently usedbinder in pharmaceutical tablet formulations.[4] Pharmacokinetic studies in humans and various laboratory animal models indicate no to very little systemic absorption of PVP following oral administration.[5]

PVP added toiodine forms a complex calledpovidone-iodine that possessesdisinfectant properties.[6] This complex is used in various products such as solutions,ointment,pessaries, liquid soaps, and surgical scrubs. It is sold under the trade names Pyodine and Betadine, among others.

It is used inpleurodesis (fusion of the pleura because of incessant pleural effusions). For this purpose, povidone-iodine is as effective and safe astalc, and may be preferred because of its easy availability and low cost.[7]

PVP is used in somecontact lenses and their packaging solutions. It reduces friction, thus acting as a lubricant, orwetting agent, built into the lens. Examples of this use includeBausch & Lomb's Ultra contact lenses with MoistureSeal Technology,[8] Air Optix contact lens packaging solution (as an ingredient called "copolymer 845"),[9] andJohnson & Johnson'sAcuvue contact lenses.[10]

PVP is used as a lubricant in some eye drops, e.g. Bausch & Lomb's Soothe.[11]

PVP was used as aplasmavolume expander for trauma victims after the 1950s. It is not preferred as a volume expander due to its ability to provoke histamine release and also interfere with blood grouping.[citation needed]

Technical

[edit]

PVP is also used in many technical applications:

Other uses

[edit]

PVP binds topolar molecules exceptionally well, owing to itspolarity. This has led to its application in coatings for photo-quality ink-jet papers and transparencies, as well as in inks forinkjet printers.

PVP is also used in personal care products, such asshampoos andtoothpastes, inpaints, andadhesives that must be moistened, such as old-stylepostage stamps andenvelopes. It has also been used incontact lens solutions and insteel-quenching solutions.[18][19] PVP is the basis of the early formulas forhair sprays andhair gels, and still continues to be a component of some.

As afood additive, PVP is astabilizer and hasE numberE1201.PVPP (crospovidone) isE1202. It is also used in the wine industry as afining agent forwhite wine and somebeers.

In in-vitro fertilisation laboratories, polyvinylpyrrolidone is used to slow down spermatozoa in order to capture them for e.g. ICSI.

Inmolecular biology, PVP can be used as a blocking agent duringSouthern blot analysis as a component ofDenhardt's buffer. It is also exceptionally good at absorbing polyphenols during DNA purification.Polyphenols are common in many plant tissues and can deactivate proteins if not removed and therefore inhibit many downstream reactions like PCR.

Inmicroscopy, PVP is useful for making an aqueous mounting medium.[20]

PVP can be used to screen forphenolic properties, as referenced in a 2000 study on the effect of plant extracts on insulin production.[21]

Safety

[edit]

The U.S.Food and Drug Administration (FDA) has approved this chemical for many uses,[22] and it isgenerally recognized as safe (GRAS). PVP is included in the Inactive Ingredient Database for use in oral, topical, and injectable formulations.

However, there have been documented cases ofallergic reactions to PVP/povidone, particularly regardingsubcutaneous (applied under the skin) use and situations where the PVP has come in contact with autologousserum (internal blood fluids) andmucous membranes.

Examples of documentedallergic reactions:

Additionally, Povidone is commonly used in conjunction with otherchemicals. Some of these, such asiodine andpenicillin,[26] for example, are blamed forallergic responses. Yet subsequent testing results in some patients show no signs ofallergy to the suspectchemical.Allergies attributed to these other chemicals may possibly be caused by the PVP instead.[27][28]

Properties

[edit]

PVP is soluble inwater and other polarsolvents. For example, it is soluble in various alcohols, such asmethanol andethanol,[29] as well as in more exotic solvents like thedeep eutectic solvent formed bycholine chloride andurea (Relin).[30] When dry it is a light flakyhygroscopic powder, readily absorbing up to 40% of its weight in atmospheric water. In solution, it has excellent wetting properties and readily forms films. This makes it good as a coating or an additive to coatings.

A 2014 study found fluorescent properties of PVP and its oxidized hydrolyzate.[31]

History

[edit]

Povidone was first synthesized byBASF chemistWalter Reppe, and a patent was filed in 1939 for one of the derivatives of acetylene chemistry. PVP was initially used as a blood plasma substitute and later in a wide variety of applications in medicine, pharmacy, cosmetics and industrial production.[32][33] BASF continues to make PVP, including a pharmaceutical portfolio under the brand name of Kollidon.[2]

Cross-linked derivatives

[edit]
Main article:Polyvinylpolypyrrolidone

See also

[edit]

References

[edit]
  1. ^Haaf, F.; Sanner, A.; Straub, F. (1985)."Polymers of N-Vinylpyrrolidone: Synthesis, Characterization and Uses".Polymer Journal.17:143–152.doi:10.1295/polymj.17.143.
  2. ^abc"Povidones, Copovidones, and Crospovidones for Pharmaceutical Products".BASF Pharma. Retrieved11 June 2022.
  3. ^Kutscher, Bernhard (2020). "Dermatologicals (D), 4. Antiseptics and Disinfectants (D08), Anti‐Acne Preparations (D10), and Other Dermatological Preparations (D11)".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–22.doi:10.1002/14356007.w08_w03.ISBN 978-3-527-30673-2.
  4. ^Bühler, Volker (2005).Polyvinylpyrrolidone Excipients for Pharmaceuticals: Povidone, Crospovidone and Copovidone. Berlin, Heidelberg, New York: Springer. pp. 1–254.doi:10.1007/b138598.ISBN 978-3540234128.
  5. ^Kurakula M, Rao GS (December 2020)."Pharmaceutical assessment of polyvinylpyrrolidone (PVP): As excipient from conventional to controlled delivery systems with a spotlight on COVID-19 inhibition".Journal of Drug Delivery Science and Technology.60 102046.doi:10.1016/j.jddst.2020.102046.PMC 7462970.PMID 32905026.
  6. ^PVP-Iodine. ispcorp.com. 2004.
  7. ^Das SK, Saha SK, Das A, Halder AK, Banerjee SN, Chakraborty M (2008). "A study of comparison of efficacy and safety of talc and povidone iodine for pleurodesis of malignant pleural effusions".Journal of the Indian Medical Association.106 (9):589–90, 592.PMID 19552086.
  8. ^"Contact Lens Design & Materials: New Lens Technology Targets Improved Vision and Comfort".Contact Lens SPECTRUM. 1 May 2014. Retrieved27 September 2017.
  9. ^"Contact Lens Materials: The Evolution of Contact Lens Wetting Agents".Contact Lens SPECTRUM. 1 October 2009. Retrieved27 September 2017.
  10. ^"Deciphering Contact Lens Terminology".Review of Optometry. 15 August 2022. Retrieved7 November 2024.
  11. ^"Soothe Hydration Lubricant Eye Drops". Bausch & Lomb. Retrieved27 September 2017.
  12. ^Swei, J.; Talbot, J. B. (2006). "Development of high-definition aqueous polyvinylpyrrolidone photoresists for cathode ray tubes".Journal of Applied Polymer Science.102 (2):1637–1644.Bibcode:2006JAPS..102.1637S.doi:10.1002/app.23950.
  13. ^Chen, Tianming "Dental bleach",U.S. patent 6,730,316, Priority date 27 January 2001
  14. ^"Pharmaceutical Povidones, Copovidones, Crospovidones".pharmaceutical.basf.com. Retrieved27 April 2021.
  15. ^Kavakka, J. S.; KilpeläInen, I.; Heikkinen, S. (2009). "General Chromatographic NMR Method in Liquid State for Synthetic Chemistry: Polyvinylpyrrolidone Assisted DOSY Experiments".Organic Letters.11 (6):1349–52.doi:10.1021/ol9001398.PMID 19231850.
  16. ^Koczkur, Kallum M.; Mourdikoudis, Stefanos; Polavarapu, Lakshminarayana; Skrabalak, Sara E. (2015)."Polyvinylpyrrolidone (PVP) in nanoparticle synthesis"(PDF).Dalton Transactions.44 (41):17883–17905.doi:10.1039/C5DT02964C.PMID 26434727.S2CID 9323765.
  17. ^Li, Bo; Zhang, Yanan; Fu, Lin (2018)."Surface passivation engineering strategy to fully-inorganic cubic CsPbI 3 perovskites for high-performance solar cells"(PDF).Nature.9 (1): 8.Bibcode:2018NatCo...9.1076L.doi:10.1038/s41467-018-03169-0.PMC 5852044.PMID 29540764.Archived(PDF) from the original on 30 October 2018.
  18. ^Fischer, Frank & Bauer, Stephan (2009). "Ein Polyvinylpyrrolidon (PVP): ein vielseitiges Spezialpolymer – Verwendung in der Keramik und als Metallabschreckmedium".Keramische Zeitschrift.61 (6):382–385.
  19. ^Göthlich, Alexander; Koltzenburg, Sebastian; Schornick, Gunnar (2005). "Funktionale Polymere im Alltag: Vielseitig".Chemie in unserer Zeit.39 (4):262–273.doi:10.1002/ciuz.200400346.
  20. ^Lillie RD & Fullmer HM (1976)Histopathologic Technic and Practical Histochemistry, 4th ed. New York: McGraw-Hill, p. 411.ISBN 0-07-037862-2.
  21. ^Broadhurst, C. Leigh; Polansky, Marilyn M; Anderson, Richard A (2 March 2000). "Insulin-like Biological Activity of Culinary and Medicinal Plant Aqueous Extracts in Vitro".Journal of Agricultural and Food Chemistry.48 (3):849–52.Bibcode:2000JAFC...48..849B.doi:10.1021/jf9904517.PMID 10725162.
  22. ^Inactive Ingredients in FDA Approved Drugs. FDA/Center for Drug Evaluation and Research, Office of Generic Drugs, Division of Labeling and Program Support. Database Update Frequency: Quarterly. Data Through: 6 January 2010. Database Last Updated: 13 January 2010 – search on povidone for list of approved items
  23. ^Yoshida K, Sakurai Y, Kawahara S, et al. (2008). "Anaphylaxis to polyvinylpyrrolidone in povidone-iodine for impetigo contagiosum in a boy with atopic dermatitis".International Archives of Allergy and Immunology.146 (2):169–73.doi:10.1159/000113522.PMID 18204285.S2CID 25078233.
  24. ^Adachi A, Fukunaga A, Hayashi K, Kunisada M, Horikawa T (March 2003). "Anaphylaxis to polyvinylpyrrolidone after vaginal application of povidone-iodine".Contact Dermatitis.48 (3):133–6.doi:10.1034/j.1600-0536.2003.00050.x.PMID 12755725.S2CID 22975127.
  25. ^Rönnau AC, Wulferink M, Gleichmann E, et al. (November 2000). "Anaphylaxis to polyvinylpyrrolidone in an analgesic preparation".The British Journal of Dermatology.143 (5):1055–8.doi:10.1046/j.1365-2133.2000.03843.x.PMID 11069520.S2CID 10543466.
  26. ^abBruusgaard-Mouritsen MA, Mortz C, Winther L, Lene Heise Garvey LH (May 2021). "Repeated idiopathic anaphylaxis caused by povidone".Annals of Allergy, Asthma & Immunology.126 (5):598–600.doi:10.1016/j.anai.2021.01.030.PMID 33545346.
  27. ^Katelaris, Constance (2009)."'Iodine Allergy' label is misleading".Australian Prescriber.32 (5):125–128.doi:10.18773/austprescr.2009.061.
  28. ^van Ketel WG, van den Berg WH (January 1990). "Sensitization to povidone-iodine".Dermatologic Clinics.8 (1):107–9.doi:10.1016/S0733-8635(18)30531-X.PMID 2302848.
  29. ^Wohlfarth, C (2010). "Thermodynamic Properties of Polymer Solutions.".Landolt-Börnstein, New Series, Group VIII, Volume 6D. Landolt-Börnstein - Group VIII Advanced Materials and Technologies. Vol. 6D2. Springer Verlag. pp. 1266–1267.Bibcode:2010LanB..6D2.1266W.doi:10.1007/978-3-642-02890-8_752.ISBN 978-3-642-02889-2.
  30. ^Sapir, L.; Stanley, CB.; Harries, D. (2016). "Properties of Polyvinylpyrrolidone in a Deep Eutectic Solvent".J. Phys. Chem. A.120 (19):3253–3259.Bibcode:2016JPCA..120.3253S.doi:10.1021/acs.jpca.5b11927.OSTI 1424493.PMID 26963367.
  31. ^Song, Guoshan; Lin, Yannan; Zhu, Zhongcheng; Zheng, Heying; Qiao, Jinping; He, Changcheng; Wang, Huiliang (2015). "Strong Fluorescence of Poly(N-vinylpyrrolidone) and Its Oxidized Hydrolyzate".Macromolecular Rapid Communications.36 (3):278–85.doi:10.1002/marc.201400516.PMID 25420749.
  32. ^Fischer, Frank; Bauer, Stephan (2009). "Polyvinylpyrrolidon. Ein Tausendsassa in der Chemie".Chemie in unserer Zeit.43 (6):376–383.doi:10.1002/ciuz.200900492.
  33. ^Koczkur, Kallum M.; Mourdikoudis, Stefanos; Polavarapu, Lakshminarayana; Skrabalak, Sara E. (2015)."Polyvinylpyrrolidone (PVP) in nanoparticle synthesis"(PDF).Dalton Transactions.44 (41):17883–17905.doi:10.1039/C5DT02964C.PMID 26434727.S2CID 9323765.
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