Polyvinylpyrrolidone

Polyvinylpyrrolidone
Polyvinylpyrrolidone
IUPAC name
Polyvinylpyrrolidone
Other names
PVP, Povidone, Polyvidone

Poly[1-(2-oxo-1-pyrrolidinyl)ethylen] 1-Ethenyl-2-pyrrolidon homopolymer 1-Vinyl-2-pyrrolidinon-Polymere Copovidone

PNVP
Identifiers
CAS number 9003-39-8 YesY
Jmol-3D images Image 1
Properties
Molecular formula (C6H9NO)n
Molar mass 2.500 - 2.5000.000 g·mol−1
Appearance white to light yellow, hygroscopic, amorphous powder
Density 1.2 g/cm³
Melting point

150 - 180 °C (glass temperature)
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Polyvinylpyrrolidone (PVP), also commonly called Polyvidone or Povidone, is a water-soluble polymer made from the monomer N-vinylpyrrolidone:[1]

Polyvinylpyrrolidon synthese.svg

Contents

Properties

PVP is soluble in water and other polar solvents. When dry it is a light flaky powder, which readily absorbs 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.

History

PVP was first synthesized by Prof. Walter Reppe and a patent was filed in 1939 for one of the most interesting 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.[2]

Uses

The monomer is extremely toxic to aquatic life.

Medical

The polymer PVP was used as a blood plasma expander for trauma victims after the first half of the 20th century.

It is used as a binder in many pharmaceutical tablets;[3] it simply passes through the body when taken orally. However, autopsies have found that crospovidone does contribute to pulmonary vascular injury in substance abusers who have injected pharmaceutical tablets intended for oral consumption.[4] The long-term effects of crospovidone within the lung are unknown. PVP added to iodine forms a complex called povidone-iodine that possesses disinfectant properties.[5] This complex is used in various products like solutions, ointment, pessaries, liquid soaps and surgical scrubs. It is known for instance under the trade name Betadine.

It is used in pleurodesis (fusion of the pleura because of incessant pleural effusions). For this purpose, povidone iodine is equally effective and safe as talc, and may be preferred because of easy availability and low cost.[6]

Technical

PVP is also used in many technical applications:

Other uses

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

PVP is also used in personal care products, such as shampoos and toothpastes, in paints, and adhesives that must be moistened, such as old-style postage stamps and envelopes. It has also been used in contact lens solutions and in steel-quenching solutions.[9][10] PVP is the basis of the early formulas for hair sprays and hair gels, and still continues to be a component of some.

As a food additive, PVP is a stabilizer and has E number E1201. PVPP is E1202. It is also used in the wine industry as a fining agent for white wine or some beers. Other references state that polyvinyl pyrrolidone and its derivatives are fully from mineral synthetic[11] origin. Therefore, its use in the production should not be a problem for vegans.

In molecular biology, PVP can be used as a blocking agent during Southern blot analysis as a component of Denhardt'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.

In microscopy, PVP is useful for making an aqueous mounting medium.[12]

Safety

The U.S. Food and Drug Administration (FDA) has approved this chemical for many uses,[13] and it is generally considered safe. However, there have been documented cases of allergic reactions to PVP/povidone, particularly regarding subcutaneous (applied under the skin) use and situations where the PVP has come in contact with autologous serum (internal blood fluids) and mucous membranes. For example, a boy having an anaphylactic response after application of PVP-Iodine for treatment of impetigo was found to be allergic to the PVP component of the solution.[14] A woman, who had previously experienced urticaria (hives) from various hair products, later found to contain PVP, had an anaphylactic response after povidone-iodine solution was applied internally. She was found to be allergic to PVP.[15] In another case, a man experiencing anaphylaxis after taking acetaminophen tablets orally was found to be allergic to PVP.[16]

Povidone is commonly used in conjunction with other chemicals. Some of these, such as iodine, are blamed for allergic responses, although testing results in some patients show no signs of allergy to the suspect chemical. Allergies attributed to these other chemicals may possibly be caused by the PVP instead.[17][18]

Cross-linked derivatives

Main article: Polyvinylpolypyrrolidone

See also

2-Pyrrolidone

Notes

  1. ^ F. Haaf, A. Sanner and F. Straub (1985). "Polymers of N-Vinylpyrrolidone: Synthesis, Characterization and Uses". Polymer Journal 17 (1): 143–152. doi:10.1295/polymj.17.143. 
  2. ^ Fischer, Frank; Bauer, Stephan (2009). "Polyvinylpyrrolidon. Ein Tausendsassa in der Chemie". Chemie in unserer Zeit 43 (6): 376–383. doi:10.1002/ciuz.200900492. 
  3. ^ Bühler, Volker (2005). Excipients for Pharmaceuticals - Povidone, Crospovidone and Copovidone. Berlin, Heidelberg, New York: Springer. pp. 1–254. ISBN 978-3-540-23412. 
  4. ^ Santhi Ganesan M.D Embolized Crospovidone (poly[N-vinyl-2-pyrrolidone]) in the Lungs of Intravenous Drug Users Mod Pathol 2003;16(4):286–292 [1]
  5. ^ PVP-Iodine Accessed January 25, 2007
  6. ^ Das SK, Saha SK, Das A, Halder AK, Banerjee SN, Chakraborty M (September 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. 
  7. ^ United States Patent 6730316
  8. ^ http://pubs.acs.org/doi/abs/10.1021/ol9001398
  9. ^ Dr. Stephan Bauer, Dr. Frank Fischer (2009). Ein Polyvinylpyrrolidon (PVP): ein vielseitiges Spezialpolymer – Verwendung in der Keramik und als Metallabschreckmedium. 61. pp. 382–385. 
  10. ^ 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. 
  11. ^ http://www.ispcorp.com/products/pharma/content/brochure/plasdonePovidone/PlasdonePovidone.pdf
  12. ^ Lillie RD & Fullmer HM (1976) Histopathologic Technic and Practical Histochemistry, 4th ed. New York: McGraw-Hill, p.411. ISBN 0070378622.
  13. ^ 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: January 6, 2010. Database Last Updated: January 13, 2010. Available at http://www.accessdata.fda.gov/scripts/cder/iig/index.cfm Accessed April 7, 2010 - search on povidone for list of approved items
  14. ^ 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. 
  15. ^ 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. 
  16. ^ 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. 
  17. ^ Katelaris, Constance (2009). "'Iodine Allergy' label is misleading". Australian Prescriber, Vol. 32, 125-128. Available at http://www.australianprescriber.com/magazine/32/5/125/8/ Accessed April 7, 2010
  18. ^ van Ketel WG, van den Berg WH (January 1990). "Sensitization to povidone-iodine". Dermatologic Clinics 8 (1): 107–9. PMID 2302848. 

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