| Revision as of 13:41, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 463467546 of page Polyvinyl_alcohol for the Chem/Drugbox validation project (updated: 'ChEMBL', 'KEGG'). |
Latest revision as of 18:38, 29 November 2024 edit 46.253.36.102 (talk) →UsesTags: Mobile edit Mobile web edit |
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{{distinguish|polyvinyl acetate}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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| verifiedrevid = 458439742 |
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| verifiedrevid = 464210395 |
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| ImageFile = Pva.png |
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| Name = |
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| ImageFile = Polyvinyl Alcohol Structural Formula V1.svg |
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| IUPACName = |
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| ImageSize = 150px |
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| OtherNames = PVOH; Poly(Ethenol), Ethenol, homopolymer; PVA; Polyviol; Vinol; Alvyl; Alkotex; Covol; Gelvatol; Lemol; Mowiol |
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| ImageFile1 = Sample of Polyvinyl alcohol.jpg |
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| Section1 = {{Chembox Identifiers |
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| ImageSize1 = 120px |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| IUPACName = |
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| OtherNames = PVOH; Poly(Ethenol), Ethenol, homopolymer; PVA; Polyviol; Vinol; Alvyl; Alcotex; Covol; Gelvatol; Lemol; Mowiol; Mowiflex, Alcotex, Elvanol, Gelvatol, Lemol, Nelfilcon A, Polyviol und Rhodoviol |
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| SystematicName = |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 9002-89-5 |
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| CASNo = 9002-89-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = |
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| UNII = 1E30GE2EF7 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = NA |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = none |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 76101 --> |
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| ChEMBL = 76101 |
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| RTECS =TR8100000 |
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| RTECS =TR8100000 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = <!-- blanked - oldvalue: C00980 --> |
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| KEGG = C00980 |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula = (]<sub>2</sub>]<sub>4</sub>])<sub>x</sub> |
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| Formula = (]<sub>2</sub>]<sub>4</sub>])<sub>x</sub> |
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| Density = 1.19-1.31 g/cm³ |
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| Density = 1.19–1.31 g/cm<sup>3</sup> |
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| MeltingPt = 230°C |
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| MeltingPtC = 200 |
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| Solubility = |
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| BoilingPt = 228°C |
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| RefractIndex = 1.477 @ 632 nm<ref>{{cite journal | vauthors = Schnepf MJ, Mayer M, Kuttner C, Tebbe M, Wolf D, Dulle M, Altantzis T, Formanek P, Förster S, Bals S, König TA, Fery A | display-authors = 3 | title = Nanorattles with tailored electric field enhancement | journal = Nanoscale | volume = 9 | issue = 27 | pages = 9376–9385 | date = July 2017 | pmid = 28656183 | doi = 10.1039/C7NR02952G | doi-access = free | hdl = 10067/1447970151162165141 | hdl-access = free }}</ref> |
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| LogP =0.26 <ref>{{Cite web|url=https://www.chemsrc.com/en/cas/9002-89-5_342468.html|title=Poly(vinyl alcohol)|publisher=ChemSrc}}</ref> |
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| NFPA-H = 1 |
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| NFPA-H = 0 |
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| NFPA-F = 0 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| NFPA-R = 0 |
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| NFPA-O =0 |
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| FlashPt = 79.44°C |
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| FlashPtC = 79.44 |
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| LD50 =14,700 mg/kg (Mouse) |
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| LD50 =14,700 mg/kg (mouse) |
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'''Polyvinyl alcohol''' ('''PVOH''', '''PVA''', or '''PVAl''') is a ]-] ]. It has the idealized formula <sub>''n''</sub>. It is used in ], ], as a thickener and emulsion stabilizer in ] (PVAc) adhesive formulations, in a variety of coatings, and ]. It is colourless (white) and odorless. It is commonly supplied as beads or as solutions in water.<ref name=Ullmann/><ref>{{cite journal | vauthors = Tang X, Alavi S |doi=10.1016/j.carbpol.2011.01.030 |title=Recent Advances in Starch, Polyvinyl Alcohol Based Polymer Blends, Nanocomposites and Their Biodegradability |journal=Carbohydrate Polymers |volume=85 |pages=7–16 |year=2011 }}</ref> Without an externally added crosslinking agent, PVA solution can be gelled through repeated freezing-thawing, yielding highly strong, ultrapure, ] ]s which have been used for a variety of applications such as ], ]s, ]es, etc.<ref>{{Cite journal|last1=Adelnia|first1=Hossein|last2=Ensandoost|first2=Reza|last3=Shebbrin Moonshi|first3=Shehzahdi|last4=Gavgani|first4=Jaber Nasrollah|last5=Vasafi|first5=Emad Izadi|last6=Ta|first6=Hang Thu|display-authors=3|date=2022-02-05|title=Freeze/thawed polyvinyl alcohol hydrogels: Present, past and future|url=https://www.sciencedirect.com/science/article/pii/S0014305721007084|journal=European Polymer Journal|language=en|volume=164|pages=110974|doi=10.1016/j.eurpolymj.2021.110974|bibcode=2022EurPJ.16410974A |s2cid=245576810 |issn=0014-3057|hdl=10072/417476|hdl-access=free}}</ref> |
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Although polyvinyl alcohol is often referred to by the ] PVA, more generally PVA refers to ], which is commonly used as a wood adhesive and sealer. |
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==Uses== |
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PVA is used in a variety of medical applications because of its biocompatibility, low tendency for protein adhesion, and low toxicity. Specific uses include ] replacements, ]es, ]s and ]s.<ref>{{cite journal |vauthors = Baker MI, Walsh SP, Schwartz Z, Boyan BD |title = A review of polyvinyl alcohol and its uses in cartilage and orthopedic applications |journal = Journal of Biomedical Materials Research Part B: Applied Biomaterials |volume = 100 |issue = 5 |pages = 1451–7 |date = July 2012 |pmid = 22514196 |doi = 10.1002/jbm.b.32694 }}</ref> Polyvinyl alcohol is used as an aid in ]s. Its largest application in China is its use as a ] to make PVAc dispersions. In Japan its major use is the production of ] fiber.<ref name="sri">, published March 2007, abstract retrieved July 30, 2008.</ref> This fiber is also manufactured in ] for self-sufficiency reasons, because no ] is required to produce it. Another application is photographic film.<ref>{{Cite book |title=Characterization and Failure Analysis of Plastics |chapter=Effects of Composition, Processing, and Structure on Properties of Engineering Plastics|editor-last=Lampman |editor-first=Steve |publisher=ASM International |year=2003 |page=29|doi=10.31399/asm.tb.cfap.t69780028|isbn=978-0-87170-789-5}}</ref> |
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PVA-based polymers are used widely in additive manufacturing. For example, 3D printed oral dosage forms demonstrate great potential in the pharmaceutical industry. It is possible to create drug-loaded tablets with modified drug-release characteristics where PVA is used as a binder substance.<ref>{{cite journal |vauthors = Xu X, Zhao J, Wang M, Wang L, Yang J |display-authors=3|title = 3D Printed Polyvinyl Alcohol Tablets with Multiple Release Profiles |journal = Scientific Reports |volume = 9 |issue = 1 |pages = 12487 |date = August 2019 |pmid = 31462744 |pmc = 6713737 |doi = 10.1038/s41598-019-48921-8 |bibcode=2019NatSR...912487X}}</ref> |
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Medically, PVA-based ]s have received ] ] approval to be used as ] particles to be used for peripheral hypervascular tumors.<ref>{{Cite web |title=Contour™ - Brief Summary |url=https://www.bostonscientific.com/en-US/products/embolization/contour-pva-embolization-particles/contour-prescriptive-information.html |access-date=2023-08-11 |website=www.bostonscientific.com |language=en-us}}</ref> It may also used as the embolic agent in a Uterine Fibroid Embolectomy (UFE).<ref>{{cite web |title = Uterine Fibroid Embolization and Imaging |url = https://emedicine.medscape.com/article/421734-overview#a4 |vauthors = Siskin GP |veditors = Cho KJ |work=Medscape|publisher = WebMD LLC |archive-url=https://web.archive.org/web/20150304224753/https://emedicine.medscape.com/article/421734-overview#a15 |archive-date=2015-03-04}}</ref> In biomedical engineering research, PVA has also been studied for ], ] applications,<ref>{{Cite journal |last1=Baker |first1=Maribel I. |last2=Walsh |first2=Steven P. |last3=Schwartz |first3=Zvi |last4=Boyan |first4=Barbara D. |date=July 2012 |title=A review of polyvinyl alcohol and its uses in cartilage and orthopedic applications |url=https://onlinelibrary.wiley.com/doi/10.1002/jbm.b.32694 |journal=Journal of Biomedical Materials Research Part B: Applied Biomaterials |language=en |volume=100B |issue=5 |pages=1451–1457 |doi=10.1002/jbm.b.32694|pmid=22514196 }}</ref> and potential materials for ].<ref>{{Cite journal |last1=Chaouat |first1=Marc |last2=Le Visage |first2=Catherine |last3=Baille |first3=Wilms E. |last4=Escoubet |first4=Brigitte |last5=Chaubet |first5=Frédéric |last6=Mateescu |first6=Mircea Alexandru |last7=Letourneur |first7=Didier |date=2008-10-09 |title=A Novel Cross-linked Poly(vinyl alcohol) (PVA) for Vascular Grafts |url=https://onlinelibrary.wiley.com/doi/10.1002/adfm.200701261 |journal=Advanced Functional Materials |language=en |volume=18 |issue=19 |pages=2855–2861 |doi=10.1002/adfm.200701261|s2cid=42332293 }}</ref> |
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PVA is commonly used in household sponges that absorb more water than ] sponges.{{citation needed|date=August 2024}} |
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PVA may be used as an adhesive during preparation of ] for microscopic examination in ].<ref>{{cite journal|last1=Jensen|first1=B.|last2=Kepley|first2=W.|last3=Guarner|first3=J.|last4=Anderson|first4=K.|last5=Anderson|first5=D.|last6=Clairmont|first6=J.|last7=De l'aune|first7=W.|last8=Austin|first8=E.H.|last9=Austin|first9=G.E.|title=Comparison of Polyvinyl Alcohol Fixative with Three Less Hazardous Fixatives for Detection and Identification of Intestinal Parasites|journal=Journal of Clinical Microbiology|volume=38|issue=4|pages=1592–1598|doi=10.1128/jcm.38.4.1592-1598.2000|pmc=86497|pmid=10747149|year=2000}}</ref> |
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===Polyvinyl acetals=== |
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Polyvinyl ] are prepared by treating PVA with ]s. ] and ] afford ] (PVB) and ] (PVF), respectively. Preparation of polyvinyl butyral is the largest use for polyvinyl alcohol in the US and Western Europe. |
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==Preparation== |
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Unlike most ]s, PVA is not prepared by ] of the corresponding ], since the monomer, ], is thermodynamically unstable with respect to its ]ization to ]. Instead, PVA is prepared by hydrolysis of polyvinyl acetate,<ref name=Ullmann>{{Ullmann |first1=Manfred L. |last1=Hallensleben| name-list-style = vanc |title=Polyvinyl Compounds, Others |year=2000 |doi=10.1002/14356007.a21_743}}</ref> or sometimes other vinyl ester-derived polymers with ] or ] groups instead of acetate. The conversion of the polyvinyl esters is usually conducted by base-catalysed ] with ethanol: |
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: <sub>''n''</sub> + C<sub>2</sub>H<sub>5</sub>OH → <sub>''n''</sub> + C<sub>2</sub>H<sub>5</sub>OAc |
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The properties of the polymer are affected by the degree of transesterification. |
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Worldwide consumption of polyvinyl alcohol was over one million metric tons in 2006.<ref name="sri"/> Large producers include ] and ], while mainland China has installed a number of very large production facilities in the past decade{{clarify|date=June 2021}} and currently accounts for 45% of world capacity. |
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==Structure and properties== |
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PVA is an ] material that exhibits ]linity. In terms of microstructure, it is composed mainly of 1,3-diol linkages , but a few percent of 1,2-diols occur, depending on the conditions for the polymerization of the vinyl ester precursor.<ref name=Ullmann/> |
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Polyvinyl alcohol has excellent film-forming, ] and ] properties. It is also resistant to oil, grease and ]s. It has high tensile strength and flexibility, as well as high oxygen and aroma barrier properties. However, these properties are dependent on ]: water absorbed at higher humidity levels acts as a ], which reduces the polymer's tensile strength, but increases its elongation and tear strength. |
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==Safety and environmental considerations== |
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Polyvinyl alcohol is widely used, thus its toxicity and biodegradation are of interest. Tests showed that fish (guppies) are not harmed, even at a poly(vinyl alcohol) concentration of 500 mg/L of water.<ref name=Ullmann/> |
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There are several different grades of PVA depending on the degrees of polymerization and hydrolysis, which will affect their physical and chemical properties as well as their biodegradability.<ref name=Ullmann/> Aqueous solutions of PVA degrade faster, which is why PVA grades that are highly water-soluble tend to have a faster biodegradation.<ref>{{cite journal | vauthors = Kawai F, Hu X | title = Biochemistry of microbial polyvinyl alcohol degradation | journal = Applied Microbiology and Biotechnology | volume = 84 | issue = 2 | pages = 227–37 | date = August 2009 | pmid = 19590867 | doi = 10.1007/s00253-009-2113-6 | s2cid = 25068302 }}</ref> Not all PVA grades are readily biodegradable, but studies show that high water-soluble PVA grades such as the ones used in detergents can be readily biodegradable according to OECD |
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screening test conditions.<ref>Byrne, Dominic, Boeije, Geert, Croft, Ian, Hüttmann, Gerd, Luijkx, Gerard, Meier, Frank, Parulekar, Yash and Stijntjes, Gerard. "Biodegradability of Polyvinyl Alcohol Based Film Used for Liquid Detergent Capsules: Biologische Abbaubarkeit der für Flüssigwaschmittelkapseln verwendeten Folie auf Polyvinylalkoholbasis." Tenside Surfactants Detergents, vol. 58, no. 2, 2021, pp. 88-96. https://doi.org/10.1515/tsd-2020-2326</ref> |
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] PVA is relatively harmless.<ref name="study5">{{cite journal |last1=DeMerlis |first1=C. C. |last2=Schoneker |first2=D. R. |title=Review of the oral toxicity of polyvinyl alcohol (PVA) |journal=Food and Chemical Toxicology|date=March 2003 |volume=41 |issue=3 |pages=319–326 |doi=10.1016/s0278-6915(02)00258-2 |pmid=12504164 |url=https://pubmed.ncbi.nlm.nih.gov/12504164/ |access-date=17 January 2024 |issn=0278-6915}}</ref> The ] of polyvinyl alcohol is based on some of the following observations:<ref name="study5" /> |
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* The ] of polyvinyl alcohol is very low, with LD(50)s in the range of 15-20 g/kg; |
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* Orally administered PVA is very poorly absorbed from the ]; |
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* PVA does not accumulate in the ] when administered orally; |
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* Polyvinyl alcohol is not ] or ] |
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== See also == |
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* ] |
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* ] |
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== References == |
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{{reflist}} |
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== External links == |
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