{{Short description|Adhesive used for porous materials}} {{distinguish|Polyvinyl alcohol}} {{Use dmy dates|date=March 2026}} {{chembox |Verifiedfields = changed |Watchedfields = changed |verifiedrevid = 477525539 |Name = Polyvinyl acetate |ImageFile = PVA.svg |ImageSize = 150px |ImageName = Polyvinyl acetate |IUPACName = Poly[1-(acetyloxy)ethylene] |OtherNames = PVAc, PVA, Poly(ethenyl ethanoate), Poly(ethenyl acetate) |Section1={{Chembox Identifiers |SMILES = O([C@@H](C*)*)C(C)=O |CASNo_Ref = {{cascite|correct|CAS}} |CASNo = 9003-20-7 |UNII_Ref = {{fdacite|correct|FDA}} |UNII = 32K497ZK2U |ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |ChemSpiderID = none |PubChem = 7758 |KEGG_Ref = {{keggcite|correct|kegg}} |KEGG = C12282 }} |Section2={{Chembox Properties |Formula =(C<sub>4</sub>H<sub>6</sub>O<sub>2</sub>)<sub>n</sub> |MolarMass = 86.09 g/mol per unit |Density = 1.19 g/cm<sup>3</sup> (25 °C)
}} |Section3={{Chembox Hazards |ExternalSDS = [http://www.ampolymer.com/SDS/PolyvinylAcetateSDS.html MSDS] }} }}
'''Polyvinyl acetate''' ('''PVA''', '''PVAc''', '''poly(ethenyl ethanoate)'''), commonly known as '''wood glue''' (a term that may also refer to other types of glues), '''PVA glue''', '''white glue''', '''carpenter's glue''', '''school glue''', or Elmer's Glue in the US, is a widely available adhesive used for porous materials like wood, paper, and cloth. An aliphatic rubbery synthetic polymer with the formula (C<sub>4</sub>H<sub>6</sub>O<sub>2</sub>)<sub>''n''</sub>, it belongs to the polyvinyl ester family, with the general formula −[RCOOCHCH<sub>2</sub>]−. It is a type of thermoplastic.<ref>{{Citation | last = Murray | first = G. T. | title = Handbook of materials selection for engineering applications | page = 242 | publisher = CRC Press | year = 1997 | url = https://books.google.com/books?id=NC-AXM9U6qsC&pg=PA242 | isbn = 978-0-8247-9910-6 | postscript =.}}</ref>
== Properties == The degree of polymerization of polyvinyl acetate is typically 100 to 5000, while its ester groups are sensitive to base hydrolysis and slowly convert PVAc into polyvinyl alcohol and acetic acid.
The glass transition temperature of polyvinyl acetate is between 30 and 45 °C depending on the molecular weight.
PVAc dispersions such as Elmer's Glue-All contain polyvinyl alcohol as a protective colloid. In alkaline conditions, boron compounds such as boric acid or borax cause the polyvinyl alcohol to cross-link, forming tackifying precipitates or toys, such as Slime and Flubber.
A number of microorganisms can degrade polyvinyl acetate. Most commonly, damage is caused by filamentous fungi; however, algae, yeasts, lichens, and bacteria can also degrade polyvinyl acetate.<ref>{{cite journal |pmc=2227722 |title=Microorganisms Attack Synthetic Polymers in Items Representing Our Cultural Heritage |author1=Francesca Cappitelli |author2=Claudia Sorlini |journal=Applied and Environmental Microbiology |date=2008 |volume=74 |issue=3 |pmid=18065627 |doi=10.1128/AEM.01768-07 |pages=564–569|bibcode=2008ApEnM..74..564C }}</ref>
== Discovery == Polyvinyl acetate was discovered in Germany in 1912 by Fritz Klatte.<ref>See: * Deutsches Reichspatent no. 281687 (4 July 1913), ''Journal of the Society of Chemical Industry (London)'', vol. 34, p. 623 (1915); * Deutsches Reichspatent no. 281688 (2 April 1914); * British patent no. 15271 (25 June 1914.); * Fritz Klatte and Adolf Rollett, [http://patimg1.uspto.gov/.piw?Docid=01241738&homeurl=http%3A%2F%2Fpatft.uspto.gov%2Fnetacgi%2Fnph-Parser%3FSect1%3DPTO2%2526Sect2%3DHITOFF%2526p%3D1%2526u%3D%25252Fnetahtml%25252FPTO%25252Fsearch-adv.htm%2526r%3D1%2526f%3DG%2526l%3D50%2526d%3DPALL%2526S1%3D01241738%2526OS%3DPN%2F01241738%2526RS%3DPN%2F01241738&PageNum=&Rtype=&SectionNum=&idkey=NONE&Input=View+first+page "Plastic composition and process of producing it"] {{Webarchive|url=https://web.archive.org/web/20170510073454/http://patimg1.uspto.gov/.piw?Docid=01241738&homeurl=http%3A%2F%2Fpatft.uspto.gov%2Fnetacgi%2Fnph-Parser%3FSect1%3DPTO2%2526Sect2%3DHITOFF%2526p%3D1%2526u%3D%25252Fnetahtml%25252FPTO%25252Fsearch-adv.htm%2526r%3D1%2526f%3DG%2526l%3D50%2526d%3DPALL%2526S1%3D01241738%2526OS%3DPN%2F01241738%2526RS%3DPN%2F01241738&PageNum=&Rtype=&SectionNum=&idkey=NONE&Input=View+first+page |date=10 May 2017 }}, U.S. Patent 1,241,738 (filed: 3 July 1914; issued: 2 October 1917), an abstract of which appears in the ''Journal of the Society of Chemical Industry (London)'', vol. 36, p. 1185 (1917).</ref>
The monomer, vinyl acetate, was first produced on an industrial scale by the addition of acetic acid to acetylene in the presence of a mercury(I) salt acting as a catalyst,<ref>Rutherford John Gettens and George Leslie Stout, ''Painting Materials: A Short Encyclopaedia'' (Princeton, New Jersey: D. Van Nostrand, 1942), [https://books.google.com/books?id=bdQVgKWl3f4C&dq=Klatte&pg=PA74 page 74].</ref> but it is now primarily made by palladium-catalyzed oxidative addition of acetic acid to ethylene.
== Preparation == PVA is a vinyl polymer. Polyvinyl acetate is prepared by the polymerization of vinyl acetate monomer (free-radical vinyl polymerization of the monomer vinyl acetate).
== Applications == As a dispersion in water (usually an emulsion), PVAc preparations are used as adhesives for porous materials, particularly for wood, paper, and cloth, and as a consolidant for porous building stone, in particular sandstone.<ref name="Report">{{cite web |url=http://www2.rgu.ac.uk/schools/mcrg/miconsol.htm |title=Stone consolidants and chemical treatments in Scotland |publisher=Robert Gordon University, Building Research Establishment and Historic Scotland |last1=Young|first1=M. E.|last2=Murray|first2=M.|last3=Cordiner|first3=P. |year=1999 |access-date=30 July 2009 |archive-url=https://web.archive.org/web/20161117184257/http://www2.rgu.ac.uk/schools/mcrg/miconsol.htm |archive-date=17 November 2016 |url-status=dead}}</ref> PVAc is considered a food-safe material,<ref>{{cite web |url=https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=175.300&SearchTerm=polyvinyl%20alcohol |title=CFR - Code of Federal Regulations Title 21 |author=<!--Not stated--> |date=22 March 2024 |website=www.accessdata.fda.gov |publisher=DEPARTMENT OF HEALTH AND HUMAN SERVICES |access-date= 25 September 2024 |quote=}}{{dead link|date=May 2025|bot=medic}}{{cbignore|bot=medic}}</ref> and is thus used often in such applications (e.g., in food packaging material).
Uses: * As wood glue, PVAc is known as "white glue" and the yellow as "carpenter's glue". * As paper adhesive during paper packaging conversion. * In bookbinding and book arts, due to its flexible strong bond and non-acidic nature (unlike many other polymers). The use of PVAc on the Archimedes Palimpsest during the 20th century greatly hindered the task of disbinding the book and preserving and imaging the pages in the early 21st century, in part because the glue was stronger than the parchment it held together.<ref>{{cite web |title=The Conservation of the Archimedes Palimpsest |url=http://archimedespalimpsest.org/about/conservation.php |publisher=The Walters Art Museum |date=2011 |access-date=22 February 2018}}</ref> * In handicrafts. * As envelope adhesive. * As wallpaper adhesive. * As a primer for drywall and other substrates. * As a gum base in chewing gum.<ref>{{Cite journal |last1=Amann |first1=Manfred |last2=Minge |first2=Oliver |date=2012 |title=Biodegradability of Poly(vinyl acetate) and Related Polymers |url=https://www.researchgate.net/publication/287603466 |journal=Advances in Polymer Science |volume=245 |pages=137–172 |doi=10.1007/12_2011_153|isbn=978-3-642-27153-3 }}</ref> * As an adhesive for cigarette paper.<ref>{{Cite journal |last1=Coggins |first1=Christopher R. E. |last2=Jerome |first2=Ann M. |last3=Lilly |first3=Patrick D. |last4=McKinney |first4=Willie J. |last5=Oldham |first5=Michael J. |date=2013 |title=A comprehensive toxicological evaluation of three adhesives using experimental cigarettes |journal=Inhalation Toxicology |volume=25 Suppl 2 |pages=6–18 |doi=10.3109/08958378.2013.854430 |issn=1091-7691 |pmid=24341843 |bibcode=2013InhTx..25S...6C |s2cid=6414435}}</ref> * As the coating layer on Gouda cheese.<ref>{{Citation|last=Van den Berg|first=G.|title=Dutch-Type Cheeses|date=1 January 2002|url=https://www.sciencedirect.com/science/article/pii/B0122272358000778|encyclopedia=Encyclopedia of Dairy Sciences|pages=371–378|editor-last=Roginski|editor-first=Hubert|place=Oxford|publisher=Elsevier|language=en|isbn=978-0-12-227235-6|access-date=10 December 2021}}</ref>
The stiff homopolymer PVAc, but mostly the softer copolymer, a combination of vinyl acetate and ethylene, vinyl acetate ethylene (VAE), is also used in paper coatings, paint and other industrial coatings, as a binder in nonwovens in glass fibers, sanitary napkins, filter paper and in textile finishing.
Polyvinyl acetate is also the raw material to make other polymers like: * Polyvinyl alcohol −[HOCHCH<sub>2</sub>]−: Polyvinyl acetate is partially or completely hydrolysed to give polyvinyl alcohol. This reversible saponification and esterification reaction was a strong hint for Hermann Staudinger in the formulation of his theory of macromolecules.<ref>H. Staudinger, K. Frey, W. Stark, Ber. Deut. Chem. Ges. 1927, 60, 1782.</ref> * Polyvinyl acetate phthalate (PVAP): Polyvinyl acetate is partially hydrolyzed and then esterified with phthalic acid.
== See also == * Ethylene vinyl acetate * International Klein Blue * Elmer's Products
== References ==
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Category:Adhesives Category:Household chemicals Category:Vinyl polymers Category:Woodworking adhesives Category:Wood finishing materials Category:Acetate esters