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{{Short description|Adhesive used for porous materials}} |
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{{Refimprove|date=June 2010}} |
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{{distinguish|Polyvinyl alcohol}} |
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{{chembox |
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{{chembox |
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|Watchedfields = changed |
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| verifiedrevid = 476996601 |
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|verifiedrevid = 477525539 |
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| Name = Polyvinyl acetate |
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|Name = Polyvinyl acetate |
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| ImageFile = PVA.svg |
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|ImageFile = PVA.svg |
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| ImageSize = 150px |
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| ImageName = Polyvinyl acetate |
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|ImageSize = 150px |
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|ImageName = Polyvinyl acetate |
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| IUPACName = poly (1-acetyloxiethylene) |
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|IUPACName = Poly |
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|OtherNames = PVAc, PVA, Poly(ethenyl ethanoate), Poly(ethenyl acetate) |
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| SystematicName = |
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|Section1={{Chembox Identifiers |
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| OtherNames = PVAc, PVA |
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|SMILES = O((C*)*)C(C)=O |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 9003-20-7 |
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|CASNo = 9003-20-7 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII = 32K497ZK2U |
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| ChemSpiderID = NA |
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|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| PubChem = 7758 |
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|ChemSpiderID = none |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = C12282 |
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|PubChem = 7758 |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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}} |
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|KEGG = C12282 |
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| Section2 = {{Chembox Properties |
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}} |
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| Empirical Formula = (C<sub>4</sub>H<sub>6</sub>O<sub>2</sub>)<sub>n</sub> |
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|Section2={{Chembox Properties |
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| MolarMass = 86.09 g/mol/unit |
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|Formula =(C<sub>4</sub>H<sub>6</sub>O<sub>2</sub>)<sub>n</sub> |
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| Appearance = |
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|MolarMass = 86.09 g/mol per unit |
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| Density = |
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|Density = 1.19 g/cm<sup>3</sup> (25 °C) |
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| MeltingPtC = |
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| BoilingPtC = |
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|BoilingPtC = 112 |
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}} |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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|ExternalSDS = |
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}} |
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| NFPA-H = |
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'''Polyvinyl acetate''', '''PVA''', '''PVAc''', '''poly(ethenyl ethanoate)''', is a ]y ] with the formula (C<sub>4</sub>H<sub>6</sub>O<sub>2</sub>)<sub>n</sub>. It belongs to the ]s family with the general formula --. It is a type of ].<ref>{{Citation | last = Murray | first = G. T. | title = Handbook of materials selection for engineering applications | page = 242 | publisher = CRC Press | year = 1997 | url = http://books.google.com/books?id=NC-AXM9U6qsC&pg=PA242 | isbn = 9780824799106 | postscript =.}}</ref> |
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'''Polyvinyl acetate''' ('''PVA''', '''PVAc''', '''poly(ethenyl ethanoate)'''), commonly known as '''wood glue''' (a term that may also refer to ]), '''PVA glue''', '''white glue''', '''carpenter's glue''', '''school glue''', or ] in the US, is a widely available adhesive used for porous materials like wood, paper, and cloth. An ] ]y ] with the formula (C<sub>4</sub>H<sub>6</sub>O<sub>2</sub>)<sub>''n''</sub>, it belongs to the ] family, with the general formula −−. It is a type of ].<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> |
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== Properties == |
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It should not be confused with the related polymer ], which is called PVA also (PVAc could be considered a technically correct abbreviation for polyvinyl acetate and would aid in avoiding such confusion). |
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The ] of polyvinyl acetate is typically 100 to 5000, while its ]s are sensitive to ] and slowly convert PVAc into ] and ]. |
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The ] temperature of polyvinyl acetate is between 30 and 45 °C depending on the molecular weight. |
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Polyvinyl acetate is a component of a widely-used type of glue, referred to variously as '''wood glue''', '''white glue''', '''carpenter's glue''', '''school glue''' or '''PVA glue'''. |
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PVAc dispersions such as ] contain polyvinyl alcohol as a ]. In alkaline conditions, ] compounds such as ] or ] cause the polyvinyl alcohol to ], forming tackifying precipitates or toys, such as ] and ]. |
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==Preparation== |
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A number of microorganisms can degrade polyvinyl acetate. Most commonly, damage is caused by filamentous ]; however, ], ]s, ]s, and ] 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> |
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PVAc is a vinyl polymer. Polyvinyl acetate is prepared by ] of ] ( ] vinyl polymerization of the ] vinyl acetate). |
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== Discovery == |
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== Discovery == |
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Polyvinyl acetate was discovered in ] in 1912 by ].<ref>See: |
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Polyvinyl acetate was discovered in ] in 1912 by Dr. ].<ref>See:<br />'''(1)''' Deutsche Reichs Patent no. 281687 (4 July 1913), an abstract of which appears in the ''Journal of the Society of Chemical Industry (London)'', vol. 34, page 623 (1915);<br />'''(2)''' Deutsche Reichs Patent no. 281688 (2 April 1914);<br />'''(3)''' British patent no. 15271 (25 June 1914.); <br />'''(4)''' Fritz Klatte and Adolf Rollett, U.S. Patent 1,241,738 (filed: July 3, 1914; issued: Oct. 2, 1917), an abstract of which appears in the ''Journal of the Society of Chemical Industry (London)'', vol. 36, page 1185 (1917).</ref> |
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* Deutsches Reichspatent no. 281687 (4 July 1913), ''Journal of the Society of Chemical Industry (London)'', vol. 34, p. 623 (1915); |
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* Deutsches Reichspatent no. 281688 (2 April 1914); |
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* British patent no. 15271 (25 June 1914.); |
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* Fritz Klatte and Adolf Rollett, {{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=2017-05-10 }}, U.S. Patent 1,241,738 (filed: July 3, 1914; issued: Oct. 2, 1917), an abstract of which appears in the ''Journal of the Society of Chemical Industry (London)'', vol. 36, p. 1185 (1917).</ref> |
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The monomer, vinyl acetate, was on an industrial scale first produced by addition of ] to ] with a mercury(I) salt<ref>Rutherford John Gettens and George Leslie Stout, ''Painting Materials: A Short Encyclopaedia'' (Princeton, New Jersey: D. Van Nostrand, 1942),.</ref> but it is now primarily made by ] catalyzed oxidative addition of acetic acid to ]. |
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The monomer, ], was first produced on an industrial scale by the addition of ] to ] with a mercury(I) salt,<ref>Rutherford John Gettens and George Leslie Stout, ''Painting Materials: A Short Encyclopaedia'' (Princeton, New Jersey: D. Van Nostrand, 1942), .</ref> but it is now primarily made by ]-catalyzed oxidative addition of ] to ]. |
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==Properties== |
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== Preparation == |
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PVA is a ]. Polyvinyl acetate is prepared by the ] of ] (] vinyl polymerization of the ] vinyl acetate). |
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The degree of polymerization of polyvinyl acetate typically is 100 to 5000. |
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The ester groups of the polyvinyl acetate are sensitive for ] and will slowly convert PVAc into polyvinyl alcohol and ]. |
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== Applications == |
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Under alkaline conditions, ] compounds, such as ] or ] causes the polymer to ] forming tackifying precipitates or ]. |
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As a ] in water (usually an emulsion), PVAc preparations are used as ]s for ] materials, particularly for ], ], and ], and as a consolidant for porous building stone, in particular ].<ref name="Report">{{cite web |url=http://www2.rgu.ac.uk/schools/mcrg/miconsol.htm |title=Stone consolidants and chemical treatments in Scotland |publisher=], Building Research Establishment and Historic Scotland |last1=Young|first1=M. E.|last2=Murray|first2=M.|last3=Cordiner|first3=P. |year=1999 |access-date=2009-07-30 |archive-url=https://web.archive.org/web/20161117184257/http://www2.rgu.ac.uk/schools/mcrg/miconsol.htm |archive-date=2016-11-17 |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=Mar 22, 2024 |website=www.accessdata.fda.gov |publisher=DEPARTMENT OF HEALTH AND HUMAN SERVICES |
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|access-date= Sep 25, 2024 |quote=}}</ref> and is thus used often in such applications (e.g., in food packaging material). |
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== Applications and uses == |
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As an ] in water, PVAc emulsions are used as ]s for ] materials, particularly for ], ], and ], and as a consolidant for porous building stone, in particular ].<ref name="Report">{{cite web|url=http://www2.rgu.ac.uk/schools/mcrg/miconsol.htm|title=Stone consolidants and chemical treatments in Scotland|publisher=], Building Research Establishment and Historic Scotland|author=Young, M.E., M. Murray and P. Cordiner|year=1999|accessdate=2009-07-30}}</ref> |
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Uses: |
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Uses: |
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* as ] PVAc is known as "white glue" and the yellow "]" or PVA glue. |
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* As ], PVAc is known as "white glue" and the yellow as "carpenter's glue". |
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* as paper adhesive during paper packaging converting |
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* As paper adhesive during paper packaging conversion. |
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* in ] and book arts, due to its flexible strong bond and non-] nature (unlike many other polymers). The use of PVAC on the ] 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. |
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* In ] and book arts, due to its flexible strong bond and non-] nature (unlike many other polymers). The use of PVAc on the ] 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=] |date=2011 |access-date=February 22, 2018}}</ref> |
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* for ]ed works. |
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* In ]. |
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* as ] adhesives, |
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* As ] adhesive. |
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* as ] |
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* As ]. |
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* As a ] for ] and other substrates. |
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* As a gum base in ].<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> |
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* As a water-soluble support material for ], usually for the ] method.<ref>{{cite web | url=https://www.simplify3d.com/resources/materials-guide/pva/ | title=Ultimate Materials Guide - Tips for 3D Printing with PVA }}</ref> |
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* As an adhesive for ].<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> |
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* As the coating layer on ].<ref>{{Citation|last=Van den Berg|first=G.|title=Dutch-Type Cheeses|date=2002-01-01|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=2021-12-10}}</ref> |
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The stiff ] PVAc , but mostly the more soft ] a combination of vinyl acetate and ethylene, ] (VAE), is used also in ] coatings, ] and other industrial coatings, as binder in ]s in ]s. ], ] and in ] |
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The stiff ] PVAc, but mostly the softer ], a combination of vinyl acetate and ethylene, ] (VAE), is also used in ] coatings, ] and other industrial coatings, as a binder in ]s in ]s, ], ] and in ]. |
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PVAc can also be used as coating to protect ] from ] and ]{{Citation needed|date=August 2007}}. |
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Polyvinyl acetate is also the raw material to make other polymers like: |
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Polyvinyl acetate is also the raw material to make other polymers like: |
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* ] --: Polyvinyl acetate is partially or completely ] to give polyvinyl alcohol. This reversible saponification and esterification reaction was a strong hint for ] in the formulation of his theory of ].<ref>H. Staudinger, K. Frey, W. Stark, Ber. Deut. Chem. Ges. 1927, 60, 1782.</ref> |
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* ] −−: Polyvinyl acetate is partially or completely ] to give polyvinyl alcohol. This reversible saponification and esterification reaction was a strong hint for ] in the formulation of his theory of ].<ref>H. Staudinger, K. Frey, W. Stark, Ber. Deut. Chem. Ges. 1927, 60, 1782.</ref> |
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* ] (PVAP): Polyvinyl acetate is partially hydrolyzed and then esterified with ]. |
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* ] (PVAP): Polyvinyl acetate is partially hydrolyzed and then esterified with ]. |
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==See also== |
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== See also == |
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*]: ] |
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==References== |
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== References == |
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{{Reflist}} |
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{{reflist}} |
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{{Authority control}} |
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{{DEFAULTSORT:Polyvinyl Acetate}} |
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