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{{lead too short|date=April 2015}}
{{lead too short|date=April 2015}}
{{chembox
{{chembox
| Verifiedfields = changed
|Verifiedfields = changed
| Watchedfields = changed
|Watchedfields = changed
| verifiedrevid = 477525539
|verifiedrevid = 477525539
| Name = Polyvinyl acetate
|Name = Polyvinyl acetate
| ImageFile = PVA.svg
|ImageFile = PVA.svg
| ImageSize = 150px
|ImageSize = 150px
| ImageName = Polyvinyl acetate
|ImageName = Polyvinyl acetate
| IUPACName = Poly[1-(acetyloxy)ethylene]
|IUPACName = Poly[1-(acetyloxy)ethylene]
|OtherNames = PVAc, PVA, Poly(ethenyl ethanoate), Poly(ethenyl acetate)
| SystematicName =
| OtherNames = PVAc, PVA, Poly(ethenyl ethanoate), Poly(ethenyl acetate)
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| SMILES = O([C@@H](C*)*)C(C)=O
|SMILES = O([C@@H](C*)*)C(C)=O
| CASNo_Ref = {{cascite|correct|CAS}}
|CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 9003-20-7
|CASNo = 9003-20-7
| UNII_Ref = {{fdacite|correct|FDA}}
|UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 32K497ZK2U
|UNII = 32K497ZK2U
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = none
|ChemSpiderID = none
| PubChem = 7758
|PubChem = 7758
| KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C12282
|KEGG = C12282
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| Formula =(C<sub>4</sub>H<sub>6</sub>O<sub>2</sub>)<sub>n</sub>
|Formula =(C<sub>4</sub>H<sub>6</sub>O<sub>2</sub>)<sub>n</sub>
| MolarMass = 86.09&nbsp;g/mol per unit
|MolarMass = 86.09&nbsp;g/mol per unit
|Density = 1.19&nbsp;g/cm<sup>3</sup> (25&nbsp;°C)
| Appearance =
|BoilingPtC = 112
| Density = 1.19&nbsp;g/cm<sup>3</sup> (25&nbsp;°C)
}}
| MeltingPtC =
|Section3={{Chembox Hazards
| BoilingPtC = 112
|ExternalSDS = [http://www.ampolymer.com/SDS/PolyvinylAcetateSDS.html MSDS]
}}
}}
|Section7={{Chembox Hazards
| ExternalSDS = [http://www.ampolymer.com/SDS/PolyvinylAcetateSDS.html MSDS]
| NFPA-H =
| NFPA-R =
| NFPA-F =
| HPhrases =
| PPhrases =
| GHS_ref =
| FlashPt =
| ExploLimits =
| AutoignitionPt =
}}
}}
}}


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== Properties ==
== Properties ==

The [[degree of polymerization]] of polyvinyl acetate is typically 100 to 5000, while its [[ester group]]s are sensitive to [[base hydrolysis]] and slowly convert PVAc into [[polyvinyl alcohol]] and [[acetic acid]].
The [[degree of polymerization]] of polyvinyl acetate is typically 100 to 5000, while its [[ester group]]s are sensitive to [[base hydrolysis]] and slowly convert PVAc into [[polyvinyl alcohol]] and [[acetic acid]].


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== Discovery ==
== Discovery ==

Polyvinyl acetate was discovered in [[Germany]] in 1912 by [[Fritz Klatte]].<ref>See:<br />
Polyvinyl acetate was discovered in [[Germany]] in 1912 by [[Fritz Klatte]].<ref>See:<br />
* Deutsche Reichs Patent no. 281687 (4 July 1913), ''Journal of the Society of Chemical Industry (London)'', vol.&nbsp;34, p.&nbsp;623 (1915);
* Deutsche Reichs Patent no. 281687 (4 July 1913), ''Journal of the Society of Chemical Industry (London)'', vol.&nbsp;34, p.&nbsp;623 (1915);
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== Preparation ==
== Preparation ==

PVA is a [[vinyl polymer]]. Polyvinyl acetate is prepared by the [[polymerization]] of [[vinyl acetate|vinyl acetate monomer]] ([[Radical (chemistry)|free-radical]] vinyl polymerization of the [[monomer]] vinyl acetate).
PVA is a [[vinyl polymer]]. Polyvinyl acetate is prepared by the [[polymerization]] of [[vinyl acetate|vinyl acetate monomer]] ([[Radical (chemistry)|free-radical]] vinyl polymerization of the [[monomer]] vinyl acetate).


== Applications ==
== Applications ==

As a [[Dispersion (chemistry)|dispersion]] in water (usually an emulsion), PVAc preparations are used as [[adhesive]]s for [[porosity|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 |authors=Young M. E., Murray M., Cordiner 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>
As a [[Dispersion (chemistry)|dispersion]] in water (usually an emulsion), PVAc preparations are used as [[adhesive]]s for [[porosity|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 |authors=Young M. E., Murray M., Cordiner 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>


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== See also ==
== See also ==

* [[Ethylene vinyl acetate]]
* [[Ethylene vinyl acetate]]
* [[International Klein Blue]]
* [[International Klein Blue]]
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[[Category:Woodworking adhesives]]
[[Category:Woodworking adhesives]]
[[Category:Wood finishing materials]]
[[Category:Wood finishing materials]]
[[Category:Polymers]]
[[Category:Acetate esters]]
[[Category:Acetate esters]]

Revision as of 17:40, 1 February 2023

Polyvinyl acetate
Polyvinyl acetate
Names
IUPAC name
Poly[1-(acetyloxy)ethylene]
Other names
PVAc, PVA, Poly(ethenyl ethanoate), Poly(ethenyl acetate)
Identifiers
3D model (JSmol)
ChemSpider
  • none
ECHA InfoCard 100.108.147 Edit this at Wikidata
KEGG
UNII
  • O([C@@H](C*)*)C(C)=O
Properties
(C4H6O2)n
Molar mass 86.09 g/mol per unit
Density 1.19 g/cm3 (25 °C)
Boiling point 112 °C (234 °F; 385 K)
Hazards
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Polyvinyl acetate (PVA, PVAc, poly(ethenyl ethanoate)), commonly known as wood glue, 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 (C4H6O2)n, it belongs to the polyvinyl ester family, with the general formula −[RCOOCHCH2]−. It is a type of thermoplastic.[1]

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.[2]

Discovery

Polyvinyl acetate was discovered in Germany in 1912 by Fritz Klatte.[3]

The monomer, vinyl acetate, was first produced on an industrial scale by the addition of acetic acid to acetylene with a mercury(I) salt,[4] 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.[5]

Uses:

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:

See also

References

  1. ^ Murray, G. T. (1997), Handbook of materials selection for engineering applications, CRC Press, p. 242, ISBN 978-0-8247-9910-6.
  2. ^ Francesca Cappitelli; Claudia Sorlini (2008). "Microorganisms Attack Synthetic Polymers in Items Representing Our Cultural Heritage". Applied and Environmental Microbiology. 74 (3): 564–569. Bibcode:2008ApEnM..74..564C. doi:10.1128/AEM.01768-07. PMC 2227722. PMID 18065627.
  3. ^ See:
    • Deutsche Reichs Patent no. 281687 (4 July 1913), Journal of the Society of Chemical Industry (London), vol. 34, p. 623 (1915);
    • Deutsche Reichs Patent no. 281688 (2 April 1914);
    • British Patent no. 15271 (25 June 1914.);
    • Fritz Klatte and Adolf Rollett, "Plastic composition and process of producing it" Archived 2017-05-10 at the Wayback Machine, 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).
  4. ^ Rutherford John Gettens and George Leslie Stout, Painting Materials: A Short Encyclopaedia (Princeton, New Jersey: D. Van Nostrand, 1942), page 74.
  5. ^ "Stone consolidants and chemical treatments in Scotland". Robert Gordon University, Building Research Establishment and Historic Scotland. 1999. Archived from the original on 2016-11-17. Retrieved 2009-07-30. {{cite web}}: Cite uses deprecated parameter |authors= (help)
  6. ^ "The Conservation of the Archimedes Palimpsest". The Walters Art Museum. 2011. Retrieved February 22, 2018.
  7. ^ Amann, Manfred; Minge, Oliver (2012). "Biodegradability of Poly(vinyl acetate) and Related Polymers". Advances in Polymer Science. 245: 137–172. doi:10.1007/12_2011_153. ISBN 978-3-642-27153-3.
  8. ^ Coggins, Christopher R. E.; Jerome, Ann M.; Lilly, Patrick D.; McKinney, Willie J.; Oldham, Michael J. (2013). "A comprehensive toxicological evaluation of three adhesives using experimental cigarettes". Inhalation Toxicology. 25 Suppl 2: 6–18. doi:10.3109/08958378.2013.854430. ISSN 1091-7691. PMID 24341843. S2CID 6414435.
  9. ^ Van den Berg, G. (2002-01-01), "Dutch-Type Cheeses", in Roginski, Hubert (ed.), Encyclopedia of Dairy Sciences, Oxford: Elsevier, pp. 371–378, ISBN 978-0-12-227235-6, retrieved 2021-12-10
  10. ^ H. Staudinger, K. Frey, W. Stark, Ber. Deut. Chem. Ges. 1927, 60, 1782.