Polyvinyl acetate

Last updated
Polyvinyl acetate
PVA.svg
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
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).
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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 (C4H6O2)n, it belongs to the polyvinyl ester family, with the general formula −[RCOOCHCH2]−. It is a type of thermoplastic. [1]

Contents

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

Related Research Articles

<span class="mw-page-title-main">Petrochemical</span> Chemical product derived from petroleum

Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.

<span class="mw-page-title-main">Celanese</span> American chemical company

Celanese Corporation, formerly known as Hoechst Celanese, is an American technology and specialty materials company headquartered in Irving, Texas. It is a Fortune 500 corporation. The company is the world's leading producer of acetic acid, producing about 1.95 million tonnes per year, representing approximately 25% of global production. Celanese is also the world's largest producer of vinyl acetate monomer (VAM).

PVA may refer to:

In polymer chemistry, emulsion polymerization is a type of radical polymerization that usually starts with an emulsion incorporating water, monomers, and surfactants. The most common type of emulsion polymerization is an oil-in-water emulsion, in which droplets of monomer are emulsified in a continuous phase of water. Water-soluble polymers, such as certain polyvinyl alcohols or hydroxyethyl celluloses, can also be used to act as emulsifiers/stabilizers. The name "emulsion polymerization" is a misnomer that arises from a historical misconception. Rather than occurring in emulsion droplets, polymerization takes place in the latex/colloid particles that form spontaneously in the first few minutes of the process. These latex particles are typically 100 nm in size, and are made of many individual polymer chains. The particles are prevented from coagulating with each other because each particle is surrounded by the surfactant ('soap'); the charge on the surfactant repels other particles electrostatically. When water-soluble polymers are used as stabilizers instead of soap, the repulsion between particles arises because these water-soluble polymers form a 'hairy layer' around a particle that repels other particles, because pushing particles together would involve compressing these chains.

<span class="mw-page-title-main">Polyvinyl fluoride</span> Chemical compound

Polyvinyl fluoride (PVF) or –(CH2CHF)n– is a polymer material mainly used in the flammability-lowering coatings of airplane interiors and photovoltaic module backsheets. It is also used in raincoats and metal sheeting. Polyvinyl fluoride is a thermoplastic fluoropolymer with a repeating vinyl fluoride unit, and it is structurally very similar to polyvinyl chloride.

<span class="mw-page-title-main">Polyvinyl alcohol</span> Chemical compound

Polyvinyl alcohol (PVOH, PVA, or PVAl) is a water-soluble synthetic polymer. It has the idealized formula [CH2CH(OH)]n. It is used in papermaking, textile warp sizing, as a thickener and emulsion stabilizer in polyvinyl acetate (PVAc) adhesive formulations, in a variety of coatings, and 3D printing. It is colourless (white) and odorless. It is commonly supplied as beads or as solutions in water. Without an externally added crosslinking agent, PVA solution can be gelled through repeated freezing-thawing, yielding highly strong, ultrapure, biocompatible hydrogels which have been used for a variety of applications such as vascular stents, cartilages, contact lenses, etc.

<span class="mw-page-title-main">Vinyl alcohol</span> Chemical compound

Vinyl alcohol, also called ethenol or ethylenol, is the simplest enol. With the formula CH2CHOH, it is a labile compound that converts to acetaldehyde immediately upon isolation near room temperature. It is not a practical precursor to any compound.

<span class="mw-page-title-main">Ethylene-vinyl acetate</span> Chemical compound

Ethylene-vinyl acetate (EVA), also known as poly(ethylene-vinyl acetate) (PEVA), is a copolymer of ethylene and vinyl acetate. The weight percent of vinyl acetate usually varies from 10 to 50%, with the remainder being ethylene. There are three different types of EVA copolymer, which differ in the vinyl acetate (VA) content and the way the materials are used.

<span class="mw-page-title-main">Vinyl acetate</span> Chemical compound

Vinyl acetate is an organic compound with the formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate, ethene-vinyl acetate copolymers, polyvinyl alcohol, and other important industrial polymers.

In polymer chemistry, vinyl polymers are a group of polymers derived from substituted vinyl monomers. Their backbone is an extended alkane chain [−CH2−CHR−]. In popular usage, "vinyl" refers only to polyvinyl chloride (PVC).

<span class="mw-page-title-main">Hot-melt adhesive</span> Glue applied by heating

Hot-melt adhesive (HMA), also known as hot glue, is a form of thermoplastic adhesive that is commonly sold as solid cylindrical sticks of various diameters designed to be applied using a hot glue gun. The gun uses a continuous-duty heating element to melt the plastic glue, which the user pushes through the gun either with a mechanical trigger mechanism on the gun, or with direct finger pressure. The glue squeezed out of the heated nozzle is initially hot enough to burn and even blister skin. The glue is sticky when hot, and solidifies in a few seconds to one minute. Hot-melt adhesives can also be applied by dipping or spraying, and are popular with hobbyists and crafters both for affixing and as an inexpensive alternative to resin casting.

<span class="mw-page-title-main">Acrylate polymer</span> Group of polymers prepared from acrylate monomers

An acrylate polymer is any of a group of polymers prepared from acrylate monomers. These plastics are noted for their transparency, resistance to breakage, and elasticity.

Wood glue is an adhesive used to tightly bond pieces of wood together. Many substances have been used as glues. Traditionally animal proteins like casein from milk or collagen from animal hides and bones were boiled down to make early glues. They worked by solidifying as they dried. Later, glues were made from plant starches like flour or potato starch. When combined with water and heated, the starch gelatinizes and forms a sticky paste as it dries. Plant-based glues were common for books and paper products, though they can break down more easily over time compared to animal-based glues. Examples of modern wood glues include polyvinyl acetate (PVA) and epoxy resins. Some resins used in producing composite wood products may contain formaldehyde. As of 2021, “the wood panel industry uses almost 95% of synthetic petroleum-derived thermosetting adhesives, mainly based on urea, phenol, and melamine, among others”.

Polyvinyl nitrate (abbreviated: PVN) is a high-energy polymer with the idealized formula of [CH2CH(ONO2)]. Polyvinyl nitrate is a long carbon chain (polymer) with nitrate groups bonded randomly along the chain. PVN is a white, fibrous solid, and is soluble in polar organic solvents such as acetone. PVN can be prepared by nitrating polyvinyl alcohol with an excess of nitric acid. Because PVN is also a nitrate ester such as nitroglycerin (a common explosive), it exhibits energetic properties and is commonly used in explosives and propellants.

Solution polymerization is a method of industrial polymerization. In this procedure, a monomer is dissolved in a non-reactive solvent that contains a catalyst or initiator.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC. Acetic acid is also known as acetyl hydroxide (AcOH).

<span class="mw-page-title-main">Conservation and restoration of ceramic objects</span> Preservation of heritage collections

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Formvar refers to any of several thermoplastic resins that are polyvinyl formals, which are polymers formed from polyvinyl alcohol and formaldehyde as copolymers with polyvinyl acetate. They are typically used as coatings, adhesives, and molding materials.

The conservation-restoration of panel paintings involves preventive and treatment measures taken by paintings conservators to slow deterioration, preserve, and repair damage. Panel paintings consist of a wood support, a ground, and an image layer. They are typically constructed of two or more panels joined together by crossbeam braces which can separate due to age and material instability caused by fluctuations in relative humidity and temperature. These factors compromise structural integrity and can lead to warping and paint flaking. Because wood is particularly susceptible to pest damage, an IPM plan and regulation of the conditions in storage and display are essential. Past treatments that have fallen out of favor because they can cause permanent damage include transfer of the painting onto a new support, planing, and heavy cradling. Today's conservators often have to remediate damage from previous restoration efforts. Modern conservation-restoration techniques favor minimal intervention that accommodates wood's natural tendency to react to environmental changes. Treatments may include applying flexible battens to minimize deformation or simply leaving distortions alone, instead focusing on preventive care to preserve the artwork in its original state.

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:
    • 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, "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. Young, M. E.; Murray, M.; Cordiner, P. (1999). "Stone consolidants and chemical treatments in Scotland". Robert Gordon University, Building Research Establishment and Historic Scotland. Archived from the original on 2016-11-17. Retrieved 2009-07-30.
  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. "Ultimate Materials Guide - Tips for 3D Printing with PVA".
  9. 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. Bibcode:2013InhTx..25S...6C. doi:10.3109/08958378.2013.854430. ISSN   1091-7691. PMID   24341843. S2CID   6414435.
  10. 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
  11. H. Staudinger, K. Frey, W. Stark, Ber. Deut. Chem. Ges. 1927, 60, 1782.