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 In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated, like hexane ...

rubber Rubber, also called India rubber, latex, Amazonian rubber, ''caucho'', or ''caoutchouc'', as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds. Thailand, Malaysia, and ...

y synthetic polymer with the formula (C₄H₆O₂)_''n'', it belongs to the polyvinyl ester family, with the general formula − COOCHCH₂��. It is a type of

thermoplastic A thermoplastic, or thermosoft plastic, is any plastic polymer material that becomes pliable or moldable at a certain elevated temperature and solidifies upon cooling. Most thermoplastics have a high molecular weight. The polymer chains associate ...

Properties

The

degree of polymerization The degree of polymerization, or DP, is the number of monomeric units in a macromolecule or polymer or oligomer molecule. For a homopolymer, there is only one type of monomeric unit and the ''number-average'' degree of polymerization is given by ...

of polyvinyl acetate is typically 100 to 5000, while its ester groups are sensitive to

base hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis i ...

and slowly convert PVAc into

polyvinyl alcohol Poly(vinyl alcohol) (PVOH, PVA, or PVAl) is a water- soluble synthetic polymer. It has the idealized formula H2CH(OH)sub>''n''. It is used in papermaking, textile warp sizing, as a thickener and emulsion stabilizer in polyvinyl acetate (PVAc) ...

and

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main componen ...

. The

glass transition The glass–liquid transition, or glass transition, is the gradual and reversible transition in amorphous materials (or in amorphous regions within semicrystalline materials) from a hard and relatively brittle "glassy" state into a viscous or ru ...

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 Boron is a chemical element with the symbol B and atomic number 5. In its crystalline form it is a brittle, dark, lustrous metalloid; in its amorphous form it is a brown powder. As the lightest element of the '' boron group'' it has t ...

compounds such as

boric acid Boric acid, more specifically orthoboric acid, is a compound of boron, oxygen, and hydrogen with formula . It may also be called hydrogen borate or boracic acid. It is usually encountered as colorless crystals or a white powder, that dissolve ...

borax Borax is a salt (ionic compound), a hydrated borate of sodium, with chemical formula often written . It is a colorless crystalline solid, that dissolves in water to make a basic solution. It is commonly available in powder or granular form ...

cause the polyvinyl alcohol to

cross-link In chemistry and biology a cross-link is a bond or a short sequence of bonds that links one polymer chain to another. These links may take the form of covalent bonds or ionic bonds and the polymers can be either synthetic polymers or natural ...

, 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 A fungus ( : fungi or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as a kingdom, separately fr ...

; however,

algae Algae (; singular alga ) is an informal term for a large and diverse group of photosynthetic eukaryotic organisms. It is a polyphyletic grouping that includes species from multiple distinct clades. Included organisms range from unicellular micr ...

yeast Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are estimated to constit ...

lichen A lichen ( , ) is a composite organism that arises from algae or cyanobacteria living among filaments of multiple fungi species in a mutualistic relationship.bacteria Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were am ...

can also degrade polyvinyl acetate.

Discovery

Polyvinyl acetate was discovered in

Germany Germany,, officially the Federal Republic of Germany, is a country in Central Europe. It is the second most populous country in Europe after Russia, and the most populous member state of the European Union. Germany is situated betwee ...

in 1912 by

Fritz Klatte Fritz Klatte (28 March 1880, Diepholz – 11 February 1934) was a German chemist and the discoverer of polyvinyl acetate, with German patent (GP 281687 1912) for its preparation from acetylene gas.See:(1) Deutsche Reichs Patent no. 281687 (4 ...

. The monomer,

vinyl acetate Vinyl acetate is an organic compound with the formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate and ethene-vinyl acetate copolymers, important industrial polymers. Production The worldwide production capacity of v ...

, was first produced on an industrial scale by the addition of

acetylene Acetylene ( systematic name: ethyne) is the chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure ...

with a mercury(I) salt, but it is now primarily made by

palladium Palladium is a chemical element with the symbol Pd and atomic number 46. It is a rare and lustrous silvery-white metal discovered in 1803 by the English chemist William Hyde Wollaston. He named it after the asteroid Pallas, which was itself ...

-catalyzed oxidative addition of

ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene ...

Preparation

PVA is a

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

. Polyvinyl acetate is prepared by the

polymerization In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many f ...

vinyl acetate monomer Vinyl acetate is an organic compound with the formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate and ethene-vinyl acetate copolymers, important industrial polymers. Production The worldwide production capacity of v ...

(

free-radical In chemistry, a radical, also known as a free radical, is an atom, molecule, or ion that has at least one unpaired valence electron. With some exceptions, these unpaired electrons make radicals highly chemically reactive. Many radicals spon ...

vinyl polymerization of the

monomer In chemistry, a monomer ( ; '' mono-'', "one" + '' -mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization. Classification ...

vinyl acetate).

Applications

As a

dispersion Dispersion may refer to: Economics and finance *Dispersion (finance), a measure for the statistical distribution of portfolio returns *Price dispersion, a variation in prices across sellers of the same item *Wage dispersion, the amount of variatio ...

in water (usually an emulsion), PVAc preparations are used as

adhesive Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advant ...

s for

porous Porosity or void fraction is a measure of the void (i.e. "empty") spaces in a material, and is a fraction of the volume of voids over the total volume, between 0 and 1, or as a percentage between 0% and 100%. Strictly speaking, some tests measure ...

materials, particularly for

wood Wood is a porous and fibrous structural tissue found in the stems and roots of trees and other woody plants. It is an organic materiala natural composite of cellulose fibers that are strong in tension and embedded in a matrix of lignin ...

paper Paper is a thin sheet material produced by mechanically or chemically processing cellulose fibres derived from wood, rags, grasses or other vegetable sources in water, draining the water through fine mesh leaving the fibre evenly distribu ...

, and

cloth Textile is an umbrella term that includes various fiber-based materials, including fibers, yarns, filaments, threads, different fabric types, etc. At first, the word "textiles" only referred to woven fabrics. However, weaving is not the ...

, and as a consolidant for porous building stone, in particular

sandstone Sandstone is a clastic sedimentary rock composed mainly of sand-sized (0.0625 to 2 mm) silicate grains. Sandstones comprise about 20–25% of all sedimentary rocks. Most sandstone is composed of quartz or feldspar (both silicat ...

. 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 Bookbinding is the process of physically assembling a book of codex format from an ordered stack of ''signatures'', sheets of paper folded together into sections that are bound, along one edge, with a thick needle and strong thread. Cheaper, b ...

and book arts, due to its flexible strong bond and non-

acidic In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a ...

nature (unlike many other polymers). The use of PVAc on the

Archimedes Palimpsest The Archimedes Palimpsest is a parchment codex palimpsest, originally a Byzantine Greek copy of a compilation of Archimedes and other authors. It contains two works of Archimedes that were thought to have been lost (the '' Ostomachion'' and ...

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. * In

handicrafts A handicraft, sometimes more precisely expressed as artisanal handicraft or handmade, is any of a wide variety of types of work where useful and decorative objects are made completely by one’s hand or by using only simple, non-automated re ...

. * As

envelope An envelope is a common packaging item, usually made of thin, flat material. It is designed to contain a flat object, such as a letter or card. Traditional envelopes are made from sheets of paper cut to one of three shapes: a rhombus, a ...

adhesive. * As

wallpaper adhesive Adhesive flakes that are mixed with water to produce wallpaper paste Wallpaper adhesive or wallpaper paste is a specific adhesive, based on modified starch, methylcellulose, or clay used to fix wallpaper to walls. Wallpaper pastes have a typical ...

. * As a

primer Primer may refer to: Arts, entertainment, and media Films * ''Primer'' (film), a 2004 feature film written and directed by Shane Carruth * ''Primer'' (video), a documentary about the funk band Living Colour Literature * Primer (textbook), a te ...

for

drywall Drywall (also called plasterboard, dry lining, wallboard, sheet rock, gypsum board, buster board, custard board, and gypsum panel) is a panel made of calcium sulfate dihydrate (gypsum), with or without additives, typically extruded between thic ...

and other substrates * As a gum base in

chewing gum Chewing gum is a soft, cohesive substance designed to be chewed without being swallowed. Modern chewing gum is composed of gum base, sweeteners, softeners/ plasticizers, flavors, colors, and, typically, a hard or powdered polyol coating. Its t ...

. * As an adhesive for cigarette paper. *As the coating layer on Gouda cheese. The stiff

homopolymer A polymer (; Greek '' poly-'', "many" + '' -mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic an ...

PVAc, but mostly the softer

copolymer In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are ...

, a combination of vinyl acetate and ethylene, vinyl acetate ethylene (VAE), is also used in

coatings,

paint Paint is any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is most commonly used to protect, color, or provide texture. Paint can be made in many ...

and other industrial coatings, as a binder in

nonwoven Nonwoven fabric is a fabric-like material made from staple fibre (short) and long fibres (continuous long), bonded together by chemical, mechanical, heat or solvent treatment. The term is used in the textile manufacturing industry to denote fabri ...

s in

glass fiber Glass fiber ( or glass fibre) is a material consisting of numerous extremely fine fibers of glass. Glassmakers throughout history have experimented with glass fibers, but mass manufacture of glass fiber was only made possible with the inventio ...

sanitary napkins A menstrual pad, or simply a pad, (also known as a sanitary pad, sanitary towel, sanitary napkin or feminine napkin) is an absorbent item worn by women in their underwear when menstruating, bleeding after giving birth, recovering from gynecol ...

filter paper Filter paper is a semi-permeable paper barrier placed perpendicular to a liquid or air flow. It is used to separate fine solid particles from liquids or gases. The raw materials are different Pulp (paper), paper pulps. The pulp may be made from soft ...

and in

textile finishing In textile manufacturing, finishing refers to the processes that convert the woven or knitted cloth into a usable material and more specifically to any process performed after dyeing the yarn or fabric to improve the look, performance, or "ha ...

. Polyvinyl acetate is also the raw material to make other polymers like: *

Polyvinyl alcohol Poly(vinyl alcohol) (PVOH, PVA, or PVAl) is a water- soluble synthetic polymer. It has the idealized formula H2CH(OH)sub>''n''. It is used in papermaking, textile warp sizing, as a thickener and emulsion stabilizer in polyvinyl acetate (PVAc) ...

− OCHCH₂��: Polyvinyl acetate is partially or completely hydrolysed to give polyvinyl alcohol. This reversible saponification and esterification reaction was a strong hint for

Hermann Staudinger Hermann Staudinger (; 23 March 1881 – 8 September 1965) was a German organic chemist who demonstrated the existence of macromolecules, which he characterized as polymers. For this work he received the 1953 Nobel Prize in Chemistry. He is also ...

in the formulation of his theory of

macromolecules A macromolecule is a very large molecule important to biophysical processes, such as a protein or nucleic acid. It is composed of thousands of covalently bonded atoms. Many macromolecules are polymers of smaller molecules called monomers. The ...

.H. Staudinger, K. Frey, W. Stark, Ber. Deut. Chem. Ges. 1927, 60, 1782. * Polyvinyl acetate phthalate (PVAP): Polyvinyl acetate is partially hydrolyzed and then esterified with

phthalic acid Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(CO2H)2. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. Phthalic acid ...

References

{{Authority control Adhesives Household chemicals Vinyl polymers Woodworking adhesives Wood finishing materials Polymers Acetate esters

Properties

Discovery

Preparation

Applications

See also

References