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 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 (in which all ...

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. Types of polyisoprene ...

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 thermosoftening 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 as ...

Properties

The

degree of polymerization The degree of polymerization, or DP, is the number of structural unit, 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 polymeriza ...

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 hydrolysi ...

and slowly convert PVAc into

polyvinyl alcohol Polyvinyl 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) a ...

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 compone ...

. The

glass transition The glass–liquid transition, or glass transition, is the gradual and Reversible reaction, reversible transition in amorphous solid, amorphous materials (or in amorphous regions within Crystallinity, semicrystalline materials) from a hard and rel ...

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; it has 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 three ...

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 orthoborate, trihydroxidoboron or boracic acid. It is usually encountered as colorless crystals or a white ...

borax The BORAX Experiments were a series of safety experiments on boiling water nuclear reactors conducted by Argonne National Laboratory in the 1950s and 1960s at the National Reactor Testing Station in eastern Idaho.

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 Slime or slimy may refer to: Science and technology Biology * Slime coat, the coating of mucus covering the body of all fish * Slime mold, an informal name for several eukaryotic organisms * Biofilm, or slime, a syntrophic community of micr ...

and Flubber. A number of microorganisms can degrade polyvinyl acetate. Most commonly, damage is caused by filamentous

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

; however,

algae Algae ( , ; : alga ) is an informal term for any organisms of a large and diverse group of photosynthesis, photosynthetic organisms that are not plants, and includes species from multiple distinct clades. Such organisms range from unicellular ...

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

lichen A lichen ( , ) is a hybrid colony (biology), colony of algae or cyanobacteria living symbiotically among hypha, filaments of multiple fungus species, along with yeasts and bacteria embedded in the cortex or "skin", in a mutualism (biology), m ...

s, and

bacteria Bacteria (; : bacterium) are ubiquitous, mostly free-living organisms often consisting of one Cell (biology), biological cell. They constitute a large domain (biology), domain of Prokaryote, prokaryotic microorganisms. Typically a few micr ...

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 lies between the Baltic Sea and the North Sea to the north and the Alps to the south. Its sixteen States of Germany, constituent states have a total popu ...

in 1912 by Fritz Klatte. The monomer,

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

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

acetylene Acetylene (Chemical nomenclature, systematic name: ethyne) is a 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 u ...

in the presence of a mercury(I) salt acting as a

catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

, but it is now primarily made by

palladium Palladium is a chemical element; it has symbol Pd and atomic number 46. It is a rare and lustrous silvery-white metal discovered in 1802 by the English chemist William Hyde Wollaston. He named it after the asteroid Pallas (formally 2 Pallas), ...

-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 bond, carbon–carbon doub ...

Preparation

PVA is a vinyl polymer. 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 fo ...

of vinyl acetate monomer (

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 spont ...

vinyl polymerization of the

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

vinyl acetate).

Applications

As a dispersion 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 advantage ...

s for porous materials, particularly for

wood Wood is a structural tissue/material found as xylem in the stems and roots of trees and other woody plants. It is an organic materiala natural composite of cellulosic fibers that are strong in tension and embedded in a matrix of lignin t ...

paper Paper is a thin sheet material produced by mechanically or chemically processing cellulose fibres derived from wood, Textile, rags, poaceae, grasses, Feces#Other uses, herbivore dung, or other vegetable sources in water. Once the water is dra ...

, and

cloth Textile is an umbrella term that includes various fiber-based materials, including fibers, yarns, filaments, threads, and different types of fabric. At first, the word "textiles" only referred to woven fabrics. However, weaving is n ...

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

sandstone Sandstone is a Clastic rock#Sedimentary clastic rocks, clastic sedimentary rock composed mainly of grain size, sand-sized (0.0625 to 2 mm) silicate mineral, silicate grains, Cementation (geology), cemented together by another mineral. Sand ...

. PVAc is considered a food-safe material, and is thus used often in such applications (e.g., in food packaging material). Uses: * As

wood glue 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 w ...

, 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 building a book, usually in codex format, from an ordered stack of paper sheets with one's hands and tools, or in modern publishing, by a series of automated processes. Firstly, one binds the sheets of papers alon ...

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

acidic An acid is a molecule or ion capable of either donating a proton (i.e. hydrogen cation, H+), known as a Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid. The first category of acids are the ...

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. * In

handicrafts A handicraft is a traditional main sector of craft making and applies to a wide range of creative and design activities that are related to making things with one's hands and skill, including work with textiles, moldable and rigid material ...

. * 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 (message), letter or Greeting card, card. Traditional envelopes are made from sheets of paper cut to one o ...

adhesive. * As wallpaper adhesive. * As a primer for drywall 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 tex ...

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

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

coatings,

paint Paint is a material or mixture that, when applied to a solid material and allowed to dry, adds a film-like layer. As art, this is used to create an image or images known as a painting. Paint can be made in many colors and types. Most paints are ...

and other industrial coatings, as a binder in

nonwoven Nonwoven fabric or non-woven 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 in ...

s in glass fibers, sanitary napkins,

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 typically different pulp (paper), paper pulps. The pulp may be ...

and in textile finishing. Polyvinyl acetate is also the raw material to make other polymers like: *

Polyvinyl alcohol Polyvinyl 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) a ...

− 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 "molecule of high relative molecular mass, the structure of which essentially comprises the multiple repetition of units derived, actually or conceptually, from molecules of low relative molecular mass." Polymers are physi ...

.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.

References

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

Properties

Discovery

Preparation

Applications

See also

References