1,6-Hexanediol diacrylate (HDDA or HDODA) is a difunctional acrylate ester monomer used in the manufacture of polymers. It is particularly useful for use in
ultraviolet
Ultraviolet radiation, also known as simply UV, is electromagnetic radiation of wavelengths of 10–400 nanometers, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight and constitutes about 10% of ...
light cure applications. Furthermore, it is also used in adhesives, sealants, alkyd coatings, elastomers, photopolymers, and inks for improved adhesion, hardness, abrasion and heat resistance. Like other acrylate monomers it is usually supplied with a radical inhibitor such as
hydroquinone
Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''para' ...
added.
Preparation
The material is prepared by acid-catalyzed esterification of
1,6-hexanediol
1,6-Hexanediol is an organic compound with the formula (CH2CH2CH2OH)2. It is a colorless water-soluble solid.
History and synthesis
W. H. Perkin Jr. and his graduate student Edward Haworth first prepared the compound in 1894 during their resea ...
with
acrylic acid
Acrylic acid (IUPAC: prop-2-enoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has ...
.
Other uses
As the molecule has acrylic functionality, it is capable of undergoing the
Michael reaction
In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a c ...
with an
amine
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...
. This allows it use in epoxy chemistry where its use speeds up the cure time considerably.
See also
*
TMPTA
Trimethylolpropane triacrylate (TMPTA) is a trifunctional acrylate ester monomer derived from trimethylolpropane, used in the manufacture of plastics, adhesives, acrylic glue, anaerobic sealants, and ink. It is useful for its low volatility an ...
(trimethylolpropane triacrylate), a triacrylate crosslinker
*
Pentaerythritol tetraacrylate, a tetraacrylate crosslinker
References
External links
Product Stewardship Information
{{DEFAULTSORT:Hexanediol diacrylate, 1, 6-
Acrylate esters
Monomers