Dimethylolpropionic acid (DMPA) is a chemical compound that has the full
IUPAC
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
name of 2,2-bis(hydroxymethyl)propionic acid and is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with one carboxyl and two hydroxy groups. It has the
CAS Registry Number of 4767-03-7.
Properties
DMPA is an odorless free flowing white crystalline solid and essentially non-toxic. DMPA has two different functional groups hydroxyl and carboxylic acid so the molecule can be used for a wide variety of syntheses. In addition to reaction with other chemicals, DMPA can also react with itself to produce
ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
s via esterification, as one example.
Uses
One key use of DMPA is in the field of coatings and adhesives. It is used as a modifier in the production of anionic
Polyurethane dispersion
Polyurethane dispersion, or PUD, is understood to be a polyurethane polymer resin dispersed in water, rather than a solvent, although some cosolvent may be used. Its manufacture involves the synthesis of polyurethanes having carboxylic acid functi ...
s. Solvent soluble binders/resins for coatings can be converted into an aqueous binder with the use of this material. In this case it is reacted with a suitable diisocyanate such as
isophorone diisocyanate
Isophorone diisocyanate (IPDI) is an organic compound in the class known as isocyanates. More specifically, it is an Aliphatic compound, aliphatic diisocyanate. It is produced in relatively small quantities, accounting for (with hexamethylene diis ...
or
TMXDI usually along with other
polyol
In organic chemistry, a polyol is an organic compound containing multiple hydroxyl groups (). The term "polyol" can have slightly different meanings depending on whether it is used in food science or polymer chemistry. Polyols containing two, th ...
s to make a
prepolymer
In polymer chemistry, the term prepolymer or pre-polymer, refers to a monomer or system of monomers that have been reacted to an intermediate-molecular mass state. This material is capable of further polymerization by reactive groups to a fully c ...
.
There is also the possibility of using 2,2-bis(hydroxymethyl)propionic acid for the synthesis of dendrimeric molecules, also known as hyperbranched molecules. When each hydroxyl group is reacted with 2,2-bis (hydroxymethyl) propionic acid, the number of hydroxyl groups present in the molecule doubles. Repeating this reaction step, produces one more shell each time and thus the molecule grows. If at the end the hydroxyl groups are reacted with a bifunctional component, dendrimeric UV binders can be produced, for example. Dendrimeric molecules have low solution viscosities and improved properties.
It has a wide variety of other uses including production of hyperbranched polyesters, waterborne polyesters, waterbased alkyd resins, and aqueous epoxy resins. It has even found use in
polyethylene terephthalate
Polyethylene terephthalate (or poly(ethylene terephthalate), PET, PETE, or the obsolete PETP or PET-P), is the most common thermoplastic polymer resin of the polyester family and is used in synthetic fibre, fibres for clothing, packaging, conta ...
fiber production. Another use is in the medical field for drug release purposes. In the business world it has been cited as an outstanding growth opportunity
See also
*
Prepolymer
In polymer chemistry, the term prepolymer or pre-polymer, refers to a monomer or system of monomers that have been reacted to an intermediate-molecular mass state. This material is capable of further polymerization by reactive groups to a fully c ...
*
Waterborne resins Waterborne resins are sometimes called water-based resins. They are resins or polymeric resins that use water as the carrying medium as opposed to solvent or solvent-less. Resins are used in the production of coatings, adhesives, sealants, elastomer ...
References
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External links
NISTPubChemFabrichem websiteTechnical Data Sheet
Beta hydroxy acids
Coatings