2-hydroxypropyl methacrylate

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Structural formula
Chemical structure of 2-hydroxypropyl methacrylate
Structural formula of 2-hydroxypropyl methacrylate
Surname 2-hydroxypropyl methacrylate
other names
  • 2-HPMA
  • 2-hydroxypropyl methacrylate
  • 2-hydroxypropyl methacrylate
Molecular formula C 7 H 12 O 3
External identifiers / databases
CAS number 923-26-2
EC number 213-090-3
ECHA InfoCard 100.011.901
PubChem 13539
Wikidata Q27124054
Molar mass 144.2 g mol −1
Physical state



1.029 g cm −3

boiling point

240 ° C

Vapor pressure

130 Pa (65 ° C)


107 g / l (in water at 20 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning


H and P phrases H: 317-319
P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

When 2-hydroxypropyl methacrylate (2-HPMA) is an ester of methacrylic acid . It contains both a hydroxyl group and an unsaturated double bond . It is generally used as a monomer for different classes of binders .


When reacting with isocyanates , 2-hydroxypropyl methacrylate has a rather low reactivity. The reason for a rather low reactivity is not a lack of electron-donating effect, but rather a steric hindrance and a low probability of reaction partners encountering the hydroxyl group. It is less reactive than 2-hydroxyethyl acrylate and than 4-hydroxybutyl acrylate . The heat of polymerization is −50.5 kJ mol −1 or −350 kJ kg −1 .


2-Hydroxypropyl methacrylate can be incorporated into binders such as polyacrylates via free-radical or ionic polymerization . Since 2-hydroxypropyl methacrylate has a free hydroxyl group, it can be used to build hydroxyl groups into resins. These groups are then available for curing reactions with isocyanates or urea resins .

Isocyanate crosslinking

In addition to the possibility of incorporating 2-hydroxypropyl methacrylate into resins via the double bond , there is also the possibility of doing this via the hydroxyl group. Example would be for this purpose, the reaction of 3 moles of 2-hydroxypropyl methacrylate and one mole of HDI - isocyanurate . This results in a urethane acrylate which can be used as a reactive diluent in coatings that can be cured by means of UV radiation .

Urethane acrylate

Individual evidence

  1. a b c d e Entry on 2-hydroxypropyl methacrylate in the GESTIS substance database of the IFA , accessed on June 17, 2018(JavaScript required) .
  2. Entry on 2-hydroxypropyl methacrylate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on June 25, 2018. Manufacturers or distributors can expand the harmonized classification and labeling .
  3. a b c d Baumstark, Roland, Schwalm, Reinhold, Schwartz, Manfred: Acrylate resins . Vincentz Network, Hannover 2014, ISBN 978-3-86630-820-6 , p. 32; 56; 267; 294 .
  4. Brandrup, J .; Immergut, EH; Grulke, EA; Abe, A .; Bloch, DR: Polymer Handbook , 4th Edition, Wiley-VCH 2003, ISBN 978-0-471-47936-9 , p. II / 369.