2-hydroxypropyl methacrylate

Structural formula
	Structural formula of 2-hydroxypropyl methacrylate
General
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
EC number	213-090-3
ECHA InfoCard	100.011.901
PubChem	13539
Wikidata	Q27124054
properties
Molar mass	144.2 g mol −1
Physical state	liquid
density	1.029 g cm −3
boiling point	240 ° C
Vapor pressure	130 Pa (65 ° C)
solubility	107 g / l (in water at 20 ° C)
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
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 .

properties

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 .

use

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 .

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 .

Individual evidence

↑ ^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) .
↑ 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 .
↑ ^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 .
↑ 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.

[GESTIS-1] Entry on 2-hydroxypropyl methacrylate in the GESTIS substance database of the IFA , accessed on June 17, 2018(JavaScript required) .

[CLP_100.011.901-2] 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 .

[Baumstark-3] Baumstark, Roland, Schwalm, Reinhold, Schwartz, Manfred: Acrylate resins . Vincentz Network, Hannover 2014, ISBN 978-3-86630-820-6 , p. 32; 56; 267; 294 .

[Polymer_Handbook-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.