4-hydroxybutyl acrylate

Structural formula
General
Surname	4-hydroxybutyl acrylate
other names	4-HBA Hydroxybutyl acrylate 1,4-butanediol monoacrylate
Molecular formula	C 7 H 12 O 3
Brief description	colorless and odorless liquid
External identifiers / databases
CAS number 2478-10-6 EC number 219-606-3 ECHA InfoCard 100.017.825 PubChem 75588 Wikidata Q27260261
properties
Molar mass	144.2 g mol −1
Physical state	liquid
density	1.041 g cm −3
Melting point	−80 ° C
boiling point	236 ° C
Vapor pressure	0.000104 Pa (25 ° C)
Refractive index	1.452 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 302-315-318-317 P: 261-280-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

In 4-hydroxybutyl acrylate (4-HBA, 1,4-butanediol monoacrylate) is an ester of acrylic acid . It contains both a hydroxyl group and an unsaturated double bond . It is generally used as a monomer for different classes of binders .

Extraction and presentation

Hydroxybutyl acrylate is produced via the partial esterification of 1,4-butanediol with acrylic acid.

properties

When reacting with isocyanates , hydroxybutyl acrylate has the highest reactivity of the common hydroxyl-containing acrylate monomers. This is based on the one hand on the electron-donating effect of the hydrocarbon chains and on the other hand from the better availability for reaction. This means that a hydroxyl group on a long hydrocarbon chain has a much better mobility and can therefore meet an isocyanate group more easily. It is more reactive than 2-hydroxypropyl acrylate and 2-hydroxyethyl acrylate .

use

Hydroxybutyl acrylate can be incorporated into binders such as polyacrylates via radical or ionic polymerization . Since hydroxybutyl acrylate has a free hydroxyl group, it can be used to incorporate hydroxyl groups into resins. These groups are then available for curing reactions with isocyanates or urea resins .

Individual evidence

1. ↑ ^{a b c d e f} Entry on 4-hydroxybutyl acrylate in the GESTIS substance database of the IFA , accessed on June 13, 2018(JavaScript required) .
2. ↑ ^{a b} Data sheet 4-Hydroxybutyl acrylate from Sigma-Aldrich , accessed on June 14, 2018 ( PDF ).
3. ↑ ^{a b c} Roland Baumstark, Reinhold Schwalm and Manfred Schwartz: Acrylate resins . Vincentz Network, Hannover 2014, ISBN 978-3-86630-820-6 .
4. ↑ Ulrich Poth: Synthetic binders for coating systems . Vincentz Network, Hannover 2016, ISBN 978-3-86630-611-0 .