4-Hydroxybutylacrylat - 4-Hydroxybutylacrylat

Structural formula
Structural formula of 4-hydroxybutyl acrylate
General
Name 4-Hydroxybutylacrylat
other names
  • 4-HBA
  • Hydroxybutylacrylat
  • Butandiol-1,4-monoacrylat
Sum formula C 7 H 12 O 3
Brief description

colorless and odorless liquid [1]

External identifiers / databases
CAS number 2478-10-6
EC number 219-606-3
ECHA-InfoCard 100.017.825
PubChem 75588
Wikidata Q27260261
characteristics
Molar mass 144.2 g · mol −1
Physical state

liquid

density

1,041 g·cm−3[1]

Melting point

−80 °C[1]

boiling point

236 °C[1]

Vapor pressure

0.000104 Pa (25 ° C) [1]

Refractive index

1,452 (20 °C)[2]

safety instructions
GHS hazard labeling [1]
07 - Warning 05 - Corrosive

danger

H and P phrases H: 302​‐​315​‐​318​‐​317
P: 261​‐​280​‐​305+351+338 [2]
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 . [3]

Extraction and presentation

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

Synthesis of 4-HBA

characteristics

When reacting with isocyanates , hydroxybutyl acrylate has the highest reactivity of the common hydroxyl group-containing acrylate monomers. This is based on the one hand on the electron-donating effect of the hydrocarbon chains and on the other hand on the better availability for the reaction. This means that a hydroxyl group on a long hydrocarbon chain has a much better mobility and can thus meet an isocyanate group more easily. It is more reactive than 2-hydroxypropyl acrylate and 2-hydroxyethyl acrylate . [3]

use

Hydroxybutyl acrylate can be incorporated into binders such as polyacrylates via free-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 . [3]

Isocyanate crosslinking of 4-HBA

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 .