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1,6-Hexanediol diacrylate

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1,6-Hexanediol diacrylate
Names
Preferred IUPAC name
Hexane-1,6-diyl di(prop-2-enoate)
Other names
HDDA, HDODA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.032.641 Edit this at Wikidata
EC Number
  • 235-921-9
UNII
UN number 3082
  • InChI=1S/C12H18O4/c1-3-11(13)15-9-7-5-6-8-10-16-12(14)4-2/h3-4H,1-2,5-10H2
    Key: FIHBHSQYSYVZQE-UHFFFAOYSA-N
  • C=CC(=O)OCCCCCCOC(=O)C=C
Properties
C12H18O4
Molar mass 226.27 g/mol
Appearance colorless oil
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H317, H319
P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,6-Hexanediol diacrylate (HDDA or HDODA) is a difunctional acrylate ester monomer used in the manufacture of polymers.[1][2] It is particularly useful for use in ultraviolet light cure applications.[3] Furthermore, it is also used in adhesives, sealants, alkyd coatings, elastomers, photopolymers, and inks for improved adhesion, hardness, abrasion and heat resistance.[4] Like other acrylate monomers it is usually supplied with a radical inhibitor such as hydroquinone added.[5]

Preparation

The material is prepared by acid-catalyzed esterification of 1,6-hexanediol with acrylic acid.[6]

Other uses

As the molecule has acrylic functionality, it is capable of undergoing the Michael reaction with an amine. This allows it use in epoxy chemistry where its use speeds up the cure time considerably.[7]

See also

References

  1. ^ PubChem. "1,6-Hexanediol diacrylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-02-12.
  2. ^ "1,6-Hexanediol diacrylate | C12H18O4 | ChemSpider". www.chemspider.com. Retrieved 2020-02-12.
  3. ^ Ajiboye, Gbenga (2012). "Industrially relevant epoxy-acrylate hybrid resin photopolymerizations". Archived from the original on 2013-11-25.
  4. ^ Abrasion Resistance Testing-Vehicle Exterior Graphics and Pin Striping, SAE International, doi:10.4271/j1847_198906
  5. ^ "13048-33-4 - 1,6-Hexanediol diacrylate, 99% (reactive esters), stab. with 90ppm hydroquinone - HDODA - 43203 - Alfa Aesar". www.alfa.com. Retrieved 2020-02-27.
  6. ^ Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut (2003). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_161.pub2. ISBN 3527306730.
  7. ^ "Epoxy Polyacrylate Resins". www.hexion.com. Retrieved 2020-02-12.


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