1,6-Hexanediol diacrylate
{{Chembox
| ImageFile = Hexandioldiacrylat.svg
| ImageSize =
| ImageAlt =
| PIN = Hexane-1,6-diyl di(prop-2-enoate)
| OtherNames = HDDA, HDODA
| Section1 = {{Chembox Identifiers
| CASNo = 13048-33-4
| PubChem = 25644
| EC_number = 235-921-9
| UNNumber = 3082
| UNII = FY751V5MMY
| DTXSID = DTXSID9025401
| ChEMBL = 1530684
| ChemSpiderID = 23890
| StdInChI=1S/C12H18O4/c1-3-11(13)15-9-7-5-6-8-10-16-12(14)4-2/h3-4H,1-2,5-10H2
| StdInChIKey = FIHBHSQYSYVZQE-UHFFFAOYSA-N
| SMILES = C=CC(=O)OCCCCCCOC(=O)C=C
}}
| Section2 = {{Chembox Properties
| C=12 | H=18 | O=4
| Appearance = Colorless oil
| Density =
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| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
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| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|317|319}}
| PPhrases = {{P-phrases|261|264|272|280|302+352|305+351+338|321|332+313|333+313|337+313|362|363|501}}
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1,6-Hexanediol diacrylate (HDDA or HDODA) is a difunctional acrylate ester monomer used in the manufacture of polymers.{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/25644|title=1,6-Hexanediol diacrylate|last=PubChem|website=pubchem.ncbi.nlm.nih.gov|language=en|access-date=2020-02-12}}{{Cite web|url=http://www.chemspider.com/Chemical-Structure.23890.html|title=1,6-Hexanediol diacrylate {{!}} C12H18O4 {{!}} ChemSpider|website=www.chemspider.com|access-date=2020-02-12}} It is particularly useful for use in ultraviolet light cure applications.{{Cite web|url=https://ir.uiowa.edu/cgi/viewcontent.cgi?article=3559&context=etd|title=Industrially relevant epoxy-acrylate hybrid resin photopolymerizations|last=Ajiboye|first=Gbenga|date=2012|website=|url-status=dead|archive-url=https://web.archive.org/web/20131125034635/http://ir.uiowa.edu:80/cgi/viewcontent.cgi?article=3559&context=etd |archive-date=2013-11-25 |access-date=}} Furthermore, it is also used in adhesives, sealants, alkyd coatings, elastomers, photopolymers, and inks for improved adhesion, hardness, abrasion and heat resistance.{{Citation|title=Abrasion Resistance Testing-Vehicle Exterior Graphics and Pin Striping|publisher=SAE International|doi=10.4271/j1847_198906}} Like other acrylate monomers it is usually supplied with a radical inhibitor such as hydroquinone added.{{Cite web|url=https://www.alfa.com/en/catalog/043203/|title=13048-33-4 - 1,6-Hexanediol diacrylate, 99% (reactive esters), stab. with 90ppm hydroquinone - HDODA - 43203 - Alfa Aesar|website=www.alfa.com|access-date=2020-02-27}}
Preparation
The material is prepared by acid-catalyzed esterification of 1,6-hexanediol with acrylic acid.{{Ullmann|doi=10.1002/14356007.a01_161.pub2|isbn=3527306730|title=Acrylic Acid and Derivatives|year=2003|last1=Ohara|first1=Takashi|last2=Sato|first2=Takahisa|last3=Shimizu|first3=Noboru|last4=Prescher|first4=Günter|last5=Schwind|first5=Helmut|last6=Weiberg|first6=Otto|last7=Marten|first7=Klaus|last8=Greim|first8=Helmut}}
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.{{Cite web|url=https://www.hexion.com/en-us/chemistry/epoxy-resins-curing-agents-modifiers/multi-functional-and-specialty-resins/epoxy-polyacrylates|title=Epoxy Polyacrylate Resins|website=www.hexion.com|access-date=2020-02-12}}
See also
- TMPTA (trimethylolpropane triacrylate), a triacrylate crosslinker
- Pentaerythritol tetraacrylate, a tetraacrylate crosslinker
References
{{Reflist}}
External links
- [https://www.ashland.com/file_source/Ashland/Documents/Sustainability/rc_hexanediol_diacrylate.pdf Product Stewardship Information]
{{DEFAULTSORT:Hexanediol diacrylate, 1, 6-}}