Premium
Photopolymerizable Synthons from Glycerol Derivatives
Author(s) -
Mhanna Ali,
Sadaka Faten,
Boni Gilles,
Brachais ClaireHélène,
Brachais Laurent,
Couvercelle JeanPierre,
Plasseraud Laurent,
Lecamp Laurence
Publication year - 2014
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-013-2375-0
Subject(s) - acryloyl chloride , photopolymer , monomer , chemistry , polymer chemistry , glycidol , photoinitiator , epichlorohydrin , organic chemistry , glycerol , condensation polymer , acrylate , catalysis , polymer
Photopolymerizable monomers based on monoglycerides were prepared by a convenient two‐step procedure. The first one consists of the synthesis of highly pure monoglycerides by an organocatalyzed solvent‐free route. This process was carried out by condensation of bio‐sourced carboxylic acids (i.e. butyric, decanoic, undecylenic or stearic acids) with glycerol carbonate or glycidol in the presence of a quaternary ammonium salt as a catalyst. The obtained bio‐based monoglycerides were modified in the second step by reaction with acryloyl and methacryloyl chloride leading to a series of new diacrylated and dimethacrylated monomers. The structures of the monoglycerides, diacrylated and dimethacrylated monomers were fully characterized by spectroscopic methods. Photopolymerization investigations monitored by infrared spectroscopy were achieved under ultraviolet radiation in the presence of a photoinitiator. The resulting cross‐linked materials were analyzed by thermal gravimetric analysis, gel content determination and tests of swelling in water, ethanol and methylene chloride. Data relative to the pendulum hardness of these materials are also included.