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Green Approach of Photoinitiated Polymerization Using Monomers Derived from Oleic Acid and Ionic Liquid
Author(s) -
Sanay Berran,
Strehmel Bernd,
Strehmel Veronika
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201902661
Subject(s) - photoinitiator , monomer , polymer chemistry , ionic liquid , polymerization , reactivity (psychology) , acrylate , photopolymer , methacrylate , methyl methacrylate , materials science , oleic acid , imidazole , chemistry , organic chemistry , polymer , catalysis , medicine , biochemistry , alternative medicine , pathology
Bio‐based monomers synthesized from oleic acid mix and nonvolatile ionic liquid monomers were investigated by photo‐DSC using 2,4,6‐trimethylbenzoylphenyl phosphinate (Irgacure® TPO−L) or dibenzoyldiethylgermane (Ivocerin®) as photoinitiator. The results were compared with those obtained for commercial hexanediol‐1,6‐di(meth)acrylate. The ionic liquid monomers ( N ‐octyl‐ N’ ‐vinylimidazolium bis(trifluoromethylsulfonyl)imide (NTf 2 ) and N ‐decyl‐ N’ ‐vinylimidazolium NTf 2 ) showed lower reactivity compared to the diacrylate and slightly higher reactivity than the methacrylates. The vinyl group bound at the imidazolium ring fully converted during photoinitiated polymerization as confirmed by 1 H NMR analysis. Final conversion was higher for the imidazole‐functionalized methacrylate derived from fatty acid compared to both the hydroxy‐functionalized derivative and hexandiol‐1,6‐dimethacrylate although the maximum of the polymerization rate was lower for the bio‐based monomers indicating their lower reactivity.