Green Approach of Photoinitiated Polymerization Using Monomers Derived from Oleic Acid and Ionic Liquid

Abstract

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® TPOÀ 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 hydroxyfunctionalized derivative and hexandiol-1,6-dimethacrylate although the maximum of the polymerization rate was lower for the bio-based monomers indicating their lower reactivity.

Photoinitiated polymerization of methacrylates comprising phenyl moieties

“…23,24 Both photoinitiators show a comparable efficiency for example in photoinitiation of (meth)acrylates derived from oleic acid. 15 Therefore, these photoinitiators were selected for investigation of photoinitiated polymerization of the new 4-(4-methacryloyloxyphenyl)-butan-2-one (1) and the commercial 2-phenoxyethyl methacrylate (2) and phenyl methacrylate (3) depicted in Scheme 1. The commercial monomers 2 and 3 were selected for comparison because they are methacrylates containing an aromatic structure as well.…”

“…Photoinitiated polymerization has been of growing interest caused by increasing application areas that include for example coatings, inks, adhesives, varnishes, stereolithography, 3D print, laser printing imaging, dentistry, and microelectronics. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] Photoinitiated processes can be carried out at any temperature, although processing at room temperature can be seen as the preferred option.…”

“…Thus, (meth)acrylates derived from oleic acid and methacrylated alkyd resins have been investigated in photoinitiated polymerization recently. 11,13,15 The poly(meth)acrylates obtained by photoinitiated polymerization of (meth)acrylates derived from oleic acid exhibit mostly a low glass transition temperature that is caused by the flexible aliphatic structures. In contrast to this, polymethacrylates comprising aromatic structures possess higher glass transition temperature.…”

“…Currently, monomers derived from renewable materials are preferred over traditional monomers, which originate from petrochemical sources. Thus, (meth)acrylates derived from oleic acid and methacrylated alkyd resins have been investigated in photoinitiated polymerization recently 11,13,15 . The poly(meth)acrylates obtained by photoinitiated polymerization of (meth)acrylates derived from oleic acid exhibit mostly a low glass transition temperature that is caused by the flexible aliphatic structures.…”

A Green Step to New Monomers and Their Polymerization

“…Classical free radical polymerization is widely used in industry because this economically priced method can be applied for various monomers . An advantage of photoinitiated radical polymerization compared to classical free radical polymerization using a thermal initiator is the significantly higher polymerization rate and the possibility to select e. g. room temperature for polymerization . Therefore, polymerization using light is more efficient compared to thermal processes.…”