Novel Hybrid Monomers Bearing Cycloaliphatic Epoxy and 1-Propenyl Ether Groups

Abstract

The synthesis of a novel series of hybrid monomers containing cationically polymerizable cycloaliphatic epoxide and 1-propenyl ether functional groups in the same molecule has been conducted. Detailed structure−reactivity studies of the diaryliodonium salt-induced cationic photopolymerizations of these monomers indicate that the rate of epoxide ring-opening polymerization is markedly enhanced by the presence of the 1-propenyl ether group. At the same time, the polymerization of the 1-propenyl ether groups in such hybrid monomers is retarded. A mechanism involving the free-radical-induced decomposition of the photoinitiator has been proposed which serves to amplify the rate of the photoinitiated cationic epoxide ring-opening polymerization.

Photochemical Production of Interpenetrating Polymer Networks; Simultaneous Initiation of Radical and Cationic Polymerization Reactions

“…Different examples can be given: acrylate/epoxide, (e.g., hexanediol diacrylate (HDDA)/3,4-epoxycyclohexylmethyl-3'4' epoxycyclohexyl carboxylate (EPOX)), trimethylolpropane triacrylate (TMPTA)/EPOX, TMPTA/diglycidyl ether of bisphenol A based epoxy resin EP, TMPTA/tri(ethylene glycol) divinyl ether (DVE-3), TMPTA/4-cyclo-hexane dimethanol divinyl ether (CHVE), fluorinated acrylate/epoxide, vinylether/acrylate, vinylether/maleate, vinylether/maleimide or oxetane/acrylate blends, (see e.g., in [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35]) anthracene-labeled polystyrene/methyl methacrylate MMA/ethylene glycol dimethacrylate [36], polyisobutene/polystyrene [37], polyacrylate/polybenzoxazine [38], acrylic/liquid crystals [39,40], 2-hydroxyethyl methacrylate/N-vinyl-2-pyrrolidone [41], polyurethane/poly(2-hydroxyethyl methacrylate) [42], calcium alginate/dextran-HEMA [43].…”

Interpenetrating Polymer Networks of Hydrocarbon and Fluorocarbon Polymers: Epoxy/Fluorinated Acrylic Macromonomers

“…UV radiation has already been used to produce IPNs. [2][3][4][5][6][7] The main interest of UV light to induce the polymerization reaction lies in high polymerization rate, which can be reached under intense illumination, together with the advantage that it can be considered an environmental friendly technique since it is a solvent-free process carried out at room temperature. [8] We have recently investigated the use of photopolymerization technique for IPN formation starting from vinyl ether/acrylate, oxetane/acrylate, [9] or acrylate/epoxy [10] formulations, and we have also studied the use of thermal-UV dual curing process [11] for IPN formation.…”

UV‐Cured Interpenetrating Acrylic‐Epoxy Polymer Networks: Preparation and Characterization

“…[2][3][4][5][6][7] The main advantage of UV light in inducing the polymerization reaction lies in its high polymerization rate, which can be reached under intense illumination, together with the advantage that it can be considered an environmentally-friendly technique, since it is a solventfree process carried out at room temperature. [8] We have recently investigated the use of photopolymerization techniques for IPN formation, starting from vinyl ether/acrylate or oxetane/acrylate formulations [9] and we have also studied the use of the thermal-UV dual-curing process [10] for IPN formation.…”