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Study of photopolymers. XXX. Syntheses of new di(meth) acrylate oligomers by addition reactions of epoxy compounds with active esters

1987; Wiley; Volume: 25; Issue: 11 Linguagem: Inglês

10.1002/pola.1987.080251110

1099-0518

Tadatomi Nishikubo, Eiji Takehara, Seiji Saita, Takahisa Matsumura,

Synthesis and properties of polymers

Abstract Some dimethacrylate oligomers were synthesized by new addition reactions of 2,2‐(4‐hydroxyphenyl)propane diglycidyl ether (BPGE) or glycidyl methacrylate (GMA) with phenyl methacrylates such as phenyl methacrylate (PMA), 4‐nitrophenyl methacrylate (NPMA), 2,4‐dichlorophenyl methacrylate (DCPMA), 4‐methoxyphenyl methacrylate (MPMA), and (4‐cinnamoyloxy)phenyl methacrylate (CIPMA) using tetrabutylammonium bromide as a catalyst at 120°C. The other new dimethacrylate or diacrylate oligomers were also prepared by the addition reactions of GMA or glycidyl acrylate with active esters such as di(S‐phenyl)thioisophthalate (PTIP), di(4‐nitrophenyl)isophthalate (NPIP), di(4‐nitrophenyl)adipate (NPAD), and di(4‐nitrophenyl)sebacate (NPSB) under similar reaction conditions. Furthermore, the rates of photochemical reaction of the obtained dimethacrylate oligomers were measured with 3 mol % of various photosensitizers such as benzoin iso ‐propyl ether (BIPE), 2‐ethylanthraquinone (EAQ), and benzophenone (BP). The rate of photochemical reaction of BPGE‐DCPMA oligomer was higher than those of BPGE‐PMA, BPGE‐NPMA, and BPGE‐MPMA oligomers using BIPE as a photosensitizer. However, the photochemical reactivity of the unsensitized BPGE‐CIPMA was almost the same as that of the sensitized BPGE‐DCPMA. On the other hand, when EAQ was used as a photosensitizer, GMA‐PTIP oligomer showed much higher reactivity than GMA‐NPAD, GMA‐NPSB, and GMA‐NPIP oligomers. Also it was shown that the activity of EAQ as a sensitizer was higher than BIPE and BP in the photochemical reaction of BPGE‐DCPMA oligomer.