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Photochemical reactions of poly(phenyl methacrylate) (PPMA), acetylated poly(hydroxystyrene)(AcPHS) and poly(oxycarbonyloxy-1, 4-phenyleneisopropylidene-1, 4-phenylene) (PC)were investigated by using spectroscopic techniques and by studying the model reactions. When PPMA was exposed to deep UV radiation, it underwent photo-Fries rearrangement, which was confirmed by the appearance of two absorptions assigned to o- and p-hydroxy phenone moieties. The reaction products of phenyl acetate, considered as a model compound of PPMA and AcPHS, were identified by GC as a 2: 1 mixture of o- and p-hydroxyacetophenones. By comparing the changes of the IR spectra of PPMA with those of the model reaction, it was found that the reactivities at the o- and p-positions were almost the same in terms of the rearrangement of PPMA. In addition, the rearrangement tended to saturate as the reaction proceeded. The phenomenon may be ascribed to the photo-shielding effect due to the rearranged structures which have higher absorption coefficients than the PPMA repeating unit. AcPHS also underwent the rearrangement like the other aryl acrylate polymers. PC underwent photo-Fries rearrangement and main chain scission resulting from decarboxylation.<BR>The reaction products of diphenyl carbonate, which was a model compound of PC, were examined using GC-MS in order to investigate the rearranged structures of PC and other structures.206The p1oducts contained phenol and a 26 1 mixture of dihydroxybenzophenone derivatives and hydroxybenzoate derivatives. The results showed that the dihydroxybenzophenone structures were a more likely candidate for the rearranged structures than the hydroxybenzoate structures. The diphenyl carbonate structure is considered to rearrange first to the phenyl hydroxybenzoate structures and subsequently undergo rearrangement to produce the dihydroxybenzophenone structures, since the phenyl hydroxybenzoate structures have much higher ?absorption coefficients than the diphenyl carbonate structure. The phenolic structure seemed to be the most likely ending group resulting from the main chain scission.
- 公益社団法人 日本化学会の論文
公益社団法人 日本化学会 | 論文
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