Synthesis and photooxidation of styrene copolymer bearing camphorquinone pendant groups

Beilstein Journal of Organic Chemistry

Norbert Moszner¹  Branislav Husár²  Ivan Lukáč² 

[1] Ivoclar Vivadent AG, Bendererstrasse 2, FL-9494 Schaan, Liechtenstein;Polymer Institute, Slovak Academy of Sciences, Dúbravská cesta 9, SK-845 41 Bratislava 45, Slovakia;

关键词: camphorquinone;    1,2-diketone;    (±)-10-methacryloyloxycamphorquinone;    photooxidation;    polystyrene;   

DOI  :  10.3762/bjoc.8.37

来源: DOAJ

【 摘 要 】

(±)-10-Methacryloyloxycamphorquinone (MCQ) was synthesized from (±)-10-camphorsulfonic acid either by a known seven-step synthetic route or by a novel, shorter five-step synthetic route. MCQ was copolymerized with styrene (S) and the photochemical behavior of the copolymer MCQ/S was compared with that of a formerly studied copolymer of styrene with monomers containing the benzil (BZ) moiety (another 1,2-dicarbonyl). Irradiation (λ > 380 nm) of aerated films of styrene copolymers with monomers containing the BZ moiety leads to the insertion of two oxygen atoms between the carbonyl groups of BZ and to the formation of benzoyl peroxide (BP) as pendant groups on the polymer backbone. An equivalent irradiation of MCQ/S led mainly to the insertion of only one oxygen atom between the carbonyl groups of camphorquinone (CQ) and to the formation of camphoric anhydride (11) covalently bound to the polymer backbone. While the decomposition of pendant BP groups formed in irradiated films of styrene copolymers with pendant BZ groups leads to crosslinking, only small molecular-weight changes in irradiated MCQ/S were observed.

【 授权许可】

Unknown