화학공학소재연구정보센터
Reactive & Functional Polymers, Vol.26, No.1, 145-155, 1995
Polymer-supported reagents as aids in controlled degradation of polymers containing ozonides in the main chain to give telechelic oligomers
The work-up of ozonides derived from the ozonolysis of methacrylate copolymers containing main chain unsaturation has been studied. We have used: periodate supported on Amberlyst A26 (SPIR) (a supported oxidizing agent); polystyrene-supported diphenyl phosphine (SPR) (a mild supported reducing agent) and borohydride supported on Amberlyst A26 (EER) (a more powerful supported reducing agent). Poly(butyl methacrylate-cobutadiene)s were synthesized by starve fed emulsion polymerization. These materials, and the homopolymer, poly(butyl methacrylate), were then ozonized at different temperatures and worked up with each of the reagents listed above. The differing work-ups generated telechelic oligomers in good yield (99%+). Changes in molecular weight with ozonization temperature were observed. Aldehyde end-groups were detected by H-1- and C-13-NMR. Hydroxyl end-groups were observed by FTIR and C-13-NMR spectroscopy. The presence of hydroxyl groups was also further confirmed by forming the tosylate. Carboxyl groups were observed by FTIR and C-13-NMR and quantified by titration. SPR-generated oligomers had approximately 80% of the chain-ends aldehyde functional, EER and SPIR gave oligomers with 99+% hydroxyl and carboxyl functionality, respectively.