Ring-opening polymerization of various oxirane derivatives using organotin phosphate condensate; Selective synthesis of the polyether containing oxirane ring in the side chain

• Published in: Polymer bulletin (Berlin, Germany) Vol. 61; no. 2; pp. 207 - 216
• Main Authors: Iwasa, Naruhito, Miura, Katsuhito, Kan, Shinji, Furukawa, Yoshiro
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer-Verlag 01.08.2008; Springer
• Subjects: Applied sciences; Characterization and Evaluation of Materials; Chemistry; Chemistry and Materials Science; Complex Fluids and Microfluidics; Exact sciences and technology; Organic Chemistry; Organic polymers; Physical Chemistry; Physicochemistry of polymers; Polymer Sciences; Polymerization; Preparation, kinetics, thermodynamics, mechanism and catalysts; Soft and Granular Matter; Oxirane; High Resolution Mass Spectrometry; Propylene Oxide; Oxirane Ring; Resultant Polymer; Substituent effect; Ring opening polymerization; Molecular structure; Bifunctional compound; Experimental study; Cyclic ether polymer; Propylene oxide polymer; Preparation; Epoxide; Organic phosphate; Tin Organic compounds; Glycidyl ether polymer; Chemical reactivity
• DOI: 10.1007/s00289-008-0949-z
• ISSN: 0170-0839

Ring-opening polymerization (ROP) of various oxirane derivatives of the type, 2,2-R 1 ,R 2 -CCH 2 O [R 1 = H ( 1 ), CH 3 ( 2 ); R 2 = CH 3 ( a ), CH 2 Cl ( b ), CH 2 OCH 3 ( c )], using organotin phosphate (Bu 2 SnO-Bu 3 PO 4 ) condensate has been explored. The ROP of monosubstituted oxiranes ( 1a - c ) afforded ring-opened polymers in high yields ( 1a, 1c = 99% and 1b = 69%); the resultant polymers from monomers 1a and 1b possessed high molecular weights (M n = 9.49 × 10 4 , 10.60 × 10 4 , respectively). In contrast, both polymer yields and molecular weights for resultant polymers in the polymerization of disubstituted oxiranes ( 2a - c ) were considerably lower than those in the polymerization of monosubstituted monomers ( 1a - c ). ROP of glycidyl 2-methylglycidyl ether ( 3 ) possessing two oxirane groups with different reactivity was thus conducted by organotin catalyst; the high molecular weight polyether (M n = 9.17 × 10 4 ) containing oxirane ring in the side chain has successfully been obtained in moderate yield.