A novel synthesis of polyethers with pendant hydroxyl groups by polyaddition of bis(oxetane)s with bis(phenol)s

✍ Scribed by Tadatomi Nishikubo; Atsushi Kameyama; Muneharu Ito; Tomoe Nakajima; Haruo Miyazaki

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 167 KB
• Volume: 37
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(19990801)37:15<2781::aid-pola12>3.0.co;2-3

✦ Synopsis

The polyaddition of 1,4-bis [(3-ethyl-3-oxetanyl)methoxymethyl]benzene (BEOB) with 3,3Ј,5,5Ј-tetrachlorobisphenol A (TCBPA) was examined with or without catalysts. High molecular weight polymer (polymers 1) (M n ϭ 13,600) with pendant primary hydroxyl groups was obtained in a 99% yield without any gel products when the reaction was performed with 5 mol % of tetraphenylphosphonium bromide as a catalyst in NMP at 160°C for 96 h. However, when the reaction was carried out without a catalyst under the same conditions, a low molecular weight polymer (M n ϭ 3200) was obtained in a 51% yield. The structure of the resulting polymer was confirmed by IR, 1 H-NMR, and 13 C-NMR spectra. In this reaction system, it was also found that tetraphenylphosphonium iodide and crown ether complexes such as 18-crown-6 (18-C-6)/ KBr and 18-C-6/KI have high catalytic activity. Polyadditions of 1,4-bis [(3-methyl-3oxetanyl)methoxymethyl]benzene with TCBPA and BEOB with 3,3Ј,5,5Ј-tetrabromobisphenol-S were also examined, and corresponding polymers (polymers 2 and 3) were obtained in good yields.