Poly(arylene ether)s and poly(arylene thioether)s containing the 1,2-dihydro-4-phenyl(2H)- phthalazinone moiety

✍ Scribed by Yong Ding; Antisar R. Hlil; Allan S. Hay

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 136 KB
• Volume: 36
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(199802)36:3<455::aid-pola9>3.0.co;2-q

✦ Synopsis

A series of new high molecular weight poly(arylene ether)s containing the 1,2-dihydro-4-phenyl(2H)phthalazinone moiety have been synthesized. The inherent viscosities of these polymers are in the range of 0.33-0.64 dL/g. They are amorphous and readily soluble in chloroform, DMF, and DMAc. The glass transition temperatures of the polymers range from 241 to 320ЊC and the 5% weight loss temperatures in nitrogen atmosphere range from 473 to 517ЊC. The hydroxy group in the monomer 1,2dihydro-4-(4-hydroxyphenyl)(2H)phthalazin-1-one has been selectively transformed into the N,N-dimethylthiocarbamate group, which was then rearranged to give the S-(N,N-dimethylcarbamate) group via the Newman-Kwart rearrangement reaction. A series of poly(arylene thioether)s containing the 1,2-dihydro-4-phenyl(2H)phthalazinone moiety have also been synthesized via two types of reactions, a N{C coupling reaction and a one-pot reaction between the S-( N,N-dimethylcarbamate) and activated dihalo compounds, in diphenyl sulfone in the presence of a cesium carbonate and calcium carbonate mixture. These poly(arylene thioether)s also have high glass transition temperatures (ranging from 217-303ЊC) and high thermal stabilities. Compared with their poly(ether) analogs, the poly(arylene thioether)s have glass transition temperatures several degrees lower, which is attributed to the more flexible C{S{C bonds.