Synthesis and characterization of fluorinated poly(aryl ether ketone)s containing 1,4-naphthalene moieties

✍ Scribed by Frank W. Mercer; Matilda M. Fone; Martin T. McKenzie

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 695 KB
• Volume: 35
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(199702)35:3<521::aid-pola16>3.0.co;2-q

✦ Synopsis

The new monomer 2,2-bis[4-(4-{4-fluorobenzoyl }-1 -naphthoxy)pheny l]hexafluoropropane (2) was synthesized in a two-step reaction sequence. 2,2-his[4-( 1-naphthoxy)pheny l]hexafluoropropane (1) was prepared using the Ullmann ether synthesis reaction of 4,4-(hexafluoroisopropylidiene )diphenol with 1-hromonaphthalene. Friedel-Crafts acylation of 1 with 4-fluorobenzoyl chloride in methylene chloride containing dimethylsulfone selectively afforded 2 in 82% yield. The polycondensation of 2 with various hisphenols in DMAc in the presence of an excess of potassium carbonate as a condensation reagent was carried out at 165°C to quantitatively afford the corresponding fluorinated poly(aryl ether ketone)s containing 1,4naphthalene moieties. Thermal analysis of the polymers showed them to have Trs ranging from 194 to 230"C and to be thermally stable in air up with initial weight losses at about 5000C. In addition, these novel polymers exhibited excellent volubility in organic solvents including NMP, DMAc, and chloroform. ~1%7 .John W'iley & Sons, In(,.