Direct polycondensation of carboxylic acids and amines catalyzed by 3,4,5-trifluorophenylboronic acid

Macromolecules

Volumn 33, Issue 10, 2000, Pages 3511-3513

  Ishihara, Kazuaki ^a   Ohara, Suguru ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CARBOXYLIC ACIDS; CATALYSTS; COMPOSITION EFFECTS; FLUORINE COMPOUNDS; MOLECULAR WEIGHT; NYLON POLYMERS; ORGANIC SOLVENTS; PLASTIC FILAMENTS; POLYCONDENSATION; POLYIMIDES; THERMAL EFFECTS;

ARAMID; TRIFLUOROPHENYLBORONIC ACID;

AROMATIC POLYMERS;

EID: 0033742916     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma000085o     Document Type: Article

References (9)

1. (a) Sandler, S. R.; Karo, W. Polymer Synthesis, 2nd ed.; Academic Press: San Diego, 1992; Vol. I, Chapter 4.
2. (b) Lenk, R. S. J. Polym. Sci., Macromol. Rev. 1978, 13, 355.
3. (c) Welgos, R. J. Encycl. Polym. Sci. Eng. 1988, 11, 381.
4. Mark, H. F.; Atlas, S. M.; Ogata, N. J. Polym. Sci. 1962, 61, S49.
5. n than the corresponding AB-type and AA+BB-type monomers in noncatalyzed thermal polymerization.
6. Ishihara, K.; Ohara, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 4196.
7. A representative polymerization procedure (method A) is as follows. A flame-dried, 25 mL Schlenk tube equipped with a Teflon-coated magnetic stirring bar and a reflux condenser was charged with carboxylic acids (1 mmol), amines (1 mmol), catalyst 1 (0.01 mmol), NBP (0.4 g), and m-terphenyl (3.6 g). The mixture was heated under a slow argon flow (ca. 20 mL/min) under the conditions indicated in Table 2 and brought to reflux with the removal of water. After the reaction was completed, the resulting mixture was cooled to ambient temperature and diluted with acetone (ca. 30 mL), and the solvents were removed by filtration. The crude solid obtained was washed by heating at reflux in methanol (15 mL) for 1 h, and the solvents were removed by filtration. Washing in methanol was repeated three times. Finally, the desired polyamides were obtained as white or light brown powder by drying under vacuum at 100 °C for 1 h. The filtrate obtained by treatment with acetone was concentrated and purified by flash chromatography on silica gel using hexanes-ethyl acetate (1:1 to 0:1) to recover catalyst 1 as a white solid (ca. 80%).
8. n value of our sample would be expected to be much higher.
9. 9,T = nonamethyleneterephthalamide.