Polyterephthalamides with naphthoxy-pendent groups

A series of new aromatic polyamides having pendent naphthoxy groups were synthesized by the triphenyl phosphite-activated polycondensation of (2-naphthoxy)terephthalic acid (NOTPA) with various aromatic diamines in a medium consisting of N-methyl-2-pyrrolidone (NMP), pyridine, and calcium chloride. The diacid monomer NOTPA was prepared from the nitro displacement of dimethyl 2-nitroterephthalate with the potassium naphthoxide of β-naphthol, followed by base-induced ester hydrolysis. All the resulting polymers were noncrystalline and readily soluble in aprotic polar solvents such as NMP and N,N-dimethylacetamide. Almost all the polymers could be solution-cast to tough, creasable amorphous films with good mechanical properties, the values of tensile strengths ranging from 90 to 124 MPa with initial moduli ranging from 1.72 to 2.51 GPa. Except for two examples, all the other polyamides displayed discernible glass transitions between 189 and 248 °C in the differential scanning calorimetric traces. These polyamides showed insignificant decomposition below 400 °C in nitrogen or air. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 1781–1789, 2002

[1]  Á. Lozano,et al.  Synthesis and characterization of new soluble Aromatic polyamides derived from 1,4-bis(4-carboxyphenoxy)-2, 5-di-tert-butylbenzene , 2001 .

[2]  S. Hsiao,et al.  Polyamides based on diamines containing aryloxy groups: Structure-property relationships , 2000 .

[3]  Á. Lozano,et al.  Synthesis and characterization of new soluble aromatic polyamides based on 4‐(1‐adamantyl)‐1, 3‐bis(4‐aminophenoxy)benzene , 2000 .

[4]  S. Hsiao,et al.  Synthesis and characterization of aromatic polyamides based on a bis(ether‐carboxylic acid) or a dietheramine derived from tert‐butylhydroquinone , 1999 .

[5]  G. Eastmond,et al.  1,2-bis(carboxyphenoxy)arylenes and aramids and polyarylates therefrom : synthesis and properties , 1999 .

[6]  L. Mathias,et al.  Synthesis and Characterization of Aromatic Polyamide and Polyimides from Trimethyl- and Di-t-butylhydroquinone Based Ether Linked Diamines , 1998 .

[7]  J. Mikroyannidis,et al.  Aromatic polyamides and polyimides bearing bulky ether pendent groups derived from 1-aryloxy-2,4-diaminobenzenes , 1996 .

[8]  K. Winey,et al.  Melt intercalation of polystyrene in layered silicates , 1996 .

[9]  M. Lewandowski,et al.  Synthesis of silylene-vinylene oligomers via catalytic polycondensation of divinyldimethylsilane , 1996 .

[10]  M. Kakimoto,et al.  Preparation and properties of aromatic polyimides from 2,2′‐bis(p‐aminophenoxy)biphenyl or 2,2′‐bis)p‐aminophenoxy)‐1,1′‐binaphthyl and aromatic tetracarboxylic dianhydrides , 1993 .

[11]  Á. Lozano,et al.  Polyisophthalamides with phenylthio pendent groups , 1992 .

[12]  H. Yang.  Aromatic High-Strength Fibers , 1989 .

[13]  H. Kricheldorf,et al.  New polymer syntheses, 37. Glassy, nematic copolyesters from aryloxyterephthalic acids, hydroquinone and 4‐hydroxybenzoic acid , 1989 .

[14]  H. Kricheldorf,et al.  New polymer syntheses, 35. Thermotropic (co)polyesters of phenoxyterephthalic acid , 1989 .

[15]  J. D. Abajo,et al.  Polyisophthalamides with phenoxy pendant groups , 1988 .

[16]  V. Döring,et al.  New polymer syntheses, 30. Thermotropic polyesters of 2‐(2‐naphthylthio)terephthalic acid , 1988 .

[17]  V. Döring,et al.  New polymer syntheses, 29. Thermotropic (co)polyesters of 2‐phenylthioterephthalic acid and various diphenols , 1988 .

[18]  M. Kakimoto,et al.  Preparation and properties of polyamides from 4‐phenoxy‐ and 4‐phenylthio‐m‐phenylenediamine and both aromatic and aliphatic diacids , 1988 .

[19]  L. F. Beste,et al.  Structure of Poly(1,4-benzamide) Solutions , 1977 .

[20]  P. Morgan,et al.  Poly(1,4-phenyleneterephthalamides). Polymerization and Novel Liquid-Crystalline Solutions , 1977 .

[21]  M. Matsumoto,et al.  Studies on reactions of the N‐phosphonium salts of pyridines. XIV. Wholly aromatic polyamides by the direct polycondensation reaction by using phosphites in the presence of metal salts , 1975 .