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Abstract

The polyimides containing the hydroxy group were synthesized from 3,3^'-dihydroxybenzidine (I) and previously prepared tetracarboxylic dianhydrides, 3,3^''',4,4^'''-p-quaterphenyltetracarboxylic dianhydride (IId), 3,3^'''',4,4^''''-p-quinquephenyltetracarboxylic dianhydride (IIe) and 3,3^''''',4,4^'''''-p-sexiphenyltetracarboxylic dianhydride (IIf), and the properties were compared with those of corresponding polyimides from commercially available dianhydrides. The polyimides were synthesized by the conventional two-step procedure of ring-opening polyaddition in N-methyl-2-pyrrolidinone (NMP) and subsequent thermal cyclic dehydration. All the polyimides were soluble in NMP on heating. The glass transition temperature (T _g) of the polyimides ranged from 336—360^°C, and were not dependent on the structure of tetracarboxylic dianhydride. The storage modulus of some polyimides did not decrease at high temperature. All the polyimides underwent thermal conversion to polybenzoxazoles upon heating to 500^°C for 1 h under vacuum. The thermal conversion of the polyimides to polybenzoxazoles was confirmed by Fourier transform infrared spectrometry. The 10% weight loss temperature (T ₁₀) of the polybenzoxazoles was 530—700^°C in nitrogen, and the polybenzoxazoles were thermally stable. In particular, the T ₁₀ values of the polybenzoxazoles from IId, IIe, and IIf were above 630^°C.

Keywords

3,3'-dihydroxybenzidine tetracarboxylic dianhydrides polyimides containing hydroxy group polybenzoxazoles

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References

Morikawa, A. (2000). Synthesis and Characterization of Novel Aromatic Polyimides from Aromatic Diamine and 3,3''' , 4,4'''-p-Quaterphenyltetracarboxylic Dianhydride, Polym. J., 32: 275—279.

Morikawa, A. and , Hosoya, Y. (2002). Synthesis and Characterization of Novel Aromatic Polyimides from Aromatic Diamine and 3,3'''', 4,4''''-p-Quinquephenyltetracarboxylic Dianhydride, Polym. J., 34: 544—549.

Morikawa, A. and Ono, K. (2000). Synthesis and Characterization of Novel Aromatic Polyimides from Aromatic Diamine and 3,3''''' , 4,4'''''-p-Sexiphenyltetracarboxylic Dianhydride, Polym. J., 32: 948—953.

Morikawa, A. and Ono, K. (2001). Aromatic polyimides containing p-quaterphenyl and p-sexiphenyl units, High. Perform. Polym ., 13: S73—S83.

Imai, Y. (1995). Synthesis of novel organic-soluble high-temperature aromatic polymers, High. Perform. Polym., 7: 337—345.

Jeong, H.-J. , Ohishi Y. , Kakimoto, M. and Imai, Y. (1994). Synthesis and Characterization of Novel Aromatic Polyimides from 3, 4-Bis(4-aminophenyl)-2,5-diphenylthiophene and Aromatic Tetracarboxylic Dianhydrides, Polym. J., 26: 373—377.

Jeong, H.-J. , Ohishi, Y. , Kakimoto, M. and Imai, Y. (1991). Synthesis and characterization of new soluble aromatic polyimides from 3,4-bis (4-aminophenyl)-2,5-diphenylfuran and aromatic tetracarboxylic dianhydrides, J. Polym. Sci., Polymer. Chem. Ed., 29: 39—43.

Jeong, H.-J. , Kakimoto, M. and Imai, Y. (1991). Synthesis and characterization of new soluble aromatic polyimides from 3,4-bis(4-aminophenyl)-2,5-diphenylpyrrole and aromatic tetracarboxylic dianhydrides, J. Polym. Sci., Polymer. Chem. Ed., 29: 1691—1695.

Ohishi, Y. , Ishida, M. , Kakimoto, M. , Imai, Y. and Kurosaki, T. (1991). Preparation and properties of novel soluble aromatic polyimides from 4,4'-diaminotriphenylamine and aromatic tetracarboxylic dianhydrides, J. Polym. Sci., Polymer. Chem. Ed., 30: 1027—1035.

10.

Spiliopoulos, I.K. and Mikroyannidis , J.A. (1998). Soluble Phenyl- or Alkoxyphenyl-Substituted Rigid-Rod Polyamides and Polyimides Containing m-Terphenyls in Main Chain, Macromolecules, 31: 1236— 1245.

11.

Spiliopoulos, I.K. and Mikroyannidis , J.A. (1998). Synthesis of Soluble, Blue-Light-Emitting Rigid-Rod Polyamides and Polyimides Prepared from 2',6',3''',5'''-Tetraphenyl- or Tetra(4-biphenyl)-4,4''''-diaminop-quinquephenyl, Macromolecules, 31: 515—521.

12.

Morikawa, A. and Hatakeyama, T. (1999). Synthesis and Characterization of Novel Aromatic Polyimides from 1,4-Bis(4-aminophenyl)-2,3-diphenylnaphtharene and Aromatic Tetracarboxylic Dianhydrides, Polym. J., 31: 76—78.

13.

Morikawa, A. , Furukawa, T. and Moriyama, Y. (2005). Synthesis and Characterization of Novel Aromatic Polyimides from Bis(4-amino-2-biphenyl)ether and Aromatic Tetracarboxylic Dianhydrides, Polym. J., 37: 759—766.

14.

Morikawa, A. , Furukawa, T. and Moriyama, Y. (2006). Synthesis and Characterization of Novel Aromatic Polyimides from Bis(4-amino-2-biphenyl)ether and Aromatic Tetracarboxylic Dianhydrides, High. Perform. Polym., 18: 593—602.

15.

Bes, L. , Rousseau, A. , Boutevin, B. , Mercier, R. , Sillion, B. and Toussaere, E.M. (2000). Synthesis and Characterization of Aromatic Polyimides Bearing Nonlinear Optical Chromophores, High. Perform . Polym., 12: 169—176.

16.

Akimoto, S. , Jikei, M. and Kakimoto, M. (2000). A Novel Photosensitive Polyimide: a Polyimide Containing the Hydroxytriphenylamine Structure with Diazonaphthoquinone, High. Perform. Polym., 12: 177—184.

17.

Schab-Balcerzak, E. and Sek, D. (2001). New Soluble Polyimides Containing Hydroxylic Groups: I. Synthesis and characterization, High. Perform . Polym., 13: 45—53.

18.

Schab-Balcerzak, E. , Jikei, M. and Kakimoto, M. (2003). Thermal Rearrangement of Poly(o-hydroxyimide)s Synthesized from 4,6-Diaminoresorcinol Dihydrochloride , Polym. J., 35: 208—212.

19.

Gordon, L. , Powers, J.M. , Jeskey, S.J. and Mathias, L.J. (1999). Thermal Conversion of Hydroxy-Containing Imides to Benzoxazoles: Polmer and Model Compound Study , Macromolecules, 32: 3598— 3612.

Synthesis of Polyimides from 3,3'-dihydroxybenzidine and Conversion to Polybenzoxazoles

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