Processable Poly(Keto-Imide)s Having Bulky Pendent Ether Groups

Abstract

1, 3-Bis(3-aminobenzoyl)benzene (BAB), 1, 3-bis(3-amino-4-phenoxybenzoyl)benzene (BAPB) and 1, 3-bis(3-amino-4-biphenoxybenzoyl)benzene (BABB) were synthesized from 1, 3-bis(3-nitro-4-chlorobenzoyl)benzene. By using these three diamines and commercially available tetracarboxylic dianhydrides such as 3, 3′, 4, 4′-benzophenone tetracarboxylic dianhydride (BTDA) and pyromellitic dianhydride (PMDA), several kinds of poly(keto-imide)s were synthesized. Thermal properties and processability such as melt-flowability and solubility in organic solvents of the obtained poly(keto-imide)s were investigated by focusing on the chemical structures of their repeating structure units. Inherent viscosities of poly(keto-imide)s ranged from 0.54 to 0.75 dl g⁻¹. These poly(keto-imide)s displayed glass transition temperatures (T _g) between 219 and 256 °C, and only the poly(keto-imide) prepared from BAB and PMDA showed a melting point (T _m)at 451 °C. Melt-flowabilities of these poly(keto-imide)s except for BAB/PMDA poly(keto-imide) were observed between 285 and 330 °C. The poly(keto-imide)s having bulky pendent ether groups were soluble in chloroform, 1, 1, 2-trichloroethane, N, N-dimethylacetamide and m-cresol at ambient temperature.

Get full access to this article

View all access options for this article.

References

[1] Mittal K L (ed) 1984 Polyimides: Synthesis, Characterization, Application (New York: Plenum)

[2] Critchley J P and White M A 1972 J. Polym. Sci.: Polym. Chem. 10 1809-1809

[3] Harris F W and Lanier L H 1977 Structure–Solubility Relationships in Polymers ed F W Harris and R B Seymour (New York: Academic) p 183-183

[4] Kumar D J 1984 Polym. Sci.: Polym. Chem. 20 3439-3439

[5] Harris F W , Hsu S L C and Tso C C 1990 Polym. Preprints (Am. Chem. Soc., Div. Polym. Chem.) 31 324-324

[6] Spiliopoulos I K and Mikroyannidis J A 1996 Polymer 37 3331-3331

[7] Harris F W , Lin S-H , Li F and Cheng S Z D 1996 Polymer 37 5049-5049

[8] Yamaguchi A and Ohta M 1986 Int. SAMPE, Tech. Conf. Ser. 18 229-229

[9] Takekoshi T , Webb J L , Anderson P P and Olsen C E 1988 IUPAC 32nd Int. Symp. on Macromolecules (Kyoto) abstract, p 464-464

10.

[10] AURUM™ (Mitsui Toatsu Chemicals, Inc.)

11.

[11] Tamai S , Yamashita W and Yamaguchi A 1994 Int. SAMPE, Tech. Conf. Ser. 26 365-365

12.

[12] Tamai S , Ookawa Y and Yamaguchi A 1995 40th Int. SAMPE Symp. 40 1412-1412

13.

[13] Tamai S , Yamaguchi A and Ohta M 1996 Polymer 37 3683-3683

14.

[14] Tamai S , Ohkawa Y and Yamaguchi A 1997 Polymer 38 4079-4079

15.

[15] Tamai S , Oikawa H , Ohta M and Yamaguchi A Polymer at press

16.

[16] Progar D J , St Clair T L , Burks H , Gautreavx C , Yamaguchi A and Ohta M 1989 Int. SAMPE, Tech. Conf. Ser. 21 1 544-544

17.

[17] Ohta M , Tamai S , Towell T W , Johnston N J and St Clair T L 1990 Int. SAMPE; Symp. 35 1 1030-1030

18.

[18] St Clair T L 1989 Polymer Sci. 29 63-63

19.

[19] Hergenrother P M , Wakelyn N T and Havens S J 1987 J. Polym. Sci. 25 1093-1093

20.

[20] Hergenrother P M and Havens S J 1989 J. Polym. Sci. 27 1161-1161

21.

[21] St Clair T L and St Clair A K 1977 J. Polym. Sci., Polym. Chem. 15 1529-1529

22.

[22] Hergenrother P M 1989 SPE Conf. on High Temperature Polymers and their Uses (Cleveland, OH, 2–4 October 1989)

23.

[23] Christopher M D 1969 Chem. Abstracts 70 68-68 (116221X)