Chemistry and Properties of Imide Oligomers from Phenylethynyl-Containing Diamines

Abstract

As an extension of work on pendent phenylethynyl-containing imide oligomers, three new diamines containing pendent phenylethynyl groups were prepared and characterized. These diamines were used to prepare pendent and pendent and terminal phenylethynyl imide oligomers via the amide acid route in N-methyl-2-pyrrolidinone at a calculated number average molecular weight of 5000 g mol⁻¹. The pendent phenylethynyl groups were randomly distributed along the oligomer backbone and provided a means of controlling the distance between reactive sites. The imide oligomers were characterized and thermally cured, and the cured polymers evaluated as thin films and compared with materials of similar composition prepared from 3,5-diamino-4′-phenylethynylbenzophenone. This work was performed as part of a continuing research effort to develop structural resins for potential aeronautical applications.

Get full access to this article

View all access options for this article.

References

[1] Harris F W , Padaki S M and Vavaprath S 1980 Polym. Prepr. 21 3-3

[2] Harris F W , Pamidimukkala A , Gupta R , Das S , Wu T and Mock G 1993 Polym. Prepr. 24 324-324

Harris F W , Pamidimukkala A , Gupta R , Das S , Wu T and Mock G 1984 J. Macromol. Sci.-Chem. A21 1117-1117

[3] Harris F W , Sridhav K and Das S 1984 Polym. Prepr. 25 110-110

[4] Hino S, Sato S and Suzuki O 1988 Japan. Kokai Tokkyo Koho (Japanese Patent) 63196564

Hino S , Sata S and Suzuki O 1989 Chem. Abstr. 110 115573w-115573w

[5] Paul C W , Schultz R A and Fenelli S P 1993 Advances in Polyimide Science and Technology ed C Feger , M M Khoyasteh and M S Htoo (Lancaster, PA: Technomic) p 220-220

[6] Jensen B J , Hergenrother P M and Nwokogu G 1992 Polym. Prepr. 33 914-914

Jensen B J , Hergenrother P M and Nwokogu G 1993 Polymer 34 630-630

10.

[7] Byrant R G , Jensen B J and Hergenrother P M 1993 Polym. Prepr. 34 566-566

11.

[8] Meyer G W , Jayaraman S and McGrath J E 1993 Polym. Prepr. 34 540-540

12.

[9] Jayaraman S , Meyer G , Moy T M , Srinivasan R and McGrath J E 1993 Polym. Prepr. 34 513-513

13.

[10] Havens S J , Bryant R G , Jensen B J and Hergenrother P M 1994 Polym. Prepr. 35 553-553

14.

Havens S J , Bryant R G , Jensen B J and Hergenrother P M 1994 J. Polym. Sci., Pt. A.: Polym. Chem. 32 304-304

15.

[11] Jensen B J , Bryant R G and Wilkinson S P 1994 Polym. Prepr. 35 539-539

16.

[12] Bryant R G , Jensen B J , Smith JG Jr and Hergenrother P M 1994 Sci. Adv. Mater. Proc. Eng. Ser. 39 273-273

17.

[13] Hergenrother P M , Bryant R G , Jensen B J , Smith JG Jr and Wilkinson S P 1994 Adv. Mater. Proc. Eng. Ser. 39 961-961

18.

[14] Smith J G Jr and Hergenrother P M 1994 Polym. Prepr. 35 353-353

19.

Smith J G Jr and Hergenrother P M 1994 Polymer 35 4857-4857

20.

[15] Johnston J A , Li F M , Harris F W and Takekoshi T 1994 Polymer 35 4865-4865

21.

[16] Takekoshi T and Terry J M 1994 Polymer 35 4874-4874

22.

[17] Meyer G W , Glass T E , Grubbs H J and McGrath J E 1994 Polym. Prepr. 35 549-549

23.

Meyer G W , Glass T E , Grubbs H J and McGrath J E 1995 J. Polym. Sci.: Pt. A: Polym. Chem. 33 2141-2141

24.

[18] Meyer G W , Lee Y J , Pak S J and McGrath J E 1994 Polym. Mater. Sci. Eng. Prepr. 70 496-496

25.

[19] Hergenrother P M and Jensen B J 1994 US Patent 5344982

26.

[20] Hergenrother P M, Bryant R G, Jensen B J and Havens S J 1995 US Patent 5412066

27.

[21] Connell J W , Smith JG Jr , Cano R J and Hergenrother P M 1996 SAMPE 41 1102-1102

28.

[22] Hou T H , Jensen B J and Hergenrother P M 1996 J. Composite Mater. 30 109-109

29.

[23] Connell J W , Smith JG Jr and Hergenrother P M 1997 High Perform. Polym. 9 309-309

30.

[24] Smith J G Jr , Connell J W and Hergenrother P M 1997 Polymer 38 4657-4657

31.

[25] Connell J W , Smith J G Jr and Hergenrother P M 1997 Int. SAMPE Tech. Conf. Ser. 29 317-317

32.

[26] Hergenrother P M and Rommell M 1996 SAMPE 41 1061-1061

33.

[27] Rommell M , Konopka L and Hergenrother P M 1996 Int. SAMPE Tech. Conf. Ser. 28 14-14

34.

[28] Connell J W , Smith JG Jr and Hergenrother P M 1998 High Perform. Polym. 10 273-273

35.

[29] Austin W B , Bilow N , Kelleghan W J and Lau K S Y 1981 J. Org. Chem. 46 2280-2280