Polyimides Containing Trans-1,4-cyclohexane Unit. Polymerizability of their Precursors and Low-CTE,Low-K and High-Tg Properties

Abstract

The structure-polymerizability relationship has been investigated in a series of polyimide (PI) precursor, poly(amic acid) systems obtained from trans-1,4-cyclohexanediamine (CHDA) and various dianhydrides. The results have shown that the systems examined in this work can be classified into three groups on the basis of the solubility of the salt formed at the initial reaction stage: (A) polymerization proceeds at room temperature via gradual salt dissolution; (B) polymerization is initiated upon heating at an appropriate temperature; (C) no reaction takes place under any conditions owing to the formation of completely insoluble salt. The polymerizability based on the salt solubility in each system was considered from the points of view of the strength of acid in an initially formed low-molecular weight amic acid and their steric structures. In order to improve the non-polymerizability in the systems of group C, sequencecontrolled copolymerization was carried out using a rod-like fluorinated diamine as a comonomer and this resulted in high-molecular weight CHDA-containing copoly(amic acid)s. The properties of a series of CHDA-based PIs have also been investigated. Some of them simultaneously achieved a low coefficient of thermal expansion (CTE), a low dielectric constant (K), a high glass transition temperature (T₉) and good film flexibility The structure-property relationship indicates the molecular-design of low-K and low-CTE PI materials.

Keywords

Cycloaliphatic polyimides dielectric constant coefficient of thermal expansion trans-1,4-cyclo-hexanediamine

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References

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

[2] Bessonov M I , Koton M M , Kudryavtsev V V and Laius L A (eds) 1987 Polyimide: Thermally Stable Polymers (New York: Plenum)

[3] Feger C , Khojasteh M M and McGrath J E (eds) 1989 Polyinides. Materials, Chemistry and Characterization (Amsterdam: Elsevier)

[4] Feger C , Khojasteh M M and Htoo M S (eds) 1993 Advances in Polyimide Science and Technology (Lancaster: Technomic)

[5] Bessonov M I and Zubkov V A (eds) 1993 Polyamic Acid and Polyimides. Synthesis, Transformation and Structure (Boca Raton, FL: CRC Press)

[6] Ghosh M K and Mittal K L (eds) 1996 Polyimides: Fundamentals and Applications (New York: Marcel Dekker)

[7] Feger C , Khojasteh M M and Molis S E (eds) 1996 Polyimides: Trends in Materials and Applications (New York: Society of Plastic Engineers)

[8] Sachdev H S , Khojasteh M M and Feger C (eds) 1999 Advances in Polyimides and Low Dielectric Polymers (New York: Society of Plastic Engineers)

[9] Mittal K L (ed) Polyimides and Other High Temperature Polymers: Synthesis, Characterization and Applications vol 1 (Zeist, The Netherlands: VSP)

10.

[10] Imai Y and Yokota R (eds) 2002 The Latest Polyimnides: Fundamentals and Applications (Tokyo: NTS) (in Japanese)

11.

[1ll Numata S Oohara S , Fujisaki K , Imaizumi K and Kinjyo N 1986 J. Appl. Polym. Sci. 31 101-101

12.

[12] Numata S , Fujisaki K and Kinjyo N 1987 Polymer 28 2282-2282

13.

[13] Hasegawa M , Matano T , Shindo Y and Sugimura T 1996 Macromolecules 29 7897-7897

14.

[14] Coburn J C and Pottiger M T 1996 Polyimides: Fundamentals and Applications eds M K Ghosh and K L Mittal (New York: Marcel Dekker) p 207-207

15.

[15] Hasegawa M 2001 Polyin. Prepr Jpn. 50 858-858

16.

[16] Goto K 2002 The Latest Polyimides. Fundamentals and Applications eds Y Imai and R Yokota (Tokyo: NTS) p 270-270 (in Japanese)

17.

[17] Matsuura T , Hasuda Y Nishi S and Yamada N 1991 Macromolecules 24 5001-5001

18.

[18] Matsumoto T 1999 Macromolecules 32 4933-4933

19.

[19] Goto K , Inoue Y and Matsubara M 2001 J. Photopolym. Sci. Technol. 14 33-33

20.

[20] Feiring A E , Auman B C and Wonchoba E R 1993 Macromolecules 26 2779-2779

21.

[21] Hasegawa M 2001 High Petform. Polym. 13 S93-S93

22.

[22] Manhaecht B , Rimez B , Willem R , Biesemans M and Koning C E 2002 J. Polym. Sci. A 40 1962-1962

23.

[23] Volksen W , Cha H J , Sanchez M I and Yoon D Y 1996 Reactive Functional Polym. 30 61-61

24.

[24] Imai Y Nemoto H and Kakimoto M 1996 J. Polym. Sci. A 34 701-701

25.

[25] Hasegawa M , Shindo Y Sugimura T , Ohshima S , Horie K , Kochi M , Yokota R and Mita I 1993 J. Polym. Sci. B31 1617-1617

26.

[26] Hasegawa M , Sensui N , Shindo Y and Yokota R 1999 Macmmolecules 32 387-387

27.

[27] Huang H W , Kaneko T I , Horie K and Watanabe J 1999 Polymer 40 3821-3821

28.

[28] Hasegawa M , Uchida A and Manami H 2001 Polym. Prepr Jpn. 50 1767-1767

29.

[29] Ando S and Matsuura T 2002 The Latest Polyimides. Fundamentals and Applications eds Y Imai and R Yokota (Tokyo: NTS) p 292-292 (in Japanese)

30.

[30] Hasegawa M and Horie K 2001 Prog. Polym. Sci. 26 259-259

31.

[31] Hasegawa M , Sensui N , Shindo Y and Yokota R 1999 J Polym. Sci. B 37 2499-2499

32.

[32] Vladimirov L , Hasegawa M Yokota R and Kochi M 1999 Advances in Polyimides and Low Dielectric Polymers eds H S Sachdev , M M Khojasteh and C Feger C (New York: Society of Plastic Engineers) p 185-185

33.

[33] Kikuchi T and Saito T 1988 Kagaku (Chemistry) 43 668-668 (in Japanese)

34.

[34] Morikawa A and Ono K 2001 High Perform. Polym. 13 S73-S73

35.

[35] Suzuki H , Abe T , Takaishi K , Narita M and Hamada F 2000 J Polym. Sci. A 38 108-108