Thermosetting resin composition

• US 5,576,398 A
• Filed: 11/21/1995
• Issued: 11/19/1996
• Est. Priority Date: 07/07/1995
• Status: Expired due to Term

• Current Assignee: JSR Corporation
• Original Assignee: Japan Synthetic Rubber Co., Ltd.
• Inventors: Kawaguchi, Kazuo, Komatsu, Hiromi, Fujiwara, Shuetsu, Takahashi, Masayuki
• Primary Examiner(s): Marquis, Melvyn I.
• Assistant Examiner(s): GULAKOWSKI, RANDY P
• Application Number:
  US08/561,626
• Time in Patent Office: 364 Days
• Field of Search: 525/423, 525/430, 525/452, 525/453, 525/454, 525/504, 525/528, 525/533, 525/540, 525/907, 528/45, 528/48, 528/65, 528/73, 528/93, 528/312, 528/322
• US Class Current: 525/528
• CPC Class Codes: C08G 18/095 oligomerisation to carbodiimide or uretone-imine groups
• CPC Class Codes: C08G 18/345 having three carboxylic acid groups
• CPC Class Codes: C08L 2666/20 Macromolecular compounds having nitrogen in the main chain according to C08L75/00 - C08L79/00; Derivatives thereof
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: Y10S 525/907 Polycarbodiimide

Abstract

A thermosetting resin composition which comprises (A) a resin in which at least one compound having a graft-reactive group such as a carboxyl group, a primary amino group or a secondary amino group and a carboxylic anhydride group has been grafted on a polycarbodiimide and (B) an epoxy compound. The said thermosetting resin composition retains heat resistance, electrically insulating properties and mechanical properties characteristic of polycarbodiimide, is excellent in solubility in various solvents and storage stability in the form of a solution and can be easily cured under mild conditions, and can produce a cured product excellent in humidity resistance, transparency, chemical stability and adhesiveness to various substrates.

Claims

1. A thermosetting resin composition which comprises:

(A) a resin in which at least one compound having a graft-reactive group and a carboxylic anhydride group has been grafted on a polycarbodiimide having a repeating unit represented by the general formula (1);

space="preserve" listing-type="equation">--N═

C═

N--R.sup.1 -- (1)

wherein R¹ represents a divalent organic group, and

(B) an epoxy compound.

2. The thermosetting resin composition according to claim 1, wherein the polycarbodiimide is one obtained by reacting an organic polyisocyanate in the presence of a catalyst which accelerates the carbodiimidization of the isocyanate group.

3. The thermosetting resin composition according to claim 2, wherein the organic polyisocyanate is at least one organic diisocyanate.

4. The thermosetting resin composition according to claim 3, wherein the organic diisocyanate is an isocyanate prepolymer having isocyanate groups at both ends.

5. The thermosetting resin composition according to claim 1, wherein the polycarbodiimide has a polystyrene-reduced number average molecular weight Mn of 400 to 500,000 as determined by a gel permeation chromatography.

6. The thermosetting resin composition according to claim 1, wherein the compound having a graft-reactive group and a carboxylic anhydride group is a compound which reacts with the polycarbodiimide through the graft-reactive group.

7. The thermosetting resin composition according to claim 1, wherein the graft-reactive group is a functional group having an active hydrogen atom.

8. The thermosetting resin composition according to claim 1, wherein the graft-reactive group is selected from the group consisting of a carboxyl group, a primary amino group and a secondary amino group.

9. The thermosetting resin composition according to claim 1, wherein the compound having a graft-reactive group and a carboxylic anhydride group is at least one member selected from the group consisting of aromatic tricarboxylic anhydrides, monoalkyl esters of aromatic tetracarboxylic monoanhydrides, aliphatic tricarboxylic anhydrides, aminoaromatic dicarboxylic anhydrides and aminoaliphatic dicarboxylic anhydrides.

10. The thermosetting resin composition according to claim 1, wherein the compound having a graft-reactive group and a carboxylic anhydride group is an aromatic tricarboxylic anhydride.

11. The thermosetting resin composition according to claim 1, wherein the compound having a graft-reactive group and a carboxylic anhydride group is trimellitic anhydride.

12. The thermosetting resin composition according to claim 1, wherein the amount of the compound having a graft-reactive group and a carboxylic anhydride group used is such that the amount of the graft-reactive group of the compound is 0.01 to 1 mole per mole of the repeating unit of the general formula (1) of the polycarbodiimide.

13. The thermosetting resin composition according to claim 1, wherein the grafting of the compound having a graft-reactive group and a carboxylic anhydride group on the polycarbodiimide is effected in the presence of a solvent.

14. The thermosetting resin composition according to claim 1, wherein the grafting of at least one compound having a graft-reactive group and a carboxylic anhydride group on the polycarbodiimide is effected at a temperature of not more than 100°

C.

15. The thermosetting resin composition according to claim 1, wherein the number average molecular weight of the resin obtained by grafting at least one compound having a graft-reactive group and a carboxylic anhydride on a polycarbodiimide is 500 to 1,000,000.

16. The thermosetting resin composition according to claim 1, wherein the epoxy compound is a compound having at least one epoxy group in the molecule.

17. The thermosetting resin composition according to claim 1, wherein the epoxy compound is an epoxy resin.

18. The thermosetting resin composition according to claim 1, wherein the epoxy resin is at least one epoxy resin selected from the group consisting of glycidyl ether epoxy resins, glycidyl ester epoxy resins, aromatic glycidyl amine epoxy resins, alicyclic epoxy resins, heterocyclic epoxy resins and liquid rubber-modified epoxy resins.

19. The thermosetting resin composition according to claim 1, wherein the amount of the epoxy compound (B) contained is 5 to 500 parts by weight per 100 parts by weight of the resin (A).

20. The thermosetting resin composition according to claim 1, which is obtained by mixing the resin (A) with the epoxy compound (B) in the presence or absence of a solvent.

21. A molded article obtained by molding the thermosetting resin composition according to claim 1.

22. The molded article according to claim 21, which is a heat-curable film or a cured film.