Polyimide resin and curable resin composition

• US 8,188,209 B2
• Filed: 03/28/2006
• Issued: 05/29/2012
• Est. Priority Date: 03/28/2005
• Status: Expired due to Fees

• Current Assignee: UBE Industries Limited (UBE Corporation)
• Original Assignee: UBE Industries Limited (UBE Corporation)
• Inventors: Naiki, Masahiro, Takasawa, Ryoichi, Maeda, Shuichi, Hirano, Tetsuji, Kinouchi, Masayuki
• Primary Examiner(s): Gulakowski, Randy
• Assistant Examiner(s): Kahn, Rachel
• Application Number:
  US11/884,348
• Publication Number:
  US 20100113689A1
• Time in Patent Office: 2,254 Days
• Field of Search: 528/85, 528/322, 528/84, 528/353
• US Class Current: 528/85
• CPC Class Codes: C08G 18/0823 containing carboxylate salt groups or groups forming them
• CPC Class Codes: C08G 18/3234 cycloaliphatic
• CPC Class Codes: C08G 18/348 Hydroxycarboxylic acids
• CPC Class Codes: C08G 18/3846 containing imide groups C08G18/3821 takes precedence
• CPC Class Codes: C08G 18/44 Polycarbonates
• CPC Class Codes: C08G 18/542 with phenols
• CPC Class Codes: C08G 18/58 Epoxy resins C08G18/42, C08G18/48 take precedence; reaction products of epoxy resins with at least equivalent amounts of compounds containing active hydrogen C08G18/6407, with at least equivalent amounts of amines C08G18/6415; polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen C08G18/003
• CPC Class Codes: C08G 18/6438 Polyimides or polyesterimides
• CPC Class Codes: C08G 18/6692 with compounds of group C08G18/34
• CPC Class Codes: C08G 18/7671 containing only one alkylene bisphenyl group
• CPC Class Codes: C08G 18/8077 Oximes
• CPC Class Codes: C08G 69/40 Polyamides containing oxygen in the form of ether groups C08G69/12, C08G69/32 take precedence
• CPC Class Codes: C08G 69/44 Polyester-amides
• CPC Class Codes: C08G 73/1007 from tetracarboxylic acids or derivatives and diamines
• CPC Class Codes: C08G 73/16 Polyester-imides
• CPC Class Codes: C08J 2379/08 Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
• CPC Class Codes: C08J 5/18 Manufacture of films or sheets
• 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 2666/22 Macromolecular compounds not provided for in C08L2666/16 - C08L2666/20
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C08L 79/08 : Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
• CPC Class Codes: H05K 3/285 : Permanent coating compositions
• CPC Class Codes: H05K 3/4676 : Single layer compositions

Abstract

A curable polyimide resin composition containing a polyimide resin obtainable from by a reaction of a reaction mixture containing a diisocyanate compound, a carbonate group-containing diol compound and an imide compound having two terminal hydroxyhydrocarbyl groups gives a cured insulation film having improved characteristics.

Claims

1. A polyimide resin comprising the following recurring units (1), (2) and (3);

2. The polyimide resin of claim 1, wherein the A is a divalent aliphatic, alicylic or aromatic hydrocarbon group having 2 to 30 carbon atoms.

3. The polyimide resin of claim 1, wherein the tetracarboxylic acid compound is an aromatic tetracarboxylic acid or a dianhydride thereof.

4. The polyimide resin of claim 1, wherein the diamine compound is an aromatic, alicyclic, or aliphatic diamine.

5. The polyimide resin of claim 1, wherein s and t satisfy the following conditions:

t/s=0.1-10

(s+t)/p=0.5-2.5

wherein p is a molar amount of the diisocyanate compound.

6. A method for preparing a polyimide resin of claim 1, which comprises reacting a diisocyanate compound of the formula (4) and an imide compound of the formula (5):

7. A curable polyimide resin composition comprising 100 weight parts of the polyimide resin of claim 1, 1 to 50 weight parts of an epoxy compound or an isocyanate compound, and an organic solvent.

8. A cured insulation film manufactured by heating a solution film of the polyimide resin composition which comprises 100 weight parts of the polyimide resin of claim 1, 1 to 50 weight parts of an epoxy compound or an isocyanate compound, and an organic solvent.

9. The polyimide resin of claim 1, wherein Y is a divalent group obtainable from an alicyclic diamine by removing two amino groups thereof.

10. The polyimide resin of claim 1, wherein X is a tetravalent residue obtainable from 2,3,3′

,4′

-biphenyltetracarboxylic acid by removing all carboxyl groups thereof.