Carboxyl group-containing polyimide, thermosetting resin composition and flexible metal-clad laminate

• US 9,365,717 B2
• Filed: 05/30/2012
• Issued: 06/14/2016
• Est. Priority Date: 05/31/2011
• Status: Active Grant

• Current Assignee: Toyobo Company Limited
• Original Assignee: Toyobo Company Limited
• Inventors: Kawakusu, Tetsuo
• Primary Examiner(s): McCulley, Megan
• Application Number:
  US13/979,750
• Publication Number:
  US 20130310486A1
• Time in Patent Office: 1,476 Days
• Field of Search: 523/451
• US Class Current: 1/1
• CPC Class Codes: C08G 18/346 having four carboxylic acid groups
• CPC Class Codes: C08G 18/7621 being toluene diisocyanate including isomer mixtures
• CPC Class Codes: C08G 18/7671 containing only one alkylene bisphenyl group
• CPC Class Codes: C08G 73/1035 from tetracarboxylic acids or derivatives and diisocyanates
• CPC Class Codes: C08L 79/08 Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors

Abstract

The present invention aims to provide a carboxyl group-containing polyimide, and prepolymer thereof which give a cured product highly satisfying thermosetting property, PCT resistance, solvent resistance and peel strength at the same time. The present invention relates to a terminal acid anhydride group-containing imide prepolymer which is characterized by being produced by reacting an acid anhydride group in a tetracarboxylic acid dianhydride with an isocyanate group in a diisocyanate compound, and a carboxyl group-containing polyimide which is characterized in having such a structure where the chain of said terminal acid anhydride group-containing imide prepolymer is extended via a polyol compound. The present invention also relates to a thermosetting resin composition and a flexible metal-clad laminate which utilize such carboxyl group-containing polyimide.

Claims

1. A thermosetting resin composition to be used as a resist layer of a printed circuit board, comprising a carboxyl group-containing polyimide and an oxirane ring-containing compound, wherein in the carboxyl group-containing polyimide, the chain of a terminal acid anhydride group-containing imide prepolymer is extended via a polycarbonate polyol having a number-average molecular weight of 100 to 30,000, wherein the terminal acid anhydride group-containing imide prepolymer is produced by reacting an acid anhydride group in a tetracarboxylic acid dianhydride with an isocyanate group in a diisocyanate compound, and wherein the thermosetting resin composition has no urethane bonds in the resin skeleton.

2. The thermosetting resin composition according to claim 1, wherein an amount of the oxirane ring-containing compound is 2 to 100 parts by weight to 100 parts by weight of the carboxyl group-containing polyimide.

3. The thermosetting resin composition according to claim 1, further comprising a phosphorus atom-containing organic filler.

4. The thermosetting resin composition according to claim 3, wherein a ratio by weight of the carboxyl group-containing polyimide, the oxirane ring-containing compound and the phosphorus atom-containing organic filler is 30 to 95:

1 to 50;

2 to 55.

5. The thermosetting resin composition according to claim 3, wherein a total weight of the carboxyl group-containing polyimide, the oxirane ring-containing compound and the phosphorus atom-containing organic filler in the thermosetting resin composition is not less than 20% by weight.

6. The thermosetting resin composition according to claim 1, further comprising a curing promoter.