Curable composition, prepreg, resin sheet, metal foil-clad laminate and printed wiring board

Patent metadata

Field	Value
Publication number	US-11718708-B2
Application number	US-202217845200-A
Country	US
Kind code	B2
Filing date	Jun 21, 2022
Priority date	Jul 26, 2018
Publication date	Aug 8, 2023
Grant date	Aug 8, 2023

Abstract

A curable composition is provided that includes an alkenyl phenol A, an epoxy-modified silicone B, an epoxy compound C other than the epoxy-modified silicone B, and a thermosetting resin E, in which the thermosetting resin E contains one or more selected from the group consisting of a maleimide compound, a cyanate ester compound, a phenolic compound, an alkenyl-substituted nadimide compound, and an epoxy compound.

First claim

The invention claimed is:

1. A curable composition comprising:
an alkenyl phenol A, an epoxy-modified silicone B, an epoxy compound C other than the epoxy-modified silicone B, and a thermosetting resin E,
wherein the thermosetting resin E contains one or more selected from the group consisting of a maleimide compound, a cyanate ester compound, a phenolic compound, an alkenyl-substituted nadimide compound, and an epoxy compound, and
the epoxy-modified silicone B contains an epoxy-modified silicone represented by Formula (1):

where each R 1 independently represents an alkylene group, a phenylene group, or an aralkylene group; each R 2 independently represents an alkyl group having from 1 to 10 carbon atoms, or a phenyl group; and n represents an integer of 1 or larger.

2. The curable composition according to claim 1 , wherein the alkenyl phenol A contains a diallyl bisphenol and/or a dipropenyl bisphenol.

3. The curable composition according to claim 1 , wherein the epoxy-modified silicone B contains an epoxy-modified silicone having 140 to 250 g/mol of an epoxy group mol equivalent.

4. The curable composition according to claim 1 , wherein the epoxy compound C contains an epoxy compound represented by Formula (2):

where each R a independently represents an alkyl group having from 1 to 10 carbon atoms, or a hydrogen atom.

5. The curable composition according to claim 1 , wherein a content of the epoxy compound C is from 5 to 50 mass % based on a total amount of 100 mass % of the epoxy-modified silicone B and the epoxy compound C.

6. A curable composition comprising a polymer D containing a constituent unit derived from the alkenyl phenol A, a constituent unit derived from the epoxy-modified silicone B, a constituent unit derived from the epoxy compound C, and a thermosetting resin E,
wherein the thermosetting resin E contains one or more selected from the group consisting of a maleimide compound, a cyanate ester compound, a phenolic compound, an alkenyl-substituted nadimide compound, and an epoxy compound.

7. The curable composition according to claim 6 , wherein a content of the constituent unit derived from the epoxy-modified silicone B in the polymer D is from 20 to 60 mass % based on a total mass of the polymer D.

8. The curable composition according to claim 6 , wherein an alkenyl group mol equivalent of the polymer D is from 300 to 1500 g/mol.

9. The curable composition according to claim 6 , wherein a content of the polymer D is from 5 to 50 mass % based on 100 mass % of resin solids.

10. The curable composition according to claim 1 , wherein
the maleimide compound includes one or more selected from the group consisting of bis(4-maleimidophenyl)methane, 2,2-bis{4-(4-maleimidophenoxy)-phenyl}propane, bi s(3-ethyl-5-methyl-4-maleimidophenyl)methane, and maleimide compounds represented by Formula (3):

where each R 5 independently represents a hydrogen atom or a methyl group; and n 1 represents an integer of 1 or larger.

11. The curable composition according to claim 1 , wherein the cyanate ester compound comprises a compound represented by Formula (4) and/or a compound represented by Formula (5) excluding the compound represented by Formula (4):

where each R 6 independently represents a hydrogen atom or a methyl group; and n 2 represents an integer of 1 or larger; and

where each R ya independently represents an alkenyl group having from 2 to 8 carbon atoms; each R yb independently represents an alkyl group having from 1 to 10 carbon atoms, or a hydrogen atom; each R yc independently represents an aromatic ring having from 4 to 12 carbon atoms, where R yc may form a fused structure with a benzene ring, and R yc may be present or absent; each A 1a independently represents an alkylene group having from 1 to 6 carbon atoms, an aralkylene group having from 7 to 16 carbon atoms, an arylene group having from 6 to 10 carbon atoms, a fluorenylidene group, a sulfonyl group, an oxygen atom, a sulfur atom, or a single bond; when R yc is absent, one benzene ring may have two or more groups of R ya and/or R yb ; and n represents an integer from 1 to 10.

12. The curable composition according to claim 1 , wherein the epoxy compound includes a compound represented by Formula (6) or a compound represented by Formula (7):

where each R 13 independently represents a hydrogen atom, an alkyl group having from 1 to 3 carbon atoms, or an alkenyl group having from 2 to 3 carbon atoms; and

where each R 14 independently represents a hydrogen atom, an alkyl group having from 1 to 3 carbon atoms, or an alkenyl group having from 2 to 3 carbon atoms.

13. The curable composition according to claim 1 , further including an inorganic filler, wherein
a content of the inorganic filler is from 50 to 1000 parts by mass based on 100 parts by mass of resin solids.

14. The curable composition according to claim 1 , wherein
the curable composition is used for a printed wiring board.

15. A prepreg comprising:
a base material; and
the curable composition described in claim 1 with which the base material is impregnated or coated.

16. A resin sheet comprising:
a support; and
the curable composition described in claim 1 disposed on a surface of the support.

17. A metal foil-clad laminate comprising:
a laminate formed of one or more selected from the group consisting of:
the prepreg described in claim 15 ; and
a resin sheet comprising:
a support; and
the curable composition disposed on a surface of the support; and

a metal foil disposed on one or both sides of the laminate.

18. A printed wiring board comprising:
an insulating layer formed of one or more selected from the group consisting of:
the prepreg described in claim 15 ; and
a resin sheet comprising:
a support; and
the curable composition disposed on a surface of the support; and

a conductor layer formed on a surface of the insulating layer.

19. The curable composition according to claim 6 , wherein the maleimide compound includes one or more selected from the group consisting of bis(4-maleimidophenyl)methane, 2,2-bis{4-(4-maleimidophenoxy)-phenyl}propane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, and maleimide compounds represented by Formula (3):

where each R 5 independently represents a hydrogen atom or a methyl group; and n 1 represents an integer of 1 or larger.

20. The curable composition according to claim 6 , wherein the cyanate ester compound comprises a compound represented by Formula (4) and/or a compound represented by Formula (5) excluding the compound represented by Formula (4):

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Tomizawa Katsuya
• Kikuchi Mayumi
• Kawai Hidetoshi

Classifications

• C08J5/24

  Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs · CPC title

• H05K1/0373

  containing additives, e.g. fillers (H05K1/036 takes precedence) · CPC title

• C08J2363/00

  Characterised by the use of epoxy resins; Derivatives of epoxy resins · CPC title

• C08J2383/06

  containing silicon bound to oxygen-containing groups (C08J2383/12 takes precedence) · CPC title

• C08G59/621 Primary

  Phenols · CPC title