Curable resin composition and cured product thereof

Patent metadata

Field	Value
Publication number	US-9657173-B2
Application number	US-201213978310-A
Country	US
Kind code	B2
Filing date	Jan 31, 2012
Priority date	Feb 4, 2011
Publication date	May 23, 2017
Grant date	May 23, 2017

Abstract

A curable resin composition which can achieve a cured product in which the generation of cracks upon curing is suppressed and which has both a low thermal expansion rate and a low water absorbability is provided. The curable resin composition comprises: at least a cyanate ester compound (A) represented by the following formula (I); a metal complex catalyst (B); and an additive (C), wherein the additive (C) contains any one or more selected from the group consisting of a compound represented by the following general formula (II), a compound represented by the following general formula (III), and a tertiary amine.

First claim

The invention claimed is:

1. A curable resin composition comprising:
at least a cyanate ester compound (A) represented by the following formula (I):

a metal complex catalyst (B); and
an additive (C),
wherein the additive (C) a compound represented by the following general formula (III):

wherein R 6 to R 10 each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a hydroxy group; and
an amount of the cyanate ester compound (A) is 60 to 100 weight % based on total amount of cyanate ester compounds.

2. The curable resin composition according to claim 1 , further comprising one or more selected from the group consisting of:
a cyanate ester compound (D) represented by the following general formula (IV):

wherein R 11 is any one selected from the group consisting of the following general formulae (i) to (vi):

wherein R 12 , R 13 , and R 14 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a trifluoromethyl group, and 1 is an integer of 4 to 7,
the following general formula (V):

wherein R 15 represents a hydrogen atom or a methyl group, and m represents an integer of 1 to 50, or
the following general formula (VI):

wherein R 16 to R 18 are each independently a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, or a phenyl group, and n represents an integer of 1 to 50;
an epoxy resin (E); and
a maleimide compound (F).

3. The curable resin composition according to claim 2 , wherein the epoxy resin (E) is one or more selected from the group consisting of a bisphenol A-based epoxy resin, a bisphenol F-based epoxy resin, a naphthalene-based epoxy resin, an anthracene-based epoxy resin, a dihydroxynaphthalene-based epoxy resin, a biphenyl-based epoxy resin, a phenol novolac-based epoxy resin, a phenol aralkyl-based epoxy resin, a biphenyl aralkyl-based epoxy resin, a naphthol aralkyl-based epoxy resin, and an alicyclic epoxy resin.

4. The curable resin composition according to claim 2 , wherein the maleimide compound (F) is a compound represented by the following general formula (VII):

wherein
R 19 and R 20 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 3 carbon atoms;
p+q=4 is set; and
R 21 represents a single bond, an ether bond, a sulfide bond, a sulfone bond, an alkylene group having 1 to 5 carbon atoms, an alkylidene group, an arylene group having 6 to 14 carbon atoms, or an aryleneoxy group.

5. The curable resin composition according to claim 4 , wherein the maleimide compound (F) is at least one selected from the group consisting of 4,4′-diphenyl methane bismaleimide, 2,2′-bis-[4-(4-maleimidephenoxy)phenyl]propane, and 3,3′-dimethyl-5,5′-diethyl-4,4′-diphenyl methane bismaleimide.

6. The curable resin composition according to claim 2 , wherein the curable resin composition comprises 1 to 250 parts by mass of the cyanate ester compound (D) based on 100 parts by mass of the cyanate ester compound (A).

7. The curable resin composition according to claim 2 , wherein the curable resin composition comprises 1 to 250 parts by mass of the epoxy resin (E) based on 100 parts by mass of the cyanate ester compound (A).

8. The curable resin composition according to claim 2 , wherein the curable resin composition comprises 1 to 100 parts by mass of the maleimide compound (F) based on 100 parts by mass of the cyanate ester compound (A).

9. The curable resin composition according to claim 1 , wherein the metal complex catalyst (B) is one or more selected from the group consisting of an octoate, a naphthenate, and an acetylacetone complex of manganese, iron, cobalt, nickel, copper, or zinc.

10. The curable resin composition according to claim 1 , wherein the additive (C) is one or more selected from the group consisting of 1 naphthol, 2-naphthol, and dihydroxynaphthalene.

11. The curable resin composition according to claim 1 , wherein the curable resin composition comprises 0.01 to 5 parts by mass of the metal complex catalyst (B) based on 100 parts by mass of the cyanate ester compound (A).

12. The curable resin composition according to claim 1 , wherein the curable resin composition comprises 0.01 to 10 parts by mass of the additive (C) based on 100 parts by mass of the cyanate ester compound (A).

13. A cured product obtained by curing the curable resin composition according to claim 1 .

14. A sealing material comprising the curable resin composition according to claim 1 .

15. An adhesive comprising the curable resin composition according to claim 1 .

16. A casting material comprising the curable resin composition according to claim 1 .

17. A prepreg comprising: a base material; and the curable resin composition according to claim 1 impregnated into or coated on the base material.

18. A laminated sheet obtained by stacking at least one prepreg according to claim 17 , disposing a metal foil on one side or both sides of the prepreg or the stacked prepregs, and laminate-molding the metal foil and the prepreg or the stacked prepregs.

Assignees

• Tsubuku Makoto
• Ikeno Taketo
• Katagiri Masayuki
• Tsujimoto Tomoo
• Mitsubishi Gas Chemical Co

Inventors

• Tsubuku Makoto
• Ikeno Taketo
• Katagiri Masayuki
• Tsujimoto Tomoo

Classifications

• C09K2200/0645

  obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds · CPC title

• Y10T428/31678

  Of metal · CPC title

• C08G73/0655

  from polycyanurates · CPC title

• C08L75/06 Primary

  from polyesters · CPC title

• C08J2363/00

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