Cyanate ester compound, curable resin composition containing cyanate ester compound, and cured product thereof

Patent metadata

Field	Value
Publication number	US-9453126-B2
Application number	US-201113878584-A
Country	US
Kind code	B2
Filing date	Oct 25, 2011
Priority date	Oct 29, 2010
Publication date	Sep 27, 2016
Grant date	Sep 27, 2016

Abstract

There is provided a novel dicyanatophenyl-based difunctional cyanate ester which is in a liquid form at ordinary temperature and can obtain a cured product having an excellent low thermal expansion rate. There is disclosed a cyanate ester compound represented by the following formula (I):

(wherein R 1 represents a hydrocarbon group having 2 to 20 carbon atoms).

First claim

The invention claimed is:

1. A cyanate ester compound (A) represented by the following formula (I):

wherein the cyanate ester compound is 1,1-bis(4-cyanatophenyl)isobutane.

2. A curable resin composition comprising a cyanate ester compound (A) according to claim 1 .

3. The curable resin composition according to claim 2 , wherein the curable resin composition is a non-crystalline liquid at 50° C.

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

wherein R 2 represents any one selected from the group consisting of the following general formulae (i) to (v):

wherein each of R 3 and R 4 represents a hydrogen atom, or an alkyl group having 1 to 8 carbon atoms or a trifluoromethyl group, and n represents an integer of 4 to 7;
or the following general formula (III):

wherein R 5 represents hydrogen or a methyl group; n represents an integer of 1 to 50; and the cyanate ester compound (B) represented by the general formula (III) may be a mixture of compounds having different n, an epoxy resin (C), and a maleimide compound (D).

5. The curable resin composition according to claim 4 , wherein the epoxy resin is one or more selected from the group consisting of a bisphenol A-based epoxy resin, a bisphenol F-based epoxy resin, a phenol novolac-based epoxy resin, and a dihydroxy naphthalene-based epoxy resin.

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

wherein each of R 5 and R 6 independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 3 carbon atoms; each of e and f represents an integer of 1 to 4; and M represents a single bond, an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 1 to 5 carbon atoms, or an arylene group having 6 to 14 carbon atoms.

7. A curable resin composition comprising a cyanate ester compound (A) selected from the group consisting of
1,1-bis(4-cyanatophenyl)isobutane,
1,1-bis(4-cyanatophenyl)-3-methylbutane,
1,1-bis(4-cyanatophenyl)-2-methylbutane,
1,1-bis(4-cyanatophenyl)-2,2-dimethylpropane,
1,1-bis(4-cyanatophenyl)-4-methylpentane,
1,1-bis(4-cyanatophenyl)-3-methylpentane,
1,1-bis(4-cyanatophenyl)-2-methylpentane,
1,1-bis(4-cyanatophenyl)-2,3-dimethylbutane,
1,1-bis(4-cyanatophenyl)-3,3-dimethylbutane,
bis(4-cyanatophenyl)cyclopentylmethane,
bis(4-cyanatophenyl)cyclohexyl methane,
bis(4-cyanatophenyl)phenylmethane,
1,1-bis(4-cyanatophenyl)-2-methylhexane,
1,1-bis(4-cyanatophenyl)-3-methylhexane,
1,1-bis(4-cyanatophenyl)-4-methylhexane,
1,1-bis(4-cyanatophenyl)-5-methylhexane,
1,1-bis(4-cyanatophenyl)-3,4-dimethylpentane,
1,1-bis(4-cyanatophenyl)-2,3-dimethylpentane,
1,1-bis(4-cyanatophenyl)-3-ethylpentane,
1,1-bis(4-cyanatophenyl)-2-ethylpentane,
bis(4-cyanatophenyl)-1-naphthylmethane,
1,1-bis(4-cyanatophenyl)-2-phenylmethylhexane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)propane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)butane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)isobutane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)pentane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-3-methylbutane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-2-methylbutane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-2,2-dimethylpropane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)hexane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-4-methylpentane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-3-methylpentane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-2-methylpentane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-2,3-dimethylbutane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-3,3-dimethylbutane,
[(2-cyanatophenyl)-(4-cyanatophenyl)methyl]cyclopentane,
[(2-cyanatophenyl)-(4-cyanatophenyl)methyl]cyclohexane,
2,4′-dicyanatotriphenylmethane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)heptane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-2-methylhexane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-3-methylhexane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-4-methylhexane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-5-methylhexane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-3,4-dimethylpentane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-2,3-dimethylpentane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-3-ethylpentane,
1-(2-cyanatophenyl)-1-(4-cyanatophenyl)-2-ethylpentane, and
[(2-cyanatophenyl)-(4-cyanatophenyl)methyl]naphthalene, and
further comprising one or more selected from the group consisting of a cyanate ester compound (B) represented by the following general formula (II):

wherein R 2 represents any one selected from the group consisting of the following general formulae (i) to (v):

wherein each of R 1 and R 4 represents a hydrogen atom, or an alkyl group having 1 to 8 carbon atoms or a trifluoromethyl group, and n represents an integer of 4 to 7;
or the following general formula (III):

wherein R 5 represents hydrogen or a methyl group; n represents an integer of 1 to 50; and the cyanate ester compound (B) represented by the general formula (III) may be a mixture of compounds having different n, an epoxy resin (C), and a maleimide compound (D); and
wherein the curable resin composition comprises 0 to 250 parts by mass of the cyanate ester compound (B), 0 to 250 parts by mass of the epoxy resin (C), and 0 to 100 parts by mass of the maleimide compound (D), based on 100 parts by mass of the cyanate ester compound (A).

8. The curable resin composition according to claim 7 , wherein the curable resin composition comprises 0 to 100 parts by mass of the cyanate ester compound (B), 0 to 100 parts by mass of the epoxy resin (C), and 0 to 50 parts by mass of the maleimide compound (D), based on 100 parts by mass of the cyanate ester compound (A).

9. A curable resin composition comprising a cyanate ester compound (A) selected from the group consisting of
1,1-bis(4-cyanatophenyl)isobutane,
1,1-bis(4-cyanatophenyl)-3-methylbutane,
1,1-bis(4-cyanatophenyl)-2-methylbutane,
1,1-bis(4-cyanatophenyl)-2,2-dimethylpropane,
1,1-bis(4-cyanatophenyl)-4-methylpentane,
1,1-bis(4-cyanatophenyl)-3-methylpentane,
1,1-bis(4-cyanatophenyl)-2-methylpentane,
1,1-bis(4-cyanatophenyl)-2,3-dimethylbutane,
1,1-bis(4-cyanatophenyl)-3,3-dimethylbutane,
bis(4-cyanatophenyl)cyclopentylmethane,
bis(4-cyanatophenyl)cyclohexyl methane,
bis(4-cyanatophenyl)phenylmethane,
1,1-bis(4-cyanatophenyl)-2-methylhexane,
1,1-bis(4-cyanatophenyl)-3-methylhexane,
1,1-bis(4-cyanatophenyl)-4-methylhexane,
1,1-bis(4-cyanatophenyl)-5-methylhexane,
1,1-bis(4-cyanatophenyl)-3,4-dimethylpentane,
1,1-bis(4-cyanatophenyl)-2,3-dimethylpentane,
1,1-bis(4-cyanatophenyl)-3-ethylpentane,
1,1-bis(4-cyanatophenyl)-2-ethylpentane,
bis(

Assignees

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

Inventors

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

Classifications

• C08G59/4014

  Nitrogen containing compounds · CPC title

• C08G73/0655

  from polycyanurates · CPC title

• C08L79/00

  Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00 · CPC title

• C09J163/00

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title

• C08L79/085

  Unsaturated polyimide precursors · CPC title