Cyanate ester compound, curable resin composition containing the same, and hardened product thereof

Patent metadata

Field	Value
Publication number	US-9949369-B2
Application number	US-201415023876-A
Country	US
Kind code	B2
Filing date	Oct 24, 2014
Priority date	Oct 25, 2013
Publication date	Apr 17, 2018
Grant date	Apr 17, 2018

Abstract

The present invention is a cyanate ester compound represented by the following formula (1):

wherein Ar represents an aromatic ring; R 1 each independently represents a hydrogen atom, an alkyl group, or an aryl group; n each independently represents an integer of 1 to 3; m+n is the same as the total number of hydrogen atoms in a monovalent aromatic group containing the aromatic ring and the hydrogen atoms; R 2 represents a hydrogen atom (excluding a case where Ar represents a benzene ring; n each represents 1; R 1 represents a hydrogen atom; m each represents 4, and a cyanate group is bonded to the benzene ring in the 4-position relative to an adamantyl group), or an alkyl group having 1 to 4 carbon atoms; and R 3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

First claim

The invention claimed is:

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

wherein Ar represents an aromatic ring; R 1 each independently represents a hydrogen atom, an alkyl group, or an aryl group; n each independently represents an integer of 1 to 3; m+n is the same as the total number of hydrogen atoms in a monovalent aromatic group comprising the aromatic ring and the hydrogen atoms; R 2 represents a hydrogen atom (excluding a case where Ar represents a benzene ring; n each represents 1; R 1 represents a hydrogen atom; m each represents 4, and a cyanate group is bonded to the benzene ring in the 4-position relative to an adamantyl group), or an alkyl group having 1 to 4 carbon atoms; and R 3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

2. The cyanate ester compound according to claim 1 , wherein, in the formula (1), Ar represents a benzene ring; n represents 1; and R 2 represents a methyl group, an ethyl group, a propyl group, an isopropyl group, or a t-butyl group.

3. The cyanate ester compound according to claim 1 , wherein Ar represents a benzene ring; and n represents 2 or 3.

4. The cyanate ester compound according to claim 1 , wherein Ar represents an aromatic ring other than a benzene ring.

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

wherein Ar represents an aromatic ring; R 1 each independently represents a hydrogen atom, an alkyl group, or an aryl group; n represents an integer of 1 to 3; m+n represents an integer representing the total number of monovalent atoms and groups bonded to Ar; R 2 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; and R 3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

6. The curable resin composition according to claim 5 , further comprising one or more selected from the group consisting of a cyanate ester compound other than the cyanate ester compound represented by the formula (1), an epoxy resin, an oxetane resin, and a compound having a polymerizable unsaturated group.

7. The curable resin composition according to claim 5 , wherein, in the cyanate ester compound represented by the formula (1), Ar represents a benzene ring; n represents 1; and R 2 represents a methyl group, an ethyl group, a propyl group, an isopropyl group, or a t-butyl group.

8. The curable resin composition according to claim 5 , wherein, in the cyanate ester compound represented by the formula (1), Ar represents a benzene ring, and n represents 2 or 3.

9. The curable resin composition according to claim 5 , wherein, in the cyanate ester compound represented by the formula (1), Ar represents an aromatic ring other than a benzene ring.

10. A hardened product obtained by curing the curable resin composition according to claim 5 .

11. A prepreg for structural materials comprising a base material and the curable resin composition according to claim 5 with which the base material is impregnated or coated.

12. A sealing material comprising the curable resin composition according to claim 5 .

13. A fiber-reinforced composite material comprising the curable resin composition according to claim 5 .

14. An adhesive comprising the curable resin composition according to claim 5 .

15. The curable resin composition according to claim 5 , further comprising an epoxy resin.

16. The curable resin composition according to claim 15 , wherein a content of the cyanate ester compound represented by the formula (1) is 1 to 90 parts by mass based on 100 parts by mass of a resin solid content in the curable resin composition.

17. The curable resin composition according to claim 15 , further comprising an inorganic filler.

18. The curable resin composition according to claim 17 , wherein a content of the inorganic filler is 50 to 1600 parts by mass based on 100 parts by mass of a resin solid content in the curable resin composition.

19. The curable resin composition according to claim 15 , further comprising one or more selected from the group consisting of a maleimide compound, a phenolic resin, and a cyanate ester compound other than the cyanate ester compound represented by the formula (1).

20. The curable resin composition according to claim 15 , wherein the epoxy resin is one or more selected from the group consisting of a biphenyl aralkyl-based epoxy resin, a naphthylene ether-based epoxy resin, a multifunctional phenol-based epoxy resin, and a naphthalene-based epoxy resin.

21. A metal foil clad laminate comprising one or more of the prepreg according to claim 11 and a metallic foil disposed on one or both surfaces of the prepreg.

22. A laminate comprising a support and a resin layer formed on a surface of the support by coating and drying of the curable resin composition according to claim 5 .

23. A printed wiring board comprising an insulating layer and a conductor layer formed on a surface of the insulating layer, wherein the insulating layer comprises the curable resin composition according to claim 5 .

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Katagiri Masayuki
• Tokuzumi Keita
• Tsubuku Makoto
• Tsujimoto Tomoo
• Arii Kenji
• Kobayashi Takashi
• Sogame Masanobu
• Mabuchi Yoshinori
• Hiramatsu Sotaro

Classifications

• 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

• C08L79/04

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors · CPC title

• C08G73/0655

  from polycyanurates · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C08L71/00

  Compositions of polyethers obtained by reactions forming an ether link in the main chain (of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06); Compositions of derivatives of such polymers · CPC title