Epoxy polymer, epoxy resin, epoxy resin composition, resin sheet, b-stage sheet, cured product, c-stage sheet, metal foil with resin, metal substrate and method for manufacturing

Patent metadata

Field	Value
Publication number	US-11535700-B2
Application number	US-201716491654-A
Country	US
Kind code	B2
Filing date	Mar 9, 2017
Priority date	Mar 9, 2017
Publication date	Dec 27, 2022
Grant date	Dec 27, 2022

Abstract

Provided is an epoxy polymer which has a mesogen skeleton and a structural unit represented by Formula (A). In Formula (A), each R 5 independently represents an alkyl group having from 1 to 8 carbon atoms, and n represents an integer of 0 to 3.

First claim

The invention claimed is:

1. An epoxy polymer comprising:
a mesogen skeleton; and
a structural unit represented by the following Formula (A):

wherein, in Formula (A), each R 5 independently represents an alkyl group having from 1 to 8 carbon atoms; and n represents an integer of 0 to 3,
wherein the epoxy polymer is a reaction product obtained by reacting an epoxy compound that has a mesogen skeleton and two epoxy groups with a trihydric phenol compound that has three hydroxy groups on a single benzene ring as substituents with a ratio (Ep/Ph) between the number of equivalents of the epoxy groups of the epoxy compound (Ep) and the number of equivalents of the phenolic hydroxy groups of the trihydric phenol compound (Ph) being set in a range of from 100/30 to 100/15,
wherein the trihydric phenol compound is at least one selected from the group consisting of 1,2,4-trihydroxybenzene and 1,3,5-trihydroxybenzene,
wherein the epoxy polymer includes at least one selected from the group consisting of a structural unit represented by the following Formula (IA) and a structural unit represented by the following Formula (TB):

wherein, in Formula (IA) and Formula (TB), each of R 1 to R 4 independently represents a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms; each R 5 independently represents an alkyl group having from 1 to 8 carbon atoms; and n represents an integer of 0 to 3.

2. The epoxy polymer according to claim 1 , having a number-average molecular weight of from 1,000 to 3,000 as measured by gel permeation chromatography.

3. The epoxy polymer according to claim 1 , wherein the epoxy compound comprises a compound represented by the following Formula (I):

wherein, each of R 1 to R 4 independently represents a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms.

4. The epoxy polymer according to claim 1 , wherein the epoxy compound comprises trans-4-{4-(2,3-epoxypropoxy)phenyl}cyclohexyl=4-(2,3-epoxypropoxy)benzoate.

5. An epoxy resin comprising the epoxy polymer according to claim 1 .

6. An epoxy resin composition comprising:
the epoxy resin according to claim 5 ; and
a filler.

7. A binder of a carbon fiber-reinforced plastic (CFRP) comprising the epoxy resin composition according to claim 6 .

8. A sealing material or a molding material comprising the epoxy resin composition according to claim 6 .

9. The epoxy resin composition according to claim 6 , having a glass transition temperature of 180° C. or higher when made into a cured product.

10. The epoxy resin composition according to claim 6 , having a diffraction peak in a diffraction angle (2θ) range of from 3.0° to 3.5° when made into a cured product, as determined by X-ray diffractometry using CuKα radiation.

11. A resin sheet comprising a resin composition layer that contains the epoxy resin composition according to claim 6 .

12. A B-stage sheet comprising a semi-cured resin composition layer that contains a semi-cured product of the epoxy resin composition according to claim 6 .

13. A C-stage sheet comprising a cured resin composition layer that contains a cured product of the epoxy resin composition according to claim 6 .

14. A cured product of the epoxy resin composition according to claim 6 .

15. The cured product according to claim 14 , having a glass transition temperature of 180° C. or higher.

16. The cured product according to claim 14 , having a diffraction peak in a diffraction angle (2θ) range of from 3.0° to 3.5° as determined by X-ray diffractometry using CuKα radiation.

17. A metal foil with a resin, comprising:
a metal foil; and
a semi-cured resin composition layer which is arranged on the metal foil and comprises a semi-cured product of the epoxy resin composition according to claim 6 .

18. A metal substrate comprising:
a metal support;
a cured resin composition layer which is arranged on the metal support and comprises a cured product of the epoxy resin composition according to claim 6 ; and
a metal foil arranged on the cured resin composition layer.

19. A method of producing an epoxy resin containing the epoxy polymer according to claim 1 by allowing the epoxy compound that has a mesogen skeleton and two epoxy groups to react with the trihydric phenol compound that has three hydroxy groups on a single benzene ring as substituents.

20. The method of producing an epoxy resin according to claim 19 , wherein the epoxy compound is allowed to react with the trihydric phenol compound, with a ratio (Ep/Ph) between the number of equivalents of the epoxy groups of the epoxy compound (Ep) and the number of equivalents of the phenolic hydroxy groups of the trihydric phenol compound (Ph) being set in a range of from 100/30 to 100/15.

21. The method of producing an epoxy resin according to claim 19 , wherein the trihydric phenol compound is at least one selected from the group consisting of 1,2,4-trihydroxybenzene, and 1,3,5-trihydroxybenzene.

Assignees

• Showa Denko Materials Co Ltd

Inventors

• Katagi Hideyuki
• Maruyama Naoki
• Yoshida Yuka
• HIGASHIUCHI Tomoko
• Takezawa Yoshitaka

Classifications

• C08J5/042

  with carbon fibres · CPC title

• B32B2255/26

  Polymeric coating · CPC title

• C08K3/04

  Carbon · CPC title

• B32B15/092

  comprising epoxy resins · CPC title

• C08G59/621 Primary

  Phenols · CPC title