Resin, method for producing resin, curable resin composition, and cured product

Patent metadata

Field	Value
Publication number	US-12540243-B2
Application number	US-202118018985-A
Country	US
Kind code	B2
Filing date	Jul 2, 2021
Priority date	Aug 12, 2020
Publication date	Feb 3, 2026
Grant date	Feb 3, 2026

Abstract

To provide a novel resin having excellent dielectric properties, a method for producing the resin, a curable resin composition, and a cured product. The resin contains constituent units described in Group (1). R 1 each independently represent a methylene group, a methylene oxy group, a methylene oxy methylene group, or an oxy methylene group. R 2 and R 3 each independently represent a halogen atom, an alkyl group having from 1 to 10 carbons, a halogenated alkyl group having from 1 to 10 carbons, a hydroxy alkyl group having from 1 to 10 carbons, or an aryl group having from 6 to 12 carbons. R 4 , R 5 , and R 6 each independently represent a hydrogen atom, a halogen atom, an alkyl group having from 1 to 10 carbons, a halogenated alkyl group having from 1 to 10 carbons, a hydroxy group, a hydroxy alkyl group having from 1 to 10 carbons, or an aryl group having from 6 to 12 carbons.

First claim

The invention claimed is:

1 . A resin comprising constituent units described in Group (1):

where R 1 each independently represent a methylene group, a methylene oxy group, a methylene oxy methylene group, or an oxy methylene group, R 2 and R 3 each independently represent a halogen atom, an alkyl group having from 1 to 10 carbons, a halogenated alkyl group having from 1 to 10 carbons, a hydroxy alkyl group having from 1 to 10 carbons, or an aryl group having from 6 to 12 carbons, R 4 , R 5 , and R 6 each independently represent a hydrogen atom, a halogen atom, an alkyl group having from 1 to 10 carbons, a halogenated alkyl group having from 1 to 10 carbons, a hydroxy group, a hydroxy alkyl group having from 1 to 10 carbons, or an aryl group having from 6 to 12 carbons, x represents 0 or 1, and y and z each independently represent a number of 0 to 3, a, b, and c each independently represent a molar ratio of the constituent units, a represents a number of 1 or greater, b represents a number of 0 or greater, and c represents a number of 1 or greater, R 1 may bond each other to form a crosslinking structure, and * represents a bonding position with another constituent unit or a terminal group.

2 . The resin according to claim 1 , wherein, in Group (1), R 4 , R 5 , and R 6 each independently represent a hydrogen atom.

3 . The resin according to claim 1 , wherein, in Group (1), R 2 and R 3 each independently represent an alkyl group having from 1 to 10 carbons.

4 . The resin according to claim 1 , wherein, in Group (1), R 2 and R 3 each independently represent an alkyl group having from 1 to 5 carbons.

5 . The resin according to claim 1 , wherein 0.2≤a/(b+c)≤5 is satisfied in Group (1).

6 . The resin according to claim 1 , wherein the constituent units described in Group (1) contain at least one type selected from the group consisting of constituent units described in Group (1-1), constituent units described in Group (1-2), and constituent units described in Group (1-3),

where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , x, y, z, a1, b, and c are respectively synonymous with R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , x, y, z, a, b, and c of Group (1), and * represents a bonding position with another constituent unit or a terminal group,

where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , x, y, z, a2, b, and c are respectively synonymous with R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , x, y, z, a, b, and c of Group (1), and * represents a bonding position with another constituent unit or a terminal group,

where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , x, y, z, a3, b, and c are respectively synonymous with R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , x, y, z, a, b, and c of Group (1), and * represents a bonding position with another constituent unit or a terminal group.

7 . The resin according to claim 6 , wherein the constituent units described in Group (1) contain the constituent units described in Group (1-1).

8 . The resin according to claim 1 , wherein a number average molecular weight (Mn) is from 500 to 4000, and a weight average molecular weight (Mw) is from 500 to 7000.

9 . The resin according to claim 1 , wherein a terminal group of the resin is selected from the group consisting of a hydrogen atom, a hydroxy group, and a hydroxymethyl group.

10 . A resin being a reaction product of a resin containing constituent units described in Group (2) and a compound represented by Formula (3),

where R 1 each independently represent a methylene group, a methylene oxy group, a methylene oxy methylene group, or an oxy methylene group, R 2 and R 3 each independently represent a halogen atom, an alkyl group having from 1 to 10 carbons, a halogenated alkyl group having from 1 to 10 carbons, a hydroxy alkyl group having from 1 to 10 carbons, or an aryl group having from 6 to 12 carbons, x represents 0 or 1, and y and z each independently represent a number of 0 to 3, a, b, and c each independently represent a molar ratio of the constituent units, a represents a number of 1 or greater, b represents a number of 0 or greater, and c represents a number of 1 or greater, R 1 may bond each other to form a crosslinking structure, and * represents a bonding position with another constituent unit or a terminal group,

where R 4 , R 5 , and R 6 each independently represent a hydrogen atom, a halogen atom, an alkyl group having from 1 to 10 carbons, a halogenated alkyl group having from 1 to 10 carbons, a hydroxy group, a hydroxy alkyl group having from 1 to 10 carbons, or an aryl group having from 6 to 12 carbons, and L represents a halogen atom.

11 . The resin according to claim 10 , wherein a hydroxy group equivalent of the resin containing the constituent units described in Group (2) is from 200 to 400 g/eq.

12 . A method for producing a resin, the method comprising reacting a resin containing constituent units described in Group (2) and a compound represented by Formula (3) in the presence of a basic compound,

where R 1 each independently represent a methylene group, a methylene oxy group, a methylene oxy methylene group, or an oxy methylene group, R 2 and R 3 each independently represent a halogen atom, an alkyl group having from 1 to 10 carbons, a halogenated alkyl group having from 1 to 10 carbons, a hydroxy alkyl group having from 1 to 10 carbons, or an aryl group having from 6 to 12 carbons, x represents 0 or 1, and y and z each independently represent a number of 0 to 3, a, b, and c each independently represent a molar ratio of the constituent units, a represents a number of 1 or greater, b represents a number of 0 or greater, and c represents a number of 1 or greater, R 1 may bond each other to form a crosslinking structure, and * represents a bonding position with another constituent unit or a terminal group,

where R 4 , R 5 , and R 6 each independently represent a hydrogen atom, a halogen atom, an alkyl group having from 1 to 10 carbons, a halogenated alkyl group having from 1 to 10 carbons, a hydroxy group, a hydroxy alkyl group having from 1 to 10 carbons, or an aryl group having from 6 to 12 carbons, and L represents a halogen atom.

13 . The method according to claim 12 , wherein, in Formula (3), R 4 , R 5 , and R 6 are each a hydrogen atom, and L is a chlorine atom.

14 . The method according to claim 12 , wherein, in Group (2), R 2 and R 3 each independently represent an alkyl group having from 1 to 10 carbons.

15 . The method according to claim 12 , wherein, in Group (2), R 2 and R 3 each independently represent an alkyl group having from 1 to 5 carbons.

16 . The method according to claim 12 , wherein 0.2≤a/(b+c)≤5 is satisfied in Group (2).

17 . The method according to claim 12 , wherein the constituent units

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Uotani Takuya
• Takano Yoichi
• Innan Susumu
• Itoh Syouichi
• Yoshinaka Satoshi
• Suzuki Mika
• Ogiwara Masashi
• Oka Hiroaki

Classifications

• C08G59/62

  Alcohols or phenols · CPC title

• C08G10/00 Primary

  Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only · CPC title

• C08G8/30 Primary

  by unsaturated compounds, e.g. terpenes · CPC title

• C08F299/02

  from unsaturated polycondensates · CPC title

• C08L65/04 Primary

  Polyxylenes · CPC title