Fluorene derivative, method for producing the same, resin composition, and article

Patent metadata

Field	Value
Publication number	US-10696878-B2
Application number	US-201815878845-A
Country	US
Kind code	B2
Filing date	Jan 24, 2018
Priority date	Jan 27, 2017
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

In the General Formula (1), X1 represents a cyclic carbonate group including a carbonate bond [—O—C(═O)—O—], X2 represents a cyclic carbonate group including a carbonate bond [—O—C(═O)—O—], and Y represents a bivalent group including a 9,9-bisaryl fluorene skeleton.

First claim

What is claimed is:

1. A fluorene derivative represented by General Formula (1) below:
X 1 —Y—X 2   General Formula (1)

where in the General Formula (1), X 1 represents a cyclic carbonate group including a carbonate bond [—O—C(═O)—O—], X 2 represents a cyclic carbonate group including a carbonate bond [—O—C(═O)—O—], and Y represents a bivalent group represented by General Formula (Y1) below:

where in the General Formula (Y1), ring Z each represents an aromatic hydrocarbon ring, R 1 each independently represents a cyano group, a halogen atom, or a hydrocarbon group, R 2 each independently represents an alkylene group, R 3 each independently represents a hydrocarbon group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an arallcyloxy group, an alkylthio group, a cycloalkylthio group, an arylthio group, an aralkylthio group, an acyl group, an alkoxycarbonyl group, a hydroxy group, a halogen atom, a nitro group, a cyano group, or a dialkyamino group, k each independently represents an integer of 0 to 4, m each independently represents an integer of 0 or 1 or more, and n each independently represents an integer of 0 or 1 or more.

2. The fluorene derivative according to claim 1 , wherein the group represented by the X 1 is a group represented by General Formula (X1) below and the group represented by the X 2 is a group represented by General Formula (X2) below:

where in the General Formula (X1), R 11 represents an alkyl group, R 13 represents an alkylene group, and p represents 0 or 1; and in the General Formula (X2), R 12 represents an alkyl group, R 14 represents an alkylene group, and p represents an integer of 0 or 1.

3. The fluorene derivative according to claim 1 , wherein the fluorene derivative is represented by General Formula (Z31) below:

where in the General Formula (Z31), R 21 each represents an alkyl group, R 24 each represents an alkylene group, ring Z each represents an aromatic hydrocarbon ring, R 1 each independently represents a cyano group, a halogen atom, or a hydrocarbon group, R 2 each independently represents an alkylene group, R 3 each independently represents a hydrocarbon group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aralkyloxy group, an alkylthio group, a cycloalkylthio group, an arylthio group, an aralkylthio group, an acyl group, an alkoxycarbonyl group, a hydroxy group, a halogen atom, a nitro group, a cyano group, or a dialkylamino group, k each independently represents an integer of 0 to 4, m each independently represents an integer of 0 or 1 or more, n each independently represents an integer of 0 or 1 or more, and p each represents an integer of 0 or 1.

4. The fluorene derivative according to claim 1 , wherein the fluorene derivative is represented by General Formula (Z32) below:

where in the General Formula (Z32), R 21 each represents an alkyl group, and p each represents an integer of 0 or 1.

5. A resin composition comprising
the fluorene derivative according to claim 1 .

6. The resin composition according to claim 5 , further comprising
an epoxy compound.

7. The resin composition according to claim 6 , wherein a mass ratio between the fluorene derivative and the epoxy compound (the fluorene derivative:the epoxy compound) is 0.1:99.9 to 15:85.

8. The resin composition according to claim 6 , wherein the mass ratio between the fluorene derivative and the epoxy compound (the fluorene derivative:the epoxy compound) is 1:99 to 5:95.

9. The resin composition according to claim 5 , wherein a volume change rate before and after curing is 5.00% or less.

10. An article comprising
a cured product of the resin composition according to claim 5 .

11. A method for producing a fluorene derivative, the method comprising:
reacting a compound represented by General Formula (X3) below with a compound represented by General Formula (Y21) below to obtain a fluorene derivative represented by General Formula (Z11) below;
converting the fluorene derivative represented by General Formula (Z11) into a fluorene derivative represented by General Formula (Z21) below; and
converting the fluorene derivative represented by General Formula (Z21) into a fluorene derivative represented by General Formula (Z31) below to obtain the fluorene derivative represented by General Formula (Z31),

where in the General Formula (X3), R 21 each represents an alkyl group, R 22 each represents an alkyl group, R 23 each represents an alkyl group, R 24 each represents an alkylene group, R 25 represents a para-toluenesulfonyl group or an alkylsulfonyl group, and p each represents an integer of 0 or 1,

where in the General Formula (Y21), the General Formula (Z11), the General Formula (Z21), and the General Formula (Z31), R 21 each represents an alkyl group, R 22 each represents an alkyl group, R 23 each represents an alkyl group, R 24 each represents an alkylene group, ring Z each represents an aromatic hydrocarbon ring, R 1 each independently represents a cyano group, a halogen atom, or a hydrocarbon group, R 2 each independently represents an alkylene group, R 3 each independently represents a hydrocarbon group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aralkyloxy group, an alkylthio group, a cycloalkylthio group, an arylthio group, an aralkylthio group, an acyl group, an alkoxycarbonyl group, a hydroxy group, a halogen atom, a nitro group, a cyano group, or a dialkylamino group, k each independently represents an integer of 0 to 4, m each independently represents an integer of 0 or 1 or more, n each independently represents an integer of 0 or 1 or more, and p each represents an integer of 0 or 1.

Assignees

• Dexerials Corp
• Univ Kinki

Inventors

• Chiba Hiroto
• Abe Tetsuya
• Lee Sungkil
• Ito Makiya
• Endo Takeshi

Classifications

• C08G59/68

  characterised by the catalysts used · CPC title

• C08G59/24

  carbocyclic · CPC title

• C08G59/40

  characterised by the curing agents used · CPC title

• C09J163/00 Primary

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

• C07D407/12

  linked by a chain containing hetero atoms as chain links · CPC title