Methods for producing polycyclic aromatic aminophenol compound and resin composition, and polycyclic aromatic aminophenol compound, resin composition, and cured product

Patent metadata

Field	Value
Publication number	US-10577307-B2
Application number	US-201716304429-A
Country	US
Kind code	B2
Filing date	Jun 1, 2017
Priority date	Jun 3, 2016
Publication date	Mar 3, 2020
Grant date	Mar 3, 2020

Abstract

A task is to provide a method for producing a polycyclic aromatic aminophenol compound through a reduced number of steps at a low cost with high safety. The method for producing a polycyclic aromatic aminophenol compound includes the step of reacting a compound represented by the general formula (1) below and an aromatic amino compound with each other:

Wherein n represents an integer of 1 to 8, Ar represents a benzene ring optionally having a substituent, or a naphthalene ring optionally having a substituent, each of R 1 and R 2 independently represents a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms and optionally having a substituent, or an aromatic group optionally having a substituent, and R 3 represents a hydroxyl group, a methoxy group, or a halogen atom.

First claim

The invention claimed is:

1. A method for producing a resin composition, the method comprising:
the step of reacting a compound represented by the general formula (1) and an aromatic amino compound with each other to produce a compound represented by the general formula (2); and
the step of adding a thermosetting resin to the compound represented by the general formula (2)

wherein
n represents an integer of 1 to 8,
Ar represents a benzene ring optionally having a substituent, or a naphthalene ring optionally having a substituent,
each of R 1 and R 2 independently represents a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms and optionally having a substituent, or an aromatic group optionally having a substituent, and
R 3 represents a hydroxyl group, a methoxy group, or a halogen atom;

wherein n, Ar, R 1 , and R 2 are as defined above,
p represents an integer of 1 to 7,
A represents a structure having one or more benzene rings,
Y 1 represents a direct bond or a divalent linking group, and
m represents an integer of 1 to 8.

2. A polycyclic aromatic aminophenol compound which is any one of the compounds represented by the following formulae (4-1) to (4-7), (4-10), and (4-12) to (4-19)

3. A method for producing a polycyclic aromatic aminophenol compound, the method comprising the step of reacting a compound represented by the general formula (1) below and an aromatic amino compound with each other to produce a compound represented by the general formula (2) below:

wherein
n represents an integer of 1 to 8,
Ar represents a benzene ring optionally having a substituent, or a naphthalene ring optionally having a substituent,
R 1 and R 2 are a hydrogen atom, and
R 3 is a hydroxyl group;

wherein n, Ar, R 1 , and R 2 are as defined above,
p represents an integer of 1 to 7,
A represents a structure having one or more benzene rings,
Y 1 represents a direct bond or a divalent linking group, and
m represents an integer of 1 to 8; and
wherein the reaction in the step uses no catalyst.

4. A resin composition comprising a polycyclic aromatic aminophenol compound which is any one of the compounds represented by the following formulae (4-1) to (4-19):

and a thermosetting resin.

5. The resin composition according to claim 4 , wherein the thermosetting resin is an epoxy resin and/or a maleimide resin.

6. A cured product comprising a product obtained by curing the resin composition according to claim 4 .

7. A cured product comprising a product obtained by curing the resin composition according to claim 5 .

Assignees

• Dainippon Ink & Chemicals

Inventors

• Arita Kazuo
• Shimono Tomohiro
• Yamaguchi Junji

Classifications

• C07C215/76

  of the same non-condensed six-membered aromatic ring · CPC title

• C07C215/80

  containing at least two amino groups bound to the carbon skeleton · CPC title

• C08G59/50

  Amines · CPC title

• C08G59/623 Primary

  Aminophenols · CPC title

• C07C217/90

  the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers · CPC title