Phosphorus-containing compound and curing epoxy resin composition containing same

Patent metadata

Field	Value
Publication number	US-2016200747-A1
Application number	US-201414915766-A
Country	US
Kind code	A1
Filing date	Nov 10, 2014
Priority date	Oct 1, 2013
Publication date	Jul 14, 2016
Grant date	—

Abstract

Provided is a novel phosphorus-containing compound represented by general formula (I). The compound has reactivity with a glycidyl group and is therefore capable of providing a curing epoxy resin composition that is expected to achieve flame retardation and reduction of dielectric constant.

wherein m is a number of 1 to 10; R 1 , R 2 , R 3 , and R 4 are each hydrogen, alkyl, or aryl; R 5 is alkyl, alkanediyl, alkanetriyl, alkanetetrayl, or an aromatic group; X is oxygen or sulfur; Y is oxygen, sulfur, or ═NR′; and R′ is hydrogen, alkyl, or aryl.

First claim

1 . A phosphorus-containing compound represented by general formula (I):

wherein m represents a number of 1 to 10; R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, an alkyl group, or an aryl group; R 5 represents an alkyl group, an alkanediyl group, an alkanetriyl group, an alkanetetrayl group, or an aromatic group; X represents an oxygen atom or a sulfur atom; Y represents an oxygen atom, a sulfur atom, or —NR′; and R′ represents a hydrogen atom, an alkyl group, or an aryl group.

2 . The phosphorus-containing compound according to claim 1 , wherein the aromatic group as represented by R 5 is represented by any one of formulae (1) through (9):

wherein n represents an integer of 1 to 4,

wherein R 6 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; o represents an integer of 1 to 3; p represents an integer of 0 to 50;
Z represents

wherein R 1 , R 2 , R 3 , R 4 , X, and Y are as defined above;
R 7 represents

wherein R 8 and R 9 each represent a hydrogen atom, CH 3 , or CF 3 ,

wherein t represents an integer of 4 to 12,

wherein R 10 represents a hydrogen atom or CH 3 ; and R 1 , R 2 , R 3 , R 4 , X, and Y are as defined above,

wherein q represents an integer of 0 to 50, and Z is as defined above, and

wherein r represents an integer of 0 to 25, and s represents an integer of 0 to 25, provided that the sum of r and s is 5 to 50; and Z is as defined above.

3 . The phosphorus-containing compound according to claim 1 , wherein R 1 , R 2 , R 3 , and R 4 each independently represent an alkyl group having 1 to 5 carbon atoms, R 5 represents an aromatic group represented by any one of formulae (1) to (9), and X and Y each represent an oxygen atom.

4 . A process comprising causing the phosphorus-containing compound according to claim 1 to react with an epoxy compound in accordance with reaction scheme:

wherein m represents a number of 1 to 10; R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, an alkyl group, or an aryl group; R 5 represents an alkyl group, an alkanediyl group, an alkanetriyl group, an alkanetetrayl group, or an aromatic group; X represents an oxygen atom or a sulfur atom; Y represents an oxygen atom, a sulfur atom, or ═NR 6 ; R 6 represents a hydrogen atom, an alkyl group, or an aryl group; and Ar represents an aromatic group.

5 . An epoxy resin curing agent comprising the phosphorus-containing compound according to claim 1 .

6 . A curing epoxy resin composition comprising the epoxy resin curing agent according to claim 5 .

7 . The phosphorus-containing compound according to claim 2 , wherein R 1 , R 2 , R 3 , and R 4 each independently represent an alkyl group having 1 to 5 carbon atoms, R 5 represents an aromatic group represented by any one of formulae (1) to (9), and X and Y each represent an oxygen atom.

8 . A process comprising causing the phosphorus-containing compound according to claim 2 to react with an epoxy compound in accordance with reaction scheme:

wherein m represents a number of 1 to 10; R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, an alkyl group, or an aryl group; R 5 represents an alkyl group, an alkanediyl group, an alkanetriyl group, an alkanetetrayl group, or an aromatic group; X represents an oxygen atom or a sulfur atom; Y represents an oxygen atom, a sulfur atom, or ═NR 6 ; R 6 represents a hydrogen atom, an alkyl group, or an aryl group; and Ar represents an aromatic group.

9 . A process comprising causing the phosphorus-containing compound according to claim 3 to react with an epoxy compound in accordance with reaction scheme:

wherein m represents a number of 1 to 10; R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, an alkyl group, or an aryl group; R 5 represents an alkyl group, an alkanediyl group, an alkanetriyl group, an alkanetetrayl group, or an aromatic group; X represents an oxygen atom or a sulfur atom; Y represents an oxygen atom, a sulfur atom, or ═NR 6 ; R 6 represents a hydrogen atom, an alkyl group, or an aryl group; and Ar represents an aromatic group.

10 . A process comprising causing the phosphorus-containing compound according to claim 7 to react with an epoxy compound in accordance with reaction scheme:

wherein m represents a number of 1 to 10; R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, an alkyl group, or an aryl group; R 5 represents an alkyl group, an alkanediyl group, an alkanetriyl group, an alkanetetrayl group, or an aromatic group; X represents an oxygen atom or a sulfur atom; Y represents an oxygen atom, a sulfur atom, or ═NR 6 ; R 6 represents a hydrogen atom, an alkyl group, or an aryl group; and Ar represents an aromatic group.

11 . An epoxy resin curing agent comprising the phosphorus-containing compound according to claim 2 .

12 . An epoxy resin curing agent comprising the phosphorus-containing compound according to claim 3 .

13 . An epoxy resin curing agent comprising the phosphorus-containing compound according to claim 7 .

Assignees

• Adeka Corp

Inventors

• Endo Takeshi
• Matsumoto Kozo
• Tamaso Ken-Ichi
• Ogawa Ryo

Classifications

• C08G59/446

  Phosphoramides · CPC title

• C07F9/2404

  the ester moiety containing a substituent or a structure which is considered as characteristic · CPC title

• C08G59/4071

  phosphorus containing compounds · CPC title

• C07F9/242 Primary

  of hydroxyaryl compounds · CPC title

• C08G59/1488

  containing phosphorus · CPC title