Phosphorous containing compounds and process for synthesis

Patent metadata

Field	Value
Publication number	US-9546262-B1
Application number	US-201514932092-A
Country	US
Kind code	B1
Filing date	Nov 4, 2015
Priority date	Nov 4, 2015
Publication date	Jan 17, 2017
Grant date	Jan 17, 2017

Abstract

The instant disclosure relates to phosphorus-containing compounds that can be used to form flame retardant phosphorus-containing resins, and also can serve as a hardener for a flame retardant epoxy resin compositions. In particular, the phosphorus-containing compounds are modified with acyloxy groups (—O—(C═O)—R), as shown below. Incorporation of the acyloxy groups results in resins that are water resistant and exhibit improved dielectric properties.

First claim

The invention claimed is:

1. A compound of Formula (II)

wherein,
n′ is an integer from 1 to 4;
R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of H, C 1 -C 10 alkyl, C 1 -C 10 alkoxy, and C 3 -C 10 cycloalkyl;
R 5 is independently selected from the group consisting of H, C 1 -C 10 alkyl, C 1 -C 10 alkoxy, C 3 -C 10 cycloalkyl, and Ar a ; and
Ar 1 and Ar 2 are independently selected from the group consisting of

Ar 3 is selected from the group consisting of

R 6 and R 7 are independently selected from the group consisting of H, C 1 -C 10 alkyl group, C 1 -C 10 alkoxy, and a cyclic alkyl group having 3-10 carbon atoms,
m and n are independently an integer from 0 to 4;
R 8 is absent or is selected from the group consisting of —CH 2 —, —(CH 3 ) 2 C—, —CO—, —SO 2 —, and —O—
R 9 is absent or is —(CH 2 ) p , wherein p is an integer from 1 to 20;
z is 1;
A is selected from the group consisting of C 1 -C 10 alkyl,

wherein, each R 10 is independently H or C 1 -C 10 alkyl; and
x is an integer from 0 to 4; and
Ep is selected from the group consisting of:

wherein each of R 11 is independently selected from the group consisting of H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, a cyclic alkyl group having 3-7 carbon atoms, phenyl, and a phenoxyl group.

2. The compound of claim 1 , wherein each of R 11 is independently H or a C 1 -C 6 alkyl.

3. The compound of claim 1 , wherein Ep is selected from the group consisting of:

4. The compound of claim 3 , wherein R 9 is absent.

5. The compound of claim 1 , wherein R 5 is H.

6. The compound of claim 1 , wherein R 5 is C 1 -C 10 alkyl.

7. The compound of claim 1 , wherein R 5 is methyl.

8. The compound of claim 1 , wherein Ar 1 and Ar 2 are

9. The compound of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are H.

10. The compound of claim 1 , wherein
R 1 , R 2 , R 3 and R 4 are H;
R 5 is C 1 -C 10 alkyl;
Ar 1 and Ar 2 are

and
R 11 is H.

11. The compound of claim 10 , wherein Ep is selected from the group consisting of:

12. The compound of claim 11 , wherein R 9 is absent.

13. A method for synthesizing a compound of Formula (II)

wherein,
n′ is an integer from 1 to 4;
R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of H, C 1 -C 10 alkyl, C 1 -C 10 alkoxy, C 3 -C 10 cycloalkyl;
R 5 is independently selected from the group consisting of H, C 1 -C 10 alkyl, C 1 -C 10 alkoxy, and C 3 -C 10 cycloalkyl, and Ar a ; and
Ar 1 and Ar 2 are independently selected from the group consisting of

Ar 3 is selected from the group consisting of

R 6 and R 7 are independently selected from the group consisting of H, C 1 -C 10 alkyl group, C 1 -C 10 alkoxy, and a cyclic alkyl group having 3-10 carbon atoms,
m and n are independently an integer from 0 to 4;
R 8 is absent or is selected from the group consisting of —CH 2 —, —(CH 3 ) 2 C—, —CO—, —SO 2 —, and —O—
R 9 is absent or is —(CH 2 ) p , wherein p is an integer from 1 to 20;
z is 1;
A is selected from the group consisting of C 1 -C 10 alkyl,

wherein, each R 10 is independently H or C 1 -C 10 alkyl; and
x is an integer from 0 to 4; and
Ep is selected from the group consisting of:

wherein each of R 11 is independently selected from the group consisting of H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, a cyclic alkyl group having 3-7 carbon atoms, phenyl, and a phenoxyl group;
comprising performing a catalytic reaction of a compound of formula (I)

with an epoxy monomer of formula (III)

14. The method of claim 13 , wherein each of R 11 is independently H or a C 1 -C 6 alkyl.

15. The method of claim 13 , wherein Ep is selected from the group consisting of:

16. The method of claim 13 , wherein R 5 is H.

17. The method of claim 13 , wherein R 5 is C 1 -C 10 alkyl.

18. The method of claim 13 , wherein R 5 is methyl.

19. The method of claim 13 , wherein Ar 1 and Ar 2 are

20. A compound selected from the group consisting of:

wherein n′ is an integer from 1 to 4.

Assignees

• Chang Chun Plastics Co Ltd

Inventors

• Tu An-Pang
• Chen Szu-Fang
• Wang Ping-Chieh
• Hwang Kuen-Yuan

Classifications

• C07F9/65744 Primary

  condensed with carbocyclic or heterocyclic rings or ring systems · CPC title

• C08K5/5313 Primary

  Phosphinic compounds, e.g. R2=P(:O)OR' · CPC title

• C08J5/244 Primary

  using glass fibres · CPC title

• C07F9/657172

  the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: [IMAGE cpc-sch-C07F-1008.gif] (X = O, S) · CPC title

• C09K21/12

  containing phosphorus · CPC title