IP Library Granted Patent US 8,440,771
Granted Patent B2
US 8,440,771 · App. 13/354,511 · Granted May 14, 2013

Phosphorus-containing compounds useful for making halogen-free, ignition-resistant polymers

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Quick Facts
Patent No.
US 8,440,771
App. No.
13/354,511
Granted
May 14, 2013
Kind
B2
Abstract

Phosphorus-containing compounds useful for flame retardant epoxy resins are disclosed. The flame retardant epoxy resins may be used to make electrical laminates. This invention is particularly useful in end use applications in which a low bromine or low halogen content is required or desired.

Claims (32)

1. A process for making a curable phosphorus-containing epoxy resin composition comprising blending:

(I) a phosphorus-containing compound comprising the reaction product of:

(A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and

(B) at least one compound having the following Formula (V):

wherein

R1 each independently is hydrogen or an alkyl group having from 1 to 10 carbon atoms;

Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, and amine;

X is a hydrocarbylene group;

R″ is a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms;

p each independently represents a number from zero to 4; and

a and b each independently represent a number equal to or greater than zero; and

(II) at least one epoxy resin.

2. A process in accordance with claim 1 wherein the epoxy resin is selected from group consisting of a phenol epoxy novolac, a cresol epoxy novolac, a polyoxazolidone ring containing epoxy resin, a bromine free epoxy resin, a brominated epoxy resin, a phosphorous-containing epoxy resin, and mixtures thereof.

3. A process in accordance with claim 1 further comprising blending a catalyst.

4. A process in accordance with claim 3 wherein the catalyst is a compound selected from the group consisting of an amine-containing compound, a phosphine-containing compound, an ammonium-containing compound, a phosphonium-containing compound, an arsonium-containing compound, a sulfonium-containing compound, a heterocyclic nitrogen-containing compound and mixtures thereof.

5. A process in accordance with claim 4 wherein the catalyst is selected from the group consisting of benzyldimethylamine, tris-(dimethylaminomethyl)phenol, 1,8-diazabicyclo(5.4.0) undec-7-ene, 2-phenylimidazole, N-methylimidazole, 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole, 2-methylimidazole and mixtures thereof.

6. A process for making a curable phosphorus-containing epoxy resin composition comprising blending:

(I) a phosphorus-containing compound comprising the reaction product of:

(A) at least one organophosphorus compound having a group selected from the group H—P═O, the group P—H, and the group P—OH; and

(B) at least one compound having the following Formula (VI):

wherein

R1 each independently is hydrogen or an alkyl group having from 1 to 10 carbon atoms;

Y is a functional group selected from hydroxy, carboxylic acid, carboxylate, acid anhydride, and amine;

X is a hydrocarbylene group;

R″ is a hydrocarbyl group having from 1 to 8 carbon atoms, R is alkyl or aryl group having from 1 to 12 carbon atoms;

p each independently represents a number from zero to 4; and

a and b each independently represent a number equal to or greater than zero; and

(II) at least one epoxy resin.

7. A process in accordance with claim 6 wherein the epoxy resin is selected from group consisting of a phenol epoxy novolac, a cresol epoxy novolac, a polyoxazolidone ring containing epoxy resin, a bromine free epoxy resin, a brominated epoxy resin, a phosphorous-containing epoxy resin, and mixtures thereof.

8. A process in accordance with claim 6 further comprising blending a catalyst.

9. A process in accordance with claim 8 wherein the catalyst is a compound selected from the group consisting of an amine-containing compound, a phosphine-containing compound, an ammonium-containing compound, a phosphonium-containing compound, an arsonium-containing compound, a sulfonium-containing compound, a heterocyclic nitrogen-containing compound and mixtures thereof.

10. A process in accordance with claim 9 wherein the catalyst is selected from the group consisting of benzyldimethylamine, tris-(dimethylaminomethyl)phenol, 1,8-diazabicyclo(5.4.0) undec-7-ene, 2-phenylimidazole, N-methylimidazole, 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole, 2-methylimidazole and mixtures thereof.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 11, 2015
From: DOW GLOBAL TECHNOLOGIES LLC
To: BLUE CUBE IP LLC
Reel/Frame 035887/0193 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 11, 2014
From: GAN, JOSEPH
To: DOW DEUTSCHLAND GMBH & CO. OHG
Reel/Frame 033073/0642 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 11, 2014
From: DOW DEUTSCHLAND GMBH & CO. OHG
To: THE DOW CHEMICAL COMPANY
Reel/Frame 033073/0916 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 11, 2014
From: THE DOW CHEMICAL COMPANY
To: DOW GLOBAL TECHNOLOGIES INC.
Reel/Frame 033073/0971 →
CHANGE OF NAME Recorded Jun 11, 2014
From: DOW GLOBAL TECHNOLOGIES INC.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 033125/0595 →