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

Patent metadata

Field	Value
Publication number	US-9752010-B2
Application number	US-201615207225-A
Country	US
Kind code	B2
Filing date	Jul 11, 2016
Priority date	May 25, 2011
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

A process for making a phosphorus-containing compound is disclosed. The process comprises contacting a compound of formula (A) wherein R A and R B are selected from optionally substituted aryl, aryloxy, alkyl and alkoxy groups or can be combined to form cyclic structures; and R C is methyl, ethyl, isopropyl, n-butyl, i-butyl, t-butyl, phenyl or benzyl; and a compound of formula (B) wherein R 1 -R 4 are selected from optionally substituted aryl, aryloxy, alkyl and alkoxy groups. The phosphorus-containing compound can then be used as a flame retardants for polymers, especially for epoxy, polyurethane, thermosetting resins and thermoplastic polymers. Such flame retardant-containing polymers can be used to make protective coating formulations and ignition-resistant fabricated articles, such as electrical laminates, polyurethane foams, and various molded and/or foamed thermoplastic products.

First claim

What is claimed:

1. A process for making a curable phosphorus-containing epoxy resin composition comprising blending:
(I) a phosphorus-containing compound comprising the reaction product of:

wherein R A and R B , independently of one another, are selected from the group consisting of substituted aryl groups, substituted aryloxy groups, unsubstituted aryl groups, unsubstituted aryloxy groups, substituted alkyl groups, and unsubstituted alkyl groups;
or wherein R A and R B are be combined to form cyclic structures;
wherein R c is a hydrocarbyl radical containing in the range of from 1 to 12 carbon atoms per molecule and is selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, i-butyl, t-butyl, phenyl, and benzyl; and

wherein R 1 -R 4 , independently from one another, are selected from the group consisting of hydrogen, a substituted alkyl group, a substituted alkoxy group, an unsubstituted alkyl group, an unsubstituted alkoxy group, a substituted aryl group, a substituted aryloxy group, an unsubstituted aryl group and an unsubstituted aryloxy group;
(II) at least one epoxy resin; and
(III) at least one catalyst.

2. A phosphorus-containing compound prepared by a process comprising contacting:

wherein R A and R B , independently of one another, are selected from the group consisting of substituted aryl groups, substituted aryloxy groups, unsubstituted aryl groups, unsubstituted aryloxy groups, substituted alkyl groups, and unsubstituted alkyl groups;

or wherein R A and R B are be combined to form cyclic structures;
wherein R C is a hydrocarbyl radical containing in the range of from 1 to 12 carbon atoms per molecule and is selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, i-butyl, t-butyl, phenyl, and benzyl; and

wherein R 1 -R 4 , independently from one another, are selected from the group consisting of hydrogen, a substituted alkyl group, a substituted alkoxy group, an unsubstituted alkyl group, an unsubstituted alkoxy group, a substituted aryl group, a substituted aryloxy group, an unsubstituted aryl group and an unsubstituted aryloxy group.

3. A phosphorus-containing compound prepared by a process comprising contacting:

wherein R 1 -R 4 , independently from one another, are selected from the group consisting of hydrogen, a substituted alkyl group, a substituted alkoxy group, an unsubstituted alkyl group, an unsubstituted alkoxy group, a substituted aryl group, a substituted aryloxy group, an unsubstituted aryl group and an unsubstituted aryloxy group.

4. A varnish produced from the composition of claim 1 .

5. A prepreg prepared from the varnish of claim 4 .

6. An electrical laminate prepared from the varnish of claim 4 .

7. A printed circuit board prepared from the varnish of claim 4 .

8. A coating prepared from the composition of claim 1 .

9. A composite prepared from the composition of claim 1 .

10. A casting prepared from the composition of claim 1 .

11. An adhesive prepared from the composition of claim 1 .

12. The process of claim 1 , wherein compound (B) is defined by the following formula:

13. The process of claim 1 , wherein compound (B) is defined by the following formula:

14. The process of claim 1 , wherein compound (B) is defined by the following formula:

Assignees

• Blue Cube Ip Llc

Inventors

• Worku Anteneh Z
• Mullins Michael J

Classifications

• C08K5/527

  Cyclic esters · CPC title

• C09J11/06

  organic · CPC title

• C07F9/657172 Primary

  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

• C07F9/657181

  the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative · CPC title

• C08J2363/04

  Epoxynovolacs · CPC title