# US 8,541,516 B2 · Phosphorus-containing compounds useful for making halogen-free, ignition-resistant polymers

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- Number: US 8,541,516 B2
- Document ID: US8541516B2
- Status: Granted
- Kind: B2
- Application number: 13/396,924
- Filed: 2012-02-15
- Published: 2012-06-07
- Granted: 2013-09-24
- Earliest claimed: 2006-10-20
- Assignees: Dow Global Technologies LLC
- Applicants: Joseph Gan
- Inventors: Joseph Gan
- Web page: https://patentgrep.com/patent/US8541516B2

## CPC

- C08L 61/00: Compositions of condensation polymers of aldehydes or ketones (with polyalcohols C08L59/00; with polynitriles C08L77/00); Compositions of derivatives of such polymers
- C07F 9/657172: {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)}
- C08G 59/1488: {containing phosphorus}
- C08G 59/304: {containing phosphorus}
- C08G 59/3254: {containing atoms other than carbon, hydrogen, oxygen or nitrogen}
- C08G 79/04: Phosphorus linked to oxygen or to oxygen and carbon
- C08K 5/53: bound to oxygen and to carbon only
- C08K 5/5313: Phosphinic compounds, e.g. R2=P(:O)OR'
- C08L 61/14: Modified phenol-aldehyde condensates
- C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L 63/04: Epoxynovolacs
- C09K 21/12: containing phosphorus
- C09K 21/14: Macromolecular materials
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## 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

### Claim 1

A process for making a curable phosphorus-containing, benzoxazine ring-containing resin composition comprising blending:
(1) a benzoxazine ring-containing compound comprising the reaction product of:
(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, or amine;
X is a hydrocarbylene group;
R″ is a hydrocarbyl group having from 1 to 8 carbon atoms;
p each independently represents a number from 1 to 4; and
a and b each independently represent a number equal to or greater than zero
(II) an amine compound when the Y functional group of Component (B) is hydroxyl, or a hydroxyl group-containing compound with the Y functional group is an amine; and
(III) an aldehyde compound; and
(2) a thermosetting composition.

### Claim 2 (depends on 1)

A process in accordance with claim 1 further comprising blending at least one inhibitor.

### Claim 3 (depends on 1)

A process in accordance with claim 1 further comprising blending at least one catalyst.

### Claim 4 (depends on 1)

A process in accordance with claim 1 wherein said thermosetting composition is selected from the group consisting of epoxies resin, polyurethanes, polyisocyanates, benzoxazine ring-containing compounds, unsaturated resin systems containing double or triple bonds, polycyanate esters, bismaleimides, triazines resin, and mixtures thereof.

### Claim 5 (depends on 2)

A process in accordance with claim 2 wherein said inhibitor is selected from the group consisting of boric acid, maleic acid, metaboric acid, boric anhydride, and combinations thereof.

### Claim 6 (depends on 3)

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.