# US 9,752,010 B2 · Phosphorus-containing compounds useful for making halogen-free, ignition-resistant polymers

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- Number: US 9,752,010 B2
- Document ID: US9752010B2
- Status: Granted
- Kind: B2
- Application number: 15/207,225
- Filed: 2016-07-11
- Published: 2016-11-03
- Granted: 2017-09-05
- Earliest claimed: 2011-05-25
- Assignees: Blue Cube IP LLC
- Applicants: Blue Cube IP LLC
- Inventors: Anteneh Z. Worku; Michael J. Mullins
- Web page: https://patentgrep.com/patent/US9752010B2

## CPC

- C08K 5/51: Phosphorus bound to oxygen
- C07F 9/28: with one or more P—C bonds
- 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)}
- C07F 9/657181: {the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative}
- C08J 5/249: {characterised by the additives used in the prepolymer mixture}
- C08K 5/527: Cyclic esters
- C08K 5/5313: Phosphinic compounds, e.g. R2=P(:O)OR'
- C08K 5/5393: Phosphonous compounds, e.g. R—P(OR')2
- C09D 163/04: Epoxynovolacs
- C09J 11/06: organic
- C09J 163/04: Epoxynovolacs
- H05K 1/0353: {consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement}
- C08J 2363/04: Epoxynovolacs
- C08K 5/0066: {Flame-proofing or flame-retarding additives}
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- H05K: PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS

## Abstract

A process for making a phosphorus-containing compound is disclosed. The process comprises contacting a compound of formula (A) wherein RA and RB are selected from optionally substituted aryl, aryloxy, alkyl and alkoxy groups or can be combined to form cyclic structures; and RC is methyl, ethyl, isopropyl, n-butyl, i-butyl, t-butyl, phenyl or benzyl; and a compound of formula (B) wherein R1-R4 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.

## Claims

### Claim 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 RA and RB, 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 RA and RB are be combined to form cyclic structures;
wherein Rc 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 R1-R4, 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.

### Claim 2

A phosphorus-containing compound prepared by a process comprising contacting:
wherein RA and RB, 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 RA and RB are be combined to form cyclic structures;
wherein RC 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 R1-R4, 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.

### Claim 3

A phosphorus-containing compound prepared by a process comprising contacting:
wherein R1-R4, 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.

### Claim 4 (depends on 1)

A varnish produced from the composition of claim 1.

### Claim 5 (depends on 4)

A prepreg prepared from the varnish of claim 4.

### Claim 6 (depends on 4)

An electrical laminate prepared from the varnish of claim 4.

### Claim 7 (depends on 4)

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

### Claim 8 (depends on 1)

A coating prepared from the composition of claim 1.

### Claim 9 (depends on 1)

A composite prepared from the composition of claim 1.

### Claim 10 (depends on 1)

A casting prepared from the composition of claim 1.

### Claim 11 (depends on 1)

An adhesive prepared from the composition of claim 1.

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 1)

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

### Claim 14 (depends on 1)

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