# US 4,394,306 A · Bromine containing fire retardant compositions of matter

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- Number: US 4,394,306 A
- Document ID: US4394306A
- Status: Granted
- Kind: A
- Application number: 06/256,476
- Filed: 1981-04-22
- Granted: 1983-07-19
- Earliest claimed: 1980-05-23
- Assignees: Imi Tami Institute for Research and Development Ltd.
- Inventors: Manny Ravey
- Web page: https://patentgrep.com/patent/US4394306A

## CPC

- C07C 41/50: by reactions producing [IMAGE cpc-sch-C07C-0958.gif] groups
- C08K 5/06: Ethers; Acetals; Ketals; Ortho-esters
- Y10S 428/921: Fire or flameproofing
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

The present invention relates to novel fire retardant compositions, based on the compounds 2-bromomethyl-2-hydroxy-methylpropane-1,3-diol, 2,2-bis(bromomethyl)propane-1,3-diol, 2-bromomethyl-2-hydroxymethyl-1,3-dibromopropane, and mixtures thereof, the compositions having a general formula (BrCH.sub.2).sub.m C[CH.sub.2 O(CH.sub.2 O).sub.x H].sub.4-m wherein m is between 1.6 to 2.3 and x is between 0.75 to 1.10. These compositions are characterized by their particular infra-red spectra. The novel fire retardant compositions are produced by the reaction of formaldehyde or its polymeric forms with the above compounds, followed by the removal of water from the reaction system. The fire retardant compositions according to the present invention are suitable as active or additive fire retardant ingredients for various polymeric materials, such as polyurethane, polyester or epoxide resins.

## Claims

### Claim 1

A composition of matter of the formula
(BrCH.sub.2).sub.m C[CH.sub.2 O(CH.sub.2 O).sub.x H].sub.4-m
wherein m=1.6 to 2.3 and x=0.75 to 1.10, obtained by the hydroxymethylation 2-bromomethyl-2-hydroxymethyl-propane-1,3-diol, 2,2-bis(bromomethyl)propane-1,3-diol, 2-bromomethyl-2-hydroxymethyl-1,3-dibromopropane, and mixtures thereof, containing an average of 1.7 to 2.5 hydroxyl groups per molecule, with formaldehyde or its polymeric forms, said compositions of matter being useful as active or additive fire retardants for polymeric materials.

### Claim 2 (depends on 1)

A composition of matter according to claim 1, wherein m=2 and x is between 1.0 to 1.1.

### Claim 3 (depends on 1)

A composition of matter according to claim 1, wherein m=2 and x=0.75.

### Claim 4 (depends on 1)

A composition of matter according to claim 1, wherein the infra-red spectra of said composition show a very broad and strong absorption band within the range of 950 to 1150 cm.sup.-1 with maximum at 1130 cm.sup.-1, 1040 to 1050 cm.sup.-1 and 1010 cm.sup.-1, along with two weak bands at 840 cm.sup.-1 and 870 cm.sup.-1.

### Claim 5

A method for the manufacture of compositions of matter having the formula (Br CH.sub.2).sub.m C[CH.sub.2 (CH.sub.2 O).sub.x H].sub.4-m wherein m=1.6 to 2.3 and x=0.75 to 1.10, which consists in the substitution of the hydrogen atom of the alcoholic hydroxyl group by --CH.sub.2 OH group by the reaction of equivalent amounts of aqueous solutions of formaldehyde or its polymeric forms with 2-bromomethyl-2-hydroxymethylpropane-1,3-diol, 2,2-bis(bromomethyl)propane-1,3-diol, 2-bromomethyl-2-hydroxymethyl-1,3-dibromopropane, and mixtures thereof, followed by removal of water from the reaction system.

### Claim 6 (depends on 5)

A method for the manufacture of compositions according to claim 5, wherein the amount of formaldehyde is less than the equivalent, thus producing the compositions of formula (BrCH.sub.2).sub.m C[CH.sub.2 O(CH.sub.2 O).sub.x H].sub.4-m wherein m=2 and x=0.75.

### Claim 7 (depends on 5, 6)

The method for the manufacture of compositions according to claim 5 or 6, wherein the brominated reactant consists of a mixture of 5% 2-dibromomethyl-2-hydroxymethylpropane-1,3-diol, 80% 2:2-bis(bromomethyl)-propane-1,3-diol and 15% 2-bromomethyl-2-hydroxymethyl-1,3-dibromopropane.

### Claim 8 (depends on 5, 6)

A method for the manufacture of compositions according to claim 5 or 6, wherein the brominated reactant consists of a mixture of 15% 2-bromomethyl-2-hydroxymethylpropane-1,3-diol, 80% 2,2-bis(bromomethyl)propane-1,3-diol and 5% 2-bromomethyl-2-hydroxymethyl-1,3-dibromopropane.

### Claim 9 (depends on 5, 6)

A method according to claim 5 or 6, wherein the reaction between formaldehyde or its polymeric forms and said composition is carried out at temperatures of above approximately 40.degree. C.

### Claim 10 (depends on 5)

A method according to claim 5, wherein water is expelled from the reaction vessel by applying vacuum.

### Claim 11 (depends on 1)

Fire retardant compositions comprising compounds, according to claim 1, together with phosphorus-containing reactive fire retardant component.

### Claim 12 (depends on 1)

Fire retardant compositions comprising compounds, according to claim 1, together with O,O-diethyl-N,N-bis-(2-hydroxyethyl)aminomethylphosphonate.

### Claim 13 (depends on 11, 12)

Fire retardant compositions according to claim 11 or 12, applied to a polymeric substrate consisting of polyurethane.

### Claim 14 (depends on 11, 12)

Fire retardant compositions according to claim 11 or 12, applied to a polymeric substrate consisting of polyester.

### Claim 15 (depends on 11, 12)

Fire retardant compositions according to claim 11 or 12, applied to a polymeric substrate consisting of epoxide.