Preparation of bromine-containing polymers useful as flame retardants

Patent metadata

Field	Value
Publication number	US-10336858-B2
Application number	US-201515323847-A
Country	US
Kind code	B2
Filing date	Jul 7, 2015
Priority date	Jul 8, 2014
Publication date	Jul 2, 2019
Grant date	Jul 2, 2019

Abstract

The invention relates to a process for preparing bromine-containing polymer, comprising a Friedel-Crafts alkylation reaction of tetrabromoxylylene dihalide, or tetrabromoxylylene dihalide in combination with pentabromobenzyl halide, with a reactant having one or more six-membered aromatic rings, wherein the reaction takes place in a solvent in the presence of a Friedel-Crafts catalyst, and isolating from the reaction mixture the bromine-containing polymer. The so-formed polymers and their use as flame retardants form additional aspects of the invention.

First claim

The invention claimed is:

1. A process for preparing bromine-containing polymer, comprising a Friedel-Crafts alkylation reaction of tetrabromoxylylene dihalide, or tetrabromoxylylene dihalide in combination with pentabromobenzyl halide, with a reactant having one or more six-membered aromatic rings of Formula (II):

where R is a linear or branched aliphatic chain; k is an integer from 0 to 3; m is 0 or 1; and Z is selected from the group consisting of null, O, S and a linear or branched alkylene, wherein the reaction takes place in a solvent in the presence of a Friedel-Crafts catalyst, and isolating from the reaction mixture the bromine-containing polymer of Formula (I):

wherein R, k, m, and Z are as defined above; each of a1 and a2 is independently an integer from 1 to 3; and each of b1 and b2 is independently an integer from 1 to 3, such that a1+b1≤3 and a2+b2≤3.

2. A process according to claim 1 , wherein a combination of tetrabromoxylylene dihalide and pentabromobenzyl halide is used.

3. A process according to claim 1 , wherein the tetrabromoxylylene dihalide is tetrabromo-para-xylylene dibromide and the pentabromobenzyl halide is pentabromobenzyl bromide.

4. A process according to claim 1 , wherein the reactant is a compound of Formula II selected from the group consisting of:
toluene, where in Formula II, R=CH 3 , k=1, m=0;
xylene, where in Formula II, R=CH 3 , k=2, m=0;
ethylbenzene, where in Formula II, R=C 2 H 5 , k=1, m=0;
diphenyl ether, where in Formula II, k=0, Z=O, m=1;
diphenylmethane, where in Formula II, k=0, Z=—CH 2 —, m=1; and
1,2-diphenylethane, wherein in Formula II, k=0, Z=—(CH 2 ) 2 —, m=1.

5. A process according to claim 4 , comprising reacting toluene with tetrabromo-para-xylylene dibromide and pentabromobenzyl bromide in halogenated aliphatic hydrocarbon solvent to give a bromine-containing polymer comprising chains of Formula III (where n indicates the number of repeat units):

6. A process according to claim 4 , comprising reacting1,2-diphenylethane with tetrabromo-para-xylylene dibromide and pentabromobenzyl bromide in halogenated aliphatic hydrocarbon solvent to give a bromine-containing polymer comprising chains of Formula V (wherein n indicates the number of repeat units):

Assignees

• Bromine Compounds Ltd

Inventors

• Gelmont Mark
• Yuzefovich Michael
• Piotrowski Andrew
• Yoffe David
• Frim Ron
• Hirschsohn Yaniv

Classifications

• C09K21/14

  Macromolecular materials · CPC title

• C08L55/02

  ABS [Acrylonitrile-Butadiene-Styrene] polymers · CPC title

• C08L51/04

  grafted on to rubbers · CPC title

• C08G2261/45

  Friedel-Crafts-type · CPC title

• C08G2261/3424

  non-conjugated, e.g. paracyclophanes or xylenes · CPC title