Flame retardants, processes for their preparation and uses thereof in polyurethane and polyisocyanurate foams

Patent metadata

Field	Value
Publication number	US-9309377-B2
Application number	US-201414247574-A
Country	US
Kind code	B2
Filing date	Apr 8, 2014
Priority date	Oct 9, 2011
Publication date	Apr 12, 2016
Grant date	Apr 12, 2016

Abstract

The invention provides pentabromobenzyl moiety containing hydroxy-functional compounds which are useful as flame-retardants in flexible and rigid polyurethane foams and also in rigid polyisocyanurate foams. Processes for preparing the compounds, polyurethane and polyisocyanurate foams containing the compounds are also provided by the invention.

First claim

The invention claimed is:

1. A compound of Formula 1:

wherein each of n 1 and n 2 is an integer equal to or greater than 1, with the sum (n 1 +n 2 ) being equal to or greater than 3, and Z is a moiety derived from a branched polyol containing n chains, with n=n 1 +n 2 , wherein each chain comprises not less than 3 repeating units, wherein the repeating unit is an alkylene oxide unit or [CO—(C 2 -C 5 )alkylene-O] unit.

2. The compound according to claim 1 ,
wherein the chains are selected from the group consisting of:
O—[(C 2 -C 3 )alkylene-O] m —(C 2 -C 3 )alkylene and O—[CO—(C 2 -C 5 )alkylene-O] m —(C 2 -C 5 )alkylene, m≧3, and n is an integer from 3 to 6.

3. The compound according to claim 2 , wherein n=3 and the chains are O—[(C 2 -C 3 )alkylene-O] m —(C 2 -C 3 )alkylene.

4. The compound according to claim 3 , wherein the chains are O—[CH 2 —CH 2 —O] m —CH 2 —CH 2 —.

5. The compound according to claim 3 , wherein the chains are O—[CH 2 —CH(CH 3 )—O] m —CH 2 —CH(CH 3 )—.

6. The compound according to claim 4 , having three chains, wherein two chains are terminated with pentabromobenzyl group and one chain is terminated with hydroxyl group, said compound being represented by the following formula:
CH 2 —O—[CH 2 —CH 2 —O] m —CH 2 —CH 2 —O—CH 2 —C 6 Br 5 .

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CH—O—[CH 2 —CH 2 —O] m —CH 2 —CH 2 —O—CH 2 —C 6 Br 5 .

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CH 2 —O—[CH 2 —CH 2 —O] m —CH 2 —CH 2 —OH.

7. A mixture comprising two or more compounds of claim 1 , wherein in a first compound n 1 ≧n 2 and in a second compound n 1 <n 2 .

8. A process for preparing the compound of Formula 1 as defined in claim 1 , comprising reacting pentabromobenzyl halide with branched polyol of the formula Z(OH)n, which contains n chains with n terminal hydroxyl groups wherein n≧3, optionally in the presence of a base, and forming the compound of Formula 1 as defined in claim 1 .

9. The process according to claim 8 , wherein the pentabromobenzyl halide is pentabromobenzyl bromide, said process being carried out in the presence of a base which is either sodium hydroxide, potassium hydroxide or a mixture thereof.

10. The process according to claim 8 , wherein the branched polyol Z(OH)n has a molecular weight of between 250 and 3000 Da.

11. The process according to claim 10 , wherein the branched polyol Z(OH)n comprises glycerol-based polyether polyol.

12. The process according to claim 11 , wherein the glycerol-based polyether polyol is selected from the group consisting of glycerol-ethoxylated polyether polyol and glycerol-propoxylated polyether polyol.

13. A process, comprising charging a reaction vessel with a branched polymeric polyol, a base and an organic solvent, heating the reaction mixture under reflux to remove water therefrom, adding pentabromobenzyl halide to the reaction mixture, maintaining heating and stirring to complete the reaction, and collecting the compound of Formula 1 as defined in claim 1 .

14. A flame retardant composition comprising the compound(s) of Formula 1 as defined in claim 1 and at least one ester of phosphoric acid.

15. The flame retardant composition according to claim 14 , which further comprises tribromoneopentyl alcohol.

16. A polyurethane or polyisocyanurate composition flame-retarded with the compound of Formula 1 as defined in claim 1 .

17. The polyurethane or polyisocyanurate composition according to claim 16 , wherein the polyurethane or polyisocyanurate composition is selected from the group consisting of flexible polyurethane foam, rigid polyurethane foam and polyisocyanurate foam.

18. Flexible polyurethane foams flame-retarded with the compound of Formula 1 as defined in claim 1 .

19. Rigid polyurethane foams flame-retarded with the compound of Formula 1 as defined in claim 1 .

20. Polyisocyanurate foams flame-retarded with the compound of Formula 1 as defined in claim 1 .

Assignees

• Bromine Compounds Ltd

Inventors

• Gelmont Mark
• Yuzefovich Michael
• Peled Dorit
• Cohen Orly
• Frim Ron

Classifications

• C08G18/6618

  with compounds of group C08G18/3225 or polyamines of C08G18/38 · CPC title

• C08G18/6674

  with compounds of group C08G18/3203 · CPC title

• C08G18/4804

  Two or more polyethers of different physical or chemical nature · CPC title

• C08G18/7664

  containing alkylene polyphenyl groups · CPC title

• C07C43/1786

  containing halogen · CPC title