Brominated flame retardants and polyurethanes containing the same

Patent metadata

Field	Value
Publication number	US-12378380-B2
Application number	US-201917418307-A
Country	US
Kind code	B2
Filing date	Dec 20, 2019
Priority date	Dec 27, 2018
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

The disclosure includes brominated alkenyl alcohols, their use as a flame retardant in polyurethane and polyurethane foams, and polyurethanes containing the brominated alkenyl alcohols. Compositions, methods, and processes are disclosed. The brominated alkenyl alcohols used as flame retardants in polyurethanes can be generally described by Formula (I), the scope of which is disclosed herein.

First claim

We claim:

1. A polyurethane prepared by reacting at least one isocyanate and/or polyisocyanate and a compound of Formula 1,

wherein
X 1 and X 2 are each independently H, Cl, or Br, and at least one of X 1 or X 2 is Br;
R 1 is H, Cl, Br, C 1 -C 4 alkyl, or —(CR 5 R 6 ) m —OR 7 ;
R 2 is a C 2 -C 8 alkylhydroxyl;
R 3 , R 4 , R 5 and R 6 are each independently H, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 1 -C 8 haloalkyl or C 2 -C 8 haloalkenyl;
R 7 is H, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 1 -C 8 haloalkyl, or C 2-8 haloalkenyl;
n=1-4;
m=1-4; and
the compound of Formula 1 is chemically bonded in the polyurethane foam through at least one hydroxyl group on the compound.

2. The polyurethane of claim 1 , wherein R 1 is H.

3. The polyurethane of claim 1 , wherein n is 1 and m, when present, is 1.

4. The polyurethane of claim 1 , wherein X 1 is Br and X 2 is Cl or H.

5. The polyurethane of claim 1 , wherein X 1 is Br, X 2 is H, and R 1 is H.

6. The polyurethane of claim 1 , wherein X 1 , X 2 and R 1 are each Br.

7. The polyurethane of claim 1 , wherein n is 2-4.

8. The polyurethane of claim 1 , wherein R 1 is H, and one of X 1 and X 2 is Br, while the other is Cl.

9. The polyurethane of claim 1 , wherein one of X 1 and X 2 is Br, while the other is H.

10. The polyurethane of claim 1 , wherein the compound of Formula 1 is:

11. A formulation comprising a compound of Formula I and at least one polyol,

wherein
X 1 and X 2 are each independently H, Cl, or Br, and at least one of X 1 or X 2 is Br;
R 1 is H, Cl, Br, C 1 -C 4 alkyl, or —(CR 5 R 6 ) m —OR 7 ;
R 2 is a C 2 to C 8 alkylhydroxyl;
R 3 , R 4 , R 5 and R 6 are each independently H, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 1 -C 8 haloalkyl or C 2 -C 8 haloalkenyl;
R 7 is H, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 1 -C 8 haloalkyl, or C 2-8 haloalkenyl;
n=1-4; and
m=1-4.

12. The formulation of claim 11 , wherein R 1 is H.

13. The formulation of claim 11 , wherein n is 1 and m, when present, is 1.

14. The formulation of claim 11 , wherein X 1 is Br and X 2 is Cl or H.

15. The formulation of claim 11 , wherein X 1 is Br, X 2 is H, and R 1 is H.

16. The formulation of claim 11 , wherein X 1 , X 2 and R 1 are each Br.

17. The formulation of claim 11 , wherein the compound of Formula 1 is:

18. The formulation of claim 11 , further comprising a blowing agent.

Assignees

• Albemarle Corp

Inventors

• Ibay Augusto C
• Wu Tse-Chong
• Varnado Jr Charles D
• Liu Yunqi

Classifications

• C08J2375/12

  from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group · CPC title

• C08J2203/182

  of physical blowing agents, e.g. acetone and butane · CPC title

• C08J2203/162

  Halogenated unsaturated hydrocarbons, e.g. H2C=CF2 · CPC title

• C08J2203/10

  Water or water-releasing compounds · CPC title

• C08J9/146

  only fluorine as halogen atoms · CPC title