Process for the production of brominated polyether polyols

Patent metadata

Field	Value
Publication number	US-10647813-B2
Application number	US-201515325216-A
Country	US
Kind code	B2
Filing date	Jul 10, 2015
Priority date	Jul 10, 2014
Publication date	May 12, 2020
Grant date	May 12, 2020

Abstract

The present invention relates to brominated polyether polyols, processes for the production as well as intermediates useful in the production of the same and to processes for the preparation of flame-retardant blends, premixes as well as polyurethane foams.

First claim

The invention claimed is:

1. A process for the production of a compound or a mixture of compounds according to general formula (I):

wherein R 1 and R 4 are independently selected from the group consisting of H, methyl, Cl and Br; R 2 , R 3 , R 5 and R 6 are independently selected from the group consisting of H, methyl, or ethyl; and n and m are independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
the process comprising a step wherein a compound or a mixture of compounds of general formula (II):

wherein R 1 , R 4 , m and n have the meaning as given above;
is reacted with a mixture of water and methanol in a weight/weight ratio of 90/10, 80/20, 70/30, 60/40, 50/50, 40/60, 30/70, 20/80 or 10/90; or a mixture of water, methanol, and ethanol in a weight/weight/weight ratio of 30/60/10, 20/60/20, 20/70/10 or 10/70/20 to obtain the compound or the mixture of compounds of general structure (I);

or
comprising a step wherein a compound or a mixture of compounds of general formula (III):

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , m and n have the meaning as given above;
is reacted with bromine, a bromide ion or a bromonium ion, to obtain the compound or a mixture of compounds of general structure (I); and obtaining the compound or the mixture of compounds of general structure (III) in a step wherein a compound or a mixture of compounds of general formula (VI):

wherein R 1 and R 4 are independently selected from the group consisting of H, methyl, Cl and Br; and n and m are independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
is reacted with a mixture of water and methanol in a weight/weight ratio of 90/10, 80/20, 70/30, 60/40, 50/50, 40/60, 30/70, 20/80 or 10/90; or a mixture of water, methanol and ethanol in a weight/weight/weight ratio of 30/60/10, 20/60/20, 20/70/10 or 10/70/20.

2. The process according to claim 1 comprising the step wherein the compound or the mixture of compounds of general formula (II):

wherein R 1 and R 4 are independently selected from the group consisting of H, methyl, Cl and Br; and n and m are independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10
is reacted with a mixture of water and methanol in a weight/weight ratio of 90/10, 80/20, 70/30, 60/40, 50/50, 40/60, 30/70, 20/80 or 10/90; or a mixture of water, methanol, and ethanol in a weight/weight/weight ratio of 30/60/10, 20/60/20, 20/70/10 or 10/70/20, to obtain the compound or the mixture of compounds of general structure (I);
and further comprising obtaining the compound or the mixture of compounds of general formula (II) in a step wherein a compound or a mixture of compounds of general formula (IV):

wherein R 1 and R 4 are independently selected from the group consisting of H, methyl and Cl; X 1 , X 2 , Y 2 are independently selected from OH, Cl and Br, with the proviso that at least one substituent selected from X 1 and Y 1 is OH and at least one substituent selected from X 2 and Y 2 is OH; and n and m are independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
is reacted with an acid or a base.

3. The process according to claim 2 further comprising obtaining the compound or the mixture of compounds of general formula (IV) in a step wherein a compound or a mixture of compounds of general formula (V):

wherein R 1 and R 4 are independently selected from the group consisting of H, methyl, Cl and Br; X 1 , X 2 , Y 1 , Y 2 are independently selected from OH, Cl and Br, with the proviso that at least one substituent selected from X 1 and Y 1 is OH and at least one substituent selected from X 2 and Y 2 is OH; and n and m are independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
is reacted with bromine, a bromide ion or a bromonium ion.

4. The process according to claim 3 further comprising obtaining the compound or the mixture of compounds of general formula (V) in a step wherein epichlorohydrin is reacted with but-2-yne-1,4-diol.

5. The process according to claim 4 wherein epichlorohydrin is reacted with but-2-yne-1,4-diol in presence of an acid or a base.

6. The process according to claim 5 wherein epichlorohydrin is reacted with but-2-yne-1,4-diol in presence of an acid.

7. The process of claim 3 , wherein the compound or the mixture of compounds of general formula (V) is reacted with bromine.

8. The process according to claim 1 further comprising obtaining the compound or the mixture of compounds of general formula (VI) in a step wherein a compound or a mixture of compounds of general formula (V):

wherein R 1 and R 4 are independently selected from the group consisting of H, methyl, Cl and Br; X 1 , X 2 , Y 1 , Y 2 are independently selected from OH, Cl and Br, with the proviso that at least one substituent selected from X 1 and Y 1 is OH and at least one substituent selected from X 2 and Y 2 is OH; and n and m are independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
is reacted with an acid or a base.

9. The process according to claim 8 further comprising obtaining the compound or the mixture of compounds of general formula (V) in a step wherein epichlorohydrin is reacted with but-2-yne-1,4-diol.

10. The process according to claim 9 wherein epichlorohydrin is reacted with but-2-yne-1,4-diol in presence of an acid or a base.

11. The process according to claim 10 wherein epichlorohydrin is reacted with but-2-yne-1,4-diol in presence of an acid.

12. The process according to claim 1 wherein R 1 and R 4 are Cl.

13. The process according to claim 1 wherein R 1 , R 3 , R 5 and R 6 are independently selected from H and methyl.

14. The process according to claim 1 wherein m is 0.

15. A mixture of compounds of general formula (I):

wherein R 1 and R 4 are independently selected from the group consisting of H, methyl, Cl, and Br; R 2 , R 3 , R 5 and R 6 are independently selected from the group consisting of H, methyl, or ethyl; and n and m are independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; produced by the process of claim 1 .

16. A process for the preparation of a flame-retardant blend, the process comprising a step of blending the product of the process according to claim 1 with a further flame-retardant.

17. A process for the preparation of a premix comprising a step of blending the product of the step or the steps according to claim 1 with a blowing agent and optionally one or more further components selected from the list consisting of further polyol compounds, foam stabilizer, further blowing agents, further flame retardants, catalysts, cross-linking agents and surfactants.

18. A process

Assignees

• Solvay

Inventors

• Collin Andre
• Walraevens Rene

Classifications

• C08G18/4018

  Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48 · CPC title

• C08J9/125

  Water, e.g. hydrated salts · CPC title

• C08G2101/00

  Manufacture of cellular products · CPC title

• C07C41/22

  by introduction of halogens; by substitution of halogen atoms by other halogen atoms · CPC title

• C07C43/1786

  containing halogen · CPC title