Stabilized polyurethane composition

Patent metadata

Field	Value
Publication number	US-11945933-B2
Application number	US-202117503960-A
Country	US
Kind code	B2
Filing date	Oct 18, 2021
Priority date	Sep 3, 2015
Publication date	Apr 2, 2024
Grant date	Apr 2, 2024

Abstract

The present invention provides a stabilising composition, comprising:
a) a first phenolic antioxidant comprising one or more phenolic compounds having the structure of formula (I):

 wherein R 1 is a linear or branched alkyl group having from 12 to 20 carbon atoms; and
b) one or more second phenolic antioxidants independently selected from:
 a mono-hydroxybenzene having lower steric hindrance than the first phenolic antioxidant;
 a di-hydroxybenzene; and/or
 a tri-hydroxybenzene.

First claim

We claim:

1. A stabilized composition, comprising:
a) a polyurethane, or a polyurethane and a polyol; and
b) a stabilizing composition comprising:
i. a first phenolic antioxidant comprising two or more phenolic compounds having the structure of formula (I):

wherein R 1 is a linear or branched alkyl group having from 12 to 20 carbon atoms; and

ii) one or more second phenolic antioxidants independently selected from the group consisting of:
a mono-hydroxybenzene selected from the group consisting of α-tocopherol; 4,4′-thiobis(2-t-butyl-5-methylphenol), 2,2′-thiobis(6-t-butyl-4-methylphenol), 2,2′-methylenebis(6-t-butyl-4-methylphenol), 4,4′-butylidenebis[2-t-butyl-5-methylphenol], 2,2′-methylenebis(6-nonyl-p-cresol) and phenol, 4-methyl-, reaction products with dicyclopentadiene and isobutylene;
a di-hydroxybenzene selected from the group consisting of 4-tert-butylcatechol, 2,5-di-tert-amyl-hydroquinone, benzene-1,2-diol, benzene-1,3-diol, and benzene-1,4-diol, and
a tri-hydroxybenzene selected from the group consisting of benzene-1,2,3-triol, propyl 3,4,5-trihydroxybenzoate; and benzene-1,2,4-triol,

wherein the stabilizing composition does not contain a benzofuranone-based booster component.

2. The stabilized composition of claim 1 , wherein the stabilizing composition does not contain an amine-containing antioxidant.

3. The stabilized composition of claim 1 , wherein the polyol is present with the polyurethane and comprises a polyether polyol and/or a polyester polyol.

4. The stabilized composition of claim 1 , wherein the polyurethane comprises a polyurethane foam.

5. The stabilized composition of claim 1 , wherein the amount of stabilizing composition is present from about 0.01 to about 10%, by weight of the polyurethane or by weight of the polyurethane and the polyol.

6. The stabilized composition of claim 5 , wherein the amount of stabilizing composition is present from about 0.01 to about 5%, by weight of the polyurethane or by weight of the polyurethane and the polyol.

7. The stabilized composition of claim 5 , wherein the amount of stabilizing composition is present from about 0.01 to about 2%, by weight of the polyurethane or by weight of the polyurethane and the polyol.

8. The stabilized composition of claim 1 , wherein R1 is a linear or branched alkyl group having from 12 to 15 carbon atoms.

9. The stabilized composition of claim 1 , wherein R1 is a linear or branched alkyl group having from 13 to 15 carbon atoms.

10. The stabilized composition of claim 8 , wherein R1 is selected from the group consisting of a linear alkyl group having 12 carbon atoms, a branched alkyl group having 12 carbon atoms, a linear alkyl group having 13 carbon atoms, a branched alkyl group having 13 carbon atoms, a linear alkyl group having 14 carbon atoms, a branched alkyl group having 14 carbon atoms, a linear alkyl group having 15 carbon atoms, and a branched alkyl group having 15 carbon atoms.

11. The stabilized composition of claim 8 , wherein R1 is selected from the group consisting of a linear alkyl group having 13 carbon atoms, a branched alkyl group having 13 carbon atoms, a linear alkyl group having 14 carbon atoms, a branched alkyl group having 14 carbon atoms, a linear alkyl group having 15 carbon atoms, and a branched alkyl group having 15 carbon atoms.

12. The stabilized composition of claim 1 , wherein the first phenolic antioxidant comprises C13-C15 linear and branched alkyl esters of 3-(3′5′-di-t-butyl-4′-hydroxyphenyl) propionic acid.

13. The stabilized composition of claim 1 , wherein the first phenolic antioxidant is a liquid at ambient conditions.

14. The stabilized composition of claim 1 , wherein the one or more second phenolic antioxidants are selected from the group consisting of:
a di-hydroxybenzene selected from the group consisting of 4-tert-butylcatechol, 2,5-di-tert-amyl-hydroquinone, benzene-1,2-diol, and benzene-1,3-diol,
a tri-hydroxybenzene selected from the group consisting of benzene-1,2,3-triol; propyl 3,4,5-trihydroxybenzoate; and benzene-1,2,4-triol; and
a dimer or oligomer of mono-hydroxybenzene monomers selected from the group consisting of 4,4′-butylidenebis[2-t-butyl-5-methylphenol], and phenol, 4-methyl-, reaction products with dicyclopentadiene and isobutylene.

15. The stabilized composition of claim 1 , wherein the one or more second phenolic antioxidants are present in the stabilizing composition in an amount of from about 1 to about 50 wt. % based on the total weight of the stabilizing composition.

16. The stabilized composition of claim 15 , wherein the one or more second phenolic antioxidants are present in the stabilizing composition in an amount of from about 1 to about 35 wt. %, based on the total weight of the stabilizing composition.

17. The stabilized composition of claim 15 , wherein the one or more second phenolic antioxidants are present in the stabilizing composition in an amount of from about 5 to about 30 wt. %, based on the total weight of the stabilizing composition.

18. The stabilized composition of claim 15 , wherein the one or more second phenolic antioxidants are present in the stabilizing composition in an amount of from about 10 to about 25 wt. %, based on the total weight of the stabilizing composition.

19. The stabilized composition of claim 1 , wherein the stabilizing composition is a liquid at ambient conditions.

Assignees

• Si Group Usa Usaa Llc
• Si Group Inc

Inventors

• Hill Jonathan
• Power Maurice

Classifications

• C08K5/13 Primary

  Phenols; Phenolates · CPC title

• C08G18/165

  covered by C08G18/18 and C08G18/24 · CPC title

• C08G18/2063

  having two nitrogen atoms in the condensed ring system · CPC title

• C08G18/244

  tin salts of carboxylic acids · CPC title

• C08G18/48

  Polyethers · CPC title