IP Library Granted Patent US 11,945,933
Granted Patent B2
US 11,945,933 · App. 17/503,960 · Granted Apr 2, 2024

Stabilized polyurethane composition

Inventors: Jonathan Hill (Reinach Blonay, CH); Maurice Power (Reinach Blonay, CH)
Assignee: SI Group, Inc.
C08K5/13C08G18/165C08G18/2063C08G18/244C08G18/48C08G18/7621C08J9/0023C08K5/1345C08K5/375C08G2110/0083C08J2375/04
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Quick Facts
Patent No.
US 11,945,933
App. No.
17/503,960
Granted
Apr 2, 2024
Kind
B2
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.

Claims (31)

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.

Assignments (8)
RELEASE OF SECURITY INTEREST Recorded Dec 30, 2025
From: ALTER DOMUS (US) LLC, AS COLLATERAL AGENT
To: SI GROUP, INC.
Reel/Frame 074136/0039 →
ASSIGNMENT OF SECURITY INTEREST IN PATENTS [REEL 068968/FRAME 0001] Recorded Dec 24, 2024
From: JPMORGAN CHASE BANK, N.A.
To: ALTER DOMUS (US) LLC
Reel/Frame 069770/0736 →
SECURITY INTEREST Recorded Sep 19, 2024
From: SI GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 068968/0001 →
SECURITY INTEREST Recorded Sep 19, 2024
From: SI GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 068968/0024 →
MERGER Recorded Feb 16, 2023
From: SI GROUP USA (USAA), LLC
To: SI GROUP, INC.
Reel/Frame 062719/0326 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 25, 2022
From: HILL, JONATHAN; POWER, MAURICE
To: ADDIVANT USA LLC
Reel/Frame 059510/0888 →
CHANGE OF NAME Recorded Mar 25, 2022
From: ADDIVANT USA, LLC
To: SI GROUP USA (USAA), LLC
Reel/Frame 059510/0895 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 25, 2022
From: ADDIVANT SWITZERLAND GMBH
To: ADDIVANT USA, LLC
Reel/Frame 059397/0981 →
Priority Claims (1)
GB 1515640 · Sep 3, 2015 · national
Continuity (2)
Division 15754916
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