IP Library Granted Patent US 12,168,726
Granted Patent B2
US 12,168,726 · App. 17/297,822 · Granted Dec 17, 2024

Antioxidant compositions

Inventors: Clément Barrière (Whitefield, GB); Maurice Power (Manchester, GB)
C08K5/46C08K5/1345C08K5/18C08K5/375C08K2201/014
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Quick Facts
Patent No.
US 12,168,726
App. No.
17/297,822
Granted
Dec 17, 2024
Kind
B2
Abstract

The invention provides a stabilising composition for polymeric materials, comprising: a. a first derivatised phenolic antioxidant; b. at least one secondary arylamine having the formula (I): NHRyRx wherein: the or each R, which may be the same or different, independently denotes an optionally substituted hydrocarbyl group; x and y are each independently from 0 to 5 provided that at least one of x and y is at least 1; and provided that at least one R is an optionally substituted hydrocarbyl group having at least 9 carbon atoms; and c. one or more antioxidant boosters independently selected from: i. a second derivatised phenolic antioxidant having lower steric hindrance than the first derivatised phenolic antioxidant; ii. a hindered amine; iii. an optionally substituted phenothiazine; and also the use of the stabilising composition for stabilising polyol and/or polyurethane; and a stabilised composition comprising a polyol and/or polyurethane and the aforementioned low emission and anti-scorch stabilising composition.

Claims (32)

1. A stabilising composition for polymeric materials, comprising:

a. a first derivatised phenolic antioxidant having a molecular weight of at least 390 present in an amount of from 20 to 60% w/w based on the total weight of the stabilising composition;

b. at least one secondary arylamine having the formula I:

wherein:

each R, which may be the same or different, independently denotes an optionally substituted hydrocarbyl group; x and y are each independently from 0 to 5 provided that at least one of x and y is at least 1; and provided that at least one R is an unsubstituted cycloalkyl, straight chain alkyl, or branched chain alkyl hydrocarbyl group having at least 9 carbon atoms, wherein the at least one secondary arylamine is present in an amount of from 35 to 75% w/w of the stabilising composition; and

c. one or more antioxidant boosters selected from the group consisting of:

i. a second derivatised phenolic antioxidant having lower steric hindrance than the first derivatised phenolic antioxidant wherein the second derivatized phenolic antioxidant comprises a bridged bisphenol, a di-hydroxybenzene, and/or a tri-hydroxybenzene wherein, the one or more antioxidant boosters is present in an amount of from 0.25 to 15 w/w of the stabilizing composition.

2. The stabilising composition according to claim 1 , wherein at least one of R x and R y is an optionally substituted hydrocarbyl group having 9 carbon atoms.

3. The stabilising composition according to claim 2 , wherein at least one of R x and R y is a nonyl group.

4. The stabilising composition according to claim 1 , wherein x and y are each independently from 0 to 2 provided that at least one of x and y is at least 1.

5. The stabilising composition according to claim 1 , wherein the stabilising composition is substantially free from diphenylamine and from lower alkylated diphenylamine antioxidants.

6. The stabilising composition according to claim 1 , wherein the stabilising composition is substantially free from t-butylated diphenylamines.

7. The stabilising composition according to claim 1 , wherein the first derivatised phenolic antioxidant has a molecular weight of at least about 400.

8. The stabilising composition according to claim 1 , wherein the second derivatised phenolic antioxidant has a molecular weight lower than about 600.

9. The stabilising composition according to claim 1 , wherein the second derivatised phenolic antioxidant has:

a. the number of substituent groups ortho to a phenolic hydroxyl group in the second derivatised phenolic antioxidant is lower than the number of substituent groups ortho to a phenolic hydroxyl group in the first derivatised phenolic antioxidant; and/or

b. the size of any substituent group ortho to a phenolic hydroxyl group in the second derivatised phenolic antioxidant is smaller than the size of any substituent group ortho to a phenolic hydroxyl group in the first derivatised phenolic antioxidant.

10. The stabilising composition according to claim 1 , wherein the second derivatized phenolic antioxidant is selected from the group consisting of, a di-hydroxybenzene, and a tri-hydroxybenzene.

11. The stabilising composition according to claim 1 , wherein the composition is a liquid at 25° C. and atmospheric pressure.

12. The stabilising composition according to claim 1 , wherein the stabilising composition is substantially free from secondary or tertiary arylamines having vapour pressures above 0.03 Pa at 20° C.

13. The stabilising composition according to claim 12 , wherein the secondary or tertiary arylamines having vapour pressures above 0.03 Pa at 20° C. are each present in an amount of less than 2.0% w/w of the stabilising composition.

14. The stabilising composition according to claim 13 , wherein the total amount of secondary or tertiary arylamines having vapour pressures above 0.03 Pa at 20° C. is less than 2.0% w/w of the stabilising composition.

15. The stabilising composition according to claim 1 , wherein the contribution to VOC of the stabilising composition is less than 20 ppm.

16. The stabilising composition according to claim 1 , wherein the contribution to condensable emissions of the stabilising composition is less than 200 ppm.

17. The stabilising composition according to claim 1 , wherein the first derivatised phenolic antioxidant comprises a phenol group which is substituted.

18. The stabilising composition according to claim 17 , wherein the substituted phenol comprises an alkyl substituent.

19. The stabilising composition according to claim 1 , wherein the first derivatised phenolic antioxidant is present in an amount of from 25 to 55% w/w.

20. The stabilising composition according to claim 1 , wherein the at least one secondary arylamine is present in an amount of from 40 to 70% w/w.

21. A stabilised composition comprising a polyol and a stabilising composition according to claim 1 .

22. A stabilised composition comprising a polyurethane and a stabilising composition according to claim 1 .

23. The stabilised composition according to claim 21 , wherein the stabilising composition is present in the stabilised composition in an amount of from about 0.01 to about 2% by weight of the polymeric material.

24. The stabilised composition according to claim 22 , wherein the stabilising composition is present in the stabilised composition in an amount of from about 0.01 to about 2% by weight of the polymeric material.

Assignments (6)
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 Jul 1, 2021
From: BARRIÈRE, CLÉMENT; POWER, MAURICE
To: SI GROUP USA (USAA), LLC
Reel/Frame 056732/0888 →