IP Library › Granted Patent US 12,486,467
Granted Patent B2
US 12,486,467 · App. 18/569,488 · Granted Dec 2, 2025

O-alkylated sterically hindered antioxidants

Inventors: Jun Dong (Friendswood, TX); Jeonkyu Lee (Ulsan, KR); Gerard Mulqueen (Frauenfeld, CH); Shinhyun Kim (Ulsan, KR)
Assignee: SONGWON INDUSTRIAL CO., LTD.
C10M129/70C07C69/734C08K5/1345C10M129/76C10M169/04C10M2207/282C10M2207/284C10N2030/02C10N2030/10C10N2030/20C10N2040/25
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Quick Facts
Patent No.
US 12,486,467
App. No.
18/569,488
Granted
Dec 2, 2025
Kind
B2
Abstract

The present invention relates to a composition a composition comprising compound of the general formula (I) in which R 1 a straight or branched C1-C24 alkyl group; R 2 is a C1-C8 alkyl group; R 3 is a C1-C8 alkyl group. The invention also relates to industrial products such as additive blends, engine oils and polymer compositions comprising this compound of the general formula (I) and to the use the compound of the general formula (I) as an additive such in industrial products such as additive blends, engine oils and polymer compositions.

Claims (45)

1 . A composition comprising

i) a compound of the general formula (I)

in which

R 1 is a C7-C9 alkyl group;

R 2 is a methyl group; and

R 3 is a tert-butyl group.

2 . The composition according to claim 1 , wherein

R1 is an isooctyl group or a 2-ethylhexyl group.

3 . The composition according to claim 1 , wherein the composition comprises at least 0.1 wt.-% of the compound of the general formula (I), based on the total weight of the composition.

4 . The composition according to claim 3 , wherein the composition comprises at least 50 wt.-% of the compound of the general formula (I), based on the total weight of the composition.

5 . The composition according to claim 4 , wherein the composition comprises at least 90 wt.-% of the compound of the general formula (I), based on the total weight of the composition.

6 . The composition according to claim 2 , further comprising

ii) isooctyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate.

7 . The composition according to claim 6 , wherein the composition comprises

i) at least 0.01 wt.-% isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate;

ii) at least 25 wt.-% isooctyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate;

in each case based on the total weight of components i) and ii) in the composition.

8 . The composition according to claim 7 , wherein the composition comprises

iii) less than 5 wt.-% of compounds selected from the group consisting of diisooctyl- α-(3,5-di-tert-butyl-4-hydroxybenzyl) glutarate, di-tert-butylphenol, methyl-3,5-di- tert-butyl-4-hydroxyhydrocinnamate and isooctanol, based on the total weight of components i), ii) and iii) in the composition.

9 . The composition according to claim 8 , wherein the composition comprises isooctyl-3,5-di-tert-butyl-4-methoxy-hydrocinnamate and diisooctyl-α- (3,5-di-tert-butyl-4-hydroxybenzyl) glutarate in a weight ratio of at least 2:1.

10 . The composition according to claim 6 , wherein the composition comprises 1 to 50 wt.-% of the compound of the general formula (I), based on the total weight of the composition.

11 . The composition according to claim 10 , wherein the composition comprises 2.5 to 35 wt.-% of the compound of the general formula (I), based on the total weight of the composition.

12 . The composition according to claim 6 , wherein at least one of the following conditions (α1) to (α5) is fulfilled:

(α1) the composition has a kinematic viscosity (determined at a temperature of 40° C. according to ASTM D 445) in the range from 60 to 300 cSt;

(α2) the composition has a Gardner colour (determined according to ASTM D 1544) of less than 10 Gardner;

(α3) the composition has water content (determined according to ASTM E 203) of less than 0.5 wt.-%;

(α4) the composition has a specific gravity (determined at a temperature of 25° C. according to ASTM D 1298) in the range from 0.900 to 1.020;

(α5) the composition has a total acid number (as determined by the ASTM D664) of less than 5.0 mg KOH/g.

13 . The composition according to claim 1 , wherein the total amount of component i) in the composition is at least 95 wt.-%, based on the total weight of the composition.

14 . The composition according to claim 1 , wherein the composition is an additive blend, wherein the total amount of component i) in the composition is in the range from 0.01 to 50 wt.-%, based on the total weight of the additive blend.

15 . The composition according to claim 1 , wherein the composition is an engine oil further comprising at least one base oil.

16 . The composition according to claim 15 , wherein the total amount of component i) in the composition is in the range from 0.01 to 5 wt.-%, based on the total weight of the engine oil.

17 . The composition according to claim 1 , wherein the composition is a polymer composition further comprising a polymer.

18 . The composition according to claim 17 , wherein the total amount of component i) in the composition is in the range from 0.01 to 5 wt.-%, based on the total weight of the polymer composition.

19 . The composition according to claim 1 , wherein the composition is an additive present in additive blends, engine oils or polymer compositions.

20 . A compound of the general formula (I)

in which

R 1 is a straight or branched C7-C9 alkyl group;

R 2 is a methyl group;

R 3 is a tert-butyl group,

wherein the compound is an additive present in additive blends, engine oils or polymer compositions.

21 . The composition according to claim 6 , wherein the total amount of components i) and ii) in the composition is at least 95 wt.-%, based on the total weight of the composition.

22 . The composition according to claim 6 , wherein the composition is an additive blend and wherein the total amount of components i) and ii) in the composition is in the range from 0.01 to 50 wt.-%, based on the total weight of the additive blend.

23 . The composition according to claim 6 , wherein the composition is an engine oil comprising at least one base oil and wherein the total amount of components i) and ii) in the composition is in the range from 0.01 to 5 wt.-%, based on the total weight of the engine oil.

24 . The composition according to claim 6 , wherein the composition is a polymer composition comprising a polymer and wherein the total amount of components i) and ii) in the composition is in the range from 0.01 to 5 wt.-%, based on the total weight of the polymer composition.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 12, 2023
From: DONG, JUN; LEE, JEONKYU; MULQUEEN, GERARD; KIM, SHINHYUN
To: SONGWON INDUSTRIAL CO., LTD.
Reel/Frame 065967/0289 →
Continuity (2)
Provisional Application 63214888 · Jun 25, 2021
Related Publication 20240279565A1 · Aug 22, 2024
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