US5132034A
Expired / Lapsed
US
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Thioester derived hindered phenols and aryl-amines as antioxidant and antiwear additives
Assignee: Mobil Oil AS
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Filing: 1991-05-08
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Granted: 1992-07-21
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Expires: 2011-05-08
Abstract
Abstract Thioester derived hindered phenols & thioester derived arylamines are effective antioxidant and antiwear additives for lubricants and fuels.
Inventors
- 👤 Shih-Ying Hsu
- 👤 Andrew G. Horodysky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 08:51
CPC Classifications
C; C10; C10M; C10M159/00; C10M159/12; C10M129/00; C10M129/02; C10M129/04; C10M129/10; C10M129/12; C10M129/68; C10M129/72; C10M129/86; C10M129/95; C10M133/00; C10M133/02; C10M133/04; C10M133/12; C10M135/00; C10M135/20; C10M135/22; C10M135/26; C10M2203/00; C10M2203/10; C10M2203/102; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/025; C10M2207/026; C10M2207/027; C10M2207/28; C10M2207/282; C10M2207/285; C10M2207/286; C10M2207/34; C10M2215/00; C10M2215/02; C10M2215/06; C10M2215/064; C10M2215/065; C10M2215/066; C10M2215/067; C10M2215/068; C10M2219/00; C10M2219/08; C10M2219/082; C10M2219/085; C10M2227/00
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
89 words
An improved lubricant composition comprising a major proportion of said lubricant and a minor proportion of a multifunctional antiwear, antioxidant additive product prepared by the reaction of: (A) one of either a hindered phenol or an arylamine, with (B) a hydrocarbyl succinic anhydride, and (C) a thioester, in equimolar ratios or slightly in excess of any one of the reactants at temperatures varying from ambient to about 200° C., under atmospheric pressure for a time sufficient to obtain a hydrocarbyl thioester derivative of an arylamine or a hindered phenol.
Claim 2
Dependent Claim
89 words
An improved lubricant composition comprising a major proportion of said lubricant and a minor proportion of a multifunctional antiwear, antioxidant additive product prepared by the reaction of: (A) one of either a hindered phenol or an arylamine, with (B) a hydrocarbyl succinic anhydride, and (C) a thioester, in equimolar ratios or slightly in excess of any one of the reactants at temperatures varying from ambient to about 200° C., under atmospheric pressure for a time sufficient to obtain a hydrocarbyl thioester derivative of an arylamine or a hindered phenol.
Claim 3
Dependent Claim
65 words
The composition of claim 1 wherein the additive product is prepared in the following manner: ##STR2## Where R=hydrogen, or C 1 -C 100 hydrocarbyl, polyhydrocarbyl optionally containing sulfur, nitrogen and/or oxygen; R' and R"=hydrogen or C 1 to about C 120 hydrocarbyl and optionally containing sulfur, nitrogen and/or oxygen and where hydrocarbyl is selected from the group consisting of alkyl, alkenyl, alkaryl, aralkyl or aryl.
Claim 4
Dependent Claim
74 words
The composition of claim 1 wherein the product containing at least one additive product of reaction having the following structural formula: ##STR3## and wherein R=hydrogen or C 1 to about C 120 hydrocarbyl, or polyhydrocarbyl and optionally containing sulfur, nitrogen and/or oxygen; R'=hydrogen or C 1 to about C 120 hydrocarbyl, and optionally containing sulfur, nitrogen and/or oxygen and where hydrocarbyl is selected from the group consisting of alkyl, alkenyl, alkaryl, aralkyl or aryl.
Claim 5
Dependent Claim
74 words
The composition of claim 1 wherein the product contains at least one additive product of reaction having the following structural formula: ##STR4## and where R=hydrogen or C 1 to about C 120 hydrocarbyl or a polyhydrocarbyl and optionally containing sulfur, nitrogen and/or oxygen; R'=hydrogen C 1 to about C 120 hydrocarbyl, and optionally containing sulfur, nitrogen and/or oxygen and where hydrocarbyl is selected from the group consisting of alkyl, alkenyl, alkaryl, aralkyl or aryl.
Claim 6
Dependent Claim
19 words
The composition of claim 1 wherein the thioester derived hinderedphenol is prepared from 2,6-t-butyl-4-hydroxymethylphenol, 2-dodecen-1-ylsuccinic anhydride and iso-decyl thioglycolate.
Claim 7
Dependent Claim
18 words
The composition of claim 1 wherein the thioester derived arylamine is prepared from di(octylphenyl)amine, 2-dodecen-1-ylsuccinic anhydride and iso-decylthioglycolate.
Claim 8
Dependent Claim
19 words
The composition of claim 1 wherein the thioester derived hinderedphenol is prepared from 2,6-t-butyl-4-hydroxymethylphenol, 2-dodecen-1-ylsuccinic anhydride and glycol dimercaptoacetate.
Claim 9
Dependent Claim
19 words
The composition of claim 1 wherein the thioester derived arylamine is prepared from di(octylphenyl)amine, 2-dodecenyl-1-ylsuccinic anhydride and glycol dimercaptoacetate.
Claim 10
Dependent Claim
48 words
The composition of claim 1 wherein the lubricant is an oil of lubricating viscosity selected from the group consisting of (1) mineral oils, (2) synthetic oils, (3) or mixtures of mineral and synthetic oils or is (4) a grease prepared from any one of (1), (2) or (3).
Claim 11
Dependent Claim
30 words
The composition of claim 9 wherein the lubricant contains from about 0.001 to about 10 wt% based on the total weight of the composition of the additive product of reaction.
Claim 12
Dependent Claim
12 words
The composition of claim 9 wherein the lubricant is a synthetic oil.
Claim 13
Dependent Claim
11 words
The composition of 9 wherein the lubricant is a mineral oil.
Claim 14
Dependent Claim
11 words
The composition of 9 wherein the lubricant is a mineral oil.
Claim 15
Dependent Claim
69 words
A hydrocarbyl thioester derivative of an arylamine or a hindered phenol prepared by the reaction of: (A) one of either a hindered phenol or an arylamine, with (B) a hydrocarbyl succinic anhydride, and (C) a thioester, in equimolar ratios or slightly in excess of any one of the reactants at temperatures varying from ambient to about 200° C., under atmospheric pressure for a time sufficient to obtain said derivatives.
Claim 16
Dependent Claim
69 words
A hydrocarbyl thioester derivative of an arylamine or a hindered phenol prepared by the reaction of: (A) one of either a hindered phenol or an arylamine, with (B) a hydrocarbyl succinic anhydride, and (C) a thioester, in equimolar ratios or slightly in excess of any one of the reactants at temperatures varying from ambient to about 200° C., under atmospheric pressure for a time sufficient to obtain said derivatives.
Claim 17
Dependent Claim
77 words
A product of reaction in which accordance with claim 13 wherein the product contains at least one product of reaction having the following structure: ##STR5## and where R=hydrogen or C 1 to about C 120 hydrocarbyl or a polyhydrocarbyl and optionally containing sulfur, nitrogen and/or oxygen; R'=hydrogen C 1 to about C 120 hydrocarbyl, and optionally containing sulfur, nitrogen and/or oxygen and where hydrocarbyl is selected from the group consisting of alkyl, alkenyl, alkaryl, aralkyl or aryl.
Claim 18
Dependent Claim
64 words
The product of claim 13 wherein the product contains the following structural formula: ##STR6## and wherein R=hydrogen or C 1 -C 120 hydrocarbyl or polyhydrocarbyl and optionally contains sulfur, nitrogen and/or oxygen; R' and R"=hydrogen or C 1 -C 120 hydrocarbyl and wherein hydrocarbyl is selected from the group consisting of alkyl, alkenyl, alkaryl, aralkyl, and aryl and optionally contains sulfur, nitrogen and/or oxygen.
Claim 19
Dependent Claim
19 words
The product of claim 13 wherein the thioester derived hinderedphenol is prepared from 2,6-t-butyl-4-hydroxymethylphenol, 2-dodecen-1-ylsuccinic anhydride and iso-decyl thioglycolate.
Claim 20
Dependent Claim
19 words
The product of claim 13 wherein the thioester derived arylamine is prepared from di(octylphenyl)amine, 2-dodecen-1 -ylsuccinic anhydride and iso-decylthioglycolate.
Claim 21
Dependent Claim
19 words
The product of claim 13 wherein the thioester derived hinderedphenol is prepared from 2,6-t-butyl-4-hydroxymethylphenol, 2-dodecen-1-ylsuccinic anhydride and glycol dimercaptoacetate.
Claim 22
Dependent Claim
20 words
The product of claim 13 wherein the thioester derived arylamine is prepared from di(octylphenyl)amine, 2-dodecen -1-ylsuccinic anhydride and glycol dimercaptoacetate.
Claim 23
Dependent Claim
30 words
A method of preparing an improved lubricant composition comprising adding to said lubricant a minor multifunctional antioxidant and/or antiwear amount of a product of reaction as described in claim 18.
Claim 24
Dependent Claim
38 words
The method of claim 20 wherein said composition is a lubricant composition and said minor amount is from about 0.001 to about 10 wt% based on the total weight of the composition of said additive product of reaction.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1995-07-21 | 1996-01-20 | 1996-07-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-07-21 | 2000-01-20 | 2000-07-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-07-21 | 2004-01-20 | 2004-07-21 | $7700.00 | Window Closed / Lapsed |