US5194167A
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Quaternary ammonium salts of mercaptothiadiazoles and related heterocyclic derivatives as antioxidant and antiwear additives
Assignee: Mobil Oil AS
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Filing: 1991-05-08
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Granted: 1993-03-16
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Expires: 2011-05-08
Abstract
Abstract Quaternary ammonium salts of mercaptothiadiazoles and related heterocyclic derivatives have been found to be 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 00:51
CPC Classifications
C; C07; C07D; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/12; C07D285/125; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/143; C10L1/24; C10L1/2443; C10L1/2456; C10L1/2462; C10L1/2475; C10L10/00; C10L10/04; C10L10/08; C10M; C10M135/00; C10M135/32; C10M135/36; C10L1/18; C10L1/182; C10L1/1828; C10L1/192; C10L1/195; C10L1/196; C10L1/1963; C10L1/2431; C10L1/2437; C10L1/2493; C10M2207/00; C10M2207/28; C10M2207/281; C10M2207/282; C10M2207/283; C10M2207/286; C10M2219/00; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
106 words
An improved lubricant composition comprising a major proportion of an oil of lubricating viscosity or grease prepared there from and a minor amount of from about 0.001 to about 10 wt % of a multifunctional antiwear, antioxidant additive product of reaction prepared by reacting a heterocyclic compound selected from the group consisting of mercaptothiadiazoles or dimercaptothiadiazole with a quaternary ammonium salt and a carboxylic acid anhydride in substantially molar, less than molar or more than molar amounts at temperatures varying from ambient to about 150° C. under pressures varying from ambient to slightly higher for a time sufficient to obtain the desired additive product of reaction.
Claim 2
Dependent Claim
106 words
An improved lubricant composition comprising a major proportion of an oil of lubricating viscosity or grease prepared there from and a minor amount of from about 0.001 to about 10 wt % of a multifunctional antiwear, antioxidant additive product of reaction prepared by reacting a heterocyclic compound selected from the group consisting of mercaptothiadiazoles or dimercaptothiadiazole with a quaternary ammonium salt and a carboxylic acid anhydride in substantially molar, less than molar or more than molar amounts at temperatures varying from ambient to about 150° C. under pressures varying from ambient to slightly higher for a time sufficient to obtain the desired additive product of reaction.
Claim 3
Dependent Claim
85 words
The composition of claim 1 wherein the product contains the following structural formula: ##STR2## and wherein R + is N+R 1 R 2 R 3 R 4 , a tetra-substituted ammonium ion in which the groups attached to the nitrogen may be the same or different and C 1 to about C 40 hydrocarbyl optionally containing sulfur, oxygen, nitrogen or mixtures thereof and R' is C 1 to about C 40 hydrocarbyl or polyhydrocarbyl selected from the group consisting of alkyl, aryl, alkaryl or aralkyl.
Claim 4
Dependent Claim
85 words
The composition of claim 1 wherein the product contains the following structural formula: ##STR3## and wherein R + is N+R 1 R 2 R 3 R 4 , a tetra-substituted ammonium ion in which the groups attached to the nitrogen may be the same or different and C 1 to about C 40 hydrocarbyl optionally containing sulfur, oxygen, nitrogen or mixtures thereof and R' is C 1 to about C 40 hydrocarbyl or polyhydrocarbyl selected from the group consisting of alkyl, aryl, alkaryl or aralkyl.
Claim 5
Dependent Claim
12 words
The composition of claim 1 wherein the heterocyclic compound is a dimercaptothiadiazole.
Claim 6
Dependent Claim
11 words
The composition of claim 4 wherein the heterocyclic compound is 2,5-dimercapto-1,3,4-thiadiazole.
Claim 7
Dependent Claim
15 words
The composition of claim 1 wherein the reactants are 2,5-dimercapto-1,3,4-thiadiazole, tricaprylmethylammonium chloride, and 2-dodecen-1-ylsuccinic anhydride.
Claim 8
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 9
Dependent Claim
30 words
The composition of claim 7 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 10
Dependent Claim
12 words
The composition of claim 7 wherein the lubricant is a synthetic oil.
Claim 11
Dependent Claim
12 words
The composition of claim 9 wherein the lubricant is an ester oil.
Claim 12
Dependent Claim
76 words
A process for preparing a multifunctional antioxidant, antiwear additive product by reacting a heterocyclic compound selected from the group consisting of mercaptothiadiazoles or dimercaptothiadiazoles with a quaternary ammonium salt and a hydrocarbyl carboxylic acid with anhydride in substantially molar, less than molar or more than molar ratios at temperatures varying from ambient to about 150° C. under pressures varying from ambient to slightly higher for a time sufficient to obtain the desired additive product of reaction.
Claim 13
Dependent Claim
76 words
A process for preparing a multifunctional antioxidant, antiwear additive product by reacting a heterocyclic compound selected from the group consisting of mercaptothiadiazoles or dimercaptothiadiazoles with a quaternary ammonium salt and a hydrocarbyl carboxylic acid with anhydride in substantially molar, less than molar or more than molar ratios at temperatures varying from ambient to about 150° C. under pressures varying from ambient to slightly higher for a time sufficient to obtain the desired additive product of reaction.
Claim 14
Dependent Claim
85 words
The process of claim 11 wherein the product contains the following structural formula: ##STR4## and R + is N+R 1 R 2 R 3 R 4 , a tetra-substituted ammonium ion in which the groups attached to the nitrogen may be the same or different and are C 1 to about C 40 hydrocarbyl optionally containing sulfur, oxygen, nitrogen or mixtures thereof and R' is C 1 to about C 40 hydrocarbyl or polyhydrocarbyl selected from the group consisting of alkyl, aryl, alkaryl or aralkyl.
Claim 15
Dependent Claim
86 words
The process of claim 11 wherein the product contains the following structural formula: ##STR5## and wherein R + is N+R 1 R 2 R 3 R 4 , a tetra-substituted ammonium ion in which the groups attached to the nitrogen may be the same or different and are C 1 to about C 40 hydrocarbyl optionally containing sulfur, oxygen, nitrogen or mixtures thereof and R' is C 1 to about C 40 hydrocarbyl or polyhydrocarbyl selected from the group consisting of alkyl, aryl, alkaryl or aralkyl.
Claim 16
Dependent Claim
12 words
The process of claim 11 wherein the heterocyclic compound is a dimercaptothiadiazole.
Claim 17
Dependent Claim
11 words
The process of claim 14 wherein the heterocyclic compound is 2,5-dimercapto-1,3,4-thiadiazole.
Claim 18
Dependent Claim
15 words
The process of claim 11 wherein the reactants are 2,5-dimercapto-1,3,4-thiadiazole, tricaprylmethylammonium chloride, and 2-dodecen-1-ylsuccinic anhydride.
Claim 19
Dependent Claim
79 words
A product of reaction suitable for use as an antioxidant and antiwear additive in lubricants prepared by reacting a heterocyclic compound selected from the group consisting of mercaptothiadiazoles or dimercaptothiadiazoles with a quaternary ammonium salt and carboxylic acid anhydride in substantially molar, less than molar or more than molar amounts at temperatures varying from ambient to about 150° C. under pressures varying from ambient to slightly higher for a time sufficient to obtain the desired additive product of reaction.
Claim 20
Dependent Claim
79 words
A product of reaction suitable for use as an antioxidant and antiwear additive in lubricants prepared by reacting a heterocyclic compound selected from the group consisting of mercaptothiadiazoles or dimercaptothiadiazoles with a quaternary ammonium salt and carboxylic acid anhydride in substantially molar, less than molar or more than molar amounts at temperatures varying from ambient to about 150° C. under pressures varying from ambient to slightly higher for a time sufficient to obtain the desired additive product of reaction.
Claim 21
Dependent Claim
86 words
The product of claim 17 wherein the product contains the following structural formula: ##STR6## and wherein R + is N+R 1 R 2 R 3 R 4 , a tetra-substituted ammonium ion in which the group attached to the nitrogen may be the same or different and is C 1 to about C 40 hydrocarbyl optionally containing sulfur, oxygen, nitrogen or mixtures thereof and R' is C 1 to about C 40 hydrocarbyl or polyhydrocarbyl selected from the group consisting of alkyl, aryl, alkaryl or aralkyl.
Claim 22
Dependent Claim
85 words
The product of claim 17 wherein the product contains the following structural formula: ##STR7## wherein R + is N+R 1 R 2 R 3 R 4 , a tetra-substituted ammonium ion in which the groups attached to the nitrogen may be the same or different and are C 1 to about C 40 hydrocarbyl optionally containing sulfur, oxygen, nitrogen or mixtures thereof and R' is C 1 to about C 40 hydrocarbyl or polyhydrocarbyl selected from the group consisting of alkyl, aryl, alkaryl or aralkyl.
Claim 23
Dependent Claim
12 words
The product of claim 17 wherein the heterocyclic compound is a dimercaptothiadiazole.
Claim 24
Dependent Claim
11 words
The product of claim 20 wherein the heterocyclic compound is 2,5-dimercapto-1,3,4-thiadiazole.
Claim 25
Dependent Claim
15 words
The product of claim 17 wherein the reactants are 2,5-dimercapto-1,3,4-thiadiazole, tricaprylmethylammonium chloride, and 2-dodecen-1-ylsuccinic anhydride.
Claim 26
Dependent Claim
30 words
A method of preparing an improved lubricant composition comprising adding to said lubricant a minor multifunctional antioxidant, antiwear amount of an additive product of reaction as described in claim 17.
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