US4097387A
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Olefin-dimercapto-thiadiazole compositions and process
Assignee: Ethyl Corp
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Filing: 1976-09-03
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Granted: 1978-06-27
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Expires: 1996-09-03
Abstract
Abstract Disclosed are a composition of matter, a process for making said composition, and a lubricating oil composition having improved anti-wear properties containing an effective amount of said composition of matter. The composition of matter comprises olefin-dimercapto-thiadiazole compositions, especially an oil soluble reaction product of an olefin; lithium, sodium or potassium 2,5-dimercapto-1,3,4-thiadiazole or mixtures thereof; and a member selected from the group consisting of S 2 Cl 2 , SCl 2 , S 2 Br 2 , SBr 2 , R-S-Cl, R-S-Br, and mixtures thereof, wherein R comprises C 1 -C 100 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl. Some of these compositions can be represented as follows: ##STR1## wherein X comprises R 1 -SS-R 2 , wherein R 1 comprises a C 6 -C 100 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl, and R 2 comprises R 1 or ##STR2## and wherein Y comprises H or X. Preferably R 1 comprises C 6 -C 100 alkene or alkane, still more perferably, C 6 -C 20 alkene or alkane. These compositions are effective wear inhibitors in lubricating oil. The process for making oil soluble derivatives of 2,5-dimercapto-1,3,4-thiadiazole comprises first reacting an olefin with a member selected from the group consisting of S 2 Cl 2 , SCl 2 , S 2 Br 2 , SBr 2 , R-S-Cl, R-S-Br, and mixtures thereof, to form a first reaction product; and then reacting said first reaction product with lithium, sodium or potassium 2,5-dimercapto-1,3,4-thiadiazole or mixtures thereof.
Inventors
- 👤 Gunter Caspari
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 02:17
CPC Classifications
C; C07; C07D; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/12; C07D285/125; C10; C10M; C10M135/00; C10M135/32; C10M135/36; C10M2207/00; C10M2207/28; C10M2207/282; C10M2207/34; C10M2207/40; C10M2207/404; C10M2219/00; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106
Claims Analysis
Total Claims: 53
Claim 1
Independent Claim
133 words
A lubricating oil composition having anti-wear properties comprising a major proportion of lubricating oil and an effective amount of an oil soluble additive, said additive comprising the oil soluble reaction product of an olefin; lithium, sodium or potassium 2,5-dimercapto-1,3,4-thiadiazole or mixtures thereof; and a sulfur compound selected from the group consisting of S 2 Cl 2 , SCl 2 , S 2 Br 2 , SBr 2 , R--S--Cl, R--S--Br, and mixtures thereof, wherein R comprises C 1 -C 100 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl and said additive comprises, ##STR5## wherein X comprises R 1 -- SS -- R 2 ; R 1 comprises C 6 -C 100 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl, and R 2 comprises R 1 or ##STR6## and Y comprises H or X.
Claim 2
Dependent Claim
133 words
A lubricating oil composition having anti-wear properties comprising a major proportion of lubricating oil and an effective amount of an oil soluble additive, said additive comprising the oil soluble reaction product of an olefin; lithium, sodium or potassium 2,5-dimercapto-1,3,4-thiadiazole or mixtures thereof; and a sulfur compound selected from the group consisting of S 2 Cl 2 , SCl 2 , S 2 Br 2 , SBr 2 , R--S--Cl, R--S--Br, and mixtures thereof, wherein R comprises C 1 -C 100 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl and said additive comprises, ##STR5## wherein X comprises R 1 -- SS -- R 2 ; R 1 comprises C 6 -C 100 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl, and R 2 comprises R 1 or ##STR6## and Y comprises H or X.
Claim 3
Dependent Claim
19 words
The composition of claim 1 wherein the olefin has a molecular weight of from about 80 to about 10,000.
Claim 4
Dependent Claim
19 words
The composition of claim 2 wherein the olefin has a moleuclar weight of from about 80 to about 500.
Claim 5
Dependent Claim
10 words
The composition of claim 1 wherein the olefin comprises alfa-olefins.
Claim 6
Dependent Claim
14 words
The composition of claim 4 wherein the alfa-olefins comprise C 6 -C 20 alfa-olefins.
Claim 7
Dependent Claim
20 words
The composition of claim 1 wherein R comprises C 1 -C 20 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl.
Claim 8
Dependent Claim
19 words
the composition of claim 1 wherein the molar ratio of sulfur compound to thiadiazole to olefin is about 0.1-10:0.1-10:1.
Claim 9
Dependent Claim
19 words
The composition of claim 7 wherein the molar ratio of sulfur compound to thiadiazole to olefin is about 0.3-1:2-4:1.
Claim 10
Dependent Claim
19 words
The composition of claim 8 wherein the molar ratio of sulfur compound to thiadiazole to olefin is about 0.4-0.6:2-4:1.
Claim 11
Dependent Claim
10 words
The composition of claim 5 wherein the alfa-olefins comprise isobutylene.
Claim 12
Dependent Claim
10 words
The composition of claim 5 wherein the alfa-olefins comprise 1-hexene.
Claim 13
Dependent Claim
10 words
The composition of claim 5 wherein the alfa-olefins comprise 1-octene.
Claim 14
Dependent Claim
17 words
The composition of claim 5 wherein the alfa-olefins comprise a mixture of C 11 -C 14 alfa-olefins.
Claim 15
Dependent Claim
17 words
The composition of claim 5 wherein the alfa-olefins comprise a mixture of C 15 -C 20 alfa-olefins.
Claim 16
Dependent Claim
30 words
The composition of claim 1 wherein the lubricating oil has a viscosity from about 40 Saybolt Universal Seconds at 100° F to about 200 Saybolt Universal Seconds at 210° F.
Claim 17
Dependent Claim
26 words
The composition of claim 1 wherein the additive is an oil soluble reaction product of an olefin, mono sodium 2,5-dimercapto-1,3,4-thiadiazole, and S 2 Cl 2 .
Claim 18
Dependent Claim
18 words
The composition of claim 1 wherein said additive is present at about 0.05 to about 5 weight percent.
Claim 19
Dependent Claim
18 words
The composition of claim 17 wherein said additive is present at about 0.1 to about 2 weight percent.
Claim 20
Dependent Claim
109 words
A composition comprising an oil soluble reaction product of an olefin; lithium; sodium or potassium 2,5-dimercapto-1,3,4-thiadiazole or mixtures thereof; and a member selected from the group consisting of S 2 Cl 2 , SCl 2 , S 2 Br 2 , SBr 2 , R--S--Cl, R--S--Br, and mixtures thereof, wherein R comprises C 1 -C 100 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl and said additive comprises, ##STR7## wherein X comprises R 1 -- SS -- R 2 ; R 1 comprises C 6 -C 100 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl, and R 2 comprises R 1 or ##STR8## and Y comprises H or X.
Claim 21
Dependent Claim
109 words
A composition comprising an oil soluble reaction product of an olefin; lithium; sodium or potassium 2,5-dimercapto-1,3,4-thiadiazole or mixtures thereof; and a member selected from the group consisting of S 2 Cl 2 , SCl 2 , S 2 Br 2 , SBr 2 , R--S--Cl, R--S--Br, and mixtures thereof, wherein R comprises C 1 -C 100 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl and said additive comprises, ##STR7## wherein X comprises R 1 -- SS -- R 2 ; R 1 comprises C 6 -C 100 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl, and R 2 comprises R 1 or ##STR8## and Y comprises H or X.
Claim 22
Dependent Claim
13 words
The composition of claim 19 comprising a reaction product of an olefin, 2,5-dimercapto-1,3,4-thiadiazole.
Claim 23
Dependent Claim
19 words
The composition of claim 19 wherein the olefin has a molecular weight of from about 80 to about 10,000.
Claim 24
Dependent Claim
19 words
The composition of claim 21 wherein the olefin has a molecular weight of from about 80 to about 500.
Claim 25
Dependent Claim
10 words
The composition of claim 19 wherein the olefin comprises alfa-olefins.
Claim 26
Dependent Claim
14 words
The composition of claim 23 wherein the alfa-olefins comprise C 6 -C 20 alfa-olefins.
Claim 27
Dependent Claim
20 words
The composition of claim 19 wherein R comprises C 1 -C 20 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl.
Claim 28
Dependent Claim
10 words
The composition of claim 24 wherein the alfa-olefins comprise isobutylene.
Claim 29
Dependent Claim
10 words
The composition of claim 24 wherein the alfa-olefins comprise 1-hexene.
Claim 30
Dependent Claim
19 words
The composition of claim 19 wherein the molar ratio of sulfur compound to thiadiazole to olefin is about 0.1-10:0.1-10:1.
Claim 31
Dependent Claim
19 words
The composition of claim 26 wherein the molar ratio of sulfur compound to thiadiazole to olefin is about 0.3-1:2-4:1.
Claim 32
Dependent Claim
19 words
The composition of claim 27 wherein the molar ratio of sulfur compound to thiadiazole to olefin is about 0.4-0.6:2-4:1.
Claim 33
Dependent Claim
10 words
The composition of claim 24 wherein the alfa-olefins comprise 1-octene.
Claim 34
Dependent Claim
17 words
The composition of claim 24 wherein the alfa-olefins comprise a mixture of C 11 -C 14 alfa-olefins.
Claim 35
Dependent Claim
17 words
The composition of claim 24 wherein the alfa-olefins comprise a mixture of C 15 -C 20 alfa-olefins.
Claim 36
Dependent Claim
82 words
A process for making oil soluble derivatives of 2,5-dimercapto-1,3,4-thiadiazole comprising first reacting an olefin with a sulfur compound selected from the group consisting of S 2 Cl 2 , SCl 2 , S 2 Br 2 , SBr 2 , R--S--Cl, R--S--Br, and mixtures thereof, to form a first reaction product; and then reacting said first reaction product with lithium, sodium or potassium 2,5-dimercapto-1,3,4-thiadiazole or mixtures thereof, wherein R comprises C 1 -C 100 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl.
Claim 37
Dependent Claim
82 words
A process for making oil soluble derivatives of 2,5-dimercapto-1,3,4-thiadiazole comprising first reacting an olefin with a sulfur compound selected from the group consisting of S 2 Cl 2 , SCl 2 , S 2 Br 2 , SBr 2 , R--S--Cl, R--S--Br, and mixtures thereof, to form a first reaction product; and then reacting said first reaction product with lithium, sodium or potassium 2,5-dimercapto-1,3,4-thiadiazole or mixtures thereof, wherein R comprises C 1 -C 100 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl.
Claim 38
Dependent Claim
13 words
The process of claim 34 wherein the reaction is conducted in a solvent.
Claim 39
Dependent Claim
19 words
The process of claim 34 wherein the molar ratio of sulfur compound to thiadiazole to olefin is about 0.1-10:0.1-10:1.
Claim 40
Dependent Claim
19 words
The process of claim 36 wherein the molar ratio of sulfur compound to thiadiazole to olefin is about 0.3-1:2-4:1.
Claim 41
Dependent Claim
19 words
The process of claim 37 wherein the molar ratio of sulfur compound to thiadiazole to olefin is about 0.4-0.6:2-4:1.
Claim 42
Dependent Claim
45 words
The process of claim 34 wherein the olefin and sulfur compound are reacted at a temperature from about 0° C. to about 200° C. and the first reaction product is reacted with the thiadiazole at a temperature from about 50° C. to about 200° C.
Claim 43
Dependent Claim
41 words
The process of claim 39 wherein the olefin and sulfur compound are reacted at a temperature from about 20° C. to about 60° C. and the first reaction product is reacted with the thiadiazole at a temperature of about 100° C.
Claim 44
Dependent Claim
20 words
The process of claim 34 wherein R comprises C 1 -C 20 hydrocarbyl or bromo, chloro or hydroxy substituted hydrocarbyl.
Claim 45
Dependent Claim
19 words
The process of claim 34 wherein the olefin has a molecular weight of from about 80 to about 10,000.
Claim 46
Dependent Claim
19 words
The process of claim 42 wherein the olefin has a molecular weight of from about 80 to about 500.
Claim 47
Dependent Claim
10 words
The process of claim 43 wherein the olefin comprises alfa-olefins.
Claim 48
Dependent Claim
14 words
The process of claim 44 wherein the alfa-olefins comprise C 6 -C 20 alfa-olefins.
Claim 49
Dependent Claim
10 words
The process of claim 44 wherein the alfa-olefins comprise isobutylene.
Claim 50
Dependent Claim
10 words
The process of claim 44 wherein the alfa-olefins comprise 1-hexene.
Claim 51
Dependent Claim
10 words
The process of claim 44 wherein the alfa-olefins comprise 1-octene.
Claim 52
Dependent Claim
17 words
The process of claim 44 wherein the alfa-olefins comprise a mixture of C 11 -C 14 alfa-olefins.
Claim 53
Dependent Claim
17 words
The process of claim 44 wherein the alfa-olefins comprise a mixture of C 15 -C 20 alfa-olefins.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-26 | 1981-12-26 | 1982-06-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-26 | 1985-12-26 | 1986-06-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-26 | 1989-12-26 | 1990-06-27 | $7700.00 | Window Closed / Lapsed |