US3914241A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Oil soluble derivatives of 2,5-di-mercapto-1,3,4-thiadiazole and process for preparation thereof
Assignee: Edwin Cooper and Co Ltd
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Filing: 1973-04-16
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Granted: 1975-10-21
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Expires: 1993-04-16
Abstract
Abstract A compound, suitable for use as a lubricant additive, is an oilsoluble reaction product of a di-(organo) dithiophosphoric acid, wherein the organo groups are aliphatic moieties, and a 1,3,4thiadiazole of the general formula: wherein X is a hydrogen atom or the residue of an ethylenically unsaturated alcohol, carboxylic acid, anhydride, amide, or imide, the reaction of the di-(organo) dithiophosphoric acid and the 1,3,4-thiadiazole being carried out in the presence of an oxidising agent. Also described are lubricating compositions containing the foregoing compounds as antioxidants and corrosion inhibitors.
Inventors
- 👤 John Scotchford Elliott
- 👤 Gerald John Joseph Jayne
- 👤 Rodney Ian Barber
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 12:27
CPC Classifications
C; C10; C10M; C10M137/00; C10M137/02; C10M137/04; C10M137/10; C10M137/105; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6536; C07F9/6539; C07F9/65392; C07F9/65395; C10M2203/00; C10M2203/10; C10M2203/102; C10M2207/00; C10M2207/28; C10M2207/282; C10M2207/287; C10M2207/289; C10M2207/34; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/24; C10M2215/26; C10M2217/00; C10M2217/04; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/02; C10M2219/022; C10M2219/08; C10M2219/082; C10M2219/083; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/045; C10M2223/047; C10N; C10N2010/00; C10N2010/04; C10N2030/00; C10N2030/12; C10N2070/00; C10N2070/02
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
117 words
A COMPOUND, SUITABLE FOR USE AS A LUBRICANT ADDITIVE, WHICH COMPOUND IS AN OIL SOLUBLE REACTION PRODUCT OF A DI-(ORGANO) DITHIOPHOSPHORIC ACID, WHEREIN THE ORGANO GROUPS ARE ALKYL OR ALKENYL OF 3 TO 18 C ATOMS, OPTIONALLY CONTAINING AN ALKOXY SUBSTITUENT, AND A 1,3,4-THIADIAZOLE SELECTED FROM THE GROUP CONSISTING OF 2,5-DIMERCAPTO-1,3,4-THIADIAZOLE AND A COMPOUND RESULTING FROM THE CONDENSATION REACTION OF 2,5DIMERCAPTO-1,3,4-THIADIAZOLE AT A TEMPERATURE IN THE RANGE OF ABOUT 120*-160*C WITH A COMPOUND SELECTED FROM THE GROUP CONSISTNG OF ALKENOLS AND ALKENOIC ACIDS OF 4 TO 18 CARBON ATOMS ND THE ANHYDRIDES, AMIDES AND IMIDES THEREOF, THE REACTION OF THE DI-(ORGANO) DI-THIOPHOSPHORIC ACID AND THE 1,3,4-THIADIAZOLE BEING CARRIED OUT IN THE PRESENCE OF A PEROXIDE OXIDIZING AGENT.
Claim 2
Dependent Claim
117 words
A COMPOUND, SUITABLE FOR USE AS A LUBRICANT ADDITIVE, WHICH COMPOUND IS AN OIL SOLUBLE REACTION PRODUCT OF A DI-(ORGANO) DITHIOPHOSPHORIC ACID, WHEREIN THE ORGANO GROUPS ARE ALKYL OR ALKENYL OF 3 TO 18 C ATOMS, OPTIONALLY CONTAINING AN ALKOXY SUBSTITUENT, AND A 1,3,4-THIADIAZOLE SELECTED FROM THE GROUP CONSISTING OF 2,5-DIMERCAPTO-1,3,4-THIADIAZOLE AND A COMPOUND RESULTING FROM THE CONDENSATION REACTION OF 2,5DIMERCAPTO-1,3,4-THIADIAZOLE AT A TEMPERATURE IN THE RANGE OF ABOUT 120*-160*C WITH A COMPOUND SELECTED FROM THE GROUP CONSISTNG OF ALKENOLS AND ALKENOIC ACIDS OF 4 TO 18 CARBON ATOMS ND THE ANHYDRIDES, AMIDES AND IMIDES THEREOF, THE REACTION OF THE DI-(ORGANO) DI-THIOPHOSPHORIC ACID AND THE 1,3,4-THIADIAZOLE BEING CARRIED OUT IN THE PRESENCE OF A PEROXIDE OXIDIZING AGENT.
Claim 3
Dependent Claim
50 words
A compound according to claim 1 wherein the organo groups are alkyl of 3 to 18 C atoms or alkyl and wherein the ethylenically unsaturated compound with which the 2,5-dimercapto-1,3,4-thiadiazole may be reacted is selected from the group consisting of alkenyl alcohols, alkenyl carboxylic acids and alkenyl carboxylic acid anhydrides.
Claim 4
Dependent Claim
30 words
A compound according to claim 1 wherein the organo groups are alkyl of 3 to 18 C atoms or allyl and wherein the di-(organo) dithiophosphoric acid is reacted with 2,5-di-mercapto-1,3,4-thiadiazole.
Claim 5
Dependent Claim
54 words
A compound according to claim 1 wherein the organo groups are alkyl of 3 to 18 C atoms or allyl and wherein the di-(organo) dithiophosphoric acid is reacted with a condensation reaction product of 2,5-dimercapto-1,3,4-thiadiazole with a compound selected from the group consisting of oleic acid, crotonic acid, oleyl alcohol and dodecenyl succinic anhydride.
Claim 6
Dependent Claim
35 words
A compound according to claim 1 wherein the organo groups of the di-(organo) dithiophosphoric acid are the same or different and at least one is an alkyl group containing from 3 to 10 carbon atoms.
Claim 7
Dependent Claim
18 words
A compound according to claim 1 wherein at least one of the organo groups bears an alkoxy substituent.
Claim 8
Dependent Claim
33 words
A compound according to claim 1 wherein the di-(organo)dithiophosphoric acid and the 1,3,4-thiadiazole are reacted in substantially the stoichiometric proportions required to substitute the desired number of dithiophosphate groups on the 1,3,4-thiadiazole nucleus.
Claim 9
Dependent Claim
20 words
A compound according to claim 1 wherein the reaction is carried out at a temperature of not more than 50*C.
Claim 10
Dependent Claim
13 words
A compound according to claim 1 wherein the oxidising agent is hydroGen peroxide.
Claim 11
Dependent Claim
20 words
A compound according to claim 1 wherein the reaction is carried out in an inert solvent such as petroleum ether.
Claim 12
Dependent Claim
131 words
A PROCESS FOR PREPARING A COMPOUND SUITABLE FOR USE AS A LUBRICANT ADDITIVE WHICH PROCESS COMPRISES REACTING AT A TEMPERATURE OF NOT MORE THAN 70*C A DI-(ORGANO) DITHIOPHOSPHORIC ACID, WHEREN THE ORGANO GROUPS ARE ALKYL OR ALKENYL OF 3 TO 18 C ATOMS, OPTIONALLY CONTAINING AN ALKOXY SUBSTITUENT, AND A 1,3,4-THIADIAZOLE SELECTED FROM THE GROUP CONSISTING OF 2,5-DIMERCAPTO-1,3,4-THIADIAZOLE AND A COMPOUND RESULTING FROM THE CONDENSATION REACTION OF 2,5-DIMERCAPTO 1,3,4THIADIAZOLE AT A TEMPERATURE IN THE RANGE OF ABOUT 120*-160*C WITH A COMPOUND SELECTED FROM THE GROUP CONSISTING OF ALKENOLS AND ALKENOIC ACIDS OF 4 TO 18 CARBON ATOMS AND THE ANHYDRIDES, AMIDES AND IMIDES THEREOF, THE REACTION OF THE DI-(ORGANO) DITHIOPHOSPHORIC ACID AND THE 1,3,4-THIADIAZOLE BEING CARRIED OUT IN THE PRESENCE OF A PERIOXIDE OXIDIZING AGENT TO FORM AN OIL-SOLUBLE REACTION PRODUCT.
Claim 13
Dependent Claim
131 words
A PROCESS FOR PREPARING A COMPOUND SUITABLE FOR USE AS A LUBRICANT ADDITIVE WHICH PROCESS COMPRISES REACTING AT A TEMPERATURE OF NOT MORE THAN 70*C A DI-(ORGANO) DITHIOPHOSPHORIC ACID, WHEREN THE ORGANO GROUPS ARE ALKYL OR ALKENYL OF 3 TO 18 C ATOMS, OPTIONALLY CONTAINING AN ALKOXY SUBSTITUENT, AND A 1,3,4-THIADIAZOLE SELECTED FROM THE GROUP CONSISTING OF 2,5-DIMERCAPTO-1,3,4-THIADIAZOLE AND A COMPOUND RESULTING FROM THE CONDENSATION REACTION OF 2,5-DIMERCAPTO 1,3,4THIADIAZOLE AT A TEMPERATURE IN THE RANGE OF ABOUT 120*-160*C WITH A COMPOUND SELECTED FROM THE GROUP CONSISTING OF ALKENOLS AND ALKENOIC ACIDS OF 4 TO 18 CARBON ATOMS AND THE ANHYDRIDES, AMIDES AND IMIDES THEREOF, THE REACTION OF THE DI-(ORGANO) DITHIOPHOSPHORIC ACID AND THE 1,3,4-THIADIAZOLE BEING CARRIED OUT IN THE PRESENCE OF A PERIOXIDE OXIDIZING AGENT TO FORM AN OIL-SOLUBLE REACTION PRODUCT.
References Cited (Backward Citations)
US3269896A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-10-20 | 1979-04-21 | 1979-10-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-10-20 | 1983-04-21 | 1983-10-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-10-20 | 1987-04-21 | 1987-10-21 | $7700.00 | Window Closed / Lapsed |