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US4432847A
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Poly sulfoxides from 1,3,4-thiadiazole-2,5-dithiol
Assignee: BP Corp North America Inc
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Filing: 1976-07-29
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Granted: 1984-02-21
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Expires: 1996-07-29
Abstract
Abstract Poly sulfoxides of the general formula ##STR1## where each R is a monovalent aliphatic radical bound to a sulfoxy group. Each R is defined as being individually selected from the group consisting of ##STR2## wherein R', R" and R"' are individually selected from the group consisting of alkyl moieties containing 1 to 22 carbon atoms, and aralkyl moieties, alkylated aryl moieties, heterocyclic alkyl moieties, cycloalkyl moieties containing 4 to 40 carbon atoms wherein the said moieties are joined to the sulfoxy group through the alkyl chain, the said moieties being unsubstituted and substituted, said substitutions being individually selected from the group consisting of halogen moieties, nitro moieties, alkoxy moieties, alkyl moieties, and dialkylamino moieties.
Inventors
- 👤 Ellis K. Fields
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 09:51
CPC Classifications
C; C07; C07D; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/12; C07D285/125; C07D417/00; C07D417/14; C10; C10M; C10M135/00; C10M135/32; C10M135/36; C10M2201/00; C10M2201/02; C10M2219/00; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106; C10N; C10N2040/00; C10N2040/20
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
27 words
A poly sulfoxide selected from the group consisting of: 2,5-bis(1-t-octylthiomethylsulfoxy)-1,3,4-thiadiazole; 2-(1-t-octylthiomethylsulfoxy)-5-(1-t-octylsulfoxymethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-t-octylsulfoxymethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-t-dodecylthiomethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-t-dodecylsulfoxymethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-t-hexadecylthiomethylsulfoxy)-1,3,4-thiadiazole; 2-(1-t-hexadecylthiomethylsulfoxy)-5-(1-t-hexadecylsulfoxymethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-t-hexadecylsulfoxymethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-t-hexadecylthio-1-hexylmethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-t-hexadecylsulfoxy-1-hexylmethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-octylthiomethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-octylsulfoxymethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(β-hydroxy-β-phenylethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(β-hydroxyoctyl-4-sulfoxy)-1,3,4-thiadiazole; 2,5-bis(β-hydroxydodecylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(β-hydroxy-β,4-pyridylethylsulfoxy)-1,3,4-thiadiazole and 2,5-bis(β-hydroxy-β,2-pyridylethylsulfoxy)-1,3,4-thiadiazole
Claim 2
Dependent Claim
27 words
A poly sulfoxide selected from the group consisting of: 2,5-bis(1-t-octylthiomethylsulfoxy)-1,3,4-thiadiazole; 2-(1-t-octylthiomethylsulfoxy)-5-(1-t-octylsulfoxymethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-t-octylsulfoxymethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-t-dodecylthiomethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-t-dodecylsulfoxymethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-t-hexadecylthiomethylsulfoxy)-1,3,4-thiadiazole; 2-(1-t-hexadecylthiomethylsulfoxy)-5-(1-t-hexadecylsulfoxymethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-t-hexadecylsulfoxymethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-t-hexadecylthio-1-hexylmethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-t-hexadecylsulfoxy-1-hexylmethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-octylthiomethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(1-octylsulfoxymethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(β-hydroxy-β-phenylethylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(β-hydroxyoctyl-4-sulfoxy)-1,3,4-thiadiazole; 2,5-bis(β-hydroxydodecylsulfoxy)-1,3,4-thiadiazole; 2,5-bis(β-hydroxy-β,4-pyridylethylsulfoxy)-1,3,4-thiadiazole and 2,5-bis(β-hydroxy-β,2-pyridylethylsulfoxy)-1,3,4-thiadiazole
Claim 3
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(1-t-octylthiomethylsulfoxy)-1,3,4-thiadiazole.
Claim 4
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2-(1-t-octylthiomethylsulfoxy)-5-(1-t-octylsulfoxymethylsulfoxy)-1,3,4-thiadiazole.
Claim 5
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(1-t-octylsulfoxymethylsulfoxy)-1,3,4-thiadiazole.
Claim 6
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(1-t-dodecylthiomethylsulfoxy)-1,3,4-thiadiazole.
Claim 7
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(1-t-dodecylsulfoxymethylsulfoxy)-1,3,4-thiadiazole.
Claim 8
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(1-t-hexadecylthiomethylsulfoxy)-1,3,4-thiadiazole.
Claim 9
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2-(1-t-hexadecylthiomethylsulfoxy)-5-(1-t-hexadecylsulfoxymethylsulfoxy)-1,3,4-thiadiazole.
Claim 10
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(1-t-hexadecylsulfoxymethylsulfoxy)-1,3,4-thiadiazole.
Claim 11
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(1-t-hexadecylthio-1-hexylmethylsulfoxy)-1,3,4-thiadiazole.
Claim 12
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(1-t-hexadecylsulfoxy-1-hexylmethylsulfoxy)-1,3,4-thiadiazole.
Claim 13
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(1-octylthiomethylsulfoxy)-1,3,4-thiadiazole.
Claim 14
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(1-octylsulfoxymethylsulfoxy)-1,3,4-thiadiazole.
Claim 15
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(β-hydroxy-β-phenylethylsulfoxy)-1,3,4-thiadiazole.
Claim 16
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(β-hydroxyoctyl-4-sulfoxy)-1,3,4-thiadiazole.
Claim 17
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(β-hydroxydodecylsulfoxy)-1,3,4-thiadiazole.
Claim 18
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(β-hydroxy-β,4-pyridylethylsulfoxy)-1,3,4-thiadiazole.
Claim 19
Dependent Claim
9 words
The poly sulfoxide of claim 1 which comprises 2,5-bis(β-hydroxy-β,2-pyridylethylsulfoxy)-1,3,4-thiadiazole.
Claim 20
Dependent Claim
123 words
A process for preparing polysulfoxides which comprises the selective oxidation of the reaction product of 1,3,4-thiadiazole-2,5-dithiol (DMTD) and an olefinically unsaturated compound wherein the said olefinically unsaturated compound is selected from the group of olefinically unsaturated compounds consisting of styrene, α-methylstyrene, α-p-dimethylstyrene, allylbenzene, cyclohexene, 1-vinylcyclohexene, ethylene, propylene, 1-butene, 1-octene, 1-dodecene, 1-octadecene, 2-vinylpyridine, 4-vinylpyridine, 2-vinylthiophene, 4-chlorostyrene, 4-nitrostyrene, eugenol methyl ether and 4-dimethylaminostyrene, wherein said DMTD is in the mole ratio to the olefinically unsaturated compound of 2:1 to 5:1 at a temperature within the range from about 0° C. to 40° C. with oxygen at 5-200 psig for 0.5 to 150 hours, and actinic radiation in the presence of a dye sensitizer selected from the group consisting of methylene blue, Eosine, and Rose Bengal.
Claim 21
Dependent Claim
123 words
A process for preparing polysulfoxides which comprises the selective oxidation of the reaction product of 1,3,4-thiadiazole-2,5-dithiol (DMTD) and an olefinically unsaturated compound wherein the said olefinically unsaturated compound is selected from the group of olefinically unsaturated compounds consisting of styrene, α-methylstyrene, α-p-dimethylstyrene, allylbenzene, cyclohexene, 1-vinylcyclohexene, ethylene, propylene, 1-butene, 1-octene, 1-dodecene, 1-octadecene, 2-vinylpyridine, 4-vinylpyridine, 2-vinylthiophene, 4-chlorostyrene, 4-nitrostyrene, eugenol methyl ether and 4-dimethylaminostyrene, wherein said DMTD is in the mole ratio to the olefinically unsaturated compound of 2:1 to 5:1 at a temperature within the range from about 0° C. to 40° C. with oxygen at 5-200 psig for 0.5 to 150 hours, and actinic radiation in the presence of a dye sensitizer selected from the group consisting of methylene blue, Eosine, and Rose Bengal.
References Cited (Backward Citations)
FR1568552A
Cited
US3753999A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-02-20 | 1987-08-22 | 1988-02-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-02-20 | 1991-08-22 | 1992-02-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-02-20 | 1995-08-22 | 1996-02-21 | $7700.00 | Window Closed / Lapsed |