US3892741A
Expired / Lapsed
US
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Preparation of thiocarbamylsulfenamides
Assignee: Goodrich Corp
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Filing: 1972-05-18
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Granted: 1975-07-01
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Expires: 1992-05-18
Abstract
Abstract Thiocarbamylsulfenamides are prepared in high yields in a process comprising the reaction of a monohaloamine with tri- or tetrathiocarbonate salt. The compounds have particular utility as accelerators in the vulcanization of unsaturated polymers.
Inventors
- 👤 Ray D Taylor
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 08:33
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/36; C08K5/43
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
44 words
A PROCESS FOR THE PREPARATION OF THICARBAMYSULFENAMIDES COMPRISING THE REACTION OF, AS THE ONLY REACTANTS, (1) A MONOHALOAMINE(S) OF THE FORMULA X-A WHEREIN X IS SELECTED FROM THE GROUP CONSISTING OF -C1, -BR, AND -I, AND A IS SELECTED FROM THE GROUP CONSISTING OF
Claim 2
Dependent Claim
44 words
A PROCESS FOR THE PREPARATION OF THICARBAMYSULFENAMIDES COMPRISING THE REACTION OF, AS THE ONLY REACTANTS, (1) A MONOHALOAMINE(S) OF THE FORMULA X-A WHEREIN X IS SELECTED FROM THE GROUP CONSISTING OF -C1, -BR, AND -I, AND A IS SELECTED FROM THE GROUP CONSISTING OF
Claim 3
Dependent Claim
18 words
A process of claim 1 wherein the monohaloamine is slurried in a water solution of the thiocarbonate salt.
Claim 4
Dependent Claim
28 words
A process of claim 2 wherein the monohaloamine is dissolved in a chlorinated organic solvent selected from the group consisting of carbon tetrachloride, chloroform, ethylene dichloride, and 1,1,2-trichloroethane.
Claim 5
Dependent Claim
9 words
A process of claim 3 wherein when A is
Claim 6
Dependent Claim
42 words
A process of claim 4 wherein the monohaloamine is dissolved in an organic solvent selected from the group consisting of carbon tetrachloride, chloroform, dichloroethylene, and 1,1,2-trichloroethane and this non-aqueous solution is admixed with an aqueous solution of said thiocarbonate salt in water.
Claim 7
Dependent Claim
18 words
A process of claim 5 where in the thiocarbonate salt, M is an alkali metal and z 2.
Claim 8
Dependent Claim
22 words
A process of claim 6 wherein -X of said monohaloamine is -Cl, and the thiocarbonate salt is sodium trithiocarbonate or sodium tetrathiocarbonate.
Claim 9
Dependent Claim
29 words
A process of claim 7 wherein the monochloroamine is selected from the group consisting of dimethylchloroamine, oxydiethyleneamine chloride, tetramethyleneamine chloride, pentamethyleneamine chloride, hexamethyleneamine chloride, and 3, 5-dimethyl oxydiethyleneamine chloride.
Claim 10
Dependent Claim
27 words
A process of claim 1 wherein the monohaloamine is used at the level of essentially two moles of monohaloamine to every one mole of thiocarbonate salt present.
Claim 11
Dependent Claim
33 words
A process of claim 1 wherein the monohaloamine is prepared in situ, prior to the reaction between the monohaloamine and the thiocarbonate salt, by reacting a primary or secondary amine with sodium hypochlorite.
Claim 12
Dependent Claim
61 words
A process for the preparation of a thiocarbamylsulfenamide comprising the reaction of, as the only reactants, (1) 0.2 mole of oxydiethyleneamine chloride and (2) 0.1 mole of sodium trithiocarbonate, at a temperature of from 0*C. to 28*C., wherein the said oxydiethyleneamine chloride is employed as a solution in chloroform and the said sodium trithiocarbonate is employed as a solution in water.
Claim 13
Dependent Claim
61 words
A process for the preparation of a thiocarbamylsulfenamide comprising the reaction of, as the only reactants, (1) 0.2 mole of oxydiethyleneamine chloride and (2) 0.1 mole of sodium trithiocarbonate, at a temperature of from 0*C. to 28*C., wherein the said oxydiethyleneamine chloride is employed as a solution in chloroform and the said sodium trithiocarbonate is employed as a solution in water.
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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) | 1978-06-30 | 1978-12-30 | 1979-07-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-06-30 | 1982-12-30 | 1983-07-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-06-30 | 1986-12-30 | 1987-07-01 | $7700.00 | Window Closed / Lapsed |