US3933907A
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Thiophosphorus acid amides
Assignee: Imperial Chemical Industries Ltd
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Filing: 1974-01-17
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Granted: 1976-01-20
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Expires: 1994-01-17
Abstract
Abstract Amides of phosphorus-containing thioacids are reacted with sulphenyl halides to give phosphorus-containing thioacid amides in which one or more of the nitrogen atoms carries a substituent attached through a sulphur atom. These substituted amides are inhibitors of premature vulcanisation in rubbers. The most effective compounds carry a secondary alkylthio or cycloalkylthio on each nitrogen atom.
Inventors
- 👤 Stanley Ashton
- 👤 Vijay Ratna Sharma
- 👤 John Anthony Taylor
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 22:07
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6564; C07F9/6581; C07F9/6584; C07F9/65848; C07F9/06; C07F9/22; C07F9/24; C07F9/2454; C07F9/2479; C07F9/28; C07F9/30; C07F9/36; C07F9/38; C07F9/44; C07F9/4461; C07F9/4484; C07F9/4488; C08; C08K; C08K5/00; C08K5/49; C08K5/51; C08K5/5399
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
151 words
An amide of the formula: ##EQU4## wherein R is alkyl of up to 18 carbon atoms, alkenyl of up to 18 carbon atoms, cycloalkyl containing 5-6 carbon atoms, phenyl, naphthyl, tolyl, β-methoxyethyl, β-cyanoethyl, 2-formylprop-2-yl, 4-chlorophenyl, 4-methoxyphenyl, 4-dimethylaminophenyl, 2-nitrophenyl, 4-nitrophenyl, 2,3,4,5,6-pentachlorophenyl, 2-methoxycarbonylphenyl or 4-phenylsulphonylphenyl, R 1 is hydrogen, alkyl of up to 18 carbon atoms, alkenyl of up to 18 carbon atoms, cycloalkyl containing 5-6 carbon atoms, phenyl, naphthyl, tolyl, β-methoxyethyl, β-cyanoethyl, 2-formylprop-2-yl, 4-chlorophenyl, 4-methoxyphenyl, 4-dimethylaminophenyl, 2-nitrophenyl, 4-nitrophenyl, 2,3,4,5,6-pentachlorophenyl, 2-methoxycarbonylphenyl or 4-phenylsulphonylphenyl or a group of the formula ##EQU5## wherein R 6 is hydrogen or one of the values of R given above, one of R 2 and R 3 is R -- S -- NR 1 -- and the other is R -- S -- NR 1 --, halogen, a value as recited for R or --OR wherein R and R 1 , in each instance, have the meaning given above.
Claim 2
Dependent Claim
151 words
An amide of the formula: ##EQU4## wherein R is alkyl of up to 18 carbon atoms, alkenyl of up to 18 carbon atoms, cycloalkyl containing 5-6 carbon atoms, phenyl, naphthyl, tolyl, β-methoxyethyl, β-cyanoethyl, 2-formylprop-2-yl, 4-chlorophenyl, 4-methoxyphenyl, 4-dimethylaminophenyl, 2-nitrophenyl, 4-nitrophenyl, 2,3,4,5,6-pentachlorophenyl, 2-methoxycarbonylphenyl or 4-phenylsulphonylphenyl, R 1 is hydrogen, alkyl of up to 18 carbon atoms, alkenyl of up to 18 carbon atoms, cycloalkyl containing 5-6 carbon atoms, phenyl, naphthyl, tolyl, β-methoxyethyl, β-cyanoethyl, 2-formylprop-2-yl, 4-chlorophenyl, 4-methoxyphenyl, 4-dimethylaminophenyl, 2-nitrophenyl, 4-nitrophenyl, 2,3,4,5,6-pentachlorophenyl, 2-methoxycarbonylphenyl or 4-phenylsulphonylphenyl or a group of the formula ##EQU5## wherein R 6 is hydrogen or one of the values of R given above, one of R 2 and R 3 is R -- S -- NR 1 -- and the other is R -- S -- NR 1 --, halogen, a value as recited for R or --OR wherein R and R 1 , in each instance, have the meaning given above.
Claim 3
Dependent Claim
21 words
An amide according to claim 1 wherein R is a secondary alkyl or cycloalkyl and R 1 is alkyl or cycloalkyl.
Claim 4
Dependent Claim
21 words
An amide according to claim 1 wherein both R 2 and R 3 are R -- S -- NR 1 --.
Claim 5
Dependent Claim
95 words
An amide according to claim 1 wherein R is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, hexyl, n-octyl, tert-octyl, n-dodecyl, tert-dodecyl, n-octadecyl, propenyl, n-but-1-enyl, isobutenyl, n-pent-1-enyl, dodecenyl, n-octadecenyl, cyclopentyl, cyclohexyl, phenyl, o-, m- and p-tolyl, naphthyl, β-methoxyethyl, β-cyanoethyl, 2-formylprop-2-yl, 4-chlorophenyl, 4-methoxyphenyl, 4-dimethylaminophenyl, 2-nitrophenyl, 4-nitrophenyl, 2,3,4,5,6-pentachlorophenyl, 2-methoxycarbonylphenyl or 4-phenylsulphonylphenyl; R 1 is hydrogen, one of the values recited for R, CH 3 --CH=N--, R 6 --CO-- or R 6 --SO 2 -- wherein R 6 is hydrogen, methyl, phenyl or tolyl and both R 2 and R 3 are R -- S -- NR 1 --.
Claim 6
Dependent Claim
60 words
An amide selected from the group consisting of N,n',n"-trimethyl-N,N',N"-tris(isopropylthio)phosphorothioic triamide, N,n',n"-tri-n-butyl-N,N' ,N"-tris(cyclohexylthio)phosphorothioic triamide, N,n',n"-tricyclohexyl-N,N',N"-tris(isopropylthio)phosphorothioic triamide N,n',n" -trimethyl-N,N' ,N"-tris(phenylthio)phosphorothioic triamide, N,n',n"-triethyl-N,N',N" -tris(n-butylthio)phosphorothioic triamide, N,n',n"-triphenyl-N,N',N"-tris(cyclohexylthio)phosphorothioic triamide, N,n',n" -trimethyl-N,N',N"-tris(t.-butylthio)phosphorothioic triamide, N,n',n" -tri-n-butyl-N,N',N"-tris(benzylthio)phosphorothioic triamide, N,n'-diethyl-N,N'-bis(isopropylthio)phosphorodiamidothioic chloride, 1,3-bis(phenylthio)-2-thiono-2-ethoxy-1,3,2-diazaphospholane, N,n'-diphenyl-N,N'-bis(4-methoxyphenylthio)phosphorodiamidothioic chloride O,n,n'-trimethyl-N,N'-bis(isopropylthio)phosphorodiamido thionate, O-methyl-N,N'-dicyclohexyl-N,N'-bis(2-chlorophenylthio)phosphorodiamido thionate, O-methyl-N,N'-di-n-butyl-N,N'-bis(chloromethylthio)phosphorodiamido thionate, O-phenyl-N,N'-dimethyl-N,N'-bis(methylthio)phosphorodiamido thionate, N,n',n" -tris(n-dodecylthio)-2-thiono-2-phenylamino-1,3,2-diazaphospholane. O,o'-dimethyl-N-cyclohexyl-N-isopropylthiophosphoroamido thionate, O,o'-diethyl-N-n-butyl-N-cyclohexylthiophosphoroamido thionate, O,o'-diethyl-N-benzyl-N-methylthiophosphoroamido thionate, N,n'-dimethyl-N,N'-bis(isopropylthio)phenylphosphonothioic diamide, N,n'-di-n-butyl-N,N'-bis(phenylthio)-p-tolylphosphorothioic diamide, P,p,n-drimethyl-N-t.-butylthiophosphinothioic amide and P,p,n-diphenyl-N-cyclohexyl-N-benzylthiophosphinothioic amide.
Claim 7
Dependent Claim
60 words
An amide selected from the group consisting of N,n',n"-trimethyl-N,N',N"-tris(isopropylthio)phosphorothioic triamide, N,n',n"-tri-n-butyl-N,N' ,N"-tris(cyclohexylthio)phosphorothioic triamide, N,n',n"-tricyclohexyl-N,N',N"-tris(isopropylthio)phosphorothioic triamide N,n',n" -trimethyl-N,N' ,N"-tris(phenylthio)phosphorothioic triamide, N,n',n"-triethyl-N,N',N" -tris(n-butylthio)phosphorothioic triamide, N,n',n"-triphenyl-N,N',N"-tris(cyclohexylthio)phosphorothioic triamide, N,n',n" -trimethyl-N,N',N"-tris(t.-butylthio)phosphorothioic triamide, N,n',n" -tri-n-butyl-N,N',N"-tris(benzylthio)phosphorothioic triamide, N,n'-diethyl-N,N'-bis(isopropylthio)phosphorodiamidothioic chloride, 1,3-bis(phenylthio)-2-thiono-2-ethoxy-1,3,2-diazaphospholane, N,n'-diphenyl-N,N'-bis(4-methoxyphenylthio)phosphorodiamidothioic chloride O,n,n'-trimethyl-N,N'-bis(isopropylthio)phosphorodiamido thionate, O-methyl-N,N'-dicyclohexyl-N,N'-bis(2-chlorophenylthio)phosphorodiamido thionate, O-methyl-N,N'-di-n-butyl-N,N'-bis(chloromethylthio)phosphorodiamido thionate, O-phenyl-N,N'-dimethyl-N,N'-bis(methylthio)phosphorodiamido thionate, N,n',n" -tris(n-dodecylthio)-2-thiono-2-phenylamino-1,3,2-diazaphospholane. O,o'-dimethyl-N-cyclohexyl-N-isopropylthiophosphoroamido thionate, O,o'-diethyl-N-n-butyl-N-cyclohexylthiophosphoroamido thionate, O,o'-diethyl-N-benzyl-N-methylthiophosphoroamido thionate, N,n'-dimethyl-N,N'-bis(isopropylthio)phenylphosphonothioic diamide, N,n'-di-n-butyl-N,N'-bis(phenylthio)-p-tolylphosphorothioic diamide, P,p,n-drimethyl-N-t.-butylthiophosphinothioic amide and P,p,n-diphenyl-N-cyclohexyl-N-benzylthiophosphinothioic amide.
Claim 8
Dependent Claim
15 words
The amide of claim 1 which is N, N', N" -tris (isopropylthio)-N,N',N"-tris cyclohexyl phosphorothioic triamide.
References Cited (Backward Citations)
DE1022587B
Cited
US3755507A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-19 | 1979-07-21 | 1980-01-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-19 | 1983-07-21 | 1984-01-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-19 | 1987-07-21 | 1988-01-20 | $7700.00 | Window Closed / Lapsed |