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US 3,933,907 AGranted
Thiophosphorus acid amides
AssigneeImperial Chemical Industries PLC
InventorsStanley Ashton, Vijay Ratna Sharma, John Anthony Taylor
Life of this patent
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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.
Claims6
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, .beta.-methoxyethyl, .beta.-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.sup.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, .beta.-methoxyethyl, .beta.-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.sup.6 is hydrogen or one of the values of R given above, one of R.sup.2 and R.sup.3 is R -- S -- NR.sup.1 -- and the other is R -- S -- NR.sup.1 --, halogen, a value as recited for R or --OR wherein R and R.sup.1, in each instance, have the meaning given above.
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.
20 more elements
Dependencies are inferred from the claim text.