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US3932403A Expired / Lapsed US ⏱️ 0.0 years remaining

Phosphorus acid amides

Assignee: Imperial Chemical Industries Ltd
•
Filing: 1973-07-20
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Granted: 1976-01-13
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Expires: 1993-07-20
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Abstract

Abstract Amides of phosphorus-containing acids are reacted with sulphenyl halides to give phosphorus-containing acid amides in which one or more of the nitrogen atoms carries the appropriate substitutent attached through a sulphur atom. These substituted amides are inhibitors of premature vulcanisation in rubbers. The most effective compounds are arylamides substituted by secondary alkylthio groups.

Inventors

  • 👤 Stanley Ashton
  • 👤 Vijay Ratna Sharma
  • 👤 John Anthony Taylor

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 16:18
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/44; C07F9/4461; C07F9/4484; C07F9/4488; C07F9/06; C07F9/22; C07F9/224; C07F9/228; C07F9/24; C07F9/2454; C07F9/2479; C07F9/30; C07F9/36; C08; C08K; C08K5/00; C08K5/49; C08K5/5399

Claims Analysis

Total Claims: 5
Claim 1
Independent Claim 155 words
An amide of the formula ##EQU3## wherein R is alkyl of up to 18 carbon atoms, 2-formylprop-2-yl, alkenyl of up to 18 carbon atoms, cyclopentyl, cyclohexyl, phenyl, tolyl, butyl phenyl, naphthyl, β-methyoxyethyl, β-cyanoethyl, 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, 2-formylprop2-yl, alkenyl of up to 18 carbon atoms, cyclopentyl, cyclohexyl, phenyl, tolyl, naphthyl, β-methoxyethyl, β-cyanoethyl, 4-chlorophenyl, 4-methoxyphenyl, 4-dimethylaminophenyl, 2-nitrophenyl, 4-nitrophenyl, 2,3,4,5,6-pentachlorophenyl, 2-methoxycarbonylphenyl, 4-phenylsulphonylphenyl, p-toluene sulphonyl, acetyl or N=CH-R where R has the meaning stated above; R 2 and R 3 are each a group R-S-NR 1 where each of R and R 1 have the meaning stated above, hydrogen, halogen, a value as recited for R, 2-benzothiazolylthio, 2-benzoxazolythio, 2-benzimidazolylthio, 2-pyrimidinylthio or 2-triazinylthio groups, amino, ethylamino, diethylamino, dimethylamino, phenylamino, methylphenylamino or ethylphenylamino; or R 2 and R 3 together with the phosphorus atom joining them form 2-oxo-1,3,2-diazaphospholane, 2-oxo-4,5-benzo-1,3,2-diazaphospholane, 2-oxo-1,3,2-oxazaphospholane, 2-oxo-4,5-benzo-1,3,2-oxazaphospholane, 2-oxo-4,5-benzo-1,3-thiazaphospholane, or 2-oxo-2,3-dithiaphospholane.
Claim 2
Dependent Claim 155 words
An amide of the formula ##EQU3## wherein R is alkyl of up to 18 carbon atoms, 2-formylprop-2-yl, alkenyl of up to 18 carbon atoms, cyclopentyl, cyclohexyl, phenyl, tolyl, butyl phenyl, naphthyl, β-methyoxyethyl, β-cyanoethyl, 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, 2-formylprop2-yl, alkenyl of up to 18 carbon atoms, cyclopentyl, cyclohexyl, phenyl, tolyl, naphthyl, β-methoxyethyl, β-cyanoethyl, 4-chlorophenyl, 4-methoxyphenyl, 4-dimethylaminophenyl, 2-nitrophenyl, 4-nitrophenyl, 2,3,4,5,6-pentachlorophenyl, 2-methoxycarbonylphenyl, 4-phenylsulphonylphenyl, p-toluene sulphonyl, acetyl or N=CH-R where R has the meaning stated above; R 2 and R 3 are each a group R-S-NR 1 where each of R and R 1 have the meaning stated above, hydrogen, halogen, a value as recited for R, 2-benzothiazolylthio, 2-benzoxazolythio, 2-benzimidazolylthio, 2-pyrimidinylthio or 2-triazinylthio groups, amino, ethylamino, diethylamino, dimethylamino, phenylamino, methylphenylamino or ethylphenylamino; or R 2 and R 3 together with the phosphorus atom joining them form 2-oxo-1,3,2-diazaphospholane, 2-oxo-4,5-benzo-1,3,2-diazaphospholane, 2-oxo-1,3,2-oxazaphospholane, 2-oxo-4,5-benzo-1,3,2-oxazaphospholane, 2-oxo-4,5-benzo-1,3-thiazaphospholane, or 2-oxo-2,3-dithiaphospholane.
Claim 3
Dependent Claim 16 words
An amide as claimed in claim 1 wherein R is a secondary alkyl, cyclopentyl or cyclohexyl.
Claim 4
Dependent Claim 12 words
An amide as claimed in claim 1 wherein R 1 is phenyl.
Claim 5
Dependent Claim 23 words
An amide as claimed in claim 1 wherein one or both of R 2 and R 3 is a group R-S-NR 1 .

References Cited (Backward Citations)

US3647856A Cited
US3737438A Cited
US3755507A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-01-12 1979-07-14 1980-01-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-01-12 1983-07-14 1984-01-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-01-12 1987-07-14 1988-01-13 $7700.00 Window Closed / Lapsed

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