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US4226738A
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N,N-Bis(trifluoromethylsulfonyl)oxamides and chemiluminescent compositions containing the same
Assignee: Omniglow Corp
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Filing: 1978-11-01
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Granted: 1980-10-07
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Expires: 1998-11-01
Abstract
Abstract N,N'-bis(trifluoromethylsulfonyl)oxamides are described with a number of variations by substitution at the amido nitrogen atoms. These compounds when used in chemiluminescent formulations will furnish superior light intensity and quantum efficiency. Preparation of compounds and their use for chemiluminescence are described.
Inventors
- 👤 Michael M. Rauhut
- 👤 Shin-Shyong Tseng
- 👤 Arthur G. Mohan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 17:14
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/76; C09; C09K; C09K11/00; C09K11/06; C09K11/07
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
238 words
A compound represented by formula (I) ##STR2## wherein R and R' independently represent hydrogen; alkyl of 1 to 6 carbon atoms; cycloalkyl of 4 to 8 carbon atoms; substituted alkyl or cycloalkyl wherein the substituents are selected from halo, carboxy, alkoxy, or alkoxycarbonyl, wherein the alkoxy is of 1 to 6 carbon atoms; alkanoyl of 2 to 18 carbon atoms; aroyl of 7 to 11 carbon atoms; aralkyl of 7 to 11 carbon atoms; aryl of 6 to 10 carbon atoms; heterocyclic aryl of 3 to 9 carbon atoms; substituted aryl and heterocyclic aryl of 6 to 10 and 3 to 9 carbon atoms, respectively, wherein the substituents, one or more, are selected from halo, nitro, cyano, trifluoromethyl, alkyl and alkoxy of 1 to 6 carbon atoms, hydroxy, phenoxy, benzyloxy, phenyl, alkanoylamino of 2 to 6 carbon atoms, benzoylamino, alkylsulfonyl of 1 to 6 carbon atoms, carboxy, alkoxycarbonyl and alkoxysulfonyl wherein the alkoxy group has 1 to 6 carbon atoms, --SO 3 .sup.⊖ M.sup.⊕ wherein M.sup.⊕ is a cation selected from sodium, potassium, lithium, ammonium, monoalkylammonium, dialkylammonium, trialkylammonium, or tetraalkylammonium wherein the alkyl radicals have 1 to 6 carbon atoms, and may be the same or different, aminocarbonyl, and aminosulfonyl which are unsubstituted or substituted at the nitrogen by 1 or 2 radicals selected from alkyl of 1 to 6 carbon atoms, phenyl, or substituted phenyl wherein the substituents are as defined above for aryl and heterocyclic aryl.
Claim 2
Dependent Claim
238 words
A compound represented by formula (I) ##STR2## wherein R and R' independently represent hydrogen; alkyl of 1 to 6 carbon atoms; cycloalkyl of 4 to 8 carbon atoms; substituted alkyl or cycloalkyl wherein the substituents are selected from halo, carboxy, alkoxy, or alkoxycarbonyl, wherein the alkoxy is of 1 to 6 carbon atoms; alkanoyl of 2 to 18 carbon atoms; aroyl of 7 to 11 carbon atoms; aralkyl of 7 to 11 carbon atoms; aryl of 6 to 10 carbon atoms; heterocyclic aryl of 3 to 9 carbon atoms; substituted aryl and heterocyclic aryl of 6 to 10 and 3 to 9 carbon atoms, respectively, wherein the substituents, one or more, are selected from halo, nitro, cyano, trifluoromethyl, alkyl and alkoxy of 1 to 6 carbon atoms, hydroxy, phenoxy, benzyloxy, phenyl, alkanoylamino of 2 to 6 carbon atoms, benzoylamino, alkylsulfonyl of 1 to 6 carbon atoms, carboxy, alkoxycarbonyl and alkoxysulfonyl wherein the alkoxy group has 1 to 6 carbon atoms, --SO 3 .sup.⊖ M.sup.⊕ wherein M.sup.⊕ is a cation selected from sodium, potassium, lithium, ammonium, monoalkylammonium, dialkylammonium, trialkylammonium, or tetraalkylammonium wherein the alkyl radicals have 1 to 6 carbon atoms, and may be the same or different, aminocarbonyl, and aminosulfonyl which are unsubstituted or substituted at the nitrogen by 1 or 2 radicals selected from alkyl of 1 to 6 carbon atoms, phenyl, or substituted phenyl wherein the substituents are as defined above for aryl and heterocyclic aryl.
Claim 3
Dependent Claim
11 words
The compound of claim 1 wherein R and R' are 4-chlorophenyl.
Claim 4
Dependent Claim
11 words
The compound of claim 1 wherein R and R' are 2,4-dichlorophenyl.
Claim 5
Dependent Claim
11 words
The compound of claim 1 wherein R and R' are 2,4-5-trichlorophenyl.
Claim 6
Dependent Claim
11 words
The compound of claim 1 wherein R and R' are 2,4-6-trichlorophenyl.
Claim 7
Dependent Claim
11 words
The compound of claim 1 wherein R and R' are 4-nitrophenyl.
Claim 8
Dependent Claim
11 words
The compound of claim 1 wherein R and R' are 2-methoxyethyl.
Claim 9
Dependent Claim
11 words
The compound of claim 1 wherein R and R' are 2-chloro-3-pyridyl.
Claim 10
Dependent Claim
11 words
The compound of claim 1 wherein R and R' are 2-chloroethyl.
Claim 11
Dependent Claim
52 words
A composition for reaction with a peroxide component to generate chemiluminescence comprising a mixture of a member selected from the group consisting of N,N'-bis(trifluoromethylsulfonyl)oxamide and N,N'-disubstituted derivatives thereof, with an organic fluorescer dissolved in a liquid diluent for said mixture, in proportions to produce chemiluminescence by said reaction with a peroxide component.
Claim 12
Dependent Claim
52 words
A composition for reaction with a peroxide component to generate chemiluminescence comprising a mixture of a member selected from the group consisting of N,N'-bis(trifluoromethylsulfonyl)oxamide and N,N'-disubstituted derivatives thereof, with an organic fluorescer dissolved in a liquid diluent for said mixture, in proportions to produce chemiluminescence by said reaction with a peroxide component.
Claim 13
Dependent Claim
11 words
The composition of claim 10 wherein said selected member is N,N'-bis(4-chlorophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide.
Claim 14
Dependent Claim
11 words
The composition of claim 10 wherein said selected member is N,N'-bis(2,4-dichlorophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide.
Claim 15
Dependent Claim
11 words
The composition of claim 10 wherein said selected member is N,N'-bis(2,4,5-trichlorophenyl)-T,N'-bis(trifluoromethylsulfonyl)oxamide.
Claim 16
Dependent Claim
11 words
The composition of claim 10 wherein said selected member is N,N'-bis(2,4,6-trichlorophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide.
Claim 17
Dependent Claim
11 words
The composition of claim 10 wherein said selected member is N,N'-bis(4-nitrophenyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide.
Claim 18
Dependent Claim
11 words
The composition of claim 10 wherein said selected member is N,N'-bis(2-methoxyethyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide.
Claim 19
Dependent Claim
11 words
The composition of claim 10 wherein said selected member is N,N'-bis(2-chloro-3-pyridyl)-N,N'-bis(trifluoromethylsulfonyl)oxamide.
Claim 20
Dependent Claim
16 words
A process for generating chemiluminescence comprising reacting a peroxide component with the composition of claim 10.
Claim 21
Dependent Claim
15 words
A process for generating chemiluminescence comprising reacting hydrogen peroxide with the composition of claim 10.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-10-07 | 1984-04-07 | 1984-10-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-07 | 1988-04-07 | 1988-10-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-07 | 1992-04-07 | 1992-10-07 | $7700.00 | Window Closed / Lapsed |