US4089747A
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US
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Compositions for the detection of hydrogen peroxide
Assignee: Eastman Kodak Co
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Filing: 1976-08-09
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Granted: 1978-05-16
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Expires: 1996-08-09
Abstract
Abstract There are disclosed buffered compositions for detecting either hydrogen peroxide or a substance having peroxidative activity by the catalytic oxidation of a dye-providing material by hydrogen peroxide in the presence of the material having peroxidative activity, which compositions comprise (A) hydrogen peroxide or substance having peroxidative activity, as appropriate, and (B) as the dye-providing material, either (I) a mixture of (A) EITHER A SULFONYL HYDRAZONE OF THE FORMULA <IMAGE> or a sulfonyl hydrazone precursor of the formula <IMAGE> wherein R = alkyl R' = hydrogen, aryl, alkoxy, halogen or alkyl R'' = aryl or alkyl Z = atoms necessary to complete a heterocyclic ring of 5-6 atoms in the ring nucleus M(-) = AN ANION; AND (B) A COUPLER OR (II) a triarylimidazole of the formula <IMAGE> wherein R1, R2 and R3 are each an organic group such that at least one of R1, R2 and R3 is an ortho or para hydroxy substituted aryl group of up to 18 carbon atoms; the other two R1, R2 and R3 being chosen such that the oxidation potential of the imidazole lies between -70 mV to +110 mV measured by cyclic voltometry against a standard calomel electrode using a carbon based electrode.
Inventors
- 👤 Barbara Jungfleisch Bruschi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 16:50
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/64; C12; C12Q; C12Q1/00; C12Q1/26; C12Q1/28; G; G03; G03C; G03C7/00; G03C7/30; G03C7/32; G03C7/36; G03C7/38; G03C7/381; G03C7/3815; C12Q2326/00; Y; Y10; Y10S; Y10S435/00; Y10S435/805; Y10T; Y10T436/00; Y10T436/14; Y10T436/142222; Y10T436/143333; Y10T436/144444; Y10T436/145555; Y10T436/147777; Y10T436/148888; Y10T436/20; Y10T436/206664
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
143 words
In a composition for the determination of hydrogen peroxide in aqueous solution, said composition comprising a substance having peroxidative activity and a dye-providing material which undergoes a detectable change upon contact with hydrogen peroxide and the substance having peroxidative activity, the improvement wherein the dye-providing material comprises: a triarylimidazole of the formula ##STR37## wherein R 1 , R 2 , and R 3 are each an organic group such that at least one of R 1 , R 2 , and R 3 is an ortho or para hydroxy substituted aryl group of up to 18 carbon atoms; the other two R 1 , R 2 , and R 3 being aryl groups chosen such that the oxidation potential of the imidazole lies between -70 mV to +110 mV measured by cyclic voltometry against a standard calomel electrode using a carbon based electrode.
Claim 2
Dependent Claim
143 words
In a composition for the determination of hydrogen peroxide in aqueous solution, said composition comprising a substance having peroxidative activity and a dye-providing material which undergoes a detectable change upon contact with hydrogen peroxide and the substance having peroxidative activity, the improvement wherein the dye-providing material comprises: a triarylimidazole of the formula ##STR37## wherein R 1 , R 2 , and R 3 are each an organic group such that at least one of R 1 , R 2 , and R 3 is an ortho or para hydroxy substituted aryl group of up to 18 carbon atoms; the other two R 1 , R 2 , and R 3 being aryl groups chosen such that the oxidation potential of the imidazole lies between -70 mV to +110 mV measured by cyclic voltometry against a standard calomel electrode using a carbon based electrode.
Claim 3
Dependent Claim
85 words
The composition of claim 1 wherein the dye providing material contains a triarylimidazole of the formula ##STR38## wherein R 1 , R 2 and R 3 are each aryl or substituted aryl groups of up to 18 carbon atoms, such that at least one of R 1 , R 2 and R 3 is an ortho or para hydroxy substituted aryl group; and at least one other of R 1 , R 2 and R 3 has an ortho or para electron donating substituent group.
Claim 4
Dependent Claim
59 words
The composition of claim 2 wherein the ortho or para electron donating substituent group is an alkoxy group having the formula --OR wherein R is an alkyl group of 1 to about 8 carbon atoms, an aryloxy group or a dialkylamino group having the formula ##STR39## wherein R is an alkyl group of 1 to about 8 carbon atoms.
Claim 5
Dependent Claim
29 words
The composition of claim 1 wherein dyeproviding material contains a triarylimidazole selected from the group consisting of: 2-(4-hydroxy-3,5-dimethoxyphenyl)4,5-bis(4-methoxyphenyl)-imidazole; 2-(3,5-dibromo-4-hydroxyphenyl)4,5-diphenylimidazole; 2-(3-bromo-5-methoxy-4-hydroxyphenyl)-4,5-bis(4-methoxyphenyl)-imidazole; 4,5-bis (4-dimethylaminophenyl)-2-(4-hydroxyphenyl)-imidazole; 4,5-bis (4-dimethylaminophenyl)-2-(4-hydroxy-3-methoxyphenyl) imidazole; 2-(4-hydroxyphenyl)4,5-bis(4-methoxyphenyl) imidazole; and 4,5-bis(4-dimethylaminophenyl)-2-(4-hydroxy)3,5-dimethoxyphenyl)imidazole.
Claim 6
Dependent Claim
159 words
In a composition for the detection of uric acid in aqueous solution, said composition comprising uricase, buffer, substance having peroxidative activity and a dye-providing material which undergoes a detectable change upon contact with hydrogen peroxide, in the presence of the substance having peroxidative activity, said hydrogen peroxide produced by the action of uricase of uric acid, the improvement wherein the dye-providing material comprises: a triarylimidazole of the formula ##STR40## wherein R 1 , R 2 , and R 3 are each an organic group such that at least one of R 1 , R 2 , and R 3 is an ortho or para hydroxy substituted aryl group of up to 18 carbon atoms; the other two R 1 , R 2 , and R 3 being aryl groups chosen such that the oxidation potential of the imidazole lies between -70 mV to +100 mV measured by cyclic voltometry against a standard calomel electrode using a carbon based electrode.
Claim 7
Dependent Claim
159 words
In a composition for the detection of uric acid in aqueous solution, said composition comprising uricase, buffer, substance having peroxidative activity and a dye-providing material which undergoes a detectable change upon contact with hydrogen peroxide, in the presence of the substance having peroxidative activity, said hydrogen peroxide produced by the action of uricase of uric acid, the improvement wherein the dye-providing material comprises: a triarylimidazole of the formula ##STR40## wherein R 1 , R 2 , and R 3 are each an organic group such that at least one of R 1 , R 2 , and R 3 is an ortho or para hydroxy substituted aryl group of up to 18 carbon atoms; the other two R 1 , R 2 , and R 3 being aryl groups chosen such that the oxidation potential of the imidazole lies between -70 mV to +100 mV measured by cyclic voltometry against a standard calomel electrode using a carbon based electrode.
Claim 8
Dependent Claim
81 words
The composition of claim 5 wherein the dye-providing material contains triarylimidazole of the formula ##STR41## wherein R 1 , R 2 and R 3 are each an aryl group of up to 18 carbon atoms, such that at least one of R 1 , R 2 or R 3 is an ortho or para hydroxy substituted aryl group and at least one other of R 1 , R 2 and R 3 has an ortho or para electron donating substituent group.
Claim 9
Dependent Claim
57 words
The composition of claim 5 wherein the ortho or para electron donating substituent group is an alkoxy group having the formula --OR wherein R is an alkyl group of from 1 to about 8 carbon atoms, an aryloxy group or a dialkylamino group having the formula: ##STR42## wherein R is an alkyl group of 1-8 carbon atoms.
Claim 10
Dependent Claim
28 words
The composition of claim 6 wherein the dye-providing material contains a triarylimidazole selected from the group consisting of: 2-(4-hydroxy-3,5-dimethoxyphenyl)-4,5-bis(4-methoxyphenyl)-imidazole; 2-(3,5-dibromo-4-hydroxyphenyl)4,5-diphenylimidazole; 2-(3-bromo-5-methoxy-4-hydroxyphenyl)-4,5-bis(4-methoxyphenyl)-imidazole; 4,5-bis(4-dimethylaminophenyl)-2-(4-hydroxyphenyl)-imidazole; 4,5-bis(4-dimethylaminophenyl)-2-(4-hydroxy-3-methoxyphenyl) imidazole; 2-(4-hydroxyphenyl)-4,5-bis(4-methoxyphenyl) imidazole; and 4,5-bis(4-dimethylzminophenyl)-2-(4-hydroxy)3,5-dimethoxyphenyl)imidazole.
Claim 11
Dependent Claim
147 words
A composition for the assay of aqueous liquid for a predetermined analyte comprising (a) an enzyme which effects the production of hydrogen peroxide upon contact with said analyte and (b) a hydrogen peroxide detection composition comprising (I) a substance having peroxidative activity, (II) a buffer, (III) a dye-providing material which is a triarylimidazole of the formula ##STR43## wherein R 1 , R 2 , and R 3 are each an organic group such that at least one of R 1 , R 2 , and R 3 is an ortho or para hydroxy substituted aryl group of up to 18 carbon atoms; the other two R 1 , R 2 , and R 3 being aryl groups chosen such that the oxidation potential of the imidazole lies between -70 mV to +100 mV measured by cyclic voltometry against a standard calomel electrode using a carbon based electrode.
Claim 12
Dependent Claim
147 words
A composition for the assay of aqueous liquid for a predetermined analyte comprising (a) an enzyme which effects the production of hydrogen peroxide upon contact with said analyte and (b) a hydrogen peroxide detection composition comprising (I) a substance having peroxidative activity, (II) a buffer, (III) a dye-providing material which is a triarylimidazole of the formula ##STR43## wherein R 1 , R 2 , and R 3 are each an organic group such that at least one of R 1 , R 2 , and R 3 is an ortho or para hydroxy substituted aryl group of up to 18 carbon atoms; the other two R 1 , R 2 , and R 3 being aryl groups chosen such that the oxidation potential of the imidazole lies between -70 mV to +100 mV measured by cyclic voltometry against a standard calomel electrode using a carbon based electrode.
Claim 13
Dependent Claim
82 words
The composition of claim 9 wherein the dye-providing material contains a triarylimidaxole of the formula ##STR44## wherein R 1 , R 2 and R 3 are each an aryl group of up to 18 carbon atoms, such that at least one of R 1 , R 2 and R 3 is an ortho or para hydroxy substituted aryl group; and at least one other of R 1 , R 2 and R 3 has an ortho or para electron donating substituent group.
Claim 14
Dependent Claim
60 words
The composition of claim 10 wherein the ortho or para electron donating substituent group is an alkoxy group having the formula --OR where R is an alkyl group of from 1 to about 8 carbon atoms, an aryloxy group of a dialkylamino group having the formula ##STR45## wherein R is an alkyl group of 1 to about 8 carbon atoms.
Claim 15
Dependent Claim
28 words
The composition of claim 9 wherein the dye-providing material contains a triarylimidazole selected from the group consisting of: 2-(4-hydroxy-3,5-dimethoxyphenyl)-4,5-bis(4-methoxyphenyl)-imidazole; 2-(3,5-dibromo-4-hydroxyphenyl)4,5-diphenylimidazole; 2-(3-bromo-5-methoxy-4-hydroxyphenyl)-4,5-bis(4-methoxyphenyl)-imidazole; 4,5-bis(4-dimethylaminophenyl)-2-(4-hydroxyphenyl)-imidazole; 4,5-bis(4-dimethylaminophenyl)-2-(4-hydroxy-3-methoxyphenyl) imidazole; 2-(4-hydroxyphenyl)4,5-bis(4-methoxyphenyl) imidazole; and 4,5-bis(4-dimethylaminophenyl)-2-(4-hydroxy)3,5-dimethoxyphenyl)imidazole.
Claim 16
Dependent Claim
157 words
In a method for assaying an aqueous liquid for hydrogen peroxide content comprising contacting a sample of the aqueous liquid with a buffered composition comprising a substance having peroxidative activity and a dye-providing material which is oxidized in the presence of hydrogen peroxide and said substance having peroxidative activity to provide a dye, the improvement comprising using as the dye-providing material ##STR46## a triarylimidazole of the formula ##STR47## wherein R 1 , R 2 , R 3 are each an organic group such that at least one of R 1 , R 2 , and R 3 is an ortho or para hydroxy substituted aryl group of up to 18 carbon atoms; the other two R 1 , R 2 , and R 3 are aryl groups chosen such that the oxidation potential of the imidazole lies between -70 mV to +110 mV measured by cyclic voltometry against a standard calomel electrode using a carbon based electrode.
Claim 17
Dependent Claim
157 words
In a method for assaying an aqueous liquid for hydrogen peroxide content comprising contacting a sample of the aqueous liquid with a buffered composition comprising a substance having peroxidative activity and a dye-providing material which is oxidized in the presence of hydrogen peroxide and said substance having peroxidative activity to provide a dye, the improvement comprising using as the dye-providing material ##STR46## a triarylimidazole of the formula ##STR47## wherein R 1 , R 2 , R 3 are each an organic group such that at least one of R 1 , R 2 , and R 3 is an ortho or para hydroxy substituted aryl group of up to 18 carbon atoms; the other two R 1 , R 2 , and R 3 are aryl groups chosen such that the oxidation potential of the imidazole lies between -70 mV to +110 mV measured by cyclic voltometry against a standard calomel electrode using a carbon based electrode.
Claim 18
Dependent Claim
84 words
The method of claim 13 wherein the dye-providing material contains a triarylimidazole of the formula ##STR48## wherein R 1 , R 2 and R 3 are each aryl or substituted aryl groups of up to 18 carbon atoms, such that at least one of R 1 , R 2 and R 3 is an ortho or para hydroxy substituted aryl group; and at least one other of R 1 , R 2 and R 3 has an ortho or para electron donating substituent group.
Claim 19
Dependent Claim
58 words
The method of claim 14 wherein the ortho or para electron donating substituent group is an alkoxy group having the formula --OR where R is an alkyl group of from 1 to about 8 carbon atoms, an aryloxy group or a dialkylamino group ##STR49## wherein R is an alkyl group of from 1 to about 8 carbon atoms.
Claim 20
Dependent Claim
27 words
The composition of claim 14 wherein dye-providing material contains a triarylimidazole selected from the group consisting of: 2-(4-hydroxy-3,5-dimethoxyphenyl)-4,5-bis(4-methoxyphenyl)-imidazole; 2-(3,5-dibromo-4-hydroxyphenyl)4,5-diphenylimidazole; 2-(3-bromo-5-methoxy-4-hydroxyphenyl)-4,5-bis(4-methoxyphenyl)-imidazole; 4,5-bis(4-dimethylaminophenyl)-2-(4-hydroxyphenyl)-imidazole; 4,5-bis(4-dimethylaminophenyl)-2-(4-hydroxy-3-methoxyphenyl) imidazole; 2-(4-hydroxyphenyl)4,5-bis(4-methoxyphenyl) imidazole; and 4,5-bis(4dimethylaminphenyl)-2-(4-hydroxy)3,5-dimethoxyphenyl)imidazole.
Claim 21
Dependent Claim
148 words
An element for the detection of uric acid in aqueous liquid, the element comprising a non-fibrous, isotropically porous spreading layer and a reagent layer and containing (a) uricase and (b) a hydrogen peroxide detection composition comprising (I) a substance having peroxidative activity, (II) a buffer, (III) and a dye-providing material which is a triarylimidazole of the formula t,680 wherein R 1 , R 2 , and R 3 are each an organic group such that at least one of R 1 , R 2 , and R 3 is an ortho or para hydroxy substituted aryl group of up to 18 carbon atoms; the other two R 1 , R 2 , and R 3 being aryl groups chosen such that the oxidation potential of the imidazole lies between -70 mV to +110 mV measured by cyclic voltometry against a standard calomel electrode using a carbon based electrode.
Claim 22
Dependent Claim
148 words
An element for the detection of uric acid in aqueous liquid, the element comprising a non-fibrous, isotropically porous spreading layer and a reagent layer and containing (a) uricase and (b) a hydrogen peroxide detection composition comprising (I) a substance having peroxidative activity, (II) a buffer, (III) and a dye-providing material which is a triarylimidazole of the formula t,680 wherein R 1 , R 2 , and R 3 are each an organic group such that at least one of R 1 , R 2 , and R 3 is an ortho or para hydroxy substituted aryl group of up to 18 carbon atoms; the other two R 1 , R 2 , and R 3 being aryl groups chosen such that the oxidation potential of the imidazole lies between -70 mV to +110 mV measured by cyclic voltometry against a standard calomel electrode using a carbon based electrode.
Claim 23
Dependent Claim
81 words
The element of claim 17 wherein the dye-providing material contains a triarylamidazole of the formula ##STR50## wherein R 1 , R 2 and R 3 are each aryl groups of up to 18 carbon atoms, such that at least one of R 1 , R 2 and R 3 is an ortho or para hydroxy substituted aryl group; and at least one other of R 1 , R 2 and R 3 has an ortho or para electron donating substituent group.
Claim 24
Dependent Claim
53 words
The element of claim 18 wherein the ortho or para electron donating substituent group is an alkoxy group --OR where R is an alkyl group of 1 to about 8 carbon atoms, an aryloxy group or a dialkylamino group ##STR51## wherein R is an alkyl group of 1 to about 8 carbon atoms.
Claim 25
Dependent Claim
28 words
The element of claim 18 wherein the dye-providing material contains a triarylimidazole selected from the group consisting of: 2-(4-hydroxy-3,5-dimethoxyphenyl)4,5-bis(4-methoxyphenyl)-imidazole; 2-(3,5-dibromo-4-hydroxyphenyl)4,5-diphenylimidazole; 2-(3-bromo-5-methoxy-4-hydroxyphenyl)-4,5-bis(4-methoxyphenyl)-imidazole; 4,5-bis(4-dimethylaminophenyl)-2-(4-hydroxphenyl)-imidazole; 4,5-bis(4-dimethylaminophenyl)-2-(4-hydroxy-3-methoxyphenyl) imidazole; 2-(4-hydroxyphenyl)4,5-bis(4-methoxyphenyl) imidazole; and 4,5-bis(4-dimethylaminophenyl)-2-(4-hydroxy)3,5-dimethoxyphenyl)imidazole.
References Cited (Backward Citations)
US3297710A
Cited
US3630847A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-15 | 1981-11-14 | 1982-05-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-15 | 1985-11-14 | 1986-05-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-15 | 1989-11-14 | 1990-05-16 | $7700.00 | Window Closed / Lapsed |