US4992381A
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Method of detecting electrolytes in an aqueous test sample using chromogenic hemispherands and test device therefor
Assignee: CALIFORNIA 2199 ADDISON ST BERKELEY CA 94720 A CORP OF, University of, Regents of
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Filing: 1987-04-15
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Granted: 1991-02-12
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Expires: 2007-04-15
Abstract
Abstract The present invention resides in the discovery of a new class of compounds defined herein as "chromogenic hemispherands" useful for the measurement of ions, in particular, ions in aqueous solution, methods of using the chromogenic hemispherands and test devices containing the chromogenic hemispherands. The chromogenic hemispherands of the invention have the structure ##STR1## wherein: R, same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; R', same or different, is lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; R", same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; Q is a chromogenic moiety capable of providing the appearance of or change in color, or which is otherwise capable of providing a detectable response in the presence of a particular cation; m is 1 to about 3; n is 0 to about 3; P is an aliphatic or aromatic subunit, e.g., --CR 2 CR 2 OCR 2 CR 2 --, ##STR2##
Inventors
- 👤 Donald J. Cram
- 👤 Eddy Chapoteau
- 👤 Bronislaw P. Czech
- 👤 Carl R. Gebauer
- 👤 Roger C. Helgeson
- 👤 Anand Kumar
- 👤 Koon-Wah Leong
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 12:07
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/08; C07D323/00; G; G01; G01N; G01N27/00; G01N27/26; G01N27/28; G01N27/30; G01N27/333; G01N27/3335
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
206 words
A method for determining cations in a sample comprising: (a) preparing a reagent mixture consisting essentially of a first organic solvent having a low vapor pressure and a high boiling point, a second organic solvent that is more volatile than said first solvent, a chromogenic hemispherand having the structure: ##STR12## wherein: R, same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; R', same or different, is lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; R", same or different, is hydrogen, lower alkyl, lower alkylidene lower alkenyl, allyl or aryl; P is an aliphatic or aromatic subunit selected from the group consisting of; --CR 2 R 2 OCR 2 CR 2 --, ##STR13## n is 0 to 3; m is 1 to 3; and Q is a chromogenic moiety capable of providing an apperance of or change in color, or other detectable response in the presence of a particular cation, and buffer; (b) adding the reagent mixture to a device consisting of a dimensionally stable, uniformly porous, diffusely reflective single or multi-layer formed of a polymeric matrix; (c) evaporating the second solvent of the reagent mixture; (d) adding the sample to the device; and (e) measuring the reflectance of the device.
Claim 2
Independent Claim
206 words
A method for determining cations in a sample comprising: (a) preparing a reagent mixture consisting essentially of a first organic solvent having a low vapor pressure and a high boiling point, a second organic solvent that is more volatile than said first solvent, a chromogenic hemispherand having the structure: ##STR12## wherein: R, same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; R', same or different, is lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; R", same or different, is hydrogen, lower alkyl, lower alkylidene lower alkenyl, allyl or aryl; P is an aliphatic or aromatic subunit selected from the group consisting of; --CR 2 R 2 OCR 2 CR 2 --, ##STR13## n is 0 to 3; m is 1 to 3; and Q is a chromogenic moiety capable of providing an apperance of or change in color, or other detectable response in the presence of a particular cation, and buffer; (b) adding the reagent mixture to a device consisting of a dimensionally stable, uniformly porous, diffusely reflective single or multi-layer formed of a polymeric matrix; (c) evaporating the second solvent of the reagent mixture; (d) adding the sample to the device; and (e) measuring the reflectance of the device.
Claim 3
Dependent Claim
30 words
The method in accordance with claim 1 in which the chromogenic moiety Q has the structure ##STR14## wherein G is a 2,4,6-trinitroanilino; 2,6-dinitro-4-trifluoromethylanilino; 2 4-dinitro-6-trifluoromethylanilino; 4-nitroanilino; 4-nitrophenylazo; 4-nitrostyryl; or 4-benzoquinonmonoimino.
Claim 4
Dependent Claim
41 words
The method in accordance with claim 2 in which the chromogenic moiety Q has the structure ##STR15## wherein: Y, same or different, is an electron withdrawing group selected from the group consisting of CN, NO 2 , CF 3 , COOR.
Claim 5
Dependent Claim
23 words
The method according to claim 1 wherein said first solvent is selected from the group consisting of trialkylphosphate, tryarylphosphate, dialkyladipate, dialkylsebacate and diakylphthalate.
Claim 6
Dependent Claim
21 words
The method according to claim 1 wherein said second solvent is selected from the group consisting of cyclohexanone, dioxane and tetrahydrofuran.
Claim 7
Dependent Claim
16 words
The method according to claim 1 wherein said buffer further includes at least one organic buffer.
Claim 8
Dependent Claim
29 words
The method according to claim 6 wherein said organic buffer is selected from the group consisting of triethanolamine, diethanolamine, ethanolamine, imidazole, 2-naphthalene sulfonic, salicylic acid and p-toluene sulfonic acid.
Claim 9
Dependent Claim
20 words
The method according to claim 1 wherein the reagent mixture has a pH of between about 7 to about 11.
Claim 10
Dependent Claim
147 words
A test device for determining the presence of an ion in aqueous solution, said device comprising a carrier matrix incorporated with a chromogenic hemispherand having the structure ##STR16## wherein: R, same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; R', same or different, is lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl R", same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; P is an aliphatic or aromatic subunit selected from the group consisting of --CR 2 R 2 OCR 2 CR 2 --, ##STR17## n is 0 to 3; m is to 1 to 3; and Q is a chromogenic moiety capable of providing an appearance of or change in color, or other detectable response in the presence of a particular cation, and a buffer to provide a pH in the range of about 7-11.
Claim 11
Dependent Claim
147 words
A test device for determining the presence of an ion in aqueous solution, said device comprising a carrier matrix incorporated with a chromogenic hemispherand having the structure ##STR16## wherein: R, same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; R', same or different, is lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl R", same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; P is an aliphatic or aromatic subunit selected from the group consisting of --CR 2 R 2 OCR 2 CR 2 --, ##STR17## n is 0 to 3; m is to 1 to 3; and Q is a chromogenic moiety capable of providing an appearance of or change in color, or other detectable response in the presence of a particular cation, and a buffer to provide a pH in the range of about 7-11.
Claim 12
Dependent Claim
27 words
The test device of claim 9 in which the chromogenic moiety Q has the structure ##STR18## wherein G is 2,4,6-trinitroanilino; 2,6-dinitro-4-trifluoromethylanilino; 2,4-dinitro-6-trifluoromethylanilino; 4-nitroanilino; 4-nitrophenylazo; 4-nitrostyryl; or 4-benzoquinonmonoimino.
Claim 13
Dependent Claim
40 words
The test device of claim 10 in which the chromogenic moiety Q has the structure ##STR19## wherein: Y, same or different, is an electron withdrawing group selected from the group consisting of CN, NO 2 , CF 3 , COOR.
Claim 14
Independent Claim
33 words
A method for determining the presence of an ion in an aqueous test sample, said method comprising contacting the sample with the device of one of claims 9-11, and observing a detectable response.
Claim 15
Independent Claim
158 words
A method for determining the presence of an ion in an aqueous test sample, said method comprising the steps of contacting said sample with a reaction mixture including a chromogenic hemispherand having the structure ##STR20## wherein: R, same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; R', same or different, is lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; R", same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; P is an aliphatic or aromatic subunit selected from the group consisting of --CR 2 R 2 OCR 2 CR 2 --, ##STR21## n is 0 to 3; m is 1 to 3; and Q is a chromogenic moiety capable of providing an appearance of or change in color, or other detectable response in the presence of a particular cation, and a buffer to provide a pH in the range of about 7-11, and observing a detectable response.
Claim 16
Independent Claim
158 words
A method for determining the presence of an ion in an aqueous test sample, said method comprising the steps of contacting said sample with a reaction mixture including a chromogenic hemispherand having the structure ##STR20## wherein: R, same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; R', same or different, is lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; R", same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl or aryl; P is an aliphatic or aromatic subunit selected from the group consisting of --CR 2 R 2 OCR 2 CR 2 --, ##STR21## n is 0 to 3; m is 1 to 3; and Q is a chromogenic moiety capable of providing an appearance of or change in color, or other detectable response in the presence of a particular cation, and a buffer to provide a pH in the range of about 7-11, and observing a detectable response.
Claim 17
Dependent Claim
26 words
The method of claim 13 in which the chromogenic moiety Q has the structure ##STR22## wherein G is 2,4,6-trinitroanilino; 2,6-dinitro-4-trifluoromethylanilino; 2,4-dinitro-6-trifluoromethylanilino; 4-nitroanilino; 4-nitrophenylazo; 4-nitrostyryl; or 4-benzoquinonmonoimino.
Claim 18
Dependent Claim
39 words
The method of claim 14 in which the chromogenic moiety Q has the structure ##STR23## wherein Y, same or different, is an electron withdrawing group selected from the group consisting of CN, NO 2 , CF 3 , COOR.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-02-11 | 1994-08-13 | 1995-02-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-02-11 | 1998-08-13 | 1999-02-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-02-11 | 2002-08-13 | 2003-02-12 | $7700.00 | Window Closed / Lapsed |