WO1994011726B1 - Non-azo 1,8-naphthalimide dyes for the detection and quantitation of a paramagnetic metal cation in a non-aqueous medium - Google Patents
Non-azo 1,8-naphthalimide dyes for the detection and quantitation of a paramagnetic metal cation in a non-aqueous mediumInfo
- Publication number
- WO1994011726B1 WO1994011726B1 PCT/US1993/010878 US9310878W WO9411726B1 WO 1994011726 B1 WO1994011726 B1 WO 1994011726B1 US 9310878 W US9310878 W US 9310878W WO 9411726 B1 WO9411726 B1 WO 9411726B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- paramagnetic metal
- azo
- dye
- fluorescent emission
- metal cation
- Prior art date
Links
- 229910052751 metal Inorganic materials 0.000 title claims abstract 25
- 239000002184 metal Substances 0.000 title claims abstract 25
- 230000005298 paramagnetic Effects 0.000 title claims abstract 24
- 150000001768 cations Chemical class 0.000 title claims abstract 20
- 238000001514 detection method Methods 0.000 title claims abstract 8
- 239000000975 dye Substances 0.000 title abstract 4
- -1 azo 1,8-naphthalimide Chemical compound 0.000 claims abstract 13
- 238000000295 emission spectrum Methods 0.000 claims abstract 12
- 239000000203 mixture Substances 0.000 claims abstract 12
- 150000002500 ions Chemical class 0.000 claims 13
- 239000003921 oil Substances 0.000 claims 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
- 238000004458 analytical method Methods 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical group C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims 3
- 229910052804 chromium Inorganic materials 0.000 claims 3
- 239000011651 chromium Substances 0.000 claims 3
- 229910052802 copper Inorganic materials 0.000 claims 3
- 239000010949 copper Substances 0.000 claims 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 3
- 229910052742 iron Inorganic materials 0.000 claims 3
- 239000000314 lubricant Substances 0.000 claims 3
- 229910052759 nickel Inorganic materials 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 229910052684 Cerium Inorganic materials 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000003086 colorant Substances 0.000 claims 2
- 238000010668 complexation reaction Methods 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 230000001809 detectable Effects 0.000 claims 2
- 230000005284 excitation Effects 0.000 claims 2
- 230000001678 irradiating Effects 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 229910052748 manganese Inorganic materials 0.000 claims 2
- 239000011159 matrix material Substances 0.000 claims 2
- 238000010791 quenching Methods 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 239000002696 acid base indicator Substances 0.000 claims 1
- 239000012491 analyte Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 230000005591 charge neutralization Effects 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- 238000004737 colorimetric analysis Methods 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 230000001419 dependent Effects 0.000 claims 1
- 238000003260 fluorescence intensity Methods 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- 229920000554 ionomer Polymers 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000010687 lubricating oil Substances 0.000 claims 1
- 230000001264 neutralization Effects 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000000171 quenching Effects 0.000 claims 1
- 238000002791 soaking Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 238000010998 test method Methods 0.000 claims 1
- 229910052718 tin Inorganic materials 0.000 claims 1
- 239000011135 tin Substances 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 238000004450 types of analysis Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Abstract
The use of a class of non-azo 1,8-naphthalimide dyes for the detection and quantitation of a paramagnetic metal cation in a non-aqueous medium and some of the dyes that will complex with a paramagnetic metal cation. The concentration of the paramagnetic metal cation is determined by monitoring differences in the detected fluorescent emission spectra of the non-azo 1,8-naphthalimide dye solution when it is mixed with paramagnetic metal cations present in the non-aqueous medium. The detected fluorescent emission spectra will vary in relation to the presence or amount of the paramagnetic metal cation in the mixture.
Claims
1. The use of a non-azo 1,8-naphthalimide dye for the detection and quantitation of a paramagnetic metal cation in a non-aqueous medium by monitoring differences of fluorescent emission spectra obtained before and upon the formation of a complex of the non-azo 1,8-naphthalimide dye and the paramagnetic metal cation.
2. The use according to claim 1, wherein the dye-metal cation complex consists essentially of a stoichiometric complex.
3. The use according to claim 1, wherein the non-aqueous medium is a lubricant of a mechanical system.
4. The use according to claim l, wherein the paramagnetic metal cation is selected from the group consisting of Fe, Cr, Cu, Ni, Ce, and Mn.
AMENDED SHEET AffflCLE 19
5. The use according to claim 1, wherein the concentration of paramagnetic metal cation is calculated using a fluorescent emission ratio of 490 to 520 nm and an excitation wavelength of about 450 n .
6. The use according to claim 1, wherein the non-azo 1,8-naphthalimide dye bears substituents at the 3 and 4 positions with the group at the 3 position capable of functioning as a leaving group.
7. The use according to claim 1, wherein the non-azo 1,8-naphthalimide dye is a dimeric naphthalimide ring system.
8. The method of using a non-azo 1,8-naphthalimide dye for the detection or quantitation of a paramagnetic metal cation in a non-aqueous medium comprising: bringing into contact the non-azo 1,8- naphthalimide dye with the paramagnetic metal cation in the non-aqueous medium to form a mixture; irradiating the mixture with a fluorescent light sufficient to cause the mixture to emit a detectable fluorescent emission spectrum; 25
detecting the fluorescent emission spectrum of the mixture; and comparing the detected fluorescent emission spectrum with standard fluorescent emission spectra generated by reacting the non-azo 1,8-naphthalimide dye with different known amounts of the paramagnetic metal cations, wherein differences between the fluorescent emission spectra compared are dependent upon the presence or amount of the paramagnetic metal cation present in the mixture.
9. The method according to claim 8, whereby the mixture comprises a dye-metal cation complex.
10. The method according to claim 9, wherein the dye-metal complex consists essentially of a stoichiometric complex.
11. The method according to claim 8, wherein the non-aqueous medium is a lubricant of a mechanical system. 26
12. The method according to claim 8, wherein the paramagnetic metal cation is selected from the group consisting of Fe, Cr, Cu, Ni, Ce, and Mn.
13. The method according to claim 8, wherein the concentration of paramagnetic metal cation is calculated using a fluorescent emission ratio of 490 to 520 nm and an excitation wavelength of about 450 nm.
14. The method according to claim 8, wherein the non-azo 1,8-naphthalimide dye bears substituents at the 3 and 4 positions with the group at the 3 position capable of functioning as a leaving group.
15. The method according to claim 8, wherein the non-azo 1,8-naphthalimide dye is a dimeric naphthalimide ring system.
16. Cancelled.
17. Cancelled. 27
18. A method for distinguishing an ion of an f-block element from an ion of a d-block element in a non- aqueous medium, comprising: mixing a non-azo 1,8-naphthalimide dye with a non- aqueous solution containing the ion of the f-block or d-block element to give a mixture; irradiating the mixture with a fluorescent light sufficient to cause the mixture to emit a detectable fluorescent emission spectrum; detecting a fluorescent emission spectrum of the mixture; and monitoring differences in the detected fluorescent emission spectrum of the mixture, as compared to standard fluorescent emission spectra generated by reacting the non-azo 1,8-naphthalimide dye with different known amounts of the ion of the f-block or d- block element, wherein the detection of quenching in the spectra indicates the presence of the ion of the f- block element.
28
STATEMENT UNDER ARTICLE 19
Applicants' Claims 1-15 and 18 are patentably distinct from the teaching of the cited references discussed below.
A. Morris (U.S.A. 4,793,977) teaches a method for the determination of the amount of acid build-up in a lubricating oil by means of an indicator test strip. The test strip involves impregnating an iono er with an acid-base indicator dye, followed by soaking the ionomer-dye matrix in strong base to convert the indicator to its base. The ionomer matrix has water of hydration and thus it is an aqueous system. The Morris test method detects the change in color of the dye on exposure to the oil, by neutralization of the water- 29
associated base in the test strip by the acid in the oil. Morris neither teaches nor implies any method for the detection or quantitation of a paramagnetic metal ion.
The method of this application is based on the complexation of paramagnetic metal ions with a non- azo-1,8-naphthalimide dye in a non-aqueous medium. In one aspect, the complexation of a paramagnetic metal ion with a non-azo-1,8-naphthalimide dye in isopropyl alcohol solution results in enhancement of fluorescent emission intensity at 495 nm, so that the detection and quantitation of paramagnetic metal ions is carried out by determining the ratio of fluorescent emission intensity at this wavelength and near 525 nm. The method claimed herein is for the analysis of paramagnetic cations in a non-aqueous medium.
B. Bertelson (U.S.A. 4,200,752) teaches 4- disubstituted amino-N-substituted naphthalimide dyestuffs. Bertelson teaches 4- dialkylaminonaphthalimides where the 4-amino nitrogen is not bonded directly to a hydrogen atom.
Further, Bertelson indicates that compounds with a hydrogen atom directly bonded to the amino 30
nitrogen do not quench, and therefore cannot be used in liquid penetrant inspections.
In contrast, all compounds claimed in this application have at least one hydrogen atom bonded directly to the 4-amino nitrogen atom.
C. Snowden, Jr. et al., (U.S.A. 4,203,725) teach a colorimetric method for the analysis of iron, copper, chromium, tin, nickel and pH in lubricant oils by examining the colors developed in aqueous solutions of indicators when the sample oil is shaken with an aqueous solution of the indicator. The colors developed by a sample are compared with those developed by a standard sample of oil containing known concentrations of the analyte. Snowden, Jr. et al. neither disclose nor suggest any method using fluorescence, nor any method involving fluorescence enhancement by paramagnetic metal ions. The method taught by Snowden, Jr. et al. is ion specific - separate analyses must be carried out for each separate ion.
The method claimed in this application is a fluorescence ratio based method for the detection and quantitation of paramagnetic metal ions in a non- 31
aqueous medium. The quantitation is carried out by determining the ratio of fluorescence intensity at two different wavelengths, and comparing that intensity to that of a standard sample. Thus, here a single reagent iε used for the analysis of all paramagnetic metal cations.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU55996/94A AU5599694A (en) | 1992-11-16 | 1993-11-12 | Non-azo 1,8-naphthalimide dyes for the detection and quantitation of a paramagnetic metal cation in a non-aqueous medium |
| GB9508605A GB2287317B (en) | 1992-11-16 | 1993-11-12 | Non-azo 1,8-naphthalimide dyes for the detection and quantitation of a paramagnetic metal cation in a non-aqueous medium |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/977,508 US5308773A (en) | 1992-11-16 | 1992-11-16 | Non-azo 1,8-naphthalimide dyes for the detection and quantitation of a paramagnetic metal cation in a non-aqueous medium |
| US07/977,508 | 1992-11-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1994011726A1 WO1994011726A1 (en) | 1994-05-26 |
| WO1994011726B1 true WO1994011726B1 (en) | 1994-07-07 |
Family
ID=25525210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1993/010878 WO1994011726A1 (en) | 1992-11-16 | 1993-11-12 | Non-azo 1,8-naphthalimide dyes for the detection and quantitation of a paramagnetic metal cation in a non-aqueous medium |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5308773A (en) |
| AU (1) | AU5599694A (en) |
| CA (1) | CA2147876A1 (en) |
| GB (1) | GB2287317B (en) |
| WO (1) | WO1994011726A1 (en) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6766183B2 (en) | 1995-11-22 | 2004-07-20 | Medtronic Minimed, Inc. | Long wave fluorophore sensor compounds and other fluorescent sensor compounds in polymers |
| US5858930A (en) * | 1997-05-30 | 1999-01-12 | United Color Manufacturing, Inc. | Liquid Benz-iso-Quinoline derivatives |
| JP3664855B2 (en) * | 1997-08-15 | 2005-06-29 | 富士ゼロックス株式会社 | Image forming method and recording medium used therefor |
| CN1328549A (en) * | 1998-11-25 | 2001-12-26 | 默克专利股份公司 | Substituted benzo [de] isoquinoline-1,3-diones |
| US5998621A (en) * | 1999-02-02 | 1999-12-07 | Milliken & Company | Aryloxy-poly(oxyalkylene) naphthalimide derivative colorants |
| US5935272A (en) * | 1999-02-02 | 1999-08-10 | Milliken & Company | Compositions comprising aryloxypolyoxyalkylene naphthalimide derivative colorants |
| US6150306A (en) * | 1999-03-04 | 2000-11-21 | Morton Internatioanl Inc. | Fluorescent tracer dyes |
| US6673625B2 (en) | 1999-09-15 | 2004-01-06 | The Regents Of The University Of California | Saccharide sensing molecules having enhanced fluorescent properties |
| US6682938B1 (en) | 1999-09-15 | 2004-01-27 | The Regents Of The University Of California | Glucose sensing molecules having selected fluorescent properties |
| AU2001251210A1 (en) * | 2000-04-04 | 2001-10-15 | Medtronic Minimed, Inc. | Saccharide sensing molecules having enhanced fluorescent properties |
| AU2002251944A1 (en) * | 2001-02-15 | 2002-09-04 | Medtronic Minimed, Inc. | Polymers functionalized with fluorescent boronate motifs |
| US7045361B2 (en) | 2001-09-12 | 2006-05-16 | Medtronic Minimed, Inc. | Analyte sensing via acridine-based boronate biosensors |
| US7378281B2 (en) * | 2002-03-08 | 2008-05-27 | The United States Of America As Represented By The Secretary Of The Navy | Process to measure PPB levels of dissolved copper in jet fuels and other non-aqueous fluids using a colorimetric process |
| JP5893478B2 (en) * | 2012-03-30 | 2016-03-23 | 出光興産株式会社 | Lubricating oil composition for refrigerator |
| EP2853884A1 (en) * | 2013-09-25 | 2015-04-01 | Siemens Aktiengesellschaft | A technique for determining metals in oil samples obtained from lubricating oil of machines |
| CN118050338B (en) * | 2024-02-06 | 2024-09-24 | 安庆师范大学 | Application of azo compound as fluorescent probe in detection of ferric ions |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR753104A (en) * | 1932-03-24 | 1933-10-07 | Ig Farbenindustrie Ag | Process for the preparation of 4-amino-1, 8-naphthalene-dicarboxylic acid imide and its derivatives |
| US2415373A (en) * | 1942-09-05 | 1947-02-04 | American Cyanamid Co | Substituted 4-hydroxyalkylamino-1, 8-naphthalic acid imides |
| BE792723A (en) * | 1971-12-15 | 1973-06-14 | Merck Patent Gmbh | INDICATOR TO DETECT METAL IONS |
| US3965350A (en) * | 1972-01-24 | 1976-06-22 | Air Products And Chemicals, Inc. | Dye penetrant method for detecting flows |
| SU491615A1 (en) * | 1973-09-13 | 1975-11-15 | Предприятие П/Я А-7815 | Metallo-fluorescent / titrating agents ethylene diamine-di- / 1 / methylene-2-hydroxyaphthyl / -diacetic acid |
| US4203725A (en) * | 1978-02-13 | 1980-05-20 | Contamoil Corporation | Method and test kit for the on-site determination of the presence of contaminant material in lubricating oil |
| US4200752A (en) * | 1978-02-16 | 1980-04-29 | Bertelson Robert C | 4-Disubstituted amino, N-substituted naphthalimide dyestuffs |
| GB2183667B (en) * | 1985-10-29 | 1989-11-22 | Univ Brunel | Preparation of amino-1;8-naphthalimides. |
| US4793977A (en) * | 1987-04-09 | 1988-12-27 | Cape Cod Research, Inc. | Colorimetric detector for monitoring oil degradation |
| US4876206A (en) * | 1989-02-10 | 1989-10-24 | Sayer Wayne L | Methods for detecting rare earth minerals |
| US5126272A (en) * | 1989-03-02 | 1992-06-30 | United States Of America | System for detecting transition and rare earth elements in a matrix |
| US5235045A (en) * | 1992-03-19 | 1993-08-10 | Microbiomed Corporation | Non-azo naphthalimide dyes |
-
1992
- 1992-11-16 US US07/977,508 patent/US5308773A/en not_active Expired - Fee Related
-
1993
- 1993-11-12 CA CA002147876A patent/CA2147876A1/en not_active Abandoned
- 1993-11-12 AU AU55996/94A patent/AU5599694A/en not_active Abandoned
- 1993-11-12 GB GB9508605A patent/GB2287317B/en not_active Expired - Lifetime
- 1993-11-12 WO PCT/US1993/010878 patent/WO1994011726A1/en active Application Filing
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