Non-azo 1,8-naphthalimide dyes for the detection and quantitation of a paramagnetic metal cation in a non-aqueous medium

• US 5,308,773 A
• Filed: 11/16/1992
• Issued: 05/03/1994
• Est. Priority Date: 11/16/1992
• Status: Expired due to Fees

• Current Assignee: Photobiomed Corporation
• Original Assignee: Microbiomed Corp.
• Inventors: Lewis, David E., Judy, Millard M., Utecht, Ronald E., Matthews, J. Lester
• Primary Examiner(s): Housel, James C.
• Assistant Examiner(s): Freed, Rachel
• Application Number:
  US07/977,508
• Time in Patent Office: 533 Days
• Field of Search: 436/82, 436/73, 250/302, 546/100
• US Class Current: 436/73
• CPC Class Codes: C07D 221/14 Aza-phenalenes, e.g. 1,8-naphthalimide
• CPC Class Codes: C09B 57/08 Naphthalimide dyes; Phthalimide dyes
• CPC Class Codes: G01N 21/643 non-biological material
• CPC Class Codes: G01N 31/22 using chemical indicators G01N31/02 takes precedence

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 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;

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.

2. The method according to claim 1, wherein the dye-metal cation complex consists essentially of a stoichiometric complex.

3. The method according to claim 1, wherein the non-aqueous medium is a lubricant of a mechanical system.

4. The method according to claim 1, wherein the paramagnetic metal cation is selected from the group consisting of Fe, Cr, Cu, Ni, Ce, and Mn.

5. The method 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 nm.

6. The method 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 method according to claim 1, wherein the non-azo 1,8-naphthalimide dye is a dimeric naphthalimide ring system.

8. A method for determining the presence or amount of a paramagnetic metal cation in a non-aqueous solution, comprising the steps of:

mixing a non-azo 1,8-naphthalimide dye with the paramagnetic metal cation in the non-aqueous solution to give a mixture;

irradiating the mixture with a fluorescent light sufficient to cause the mixture to emit a detectable fluorescent emission spectrum;

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 solution is a lubricant of a mechanical system.

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. A naphthalimide compound having the formula ##STR1## which comprises mixtures of stereoisomers wherein R is an aliphatic alkyl group having C=4 to C=18;

and R'"'"' is (CH₂)₂ NH₂.

17. A method for determining the presence or amount of a paramagnetic metal cation in a non-aqueous medium, comprising the steps of:

mixing a naphthalimide compound, as recited in claim 16, with the paramagnetic metal cation in the non-aqueous medium to give a mixture;

irradiating the mixture with a fluorescent light of 450 nm to cause the mixture to emit a detectable fluorescent emission spectrum;

detecting a fluorescent emission ratio of 490 to 520 nm of the mixture; and

,

monitoring differences in the detected fluorescent emission ratio of 490 to 520 nm of the mixture, as compared to standard fluorescent emission spectra ratio of 490 to 520 nm generated by reacting the naphthalimide compound, as recited in claim 16, with different known amounts of the paramagnetic metal cations, the differences being dependent upon the presence or amount of the paramagnetic metal cation present in the mixture.

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.