Chemically substituted chromophores and fluorophores of high...

Compositions – Organic luminescent material containing compositions

Reexamination Certificate

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C252S301260, C252S077000, C252S078100, C250S459100, C250S461100, C508S261000, C073S040000, C073S866000

Reexamination Certificate

active

06251302

ABSTRACT:

In many applications, visualization of fluids, fluid leakage, and the mode of fluid leakage from a system is difficult due to the clarity of the fluid and the surrounding fluid puddle. Various colored and fluorescent materials have been made as additives which allow the visualization of fluids. Currently available compounds suffer from a lack of suitable solubility in some fluids such as polyethyleneglycol based fluids.
Accordingly, what is needed is a compound that is sufficiently soluble in a fluid such that visualization of the fluid by color or fluoresence is allowed.
SUMMARY OF THE INVENTION
To overcome deficiencies in the prior art, the present invention provides, in one embodiment, a 3 or 4-amino-1,8-naphthalimide compound having polyether substituent groups at the 4-position and the imide position. The polyether groups are linked to a hydrocarbon directly linked at the 3 or 4-amino position and the imide position. The polyether groups render the 3 or 4-amino-1,8-naphthalimide compound sufficiently soluble in a fluid such that visualization of the fluid by color or fluoresence is allowed. In one advantageous embodiment, the 3 or 4-amino-1,8-naphthalimide is obtained from the mixture of 4-chloro-1,8-naphthalic anhydride with monoamine polyether.
In another embodiment, the present invention provides an amino-1,8-naphthalimide compound that is soluble in a fluid and that has substituent groups at an imide position and a position distal to said imide position. The substituent groups are linked to a hydrocarbon directly linked at the imide position and the distal position. Additionally, the substituent groups have chemical properties that render the amino-1,8-naphthalimide compound sufficiently soluble in the fluid such that visualization of the fluid by color or fluoresence is allowed.
The present invention, therefore provides in a broad scope, a colored material (chromophore) or a fluorescent material (fluorophore) compound having substituents thereon that renders the material sufficiently soluble in a fluid so that visualization of the fluid by color or fluorescence is allowed. The substituents used are chemically and physically identical or sufficiently similar in properties to the fluid that the chemical and physical forces of salvation lead to sufficient solubilization to allow detection of the dissolved colored or fluorescent material by visual or by light-detector means.
In another embodiment of the present invention, the fluid is a polyalkylene glycol lubricant, and in such embodiments, the polalkylene glycol is preferably polyethyleneglycol. In such embodiments, the 4-chloro-1,8-naphthalic anhydride may comprise about 2% by weight of the 3 or 4-amino-1,8-naphthalimide resultant product mixture and the monoamine may comprise about 98% by weight of the 3 or 4-amino-1,8-naphthalimide resultant product mixture. In another aspect of this particular embodiment, the mixture is heated to approximately 150° C. for 48 to 72 hours, and yet another aspect of the present invention, the hydrocarbon is a halogenated hydrocarbon.
In another embodiment of the present invention, the 3 or 4-amino-1,8-naphthalimide compound has the following general chemical structure:
where:
Q and Q′ are propylene;
Z and Z′ are propyl; and
n and n′ are between 9 and 10 when R and R′ are ethylmethyl; and n and n′ are between 5 and 15 when R and R′ are methyl; and where n may or may not equal n′.
One aspect of the present invention provides a 3 or 4-amino-1,8-naphthalimide compound that when added to the fluid has a excitation wavelength spectra of equal to or greater than 400 nm.
The foregoing has outlined, rather broadly, preferred and alternative features of the present invention so that those who are skilled in the art may better understand the detailed description of the invention that follows. Additional features of the invention that form the subject of the claims of the invention are described below. Those who are skilled in the art should appreciate that they can readily use the disclosed conception and specific embodiment as a basis for designing or modifying other structures for carrying out the same purposes of the present invention. Those who are skilled in the art should also realize that such equivalent constructions do not depart from the spirit and scope of the invention in its broadest form.


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