Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
2000-10-05
2001-09-11
Shah, Mukund J. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C430S468000
Reexamination Certificate
active
06288227
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to novel water-soluble 2,6-dinaphthylaminotriazines that have utility in photographic processing compositions.
BACKGROUND OF THE INVENTION
The conventional image-forming process of silver halide photography includes imagewise exposure of a photographic silver halide recording material to actinic radiation (such as actinic light), and the eventual manifestation of a useable image by wet photochemical processing of that exposed material. A fundamental step of photochemical processing is the treatment of the material with one or more developing agents to reduce silver halide to silver metal. With black-and-white photographic materials, the metallic silver usually comprises the image. With color photographic materials, the useful image consists of one or more images in organic dyes produced from an oxidized developing agent formed wherever silver halide is reduced to metallic silver.
To obtain useful color images, it is usually necessary to remove all of the silver from the photographic element after color development. This is sometimes known as “desilvering”. Removal of silver is generally accomplished by oxidizing the metallic silver, and then dissolving it and undeveloped silver halide with a “solvent” or fixing agent in what is known as a fixing step. Oxidation is achieved with an oxidizing agent, commonly known as a bleaching agent.
Fixing is typically carried out using a fixing composition that includes one or more fixing agents such as thiosulfate salts. Both ammonium and sodium thiosulfate salts are known. Fixing solutions containing ammonium ions are preferred for providing more rapid fixing, but they present environmental concerns. Thus, fixing solutions containing sodium ions, while slower, are also advantageous.
Color photographic silver halide materials often contain various sensitizing dyes that extend the inherent photosensitivity of the photosensitive silver halide emulsions to electromagnetic radiation. One important class of such sensitizing dyes are carbocyanine sensitizing dyes that are commonly included in silver halide emulsion layers in photographic silver halide films, for example in color reversal photographic silver halide films (films normally used to provide positive color images).
Many photographic silver halide elements contain residual sensitizing dyes after photoprocessing. In some cases, the level of retained sensitizing dyes is inconsequential and thus, unobservable. In other instances, however, the high level of retained sensitizing dye results in undesirably high dye stain (or unwanted color) in the elements.
The problems with residual sensitizing dyes have also been satisfactorily addressed by incorporating certain stain reducing agents into one or more working strength photographic processing compositions. These compounds are described in copending and commonly assigned U.S. Ser. No. 09/464,551 filed Dec. 16, 1999 by Goswami et al and U.S. Ser. No. 09/464,961 filed Dec. 16, 1999 by Goswami et al as colorless or slightly yellow compounds having an extended planar &pgr; system that is devoid of a diaminostilbene fragment or fused triazole nuclei. While these compounds can be incorporated into various photoprocessing compositions, it is preferred to include them in concentrated photographic fixing compositions.
However, when attempts were made to incorporate some of these stain reducing agents into concentrated processing solutions such as concentrated aqueous photographic fixing solutions, it found that several of them did not pass rigorous solubility tests. For example, many of them showed unacceptable solubility even when organic solvents were added, insolubility in solution at low temperature for lengthy times, or insolubility in concentrated fixing composition.
WO 97/10887 (Lowe et al) describes affinity ligands useful in the purification of proteins. These compounds include hundreds of possible ligands that may include 2,6-dinaphthylaminotriazines. This reference also describes some methods for making such ligands.
There remains a need for solubilized 2,6-dinaphthylaminotriazines that can be incorporated into concentrated photographic processing compositions that meet all manufacturing, customer use, and storage stability requirements.
SUMMARY OF THE INVENTION
This invention provides compounds represented by the following Structure I
wherein R is carboxy or sulfo, m is an integer of from 0 to 5 and n is an integer of from 2 to 7.
The compounds of this invention are suitably soluble in water that they can be readily incorporated into concentrated photographic processing compositions including photographic color developing, bleaching, bleach/fixing and fixing compositions without causing undesired precipitation of various components. The compounds can also be formulated and packaged in concentrated aqueous form as “additive fixer compositions”.
The compounds of Structure I also meet the following minimal stability standards that are particular to their use in photographic processing compositions:
a) they are soluble at 33 g in 500 ml of water,
b) they have low temperature solubility that is determined by placing 100 ml aqueous samples of the compounds in closed containers and holding them individually it at 0° F. (−18° C.), 20° F. (−7° C.), 30° F. (−1° C.), 40° F. (4° C.), 50° F. (10° C.) and 70° F. (21° C.) for 14 days and then observing the samples 24 hours later for signs of precipitation or other observable changes (for example color, presence of haze, or phase separation), and
c) they cause no precipitation at 33 g in a 18.9 liter volume of commercially available KODAK Fixer and Replenisher Process E-6 AR at room temperature for at least 3 days (preferably at least 10 days).
DETAILED DESCRIPTION OF THE INVENTION
The 2,6-dinaphthylaminotriazine compounds represented by Structure I have at least four sulfonate solubilizing groups attached to the naphthyl rings and specific substituents attached to the triazine ring.
The compounds of this invention are represented by Structure I:
wherein R is carboxy (or salt thereof) or sulfo (or salt thereof), m is an integer of from 0 to 5, and n is an integer of from 2 to 7. Preferably, R is carboxy, m is an integer of 1 to 2, and n is 2.
Representative compounds within Structure I are the following Compounds I-1 to I-7:
Compound I-1 (or similar potassium salt) noted above is most preferred for use in the preferred photographic fixing compositions.
These 2,6-dinaphthylaminotriazine compounds can be prepared using the methods described for example in WO 97/10887. The starting materials can be obtained from various commercial sources, including TCI-America.
In general, a preferred method includes the following reaction scheme for preparing Compound I-1 of the present invention is provided as follows:
The products can be isolated by adding acetone or acetone-methanol mixtures to the reaction mixtures. The products can also be readily characterized by conventional liquid chromatographic and mass spectra analyses.
The following examples are provided to illustrate synthesis of a preferred compound of this invention and the utility of several of the compounds, and are not to be limiting in any fashion.
REFERENCES:
patent: 3400121 (1968-09-01), Weckler et al.
patent: WO 97/10887 (1997-03-01), None
Buongiorne Jean M.
Craver Mary E.
Goswami Ramanuj
Balasubramanian Venkataraman
Eastman Kodak Company
Shah Mukund J.
Tucker J. Lanny
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