US3687673A - Color photographic light-sensitive materials containing a cyan dye for silver dye bleaching method - Google Patents

Color photographic light-sensitive materials containing a cyan dye for silver dye bleaching method Download PDF

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Publication number
US3687673A
US3687673A US74342A US3687673DA US3687673A US 3687673 A US3687673 A US 3687673A US 74342 A US74342 A US 74342A US 3687673D A US3687673D A US 3687673DA US 3687673 A US3687673 A US 3687673A
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US
United States
Prior art keywords
dye
group
cyan
silver
photographic light
Prior art date
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Expired - Lifetime
Application number
US74342A
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English (en)
Inventor
Makoto Yoshida
Shinichi Imai
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/28—Silver dye bleach processes; Materials therefor; Preparing or processing such materials
    • G03C7/29—Azo dyes therefor
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
    • C09B62/08—Azo dyes
    • C09B62/09—Disazo or polyazo dyes

Definitions

  • Patented Aug. 29, 1972 dye does not diffuse into other photographic layers and 3,687,673
  • an object of this invention is to improve the color reproducibility of color photographs by using a cyan ABSTRACT OF THE DISCLOSURE dye satisfying the above-described characteristics required
  • a color photographic lighbsensifive material for the for the dye to be used in color photographic light-sensitive Silver dye bleaching method comprising a support having materials for the silver dye bleaching method and also thereon a photographic emulsion layer containing a memhah'hg a maximum absorption Wave length at the longer ber selected from the group consisting of a cyan dye hav- Wave length sldeing the following general formula 2
  • Another object of this invention is to provide a color H0 8 SOgH OCH; H0 5 SOaH wherein X is selected from the group
  • Y is a residual group of a compound capable of reacting with the most readily reac- OF INVENTION tive chlorine atom of cyanuric chloride, and the sodium
  • X represents a halogen atom, a hydroxyl group, an amino group, or an anilino group and Y represents a (1) Fleld of the mventlon residual group of a compound capable of being reacted
  • the PWSent invention relates to a Color P g p with the first chlorine atom of cyanuric chloride. light-sensitive material for the silver dye bleaching method, wherein a cyan dye is incorporated in a photo- DESCRIPTION OF THE INVENTION sensitive silver halide emulsion layer.
  • the azo chloride the most readily replaceable chlorine atoms group of the dye must be readily reduced and decomposed described above are a hydroxyl group, :an alkoxyl in response to the amount of silver present, thereby the group, an aryloxy group, a mono-substituted amino group, dye is completely bleached.
  • the dye is incora di-substituted amino group, a nitrogen-containing cyclic porated in a silver halide emulsion, it is necessary that the group, a sulfoamino group, a thioalkyl group, and the like.
  • one of the amino groups of the H-acid which is the nuclei of a cyan dye can be in an unsubstituted state. That is to say, the maximum absorption wave elngth of an aqueous solution of dye A having the following formula Dye A:
  • the dye is not substituted at the amino group, the dye difiuses into other photographic layers when it is incorporated in a photographic emulsion layer of a color photographic lightsensitive material. This makes the utilization of the dye in color photographic light-sensitive materials difficult.
  • Dye B having the following formula prepared by substituting the amino group of H-acid with, for instance, benzoyl chloride Dye B OH NH:
  • the cyan dyes of this invention can be synthesized in the following manner. First, the first chlorine atom of the SOzH three chlorine atoms of cyanuric chloride is replaced with the residual group Y to prepare a 2-Y substituted-4,6-dichloro-S-triazine. Then, the N-substituted H-acid is synthesized by utilizing the reaction of the second chlorine atom of the substituted triazine prepared above and the amino group of H-acid. Then the N-substituted H-acid is reacted with the diazo component of a monoazo dye to obtain the cyan dye.
  • cyan dyes to be used in this invention suitable ones are those having, for example, the following structures although they are not limited to them only.
  • the sulfone group of each of the cyan dyes shown @ocrm )11 porn on sumo-Q 803E hon sour does no diffuse into other photographic emulsion layers when it is incorporated in a photographic emulsion layer of a color photographic light-sensitive material.
  • this dye shows no absorption at a longer wave region.
  • such a type of a diifusion resisting dye is therefore inadequate for a color photographic light-sensitive material. That is to say, the maximum absorption wave length of an aqueous solution of Dye B is 606 mp, which is extremely shorter than that of the dye used in this invention.
  • the inventors have investigated a cyan dye in which the amino group of the H-acid is substituted and which has the maximum absorption wave length at the wave length region of as long as possible, and have discovered that the purposes are fulfilled by the dye having the structure shown by general Formula I.
  • a cyan dye satisfying the above purposes can be obtained.
  • the cyan dyes to be used in this invention for instance dye 1 and dye 2, shown hereinafter, having extremely desirable absorption characteristics as shown in the accompanying drawing, are readily bleached, and have no adverse influence on the photographic properties of a silver halide photographic emulsion when the dye is added to the emulsion. Also, the cyan dyes have sufi'icient fastness. Thus, the cyan dyes of this invention are quite desirable as cyan dyes for color photographic light-sensitive materials in silver dye bleaching method.
  • the cyan dyes of this invention can be used not only for natural color photographic light-sensitive materials below can be substituted by a sodium atom, potassium or an ammonium group.
  • the following grouping is denoted as A:
  • typical examples of the synthesis of the cyan dyes of this invention are illustrated below.
  • a solution of 36.3 parts of sodium '1-amino-8-naphthol- 3,6-disulfonate in 200 parts of water is added to the suspension of 2-amino 4,6 dichloro S triazine prepared above.
  • the solution is heated for 45 minutes at 55 C. and then the solution is further stirred at the same temperature until the 1-amino-8-naphthol-3,6-disulfonic acid is consumed. Thereafter, the solution is neutralized by adding an aqueous 2 N sodium carbonate solution and then cooled, thereby the desired material is deposited.
  • the product is then collected by filtration and dried.
  • the precipitates are collected by filtration, washed with ethanol and dried.
  • the film was then washed with water, hardened, using a 4% aqueous formaldehyde solution, washed with water, and then processed for 15 minutes using a dye bleaching bath having the following composition:
  • the film was washed with water and then treated using a silver bleaching bath having the following composition:
  • the film was washed with Water, fixed again using the fixing bath having the composition shown above, washed further with Water, and dried.
  • the image produced was suitable as the cyan component image of a multi-color type light-sensitive material for the silver dye bleaching method.
  • EXAMPLE 2 wherein X is selected from the group consisting of a
  • X is selected from the group consisting of a
  • pound capable of reacting with the most readily reactive the image was completely blea'ched and the image was 5 chlorine atom of cyanuric chloride selected from the group suitable as the cyan component image of a multi-color consisting of a hydrpxyl group an g type light-sensitive material using a silver dye bleaching aryloxy an a S flute ammo method.
  • a color photographic silver halide light-sensitive according to claim 1, wherein said cyan dye has the material for the silver dye bleaching method comprising following formula N-i Q-OOHN on non, OH IgIH N N N-Q-N: In H0 3 305E CH3 Hogs son:
  • a support having thereon a photographic emulsion layer containing a member selected from the group consisting of a cyan dye having the following general formula:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Plural Heterocyclic Compounds (AREA)
US74342A 1969-09-22 1970-09-22 Color photographic light-sensitive materials containing a cyan dye for silver dye bleaching method Expired - Lifetime US3687673A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP44075466A JPS4910695B1 (enrdf_load_stackoverflow) 1969-09-22 1969-09-22

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US3687673A true US3687673A (en) 1972-08-29

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US (1) US3687673A (enrdf_load_stackoverflow)
JP (1) JPS4910695B1 (enrdf_load_stackoverflow)
BE (1) BE756410A (enrdf_load_stackoverflow)
CH (1) CH566579A5 (enrdf_load_stackoverflow)
DE (1) DE2046684C3 (enrdf_load_stackoverflow)
GB (1) GB1287173A (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4666805A (en) * 1984-06-19 1987-05-19 Ricoh Co., Ltd. Photosensitive material containing disazo compound for use in electrophotography
US5378817A (en) * 1992-01-22 1995-01-03 Bayer Aktiengesellschaft Reactive dyestuffs for dyeing and printing materials containing OH groups or amide groups

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0169808A3 (en) * 1984-07-24 1988-12-21 Ciba-Geigy Ag Uv-absorber compounds, method for their preparation and their use as image dyes in photographic materials for the silver dye-bleaching process

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4666805A (en) * 1984-06-19 1987-05-19 Ricoh Co., Ltd. Photosensitive material containing disazo compound for use in electrophotography
US5378817A (en) * 1992-01-22 1995-01-03 Bayer Aktiengesellschaft Reactive dyestuffs for dyeing and printing materials containing OH groups or amide groups

Also Published As

Publication number Publication date
JPS4910695B1 (enrdf_load_stackoverflow) 1974-03-12
DE2046684C3 (de) 1975-05-22
DE2046684B2 (de) 1974-10-03
CH566579A5 (enrdf_load_stackoverflow) 1975-09-15
BE756410A (fr) 1971-03-01
GB1287173A (en) 1972-08-31
DE2046684A1 (de) 1971-04-01

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