US3459552A - Silver halide emulsions containing magenta-colored cyan couplers - Google Patents

Silver halide emulsions containing magenta-colored cyan couplers Download PDF

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Publication number
US3459552A
US3459552A US523686A US3459552DA US3459552A US 3459552 A US3459552 A US 3459552A US 523686 A US523686 A US 523686A US 3459552D A US3459552D A US 3459552DA US 3459552 A US3459552 A US 3459552A
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Prior art keywords
coupler
color
couplers
silver halide
hydroxy
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Expired - Lifetime
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US523686A
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English (en)
Inventor
Makoto Yoshida
Akio Okumura
Keisuke Shiba
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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
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32—Colour coupling substances
    • G03C7/333—Coloured coupling substances, e.g. for the correction of the coloured image
    • G03C7/3335—Coloured coupling substances, e.g. for the correction of the coloured image containing an azo chromophore
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/24—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by surface fusion and bonding of particles to form voids, e.g. sintering

Definitions

  • R is a mononuclear aryl radical substituted with at least one alkoxycarbonyl group having at least 9 carbon atoms; and R is a lower alkyl group.
  • the present invention relates to color photography and particularly color photographic materials containing improved colored couplers.
  • cyan couplers used as color formers in color photography are l-naphthl-2-carb0xylic acid derivatives or aminophenol derivatives.
  • a long-chain alkyl group or a dialkylphenoxy group is introduced into the coupler molecule as a group for giving diffusion resistance to the couple-r.
  • an aryl group is introduced into the 2-position of the naphthol nucleus of a cyan colored coupler, as a method for improving the color, solubility in water-insoluble, high boiling point solvents (hereinafter these solvents are called simply coupler solvents) is lowered.
  • couplers having a branched alkyl group at the 2-position of the naphthol nucleus as couplers having good solubility in coupler solvents, and being easily prepared.
  • Couplers have a very long wave length absorption maximum of 505 to 510 m
  • cyan colored couplers having the longer wave length absorption maximum and a large green absorption are more profitable in color correction.
  • magenta-colored cyan couplers which have sufiicient solubility in coupler solvents, and which are prepared by using inexpensive materials and simple procedures.
  • a further object is to provide magenta-colored cyan couplers having bathochromic absorption maximum and a large green absorption.
  • couplers in which one or more higher alkoxycarbonyl groups are introduced to the aryl group at the 2-position of the naphthol nucleus according to this invention.
  • couplers of this invention are selected from the group consisting of compounds with the general formula:
  • each of the couplers is dissolved in tricresyl N 3 phosphate, the optical absorption curves are measured and they are plotted in the figures by setting the maxi- I mum optical density to 1.0.
  • Curve (A) is the spectroscopic absorption curve of Coupler (I) of this invention, Curve (B) that of above-mentioned comparative Coupler (a) and Curve (C) that of comparative Coupler (0) described in Japanese Patent No. 508,680.
  • the couplers of this invention have maximum absorption at longer wave length than CONHCHZOmCHmCH that of the coupler described in Japanese Patent No. O 508,680, which is very profitable in color correction effect. Furthermore, the maximum absorption of the (30m coupler of this invention is at a little longer wave length than those of the coupler having an aryl group at the 2-position of the naphthol nucleus, but having a longchain alkyl group bonded to the aryl group by an acid Q amide bond and the couplers having no substituents at the aryl group. Accordingly, the introduction of a higher (30002115 (b) alkoxycarbonyl group to the aryl radical at the 2-position OH r of the naphthol nucleus is profitable in this point also.
  • the product was mixed with 1,000 ml. of methanol and cooled to form crystals, which were collected by filtration and rinsed with 200 ml. of methanol.
  • the recrystallization from methanol gave 221 g. (yield 73%) of the product.
  • the melting point of the product was 82-84" C.
  • the product was dissolved in 300 ml. of ethanol and the solution was cooled by ice to precipitate crystals, which were collected by filtration and rinsed with 100 ml. of methanol.
  • the thus obtained diazonium salt solution was added at temperatures of below 8 C. in a solution of 24 g. of the l-hydroxy-2-(4 -dodecyloxycarbonyl) naphthanilide, obtained by above-mentioned (l-B), in 400 ml. of pyridine to conduct coupling and the thus precipitated crystals were collected by filtration, rinsed with 1,000 m1. of water containing 50 ml. of hydrochloric acid and further 2,000 ml. of water, recrystallized from 500 ml. of diethyl formamide, and then rinsed with 100 ml. of methanol. By the treatment, 30 g. (yield 91%) of the coupler was obtained. The melting point of the coupler was 165l66 C. and the analytical value of nitrogen was 6.26% (calculated 6.46%
  • EXAMPLE 1 Into 10 parts of tricresyl phosphate was dissolved 1.25 parts of the coupler having structure (I) by heating to 80 C. and the solution was mixed with 100 parts of an aqueous 10% gelatin solution pre-heated to 60 C. The solution was further mixed with 2 parts of-an aqueous 10% solution of sodium alkylbenzene sulfonate and the system was stirred for 5 minutes by using a high speed rotary mixer at about 65 C. with an interruption of 1 minute, the stirring being repeated 5 times to give an emulsified dispersion of the coupler.
  • the film was exposed to red light using an optical wedge and developed as usual in a color developing solution having the following composition:
  • the film was exposed to red light using an optical wedge, developed, bleached and fixed as in Example 1 to give a positive red image having very excellent transparency and a cyan-colored negative image.
  • the maximum absorption wave length thereof is shown in the following table.
  • Example 2 Example 3
  • Example 3 Example 3
  • the dispersion was mixed with a silver halide light-sensitive emulsion and coated on a film base as in Example 1 to give a red-sensitive color photographic light-sensitive material.
  • the photographic film was then exposed, colordeveloped, bleached and fixed to give a positive red image having very excellent transparency and a cyan-colored negative image.
  • a color photographic silver halide emulsion containing a color coupler having the following general formula:
  • the color photographic silver halide emulsion as 13 The color photographic silver halide emulsion as claimed in claim 1 wherein said color coupler is claimed in claim 1 wherein said color coupler is OH COO(CH2)11CH3 c2115 CONH- 5 OH coocmomcmmrr, ⁇ J I CQNHQ @J ooocrHr 12.
  • the color photographic silver halide emulsion as claimed in claim 1 wherein said color coupler is 00002115 OH COO(CH2)1CH3
  • said color coupler is 00002115 OH COO(CH2)1CH3

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US523686A 1965-02-03 1966-01-28 Silver halide emulsions containing magenta-colored cyan couplers Expired - Lifetime US3459552A (en)

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JP566465 1965-02-03

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US3459552A true US3459552A (en) 1969-08-05

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US (1) US3459552A (en])
BE (1) BE675931A (en])
CH (1) CH466709A (en])
DE (1) DE1547831A1 (en])
GB (1) GB1111342A (en])

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3615225A (en) * 1967-12-21 1971-10-26 Agfa Gevaert Ag Color photographic material
US3619196A (en) * 1968-10-24 1971-11-09 Konishiroku Photo Ind Light-sensitive color-photographic emulsions
US3784383A (en) * 1969-04-14 1974-01-08 Konishiroku Photo Ind Light sensitive silver halide color photographic material
US3844795A (en) * 1971-05-07 1974-10-29 Agfa Gevaert Ag Silver halide photographic material containing azo masking couplers
US5506094A (en) * 1993-07-28 1996-04-09 Eastman Kodak Company Photographic elements comprising 2-phenylcarbamoyl-1-naphthol image-modifying couplers yielding dyes resistant to crystallization and reduction
US5510235A (en) * 1993-07-28 1996-04-23 Eastman Kodak Company Photographic elements comprising 2-phenylcarbamoyl-naphthol image-modifying couplers yielding dyes resistant to crystallization and reduction
US5514530A (en) * 1993-07-28 1996-05-07 Eastman Kodak Company Photographic elements comprising 2-phenylcarbamoyl-1-naphthol image-modifying couplers yielding dyes resistant to crystallization and reduction
US5521057A (en) * 1993-07-28 1996-05-28 Eastman Kodak Company Photographic elements comprising 2-phenylcarbamoyl-1-naphthol image-modifying couplers yeilding dyes resistant to crystallization and reduction

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05100374A (ja) * 1991-10-08 1993-04-23 Fuji Photo Film Co Ltd シアン色素形成カプラー及びこれを含むハロゲン化銀カラー写真感光材料

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2521908A (en) * 1947-03-13 1950-09-12 Eastman Kodak Co 1-hydroxy-2-naphthamide colored couplers
US2706684A (en) * 1952-11-28 1955-04-19 Eastman Kodak Co 1-hydroxy-2-naphthamide colored couplers
US2808329A (en) * 1954-11-22 1957-10-01 Eastman Kodak Co Photographic color correction using colored and uncolored couplers
US3034892A (en) * 1958-10-27 1962-05-15 Eastman Kodak Co Magenta-colored cyan-forming couplers

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2521908A (en) * 1947-03-13 1950-09-12 Eastman Kodak Co 1-hydroxy-2-naphthamide colored couplers
US2706684A (en) * 1952-11-28 1955-04-19 Eastman Kodak Co 1-hydroxy-2-naphthamide colored couplers
US2808329A (en) * 1954-11-22 1957-10-01 Eastman Kodak Co Photographic color correction using colored and uncolored couplers
US3034892A (en) * 1958-10-27 1962-05-15 Eastman Kodak Co Magenta-colored cyan-forming couplers

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3615225A (en) * 1967-12-21 1971-10-26 Agfa Gevaert Ag Color photographic material
US3619196A (en) * 1968-10-24 1971-11-09 Konishiroku Photo Ind Light-sensitive color-photographic emulsions
US3784383A (en) * 1969-04-14 1974-01-08 Konishiroku Photo Ind Light sensitive silver halide color photographic material
US3844795A (en) * 1971-05-07 1974-10-29 Agfa Gevaert Ag Silver halide photographic material containing azo masking couplers
US5506094A (en) * 1993-07-28 1996-04-09 Eastman Kodak Company Photographic elements comprising 2-phenylcarbamoyl-1-naphthol image-modifying couplers yielding dyes resistant to crystallization and reduction
US5510235A (en) * 1993-07-28 1996-04-23 Eastman Kodak Company Photographic elements comprising 2-phenylcarbamoyl-naphthol image-modifying couplers yielding dyes resistant to crystallization and reduction
US5514530A (en) * 1993-07-28 1996-05-07 Eastman Kodak Company Photographic elements comprising 2-phenylcarbamoyl-1-naphthol image-modifying couplers yielding dyes resistant to crystallization and reduction
US5521057A (en) * 1993-07-28 1996-05-28 Eastman Kodak Company Photographic elements comprising 2-phenylcarbamoyl-1-naphthol image-modifying couplers yeilding dyes resistant to crystallization and reduction

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Publication number Publication date
GB1111342A (en) 1968-04-24
DE1547831A1 (de) 1970-03-19
CH466709A (de) 1968-12-15
BE675931A (en]) 1966-06-16

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