US3844795A - Silver halide photographic material containing azo masking couplers - Google Patents

Silver halide photographic material containing azo masking couplers Download PDF

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US3844795A
US3844795A US00250300A US25030072A US3844795A US 3844795 A US3844795 A US 3844795A US 00250300 A US00250300 A US 00250300A US 25030072 A US25030072 A US 25030072A US 3844795 A US3844795 A US 3844795A
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silver halide
couplers
cyan
red
masking
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US00250300A
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D Kalz
W Puschel
G Benoy
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Agfa Gevaert AG
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Agfa Gevaert AG
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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
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series

Definitions

  • red cyan coupler has advantageous properties with respect to suitable absorption dyes, efficient emulsifiability and excellent reactivity.
  • the invention relates to a color photographic material with improved color reproduction which contains red cyan couplers for the production of so-called builtin masks, preferably in an emulsified form.
  • the image dye is formed in the exposed and developed areas while in the unexposed areas the color of the colored coupler used is preserved.
  • the gradation of unwanted side densities obtained in the course of processing is compensated by an equal but opposite gradation of the masking dye so that the density in the unwanted region of the spectrum is uniform regardless of the conditions of exposure.
  • the yellow and magenta side densities measured behind color filters after processing are constant and independent of the conditions of exposure.
  • the azo masking couplers mentioned above may either be emulsified in the photographic layers or introduced in the form of aqueous alkaline solutions. It is frequently observed that the coupling activity of hydrophobic emulsified couplers is less than that of hydrophilic couplers dissolved in an aqueous alkaline solvent. If, however, attempts are made to render such couplers envisaged for the emulsification process more hydrophilic by introducing suitable substituents, difficulties arise in the emulsification process. This causes the choice of substituents to be severely restricted. The choice is still further reduced by the necessity of keeping the dyes used within a suitable absorption range for masking the cyan side densities.
  • red azo masking couplers which are sufficiently hydrophobic to ensure that they can be efficiently emulsified but are sufficiently hydrophilic to enable the coupling reaction in the layer to take place sufficiently rapidly; furthermore, the absorption maximum should be situated so that the side densities of the cyan partial image are masked as completely as possible.
  • a Rf, R or R represent hydrogen or alkyl with up to 18 carbon atoms, these groups being either the same or different, at least one of these groups being an alkyl radical with preferably 12 to 18 carbon atoms which renders the compound resistant to diffusion;
  • R represents alkyl with four to seven carbon atoms, or cycloalkyl such as cyclohexyl which may contain other substituents, e.g. alkyl preferably with up to five carbon atoms, especially methyl.
  • reaction mixture is adjusted to pH 7 with glacial acetic acid and the slimy precipitate formed is taken up in methylene chloride which is then dried with sodium sulfate and the residue is concentrated by evaporation.
  • the product is purified by recrystallizing from ethyl acetate.
  • the new red azo masking couplers are superior to the corresponding known couplers in many of their properties. They are red to magenta in color, having an absorption maximum between 450 and 510 nm. This absorption range satisfies the requirement that both the blue and the green absorption range of the cyan coupling dyes formed should be effectively masked.
  • Another advantage of the couplers is that due to the combination of esters of aliphatic alcohols which have a medium number of carbon atoms with a sulfonamide group in the'same molecule the couplers are especially advantageous in three of their properties: Suitable absorption of dyes, efficient emulsifiability and excellent reactivity.
  • the masking couplers to be used according to the invention may be used either alone of preferably together with colorless cyan couplers in color photographic silver halide emulsions, especially in'layers which are sensitized to red light.
  • the masking couplers are preferably incorporated in an emulsified form with the silver halide emulsion.
  • the compound is dissolved in known manner in suitable organic solvents, e.g. in esters of aliphatic carboxylic acids, especially in ethyl acetate, and this solution a is emulsified in the silver halide emulsion which is ready for casting.
  • suitable organic solvents e.g. in esters of aliphatic carboxylic acids, especially in ethyl acetate
  • crystalloids that is to say high boiling solvents, e.g. tricresyl phosphate or dibutylphthalate
  • the new substances are used together with colorless cyan couplers, the substances may be added to the light sensitive silver halide emulsions either successively or together from a common solution.
  • the method of addition to the emulsion is not critical. and the most suitable method can easily be determined by simple tests.
  • the required dye emulsions may be prepared, for example, as follows:
  • a fatty alcohol sulfonate per 100 g of gelatin solution is added as emulsifier to a 7.5 percent solution of a photographic gelatin.
  • the required quantity of dye is then dissolved in 3 to 5 times its quantity of ethyl acetate and this solution is run into a gelatin solution heated to 50 C, using a Kotthoff stirrer.
  • the emulsification time is 5 to 15 minutes, depending on the quantity. Any ethyl acetate still present is removed under vacuum.
  • the emulsion is then ready for use. If necessary, 10 to 100 percent of an oil forming substance such as dibutylphthalate, the amount being preferably based on the quantity of dye per kg:
  • the light sensitive emulsions may contain silver chloride, silver bromide or mixtures thereof, or with a small iodide content of up to mols percent.
  • the binders used may be the usual hydrophilic binders such as proteins, especially gelatin, polyvinyl alcohol, polyvinyl pyrrolidone, cellulose derivatives such as carboxymethylcellulose or derivatives of alginic acid.
  • the emulsions may also contain the usual derivatives, e.g. optical or chemical sensitizers, stabilizers, hardeners, and plasticizers.
  • Any color forming developers which contain a primary amino group may be used for development. It is preferred to use those of the paraphenylenediamine series, e.g. N,N-diethyl-para-phenylenediamine, 2- amino-5-diethylaminotoluene-N-butyl-N-w-sulfobutylparaphenylenediamine, 2-amino-5-(N-ethyl-N-B- methanesulfonamidoethylamino)toluene, and 2- amino-S-N-ethyl-N-hydroxyethylaminotoluene.
  • paraphenylenediamine series e.g. N,N-diethyl-para-phenylenediamine, 2- amino-5-diethylaminotoluene-N-butyl-N-w-sulfobutylparaphenylenediamine, 2-amino-5-(N-ethy
  • EXAMPLE 1 3.2 g of the red masking coupler 6 in that table of formulae are dissolved in ml of ethyl acetate and then emulsified in 250 g of a 7.5 percent gelatin solution.
  • the emulsion is mixed with 100 g of silver bromide gelatin emulsion (50 g of silver in the form of silver halide per kg) with stirring and diluted with 1 200 ml of water.
  • To this emulsion mixture are added 15 ml of a 10 percent aqueous saponin solution and 5 ml of a 0.5 percent aqueous chrome acetate solution and the emulsion is then cast on. a layer support of cellulose triacetate. Thickness of layer 5 After drying, the film is exposed behind a grey step wedge and developed for 6 minutes in a developer of the following composition:
  • EXAMPLE 2 2.5 g of the cyan coupler of the following formula are added in the form of a gelatin dispersion together with 0.25 g of dibutylphthalate, as oil forming agent, to 100 g of a red-sensitized silver bromide gelatin emulsion which contains 70 g of silver in the form of silver halide aiin 1.7 g of masking coupler 3, also dispersed in gelatin, are then added.
  • R R and R represents alkyl and one of R R or R,-, is an alkyl radical with 12 to l8 carbon atoms.
  • a material as claimed in claim 3 in which 10 to percent, based on the quantity of dye used, of dibutylphthalate is added to the dye solution before emulsification.
  • a material as claimed in claim 1 containing in the silver halide emulsion layer in addition colorless cyan coupler selected from the group consisting of cyan couplers of the phenol or naphthol series.

Abstract

A light sensitive color photographic material having at least one silver halide emulsion layer which contains a red azo masking coupler of the following formula: WHEREIN R1, R2, R3 and R4 are as defined in the description, which red cyan coupler has advantageous properties with respect to suitable absorption dyes, efficient emulsifiability and excellent reactivity.

Description

United States Patent Puschel et al.
[ Oct. 29, 1974 1 SILVER HALIDE PHOTOGRAPHIC MATERIAL CONTAINING AZO MASKING COUPLERS [75] Inventors: Walter Puschel, Leverkusen,
Germany; Gaston Jacob Benoy, Edegem, Belgium; Dietmar Kalz, Koeln, Germany [73] Assignee: Agta-Gevaert Aktiengesellschaft,
Leverkusen, Germany [22] Filed: May 4, 1972 21 Appl. No.: 250,300
[30] Foreign Application Priority Data May 7, 1971 Germany 2122570 [52] US. Cl. 96/100, 96/9 [51] Int. Cl G03c 1/40 [58] Field of Search 96/100, 9, 56.1
[56] References Cited UNITED STATES PATENTS 3,459,552 8/1969 Yoshida et al. 96/100 3,556,796 l/1971 Eynde et al 96/9 3,615,225 10/1971 Otto et al 96/100 3,676,142 7/1972 Carpentier et al 96/9 Primary Examiner-J. Travis Brown Attorney, Agent, or Firm-Connolly and Hultz [5 7 ABSTRACT A light sensitive color photographic material having at least one silver halide emulsion layer which contains a red 2120 masking coupler of the following formula:
OH S OzNH-Rl wherein R R R and R are as defined in the description, which red cyan coupler has advantageous properties with respect to suitable absorption dyes, efficient emulsifiability and excellent reactivity.
5 Claims, No Drawings SILVER IIALIDE PIIOTOGRAPHIC MATERIAL CONTAINING AZO MASKING COUPLERS The invention relates to a color photographic material with improved color reproduction which contains red cyan couplers for the production of so-called builtin masks, preferably in an emulsified form.
It is known that the unwanted side color densities of the image dyes produced by chromogenic development of multilayered color photographic materials can be eliminated by masking processes. This may be achieved by using so-called built-in masks in color photographic materials. These masks may be produced, for example, in the course of the photographic process, by using socalled masking couplers which have a color which masks the unwanted side color densities of the image dyes. Color couplers suitable for this purpose generally have the same chemical structure as ordinary color couplers but at the point of coupling for the reaction with the oxidized color developer they contain a group, generally an azo dye group, which imparts to the color coupler the color which is split off in the reaction with the oxidized color developer. In the process of color development, the image dye is formed in the exposed and developed areas while in the unexposed areas the color of the colored coupler used is preserved. Ideally, the gradation of unwanted side densities obtained in the course of processing is compensated by an equal but opposite gradation of the masking dye so that the density in the unwanted region of the spectrum is uniform regardless of the conditions of exposure. In an efficiently masked cyan coupler, for example, the yellow and magenta side densities measured behind color filters after processing are constant and independent of the conditions of exposure.
The azo masking couplers mentioned above may either be emulsified in the photographic layers or introduced in the form of aqueous alkaline solutions. It is frequently observed that the coupling activity of hydrophobic emulsified couplers is less than that of hydrophilic couplers dissolved in an aqueous alkaline solvent. If, however, attempts are made to render such couplers envisaged for the emulsification process more hydrophilic by introducing suitable substituents, difficulties arise in the emulsification process. This causes the choice of substituents to be severely restricted. The choice is still further reduced by the necessity of keeping the dyes used within a suitable absorption range for masking the cyan side densities.
It is an object of the invention to find red azo masking couplers which are sufficiently hydrophobic to ensure that they can be efficiently emulsified but are sufficiently hydrophilic to enable the coupling reaction in the layer to take place sufficiently rapidly; furthermore, the absorption maximum should be situated so that the side densities of the cyan partial image are masked as completely as possible.
It now has been found a light sensitive color photographic material having at least one silver halide emulsion layer which contains a red cyan coupler of the following formula:
wherein A Rf, R or R represent hydrogen or alkyl with up to 18 carbon atoms, these groups being either the same or different, at least one of these groups being an alkyl radical with preferably 12 to 18 carbon atoms which renders the compound resistant to diffusion;
R represents alkyl with four to seven carbon atoms, or cycloalkyl such as cyclohexyl which may contain other substituents, e.g. alkyl preferably with up to five carbon atoms, especially methyl.
The following compounds have proved to be especially suitable:
(1) (|)H I SOz-NHCH o ONH -OHa liaHu N ii N l -0 (2) I s OH S O:|'NHCH3 C O NH III-CH3 l CraHar N ll N H/ CH3 (3) S Qz-NH-CrsHflr @woo -oiun Compound 4 is a mixture of isomers. The compounds according to the invention are prepared according to methods known in the literature by diazotising the corresponding amines and coupling with naphthol carboxylic acid anilide s. Compound 5 of the table of formulae, for example is prepared as follows:
2.9 g of anthranilic acid cyclohexyl ester are dissolved in 4 ml of cone. hydrochloric acid and ml of water with heating, then'cooled to 0 C and diazotised by the addition of a solution of 0.85 g of sodium nitrite in 3 ml of water. The reaction mixture is then stirred for 1 hour, the excess of nitrite is destroyed and the pH is adjusted to 6-7. The product is then coupled with 6 g of the corresponding coupling component dissolved in l0 ml of pyridine with the addition of ml of water and 2 ml of cone. sodium hydroxide solution. The pH should be maintained at about 12 during the coupling reaction. After 15 minutes, the reaction mixture is adjusted to pH 7 with glacial acetic acid and the slimy precipitate formed is taken up in methylene chloride which is then dried with sodium sulfate and the residue is concentrated by evaporation. The product is purified by recrystallizing from ethyl acetate.
The new red azo masking couplers are superior to the corresponding known couplers in many of their properties. They are red to magenta in color, having an absorption maximum between 450 and 510 nm. This absorption range satisfies the requirement that both the blue and the green absorption range of the cyan coupling dyes formed should be effectively masked. Another advantage of the couplers is that due to the combination of esters of aliphatic alcohols which have a medium number of carbon atoms with a sulfonamide group in the'same molecule the couplers are especially advantageous in three of their properties: Suitable absorption of dyes, efficient emulsifiability and excellent reactivity.
The masking couplers to be used according to the invention may be used either alone of preferably together with colorless cyan couplers in color photographic silver halide emulsions, especially in'layers which are sensitized to red light.
The masking couplers are preferably incorporated in an emulsified form with the silver halide emulsion.
The compound is dissolved in known manner in suitable organic solvents, e.g. in esters of aliphatic carboxylic acids, especially in ethyl acetate, and this solution a is emulsified in the silver halide emulsion which is ready for casting. According to another method of carrying out this process, so-called crystalloids, that is to say high boiling solvents, e.g. tricresyl phosphate or dibutylphthalate, may be added to the coupler. If the new substances are used together with colorless cyan couplers, the substances may be added to the light sensitive silver halide emulsions either successively or together from a common solution. The method of addition to the emulsion is not critical. and the most suitable method can easily be determined by simple tests.
The required dye emulsions may be prepared, for example, as follows:
0.25 g of a fatty alcohol sulfonate per 100 g of gelatin solution is added as emulsifier to a 7.5 percent solution of a photographic gelatin.
The required quantity of dye is then dissolved in 3 to 5 times its quantity of ethyl acetate and this solution is run into a gelatin solution heated to 50 C, using a Kotthoff stirrer. The emulsification time is 5 to 15 minutes, depending on the quantity. Any ethyl acetate still present is removed under vacuum. The emulsion is then ready for use. If necessary, 10 to 100 percent of an oil forming substance such as dibutylphthalate, the amount being preferably based on the quantity of dye per kg:
used, may be added to the dye solution before emulsification.
The light sensitive emulsions may contain silver chloride, silver bromide or mixtures thereof, or with a small iodide content of up to mols percent. The binders used may be the usual hydrophilic binders such as proteins, especially gelatin, polyvinyl alcohol, polyvinyl pyrrolidone, cellulose derivatives such as carboxymethylcellulose or derivatives of alginic acid.
The emulsions may also contain the usual derivatives, e.g. optical or chemical sensitizers, stabilizers, hardeners, and plasticizers.
Any color forming developers which contain a primary amino group may be used for development. It is preferred to use those of the paraphenylenediamine series, e.g. N,N-diethyl-para-phenylenediamine, 2- amino-5-diethylaminotoluene-N-butyl-N-w-sulfobutylparaphenylenediamine, 2-amino-5-(N-ethyl-N-B- methanesulfonamidoethylamino)toluene, and 2- amino-S-N-ethyl-N-hydroxyethylaminotoluene.
The following Examples illustrate the invention:
EXAMPLE 1 3.2 g of the red masking coupler 6 in that table of formulae are dissolved in ml of ethyl acetate and then emulsified in 250 g of a 7.5 percent gelatin solution. The emulsion is mixed with 100 g of silver bromide gelatin emulsion (50 g of silver in the form of silver halide per kg) with stirring and diluted with 1 200 ml of water. To this emulsion mixture are added 15 ml of a 10 percent aqueous saponin solution and 5 ml of a 0.5 percent aqueous chrome acetate solution and the emulsion is then cast on. a layer support of cellulose triacetate. Thickness of layer 5 After drying, the film is exposed behind a grey step wedge and developed for 6 minutes in a developer of the following composition:
2.5 g of N.N-diethyl-p-phenylenediamine sulphate 2 g of sodium sulfite l g of potassium bromide 25 g of potassium carbonate 0.5 g of hydroxylamine sulfate Water up to 1 litre.
After bleaching and fixing in the usual baths, a cyan colour wedge with very efficiently masked yellow and red side densities is obtained.
EXAMPLE 2 2.5 g of the cyan coupler of the following formula are added in the form of a gelatin dispersion together with 0.25 g of dibutylphthalate, as oil forming agent, to 100 g of a red-sensitized silver bromide gelatin emulsion which contains 70 g of silver in the form of silver halide aiin 1.7 g of masking coupler 3, also dispersed in gelatin, are then added.
15 ml of a 10 percent aqueous saponin solution and 5 ml of a 0.5 percent aqueous chrome acetate solution are then added to this emulsion mixture and the mixture is cast on 10 m of a layer support of cellulose triacetate. The thickness of the layer is 4 pm.
After drying, the material is exposed behind a grey step wedge and developed in a developer of the following composition:
5 g of 2-amino-5-(N-ethyl-N-B-methane sulfonamidoethylamino)-toluene 4 ml of benzyl alcohol 2.5 g of sodium hexametaphosphate 2.0 g of sodium sulfite sicc.
1.0 g of sodium bromide 0.5 g of sodium hydroxide 50 g of Na2CO3.H O
Water up to l litre.
After carrying out the other usual color photographic processes involving bleaching and fixing, a cyan colour is obtained in which the yellow and the magenta side densities of the cyan dye formed is efficiently masked. The masking effect is considerably better than that obtained with known red cyan couplers. Similar results are obtained when using a silver iodobromide emulsion which contains g of silver in the form of silver halide and which contains, for every g of emulsion, l g of theabove mentioned cyan coupler and 0.65 g of masking coupler 3, also in an emulsified form.
The excellent effect of the masking couplers used according to the invention is also manifested when using other cyan couplers in combination with, these masking couplers. Thus, for example equally good results are obtained in the silver halide emulsion mentioned above when the cyan coupler is replaced by couplers of the following formulae:
R 300ml (CH1) 4-0 s'daiiiit'i" V O 0 UPI-O R4 in which R,, R or R represents hydrogen or alkyl with upto 18 carbon atoms, these groups being either the same or different, at least one of these groups being an alkyl radical which renders the compound resistant to diffusion and represents alkyl having four to seven carbon atoms or cycloalkyl.
2. A material as claimed in claim 1 in which R R and R represents alkyl and one of R R or R,-, is an alkyl radical with 12 to l8 carbon atoms.
3. A material as claimed in claim I in which the red cyan couplers are incorporated in the silver halide emulsion layer in an emulsified form.
4. A material as claimed in claim 3 in which 10 to percent, based on the quantity of dye used, of dibutylphthalate is added to the dye solution before emulsification.
5. A material as claimed in claim 1 containing in the silver halide emulsion layer in addition colorless cyan coupler selected from the group consisting of cyan couplers of the phenol or naphthol series.
73,713" UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTIQ Patent No. 5 Dated O tober 2Q, 1071;
Inventor(s) Walter SChel eta1 It is certified that error appears in the above-identified patent. and. that said Letters Patent arevhereby corrected as shown below:
Column 8, claim l, line iz i'sfert R before "represents".
Signed and [sealed this 18th day of March 1975.
- (SEAL) Attest:
c. MARSHALL DANN- -RUTH C. MASON v Commissioner of Patents Attesting Officer and Trademarks

Claims (5)

1. A LIGHT SENSITIVE COLOR PHOTOGRAPHIC MATERIAL HAVING AT LEAST ONE SILVER HALIDE EMULSION LAYER WHICH CONTAINS A RED CYAN COUPLER, WHICH CYAN COUPLER IS OF THE FOLLOWING GENERAL FORMULA:
2. A material as claimed in claim 1 in which R1, R2 and R3 represents alkyl and one of R1, R2 or R3 is an alkyl radical with 12 to 18 carbon atoms.
3. A material as claimed in claim 1 in which the red cyan couplers are incorporated in the silver halide emulsion layer in an emulsified form.
4. A material as claimed in claim 3 in which 10 to 100 percent, based on the quantity of dye used, of dibutylphthalate is added to the dye solution before emulsification.
5. A material as claimed in claim 1 containing in the silver halide emulsion layer in addition colorless cyan coupler selected from the group consisting of cyan couplers of the phenol or naphthol series.
US00250300A 1971-05-07 1972-05-04 Silver halide photographic material containing azo masking couplers Expired - Lifetime US3844795A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4141730A (en) * 1975-04-08 1979-02-27 Fuji Photo Film Co., Ltd. Multilayer color photographic materials
US4250251A (en) * 1978-07-27 1981-02-10 Eastman Kodak Company Phenylsulfamoyl couplers, coupler compositions and photographic elements suited to forming integral sound tracks
US4250252A (en) * 1974-10-09 1981-02-10 Agfa-Gevaert, A.G. Light-sensitive color photographic material

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5533439A (en) * 1978-08-31 1980-03-08 Konishiroku Photo Ind Co Ltd 2-sulfamoyl-5-sulfamido-1-naphthol

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3459552A (en) * 1965-02-03 1969-08-05 Fuji Photo Film Co Ltd Silver halide emulsions containing magenta-colored cyan couplers
US3556796A (en) * 1965-10-13 1971-01-19 Agfa Gevaert Nv Silver halide emulsion containing naphthol colour couplers for cyan
US3615225A (en) * 1967-12-21 1971-10-26 Agfa Gevaert Ag Color photographic material
US3676142A (en) * 1968-09-10 1972-07-11 Agfa Gevaert Method of incorporating photographic ingredients into photographic colloid compositions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1522423A1 (en) * 1967-01-28 1969-07-31 Agfa Gevaert Ag Improved color photographic material

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3459552A (en) * 1965-02-03 1969-08-05 Fuji Photo Film Co Ltd Silver halide emulsions containing magenta-colored cyan couplers
US3556796A (en) * 1965-10-13 1971-01-19 Agfa Gevaert Nv Silver halide emulsion containing naphthol colour couplers for cyan
US3615225A (en) * 1967-12-21 1971-10-26 Agfa Gevaert Ag Color photographic material
US3676142A (en) * 1968-09-10 1972-07-11 Agfa Gevaert Method of incorporating photographic ingredients into photographic colloid compositions

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4250252A (en) * 1974-10-09 1981-02-10 Agfa-Gevaert, A.G. Light-sensitive color photographic material
US4141730A (en) * 1975-04-08 1979-02-27 Fuji Photo Film Co., Ltd. Multilayer color photographic materials
US4250251A (en) * 1978-07-27 1981-02-10 Eastman Kodak Company Phenylsulfamoyl couplers, coupler compositions and photographic elements suited to forming integral sound tracks

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FR2137576B1 (en) 1977-08-26
DE2122570A1 (en) 1972-11-23
DE2122570C3 (en) 1980-08-28
IT958571B (en) 1973-10-30
CA998281A (en) 1976-10-12

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