WO1993023792A1 - Melanges aqueux de colorants de sensibilisation spectrale pour emulsions photographiques - Google Patents

Melanges aqueux de colorants de sensibilisation spectrale pour emulsions photographiques Download PDF

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Publication number
WO1993023792A1
WO1993023792A1 PCT/US1992/004024 US9204024W WO9323792A1 WO 1993023792 A1 WO1993023792 A1 WO 1993023792A1 US 9204024 W US9204024 W US 9204024W WO 9323792 A1 WO9323792 A1 WO 9323792A1
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WO
WIPO (PCT)
Prior art keywords
dye
water
independently represents
substituted
substitute sheet
Prior art date
Application number
PCT/US1992/004024
Other languages
English (en)
Inventor
John William Boettcher
Kim Georgette Kvocka
Original Assignee
Eastman Kodak Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eastman Kodak Company filed Critical Eastman Kodak Company
Priority to PCT/US1992/004024 priority Critical patent/WO1993023792A1/fr
Priority to JP51200093A priority patent/JP3309979B2/ja
Priority to DE69227322T priority patent/DE69227322T2/de
Priority to EP92912683A priority patent/EP0640225B1/fr
Publication of WO1993023792A1 publication Critical patent/WO1993023792A1/fr

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Classifications

    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes
    • G03C1/14—Methine and polymethine dyes with an odd number of CH groups
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein

Definitions

  • This invention relates to a process for
  • Dyes for spectrally sensitizing silver halide emulsions are known to be substantially insoluble in water for all practical purposes. Accordingly, such dyes, as well as other photographic additives which are capable of being adsorbed on the grain surfaces of silver salts, have been added to photographic silver halide emulsions in the form of solutions in suitable water miscible solvents such as methyl alcohol,
  • emulsion which in turn causes a reduced stability during processing including phase separation between hydrophilic and hydrophobic phases, agglomeration, and coalescence as well as flocculation before casting.
  • Additives which need not be held on the surface of silver halide crystals by adsorption after their introduction into a photographic emulsion have long been incorporated into silver halide emulsions in the form of dispersions.
  • the additive is usually dissolved in a suitable solvent, which is generally immiscible with water, in the presence of an oil former and wetting agent, and then emulsified into an aqueous gelatin solution.
  • a suitable solvent which is generally immiscible with water
  • One method for obviating the harmful effects of using water miscible or immiscible organic solvents to incorporate substantially insoluble additives into silver halide emulsions and dispersions as described in British Patent 1,570,362 is to sand mill such additives in water to a particle size of less than 1 micron in the presence of a surfactant which gives rise to a surface tension of not less than 38 dynes/cm in water when used in a
  • a process for preparing concentrated sensitizing dye-water compositions for the sensitization of photographic emulsions which is devoid of the
  • a sensitizing dye having a solubility in water as low as about 0.005 weight percent to water or a water-polymer medium with agitation at a temperature ranging from about 20° to about 50° C and continuing agitation for from about 30 minutes to about 5 hours.
  • the process of the invention is simple, versatile and forgiving. It does not require the use of solvents, surfactants, milling of the dye to very fine starting grain sizes, use of highly elevated
  • the concentration of dye employed in the process generally exceeds that amount of dye which is soluble in the dispersion medium at the preparation, usage, or storage temperatures.
  • amounts ranging from about 0.5 to about 5 weight percent of dye based on the total weight of the mixture are employed.
  • Cyanine dyes which have a solubility of at least about 0.005% by weight in water are preferably used in the process of the invention.
  • Preferred dyes have the formula :
  • Z 1 and Z 2 each independently represents the atoms necessary to complete a substituted or unsubstituted heterocyclic nucleus, each L independently represents a substituted or unsubstituted methine group, n is a positive integer of from 1 to 4, p and q each
  • a and A' each, independently represents a divalent alkyl or substituted alkyl linking group.
  • Q 1 , Q 2 , Q 3 and Q 4 each independently represents halogen, alkyl, alkoxy or may contain the atoms necessary to form a beta or linear naphtho-fused ring; R 1 and R 2 each independently represent a sulfoalkyl or substituted sulfoalkyl group; and X + is a cation such as sodium, hydrogen, triethylammonium or ethyl pyridinium.
  • the process of the invention provides concentrated sensitizing dye-water compositions that are homogeneous, solvent-free and dispersant- free , such compositions are nevertheless resistant to settling. If some settling does occur, slight agitation or mixing renders the composition homogeneous once again.
  • a solid sensitizing dye powder that is somewhat soluble in water is mixed into an "aqueous medium", which term includes a polymer-containing aqueous medium (water-polymer medium), preferably containing gelatin, at a concentration of dye greater than that which will dissolve in the medium at the temperature, pressure, or other conditions of processing, storage, or use of the composition. Amounts ranging from about 0.5 to about 5 weight percent based on the total weight of the components of the composition are preferred. Because the process can be carried out in the absence of either solvent or surfactant, it is simpler, faster, more forgiving, and more flexible than prior processes.
  • the medium to which the dye is added is heated to a preparation temperature ranging from about 20° to about 50° C and maintained at that
  • temperatures can be used with other polymers.
  • the process is also flexible in that one temperature can be used during addition while a different temperature is used during mixing.
  • composition can be mixed or agitated by any suitable means using any suitable device including magnetically driven stirring bars of various shapes and motor driven shaft stirrers of the propellor or Cowles type.
  • a formula provided by J. Y. Oldshue in "Fluid Mixing Technology", McGraw-Hill, New York, 1983, p. 83, can be used to calculate the preferred amount of
  • undispersed dye particles can be obtained when p/kg > 50 ⁇ 10 9 .
  • the process of the invention can be employed using spectrally sensitizing dyes, particularly
  • cyanine dyes having a solubility as low as about 0.005% by weight of the dye in water despite the absence of solvents, dispersants, surfactants or wetting agents.
  • Preferred dyes have the formula
  • Z 1 and Z 2 each independently represents the atoms necessary to complete a substituted or unsubstituted heterocyclic nucleus, each L independently represents a substituted or unsubstituted methine group, n is a positive integer of from 1 to 4, p and q each
  • a and A' each independently represents a divalent alkyl or substituted alkyl linking group.
  • n is 0 or 1;
  • X 1 and X 2 each independently represents oxygen or sulfur;
  • Q 1 , Q 2 , Q 3 and Q 4 each independently represents halogen, alkyl, alkoxy or may contain the atoms necessary to form a beta or linear naphtho-fused ring;
  • R 1 and R 2 each independently represent a sulfoalkyl or substituted sulfoalkyl group;
  • X + is a cation such as sodium, hydrogen, triethylammonium or ethyl pyridinium.
  • the solvent-free, dispersant-free, dye-water compositions prepared by the process of the invention and containing from about 0.5 to about 5 weight percent of the dyes defined herein are resistant to settling.
  • Concentrated sensitizing dye-water compositions of the invention for the spectral sensitization of photographic emulsions can be prepared by any suitable method.
  • the concentrated dye-water compositions are preferably prepared by first mixing gelatin with water and then heating to prepare an initial gelatin solution.
  • the gel solution is heated and stirred or mixed or otherwise agitated while a sensitizing dye of the invention is introduced, preferably in the form of a powder slowly and uniformly over the surface of the mixture being stirred.
  • stirring is continued for a period of time, generally ranging from about 30 minutes to about 5 hours or longer as desired, to produce the concentrated dye-water
  • a dispersion of a salt of a sensitizing dye of the invention is prepared in a 24.75 cm high stainless steel can having a diameter of about 20 cm into which was introduced about 300 g of dry,
  • the blade of the stirrer is then lowered to about 5 cm from the bottom of the can and the rpms are increased to about 660. Stirring is continued for about one hour.
  • the final dye dispersion contains about 0.5% by weight of dye and about 6% by weight of gelatin based on the weight of the entire dispersion.
  • the dye compositions of the invention can also contain a polymeric binder or protective colloid which can be used in the photographic emulsion layers of intermediate layers of a photographic light-sensitive material.
  • Gelatin is advantageously used although other hydrophilic colloids can be used alone or together with gelatin. Either lime processed or acid processed, deionized gelatin can be used.
  • Any suitable silver halide such as silver bromide, silver iodobromide, silver chlorobromide, silver chloride and the like can be used in the photographic emulsion layer of the photographic light-sensitive material sensitized in accordance with the invention.
  • the photographic emulsion can be prepared by any suitable method including an acid process, a neutral process, an ammonia process or the like using a
  • Silver halide emulsions are usually chemically sensitized, for example by sulfur sensitization using active gelatin or compounds such as thiosulfates, thioureas, mercapto compounds and rhodanines containing sulfur capable of reacting with silver; a reduction sensitization process using reducing substances such as stannous salts, amines, hydrazine derivatives,
  • the photographic emulsion can include various compounds for preventing fog formation or stabilizing photographic characteristics during production, storage, or processing.
  • antifoggants or stabilizers include azoles such as benzothiazolium salts,
  • nitroimidazoles nitrobenzimidazoles, chlorobenzimid-azoles, bromobenzimidazoles, mercapto-thiazoles,
  • mercaptothiadiazoles aminotriazoles, benzotriazoles, nitrobenzotriazoles, mercaptotetrazoles particularly 1-phenyl-5-mercaptotetrazole; mercaptopyrimidines,
  • oxazolinethione azaindenes such as triazanidenes, tetraazaindenes particularly 4-hydroxy substituted
  • Various surface active agents can be incorporated into the photographic emulsion or other hydrophilic colloid layers of the photographic light-sensitive materials sensitized in accordance with the invention as coating aids, to prevent charging, improve slip properties, accelerate emulsification and
  • the photographic emulsion layer can also contain compounds such as polyalkylene oxide or its ether, ester, amine or the like derivatives, thioether compounds, thiomorpholines, quaternary ammonium salt compounds, urethane derivatives, urea derivatives, imidazole derivatives, and 3-pyrazolidones to increase sensitivity or contrast or accelerate development.
  • compounds such as polyalkylene oxide or its ether, ester, amine or the like derivatives, thioether compounds, thiomorpholines, quaternary ammonium salt compounds, urethane derivatives, urea derivatives, imidazole derivatives, and 3-pyrazolidones to increase sensitivity or contrast or accelerate development.
  • Water insoluble or only sparingly soluble synthetic polymer dispersions can be incorporated into the photographic emulsion layer or other hydrophilic colloid layer to improve dimensional stability and the like.
  • Some synthetic polymers which can be used include homo or copolymers of alkyl acrylate or methacrylate, alkoxyalkyl acrylate or methacrylate, glycidyl acrylate or methacrylate, acrylamide or methacrylamide, vinyl esters such as vinyl acetate, acrylonitrile, olefins, styrene and the like and copolymers thereof with acrylic acid, methacrylic acid, alpha, beta-unsaturated
  • dicarboxylic acid hydroxyalkyl acrylate or methacrylate, sulfoalkyl acrylate or methacrylate, styrenesulfonic acid and the like.
  • sensitizing dyes which do not in themselves give rise to spectral sensitization but provide a supersensitizing effect such as, for example, aminostyryl compounds substituted with a nitrogen-containing heterocyclic group including those described in U.S. Patents 2,933,390 and 3,635,721 which are hereby incorporated herein by reference, aromatic organic acid-formaldehyde condensates such as those described in U.S. Patent 3,743,510 which is hereby incorporated herein by reference, cadmium salts, azaindene compounds and the like.
  • the concentrated dye-water sensitizing compositions of the invention can be used in multilayer multicolor photographic materials containing layers sensitive to at least two different spectral wavelength ranges on a support.
  • photographic material generally possesses at least one red-sensitive silver halide emulsion layer, at least one green-sensitive silver halide emulsion layer, and at least one blue-sensitive silver halide emulsion layer on a support.
  • the order of the layers can be varied as desired.
  • a cyan forming coupler is present in the red-sensitive emulsion layer
  • a magenta forming coupler is present in the green-sensitive emulsion layer
  • a yellow forming coupler is present in the blue-sensitive emulsion layer, respectively. Different combinations can be employed as desired.
  • Any suitable dye-forming couplers that is, compounds capable of forming color upon oxidative
  • aromatic primary amine developing agents such as phenylene-diamine derivatives, aminophenol derivatives and the like during color development
  • magenta couplers such as 5- pyrazolone coupler
  • cyanoacetylcoumarone couplers and open chain acylaceto-nitrile couplers, and the like yellow couplers such as acylacetamide couplers including benzoylacetanilides, pivalpoylacetanilides and the like; cyan couplers such as naphthol couplers and phenol couplers and the like.
  • hydrophobic group or ballast group within the molecule or polymeric coupler is used. They may be either 4-equivalent or 2-equivalent with respect to silver ions. Colored couplers capable of exerting color correction effects or couplers capable of releasing development inhibitors during the course of development or DIR couplers, can also be used. Two or more couplers can be employed.
  • the photographic material can contain inorganic or organic hardeners in the emulsion layer or other hydrophilic colloid layer thereof.
  • inorganic or organic hardeners such as chromium alum, chromium acetate and the like; aldehydes such as formaldehyde, glyoxal,
  • N-methylol compounds such as dimethylolurea, methyloldimethyl-hydantoin and the like; dioxane derivatives such as 2,3-dihydroxydioxane and the like; active vinyl compounds such as 1,3,5-triacryloylhexahydro-s-triazine and the like;
  • mucohalogenic acids such as mucochloric acid
  • mucophenoxy-chloric acid and the like can be used, either alone or in combination.
  • the photographic light-sensitive material can also contain hydroquinone derivatives, aminophenol
  • hydrophilic colloid layers of a photographic lighr sensitive material of the invention include benzotriazole compounds substituted with aryl groups, and 4-thiazolidone, benzophenone, cinnamic acid ester,
  • Ultraviolet light absorbing couplers such as alpha naphthol type cyan dye forming couplers and ultraviolet light absorbing polymers can also be used.
  • ultraviolet light absorbing agents can also be mordanted in a specific layer, if desired.
  • Photographic light sensitive elements prepared using the spectrally sensitized emulsions of the
  • invention may contain water soluble dyes in the
  • hydrophilic colloid layers as a filter dye or for other purposes such as irradiation prevention and the like.
  • suitable dyes include oxonol, hemioxonol, styryl, merocyanine, cyanine, azo and the like dyes.
  • Oxonol, hemioxonal, and merocyanine dyes are particularly useful.
  • color fading prevention agents can also be used as well as color image stabilizers, either alone or in combination with each other.
  • suitable color fading prevention agents include hydroquinone derivatives, gallic acid derivatives, p-oxyphenol
  • Silver halide photographic emulsions sensitized in accordance with the invention can also contain various other additives used for photography including any suitable hardeners, surfactants, fluorescent whiteners, physical property modifiers such as humectants, water dispersants and the like; condensates of phenols and formalin and the like.
  • Silver halide emulsions sensitized in accordance with the invention can be coated on any suitable support and dried to prepare a light sensitive silver halide photographic element.
  • suitable supports include paper, glass, cellulose acetate, cellulose nitrate, polyester, polyamide, polystyrene and the like or laminated products of two or more substrates such as laminated products of paper and a polyolefin such as polyethylene, polypropylene and the like.
  • the support may be subjected to various surface modification
  • photographic emulsion on the support may be carried out conventionally by dip coating, roller coating, multislide hopper coating, curtain flow coating and the like
  • each light sensitive emulsion layer can comprise two emulsion layers with different

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)

Abstract

L'invention se rapporte à un procédé de préparation de compositions à base d'eau et de colorant concentré pour des émulsions photographiques de sensibilisation spectrale en l'absence d'un solvant ou d'un tensioactif, et qui consiste à ajouter un colorant de sensibilisation présentant une solubilité dans l'eau abaissée jusqu'à environ 0,005 pour cent en poids par rapport à de l'eau ou à un milieu d'eau-polymère, avec un brassage à une température d'environ 20° à environ 50 °C et un brassage continu pendant environ 30 minutes à environ 5 heures.
PCT/US1992/004024 1992-05-14 1992-05-14 Melanges aqueux de colorants de sensibilisation spectrale pour emulsions photographiques WO1993023792A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
PCT/US1992/004024 WO1993023792A1 (fr) 1992-05-14 1992-05-14 Melanges aqueux de colorants de sensibilisation spectrale pour emulsions photographiques
JP51200093A JP3309979B2 (ja) 1992-05-14 1992-05-14 写真乳剤用分光増感色素の水性混合物
DE69227322T DE69227322T2 (de) 1992-05-14 1992-05-14 Wässrige farbstoffsuspensionen zur spektralen sensibilisierung photographischer emulsionen
EP92912683A EP0640225B1 (fr) 1992-05-14 1992-05-14 Melanges aqueux de colorants de sensibilisation spectrale pour emulsions photographiques

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1992/004024 WO1993023792A1 (fr) 1992-05-14 1992-05-14 Melanges aqueux de colorants de sensibilisation spectrale pour emulsions photographiques

Publications (1)

Publication Number Publication Date
WO1993023792A1 true WO1993023792A1 (fr) 1993-11-25

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PCT/US1992/004024 WO1993023792A1 (fr) 1992-05-14 1992-05-14 Melanges aqueux de colorants de sensibilisation spectrale pour emulsions photographiques

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EP (1) EP0640225B1 (fr)
JP (1) JP3309979B2 (fr)
DE (1) DE69227322T2 (fr)
WO (1) WO1993023792A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0778493A1 (fr) 1995-11-30 1997-06-11 Eastman Kodak Company Colorants sous forme d'agrégat pour éléments sensibles au rayonnement
US5922523A (en) * 1995-11-30 1999-07-13 Eastman Kodak Company Filter dyes for photographic elements
US5965345A (en) * 1995-12-12 1999-10-12 Eastman Kodak Company Co-dispersion of sensitizing dyes
US6180295B1 (en) 1998-09-11 2001-01-30 Eastman Kodak Company Liquid crystalline filter dyes for imaging elements
US6214499B1 (en) 1998-09-11 2001-04-10 Eastman Kodak Company Liquid crystalline filter dyes for imaging elements
US6245255B1 (en) 1998-09-11 2001-06-12 Eastman Kodak Company Liquid crystalline filter dyes for imaging elements

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6750002B2 (en) 2002-01-28 2004-06-15 Eastman Kodak Company Process for the preparation of concentrated dye-water compositions

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006025A (en) * 1975-06-06 1977-02-01 Polaroid Corporation Process for dispersing sensitizing dyes
US4683193A (en) * 1984-03-21 1987-07-28 Fuji Photo Film Co., Ltd. Process for producing silver halide photographic emulsion

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006025A (en) * 1975-06-06 1977-02-01 Polaroid Corporation Process for dispersing sensitizing dyes
US4683193A (en) * 1984-03-21 1987-07-28 Fuji Photo Film Co., Ltd. Process for producing silver halide photographic emulsion

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0778493A1 (fr) 1995-11-30 1997-06-11 Eastman Kodak Company Colorants sous forme d'agrégat pour éléments sensibles au rayonnement
US5922523A (en) * 1995-11-30 1999-07-13 Eastman Kodak Company Filter dyes for photographic elements
US6183944B1 (en) 1995-11-30 2001-02-06 Eastman Kodak Company Aggregated dyes for radiation-sensitive elements
US6300046B1 (en) 1995-11-30 2001-10-09 Eastman Kodak Company Aggregated dyes for radiation-sensitive elements
US6306567B1 (en) 1995-11-30 2001-10-23 Eastman Kodak Company Aggregated dyes for radiation-sensitive elements
US6342339B2 (en) 1995-11-30 2002-01-29 Eastman Kodak Company Aggregated dyes for radiation-sensitive elements
US5965345A (en) * 1995-12-12 1999-10-12 Eastman Kodak Company Co-dispersion of sensitizing dyes
US6180295B1 (en) 1998-09-11 2001-01-30 Eastman Kodak Company Liquid crystalline filter dyes for imaging elements
US6214499B1 (en) 1998-09-11 2001-04-10 Eastman Kodak Company Liquid crystalline filter dyes for imaging elements
US6245255B1 (en) 1998-09-11 2001-06-12 Eastman Kodak Company Liquid crystalline filter dyes for imaging elements
US6355386B1 (en) 1998-09-11 2002-03-12 Eastman Kodak Company Liquid crystalline filter dyes for imaging elements

Also Published As

Publication number Publication date
EP0640225A1 (fr) 1995-03-01
DE69227322D1 (de) 1998-11-19
JPH07506438A (ja) 1995-07-13
EP0640225B1 (fr) 1998-10-14
DE69227322T2 (de) 1999-03-11
JP3309979B2 (ja) 2002-07-29

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