EP0370405A1 - Matériel photographique photosensible, à l'halogénure d'argent et méthode pour la préparation d'une dispersion de particules distinctes de polymères insoluble dans l'eau, dans des compositions aqueuses - Google Patents

Matériel photographique photosensible, à l'halogénure d'argent et méthode pour la préparation d'une dispersion de particules distinctes de polymères insoluble dans l'eau, dans des compositions aqueuses Download PDF

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Publication number
EP0370405A1
EP0370405A1 EP89121311A EP89121311A EP0370405A1 EP 0370405 A1 EP0370405 A1 EP 0370405A1 EP 89121311 A EP89121311 A EP 89121311A EP 89121311 A EP89121311 A EP 89121311A EP 0370405 A1 EP0370405 A1 EP 0370405A1
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EP
European Patent Office
Prior art keywords
polymer
weight
water
photographic material
units derived
Prior art date
Legal status (The legal status 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 status listed.)
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Application number
EP89121311A
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German (de)
English (en)
Inventor
Mauro Besio
Sergio Massirio
Michele Zunino
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
3M Co
Original Assignee
Minnesota Mining and Manufacturing Co
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 Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Publication of EP0370405A1 publication Critical patent/EP0370405A1/fr
Withdrawn legal-status Critical Current

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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
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/95—Photosensitive materials characterised by the base or auxiliary layers rendered opaque or writable, e.g. with inert particulate additives

Definitions

  • the present invention relates to a silver halide photographic light-sensitive material having incorporated in a gelatin layer thereof discrete particles of a water-­insoluble polymeric matting agent and a process for pre­paring a dispersion of discrete particles of a water-in­soluble polymer in aqueous compositions.
  • water-insoluble matting agents have been used in top or back hydrophilic layers of silver halide light-sensitive materials to prevent adhesion when materials are stored in rolls, cartridges or cassettes in conditions of relatively high humidity and temperature, to prevent electrostatic charges by re­ducing the area of contact of the photographic material, to prevent the formation of Newton's rings during print­ing and enlargement, or to decrease the occurrence of scratches during storage or packing of the photographic material.
  • matting agents insoluble in neutral or acidic solutions and soluble in alkaline medium have been described in the art.
  • alkali-soluble matting agents consisting of methacrylic acid - methylmethacrylate copolymers have been described in US Pat. Nos. 2,391,181, 2,992,101, 3,767,448 and 4,142,894, and in British Pat. No. 878,520, and copolymers of styrene and ⁇ , ⁇ -ethylenically unsatu­rated carboxy containing monomers have been described in British Pat. No. 1,055,713.
  • Such matting agents are in­corporated in the photographic layers in the form of dis­crete particles by dispersing a solution of the matting agent in a water-immiscible organic solvent in an aqueous gelatin solution, eliminating the organic solvent, and then introducing the obtained dispersion into the coating composition of the photographic layer.
  • Organic solvents or combinations thereof have been studied with the co­polymers of methacrylic acid and methylmethacrylate, the basic solvent being butanol and mixture thereof with oth­er solvents. Since butanol is a solvent with low vola­tility it must be removed by cooling the dispersion and washing with deionized water.
  • Alkali-soluble matting agents consisting of methacrylic acid - ethylmethacrylate copolymers containing from 20 to 50 % by weight of meth­acrylic acid have been described in US Pat. No. 4,447,525. These copolymers dissolve in high concentra­tions in high volatile organic solvent such as ethyl­acetate, a solvent which can be easily removed by evapo­ration from the dispersion of the polymer in aqueous gel­atin.
  • the matting agents are characterized by the average particle sizes (APS) of their discrete particles and in the patents there are teachings on how to control the APS in the process of synthesis thereof.
  • APS average particle sizes
  • matting agents Another characteristic of matting agents is their particle size distribution (PSD), in particular the size measure of the higher discrete particles present in the dispersion.
  • PSD particle size distribution
  • Processes described in the art for the syn­thesis of matting agent dispersions may result in the formation of huge particles exceeding 10 ⁇ m of diameter.
  • the presence of such huge particles of matting agents may cause undesirable side effects such as disturbance of uniform coating of the photographic material and distur­bance of distinct layer relationship of a plurality of superposed layers of the photographic material.
  • Matting agents dispersions can be obtained having particle size distribution (PSD) not exceeding 10 ⁇ m by (1) dissolving in a low-boiling water insoluble organic solvent a polymer, derived from the polymerization through ethylenically unsaturated groups, comprising from 0.05% to 50% by weight of repeating units derived from ethylenically unsaturated monomers having at least one carboxyl group thereon and from 99.95% to 50% by weight of repeating units derived from ethylenically unsaturated monomers capable of forming hydrophobic homopolymers, (2) adding to the first resulting solution a second solution of alkali metal compound in water to transform some or all of the carboxyl groups into alkali metal carboxylate groups, and (3) dispersing the second resulting solution in aqueous compositions.
  • PSD particle size distribution
  • carboxyl group means a group capable to undergo the transformation to alkali metal carboxylate group as, for example, a carboxylic acid, an anhydride and the like.
  • the matting agent dispersions according to this in­vention comprise discrete polymeric particles having di­ameters of maximum 10 ⁇ m and comprising from 0 to 49.95 percent by weight of repeating units derived from ethyl­enically unsaturated monomers having carboxyl groups thereon, from 0.05 to 10 percent by weight of repeating units derived from ethylenically unsaturated monomers having alkali metal carboxylate groups thereon, the sum of units derived from ethylenically unsaturated monomers having alkali metal carboxylate groups thereon and units derived from ethylenically unsaturated monomers having carboxyl groups thereon representing at most 50 percent by weight of the polymer, and the remaining polymer weight percentage derived from ethylenic unsaturated monomers capable of forming hydrophobic homopolymers.
  • Said matting agent dispersions can be introduced into the coating compositions of the outer light-in­sensitive layer of a silver halide light-sensitive photo­graphic material without causing either physical or sen­sitometric harmful effects.
  • the present invention relates to a pro­cess for preparing a dispersion of discrete particles of a water-insoluble polymer in aqueous compositions com­prising:
  • Examples of ethylenic unsaturated monomers having carboxyl groups thereon from which derive the repeating units (a) of the polymer above include acrylic acid, methacrylic acid, maleic acid (including monosubstituted maleates such as monomethyl maleate, monoethyl maleate and monophenyl maleate), itaconic acid (including mono­substituted itaconate such as monomethyl itaconate, mono­ethyl itaconate and monobutyl itaconate), fumaric acid (including monosubstituted fumarate such as monomethyl fumarate and monoethyl fumarate), crotonic acid, citra­conic acid, N-(meth)-acryloylamino acids such as N-acryl­oylglycine, N-methacryloylglycine, N-acryloylalanine, N-methacryloylalanine and N-acryloylproline, vinylbenzoic acid, maleic acid monoamide,
  • ethylenic unsaturated monomers from which derive the repeating units (b) of the polymer above include acrylic acid esters such as methyl acrylate, eth­yl acrylate, n-butyl acrylate and phenyl acrylate, meth­acrylic acid esters such as methyl methacrylate, ethyl methacrylate, isopropyl methacrylate and p-chlorophenyl methacrylate, styrenes such as styrene, methylstyrene, ⁇ -methylstyrene, chloromethylstyrene and bromostyrene, vinyl esters such as vinyl benzoate, vinylphenyl acetate and vinyl naphthoate, vinyl ethers such as allyl butyl ether, methoxyethyl vinyl ether and phenyl vinyl ether, olefins such as ethylene, propylene, 1-butene and 1-pen­tene, uns
  • methacrylic acid is particularly preferable as the ethylenic unsaturated monomers having carboxyl groups thereon from which derive the repeating units (a) of the polymer above and methacrylic acid esters such as methyl methacrylate and ethyl methacrylate are particularly preferable as ethylenic unsaturated monomers from which derive the repeating units (b) of the polymer above.
  • the polymer for use in the process of the present invention is preferably represented by the formula (I) wherein m represents from 0.05 to 50 % by weight of the polymer, n represents the remaining % by weight of the polymer and R represents methyl or ethyl.
  • Said polymer is prepared from the polymerization through ethylenically unsaturated groups of the monomers used in the present invention, using any conventional polymerization mechanism, preferably by free radical pol­ymerization.
  • the free radical polymerization is carried out by heating at a proper temperature (which usually does not exceed 100°C and preferably is between 50°C and 100°C) in a proper solvent (usually ethanol or methanol) a mixture of the two monomers in a proper con­centration with respect to the solvent (usually at a con­centration that does not exceed 40% by weight of the two monomers with respect to the solvent, preferably between 15% to 30%) in presence of a polymerization catalyst (for example of the free radical type, such as benzoyl perox­ide or cumene hydroperoxide, or of the azoic type, such as ⁇ , ⁇ ′-azobisisobutyronitrile).
  • the obtained polymer can be then separated from the reaction mixture for example by precipitating into a non-solvent, such as
  • Low-boiling substantially water-immiscible organic solvents for use in the process of the present invention include halogenated hydrocarbons such as chloroform, di­chloromethane, carbon tetrachloride, 1,1-dichloromethane, 1,2-dichloroethane and 1,1,1-trichloroethane, aliphatic esters such as ethyl acetate, butyl acetate and isopropyl acetate, aromatic hydrocarbons such as benzene, toluene and xilene, aliphatic hydrocarbons such as pentane and n-hexane, aliphatic ketons such as methyl ethyl ketone and methyl isobutyl ketone, higher aliphatic alcohols such as n-butanol and isobutanol, and the like.
  • halogenated hydrocarbons such as chloroform, di­chloromethane, carbon tetrach
  • Said or­ganic solvents have a boiling point preferably of less than 150°C, more preferably of less than 100°C, and a solubility in water at 20°C preferably of less than 20 grams per liter, more preferably of less than 10 grams per liter.
  • the alkali metal compounds for use in the process of the present invention are basic compounds able to trans­form carboxyl groups of the polymer above into alkali metal carboxylate groups.
  • said basic alkali metal compounds are alkali metal hydroxides such as sodi­um hydroxide and potassium hydroxide, but other basic alkali metal compounds can be advantageously used such as sodium carbonate, sodium ethoxide, sodium methoxide and the like.
  • the organic solution including a polymer comprising (a) repeating units derived from an ethylenic unsaturated monomer having carboxyl groups thereon, said units com­prising from 0 to 49.95 % by weight of said polymer, (b) repeating units derived from an ethylenic unsaturated monomer having alkali metal carboxylate groups thereon, said units comprising from 0.05 to 10 % by weight of said polymer, the sum of units derived from an ethylenic un­saturated monomer having alkali metal carboxylate groups thereon and units derived from an ethylenic unsaturated monomer having carboxyl groups thereon representing at most 50 percent by weight of the polymer, and (c) repeat­ing units derived from an ethylenic unsaturated monomers capable of forming hydrophobic homopolymers, said units forming the remaining polymer weight percentage, is dis­persed in water.
  • the dispersion is then added with a sur­face active agent or, preferably, an aqueous hydrophilic colloid solution.
  • a sur­face active agent or, preferably, an aqueous hydrophilic colloid solution.
  • the hydrophilic colloid is preferably gelatin, but also gelatin derivatives and other polymeric compounds, such as polyacrylamide and polyvinyl alcohol, can be used.
  • the organic solvent is eliminated from the dispersion by cooling, noodling and washing the dispersion with pure water or by heating, as known in the art.
  • the polymers above become dispersed in the aqueous solution of the hydrophilic colloid in the form of finely divided particles having diameters from 0.5 to 10 ⁇ m with absence of particles having diameters exceeding 10 ⁇ m. Said dispersions are introduced into the coating composi­tion of the outer light-insensitive layer of a silver halide light-sensitive material.
  • the present inven­tion relates to a photographic material comprising a sup­port base, one or more light-sensitive gelatin silver halide emulsion layers and an outer non lightsensitive gelatin layer comprising discrete particles of a water-­insoluble polymeric matting agent, wherein said polymeric matting agent comprises:
  • Said water-insoluble polymeric matting agent is preferably represented by the general formula (II) wherein M represents an alkaline metal, preferably Na and K, R represents methyl or ethyl, x represents from 0 to 49.95% by weight of the polymer, y represents from 0.05 to 10 % by weight of the polymer, x + y represents at most 50 % by weight of the polymer, and z represents the remaining polymer weight percentage.
  • the maximum percentage by weight of repeating units derived from the ethylenic unsaturated monomer having carboxyl groups thereon in the polymers of the present invention represents the limit beyond which the polymer becomes soluble in neutral or acid aqueous gelatin solu­tions.
  • Total sol­ubility in the alkaline processing solutions for silver halide light-sensitive photographic materials can be ap­proached for polymers having higher percentages of re­peating units derived from the ethylenic unsaturated monomer having carboxyl groups thereon, while partial solubility or insolubility can be achieved for polymers having lower percentages of repeating units derived from the ethylenic unsaturated monomer having carboxyl groups thereon.
  • water-insoluble and alkali-soluble matting agents of the present invention are those com­prising discrete particles of a polymer represented by the following general formula (III) wherein M represents an alkaline metal, R represents methyl or ethyl, x′ represents from 20 to 49.95 % by weight of the polymer, y′ represents from 0.05 to 10 % by weight of the polymer, x′ + y′ represents at most 50 % by weight of the polymer, and z′ represents the remaining polymer weight percentage. More preferably, in the formu­la (III) above R represents an ethyl group.
  • water insoluble and alkali-in­soluble matting agents of the present invention are those comprising discrete particles of a polymer represented by the following general formula (IV) wherein M represents an alkaline metal, R represents methyl or ethyl, x ⁇ represents from 0 to 19.95 % by weight of the polymer, y ⁇ represents from 0.05 to 10 % by weight of the polymer, x ⁇ + y ⁇ represents at most 20 % by weight of the polymer, and z ⁇ represents the re­maining polymer weight percentage.
  • M represents an alkaline metal
  • R represents methyl or ethyl
  • x ⁇ represents from 0 to 19.95 % by weight of the polymer
  • y ⁇ represents from 0.05 to 10 % by weight of the polymer
  • x ⁇ + y ⁇ represents at most 20 % by weight of the polymer
  • z ⁇ represents the re­maining polymer weight percentage.
  • the matting agents of the present invention are incorporated into the outer layer of the photographic material. They can be for instance incorporated into the surface protective layer coated on the silver halide emulsion layers, or into the backing layer coated on the support base on the side opposite to that containing the light-sensitive layers, or on both sides. It is more pre­ferred, in any case, to incorporate the matting agents of the present invention into outer protective layer.
  • the matting agents are incorporated in a quantity of about 50 to about 600 mg., more preferably from about 150 to about 400 mg. per square meter of the surface lay­er.
  • the binding agent of such layer preferably is gela­tin, but treated gelatins like the so-called acid or ba­sic gelatins, the gelatins treated with enzymes, gelatin derivatives and modified gelatins can also be used.
  • the surface layer of the photographic material can also contain matting agents characterized by the water-­insoluble and alkali-insoluble discrete particles of the polymer represented by the formula (IV) above or water-­insoluble and alkali-insoluble discrete particles of mat­ting agents, known in the art, such as for example fine silica, polymethylmethacrylate, starch particles, and the like.
  • Such water-insoluble and alkali-insoluble discrete particles of matting agents are usually used in the outer layer in a quantity lower than that of the water-in­soluble and alkali-soluble discrete particles of the pol­ymer represented by the formula (III) above, for instance in a quantity up to 50 mg. per square meter, preferably from 5 to 10 mg. per square meter, since they remain in the photographic material after processing.
  • the matting agents of the present invention can be used in color photographic materials which comprise a plurality of hydrophilic (i. e. permea­ble to the water photographic processing solutions) emul­sion layers containing silver halides dispersed in gela­tin, associated with auxiliary hydrophilic gelatin lay­ers, interlayers, antihalo layers, backing layers, said plurality of layers being coated onto a hydrophobic sup­port base.
  • hydrophilic i. e. permea­ble to the water photographic processing solutions
  • emul­sion layers containing silver halides dispersed in gela­tin, associated with auxiliary hydrophilic gelatin lay­ers, interlayers, antihalo layers, backing layers, said plurality of layers being coated onto a hydrophobic sup­port base.
  • such silver halide emulsions When used for color reproduction, such silver halide emulsions are sensitive or (sensitized) to the blue and associated with non-diffusing yellow-forming couplers (upon color development with p-phenylene diamine after exposure), or are sensitized to the green and associated with non-diffusing magenta(blue red)forming couplers, or sensitized to the red and associated with non-diffusing cyan(blue-green)forming couplers.
  • the photographic element can contain silver halide emulsions, chemical sensitizers, spectral sensitizers and desensitizers, optical brighteners, antifoggants and sta­bilizers, couplers, acutance dyes, hydrophilic colloids and gelatin substituents, coating aids, hardeners, plasticizers and antistatic agents, as known to the man skilled in the art and can be prepared by following known coating techniques applied to known support bases, as described in Research Disclosure, December 1978, 17643, which is incorporated herein as reference.
  • the photographic materials of this invention after exposure, are processed to form a visible image upon as­sociation of the silver halide with an alkaline water medium in the presence of a developing agent contained in the medium or in the material, as known in the art.
  • the processing comprises at least a color developing bath and, optionallyly, a pre-hardening bath, a neutralizing bath, a first (black and white) developing bath, etc.
  • These and other baths which complete the photographic processing e. g. bleaching, fixing, bleach-fixing, intensifying, stabiliz­ing and washing baths
  • Dispersion B and C were prepared using, respectively, 1 ml. and 0.6 ml. of sodium hydroxide 1N and containing discrete parti­cles of a polymer corresponding to the formulas
  • Dispersion E and F were prepared using, respectively, 0.4 ml. and 2.0 ml. of sodium hydroxide 1N and containing discrete parti­cles of a polymer corresponding to the formulas
  • Dispersion H was prepared using a n-butanol solution instead of the ethyl acetate-water solution.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
EP89121311A 1988-11-25 1989-11-17 Matériel photographique photosensible, à l'halogénure d'argent et méthode pour la préparation d'une dispersion de particules distinctes de polymères insoluble dans l'eau, dans des compositions aqueuses Withdrawn EP0370405A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT8822736A IT1227929B (it) 1988-11-25 1988-11-25 Materiale fotografico agli alogenuri d'argento sensibili alla luce e procedimento per preparare una dispersione in composizioni acquose di particelle discrete di polimeri insolubili in acqua
IT2273688 1988-11-25

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EP0370405A1 true EP0370405A1 (fr) 1990-05-30

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EP89121311A Withdrawn EP0370405A1 (fr) 1988-11-25 1989-11-17 Matériel photographique photosensible, à l'halogénure d'argent et méthode pour la préparation d'une dispersion de particules distinctes de polymères insoluble dans l'eau, dans des compositions aqueuses

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EP (1) EP0370405A1 (fr)
JP (1) JPH02185504A (fr)
IT (1) IT1227929B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5563226A (en) * 1994-10-28 1996-10-08 Eastman Kodak Company Process for making photographic polymeric matte bead particles
US6033839A (en) * 1998-05-20 2000-03-07 Eastman Kodak Company Polymeric matte particles

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20230025550A1 (en) * 2019-12-19 2023-01-26 Kuraray Co., Ltd. Ionomer resin, resin sheet, and laminated glass

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3296172A (en) * 1963-02-28 1967-01-03 Du Pont Preparing aqueous polymer dispersions in presence of polar liquids
GB1291392A (en) * 1969-03-07 1972-10-04 Du Pont Aqueous dispersions
US4094848A (en) * 1975-05-20 1978-06-13 Fuji Photo Film Co., Ltd. Process for producing finely divided porous polymer particles
GB2078992A (en) * 1980-07-01 1982-01-13 Fuji Photo Film Co Ltd Silver halide photographic light-sensitive material and method of processing
US4447525A (en) * 1981-09-23 1984-05-08 Minnesota Mining And Manufacturing Company Process for providing a matt surface on a photographic material and photographic material provided with such matt surface

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3296172A (en) * 1963-02-28 1967-01-03 Du Pont Preparing aqueous polymer dispersions in presence of polar liquids
GB1291392A (en) * 1969-03-07 1972-10-04 Du Pont Aqueous dispersions
US4094848A (en) * 1975-05-20 1978-06-13 Fuji Photo Film Co., Ltd. Process for producing finely divided porous polymer particles
GB2078992A (en) * 1980-07-01 1982-01-13 Fuji Photo Film Co Ltd Silver halide photographic light-sensitive material and method of processing
US4447525A (en) * 1981-09-23 1984-05-08 Minnesota Mining And Manufacturing Company Process for providing a matt surface on a photographic material and photographic material provided with such matt surface

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5563226A (en) * 1994-10-28 1996-10-08 Eastman Kodak Company Process for making photographic polymeric matte bead particles
US6033839A (en) * 1998-05-20 2000-03-07 Eastman Kodak Company Polymeric matte particles

Also Published As

Publication number Publication date
JPH02185504A (ja) 1990-07-19
IT1227929B (it) 1991-05-14
IT8822736A0 (it) 1988-11-25

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