US3877942A - Method of forming photographic images - Google Patents

Method of forming photographic images Download PDF

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Publication number
US3877942A
US3877942A US463321A US46332174A US3877942A US 3877942 A US3877942 A US 3877942A US 463321 A US463321 A US 463321A US 46332174 A US46332174 A US 46332174A US 3877942 A US3877942 A US 3877942A
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United States
Prior art keywords
surface layer
hardening agent
forming images
percent
binder
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.)
Expired - Lifetime
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US463321A
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English (en)
Inventor
Shigeru Nagatomo
Kiyotaka Hori
Takushi Miyazako
Shinji Sakaguchi
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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Publication of US3877942A publication Critical patent/US3877942A/en
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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
    • G03C1/7614—Cover layers; Backing layers; Base or auxiliary layers characterised by means for lubricating, for rendering anti-abrasive or for preventing adhesion
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/151—Matting or other surface reflectivity altering material
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/162—Protective or antiabrasion layer

Definitions

  • ABSTRACT A method of forming photographic images which comprises developing at above 30C a photographic sensitive material comprising a support having thereon at least one photosensitive emulsion layer and a surface layer comprising a hydrophilic binder and containing a copolymer containing repeating units represented by the formula (I) -CH2CH- and repeating units represented by the formula (II) CH CH l I (II) C0011, C0011;
  • R represents a hydrogen atom or a methyl group
  • M and M each represents a member selected from the group consisting of a hydrogen atom, a lithium atom, a sodium atom, a potassium atom and an ammonium group, whereby the occurrence of reticulation decreasesand anti-adhesive properties are improved.
  • the present invention relates to photographic sensitive materials and particularly to a method of forming photographic images wherein the occurrence of reticulation is very small, high speed processing can be carried out at a high temperaure and anti-adhesive properties are improved.
  • Exposed photographic sensitive materials are generally processed at 30C or less. If the temperature of the processing is increased, it becomes possible to shorten the period of time for processing, because the speed of processing, such as development and fixing of the silver halide or the color development thereof, increases with an increase in the temperature. However, if such a rapid processing is carried out, reticulation of the photosensitive materials in the processing solutions at a high temperature and the quality of images obtained after development remarkably deteriorates.
  • photographic sensitive materials have a surface layer containing a hydrophilic high molecular weight compound such as gelatin as a binder. Therefore, the surface of the photographic sensitive material is easily influenced by the temperature and easily becomes sticky.
  • An object of the present invention is to provide a method of forming photographic images wherein the occurrence of reticulation at high temperature processing is inhibited and the anti-adhesive properties are improved.
  • the present inventors have found that the occurrence of reticulation in development of photographic sensitive materials at high layer containing a specific high molecular weight compound. Furthermore, it has been found that the occurrence of reticulation can be inhibited in providing such a surface layer, even if high speed drying is carried out at production of the photographic sensitive materials.
  • the invention provides a method of forming photographic images which comprises developing at a temperature of above 30C a photographic sensitive material comprising a support having thereon at least one photosensitive emulsion layer and a surface layer comprising a hydrophilic binder and containing a copolymer including repeating units represented by the formula (I) CH2 CH and repeating units represented by the formula (II) CH CH COOM; COOM wherein R represents a hydrogen atom or a methyl group, M and M each represents a member selected from the group consisting of a hydrogen atom. a lithium atom, a sodium atom, a potassium atom and an ammonium group, whereby occurrence of reticulation decreases and the anti-adhesive properties are improved.
  • the high molecular weight compounds used in the present invention are those produced by copolymcrizing styrene or methyl styrene and maleic acid or maleic acid anhydride and hydrolyzing the resulting copolymer, which have repeating units represented by the following general formulae (1) and (II) CH CH COOP l COOM;
  • R represents a hydrogen atom or a methyl group and M and M each represents H, Li, Na, K or NH4.
  • copolymers having these units can contain, if desired, one or more other polymerizable monomers so long as the hydrophilic properties thereof are not injured.
  • polymerizable monomer components include the alkyl esters of acrylic acid and methacrylic acid (e.g., methyl methacrylate, ethyl acrylate, hydroxyethyl acrylate, propyl acrylate, cyclohexyl acrylate, Z-ethylhexyl acrylate, decyl acrylate, B-cyanoethyl acrylate, B-chloroethyl acrylate, 2-ethoxyethyl acrylate, sulfopropyl methacrylate and the like), vinyl ethers (e.g., methylvinyl ether, butyl vinyl ether, oleyl vinyl ether and the like), vinyl ketones (e.g., methyl vinyl ketone, ethyl vinyl ketone and the like),
  • acetone, methanol, isopropanol, methyl ethyl ketone, tetrahydrofuran, dimethylformamide, benzene or a mixture thereof can be used as a solvent.
  • the quantity of the monomers charged can be suitably varied, for example, the monomers can be used in a range of about 20 to 150 percent by weight to the solvent.
  • conventional radical polymeriza tion catalysts such as azobisisobutyronitrile, 2,2'-azobis-(2,4-valeronitrile 1,1 -azobis- (cyclohexanel -carbonitrile), 2,2-azobis(4-methyl-2,4- dimethyl valeronitrile) and benzoyl peroxide can be effectively used.
  • the amount of the catalysts is about 0.1 to 5 percent by weight, and preferably is 0.5 to 2.0 percent by weight based on the weight of the monomers from an operational viewpoint.
  • the polymerization reaction is carried out by heating at about 60 to 80C in an inert atmosphere, e.g., a nitrogen atmosphere, for about 3 to 6 hours.
  • the produced polymers are used after neutralizing or hydrolyzing with an aqueous alkali solution, such as lithium hydroxide, sodium hydroxide or potassium hydroxide, of a concentration of about 2 to 30 percent by weight, preferably 10 to percent by weight.
  • an aqueous alkali solution such as lithium hydroxide, sodium hydroxide or potassium hydroxide
  • the content of maleic acid in the copolymer range from about 40 to 60 percent on a molar basis, because, the viscosity of a coating solution is too high during the application thereof for forming the surface layer if the maleic acid content is too high, while the compatibility of the copolymer with gelatin deteriorates if the maleic acid content is too low.
  • a suitable amount of the copolymerizable monomer which can be present can range from about 0.5 to 30 mole percent, preferably 1 to 10 mole per-,
  • the molecular weight of the copolymers is not limited and can vary widely, copolymers having a molecular weight of about 10 to 10 and particularly 10 to 5 X 10" can be suitably used.
  • Suitable polymerization procedures which can be used are well known in the prior art, for example, as disclosed in W. R. Sorensen et al., Preparative Methods of Polymer Chemistry, John Wiley and Sons, New York (1961).
  • resulting copolymers are used as a component of the surface layer.
  • a preferred amount thereof ranges arom about 5 to percent by weight based on the total weight of the binder in the top layer. Because, if the amount is less than about 5 percent, a sufficient effect can not be obtained and if the amount is above about 80 percent, the surface layer dissolves on development in alkaline developers.
  • a suitable thickness for the top layer generally ranges from about 0.1 to So, preferably 0.3 to 3,u..
  • the surface layer can also contain matting agents such as polystyrene, polymethyl methacrylate, silica, starch powder, zinc carbonate, glass beads, cadmium carbonate, polyethyl acrylates, copoly-methyl methacrylate-butylacrylate, strontium carbonate, magnesium oxide barium sulfate-strontium sulfate, titanium oxide, zirconium oxide a silver halide such as silver bromide, polystyrene, cellulose triacetate, a calcium salt or magnesium salt of an acid such as an aliphatic acid, an aromatic acid, an aromatic dicarboxylic acid such as terephthalic acid, a polycarbonate and the like.
  • matting agents such as polystyrene, polymethyl methacrylate, silica, starch powder, zinc carbonate, glass beads, cadmium carbonate, polyethyl acrylates, copoly-methyl methacrylate-butylacrylate, strontium carbonate
  • the most preferred matting agents are silica, polymethyl methacrylate, a silver halide, and barium sulfate-strontium sulfate.
  • the matting agents those having a particle size ranging from about 0.3 to 10a, particularly 0.5 to 3p. are preferably used. In using these matting agents, they are used in the amount of about 0.1 to 10 percent by weight and preferably 0.5 to 3 percent by weight based on the total weight of the binders in the surface layer.
  • the binder of the surface layer can be selected, if desired, from synthetic and natural high molecular weight compounds such as gelatin, gelatin derivatives, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylamide, polyacrylic acid, polyacrylates, casein, agar agar, albumin, alginic acid, carboxycellulose alkyl esters, hydroxyethyl cellulose, carboxyalkyl cellulose and the like.
  • gelatin and the derivatives thereof are more preferable.
  • organic solvents such as methanol, ethanol, propanol,
  • acetone methyl ethyl ketone, etc., or mixtures thereof are used.
  • water is advantageously used.
  • hardening agents as described in, e.g., C. E. K. Mees and T. H. James, The Theory ofthe Photographic Process, 3rd ed., pages 55 60, Macmillan Co., 1966) and the hardening agents described in U.S. Pat. No. 3,316,095 are preferably used at application.
  • these hardening agents those of an aldehyde type (including the mucochloric acid type, and the aldehyde precursor type), an active vinyl type, an active halogen.
  • Aldehyde type a carbodiimide type, an isoxazole type, an epoxy type, an aziridine type and an inorganic type provide better results. Particularly, the following hardening agents exhibit particularly excellent results.
  • Aldehyde type a carbodiimide type, an isoxazole type, an epoxy type, an aziridine type and an inorganic type provide better results. Particularly, the following hardening agents exhibit particularly excellent results.
  • Mucochloric acid mucobromic acid, mucophenoxychloric acid, mucophenoxy bromic acid, formaldehyde,
  • dimethylol urea trimethylolmelamine
  • 1,3-bis- [(diallylamino)-methyll-urea, 1,3-bis- (piperidinomethyl)-urea glyoxal, monomethylglyoxal, 2,3-dihydro-1,4-dioxane, 2,3-dihydroxy-5-methyl-l ,4- dioxane, succinaldehyde, 2,5-dimethoxytetrahydrofuran and glutaraldehyde.
  • Chromium alum and chromium acetate Chromium alum and chromium acetate.
  • hardening agents can be added using conventional methods. For example, a hardening agent dissolved in water or an organic solvent is directly added to the composition used to form the surface layer, or a hardening agent is added in a large amount to an another layer so as to diffuse into the surface layer.
  • these hardening agents depends upon a desired objects, they can be used in the amount of about 2 to about 80 mg and preferably 5 to mg per gram of gelatin.
  • sodium dodecyl benzene sulfonate sodium N-oleyl-N-methyltaurine, sodium l4-p-nonyl-phenyl-5,8,l 1,14-tetraoxatetradecane sulfonate and N-tetradecyl-N,N-dimethylammonioacetate can be used.
  • the contents of the high molecular weight compounds, gelatin, the matting agents, lubricating agents, antistatic agents, the hardening agents and the coating assistants in the present invention can be varied over a broad range depending on the requirements of quality and end-use of the photographic sensitive materials.
  • the specific agents and the optimum amounts thereof can be easily determined by persons skilled in the art.
  • the top layer of this invention is applicable to black and white, multi layer color, X-ray and the like photographic materials utilizing any layer structure.
  • the top layer can be a surface layer on the photosensitive layer side of the support or a surface layer on the opposite side of the support to the photosensitive layer.
  • any developer can be used if it can reduce halide particles.
  • developers containing polyhydroxybenzenes, N-alkylaminophenols, l-phenyl- 3-pyrazolidones or a mixture thereof can be used.
  • polyhydroxybenzenes include hydroquinone, pyrocatechol, pyrogallol and the like.
  • N- monoalkylaminophenols include N- methylaminophenol, N-ethylaminophenol and the like.
  • l-phenyl-3-pyrazolidones include l-phenyl-3-pyrazolidone, l-phenyl-4,4-dimethyl-3- pyrazolidone and the like.
  • developers containing p-phenylenediamine derivatives such as 4-amino-N,N-diethylaniline.
  • -N-ethyl-N-(B-hydroxyethyl)-aniline and the like can be used as a developing agent.
  • the yield was 96.2g (95.3 percent). Then the high molecular weight compound was hydrolyzed using an aqueous solution of sodium hydroxide to produce a 20 percent solution. The pH was 6.3. As the result of a determination of the viscosity, the solution had a viscosity of; sp/c 0.61 (30C).
  • the reaction product was reprecipitated using water and dried in a vacuum until a constant weight was obtained.
  • the yield was g (91.0 percent).
  • EXAMPLE 1 On a triacetyl cellulose base film having a subbing layer, a red-sensitive emulsion layer, an intermediate layer, a green-sensitive emulsion layer, a yellow filter IO layer, a blue-sensitive emulsion layer and a top layer were formed by application, wherein these layers contained the additives shown in Table 1. However, the top layer was formed by preparing compositions l, 2, 3, 4
  • EXAMPLE 2 Compound 2 was added to each sample of Example 1 as follows, and the samples were produced by application and drying.
  • Example 3 After these samples were stored at C and humidity of 60 percent for 1 week, the same processing as in Example 1 was carried out, and then reticulation was observed. The degree of the occurrence of reticulation is shown in Table 3.
  • EXAMPLE 3 On a polyethylene terephthalate base film having a subbing layer, a red-sensitive emulsion layer, a greensensitive emulsion layer, a yellow filter layer, a bluesensitive emulsion layer and a top layer were formed by application using the spectral sensitizers, the stabilizer and the coating assistants shown in Table 1 and 20 mg of mucochloric acid per gram of the binder as a hardening agent.
  • the top layer was formed by preparing samples 1, 2, 3 and 4 by mixing silver halide particles and barium sulfate as matting agents, liwuid paraffin as a lubricating agent and Compound 3 in an amount of O, 5, 30 or percent by weight based on the binder weight in addition to the above-described coating assistants and the hardening agent, applying the mixture and drying (the thickness of the top layer being 1 2,u.).
  • compositions of each processing bath were produced using known methods (as disclosed in US. Pat. No. 3,723,125).
  • composition of the prehardening bath was as follows.
  • EXAMPLE 4 In this example, samples corresponding to Sample 1 and Sample 2 of Example 2 were prepared except that silicon dioxide and polymethyl methacrylate particles were not used. Sample 6 and Sample 7 were prepared in the same manner as in Sample 1 and Sample 3 of Example 2.
  • the resulting Sample 6 and Sample 7 and Sample 1 ,and Sample 2 of Example 2 were tested with respect to the degree of adhesion.
  • the adhesion test was carried out as follows. Each sample was cut to make two sheets of 2cm X 2cm. These sheets were individually placed at a specific temperature and a specific humidity and were placed so as to not contact each other. After being maintained at such conditions for 2 days, the two sheets of the sample were superposed so that top layer of one faced the back layer of the other. After a weight of 200g was put on the superposed sheets (5Og/cm the sheets were kept at the same conditions for 1 day. Then the sheets were peeled off and the area of adhesion was measured. In Table 5, the percentages of the area of adhesion based on the total area are shown.
  • a method of forming photographic images which comprises developing at above 30C a photographic one material comprising a support having thereon at least on photosensitive emulsion layer and a surface layer comprising a hydrophilic binder and containing a copolymer including repeating units represented by the formula (l) CH2 ca and repeating units represented by the formula (H) wherein R represents a hydrogen atom or a methyl group, and M and M each represents a member selected from the groupconsisting of a hydrogen atom, a lithium atom, a sodium atom, a potassium atom and an ammonium group, whereby occurrence of reticulation decreases and anti-adhesive properties are improved.
  • hydrophilic binder comprises a natural or synthetic high molecular weight material.
  • binder is gelatin, albumin, agar agar, a gelatin derivative, a cellulose derivative, polyvinyl alcohol, a partial ester of polyvinyl alcohol, polyacrylamide, polyvinyl pyrrolidone, polyacrylic acid or a polyacrylate.

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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)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US463321A 1973-04-27 1974-04-23 Method of forming photographic images Expired - Lifetime US3877942A (en)

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GB (1) GB1437865A (en, 2012)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3938999A (en) * 1974-03-30 1976-02-17 Fuji Photo Film Co., Ltd. Antistatic photographic sensitive materials
US4008087A (en) * 1974-08-05 1977-02-15 Fuji Photo Film Co., Ltd. Photographic light-sensitive material
US4142894A (en) * 1976-07-08 1979-03-06 Fuji Photo Film Co., Ltd. Method for forming images
US4166050A (en) * 1975-12-01 1979-08-28 Fuji Photo Film Co., Ltd. Method of increasing the viscosity of photographic coating solutions
US4291120A (en) * 1979-02-15 1981-09-22 Fuji Photo Film Co., Ltd. Heat developable photosensitive material
US4367284A (en) * 1980-05-26 1983-01-04 Minnesota Mining And Manufacturing Company Photographic elements with improved surface characteristics
US4614708A (en) * 1981-11-23 1986-09-30 Agfa-Gevaert, N.V. Method for the preparation of stable aqueous dispersions of polymer beads and the use of these dispersions in photographic elements

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4404276A (en) 1982-06-14 1983-09-13 Eastman Kodak Company Polymer compositions containing crosslinked silicone polycarbinol and having a low coefficient of friction
USRE32514E (en) * 1982-06-14 1987-10-06 Eastman Kodak Company Polymer compositions having a low coefficient of friction
US4473676A (en) * 1982-06-14 1984-09-25 Eastman Kodak Company Polymer compositions having a low coefficient of friction
DK666988A (da) * 1987-11-30 1989-05-31 Du Pont Fotografisk film med antistatisk bagsidelag

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3468664A (en) * 1959-04-10 1969-09-23 Eastman Kodak Co Heat processable photographic elements having water vapor-impermeable protective outer layer
US3503743A (en) * 1966-05-26 1970-03-31 Diagravure Film Mfg Corp Protection of hydrophilic films,layers,and products thereof
US3591379A (en) * 1968-04-09 1971-07-06 Eastman Kodak Co Photographic overcoat compositions and photographic elements
US3597208A (en) * 1966-03-09 1971-08-03 Fuji Photo Film Co Ltd Process for producing photographic light-sensitive elements
US3816136A (en) * 1972-07-17 1974-06-11 Eastman Kodak Co Photographic element and process of developing

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3468664A (en) * 1959-04-10 1969-09-23 Eastman Kodak Co Heat processable photographic elements having water vapor-impermeable protective outer layer
US3597208A (en) * 1966-03-09 1971-08-03 Fuji Photo Film Co Ltd Process for producing photographic light-sensitive elements
US3503743A (en) * 1966-05-26 1970-03-31 Diagravure Film Mfg Corp Protection of hydrophilic films,layers,and products thereof
US3591379A (en) * 1968-04-09 1971-07-06 Eastman Kodak Co Photographic overcoat compositions and photographic elements
US3816136A (en) * 1972-07-17 1974-06-11 Eastman Kodak Co Photographic element and process of developing

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3938999A (en) * 1974-03-30 1976-02-17 Fuji Photo Film Co., Ltd. Antistatic photographic sensitive materials
US4008087A (en) * 1974-08-05 1977-02-15 Fuji Photo Film Co., Ltd. Photographic light-sensitive material
US4166050A (en) * 1975-12-01 1979-08-28 Fuji Photo Film Co., Ltd. Method of increasing the viscosity of photographic coating solutions
US4142894A (en) * 1976-07-08 1979-03-06 Fuji Photo Film Co., Ltd. Method for forming images
US4291120A (en) * 1979-02-15 1981-09-22 Fuji Photo Film Co., Ltd. Heat developable photosensitive material
US4367284A (en) * 1980-05-26 1983-01-04 Minnesota Mining And Manufacturing Company Photographic elements with improved surface characteristics
US4614708A (en) * 1981-11-23 1986-09-30 Agfa-Gevaert, N.V. Method for the preparation of stable aqueous dispersions of polymer beads and the use of these dispersions in photographic elements

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DE2419582A1 (de) 1974-11-21
JPS5321646B2 (en, 2012) 1978-07-04
JPS49135619A (en, 2012) 1974-12-27
GB1437865A (en, 2012) 1976-06-03

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