US3713829A - Photographic light sensitive material containing copolymer layer - Google Patents

Photographic light sensitive material containing copolymer layer Download PDF

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Publication number
US3713829A
US3713829A US00188701A US3713829DA US3713829A US 3713829 A US3713829 A US 3713829A US 00188701 A US00188701 A US 00188701A US 3713829D A US3713829D A US 3713829DA US 3713829 A US3713829 A US 3713829A
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US
United States
Prior art keywords
copolymer
sensitive material
photographic
photographic light
percent
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
Application number
US00188701A
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English (en)
Inventor
F Nishio
D Nishio
Y Nakajima
S Watarai
K Ohkubo
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.)
Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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Publication date
Application filed by Fuji Photo Film Co Ltd filed Critical Fuji Photo Film Co Ltd
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
    • G03C1/053—Polymers obtained by reactions involving only carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52—Amides or imides
    • 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
    • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
    • 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
    • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
    • G03C1/043—Polyalkylene oxides; Polyalkylene sulfides; Polyalkylene selenides; Polyalkylene tellurides
    • 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
    • Y10S430/131—Anticurl layer

Definitions

  • R and R can be H or CH R can be an alkyl group having one to three carbon atoms, x and y represent positive integers, and Z represents-one of:
  • n is l-3, exhibits reduced curling upon exposure to moisture.
  • the sensitivity at the foot portion of the characteristic curve B of the emulsion containing the high molecular weight compound is substantially 'in-. creased as compared with that of the characteristic curve of the emulsion containing no high molecular weight compound.
  • curling is reduced by adding to the silver halide emulsion thereof naturally occurring or synthetic high styrene-and an acrylic ester may be added.
  • the curling of a photographic light-sensitive element can be reduced by adding a naturally oc- V curring or synthetic high molecular weight compound other than gelatin, such as polyvinyl acetate and av copolymer of butyl acrylate and acrylonitrile, to the undercoating layer. (See French'latent 1,308,399 and GermanPatent 1,081,755).
  • the primary object of this invention is to provide a photographic light-sensitive element having low curling characteristics.
  • a Subsidiary objects of this invention are to provide a 1 photographic light-sensitive silver halide emulsion having'improved sensitivity, maximum density, and contrast.
  • FIG. 1 is a graph illustrating the improved characteristics obtained with my invention.
  • FIG. 2 is a schematical representation of various curling values.
  • the light sensitive e'lantent comprising the emulsion layer containing the above compound has a reduced curling tendency.
  • R ca coH.-d .0 ll. 1 5 611120122 wherein R, and R, are H or CH R, is an alkyl group having one to threecarbon atoms; 1: and y are'positive wherein n is 1, 2, or 3, preferably 2.
  • invention 1 is from about 1 to about 50, with y being determined by It is preferred that the proportion of N-alkoxymethyl alkenoylamide be above 30 mol percent.
  • the copolymers may be used singly or as mixturesthereof. If the polymerization degree of the copolymer is too high, the compatibility thereof with gelatin will bereduced, and hence it isdesirable that the intrinsic viscosity of the copolymer in methanol be less than about 20 at 35C.
  • any desired amount of the copolymer may be incorporated in the'emul'sion in this invention, .but the optimum amount thereof forincreasing the sensitivity, gamma value and the maximum density is influenced by the type of photographic silver halide emulsion to be adopted, as well as the use to be made of the product.
  • the proportion of the copolymer containing N-alkoxymethylalkenoylamide may be 340 percent by weight;
  • the curling tendency of a photographic light-sensitive element containing the copolymer is influenced by the kind of support and the thickness of coating, but is generally 3-50 percent by weight.
  • l30 percent by weight based on the whole medium of a photographic gelatino silver halide emulsion layer and/or a subsidiary layer (protection' layer, intermediate layer, backlayer, etc.) is used 9
  • the copolymer may be added in the emulsion at any time, butis most suitably added after the second ripening, and before coating.
  • the copolymer may be added in the emulsion as a powder, but it is convenient to add it as a 10-20 percent aqueous solution thereof.
  • the present invention is applicable to any kind of silver halide emulsions, such as asilver iodo-bromide emulsion, a silver chloro-bromide emulsion, and the like.
  • the emulsion may be sensitized preliminary with a sulfur and/or a gold compound, and may contain an optical sensitizer, a polyalkyleneoxide type sensitizer, various stabilizers, a hardening agent, a coating aid, a coupler, etc.
  • SYNTHESIS 4 calculated N Synthesis of N-Methoxymethylmethacrylamide By the same procedure as in Synthesis 1 using a mixture of 115 g; (1 mol) of N-methylolmethacrylamide, 500 ml. of methanol and 3.5 ml. of concentrated hydrochloric acid, 103 g. (yield percent) of a colorless liquid having a boiling point of 8385 C/l mm.
  • EXAMPLE 2 A silver iodo-bromide emulsion which was the same as in Example 1 was mixed with a copolymer ([1 intrinsic viscosity in methanol*at' 5 was repeated using the thus prepared emulsions.
  • the copolymer [1 intrinsic viscosity in methanol*at' 5 was repeated using the thus prepared emulsions.
  • N-Methyl-p-aminophenol sulfate 4 Sodium su fite (anhydrous) 66g. Sodium carbonate (mono-hydrate) 53g. Potassium bromide 3 Hydroquinone 13g. Water to make 1 liter.
  • an emulsion containing no polymer of this invention was prepared and applied to a photographic paper by the same conditions to provide a control photographic printing paper.
  • the resulting emulsion/solution was coated onto a paper base (document paper used for quick copying; weight 85glm to an Ag amount of 27 glcm (i.e. the coating thickness) and the base was dried.
  • the same base was used with each copolymer. This base was cut into a disc having a cm diameter, and the curling value was measured.
  • the method of determination of the curling value was as follows:
  • the diameter of the disc is 10.0 cm.
  • the curling value is defined as the minimum distance between peripheries on the opposite sides of the curled disc.
  • curling was measured after the discs were cut from the specimens (dried at 50C for 72 hours) and exposed to percent relative humidity at 20C for 24 hours.
  • a light-sensitive photographic material illustrating a reduced curling tendency comprising a support, at least one photographic silver halide emulsion layer and at least one subsidiary layer, at least one of said emulsion layer and subsidiary layer containing one member Compound VI: Saleck Pat. (U.S.P. 3,408,199) poly- (U.S.P. 3,408,199)
  • R and R each represents a member selected from the group consisting of H and CH R, represents an alkyl group having one to three carbon atoms, 1: and y represent positive integers, and Z represents a member selected from the group consisting of wherein n is l to 3.
  • I copolymer is a silver halide emulsion layer and wherein Cfiz ⁇ CO Hr-- H2 10.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US00188701A 1965-06-01 1971-09-30 Photographic light sensitive material containing copolymer layer Expired - Lifetime US3713829A (en)

Applications Claiming Priority (1)

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JP3203265 1965-06-01

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US3713829A true US3713829A (en) 1973-01-30

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US (1) US3713829A (cs)
BE (1) BE681697A (cs)
DE (1) DE1547839C3 (cs)
GB (1) GB1101409A (cs)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3957492A (en) * 1973-01-08 1976-05-18 Fuji Photo Film Co., Ltd. Photographic silver halide emulsion comprising an amphoteric copolymer
US4123277A (en) * 1973-08-21 1978-10-31 Fuji Photo Film Co., Ltd. Copolymer subbing material for photographic elements
US4513080A (en) * 1982-05-06 1985-04-23 Agfa-Gevaert Ag Photographic silver halide containing recording material with crosslinked microgel particles
US4770989A (en) * 1983-06-13 1988-09-13 Konishiroku Photo Industry Co., Ltd. Heat-developable color photosensitive element

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE790872A (nl) * 1971-11-08 1973-05-03 Agfa Gevaert Nv Ontwikkelbehandeling van fotografische zilverhalogenidematerialen bij hoge temperaturen
US4134916A (en) * 1978-02-06 1979-01-16 Texaco Development Corp. N-polyalkoxyalkyl acrylamides or methacrylamides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3341332A (en) * 1963-07-24 1967-09-12 Fuji Photo Film Co Ltd Light-sensitive photographic material containing polyalkenoylmorpholine
US3360373A (en) * 1962-12-04 1967-12-26 Ciba Ltd Process for the manufacture of silver halide emulsions by the flocculation method
US3408199A (en) * 1964-07-04 1968-10-29 Agfa Gevaert Ag Photographic material with improved silver covering power

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3360373A (en) * 1962-12-04 1967-12-26 Ciba Ltd Process for the manufacture of silver halide emulsions by the flocculation method
US3341332A (en) * 1963-07-24 1967-09-12 Fuji Photo Film Co Ltd Light-sensitive photographic material containing polyalkenoylmorpholine
US3408199A (en) * 1964-07-04 1968-10-29 Agfa Gevaert Ag Photographic material with improved silver covering power

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3957492A (en) * 1973-01-08 1976-05-18 Fuji Photo Film Co., Ltd. Photographic silver halide emulsion comprising an amphoteric copolymer
US4123277A (en) * 1973-08-21 1978-10-31 Fuji Photo Film Co., Ltd. Copolymer subbing material for photographic elements
US4513080A (en) * 1982-05-06 1985-04-23 Agfa-Gevaert Ag Photographic silver halide containing recording material with crosslinked microgel particles
US4770989A (en) * 1983-06-13 1988-09-13 Konishiroku Photo Industry Co., Ltd. Heat-developable color photosensitive element

Also Published As

Publication number Publication date
GB1101409A (en) 1968-01-31
DE1547839A1 (de) 1969-12-04
DE1547839C3 (de) 1980-09-11
BE681697A (cs) 1966-10-31
DE1547839B2 (de) 1980-01-10

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