US3682640A - Spectrally sensitized photographic materials suitable for silver dye bleaching method - Google Patents

Spectrally sensitized photographic materials suitable for silver dye bleaching method Download PDF

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Publication number
US3682640A
US3682640A US65713A US3682640DA US3682640A US 3682640 A US3682640 A US 3682640A US 65713 A US65713 A US 65713A US 3682640D A US3682640D A US 3682640DA US 3682640 A US3682640 A US 3682640A
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United States
Prior art keywords
group
dye
silver
bleaching method
emulsion
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Expired - Lifetime
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US65713A
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English (en)
Inventor
Keisuke Shiba
Masanao Hinata
Makoto Yoshida
Shinich Imai
Akira Sato
Shigaru Watanabe
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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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
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/28—Silver dye bleach processes; Materials therefor; Preparing or processing such materials
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
    • C09B23/0016—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a halogen atom
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0075—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/105—The polymethine chain containing an even number of >CH- groups two >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
    • 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
    • G03C1/22—Methine and polymethine dyes with an even number of CH groups

Definitions

  • This invention relates to the spectral sensitization of a photographic light-sensitive layer containing a dye suitable for the silver-dye bleaching method.
  • a multi-layer material having three or more component color layers differing in sensitivity to the spectrum regions is advantageous to obtain a multicolored photograph as in the case of the color developing method of the color forming type using a multi-layer photographic material.
  • a multi-layer photographic material has on a support member a redsensitive layer containing a cyan dye, a green sensitive layer containing a magenta dye, a yellow filter layer capable of decreasing the intrinsic sensitivity of the layers 3,682,640 Patented Aug. 8, 1972 ice under the filter layer and a blue-sensitive layer containing a yellow dye as an uppermost layer.
  • One of the disadvantages of the silver-dye bleaching method is that the light-sensitive speed of a dyed photographic layer is considerably decreased, because the maximum wavelength of the sensitivity substantially coincides with the absorption maximum wavelength of the dye.
  • the sensitivity of the light-sensitive layer in the silver-dye bleaching method is lower than that of other color photographic methods. Therefore, one of the great disadvantages of the silver-dye bleaching method is to prepare a layer having sufiicient sensitivity.
  • a sensitizing dye is added to the silver halide to enlarge the spectrum region of the sensitivity of the silver halide emulsion and for optical sensitization.
  • a sensitizing dye used in the lightsensitive material for the silver-dye bleaching method must satisfy certain necessary conditions.
  • the sensitizing dye should not have an adverse influence upon the sensitivity and stability of the emulsion, in particular, during storage.
  • the sensitizing dye should not cause any coloration remaining after processing of the photographic material.
  • the sensitizing dye should be adsorbed strongly on the silver halide grains so as not to be substituted by a dye suitable for the silver-dye bleaching method. Otherwise the sensitizing action is decreased by the presence of the dye suitable for the silverdye bleaching method.
  • Many of the sensitizing dyes used hitherto in silver halide materials are not suitable for the silver-dye bleaching method.
  • basic cyanines tend to be desorbed from silver halide grains by a dye having sulfonate group, suitable for the silver-dye bleaching method.
  • Betaine cyanines may be used as sensitizing dyes for a photographic layer in the silver-dye bleaching method, but often retain a slight coloring therein.
  • a photographic light-sensitive layer suitable for the silver-dye bleaching method and having an extraordinarily high sensitivity is prepared by adding to a silver halide emulsion containing a dye suitable for the silver dye bleaching method, a sensitizing dye represented by the following general Formula I, as a sensitizer.
  • R represents an alkyl, a substituted alkyl, an aryl, an aralkyl, or an allyl group
  • R and R each represents a hydrogen atom, an alkyl, a substituted alkyl, an allyl, an aralkyl, a substituted aralkyl and an aryl group
  • R represents a hydrogen atom, an alkyl or an aryl group
  • Z represents the non-metallic atoms necessary to complete a 5- or G-membe'red heterocyclic ring
  • d represents 0, 1 or 2
  • n represents 1 or 2.
  • R in the general Formula I can be, for example, a methyl, an ethyl, a propyl, a ,B-hydroxyethyl, a B-acetoxyethyl, a sulfatoethyl, a carboxymethyl, a B-carboxyethyl, a y-carboxypropyl, a ,B-sulfoethyl, a 'y-sulfopropyl, a 6- sulfobutyl, a vinylmethyl, a benzyl, a p-carboxybenzyl, a p-sulfophenethyl or a phenyl group.
  • R and R in the general Formula I can be, for example, a methyl, an ethyl, a propyl, a fl-hydroxyethyl, a ,3- acetoxyethyl, a sulfatoethyl, a carboxymethyl, a ,B-carboxyethyl, a 'y-carboxypropyl, a fl-sulfoethyl, a -sulfopropyl, a a-sulfobutyl, a vinylmethyl, a benzyl, a phenyl, a p-carboxybenzyl, and a p-sulfophenethyl group.
  • R in the general Formula I can be, for example, a hydrogen atom, a methyl, an ethyl or a phenyl group.
  • Suitable examples of the heterocyclic ring containing Z in the general Formula I are thiazoles, such as thiazole and thiazoles having a methyl or aphenyl group in the ring; benzothiazoles, such as benbothiazole and benzothiazoles having nucleus substituents such as a halogen atom, alkyl, alkoxy and phenyl groups in the benzene ring; naphthothiazoles, such as a-naphthothiazole, B-naphthothiazole, tetrahydronaphthothiazole and napht-hothiazoles having nucleus substituents such as an alkoxy group in any of the benzene rings; oxazoles, such as oxazole and oxazoles having substituents such as alkyl and phenyl groups in the ring; benzoxazoles, such as benzoxazole and benzoxazoles having nu
  • the sensitizing dye represented by the general Formula I is a dye having four hetero radicals wherein two ketomethylene radicals are directly bonded.
  • the sensitizing dye can sensitize a silver halide emulsion strongly in coexistence with the dye used in the silver-dye bleaching method. 'Since the dye gives a more excellent sensitivity even in the case of a small quantity of the dye added per g-mole of the silver halide in comparison with conventional basic cyanine dyes, any photographic layer containing the dye substantially is freed from any color remaining after processing.
  • the sensitizing dye represented by the general Formula I can favorably sensitize an emulsion used in the silverdye bleaching method, containing a dye suitable for the silver-dye bleaching method, without any aid, but the supersensitization thereof by a compound represented by the following general Formula II or III is preferred.
  • R R R and R each represents a hydrogen atom, a hydroxyl group, an alkoxy! group, an aryloxyl group, a substituted aryloxyl group such as phenoxyl, o-toloxyl or p-sulfophenoxyl group, a halogen atom such as a chlorine or a bromine atom, a heterocyclic nucleus such as morpholinyl or pipcridyl, an alkylthio group such as a methylthio or an ethylthio group, a heterocyclic thio group such as a benzothiazylthio group, an arylthio group such as a phenylthio or a tolylthio group, an amino group, an alkylamino group or a substituted alkylamino group such as a methylamino, an ethylamino, a propylamin
  • A is:
  • R represents an acylamino group such as an acetamide, a sulfobenzamide, a 4-methoxy-3-sulfobenzamide, a Z-ethoxybenzamide, a 2,4 diethoxybenzamide, a p-toluylamino, a 4-methyl-Z-methoxybenzamide, a l-naphthylamino, a 2-naphthylamino, a 2,4-dimethoxybenzamide, a 2-phenylbenzamide, or a Z-thienylbenzamide group, or a sulfo group
  • R represents an acylamino group such as defined for R R represents a hydrogen atom or a sulfo group and the general Formula III has at least one sulfo group.
  • the sensitizing dye represented by the general Formula I is used more advantageously through supersensitization with a novolak type condensate of a polyhydroxybenzene and formaldehyde where the term polyhydroxybenzene is intended to encompass a substituted benzene having from 1 to 3 hydroxyl groups on the benzene nu cleus.
  • the novolak type condensate of the polyhydroxybenzene and formaldehyde will hereinafter be referred to as the formalin condensate.
  • the polyhydroxybenzene is represented by the following general Formulae (W21, W13, IVc, IVd,
  • ORrz S02E11 (1V0) (Oin ([V(]) 011 in which R and R each represents OH, OM, R141 NHg, NHRpg, -(R14)2, and NHNHR R represents an alkyl group of from 1 to 8 carbon atoms, an aryl group or an aralkyl group, M represents an alkali metal or an alkaline earth metal, X represents OH or a halogen atom, X represents a halogen atom, and n n n and 12* each represents 1, 2 or 3 except that n and n are equal to 3 at the same time.
  • the sensitizing dye of the invention represented by the general Formula I is described in British Pats. Nos. 487,051 and 489,335, and in US. Pat. No. 2,504,615.
  • the condensate of the polyhydroxybenzene can be synthesized according to the conventional synthesis method for phenol-formaldehyde resins of the novolak type [for example, as described in W. R. Sorenson, T. W. Campbell, Preparative Methods of Polymer Chemistry, John Wiley and Sons, Inc. (1961)].
  • the poly-substituted hydroxybenzene is dispersed in Water, heated after concentrated hydrochloric acid and 37% formalin are added and held at 100 C. for 30 minutes to 1 hour with agitation. Then, if necessary, hydrochloric acid is further added and the heating with agitation is continued. After the reaction, the reaction product is removed into cold water and the resultant precipitate can be purified.
  • the product is obtained by filtering and dried.
  • Other condensates can be obtained readily using other polyhydroxybenzenes in place of the p-hydroxybenzoic acid used in the above-described method.
  • the condensation unit (degree of polymerization) of the condensate obtained by the above-described method is from 2 to 10 as in the usual novolak resins.
  • condensates having a polymerization degree of from 2 to 10, preferably hav ing a polymerization degree of from 2 to 5 and a molecular weight of from 300 to 800 are suitable.
  • sensitizing dyes used in the invention are given as follows without limiting the invention.
  • H erably is added to an emulsion before coating, washed 01H (11H; with water, before a dye suitable for the silver dye bleaching method is added.
  • silver halides such as silver chloride, silver bromide, silver iodobromide, silver chlorobrornide or silver chloroiodobromide can be used.
  • gelatino-silver halide emulsion is used in the invention, but cellulose derivatives and resinous s 1 1 materials which do not afiect the light-sensitive materials can be used in place of gelatin.
  • the photographic emulsion used in the invention can contain conventional additives such as chemical sensi- N tizers, fog inhibitors, stabilizers, hardeners, coating aids, t plasticizers, development accelerators and air fog inhibitors.
  • the photographic emulsion can be coated onto a suit- I-11 able support such as glass, cellulose derivative films, syn- S R O thetic resin films, laminated papers or synthetic papers ZHS in conventional manner.
  • a suit- I-11 able support such as glass, cellulose derivative films, syn- S R O thetic resin films, laminated papers or synthetic papers ZHS in conventional manner.
  • the dye suitable for the silver dye bleaching method and used in combination with the sensitizing dye repres s sented by the general Formula I is a dye used conven- I tionally in the silver-dye bleaching method, preferably containing a phenolic hydroxyl group or a sulfonate group.
  • Suitable dyes are described in Japanese Patent Publications 10,280/61, 9,587/64, and 25,768/64; U.S. Pats.
  • the sensitizing dye represented by the general Formula 3,264,109, 3,454,402, 3,178,291, 3,385,706, 3,455,695, I is added to a photographic layer used in the silver-dye 3,259,498, 3,244,525, 3,304,181, 3,322,543, 3,210,190, bleaching method wth a dye suitable for the silver-dye 3,454,401, 3,211,554 and 3,223,527. Suitable examples bleaching method.
  • the sensitizing dye prefare as follows;
  • MMQMa nEt m-@-t1msn t ⁇ 0H HOG B035 3 01H I J Q Hons- S H 50H a 3 Q-CO-NH 0H H5020 with R being a benzoyl, a 4-acetylaminobenzoyl or a 4 benzoylaminobenzyl group. 50
  • EXAMPLE 1 9.68 g.-mol/g.-mol silver halide of a sensitizing dye was added to a silver chlorobromide emulsion (Br mol percent, CI mol percent) and stirred adequately for 20 minutes. 24.2 g./g.-mol silver halide of a dye represented by the following structural formula was added thereto, stirred adequately and coated onto a cellulose 60 triacetate base. The coated photographic layer was exposed through a step wedge of a blue light (Latten Filter No. 47B) and a red light (Fuji Filter N0. 7), developed and fixed. The development was carried out using the composition of Table 1 at 20 C. for 2 minutes.
  • R R and R are selected from the group consisting of methyl, ethyl, propyl, B-hydroxyethyl, fl-acetovyethyl, sulfatoethyl, carboxymethyl, p-carboxyethyl, 'y-carboxypropyl, fi-sulfoethyl, 'y-sulfopropyl, 6- sulfobutyl, vinylmethyl, benzyl, phenethyl, p-carboxybenzyl, p-sulfophenethyl and phenyl groups; and the heterocyclic ring containing Z is selected from the group consisting of the thiazoles, benzothiazoles, naphthothiazoles, oxazoles, benzoxazoles, naphthothiazoles, selenazoles, benzoselenazoles, naphthose
  • A is selected from the group consisting of A and A wherein A is selected from the group consisting of l l I $0 M M035 $0 M I l and $0 M $0 M wherein A is selected from the group consisting of and and wherein at least one of R R R and R contains a substituent containing a SO M group when A is A 4.
  • 3,682,640 16 contains additionally at least one of compound having densation unit of from 2 to 5 and a molecular weight of the following general Formula III from- 300 to 800.
  • the light-sensitive silver halide emulsion as 6.
  • Thc supefsensitiled Photographic emulsion as 13 The light-sensitive silver halide emulsion as claimed in claim 7, wherein the condensate is a novolak l i d i lai 1, wherein the dye capable of being yp condensate of formaldehyde a d a p y y ybleached out in the silver dye bleaching process is benzene selected from the group consisting of compounds having the following general formula: OH H304) OH (0B).. 1 (0H).
  • a photographic light'sensitive element comprising wherein R and R each is selected from the group a supPort thereon. least layer cqntainlng the lightconsisting of NH2, sensitive silver hahde emulsion as claimed in claim 1.
  • R14 is selected from the group consisting of an alkyl group References Cited having from 1 to 8 carbon atoms, an aryl group and UNITED STATES PATENTS an aral'kyl group, wherein M i selected from the group 2,652,330 9/1953 Carroll 96 123 consisting of an alkali metal and an alkaline earth metal, 3,401,404 9/1968 Seidel et ah wherein X is selected from the group consisting of 3,565,630 2/1971 Millikan et a1 OH and a halogen atom, wherein X: is a halogen atom, wherein n n n and n each represents 1, 2, 3 except J TRAVIS BROWN, P i E i that n and n are equal to 3 simultaneously.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Plural Heterocyclic Compounds (AREA)
US65713A 1969-08-20 1970-08-20 Spectrally sensitized photographic materials suitable for silver dye bleaching method Expired - Lifetime US3682640A (en)

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JP44065828A JPS4933785B1 (fr) 1969-08-20 1969-08-20

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US (1) US3682640A (fr)
JP (1) JPS4933785B1 (fr)
BE (1) BE755064A (fr)
CA (1) CA971817A (fr)
CH (1) CH548049A (fr)
FR (1) FR2058405B1 (fr)
GB (1) GB1325487A (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3920458A (en) * 1970-09-28 1975-11-18 Fuji Photo Film Co Ltd Photographic sensitive material suitable for the silver-dyestuff bleaching method
US5563021A (en) * 1995-03-31 1996-10-08 Eastman Kodak Company Photographic elements with tetra-nuclear merocyanine sensitizers
US5580711A (en) * 1993-03-02 1996-12-03 Konica Corporation Silver halide photographic light-sensitive material
US5679795A (en) * 1995-02-28 1997-10-21 Eastman Kodak Company Method of synthesizing dyes and precursor compounds therefor
US6022307A (en) * 1998-07-14 2000-02-08 American Cyanamid Company Substituted dibenzothiophenes having antiangiogenic activity

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE68912780T3 (de) * 1989-11-14 2006-08-03 Agfa-Gevaert N.V. Verfahren zur Herstellung eines Silberbildes
JP3041734B2 (ja) * 1991-10-29 2000-05-15 コニカ株式会社 ハロゲン化銀写真感光材料

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3920458A (en) * 1970-09-28 1975-11-18 Fuji Photo Film Co Ltd Photographic sensitive material suitable for the silver-dyestuff bleaching method
US5580711A (en) * 1993-03-02 1996-12-03 Konica Corporation Silver halide photographic light-sensitive material
US5679795A (en) * 1995-02-28 1997-10-21 Eastman Kodak Company Method of synthesizing dyes and precursor compounds therefor
US5563021A (en) * 1995-03-31 1996-10-08 Eastman Kodak Company Photographic elements with tetra-nuclear merocyanine sensitizers
US6022307A (en) * 1998-07-14 2000-02-08 American Cyanamid Company Substituted dibenzothiophenes having antiangiogenic activity

Also Published As

Publication number Publication date
FR2058405B1 (fr) 1973-01-12
DE2041200B2 (de) 1976-04-29
CA971817A (en) 1975-07-29
GB1325487A (en) 1973-08-01
JPS4933785B1 (fr) 1974-09-10
DE2041200A1 (de) 1971-11-18
FR2058405A1 (fr) 1971-05-28
BE755064A (fr) 1971-02-01
CH548049A (de) 1974-04-11

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