US3922170A - Spectrally sensitized silver halide photographic emulsion - Google Patents

Spectrally sensitized silver halide photographic emulsion Download PDF

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Publication number
US3922170A
US3922170A US381137A US38113773A US3922170A US 3922170 A US3922170 A US 3922170A US 381137 A US381137 A US 381137A US 38113773 A US38113773 A US 38113773A US 3922170 A US3922170 A US 3922170A
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group
benzoxazole
silver halide
radical
ring
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US381137A
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Keisuke Shiba
Akira Sato
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Fujifilm Holdings Corp
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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
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/28—Sensitivity-increasing substances together with supersensitising substances
    • G03C1/29—Sensitivity-increasing substances together with supersensitising substances the supersensitising mixture being solely composed of dyes ; Combination of dyes, even if the supersensitising effect is not explicitly disclosed
    • 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
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
    • 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
    • C09B23/12—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being branched "branched" means that the substituent on the polymethine chain forms a new conjugated system, e.g. most trinuclear cyanine dyes

Definitions

  • ABSTRACT A silver halide photographic emulsion which is spectrally sensitized so that it has a maximum sensitivity wave length within the region of 580 nm 640 nm. characterized by containing in a super sensitizing amount the combination of at least one carbocyanine dye represented by the general formula (1) and at least one of the dyes selected from the group consisting of dyes represented by the general formula (11) and (111):
  • Z represents the grouping necessary for the formation of B-naphthothiazole or B-naphthoselenazole ring.
  • Z represents the grouping necessary for the formation of henzoxazole ring.
  • A represents a hydrogen atom. an alkyl radical or an aryl radical.
  • R and R each represents an alkyl radical. at least one o1 which represents a hydroxyalkyl radical. a carbosyalkyl radical or alkyl radical having a sull'o group X. represents an acid anion group. and l is l. or Z the dye forming an intramolecular salt when l is l:
  • Z and Z each represents the grouping necessary for the formation of a benzothiazole.
  • A; represents a hydrogen atom. an alkyl radical having less than three carbon atoms or an aryl radical.
  • R and R each represents an alkyl radical. at least one oi which represents a hydroxyalkyl radical. a carbosyal kyl radical or an alkyl radical having a sulto group.
  • X;- represents an acid anion group. and m is l or Z.
  • Z represents the grouping necessary for the formation of a benzoxazole orbenzimidazole ring.
  • Z represents the grouping necessary for the formation of a benzothiazole, benzoselenazole or B-naphthothiazole ring
  • A represents a hydrogen atom. an alkyl radical having less than three carbon atoms or an aryl radical.
  • R and R each represents an alkyl radical. at least one of which represents a hydroxyalkyl radical. a carboxyalkyl radical or an alkyl radical having a sulfo group.
  • X represents an acid anion group.
  • n is l. the dye forming an intramolecular salt when n is 1.
  • FIG 9 FIG. IO
  • the present invention relates to a silver halide photographic emulsion in which a specific wave length range is highly spectrally sensitized by a supersensitization, more especially, the present invention relates to a sliver halide photographic emulsion in which the wave length range from 580 nm to 640 nm is spectrally sensitized,
  • a first object of the present invention is to provide a new supersensitization technique to selectively increase the sensitivity within the wave length region from about 580 nm to 640 nm.
  • Another object of the present invention is to diminish the color residue which typically remains after development.
  • a further object of the present invention is to provide a sensitizing dye that does not diffuse into and sensitize adjacent sensitive layers when a layer ofa multi layer sensitive material is selectively spectrally sensitized.
  • Z represents the grouping necessary for the formation of a B-naphthothiazole or B-naphthoselenazole ring
  • Z represents the grouping necessary for the formation of a benzoxazole ring
  • A represents hydrogen atom, an alkyl group, (e.g., an unsubstituted alkyl group having up to 4 carbon atoms or a monoaralkyl group wherein the alkyl moiety has up to 2 4 carbon atoms) or monoaryl (ie. unsubstituted or sub stituted monoaryl) radical
  • R and R each represents an alkyl (i.e.
  • A represents a hydrogen atom.
  • an alkyl radical having less than three carbon atoms or a monoaryl radical i.e., unsubstituted or substituted monoaryl R and R each represents an alkyl (ie an unsubstituted alkyl group preferably having up to 8 carbon atoms and a substituted alkyl group wherein the alkyl moiety preferably has up to 4 carbon atoms) radical. at least one of which is a hydroxyalkyl, carboxyalkyl or alkyl radical having a sulfo group, X- ⁇ is an acid anion group. and m is 1 or 2, being l when the dye forms an intramolecular salt (similar to a betaine structure).
  • Z represents the grouping necessary for the formation of a benzoxazole or benzimidazole ring
  • Z represents the grouping necessary for the formation of a benzothiazole, benzoselenazole or B-naphthothiazole ring
  • A represents a hydrogen atom, an alkyl group (e.g. an unsubstituted alkyl group having up to 4 carbon atoms and a monoaralkyl group wherein the alkyl moiety has up to 4 carbon atoms) or a monoaryl (i.e. unsubstituted or substituted monoaryl) radical.
  • R and R each represents an alkyl (ie.
  • FIGS. 1 15 are characteristic curves of dyes employed as described in the Examples given hereafter.
  • FIG. 16 is the spectral transmittance curve of an SP- l-filter and FIG. I7 shows the spectral transmittance of filters SC-SO & SC56.
  • the preferred silver halides are silver iododuCIiOn sensitized N 2.
  • l bromide A preferred halogen composition by mole 7r 2,419,974. 2,983,6[0 etc.) or sensitized by a combinaof iodine is no greater than l0 mol "/c, for example, tion of the methods mentioned above. from 2 to 7 mol "1? iodine.) or chloroidobromide (A
  • the photographic emulsion according to this inven preferred halogen composition by mo] 92 ofiodine is no 60 tion may contain as a chemical sensitizer a sulfur sensigreater than 5 mol /2.
  • tizer such as allyl thiocarbamide, thiourea,sodium thioiodine.
  • the bromine or chlorine composition is up sulfate and cysteine; a noble metal sensitizer such as tional.
  • the average diameter of the silver halide partipotassium chloroaurate, aurous thiosulfate and potascles is not limited but preferably is 0.04 2 (arithmetisium chloropalladate; a reducing sensitizer such as tin cal mean determined by, for example, the proje t d chloridephenyl hydrazine and reductone,and the like. area method).
  • the silver halide photographic emulsion used in this fine COmPOUIIdS h H5 "1056 diSClOSed i HI- N invention can be physically and chemically sensitized in 2,716,062, polyoxypropylene compounds and compounds having quaternary ammomium group such as those disclosed in U.S. Pat. Nos. 2,271,623; 2,334,864; 2,288,226 and the like.
  • the photographic emulsion may contain anti-fogging agents such as nitrobenzimidazole and ammonium chloroplatinate and stabilizers such as 4-hydroxy-6-methyl-l ,3,3a,7-tetrazaindene.
  • the photographic emulsion may also contain hardening agents such as formaldehyde. chrome alum, l-hydroxy-3,S-dichlorotriazine soda, glyoxal and dichloroacrolein; and coating assistants such as saponin and sodium alkylbenzene sulfonates.
  • hardening agents such as formaldehyde. chrome alum, l-hydroxy-3,S-dichlorotriazine soda, glyoxal and dichloroacrolein
  • coating assistants such as saponin and sodium alkylbenzene sulfonates.
  • the silver halide emulsion used in this invention may contain color couplers and dispersing agents therefor.
  • color couplers especially cyan coupler are present.
  • couplers of the phenol series as described in U.S. Pat. No. 2,698,794 or couplers of the naphthol series are described in U.S. Pat. No. 2,474,293 are especially useful.
  • the silver halide photographic emulsion used in this invention can be based upon protective colloids other than gelatin, for example, gelatin derivatives such as phthalated or malonated gelatin; cellulose derivatives such as hydroxyethyl or carboxymethyl cellulose; soluble starches such as dextrin; hydrophilic polymers such as polyvinyl alcohol, polyvinyl pyrrolidone, polyacryiamide and polystyrene sulfonic acid; plasticizers for dimensional stability; latex polymers and matting agents.
  • the generally used ratio by weight of silver halide to the binder is from about 1:4 to 4:1.
  • the finished emulsion is coated on any suitable support, for example, baryta paper, resin-coated paper, synthetic paper, triacetate film, polyethylene terephthalate film, glass plate and other plastic bases.
  • the sensitizing dyes used in this invention can be added to the emulsion as a solution in water or a watermiscible organic solvent such as methanol, ethanol, methyl cellosolve, pyridine and the like.
  • the amount of the dyes added is as is commonly used for the supersensitization, e.g. about 55 X l X 10 mol of dye per mol of silver, and the ratio of the dye or dyes of general formula (11) and/or (III) to the dye or dyes of the general formula (I) is preferably about 1:100-121 (mol ratio). It is especially preferred that the amount of dye or dyes of general formula (1) be larger than that of the dye of general formula (11) (mol ratio).
  • the dyes used in this invention can be used for spectral sensitization according to the method described in German Laid Open Specification 2,104,283 and in U.S. Pat. No. 3,649,286.
  • EXAMPLE 1 Silver halide particles were precipitated in a gelatin binder by the double jet method, physically aged in a common manner, subjected to desalting treatment and chemically aged with 4 ml of an aqueous solution con taining hypo and having a concentration of l by weight and 10 ml ofan aqueous solution containing potassium chloroaurate and having a concentration of 1 71 by weight so that a silver iodobromide (iodine content: 6 mol7r) emulsion was manufactured.
  • the emulsion contained 0.6 mol of silver halide/kg of emulsion.
  • the grain size of the silver halide formed was 0.8a.
  • One kg of emulsion was placed in a crucible and dissolved in a constant temperature bath at 50C.
  • aqueous solution of lhydroxy-3,S-dichlorotriazine soda and 10 cc of a l wt.% aqueous solution of sodium dodecyl benzene sulfonate were added thereto and the system stirred.
  • the resulting finished emulsion was coated on a cellulose triacetate film base to a dried film thickness of 5 microns, and dried to yield a sample of a sensitive ma terial.
  • the film sample was cut into strips.
  • One strip was ex posed with an optical wedge to a light source provided with a blue filter (SP 1 a yellow filter (SC-50 and a red filter (SC-56) (all by Fuji Photo Film Co., Ltd.) using a sensitometer having a 5,400K color tempera ture light source.
  • SP 1 a blue filter
  • SC-50 and a red filter (SC-56) all by Fuji Photo Film Co., Ltd.
  • the remaining strips were exposed to obtain spectrograms using a diffraction grating spectrograph having a 2,666K tungsten light source.
  • the exposed strips were developed with a liquid developer having the following composition at 20C for 2 minutes, stopped, fixed and washed with water to yield strips having a black-and-white image.
  • the densities of these strips were determined by an S-type densitometer (Fuji Photo Film Co., Ltd.) to measure the blue filter sensitivity (Sb), the yellow filter sensitivity (Sy), the red filter sensitivity (Sr) and fog.
  • the base value of optical density for determining sensitivity was (fog 0.20).
  • the spectral transmittance curve of the SP-l filter is shown in FIG. 16 and those of the SC-SO and SC56 filters in FIG. 17.
  • the resulting spectrograms are shown in FIG. 145.
  • FIG 2 32 79 85 0.06
  • FIG 2 4 IIA) 4 (IIC) l I05 IIO 96 0.09
  • FIG. 5 I0 (IA) 4 (IIIA) I II7 II7 76 0.10
  • FIG.5 II 6 III I) 2 56 63 I00 0.07
  • FIG. 7 I6 Ii (III B] I 63 25 I05 006 2 I00 I00 0.06
  • FIG. 8 I8 9 (IC) 2 I4I I26 87 0.07
  • FIG. 9 2
  • the combinations of sensitizing dyes having a supersensitization effect according to this invention are useful for the spectral sensitization of silver halide emulsions in the red sensitive layer of color sensitive material such as color negative and reversal sensitive materials, the spectral sensitization of silver halide emulsions used for black-and-white sensitive materials, the spectral sensitization of silver halides used as a printing plate sensitive material and the spectral sensitization of 50 cording to this invention in order to render practically the green sensitivity less than the red sensitivity obtained by this invention.
  • dyes are used are described in Japanese Patent Publications Nos. 18459/66, 3504/68. I3l68/68 and 22069164; Japanese Pat. applications Nos. 98474/71, 42668/7] and 42667]? I and US. Pat. Nos. 3,440,051,
  • a color sensitive material comprising an emulsion containing a cyan coupler, characterized by containing in a supersensitizing amount the combination of at least one carbocyanine dye represented by general formula (I) and at least one dye selected from the group consisting of dyes represented by general formula (II) and (11]).
  • a silver halide photographic emulsion which is spectrally sensitized so that it has a maximum sensitiv ity wave length within the region of 580 nm 640 nm, characterized by containing in a supersensitizing amount the combination of:
  • Z represents the grouping necessary for the formation of B-naphthothiazole or B-naphthoselenazole ring
  • Z represents the grouping necessary for the formation of benzoxazole ring
  • A represents a hydrogen atom, an alkyl radical, or an aryl radical
  • R represents an alkyl radical, at least one of which represents a hydroxyalkyl radical, a carboxyalkyl radical or alkyl radical having a sulfo group
  • x represents an acid anion group, and 1 is l or 2, the dye forming an intramolecular salt when I is l:
  • Z represents the grouping necessary for the formation of a benzoxazole or benzimidazole ring
  • 2, represents the grouping necessary for the formation of a benzothiazole, benzosclenazole or B-naphthothiazole ring, when 2,, is a benzimidazole ring and 2,, represents the grouping necessary for the formation of a bcnzothi azole or benzoselenazole ring when Z is a benzoxazole ring
  • A represents a hydrogen atom. an alkyl radical having less than three carbon atoms or an aryl radical.
  • R and R each represents an alkyl radical, at least one of which represents a hydroxyalkyl radical. a carboxyalkyl radical or an alkyl radical having a sulfo group
  • X represents an acid anion group
  • n is l, the dye forming an mtramolecular salt when n is l
  • said substituent being selected from the group consisting of an alkyl group, a halogen atom, a monoaryl group, an alkoxy group, a hydroxy group, an alkoxy carbonyl group, a cyano group, an amino group, an aminocarbonyl group, a monoaryloxy group and an acyl group.
  • Z is a benzoxazole.
  • A, and A each is a hydrogen atom, a methyl, ethyl. propyl. phenethyl or phenyl radical; wherein R,, R R and R each is a methyl. ethyl, propyl, allyl, 2-carboxyethyl.
  • Z is a ring as described for Z or 5-chlorobenzimidazole, 5,-dichlorobenzimidazole.
  • X,, and X each represents an iodine, bromine, chlorine, p-toluene sulfonic acid, benzene sulfonic acid, ethyl sulfate, perchlorate, or rhodan ions.
  • the silver halide photographic emulsion of claim I wherein said dye of the general formula (I) is Se CH l l c P- N/ (2H5 llllC) (lllDl 5.
  • said dyes of the general formula (I), and (III) are present at a level of from about 5 X to l X 10 mol of dye per mol of silver and wherein the molar ratio of the amount of dye of the general formula (ll) and (III) to the amount of dye of the general formula (l) is about l:100 to lzl.
  • Z is a ,B-naphthothiazole ring
  • Z is a benz oxazole ring which is substituted at the 5-position with a chlorine atom. a trifluoromethyl group, a methyl group or a phenyl group and A is an ethyl group.
  • a silver halide photographic material comprising a support having thereon the silver halide emulsion ol claim I.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
US381137A 1972-07-20 1973-07-20 Spectrally sensitized silver halide photographic emulsion Expired - Lifetime US3922170A (en)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3977882A (en) * 1972-07-20 1976-08-31 Fuji Photo Film Co., Ltd. Spectrally sensitized silver halide photographic emulsion
US4039335A (en) * 1975-10-29 1977-08-02 Fuji Photo Film Co., Ltd. Photographic silver halide emulsions
US4135933A (en) * 1975-06-20 1979-01-23 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
US4147553A (en) * 1977-02-10 1979-04-03 Fuji Photo Film Co., Ltd. Supersensitized photographic emulsion
US4307185A (en) * 1975-09-09 1981-12-22 Fuji Photo Film Co., Ltd. Photographic silver halide emulsions
US4308345A (en) * 1975-10-09 1981-12-29 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
US4326023A (en) * 1976-09-15 1982-04-20 Eastman Kodak Company Spectral sensitization of photographic emulsions
US5723280A (en) * 1995-11-13 1998-03-03 Eastman Kodak Company Photographic element comprising a red sensitive silver halide emulsion layer
US5853968A (en) * 1996-11-27 1998-12-29 Eastman Kodak Company Multilayer color photographic element

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58168240A (ja) * 1982-03-30 1983-10-04 Fujitsu Ltd 半導体装置

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3177210A (en) * 1962-11-29 1965-04-06 Polaroid Corp Process for preparing cyanine spectral sensitizing dyes
US3338714A (en) * 1963-08-26 1967-08-29 Ilford Ltd Photographic supersensitized silver halide emulsions
US3463640A (en) * 1964-12-17 1969-08-26 Ilford Ltd Supersensitised silver halide emulsions with three cyanine dyes
US3615609A (en) * 1965-09-23 1971-10-26 Ilford Ltd Supersensitising dyes
US3679428A (en) * 1969-07-23 1972-07-25 Fuji Photo Film Co Ltd Spectrally sensitized photographic emulsions
US3711288A (en) * 1966-07-28 1973-01-16 Konishiroku Photo Ind Light-sensitive,photographic silver halide emulsion

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1113873B (de) * 1959-01-17 1961-09-14 Wolfen Filmfab Veb Verfahren zur Sensibilisierung von Halogensilberemulsionen

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3177210A (en) * 1962-11-29 1965-04-06 Polaroid Corp Process for preparing cyanine spectral sensitizing dyes
US3338714A (en) * 1963-08-26 1967-08-29 Ilford Ltd Photographic supersensitized silver halide emulsions
US3463640A (en) * 1964-12-17 1969-08-26 Ilford Ltd Supersensitised silver halide emulsions with three cyanine dyes
US3615609A (en) * 1965-09-23 1971-10-26 Ilford Ltd Supersensitising dyes
US3711288A (en) * 1966-07-28 1973-01-16 Konishiroku Photo Ind Light-sensitive,photographic silver halide emulsion
US3679428A (en) * 1969-07-23 1972-07-25 Fuji Photo Film Co Ltd Spectrally sensitized photographic emulsions

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3977882A (en) * 1972-07-20 1976-08-31 Fuji Photo Film Co., Ltd. Spectrally sensitized silver halide photographic emulsion
US4135933A (en) * 1975-06-20 1979-01-23 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
US4307185A (en) * 1975-09-09 1981-12-22 Fuji Photo Film Co., Ltd. Photographic silver halide emulsions
US4308345A (en) * 1975-10-09 1981-12-29 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
US4039335A (en) * 1975-10-29 1977-08-02 Fuji Photo Film Co., Ltd. Photographic silver halide emulsions
US4326023A (en) * 1976-09-15 1982-04-20 Eastman Kodak Company Spectral sensitization of photographic emulsions
US4147553A (en) * 1977-02-10 1979-04-03 Fuji Photo Film Co., Ltd. Supersensitized photographic emulsion
US5723280A (en) * 1995-11-13 1998-03-03 Eastman Kodak Company Photographic element comprising a red sensitive silver halide emulsion layer
US5853968A (en) * 1996-11-27 1998-12-29 Eastman Kodak Company Multilayer color photographic element

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GB1434798A (en) 1976-05-05
JPS5544368B2 (US20110105765A1-20110505-C00013.png) 1980-11-12
FR2193991B1 (US20110105765A1-20110505-C00013.png) 1977-12-23
FR2193991A1 (US20110105765A1-20110505-C00013.png) 1974-02-22
JPS4932634A (US20110105765A1-20110505-C00013.png) 1974-03-25

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