US2735766A - Prevention of dye wandering in - Google Patents

Prevention of dye wandering in Download PDF

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US2735766A
US2735766A US2735766DA US2735766A US 2735766 A US2735766 A US 2735766A US 2735766D A US2735766D A US 2735766DA US 2735766 A US2735766 A US 2735766A
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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
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes
    • G03C1/22—Methine and polymethine dyes with an even number of 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
    • G03C1/035—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein characterised by the crystal form or composition, e.g. mixed grain
    • 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
    • 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
    • G03C1/035—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein characterised by the crystal form or composition, e.g. mixed grain
    • G03C2001/03564—Mixed grains or mixture of emulsions
    • 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
    • G03C2200/00—Details
    • G03C2200/06—Additive

Definitions

  • This invention relates to photographic silver halide emulsions and more particularly to-photographic silver halide emulsions sensitized with certain optical sensitizing dyes.
  • sensitizing dyes the type depending upon the ultimate purpose of the photographic material.
  • One serious drawback in the use of such optical sensitizing dyes has been their tendency to wander from the emulsion in which they have been incorporated in certain instances. This objection is particularly noticeable in the preparation of mutlilayer photographic materials, or in the preparation of photographic materials giving various degrees of contrast. In these instances, the optical sensitizing dyes have a tendency to migrate from the emulsion in which they have been incorporated into a second emulsion in which their presence is undesirable.
  • an object of my invention to provide a method of preventing dye wandering in photographic silver halide emulsions. Another object is to provide a photographic material giving various degrees of contrast, wherein the tendency toward dye wandering is eliminated or materially reduced. Other objects will become apparent from a consideration of the following description and examples.
  • n-propyl, S-hydroxyethyl, etc. (e. g. an alkyl group of from 1 to 2 carbon atoms)
  • L represents a methine' group
  • d represents a positive integer of from 1 to 3
  • n represents a positive integer of from 1 to 2
  • 2' represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing from 5 to 6 atoms in the heter0-' "ice droxybenzothiazole, 6-hydroxybenzothiaz0le, etc.), those of the naphthothiazole series (e. g.
  • benzoxazole 5-chlorobenzoxazole, 5-phenylbenzoxazole, S-methylbenzoxazole, 6-methylbenzoxazole, 5,6-dimethylbenzoxazole, 4,6-dimethylbenzoxazole, 5-methoxybenzoxazole, 6-methoxybenzoxazole, S-ethoxybenzoxazole, 6-chlorobenzoxazole, 5-hydr0xybenzoxazole, 6-hydroxybenzoxazole, etc.), those of the naphthoxazole series (e. g. a-naphthoxazole, fi-naphthoxazole, etc.), those of the selenazole series (e. g.
  • 4-quinoline series e. g. quinoline, 6-methoxyquinoline, 7-methylquinoline, S-methylquinoline, etc.
  • 3,3 -dialkylindolenine series e. g. 3,3 -dimethylindolenine, 3,3,5 trimethylindolenine, 3,3,7 trimethylindolenine, etc.
  • Z-pyridine series e. g.
  • pyridine 3-methylpyridine, 4-methylpyridine, S-methylpyridine, 6- methylpyridine, 3,4-dimethylpyridine, 3,5-dirnethylpyridine, 3,6-dimethylpyridine, 4,5-dimethylpyridine, 4,6-dimethylpyridine, 4-chloropyridine, 5-chloropyridine, 6- chloropyridine, 3-hydroxypyridine, 4-hydroxypyridine, 5- hydroxypyridine, 6-hydroxypyridine, 3-phenylpyridine, 4- phenylpyridine, 6-phenylpyridine, etc.), those of the 4- pyridine series (e. g.
  • Q represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing from 5 to 6 atoms in the heterocyclic ring, such as a thiazolone nucleus, for example, a 2,4(3,5)-thiazoledione nucleus, such as 2,4(3,5)-thiazoledione, 3-alkyl-2,4(3,5)-thiazolediones (e. g.
  • ethyl 3-phenyl or 3-a-naphthyl derivatives, a 2-alkylphenylamino-4(5)-thiazolone nucleus or a 2-diphenylamino-4(5)- thiazolone nucleus; an oxazolone nucleus, for example, a 2-thio-2,4(3,5)-oxazoledione nucleus, such as a 3-alkyl-2- thio-2,4(3,5)-oxazoledione nucleus (e. g.
  • l-ethyl or l,3-diall yl (e. g. 1,3-diethyl) derivatives; at 3,4-dihydro-2(1)-quinolone nucleus, such as 3,4-dihydro- 2(1)-quinolone (dihydrocarbostyril); a 3,4-dihydro-2(l)- quinoxalone nucleus, such as 3,4-dihydro-2(l)-quinoxalone (oxydihydroquinoxaline); 3-phenomorpholone (1,4,3- benzoxazine-3 (4)-one or benzo-fl-morpholone) nuclei; 1,4,2 benzothiazine-3(4)-one (ketodihydrobenzoparathiazine) nuclei, and the like six-membered heterocyclic nuclei.
  • 3,4-dihydro-2(1)-quinolone nucleus such as 3,4-dihydro- 2(1)-quinolone (d
  • an optical sensitizing dye is present during the formation of the silver halide and is more strongly adsorbed to the surface of the silver halide range than would be possible through simple mixing after preparation of the washed, finished emulsion.
  • the process of my invention does not extend to the use of other optical sensitizing dyes, such as those of the carbocyanine class.
  • the optical sensitizing dye can be incorporated in either the silver nitrate solution or the solution of watersoluble halide. I have found that it is especially advantageous to incoiporate the optical sensitizing dyes selected from those represented by Formula I above in the aqueous solution of silver nitrate containing a small amount of gelatin, since precipitation of the dye is substantially avoided.
  • Z R2 wherein R, Z and 12 each have the values given above, Q1 has the same values as those assigned above to Q, R1 represents an alkyl group of at least 7 carbon atoms, such as n-heptyl, n-octyl, n-nonyl, n-decyl, n-lauryl, etc., and R2 represents a hydrogen atom, an alkyl group, e. g. methyl, ethyl, etc., or an aryl group, e. g. phenyl, p-tolyl, etc., (e. g. a mononuclear aryl group of the benzene series).
  • R1 represents an alkyl group of at least 7 carbon atoms, such as n-heptyl, n-octyl, n-nonyl, n-decyl, n-lauryl, etc.
  • R2 represents a hydrogen atom, an
  • an emulsion which is capable of giving high contrast and is sensitive to blue can be mixed with an emulsion which is capable of giving low contrast and is sensitive to green (such as a spectrally sensitized silver bromide emulsion). If such a composite emulsion is exposed to light passing through a blue-green filter, the emulsion works normally and is suitable for negatives of normal gradation (contrast).
  • the light which acts upon the emulsion which is capable of giving high contrast is cut oil by means of a filter permeable only to green, and a normal picture is obtained by means of the emulsion which is capable of giving 10W contrast.
  • the light which acts upon the emulsion which is capable of giving low contrast is cut off by means of a filter permeable only to blue, and a normal picture is obtained by means of the emulsion which is capable of giving high contrast.
  • a variation of the above process involves the sensitization of the contrasty chloride emulsion instead of the bromide emulsion of lower contrast, to the green portion of the spectrum.
  • I incorporate the optical sensitizing dye in the silver halide emulsion of higher contrast, although it is possible to sensitize both emulsions according to my invention.
  • Typical sensitizing dyes selected from those represented by Formulas I and II above which can advantageously be used in my invention comprise the following, for example:
  • Example I The following solutions were prepared: Solution A:
  • a high contrast print was obtained by exposing through a Wratten No. 12 Filter (i. e. a filter which transmits substantially no light of wavelength shorter than about 495 mu, although there was about 1 per cent transmission of light of wavelength 300 to 340 mu).
  • a low contrast print was obtained by exposing through a Wratten No. 34 Filter (i. e. a filter having its maximum transmission between 315' and 500 mu, with no transmission between 500 mu and 635 mu).
  • Example 2 A mixture of silver chloride emulsions was obtained in exactly the same manner as described in 1 above except that 0.025 g. of 5-(3-methyl-2-thiazolinylidene)ethylidene 3 n heptyl 1 phenyl 2 thiohydantoin was used instead of the dye inSolution C of that example.
  • a high contrast print was obtained by exposing through a Wratten No. 12 Filter and a low contrast print was obtained by exposing through a Wratten No. 34 Filter.
  • one part of a high contrast photographic emulsion of silver chlorobromide (50% silver chloride and 50% silver bromide) sensitized with one of the dyes enumerated above can be mixed with two parts of a low contrast silver chlorobromiodide (6% silver chloride, silver bromide, and 4% silver iodide) emulsion to give a product showing varying degrees of contrast, even after artificial or simulated aging.
  • one part of a 50/50 chlorobromide emulsion of high contrast sensitized with one of the optical sensitizing dyes enumerated above can be mixed with two parts of a 20/80 chlorobromide emulsion of lower contrast to give a varying contrast emulsion, showing little or no change on simulated aging.
  • emulsion addenda such as antifoggants, coating aids, hardeners, and the like, can be incorporated in the silver halide emulsions prepared in accordance with my invention.
  • alkali metal halides used above in preparing silver halides according to my invention
  • other water-soluble halides such as the alkaline earth halides, ammonium halides, cadmium halides, etc. can be employed.
  • My invention is not to be construed as limited to any particular method of emulsion making, except as to the manner of precipitation of the silver halide as described above.
  • any of the methods of emulsion making described in the British patent can be used in practicing my invention.
  • the contrast of the emulsion of higher contrast is generally at least 2.5 times that of the emulsion of lower contrast. See, for example, Kridel U. S. Patent 2,358,169, issued September 12, 1944, and Davey and Knott U. S. Patent 2,318,597, issued May 11, 1943.
  • sensitizing dyes of the type represented by Formulas I and II above have been previously described in one or more of the following U. S. patents: 2,170,804, issued August 29, 1939; 2,l77,4012,177,403, issued October 24, 1939; 2,263,757, issued November 25, 1941; 2,265,908, issued December 9, 1941; and 2,282,116, issued May 5, 1952. See also Carroll U. S. application Serial No. 274,445, filed March 1, 1952 (now U. S. Patent 2,635,961, issued April 21, 1953), copending herewith, for a description of the preparation of such dye types.
  • the step which comprises combining the silver nitrate with the Water-soluble halide in the presence of an optical sensitizing dye selected from those represented by the following general formula:
  • R represents an alkyl group
  • L represents a methine group
  • d represents a positive integer of from 1 to 3
  • n represents a positive integer of from 1 to 2
  • Z and Q each represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing from. to 6 atoms in the heterocyclic ring, in the production of the emulsion of higher contrast and thereafter mixing the said emulsion of higher contrast containing the optical sensitizing dye and the said emulsion of lower contrast together.
  • a process of preparing a mixture of two silver halide emulsions at least one of the emulsions containing a sensitizing dye so that the emulsions have different spectral sensitivities, one of the emulsions having a contrast at least 2.5 times greater than that of the other emulsion, the steps which comprise admixing an aqueous alkali metal halide solution and an aqueous gelatin solution containing silver nitrate and an optical sensitizing dye selected from those represented by the following general formula:
  • R represents an alkyl group
  • L represents a mcthino group
  • d represents a positive integer of from 1 to 3
  • n represents a positive integer of from 1 to 2
  • Z and Q each represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing from 5 to 6 atoms in the heterocyclic ring, in the production of the emulsion of higher contrast, and thereafter mixing together the said optically sensitized emulsion of higher contrast with the said silver halide emulsion of lower contrast.
  • R represents an alkyl group of from 1 to 2 carbon atoms
  • R1 represents an alkyl group containing at least 7 carbon atoms
  • R2 represents a member selected from the group consisting of a hydrogen atom, an alkyl group of from 1 to 2 carbon atoms, and a mononuclear aromatic group of the benzene series
  • n represents a positive integer of from 1 to 2
  • Z and Q1 each represents the nonmetallic atoms necessary to complete a heterocyclic nucleus containing from 5 to 6 atoms in the heterocyclic ring, in the preparation of the emulsion of higher contrast, and thereafter mixing together the said sensitized emulsion of higher contrast with the said silver chloride emulsion of lower contrast.
  • R represents an alkyl group of from 1 to 2 carbon atoms
  • R represents a member selected from the group consisting of a hydrogen atom, an alkyl group of from 1 to 2 carbon atoms, and a mononuclear aromatic group of the benzene series
  • 11 represents a positive integer of from 1 to 2
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the thiazole series, benzothiazole series, a-naphthothiazole series, 3- naphthothiazole series, thiazoline series, oxazole series, benzoxazole series, ot-naphthoxazole series, fl-naphthoxazole series, selenazole series, benzoselenazole series, anaphthoselenazole series, fl-naphthoselenazole series, pyridine series, quinoline series
  • R represents an alkyl group of from 1 to 2 car bon atoms
  • R2 represents a member selected from the group consisting of a hydrogen atom, an alkyl group of from 1 to 2 carbon atoms, and a mononuclear aromatic group of the benzene series
  • n represents a positive integer of from 1 to 2
  • Z represents the non-metallic atoms necessary to complete a heterocyclie nucleus selected from the group consisting of those of the thiazole series, benzothiazole series, a-naphthothiazole series, B-naphthm thiazole series, thiazoline series, oxazole series, benzoxazole series, u-naphthoxazole series, fi-naphthoxazole series, selenazole series, benzosclenazole series, a-naphthoselenazole series, fi-naphthoselenazole series, pyridine
  • the steps which comprise admixing an aqueous alkali metal chloride solution and an aqueous gelatin solution containing silver nitrate and 5-[(3-methyl-2-thiazolinylidene)ethylidenel- B-n-heptyl-1-phenyl-2-thiohydantoin, in the preparation of the emulsion of higher contrast, and thereafter mixing together the said sensitized emulsion of higher contrast with the said silver chloride emulsion of lower contrast.
  • the steps which comprise admixing an aqueous gelatin solution containing silver nitrate and an aqueous alkali metal chloride solution containing 5 (3-ethyl-2 3 -benzoxazolylidene) isopropylidene]-3-n-heptylrhodanine in the preparation of the emulsion of higher contrast, and thereafter mixing together the said sensitized emulsion of higher contrast with the said silver chloride emulsion of lower contrast.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Plural Heterocyclic Compounds (AREA)
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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3152907A (en) * 1959-11-12 1964-10-13 Eastman Kodak Co Method for controlling speed and contrast of photographic emulsions
US3446619A (en) * 1964-11-16 1969-05-27 Eastman Kodak Co Radiation sensitive silver-dye complexes
FR2418479A1 (fr) * 1978-02-27 1979-09-21 Eastman Kodak Co Procede de preparation d'emulsions photosensibles aux halogenures d'argent, sensibilisees spectralement et emulsions ainsi preparees
US4183756A (en) * 1978-05-03 1980-01-15 Eastman Kodak Company Pre-precipitation spectral sensitizing dye addition process
US4225666A (en) * 1979-02-02 1980-09-30 Eastman Kodak Company Silver halide precipitation and methine dye spectral sensitization process and products thereof
EP0069596A3 (en) * 1981-07-07 1983-06-22 Konishiroku Photo Industry Co. Ltd. A method for production of a silver halide photographic light-sensitive material
US4476220A (en) * 1982-07-29 1984-10-09 Minnesota Mining And Manufacturing Company Spectrally sensitized photothermographic materials and preparation thereof
US4908303A (en) * 1987-02-12 1990-03-13 Fuji Photo Film Co., Ltd. Silver halide photographic materials spectrally sensitized with luminous dye
EP1251395A1 (en) 2001-04-17 2002-10-23 Fuji Photo Film Co., Ltd. Silver halide photographic material and methine dye
EP1914594A2 (en) 2004-01-30 2008-04-23 FUJIFILM Corporation Silver halide color photographic light-sensitive material and color image-forming method

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3469987A (en) * 1965-06-21 1969-09-30 Eastman Kodak Co Method of spectrally sensitizing photographic silver halide emulsions

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB326287A (en) * 1929-01-15 1930-03-13 Konrad Bialon Process for the manufacture of light-sensitive surfaces for use in colour photography
US1996928A (en) * 1930-03-19 1935-04-09 Leopold D Mannes Sensitized photographic element and process of making same
GB503845A (en) * 1936-10-14 1939-04-14 Kodak Ltd Sensitive elements for colour photography and methods for the production thereof
US2202026A (en) * 1937-03-18 1940-05-28 Ilford Ltd Photographic printing process and material
US2235426A (en) * 1937-10-14 1941-03-18 Goodman Mac Sensitized photographic element and process of making the same
US2284877A (en) * 1940-06-03 1942-06-02 Eastman Kodak Co Light sensitive color element
US2464780A (en) * 1945-12-07 1949-03-22 Gen Aniline & Film Corp Dye-sensitized photographic silver halide emulsion

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB326287A (en) * 1929-01-15 1930-03-13 Konrad Bialon Process for the manufacture of light-sensitive surfaces for use in colour photography
US1996928A (en) * 1930-03-19 1935-04-09 Leopold D Mannes Sensitized photographic element and process of making same
GB503845A (en) * 1936-10-14 1939-04-14 Kodak Ltd Sensitive elements for colour photography and methods for the production thereof
US2202026A (en) * 1937-03-18 1940-05-28 Ilford Ltd Photographic printing process and material
US2235426A (en) * 1937-10-14 1941-03-18 Goodman Mac Sensitized photographic element and process of making the same
US2284877A (en) * 1940-06-03 1942-06-02 Eastman Kodak Co Light sensitive color element
US2464780A (en) * 1945-12-07 1949-03-22 Gen Aniline & Film Corp Dye-sensitized photographic silver halide emulsion

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3152907A (en) * 1959-11-12 1964-10-13 Eastman Kodak Co Method for controlling speed and contrast of photographic emulsions
US3446619A (en) * 1964-11-16 1969-05-27 Eastman Kodak Co Radiation sensitive silver-dye complexes
FR2418479A1 (fr) * 1978-02-27 1979-09-21 Eastman Kodak Co Procede de preparation d'emulsions photosensibles aux halogenures d'argent, sensibilisees spectralement et emulsions ainsi preparees
US4183756A (en) * 1978-05-03 1980-01-15 Eastman Kodak Company Pre-precipitation spectral sensitizing dye addition process
US4225666A (en) * 1979-02-02 1980-09-30 Eastman Kodak Company Silver halide precipitation and methine dye spectral sensitization process and products thereof
EP0069596A3 (en) * 1981-07-07 1983-06-22 Konishiroku Photo Industry Co. Ltd. A method for production of a silver halide photographic light-sensitive material
US4476220A (en) * 1982-07-29 1984-10-09 Minnesota Mining And Manufacturing Company Spectrally sensitized photothermographic materials and preparation thereof
US4908303A (en) * 1987-02-12 1990-03-13 Fuji Photo Film Co., Ltd. Silver halide photographic materials spectrally sensitized with luminous dye
EP1251395A1 (en) 2001-04-17 2002-10-23 Fuji Photo Film Co., Ltd. Silver halide photographic material and methine dye
EP1914594A2 (en) 2004-01-30 2008-04-23 FUJIFILM Corporation Silver halide color photographic light-sensitive material and color image-forming method

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GB733731A (en) 1955-07-20
FR1097212A (fr) 1955-07-01

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