US3869290A - Photographic silver halide elements of the Lippmann-type - Google Patents

Photographic silver halide elements of the Lippmann-type Download PDF

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Publication number
US3869290A
US3869290A US303403A US30340372A US3869290A US 3869290 A US3869290 A US 3869290A US 303403 A US303403 A US 303403A US 30340372 A US30340372 A US 30340372A US 3869290 A US3869290 A US 3869290A
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United States
Prior art keywords
emulsion
silver halide
photographic
lippmann
compounds
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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US303403A
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English (en)
Inventor
Herman Adelbert Philippaerts
Robert Joseph Pollet
Antoon Leon Vandenberghe
Jozef Frans Willems
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Agfa Gevaert NV
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Agfa Gevaert NV
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/70—Sulfur atoms
    • C07D277/74—Sulfur atoms substituted by carbon atoms
    • 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
    • G03C1/09—Noble metals or mercury; Salts or compounds thereof; Sulfur, selenium or tellurium, or compounds thereof, e.g. for chemical sensitising
    • 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
    • G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
    • G03C1/346—Organic derivatives of bivalent sulfur, selenium or tellurium
    • 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
    • G03C2001/03511—Bromide content
    • 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
    • G03C2200/34—Hydroquinone
    • 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
    • G03C2200/38—Lippmann (fine grain) emulsion
    • 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
    • G03C2200/45—Polyhydroxybenzene

Definitions

  • R is hydrogen, acyl, haloacyl or acyl carrying a quaternary ammonium group
  • R is an aliphatic, aromatic or heterocyclic group
  • R is hydrogen, the group ,SR or one or more substituents selected from alkyl, aryl, halogen, hydroxyl or alkoxy;
  • the compounds reduce distortions of image-details, enhance image-sharpness and reduce yellowing upon reversal processing.
  • the photographic materials for use in the production of masks as described above should have a high resolving power and acutance, and allow a correct reproduction of the dimensions of the image. However, with 30 fluence of closely adjacent image details and the image sharpness does not always meet the requirements.
  • R stands for an aliphatic group, more particularly alkyl including substituted alkyl e.g. alkyl substituted with carboxy, with aryl or with a heterocycle, an'aromatic group more particularly aryl including substituted aryl e.g. aryl substituted with halogen or 'with C,C alkyl, or preferably a heterocyclic group, e.g. a l-substituted S-tetrazolyl group and a Z-benzothiazolyl group, and
  • R represents hydrogen, the group -SR, or one or more of the known substituents used in hydroqui none-type developing'agents e.g. alkyl, aryl, halogen, hydroxyl, alkoxy, etc.
  • the precipitate was purified by dissolution in 800 ml of boiling ethylene glycol monomethyl ether and precipitation by means of 1600 ml of water. Yield 98 g (71 7a). Melting point 205C.
  • the compounds for use in accordance with the present invention are incorporated in the emulsion layer by addition, as a solution or dispersion, to the coating compositions of the Lippmann emulsion.
  • the concentration of the compounds used according to the invention depends on the characteristics of both the chosen compound and the emulsion and is therefore best determined by trial. In most cases the optimum concentration in the silver halide emulsion is between about 20 mg and about 2 g, preferably between about 100 mg and 1 g per mole of silver halide.
  • the thickness of the emulsion layer of a photographic material according to the present invention is generally comprised between about 3 microns and about 8 microns, and the average grain size of the silver halide grains is generally less than 80 nm.
  • the ratio of silver halide to hydrophilic colloid binder in the Lipp' mann emulsion according to the present invention is preferably at least 1:2 and at most 4:1.
  • the silver halide Lippmann emulsions may be prepared according to methods well known in the art and described in the literature (see e.g. P. Glafkids Photographic Chemistry", .Vol. 1, 1958, pages 365-368, Mees/James The theory of the Photographic Process", 1966, p. 36 and National Physical Laboratory Notes on Applied Science no. 20 Small Scale preparation of fine-grain (colloidal) Photographic emulsions, B. H. Crawford, London, 1960). They may also be prepared according to the technique described in co-pending United Kingdom Pat. Application No. 15,948/70.
  • Silver halide Lippmann-emulsions with very fine grain can be obtained by effecting the precipitation of the silver halide in the presence of heterocyclic mercapto compounds as described in United Kingdom Pat. Specification No. 1,204,623 or in the presence of compounds as described in co-pending United Kingdom Pats. Nos. 1,320,138 and 1,318,518.
  • the hydrophilic colloid used as the vehicle for the silver halide may be any of the common hydrophilic colloids employed in photographic light-sensitive emulsions for example, gelatin, albumin, zein, casein, alginic acid, a cellulose derivative such as carboxymethyl cellulose, a synthetic hydrophilic colloid such as polyvinyl alcohol and poly-N-vinyl pyrrolidone, etc. If desired compatible mixtures of two or more colloids may be employed for dispersing the silver halide.
  • silver salts may be used as the light-sensitive salt such as silver bromide, silver iodide, silver chloride, or mixed silver halides such as silver chlorobromide, silver bromoiodide and silver chlorobromoiodide.
  • Silver bromide emulsions which may have a iodide content of at most 8 mole /1 and having an average grainsize of at most 80 nm are favoured.
  • the emulsions may be coated on a wide variety of photographic emulsion supports.
  • Typical supports include cellulose ester film, polyvinyl acetal film, polystyrene film, polyethylene terephthalate film and related films of resinous material as well as paper and glass.
  • glass supports are most advantageously used in view of their high dimensional stability.
  • the light-sensitive silver halide emulsions of use in the preparation of a photographic material according to the present invention may be chemically as well as spectrally sensitized.
  • the silver halide emulsions for microelectronic mask making according to the present invention are most advantageously sensitized for the green 5 region of the spectrum.
  • the exposure light is preferably chosen so that it radiates light of a. wavelength to which the emulsion has been spectrally sensitized.
  • sulphur containing compounds such as allyl thiocyanate. allyl thiourea, sodium thiosulphate, etc.
  • the emulsions may also be sensitized by means of reductors for instance tin compounds as described in French Pat. Specification No. 1,146,955 and in Belgian Pat. Specification No. 568,687, imino-amino methane sulphinic acid compounds as described in United Kingdom Pat. Specification No. 789,823 and small amounts of noble metal compounds such as gold, platinum, palladium, iridium, ruthenium and rhodium.
  • the said emulsions may also comprise compounds which sensitize the emulsion by development acceleration for example compounds of the polyoxyalkylene type such as alkylene oxide condensation products as described among other in US. Pats. Nos. 2,531,832
  • the emulsions may comprise stabilizers e.g. heterocyclic nitrogen-containing thioxo compounds such as benzothiazoline-Z-thione and l-phenyl-2-tetrazoline-S-thiohe and compounds of the hydroxytriazolopyrimidine type. They can also be stabilized with mercury compounds such as the mercury compounds described in Belgian Pat. Specifications Nos. 524,121 and 677,337, United Kingdom Pat. Specification No. 1,173,609 and in US. Pat. No. 3,179,520.
  • stabilizers e.g. heterocyclic nitrogen-containing thioxo compounds such as benzothiazoline-Z-thione and l-phenyl-2-tetrazoline-S-thiohe and compounds of the hydroxytriazolopyrimidine type. They can also be stabilized with mercury compounds such as the mercury compounds described in Belgian Pat. Specifications Nos. 524,121 and 677,337, United Kingdom Pat. Specification No. 1,173,609 and
  • the emulsions may also comprise light-absorbing dyes which are so chosen that they absorb light of the wavelength to which the material is exposed so that scattering and reflection of light within the photographic material is reduced.
  • light-absorbing dyes which are so chosen that they absorb light of the wavelength to which the material is exposed so that scattering and reflection of light within the photographic material is reduced.
  • the dyes are preferably used in such amounts that per micron of emulsion layer thickness a density comprised between 0.05 and 0.20, measured in the spectral region of the exposure light, is obtained.
  • any of the hardening agents for hydrophilic colloids may be used in the emulsions according to the present invention such as chromium, aluminium, and zirconium salts, formaldehyde, dialdehydes, hydroxy aldehydes, acrolein, glyoxal, halogen substituted aldehyde acids such as mucochloric acid and mucobromic acid, diketones such as divinyl ketone, compounds carrying one or more vinylsulphonyl groups such as divinylsulphone, l,3,5-trivinylsulphonylbenzene, hexahydro-striazines carrying vin ylcarbonyl, halogenoacetyl and/or acyl groups such as l,3,5-triacryloylhexahydro l,3,5- triazine, 1,3-diacryloyl-5-acetylhexahydro-l ,3 ,5- triazin
  • the silicon compounds described in co-pending United Kingdom Pat. No. l,286,467 can be incorporated into the emulsion.
  • the light-sensitive emulsions may also comprise all other kinds of ingredients such as plasticizers, coating aids, etc.
  • Example 1 A silver bromide emulsion comprising per kg 72 g of silver bromide and 93 g of gelatin was prepared by simultaneous addition of a silver nitrate solution and a potassium bromide solution to a 3 7c aqueous solution of gelatin. The conditions of precipitation were adjusted so that a Lippmann emulsion with an average grain size of 70 nm was obtained. Details as to the preparation of Lippmann emulsions can be found amongst others in P. Glafkids Photographic Chemistry", Vol. I, 1958, Fountain Press, London.
  • the emulsion was divided into 4 portions and to each portion, except for one, one ofthe compounds 1,4 and 5 respectively was added in an amount of 500 mg per mole of silver halide.
  • the emulsion portions were coated on glass plates pro rata of 230 ml per sq.m so as to obtain after drying a layer thickness of 6 ,u.
  • the 4 plate materials A, B. C and D were then exposed under identical circumstances by means of monochromatic light, the spectral composition of which corresponds with the absorption region of the light-absorbing dye used, through a test pattern, as normally used for the quantitative evaluation of materials for use in microelectronics maskmaking, consisting of lines which are separated by spaces of the same width as the lines themselves and with a width varying from 1 to 20 ,u..
  • the exposure was of such an intensity so as to limit the density in the transparent areas of the images produced, which correspond with the white lines of the test pattern, to the fog value.
  • the exposed materials were first developed for about 5 min. in the following developing liquid the pH of which was adjusted to l05 hydroquinone monomethyl-p-aminophenyl hemisulphate potassium bromide sodium carbonate sodium sulphite potassium thiocyanate water to make The materials were then treated for about 5 min. in
  • Example 1 was repeated with the difference that materials A to D were processed so as to obtain a negative image by means of a developing liquid of the following composition water 800 ml monomethyl-p-aminophcnol hemisulphate l.5 g sodium sulphIte (anhydrous) 25 g hydroquinone 6 g sodium carbonate (anhydrous) 40 g potassium bromide l g water to make 1 itre.
  • materials B, C and D showed improved image-sharpness and less distortions in line-reproduction.
  • Photographic silver halide emulsion including a silver halide and hydrophilic colloid binder, said emulsion being of the Lippmann type having an average grain size of less than 100 nm and comprising from 20 mg to 2 g per mole of silver halide of a compound of the formula:
  • stituents selected from alkyl, aryl, halogen, hydroxyl and alkoxy; the ratio of silver halide to hydrophilic colloid binder in the emulsion being from 1 2 and 4 l.
  • Photographic emulsion according to claim 1 wherein in the formula R, stands for l'substituted 5- tetrazolyl or for Z-benzothiazolyl and both R nd R are hydrogen.
  • Photographic material comprising a support and an emulsion as defined in claim 1.
  • Photographic material according to claim 4 wherein the support is a glass sup-port.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (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)
  • Thiazole And Isothizaole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US303403A 1971-11-10 1972-11-03 Photographic silver halide elements of the Lippmann-type Expired - Lifetime US3869290A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5228971A GB1402420A (en) 1971-11-10 1971-11-10 Silver halide emulsions of the lippmann-type

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US3869290A true US3869290A (en) 1975-03-04

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Country Status (8)

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US (1) US3869290A (enExample)
JP (1) JPS5611938B2 (enExample)
BE (1) BE790873A (enExample)
CA (1) CA1006035A (enExample)
DE (1) DE2254357C3 (enExample)
FR (1) FR2159288B1 (enExample)
GB (1) GB1402420A (enExample)
SU (1) SU463274A3 (enExample)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4569903A (en) * 1980-02-11 1986-02-11 Fuji Photo Film Co., Ltd. Optical recording medium
US4814263A (en) * 1987-07-21 1989-03-21 Minnesota Mining And Manufacturing Company Direct-positive silver halide emulsion
JP2015160914A (ja) * 2014-02-27 2015-09-07 Jsr株式会社 重合体、化合物、樹脂組成物、樹脂ペレット及び樹脂成形体

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5821629B2 (ja) * 1973-12-19 1983-05-02 富士写真フイルム株式会社 ハイドロキノンカゴウブツ ノ セイゾウホウホウ
GB1569109A (en) * 1975-12-12 1980-06-11 Agfa Gevaert Lippmann-emulsions and reversal processing thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3379529A (en) * 1963-02-28 1968-04-23 Eastman Kodak Co Photographic inhibitor-releasing developers
US3705038A (en) * 1970-01-20 1972-12-05 Agfa Gevaert Nv Spectral sensitization of silver halide lippmann emulsions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1553483A (enExample) * 1967-02-23 1969-01-10

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3379529A (en) * 1963-02-28 1968-04-23 Eastman Kodak Co Photographic inhibitor-releasing developers
US3705038A (en) * 1970-01-20 1972-12-05 Agfa Gevaert Nv Spectral sensitization of silver halide lippmann emulsions

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4569903A (en) * 1980-02-11 1986-02-11 Fuji Photo Film Co., Ltd. Optical recording medium
US4814263A (en) * 1987-07-21 1989-03-21 Minnesota Mining And Manufacturing Company Direct-positive silver halide emulsion
JP2015160914A (ja) * 2014-02-27 2015-09-07 Jsr株式会社 重合体、化合物、樹脂組成物、樹脂ペレット及び樹脂成形体

Also Published As

Publication number Publication date
FR2159288B1 (enExample) 1976-06-04
JPS4859826A (enExample) 1973-08-22
DE2254357A1 (de) 1973-05-17
DE2254357B2 (de) 1981-06-11
FR2159288A1 (enExample) 1973-06-22
DE2254357C3 (de) 1982-02-11
CA1006035A (en) 1977-03-01
BE790873A (nl) 1973-05-03
SU463274A3 (ru) 1975-03-05
GB1402420A (en) 1975-08-06
JPS5611938B2 (enExample) 1981-03-18

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