EP0465728A1 - Stabilisierung von tabularen Körnern durch Pyrimidinderivate - Google Patents

Stabilisierung von tabularen Körnern durch Pyrimidinderivate Download PDF

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Publication number
EP0465728A1
EP0465728A1 EP90201842A EP90201842A EP0465728A1 EP 0465728 A1 EP0465728 A1 EP 0465728A1 EP 90201842 A EP90201842 A EP 90201842A EP 90201842 A EP90201842 A EP 90201842A EP 0465728 A1 EP0465728 A1 EP 0465728A1
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EP
European Patent Office
Prior art keywords
photographic material
material according
emulsion
grains
tabular
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EP90201842A
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English (en)
French (fr)
Inventor
Marc Emiel Van Den Zegel
Piet Kok
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Agfa Gevaert NV
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Agfa Gevaert NV
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Priority to EP90201842A priority Critical patent/EP0465728A1/de
Priority to JP19490591A priority patent/JPH04234034A/ja
Publication of EP0465728A1 publication Critical patent/EP0465728A1/de
Withdrawn legal-status Critical Current

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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
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/16—X-ray, infrared, or ultraviolet ray processes
    • G03C5/17—X-ray, infrared, or ultraviolet ray processes using screens to intensify X-ray images
    • 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
    • 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
    • G03C1/0051—Tabular grain emulsions

Definitions

  • the present invention relates to photographic silver halide emulsion technology and more specifically to the stabilization of tabular silver halide emulsion grains.
  • Tabular grains are known in the photographic art for quite some time. As early as 1961 Berry et al described the preparation and growth of tabular silver bromoiodide grains in Photographic Science and Engineering, Vol 5, No 6. A discussion of tabular grains appeared in Duffin, Photographic Emulsion Chemistry, Focal Press, 1966, p. 66-72. Early patent literature includes Bogg US 4,063,951, Lewis US 4,067,739 and Maternaghan US 4,150,994, US 4,184,877 and US 4,184,878. However the tabular grains described herein cannot be regarded as showing a high diameter to thickness ratio, commonly termed aspect ratio. In a number of US applications filed Sep. 30, 1982 and issued in 1984 tabular grains with high aspect ratio and their advantages in photographic applications are described.
  • So Wilgus US 4,434,226 discloses tabular silver bromoiodide grains having a thickness less than 0.3 micron, a diameter of at least 0.6 micron and an average aspect ratio greater than 8:1 and accounting for at least 50 percent of the total projected area of all the emulsion grains.
  • Kofron US 4,439,520 discloses similar grains which are spectrally sensitized.
  • Abbott US 4,425,425 describes radiographic materials containing tabular grains with aspect ratio of at least 8:1 and Abbott US 4,425,426 discloses similar grains with an aspect ratio between 5:1 and 8:1.
  • Solberg US 4,433,048 protects tabular silver bromoiodide grains with inhomogeneously distributed iodide.
  • a survey on high aspect ratio silver halide emulsions appeared in Research Disclosure, Vol 225, Jan 1983, Item 22534.
  • High aspect ratio tabular grains exhibit several pronounced photographic advantages. Thanks to their particular morphology greater amounts of certain spectral sensitizers can be adsorbed per mole silver halide compared to classical globular grains. As a consequence such spectrally sensitized tabular grains show a wide separation between their blue speed and minus blue speed. Sharpness of photographic images can be improved using tabular grains thanks to their lower light scattering properties again compared to conventional globular emulsion grains. In color negative materials the conventional sequence of the light sensitive layers can be altered and the yellow filter layer can be omitted. In developed black-and-white images high covering power is obtained even at high hardening levels; alternatively reduced silver halide coverages can be achieved if wanted resulting again in improved sharpness.
  • the high light absorption of tabular grains in the spectrally sensitized region effectively reduces the "cross-over" which is the dominant factor for sharpness in a screen-film pair.
  • the "cross-over” is a measure of the photographic reponse of the respective emulsion layers to the exposure from the screen located at the opposite side of the double coated film. This emission has penetrated the second emulsion layer and the support, resulting in a reduced sharpness of the finally obtained radiographic image.
  • tabular grain emulsions need to be stabilized by antifoggants or stabilizers which minimize the fog increase during the processing of freshly coated photographic elements and/or the fog increase during extended storage periods of the said elements.
  • antifoggants or stabilizers which minimize the fog increase during the processing of freshly coated photographic elements and/or the fog increase during extended storage periods of the said elements.
  • Numerous classes of chemical compounds can be added as fog-inhibiting agent or stabilizer to conventional silver halide emulsions. Suitable examples are e.g.
  • heterocyclic nitrogen-containing compounds such as benzothiazolium salts, nitroimidazoles, nitrobenzimidazoles, chlorobenzimidazoles, bromobenzimidazoles, mercaptothiazoles, mercaptobenzothiazoles, mercaptobenzimidazoles, mercaptothiadiazoles, aminotriazoles, benzotriazoles (preferably 5-methyl-benzotriazole), nitrobenzotriazoles, mercaptopyrimidines, mercaptotriazines, benzothiazoline-2-thione and oxazoline-thione.
  • a especially useful class of compounds constitutute the azaindenes e.g.
  • triazaindenes triazaindenes, tetrazaindenes and pentazaindenes, especially those described by Birr in Z. Wiss. Phot. 47 (1952), pages 2-58 and the azaindenes disclosed by Heimbach in US 2,444,607, 2,444,609, 2,449,225 and 2,450,397.
  • the best commonly known and most widely used azaindene is 4-hydroxy-6-methyl-1,3,3a,7-tetraazaindene, furtheron abbreviated as TAI.
  • Other classes include triazolopyrimidines such as those described in GB 1,203,757, GB 1,209,146, JA-Appl. 75-39537, and GB 1,500,278 and other compounds such as benzenethiosulphonic acid, benzenethiosulphinic acid and benzenethiosulphonic acid amide compounds.
  • a widely used class of stabilizers is the class of mercaptotetrazoles, in particular 1-phenyl-5-mercaptotetrazole.
  • a set of specific substituted 1-phenyl-mercaptotetrazoles is disclosed as stabilizers for tabular grain emulsions in US 4,888,273.
  • TAI partially desorb spectral sensitizers from the grain surface, deteriorating in this way the speed in the corresponding spectral region, and in the case of double coated radiographic elements, increasing the cross-over due to a hypsochromic spectral shift of the desorbed green spectral sensitizer in the gelatin phase.
  • Lowering the tetraazaindene concentration renders the stabilization ineffective.
  • This problem with tetraazaindene stabilization gets more important in the case of low iodide content of the silver bromoiodide grains and is utmost severe with silver bromide emulsions containing no iodide at all.
  • tabular grains with minor or no iodide content are preferred because of their faster development and fixation rate compared to emulsions containing substantial amounts of iodide.
  • the desorption of spectral sensitizer is partially overcome by adding at the finalling stage of the emulsion preparation a certain amount of a soluble iodide salt but in this case the grain surface is partially converted to AgBrl which results in an inferior sensitivity.
  • Tabular grains having a minimal average aspect ratio of 4:1, and accounting for at least 50 % of the total projected area of all the emulsion grains are effectively stabilized with a mercapto-substituted pyrimidine derivative represented by the following general formula : wherein :
  • the stabilizer of use according to the invention is combined with another stabilizer of the tetraazaindene type e.g. 4-hydroxy-6-methyl-1,3,3a,7-tetraazaindene (TAI).
  • TAI 4-hydroxy-6-methyl-1,3,3a,7-tetraazaindene
  • the most effective stabilizing agent of these specific examples is Compound 1.
  • the stabilizers used according to the present invention can be added to a processing solution, e.g. a development bath, but preferably they are added to the photographic material itself. They can be added to any of the hydrophylic colloid layers of the photographic material, e.g. a non-light-sensitive intermediate layer, but preferably they are contained in the light-sensitive emulsion layer(s) where they are most easily adsorbed to the tabular silver halide grains in order to exercise properly their stabilizing function. They can be added in the form of an aqueous solution or a solution in an organic solvent, e.g. a methanolic solution, or in the form of a dispersion, e.g. a gelatineous dispersion possibly containing high-boiling oilformers. They are present in a concentration ranging preferably between 10- 7 and 10- 3 mole per mole silver halide.
  • a compound according to the present invention can be used as the sole stabilizing agent or it can be combined with any other representative substance of other known stabilizer classes.
  • a tetraazaindene stabilizer e.g. 4-hydroxy-6-methyl-1,3,3a,7-tetraazaindene (TAI).
  • TAI 4-hydroxy-6-methyl-1,3,3a,7-tetraazaindene
  • This tetrazaindene stabilizer is preferably present in a concentration ranging from 10- 6 to 10- 3 mole per mole silver halide.
  • the photographic tabular silver halide emulsions can be used in various types of photographic elements such as e.g. in photographic elements for graphic arts, for so-called amateur or professional still black-and- white and color photography, diffusion transfer reversal photographic elements, low-speed duplicating elements or high-speed camera sensitive elements and in motion picture recording.
  • the emulsions are incorporated in a highly sensitive radiographic element.
  • the photographic element can contain one single emulsion layer or it can be built up by two or even more emulsion layers.
  • the material contains blue, green and red sensitive layers each of which can be single or multiple.
  • the photographic material can contain several non-light sensitive layers, e.g. a protective layer, one or more backing layers, one or more subbing layers, and one or more intermediate layers.
  • a protective layer e.g. a protective layer, one or more backing layers, one or more subbing layers, and one or more intermediate layers.
  • an emulsion layer is provided on both sides of a transparent support covered on each side by a protective layer.
  • the halide composition of the tabular silver halide emulsions used according to the present invention is not specifically limited and may be any composition selected from e.g. silver chloride, silver bromide, silver iodide, silver chlorobromide, silver bromoiodide, and silver chlorobromoiodide.
  • a tabular silver bromoiodide emulsion is used, most preferably with a low iodide content up to 1 % or no iodide at all.
  • the tabular emulsion grains can be prepared by any method known in the art, e.g. by the methods disclosed in Research Disclosure, Vol 225, Jan 1983, Item 22534 cited above or by any similar or other method.
  • Their minimal average aspect ratio is 4:1.
  • Preferably their minimal average diameter is 0.6 micron and their maximal average thickness is 0.3 micron.
  • the emulsion can be desalted in the usual ways e.g. by dialysis, by flocculation and re-dispersing, or by ultrafiltration.
  • Two or more types of tabular silver halide emulsions that have been prepared differently can be mixed for forming a photographic emulsion for use in accordance with the present invention.
  • the size distribution of the tabular silver halide particles of the photographic emulsions to be used according to the present invention can be monodisperse or heterodisperse.
  • the tabular silver halide emulsions in connection with the present invention can be chemically sensitized as described e.g. in "Chimie et Physique Photographique” by P. Glafkides, in “Photographic Emulsion Chemistry” by G.F. Duffin, in “Making and Coating Photographic Emulsion” by V.L. Zelikman et al, and in "Die Grundlagen der Photographischen mit Silberhalogeniden” edited by H. Frieser and published by Akademische Verlagsgesellschaft (1968).
  • chemical sensitization can be carried out by effecting the ripening in the presence of small amounts of compounds containing sulphur e.g.
  • emulsions can be sensitized also by means of gold-sulphur ripeners or by means of reductors e.g. tin compounds as described in GB 789,823, amines, hydrazine derivatives, formamidine-sulphinic acids, and silane compounds.
  • reductors e.g. tin compounds as described in GB 789,823, amines, hydrazine derivatives, formamidine-sulphinic acids, and silane compounds.
  • the tabular silver halide emulsions can be spectrally sensitized with methine dyes such as those described by F.M. Hamer in "The Cyanine Dyes and Related Compounds", 1964, John Wiley & Sons.
  • Dyes that can be used for the purpose of spectral sensitization include cyanine dyes, merocyanine dyes, complex cyanine dyes, complex merocyanine dyes, hemicyanine dyes, styryl dyes and hemioxonol dyes.
  • Particularly valuable dyes are those belonging to the cyanine dyes, merocyanine dyes and complex merocyanine dyes.
  • a survey of useful chemical classes of spectral sensitizing dyes and specific useful examples in connection with tabular grains is given in the already cited Research Disclosure Item 22534.
  • spectral sensitization traditionally follows the completion of chemical sensitization. However, in connection with tabular grains, it is specifically considered that spectral sensitization can occur simultaneously with or even precede completely the chemical sensitization step.
  • green sensitization is preferred in connection with the actual tendency in medical X-ray practice to use screens containing green light emitting phosphors.
  • preferred green sensitizing compounds include anhydro-5,5'-dichloro-9-ethyl-3,3'-di-(3-sul- phobutyl)-oxacarbocyanine and the sulfopropyl containing analogous compound.
  • epitaxial deposition can occur at any stage of the emulsion preparation at the surface of the tabular grains, e.g by the addition of soluble silver salts or by the addition of very fine silver halide grains capable of Ostwald ripening. Epitaxial deposition at selected edge or corner sites is preferred. In this case the presence of a so-called site director, e.g. iodide ions can be beneficial.
  • site director e.g. iodide ions
  • the binder is a hydrophilic colloid, preferably gelatin.
  • Gelatin can, however, be replaced in part or integrallly by synthetic, semi-synthetic, or natural polymers.
  • Synthetic substitutes for gelatin are e.g. polyvinyl alcohol, poly-N-vinyl pyrrolidone, polyvinyl imidazole, polyvinyl pyrazole, polyacrylamide, polyacrylic acid, and derivatives thereof, in particular copolymers thereof.
  • Natural substitutes for gelatin are e.g. other proteins such as zein, albumin and casein, cellulose, saccharides, starch, and alginates.
  • the semi-synthetic substitutes for gelatin are modified natural products e.g. gelatin derivatives obtained by conversion of gelatin with alkylating or acylating agents or by grafting of polymerizable monomers on gelatin, and cellulose derivatives such as hydroxyalkyl cellulose, carboxymethyl cellulose, phthaloyl cellulose, and cellulose sulphates.
  • modified natural products e.g. gelatin derivatives obtained by conversion of gelatin with alkylating or acylating agents or by grafting of polymerizable monomers on gelatin
  • cellulose derivatives such as hydroxyalkyl cellulose, carboxymethyl cellulose, phthaloyl cellulose, and cellulose sulphates.
  • the gelatin can be lime-treated or acid-treated gelatin.
  • the preparation of such gelatin types has been described in e.g. "The Science and Technology of Gelatin", edited by A.G. Ward and A. Courts, Academic Press 1977, page 295 and next pages.
  • the gelatin can also be an enzyme-treated gelatin as described in Bull. Soc. Sci. Phot. Japan, N 16, page 30 (1966).
  • the binder of the photographic element can be hardened with appropriate hardening agents such as those of the epoxide type, those of the ethylenimine type, those of the vinylsulfone type e.g. 1,3-vinylsulphonyl-2-propanol, chromium salts e.g. chromium acetate and chromium alum, aldehydes e.g. formaldehyde, glyoxal, and glutaraldehyde, N-methylol compounds e.g. dimethylolurea and methyloldimethylhydantoin, dioxan derivatives e.g.
  • appropriate hardening agents such as those of the epoxide type, those of the ethylenimine type, those of the vinylsulfone type e.g. 1,3-vinylsulphonyl-2-propanol, chromium salts e.g. chromium acetate and chro
  • the photographic element of the present invention may further comprise various kinds of surface-active agents in the photographic emulsion layer or in at least one other hydrophilic colloid layer.
  • Suitable surface-active agents include non-ionic agents such as saponins, alkylene oxides e.g.
  • polyethylene glycol polyethylene glycol/polypropylene glycol condensation products, polyethylene glycol alkyl ethers or polyethylene glycol alkylaryl ethers, polyethylene glycol esters, polyethylene glycol sorbitan esters, polyalkylene glycol alkylamines or alkylamides, silicone-polyethylene oxide adducts, glycidol derivatives, fatty acid esters of polyhydric alcohols and alkyl esters of saccharides; anionic agents comprising an acid group such as a carboxy, sulpho, phospho, sulphuric or phosphoric ester group; ampholytic agents such as aminoacids, aminoalkyl sulphonic acids, aminoalkyl sulphates or phosphates, alkyl betaines, and amine-N-oxides; and cationic agents such as alkylamine salts, aliphatic, aromatic, or heterocyclic quaternary ammonium salts, aliphatic or heterocyclic ring
  • Such surface-active agents can be used for various purposes e.g. as coating aids, as compounds preventing electric charges, as compounds improving slidability, as compounds facilitating dispersive emulsification, as compounds preventing or reducing adhesion, and as compounds improving the photographic characteristics e.g higher contrast, sensitization, and development acceleration.
  • Preferred surface-active coating agents are compounds containing perfluorinated alkyl groups.
  • Development acceleration can be accomplished with the aid of various compounds, preferably polyalkylene derivatives having a molecular weight of at least 400 such as those described in e.g. US 3,038,805 - 4,038,075 - 4,292,400.
  • the photographic element of the present invention may further comprise various other additives such as e.g. compounds improving the dimensional stability of the photographic element, UV-absorbers, spacing agents and plasticizers.
  • Suitable additives for improving the dimensional stability of the photographic element are e.g. dispersions of a water-soluble or hardly soluble synthetic polymer e.g. polymers of alkyl(meth)acrylates, alkoxy-(meth)acrylates, glycidyl (meth)acrylates, (meth)acrylamides, vinyl esters, acrylonitriles, olefins, and styrenes, or copolymers of the above with acrylic acids, methacrylic acids, Alpha-Beta-unsaturated dicarboxylic acids, hydroxyalkyl (meth)acrylates, sulphoalkyl (meth)acrylates, and styrene sulphonic acids.
  • a water-soluble or hardly soluble synthetic polymer e.g. polymers of alkyl(meth)acrylates, alkoxy-(meth)acrylates, glycidyl (meth)acrylates, (meth)acrylamides, vinyl est
  • the average particle size of spacing agents is comprised between 0.2 and 10 um.
  • Spacing agents can be soluble or insoluble in alkali. Alkali-insoluble spacing agents usually remain permanently in the photographic element, whereas alkali-soluble spacing agents usually are removed therefrom in an alkaline processing bath.
  • Suitable spacing agents can be made e.g. of polymethyl methacrylate, of copolymers of acrylic acid and methyl methacrylate, and of hydroxypropylmethyl cellulose hexahydroph- thalate. Other suitable spacing agents have been described in US 4,614,708.
  • the support of the photographic material may be opaque or transparent, e.g. a paper support or resin support.
  • a paper support preference is given to one coated at one or both sides with an alpha-olefin polymer, e.g. a polyethylene layer which optionally contains an anti-halation dye or pigment.
  • an organic resin support e.g. cellulose nitrate film, cellulose acetate film, poly(vinyl acetal) film, polystyrene film, poly(ethylene terephthalate) film, polycarbonate film, polyvinylchloride film or poly-alpha-olefin films such as polyethylene or polypropylene film.
  • organic resin film is preferably comprised between 0.07 and 0.35 mm.
  • These organic resin supports are preferably coated with a subbing layer which can contain water insoluble particles such as silica or titanium dioxide.
  • the two emulsion layers are preferably coated on both sides of a transparent blue colored poly(ethylene terephthalate) film.
  • the photographic material containing tabular grains stabilized according to the present invention can be image-wise exposed by any convenient radiation source in accordance with its specific application.
  • suitable commercially available green light emitting screens are KODAK LANEX and AGFA CURIX ORTHO.
  • the photographic elements in connection with the present invention are preferably processed in an automatically operated apparatus.
  • commercially available X-ray material processors are CURIX U 242, marketed by AGFA-GEVAERT N.V. and KODAK RP-X-OMAT M6AN, marketed by EASTMAN KODAK Co.
  • tabular grains had an average thickness of 0.20 micron and an average aspect ratio of 6.6 as determined by the method described by Abott et al in GB 2,110,402. Of the total projected area 80 % was covered with tabular grains.
  • the emulsion was divided in aliquot portions. Each portion was spectrally sensitized to the green spectral region with 935 mg of anhydro-5,5'-dichloro-9-ethyl-3,3'-di-(3-sulphobutyl)-oxacarbocyanine and then chemically sensitized by means of 15.1 umole/mole AgNO 3 of sodium thiosulphate, 1.73 umole/mole AgN0 3 of chloroauric acid and 1.32 mmole/mole AgN0 3 of potassium thiocyanate. The time of chemical senstization was adjusted for each sample in order to obtain an optimal fog/density ratio after coating and processing.
  • each emulsion sample was coated on both sides of a polyethyleneterephtalate film at a silver coverage of 2 x 3.0 g expressed as AgN0 3 /m 2 .
  • a protective layer containing 1.1 g gelatin/m 2 was applied on both sides and as a hardener formaldehyde was used.
  • the coated samples were exposed to green light having a peak emission at 545 nm through a continuous tone wedge. Part of the samples were stored at 57 ° C and 34 % relative humidity in order to simulate an extended shelf life period. Processing was performed in a X-ray film processor (90 s cycle) using following processing solutions : a developing solution adjusted to pH 10.1 comprising hydrochinon, 1-phenyl-5-pyrazolidinone, potassium sulphite, 5-nitroindazole and glutaric dialdehyde as mean ingredients and a conventional fixing solution comprising ammonium thiosulphate adjusted to pH 4.3.
  • Table 1 illustrates the sensitometric results of the stabilization of the described tabular grains by 4-hydroxy-6-methyl-1,3,3a,7-tetraazaindene (TAI) and 2-mercapto-4-hydroxy-6-carboxy-quinazoline (compound 1), a stabilizer of the present invention. Sensitivities are expressed as relative arithmetic values, sample 1 having reference value 100. Table 2 presents the corpual cross-over values.
  • TAI 4-hydroxy-6-methyl-1,3,3a,7-tetraazaindene
  • compound 1 2-mercapto-4-hydroxy-6-carboxy-quinazoline

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
EP90201842A 1990-07-09 1990-07-09 Stabilisierung von tabularen Körnern durch Pyrimidinderivate Withdrawn EP0465728A1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP90201842A EP0465728A1 (de) 1990-07-09 1990-07-09 Stabilisierung von tabularen Körnern durch Pyrimidinderivate
JP19490591A JPH04234034A (ja) 1990-07-09 1991-07-08 ピリミジン誘導体による板状粒子の安定化

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EP90201842A EP0465728A1 (de) 1990-07-09 1990-07-09 Stabilisierung von tabularen Körnern durch Pyrimidinderivate

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5576432A (en) * 1994-12-23 1996-11-19 Eastman Kodak Company Process for the manufacture of dihydropyrimidines

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20000015014A (ko) * 1998-08-26 2000-03-15 김영환 신규의 포토레지스트용 단량체, 중합체 및 이를 이용한 포토레지스트 조성물

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2073677A5 (de) * 1969-12-13 1971-10-01 Agfa Gevaert Ag
US4425426A (en) * 1982-09-30 1984-01-10 Eastman Kodak Company Radiographic elements exhibiting reduced crossover
EP0244718A2 (de) * 1986-05-08 1987-11-11 Minnesota Mining And Manufacturing Company Lichtempfindliche Silberhalogenidemulsion und radiographische Elemente mit einer verbesserten Bildqualität und zurückbleibenden reduzierten Flecken

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2073677A5 (de) * 1969-12-13 1971-10-01 Agfa Gevaert Ag
US4425426A (en) * 1982-09-30 1984-01-10 Eastman Kodak Company Radiographic elements exhibiting reduced crossover
US4425426B1 (de) * 1982-09-30 1988-08-09
EP0244718A2 (de) * 1986-05-08 1987-11-11 Minnesota Mining And Manufacturing Company Lichtempfindliche Silberhalogenidemulsion und radiographische Elemente mit einer verbesserten Bildqualität und zurückbleibenden reduzierten Flecken

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JOURNAL OF IMAGING SCIENCE vol. 32, no. 4, July/August 1988, pages 160-177, Springfield, VA, US; J.E. MASKASKY: "Epitaxial Selective Site Sensitization of Tabular Grain Emulsions" *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5576432A (en) * 1994-12-23 1996-11-19 Eastman Kodak Company Process for the manufacture of dihydropyrimidines

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