US2586168A - Process of hardening gelatin and photographic gelatin emulsions - Google Patents
Process of hardening gelatin and photographic gelatin emulsions Download PDFInfo
- Publication number
- US2586168A US2586168A US760488A US76048847A US2586168A US 2586168 A US2586168 A US 2586168A US 760488 A US760488 A US 760488A US 76048847 A US76048847 A US 76048847A US 2586168 A US2586168 A US 2586168A
- Authority
- US
- United States
- Prior art keywords
- gelatin
- hardening
- dimethylol
- diketopiperazine
- photographic
- 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
Links
- 108010010803 Gelatin Proteins 0.000 title claims description 48
- 229920000159 gelatin Polymers 0.000 title claims description 48
- 239000008273 gelatin Substances 0.000 title claims description 48
- 235000019322 gelatine Nutrition 0.000 title claims description 48
- 235000011852 gelatine desserts Nutrition 0.000 title claims description 48
- 238000000034 method Methods 0.000 title claims description 15
- 239000000839 emulsion Substances 0.000 title description 43
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 claims description 48
- ANCDPTCUGLSMJJ-UHFFFAOYSA-N 1,4-bis(hydroxymethyl)piperazine-2,3-dione Chemical compound OCN1CCN(CO)C(=O)C1=O ANCDPTCUGLSMJJ-UHFFFAOYSA-N 0.000 claims description 30
- 238000000576 coating method Methods 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 11
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 42
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- -1 formaldehyde, hydroxy aldehydes Chemical class 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 8
- 230000032683 aging Effects 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- YJJCHWPBSSONRM-UHFFFAOYSA-N 1,4-bis(hydroxymethyl)piperazine-2,5-dione Chemical compound OCN1CC(=O)N(CO)CC1=O YJJCHWPBSSONRM-UHFFFAOYSA-N 0.000 description 3
- 230000002939 deleterious effect Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 150000005204 hydroxybenzenes Chemical class 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- IXWOUPGDGMCKGT-UHFFFAOYSA-N 2,3-dihydroxybenzaldehyde Chemical class OC1=CC=CC(C=O)=C1O IXWOUPGDGMCKGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- 238000000586 desensitisation Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- 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
- G03C1/30—Hardeners
Definitions
- This invention relates to the hardening of gelatin, and especiallyto the hardening of photographic gelatin and gelatino silver-halide emulsions to yield compositions having an appreciable increase in melting point and good stability on ageing with respect to fog, speed, and gradation.
- Compounds which have been used for hardening gelatin as such or in silver-halide emulsions are formaldehyde, hydroxy aldehydes, acrolein, glyoxal, and derivatives thereof, and mixtures of an aliphatic aldehyde with an aromatic compound containing at least one nuclear hydroxy substituent group such as phenol, resorcinol, resorcyclic aldehyde, and the like.
- formaldehyde and hydroxy aldehydes are satisfactory as hardening agents, these compounds possess the undesirable property of producing excessive fog, desensitization, or flattening of gradation in the processed film.
- Another object is to provide gelatin layers and gelatino silver-halide emulsion layers in which the gelatin is not subject to the phenomenon known as after-hardening.
- a further object is to provide a gelatino silverhalide emulsion which will not fog on storage.
- a still further object is to provide a gelatino silver-halide emulsion which will be resistant to relatively high processing temperatures without fogging, loss of speed, and loss of gradation.
- R represents either hydrogen or an alkyl group of not more than 4 carbon atoms, e. g.,
- the compounds which alone possess little or no hardening effect on gelatin or gelatino silverhalide emulsions, and which may be added in conjunction with the dimethylol-diketopiperazine, are 2,4-dihydroxy benzaldehyde (resorcylic aldehyde) and 1,3-benzenediol (resorcinol).
- the function of 2,4-dihydroxy benzaldehyde in the mixture is to boost or accelerate the hardening action of the dimethylol-diketopiperazine.
- resorcinol is added to this combination, the optimum in hardening as well as in photographic properties is obtained.
- a very desirable increase in melting point of gelatin or gelatino silver-halide emulsions is obtained by the utilization of dimethylol-diketopiperazines alone, said increase in melting point being unaccompanied by any tendency for the gelatin or emulsion to undergo the phenomenon of after-hardening. 7
- the invention contemplates the utilization of the dimethylol-diketopiperazines alone to eflect hardening while avoiding the phenomenon of after-hardening, it likewise contemplates the employment with the dimethylol-diketopiperazines of 2,4-dihydroxy benzaldehyde and resorcinol either alone or together. Inasmuch as best results are obtained when all three components are employed, the use of the same represents the preferred embodiment of the invention.
- 2,4-dihydroxy benzaldehyde is the only one to accelerate the hardening effect of the dimethylol-diketopiperazines without impairing the photographic characteristics of the emulsions
- resorcinol was found to be the only one, when in an admixture with a dimethylol-diketopiperazine and 2,4-dihydroxy benzaldehyde, to act as a stabilizing agent so as to impart excellent additional stability to the emulsion with respect to fog, speed, and gradation.
- a sufficient quantity of the dimethyloldiketopiperazine alone is added. While the exact amount of the dimethylol-diketopiperazine may be varied within wide limits and with due regard to the particular type of gelatin dispersion employed, in general, amounts ranging from 0.05% to 2.5% based on the dry weight of gelatin in the dispersion are preferred. In these amounts, effective hardening is obtained without after-hardening, i. e., the melting point of the gelatin does not vary with time or with long periods of storage prior to actual use and. processing of the photographic material provided with such a layer.
- a mixture of the dimethylol-diketopiperazine and 2,4-dihydroxy benzaldehyde is employed.
- the amount of 2,4-dihydroxy benzaldehyde to be added may vary from 0.005% to 2.5% based on the dry Weight of gelatin.
- v amounts of the dimethylol-diketopiperazine may 0 vary from 1 to 5 parts by weight, the amount of 2,4-dihydroxy benzaldehyde may vary from 0.1 to 5 parts by weight, and the amount of resorcinol may vary from 1 to 10 parts by weight per 10 kilogram of emulsion containing 840% gelatin.
- gradation of a silyenhalide emulsion I prefer to use resorcinol inconjunction with the. .dimethylolr' diketopiperazine and. 2,4-dihydroxy benzaldehyde. It is to be understood, however, that these emulsions may also be hardened by mixing therewith prior to coating the dimethylolediketopiperazine alone or in combination with 2,4-dihydroxy benzaldehyde. In the latter case the melting point of the gelatin rises appreciably without the attendant serious loss of photographic characteristics.
- Example II EXAMPLE II Example I was repeated with the exception that 40 mls. of 1,4-dimethylol-3,6-dimethyl-2,5- diketopiperazine was substituted for 40 mls. of lA-dimethylol-2,5-diketopiperazine. The results obtained were practically identical with those of Example I.
- Example III Example I was again repeated with the exception that 40 mls. of 1,4-dimethylol-3,6diisopropyl-2,5-diketopiperazine was substituted for 40 mls. of 1,4-dimethylol-2,5-diketopiperazine.
- EXAMPLE IV To a liter of a photographic silver-halide emulsion, containing 8-10% aqueous gelatin and melting at C., mls. of a 0.25% aqueous solution of 1,4-dimethylol-2,5-diketopiperazine and 40 mls. each of a 1.25% aqueous solution of 2,4-dihydroxy benzaldehyde and resorcinol were added at a temperature of40 C. A glass plate was coated with a thin layer of this emulsion and dried at room temperature. The emulsion layer melted at 49 C., and the film was tougher than the film of Example I. After ageing for 18 days, the melting point was substantially unchanged. Similar stability on ageing was obtained with respect to photographic characteristics.
- EXAMPLE'VI This example shows the effect on fog in a silver-halide emulsion containing 8-10% of gelatin by a mixture of 1,4-dimethylol-3,6-di-isopropyl-2,5diketopiperazine, 2,4-dihydroxy benzaldehyde, and resorcinol. All parts are in per cent based on the dry weight of the gelatin in the emulsion.
- my invention is not only applicable to the preparation of photographic silver-halide emulsions of satisfactory hardening properties, but also to the preparation of gelatin dispersions and dispersions of gelatin substitutes, which are normally capable of being hardened with formaldehyde, especially those which are and have been used in the preparation of various coatings or layers on paper, cloth, film, glass, and other surfaces.
- R represents a member selected from the class consisting of hydrogen, and an alkyl group of not more than 4 carbon atoms and a phenyl group.
- R represents a member selected from the classconsisting of hydrogen, and an alkyl group of not more than 4 carbon atoms and a phenyl group.
- the method of producing a hardened gelatin layer in a photographic silver-halide element having no after-hardening tendency which comprises uniformly mixing therewith, prior to coating upon a support, 2,4-dihydroxy benzaldehyde,
- a photo-sensitive element comprising a support and a gelatin silver-halide emulsion coated thereon, said emulsion containing as hardening means a dimethylol-diketopiperazine characterized by the following general formula:
- R represents a member selected from the class consisting of hydrogen, and an alkyl group of not more than 4 carbon atoms and a phenyl group.
- a photo-sensitive element comprising a support and a gelatin silver-halide emulsion coated thereon, said emulsion containing as hardening means 2,4-dihydroxy benzaldehyde and a dimethylol-diketopiperazine characterized by the following general formula:
- R tH Nom011 oH-o R 1% wherein R represents a member selected from the class consisting of hydrogen, and an alkyl group of not more than 4 carbon atoms and a phenyl group.
- a photo-sensitive element comprising a support and a gelatin silver-halide emulsion coated thereon, said emulsion containing as hardening means a mixture of 2,4-dihydroxy benzaldehyde, resorcinol, and a dimethylol-diketopiperazine of the following formula:
- a photo-sensitive element comprising a support and a gelatin silver-halide emulsion coated thereon, said emulsion containing as hardening means a mixture of 2,4-dihydroxy benzalde- 10 hyde, resorcinol, and a dimethylol-diketopiperazine of the following formula:
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE483860D BE483860A (en)) | 1947-07-11 | ||
| US760488A US2586168A (en) | 1947-07-11 | 1947-07-11 | Process of hardening gelatin and photographic gelatin emulsions |
| GB8363/48A GB639097A (en) | 1947-07-11 | 1948-03-20 | A process of hardening gelatin and photgraphic gelatin emulsions |
| FR968167D FR968167A (fr) | 1947-07-11 | 1948-06-23 | Procédé de production de gélatine photographique durcie et matériels photo-sensibles contenant de la gélatine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US760488A US2586168A (en) | 1947-07-11 | 1947-07-11 | Process of hardening gelatin and photographic gelatin emulsions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2586168A true US2586168A (en) | 1952-02-19 |
Family
ID=25059248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US760488A Expired - Lifetime US2586168A (en) | 1947-07-11 | 1947-07-11 | Process of hardening gelatin and photographic gelatin emulsions |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2586168A (en)) |
| BE (1) | BE483860A (en)) |
| FR (1) | FR968167A (en)) |
| GB (1) | GB639097A (en)) |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2950197A (en) * | 1955-04-18 | 1960-08-23 | Eastman Kodak Co | Hardening of gelatin |
| US2969392A (en) * | 1957-12-30 | 1961-01-24 | Union Oil Co | Amidomethylation of aromatic hydrocarbons |
| US3119825A (en) * | 1961-03-08 | 1964-01-28 | Staley Mfg Co A E | Methylol leucine diketopiperazines |
| US3128180A (en) * | 1958-07-02 | 1964-04-07 | Eastman Kodak Co | Hardened high-contrast photographic silver chloride emulsions and method of processing |
| US3288775A (en) * | 1961-04-07 | 1966-11-29 | Ciba Ltd | Method of hardening gelatin by reacting with conjugated heterocyclic compounds containing halogen atoms and water-solubilizing acid groups |
| US3372030A (en) * | 1962-12-14 | 1968-03-05 | Pavelle Corp | Method of shortening the processing time of color photography |
| US3380828A (en) * | 1965-08-02 | 1968-04-30 | Eastman Kodak Co | Antistain agents for spectrally sensitized silver halide photographic elements |
| US3649281A (en) * | 1967-10-04 | 1972-03-14 | Fuji Photo Film Co Ltd | Photographic processing for photographic silver halide light-sensitive elements |
| US3775128A (en) * | 1971-08-25 | 1973-11-27 | Fuji Photo Film Co Ltd | Silver halide emulsion containing a triazine as antifoggant |
| JPS491223A (en)) * | 1972-04-17 | 1974-01-08 | ||
| US4009036A (en) * | 1973-12-13 | 1977-02-22 | Agfa-Gevaert A.G. | Photographic developer |
| EP0124795A2 (en) | 1983-04-11 | 1984-11-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion |
| WO2008038764A1 (fr) | 2006-09-28 | 2008-04-03 | Fujifilm Corporation | Écran à émission spontanée, procédé de fabrication d'un écran à émission spontanée, film conducteur transparent, dispositif électroluminescent, électrode transparente de cellule solaire et électrode transparente de papier électronique |
| EP2385425A1 (en) | 2010-05-07 | 2011-11-09 | Fujifilm Corporation | Silver halide photographic light-sensitive material for movie |
| WO2012035314A1 (en) | 2010-09-17 | 2012-03-22 | Fujifilm Manufacturing Europe Bv | Photographic paper |
| CN103396372A (zh) * | 2013-08-09 | 2013-11-20 | 中国科学院南海海洋研究所 | 一类2,5-二酮哌嗪衍生物及其制备方法和在制备抗海洋污损生物防除剂中的应用 |
| WO2021213762A1 (en) | 2020-04-24 | 2021-10-28 | Fujifilm Manufacturing Europe Bv | Photographic paper |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2165421A (en) * | 1936-09-25 | 1939-07-11 | Eastman Kodak Co | Hardening photographic emulsions |
| US2422680A (en) * | 1944-06-01 | 1947-06-24 | Du Pont | Process for preparing hydrophilic color-former silver halide dispersions |
-
0
- BE BE483860D patent/BE483860A/xx unknown
-
1947
- 1947-07-11 US US760488A patent/US2586168A/en not_active Expired - Lifetime
-
1948
- 1948-03-20 GB GB8363/48A patent/GB639097A/en not_active Expired
- 1948-06-23 FR FR968167D patent/FR968167A/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2165421A (en) * | 1936-09-25 | 1939-07-11 | Eastman Kodak Co | Hardening photographic emulsions |
| US2422680A (en) * | 1944-06-01 | 1947-06-24 | Du Pont | Process for preparing hydrophilic color-former silver halide dispersions |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2950197A (en) * | 1955-04-18 | 1960-08-23 | Eastman Kodak Co | Hardening of gelatin |
| US2969392A (en) * | 1957-12-30 | 1961-01-24 | Union Oil Co | Amidomethylation of aromatic hydrocarbons |
| US3128180A (en) * | 1958-07-02 | 1964-04-07 | Eastman Kodak Co | Hardened high-contrast photographic silver chloride emulsions and method of processing |
| US3119825A (en) * | 1961-03-08 | 1964-01-28 | Staley Mfg Co A E | Methylol leucine diketopiperazines |
| US3288775A (en) * | 1961-04-07 | 1966-11-29 | Ciba Ltd | Method of hardening gelatin by reacting with conjugated heterocyclic compounds containing halogen atoms and water-solubilizing acid groups |
| US3372030A (en) * | 1962-12-14 | 1968-03-05 | Pavelle Corp | Method of shortening the processing time of color photography |
| US3380828A (en) * | 1965-08-02 | 1968-04-30 | Eastman Kodak Co | Antistain agents for spectrally sensitized silver halide photographic elements |
| US3649281A (en) * | 1967-10-04 | 1972-03-14 | Fuji Photo Film Co Ltd | Photographic processing for photographic silver halide light-sensitive elements |
| US3775128A (en) * | 1971-08-25 | 1973-11-27 | Fuji Photo Film Co Ltd | Silver halide emulsion containing a triazine as antifoggant |
| JPS491223A (en)) * | 1972-04-17 | 1974-01-08 | ||
| US4009036A (en) * | 1973-12-13 | 1977-02-22 | Agfa-Gevaert A.G. | Photographic developer |
| EP0124795A2 (en) | 1983-04-11 | 1984-11-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion |
| WO2008038764A1 (fr) | 2006-09-28 | 2008-04-03 | Fujifilm Corporation | Écran à émission spontanée, procédé de fabrication d'un écran à émission spontanée, film conducteur transparent, dispositif électroluminescent, électrode transparente de cellule solaire et électrode transparente de papier électronique |
| EP2385425A1 (en) | 2010-05-07 | 2011-11-09 | Fujifilm Corporation | Silver halide photographic light-sensitive material for movie |
| WO2012035314A1 (en) | 2010-09-17 | 2012-03-22 | Fujifilm Manufacturing Europe Bv | Photographic paper |
| CN103396372A (zh) * | 2013-08-09 | 2013-11-20 | 中国科学院南海海洋研究所 | 一类2,5-二酮哌嗪衍生物及其制备方法和在制备抗海洋污损生物防除剂中的应用 |
| CN103396372B (zh) * | 2013-08-09 | 2015-05-20 | 中国科学院南海海洋研究所 | 一类2,5-二酮哌嗪衍生物及其制备方法和在制备抗海洋污损生物防除剂中的应用 |
| WO2021213762A1 (en) | 2020-04-24 | 2021-10-28 | Fujifilm Manufacturing Europe Bv | Photographic paper |
Also Published As
| Publication number | Publication date |
|---|---|
| BE483860A (en)) | |
| FR968167A (fr) | 1950-11-21 |
| GB639097A (en) | 1950-06-21 |
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