US3165410A - Photographic emulsions containing cyclic ketone sensitizers - Google Patents
Photographic emulsions containing cyclic ketone sensitizers Download PDFInfo
- Publication number
- US3165410A US3165410A US113065A US11306561A US3165410A US 3165410 A US3165410 A US 3165410A US 113065 A US113065 A US 113065A US 11306561 A US11306561 A US 11306561A US 3165410 A US3165410 A US 3165410A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- photographic
- emulsion
- emulsions
- sensitizers
- 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
- 239000000839 emulsion Substances 0.000 title claims description 54
- 150000003997 cyclic ketones Chemical class 0.000 title description 2
- 229910052709 silver Inorganic materials 0.000 claims description 37
- 239000004332 silver Substances 0.000 claims description 37
- -1 SILVER HALIDE Chemical class 0.000 claims description 34
- 230000001235 sensitizing effect Effects 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 238000000034 method Methods 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920002301 cellulose acetate Polymers 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 230000029087 digestion Effects 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000282320 Panthera leo Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910021612 Silver iodide Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- 229940045105 silver iodide Drugs 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- LDTXKLFJGAOGQT-UHFFFAOYSA-N 2,4-diacetyl-5-hydroxy-5-methylcyclohexan-1-one Chemical compound C(C)(=O)C1C(CC(C(C1)C(C)=O)=O)(C)O LDTXKLFJGAOGQT-UHFFFAOYSA-N 0.000 description 1
- DXBLIKWIRLTTDK-UHFFFAOYSA-N 3-hydroxy-3-methylcyclohexan-1-one Chemical compound CC1(O)CCCC(=O)C1 DXBLIKWIRLTTDK-UHFFFAOYSA-N 0.000 description 1
- DYKMWPGPJJUGJB-UHFFFAOYSA-N 4,6-diacetyl-3-methylcyclohex-2-en-1-one Chemical compound C(C)(=O)C1C(=CC(C(C1)C(C)=O)=O)C DYKMWPGPJJUGJB-UHFFFAOYSA-N 0.000 description 1
- CRHGSBGMOSDOKP-UHFFFAOYSA-N 6-acetyl-3-methylcyclohex-2-en-1-one Chemical compound CC(=O)C1CCC(C)=CC1=O CRHGSBGMOSDOKP-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 101100295741 Gallus gallus COR4 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 229920002494 Zein Polymers 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 229910052946 acanthite Inorganic materials 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 108091005647 acylated proteins Proteins 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VLTANIMRIRCCOQ-UHFFFAOYSA-N hagemann's ester Chemical compound CCOC(=O)C1CCC(=O)C=C1C VLTANIMRIRCCOQ-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229940056910 silver sulfide Drugs 0.000 description 1
- XUARKZBEFFVFRG-UHFFFAOYSA-N silver sulfide Chemical compound [S-2].[Ag+].[Ag+] XUARKZBEFFVFRG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 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
- G03C1/08—Sensitivity-increasing substances
- G03C1/10—Organic substances
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/487—Saturated compounds containing a keto group being part of a ring containing hydroxy groups
- C07C49/497—Saturated compounds containing a keto group being part of a ring containing hydroxy groups a keto group being part of a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/603—Unsaturated compounds containing a keto groups being part of a ring of a six-membered ring, e.g. quinone methides
Definitions
- This' invention concerns photographic silver halide emulsions, and more particularly, photographic silver halide emulsions containing a novel sensitizing material.
- silver halide emulsions can be chemically sensitized with a variety of materials in order to increase the speed thereof. Certain chemical sensitizers are believed to react with the silver halide to form on the surface of the silver halide minute amounts of silver sulfide, silver, or other noble metals. In addition, other classes of compounds can be utilized to increase the sensitivity of photographic silver halide emulsions that apparently do not enter into chemical combination with the silver halide.
- ketonic sensitizers of the invention are 3-alkyl-3- hydroxycyclohexanones and 3-alkyl-2-cyclohexenones having at least one carbonyl radical attached to the cyclic nucleus, the 4 and 6 positions on the cyclic nucleus being points of attachment for the carbonyl radicals.
- substituents can also be attached to the 5 position on the cyclic nucleus including alkyl, acyl, alkoxy carbonyl, alkoxy, pyridyl etc.
- Preferred ketonic sensitizers of the invention have the formulas R' R B R R R R -O wherein R and R are alkyl radicals having 1 to 6 carbon atoms and wherein R R R and R are hydrogen atoms or carbonyl radicals having the formulas wherein R and R are alkyl radicals having 1 to 6 carbon atoms. At least one of the substituents in the group R and R or R and R is a carbonyl radical.
- Typical alkyl radicals include methyl, ethyl, n-propyl, isopropyl, nbutyl, tert.-butyl, n-phenyl, n-hexyl and the like.
- ketonic addenda of the invention can be added to photographic silver halide emulsions for the purpose of increasing the sensitivity or speed thereof.
- the preparation of photographic silver halide emulsions such as are suitably sensitized with the addenda ofthe invention typically involves three separate operations: (1) emulsification and digestion of silver halide, (2) the freeing of the emulsion of excess water-soluble salts, suitably by washing with water, and (3) the second digestion or after-ripening to obtain increased emulsion speed or sensitivity.
- the sensitizers of our invention can be added to the emulsion before the final digestion or afterripening, or they can be added immediately 'prior to the coating.
- the particular quantity of the present ketonic sensitizers used in a given emulsion ⁇ can vary, depending upon the effects desired, degree of ripening, silver content of the emulsion, etc.
- the amount used is also dependent upon the particular stage at which the sensitizer is added during the preparation of the emulsion. I have found that generally from about .1 to 10 grams per mole of silver halide are quite adequate to accomplish the desired sensitization. Exposure of the treated emulsion in conventional photographic testing apparatus, such as an intensity scale sensitometer, will reveal the most advantageous concentrations for the present ketonic sensitizers in that particular emulsion. Such techniques are well understood by those skilled in the art.
- the sensitizer addenda of the invention can be added to photographic emulsions using any of the well-known techniques in emulsion making.
- the subject sensitizers can be dissolved in a suitable solvent and added to the silver halide emulsion, or they can be added to the emulsion in the form of a dispersion similar'to the technique used to incorporate certain types of color-forming compounds (couplers) in a photographic emulsion.
- Couplers color-forming compounds
- the solvent should be selected so that it has no harmful effect upon the emulsion in accordance with usual practice, and generally solvents or diluents which are miscible with water are to be preferred.
- Water alone is a dispersing medium for some of the sensitizers of the invention.
- the subject sensitizers can be dissolved in solvents, such as ethanol, acetone, pyridine, N,N-dimethylformamide, etc., and added to the emulsion in this form.
- the ketonic sensitizer addenda which have been described can be used in various kinds of photographic emulsions. In addition to being useful in orthochromatic, panchromatic, and infrared sensitive emulsions, they are also useful in X-ray and other nonoptically sensitized emulsions. They can be added to the emulsion before or after any sensitizing dyes which are used.
- Various silver salts can be used as the sensitive salt such as silver bromide, silver iodide, silver chloride, or mixed silver halides such as silver chlorobromide or silver bromoiodide.
- the subject addenda can be used in emulsions intended for color photography, for example, emulsions containing colorforming couplers or emulsions to be developed by solutions containing couplers or other color-generating materials, emulsion of the mixed-packet type, such as described in Godowsky US. Patent 2,698,794, issued January 4, 1955, or emulsions of the mixed-grain type, such as described in Carroll and Hanson US. Patent 2,592,243, issued April 8, 1952.
- ketonic sensitizers can also be used in emulsions which form latent images predominantly on the surface of the silver halide crystals or in emulsions ployed for preparing silver halideemulsions, there can.
- colloids which can be used are polyvinyl alcohol or a hydrolyzed polyvinyl acetate as described in Lowe US. Patent [2,286,215, issued June 16, 1942; a far hydrolyzed cellulose ester such as cellulose acetate hydrolyzed to an acetyl content of 19-26% as described in U.S. Patent 2,327,808, of Lowe and. Clark, issued August 24, 1943; a water-soluble ethanolamine cellulose acetate as described in Yutzy US.
- Patent 2,768,154 issued October 23, 1956; or containing cyano-acetyl groups such asthe vinyl alcohol-vinyl cyano acetate copolymer as described in Unruh, Smith and Priest US. Patent 2,808,331, issued October 1, 1957; or a polymeric material which results from polymerizing a protein or a saturated acylated protein with a monomer having a'vinyl group as described in Illingsworth, Dann and Gates US. Patent 2,852,382, issued September 19, 1958. If desired, compatible mixtures of two or more of these colloids can be employed for dispersing the silver halide in its preparation. of the invention can be coated on a wide variety of supports in accordance with usual practice.
- Typical supports for photographic elements of the invention include cellulose nitrate film, cellulose acetate film, polyvinyl acetal film, polystyrene film, polyethyleneterephthalate film and related films of resinous materials, as well as glass, paper,
- a high speed gelatino-silver halide emulsion panchrorm atically sensitized With a cyanine dye was prepared. The.
- silver halide was composed of 6 molepercent of silver iodide and 94 mole percent of silver bromide.
- the emulsion comprised 245 g. of gelatin per mole of silver halide.
- Several typical ketonic sensitizers of the invention were incorporated in varying amounts in the prepared photographic emulsion.
- the emulsion containing the various sensitizers and control emulsions containing no sensitizer were coated on a cellulose acetate film support at a coverage of 430 mg. ofsilver per square foot.
- Samples The above-described emulsions The results of the sensitomctric tests are summarized by the data set out in the table below.
- the amount of addenda is set out as grams of addenda per mole of silver halide.
- the developer had the following formula:
- the 4,6 diacetyl -'3 hydroxy-3-methylcyclohexanone sensitizer employed in Example 1 was prepared'by the procedure of Knoevnagel disclosed in Chem. Ber., 36, 2136 1903 r r
- the 4,6 diacetyl 3-methyl-2-cyclohexenone sensitizer employed in Example 2 was prepared by dehydrating the sensitizer utilized in Example 1. Thedehydration was effected by passing hydrogen chloride gas into 4,6-diacetyl- 3 -hydroxy-3-methylcyclohexanone in a;reaction vessel in an ice bath until turbidity was observed, and thereafter the reaction mixture was poured into a sodium carbonate.
- V 1 6-acetyl-3-methyl-2-cyclohexenone sensitizer i employed in Example 3, was prepared by the procedure of This sensitizer boiled 7172 C./0.6 mm. and. had an index of refraction of 1.52 71.
- Example 4 employed in Example 4 was prepared by the pyrolytic distillation' of 4,6-dicarbethoxy -3-hydroxy-3-methycyclohexanone which was described by Rabe in Annalen, 332, 1 (1904). This'sensitizer was a pale yellow oil boiling 72 C./0.04 mm., having an index of refraction of n 1.4854 and a carbon and'hydrogen analysis calculated for C10H1403 of: I
- the present invention thus provides newand' useful photographic emulsions, and more particularly, photographicsilver halide emulsions sensitized with a novel class of sensitizers.
- a photographic silver halide emulsion containing a sensitizing amount of a cyclic sensitizing compound having a formula selected from the group-consisting of R1 R2 R R7 and R ' O EL- 0 0e wherein and R arealkyl radicals having 1m 6 car bon atoms, and R R R and R are selected from the group consisting of a hydrogen atom and a carbonyl radical having a formula selected from the group consisting of l u (
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE618139D BE618139A (pt) | 1961-05-29 | ||
| US113065A US3165410A (en) | 1961-05-29 | 1961-05-29 | Photographic emulsions containing cyclic ketone sensitizers |
| FR898458A FR1324000A (fr) | 1961-05-29 | 1962-05-23 | Nouveaux sensibilisateurs photographiques et émulsions contenant ces sensibilisateurs |
| GB20378/62A GB986205A (en) | 1961-05-29 | 1962-05-28 | Photographic silver halide emulsions of increased sensitivity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US113065A US3165410A (en) | 1961-05-29 | 1961-05-29 | Photographic emulsions containing cyclic ketone sensitizers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3165410A true US3165410A (en) | 1965-01-12 |
Family
ID=22347432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US113065A Expired - Lifetime US3165410A (en) | 1961-05-29 | 1961-05-29 | Photographic emulsions containing cyclic ketone sensitizers |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3165410A (pt) |
| BE (1) | BE618139A (pt) |
| GB (1) | GB986205A (pt) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4334010A (en) * | 1980-07-17 | 1982-06-08 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive element |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE557659A (pt) * | 1956-05-21 | |||
| US2373659A (en) * | 1944-10-26 | 1945-04-17 | Eastman Kodak Co | Sensitized photographic emulsion |
| US2887479A (en) * | 1955-11-15 | 1959-05-19 | Eastman Kodak Co | Heterocyclic quaternary salts containing a cyclohexenylidenemethyl substituent |
-
0
- BE BE618139D patent/BE618139A/xx unknown
-
1961
- 1961-05-29 US US113065A patent/US3165410A/en not_active Expired - Lifetime
-
1962
- 1962-05-28 GB GB20378/62A patent/GB986205A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2373659A (en) * | 1944-10-26 | 1945-04-17 | Eastman Kodak Co | Sensitized photographic emulsion |
| US2887479A (en) * | 1955-11-15 | 1959-05-19 | Eastman Kodak Co | Heterocyclic quaternary salts containing a cyclohexenylidenemethyl substituent |
| BE557659A (pt) * | 1956-05-21 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4334010A (en) * | 1980-07-17 | 1982-06-08 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive element |
Also Published As
| Publication number | Publication date |
|---|---|
| BE618139A (pt) | |
| GB986205A (en) | 1965-03-17 |
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