DE1003586B - Verfahren zum Einlagern von Bestandteilen in Gelatine-Halogensilber-Emulsionen, insbesondere fuer farbenphotographische Zwecke, wie Farbbildnern - Google Patents
Verfahren zum Einlagern von Bestandteilen in Gelatine-Halogensilber-Emulsionen, insbesondere fuer farbenphotographische Zwecke, wie FarbbildnernInfo
- Publication number
- DE1003586B DE1003586B DEE11699A DEE0011699A DE1003586B DE 1003586 B DE1003586 B DE 1003586B DE E11699 A DEE11699 A DE E11699A DE E0011699 A DEE0011699 A DE E0011699A DE 1003586 B DE1003586 B DE 1003586B
- Authority
- DE
- Germany
- Prior art keywords
- solvent
- coupler
- water
- solution
- dispersion
- 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.)
- Pending
Links
- 239000000839 emulsion Substances 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 16
- 238000010348 incorporation Methods 0.000 title claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 47
- 239000002904 solvent Substances 0.000 claims description 34
- 239000006185 dispersion Substances 0.000 claims description 26
- -1 silver halide Chemical class 0.000 claims description 23
- 238000009835 boiling Methods 0.000 claims description 20
- 238000010992 reflux Methods 0.000 claims description 19
- 108010010803 Gelatin Proteins 0.000 claims description 15
- 239000008273 gelatin Substances 0.000 claims description 15
- 229920000159 gelatin Polymers 0.000 claims description 15
- 235000019322 gelatine Nutrition 0.000 claims description 15
- 235000011852 gelatine desserts Nutrition 0.000 claims description 15
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- 239000000975 dye Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 6
- 229910052709 silver Inorganic materials 0.000 claims description 6
- 239000004332 silver Substances 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 3
- 235000011152 sodium sulphate Nutrition 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims description 2
- 238000007605 air drying Methods 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 30
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims 5
- 239000004615 ingredient Substances 0.000 claims 5
- 239000000084 colloidal system Substances 0.000 claims 4
- 229910052708 sodium Inorganic materials 0.000 claims 4
- 239000011734 sodium Substances 0.000 claims 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- QVLXDGDLLZYJAM-UHFFFAOYSA-N 2,5-dioctylbenzene-1,4-diol Chemical compound CCCCCCCCC1=CC(O)=C(CCCCCCCC)C=C1O QVLXDGDLLZYJAM-UHFFFAOYSA-N 0.000 claims 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 2
- 239000000470 constituent Substances 0.000 claims 2
- 229960002380 dibutyl phthalate Drugs 0.000 claims 2
- 239000002245 particle Substances 0.000 claims 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims 2
- 239000011877 solvent mixture Substances 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 2
- AYLDJQABCMPYEN-UHFFFAOYSA-N (4-azaniumylphenyl)-diethylazanium;sulfate Chemical compound OS(O)(=O)=O.CCN(CC)C1=CC=C(N)C=C1 AYLDJQABCMPYEN-UHFFFAOYSA-N 0.000 claims 1
- ZZTTYXJJOHFNFS-UHFFFAOYSA-N 1-benzylidene-1-oxo-N,3-diphenyl-4H-1,3-thiazol-4-id-2-imine Chemical compound C(C1=CC=CC=C1)=S1(C(N([C-]=C1)C1=CC=CC=C1)=NC1=CC=CC=C1)=O ZZTTYXJJOHFNFS-UHFFFAOYSA-N 0.000 claims 1
- PMWJOLLLHRDHNP-UHFFFAOYSA-N 2,3-dioctylbenzene-1,4-diol Chemical compound CCCCCCCCC1=C(O)C=CC(O)=C1CCCCCCCC PMWJOLLLHRDHNP-UHFFFAOYSA-N 0.000 claims 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 claims 1
- 208000023514 Barrett esophagus Diseases 0.000 claims 1
- NTZRDKVFLPLTPU-UHFFFAOYSA-N CC[Na] Chemical compound CC[Na] NTZRDKVFLPLTPU-UHFFFAOYSA-N 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 150000003142 primary aromatic amines Chemical class 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 239000003021 water soluble solvent Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 28
- 238000003756 stirring Methods 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 15
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 239000011928 denatured alcohol Substances 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- PTMRDOLOEDPHLB-UHFFFAOYSA-N 2,3-dipentylphenol Chemical compound CCCCCC1=CC=CC(O)=C1CCCCC PTMRDOLOEDPHLB-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 229960001413 acetanilide Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- OHNQVRIYXBIAPC-UHFFFAOYSA-N 2-phenoxy-N-phenylheptanamide Chemical compound C(CCCC)C(C(=O)NC1=CC=CC=C1)OC1=CC=CC=C1 OHNQVRIYXBIAPC-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- WMVJWKURWRGJCI-UHFFFAOYSA-N 2,4-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=C(O)C(C(C)(C)CC)=C1 WMVJWKURWRGJCI-UHFFFAOYSA-N 0.000 description 1
- GIXSFSVVKULPEK-UHFFFAOYSA-N 2,4-dichloro-3-methylphenol Chemical compound CC1=C(Cl)C=CC(O)=C1Cl GIXSFSVVKULPEK-UHFFFAOYSA-N 0.000 description 1
- LNOVILZQNJSJRU-UHFFFAOYSA-N 2-(2,4-dipentylphenoxy)acetic acid Chemical compound CCCCCC1=CC=C(OCC(O)=O)C(CCCCC)=C1 LNOVILZQNJSJRU-UHFFFAOYSA-N 0.000 description 1
- XXRRCDQNGDNYGY-UHFFFAOYSA-N 2-(3,4-dinitrophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1 XXRRCDQNGDNYGY-UHFFFAOYSA-N 0.000 description 1
- FLUYDOVOMDZUEV-UHFFFAOYSA-N 2-(4-nitrophenoxy)acetyl chloride Chemical compound [O-][N+](=O)C1=CC=C(OCC(Cl)=O)C=C1 FLUYDOVOMDZUEV-UHFFFAOYSA-N 0.000 description 1
- QXQMENSTZKYZCE-UHFFFAOYSA-N 2-[2,4-bis(2-methylbutan-2-yl)phenoxy]acetic acid Chemical compound CCC(C)(C)C1=CC=C(OCC(O)=O)C(C(C)(C)CC)=C1 QXQMENSTZKYZCE-UHFFFAOYSA-N 0.000 description 1
- KSYTWDUNKAIFLK-UHFFFAOYSA-N 2-[2,4-bis(2-methylbutan-2-yl)phenoxy]acetyl chloride Chemical compound CCC(C)(C)C1=CC=C(OCC(Cl)=O)C(C(C)(C)CC)=C1 KSYTWDUNKAIFLK-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- SDHQGBWMLCBNSM-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]ethyl acetate Chemical compound COCCOCCOCCOC(C)=O SDHQGBWMLCBNSM-UHFFFAOYSA-N 0.000 description 1
- QDGJHZNOQSIFAT-UHFFFAOYSA-N 2-amino-4-chloro-5-methylphenol Chemical compound CC1=CC(O)=C(N)C=C1Cl QDGJHZNOQSIFAT-UHFFFAOYSA-N 0.000 description 1
- SMFHPCZZAAMJJO-UHFFFAOYSA-N 2-chloro-5-methylphenol Chemical compound CC1=CC=C(Cl)C(O)=C1 SMFHPCZZAAMJJO-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- MCTXOQDMAMSOCX-UHFFFAOYSA-N 2-ethylphenol;hydrochloride Chemical compound Cl.CCC1=CC=CC=C1O MCTXOQDMAMSOCX-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- NIPDVSLAMPAWTP-UHFFFAOYSA-N 2-methoxy-5-nitroaniline Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N NIPDVSLAMPAWTP-UHFFFAOYSA-N 0.000 description 1
- LRUOKTVHUOMJJU-UHFFFAOYSA-N 2-pentyl-2-phenoxyheptanoic acid Chemical compound C(CCCC)C(C(=O)O)(OC1=CC=CC=C1)CCCCC LRUOKTVHUOMJJU-UHFFFAOYSA-N 0.000 description 1
- PJDHCXHEJHLXCI-UHFFFAOYSA-N 3-amino-N-(5-chloro-2-hydroxy-4-methylphenyl)benzamide Chemical compound NC=1C=C(C(=O)NC2=C(C=C(C(=C2)Cl)C)O)C=CC1 PJDHCXHEJHLXCI-UHFFFAOYSA-N 0.000 description 1
- MLQOSNCDCNTIOP-UHFFFAOYSA-N 3-methylphenol;hydrochloride Chemical compound Cl.CC1=CC=CC(O)=C1 MLQOSNCDCNTIOP-UHFFFAOYSA-N 0.000 description 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
- HXUIDZOMTRMIOE-UHFFFAOYSA-M 3-oxo-3-phenylpropionate Chemical compound [O-]C(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-M 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- AVDLFIONKHGQAP-UHFFFAOYSA-N 4-nitrophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1 AVDLFIONKHGQAP-UHFFFAOYSA-N 0.000 description 1
- MYAALGBQWWRACC-UHFFFAOYSA-N 6-oxo-6-(oxolan-2-ylmethoxy)hexanoic acid Chemical compound OC(=O)CCCCC(=O)OCC1CCCO1 MYAALGBQWWRACC-UHFFFAOYSA-N 0.000 description 1
- QVUNMEASSZUQGZ-UHFFFAOYSA-N COC(C(=O)NC1=CC=CC=C1)C(=O)C1=CC(=CC=C1)[N+]([O-])=O Chemical compound COC(C(=O)NC1=CC=CC=C1)C(=O)C1=CC(=CC=C1)[N+]([O-])=O QVUNMEASSZUQGZ-UHFFFAOYSA-N 0.000 description 1
- 101100165177 Caenorhabditis elegans bath-15 gene Proteins 0.000 description 1
- NUBXRBBSBVYJSD-UHFFFAOYSA-N Cl.COCC(=O)NC1=CC=CC=C1 Chemical compound Cl.COCC(=O)NC1=CC=CC=C1 NUBXRBBSBVYJSD-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- JANBFCARANRIKJ-UHFFFAOYSA-N bis(3-methylbutyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCOC(=O)C1=CC=CC=C1C(=O)OCCC(C)C JANBFCARANRIKJ-UHFFFAOYSA-N 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 210000000078 claw Anatomy 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940060367 inert ingredients Drugs 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- ZMYCGFKAPZHNPC-UHFFFAOYSA-N n-methyl-n-(4-methylphenyl)acetamide Chemical compound CC(=O)N(C)C1=CC=C(C)C=C1 ZMYCGFKAPZHNPC-UHFFFAOYSA-N 0.000 description 1
- CIPHTOQKGSLCLV-UHFFFAOYSA-N n-phenylnaphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)NC1=CC=CC=C1 CIPHTOQKGSLCLV-UHFFFAOYSA-N 0.000 description 1
- RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical class CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US476561A US2801171A (en) | 1954-12-20 | 1954-12-20 | Photographic color former dispersions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1003586B true DE1003586B (de) | 1957-02-28 |
Family
ID=23892363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEE11699A Pending DE1003586B (de) | 1954-12-20 | 1955-12-17 | Verfahren zum Einlagern von Bestandteilen in Gelatine-Halogensilber-Emulsionen, insbesondere fuer farbenphotographische Zwecke, wie Farbbildnern |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2801171A (en, 2012) |
| BE (1) | BE543745A (en, 2012) |
| DE (1) | DE1003586B (en, 2012) |
| FR (1) | FR1148474A (en, 2012) |
| GB (1) | GB791219A (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1127714B (de) | 1960-08-20 | 1962-04-12 | Perutz Photowerke G M B H | Verfahren zur Herstellung von farbphotographischen Halogensilberemulsionen |
| DE2733206A1 (de) * | 1976-07-23 | 1978-01-26 | Fuji Photo Film Co Ltd | Farbenfotografisches material |
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2949360A (en) * | 1956-08-31 | 1960-08-16 | Eastman Kodak Co | Photographic color former dispersions |
| US3170791A (en) * | 1961-02-10 | 1965-02-23 | Owens Illinois Glass Co | Process for making a stencil screen coating and composition therefor |
| US3335011A (en) * | 1962-03-23 | 1967-08-08 | Pavelle Corp | Production of stabilized dispersions of color couplers for photographic materials |
| US3271152A (en) * | 1962-09-04 | 1966-09-06 | Eastman Kodak Co | Light-sensitive elements for color photography and process therefor |
| US3379529A (en) * | 1963-02-28 | 1968-04-23 | Eastman Kodak Co | Photographic inhibitor-releasing developers |
| US3297445A (en) * | 1963-04-01 | 1967-01-10 | Eastman Kodak Co | Photographic inhibitor releasing developers |
| US3491235A (en) * | 1964-08-13 | 1970-01-20 | Eastman Kodak Co | Organic scintillating layer in a photographic element |
| US3469987A (en) * | 1965-06-21 | 1969-09-30 | Eastman Kodak Co | Method of spectrally sensitizing photographic silver halide emulsions |
| US3660101A (en) * | 1965-06-21 | 1972-05-02 | Eastman Kodak Co | Photographic materials and processes |
| US3426010A (en) * | 1965-12-01 | 1969-02-04 | Du Pont | Thiazole-pyrazolone azo yellow dyes |
| JPS5547378B2 (en, 2012) * | 1971-09-04 | 1980-11-29 | ||
| JPS527344B2 (en, 2012) * | 1973-07-02 | 1977-03-01 | ||
| BE833512A (fr) * | 1974-09-17 | 1976-03-17 | Nouvelle composition de latex charge par un compose hydrophobe, sa preparation et son application photographique | |
| US4512969A (en) * | 1974-09-17 | 1985-04-23 | Eastman Kodak Company | Compositions containing hydrophobic addenda uniformly loaded in latex polymer particles |
| US4304769A (en) * | 1974-09-17 | 1981-12-08 | Eastman Kodak Company | Process for achieving uniform, efficient distribution of hydrophobic materials through hydrophilic colloid layers and loaded latex compositions |
| JPS5525057A (en) * | 1978-08-10 | 1980-02-22 | Fuji Photo Film Co Ltd | Silver halide photographic material |
| US4214047A (en) * | 1979-05-04 | 1980-07-22 | Eastman Kodak Company | Photographic elements having hydrophilic colloid layers containing hydrophobic addenda uniformly loaded in latex polymer particles |
| JPS5938576B2 (ja) * | 1979-05-07 | 1984-09-18 | コニカ株式会社 | シアン色素画像の形成方法 |
| US4247627A (en) * | 1979-10-10 | 1981-01-27 | Eastman Kodak Company | Photographic elements having hydrophilic colloid layers containing hydrophobic ultraviolet absorbers uniformly loaded in latex polymer particles |
| JPS5699341A (en) * | 1980-01-11 | 1981-08-10 | Konishiroku Photo Ind Co Ltd | Forming method for cyan dye image |
| JPS56116030A (en) * | 1980-01-14 | 1981-09-11 | Konishiroku Photo Ind Co Ltd | Forming method for cyan dye image |
| JPS56126830A (en) * | 1980-03-11 | 1981-10-05 | Konishiroku Photo Ind Co Ltd | Silver halide photographic sensitive material |
| JPS59188641A (ja) | 1983-04-11 | 1984-10-26 | Fuji Photo Film Co Ltd | ハロゲン化銀写真乳剤 |
| JPS61251852A (ja) | 1985-04-30 | 1986-11-08 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀カラ−写真感光材料の処理方法 |
| US4725529A (en) | 1985-04-30 | 1988-02-16 | Konishiroku Photo Industry Co., Ltd. | Developing inhibitor arrangment in light-sensitive silver halide color photographic materials |
| JPS61255342A (ja) | 1985-05-09 | 1986-11-13 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| AU588878B2 (en) | 1985-05-31 | 1989-09-28 | Konishiroku Photo Industry Co., Ltd. | Method for forming direct positive color image |
| JPH0711695B2 (ja) | 1985-09-25 | 1995-02-08 | 富士写真フイルム株式会社 | 撮影用ハロゲン化銀カラー感光材料の処理方法 |
| AU591540B2 (en) | 1985-12-28 | 1989-12-07 | Konishiroku Photo Industry Co., Ltd. | Method of processing light-sensitive silver halide color photographic material |
| JPH0677141B2 (ja) | 1986-01-20 | 1994-09-28 | コニカ株式会社 | ハロゲン化銀カラ−写真感光材料 |
| JPH0642043B2 (ja) * | 1986-04-10 | 1994-06-01 | 富士写真フイルム株式会社 | 固体粒子膜の形成方法 |
| JPH06105346B2 (ja) | 1986-11-07 | 1994-12-21 | 富士写真フイルム株式会社 | ハロゲン化銀カラ−写真感光材料の処理方法 |
| JPH0833628B2 (ja) | 1987-12-15 | 1996-03-29 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
| US4885234A (en) * | 1988-09-29 | 1989-12-05 | Eastman Kodak Company | Photographic materials containing stable cyan coupler formulations |
| US5008179A (en) * | 1989-11-22 | 1991-04-16 | Eastman Kodak Company | Increased activity precipitated photographic materials |
| DE69031679T2 (de) | 1989-12-29 | 1998-06-04 | Fuji Photo Film Co Ltd | Farbphotographisches Silberhalogenidmaterial, das einen gelb gefärbten Cyan-Kuppler enthält |
| DE69127002T2 (de) | 1990-01-31 | 1997-11-20 | Fuji Photo Film Co Ltd | Farbphotographisches Silberhalogenidmaterial |
| JPH04445A (ja) | 1990-04-17 | 1992-01-06 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料の処理方法 |
| EP0458131B1 (en) | 1990-05-09 | 1997-08-06 | Fuji Photo Film Co., Ltd. | Photographic processing composition and processing method using the same |
| EP0476327B1 (en) | 1990-08-20 | 1999-11-17 | Fuji Photo Film Co., Ltd. | Data-retainable photographic film product and process for producing color print |
| EP0562476B1 (en) | 1992-03-19 | 2000-10-04 | Fuji Photo Film Co., Ltd. | Method for preparing a silver halide photographic emulsion |
| EP0563708B1 (en) | 1992-03-19 | 2000-06-21 | Fuji Photo Film Co., Ltd. | Process for preparing a silver halide photographic emulsion |
| JP2777949B2 (ja) | 1992-04-03 | 1998-07-23 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
| JP3101848B2 (ja) | 1992-05-15 | 2000-10-23 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
| EP0574090A1 (en) | 1992-06-12 | 1993-12-15 | Eastman Kodak Company | One equivalent couplers and low pKa release dyes |
| US5407791A (en) | 1993-01-18 | 1995-04-18 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| CA2113288A1 (en) * | 1993-01-29 | 1994-07-30 | Kan Takamine | Process for producing aromatic amide compounds |
| DE69424983T2 (de) | 1993-11-24 | 2000-10-19 | Fuji Photo Film Co., Ltd. | Photographische Verarbeitungszusammensetzung und Verarbeitungsverfahren |
| US5545514A (en) * | 1994-07-14 | 1996-08-13 | Konica Corporation | Silver halide light-sensitive color photographic material |
| DE4433637A1 (de) | 1994-09-21 | 1996-03-28 | Agfa Gevaert Ag | Farbfotografisches Silberhalogenidmaterial |
| JPH08104821A (ja) * | 1994-10-03 | 1996-04-23 | Fuji Photo Film Co Ltd | ヒダントイン置換アシルアセトアニリド化合物及びその製造方法 |
| US5476760A (en) | 1994-10-26 | 1995-12-19 | Eastman Kodak Company | Photographic emulsions of enhanced sensitivity |
| EP0711804A3 (de) | 1994-11-14 | 1999-09-22 | Ciba SC Holding AG | Kryptolichtschutzmittel |
| US5585230A (en) * | 1995-03-23 | 1996-12-17 | Eastman Kodak Company | Cyan coupler dispersion with improved stability |
| GB9517912D0 (en) * | 1995-09-02 | 1995-11-01 | Kodak Ltd | Improved oil-in-water emulsions |
| JPH09152696A (ja) | 1995-11-30 | 1997-06-10 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| JP3383499B2 (ja) | 1995-11-30 | 2003-03-04 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
| JP3584119B2 (ja) | 1996-04-05 | 2004-11-04 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
| US5726003A (en) * | 1996-08-15 | 1998-03-10 | Eastman Kodak Company | Cyan coupler dispersion with increased activity |
| US6420103B1 (en) | 1999-03-10 | 2002-07-16 | Eastman Kodak Company | Photographic element |
| ES2219332T3 (es) | 1999-04-30 | 2004-12-01 | Ube Industries, Ltd. | Compuestos de benzoxazol, procedimiento de elaboracion de estos y herbicidas. |
| US6525115B2 (en) | 2000-12-05 | 2003-02-25 | Eastman Kodak Company | Method of making an aqueous dispersion of particles comprising an epoxy material for use in coatings |
| US6509500B2 (en) | 2001-05-24 | 2003-01-21 | Eastman Chemical Company | Continuous preparation of incorporated photographic amides |
| US7338756B2 (en) * | 2003-10-24 | 2008-03-04 | Eastman Kodak Company | Method of preparation of direct dispersions of photographically useful chemicals |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE470936A (en, 2012) * | 1940-02-24 | |||
| US2478400A (en) * | 1945-08-17 | 1949-08-09 | Eastman Kodak Co | Silver halide photographic emulsion with developer and color coupler dispersed therein |
| US2699794A (en) * | 1952-08-22 | 1955-01-18 | Potter Lorraine | Safety canopy for cribs |
-
0
- BE BE543745D patent/BE543745A/xx unknown
-
1954
- 1954-12-20 US US476561A patent/US2801171A/en not_active Expired - Lifetime
-
1955
- 1955-11-09 GB GB31990/55A patent/GB791219A/en not_active Expired
- 1955-12-17 DE DEE11699A patent/DE1003586B/de active Pending
- 1955-12-19 FR FR1148474D patent/FR1148474A/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1127714B (de) | 1960-08-20 | 1962-04-12 | Perutz Photowerke G M B H | Verfahren zur Herstellung von farbphotographischen Halogensilberemulsionen |
| DE2733206A1 (de) * | 1976-07-23 | 1978-01-26 | Fuji Photo Film Co Ltd | Farbenfotografisches material |
Also Published As
| Publication number | Publication date |
|---|---|
| US2801171A (en) | 1957-07-30 |
| FR1148474A (fr) | 1957-12-10 |
| GB791219A (en) | 1958-02-26 |
| BE543745A (en, 2012) |
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