JPS6021048A - Silver halide photosensitive material - Google Patents
Silver halide photosensitive materialInfo
- Publication number
- JPS6021048A JPS6021048A JP12823083A JP12823083A JPS6021048A JP S6021048 A JPS6021048 A JP S6021048A JP 12823083 A JP12823083 A JP 12823083A JP 12823083 A JP12823083 A JP 12823083A JP S6021048 A JPS6021048 A JP S6021048A
- Authority
- JP
- Japan
- Prior art keywords
- group
- silver halide
- mercaptan
- coupler
- grains
- 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.)
- Granted
Links
- -1 Silver halide Chemical class 0.000 title claims abstract description 117
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 54
- 239000004332 silver Substances 0.000 title claims abstract description 54
- 239000000463 material Substances 0.000 title claims abstract description 28
- 239000000839 emulsion Substances 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 239000010419 fine particle Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 7
- 238000005192 partition Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 11
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract description 10
- 238000012545 processing Methods 0.000 abstract description 9
- 125000003118 aryl group Chemical group 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 5
- 206010070834 Sensitisation Diseases 0.000 abstract description 4
- 238000002845 discoloration Methods 0.000 abstract description 4
- 230000008313 sensitization Effects 0.000 abstract description 4
- 238000009826 distribution Methods 0.000 abstract description 3
- 230000006641 stabilisation Effects 0.000 abstract description 3
- 238000011105 stabilization Methods 0.000 abstract description 3
- 238000003860 storage Methods 0.000 abstract description 3
- 239000007844 bleaching agent Substances 0.000 abstract description 2
- 238000000354 decomposition reaction Methods 0.000 abstract description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- 230000007774 longterm Effects 0.000 abstract 1
- 238000004383 yellowing Methods 0.000 abstract 1
- 239000004816 latex Substances 0.000 description 21
- 229920000126 latex Polymers 0.000 description 21
- 238000000034 method Methods 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 20
- 108010010803 Gelatin Proteins 0.000 description 18
- 229920000159 gelatin Polymers 0.000 description 18
- 239000008273 gelatin Substances 0.000 description 18
- 235000019322 gelatine Nutrition 0.000 description 18
- 235000011852 gelatine desserts Nutrition 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 239000000975 dye Substances 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000011161 development Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000010186 staining Methods 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000004442 acylamino group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical group CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical group O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 238000003672 processing method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 125000000565 sulfonamide group Chemical group 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- YKUDHBLDJYZZQS-UHFFFAOYSA-N 2,6-dichloro-1h-1,3,5-triazin-4-one Chemical compound OC1=NC(Cl)=NC(Cl)=N1 YKUDHBLDJYZZQS-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- MXLQAWXKAKUDHC-UHFFFAOYSA-N 2-methyl-n-(5-oxo-1-phenyl-4h-pyrazol-3-yl)prop-2-enamide Chemical compound O=C1CC(NC(=O)C(=C)C)=NN1C1=CC=CC=C1 MXLQAWXKAKUDHC-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical group NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000004422 alkyl sulphonamide group Chemical group 0.000 description 2
- 125000005116 aryl carbamoyl group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 125000005670 ethenylalkyl group Chemical group 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- NPKFETRYYSUTEC-UHFFFAOYSA-N n-[2-(4-amino-n-ethyl-3-methylanilino)ethyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCN(CC)C1=CC=C(N)C(C)=C1 NPKFETRYYSUTEC-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229930003799 tocopherol Natural products 0.000 description 2
- 239000011732 tocopherol Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical compound ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OZFIGURLAJSLIR-UHFFFAOYSA-N 1-ethenyl-2h-pyridine Chemical compound C=CN1CC=CC=C1 OZFIGURLAJSLIR-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- ZFYKDNCOQBBOST-UHFFFAOYSA-N 1-phenylbut-3-en-1-one Chemical compound C=CCC(=O)C1=CC=CC=C1 ZFYKDNCOQBBOST-UHFFFAOYSA-N 0.000 description 1
- ZAVBRLRYUKSUSD-UHFFFAOYSA-N 12-butylhexadecan-1-amine Chemical compound CCCCC(CCCC)CCCCCCCCCCCN ZAVBRLRYUKSUSD-UHFFFAOYSA-N 0.000 description 1
- KPVMVJXYXFUVLR-UHFFFAOYSA-N 12-ethyltetradecan-1-amine Chemical compound CCC(CC)CCCCCCCCCCCN KPVMVJXYXFUVLR-UHFFFAOYSA-N 0.000 description 1
- LZFZQYNTEZSWCP-UHFFFAOYSA-N 2,6-dibutyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC(CCCC)=C1O LZFZQYNTEZSWCP-UHFFFAOYSA-N 0.000 description 1
- ZUAURMBNZUCEAF-UHFFFAOYSA-N 2-(2-phenoxyethoxy)ethanol Chemical compound OCCOCCOC1=CC=CC=C1 ZUAURMBNZUCEAF-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- WEULJWIQMLXOOU-UHFFFAOYSA-N 2-(4-amino-n-ethyl-3-methoxyanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(N)C(OC)=C1 WEULJWIQMLXOOU-UHFFFAOYSA-N 0.000 description 1
- QTLHLXYADXCVCF-UHFFFAOYSA-N 2-(4-amino-n-ethyl-3-methylanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(N)C(C)=C1 QTLHLXYADXCVCF-UHFFFAOYSA-N 0.000 description 1
- WFXLRLQSHRNHCE-UHFFFAOYSA-N 2-(4-amino-n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(N)C=C1 WFXLRLQSHRNHCE-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-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
- 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 1
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- 125000002813 thiocarbonyl group Chemical group *C(*)=S 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
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 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
- 239000001993 wax Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-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
- G03C7/32—Colour coupling substances
- G03C7/36—Couplers containing compounds with active methylene groups
- G03C7/38—Couplers containing compounds with active methylene groups in rings
- G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Abstract
Description
【発明の詳細な説明】
ｆａｌ 発明の技術分野
本発明はハロゲン化銀写真感光材料に関し、さらに詳し
く（マ、ピラゾロン母核を営むマゼンタカプラーを含む
写真材料を発色現像処理することにより最終的に得られ
る非発色部（以下白地という）に発生する黄色等の変色
の程度が改良さ、Ｔｌた／・ロゲン化銀写真感光材料に
関する。Detailed Description of the Invention fal Technical Field of the Invention The present invention relates to a silver halide photographic light-sensitive material, and more particularly, it relates to a silver halide photographic material that is finally obtained by color development processing of a photographic material containing a magenta coupler having a pyrazolone core. This invention relates to a Tl/silver halide photographic light-sensitive material which has an improved degree of discoloration such as yellow that occurs in non-color-developing areas (hereinafter referred to as white background).
（ｂｌ 先行技術とその問題点
ハロゲン化銀写真感光材料は像様露光された後、芳香族
第一級アミン化合物を用いて現像され、生成したアミン
の酸化生成物とカプラーとの反応により色素画像に形成
される。この方法においては、通常イエロー、ｆゼンタ
、シアンの色素画像を形成するためにそれぞれアシルア
セトアミドもしくはベンゾイルメタン系カプラー及びピ
ラゾロン、シアノアセチルもしくはインダシロン系カプ
ラー及びフェノールもしくはナフトール系カプラーが用
いらイする。(bl Prior art and its problems) Silver halide photographic materials are imagewise exposed and then developed using an aromatic primary amine compound, and a dye image is formed by the reaction of the oxidation product of the amine formed with a coupler. In this method, acylacetamide or benzoylmethane couplers and pyrazolone, cyanoacetyl or indasilone couplers and phenol or naphthol couplers are used to form yellow, f-zenta and cyan dye images, respectively. I get annoyed.
得られた色素画１逮は発色現像主薬の酸化生成物とカプ
ラーとの反応によって形成されたアゾメチン色素または
インドアニリン色素から成る。The resulting dye image consists of an azomethine or indoaniline dye formed by the reaction of the oxidation product of a color developing agent with a coupler.
このようにして得らイ′シたカラー写真画像は通常記録
として長期保存されたり、あるいは展示さｎたすするが
、この色糸画像の非発色部、すなわち白地＆１ ′）′
ｅ 、熱、湿度に対して必ずしも安定なものではなく、
長時間ブＣにさらしたり、高温多湿下に保存したりリー
ると白地の変色（以下スティンという）を引き起こし、
画質の劣化をきたすことがある０
ハロゲン化銀写真感光材料が露光、処理後長時間光にさ
らさイしたり、高温多湿下で保存、展示さイしたりする
と白地が黄変する現象はよく知られている。The color photographic images obtained in this way are usually stored for a long time as records or exhibited, but the non-colored parts of the colored images, that is, the white background &1')'
e, is not necessarily stable against heat and humidity,
If exposed to heat or humidity for a long time, or stored under high temperature and humidity, it may cause discoloration of the white background (hereinafter referred to as stain).
It is well known that the white background of silver halide photographic light-sensitive materials turns yellow when exposed to light for a long time after exposure or processing, or when stored or displayed under high temperature and humidity. It is being
この現象は主としてノーロダン化銀写真感光材料中に含
ま几ているマゼンタカプラーの分解によるものとされて
おり、また、Ｊ、Ａ、Ｐ、Ｓ、互、 ２００ （１９７
９）において、Ｒ，Ｊ、 Ｔｕｉｔｅ はスティンがマ
ゼンタカプラーを出発原料として生成さ７１．ることを
報告している。This phenomenon is said to be mainly caused by the decomposition of the magenta coupler contained in the non-rodunized silver photographic light-sensitive material, and is also reported in J.A.P.S., 200 (197
In 9), R, J, Tuite is produced by Stine using a magenta coupler as a starting material 71. It is reported that
従来よりスティンを防止する具体的な方法としては、光
や高温多湿下で分解を起こしにくいマゼンタカプラーの
開発や白地のスティンを防止する化合物の探索が検討さ
れてきた。光や高温多湿下で分解を起こしにくいマゼン
タカプラーの開発は、種々検討されているが、他の写真
性能（例えば発色性、生成した色素の吸収波長等）をも
すべてを満足するマゼンタカプラーの開発は困難であり
、まだ実際に開発されていないのが実情である０またス
ティンを防止する化合物として従来から知らｎている化
合物の例としては抗酸化剤があり、例えば２．５−ジル
ｔ−ブチルハイドロキノンを始めとするハイドロキノン
訪導体、２，６−ジー１−ブチル−ｐ−クレゾール、４
．４’−メチレンビス（２，６−ジーｔ−ブチルフェノ
ール）、２，２１−メチレンビス（４−エチル−６−ｔ
−プｆルフェノール）、４．４’−イソプロピリデンジ
フェノールナトのフェノール訪導体及びトコフェロール
ナトの化合物がある。こｉｔらハイドロキノン訪導体、
フェノール訪導体およびトコフェロールなどの化合物は
、光によるスティンに対しては有効であるが、湿層、熱
ｌこよるスティンに対しては実質的に効果が）τかつｆ
こ０
本発明者の知るかぎりでは、湿熱スティンを有効に防止
する適”４７．１化会物は未だ出現していないのが現状
である。As specific methods for preventing staining, research has been conducted to develop magenta couplers that are less likely to decompose under light or high temperature and humidity, and to search for compounds that prevent staining on white backgrounds. Various studies have been conducted to develop a magenta coupler that does not easily decompose under light or high temperature and humidity, but the development of a magenta coupler that also satisfies all other photographic properties (e.g. color development, absorption wavelength of the produced dye, etc.) is in progress. The fact is that it is difficult to prevent staining and has not yet been actually developed.In addition, antioxidants are examples of compounds that have been known to prevent staining. Hydroquinone visiting conductors including butylhydroquinone, 2,6-di-1-butyl-p-cresol, 4
．． 4'-methylenebis(2,6-di-t-butylphenol), 2,21-methylenebis(4-ethyl-6-t
-polyphenol), 4,4'-isopropylidenediphenol nato phenol conductor, and tocopherol nato compounds. These are hydroquinone conductors,
Compounds such as phenolic conductors and tocopherols are effective against light-induced staining, but have virtually no effect on wet layer, heat-induced staining).
To the best of the present inventor's knowledge, the current situation is that no compound suitable for effectively preventing moist heat staining has yet appeared.
ｆｃ） 発明の目的
従って、不弁明の目的はハロゲン化銀写真感光羽村の非
うら色１ｚμ（白地）が尚温多湿下で長期間保存、展示
さイーシてもへ色等の変色を生起する程度が改善された
マゼンタカプラー含、有ハロゲン化銀写ｌ（感光月料を
提供することにある。fc) Purpose of the Invention Accordingly, the purpose of the invention is to prevent silver halide photographic photosensitive Hamura's non-purple color 1zμ (white background) from causing discoloration such as dark yellow when stored and exhibited for a long period of time under hot and humid conditions. An object of the present invention is to provide a magenta coupler-containing, silver halide photosensitive material with improved properties.
本発明のｒｊｉＪ記目的は、支持体上に少なくとも１層
のマゼンタカプラーが含有されている親油性微粒子を分
散した）・ロゲン化銀乳剤ノーを有するノＡロゲン化銀
写真感元材料において、前記親油性微粒子中にメルカプ
タン化合物を含有することζこより達成されることを見
い出し本発明”ｃ％成するに至った。The object of the present invention is to provide a silver halide photographic material having a silver halide emulsion (in which lipophilic fine particles containing at least one layer of magenta coupler are dispersed on a support). They have discovered that this can be achieved by containing a mercaptan compound in lipophilic fine particles, and have come to form the present invention.
（ｄ） 発明の具体的構成
以下本発明について更に詳細に述べるが、以下の記載は
本発明の範囲を制限するものではない。(d) Specific Structure of the Invention The present invention will be described in more detail below, but the following description is not intended to limit the scope of the present invention.
本発明において用いら７’Ｌる好ましいマゼンタカプラ
ーとしては、下記一般式（ＩＡ）で表わされるマゼンタ
カプラーである。A preferred magenta coupler used in the present invention is a magenta coupler represented by the following general formula (IA).
ｒ１
式中Ａｒｌはフェニル基を表わし、このフェニル基は置
換基を有していてもよい。置換基としては、アルキル基
（例えばメチル基、エチル基など）、アルコキシ基（例
えばメトキシ基、エトキシ基なト）、アリールオキシ基
（例えばフェニルオキシ基など）、アルコキシカルボニ
ル基（例えばメトキシカルボニル基など）、アシルアミ
ノ基（例エバアセチルアミノ基など）、カルバモイル＆
、アルキルカルバモイル基（例工ばメチルカルバモイル
基、エチルカルバモイル基など）、ジアルキ／’ ：／
Ｊ ルハモイル＆ （例、ｊハシメチルカルバモイル基
など）、アリールカルバモイル基（例えばフェニルカル
バモイル法ナト） 、アルキルスルホニル茫（例えはメ
チルスルホニル基）、アリールスルホ＝ ルＭ（例、ｊ
はフェニルスルホニル基）、アルキルスルホンアミド基
（例んばメタンスルホンアミド基）、アルキルスルホン
アミド基（例えばフェニルスルホンアミド基）、スルフ
ァモイル基、アルキルスルファモイル基（例えばエチル
スルファモイル基）、ジアルキルスルファモイル基（例
んばジメチルスルファモイル基）、アルキルチオ基（例
んばメチルチオ基）、アリールチオ基（例えばフェニル
チオ基）、シアノ基、ニトロ基、ハロゲン原子（例えば
フッ素原子、塩素原子、臭素原子など）が挙げら７１．
、この１直換基が２個以上あるときは同じであっても異
なっていてもよい。r1 In the formula, Arl represents a phenyl group, and this phenyl group may have a substituent. Examples of substituents include alkyl groups (e.g., methyl group, ethyl group, etc.), alkoxy groups (e.g., methoxy group, ethoxy group, etc.), aryloxy groups (e.g., phenyloxy group, etc.), alkoxycarbonyl groups (e.g., methoxycarbonyl group, etc.). ), acylamino group (e.g. evaacetylamino group, etc.), carbamoyl &
, alkylcarbamoyl group (for example, methylcarbamoyl group, ethylcarbamoyl group, etc.), dialkyl/' :/
J ruhamoyl & (e.g., j-hashimethylcarbamoyl group, etc.), arylcarbamoyl group (e.g., phenylcarbamoyl group), alkylsulfonyl group (e.g., methylsulfonyl group), arylsulfol M (e.g., j
(phenylsulfonyl group), alkylsulfonamide group (e.g. methanesulfonamide group), alkylsulfonamide group (e.g. phenylsulfonamide group), sulfamoyl group, alkylsulfamoyl group (e.g. ethylsulfamoyl group), dialkyl group Sulfamoyl group (e.g. dimethylsulfamoyl group), alkylthio group (e.g. methylthio group), arylthio group (e.g. phenylthio group), cyano group, nitro group, halogen atom (e.g. fluorine atom, chlorine atom, bromine atom) atoms, etc.) are listed as 71.
, when there are two or more of this one direct substituent, they may be the same or different.
好ましい１１ｍ基としては、ハロゲン原子、アルキル基
、アルコキシ基、アルコキシカルボニル基、シアノ基が
挙げらｎｌそしてＡｒのオルト位の少なくとも１つがハ
ロゲン原子、アルキル基、アルコキシ基によって置換さ
イ’しているものが特に有用である。Preferred 11m groups include halogen atoms, alkyl groups, alkoxy groups, alkoxycarbonyl groups, and cyano groups, where at least one of the ortho positions of nl and Ar is substituted with a halogen atom, an alkyl group, or an alkoxy group. are particularly useful.
Ｙｌは水素原子、ハロゲン原子またはアルコキシ基を表
わし、ハロゲン原子としては塩素原子、臭素原子または
フッ素原子が挙げられるが好ましくは塩素原子である。Yl represents a hydrogen atom, a halogen atom, or an alkoxy group, and examples of the halogen atom include a chlorine atom, a bromine atom, and a fluorine atom, but a chlorine atom is preferred.
またアルコキシ基としては、低級アルコキシ基、例えば
炭素原子数１〜４のアルコキシ基であり、好ましくはメ
トキシ基であるＯ
Ａは−ＮＨ−１−ＮＨＣＯ−または−Ｎ ＨＣＯＮ ｎ
−（但し、窒素原子はピラゾロン環の炭素原子に結合
している。）を表わすＯ
Ｂ１は、カプラーがハロゲン化銀写真感光材料に塗布さ
れている層から当該カプラーを実質的に非拡散性になら
しめるに十分な分子の大きさと形状を有するバラスト基
を表４つじ、このパラスト基としては、炭素原子数が８
以上、好ましくは炭素原子数８〜３２ のアルキル基又
はアリール基であるＯ
Ｚｉ は、水素原子または発色現像主薬とカップリング
反応した後、離脱可能なスプリットオフ基を表わし、ス
プリントオフ基としては、この技術分野において公知の
任意のスプリットオフ基を用いることができ、代表的な
基としては、例えばハロゲン原子、アルコキシ基、了り
−ルオキシ基、ヘテロシクリルオキシ塞、スルホニルオ
キシ基、アシルオキシ基、アシル基、ヘテロシクリル基
、チアンアノ基、アルキルチオ基、アリールチ、オ基−
ヘテロシクリルチオ基、スルホンアミド基、ホスホニル
オキシ基およびアリールアゾ基等が含まれる。Further, the alkoxy group is a lower alkoxy group, for example, an alkoxy group having 1 to 4 carbon atoms, preferably a methoxy group. OA is -NH-1-NHCO- or -NHCON n
- (However, the nitrogen atom is bonded to the carbon atom of the pyrazolone ring.) OB1 represents a method in which the coupler is substantially non-diffusible from the layer in which the coupler is coated on the silver halide photographic light-sensitive material. Table 4 shows ballast groups with sufficient molecular size and shape for smoothing.
As mentioned above, O Zi, which is preferably an alkyl group or an aryl group having 8 to 32 carbon atoms, represents a split-off group that can be separated after a coupling reaction with a hydrogen atom or a color developing agent. Any split-off group known in the art can be used, and representative groups include, for example, a halogen atom, an alkoxy group, an aryloxy group, a heterocyclyloxy group, a sulfonyloxy group, an acyloxy group, an acyl group. , heterocyclyl group, thianano group, alkylthio group, arylthio group, -
Included are a heterocyclylthio group, a sulfonamide group, a phosphonyloxy group, an arylazo group, and the like.
本発明の別の好ましい態様では、下記一般式（ＩＢ）で
表わされるマゼンタカプラーが用いられる一般式〔ＩＢ
〕
２
Ａｒ２
Ａｒ２ ｒ Ｙ２１’ＡおよびＢ２はそ不りぞイを前記
一般式［ＩＡＩのＡｒｓ ｒ Ｙｌ ＋ ＡおよびＢ１
で定義し１こものと同じである。In another preferred embodiment of the present invention, a magenta coupler represented by the following general formula (IB) is used.
] 2 Ar2 Ar2 r Y21'A and B2 are represented by the above general formula [IAI's Ars r Yl + A and B1
It is defined as 1 and is the same as 1.
Ｒ１は水素原子または芳香族環を表わし、前記芳香族環
としてはフェニル基またはフェニレン基が好ましい。R1 represents a hydrogen atom or an aromatic ring, and the aromatic ring is preferably a phenyl group or a phenylene group.
ｍは１才たは２の整数、ｎは２または４の振数をそれぞ
れ表わし、そしてｍが１のときはｎが２１ｍが２のとき
はｎが４をボすが、ｍか２のときはＲ１は芳香族環、特
にフェニレン基を表わすのが好ましい。m is an integer of 1 or 2, n represents a frequency of 2 or 4, respectively, and when m is 1, n is 21. When m is 2, n is 4, but when m or 2. R1 preferably represents an aromatic ring, especially a phenylene group.
前記一般式（ＩＡＩまたは（ＩＢ）で表ゎさイｌ、るマ
ゼンタカプラーの代表的なものとしては下記のものが挙
げらイ１．るが、本発明はこイ１．に限足さイ１．るも
のではない。Typical magenta couplers represented by the general formula (IAI or (IB)) include the following. However, the present invention is limited to these. 1. It is not something that can be done.
（例示マゼンタカプラー）
Ｍｌ −Ｊ
Ｍｌ−２
１−３
Ｍｌ−４
Ｍ１＝５
Ｍｌ−６
１
Ｍｌ−７
ＣＩ！
１
Ｍｌ−８
１
Ｍｌ−９
Ｍｌ−１０
Ｍ １−１１
１
Ｍｌ−１２
ＣＩ！
１−１３
１−１４
１−１５
Ｍ １−１６
Ｍｌ−１７
Ｍ ｌ −１８
１−１９
Ｍ １−２０
Ｍ １−２１
Ｍ １−２２
Ｍ ｌ−２３
Ｍｌ−２４
Ｍ １−２５
Ｍ １−２６
Ｍ １−２７
Ｍｌ−３０
Ｍｌ−３１
Ｍ ｌ −３２
Ｍニー３４
Ｍｌ−４２
以下余Ｅ
本発明の別の好ましい実施態様では、下記一般式［１）
で表わされる単量体カプラーより醒導される繰り返し単
位を有する重合体あるいはこの単量体と、芳香族−級ア
ミン現像王桑と酸化カップリングする能力を持たない少
なくとも１個のエチレン基を有する非発色性単量体（以
下コモノマーという。）の１種以上との共亜合体からな
るマゼンタポリマーカプラーラテックスが用いらイする
。(Exemplary magenta coupler) Ml -J Ml-2 1-3 Ml-4 M1=5 Ml-6 1 Ml-7 CI! 1 Ml-8 1 Ml-9 Ml-10 M 1-11 1 Ml-12 CI! 1-13 1-14 1-15 M 1-16 Ml-17 M l -18 1-19 M 1-20 M 1-21 M 1-22 M l-23 Ml-24 M 1-25 M 1-26 M 1-27 Ml-30 Ml-31 M l -32 M knee 34 Ml-42 In another preferred embodiment of the present invention, the following general formula [1]
A polymer having a repeating unit derived from a monomeric coupler represented by the formula or this monomer and at least one ethylene group that does not have the ability to oxidatively couple with an aromatic-grade amine development mulberry A magenta polymer coupler latex composed of a copolymer with one or more non-chromogenic monomers (hereinafter referred to as comonomers) is used.
Ａｒ３
式中、Ｒ２は水素原子、炭素数１〜４個の低級アルキル
基、才たは塩素原子を表わす。Ar3 In the formula, R2 represents a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or a chlorine atom.
Ａは−ＣＯＮＨ−、−ＮＨ−、−ＮＨＣＯＮＨ−または
−ＮＨＣＯＯ−の２価の結合基を表わす。（但し結合基
の右側の鼠素原子または酸素原子はピラゾロン環の炭素
原子に結合している。）
わす。A represents a divalent bonding group of -CONH-, -NH-, -NHCONH- or -NHCOO-. (However, the mouse atom or oxygen atom on the right side of the bonding group is bonded to the carbon atom of the pyrazolone ring.)
Ｆは炭素数１〜１０個のアルキレン基またはフェニレン
基を表わし、このアルキレン基は直鎖でも分岐していて
もよい。（例えば、メチレン、メチルメチレン、ジメチ
ルメチレン、ジメチレン、トリメチレン、デカメチレン
など。）更にこのアルキレン基はアルキル以外の置換基
によって置換されていてもよい。前記フェニレン基は置
換基を有していてもよい。F represents an alkylene group or phenylene group having 1 to 10 carbon atoms, and this alkylene group may be linear or branched. (For example, methylene, methylmethylene, dimethylmethylene, dimethylene, trimethylene, decamethylene, etc.) Furthermore, this alkylene group may be substituted with a substituent other than alkyl. The phenylene group may have a substituent.
Ｆで表わさイするアルキレン基またはフェニレン基の１
汽換ｐ＋＝とじては、アリール基（例えばフェニル基）
、ニトロ藷、水酸基、シアン基、スルホ基、アルコキシ
基Ｎ３１．ｔばメトキシ基）、アリールオキシ基（例ん
ばフェノキシ基）、アシルオキシ基（例えばアセトキシ
基）、アシルアミノ基（例えばアセチルアミノ基）、ス
ル、ホンアミド基（例エハメタンスル不ンアミド！！！
、）、スルファモイル＆（ｆｌｌｉｆメチルスルファモ
イル基）、ハロケン原子（例んばフッ系原子、塩素原子
、臭素原子など）、カルボキシ基、カルバモイル基（例
えばメチルカルバモイル基）、アルコキシカルボニル基
（例えばメトキシカルボニル基なト）、スルホニル基（
例えばメチルスルホニル基）などが挙げられる。この置
換基が２つ以上あるさきは同じでも異っていてもよい。1 of the alkylene group or phenylene group represented by F
The conversion p+= means an aryl group (e.g. phenyl group)
, nitro group, hydroxyl group, cyan group, sulfo group, alkoxy group N31. methoxy group), aryloxy group (e.g. phenoxy group), acyloxy group (e.g. acetoxy group), acylamino group (e.g. acetylamino group), sulfur, phonamide group (e.g. ehamethanesulfunamide!!!
, ), sulfamoyl & (flif methylsulfamoyl group), halokene atom (e.g. fluorine atom, chlorine atom, bromine atom, etc.), carboxy group, carbamoyl group (e.g. methylcarbamoyl group), alkoxycarbonyl group (e.g. methoxy carbonyl group), sulfonyl group (
Examples include methylsulfonyl group). When there are two or more substituents, they may be the same or different.
Ａｒ３はフェニル基を表わし、このフェニル基は置換基
を有していてもよい。置換基としては、アルキル基（例
えばメチル基、エチル基など）、アルコキシ基（例えば
メトキシ基、エトキシ基など）、アリールオキシ基（例
えはフェニルオキシ基ナト）、アルコキシカルボニル基
（例えはメトキシカルボニル基など）、アシルアミノ基
（例んばアセチルアミノ基）、カルバモイル基（例エバ
メチルカルバモイル基、エチルカルバモイル基等のアル
キルカルバモイル基、ジメチルカルバモイル基等のジア
ルキルカルバモイル基、フェニルカルバモイル基ナトの
アリールカルバモイル基）、スルホニル基、例えばメチ
ルスルホニル基等のアルキルスルホニル基、フェニルス
ルホニル基等のアリールスルホニル基、スルホンアミド
基、例えばメタンスルホンアミド基等のアルギルスルホ
ンアミド基、フェニルスルボンアミド基等のアリールス
ルホンアミド基、スルファモイル基（例エバエチルスル
ファモイル基等のアルギルスルファモイル基、ジメチル
スルファモイル基等のジアルキルスルファ七イル基）、
アルキルチオ基（例えばメチルチオ基）、アリールチオ
基（例えばフェニルチオ礒）、シアノ基、ニトロ基、ハ
ロゲン原子（例んばフッ凧原子、塩素原子、臭素原子な
ど）が孕げられ、この直換基が２１［ｉ’ｉ１以上ある
ときは互に同じＣも、また異っていてもよい０
！待ｌこ好ましい１１λ換基としては、ハロゲン原子、
アルキル基、アルコキシ基、アルコキシカルボニル基、
シアノ基が挙げらイする。Ａｒｓのオルト位の少なくと
も五つがハロゲン原子、アルキル基、アルコキシ基１こ
よつ−Ｃｔ＋ｔ 換されて、いるものが特に有用である
。Ar3 represents a phenyl group, and this phenyl group may have a substituent. Examples of substituents include alkyl groups (e.g., methyl group, ethyl group, etc.), alkoxy groups (e.g., methoxy group, ethoxy group, etc.), aryloxy groups (e.g., phenyloxy group, nato), alkoxycarbonyl groups (e.g., methoxycarbonyl group). ), acylamino group (e.g. acetylamino group), carbamoyl group (e.g. alkylcarbamoyl group such as evamethylcarbamoyl group, ethylcarbamoyl group, dialkylcarbamoyl group such as dimethylcarbamoyl group, arylcarbamoyl group such as phenylcarbamoyl group) , sulfonyl groups, such as alkylsulfonyl groups such as methylsulfonyl groups, arylsulfonyl groups such as phenylsulfonyl groups, sulfonamide groups, such as argylsulfonamide groups such as methanesulfonamide groups, and arylsulfonamides such as phenylsulfonamide groups. group, sulfamoyl group (e.g., argylsulfamoyl group such as evaethylsulfamoyl group, dialkylsulfanoyl group such as dimethylsulfamoyl group),
It contains an alkylthio group (e.g. methylthio group), an arylthio group (e.g. phenylthio group), a cyano group, a nitro group, a halogen atom (e.g. fluorine atom, chlorine atom, bromine atom, etc.), and this direct substituent group is 21 [i'iIf there are 1 or more, Cs that are the same or different may be 0! Preferred 11λ substituents include halogen atoms,
Alkyl group, alkoxy group, alkoxycarbonyl group,
Examples include cyano groups. Particularly useful are those in which at least five ortho positions of Ars are replaced by a halogen atom, an alkyl group, or one alkoxy group -Ct+t.
ｚ２ は水素原子、または酸素原子、窒素原子もしくは
イオウ原子でカップリング位に結合している離脱基を表
わす。z2 represents a hydrogen atom, or a leaving group bonded to the coupling position with an oxygen atom, nitrogen atom or sulfur atom.
ｚ２が酸素原子、室ス：原子、イオウ原子である場合に
は、これらの原子はアルキル基、アリール基、スルホニ
ル基、スルフィニル基、カルボニル基、リン酸基、チオ
カルボニル基、複素環基またはシアノ基と結合しており
、さらにｂ”ｌ ｆ？＝原子の場合は、ぞの望素原子を
含み、５Ａもしくは６員環を形成して離脱基となりつる
基をも意味するＯｋ、ｌは０または工を表わす０
芳香族−級アミン現像生薬の酸化生成物とカップリング
しない非発色性単量体（コモノマー）は、アクリル酸、
α−クロロアクリル酸、メタアクリル酸などのアクリル
アミドから誘２５さイ１．るエステル好ｔｏ＜は低級ア
ルキルエステルおよびアミド例えばアクリルアミド、メ
タアクリルアミド、ｔ−ブチルアクリルアミド、メチル
アクリレート、エチルアクリレート、ｎ−プロピルアク
リレート、ｎ−ブチルアクリレート、２−エチルへキシ
ルアクリレート、ｎ−へキシル−アクリレート、オクチ
ルメタアクリレートおよびラウリルメタアクリレート、
メチレンビスアクリルアミド、ビニルエステル例んはビ
ニルアセテート、ビニルプロピオネートおよびビニルラ
ウレート、アクリロニトリル、メタアクリロニトリル、
芳香族ビニル化合物例えばスチレンおよびその誘導体、
例えばビニルトルエン、ジビニルベンゼン、ビニルアセ
トフェノンおよびスルホスチレン、イタコン酸、シトラ
コン酸、クロトン酸、ビニリデン、クロライド、ビニル
アルキルエーテル例エバビニルエチルエーテル、マレイ
ン１賃エステル、Ｎ−ビニル−２−ピロリドン、Ｎ−ビ
ニルピリジン、２−８よひ４−ビニルピリジンなどがあ
る。When z2 is an oxygen atom, a sulfur atom, or a sulfur atom, these atoms are an alkyl group, an aryl group, a sulfonyl group, a sulfinyl group, a carbonyl group, a phosphoric acid group, a thiocarbonyl group, a heterocyclic group, or a cyano group. If it is bonded to a group, and further b"l f? = atom, it also means a group that contains each desired atom and forms a 5A or 6-membered ring and becomes a leaving group. Ok, l is 0 The non-color-forming monomer (comonomer) that does not couple with the oxidation product of the aromatic-grade amine developing crude drug is acrylic acid,
25.1. The esters preferably include lower alkyl esters and amides such as acrylamide, methacrylamide, t-butylacrylamide, methyl acrylate, ethyl acrylate, n-propyl acrylate, n-butylacrylate, 2-ethylhexyl acrylate, n-hexyl- acrylate, octyl methacrylate and lauryl methacrylate,
methylene bisacrylamide, vinyl esters such as vinyl acetate, vinyl propionate and vinyl laurate, acrylonitrile, methacrylonitrile,
Aromatic vinyl compounds such as styrene and its derivatives,
Examples include vinyltoluene, divinylbenzene, vinylacetophenone and sulfostyrene, itaconic acid, citraconic acid, crotonic acid, vinylidene, chloride, vinyl alkyl ethers such as evavinylethyl ether, maleic monoester, N-vinyl-2-pyrrolidone, N- Examples include vinylpyridine and 2-8-4-vinylpyridine.
ｌ侍にアクリル酸ニスデル、メタアクリル酸エステル、
マレイン酸エステルが好ましい０上記コモノマーは、２
種以上を一諸に使用することもできる。例えばｎ−ブチ
ルアクリレートとジビニルベンゼン、スチレント／タア
クリル酸、ｎ−ブチルアクリレートとメタアクリル酸な
どを（実用できる。l Samurai Nisdel acrylate, methacrylate ester,
Maleic acid ester is preferred 0 The above comonomer is 2
It is also possible to use more than one species at once. For example, n-butyl acrylate and divinylbenzene, styrene/taacrylic acid, n-butyl acrylate and methacrylic acid, etc. (practical).
ポリマーカラーカプラー分野では周知のごとく、前記一
般式［１］に和尚する単量体と共重合させるためのコモ
ノマーは、形成さ２”Ｌる共重合体の物理的性質および
／または化学的性質、例えば溶解度、写真コロイド組成
物の結合剤、例えばゼラチンとの相溶性、その可碗性、
熱安定性などが好影響を受けるように選択される０
次に本発明のマゼンタポリマーカップラーラテックスを
形成するのに用いらイ゛シる前記一般式〔ｌｌ〕で表わ
される単量体カプラーの具体例を下記に示すが、本発明
はこ？’Ｌらに限定さイｔない。As is well known in the field of polymer color couplers, the comonomer to be copolymerized with the monomer represented by the above general formula [1] depends on the physical and/or chemical properties of the copolymer to be formed; For example, solubility, compatibility with binders of the photographic colloid composition, such as gelatin, its potability,
Next, specific examples of the monomeric coupler represented by the general formula [ll] used to form the magenta polymer coupler latex of the present invention are selected so that thermal stability etc. are favorably affected. An example is shown below, but what about the present invention? It's not limited to 'L and others.
２−１
Ｃ１ｌＩＣＨ２ＣＮ
１
（ＪＩ２ＣＦ３
Ｍ ２−１１ ＣＨ−ＣＯＮＩＩ
７″Ｉｒ″
０ＣＨ３
ＣＩ／
Ｍ ２−２４
Ｍ ２−２５
前記一般式［ＩＡ］または［ｌＢ］で表わされるマゼン
タカプラーを本発明のハロゲン化銀写真感光材料のハロ
ゲン化銀乳剤ノーに含有せしめるには、オイルプロテク
ト分散法、ラテックス含浸法が有利に用いらイする。2-1 C1lICH2CN 1 (JI2CF3 M 2-11 CH-CONII 7″Ir″ 0CH3 CI/ M 2-24 M 2-25 The magenta coupler represented by the general formula [IA] or [lB] is halogenated according to the present invention In order to incorporate it into the silver halide emulsion of a silver photographic light-sensitive material, an oil protect dispersion method or a latex impregnation method can be advantageously used.
オイルプロテクト分散法では、例えばマゼンタカプラー
を？、７３沸点有機溶媒に、必要に応じて低沸点溶媒を
併用して浴解し、ゼラチン水溶液の如き水性バインダー
中に界面活性剤を用いて微分散せしめ、この分散体を目
的とする残水性コロイド層中に添加さイ′シる。この方
法に用いられる荷に好ましい高沸点有機溶媒としては、
ジブチルフタレート、ジオクチル７タレート、ジインデ
シル７タレート、トリフェニルホスフェート、トリクレ
ジルホスフェート、ジエチルラウリルアミド、ジブチル
ラウリルアミド、ベンジルフ、タレート、モノ７エ＝ル
ー ｐ −ｔ −フー’：ｌ−ルフェニルホスフエート
、フェノキシエタノール、ジエチレングリコールモノフ
ェニルエーテル、ジ−メトキシエチル−７タレート、ヘ
キサメチルホスホルアミドをあげることができる。また
、低沸点溶媒としては、たとえばメチルイソブチルケト
ン、β−エトキシエチルアセテート、メトキシトリグリ
コールアセテート、アセトン、メチルアセトン、メタノ
ール、エタノール、アセトニトリル、ジオキサン、ジメ
チルホルムアミド、ジメチルスルホキシド、エチルアセ
テート、ブチルアセテート、インプロピルアセテート、
ブタノール、クロロホルム、シクロヘキサン、シクロヘ
キサノール、フッ化アル−ｚ −ル等をあげることがで
きる。For example, what about magenta couplers in the oil protect dispersion method? , a 73-boiling point organic solvent is bath-dissolved in combination with a low-boiling point solvent if necessary, and finely dispersed in an aqueous binder such as an aqueous gelatin solution using a surfactant, and this dispersion is a residual aqueous colloid. Add it to the layer. Preferred high-boiling organic solvents for the cargo used in this method include:
Dibutyl phthalate, dioctyl 7-talate, diindecyl 7-thaleate, triphenyl phosphate, tricresyl phosphate, diethyl laurylamide, dibutyl lauryl amide, benzyl phthalate, mono 7-ethyl-p-t-fu':l-ruphenyl phosphate , phenoxyethanol, diethylene glycol monophenyl ether, di-methoxyethyl-7-talate, and hexamethylphosphoramide. Examples of low-boiling solvents include methyl isobutyl ketone, β-ethoxyethyl acetate, methoxytriglycol acetate, acetone, methylacetone, methanol, ethanol, acetonitrile, dioxane, dimethylformamide, dimethyl sulfoxide, ethyl acetate, butyl acetate, and propyl acetate,
Examples include butanol, chloroform, cyclohexane, cyclohexanol, al-z-ol fluoride, and the like.
また界面活性剤としては、アルキルベンゼンスルホン酸
およびアルキルベンゼンスルホン酸の如きアニオン系界
面活性剤および７才たはンルビタンセスキオレイン酸エ
ステルおよびンルビタンモノラウリン酸エステルの如き
ノニオン系界面活性剤を用いることができる。Further, as the surfactant, anionic surfactants such as alkylbenzenesulfonic acids and alkylbenzenesulfonic acids, and nonionic surfactants such as nrubitan sesquioleate and nrubitan monolaurate can be used. .
本発明のマゼンタカプラーを乳剤中に含有せしめるため
に用いられるラテックス含浸法では、カプラーを低沸点
有機浴媒に溶解し、この浴欣中にラテックスを徐々に添
加した後、低沸点溶媒を蒸発せしめカプラが含浸さイ′
１．タラデツクス溶液を得、このラテックス俗液をゼラ
チンを含む感光性乳剤に添加する方法である。このラテ
ックス含浸法に用いられる低ｄト点有機溶媒としては、
前述したオイルプロテクト分散で用いらイＬる低那点有
機溶媒が有利に用いられる。また、ラテックスとしては
アクリル酸メタアクリル酸およびそのエステル（例えは
メチルアクリレート、エチルアクリレート、ブチルメタ
アクリレート等）、アクリルアミド、メタアクリルアミ
ド、ビニルエステル（例えばビニルアセテート、ビニル
プ四゛ビオネートなど）、アクリロニトリル、スチレン
、ジビニルベンゼン、ビニルアルキルエーテル（例工ば
ビニルエチルエーテル）、マレイン酸エステル（例んハ
マレイン酸メチルエステル）、Ｎ−ビニル−２−ピロリ
ドン、Ｎ−ビニルピリジン：、２−および４−ビニルピ
リジンなどのモノマーの単独もしくは２種以上を用いて
製造さイ１．たラテックスが用いらｎる０
さらにまた、前記一般式〔Ｉｌ〕で表わされる単量たは
この単量体カプラーと、コモノマー♂の共重合体からな
るマゼンタポリマーカプラーはポリマーカプラーラテッ
クス法によって乳剤９に有利に添加さイする。この場合
、乳化重合法で作らＪしたラテックスを直゛接ゼラチン
を含む感光性乳剤に加える方法と、単量体カプラ・−の
重合で得らｆＬる対油性ポリマーカプラーをゼラチン水
沼液中にラテックスの形で分散する方法がある。どちら
の方法においても、カプラーはゼラチンを含む感光性乳
剤中の親油性微粒子中に存在している。ここでいう親油
性微粒子というのは、ゼラチン水浴液には俗解せず、別
相として存在する微粒子をいい、例んば上記オイル油滴
、ラテックスのことをいう。In the latex impregnation method used to incorporate the magenta coupler of the present invention into an emulsion, the coupler is dissolved in a low-boiling organic bath medium, the latex is gradually added to this bath, and the low-boiling solvent is evaporated. The coupler is impregnated
1. In this method, a latex solution is obtained and this latex solution is added to a photosensitive emulsion containing gelatin. The low d-point organic solvents used in this latex impregnation method include:
Low point organic solvents, such as those used in the oil protect dispersion described above, are advantageously used. In addition, latexes include acrylic acid, methacrylic acid, and its esters (e.g., methyl acrylate, ethyl acrylate, butyl methacrylate, etc.), acrylamide, methacrylamide, vinyl esters (e.g., vinyl acetate, vinyl conjugate, etc.), acrylonitrile, and styrene. , divinylbenzene, vinyl alkyl ethers (e.g. vinyl ethyl ether), maleic acid esters (e.g. hamaric acid methyl ester), N-vinyl-2-pyrrolidone, N-vinylpyridine:, 2- and 4-vinylpyridine, etc. Produced using one or more of the following monomers: 1. Furthermore, a magenta polymer coupler consisting of a monomer represented by the general formula [Il] or a copolymer of this monomer coupler and a comonomer ♂ is prepared by a polymer coupler latex method. Added to advantageously. In this case, there are two methods: adding the latex prepared by emulsion polymerization directly to a photosensitive emulsion containing gelatin, and adding the oil-resistant polymer coupler obtained by polymerizing the monomer coupler to the gelatin solution into the latex. There is a method of dispersion in the form of In both methods, the coupler is present in lipophilic microparticles in a light-sensitive emulsion containing gelatin. The term "lipophilic fine particles" as used herein refers to fine particles that exist as a separate phase in the gelatin bath solution, such as the oil droplets and latex mentioned above.
本発明に用いられるマゼンタカプラーを含有する親油性
微粒子には、メルカプタン化合物が會まれている。この
メルカプタン化合物は、この分野では公知であり、ハロ
ゲン化銀に吸着し、例んばハロゲン化銀安定化効果、化
学増感停止効果、徐白一定着時の脱銀抑制効果などがあ
る０画像の保存住そ改良する見地からはハロゲン化銀乳
剤層、ずなわち水相へのメルカプタン化合物の分配は好
ましくない。メルカプタン化合物のｌｏｇ Ｐが２未満
であると脱法不良等の問題がおこり好ましくないＱ
１ｏｇＰについてＬｔ、例えばＣｈｅｍ、 Ｒｅｖｉｅ
ｗ、 ７１ ＋５５５ （１９７１）に記載さイ１てい
るように疎水性のパラメータであり、普通は水とｎ−オ
クタツールへの化合物の分配係数Ｐとして表示さイする
。ｌｏｇ Ｐが２以上のメルカプタン化合物であイｔば
漂白一定着時の脱銀不良等の問題がおこらない。The lipophilic fine particles containing the magenta coupler used in the present invention are associated with a mercaptan compound. This mercaptan compound is well known in this field, and adsorbs onto silver halide, and has effects such as silver halide stabilization, chemical sensitization stopping effect, and desilvering suppressing effect during whitening and fixation. From the viewpoint of improving the storage quality of silver halide emulsion layers, the distribution of mercaptan compounds into the aqueous phase is not preferred. If the log P of the mercaptan compound is less than 2, problems such as poor removal may occur, which is undesirable.
71 +555 (1971), it is a parameter of hydrophobicity and is usually expressed as the partition coefficient P of a compound between water and n-octatool. If the mercaptan compound has a log P of 2 or more, problems such as poor desilvering during bleaching and fixation will not occur.
本発明に用いらイする好ましいメルカプタン化合物は、
下記一般式［１１１３で表わさイ′Ｌる。Preferred mercaptan compounds for use in the present invention are:
It is represented by the following general formula [1113].
ａｓＨｔｌｌｌｌ
式中Ｒはアルギル基、またはベンズイミダゾロ基である
。上記Ｒで表イつさイするアルキル基は、直鎖でも分岐
でもよい。例んば、メチル、エチル、ブチル、ヘキシル
、オクチ沙デシル、ヘキサデシル、ス°ククデシルなど
が挙げられる。asHtllll In the formula, R is an argyl group or a benzimidazolo group. The alkyl group represented by R above may be linear or branched. Examples include methyl, ethyl, butyl, hexyl, octidecyl, hexadecyl, and octidecyl.
またこのアルキル基は置換基を何していてもよい０置換
基としては、フェニル基（このフェニル基には置換基を
有していてもよい。）、ニトロ基、水酸基、シアノ基、
スルホ基、アルコキシ基（例えばメトキシ基、エトキシ
基など）、アリールオキシ基（例えばフェノキシ基など
）、アシルオキシ基（例えばアセトオキシ基など）、ア
シルアミノ基（例えばアセチルアミノ栽すど）、スルホ
ンアミド基（例えばメタンスルホンアミド基など）、ス
ルファモイル基（例えばメチルスルファモイル基など）
、ハロゲン原子（向えばフッ素、塩素、臭素、沃素）、
カルボキシ基、カルバモイル基（例えばメチルカルバモ
イル基なト）、アルコキシカルボニル基（例えばメトキ
シカルボニル基すど）、スルホニル基（例えばメチルス
ルホニル基など）が挙げられる。この置換ａｓが２つ以
上あるときは、互に同じでも、異なっていてもよい。Ｒ
がベンズイミダゾロ基を表わすときは、このベンズイミ
ダゾロ基のベンゼン核は置換基を有しているものであり
、アルキル基がフェニル基で置換されでいるときは、こ
のフェニル基は置換基を有していてもよい。このｉｔ
？＆基としてはアルギル基（例エバ、メチル基、エチル
基、ペンチル晶なト）、アリール基、ニトロ基、水酸基
、アミノ基、アルコキシ基（例んばメトキシ基など）、
アリールオキシ基（例えばフェノキシ基など）、アシル
オキシ懸（例えばアセトキシ基など）、アシルアミノ？
￥５（例えはアセチルアミノ基など）、スルホンアミド
）ｋ（ｙ！Ｉ、＜ばメタンスルホンアミド基など）、ス
ルファモイル基（例んばメチルスルファモイル尤なと）
、ハロゲン原子（例えば塩素、臭素など）、カルボキシ
基、カルバモイル基（例えばメチルカルバモイル基なト
）、アルコキシカルボニル塞（例えばメトキシカルボニ
ル基ナト）、スルホニル基（例えばメチルスルホニル基
なト）カ挙げられる。こイＬらの置換基が２つ以上ある
ときは、これらは互に同一であっても、また異なってい
てもよい。In addition, this alkyl group may have any substituent. Examples of substituents include phenyl group (this phenyl group may have a substituent), nitro group, hydroxyl group, cyano group,
Sulfo group, alkoxy group (e.g. methoxy group, ethoxy group etc.), aryloxy group (e.g. phenoxy group etc.), acyloxy group (e.g. acetoxy group etc.), acylamino group (e.g. acetylamino group etc.), sulfonamide group (e.g. methanesulfonamide group, etc.), sulfamoyl group (e.g. methylsulfamoyl group, etc.)
, halogen atoms (fluorine, chlorine, bromine, iodine),
Examples include a carboxy group, a carbamoyl group (eg, methylcarbamoyl group), an alkoxycarbonyl group (eg, methoxycarbonyl group), and a sulfonyl group (eg, methylsulfonyl group). When there are two or more of these substitutions, they may be the same or different. R
When represents a benzimidazolo group, the benzene nucleus of this benzimidazolo group has a substituent, and when the alkyl group is substituted with a phenyl group, this phenyl group has a substituent. may have. this it
? Examples of & groups include argyl groups (e.g., evaporation, methyl, ethyl, and pentyl groups), aryl groups, nitro groups, hydroxyl groups, amino groups, alkoxy groups (e.g., methoxy groups, etc.),
Aryloxy group (for example, phenoxy group, etc.), acyloxy group (for example, acetoxy group, etc.), acylamino?
¥5 (for example, acetylamino group, etc.), sulfonamide) k (y!I, < methanesulfonamide group, etc.), sulfamoyl group (for example, methylsulfamoyl group)
, halogen atoms (for example, chlorine, bromine, etc.), carboxy groups, carbamoyl groups (for example, methylcarbamoyl groups), alkoxycarbonyl groups (for example, methoxycarbonyl groups), and sulfonyl groups (for example, methylsulfonyl groups). When there are two or more substituents, these may be the same or different.
一般式Ｌ Ｉｌｌ ］で表イつさイ゛シ、本発明におい
て有利に用いらイ１．るメルカプタン化合物は、ｌｏｇ
Ｐが２以上であることが必要である。好ましくはｌｏ
ｇ Ｐが４乃至９の範囲である。ｌｏｇ Ｐが２未満の
メルカプタン化合物では油相への分配が少なくなると同
時に水相すなわちゼラチン水浴液相への分配が大となり
、写真性能、例えば前述した脱銀性および感度、カブリ
等が悲影響を受け好ましくない。A compound represented by the general formula L Ill ] can be advantageously used in the present invention. 1. The mercaptan compound is log
It is necessary that P be 2 or more. Preferably lo
g P is in the range of 4 to 9. Mercaptan compounds with a log P of less than 2 are less likely to partition into the oil phase and at the same time are more likely to be partitioned into the aqueous phase, that is, the gelatin water bath liquid phase. Not well received.
このｌｏｇ Ｐは、上述したように疎水性を表わすパラ
メータで、ｌｏｇＰの値の算出ζこついては、例えば森
口等のＣｈｅｍ、 Ｐｈａｒｍ、 Ｂｕｌｌ、、 ２４
、１７９９ （１９７６）にｄ８載されている。As mentioned above, this log P is a parameter representing hydrophobicity, and the calculation of the value of log P is described, for example, by Moriguchi et al. in Chem, Pharm, Bull, 24.
, 1799 (1976), d8.
ｌｏｇ Ｐはその値が大きければメルカプタン化合物が
水相に分配さ几にくく、油相に分配さイ′シる０本発明
において用いられるメルカプタン化合物はｌｏｇ Ｐの
大きいものが好ましい。If the value of log P is large, the mercaptan compound will be difficult to partition into the aqueous phase and will be difficult to partition into the oil phase.The mercaptan compound used in the present invention preferably has a large log P.
置換基を有しない直鎖もしくは分岐のアルキルメルカプ
タンはｌｏｇ Ｐの値が大きいので好ましいメルカプタ
ン化合物である。この場合アルキル２！＋９の炭素数の
８以上であるのが好ましい。Linear or branched alkyl mercaptans without substituents are preferred mercaptan compounds because they have a large log P value. In this case Alkyl 2! It is preferable that the number of carbon atoms is 8 or more with +9.
次に本発明の好ましいメルカプタン化合物について以下
に具体的に示すが、不発ｕＡばこイ’Ｌに内定されない
。Next, preferred mercaptan compounds of the present invention are specifically shown below, but are not included in the unexploited uA Bakoi'L.
（メルカプタン化合物の例示）
９１造式 ｌｏｇ Ｐ
構造式 ｌｏｇ Ｐ
Ａ−７ＣＢ１（３７ＢＩＸ３．９ ｆｉＡ−８Ｃｌ０Ｈ
２１ＳＲ４，７９
Ａ−９Ｃ１１Ｈ２５８Ｈ５，６３
Ａ−１０Ｃ１４Ｈ２，Ｓ）１ ６．４６Ａ−１１Ｃ１６
Ｈ３１ＳＨ７３０
Ａ−１２ＣＩ＠Ｈ３７ＳＨ８，１３
本発明の前記一般式（ＩＡ）、（ＩＢＩで表わさイーシ
るマゼンタカプラーおよび一般式［１１で表わさイ′ム
る単量体カプラーを含むマゼンタ−ポリマーカプラーは
、後述のハロゲン化銀乳剤中の銀１モルをこ対して５×
１０ ないしｇＸｌｏ モルの範囲で用いら孔、好まし
くはＩ Ｘ １０−２ないし８ Ｘ １０−”モルの範
囲である。(Example of mercaptan compound) 91 Structural formula log P Structural formula log P A-7CB1 (37BIX3.9 fiA-8Cl0H
21SR4,79 A-9C11H258H5,63 A-10C14H2,S)1 6.46A-11C16
H31SH730 A-12CI@H37SH8,13 The magenta-polymer coupler of the present invention, which includes a magenta coupler represented by general formula (IA) (IBI) and a monomer coupler represented by general formula [11], is described below. 1 mole of silver in a silver halide emulsion of 5×
The range of pores used is from 10 to gXlo moles, preferably from Ix10-2 to 8x10" moles.
また親油性微粒子中の前記マゼンタカプラーの占める割
合は０．０５〜ＡｓＮ、貧パーセントで、好マしくは０
．１〜６重量パーセントである。Further, the ratio of the magenta coupler in the lipophilic fine particles is 0.05 to AsN, a poor percentage, preferably 0.
．． 1 to 6 weight percent.
さらにまた、この酸油性微粒子中のメルカプタン化合物
の占める割合は、マセンタカプツー１菫置部に対して０
．０１乃至３０ｉｉ部、好ましくは０．０３乃至ｉｏ重
量部である。Furthermore, the ratio of the mercaptan compound in the acidic and oily fine particles is 0 to 1 part of masenta captu.
．． 01 to 30ii parts, preferably 0.03 to io parts by weight.
本発明ｔこ従って得らｎたマゼンタカプラーとメルカプ
タン化合物を宮む親油性微粒子は、通常、緑感性ハロゲ
ン化銀乳剤に添加さイする。この場合、前記親油性微粒
子と共に、必要に応じて安定剤、硬膜剤、その他各桃の
写真用添加剤を添加して感光性乳剤に調製さイ”Ｌる。The lipophilic fine particles containing the magenta coupler and mercaptan compound obtained according to the present invention are usually added to a green-sensitive silver halide emulsion. In this case, a photosensitive emulsion is prepared by adding stabilizers, hardeners, and other photographic additives, as required, along with the lipophilic fine particles.
本発明により調製さイｔた上記の緑感性ノーロゲン化銀
乳剤は感光層として支持体上に塗布される。The above-mentioned green-sensitive silver norogenide emulsion prepared according to the present invention is coated on a support as a light-sensitive layer.
本発明に係るハロゲン化銀写真感光材料のハロゲン化銀
乳剤層ζこ用いるハロゲン化銀としては、塩化銀、臭化
・銀、沃化銀、塩臭化銀、沃臭化銀、塩沃臭化銀等の通
常のハロゲン化銀写真乳剤に使用さイする任意のものが
包含される。The silver halide emulsion layer of the silver halide photographic light-sensitive material according to the present invention ζThe silver halide used here includes silver chloride, silver bromide, silver iodide, silver chlorobromide, silver iodobromide, and silver iodobromide. Any of those used in conventional silver halide photographic emulsions such as silver oxide are included.
これらのハロゲン化銀粒子は、粗粒のものでも、微粒の
ものでもよく、粒径の分布は狭くても広くてもよい。ま
た、こ几らのノ１０グン化銀粒子の結晶は、正常晶でも
双晶でもよく、［１００１面と、（Ａｌｌ）面の比率は
任意のものが１史用できる。更にこれらのハロゲン化銀
粒子の結晶構造は、内部から外部まで均一なものであっ
ても、内部と外部が異質の層状構造をしたものであって
もよい０また、これらのハロゲン化銀は陽像を主として
表面に形成する型のものでも、粒子内部ｌこ形成する型
のものでもよい０これらのハロゲン化銀粒子は・、当業
界において慣用さイｔている公知の方法によって刺製す
ることができる。そしてこのノＡロゲン化銀は一般にゼ
ラチン中に分散さイ１．るが、ゼラチンの他例えばポリ
ビニルアルコール等のポリマー類もゼラチンに代えある
いはゼラチンと混合して用いらｎる。このハロゲン化銀
が適当なバインダー中に分散されたハロゲン化銀乳剤は
化学的に増感せしめ得る。これらは従来から行なわイし
ている任意の方法で行なわれる。すなわち活性ゼラチン
、水溶性金塩、水浴性白金塩、水浴性パラジウム塩、水
溶性ロジウム塩、水浴性イリジウム塩等の負金属増感剤
：硫黄増感剤：セレン増感剤：ポリアミン、塩化第１錫
等の還元増感剤等の化学増感剤等により単独ｌこあるい
は併用して化学増感さＫｌ、ることができる。史にこの
ハロゲン化銀は所望の波長域に光学的に増感することが
でき、例えばゼロメチン色素、モノメチン色素、ジメチ
ン色素、トリメチン色素等のシアニン色素あるいはメロ
シアニン色素等の光学増感剤を単独あるいは併用して（
例えば超色増Ｉ（＆）光学的に増感することができるま
た本発明に係るハロゲン化銀写真感光材料には公知の２
当−Ｊ、ｉ、４当量カプラーを１史用できる。These silver halide grains may be coarse or fine, and the grain size distribution may be narrow or wide. Furthermore, the crystals of the No. 10 silver grains of Konori et al. may be normal crystals or twin crystals, and any ratio of the [1001 plane to the (All) plane can be used. Furthermore, the crystal structure of these silver halide grains may be uniform from the inside to the outside, or may have a layered structure with different inside and outside layers. These silver halide grains may be of a type in which an image is mainly formed on the surface or a type in which an image is formed inside the grain. I can do it. This silver halide is generally dispersed in gelatin.1. However, in addition to gelatin, polymers such as polyvinyl alcohol can also be used instead of gelatin or mixed with gelatin. Silver halide emulsions in which the silver halide is dispersed in a suitable binder can be chemically sensitized. These can be done by any conventional method. Namely, activated gelatin, water-soluble gold salts, water-based platinum salts, water-based palladium salts, water-based rhodium salts, water-based iridium salts, and other negative metal sensitizers: sulfur sensitizers: selenium sensitizers: polyamines, dichloride sensitizers, etc. Chemical sensitization can be carried out using a chemical sensitizer such as a reduction sensitizer such as tin or the like, either alone or in combination. Historically, this silver halide can be optically sensitized to a desired wavelength range, for example by using an optical sensitizer such as a cyanine dye such as a zeromethine dye, a monomethine dye, a dimethine dye, a trimethine dye, or a merocyanine dye alone or by using an optical sensitizer such as a merocyanine dye. Used together (
For example, the silver halide photographic light-sensitive material according to the present invention, which can be optically sensitized with superchromatic I(&),
The -J, i, 4-equivalent coupler can be used in one history.
イエローカブシーとしては開鎖ケトメチレン系カプラー
を用いることができる。As the yellow turnip, an open chain ketomethylene coupler can be used.
また更に併用し得るマスキングカプラーとしてのカラー
ド・マゼンタカプラーとしては一般的にはカラーレス・
マゼンタカプラーの活性点にアリールアゾ基を置換した
化合物が用いられ、例えば米国特許第２，８０１，１７
１号、同第２，９８３．６０８号、同第３，００５，７
１２号、同第３，６８４．５１４号、英国特許第９３７
，６２１号、特開昭４９−１２３６２５号、同４９−１
３１４４８号などに記Ｉ＠すれている化合物が挙げられ
る。In addition, colorless magenta couplers are generally used as masking couplers that can be used in combination with colorless magenta couplers.
A compound in which an arylazo group is substituted at the active site of a magenta coupler is used, for example, US Pat. No. 2,801,17
No. 1, No. 2,983.608, No. 3,005,7
No. 12, No. 3,684.514, British Patent No. 937
, No. 621, JP-A-49-123625, JP-A No. 49-1
Examples include compounds described in No. 31448 and the like.
更に米国特許第３，４１９，３９１号に記載さイ１．で
いるような発色現像主薬の酸化生成物との反応で色素が
処理浴中に流出していくタイプのカラード・マゼンタカ
プラーも用いることができる。更にシアンカプラーとし
ては、一般にフェノールまたはナフトール誘導体が用い
られる。その具体例は、米国特許第２，４２３．７３０
号、＋ＤＪ第２，４７４，２９３号、同第２．８０１．
１７１号、同第２，８９５．８２６号、同第３．４７６
．５６３号、同第３ 、 ’１３７ 、３１６号、１６
ｊ第３．７５８．３０８号、同第３．８３９．０４４号
、同第３゜９９８．６４２号、特開昭４７−３７４２５
号、同５０−１０１３５号、同５０−２５２２８号、
同５０−１１２０３８号、四５０−１１７４２２号、同
５０−１３０４４１号、同５１−２１８２８号、同５２
−１８３１５号、同５３−５２４２３号、同５３−１０
５２２６号、同５３−１０９６３０号などに記載されて
いる。Further described in U.S. Pat. No. 3,419,391: 1. Colored magenta couplers of the type in which the dye is leached into the processing bath by reaction with the oxidation products of the color developing agent can also be used. Furthermore, as cyan couplers, phenol or naphthol derivatives are generally used. A specific example is U.S. Patent No. 2,423.730
+DJ No. 2,474,293, +DJ No. 2.801.
No. 171, No. 2,895.826, No. 3.476
．． No. 563, No. 3, '137, No. 316, 16
j No. 3.758.308, No. 3.839.044, No. 3998.642, JP-A-47-37425
No. 50-10135, No. 50-25228,
No. 50-112038, No. 450-117422, No. 50-130441, No. 51-21828, No. 52
-18315, 53-52423, 53-10
No. 5226, No. 53-109630, etc.
マスキング・カプラーとしてのカラード・シアンカプラ
ーとしてはカラーレス・シアンカプラーの活性点にアリ
ールアゾ基を置換した化合物が用いらｎ２例えば米国特
許第２，５２１．９０８号、同第３．０３４，８９２号
、英国特許第１，２５５，１１１号、特開昭４８−２２
０２８号などに記載さイｔている化合物が挙げられる。As a colored cyan coupler as a masking coupler, a compound in which an arylazo group is substituted at the active site of a colorless cyan coupler is used. For example, U.S. Pat. No. 2,521.908, U.S. Pat. British Patent No. 1,255,111, Japanese Unexamined Patent Publication No. 48-22
Examples include compounds described in No. 028 and the like.
更に米Ｉ］ｉｌ特許ｉｉｓ＊４ｒ６．５６３号、特開昭
５０−１０１３５号、同５０−１２３３４１号などに
記載されているような発色現像生薬の酸化生成物との反
応で色素が処理浴中に流出していくタイプのカラード・
シアンカプラーも用いることができる。In addition, dyes are produced in the processing bath by reaction with oxidation products of color developing crude drugs as described in US I]IL Patent IIS*4R6.563, JP-A No. 50-10135, JP-A No. 50-123341, etc. The type of colored that flows into
Cyan couplers can also be used.
また写Ａ特性を向上するために、所謂コンビ−ティング
・カプラーと呼ばれる無色色素を形成するカプラーを含
むこともできる。Furthermore, in order to improve the photo-A characteristics, a so-called combining coupler, which forms a colorless dye, can also be included.
また本）Ｊら明に係るハロゲン化銀写Ｘ感元材料は、感
光層及び／または他の構成層（例凡ば中間層、下引層、
フィルター層、保岐層、受像層等）に目的に応じてこの
他の種々の写真用添加剤を含むことができる。In addition, the silver halide photographic X-sensitive source material according to this book) J et al.
Various other photographic additives may be included in the filter layer, hoki layer, image-receiving layer, etc. depending on the purpose.
例んばアザインデン類、トリアゾール類、テトラゾール
知イミダゾリウム塩、テトラゾリウム塩ポリヒドロキシ
化合物等の安定剤やカプリ防止剤；アルデヒド系、アジ
リジン系、イノオキサゾール系、ビニルスルホン系、ア
クリロイル系、アルホシイミト系、マレイミド系、メタ
ンスルホンｔＷｌエステル系、トリアジン系等の硬膜剤
；箱８属の金Ｍ（たとえばロジウム、ルデニウム）ある
いはカドミニウム、タリウム等の階調調整剤；ベンジル
アルコール、ポリオキシエチレン系化合物等の現像促進
剤；クロマン系、クラマン系、ビスフェノール系、亜リ
ン酸エステル系の画像安定剤；ワックス、＾級脂肪酸の
グリセライド、重数脂肪酸の高級アルコールエステル等
の■滑剤等がある。For example, stabilizers and anti-capri agents such as azaindenes, triazoles, tetrazole-known imidazolium salts, tetrazolium salt polyhydroxy compounds; aldehyde-based, aziridine-based, inoxazole-based, vinylsulfone-based, acryloyl-based, alphoshiimite-based, maleimide-based Hardeners such as methane sulfone tWl ester, triazine, etc.; gradation adjusters such as Box 8 gold M (e.g. rhodium, rhudenium) or cadmium, thallium; developing agents such as benzyl alcohol, polyoxyethylene compounds, etc. Accelerators: Chroman-based, Claman-based, bisphenol-based, and phosphite-based image stabilizers; lubricants such as waxes, glycerides of tertiary fatty acids, and higher alcohol esters of heavy fatty acids;
又界面活性剤として塗布助剤、乳化剤、処理液等ζこ対
する浸透性の改良剤、消泡剤あるいは感光材料の種々の
物理的性質のコントロールのための素材として、アニオ
ン型、カチオン型、非イオン型あるいは両性の各種のも
のが使用できる。モルダントとしてはＮ−グアニルヒド
ラゾン系化合物、４級オニウム塩化合物等が有効である
。帯電防止剤トしてはジアセチルセルローズ、スチレン
パーフルオロアルキルリジウムマレエート共重合体、ス
チレン−無水マレイン識共凪合体とｐ−アミンベンゼン
スルホン酸との反応物のアルカリ塩等が有効である。色
濁り防止剤としてはビニルビＯリドン単量体を含むポリ
マー、ビニルイミダゾール単量体を含むポリマー等を埜
げることができる。Also, as surfactants, coating aids, emulsifiers, permeability improvers for processing liquids, antifoaming agents, and materials for controlling various physical properties of photosensitive materials, such as anionic, cationic, and non-ionic. Various ionic or amphoteric types can be used. As the mordant, N-guanylhydrazone compounds, quaternary onium salt compounds, etc. are effective. Effective antistatic agents include diacetyl cellulose, styrene perfluoroalkyl rhidium maleate copolymers, and alkali salts of reaction products of styrene-maleic anhydride copolymer and p-aminebenzenesulfonic acid. As the color turbidity inhibitor, polymers containing vinyl bi-Olidone monomers, polymers containing vinyl imidazole monomers, etc. can be used.
マット剤としてはポリメタアクリル酸メチル、ポリスチ
レンおよびアルカリ可溶性ポリマーなどが挙げらｉする
。またさらにコロイド状酸化珪素の使用も可ｈヒである
。またｊ換物性を向上するために添加するラテックスと
してはアクリル酸エステル、ビニルエステル等と他のエ
チレン基を持つ拳蓋体との共、屯介体８挙げることがで
きる。ゼラチン可塑剤としてはグリセリン、グリコール
系化合物等を桔げることかでき、増粘剤としてはスチレ
ン−マレイン酸ソーダ共本合体、アルキルビニルエーテ
ル−マレイン酸共重合体等が挙げられる。Examples of matting agents include polymethyl methacrylate, polystyrene, and alkali-soluble polymers. It is also possible to use colloidal silicon oxide. Examples of the latex added to improve the conversion properties include acrylic esters, vinyl esters, and other ethylene group-containing latexes. Examples of the gelatin plasticizer include glycerin and glycol compounds, and examples of the thickener include styrene-sodium maleate copolymer and alkyl vinyl ether-maleic acid copolymer.
本発明に係るハロゲン化銀写真感光材料は、心安に応じ
て前記の妬き独々の写真用添加剤を含有せしめたハロゲ
ン比銀乳剤層８よぴその他の構成層を支持体上に塗設す
ることによって製造される０有利に用いら７する支持体
としては、たとえば、バライタ紙、ポリエチレン被徨紙
、ポリプロピレン合成紙、ガラス紙、セルロースアセテ
ート、セルロースナイトレート、ポリビニルアセタール
、ポリプロピレン、たとえばポリエナレンテレフタレー
ト等のポリエステルフィルム、ポリスチレン等がありこ
イｔらの支持体はそれぞれのハロゲン化銀写真感光材料
の使用目的に応じて適宜選択される０
こわらの支持体は必要に応じて下引加工が施される０
本発明のハロゲン化銀写ＡＭ＆ブＣ材料は露光後進常用
いらＪｌ、る周知の方法により現像処理することができ
る。In the silver halide photographic material according to the present invention, the silver halide emulsion layer 8 and other constituent layers containing the above-mentioned proprietary photographic additives are coated on a support. Advantageously used supports include, for example, baryta paper, polyethylene-covered paper, polypropylene synthetic paper, glass paper, cellulose acetate, cellulose nitrate, polyvinyl acetal, polypropylene, such as polyenalene terephthalate. There are polyester films, polystyrene, etc. These supports are appropriately selected depending on the intended use of each silver halide photographic light-sensitive material.The stiff supports can be subbed as necessary. After exposure, the silver halide photographic AM&B C material of the present invention can be developed by a commonly used method.
たとえば通常用いら４する発色現像法で発色現像するこ
とができる。反転法ではまず黒白ネガ現像液で現像し、
次いで白色露光を与えるか、あるいはカプリ剤を含有す
る浴で処理し、さらに発色現像主薬を含むアルカリ現像
液で発色現像する。処理方法については特に制限はなく
あらゆる処理方法が適用できるが、たとえばその代表的
なものとしては、発色現像後、（県白定着処理を行ない
必要に応じさらに水洗、安定処理を行なう方式、あるい
は発色現像後、赫白と定着を分離して行ない必要に応じ
さらに水洗、安定処理を行なう方式によるものをあげる
ことができる。また過酸化水素コバルト錯塩の如きアン
ブリファイヤー剤を用いて低ハロゲン化銀感光材料を処
理することも知られており、こイＬらの方式を用いて処
理することもできる。またこわらの処理は迅速に行なう
ため高温で行なわれる場合もあり、室温またはｑ！ｆ殊
な場仕にはそイｔＰＪ、下で行なわ？’Ｌろこともある
。高温迅速処理を行なう際には前硬膜処理も行なうこと
ができる。また用いらイＬる処理剤の桓ジ「１に応じて
、各極の中和浴など補助浴が必要になる場合もあり必要
に応じ適宜これらの補助浴を用いることができるＯ
本発明に係るハロゲン化銀写真感光材料を発色現１８！
するのに用いらｒＬるとくｌこ有用な発色現像主薬は第
１級のフェニレンジアミン類およびその誘導体でたとん
ば次の如きものをその代表例とじてあげることができる
。For example, color development can be carried out by a commonly used color development method. In the reversal method, the image is first developed with a black and white negative developer,
It is then exposed to white light or treated with a bath containing a capri agent and further color developed with an alkaline developer containing a color developing agent. There are no particular restrictions on the processing method, and any processing method can be applied; for example, typical methods include a method in which after color development, (prefecture white fixing treatment is performed, followed by further washing with water and stabilization treatment as necessary), or color development. After development, brightening and fixing are carried out separately, and if necessary, washing with water and stabilizing treatment are carried out.Also, an amplifying agent such as hydrogen peroxide and cobalt complex salt is used to achieve low silver halide sensitization. It is also known to treat materials and can be done using the method of Koi L et al. Processing of stiff materials may also be carried out at high temperatures for rapid processing, and may be carried out at room temperature or at In other cases, it may be necessary to carry out the process under the PJ.Pre-hardening treatment can also be performed when performing high temperature rapid treatment. 1, auxiliary baths such as neutralization baths for each pole may be required, and these auxiliary baths may be used as necessary.
Typical examples of useful color developing agents used for this purpose include primary phenylene diamines and derivatives thereof.
４−アミノ−Ｎ、Ｎ−ジエチルアニリン、３−メチル−
４−アミノ−Ｎ、Ｎ−ジメチルアニリン、４−アミノ−
Ｎ−エチル−Ｎ−β−ヒドロキシエチルアニリン、３−
メチル−４−アミノ−Ｎ−エチル−Ｎ−β−ヒドロキシ
エチルアニリン、３−メチル−４−アミノ−Ｎ−エチル
−Ｎ−β−メタンスルホンアミドエチルアニリン、３−
メチル−４−アミノ−Ｎ−エチル−Ｎ−β−メトキシエ
チルアニリン、３−β−メタンスルホンアミドエチル４
−アミノ−Ｎ、Ｎ−ジエチルアニリン、３−メトキシ−
４−アミノ−Ｎ−エチル−Ｎ−β−ヒドロキシエチルア
ニリン、３−メトキシ−４−アミノ−Ｎ−エチル−Ｎ−
β−メトキシエチルアニリン、３−アセトアミド−４−
アミノ−Ｎ、Ｎ−ジエチルアニリン、４−アミノ−Ｎ、
Ｎ−ジメチルアニリン、Ｎ−エチル−Ｎ−β−〔β−（
β−メトキシエトキシ）エトキシ〕エチルー３−メチル
−４−アミノアニリン、Ｎ−エチル−Ｎ−β（β−メト
キシエトキシ）エチル−３−メチル−４−アミノアニリ
ンやこてしらの塩、例えば健酸塩、塩酸塩、亜鯰酸塩、
ｐ−トルエンスルホン酸塩などである。4-Amino-N, N-diethylaniline, 3-methyl-
4-amino-N, N-dimethylaniline, 4-amino-
N-ethyl-N-β-hydroxyethylaniline, 3-
Methyl-4-amino-N-ethyl-N-β-hydroxyethylaniline, 3-methyl-4-amino-N-ethyl-N-β-methanesulfonamidoethylaniline, 3-
Methyl-4-amino-N-ethyl-N-β-methoxyethylaniline, 3-β-methanesulfonamidoethyl 4
-Amino-N, N-diethylaniline, 3-methoxy-
4-amino-N-ethyl-N-β-hydroxyethylaniline, 3-methoxy-4-amino-N-ethyl-N-
β-methoxyethylaniline, 3-acetamido-4-
Amino-N, N-diethylaniline, 4-amino-N,
N-dimethylaniline, N-ethyl-N-β-[β-(
β-Methoxyethoxy)ethoxy]ethyl-3-methyl-4-aminoaniline, N-ethyl-N-β(β-methoxyethoxy)ethyl-3-methyl-4-aminoaniline and salts of Koteshira, such as salt salts , hydrochloride, catfish salt,
p-toluenesulfonate and the like.
（ｏ） 発明の具体的実施例
次に実施例をあげて本発明を例址するが本発明がこれに
より限定さイーシるものではない０実施例１
例示カプラー（ｈｉ−６） ｌ ｇＳｆｉｌに示される
本発明の谷柚のメルカプタン化合物をそイｔぞれ、ジブ
チルフタレート０．５ ｒｎｔおよび酢酸エチル３〇−
との混合物をスチームバス上で加熱浴解し、こイしをゼ
ラチンのｌＯチ水溶液１０ｇに加えドデシルベンゼンス
ルポン酸ツートリウム０．５’ｇを含ム水１ｄ液をη≦
加してホモジナイザーにより激しく撹拌しマゼンタカプ
ラーの乳化分散物を得た。次に上記乳化分散物を塩臭化
銭（塩鶏銀５０モルチ、臭化銀５０モル％）４．７Ｘｌ
Ｏモルとゼラチン９ｇを言む緑感性ノ・ロゲン化銀乳剤
１００ ｇと混合して、硬１漠剤として２−ヒドロキシ
−４，６−ジクロロ−８−）リアジンのナトリウム塩４
チ水溶液３ ｍ／を添加し、更薔こＰＨを６．３に調節
した。得らイｔた混合液を写真用ポリエチレンラミネー
ト紙上Ｅこ、乾燥膜厚２μになるように塗布し、表１に
示す試料ｔ、２，３．４および５を作成した０このうち
、試料ｌは、本発明のメルカプタン化合物がマゼンタカ
プラーを含有する親油性微粒子中に添加されていない本
発明外の比較試料であり、試料２はメルカプタン化合物
のｌｏｇ Ｐが２以下の本発明外の比較試料である。(o) Specific Examples of the Invention The present invention will now be illustrated by examples, but the present invention is not limited thereto.Example 1 Exemplary coupler (hi-6) shown in l gSfil Each of the taniyu mercaptan compounds of the present invention, dibutyl phthalate 0.5 rnt and ethyl acetate 30-
The mixture was dissolved in a heating bath on a steam bath, and the strained mixture was added to 10 g of a 1O2 aqueous solution of gelatin, and 1 d of aqueous solution containing 0.5 g of dodecylbenzenesulfonic acid was added to η≦
In addition, the mixture was vigorously stirred using a homogenizer to obtain an emulsified dispersion of magenta coupler. Next, add 4.7Xl of the above emulsified dispersion (50 mol of salted chicken silver, 50 mol% of silver bromide) to
The sodium salt of 2-hydroxy-4,6-dichloro-8-) riazine as a hardening agent was mixed with 100 g of a green-sensitive silver halide emulsion containing Omol and 9 g of gelatin.
3 m/ml of an aqueous solution of chloride was added to adjust the pH of the radish to 6.3. The obtained mixed solution was applied on photographic polyethylene laminate paper to a dry film thickness of 2μ to prepare samples t, 2, 3.4 and 5 shown in Table 1. Sample 2 is a comparative sample other than the present invention in which the mercaptan compound of the present invention is not added to the lipophilic fine particles containing magenta coupler, and Sample 2 is a comparative sample other than the present invention in which the log P of the mercaptan compound is 2 or less. be.
上記により得られた各試料１〜５について、緑色光によ
るウェッジ露光を行なった後、下記の処理方法に従って
発色３Ａ像処理した０
（処理工程） （温度） （時 間）
発色現像 ３８ ’０ ３分３０秒
漂白定着 １分３０秒
水 洗 ２分
（発色現像液組成）
Ｎ−エチル−Ｎ−β−メタンスルホンアミドエチル−３
−メチル−４−アミノアニリン値酸塩 ４．０ｇ
ヒドロキシルアミン ２・０ｇ
炭酸カリウム ２５．０ｇ
塩ｒｌＺナトリウム ０．１ｇ
臭化ナトリウム ゛０．２ｇ
無水亜似にナトリウム ２．０ｇ
ベンジルアルコール １０．０ｍ
ポリエチレングリコール（平均重合度４００）３、〇−
水を加７ＬＣ１ｌ！とじ、水酸化ナトリウムを用いてＰ
Ｈ１０，０にｒＡ＋ａする。Each of the samples 1 to 5 obtained above was subjected to wedge exposure with green light, and then subjected to color 3A image processing according to the processing method described below. minutes 30 seconds bleach fixing 1 minute 30 seconds water washing 2 minutes (color developer composition) N-ethyl-N-β-methanesulfonamidoethyl-3
-Methyl-4-aminoaniline acid salt 4.0g Hydroxylamine 2.0g Potassium carbonate 25.0g Sodium salt 0.1g Sodium bromide 0.2g Anhydrous sodium chloride 2.0g Benzyl alcohol 10.0m Polyethylene Glycol (average degree of polymerization 400) 3, 〇- Add water 7LC1l! Bind and P with sodium hydroxide.
Add rA+a to H10,0.
（細白定沼故ｍｂｉ、）
エチレンジアミンテトラ酢酸・鉄ナトリウム塩６０．０
ｇ
チオ眺鹸アンモニウム １００．０ｇ
４て亜イＶ比酸す ト リ ウ ム １０．０ｇメタ重
亜硫酸ナトリウム ３．０ｇ
水を加入でｌｌ！とじ、アンモニア水を用いてＰＨ６，
６に調整する。(Hosohaku Sadanuma late mbi,) Ethylenediaminetetraacetic acid iron sodium salt 60.0
g Thiochloride ammonium 100.0g 4% sulfite V specific acid thorium 10.0g Sodium metabisulfite 3.0g Add water! Binding, pH 6 using ammonia water,
Adjust to 6.
次に現像処理済みの上記谷試料１〜５のそれぞれについ
て６０゛０で７５％ＲＨ（相対湿度）下に１４日間暗所
に放置した後、青色光により非画像部のスティンを測定
した。その結果を第１表に示す。Next, each of the developed valley samples 1 to 5 was left in the dark at 60°C and 75% RH (relative humidity) for 14 days, and then the stain in the non-image area was measured using blue light. The results are shown in Table 1.
第 １ 表
第１表から明らかなように、本発明によるメルカプタン
化合物を含有する試料３ 、４ｊ６よび５は、本発明外
の試料ｌおよび２と比較して著しく湿熱スティンが改良
されていることがイつかる。またメルカプタン化合物の
ｌｏｇＰが２以下である化合物ａを含■する試料２では
、湿熱スティンが若干改善さ４１． ’ｒはいるが、脱
銀性が劣っていることが判る。また本発明のメルカプタ
ン化合物を含有する試料３．４８よひ５の中では、ｌｏ
ｇ Ｐの値が大版いものはど湿熱スティンが改善されて
いること１１Ｓ旬る。Table 1 As is clear from Table 1, Samples 3, 4j6 and 5 containing the mercaptan compound according to the present invention have significantly improved moist heat staining compared to Samples 1 and 2 outside the present invention. I'm going to use it. In addition, in sample 2 containing compound a whose log P of the mercaptan compound is 2 or less, the moist heat stain was slightly improved by 41. 'r is present, but it can be seen that the desilvering properties are inferior. Moreover, among samples 3.48 and 5 containing the mercaptan compounds of the present invention, lo
If the value of gP is large, the humidity and heat stain will be improved in 11S.
実施例２
特開昭５７−２０４０３８号公報記絨の製造物心従って
１−フェニル−３−メタアクリルアミド−２−ピラゾリ
ン−５−オン（Ｍ ２−７の単重体力プラー）とｎ−ブ
チルアクリレートのコポリマーラテックスから７．「る
マゼンタポリマーカプラーラテックスを製造した。Example 2 According to the manufacturing method described in JP-A-57-204038, 1-phenyl-3-methacrylamido-2-pyrazolin-5-one (M2-7 single weight puller) and n-butyl acrylate were prepared. 7. From copolymer latex. We have produced a magenta polymer coupler latex.
このマゼンタポリマーカプラーラテックスの重合体磯此
は２７．６ ’％であり、笥た蟹素分析によりコポリマ
ー中の１−フェニル−３−メタアクリルアミド−２−ピ
ラゾリン−５−オン（Ｍ ２−７ ）の４″Ｌ延体カプ
ラー）の會有厩は１８％であった。The polymer content of this magenta polymer coupler latex was 27.6'%, and 1-phenyl-3-methacrylamido-2-pyrazolin-5-one (M2-7) in the copolymer was determined by molecular analysis. The total capacity of the 4″L extended coupler was 18%.
上。己のマゼンタポリマーカプラーラテックス２０ｃｃ
に５ｃｃの塩酸を加えた後、こｎをろ遇、乾燥し、同形
成分５．５ｇを得た。この固形成分５．５ｇをメタノー
ル２０ｃｃに溶解し、本発明のオクタデシルメルカプタ
ン（Ａ−１２、ｌｏｇＰ＝８．１３）０．１ｇを添加し
、撹拌後メタノールを蒸発した。Up. My magenta polymer coupler latex 20cc
After adding 5 cc of hydrochloric acid to the solution, the mixture was filtered and dried to obtain 5.5 g of the same component. 5.5 g of this solid component was dissolved in 20 cc of methanol, 0.1 g of octadecyl mercaptan (A-12, logP=8.13) of the present invention was added, and after stirring, methanol was evaporated.
上記ポリマーラテックス２０ｃｃになるように丹分散し
てオクタデシルメルカプタンを含有Ｊ−るマゼンタポリ
マーカプラーを得たにｒシララテックス浴液ＬＸとする
。）。The above polymer latex was dispersed in 20 cc to obtain a magenta polymer coupler containing octadecyl mercaptan, which is referred to as a sila latex bath liquid LX. ).
次に上記ポリマーラテックス溶液（ＬＸ）を、塩化銀５
０モルチと臭化銀５０モルチとからなる塩臭化銀４．７
ＸＩＯモルとゼラチン９ｇとヲ含む緑感性ハロゲン化銀
乳剤１００ｇと混会して、更ｌこ硬Ｊ摸剤おして２−ヒ
ドロキシ−４，６−ジクロロ−ｓ−トリアジンのナトリ
ウム塩４％水田液３−を添加し、更にＰＨを６．３に調
節した。得らｎた混合液を写真用ポリエチレンラミネー
ト紙上に、乾燥時の膜厚が２μになるように塗布し試料
を作成し、こｎを試料６とした。Next, the above polymer latex solution (LX) was mixed with silver chloride 5
Silver chlorobromide 4.7 consisting of 0 molti and 50 molti silver bromide
The sodium salt of 2-hydroxy-4,6-dichloro-s-triazine was mixed with 100 g of a green-sensitive silver halide emulsion containing 9 g of gelatin and 100 g of a green-sensitive silver halide emulsion containing 10 moles of gelatin and 4% paddy solution 3 of the sodium salt of 2-hydroxy-4,6-dichloro-s-triazine. - was added and the pH was further adjusted to 6.3. A sample was prepared by applying the obtained mixed solution onto photographic polyethylene laminate paper so that the dry film thickness was 2 μm, and this sample was designated as Sample 6.
次に比較用として、上記ラテックス浴液（ＬＸ）の代り
Ｇこ本発明ベカオクタデシルメルカブタン（Ａ−１２）
４除いた以外は前記方法と同じ方法で試料を作成し、こ
イ′シを試料７とした。Next, for comparison, G instead of the latex bath liquid (LX) was prepared using becaoctadecylmercabutane (A-12) of the present invention.
A sample was prepared in the same manner as described above except that No. 4 was removed, and this sample was designated as Sample No. 7.
上記ζこより得らＩＥ、た試料６ ’１６よび７１こつ
いて実ｈｉｉ例と＋ＩＸ＋じように緑色光にウェッジ露
光後、発色現像処理し、イ）チらイ″ＬＬ試料ｌこつい
て実施例工と同じ信性にてステーｆンの発生を做祭し第
２表の結果を得た。Samples 6'16 and 71 obtained from the above were subjected to color development after wedge exposure to green light, as in the actual example and +IX+. We assumed the occurrence of stage f with the same reliability as that of the previous example, and obtained the results shown in Table 2.
ｌ：ｉ４ ２ 表
非ｌ１ＩＩｉ像部の
試料 メルカグタン化合物 湿熱ユヶイ、ノ偵度６（本
発明） Ａ−１２０，１９
７（比軸） −０，２７
４番２表から明らかなように、マゼンタポリマーカプラ
ーにメルカブタ／化仕物を含有する本発明の試料では、
比較試料に比べて湿熱スデインが著じるしく改良さイｔ
ていることがわかる。l:i4 2 Sample in the non-l1IIi image area of the table Mercagtan compound Moist heat resistance, No. 6 (invention) A-120,19 7 (specific axis) -0,27 As is clear from Table 4 and 2, magenta polymer In the sample of the present invention containing merkabuta/chemical compound in the coupler,
Humid heat suden was significantly improved compared to the comparative sample.
It can be seen that
出 願 人 小西六写真工莱株式会社Applicant: Konishiroku Photography Co., Ltd.
Claims (1)
が含有さイｔている親油性微粒子を分散したハロゲン化
銀乳剤層を有するハロゲン化銀感光材料において、前６
己親油性微粒子中にメルカプタン化合物が含有されてい
ることを特徴とするハロゲン化銀写真感光材料。 （２） 前記メルカプタン化合物は２以上のｌｏｇ ｐ
（但シ、ｐは水とｎ−オクタツールへの分配係数を六イ
つす。）を有することを特徴とする特許請求の範囲第（
４）項記載のハロゲン化銀写真感光材料。 （３） 前記メルカプタン化合物が下記一般式［１３で
表わさイすることを特徴とする特許請求の範囲第Ｔｌ１
項又は第（２）項記載のノ・ロゲン化銀写真感光材料一
般式（ｌ］ ＳＨ （式中、Ｒはアルキル基又はベンズイミダゾロ基を表わ
す。） （４）、前記一般式［Ｉ］において、Ｒがアルギル基で
あることを特徴とする特許請求の範囲第（３）ＪＪＫ記
載のハロゲン化銀写真感光材料。[Scope of Claims] (U) A silver halide photosensitive material having a silver halide emulsion layer in which lipophilic fine particles containing at least one magenta coupler are dispersed on a support,
A silver halide photographic material characterized in that a mercaptan compound is contained in self-oleophilic fine particles. (2) The mercaptan compound has a log p of 2 or more.
(However, p is the partition coefficient between water and n-octatool.)
4) The silver halide photographic material described in item 4). (3) Claim No. TI1, characterized in that the mercaptan compound is represented by the following general formula [13]
Silver halogenide photographic light-sensitive material according to the general formula (l) SH (in the formula, R represents an alkyl group or a benzimidazolo group) (4), the general formula [I] The silver halide photographic material according to claim (3) JJK, wherein R is an argyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12823083A JPS6021048A (en) | 1983-07-14 | 1983-07-14 | Silver halide photosensitive material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12823083A JPS6021048A (en) | 1983-07-14 | 1983-07-14 | Silver halide photosensitive material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6021048A true JPS6021048A (en) | 1985-02-02 |
| JPH0414778B2 JPH0414778B2 (en) | 1992-03-13 |
Family
ID=14979706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12823083A Granted JPS6021048A (en) | 1983-07-14 | 1983-07-14 | Silver halide photosensitive material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6021048A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4704350A (en) * | 1985-12-25 | 1987-11-03 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| JPS63259659A (en) * | 1987-04-17 | 1988-10-26 | Fuji Photo Film Co Ltd | Color image forming method |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5339120A (en) * | 1976-09-22 | 1978-04-10 | Mitsubishi Paper Mills Ltd | Method of producing halogenated silver color emulsion |
-
1983
- 1983-07-14 JP JP12823083A patent/JPS6021048A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5339120A (en) * | 1976-09-22 | 1978-04-10 | Mitsubishi Paper Mills Ltd | Method of producing halogenated silver color emulsion |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4704350A (en) * | 1985-12-25 | 1987-11-03 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| JPS63259659A (en) * | 1987-04-17 | 1988-10-26 | Fuji Photo Film Co Ltd | Color image forming method |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0414778B2 (en) | 1992-03-13 |
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