EP0356801A1 - Lichtempfindliches photographisches Silberhalogenidmaterial - Google Patents
Lichtempfindliches photographisches Silberhalogenidmaterial Download PDFInfo
- Publication number
- EP0356801A1 EP0356801A1 EP89115029A EP89115029A EP0356801A1 EP 0356801 A1 EP0356801 A1 EP 0356801A1 EP 89115029 A EP89115029 A EP 89115029A EP 89115029 A EP89115029 A EP 89115029A EP 0356801 A1 EP0356801 A1 EP 0356801A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- silver halide
- light
- isothiazolone
- sensitive silver
- 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.)
- Withdrawn
Links
- -1 silver halide Chemical class 0.000 title claims abstract description 112
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 62
- 239000004332 silver Substances 0.000 title claims abstract description 62
- 239000000463 material Substances 0.000 title claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 239000000839 emulsion Substances 0.000 claims abstract description 23
- 239000000084 colloidal system Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 5
- 230000001737 promoting effect Effects 0.000 claims description 5
- 238000001179 sorption measurement Methods 0.000 claims description 5
- 238000009792 diffusion process Methods 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 claims description 3
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 2
- 125000005361 aryl sulfoxide group Chemical group 0.000 claims description 2
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims description 2
- 125000000626 sulfinic acid group Chemical group 0.000 claims description 2
- CVZDIUZSWUDGOP-UHFFFAOYSA-N 4,5-dichloro-2-methyl-1,2-thiazol-3-one Chemical compound CN1SC(Cl)=C(Cl)C1=O CVZDIUZSWUDGOP-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 description 27
- 239000000243 solution Substances 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 235000002566 Capsicum Nutrition 0.000 description 8
- 239000006002 Pepper Substances 0.000 description 8
- 241000722363 Piper Species 0.000 description 8
- 235000016761 Piper aduncum Nutrition 0.000 description 8
- 235000017804 Piper guineense Nutrition 0.000 description 8
- 235000008184 Piper nigrum Nutrition 0.000 description 8
- 206010070834 Sensitisation Diseases 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000008313 sensitization Effects 0.000 description 8
- 108010010803 Gelatin Proteins 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
- 239000008273 gelatin Substances 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- 235000011852 gelatine desserts Nutrition 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 239000011241 protective layer Substances 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000004442 acylamino group Chemical group 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- 150000003852 triazoles Chemical group 0.000 description 3
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- SPOCKFADQXUWGS-UHFFFAOYSA-N 3-oxo-n-propyl-1,2-thiazole-2-carboxamide Chemical compound CCCNC(=O)N1SC=CC1=O SPOCKFADQXUWGS-UHFFFAOYSA-N 0.000 description 2
- SJSJAWHHGDPBOC-UHFFFAOYSA-N 4,4-dimethyl-1-phenylpyrazolidin-3-one Chemical compound N1C(=O)C(C)(C)CN1C1=CC=CC=C1 SJSJAWHHGDPBOC-UHFFFAOYSA-N 0.000 description 2
- DSVIHYOAKPVFEH-UHFFFAOYSA-N 4-(hydroxymethyl)-4-methyl-1-phenylpyrazolidin-3-one Chemical compound N1C(=O)C(C)(CO)CN1C1=CC=CC=C1 DSVIHYOAKPVFEH-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 description 2
- WSGURAYTCUVDQL-UHFFFAOYSA-N 5-nitro-1h-indazole Chemical compound [O-][N+](=O)C1=CC=C2NN=CC2=C1 WSGURAYTCUVDQL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 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 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 2
- 235000019252 potassium sulphite Nutrition 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- 125000001391 thioamide group Chemical group 0.000 description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- GGZHVNZHFYCSEV-UHFFFAOYSA-N 1-Phenyl-5-mercaptotetrazole Chemical compound SC1=NN=NN1C1=CC=CC=C1 GGZHVNZHFYCSEV-UHFFFAOYSA-N 0.000 description 1
- NLOGTNAOFKDKBC-UHFFFAOYSA-N 1-ethyl-2-(2-methylphenyl)hydrazine Chemical compound CCNNC1=CC=CC=C1C NLOGTNAOFKDKBC-UHFFFAOYSA-N 0.000 description 1
- ANFXTILBDGTSEG-UHFFFAOYSA-N 1-methyl-4,5-dihydroimidazole Chemical compound CN1CCN=C1 ANFXTILBDGTSEG-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- AXCGIKGRPLMUDF-UHFFFAOYSA-N 2,6-dichloro-1h-1,3,5-triazin-4-one;sodium Chemical compound [Na].OC1=NC(Cl)=NC(Cl)=N1 AXCGIKGRPLMUDF-UHFFFAOYSA-N 0.000 description 1
- BDOOJCJSTQZQDM-UHFFFAOYSA-N 2-(1-phenylethyl)-1,2-thiazol-3-one Chemical compound S1C=CC(=O)N1C(C)C1=CC=CC=C1 BDOOJCJSTQZQDM-UHFFFAOYSA-N 0.000 description 1
- WDZJNLOCKSPDFK-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)-1,2-thiazol-3-one Chemical compound CC(C)(C)CC(C)(C)N1SC=CC1=O WDZJNLOCKSPDFK-UHFFFAOYSA-N 0.000 description 1
- VDYGJABWVCDOMW-UHFFFAOYSA-N 2-(2-ethoxyhexyl)-1,2-thiazol-3-one Chemical compound CCCCC(OCC)CN1SC=CC1=O VDYGJABWVCDOMW-UHFFFAOYSA-N 0.000 description 1
- HSFILUIYMMOOFQ-UHFFFAOYSA-N 2-(2-phenylethyl)-1,2-thiazol-3-one Chemical compound O=C1C=CSN1CCC1=CC=CC=C1 HSFILUIYMMOOFQ-UHFFFAOYSA-N 0.000 description 1
- KBBVCHDMBBVVCS-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-1,2-thiazol-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1N1C(=O)C=CS1 KBBVCHDMBBVVCS-UHFFFAOYSA-N 0.000 description 1
- ZDWLTASUXFDUOP-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-4-methyl-1,2-thiazol-3-one Chemical compound O=C1C(C)=CSN1C1=CC=C(Cl)C(Cl)=C1 ZDWLTASUXFDUOP-UHFFFAOYSA-N 0.000 description 1
- NFSXZGMSASBOHO-UHFFFAOYSA-N 2-(4-nitrophenyl)-1,2-thiazol-3-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C(=O)C=CS1 NFSXZGMSASBOHO-UHFFFAOYSA-N 0.000 description 1
- OPMCKYBELMAPEN-UHFFFAOYSA-N 2-(hydroxymethyl)-1,2-thiazol-3-one Chemical compound OCN1SC=CC1=O OPMCKYBELMAPEN-UHFFFAOYSA-N 0.000 description 1
- JGWRIEPVQMQWHX-UHFFFAOYSA-N 2-[(2,4-dichlorophenyl)methyl]-1,2-thiazol-3-one Chemical compound ClC1=CC(Cl)=CC=C1CN1C(=O)C=CS1 JGWRIEPVQMQWHX-UHFFFAOYSA-N 0.000 description 1
- HKJBTCVEERVODK-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-1,2-thiazol-3-one Chemical compound ClC1=CC=CC=C1CN1C(=O)C=CS1 HKJBTCVEERVODK-UHFFFAOYSA-N 0.000 description 1
- YQMPKMMIBGGAJX-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methyl]-1,2-thiazol-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1C(=O)C=CS1 YQMPKMMIBGGAJX-UHFFFAOYSA-N 0.000 description 1
- ZJJDXJDCYJWVAY-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methyl]-1,2-thiazol-3-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C=CS1 ZJJDXJDCYJWVAY-UHFFFAOYSA-N 0.000 description 1
- VZZAUYDBJJHFFD-UHFFFAOYSA-N 2-[(4-methylphenyl)methyl]-1,2-thiazol-3-one Chemical compound C1=CC(C)=CC=C1CN1C(=O)C=CS1 VZZAUYDBJJHFFD-UHFFFAOYSA-N 0.000 description 1
- BAPMGYBFLAMFTH-UHFFFAOYSA-N 2-benzyl-1,2-thiazol-3-one;2-chloroacetic acid Chemical compound OC(=O)CCl.O=C1C=CSN1CC1=CC=CC=C1 BAPMGYBFLAMFTH-UHFFFAOYSA-N 0.000 description 1
- JXDBZXGTFLLJPZ-UHFFFAOYSA-N 2-benzyl-1,2-thiazol-3-one;hydrochloride Chemical compound Cl.O=C1C=CSN1CC1=CC=CC=C1 JXDBZXGTFLLJPZ-UHFFFAOYSA-N 0.000 description 1
- JWPUURGEVMUUAB-UHFFFAOYSA-N 2-benzyl-4,5-dichloro-1,2-thiazol-3-one Chemical compound O=C1C(Cl)=C(Cl)SN1CC1=CC=CC=C1 JWPUURGEVMUUAB-UHFFFAOYSA-N 0.000 description 1
- BXQOWUSZAWCFIL-UHFFFAOYSA-N 2-benzyl-5-chloro-1,2-thiazol-3-one Chemical compound S1C(Cl)=CC(=O)N1CC1=CC=CC=C1 BXQOWUSZAWCFIL-UHFFFAOYSA-N 0.000 description 1
- CRTPTZMJMAGFEQ-UHFFFAOYSA-N 2-butyl-1,2-thiazol-3-one Chemical compound CCCCN1SC=CC1=O CRTPTZMJMAGFEQ-UHFFFAOYSA-N 0.000 description 1
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- WGYAVEROXSCCDD-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxo-1,2-thiazole-2-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)N1C(=O)C=CS1 WGYAVEROXSCCDD-UHFFFAOYSA-N 0.000 description 1
- ZLJITXLJFQVLKX-UHFFFAOYSA-N n-(3-chlorophenyl)-4-cyano-5-methylsulfanyl-3-oxo-1,2-thiazole-2-carboxamide Chemical compound O=C1C(C#N)=C(SC)SN1C(=O)NC1=CC=CC(Cl)=C1 ZLJITXLJFQVLKX-UHFFFAOYSA-N 0.000 description 1
- VPGPOJYDQBKTOH-UHFFFAOYSA-N n-(3-chlorophenyl)-5-methyl-3-oxo-1,2-thiazole-2-carboxamide Chemical compound S1C(C)=CC(=O)N1C(=O)NC1=CC=CC(Cl)=C1 VPGPOJYDQBKTOH-UHFFFAOYSA-N 0.000 description 1
- JIHBJVYDJRUMEP-UHFFFAOYSA-N n-(3-nitrophenyl)-3-oxo-1,2-thiazole-2-carboxamide Chemical compound [O-][N+](=O)C1=CC=CC(NC(=O)N2C(C=CS2)=O)=C1 JIHBJVYDJRUMEP-UHFFFAOYSA-N 0.000 description 1
- HMJKGINKCNRDPP-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-oxo-1,2-thiazole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)N1C(=O)C=CS1 HMJKGINKCNRDPP-UHFFFAOYSA-N 0.000 description 1
- IBRJHJANXBOOQC-UHFFFAOYSA-N n-(4-nitrophenyl)-3-oxo-1,2-thiazole-2-carboxamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)N1C(=O)C=CS1 IBRJHJANXBOOQC-UHFFFAOYSA-N 0.000 description 1
- HQPSBTFNKVNNSM-UHFFFAOYSA-N n-butyl-3-oxo-1,2-thiazole-2-carboxamide Chemical compound CCCCNC(=O)N1SC=CC1=O HQPSBTFNKVNNSM-UHFFFAOYSA-N 0.000 description 1
- NKMSQSZVYLBQRG-UHFFFAOYSA-N n-dodecyl-3-oxo-1,2-thiazole-2-carboxamide Chemical compound CCCCCCCCCCCCNC(=O)N1SC=CC1=O NKMSQSZVYLBQRG-UHFFFAOYSA-N 0.000 description 1
- QDSRDMJXSQGYGM-UHFFFAOYSA-N n-ethyl-3-oxo-1,2-thiazole-2-carboxamide Chemical compound CCNC(=O)N1SC=CC1=O QDSRDMJXSQGYGM-UHFFFAOYSA-N 0.000 description 1
- PCKGHRKNRYYUJY-UHFFFAOYSA-N n-ethyl-5-methyl-3-oxo-1,2-thiazole-2-carbothioamide Chemical compound CCNC(=S)N1SC(C)=CC1=O PCKGHRKNRYYUJY-UHFFFAOYSA-N 0.000 description 1
- XPOIDNGCJWQQCT-UHFFFAOYSA-N n-ethyl-5-methyl-3-oxo-1,2-thiazole-2-carboxamide Chemical compound CCNC(=O)N1SC(C)=CC1=O XPOIDNGCJWQQCT-UHFFFAOYSA-N 0.000 description 1
- FYXNYYCUQPPCNJ-UHFFFAOYSA-N n-methyl-3-oxo-1,2-thiazole-2-carbothioamide Chemical compound CNC(=S)N1SC=CC1=O FYXNYYCUQPPCNJ-UHFFFAOYSA-N 0.000 description 1
- ARBGYZLXHACKCD-UHFFFAOYSA-N n-methyl-3-oxo-1,2-thiazole-2-carboxamide Chemical compound CNC(=O)N1SC=CC1=O ARBGYZLXHACKCD-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000003452 oxalyl group Chemical group *C(=O)C(*)=O 0.000 description 1
- CELWCAITJAEQNL-UHFFFAOYSA-N oxan-2-ol Chemical compound OC1CCCCO1 CELWCAITJAEQNL-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical class [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- NDGRWYRVNANFNB-UHFFFAOYSA-N pyrazolidin-3-one Chemical class O=C1CCNN1 NDGRWYRVNANFNB-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- DZCAZXAJPZCSCU-UHFFFAOYSA-K sodium nitrilotriacetate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O DZCAZXAJPZCSCU-UHFFFAOYSA-K 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/061—Hydrazine compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/37—Antiseptic agents
Definitions
- This invention relates to a light-sensitive silver halide photographic material which gives images of high contrast, more particularly to improvement of trouble generated in high contrasting technique with a hydrazide compound.
- printing sensitive material light-sensitive silver halide photographic material for printing
- printing sensitive material has been generally endowed with the so called “lith development” processing aptitude for accompolishing high quality.
- lith development it is impossible in mechanism to contain sulfite ion which is the preservative at high concentration in the development processing solution, and therefore stability of the developer is very poor, as is well known to those skilled in the art.
- hydrazide compounds can obtain images of very high contrast.
- development processing solution may suffer from fog generation, etc. undesirable in photographic performance when no adequate development supplementing agent is supplemented, but in the method by use of hydrazide, even when the fatigue degree of the development processing solution is not so great, generation of black dots like black sesame (hereinafter called pepper fog) is seen at the unexposed portion, for example, between the dots during halftoning by use of a contact screen in printing sensitive material, whereby a trouble may be caused to occur which can be a vital defect in commercial value.
- pepper fog black dots like black sesame
- the present inventors have studied intensively and consequently could develop a light-sensitive silver halide photographic material which does not impair high contrast while inhibiting the fog including pepper fog which is the drawback of the tone hardening technique by use of a hydrazide compound.
- a first object of the present invention is to provide a light-sensitive silver halide photographic material capable of forming an image of high contrast stably by use of a hydrazide compound.
- a second object of the present invention is to provide a light-sensitive silver halide photographic material with high contrast without generation of fog including pepper fog.
- a light-sensitive silver halide photographic material having a hydrophilic colloid layer containing at least one layer of a light-sensitive silver halide emulsion layer provided on a support, wherein a hydrazide derivative is contained in said light-sensitive silver halide emulsion layer, and the above hydrophilic colloid layer contains at least one of the compounds represented by Formulae [II] and [III] shown below: wherein R represents hydrogen atom, a straight or branched alkyl group, a cyclic alkyl group, an alkenyl group, an aralkyl group, an aryl group, a heterocyclic group, an alkylamide group, an arylamide group, an alkylthioamide group, an arylthioamide group, an alkylsulfonamide group or an arylsulfonamide group, R 2 and R 3 each represent hydrogen atom, a halogen atom, an alkyl group, a
- the hydrazide derivative to be used in the present invention may include the compounds represented by the following formulae [I -a], [I - b] and [I - c]. wherein R 1 and R 2 each represent an aryl group or a heterocyclic group, R represents a divalent organic linking group, n is 0 to 6, m is 0 or 1, and when n is 2 or more, respective R's may be either the same or different).
- R 21 represents an aliphatic group, an aromatic group or a heterocyclic group
- R 22 represents hydrogen atom, an alkoxy group which may be substituted, a heterocyclic oxy group, an amino group or an aryloxy group
- P 1 and P 2 each represent hydrogen atom, an acyl group or a sulfinic acid group.
- Ar represents an aryl group containing at least one of diffusion resistant group or silver halide adsorption promoting group
- R 31 represents a substituted alkyl group.
- R, and R 2 each represent an aryl group or a heterocyclic group
- R represents a divalent organic linking group
- n represents 0 to 6 and m represents 0 or 1.
- the aryl group represented by R, and R 2 may include phenyl group, naphthyl group, and the heterocyclic group represented by R, and R 2 may include pyridyl group, benzothiazolyl group, quinolyl group, thienyl group, etc., but R, and R 2 may be preferably aryl groups.
- the aryl group or heterocyclic group represented by R 1 and R 2 can introduce various substituents therein. Examples of substituents may include halogen atoms (e.g. chlorine, fluorine, etc.), alkyl groups (e.g. methyl, ethyl, dodecyl, etc.), alkoxy groups (e.g.
- acylamino groups e.g. acetylamino, pivalylamino, benzoylamino, tetradecanoylamino, a-(2,4-di-t-amylphenoxy) butyrylamino, etc. ⁇
- sulfonylamino groups e.g. methanesulfonylamino, butanesulfonylamino, dodecanesulfonylamino, ben- zenesulfonylamino, etc.
- urea groups e.g.
- phenylurea, ethylurea, etc. thiourea groups (e.g. phenylthiourea, ethylthiourea, etc.), hydroxy group, amino group, alkylamino groups (e.g. methylamino, dimethylamino, etc.), carboxy group, alkoxycarbonyl groups (e.g. ethoxycarbonyl), carbamoyl group, sulfo group and so on.
- Examples of the divalent organic linking group represented by R may include alkylene groups (e.g. methylene, ethylene, trimethylene, tetramethylene, etc.), arylene groups (e.g.
- phenylene, naphthylene, etc. aralkylene groups, etc.
- the alkylene group may contain oxy group, thio group,seleno group, carbonyl group, (Rs represents hydrogen atom, an alkyl group, an aryl group), sulfonyl group, etc. in the bond.
- R represents hydrogen atom, an alkyl group, an aryl group
- sulfonyl group etc. in the bond.
- Into the group represented by R can be introduced various substituents.
- substituents may include -CONHNHR 4 . (R 4 . has the same meaning as R 1 and R 2 as described above), alkyl groups, alkoxy groups, halogen atoms, hydroxy group, carboxy group, acyl groups, aryl groups, etc.
- R may be preferably a alkylene group.
- the aliphatic group represented by R 21 may be preferably one having 6 or more carbon atoms, particularly a straight, branched or cyclic alkyl group having 8 to 50 carbon atoms.
- the branched alkyl group may be cyclized so as to form a saturated hetero ring containing one or more hetero atoms.
- the alkyl group may have substituent such as aryl group, alkoxy group, sulfoxy group, etc.
- the aromatic group represented by R 21 is a monocyclic or bicyclic aryl group or unsaturated heterocyclic group.
- the unsaturated heterocyclic group may be condensed with the monocyclic or bicyclic group to form a heteroaryl group.
- benzene ring there may be included benzene ring, naphthalene ring, pyridine ring, pyrimidine group, imidazole ring, pyrazole ring, quinoline ring, isoquinoline ring, benzimidazole ring, thiazole ring, benzothiazole ring, etc., but amount them those containing benzene ring are preferred.
- R 21 particularly preferred is an aryl group.
- the aryl group or unsaturated heterocyclic group represented by R 21 may be substituted, and representative substituents may include straight, branched or cyclic alkyl groups (preferably monocyclic or bicyclic ones with an alkyl moiety having 1 to 20 carbon atoms), alkoxy groups (having preferably 1 to 20 carbon atoms), substituted amino groups (preferably amino groups substituted with alkyl groups having 1 to 20 carbon atoms), acylamino groups (having preferably 2 to 30 carbon atoms), sulfonamide groups (having preferably 1 to 30 carbon atoms), ureido groups (having preferably 1 to 30 carbon atoms) and others.
- substituents may include straight, branched or cyclic alkyl groups (preferably monocyclic or bicyclic ones with an alkyl moiety having 1 to 20 carbon atoms), alkoxy groups (having preferably 1 to 20 carbon atoms), substituted amino groups (preferably amino groups substituted with alkyl groups having 1 to 20 carbon
- the alkoxy group which may be substituted may have 1 to 20 carbon atoms and may be substituted with halogen atoms, aryl groups, etc.
- the aryloxy group or the heterocyclic oxy group which may be also substituted may be preferably monocyclic, and the substituent may include halogen atoms, alkyl groups, alkoxy group, cyano group, etc.
- R 22 Of the groups represented by R 22 , preferable are alkoxy groups or amino groups which may be also substituted.
- a 1 and A 2 in the group group may be an alkyl group, alkoxy group which may be substituted, or a cyclic structure containing -0-, -S-, -N- group bond.
- R 22 cannot be hydrazino group.
- R 21 or R 22 in Formula [I - b] may be one having a ballast group conventionally used in the immobile additive for photography such as coupler, etc. incorporated therein.
- the ballast group is a group having 8 or more carbon atoms relatively inert to photographic characteristic, and can be chosen from, for example, alkyl groups, alkoxy groups, phenyl groups, alkylphenyl groups, phenoxy groups, alkylphenoxy groups, etc.
- R 21 or R 22 in Formula [I - b] may be also one having a group for strengthening adsorption to the surface of silver halide grains incorporated therein.
- adsorptive groups there may be included the groups as disclosed in U.S. Patent 4,355,105 such as thiourea group, heterocyclic thioamide group, mercaptoheterocyclic group, triazole group, etc.
- the compounds represented by the group [I - b] are particularly preferable.
- Represenatative compounds represented by the above Formulae [I - b] and [I - b - a] are shown below.
- Ar represents an aryl group containing at least one of diffusion resistant groups or silver halide adsorption promoting groups, and as the diffusion resistant group, a ballast group conventionally used in immobile additives for photography such as coupler, etc. is preferable.
- the ballast group is a group having 8 or more carbon atoms relatively inert to photographic characteristic, and can be chosen from, for example, alkyl groups, alkoxy groups, phenyl groups, alkylphenyl groups, phenoxy groups, alkylphenoxy groups, etc.
- silver halide adsorption promoting group there may be included the groups as disclosed in U.S. Patent 4,385,108 such as thiourea group, thiourethane group, heterocyclic thioamide group, mercaptoheterocyclic group, triazole group, etc.
- R 3 represents a substituted alkyl group, and the alkyl group may be a straight, branched or cyclic alkyl group, including methyl, ethyl, propyl, butyl, isopropyl, pentyl, cyclohexyl and the like.
- alkoxy e.g. methoxy, ethoxy
- aryloxy e.g. phenoxy, p-chlorophenoxy
- heterocyclic oxy e.g. pyridyloxy
- mercapto alkylthio (e.g. methylthio, ethylthio), arylthio (e.g. phenylthio, p-chlorophenylthio), heterocyclic thio (e.g. pyridylthio, pyrimidylthio, thiadiazolylthio), alkylsulfonyl (e.g.
- acetyloxy acetyloxy, benzoyloxy
- alkylaminocarbonyloxy e.g. methylaminocarbonyloxy
- arylaminocar- bonyloxy e.g. phenylaminocarbonyloxy
- sulfo sulfamoyl
- alkylsulfamoyl e.g. methylsulfamoyl
- arylsulfamoyl e.g. phenylsulfamoyl
- the hydrogen atom of hydrazide may be also substituted with a substituent such as sulfonyl group (e.g. methanesulfonyl, toluenesulfonyl), acyl group (e.g. acetyl, trifluoroacetyl), oxalyl group (e.g. ethoxalyl), etc.
- sulfonyl group e.g. methanesulfonyl, toluenesulfonyl
- acyl group e.g. acetyl, trifluoroacetyl
- oxalyl group e.g. ethoxalyl
- the amount of the compounds of Formulae [I - a], [I - b] and [I - c] contained in the light-sensitive silver halide material of the present invention should be preferably within the range of from 5 x 10- 7 to 5 x 10 -1 mol, more preferably 1 x 10- 5 to 1 x 10- 2 mol, per mol of silver halide contained in the light-sensitive silver halide photographic material.
- R 1 represents hydrogen atom, a straight or branched alkyl group, a cyclic alkyl group, an alkenyl group, an aralykyl group, an aryl group, a heterocyclic group, an alkylamino group, an arylamide groups, an alkylthioamide group, an arylthioamide group, an alkylsulfoamide group, an arylsulfoamide group;
- R 2 , R 3 each represent hydrogen atom, a halogen atom, an alkyl group, a cyclic alkyl group, an aryl group, a cyano group, an alkylthio group, an arylthio group, an alkylsulfoxide group, an alkylsulfonyl group, a heterocyclic group.
- the above alkyl group, cyclic alkyl group, alkenyl group, heteocyclic group, aralkyl group and aryl group may have substitu
- the alkyl group and the alkenyl group may have 1 to 36, more preferably 1 to 18 carbon atoms.
- the cyclic alkyl group may have 3 to 12, more preferably 3 to 6 carbon atoms.
- These alkyl groups, alkenyl groups, cyclic alkyl groups, aralkyl groups, aryl groups, heterocyclic groups may have substituents, and the substituent may be chosen from halogen atom, nitro, cyano, thiocyano, aryl, alkoxy, aryloxy, carboxy, sulfoxy, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, sulfo, acyloxy, sufamoyl, carbamoyl, acylamino, diacylamino, ureido, thioureido, urethane, thiourethane, sulfonamide, heterocyclic group
- the alkyl group may have 1 to 18, more preferably 1 to 9 carbon atoms.
- the cyclic alkyl group may have 3 to 12, more preferably 3 to 6 carbon atoms.
- These alkyl groups, cyclic alkyl groups and aryl groups may have substituents, and the substituent may include halogen atom, nitro group, sulfone group, aryl group, hydroxy group, etc.
- R 1 represents hydrogen, a lower alkyl group or hydroxymethyl group
- R 2 represents hydrogen or a lower alkyl group
- R 1 represents hydrogen, a lower alkyl group or hydroxymethyl group
- R 2 represents hydrogen or a lower alkyl group
- the lower alkyl group one having 1 to 5 carbon atoms, particularly 1 carbon atom, is preferred.
- the compound represented by Formulae [II] or [III] may be used in an amount preferably within the range of 1 x 10- 3 to 10% by weight, preferably 1 x 10- 3 to 3 % by weight, more preferably 5 x 10 -3 to 3% by weight, based on the hydrophilic colloid.
- the above range may be more or less varied depending on the kind of the light-sensitive silver halide photograpic material, the layer into which it is added, the coating method, etc., as a matter of course.
- the compound of the present invention may be dissolved in a solvent which has no deleterious influence on photographic performance, chosen from water and organic solvents such as methanol, isopropanol, acetone, etc. and added as the solution into the hydrophilic colloid, or coated on the protective layer or incorporated by dipping into a sterilizing agent solution.
- a solvent which has no deleterious influence on photographic performance chosen from water and organic solvents such as methanol, isopropanol, acetone, etc.
- a solvent which the compound is dissolved in a high boiling solvent, a low boiling solvent or a solvent mixture of both, then emulsified in the presence of a surfactant and then added into a solution containing the hydrophilic colloid or further coated on the protective layer, etc.
- the silver halide to be used in the present invention may be either one of silver chlorobromide, silver chloroiodobromide, silver iodobromide.
- the grain size of the silver halide is not particularly limited, but one with a mean grain size of 0.5 nm or less may be preferable, and the so called mono-dispersed grains with 90% or more of the total grains falling within ⁇ 40% from the mean grain size as the center are preferred.
- the silver halide grains may have a crystal habit which may be either cubic, tetradecahedral and octahedral, and may be also the tablet type grain as disclosed in Japanese Unexamined Patent Publication No. 108525/1983.
- the silver halide grains in the silver halide emulsion layer of the present invention may be prepared according to any one of the single jet method such as the normal mixing method, the reverse mixing method, etc. or the double jet method according to the simultaneous mixing method, more preferably the simultaneous mixing method. Also, any of the ammonia method, the neutral method, the acidic method or the modified ammonia method as disclosed in Japanese Patent Publication No. 3232/1983, more preferably the acidic method or the neutral method, may be employed.
- metal atoms such as iridium, rhodium, osmium, bismuth, cobalt, nickel, ruthenium, iron, copper, zinc, lead, cadmium, etc. may be contained.
- the content may be preferably within the range of 10- 8 to 10- 5 mol per mol of silver halide.
- the silver halide grains may be preferably of the surface latent image type.
- the silver halide photographic emulsion in the silver halide emulsion layer according to the present invention can be applied with chemical sensitization.
- the chemical sensitization method is inclusive of sulfur sensitization, reduction sensitization and noble metal sensitization, but in the present invention, it is preferable to perform chemical sensitization by sulfur sensitization alone.
- sulfur sensitizer other than sulfur compounds contained in gelatin, various sulfur compounds such as thiosulfates, thioureas, thiazoles, rhodanines, etc. can be employed, and specifically the sulfur sensitizers as disclosed in U.S. Patents 1574944, 2410689, 2728668 and Japanese Patent Publication No. 11892/1984 can be employed.
- the silver halide photographic emulsion of the present invention can be imparted with photosensitivities to the respective desired photosensitive wavelength regions.
- optical sensitization may be also effected by use of one or two or more kinds of spectral sensitizers.
- optically spectral sensitizers which can be used advantageously in the present invention may include cyanines, car- bocyanines, melocyanines, trinucieus or tetranucleus melocyanines, trinucleus or tetranucleus cyanines, styryls, holopolar cyanines, hemine cyanines, oxonols, hemioxonols, etc., and these optically spectral sensitizers should preferably contain a basic group such as thiazoline, thiazole, etc.
- nucleus such as rhodanine, thiohydantoin, oxsazolidinedione, barbituric acid, thiobarbituric acid, pyrazolone, etc. as a part of the structure as the nitrogen containing heterocyclic nucleus, and such nucleus can be also substituted with alkyl, hydroxyalkylhalogen, phenyl, cyano, aikoxy, and also these optically spectral sensitizers may be condensed with carbon ring or heterocyclic ring.
- the silver halide photographic emulsion of the present invention it is possible to add stabilizers such as tetrazaindenes, antifoggants such as triazoles, tetrazoles, covering power enhancers, antiirradiation agents such as oxanol dyes, dialkylaminobenzylidene dyes, etc., humectants such as polymer latices, and other additives used for photographic emulsions in general such as extenders, film hardeners to be used in combination outside of the present invention.
- stabilizers such as tetrazaindenes, antifoggants such as triazoles, tetrazoles, covering power enhancers, antiirradiation agents such as oxanol dyes, dialkylaminobenzylidene dyes, etc., humectants such as polymer latices, and other additives used for photographic emulsions in general such as extenders, film hardeners
- the support of the light-sensitive silver halide photographic material of the present invention may be one conventionally used such as polyester base, TAC base, baryta paper, laminated paper, glass plate, etc.
- the developer to be used for the light-sensitive silver halide photographic material of the present invention there can be used either one of the developer used for light-sensitive silver halide photographic materials in general and the lith developer.
- the developing agent in these developers may include dihydroxybenzenes such as hydroquinone, chlorohydroquinone, catechol; 3-pyrazolidones such as 1-phenyl-3-pyrazolidone, 1-phenyl-4,4-dimethyl-3-pyrazolidone, 1-phenyl-4-methyl-3-pyrazolidone, 1-phenyl-4-methyl-4-hydroxymethyl-3-pyrazolidone; and further p-aminophenols such as N-methyl-p-aminophenol, N-(4-hydroxyphenyl)glycine; p-phenylenediamines such as Q-methanesulfonamide ester, ethylaminotoluidine, N,N-diethyl-p-phenylenediamine; and ascorbic acids, etc., and it
- the developer can be constituted by adding otherwise preservatives such as sodium sulfite, potassium sulfite, formaldehyde, sodium hydrogen sulfite, hydroxylamine, ethylene urea; developing inhibitors of inorganic salts such as sodium bromide, potassium bromide, potassium iodide; at least one organic inhibitor such as 1-phenyl-5-mercaptotetrazole, 5-nitrobenzimidazole, 5-nitrobenzotriazole, 5-nitroindazole, 5-methylbenzotriazole, 4-thiazolin-2-thione, etc.; alkali agents such as sodium hydroxide, potassium hydroxide, etc.; alkanolamines having development accelerating effect such as diethanolamine, triethanolamine, 3-diethylamine-1-propanol, 2-methylamino-1-ethanol, 3-diethylamino-1,2-propanediol, diisopropylamine, 5-amino-1-pentanol, 6-amino-1-
- the pH of the developer is not particularly limited, but may be preferably within the range of pH 9 to 13.
- An example of the construction of the preferable developer for developing the light-sensitive silver halide photographic material of the present invention is as follows. That is, it is a developer prepared by adding 20 to 60 g/liter of hydroquinone and 0.1 to 2 g/liter of 1-phenyl-4-methyl-4-hydroxymethyl-3-pyrazolidone or 0.1 to 2 g/liter of 1-phenyl-4,4-dimethyl-3-pyrazolidone as the developing agent, 10 to 200 g/liter of sodium sulfite or 10 to 200 g/liter of potassium sulfite as the developer preservative, 1 to 10 g of sodium bromide or potassium bromide as the developing inhibitor of inorganic salt, 1 to 50 g/liter of alkanolamines having development accelerating effect, 0.05 to 2 g/liter of 5-methylbenzotriazole or 0.01 to 2 g/liter of 5-nitroindazole as the organic inhibitor, 1 to 50 g/liter of sodium carbonate or 10 to 800 ml/liter of an a
- the light-sensitive silver halide photographic material of the present ivnention is developed with the developer as described above, and then the image is fixed via the process of fixing, water washing and drying.
- the developing temperature and the developing time in the developing process are not particularly limited, but the developing temperature may be preferably in the range of 20 to 45 C, and the developing time in the range of 15 seconds to 200 seconds.
- aqueous gelatin solution maintained at 40 °C were added simultaneously over 60 minutes an aqueous silver nitrate solution and an aqueous halide solution (KBr 40 mol%, NaCI 60 mol%) according to the controlled double jet method while maintaining pH at 3.0 and pAg at 7.7 to prepare a mono-dispersed silver chlorobromide emulsion with a mean grain size of 0.30 ⁇ m.
- the emulsion was desalted and washed with water in conventional manners, and then 15 mg of sodium thiosulfate was per mol of silver chlorobromide, followed by chemical ripening at 60 ° C for 60 minutes.
- aqueous gelatin solution containing an aqueous sodium 1-decyl-2-(3-isopentyl)succinate-2-sulfonate solution, a methyl methacrylate copolymer with a mean particle size of 3.0 ⁇ m as the matte agent, and 2-hydroxy-4,6-dichloro-1,3,5-triazine sodium salt as the film hardener to prepare a coating solution for protective layer, which was coated by simultaneous overlaying together with the above emulsion coating solution on a PET base, followed by drying.
- aqueous sodium 1-decyl-2-(3-isopentyl)succinate-2-sulfonate solution a methyl methacrylate copolymer with a mean particle size of 3.0 ⁇ m as the matte agent
- 2-hydroxy-4,6-dichloro-1,3,5-triazine sodium salt as the film hardener
- the amount of gelatin attached was 2.5 g/m 2 in the emulsion layer, 1.0 g/m 2 in the protective layer, the amount of AgX grains attaches was 3.5 g/m 2 as calculated on silver, the amount of the butyl acrylate latex polymer attached was 2 g/m 2 , the amount of the matte agent attached was 30 mg/m 2 , the amount of the film hardener attached was 2 g/100 g gelatin based on the amount of gelatin attached of the the emulsion layer and the protective layer inclusive.
- the compounds (a) - (b) shown below were employed as the comparative compound added in the silver halide emulsion layer.
- the above composition A and the composition B were dissolved in this order in 500 ml of water, and made up to one liter before use.
- the pH of the fixer was adjusted to 6 with acetic acid.
- a light-sensitive silver halide photographic material which is extremely high in contrast, and also improved in generation of peper fog without impairing tone hardening could be provided.
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- Spectroscopy & Molecular Physics (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP205229/88 | 1988-08-17 | ||
| JP20522988A JPH0253047A (ja) | 1988-08-17 | 1988-08-17 | ハロゲン化銀写真感光材料 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0356801A1 true EP0356801A1 (de) | 1990-03-07 |
Family
ID=16503543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP89115029A Withdrawn EP0356801A1 (de) | 1988-08-17 | 1989-08-15 | Lichtempfindliches photographisches Silberhalogenidmaterial |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0356801A1 (de) |
| JP (1) | JPH0253047A (de) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0449563A1 (de) * | 1990-03-30 | 1991-10-02 | Konica Corporation | Photographisches Silberhalogenidmaterial |
| US5126227A (en) * | 1990-10-17 | 1992-06-30 | Eastman Kodak Company | High contrast photographic elements containing ballasted hydrophobic isothioureas |
| US5196292A (en) * | 1991-10-17 | 1993-03-23 | Eastman Kodak Company | Nucleated high contrast photographic elements containing ballasted thioether isothioureas to inhibit pepper fog and restrain image spread |
| US5232818A (en) * | 1991-07-25 | 1993-08-03 | Eastman Kodak Company | Nucleated high contrast photographic elements containing thioether compounds to inhibit pepper fog and restrain image spread |
| EP0578170A1 (de) * | 1992-07-07 | 1994-01-12 | Fuji Photo Film Co., Ltd. | Photographisches Bildverarbeitungsverfahren |
| EP0618486A3 (de) * | 1993-03-31 | 1994-11-23 | Fuji Photo Film Co Ltd | Photographisches Silberhalogenidmaterial. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0090584A2 (de) * | 1982-03-27 | 1983-10-05 | Konica Corporation | Lichtempfindliches photographisches Silberhalogenidaufzeichnungsmaterial |
-
1988
- 1988-08-17 JP JP20522988A patent/JPH0253047A/ja active Pending
-
1989
- 1989-08-15 EP EP89115029A patent/EP0356801A1/de not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0090584A2 (de) * | 1982-03-27 | 1983-10-05 | Konica Corporation | Lichtempfindliches photographisches Silberhalogenidaufzeichnungsmaterial |
Non-Patent Citations (2)
| Title |
|---|
| PATENT ABSTRACTS OF JAPAN, vol. 9, no. 273 (P-401)[1996], 30th October 1985; & JP-A-60 119 547 (KONISHIROKU SHASHIN KOGYO K.K.) 27-06-1985 * |
| RESEARCH DISCLOSURE, no. 235, November 1983, pages 346-352, disclosure no. 23510, Havant Hampshire, GB; "Development nucleation by hydrazine and hydrazine derivatives" * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0449563A1 (de) * | 1990-03-30 | 1991-10-02 | Konica Corporation | Photographisches Silberhalogenidmaterial |
| US5126227A (en) * | 1990-10-17 | 1992-06-30 | Eastman Kodak Company | High contrast photographic elements containing ballasted hydrophobic isothioureas |
| US5232818A (en) * | 1991-07-25 | 1993-08-03 | Eastman Kodak Company | Nucleated high contrast photographic elements containing thioether compounds to inhibit pepper fog and restrain image spread |
| US5196292A (en) * | 1991-10-17 | 1993-03-23 | Eastman Kodak Company | Nucleated high contrast photographic elements containing ballasted thioether isothioureas to inhibit pepper fog and restrain image spread |
| EP0578170A1 (de) * | 1992-07-07 | 1994-01-12 | Fuji Photo Film Co., Ltd. | Photographisches Bildverarbeitungsverfahren |
| US5340704A (en) * | 1992-07-07 | 1994-08-23 | Fuji Photo Film Co., Ltd. | Method for processing a silver halide photographic material |
| EP0618486A3 (de) * | 1993-03-31 | 1994-11-23 | Fuji Photo Film Co Ltd | Photographisches Silberhalogenidmaterial. |
| US5468592A (en) * | 1993-03-31 | 1995-11-21 | Fuji Photo Film Co. Ltd. | Silver halide photographic material |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0253047A (ja) | 1990-02-22 |
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