EP0690344A1 - Matériau photographique à couleurs à l'halogénure d'argent sensible à la lumière - Google Patents

Matériau photographique à couleurs à l'halogénure d'argent sensible à la lumière Download PDF

Info

Publication number: EP0690344A1
Authority: EP; European Patent Office
Prior art keywords: group; silver halide; formula; color photographic; photographic light
Prior art date: 1994-06-29
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP95304580A

Other languages

German (de)

English (en)

Inventor

Shuichi Sugita

Akira Onodera

Tomio Horiuti

Chiyoko Komatsu

Hidenobu Ohya

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Konica Minolta Inc

Original Assignee

Konica Minolta Inc

Priority date (The priority date 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 date listed.)

1994-06-29

Filing date

1995-06-29

Publication date

1996-01-03

1994-06-29 Priority claimed from JP14808194A external-priority patent/JPH0815833A/ja

1994-09-21 Priority claimed from JP22682394A external-priority patent/JP3254455B2/ja

1995-06-29 Application filed by Konica Minolta Inc filed Critical Konica Minolta Inc

1996-01-03 Publication of EP0690344A1 publication Critical patent/EP0690344A1/fr

Status Withdrawn legal-status Critical Current

Links

-1 Silver halide Chemical class 0.000 title claims abstract description 105
229910052709 silver Inorganic materials 0.000 title claims abstract description 75
239000004332 silver Substances 0.000 title claims abstract description 75
239000000463 material Substances 0.000 title claims abstract description 37
150000001875 compounds Chemical class 0.000 claims abstract description 45
239000000839 emulsion Substances 0.000 claims abstract description 39
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
125000001424 substituent group Chemical group 0.000 claims abstract description 32
125000001931 aliphatic group Chemical group 0.000 claims abstract description 30
125000003118 aryl group Chemical group 0.000 claims abstract description 27
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 18
125000000217 alkyl group Chemical group 0.000 claims description 28
125000000547 substituted alkyl group Chemical group 0.000 claims description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 15
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
125000004442 acylamino group Chemical group 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 11
125000006165 cyclic alkyl group Chemical group 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 10
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000003282 alkyl amino group Chemical group 0.000 claims description 5
125000001769 aryl amino group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
239000000539 dimer Substances 0.000 claims description 2
239000010410 layer Substances 0.000 description 44
239000000243 solution Substances 0.000 description 37
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000013078 crystal Substances 0.000 description 14
229940093499 ethyl acetate Drugs 0.000 description 12
235000019439 ethyl acetate Nutrition 0.000 description 12
238000010521 absorption reaction Methods 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
238000004061 bleaching Methods 0.000 description 10
108010010803 Gelatin Proteins 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
125000004423 acyloxy group Chemical group 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
239000008273 gelatin Substances 0.000 description 8
229920000159 gelatin Polymers 0.000 description 8
235000019322 gelatine Nutrition 0.000 description 8
235000011852 gelatine desserts Nutrition 0.000 description 8
125000005843 halogen group Chemical group 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 8
238000000034 method Methods 0.000 description 7
230000035945 sensitivity Effects 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000004104 aryloxy group Chemical group 0.000 description 6
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
238000010992 reflux Methods 0.000 description 6
238000010898 silica gel chromatography Methods 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 5
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 5
125000005110 aryl thio group Chemical group 0.000 description 5
125000004093 cyano group Chemical group *C#N 0.000 description 5
238000001035 drying Methods 0.000 description 5
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
239000003921 oil Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
238000007670 refining Methods 0.000 description 5
238000005406 washing Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
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 4
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
229910021612 Silver iodide Inorganic materials 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000012043 crude product Substances 0.000 description 4
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 4
238000002474 experimental method Methods 0.000 description 4
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 4
239000000203 mixture Substances 0.000 description 4
230000008569 process Effects 0.000 description 4
239000011241 protective layer Substances 0.000 description 4
229940045105 silver iodide Drugs 0.000 description 4
239000000126 substance Substances 0.000 description 4
VOJUXHHACRXLTD-UHFFFAOYSA-N 1,4-dihydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC(O)=C21 VOJUXHHACRXLTD-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
239000007844 bleaching agent Substances 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
238000004321 preservation Methods 0.000 description 3
230000003595 spectral effect Effects 0.000 description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
125000004149 thio group Chemical group *S* 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical group NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
239000002250 absorbent Substances 0.000 description 2
230000002745 absorbent Effects 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000008901 benefit Effects 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000005521 carbonamide group Chemical group 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 2
125000002704 decyl 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])* 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
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 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
150000004780 naphthols Chemical class 0.000 description 2
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000003452 oxalyl group Chemical group *C(=O)C(*)=O 0.000 description 2
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
239000004848 polyfunctional curative Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
PVGJJUSAFXAEMD-UHFFFAOYSA-N 1-(2-methylpropoxy)-2-nitro-4-(2,4,4-trimethylpentan-2-yl)benzene Chemical compound CC(C)COC1=CC=C(C(C)(C)CC(C)(C)C)C=C1[N+]([O-])=O PVGJJUSAFXAEMD-UHFFFAOYSA-N 0.000 description 1
YQHPSRBZZDBQKI-UHFFFAOYSA-N 1-(2-methylpropoxy)-4-(2,4,4-trimethylpentan-2-yl)benzene Chemical compound CC(C)COC1=CC=C(C(C)(C)CC(C)(C)C)C=C1 YQHPSRBZZDBQKI-UHFFFAOYSA-N 0.000 description 1
HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
DBNQZGPCPCXGCX-UHFFFAOYSA-N 1-hydroxy-4-(4-nitrophenoxy)-2-naphthoic acid Chemical compound C=12C=CC=CC2=C(O)C(C(=O)O)=CC=1OC1=CC=C([N+]([O-])=O)C=C1 DBNQZGPCPCXGCX-UHFFFAOYSA-N 0.000 description 1
JBZCRFOFWKDWIO-UHFFFAOYSA-N 1-hydroxy-n-[2-(2-methylpropoxy)-5-(2,4,4-trimethylpentan-2-yl)phenyl]-4-(4-nitrophenoxy)naphthalene-2-carboxamide Chemical compound CC(C)COC1=CC=C(C(C)(C)CC(C)(C)C)C=C1NC(=O)C1=CC(OC=2C=CC(=CC=2)[N+]([O-])=O)=C(C=CC=C2)C2=C1O JBZCRFOFWKDWIO-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
SFKHDDRNYAGNFJ-UHFFFAOYSA-N 2-(2-methylpropoxy)-5-(2,4,4-trimethylpentan-2-yl)aniline Chemical compound CC(C)COC1=CC=C(C(C)(C)CC(C)(C)C)C=C1N SFKHDDRNYAGNFJ-UHFFFAOYSA-N 0.000 description 1
RLXVBFBDUXSRQW-UHFFFAOYSA-N 2-bromo-n-(2-methoxyethyl)acetamide Chemical compound COCCNC(=O)CBr RLXVBFBDUXSRQW-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
NZWIYPLSXWYKLH-UHFFFAOYSA-N 3-(bromomethyl)heptane Chemical compound CCCCC(CC)CBr NZWIYPLSXWYKLH-UHFFFAOYSA-N 0.000 description 1
XHXHIXJOWGRFEP-UHFFFAOYSA-N 4-(4-aminophenoxy)-1-hydroxy-n-[2-(2-methylpropoxy)-5-(2,4,4-trimethylpentan-2-yl)phenyl]naphthalene-2-carboxamide Chemical compound CC(C)COC1=CC=C(C(C)(C)CC(C)(C)C)C=C1NC(=O)C1=CC(OC=2C=CC(N)=CC=2)=C(C=CC=C2)C2=C1O XHXHIXJOWGRFEP-UHFFFAOYSA-N 0.000 description 1
ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
206010070834 Sensitisation Diseases 0.000 description 1
YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
125000005138 alkoxysulfonyl group Chemical group 0.000 description 1
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
XYXNTHIYBIDHGM-UHFFFAOYSA-N ammonium thiosulfate Chemical compound [NH4+].[NH4+].[O-]S([O-])(=O)=S XYXNTHIYBIDHGM-UHFFFAOYSA-N 0.000 description 1
229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
125000005199 aryl carbonyloxy group Chemical group 0.000 description 1
125000005162 aryl oxy carbonyl amino group Chemical group 0.000 description 1
125000005142 aryl oxy sulfonyl group Chemical group 0.000 description 1
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
229910001864 baryta Inorganic materials 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
230000008859 change Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000003975 dentin desensitizing agent Substances 0.000 description 1
KYQODXQIAJFKPH-UHFFFAOYSA-N diazanium;2-[2-[bis(carboxymethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [NH4+].[NH4+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O KYQODXQIAJFKPH-UHFFFAOYSA-N 0.000 description 1
229960001484 edetic acid Drugs 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012634 fragment Substances 0.000 description 1
230000006870 function Effects 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000031700 light absorption Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000006224 matting agent Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000005499 phosphonyl group Chemical group 0.000 description 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
230000001235 sensitizing effect Effects 0.000 description 1
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 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
- G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
- G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
- G03C7/30517—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution
- G03C7/30523—Phenols or naphtols couplers
- 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
- G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific
- 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
- G03C7/34—Couplers containing phenols
- G03C7/344—Naphtholic couplers

Definitions

This invention relates to a cyan dye-forming coupler and, more specifically, to a silver halide light-sensitive color photographic material, which contains a 1-naphthol-type cyan dye-forming coupler having in its second-position an orthoalkoxyphenylcarbamoyl group and fourth-position an aliphaticoxy group, an aryloxy group or a heterocyclicoxy group.
a color image is formed by imagewise exposing a silver halide light-sensitive color photographic material and undergoing color development in which a dye image is formed by the reaction of a dye-forming coupler with a paraphenylenediamine-type color developing agent.
phenol type and naphthol type compounds are representative and, among them, naphthol-type compounds are used in color negative films for their photographic characteristics showing sufficient light absorption in the long wavelength region and high coupling reactivity.
2-arylcarbamoyl-1-naphthol-type couplers disclosed in U.S. Patent No.3,488,193 have an advantage that color density is not tend to decrease when processed with a fatigued bleaching solution, however, they have disadvantages that the maximum absorption wavelength shifts to short wavelength side in high color density area and color reproduction property is poor.
2-arylcarbamoyl-1-naphthol type cyan couplers disclosed in Japanese Patent Publication No.62-837475(1987), have an advantage that the maximum absorption wavelength does not shift remarkably to short wavelength side, however, the cyan couplers have a disadvantage that, in conventional color nega type developing, the maximum absorption wavelength becomes often the wavelength of not less than 700nm.
a preferable wavelength range is within the range of 685nm to 700nm, so that the maximum wavelength is longer than the preferable wavelength and color reproduction is poor.
Japanese Patent Publication No.5-40891(1993) discloses naphthol-type compounds, in which the aryl group at 2-position is substituted by a branched alkoxyl group, whereby shift of the maximum absorption wavelength was unsatisfactorily improved, however, there was still a problem that fog increases when the light-sensitive color photographic material containing this type of coupler is stored before exposure under high temperature and high humidity conditions.
the first object of the present invention is to provide a silver halide color photographic light-sensitive material, which is capable of producing a dye image of enhanced sensitivity and improved image quality by employing a 1-naphthol-type cyan dye-forming coupler.
the second object of the present invention is to provide a silver halide color photographic light-sensitive material comprising a 1-naphthol-type cyan dye-forming coupler which is capable of forming a cyan dye image having a favorable spectral absorption property and, especially, having a favorable maximum absorption wavelength
the third object of the present invention is to provide a silver halide color photographic light-sensitive material which comprises a 1-naphthol-type cyan dye-forming coupler where the density loss of the cyan dye produced therefrom is reduced even when it is processed with a fatigued bleaching solution.
the fourth object of the present invention is to provide a silver halide light-sensitive color photographic material having improved storage stability before exposure.
R1 and R2 straight-chained, branched or cyclic alkyl group, an alkenyl group and an alkynyl group, which may have a substituent, can be mentioned.
the aliphatic group represented by R includes preferably, those having 4 to 20 carbon atom such as, for example, butyl group, iso-butyl group, pentyl group, neo-pentyl group, isopentyl group, hexyl group, cyclohexyl group, octyl group, 2-ethylhexyl group, decyl group, dodecyl group, 2-methyloctyl group, 2-butyloctyl group, 2-hexyldecyl group, 5,7-dimethyloctyl group, 3,5,5-trimethylhexyl group and hexadecyl group.
the aliphatic group represented by R2 includes preferably an alkyl group having 1-20 carbon atoms such as, for example, methyl group, ethyl group, propyl group, iso-propyl group and those mentioned concerning R1.
the total number of carbon atoms contained in R1 and R2 is 8 or more, and it is preferably to 10 to 32 and, more preferably, at least one of them is a branched alkyl group.
R3 represents a substituent including, for example, an aliphatic group, an aryl group, a halogen atom, a hydroxyl group, an amino group, a carbonamide group, a sulfonamido group, a ureido group, an acyloxy group, an aliphaticoxy group, an aliphatic thio group, an aryl thio group and a sulfamoylamino group.
aliphatic group represented by R in Formula 1 a straight-chained, branched or cyclic alkyl group having 1 to 30 carbon atoms and a substituted alkyl group are preferable and, a substituted alkyl group having 2 to 30 carbon atoms is more preferable.
substituted or unsubstituted phenyl or naphthyl group is preferable.
a substituted phenyl group having 6 to 30 carbon atoms is especially preferable.
substituent of the substituted phenyl group for example, those groups mentioned as the substituent for the substituted alkyl group for R can be mentioned.
a five-member or six-member heterocyclic ring containing therein at least one hetero atom selected from nitrogen, oxygen and sulfur, or a fused ring formed from the above-mentioned five-member or six-member heterocyclic ring and another aromatic ring or a heterocyclic ring is preferable, and these fused rings may be substituted by a proper substituent, such as those mentioned as the substituent for the substituted alkyl group represented by R.
R an aliphatic group or an aryl group is preferable.
compounds represented by Formula(l) especially preferable compound can be presented by Formula 3. wherein R4, R5, R6 and R7 independently represent a straight-chained or branched alkyl group, provided that the total number of carbon atoms contained in R4 through R6 is 6 through 28; R' represents a substituted alkyl group having 2 to 30 carbon atoms or a substituted phenyl group having 6 to 30 carbon atoms.
substituent for the substituted alkyl group or the substituted phenyl group represented by R' those groups mentioned as the examples of the substituent for the substituted alkyl group in the aliphatic group as R can be mentioned.
the aliphatic group represented by Q1 and Q2 is straight-chained , branched or cyclic alkyl, alkenyl or alkynyl group, and the aliphatic group may have a substituent.
an alkyl group having 4 to 20 carbon atoms is preferable, and the alkyl group preferable includes, for example, butyl group, iso-butyl group, pentyl group, neo-pentyl group, iso-pentyl group, hexyl group cyclohexyl group, octyl group, 2-ethylhexyl group, decyl group, dodecyl group ,2-methyloctyl group, 2-butyloctyl group, 2-hexyldecyl group, 5,7-di-methyloctyl group, 3,5,5-trimethylhexyl group and hexadecyl group.
an alkyl group having 2 to 20 carbon atoms is preferable and, more preferably, a branched or a cyclic alkyl group having 4 to 20 carbon atoms, including, for example, sec-butyl group, tert-butyl group, 1,1,3,3-tetramethylbutyl group, cyclopentyl group, cyclohexyl group, 1-ethyl-1-methylpropyl group, 1-ethyl-1-methylpentyl group, 1-hexyl-1-methylnonyl group, bicyclooctyl group, admantyl group.
the total number of carbon atoms contained in Q1 and Q2 is 8 or more, and it is preferably to 10 to 32.
Q3 represents a substituent
a substituent preferable includes, for example, an aliphatic group, an aryl group, a halogen atom, a hydroxyl group, an amino group, a carbonamide group, a sulfonamido group, a ureido group, an acyloxy group, an aliphatic oxy group, an aliphatic thio group, an aryl thio group and a sulfamoylamino group.
aliphatic group represented by Q in Formula 2 a straight-chained, branched or cyclicalkyl group having 1 to 30 carbon atoms and a substituted alkyl group are preferable and, especially, a substituted alkyl group having 2 to 30 carbon atoms is preferable.
substituted or unsubstituted phenyl or naphthyl group is preferable.
a substituted phenyl group having 6 to 30 carbon atoms is especially preferable.
substituent of the substituted phenyl group for example, those groups mentioned as the substituent for the substituted alkyl group for Q can be mentioned,
a five-member or six-member heterocyclic ring having therein at least one hetero atom selected from nitrogen, oxygen and sulfur, or a fused ring formed from the five-member or six-member heterocyclic ring and another aromatic ring or a heterocyclic ring is preferable, and these fused rings may be substituted by a substituent, such as those mentioned as the substituent for the substituted alkyl group represented by Q.
an aliphatic group or an aryl group is more preferable.
Q4 represents a straight-chain, branched or cyclicalkyl group such as those mentioned above as the examples of Q1
Q5 represents a tertiary alkyl group having 4 to 20 carbon atoms such as tert-butyl group, tert-amyl group, 1,1,3,3-tetramethylbutyl group, 1-ethyl-1-methylpentyl group, 1-hexyl-1-methylnonyl group, bicyclooctyl group and adamantyl group or a five member or six-member cyclicalkyl group such as cyclohexyl group
Q' represents a substituted alkyl group having 2 to 30 carbon atoms or a substituted phenyl group having 6 to 30 carbon atoms.
aryl group represented by R11 or R12 for example, a phenyl group and a naphthyl group can be mentioned.
Preferable number of the substituent is preferable to be 1 to 5, provided that when there are two or more of substituents, they may be either same or different.
Preferable substituent on R11 are a halogen atom, an alkylsulfonyl group and a cyano group.
R12 is one represented by Formula B; wherein, J represents an oxygen atom or a sulfur atom; k represents an integer of 0 to 4; 1 represents zero or one, provided that when k is two or more, the plural number of R14, may be either same or different; R13 represents an alkylene group, R14 represents a substituent.
substituent represented by R14 for example, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a hydroxy group, an acyloxy group, an alkylcarbonyloxy group, an arylcarbonyloxy group, a carboxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkylthio group, an acyl group, an acylamino group, a sulfonamido group, a carbamoyl group and a sulfamoyl group.
the elimination group represented X11 for example, a halogen atom, an aryloxy group, a carbamoyloxy group, a carbamoylmethoxy group, an acyloxy group, a sulfonamido group and a succinicimido group can be mentioned.
R21, R22 and R23 independently represent a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group and, among these groups, the alkyl group is preferable.
substituents mentioned above may have a substituent and such substituent includes, for example, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an acylamino group, a sulfonamido group, an alkylthio group, an arylthio group, a halogen atom, a heterocyclic group, a sulfonyl group, a sulfinyl group, a phosphonyl group, an acyl group, a carbamoyl group, a sulfamoyl group, a cyano group, an alkoxy group, an aryloxy group, a heterocyclicoxy group, a siloxy group, an acyloxy group, a carbamoylalkoxy group, an amino group, an alkylamino group an imido group, a ureido group, a sulfamoylamino group, an al
Compound I-1 can be synthesized according to the following scheme.
Compound I-2 can be synthesized according to the following scheme.
Compound II-6 can be synthesized according to the following scheme.
Compound II-10 is synthesized according to the following scheme.
the cyan dye-forming coupler represented by the above-mentioned Formula 1 or 2 is incorporated in at least one red-sensitive silver halide emulsion layer.
the cyan dye-forming couplers represented by the formulae 1 and 6 or formulas 2 and 6 can be used in the optional proportion, however, preferably, within a molar ratio of 1/1 to 1/10.
the cyan dye-forming couplers represented by the Formulae 1, 2 and 6 may be used in the quantity of 1x10 ⁇ 3 to 8x10 ⁇ 1 mol and, more preferably, 1x10 ⁇ to 8x10 ⁇ 1 mol per a mol of silver halide.
Amount of the compound represented by the Formula A-1 is preferably 0.01 to 10 g and, more preferably, 0.1 to 3.0 g per one gram of the cyan dye-forming coupler represented by Formulas 1, 2 or 6. Moreover the compound represented by the Formula A-1 may be used either one kind or two or more kinds in combination.
a high-speed rotary mixer such as a colloid mill or a ultra-sonic homogenizer
this may be incorporated into the emulsion, either directly or after it being is set, cut and washed with water.
the compound represented by Formulas 1, 2, 6 or A-1 may be incorporated in the silver halide emulsion layer either separately after separately dissolving in the high boiling-point solvent and dispersing in the above-mentioned method, or at a time. Furthermore, concerning the compounds represented by Formulas 1, 2, 6 or A-1 it is preferable that compounds are dissolved, and dispersed altogether and incorporated in the silver halide emulsion layer.
silver halide emulsion used in the light-sensitive material of the present invention any kind of silver halide emulsion which is known in the art can optionally be employed.
the emulsion may undergo a conventional chemical sensitization, and can be spectrally sensitized with a conventional sensitizing dye, to make the emulsion sensitive to any pre-designed spectral region.
the silver halide emulsion can comprise one or more kinds of photographic additives such as an anti-foggant, a stabilizer, etc.
photographic additives such as an anti-foggant, a stabilizer, etc.
the binder for the emulsion it is preferable to use gelatin.
the silver halide emulsion layer and other hydrophilic colloidal layer may be hardened and can comprise a plasticizer and a dispersion containing a polymer which is insoluble or sparsely soluble in water.
a coupler is used in the silver halide emulsion layer of the color photographic light-sensitive material.
a colored coupler having a function as a color compensator, a competing coupler, a compound which is, upon reaction with an oxidation product of a color developing agent capable of splitting off a photographically useful fragment such as a development accelerator, a bleach accelerator, a developing agent, a solvent for the silver halide, a color toning agent, a hardener, a fogging agent, an anti-foggant, a chemical sensitizer, a spectral sensitizer, a desensitizing agent.
the support for example, paper laminated with a polymer such as polyethylene, a polyethyleneterephthalate film, a baryta paper and a cellullose triacetate may be used.
a polymer such as polyethylene, a polyethyleneterephthalate film, a baryta paper and a cellullose triacetate
color photographic process which is generally known in the art may be applied.
the present invention can be applied to any type of silver halide light-sensitive materials known in the art, including negative-type color films, color papers and reversal-type color films.
the amount of addition of the additive in the silver halide light-sensitive photographic material is given, unless defined otherwise, in terms of weight (g) a square meter of the light-sensitive material. Concerning the amount of silver halide and colloidal silver, they are expressed in terms of equivalent amount of silver.
UV-1 UV Absorbent
CC-1 Colored coupler
CM-1 Colored coupler
Ole-1 High boiling-point solvent
Second Layer Intermediate Layer (IL-1)
UV absorbent 0.01
High boiling-point solvent Ole-1
Twelfth Layer Second Protective Layer (PRO-2)
Respective layers contain, in addition to those components mentioned above, a coating aid Su-2, a dispersion aid Su-3, gelatin hardeners H-1 and H-2, and anti foggants AF-1 and AF-2.
Silver halide emulsions used in this example are as follows.
Distribution of width(%) (standard deviation/average grain size) x 100
Ammonium ferric(III) ethylenediaminetetracetic acid 100 g Diammonium ethylenediaminetetracetic acid 10.0 g Ammonium bromide 150.0 g Acetic acid 10 ml
This solution has the same composition as "Bleach Solution A” except that 2.5 g of sodium hydrosulfite was added to a liter of the above-mentioned "Bleaching Solution A”.
maximum absorption means the maximum absorption wavelength(nm) of a sample at a portion of which density measured with red light is 1.0, when it is processed with "processing A”.
Density difference in Tables 1 and 2 represents numeral values of the 100-times-multiplied ratio of the maximum densities of the respective samples measured with red light between when it is processed with "processing A" and "Processing B".
the term "storage preservation property before exposure” represents density differences in the fog in the red-sensitive layer of the samples, one of which is placed under atomospheric conditions at 55°C and 65% R.H. for three days and, thereafter subjected to exposure and developing process with "Processing A” and another which does not undergo such experiment.
the samples containing the cyan dye-forming coupler according to the present invention have enhanced sensitivity, favorable maximum absorption wavelength, reduced density difference even when it is processed with a fatigue bleaching solution and improved storage preservation property before exposure.
Sample 2-1 was prepared in the same manner as in Sample 1 of Example 1, except for the following items 1 through 3.
Samples 2-2 through 2-5 were prepared in the same manner as in Sample 2-1, except that the coupler C-B employed in 3rd and 4th layers of Sample 1 was replaced with the same mols of the coupler shown in Table 3, respectively.
Comparative Sample 2-1 in which Comparative dye-forming coupler C-B and high boiling-point solvent Oil-1 are used, have good optical absorption, however, density change in the processing with the fatigue bleaching solution and fogging in the storage before exposure are large.

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Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Silver Salt Photography Or Processing Solution Therefor (AREA)

EP95304580A 1994-06-29 1995-06-29 Matériau photographique à couleurs à l'halogénure d'argent sensible à la lumière Withdrawn EP0690344A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP14808194A JPH0815833A (ja)	1994-06-29	1994-06-29	ハロゲン化銀カラー写真感光材料
JP148081/94		1994-06-29
JP22682394A JP3254455B2 (ja)	1994-09-21	1994-09-21	ハロゲン化銀カラー写真感光材料
JP226823/94		1994-09-21

Publications (1)

Publication Number	Publication Date
EP0690344A1 true EP0690344A1 (fr)	1996-01-03

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EP95304580A Withdrawn EP0690344A1 (fr)	1994-06-29	1995-06-29	Matériau photographique à couleurs à l'halogénure d'argent sensible à la lumière

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EP0730197A3 (fr) *	1995-02-28	1996-09-11	Konishiroku Photo Ind
US7351834B1 (en)	1999-01-13	2008-04-01	Bayer Pharmaceuticals Corporation	ω-Carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US7517880B2 (en)	1997-12-22	2009-04-14	Bayer Pharmaceuticals Corporation	Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas
US7838541B2 (en)	2002-02-11	2010-11-23	Bayer Healthcare, Llc	Aryl ureas with angiogenesis inhibiting activity
US7897623B2 (en)	1999-01-13	2011-03-01	Bayer Healthcare Llc	ω-carboxyl aryl substituted diphenyl ureas as p38 kinase inhibitors
US8076488B2 (en)	2003-02-28	2011-12-13	Bayer Healthcare Llc	Bicyclic urea derivatives useful in the treatment of cancer and other disorders
US8124630B2 (en)	1999-01-13	2012-02-28	Bayer Healthcare Llc	ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
WO2012142879A1 (fr)	2011-04-20	2012-10-26	佛山市优特医疗科技有限公司	Pansement ayant des propriétés bactériostatiques et hygroscopiques
US8637553B2 (en)	2003-07-23	2014-01-28	Bayer Healthcare Llc	Fluoro substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions
US8796250B2 (en)	2003-05-20	2014-08-05	Bayer Healthcare Llc	Diaryl ureas for diseases mediated by PDGFR

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JPS5965844A (ja)	1982-10-07	1984-04-14	Fuji Photo Film Co Ltd	ハロゲン化銀カラ−写真感光材料
JPS5971051A (ja)	1982-10-15	1984-04-21	Konishiroku Photo Ind Co Ltd	シアン色素画像形成方法
JPS5986048A (ja)	1982-11-09	1984-05-18	Fuji Photo Film Co Ltd	ハロゲン化銀カラ−写真感光材料
JPS59105644A (ja)	1982-12-10	1984-06-19	Konishiroku Photo Ind Co Ltd	ハロゲン化銀写真感光材料
JPS59111643A (ja)	1982-12-17	1984-06-27	Konishiroku Photo Ind Co Ltd	ハロゲン化銀写真感光材料
JPS59111644A (ja)	1982-12-17	1984-06-27	Konishiroku Photo Ind Co Ltd	ハロゲン化銀写真感光材料
JPS59131939A (ja)	1983-01-18	1984-07-28	Konishiroku Photo Ind Co Ltd	ハロゲン化銀写真感光材料
JPS59198455A (ja)	1983-04-26	1984-11-10	Fuji Photo Film Co Ltd	ハロゲン化銀カラ−写真感光材料
JPS6035731A (ja)	1983-08-08	1985-02-23	Fuji Photo Film Co Ltd	カラ−写真感光材料
JPS6037557A (ja)	1983-08-10	1985-02-26	Fuji Photo Film Co Ltd	カラ−写真感光材料
JPS6049335A (ja)	1983-08-29	1985-03-18	Fuji Photo Film Co Ltd	ハロゲン化銀カラ−写真感光材料
JPS6049336A (ja)	1983-08-29	1985-03-18	Fuji Photo Film Co Ltd	ハロゲン化銀カラ−写真感光材料
JPS6050533A (ja)	1983-08-30	1985-03-20	Fuji Photo Film Co Ltd	ハロゲン化銀カラ−写真感光材料
JPS6091355A (ja)	1983-10-25	1985-05-22	Fuji Photo Film Co Ltd	ハロゲン化銀カラ−写真感光材料
JPS60107650A (ja)	1983-11-16	1985-06-13	Konishiroku Photo Ind Co Ltd	ハロゲン化銀写真感光材料
JPS60107649A (ja)	1983-11-16	1985-06-13	Konishiroku Photo Ind Co Ltd	ハロゲン化銀写真感光材料
JPS612757A (ja)	1984-06-14	1986-01-08	Fuji Photo Film Co Ltd	２−アミノ−５−ニトロフエノ−ル誘導体の製造方法
JPS6237475A (ja)	1985-08-09	1987-02-18	トヨタ自動車株式会社	車両用キ−レスエントリ装置
JPH04125637A (ja) *	1990-09-18	1992-04-27	Fuji Photo Film Co Ltd	ハロゲン化銀カラー写真感光材料
JPH0540891A (ja)	1990-11-30	1993-02-19	Mitsubishi Electric Corp	負荷制御装置
US5302500A (en) *	1991-02-08	1994-04-12	Konica Corporation	Silver halide color photographic light-sensitive material offering excellent hue reproduction

1995
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US5728513A (en) *	1995-02-28	1998-03-17	Konica Corporation	Silver halide color photographic light sensitive material
EP0730197A3 (fr) *	1995-02-28	1996-09-11	Konishiroku Photo Ind
US7517880B2 (en)	1997-12-22	2009-04-14	Bayer Pharmaceuticals Corporation	Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas
US7351834B1 (en)	1999-01-13	2008-04-01	Bayer Pharmaceuticals Corporation	ω-Carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US7897623B2 (en)	1999-01-13	2011-03-01	Bayer Healthcare Llc	ω-carboxyl aryl substituted diphenyl ureas as p38 kinase inhibitors
US8124630B2 (en)	1999-01-13	2012-02-28	Bayer Healthcare Llc	ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US8841330B2 (en)	1999-01-13	2014-09-23	Bayer Healthcare Llc	Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US8618141B2 (en)	2002-02-11	2013-12-31	Bayer Healthcare Llc	Aryl ureas with angiogenesis inhibiting activity
US7838541B2 (en)	2002-02-11	2010-11-23	Bayer Healthcare, Llc	Aryl ureas with angiogenesis inhibiting activity
US8242147B2 (en)	2002-02-11	2012-08-14	Bayer Healthcare Llc	Aryl ureas with angiogenisis inhibiting activity
US8076488B2 (en)	2003-02-28	2011-12-13	Bayer Healthcare Llc	Bicyclic urea derivatives useful in the treatment of cancer and other disorders
US8796250B2 (en)	2003-05-20	2014-08-05	Bayer Healthcare Llc	Diaryl ureas for diseases mediated by PDGFR
US8637553B2 (en)	2003-07-23	2014-01-28	Bayer Healthcare Llc	Fluoro substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions
WO2012142879A1 (fr)	2011-04-20	2012-10-26	佛山市优特医疗科技有限公司	Pansement ayant des propriétés bactériostatiques et hygroscopiques

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US4228233A (en)	1980-10-14	Photographic silver halide light-sensitive material
EP0690344A1 (fr)	1996-01-03	Matériau photographique à couleurs à l'halogénure d'argent sensible à la lumière
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JPH01206338A (ja)	1989-08-18	ハロゲン化銀カラー写真感光材料
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DE3819051A1 (de)	1989-12-07	Farbfotografisches aufzeichnungsmaterial
US4120723A (en)	1978-10-17	Color photographic light-sensitive element
JPS59105644A (ja)	1984-06-19	ハロゲン化銀写真感光材料
US4191574A (en)	1980-03-04	Process for forming a photographic magenta dye image
JP3254455B2 (ja)	2002-02-04	ハロゲン化銀カラー写真感光材料
JPH0451236A (ja)	1992-02-19	ハロゲン化銀カラー写真感光材料
US4205990A (en)	1980-06-03	Process for forming a cyan dye image by the use of a 2-equivalent cyan coupler
JP3245762B2 (ja)	2002-01-15	ハロゲン化銀カラー写真感光材料
US5534400A (en)	1996-07-09	Silver halide color photographic light-sensitive material
JP2909937B2 (ja)	1999-06-23	ハロゲン化銀カラー写真感光材料
EP0686871A1 (fr)	1995-12-13	Matériau photographique couleur à l'halogénure d'argent sensible à la lumière
JPH1195381A (ja)	1999-04-09	シアンカプラー及びこれを含有するハロゲン化銀カラー写真感光材料
JPH08211578A (ja)	1996-08-20	ハロゲン化銀カラー写真感光材料
EP0422505A1 (fr)	1991-04-17	Matériau photographique couleur à l'halogénure d'argent sensible à la lumière
JPH04238347A (ja)	1992-08-26	ハロゲン化銀カラー写真感光材料

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