JPS6232780B2 - - Google Patents
Info
- Publication number
- JPS6232780B2 JPS6232780B2 JP16316779A JP16316779A JPS6232780B2 JP S6232780 B2 JPS6232780 B2 JP S6232780B2 JP 16316779 A JP16316779 A JP 16316779A JP 16316779 A JP16316779 A JP 16316779A JP S6232780 B2 JPS6232780 B2 JP S6232780B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- coupler
- pat
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000839 emulsion Substances 0.000 claims description 29
- 239000000463 material Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000000654 additive Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 239000000084 colloidal system Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 125000004442 acylamino group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- NDGRWYRVNANFNB-UHFFFAOYSA-N pyrazolidin-3-one Chemical class O=C1CCNN1 NDGRWYRVNANFNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- 238000009792 diffusion process Methods 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 claims 1
- -1 silver halide Chemical class 0.000 description 65
- 239000000975 dye Substances 0.000 description 40
- 239000010410 layer Substances 0.000 description 27
- 238000000034 method Methods 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 230000035945 sensitivity Effects 0.000 description 16
- 108010010803 Gelatin Proteins 0.000 description 14
- 229920000159 gelatin Polymers 0.000 description 14
- 239000008273 gelatin Substances 0.000 description 14
- 235000019322 gelatine Nutrition 0.000 description 14
- 235000011852 gelatine desserts Nutrition 0.000 description 14
- 229910052709 silver Inorganic materials 0.000 description 14
- 239000004332 silver Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical class N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 description 12
- 125000004414 alkyl thio group Chemical group 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 10
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 8
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 125000005110 aryl thio group Chemical group 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 239000007844 bleaching agent Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000001235 sensitizing effect Effects 0.000 description 5
- 235000010265 sodium sulphite Nutrition 0.000 description 5
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 238000004061 bleaching Methods 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical group NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 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 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- XYXNTHIYBIDHGM-UHFFFAOYSA-N ammonium thiosulfate Chemical compound [NH4+].[NH4+].[O-]S([O-])(=O)=S XYXNTHIYBIDHGM-UHFFFAOYSA-N 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
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 2
- 150000001661 cadmium Chemical class 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 238000005859 coupling reaction Methods 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
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical class OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 1
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical class C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- ODIRBFFBCSTPTO-UHFFFAOYSA-N 1,3-selenazole Chemical class C1=C[se]C=N1 ODIRBFFBCSTPTO-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- YGDWUQFZMXWDKE-UHFFFAOYSA-N 1-oxido-1,3-thiazole Chemical class [O-]S1=CN=C=C1 YGDWUQFZMXWDKE-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- KPVMVJXYXFUVLR-UHFFFAOYSA-N 12-ethyltetradecan-1-amine Chemical compound CCC(CC)CCCCCCCCCCCN KPVMVJXYXFUVLR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- HXJQNHSMRSFUMA-UHFFFAOYSA-N 2,3-dimethyl-5-(2,4,4-trimethylpentan-2-yl)benzene-1,4-diol Chemical compound CC1=C(C)C(O)=C(C(C)(C)CC(C)(C)C)C=C1O HXJQNHSMRSFUMA-UHFFFAOYSA-N 0.000 description 1
- 150000001473 2,4-thiazolidinediones Chemical class 0.000 description 1
- CLDZVCMRASJQFO-UHFFFAOYSA-N 2,5-bis(2,4,4-trimethylpentan-2-yl)benzene-1,4-diol Chemical compound CC(C)(C)CC(C)(C)C1=CC(O)=C(C(C)(C)CC(C)(C)C)C=C1O CLDZVCMRASJQFO-UHFFFAOYSA-N 0.000 description 1
- ZHUWKKIRCLKYNJ-UHFFFAOYSA-N 2,5-bis(2-methylpentan-2-yl)benzene-1,4-diol Chemical compound CCCC(C)(C)C1=CC(O)=C(C(C)(C)CCC)C=C1O ZHUWKKIRCLKYNJ-UHFFFAOYSA-N 0.000 description 1
- ZZPZYXCZSXGABS-UHFFFAOYSA-N 2,5-bis(4-methoxyphenyl)benzene-1,4-diol Chemical compound C1=CC(OC)=CC=C1C1=CC(O)=C(C=2C=CC(OC)=CC=2)C=C1O ZZPZYXCZSXGABS-UHFFFAOYSA-N 0.000 description 1
- LDVHGNMWLOPCDT-UHFFFAOYSA-N 2,5-dichloro-3,6-diphenylbenzene-1,4-diol Chemical compound OC1=C(Cl)C(C=2C=CC=CC=2)=C(O)C(Cl)=C1C1=CC=CC=C1 LDVHGNMWLOPCDT-UHFFFAOYSA-N 0.000 description 1
- QVLXDGDLLZYJAM-UHFFFAOYSA-N 2,5-dioctylbenzene-1,4-diol Chemical compound CCCCCCCCC1=CC(O)=C(CCCCCCCC)C=C1O QVLXDGDLLZYJAM-UHFFFAOYSA-N 0.000 description 1
- VQZAODGXOYGXRQ-UHFFFAOYSA-N 2,6-didodecylbenzene-1,4-diol Chemical compound CCCCCCCCCCCCC1=CC(O)=CC(CCCCCCCCCCCC)=C1O VQZAODGXOYGXRQ-UHFFFAOYSA-N 0.000 description 1
- RDMIJQCFPQDYQN-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)benzene-1,4-diol Chemical compound CC(C)(C)CC(C)(C)C1=CC(O)=CC=C1O RDMIJQCFPQDYQN-UHFFFAOYSA-N 0.000 description 1
- BIEFDNUEROKZRA-UHFFFAOYSA-N 2-(2-phenylethenyl)aniline Chemical group NC1=CC=CC=C1C=CC1=CC=CC=C1 BIEFDNUEROKZRA-UHFFFAOYSA-N 0.000 description 1
- YFVJCMFQEOHVMO-UHFFFAOYSA-N 2-(3-pentadecylphenoxy)butanamide Chemical group CCCCCCCCCCCCCCCC1=CC=CC(OC(CC)C(N)=O)=C1 YFVJCMFQEOHVMO-UHFFFAOYSA-N 0.000 description 1
- QTLHLXYADXCVCF-UHFFFAOYSA-N 2-(4-amino-n-ethyl-3-methylanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(N)C(C)=C1 QTLHLXYADXCVCF-UHFFFAOYSA-N 0.000 description 1
- WFXLRLQSHRNHCE-UHFFFAOYSA-N 2-(4-amino-n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(N)C=C1 WFXLRLQSHRNHCE-UHFFFAOYSA-N 0.000 description 1
- WVYWKJADSZLVFW-UHFFFAOYSA-N 2-[(2,5-dihydroxybenzoyl)amino]ethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCNC(=O)C1=CC(O)=CC=C1O WVYWKJADSZLVFW-UHFFFAOYSA-N 0.000 description 1
- KCZVLCXXYXIDDK-UHFFFAOYSA-N 2-[2,4-bis(2-methylbutan-2-yl)phenoxy]butanamide Chemical group CCC(C(N)=O)OC1=CC=C(C(C)(C)CC)C=C1C(C)(C)CC KCZVLCXXYXIDDK-UHFFFAOYSA-N 0.000 description 1
- LOIUBRXCXMKWFZ-UHFFFAOYSA-J 2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;iron(4+) Chemical compound [Fe+4].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O LOIUBRXCXMKWFZ-UHFFFAOYSA-J 0.000 description 1
- BDOYKFSQFYNPKF-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid;sodium Chemical compound [Na].[Na].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O BDOYKFSQFYNPKF-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
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- RPLZABPTIRAIOB-UHFFFAOYSA-N 2-chloro-5-dodecylbenzene-1,4-diol Chemical compound CCCCCCCCCCCCC1=CC(O)=C(Cl)C=C1O RPLZABPTIRAIOB-UHFFFAOYSA-N 0.000 description 1
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- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002960 margaryl 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])C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QEALYLRSRQDCRA-UHFFFAOYSA-N myristamide Chemical group CCCCCCCCCCCCCC(N)=O QEALYLRSRQDCRA-UHFFFAOYSA-N 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- REMLBIQDWYHALC-UHFFFAOYSA-N n-[2-(4-amino-n-ethylanilino)ethyl]methanesulfonamide;sulfuric acid Chemical compound OS(O)(=O)=O.CS(=O)(=O)NCCN(CC)C1=CC=C(N)C=C1 REMLBIQDWYHALC-UHFFFAOYSA-N 0.000 description 1
- GOQNHVBVNGVLDV-UHFFFAOYSA-N n-[4-[2-(2,5-dihydroxyphenyl)ethyl]phenyl]octanamide Chemical compound C1=CC(NC(=O)CCCCCCC)=CC=C1CCC1=CC(O)=CC=C1O GOQNHVBVNGVLDV-UHFFFAOYSA-N 0.000 description 1
- KWGCJVWBEVNKIA-UHFFFAOYSA-N n-dodecyl-2,5-dihydroxybenzamide Chemical compound CCCCCCCCCCCCNC(=O)C1=CC(O)=CC=C1O KWGCJVWBEVNKIA-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- VECVSKFWRQYTAL-UHFFFAOYSA-N octyl benzoate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1 VECVSKFWRQYTAL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000006179 pH buffering agent Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003236 pyrrolines Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 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 class O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 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
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- UWSAIOMORQUEHN-UHFFFAOYSA-L sodium;2-[2-[carboxylatomethyl(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetate;iron(5+) Chemical compound [Na+].[Fe+5].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O UWSAIOMORQUEHN-UHFFFAOYSA-L 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 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
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KSYNLCYTMRMCGG-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;dihydrate Chemical compound O.O.[Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O KSYNLCYTMRMCGG-UHFFFAOYSA-J 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000003475 thallium Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- NJPOTNJJCSJJPJ-UHFFFAOYSA-N tributyl benzene-1,3,5-tricarboxylate Chemical compound CCCCOC(=O)C1=CC(C(=O)OCCCC)=CC(C(=O)OCCCC)=C1 NJPOTNJJCSJJPJ-UHFFFAOYSA-N 0.000 description 1
- 150000003639 trimesic acids Chemical class 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/36—Couplers containing compounds with active methylene groups
- G03C7/38—Couplers containing compounds with active methylene groups in rings
- G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
本発明はカラー写真感光材料に関するもので、
とくに発色現像工程において色素形成収率が高
く、感度増加が得られるカラー写真感材に感する
ものである。
ハロゲン化銀カラー写真材料を発色現像するこ
とにより、酸化された芳香族一級アミン系カラー
現像主薬とカプラーとが反応してインドフエノー
ル、インドアニリン、インダミン、アゾメチン、
フエノキサジン、フエナジン及びそれに類する色
素ができ、色画像が形成されることは知られてい
る。この方式においては通常色再現には減色法が
使われ青、緑、および赤に選択的に感光するハロ
ゲン化銀乳剤と、それぞれ余色関係にあるイエロ
ー、マゼンタ、およびシアンの色画像形成剤とが
使用される。イエロー色画像を形成するために
は、例えばアシルアセトアニリド、又は、ジベン
ゾイルメタン系カプラーが使われ、マゼンタ色画
像を形成するためには、主としてピラゾロン、ピ
ラゾロベンツイミダゾール、シアノアセトフエノ
ンまたはイミダゾロン系カプラーが使われ、シア
ン色画像を形成するためには主としてフエノール
系カプラー、例えばフエノール類、及びナフトー
ル類が使われる。
従来の色画像を形成するカプラーは、その殆ん
どが4当量カプラーである。すなわちカツプリン
グ反応して1モルの色素を形成するのに、理論的
には酸化剤として4モルのハロゲン化銀の現像を
必要とする。これに対して芳香族一級アミン現像
薬の酸化生成物と酸化カツプリングして離脱する
基で置換された活性メチレン基を有する2当量カ
プラーは、1モルの色素を形成するために2モル
のハロゲン化銀の現像を必要とするのみである。
2当量カプラーでは色素を形成する際に必要なハ
ロゲン化銀の量が4当量カプラーの場合の二分の
一しか必要でないため、感光層の薄層化による感
光材料の迅速処理化、膜厚低減による写真性の向
上、ならびに経済性等の点で多くの効用が認めら
れる。
従来マゼンタ形成カプラーとして、主として使
用されてきた5−ピラゾロン型カプラーを2当量
化するいくつかの試みが提案されている。例え
ば、米国特許3214437号、および同3253924号には
ピラゾロンの4位をチオシアノ基によつて、米国
特許3311476号にはアシルオキシ基によつて、米
国特許3419391号にはアリールオキシ基によつ
て、米国特許3617291号には2−トリアゾリル基
によつて、米国特許3522052号にはハロゲン原子
によつて夫々置換することが記載されている。
しかしながら、これらの4位置換ピラゾロンカ
プラーを用いた場合には著しい色カブリの発生を
ひき起したり、反応活性が適当でなかつたり、カ
プラーが化学的に不安定であつて経時によつて発
色できない物質に変化したり、さらには合成上の
困難が多いなどのいずれかの不都合を伴うもので
あつた。
また以前より、米国特許3227554号に公示され
ているように5−ピラゾロンの4位を、アルキル
チオ基、アリールチオ基またはヘテロ環チオ基に
よつて置換することも知られていた。しかし、こ
れら公知のチオ置換ピラゾロン化合物の多くで
は、芳香族1級アミンカラー現像薬の酸化生成物
との反応活性が不適当であり、さらにカツプリン
グ反応の結果、生成するメルカプト化合物の強い
写真作用のために、一般のカラー感光材料への応
用には難があり、カプラーの化学的安定性も充分
ではなかつた。
又、最近のカラー感光材料の高感化という技術
的課題に対しては、前記の2当量マゼンタカプラ
ーの発色感度は必ずしも充分なものとはいえず、
マゼンタ色画像形成層の感度上昇の技術の開発が
強く望まれていた。
最近、アルキルチオ離脱基を有するマゼンタカ
プラーが特に活性が高く、発色感度も高いという
知見が得られたが(特願昭53−136497号参照)、
これでもまだ高感度のカラー感光材料を得るため
には不充分なものであり、これを更に改良するた
めこのマゼンタカプラーと1−フエニル−3−ピ
ラゾリドン誘導体との併用の技術が考えられ、一
段と高感度な感光材料を得ることが可能となつ
た。またこれによりアルキルチオ離脱基を有する
5−ピラゾロンカプラーの保存性も改良された。
しかしこの併用技術にはかぶりの上昇という副作
用が発生し、これを解決することは上記の併用技
術を実用化する上で必須のことであつた。
本発明の目的は第1にマゼンタ色画像形成層の
発色感度が高く、塗布銀量の少なく、且つかぶり
の低いカラー感光材料を提供することであり、第
2にかぶりを上昇させることなくアルキルチオ離
脱マゼンタカプラーを使用した感光材料の保存性
を改良することであり、第3にアルキルチオ離脱
マゼンタカプラーより生成する色素の耐光性、堅
牢性を改良することである。
本願の一般式()で表わされるカプラーと拡
散性の1−フエニル−3−ピラゾリドン誘導体と
だけの併用、および耐拡散性の1−フエニル−3
−ピラゾリドン誘導体をメタノール等の低沸点有
機溶媒に溶解して乳剤中に添加する方法では上記
目的は達成されない。
本発明の目的は、下記一般式()で表わされ
るカプラーを少なくとも1種含有する乳剤層中及
び/又は該乳剤層に隣接する親水性コロイド層中
に耐拡散性基を有する1−フエニル−3−ピラゾ
リドン誘導体及び一般式()で表わされるハイ
ドロキノン誘導体を、写真用添加剤用高沸点有機
溶媒の存在下で含有させることによつて達成され
る。
一般式()で表わされるカプラーと耐拡散性
油溶性1−フエニル−3−ピラゾリドン誘導体と
を混合して写真用添加剤用高沸点有機溶媒に溶解
して乳剤層中に分散させることは本発明の効果が
大きい点で特に好ましい。
一般式()で表わされるカプラー、本願1−
フエニル−3−ピラゾリドン誘導体及び一般式
()で表わされるハイドロキノン誘導体を三者
混合して高沸点有機溶媒に溶解して乳剤層中に分
散させることは本発明の効果がより一層大きくさ
らに好ましい。
一般式()
式中、R1はアニリノ基、アミルアミノ基又は
ウレイド基を表わし、R2はアラルキル基、炭素
数1〜22のアルキル基又はアルケニル基を表わ
し、X1、X2、X3は水素原子、アルキル基、ハロ
ゲン原子、アルコキシ基、アリールオキシ基、ア
シルアミノ基、カルバモイル基、スルフアモイル
基、スルホニル基又はシアノ基を表わし、X1、
X2、X3は同一の基であつても異なる基であつて
もよい。
さらに詳しくは、R1はアニリノ基(例えば、
フエニルアミノ基、o−クロロフエニルアミノ
基、2・4−ジクロロフエニルアミノ基、2・4
−ジクロロ−5−メトキシフエニルアミノ基、2
−クロロ−5−テトラデカンアミドフエニルアミ
ノ基、2−クロロ−5−{α−(2・4−ジ−t−
アミルフエノキシ)ブチルアミド}フエニルアミ
ノ基、2−クロロ−5−{(3−オクタデセニル)
サクシンイミド}フエニルアミノ基、2−クロロ
−5−〔α−{(3−t−ブチル−4−ヒドロキ
シ)フエノキシ}テトラデカンアミド〕フエニル
アミノ基など)、アシルアミノ基(例えば、アセ
チルアミノ基、ブチルアミド基、α−(3−ペン
タデシルフエノキシ)ブチルアミド基、n−テト
ラデカンアミド基、α−(2・4−ジ−t−アミ
ルフエノキシ)ブチルアミド基、3−{α−(2・
4−ジ−t−アミルフエノキシ)ブチルアミド}
ベンズアミド基、ベンズアミド基、3−アセチル
アミドベンズアミド基など)、ウレイド基(例え
ばフエニルウレイド基、メチルウレイド、3−
{α−(2・4−ジ−tert−アミルフエノキシ)ブ
チルアミド}フエニルウレイド、など)を表わ
し、X1、X2、X3は水素原子、アルキル基(例え
ば、メチル基、エチル基など)、ハロゲン原子
(クロル原子、ブロム原子、フツ素原子)、アルコ
キシ基(メトキシ基、エトキシ基、など)、アリ
ールオキシ基(例えば、フエニルオキシ基、ナフ
チルオキシ基、など)、アシルアミノ基(例え
ば、アセチルアミノ基、α−(2・4−ジ−t−
アミルフエノキシ)ブチルアミド基、など)、カ
ルバモイル基(例えば、メチルカルバモイル、フ
エニルカルバモイル基など)、スルフアモイル基
(例えば、メチルスルフアモイル基、フエニルス
ルフアモイル基など)、スルホニル基(例えば、
エチルスルホニル、ブチルスルホニル、メチルス
ルホニル基など)、シアノ基を表わす。R2は炭素
数1〜22の直鎖又は分岐鎖アルキル基を表わし、
置換されていてもよい。置換アルキル基の例は、
メチル基、エチル基、プロピル基、ブチル基、オ
クチル基、ドデシル基、テトラデシル基、オクタ
デシル基、又はヘプタデシル基である。分岐アル
キル基の例はi−プロピル基、tert−ブチル基で
ある。さらにR2はアラルキル基(例えば、ベン
ジル基、2−フエニルエチル基)又はアルケニル
基(例えば、プロペニル基)をあらわす。これら
のアルキル基、アラルキル基及びアルケニル基は
各々ハロゲン原子、ニトロ、シアノ、アリール、
アルコキシ、アリールオキシ、カルボキシ、アル
キルカルボニル、アリールカルボニル、アルコキ
シカルボニル、アリールオキシカルボニル、アシ
ルオキシ、スルフアモイル、カルバモイル、アシ
ルアミノ、ジアシルアミノ、ウレイド、チオウレ
イド、ウレタン、チオウレタン、スルホンアミ
ド、複素環、アリールスルホニルオキシ、アルキ
ルスルホニルオキシ、アリールスルホニル、アル
キルスルホニル、アリールチオ、アルキルチオ、
アルキルスルフイニル、アリールスルフイニル、
アルキルアミノ、ジアルキルアミノ、アニリノ、
N−アリールアニリノ、N−アルキルアニリノ、
N−アシルアニリノ及びヒドロキシ基から選ばれ
た置換基で置換されていてもよい。
一般式()で表わされるもののうちR2が炭
素数1〜5のアルキル基であるようなカプラーは
生成した色素の堅牢性が高いという点で特に好ま
しい。
一般式()で表されるカプラーの具体例にお
ける物性及び製法については特願昭53−136497
(特開昭55−62454号公報)に記載されている。
本発明の一般式()は以下の通りである。
一般式()
Rは炭素数8〜30のアルキル基、アリール基ア
ルコキシ基、アリールオキシ基、カルバモイル
基、スルフアモイル基、アルコキシカルボニル基
又はアリールオキシカルボニル基を表わす。以上
のうちのアルキル基及びアリール基はハロゲン原
子、アルキル基、アリール基、アルコキシ基、ア
リールオキシ基、カルボキシ基、アルコキシカル
ボニル基、アリールオキシカルボニル基、アシル
基、アシルオキシ基、カルバモイル基、スルホ
基、スルフアモイル基、スルホンアミド基、N−
アルキルアミノ基、N−アリールアミノ基、アシ
ルアミノ基、イミド基、ヒドロキシル基などの置
換基を持つていてもよい。
nは1〜4の数を表わし、nが2以上のとき、
各々のRは同じでも異なつていてもよい。
一般式()で表わされる化合物の具体例は以
下の通りである。
HQ−1 2・5−ジ−tert−オクチルハイドロ
キノン
HQ−2 2−tert−オクチル−5−メチルハイ
ドロキノン
HQ−3 2・6−ジ−n−ドデシル−ハイドロ
キノン
HQ−4 2−n−ドデシルハイドロキノン
HQ−5 2・2′−メチレンビス−5・5′−ジ−
tert−ブチルハイドロキノン
HQ−6 2・5−ジ−n−オクチルハイドロキ
ノン
HQ−7 2−ドデシルカルバモイルハイドロキ
ノン
HQ−8 2−(β−n−ドデシルオキシカルボ
ニル)エチルハイドロキノン
HQ−9 2−(N・N−ジブチルカルバモイ
ル)ハイドロキノン
HQ−10 2−n−ドデシル−5−クロロハイド
ロキノン
HQ−11 2−(2−オクタデシル)−5−メチル
ハイドロキノン
HQ−12 2・5−ジ−(p−メトキシフエニ
ル)ハイドロキノン
HQ−13 2−tert−オクチルハイドロキノン
HQ−14 2−〔β−{3−(3−スルホベンズア
ミド)ベンズアミド}エチルハイドロキ
ノン
HQ−15 2・5−ジクロロ−3・6−ジフエニ
ルハイドロキノン
HQ−16 2・6−ジメチル−3−tert−オクチ
ルハイドロキノン
HQ−17 2・3−ジメチル−5−tert−オクチ
ルハイドロキノン
HQ−18 2−{β−(ドデカノイルオキシ)エチ
ル}カルバモイルハイドロキノン
HQ−19 2−ドデシルオキシカルボニルハイド
ロキノン
HQ−20 2−{β−(4−オクタンアミドフエニ
ル)エチル}ハイドロキノン
HQ−21 2−メチル−5−ドデシルハイドロキ
ノン
HQ−22 2・5−ジ−tert−ヘキシルハイドロ
キノン
本発明に使用される1−フエニル−3−ピラゾ
リドン誘導体は単独であるいは2種以上を混合し
て使用できる。その添加量は2当量マゼンタカプ
ラー1モルに対して0.005モル〜10モル、好まし
くは0.01モルから2モルが好ましい。
本発明の1−フエニル−3−ピラゾリドン誘導
体は一般式()で表わされるものを包含する。
一般式()
式中R3は置換されていてもよいアリール基を
表わし、置換基としてはハロゲン原子、アルキル
基、アリール基、アラルキル基、アルコキシ基、
アリーロキシ基、アルキルチオ基、アリールチオ
基、アシルアミノ基、ニトロ基、スルホンアミノ
基、シアノ基、水酸基、スルホ基、カルボキシル
基又は、アルキルオキシカルボニル基があり、特
に好ましいものは、アルコキシ基、アリーロキシ
基、アルキルチオ基及びアリールチオ基である。
R4〜R7は各々水素原子、アルキル基、置換アル
キル基、(置換基としてはアリール基、水酸基、
ハロゲン原子、アシルオキシ基、アルキルオキシ
基、アリールオキシ基、アルキルチオ基、アリー
ルチオ基、ヘテロ環基)アリール基、置換アリー
ル基(置換基としてはアルキル基、アリール基、
ハロゲン原子、アルキルオキシ基、アリールオキ
シ基、アルキルチオ基、アリールチオ基、アミノ
基、アルキルアミノ基、アシルアミノ基、スルホ
ンアミノ基、シアノ基、ニトロ基、水酸基)、ア
ルキルオキシ基、アリールオキシ基又はアラルキ
ルオキシ基を表わす。
ただしR4〜R7のそれぞれの炭素数が6以下で
ある場合R3のアリール基は炭素数6以上である
置換基をもち、R3は炭素数6以下の置換基をも
つアリール基の場合R4〜R7のうちの少なくとも
1つは炭素数6以上である。
本発明に使用される写真添加剤用高沸点有機溶
媒は公知のものならなんでもよいが、例えば米国
特許2322027号に記載のフタール酸アルキルエス
テル(ジブチルフタレート、ジオクチルフタレー
トなど)、リン酸エステル(ジフエニルフオスフ
エート、トリフエニルフオスフエート、トリクレ
ジルフオスフエート、ジオクチルブチルフオスフ
エート)、クエン酸エステル(たとえばアセチル
クエン酸トリブチル)、安息香酸エステル(たと
えば安息香酸オクチル)、アルキルアミド(たと
えばジエチルラウリルアミド)、脂肪酸エステル
類(たとえばジブトキシエチルサクシネート、ジ
オクチルアゼレート)、トリメシン酸エステル類
(たとえばトリメシン酸トリブチル)などが好ま
しく、例えば米国特許2322027号、同2533514号、
同2835579号、特公昭46−23233号、米国特許
3287134号、英国特許958441号、特開昭47−
1031、英国特許1222753号、米国特許3936303号、
特開昭51−26037号、特開昭50−82078号、米国特
許2353262、同285238号、同3554755号、同
3676137号、同3676142号、同3700454号、同
3748141号、同3837863号、OLS2538889号、特開
昭51−27921号、同51−27922号、同51−26035
号、同51−26036号、同50−62632号、特開昭49−
29461号、米国特許3936303号、同3748141号、特
開昭53−1521号などに記載のものも好ましい。カ
プラーや1−フエニル−3−ピラゾリドン誘導体
を親水性コロイド層を導入するには前記の高沸点
有機溶媒を用いて米国特許2322027号に記載の方
法を用いたり、または沸点約30℃乃至150℃の有
機溶媒、たとえば酢酸エチル、酢酸ブチルのごと
き低級アルキルアセテート、フロピオン酸エチ
ル、2級ブチルアルコール、メチルイソブチルケ
トン、β−エトキシエチルアセテート、メチルセ
ロソルブアセテート等に溶解したのち、親水性コ
ロイドに分散される。上記の高沸点有機溶媒と低
沸点有機溶媒とを混合して用いてもよい。
また特公昭51−39853、特開昭51−59943に記載
されている重合物による分散法も使用することが
できる。
カプラーがカルボン酸、スルフオン酸のごとき
酸基を有する場合には、アルカリ性水溶液として
親水性コロイド中に導入される。
本発明の類似の技術が特開昭54−130928号に開
示されている。しかし該技術は5−ピラゾロンマ
ゼンタカプラーでなく、環の5位がオキソ基でな
く、スルホニルオキシ基又はカルボニルオキシ基
で置換されているピラゾールマゼンタカプラーに
ついてのものであり、実施例のデータから明らか
なごとくこのカプラーでは本発明の一般式()
の化合物と併用しても発色感度上昇効果がほとん
どないという点で本発明とは明らかに区別され、
又このような効果の差があることは真に予想外の
ことである。
本発明に用いられる写真乳剤はP.Glafkides著
Chimie et Physique Photographique(Paul
Montel社刊、1967年)、G.F.Duffin著
Photographic Emulsion Chemistry(The Focal
Press刊、1966年)、V.L.Zelikman et al著
Making and Coating Photographic Emulsion
(The Focal Press刊、1964年)などに記載され
た方法を用いて調製することができる。すなわ
ち、酸性法、中性法、アンモニア法等のいずれで
もよく、また可溶性銀塩と可溶性ハロゲン塩を反
応させる形式としては片側混合法、同時混合法、
それらの組合せなどのいずれを用いてもよい。
粒子を銀イオン過剰の下において形成させる方
法(いわゆる逆混合法)を用いることもできる。
同時混合法の一つの形式としてハロゲン化銀の生
成される液相中のpAgを一定に保つ方法、すなわ
ちいわゆるコントロールド・ダブルジエツト法を
用いることもできる。
この方法によると、結晶形が規則的で粒子サイ
ズが均一に近いハロゲン化銀乳剤がえられる。
別々に形成した2種以上のハロゲン化銀乳剤を
混合して用いてもよい。
ハロゲン化銀粒子形成または物理熟成の過程に
おいて、カドミウム塩、亜鉛塩、鉛塩、タリウム
塩、イリジウム塩またはその錯塩、ロジウム塩ま
たはその錯塩、鉄塩または鉄錯塩などを共存させ
てもよい。
本発明に用いられる写真乳剤は、メチン色素類
その他によつて分光増感されてよい。用いられる
色素には、シアニン色素、メロシアニン色素、複
合シアニン色素、複合メロシアニン色素、ホロポ
ーラーシアニン色素、ヘミシアニン色素、スチリ
ル色素、およびヘミオキソノール色素が包含され
る。特に有用な色素はシアニン色素、メロシアニ
ン色素および複合メロシアニン色素に属する色素
である。これらの色素数には塩基性異節環核とし
てシアニン色素類に通常利用される核のいずれを
も適用できる。すなわち、ピロリン核、オキサゾ
リン核、チアゾリン核、ピロール核、オキサゾー
ル核、チアゾール核、セレナゾール核、イミダゾ
ール核、テトラゾール核、ピリジン核など;これ
らの核に脂環式炭化水素環が融合した核;および
これらの核に芳香族炭化水素環が融合した核、す
なわち、インドレニン核、ベンズインドレニン
核、インドール核、ベンズオキサゾール核、ナフ
トオキサゾール核、ベンゾチアゾール核、ナフト
チアゾール核、ベンゾセレナゾール核、ベンズイ
ミダゾール核、キノリン核などが適用できる。こ
れらの核は炭素原子上に置換されていてもよい。
メロシアニン色素または複合メロシアニン色素
にはケトメチレン構造を有する核として、ピラゾ
リン−5−オン核、チオヒダントイン核、2−チ
オオキサゾリジン−2・4−ジオン核、チアゾリ
ジン−2・4−ジオン核、ローダニン核、チオバ
ルビツール酸核などの5〜6員異節環核を適用す
ることができる。
有用な増感色素は例えばドイツ特許929080号、
米国特許2231658号、同2493748号、同2503776
号、同2519001号、同2912329号、同3656959号、
同3672897号、同3694217号、同4025349号、同
4046572号、英国特許1242588号、特公昭44−
14030号、同52−24844に記載されたものである。
これらの増感色素は単独に用いてもよいが、そ
れらの組合せを用いてもよく、増感色素の組合せ
は特に強色増感の目的でしばしば用いられる。そ
の代表例は米国特許2688545号、同2977229号、同
3397060号、同3522052号、同3527641号、同
3617293号、同3628964号、同3666480号、同
3672898号、同3679428号、同3703377号、同
3769301号、同3814609号、同3837862号、同
4026707号、英国特許1344281号、同1507803号、
特公昭43−4936号、同53−12375号、特開昭52−
110618号、同52−109925号に記載されている。
増感色素とともに、それ自身分光増感作用をも
たない色素あるいは可視光を実質的に吸収しない
物質であつて、強色増感を示す物質を乳剤中に含
んでもよい。たとえば含チツ素異節環基で置換さ
れたアミノスチルベン化合物(たとえば米国特許
2933390号、同3635721号に記載のもの)、芳香族
有機酸ホルムアルデヒド縮合物(たとえば米国特
許3743510号に記載のもの)、カドミウム塩、アザ
インデン化合物などを含んでもよい。米国特許
3615613号、同3615641号、同3617295号、同
3635721号に記載の組合せは特に有用である。
本発明の写真感光材料の写真乳剤層には感度上
昇、コントラスト上昇、または現像促進の目的
で、例えばポリアルキレンオキシドまたはそのエ
ーテル、エステル、アミンなどの誘導体、チオエ
ーテル化合物、チオモルフオリン類、四級アンモ
ニウム塩化合物、ウレタン誘導体、尿素誘導体、
イミダゾール誘導体、3−ピラゾリドン類等を含
んでもよい。例えば米国特許2400532号、同
2423549号、同2716062号、同3617280号、同
3772021号、同3808003号、英国特許1488991号、
等に記載されたものを用いることができる。
写真乳剤の結合剤または保護コロイドとして
は、ゼラチンを用いるのが有利であるが、それ以
外の親水性コロイドも用いることができる。
たとえばゼラチン誘導体、ゼラチンと他の高分
子とのグラフトポリマー、アルブミン、カゼイン
等の蛋白質;ヒドロキシエチルセルロース、カル
ボキシメチルセルロース、セルローズ硫酸エステ
ル類等の如きセルロース誘導体、アルギン酸ソー
ダ、澱粉誘導体などの糖誘導体;ポリビニルアル
コール、ポリビニルアルコール部分アセタール、
ポリ−N−ビニルピロリドン、ポリアクリル酸、
ポリメタクリル酸、ポリアクリルアミド、ポリビ
ニルイミダゾール、ポリビニルピラゾール等の単
一あるいは共重合体の如き多種の合成親水性高分
子物質を用いることができる。
ゼラチンとしては石灰処理ゼラチンのほか酸処
理ゼラチンやBull.Soc.Sci.Phot.JapanNo.16、30頁
(1966)に記載されたような酸素処理ゼラチンを
用いてもよく、又ゼラチンの加水分解物や酸素分
解物も用いることができる。ゼラチン誘導体とし
ては、ゼラチンにたとえば酸ハライド、酸無水
物、イソシアナート類、ブロモ酢酸、アルカンサ
ルトン類、ビニルスルホンアミド類、マレインイ
ミド化合物類、ポリアルキレンオキシド類、エポ
キシ化合物類等種々の化合物を反応させて得られ
るものが用いられる。その具体例は米国特許
2614928号、同3132945号、同3186846号、同
3312553号、英国特許861414号、同1033189号、同
1005784号、特開昭42−26845号などに記載されて
いる。
前記ゼラチン・グラフトポリマーとしては、ゼ
ラチンにアクリル酸、メタアクリル酸、それらの
エステル、アミドなどの誘導体、アクリロニトリ
ル、スチレンなどの如きビニル系モノマーの単一
(ホモ)または共重合体をグラフトさせたものを
用いることができる。ことに、ゼラチンとある程
度相溶性のあるポリマーたとえばアクリル酸、メ
タアクリル酸、アクリルアミド、メタアクリルア
ミド、ヒドロキシアルキルメタアクリレート等の
重合体とのグラフトポリマーが好ましい。これら
の例は米国特許2763625号、同2831767号、同
2956884号などに記載がある。
代表的な合成親水性高分子物質はたとえば西独
特許出願(OLS)2312708号、米国特許3620751
号、同3879205号、特開昭43−7561号に記載のも
のである。
本発明は支持体上に少なくとも2つの異なる分
光感度を有する多層多色写真材料にも適用でき
る。多層天然色写真材料は、通常支持体上に赤感
性乳剤層、および青感性乳剤層を各々少なくとも
一つ有する。これらの層の順序は必要に応じて任
意にえらべる。赤感性乳剤層にシアン形成カプラ
ーを、緑感性乳剤層にマゼンタ形成カプラーを、
青感性乳剤層にイエロー形成カプラーをそれぞれ
含むのが通常であるが、場合により異なる組合せ
をとることもできる。
本発明に用いて作られた感光材料には親水性コ
ロイド層にフイルター染料として、あるいはイラ
ジエーシヨン防止その他種々の目的で、水溶性染
料を含有してよい。このような染料にはオキソノ
ール染料、ヘミオキソノール染料、スチリル染
料、メロシアニン染料、シアニン染料、及びアゾ
染料が包含される。中でもオキソノール染料;ヘ
ミオキソノール染料及びメロシアニン染料が有用
である。用い得る染料の具体例は、英国特許
584609号、同1177429号、特開昭48−85130号、同
49−99620号、同49−114420号、同52−108115
号、米国特許2274782号、同2533472号、同
2956879号、同3148187号、同3177078号、同
3247127号、同3540887号、同3575704号、同
3653905号、同3718472号、同4071312号、同
4070352号に記載されたものである。
本発明を実施するに際して下記の公知の退色防
止剤を併用することもでき、また本発明に用いる
色像安定剤は単独または2種以上併用することも
できる。公知の退色防止剤としては、例えば、米
国特許2360290号、同2418613号、同2675314号、
同2701197号、同2704713号、同2728659号、同
2732300号、同2735765号、同2710、801号、同
2816028号、英国特許1363921号、等に記載された
ハイドロキノン誘導体、米国特許3457079号、同
3069262号、等に記載された没食子酸誘導体、米
国特許2735765号、同3698909号、特公昭49−
20977号、同52−6623号に記載されたp−アルコ
キシフエノール類、米国特許3432300号、同
3573050号、同3574627号、同3764337号、特開昭
52−35633号、同52−147434号、同52−152225号
に記載されたp−オキシフエノール誘導体、米国
特許3700455号に記載のビスフエノール類等があ
る。
本発明を用いて作られる感光材料は色カブリ防
止剤として、ハイドロキノン誘導体、アミノフエ
ノール誘導体、没食子酸誘導体、アスコルビン酸
誘導体などを含有してもよく、その具体例は米国
特許2360290号、同2336327号、同2403721号、同
2418613号、同2675314号、同2701197号、同
2704713号、同2728659号、同2732300号、同
2735765号、特開昭50−92988号、同50−92989
号、同50−93928号、同50−110337号、同52−
146235号、特公昭50−23813号等に記載されてい
る。
本発明を用いて作られる感光材料には親水性コ
ロイド層に紫外線吸収剤を含んでよい。たとえば
アリール基で置換されたベンゾトリアゾール化合
物(たとえば米国特許3533794号に記載のもの)、
4−チアゾリドン化合物(たとえば米国特許
3314794号、同3352681号に記載のもの)、ベンゾ
フエノン化合物(たとえば特開昭46−2784号に記
載のもの)、ケイヒ酸エステル化合物(たとえば
米国特許3705805号、同3707375号に記載のも
の)、ブタジエン化合物(たとえば米国特許
4045229号に記載のもの)あるいはベンゾオキシ
ゾール化合物(たとえば米国特許3700455号に記
載のもの)を用いることができる。さらに米国特
許3499762号、特開昭54−48535号に記載のものも
用いることができる。紫外線吸収性のカプラー
(たとえばα−ナフトール系のシアン色素形成カ
プラー)や紫外線吸収性のポリマーなどを用いて
もよい。これらの紫外線吸収剤は特定の層に媒染
されてもよい。
本発明を用いてつくられる感光材料において、
写真乳剤層その他の親水性コロイド層にはスチル
ベン系、トリアジン系、オキサゾール系、あるい
はクマリン系などの増白剤を含んでもよい。これ
らは水溶性のものでもよく、また水不溶性の増白
剤を分散物の形で用いてもよい。螢光増白剤の具
体例は米国特許2632701号、同3269840号、同
3359102号、英国特許852075号、同1319763号など
に記載されている。
本発明には一般式()で表わされるピラゾロ
ンカプラー以外にも公知のカプラーを使用でき
る。黄色カプラーとしてはベンゾイルアセトアニ
リド系及びピバロイルアセトアニリド系化合物は
有利である。用い得る黄色発色カプラーの具体例
は米国特許2875057号。同3265506号。同3408194
号、同3551155号、同3582322号。同3725072号、
同3891445号。西独特許1547868号、西独出願公開
2219917号、同2261361号、同2414006号、英国特
許1425020号、特公昭51−10783号、特開昭47−
26133号、同48−73147号、同51−102636号、同50
−6341号、同50−123342号、同50−130442号、同
51−21827号、同50−87650号、同52−82424号、
同52−115219号などに記載されたものである。
マゼンタ発色カプラーとしてはピラゾロン系化
合物、インダゾロン系化合物、シアノアセチル化
合物などを用いることができ、特にピラゾロン系
化合物は有利である。用い得るマゼンタ発色カプ
ラーの具体例は、米国特許2600788号、同2983608
号、同3062653号、同3127269号、同3311476号、
同3419391号、同3519429号、同3558319号、同
3582322号、同3615506号、同3834908号、同
3891445号、西独特許1810464号、西独特許出願
(OLS)2408665号、同2417945号、同2418959
号、同2424467号、特公昭40−6031号、特開昭51
−20826号、同52−58922号、同49−129538号、同
49−74024号、同50−159336号、同52−42121号、
同49−74028号、同50−60233号、同51−26541
号、同53−55122号、同などに記載のものであ
る。
シアン発色カプラーとしてはフエノール系化合
物、ナフトール系化合物などを用いることができ
る。その具体例は米国特許2369929号、同2434272
号、同2474293号、同2521908号、同2895826号、
同3034892号、同3311476号、同3458315号、同
3476563号、同3583971号、同3591383号、同
3767411号、同4004929号、西独特許出願
(OLS)2414830号、同2454329号、特開昭48−
59838号、同51−26034号、同48−5055号、同51−
146828号、同52−69624号、同52−90932号に記載
のものである。
カラード・カプラーとしては例えば米国特許
3476560号、同2521908号、同3034892号、特公昭
44−2016号、同38−22335号、同42−11304号、同
44−32461号、特開昭51−26034号明細書、同52−
42121号明細書、西独特許出願(OLS)2418959
号に記載のものを使用できる。
DIRカプラーとしては、たとえば米国特許
3227554号、同3617291号、同3701783号、同
3790384号、同3632345号、西独特許出願
(OLS)2414006号、同2454301号、同2454329
号、英国特許953454号、特開昭52−69624号、同
49−122335号、特公昭51−16141号に記載された
ものが使用できる。
DIRカプラー以外に、現像にともなつて現像抑
制剤を放出する化合物を、感光材料中に含んでも
よく、例えば米国特許3297445号、同3379529号、
西独特許出願(OLS)2417914号、特開昭52−
15271号、特開昭53−9116号に記載のものが使用
できる。
上記のカプラーは同一層に二種以上含むことも
できる。同一の化合物を異なる2つの以上の層に
含んでもよい。
これらのカプラーは、一般に乳剤層中の銀1モ
ルあたり2×10-3モルないし5×10-1モル、好ま
しくは1×10-2モルないし5×10-1モル添加され
る。
本発明を用いて作られる感光材料の写真処理に
は、公知の方法のいずれも用いることができる。
処理液には公知のものを用いることができる。処
理温度は普通18℃から50℃の間に選ばれるが、18
℃より低い温度または50℃をこえる温度としても
よい。
カラー現像液は、一般に発色現像主薬を含むア
ルカリ性水溶液から成る。発色現像主薬は公知の
一級芳香族アミン現像剤、例えばフエニレンジア
ミン類(例えば4−アミノ−N・N−ジエチルア
ニリン、3−メチル−4−アミノ−N・N−ジエ
チルアニリン、4−アミノ−N−エチル−N−β
−ヒドロキシエチルアニリン、3−メチル−4−
アミノ−N−エチル−N−β−ヒドロキシエチル
アニリン、3−メチル−4−アミノ−N−エチル
−N−β−メタンスルホアミドエチルアニリン、
4−アミノ−3−メチル−N−エチル−N−β−
メトキシエチルアニリンなど)を用いることがで
きる。
この他L.F.A.Mason著Photographic
Processing Chemistry(Focal Prese刊、1966
年)の226〜229頁、米国特許2193015号、同
2592364号、特開昭48−64933号などに記載のもの
を用いてよい。
カラー現像剤はそのほかアルカリ金属の亜硫酸
塩、炭酸塩、ホウ酸塩およびリン酸塩の如きPH緩
衝剤、臭化物、沃化物および有機カブリ防止剤の
如き現像抑制剤ないしカブリ防止剤などを含むこ
とができる。また必要に応じて、硬水軟化剤、ヒ
ドロキシルアミンの如き保恒剤、ベンジルアルコ
ール、ジエチレングリコールの如き有機溶剤、ポ
リエチレングリコール、四級アンモニウム塩、ア
ミン類の如き現像促進剤、色素形成カプラー、競
争カプラー、ナトリウムボロハイドライドの如き
かぶらせ剤、1−フエニル−3−ピラゾリドンの
如き補助現像薬、粘性付与剤、米国特許4083723
号に記載のポリカルボン酸系キレート剤、西独公
開(OLS)2622950号に記載の酸化防止剤などを
含んでもよい。
発色現像後の写真乳剤層は通常、漂白処理され
る。漂白処理は定着処理と同時に行なわれてもよ
いし、個別により行なわれてもよい。漂白剤とし
ては鉄()、コバルト()、クロム()、銅
()などの多価金属の化合物、過酸類、キノン
類、ニトロソ化合物などが用いられる。たとえば
フエリシアン化物、重クロム酸塩、鉄()また
はコバルト()の有機錯塩、たとえばエチレン
ジアミン四酢酸、ニトリロトリ酢酸、1・3−ジ
アミノ−2−プロパノール四酢酸などのアミノポ
リカルボン酸類あるいはクエン酸、酒石酸、リン
ゴ酸などの有機酸の錯塩;過硫酸塩、過マンガン
酸塩;ニトロソフエノールなどを用いることがで
きる。これらのうちフエリシアン化カリ、エチレ
ンジアミン四酢酸鉄()ナトリウムおよびエチ
レンジアミン四酢酸鉄()アンモニウムは特に
有用である。エチレンジアミン四酢酸鉄()錯
塩は独立の漂白液においても、一浴漂白定着液に
おいても有用である。
漂白または漂白定着液には、米国特許3042520
号、同3241966号、特公昭45−8506号、特公昭45
−8836号などに記載の漂白促進剤、特開昭53−
65732号に記載のチオール化合物の他、種々の添
加剤を加えることもできる。
本発明を用いて作られた感光材料は特開昭51−
84636号、特開昭52−119934号、特開昭53−46732
号、特開昭54−9626号、特開昭54−19741号、特
開昭54−37731号、特願昭54−76158号、特願昭54
−76159号、特願昭54−102962号に記載された方
法で補述又は維持管理されている現像液で処理さ
れてもよい。
本発明を用いて作られた感光材料に用いられる
漂白定着液は特開昭46−781号、同48−49437号、
同48−18191号、同50−145231号、同51−18541
号、同51−19535号、同51−144620号、特公昭51
−23178号に記載の方法で再生処理したものでも
よい。
実施例 1
透明なセルローストリアセテート支持体上に下
記の組成の塗布組成物を塗布し、この層の上にゼ
ラチン保護層(1g/m2)を塗布して試料A〜G
を作製した。
塗布液組成
緑感性沃臭化銀乳剤(沃化銀6モル%、臭化銀
94モル%、塗布銀量1g/m2)
マゼンタカプラー塗布量7×10-4モル/m2
本発明に係る添加剤化合物(第1表参照)7×
10-5モル/m2
カプラー分散用触媒……トリクレジルホスフエ
ート
The present invention relates to a color photographic material,
This is particularly true for color photographic materials that have a high dye formation yield and increase sensitivity in the color development process. By color-developing silver halide color photographic materials, the oxidized aromatic primary amine color developing agent and coupler react to produce indophenol, indoaniline, indamine, azomethine, etc.
It is known that phenoxazine, phenazine and similar dyes can be produced to form color images. In this system, a subtractive color method is usually used for color reproduction, using silver halide emulsions that are selectively sensitive to blue, green, and red, and color image forming agents of yellow, magenta, and cyan, which are complementary colors, respectively. is used. To form a yellow image, for example, an acylacetanilide or dibenzoylmethane coupler is used, and to form a magenta image, a pyrazolone, pyrazolobenzimidazole, cyanoacetophenone or imidazolone coupler is used. Couplers are used, primarily phenolic couplers such as phenols and naphthols to form cyan images. Most couplers that form conventional color images are 4-equivalent couplers. That is, in order to form 1 mol of dye through a coupling reaction, development using 4 mol of silver halide as an oxidizing agent is theoretically required. In contrast, a 2-equivalent coupler with an active methylene group substituted with a group that oxidatively couples with the oxidation product of an aromatic primary amine developer produces 2 moles of halogenation to form 1 mole of dye. Only silver development is required.
With a 2-equivalent coupler, the amount of silver halide required to form a dye is only half that of a 4-equivalent coupler, so it is possible to speed up the processing of photosensitive materials by making the photosensitive layer thinner, and by reducing the film thickness. Many benefits are recognized in terms of improved photographic properties and economical efficiency. Several attempts have been proposed to make the 5-pyrazolone type coupler, which has been mainly used as a magenta-forming coupler, into two equivalents. For example, in U.S. Pat. No. 3,214,437 and U.S. Pat. No. 3,253,924, the 4-position of the pyrazolone is replaced by a thiocyano group, in U.S. Pat. No. 3,311,476 by an acyloxy group, and in U.S. Pat. Patent No. 3,617,291 describes substitution with a 2-triazolyl group, and US Pat. No. 3,522,052 describes substitution with a halogen atom. However, when these 4-substituted pyrazolone couplers are used, significant color fog may occur, the reaction activity may not be appropriate, or the couplers may be chemically unstable and may not develop color over time. This has been accompanied by some disadvantages, such as the fact that it changes into a substance, and furthermore, there are many difficulties in synthesizing it. It has also been previously known to substitute the 4-position of 5-pyrazolone with an alkylthio group, an arylthio group, or a heterocyclic thio group, as disclosed in US Pat. No. 3,227,554. However, many of these known thio-substituted pyrazolone compounds have inadequate reaction activity with the oxidation products of aromatic primary amine color developers, and furthermore, as a result of the coupling reaction, the resulting mercapto compounds exhibit strong photographic activity. Therefore, it is difficult to apply it to general color photosensitive materials, and the chemical stability of the coupler is also insufficient. Furthermore, the color development sensitivity of the above-mentioned two-equivalent magenta coupler is not necessarily sufficient to meet the recent technical problem of increasing the sensitivity of color photosensitive materials.
There has been a strong desire to develop a technique for increasing the sensitivity of the magenta image forming layer. Recently, it has been found that magenta couplers having an alkylthio leaving group have particularly high activity and high color development sensitivity (see Japanese Patent Application No. 136497-1972).
This is still insufficient to obtain a highly sensitive color light-sensitive material, and in order to further improve this, a technique of using this magenta coupler in combination with a 1-phenyl-3-pyrazolidone derivative has been considered, resulting in even higher sensitivity. It became possible to obtain sensitive photosensitive materials. This also improved the storage stability of 5-pyrazolone couplers having an alkylthio leaving group.
However, this combination technology has a side effect of increased fogging, and solving this problem is essential for putting the above combination technology into practical use. The purpose of the present invention is, firstly, to provide a color photosensitive material with high color development sensitivity of a magenta color image forming layer, a small amount of coated silver, and low fogging, and secondly, to provide a color photosensitive material that has a magenta color image forming layer that is free from alkylthio without increasing fogging. The purpose of this invention is to improve the storage stability of light-sensitive materials using magenta couplers, and the third purpose is to improve the light resistance and fastness of dyes produced from alkylthio separation magenta couplers. A combination of the coupler represented by the general formula () of the present application and a diffusible 1-phenyl-3-pyrazolidone derivative, and a diffusible 1-phenyl-3-pyrazolidone derivative.
- The above object cannot be achieved by a method in which the pyrazolidone derivative is dissolved in a low boiling point organic solvent such as methanol and added to the emulsion. The object of the present invention is to provide a 1-phenyl-3 having a diffusion-resistant group in an emulsion layer containing at least one coupler represented by the following general formula () and/or in a hydrophilic colloid layer adjacent to the emulsion layer. This is achieved by containing a pyrazolidone derivative and a hydroquinone derivative represented by the general formula () in the presence of a high-boiling organic solvent for photographic additives. The present invention includes mixing a coupler represented by the general formula () with a diffusion-resistant oil-soluble 1-phenyl-3-pyrazolidone derivative, dissolving the mixture in a high-boiling organic solvent for photographic additives, and dispersing the mixture in an emulsion layer. It is particularly preferable in that it has a large effect. Coupler represented by general formula (), present application 1-
It is more preferable to mix the phenyl-3-pyrazolidone derivative and the hydroquinone derivative represented by the general formula (), dissolve the mixture in a high-boiling organic solvent, and disperse the mixture in the emulsion layer because the effects of the present invention are even greater. General formula () In the formula, R 1 represents an anilino group, an amylamino group, or a ureido group, R 2 represents an aralkyl group, an alkyl group having 1 to 22 carbon atoms, or an alkenyl group, and X 1 , X 2 , and X 3 represent a hydrogen atom or an alkyl group. group, a halogen atom, an alkoxy group, an aryloxy group, an acylamino group, a carbamoyl group, a sulfamoyl group, a sulfonyl group, or a cyano group, X 1 ,
X 2 and X 3 may be the same group or different groups. More specifically, R 1 is an anilino group (e.g.
Phenylamino group, o-chlorophenylamino group, 2,4-dichlorophenylamino group, 2,4
-dichloro-5-methoxyphenylamino group, 2
-chloro-5-tetradecanamidephenylamino group, 2-chloro-5-{α-(2,4-di-t-
amylphenoxy)butyramide}phenylamino group, 2-chloro-5-{(3-octadecenyl)
succinimide}phenylamino group, 2-chloro-5-[α-{(3-t-butyl-4-hydroxy)phenoxy}tetradecanamide]phenylamino group, etc.), acylamino group (e.g., acetylamino group, butylamide group, α- (3-pentadecylphenoxy)butyramide group, n-tetradecanamide group, α-(2,4-di-t-amylphenoxy)butyramide group, 3-{α-(2.
4-di-t-amylphenoxy)butyramide}
benzamide group, benzamide group, 3-acetylamide benzamide group, etc.), ureido group (e.g. phenylureido group, methylureido group, 3-acetylamidobenzamide group, etc.),
{α-(2,4-di-tert-amylphenoxy)butyramide} phenylureido, etc.), and X 1 , X 2 , and X 3 are hydrogen atoms, alkyl groups (e.g., methyl groups, ethyl groups, etc.), halogen atoms (chloro atom, bromine atom, fluorine atom), alkoxy group (methoxy group, ethoxy group, etc.), aryloxy group (e.g. phenyloxy group, naphthyloxy group, etc.), acylamino group (e.g. acetylamino group, α -(2,4-G-t-
(amylphenoxy)butylamide group, etc.), carbamoyl group (e.g., methylcarbamoyl, phenylcarbamoyl group, etc.), sulfamoyl group (e.g., methylsulfamoyl group, phenylsulfamoyl group, etc.), sulfonyl group (e.g.,
(ethylsulfonyl, butylsulfonyl, methylsulfonyl, etc.), cyano group. R 2 represents a straight chain or branched alkyl group having 1 to 22 carbon atoms,
May be replaced. Examples of substituted alkyl groups are
A methyl group, an ethyl group, a propyl group, a butyl group, an octyl group, a dodecyl group, a tetradecyl group, an octadecyl group, or a heptadecyl group. Examples of branched alkyl groups are i-propyl and tert-butyl. Furthermore, R 2 represents an aralkyl group (eg, benzyl group, 2-phenylethyl group) or an alkenyl group (eg, propenyl group). These alkyl groups, aralkyl groups and alkenyl groups each have a halogen atom, nitro, cyano, aryl,
alkoxy, aryloxy, carboxy, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, acyloxy, sulfamoyl, carbamoyl, acylamino, diacylamino, ureido, thioureido, urethane, thiourethane, sulfonamide, heterocycle, arylsulfonyloxy, Alkylsulfonyloxy, arylsulfonyl, alkylsulfonyl, arylthio, alkylthio,
Alkylsulfinyl, arylsulfinyl,
alkylamino, dialkylamino, anilino,
N-arylanilino, N-alkylanilino,
It may be substituted with a substituent selected from N-acylanilino and hydroxy groups. Among those represented by the general formula (), couplers in which R 2 is an alkyl group having 1 to 5 carbon atoms are particularly preferred in that the resulting dye has high fastness. Regarding the physical properties and manufacturing method of specific examples of the coupler represented by the general formula (), please refer to Japanese Patent Application No. 53-136497.
(Japanese Unexamined Patent Publication No. 55-62454). The general formula () of the present invention is as follows. General formula () R represents an alkyl group having 8 to 30 carbon atoms, an aryl group, an alkoxy group, an aryloxy group, a carbamoyl group, a sulfamoyl group, an alkoxycarbonyl group, or an aryloxycarbonyl group. Among the above alkyl groups and aryl groups, halogen atoms, alkyl groups, aryl groups, alkoxy groups, aryloxy groups, carboxyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, acyl groups, acyloxy groups, carbamoyl groups, sulfo groups, Sulfamoyl group, sulfonamide group, N-
It may have a substituent such as an alkylamino group, an N-arylamino group, an acylamino group, an imide group, or a hydroxyl group. n represents a number from 1 to 4, and when n is 2 or more,
Each R may be the same or different. Specific examples of the compound represented by the general formula () are as follows. HQ-1 2,5-di-tert-octylhydroquinone HQ-2 2-tert-octyl-5-methylhydroquinone HQ-3 2,6-di-n-dodecyl-hydroquinone HQ-4 2-n-dodecylhydroquinone HQ -5 2,2'-methylenebis-5,5'-di-
tert-Butylhydroquinone HQ-6 2,5-di-n-octylhydroquinone HQ-7 2-dodecylcarbamoylhydroquinone HQ-8 2-(β-n-dodecyloxycarbonyl)ethylhydroquinone HQ-9 2-(N・N -dibutylcarbamoyl)hydroquinone HQ-10 2-n-dodecyl-5-chlorohydroquinone HQ-11 2-(2-octadecyl)-5-methylhydroquinone HQ-12 2,5-di-(p-methoxyphenyl)hydroquinone HQ-13 2-tert-octylhydroquinone HQ-14 2-[β-{3-(3-sulfobenzamide)benzamide}ethylhydroquinone HQ-15 2,5-dichloro-3,6-diphenylhydroquinone HQ-16 2・6-dimethyl-3-tert-octylhydroquinone HQ-17 2,3-dimethyl-5-tert-octylhydroquinone HQ-18 2-{β-(dodecanoyloxy)ethyl}carbamoylhydroquinone HQ-19 2-dodecyloxy Carbonylhydroquinone HQ-20 2-{β-(4-octanamidophenyl)ethyl}hydroquinone HQ-21 2-methyl-5-dodecylhydroquinone HQ-22 2,5-di-tert-hexylhydroquinone Used in the present invention These 1-phenyl-3-pyrazolidone derivatives can be used alone or in combination of two or more. The amount added is preferably 0.005 mol to 10 mol, preferably 0.01 mol to 2 mol, per mol of the 2-equivalent magenta coupler. The 1-phenyl-3-pyrazolidone derivatives of the present invention include those represented by the general formula (). General formula () In the formula, R 3 represents an optionally substituted aryl group, and examples of the substituent include a halogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxy group,
Examples include aryloxy group, alkylthio group, arylthio group, acylamino group, nitro group, sulfonamino group, cyano group, hydroxyl group, sulfo group, carboxyl group, and alkyloxycarbonyl group, and particularly preferred ones include alkoxy group, aryloxy group, and alkylthio group. and arylthio groups.
R 4 to R 7 each represent a hydrogen atom, an alkyl group, a substituted alkyl group, (substituents include an aryl group, a hydroxyl group,
halogen atom, acyloxy group, alkyloxy group, aryloxy group, alkylthio group, arylthio group, heterocyclic group) aryl group, substituted aryl group (substituents include alkyl group, aryl group,
halogen atom, alkyloxy group, aryloxy group, alkylthio group, arylthio group, amino group, alkylamino group, acylamino group, sulfonamino group, cyano group, nitro group, hydroxyl group), alkyloxy group, aryloxy group, or aralkyloxy represents a group. However, if each of R 4 to R 7 has a carbon number of 6 or less, the aryl group of R 3 has a substituent with a carbon number of 6 or more, and if R 3 has a substituent with a carbon number of 6 or less, At least one of R 4 to R 7 has 6 or more carbon atoms. The high boiling point organic solvent for photographic additives used in the present invention may be any known one, such as phthalic acid alkyl esters (dibutyl phthalate, dioctyl phthalate, etc.), phosphoric esters (diphenyl phthalate, etc.) described in US Pat. No. 2,322,027, and phosphates, triphenyl phosphate, tricresyl phosphate, dioctyl butyl phosphate), citric acid esters (e.g. acetyl tributyl citrate), benzoic acid esters (e.g. octyl benzoate), alkyl amides (e.g. diethyl laurylamide), fatty acid esters (e.g. dibutoxyethyl succinate, dioctyl azelate), trimesic acid esters (e.g. tributyl trimesate), etc., such as U.S. Pat.
No. 2835579, Special Publication No. 46-23233, U.S. Patent
No. 3287134, British Patent No. 958441, Japanese Unexamined Patent Publication No. 1973-
1031, UK Patent No. 1222753, US Patent No. 3936303,
JP-A-51-26037, JP-A-50-82078, US Pat. No. 2353262, US Pat. No. 285238, US Pat. No. 3554755,
No. 3676137, No. 3676142, No. 3700454, No.
No. 3748141, No. 3837863, OLS2538889, JP-A No. 51-27921, No. 51-27922, No. 51-26035
No. 51-26036, No. 50-62632, Japanese Unexamined Patent Publication No. 1973-
Also preferred are those described in US Pat. No. 29461, US Pat. No. 3,936,303, US Pat. To introduce a coupler or a 1-phenyl-3-pyrazolidone derivative into a hydrophilic colloid layer, the method described in US Pat. After being dissolved in an organic solvent, such as a lower alkyl acetate such as ethyl acetate or butyl acetate, ethyl fropionate, secondary butyl alcohol, methyl isobutyl ketone, β-ethoxyethyl acetate, or methyl cellosolve acetate, it is dispersed in a hydrophilic colloid. . The above-mentioned high boiling point organic solvent and low boiling point organic solvent may be mixed and used. Further, the dispersion method using a polymer described in Japanese Patent Publication No. 51-39853 and Japanese Patent Application Laid-open No. 51-59943 can also be used. When the coupler has an acid group such as carboxylic acid or sulfonic acid, it is introduced into the hydrophilic colloid as an alkaline aqueous solution. A technique similar to the present invention is disclosed in Japanese Patent Application Laid-Open No. 130928/1983. However, this technology is not for 5-pyrazolone magenta couplers, but for pyrazole magenta couplers in which the 5th position of the ring is substituted with a sulfonyloxy group or a carbonyloxy group, rather than an oxo group, and it is clear from the data in the examples. In this coupler, the general formula of the present invention is ()
It is clearly distinguished from the present invention in that there is almost no effect of increasing color development sensitivity even when used in combination with the compound of
Moreover, it is truly unexpected that there is such a difference in effectiveness. The photographic emulsion used in the present invention is written by P. Glafkides.
Chimie et Physique Photographique (Paul
Montel Publishing, 1967), GFDuffin
Photographic Emulsion Chemistry (The Focal
Press, 1966), VLZelikman et al.
Making and Coating Photographic Emulsion
(The Focal Press, 1964). That is, any of the acidic method, neutral method, ammonia method, etc. may be used, and the methods for reacting the soluble silver salt and soluble halogen salt include one-sided mixing method, simultaneous mixing method,
Any combination thereof may be used. It is also possible to use a method in which particles are formed in an excess of silver ions (so-called back-mixing method).
As one type of simultaneous mixing method, a method in which the pAg in the liquid phase in which silver halide is produced can be kept constant, that is, a so-called controlled double jet method can also be used. According to this method, a silver halide emulsion having a regular crystal shape and a nearly uniform grain size can be obtained. Two or more types of silver halide emulsions formed separately may be mixed and used. In the process of silver halide grain formation or physical ripening, a cadmium salt, a zinc salt, a lead salt, a thallium salt, an iridium salt or a complex salt thereof, a rhodium salt or a complex salt thereof, an iron salt or an iron complex salt, etc. may be present. The photographic emulsions used in this invention may be spectrally sensitized with methine dyes and others. The dyes used include cyanine dyes, merocyanine dyes, complex cyanine dyes, complex merocyanine dyes, holopolar cyanine dyes, hemicyanine dyes, styryl dyes, and hemioxonol dyes. Particularly useful dyes are those belonging to the cyanine dyes, merocyanine dyes and complex merocyanine dyes. Any of the nuclei commonly used for cyanine dyes can be used as the basic heterocyclic nucleus for these dye numbers. That is, pyrroline nucleus, oxazoline nucleus, thiazoline nucleus, pyrrole nucleus, oxazole nucleus, thiazole nucleus, selenazole nucleus, imidazole nucleus, tetrazole nucleus, pyridine nucleus, etc.; nuclei in which an alicyclic hydrocarbon ring is fused to these nuclei; and these A nucleus in which an aromatic hydrocarbon ring is fused to the nucleus, i.e., indolenine nucleus, benzindolenine nucleus, indole nucleus, benzoxazole nucleus, naphthoxazole nucleus, benzothiazole nucleus, naphthothiazole nucleus, benzoselenazole nucleus, benzimidazole Nuclei, quinoline nuclei, etc. can be applied. These nuclei may be substituted on carbon atoms. The merocyanine dye or composite merocyanine dye includes a pyrazolin-5-one nucleus, a thiohydantoin nucleus, a 2-thioxazolidine-2,4-dione nucleus, a thiazolidine-2,4-dione nucleus, a rhodanine nucleus, as a nucleus having a ketomethylene structure. A 5- to 6-membered heteroartic ring nucleus such as a thiobarbituric acid nucleus can be applied. Useful sensitizing dyes include, for example, German Patent No. 929080;
US Patent No. 2231658, US Patent No. 2493748, US Patent No. 2503776
No. 2519001, No. 2912329, No. 3656959,
Same No. 3672897, No. 3694217, No. 4025349, Same No.
No. 4046572, British Patent No. 1242588, Special Publication No. 1977-
No. 14030, No. 52-24844. These sensitizing dyes may be used alone or in combination, and combinations of sensitizing dyes are often used particularly for the purpose of supersensitization. Typical examples are US Patent No. 2688545, US Patent No. 2977229, US Patent No.
No. 3397060, No. 3522052, No. 3527641, No. 3527641, No. 3522052, No. 3527641, No.
No. 3617293, No. 3628964, No. 3666480, No.
No. 3672898, No. 3679428, No. 3703377, No. 3672898, No. 3679428, No. 3703377, No.
No. 3769301, No. 3814609, No. 3837862, No. 3837862, No. 3814609, No. 3837862, No.
4026707, British Patent No. 1344281, British Patent No. 1507803,
Special Publication No. 43-4936, No. 53-12375, Japanese Patent Publication No. 52-
No. 110618 and No. 52-109925. Along with the sensitizing dye, the emulsion may contain a dye that itself does not have a spectral sensitizing effect or a substance that does not substantially absorb visible light and exhibits supersensitization. For example, aminostilbene compounds substituted with nitrogen-containing heterocyclic groups (e.g.,
2933390 and 3635721), aromatic organic acid formaldehyde condensates (for example, those described in US Pat. No. 3743510), cadmium salts, azaindene compounds, and the like. US patent
No. 3615613, No. 3615641, No. 3617295, No. 3615613, No. 3615641, No. 3617295, No.
The combination described in No. 3635721 is particularly useful. The photographic emulsion layer of the photographic light-sensitive material of the present invention contains, for example, polyalkylene oxide or its derivatives such as ethers, esters, and amines, thioether compounds, thiomorpholins, and quaternary ammonium salts for the purpose of increasing sensitivity, increasing contrast, or accelerating development. compounds, urethane derivatives, urea derivatives,
It may also contain imidazole derivatives, 3-pyrazolidones, and the like. For example, U.S. Patent No. 2400532,
No. 2423549, No. 2716062, No. 3617280, No.
No. 3772021, No. 3808003, British Patent No. 1488991,
Those described in, etc. can be used. Gelatin is advantageously used as a binder or protective colloid in photographic emulsions, but other hydrophilic colloids can also be used. For example, gelatin derivatives, graft polymers of gelatin and other polymers, proteins such as albumin and casein; cellulose derivatives such as hydroxyethyl cellulose, carboxymethyl cellulose, and cellulose sulfates; sugar derivatives such as sodium alginate and starch derivatives; polyvinyl alcohol , polyvinyl alcohol partial acetal,
Poly-N-vinylpyrrolidone, polyacrylic acid,
A wide variety of synthetic hydrophilic polymeric materials can be used, such as single or copolymers of polymethacrylic acid, polyacrylamide, polyvinylimidazole, polyvinylpyrazole, and the like. In addition to lime-treated gelatin, acid-treated gelatin and oxygen-treated gelatin as described in Bull.Soc.Sci.Phot.Japan No. 16, p. 30 (1966) may also be used as the gelatin. or oxygen decomposition products can also be used. As gelatin derivatives, various compounds such as acid halides, acid anhydrides, isocyanates, bromoacetic acids, alkanesultones, vinyl sulfonamides, maleimide compounds, polyalkylene oxides, and epoxy compounds can be added to gelatin. The product obtained by the reaction is used. A specific example is a US patent
No. 2614928, No. 3132945, No. 3186846, No. 3186846, No. 3132945, No. 3186846, No.
3312553, British Patent No. 861414, British Patent No. 1033189, British Patent No.
It is described in No. 1005784, JP-A-42-26845, etc. The gelatin graft polymer is a gelatin grafted with a single (homo) or copolymer of vinyl monomers such as acrylic acid, methacrylic acid, derivatives thereof such as esters and amides, acrylonitrile, and styrene. can be used. Particularly preferred are graft polymers with polymers which are compatible with gelatin to some extent, such as acrylic acid, methacrylic acid, acrylamide, methacrylamide, hydroxyalkyl methacrylates and the like. Examples of these are U.S. Pat.
It is described in issues such as No. 2956884. Typical synthetic hydrophilic polymer substances include West German Patent Application (OLS) No. 2312708 and U.S. Patent No. 3620751.
No. 3,879,205, and Japanese Patent Application Laid-open No. 7561/1983. The invention is also applicable to multilayer, multicolor photographic materials having at least two different spectral sensitivities on the support. Multilayer natural color photographic materials usually have at least one red-sensitive emulsion layer and at least one blue-sensitive emulsion layer on a support. The order of these layers can be arbitrarily selected as necessary. a cyan-forming coupler in the red-sensitive emulsion layer, a magenta-forming coupler in the green-sensitive emulsion layer,
It is usual that each blue-sensitive emulsion layer contains a yellow-forming coupler, but different combinations may be used depending on the case. The photosensitive material prepared according to the present invention may contain a water-soluble dye in the hydrophilic colloid layer as a filter dye or for various purposes such as preventing irradiation. Such dyes include oxonol dyes, hemioxonol dyes, styryl dyes, merocyanine dyes, cyanine dyes, and azo dyes. Among them, oxonol dyes; hemioxonol dyes and merocyanine dyes are useful. Specific examples of dyes that can be used are listed in the British patent
No. 584609, No. 1177429, Unexamined Japanese Patent Publication No. 1977-85130, No.
No. 49-99620, No. 49-114420, No. 52-108115
No., U.S. Patent No. 2274782, U.S. Patent No. 2533472, U.S. Patent No.
No. 2956879, No. 3148187, No. 3177078, No.
No. 3247127, No. 3540887, No. 3575704, No.
No. 3653905, No. 3718472, No. 4071312, No. 3653905, No. 3718472, No. 4071312, No.
It is described in No. 4070352. In carrying out the present invention, the following known antifading agents may be used in combination, and the color image stabilizers used in the present invention may be used alone or in combination of two or more. Known anti-fading agents include, for example, U.S. Pat.
2701197, 2704713, 2728659, 2701197, 2704713, 2728659,
No. 2732300, No. 2735765, No. 2710, No. 801, No.
Hydroquinone derivatives described in No. 2816028, British Patent No. 1363921, etc., U.S. Patent No. 3457079,
Gallic acid derivatives described in US Pat. No. 3069262, etc., US Pat. No. 2735765, US Pat.
p-alkoxyphenols described in US Pat. No. 20977 and US Pat. No. 52-6623, US Pat.
No. 3573050, No. 3574627, No. 3764337, JP-A-Sho
Examples include p-oxyphenol derivatives described in No. 52-35633, No. 52-147434, and No. 52-152225, and bisphenols described in U.S. Pat. The light-sensitive material produced using the present invention may contain a hydroquinone derivative, an aminophenol derivative, a gallic acid derivative, an ascorbic acid derivative, etc. as a color antifogging agent, and specific examples thereof include US Pat. No. 2,360,290 and US Pat. , No. 2403721, same
No. 2418613, No. 2675314, No. 2701197, No.
No. 2704713, No. 2728659, No. 2732300, No.
No. 2735765, Japanese Patent Publication No. 50-92988, No. 50-92989
No. 50-93928, No. 50-110337, No. 52-
It is described in No. 146235, Special Publication No. 50-23813, etc. The photosensitive material produced using the present invention may contain an ultraviolet absorber in the hydrophilic colloid layer. For example, benzotriazole compounds substituted with aryl groups (such as those described in U.S. Pat. No. 3,533,794),
4-thiazolidone compounds (e.g. U.S. patent
3314794 and 3352681), benzophenone compounds (for example, those described in JP-A-46-2784), cinnamic acid ester compounds (for example, those described in U.S. Pat. No. 3705805 and 3707375), butadiene compounds (e.g. U.S. patents)
4,045,229) or benzoxyzole compounds (eg, those described in US Pat. No. 3,700,455). Further, those described in US Pat. No. 3,499,762 and Japanese Patent Application Laid-Open No. 54-48535 can also be used. An ultraviolet absorbing coupler (for example, an α-naphthol cyan dye-forming coupler) or an ultraviolet absorbing polymer may also be used. These UV absorbers may be mordanted into certain layers. In the photosensitive material produced using the present invention,
The photographic emulsion layer and other hydrophilic colloid layers may contain a stilbene-based, triazine-based, oxazole-based, or coumarin-based brightener. These brighteners may be water-soluble, or water-insoluble brighteners may be used in the form of a dispersion. Specific examples of fluorescent whitening agents are U.S. Pat. No. 2,632,701, U.S. Pat.
It is described in British Patent No. 3359102, British Patent No. 852075, British Patent No. 1319763, etc. In the present invention, known couplers can be used in addition to the pyrazolone coupler represented by the general formula (). Preferred yellow couplers are benzoylacetanilide and pivaloylacetanilide compounds. A specific example of a yellow coupler that can be used is US Pat. No. 2,875,057. Same number 3265506. 3408194
No. 3551155, No. 3582322. No. 3725072,
Same number 3891445. West German patent number 1547868, West German application published
No. 2219917, No. 2261361, No. 2414006, British Patent No. 1425020, Japanese Patent Publication No. 10783, Japanese Patent Publication No. 1977-
No. 26133, No. 48-73147, No. 51-102636, No. 50
-6341, 50-123342, 50-130442, 50-123342, 50-130442,
No. 51-21827, No. 50-87650, No. 52-82424,
This is described in No. 52-115219, etc. As the magenta coloring coupler, pyrazolone compounds, indazolone compounds, cyanoacetyl compounds, etc. can be used, and pyrazolone compounds are particularly advantageous. Specific examples of magenta coloring couplers that can be used include U.S. Pat.
No. 3062653, No. 3127269, No. 3311476,
3419391, 3519429, 3558319, 3519391, 3519429, 3558319,
No. 3582322, No. 3615506, No. 3834908, No.
3891445, West German Patent No. 1810464, West German Patent Application (OLS) No. 2408665, OLS No. 2417945, OLS No. 2418959
No. 2424467, Special Publication No. 1973-6031, Japanese Patent Publication No. 1973
-20826, 52-58922, 49-129538, 52-58922, 49-129538,
No. 49-74024, No. 50-159336, No. 52-42121,
No. 49-74028, No. 50-60233, No. 51-26541
No. 53-55122, No. 53-55122, etc. As the cyan color-forming coupler, a phenol compound, a naphthol compound, etc. can be used. Specific examples are US Patent Nos. 2369929 and 2434272.
No. 2474293, No. 2521908, No. 2895826,
Same No. 3034892, No. 3311476, No. 3458315, Same No.
No. 3476563, No. 3583971, No. 3591383, No. 3591383, No. 3583971, No. 3591383, No.
No. 3767411, No. 4004929, West German Patent Application (OLS) No. 2414830, No. 2454329, JP-A-1977-
No. 59838, No. 51-26034, No. 48-5055, No. 51-
These are those described in No. 146828, No. 52-69624, and No. 52-90932. As a colored coupler, for example, a US patent
No. 3476560, No. 2521908, No. 3034892, Tokko Akira
No. 44-2016, No. 38-22335, No. 42-11304, No. 42-11304, No.
No. 44-32461, JP-A No. 51-26034, No. 52-
Specification No. 42121, West German Patent Application (OLS) 2418959
You can use those listed in the issue. As a DIR coupler, for example, the US patent
No. 3227554, No. 3617291, No. 3701783, No. 3227554, No. 3617291, No. 3701783, No.
3790384, 3632345, West German patent application (OLS) 2414006, 2454301, 2454329
No., British Patent No. 953454, Japanese Unexamined Patent Publication No. 52-69624, same.
Those described in No. 49-122335 and Japanese Patent Publication No. 51-16141 can be used. In addition to the DIR coupler, the light-sensitive material may also contain a compound that releases a development inhibitor during development; for example, U.S. Pat.
West German Patent Application (OLS) No. 2417914, Japanese Unexamined Patent Publication No. 1983-
Those described in No. 15271 and JP-A-53-9116 can be used. Two or more of the above couplers can be contained in the same layer. The same compound may be included in two or more different layers. These couplers are generally added in an amount of 2 x 10 -3 mol to 5 x 10 -1 mol, preferably 1 x 10 -2 mol to 5 x 10 -1 mol, per mol of silver in the emulsion layer. Any known method can be used for photographic processing of the light-sensitive material produced using the present invention.
A known treatment liquid can be used. The processing temperature is usually chosen between 18℃ and 50℃, but 18
The temperature may be lower than °C or higher than 50 °C. Color developers generally consist of an alkaline aqueous solution containing a color developing agent. The color developing agent is a known primary aromatic amine developer, such as phenylene diamines (e.g. 4-amino-N.N-diethylaniline, 3-methyl-4-amino-N.N-diethylaniline, 4-amino- N-ethyl-N-β
-Hydroxyethylaniline, 3-methyl-4-
Amino-N-ethyl-N-β-hydroxyethylaniline, 3-methyl-4-amino-N-ethyl-N-β-methanesulfamide ethylaniline,
4-amino-3-methyl-N-ethyl-N-β-
methoxyethylaniline, etc.) can be used. Other Photography by LFAMason
Processing Chemistry (Focal Prese, 1966)
), pages 226-229, U.S. Patent No. 2193015,
Those described in No. 2592364, JP-A-48-64933, etc. may be used. Color developers may also contain PH buffering agents such as alkali metal sulfites, carbonates, borates and phosphates, development inhibitors or antifoggants such as bromides, iodides and organic antifoggants. can. If necessary, water softeners, preservatives such as hydroxylamine, organic solvents such as benzyl alcohol and diethylene glycol, development accelerators such as polyethylene glycol, quaternary ammonium salts, and amines, dye-forming couplers, competitive couplers, Fogging agents such as sodium borohydride, auxiliary developers such as 1-phenyl-3-pyrazolidone, viscosity-imparting agents, US Pat. No. 4,083,723
It may also contain a polycarboxylic acid chelating agent described in No. 1, an antioxidant described in OLS No. 2622950, and the like. After color development, the photographic emulsion layer is usually bleached. Bleaching treatment may be performed simultaneously with fixing treatment, or may be performed separately. As bleaching agents, compounds of polyvalent metals such as iron (), cobalt (), chromium (), copper (), peracids, quinones, nitroso compounds, etc. are used. For example, ferricyanide, dichromate, organic complex salts of iron () or cobalt (), aminopolycarboxylic acids such as ethylenediaminetetraacetic acid, nitrilotriacetic acid, 1,3-diamino-2-propanoltetraacetic acid, or citric acid, tartaric acid. , complex salts of organic acids such as malic acid; persulfates, permanganates; nitrosophenols, and the like can be used. Of these, potassium ferricyanide, sodium ferric ethylenediaminetetraacetate, and ammonium ferric ethylenediaminetetraacetate are particularly useful. Ethylenediaminetetraacetic acid iron() complex salts are useful in both stand-alone bleach solutions and single bath bleach-fix solutions. Bleach or bleach-fix solution has US Patent 3042520
No. 3241966, Special Publication No. 1977-8506, Special Publication No. 1973
- Bleaching accelerator described in No. 8836, etc., JP-A-53-
In addition to the thiol compound described in No. 65732, various additives can also be added. The photosensitive material made using the present invention is
No. 84636, JP-A-52-119934, JP-A-53-46732
No. 1986-9626, 1974-19741, 1973-37731, Japanese Patent Application No. 1976-76158, Japanese Patent Application No. 54-1976
It may be processed with a developing solution supplemented or maintained by the method described in Japanese Patent Application No. 76159 and Japanese Patent Application No. 54-102962. Bleach-fixing solutions used in photosensitive materials made using the present invention are disclosed in Japanese Patent Application Laid-open Nos. 46-781 and 48-49437;
No. 48-18191, No. 50-145231, No. 51-18541
No. 51-19535, No. 51-144620, Special Publication No. 51
It may also be recycled using the method described in No.-23178. Example 1 A coating composition having the following composition was coated on a transparent cellulose triacetate support, and a gelatin protective layer (1 g/m 2 ) was coated on top of this layer to form samples A to G.
was created. Coating liquid composition Green-sensitive silver iodobromide emulsion (silver iodide 6 mol%, silver bromide
94 mol%, coated silver amount 1 g/m 2 ) Magenta coupler coated amount 7×10 −4 mol/m 2 Additive compound according to the present invention (see Table 1) 7×
10 -5 mol/m 2 Coupler dispersion catalyst...tricresyl phosphate
【表】
上記試料に加え、塗布液組成物に添加剤、化合
物を含まないほかは上記と全く同じ塗布試料を種
作製した。これらを前記試料と対応させて試料
A′〜G′とした。
かぶり防止剤としてHQ−1を用い、添加量を
マゼンタカプラーの1/5モル%とした以外は、試
料A〜Gと同じ塗布試料を作製し、それぞれ
A″〜G″とした。
比較カプラー1
比較カプラー2
比較カプラー3
これらの試料に光学的クサビを通して露光を与
えたのち次の如き処理を施した。
処理工程 温度(℃) 時 間
1 発色現像 38℃ 3分15秒
2 漂 白 〃 6分30秒
3 水 洗 〃 2分
4 定 着 〃 4分
5 水 洗 〃 4分
6 安定浴 〃 1分
用いた処理液は次の組成を有する。
発色現像液
4−アミノ−N−エチル−N−(β−メタンスル
ホンアミドエチル)アニリンモノサルフエート
5g
亜硫酸ナトリウム 5g
ヒドロキシルアミン硫酸塩 2g
炭酸カリウム 30g
炭酸水素カリウム 1.2g
臭化カリウム 1.2g
塩化ナトリウム 0.2g
ニトリロトリ酢酸3ナトリウム 1.2g
PHを10.1に調節し水を加えて全量 1000ml
漂白液
エチレンジアミン4酢酸鉄()アンモニウム
100g
エチレンジアミン4酢酸2ナトリウム 10g
臭化カリウム 150g
氷酢酸 10g
アンモニア水でPHを6.0に調整し水を加えて全量
1
定着液
チオ硫酸アンモニウム 150g
亜硫酸ナトリウム 10g
亜硫酸水素ナトリウム 2.5g
PHを6.0に調整し水を加えて全量 1
安定浴
ホルマリン(37%)
富士ドライウエル 3ml
水を加えて全量 1
処理済試料の濃度を緑色光を用いて測定し、か
ぶり値およびASA感度表示法によつて感度を求
めた。ついで添加剤もハイドロキノン類も含まな
い試料(例えばA′)に対する添加剤のみを加え
た試料(例えばA)の感度比(これをS/S′とす
る)及び添加剤もハイドロキノン類も含まない試
料に対する添加剤及びハイドロキノン類を含む試
料(例えばA″)の感度比(これをS″/S′とす
る)を求めた。これをまとめると第2表のように
なる。[Table] In addition to the above samples, a seed coating sample was prepared which was exactly the same as above except that no additives or compounds were included in the coating liquid composition. Sample these by matching them with the above sample.
A′ to G′. The same coated samples as Samples A to G were prepared, except that HQ-1 was used as the antifoggant and the amount added was 1/5 mol% of the magenta coupler.
A″~G″. Comparison coupler 1 Comparison coupler 2 Comparison coupler 3 These samples were exposed to light through an optical wedge and then subjected to the following treatments. Processing process Temperature (℃) Time 1 Color development 38℃ 3 minutes 15 seconds 2 Bleaching 〃 6 minutes 30 seconds 3 Washing with water 〃 2 minutes 4 Fixing 〃 4 minutes 5 Washing with water 〃 4 minutes 6 Stabilizing bath 〃 1 minute The treatment solution used had the following composition. Color developer 4-amino-N-ethyl-N-(β-methanesulfonamidoethyl)aniline monosulfate
5g Sodium sulfite 5g Hydroxylamine sulfate 2g Potassium carbonate 30g Potassium hydrogen carbonate 1.2g Potassium bromide 1.2g Sodium chloride 0.2g Trisodium nitrilotriacetate 1.2g Adjust the pH to 10.1 and add water to make a total volume of 1000ml Bleach solution Ethylenediamine tetraacetic acid iron () ammonium
100g Ethylenediaminetetraacetic acid disodium 10g Potassium bromide 150g Glacial acetic acid 10g Adjust the pH to 6.0 with ammonia water and add water to make the entire volume.
1 Fixer ammonium thiosulfate 150g Sodium sulfite 10g Sodium hydrogen sulfite 2.5g Adjust the pH to 6.0 and add water to total volume 1 Stable bath formalin (37%) Fuji Drywell 3ml Add water to total volume 1 Indicate the concentration of the processed sample in green Measurements were made using light, and the sensitivity was determined using the fog value and the ASA sensitivity display method. Next, the sensitivity ratio (this is referred to as S/S') of the sample containing only the additive (for example, A) to the sample containing neither the additive nor the hydroquinones (for example, A'), and the sample containing neither the additive nor the hydroquinones. The sensitivity ratio (this is referred to as S''/S') of a sample containing an additive and hydroquinones (for example, A'') was determined. This can be summarized as shown in Table 2.
【表】
上記の如く、比較的活性の低いオキシ離脱型お
よび4・5−ジ置換ピラゾール型カプラーについ
ては、フエニドン添加によるかぶり増加は少ない
が、同時に感度増加もわずかである。
一方、本発明に係る高活性アルキルチオ離脱型
カプラーにおいてはフエニドン添加時のかぶり上
昇は大きいが、かぶり防止剤添加でかぶりを抑制
し、かつ感度上昇を維持することができる。
さらに試料A、A′、A″、C、C′、C″について
塗布後、自然条件下(25℃、60%RH)で3ケ月
間保存した試料を露光・現像処理して得られたマ
ゼンタ色画像の最大濃度を、これらの試料の塗布
直後の最大濃度と比較した。結果は次下の通りで
ある。[Table] As mentioned above, for the oxy-eliminating type and 4,5-disubstituted pyrazole type couplers, which have relatively low activity, the increase in fog due to the addition of phenidone is small, but at the same time, the increase in sensitivity is also small. On the other hand, in the highly active alkylthio splitting coupler according to the present invention, the increase in fog when phenidone is added is large, but the fog can be suppressed by adding an antifoggant and the increase in sensitivity can be maintained. Furthermore, magenta was obtained by exposing and developing samples A, A', A'', C, C', and C'' which were stored for 3 months under natural conditions (25℃, 60%RH) after coating. The maximum density of the color images was compared to the maximum density of these samples immediately after application. The results are as follows.
【表】
上表より本願の試料はかぶりが低く、且つ保存
性のすぐれていることがわかる。
実施例 2
実施例1で使用した乳剤のかわりに3モル%の
ヨードを含む沃臭化銀乳剤(乳剤1Kgあたりハロ
ゲン化銀100g、ゼラチン70gを含む)を使用し
た以外は実施例1と同様のカプラー、および添加
剤を含む塗布試料を作製し、下記の如き反転処理
を施したところ、実施例1と同様、S離脱型2当
量マゼンタカプラーにフエニドン化合物を添加し
たときのかぶりの増加を大きな減感を伴なうこと
なく有効に防ぐことがわかつた。
処理工程 温度(℃) 時間(分)
1 第1現像 38℃ 3
2 水 洗 〃 1
3 反 転 〃 2
4 発色現像 〃 4
5 調 整 〃 2
6 漂 白 38℃ 6
7 定 着 〃 4
8 水 洗 〃 4
9 安 定 〃 1
10 乾 燥
処理した処理液は次の組成を有している。
第1現像液
水 800ml
テトラポリリン酸ナトリウム 2.0g
重亜硫酸ナトリウム 8.0g
亜硫酸ナトリウム 37.0g
1−フエニル−3−ピラゾリドン 0.38g
ハイドロキノン 5.5g
炭酸ナトリウム(一水塩) 28.0g
臭化カリウム 1.5g
沃化カリウム 13.0mg
チオシアン酸ナトリウム 1.4g
水を加えて全量 1
反転液
水 800ml
ニトリロ−N・N・N−トリメチレンホスホン酸
6ナトリウム 3.0g
塩化第一スズ(2水塩) 1.0g
水酸化ナトリウム 8.0g
氷酢酸 15.0ml
水を加えて全量 1.0
発色現像液
水 800ml
テトラポリリン酸ナトリウム 2.0g
ベンジルアルコール 5.0ml
亜硫酸ナトリウム 7.5g
第3リン酸ナトリウム(12水塩) 36.0g
臭化カリウム 1.0g
沃化カリウム 90.0mg
水酸化ナトリウム 3.0g
シトラジン酸 1.5g
4−アミノ−3−メチル−N−エチル−β−ヒド
ロキシエチルアニリンセスキサルフエートモノハ
イドレート 11.0g
エチレンジアミン 3.0g
水を加えて全量 1.0
調整液
水 800ml
氷酢酸 5.0ml
水酸化ナトリウム 3.0g
ジメチルアミノエタンイソチオ尿素(2塩酸塩)
1.0g
水を加えて全量 1
漂白液
水 800ml
エチレンジアミンテトラ酢酸ナトリウム(2水
塩) 2.0g
エチレンジアミンテトラ酢酸鉄()アンモニウ
ム(2水塩) 120.0g
臭化カリウム 100.0g
水を加えて全量 1
定着液
水 800ml
チオ硫酸アンモニウム 80.0g
亜硫酸ナトリウム 5.0g
重亜硫酸ナトリウム 5.0g
水を加えて全量 1
安定浴
水 800ml
ホルマリン(37%) 5.0ml
富士ドライウエル 5.0ml
水を加えて全量 1.0[Table] From the above table, it can be seen that the samples of the present invention have low fogging and excellent storage stability. Example 2 Same as Example 1 except that a silver iodobromide emulsion containing 3 mol% of iodine (containing 100 g of silver halide and 70 g of gelatin per 1 kg of emulsion) was used instead of the emulsion used in Example 1. A coated sample containing the coupler and additives was prepared and subjected to the reversal treatment as described below. As in Example 1, the increase in fog when a phenidone compound was added to the S-separation type 2-equivalent magenta coupler was significantly reduced. It was found that this effect was effectively prevented without causing any discomfort. Processing process Temperature (℃) Time (minutes) 1 First development 38℃ 3 2 Water Washing 〃 1 3 Reversal 〃 2 4 Color development 〃 4 5 Adjustment 〃 2 6 Bleaching 38℃ 6 7 Fixing 〃 4 8 Water Washing 4 9 Stability 1 10 Drying The treated solution has the following composition. First developer water 800ml Sodium tetrapolyphosphate 2.0g Sodium bisulfite 8.0g Sodium sulfite 37.0g 1-phenyl-3-pyrazolidone 0.38g Hydroquinone 5.5g Sodium carbonate (monohydrate) 28.0g Potassium bromide 1.5g Potassium iodide 13.0mg Sodium thiocyanate 1.4g Add water to total volume 1 Reverse liquid water 800ml Hexasodium nitrilo-N・N・N-trimethylenephosphonate 3.0g Stannous chloride (dihydrate) 1.0g Sodium hydroxide 8.0g Ice Acetic acid 15.0ml Add water to make total volume 1.0 Color developer water 800ml Sodium tetrapolyphosphate 2.0g Benzyl alcohol 5.0ml Sodium sulfite 7.5g Sodium triphosphate (12 hydrate) 36.0g Potassium bromide 1.0g Potassium iodide 90.0mg Sodium hydroxide 3.0g Citrazic acid 1.5g 4-Amino-3-methyl-N-ethyl-β-hydroxyethylaniline sesquisulfate monohydrate 11.0g Ethylenediamine 3.0g Add water to make a total volume 1.0 Adjustment water 800ml Glacial acetic acid 5.0 ml Sodium hydroxide 3.0g Dimethylaminoethaneisothiourea (dihydrochloride)
1.0g Add water to total volume 1 Bleach solution water 800ml Sodium ethylenediaminetetraacetate (dihydrate) 2.0g Ethylenediaminetetraacetate iron () ammonium (dihydrate) 120.0g Potassium bromide 100.0g Add water to total volume 1 Fixing solution Water 800ml Ammonium thiosulfate 80.0g Sodium sulfite 5.0g Sodium bisulfite 5.0g Add water to total volume 1 Stable bath water 800ml Formalin (37%) 5.0ml Fuji Drywell 5.0ml Add water to total volume 1.0
Claims (1)
なくとも1種含有する乳剤層中及び/又は該乳剤
層に隣接する親水性コロイド層中に耐拡散性基を
有する1−フエニル−3−ピラゾリドン誘導体及
び一般式()で表わされるハイドロキノン誘導
体を写真用添加剤用高沸点有機溶媒の存在下で含
有させることを特徴とするカラー写真感光材料。 一般式() 式中R1はアニリノ基、アシルアミノ基又はウ
レイド基を表わし、R2はアラルキル基、アルキ
ル基又はアルケニル基を表わし、X1、X2、X3は
水素原子、アルキル基、ハロゲン原子、アルコキ
シ基、アリールオキシ基、アシルアミノ基、カル
バモイル基、スルフアモイル基、スルホニル基又
はシアノ基を表わし、X1、X2、X3は同一の基で
あつても異なる基であつてもよい。 一般式() 式中、Rは炭素数8〜30の置換もしくは無置換
アルキル基、置換もしくは無置換アリール基、ア
ルコキシ基、アリールオキシ基、カルバモイル
基、スルフアモイル基、アルコキシカルボニル基
又はアリールオキシカルボニル基を表わし、nは
1〜4の数を表わし、nが2以上のとき、各々の
Rは同じでも異なつていてもよい。[Scope of Claims] 1. A 1-phenyl compound having a diffusion-resistant group in an emulsion layer containing at least one coupler represented by the following general formula () and/or in a hydrophilic colloid layer adjacent to the emulsion layer. A color photographic material comprising a 3-pyrazolidone derivative and a hydroquinone derivative represented by the general formula () in the presence of a high-boiling organic solvent for use as a photographic additive. General formula () In the formula, R 1 represents an anilino group, an acylamino group, or a ureido group, R 2 represents an aralkyl group, an alkyl group, or an alkenyl group, and X 1 , X 2 , and X 3 represent a hydrogen atom, an alkyl group, a halogen atom, or an alkoxy group. , an aryloxy group, an acylamino group, a carbamoyl group, a sulfamoyl group, a sulfonyl group, or a cyano group, and X 1 , X 2 and X 3 may be the same group or different groups. General formula () In the formula, R represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, an alkoxy group, an aryloxy group, a carbamoyl group, a sulfamoyl group, an alkoxycarbonyl group, or an aryloxycarbonyl group having 8 to 30 carbon atoms, and n represents a number from 1 to 4, and when n is 2 or more, each R may be the same or different.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16316779A JPS5685748A (en) | 1979-12-14 | 1979-12-14 | Color photographic sensitive material |
US06/216,714 US4310623A (en) | 1979-12-14 | 1980-12-15 | Color photographic light-sensitive material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16316779A JPS5685748A (en) | 1979-12-14 | 1979-12-14 | Color photographic sensitive material |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5685748A JPS5685748A (en) | 1981-07-13 |
JPS6232780B2 true JPS6232780B2 (en) | 1987-07-16 |
Family
ID=15768501
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16316779A Granted JPS5685748A (en) | 1979-12-14 | 1979-12-14 | Color photographic sensitive material |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5685748A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0231678U (en) * | 1988-08-22 | 1990-02-28 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0667374A (en) * | 1992-08-18 | 1994-03-11 | Fuji Photo Film Co Ltd | Color image forming method |
US5484696A (en) * | 1994-12-22 | 1996-01-16 | Eastman Kodak Company | Photographic elements containing 2-equivalent pyrazolone magenta dye forming couplers and fade reducing compounds |
US5491054A (en) * | 1994-12-22 | 1996-02-13 | Eastman Kodak Company | Photographic elements containing 2-equivalent pyrazolone magenta dye forming couplers and stabilizing compounds |
-
1979
- 1979-12-14 JP JP16316779A patent/JPS5685748A/en active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0231678U (en) * | 1988-08-22 | 1990-02-28 |
Also Published As
Publication number | Publication date |
---|---|
JPS5685748A (en) | 1981-07-13 |
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