EP0887703B1 - Light-sensitive silver halide color photographic material - Google Patents
Light-sensitive silver halide color photographic material Download PDFInfo
- Publication number
- EP0887703B1 EP0887703B1 EP98111119A EP98111119A EP0887703B1 EP 0887703 B1 EP0887703 B1 EP 0887703B1 EP 98111119 A EP98111119 A EP 98111119A EP 98111119 A EP98111119 A EP 98111119A EP 0887703 B1 EP0887703 B1 EP 0887703B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- alkyl
- yellow dye
- dye forming
- couplers
- 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 - Lifetime
Links
- -1 silver halide Chemical class 0.000 title claims description 131
- 229910052709 silver Inorganic materials 0.000 title claims description 37
- 239000004332 silver Substances 0.000 title claims description 37
- 239000000463 material Substances 0.000 title claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 claims description 44
- 239000001043 yellow dye Substances 0.000 claims description 44
- 239000000839 emulsion Substances 0.000 claims description 38
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 238000005859 coupling reaction Methods 0.000 claims description 22
- 230000008878 coupling Effects 0.000 claims description 21
- 238000010168 coupling process Methods 0.000 claims description 21
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004442 acylamino group Chemical group 0.000 claims description 9
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 230000002209 hydrophobic effect Effects 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000005142 aryl oxy sulfonyl group Chemical group 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 239000010410 layer Substances 0.000 description 67
- 150000001875 compounds Chemical class 0.000 description 33
- 108010010803 Gelatin Proteins 0.000 description 22
- 229920000159 gelatin Polymers 0.000 description 22
- 239000008273 gelatin Substances 0.000 description 22
- 235000019322 gelatine Nutrition 0.000 description 22
- 235000011852 gelatine desserts Nutrition 0.000 description 22
- 239000000975 dye Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 13
- 230000035945 sensitivity Effects 0.000 description 11
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000011229 interlayer Substances 0.000 description 5
- 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 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000004848 polyfunctional curative Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 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
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- LOCAIGRSOJUCTB-UHFFFAOYSA-N indazol-3-one Chemical compound C1=CC=C2C(=O)N=NC2=C1 LOCAIGRSOJUCTB-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- MCSKRVKAXABJLX-UHFFFAOYSA-N pyrazolo[3,4-d]triazole Chemical compound N1=NN=C2N=NC=C21 MCSKRVKAXABJLX-UHFFFAOYSA-N 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- CWNSVVHTTQBGQB-UHFFFAOYSA-N N,N-Diethyldodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CC)CC CWNSVVHTTQBGQB-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- XCFIVNQHHFZRNR-UHFFFAOYSA-N [Ag].Cl[IH]Br Chemical compound [Ag].Cl[IH]Br XCFIVNQHHFZRNR-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005248 alkyl aryloxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- ZUIVNYGZFPOXFW-UHFFFAOYSA-N chembl1717603 Chemical compound N1=C(C)C=C(O)N2N=CN=C21 ZUIVNYGZFPOXFW-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
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- 230000001808 coupling effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 230000005764 inhibitory process Effects 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229940032007 methylethyl ketone Drugs 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
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- ZMUADARPXLFDHP-UHFFFAOYSA-N nitrocarbamic acid Chemical group OC(=O)N[N+]([O-])=O ZMUADARPXLFDHP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 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
- JPMVDVIGHJCZJW-UHFFFAOYSA-N octylsulfonylbenzene Chemical group CCCCCCCCS(=O)(=O)C1=CC=CC=C1 JPMVDVIGHJCZJW-UHFFFAOYSA-N 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/3225—Combination of couplers of different kinds, e.g. yellow and magenta couplers in a same layer or in different layers of the photographic material
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
- G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
- G03C7/30517—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution
- G03C7/30535—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution having the coupling site not in rings of cyclic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
- G03C7/30541—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the released group
- G03C7/30558—Heterocyclic group
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
- G03C7/30541—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the released group
-
- 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
Definitions
- the present invention refers to a light-sensitive silver halide color photographic multilayer material, in at least one blue light-sensitive layer associated with yellow dye forming couplers containing the combination of two different DIR (Development Inhibitor Releasing) couplers capable of releasing a development inhibiting compound upon reaction with the developing agent oxidation product.
- DIR Development Inhibitor Releasing
- Light-sensitive color photographic materials which make use of the substractive process for color reproduction, are known to comprise silver halide emulsion layers which are selectively sensitive to blue light, green light and red light and are associated with yellow dye, magenta dye and cyan dye forming couplers which (upon reaction with a primary amine type oxidized color developing agent) form complementary colors.
- an acylacetanilide type coupler is used to form a yellow colored image
- a pyrazolone, pyrazolotriazole, cyanacetophenone or indazolone type coupler is used to form a magenta colored image
- a phenolic, such as phenole or naphthole, type coupler is used to form a cyan colored image.
- a light-sensitive color photographic material in general comprises a blue-sensitive silver halide emulsion layer (or layers) which contains a yellow coupler and is mainly sensitive to blue light (substantially to wavelengths lower than about 500 nm), a green-sensitive silver halide emulsion layer (or layers) which contains a magenta coupler and is mainly sensitive to green light (substantially to wavelengths between about 500 and 600 nm) and a red- sensitive silver halide emulsion layer (or layers) which contains a cyan coupler and is mainly sensitive to red light (substantially to wavelengths higher than about 590 nm).
- DIR couplers which have a group with development inhibiting properties when it is released by the coupler itself. These groups are introduced into the coupling position of the coupler. Examples of DIR couplers are described by C.R. Barr, J.R. Thirtle and P.W. Wittum, Photographic Science and Eng., vol. 13, pp. 74-80 (1969) and ibid. pp.
- DIR couplers The purpose of DIR couplers is that of reducing granularity and improving image sharpness through intralayer or intraimage effects (i.e. within the same layer or the same colored image) and improving color reproduction through interlayer or interimage effects (i.e., within different layers or different colored images).
- intralayer or intraimage effects i.e. within the same layer or the same colored image
- interlayer or interimage effects i.e., within different layers or different colored images
- Patent application JP 51-113,625 describes the simultaneous use of mercapto type compounds which release the development inhibitor, such compounds having different coupling activities.
- Patent application JP 56-137,353 describes the simultaneous use of development inhibitor releasing compounds, one of which having a "timing" group and the other not having such "timing" group.
- DD patent 246,636 describes the use of a combination of two DIR compounds, the former defined as a movable compound and the latter as an unmovable one.
- US 4,355,100 describes the simultaneous use of two development inhibitor releasing compounds, the former having an amino group and the latter not having such amino group.
- US 5,126,236 describes the combination of DIR compounds or of DIR precursors or of compounds which release a DIR compound upon reaction with the oxidized developer agent.
- Patent application EP 747,763 describes a DIR yellow coupler of the type having a 1,2,4-triazolyl group attached to the coupling position, from which the 1,2,4-triazolyl group is released during development, such 1,2,4-triazolyl group comprising a hydrolizable alkoxy- or aryloxy-carbonyl group attached to a benzylthio substituent on the 1,2,4-triazolyl group.
- US 5,006,452 on the contrary describes a color photographic material containing a DIR coupler having a 4,7-dihalogen-2-benzotriazolyl type group which is released during development upon oxidation with a developer agent.
- US 5,332,656 describes a color photographic material containing the combination of a) a yellow dye forming diketomethylene coupler in its active coupling position having a 4,7-dihalogen-2-benzotriazolyl group which provides a compound having development inhibiting properties when the group is released from the active coupling position upon color development reaction, and b) a yellow dye forming alkoxybenzoyl-acetanilide coupler having a releasable 3-hydantoine group linked to the active coupling position.
- An object of the present invention is that of obtaining, for medium and low speed films, a higher inhibition action given by DIR couplers to obtain a reduced granularity, above all in low density regions where the granularity problems are more severe, and a higher color purity. It is another object of the present invention that of obtaining better interimage effects, but at the same time reducing to the minimum the sensitivity decrease in all layers.
- the present invention refers to a light-sensitive silver halide color photographic multilayer material which comprises a supporting base having coated thereon at least one blue light-sensitive silver halide emulsion layer, associated with yellow dye forming couplers, containing a) a yellow dye forming DIR coupler having a 1,2,4-triazolyl group attached to the coupling position thereof, from which the 1,2,4-triazolyl group is released during development, such 1,2,4-triazolyl group comprising a hydrolizable alkoxy- or aryloxy-carbonyl group attached to a benzylthio substituent on the 1,2,4-triazolyl group and b) a yellow dye forming malonodiamide DIR coupler having, in the coupling position thereof, a 4,7-dihalogen-2-benzotriazolyl group which gives a compound having development inhibiting properties when the group is released from the coupling position during development.
- Said light-sensitive silver halide color material containing the yellow- dye forming DIR coupler combination upon exposure and development, gives color images having a reduced granularity and a higher color purity, reducing to the minimum the speed decrease of all layers.
- Yellow dye forming DIR couplers having a 1,2,4-triazolyl group attached to the coupling position thereof, to be used in the present invention may be represented by the following formula (I): wherein
- the alkyl group represented by R 1 , R 2 and R 5 preferably has from 1 to 18 carbon atoms and may be substituted or unsubstituted.
- Preferred examples of alkyl group substituents comprise an alkoxy, aryloxy, cyano, amino, acylamino group, a halogen atom, a hydroxy, carboxy, sulfo, heterocyclic group, etc.
- alkyl groups are an iso-propyl, iso-butyl, tert.-butyl, iso-amyl, tert.-amyl, 1,1-dimethylbutyl, 1,1-dimethylhexyl, 1,1-diethylhexyl, 1,1-dimethyl-1-methoxyphenoxy-methyl, 1,1-dimethyl-1-ethylthiomethyl, dodecyl, hexadecyl, octadecyl, cyclohexyl, 2-methoxyisopropyl, 2-phenoxyisopropyl, ⁇ -aminoisopropyl, ⁇ -succinimidoisopropyl group.
- the aryl group represented with R 1 , R 2 and R 5 preferably has a total of from 6 to 35 carbon atoms and comprises in particular a substituted phenyl group and an unsubstituted phenyl group.
- substituents in the aryl group comprise a halogen atom, a nitro, cyano, thiocyano, hydroxy, alkoxy (preferably having from 1 to 15 carbon atoms, such as methoxy, isopropoxy, octyloxy, etc.), aryloxy (phenoxy, nitrophenoxy, etc.), alkyl (preferably having from 1 to 15 carbon atoms, such as methyl, ethyl, dodecyl, etc.), alkenyl (preferably having from 1 to 15 carbon atoms, such as allyl), aryl (preferably having from 6 to 10 carbon atoms, such as phenyl, tolyl, etc.), amino (for example an unsubstituted amino group or an alkyla
- TIME is a "timing" group which links the coupler residue with 1,2,4-triazolyl group and is released together with 1,2,4-triazolyl group during the coupling reaction with the oxidation product of a color developing agent and in its turn releases the 1,2,4-triazolyl group later on during development.
- timing groups represented with TIME in formula (I) comprise for examples the following groups: wherein Z is an oxygen or sulfur atom and is attached to the couplers, m is 0 or 1, R 8 is hydrogen or an alkyl with from 1 to 4 carbon atoms or an aryl group from 6 to 10 carbon atoms, X is hydrogen, halogen, cyano, nitro, alkyl with 1 to 20 carbon atoms, alkoxy, alkoxycarbonyl, acylamino, aminocarbonyl group, etc., as described in US 4,248,962, where the left portion is attached to the coupler and Z is oxygen or sulfur or R 9 , R 10 and R 11 each are hydrogen, alkyl or aryl groups and Q is a 1,2- or 1,4-phenylene or naphthylene group, as described in US 4,409,323.
- the alkyl group represented with R 3 and R 4 preferably is a lower 1 to 4 carbon atom alkyl group, such as methyl, ethyl, propyl, isopropyl, n-butyl and tert-butyl.
- DIR yellow dye forming couplers are represented by general formula (II): wherein R 3 and R 4 each represent a substituent as defined for formula (I), TIME and n are as defined for formula (I), R 6 represents an alkyl or an aryl group, R 7 is a halogen atom, an alkyl group (having from 1 to 20 carbon atoms) or an aryl group (with from 6 to 10 carbon atoms) and Ball is a hydrophobic ballasting group.
- the alkyl group represented with R 6 preferably has from 3 to 8 carbon atoms and more preferably is a branched-chain alkyl group (such as for instance an iso-propyl, tert-butyl or tert-amyl group) and the aryl group represented with R 6 preferably is a phenyl group which may be substituted with a alkyl or alkoxy group having from 1 to 5 carbon atoms (for instance a 2- or 4-alkylphenyl group such as a 2-methylphenyl, or a 2- or 4-alkoxyphenyl group, such as 2-methoxyphenyl, 4-isopropoxyphenyl or 2-butoxyphenyl).
- R 7 represents a halogen atom (such as chlorine) or an alkyl or alkoxy group having from 1 to 4 carbon atoms (such as methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, propoxy, iso-propoxy, n-butoxy and tert-butoxy).
- halogen atom such as chlorine
- R 7 represents a halogen atom (such as chlorine) or an alkyl or alkoxy group having from 1 to 4 carbon atoms (such as methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, propoxy, iso-propoxy, n-butoxy and tert-butoxy).
- ballasting group is a ballasting group, for example an organic group of such sizes and shape as to make the group to which it is attached non-diffusing from the layer where it is coated in a photographic material.
- ballasting group comprises a hydrophobic organic residue having from 8 to 32 carbon atoms linked to the coupler directly or through a divalent linking group, such as for instance an alkylene, imino, ether, thioether, carbonamido, sulfonamido, ureido, ester, imido, carbamoyl and sulfamoyl group.
- ballasting groups comprise (linear, branched or cyclic) alkyl, alkenyl, alkoxy, alkylaryl, alkylaryloxy, alkylamidoalkyl, alkoxyalkyl, alkoxyaryl groups, or alkyl groups substituted with an aryl or a heterocyclic group, aryl groups substituted with an aryloxyalkoxycarbonyl group and residues containing both an alkenyl and a long alkenyl chain aliphatic group and a carboxy group or a water-soluble sulfo group, as described for example in US 3,337,344; 3,418,129; 4,138,258 and 4,451,559 and in GB 1,494,777.
- R 3 and R 4 each represents a substituent as defined in formula (I); TIME and n are as defined in formula (I);
- R 12 represents a branched-chain alkyl group, preferably having from 3 to 8 carbon atoms (such as for example an isopropyl, isobutyl, tert-butyl or tert-amyl group);
- R 13 represents an alkyl group preferably having from 8 to 22 carbon atoms (such as for instance a dodecyl, tetradecyl, hexadecyl or octadecyl group), a phenoxyalkyl group, preferably having from 10 to 32 carbon atoms (such as for instance a ⁇ -(2,4-ditert-amylphenoxypropyl), an alkoxyphenyl group, preferably having from 10 to 32 carbon atoms or an aralkyl group
- alkyl group includes not only such alkyl unit, like methyl, ethyl, butyl, octyl, stearyl, etc., but even those units bearing substituent groups such as halogen, cyano, hydroxyl, nitro, amino, carboxylate, etc.
- alkyl unit comprises only methyl, ethyl, stearyl, cyclohexyl, etc.
- the yellow dye forming DIR couplers having a 1,2,4-triazolyl group attached to the coupling position thereof to be used in the present invention can be prepared according to the conventional procedures for the preparation of DIR couplers, see for instance EP patent application 747,763.
- Yellow dye forming malonodiamide DIR couplers of the present invention are characterized by having a 4,7-dihalogen-2-benzotriazolyl group attached to the active methylene group (active coupling position) of the yellow dye forming coupler through the nitrogen atom in the 2-position of such group, the remaining 5 and 6 positions of such group being substituted or not substituted.
- Yellow dye forming malonodiamide DIR couplers of the present invention may be represented by formula (IV): wherein R 14 and R 15 , the same or different, each represent a halogen atom (chlorine, bromine, iodine and fluorine) and R 16 and R 17 , the same or different, each represent a hydrogen atom, a halogen atom (chlorine, bromine, iodine and fluorine), an amino group, an alkyl group having from 1 to 4 carbon atoms (methyl, ethyl, butyl, chloromethyl, trifluoromethyl, 2-hydroxyethyl, etc.), an alkoxy group having from 1 to 4 carbon atoms (methoxy, chloromethoxy, ethoxy, butoxy, etc.), a hydroxy group, a cyano group, an aryloxy group (phenoxy, p-methoxyphenoxy, etc.), an acyloxy group (acyloxy, benzoyloxy, etc.
- the alkyl group represented with R 18 and R 19 preferably has from 1 to 18 carbon atoms and may be substituted or non substituted.
- Preferred examples of the alkyl group substituents comprise an alkoxy, aryloxy, cyano, amino, acylamino group, a halogen atom, a hydroxy, carboxy, sulfo, heterocyclic group, etc.
- alkyl groups are an iso-propyl, an iso-butyl, a tert.-butyl, an iso-amyl, a tert.-amyl, a 1,1-dimethylbutyl, a 1,1-dimethylhexyl, a 1,1-diethylhexyl, a 1,1-dimethyl-1-methoxyphenoxymethyl, a 1,1-dimethyl-1-ethylthiomethyl, a dodecyl, a hexadecyl, an octadecyl, a cyclohexyl, a 2-methoxyisopropyl, a 2-phenoxyisopropyl, an ⁇ -aminoisopropyl, an ⁇ -succinimidoisopropyl group, etc.
- the yellow dye forming malonodiamide DIR couplers according to the present invention may be represented with formula (V): wherein R 16 and R 17 are the same as defined in formula (IV); R 20 and R 21 each represent a hydrogen or a halogen atom (chlorine, bromine, iodine and fluorine); R 22 and R 23 each represent a halogen atom, a nitro, cyano, thiocyano, hydroxy, alkoxy (preferably having from 1 to 15 carbon atoms, such as methoxy, isopropoxy, octyloxy, etc.), aryloxy (preferably having up to 20 carbon atoms, such as phenoxy, nitrophenoxy, etc.), alkyl (preferably having from 1 to 15 carbon atoms, such as methyl, ethyl, dodecyl, etc.), alkenyl (preferably having from 1 to 15 carbon atoms, such as allyl), aryl (preferably having up to 10 carbon atoms,
- the total number of carbon atoms made up by R 22 and R 23 preferably is comprised between 6 and 35.
- the yellow dye forming malonodiamide DIR couplers according to the present invention may be represented with formula (VI): wherein R 24 and R 25 each represent an alkyl group having from 1 to 20 carbon atoms (such as methyl, ethyl, dodecyl, etc.) and R 26 and R 27 each represent a low alkyl group having from 1 to 4 carbon atoms (such as methyl, ethyl, butyl, etc.).
- the yellow dye forming malonodiamide DIR couplers to be used in the present invention can be synthesized by following methods which are known from the DIR coupler synthesis, as described in US 5,006,452.
- the yellow dye forming malonodiamide DIR couplers to be used in the present invention may be hydrophilic couplers (Fischer type couplers) having a water solubilizing group, for instance a carboxy, hydroxy, sulfo group, etc., or hydrophobic couplers.
- the methods for adding the couplers to a hydrophilic colloidal solution or to a silver halide gelatin photographic emulsion or dispersing therein said couplers may be the conventional ones known in the art, such as for instance the solid dispersion method, the latex dispersion method and, preferably, the oil dispersion method.
- the hydrophobic couplers of the present invention can be dissolved in a water insoluble high-boiling solvent and the resulting solution can be emulsified in a water medium as described for instance in US 2,304,939; 2,322,027, etc., or said hydrophobic couplers are dissolved in said water insoluble high boiling organic solvent in combination with low-boiling organic solvents and the resulting solution can be emulsified in the water medium as described for instance in US 2,801,170; 2,801,171; 2,949,360, etc.
- Typical high-boiling known solvents comprise phthalic acid esters (e.g.
- Typical low-boiling known solvents include ethylacetate, butylacetate, methylethylketone, cyclohexanone, 2-ethoxyethylacetate, dimethylformamide, etc. Specific examples of the latex dispersion method are described in US 4,199,363.
- the DIR couplers to be used in the present invention are preferably incorporated into silver halide emulsion layers. Preferably, they are incorporated into blue-sensitive or sensitized silver halide emulsions layers, associated with yellow dye forming couplers. More preferably, the yellow dye forming DIR couplers having a 1,2,4-triazolyl group attached to the coupling position to be used in the present invention and the yellow dye forming malonodiamide DIR couplers used in the present invention are both incorporated into blue high sensitive silver halide emulsion layers.
- the quantity of yellow dye forming DIR couplers, having a 1,2,4-triazolyl group attached to the coupling position, to be incorporated ranges from about 0.010 to about 0.100 grams per square meter, preferably from about 0.020 to about 0.040 grams per square meter of the color photographic element, in a weight ratio with respect to the silver halide present in the blue-sensitive high sensitivity layer from about 0.045 to about 0.090.
- the quantity of the yellow dye forming malonodiamide DIR couplers to be incorporated ranges from about 0.005 to about 0.040 grams per square meter, preferably from 0.010 to 0.030 grams per square meter of the color photographic element, in a weight ratio with respect to the silver halide quantity present in the blue-sensitive high-sensitivity layer from about 0.020 to about 0.050.
- the photographic elements of the present invention are preferably color multilayer elements comprising a blue-sensitive or sensitized silver halide layer associated with yellow dye forming color couplers, a green sensitized silver halide layer associated with magenta dye forming color couplers and a red sensitized silver halide emulsion layer associated with cyan dye forming color couplers.
- Each layer may consist of a single emulsion layer or of multiple emulsion sub-layers sensitive to a given region of the visible spectrum. If the multilayer materials contain blue, green or red sensitive multiple sub-layers, there may be relatively more sensitive or less sensitive sub-layers.
- the photographic elements may contain additional layers, such as filtering layers, interlayers, protective layers, sublayers, and the like.
- Coupler is positioned in such a relationship with the silver halide emulsion that the coupler and the layer are capable of interacting to give rise to an image-wise correspondence between the silver image formed upon development and the colored image formed by the coupler. This is achieved by positioning the coupler either into the silver halide emulsion layer or into a colloidal layer adjacent thereto which may be light insensitive.
- Preferred couplers to be used in the present invention comprise those which are not diffusing due to the presence of a hydrophobic ballasting group in their molecule.
- cyan dye forming couplers are the conventional phenolic and ⁇ -naphtholic compounds.
- Examples of cyan couplers may be selected among those described in US 2,369,929; 2,474,293; 2,895,826; 3,311,476; 3,253,924; 3,419,390; 3,458,315; 3,476,563 and 3,591,383; in GB 1,201,110 and in Research Disclosure 308119, VII, 1989.
- magenta dye forming couplers are the conventional pyrazolone type or indazolone, cyanoacetyl, pyrazolotriazole type compounds, etc.; particularly preferred compounds are the pyrazolone type couplers.
- Magenta dye forming couplers are described for instance in US 2,600,788; 2,983,608; 3,062,653; 3,127,269; 3,311,476; 3,419,391; 3,519,429; 3,558,319; 3,582,322; 3,615,506; 3,834,908 and 3,891,445 and in Research Disclosure 308119, VII, 1989.
- the silver halide emulsion used in the present invention may be a silver chloride, silver bromide, silver chlorobromide, silver iodobromide and silver chloroiodobromide fine dispersion in a hydrophilic binder.
- the hydrophilic binder may any hydrophilic polymer selected among those conventionally used in photography, comprising gelatin, a gelatin derivative, such as acylated gelatin, graft gelatin, etc., albumin, gum arabic, agar agar, a cellulose derivative, such as hydroxyethylcellulose, carboxymethylcellulose, etc., a synthetic resin, such as polyvinylalcohol, polyvinylpyrrolidone, polyacrylamide, etc.
- Preferred silver halides are silver iodobromide or silver iodobromochloride containing from 1 to 20% iodide moles.
- the silver halide grains may have any crystal shape, such as a cubical, octahedrical, tabular shape or a mixed crystal shape.
- the silver halide may have uniform grain sizes or a broader size distribution.
- the silver halide sizes may range from about 0.1 to about 5 mm.
- the silver halide emulsion may be prepared by using a single jet, a double jet method or a combination of these methods or may be ripened using for instance an ammonia, a neutralization, an acid method, etc.
- the emulsions which are used in the present invention may be chemically and optically sensitized as described in Research Disclosure 17643, III and IV, December 1978 and in Research Disclosure 308119, III, 1989. They may contain optical brighteners, antifogging agents and stabilizers, filtering and antihalo dyes, masked dyes, development accelerator releasing couplers, hardeners, coating adjuvants, plasticizers and lubricants and other auxiliary substances, such for instance described in Research Disclosure 17643, V, VI, VIII, X, XI and XII, December 1978 and in Research Disclosure 308119, V, VI, VIII, X, XI and XII, 1989.
- the photographic emulsion layers and the photographic element layers may contain various colloids, alone or in combination, such as binders, as described for instance in Research Disclosure 17643, IX, December 1978.
- the above described emulsions may be coated onto various support bases (cellulose triacetate, paper, resin-coated paper, polyesters, such as for example polyethylene terephthalate or polyethylene naphthalate support bases) by adopting various methods, as described in Research Disclosure 17643, XV and XVII, December 1978 and in Research Disclosure 308119, XVII, 1989.
- the light-sensitive silver halides contained in the photographic elements of the present invention after exposure, may be processed to form a visible image by associating the silver halide to an alkaline water medium in the presence of a developer agent contained in the water medium or in the element.
- Formulations and techniques are described in Research Disclosure 17643, XIX, XX and XXI, December 1978 and in Research Disclosure 308119, XIX and XX, 1989.
- a multilayer color photographic element (Sample 101, comparison example) was prepared by coating layers of the hereinafter reported composition onto a transparent cellulose acetate film support provided with a gelatin underlayer.
- the coating quantity of silver halides (expressed as silver-equivalent), gelatin and other additions are reported in grams per square meter (g/m 2 ). All silver halide emulsions were stabilized with 4-hydroxy-6-methyl-1,3,3a,7-tetrazaindene and spectrally sensitized with suitable sensitizing dyes for the red, green and blue light of the spectrum.
- Comparison Sample 101 did not give good sensitometrical results.
- Comparison Sample 101 containing Compound I-1 but not Compound II-1, showed good speed values, but a too high and unacceptable granularity.
- Comparison Sample 102 containing Compound II-1, but not Compound I-1 , showed a good granularity, but too low and unacceptable speed values.
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- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI971504 | 1997-06-26 | ||
| IT97MI001504A IT1292202B1 (it) | 1997-06-26 | 1997-06-26 | Materiale fotografico fotosensibile a colori agli alogenuri d'argento |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0887703A1 EP0887703A1 (en) | 1998-12-30 |
| EP0887703B1 true EP0887703B1 (en) | 2001-08-22 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP98111119A Expired - Lifetime EP0887703B1 (en) | 1997-06-26 | 1998-06-17 | Light-sensitive silver halide color photographic material |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0887703B1 (ja) |
| JP (1) | JPH1124215A (ja) |
| DE (1) | DE69801402T2 (ja) |
| IT (1) | IT1292202B1 (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69920665T2 (de) * | 1999-05-25 | 2005-10-06 | Ferrania S.P.A., Cairo Montenotte | Farbphotographische lichtempfindliche Silberhalogenidelemente mit verbesserter Bildqualität |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3712446A1 (de) * | 1987-04-11 | 1988-10-20 | Agfa Gevaert Ag | Farbfotografisches aufzeichnungsmaterial mit einem gelb-dir-kuppler |
| IT1223507B (it) * | 1987-12-17 | 1990-09-19 | Minnesota Mining & Mfg | Materiale fotografico fotosensibile a colori agli alogenuri d'argento |
| DE69116907T2 (de) * | 1990-03-12 | 1996-10-17 | Fuji Photo Film Co Ltd | Farbphotographisches Silberhalogenidmaterial |
| IT1256017B (it) * | 1992-04-07 | 1995-11-20 | Minnesota Mining & Mfg | Materiale fotografico a colori agli alogenuri d'argento sensibile alla luce |
| DE69512768T2 (de) * | 1995-06-06 | 2000-06-29 | Tulalip Consultoria Comercial | Farbphotographische lichtempfindliche silberhalogenid Elemente mit verbesserter Bildqalität |
-
1997
- 1997-06-26 IT IT97MI001504A patent/IT1292202B1/it active IP Right Grant
-
1998
- 1998-06-11 JP JP10163426A patent/JPH1124215A/ja active Pending
- 1998-06-17 DE DE69801402T patent/DE69801402T2/de not_active Expired - Fee Related
- 1998-06-17 EP EP98111119A patent/EP0887703B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH1124215A (ja) | 1999-01-29 |
| ITMI971504A1 (it) | 1998-12-26 |
| DE69801402T2 (de) | 2002-06-06 |
| IT1292202B1 (it) | 1999-01-25 |
| ITMI971504A0 (ja) | 1997-06-26 |
| DE69801402D1 (de) | 2001-09-27 |
| EP0887703A1 (en) | 1998-12-30 |
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