EP0871066B1 - Colour photographic silver halide material - Google Patents
Colour photographic silver halide material Download PDFInfo
- Publication number
- EP0871066B1 EP0871066B1 EP98105593A EP98105593A EP0871066B1 EP 0871066 B1 EP0871066 B1 EP 0871066B1 EP 98105593 A EP98105593 A EP 98105593A EP 98105593 A EP98105593 A EP 98105593A EP 0871066 B1 EP0871066 B1 EP 0871066B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- silver halide
- layer
- colour photographic
- photographic silver
- sensitive
- 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 39
- 229910052709 silver Inorganic materials 0.000 title claims description 36
- 239000004332 silver Substances 0.000 title claims description 36
- 239000000463 material Substances 0.000 title claims description 28
- 239000000839 emulsion Substances 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- ZEUDGVUWMXAXEF-UHFFFAOYSA-L bromo(chloro)silver Chemical compound Cl[Ag]Br ZEUDGVUWMXAXEF-UHFFFAOYSA-L 0.000 claims description 4
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- MCSKRVKAXABJLX-UHFFFAOYSA-N pyrazolo[3,4-d]triazole Chemical group N1=NN=C2N=NC=C21 MCSKRVKAXABJLX-UHFFFAOYSA-N 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 90
- 108010010803 Gelatin Proteins 0.000 description 25
- 229920000159 gelatin Polymers 0.000 description 25
- 239000008273 gelatin Substances 0.000 description 25
- 235000019322 gelatine Nutrition 0.000 description 25
- 235000011852 gelatine desserts Nutrition 0.000 description 25
- 238000011160 research Methods 0.000 description 17
- 239000010408 film Substances 0.000 description 12
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 11
- 239000000975 dye Substances 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 239000006096 absorbing agent Substances 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- 101710134784 Agnoprotein Proteins 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000011241 protective layer Substances 0.000 description 6
- IEIREBQISNYNTN-UHFFFAOYSA-K [Ag](I)(Br)Cl Chemical compound [Ag](I)(Br)Cl IEIREBQISNYNTN-UHFFFAOYSA-K 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 206010070834 Sensitisation Diseases 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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 1
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 1
- INVVMIXYILXINW-UHFFFAOYSA-N 5-methyl-1h-[1,2,4]triazolo[1,5-a]pyrimidin-7-one Chemical compound CC1=CC(=O)N2NC=NC2=N1 INVVMIXYILXINW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 101100493713 Caenorhabditis elegans bath-45 gene Proteins 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241001295925 Gegenes Species 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 108091002531 OF-1 protein Proteins 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- UMEAURNTRYCPNR-UHFFFAOYSA-N azane;iron(2+) Chemical compound N.[Fe+2] UMEAURNTRYCPNR-UHFFFAOYSA-N 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- OIPQUBBCOVJSNS-UHFFFAOYSA-L bromo(iodo)silver Chemical compound Br[Ag]I OIPQUBBCOVJSNS-UHFFFAOYSA-L 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 229940100539 dibutyl adipate Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- GSACTQIQWJFGIK-UHFFFAOYSA-N n-[2-(n-ethyl-2-methylanilino)ethyl]methanesulfonamide;sulfuric acid Chemical compound OS(O)(=O)=O.CS(=O)(=O)NCCN(CC)C1=CC=CC=C1C GSACTQIQWJFGIK-UHFFFAOYSA-N 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
- G03C7/3882—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific polymer or latex
-
- 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
- G03C7/392—Additives
- G03C7/39208—Organic compounds
- G03C7/3924—Heterocyclic
- G03C7/39268—Heterocyclic the nucleus containing only oxygen as hetero atoms
-
- 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
- G03C7/392—Additives
- G03C7/396—Macromolecular additives
Definitions
- the invention relates to a color photographic silver halide material with improved Characteristics.
- So-called white couplers or redox-active are used to solve these tasks Connections used. These are usually pyrazolone couplers with a methyl group in the coupling site or around diffusion-resistant Hydroquinones, disulfonamidophenols and N-aryl-N'-acylhydrazine. These connections but can meet the requirements of practice as described above are not sufficiently fulfilled.
- Acyl residues R 1 can be residues of an aromatic or aliphatic carboxylic, carbamic, carbonic, sulfonic, sulfinic or phosphoric acid.
- the incorporation into a polymer chain can take place via an unsaturated group, for example a styrene, acrylic acid or methacrylic acid group.
- unsaturated group for example a styrene, acrylic acid or methacrylic acid group.
- a suitable monomer is, for example
- the compound of formula I can be made to a polymer via a polymer-analogous reaction.
- a polymer-analogous reaction For example, the following connection be bound to a polymer:
- R 2 is R 3 and n is m.
- R 1 is preferably hydrogen or acyl
- R 2 and R 3 are alkyl, the sum of the C atoms in the alkyl radicals R 2 and R 3 being 8 8.
- Preferred acyl residues are the residues of aromatic and aliphatic carboxylic acids.
- the position of the substituents relates to the oxygen.
- the position is 3 para-constant to the 2nd ring link.
- the other compounds mentioned are obtained in a corresponding manner. If the reactivity of the phenolic component is reduced, it can be aggravated Reaction conditions become necessary e.g. by increasing the temperature, Increasing the concentration of sulfuric acid in the melt etc. Furthermore, all or part of the sulfuric acid can be replaced by other acids e.g. by p-toluenesulfonic acid, methanesulfonic acid, phosphoric acid, polyphosphoric acid, Phthalic acid, trifluoroacetic acid, boric acid and the like. like.
- the compounds of formula (I) are preferably used in an amount of 5 to 1000 mg / m 2 , in particular 10 to 500 mg / m 2 .
- the compounds of formula (I) can also be present as a salt (phenolate); as Cations are particularly suitable for metal cations and ammonium ions Alkali metal ions and trialkyl or tetraalkylammonium ions.
- color photographic materials are color negative films, color reversal films, Color positive films, color photographic paper, color reversal photographic paper, color-sensitive materials for the color diffusion transfer process or the silver color bleaching process.
- the photographic materials consist of a support on which at least one photosensitive silver halide emulsion layer is applied.
- Suitable as a carrier especially thin films and foils.
- the color photographic materials usually contain at least one red-sensitive, green sensitive and blue sensitive silver halide emulsion layer and optionally intermediate layers and protective layers.
- these layers can vary be arranged. This is shown for the most important products:
- Color photographic films such as color negative films and color reversal films show in in the following order on the carrier 2 or 3 red-sensitive, cyan-coupling silver halide emulsion layers, 2 or 3 green-sensitive, purple-coupling silver halide emulsion layers and 2 or 3 blue-sensitive, yellow-coupling silver halide emulsion layers.
- the layers same spectral sensitivity differ in their photographic sensitivity, with the less sensitive sub-layers usually closer arranged to the carrier than the higher sensitive sub-layers.
- a yellow filter layer is applied, which prevents blue light from entering the to get layers below.
- Color photographic paper which is usually much less sensitive to light as a color photographic film, points in the order given below usually a blue-sensitive, yellow-coupling silver halide emulsion layer on the support, a green sensitive, purple coupling silver halide emulsion layer and a red sensitive, cyan-coupling silver halide emulsion layer on; the yellow filter layer can be omitted.
- Deviations in the number and arrangement of the photosensitive layers can occur to achieve certain results. For example, you can all highly sensitive layers in one layer package and all low-sensitive layers Layers to another layer package in a photographic film be summarized to increase sensitivity (DE-25 30 645).
- Essential components of the photographic emulsion layers are binders, Silver halide grains and color couplers.
- Photographic materials with camera sensitivity usually contain silver bromide iodide or silver bromide iodide chloride emulsions.
- Photographic copy materials contain either silver chloride bromide emulsions with up to 80 mol% AgBr or silver chloride bromide emulsions with over 95 mol% AgCl.
- the maximum absorption of that from the couplers and the color developer oxidation product Dyes formed are preferably in the following areas: Yellow coupler 430 to 460 nm, purple coupler 540 to 560 nm, cyan coupler 630 up to 700 nm.
- hydrophobic color couplers but also other hydrophobic components of the layers, are usually in high-boiling organic solvents dissolved or dispersed. These solutions or dispersions are then in one emulsified aqueous binder solution (usually gelatin solution) and lie after drying the layers as fine droplets (0.05 to 0.8 ⁇ m diameter) in the layers before.
- aqueous binder solution usually gelatin solution
- the usually between layers of different spectral sensitivity arranged non-light-sensitive intermediate layers can contain agents which an undesirable diffusion of developer oxidation products from a photosensitive to another photosensitive layer with different prevent spectral sensitization.
- Suitable connections can be found in Research Disclosure 37254, Part 7 (1995), p. 292 and in Research Disclosure 37038, Part III (1995), p. 84.
- the photographic material can also contain UV light-absorbing compounds, white toners, spacers, filter dyes, formalin scavengers, light stabilizers, antioxidants, D min dyes, additives to improve the stability of dyes, couplers and whites and to reduce the color fog, plasticizers (latices), Contain biocides and others.
- Suitable compounds can be found in Research Disclosure 37254, Part 8 (1995), P. 292 and in Research Disclosure 37038, parts IV, V, VI, VII, X, XI and XIII (1995), p. 84 ff.
- the layers of color photographic materials are usually hardened, i.e. the binder used, preferably gelatin, is by suitable cross-linked chemical processes.
- Suitable hardener substances can be found in Research Disclosure 37254, Part 9 (1995), p. 294 and in Research Disclosure 37038, Part XII (1995), page 86.
- the compounds of formula (I) are in particular in at least one neighboring layer to a green sensitive, containing at least one purple coupler Silver halide emulsion layer used, the silver halide emulsion is a silver bromide chloride emulsion with at least 95 mol% AgCl.
- a color photographic recording material was produced by applying the following layers in the order given to a support made of paper coated on both sides with polyethylene. The quantities given relate to 1 m 2 . The corresponding amounts of AgNO 3 are given for the silver halide application.
- Samples 2 to 14 are prepared like sample 1 with the difference that in layers 2, 3, 4 and 5 the compounds Y-1, SC-1, SC-2 and M-1 are replaced by those given in table 1 , In addition, the silver coating in layer 4 was reduced to 0.28 g for samples 4 to 9 and to 0.22 g for samples 10 to 14. (V: comparison, E: according to the invention) [amount in mg / m 2 ] Sample No.
- a color photographic recording material for color negative development was produced (sample 15 - comparison) by applying the following layers in the order given to a transparent layer support made of cellulose triacetate with a thickness of 120 ⁇ m and having an adhesive layer. The amounts are given in g / m 2 . The corresponding amounts of AgNO 3 are given for the silver halide application. All silver halide emulsions per 100 g of AgNO 3 were stabilized with 0.1 g of 4-hydroxy-6-methyl-1,3,3a, 7-tetraazaindene. The silver halide emulsions are characterized by the halide composition and in terms of grain size by the center of gravity (VSP).
- VSP center of gravity
- red-sensitized silver bromoiodide emulsion (10.0 mol% iodide; VSP 0.56) 1.2 gelatin 0.9 Teal Coupler C-2 0.2 colored coupler CR-1 7.0 x 10 -2 colored coupler CY-1 3.0 x 10 -2 DIR coupler DIR-1 4.0 x 10 -2
- red-sensitized silver bromoiodide emulsion (6.8 mol% iodide; VSP 1.2) 1.6 gelatin 1.2 Teal coupler C-3 0.15 DIR coupler DIR-3 3.0 x 10 -2
- the colorless and colored couplers were used together with the same Amount of tricresyl phosphate (CPM) according to the emulsification methods known in the art brought in.
- CPM tricresyl phosphate
- Samples 16 to 18 differ from sample 15 in that they additionally contain compounds of the formula (I) (g / m 2 ) in layer 1.
- the samples were then exposed to daylight behind a graduated gray wedge.
- the materials were then processed according to the process described in E. Ch. Gehret, The British J. of Photography 1974, p. 597.
- the relative red sensitivity and the bluish-green haze were measured from the samples obtained.
- the results are shown in Table 3.
- Samples 19 to 24 differ from sample 15 in that an additional 0.125 mmol of the compounds listed in table 4 / m 2 were used in layer 5. Samples 23 and 24 instead contained white couplers W-1 and W-2 in an amount of 0.125 mmol / m 2 .
- White coupler W 2 has the formula:
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Description
Die Erfindung betrifft ein farbfotografisches Silberhalogenidmaterial mit verbesserten Eigenschaften.The invention relates to a color photographic silver halide material with improved Characteristics.
Die Anforderungen der Praxis an EOP-Fänger (Abfangreagenzien für das Entwickleroxidationsprodukt)
in farbfotografischen Silberhalogenidmaterialien (Colorfilm
und Colorpapier) sind
Zur Lösung dieser Aufgaben werden sogenannte Weißkuppler oder redoxaktive Verbindungen eingesetzt. Dabei handelt es sich üblicherweise um Pyrazolonkuppler mit einer Methylgruppe in der Kupplungsstelle bzw. um diffusionsfeste Hydrochinone, Disulfonamidophenole und N-Aryl-N'-acylhydrazine. Diese Verbindungen können aber die Anforderungen der Praxis, wie sie vorstehend beschrieben sind, nicht ausreichend erfüllen.So-called white couplers or redox-active are used to solve these tasks Connections used. These are usually pyrazolone couplers with a methyl group in the coupling site or around diffusion-resistant Hydroquinones, disulfonamidophenols and N-aryl-N'-acylhydrazine. These connections but can meet the requirements of practice as described above are not sufficiently fulfilled.
Es wurde nun gefunden, daß sich mit bestimmten Benzofuranonen überraschende Verbesserungen erzielen lassen.It has now been found that certain benzofuranones are surprising Make improvements.
Gegenstand der Erfindung ist daher ein farbfotografisches Sillberhalogenidmaterial
mit einem Träger und wenigstens einer lichtempfindlichen Silberhalogenidemulsionsschicht,
das in wenigstens einer Schicht wenigstens eine Verbindung der allgemeinen
Formel (I) enthält:
worin
- R1
- Wasserstoff, Alkyl oder Acyl,
- R2, R3
- unabhängig voneinander Alkyl, Cycloalkyl, Alkenyl, Aryl, Halogen, OR4, SR5, NR6R7, Nitro, Cyano, SO2R8, COOR9, COR10 oder Hetaryl,
- R4, R5, R9
- unabhängig voneinander Alkyl, Cycloalkyl, Alkenyl, Aryl oder Hetaryl,
- R6, R7
- unabhängig voneinander H, R4, COR10, COOR9, SO2R8,
- R8, R10
- unabhängig voneinander Alkyl, Cycloalkyl, Alkenyl, Aryl, Hetaryl oder NR6R7,
- n, m 0, 1, 2, 3 oder 4
- bedeuten oder 2 Reste R2 bzw. R3 jeweils einen ankondensierten carbo- oder heterocyclischen Ring bedeuten können oder die Verbindung der Formel I über einen der Reste R1, R2 oder R3 an eine Polymerkette gebunden ist. Bevorzugt befindet sich mindestens einer der Reste R2 und R3 in para-Stellung zum phenolischen Sauerstoff.
which contains at least one compound of the general formula (I) in at least one layer: wherein
- R 1
- Hydrogen, alkyl or acyl,
- R 2 , R 3
- independently of one another alkyl, cycloalkyl, alkenyl, aryl, halogen, OR 4 , SR 5 , NR 6 R 7 , nitro, cyano, SO 2 R 8 , COOR 9 , COR 10 or hetaryl,
- R 4 , R 5 , R 9
- independently of one another alkyl, cycloalkyl, alkenyl, aryl or hetaryl,
- R 6 , R 7
- independently of one another H, R 4 , COR 10 , COOR 9 , SO 2 R 8 ,
- R 8 , R 10
- independently of one another alkyl, cycloalkyl, alkenyl, aryl, hetaryl or NR 6 R 7 ,
- n, m 0, 1, 2, 3 or 4
- mean or 2 radicals R 2 or R 3 can each mean a fused-on carbo- or heterocyclic ring or the compound of formula I is bound to a polymer chain via one of the radicals R 1 , R 2 or R 3 . At least one of the radicals R 2 and R 3 is preferably para to the phenolic oxygen.
Acylreste R1 können Reste einer aromatischen oder aliphatischen Carbon-, Carbamin-, Kohlen,- Sulfon-, Sulfin- oder Phosphorsäure sein.Acyl residues R 1 can be residues of an aromatic or aliphatic carboxylic, carbamic, carbonic, sulfonic, sulfinic or phosphoric acid.
Der Einbau in eine Polymerkette kann über eine ungesättigte Gruppe erfolgen, beispielsweise eine Styrol-, Acrylsäure- oder Methacrylsäuregruppe. Ein geeignetes Monomer ist beispielsweise The incorporation into a polymer chain can take place via an unsaturated group, for example a styrene, acrylic acid or methacrylic acid group. A suitable monomer is, for example
Weiterhin kann die Verbindung der Formel I an ein Polymer über eine polymeranaloge Reaktion erfolgen. Z.B. kann die folgende Verbindung an ein Polymer gebunden werden: Furthermore, the compound of formula I can be made to a polymer via a polymer-analogous reaction. For example, the following connection be bound to a polymer:
In einer bevorzugten Ausführungsform ist R2 gleich R3 und n gleich m.In a preferred embodiment, R 2 is R 3 and n is m.
Bevorzugt bedeuten R1 Wasserstoff oder Acyl, R2 und R3 Alkyl, wobei die Summe der C-Atome in den Alkylresten R2 und R3 ≥ 8 ist. Bevorzugte Acylreste sind die Reste aromatischer und aliphatischer Carbonsäuren.R 1 is preferably hydrogen or acyl, R 2 and R 3 are alkyl, the sum of the C atoms in the alkyl radicals R 2 and R 3 being 8 8. Preferred acyl residues are the residues of aromatic and aliphatic carboxylic acids.
Beispiele für Verbindungen der Formel (I), in denen R1 Wasserstoff ist, sind: Examples of compounds of the formula (I) in which R 1 is hydrogen are:
Die Position der Substituenten bezieht sich auf den Sauerstoff. Die Position 3 ist para-ständig zur 2. Ringverknüpfung.The position of the substituents relates to the oxygen. The position is 3 para-constant to the 2nd ring link.
Weitere Beispiele sind: Other examples are:
Zu einer Mischung aus 500 ml Eisessig und 90 ml konz. Schwefelsäure werden
bei Raumtemperatur 24,4 ml einer wässrigen, 50 gew.-%igen Oxoessigsäure und
danach 91,7 g 4 -(1,1,3,3-Tetramethyl-butyl)-phenol zugegeben.
Nach Rühren über Nacht wird der entstandene Niederschlag abgesaugt, mit Eisessig
und danach mit Wasser gewaschen.
Nach Trocknung werden 81,1 g (90 % d. Th.) der Verbindung I-4 mit dem
Schmelzpunkt 125 bis 127°C erhalten.To a mixture of 500 ml glacial acetic acid and 90 ml conc. 24.4 ml of an aqueous 50% by weight oxoacetic acid and then 91.7 g of 4 - (1,1,3,3-tetramethylbutyl) phenol are added to sulfuric acid at room temperature.
After stirring overnight, the resulting precipitate is filtered off, washed with glacial acetic acid and then with water.
After drying, 81.1 g (90% of theory) of compound I-4 with a melting point of 125 to 127 ° C. are obtained.
In entsprechender Weise werden auch die übrigen genannten Verbindung erhalten. Bei herabgesetzter Reaktivität der phenolischen Komponente können verschärfte Reaktionsbedingungen erforderlich werden z.B. durch Erhöhung der Temperatur, Erhöhung der Konzentration an Schwefelsäure Durchführung in der Schmelze etc. Weiterhin kann die Schwefelsäure ganz oder teilweise durch andere Säuren ersetzt werden, z.B. durch p-Toluolsulfonsäure, Methansulfonsäure, Phosphorsäure, Polyphosphorsäure, Phthalsäure, Trifluoressigsäure, Borsäure u. dgl.The other compounds mentioned are obtained in a corresponding manner. If the reactivity of the phenolic component is reduced, it can be aggravated Reaction conditions become necessary e.g. by increasing the temperature, Increasing the concentration of sulfuric acid in the melt etc. Furthermore, all or part of the sulfuric acid can be replaced by other acids e.g. by p-toluenesulfonic acid, methanesulfonic acid, phosphoric acid, polyphosphoric acid, Phthalic acid, trifluoroacetic acid, boric acid and the like. like.
Verbindungen der Formel I, in denen R1 ein Acylrest bedeutet, können aus den entsprechenden Hydroxylverbindungen durch Umsetzung mit Säurechloriden oder Säureanhydriden hergestellt werden.Compounds of the formula I in which R 1 is an acyl radical can be prepared from the corresponding hydroxyl compounds by reaction with acid chlorides or acid anhydrides.
Die Verbindungen der Formel (I) werden bevorzugt in einer Menge von 5 bis 1000 mg/m2, insbesondere 10 bis 500 mg/m2 eingesetzt.The compounds of formula (I) are preferably used in an amount of 5 to 1000 mg / m 2 , in particular 10 to 500 mg / m 2 .
Die Verbindungen der Formel (I) können auch als Salz (Phenolat) vorliegen; als Kationen eignen sich Metallkationen und Ammoniumionen, insbesondere Alkalimetallionen und Trialkyl- oder Tetraalkylammoniumionen.The compounds of formula (I) can also be present as a salt (phenolate); as Cations are particularly suitable for metal cations and ammonium ions Alkali metal ions and trialkyl or tetraalkylammonium ions.
Beispiele für farbfotografische Materialien sind Farbnegativfilme, Farbumkehrfilme, Farbpositivfilme, farbfotografisches Papier, farbumkehrfotografisches Papier, farbempfindliche Materialien für das Farbdiffusionstransfer-Verfahren oder das Silberfarbbleich-Verfahren.Examples of color photographic materials are color negative films, color reversal films, Color positive films, color photographic paper, color reversal photographic paper, color-sensitive materials for the color diffusion transfer process or the silver color bleaching process.
Die fotografischen Materialien bestehen aus einem Träger, auf den wenigstens eine lichtempfindliche Silberhalogenidemulsionsschicht aufgebracht ist. Als Träger eignen sich insbesondere dünne Filme und Folien. Eine Übersicht über Trägermaterialien und auf deren Vorder- und Rückseite aufgetragene Hilfsschichten ist in Research Disclosure 37254, Teil 1 (1995), S. 285 dargestellt.The photographic materials consist of a support on which at least one photosensitive silver halide emulsion layer is applied. Suitable as a carrier especially thin films and foils. An overview of carrier materials and auxiliary layers applied to their front and back is in Research Disclosure 37254, Part 1 (1995), p. 285.
Die farbfotografischen Materialien enthalten üblicherweise mindestens je eine rotempfindliche, grünempfindliche und blauempfindliche Silberhalogenidemulsionsschicht sowie gegebenenfalls Zwischenschichten und Schutzschichten.The color photographic materials usually contain at least one red-sensitive, green sensitive and blue sensitive silver halide emulsion layer and optionally intermediate layers and protective layers.
Je nach Art des fotografischen Materials können diese Schichten unterschiedlich angeordnet sein. Dies sei für die wichtigsten Produkte dargestellt:Depending on the type of photographic material, these layers can vary be arranged. This is shown for the most important products:
Farbfotografische Filme wie Colornegativfilme und Colorumkehrfilme weisen in der nachfolgend angegebenen Reihenfolge auf dem Träger 2 oder 3 rotempfindliche, blaugrünkuppelnde Silberhalogenidemulsionsschichten, 2 oder 3 grünempfindliche, purpurkuppelnde Silberhalogenidemulsionsschichten und 2 oder 3 blauempfindliche, gelbkuppelnde Silberhalogenidemulsionsschichten auf. Die Schichten gleicher spektraler Empfindlichkeit unterscheiden sich in ihrer fotografischen Empfindlichkeit, wobei die weniger empfindlichen Teilschichten in der Regel näher zum Träger angeordnet sind als die höher empfindlichen Teilschichten.Color photographic films such as color negative films and color reversal films show in in the following order on the carrier 2 or 3 red-sensitive, cyan-coupling silver halide emulsion layers, 2 or 3 green-sensitive, purple-coupling silver halide emulsion layers and 2 or 3 blue-sensitive, yellow-coupling silver halide emulsion layers. The layers same spectral sensitivity differ in their photographic sensitivity, with the less sensitive sub-layers usually closer arranged to the carrier than the higher sensitive sub-layers.
Zwischen den grünempfindlichen und blauempfindlichen Schichten ist üblicherweise eine Gelbfilterschicht angebracht, die blaues Licht daran hindert, in die darunter liegenden Schichten zu gelangen.Between the green sensitive and blue sensitive layers is common a yellow filter layer is applied, which prevents blue light from entering the to get layers below.
Die Möglichkeiten der unterschiedlichen Schichtanordnungen und ihre Auswirkungen auf die fotografischen Eigenschaften werden in J. Inf. Rec. Mats., 1994, Vol. 22, Seiten 183 - 193 beschrieben.The possibilities of the different layer arrangements and their effects on the photographic properties are described in J. Inf. Rec. Mats., 1994, Vol. 22, pages 183-193.
Farbfotografisches Papier, das in der Regel wesentlich weniger lichtempfindlich ist als ein farbfotografischer Film, weist in der nachfolgend angegebenen Reihenfolge auf dem Träger üblicherweise je eine blauempfindliche, gelbkuppelnde Silberhalogenidemulsionsschicht, eine grünempfindliche, purpurkuppelnde Silberhalogenidemulsionsschicht und eine rotempfindliche, blaugrünkuppelnde Silberhalogenidemulsionsschicht auf; die Gelbfilterschicht kann entfallen. Color photographic paper, which is usually much less sensitive to light as a color photographic film, points in the order given below usually a blue-sensitive, yellow-coupling silver halide emulsion layer on the support, a green sensitive, purple coupling silver halide emulsion layer and a red sensitive, cyan-coupling silver halide emulsion layer on; the yellow filter layer can be omitted.
Abweichungen von Zahl und Anordnung der lichtempfindlichen Schichten können zur Erzielung bestimmter Ergebnisse vorgenommen werden. Zum Beispiel können alle hochempfindlichen Schichten zu einem Schichtpaket und alle niedrigempfindlichen Schichten zu einem anderen Schichtpaket in einem fotografischen Film zusammengefaßt sein, um die Empfindlichkeit zu steigern (DE-25 30 645).Deviations in the number and arrangement of the photosensitive layers can occur to achieve certain results. For example, you can all highly sensitive layers in one layer package and all low-sensitive layers Layers to another layer package in a photographic film be summarized to increase sensitivity (DE-25 30 645).
Wesentliche Bestandteile der fotografischen Emulsionsschichten sind Bindemittel, Silberhalogenidkörner und Farbkuppler.Essential components of the photographic emulsion layers are binders, Silver halide grains and color couplers.
Angaben über geeignete Bindemittel finden sich in Research Disclosure 37254, Teil 2 (1995), S. 286.Information on suitable binders can be found in Research Disclosure 37254, Part 2 (1995), p. 286.
Angaben über geeignete Silberhalogenidemulsionen, ihre Herstellung, Reifung, Stabilisierung und spektrale Sensibilisierung, einschließlich geeigneter Spektralsensibilisatoren finden sich in Research Disclosure 37254, Teil 3 (1995), S. 286 und in Research Disclosure 37038, Teil XV (1995), S. 89.Information about suitable silver halide emulsions, their preparation, maturation, Stabilization and spectral sensitization, including suitable spectral sensitizers can be found in Research Disclosure 37254, Part 3 (1995), pp. 286 and in Research Disclosure 37038, Part XV (1995), p. 89.
Fotografische Materialien mit Kameraempfindlichkeit enthalten üblicherweise Silberbromidiodid- oder Silberbromidiodidchloridemulsionen. Fotografische Kopiermaterialien enthalten entweder Silberchloridbromidemulsionen mit bis 80 mol-% AgBr oder Silberchloridbromidemulsionen mit über 95 mol-% AgCl.Photographic materials with camera sensitivity usually contain silver bromide iodide or silver bromide iodide chloride emulsions. Photographic copy materials contain either silver chloride bromide emulsions with up to 80 mol% AgBr or silver chloride bromide emulsions with over 95 mol% AgCl.
Angaben zu den Farbkupplern finden sich in Research Disclosure 37254, Teil 4 (1995), S. 288 und in Research Disclosure 37038, Teil II (1995), S. 80. Die maximale Absorption der aus den Kupplern und dem Farbentwickleroxidationsprodukt gebildeten Farbstoffe liegt vorzugsweise in den folgenden Bereichen: Gelbkuppler 430 bis 460 nm, Purpurkuppler 540 bis 560 nm, Blaugrünkuppler 630 bis 700 nm.Information on the color couplers can be found in Research Disclosure 37254, Part 4 (1995), p. 288 and in Research Disclosure 37038, Part II (1995), p. 80. The maximum absorption of that from the couplers and the color developer oxidation product Dyes formed are preferably in the following areas: Yellow coupler 430 to 460 nm, purple coupler 540 to 560 nm, cyan coupler 630 up to 700 nm.
In farbfotografischen Filmen werden zur Verbesserung von Empfindlichkeit, Körnigkeit, Schärfe und Farbtrennung häufig Verbindungen eingesetzt, die bei der Reaktion mit dem Entwickleroxidationsprodukt Verbindungen freisetzen, die fotografisch wirksam sind, z.B. DIR-Kuppler, die einen Entwicklungsinhibitor abspalten. In color photography films, to improve sensitivity, Graininess, sharpness and color separation are often used in compounds React with the developer oxidation product to release compounds that are photographic are effective, e.g. DIR couplers that release a development inhibitor.
Angaben zu solchen Verbindungen, insbesondere Kupplern, finden sich in Research Disclosure 37254, Teil 5 (1995), S. 290 und in Research Disclosure 37038, Teil XIV (1995), S. 86.Information on such connections, in particular couplers, can be found in Research Disclosure 37254, Part 5 (1995), p. 290 and in Research Disclosure 37038, Part XIV (1995), p. 86.
Die meist hydrophoben Farbkuppler, aber auch andere hydrophobe Bestandteile der Schichten, werden üblicherweise in hochsiedenden organischen Lösungsmitteln gelöst oder dispergiert. Diese Lösungen oder Dispersionen werden dann in einer wäßrigen Bindemittellösung (üblicherweise Gelatinelösung) emulgiert und liegen nach dem Trocknen der Schichten als feine Tröpfchen (0,05 bis 0,8 µm Durchmesser) in den Schichten vor.Mostly hydrophobic color couplers, but also other hydrophobic components of the layers, are usually in high-boiling organic solvents dissolved or dispersed. These solutions or dispersions are then in one emulsified aqueous binder solution (usually gelatin solution) and lie after drying the layers as fine droplets (0.05 to 0.8 µm diameter) in the layers before.
Geeignete hochsiedende organische Lösungsmittel, Methoden zur Einbringung in die Schichten eines fotografischen Materials und weitere Methoden, chemische Verbindungen in fotografische Schichten einzubringen, finden sich in Research Disclosure 37254, Teil 6 (1995), S. 292.Suitable high-boiling organic solvents, methods for incorporation into the layers of a photographic material and other methods, chemical Introducing connections into photographic layers can be found in Research Disclosure 37254, Part 6 (1995), p. 292.
Die in der Regel zwischen Schichten unterschiedlicher Spektralempfindlichkeit angeordneten nicht lichtempfindlichen Zwischenschichten können Mittel enthalten, die eine unerwünschte Diffusion von Entwickleroxidationsprodukten aus einer lichtempfindlichen in eine andere lichtempfindliche Schicht mit unterschiedlicher spektraler Sensibilisierung verhindern.The usually between layers of different spectral sensitivity arranged non-light-sensitive intermediate layers can contain agents which an undesirable diffusion of developer oxidation products from a photosensitive to another photosensitive layer with different prevent spectral sensitization.
Geeignete Verbindungen (Weißkuppler, Scavenger oder EOP-Fänger) finden sich in Research Disclosure 37254, Teil 7 (1995), S. 292 und in Research Disclosure 37038, Teil III (1995), S. 84.Suitable connections (white coupler, scavenger or EOP catcher) can be found in Research Disclosure 37254, Part 7 (1995), p. 292 and in Research Disclosure 37038, Part III (1995), p. 84.
Das fotografische Material kann weiterhin UV-Licht absorbierende Verbindungen, Weißtöner, Abstandshalter, Filterfarbstoffe, Formalinfänger, Lichtschutzmittel, Antioxidantien, DMin-Farbstoffe, Zusätze zur Verbesserung der Farbstoff-, Kuppler- und Weißenstabilität sowie zur Verringerung des Farbschleiers, Weichmacher (Latices), Biocide und anderes enthalten.The photographic material can also contain UV light-absorbing compounds, white toners, spacers, filter dyes, formalin scavengers, light stabilizers, antioxidants, D min dyes, additives to improve the stability of dyes, couplers and whites and to reduce the color fog, plasticizers (latices), Contain biocides and others.
Geeignete Verbindungen finden sich in Research Disclosure 37254, Teil 8 (1995), S. 292 und in Research Disclosure 37038, Teile IV, V, VI, VII, X, XI und XIII (1995), S. 84 ff. Suitable compounds can be found in Research Disclosure 37254, Part 8 (1995), P. 292 and in Research Disclosure 37038, parts IV, V, VI, VII, X, XI and XIII (1995), p. 84 ff.
Die Schichten farbfotografischer Materialien werden üblicherweise gehärtet, d.h., das verwendete Bindemittel, vorzugsweise Gelatine, wird durch geeignete chemische Verfahren vernetzt.The layers of color photographic materials are usually hardened, i.e. the binder used, preferably gelatin, is by suitable cross-linked chemical processes.
Geeignete Härtersubstanzen finden sich in Research Disclosure 37254, Teil 9 (1995), S. 294 und in Research Disclosure 37038, Teil XII (1995), Seite 86.Suitable hardener substances can be found in Research Disclosure 37254, Part 9 (1995), p. 294 and in Research Disclosure 37038, Part XII (1995), page 86.
Nach bildmäßiger Belichtung werden farbfotografische Materialien ihrem Charakter entsprechend nach unterschiedlichen Verfahren verarbeitet. Einzelheiten zu den Verfahrensweisen und dafür benötigte Chemikalien sind in Research Disclosure 37254, Teil 10 (1995), S. 294 sowie in Research Disclosure 37038, Teile XVI bis XXIII (1995), S. 95 ff. zusammen mit exemplarischen Materialien veröffentlicht.After photographic exposure, color photographic materials become their character processed according to different processes. Details of the Procedures and chemicals required for this are in Research Disclosure 37254, part 10 (1995), p. 294 and in Research Disclosure 37038, parts XVI to XXIII (1995), p. 95 ff. Published together with exemplary materials.
Die Verbindungen der Formel (I) werden insbesondere in wenigstens einer Nachbarschicht zu einer grünempfindlichen, wenigstens einen Purpurkuppler enthaltenden Silberhalogenidemulsionsschicht eingesetzt, deren Silberhalogenidemulsion eine Silberbromidchloridemulsion mit wenigstens 95 Mol-% AgCl ist.The compounds of formula (I) are in particular in at least one neighboring layer to a green sensitive, containing at least one purple coupler Silver halide emulsion layer used, the silver halide emulsion is a silver bromide chloride emulsion with at least 95 mol% AgCl.
Für diesen Fall kommen als Purpurkuppler insbesondere Pyrazolotriazolpurpurkuppler in Betracht. In this case, especially pyrazolotriazole purple couplers come as purple couplers into consideration.
Ein farbfotografisches Aufzeichnungsmaterial wurde hergestellt, indem auf einen Schichtträger aus beidseitig mit Polyethylen beschichtetem Papier die folgenden Schichten in der angegebenen Reihenfolge aufgetragen wurden. Die Mengenangaben beziehen sich jeweils auf 1 m2. Für den Silberhalogenidauftrag werden die entsprechenden Mengen AgNO3 angegeben.A color photographic recording material was produced by applying the following layers in the order given to a support made of paper coated on both sides with polyethylene. The quantities given relate to 1 m 2 . The corresponding amounts of AgNO 3 are given for the silver halide application.
- Schicht 1:Layer 1:
- (Substratschicht) 0,2 g Gelatine(Substrate layer) 0.2 g gelatin
- Schicht 2:Layer 2:
-
(blauempfindliche Schicht)
blauempfindliche Silberhalogenidemulsion (99,5 mol-% Chlorid,
0,5 mol-% Bromid, mittlerer Korndurchmesser 0,8 µm) aus
0,45 g AgNO3 mit
1,18 g Gelatine
0,55 g Gelbkuppler Y-1
0,1 g Weißkuppler W-1
0,2 g Farbstoffstabilisator ST-1
0,29 g Ölbildner OF-1
0,10 g Ölbildner OF-2(blue sensitive layer)
blue-sensitive silver halide emulsion (99.5 mol% chloride,
0.5 mol% bromide, average grain diameter 0.8 µm)
0.45 g AgNO 3 with
1.18 g gelatin
0.55 g yellow coupler Y-1
0.1 g white coupler W-1
0.2 g ST-1 dye stabilizer
0.29 g of oil former OF-1
0.10 g of oil former OF-2 - Schicht 3:Layer 3:
-
(Schutzschicht)
1,10 g Gelatine
0,07 g Verbindung SC-1
0,07 g Verbindung SC-2
0,07 g Trikresylphosphat (TKP)(Protective layer)
1.10 g gelatin
0.07 g of compound SC-1
0.07 g of compound SC-2
0.07 g tricresyl phosphate (CPM) - Schicht 4:Layer 4:
-
(grünempfindliche Schicht)
grünsibilisierte Silberhalogenidemulsion (99,5 mol-% Chlorid,
0,5 mol-% Bromid, mittlerer Korndurchmesser 0,6 µm) aus
0,58 g AgNO3 mit
1,08 g Gelatine
0,52 g Purpurkuppler M-1
0,24 g Farbstoffstabilisator ST-2
0,10 g Farbstoffstabilisator ST-3
0,25 g Dibutyladipat
0,25 g Isooctadecanol(green-sensitive layer) green-sensitized silver halide emulsion (99.5 mol% chloride,
0.5 mol% bromide, average grain diameter 0.6 µm)
0.58 g of AgNO 3 with
1.08 g gelatin
0.52 g purple coupler M-1
0.24 g ST-2 dye stabilizer
0.10 g ST-3 dye stabilizer
0.25 g dibutyl adipate
0.25 g isooctadecanol - Schicht 5:Layer 5:
-
(UV-Schutzschicht)
1,15 g Gelatine
0,2 g UV-Absorber UV-1
0,2 g UV-Absorber UV-2
0,2 g Ölbildner OF-3
0,07 g Verbindung SC-1
0,07 g Verbindung SC-2 0,04 g TKP(UV protective layer)
1.15 g gelatin
0.2 g UV absorber UV-1
0.2 g UV absorber UV-2
0.2 g of oil former OF-3
0.07 g of compound SC-1
0.07 g compound SC-2 0.04 g CPM - Schicht 6:Layer 6:
-
(rotempfindliche Schicht)
rotsensibilisierte Silberhalogenidemulsion (99,5 mol-% Chlorid,
0,5 mol-% Bromid, mittlerer Korndurchmesser 0,5 µm) aus
0,30 g AgNO3 mit
0,75 g Gelatine
0,2 g UV-Absorber UV-1
0,36 g Blaugrünkuppler C-1
0,12 g Farbstoffstabilisator ST-4
0,24 g TKP(red sensitive layer)
red-sensitized silver halide emulsion (99.5 mol% chloride,
0.5 mol% bromide, average grain diameter 0.5 µm)
0.30 g AgNO 3 with
0.75 g gelatin
0.2 g UV absorber UV-1
0.36 g of cyan coupler C-1
0.12 g ST-4 dye stabilizer
0.24 g CPM - Schicht 7:Layer 7:
-
(UV-Schutzschicht)
0,35 g Gelatine
0,15 g UV-Absorber UV-3
0,15 g Ölbildner OF-4(UV protective layer)
0.35 g gelatin
0.15 g UV absorber UV-3
0.15 g of oil generator OF-4 - Schicht 8:Layer 8:
-
(Schutzschicht)
0,9 g Gelatine
0,3 g Härtungsmittel H-1(Protective layer)
0.9 g gelatin
0.3 g of H-1 curing agent
Im Schichtaufbau des Beispiels 1 wurden folgende Verbindungen verwendet: OF - 1 Adipinsäurepolyester mit 1,3-Butandiol und 1,4-Butandiol The following compounds were used in the layer structure of Example 1: OF - 1 adipic acid polyester with 1,3-butanediol and 1,4-butanediol
Die Proben 2 bis 14 werden hergestellt wie Probe 1 mit dem Unterschied, daß in
den Schichten 2, 3, 4 und 5 die Verbindungen Y-1 , SC-1, SC-2 und M-1 durch
die in Tabelle 1 angegebenen ausgetauscht werden. Außerdem wurde der
Silberauftrag in der Schicht 4 bei den Proben 4 bis 9 auf 0,28 g und bei den
Proben 10 bis 14 auf 0,22 g gesenkt.
Je eine Probe wurde hinter einem Graukeil mit blauem, grünem bzw. rotem Licht belichtet und wie folgt verarbeitet:One sample each was behind a gray wedge with blue, green and red light exposed and processed as follows:
Anschließend wurde bei der mit grünem Licht belichteten Probe die prozentuale
bg-Dichte (Dbg) bei der pp-Dichte (Dpp) 1,0 bestimmt (Tabelle 2). Danach wurden
alle Proben dem Licht einer für Tageslicht normierten Xenonlampe ausgesetzt und
mit 15·106 Lux·h bestrahlt. Die prozentuale Dichteabnahme ΔDgb, ΔDpp bzw.
ΔDbg nach der Bestrahlung wurde bei der Anfangsdichte D = 1,0 bestimmt
(Tabelle 2).
Wie Tabelle 2 zeigt, verhindern die erfindungsgemäßen Verbindungen effektiv die Mitkupplung ohne die Farbstoffstabilität nachteilig zu beeinflussen.As Table 2 shows, the compounds of the invention effectively prevent that Coupling without adversely affecting the dye stability.
In den Proben 2 bis 14 erstmals verwendete Verbindungen: Compounds used for the first time in samples 2 to 14:
Ein farbfotographisches Aufzeichnungsmaterial für die Colornegativentwicklung
wurde hergestellt (Probe 15 - Vergleich), indem auf einen mit einer Haftschicht
versehenen transparenten Schichtträger aus Cellulosetriacetat mit einer Dicke von
120 µm die folgenden Schichten in der angegebenen Reihenfolge aufgetragen
wurden. Die Mengen sind in g/m2 angegeben. Für den Silberhalogenidauftrag
werden die entsprechenden Mengen AgNO3 angegeben. Alle Silberhalogenidemulsionen
waren pro 100 g AgNO3 mit 0,1 g 4-Hydroxy-6-methyl-1,3,3a,7-tetraazainden
stabilisiert. Die Silberhalogenidemulsionen sind durch die Halogenidzusammensetzung
und hinsichtlich der Korngröße durch den Volumenschwerpunkt
(VSP) charakterisiert. Der Volumenschwerpunkt hat die Dimension einer Länge
[µm] und wird bestimmt über die Beziehung:
(2,4 mol-% Iodid; 10,5 mol-% Chlorid; VSP 0,35)red-sensitized silver bromide iodide chloride emulsion
(2.4 mol% iodide; 10.5 mol% chloride; VSP 0.35)
(10,0 mol-% Iodid; VSP 0,56)red-sensitized silver bromoiodide emulsion
(10.0 mol% iodide; VSP 0.56)
(6,8 mol-% Iodid; VSP 1,2)red-sensitized silver bromoiodide emulsion
(6.8 mol% iodide; VSP 1.2)
(9,5 mol-% Iodid; 10,4 mol-% Chlorid; VSP 0,5)green-sensitized silver bromide iodide chloride emulsion
(9.5 mol% iodide; 10.4 mol% chloride; VSP 0.5)
(10,0 mol-% Iodid; VSP 0,56)green-sensitized silver bromide iodide chloride emulsion
(10.0 mol% iodide; VSP 0.56)
(6,8 mol-% Iodid; VSP 1,1)green-sensitized silver bromoiodide emulsion
(6.8 mol% iodide; VSP 1.1)
(6,0 mol-% Iodid; VSP 0,78)blue-sensitized silver bromoiodide emulsion
(6.0 mol% iodide; VSP 0.78)
(8,8 mol-% Iodid; 15,0 mol-% Chlorid; VSP 0,77)blue-sensitized silver bromide iodide chloride emulsion
(8.8 mol% iodide; 15.0 mol% chloride; VSP 0.77)
(12,0 mol-% lodid; VSP 1,2)blue-sensitized silver bromoiodide emulsion
(12.0 mol% iodide; VSP 1.2)
(4,0 mol-% Iodid; VSP 0,05)Mikrat - silver bromide iodide emulsion
(4.0 mol% iodide; VSP 0.05)
In Beispiel 2 verwendete Verbindungen: Compounds used in Example 2:
Die farblosen und farbigen Kuppler wurden jeweils zusammen mit der gleichen Menge an Trikresylphosphat (TKP) nach den in der Technik bekannten Emulgiermethoden eingebracht.The colorless and colored couplers were used together with the same Amount of tricresyl phosphate (CPM) according to the emulsification methods known in the art brought in.
Die Proben 16 bis 18 unterscheiden sich von Probe 15 dadurch, daß sie in der
Schicht 1 zusätzlich Verbindungen der Formel (I) (g/m2) enthalten. Die Proben
wurden anschließend hinter einem graduiertem Graukeil mit Tageslicht belichtet.
Danach wurden die Materialien nach dem bei E. Ch. Gehret, The British J. of
Photography 1974, S. 597 beschriebenen Prozeß verarbeitet. Aus den erhaltenen
Proben wurden die relative Rotempfindlichkeit und der Blaugrünschleier gemessen.
Die Ergebnisse sind in Tabelle 3 wiedergegeben.
Die Proben 19 bis 24 unterscheiden sich von Probe 15 dadurch, daß in der Schicht 5 zusätzlich 0,125 mmol der in Tabelle 4 aufgeführten Verbindungen/m2 eingesetzt wurden. Die Proben 23 und 24 enthielten stattdessen Weißkuppler W-1 bzw. W-2 in einer Menge von 0,125 mmol/m2.Samples 19 to 24 differ from sample 15 in that an additional 0.125 mmol of the compounds listed in table 4 / m 2 were used in layer 5. Samples 23 and 24 instead contained white couplers W-1 and W-2 in an amount of 0.125 mmol / m 2 .
Die Proben wurden wie die Proben 15 bis 18 verarbeitet. Es wurden die
Purpurdichte D1 im Punkt E + logH nach dreitägiger Lagerung bei 20°C und D2
nach dreitägiger Lagerung bei 60°C/90 % relativer Feuchte gemessen und die Differenz
D2-D1 sowie der Purpurschleier (Dmin) nach Lagerung bei Raumtemperaturen
bestimmt (E wurde im Punkt 0,2 über Schleier bestimmt). Die Ergebnisse
sind in Tabelle 4 dargestellt:
Weißkuppler W 2 hat die Formel: White coupler W 2 has the formula:
Aus den Ergebnissen der Tabelle 4 läßt sich ersehen, daß die erfindungsgemäßen Verbindungen den Purpurschleier vermindern, ohne daß sich die Differenz D2-D1 erhöht. Die Differenz D2-D1 ist ein Maß für die Stabilität des entwickelten Bildes, da damit Aussagen über sich ändernde Printbedingungen beim Lagern des entwickelten CN-Bildes möglich sind.It can be seen from the results in Table 4 that the compounds according to the invention reduce the purple haze without the difference D 2 -D 1 increasing. The difference D 2 -D 1 is a measure of the stability of the developed image, since it allows statements about changing print conditions when storing the developed CN image.
Claims (7)
- Colour photographic silver halide material having a support and at least one silver halide emulsion layer, characterised in that at least one layer contains at least one compound of the general formula (I) in which
- R1
- means hydrogen, alkyl or acyl,
- R2, R3
- mutually independently mean alkyl, cycloalkyl, alkenyl, aryl, halogen, OR4, SR5, NR6R7, nitro, cyano, SO2R8, COOR9, COR10 or hetaryl,
- R4, R5, R9
- mutually independently mean alkyl, cycloalkyl, alkenyl, aryl or hetaryl,
- R6, R7
- mutually independently mean H, R4, COR10, COOR9, SO2R8,
- R8, R10
- mutually independently mean alkyl, cycloalkyl, alkenyl, aryl, hetaryl or NR6R7,
- n, m
- mean 0, 1, 2, 3 or 4 or two residues R2 or R3 may each mean a fused carbo- or heterocyclic ring or the compounds of formula I are linked to a polymer chain via R1, R2 or R3.
- Colour photographic silver halide material according to claim 1, characterised in that R1 means hydrogen or acyl, R2 is identical to R3 and m is identical to n.
- Colour photographic silver halide material according to claim 1, characterised in that R1 means hydrogen and R2 and R3 mean alkyl, wherein the sum of C atoms in the alkyl residues R2 and R3 is ≥ 8.
- Colour photographic silver halide material according to claim 1, characterised in that the compounds of the formula (I) are used in a quantity of 5 to 1000 mg/m2 of material.
- Colour photographic silver halide material according to claim 1, characterised in that it contains silver chloride-bromide emulsions containing above 95 mol.% of AgCl.
- Colour photographic silver halide material according to claim 5, characterised in that the material contains at least one green-sensitive silver halide emulsion layer containing a magenta coupler and the compounds of the formula (I) are used in at least one layer adjacent to the green-sensitive silver halide emulsion layer.
- Colour photographic silver halide material according to claim 6, characterised in that the magenta coupler is a pyrazolotriazole magenta coupler.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19714614 | 1997-04-09 | ||
DE19714614A DE19714614A1 (en) | 1997-04-09 | 1997-04-09 | Color photographic silver halide material |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0871066A1 EP0871066A1 (en) | 1998-10-14 |
EP0871066B1 true EP0871066B1 (en) | 2002-06-19 |
Family
ID=7825887
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP98105593A Expired - Lifetime EP0871066B1 (en) | 1997-04-09 | 1998-03-27 | Colour photographic silver halide material |
Country Status (4)
Country | Link |
---|---|
US (1) | US5981160A (en) |
EP (1) | EP0871066B1 (en) |
JP (1) | JP3190617B2 (en) |
DE (2) | DE19714614A1 (en) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2343007B (en) * | 1998-10-19 | 2001-11-07 | Ciba Sc Holding Ag | Colour photographic material |
DE19916650A1 (en) | 1999-04-14 | 2000-10-19 | Agfa Gevaert Ag | Negative color photographic material, useful as copying material, contains 3-(2-hydroxyphenyl)-benzofuran-2-one compound as scavenger in light-insensitive layer further from base than any light-sensitive layer |
DE19938508A1 (en) | 1999-08-13 | 2001-02-15 | Agfa Gevaert Ag | A gelatin containing silver halide material, useful in color film and copying, comprises a light sensitive silver halide emulsion layer containing a 3-benzyl substituted-2-coumaranone compound. |
EP1109062A1 (en) | 1999-12-17 | 2001-06-20 | Agfa-Gevaert N.V. | Colour photographic silver halide material |
TW593303B (en) * | 2001-09-11 | 2004-06-21 | Ciba Sc Holding Ag | Stabilization of synthetic polymers |
CN102076321A (en) * | 2008-06-27 | 2011-05-25 | 巴斯夫欧洲公司 | Stabilization of body-care and household products |
TWI403507B (en) * | 2011-03-17 | 2013-08-01 | Chitec Technology Co Ltd | Benzofuranone derivatives and application of the same |
RU2732401C2 (en) | 2016-01-21 | 2020-09-16 | Басф Се | Additive mixture for polyol and polyurethane stabilization |
WO2023030859A1 (en) | 2021-09-02 | 2023-03-09 | Basf Se | Stabilizer combination for preventing degradation of synthetic polymers |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3006268A1 (en) * | 1980-02-20 | 1981-08-27 | Agfa-Gevaert Ag, 5090 Leverkusen | COLOR PHOTOGRAPHIC RECORDING MATERIAL WITH NON-DIFFUSING ELECTRON DONOR PRECURSOR CONNECTIONS |
US4369243A (en) * | 1981-03-06 | 1983-01-18 | Agfa-Gevaert Aktiengesellschaft | Photographic recording material for diffusion processes and useful non-diffusing sulfilimine compounds |
DE3215834A1 (en) * | 1982-04-28 | 1983-11-03 | Agfa-Gevaert Ag, 5090 Leverkusen | PHOTOGRAPHIC RECORDING MATERIAL FOR DIFFUSION PROCESSES AND SUITABLE NEW NON-DIFFUSING SULFILIMINE COMPOUNDS |
TW260686B (en) * | 1992-05-22 | 1995-10-21 | Ciba Geigy | |
DE19749083A1 (en) * | 1997-11-06 | 1998-07-23 | Agfa Gevaert Ag | Colour photographic material useful for photographic film or paper |
-
1997
- 1997-04-09 DE DE19714614A patent/DE19714614A1/en not_active Withdrawn
-
1998
- 1998-03-27 DE DE59804481T patent/DE59804481D1/en not_active Expired - Fee Related
- 1998-03-27 EP EP98105593A patent/EP0871066B1/en not_active Expired - Lifetime
- 1998-04-02 US US09/053,920 patent/US5981160A/en not_active Expired - Fee Related
- 1998-04-07 JP JP11012398A patent/JP3190617B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
DE59804481D1 (en) | 2002-07-25 |
DE19714614A1 (en) | 1998-10-15 |
JPH10282615A (en) | 1998-10-23 |
US5981160A (en) | 1999-11-09 |
EP0871066A1 (en) | 1998-10-14 |
JP3190617B2 (en) | 2001-07-23 |
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