US3725063A - Developer scavengers for image transfer systems - Google Patents
Developer scavengers for image transfer systems Download PDFInfo
- Publication number
- US3725063A US3725063A US00106281A US3725063DA US3725063A US 3725063 A US3725063 A US 3725063A US 00106281 A US00106281 A US 00106281A US 3725063D A US3725063D A US 3725063DA US 3725063 A US3725063 A US 3725063A
- Authority
- US
- United States
- Prior art keywords
- layer
- radical
- dye
- silver halide
- developing agent
- 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
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- 238000012546 transfer Methods 0.000 title claims abstract description 22
- 239000000975 dye Substances 0.000 claims abstract description 141
- 239000002516 radical scavenger Substances 0.000 claims abstract description 45
- LWGNRDQWNYOBAM-UHFFFAOYSA-N hydrogen sulfite;oxomethylideneazanium Chemical compound N=C=O.OS(O)=O LWGNRDQWNYOBAM-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000011230 binding agent Substances 0.000 claims abstract description 17
- 239000010410 layer Substances 0.000 claims description 224
- -1 silver halide Chemical class 0.000 claims description 139
- 239000000839 emulsion Substances 0.000 claims description 102
- 229910052709 silver Inorganic materials 0.000 claims description 82
- 239000004332 silver Substances 0.000 claims description 82
- 239000003795 chemical substances by application Substances 0.000 claims description 80
- 238000012545 processing Methods 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 41
- 239000000463 material Substances 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 29
- 238000011161 development Methods 0.000 claims description 22
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- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 15
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- 230000000694 effects Effects 0.000 claims description 14
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- QPWRBETWOKXASJ-UHFFFAOYSA-N [2-amino-5-(diethylamino)phenyl]methanol Chemical compound CCN(CC)C1=CC=C(N)C(CO)=C1 QPWRBETWOKXASJ-UHFFFAOYSA-N 0.000 description 1
- MPLZNPZPPXERDA-UHFFFAOYSA-N [4-(diethylamino)-2-methylphenyl]azanium;chloride Chemical compound [Cl-].CC[NH+](CC)C1=CC=C(N)C(C)=C1 MPLZNPZPPXERDA-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- AEMQUICCWRPKDB-UHFFFAOYSA-N acetic acid;cyclohexane-1,2-dicarboxylic acid Chemical compound CC(O)=O.OC(=O)C1CCCCC1C(O)=O AEMQUICCWRPKDB-UHFFFAOYSA-N 0.000 description 1
- NMUTVZGCFBKTRR-UHFFFAOYSA-N acetyl acetate;zirconium Chemical compound [Zr].CC(=O)OC(C)=O NMUTVZGCFBKTRR-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 229920006322 acrylamide copolymer Polymers 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000007754 air knife coating Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical class NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- AGXUVMPSUKZYDT-UHFFFAOYSA-L barium(2+);octadecanoate Chemical compound [Ba+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AGXUVMPSUKZYDT-UHFFFAOYSA-L 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001661 cadmium Chemical class 0.000 description 1
- 239000000648 calcium alginate Substances 0.000 description 1
- 235000010410 calcium alginate Nutrition 0.000 description 1
- 229960002681 calcium alginate Drugs 0.000 description 1
- OKHHGHGGPDJQHR-YMOPUZKJSA-L calcium;(2s,3s,4s,5s,6r)-6-[(2r,3s,4r,5s,6r)-2-carboxy-6-[(2r,3s,4r,5s,6r)-2-carboxylato-4,5,6-trihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate Chemical compound [Ca+2].O[C@@H]1[C@H](O)[C@H](O)O[C@@H](C([O-])=O)[C@H]1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@H](O2)C([O-])=O)O)[C@H](C(O)=O)O1 OKHHGHGGPDJQHR-YMOPUZKJSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000001240 enamine group Chemical group 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000007765 extrusion coating Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002343 gold Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- NNKYSIRIWMMQFW-UHFFFAOYSA-N hydrogen sulfate;2-hydroxyethyl(phenyl)azanium Chemical compound OS([O-])(=O)=O.OCC[NH2+]C1=CC=CC=C1 NNKYSIRIWMMQFW-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- RSAZYXZUJROYKR-UHFFFAOYSA-N indophenol Chemical compound C1=CC(O)=CC=C1N=C1C=CC(=O)C=C1 RSAZYXZUJROYKR-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical compound C=CN=C=O WARQUFORVQESFF-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 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
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000013047 polymeric layer Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003236 pyrrolines Chemical class 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- ZFMRLFXUPVQYAU-UHFFFAOYSA-N sodium 5-[[4-[4-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-2-hydroxybenzoic acid Chemical compound C1=CC(=CC=C1C2=CC=C(C=C2)N=NC3=C(C=C4C=CC(=CC4=C3O)N)S(=O)(=O)O)N=NC5=CC(=C(C=C5)O)C(=O)O.[Na+] ZFMRLFXUPVQYAU-UHFFFAOYSA-N 0.000 description 1
- QJQRNDGUWQVAEV-AAFSJPGBSA-M sodium bisulfite adduct Chemical compound [Na+].[O-]S(=O)(=O)C([C@H]1N(C(C2=C3)=O)C=C(C1)/C=C/C(=O)N(C)C)NC2=CC1=C3OCO1 QJQRNDGUWQVAEV-AAFSJPGBSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- JRQGFDPXVPTSJU-UHFFFAOYSA-L sodium zirconium(4+) sulfate Chemical compound [Na+].[Zr+4].[O-]S([O-])(=O)=O JRQGFDPXVPTSJU-UHFFFAOYSA-L 0.000 description 1
- RHNKWXNQMATDHE-UHFFFAOYSA-M sodium;2-(2-methylprop-2-enoyloxy)ethyl sulfate Chemical compound [Na+].CC(=C)C(=O)OCCOS([O-])(=O)=O RHNKWXNQMATDHE-UHFFFAOYSA-M 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003498 tellurium compounds Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 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
- G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
- G03C8/02—Photosensitive materials characterised by the image-forming section
- G03C8/08—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic 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
- G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
Definitions
- a developer scavenger layer comprising an isocyanate-bisulflte addition product and a polymeric S "96/29 binder is useful for reducing background stain in a dye [58] image receiving element of a color diffusion transfer Field of Search .Q ..96/29, 56
- the above film unit containing an aromatic primary amino color developing agent, preferably in the rupturable container, and an isocyanate-bisulfite addition product in a polymeric binder which is capable of reacting with unused aromatic primary amino color developing agent to form a colorless urea reaction product.
- the developer-scavenging, isocyanate-bisulfite addition products or adducts employed in our invention have the following general formula:
- R represents an acyclic alkyl group, including a substituted acyclic alkyl group, preferably a lower acyclic alkyl group, i.e., having one to six carbon atoms in the chain such as methyl, ethyl, isopropyl, benzyl, hexyl, carbethoxymethyl, etc.; an alkenyl group such as vinyl, isopropenyl, allyl, etc., preferably having one to six carbon atoms; an alicyclic group typically having four to six carbon atoms in the ring such as cyclohexyl, cyclopentyl, cyclobutyl, etc.; or an aryl group, including a substituted aryl group, such as phenyl, tolyl, naphthyl, methoxyphenyl, biphenylyl, etc.;
- R represents a hydrogen atom or an alkyl group, including a substituted alkyl group as described above for R; and a M represents an alkali metal ion, e.g., a sodium, potassium or ammonium ion.
- the bisulfite adduct functions as a developer scavenger precursor and under the basic conditions of color development reverts to the parent isocyanate compound which in turn reacts with excess unused aromatic primary amino color developing agent to form a colorless product, thereby reducing the yellowish-brown stain which results from the diffusion of unused aromatic primary amino color developing agent into the image-receiving element. Therefore, any isocyanate bisulfite addition product which is compatible with the photosensitive and image-receiving elements can be employed in the practice of the invention provided the addition product reverts under alkaline conditions to the parent isocyanate compound which in turn will react with primary amino color developing agent to form a colorless product.
- the novel dye image-receiving element comprises a support having thereon the following layers:
- the image dyes formed in the respective blue, green and red-sensitive silver halide emulsion layers diffuse out of the photosensitive element through the viscous developer composition and into the dye image-receiving layer, e.g., into the dye image-receiving element described above, where the dyes are mordanted to form the transferred image.
- the timing layer if one is present, prevents the diffusion of color developer into the scavenger layer for the time necessary to ensure the efficient use of the aromatic primary amino color developing agent in the photosensitive element.
- auxiliary developer scavenger layer comprising the isocyanate-bisulfite adducts described herein can be located on the opaque process sheet.
- each silver halide emulsion layer in the photosensitive element there is associated with each silver halide emulsion layer in the photosensitive element a dye image-providing material comprising a nondiffusible coupler which produces a diffusible dye on reaction with oxidized aromatic primary amino color developing agent in alkaline processing composition.
- the nondiffusible couplers employed in this invention include those having formulas:
- BALL LINK f (COUP SOL) wherein l. DYE is a dye radical exhibiting selective absorption in the visible spectrum and containing an acidic solubilizing radical;
- BALL is a photographically inert organic ballasting radical of such molecular size and configuration as to render such coupler nondiffusible during development in the alkaline processing composition
- SOL is a hydrogen atom or an acidic solubilizing group when the color developing agent contains an acidic solubilizing group, and SOL is an acidic solubilizing group when the color developing agent is free of an acidic solubilizing group;
- n is an integer of l to 2 when LINK is an alkylidene radical, and n is I when LINK is an azo radical, a mercuri radical, an oxy radical, a thio radical, a dithio radical or an azoxy radical.
- the acidic solubilizing radicals attached to the diffusible dye producing couplers described above can be solubilizing radicals which when attached to the coupler or developer moieties of the dyes, render the dyes diffusible in alkaline processing compositions.
- Typical of such radicals are carboxylic, sulfonic, ionizable sulfonamide, and hydroxy-substituted groups that lend to dyes negative charges.
- ballast groups in the diffusible dyeproducing coupler compounds described above are not critical as long as they confer nondiffusibility to the coupler compounds.
- Typical ballast groups include long chain alkyl radicals linked directly or indirectly to the coupler molecules as well as aromatic radicals of the benzene and naphthalene series, etc., linked directly or indirectly to the coupler molecules by a splittable linkage, or by a removable or irremovable but otherwise nonfunctional linkage depending upon the nature of the coupler compound.
- Useful ballast groups have at least eight carbon atoms.
- Typical dye radical substituents include azo, azomethine, indoaniline, indophenol, anthraquinone and related dye radicals well known in the art that exhibit selective absorption in the visible spectrum.
- the dye radicals contain acidic solubilizing moieties.
- the cyanproducing coupler has the formula BALL--O CYANCOUP
- the yellowproducing coupler has the formula BALLOYELL- COUP wherein:
- nondiffusing used herein as applied to the couplers, has the meaning commonly applied to the term in color photography and denotes materials which for all practical purposes do not migrate or wander through organic colloid layers, such as gelatin, comprising the sensitive elements of the invention. The same meaning is to be attached to the term immobile.
- diffusible as applied to the dyes formed from the nondiffusing couplers in this invention has the converse meaning and denotes materials having the property of diffusing effectively through the colloid layers of the sensitive elements in the presence of the nondiffusing materials from which they are derived.
- Mobile has the same meaning.
- the color of the diffusible dye is determined by the color of the preformed dye moiety (DYE), the color of the reaction product of color developer oxidation product and the coupler moiety (COUP) being unimportant to the color of the diffusible image.
- the connecting radical (LINK) is split and a diffusible dye is formed with the color developing agent oxidation product and the coupling portion (COUP) of the coupler which diffuses imagewise to a reception layer. Diffusibility is imparted to the dye by an acidic solubilizing group attached to a noncoupling position of the coupling portion (COUP) of the coupler or to the color developing agent. The ballasting portion of the coupler remains immobile.
- the color of the diffusible dye is determined by the color of the reaction product of color developer oxidation product and the coupler moiety (COUP).
- Suitable fogging agents include the hydrazines disclosed in Ives U.S. Pat. No. 2,588,982 issued Mar. 11, 1952 and 2,563,785 issued Aug. 7, 1951; the hydrazides and hydrazones disclosed in Whitmore U.S. Pat. No. 3,227,552 issued Jan. 4, l966;hydrazone quaternary salts described in Lincoln and Heseltine application Ser. No. 828,064 filed Apr.
- the merocyanine dyes can contain the basic nuclei mentioned above as well as acid nuclei such as thiohydantoins, rhodanines, oxazolidenediones, thiazolidenediones, barbituric acids,. thiazolineones, and malononitrile.
- acid nuclei can be substituted with alkyl, alkylene, phenyl, carboxyalkyl, sulfoalkyl, hydroxyalkyl, alkoxyalkyl, alkylamino groups, or heterocyclic nuclei. Combinations of these dyes can be used, if desired.
- supersensitizing addenda which do not absorb visible light
- addenda which do not absorb visible light
- ascorbic acid derivatives for instance, ascorbic acid derivatives, azaindenes, cadmium salts, and organic sulfonic acids as described in Mc- Fall et al. U.S. Pat. No. 2,933,390 and Jones et al. U.S. Pat. No. 2,937,089.
- the silver halide emulsions used in this invention may contain speed increasing compounds vsuch as polyalkylene glycols, cationic surface active agents and thioethers or combinations of these as described in Piper U.S. Pat. No. 2,886,437; Dann et al. U.S. Pat. No. 3,046,134; Carroll et al. U.S. Pat. No. 2,944,900; and Goffe U.S. Pat. NO. 3,294,540.
- speed increasing compounds v such as polyalkylene glycols, cationic surface active agents and thioethers or combinations of these as described in Piper U.S. Pat. No. 2,886,437; Dann et al. U.S. Pat. No. 3,046,134; Carroll et al. U.S. Pat. No. 2,944,900; and Goffe U.S. Pat. NO. 3,294,540.
- interlayers are generally employed between the various photosensitive color-forming units to scavenge oxidized developing agent and prevent it from forming an unwanted dye in another color-forming unit.
- Such interlayers would generally comprise a hydrophilic polymer such as gelatin and an immobilizing coupler, which is capable of reacting with oxidized aromatic primary amino color developing agent to form an immobile product.
- the aromatic primary amino color developing agent employed in the abovedescribed embodiments is preferably present in the alkaline processing composition in the rupturable pod.
- the color developing agent can also be incorporated into the negative portion of the film unit as a separate layer, e.g., by employing a Schiff base derivative of an aromatic primary amino color developing agent such as that formed by reacting o-sulfobenzaldehyde and N,N- diethyl-3-methyl-4-aminoaniline.
- a Schiff base derivative of an aromatic primary amino color developing agent such as that formed by reacting o-sulfobenzaldehyde and N,N- diethyl-3-methyl-4-aminoaniline.
- Such incorporated developing agent will be activated by the alkaline processing composition.
- the incorporated developing agent can be positioned in any layer of the photosensitive element from which it can be readily made available for development upon activation with alkaline processing composition, it is generally either incorporated in the light-sensitive silver halide emulsion layers or in layers contiguous thereto.
- each silver halide emulsion layer containing a dye imageproviding material or having the dye image-providingmaterial present in a contiguous layer may be separated from the other silver halide emulsion layers in the negative portion of the film unit by materials in addition to those described above, including gelatin, calcium alginate, or any of those disclosed in U.S. Pat. No.
- the silver halide emulsion layers in the invention com approximate only and can be modified according to the product desired.
- suitable hydrophilic materials include both naturally-occurring substances such as proteins, cellulose derivatives, polysaccharides such as dextran, gum arabic and the like; and synthetic polymeric substances such as water soluble polyvinyl compounds like poly(viny1pyrrolidone), acrylamide polymers and the like.
- the photographic emulsion layers andother layers of a photographic element employed in the practice of this invention can also contain alone or in combination with hydrophilic, water-permeable colloids, other synthetic polymeric compounds such as dispersed vinyl compounds such as in latex form and particularly those which increase the dimensional stability of the photo graphic materials.
- Suitable synthetic polymers include those described, for example, in Nottorf U.S. Pat. No. 3,142,568, issued July 28, 1964; White U.S. Pat. No. 3,193,386, issued July 6, 1965; Houck et a1.
- the alkaline processing composition employed in this invention is the conventional aqueous solution of an alkaline material, e.g., sodium hydroxide, sodium carbonate or an amine such as diethylamine, preferably possessing a pH in excess of 12.
- the solution also preferably contains a viscosity-increasing compound such as a high molecular weight polymer, e.g., a watersoluble ether inert to alkaline solutions such as hydroxyethyl cellulose or alkali metal salts of carboxymethyl cellulose such as sodium carboxymethyl cellulose.
- a concentration of viscosity-increasing compound of about 1 to about 5 percent by weight of the processing composition is preferred which will impart thereto a viscosity of about 100 cps. to about 200,000 cps.
- an opacifying agent e.g., TiO carbon black, etc. may be added to the processing composition.
- the alkaline solution-permeable, substantially opaque, light-reflective layer employed in certain embodiments of integral photographic film units of our invention can generally comprise any opacifier dispersed in a binder as long as it has the desired properties. Particularly desirable are white light-reflective layers since they would be esthetically pleasing backgrounds on which to view a transferred dye image and would also possess the optical properties desired for reflection of incident radiation.
- Suitable opacifying agents include titanium dioxide, barium sulfate, zinc oxide, barium stearate, silver flake, silicates, alumina, zirconium oxide, zirconium acetyl acetate, sodium zirconium sulfate, kaolin, mica, or mixtures thereof in widely varying amounts depending upon the degree of opacity desired.
- the opacifying agents may be dispersed in any binder such as an alkaline solution-permeable polymeric matrix such as, for example, gelatin, polyvinyl alcohol, and the like.
- Brightening agents such as the stilbenes, coumarins, triazines and oxazoles can also be added to the light-reflective layer, if desired.
- dark-colored opacifying agents may be added to it, e.g., carbon black, nigrosine dyes, etc.
- the supports for the photographic elements of this invention can be any material as long as it does not deleteriously effect the photographic properties of the film unit and is dimensionally stable.
- Typical flexible sheet materials include cellulose nitrate film, cellulose acetate film, poly(vinyl acetal) film, polystyrene film, poly(ethyleneterephthalate) film, polycarbonate film, poly-a-olefins such as polyethylene and polypropylene film, and related films or resinous materials as well as glass.
- the support is usually about 2 to 6 mils. in thickness.
- dotwise coating such as would be obtained using a gravure printing technique, could also be employed.
- small dots of blue, green and red-sensitive emulsions have associated therewith, respectively, dots of yellow, magenta and cyan color-providing substances. After development, the transferred dyes would tend to fuse together into a continuous tone.
- the photographic layers employed in the practice of this invention can contain surfactants such as saponin, anionic compounds such as the alkyl aryl sulfonates described in Baldsiefen U.S. Pat. No. 2,600,831; amphoteric compounds such as those described in Ben- Ezra U.S. Pat. No. 3,133,816; and water soluble adducts of glycidol and an alkyl phenol such as those described in Olin Mathieson British Pat. No. 1,022,878.
- surfactants such as saponin, anionic compounds such as the alkyl aryl sulfonates described in Baldsiefen U.S. Pat. No. 2,600,831; amphoteric compounds such as those described in Ben- Ezra U.S. Pat. No. 3,133,816; and water soluble adducts of glycidol and an alkyl phenol such as those described in Olin Mathieson British Pat. No. 1,02
- the photographic layers used in the practice of this invention can be coated by various coating procedures including dip coating, air knife coating, curtain coating, or extrusion coating using hoppers of the type described in Beguin U.S. Pat. No. 2,681,294. If desired, two or more layers can be coated simultaneously by the procedures described in Russell US. Pat. No. 2,761,791 and Wynn British Pat. No. 837,095. This invention also can be used for silver halide layers coated by vacuum evaporation as described in British Pat No. 968,453 and Lu Valle etal. US. Pat. No. 3,219,451.
- the photographic and other hardenable layers used in the practice of this invention can be hardened by various organic or inorganic hardeners, alone or in combination, such as the aldehydes, and blocked aldehydes, ketones, carbocyclic and carbonic acid derivatives, sulfonate esters, sulfonyl halides and vinyl sulfonyl ethers, active halogen compounds, epoxy compounds, aziridines, active' olefin, isocyanates, carbodiimides, mixed function hardeners and polymeric hardeners such as oxidized polysaccharides like dialdehyde starch and oxyguargum and the like.
- various organic or inorganic hardeners such as the aldehydes, and blocked aldehydes, ketones, carbocyclic and carbonic acid derivatives, sulfonate esters, sulfonyl halides and vinyl sulfonyl ethers, active halogen compounds, epoxy compounds, azirid
- Red-sensitive internal image gelatin-silver chlorobromide emulsion (171 mg. gelatin/ft and 110 mg. silverlft cyan image transfer coupler l-hydroxy- 4- ⁇ 4-[a -(3-pentadecylphenoxy(butyramido]phenoxy ⁇ -N-ethyl-3',5-dicarboxy-2-naphthanilide (120 mg/ft and a foggingagent formyl-4-methylphenylhydrazine (0.5 g/mole of silver chlorobromide) 2.
- a scavenger interlayer comprising l-hydroxy-N- [a-(2,4-di-tert arnylphenoxy)butyl]-2-naphthamide (45 mglft tri-cresyl phosphate (23 mg/ft) and gelatin (65 mglft 3. Green-sensitive internal image silver chlorobromide emulsion (116 rng. gelatin/f9 and 100 mg.
- a scavenger and a yellow filter layer comprising 1- hydroxy-N-[a-(2,4-di-tert-amylphenoxy)butyl]-2 'naphthamide (-50 mg/ft), tri-cresyl phosphate (25 mg/ft"), yellow Carey Lea silver l5 mg/ft and gelatin (65 mglft 5.
- Two samples of the photosensitive element are exposed to a graduated-density multicolor test object.
- the following processing composition is employed in a pod and is spread between the exposed surface of the photosensitive element and each superposed dye image-receiving element by passing the transfer sandwich" between a pair of juxtaposed pressure rollers:
- a multilayer, multicolor photosensitive element is prepared according to the procedure described in Example 1 except that a blue sensitive gelatin-silver chlorobromide emulsion (126 mg gelatin/ft and mg silverlft is substituted for the silver chlorobromoiodide emulsion in layer 5 of Example 1.
- a multilayer dye image-receiving element is prepared by coating the following layers in the order recited on an opaque cellulose acetate film support:
- Example II Two samples of the photosensitive element are exposed and processed as in Example I.
- the elements are oven-tested as in Example l and then the background densities measured.
- the background density of the dye image-receiving element of the invention is 60 percent less than the background density observed with the control dye image-receiving element which does not contain the developer scavenger layer.
- Example 2 The procedure as described in Example 2 is followed with the exception that layers 1 and 2 of the dye imagereceiving layer are combined into a single 'layer.
- the background density of the dye image-receiving elements of the invention after 24 hrs. at 60C./70% R.H. is 64 percent less than the background density observed with a dye image-receiving element of the same configuration, but without the isocyanate-bisulfite adduct scavenger layer.
- a rupturable container containing an alkaline processing composition and which is adapted to be positioned during processing of said film unit so that a compressive force applied to said container by said pressure-applying members will effect a discharge of the containers contents within said film unit;
- said film unit containing an aromatic primary amino color developing agent; the improvement comprising employing a developing agent scavenger layer comprising an isocyanate-bisulfite addition product in a polymeric binder, said isocyanate-bisulfite addition product having the formula:
- M represents an alkali metal ion.
- the film unit of claim 4 which contains a timing layer between said scavenger layer and said dye imagereceiving layer.
- each-said nondiffusible coupler having the formula DYE LINK (COUP BALL) BALL LINK (COUP SOL) group consisting of a S-pyrazolone coupler radical, a pyrazolotriazole coupler radical, a phenolic coupler radical and an open-chain ketomethylene coupler radical, said COUP being substituted in the coupling position with said LINK;
- BALL is a photographically inert organic ballasting radical of such molecular size and configuration as to render said coupler nondiffusible during development in said alkaline processing composition;
- n is an integer of l to 2 when said LINK is an alkylidene radical, and n is I when said LINK is a radical selected from the group consisting of an azo radical, a mercuri radical, an oxy radical, a thio radical, a dithio radical and an azoxy radical;
- a dye image-receiving element comprising a support having thereon a dye image-receiving layer, said element being adapted to be superposed over said blue-sensitive silver halide emulsion layer after exposure of said photosensitive element;
- a rupturable container containing an alkaline processing composition and which is adapted to be positioned during processing of said film unit so that a compressive force applied to said container by said pressure'applying members will effect a discharge of the containers contents between said dye image-receiving layer and said blue-sensitive silver halide emulsion layer of said photosensitive element; said film unit containing an aromatic primaryamino color developing agent; the improvement comprising employing between said dye image-receiving layer and its said support a developing agent scavenger layer comprising an isocyanate-bisulfite addition product in a polymeric binder, said isocyanate-bisulfite addition product having the formula:
- a developing agent scavenger layer comprising an isocyanatebisulfite addition product in a polymeric binder, said isocyanate-bisulfite addition product having the formula:
- R represents an acyclic alkyl group, an alke- Posed photosensitive element and Said y image nyl group, an alicyclic group, or an aryl group; receiving y and R represents a hydrogen atom or an alkyl group; and Q p y a Compressive force to Said container to M represents an alkali metal i effect a discharge of the containers contents 5 between said outermost layer of said exposed 13.
- said treatment h t iti element d id d i i step B) is effected by ing layer.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10628171A | 1971-01-13 | 1971-01-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3725063A true US3725063A (en) | 1973-04-03 |
Family
ID=22310562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00106281A Expired - Lifetime US3725063A (en) | 1971-01-13 | 1971-01-13 | Developer scavengers for image transfer systems |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3725063A (enrdf_load_stackoverflow) |
| BE (1) | BE777782A (enrdf_load_stackoverflow) |
| CA (1) | CA982394A (enrdf_load_stackoverflow) |
| DE (1) | DE2201392A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2121553B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1376234A (enrdf_load_stackoverflow) |
| IT (1) | IT946557B (enrdf_load_stackoverflow) |
| NL (1) | NL7200475A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4069048A (en) * | 1975-02-17 | 1978-01-17 | Fuji Photo Film Co., Ltd. | Diffusion transfer photographic materials with color developer scavenger |
| US5047315A (en) * | 1987-09-11 | 1991-09-10 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US5098805A (en) * | 1987-01-28 | 1992-03-24 | Fuji Photo Film Co., Ltd. | Color photographs, a process for preparing them and color photographic material employed therefor |
| US5176989A (en) * | 1987-09-11 | 1993-01-05 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US5242785A (en) * | 1987-06-25 | 1993-09-07 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material containing color stain inhibitors and discoloring inhibitors |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3445228A (en) * | 1966-06-14 | 1969-05-20 | Eastman Kodak Co | Dye diffusion transfer process and element |
-
1971
- 1971-01-13 US US00106281A patent/US3725063A/en not_active Expired - Lifetime
- 1971-12-06 CA CA129,386A patent/CA982394A/en not_active Expired
-
1972
- 1972-01-04 FR FR7200083A patent/FR2121553B1/fr not_active Expired
- 1972-01-06 BE BE777782A patent/BE777782A/xx unknown
- 1972-01-12 GB GB146272A patent/GB1376234A/en not_active Expired
- 1972-01-12 NL NL7200475A patent/NL7200475A/xx unknown
- 1972-01-13 IT IT19343/72A patent/IT946557B/it active
- 1972-01-13 DE DE19722201392 patent/DE2201392A1/de active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3445228A (en) * | 1966-06-14 | 1969-05-20 | Eastman Kodak Co | Dye diffusion transfer process and element |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4069048A (en) * | 1975-02-17 | 1978-01-17 | Fuji Photo Film Co., Ltd. | Diffusion transfer photographic materials with color developer scavenger |
| US5098805A (en) * | 1987-01-28 | 1992-03-24 | Fuji Photo Film Co., Ltd. | Color photographs, a process for preparing them and color photographic material employed therefor |
| US5242785A (en) * | 1987-06-25 | 1993-09-07 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material containing color stain inhibitors and discoloring inhibitors |
| US5047315A (en) * | 1987-09-11 | 1991-09-10 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US5176989A (en) * | 1987-09-11 | 1993-01-05 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
Also Published As
| Publication number | Publication date |
|---|---|
| BE777782A (fr) | 1972-07-06 |
| NL7200475A (enrdf_load_stackoverflow) | 1972-07-17 |
| FR2121553A1 (enrdf_load_stackoverflow) | 1972-08-25 |
| GB1376234A (en) | 1974-12-04 |
| FR2121553B1 (enrdf_load_stackoverflow) | 1974-09-13 |
| CA982394A (en) | 1976-01-27 |
| DE2201392A1 (de) | 1972-07-27 |
| IT946557B (it) | 1973-05-21 |
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