US3737318A - Light-sensitive color photographic material - Google Patents
Light-sensitive color photographic material Download PDFInfo
- Publication number
- US3737318A US3737318A US00143240A US3737318DA US3737318A US 3737318 A US3737318 A US 3737318A US 00143240 A US00143240 A US 00143240A US 3737318D A US3737318D A US 3737318DA US 3737318 A US3737318 A US 3737318A
- Authority
- US
- United States
- Prior art keywords
- coupler
- light
- photographic material
- color photographic
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000463 material Substances 0.000 title abstract description 25
- -1 SILVER HALIDE Chemical class 0.000 abstract description 19
- 229910052709 silver Inorganic materials 0.000 abstract description 13
- 239000004332 silver Substances 0.000 abstract description 13
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical group [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 11
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 6
- 108010010803 Gelatin Proteins 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 239000008273 gelatin Substances 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 235000011852 gelatine desserts Nutrition 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- RISYVLILTAVNNP-UHFFFAOYSA-N 2-dodecoxyphenol Chemical compound CCCCCCCCCCCCOC1=CC=CC=C1O RISYVLILTAVNNP-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- GIXSFSVVKULPEK-UHFFFAOYSA-N 2,4-dichloro-3-methylphenol Chemical compound CC1=C(Cl)C=CC(O)=C1Cl GIXSFSVVKULPEK-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- NOJIVXPLDDHVSU-UHFFFAOYSA-N 2-decoxyphenol Chemical compound CCCCCCCCCCOC1=CC=CC=C1O NOJIVXPLDDHVSU-UHFFFAOYSA-N 0.000 description 2
- NRGWEZIVWKLWTO-UHFFFAOYSA-N 2-hexadecoxyphenol Chemical compound CCCCCCCCCCCCCCCCOC1=CC=CC=C1O NRGWEZIVWKLWTO-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- IWNXSYOIVWMSLX-UHFFFAOYSA-N 2-octadecoxyphenol Chemical compound CCCCCCCCCCCCCCCCCCOC1=CC=CC=C1O IWNXSYOIVWMSLX-UHFFFAOYSA-N 0.000 description 2
- ITKQCIBIWWMFPM-UHFFFAOYSA-N 2-octoxyphenol Chemical compound CCCCCCCCOC1=CC=CC=C1O ITKQCIBIWWMFPM-UHFFFAOYSA-N 0.000 description 2
- WOQNPOAPKYFGMB-UHFFFAOYSA-N 2-tetradecoxyphenol Chemical compound CCCCCCCCCCCCCCOC1=CC=CC=C1O WOQNPOAPKYFGMB-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-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
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 229910001864 baryta Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- 229940080818 propionamide Drugs 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- NXVHEHXRZVQDCR-UHFFFAOYSA-N 1-n,1-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1C NXVHEHXRZVQDCR-UHFFFAOYSA-N 0.000 description 1
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 1
- YFCYICCDYAVMQP-UHFFFAOYSA-N 2-(2-octadecoxyphenoxy)acetic acid Chemical compound C(CCCCCCCCCCCCCCCCC)OC1=C(OCC(=O)O)C=CC=C1 YFCYICCDYAVMQP-UHFFFAOYSA-N 0.000 description 1
- AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical compound NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- XYXNTHIYBIDHGM-UHFFFAOYSA-N ammonium thiosulfate Chemical compound [NH4+].[NH4+].[O-]S([O-])(=O)=S XYXNTHIYBIDHGM-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 239000000298 carbocyanine 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
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000005457 ice water Substances 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
- 239000010446 mirabilite Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical compound [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
- 229940043349 potassium metabisulfite Drugs 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/34—Couplers containing phenols
- G03C7/346—Phenolic couplers
Definitions
- R is a hydrogen atom or a lower alkyl group; R is an aliphatic hydrocarbon residue having 8 to '18 carbon atoms; 11 is zero or 1; and m is zero or 1.
- This invention relates to a light-sensitive color photographic material. More particularly, the invention is concerned with a color photographic material containing a blue image-forming novel coupler belonging to the socalled protect type coupler, i.e. a Water-insoluble or difficultly water-soluble coupler to be used by dissolving the same in a diflicultly water-miscible high boiling solvent and dispersing the resulting solution in a photographic emulsion.
- the novel coupler is represented by the general formula,
- R is a hydrogen atom or a lower alkyl group
- R is an aliphatic hydrocarbon residue having 8 to 18 carbon atoms
- m is zero or 1
- n is zero or 1. 7
- the coupler of the present invention is quite useful as a protect type coupler, and has greatly overcome the drawbacks of known couplers. Accordingly, the light-sesitive color photographic material according to the present invention, which has been incorporated with the said coupler, is excellent in spectral absorption characteristic and can give a high densitv color 15 image excellent in transparency.
- the coupler used in the present invention is synthesized, for example, in the following manner:
- a long chain alkyl bromide and catechol are condensed with each other in dimethylformamide in the presence of potassium bicarbonate to form a catechol monoalkyl ether, which is then condensed with a halogenated fatty acid to obtain a long chain alkoxyphenoxy fatty acid.
- This acid is treated with phosphorus pentachloride to form an acid chloride, which is then condensed with a phenol derivative having an amino group in the o-position to synthesize the desired coupler.
- couplers represented by the general formula are set forth below, but couplers usable in the present invention are not limited only to these.
- catechol monododecyl ether B.P. 203-205 C./ 4 mm. Hg
- catechol monooctyl ether B.P. l183 C./4 mm. Hg
- catechol decyl ether B.P. 192-195 C./4 mm. Hg
- catechol tetradecyl ether B.P. 220-225 C./4 mm. Hg
- catechol octadecyl ether B.P. 230-235" C./3 mm. Hg.
- Tables 1 and 2 show the fact that the couplers used in the present invention have a low melting point and have excellent solubility in a high boiling solvent as compared with known couplers.
- the exemplified coupler (4) and know couplers were individually treated in the same manner as in Example 2 mentioned later, and the resulting color images were subjected to heat resistance test (at 77 C. for 2 days) and light resistance test (irradiation with an arc-lamp for 32 hours) to obtain such results as set forth in Table 3, in which the heat and light resistance values are residual color ratios at a density of 1.0.
- the couplers used in the present invention are not only low in melting point but also excellent in solubility in high boiling solvents and particularly high in durability of resulting color images as compared with known couplers, and hence are extremely useful as protect type couplers.
- the couplers used in the present invention into a light-sensitive color photographic material, there may be adopted any of the known procedures.
- the couplers are dissolved either singly or in combination of 2 or more in a high boiling solvent (B.P. 175 C. or more) such as tricrcsyl phosphate or dibutyl phthalate, or a low boiling solvent such as butyl acetate or butyl propionate, or a mixture of said solvents.
- a high boiling solvent such as tricrcsyl phosphate or dibutyl phthalate, or a low boiling solvent such as butyl acetate or butyl propionate, or a mixture of said solvents.
- This solution is mixed with an aqueous gelatin solutioucontaining a surface active agent and then emulsified by means of a high speed rotary mixer or a colloid mill.
- the emulsified liquid is added directly to a silver halide photographic emulsion, which is then coated on a support such as a glass plate, synthetic resin sheet, film ing aids, etc.
- a support such as a glass plate, synthetic resin sheet, film ing aids, etc.
- the emulsion may contain a known carbocyanine or merocyanine dye as an optical sensitizer therefor.
- the thus obtained light-sensitive color photographic material is exposed to radioactive rays such as a-rays or S-rays, visible rays or infrared rays, developed with a 5 developer containing a p-phenylenediamine type developing agents as an active ingredient, and then bleached, desilvered and fixed to obtain a-high density color.
- radioactive rays such as a-rays or S-rays, visible rays or infrared rays
- a 5 developer containing a p-phenylenediamine type developing agents as an active ingredient
- a color photographic material using the coupler of the present inventionrnay be incorporated with an UV- absorber of the benzophenorie t'ype (e.-g. 2-hydroxy-4- dodecyloxybenzophenone) or the triazole type [c.g. 2(2'- hydroxy-3,5'-di-tcrt-butylphenyl) benzotriazole], whereby the resulting image can further be increased in durabilityl base, baryta paper or laminated paper, followed by dryethyl N B methanesulfonamidoethyl y ing, to prepare a light-sensitive color photographiiunaie-w rial.
- an UV- absorber of the benzophenorie t'ype e.-g. 2-hydroxy-4- dodecyloxybenzophenone
- the triazole type c.g. 2(2'- hydroxy-3,5'-di-tcrt-butylphenyl) be
- the above-mentioned emulsified liquid is once set, finely cut, freed from the low boiling solvent by water-washing or the like means and added to a photo- .ra a acaail heaelinthyl.eliehytlmxr hxl.aparhenyla enediamine, N ethyl N hydroxyethyl 2 methyl-pphenylenediamine and N,N diethyl 2 methyl-p-phenylenediamine.
- the developer may contain a developgraphic emulsion, which is then coated on a support such mam-Controlling agent, -8- citralinic acid, in addition to as mentioned above, followed by drying, to prepare a lightsensitive color photographic material.
- a developgraphic emulsion which is then coated on a support such mam-Controlling agent, -8- citralinic acid, in addition to as mentioned above, followed by drying, to prepare a lightsensitive color photographic material.
- T The above-mentioned procedures are illustrative and are not limitative.
- the coupler may be incorporated into 2 or more different emulsion layers of a multi-layered color photo- 65 graphic material.
- the photographic emulsion used in the present invention may be prepared by use of various silver halides such as silver chloride, silver iodobromide or silver chlorobromide,
- the emulsion may have been incorporated with any of ordinary photographic additives such as, for example, anti-foggants, stabilizers,
- the material was subjected to ordinary stopping, film-hardening and water-washing treatments, and then subjected to second exposure by use of a white Water to make 1,000 ml.
- a light-sensitive silver halide color photographic material characterized by containing as a coupler a comlight. Subsequently, the thus treated material was depound f h general f la,
- a mixture comprising 10 g. of the exemplified coupler (4) and ml. of dibutyl phthalate was heated to 50 C. to form a solution.
- This solution was mixed with 5 ml. of a 10% aqueous Alkanol B solution and 200 ml. of a 5% aqueous gelatin solution, and the resulting mixture was subjected several times to a colloid mill to form a dispersion.
- This dispersion was added to 500 g. of a gelatin silver chlorobromide emulsion, which was then coated on a baryta paper and dried to prepare a light-sensitive material.
- N-ethyl-N-B methanesulfonamidoethyl-3-methyl- N ethyl N p-methanesulfonamidoethyl-3-methyl- Water to make 1,000 mil.
- the developed material was then dipped for 2 to 4 minutes in a stopping-fixing bath of the following composition:
- R is a hydrogen atom or a lower alkyl group; R is an aliphatic hydrocarbon residue having 8 to 18 carbon atoms; n is zero or 1; and m is zero or 1.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45040491A JPS4916056B1 (enrdf_load_stackoverflow) | 1970-05-14 | 1970-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3737318A true US3737318A (en) | 1973-06-05 |
Family
ID=12582035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00143240A Expired - Lifetime US3737318A (en) | 1970-05-14 | 1971-05-13 | Light-sensitive color photographic material |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3737318A (enrdf_load_stackoverflow) |
| JP (1) | JPS4916056B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1298305A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3891445A (en) * | 1973-06-20 | 1975-06-24 | Fuji Photo Film Co Ltd | Color photographic light-sensitive materials |
| WO2000066569A1 (fr) * | 1999-04-30 | 2000-11-09 | Ube Industries, Ltd. | Composes de benzoxazole, procede d'elaboration de ceux-ci et herbicides |
-
1970
- 1970-05-14 JP JP45040491A patent/JPS4916056B1/ja active Pending
-
1971
- 1971-05-13 US US00143240A patent/US3737318A/en not_active Expired - Lifetime
- 1971-05-14 GB GB05019/71A patent/GB1298305A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3891445A (en) * | 1973-06-20 | 1975-06-24 | Fuji Photo Film Co Ltd | Color photographic light-sensitive materials |
| WO2000066569A1 (fr) * | 1999-04-30 | 2000-11-09 | Ube Industries, Ltd. | Composes de benzoxazole, procede d'elaboration de ceux-ci et herbicides |
| US6706664B1 (en) | 1999-04-30 | 2004-03-16 | Ube Industries, Ltd. | Benzoxazole compounds, process for the preparation thereof and herbicides |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2123447B2 (de) | 1977-05-18 |
| JPS4916056B1 (enrdf_load_stackoverflow) | 1974-04-19 |
| DE2123447A1 (de) | 1971-12-02 |
| GB1298305A (en) | 1972-11-29 |
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