US3535113A - Production of color masking images using p-phenylenediamine mask-forming compounds - Google Patents
Production of color masking images using p-phenylenediamine mask-forming compounds Download PDFInfo
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- US3535113A US3535113A US610023A US3535113DA US3535113A US 3535113 A US3535113 A US 3535113A US 610023 A US610023 A US 610023A US 3535113D A US3535113D A US 3535113DA US 3535113 A US3535113 A US 3535113A
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- 150000001875 compounds Chemical class 0.000 title description 29
- 230000000873 masking effect Effects 0.000 title description 11
- 238000004519 manufacturing process Methods 0.000 title description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 64
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 63
- -1 silver halide Chemical class 0.000 description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
- 239000000243 solution Substances 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 238000002844 melting Methods 0.000 description 33
- 230000008018 melting Effects 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- 239000000839 emulsion Substances 0.000 description 29
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 238000009740 moulding (composite fabrication) Methods 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000002244 precipitate Substances 0.000 description 24
- 239000000975 dye Substances 0.000 description 22
- 125000003118 aryl group Chemical group 0.000 description 21
- 229910052709 silver Inorganic materials 0.000 description 19
- 239000004332 silver Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 10
- 125000003710 aryl alkyl group Chemical group 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 238000001429 visible spectrum Methods 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000001632 sodium acetate Substances 0.000 description 7
- 235000017281 sodium acetate Nutrition 0.000 description 7
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000005691 oxidative coupling reaction Methods 0.000 description 6
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- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 235000011150 stannous chloride Nutrition 0.000 description 6
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000004061 bleaching Methods 0.000 description 5
- 239000000084 colloidal system Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical class O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- NYBKRNICRGLHMH-UHFFFAOYSA-M 2,5-dichlorobenzenediazonium;chloride Chemical compound [Cl-].ClC1=CC=C(Cl)C([N+]#N)=C1 NYBKRNICRGLHMH-UHFFFAOYSA-M 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 150000002828 nitro derivatives Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000027326 copulation Effects 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 150000004989 p-phenylenediamines Chemical class 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004133 Sodium thiosulphate Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- OIPQUBBCOVJSNS-UHFFFAOYSA-L bromo(iodo)silver Chemical compound Br[Ag]I OIPQUBBCOVJSNS-UHFFFAOYSA-L 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 125000004963 sulfonylalkyl group Chemical group 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
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- 239000000725 suspension Substances 0.000 description 2
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- MEQKSFQEPDRNEQ-UHFFFAOYSA-N 1-bromo-3-methoxy-5-nitrobenzene Chemical compound COC1=CC(Br)=CC([N+]([O-])=O)=C1 MEQKSFQEPDRNEQ-UHFFFAOYSA-N 0.000 description 1
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- VSRYYONYIUUFFY-UHFFFAOYSA-N 2,4-dimethyl-6-nitroaniline Chemical compound CC1=CC(C)=C(N)C([N+]([O-])=O)=C1 VSRYYONYIUUFFY-UHFFFAOYSA-N 0.000 description 1
- QYLWEPIKPMUYAW-UHFFFAOYSA-N 2-bromo-6-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC(Br)=C1N QYLWEPIKPMUYAW-UHFFFAOYSA-N 0.000 description 1
- HIMVDAUFQRCQFX-UHFFFAOYSA-N 2-chloro-1,5-dimethyl-3-nitrobenzene Chemical compound CC1=CC(C)=C(Cl)C([N+]([O-])=O)=C1 HIMVDAUFQRCQFX-UHFFFAOYSA-N 0.000 description 1
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- RVNUUWJGSOHMRR-UHFFFAOYSA-N 3,5-dibromoaniline Chemical compound NC1=CC(Br)=CC(Br)=C1 RVNUUWJGSOHMRR-UHFFFAOYSA-N 0.000 description 1
- FHUSNGUPJXGLPL-UHFFFAOYSA-N 3-bromo-5-methoxyaniline Chemical compound COC1=CC(N)=CC(Br)=C1 FHUSNGUPJXGLPL-UHFFFAOYSA-N 0.000 description 1
- YIZRPAWCIFTHNA-UHFFFAOYSA-N 3-bromo-5-methylaniline Chemical compound CC1=CC(N)=CC(Br)=C1 YIZRPAWCIFTHNA-UHFFFAOYSA-N 0.000 description 1
- XUZCJDBXXYJXDD-UHFFFAOYSA-N 3-chloro-5-methylaniline Chemical compound CC1=CC(N)=CC(Cl)=C1 XUZCJDBXXYJXDD-UHFFFAOYSA-N 0.000 description 1
- CTMKLSIFZNPXHA-UHFFFAOYSA-N 4-(2-piperidin-1-ylpiperazin-1-yl)morpholine Chemical compound C1CCCCN1C1N(N2CCOCC2)CCNC1 CTMKLSIFZNPXHA-UHFFFAOYSA-N 0.000 description 1
- QDSCDFKGUAONPC-UHFFFAOYSA-N 4-chloro-2-methyl-6-nitroaniline Chemical compound CC1=CC(Cl)=CC([N+]([O-])=O)=C1N QDSCDFKGUAONPC-UHFFFAOYSA-N 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
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- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229940050271 potassium alum Drugs 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical class *S(*)(=O)=O 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 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
- G03C7/18—Processes for the correction of the colour image in subtractive colour photography
Definitions
- the present invention relates to the production of photographic colour images, more particularly to a process of colour correction utilizing an integral masking procedure.
- the cyan dye which should absorb red light and transmit green and blue light, usually absorbs to a minor degree green and blue light together with a major amount of red light.
- the magenta dye which should absorb green light and transmit blue and red light, usually absorbs to a minor degree red and blue light together with a major amount of green light.
- the yellow dye which should absorb blue light and transmit green and red light, is usually satisfactory.
- the mask be integral with the coloured images.
- coloured mask images are automatically formed in photographic colour materials by the use of a coloured colour coupler absorbing light in the region of side-absorption of the dye formed with said colour coupler on colur development.
- the mask image is formed by the coloured colour coupler itself, which is left on the nonexposed areas after colour development.
- the colour coupler which is left, in the non-exposed areas after image-wise exposure and primary colour development of the silver halide emulsion layer is treated oxidatively in the presence of a so-called masking compound for coupling therewith so as to form a masking dyestuff.
- the oxidative treatment usually is carried out in a photographic bleaching bath, e.g. a potassium hexacyanoferrateflll) containing alkaline aqueous solution used for removing the silver metal formed by development.
- a photographic bleaching bath e.g. a potassium hexacyanoferrateflll
- a colour corrected image is formed in a photographic element comprising a silver halide emulsion layer and a colour coupler, e.g. a colour coupler for magenta of the pyrazolone type, which is reactive with the oxidation product of an aromatic amino developing agent to form by colour development a primary dye image, more particularly a magenta dye image which absorbs a major proportion of light in the green region of the visible spectrum, and undesirably absorbs a minor proportion of light in the blue region of the visible spectrum, by treating the exposed and colour-developed photographic element with an oxidizing solution, such as a photographic bleaching bath, in the presence of a compound which oxidatively couples with the residual colour coupler, whereby a secondary dye image is formed more particularly a yellow dye image, having a gradation opposite to that of said primary dye image, and absorbin glue light but transmitting substantially all the light in the green region of the visible spectrum.
- a colour coupler e.g. a colour coupler for magenta of the
- That object has been accomplished by forming a dye stuff substantially absorbing in the red region of the visible spectrum by the oxidative copulation of the colourless magenta-forming colour coupler of the pyrazolone type, which is left after the colour development with a compound corresponding to the following general formula:
- R represents a hydrogen atom, or a monovalent organic group such as an alkyl group, an aralkyl group or an aryl group, or a bivalent organic group linked to an ortho-atom of the aromatic group represented by A including these groups in substituted form:
- R represents a monovalent organic radical such as an alkyl group, an aralkyl group or an aryl group, or a bivalent organic group linked to an ortho-atom of the aromatic group represented by A, including these groups in substituted form,
- R repreesnts a.hydrogen atom, or a substituent which splits 01f by said oxidative copulation
- A represents an aromatic group, which in p-position to the group is substituted by the NHR group, and in the o-positions in respect of theNHR group is substituted with a substituent by which the NHR group is sterically hindered and A includes such an aromatic group which is still further substituted.
- Sterical hindrance lowers the reduction power of the aromatic phenylenediamine derivative to such an extent that it practically does no longer possess developing power for exposed silver halide.
- sterically hindering substituents are particularly mentioned a halogen atom, e.g., a chlorine atom or a bromine atom, an alkyl group, e.g.
- a methyl group an alkoxy group, e.g., a methoxy group or an ethoxy group, an acyl group, an acyl-substituted amino group, a sulphamyl group, a sulphonylalkyl group, a sulphonylaryl group, a sulpho group, or a carboxyl group.
- R -substituents which can split off by the said oxidative copulation, are particularly mentioned a sulphonylalkyl, group, a sulphonylaryl group, wherein the alkyl and aryl radical may be further substituted, a sulpho group, a carbamyl group, a halogen atom, a sulphomethyl ene group, a carboxymethylene group and a phosphonic acid-substituted methyl group.
- the aromatic group represented by A may be further substituted, e.g., with a halogen atom, a cyano group, a sulphamyl group, a carboxyl group, a sulpho group, an alkyl group, an aryl group, an aralkyl group or a cycloaliphatic group, or make part of a ring system comprising condensed rings selected from the group of aromatic, alicyclic, or heterocyclic rings, which may be further substituted.
- a halogen atom e.g., a cyano group, a sulphamyl group, a carboxyl group, a sulpho group, an alkyl group, an aryl group, an aralkyl group or a cycloaliphatic group, or make part of a ring system comprising condensed rings selected from the group of aromatic, alicyclic, or heterocyclic rings, which may be further substituted.
- R' represents a hydrogen atom or an organic radical, e.g., an alkyl group, an aralkyl group, or an aryl group, including these groups in substituted form,
- R represents an organic radical, eg an alkyl group, an aralkyl group, or an aryl group including these groups in substituted form, or R together with R' forms a nitrogen-containing nucleus, e.g., a piperidino, morpholino, piperazine or pyrazole ring, including such nuclei in substituted form,
- each of R' and R represents a sterically hindering substituent for the NH group, e.g., a halogen atom such as a chlorine atom, an alkyl-, alkoxy-, cyano-, acyl, acyl-substituted amino-, sulphamyl-, sulphonylalkyl-, sulphonylaryl-, sulpho-, or carboxyl groups,
- a halogen atom such as a chlorine atom, an alkyl-, alkoxy-, cyano-, acyl, acyl-substituted amino-, sulphamyl-, sulphonylalkyl-, sulphonylaryl-, sulpho-, or carboxyl groups
- each of R and R represents a hydrogen atom, or a substituent e.g., a halogen atom, a cyano radical, a sulfamyl radical, a carbamyl radical, an acyl radical, a sulpho radical, a carboxyl radical, an alkoxyl group, an alkyl group, an alicyclic group, an aralkyl group or an aryl group including these groups in substituted form,
- a substituent e.g., a halogen atom, a cyano radical, a sulfamyl radical, a carbamyl radical, an acyl radical, a sulpho radical, a carboxyl radical, an alkoxyl group, an alkyl group, an alicyclic group, an aralkyl group or an aryl group including these groups in substituted form,
- R together with R and/or R together with R forms an aromatic, a partly hydrogenated aromatic or heterocyclic condensed nucleus, including such nucleus in substituted form, or
- R together with R' form a condensed nitrogen-containr ing heterocyclic nucleus including such nucleus in substituted form, or
- R together with R form a condensed nitrogen containing hereto-cyclic nucleus including such nucleus in substituted form.
- said compounds contain a substituent making them fast to diffusion in photographic colloids so that they can be selectively incorporated into one silver halide emulsion layer of a photographic multilayer colour material.
- N Nll2 CII3-(CH2)J5 i 12.1 g. (0.01 mole) of 3,5-dimethylaniline, prepared according to A. Van Loon, Rec.Tr.Ch.Pays-Bas 79 (1960) 986, and 7 cc. of 98% formic acid are refluxed for minutes.
- the water formed is distilled under reduced pressure on an oil bath of 100 C.
- the residue is recrystallized from petroleum naphtha. Yield: 10.8 g. of 3,5-dimethylformanilide. Melting point: 74 C.
- the p-phenylenediamine derivatives yield a cyan mask dyestuff compensating for the unwanted side-absorption in the red region of the spectrum of the magenta dyestulf formed by colour development.
- the p-phenylenediamine derivatives described in the present invention when used in photographic colour materials are preferably incorporated into a light-sensitive silver halide emulsion layer containing a magenta-forming colour coupler of the pyrazolone type.
- the p-phenylenediamine derivatives forming a green mask may be used in combination with compounds forming a yellow mask, which compensates for the unwanted side-absorption in the blue of the primary magenta dyestufi formed on colour development.
- Colour couplers of the pyrazolone type which are particularly suitable for being used in a masking process according to the present invention are 3-acylaminopyrazolone compounds e.g. thos described in the Belgian patent specification 654,110 and UK. patent specification 1,007,847, the latter specification containing a detailed description of the preparation of such couplers.
- the mask-forming compound is incorporated into the light-sensitive silver halide emulsion layer containing the magenta-forming colour coupler in a form made fast to diifusion by the introduction in the structure of said compound of an aliphatic radical containing from 5 to 20 carbon atoms in straight line.
- the silver halide emulsion is prepared by means of the usual photographic colloids such as e.g. gelatin, polyvinyl alcohol, casein, zein, collodion or other natural or synthetic colloids.
- the silver halide emulsion can be coated on a support consisting of paper, glass, nitrocellulose, cellulose esters, such as cellulose triacetate, polyester, polystyrene or other natural or synthetic resins, and may form part of a photographic material with one or more silver halide emulsion layers.
- a multilayer photographic colour material usually comprises the following elements: a support, a red-sensitive emulsion layer having a cyan-forming colour coupler, a green-sensitive emulsion layer having a magenta-forming colour coupler and a blue-sensitive emulsion layer having a yellow-forming colour coupler.
- a yellow filter composed in most of the cases of a gelatin layer containing dispersed colloidal silver, located between the blue-sensitive emulsion layer and the green-sensitive emulsion layer.
- a photographic colour negative masked according to the present invention can be formed as follows: after exposure to a coloured original of a photographic material containing in a silver halide emulsion layer sensitive to green light a magenta-forming colour coupler of the pyrazolone type and a mask-forming compound according to the present invention, silver halide is reduced to silver at the exposed areas in a colourdeveloping bath containing an aromatic primary amino colour developing agent, which at the same time is oxidized. The oxidized developing agent reacts with the colour coupler and forms a dyestuff, the mask-forming compound according to the invention not being aifected.
- the photographic material is treated with an alkaline oxidizing bath, such as a photographic bleaching bath wherein the oxidative coupling of the mask-forming compound with the residual pyrazolone takes place. Thereupon the colour material is washed with water, fixed and dried.
- an alkaline oxidizing bath such as a photographic bleaching bath wherein the oxidative coupling of the mask-forming compound with the residual pyrazolone takes place.
- the colour material is washed with water, fixed and dried.
- N,N-dialkyl-pphenylenediamines such as N-N-diethyl-p-phenylenediamine and N,N-diethyl-Z-methyl-p-phenylenediamine
- derivatives thereof such as N,N-dialkyl-N -sulphomethylor N,N-dialkyl-N -carboxymethyl-p-phenylenediamine.
- EXAMPLE 1 225 g. of a photographic silver bromide iodide emulsion, prepared by means of 50 g. of silver nitrate and 80 gof gelatin pro kg., are melted at 40 C. with 150 cc. of water. To this emulsion are added successively:
- the material is washed for 5 minutes and fixed again for 5 minutes at 20 C. in a fixing bath of the following composition:
- EXAMPLE 2 225 g. of a photographic silver bromide iodide emulsion, prepared by means of g. of silver nitrate and g. of gelatin pro kg., are melted at 40 C. with cc. of water. To this emulsion are added successively:
- R is hydrogen, an alkyl group, an aralkyl group or an aryl
- R is an alkyl group, an aralkyl group, or an aryl group, or R together with R forms a nitrogen-containing heterocyclic nucleus
- R is hydrogen or a substituent splitting off by said coueach of R and R is a sterically hindering substituent for the NHR group
- each of R and R is hydrogen, or an aliphatic, alicyclic,
- R together with R and/or R together with R forms an aromatic, partly hydrogenated aromatic or heterocyclic condensed nucleus
- R toegther with R forms a condensed nitrogen-containing heterocyclic nucleus
- R together with R forms a condensed nitrogen-containing heterocyclic nucleus
- each of said sterically hindering substituents in the said mask-forming compound is a halogen atom, an alkyl group, an alkoxy group, an acyl group, an acyl-substituted amino group, sulfonyl, a sulfonyl-alkyl group, a sulfonylaryl group, sulpho, or carboxy in acid or salt form, and
- said substituent which splits off by said oxidative coupling is a sulfonylalkyl group, a sulfonylaryl group, sulpho, carbamyl, a halogen atom, sulfomethylene, carboxymeth ylene or phosphoric acid-substituted methyl.
- a color photographic element having superposed silver halide emulsion layers sensitive to different regions of the visible spectrum, at least one of said layers containing a color coupler for magenta of the pyrazolone type and in non-migratory state a mask-forming compound corresponding to the following general formula:
- R' is hydrogen, an alkyl group, or an aryl group
- R' is an alkyl group or an aryl group, or
- R is hydogen or a substituent splitting off by said coueach of R' and R is a sterically hindering substituent se ected from a halogen atom, an alkyl group, an alkoxy group, and
- each of R and R is hydrogen, an alkyl group, an alkoxy group or a halogen atom.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2241/66A GB1153561A (en) | 1966-01-18 | 1966-01-18 | Improvements relating to the Producion of Colour Images |
Publications (1)
Publication Number | Publication Date |
---|---|
US3535113A true US3535113A (en) | 1970-10-20 |
Family
ID=9736087
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US610023A Expired - Lifetime US3535113A (en) | 1966-01-18 | 1967-01-18 | Production of color masking images using p-phenylenediamine mask-forming compounds |
Country Status (6)
Country | Link |
---|---|
US (1) | US3535113A (id) |
BE (1) | BE692636A (id) |
DE (1) | DE1644046A1 (id) |
FR (1) | FR1508682A (id) |
GB (1) | GB1153561A (id) |
NL (1) | NL6700716A (id) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4066457A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Color developer for diffusion transfer |
US4066456A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Incorporated carboxy substituted p-phenylenediamine color developer |
EP0152274A2 (en) * | 1984-02-07 | 1985-08-21 | Kyowa Medex Co. Ltd. | Method for the determination of Leucine Aminopeptidase (LAP) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE786710A (fr) * | 1971-10-04 | 1973-01-25 | Bristol Myers Co | Composition pour la teinture du cheveu avec |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE519872A (id) * | 1952-05-13 | |||
US3028237A (en) * | 1957-04-26 | 1962-04-03 | Agfa Ag | Masking of cyan images in color photography |
-
1966
- 1966-01-18 GB GB2241/66A patent/GB1153561A/en not_active Expired
-
1967
- 1967-01-16 BE BE692636D patent/BE692636A/xx unknown
- 1967-01-17 FR FR91845A patent/FR1508682A/fr not_active Expired
- 1967-01-17 NL NL6700716A patent/NL6700716A/xx unknown
- 1967-01-18 US US610023A patent/US3535113A/en not_active Expired - Lifetime
- 1967-01-18 DE DE19671644046 patent/DE1644046A1/de active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE519872A (id) * | 1952-05-13 | |||
US3028237A (en) * | 1957-04-26 | 1962-04-03 | Agfa Ag | Masking of cyan images in color photography |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4066457A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Color developer for diffusion transfer |
US4066456A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Incorporated carboxy substituted p-phenylenediamine color developer |
EP0152274A2 (en) * | 1984-02-07 | 1985-08-21 | Kyowa Medex Co. Ltd. | Method for the determination of Leucine Aminopeptidase (LAP) |
EP0152274A3 (en) * | 1984-02-07 | 1989-10-11 | Kyowa Medex Co. Ltd. | Method for the determination of enzyme activity |
Also Published As
Publication number | Publication date |
---|---|
FR1508682A (fr) | 1968-01-05 |
NL6700716A (id) | 1967-03-28 |
BE692636A (id) | 1967-07-17 |
DE1644046A1 (de) | 1971-04-15 |
GB1153561A (en) | 1969-05-29 |
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