BE664221A - - Google Patents

Info

Publication number

BE664221A

BE664221A BE664221A BE664221A BE664221A BE 664221 A BE664221 A BE 664221A BE 664221 A BE664221 A BE 664221A BE 664221 A BE664221 A BE 664221A BE 664221 A BE664221 A BE 664221A

Authority

BE

Belgium

Prior art keywords

coupler

oxo

pyrazoline

phenyl

sensitive material

Prior art date

1965-05-20

Links

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• 150000001875 compounds Chemical class 0.000 claims description 37
• 239000000463 material Substances 0.000 claims description 23
• -1 phenylazo Chemical group 0.000 claims description 19
• 239000000839 emulsion Substances 0.000 claims description 9
• ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 claims description 3
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• 125000000217 alkyl group Chemical group 0.000 claims description 2
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
• 229910006069 SO3H Inorganic materials 0.000 claims 1
• 125000004432 carbon atom Chemical group C* 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
• 239000000243 solution Substances 0.000 description 29
• 230000015572 biosynthetic process Effects 0.000 description 28
• 238000003786 synthesis reaction Methods 0.000 description 28
• 239000000047 product Substances 0.000 description 15
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
• 239000013078 crystal Substances 0.000 description 11
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• 125000001424 substituent group Chemical group 0.000 description 9
• 238000010168 coupling process Methods 0.000 description 7
• 238000005859 coupling reaction Methods 0.000 description 7
• 238000002844 melting Methods 0.000 description 7
• 230000008018 melting Effects 0.000 description 7
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 230000008878 coupling Effects 0.000 description 6
• 229960000583 acetic acid Drugs 0.000 description 5
• 239000012362 glacial acetic acid Substances 0.000 description 5
• 238000000034 method Methods 0.000 description 5
• 239000000203 mixture Substances 0.000 description 5
• BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 5
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
• 150000001412 amines Chemical class 0.000 description 4
• 239000007864 aqueous solution Substances 0.000 description 4
• 239000000975 dye Substances 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 230000008569 process Effects 0.000 description 4
• JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 4
• 229910052709 silver Inorganic materials 0.000 description 4
• 239000004332 silver Substances 0.000 description 4
• FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
• 239000002253 acid Substances 0.000 description 3
• 150000008064 anhydrides Chemical class 0.000 description 3
• 238000004061 bleaching Methods 0.000 description 3
• 238000009792 diffusion process Methods 0.000 description 3
• 238000001035 drying Methods 0.000 description 3
• 229940014800 succinic anhydride Drugs 0.000 description 3
• CJAJEZSCULAKCB-UHFFFAOYSA-N 2-sulfohexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(C(O)=O)S(O)(=O)=O CJAJEZSCULAKCB-UHFFFAOYSA-N 0.000 description 2
• XQITUXIEASXIMZ-UHFFFAOYSA-N 2-sulfooctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)S(O)(=O)=O XQITUXIEASXIMZ-UHFFFAOYSA-N 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• 238000010521 absorption reaction Methods 0.000 description 2
• 239000012670 alkaline solution Substances 0.000 description 2
• 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 2
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 2
• 229940005991 chloric acid Drugs 0.000 description 2
• 230000027326 copulation Effects 0.000 description 2
• 239000012954 diazonium Substances 0.000 description 2
• YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
• 239000000706 filtrate Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 125000001183 hydrocarbyl group Chemical group 0.000 description 2
• 230000003647 oxidation Effects 0.000 description 2
• 238000007254 oxidation reaction Methods 0.000 description 2
• 150000004989 p-phenylenediamines Chemical class 0.000 description 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
• DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 235000011121 sodium hydroxide Nutrition 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
• PZUVAVMKCPNBQL-UHFFFAOYSA-N 2-[(4-methoxyphenyl)diazenyl]-4H-pyrazol-3-one Chemical compound COC1=CC=C(C=C1)N=NN1N=CCC1=O PZUVAVMKCPNBQL-UHFFFAOYSA-N 0.000 description 1
• UELIBMUMKLRTKJ-UHFFFAOYSA-N 3-amino-1,4-dihydropyrazol-5-one Chemical compound NC1=NNC(=O)C1 UELIBMUMKLRTKJ-UHFFFAOYSA-N 0.000 description 1
• NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
• KHXUUPPXJWVTHH-UHFFFAOYSA-M 4-methoxybenzenediazonium;chloride Chemical compound [Cl-].COC1=CC=C([N+]#N)C=C1 KHXUUPPXJWVTHH-UHFFFAOYSA-M 0.000 description 1
• LPOVZHYARSAVIZ-UHFFFAOYSA-N 5-amino-2-phenyl-4h-pyrazol-3-one Chemical compound O=C1CC(N)=NN1C1=CC=CC=C1 LPOVZHYARSAVIZ-UHFFFAOYSA-N 0.000 description 1
• 206010011878 Deafness Diseases 0.000 description 1
• 206010034972 Photosensitivity reaction Diseases 0.000 description 1
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
• 238000000862 absorption spectrum Methods 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 238000006149 azo coupling reaction Methods 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
• 239000003518 caustics Substances 0.000 description 1
• 239000003610 charcoal Substances 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 229920001577 copolymer Polymers 0.000 description 1
• 230000009849 deactivation Effects 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 230000007812 deficiency Effects 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 150000001989 diazonium salts Chemical class 0.000 description 1
• IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 230000006872 improvement Effects 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 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 1
• 239000011368 organic material Substances 0.000 description 1
• 230000036211 photosensitivity Effects 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 230000009467 reduction Effects 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 230000035945 sensitivity Effects 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 125000001174 sulfone group Chemical group 0.000 description 1
• 230000008961 swelling Effects 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 239000001043 yellow dye Substances 0.000 description 1