AT216885B

AT216885B -

Info

Publication number: AT216885B
Authority: AT; Austria
Prior art keywords: dihydrazones; solution; sep; color; formula
Prior art date: 1958-12-11

Application number

AT899359A

Other languages

German (de)

English (en)

Inventor

Walter Pueschel Dr.

Ottmar Wahl Dr.

Willibald Pelz Dr.

Hans Schellenberger Dr.

Karl Loeffler Dr.

Original Assignee

Agfa Aktiengesellschaft

Priority date

1958-12-11

Filing date

1959-12-11

Publication date

1961-08-25

1959-12-11 Application filed by Agfa Aktiengesellschaft filed Critical Agfa Aktiengesellschaft

1961-08-25 Application granted granted Critical

1961-08-25 Publication of AT216885B publication Critical patent/AT216885B/de

Links

238000000034 method Methods 0.000 claims description 26
229910052709 silver Inorganic materials 0.000 claims description 9
239000004332 silver Substances 0.000 claims description 9
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
239000000463 material Substances 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000004989 dicarbonyl group Chemical group 0.000 claims description 4
125000001033 ether group Chemical group 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
239000000243 solution Substances 0.000 description 39
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
150000001875 compounds Chemical class 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
239000000047 product Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
-1 sulfo, carboxy Chemical group 0.000 description 15
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 10
239000000975 dye Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
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 9
239000001632 sodium acetate Substances 0.000 description 9
235000017281 sodium acetate Nutrition 0.000 description 9
239000001043 yellow dye Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
230000008878 coupling Effects 0.000 description 7
238000010168 coupling process Methods 0.000 description 7
238000005859 coupling reaction Methods 0.000 description 7
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-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
229960000583 acetic acid Drugs 0.000 description 6
150000001989 diazonium salts Chemical class 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000012954 diazonium Substances 0.000 description 5
125000000623 heterocyclic group Chemical group 0.000 description 5
150000002429 hydrazines Chemical class 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 4
238000001816 cooling Methods 0.000 description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
QQOZTOOQEFSMPW-UHFFFAOYSA-N 5-hydrazinyl-2-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(NN)C=C1S(O)(=O)=O QQOZTOOQEFSMPW-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
238000004061 bleaching Methods 0.000 description 3
239000007844 bleaching agent Substances 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
238000011161 development Methods 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
229940015043 glyoxal Drugs 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
229940067157 phenylhydrazine Drugs 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
YUTFQTAITWWGFH-UHFFFAOYSA-N 1-(1-benzofuran-2-yl)ethanone Chemical compound C1=CC=C2OC(C(=O)C)=CC2=C1 YUTFQTAITWWGFH-UHFFFAOYSA-N 0.000 description 2
IOMZCWUHFGMSEJ-UHFFFAOYSA-N 4-(azaniumylamino)benzenesulfonate Chemical compound NNC1=CC=C(S(O)(=O)=O)C=C1 IOMZCWUHFGMSEJ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000001049 brown dye Substances 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000000084 colloidal system Substances 0.000 description 2
OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 2
125000005594 diketone group Chemical group 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000007857 hydrazones Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
230000000873 masking effect Effects 0.000 description 2
LTUGGBOPBQPPGK-UHFFFAOYSA-A octadecasodium;hexaphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LTUGGBOPBQPPGK-UHFFFAOYSA-A 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000001047 purple dye Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
235000010265 sodium sulphite Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
229950000244 sulfanilic acid Drugs 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UUISWLJHAJBRAA-UHFFFAOYSA-N 1-benzofuran-2,3-dione Chemical compound C1=CC=C2C(=O)C(=O)OC2=C1 UUISWLJHAJBRAA-UHFFFAOYSA-N 0.000 description 1
UHJKAFUVAZYHMM-UHFFFAOYSA-N 1-dodecyl-2-(4-hydrazinylphenyl)benzimidazole-5-sulfonic acid Chemical compound N(N)C1=CC=C(C=C1)C=1N(C2=C(N1)C=C(C=C2)S(=O)(=O)O)CCCCCCCCCCCC UHJKAFUVAZYHMM-UHFFFAOYSA-N 0.000 description 1
WBULCZWMWLOUQW-UHFFFAOYSA-N 10-methylundecylbenzene Chemical compound CC(C)CCCCCCCCCC1=CC=CC=C1 WBULCZWMWLOUQW-UHFFFAOYSA-N 0.000 description 1
ZZEKVROOOYDJSJ-UHFFFAOYSA-N 2-(3-hydrazinylphenyl)-1-octadecylbenzimidazole-5-sulfonic acid Chemical compound N(N)C=1C=C(C=CC1)C=1N(C2=C(N1)C=C(C=C2)S(=O)(=O)O)CCCCCCCCCCCCCCCCCC ZZEKVROOOYDJSJ-UHFFFAOYSA-N 0.000 description 1
LKNGUDUZJMPMPA-UHFFFAOYSA-N 2-chloro-9-methyl-1-phenyl-3-propyldecan-1-one Chemical compound CCCC(CCCCCC(C)C)C(C(=O)C1=CC=CC=C1)Cl LKNGUDUZJMPMPA-UHFFFAOYSA-N 0.000 description 1
ZDGHHRPKFCVOJL-UHFFFAOYSA-N 3-hydrazinylbenzenesulfonic acid Chemical compound NNC1=CC=CC(S(O)(=O)=O)=C1 ZDGHHRPKFCVOJL-UHFFFAOYSA-N 0.000 description 1
HYLOSPCJTPLXSF-UHFFFAOYSA-N 5-amino-2-anilinobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1NC1=CC=CC=C1 HYLOSPCJTPLXSF-UHFFFAOYSA-N 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-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
206010025476 Malabsorption Diseases 0.000 description 1
208000004155 Malabsorption Syndromes Diseases 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
XRCFXMGQEVUZFC-UHFFFAOYSA-N anisindione Chemical compound C1=CC(OC)=CC=C1C1C(=O)C2=CC=CC=C2C1=O XRCFXMGQEVUZFC-UHFFFAOYSA-N 0.000 description 1
229960002138 anisindione Drugs 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000005266 casting Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000012937 correction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
CIISBNCSMVCNIP-UHFFFAOYSA-N cyclopentane-1,2-dione Chemical compound O=C1CCCC1=O CIISBNCSMVCNIP-UHFFFAOYSA-N 0.000 description 1
DOBMPNYZJYQDGZ-UHFFFAOYSA-N dicoumarol Chemical compound C1=CC=CC2=C1OC(=O)C(CC=1C(OC3=CC=CC=C3C=1O)=O)=C2O DOBMPNYZJYQDGZ-UHFFFAOYSA-N 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000011475 lollipops Nutrition 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
238000003541 multi-stage reaction Methods 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000004989 p-phenylenediamines Chemical class 0.000 description 1
150000004031 phenylhydrazines Chemical class 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
238000012545 processing Methods 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000003696 stearoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1