CH496069A - Verfahren zur Herstellung von Disazofarbstoffen - Google Patents
Verfahren zur Herstellung von DisazofarbstoffenInfo
- Publication number
- CH496069A CH496069A CH543868A CH543868A CH496069A CH 496069 A CH496069 A CH 496069A CH 543868 A CH543868 A CH 543868A CH 543868 A CH543868 A CH 543868A CH 496069 A CH496069 A CH 496069A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonic acid
- formula
- hydroxynaphthalene
- amino
- dyes
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 aminoazo compound Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 239000000203 mixture Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- HUYJTJXLNBOVFO-UHFFFAOYSA-N 7-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(O)=CC=C21 HUYJTJXLNBOVFO-UHFFFAOYSA-N 0.000 description 2
- IXAURHGJEKWORG-UHFFFAOYSA-N 8-benzamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C(C1=CC=CC=C1)(=O)NC1=CC=CC2=C(C=C(C=C12)S(=O)(=O)O)O IXAURHGJEKWORG-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 239000001046 green dye Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical group NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- CFNGPHJXXIIBGW-UHFFFAOYSA-N 2-acetamido-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=C(S(O)(=O)=O)C(NC(=O)C)=CC=C21 CFNGPHJXXIIBGW-UHFFFAOYSA-N 0.000 description 1
- MRWAXRFIAWHEHE-UHFFFAOYSA-N 2-amino-2-(3-methylphenoxy)ethanol Chemical compound NC(CO)OC1=CC=CC(=C1)C MRWAXRFIAWHEHE-UHFFFAOYSA-N 0.000 description 1
- PVNFREMKYYZXRT-UHFFFAOYSA-N 2-benzamido-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound C=1C=C2C(O)=CC(S(O)(=O)=O)=CC2=C(S(O)(=O)=O)C=1NC(=O)C1=CC=CC=C1 PVNFREMKYYZXRT-UHFFFAOYSA-N 0.000 description 1
- URNUWVIPNDXJGL-UHFFFAOYSA-N 2-chloro-1-(6-methoxy-2,2,4-trimethyl-3,4-dihydroquinolin-1-yl)ethanone Chemical compound ClCC(=O)N1C(C)(C)CC(C)C2=CC(OC)=CC=C21 URNUWVIPNDXJGL-UHFFFAOYSA-N 0.000 description 1
- SGBQUMZTGSQNAO-UHFFFAOYSA-N 2-hydroxynaphthalene-1-sulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(O)=CC=C21 SGBQUMZTGSQNAO-UHFFFAOYSA-N 0.000 description 1
- MFNHJKWEKXVQHR-UHFFFAOYSA-N 4-hydroxy-8-[(4-sulfobenzoyl)amino]naphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(O)=CC(S(O)(=O)=O)=CC2=C1NC(=O)C1=CC=C(S(O)(=O)=O)C=C1 MFNHJKWEKXVQHR-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical class NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- OXQJOAGKNHVOAI-UHFFFAOYSA-N 5-amino-6-methoxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=C(N)C(OC)=CC=C21 OXQJOAGKNHVOAI-UHFFFAOYSA-N 0.000 description 1
- YKVBYISUDGOVDM-UHFFFAOYSA-N 6-acetamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(NC(=O)C)=CC=C21 YKVBYISUDGOVDM-UHFFFAOYSA-N 0.000 description 1
- CSEAXHLRXLHMQU-UHFFFAOYSA-N 6-benzamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=C1NC(=O)C1=CC=CC=C1 CSEAXHLRXLHMQU-UHFFFAOYSA-N 0.000 description 1
- FDVUQFBYRBEWHJ-UHFFFAOYSA-N 6-hydroxynaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(O)=CC=C21 FDVUQFBYRBEWHJ-UHFFFAOYSA-N 0.000 description 1
- CWBJFAHPCUSERS-UHFFFAOYSA-N 7-[(2-chloroacetyl)amino]-4-hydroxynaphthalene-2-sulfonic acid Chemical compound ClCC(=O)NC1=CC=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 CWBJFAHPCUSERS-UHFFFAOYSA-N 0.000 description 1
- KKAMNIDZQVXDJV-UHFFFAOYSA-N 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NC(=O)C)=CC=C21 KKAMNIDZQVXDJV-UHFFFAOYSA-N 0.000 description 1
- FSPFRDRUCUDVJR-UHFFFAOYSA-N 8-[(2-chloroacetyl)amino]-4-hydroxynaphthalene-2-sulfonic acid Chemical compound ClCC(=O)NC1=CC=CC2=C(C=C(C=C12)S(=O)(=O)O)O FSPFRDRUCUDVJR-UHFFFAOYSA-N 0.000 description 1
- JHLSTODBISZUTL-UHFFFAOYSA-N 8-acetamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(NC(=O)C)=CC=CC2=C1O JHLSTODBISZUTL-UHFFFAOYSA-N 0.000 description 1
- JUMINRWBSYTVFG-UHFFFAOYSA-N 8-amino-7-ethoxynaphthalene-2-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=C(N)C(OCC)=CC=C21 JUMINRWBSYTVFG-UHFFFAOYSA-N 0.000 description 1
- WDCKALMBICTILQ-UHFFFAOYSA-N 8-amino-7-methoxynaphthalene-2-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=C(N)C(OC)=CC=C21 WDCKALMBICTILQ-UHFFFAOYSA-N 0.000 description 1
- ZPLBZGGKAUXTRT-UHFFFAOYSA-N 8-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(O)=CC=CC2=C1 ZPLBZGGKAUXTRT-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KMZMAHIJPOFKJV-UHFFFAOYSA-N C1(=CC=CC=C1)NC(NC1=CC=CC2=C(C=C(C=C12)S(=O)(=O)O)O)=O Chemical compound C1(=CC=CC=C1)NC(NC1=CC=CC2=C(C=C(C=C12)S(=O)(=O)O)O)=O KMZMAHIJPOFKJV-UHFFFAOYSA-N 0.000 description 1
- YMSIURMJHQXJDU-UHFFFAOYSA-N CCOCC(N)OC1=CC=CC=C1 Chemical compound CCOCC(N)OC1=CC=CC=C1 YMSIURMJHQXJDU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JLPNFQSZHUDDJA-UHFFFAOYSA-N NC(CO)OC1=CC=CC(=C1)O Chemical compound NC(CO)OC1=CC=CC(=C1)O JLPNFQSZHUDDJA-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000005615 azonium group Chemical group 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0052478 | 1967-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH496069A true CH496069A (de) | 1970-09-15 |
Family
ID=7105483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH543868A CH496069A (de) | 1967-05-22 | 1968-04-11 | Verfahren zur Herstellung von Disazofarbstoffen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE715439A (en:Method) |
| CH (1) | CH496069A (en:Method) |
| DE (1) | DE1644214A1 (en:Method) |
| FR (1) | FR1573145A (en:Method) |
| GB (1) | GB1176898A (en:Method) |
| NL (1) | NL6806855A (en:Method) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4002424A (en) * | 1973-06-14 | 1977-01-11 | E. I. Du Pont De Nemours And Company | Solution of isomer mixture of naphthylazophenylazonaphthyl disulfonate dye |
| EP0289458B1 (de) * | 1987-04-27 | 1994-02-02 | Ciba-Geigy Ag | Anionische Disazofarbstoffe |
| DE3725082A1 (de) * | 1987-07-29 | 1989-02-09 | Bayer Ag | Disazofarbstoffe |
| ES2081599T3 (es) * | 1991-12-20 | 1996-03-16 | Ciba Geigy Ag | Procedimiento para teñir o estampar materiales de fibra que contienen grupos hidroxilo. |
| DE59207127D1 (de) * | 1991-12-20 | 1996-10-17 | Ciba Geigy Ag | Verfahren zum Färben oder Bedrucken von hydroxylgruppenhaltigen Fasermaterialien |
-
1967
- 1967-05-22 DE DE19671644214 patent/DE1644214A1/de active Pending
-
1968
- 1968-04-11 CH CH543868A patent/CH496069A/de not_active IP Right Cessation
- 1968-05-14 GB GB2286468A patent/GB1176898A/en not_active Expired
- 1968-05-15 NL NL6806855A patent/NL6806855A/xx unknown
- 1968-05-20 BE BE715439D patent/BE715439A/xx unknown
- 1968-05-22 FR FR1573145D patent/FR1573145A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1573145A (en:Method) | 1969-07-04 |
| BE715439A (en:Method) | 1968-10-16 |
| DE1644214A1 (de) | 1970-12-17 |
| NL6806855A (en:Method) | 1968-11-25 |
| GB1176898A (en) | 1970-01-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE742517C (de) | Verfahren zur Herstellung von metallhaltigen Azofarbstoffen | |
| DE1289930B (de) | Verfahren zur Herstellung von Azofarbstoffen und deren Metallkomplexverbindungen | |
| DE1544539B2 (de) | .Metallkomplex-Disazoffarbstoffe und Verfahren zu ihrer Herstellung | |
| DE1795175C3 (de) | Wasserlösliche Disazofarbstoffe und ihre Verwendung | |
| CH496069A (de) | Verfahren zur Herstellung von Disazofarbstoffen | |
| DE1215282B (de) | Verfahren zur Herstellung von wasserloeslichen Disazofarbstoffen | |
| DE2154942B2 (de) | Faserreaktive Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von nativen oder regenerierten Cellulosefasern, natürlichen oder synthetischen Polyamidfasern oder von Polyurethanfasern | |
| DE1219155B (de) | Verfahren zur Herstellung wasserloeslicher Azofarbstoffe | |
| DE1218636B (de) | Verfahren zur Herstellung von wasserloeslichen Pyrimidinfarbstoffen | |
| DE2126299C3 (de) | Phenyl-naphthotrlazolmonoazofarbstoffe, deren Herstellung und Verwendung | |
| DE1098642B (de) | Verfahren zur Herstellung von kationischen Farbstoffen | |
| DE1225319B (de) | Verfahren zur Herstellung von Azofarbstoffen | |
| DE1544541C3 (en:Method) | ||
| CH515315A (de) | Verfahren zur Herstellung von faserreaktiven, schwermetallhaltigen Formazanfarbstoffen | |
| DE925539C (de) | Verfahren zur Herstellung neuer Trisazofarbstoffe | |
| CH515316A (de) | Verfahren zur Herstellung von faserreaktiven schwermetallhaltigen Formazanfarbstoffen | |
| CH615693A5 (en) | Process for preparing new trisazo dyes, the trisazo dyes and use thereof | |
| DE951527C (de) | Verfahren zur Herstellung von metallisierbaren Disazofarbstoffen | |
| AT220266B (de) | Verfahren zur Herstellung von neuen Imidazolium-Azofarbstoffen | |
| DE1964148C3 (de) | Chromhaltige Azo-Triazol-Komplexfarbstoffe und Verfahren zur Herstellung derselben und deren Verwendung | |
| AT162228B (de) | Verfahren zur Herstellung von neuen Monoazofarbstoffen | |
| DE1644087C3 (de) | Verfahren zur Herstellung wasserlöslicher organischer Reaktivfarbstoffe | |
| DE1794222A1 (de) | Wasserloesliche Disazofarbstoffe und deren Metallkomplexverbindungen und Verfahren zu ihrer Herstellung | |
| DE894294C (de) | Verfahren zur Herstellung von Monoazofarbstoffen der Pyrazolonreihe | |
| AT165077B (de) | Verfahren zur Herstellung neuer Trisazofarbstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |