DE1544541A1 - Verfahren zur Herstellung von Disazofarbstoffen und deren Metallkomplexverbindungen - Google Patents
Verfahren zur Herstellung von Disazofarbstoffen und deren MetallkomplexverbindungenInfo
- Publication number
- DE1544541A1 DE1544541A1 DE19511544541 DE1544541A DE1544541A1 DE 1544541 A1 DE1544541 A1 DE 1544541A1 DE 19511544541 DE19511544541 DE 19511544541 DE 1544541 A DE1544541 A DE 1544541A DE 1544541 A1 DE1544541 A1 DE 1544541A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- formula
- parts
- dye
- azo
- 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.)
- Granted
Links
- 239000000975 dye Substances 0.000 title claims description 63
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 26
- -1 metal complex compounds Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 12
- 230000008569 process Effects 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 31
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 11
- 238000001465 metallisation Methods 0.000 claims description 10
- 150000002790 naphthalenes Chemical class 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000004696 coordination complex Chemical class 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims description 3
- 238000012986 modification Methods 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000987 azo dye Substances 0.000 claims description 2
- 230000009918 complex formation Effects 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000005265 dialkylamine group Chemical group 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 150000001845 chromium compounds Chemical class 0.000 claims 1
- 150000001869 cobalt compounds Chemical class 0.000 claims 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 28
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 16
- 239000002253 acid Substances 0.000 description 14
- 239000001103 potassium chloride Substances 0.000 description 14
- 235000011164 potassium chloride Nutrition 0.000 description 14
- 229910000029 sodium carbonate Inorganic materials 0.000 description 14
- 230000008878 coupling Effects 0.000 description 13
- 238000010168 coupling process Methods 0.000 description 13
- 238000005859 coupling reaction Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- 229920000742 Cotton Polymers 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229910000365 copper sulfate Inorganic materials 0.000 description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229920003043 Cellulose fiber Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005108 dry cleaning Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- HIVUAOXLSJITPA-UHFFFAOYSA-N 2-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=C(S(O)(=O)=O)C(N)=CC=C21 HIVUAOXLSJITPA-UHFFFAOYSA-N 0.000 description 2
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 2
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 150000004699 copper complex Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 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 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- ZFRBZRZEKIOGQI-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=CC(O)=C2C(N)=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1 ZFRBZRZEKIOGQI-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LDZGISULMSUOIK-UHFFFAOYSA-L copper acetic acid sulfate Chemical compound S(=O)(=O)([O-])[O-].[Cu+2].C(C)(=O)O LDZGISULMSUOIK-UHFFFAOYSA-L 0.000 description 1
- 230000001335 demethylating effect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ZULLAVFVXBSWQQ-UHFFFAOYSA-N nitro hydrogen carbonate Chemical compound OC(=O)O[N+]([O-])=O ZULLAVFVXBSWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 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
- 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
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
-
- 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
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
- C09B31/061—Disazo dyes from a coupling component "C" containing a directive hydroxyl group containing acid groups, e.g. -CO2H, -SO3H, -PO3H2, -OSO3H, -OPO2H2; Salts thereof
-
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19511544541 DE1544541A1 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur Herstellung von Disazofarbstoffen und deren Metallkomplexverbindungen |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19511544541 DE1544541A1 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur Herstellung von Disazofarbstoffen und deren Metallkomplexverbindungen |
| DEF0047105 | 1965-09-07 | ||
| DE1966F0049022 DE1644155B2 (de) | 1965-09-07 | 1966-04-27 | Verfahren zur herstellung von disazofarbstoffen und deren metallkomplexverbindungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1544541A1 true DE1544541A1 (de) | 1970-04-02 |
| DE1544541B2 DE1544541B2 (enrdf_load_stackoverflow) | 1974-05-02 |
| DE1544541C3 DE1544541C3 (enrdf_load_stackoverflow) | 1975-01-02 |
Family
ID=27180780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19511544541 Granted DE1544541A1 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur Herstellung von Disazofarbstoffen und deren Metallkomplexverbindungen |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1544541A1 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2634497A1 (de) * | 1976-07-31 | 1978-03-02 | Bayer Ag | Reaktivfarbstoffe |
| WO2003104335A1 (de) * | 2002-06-11 | 2003-12-18 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Wasserlösliche faserreaktive disazofarbstoffe, verfahren zu ihrer herstellung und ihre verwndung |
-
1951
- 1951-01-28 DE DE19511544541 patent/DE1544541A1/de active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2634497A1 (de) * | 1976-07-31 | 1978-03-02 | Bayer Ag | Reaktivfarbstoffe |
| WO2003104335A1 (de) * | 2002-06-11 | 2003-12-18 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Wasserlösliche faserreaktive disazofarbstoffe, verfahren zu ihrer herstellung und ihre verwndung |
| US7132517B2 (en) | 2002-06-11 | 2006-11-07 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Water-soluble fiber-reactive disazo dyes, method for producing the same and the use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1544541B2 (enrdf_load_stackoverflow) | 1974-05-02 |
| DE1544541C3 (enrdf_load_stackoverflow) | 1975-01-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1544539C3 (de) | Metallkomplex-Disazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE1544538C3 (de) | Metallkomplex-Disazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung | |
| CH514660A (de) | Verfahren zur Herstellung von Disazofarbstoffen | |
| DE1644366B1 (de) | Verfahren zur Herstellung von metallhaltigen wasserloeslichen Pyrimidinreaktiv-Azofarbstoffen | |
| DE1544541A1 (de) | Verfahren zur Herstellung von Disazofarbstoffen und deren Metallkomplexverbindungen | |
| DE1644151C3 (de) | Wasserlösliche Monoazoreaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung zum Färben und Bedrucken von Wolle, Seide, Polyamid- und Cellulosefasern | |
| DE2049664A1 (de) | MetaUkomplexmonoazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE2047025C3 (de) | Wasserlösliche 1 zu 1-Kupferkomplex-Disazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben oder Bedrucken von nativen oder regenerierten Cellulosefaser«, Leder, Wolle, Seide, Polyamid- oder Polyurethanfasern | |
| DE1544564C3 (enrdf_load_stackoverflow) | ||
| DE1544555C3 (de) | Verfahren zur Herstellung von Kupfer-, Kobalt- und Chromkomplex-Disazofarbstoffen | |
| DE1544518C3 (de) | Verfahren zur Herstellung wasserlöslicher 1 zu i-Kupfer-,1 zu 2-Kobalt- oder 1 zu 2-Chromkomplex-Disazofarbstoffe und deren Verwendung | |
| DE1544564C (de) | Verfahren zur Herstellung von Metallkomplex-Disazofarbstoffen | |
| DE1904113B2 (de) | Faserreaktive, schwermetallhaltige Formazanfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung | |
| DE1544543C3 (de) | Wasserlösliche Metallkomplexazofarbstoffe, Verfahren zu ihrer Herstellung und ihrer Verwendung | |
| DE1544500B2 (de) | Metallhaltige disazoreaktivfarbstoffe und verfahren zu deren herstellung | |
| AT281220B (de) | Verfahren zur Herstellung von neuen, wasserlöslichen, faserreaktiven Phenylazo-phthalocyaninfarbstoffen | |
| DE1644155C3 (de) | Verfahren zur Herstellung von Disazofarbstoffen und deren Metallkomplexverbindungen | |
| DE1794222A1 (de) | Wasserloesliche Disazofarbstoffe und deren Metallkomplexverbindungen und Verfahren zu ihrer Herstellung | |
| CH513955A (de) | Verfahren zur Herstellung von Disazofarbstoffen | |
| DE2308068C3 (de) | Monoazo-Verblndungen, Verfahren zu deren Herstellung und Ihre Verwendung als Farbstoffe | |
| DE1258526B (de) | Verfahren zur Herstellung von faserreaktiven, metallfreien wasserloeslichen Azofarbstoffen | |
| DE2037256A1 (de) | Wasserlösliche Metallkomplex-disazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE2065646A1 (de) | Metallkomplexverbindungen von monoazofarbstoffen, verfahren zu ihrer herstellung und ihre verwendung | |
| DE1116846B (de) | Verfahren zur Herstellung von Disazofarbstoffen und deren Metallkomplexverbindungen | |
| DE1243802B (de) | Verfahren zur Herstellung von mindestens einen dihalogenierten Pyrimidinring enthaltenden wasserloeslichen Farbstoffen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |