DE1151891B - Process for the production of complex dyes containing chromium - Google Patents
Process for the production of complex dyes containing chromiumInfo
- Publication number
- DE1151891B DE1151891B DEB52653A DEB0052653A DE1151891B DE 1151891 B DE1151891 B DE 1151891B DE B52653 A DEB52653 A DE B52653A DE B0052653 A DEB0052653 A DE B0052653A DE 1151891 B DE1151891 B DE 1151891B
- Authority
- DE
- Germany
- Prior art keywords
- aromatic
- chromium
- amino
- sulfonic acid
- aldehydes
- 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.)
- Pending
Links
- 239000000975 dye Substances 0.000 title claims description 18
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 7
- 229910052804 chromium Inorganic materials 0.000 title claims description 7
- 239000011651 chromium Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 230000020176 deacylation Effects 0.000 claims description 2
- 238000005947 deacylation reaction Methods 0.000 claims description 2
- 230000020335 dealkylation Effects 0.000 claims description 2
- 238000006900 dealkylation reaction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- -1 1-Amino-2-hydroxybenzene-5-sulfonic acid-benzenesulfonic acid Chemical compound 0.000 description 5
- 210000002268 wool Anatomy 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- FABVMBDCVAJXMB-UHFFFAOYSA-N 3,5-dichloro-2-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=C(Cl)C=C1C=O FABVMBDCVAJXMB-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- LJAOOBNHPFKCDR-UHFFFAOYSA-K chromium(3+) trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Cr+3] LJAOOBNHPFKCDR-UHFFFAOYSA-K 0.000 description 2
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- OVQABVAKPIYHIG-UHFFFAOYSA-N n-(benzenesulfonyl)benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NS(=O)(=O)C1=CC=CC=C1 OVQABVAKPIYHIG-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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 1
- OQSRDROAXITENW-UHFFFAOYSA-N 4-acetamido-2,5-dimethoxybenzenesulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=C(OC)C=C1NC(C)=O OQSRDROAXITENW-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000002431 aminoalkoxy group Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 0.000 description 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 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
- C09B55/00—Azomethine dyes
- C09B55/002—Monoazomethine dyes
-
- 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
- C09B55/00—Azomethine dyes
- C09B55/001—Azomethine dyes forming a 1,2 complex metal compound, e.g. with Co or Cr, with an other dye, e.g. with an azo or azomethine dye
-
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur-HersteRun gf von chromhaltigen Komple--xfä-rbstöffe#ii--' Es wurde gefunden, daß man neue, wertvolle chromhaltige Komplexfarbstoffe erhält, wenn man chromabgebende Mittel auf die äquimolaren oder annähernd äquimolaren Gemische von aromatischen 1-Amino-2-hydroxy- oder -alkoxyverbindungen Lind aro.matischen 2-Hydroxyaldehyden oder auf die daraus erhaltenen Azomethine einwirken läßt und die aromatischen Amine bzw. die aromatischen Aldehyde so wählt, daß der gebildete Komplexfarbstoff eine Gruppe der allgemeinen Formel -SO,-NH-S0,-R enthält, in der R einen gegebenenfalls substituierten Rest des Benzols oder Naphthalins bedeutet.PROCESS FOR THE MANUFACTURING OF COMPLETE COMPLETE CHROMED FUEL # ii-- ' It has been found that new, valuable chromium-containing complex dyes are obtained, when using chromium donors on the equimolar or near equimolar mixtures of aromatic 1-amino-2-hydroxy or alkoxy compounds and aromatic 2-Hydroxyaldehydes or the azomethines obtained therefrom can act and selects the aromatic amines or the aromatic aldehydes so that the formed Complex dye contains a group of the general formula -SO, -NH-S0, -R in which R denotes an optionally substituted radical of benzene or naphthalene.
Aminokomponenten, die die Gruppe - SO, - NH - S02 - R enthalten, sind z. B. 1-Amino-2-hydroxybenzol-5-sulfonsäure-benzolsulfonsäureimid, 1-Amino-2-hydroxybenzol-5-sulfonsäure-4'-chlorbenzolsulfonsäureimid, 1 - Amino - 2 - hydroxy - 5- sulfonsäure - 2'- methylbenzolsulfonsäureimid, 1-Amino-2-hydroxybeiizol-5-sulfonsäure-3'-nitrobenzolsulfonsäureimid, 1-Amino-2-hydroxybenzol-5-sulfonsäure-iiaphthalin-(2)-sulfonsäureimid, 1-Amino-2-methoxybenzol-5-sulfonsäure-benzolsulfonsäureimid, 1-Amino-2-methoxy-5-methylbenzol-4-sulfonsäure-benzolsulfonsäureimid, 1-Amino-2-methoxy-5-methylbenzol-4-sulfonsäure-4'-chlorbenzolsulfonsäureimid, 1-Amino-2,5-dimethoxybenzol-4-sulfonsäure-benzolsulfonsäureimid und 1-Amino-2-äthoxynaphthalin-6-sulfonsäure-4'-methylbenzolsulfonsäureimid.Amino components which contain the group - SO, - NH - S02 - R are z. B. 1-Amino-2-hydroxybenzene-5-sulfonic acid-benzenesulfonic acid imide, 1-amino-2-hydroxybenzene-5-sulfonic acid-4'-chlorobenzenesulfonic acid imide, 1 - amino - 2 - hydroxy - 5- sulfonic acid - 2'-methylbenzenesulfonic acid imide, 1-Amino-2-hydroxybeiizole-5-sulfonic acid-3'-nitrobenzenesulfonic acid imide, 1-amino-2-hydroxybenzene-5-sulfonic acid-iiaphthalene- (2) -sulfonic acid imide, 1-amino-2-methoxybenzenes-5-sulfonic acid-benzenesulfonic acid imide , 1-Amino-2-methoxy-5-methylbenzene-4-sulfonic acid-benzenesulfonic acid imide, 1-amino-2-methoxy-5-methylbenzene-4-sulfonic acid-4'-chlorobenzenesulfonic acid imide, 1-amino-2,5-dimethoxybenzene- 4-sulfonic acid-benzenesulfonic acid imide and 1-amino-2-ethoxynaphthalene-6-sulfonic acid-4'-methylbenzenesulfonic acid imide.
Die Herstellung dieser Verbindungen ist im deutschen Patent 1 115 384 beschrieben.The preparation of these compounds is described in German Patent 1,115,384.
Die neuen chromhaltigen Komplexfarbstoffe erhält man aus den Azomethinen oder aus den äquimolaren oder annähernd äquimolaren Mischungen ihrer Komponenten durch Behandlung mit chromabgebenden Mitteln, wie Chromchlorid-Hexahydrat, Chromsulfat oder Chromformiat, in wäßriger Lösung oder Suspension oder in organischen Lösungsmitteln bei erhöhter Temperatur, gegebenenfalls unter erhöhtem Druck. An Stelle der genannten Aminohydroxy- bzw. Aminoalkoxyverbindungen können auch die entsprechenden Carbonsäureamide verwendet werden, da unter den Reaktionsbedingungen zugleich eine Entacylierung und eine Entalkylierung eintritt, ohne daß der Disulfimidrest abgespalten wird.The new chromium-containing complex dyes are obtained from the azomethines or from the equimolar or approximately equimolar mixtures of their components by treatment with chromium donating agents such as chromium chloride hexahydrate, chromium sulfate or chromium formate, in aqueous solution or suspension or in organic solvents at elevated temperature, optionally under elevated pressure. Instead of the mentioned Aminohydroxy or aminoalkoxy compounds can also be the corresponding carboxamides can be used because under the reaction conditions at the same time a deacylation and dealkylation occurs without the disulfimide radical being split off.
Die Chromkomplexfarbstoffe können aus den Umsetzungsgemischen vorteilhaft durch Zusatz von Aminen, wie Butylamin, Cyclohexylamin, Pyrrolidin und Aminobenzol, oder Älkylammoniunisalzeii, wie Trimethylbenzylammoniumchlorid, abgeschieden werden. Die gebildeten Farbstoffsalze sind in-organischen Lösungsmitteln und Kunststoffen leicht löslich. - Die neuen Farbstoffe eignen sich vorzüglich zum Färben von Wolle, Seide, Leder -und Gebi Iden aus synthetischen Polyamiden und -Polyurethanen. Gegenüber den entsprechenden, statt der Disulfonsäureimidgruppen Sulfonsäurereste enthaltenden Farbstoffen haben sie merklich bessere Naßechtheitseigenschaften.The chromium complex dyes can advantageously be deposited from the reaction mixtures by adding amines, such as butylamine, cyclohexylamine, pyrrolidine and aminobenzene, or alkylammonium salts, such as trimethylbenzylammonium chloride. The dye salts formed are easily soluble in organic solvents and plastics. - The new dyes are particularly suitable for dyeing wool, silk, leather and structures made of synthetic polyamides and polyurethanes. Compared to the corresponding dyes containing sulfonic acid radicals instead of the disulfonic acid imide groups, they have noticeably better wet fastness properties.
Die in den Beispielen genannten Teile sind Gewichtsteile.The parts mentioned in the examples are parts by weight.
Beispiel 1 19 Teile 1-Acetvlamino-2-methoxybenzol-5-sulfonsäure-benzolsulfonsäureimid, 8,5 Teile 2-Hydroxy-3,5-dichlorbenzaldehyd und 13,5 Teile Chromchlorid-Hexahydrat werden in 200 Teile Di-(2-hydroxyäth%!1)-äther eingetragen und die Mischung bei 125 bis 130'C so lange gerührt, bis sich der Metallkomplex vollständig gebildet hat. Die entstandene gelbbraune Lösung gießt man in 2000 Teile Wasser und scheidet den Farbstoff durch Zusatz von 10 Teilen Cyclohexylamin ab. Er stellt nach dem Trocknen ein gelbes Pulver dar, das sich leicht in heißem Wasser löst und Wolle aus stark saurem Bad in gelben Tönen sehr echt färbt.Example 1 19 parts of 1-acetylamino-2-methoxybenzene-5-sulfonic acid benzenesulfonic acid imide, 8.5 parts of 2-hydroxy-3,5-dichlorobenzaldehyde and 13.5 parts of chromium chloride hexahydrate are dissolved in 200 parts of di- (2-hydroxyeth% ! 1) ether entered and the mixture stirred at 125 to 130'C until the metal complex has been completely formed. The resulting yellow-brown solution is poured into 2000 parts of water and the dye is separated off by adding 10 parts of cyclohexylamine. After drying, it is a yellow powder that dissolves easily in hot water and dyes wool from a strongly acidic bath in yellow tones very realistically.
Auf die gleiche Weise erhält man Farbstoffe mit ähnlichen Eigenschaften
aus der Komponente der folgenden Tabelle:
Verwendet man als Aldehydkomponente 2-Hydroxybenzaldehyd oder 2-Hydroxynaphthaldehyd-(1), so erhält man Farbstoffe mit ähnlichen Eigenschaften.If the aldehyde component used is 2-hydroxybenzaldehyde or 2-hydroxynaphthaldehyde- (1), this gives dyes with similar properties.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB52653A DE1151891B (en) | 1959-03-28 | 1959-03-28 | Process for the production of complex dyes containing chromium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB52653A DE1151891B (en) | 1959-03-28 | 1959-03-28 | Process for the production of complex dyes containing chromium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1151891B true DE1151891B (en) | 1963-07-25 |
Family
ID=6969975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB52653A Pending DE1151891B (en) | 1959-03-28 | 1959-03-28 | Process for the production of complex dyes containing chromium |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1151891B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE846142C (en) * | 1950-06-30 | 1952-08-11 | Basf Ag | Process for the production of water-soluble chromium-containing dyes |
| DE925725C (en) * | 1953-01-14 | 1955-03-28 | Basf Ag | Process for the production of water-soluble chromium-containing dyes |
| DE1024653B (en) | 1954-02-18 | 1958-02-20 | Basf Ag | Process for the production of sulfonic acid group-free metal complex compounds of azomethine dyes |
-
1959
- 1959-03-28 DE DEB52653A patent/DE1151891B/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE846142C (en) * | 1950-06-30 | 1952-08-11 | Basf Ag | Process for the production of water-soluble chromium-containing dyes |
| DE925725C (en) * | 1953-01-14 | 1955-03-28 | Basf Ag | Process for the production of water-soluble chromium-containing dyes |
| DE1024653B (en) | 1954-02-18 | 1958-02-20 | Basf Ag | Process for the production of sulfonic acid group-free metal complex compounds of azomethine dyes |
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