DE1106013B - Process for the production of chromium complex dyes - Google Patents
Process for the production of chromium complex dyesInfo
- Publication number
- DE1106013B DE1106013B DEB51384A DEB0051384A DE1106013B DE 1106013 B DE1106013 B DE 1106013B DE B51384 A DEB51384 A DE B51384A DE B0051384 A DEB0051384 A DE B0051384A DE 1106013 B DE1106013 B DE 1106013B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- chromium
- chromium complex
- production
- complex dyes
- 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
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 11
- 229910052804 chromium Inorganic materials 0.000 title claims description 11
- 239000011651 chromium Substances 0.000 title claims description 11
- 239000000975 dye Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- 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
- 150000001875 compounds Chemical class 0.000 description 2
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
- IAOZVUUQCPRLOI-UHFFFAOYSA-N 3-amino-4-hydroxy-n-phenylbenzenesulfonamide Chemical compound C1=C(O)C(N)=CC(S(=O)(=O)NC=2C=CC=CC=2)=C1 IAOZVUUQCPRLOI-UHFFFAOYSA-N 0.000 description 1
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 1
- 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
- 229910021556 Chromium(III) chloride Inorganic materials 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 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
- 239000011636 chromium(III) chloride Substances 0.000 description 1
- 235000007831 chromium(III) chloride Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000002689 soil 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
- C09B45/00—Complex metal compounds of azo 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/01—Complex metal compounds of azo dyes characterised by the method of metallisation
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von Chromkomplexfarbstoffen Es wurde gefunden, daß man Chromkomplexfarbstoffe erhält, wenn man Arylazomalondialdehyde, die keine zur Komplexbildung befähigten Gruppen in 2-Stellung zur Azogruppe besitzen, mit chromabgebenden Mitteln in einem geeigneten Lösungsmittel im Molverhältnis 1 : 1 mit gegebenenfalls substituierten o-Aminophenolen kondensiert. Die entstehenden kationischen Chromkomplexverbindungen der wahrscheinlichen Formel in der die beiden Benzolkerne beliebig substituiert sein können und X einen anionischen Rest bedeutet, unterscheiden sich von den nach dem Patent 1047 964 durch 1 :2-Kondensation erhaltenen Chromkomplexfarbstoffen dadurch, daß sie auch aus stark saurem Bad in kräftigen Farbtönen auf Wolle ziehen. Gegenüber sonstigen 1 : 1-Chromkomplexfarbstoffen zeichnen sich die Farbstoffe durch ein besonders gutes Egalisiervermögen aus. Zum Teil ziehen sie auch auf Polyacrylnitril bzw. Leder auf.Process for the preparation of chromium complex dyestuffs It has been found that chromium complex dyestuffs are obtained if arylazomalondialdehydes which do not have any complexing groups in the 2-position to the azo group, with chromium donating agents in a suitable solvent in a molar ratio of 1: 1 with optionally substituted o-aminophenols condensed. The resulting cationic chromium complex compounds of the likely formula in which the two benzene rings may be substituted as desired and X is an anionic radical, different from those according to patent 1,047,964 by 1: obtained 2-condensation chromium complex dyes in that they also pull out the strongly acidic bath in bright colors on wool. Compared to other 1: 1 chromium complex dyes, the dyes are distinguished by a particularly good leveling capacity. In some cases, they are also applied to polyacrylonitrile or leather.
Ihre Darstellung erfolgt am einfachsten in der Weise, daß man ein Gemisch aus dem betreffenden Arylazomalondialdehyd und dem o-Aminophenol in einem geeigneten Lösungsmittel mit einem chromabgebenden Mittel, z. B. Chrom(III)-chlorid, auf Temperaturen von 60 bis 130° C erhitzt. Sind die Komponenten genügend wasserlöslich, so gelingt die Chromierung z. B. auch mit Chromformiat in wäßrigem Medium.The easiest way to present them is to give one Mixture of the arylazomalondialdehyde in question and the o-aminophenol in one suitable solvent with a chromium donating agent, e.g. B. Chromium (III) chloride, heated to temperatures of 60 to 130 ° C. Are the components sufficiently soluble in water, so the chroming succeeds z. B. also with chromium formate in an aqueous medium.
Die in den Beispielen genannten Teile sind Gewichtsteile.The parts mentioned in the examples are parts by weight.
Beispiel 1 10 Teile Benzol-l-azomalondialdehyd-4-sulfonsäureamid und 6,5 Teile 1-Hydroxy-2-amino-4-nitrobenzol werden zusammen mit 15 Teilen Chrom(III)-chloridhexahydrat in 200 Teilen Dimethylformamid gelöst und unter Rühren 6 Stunden auf 100 bis 120° C erhitzt. Durch Abkühlen und Ausfällen mit Wasser erhält man 12 Teile eines Farbstoffs der wahrscheinlichen. Formel der aus schwefelsaurem Bad in braunen Tönen auf Wolle und Polyamidfasern zieht.Example 1 10 parts of benzene-1-azomalondialdehyde-4-sulfonic acid amide and 6.5 parts of 1-hydroxy-2-amino-4-nitrobenzene are dissolved together with 15 parts of chromium (III) chloride hexahydrate in 200 parts of dimethylformamide and stirred for 6 hours heated to 100 to 120 ° C. By cooling and precipitating with water, 12 parts of a dye of the probable ones are obtained. formula which draws from a sulfuric acid bath in brown tones on wool and polyamide fibers.
Beispie12 Aus 9 Teilen 3-Nitrophenylazomalondialdehyd und 10,5 Teilen
1-Hydroxy-2-aminobenzol-4-sulfonsäureanilid, gelöst in 200 Teilen Diglykol, werden
durch 8stündiges Erhitzen mit 15 Teilen Chrom(III)-chloridhexahydrat 21 Teile eines
Farbstoffs der wahrscheinlichen Formel
erhalten, der Wolle aus saurem Bad in braunroten Tönen färbt.
Entsprechende
Chromkomplexverbindungen stellt man aus folgenden Komponenten her:
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB51384A DE1106013B (en) | 1958-12-10 | 1958-12-10 | Process for the production of chromium complex dyes |
| DEB51424A DE1110348B (en) | 1958-12-10 | 1958-12-12 | Process for the production of chromium complex dyes |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB51384A DE1106013B (en) | 1958-12-10 | 1958-12-10 | Process for the production of chromium complex dyes |
| DEB51424A DE1110348B (en) | 1958-12-10 | 1958-12-12 | Process for the production of chromium complex dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1106013B true DE1106013B (en) | 1961-05-04 |
Family
ID=62597237
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB51384A Pending DE1106013B (en) | 1958-12-10 | 1958-12-10 | Process for the production of chromium complex dyes |
| DEB51424A Pending DE1110348B (en) | 1958-12-10 | 1958-12-12 | Process for the production of chromium complex dyes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB51424A Pending DE1110348B (en) | 1958-12-10 | 1958-12-12 | Process for the production of chromium complex dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (2) | DE1106013B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH599307A5 (en) * | 1974-05-09 | 1978-05-31 | Ciba Geigy Ag | |
| US4116952A (en) * | 1975-05-14 | 1978-09-26 | Ciba-Geigy Corporation | Unsymmetrical azo - azo methine 1:2 chromium complex dyes |
| DE2735286A1 (en) * | 1977-08-05 | 1979-02-22 | Basf Ag | METAL COMPLEX DYES |
-
1958
- 1958-12-10 DE DEB51384A patent/DE1106013B/en active Pending
- 1958-12-12 DE DEB51424A patent/DE1110348B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1110348B (en) | 1961-07-06 |
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