CH534251A - Dyeing natural and synthetic polyamides - navy blue shades - with azo and cpds chromium - Google Patents
Dyeing natural and synthetic polyamides - navy blue shades - with azo and cpds chromiumInfo
- Publication number
- CH534251A CH534251A CH822870A CH822870A CH534251A CH 534251 A CH534251 A CH 534251A CH 822870 A CH822870 A CH 822870A CH 822870 A CH822870 A CH 822870A CH 534251 A CH534251 A CH 534251A
- Authority
- CH
- Switzerland
- Prior art keywords
- chromium
- halogen
- synthetic polyamides
- cpds
- azo
- Prior art date
Links
- 239000004952 Polyamide Substances 0.000 title abstract description 13
- 229920002647 polyamide Polymers 0.000 title abstract description 13
- 238000004043 dyeing Methods 0.000 title description 9
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title description 5
- 229910052804 chromium Inorganic materials 0.000 title description 4
- 239000011651 chromium Substances 0.000 title description 4
- 238000000034 method Methods 0.000 claims description 11
- -1 monoazo compound Chemical class 0.000 claims description 11
- 239000004753 textile Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract description 11
- 150000002367 halogens Chemical class 0.000 abstract description 10
- 210000002268 wool Anatomy 0.000 abstract description 8
- 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 abstract description 5
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 229920002292 Nylon 6 Polymers 0.000 abstract description 2
- 229920002302 Nylon 6,6 Polymers 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 238000009736 wetting Methods 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 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 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 150000008049 diazo compounds Chemical class 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 238000004382 potting Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000001465 metallisation Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QLOKJRIVRGCVIM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]piperazine Chemical compound C1=CC(SC)=CC=C1CN1CCNCC1 QLOKJRIVRGCVIM-UHFFFAOYSA-N 0.000 description 1
- WASQBNCGNUTVNI-UHFFFAOYSA-N 2-amino-4,6-dichlorophenol Chemical compound NC1=CC(Cl)=CC(Cl)=C1O WASQBNCGNUTVNI-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 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
- 239000003086 colorant Substances 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000005406 washing Methods 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
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Natural and synthetic polyamides, e.g. wool, silk, nylon 6, nylon 6,6, are dyed navy-blue shades fast to light and wetting and esp. fast to alkaline perspiration, by treatment with a monazo cpd. of formula I (where R and R1 are each halogen; R2 is H or halogen; R3 is halogen or -OR4; R4 is opt. substd. alkyl) and with a cpd. yielding Cr, e.g. potassium bichromate, the monoazo cpd. and the agent yielding Cr being used in a mol. ratio of 2/1 - 2/2.
Description
Gegenstand der Erfindung ist ein Verfahren zum Färben von Fasern aus natürlichen und synthetischen Polyamiden mit Monoazoverbindungen, dadurch gekennzeichnet, dass man diese mit einer Monoazoverbindung der Formel
EMI1.1
wonn
R und R1 jeweils Halogen,
R2 Wasserstoff oder Halogen und
R3 Halogen oder -OR4 bedeuten und
R4 für einen gegebenenfalls substituierten Alkylrest steht, und mit einer chromabgebenden Verbindung behandelt.
Gute Färbungen erhält man, wenn man eine Monoazoverbindung der Formel
EMI1.2
worin R5 einen niedrigmolekularen Alkylrest bedeutet, verwendet.
Die Verbindungen der Formel (I) können erhalten werden, wenn man die Diazoverbindung aus einem Amin der Formel
EMI1.3
mit einer Kupplungskomponente der Formel
EMI2.1
kuppelt.
Die Kupplung kann in neutralem bis alkalischem wässrigem Medium, vorzugsweise bei einem pH-Wert von 8,0 bis 11,0, bei Temperaturen von -10 bis 60 , vorzugsweise von 0 bis 20 , gegebenenfalls in Gegenwart von Kupplungsbeschleunigern durchgeführt werden.
Halogen bedeutet zum Beispiel Brom, Fluor oder Jod, insbesondere jedoch ein Chloratom.
Alkylreste stehen hauptsächlich für niedrigmolekulare Alkylreste mit 1, 2, 3 oder 4 Kohlenstoffatomen.
Sind diese Reste substituiert, so enthalten sie meistens Halogenatome, Cyan-, Hydroxyl- oder Aminogruppen oder einen Arylrest, z. B. einen Phenylrest, Alkyl steht für solche Fälle für einen Aralkyl-, beispielsweise für einen Benzylrest.
Geeignete chromabgebende Verbindungen sind z. B.
Chromifluorid, Chromisulfat, Chromiformiat, Chromiacetat, Kaliumchromisulfat oder Ammoniumchromisulfat. Auch die Chromate, z. B. Natrium- oder Kaliumchromat bzw. -bichromat, eignen sich in vorzüglicher Weise für die Metallisierung der Monoazoverbindungen.
Natürliche Polyamide sind hauptsächlich Wolle und Seide, während die synthetischen Polyamide verschiedenster Zusammensetzung sein können, z. B. solche wie sie im SVF-Fachorgan 15, Seite 8 und 9 (1960) aufgeführt sind. Beispielsweise Polykondensationsprodukte aus w -Aminoundecylsäure oder e-Caprolactam oder Polykondensationsprodukte aus zweibasischen organischen Säuren, z. B. Adipin- oder Sebacinsäure mit Hexamethylendiamin, z. B. Nylon 6, Nylon 66, usw.
Das Färben kann nach bekannten Methoden durchgeführt werden. Beispielsweise kann man die Polyamide gleichzeitig im selben Färbebad mit einer Verbindung der Formel (I) und einem chromabgebenden Mittel behandeln, oder man kann die Polyamide zuerst mit einer Verbindung der Formel (I) behandeln und anschliessend die auf das Substrat aufgebrachte Verbindung mit einem chromabgebenden Mittel metallisieren, d. h. chromieren. Diese Nachmetallisierung kann im selben Färbebad oder in einem zweiten Färbebad durchgeführt werden.
Das Färben geschieht vorteilhaft in wässrig saurem Medium bei Temperaturen bis zu 100" C unter Zugabe von organischen Säuren, z. B. Essigsäure oder Ameisensäure und in Gegenwart z. B. von Natriumsulfat oder Ammoniumsulfat.
Die erhaltenen marineblauen Färbungen besitzen gute Licht- und Nassechtheiten, wie z. B. gute Wasch-, Meerwasser-, Schweiss-, Wasser-, Walk- und Pottingechtheit, ferner gute Carbonisier- und Reibechtheit.
Gegenüber den mit den nächstvergleichbaren bekannten und in Substanz metallisierten Farbstoffen aus der französischen Patentschrift Nr. 1 486 227, Beispiel 15, gefärbten Polyamiden besitzen die nach dem erfindungsgemässen Verfahren gefärbten Polyamide eine bessere Pottingechtheit.
Ferner ist überraschend, dass die nach dem erfindungsgemässen Verfahren gefärbten Polyamide bessere Echtheiten besitzen, z. B. bessere Pottingechtheit, als solche Färbungen, welche auf Polyamiden erhalten werden, wenn man diese mit in Substanz chromierten Monoazoverbindungen der Formel (I) färbt.
Ausserdem sind die Färbungen brillanter.
Aus der deutschen Patentschrift Nr. 220 392 ist ein Verfahren zur Herstellung von ortho-Oxymonoazofarbstoffen bekannt, welches darin besteht, dass man die Diazoverbindungen von Derivaten des o-Aminophenols, welche eine Nitrogruppe oder Halogen, oder beides, aber keine Sulfogruppe enthalten, mit 2-Arylamino-5 -naphthol-7 -sulfonsäure kuppelt. Mit den Farbstoffen kann man Wolle in saurem Bade färben und anschliessend nachchromieren.
Die Farbstoffe der Formel (I) besitzen, ebenfalls auf Wolle gefärbt und nachchromiert, wie eine bessere alkalische Schweissechtheit gegenüber den nächstvergleichbaren Farbstoffen aus der genannten deutschen Patentschrift.
In den folgenden Beispielen bedeuten die Teile Gewichtsteile, die Prozente Gewichtsprozente, die Temperaturen sind in Celsiusgraden angegeben.
Beispiel 1
1,5 Teile des Farbstoffs der Formel
EMI2.2
werden in 6000 Teilen Wasser bei 40 bis 50 gelöst und zu dieser Lösung 5 Teile Natriumsulfat, 2 Teile Eisessig und 2 Teile 85 %ige Ameisensäure gegeben. In diese Lösung trägt man nun 100 Teile Wollgabardine ein, worauf man das Färbebad innerhalb von 45 Minuten zum Kochen bringt und es während 30 Minuten bei dieser Temperatur kocht.
Nach dieser Zeit setzt man nochmals 2 Teile 85 %ige Ameisensäure zu und färbt erneut 30 Minuten lang bei Kochtemperatur. Nach dieser Zeit kühlt man das Färbebad auf 70" ab und versetzt dieses mit 0,75 Teilen Kaliumbichromat.
Hierauf wird das Färbebad wiederum auf Kochtemperatur gebracht und die Behandlung während 30 Minuten durchge führt. Die gefärbte Wollgabardine wird alsdann nach bekannten Methoden weiterbehandelt. Man erhält eine marineblaue Färbung mit guter Lichtechtheit und guten Nassechtheiten.
Beispiel 2
1,5 Teile des Farbstoffs aus Beispiel 1 werden zusammen mit 10 Teilen Natriumsulfat, 5 Teilen Ammoniumsulfat und 1,5 Teilen Kaliumbichromat in 6000 Teilen Wasser gelöst.
In diese Lösung trägt man nun bei 40O 100 Teile Wollgabardine ein, worauf man das Färbebad innerhalb 60 Minuten zum Kochen bringt und es während 90 Minuten bei dieser Temperatur hält. Nach dieser Zeit wird die gefärbte Wollgabardine nach bekannten Methoden weiterbehandelt. Man erhält eine gleichgute marineblaue Färbung wie in Beispiel 1.
Der Farbstoff in Beispiel 1 kann nach den Angaben der französischen Patentschrift Nr. 1 486 227 hergestellt werden, indem man die Diazoverbindung aus 1-Hydroxy-2-amino4,6-dichlorbenzol mit 2-(4' -Methoxyphenylamino)-5-hy- droxynaphthalin-7-sulfonsäure kuppelt.
Ähnlich gute Färbungen auf natürlichen und synthetischen Polyamiden erhält man, wenn man den folgenden Farbstoff nach den Verfahren der Beispiele 1 und 2 färbt:
EMI3.1
marinebl au PATENTANSPRUCH 1
Verfahren zum Färben von Textilfasern aus natürlichen und synthetischen Polyamiden mit Monoazoverbindungen, dadurch gekennzeichnet, dass man diese mit einer Monoazoverbindung der Formel
EMI3.2
worin R und R1 jeweils Halogen,
R2 Wasserstoff oder Halogen und
R3 Halogen oder -OR4 bedeuten und
R4 für einen gegebenenfalls substituierten Alkylrest steht, und mit einer chromabgebenden Verbindung behandelt.
The invention relates to a process for dyeing fibers made from natural and synthetic polyamides with monoazo compounds, characterized in that these are mixed with a monoazo compound of the formula
EMI1.1
wonn
R and R1 each halogen,
R2 hydrogen or halogen and
R3 is halogen or -OR4 and
R4 stands for an optionally substituted alkyl radical and is treated with a chromium-donating compound.
Good colorations are obtained when using a monoazo compound of the formula
EMI1.2
where R5 denotes a low molecular weight alkyl radical is used.
The compounds of the formula (I) can be obtained by converting the diazo compound from an amine of the formula
EMI1.3
with a coupling component of the formula
EMI2.1
clutch.
The coupling can be carried out in a neutral to alkaline aqueous medium, preferably at a pH of 8.0 to 11.0, at temperatures of -10 to 60, preferably from 0 to 20, optionally in the presence of coupling accelerators.
Halogen means, for example, bromine, fluorine or iodine, but especially a chlorine atom.
Alkyl radicals mainly stand for low molecular weight alkyl radicals with 1, 2, 3 or 4 carbon atoms.
If these radicals are substituted, they usually contain halogen atoms, cyano, hydroxyl or amino groups or an aryl radical, e.g. B. a phenyl radical, alkyl in such cases represents an aralkyl, for example a benzyl radical.
Suitable chromium-releasing compounds are, for. B.
Chromifluoride, Chromisulfat, Chromiformiat, Chromiacetat, Kaliumchromisulfat or Ammoniumchromisulfat. The chromates, e.g. B. sodium or potassium chromate or bichromate, are particularly suitable for the metallization of the monoazo compounds.
Natural polyamides are mainly wool and silk, while the synthetic polyamides can be of various compositions, e.g. B. those as listed in the SVF specialist organ 15, pages 8 and 9 (1960). For example, polycondensation products from w-aminoundecylic acid or e-caprolactam or polycondensation products from dibasic organic acids, e.g. B. adipic or sebacic acid with hexamethylenediamine, e.g. B. nylon 6, nylon 66, etc.
The dyeing can be carried out by known methods. For example, the polyamides can be treated simultaneously in the same dyebath with a compound of the formula (I) and a chromium donating agent, or the polyamides can first be treated with a compound of the formula (I) and then the compound applied to the substrate with a chromium donating agent metallize, d. H. chrome. This post-metallization can be carried out in the same dye bath or in a second dye bath.
The dyeing is advantageously carried out in an aqueous, acidic medium at temperatures of up to 100 ° C. with the addition of organic acids, for example acetic acid or formic acid, and in the presence of, for example, sodium sulfate or ammonium sulfate.
The navy blue dyeings obtained have good light and wet fastness properties, such as B. good fastness to washing, sea water, perspiration, water, fulling and potting, and also good fastness to carbonization and rubbing.
Compared to the polyamides dyed with the closest comparable known dyes metallized in substance from French Patent No. 1,486,227, Example 15, the polyamides dyed by the process according to the invention have better potting fastness.
It is also surprising that the polyamides dyed by the process according to the invention have better fastness properties, e.g. B. better potting fastness than those dyeings which are obtained on polyamides when they are dyed with monoazo compounds of the formula (I) chromated in substance.
In addition, the colors are more brilliant.
A process for the preparation of ortho-oxymonoazo dyes is known from German patent specification No. 220 392, which consists in that the diazo compounds of derivatives of o-aminophenol, which contain a nitro group or halogen, or both, but no sulfo group, with 2 -Arylamino-5-naphthol-7-sulfonic acid couples. The dyes can be used to dye wool in an acid bath and then re-chrome-plated.
The dyestuffs of the formula (I), also dyed on wool and chromed, have better alkaline perspiration fastness than the closest comparable dyestuffs from the above-mentioned German patent.
In the following examples, the parts are parts by weight, the percentages are percentages by weight and the temperatures are given in degrees Celsius.
example 1
1.5 parts of the dye of the formula
EMI2.2
are dissolved in 6000 parts of water at 40 to 50, and 5 parts of sodium sulfate, 2 parts of glacial acetic acid and 2 parts of 85% formic acid are added to this solution. 100 parts of wool gabardine are then introduced into this solution, whereupon the dyebath is brought to a boil within 45 minutes and it is boiled at this temperature for 30 minutes.
After this time, another 2 parts of 85% formic acid are added and dyeing is carried out again for 30 minutes at the boiling temperature. After this time, the dyebath is cooled to 70 "and 0.75 parts of potassium dichromate are added to it.
The dyebath is then brought to boiling temperature and the treatment is carried out for 30 minutes. The dyed wool gabardine is then treated further using known methods. A navy blue dyeing with good lightfastness and good wetfastnesses is obtained.
Example 2
1.5 parts of the dye from Example 1 are dissolved in 6000 parts of water together with 10 parts of sodium sulfate, 5 parts of ammonium sulfate and 1.5 parts of potassium dichromate.
100 parts of wool gabardine are then introduced into this solution at 40 °, whereupon the dyebath is brought to the boil within 60 minutes and it is held at this temperature for 90 minutes. After this time, the dyed wool gabardine is treated further using known methods. An equally good navy blue coloration as in Example 1 is obtained.
The dye in Example 1 can be prepared according to the information in French Patent No. 1 486 227 by converting the diazo compound from 1-hydroxy-2-amino4,6-dichlorobenzene with 2- (4'-methoxyphenylamino) -5-hy- droxynaphthalene-7-sulfonic acid couples.
Similar good colorations on natural and synthetic polyamides are obtained if the following dye is dyed according to the method of Examples 1 and 2:
EMI3.1
marinebl au PATENT CLAIM 1
Process for dyeing textile fibers made from natural and synthetic polyamides with monoazo compounds, characterized in that these are mixed with a monoazo compound of the formula
EMI3.2
wherein R and R1 are each halogen,
R2 hydrogen or halogen and
R3 is halogen or -OR4 and
R4 stands for an optionally substituted alkyl radical and is treated with a chromium-donating compound.
Claims (1)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH822870D CH822870A4 (en) | 1970-06-02 | 1970-06-02 | |
| CH822870A CH534251A (en) | 1970-06-02 | 1970-06-02 | Dyeing natural and synthetic polyamides - navy blue shades - with azo and cpds chromium |
| CA110,262A CA976544A (en) | 1970-06-02 | 1971-04-14 | Process for the dyeing of natural and synthetic polyamide fibres |
| CY879A CY879A (en) | 1970-06-02 | 1971-04-19 | Monoazo compounds,processes for their production and their use for the dyeing of natural and synthetic polyamide fibres |
| GB2733571*A GB1349551A (en) | 1970-06-02 | 1971-04-19 | Monoazo compounds processes for their production and their use for the dyeing of natural and synthetic polyamide fibres |
| US00144620A US3782897A (en) | 1970-06-02 | 1971-05-18 | Dyeing polyamide fibers with chromium-donating monoazo dyestuffs |
| DE2126814A DE2126814B2 (en) | 1970-06-02 | 1971-05-29 | 1: 1 and 1 ^ chromium complex azo dyes and processes for dyeing natural and synthetic polyamides |
| DE19712166609 DE2166609C3 (en) | 1970-06-02 | 1971-05-29 | Metal-free monoazo compounds and process for their preparation |
| BR3304/71A BR7103304D0 (en) | 1970-06-02 | 1971-05-31 | DYEING PROCESS OF SYNTHETIC NATURAL POLYAMIDES |
| ES391781A ES391781A1 (en) | 1970-06-02 | 1971-05-31 | PROCEDURE FOR OBTAINING MONOAZOIC DYES. |
| NL717107468A NL145300B (en) | 1970-06-02 | 1971-06-01 | PROCEDURE FOR DYEING FIBERS OF NATURAL AND SYNTHETIC POLYAMIDES WITH MONOAZO DYEES, AND TREATMENT WITH A CHROME-GIVING COMPOUND, THEREFORE DYED FIBERS AND PRODUCTS MADE FROM THEIR ARTICLES FOR THE SAME. |
| ZA713515A ZA713515B (en) | 1970-06-02 | 1971-06-01 | Process for the dyeing of natural and synthetic polyamide fibres |
| BE768012A BE768012A (en) | 1970-06-02 | 1971-06-02 | POLYAMIDE DYING PROCESS |
| FR7119959A FR2093985B1 (en) | 1970-06-02 | 1971-06-02 | |
| US05/378,257 US3948879A (en) | 1970-06-02 | 1973-07-11 | Phenylazonaphtholsulfonic acids having a substituted anilino group in the 6-position of the naphthalane ring |
| HK749/76*UA HK74976A (en) | 1970-06-02 | 1976-12-02 | Monoazo compounds, processes for their production, and their use for the dyeing of natural and synthetic polyamide fibres |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH822870A CH534251A (en) | 1970-06-02 | 1970-06-02 | Dyeing natural and synthetic polyamides - navy blue shades - with azo and cpds chromium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH534251A true CH534251A (en) | 1972-11-15 |
Family
ID=4337110
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH822870A CH534251A (en) | 1970-06-02 | 1970-06-02 | Dyeing natural and synthetic polyamides - navy blue shades - with azo and cpds chromium |
| CH822870D CH822870A4 (en) | 1970-06-02 | 1970-06-02 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH822870D CH822870A4 (en) | 1970-06-02 | 1970-06-02 |
Country Status (3)
| Country | Link |
|---|---|
| BR (1) | BR7103304D0 (en) |
| CH (2) | CH534251A (en) |
| ZA (1) | ZA713515B (en) |
-
1970
- 1970-06-02 CH CH822870A patent/CH534251A/en unknown
- 1970-06-02 CH CH822870D patent/CH822870A4/xx unknown
-
1971
- 1971-05-31 BR BR3304/71A patent/BR7103304D0/en unknown
- 1971-06-01 ZA ZA713515A patent/ZA713515B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR7103304D0 (en) | 1973-04-12 |
| CH822870A4 (en) | 1972-11-15 |
| ZA713515B (en) | 1973-01-31 |
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