CH224647A - Process for chromating a stain dye. - Google Patents
Process for chromating a stain dye.Info
- Publication number
- CH224647A CH224647A CH224647DA CH224647A CH 224647 A CH224647 A CH 224647A CH 224647D A CH224647D A CH 224647DA CH 224647 A CH224647 A CH 224647A
- Authority
- CH
- Switzerland
- Prior art keywords
- chromating
- chromium
- acid
- dye
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000004532 chromating Methods 0.000 title claims description 6
- 239000000975 dye Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- 239000011651 chromium Substances 0.000 claims description 5
- 239000000983 mordant dye Substances 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 13
- 150000001845 chromium compounds Chemical class 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000001844 chromium Chemical class 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical class 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 2
- 238000005254 chromizing Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- HEUMNKZPHGRBKR-UHFFFAOYSA-N [Na].[Cr] Chemical compound [Na].[Cr] HEUMNKZPHGRBKR-UHFFFAOYSA-N 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- -1 diamine compounds Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000006467 substitution reaction 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
- C09B45/01—Complex metal compounds of azo dyes characterised by the method of metallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Chromierung eines Beizenfarbstoffes. Im Schrifttum sind viele Verfahren zur Ohromierung von sulfons5,uregruppenhalti- gen Beizenfarbs-tefien bekannt geworden, die alle entweder in der Anwendung von Chromisalzen,oder von Chromhydroxyd bezw. Chromiten bestehen.
Nach all diesen bekannten Verfahren gehen sulfonsäur-egruppenfreie -o-Oxycarboxy- farbstoffe vom Typus des Eriochromazurols B(Schultz-Lehmann, Farbstofftabellen, <B>7.</B> Auf lage, Nr. <B>838)</B> oder des Eri-oellromflavin3 <B>A</B> (lo,c. eit. Nr. <B>258)</B> in vollständig unlösliche Verbindungen über.
Es ist ferner 'bekannt, dass sulfonsäure- gruppenfreie o,o-Dioxyazofarbstoff-o durch Behandlung mit Chromisalzen in wässrig- alko,holischer Lösung oder durch Einwirkung chromabgebender Mittel in alkalischem Me dium in Gegenwart von Salzen aliphatischer o-Oxycarbonsäuren inalkohollösliclie Chrom- verbind:ungen übergeführt werden können, die aber nicht waeserlöslich, sind.
Es wurde nun die überrasAende Ent deckung gemacht, dass s-alfensäuregruppen- freie Beizenfarbstoffe der oben genannten<B>Ty-</B> pen in waseterlösliche Chromverbindungen übergeführt werden können, wenn man sie in wässriger Lösung oder Suspension bei erhöll- ter Temperatur offen oder unter Druck mit komplexen Chromverbindungen von aromati schen o-Oxycarbioneäuren behandelt und da,
- bei auf<B>jede</B> eliro-mierbare Gruppe ödes Beizen- farbstoffes mindestens ein Atom Chrom an wendet.
Komplexe Cliromverbind:ungen von aro- matisv,hen o,-Oxy#earbo-nsäuren erhält man nach Barbieri (R.<B>A.</B> L.<B>[5]</B> 24 1.<B>608)</B> durch Behandlung ihrer Alkalisalzlösungen mit Chromisalzen. Geeignete o-Oxy- earbons,äuren sind beispielsweise die Salicyl- säure, ihre Homologen und Substitutionspro- dukte, wie Sulfosalicy1säure,
Sullokresotin- Auren, ferner o-Oxynaplitoos#äuren und ihre Substitutienspro,dukte, wie Sullo-ss-o#xynaph- toesäure usw. Auch, Diaminverbindungen komplex-er Cliromverbindungen aromatischer o-Oxycarbon,sä,ur,en, wie Diamin-ehro#msalieyl- säure bezw. ihre Alkaliealze,
die man bei- spielsweise aus ehromsalicyl!sauren Alkali- salzen beim Stehen mit überschüssigen Ami- n-en wie Ammoniak, Alkylaminen, Äthylen- diamin, Pyridin, als rotviolette kristallisierte Verbindungen erhält, sind zur Verwendung nach vorliegendem Verfahren geeignet.
Die Bildung wasserlöslicher Chromver- bin,dungen von sulfonsäuregruppenfreienBei- zenfarbstoffen war nicht vorauszusehen, und der sehr glatte Verlauf der Chromierun,g ist überraschend, besonders da komplexe Chrom verbindungen von aliphatischen o-Oxycarbon- säuren, wie Versuche zeigten, als chromab gebende Mittel' für die Chromierung von Beizenfarbstoffen nicht sehr zweckdienlich sind.
Die neuen wasserlöslichen Chromverbin dungen von sulfonsäuregruppenfreien o-Oxy- carboxyfarbstoffen erweitern das Anwen dungsgebiet vieler längst bekannter Farb stoffe. Sie können beispielsweise zum Färben von Cellulose wie Baumwolle oder Papier, zum Färben von Seide aus schwach saurem Bad oder von Leder Verwendung finden.
Gegenüber den nach bekannten Chromie- rungs#verfahren erhältlichen analogen, voll ständig wasserunlösliehen Chromverbindun- genstellen die neuen wasserlö#slichen Chrom verbindungen eine wesentliche Bereicherung ,der Technik dar.
Die neuen wasserlöslichen Chromverbin dungen von sulfonsäuregruppenfreien o,o'-Di- oxyazofarbstoffen ziehen aus schwach saurem Bad gleichmässig auf tierische Fasern und teilweise auch auf Baumwolle. Sie eignen ,sich auch zum Färben von Leder.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Chromierung des durch Kuppeln von dia-zotiertem 4-Nitro-2-amino- phenol mit 1-Phenyl-3-methyl-5-pyrazolon erhaltenen Beizenfarbstoffes, dadurch ge kennzeichnet, dass man<B>1</B> Mol dieses Farb stoffes in wässriger Lösung bei erhöhter Tem peratur mit mindestens<B>1</B> Mol Sulfesalieyl- säure-Chromkomplexverbindung behandelt.
Be40et: <B>19,6</B> Teile des sulfonsäuregruppenfreien Fa#rbstoffes, erhalten auodiazotiertera4-Nitru- 2-aminophenol und 1-Phenyl-'3-methyl-5-pyr- azolon, werden in<B>800</B> Teilen heissem Wasser mit<B>100</B> Teilen 34%iger Natronlauge gelöst und mit<B>130</B> Teilen einer Lösung von chrom- ,sulfosalicylsaurem Natrium (entsprechend <B>5</B> Teilen Chromoxyd) unter Rückfluss ge kocht.
Die orangegefärbte Lösung scheidet dabei etwa<B>5</B> Teile brauner Kriställchen aus, die nach 2 Stunden heiss abfiltriert werden. Die neue wasserlösliche Chromverbindung gewinnt aus dem Filtrat durch Aus-salzen. Sie erzeugt aus schwachsaurem Bad auf tie- rWher Faser gut lichtechte, gleichmässige, gelborange Färbungen.
Gleiche Produkte erhält man mit ehrom- sulfo,s#alicylsaurem Ammonium und diamin- ehremsulfosalieyl#saurem Ammonium.
Man erhält die genannten Chromierungs- mittel duixh Auflösung von<B>1</B> Grammatem Chromhydroxyd in, ein-er Lösung von 2 Gramm atomen Sulfosalicylsäure in<B>1</B> Liter Waffle!r und Neutralisation mit Soda bezw. Ammo niak bis zu bleibender lackmusneutraler Re aktion.
Das diaminehr mulfoselicylsaure Ammonium erhält man aus ehromsulfosali- cy1saurem, Ammonium als pfirsichblütenrote Kriställchen beim Stehen der mit NH, ge sättigten Lösung. Mit Aminen, wieAthylen- diamin, Alkylaminen, Pyridin, Piperidin usw., erhält man analoge Verbindungen.
Process for chromating a stain dye. In the literature, many processes for the odorization of sulfonic acid, acidic stains containing urine groups, have become known, all of which either involve the use of chromium salts or of chromium hydroxide and / or. Chromites exist.
All these known processes are based on sulfonic acid-o-oxycarboxy dyes of the eriochromazurols B type (Schultz-Lehmann, Dye Tables, 7th edition, no. 838) or of the Eri-oellromflavin3 <B> A </B> (lo, c. eit. no. <B> 258) </B> into completely insoluble compounds.
It is also known that sulfonic acid group-free o, o-dioxyazo dye-o by treatment with chromium salts in aqueous alcohol, holic solution or by the action of chromium-releasing agents in alkaline medium in the presence of salts of aliphatic o-oxycarboxylic acids in alcohol-soluble chromium compounds: ungen can be transferred, but which are not soluble in water.
The surprising discovery has now been made that stain dyes of the abovementioned types, free of s-alfenic acid groups, can be converted into water-soluble chromium compounds if they are left open in aqueous solution or suspension at elevated temperature or treated under pressure with complex chromium compounds of aromatic o-oxycarbionic acids and there,
- at least one atom of chromium applies to <B> each </B> elutable group of dull mordant dye.
Complex cliromal compounds of aromatic, hen, o, -oxy, earbo-n acids are obtained according to Barbieri (R. <B> A. </B> L. <B> [5] </B> 24 1. < B> 608) </B> by treating your alkali salt solutions with chromium salts. Suitable o-oxy-carboxylic acids are, for example, salicylic acid, its homologues and substitution products, such as sulfosalicic acid,
Sullocresotinic auras, also o-oxynaplitous acids and their substitute products, such as sullo-ss-oxynaphthoic acid, etc. Also, diamine compounds, complex cliromic compounds of aromatic o-oxycarbon, acids, urines, such as diamine-ehro # msalieyl acid or their alkali salts,
those obtained, for example, from eromalicylic acid alkali salts on standing with excess amines such as ammonia, alkylamines, ethylene diamine, pyridine, as red-violet crystallized compounds, are suitable for use in the present process.
The formation of water-soluble chromium compounds of sulphonic acid group-free behen dyes could not be foreseen, and the very smooth course of the chromizing is surprising, especially since complex chromium compounds of aliphatic o-oxycarboxylic acids, as experiments have shown, are used are not very useful for the chromating of mordant dyes.
The new water-soluble chromium compounds of sulphonic acid group-free o-oxycarboxy dyes expand the field of application of many long-known dyes. They can be used, for example, for dyeing cellulose such as cotton or paper, for dyeing silk from a weakly acidic bath, or leather.
Compared to the analogous, completely water-insoluble chromium compounds obtainable by known chromizing processes, the new water-soluble chromium compounds represent a significant enrichment in technology.
The new water-soluble chromium compounds of sulfonic acid group-free o, o'-dioxyazo dyes move evenly from a weakly acidic bath onto animal fibers and sometimes also onto cotton. They are also suitable for dyeing leather.
The subject of the present patent is a process for chromating the mordant dye obtained by coupling diazotized 4-nitro-2-aminophenol with 1-phenyl-3-methyl-5-pyrazolone, characterized in that <B> 1 </B> Mol of this dye in aqueous solution at elevated temperature treated with at least <B> 1 </B> mol of sulphesalylic acid-chromium complex compound.
Be40et: 19.6 parts of the sulfonic acid group-free dye, obtained auodiazotized α4-nitru-2-aminophenol and 1-phenyl-3-methyl-5-pyrazolone, are obtained in 800 / B> Parts of hot water with <B> 100 </B> parts of 34% sodium hydroxide solution and <B> 130 </B> parts of a solution of sodium chromium, sulfosalicylic acid (corresponding to <B> 5 </B> Parts of chromium oxide) boiled under reflux.
The orange-colored solution separates about <B> 5 </B> parts of brown crystals, which are filtered off while hot after 2 hours. The new water-soluble chromium compound is obtained from the filtrate by salting out. From a weakly acidic bath on deeper fibers, it produces good, lightfast, even, yellow-orange colorations.
The same products are obtained with Ehrom-sulfo, s # alicylic acid ammonium and diamine-Ehremsulfosalieyl® acid ammonium.
The chromating agents mentioned are obtained by dissolving 1 gram of chromium hydroxide in a solution of 2 grams of atoms of sulfosalicylic acid in 1 liter of wafer and neutralizing with soda or water. Ammonia up to permanent litmus-neutral reaction.
The diaminehrmulfoselicylic acid ammonium is obtained from Ehromsulfosalicy1saurem ammonium as peach-blossom-red crystals when the solution is saturated with NH3. With amines, such as ethylene diamine, alkylamines, pyridine, piperidine, etc., analogous compounds are obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH224647T | 1941-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH224647A true CH224647A (en) | 1942-12-15 |
Family
ID=4453648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224647D CH224647A (en) | 1941-10-15 | 1941-10-15 | Process for chromating a stain dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH224647A (en) |
-
1941
- 1941-10-15 CH CH224647D patent/CH224647A/en unknown
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