DE1273729B - Process for the preparation of monoazo disperse dyes - Google Patents
Process for the preparation of monoazo disperse dyesInfo
- Publication number
- DE1273729B DE1273729B DES89424A DES0089424A DE1273729B DE 1273729 B DE1273729 B DE 1273729B DE S89424 A DES89424 A DE S89424A DE S0089424 A DES0089424 A DE S0089424A DE 1273729 B DE1273729 B DE 1273729B
- Authority
- DE
- Germany
- Prior art keywords
- molecular weight
- low molecular
- formula
- weight alkyl
- preparation
- 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
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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/081—Amino benzenes free of acid groups characterised by the amino group substituted amino group unsubstituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino, aralkylamino or arylamino
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/36—Material containing ester groups using dispersed dyestuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von Monoazo-Dispersionsfarbstoffen Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Dispersionsfarbstoffen der Formel worin A ein Wasserstoff-, Chlor- oder Bromatom, B einen durch Halogen, Cyan, Acyl oder Alkoxy substituierten Alkylrest mit 1 bis 3 Kohlenstoffatomen, D einen niedrigmolekularen Alkylrest, E einen niedrigmolekularen Alkylrest, G ein Wasserstoffatom oder einen gegebenenfalls substituierten niedrigmolekularen Alkyl- oder Alkoxyrest und X einen gegebenenfalls substituierten, niedrigmolekularen Alkylrest bedeutet, dadurch gekennzeichnet, daß man ein Amin der Formel _ diazotiert und mit einer Verbindung der Formel kuppelt. Als Substituenten an den Resten G und X kommen vor allem Chlor- oder Bromatome in Betracht. »Niedrigmolekulare« Reste enthalten 1 bis 4, vorzugsweise 1 bis 2 Kohlenstoffatome.Process for the preparation of monoazo disperse dyes The invention relates to a process for the preparation of disperse dyes of the formula wherein A is a hydrogen, chlorine or bromine atom, B is an alkyl radical having 1 to 3 carbon atoms substituted by halogen, cyano, acyl or alkoxy, D is a low molecular weight alkyl radical, E is a low molecular weight alkyl radical, G is a hydrogen atom or an optionally substituted low molecular weight alkyl or Alkoxy radical and X denotes an optionally substituted, low molecular weight alkyl radical, characterized in that an amine of the formula _ diazotized and with a compound of the formula clutch. Particularly suitable substituents on the radicals G and X are chlorine or bromine atoms. “Low molecular weight” radicals contain 1 to 4, preferably 1 to 2, carbon atoms.
Die erfindungsgemäß herstellbaren Farbstoffe ergeben violette bis blaue Färbungen.The dyes that can be prepared according to the invention give violet to blue colorations.
Im allgemeinen findet die Kupplung in saurem, gegebenenfalls gepuffertem Medium unter Kühlen, beispielsweise bei 0 bis 5'C, statt. Als Puffersubstanz kommt insbesondere Natriumacetat in Betracht. Die Verarbeitung der Farbstoffe der Formel (I) zu Färbepräparaten erfolgt auf allgemein bekannte Weise, z. B. durch Mahlen in Gegenwart von Dispergierund,;'oder Füllmitteln. Mit den gegebenenfalls im Vakuum oder durch Zerstäuben getrockneten Pr<ipa-. raten kann man, nach Zugabe von mehr oder °a@eniger Wasser in sogenannter langer oder kurzer Flotte färben, klotzen oder bedrucken. Die Farbstoffe ziehen aus wäßriger Suspension. ausgezeichnet auf Textilmaterial aus vollsynthetischen oder halbsynthetischen, hydrophoben, hochmolekularen organischen Stoffen auf. Besonders geeignet sind sie zum Färben oder Bedrucken von Textilmaterial aus linearen, aromatischen Polyestern sowie aus Cellulose-21/2 Acetat, Cellulosetriacetat und synthetischen Polyamiden.In general, the coupling takes place in acidic, optionally buffered Medium with cooling, for example at 0 to 5'C, instead. Comes as a buffer substance especially sodium acetate. Processing the dyes of the formula (I) to dye preparations is carried out in a generally known manner, e.g. B. by grinding in the presence of dispersants, ';' or fillers. With the possibly in a vacuum or spray-dried Pr <ipa-. you can guess after adding more or ° a @ some water in so-called long or short liquor color, pad or to print. The dyes are drawn from an aqueous suspension. excellent on textile material from fully synthetic or semi-synthetic, hydrophobic, high molecular organic Fabrics on. They are particularly suitable for dyeing or printing textile material from linear, aromatic polyesters as well as from cellulose-21/2 acetate, cellulose triacetate and synthetic polyamides.
Gefärbt, geklotzt oder bedruckt wird nach allgemein bekannten Methoden.Generally known methods are used to dye, pad or print.
Die erhaltenen Färbungen sind außerordentlich echt, z. B. hervorragend thermofixier-, sublimier-, plissier-, rauchgas-, überfärbe-, trockenreinigungs-, chlor- und naßecht, z. B. wasser-, wasch- und schweißecht. Ätzbarkeit und Reserve von Wolle und Baumwolle sind gut. Hervorragend ist die Lichtechtheit, selbst in hellen Tönen, so daß die neuen Farbstoffe auch als Mischungskomponenten für die 1-lerstellung pastellfarbener Modetöne sehr geeignet sind. Die Farbstoffe sind bei Temperaturen bis zu mindestens 220° C und besonders bei 80 bis 140'C verkoch-und reduktionsbeständig.The dyeings obtained are extremely fast, e.g. B. excellent thermosetting, subliming, pleating, smoke gas, dyeing, dry cleaning, chlorine and wet fast, z. B. water, wash and sweat resistant. Etchability and reserve of wool and cotton are good. The lightfastness is excellent, even in light tones, so that the new dyes can also be used as mixing components for the 1 creation of pastel-colored fashion tones are very suitable. The dyes are at Temperatures up to at least 220 ° C and especially at 80 to 140'C overcooking and resistant to reduction.
Diese Beständigkeit wird weder durch das Flottenverhältnis noch durch die Gegenwart von Färbebeschleunigern ungünstig beeinflußt. In den bekanntgemachten Unterlagen des belgischen Patents b14027 sind strukturell ähnliche Farbstoffe beschrieben. Die erfindungsgemäß herstellbaren Farbstoffe besitzen gegenüber dem nächstvergleichbaren Farbstoff aus den genannten belgischen Patentunterlagen ein besseres Ziehvermögen.This resistance is neither by the liquor ratio nor by the presence of dye accelerators adversely affected. In the advertised Structural similar dyes are described under Belgian patent b14027. Possess the dyes which can be prepared according to the invention opposite to the closest comparable dye from the aforementioned Belgian patent documents a better drawability.
Die iin folgenden Beispiel genannten Teile sind Gewichtsteile, die Temperaturen sind in Celsiusgraden angegeben. Beispiel 1 Zu 120 Teilen konzentrierter Schwefelsäure werden bei 60 bis 70° langsam unter kräftigem Rühren 6,9 Teile gepulvertes Natriumnitrit gegeben. Man rührt weitere 10 Minuten bei 60°, kühlt dann auf 10° ab und fügt bei 15 bis 25° 100 Teile Eisessig und danach 25 Teile 1 Amino-2-methylsulfonyl-4-nitrobenzol und 100 Teile Eisessig zu. Man rührt 2 Stunden bei 10° und versetzt mit 8 Teilen Harnstoff. Nach 10 Minuten gießt man die Diazoniumsalzlösung zu einem Gemisch aus 29,8 Teilen 3-N,N-Diäthylamino-4-äthoxy-l-(chlorpropionyl)-aminobenzol, 50 Teilen Eisessig und 200 Teilen Eis. Die Kupplung wird in saurem Medium bei 0° zu Ende geführt. Der erhaltene Farbstoff wird abfiltriert, säurefrei gewaschen und getrocknet. Er färbt synthetische Fasern in blauen Tönen mit sehr guten Echtheiten. Färbevorschrift 7 Teile des nach Beispiel 1 erhaltenen Farbstoffs werden mit 4 Teilen dinaphthylmethandisulfonsaurem Natrium, 4 Teilen Natriumacetylsulfat und 5 Teilen wasserfreiem Natriumsulfat in einer Kugelmühle 48 Stunden zu einem feinen Pulver gemahlen. Mit dem so erhaltenen Färbepräparat kann ein Polyesterfasergewebe, z. B. unter Zusatz von Laurylsulfonat und der Emulsion eines chlorierten Benzols in Wasser, bei 80 bis 100° oder in Abwesenheit eines Färbebeschleunigers unter Druck bei 110 bis 140° gefärbt werden.The parts mentioned in the following example are parts by weight which Temperatures are given in degrees Celsius. Example 1 More concentrated to 120 parts Sulfuric acid is slowly powdered at 60 to 70 ° with vigorous stirring 6.9 parts Given sodium nitrite. The mixture is stirred for a further 10 minutes at 60 °, then cooled to 10 ° and adds 100 parts of glacial acetic acid at 15 ° to 25 ° and then 25 parts of 1-amino-2-methylsulfonyl-4-nitrobenzene and 100 parts of glacial acetic acid. The mixture is stirred for 2 hours at 10 ° and 8 parts are added Urea. After 10 minutes, the diazonium salt solution is poured into a mixture 29.8 parts of 3-N, N-diethylamino-4-ethoxy-1- (chloropropionyl) aminobenzene, 50 parts Glacial acetic acid and 200 parts of ice. The coupling is completed in an acidic medium at 0 °. The dye obtained is filtered off, washed free of acid and dried. He dyes synthetic fibers in blue tones with very good fastness properties. Dyeing prescription 7 parts of the dye obtained according to Example 1 are mixed with 4 parts of dinaphthylmethandisulfonsaurem Sodium, 4 parts of sodium acetyl sulfate and 5 parts of anhydrous sodium sulfate in ground to a fine powder in a ball mill for 48 hours. With the so obtained Dye preparation can be a polyester fiber fabric, e.g. B. with the addition of lauryl sulfonate and the emulsion of a chlorinated benzene in water, at 80 to 100 ° or in the absence a dyeing accelerator can be dyed under pressure at 110 to 140 °.
Die in der folgenden Tabelle angegebenen Farbstoffe werden in der
in dem zuvor genannten Beispiel beschriebenen Weise hergestellt.
Claims (1)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH194563A CH422194A (en) | 1963-02-15 | 1963-02-15 | Process for the production of azo dyes that are sparingly soluble in water |
CH358169A CH474559A (en) | 1963-02-15 | 1963-02-15 | Process for the production of azo dyes that are sparingly soluble in water |
CH682163A CH468444A (en) | 1963-02-15 | 1963-05-31 | Process for the production of azo dyes that are sparingly soluble in water |
CH682263A CH476803A (en) | 1963-02-15 | 1963-05-31 | Process for the production of azo dyes that are sparingly soluble in water |
CH813363 | 1963-07-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1273729B true DE1273729B (en) | 1968-07-25 |
Family
ID=27509023
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DES89424A Pending DE1273729B (en) | 1963-02-15 | 1964-02-07 | Process for the preparation of monoazo disperse dyes |
Country Status (2)
Country | Link |
---|---|
BE (1) | BE643775A (en) |
DE (1) | DE1273729B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2022290A1 (en) * | 1968-10-18 | 1970-07-31 | Sandoz Sa | |
WO2015193481A3 (en) * | 2014-06-20 | 2016-03-17 | Amazon Technologies, Inc. | Dye compound, fluid carrier and electrowetting apparatus |
CN114773874A (en) * | 2022-04-10 | 2022-07-22 | 浙江博澳新材料股份有限公司 | Purple lightfast alkali-washable disperse dye and preparation method thereof |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1290915B (en) * | 1966-02-17 | 1969-03-20 | Bayer Ag | Process for dyeing and printing fiber materials made from aromatic polyesters and cellulose acetates |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE748473C (en) * | 1936-11-19 | 1944-11-03 | Process for the preparation of water-insoluble monoazo dyes | |
BE614027A (en) * | 1961-02-16 | 1962-08-16 | Hoechst Ag | Water insoluble monoazo dyes and their preparation |
-
1964
- 1964-02-07 DE DES89424A patent/DE1273729B/en active Pending
- 1964-02-13 BE BE643775D patent/BE643775A/xx unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE748473C (en) * | 1936-11-19 | 1944-11-03 | Process for the preparation of water-insoluble monoazo dyes | |
BE614027A (en) * | 1961-02-16 | 1962-08-16 | Hoechst Ag | Water insoluble monoazo dyes and their preparation |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2022290A1 (en) * | 1968-10-18 | 1970-07-31 | Sandoz Sa | |
WO2015193481A3 (en) * | 2014-06-20 | 2016-03-17 | Amazon Technologies, Inc. | Dye compound, fluid carrier and electrowetting apparatus |
CN106471003A (en) * | 2014-06-20 | 2017-03-01 | 亚马逊科技公司 | Dye composition, fluid carrier and electrowetting device |
US10338372B2 (en) | 2014-06-20 | 2019-07-02 | Amazon Technologies, Inc. | Carrier fluid compounds and dye compounds for electrowetting apparatus |
CN114773874A (en) * | 2022-04-10 | 2022-07-22 | 浙江博澳新材料股份有限公司 | Purple lightfast alkali-washable disperse dye and preparation method thereof |
CN114773874B (en) * | 2022-04-10 | 2023-08-01 | 浙江博澳新材料股份有限公司 | Purple sun-proof alkali-washable disperse dye and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
BE643775A (en) | 1964-05-29 |
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