DE3200969A1 - Azo dye modification - Google Patents

Azo dye modification

Info

Publication number
DE3200969A1
DE3200969A1 DE19823200969 DE3200969A DE3200969A1 DE 3200969 A1 DE3200969 A1 DE 3200969A1 DE 19823200969 DE19823200969 DE 19823200969 DE 3200969 A DE3200969 A DE 3200969A DE 3200969 A1 DE3200969 A1 DE 3200969A1
Authority
DE
Germany
Prior art keywords
modification
dye
azo dye
formula
dye modification
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.)
Withdrawn
Application number
DE19823200969
Other languages
German (de)
Inventor
Horst Dr. 5068 Odenthal Brandt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Priority to DE19823200969 priority Critical patent/DE3200969A1/en
Publication of DE3200969A1 publication Critical patent/DE3200969A1/en
Withdrawn legal-status Critical Current

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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0025—Crystal modifications; Special X-ray patterns
    • C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
    • C09B67/0029—Crystal modifications; Special X-ray patterns of azo compounds of monoazo compounds
    • 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
    • C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
    • C09B29/0847—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 substituted by halogen

Abstract

The novel crystallographic modification of the dye of the formula <IMAGE> of interplanar spacings d/ ANGSTROM of 11.27, 9.74, 7.28, 6.64, 5.99 and 4.08 and relative intensities 90, 100, 90, 30, 50 and 60 is distinguished by very good dye bath stability. It is obtained by heat-treating the unstable alpha -modification.

Description

AzofarbstoffmodifikationAzo dye modification

Gegenstand der Erfindung ist eine neue kristallographische Modifikation (P-Modifikation) des Farbstoffs der Formel Die neue Modifikation ist gekennzeichnet durch die Netzebenenabstände d/2 11.27, 9.74, 7.28, 6.64, 5.99 und 4.08 mit den relativen Intensitäten 90, 100, 90, 30, 50 und 60.The invention relates to a new crystallographic modification (P modification) of the dye of the formula The new modification is characterized by the lattice plane spacings d / 2 11.27, 9.74, 7.28, 6.64, 5.99 and 4.08 with the relative intensities 90, 100, 90, 30, 50 and 60.

Die angegebenen Netzebenenabstände werden aus den sechs stärksten Linien in dem als Fig. 1 beigefügten DEBYE-SCHERRER-Diagramm (Wellenlänge 1.54 i der Cu-K-oc-strahlung) errechnet.The specified lattice plane spacings are derived from the six strongest Lines in the DEBYE-SCHERRER diagram attached as Fig. 1 (wavelength 1.54 i the Cu-K-oc radiation).

Die Farbstoffe der Formel I - als solche - sind an sich bekannt (vgl. EP-OS 0 027 887). Man erhält diese Farbstoffe nach dort gemachten Angaben in üblicher Weise durch Diazotieren und Kuppeln, wobei jedoch eine andere kristalline Form (M-Modifikation) anfällt, die durch die Netzebenenabstände d/A 7.94, 7.23, 5.17, 4.62, 3.81, 3.68, 3.63 und 3.25 mit den Intensitäten 40, 35, 50, 35, 100, 35, 35 und 60 (vgl. Fig. 2) und eine unzureichende Färbebadstabilität - im Gegensatz zu der erfindungsgemäßen ß-Modifikation - gekennzeichnet sind.The dyes of the formula I - as such - are known per se (cf. EP-OS 0 027 887). These dyes are obtained in a conventional manner according to the information given there Way by diazotization and coupling, but with a different crystalline form (M-modification) incurred by the Grid level spacings d / A 7.94, 7.23, 5.17, 4.62, 3.81, 3.68, 3.63 and 3.25 with the intensities 40, 35, 50, 35, 100, 35, 35 and 60 (see. Fig. 2) and insufficient dye bath stability - in contrast to the ß-modification according to the invention - are marked.

Die Umwandlung der s-Modifikation erfolgt beispielsweise durch Erhitzen der wäßrigen Farbstoffdispersion in Gegenwart von üblichen Dispergiermitteln im Temperaturbereich von 80-1200C oder durch Vermahlen in Rührwerksmühlen bei 80-95°C.The s-modification is converted, for example, by heating the aqueous dye dispersion in the presence of conventional dispersants in the Temperature range from 80-1200C or by grinding in agitator mills at 80-95 ° C.

Die erfindungsgemäße ß-Modifikation wird durch Erhitzen des bei der Synthese anfallenden wäßrigen Nutschkuchens in Gegenwart von Dispergiermitteln im Temperaturbereich zwischen 80° und 1200C oder durch Vermahlen in Rührwerksmühlen bei 80" bis 950C erzeugt.The ß-modification according to the invention is by heating the at the Synthesis of resulting aqueous filter cake in the presence of dispersants in the Temperature range between 80 ° and 1200C or by grinding in agitator mills generated at 80 "to 950C.

Beispiel 230 g des wäßrigen Preßkuchens des Farbstoffs der Formel (I) in der i-Modifikation mit etwa 30 % Rohfarbstoffgehalt werden mit 500 cm3 Wasser und 2 % eines handelsüblichen nichtionogenen Emulgators (bezogen auf Rohfarbstoff) angeschlagen, homogenisiert und etwa 1 Stunde bei 980C getempert. Der Farbstoff hat sich vollständig in die -Modifikation umgewandelt. Danach wird diese isoliert und mit 200 % (bezogen auf Rohfarbstoff) eines Ligninsulfonats versetzt und in einer Perlmühle bei 85-800C 15 Minuten gemahlen, anschließend wird bei Raumtemperatur nochmals 45 bis 60 Minuten gemahlen. Die erhaltene Suspension wird im Sprühtrockner getrocknet.Example 230 g of the aqueous press cake of the dye of the formula (I) in the i-modification with about 30% raw dye content are mixed with 500 cm3 of water and 2% of a commercially available non-ionic emulsifier (based on raw dye) beaten, homogenized and tempered for about 1 hour at 980C. The dye has completely transformed into the modification. Then this is isolated and mixed with 200% (based on raw dye) of a lignosulfonate and in one Bead mill is ground at 85-800C for 15 minutes, then at room temperature ground again for 45 to 60 minutes. The suspension obtained is in the spray dryer dried.

Die so hergestellte Farbstoffpräparation mit einem Gehalt von 31 Ps Farbstoff ergibt auf Polyester-Wickelkörpern, sowohl unter HT-Bedingungen als auch nach dem Carrier-Verfahren egale Färbungen.The dye preparation produced in this way with a content of 31 Ps Dye yields on polyester cores, both under HT conditions and level dyeings using the carrier process.

Claims (3)

Patentansprüche: 1. Kristallographische Modifikation des Azofarbstoffs der Formel gekennzeichnet durch die Netzebenenabstände d/2 11.27, 9.74, 7.28, 6.64, 5.99 und 4.08 mit den relativen Intensitäten 90, 100, 90, 30, 50 und 60.Claims: 1. Crystallographic modification of the azo dye of the formula characterized by the lattice plane spacings d / 2 11.27, 9.74, 7.28, 6.64, 5.99 and 4.08 with the relative intensities 90, 100, 90, 30, 50 and 60. 2. Verfahren zum Färben von Polyesterfasern, dadurch gekennzeichnet, daß man die kristallographische Modifikation des Farbstoffs gemäß Anspruch 1 einsetzt.2. A method for dyeing polyester fibers, characterized in that that the crystallographic modification of the dye according to claim 1 is used. 3. Farbstoffpräparation enthaltend die Modifikation gemäß Anspruch 1.3. Dyestuff preparation containing the modification according to claim 1.
DE19823200969 1982-01-14 1982-01-14 Azo dye modification Withdrawn DE3200969A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19823200969 DE3200969A1 (en) 1982-01-14 1982-01-14 Azo dye modification

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19823200969 DE3200969A1 (en) 1982-01-14 1982-01-14 Azo dye modification

Publications (1)

Publication Number Publication Date
DE3200969A1 true DE3200969A1 (en) 1983-07-21

Family

ID=6153066

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19823200969 Withdrawn DE3200969A1 (en) 1982-01-14 1982-01-14 Azo dye modification

Country Status (1)

Country Link
DE (1) DE3200969A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0234474A2 (en) * 1986-02-27 1987-09-02 Bayer Ag Gamma modification of a benzisothiazole dye

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0234474A2 (en) * 1986-02-27 1987-09-02 Bayer Ag Gamma modification of a benzisothiazole dye
EP0234474A3 (en) * 1986-02-27 1990-10-31 Bayer Ag Gamma modification of a benzisothiazole dye

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