DE2120877B2 - Monoazo compounds sparingly soluble in water, process for their preparation and their use - Google Patents

Monoazo compounds sparingly soluble in water, process for their preparation and their use

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Publication number
DE2120877B2
DE2120877B2 DE19712120877 DE2120877A DE2120877B2 DE 2120877 B2 DE2120877 B2 DE 2120877B2 DE 19712120877 DE19712120877 DE 19712120877 DE 2120877 A DE2120877 A DE 2120877A DE 2120877 B2 DE2120877 B2 DE 2120877B2
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Germany
Prior art keywords
cjh
coo
pink
water
parts
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.)
Granted
Application number
DE19712120877
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German (de)
Other versions
DE2120877C3 (en
DE2120877A1 (en
Inventor
Wolfgang Dr. Oberwil Groebke (Schweiz)
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.)
Sandoz Patent GmbH
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Sandoz Patent GmbH
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Filing date
Publication date
Priority claimed from CH680870A external-priority patent/CH526615A/en
Application filed by Sandoz Patent GmbH filed Critical Sandoz Patent GmbH
Publication of DE2120877A1 publication Critical patent/DE2120877A1/en
Publication of DE2120877B2 publication Critical patent/DE2120877B2/en
Application granted granted Critical
Publication of DE2120877C3 publication Critical patent/DE2120877C3/en
Expired legal-status Critical Current

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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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
    • C09B43/20—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Description

Chlor, Brom, Cyan, Nitro, Methylsulfonyl, Phenylsulfonyl oderToluylsulfonyl, Wasserstoff, Chlor oder Brom, Wasserstoff, Chlor, Brom oder Alkylcarbonylamino mit 1 oder 2 Kohlenstoffatomen im Alkylrest, der als Substituenten Chlor oder Brom tragen kann, wobei jedoch zumindest einer der Substituenten R2 und R3 Wasserstoff ist, Wasserstoff, Methoxy oder Äthoxy, unabhängig voneinander, Alkyl mit 1 —4 Kohlenstoffatomen, das Hydroxyl, Cyan, Methoxy, Äthoxy, Acetoxy, Propionyloxy, Butyryloxy, Benzoyloxy, Methoxycarbonyl, Äthoxycarbonyl, Methoxycarbonyloxy oder Äthoxycarbonyloxy als Substituenten tragen kann. Alkyl mit 1 —4 Kohlenstoffatomen, -CO-,-CO-O-oder-SO2-und 2 oder 3Chlorine, bromine, cyano, nitro, methylsulfonyl, phenylsulfonyl or toluylsulfonyl, hydrogen, chlorine or bromine, hydrogen, chlorine, bromine or alkylcarbonylamino with 1 or 2 carbon atoms in the alkyl radical, which can have chlorine or bromine as a substituent, but at least one of the substituents R. 2 and R 3 is hydrogen, hydrogen, methoxy or ethoxy, independently of one another, alkyl with 1-4 carbon atoms which carry hydroxyl, cyano, methoxy, ethoxy, acetoxy, propionyloxy, butyryloxy, benzoyloxy, methoxycarbonyl, ethoxycarbonyl, methoxycarbonyloxy or ethoxycarbonyloxy as substituents can. Alkyl with 1-4 carbon atoms, -CO -, - CO-O- or-SO 2 - and 2 or 3

R7 X η R 7 X η

2. Verfahren zur Herstellung der Azoverbindungen der Foimel gemäß Anspruch 1, dadurch gekennzeichnet, daß man ein Amin der allgemeinen Formel2. A process for the preparation of the azo compounds of the Foimel according to claim 1, characterized in that characterized in that an amine of the general formula

R1 R 1

diazotiert und mit einer Verbindung der allgemeinen Formeldiazotized and with a compound of the general formula

R4 R 4

NH-X— (CH2)„—O—R7 NH-X- (CH 2 ) "- O-R 7

kuppelt, in welchen Formeln Ri, R2, R3, R4, R5, Re, R7, X und η die im Anspruch 1 angegebenen Bedeutungen haben.couples, in which formulas Ri, R 2 , R3, R4, R5, Re, R7, X and η have the meanings given in claim 1.

3. Verwendung der Azofarbstoffe der Formel gemäß Anspruch 1 als Dispersionsfarbstoffe, zum Färben, Klotzen oder Bedrucken von Fasern oder Fäden oder daraus hergestellten Materialien aus voll- oder halbsynthetischen, hydrophoben, hochmolekularen organischen Stoffen.3. Use of the azo dyes of the formula according to claim 1 as disperse dyes for Dyeing, padding or printing of fibers or threads or materials made therefrom fully or semi-synthetic, hydrophobic, high molecular weight organic substances.

Gegenstand der Erfindung sind von Sulfonsäuregruppen freie Verbindungen der 4-Nitro-2'-alkoxyacyIamino-4'-diaDcylamino-l,r-azobenzolreihe, die sich ausgezeichnet als Dispersionsfarbstoffe, zum Färben von Fasern oder Fäden oder daraus hergestellten Materialien aus voll- oder halbsynthetischen, hydrophoben, hochmolekularen organischen Stoffen eignen. Die erhaltenen Färbungen zeichnen sich insbesondere durch ihre Sublimierechtheit, ihr gutes Ziehvermögen und die Farbstärke, aber auch durch ihre Licht- und Naßechtheiten aus.The invention relates to compounds of the 4-nitro-2'-alkoxyacyIamino-4'-diaDcylamino-l, r-azobenzene series which are free from sulfonic acid groups and which are excellent as disperse dyes for dyeing Fibers or threads or materials made from them made of fully or semi-synthetic, hydrophobic, high molecular weight organic substances. The colorations obtained are particularly notable their fastness to sublimation, their good drawability and the Color strength, but also by their light and wet fastness.

Die neuen Farbstoffe entsprechen der allgemeinen FormelThe new dyes correspond to the general formula

R5 R 5

R3 R-.R 3 R-.

=N^ O= N ^ O

NHX(CH2),-OR7 NHX (CH 2 ), - OR 7

worin
Riwherein
Ri

Chlor, Brom, Cyan, Nitro, Methylsulfonyl, Phenylsulfonyl oderToluylsulfonyl,Chlorine, bromine, cyano, nitro, methylsulfonyl, Phenylsulfonyl or toluylsulfonyl,

R2 Wasserstoff, Chlor oder Brom,R 2 is hydrogen, chlorine or bromine, R3 Wasserstoff, Chlor, Brom oder Alkylcarbo-R 3 hydrogen, chlorine, bromine or alkyl carbon

nylamino mit 1 oder 2 Kohlenstoffatomen im Alkylrest, der als Substituenten Chlor oder Brom tragen kann, wobei jedochnylamino with 1 or 2 carbon atoms in the alkyl radical, the substituent being chlorine or can carry bromine, however

zumindest einer der Substituenten R2 und R3 Wasserstoff ist,at least one of the substituents R 2 and R 3 is hydrogen,

R4 Wasserstoff, Methoxy oder Äthoxy,R4 hydrogen, methoxy or ethoxy,

R5 und R6 unabhängig voneinander, Alkyl mit 1-4 Kohlenstoffatomen, das Hydroxyl, Cyan,R 5 and R 6 independently of one another, alkyl with 1-4 carbon atoms, the hydroxyl, cyano,

Methoxy, Äthoxy, Acetoxy, Propionyloxy, Butyryloxy, Benzoyloxy, Methoxycarbonyl, Äthoxycarbonyl, Methoxycarbonyloxy oder Äthoxycarbonyloxy als Substituenten tragen kann,Methoxy, ethoxy, acetoxy, propionyloxy, butyryloxy, benzoyloxy, methoxycarbonyl, Ethoxycarbonyl, methoxycarbonyloxy or ethoxycarbonyloxy can carry as substituents,

Rr Alkyl mit 1 — 4 Kohlenstoffatomen,Rr alkyl with 1 - 4 carbon atoms, X -CO-,-CO-O-oder-SO2-undX -CO -, - CO-O-or-SO 2 -and

ηη 2 oder 32 or 3

sind.are.

Das Verfahren zur Herstellung der neuen Verbindungen ist dadurch gekennzeichnet, daß man ein Amin der allgemeinen FormelThe process for the preparation of the new compounds is characterized in that an amine is used general formula

diazotiert und mit einer Verbindung der allgemeinen Formeldiazotized and with a compound of the general formula

(III)(III)

NH-X—(CH2)„—0—R7 NH-X- (CH 2 ) "- 0-R 7

kuppelt, in welchen Formeln Ri, R2, R3, R4, Rs, Re, R7, und η die oben angegebenen Bedeutungen haben.couples, in which formulas Ri, R 2 , R3, R4, Rs, Re, R7, and η have the meanings given above.

NH2 NH 2

mit einer Säure der Formelwith an acid of the formula

Die DiazotJerung und das Kuppeln werden nach allgemein, zum TeQ über 100 Jahre bekannten Methoden durchgeführtThe diazotization and the domes will follow in general, methods known for the TeQ for over 100 years are carried out

Die Herstellung der Kupplungskomponenten erfolgt nach an sich bekannten Methoden, z. B. indem man ein Ainin der FormelThe coupling components are produced by methods known per se, e.g. B. by a Ainin the formula

toto

1515th

bei Temperaturen zwischen etwa 150° und 2000C unter Wasserabspaftung umsetzt die Nitrogruppe reduziert und die Reste R5 und Re durch Kondensation oder Addition einführtat temperatures between about 150 ° and 200 0 C under Wasserabspaftung the nitro group is reacted reduced and the radicals R5 and Re by condensation or addition introduces

Die Verarbeitung der neuen Verbindungen der Formel I zu Färbepräparaten erfolgt auf allgemein bekannte Weise, z. B. durch Mahlen in Gegenwart von Dispergier- und/oder Füllmitteln. Mit den gegebenenfalls im Vakuum oder durch Zerstäuben getrockneten Präparaten kann man, nach Zugabe von mehr oder weniger Wasser, in sogenannter langer oder kurzer Flotte färben, klotzen oder bedrucken.The processing of the new compounds of the formula I into coloring preparations takes place in a general manner known way, e.g. B. by milling in the presence of Dispersants and / or fillers. With the optionally dried in a vacuum or by atomization After adding more or less water, preparations can be made in so-called long or short form Dye, pad or print liquor.

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-2'/2-acetat, Cellulosetriacetat und synthetischen Polyamiden. Auch Polyolefine lassen sich mit ihnen färben. Man färbt oder bedruckt nach an sich bekannten, z. B. dem in der französischen Patentschrift H 45 371 beschriebenen Verfahren.The dyes are excellent on textile material made of fully synthetic materials from aqueous suspension or semi-synthetic, hydrophobic, high molecular weight organic substances. They are particularly suitable for dyeing or printing textile material linear, aromatic polyesters, as well as cellulose-2 '/ 2-acetate, cellulose triacetate and synthetic polyamides. They can also be used to color polyolefins. One dyes or prints according to known, z. B. that in French patent specification H 45 371 described procedure.

Gegenüber den nächstvergleichbaren, aus den französischen Patentschriften 1382 654 und 14 28 383 bekannten Farbstoffen besitzen die erfindungsgemäßen Farbstoffe, auf Cellulosetriacetatmaterial ausgefärbt Färbungen mit besserer Thermofixier- und TrockenreinigungsechtheitCompared to the next comparable, from French patents 1382 654 and 14 28 383 The dyes according to the invention have known dyes colored on cellulose triacetate material Dyeings with better heat setting and dry cleaning fastness

Im folgenden Beispiel bedeuten die Teile Gewichtsteile, die Temperaturen sind in Celsiusgraden angegeben.In the following example, the parts are parts by weight and the temperatures are given in degrees Celsius.

Beispiel 1example 1

Zu 155 Teilen konzentrierter Schwefelsäure fügt man bei Temperaturen bis maximal 70° 7 Teile Natriumnitrit und anschließend bei 15°, 24,2 Teile 2-Amino-3-brom-5-nitro-benzonitriL Man rührt 2 Stunden bei 15 bis 20°. Die so erhaltene Diazoniumsalzlösung wird dann mit einer Lösung von 2 Teilen Harnstoff und 25 Teilen 1 -N ,N-Diäthylamino-3-{3'-methoxypropinonyl)-anilid in 100 Teilen Eisessig vereinigt Nach Zugabe von 500 Teilen Eiswasser wird noch 2 Stunden gerührt der ausgefallene Farbstoff abfiltriert, mit Wasser säurefrei gewaschen und getrocknet Er färbt Polyesterfasermaterial farbstark in brillant blauen Tönen, mit sehr guten Echtheiten.155 parts of concentrated sulfuric acid are added at temperatures up to a maximum of 70 °, 7 parts of sodium nitrite and then at 15 °, 24.2 parts of 2-amino-3-bromo-5-nitro-benzonitrile, the mixture is stirred for 2 hours at 15 to 20 °. The diazonium salt solution thus obtained is then treated with a solution of 2 parts of urea and 25 parts 1 -N, N-diethylamino-3- {3'-methoxypropinonyl) anilide in 100 parts of glacial acetic acid combined. After adding 500 parts of ice water, the mixture is stirred for a further 2 hours precipitated dye is filtered off, washed acid-free with water and dried. It dyes polyester fiber material strongly in brilliant blue shades, with very good shades Fastnesses.

In der folgenden Tabelle sind weitere, analog dem obigen Beispiel 1 hergestellte Farbstoffe der Formel 1 aneeeeben.The following table contains further dyes of the formula 1 prepared analogously to Example 1 above aneeeeben.

I jj ιI jj ι

2 K "> -3 J .O2 K "> -3 J .O

I I I I I I I I I I I I II I I I I I I I I I I I I I

OOOOOOOOOOOO OOOOOOOOOOOOO O

UUCJUUUUOO U OU UUUCJUUUUOO U OU U

I I I I I I I ! I I I I II I I I I I I! I I I I I

xx3t:*;xx£xxxxxx oooooooouuuuu IMIIIIIIIIi!xx 3 t : *; xx £ xxxxxx oooooooouuuuu IMIIIIIIIIi!

O O U OO O U O

YYIlYYIl

X XX X

Si V,Si V,

χ χχ χ

Y YY Y

U
XU
X

X XX X

UUCj(J IIIIUUCj (J IIII

χ
u χ
u

O U OO U O

I £ . £
J υ S υ
I I S II £. £
J υ S υ
IISI

XXXXXXXXXXXX

χ
u1 χ
u 1

O XO X

ZU UTO U

UO OUO O

£ V, S> Si £ £ ££ V, S> Si £ £ £

UUU SUUU UUUU SUUU U

I I I S I I I II I I S I I I I

(J <J Ü (J(J <J Ü (J

0000
I I I I 0000
IIII

XXXXXX

χ £χ £

U UU U

O OO O

U UU U

X XX X

Z ZZ Z

XXXXXXXXXXÜl IXXXXXXXXXXÜl I

nXXXXoäoäeäüxx χnXXXXoäoäeäüxx χ

ζ ζ ζ <S ö" <5 ö' ö δ δ δ
υ uu«5zzzzzzzζ ζ ζ <S ö "<5 ö ' ö δ δ δ
υ uu «5zzzzzzz

I ü I I I I I I I I II ü I I I I I I I I I

Fortsetzungcontinuation

Bsp. R1 Nr.Example R 1 No.

15 —CN15 —CN

16 H5C6-SO2 16 H 5 C 6 -SO 2

R5 R 5

24 25 .26 27 28 29 30 3124 25 .26 27 28 29 30 31

32 33 34 35 36 37 38 39 ■4032 33 34 35 36 37 38 39 ■ 40

desgl. desgl. desgl. —NOjthe same. the same. the same. -NOj — NOj -NOj- NOj -NOj

-NOj-NOj

-NO2 -NOj-NO 2 -NOj

-NOj-NOj

-NO2 -NO 2

-NOj-NOj

-NOj-NOj

-NO2 -NO 2

Cl Br Cl Cl Cl Br CI Cl ClCl Br Cl Cl Cl Br CI Cl Cl

BrBr HH HH ClCl HH HH ClCl HH HH ClCl HH ClCl HH ClCl HH BrBr HH BrBr HH HH -NOCOCH2CHj-NOCOCH 2 CHj BrBr BrBr ClCl BrBr

Br HBr H

Br HBr H

Br HBr H

Br HBr H

Br HBr H

HH HH HH HH HH HH HH HH HH HH HH HH HH HH HH ClCl HH ClCl

H -OC2H3 H -OC 2 H 3

-OCjH, -OCjH3 -OCjH, -OCjH 3

-OC2H3 -OQH3 -OC 2 H 3 -OQH 3

OCH3OCH3

-OCH3 H-OCH 3 H

-OCH3 -OC2H3 -OC2H3 -OC2H3 -OC2H3 -OC2H3 -OCH 3 -OC 2 H 3 -OC 2 H 3 -OC 2 H 3 -OC 2 H 3 -OC 2 H 3

~~" OQ1H3~~ "OQ1H3

-OC2H,-OC 2 H,

H H H H H H H H HH H H H H H H H H

C2H3 C 2 H 3 -QH3 -QH 3 -CH2CHjOCOCHj-CH 2 CHjOCOCHj -CHjCH2OCOCH3 -CHjCH 2 OCOCH 3 desgl.the same desgl.the same desgl.the same desgl.the same desgl.the same desgl.the same desgl.the same desgl.the same — CHjCHjCN- CHjCHjCN -QH,-QH, desgl.the same desgl.the same -QH3 -QH 3 -QH,-QH, -CH2CH2COOCH3 -CH 2 CH 2 COOCH 3 -CH,-CH, -CH2CHjCOOCjH3 -CH 2 CHjCOOCjH 3 -QH,-QH, -CH2CH2OC2H3 -CH 2 CH 2 OC 2 H 3 -CHjCH1OCHjCH3 -CHjCH 1 OCHjCH 3 -CH2CH2CH3 -CH 2 CH 2 CH 3 -CH2CH2CN-CH 2 CH 2 CN -CH2CH2CH2CH,-CH 2 CH 2 CH 2 CH, -CHjCH2COOC2H.-CHjCH 2 COOC 2 H. -CH2CH2OCOOCH3 -CH 2 CH 2 OCOOCH 3 — CHjCHjCN- CHjCHjCN —CHjCHjOCOOQH,—CHjCHjOCOOQH, -CH2CH2OCOOCjH,-CH 2 CH 2 OCOOCjH, -CHjCH2OCOQ1H,-CHjCH 2 OCOQ 1 H, -CH,-CH, -QH,-QH, -QH,-QH, -QH3 -QH 3 CjH,CjH, -CH,-CH, -CH3 -CH 3 -CH2CH2CH2CH,-CH 2 CH 2 CH 2 CH, —CHjCHjCHjCHj—CHjCHjCHjCHj -CH2CHjCH3 -CH 2 CHjCH 3 -CH2CHjCH3 -CH 2 CHjCH 3 desgl.the same desgl.the same -CH,-CH, -CH,-CH, -QH3 -QH 3 C2H5C2H5 -QH3 -QH 3 -QH,-QH,

ηη XX Nuance uufNuance uuf
Polyesterpolyester UlUl N)N) CH(CHj)2 CH (CHj) 2 22 —CO——CO— blaublue O
QO O
QO CHjCHj 22 —co——Co— blaublue CH3 CH 3 22 —co——Co— blaublue CH(CHj)2 CH (CHj) 2 22 —co——Co— blaublue QH5 QH 5 22 -CO--CO- blaublue CjHjCjHj 22 -CO--CO- blaublue C1HjC 1 Hj 22 —coo——Coo— blaublue C2HjC 2 Hj 22 -SO1--SO 1 - blaublue C2HjC 2 Hj 22 —co——Co— rotstichigreddish
blaublue C2HjC 2 Hj 22 —co——Co— rotstichigreddish
blaublue QH5 QH 5
QH,QH, 22
22 —co—
—co——Co—
—Co— rotstichigreddish
blaublue
rotstichigreddish
blaublue C2H,C 2 H, 22 —co——Co— rotstichigreddish
blaublue CjH.CjH. 22 —co——Co— rotstichigreddish
blaublue QH,QH, 22 -co--co- rotstichigreddish
blaublue QH3 QH 3 22 —co——Co— rotstichigreddish
blaublue QH,QH, 22 —co——Co— rotstichigreddish
blaublue C2H,C 2 H, 22 —coo——Coo— roi-arotroi-arot CjH,CjH, 22 —coo——Coo— rosarotpink C1H,C 1 H, 22 —coo——Coo— rosarotpink QH5 QH 5 22 —coo——Coo— rosarotpink QH5 QH 5 22 —coo——Coo— rosarotpink CH,CH, 22 —coo——Coo— rosarotpink CH,CH, 22 —coo——Coo— rosatotpink red QH5 QH 5 22 -COO--COO- rosarotpink CH,CH, 22 —COO-—COO- rosarotpink

Fortsetzungcontinuation

Bsp. R1 Nr.Example R 1 No.

41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 6041 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Cl Cl Cl -SO2CH3 -NO2 -NO2 -NO3 Cl Cl -NO2 Cl Br Cl -SO2CH3 -SO2CH, Cl — NOj Cl Br ClCl Cl Cl -SO 2 CH 3 -NO 2 -NO 2 -NO 3 Cl Cl -NO 2 Cl Br Cl -SO 2 CH 3 -SO 2 CH, Cl - NOj Cl Br Cl

HH ClCl HH ClCl HH ClCl ClCl HH ClCl HH HH HH HH HH ClCl HH ClCl HH BrBr HH HH HH HH HH HH HH HH HH HH ClCl HH HH HH HH HH HH HH HH HH HH

RaRa R?R? R,.R ,. R- »R- » XX Nuance aufNuance on Pol\ esterPol \ ester HH — CHjCHjCHj- CHjCHjCHj — CHjCHjCH.,- CHjCHjCH., -CH, 2-CH, 2 —COO-—COO- rosarotpink HH -CHjCHjCHjCH,-CHjCHjCHjCH, — CHjCHjCHjCH,- CHjCHjCHjCH, -QH5 2-QH 5 2 —COO-—COO- rosarotpink HH -CH,-CH, -CH3 -CH 3 -CjH, 2-CjH, 2nd —COO-—COO- rosarotpink HH —C,H,—C, H, -CjH5 -CjH 5 -CjH5 2-CjH 5 2 —COO-—COO- violettviolet HH -QH,-QH, — CjH,- CjH, -QH, 2-QH, 2 —COO——COO— violettviolet HH -QH,-QH, -CjH,-CjH, -QH, 2-QH, 2 —COO-—COO- violettviolet HH — CjH,- CjH, — CjH,- CjH, -QH, 2-QH, 2 — COO-- COO- violettviolet HH -CjH,-CjH, -CjH,-CjH, -QH5 2-QH 5 2 —COO-—COO- violettviolet HH -CjH5 -CjH 5 -CjH,-CjH, -CH, 2-CH, 2 — COO—- COO— violettviolet HH -CjH,-CjH, -CjH,-CjH, -CjH5 2-CjH 5 2 —COO-—COO- violettviolet HH -CjH,-CjH, -CjH5 -CjH 5 -CH, 2-CH, 2 —coo——Coo— rosarotpink HH -CjH,-CjH, — CjH,- CjH, -CH, 2-CH, 2 —COO-—COO- rosarotpink HH — CHjCHjCH,- CHjCHjCH, — CHjCHjCHj- CHjCHjCHj -CH, 2-CH, 2 —coo——Coo— rosarotpink HH -CjH,-CjH, -CjH,-CjH, -CH, 2-CH, 2 —coo——Coo— violettviolet HH -CjH,-CjH, -CjH5 -CjH 5 -QH, 2-QH, 2 —coo——Coo— violettviolet HH -CjH,-CjH, -CjH,-CjH, —CHjCHjCH, 2—CHjCHjCH, 2 —coo——Coo— violettviolet HH -CjH,-CjH, -CjH,-CjH, desgl. 2same 2 —coo——Coo— violettviolet HH -QH,-QH, -CjH,-CjH, -CHICH,!; 2-CHICH,!; 2 —coo——Coo— rosarotpink HH C2H5 C 2 H 5 -C2H5 -C 2 H 5 -CHjCHjCHjCH, 2-CHjCHjCHjCH, 2 —coo——Coo— rosarotpink HH — CjH,- CjH, -QH,-QH, — CHjCHICHjI; 2- CHjCHICHjI; 2 —coo——Coo— rosarotpink

K)K)

N)N)

OOOO

OOOO

AnwendungsbeispielApplication example

7 Teile des nach Beispiel 1 hergestellten Farbstoffs werden mit 4 Teilen dinaphthylmethandisulfonsaurem Natrium, 4 Teilen Natriumcetylsulfat und 5 Teilen wasserfreiem Natriumsulfat in einer Kugelmühle 48 Stunden zu einem feinen Pulver gemahlen.7 parts of the dye prepared according to Example 1 are mixed with 4 parts of dinaphthylmethandisulfonsaurem Sodium, 4 parts of sodium cetyl sulfate and 5 parts of anhydrous sodium sulfate in a ball mill 48 Ground to a fine powder for hours.

1 Teil des so erhaltenen Färbepräparats wird mit wenig Wasser angeteigt und die erhaltene Suspension durch ein Sieb einem 2 Teile Natriumlaurylsulfat in 40001 part of the dye preparation obtained in this way is made into a paste with a little water and the suspension obtained through a sieve a 2 parts sodium lauryl sulfate in 4000

Teilen Wasser enthaltenden Färbebad zugesetzt. DasParts of the dyebath containing water were added. That

Flottenverhältnis beträgt 1 :40.
Man gibt nun 100 Teile gereinigtes PolyestergewebeThe liquor ratio is 1:40.
100 parts of cleaned polyester fabric are then added

bei 40-50° in das Bad, gibt 20 Teile eines chlorierten Benzols in Wasser emulgiert zu, erwärmt das Bad langsam auf 100° und färbt 1 -2 Stunden bei 95-100°.at 40-50 ° in the bath, 20 parts of a chlorinated benzene emulsified in water are added, the bath is heated slowly to 100 ° and stains for 1 -2 hours at 95-100 °.

Das blau gefärbte Gewebe wird gewaschen, geseift, erneut gewaschen und getrocknet. Die egale, farbstarkeThe blue colored fabric is washed, soaped, washed again and dried. The level, strong color

Färbung ist ausgezeichnet licht-, überfärbe-, wasch-, ίο wasser-, meerwasser-, schweiß-, sublimier-, rauchgas-, thermofixier-, plissier- und permanent-preßecht.Coloring is excellent light, overdyeing, washing, ίο water, sea water, perspiration, sublimation, smoke gas, thermosetting, pleating and permanent press-proof.

Claims (1)

Patentansprüche:Patent claims: 1. Die Monoazoverbindungen der allgemeinen Formel1. The monoazo compounds of the general formula worinwherein P.-und R6 P. and R 6 NH-X—(CH2),-O—R7 NH-X- (CH 2 ), - O-R 7
DE19712120877 1970-05-06 1971-04-28 Monoazo compounds sparingly soluble in water, process for their preparation and their use Expired DE2120877C3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH680870A CH526615A (en) 1970-05-06 1970-05-06 Disperse azo dyes for hydrophobic materials esp aromatic polyesters
CH1924970 1970-12-29

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DE2120877A1 DE2120877A1 (en) 1971-11-25
DE2120877B2 true DE2120877B2 (en) 1979-07-19
DE2120877C3 DE2120877C3 (en) 1980-03-20

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DE19712120876 Pending DE2120876A1 (en) 1970-05-06 1971-04-28 Azo compounds that are sparingly soluble in water, their production and use

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JP (1) JPS5426575B1 (en)
BE (2) BE766773A (en)
CA (2) CA925856A (en)
CY (1) CY882A (en)
DD (1) DD95069A5 (en)
DE (2) DE2120877C3 (en)
ES (2) ES390851A1 (en)
FR (2) FR2088375B1 (en)
GB (2) GB1352059A (en)
HK (1) HK79876A (en)
KE (1) KE2681A (en)
MY (1) MY7700100A (en)
NL (2) NL7106130A (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4042580A (en) * 1970-05-06 1977-08-16 Sandoz Ltd. Phenylazophenyl dyes having an alkoxyacylamino group on the coupling component radical
US4038269A (en) * 1970-05-06 1977-07-26 Sandoz Ltd. 2'-alkoxyacylamino-4'-alkylamino-4-nitro-1,1'-azobenzene disperse dyes
US4667023A (en) * 1973-07-16 1987-05-19 Sandoz Ltd. 4-(2'-halo-4'-nitrophenylazo)-2-2[2'-(C1-2 alkoxy or 2"-methoxyethoxy)ethoxycarbonylamino --N,N-di-C2-3 alkylanilines
GB1565531A (en) * 1976-02-05 1980-04-23 Ici Ltd Diperse monoazo dyestuffs
US4076706A (en) * 1976-11-15 1978-02-28 Eastman Kodak Company Disperse dyes from 2-cyano-4,6-dinitroaniline and selected 2(2'-alkoxy-5'-acylamidoanilino)alkanes
LU76960A1 (en) * 1977-03-16 1978-10-18
CH633307A5 (en) * 1977-03-16 1982-11-30 Ciba Geigy Ag AZO DYES.
LU78553A1 (en) * 1977-11-21 1979-06-13 Ciba Geigy Ag MONOAZO DYES, METHOD OF MANUFACTURING AND USE
IT1122520B (en) * 1978-09-08 1986-04-23 Ici Ltd DYES

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1167704A (en) * 1955-07-13 1958-11-28 Sandoz Ag Water-insoluble mono-azo dyes, process for their preparation and applications
CH343560A (en) * 1956-07-21 1959-12-31 Sandoz Ag Process for the preparation of water-insoluble monoazo dyes
FR1383356A (en) * 1963-02-21 1964-12-24 Ciba Geigy Water-insoluble monoazo dyes and process for obtaining them
FR1361809A (en) * 1963-07-08 1964-05-22 Bayer Ag Monoazo dyes and their manufacturing process
FR1377496A (en) * 1963-09-24 1964-11-06 Ici Ltd New disperse dyes
CH465089A (en) * 1964-03-13 1968-11-15 Sandoz Ag Process for the preparation of monoazo dyes
FR1486349A (en) * 1965-07-12 1967-06-23 Sandoz Sa Azo dyes, their manufacturing process and applications

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CA925856A (en) 1973-05-08
MY7700100A (en) 1977-12-31
GB1349003A (en) 1974-03-27
DE2120877C3 (en) 1980-03-20
BE766772A (en) 1971-10-01
GB1352059A (en) 1974-05-15
CY882A (en) 1977-03-18
BE766773A (en) 1971-10-01
ES390851A1 (en) 1974-08-01
JPS5426575B1 (en) 1979-09-05
KE2681A (en) 1976-12-24
NL7106129A (en) 1971-11-09
FR2088374B1 (en) 1975-08-22
ES390852A1 (en) 1974-08-01
FR2088375A1 (en) 1972-01-07
DD95069A5 (en) 1973-01-12
CA925857A (en) 1973-05-08
FR2088374A1 (en) 1972-01-07
FR2088375B1 (en) 1975-07-04
NL7106130A (en) 1971-11-09
HK79876A (en) 1976-12-24
DE2120876A1 (en) 1971-11-25
DE2120877A1 (en) 1971-11-25

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