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DE2716033A1 - ACID AZO DYES - Google Patents

ACID AZO DYES

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Publication number
DE2716033A1
DE2716033A1 DE19772716033 DE2716033A DE2716033A1 DE 2716033 A1 DE2716033 A1 DE 2716033A1 DE 19772716033 DE19772716033 DE 19772716033 DE 2716033 A DE2716033 A DE 2716033A DE 2716033 A1 DE2716033 A1 DE 2716033A1
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DE
Germany
Prior art keywords
alkyl
formula
hydrogen
blue
chlorine
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
Application number
DE19772716033
Other languages
German (de)
Inventor
Heinz Dipl Chem Dr Eilingsfeld
Guenter Dipl Chem Dr Hansen
Guenther Dipl Chem Dr Seybold
Georg Zeidler
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BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DE19772716033 priority Critical patent/DE2716033A1/en
Priority to IT21636/78A priority patent/IT1095370B/en
Priority to FR7809681A priority patent/FR2386585A1/en
Priority to JP4134378A priority patent/JPS53126034A/en
Publication of DE2716033A1 publication Critical patent/DE2716033A1/en
Pending 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3665—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms
    • C09B29/3669—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms from a pyrimidine ring
    • C09B29/3673—Barbituric acid and derivatives thereof
    • 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
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
    • C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
    • C09B29/0081—Isothiazoles or condensed isothiazoles
    • 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
    • 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
    • C09B29/065—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group containing water solubilizing 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
    • 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
    • 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
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C09B29/3656—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing amino-1,2-diazoles

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

O.Z. 32O.Z. 32

Saure AzofarbstoffeAcid azo dyes

Die Erfindung betrifft Verbindungen, die in Form der freien Säuren der Formel IThe invention relates to compounds which, in the form of the free acids of the formula I

Y SOJi Y SOJi

χ, ι ζ χ , ι ζ

I,I,

N=N-K
entsprechen,N = NK
correspond,

in derin the

X Wasserstoff, Chlor, Brom, Cyan, Nitro, C1- bis C^-Alkyl, C1- bis C^-Alkoxy, C- bis C^-Alkylmercapto, Alkylsulfonyl, Alkylsulfinyl, Alkanoyl, Benzoyl, Carboxyl, Di-C1- bis C^-alkylamino, NHCO-C1-bis Cj,-Alkyl, Hydroxy sulfonyl oder gegebenenfalls substituiertes Carbamoyl oder Sulfamoyl,X hydrogen, chlorine, bromine, cyano, nitro, C 1 - to C ^ -alkyl, C 1 - to C ^ -alkoxy, C- to C ^ -alkyl mercapto, alkylsulfonyl, alkylsulfinyl, alkanoyl, benzoyl, carboxyl, di-C 1 - to C ^ -alkylamino, NHCO-C 1 -bis Cj, -alkyl, hydroxy sulfonyl or optionally substituted carbamoyl or sulfamoyl,

K einen Rest der FormelnNo remainder of the formulas

HO5SHO 5 S

2 V 2 V

8098A2/01898098A2 / 0189

OHOH

(HD-S)(HD-S)

H3C CHH 3 C CH

h$Xh $ X

NHRNHR

oderor

HO3SHO 3 S

H,H,

ι 7ι 7

r'r '

HO R-HO R-

E Wasserstoff, Methyl, Methoxy oder Äthoxy, B2 Wasserstoff, Chlor, Methyl, Äthyl, Benzyl, Sulfobenzyl, Methoxy, E hydrogen, methyl, methoxy or ethoxy, B 2 hydrogen, chlorine, methyl, ethyl, benzyl, sulfobenzyl, methoxy,

Äthoxy, SO H oder Acylamino,
B^ Wasserstoff, C1- bis C -Alkyl, C- oder C,-Hydroxy- oder Dihydroxyalkyl, Ö-Sulfoäthyl, γ-Sulfopropyl, ß-Cyanäthyl, ß-Hydroxy-Y-chlorpropyl, C,- bis C.-Alkoxyäthyl, Acetoxyäthyl,Ethoxy, SO H or acylamino,
B ^ hydrogen, C 1 - to C -alkyl, C- or C, -hydroxy- or dihydroxyalkyl, Ö-sulfoethyl, γ-sulfopropyl, ß-cyanoethyl, ß-hydroxy-Y-chloropropyl, C, - to C.- Alkoxyethyl, acetoxyethyl,

• 4• 4

ß-Chloräthy1, y-Amino- oder -Acetylaminopropyl, ß-Carboxyfithyl, ß-Carbamoyläthyl, Benzyl, Sulfobenzyl, Phenyläthyl, Sulfophenyläthyl oder Cyclohexyl,
B4 C1- bis C.-Alkyl, C0- oder C,-Hydroxyalkyl, ß-Cyanäthyl, ß-Chlor-ß-Chloräthy1, ß-Amino- or -Acetylaminopropyl, ß-Carboxyfithyl, ß-Carbamoyläthyl, Benzyl, Sulfobenzyl, Phenyläthyl, Sulfophenyläthyl or Cyclohexyl,
B 4 C 1 - to C-alkyl, C 0 - or C, -hydroxyalkyl, ß-cyanoethyl, ß-chlorine

äthyl, C.,- bis C -Alkoxyäthyl, Benzyl oder Sulfobenzyl, > 4ethyl, C., - to C -alkoxyethyl, benzyl or sulfobenzyl, > 4

b5 Amino, Acetylamino, Chloracetylamino, Phenoxyacetylamino, Benzoylamino, Chlorbenzoylamino oder Dichlorbenzoylamino,b5 amino, acetylamino, chloroacetylamino, phenoxyacetylamino, benzoylamino, Chlorobenzoylamino or dichlorobenzoylamino,

B Methyl, Chlormethyl, Phenyl, Chlorphenyl oder Acetylamino, B' C1- bis Cg-Alkyl, Cp- oder C,-Hydroxyalkyl, Phenyl-C,- bis C.-B methyl, chloromethyl, phenyl, chlorophenyl or acetylamino, B 'C 1 - to Cg-alkyl, Cp- or C, -hydroxyalkyl, phenyl-C, - to C.-

Alkyl, Cyclohexyl oder Phenyl, ■ die Zahlen 0, 1 oder 2 und
η die Zahlen 1 oder 2 bedeuten.Alkyl, cyclohexyl or phenyl, ■ the numbers 0, 1 or 2 and
η denote the numbers 1 or 2.

-6--6-

809842/0189809842/0189

Einzelne Reste X sind neben den bereits genannten z. B.: CH , CpH , C3H7, C4K9, CH3S, C2H5-S, C3H7-S, C4H9-S, CH3SO2, C2U5SO2, C4H9SO2, CH3SO , CH3O, C2H5O, C3II7O, C4H9O, N(CH3J2, N(C2U5J2,Individual radicals X are in addition to the z. E.g .: CH, CpH, C 3 H 7 , C 4 K 9 , CH 3 S, C 2 H 5 -S, C 3 H 7 -S, C 4 H 9 -S, CH 3 SO 2 , C 2 U 5 SO 2 , C 4 H 9 SO 2 , CH 3 SO, CH 3 O, C 2 H 5 O, C 3 II 7 O, C 4 H 9 O, N (CH 3 J 2 , N (C 2 U 5 J 2 ,

N(c/Hq)o» CONH , CONIICH , CONHC H1-, CONHC ,H7, CONHC.H , ' 2 5 / ν N ( c / H q) o »CONH, CONIICH, CONHC H 1 -, CONHC, H 7 , CONHC.H, '2 5 / ν

P Π MUP U Π U J PΠNf PTf )P Π MUP U Π U J PΠNf PTf)

C4H9 2^C 4 H 9 2 ^

C0n'~~\ , COlQ) oder CON^Jf-CH2CH OH sowie die entsprechendenC0n '~~ \, COlQ) or CON ^ Jf-CH 2 CH OH and the corresponding

Ji \.Ji \.

Sulfamoylreste und CH7Co, ILC ,CO, nc CO, -■* ,CHCO aier H ,C CO. Sulfamoyl radicals and CH 7 Co, ILC, CO, nc CO, - ■ *, CHCO aier H, C CO.

1 - I '» H1C.,- 11 5 1 - I '»H 1 C., - 11 5

Acylaminoreste R sind beispielsweise C- bis C -Alkylcarbonylamino, das noch durch Chlor, Hydroxy oder Carboxyl substituiert sein kann, gegebenenfalls substituiertes Benzoylamino oder C,- bis C.-Alkyl-Acylamino radicals R are, for example, C to C alkylcarbonylamino, which can be substituted by chlorine, hydroxy or carboxyl, optionally substituted benzoylamino or C, - to C-alkyl

L IL ιL IL ι

aminocarbonylamino, r>owU· k.y^^i ^~-i A^-r^ > i aminocarbonylamino, r> owU · k . y ^^ i ^ ~ -i A ^ -r ^> i

fj ' N J oier Ii T1 | " a' ' O 0fj 'NJ oier Ii T 1 | " a " O 0

Im einzelnen seien beispielsweise aufgeführt: NHCHO, NHCOCH , NHCOC2H5, NHCOC H7, NHCOC4H , NHCOCH 2 5 , NHCOCH0Cl, NHCOCHCl0, NHCOCH0OH, NHCOCH0OCH,, NHCH0CH0COOH NHCOCH=CU-COOh, NHCOC=C-COOH, NHCONH2, NHCONHCH , NHCONHC H ,Examples include: NHCHO, NHCOCH, NHCOC 2 H 5 , NHCOC H 7 , NHCOC 4 H, NHCOCH 2 5 , NHCOCH 0 Cl, NHCOCHCl 0 , NHCOCH 0 OH, NHCOCH 0 OCH ,, NHCH 0 CH 0 COOH NHCOCH = CU-COOh, NHCOC = C-COOH, NHCONH 2 , NHCONHCH, NHCONHC H,

NHCONEC H , NHCOC6H , NHCOC6H Cl, NHCOC6H COOH oder NHCOC6H SO3H.NHCONEC H, NHCOC 6 H , NHCOC 6 H Cl, NHCOC 6 H COOH or NHCOC 6 H SO 3 H.

Einzelne Alkyl- und Alkoxyalkylreste für fi und R sind beispielsweise: CH3, C2H5, C3H7, C4U9, C2H4OCH3, C2II4OC2H5, C2H4OC3H7 Individual alkyl and alkoxyalkyl radicals for fi and R are, for example: CH 3 , C 2 H 5 , C 3 H 7 , C 4 U 9 , C 2 H 4 OCH 3 , C 2 II 4 OC 2 H 5 , C 2 H 4 OC 3 H 7

oder C-H.OC ,IL7.
2 4 4 7 or CH.OC, IL 7 .
2 4 4 7

-J--J-

809842/0189809842/0189

ORIGINAL INSPECTEDORIGINAL INSPECTED

·/ υ...:. ^ μ91· / Υ ...:. ^ μ91

Für R sind neben den bereits einzelnen genannten Resten zu erwähnen:For R, in addition to the individual residues already mentioned, the following should be mentioned:

, C4H9 , C 4 H 9

f% TT /t TT ^% TT rt TT f"1 ΓΤ /^t TJ /*| Tl Al TJ f% T] ^^ ^ f% TT / t TT ^% TT rt TT f "1 ΓΤ / ^ t TJ / * | Tl Al TJ f% T] ^^ ^

0,H1-CH9, C^-H1-C9H., CaU-CE-CH0, C,II C H. oder C,H C Π .0, H 1 -CH 9 , C ^ -H 1 -C 9 H., CaU-CE-CH 0 , C, II C H. or C, HC Π.

CH5 CH 5

Zur Herstellung der Verbindungen der Formel I kann man eine Diazoverbindung von Aminen der Formel II
Y SO ,HTo prepare the compounds of the formula I, a diazo compound of amines of the formula II can be used
Y SO, H

II.II.

mit einer Kupplungskomponente der Formel IIIwith a coupling component of the formula III

HK III,
umsetzen, X und K haben dabei die angegebenen Bedeutungen.HK III,
implement, X and K have the meanings given.

Von besonderer technischer Bedeutung sind Verbindungen der Formel I aCompounds of the formula I a are of particular industrial importance

N=N-K1 N = NK 1

in derin the

X Wasserstoff, Chlor, Brom, Carboxyl oder Hydroxysulfonyl und K einen Rest der FormelX is hydrogen, chlorine, bromine, carboxyl or hydroxysulfonyl and No remainder of the formula

-b-809842/0189 -b-809842/0189

bedeuten.mean.

N 2 V N 2 V

-X-X

oderor

CZ. 32 491CZ. 32 491

Bevorzugte Reste sind dabei für:Preferred residues are for:

R Wasserstoff, Methyl, Chlor, Acylamino oder SO,H;R is hydrogen, methyl, chlorine, acylamino or SO, H;

R5 und R4 C1- bis C -Alkyl, C^ OH, CH2CHOHCH5,R 5 and R 4 C 1 - to C -alkyl, C ^ OH, CH 2 CHOHCH 5 ,

CH2-CH2-OCOCH3, CH2CH2Cl, CH2CH2CN, CCH 2 -CH 2 -OCOCH 3 , CH 2 CH 2 Cl, CH 2 CH 2 CN, C

CH0CH0OCHx, C0H-OC0H1-, 0,H^NHCOCH7. oder CH0C.H.SO,H; R1 Wasserstoff, Methoxy oder Methyl.CH 0 CH 0 OCH x , C 0 H-OC 0 H 1 -, 0, H ^ NHCOCH 7 . or CH 0 CHSO, H; R 1 is hydrogen, methoxy or methyl.

Bevorzugte Acylaminoreste R sind z. B.: COCH , COCH--OH, COCOOH, COCH2-CH2-COOH.Preferred acylamino radicals R are, for. E.g .: COCH, COCH - OH, COCOOH, COCH 2 -CH 2 -COOH.

Die Farbstoffe der Formel I sind rot bis grünblau und eignen sich insbesondere zum Färben von natürlichen und synthetischen Polyamiden, wie Wolle, Polyamid-6 und -6,6, sowie Pelzen.The dyes of the formula I are red to green-blue and are particularly suitable for dyeing natural and synthetic polyamides, such as wool, polyamide-6 and -6,6, and furs.

Man erhält Färbungen mit sehr guten Echtheiten, von denen die Licht- und Naßechtheiten, wie Wasch-, Wasser-, Schweiß-, Walk- und Seewasserechtheiten hervorzuheben sind. Die Farbstoffe haben zudem eine sehr hohe Farbstärke. Bei den Pelzfärbungen ist die gute Bügelechtheit und Kombinierbarkeit zu Braun- und Schwarztönen hervorzuheben. The dyeings obtained have very good fastness properties, of which the light and wet fastness properties, such as wash, water, perspiration, milled and sea water fastnesses are to be emphasized. The dyes also have a very high color strength. The fur dyeings are easy to iron and can be combined with brown and black tones .

In den folgenden Beispielen beziehen sich die Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht. In the following examples, the data on parts and percentages, unless otherwise stated, are by weight.

809842/0189809842/0189

-9--9-

Beispiel example 11

2J Teile 3-Aminobenzisothiazol-7-sulfonsäure werden in 200 Teilen Wasser mit 4»θ Teilen Ätznatron gelöst und nach Zugabe einer Lösung von 6,9 Teilen Natriumnitrit unter Rühren in eine Mischung aus 200 Tei len Eis und 46,4 Teilen 32 /jiger Salzsäure getropft. Die Suspension des Diazoniumsalzes wird ca. 1 Stunde bei 0 - 5 °C gerührt, worauf man den Nitritüberschuß mit wenig Amidosulfonsäure zerstört. Danach gibt man eine wäßrige Lösung von 21,63 Teilen 3-(N,N-Diäthylamino)-acetylaminobenzol in 100 Teilen Wasser und 11,6 Teilen 32 %iger Salzsäure zu. Nach ca. 15 Minuten langem Rühren wird der pH-Wert mit einer Lösung von 57t5 Teilen Natriumacetat auf 4-5 eingestellt. Las Re ak- tionsgemisch wird bis zum Ende der Kupplung weiter gerührt und der Farbstoff abgesaugt. Nach dem Trocknen bei 70 °C unter vermindertem Druck erhält man ein dunkles Pulver der Formel 2J parts of 3-aminobenzisothiazole-7-sulfonic acid are dissolved in 200 parts of water with 4 » θ parts of caustic soda and, after adding a solution of 6.9 parts of sodium nitrite, with stirring, in a mixture of 200 parts of ice and 46.4 parts of 32 / jiger Hydrochloric acid dripped. The suspension of the diazonium salt is stirred for about 1 hour at 0-5 ° C., after which the excess nitrite is destroyed with a little sulfamic acid. An aqueous solution of 21.63 parts of 3- (N, N-diethylamino) acetylaminobenzene in 100 parts of water and 11.6 parts of 32% strength hydrochloric acid is then added. After stirring for about 15 minutes, the pH is adjusted to 4-5 with a solution of 57-5 parts of sodium acetate. The reaction mixture is stirred further until the coupling has ended and the dye is suctioned off. After drying at 70 ° C. under reduced pressure, a dark powder of the formula is obtained

das sich in Wasser mit rotstichig blauer Farbe löst und auf Polyamid 6, Pelzen, Wolle und Leder rotstichig blaue Färbungen von hohem Echtheitsniveau gibt. which dissolves in water with a reddish blue color and gives reddish blue dyeings with a high level of fastness to polyamide 6, fur, wool and leather.

Analog dem Beispiel 1 werden die in der nachfolgenden Tabelle auf geführten Farbstoffe mit ähnlichen coloristiechen Eigenschaften hergestellt. The products listed in the table below to dyes with similar properties coloristiechen be prepared analogously to Example. 1

-10--10-

809842/0189809842/0189

4040

DiazokomponenteDiazo component

Kupplungskomponente Farbton auf Polyamid 6Coupling component color on polyamide 6

SO H SO H

NH9 NH 9

SO1HSO 1 H

NH,NH,

C9II^OCOCH, /24C 9 II ^ OCOCH, / 24

/C2H5/ C 2 H 5

C2H5 C 2 H 5

/C3H7/ C 3 H 7

C5H7 C 5 H 7

N Y- NN Y- N

blaublue

violettviolet

blau, rotstichigblue, reddish

blau, rotstichigblue, reddish

809842/0189809842/0189

-11--11-

Nr.No.

DiazokomponenteDiazo component

KupplungskomponenteCoupling component

Farbton auf PolyamidColor on polyamide

1010

1313th

SO ,HSO, H

NH,NH,

CH,CH,

CH OhCH Oh

H3?° C.H H 3? ° CH

/C2H5/ C 2 H 5

NHCOCH2CH2COOhNHCOCH 2 CH 2 COOh

blau, rotstichigblue, reddish

blaublue

blau, rotstichigblue, reddish

blaublue

809842/0189809842/0189

U.Z. 3U.Z. 3

Nr.No.

BiazokomponenteBio component

KupplungskomponenteCoupling component

Farbton auf PolyamidColor on polyamide

/C2H4OCE3/ C 2 H 4 OCE 3

C2E4ClC 2 E 4 Cl

ΛΗ5Λ Η 5

CoH.C00CHa 24 5C o H.C00CH a 24 5

CH,CH,

C2E5 C 2 E 5

ΛΗ5Λ Η 5

°2E5° 2 E 5

NHCOC - CCOOH I ι
Cl ClNHCOC - CCOOH I ι
Cl Cl

blau, rotstichigblue, reddish

blau blau, rotstichigblue blue, reddish tinged

violettviolet

blaublue

8098A2/01898098A2 / 0189

S-S-

ο.ζ. yd 491ο.ζ. yd 491

Hr.Mr.

DiazokomponenteDiazo component

KupplungskomponenteCoupling component

Farbton auf PolyamidColor on polyamide

2323

S03? S0 3?

KRrKRr

HH,HH,

SO, HSO, H

2424

NH,NH,

NHCONH,NHCONH,

HHCOGH2ClHHCOGH 2 Cl

C2H4CONH2 C 2 H 4 CONH 2

NHCOCHgCHgCOOHNHCOCHgCHgCOOH

blau, rotstichigblue, reddish

▼iolett▼ iolett

blau, rotstichigblue, reddish

809842/0189809842/0189

DiazokomponenteDiazo component

Kupplungskomponente Farbton auf Polyamid 6Coupling component color on polyamide 6

NH,NH,

C9H-OCH, /24 3C 9 H-OCH, / 24 3

C_H.OCH, OCH 2 4 3 C_H.OCH, OCH 2 4 3

C0H-COOH <i 4 C 0 H-COOH <i 4

H1CO U H 1 CO U

NHCOCHNHCOCH

NHCO// \\ SO H NHCO // \\ SO H

π w w H2N N blau, rotstichig π ww H 2 N N blue, tinged red

violettviolet

blau, grünstichigblue, greenish tinge

dunkelblaudark blue

rotRed

809842/0189809842/0189

O. Z. $2 -191OZ $ 2 -191

Beispiel 50Example 50

23 Teile 3-Aminobenzisothiazol-7-sulfonsäure werden analog dem Beispiel 1 diazotiert. Anschließend fügt man zu der Suspension des Diazoniumsalzee eine neutrale Lösung von 30,1 Teilen 1-(4-Toluidino)-naphthalin-8-sulfonsäure in 100 Teilen Wasser zu. Der Ansatz wird dann mit Natriumacetat auf einen pH-Wert von 4-5 eingestellt und bis zum Ende der Kupplung weiter gerührt. Der Farbstoff von der Zusammensetzung23 parts of 3-aminobenzisothiazole-7-sulfonic acid are diazotized analogously to Example 1. A neutral solution of 30.1 parts of 1- (4-toluidino) -naphthalene-8-sulfonic acid in 100 parts of water is then added to the suspension of the diazonium salt. The batch is then adjusted to a pH of 4-5 with sodium acetate and stirred further until the coupling has ended. The dye from the composition

SO3BSO 3 B

ς\ ,γ- So5Hς \ , γ- So 5 H

wird mit 160 Teilen Natriumchlorid ausgesalzen, abgesaugt und bei 70 0C getrocknet. Er färbt Polyamid 6, Wolle sowie Pelz in echten, brillanten, grünstichigen Blautönen. is salted out, suction filtered and dried at 70 0 C with 160 parts of sodium chloride. It dyes polyamide 6, wool and fur in real, brilliant, greenish shades of blue.

Die in der nachfolgenden Tabelle zusammengefaßten Farbstoffe lassen eich nach dem Beispiel 30 darstellen, wobei die Kupplungskomponenten der Beispiele 31 - 40 in verdünnter Salzsäure gelöst werden.The dyes summarized in the table below leave calibrate according to example 30, the coupling components of Examples 31-40 can be dissolved in dilute hydrochloric acid.

-lo--lo-

809842/0189809842/0189

ü.z. 32 491ü.z. 32 491

Nr.No.

DiazokomponenteDiazo component

KupplungskomponenteCoupling component

Farbton auf Polyamid Color on polyamide

NELNEL

NH,NH,

30 H30 H.

rr\rr \

NE,NE,

/C2H40H / C 2 H 4 OH

C2E5 C 2 E 5

C9H-OH /24C 9 H-OH / 24

OH, CB5OH, CB 5

/C2H5/ C 2 H 5

°2H5 NHCOCOOH ° 2 H 5 NHCOCOOH

NHCOCH2OCH3 NHCOCH 2 OCH 3

OCH3 C2H5OCH 3 C 2 H 5

/C2H40H / C 2 H 4 OH

CH3 C2E5CH 3 C 2 E 5

blau, rotstichigblue, reddish

blaublue blaublue blau,rotstichigblue, reddish

8098A2/01898098A2 / 0189

ο.ζ. 32 491ο.ζ. 32 491

MX,MX,

DiazokomponenteDiazo component

KupplungskomponenteCoupling component

Farbton auf Polyamid Color on polyamide

4343

SO5HSO 5 H

HH,HH,

ΛΗ40Η Λ Η 4 0Η

violettviolet

ClCl

OH IOH I

-N-N

CH2CH-CH2-OHCH 2 CH-CH 2 -OH

blau, rotstichigblue, reddish

fH f H

C4H9 C 4 H 9

'C2H5 'C 2 H 5

MHCOHHC.HQ 4 7MHCOHHC.H Q 4 7

/CH5/ CH 5

SO3H CH3SO 3 H CH 3

/0A/ 0 A

CH2-CH2-CH2SO3HlCH 2 -CH 2 -CH 2 SO 3 Hl

809842/0189809842/0189

Diazokomponente KupplungskomponenteDiazo component coupling component

O.Z. 32 491O.Z. 32 491

Farbton auf PolyamidColor on polyamide

NH,NH,

NH,NH,

NH,NH,

SO ,HSO, H

NH,NH,

OH NHCOCH,OH NHCOCH,

-CH,-CH,

ir50?ir 50 ?

OH NHCO-OH NHCO-

HO SHO S

SO HSO H

HO NHCO-/'HO NHCO- / '

SO HSO H

Cl HO NHCO-& Cl HO NHCO - &

SO5HSO 5 H

SO5H blau, grünstichigSO 5 H blue, greenish tinge

rotstichigreddish

blaublue

blaublue

blau, rotstichigblue, reddish

-19--19-

809842/0189809842/0189

O.Z. $2 491OZ $ 2,491

Diazokomponente Kupplungskomponente Diazo component coupling component

Farbton auf PolyamidColor on polyamide

HH,HH,

-N-N

HO5SHO 5 S

NHCOCH,NHCOCH,

OHOH

C2H4OSO5HC 2 H 4 OSO 5 H

OHOH

LCOLCO

SO,!! SO3HSO,!! SO 3 H

OH MHOH MH

SO HSO H

C2H5 blau, rotstichig C 2 H 5 blue, reddish tinged

blaublue

blau, rotstichigblue, reddish blaublue

dunkelblau, rotstichigdark blue, reddish violettviolet

-20--20-

809842/0189809842/0189

Kr.Kr.

DiazokomponenteDiazo component

KupplungskomponenteCoupling component

CZ. 32CZ. 32

Farbton auf Polyanid 6Color shade on polyanide 6

SO HSO H

SO H SO H

SO HSO H

blau, rotstichigblue, reddish

η ηη η

-21--21-

809842/0189809842/0189

2Λ2Λ

Beispiel 59Example 59

o.z. yi 491 2716033o. z. yi 491 2716033

23 Teile J-AminobenziBothiazol-Y-sulfonsäure werden wie in Beispiel 1 diazotiert dann fügt man zur Suspension des Diazoniumsalzeβ eine wäßrige salzsäure Lösung von 25 Teilen 3-(N,M-Dihydroxyäthy1amino)-acetylaaino-ϋβηζοΐ hinzu. Nachdem die Kupplung beendet ist, dampft man die FarbetofflÖBung zur Trockne ein. Bas erhaltene Pulver der Formel23 parts of J-aminobenzi-thiazole-Y-sulfonic acid are obtained as in Example 1 diazotized, an aqueous hydrochloric acid solution of 25 parts of 3- (N, M-dihydroxyäthy1amino) -acetylaaino-ϋβηζοΐ is then added to the suspension of the diazonium salts. After the coupling is finished, you steam the Dye solution to dry. Bas obtained powder of the formula

HNCOCH3 C2H40H HNCOCH 3 C 2 H 4 OH

färbt Polyamid 6, Volle sowie Pelz in klaren, echten Dunkelblautönen.dyes polyamide 6, solid and fur in clear, genuine dark blue tones.

Sie in der nachfolgenden Tabelle zusammengefaßten Farbstoffe lassen sich nach dem Beispiel 59 darstellen.You leave the dyes summarized in the table below can be represented according to example 59.

809842/0189809842/0189

u.Z. j5^ ^)I uZ j5 ^ ^) I

Nr.No.

DiazokomponenteDiazo component

KupplungskomponenteCoupling component

Farbton auf PolyamidColor on polyamide

SO,HSO, H

NH,NH,

SO HSO H

CHCH

ΛΗ 4 0Η Λ Η 4 0Η

C,H,0H 2 4 C, H, OH 2 4

ΛΗ40Η Λ Η 4 0Η

Cl C2H40H Cl C 2 H 4 OH

/C2H40H / C 2 H 4 OH

OCH.OCH.

C2H4OHC 2 H 4 OH

ClCl

C0H-OH /24C 0 H-OH / 24

HNCOCH C2H4OH HNCOCH C 2 H 4 OH

OCH,OCH,

HNCOCHHNCOCH

C2H4OHC 2 H 4 OH

blau, rotstichigblue, reddish

violettviolet

blau, rotstichigblue, reddish

blaublue

dunkelblaudark blue

809842/0189809842/0189

O.Z. j52O.Z. j52

Hr. Diazokomponente Kupplungskomponente Mr. Diazo component coupling component

Farbton auf Polyamid 6 Color on polyamide 6

SO HSO H

C_H.0H HNCOCH2Cl2 C_H.0H HNCOCH 2 Cl 2

SO H SO H

CH9-CH-CH,CH 9 -CH-CH,

r ί \ Jr ί \ J

OHOH

Oh2-CH-CH OH Oh 2 -CH-CH OH

blau, rotstichigblue, reddish

violettviolet

Analok Beispiel 1 werden auch die folgenden Farbstoffe hergestellt:In the same way as in Example 1, the following dyes are also produced:

SO3HSO 3 H

NH,NH,

0 Wn CH3 0 Wn CH 3

HCH3H CH 3

blaublue

-24--24-

809842/0189809842/0189

Nr. Diazokomponente KupplungskomponenteNo. Diazo component Coupling component

o.z. 32 491o.z. 32 491

Farbton auf Polyamid 6Color on polyamide 6

SO5HSO 5 H

üU-*HüU- * H

NH,NH,

blau, rotstichigblue, reddish

, NHC2H4OH, NHC 2 H 4 OH

NHC6H4CH3(P)NHC 6 H 4 CH 3 (P)

NHCOCHNHCOCH

NHCOC2HNHCOC 2 H

SO3HNHC6H4CH (p)SO 3 HNHC 6 H 4 CH (p)

χ Die Kupplungskomponente wird in der erforderlichen Menge Acetonχ The coupling component is acetone in the required amount

gelöst.solved.

BASF Aktiengesellschaft ■BASF Aktiengesellschaft ■

809842/0189809842/0189

Claims (4)

Unsei· Zeicnen: O.Z. j>2 491 Bg/ah ■j : OG Ludwigshaf en, 25.03.1977 PatentansprücheUnsei Draw: O.Z. j> 2 491 Bg / ah ■ j: OG Ludwigshafen, 25.03.1977 patent claims 1. Saure Azofarbstoffe, die in Form der freien Säuren der Formel1. Acid azo dyes, which are in the form of the free acids of the formula entsprechen, in dercorrespond in the X Wasserstoff, Chlor, Brom, Cyan, Nitro, C1- bis C^-Alkyl, C -Cu-Alkylmercapto, Alkylsulfonyl, Alkylsulfinyl, Alkanoyl, Benzoyl, Carboxyl, C1-C4-AIkOXy, Di-C^C^-Alkylamino, NHCO-C,- bis C^-Alkyl, Hydroxysulfonyl oder gegebenenfalls substituiertes Carbamoyl oder Sulfamoyl,X hydrogen, chlorine, bromine, cyano, nitro, C 1 - to C ^ -alkyl, C -Cu-alkylmercapto, alkylsulfonyl, alkylsulfinyl, alkanoyl, benzoyl, carboxyl, C 1 -C 4 -AIkOXy, di-C ^ C ^ -Alkylamino, NHCO-C, - to C ^ -alkyl, hydroxysulfonyl or optionally substituted carbamoyl or sulfamoyl, E einen Rest der FormelnE is a remainder of the formulas HO,SHO, S HO,S NH HO, S NH • (HO5S)111 • (HO 5 S) 111 (SO5H)n '(SO 5 H) n ' H5C CH, HIfX^ H 5 C CH, HIfX ^ oderor r'r ' 80984 2/018980984 2/0189 ORIGINAL INSPECTEDORIGINAL INSPECTED j 21 I 6033 j 21 I 6033 R Wasserstoff, Methyl, Methoxy oder Athoxy,R is hydrogen, methyl, methoxy or ethoxy, 2 R Wasserstoff, Chlor, Methyl, Äthyl, Benzyl, Sulfobenzyl, Methoxy,2 R hydrogen, chlorine, methyl, ethyl, benzyl, sulfobenzyl, methoxy, Äthoxy, NHCO-C1- bis C.-Alkyl, NHCOCH2Cl, NHCOCHCl , NHCONH2 3Ethoxy, NHCO-C 1 - to C.-alkyl, NHCOCH 2 Cl, NHCOCHCl, NHCONH 2 3 oder SO H, Wasserstoff, C1- bis C.-Alkyl, C9- oder C,-Hydroxy- oder Di-or SO H, hydrogen, C 1 - to C-alkyl, C 9 - or C, -hydroxy- or di- ß-SuIfoäthylf - y hydroxyalkyl, γ-Sulfopropyl, ß-Cyanäthyl, ß-Hydroxy-y-chlorpropyl, C- bis C -Alkoxyäthyl, Acetoxyäthyl, ß-Chloräthyl, γ-Amino- oder -Acetylaminopropyl, ß-Carboxyläthyl, ß-Carbamoyläthyl, Benzyl, Sulfobenzyl, Phenyläthyl, Sulfophenyläthyl oder Cyclohexyl,ß-SuIfoäthylf - y hydroxyalkyl, γ- sulfopropyl, ß-cyanoethyl, ß-hydroxy-y-chloropropyl, C- to C -alkoxyethyl, acetoxyethyl, ß-chloroethyl, γ-amino- or -acetylaminopropyl, ß-carboxylethyl, ß- Carbamoylethyl, benzyl, sulfobenzyl, phenylethyl, sulfophenylethyl or cyclohexyl, R^ C -bis C -Alkyl, C- oder C,-Hydroxyalkyl, ß-Cyanäthyl, ß-Chlor-R ^ C -to C -alkyl, C- or C, -hydroxyalkyl, ß-cyanoethyl, ß-chlorine 14 214 2 äthyl, C.- bis C .-Alkoxyäthyl, Benzyl oder Sulfobenzyl,ethyl, C.- to C.-alkoxyethyl, benzyl or sulfobenzyl, 5 R Amino, Acetylamino, Chloracetylamino, Phenoxyacetylamino, Benzoylamino, Chlorbenzoylamino oder Dichlorbenzoylamino,5 R amino, acetylamino, chloroacetylamino, phenoxyacetylamino, Benzoylamino, chlorobenzoylamino or dichlorobenzoylamino, R Methyl, Chlormethyl, Phenyl, Chlorphenyl oder Acetylamino,R methyl, chloromethyl, phenyl, chlorophenyl or acetylamino, 7 R1 C- bis Cg-Alkyl, C2- oder C,-Hydroxyalkyl, Phenyl-C,- bis7 R 1 C- to Cg-alkyl, C 2 - or C, -hydroxyalkyl, phenyl-C, - bis C -Alkyl, Cyclohexyl oder Phenyl, m die Zahlen 0, 1 oder 2 und η die Zahlen 1 oder 2 bedeuten.C1-4 alkyl, cyclohexyl or phenyl, m denotes the numbers 0, 1 or 2 and η denotes the numbers 1 or 2. 2. Farbstoffe gemäß Anspruch 1 der Formel2. Dyestuffs according to Claim 1 of the formula N=N-KN = N-K 809842/0189809842/0189 o.z. 32o.z. 32 271ÖÜ33271ÖÜ33 in der X Wasserstoff, Chlor oder Brom und K einen Rest der Formel ^^ ιin which X is hydrogen, chlorine or bromine and K is a radical of the formula ^^ ι -R-R R^ NHR ^ NH υ \i-u oder ι- ι υ \ iu or ι- ι '2 V'2 V bedeuten.mean. 3. Verfahren zur Herstellung von Farbstoffen gemäß Anspruch 1, dadurch gekennzeichnet, daß man eine Diazoverbindung von Aminen der Formel 3. A process for the preparation of dyestuffs according to claim 1, characterized in that a diazo compound of amines of the formula χ SO3H χ SO 3 H NH2 NH 2 mit einer Kupplungskomponente der Formel HK with a coupling component of the formula HK umsetzt,implements, X und K haben dabei die für Anspruch 1 angegebenen Bedeutungen.X and K have the meanings given for claim 1. 4. Farbstoffzubereitungen für das Färben von natürlichen und syn thetischen Polyamiden sowie Pelz enthaltend neben üblichen Bestandteilen einen Farbstoff gemäß Anspruch 4. Dyestuff preparations for dyeing natural and syn thetic polyamides and fur containing, in addition to the usual ingredients, a dye according to claim 809842/0189809842/0189
DE19772716033 1977-04-09 1977-04-09 ACID AZO DYES Pending DE2716033A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DE19772716033 DE2716033A1 (en) 1977-04-09 1977-04-09 ACID AZO DYES
IT21636/78A IT1095370B (en) 1977-04-09 1978-03-24 ACID AZO DYES
FR7809681A FR2386585A1 (en) 1977-04-09 1978-03-31 Acid azo dyes contg. amino-benzothiazole sulphonic acid gps. - for natural and synthetic polyamide(s), pelts, leather etc.
JP4134378A JPS53126034A (en) 1977-04-09 1978-04-10 Acid azo dye

Applications Claiming Priority (1)

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DE (1) DE2716033A1 (en)
FR (1) FR2386585A1 (en)
IT (1) IT1095370B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5532342A (en) * 1992-06-02 1996-07-02 Mitsubishi Chemical Corporation Azo metal chelate compound
US5691458A (en) * 1996-09-18 1997-11-25 Polaroid Corporation Benzoisothiazole azo dyes
WO2025070630A1 (en) * 2023-09-29 2025-04-03 富士フイルム株式会社 Composition, light absorption filter, optical filter and manufacturing method therefor, organic electroluminescent display device, inorganic electroluminescent display device, liquid crystal display device, and compound

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4255326A (en) * 1979-03-30 1981-03-10 Eastman Kodak Company Nitrogen and/or sulfur containing heterocyclic azo dyes with aniline, tetrahydroquinoline and benzomorpholine couplers having sulfate group
JPS58104956A (en) * 1981-12-18 1983-06-22 Sumitomo Chem Co Ltd Preparation of azo dye
CN111849194B (en) * 2020-07-27 2021-09-17 浙江青松轻纺股份有限公司 Benzisothiazole dye monomer compound, preparation method and application in hydrophobic fiber material dyeing
WO2024111572A1 (en) * 2022-11-25 2024-05-30 富士フイルム株式会社 Coloring composition, method for producing colored article, colored article, and kit

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5532342A (en) * 1992-06-02 1996-07-02 Mitsubishi Chemical Corporation Azo metal chelate compound
US5691458A (en) * 1996-09-18 1997-11-25 Polaroid Corporation Benzoisothiazole azo dyes
WO2025070630A1 (en) * 2023-09-29 2025-04-03 富士フイルム株式会社 Composition, light absorption filter, optical filter and manufacturing method therefor, organic electroluminescent display device, inorganic electroluminescent display device, liquid crystal display device, and compound

Also Published As

Publication number Publication date
IT1095370B (en) 1985-08-10
IT7821636A0 (en) 1978-03-24
JPS53126034A (en) 1978-11-02
FR2386585A1 (en) 1978-11-03

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