DE2120095A1 - Water-insoluble monoazo dyes and process for their preparation - Google Patents

Description

Be ?. '. 29o8 CASSELLA FARBWERKE MAINKUR

SHARED COMPANY

FRANKFURT (MAIN) -FECHENHEIm 6 Frankfurt (Main) -FechenheiTn,

April 2, 1971

Dr. Eu / Th

Water-insoluble monoazo dyes and methods for their Manufacturing

The present invention relates to valuable new, water-insoluble Monoazo dyes of the general formula

in the] L, an aromatic which is free of water-solubilizing groups rest

Rp is a -0-CO- or -CO-0- group

R, an aromatic which is free of water-solubilizing groups rest

X is hydrogen, cyano, alkoxy, carboxy, optionally branched and / or substituted alkyl, optionally branched and / or substituted AlkWyl, optionally substituted cycloalkyl, Aralkyl, aryl or a heterocyclic radical

Y is hydrogen, one cyano, one optionally branched

209845 / 11-51

- 2 - - Ref. 29o8

and / or substituted alkyl, optionally branched and / or substituted alkenyl, optionally substituted cycloalkyl, aralkyl, aryl group or the radicals / 6

-GOOR-, -GOR ₅ , -QO-M , -SO ₂ R ₅ or

/ β ^R 7

SOp-H \ t where R. and R, - an alkyl group, R ₅ further

also an optionally substituted cycloalkyl, aralkyl or aryl group and Rg and R _{7 are} hydrogen, an alkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, aralkyl or aryl group, the alkyl radical βRg and R ₇ also being connected directly or via a heteroatom Z can denote hydrogen, an optionally substituted amino, optionally branched and / or substituted alkyl, optionally branched and / or substituted alkenyl, optionally substituted cycloalkyl, aralkyl or aryl group or a heterocyclic radical.

The radical R- is, for example, a phenyl or llaphthyl radical. The radical R is, for example, a phenylene or naphthylene radical. As substituents for the radicals R-, and R, and for aryl groups in the radicals X, Y and Z come, for example, one or more halogen atoms, Cyano, alkyl or alkoxy groups are suitable. In the radicals X, Y and Z, the alkyl or alkenyl groups can, for example

2 Ü 9 R 4 5/1 1 5 1

- 3 - Ref. 29o €

be substituted by an oyan, hydroxy, acyloxy, alkoxy, aryloxy or an alkyl or arylaraino-caribonyloxy group. Furthermore also by a mono- or dialkyltemino group, whereby the alkyl groups can also be connected directly or via a heteroatom. An amino group in the Z position can be mono- or disubstituted by alkyl groups or acylated by an aliphatic or aromatic acid radical. The chain length of the alkyl or alkenyl groups in the radicals X, Y and Z is preferably 1 to 6 carbon atoms. An X or Z-position, heterocyclic radical can be, for example, a pyridyl, thiazolyl, benzothiazolyl, imidazolyl, benzimidazolyl, thienyl, furyl or a Pyrrolpl ^r-TG fhrp.ppe. The new dyes can be obtained by using an amine of the general formula

R ₁ -R ₂ -R ₅ -KH ₂ II

which is free of water-solubilizing groups, diazotized and with a 6 $ hydroxy-2-pyridone derivative of the general formula

couples, where R ₁ , R ₂ , R *, X, Y and Z have the meaning given above.

With regard to the formation of the disperse dyes, it can be advantageous to use a mixture of two or more amines of the to diazotize general formula II and either with a 6-hydroxy-2-pyridone derivative of the general formula III or a To couple a mixture of two or more compounds of the general formula III.

2 0 9 8 4 5/1151

- 4 - Ref. 29o8

212GGOb

A mixture of dyes of the general formula I can also be prepared in that an amine of the general formula II is diazotized and coupled with a mixture of two or more compounds of the general formula III. It is possible that the dyes according to the invention of the general formula I and the starting compounds of the general Formula III exist in tautomeric forms. For example, the following tautomeric forms for the dyes are general Formula I and the starting compounds III are conceivable:

ο cr ^ - ir *** ο

ζ ζ

X ^Ia

OH

Ib Z

ό 'y ^ o

Z III a

/ T

0 I OH

III b

0 9 8 4 5/1151

- '5 - - Ref. 29o8

In the event that Z = H, the following also apply, for example tautomeric forms .possible

HO ^ N ^ OH

Ic III c

In the context of the present invention, among the inventive Dyes I and the starting compounds III also understood the possible tautomers.

The amines of the general formula II required as starting materials are preferably prepared by first a nitroarylcarboxylic acid chloride IV with a hydroxyaryl compound Y or a nitro-hydroxy-aryl compound VII with a Arylcarboxylic acid chloride YIII urageetitit and the resulting Hltroester VI a or VI b, for example by hydrogenation in a known manner Way reduced to the corresponding amines II a and II b:

R ₁ -OH + Cl-CO-R ₃ -HO ₂ - R ₁ -O-CO-R ₅ -NO ₂ - R ₁ -O-CO-R ₅ -NH ₂ V IV VI a II a

20 98 45/1151

- 6 -. Ref. 29o8

21200S5

R ₁ -CO-OR ₃ -NO ₂ - R ₁ -CO-OR ₃ -NH ₂

VIII VII VI b II b

The nitro-arylcarboxylic acid chlorides of the general formula IV can be prepared from the associated nitro-arylcarboxylic acids by suitable methods that are necessary for the transfer of a Carboxylic acid in the acid chloride are known.

Examples of nitro-arylcarboxylic acids that can be used are:

2-, 3- or 4-nitrobenzoic acid, 2-nitro-3- or 4-methyl-benzoic acid, 2-nitro-5-methoiy-benzoic acid, 2-nitro-3- »4- or 5-chloro-benzoic acid, 2-Hitro-3-chloro-6-methoxy-benzoic acid, 2-Hitro-3,5-dichloro-benzoic acid, 2-nitro-3,4 or. 5-chloro-benzoic acid, 2-nitro-4-bromo-6-methyl-benzoic acid, 2-nitro-3,5-dibromo-benzoic acid, 3-Hitro-4 or. 6-methyl-benzoic acid, 3-nitro-4- or 6-metho3Cy-benzoic acid, 3-lfitro-4- or 6-ethoxy-benzoic acid, 3-nitro-2-, 4- »5- or 6-chloro-benzoic acid,

2 0 9 8 4 5/1151

- 7 - Ref. 29o8

3-nitro-2-chloro-4 ■ -πlβthyl-benzoic acid, 3-nitro-4-chloro-2- or 6-ynethyl-benzoic acid, 3-nitro-2-, 4-, 5- or 6-bromobenzoic acid, 3-nitro-4-bpöm-2- or 6-methylbenzoic acid, 4-nitro-2- or 3-methyl-benzoic acid, 4-nitro-3-methoxy- or ethoxy-benzoic acid, 4-nitro-2- or 3-chlorobenzoic acid, 4-nitro-2- or. 3-bromo-benzoic acid, 4-1! 1 ^ 0-3JS-CIiClIlOr- or dibrotn-benzoic acid, 4-, 5- or 8-nitro-l-naphthoic acid, S-chloro-e-nitro-l-naphthoic acid, S-bromo-e-nitro-l-naphthoic acid, 1-, 4-, 5- or. 8-Hitro-2-napb.thoic acid, l-nitro-6-methyl-2-naplitlioesäure or the 4-nitro-l-methyl-2-naplltlloesäuΓβ.

As nitro-hydroxy-aryl compounds of the general formula VII can be used, for example:

2-, 3- or 4-nitro-flhenol, 2-nitro-3-, 4-, 5- or 6-methylphenol, 3- * tirrn -? -, 4- _f 5r- or 6-methyl -phenol,

2 0 S 8 AB / 1 1 5 1

- 8 - Ref. 29o8

4-nitro-2 or. 3-methyl-phenol,

2-nitro-3,5-, 3,6-, 4,5- or 4 »6-dimethyl-phenol, 3-nitro-2,5-, 2,6-, 4,6- or 5, 6-dimethyl-phenol, 4-nitro-2,5-, 2.6 _T or 3,5-dimethyl-phenol, 2-nitro-3-meth.yl-5- or 6-methoxyplaenol, 2 -ITitro-4-Tetliyl-6-iDetlioxy-phenol, 2-Hitro-5-met] iyl-6-tnet] ioxy-plienol, 3-nitro-4-Tetliyl-6-inet] ioxyphenol, 3- Liitro-2-methoxy-4-methyl-plienol, 3-nitro-2-methoxy-6-methyl-methyl-plienol, 4-nitro-2-methoxy-3-roethyl-phenol, 4-5ii; ro-2-methoxy -5-ethylphenol, 4-5ilro-3-inethoxy-5-diethylphenol, 3- »4-, 5- or e-nitro-pyrocate-1-methyl ether, 4-nitro-resorcinol-1 -respectively. 3-methyl ether, 5-nitro-resorcinol-1-ynethyl ether,

2-rnitro-hydroquinone-1 or 2-methyl oil, 24B [itro-3-, 4-i5- or. 6-chloro- or bromophenol, 2-nitro-, 3,4-i3,5-j3,6- or. 4,6-dichloro- or dibromophenol, 2-Ni tro-6-chloro-4-broiD-phenol,

2-nitro-5-chloro- or bromo-ö-methyl-phenol, 2-lϊitΓO-4-methyl-6-chloro- or brota-phenol, 2-Hitro-4-bromo-6-ynethyl-phenol,

3-nitro-2-, 4-, 5- or 6-chloro- or -brotn-phenol, 3-nitro-4,6-dichloro-phenol,

2 0 9 8 4 5/1151

- 9 - Ref. 29o8

3-nitro-2-methyl-6-chlorophenol, 3-nitro-2-chloro-6-niet] iyl-phenol, 4-ITitro-2-chloro- or bromophenol, 4-nitro-2, 6-dichloro- or dibromophenol, 4-nitro-2-chloro-6-bromo-ph.enol, 4-nitro-5-chloro-6-methyl-phenol, 2-, 4- or 5 -Nitro-1-naphthol, 2-nitro-4-bromo-1-naphthol, 1 ^, 6- or 8-nitro-2-naphthol, _v .

l-nitro-6-bromo-2-naphthol or l-nitro-o-methyl ^ -naphthol "

The aryl carboxylic acid chlorides of the general formula VIII can from the associated aryl carboxylic acids suitable methods can be prepared for the transfer of a carboxylic acid in which acid chloride are known.

The following can be used as aryl carboxylic acids, for example:

2-, 3- or 4-methyl- or ethyl-benzoic acid, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dimethylbenzoic acid, 2-, 3- or 4-methoxy- or ethoxy-benzoic acid, 2-methyl-4-, 5- or 6-methoxy-benzoic acid, 3-methyl-2-, 4-, 5- or 6-methoxy-benzoic acid, 4-methyl-2- or 3-methoxy-benzoic acid, 2,3-, 2,4-, 2,5-, 2,6-, 3f4- or 3,5-dimethoxybenzoic acid,

20984R / 1151

- Io ι Ref. 29o8

2120035

2-, 3- or 4-chloro- or bromo- or cyano-benzoic acid, 2,3-, 2,4-, 2,5-, 2,6-, 314-3, 5-dichloro- or Dibrorobenzoic acid, 2-methyl-3-, 4- or 5-chlorobenzoic acid, 3-methyl-4-, 5- or 6-chlorobenzoic acid, 4-methyl-2- or. 3-chloro-benzoic acid, 2-methoxy-3- or 4-chloro-benzoic acid, 3-methoxy-2-, 4- or 6-chloro-benzoic acid, 4-methoxy-2-or. 3-chloro-benzoic acid, 2-methyl-5-bromo-benzoic acid, 3-methyl-4- or 6-bromo-benzoic acid, 4-methyl-2- or 3-bromo-benzoic acid, 1- or 2- Haphthoic acid, 2-, 4- »6- or 8-methyl-i-naphthoic acid, 4-ethyl-1-naphthoic acid, 4-isopropyl-1-naphthoic acid, 2,6- or 2,7-dimethyl-1- naphthoic acid, 2-, 3- »4 ~, 5-, 6-, 7- or 8-methoxy-1-naphthoic acid, 4-, 5- or 8-oleo-1-naphthoic acid, 4-, 5- or 8-Broin-1-naphthoic acid, 5,8-dichloro-1-naphthoic acid, 1-, 3- and 6-methyl-2-naphthoic acid, 4,6-dimethyl-2-naphthoic acid, 1-, 3- »4 - * 5-, 6-, 7- or 8-methoxy-2-naphthoic acid, 1- or 5-bromo-2-naphthoic acid or 4,5- or ^, S-dichloro ^ -naphthoic acid.

1-, 3- »5- or S-chloro - ^ - naphthoic acid.

098 4 5 / 115t

-U- R3f, 29o8

2120095 As hydroxy-aryl compounds of the general formula V can be used, for example:

Phenol,

2-, 3- or 4-methylphenol, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dimethylphenol, 2-, 3- or 4-methoxy-phenol, 2-methoxy-3-, 4-, 5- or 6-methyl-phenol, 3-methoxy-5- or. 6-methyl-phenol, 4-methoxy-5- or 6-methyl-phenol, 2,3-, 2,4- or 3,5-dimethoxyphenol, 2-, 3- or 4-chloro or bromo- or cyano-phenol, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dichloro- or dibromophenol, 2- Methyl-3-, 4-, 5- or 6-chloro- or bromophenol, 3-methyl-2-, 4- or 6-chloro- or bromophenol, 4-methyl-5- or 6-chloro- or bromophenol, 4- or 5-chloro- or bromopychol-1-methyl ether, 4-chloro- or bromoresorcinol-1 or 3-methyl ether, 5-chloro -resorcinol-1-methyl ether, 2-chloro-hydroquinone-1 or 2-methyl ether,

1- or 2-naphthol,

2-, 3-, 4- or 7-methyl-l-naphthol, 2-ethyl-l-naphthol,

2- or 4-isopropyl-1-naphthol

ORIQINAt

209845/1151

- 12 - Ref. <° 9o8

2 1 2 Ü U

3,6-, 3,7-, 4,6-, 4,7- or 6,7-dimethyl-1-naphthol, 4-, 5-, 6-, 7- or 8-methoxy-l-naphthol, 4-ethoxy-1-naphthol,

2-, 3-, 4-, 5-, 5-, 7- or 8-chloro-l-naphthol, 2,3-, 2,4-, 5,7-, 5,8-dichloro-1-naphthol, 2-chloro-4-bromo-l-naphthol, 2-, 3-, 4-, 5-, 6-, 7- or 8-bromo-l-naphthol, 2-ethyl-4-bromo-1-naphthol, 2,4-dibroin-1-naphthol,

1- or 6-methyl-2-naphthol, l-ethyl-2-naphthol,

3-isopropyl-2-naphthol,

1,4-, 3,6-, 3 ', 7- or 6,7-dimethyl-2-naphthol, 1-, 3-, 6- or 7-methoxy-2-naphthol, 6-ethoxy-2-naphthol,

1-, 3-, 4-, 5-, 6-, 7- or 8-chloro-2-naphthol, 1-methyl-4-chloro-2-naphthol, 1,3- or 1,4-dichloro-2-naphthol, 1-, 3-, 4-, 5-, 6-, 7- or 8-bromo-2-naphthol, l-methyl-6-bromo-2-naphthol, 1-ethyl-6-bromo-2-naphthol or 1,6-, 3,6-3,7- or 4,6-dibromo-2-naphthol.

OfBGtNAL INSPECTED

209845/1151

- 13 - set. .2.908

212Ü095

As coupling components of the general formula III, for example, those 6-hydroxy-2-pyridone derivatives are suitable which, in the Z position, are hydrogen or a methyl, ethyl, iBr or iso-propyl, ethylene, a.Methyl-aethylene , n- _f iso- or sec-butyl-, η- or iso-amyl-, n-hexyl-, 2-dimethylamino or diethylamino-ethyl, 2-oyan-ethyl, 2-hydroxy ethyl, 2-acetoxy-ethyl, 2-phenoxy-acetoxy-ethyl, 1-methyl-2-hydroxy-ethyl, 3-hydroxy-propyl, 2-phenoxy-ethyl, 3-methoxy-propyl, cyclohexyl -, benzyl, 3-methylbenzyl, phenyl, 2- or 4-methyl-phenyl-, 2,4-dimethylphenyl-, 2-chloro-4-methyl-phenyl-, 2- or 4-chloro phenyl-, 2- or 4-methoxyphenyl-, 2,5-dimethyl-4-chlorophenyl-, 2-, 3- or 4-carbethoxyphenyl-, 2-, 3- or 4- Acetyl-phenyl-, 2-, 3- or 4-benzoyl-phenyl-, 2-, 3- or 4-dimethyl-carbamylphenyl-, 2-, 3- or 4-diethyl-carbamyl-phenyl-, 2 -, 3- or 4-iso-propyl-carbamyl-phenyl-, 2-, 3- or 4-methyl-sulfonylphenyl-, 2-, 3- or 4-phenyl-sulfonyl-phenyl-, 2-, 3- or 4-dimethyl-sulfamyl-phen yl-, 2-, 3- or 4-iso-propyl-sulfamyl-phenyl-, 2-ethyl- or 2-phenyl-carbonyloxy-ethyl-, amino-, mono-methylamino-, acetyl-methylamino-, benzoylmethylamino - Or contain dimethyl-amino groups.

20984 5/1151

- 14 - · ran. 29οβ

2! 2OQT. ^ i

Also suitable are compounds of the general formula III which, in the X position, are, for example, hydrogen or a cyano, ethoxy, carboxyethyl, methyl, ethyl,
2-hydroxy-ethyl-, 2-cyano-ethyl-2-acetoxy-ethyl-, 2-benzoyl-exyaethyl-, 2-methoxy-ethyl-, 2-phenoxy-ethyl-, 2-ethylamino- and 2-phenylamino -carbonyloxy-ethyl-, 2-monomethylamino- or 2-dimethylamino-ethyl-, ethylene-, α, methylethylene, n- or iso-propyl-, n-, iso- or sec. butyl-, η- or iso-amyl, n-hexyl, cycloalkyl, benzyl, phenyl, 4'-methylphenyl-G group or the radical -CH ₂ -COOCH-Z.
The compounds of the general formula III can, for example, in the Y-position hydrogen, a cyano, methyl, ethyl,. 2-diaethylamino-ethyl-, n- or iso-propyl-, ethylene,
a.Methy1-ethylene, n-, iso- or sec-butyl, η- or iso-amyl, n-hexyl, cycloalkyl, benzyl or aryl group or contain the following radicals:
Methyl carboxylate,
Carboxylic acid ethyl ester,
Carboxylic acid n- or iso-propyl ester,
Carboxylic acid n-, iso- or see. butyl ester,
Carboxylic acid n- or iso-amyl ester,
Carboxylic acid-n-hexyl ^ ater,
Acetyl,

ORiGINAt INSPECTED

2Ό9845 / 1151

- 15 - At. ? .9ο8

Propionyl, capronyl,

Caprylic,

Hexahydrolienzoyl, Phenacetyl, Benzoyl,

4-methylbenzoyl, 2,4-dimethyl-benzoyl, 4-methoxy-benzoyl, 4-chloro-benzoyl, Carboxamide, carboxylic acid mono-methylamide, Carboxylic acid dimethylamide, carboxylic acid ethylenimide, Carboxylic acid monoethylamide, Carbonic acid mono-iso-propylamide, Carboxylic acid diethylamide, Carboxylic acid mono-oxaethylamide, Carboxylic acid-inono-y-thiiethoxy-propylaniid Carboxylic acid morpholide, carboxylic acid piperidide, Carboxylic acid cyclohexylamide, carboxylic acid benzylamide,

9845/1151

- 16 - Ref. 29o3

Carboxylic acid anilide, carboxylic acid (4-yneth.yl anilide ^ carboxylic acid (H-methyl anilide), methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso- or, respectively, see-butylsulfonyl, n - or iso-amylsulfonyl, n-hexylsulfonyl, benzylsulfonyl, phenylsulfonyl, 4-methyl-phenyl-sulfonyl, 2,4-dimethyl-phenyl-sulfonyl, 4 - methoxyphenyl-sulfonyl, 4-chlorophenyl sulfonyl, sulfonic acid amide, sulfonic acid monomethylamide, sulfonic acid dimethylamide, sulfonic acid aethylenitnide, sulfonic acid monoethylaTnide, sulfonic acid mono-iso-propylamide, sulfonic acid diethylamide, sulfonic acid mono-oxethylamide,

OfKGINAL INSPECTED 0 9 8 4 5/1151

- 17 - Kef. 29 <8

Sulfonic acid-mono-y-methoxy-propylamide, sulfonic acid-morpholide,
Sulfonic acid piperidide,
SuIf ons aure-cyclohexyiaiSi.d,
Sulfonic acid benzylamide,
Sulfonic acid anilide,
Sulfonic acid (4-methyl-anilide),
Sulfonic acid (N-methyl-anilide).

Of course, suitable starting compounds are the general formula III also those 6-hydroxy-2-pyridone derivatives, those in the X, T or Z position di * »or Ui substituted are, in particular also the above for the X, Y and Z-position listed substituents into consideration come.

The preparation of the coupling components of the general formula III can be carried out in analogy to the synthesis of Guareschi, Reports of the German Chemical Society £ 9, (1897), Heferate, page 654- f, by condensation of appropriately substituted acetic acid amides or hydrazides with appropriately substituted β-ketocarboxylic acid esters or by various methods as described, for example, in the monograph "Pyridine an its Derivatives Part. 3 ^H" by Erwin Klingsberg.

209845/1151

- 18 - Ref. 29o3

This monograph is part of the Arnold Weissberger published series "The Chemistry of Heterocyclie Componends" published by Interscience Publishers.

The dyes according to the invention are particularly suitable for dyeing and printing structures made of synthetic materials, such as polyolefins, polyvinyl compounds, polyamide, polyacrylamide, cellulose 2l / 2-acetate, Cellulose triacetate and especially polyester materials such as polyethylene glycol terephthalate. You then deliver the usual dyeing and printing processes, yellow to orange dyeings and prints with very good fastness properties, especially very good fastness to flour and sublimation.

The dyeing of said fiber material with the inventive Dyes are expediently made from an aqueous suspension in Presence of orers between about 80 - llo ° C, in their absence of carriers between about llo - 14o ° C as well as after so-called thermal fixing process at around 180 - 23o ° C. The new dyes are particularly suitable for dyeing using the carrier process.

209845/1151

- 19 - Ref. 29o8

Printing on the materials mentioned can be carried out in such a way that the goods printed with the new dyes are in Presence of a carrier at temperatures between about 80-100 ° C. or in the absence of a carrier at about Ho - 14o ° C steamed or according to the so-called thermosetting process is treated at around 180 - 23o ° C. The dyes of the invention are also useful for coloring polystyrene suitable.

A preferred group of dyes according to the invention are those in which in the general formula IR _{1 is} a phenyl radical

R _{2 is} -0-CO- or -CO-O-

R, an o-, m- or p-phenylene radical

X is a methyl or ethyl group

Y is a cyano group

Z denotes hydrogen, a methyl or ethyl group, where the phenyl radical R ₁ and / or the phenylene radical R can also be substituted one or more times by methyl, ethyl, methoxy, ethaxy , halogen.

Example 1:

a) 21.3 parts by weight of 3-amino-benzoic acid phenyl ester are in Parts by weight of water with the addition of 72 parts by weight of 3o $ iger Hydrochloric acid dissolved by briefly heating to 60 ° C,

209845/1151

- 2ο - Ref. 29o8

Compartment, cooling, sodium nitrite in 5o wt. Parts of diazotized at 0 to + 5 ⁰ C with a solution of 7.7 wt. Parts of water. The filtered, clear diazo solution is then left in a suspension of 16.5 parts by weight of STGyD ^ e ^ ffl ^ thylfiS ^ esiy ^ aylypydori in 400 parts by weight of water, 16.6 parts by weight of sodium hydroxide solution 33 ° Be "and 41.0 parts by weight of sodium acetate flow in and keep the reaction temperature during the coupling by adding 500 parts by weight of ice at 0 to + 5 ° C. The resulting dye is filtered off with suction, washed neutral with water and dried is a yellow powder that dissolves in concentrated sulfuric acid with a reddish yellow color.

b) 1.0 parts by weight of the finely dispersed dye thus obtained the formula

H
are stirred into 2,000 parts by weight of water. The pH is adjusted to 5-6 with acetic acid, and 4 parts by weight of ammonium sulfate and 2 parts by weight of a commercially available dispersant based on a naphthalenesulfonic acid-formaldehyde condensate are added.

2 0 9 8 4 5/1151

- 21 - Ref. 29o8

100 parts by weight are added to the dye liquor thus obtained a polyester fabric based on polyethylene glycol terephthalate and stains for 1 l / 2 hours at 12o - 13o ° G, after, subsequent rinsing, reductive aftertreatment with an o, 2% alkaline nfttrium dithionite solution for 15 minutes at 60 ° -70 ° C., rinsing and drying, a yellow dyeing with very good fastness properties, in particular very good lightfastness, is obtained.

In the table below are further inventions Dyestuffs indicated which dye or print on polyester materials with likewise very good fastness properties deliver.

Table 1

209845/1 151

a «a.

Ref. 29o8

212U095

GH,

GH,

CH,

GH

CH

OH ₃

-0-0-

Il

O -0-0-

Il

O -0-0-

Il

O -0-0-

Il

-0-0-

Il

-0-0-

Il O

-0-0-

Il O

-0-0-

Il O

-0-0-Il O

-0-0-

Il O

-0-0-

Il

-GH, ¹ GN -H

-GN. -H

-O-

-GH, -GN -H

-CH, -GN '-H

-CH, -GN -H

-CH, -GN -H

-GN -H

■ b

-CH, -CN -H

-CH, -GN -H

-CH, -CN I -H

-GH ₃ -CN

-H

20984 5/1151

■ 2120035

Ref. 29o8

No.

R ₂ R ₅ XY

OCH

12th

13th

14th

15th

16.

17th

18th

19. H, C0- ('

2ο.

OCH,

OCH,

OCH,

OCH

OCH,

21.

22nd

23

H ₅ CO

Cl

Cl

-0-0-

-0-0-

-0-0-

-0-0-

-0-0-

-0-C-

-0-0-

-0-0-

0 -0-0-

-0-0-

-0-0-

-0-0-

-O

-CH * -CN

-CN

-CH, -CN

-Qs- - ^GH 3

-0

-CH, -CN

-CH, -CN

-CH, -CN

-CH ₅ -CN

-CH, -CN

-CH, -CN

-CN -H

-CN -H

-CN -H

5/1151

Ref. 29p8

No. R _n

Cl

Eq

Gl-

Eq

CH,

-o-c-

Il ο

-o-o-

Il ο

-o-o-

Il ο

-0-C-

Il O

-0-0-

Il O

-o-c-

Il

-0-0-

Il Q

-C-O-

Ii ι:

O O

-C-O-

Il I!

O O

-G-O-

Il

-C-O-II O

-GH, -GN

-CH, -GN

-GH, -GN

-O

-GH, -CN

-CH,

<y

-CH, -CN

-H

-H

-H

-CH, -CN -H

-CH, -CN -H

-GH, -GN -H

-CH, -CN -H

-H

-GH -H

-GN -H

-H

209845/1151

Ref. 29o8

No.

35.

36.

37.

38.

39.

4o.

41.

42.

43.

44.

45.

/ ^H 3 I.

CH

!

-C-O-

Il O

CH

CH,

CH

^Η 3 ^σ Λ_

-C-O-

Il 0

-C-O-

Il ο

-CO- II 0

-C-O-

Il 0

-C-O-

Il ο

-CH ₃ -CN

-O

-CH 3 -CH 3 -CH -CH 3;

-CH

O-i

3 -CN -GH ₃ -CN -CH ₃ -CN
I.

-H

-CH ₃ -CN -H

-CN ^; -H

-CN -H

-CN -H

-CN -H

-CN i -H

-CH, I -GN; -H

-H

-H

-TT

209845/1151

Ref. 29o8

Ho

OCH,

46th! "

47.

48.

OCH

OCH,

5ο.

H, 0

51. I.

52.

53-

54.

55.

56.

Cl

Cl

Cl

Cl

Cl

-G-O-

Il O

-C-O-

Il O

-C-O-

I! ο

-C-O-

Il ο

-C-O-

Ii ο.

-G-O-

-C-O-

Il ο

-C-O-

Il ο

-C-O-

O -G-O-

Il ο

-G-O-

Ii

■ ά

-CH, -CH -CH, -CH -CH, -CH

; -CH ₃

-CH

-CH, -CH

-CH, -CH

-CH, -CH -CH, -CH -CH, ' -CH -CH, ■ -CH

-H

-H

-H

-H

209845/1151

Ref. 29o8

No. H,

Cl

-O

-CO- II 0

-C-O-

Il 0

-C-O-

Il

0 -C-O-

Il

-o-c-Il 0

-o-c-Il 0

-0-0-

Il

-o-c-

Il

-o-c-

Il

-o-c-

Il

0 -0-0-

Il

-CN -H

-CH ₃ -CN -H -CH ₃ -CN -H -CH, -CN -H CH ₃ " ^GH 3 -CN -H CH ~ ^CH 3 ■ -CN -H

-CH, -CN

CH,

-CH _W -CN

-CH, -CN

CH

-CH, I -CN

J I

CH

-CN -H

-H

-H

-H

2098A5 / 1151

Hot. ^ yob

No. R-, R,

68.

69. β

71. Η, (

72.

73.

74.

H ₃ C

75.

76.

Cl

77.

-0-0-

0. -O-C-

-0-0-

-0-C-

-0-C-

O -0-C-

-0-0-Il O

-o-c-

-o-c-

-0-0-

OH

OCH-

OCH,

OCH,

OCH,

CN

-CH, -CN

-H

-CN -H

-CN -H

-CN -H

-CH -H

- [- CH, -CN -H

-CH, -CN -H

-CH, -CN I -H

-CH, -CN i -H '

-H

209845/1151

Ref. 29o8

No. R-,

R.

78. ! η c- "\ 7 ~ -0-0-
Il 1
j Il
0 79. j
JH ₃ C ( V = / -0-0-
Il
0 8ο. 'Cl- -0-0-
Il 81. j
1 ο Il
F 0
-0-0-
Il
0

-CH ₃

'-0H-,

Cl

89

Cl

H,

CH,

o-o-

Il ο

o-o-

Il

o-c-

Il ο

o-c-

Il ο

o-o-

Il ο

oo-Il O

0-0-

Il

O -0-0-

Il

Cl

i Cl

:-Oh.

-CH,

·· ei

C ₀ H.

209

CH

OCH

-CH,

-CH,

! -GH,

-CH,

8 4 5/1151

-ON

-CN

-CN

-H ;

-H

-H

-CN! -H

-cn: '-H

-CN

-CN

-ON

-CN

-GN

-GN

-CN

-H

-H

-H

-GH,

-H

-H

- 5ο

Ref. 29o8

Oi

ο-

€>

C-O-

(I 0

C-O-

Il 0

-G-O-

Il

ο j

-G-O-,

Il! 0

-C-O- j

Il ο

-C-O-

Il ο

-G-O-;

HI

O!

^GH 3

Supreme Court,

OGH _x

GH,

Ά-2

-O*

GH

Cl

-CH, -CN -H

—Η

-CH

-GN

-CN -H

-CH, -GN -H

-CH, -CN -H

-CH, -CN -H

-CH, -CN -CH

-CH,

209845/1151

- 51 -

Ref. 29o8

No.

99-

loo.

Ιοί.

1ο2.

1ο3.

! f
! ι
Η, ο-ίΓν: -CO-
Il Il
0 H, C- (V ' -CO-
Il 3 V ^ / Il
0 -CO-
Il
0 ο -CO-
Il
0

-CN ^; -H

OCH

-CH, t -CN, -H

OCH

-CH ₃ I -CN

Io4.

Io5.

I06.

Io7.

I08. OH

CH

o-i

O-

-C-O-

Il ο

-C-O-

Il

0 -C-O-

Il

0 -C-O-

-CN ^! -H

-CN -H

OCH, ^CH 3 j

CH, CH ₃ !

-CH ^,! -CN! -H

Cl

-C-O-

Il

0 -C-O-

Il

Br

Cl

Cl

-CH

-CN ι -H

-CN -CH,

-CH ₃ , -CN

-CH

-CN

209845/1151

Ref. 29o8

Uo.

R-.

9.

Ho

111.

112.

113.

ό-

Cl

CH,

CH,

hC-0-

Il

J-C-Q-

• Il

S-C-O-

i Il I ο

-CO- Il

Br

CH,

CH,

114. H, C0- ('
3

115.

116.

117.

H ₅ C-

jH CO- ^

Br - </

OCH,
/ '

OCH

-C-O-

Il

■ 0 HO-O-

■ Il

31

f-σ-ο-

Il ο

-G-O-

Il 0

-CH

-CH "i -GH

3 ι

-CH, -CN -H

-CN! -H

-CH

-CN -H

-CH, -CN j -H

-CN -H

-CIi

-H

-CH ₅ -CN

-CH, -CN

-H

-H

2098A5 / 1161

Ref. 29o8

No.

H-,

Rr

118.

119.

12o

122

123

124

NG

Eq

Eq

Eq
Cl

Br

CH.

H,

Supreme Court,

OH

¹²⁵

! 26

-G-O-

Il 0

-C-O-

Il 0

-C-O-

Il 0

-C-O-

Il ο

-C-O-

Il ο

-0-0-

-0-0-

-0-0-

-CKO-Il 0

-CN -H

-0Έ -H

-CH ₃ -CN -H

-GH ₃ -GN -H

-GH, -CN -H

-CH, ί -GN -CH,

-CH, -CN; -OH,

-GN ι -CH ₃ -GN -H

209845/1151

Ref. 29o8

Uo. R _n

Cl

CH,

129 ^.:

oil

Supreme Court,

13o.

131

132.

133.

134.

135.

136.

Eq

Cl-

OCH-

-Ö-

01

H ₃ GO

-o-c-

-0-0-

-oc-Il 0

-0-0-

-0-0-

WHERE

-0-0-

-0-0-

0 -0-0-

0;

'Il 0

■ ö

-CH, -CU -H

-CH, -CN -H

-CH, -CW -H

-CH, -OH -H

-ON -H

-OH, -CN -H

-H -ON -H

-H -CN -CH

-CN -CN -H

-OG ₂ H ₅ -ON ■: -H

20984571151

Ref. 29o8

137.

138.

139.

14ο.

141

■ ^H5 °° Ah

142.

-0-0-

'Il ο

-0-0-

Il ο

-0-0-

Il ο

-0-0-

Il ο

-0-C- i

Il 'ο

-0-C-

-COOC ₂ H ₅ -CN -H

-CN -H

-CH ₂ -CH ₂ -OH -CN -H

-CHo-CHo-CN -CN -H

-CH ₂ -CH ₂ -O-OC-CH ₅ -CN -H

-CH ₂ -CH ₂ -OCH ₅ -CN -H

143.

144.

145.

146.

O-

CH _x
j

CH

Cl

H ₅ C-

-0-0-

Il 0

-o-c Il 0

-0-0

Il 0

-o-o

Il 0

CH ₅
-CHo-CHo-N <-CN -H

CH

-CH = CH ₂

-CN -H

f:

-C = CHo -CN -H

-CH ₂ -CH ₂ -CH ₂ -CH ₃ ! -CN -H

209845M151

Ref. 29o8

No.

R-,

147.

148.

149.

15o.

151

152.

153.

154.

155.

O-

H,

GH,

H,(

-0-C-

Ii ■ ο

-C-O-

Il
0

-C-O-

Il

0
-CO-

Il

0 -C-O-

Il

0 -C-O-

Il

-0-0-

Il . 0

-o-c-

Il 0

-0-0-

Il

O - (D

-CH,

-l

■ CH

sr

HC-CH

-CH -H

-CN -H

-OD "-H

-CN -H

-CN -H

-CN -H

-CN -H

ι -CN -H

-CN -H

3.56.

-0-0-

Il o

-CN. -H

209845/115

No. Rn Η / ·

- 37 -

Ref. 29o8

157

158.

159

16ο.

161.

162.

ν

164.

165.

-0

-ο-σ

166

■ ^H 3 ° -Q

-C-O-

Il ο

-C-O-

Il

O -C-O-

Il ■

O -C-O-

O -C-O-

Ii

O -C-O-

Il

O -0-0-

-B-Oll O

CH

CH

OCH

; -COOC ₂ H ₅

-CE

-CH ₃ j -CO-CH ₃

-CH

CH

-CH

-CH

-οο- / ηΛ

-CH

-CH, j -CO-NH ₂

-CH ₃ i -CO-NH-CH

-COO-CCH ₂ ) ₃ -CH ₃ -H

-CO-CCH ₂ ) ₅ -CH ₃ -H

I-H

209845/1151

Ref. 29o8

Hb. R

H ₅ C

167.

168

169

17ο.

171.

172.

173.;

174. »

175. '

176.! / i

CH,

-Q-G-

: Il i

-0-C-

■. Il

■ ο

O r ° T

CH,

GH.

ξ-σ-ο-:

J Il j

ιι ·

ο

-CO-! ο

¹⁷⁷ · κ, ο-fy

0! -Q-G- j

-O-G- ι

GH,

-CH, -CO-N

CH,

-CH ₃ -GO-BH- (CH ₂ ) 5-CH ₃ -H

-CH, -CO-N

-GH,

-GH ₃

G ₂ H ₅

-GO-H (

CH ₂ -CH ₂

-GO-HH- / \
-SO ₂ -CH ₃
j -SO ₂ - (CH ₂ ) ₃ -GH ₃

^: σι

-GH,

-0

-CH ₃ -SO ₂

-GH, I -SO ₀ -HH

-GH,

. -H

3 i -S0o- (> -Gl -H

-SO ₂ -HH-CH ₂ -CH ₃ ; -H

20984

Ref. 29o8

R-,

178.

H ₅ C ₂

l-o-c-

Il ο

H,

179. '

18o. '

181.

182

183.

184

185

186.

187. H, 0

188

r °

—C-

Il ο

M) -C- Il ο

M) -C-

: Il

ι ο;

i ι

L-O-C- I

; n

0 i

ι ^;

-C-O-

'■ Il

0 -C-O-

-o-c-I ■

! ο

I hO-Ct

¹ n

¹ O

Lo-C-

Il

k> -c-

Il O

-CH,

-CH,

-SO

CH,

_γ ν (1 '

^L 2

-SO ₀ -UV
^ Λ

-SO

CH ₂ -CH ₂

, -υ / hh

CH ₀ -CH,

CH

-

-CH, -CH,
3

-CH,

-CH,

- (CH ₂ ) ₂ -CH ₅

- (CH ₂ ) ₅ -CH ₅

-CH ₂ -CH ₂ -]

V_ i - ^CH "

209845 / 1IF

- 4ο -

Ref. 29o8

S-,

189

19ο.

191.

192.

193..

194.

195.:

196. j

197

198

C-O-:

Il O

C-O-

Il

ο!

ο-σ- j

Il ^;

O:

ο - °

-0-C

Il ö

-CO- Il ο

-c-o-

Il 0

-0-C-

ΓΑ! -

C-O-

Il ο

O ί " ⁰ T ^!

-CH,

-CH.

-CH,

-E

-H

C ₂ H ₅ ;

-H

CH ₂ -CH ₂ -li <

-CH,

CoH _n

! -CH ₂ -CH ₂ -H / I -H

, -CH ₂ -CH ₂ -

C ₂ H ₅

-0-C- I

-CH,: -H

-CH,: -H

-CH ₂ -CH ₂ -CH ₃ -H

-CH, -CK

-H

-H

-H

-H

'-UH;

209845/1151

Ref. 2908

No. H,

199

f ~ X

-C-O-

200th! H ₃ C-

201. / ~ \

202

203.

20%.

205.

206

207.

208.

I X =.

-o-c- -o-c-

Il O

-o-c-

-o-c-

-C-O-

-G-O-

-0-C-

Il

-0-C-

Il O

e \

f "\ -CHg-CH ₂ -CH ₂ -CH ₅ j -CN -NH-CH ₃

-CH,

-CN -H-

CH, CH,

-CH.

-CN τ-

-CH

^C 2 * 5

-chI-n ^a

₂ -CHg

-GH,

-OH, -CH.

-CH,

-CN j -

-CN -CHg-GHg-OH

-CN ^ CHg-CH ₂ -OCH ₃

-CN -CHg-CHg-CN

-CN -CHg-CH ₂ -O-OC-CH ₃

-CN -

209045 / 1ISI

3ef. 2908 Z

21Θ, 211 _β 212.

213.

214.

215

216.

■ β-5-Ι. / Λ.

11 I.

-CH-

-C-O-II 0

X = /

-G-C-

19 0

-CH,

-CH,

- »GH-

"it,

■ J

-O

»0H,

-CH.

-CH! -CH ₂ -CH ₂ -CH ₂ -CH- -CH | -CH ₂ - (CH ₂ ) ₄ -CH ₃ -CH

-CH

-CH

-CH

-CH

^H 3

-CH

-CH

V = /

-Qr-

-CH

-ir

CH = CH

CH = CE

4 5/11

No. »<

- 43 -

Kef. 2908 Z

219. j /

220. \ f

221. i

222.

* -

Il O

-o-c-

11 0

• 0 — C-

Il 0

-O-Q-

223.1 / "" ν. '-C-O-

224.

225

Il \

-CH-

-CH,

-CN

-CN

-CN

-CH ₂ -CH ₃

-CN

-H

-CH ₂ -GH ₃

-H

/ \ ^: "" ΊΤ ί ο

y \ _

226.

228

-C-O-

ft

-CH

-CH.

CH,

-CH

^3H 3

f ~ \ " -CH ₂ -CH ₂ -CH ₃ -COOCgH-

-CH,

-CO-NH,

HC ^ CH

.i

-CH ₂ -CH ₃

-CH,

-CH,

-CH ₂ -CH ₃

-GH,

-CH,

209845/1151

2120095 ^Η 2 - 44 Β, - χ Y Ref. 2908 No. T ⁰ -
0 O -CH ₃ CH-
-CO-N ■ *
CH ₃ Z 229 · ( -0-C-
0 -CH ₃ -SO ₂ -CH ₃ -CH ₃ 230 • ί 0 ■ ο -GH ₃ -CH ₂ -CH ₃ 231 • ί
\ = -0-C-
0 -ο -OH, CH,
-SO ₂ -N >
^Δ CH ₃ -CH ₃ 232 ■ ί -CH ₃ example > > V > 2

a) 22 _f 7 wt. parts of 4-amino-benzoic acid 4'-methyl-phenyl ester in 150 wt. parts of glacial acetic acid with 34.2 wt. parts
Nitrosylsulfuric acid 41.3 # Dei 15 ° C diazotized. The clear diazo solution is then allowed to flow into a solution of 16.4 parts by weight of 1,4-dimethyl-3-eyan-6-hydroxy-2-pyridone in 400 parts by weight of water and 122 parts by weight of 33 ° Be sodium hydroxide solution. The reaction temperature is increased during the coupling by adding 500 parts by weight of ice
0 to +5 ⁰ C held. After the coupling has ended, the resulting dye is filtered off with suction, washed neutral with water and dried. It is a yellow powder that dissolves in concentrated sulfuric acid with a reddish yellow color.

2098-5 / 1151

- h5 - Ref. 2908

b) 30 parts by weight of the dye obtained according to Example 2a) the formula

CH,

are in fine distribution of a printing paste, the 45 »0 wt. Parts of locust bean gum, 6.0 parts by weight of sodium 3-nitrobenzenesulfonate and 3.0 parts by weight of citric acid Contains 1000 parts by weight, incorporated. Hit this printing paste is obtained on a polyester thread after printing, drying and fixing in the heat-setting frame for 45 Seconds at 215 ° C, rinsing and finishing as in Example Ib) described, a yellow print of very good Authenticity properties "

When printing on triacetate fabric, the dye provides when it is used in the form of the above printing paste, and the printed fabric after drying for 10 minutes 1.5 atmospheres steamed, rinsed, soaped, rinsed again and dried, a yellow print of high lightfastness.

In the following table 2 further dyes according to the invention are given which dye on polyester material or deliver prints with also very good fastness properties.

- '46 S? ato rush 2

X-

HO -K ^ - ¹ ^ © Z

Xn.

H 0

-Q-C-

-CN

-CH, -CH,

-CH-

\ -CE ^

. "/" \ -CE,

-A

it"

JX -CM,

CM

-SK

-CF

-CE

-SIf

-CH- -CH, -GH,

-CH,

-CH-

-CH,

2 0 9 8 4 5 η 1 5 1

Ref. 2908 Z

10. H-C

f ~ \

-0-C-

'ί

V) -CH ^ -CN -CH,

-0-C-

-CN -CH,

OCH,

ο-

OCH ₃

D-

.0-C- J ~ \

ο W.

-CH, -CN

-o-c-

i O

-CH, -CN

OCH,

OCH,

-0-C-

Ii

-CH, -CN

OCH,

OCH,

o-c-ό

-CH, -CH,

-CN -CH,

-CH,

-CN -CH,

-CH,

-CN -CH,

-CN -CH,

19. H-CO- / '^ -

-0-C- // \ -CH, O

-CN -CH,

20984 R / 1151

No. Ε · _Η

- 48 ^ß 2 »3

Yeast. 2908 Y Z

20. H ₃ CO- / \

-0-C-

.-CH, -CN -CH.

21.

Cl

22nd

23

24.

25th

26th

27

28th Cl

29. Cl-

Cl

Cl

Cl

"X

-o-c-

-0-C-

-O-C-

- ⁰ K-

-O-C-

-O-Ci

-O-CJ O

A-

/ \ _ · -GH. * -CN -CH,

-CH, -CN -CH,

-CN -CH,

-CH, -CN -CH,

-CN -CH,

-CH, -CN -CH.

-CH, -CN

-CH, -CN

-CH, -CN

209845/1151

Ref. 2908 Y Z

32. / \

-C-O-

! I 0

C 0

-CH,

-CN -CH-

-CH, -CN -CH,

-CH, -CN -CH,

CH

CH

CH

CH,

A ..

CH ₅

C-O

IS 0

C-O

i '

C-O

H - 0

C-O 0

-C-O-0

-C-O-

Ii

-CH, -CN -CH,

»CH, -CN -CH,

-CH,

-CE

-GH,

-GN -CH,

/ \ -CH, -GN -CH,

-CH, -CN -CH,

-CN -CH,

-CN -CH,

20S845 / 1151

21200S

Ref. 2908

No. ε,

40. H ₃

-ο-β-

O O

-CH- -CN -CH,

41.

Tbsp

-C-O-

Vi Q

\\ -CE ₃ -CN -CH,

42. E,

rv.

CS ₃

-CN -CH,

> 43,

44 ;.

QCH ,.

-C-O-

I!

G-O-

I «

-CH,

-CN -CH,

-CN -CH,

45.

46.

47.

-G-O-

O \ - /

-GH- -CN

-CB-

-CE ₃

-CN -CH-

-CN -CH

48,

-CN

49 · E-i

-CE-

-CN -CH,

3-0-

-OM -CH

No.

Ref. 2908

51. H ₁ -CO // ^S. Cl -CO-
0 O -CH ₃ -CN Cl I. I. 52. Cl -CO-
0 -CH ₃ -CN 53. Cl
■ r \ I. -CO-
0 Ö -CH ₃ -CN Cl ^S \ _- rr / 54. Cl -CO-
0 4 \ -CH ₃ -CN <> 55. -C-O- j / \ -CH ₃ -CN 0 56. Cl-J \ -C-O- / rs -CH ₃ -CN 0 57. -CO-
0 O -CH ₃ -CN 58. -C-θ- O -CH ₃ -CN 0 1 / 59. -CO-
0 -Ö -CH ₃ -CN

60. Cl

. -ι

-C-O-

-CN -CH ₃

209845/1151

2120035

Ref. 2908
Y Z

-CN

-CH,

62. H ₃ C '- /

63. H ₃ CO: ·

-0-CJ. j / V-CH ₃ -CH, -CN

-CN

—CH «

-CH,

6k. ei - 7 - -ο-ς- ..// —gh. -CN

-CH

66. H _1x C J V 67.

-0-9-

-0-C-ä-0

-O-Ci

./ N

68. Cl

70. HC Jf

-0-C- ö

-0-C-O

-0-C-O

^0Η ι ·

-CH, -CN

-CH ^ -CN

-CH, -CN

-CH, -CN

-CN

-CN

-CH,

-CH,

-CH,

-CH,

-CH.

-CH,

2 0 98-45 / 1

212Ö09S

Ref. 2908 Y Z

71. H ₃ CO- ^ ^x > -

-0-C-

Ii

OCH

-CH, -CN -CH,

72. Cl

-O-C

\ O OCH

-CH, -CN -CH,

73. // ^

76. Ci

f '\

-o-c-

Il O

.0-C ₁ -

-o-c-

«O-c

•1..

OCH,

GOH

0%

-0-0-

! (—V

-CE, -CN -CH,

-CH, -CN -CH,

-CH, -CN -CH,

-CH, -CN -CH,

-CH, -GlJ -CH,

78. H ^

.o-c -GH, - ■ -GM - -CH,

-O-C-

, ei -gh

-CH.

so. ci -; ■ ('■ ·

-CE ₃ -CN -CH ₃

No. "E ₄

JU-,

Ref. 2908 Z

81

82.

83.

> S4u

85.

87

SS,

.YY?

-o-c-

-o-e-

86 _e / ~ X- ~ -0-f

-0-6-

-CI

-CM

-CE, -CN

-CK

-CH- -CN

-CE ₃ -CN

-CIf

-CH

-CM

-CH-

-CH,

-CH.

-CH,

-H

-H

-CE,

-E

209845/11 ^ 1

2120Π3

No.

- 55 -

Ref. 2908 Z

89 90 91. 92. 93. 94.

-cc-

( V

-0-C-

I! 0

-0-C-

-GH, -CN

-CH, -CN

/ TX

-C-O-

ft

-C-O-

-CH-

-CH-

95. H, C- <Q- -CO-, ^ _β

-CH- -CN

96. H ₃ C.

/ V -C-O-0

97.

-C-O-

-CN -H

-CN -H

-CN -H

-CH, -CN -H

-CN -H

-CN -H

209845M1S1

No.

- 56 -

Ref. 2908 Y Z

98. H-C- / V-

-C-O-0

-CN

-H

99. H ₃ C

-C-O-

Il O

-CN -CN

-H

-H

-C-O-

\ - 0

-C-O-

Il ·
0

-C-O-

f \ -CH,

-0-0- _f \ -OH ₃

⁰ O -CN -CN

-CN

-CN

-H

-H

-H

—CH »

203845 / 11S1

2120G95

Ref. 2908

ΊΤ ·. E ₁ R ₂ "I ₃

XT

105.

-C-O-

ii

-CN -CB,

106.

rON -CE,

-CE ₃ -CN -CE ₃

^1ββ

.C-O-O

-CE ₃ -CN

O-

-CE ₃ -CN -CE

110 ·

-OE ₃ -ON -CB ₃

in.

112.

C-O-

,; 0

-CE, »CN -CB,

203845/1151

-5ε -

No. B ₄

fief. 2908 T Z

115

-CE- -CN

114.

I- ⁰ - / Λ

-CH,

-CN -H

115

Gl -4 Λ- Cl -CH,

-CN -H

# 16.

-C-O-0

117 "

118

Cl

■ s

"il

CJ

= 3

-CN -CH "

-CN -CE «,

-CN

119a

■ © ■

■ you

120 »·

-CM -E

-GN

No.

- 59 - ^l 2 »5

Ref. 2908 ± Y Z

121. Cl

122.

Cl

-o-e-

_ / "" \\ -CH ₃ -CN

-0-C-

/ i

-CH, -CN

-H

-H

123. f ~ \

124.

.0-9- o

■ o-e *. ο

-CH ₃

-CN

-CH, -CN

-CH,

-CH,

125. fS ^

126. ^ ^^ 127.

H ₃ CJk Ji

128. 129.

• ΐ ^ ϊ-

Cl

-0-C-0

-0-iC-

-o-c-

-CH ₃ -CN -H

-CH-

-CH-

-CH-

-CN

-CN

-CN

-CH-

-H

-H

-CH, -CN -CH,

209845/1151

No.

Ref. 2908 Y Z

Cl

130

₀₁ "T / _>'■

-CH, -CN -CH,

131

■ 0-C-O

-CH, -CN -CH,

132.

-0-C-

-CH, -CN -CH,

i L!

133. / "V.

-o-c-

TC

135.

-CN -CH-

-CN -CH,

-CN -CH,

136.

137

-C-O-0

-0-C-0

-CN -CH,

-CH ₃ -COOC ₂ H- -H

138

0-C-0

-CH ₃ -CO-CH ₃ -H

2 0 3 8 h 5 / T 1 P

2120ÜÜ5

Ref. 2908

No.

B ₁ R

139.

■ 0-C-

il

-CH ₃ -CO-NH ₂

-CH,

140

141. / Λ

142.

-0-C-

Il O

-SQ ₀ -CH, - —CH. »

-CH- -SO ₀ -N '3 <£

-H

-GH ₃ -CH ₃

-H

143. r ^^ V ^ r- -C-O-

-CH ₃ - (CHg) ₃ -CH ₃ -H.

144. f- \

145.

-o-c-

-CH ₃ -CH ₂ -CH ₂ -:

^C 2 ^H 5

/ ^C 2 ^H 5 -CH ₀ -CH ₀ -N / ^ ^p -H

^C 2 ^H 5

146.

-C-O-

-CH ₃ -CH ₀ -CH ₂ -N

147.

-C-O-.

β 0

-CE. * -M

-H

0 984 57 1 15.1]

Ref. 2908

148. H-C_ / \ -0-C-3 \ / §

-H -H

149.

150.

0-C-

151

"T

-CH- -CH -CH ₂ -CH-

-N:

la. ί * 13Γ - tfyjFT ^ TB "^ H OTT λιττ" ^

152.

-CH -CH ₂ -CH ₂ -CN

153. <r 7- -G-O-Cl / \ C1

-GH- -CH

<D

154.

CH-3

Ϊ-G-

-CH

-CH

155. / ^ V- ° -ξ- "TT ^

-CH - /

-ö-i

OCH-

20S845 / 11S1

212U095

- 63 -

Ref. 29O8 T Z

157

Cl

-CH,

-CN

HC - CH

H H

-CH ₀ - C CH 2 \ ₀ /

158.

159

160. V_ -CH ₂ -CH ₂ -CH ₃ -CN

-CH,

-CH ₂ -CH ₂ -OCH ₃ -CN

-CH ₂ -CH ₃ -H -CH ₂ -CH ₃

I6I.

- ⁰ T -C -CH ₃ -CH ₂ -GH ₃ -CH ₃

162.

-CH ,, -COOC ₂ H ₅ -CH

163. H.

₃ -CO-NH ₂ -CH ₂ -CH ₃

-CH ₂ -CH ₃ -SO ₂ -CH ₃ -CH ₂ -CH ₃

-CH

~ ^CH

CH

-CH, -SO ₉ -N ^ ^J -CH

* CH

2038 A 5/1151

Claims (5)

- 6k - Ref. 2908 claims 1. Water-insoluble monoazo dyes of the general formula R ₁ -B ₂ -R ₃ -N = N, Y HO ^L N ^: 0 wherein R 1 is free from water-solubilizing groups aromatic residue, H _{2 is} a -0-CO- or -CO-O- group, R- an aromatic radical free of water-solubilizing groups, X hydrogen, a cyano, an alkoxy, a Carboxy, optionally branched and / or substituted alkyl, optionally branched and / or substituted alkenyl, optionally substituted cycloalkyl, aralkyl, aryl groups or a heterocyclic radical, Y is hydrogen, one cyano, one optionally branched and / or substituted alkyl, optionally branched and / or substituted alkenyl, optionally substituted cycloalkyl, aralkyl, aryl groups or the radicals -COOR. , -COR ₁ -, -CON ^R 6, R R -SO ₀ R- or -SO ₀ -N 6, where R., and R- a R ₇ Alkyl group, R- also an optionally substituted cycloalkyl, aralkyl = -, or aryl group and R ^ and R _{7 are} hydrogen, a. Alkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, aralkyl or aryl groups, the alkyl radicals Rg and R ₇ also being connected directly or via a heteroatom
could be, Z is hydrogen, an optionally substituted one
Amino, optionally branched and / or substituted alkyl, optionally branched 2 0 9 R 4 5/1 1 5 1 - 65 - yeast. 2908 and / or substituted alkenyl, optionally substituted cycloalkyl, aralkyl, aryl or a group heterocyclic radical mean. 2. Water-insoluble monoazo dyes according to claim 1, characterized in that R. a phenyl radical, which may be replaced by methyl, Ethyl, methoxyl, ethoxyl and / or halogen can be substituted, R, an o-, m- or p-phenylene radical, which optionally can be substituted by methyl, ethyl, methoxyl, ethoxyl and / or halogen, X is a methyl or ethyl group, Y is a cyano group, Z denotes hydrogen, a methyl or ethyl group. 3. Process for the preparation of dyes of claims 1-2, characterized in that an amine of the general formula is used R ₁ -R ₂ - R ₃ - NH ₂ II diazotized and with a € -hydroxy-2-pyridone derivative of general formula J in ^ 0 couples, where R ₁ , I ₂ , * R-, X, Y and Z can have the meanings given in claims 1-2. 4. A method for dyeing and printing synthetic, hydrophobic materials, characterized in that one a dye according to claim 1 or 2 is used for this purpose. 209R45 / 1151 - 66 - Ref. 2908 5. Synthetic, hydrophobic materials dyed or printed according to the method of claim 5 209845/1151 ORJGlNAL INSPECTED