DE2941512A1 - NEW MONOAZO DYES AND THEIR USE - Google Patents

Description

The invention relates to new monoazo dyes, which are disperse dyes, very specifically monoazo dyes with a substituted phenylazo radical and an acylamidotetrahydroquinoline coupler radical with ether substituents and the use of such dyes for dyeing of textile structures, in particular made of polyesters.

The monoazo dyes according to the invention have the structure evident from the claims.

The monoazo dyes according to the invention produce on textlien Formed, for example from polyesters, e.g. polyethylene terephthalate) yellow to turquoise shades. The dyes produce extremely strong colors, can easy to dye and have excellent absorption and fastness properties, especially sublimation fastness properties on polyester fibers, as can be seen from tests results, which are carried out according to the standard procedures, which are described in the "Technical Manual" of the American Association of Textile Chemists and Colorists. For example, the monoazo dyes according to the invention have Compared to the azo dyes of US Pat. No. 2,249,774, they have more favorable fastness properties and produce stronger dyeings on polyester fibers. Also have the invention Dyes have considerable advantages over the dyes known from US Pat. No. 3,635,941, since the dyes according to the invention Dyes can be colored on textile structures at comparatively lower temperatures, which is why they are particularly suitable for the exhaustive coloring of polyesters. Of Furthermore, the dyes according to the invention penetrate particularly easily and completely into fibers and thereby provide uniform, strong colorations, even at temperatures below those temperatures necessary for full

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Exhaustion of the dye liquor are required,

The dyes according to the invention correspond to the following general formula:

RC ₂ H ₄ OC ₂ H ₄ OR ⁵

where mean:

X is a chlorine, bromine or fluorine atom or one

Cyano, nitro, trifluoromethyl, short chain Alkoxy, short-chain alkoxyalkoxyalkanoyloxy, short-chain alkylsulfonyl, arylsulfonyl, Chlorarylsulfonyl, a short-chain alkylsulfonyl substituted by at least one halogen atom, short-chain alkoxycarbonyl, aroyl, aroylsulfonyl or short-chain alkanoyl radical;

η = 1, 2 or 3;

A is an acyl radical;

R, R and R, which can have the same or different meanings from one another, each represent a hydrogen atom or a short-chain alkyl radical;

R is a hydrogen atom or a short-chain one

Alkyl, short-chain alkoxy or short-chain alkanoyloxy;

R is a hydrogen atom, a short-chain alkyl

or short-chain alkoxy radical and

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R 'is a short-chain alkyl or cyclohexyl radical.

The acyl radical represented by A can be, for example: a formyl, short-chain alkanoyl, aroyl, cyclohexylcarbonyl, short-chain alkoxycarbonyl-, aryloxycarbonyl-, short-chain alkylsulfonyl-, short-chain alkoxysulfonyl-, cyclohexyl sulfonyl, aryl sulfonyl, aryl oxysulfonyl, CArbamoyl, short-chain alkylcarbamoyl, arylcarbamoyl, sulfamoyl, short-chain alkylsulfamoyl or furoyl radical.

The short-chain alkanoyl radicals can optionally be substituted be, for example by at least one halogen atom or at least one aryl, cyano, short-chain alkoxy, benzyloxy, short-chain alkylthio, short-chain alkylsulfonyl or short-chain alkoxysulfonyl radical.

The alkylsulfonyl and alkoxysulfonyl radicals can optionally also be substituted, for example by at least one halogen atom or at least one cyano or Hydroxy radical. The alkoxycarbonyl radicals can also be substituted, for example by hydroxy, short-chain alkoxy, short-chain alkoxyalkoxy and / or cyano radicals.

Examples of alkanoyl, alkoxycarbonyl, alkylsulfonyl and alkoxysulfonyl radicals, for which A can stand, are acetyl, Propionyl, butyryl, cyanoacetyl, chloroacetyl, trifluoroacetyl, phenylacetyl, methoxyacetyl, methylthioacetyl, Methylsulfonylacetyl, methoxycarbonyl, propoxycarbonyl, butoxycarbonyl, methylsulfonyl, ethylsulfonyl, propylsulfonyl, Butylsulfonyl, 2-cyanoethylsulfonyl, 2-hydroxyethylsulfonyl, 2-chloroethylsulfonyl, methoxysulfonyl and Ethoxysulfonyl residues.

The aryl part of the arylalkanoyl, aroyl, aryloxycarbonyl, Arylsulfonyl, aryloxysulfonyl and arylcarbamoyl radicals is monocyclic and consists, for example, of an optionally substituted phenyl radical, which is, for example, substituted

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can be ated by short-chain alkyl radicals with, for example 1 to 3 carbon atoms, short-chain alkoxy radicals and / or Ilalogen atoms.

The aryl radicals can typically consist of tolyl, Anisyl, p-bromophenyl - o <! Er o, p-dichlorophenyl radicals exist.

Typical examples of alkylcarbamoyl and alkylsulfamoyl radicals, can stand for A are, for example, Uimethylcarbamoyl-, Ethylcarbamoyl, propylcarbamoyl, butylcarbamoyl and dimethylsulfamoyl radicals.

Typical short-chain alkyl radicals are methyl, ethyl, propyl, isopropyl, isobutyl and rutyl radicals. Typical short chain Alkoxy radicals are methoxy, ethoxy, propoxy and butoxy radicals.

Examples of suitable alkanoyloxy radicals are acetoxy, Propionoxy, butyroxy and isobutyroxy radicals.

The term "short-chain" used here denotes radicals with a carbon content of 1 to 6 carbon atoms.

Particularly preferred dyes according to the invention can be represented by the following formula:

C ₂ H ₄ OC ₂ H ₄ OR-

where mean:

a chlorine or bromine atom or a cyano radical;

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R ¹ and R ³ R ² and R ⁴ R ⁵

a nitro or cyano radical;

a short-chain alkanoyl, benzoyl, short-chain alkoxycarbonyl, short-chain alkylsulfonyl or short-chain alkylcarbamoyl radical;

a methyl radical or if R or R represent hydrogen atoms, R is a short-chain Alkyl radical;

each represents a hydrogen atom or a methyl radical;

each a hydrogen atom and a short-chain alkyl radical.

The dyes according to the invention can be prepared by diazotization of the arylamine radical and coupling with the tetrahydroquinoline radical by customary known processes.

In the following Examples Λ to C, the preparation of some coupler compounds is first described, which are used for Let the preparation of dyes according to the invention be used.

Example A.

87.5 g of 2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline, 127 g of 2- (2-ethoxyethoxy) ethyl chloride, 58 g of anhydrous sodium carbonate and 7.5 g of sodium iodide were heated to one temperature for 5 hours heated from 190 to 200 ^{0 C.} The salts were then extracted with water and the organic layer was distilled. The reaction product, namely 1- / ~ 2- (2-Äthoxyäthoxy) -äthyl_7-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline was at a pressure of 0.3 to 0.4 mm at a Subtracted temperature of 139 to 154 C. 58 g of the reaction product were then slowly added to 150 ml of 100% sulfuric acid at about 10.degree.

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Then a solution of 13.5 g of 98% nitric acid and 17 ml of a 100% sulfuric acid were added dropwise at 0 to 5 ° C. After an additional hour, the Mixture poured into an ice-water mixture and neutralized with a 50% sodium hydroxide solution. It was then extracted with 300 ml of isopropanol. The solution of the 7-nitro compound was then in the presence of a faIladium-carbon catalyst hydrogenated at 75 ° C and a hydrogen pressure of 35 kg / cm. After removal of the catalyst, the solution was the Treated 7-amino compound at 5 to 10 C with 20 ml of acetic anhydride, which were added over 15 minutes. After further The excess acetic anhydride was hydrolyzed with water for 15 minutes, after which the solution was evaporated to dryness became. The reaction product, namely 7-acetamido-1- / ~ 2- (A "thoxyethoxy) äthyl_7-2,2,4-trimethyl-1, 2, 3, 4-tetrahydroquinoline was dissolved in a sufficient amount of acetic acid, to produce 400 g of coupler solution.

Example B.

6.97 g of 7-acetamido-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline, 7.63 g of 2- (2-ethoxyethoxy) ethyl chloride, 3.18 g of anhydrous sodium carbonate and 0.45 g Sodium iodide was heated to 150 to 160 ° C for 9 to 10 hours. The reaction mixture was then slurried with 20 ml of water and neutralized with a 10% HCl solution and then poured into 500 ml of a 2% HCl solution, whereupon 15 ml of acetone were used to rinse out the flask. The solution was then extracted with hexane to extract excess 2- (2-ethoxyethoxy) ethyl chloride. The aqueous layer was then neutralized with ammonium hydroxide to recover the reaction product. The reaction product, namely 7-acetamido-1- / 2- (2-ethoxyethoxy) äthyl_7-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline was isolated in the form of a semi-solid mass. This was then slurried in water, which was then poured off. It was then dried until a constant weight was achieved.

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Example C

The procedure described in Example B was repeated, but this time using an equivalent amount of 2- (2-isobutoxyethoxy) ethyl bromide instead of 2- (2-ethoxyethoxy) ethyl chloride was used. The reaction product was 7-acetamido-1- ^ ~ 2- (2-isobutoxyethoxy) ethyl / -2,2,4-trimethyl] -1,2,3,4-tetrahydroquinoline obtain.

Examples of other alkylating agents also used are: 2- (2-methoxyethoxy) ethyl bromide; 2- (2-methoxyethoxy) ethyl chloride; 2- (2-ethoxyethoxy) ethyl bromide; 2- (2-isopropoxy methoxy) ethyl chloride; 2- (2-butoxyethoxy) ethyl bromide; 2- (2-butoxy3thoxy) ethyl chloride; 2- (isobutoxyethoxy) ethyl chloride; 2- (2-tert-butoxyethoxy) ethyl chloride and 2- (2-pentoxyethoxy) ethyl bromide.

The following examples are intended to illustrate the preparation of Illustrate dyes in more detail.

example 1

2.08 g of 2-cyano-4,6-dinitroaniline were at 15 ° C in 75 ml of a 70 Hgen H ^ SO. slurried. The mixture was cooled to -2 ° C., whereupon a solution of 0.72 g of sodium nitrite in 5 ml of concentrated H ₂ SO ₄ at a temperature of -2 to ⁰ ° C. was added. The reaction mixture was ^{stirred at a temperature of 0} ° C. for 3 hours and then added to a solution of 3.48 g of 7-acetamido-1- / ~ 2- (2-ethoxyethoxy) ethyl_7-2,2,4-trimethyl-1 , 2,3,4-tetrahydroquinoline, dissolved in 100 ml of concentrated H_SO. added at below 10 ° C. After coupling for one hour, the dye was precipitated by pouring it into water. Fr was filtered off, washed with water and air-dried. The reaction product, 6- (2-cyano-4,6-dinitrophenylazo) -7-acetamido-1- / ~ 2- (2-ethoxyethoxy) ethyl_7-2,2,4-trimethyl-1,2,3,4- tetrahydroquinoline dyed threads and fibers made of polyester in a strong greenish-blue shade. The colors showed

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excellent lightfastness properties and sublimation fastness properties on.

Example 2

The procedure described in Example 1 was repeated with the exception, however, that this time 3.76 g of 7-acetamido-1- / 2- (2-isobutoxyethoxy) ethyl 7-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline instead of the coupler used in Example 1 were used. The dye obtained, namely 6- (2-cyano-4,6-dinitrophenylazo) -7-acetamicio-1- / 2- (2- isobutoxyethoxy) ethyl_7-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline dyed threads and fibers made of polyester in strong blue tones at.

Example 3

4.0 g of sodium nitrate were added in portions to 50 ml of concentrated H ₇ SO. given with temperature rise to 70 ° C. The solution was cooled and 25 ml of a mixture consisting of propionic acid and acetic acid (2 parts of propionic acid to 5 parts of acetic acid) were added below 10 ° C. The solution was then cooled to a temperature of 0 to 5 ^° C., whereupon 13.1 g of 2-bromo-4,6-dinitroaniline were added. Then another 25 ml of the described acid mixture of 2 parts of propionic acid and 5 parts of acetic acid were added and 10 g of ice. After 3 to 4 hours stirring at 0 to 10 ⁰ C, the üiazoniumlösung in portions was added to the coupler solution. The coupler solution was prepared by adding 160 ml of cold water to 120 g of a solution of 17.43 g of 7-acetamido-1- / ~ 2- (2-ethoxyethoxy) -ethyl-7-2,2,4-trimethyl-1,2 , 3,4-tetrahydroquinoline in acetic acid and then 10 g of concentrated H ₂ SO. and a sufficient amount of ice (130 g) to reduce the temperature to 0 ^° C. The temperature was kept at 0 to 5 ° C. during the coupling by means of a fis bath. After half an hour stirring at 0 to 5 ° C, a 50-celled NaOH solution was added with a sufficient amount of ice to prevent the temperature to 10 ⁰ C.

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rise. After the reaction mixture became only slightly acidic, it was poured into water. The reaction product was filtered off, washed with water and left in the air dried.

The monoazo dye obtained, namely 6- (2-bromo-4,6-dinitrophenylazoj- 7-acetaiaido-i- / 2- (2-ethoxyethoxy) -ethyl 7-2,2,4-trimethyl-1,2,3, 4-tetrahydroquinoline stained threads and fibers made of polyester in strong reddish-blue shades with good lightfastness properties and excellent sublimation properties.

Example 4

The procedure described in Example 3 was repeated, except that this time 100 g of an acetic acid solution with 18.83 g of 7-acetamido-1- / ~ 2- (2-isobutoxyethoxy) äthyl_7-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline instead of the coupler des Example 3 were used. The reaction product consisted of 6- (2-bromo-4,6-dinitrophenylazo) -7-acetaraido-1- / ~ 2- (2-isobutoxyethoxy) ethyl_7-2,2,4-trimethyl-1,2,3,4 tetrahydroquinoline. The dye dyed threads and fibers made from polyester in strong reddish-blue color tones, good lightfastness properties and excellent sublimation fastness properties at. The analogous 7-propionamido dye also stained threads and fibers made of polyester in reddish-blue shades.

Example 5

1.00 g of 6- (2-bromo-4,6-dinitrophenylazo) -7-acetamido-1- / ~ 2- (2-ethoxyethoxy) ethyl-7-2,2,4-trimethyl-1,2,3,4 -tetrahydrochinolin and 0.22 g Cuprocyanid were added to 20 ml of pyridine, whereupon the Reaktionsgemiich an hour, it was heated to a temperature of 112-114 ⁰ C. Then it was poured into water. The precipitated solid reaction product was filtered off, dissolved in hot 2-methoxyethanol and filtered. The filtrate was treated with hot water until crystallization occurred. The reaction product was filtered off

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isolated at room temperature. The reaction product, namely 6- (2-cyano-4, 6-dinitrophenylazo-7-acetamido-1- / ~ 2- (2-ethoxyethoxy) ethyl_7-2,2,4-trimethyl-1,2,3,4- tetrahydroquinoline was identical to the reaction product of Example 1.

Example 6

14 ml of Ν, Ν-dimethylformamide and 2.48 g of cuprocyanide were added to a solution of 1.35 g of sodium cyanide in 10 ml of water. The reaction mass was then heated to 45 to 50 ° C. until all of the cuprocyanide had dissolved. The solution was then added to a solution of 31.08 g of 6- (2-bromo-4,6-dinitrophenylazo) -7-acetamido-1- / 2- (2-ethoxyethoxy) ethyl-2,2,4-trimethyl 1,2,3,4-tetrahydroquinoline in 156 ml of N, N-dimethylformamide was added at 90 to 95 ° C. After one hour the mass was diluted with 312 ml of isopropanol. The precipitated dye was then ^{filtered off at 0} ° C. and washed first with 50 ml of isopropanol and then with water. The dye was found to be identical to the dye of Examples 1 and 5.

Examples 7 to 84

The dyes listed in the following table were prepared according to the procedures described in the preceding examples manufactured. The dyes obtained corresponded to the general formula given.

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2,6-di-CN-4-NO ₂ CH ₃ OSO ₇ Cli ₂ CO- 2, 2,4-tri-CH ^

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(+) When the radicals R, R, R, R ° and R are composed of hydrogen atoms
passed, the hydrogen atoms in the table
not listed.

The dyes according to the invention can be applied to textiles Color structures according to customary known methods which are known for coloring disperse dyes. Included can accordingly customary dyeing auxiliaries, such as surfactants, dispersants, carriers, thickeners and the like can be employed. the Coloring can take place at boiling temperature and atmospheric pressure or at higher temperatures under pressures above atmospheric pressure. The following example illustrates an applicable dyeing method using a carrier.

Application example

0.1 g of the azo compound from Example 1 were dissolved in 10 ml of 2-methoxyethanol. A small amount (3 to 5 ml) of a 3% strength by weight aqueous sodium lignosulfonate solution was added with stirring, whereupon the volume of the liquor was brought to 300 ml by adding water. 3 ml of an anionic solvent carrier (Tanavol) were then added to the liquor, whereupon 10 g of a fabric made of polyethylene terephthalate fibers were introduced into the liquor. First, the textile product was processed in the liquor for 10 minutes without the supply of heat. The actual coloration then took place at the boiling point for one hour. The dyed textile product was then removed from the liquor and ^{treated for 20 minutes at 80 °} C. in a solution with 1 g per liter of neutral soap and 1 g per liter of sodium carbonate. The textile product was then rinsed and dried in an oven at a temperature of 121 ° C. Then, 5 minutes, heat set at a temperature of 35O ⁰ C for.

The dyes according to the invention can also be applied, for example, to textile polyester products using a heat setting process color as described, for example, in US Pat. No. 2,663,612 and American Dyestuff Reporter ", 42, 1 (1953) are known. These methods can be achieved by using other dispersants, surface

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active compounds, suspending agents, thickening agents and
modify the like. The temperature and duration of the
The heat setting level can also be varied. The polyester fabrics, knitted fabrics, yarns, threads and fibers can optionally contain comparatively small amounts of other additives, for example brighteners, pigments, matting agents, inhibitors
and stabilizers included.

Although the azo compounds according to the invention are particularly suitable for dyeing textile structures made of polyesters, they can also advantageously be applied to other textiles
Coloring structures made of hydrophobic threads and fibers, for example on textile structures made of threads or fibers made of cellulose acetate and polyamides.

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Claims (10)

Registration number. 125 926 Eastman Kodak Company, 343 State Street, Rochester, New York State, United States of America New Monoazo Dyes and Their Uses PATENTANWÄLTE XXXOtMHSt H. BarteteDip) .- Chem. Dr. Brandes Dr.-Ing. Hekl Dipl.-Phys. Wolff 8 Munich 22. Thierschstrasse Te). <089) 293297 Telex 05 23325 (patwo d) Telegram address: wotffpatent, some postal check account Stuttgart 72) 1 (bank code 60010070) Deutsche Bank AG. 14/28630 (BLZ 60070070) Office hours: 8 a.m. to 12 p.m., 1 p.m. to 4.30 p.m. except Saturday, October 9, 1979 25/24 claims 1. J monoazo dyes, characterized by the following structural formula: where mean: C ₂ H ₄ OC ₂ H ₄ OR- a chlorine, bromine or fluorine atom or a cyano, nitro, trifluoromethyl, short-chain alkoxy, short-chain Alkoxyalkoxyalkanoyloxy, short-chain alkyl sulfonyl, arylsulfonyl, chlorarylsulfonyl, short-chain halogen-substituted alkylsulfonyl, short-chain alkoxycarbonyl, aroyl, aryloxysulfonyl or a short-chain alkanoyl radical; Ö $ Ö <m / 086S = 1, 2 or Τι; an acyl residue, R, R and R, which may have the same or different meanings, are each a hydrogen atom or a short-chain alkyl radical; a carbon atom or a short-chained alkyl, short-chain alkoxy or short-chain alkanoyloxy; R is a hydrogen atom, a short-chain alkyl or a short-chain alkoxy radical and R is a short-chain alkyl or cyclohexyl radical. 2. monoazo dyes according to claim 1, characterized by the following structural formula: CU. OC-H.OR "2 4 2 4 where mean: Y is a chlorine or bromine atom or a cyano radical; X is nitro or cyano; Λ a short-chain alkanoyl, benzoyl, short-chain alkoxycarbonyl, short-chain alkylsulfonyl or 030017/0865 Alkylcarbamoyl radical; R is a methyl radical or, if R or R is a water · substance atom, R is a short chain Alkyl radical; R ¹ and each represents a hydrogen atom or a methyl radical; \ l ^L and R ⁴ each a cassette atom and a short-chain alkyl radical. 3. monoazo dye according to claim 1, characterized by following formula: CH ₃ -C = O 4. monoazo dye according to claim 1, characterized by following formula: CH ₃ -C = O C ₂ H ₄ OClI ₂ H ₄ OC ₂ H ₅ 030017/0865 5. monoazo dye according to claim 1, characterized by following formula: LiN 0, N (/ VV-N = (CHJ 3'2 CH ₃ -C = OC ₂ II ₄ OCH ₂ H ₄ OC ₂ H ₅ 6. monoazo dye according to claim 1, characterized by following formula: CH ₃ -C = O C ₂ H ₄ OCH ₂ H ₄ OC ₂ Ii ₅ 7. monoazo dye according to claim 1, characterized by following formula: CH ₃ -C = O C ₂ H ₄ OCH ₂ H ₄ OC ₂ H ₅ 030017/0865 8. monoazo dye according to claim 1, characterized by the following formula: N = N CH ₃ CH ₂ CNH
0 9. monoazo dye according to claim 1, characterized by following formula: C ₂ II ₄ OCII ₂ H ₄ OC ₇ Ii ₅ 10. Use of monoazo dyes according to one of the claims 1 to 10 for dyeing textiles, especially made of polyesters. 030017/0865