GB2030590A

GB2030590A - Dyestuffs

Info

Publication number: GB2030590A
Application number: GB7927351A
Authority: GB
Original assignee: Imperial Chemical Industries Ltd
Current assignee: Imperial Chemical Industries Ltd
Priority date: 1978-09-08
Filing date: 1979-08-06
Publication date: 1980-04-10

Abstract

Disperse monoazo dyestuffs have the formula: <IMAGE> wherein R represents alkyl or a group of the formula: <IMAGE> or <IMAGE> in which R<1> represents alkyl, R<2> represents aryl, R<3> represents hydrogen or alkyl and n is a positive integer; X represents hydrogen or nitro; Y represents hydrogen, halogen or alkyl; and Z represents hydrogen, C1-6 alkyl or alkoxy. The dyes are applicable to synthetic textile materials, acetates, cellulose polyamides and especially aromatic polyester textile materials.

Description

SPECIFICATION Dyestuffs This invention relates to dyestuffs and more particularly to disperse monoazo dyestuffs based on secondary amine coupling components.

According to the present invention there are provided disperse monoazo dyestuffs having the general formola:

wherein R represents alkyl our a group of the formula:

in which R1 represents alkyl, R2 represents aryl, R3 represents hydrogen or alkyl and n is a positive integer; X represents hydrogen or nitro; Y represents hydrogen, halogen or alkyl; and Z represents hydrogen,-C1~6 alkyl or alkoxy.

It is preferred that the alkyl groups represented by R, R1, R3 and Y are lower alkyl groups and that the alkoxy groups represented by Z are lower alkoxy groups.

In this specification the terms "lower alkyl" and "lower alkoxy" mean alkyl and alkoxy groups respectively which contain from 1 to 4 carbon atoms.

Examples of the alkyl groups represented by R, R1, R3 and Y are methyl, ethyl, n-propyl, isopropyl and n-butyl.

Examples of the' alkoxy groups represented by Z are methoxy and ethoxy.

Examples of the halogen atoms represented by Y are chlorine and bromine atoms.

Examples of the alkyl groups represented by Z are, in addition to lower alkyl groups, the n-pentyl group and n-hexyl group.

According to a further feature of the invention there is provided a process for the manufacture of disperse monoazo dyestuffs having the above defined formula (I) which comprises diazotising an aryl amine having the formula:

and coupling the diazonium compound so obtained on to a coupling component having the formula:

wherein R, X, Y and Z have the meanings stated above.

The arylamine of formula (II) may be 2-cyano-4-nitro-aniline or 2-cyano-4,6-dinitroaniline.

Examples of the coupling components of formula (Ill) which may be used are N-isopropyl-m aminoacetanilide, N-( 1 -ethylpropyl)-m-aminoacetanilide, N-methyl-m-aminoacetanilide, N-n-butyl-rn- aminoacetanilide, N-octyl-m-aminoacetanilide, N-benzyl-m-aminoacetanilide, N-(p-phenylethyl)-m- a minoacetanilide, N-ethyl-m-formyla minoa ni li ne, N-ethyl-m-propionyla mi noanil ine, N-ethyl-m butyrylaminoaniline, N-ethyl-m-hexanoyla minoa niline, N-ethyl-m-methoxycarbonylaminoaniline, N ethyl-m-ethoxyca rbonyla minoaniline, N-ethyl-m-(P-m ethoxyethoxycarbonyla mino)a niline, 2-methyl-5 acetylamino-N-isobutylaniline and 2-chloro-5-acetylamino-N-isobutylaniline.

The diazotisation and coupling may be carried out by know methods for these reactions. For example, the process may be carried out by adding sodium nitrite to a solution or dispersion of the arylamine in sulphuric acid, an aqueous solution thereof or a mixture of sulphuric acid with an organic acid such as acetic and/or propionic acid, or by stirring the arylamine with nitrosylsulphuric acid, followed by addition of the resuiting solution or dispersion of the diazonium compound thus obtained to a solution of the coupling component in water or in a mixture of water and a water-miscible organic liquid, if necessary adjusting the pH of the mixture to facilitate the coupling reaction, and finally isolating the resulting dyestuff by conventional methods.

According to a yet further feature of the invention there is provided a method for the colouration of synthetic textile materials which comprises applying to the said synthetic textile materials from an aqueous medium a monoazo dyestuff as hereinbefore defined.

The dyestuffs of the present invention may be applied to synthetic textile materials by dyeing, padding or printing methods in the form of aqueous dispersions which are prepared by conventional methods, for example, by milling the dyestuffs with water and a suitable dispersing agent such as the sodium salt of a naphthalene-2-sulphonic acid/formaldehyde condensate.

Examples of synthetic textile materials to which the dyestuffs may be applied are textile materials fabricated from secondary cellulose acetate, cellulose triacetate, polyamides such as poly(hexamethylene adipamide) and above all aromatic polyesters such as polyethylene terephthalate.

The dyestuffs may also be applied to synthetic textile materials by known methods of transfer colour printing such as sublimation transfer printing, optionally under reduced pressure, and wet transfer printing.

The dyestuffs also find application for the melt colouration of polymers such as aromatic polyesters.

When applied to synthetic textile materials as indicated above, the dyestuffs of the present invention provide bright bluish-red to red-violet shades having good fastness to the tests conventionally applied to coloured synthetic textile materials, and in particular good dyeing properties and tinctorial strength.

The invention is illustrated but not limited by the following Examples in which parts and percentages are by weight.

Example 1 2-Cyano-4-nitroaniline (3.26 parts) is dissolved at 0--5 OC in concentrated sulphuric acid (30 parts) containing sodium nitrite (1.38 parts) and stirred atO-50C for 2 hours. The diazonium solution so obtained is added to a solution of N-isopropyl-m-aminoacetanilide (5.36 parts) in acetic acid (50 parts) and ice water (200 parts). The pH of the mixture is adjusted to approximately 5 with sodium acetate and the mixture is stirred for 2 hours. The precipitated dyestuff is filtered off, washed with water and dried.

When applied in the form of an aqueous dispersion to aromatic polyester textile material a redviolet shade is obtained.

The following table gives further Examples of dyes of the invention which may be obtained by diazotising the amines listed in the second column and coupling with the secondary arylamines listed in the third column. The shades obtained on aromatic polyester textile material are given in the fourth column.

t ii o a NO2 pGr( 3 U mN 8 I=Q blue | 4X d t1 b 8 N

: :xple Diazo Component Couplin Component shade CN a v H 02N NO2 - CH as II NHCO3 'I P1 Q, - as cH3 7 1I NHCOaL3 Reddi violet t3 &commat; P: | C= A Si ~

S I o Q o d +1 O P P aO 8 02N XP Rubine NO2 9 It NECOCH Reddi 3 violet NHC2H5 d It NHCOCH3 II I E4 NHCH aH W C H 21 25 CH3 &num; N S C n N O | X O g

example Diazo Component Coupling Component Shade o K p s X 11 &num; &num; NO2 ia It NH00aH3 Rubine H Cl 13 II tilo 8Eg NH - IdaO violet t t | 8t L i b v fU 14

t i Component Coupling Component Shade o NHCOCH3 t oce Orl - PGP CR 3 15 II NHCOOC2H Reddish blue h +r ig v 16 It u\ BI n WN Wcu I 9 Se e 8 9 N u o

I CN g i g i Ap u In 25 CR 18 II bc(u II - C H CR 3 tio ig,i4 w - C H - i as CR3 ~~~ 49 B oN A b X > X l

O KiP vl Diazo Component Coupling Component shade CN 3 20 %NNH2 )NH .CH - C H5 Rveidodieitsh f a CR3 21 tI NECOOC H II 4 u cu H S O N

Claims

1. A disperse monoazo dyestuff having the general formula:

wherein R represents alkyl or a group of the formula:

in which R1 represents alkyl, R2 represents aryl, R3 represents hydrogen oralkyl and n is a positive integer; X represents hydrogen or nitro; Y represents hydrogen, halogen or alkyl; and Z represents hydrogen, C16 alkyl or alkoxy.

2. A disperse monoazo dyestuff as claimed in claim 1 wherein any alkyl groups represented by R, R1, R3orYare loweralkyl groups.

3. A disperse monoazo dyestuff as claimed in claim 1 and specifically identified herein.

4. A process for the manufacture of a disperse monoazo dyestuff as defined in claim 1 which comprises diazotising an aryl amine having the formula:

and coupling the diazonium compound so obtained with a secondary amine having the formula:

wherein X, Y, Z and R have the meanings given in claim 1.

5. A process as claimed in claim 4 conducted substantially as hereinbefore described with reference to any one of the foregoing Examples.

6. A disperse monoazo dyestuff whenever manufactured by a process claimed in claim 4 or claim 5.

7. A process for the coloration of synthetic textile materials which comprises applying thereto a disperse monoazo dyestuff as claimed in any one of claims 1 to 3 and 6.

8. A process as claimed in claim 7 wherein the synthetic textile material is an aromatic polyester textile material.

9. Synthetic textile materials whenever coloured by the process claimed in claim 7 or claim 8.