GB2030166A - Dyestuffs - Google Patents

Abstract

Disperse monoazo dyestuffs having the general formula: <IMAGE> wherein R represents an optically substituted hydrocarbyl group, R<1> represents a hydrocarbyl group and Y represents an acyl group. The dyes are applicable to synthetic textile materials, e.g. cellulose acetates, 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 formula:

wherein R represents an optionally substituted hydrocarbyl group, R' represents a hydrocarbyl group and Y represents an acyl group.

The hydrocarbyl groups represented by R and R1 may be alkyl, alkenyl, cycloalkyl, aralkyl or aryl groups.

Examples of alkyl groups represented by R and R' are methyl, ethyl, n-propyl isopropyl, n-butyl and octyl.

An example of a cycloalkyl group represented by R and R1 is cyclohexyl.

Examples of aralkyl groups represented by R and R1 are benzyl and B-phenylethyl.

Examples of aryl groups represented by R and R7 are phenyl and tolyl.

Substituted hydrocarbyl groups which may be represented by R include substituted alkyl groups, for example chloro lower alkyl and lower alkoxy lower alkyl groups.

The acyl groups represented by Y include formyl, alkylcarbonyl, alkenylcarbonyl, arylcarbonyl, araikylcarbonyl, cycloalkylcarbonyl, alkylsulphonyl, arylsulphonyl, aminocarbonyl, alkylaminocarbonyl, alkoxycarbonyl and alkoxyalkoxycarbonyl groups. Examples of such groups include acetyl, propionyl, acryloyl, benzoyl, butyryl, hexanoyl, toluoyl, phenylacetyl, cyclohexylcarbonyl, methylsulphonyl, methoxycarbonyl, p-methoxyethoxycarbonyl and ethylaminocarbonyl. It is preferred that the various alkyl and alkoxy radicals present in the acyl groups are lower alkyl and lower alkoxy radicals.

It is preferred that the hydrocarbyl group represented by R is an alkyl group and especially a lower alkyl group.

It is also preferred that the alkyl and alkoxy radicals in the groups represented by Y are lower alkyl and lower alkoxy radicals, respectively.

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

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 arylamine having the formula:

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

wherein R, R1 and Y have the meanings stated above.

Examples of the arylamines of formula (II) which may be used in the process are methyl 2-amino-5nitrobenzoate, ethyl 2-amino-5-nitrobenzoate, butyl 2-amino-5-nitrobenzoate, octyl 2-amino-5- nitrobenzoate, cyclohexyl 2-amino-5-nitrobenzoate, benzyl 2-amino-5-nitrobenzoate and phenyl 2-amino-5- nitrobenzoate.

Examples of the coupling components of formula (III) which may be used are N-isopropyl-m- aminoacetanilide, N-methyl-m-aminoacetanilide, N-butyl-m-aminoacetanilide, N-octyl-m-aminoacetanilide, N-cyclohexyl-m-aminoacetanilide, N-benzyl-m-aminoacetanilide, N-B-phenylethyl-m-aminoacetanilide, Nphenyl-m-aminoacetanilide, N-ethyl-m-formylaminoaniline, N-ethyl-m-propionylaminoaniline, N-ethyl-mbutyrylaminoaniline, N-ethyl-m-hexanoylaminoaniline, N-ethyl-m-benzoylaminoaniline, N-ethyl-m-(2-, 3-or 4-toluoylamino)aniline, N-ethyi-m-[(phenylacetyl)amino]aniline, N-ethyl-mcyclohexylcarbonylaminoaniline, N-ethyl-m-(methylsulphonylamino)aniline, N-ethyl-mmethoxycarbonyla mino)aniline, N-ethyl-m-[(ss-methoxyethoxy)carbonyla mino]an iline, N-ethyl-m (aminocarbonylamino)aniline and N-ethyl-rn-(ethylaminocarbonylamino)aniline.

The diazotisation and coupling may be carried out by known 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 hydrochloric acid, sulphuric acid, an aqueous solution of sulphuric acid or a mixture of hydrochloric acid or 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 resulting 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 shades having good fastness to the tests conventionally applied to coloured synthetic textile materials, and in particular good fastness to sublimation (dry heat setting). They also have 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 Methyl 2-amino-5-nitrobenzoate (3.92 parts) is dissolved in a mixture of glacial acetic acid (40 parts) and concentrated hydrochloric acid (6 parts) and diazotised at 0-5"C by addition of 2N-aqueous sodium nitrite solution (10 parts). The solution of the diazonium compound so obtained is added to a mixture of N-isopropyl-m-aminoacetanilide (5.36 parts) in acetic acid (50 parts) and ice water (200 parts). The pH of the resulting mixture is adjusted to approximately 5 by the addition of sodium acetate, and after stirring for 2 hours the precipitated dyestuff is collected, washed with water and recrystallised from aqueous acetone.

When applied in the form of an aqueous dispersion to aromatic polyester textile material a bright bluish-red 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 amines listed in the third column.

The fourth column gives the shades obtained on aromatic polyestertextile material.

IExeple Diaoo Co ponent Corneent Coupling Co.ooont CouijlnpCo;poncnt CCOCN3 t2 Z < ç 2 ( E3)2 a YI-Ci2-CE(3)2 - 3 a "H 3::HCtl'CY3'r " 3 2 4 ,ua3%H5

4 ExWnple Diet, component Coupling Component I Shade 5 02N ,O1C3 uHPkN3 o2H2 \NECN(C2H5)2 No00CN3 6 sa 3 .. 7 t I 7 0 Y MHCH(C4H9)2 Example Diazo Component Coupling Component | Suede . -~ - 8 OzN 421l*3 S NHCIIze Red L 9 .. 0 , 3 10 . \)) NHC8Hr7 Hluiai red Enmple ' Diezo Component Coupling Coopoocat | "node ImMI, 11 02NX(223 \ < DLt Red I "H3 NH,,C,3 12 Bloiofl Th-, red 13 RHffi03 lelloi,o NH OdIt

'Hempie nLezo Component Coupling Coo,oonaflt Shade '4 NHCHO 14 0 a RH - c25 red Hiujet "H NHCOC N 19 HH - CN - C2H9 "H3 Kac3 16 (NH 4- CH3 013 Exantple Mao Component Coupling Coeponeat i Horde aXMCH3 N W"'HCN I 17 oH\n( 5'\2 - Hluiah I 32 red 18 j j RHOOCO 19 (SIrSCH(CE3)Z Z-mple / Ciozo Component Coupling Coononeat 1 shave CCO5E3 NOCOCCi 20 Ni - "H - C H5 Hlui,a 3 1 I H 1"9 -Th-Ci("H) 2t I 2 22 / "tHccLJi5' I 22 252

sample fliazo Component Coupling Component | 2haze =. ~ . CODCH3 2 5 23 2 t NH2 IBluish ~ red I - I 211 C2H5 013 NHCDC4Cl 29 " NH011-C,dH5 C83 Exalople Diazo Compon2nt Conoling Ceaponeat COCCE3 NHa)la=(32 26 OzN4NHz 4,3 NH - "H - C2H5 I ma 013 NHCOCH 27 NH"H2C = "Ha Ned 27 " 0000 25 NHCOCH 28 OzNolZ NH 9 "H - C2 HluiL l CH Romeole Otazo Component Coupling Component ) shade 00001(0') NHCO01 29 = DO(5H,)2 Hlui - red 013 000C 29 3O 2 < a &num;6 - CDoC17 31 2 021 2 0 0 32 6 *.

Rpie Diaw Component Coopluog Component shade COOC H Cl NHCOCFE 33 CaN 4 12 C 3 Bluis'a 3 000C2N40013 3 2 2 e s - - 000012012 NHOOe 3 " ORR'ia NH01(013)2 I. omple Diau, Conponont I Coupling Cotlpe~es~ shade ODOCE2t rucocH3 36 O N9 (/ S NHe (CE3)2 BreldiEh~ CDO {03 . l 37 02ff4 =2 n C I 38 02NX.NHe .w *. | 2 example Diaw Component Coupling Cnpeilent I shade C004 3 39 02N4NH2 SlHeE(C2H5)2 | Red NH502 40 b~NHCE(CE3)2 " NdCOOH3 W ~ . t\L hHC2E5 f , NHC2uS red

Claims (10)

1. A disperse monoazo dyestuff having the general formula:

wherein R represents an optionally substituted hydrocarbyl group, R1 represents a hydrocarbyl group and Y represents an acyl group.

2. A disperse monoazo dyestuff as claimed in claim 1 wherein R is an alkyl group.

3. A disperse monoazo dyestuff as claimed in claim 1 wherein R is a lower alkyl group.

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

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

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

wherein R, R1 and Y have the meanings stated in claim 1.

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

7. A disperse monoazo dyestuff whenever manufactured by a method claimed in claim 5 or claim 6.

8. 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 4 and 7.

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

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