DESC:FIELD OF INVENTION
The present invention relates to novel disperse azo dyes and its use in colouration of fibers. The present invention more particularly relates to colouration of Polyester fibers including Polyester-elastane blends, Lycra blends, and Polyamide fibers by conventional methods as well as Supercritical fluid dyeing technology. Disperse azo dyes of present invention have excellent fastness properties.

BACKGROUND OF THE INVENTION AND PRIOR ART
Traditionally, disperse dyes are used for dyeing synthetic fibers and its blend with other fibers such as cellulose, polyurethane, nylon and wool by usual exhaust dyeing, continuous dyeing and printing techniques.

Indian Patent number: IN 190551 (1700/DEL/94) which is the Indian equivalent of WO950200014 relates to a process for colouring synthetic textile materials using azo dyes, to a process for the mass coloration of plastics, to plastics when coloured, to certain novel azo dyes and to compositions containing azo dyes.

DE2557523 discloses ß-Anilinoethanesulfonylfluoride dyes and its use for the manufacture of dyes. It also disclosed a process for the preparation of dyes, using ß-Anilinoethanesulfonylfluoride. Dyes were applied to polyester fabrics using Heat Fixing Process and studied for Light fastness, Sublimation fastness and migration properties. This patent did not mention anything related to dyes behavior in exhaust dyeing. Moreover, it also did not provide any study on dyes property with respect to washing fastness and staining to different fabrics.

WO2011077462 is directed to disperse azo dye of formula (I) with good fastness properties with at least one sulfonylfluoride substituent and one ester substituent. This patent specifically disclosed dyes comprising of one sulfonylfluoride group and further fastness properties of these dyestuffs and more particularly improvement on sublimation and washing fastness properties on polyester.
Recently with changing trends, fashion and market requirement consumption of blended fabrics is significantly increased. These new fabrics are made out of micro size fiber using fine denier polyester fiber or Lycra blends or blending fiber with polyurethane, nylon and wool. The fastness properties of these new colored fabrics become worse with respect to light fastness and sublimation fastness, particularly washing fastness when dyed or printed with conventional disperse dyes.

Indian Patent application: 3577/MUM/2015 relates to a method for dyeing polyamide/nylon, silk, wool, polyester and blends of these fibers with fiber reactive disperse dyestuffs in a supercritical carbon dioxide.

To overcome limitations of fastness in synthetic textiles due to disperse azo dyes, as also to achieve efficient dyeing through supercritical fluid technology, the inventors of the present invention have developed range of disperse azo dyes with excellent overall fastness properties. Further these dye products having more than one sulfonyl fluoride groups in dyes molecule also help to provide better solution for colouration of different fibers and their blends with excellent fastness properties using conventional dyeing technology as well as supercritical fluid dyeing technology.

OBJECT OF INVENTION
It is an object of the present invention to provide disperse azo dyes.

It is a further object of the present invention to provide disperse azo dyes that have excellent fastness on the polyester, Polyester-elastane blends and polyamide fibers inclusive of Lycra and other blends.

It is another object of the present invention to provide a process for colouration of synthetic textile materials using conventional methods of dyeing.

It is another object of the invention to provide an environmental friendly process for dyeing synthetic textile materials with disperse azo dyestuffs.

It is another object of the present invention to provide an environmental friendly process for colouration of synthetic textile materials using SCF dyeing technology.

It is another object of the invention to provide an environmental friendly method for dyeing polyester/ Polyester-elastane blends/polyamide/Lycra and other blend fibers with disperse azo dyestuffs using SCF dyeing technology.

SUMMARY OF THE INVENTION
According to one aspect of the present invention there is provided Disperse azo Dyes of formula (1),

wherein dye molecule of formula (I) comprises of at least two SO2F groups either as substituent, sub-substituent or combination thereof;
X, Y and Z are, independently, hydrogen, methyl, halogen, cyano, nitro or -SO2F, wherein at least one of X, Y and Z is SO2F;
R1 is hydrogen, methyl, hydroxyl or -NHR5;
R5 is -COCH3, -COC2H5, -SO2CH3, -SO2C2H5;
R2 is hydrogen, chloro or methoxy;
R3 and R4 are independently (C1-C4)-alkyl, -CH2CH2CN; –CH2CH2OCOR6, –CH2CH2COOR7, or –CH2CH2SO2R8;
R6 is –OH, C1-C4 alkyl, and
R7 is Hydrogen, C1-C4 alkyl, -CH2CH2CN; -CH2COCH3; -CH2COOCH3;
R8 is Cl or F
wherein R3 and R4 bear alkyl substituents only when at least two substituents from X, Y and Z bears SO2F substituent;
wherein when Y & Z both are Cl, R1 is other than methyl.

Disperse dyes defined in the Formula (1) have excellent washing fastness and light fastness on the synthetic fibers such as polyester and polyamide fibers inclusive of Lycra and other blends.

DETAILED DESCRIPTION OF THE PRESENT INVENTION
Disperse azo dyes are generally prepared by diazotization of primary aromatic amine and subsequently coupled with suitable coupling component.

The present invention relates to disperse azo dyes and methods for applying these dyes to fibers by conventional as well as SCF dyeing technology.

The disperse azo dyes are used for dyeing polyester and its blends with other fibers such as cellulose, polyurethane, wool and polyamide fibers by usual exhaust dyeing, continuous dyeing, SCF dyeing and printing techniques. The fastness properties of some colored fibers become worse in light fastness, sublimation fastness and particularly washing fastness, due to use of finer size denier polyester fiber or blending fiber with polyurethane, nylon and wool. The excellent dyestuff to endure this use is desired in this dyeing and printing field.

To solve these problems, the inventors of the present invention have engineered disperse azo dyestuffs with excellent fastness properties, which are showed as formula (1)

wherein dye molecule of formula (I) comprises of at least two SO2F groups either as substituent, sub-substituent or combination thereof;
X, Y and Z are, independently, hydrogen, methyl, halogen, cyano, nitro or -SO2F, wherein at least one of X, Y and Z is SO2F;
R1 is hydrogen, methyl, hydroxyl or -NHR5;
R5 is -COCH3, -COC2H5, -SO2CH3, -SO2C2H5;
R2 is hydrogen, chloro or methoxy;
R3 and R4 are independently (C1-C4)-alkyl, -CH2CH2CN; –CH2CH2OCOR6, –CH2CH2COOR7, or –CH2CH2SO2R8;
R6 is –OH, C1-C4 alkyl, and
R7 is Hydrogen, C1-C4 alkyl, -CH2CH2CN; -CH2COCH3; -CH2COOCH3;
R8 is Cl or F
wherein R3 and R4 bear alkyl substituents only when at least two substituents from X, Y and Z bears SO2F substituent;
wherein when Y & Z both are Cl, R1 is other than methyl.

In the present application, the term “substitution” refers to substituents which are directly attached to the formula described therein.

In the present application, the term “sub-substitution” refers to such substituents which are further attached to the substituents directly attached to the formula described therein.

Under appropriate conditions, primary aromatic amine can be successfully diazotized and coupled with specially developed coupling component to get novel disperse dyes of formula (1). These new disperse dyes possesses excellent washing and light fastness properties.

Examples:
The present invention is concretely explained as follows, but the present invention is not limited in these examples.
Example-1:
Structural formula (2)

Formula (2)
Example 1 of structural formula (2) is synthesized by following method:
4-Amino benzenesulfonyl fluoride 3.5 g is dissolved in 10 g of Hydrochloric acid and cooled to 0-5 ºC with ice and add solution of 1.45 g NaNO2 dissolved in 5 ml water and stir reaction mass to complete diazotization at 0-5 ºC for 2 hrs. Coupler, 3-Methyl-N:Ethyl-N’-Ethylsulfonylfluoride aniline 5.1 g is dissolved in dilute HCl 100 ml and the synthesized diazo solution is added into this coupler solution at 0-5 ºC. The reaction mass is stirred for 1hr below 5ºC and filtered the crystal solid and washed with water till neutral washing. Wet press cake is collected and dried at 60 ºC to get 7.7 g of dry dye of formula-2 having M.P. 154-156 ºC and ?max in acetone of dyestuff is 469 nm.

Example-2:
Structural formula (3)

Formula (3)
Example 2 of structural formula (3) is synthesized by following method:
40% nitrosyl sulfuric acid 3 ml is added to the mixture of 2:4-disulfonylfluoride aniline 2.0 g and 12 g of sulfuric acid at 0-5 ºC and stirred for 1 hrs below 5ºC. Coupler, 3-N:N’-Diethylamino acetanilide 1.75 g is dissolved in dilute HCl 100 ml and the synthesized diazo solution is added into this coupler solution at 0-5ºC. The reaction mass is stirred for 1hr below 5ºC and further diluted with ice water and filter the crystal solid and washed with water.
The wet cake is dried to get 3.5 g of dyestuff of formula (3) having M.P. 152-154 ºC and ?max in acetone is 504 nm.

Example-3:
Structural formula (4)

Formula (4)
Example 3 of structural formula (4) is synthesized by following method:
40% nitrosyl sulfuric acid 3 ml is added to the mixture of 2:4-disulfonylfluoride aniline 2.0 g and 12 g of sulfuric acid at 0-5 ºC and stirred for 1 hrs below 5ºC. Coupler, 4-Methoxy-3-N:N’-Diallylamino acetanilide 2.1 g is dissolved in dilute HCl 100 ml and the synthesized diazo solution is added into this coupler solution at 0-5 ºC. The reaction mass is stirred for 1hr below 5ºC and further diluted with ice water and filter the crystal solid and washed with water.
The wet cake is dried to get 3.55 g of dyestuff of formula (4) having M.P. 168-170 ºC and ?max in acetone is 596 nm.

Example-4:
Structural formula (5)

Formula (5)
Example 4 of structural formula (5) is synthesized by following method:
40% nitrosyl sulfuric acid 3 ml is added to the mixture of 2:4-disulfonylfluoride aniline 2.0 g and 12 g of sulfuric acid at 0-5 ºC and stirred for 1 hrs below 5ºC. Coupler, 4-Methoxy-3-N:N’-Diacetoxyethylamino acetanilide 2.9 g is dissolved in dilute HCl 100 ml and the synthesized diazo solution is added into this coupler solution at 0-5 ºC. The reaction mass is stirred for 1hr below 5ºC and further diluted with ice water and filter the crystal solid and washed with water.
The wet cake is dried to get 4.4 g of dyestuff of formula (5) having M.P. 120-122 ºC and ?max in acetone is 590 nm.

Example-5:
Structural formula (6)

Formula (6)
Example 5 of structural formula (6) is synthesized by following method:
40% nitrosyl sulfuric acid 3 ml is added to the mixture of 2:5-dichlorofluorosulfonyl aniline 2.0 g, acetic acid and propionic acid (86:14, 25ml) at 0-5 ºC and stirred for 2 hrs below 5ºC. Coupler, 3-Nethyl-N’-ethylsulfonyl fluoride aniline 1.9 g is dissolved in dilute HCl 100 ml and the synthesized diazotized solution is added into this coupler solution at 0-5 ºC. The reaction mass is stirred for 1hr below 5ºC and filtered the crystal solid and washed with water. Wet cake is dried at 60 ºC to get 3.5 g dyestuff of formula (6) having M.P. 162-164 ºC and ?max 490 nm in acetone.

Example-6:
Structural formula (7)

Formula (7)
Example 6 of structural formula (7) is synthesized by following method:
40% nitrosyl sulfuric acid 3 ml is added to the mixture of 2:4-disulfonylfluoride aniline 2.0 g and 12 g of sulfuric acid at 0-5 ºC and stirred for 1 hrs below 5ºC. Coupler, N:Ethyl-N’-Ethylsulfonylfluoride aniline 1.85 g is dissolved in dilute HCl 100 ml and the synthesized diazo solution is added into this coupler solution at 0-5 ºC. The reaction mass is stirred for 1hr below 5ºC and further diluted with ice water and filter the crystal solid and washed with water.
The wet cake is dried to get 3.5 g of dyestuff of formula (7) having M.P. 152-154 ºC and ?max in acetone is 489 nm.

Example-7:
Structural formula (8)

Formula (8)
Example 2 of structural formula (3) is synthesized by following method:
40% nitrosyl sulfuric acid 3 ml is added to the mixture of 2:4-disulfonylfluoride aniline 2.0 g and 12 g of sulfuric acid at 0-5 ºC and stirred for 1 hrs below 5ºC. Coupler, N-Ethyl--N’-Ethylsulfonylfluoride acetanilide 2.4 g is dissolved in dilute HCl 100 ml and the synthesized diazo solution is added into this coupler solution at 0-5 ºC. The reaction mass is stirred for 1hr below 5ºC and further diluted with ice water and filter the crystal solid and washed with water.
The wet cake is dried to get 4 g of dyestuff of formula (8) having M.P. 180-182 ºC and ?max in acetone is 494 nm.

Further dyestuffs of formula (9) are as provided in the below table.

Formula(9)
wherein,
Example Y Z R1 R2 R3 R4
8 H SO2F NHR5 H C2H4CN C2H5
9 H SO2F NHR5 H C2H4CN C2H4CN
10 H SO2F NHR5 -OCH3 C2H4CN C2H5
11 H SO2F NHR5 -OCH3 C2H4CN C2H4CN
12 CH3 SO2F NHR5 H C2H4CN C2H5
13 CH3 SO2F NHR5 H C2H4CN C2H4CN
14 CH3 SO2F NHR5 -OCH3 C2H4CN C2H5
15 CH3 SO2F NHR5 -OCH3 C2H4CN C2H4CN
16 Cl SO2F NHR5 H C2H4CN C2H5
17 Cl SO2F NHR5 H C2H4CN C2H4CN
18 Cl SO2F NHR5 -OCH3 C2H4CN C2H5
19 Cl SO2F NHR5 H C2H4CN C2H5
20 CH3 SO2F NHR5 H C2H5 C2H5
21 CH3 SO2F NHR5 H CH2CHCH2 CH2CHCH2
22 CH3 SO2F NHR5 -OCH3 C2H5 C2H5
23 CH3 SO2F NHR5 -OCH3 CH2CHCH2 CH2CHCH2
24 Cl SO2F NHR5 H C2H5 C2H5
25 Cl SO2F NHR5 H CH2CHCH2 CH2CHCH2
26 Cl SO2F NHR5 -OCH3 C2H5 C2H5
27 Cl SO2F NHR5 H CH2CHCH2 CH2CHCH2
28 NO2 SO2F NHR5 H C2H5 C2H5
29 NO2 SO2F NHR5 H C2H4CN C2H5
30 NO2 SO2F NHR5 -OCH3 C2H5 C2H5
31 NO2 SO2F NHR5 H C2H4CN C2H5
32 CN SO2F NHR5 H C2H5 C2H5
33 CN SO2F NHR5 H C2H4CN C2H5
34 CN SO2F NHR5 -OCH3 C2H5 C2H5
35 CN SO2F NHR5 H C2H4CN C2H5
36 NO2 SO2F Cl H C2H5 C2H5
37 CN SO2F Cl H C2H5 C2H5
38 NO2 SO2F OH H C2H5 C2H5
39 Cl SO2F OH H C2H5 C2H5
40 Cl SO2F NHR5 H C2H4COOCH2COOCH3 C2H4COOCH2COOCH3
41 Cl SO2F NHR5 H C2H4COOCH2COCH3 C2H4COOCH2COCH3
42 Cl SO2F CH3 H C2H4SO2F C2H5
43 NO2 SO2F CH3 H C2H4SO2F C2H5
44 NO2 SO2F CH3 H C2H4SO2F C2H5
R5 substituent in above table is either –COCH3, -COC2H5.

Dyestuffs of Formula (9) are prepared by general method of synthesis as below:
40% nitrosyl sulfuric acid 3 ml is added to the mixture of 0.02 moles Amines and 12 g of sulfuric acid at 0-5 ºC and stirred for 1 hrs below 5ºC. 0.021moles Coupler is dissolved in dilute HCl 100 ml and the synthesized diazo solution is added into this coupler solution at 0-5 ºC. The reaction mass is stirred for 1hr below 5ºC and further diluted with ice water and filter the crystal solid and washed with water. The wet cake is dried to get 85-90% yield of dyestuff of formula (9).

The wet press cake prepared by the above processes is further used in four different dyeing methods,
1. Conventional Exhaust Dyeing of Polyester
2.0 g of the obtained wet press cake is milled with 2.0g of naphthalenesulfonic acid-formaldehyde condensate and 50g of water and 500 g of glass beads (average side is 0.8mm of diameter.) for 24 hr and after milling, the mass is filtered to separate glass beads.
The 20g of the obtained finished liquid is added in the 100 ml of water and kept the pH 4 with acetic acid, and 10g piece of polyester is added into the dye bath for exhaust dyeing.
The dyeing bath is heated to 135 ºC and kept for 40min. After proper rinsing, washing and drying, the dyed material is evaluated for reflectance, washing fastness, lightfastness and sublimation fastness.

2. Dyeing of Polyester with Super Critical Fluid (CO2)
Laboratory Dyeing of polyester fabrics with super critical fluid (CO2) comprises the steps of placing dyes up to 2% of the weight of polyester fabric and 10 gms of polyester fabric in dyeing pot depending upon the shade requirement. Close the dyeing pot tightly, Purging desired quantity of Liquid CO2 to this tightly closed dyeing pot; subjecting it to dyeing cycle at 120°C and 250 bar pressure for 90 minutes. After proper rinsing, washing and drying, the dyed material is evaluated for reflectance, washing fastness, lightfastness and sublimation fastness.

3. Conventional dyeing of polyamide
The 0.2g of dye powder added in the 250 ml of water and kept the pH 4 and 10g piece of polyamide is added into the dye bath for exhaust dyeing. The dyeing bath is heated to 98 ºC and kept for 60 min. After proper rinsing, washing and drying, the dyed material is evaluated for reflectance, washing fastness, light fastness and sublimation fastness.

4. Dyeing with Super Critical Fluid (CO2) of Polyamide
Laboratory Dyeing of polyester fabrics with super critical fluid (CO2) comprises the steps of placing dyes of formula-I (up to 2% of the weight of polyester fabric) and 10 gms of polyamide fabric in dyeing pot. Close the dyeing pot tightly, Purging desired quantity of Liquid CO2 to this tightly closed dyeing pot; subjecting it to dyeing cycle at 120°C and 250 bar pressure for 90 minutes. After proper rinsing, washing and drying, the dyed material is evaluated for reflectance, washing fastness, lightfastness and sublimation fastness.

To confirm fixation on polyamide, dyed polyamide fabric using carbon dioxide is subjected to after treatment with Acetone, Ethanol: Acetic acid (1:1 mixture) and even with DMF and in all very little dye get removed in washing.

All above differently dyed fabrics were evaluated for Reflectance Spectra for colour measurements and Fastness properties using following test methods, Washing Fastness as per Test Method AATCC 61 2A, Light Fastness as per Test Method ISO 105 B02 and Sublimation Test at 180 deg for 30 sec and at 210 deg for 30 sec.

DYE Fabric Washing Fastness Light Fastness Sublimation Fastness @ 180°C
AC CO PA PES
Formula-2 PES 5 5 5 5 3-4 5
PES/EL 4-5 5 5 5 3 3
PA 4 3-4 3-4 4 4-5 4-5
Formula-3 PES 5 5 5 5 3-4 3-4
PES/EL 5 5 5 5 3 3-4
PA 4-5 4 4 4-5 4-5 4-5
Formula-4 PES 5 5 5 5 3-4 4
PES/EL 5 5 5 5 3 3-4
PA 4-5 4 4 4-5 4 4
Formula-5 PES 5 5 5 5 3-4 4
PES/EL 5 5 5 5 3-4 4-5
PA 4-5 4 4 4-5 4 5
Formula-6 PES 5 5 5 5 4 3-4
PES/EL 5 5 5 5 4 3-4
PA 4-5 4 4 4-5 4-5 4
Formula-7 PES 5 5 5 5 4-5 3-4
PES/EL 4-5 4-5 4-5 4-5 4 3-4
PA 4-5 4-5 4-5 4-5 4-5 4-5
Formula-8 PES 5 5 5 5 4 4
PES/EL 5 5 5 5 4 4
PA 4 3-4 3-4 4-5 4 4

PES-Polyester, PES/EL is Polyester Elastane blend, PA is Polyamide, AC is Cellulose Acetate and CO is Cotton.
,CLAIMS:1. Disperse azo dyes of formula (1)

wherein the dye molecule of formula (I) comprises at least two SO2F groups either as substituent, sub-substituent or combination thereof;
X, Y and Z are, independently, hydrogen, methyl, halogen, cyano, nitro or SO2F, wherein at least one of X, Y and Z is SO2F;
R1 is hydrogen, methyl, hydroxyl or NHR5;
R5 is COCH3, COC2H5, SO2CH3, SO2C2H5;
R2 is hydrogen, chloro or methoxy;
R3 and R4 are independently selected from (C1-C4) alkyl, -CH2CH2CN; -CH2CH2OCOR6, -CH2CH2COOR7, or –CH2CH2SO2R8;
R6 is –OH, C1-C4 alkyl;
R7 is Hydrogen, C1-C4 alkyl, -CH2CH2CN, -CH2COCH3, -CH2COOCH3;
R8 is Cl or F;
wherein R3 and R4 bear (C1-C4) alkyl substituents only when at least two substituents from X, Y and Z bears SO2F substituent;
wherein when Y & Z are both are Cl, R1 is other than methyl.

2. Disperse azo dyes as claimed in claim 1 in which the compound of formula (1) is of formula (2):

Formula (2)

3. Disperse azo dyes as claimed in claim 1 in which the compound of formula (1) is of formula (3):

Formula (3)

4. Disperse azo dyes as claimed in claim 1 in which the compound of formula (1) is of formula (4):
Formula (4)

5. Disperse azo dyes as claimed in claim 1 in which the compound of formula (1) is of formula (5):

Formula (5)

6. Disperse azo dyes as claimed in claim 1 in which the compound of formula (1) is of formula (6):

Formula (6)

7. Disperse azo dyes as claimed in claim 1 in which the compound of formula (1) is of formula (7):

Formula (7)

8. Disperse azo dyes as claimed in claim 1 in which the compound of formula (1) is of formula (8):

Formula (8)

9. Disperse azo dyes as claimed in claim 1 in which the compound of formula (1) is of formula (9)

Formula(9)
wherein,
Example Y Z R1 R2 R3 R4
8 H SO2F NHR5 H C2H4CN C2H5
9 H SO2F NHR5 H C2H4CN C2H4CN
10 H SO2F NHR5 -OCH3 C2H4CN C2H5
11 H SO2F NHR5 -OCH3 C2H4CN C2H4CN
12 CH3 SO2F NHR5 H C2H4CN C2H5
13 CH3 SO2F NHR5 H C2H4CN C2H4CN
14 CH3 SO2F NHR5 -OCH3 C2H4CN C2H5
15 CH3 SO2F NHR5 -OCH3 C2H4CN C2H4CN
16 Cl SO2F NHR5 H C2H4CN C2H5
17 Cl SO2F NHR5 H C2H4CN C2H4CN
18 Cl SO2F NHR5 -OCH3 C2H4CN C2H5
19 Cl SO2F NHR5 H C2H4CN C2H5
20 CH3 SO2F NHR5 H C2H5 C2H5
21 CH3 SO2F NHR5 H CH2CHCH2 CH2CHCH2
22 CH3 SO2F NHR5 -OCH3 C2H5 C2H5
23 CH3 SO2F NHR5 -OCH3 CH2CHCH2 CH2CHCH2
24 Cl SO2F NHR5 H C2H5 C2H5
25 Cl SO2F NHR5 H CH2CHCH2 CH2CHCH2
26 Cl SO2F NHR5 -OCH3 C2H5 C2H5
27 Cl SO2F NHR5 H CH2CHCH2 CH2CHCH2
28 NO2 SO2F NHR5 H C2H5 C2H5
29 NO2 SO2F NHR5 H C2H4CN C2H5
30 NO2 SO2F NHR5 -OCH3 C2H5 C2H5
31 NO2 SO2F NHR5 H C2H4CN C2H5
32 CN SO2F NHR5 H C2H5 C2H5
33 CN SO2F NHR5 H C2H4CN C2H5
34 CN SO2F NHR5 -OCH3 C2H5 C2H5
35 CN SO2F NHR5 H C2H4CN C2H5
36 NO2 SO2F Cl H C2H5 C2H5
37 CN SO2F Cl H C2H5 C2H5
38 NO2 SO2F OH H C2H5 C2H5
39 Cl SO2F OH H C2H5 C2H5
40 Cl SO2F NHR5 H C2H4COOCH2COOCH3 C2H4COOCH2COOCH3
41 Cl SO2F NHR5 H C2H4COOCH2COCH3 C2H4COOCH2COCH3
42 Cl SO2F CH3 H C2H4SO2F C2H5
43 NO2 SO2F CH3 H C2H4SO2F C2H5
44 NO2 SO2F CH3 H C2H4SO2F C2H5
wherein R5 is either –COCH3, -COC2H5.

10. A process for dyeing and printing fiber materials which comprises treating the fiber materials with a dye of the formula (1) to formula (9) as claimed in any one of the preceding claims.

11. The process as claimed in claim 10, wherein the fiber material is selected from synthetic fibers such as polyester, Polyester-elastane blends, polyamide, Lycra and other blend fibers.