FORM2
THE PATENTS ACT, 1970
(39 of 1970)
&
The Patents Rules, 2003
COMPLETE SPECIFICATION
(See section 10; rule 13)
Title of the invention - "YELLOW DISPERSE DYE AND THE DISPERSE DYE
MIXTURES"
2. Applicant(s)
(a) NAME : COLOURTEX INDUSTRIES LIMITED
(b) NATIONALITY : An Indian Company
(c) ADDRESS : Survey No 91, Paikee Bhestan, Navasari-Surat Road, Sural - 395 023,
Gujarat (India)
3. PREAMBLE TO THE DESCRIPTION
The following specification particularly describes the invention and the manner in which it is to be performed:

Field of the Invention:
The present invention relates to the mixture of mono-substituted nitro dye to achieve deeper shade and a process for the colouration of synthetic textile materials. The disperse dyes are used for dyeing polyester and its blend with other fibers such as cellulose, polyurethane, nylon and wool by usual exhaust dyeing, continuous dyeing and direct printing.
Background of the invention and prior art:
Excellent fastness properties, particularly light fastness is required in the colouration of polyester fiber used in automotive industries. Based on currently available commercial automotive disperse dyes there is major limitation in the yellow range.
Traditionally Disperse Yellow 42 is widely used for the colouration of automotive textile polyester material because of better light fastness but this dyestuff has poor build up and sensitive to dye bath liquor ratio. Moreover, it also has poor exhaustion rate which causes the tarring problem after completion of dyeing cycle.
To overcome the problems of poor build up and dyeability of Disperse Yellow Dyes for the automotive application on polyesters, we have developed the mixtures of symmetrical and unsymmetrical nitro dyes which possess excellent dyeabilty and give very deep shade with excellent fastness properties particularly light fastness.

Objects of the Invention
It is an object of the present invention to provide novel Yellow disperse dyes having excellent dyeability for the coJoration of automotive textile polyester material.
It is another object of the present invention to provide novel Yellow disperse dyes having excellent dyeability such as good exhaustion rate and dye bath liquor ratio dependency while dyeing polyester material to be used in automotive textile.
It is yet another object of the present invention to provide a mixture of novel yellow disperse dyes with other dyes for colouration of polyester dyeing for automotive application.
It is another object of the present invention to provide a process for the colouration of automotive textile polyester material.
Summary of the invention
According to one aspect of the present invention, there is provided Novel Yellow nitro dyes of the formula (1)

Where, R1 is C1-C4Alkyl.
According to another aspect of the present invention, there is provided Disperse dye mixtures of the formula (1) with formula (2)

and formula (3)

wherein,
R3 is hydrogen, chloro, bromo, methoxy or C1-C4 Alkyl,
and
R4 is chloro, bromo, methoxy or C1-C4 Alkyl.
Description of present invention:
The present invention describes Novel Yellow nitro dyes of the formula (1)

Where, R1 is C1-C4 Alkyl.
The present invention further provides Disperse dye mixtures of the formula (1) with formula (2)


and formula (3)

wherein,
R3 is hydrogen, chloro, bromo, methoxy or C1-C4 Alkyl, and R4 is chloro, bromo, methoxy or C1-C4 Alkyl. This disperse dye mixtures are obtained by mixing
(a) 1 parts weight of formula (1) with
(b) 0.03-0.3 parts weight of formula (2) and
(c) 0.03-0.2 parts weight (preferably 0.05-0.15pts.wt) of formula (3). This disperse dye mixtures are preferably obtained by mixing

(a) 1 parts weight of formula (1) with
(b) 0.05-0.15 parts weight of formula (2) and
(c) 0.05-0.15 parts weight of formula (3).
The present invention further provides processes for syntheses of novel disperse nitro dyes and a process for the coloration of synthetic textile materials.

Novel disperse dyes claimed in the present invention have excellent light fastness on the polyester fiber and good dyeability, such as good exhaustion rate and dye bath liquor ratio dependency while dyeing.
Disperse dyes defined in the Formula (1) and the mixture dyes have excellent light fastness on the polyester fiber and the blend fiber with superior build up and better exhaustion rate. The present invention further provides excellent Yellow nitro dyes and the disperse dye mixtures which provide very good colour build up and light fastness properties on polyester and the blend fiber with good dyeability and high temperature dyeing stability.
Embodiment of the present invention will be described in more detail with reference to the following examples, in which parts are by weight unless otherwise stated.
The Present invention is concretely explained as follows, but the present invention is not limited to these examples.
Example
Example 1
The example 1 of structural formula (4) is synthesized as following method.
Structural formula (4)


3-nitro-4-chloro-sulfonyl chloride 138 g is added into the mixture of water 350 ml, sodium carbonate 62 g and aniline 51g at room temperature, and maintained for 3 hr at room temperature, and afterward p-toluidine 64 g is added into the reaction mass and heated up to 90~~95°C and maintained for 10 hr at same temperature. After reaction, the reaction mass is added into the mixture of 35% HC1 282 g and water 235 ml at 75oC and maintained for 1 hr. And then filter and wash with water to neutral PH. 220 g wet cake is obtained, and the solid content is 84.5%. The yield is 91%. The
λmax (in acetone) of example 1 dyestuff is 421 nm.
The wet cake is composed of formula (4) 91.0%, formula (2) (C.I.Disperse Yellow 42, abbreviated as Y-42) 3.2% and formula (5 Please confirm) 5.8%.

And then 2.0g of the obtained wet press cake is milled with 2.0g of naphthalenesulfonic acid-formaldehyde condensate and 50g of water and 500g 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 11.5g of the obtained finished liquid is added in the 100 ml of water and kept the PH 4.5 with acetic acid, and lOg piece of polyester is added into the dye bath for exhaust dyeing.
The dyeing bath is heated to 130°C and kept for 60min. After reduction cleaning
treatment, rinsing, washing and drying, the material is dyed a deep Yellow shade with the excellent washing fastness, light fastness and sublimation fastness. Moreover, the spend bath liquid (Dyeing liquid after exhaustion dyeing) is clean because of completely exhausting while dyeing.
Comparative example Comparative example 1:
The following dyes written as Dye 1-1 and Dye 1-2 each in the example 4 and example 8 of United State Patent No.4,851,575 are compared with dye written as Dye example 1 of this patent in exhaustion rate, build-up property and light fastness at same dyeing condition(l/lN depth) as example 1 as follows.
Dye example 1 of this patent surprisingly shows the excellent dyeability such as exhaustion rate and build-up property comparing to Comparative Dye 1-1 and Comparative Dye 1-2.


Dye
Exhaustion Dye bath liquor Build-up Light fastness
rate (%) .ratio dependency (%) property (1/1N) (LF) at 1/1 N
Example 1 of (his 95% 98% 100% 6 class
patent
Comparative Dye 70% 70% 75% 6 class
1-1 (Y-42) in
example 4 of
US4851575
Comparative Dye 85% 85% 88% 6 class
1 -2 in example 8
ofUS4851575
Light Fastness as per Test Method ISO 105 B02
Dyeing strength of 1/1N is dyed at 4.6%owf by using C.I disperse Yellow 42 as standard.
The exhaustion rate is measured by absorbance of dye liquor before (dye liquor) and after dyeing at same condition as example 1 (spent dye liquor) as the following formula.
Exhaustion Rate (%) = (Absorbance of dye liquor / Absorbance of spent dye liquor) x 100
Dye bath liquor ratio dependency (%) = (Dyeing strength(DS) at 10 of dye bath ratio/DS at 40 of dye bath ratio)xl00
The build-up property is measured by each dyeing strength (DS) between 4.6% owf. and 9.2% owf. as the following formula.
Build-up property (%) = {(Comparative dye DS at 9.2%/DS at 4,6%) / (Example! DS at 9.2%) / (Examplel DS at 4.6%)} x 100 .

Example 2
The dye stuffs synthesized by the similar method of example 1 are shown as follows:

Example R1 λmax (in acetone) (nm)
2-1 m-CH3 420
2-2 P-C2H5 422
2-3 P-C4H9 424

Dye Exhaustion Dye bath liquor Build-up Light
rate (%) ratio dependency
(%) property(l/lN) fastness (LF)
at
1/1 N
Example 95% 98% 100% 6 class
2-1
Example 97% 100% 100% 6 class
2-2
Example 96% 100% 100% 6 class
2-3
These dye stuffs also show the excellent exhaustion rate, build-up property and light fastness.

Example 3
The following mixture dyestuffs are synthesized by similar method of example 1 with alternatively switching the aniline and toluidine to each amine such as p-chloroaniline, p-anisidine and p-bromoaniline and so on. And also the each dyestuff may be produced by mixing each press cake before milling.

Dyestuff amount in % by weight based on the total weight of the mixture.

Example Formula
(1) Formula
(2) R3/R4 of Formula
(3) λmax(Acetone) nm
p-CH3/p-CH3
3-1 80 8 12 420
p-Cl /P-Cl
3-2 85 5 10 418
P-CH30/P-CH30
3-3 75 10 15 422
H/p-CH3
3-4 80 5 15 420
p-Cl/H
3-5 75 10 15 418
P-CH3O /H
3-6 80 5 15 421
p-C2H5/H
3-7 80 8 12 420
p-Br/H
3-8 80 5 15 418
These dye stuffs also show the excellent exhaustion rate, build-up property and light fastness.

We claim
1. Yellow nitro dyes of the formula (1)

Where, R1 is C1-C4 Alkyl. 2. Disperse dye mixtures of the formula (1) with formula (2)

and formula (3)
wherein,
R3 is hydrogen, chloro, bromo, methoxy or Cl-C4 Alkyl, and R4 is chloro, bromo, methoxy or C1-C4 Alkyl. 3. Disperse dye mixtures as claimed in claim 2 obtained by mixing
(a) 1 parts weight of formula (1) with
(b) 0.03-0.3 parts weight of formula (2) and
(c) 0.03-0.2 parts weight (preferably 0.05-0.15pts.wt.) of formula (3).

4. Disperse dye mixtures as claimed in claim 3 obtained by mixing:
(a) 1 parts weight of formula (1) with
(b) 0.05-0.15 parts weight of formula (2) and
(c) 0.05-0.15 parts weight of formula (3).

Wherein Rl is p-CH3; m-CH3; p-C2H5 and p-C4H9.
5. Yellow nitro dyes of the formula (1)