Abstract of
GB1406887
1406887 Dyestuff mixtures IMPERIAL CHEMICAL INDUSTRIES Ltd 22 May 1973 [29 June 1972] 30499/72 Addition to 1321902 Heading C4P [Also in Division D1] Dyestuff mixtures consist of (a) 10% to 60% by weight (based on the total weight of dyestuffs in the mixture) of a water insoluble dye free from sulphonic acid and carboxylic acid groups and of formula in which W<SP>1</SP> is H, Cl, Br, CN or acylamino group NHZ<SP>1</SP>, and W<SP>2</SP> is H, Cl, Br, CN, NO 2 provided that one of W<SP>1</SP> and W<SP>2</SP> is H; Z and Z<SP>1</SP> are each independently acyl groups of formula COV and SO 2 U, V is H or NH 2 or lower alkyl (C 1-4 ) lower alkoxy, phenyl or phenoxy radical optionally substituted, U is a lower alkyl or phenyl radical optionally substituted, Y is H, lower alkyl or lower alkoxy, R is lower alkyl or phenyl which may be substituted or a group of formula -A-COO-A<SP>1</SP>(X)m, A is an alkylene radical haying 1 to 6 carbon atoms, m is 1 or 2 and A<SP>1</SP> is a di- or tri-valent alkane radical depending upon the value of m containing up to 4 carbon atoms, X is CN, lower alkoxy, optionally substituted phenoxy, hydroxy, Cl, Br, lower alkoxycarbonyl, optionally substituted phenoxycarbonyl, carbonamido, carbonanilido, N-loweralkyl or N,N-di-lower alkyl carbonamido, NH 2 , anilino, N-lower alkylamino, N,N-di-lower alkylamino, lower alkylsulphonyl, phenyl sulphonyl or a radical UCO-or UCONH-, (b) from 30% to 90% by weight of (1) at least one disperse dye of formula which can contain up to 30% of its own weight of a disperse dye of formula in which L is a phenyl radical which may be substituted by one or more chlorine or bromine atoms or by hydroxy, NH 2 , lower alkyl, lower alkoxy, hydroxyloweralkoxy, N-lower alkylyamino, acylamino, N,N-di(lower alkyl)-amino, carbo lower alkoxy, lower alkoxycarbonyloxy or lower alkylcarbonyloxy groups, Q is a hydrogen atom or lower alkyl radical which may be substituted, and/or (ii) one or more disperse dyes of formula in which J and J<SP>2</SP> each independently represent a lower alkyl, amino lower alkyl, cyano lower alkyl, chloro lower alkyl, bromo lower alkyl, acylamino lower alkyl, hydroxy lower alkyl or lower alkoxy lower alkyl radicals or J<SP>1</SP> and J<SP>2</SP> are identical and each represent a substituted phenyl as defined for L provided that when dyes of Formula III and IV are both present the values of J<SP>1</SP>, J<SP>2</SP> and L are not identical and (c) 0% to 25% by weight (based on the total weight of the dyes present in the mixture) of at least one yellow to red disperse dystuff as defined. The dyestuff mixtures are obtained by mixing the dyestuffs in the required proportions.
NOTICE OF OPPOSITION GIVEN (SECT. 14/1949); CASE DECIDED BY THE COMPTROLLER ** SPECIFICATION AMENDED (SECT. 14/1949); + PATENT SEALED; AMENDMENT (SLIPS) PRINTED; - PATENT CEASED THROUGH NON-PAYMENT OF RENEWAL FEE
INPADOC patent family
1
DISPERSIONSFARBSTOFFGEMISCHE
Inventor: CHEETHAM IAN; DUNKERLEY KENNETH; (+3)
Applicant: ICI LTD
EC:C09B1/28; C09B1/32; (+2)
IPC: C09B1/28; C09B1/32; C09B1/514(+4)
Publication info: DE2333213 A1 - 1974-01-17
2
DISPERSE DYESTUFF MIXTURES
Inventor:
Applicant: ICI LTD
EC:C09B1/28; C09B1/32; (+2)
IPC: C09B1/28; C09B1/32; C09B1/514(+8)
Publication info: GB1406887 A - 1975-09-17
List of citing documents
Claims
WHAT WE CLAIM IS:
1. A process for the colouration of aromatic polyester textile materials which comprises applying to the said textile material by a dyeing, padding or printing process an aqueous dispersion of a dyestuff mixture consistingof: -
(a) from10% to60% by weight (based on the total weight of dyestuffs in the mixture) of a water insoluble monoazo dyestuff, free from sulphonic and carboxylic acid groups, which is of the formula:
EMI7.1
Formula I wherein
W1 is hydrogen, chlorine, bromine, cyano or an acylamino group of the
formulaNHZl, andW is hydrogen, chlorine, bromine, cyano or nitro,
provided that one of W1 and W2 is hydrogen;Z andZi each inde
pendently represent acyl groups of theformula -COV and SO2U; V is
a hydrogenatom or an amino group or a lower alkyl, lower alkoxy,
phenyl or phenoxy radical which can contain substituents; U is a lower
alkyl or phenyl radical which can contain substituents;Y is hydrogen,
lower alkyl or lower alkoxy;
R is a lower alkyl or phenyl radical which may contain substituents or a
group of the formula
EMI7.2
A is an alkylene radical containing from 1 to 6 carbon atoms;
n is 1 or 2, and A' represents a di- or tri-valent alkane radical, depending
on the value of n, containing up to 4 carbon atoms; and
X is cyano, lower alkoxy, optionally substituted phenoxy, hydroxy, chlorine,
optionally substituted phenylsulphonyl or a radical of the formula U .CO- or UCONH
(b) from 30% to <RTI 90 /O by weight (based on the total weight of dyestuffs in the mixture) of (i) at least one disperse anthraquinone dyestuff of the formula:-
EMI7.3
Formula II which can contain up to30 ,Ó of its own weight of a disperse anthraquinone dyestuff of theformula: -
EMI8.1
Formula III wherein L represents a phenyl radical which can be substituted by one or more chlorine or bromine atoms or by hydroxy, amino, lower alkyl, lower alkoxy, hydroxyloweralkoxy, N-lower alkylamino, acylamino, <RTI N:N-di(lower alkyl)amino, carbo lower alkoxy, lower alkoxycarbonyloxy or loweralkylcarbonyloxy groups; and Q is a hydrogen atom or a lower alkyl radical which may contain substituents, and/or(ii) one or more disperse anthroquinone dyestuffs of theformula:
EMI8.2
Formula IV wherein J1 andJ each independently represent a lower alkyl, amino lower alkyl, cyano lower alkyl, chloro lower alkyl,promo lower alkyl, acylamino lower alkyl, hydroxy lower alkyl or lower alkoxy lower alkyl radicals or J1 andj are identical and each represent a substituted phenyl radical as defined for L provided that when dyestuffs of
Formula III and Formula IV are both present the values of J1,J2 and L are not identical, and
(c) from 0 to25 ó by weight (based on the total weight of dyestuffs present in the mixture) of at least one yellow to red disperse dyestuff as hereinbefore defined.
2. A process as claimed in Claim 1 wherein J1 andJ each independently represent a lower alkyl, amino lower alkyl, cyano lower alkyl, chloro lower alkyl, bromo lower alkyl, acylamino lower alkyl, hydroxy lower alkyl or lower alkoxy lower alkyl radical.
3. A presence as claimed in Claim 1 or Claim 2 as hereinbefore particularly describedespecially with reference to any oneofthe Examples.
4. A dvestuff mixture comprising (a) from10?l- to60fxÓ by weight (based on the total weight of dyestuffs in the mixture) of a disperse azo dyestuff of Formula I.
(b)from 30% to9U ,Ó by weight (based on the total weight of dyestuffs in the mixture) of(i) a disperse anthraquinone dyestuff of FormulaII which can contain up to3OoÓ of its own weight of a disperse anthraquinone dyestuff of Formula III, and/or (ii) one or more disperse anthraquinone dyestuffs of Formula IV, and (c) from 0 to 25 ó by weight (based on the total weight of dyestuffs in the mixture) of at least one yellow to red disperse dyestuff as hereinbefore defined.
5. A dyestuff mixture as claimed in Claim 4 which additionally contains one or more dispersing agents.
6. A dyestuff mixture as claimed in Claim 4 or Claim 5 wherein J1 and J have the meanings specified in Claim 2.
7. A dyestuff mixture as claimed in any one of Claims 4 to 6 as hereinbefore particularly described especially with reference to any one of the Examples.
Description
(54) DISPERSE DYESTUFF MIXTURES
(71) We, IMPERIAL CHEMICAL INDUSTRIES LIMITED, of Imperial
Chemical House, Millbank, London, S.W.1, a British Company, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to beperformed, to be particularly described in and by the following statement:
This invention relates to mixtures of disperse dyestuffs and their use for colouring aromatic polyester textilematerial.
In British Application No.3O181//01 and 6671/71 (Serial No. 1321902) there is described and claimed the water-insoluble monoazo dyestuffs, free from sulphonic and carboxylic acid groups, which are of theformula: -
EMI1.1
wherein
W1 is hydrogen, chlorine, bromine, cyano or an acylamino group of the formula
No7,: and W2 is hydrogen, chlorine, bromine, cyano or nitro, provided that
one of W' and W2 is hydrogen; Z andZt each independently represent acyl
groups of theformulaCOV andSO.2U; V is a hydrogen atom or an amino
group or a lower alkyl, lower alkoxy, phenyl or phenoxy radical which can
contain substituents; U is a lower alkyl or phenyl radical which can contain
substituents;Y is hydrogen, lower alkyl or lower alkoxy;
R is a lower alkyl or phenyl radical which may contain substituents or a group of
the formula
EMI1.2
A is an alkylene radical containing from 1 to 6 carbon atoms; n is 1 or 2, and A' represents a di- or tri-valent alkane radical, depending on the
value ofn, containing up to 4 carbon atoms and
X is cyano, lower alkoxy, optionally substituted phenoxy, hydroxy, chlorine,
phenylsulphonyl or a radical of the formulaU. CO-, U.COO- or <RTI U.CONH-.
The said Application also describes and claims a process for colouring aromatic polyester textile materials which comprises applying to the textile material by a dyeing, padding or printing process an aqueous dispersion of one of the said dyestuffs. The
Application also discloses that the said dyestuffs can be applied in conjunction with other disperse dyestuffs.
It has now been found that particularly valuable classes of disperse dyestuffs which can be used in conjunction with the above azo dyestuffs arel-hydroxy-4-arylamino- anthraquinones and/or1: 4-di(aikylamino) anthraquinones.
According tc the present invention, which is an improvement in or modification of the invention which is described and claimed in British Application No. 30181/70 and 6671/71 (Serial No. 1321902), there is provided a process for the colouration of aromatic polyester textile materials which comprises applying to the said textile material by a dyeing, padding or printing process an aqueous dispersion of a dyestuff mixture consistingof: -
(a) from10 to60 S, by weight (based on the total weight of dyestuffs in the mixture) of a water insoluble monoazo dyestuff, free from sulphonic and carboxylic acid groups, which is of theformula : -
EMI2.1
<RTI Formula I wherein
W1 is hydrogen, chlorine, bromine, cyano or an acylamino group of the
formulaNHZ1, andW is hydrogen, chlorine, bromine, cyano or nitro,
provided that one ofW1 and W2 is hydrogen; Z and Z1 each inde
pendently represent acyl groups of theformulaCOV andSO,U; V
is a hydrogen atom or an amino group cr a lower alkyl, lower alkoxy,
phenyl or phenoxy radical which can contain substituents; U is a lower
alkyl or phenyl radical which can contain substituents;Y is hydrogen,
lower alkyl or lower alkoxy;
R is a lower alkyl or phenyl radical which may contain substituents or a
group of the formula
EMI2.2
A is analkylene radical containing from 1 to 6 carbon atoms;
n is 1 or 2, and A' represents a di- or tri-valent alkane radical, depending
on the value of n, containing up to 4 carbon atoms; and
X is cyano, lower alkoxy, optionally substituted phenoxy, hydroxy, chlorine,
optionally substituted phenylsulphonyl or a radical of the formula U.CO- or UCONH--,
(b) from 30n/, to 90% by weight (based on the total weight of dyestuffs in the mixture) of (i) at least one disperse anthraquinone dyestuff of the formula: -
EMI2.3
Formula II which can contain up to <RTI 30 Ó of its own weight of a disperse anthraquinone dyestuff of theformula:
EMI3.1
Formula111 wherein L represents a phenyl radical which can be substituted by one or more chlorine or bromine atoms or by hydroxy, amino, lower alkyl, lower alkoxy, hydroxyloweralkoxy, N-lower alkylamino, acylamino, N:N-di (loweralkyl)amino, carbo lower alkoxy, loweralkoxycarbonyloxy or loweralkylcarbonyloxy groups; and Q is a hydrogen atom or a lower alkyl radicalwhich may contain substituents, and/or(il) one or more disperse anthraquinone dyestuffs of theformula: -
EMI3.2
Formula IV wherein <RTI J' and2 each independently represent a lower alkyl, amino lower alkyl, cyano lower alkyl, chloro lower alkyl, bromo lower alkyl, acylamino lower alkyl, hydroxy lower alkyl or lower alkoxy lower alkyl radicals or J1 and J2 are identical and each represent a substituted phenyl radical as defined for L provided that when dyestuffs of Formula III and Formula IV ere both present the values ofJ1, J2 and L are not identical, and c) from 0 to 25% by weight (based on the total weight of dyestuffs present in the mixture) of at least one yellow to red disperse dyestuff as hereinafter defined.
Throughout this specification the terms "lower alkyl" andlower alkoxy" are used to denote alkyl and alkoxy radicals respectively containing from 1 to 4 carbon atoms. Examples of the symbolsWt, W2, Y, Z, R, A,A1, X, V, U and n are given in
British Application No. 30181/70 and 6671/71 (Serial No.1321902).
As examples ofthe groups which may be present as substituents on the phenyl radical represented by J1,I and L there may be mentioned methyl, ethyl, methoxy,ethoxy, -hydroxyethoxy, propoxy, butoxy, methyl amino, dimethylamino,diethylammo, carbomethoxy, carboethoxy,methoxycarbonyloxy, acetyloxy, formylamino, acetylamino, propionylamino and benzovlamino.
As examples of the radicals represented by Jt and J2 there may be mentioned methyl, ethyl,n-propyl, n-butyl, isopropyl,-hydroxyethyl, ss- or y-hydroxypropyl,8-(methoxy ormethoxy) ethyl,ce-(chloro- orbromo-)ethyl"e-(acetylamino), ethyl,v- methoxypropyl, dihydroxypropyl,sec-butyl, -amino ethyl andP-cyanoethyl.
As examples of the lower alkyl radicals which may contain substituents represented by Q there may be mentioned methyl, ethyl, propyl, butyl, benzyl,p-phenylethyl, chlorobenzyl, methoxybenzyl,alninobenzyl, hydroxybenzyl, acetylaminobenzyl and 2furfurylmethyl.
The colouring process of the present invention can be carried out by the methods which are described and claimed in British Application No.30181/70 and 6671/71 (Serial No. 132190) using the said mixtures of azo and anthraquinone dyestuffs as hereinbefore defined.
The azo dyestuffs of Formula I can be obtained by the method which is described and claimed in British Application No. 30181/70 and 6671/71 (Serial No. 1321902).
The dyestuffs of Formula II can themselves be obtained, for example, by the condensation of a mixture of quinizarin and leucoquinizarin optionally containing in the 2-position a lower alkyl radical which may be substituted with an arylamine of the formulaL-NH,, wherein L has the meaning stated above, in the presence of boric acid and a liquid such as water and/or water-miscible organic liquid. Whilst the initial condensation product (i.e. Formula II) is obtained, some bis-condensation usually occurs so that the product comprises a mixture of the dyestuffs of Formulae II and III. However, the reaction is carried out under such conditions that the formation of the dyestuff of Formula III is kept to a minimum and in no event exceeds 30%, and in fact is preferably less than20%, by weight of the dyestuff of Formula II.
The dyestuffs of Formula IV can be obtained by condensing a mixture of quinizarin and leucoquinizarin with one or two different aliphatic amines of the formulaJ'NH2, wherein J1 has the meaning stated above, the reaction being carried out in water and/or a water soluble organic liquid, and optionally in the presence of boric acid. When a mixture of two such amines is used then the resulting product is a mixture of the two symmetrical dyestuffs and theursymmetrical dyestuff.
The yellow to red disperse dyestuffs which can be present in the dyestuff mixtures of the invention can be any of the yellow to red disperse dyestuffs which are conventionally employed in dyeing aromatic polyester textile materials, and the shades of which fall within the areas 1 to 9 inclusive of the Hue Indication Chart in the third edition of the Colour Index whichwas published by The Society of Dyes and Colourists in 1971. Such dyestuffs are described in, for example, the third edition of the Colour
Index or in British Specifications Nos. 1256093, 1256355 and 1256714.
Accordingte a further feature of the invention there is provided a dyestuff mixture comprising a) from 10% to 60% by weight (based on the total weight of dyestuffs in the mixture) of a disperse azo dyestuff of Formula I.
b) from 30% to90 Ó by weight (based on the total weight of dyestuffs in the mixture) of i) a disperse anthraquinone dyestuff of Formula II which can contain up to 30% of its own weight of a disperse anthroquinone dyestuff of Formula III, and/or ii) one or more disperse anthraquinone dyestuffs of Formula IV, and c) from 0 to250;, by weight (based on the total weight of dyestuffs in the mixture) of at least one yellow to red disperse dyestuff as hereinbefore defined.
The dyestuff mixtures of the invention can be obtained by simply mixing the various componentstogether in the required proportions. Since, however, the said mixtures are to be used for dyeing aromatic polyester textile materials from aqueous dyebaths the mixtures generally contain in addition one or more of the dispersing agents which are conventionally employed in preparing commercially available forms of disperse dyestuffs, and such mixtures form a further feature of the present invention.
Such mixtures can be obtained by milling or grinding together the various dyestuff components in the stated proportions in the presence of one or more dispersing agents and, if desired,ir. the presence of water and subsequently removing the water from the resulting dispersion and/or standardising the mixture by the addition of conventional diluents such as dispersing agents,de-dusting agents and/or water-soluble organic liquids.
By the process of the invention aromatic polyester textile materials are coloured in blue to black shades possessing excellent fastness to light, tol wet treatment and to dry heat treatments.
The invention is illustrated by the following Examples in which the parts and percentages are by weight.
Example 1
100 Parts of a woven polyethylene terephthalate textile material are immersed in adyebatl comprising a dispersion of 2 parts of the dyestuff mixture, obtained as described below, in 3,000 parts of water containing 1 part of the disodium salt of bis (2-sulphonaphth-1-yl) methane and 1 part of the sodium salt of a sulphated cetyl/ oleyl alcohol mixture, and dyeing is then carried out for 1 hour at13(40C. under superatmospheric pressure.The dyed textile material is then removed from the dyebath, rinsed in water, treated for 15 minutes at 500C. in an aqueous solution containing0.20,0, of sodium hydroxide and0.2 of sodium hydrosulphite, rinsed in water, "soaped" for10 minutes in a0.2% aqueous solution of a synthetic detergent at 1000C., rinsed again in water and is finally dried.
The textile material is thereby dyed a navy blue shade having excellent fastness to light and to dry heat treatments.
The dyestuff mixture used in the above Example was obtained by intimately mixing together 0.6 part of the second dyestuff of Example 2 of British Application No.
30181/70 and6671/71 (Serial No. 1321902) and 1.4 parts of a85:15 mixture of1-hydroxy-4- ss-hydroxyethoxv' anilino] anthraquinone and 1:4-di[p-tss-hydroxy- ethoxy) anilino] anthraquinone. This mixture of anthraquinone compounds was itself obtained by heating a mixture of 7.68 parts of quinizarin, 1.94 parts of leucoquinizarin, 7.35 parts of8-(p-anrinop & oxy) ethanol, 5.4 parts of boric acid, 24 parts of ethanol and 15 parts of water for 11 hours at85 C, cooling to 150C, and filtering off the precipitated solid which was washed with aqueous alcohol, then with a1 % aqueous solution of sodium hydroxide, and finally water, and dried.
Example 2
In place of the 2 parts of the dyestuff mixture used in Example 1 there are used 2 parts of the dyestuff mixture obtained by mixing together 1.4 parts of a 85:15 mixture ofl-hydroxy-4-anilinoanthraquinone and 1:4di(anilino)anthraquinone and 0.6 part of the second dyestuff of Example 2 of British Application No. 30181/70 and 6671/71 (Serial No. 1321902). A navy blue dyeing of good light fastness is obtained.
Example 3
In place of the 2 parts of the dyestuff mixture used in Example 1 there are used 2 parts of the dyestuff mixture obtained by intimately mixing together 1.4 parts of the anthraquinone dyestuff mixture obtained by condensing a mixture of quinizarin and leucoquinizarin with a mixture of p-phenylenediamine and p-aminoacetanilide and 0.6 part of the second dyestuff of Example 2 of British Application No. 30181/70 and 6671/71 (Serial No.1321902,). A navy blue dyeing of excellent fastness to light and to dry heat tleatments is obtained.
Example 4
In place of the 2 parts of the dyestuff mixture used in Example 1 there are used 2 parts of the dyestuff mixture obtained by intimately mixing together 1.2 parts of the anthraquinone dyestuff mixture obtained by condensing a mixture of quinizarin and leucoquinizarin with a mixture of p-aminoacetanilide and p-aminopropionanilide and 0.8 part of the second dyestuff of Example 2 of British Application No.
30181/70 and 6671/71 (Serial No. 1321902). A navy blue dyeing of excellent fastness to light and to dry heat treatments is obtained.
Example 6
In place of the 1.4 parts of the mixed anthraquinone dyestuff present in the dyestuff mixture used in Example 1 there are used 1.4 parts of each of the mixed anthraquinone dyestuffs which are similarly obtained by replacing the 7.35 parts of,8(p-aminophenoxy) ethanol by (a) 5.9 parts of p-anisidine (b) 5.15 parts of m-toluidine (c) 6.6 parts of4-(p-hydroxyethyl)aniline (d) 6.55 parts ofp-atninoacetanilide (e) 5.85 parts of p-aminoformanilideQ 5.25 parts ofm-hydroxyaniiine, and (g) 6.15 parts ofp-chloroaniline.
In each case deep navy dyeings of excellent light fastness are obtained.
Example 7
In place of the 2 parts of the dyestuff used in Example 1 there are used 2 parts of the dyestuff mixture obtained by intimately mixing together 1.0 parts of a85:15 mixture ofl-hydroxy-Ganilinoanthraquinone and1: 4-di(anilino)anthraquinone (Component A), 0.6 part of1-hydroxy-2-furfurylmethyl-4-anilinoanthraquinone (Component B) and 0.4 part of the second dyestuff (Component C) of Example 2 of British
Application No. 30181/70 and 6671/71 (Serial No. 1321902). A navy blue dyeing of excellent light fastness is obtained.
In place of the 2 parts of the mixture used in this Example there is used a mixture of 1.0 part of Component A, 0.8 part of Component B and 0.2 part of Component C or a mixture of 0.8 part of Component A, 0.8 part of Component B and 0.4 part of
Component C when similar dyeing are obtained.
The mixture of l-hydroxy-4-anilinoanthraquinone and 1: 4-dianilinoanthraquinone (ComponentA) used in the above Example was itself obtained by heating a mixture of 81 parts of quinizarin, 27 parts of leucoquinizarin, 378 parts of ethanol, 126 parts of water, 54 parts of boric acid and 63 parts of aniline for 12 hours at the boil. 36
Parts of sodium hydroxide and 18 parts of sodiumrn-nitrobenzenesulphonate are added and heated at the boil for a further hour. The mixture is cooled and the solid is filtered off, washed with water and dried.
The 1-hydroxy-2-furfurylmethyl-4-anilinoanthraquinone(Component-B3, was itself obtained by heating a mixture of 4 parts of2-furfurylmethylquinizarin, 30 parts of aniline, 1.25 parts of zinc dust, 2 parts of water, 24 parts of ethanol, 1.25 parts of boric acid and101 parts of concentrated hydrochloric acid for 11 hours at the boil. The mixture was then cooled and the precipitated solid filtered off, washed with water, then with methanol and dried.
Example 8
In place of the 2 parts of the dyestuff mixture used in Example 1 there are used 2 parts of the dyestuff mixture which was obtained by intimately mixing together 30 parts of the second dyestuff of Example 2 of British Application No. 30181/70 and 6671/71 (Serial No. 1321902), 30 parts of 1-methylamino-4-ss-hydroxyethylamino- anthraquinone and 140 parts of an 85:15 mixture of1-hydroxy-4-[p-(ss-hydroxy- ethoxy)anilino] anthraquinone and 1: 4-di[p-(/-hydroxyethoxy)anilino] anthraquinone. A navy blue dyeing of excellent fastness properties is obtained.
In place of the 30 parts of 1-methylamino-4-ss-hydroxyethylamino used in the above mixture there are used 30 parts of1: 4-di(isopropylamino)anthraquinone. The resulting mixture gives a navy blue dyeing of excellent fastness properties when applied as described in Example 1.
Example 9
A dyestuff mixture is prepared by intimately mixing together 50 parts of the second dyestuff of Example 2 of British Application No. 30181/70 and 6671/71 (Serial
No.1321902), 10 parts of 1:4-di(p-toluidino)anthraquinone and 140 parts of an 85: 15 mixture of 1 - hydroxy - 4 - [p(ss - hydroxyethoxy)anilino]anthraquinone and 1:4di [p-(phydroxyetl'oxy)anilino] anthraquinone.
When the mixture is applied to an aromatic polyester textile material by the method described in Example 1 a navy blue dyeing of excellent fastness properties is obtained.
Example 10
A dyestuff mixture is prepared by intimately mixing together 50 parts of the dyestuff of Example 1 of British Application No. 30181/70 and 6671/71 (Serial No.
1321902), 30 parts of an 85:15 mixture ofl-hydroxy-4- rp-(P-hydroxyethoxy)anilino ] anthraquinone and 1:4 -di[o - (ss-hydroxyethoxy)anilino]anthraquinone, 10 parts of
1 - methyl - 3 - cyano - 4 - methyl - 5 - (o - nitrphenylazoss - 6 - hydroxypyrid - 2 one and 10 parts of 1-phenylazo-4-(p-hydroxyphenylazo)naphthalene.
When the mixture is applied to an aromatic polyester textile material by the method described in Example 1 a black dyeing of excellent fastness properties is obtained.
Example 11
In place of the 0.6 parts of the second dyestuff of Example 2 of British Application
No.30181/70 and 6671/71 (Serial No. 1321902) used to prepare the dyestuff mixturecf Example 1 above there are used01.6 parts of the dyestuff of Examples 1, 9 or 11 of the same Application when mixtures are obtained which give similar navy blue shadeswhen applied to an aromatic polyester textile material.
Example 12
A dyestuff mixture is prepared by intimately mixing together 20 parts of the dyestuff of Example 1 of British Application No.30181/70 and 6671/71 (Serial No.
1321902) and180 parts of1-hydroxy-2-ethyl-4-(p-hydroxvanilino)anthraquinone. When applied to an aromatic polyester textile material by the method described in Example 1 a navy blue dyeing of excellent fastness properties is obtained.
Example 13
In place of the 0.6 part of the1-hydroxy-2-furfurylmethyl-4-anilinoanthraquinone used to obtain the dyestuff mixture described in Example 7 above there is used 0.6 part of any of the followingdye stuffs whereby mixtures are obtained which give navy blue dyeings of excellent fastness properties when applied to an aromatic polyester textilematerial: : (a) <RTI 1 hydroxy-2-ethyl-4-anilinoanthraquinone, (b) 1-hydroxy-2-n-butyl-4-anilinoanthraquinone, (c)1-hydroxy-2-ethyl-4-(n'-hydroxyanilino) anthraquinone, (d)1-hydroxy-2-furfurylmethvl-4-(o-anisidino)anthraquinone, (e)1-hydroxy-2-ethyl-4-(p-hydroxyanilino3anthraquinone, (f) 1-hydroxy-2-ethyl-4-(p-anisidino)anthraquinone, (g)1-hydroxy-2-benzyl-4-p-anisidino)anthraquinone, (h) 1-hydroxy-2-sec-butyl-4-(p-anisidino)anthraquinone, and(i) 1 -hydroxy-2-furfurylmethyl-4-(p-toluidino)anthraquinone.
