Note: Descriptions are shown in the official language in which they were submitted.
3~
-- 1 --
Case 1-1499~
Reactive dyes, process for their preparation and use thereof
The present invention relates to reactive dyes and to the use thereof
for dyeing or printing textile fibre materials.
Specifically, the present invention relates to reactive dyes of the
formula
~ ~ 2
~ N = N -o~;f ~1 - N = N ~ o ~ \~ z
3H~o32 ~`so ~1 (s~3xH)o-2
Cl 3 Cl
wherein each of Zl and Z2 independently of the other is a radical
of the formula
1 (2),
Rl is alkyl which may be substituted by hydroxy, alkoxy, hydroxyalkoxy,
alkylcarbonyl, alkoxycarbonylz alkylcarbonyloxy, carboxy, cyano,
chlorine, sulfo or sulfato, and R2 is hydrogen, alkyl which may be
substituted by hydroxy, alkoxy, hydroxyalkoxy, alkylcarbonyl, alkoxy-
carbonyl, alkylcarbonyloxy, carboxy, cyano, chlorine, sulfo or sulfato,
or is phenyl, benzyl or phenethyl, the benzene ring of which may be
substituted by methyl, methoxy, acetylamino, chlorine, bromine,
carboxy or sulfo, and the benzene rings ~ and B may be further
substituted.
The substituent Rl is straight chain or branched and preferably
contains 1 to 6 carbon atoms. Examples of Rl are the Eollowing
, '`~1,;, 1 ` ~
3~
substituents: carboxymethyl, ~-carboxyethyl, ~-carboxypropyl, methoxy-
carbonylmethyl, ethoxycarbonylmethyl, ~-methoxyethyl, ~-ethoxyethyl,
~-methoxypropyl, ~-chloroethyl, y-chloropropyl, y-bromopropyl,
j~-hydroxyethyl, y-hydroxypropyl, ~-hydroxybutyl, ~-cyanoethyl~ sulfo-
methyl, ~-sulfoethyl and j~-sulfatoethyl. If the substituent R2 is an
alkyl radical, it is straight chain or branched and likewise preferably
contains 1 to 6 carbon atoms; R2 may be further substituted, as
indicated above for formula (2). Examples of R2 are: methyl, ethyl,
propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl
and n-hexyl, as well as the substituents cited above as examples of Rl.
As a non-aliphatic substituent, R2 is preferably the phenyl radical.
Examples of further substituents at the benzene rings A and B are~
alkyl groups containing 1 to 4 carbon atoms such as methyl, ethyll
propyl, isopropyl or butyl, alkoxy groups containing 1 to 4 carbon
atoms such as methoxy, ethoxy, propoxy, isopropoxy or butoxy, acyl-
amino groups containing 2 to 4 carbon atoms such as acetylamino,
propionylamino or butyrylamino, amino, alkylamino containing 1 to 4
carbon atoms such as methylamino, ethylamino, propylamino~ isopropyl-
amino or butylamino, alkoxycarbonyl containing 1 to 4 carbon atoms
in the alkoxy moiety such as methoxycarbonyl or ethoxycarbonyl, alkyl-
sulfonyl containing 1 to 4 carbon atoms such as methylsulfonyl or
ethylsulfonyl, trifluoromethyl, nitro, cyano, halogen such as
fluorine, chlorine or bromine, carbamoyl, N-alkylcarbamoyl containing
1 to ~i carbon atoms in the alkyl moiety such as N-methylcarbamoyl or
N-ethylcarbamoyl, sulfamoyl, N-alkylsulfamoyl containing 1 to 4 carbon
atoms such as N-methylsulfamoyl, N-ethylsul~amoyl, N-propylsulfamoyl~
N-isopropylsulfamoyl or n butylsulfamoyl, ureido, hydroxy, carboxy or
sulfomethyl. A and B preEerably contain as further substituents
methyl, ethyl, methoxy, ethoxy, acetylamino, chlorine, bromine, ureido,
hydroxy, carboxy or sulfomethyl.
The reactive dyes of formula (1) contain two removable chlorine atoms
which can react in the manner of a nucleophilic substitution and are
therefore fibre-reactive~
By fibre-reactive compounds are meant those compounds which are able
to react with the hydroxyl groups oE cellulose, with the amino, carbo-
xyl, hydroxyl and thio groups of wool and silk, or with the amino
groups and, if present, carboxyl groups of synthetic polyamides to
form covalent chemical bonds.
Preferred embodiments of the reactive dyes of formula (1) are:
a) Reactive dyes of formula (1), wherein the coupling component is
l-amino-8-hydroxynaphthalene-3,6-disulfonic acid, and Zl' Z2' A and
B are as defined for formula (1).
b) Reactive dyes of formula (1), wherein Zl has the same meaning as
Z2' and the benzene rings A and B contain no further substituents
apart from O to 2 sulfo groups.
c) Reactive dyes of formula (1), wherein each of the benzene rings A
and B contains a sulfo group.
d) Reactive dyes of the formula
Z -~ ~ -NH ~ N = N ~ N ~ N
~ ~ S03H 3 3 ~03S
wherein Zl and Z2 are as defined for formula (2).
e) Reactive dyes of formula (3), wherein Zl and Z2 are hydroxy-Cl-C4-
alkylamino, N-Cl-C~alkyl-N-hydroxy-Cl-C4alkylamino, N,N-dihydroxy-
Cl-C4alkylamino or N-phenyl-N-ilydroxy-Cl-C~alkylamino.
~33~3~
f) Reactive dyes of the formula
~ ~ 2
Z~ -NH~ N = N ~ N = N - It ~-NH~ -Z2
~1 \o~ \SO H HO 5/ ~o/ \o~ \SO H HO S/ \
(4) ,
wherein Zl and Z2 are as defined in e).
g) Reactive dyes of formula (4), wherein Zl and Z2 are ~-hydroxyethyl-
amino, N,N-di-~-hydroxyethylamino9 N-methyl-N-~-hydroxyethylamino,
N-ethyl-N-~-hydroxyethylamino, tri(hydroxymethyl)methylamino or
N-phenyl-N-~-hydroxyethylamino.
Particularly prefered is:
h) The reactive dye of the formula
. H~ ~H2
HOCH2C~2h~- ~ ~-NH~ t - N = N - ~ N = N ~ I-NH- ~ ~ -NHCH2C~20H
\S~H HO S/ ~4/ \~ \SO ~ ~10 S/ \
(S)
The process for the preparation of reactive dyes of formula ~1)
comprises coupling and condensing, in suitable sequence, l-amino-8-
hydroxynaphthalene-3,6-disulfonic acid or 1-amino-8-hydroxynaphthalene-
~,6-disulfonic acid, benzenediazo components (A) and (B), 2,~,6-tri-
chloro-s-triazine and amino compounds (Zl) and/or (Z2)
As the individual process steps referred to above can be carried out
in varying sequence and, if desired, in some cases can be cflrried
out simultaneously, different variants of the process are possible. In
general, the reaction is carried out stepwise in succession, with the
~2~33~3~
-- 5 --
sequence of the simple reactions between the individual reactants
conveniently being chosen in accordance with the special conditions.
It is known to carry out coupling first in acidic medium in the
o-amino position and then in alkaline medium in the o-hydroxy position
since l-amino-8-naphtholSulfonic acids which are first coupled in
alkaline medium (o-hydroxyazo dyes) can not be further coupled to
give disazo dyes.
Important process variants comprise:
1) condensing 2 mol of 2~4,6-trichloro-s-triazine with 1 mol of a
disazo compound of the formula
H2N\ ~ I ~ 2 ~ 2
~ N = ~ - a~ N = N ~ o
\SO H HO S/ ~ \SO H HO S/
and condensing the resultant diprimary condensation product in the
molar ratio of 1:2 with an equimolar mixture of amines (Zl) and (Z2)
to give a reactive dye of formula (4);
2) condensing 2 mol of 2,4,6-trichloro-s-triazine with 2 mol of an
amine (Zl) or (Z2) and condensing the resultant primary condensation
product with 1 mol of a disazo compound of formula (6) to give a
reactive dye of formula (4)~ (Zl = Z2);
3) condensing 2 mol of 2,4,6-trichloro-s-triazine with 1 mol of a
disazo compound oE formula (6) and condensing the resultant diprimary
condensation procluct with 2 mol of an amine (Zl) or (Z2) to give a
reactive dye of formula (4)~ (Zl a Z2);
4) condensing 2 mol of 2,4,6-trichloro-s-triazine with 2 mol of
1,3-phenylenediamine-4-sulfonic acid, condensing the primary conden-
sation product with 2 mol of an amine (Zl) or (Z2)' diazotising the
3~3
resultant secondary condensation product and then effecting coupling,
first in strongly acidic solution and then in neutral solution~ with
l-amino-8-hydroxynaphthalene-3,6-disulfonic acid to give a reactive
dye of formula (4) 9 (Zl = Z2);
S) condensing 2 mol of 2,4,6-trichloro-s-triazine with 2 mol of
1,3-phenylenediamine-4-sulfonic acid, diazotising the primary conden-
sation product and then effecting coupling, first in strongly acidic
solution and then in neutral solution, with l-amino-8-hydroxynaphtha-
lene-3,6-disulfonic acid, and condensing the resultant disazo dye with
2 mol of an amine (Zl) or (Z2) to give a reactive dye of formula (4),
(Zl Z2)
The procedure is the same when using l-amino-8-hydroxynaphthalene-
4,6-disulfonic acid as coupling component or where using other diazo
components, e.g. 1,4-phenylenediamine-2-sulfonic acid.
The disazo compounds of formula (6) are prepared by coupling 1,8-amino-naphthol-3,6-disulfonic acid with 2 equivalents of diazotised
5-nitraniline-2-sulfonic acid (acidic and alkaline coupling) and sub
sequently reducing the nitro groups or by coupling 1,8-amino-
naphthol-3,6-disulfonic acid with 2 equivalents of diazotised S-acetyl-
aminoaniline-2-sulfonic acid and subsequently sapOnifying the acetyl-
amino groups. In practice,the acid coupling is carried out by adding
a solution of l-amino-8-hydroxynaphthalene-3,6-disulfonic acid to
the strongly acidic diazo suspension. The subsequent alkaline COUp-
ling is effected in known manner in weakly alkaline medium. It is
preferred to carry out the coupling of the monoazo compound with a
further equivalent of the diazo components in alkaline bicarbonate
solution. The saponification of the two acetylamino groups a~ter
completion of the alkaline coupling is carried out in known manner
with alkaline compositions. It is preferred to carry out the
saponification with sodium ilydroxide.
3~
It is preferred to carry out the condensation of the 2,4,6-trichloro-
s-triazine with the amines (Z]) and/or (Z2) and the disazo compound of
formula (6) or the diazo components (A) and (B) in aqueous solution
or suspension, at low temperature and at a weakly acidic, neutral to
weakly alkaline pH value. It is advantageous to neutralise the hydrogen
halide set free during the condensation by the continuous addition of
aqueous alkali metal hydroxide, carbonate or bicarbonate.
Possible starting materials which can be used for the preparation of
reactive dyes of form~lla (1) are listed individually below:
Coupling components:
. . _ . , _
l-amino-8-hydroxynaphthalene-376-disulfonic acid (H acid),
l-amino-8-hydroxynaphthalene-4,6-disulfonic acid (K acid).
Diazo components
_ _
1,3-diaminobenzene 9 1,4-diaminobenzene, 1,3-diamino-4-chlorobenzene,
1,3-diamino-4-methylbenzene, 1,3-diamino-4-ethylbenzene9 1,3-diamino-
4-methoxybenzene, 1,3-diamino-4-ethoxybenzene, 1,4-diamino-2-methyl-
benzene, 1,4-diamino-2-methoxybenzene, 1,4-diamino-2-ethoxybenzene,
1,4-diarnino-2-chlorobenzene, 1,4-diamino-2,5-dimethylbenzene,
1,4-diamino-2,5-diethylbenzene, 1,4-diamino-2-methyl-5-methoxybenzene,
1,4-diamino-2,5-dimethoxybenzene, 1,4-diamino-2,5-diethoxybenzene~
1,3-diamino-2,4,6-trimethylbenzene, 1,4-diamino-2,3,5,6-tetramethyl-
benzene, 1,3-diamino-4-nitrobenzene, 1,4-diaminobenzene-2-sulfon;c acid,
1,4-diaminobenzene-2,5-disulfonic acid, 1,4-diaminobenzene-2,6-di-
sulfonic acid, 1,3-diaminobenzene-4-sulfonic acid, 1,3-diaminobenzene-
4,6-disulfonic acid, 1,4-diamino-2-chlorobenzene-S-sulfonic acid,
1,4-diamino-2-methylbenzene-5-sulfon;c acid, 1,5-diamino-6-methyl-
benzene-3-sulfonic acid, 1,3-diamino-6-methylbenzene-4-sulfonic acid,
1,4-diaminobenzene-2-carboxylic acid, 1,3-diaminobenzene-4-carboxylic
acid, 1,2-diaminobenzene-4-carboxylic acid, 1,3-diaminobenzene-5-
~33~3
carboxylic acid, l-amino-4-methoxy-5-aminomethylbenzene-6-sulfonic
acid, l-amino-3-nitrobenzene-6-sulfonic acid or 1-amino-4-nitrobenzene-
6-sulfonic acid.
If an aminoacetylamino compound is to be used as diazo component
instead of a diamine, from which compound the acetyl group is subse-
quently removed by saponification as explained above in the
description of the process variants, it may be a monoacetyl compound
of one of the diazo components listed above, e.g. l-amino-4-acetyl~
aminobenzene-2-sulfonic acid or 1-amino-4-acetylaminobenzene-3-
sulfonic acid, l-amino-3-acetylaminobenzene-4-sulfonic acid or
l-amino-3-acetylaminobenzene-6-sulfonic acid, 1-amino-3-acetylamino-
benzene-4,6-disulfonic acid, 1-amino-4-acetylaminobenzene-2,5-
disulfonic acid or l-amino-4-acetylaminobenzene-2,6-disulfonic acid,
l-amino-3-acetylamino-4-methylbenzene-6-sulfonic acid.
Reactive component:
2,4,6-trichloro-s-triazine (cyanuric chloride)~
Amines (Zl) and (~2)
methoxyethylamine, ethoxyethylamine, methoxypropylamine, chloroethyl-
amine, hydroxyethylamine, dihydroxyethylamine, hydroxypropylamine,
aminoethanesulfonic acid, ~-sulfatoethylamine, N-phenyl-N-~-hydroxy-
ethylamine, N-methyl-N-~-hydroxyethylamine, N-ethyl-N-~-hydroxyethyl-
amine, tri(hydroxymethyl)methylamine.
The reactive dyes of formula (1) are suitable Eor dyeing and printing
a very wide range oE materials such as silk, leather, wool, polyamide
Eibres and polyurethanes, and especially cellulosic Eibre materials
of all kinds. ~xamples oE such fibre materials are natural cellulose
fibres such as cotton, linen and hemp, as well as cellulose and
regenerated cellulose. The reactive dyes of the formula (1) are also
suitable for dyeing or printing fibres which contain hydroxyl groups
':
~3~
and which are components of blended fabrics, e.g. of blends of cotton
with polyester or polyamide fibres.
The dyes of this invention can be applied in different manner to the
fibre material and fixed thereon, especially in the form of aqueous
dye solutions and printing pastes. The reactive dyes of formula (1)
are suitable both for the exhaust process and for dyeing by the pad
dyeing process, in which the goods are impregnated with aqueous dye
solutions which may also contain salts, and the dyes are fixed after
treatment with alkali, or in the presence of alkali, with or without
the application of heat. The dyes of this invention are also particu-
larly suitable for the so-called cold pad-batch method, which com-
prises applying the dye together with the alkali on the pad and sub-
sequently fixing the dye by storing the impregnated goods for several
hours at room temperature. After fixation the dyeings or prints are
thoroughly rinsed with cold and hot water, if necessary with the
addition of a compound which acts as a dispersant and promotes the
diffusion of non-fixed dye. The reactive dyes of formula (1) are
also suitable for printing, especially on cotton, and for printing
nitrogen-containing fibres, e.g. wool, silk or blends containing wool.
The reactive dyes of formula (1) are particularly suitable for dyeing
by the exhaust process; the degrees of fixation are high and non-
fixed dye can be readily washed off.
The dyeings and prints obtained with the dyes of this invention on
cellulosic fabrics have excellent tinctorial strength and excellent
dye-fibre bond stability both in aciclic and in alkaline medium, and
they also have good light fastness and very good wetfastness
properties such as fastness to washing, water, sea-water, cross-dyeing
and perspiration, as well as good fastness to pleating, ironing and
rubbing.
~33~3
-- 10 --
The invention is lllustrated by the following Examples in which parts
and percentages are by weight, unless otherwise stated. The ratio of
parts by weight to parts by volume is the same as that of kilograms
to litres,
The preparation of the monoazo or disazo intermediates is not describedin all of the following Examples. However, any undisclosed preparation
is clearly evident from what has been stated above.
Example 1: 21.5 parts of the disazo dye of the formula
IOH ~H2
2 ~ = N ~ N = N - ~/ ~t~ 2
;o~ ;SO H HO S/ ~-/ \o~ ;SO H HO S/ \ ~
are dissolved in 300 parts of ice water to give a neutral solution to
which is added, with good stirring, a solution of 11.4 parts o~
cyanuric chlor;de in 60 parts of acetone. The temperature increases
to 15 to 20~C, while keeping the pH value at 6 to 7 by the dropwise
addition of a solution of l-n sodium hydroxide. When acylation of the
two terminal amino groups is complete, 4 parts of ethanolamine are
added to the dye suspension, the reaction mixture is heated to 40 to
45C and the pH is kept at 8 by the dropwise addition of a solution
of l-n sodium hydroxide. Amidation is complete after 1 to 2 hours.
The dye is precipitated from the resultant solution by adding 10 ~ by
volume of sodium chloride, then isolated by filtration and dried in
vacuo at 60C.
The resultant dye of the formula
i,Cl ~1
2 2 \ ~ 11 i HO S i 11 i so H 11 1 \;~ Z 2
33~9
dyes cotton by the exhaust process in navy blue shades.
Similar dyes are obtained by carrying out the amidation in this
Example replacing ethanolamine by the corresponding amount of one
of the following amines:
CH2CH20H
diethanolamine HN
CH2CH20H
N-methylethanolamine CH3-NH-CH2CH20H
N-ethylethanolamine CH3CH2-NH-CH2CH20H
~CH20H
tris(hydroxymethyl)aminomethane
CH2H
_ .
N-oxethylaniline \ /'-NH-CH2CH20H .
=.
Example 2: A solution of 44 parts of 193-phenylenediamine-4-sulfonic
acid in 250 parts by volume of water and 30 parts of a 30 % solution
of sodium hydroxide are added over about 1/2 hour to a suspension of
44 parts of cyanuric chloride in 250 parts of ice water. The pH
value is subsequently adjusted to 6.5 by slowly adding dropwise a 30 %
solution of sodium hydroxide. As soon as the diamine is no longer
detected, 16 parts of ethanolamine are added to the cold suspension
of the monocondensate. The pH value is kept at 9 to 10.5 by the
addition of a 30 % solution of sodium hydroxide at 10 to 20C. 54
parts by volume of a solution of 4-n sodium nitrite are added to the
resultant solution and diazotisation is effected by running the
mixture into a vessel containing 54 parts of hydrochloric acid in
150 parts by volume of water. Diazotisation is complete within a few
minutes. Any excess nitrite is destroyed with sulfamic acid. A
solution of 31.9 parts of l-amino-8-naphthol-396-disulfonic acid in
150 parts by volume of water and 9 parts of a solution of sodium
3~
- 12 -
hydroxide is then added to this diazo suspension at 10 to 20C.
Coupling is carried out by the addition of a 30% sodium hydroxide
solution or sodi~lm acetate stepwise from pH 2.0 to 3.5, and the
pH is then adjusted to 7Ø
The dye suspension is made up to 1800 parts and the dye is salted
out at 60C by the addition of 9 ~ by volume of sodium chloride.
Further valuable reactive dyes which dye cotton in the shades indicatedin column 4 of Table 1 are obtained by coupling the diazotised diazo
component indicated in column 2 in acid medium to 1-amino-8-hydroxy
naphthalene-3,6-disulfonic acid, and coupling the diazotised diazo
component indicated in column 3 to the monoazo compound so obtained.
- 13 - ~33~
_ ........ . _ -
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- 14 - ~L29~330~
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-- 16 --
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17 -
Dyeing Procedure 1
2 parts of the dye obtained in Example 1 are dissolved at 20 to 50C
in 100 parts of water with the addition of 5 to 20 parts of urea and
2 parts of calcined sodium carbonate. A cotton fabric is impregnated
with this solution to a pick--up of 60 to 80 % and then dried. The
fabric is then thermofixed for 1 1/2 to 5 minutes at 140 to 210C,
subsequently soaped for a quarter of an hour in a 0.1 % boiling
solution of a non-ionic detergent, rinsed and dried.
Dyeing Procedure 2
2 parts of the dye obtained in Example 1 are dissolved at 75C in
2000 parts of water with the addition of 120 parts of sodium chloride
or calcined Glauber's salt. Then 100 parts of a cotton fabric are
put into this dyebath and the temperature is kept constant for 30 to
60 minutes. Then 10 parts of calcined sodium carbonate and 4 ml of
sodium hydroxide solution (36 Bé) are added. The temperature is kept
for a further 45 to 60 minutes at 75 to 80C and the fabric is then
soaped for 15 minutes in a 0.1 % boiling solution of a non-ionic
detergent, rinsed and dried.
Dyeing Procedure 3
2 parts of the dye obtained in Example 1 are dissolved in 100 parts
of water while adding 0.5 part of sodium m-nitrobenzenesulfonate..
A cotton fabric is impregnated with this solution to a liquor pick-up
of 75 % and then dried.
The fabric is then impregnated with a solution of 20C which
contains 5 g/l of sodium hydroxide and 300 g/l of sodium chloride,
and then expresse~ to a pick-up of 75 %. The dyeing is steamed for
30 seconds at 100 to 101C, rinsed, soaped for a quarter of an
hour in a 0.3 % boiling solution of a non-ionic detergent, rinsed
and dried.
~ lo -
Dyeing Procedure 4
-
2 parts of the dye obtained in Example 1 are dissolved in 100 parts
of water. The solution is added to 1900 parts of cold water, 60 parts
of sodium chloride are added and 100 parts of a cotton fabric are
put into this dyebath. The temperature is raised to 60C and 40 parts
of calcined sodium carbonate and another 60 parts of sodium chloride
are added after 30 minutes. The temperature is kept for 30 minutes
at 60C. The dyeing is rinsed and then soaped for 15 minutes in a
0.3 % boiling solution of a non-ionic detergent, rinsed and dried.
Printing Procedure
2 parts of the dye obtained according to Example 1 are sprinkled,
with rapid stirring, into 100 parts of a stock thickening which
contains 45 parts of 5 % sodium alginate thickening, 32 parts of
water, 20 parts or urea, 1 part of sodium m-nitrobenzenesulfonate
and 2 parts of sodium carbonate.
A cotton fabric is printed with the printing paste so obtained on a
roller printing machine. The printed fabric is steamed 4 to 8 mimltes
at 100C in saturated steam, then thoroughly rinsed in cold and hot
water, in the process of which chemically nonfixed dye can be very
easily removed from the fabric, and then dried.
