US 2003/0191293 A1 · Reactive dyes containing a halobenzene nucleus

Abstract

The invention relates to reactive dyes containing a halobenzene nucleus and, in particular, reactive dyes containing a halobenzene nucleus and two or more reactive components.

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Claims83

Dependent claims

A dye containing

at least one chromophore D;
at least a first, halobenzene, reactive group Z1, of the formula (I)
353
in which:
n is 1 or 2
X, or each X independently, is an electron withdrawing group;
and
Y is a halogen atom;
at least a second reactive group Z2 selected from
(1) a group of the formula (I), given and defined above, but selected independently thereof;
(2) a group of the formula (II)
354
wherein
m is 1 or 2;
p is 0 or 1;
when m is 1, p is 1;
and when m is 2, p is 0;
Y1, or each Y1 independently, is a halogen atom or an optionally substituted pyridinium group;
and
T is C1-4alkoxy, C1-4thioalkoxy or N(R1) (R2), in which each of R1 and R2 independently is hydrogen, optionally substituted C1-4alkyl or optionally substituted aryl;
(3) a group of the formula (III)
355
wherein:
x is 1, 2 or 3;
y is zero, 1 or 2;
and
x+y≦3;
Y2, or each Y2 independently, is a halogen atom or an optionally substituted pyridinium group;
and
U or each U independently, is C1-4alkyl or C1-4alkylsulphonyl;
(4) a group of the formula (IV)
—SO2CH2CH2X1 (IV)
wherein
X1 is an eliminatable group;
(5) a group of the formula (V)
—SO2(CH2)zCH═CH2 (V)
wherein
z is zero or 1;
and
(6) a group of formula (VI)
—W—C(R10)═CH2 (VI)
wherein:
R10 is hydrogen, C1-4alkyl or halogen;
and
W is —OC(═O)— or —N(R11)C(═O)— in which R11 is hydrogen or C1-4 alkyl;
at least a first linking group L1, linking the said first, halobenzene, reactive group Z1 to one of components (i) the or a chromophore D and (ii) the second reactive group Z2, which said first linking group L1 presents an amino nitrogen to the reactive group Z1 and to the component (i) or (ii) or, when component (i) contains a heterocyclic nitrogen atom, is linked directly to the nitrogen atom and which said first linking group L1 optionally includes a hydrocarbon bridging group, which hydrocarbon bridging group B has at least two carbon atoms, is optionally substituted, optionally includes at least one hetero atom and is optionally a chromophore;
and
when Z2 is selected from the said groups (I)-(III), at least a second linking group L2 linking the second reactive group Z2 to one of (i) the or a chromophore D and (ii) the said first reactive group Z1, which said linking group L2 is selected from
(1) a linking group L1, but selected independently thereof;
or
(2) an amide linkage;
and
(3) a sulphonamide linkage;
and optionally at least one aromatic group Ar which, when Z2 is selected from the said groups (IV)-(VI), may carry the said reactive group Z2.

51 more elements

A dye according to any preceding claim, of the formula (VIII)

Z1-L1-D-(L2)a-Z2 (VIII)
wherein:
D is a chromophore;
each of L1 and L2 is an amine or piperazine linkage of the formula
—N(R)— (VII)1;
357 —N(R)BN(R)— (VII)3
wherein:
R, or each R independently, is hydrogen or C1-4 alkyl;
B is a hydrocarbon bridging group which has at least two carbon atoms, is optionally substituted, optionally includes at least one hetero atom and is optionally a chromophore;
a is zero or 1;
and
b is from 2 to 6 inclusive;
Z1 is a group
358
in which:
n is 1 or 2;
X, or each X independently, is an electron withdrawing group;
and
Y is a halogen atom;
and
when a is 1, Z2 is:
a group of the formula (I), given and defined above but selected independently thereof;
or
a group of the formula (II)
359
wherein:
m is 1 or 2;
p is 0 or 1;
when m is 1, p is 1;
and when m is 2, p is 0;
Y1, or each Y1 independently, is a halogen atom or an optionally substituted pyridinium group;
and
T is C1-4 alkoxy, thioalkoxy or N(R1) (R2) in which R1 is hydrogen, optionally substituted C1-4 alkyl or optionally substituted aryl and
R2 is hydrogen or optionally substituted C1-4 alkyl;
or
a group of the formula (III)
360
wherein:
x is 1, 2 or 3;
y is zero, 1 or 2;
and x+y≦3;
Y2, or each Y2 independently, is a halogen atom;
and
U, or each U independently, is C1-4 alkyl or C1-4 alkylsulphonyl;
and
when a is zero, Z2 is:
—SO2CH2CH2X1 (IV)
in which
X1 is an eliminatable group;
or
—SO2(CH2)zCH═CH2 (V)
wherein
z is zero or 1;
or
a group of formula (VI)
—W—C(R10)═CH2 (VI)
wherein:
R10 is hydrogen, C1-4alkyl or halogen;
and
W is —OC(═O)— or —N(R11)C(═O)— in which R is hydrogen or C1-4 alkyl.

57 more elements

Dependencies are inferred from the claim text.

Description10,015 words

Summary6,470 words

#This invention relates to reactive dyes containing a halobenzene nucleus and, in particular, reactive dyes of this type containing two or more reactive components.

#Dyes are known which contain a halobenzene nucleus linked via an azo group to another aromatic nucleus such that the halobenzene nucleus forms part of the chromophoric chain (see for example GB-A-882001). Dyes of this type which contain two such halobenzene nuclei are disclosed in CA64,14316d (1966), which is an English language abstract of an article by Matsui et al, Yuki Gosei Kagaku Kyokai Shi(1966), 24-(2), 132-136.

#Dyes are also known in which the halobenzene nucleus is attached to a chromophoric group by a sulphonamide or amide linkage; see, for example, GB-A-978162 and CA59,12949g (1963), which is an English language abstract of an article by Matsui et al in Yuki Gosei Kagaku Kyokai Shi (1962), 20,1100-1112. Again dyes of this type may contain two such halobenzene nuclei; see GB-A-978162.

Detailed description3,545 words

#2-amino-4-(N-acetyl)aminobenzene-1-sulphonic acid (0.5M, 182 g) was dissolved in water (600 ml) at pH 7 and 2M sodium nitrite solution added (0.526M, 263 ml). This solution was added dropwise to a mixture of hydrochloric acid 35% (1.13M, 100 ml, SG=1.18) and ice (1 Kg), maintaining a temperature of 0-5° C. The mixture was stirred for 0.5 hrs with excess nitrous acid at 0-5° C. A solution of sulphamic acid (10%) was added to remove excess nitrous acid to obtain a suspension of a diazotized diamine for coupling.

#H-Acid (0.475M, 183 g) was dissolved in water (800 ml) at pH 7.5. This solution was added dropwise to the above diazo suspension with good agitation over 1 hr at 0-2° C. The mixture was then stirred at 0-2° C. for a further 2 hrs at pH 2-3, and allowed to warm to room temperature over 18 hrs.

#The viscous suspension was adjusted to pH 6 using sodium hydroxide solution (46/48%) and a solution of a monoazo dye was thereby obtained.

Reactive dyes containing a halobenzene nucleus

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Reactive dyes containing a halobenzene nucleus

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Life of this patent

Abstract

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Claims83

Description10,015 words

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Classification4 codes

Life of this patent

Description10,015 words