Reactive disazo dyes

Details Reactive disazo dyes Reactive disazo dyes

2000-06-06

2001-02-20

Powers, Fiona T. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

C534S605000, C534S612000

Reexamination Certificate

active

06191264

ABSTRACT:

This invention relates to disazo dyes containing reactive triazinylamino groups, which disazo dyes include a dyebase having a central 1-hydroxy-8-aminonaphthalenesulphonic acid and terminal respective benzene nuclei each carrying a triazinylamino group.
Such dyes are disclosed, for example, in each of GB-A-2162193, U.S. Pat. No. 5,073,631, EP-A-0122423 and EP-A- 0478504.
Dyes disclosed in U.S. Pat. No. 5,073,631 contain amino groups substituted on each respective triazinyl group, each of which amino groups may be substituted by one or two of optionally substituted alkyl, cycloalkyl, arylalkyl and aryl groups, which optional substituent is selected from a wide range thereof, including carbamoyl. There is a general disclosure of a range of dyes containing a carbamoyl substituted phenyl group. EP-A-0478504 discloses a wide range of dyes, some of which contain amino groups substituted on each respective triazinyl group, each of which amino groups may be substituted by an acylaminoalkyl group. In the dyes of GB-A-2162193 and EP-A-0122423, each triazinyl group is again substituted by an amino group, which may bear any of a wide range of substituents.
We have now found surprisingly that, in such dyes as mentioned above, if at least one triazinylamino group carries on the triazinyl nucleus a carbamoyl alkylamino group, then the resultant dyes have excellent build up, good fastness properties and compatibility with related dyestuffs.
Thus, according to the present invention, there is provided a dye of the formula (I)
wherein:
each R, independently, is R
A
or R
B
,
where RA is a group
in which each of R
1
, R
2
, R
3
and R
4
, independently, is a hydrogen atom or an optionally substituted C
1-4
alkyl group;
R
B
is a group
in which:
R
5
is a hydrogen atom or an optionally substituted C
1-4
alkyl group or an optionally substituted phenyl or naphthyl group;
R
6
is a hydrogen atom or an optionally substituted C
1-4
alkyl group or an optionally substituted phenyl or naphthyl group or is a group NR
5
R
7
;
where R
5
is as defined above; and
R
7
is a hydrogen atom or an optionally substituted C
1-4
alkyl group or is a group of the formula:
COR
5
or CO
2
R
5
where R
5
is as defined above, or
R
5
and R
6
, together with the nitrogen atom to which they are attached, form a ring;
at least one R is a group R
A
;
when each R is R
A
, each R
A
may be the same as or different from the other;
each Y, independently, is a labile atom or group; each of m, n and p, independently is zero, 1 or 2; and
SO
3
M is a sulphonic acid group or salt thereof.
In the above formula, preferably, each R is a group R
A
.
In addition, whether the dye contains one group, or two groups, R
A
, it is preferred that R
A
is:
—N(R
1
)CH(R
2
)CONH(R
3
)
wherein each of R
1
, R
2
and R
3
is as defined above.
Typical preferred examples of R
A
are —NHCH
2
CONH
2
, —NR
8
CH
2
CONH
2
, —NHCH
2
CONHR
8
, —NHCH(R
8
)CONH
2
, —NR
8
CH
2
CONHR
9
, —NR
8
CH(R
9
)CONH
2
, —NHCH(R
8
)CONHR
9
, —NR
8
CH(R
9
)CONHR
10
, more preferably —NR
8
CH
2
CONHR
9
, and even more preferably —NR
8
CH
2
CONHR
8
, where R
8
, R
9
, R
10
are independently optionally substituted C
1-4
alkyl, especially methyl or ethyl.
Where a particular triazinylamino group does not include a group R
A
, then R is a nitrogen-linked group —NR
5
R
6
such as that derived from an alkylamine, an arylamine, or a substituted hydrazine derivative. In alkylamine-derived groups, R
5
and R
6
are independently a hydrogen atom or an optionally substituted C
1-4
alkyl group, or R
5
and R
6
are part of a ring. In arylamine-derived groups, R
5
is as defined above and R
6
is an optionally substituted phenyl or naphthyl group. In hydrazine-derived groups, R
5
is as defined above and R
6
is NR
5
R
7
where R
5
is as defined above and R
7
is a hydrogen atom or optionally substituted C
1-4
alkyl group or is of the formula —COR
5
or —CO
2
R
5
where R
5
is as defined above.
Any alkyl group of R
1
-R
10
is optionally substituted by a C
1-4
alkoxy group such as methoxy, ethoxy, propoxy, isopropoxy or butoxy, a C
2-4
alkanoylamino group such as acetylamino, propionylamino or butyrylamino, a C
1-4
alkoxycarbonyl group such as methoxycarbonyl or ethoxycarbonyl, an amino group optionally substituted by one or two C
1-4
alkyl group(s) such as amino, methylamino, ethylamino, propylamino, isopropylamino or butylamino, a C
1-4
alkylsulphonyl group such as methylsulphonyl or ethylsulphonyl, trifluoromethyl, nitro, cyano, halogen, such as fluorine, chlorine or bromine, carbamoyl, N-(C
1-4
alkyl)carbamoyl such as N-methylcarbamoyl or N-ethylcarbamoyl, sulfamoyl, N-(C
1-4
alkyl)sulfamoyl such as N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl or N-butylsulfamoyl, ureido, hydroxy, carboxy, sulfomethyl or sulfo. Especially preferred such substituents are methoxy, ethoxy, acetylamino, chlorine, bromine, ureido, hydroxy, carboxy, sulfomethyl and sulfo.
By labile atom or group is meant an atom or group which is bound by a chemical bond to the triazine nucleus, which atom or group is displaceable by a hydroxyl group of cellulose under mildly alkaline aqueous conditions to form a covalent bond between the triazine nucleus and cellulose. As examples of such atoms or groups there may be mentioned halogen atoms, for example F and Cl; sulphonic acid groups; thiocyano groups; quaternary ammonium groups, for example trialkylammonium groups and optionally substituted pyridinium groups, for example 3- and 4-carboxy pyridinium groups. A most preferred labile atom is a halogen atom, especially Cl or F.
In the chromophore, the naphthalene nucleus preferably contains two sulphonic acid groups and, more preferably, one such group is at the 3- position and the other is at the 5- or 6-position.
In each of the benzene nuclei A and B, it is preferred that at least one sulphonic acid group or salt thereof is present on each nucleus.
Additionally, as shown in formula (I), each of the benzene nuclei A and B independently is substituted by a substituted triazinylamino group as defined above.
Furthermore, each of nuclei A, B and any phenyl or naphthyl group on R
5
or R
6
, independently, is optionally substituted, for example, by a C
1-4
alkyl group, such as methyl, ethyl, propyl, isopropyl or butyl, a C
1-4
alkoxy group such as methoxy, ethoxy, propoxy, isopropoxy or butoxy, a C
2-4
alkanoylamino group such as acetylamino, propionylamino or butyrylamino, a C
1-4
alkoxycarbonyl group such as methoxycarbonyl or ethoxycarbonyl, an amino group optionally substituted by one or two C
1-4
-alkyl group(s) such as amino, methylamino, ethylamino, propylamino, isopropylamino or butylamino, a C
1-4
alkylsulphonyl group such as methylsulphonyl or ethylsulphonyl, trifluoromethyl, nitro, cyano, halogen, such as fluorine, chlorine or bromine, carbamoyl, N-(C
1-4
alkyl)carbamoyl such as N-methylcarbamoyl or N-ethylcarbamoyl, sulfamoyl, N-(C
1-4
alkyl)sulfamoyl such as N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl or N-butylsulfamoyl, ureido, hydroxy, carboxy, sulfomethyl or sulfo. Especially preferred such substituents are methyl, ethyl, methoxy, ethoxy, acetylamino, chlorine, bromine, ureido, hydroxy, carboxy, sulfomethyl and sulfo.
An especially preferred range of dyes has the formula (II)
wherein R
1
, R
2
and R
3
are as defined above.
A dye of the formula (I) in which each R is a group R
A
can be prepared by a method which comprises:
reacting a dyebase of the formula (III)
wherein SO
3
M, m, n and p are as defined in above, with a triazine of the formula (IV)
where Y is as defined above,
to form a bis-triazinylamino dye of the formula (V)
wherein SO
3
M, m, n, p and Y are as defined above, and then reacting the bis-triazinylamino dye (V)
with a carbamoylalkylamine of the formula (VI)
wherein R
1
, R
2
, R
3
and R
4
are as defined above.
An especially preferred triazine of the formula (IV) is cyanuric chloride or fluoride.
Especially preferred carbamoylalkylamines of the formula (VI) are glycinamide, preferably in the form of

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