Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2001-06-28
2003-04-29
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C008S696000, C008S922000
Reexamination Certificate
active
06555664
ABSTRACT:
The present invention relates to disperse dyes having an N-alkyl-phthalimide-diazo component and an aniline coupling component, to processes for the preparation of such dyes and to the use thereof in dyeing or printing fibre materials, especially polyester-containing fibre materials.
Disperse azo dyes having an N-alkyl-phthalimide-diazo component and an aniline coupling component have been known for a long time and are used in dyeing hydrophobic fibre materials. It has, however, been found that the dyeings or prints obtained using the currently known dyes do not in all cases satisfy today's requirements, especially in respect of fastness to washing and fastness to perspiration. There is therefore a need for new dyes that especially have good washing fastness properties.
It has now been found, surprisingly, that the dyes according to the invention meet the criteria given above to a considerable degree.
The present invention accordingly relates to disperse dyes that yield dyeings having a high degree of fastness to washing and to perspiration and that, in addition, have good build-up characteristics both in the exhaust and thermosol process and in textile printing. The dyes are also suitable for discharge printing.
The dyes according to the invention correspond to formula
wherein
R is methyl or butyl,
R
1
is hydrogen, halogen, cyano or nitro,
R
2
is halogen or cyano,
R
3
is hydrogen, halogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxy,
R
4
is hydrogen, C
1
-C
4
alkyl, halogen, CF
3
or —NHCOR
7
wherein R
7
is C
1
-C
4
alkyl,
R
5
is C
1
-C
6
alkyl that is unsubstituted or substituted by hydroxy, cyano, acyloxy,
or by phenoxy, x being a number from 0 to 4 and it being possible for the alkyl chain, from C
2
upwards, optionally to be interrupted by one or more oxygen atoms, or is a radical of formula —CH
2
CH
2
—O—COR
8
or of formula
and R
6
is a radical of formula —CH
2
CH
2
—O—COR
8
, of formula
or of formula
R
8
and R
9
each independently of the other being C
1
-C
4
alkyl and R
10
being hydrogen or C
1
-C
4
alkyl, or, when R is methyl, R
5
and R
6
are each independently of the other C
1
-C
4
alkyl,
with the proviso that when R is n-butyl and R
5
and/or R
6
is/are a radical of formula —CH
2
CH
2
—O—COR
8
, R
4
may not be chlorine or acetylamino.
R as butyl is n-butyl, iso-butyl, sec-butyl or tert-butyl.
Importance is given to R as methyl or n-butyl, especially methyl.
R
1
and R
2
as halogen are, each independently of the other, for example, fluorine, chlorine or bromine, especially chlorine or bromine, more especially bromine.
R
3
and R
4
as halogen are, each independently of the other, for example, fluorine, chlorine or bromine, especially chlorine or bromine, more especially chlorine.
R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
and R
10
as C
1
-C
4
alkyl are, each independently of the others, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl or tert-butyl, with the following preferences:
As R
3
, preference is given to ethyl or, especially, methyl.
As R
4
, preference is given to ethyl or, especially, methyl.
As R
5
, preference is given to methyl or, especially, ethyl.
As R
6
; preference is given to propyl and, especially, ethyl.
As R
7
, preference is given to ethyl or, especially, methyl.
As R
8
, preference is given to ethyl or, especially, methyl.
As R
9
, preference is given to methyl and, especially, ethyl.
As R
10
, preference is given to methyl.
R
3
as C
1
-C
4
alkoxy is, for example, methoxy, ethoxy, straight-chain or branched propoxy or straight-chain or branched butoxy. Preference is given to ethoxy or, especially, methoxy. A suitable acyloxy substituent in R
5
is, especially, propionyloxy or, more especially, acetoxy.
In the meaning of x preference is given to 2 or, especially, 1.
R
5
as substituted C
1
-C
6
alkyl is especially cyano-substituted C
1
-C
4
alkyl, more especially cyanoethyl.
As R
1
, special preference is given to hydrogen, bromine or cyano, especially hydrogen or bromine.
As R
2
, special preference is given to bromine or cyano, especially bromine.
As R
3
, special preference is given to hydrogen.
As R
4
, special preference is given to hydrogen or —NHCOR
7
, the definition and preferred meanings given above applying to R
7
.
As R
4
, very special preference is given to —NHCOR
7
, the definition and preferred meanings given above applying to R
7
.
As R
5
, special preference is given to ethyl or cyanoethyl.
As R
6
, special preference is given to ethyl or, especially, to the radical —CH
2
CH
2
OCOCH
3
.
As R
6
, special preference is likewise given to the radical
the definitions and preferred meanings given above applying to R
9
and R
10
.
As R
6
, very special preference is given to the radical —CH(CH
3
)—COOC
2
H
5
.
Special preference is given to dyes of formulae
No.
R
1
R
2
R
3
R
4
R
5
R
6
100
—H
—Br
—H
—NHCOCH
3
—C
2
H
5
—CH(CH
3
)COOC
2
H
5
101
—H
—Br
—H
—NHCOC
2
H
5
—C
2
H
5
—CH
2
COOCH
3
102
—H
—Br
—H
—NHCOCH
3
—C
2
H
5
—CH
2
COOC
2
H
5
103
—H
—Br
—H
—NHCOC
2
H
5
—C
2
H
5
—CH(CH
3
)COOCH
3
104
—H
—Br
—H
—NHCOCH
3
—C
2
H
5
—CH
2
COOCH
3
105
—H
—Br
—H
—NHCOC
2
H
5
—C
2
H
5
—CH
2
COOC
2
H
5
106
—H
—Br
—H
—NHCOCH
3
—C
2
H
5
—CH(CH
3
)COOCH
3
107
—H
—Br
—H
—NHCOC
2
H
5
—C
2
H
5
—CH(CH
3
)COOC
2
H
5
108
—H
—Br
—H
—NHCOCH
3
—CH
2
—C
6
H
5
—CH
2
COOCH
3
109
—H
—Br
—H
—NHCOCH
3
—CH
2
CH
2
CN
—CH
2
COOC
2
H
5
110
—H
—Br
—H
—H
—CH
2
CH
2
CN
—CH
2
CH
2
OCOCH
3
111
—H
—NO
2
—H
—NHCOCH
3
—C
2
H
5
—CH
2
COOCH
3
112
—Br
—NO
2
—H
—NHCOCH
3
—C
2
H
5
—CH
2
COOCH
3
113
—CN
—NO
2
—H
—NHCOCH
3
—C
2
H
5
—CH(CH
3
)COOC
2
H
5
114
—H
—Br
—H
—NHCOCH
3
—CH
2
COOCH
3
—CH(CH
3
)COOC
2
H
5
115
—H
—Br
—H
—NHCOCH
3
—CH
2
COOC
2
H
5
—CH(CH
3
)COOCH
3
116
—H
—Br
—OCH
3
—NHCOCH
3
—C
2
H
5
—CH(CH
3
)COOC
2
H
5
117
—H
—CN
—H
—NHCOCH
3
—C
2
H
5
—CH(CH
3
)COOC
2
H
5
118
—H
—CN
—H
—NHCOCH
3
—C
2
H
5
—CH(CH
3
)COOCH
3
119
—H
—Br
—Cl
—NHCOCH
3
—C
2
H
5
—CH(CH
3
)COOC
2
H
5
120
—CN
—CN
—H
—NHCOCH
3
—CH
2
COOCH
3
—CH(CH
3
)COOC
2
H
5
121
—CN
—CN
—H
—NHCOCH
3
—C
2
H
5
—CH(CH
3
)COOC
2
H
5
122
—H
—CN
—H
—NHCOCH
3
—CH
2
COOCH
3
—CH(CH
3
)COOC
2
H
5
123
—Br
—Br
—H
—NHCOCH
3
—C
2
H
5
—CH(CH
3
)COOC
2
H
5
124
—Br
—Br
—H
—NHCOCH
3
—C
2
H
5
—C
2
H
5
125
—H
—Cl
—H
—NHCOCH
3
—C
2
H
5
—CH(CH
3
)COOC
2
H
5
126
—H
—Br
—H
—NHCOCH
3
—C
2
H
5
—CH
2
CH
2
COOCH
3
Special preference is likewise given to dyes of formulae
No.
R
4
R
5
R
6
127
—NHCOCH
3
—C
2
H
5
128
—H
—CH
3
Special preference is likewise given to dyes of formulae
No.
R
1
R
2
R
3
R
4
R
5
R
6
129
—H
—Br
—H
—NHCOCH
3
—C
2
H
5
—CH(CH
3
)COOC
2
H
5
130
—H
—Br
—H
—H
—C
2
H
5
—CH
2
CH
2
OCOCH
3
131
—H
—Br
—H
—H
—C
2
H
5
—CH
2
CH
2
CN
132
—H
—Br
—H
—H
—CH
2
CH
2
CN
—CH
2
CH
2
OCOCH
3
133
—H
—Br
—H
—H
—C
2
H
5
—CH
2
COOCH
3
134
—H
—Br
—H
—H
—C
2
H
5
—CH
2
COOC
2
H
5
135
—H
—Br
—H
—H
—C
2
H
5
—CH(CH
3
)COOC
2
H
5
136
—H
—Br
—H
—H
—C
2
H
5
—CH(CH
3
)COOCH
3
137
—H
—Br
—H
—H
—CH
2
CH
2
CN
—CH
2
—C
6
H
5
138
—H
—Br
—H
—H
—CH
2
CH
2
CN
—CH
2
CH
2
CN
139
—H
—Br
—H
—H
—CH
2
CH
2
OCOCH
3
—CH
2
CH
2
OCOCH
3
140
—H
—CN
—H
—NHCOCH(CH
3
)
2
—C
2
H
5
—CH
2
COOC
2
H
5
141
—H
—Br
—H
—NHCOCH
3
—C
2
H
5
—CH(CH
3
)COOCH
3
Very special preference is given to dyes of formulae
The present invention relates also to the process for the preparation of the dyes of formula (1) according to the invention.
The dyes are prepared, for example, by nitration of a phthalimide of formula
in the acid range, as described, for example, on page 459 in Organic Synthesis, Collective Volume 2, (a Revised Edition of Annual Volumes X-XIX), J. Wiley & Sons, followed by alkylation of the resulting nitro compound, for example in accordance with a method described in Journal of Organic Chemistry 32 (1967) on page 1923, paragraph 3, and, for example after reductive treatment described in Bull. Soc. Chim. de France 1957 on page 569, conversion into an intermediate of formula
wherein R has the definition and preferred meanings given above.
Using generally known methods, the intermediate of formula (51) is, in an acid medium, nitrated or mono- or poly-halogenated—it being possible, if desired, for the halogen substituents t
Arquint Alfons
Clement Antoine
Dreier Romeo
Lauk Urs
Ciba Specialty Chemicals Corporation
Mansfield Kevin T.
Powers Fiona T.
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