Bleaching and dyeing; fluid treatment and chemical modification – Synthetic fiber dyeing – Polyamide fiber
Reexamination Certificate
2000-08-24
2003-04-29
Ogden, Necholus (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Synthetic fiber dyeing
Polyamide fiber
C008S924000, C008S641000, C008S643000
Reexamination Certificate
active
06554874
ABSTRACT:
The present invention relates to a method for the trichromatic dyeing or printing of natural and synthetic polyamide fibre materials.
The problem underlying the present invention was to find a method of dyeing or printing natural and synthetic polyamide fibre materials using dyes suitable for combination according to the trichromatic principle.
The dyeing or printing of natural and synthetic polyamide fibre mat rials according to the trichromatic principle is known. It has, however, been found that the resulting dyeings do not always fully meet the highest demands, especially in respect of brilliance and fastness to wetting and light. There is therefore a need for new dyes that can bell used in a trichromatic dyeing technique and that yield dyeings or prints which exhibit very good fastness to wetting and/or light.
It has now been found that the problem can be solved according to he invention by the method described hereinbelow. The dyeings so obtained meet the Objectives set. In particular, the dyeings obtained are distinguished by uniform colour build-up and, at the same time, constancy of shade at different concentrations and by good combinability, as well as by good fastness to wetting properties and good fastness to light,
The present invention relates to a method for the trichromatic dyeing or printing of natural or synthetic polyamide fibre material, which method comprises using at least one blue-dyeing dye of formula
wherein
X is halogen, hydroxy, C
1
-C
4
alkoxy, S—C
1
-C
4
alkyl, —NHR
1
, —NHR
1
R
2
, morpholino, piperidino or azepano, R
1
being unsubstituted or hydroxy- or carboxy-substituted C
1
-C
4
alkyl, and R
2
being unsubstituted or hydroxy-, sulfo-, carboxy- or phenyl-substituted C
1
-C
4
alkyl or phenyl,
W is —NR
3
— or —O—, R
3
being hydrogen or C
1
-C
4
alkyl,
A and B are each independently of the other a cycloaliphatic or aromatic bridge member,
Q
1
and Q
2
are each independently of the other an anthraquinone radical, and
z is an integer 2, 3 or 4, together with at least one red-dyeing dye of formula
wherein
R and R′ are each independently of the other hydrogen or unsubstituted or substituted
C
1
-C
4
alkyl,
R
5
, R
6
, R
7
and R
8
are each independently of the others hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy,
C
2
-C
4
alkanoylamino, ureido, halogen or sulfo, and
X
1
is halogen, hydroxy, C
1
-C
4
alkoxy, S—C
1
-C
4
alkyl, —NHR
1
, —NR
1
R
2
, morpholino, piperidino or azepano, R
1
being unsubstituted or hydroxy- or carboxy-substituted C
1
-C
4
alkyl, and R
2
being unsubstituted or hydroxy-, sulfo-, carboxy- or phenyl-substituted C
1
-C
4
alkyl or phenyl, and together with at least one yellow- or orange-dyeing dye of formula
or of formula
wherein
R and R′ are each independently of the other hydrogen or unsubstituted or substituted C
1
-C
4
alkyl,
X
2
and X
3
are each independently of the other halogen, hydroxy, C
1
-C
4
alkoxy, S—C
1
-C
4
alkyl, —NHR
1
, —NR
1
R
2
, morpholino, piperidino or azepano, R
1
being unsubstituted or hydroxy- or carboxy-substituted C
1
-C
4
alkyl, and R
2
being unsubstituted or hydroxy-, sulfo-, carboxy- or phenyl-substituted C
1
-C
4
alkyl or phenyl, and
R
9
, R
10
, R
11
, R
12
, R
13
, R
14
, R
15
and R
16
are each independently of the others hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, ureido, halogen, sulfo, or C
2
-C
4
alkanoylamino or C
1
-C
4
alkoxycarbonylamino each of which is unsubstituted or substituted in the alkyl moiety.
The trichromatic principle is understood to refer to the additive colour mixing of appropriately selected yellow- or orange-, red- and blue-dyeing dyes, by means of which it is possible to obtain any desired shade of the visible colour spectrum by suitably selecting the relative proportions of the dyes.
C
1
-C
4
Alkyl that comes into consideration for R, R′, R
1
, R
2
, R
3
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, R
12
, R
13
, R
14
, R
15
and R
16
is, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, with preference being given to methyl or ethyl, especially methyl. Radicals R and R′ as C
1
-C
4
alkyl may be unsubstituted or substituted, for example by hydroxy, C
1
-C
4
—alkoxy, halogen or by sulfato, but are preferably unsubstituted.
C
1
-C
4
Alkoxy that comes into consideration for R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, R
12
, R
13
, R
14
, R
15
, R
16
and X is, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy or tert-butoxy, especially methoxy.
C
2
-C
4
Alkanoylamino that comes into consideration for R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, R
12
, R
13
, R
14
, R
15
and R
16
is, for example, propionylamino or, especially, acetylamino. Radicals R
9
, R
10
, R
11
, R
12
, R
13
, R
14
, R
15
and R
16
as C
2
-C
4
alkanoylamino may be unsubstituted or substituted, for example, in the alkyl moiety by C
1
-C
4
alkoxy or by hydroxy.
C
1
-C
4
Alkoxycarbonylamino that comes into consideration for R
9
, R
10
, R
11
, R
12
, R
13
, R
14
, R
15
and R
16
is especially methoxy- or ethoxy-carbonylamino. Radicals R
9
, R
10
, R
11
, R
12
, R
13
, R
14
, R
15
and R
16
as C
1
-C
4
alkoxycarbonylamino may be unsubstituted or substituted, for example, in the alkyl moiety by C
1
-C
4
alkoxy or by hydroxy.
S—C
1
-C
4
alkyl that comes into consideration for X, X
1
, X
2
and X
3
is, for example, methylthio, ethylthio, propylthio or butylthio.
Halogen that comes into consideration for R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, R
12
, R
13
, R
14
, R
15
, R
16
, X, X
1
, X
2
and X
3
is, for example, fluorine or bromine and, especially, chlorine.
A is preferably a cyclohexylene or phenylene radical.
B is preferably a cyclohexylene or phenylene radical.
W is preferably a radical of formula —NR
3
—.
X
1
, X
2
and X
3
are preferably fluorine or chlorine, especially chlorine.
R and R′ are preferably, each independently of the other, hydrogen or C
1
-C
4
alkyl, especially hydrogen.
R
3
is preferably hydrogen.
R
5
, R
6
, R
7
and R
8
are preferably, each independently of the others, hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, ureido or halogen, especially hydrogen.
R
9
, R
10
, R
11
, R
12
, R
13
, R
14
, R
15
and R
16
are preferably, each independently of the others, hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, ureido, halogen, or C
2
-C
4
alkanoylamino or C
1
-C
4
alkoxycarbonylamino each of which is unsubstituted or substituted in the alkyl moiety by C
1
-C
4
—alkoxy or by hydroxy.
As blue-dyeing dye there is preferably used at least one dye of formula
wherein
X′ is —Cl, —OH, —N(CH
2
CH
2
OH)
2
, —N(CH
3
)(CH
2
CH
2
SO
3
H), —NHCH
2
COOH, —N(CH
2
CH
2
CH
2
CH
3
)
2
,
A′ is a cyclohexylene or phenylene radical and
B′ is a cyclohexylene or phenylene radical.
As blue-dyeing dye there is especially used the dye of formula
As blue-dyeing dye there is also especially used the dye of formula
As red-dyeing dye there is preferably used at least one dye of formula
wherein R, R′, R
5
, R
6
, R
7
, R
8
and X
1
have the definitions and preferred meanings given above.
Especially preferred red-dyeing dyes are those of formula (2), more especially those of formula (8), wherein
R and R′ are each independently of the other hydrogen or C
1
-C
4
alkyl, especially hydrogen,
R
5
, R
6
, R
7
and R
8
are each independently of the others hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy,
C
2
-C
4
alkanoylamino, ureido or halogen, especially hydrogen, and
X
1
is fluorine or, especially, chlorine.
As red-dyeing dye there is more especially used a dye of formula
The yellow- or orange-dyeing dyes of formulae (3) and (4) preferably contain in the naphthalene rings, in each case, only one or two sulfo groups, and especially, in each case, only one sulfo group. The total number of sulfo groups of the dyes of formulae (3) and (4) is preferably in each case from two to four, especially two.
Preferred yellow- or orange-dyeing dyes of formula (3) are those of formula
wherein R, R′, R
9
, R
10
, R
11
, R
12
and X
2
have the definitio
Adam Jean-Marie
Bacher Jean-Pierre
Elhilo Eisa
Ogden Necholus
LandOfFree
Method of dyeing or printing polyamide-containing materials does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Method of dyeing or printing polyamide-containing materials, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of dyeing or printing polyamide-containing materials will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3109535