Azo disperse dye mixtures

Details Azo disperse dye mixtures Azo disperse dye mixtures

2001-09-13

2004-01-27

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dye or potential dye composition, additive, treatment,...

Mixed dyes, noncomplexed

C008S638000, C008S922000

Reexamination Certificate

active

06682573

ABSTRACT:

This invention relates to mixtures of disperse azo dyes.
A known azo dye is C.I. Disperse Orange 37 of the formula
This dye is disclosed, for example, in CH-A-0406481. Commercially, the dye has been mixed with other dyes to give different shades. However, this dye has been found to act as a skin irritant.
Mixtures of azo dyes are also disclosed in DE-A-4304744 and BE-A-0592096.
DE-A-4304744 discloses dye mixtures containing
(a) 10 to 90 wt % of one or more azo dyes of the formula
 wherein Y
1
is absent or is C
1-6
alkyl, C
1-6
alkoxy or optionally substituted C
1-8
alkylamino or C
3-4
alkenylamino and each of Y
2
and Y
3
independently is hydrogen or optionally substituted C
1-6
alkyl;
(b) 10 to 90 wt % of (b
1
) an azo dye component of the formula
 and optionally (b
2
) an azo dye component of the formula
 in which dye component (b
1
) is present in an amount of 50 to 100 wt %, and dye component (b
2
) is present in an amount of 0 to 50 wt %, of component (b); and
(c) 0 to 70 wt % of one or more azo dyes of the formula (c
1
) or (c
2
)
 in which R
c
1
is a nitro or C
1-6
alkylsulphonyl group optionally substituted by hydroxy;
each of R
c
2
and R
c
3
independently is absent or is chlorine or bromine;
each of R
c
4
and R
c
5
independently is absent or is chlorine;
each of R
c
6
and R
c
7
independently is hydrogen or is an optionally substituted C
1-4
alkyl or phenyl group or when R
c
2
and R
c
3
are absent or are chlorine, R
c
6
and R
c
7
may additionally be cyanoethyl.
BE-A-0592096 discloses dyes of the formula
wherein
X
D
is hydrogen* or is chlorine, bromine, cyano, trifluoromethyl or nitro.
Y
D
is hydrogen*, chlorine, bromine or low molecular weight alkyl;
U
D
exemplified as hydrogen* or methyl (no other definition given);
Z
D
is hydrogen* or low molecular weight alkyl;
R
D
1
is low molecular weight alkyl, alkoxyalkyl or acyloxyalkyl;
m
D
is zero or 1;
n
D
is zero or 1; and
the value of R
D
2
is such that when n
D
is zero and m
D
is 1, R
D
2
is acyloxyalkyl while when m
D
is zero and n
D
is 1, R
D
2
is cyanoethyl.
BE-A-0592096 also discloses mixtures of dyes of the above formula (d) in which, specifically n
D
is zero, m
D
is 1, Y
D
is NHCOCH
3
and R
D
2
is acyloxyalkyl with dyes of the formula (e)
wherein
V
E
is hydrogen*, chlorine or bromine;
W
E
is chlorine, bromine, cyano or trifluoromethyl;
R
E
4
is hydrogen*, methyl, ethyl or chlorine; and
R
1
is low molecular weight alkyl, alkyloxyalkyl or acyloxyalkyl.
* Although BE-A-0592096 refers to “hydrogen” as being a possible substituent for each of U
D
, X
D
, Y
D
, Z
D
, V
E
and R
E
4
, it seems clear that this is intended merely to indicate the absence of such a substituent.
It is pointed out that there is no disclosure, in BE-A-0592096, of dyes of the formula (e) wherein each of V
E
and W
E
is a chlorine or bromine atom and R
E
1
is a low molecular weight alkyl group.
Surprisingly, we have found a range of dye mixtures in which the components do not cause any noticeable skin irritation and which provide at least one of excellent heat fastness, high colour strength and excellent build-up characteristics.
Thus, the present invention provides a dye mixture comprising at least
(1)
(A) at least one azo dye of the formula (I)
 wherein
each of X and X
1
independently is chlorine or bromine;
R
1
is absent or is C
1-4
alkyl; and
each of R
2
and R
3
independently is hydrogen, C
1-6
alkyl or cyanoethyl; but
when R
1
is absent, R
2
is n-butyl or cyanoethyl and R
3
is cyanoethyl; and
(B) at least one azo dye of the formula (II)
 wherein
X
2
is absent or is chlorine or bromine;
each of R
4
and R
5
independently is hydrogen, C
1-4
alkyl, allyl or cyloxyalkyl;
R
6
is C
1-4
alkyl or NHCOY, in which Y is hydrogen, C
1-4
alkyl, or NH
2
; and
R
7
is C
1-4
alkoxy; and
at least when, in the formula (I), R
1
is absent and, in the formula (II), X
2
is bromine, R
6
is NHCOY (in which Y is methyl), R
7
is methoxy and each of R
4
and R
5
is allyl or one of R
4
and R
5
is allyl and the other is hydrogen
(C) at least one azo dye of the formula (III)
 wherein
X
3
is absent or is chlorine or bromine;
R
8
is C
1-4
alkyl or NHCOY, in which Y is hydrogen, C
1-4
alkyl or NH
2
; and
each of R
9
and R
10
independently is hydrogen, C
1-4
alkyl, allyl or acyloxyalkyl; or
(2)
(A) at least one azo dye of the formula (I), given and defined above, wherein R
1
is absent, R
2
is n-butyl or cyanoethyl and R
3
is cyanoethyl; and
(D) at least one azo dye of the formula (IV)
 wherein
R
11
is absent or is C
1-4
alkyl;
R
12
is hydrogen, cyano, hydroxyl, OCOR
14
or OCOOR
14
in which R
14
is C
1-4
alkyl, aryl or aralkyl;
R
13
is hydroxyl, OCOR
14
in which R
14
is as defined above; and each of m and n independently is 1, 2, 3 or 4.
Alkyl groups may be straight-chained or branched and be for example methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec. butyl or tert.-butyl. This applies as well to alkyl groups in acyloxyalkyl, alkoxy and aralkyl residues. Acyl in acyloxyalkyl is preferably COY wherein Y is C
1-4
alkyl. Aryl is preferably phenyl and naphthyl. Aralkyl is preferably benzyl and phenethyl.
In one preferred range of dye mixtures embodying the invention, the dye of the formula (I) has the formula
in which each of X and X
1
independently is chlorine or bromine and R
2
is n-butyl or cyanoethyl, and the mixture additionally contains a dye of the formula (II), given and defined above and optionally a dye of the formula (III), also given and defined above.
In such a dye mixture, an especially preferred dye of the formula (I)
1
has the formula (1)
Such a dye does not cause irritation to the skin and lends to the mixture excellent heat fastness.
Especially when the mixture contains a dye of the formula (I)
1
, given and defined above, a preferred dye of the formula (II) in the mixture has the formula (II)
1
in which X
2
is chlorine or bromine and R
7
is methoxy or ethoxy.
It is not necessary to include, in a mixture containing the dyes of the formulae (I)
1
and (II)
1
, a dye of the formula (III) but such a dye may be added when a different shade is required.
A dye mixture of dye components of the respective formulae (I)
1
and (II)
1
preferably contains from 15-75% inclusive of the dye of the formula (I)
1
and from 25-85% inclusive of the dye of the formula (II)
1
, more preferably from 30-60% inclusive of the dye of the formula (I)
1
and from 40-70% inclusive of the dye of the formula (II)
1
, by weight of the weight of the mixture of dyes of the formulae (I)
1
and (II)
1
.
On the other hand, when, in a dye mixture containing dye components of the formula (II)
1
a dye of the formula (III) is additionally present, this dye component preferably has the formula (III)
1
in which X
3
is chlorine or bromine, Y is methyl or ethyl and each of R
9
and R
10
independently is ethyl or allyl.
In such a dye mixture, the dye of the formula (II) is preferably a dye (II)
2
in which X
2
is chlorine, each of R
4
and R
5
independently is ethyl, allyl or acetoxyethyl, R
6
is the group NHCOY (in which Y is methyl or ethyl) and R
7
is C
1-6
alkoxy.
In an especially preferred dye mixture embodying the invention in the formula (I)
1
, R
1
is absent, R
2
is n-butyl, R
3
is cyanoethyl and each of X and X
1
is chlorine; in the formula (II), X
2
is bromine, R
6
is the group NHCOY (in which Y is methyl), R
7
is methoxy and each of R
4
and R
5
is allyl; and, in the formula (III)
1
, X
4
is bromine, R
8
is the group NHCOY (in which Y is methyl) and each of R
9
and R
10
is ethyl.
A dye mixture containing each of dye components of the respective formulae (I)
1
, (II) and (III)
1
preferably contains, by weight of the weight of the mixture of dyes of the formulae (I)
1
, (II) and (III)
1
,
from 5-50% inclusive of the dye of the formula (I);
from 5-75% inclusive of the dye of the formula (II); and
from 5-75% inclusive of the dye of the formula (III);
and more preferably
from 5-25% inclusive of the dye of the formula (I);
f

Affiliated with

Also associated with

Rating

Azo disperse dye mixtures does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Azo disperse dye mixtures, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Azo disperse dye mixtures will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3190651