Hydroxypyridonemethide azo dyes

Details Hydroxypyridonemethide azo dyes Hydroxypyridonemethide azo dyes

2002-12-04

2003-09-30

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C008S639000, C008S662000

Reexamination Certificate

active

06627742

ABSTRACT:

The invention relates to novel hydroxypyridonemethide azo dyes, processes for their preparation and their use and also dye mixtures containing hydroxypyridonemethide azo dyes. EP-A 767 220 already discloses similar azo dyes. These dyes, however, are still in need of improvement with regard to their application properties, especially their thermomigration fastness.
Novel hydroxypyridonemethide azo dyes have been found that, surprisingly, are notable for excellent thermomigration fastness and sublimation fastness coupled with good general fastnesses.
The present invention provides novel hydroxypyridonemethide azo dyes conforming to the formula (I) or its tautomeric forms
where
X
1
is H, Cl, Br, —CN, —CH═O, —CO—T, —CO
2
—R
2
, —SO
2
—T, or —NO
2
,
X
2
, X
3
and X
4
are independently H, Cl or Br,
R
1
is H, T, or —CF
3
, and
R
2
is straight-chain or branched C
1
-C
4
-alkyl,
where
T is straight-chain or branched C
1
-C
10
-alkyl which may be interrupted by 1 or 2 oxygen atoms in ether function and/or substituted by one or more, preferably one, phenyl or hydroxyl radicals, or is phenyl which may be substituted by 1 to 2 identical or different radicals selected from the group consisting of Cl, Br and C
1
-C2-alkyl.
The dyes of the formula (I) can also exist in tautomeric forms, of which the most important is the formula (Ia)
For the purposes of the present invention, the formula (I) in its general and preferred meanings includes all possible tautomeric forms, especially that of the formula (Ia).
Preference is given to hydroxypyridonemethide azo dyes of the formula (I) or (Ia) where
X
2
, X
3
and X
4
are each H.
Particular preference is given to dyes of the formulae (I) and (Ia), where
X
2
, X
3
and X
4
are each H,
R
1
is H, —CH
3
, —C
2
H
5
, —CH(CH
3
)
2
, unsubstituted phenyl or CF
3
, and
R
2
is CH
3
or C
2
H
5
.
Very particular preference is given to dyes of the formula (I) where
x
1
is H, Cl, Br, or —NO
2
,
X
2
, X
3
and X
4
are each H,
R
1
is H, —CH
3
, —C
2
H
5
, or —CH(CH
3
)
2
, and
R
2
is CH
3
or —C
2
H
5
.
Preference is given in particular to dyes of the formula (I) where
X
1
is nitro,
X
2
, X
3
and X
4
are each H,
R
1
is H or CH
3
, and
R
2
is CH
3
or C
2
H
5
.
The dyes of the invention may be prepared, for example, by diazotizing an amine of the formula (II)
where
X
1
, X
2
, X
3
and X
4
are each as defined above,
and coupling it onto a coupling component of the formula (III)
where
R
1
and R
2
are each as defined above and
E is a substituent that is displaceable by electrophilic substitution, preferably by H, —CO
2
H, —CH
2
OH, —SO
3
H, —CH═O, —COT, —CONH
2
, —CONHT,
and where T is as defined above.
Such a coupling process by displacement of a substituent is described for example in GB-A 2036 775 and JP-A 58 157 863.
The coupling reaction may be carried out in aqueous and nonaqueous solvents. Nonaqueous solvents are alcohols such as methanol, ethanol, propanol, butanol, pentanol, etc., dipolar aprotic solvents such as DMF, DMSO, NMP and water-immiscible solvents such as toluene or chlorobenzene.
The coupling is preferably carried out in a stoichiometric ratio of coupling component and diazo component, although it may be advantageous and sensible, partly for economic reasons, to use the cheaper component in an excess of up to 30%.
The coupling is generally effected at temperatures between −30 to 100° C., preference being given to temperatures of −10 to 30° C., and particular preference to temperatures of −5 to 10C.
The coupling may be carried out in an acidic as well as an alkaline medium. Preference is given to pH <10, particular preference to pH <7.0, very particular preference to pH <5.0.
The diazo components of the formula (II) are literature known and partly also, like the particularly preferred 3-nitro-4-aminophenol, commercially available.
The coupling components of the formula (III) are likewise known and their preparation is described for example in EP-A 767 220.
The dyes of the formula (I) according to the invention are useful as such, mixed with each other or else mixed with other disperse dyes for dyeing and printing, including by the inkjet process, hydrophobic synthetic fiber materials and their blends with natural fiber materials.
Useful hydrophobic synthetic materials include for example secondary cellulose acetate, cellulose triacetate, polyamides and particularly polyesters, for example polyethylene glycol terephthalate. Examples of useful natural fiber materials are cotton, regenerated cellulose fibers and wool.
The dyes of the invention or mixtures thereof are also useful for coloring and printing waxes, oils and plastics such as polymethacrylate, PVC, polystyrene or ABS.
They are also useful for textile and nontextile thermal transfer printing, for example by means of a thermal head.
The coloring, dyeing and printing conditions, which include dyeing in supercritical carbon dioxide, are known per se, cf. for example EP-A 827 988, DE-A 3508 904 and EP-A 474 600.
The dyes of the invention or mixtures thereof can also be used for dyeing keratinic fibers, for example in hair dyeing or in the dyeing of furs.
The novel dyes of formula (I) or their mixtures are further very useful for producing color filters as described for example in EP-A-399 473.
Finally they are also useful as colorants for preparing toners for electrophotography.
The dyes of the invention or the mixtures thereof dye polyester in orange to violet shades having excellent thermomigration fastness and sublimation fastness, high color strength and a bright hue.
Particularly good affinity and build-up is provided by mixtures of the dyes of formula (I) which contain two or more, preferably two to 4, different dyes of the formula (I). Preference is given to mixtures which differ in the R
1
and/or R
2
substituents.
The present invention further provides dye mixtures containing at least one dye of the formula (I) and also at least one further disperse dye. Useful disperse dyes are the disperse dyes listed in the Color Index, especially benzodifuranone dyes, and also the disperse dyes known from EP-A 767 220.
Benzodifuranone dyes which are preferentially suitable as mixture dyes are derived from the formula (IV)
where
Y
1
and Y
2
are independently H, C
1
-C
6
-alkoxy, with or without C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxy-C
2
-C
4
-alkoxycarbonyl or furfuryl substitution, —OC
2
H
4
—O—C
1
-C
4
-alkyl or —OC
2
H
4
—O—(C
2
H
4
O)
1-6
—C
1
-C
4
-alkyl.
Of these, the following may be mentioned in particular:
(IVa) Y
1
=OCH
2
CH
2
CH
3
, Y
2
=H
(IVb)
 Y
2
═H
(IVc) Y
1
=OCH
2
CH
2
CH
3
, Y
2
=OCH
2
CO
2
C
2
H
4
OC
2
H
5
(IVd) Y
1
=H, Y
2
=OCH
2
CO
2
C
2
H
4
OC
2
H
5
Preference is given to dye mixtures containing at least one dye of the formula (I) and at least one dye of the formula (IV).
Preference is further given to dye mixtures containing at least one dye of the formula (I) and at least one disperse dye of the formula (V)
where
D is the radical of a carbo- or heterocyclic diazo component,
A
1
and A
2
are independently H or a typical pyridone substituent,
A
5
is H, a radical of the formula T, —OT
1
, —NH
2
, —NHT, —NT
2
, —NHCOH, —NHCOT, —N═CH—T,—N═CT
2
or —NHSO
2
T,
or
A
1
and A
2
and/or
A
2
and A
3
and/or
A
4
and A
5
combine with the atoms in between in each case to form an unsaturated, substituted or unsubstituted 5- or 6-membered carbo- or heterocycle, with the proviso that in the event of ring formation by participation of one of A
3
and A
4
the nonparticipant radical is an electron-attracting radical,
X is O, NH, NT, NCOT, NCO
2
T or NSO
2
T,
A
3
and A
4
are independently —CN, —CO
2
T, —CONH
2
, —CONHT, —CONT
2
, CF
3
, —CHO, —COT, —SO
2
T, —SO3T
4
, —SO
3
T
5
, SO
2
NH
2
, SO
2
NHT, SO
2
NT
2
, —SOT, —CH═NH, —CH═NT, —CT═NH, —CT═NT,
 —CO—CO
2
T, —NO
2
, —NO, or T
4
T
5
but A
3
and A
4
are preferably not both T
4
and/or T
5
or
A
3
and A
4
combine with the carbon atom to which they are attached to form a cyc

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