Fiber-reactive disazo dyestuffs

Details Fiber-reactive disazo dyestuffs Fiber-reactive disazo dyestuffs

2000-02-18

2001-09-04

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S637000, C008S549000, C106S031470

Reexamination Certificate

active

06284876

ABSTRACT:

This invention relates to fiber-reactive disazo compounds and a process for their production. These compounds are suitable for use as fiber-reactive dyestuffs in any conventional dyeing or printing processes.
More particularly, the invention provides compounds of formula (I)
and salts thereof, or a mixture of such compounds or salts, in which
X
1
is —SO
2
Z,
X
2
is —NRQ,
Z is a group —CH═CH
2
or —CH
2
CH
2
Y in which Y is a group which can be split off under alkaline conditions,
R is hydrogen, C
1-4
alkyl or C
1-4
hydroxyalkyl
Q is
Preferred meanings of Y are —OSO
3
H, —Cl and —SSO
3
H, especially preferred is —OSO
3
H.
Preferably, R is hydrogen.
More preferred compounds of formula (I) correspond to formula (Ia)
and salts thereof.
Preferably, the —SO
3
H group is in 3 position.
Preferably, the —SO
2
Z group is in 4 position.
When a compound of formula (I) is in salt form, the cation associated with the sulpho groups and any carboxy group is not critical and may be any one of those non-chromophoric cations conventional in the field of fiber-reactive dyes provided that the corresponding salts are water-soluble. Examples of such cations are alkali metal cations and unsubstituted and substituted ammonium cations, e.g., lithium, sodium, potassium, ammonium, mono-, di- and tri-ethanolammonium.
The preferred cations are the alkali metal cations and ammonium, with sodium and potassium being the most preferred.
In a compound of formula (I) the cations of the sulpho groups can be the same or different, e.g., they can also be a mixture of the above mentioned cations meaning that the compound of formula (I) can be in a mixed salt form.
The invention further provides a process for the preparation of compounds of formula (I) or mixtures thereof which is characterized by coupling a compound of formula (II)
with a diazotized amine of formula (III)
wherein X
1
is the rest —SO
2
Z and X
2
is —NRQ, and optionally compounds with the rest —SO
2
CH
2
CH
2
Y are converted to compounds with the rest —SO
2
CH═CH
2
.
Compounds of formula (II) are obtained by diazotisation and coupling of appropriate amines with an 1-amino-8-hydroxynaphthalene disulfonic acid.
Compounds of formula (III) carrying the rest —NRQ are obtained by condensation of the appropriate starting material with 2,4,6-trifluoro- or 5-chloro-2,4,6-trifluoropyrimidine.
The condensation reaction of the amino compound with 2,4,6-trifluoropyrimidine or 5-chloro-2,4,6-trifluoropyrimidine is carried out in a manner known per se, preferably at 0° to 50° C., more preferably at 10° to 20° C., and at a pH of about 5-7.
The diazotisation and coupling reactions are effected in accordance with conventional methods; coupling is preferably carried out at 5° to 30° C., the first coupling to a compound of formula (II) in an acidic medium at a pH of 0 to 4, the second coupling to a compound of formula (I) in a weakly acidic to weakly basic reaction medium at a pH of 4 to 9.
The compounds of formula (I) may be isolated in accordance with known methods, for example, by conventional salting out with an alkali metal salt, filtering and drying optionally in vacuum and at slightly elevated temperatures.
Depending on the reaction and isolation conditions, a compound of formula (I) is obtained in free acid or preferably salt form or even mixed salt form containing, for example, one or more of the above mentioned cations. It may be converted from free acid to a salt form or mixture of salt forms or vice versa or from one salt form to another by conventional means.
It should be noted that any group Q which is a pyrimidinyl radical with a floating fluoro substituent according to the formula
can occur in two isomeric forms where the floating fluoro substituent is bound either to the 2- or to the 6-position.
In general, it is preferred to use this mixture as it is without resorting to the isolation of a single isomer for use, but should this be desired it can be readily achieved by conventional methods.
The compounds of formula (I) and mixtures thereof are useful as fiber-reactive dyestuffs for dyeing or printing hydroxy group- or nitrogen-containing organic substrates. Preferred substrates are leather and fiber material comprising natural or synthetic polyamides and, particularly, natural or regenerated cellulose such as cotton, viscose, lyocell fibers and spun rayon. The most preferred substrate is textile material comprising cotton.
Dyeing or printing is effected in accordance with known methods conventional in the fiber-reactive dyestuff field. Preferably, for the compounds of formula (I) the exhaust dyeing method is used at temperatures within the range of 30° to 100° C., particularly at 40°-80° C., respectively, whereby a liquor to goods ratio of 6:1 to 30:1 is used and more preferably of 10:1 to 20:1.
The compounds of this invention have good compatibility with known fiber-reactive dyes; they may be applied alone or in combination with appropriate fiber-reactive dyestuffs of the same class having analogous dyeing properties such as common fastness properties and the extent of ability to exhaust from the dyebath onto fiber. The dyeings obtained with such combination mixtures have good fastness properties and are comparable to those obtained with a single dyestuff.
The compounds of formula (I) give good exhaust and fixation yields when used as dyestuffs. Moreover, any unfixed compound is easily washed off the substrate. The dyeings and prints derived from the compounds of formula (I) exhibit good light fastness and good wet fastness properties such as wash, water, seawater and sweat fastness. They also exhibit good resistance to oxidation agents such as chlorinated water, hydrochloride bleach, peroxide bleach and perborate-containing washing detergents.
The new dyestuffs can also be used in the preparation of printing inks which are suitable for the ink jet process.
The following examples illustrate the invention. In the examples all parts and percentages are by weight unless indicated to the contrary, and all temperatures are given in degrees Centigrade.


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