Fiber-reactive disazo compounds

Details Fiber-reactive disazo compounds Fiber-reactive disazo compounds

2001-03-14

2002-10-01

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S637000, C534S582000

Reexamination Certificate

active

06458936

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to fiber-reactive disazo compounds of formula (I) and a process for their production and the use of these compounds in dyeing or printing processes. These compounds are suitable for use as fiber-reactive dyestuffs in any conventional dyeing or printing processes.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The invention provides compounds of formula (I)
and salts thereof, or mixtures of such compounds or of their salts, wherein
X is a group —CH═CH
2
or —CH
2
CH
2
Y, wherein Y is —OH or a group which can be split off under alkaline conditions,
R
1
is H, —SO
3
H, —COOH, —OCH
3
, or —CH
3
,
R
2
is C
1-4
alkyl or C
1-4
hydroxyalkyl,
Z is —Cl or —F.
In preferred compounds according to formula (I) Y is —OSO
3
H, —Cl or —SSO
3
H.
In further preferred compounds according to formula (I) R
1
is —H or —SO
3
H.
In further preferred compounds according to formula (I) R
2
is —CH
3
, —CH
2
CH
3
or —CH
2
CH
2
OH.
In more preferred compounds according to formula (I) Y is —OSO
3
H.
In more preferred compounds according to formula (I) R
1
is —H.
In more preferred compounds according to formula (I) R
2
is —CH
3
or —CH
2
CH
3
.
Especially preferred compounds of formula (I) correspond to formula (Ia)
wherein R
2
is —CH
3
or —CH
2
CH
3
and Z is —Cl or —F and salts thereof and mixtures thereof.
When a compound of formula (I) is in salt form, the cation associated with sulpho, sulfato and any carboxy groups 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 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)
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) are obtained by reaction of 2,4-diaminobenzenesulfonic acid with the condensation product of the appropriate amino starting material with 2,4,6-trifluoro- or 2,4,6-trichlorotriazine.
The condensation reaction of the amino compound with 2,4,6-trifluorotriazine is carried out in a manner known per se, preferably at −10° to 10° C., more preferably at −5° to 0° C., and at a pH of about 4-7. The condensation reaction of the amino compound with or 2,4,6-trichlorotriazine 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 4-7.
The diazotization 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.
The compounds of formula (I) and mixtures thereof are useful as fiber-reactive dyestuffs for dyeing or printing on 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 on hydroxy group- or nitrogen-containing organic substrates. Preferred substrates are paper, 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 substrates are paper and textile material comprising cotton.


REFERENCES:
patent: 4649193 (1987-03-01), Meininger et al.
patent: 5243034 (1993-09-01), Tappe et al.
patent: 0 374 758 (1990-06-01), None
patent: 59-174652 (1984-10-01), None
patent: 60-099170 (1985-06-01), None
patent: 09-328627 (1997-12-01), None
International Search Report for PCT/IB 01/00355, mail dateOct. 17, 2001.
English abstract for JP 59-174652, Oct. 3, 1984.

Affiliated with

Also associated with

Rating

Fiber-reactive disazo compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Fiber-reactive disazo compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fiber-reactive disazo compounds will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2980662