Reactive monoazo dyestuffs and the processes in which they are p

Details Reactive monoazo dyestuffs and the processes in which they are p Reactive monoazo dyestuffs and the processes in which they are p

1997-01-14

1998-05-05

Powers, Fiona T.

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

Organic compounds

Azo

534638, C09B 6251, D06P 138

Patent

active

057476578

DESCRIPTION:

BRIEF SUMMARY
THIS APPLICATION IS A 371 OF PCT/EP95/02779 FILED JUL. 14, 1995.

The objects of the invention are monoazo dyestuffs which contain reactive groups, processes for their production and their use as reactive dyes in dyeing and printing processes.
The invention relates to dyestuffs of formula I ##STR2## their salts or mixtures thereof, wherein ##STR3## X signifies hydrogen or chlorine, Z signifies a group --CH=CH.sub.2, --CH.sub.2 CH.sub.2 W or mixtures thereof wherein W is a leaving group removable by alkali and --SO.sub.2 --Z may be bonded in a meta- position with respect to the azo group when RG is of formula (i) and --SO.sub.2 --Z may be bonded in a meta- or para-position with respect to the azo group when RG is of formula (ii) or formula (iii).
R.sub.1 preferably signifies hydrogen, R.sub.2 preferably signifies NHCONH.sub.2 or NHCOCH.sub.3, W, preferably is a leaving group such that upon removal of W-H by alkali a group --CH=CH.sub.2 remains and is more preferably a sulphuric acid ester, a thiosulphuric acid ester, a phosophoric acid ester, an acetic acid ester or a halogen, e.g., bromine, chlorine or iodine, most prerferably the sulphuric acid ester group --OSO.sub.2 OH and --SO.sub.2 --Z is preferably bonded at a meta position, more preferably the 5-position to the azo group.
The most preferred dyestuffs according to the invention are according to the formula ##STR4## and their salts, wherein RG represents ##STR5## R.sub.1 is hydrogen, R.sub.2 is NHCONH.sub.2 or NHCOCH.sub.3 and the reactive sulphonic acid radical, --SO.sub.2 --(CH.sub.2).sub.2 --O--SO.sub.2 -OH, is in the 5- position or RG represents ##STR6## R.sub.1 is hydrogen, R.sub.2 is NHCONH.sub.2 or NHCOCH.sub.3, X is defined as above and the reactive sulphonic acid radical, --SO.sub.2 --(CH.sub.2).sub.2 --O--SO.sub.2 --OH, is in the 5- position or RG represents ##STR7## R.sub.1 is hydrogen, R.sub.2 is NHCONH.sub.2 and the reactive sulphonic acid radical, --SO.sub.2 --(CH.sub.2).sub.2 --O--SO.sub.2 --OH, is in the 5- position.
The invention provides in another of its aspects a process for the production of dyestuffs of formula I, their salts or mixtures thereof, which comprises the step of reacting a compound of formula II ##STR8## with a compound selected from ##STR9##
The process is preferably carried out at a temperature of from 10.degree. to 80.degree. C., preferably 20.degree. to 60.degree. C. and at a pH of from 4 to 7. Advantageously, the process is carried out in an aqueous medium.
In an alternative process according to the invention dyestuffs of formula I, their salts or mixtures thereof, wherein RG represents ##STR10## are prepared by reacting a compound of formula II ##STR11## with Cyanuric fluoride and thereafter reacting the reaction product with morpholine. The process is advantageously carried out in an aqueous medium. The reaction of a compound II with cyanuric fluoride is carried out at a temperature of between 0.degree. and 5.degree. C. with a slight excess of cyanuric fluoride. The resultant product is reacted with a slight excess of morpholine at a temperature of between 0.degree. to 20.degree. C.
The compounds of formula II are conveniently obtained, when a compound of formula IV ##STR12## is diazotised and coupled with a coupling component of formula V ##STR13##
The diazotisation reaction is carried out according to a conventional synthesis and is preferably carried out at a temperature of between 0.degree. to 10.degree. C., more preferably 0.degree. to 5.degree. C. and at a pH of from 0 to 2. The coupling reaction is likewise conventional and may be preferably carried out at a temperature of 5.degree. to 25.degree. C. and at a pH of from 0.5 to 4.
The starting materials of formulae IV and V are conventional and readily available or easily prepared from commonly available reagents using conventional syntheses.
In a preferred process according to the invention the group Z is represented by the formula --CH.sub.2 CH.sub.2 --O--SO.sub.2 --OH.
Dyestuffs of formula I may be isolated from the reaction mixture according to known m

Affiliated with

Also associated with

Rating

Reactive monoazo dyestuffs and the processes in which they are p does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Reactive monoazo dyestuffs and the processes in which they are p, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Reactive monoazo dyestuffs and the processes in which they are p will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-56166