Bridged disazo compounds

Details Bridged disazo compounds Bridged disazo compounds

2000-03-27

2002-04-02

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S689000, C534S797000, C106S031480, C008S681000, C008S918000, C008S919000

Reexamination Certificate

active

06365719

ABSTRACT:

BACKGROUND OF THE INVENTION
The invention relates to monoazo compounds containing sulphonic acid groups, salts thereof and mixtures of these compounds. They are suitable for use as dyestuffs.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
According to the invention there are provided compounds of formula (I):
wherein
D is the rest of a diazo component selected from the group having the formulae (a), (b), (c)
A is OH or NH
2
;
R
1
is independently H, C
1-4
alkyl;
R
2
is hydrogen, C
1-4
alkyl, C
1-4
alkoxy, halogen;
X is an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group;
Y is a divalent bridge;
m is 0, 1 or 2; and
n is 1 or 2;
and salts thereof as well as mixtures of such compounds.
Preferred compounds of formula (I) have the formulae (Ia), (Ib) or (Ic):
wherein R
1
, R
2
, X, Y and A have the meaning given above; in metal-free or copper complex form, and salts thereof and mixtures of such compounds or complexes. Preferably the compounds of formula (Ia) above, are in metal-free form.
wherein R
1
, R
2
, m, n, X and Y have the meaning given above;
wherein R
1
, R
2
, X and Y have the meaning given above; salts thereof and mixtures of such compounds.
Preferably the sulphonic acid groups on the naphtholrest are attached at the 3- and 6-positions of the naphthol radical.
Any alkyl or alkylene present is linear or branched unless indicated to the contrary. In any hydroxy- or alkoxy-substituted alkyl or alkylene group which is linked to a nitrogen atom, the hydroxy or alkoxy group is bound to a carbon atom other than to the C
1
-atom. In any alkylene group substituted by two hydroxy groups, the hydroxy groups are bound to different carbon atoms.
Halogen atoms are preferably chlorine.
X is preferably amino, mono- or di-C
1-3
alkylamino, mono- or di(hydroxy-C
2-4
alkyl)amino, monocarboxy-C
1-4
alkylamino, monosulpho-C
1-4
alkylamino, optionally substituted phenylamino, phenylalkylamino, morpholino or piperazino (substituted by alkyl or hydroxyalkyl).
Y is a divalent bridge linking two parts of the molecule via nitrogen atoms attached to the triazine ring and preferably is the rest of phenylene diamine, piperazine or 4,4′-diaminostilbene-2,2′-disulfonic acid.
Any alkyl as R
1
preferably contains 1 or 2 carbon atoms, and is more preferably methyl. Any substituted alkyl is preferably linear or branched C
2-3
alkyl, and is preferably monosubstituted by hydroxy.
R
2
is preferably hydrogen or C
1-4
alkyl, most preferably methyl.
The present invention further provides a process for the preparation of compounds of formula (I) comprising reacting the dyestuff of formula (IIa) having the following formula:
in which R
1
is as above defined and Hal is halogen, with a diazotised compound of formula (IIb), having the following formula:
D—NH
2
  (IIb)
so as to give a compound of formula (III), having the following formula:
in which D and R
1
are as above defined, which compound is reacted with an appropriate diamino compound to give a compound of formula (I) in which X is halogen.
Finally, such compound is further reacted with an appropriate amino compound to give a compound of formula (I) in which X is an amino group. If mixtures are intended, the starting compounds are reacted as mixtures or the final compounds are mixed.
An alternative process for the preparation of compounds of formula (I), in which D is of formula (a) with A=OH and/or formula (c), comprises reacting the dyestuff of formula (IV) having the following formula:
in which D and R
1
are as above defined and preferably the substituents being so positioned as above defined, with cyanuric halogenide so as to give a compound of formula (III), having the following formula:
in which D and R
1
are as above defined, which compound is reacted with an appropriate diamino compound to give a compound of formula (I) in which X is halogen. Finally, such compound is further reacted with an appropriate amino compound to give a compound of formula (I) in which X is an amino group.
A metal-free compound of formula (I) in which D is of the formula (a) with COOH may be converted into a 1:1 copper complex in accordance with known methods. This coppering may be carried out by reacting an appropriate metal-free compound of formula (I) with a copper-donating compound which is employed in such an amount so as to provide at least one equivalent of copper per equivalent of monoazo compound to be metallised.
Suitably, the 1:1 copper complexes may be prepared at 10° C. to 50° C. and at pH 4 to 7 in the presence of copper(II) salts.
The compounds of formula (I) thus obtained may be isolated in accordance with known methods.
The type of cations assigned to the sulpho groups in a compound of formula (I) may be influenced in various ways in accordance with the process; these are known methods throughout. In particular, mixed salts may be obtained by well-directed control of the process employed.
The compounds according to the invention in the form of their water-soluble salts are used for dyeing or printing organic substrates containing hydroxy groups, thiol groups or nitrogen, in particular as paper dyes or direct dyes.
As a result of their high substantivity, the compounds according to the invention are very suitable as direct dyes. The usual technical application processes are employed as dyeing and printing processes. Natural and regenerated cellulose, e.g. cotton, are preferably dyed by a conventional exhaust process at dyeing temperatures of 50-100° C.
The dyestuffs according to the invention are notable for their depth of color, and produce good exhaust. The dyeings obtained (especially on cotton and paper) are of pure shade.
On the said substrates, the dyeings generally have very good wet fastnesses and good light fastness. The very good water and perspiration fastness and good fastness to peroxide, perborate and chlorine may also be mentioned.
The wet fastness of the direct dyeings on cellulosic textile materials may be decisively improved by means of a special after-treatment with selected assistants. In particular, the washing fastness is improved such that its quality level does not undergo any reduction even after repeated washes at 60° C.
A suitable assistant for this after-treatment may be a fixing agent in the form of a pre-condensate or mixture, which is obtained either
A) from the product of reacting the mono- or poly-functional primary or secondary amine with cyanamide, dicyandiamide, guanidine or biguanide; or of ammonia with cyanamide or dicyandiamide, whereby the product contains reactive hydrogen atoms bonded to nitrogen, or
B) from a quaternary polyalkylene-polyamine with
C) a N-methylol compound of a urea, melamine, guanamine, triazinone, urone, carbamate or acid diamide, optionally in the presence of
D) a catalyst for cross-linking with a N-methylol compound of type C.
Details relating to the assistant in the form of the combination A/C/D are described in detail in PCT application publication no. WO 81/02 423; details on the combination B/C/D may be found in German Published Specification DOS 31 37 404.
Printing is effected by means of impregnation with a printing paste which is prepared by a known method.
The new dyestuffs may also be used for dyeing or printing leather, preferably chrome-tanned types of leather, using methods known per se. In addition, the dyestuffs may be used to produce inks by a method known per se.
Most preferably, the dyestuffs are used for dyeing or printing of paper e.g., sized or unsized, wood-free or wood-containing paper or paper-based products such as cardboard. They may be used in continuous dyeing in the stock, dyeing in the size press, in a conventional dipping or surface coloring process. The dyeing and printing of paper is effected by known methods.
The dyeings and prints and particularly those obtained on paper, show good fastness properties.
The compounds of formula (I) may be converted into dyeing preparations. Processing into stable liquid, preferably aqueous, or solid (granulated or powder form) dyeing preparations may take place in a generally kn

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