Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2001-07-24
2003-09-23
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C534S605000, C534S612000, C534S638000, C534S642000, C008S549000
Reexamination Certificate
active
06624291
ABSTRACT:
DESCRIPTION
Yellow-Reactive Monoazo Dyes Containing a Tertiary or a Quarternary Nitrogen Group, Methods for Their Preparation and Use Thereof for Dyeing Hydroxy- and/or Carboxamido-Containing Fiber Material
The present invention relates to the field of fiber-reactive dyes.
Yellow reactive dyes are known from U.S. Pat. No. 5,456,727, EP 141367, 395951, 486176, 623655, 630946, 632107 and 647683. However these dyes have some deficiencies, such as poor color build-up or unsatisfactory staining behaviour of the dyeings.
With the present invention, yellow dyes of improved properties conforming to the general formula (1) have unexpectedly been found, which produce dyeings in very good color yields with excellent color build-up and consistent shade. Additionally the dyeings obtained using the inventive dyes surprisingly show no or very little staining on polyamide fibers.
The present invention provides yellow dyes conforming to the general formula (1):
wherein
Y is vinyl or is ethyl which is substituted in the &bgr;-position by a substituent which can be eliminated by the action of an alkali, forming the vinyl group, such as chlorine, thiosulfato, sulfato, alkanoyloxy of 2 to 5 carbon atoms, such as acetyloxy, phosphate, sulfobenzoyloxy and p-toluylsulfonyloxy, and is preferably vinyl, &bgr;-chloroethyl, &bgr;-thiosulfatoethyl or &bgr;-sulfatoethyl and is in particular vinyl or &bgr;-sulfatoethyl;
M is hydrogen or an alkali metal, such as lithium, sodium or potassium;
X is fluorine, chlorine, amino, C
1
to C
4
alkoxy, such as methoxy, ethoxy, propyloxy, butyloxy, or is phenoxy, or phenylamino, which may be substituted by halogen or sulfo, mono- or dialkyl amine, with C
1
to C
4
alkyl, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, which may be substituted further by sulfo, sulfato or hydroxy groups, preferably amino or methoxy or fluoro and is in particular chlorine;
R
1
is hydrogen, methyl, methoxy or a group of the formula SO
3
M, preferably methoxy and in particular hydrogen;
R
2
has one of the meanings of R
1
;
Q is cyanamido or is a group of the formula (a) or (b)
wherein
A is hydrogen, C
1
to C
6
alkyl such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, pentyl or hexyl, preferably C
1
to C
4
alkyl groups, in particular methyl and ethyl, which may be substituted by hydroxy, sulfo or sulfato or is phenyl which may be substituted by one or more halogens such as chloro, fluoro or bromo, by acetamido- or by sulfo and is preferably 4-chlorophenyl and in particular 3-metanilic or 2,5-dimetanilic acid;
B has one of the meanings of A and is preferably hydrogen, methyl or ethyl;
D has one of the meanings of A; or the group of the formula
(a) is a cyclic ringsystem such as morpholino, piperidino or piperazino, in particular morpholino, or prolino;
(b) is a cyclic ringsystem such as N-methyl morpholinium or N-ethyl morpholinium, N-ethyl piperidinium, or is a bicyclic ringsystem such as 1,4-diaminobicyclo (2,2,2)octyl, or is pyridinium which may be substituted by carboxy, such as 3-carboxy-pyridinium or 4-carboxy-pyridinium, or by carboxamido, such as 3-carboxamidopyridinium, and is in particular 3-carboxy-pyridinium;
n is 0 if Q is a group of the formula (a) and n is 1 if Q is a group of formula (b);
W
−
is a halogenide or the equivalent of a divalent anionic group such as sulfate or carbonate and is preferably chloride or fluoride;
The groups “sulfo”, “thiosulfato”, “carboxy”, “phosphato” and “sulfato” include both the acid form and the salt form of these groups. Accordingly, sulfo groups are groups of the formula —SO
3
M, thiosulfato groups are groups of the formula —S—SO
3
M, carboxy groups are groups of the formula —COOM, phosphato groups are groups of the formula —OPO
3
M
2
and sulfato groups are groups of the formula —OSO
3
M, in which M is defined as above.
The dyes of the general formula (1) can have, within the meaning of Y, structurally different fiber-reactive groups —SO
2
—Y. In particular, the fiber reactive groups —SO
2
—Y are partly vinylsulfonyl groups and partly groups in which Y is a &bgr;-ethyl substituted group as defined above, such as &bgr;-chloroethylsulfonyl, &bgr;-thiosulfatoethylsulfonyl or, preferably, &bgr;-sulfatoethylsulfonyl groups. If the dye contains the respective dye component in the form of a vinylsulfonyl dye, the proportion of the respective vinylsulfonyl dye to the respective dye with Y being a &bgr;-ethyl substituted group as defined above, such as a &bgr;-chloro- or &bgr;-thiosulfato- or &bgr;-sulfatoethyl-sulfonyl dye, will be up to about 30 mol-%, based on the respective dye chromophore. Preference is given to the dyes in which the proportion of vinylsulfonyl dye to said &bgr;-ethyl substituted dye, such as &bgr;-sulfatoethylsulfonyl dye is in terms of the molar ratio between 5:95 and 30:70.
The dyes of the invention can be present as a preparation in solid or liquid (dissolved) form. In solid form they generally contain the electrolyte salts customary in the case of water-soluble and in particular fiber-reactive dyes, such as sodium chloride, potassium chloride and sodium sulfate, and also the assistants customary in commercial dyes, such as buffer substances capable of establishing a pH in aqueous solution between 3 and 7, such as sodium borate, sodium bicarbonate, sodium citrate, sodium dihydrogenphosphate and disodium hydrogenphosphate, small amounts of siccatives or, if they are present in liquid, aqueous solution (including the presence of thickeners of the type customary in print pastes), substances which ensure the permanence of these preparations, for example mold preventatives.
If the dyes take the form of dye powders, they contain, as a rule, 10 to 50% by weight, based on the dye powder or preparation, of a strength-standardizing colorless diluent electrolyte salt, such as those mentioned above. These dye powders may in addition contain the abovementioned buffer substances in a total amount of up to 5%, based on the dye powder. If the dyes of the invention are present in aqueous solution, the total dye content of these aqueous solutions is up to about 75% by weight, the electrolyte salt content of these aqueous solutions preferably being below 10% by weight, based on the aqueous solutions (liquid preparations) and they can in general contain the abovementioned buffer substances in an amount of up to 10% by weight, preferably up to 5% by weight.
The dyes of the invention can be obtained in a conventional manner, for instance by synthesis by means of customary diazotization and coupling reactions in a manner familiar to those skilled in the art using appropriate substituted phenylamine derivatives conforming to the general formula (2)
wherein Y is a alkali eliminable group and R
1
and R
2
are as defined above, and coupling components, such as diaminophenylsulfonic acid in the necessary proportions to give the diazo component of the general formula (3).
wherein R
1
, R
2
and Y are as defined above.
Reacting this intermediate at pH 9,5-1,5 with cyanuric halogenide gives the azo dye conforming to the formula (4):
wherein X is fluorine or chlorine, and by reaction with a compound of the general formula Q′ at pH 2-9 eventually under heating wherein Q′ is a group of the formula:
in which
A, B, D and n are as defined above to give a claimed dyestuff of the formula (1a):
with X, Y, W, n, Q′, R
1
and R
2
as defined above, and subsequent introduction of X by substitution reaction in conventional manner if X is different of fluorine and chlorine.
The resulting dyestuff can be isolated from the solution in the conventional manner, for example by salting out with an electrolyte salt, such as sodium chloride or potassium chloride, or by spray-drying.
Dye components in form of the vinylsulfonyl dye can be prepared by the above mentioned method using appropriate vinylsulfonyl starting anilines, or alternately by reacting the dye mixture in which Y is a &bgr;-chloroethyl, &bgr;-thiosulfatoethyl, or &bgr;-sulfatoethyl radical with alka
Connolly Bove & Lodge & Hutz LLP
DyStar Textilfarben GmbH & Co. Deutschland KG
Powers Fiona T.
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