Fiber reactive dyestuffs

Details Fiber reactive dyestuffs Fiber reactive dyestuffs

2000-02-08

2001-12-11

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S618000, C534S622000, C534S635000, C534S636000, C534S637000, C534S638000, C534S642000

Reexamination Certificate

active

06329514

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to reactive dyestuffs, in particular relates to novel fiber reactive dyestuffs suitable for use in dyeing hydroxy or amino containing fibers, especially fiber materials containing cellulose.
BACKGROUND OF THE INVENTION
Fiber reactive dyestuffs have been known for many years. Their main characteristic is that they possess one or more reactive groups which can be reacted with hydroxy or amino containing fiber materials to form a covalent bond. For example, U.S. Pat. Nos. 4,703,112, 5,484,899, and G.B. Pat. No. 1,353,899 disclose fiber reactive dyestuffs which are applied by exhaust, printing or continuous dyeing.
SUMMARY OF THE INVENTION
The present invention relates to novel fiber reactive dyestuffs of the formula (I)
wherein:
Z is hydrogen atom or —N═N—Z
1
, wherein Z
1
is
wherein
X is fluorine atom, chlorine atom, hydroxyl, carboxypyridinium such as 3-carboxypyridinium, C
1-4
alkoxyl, —NHCN,
 N,N-di-&bgr;-hydroxyethylamino, amino, amino derivatives such as substituted amino, or phenylamino which is substituted —SO
2
(CH
2
)
2
OSO
3
HSO
3
H, SO
3
H, Cl, COOH, C
1-4
alkyl, or alkoxyl;
Y is —OH, —CH
2
═CH
2
or —CH
2
—CH
2
—W, W is a leaving group which is eliminable by a base;
I is —SO
3
H, C
1-4
alkoxyl, C
1-4
alkyl or C
1-4
alkoxycarbonyl;
P is 0, 1, 2, or 3;
Q is —SO
2
—Y, —CONH—(CH
2
)
n
—SO
2
—Y, —O—(CH
2
)
m
—CONH—(CH
2
)
n
—SO
2
—Y, or —NH—CO—T, wherein Y is defined as the above, T is &agr;,&bgr;-dihalopropionyl or &agr;-haloacryloyl, m and n each independent is 1, 2, 3, 4, 5, or 6;
D
2
is
 wherein I, p, Q, and Y are defined as the above;
R is hydrogen atom, C
1-4
alkyl, or C
1-4
alkyl which is substituted by halogen atom, hydroxyl, cyano, C
1-4
alkoxyl, C
1-4
alkoxycarbonyl, carboxyl, sulfonyl, or sulfato;
D is hydrogen atom or
wherein X and R are defined as the above; only one of D and Z maybe a hydrogen atom. That is, if D is hydrogen Z is —N═N—Z
1
; if Z is hydrogen D is
D
1
is a chromophore with or without reactive groups, wherein said reactive groups are selected from the above Q group, said chromophore is selected from the group consisting of:
(a) formazan chromophore
wherein p is 0, 1, 2, or 3, o is 0, 1, 2, or 3;
(b) anthraquinone
wherein G is an arylamine or (cyclo) alkylene group which is substituted by C
1-4
alkyl or sulfonyl;
(c) phthalocyanine
wherein Pc is copper phthalocyanine or nickel phthalocyanine; W is —OH or —NH
2
; E is arylene such as phenylene or alkylene such as ethylene; o is defined as the above;
(d) triphendioxazine
E is defined as the above;
(e) monoazo
wherein
R
1
is C
1-4
alkyl, C
1-4
alkoxyl, hydroxyl, carboxyl, sulfonyl, or —SO
2
—Y, Y is defined as above;
R
2
is C
1-4
alkyl, C
1-4
alkoxyl, amino, acetylamino, ureido, or sulfonyl;
R
3
is C
1-4
acyl or benzoyl;
R
4
is C
1-4
alkyl or carboxyl;
R
5
and R
6
are C
1-4
alkyl; R
7
is hydrogen, carbonamido, sulphomethyl or methyl sulfonic acid;
m, n, o and p is defined as the above;
(f) polyazo
wherein R
8
is C
1-4
alkyl, C
1-4
alkoxyl, carboxyl, sulfonyl, acetyl, acetylamino, ureido, or —SO
2
—Y;
q, r, s, t and u is each independently is 0, 1, 2 or 3;
R
1
, Y, m, n, o and p are defined as above; or
(g) a metallized monoazo or diazo dye.
The preferred examples of D
1
H are as below:
For convenience sulphonic acid groups are depicted as free acids. More usually they exists in the form of water-soluble salts, especially alkali metal salts, alkaline earth metal salts, ammonium salts or substituted ammonium salts, and, more preferably, lithium salts, sodium salts, potassium salts, ammonium salts or triethanolamine salts.
The dyestuffs of formula (I) of the present invention can be synthesized by known preparation methods. There is no special limit to synthetic steps. Examples of synthetic methods are:
a) The diazonium salt derived from Z
1
—NH
2
is coupled with 4-amino-2-(2-carboxyethyl)amino benzene sulfonic acid to yield compounds of following formula (II).
wherein Z
1
is defined as the above.
b) 4-amino-2-(2-carboxy ethyl) amino benzene sulfonic acid is condensed with the halotriazine of formula (A), then the reaction product is condensed with D
1
—NHR wherein D
1
and R are defined as above to yield compounds of formula (III). Furthermore, it is possible to alter the reaction sequence. For example, first of all, D
1
—NHR can be condensed with the halotriazine of formula (A) and the resulting reaction product is condensed with 4-amino-2-(2-carboxy ethyl)amino benzene sulfonic acid. The compound (III) is obtained,
wherein X
1
is a fluorine atom or chlorine atom, X, D
1
and R are defined as above.
C) The compound of formula (III) is reacted with a diazonium salt derived from Z
1
—NH
2
to obtain the compounds of formula (IV)
wherein X, D
1
, Z
1
, and R are defined as above. The compounds (IV) can be synthesized by some other methods. For example, the diazonium salt derived from Z
1
—NH
2
is coupled with 4-amino-2-2-carboxyethyl amino benzene sulfonic acid and the resulting reaction product is condensed with a halotriazine of formula (A), followed by reaction with D
1
—NHR to yield a compound of formula (IV).
Another method for the preparation of compounds of formula (IV) is as follows: first, compound D
1
—NHR is condensed with the halotriazine of formula (A). Second, the diazonium salt derived from Z
1
—NH
2
is coupled with 4-amino-2-2-carboxyethyl amino benzene sulfonic acid. Third, the product of the first step is condensed with the product of second step to obtain the compound of formula (IV).
The preparation methods used will be known to those people skilled in the arts. For example, the coupling reaction of diazonium salts onto coupling components is carried out at a pH value between 6 to 8 and temperature between 0 to 25° C. The condensation reaction of an amine is carried out at a pH value between 1 and 10 and temperature between 0 to 80° C.
The reactive dyestuffs of the present invention can be used to amine dye or print hydroxy or amino containing materials such as cotton, wool and nylon, especially cellulose or materials containing cellulose. All natural and regenerated cellulose fibers (e.g. cotton, linen, jute, ramie fiber, viscose rayon) or fiber materials containing cellulose are materials to which the fiber reactive dyestuffs can be applied.
The dyestuffs of the present invention can be used to colour fiber materials by many known methods, for example, exhaust dyeing, continuous dyeing or cold pad batch dyeing.
The dyeing or printing of the dyestuffs of the present invention can be carried out by conventional methods. Exhaust dyeing is carried out by using inorganic salts (e.g. anhydrous sodium sulfate and sodium chloride) and acid-binding agents (e.g. sodium carbonate, sodium hydroxide). Inorganic salts and alkali can be added to the dyebath either in one lot or by portionwise addition. In addition, dyeing assistants can be added. The range of dyeing temperature is from 20° C. to 90° C. Preferably, the temperature for dyeing is from 40° C. to 70° C.
In a cold-pad-batch application, dye, alkali and auxiliaries are padded from the trough liquor. The padded, squeezed substrate is often rolled onto an A-frame and batched at room temperature to allow dye fixation to take place.
Continuous dyeing can be divided into two different methods. In the one-bath padding application, dye, alkali (e.g. sodium carbonate or sodium bicarbonate) and customary auxiliaries are padded from the trough liquor, the padded, squeezed substrate is then dried by either baking or steam. In the two bath padding application, the substrate is padded through a dye solution bath, pre-dried, then passed through an alkali (e.g. sodium hydroxide or sodium silicate) bath, then fixed either by baking or steam.
In textile printing, a substrate is treated with a printing paste containing, a well-known acid-binding agent (e.g. sodium bicarbonate), thickener, and completing the dye fixation by dry heat or steam. The dyeing or printing methods employed in the process of the present invention are no

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