Monoazo reactive red dyestuff

Details Monoazo reactive red dyestuff Monoazo reactive red dyestuff

2002-10-17

2004-11-09

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S638000, C534S642000, C008S549000

Reexamination Certificate

active

06815536

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The invention relates to the technical field of the fiber-reactive dyes, in particular relates to a novel monoazo reactive red dyestuff.
2. Description of Related Art
The practice of dyeing with fiber-reactive dyes has led to heightened expectations of the quality of the dyeings. Consequently there continues to be a demand for novel fiber-reactive dyes that have improved properties. Especially in demand are red reactive dyes having high fastness properties. It is true that British Patent No. 836,248, U.S. Pat. No. 2,979,498 and European Patent Application Publication No. 0 070 806 disclose numerous red fiber-reactive dyes, but the fastness properties of the dyeings obtainable with these dyes, especially the lightfastness and the perspiration lightfastness, are in need of improvement.
U.S. Pat. No. 5,227,475 discloses fiber-reactive dyestuffs having the following formula:
The practice of dyeing using reactive dyestuffs has improved the quality of the dyeings and the efficiency of the dyeing process. Reactive dyestuffs generally display good dyeing and fastness properties but the light fastness, alone and in presence of perspiration, of red fiber-reactive dyestuffs is generally only modest and in need of improvement.
SUMMARY OF THE INVENTION
The present invention provides novel azo compounds having improved properties in this respect and are azo derivatives which compounds conform to the formula (I),
wherein:
X is —NHCN, —OH, —SCH2COOH, —NHSO2CH3, 3-carboxypyridinium,
halogen; preferably X is —NHCN, 3-carboxypyridinium or halogen, wherein the halogen is preferably fluorine or chlorine;
D is a phenyl or naphthyl group having 0 to 3 substituent groups, said substituent groups are selected from the groups consisting of halogen, C
1-4
alkyl, C
1-4
alkoxyl, nitro, amino, hydroxyl, carboxyl, phosphonic acid and sulfo group; preferably D is phenyl having 0 to 3 substituent groups;
Z is —SO
2
—CH═CH
2
or SO
2
—CH
2
—CH
2
—U; U is —OSO
3
H, Cl, Br, —OPO
3
H
2
, —SSO
3
H or
preferably Z is —SO
2
CH═CH
2
or —SO
2
—CH
2
—CH
2
—OSO
3
H;
R
2
is sulfo, carboxy, halogen or C
1-4
alkoxy; preferably R
2
is sulfo or carboxy;
n is 0 or 1, and preferably n is 1;
when X is a halogen atom, R
1
is limited to a hydrogen atom and R
3
is limited to C
1-4
alkyl or C
1-4
alkyl having at least one substituent; preferably when X is fluorine atom or chlorine atom, R
1
is hydrogen atom and R
3
is C
1-4
alkyl;
when X is —NHCN, —OH, —SCH
2
COOH, —NHSO
2
CH
3
, 3-carboxypyridinium or
R
1
and R
3
independently can be any group selected from hydrogen atom, C
1-4
alkyl, phenyl,
or C
1-4
alkyl having one or more substituent group selected from hydroxyl, carboxyl, sulfo, carbamoyl or methoxy carbonyl; preferably R
1
and R
3
is hydrogen atom or C
1-4
alkyl.
The dyestuffs of the present invention is preferably represented by the following formula (Ia),
wherein:
X is —NHCN, —OH, —SCH
2
COOH, —NHSO
2
CH
3
, 3-carboxypyridinium,
halogen; preferably X is —NHCN, 3-carboxypyridinium fluorine or chlorine;
D is a phenyl or naphthyl having 0 to 3 substituent groups, said substituent groups are selected from the group consisting of halogen, C
1-4
alkyl, C
1-4
alkoxyl, nitro, amino, hydroxyl, carboxyl, phosphonic acid and sulfo group;
preferably D is phenyl having 0 to 3 substituent groups;
Z is —SO
2
—CH═CH
2
or SO
2
—CH
2
—CH
2
—U; U is —OSO
3
H, Cl, Br, —OPO
3
H
2
, —SSO
3
H or
preferably Z is —SO
2
CH═CH
2
or —SO
2
—CH
2
—CH
2
—OSO
3
H;
n is 0 or 1, and preferably n is 1;
when X is a halogen atom, R1 is limited to a hydrogen atom and R
3
is limited to C
1-4
alkyl or C
1-4
alkyl having at least one substituent; preferably when X is fluorine atom or chlorine atom, R
1
is hydrogen atom and R
3
is C
1-4
alkyl;
when X is —NHCN, —OH, —SCH
2
COOH, —NHSO
2
CH
3
, 3-carboxypyridinium or
R
1
and R
3
independently can be any group selected from hydrogen atom, C
1-4
alkyl, phenyl,
or C
1-4
alkyl having one or more substituent group selected from hydroxyl, carboxyl, sulfo, carbamoyl or methoxy carbonyl; preferably R
1
and R
3
is hydrogen atom or C
1-4
alkyl.
The formula (I) dyestuff of the present invention is also preferably represented by the following formula (Ib),
wherein:
X is —NHCN, —OH, —SCH
2
COOH, —NHSO
2
CH
3
, 3-carboxypyridinium,
halogen; preferably X is —NHCN, 3-carboxypyridinium, chlorine or fluorine;
Z is —SO
2
—CH═CH
2
or SO
2
—CH
2
—CH
2
—U ; U is —OSO
3
H, Cl or Br; preferably Z is —SO
2
—CH
2
—CH
2
—OSO
3
H;
n is 0 or 1, and preferably n is 1;
when X is a chlorine atom or fluorine atom, R
1
is limited to a hydrogen atom and R
3
is limited to C
1-4
alkyl; preferably R
1
is hydrogen atom and R
3
is methyl or ethyl;
when X is —NHCN, —OH, —SCH
2
COOH, —NHSO
2
CH
3
, 3-carboxypyridinium or
R
1
and R
3
independently can be any group selected from hydrogen atom, C
1-4
alkyl, or C
1-4
alkyl having one or more substituent group selected from hydroxyl, carboxyl, sulfo, carbamoyl or methoxy carbonyl;
preferably when X is fluorine atom or chlorine atom, R
1
and R
3
is hydrogen atom, methyl, or ethyl.
The formula (Ib) dyestuff is preferably the following formula (I-1) dyestuff:
The formula (Ib) dyestuff is preferably the following formula (I-2) dyestuff:
The formula (Ib) dyestuff is preferably the following formula (I-3) dyestuff:
The formula (Ib) dyestuff is preferably the following formula (I-4) dyestuff:
The formula (Ib) dyestuff is preferably the following formula (I-1) dyestuff:
The formula (Ib) dyestuff is preferably the following formula (I-6) dyestuff
These kinds of dyestuffs are suitable for dyeing of materials containing either cellulose fibers, such as cotton, synthetic cotton, hemp, and synthetic hemp, or synthetic polyamide and polyurethane fibers, such as wool, silk, and nylon. Dyed materials with excellent properties can be obtained, showing especially outstanding performance in light fastness.
Other objects, advantages, and novel features of the invention will become more apparent from the following detailed description when taken in conjunction with the accompanying drawings.


REFERENCES:
patent: 4837310 (1989-06-01), Morimitsu et al.
patent: 6114511 (2000-09-01), Dannheim
patent: 62-164765 (1987-07-01), None
patent: 62-167363 (1987-07-01), None
patent: 62-167364 (1987-07-01), None
English abstract of JP 62-164765.*
English abstract of JP 62-167363.*
English abstract of JP 62-167364.

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