Reactive formazan dyestuffs

Details Reactive formazan dyestuffs Reactive formazan dyestuffs

2001-12-14

2002-06-18

Higel, Floyd D. (Department: 1626)

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

Organic compounds

Azo

C534S652000, C544S181000, C544S194000, C544S204000

Reexamination Certificate

active

06407220

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a fiber-reactive dyestuff, especially relates to a novel reactive formazan dyestuff.
BACKGROUND OF THE INVENTION
United Kingdom Patent Publication 1,194,504 discloses formazan derivatives having the following formula:
The fastness and dyeing properties of the said formazan derivatives are not good.
U.S. Pat. No. 4,607,098 discloses compounds of the following formula which exhibit improved fastness but with poor dyeing properties
and fastness to chlorinated water.
U.S. Pat. No. 5,858,026 discloses formazan derivatives having the following formula:
The above formazan derivatives still display poor dyeing properties.
SUMMARY OF THE INVENTION
The present invention provides novel reactive formazan dyestuffs of the following formula (I):
wherein:
A is phenyl or naphthyl having 1 to 4 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, and wherein at least one substituent group is a sulfo group, said sulfo group is in the position ortho to the N-atom of hydrazone compound; preferably A is phenyl having 1 to 4 substituent groups;
B is a straight or branched C
1-8
alkyl, or a phenyl, naphthyl or heteroaromatic group 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, said heteroaromatic group is selected from the group consisting of: furan, thiophene, pyrrole, imidazole, pyrazole, pyridine, pyrimidine, quinoline, or benzimidazole; preferably B is phenyl having 0 to 3 substituent groups;
G 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 G is phenyl having 0 to 3 substituent groups;
Q is —NHCN, —OH, —SCH
2
COOH or 3-carboxypyridinium;
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;
Me is Cu, Ni or Co metal ion; preferably Me is Cu metal ion;
R is H, C
1-8
alkyl, or C
1-8
alkyl having at least one substituent group, said substituent group is selected from the group consisting of hydroxyl, carboxyl, sulfo, carbamoyl, and methoxy carbonyl; preferably R is H, C
1-4
alkyl;
Z is —SO
2
—Y, —CONH—(CH
2
)
h
—SO
2
—Y, —(O)
p
—(CH
2
)
g
—CONH—(CH
2
)
h
—SO
2
—Y, or —NH—CO—T; Y is —CH═CH
2
, or —CH
2
—CH
2
—U; U is —OSO
3
H, Cl, Br, —OPO
3
H
2
, —SSO
3
H or
 T is &agr;, &bgr;-halopropionyl or &agr;-haloacryloyl; g and h independently are an integer from 1 to 6;
P is the number 0 or 1; preferably Z is —SO
2
—Y or —NH—CO—T, and Y is —CH═CH
2
, or —CH
2
—CH
2
—OSO
3
H, and T is &agr;, &bgr;-halopropionyl or &agr;-haloacryloyl.
The compounds of the general formula (I) according to the present invention can be present in the acid form or in the form of their salts, in particular the alkali and alkaline earth metal salts. They find use, preferably in the form of the alkali metal salts, for dyeing and printing hydroxy and/or amide containing materials, in particular fiber materials.
The formula (I) dyestuff of the present invention is preferably the following formula (Ia) dyestuff,
wherein
B is a straight or branched C
1-8
alkyl, or a phenyl, naphthyl or heteroaromatic group 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, said heteroaromatic group is selected from the group consisting of: furan, thiophene, pyrrole, imidazole, pyrazole, pyridine, pyrimidine, quinoline, or benzimidazole; preferably B is phenyl having 0 to 3 substituent groups;
Q is —NHCN, —OH, —SCH
2
COOH or 3-carboxypyridinium;
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;
R is H, C
1-8
alkyl, or C
1-8
alkyl having at least one substituent group, said substituent group is selected from the group consisting of hydroxyl, carboxyl, sulfo, carbamoyl, and methoxy carbonyl; preferably R is H or C
1-4
alkyl;
Z is —SO
2
—Y, —CONH—(CH
2
)
h
—SO
2
—Y, —(O)
p
—(CH
2
)
g
—CONH—(CH
2
)
h
—SO
2
—Y, or —NH—CO—T; Y is —CH═CH
2
, or —CH
2
—CH
2
—U; U is —OSO
3
H, Cl, Br, —OPO
3
H
2
, —SSO
3
H or
 T is &agr;, &bgr;-halopropionyl or &agr;-haloacryloyl; g and h independently are an integer from 1 to 6; P is the number 0 or 1; preferably Z is —SO
2
—Y or —NH—CO—T, Y is —CH═CH
2
, or —CH
2
—CH
2
—OSO
3
H, T is &agr;, &bgr;-halopropionyl or &agr;-haloacryloyl.
The formula (I) dyestuff of the present invention is also preferably the following formula (Ib) dyestuff,
wherein
Q is —NHCN, —OH, —SCH
2
COOH or 3-carboxypyridinium;
R is H, C
1-4
alkyl; preferably R is H;
Z is —SO
2
—Y; Y is —CH═CH
2
or —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.
The formula (I) dyestuff of the present invention is also preferably the following formula (Ic), (Id) or (Ie) dyestuff,
wherein Q, R, D, and Z are define as the formula (Ia) dyestuff of the above.
wherein Q, R, D, and Z are defined as the formula (Ia) dyestuff of the above.
wherein Q, R, D, and Z are defined as the formula (Ia) dyestuff of the above.
The present invention is also related to the process for dyeing and printing cellulosic fiber materials (for example, cotton), which comprises treating the fiber materials with the formula (I) dyestuff in aqueous solution.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The formula (I) dyestuffs of the present invention can be synthesized by the following reaction step (a) to step (c).
Step (a):
The compound of the formula (III) is reacted with 1,3,5-trihalogen triazine of the following formula (IV) to obtain the following formula (V) compound,
wherein Hal is —F, —Cl, —Br; A, B, G, and Me are defined as the formula (I) dyestuff of the above. The reaction is carried out in aqueous solution at a temperature between 0 to 30° C., and below 20° C. is preferred. The acid generated in the reaction is neutralized by adding an acid-binding agent, and the pH is controlled between 1 to 4. Upon completion the reaction, the product of the above formula (V) can be obtained.
Step (b):
The compound of the formula (V) is reacted with the following formula (VI) compound to obtain the following formula (VII) compound,
wherein Hal is —F, —Cl, —Br; A, B, G. and Me are defined as the formula (I) dyestuff of the above. The reaction temperature is controlled between 20 to 80+ C., and 40 to 60° C. is preferred. The acid generated in the reaction is neutralized by adding an acid binding agent. The pH is controlled between 4 to 12, and 7 to 10 is preferred. Upon completion the product of formula (VII) is obtained
Step (c):
After the above reaction is completed, the compound of the following formula (VIII)
wherein R, D, and Z are defined as the above, is then added to the solution of the compound of formula (VII). The reaction temperature is controlled between 30 to 80° C., and 40 to 60° C. is preferred. The acid generated in the reaction is neutralized by adding an acid binding agent. The pH is controlled between 2 to 6, and 3 to 5 is preferred. Upon completion of the reaction, formazan derivatives represented by the above formula (I) dyestuff can be obtained.
In the above reaction steps (a) to (c), the formula (III) and (IV) and (VI) and (VIII) compounds each approximately one molar equivalent, can be reacted with one another in any sequence to yield

Affiliated with

Also associated with

Rating

Reactive formazan dyestuffs 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 formazan dyestuffs, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Reactive formazan dyestuffs will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2898959