U.S. patent application number 12/149301 was filed with the patent office on 2008-08-28 for reactive dyes containing an alkylthio-s-triazinyl reactive group.
This patent application is currently assigned to Everlight USA, Inc.. Invention is credited to Wen-Jang Chen, Duncan Adrian Sidney Phillips, Hsien-Chung Shia, John Anthony Taylor.
Application Number | 20080207881 12/149301 |
Document ID | / |
Family ID | 38786879 |
Filed Date | 2008-08-28 |
United States Patent
Application |
20080207881 |
Kind Code |
A1 |
Chen; Wen-Jang ; et
al. |
August 28, 2008 |
Reactive dyes containing an alkylthio-s-triazinyl reactive
group
Abstract
A reactive dyestuff containing an alkylthio-s-triazinyl reactive
group of the following formula (I) is disclosed, ##STR00001##
wherein A, X, Y, Z, R, Q, and a are defined the same as the
specification. It is suitable for exhaust dyeing, cold batch-up
dyeing and continuous dyeing materials that contain hydroxyl group
or nitrogen group fibers.
Inventors: |
Chen; Wen-Jang; (Taoyuan
Hsien, TW) ; Shia; Hsien-Chung; (Taoyuan Hsien,
TW) ; Phillips; Duncan Adrian Sidney; (Manchester,
GB) ; Taylor; John Anthony; (Manchester, GB) |
Correspondence
Address: |
BACON & THOMAS, PLLC
625 SLATERS LANE, FOURTH FLOOR
ALEXANDRIA
VA
22314
US
|
Assignee: |
Everlight USA, Inc.
Pineville
NC
|
Family ID: |
38786879 |
Appl. No.: |
12/149301 |
Filed: |
April 30, 2008 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
11706363 |
Feb 15, 2007 |
|
|
|
12149301 |
|
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|
Current U.S.
Class: |
534/625 ;
534/622; 534/632; 534/634; 534/636; 534/637; 534/638 |
Current CPC
Class: |
C09B 62/4413 20130101;
D06P 1/38 20130101; C09B 62/4415 20130101; D06P 1/382 20130101;
C09B 62/046 20130101; C09B 62/4416 20130101; C09B 62/10 20130101;
D06P 3/663 20130101; C09B 62/085 20130101; C09B 62/09 20130101;
D06P 3/66 20130101 |
Class at
Publication: |
534/625 ;
534/632; 534/637; 534/636; 534/638; 534/634; 534/622 |
International
Class: |
C07D 251/40 20060101
C07D251/40; C07D 403/12 20060101 C07D403/12; C07F 1/08 20060101
C07F001/08 |
Foreign Application Data
Date |
Code |
Application Number |
Aug 9, 2006 |
CN |
200610112104.7 |
Claims
1. A reactive dyestuff containing an alkylthio-s-triazinyl reactive
group of the following formula (I), ##STR00058## wherein X, Y and Z
are each independently selected from the group consisting of
hydrogen, chlorine, hydroxyl, amino, substituted amino, sulfonate,
arylazo, ##STR00059## alkyl, alkoxy, .alpha.,.beta.-halopropionyl,
.alpha.-haloacryloyl, --B--SO.sub.2CH.sub.2CH.sub.2W,
--B--SO.sub.2CH.dbd.CH.sub.2, --SO.sub.2CH.sub.2CH.sub.2W and
--SO.sub.2CH.dbd.CH.sub.2; B is --CONH--(CH.sub.2).sub.i-- or
--O--(CH.sub.2).sub.j--CONH--(CH.sub.2).sub.k--, wherein i, j and k
are integers independent of one other between 2 to 4; W is selected
from the group consisting of Cl, --OSO.sub.3H, ##STR00060## and
##STR00061## wherein R.sub.9, R.sub.10 and R.sub.11 are each
independently C.sub.1-4 alkyl; Q is C.sub.1-4 alkyl or substituted
C.sub.1-4 alkyl; A is one or more chromophore groups substituted by
one or more sulfo, and selected from the group consisting of
formazan, anthraquinone, phthalocyanine, triphendioxazine, monoazo,
disazo, polyazo and metal complex azo; said disazo and said polyazo
are selected from the group consisting of: ##STR00062## wherein,
R.sub.8 is C.sub.1-4alkyl, C.sub.1-4alkoxyl, carboxyl, sulfo,
acetyl, acetyl amino, ureido, --SO.sub.2CH.sub.2CH.sub.2W or
--SO.sub.2CH.dbd.CH.sub.2; W is defined as above; p is 1 or 2;
R.sub.2 is C.sub.1-4 alkyl, C.sub.1-4 alkoxyl, amino, acetylamino,
ureido or sulfo; q, r, s, t and u are each independently 0, 1, 2 or
3; and m and o are each independently 0, 1, 2 or 3; a is 1 or 2;
and, R is hydrogen, C.sub.1-4 alkyl, or C.sub.1-4 alkyl substituted
by hydroxyl, C.sub.1-4 alkoxy or carboxyl.
2. The reactive dyestuff of claim 1, wherein Q is methyl or ethyl,
which is unsubstituted or substituted by one to three substitutent
groups, and said substitutent groups of the methyl or ethyl group
are independently selected from the group consisting of halogen,
hydroxyl, sulfo, cyano, amino, carbonamido, carboxyl,
alkoxycarbonyl, acyloxy and alkoxy.
3. The reactive dyestuff of claim 1, wherein said chromophore group
A is selected from the group consisting of formazan, anthraquinone,
phthalocyanine, triphendioxazine, monoazo, disazo, polyazo and
metal complex azo.
4. The reactive dyestuff of claim 3, wherein said phthalocyanine is
##STR00063## wherein Pc is copper phthalocyanine or nickel
phthalocyanine; U is --OH and/or --NH.sub.2; E is phenylene or
ethylene; and c+d.ltoreq.4.
5. The reactive dyestuff of claim 3, wherein said triphendioxazine
is selected from the group consisting of ##STR00064## wherein E is
phenylene or ethylene.
6. The reactive dyestuff of claim 3, wherein said monoazo is
selected from the group consisting of: ##STR00065## wherein R.sub.1
is halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxyl, carboxyl, sulfo,
--SO.sub.2CH.sub.2CH.sub.2W or --SO.sub.2CH.dbd.CH.sub.2, and W is
defined the same as in claim 1; R.sub.2 is C.sub.1-4 alkyl,
C.sub.1-4 alkoxyl, amino, acetylamino, ureido or sulfo; R.sub.4 is
C.sub.1-4 alkyl or carboxyl; and m, o and p are each independently
0, 1, 2 or 3.
7. The reactive dyestuff of claim 3, wherein said disazo and said
polyazo are selected from the group consisting of: ##STR00066##
wherein R.sub.8 is C.sub.1-4 alkyl, C.sub.1-4 alkoxyl, carboxyl,
sulfo, acetyl, acetyl amino, ureido, --SO.sub.2CH.sub.2CH.sub.2W or
--SO.sub.2CH.dbd.CH.sub.2, and W is defined the same as in claim 1;
q, r, s, t and u are each independently 0, 1, 2 or 3; R.sub.2, m, o
and p are defined the same as in claim 6.
8. The reactive dyestuff of claim 3, wherein said metal complex azo
is selected from the group consisting of: ##STR00067## wherein m
and o are defined the same as in claim 6.
9. The reactive dyestuff of claim 1, wherein said formula (I) is
the following formula (37). ##STR00068##
Description
[0001] This application is a continuation application of pending
U.S. patent application Ser. No. 11/706,363 filed Feb. 15, 2007 (of
which the entire disclosure of the pending, prior application is
hereby incorporated by reference).
BACKGROUND OF THE INVENTION
[0002] 1. Field of the Invention
[0003] The present invention relates to a novel reactive dyestuff,
and more particularly relates to a reactive dyestuff with
alkylthio-s-triazine.
[0004] 2. Description of the Related Art
[0005] During the period between the 1960's and early 1980's, the
art of a reactive dyestuff with mono alkylthio-s-triazinyl reactive
group was developed. The development was mainly focused on the art
of a reactive dyestuff used thio/sulphur chemistry, which contains
s-triazine or pyramine, as disclosed in British Patent No. GB
923068.
[0006] During 1986-1996, the research of a reactive dyestuff was
continuously developed but limited to a certain scope of
chromophore groups, as disclosed in European Patent No. EP 0264878
and Japanese Patent No. JP 10-001618. A reactive dyestuff taking
monochloro triazine and vinylsulfone as the bifunctional reactive
group is the mainstream in the present market of 60.degree. C. warm
dyeing. However, the activity of the two reactive groups is so
different that it mainly uses vinylsulfonyl reactive group to fix
the dyes on the cellulose fibers in the application of dyeing. On
the contrary, the use of monochloro triazinyl reactive group is
relatively low, since the monochloro triazine is a reactive group
for 80.degree. C. application. While replacing the monochloro
triazine with monofluoro triazine, the activity thereof may be
nearly equal to that of the vinylsulfonyl reactive group and the
tinctorial yield of the dyestuff may be improved. However, the cost
of trifluoro triazine is too high so that the economic benefits of
the dyestuffs become low. The present invention provides an
alkylthio group as a substituent for monochloro triazine, which
makes the activity of the reactive group equal to that of the
vinylsulfonyl reactive group and improves efficiently the
utilization of the reactive group. Thereby, the dyestuff of the
present invention presents properties of high fixation and
excellent build up, and has greater economic benefits than that of
the dyestuff containing monofluoro triazine. The novel reactive
dyestuff of the present invention has improved properties, such as
better reactivity, fixing capacity, build up, stable binding
between fibers and dyestuffs, excellent wash fastness, light
fastness and wet fastness.
[0007] In other words, the present invention provides a novel
dyestuff with bifunctional reactive groups, comprising an alkylthio
group substituent to improve the activity of monochloro triazine,
which has higher reactive selectivity and economic benefits.
SUMMARY OF THE INVENTION
[0008] The present invention provides a reactive dyestuff
containing an alkylthio-s-triazinyl reactive group of the following
formula (I),
##STR00002##
wherein X, Y and Z are each independently selected from the group
consisting of hydrogen, chlorine, hydroxyl, amino, substituted
amino, sulfonate, arylazo,
##STR00003##
alkyl, alkoxy, .alpha.,.beta.-halopropionyl, .alpha.-haloacryloyl,
--B--SO.sub.2CH.sub.2CH.sub.2W, --B--SO.sub.2CH.dbd.CH.sub.2,
--SO.sub.2CH.sub.2CH.sub.2W and --SO.sub.2CH.dbd.CH.sub.2; B is
--CONH--(CH.sub.2).sub.i-- or --O--(CH.sub.2).sub.j--CONH--
(CH.sub.2).sub.k--, wherein i, j and k are integers independent of
one another between 2 to 4; W is selected from the group consisting
of Cl, --OSO.sub.3H,
##STR00004##
and
##STR00005##
wherein R.sub.9, R.sub.10 and R.sub.11 are each independently
C.sub.1-4 alkyl; Q is C.sub.1-4 alkyl or substituted C.sub.1-4
alkyl; A is one or more chromophore groups substituted by one or
more sulfo; a is 1 or 2; R is hydrogen, C.sub.1-4 alkyl, or
C.sub.1-4 alkyl substituted by hydroxyl, C.sub.1-4 alkoxy or
carboxyl.
[0009] The reactive dyestuff of formula (I) of the present
invention contains one or more chromophore groups, which can
connect with one or more sulfo and at least two fiber-reactive
groups, wherein one of the fiber-reactive groups must be
##STR00006##
[0010] In the reactive dyestuff of formula (I) of the present
invention, Q is preferable a methyl or ethyl group, which is
unsubstituted or substituted by one to three substitutent groups.
The substitutent groups of the methyl or ethyl group are
independently selected from the group consisting of halogen,
hydroxyl, sulfo, cyano, amino, carbonamido, carboxyl,
alkoxycarbonyl, acyloxy and alkoxy.
[0011] In the reactive dyestuff of formula (I) of the present
invention, the chromophore group A is preferably selected from the
group consisting of formazan, anthraquinone, phthalocyanine,
triphendioxazine, monoazo, disazo, polyazo and metal complex
azo.
[0012] Preferably, the structure of phthalocyanine chromophore
group is as the following formula:
##STR00007##
wherein Pc is copper phthalocyanine or nickel phthalocyanine; U is
--OH and/or --NH.sub.2; E is phenylene or ethylene; and
c+d.ltoreq.4.
[0013] The triphendioxazine chromophore group is preferably
selected from the group consisting of:
##STR00008##
wherein E is phenylene or ethylene.
[0014] The monoazo chromophore group is preferably selected from
the group consisting of:
##STR00009##
wherein R.sub.1 is halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxyl,
carboxyl, sulfo, --SO.sub.2CH.sub.2CH.sub.2W or
--SO.sub.2CH.dbd.CH.sub.2, and W is defined the same as the
aforementioned; R.sub.2 is C.sub.1-4 alkyl, C.sub.1-4 alkoxyl,
amino, acetylamino, ureido or sulfo; R.sub.4 is C.sub.1-4 alkyl or
carboxyl; and m, o and p are each independently 0, 1, 2 or 3.
[0015] The disazo and polyazo chromophore groups are preferably
selected from the group consisting of:
##STR00010##
wherein R.sub.8 is C.sub.1-4 alkyl, C.sub.1-4 alkoxyl, carboxyl,
sulfo, acetyl, acetyl amino, ureido, --SO.sub.2CH.sub.2CH.sub.2W or
--SO.sub.2CH.dbd.CH.sub.2 and W is defined the same as the
aforementioned; q, r, s, t and u are each independently 0, 1, 2 or
3; R.sub.2, m, o and p are defined the same as the
aforementioned.
[0016] The metal complex azo chromophore group is preferably
selected from the group consisting of:
##STR00011##
wherein m and o are defined the same as the aforementioned.
[0017] For describing conveniently, the compound is expressed as
free acid in the specification. When produced or used, the reactive
dyestuffs of the present invention are often presented as
water-soluble salts. The salts suitable for the present invention
may be the alkaline metal salts, alkaline earth metal salts,
ammonium salts or organic amine salts; preferably, the salts are
sodium salts, potassium salts, lithium salts, ammonium salts or
triethanolamine salts.
[0018] The dyestuff of the present invention can be applied to dye
and print on many kinds of fiber materials, particularly cellulose
fiber materials and cellulose-included fiber materials. The
examples of the fiber materials are not limited. It can be natural
or regenerated cellulose fibers, such as cotton, hemp, linen, jute,
ramie, mucilage rayon, as well as cellulose-included fiber
materials. The dyestuff of the present invention can also be
applied to dye and print fiber blended fabrics containing hydroxyl
groups.
[0019] The dyestuff of the present invention can be applied to the
fiber material and fixed on the fiber in various ways, in
particularly in the form of aqueous dyestuff solutions and printing
pastes. They can be applied to cellulose fibers by general dyeing
methods, such as exhaustion dyeing, continuous dyeing,
cold-pad-batch dyeing, printing or digital printing.
[0020] The dyeing or printing of the present invention can be
proceeded by the conventional and usually known method. For
example, exhaustion dyeing is applied by using separately or mixing
the well-known inorganic salts (e.g. sodium sulfate and sodium
chloride) and acid-binding agents (e.g. sodium carbonate, sodium
hydroxide). The amount of inorganic salts and alkali does not
matter. The inorganic salts and alkali can be added either once or
several times into the dyeing bath through traditional methods. In
addition, dyeing assistant agents (such as leveling agent,
suspending agent and so on) can be added according to conventional
method. The range of dyeing temperature is from 40.degree. C. to
90.degree. C. Preferably, the temperature for dyeing is from
40.degree. C. to 70.degree. C.
[0021] In the cold-pad-batch dyeing method, the material is padded
by using the well-known inorganic salts (e.g. sodium sulfate and
sodium chloride) and acid-binding agents (e.g. sodium carbonate,
sodium hydroxide). The padded fabric is rolled and stored at room
temperature to allow dye fixation to take place.
[0022] In the continuous dyeing method, two different methods
exist. In the one-bath pad dyeing method, the material is padded
according to the conventional method in the mixture of the
well-known acid-binding agents (e.g. sodium carbonate or sodium
bicarbonate) and the pad liquid. The resultant material is then
dried and color fixed by baking or steaming. In the two-bath pad
dyeing method, the material is padded with a dye liquid and then
dealt by a known inorganic neutral salt (e.g., sodium sulfate or
sodium silicate). The dealt material is preferably dried and color
fixed by baking or steaming as usual.
[0023] In the textile printing method, such as single printing
method, the material is printed by printing slurry containing the
known acid-binding agent (e.g., sodium bicarbonate) and is dried
and color fixed by baking or steaming. In the two-phase printing
method, the material is dipped in a solution containing inorganic
neutral salt (e.g., sodium chloride) and the known acid-binding
agent (e.g., sodium hydroxide- or sodium carbonate) in a high
temperature of 90.degree. C. or above to fix the color. The dyeing
or printing methods employed in the process of the present
invention are not limited to the above methods.
[0024] The dyestuff of the present invention is a valuable reactive
dyestuff for cellulose fibers in the present dyeing industry. The
dyestuff has properties of excellent fixing capacity, outstanding
build up and high wash-off and is suitable for dyeing in a wide
range of temperatures, which make the dyestuff suitable for dyeing
cotton/polyester blended fabrics as well. The dyestuff of the
present invention is also suitable for printing, particularly when
applying in printing cotton or blended fabrics that contain wool or
silk. In the dyeing or printing of cellulose fiber materials, dyed
products with various fine dyeing properties are obtained;
particularly dyeing, printing or batch-up dyeing products with high
quality can be obtained in respect of build up and wash
fastness.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT
[0025] The dyestuff of the present invention may be prepared by
conventional methods, of which diazotization, coupling and
condensation reaction are usually used in the field and can be
accomplished by one skilled in the art.
[0026] Hereinafter, the present invention will be further
explained. However, it is to be understood that the examples below
are only for illustrated, but not to limit the scope of the present
invention. The compounds are represented in the form of free acid.
However, in practice, they often exist as metallic salts, and most
likely alkaline metallic salts, particularly sodium salts. Unless
otherwise stated, the parts and percentage used in the following
examples are based on weight, and the temperature is in Celsius
degree (.degree. C.).
Example 1
[0027] (a) 19.45 parts of cyanuric chloride is dispersed in 150
parts of 0.degree. C. water, and then 31.9 parts of
2-amino-5-hydroxy-naphthalene-1,7-disulfonic acid powder is added
therein. The pH value of the reaction solution is adjusted to 3 by
15% of Na.sub.2CO.sub.3 aqueous solution. The temperature of the
aqueous solution is raised smoothly to 20.degree. C. and then
maintained for 1.about.2 hours.
[0028] (b) 9.7 parts of thioglycolic acid is added to the solution
obtained from the above (a) step. At 20.degree. C., the pH value of
the reaction solution is adjusted to 7.about.7.5 by 18 parts of
Na.sub.2CO.sub.3 powder and maintained for 15 minutes, followed by
adjusting the pH value of the reaction solution to 6.about.6.5 by
HCl aqueous solution. The filter cake is obtained by well-known
NaCl salting-out and filtration.
[0029] (c) 29.5 parts of
2-methoxy-4-(.beta.-sulfatoethylsulfonyl)aniline and 30 parts of
32% HCl aqueous solution are added to 150 parts of 0.degree. C.
water and then the solution is stirred thoroughly, followed by the
rapid addition of 7.2 parts of sodium nitrite aqueous solution.
Diazotization is carried out for 1.5 hours at 0.about.5.degree. C.,
followed by the addition of the filter cake obtained from the above
(b) step. The pH value is adjusted slowly to 6.about.6.5 by sodium
bicarbonate. After completion of the reaction, the orange product
of the following formula (I) is obtained by salting-out, filtration
and dryness.
##STR00012##
Example 2
[0030] (a) 19.45 parts of cyanuric chloride is dispersed in 150
parts of 0.degree. C. water, and then 31.5 parts of
1-naphthol-8-amino-3,6-disulfonic acid powder is added therein. The
pH value of the reaction solution is adjusted to 3 by 15% of
Na.sub.2CO.sub.3 aqueous solution. The temperature of the aqueous
solution is raised smoothly to 20.degree. C. and then maintained
for 1.about.2 hours.
[0031] (b) 9.7 parts of thioglycolic acid is added to the solution
obtained from the above (a) step. At 20.degree. C., the pH value of
the reaction solution is adjusted to 7.about.7.5 by 18 parts of
Na.sub.2CO.sub.3 powder and maintained for 15 minutes, followed by
adjusting the pH value of the reaction solution to 6.about.6.5 by
HCl aqueous solution. The filter cake is obtained by well-known
NaCl salting-out and filtration.
[0032] (c) 29 parts of 4-(.beta.-sulfatoethylsulfonyl) aniline and
50 parts of 32% HCl aqueous solution are added to 150 parts of
0.degree. C. water and then the solution is stirred thoroughly,
followed by the rapid addition of 7.2 parts of sodium nitrite
aqueous solution. Diazotization is carried out for 1.5 hours at
0.about.5.degree. C., followed by the addition of the filter cake
obtained from the above (b) step. The pH value is adjusted slowly
to 6.about.6.5 by sodium bicarbonate. After completion of the
reaction, the red product of the following formula (2) is obtained
by salting-out, filtration and dryness.
##STR00013##
Example 3
[0033] (a) 19.45 parts of cyanuric chloride is dispersed in 150
parts of 0.degree. C. water, and then 18.8 parts of
1,3-phenylenediamine-4-sulfonic acid powder is added therein. The
pH value of the reaction solution is adjusted to 3 by 15% of
Na.sub.2CO.sub.3 aqueous solution. The temperature of the aqueous
solution is raised smoothly to 20.degree. C. and then maintained
for 1.about.2 hours.
[0034] (b) 9.7 parts of thioglycolic acid is added to the solution
obtained from the above (a) step. At 20.degree. C., the pH value of
the reaction solution is adjusted to 7.about.7.5 by 18 parts of
Na.sub.2CO.sub.3 powder and maintained for 15 minutes, followed by
adjusting the pH value of the reaction solution to 6.about.6.5 by
HCl aqueous solution. The filter cake is obtained by well-known
NaCl salting-out and filtration.
[0035] (c) 19.5 parts of the filter cake obtained from the above
(b) step and 25 parts of 32% HCl aqueous solution are added to 150
parts of 0.degree. C. water and then the solution is stirred
thoroughly, followed by the rapid addition of 3.6 parts of sodium
nitrite aqueous solution. Diazotization is carried out for 1.5
hours at 0.about.5.degree. C., followed by the addition of 16.0
parts of 1-naphthol-8-amino-3,6-disulfonic acid powder. The pH
value is adjusted slowly to 3 by 10 parts of sodium bicarbonate.
After completion of the reaction, the filter cake is obtained by
salting-out and filtration.
[0036] (d) 16.55 parts of
1-aminobenzene-4-(.beta.-sulfatoethylsulfonyl)-2-sulfonic acid and
12.6 parts of 32% HCl aqueous solution are added to 150 parts of
0.degree. C. water and then stirred thoroughly, followed by the
rapid addition of 3.7 parts of sodium nitrite aqueous solution.
Diazotization is carried out for 1.about.2 hours at
0.about.5.degree. C. and then the filter cake obtained from the
above (c) step is added into the diazonium salt solution. The pH
value is adjusted slowly to 5.about.6 by sodium carbonate. After
completion of the reaction, the navy product of the following
formula (3) is obtained by salting-out, filtration and dryness.
##STR00014##
[0037] According to the synthetic methods of Example 1.about.3, the
dyestuffs of the following examples 4.about.36 are obtained. In the
table, the color appearance is the color of the dyestuff dissolved
in water.
TABLE-US-00001 color Exam- appear- ple Structure of dyestuff ance 4
##STR00015## BrilliantYellow 5 ##STR00016## Yellow 6 ##STR00017##
Yellow 7 ##STR00018## Yellow 8 ##STR00019## Yellow 9 ##STR00020##
Yellow 10 ##STR00021## Yellow 11 ##STR00022## Yellow 12
##STR00023## Orange 13 ##STR00024## Orange 14 ##STR00025## Orange
15 ##STR00026## Orange 16 ##STR00027## Orange 17 ##STR00028##
DullOrange 18 ##STR00029## Red 19 ##STR00030## Red 20 ##STR00031##
Red 21 ##STR00032## Red 22 ##STR00033## Red 23 ##STR00034## Red 24
##STR00035## Red 25 ##STR00036## Red 26 ##STR00037## Red 27
##STR00038## Brown 28 ##STR00039## Scarlet 29 ##STR00040## Rubin 30
##STR00041## Violet 31 ##STR00042## Navy 32 ##STR00043## Navy 33
##STR00044## Navy 34 ##STR00045## Navy 35 ##STR00046## Navy 36
##STR00047## Green
Example 37
[0038] (a) 19.45 parts of cyanuric chloride is dispersed in 150
parts of 0.degree. C. water, and then 18.8 parts of
1,3-phenylenediamine-4-sulfonic acid powder is added therein. The
pH value of the reaction solution is adjusted to 3 by 15% of
Na.sub.2CO.sub.3 aqueous solution. The temperature of the aqueous
solution is raised smoothly to 20.degree. C. and then maintained
for 1.about.2 hours for the next step.
[0039] (b) 9.7 parts of thioglycolic acid is added to the solution
obtained from the above (a) step. At 20.degree. C., the pH value of
the reaction solution is adjusted to 7.about.7.5 by 18 parts of
Na.sub.2CO.sub.3 powder and maintained for 15 minutes, followed by
adjusting the pH value of the reaction solution to 6.about.6.5 by
HCl aqueous solution. The filter cake is obtained by well-known
NaCl salting-out and filtration.
[0040] (c) 19.5 parts of the filter cake obtained from the above
(b) step and 25 parts of 32% HCl aqueous solution are added to 150
parts of 0.degree. C. water and then the solution is stirred
thoroughly, followed by the rapid-addition of 3.6 parts of sodium
nitrite aqueous solution. Diazotization is carried out for 1.5
hours at 0.about.5.degree. C., followed by the addition of 8.0
parts of 1-naphthol-8-amino-3,6-disulfonic acid powder. The pH
value is adjusted slowly to 3 by 10 parts of sodium bicarbonate to
accomplish the coupling reaction. After completion of the reaction,
the dark blue product of the following formula (37) is obtained by
salting-out, filtration and dryness.
##STR00048##
Examples 38.about.46
[0041] According to the synthetic method of Example 37, the
dyestuffs of the following examples 38.about.46 are obtained. In
the table, the color appearance is the color of the dyestuff
dissolved in water.
TABLE-US-00002 Color Exam- appear- ple Structure of dyestuff ance
38 ##STR00049## Orange 39 ##STR00050## Red 40 ##STR00051## Red 41
##STR00052## Red 42 ##STR00053## Scarlet 43 ##STR00054## Navy 44
##STR00055## Green 45 ##STR00056## Blue 46 ##STR00057##
Tur-quoise
Testing Example 1
[0042] 0.25 parts of the dyestuff as prepared in example 1 is
dissolved in 250 mL of water to obtain a dye liquid. To 40 mL of
the dye liquid, in a dyeing bottle, 2 parts of cotton fabric is
added, followed by addition of 2.4 parts of Glauber's salt, and
finally 2.5 mL of 32% alkali solution. The dyeing bottle is placed
in a horizontal shaking bath at 60.degree. C. while maintaining the
temperature for 60 minutes. The obtained golden fabric is orderly
washed with cold water, boiling water for 10 minutes, boiling
non-ionic detergent for 10 minutes, and again with cold water and
then dried to obtain an orange dyeing product with good build up
and tinctorial yield.
Testing Example 2
[0043] 100 parts of Urea, 10 parts of m-nitrobenzene sulfonic acid
sodium salt, 20 parts of sodium bicarbonate, 55 parts of sodium
alginate, and 815 parts of lukewarm water are stirred in a vessel
to obtain a completely homogeneous printing paste.
[0044] 3 parts of the dyestuff prepared in example 2 is sprayed in
100 parts of the above printing paste and stirred to make a
homogeneous colored paste. An adequate size piece of twilled cotton
fabric is covered with a 100 mesh 45.degree.-twilled printing
screen and then painted with the colored paste on the printing
screen to give a colored fabric.
[0045] This colored fabric is placed in an oven at 65.degree. C.
for 5 minutes until dry and then put into a steaming oven using
saturated steam of 102.about.105.degree. C. for 10 minutes.
[0046] The obtained rosy fabric is orderly washed with cold water,
boiling water for 10 minutes, boiling non-ionic detergent for 10
minutes, again with cold water and then dried to obtain a red
fabric with good build up and good tinctorial yield.
Testing Example 3
[0047] 3 parts of the dyestuff prepared in example 3 is dissolved
in 100 mL of water to obtain a 30 parts/l padding liquor. 25 ml of
alkali solvent (taking 15 ml/l of NaOH (38.degree. Be') and 30
parts/l of Glauber's salt) is added to the padding liquor and
stirred thoroughly. The resultant solution is then put into a pad
roller machine. The cotton fabric is padded by the roller pad
machine, and batched for 4 hours under room temperature. The
obtained orange fabric is orderly washed with cold water, boiling
water for 10 minutes, boiling non-ionic detergent for 10 minutes,
again with cold water and then dried to obtain a navy fabric with
good build up and good tinctorial yield.
[0048] From the foregoing description, the technology according to
the present invention achieves the objects of the invention and
conforms to the patent requirements of novelty, inventive step and
industrial applicability. Although the present invention has been
explained in relation to its preferred examples, it is to be
understood that many other possible modifications and variations
can be made without departing from the scope of the invention as
hereinafter claimed.
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