CN102585553B - Navy-blue reactive dye composition and dyeing application thereof - Google Patents
Navy-blue reactive dye composition and dyeing application thereof Download PDFInfo
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- CN102585553B CN102585553B CN2011100071997A CN201110007199A CN102585553B CN 102585553 B CN102585553 B CN 102585553B CN 2011100071997 A CN2011100071997 A CN 2011100071997A CN 201110007199 A CN201110007199 A CN 201110007199A CN 102585553 B CN102585553 B CN 102585553B
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Abstract
The invention provides a navy-blue reactive dye composition and the dyeing application thereof. The dye composition contains one or more dye compounds represented by a general formula (1), one or more dye compounds represented by a general formula (2), and one or more dye compounds represented by a general formula (3). The navy-blue active dye composition has an excellent dyeing property, favorable color fastness of each item, and excellent dyeing compatibility with other commonly-used red and yellow reactive dyes. The general formulas (1, 2 and 3) are figured.
Description
Technical field
The present invention relates to a kind of reactive dye compositions and, in the tint applications of filamentary material, particularly, the present invention relates to a kind of navy blue reactive dye composition and the tint applications on filamentary material thereof.
Background technology
The development research of dark blue reactive dye is one of focus of current dyestuff circle concern always.This is not only blueness consumption maximum in all tones, and it is again the main component of spelling black and active dye composition or mixture.
Along with the performance requriements to printed fabrics is day by day harsh, dark blue reactive dye must possess the dyefastness of every excellence, but also should have good application performance, such as enhancing rate, dye uptake, degree of fixation and consistency etc.
The present invention relates to a kind of navy blue reactive dye composition, by compound synergic, thereby significantly improve its tint applications performance and dyefastness.
One of component of the navy blue reactive dye composition the present invention relates to is a kind of first of copper-containing metal
Class (Formazan) dyestuff.
Nineteen eighty-two Hoechst company delivers structure and the synthetic method thereof that U.S. Pat 4336190 discloses this class dyestuff.The structure of this class dyestuff is meaned by general formula (1):
General formula (1)
In formula: Y
1, R
1, M, p, t implication be referring to following detailed description.
Above-mentioned dyestuff color and luster is turquoise, has good every dyefastness.What particularly speak approvingly of is its very excellent colour fastness to light and the photochromic fastness of sweat proof.
But regrettably, the dyestuff of this class formation exists defect and deficiency at the tint applications aspect of performance.For example enhancing rate is not high, is difficult to dye dark color; Consistency is not good, is difficult to dye together with redness commonly used and yellow dyes; Degree of fixation is also not ideal enough etc.Thereby, as commercial dye, its tint applications performance is anxious to be waited to improve.
Improve one of the measure of the application performance of above-mentioned dyestuff, the dye composite or the mixture that one of are that to form this dyestuff be component.The inventor watches following technical progress attentively:
1) adopt homologue to mix.See US 6143039 (2000) (Dystar).
2) adopt C.I.Reactive Black 5 or derivatives thereofs and its composition mixture or composition.Relevant patent is shown in:
US 5632783(1997)(BASF)
US 5704951(1998)(Hoechst)
US 6171248(2001)(Dystar)
The inventor, on the basis of a large amount of research trials, examines above-mentioned dye composite or mixture closely, finds that these reactive dye compositionss or mixture remain the deficiency at dyeing behavior or fastness ability, are further improved.
The inventor, by test, finds above-mentioned 2 pleasantly surprisedly) in improvement project, add the 3rd component that general formula (3) means, can effectively improve fastness ability.
The data of relevant prompting ternary mixture provided by the present invention or composition, be not seen in the patent report.
Summary of the invention
The inventor, by experimental study, is surprised to find the blue active dye compound that contains one or more general formulas (1) and mean, the black-and-blue reactive dye compound of one or more general formulas (2) expression and the dark blue dye composition of the dark blue reactive dye compound that one or more general formulas (3) mean and has very excellent dyeing behavior and every fastness.
What be worth proposition is, the tint applications performance of navy blue reactive dye composition of the present invention and every dyefastness, take in the length that it forms the characteristic of dyestuff concurrently, make up some defect that it forms dyestuff, particularly improved fastness ability, obvious improvement all occurs in especially fastness to chlorine performance, and its level-dyeing property, consistency.Navy blue reactive dye composition of the present invention, cost of manufacture is cheap, can form three primary colors with conventional red, yellow dye and use.Can predict, navy blue reactive dye composition of the present invention has wide prospects for commercial application.
Navy blue reactive dye composition provided by the invention comprises the dye composition of one or more general formulas (1) expression that certain proportion mixes, the dye composition that one or more general formulas (2) mean, and the dye composition of one or more general formulas (3) expression:
General formula (1)
In formula:
R
1For H ,-Cl, C
1-C
4Alkyl, C
1-C
4Alkoxyl group or-SO
3M;
Y
1For-CH
2CH
2OSO
3M or-CH=CH
2
M is H or alkali metal cation;
P is 0 or 1;
T is 0 or 1.
General formula (2)
In formula:
Y
3And Y
4Be independently-CH respectively
2CH
2OSO
3M or-CH=CH
2
R
2, R
3, R
4And R
5Be H, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or sulfonic group;
M is H or alkali metal cation.
General formula (3)
In formula:
T is-NHCOQ or-SO
2Y
2
Q is-CHXCH
2X or-CX=CH
2
X is Cl or Br;
Y
2For-CH
2CH
2OSO
3M or-CH=CH
2
M is H, Na, K or NH
4 +Group;
R
6And R
7Be H, halogen, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or sulfonic group;
N is 0,1 or 2.
The present invention also provides the application of above-mentioned navy blue reactive dye composition at the dyeing aspect of hydroxyl and/or formamido-material, particularly filamentary material.
Specific implementation method
Dye combinations species of the present invention, comprise dyestuff, the dyestuff of one or more general formulas (2) expression and the dyestuff that one or more general formulas (3) mean that one or more general formulas (1) mean.
In dye composite of the present invention, the weight ratio of the dyestuff that the dyestuff that the dyestuff that general formula (1) means and general formula (2) mean and general formula (3) mean is: 20～60: 20～55: 5～60, be preferably 20～50: 20～50: 10～50.
One preferred embodiment in, in general formula (1) left side-SO
3Contraposition or a position of be positioned on benzene nucleus-COO group of M group; The right side on the middle right side of general formula (1)-SO
2Y
1Ortho position or a position of be positioned on benzene nucleus-N=N-group of group, when t=1, in general formula (1) right side-SO
3Position between be positioned on benzene nucleus-N=N-group of M group.
Another preferred embodiment in, the R of general formula (1) downside
1Group, when p=1, be positioned at being positioned on benzene nucleus on benzene nucleus
Position or contraposition between group.
One preferred embodiment in, the R in general formula (2)
2, R
3, R
4And R
5Ortho position, a position and the contraposition of be separately located in respectively on benzene nucleus-N=N-group of group.
Another preferred embodiment in, in general formula (2)-SO
2Y
3With-SO
2Y
4Ortho position, a position and the contraposition of be separately located in respectively on benzene nucleus-N=N-group of group.
One preferred embodiment in, the T group in general formula (3), contraposition or a position of be positioned on benzene nucleus-N=N-group.
Another preferred embodiment in, the R in general formula (3)
6Group and R
7Ortho position, a position or the contraposition of be separately located in respectively on benzene nucleus-N=N-group of group.
One preferred embodiment in, general formula (3) left side-(SO
3M) n group, the ortho position of when n=1, be positioned on benzene nucleus-N=N-group, a position or contraposition; When n=2, ortho position and contraposition or ortho position and a position of be positioned on benzene nucleus-N=N-group.
Another preferred embodiment in, the NHCOQ group in left side in general formula (3), ortho position, a position or the contraposition of be positioned on benzene nucleus-N=N-group.
The dye composition that general formula (1) means for example comprises following example:
Dyestuff 1-1
Dyestuff 1-2
Dyestuff 1-3
Dyestuff I-4
Dyestuff I-5.
The dye composition that general formula (2) means for example comprises following example:
Dyestuff 2-1
Dyestuff 2-2
Dyestuff 2-3
Dyestuff 2-4
Dyestuff 2-5 or
Dyestuff 2-6.
The dye composition that general formula (3) means for example comprises following example:
Dyestuff 3-1
Dyestuff 3-2
Dyestuff 3-3
Dyestuff 3-4
Dyestuff 3-5
Dyestuff 3-6
Dyestuff 3-7 or
Dyestuff 3-8.
The reactive dye compound that general formula (1), general formula (2) and general formula (3) mean is known dye.
Structure and the synthetic method of the reactive dye compound that general formula (1) means, see following patent:
US 4336190(1982)(Hoechst)
US 4370145(1983)(Hoechst)
US 5028700(1991)(Hoechst)
US 5563248(1996)(Hoechst)
US 6143039(2000)(Dystar)
Structure and the synthetic method of the reactive dye compound that general formula (2) means, see following patent:
JP 5328626(1997)(Hoechst)
US 2003/0229952 (2003) (Joachim Eichhorn (DE)) etc.
Structure and the synthetic method of the reactive dye compound that general formula (3) means, see following patent:
CN 101215427 (2008) (the Tianjin moral is triumphant)
CN 101418133 (2009) (the Tianjin moral is triumphant)
US 6537332(2003)(Ciba Speciality Chemicals Corp)
US 5849887(1998)(Ciba Speciality Chemicals Corp)
The full content of above-mentioned document is referred in the present invention.
Navy blue reactive dye composition of the present invention also can contain the dye additive of various conventional uses in dyeing and dye formulations, and its consumption can be selected according to actual needs, and there is no particular limitation, and one is no more than 20 % by weight.For example, electrolyte salt, as sodium sulfate or Repone K, content 0～10 % by weight, preferably 2～6 % by weight; PH adjusting agent, as SODIUM PHOSPHATE, MONOBASIC or Sodium phosphate dibasic, content 0～5 % by weight, preferred 0.5～2.5 % by weight, dust-proofing agent 0～10 % by weight, preferred 0.1～2 % by weight; Solubility promoter 1～15 % by weight, preferred 0.1～3 % by weight.The present composition also can be basically be comprised of general formula (1) dyestuff of above-mentioned weight ratio and general formula (2) dyestuff and general formula (3) dyestuff.
The preparation method of navy blue reactive dye composition of the present invention comprises above-mentioned general formula (1) dyestuff and general formula (2) dyestuff and general formula (3) dyestuff weight ratio is in accordance with regulations mixed.Mix available various ordinary method, as the mechanically mixing method.During mixing, general formula (1) dyestuff and general formula (2) dyestuff and general formula (3) dyestuff can powder types, or with particle form, or exist with aqueous solution form.For example, mixing step can suitable shredder as ball mill or needle mill in and in kneader or mixing machine, carry out.
Navy blue reactive dye composition of the present invention is suitable for dyeing and various materials widely thereof, particularly contain the material of carboxylic acid and/or formamido-, filamentary material more especially, for example cotton, flax and hemp fibre, and Mierocrystalline cellulose and regenerated cellulose, polyester or polyamide fiber material etc.
Navy blue reactive dye composition of the present invention can be applied to filamentary material and be affixed on fiber by several different methods as known in the art, for example can be dyeed by dip-dye method or pad dyeing method.
Embodiment
Every testing method of embodiment
The properties of the present embodiment is tested by following every testing method
1, enhancing rate test: pure cotton fabric is pressed to 60 ℃ of constant temperature dyeings of reactive dyestuffs, and dyeing concentration is 0.5%, 1%, 2%, 4%, 6%o.w.f (dyestuff is to the fabric weight).After dyeing, fabric, after fixed temperature and humidity is processed, is tested its Apparent Depth K/S value record with the Datacolor color measurement instrument.
2, just dye rate and degree of exhaustion test: the dye liquor preparation, press 60 ℃ of constant temperature dyeings of reactive dyestuffs.Respectively before adding alkali and on dye and finish to sample before soap boiling, measure the absorbance of dyeing residual liquid, with dye liquor absorbance before dyeing relatively.
Just dye rate=(1-adds the absorbance of the absorbance of dye liquor before alkali/front dye liquor of dyeing) * 100%
Degree of exhaustion=the absorbance of dye liquor before the absorbance of front dye liquor/dyeing (1-soap) * 100%
3, move the test of staining index MI value: two onesize A, B cloth specimen are dropped into and be added with in the dye bath of dyestuff, sodium sulfate, after 60 ℃ of dyeing 30min, take out the B cloth specimen, the B cloth specimen is put in the blank dye bath that only contains sodium sulfate, put into onesize calico C simultaneously, continue to add sodium carbonate fixation 60min after dyeing (move and dye) 20min.The color strength (K/S) that compares B cloth specimen and C cloth specimen.
Move color strength (K/S) * 100% of the color strength (K/S) of staining index MI=C cloth specimen/B cloth specimen
4, colour fastness to perspiration test: measure by international standard ISO 105-E04.
5, fastness to soaping test: measure by international standard ISO 105-C10.
6, color fastness to water test: measure by international standard ISO 105-E01.
7, colour fasteness to sunlight test: measure by international standard ISO 105-B02.
8, colour fastness to chlorinated water test: measure by international standard ISO 105E03.
Dye type shown according to the form below 1 and consumption thereof evenly mix various dye components by ordinary method in this area, the various navy blue reactive dye compositions of the preparation embodiment of the present invention.
" % " in table 1 all means % by weight, and the gross weight of dye composite of take is benchmark.
Table 1
| Numbering | The reactive dyestuffs title | Form |
| 1 | A | 45% dyestuff 1-1+45% dyestuff 2-1+10% dyestuff 3-1 |
| 2 | B | 50% dyestuff 1-1+25% dyestuff 2-1+25% dyestuff 3-1 |
| 3 | C | 25% dyestuff 1-1+25% dyestuff 2-1+50% dyestuff 3-1 |
| 4 | D | 45% dyestuff 1-2+45% dyestuff 2-2+10% dyestuff 3-4 |
| 5 | E | 50% dyestuff 1-1+25% dyestuff 2-2+25% dyestuff 3-4 |
| 6 | F | 25% dyestuff 1-1+25% dyestuff 2-2+50% dyestuff 3-4 |
| 7 | Reference X | 50% dyestuff 1-1+50% dyestuff 2-1 |
| 8 | Reference Y | 50% dyestuff 1-1+50% dyestuff 3-1 |
| 9 | Reference U | 100% dyestuff 1-1 |
| 10 | Reference V | 100% dyestuff 2-1 |
| 11 | Reference Z | 100% dyestuff 3-1 |
*Reference X is (BASF) cited embodiment of US 5632783 (1997)
*Reference Y is the cited embodiment of application number 2009102475042 patents
Embodiment 1
The coloured light of navy blue reactive dye composition of the present invention
(the 1 dyestuff color and luster meaned is turquoise and color and luster is more shallow, can not be used as the three primary colors blue color component, and the dyestuff color and luster that general formula (2) and general formula (3) mean is dark navy for general formula.
The coloured light of reactive dye compositions of the present invention can be adjusted the ratio of general formula (1) dyestuff and general formula (2) dyestuff and general formula (3) dyestuff as required, thereby make mixture effectively with other redness, yellow dyes, form the three primary colors combination, improve its actual application value.
Embodiment 2
Enhancing rate test (the K/S value at absorbing wavelength 620nm place)
Be determined as follows as stated above the enhancing rate of dyestuff, test result is recorded in table 2
Table 2
From table 2:
Navy blue reactive dye composition of the present invention, compare with the reference dyestuff, and its enhancing rate increases significantly.
Embodiment 3
Just dying rate and degree of exhaustion measures
Be determined as follows as stated above first rate and the degree of exhaustion of dying of dyestuff, test result is recorded in table 3
Table 3
From table 3:
1) the first rate of dying of navy blue reactive dye composition of the present invention is compared with the reference dyestuff, slightly is improved, and has improved the reference dye affinity too low, easily produces the shortcoming of migration, shows, red yellow with conventional three primary colors good consistency when dying;
2) navy blue reactive dye composition of the present invention is compared degree of exhaustion with the reference dyestuff and is improved.
Embodiment 4
Moving staining index measures
Be determined as follows as stated above the staining index that moves of dyestuff, test result is recorded in table 4
Table 4
From table 4:
Navy blue reactive dye composition of the present invention has good moving and dyes and the level dyeing performance.
Embodiment 5
Colour fastness to perspiration
Be determined as follows as stated above the colour fastness to perspiration of dyestuff, test result is recorded in table 5
Table 5
From table 5:
Navy blue reactive dye composition of the present invention has excellent fastness to perspiration.
Embodiment 6
Fastness to soaping and color fastness to water
Be determined as follows as stated above fastness to soaping, color fastness to water and the color fastness to sea water of dyestuff, test result is recorded in table 6
Table 6
From table 6:
Navy blue reactive dye composition of the present invention has excellent fastness to soaping and color fastness to water.
Embodiment 7
Sunlight fastness
Be determined as follows as stated above the sunlight fastness of dyestuff, test result is recorded in table 7
Table 7
From table 7:
Navy blue reactive dye composition of the present invention still has good sunlight fastness.
Embodiment 8
The chlorinated water resist fastness
Be determined as follows as stated above the colour fastness to chlorinated water of dyestuff, test result is recorded in table 8
Table 8
From table 8, navy blue reactive dye composition of the present invention has good chlorinated water resist fastness, can effectively improve the poor problem of reference dyestuff chlorinated water resist fastness.
Claims (10)
1. a navy blue reactive dye composition, this dye composite contains the dye composition that dye composition that one or more general formulas (1) mean, dye composition that one or more general formulas (2) mean and one or more general formulas (3) mean:
In formula:
R
1For H ,-Cl, C
1-C
4Alkyl, C
1-C
4Alkoxyl group or-SO
3M;
Y
1For-CH
2CH
2OSO
3M or-CH=CH
2
M is H or alkali metal cation;
P is 0 or 1;
T is 0 or 1;
In formula:
Y
3And Y
4Be independently-CH respectively
2CH
2OSO
3M or-CH=CH
2
R
2, R
3, R
4And R
5Be H, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or sulfonic group;
M is H or alkali metal cation;
In formula:
T is-NHCOQ or-SO
2Y
2;
Q is-CHXCH
2X or-CX=CH
2
X is Cl or Br;
Y
2For-CH
2CH
2OSO
3M or-CH=CH
2
M is H, Na, K or NH
4 +Group;
R
6And R
7Be H, halogen, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or sulfonic group;
N is 0,1 or 2;
The dye composition that one or more general formulas (1) mean: the dye composition that one or more general formulas (2) mean: the weight ratio of the dye composition that one or more general formulas (3) mean is 20～60:20～55:5～60.
2. navy blue reactive dye composition claimed in claim 1, its characteristic is, the dye composition that one or more general formulas (1) mean: the dye composition that one or more general formulas (2) mean: the weight ratio of the dye composition that one or more general formulas (3) mean is 20～50:20～50:10～50.
3. navy blue reactive dye composition claimed in claim 1, its characteristic is, in general formula (1) left side-SO
3Contraposition or a position of be positioned on benzene nucleus-COO group of M group; The R of general formula (1) downside
1Group, when p=1, be positioned on benzene nucleus
Position or contraposition between group; The middle right side of general formula (1)-SO
2Y
1Ortho position or a position of be positioned on benzene nucleus-N=N-group of group; When t=1, the middle right side of general formula (1)-SO
3Position between be positioned on benzene nucleus-N=N-group of M group.
4. navy blue reactive dye composition claimed in claim 1, its characteristic is, the R in general formula (2)
2, R
3, R
4And R
5Ortho position or a position of be separately located in respectively on benzene nucleus-N=N-group of group; In general formula (2)-SO
2Y
3With-SO
2Y
4Position or contraposition between be separately located in respectively on benzene nucleus-N=N-group of group.
5. navy blue reactive dye composition claimed in claim 1, its characteristic is, the T group of general formula (3), contraposition or a position of be positioned on benzene nucleus-N=N-group; R
6Group and R
7Ortho position or a position of be separately located in respectively on benzene nucleus-N=N-group of group.
6. navy blue reactive dye composition claimed in claim 1, its characteristic is, general formula (3) left side-(SO
3M) n group, the ortho position of when n=1, be positioned on benzene nucleus-N=N-group, a position or contraposition; When n=2, ortho position and contraposition or ortho position and a position of be positioned on benzene nucleus-N=N-group; The NHCOQ group in left side in general formula (3), ortho position, a position or the contraposition of be positioned on benzene nucleus-N=N-group.
7. the described navy blue reactive dye composition of any one in claim 1～6, its characteristic is, the dye composition that general formula (1) means is:
8. the described navy blue reactive dye composition of any one in claim 1～6, its characteristic is, the dye composition that general formula (2) means is:
Dyestuff 2-6.
9. the described navy blue reactive dye composition of any one in claim 1～6, its characteristic is, the dye composition that general formula (3) means is:
10. the application of the described navy blue reactive dye composition of any one aspect the dyeing of hydroxyl and/or formamido-material in claim 1～9.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100071997A CN102585553B (en) | 2011-01-14 | 2011-01-14 | Navy-blue reactive dye composition and dyeing application thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100071997A CN102585553B (en) | 2011-01-14 | 2011-01-14 | Navy-blue reactive dye composition and dyeing application thereof |
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| CN102585553B true CN102585553B (en) | 2013-12-04 |
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| CN105273438B (en) * | 2014-07-21 | 2018-02-06 | 上海安诺其集团股份有限公司 | A kind of dye composite |
| CN105315720B (en) * | 2014-07-21 | 2018-09-07 | 上海安诺其集团股份有限公司 | A kind of preparation method of dyestuff |
| CN104478770A (en) * | 2014-12-11 | 2015-04-01 | 吴江桃源染料有限公司 | Black reactive dye semi-finished product and preparation method and application thereof |
| CN105295443A (en) * | 2015-11-30 | 2016-02-03 | 无锡新德印染制品有限公司 | High-color fastness navy blue reactive dye composition |
| CN105566946A (en) * | 2015-12-22 | 2016-05-11 | 浙江亿得化工有限公司 | Composite reactive blue dye for wool and preparation method of composite reactive blue dye for wools |
| CN107313269B (en) * | 2017-06-28 | 2019-06-25 | 江苏安诺其化工有限公司 | A kind of application of dyestuff in dyeing |
| CN107189492A (en) * | 2017-06-28 | 2017-09-22 | 江苏安诺其化工有限公司 | A kind of dyestuff, dye composite and dye material composition |
| CN107325585B (en) * | 2017-06-28 | 2019-06-25 | 江苏安诺其化工有限公司 | A kind of preparation method of dyestuff |
| CN113667324A (en) * | 2021-09-07 | 2021-11-19 | 湖北华丽染料工业有限公司 | Dark blue reactive dye composition and preparation method thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH395382A (en) * | 1959-12-24 | 1965-07-15 | Geigy Ag J R | Process for the production of formazan dyes containing heavy metals |
| CH481190A (en) * | 1967-02-17 | 1969-11-15 | Geigy Ag J R | Process for the production of reactive formazan dyes containing heavy metals |
| JPS5792054A (en) * | 1980-11-28 | 1982-06-08 | Nippon Kayaku Co Ltd | Copper-containing reactive dye |
| DE19511688C2 (en) * | 1995-03-30 | 1999-07-22 | Dystar Textilfarben Gmbh & Co | Dye mixtures of fiber-reactive azo dyes and their use for dyeing fiber material containing hydroxyl and / or carbonamide groups |
| DE19511689A1 (en) * | 1995-03-30 | 1996-10-02 | Hoechst Ag | Mixture of blue-coloring fiber-reactive dyes and their use for dyeing fiber material containing hydroxyl and / or carbonamide groups |
| DE19640203A1 (en) * | 1996-09-30 | 1998-04-02 | Dystar Textilfarben Gmbh & Co | Mixtures of blue-dyeing fiber-reactive dyes and their use for dyeing fiber material containing hydroxyl and / or carbonamide groups |
| MY139986A (en) * | 2005-07-06 | 2009-11-30 | Ciba Sc Holding Ag | Mixtures of reactive dyes and their use |
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