CN102757667B - Red reactive dye composition and dyeing application thereof on fiber - Google Patents
Red reactive dye composition and dyeing application thereof on fiber Download PDFInfo
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Abstract
The invention provides a red reactive dye composition and a dyeing application thereof. The dye composition comprises 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 red reactive dye composition provided by the invention has excellent dyeing performance, various good dyeing fastness, and excellent compatibility in cooperation with other common yellow and blue reactive dyes.
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 red reactive dye composition and the tint applications on filamentary material thereof.
Background technology
Red reactive dyes and composition thereof are one of focuses of current dyestuff circle research and development.
Along with the specification of quality to cellulosic fibre and textile dyeing product thereof is more and more high, people are also day by day harsh to the requirement of reactive dyestuffs on properties for dyeing.For the reactive dyestuffs kind for commercial, usually adopt the mode of blending composition, improve and improve every dyeing behavior.
The dyestuff blending that the dyestuff that the dyestuff that red reactive dye composition of the present invention is meaned by general formula (1), general formula (2) mean and general formula (3) mean forms.
The dyestuff that general formula (1) means, its Representative Cultivars is the C.I. REACTIVE Red 195.
The structure of this kind, at first be published in the patent US4341699 (1982) that SUMITOMO CHEMICAL company applies for.It is red that this kind coloured light is blue light, has good dyefastness, and with low cost, thereby the concern on the boundary that extremely prints and dyes.
But regrettably, this kind dyeing kinetics is slow, reactivity is poor, enhancing rate is low, has a strong impact on the industrial application of this kind.Sumitomo company and Bayer company are improved the structure of this kind respectively later.These improvement are published in following patent:
US 5131917 (1992) (Sumitomo)
US 5324329 (1994) (Sumitomo)
US 5359040 (1994) (Sumitomo)
US 5428141(1995)(Bayer)
The beginning of this century, Dystar company adopts the mode of blending combination to improve some defect in above-mentioned dyeing application.Be published in US 6165231 (2000) (Dystar) patent recorded and narrated another component of adding, its representative structure that adds component is C.I. reactive red 198, the dyestuff that general formula of the present invention (2) means.
At first this dye species is published in the patent US 4725675 (1988) that Hoechst company delivers.Hoechst company also makes improvements this dye species and is perfect later.These improvement are published in following patent:
US 5250670(1993)(Hoechst)
US 5548072(1996)(Hoechst)
The inventor tests by a large amount of tint applications, the dye composite that US 6165231 (2000) (Dystar) is provided is investigated rear discovery, the composition kind of this dye composite each tool advantage and defect, some application performance of composition after blending, compare with its composition dyestuff, really be improved to some extent and improve.For example the dyeing kinetics of composition and enhancing rate, make moderate progress than forming one of dyestuff.But the space of improving is obviously not enough.
The inventor is by experimental study, find, the dyestuff that adds general formula of the present invention (3) expression at the aforesaid combination species, as the 3rd component, is adjusted the proportion of composing of each component pleasantly surprisedly, the red reactive dye composition made has very excellent application performance, obtains gratifying effect.
The tint applications performance of red reactive dye composition of the present invention and every dyefastness, not only be better than the red reactive dye composition that US 6165231 (2000) (Dystar) provides, and also be better than the red reactive dye composition of being correlated with US 5980590 (1999) (Dystar) and US 6136045 (2000) (Dystar) provides.
The red reactive dye composition of the present invention's three components is not seen in the patent report so far.
Summary of the invention
The inventor, by experimental study, is surprised to find the red reactive dyes compound that contains one or more general formulas (1) and mean, the red reactive dyes compound of one or more general formulas (2) expression and the red dye composition of the red reactive dyes compound that one or more general formulas (3) mean and has very excellent dyeing behavior and every fastness.
What be worth proposition is, red reactive dye composition of the present invention is compared with one or more red reactive dyes that general formula (1) means, and general formula (1) dyestuff (Dystar) provided with US 6165231 (2000) compares with the dye composite that general formula (2) dyestuff forms, its enhancing rate, degree of fixation, consistency all are significantly improved and improve.
Red 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:
Z
1for-CH
2cH
2oSO
3m or-CH=CH
2;
R
1and R
2be H, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group or-SO
3m;
R
3for H or C
1-C
4alkyl;
R
4for H or C
1-C
4alkyl;
X
1for Cl or F;
M is H or alkali metal cation;
P is 0 or 1;
General formula (2)
In formula:
Z
2for-CH
2cH
2oSO
3m or-CH=CH
2;
R
5and R
6be H, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group or sulfonic group;
R
7for H or C
1-C
4alkyl;
R
8and R
9be H, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group or sulfonic group;
X
2for Cl or F;
M is H or alkali metal cation.
General formula (3)
In formula:
Z
3and Z
4be independently-CH respectively
2cH
2oSO
3m or-CH=CH
2; ;
R
10and R
11be H, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group or sulfonic group;
R
12for H or C
1-C
4alkyl;
R
13and R
14be H, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group or sulfonic group;
X
3for Cl or F;
M is H or alkali metal cation.
The present invention also provides the application of above-mentioned red reactive dye composition at the dyeing aspect of hydroxyl and/or formamido-material, particularly filamentary material.
Specific implementation method
In red reactive dye composition 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: 30～65: 5～50: 5～50, be preferably 40～55: 10～45: 10～45, more preferably 45～50: 10～45: 10～45.
One preferred embodiment in, in general formula (1)-SO
2z
1group is positioned on benzene nucleus
the contraposition of group or a position; R
1and R
2be separately located on benzene nucleus respectively
the ortho position of group, contraposition or a position.
Another preferred embodiment in, (SO in general formula (1)
3m)
pgroup, when the diazo component main body is benzene nucleus, p equals 0, R
4contraposition or a position of be positioned on benzene nucleus-N=N-group of group; When the diazo component main body is naphthalene core, when p=1, sulfonic acid group is positioned at 5 of naphthalene core, R
4be positioned at 4,5,6 or 7 on naphthalene core.
One preferred embodiment in, in general formula (2) left side-SO
2z
2group, ortho position, a position or the contraposition of be positioned on benzene nucleus-N=N-group.The R in left side in general formula (2)
5and R
6group, ortho position, a position or the contraposition of be separately located in respectively on benzene nucleus-N=N-group.
Another preferred embodiment in, general formula (2) right side-SO
3the M group, be positioned on benzene nucleus
the contraposition of group, a position or ortho position; The R on right side in general formula (2)
8and R
9group, be separately located on benzene nucleus respectively
the contraposition of group, a position or ortho position.
One preferred embodiment in, in general formula (3) left side-SO
2z
3group, ortho position, a position or the contraposition of be positioned on benzene nucleus-N=N-group; The R in left side in general formula (3)
10and R
11group, ortho position, a position or the contraposition of be separately located in respectively on benzene nucleus-N=N-group.
Another preferred embodiment in, in general formula (3) right side-SO
2z
4group, be positioned on benzene nucleus
the ortho position of group, a position or contraposition; The R on right side in general formula (3)
13and R
14group, be separately located on benzene nucleus respectively
the ortho position of group, a position or contraposition.
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
Dyestuff I-6
Dyestuff I-7 or
Dyestuff I-8.
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
Dyestuff 2-6
Dyestuff 2-7 or
Dyestuff 2-8.
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.
US 4341699 (1982) (Sumitomo), US 5131917 (1992) (Sumitomo) and JP 5117538 (1992) (Sumitomo) disclose dye structure and synthetic method thereof that general formula (1) means.
US 4725675 (1988) (Hoechst) has announced dye structure and the synthetic method thereof that general formula (2) means.
US 5250670 (1993) (Hoechst), US 5292870 (1994) (ICI), US 5665124 (1997) (Bayer) and CN 1503828 (2004) (Ke Laienante finance (BVI) company limited), US7091328 (2006) (Clariant Finanace (BVI) Limited) announced dye structure and synthetic method thereof that general formula (3) means.
The full content of above-mentioned document is referred in the present invention.
Red 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, generally 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 red 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.
Red 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.
Red 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, Salt And Alkali Tolerance solubleness: take a certain amount of dyestuff, add distilled water 65mL to be configured to dye liquor in the 250mL Erlenmeyer flask.Erlenmeyer flask is put in the vibration dyeing machinery, after 60 ℃ of insulation 5min, adds 200g/L Na
2sO
425mL, continue to add 200g/LNa after insulation 5min
2cO
310mL, then carry out suction filtration (during suction filtration, pressure 0.075Mpa, 5A qualitative filter paper) after being incubated 30min, observe the filter paper residual condition.Reduce dye strength (G/L), until residual without dyestuff on filter paper, the Salt And Alkali Tolerance that dye strength now (G/L) is dyestuff dissolves.
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 red 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 | 45% dyestuff 1-1+10% dyestuff 2-1+45% 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 | 45% dyestuff 1-1+10% dyestuff 2-2+45% 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 Z | 50% dyestuff 2-1+50% dyestuff 3-1 |
| 10 | Reference U | 100% dyestuff 1-1 |
| 11 | Reference V | 100% dyestuff 2-1 |
*reference X is (Dystar) cited embodiment of US 6165231 (2000).
*reference Y is (Dystar) cited embodiment of US 6136045 (2000).
*reference Z is (Dystar) cited embodiment of US 5980590 (1999).
Embodiment 1
Enhancing rate test (the K/S value at absorbing wavelength 520nm 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:
Red reactive dye composition of the present invention, compare with the reference dyestuff, and its enhancing rate increases significantly.
Embodiment 2
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 red reactive dye composition of the present invention is compared with the reference dyestuff, be improved to some extent, thereby improved because of the reference dye affinity too lowly, easily produced the shortcoming of migration, shown, red yellow with conventional three primary colors good consistency when dying;
2) red reactive dye composition of the present invention is compared degree of exhaustion with the reference dyestuff and is improved.
Embodiment 3
The test of Salt And Alkali Tolerance solubleness
Be determined as follows as stated above the Salt And Alkali Tolerance solubleness of dyestuff, test result is recorded in table 4
Table 4
From table 4:
The Salt And Alkali Tolerance solubleness of red reactive dye composition of the present invention is better than the reference dyestuff, thereby has good level dyeing performance.
Embodiment 4
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:
Red reactive dye composition of the present invention has good fastness to perspiration.
Embodiment 5
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:
Red reactive dye composition of the present invention has good fastness to soaping and color fastness to water.
Embodiment 6
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:
Red reactive dye composition of the present invention still has good sunlight fastness.
Embodiment 7
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, red 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 (11)
1. a red 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:
Z
1for-CH
2cH
2oSO
3m or-CH=CH
2;
R
1and R
2be H, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group or-SO
3m;
R
3for H or C
1-C
4alkyl;
R
4for H or C
1-C
4alkyl;
X
1for Cl or F;
M is H or alkali metal cation;
P is 0 or 1;
In formula:
Z
2for-CH
2cH
2oSO
3m or-CH=CH
2;
R
5and R
6be H, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group or sulfonic group;
R
7for H or C
1-C
4alkyl;
R
8and R
9be H, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group or sulfonic group;
X
2for Cl or F;
M is H or alkali metal cation;
In formula:
Z
3and Z
4be independently-CH respectively
2cH
2oSO
3m or-CH=CH
2;
R
10and R
11be H, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group or sulfonic group;
R
12for H or C
1-C
4alkyl;
R
13and R
14be H, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group or sulfonic group;
X
3for Cl or F;
M is H or alkali metal cation;
The dye composition that one or more general formulas (1) mean: the dye composition that one or more general formulas (2) mean: the dye composition that one or more general formulas (3) mean weight ratio be 30～65:5～50:5～50.
2. red 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 dye composition that one or more general formulas (3) mean weight ratio be 40～55:10～45:10～45.
3. red reactive dye composition claimed in claim 1, its characteristic is, in general formula (1)-SO
2z
1group is positioned on benzene nucleus
the contraposition of group or a position; R
1and R
2be separately located on benzene nucleus respectively
the ortho position of group, contraposition or a position.
4. red reactive dye composition claimed in claim 1, its characteristic is that the left nitrogen component that stresses of general formula (1) is benzene nucleus or naphthalene nuclear derivatives; General formula (1) is left when stressing nitrogen component main body and being benzene nucleus, and p equals 0, R
4contraposition or a position of be positioned on benzene nucleus-N=N-group of group; When general formula (1) is left when stressing nitrogen component main body and being naphthalene core, when p=1, sulfonic acid group is positioned at 5 of naphthalene core, R
4group is positioned at 4,6 or 7 on naphthalene core.
5. red reactive dye composition claimed in claim 1, its characteristic is, in general formula (2) left side-SO
2z
2group, ortho position, a position or the contraposition of be positioned on benzene nucleus-N=N-group, the R in left side in general formula (2)
5and R
6ortho position, a position or the contraposition of be separately located in respectively on benzene nucleus-N=N-group of group.
6. red reactive dye composition claimed in claim 1, its characteristic is, general formula (2) right side-SO
3the M group, be positioned on benzene nucleus
the contraposition of group, a position or ortho position; The R on right side in general formula (2)
8and R
9group, be separately located on benzene nucleus respectively
the contraposition of group, a position or ortho position.
7. red reactive dye composition claimed in claim 1, is characterized in that, the middle left side of general formula (3)-SO
2z
3group, ortho position, a position or the contraposition of be positioned on benzene nucleus-N=N-group; The R in left side in general formula (3)
10and R
11group, ortho position, a position or the contraposition of be separately located in respectively on benzene nucleus-N=N-group.
8. red reactive dye composition claimed in claim 1, is characterized in that, the middle right side of general formula (3)-SO
2z
4group, be positioned on benzene nucleus
the ortho position of group, a position or contraposition; The R on right side in general formula (3)
13and R
14group, be separately located on benzene nucleus respectively
the ortho position of group, a position or contraposition.
9. the described red reactive dye composition of claim 1～8, its characteristic is, the dye composition that general formula (1) means is:
The dye composition that general formula (2) means is:
The dye composition that general formula (3) means is:
10. the application of the described red reactive dye composition of any one aspect the dyeing of hydroxyl and/or formamido-material in claim 1～9.
11. application as claimed in claim 10, wherein hydroxyl and/or formamido-material are hydroxyl and/or formamido-filamentary material.
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|---|---|---|---|
| CN 201110105159 CN102757667B (en) | 2011-04-26 | 2011-04-26 | Red reactive dye composition and dyeing application thereof on fiber |
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|---|---|---|---|
| CN 201110105159 CN102757667B (en) | 2011-04-26 | 2011-04-26 | Red reactive dye composition and dyeing application thereof on fiber |
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|---|---|---|---|---|
| CN103554976A (en) * | 2013-09-29 | 2014-02-05 | 天津德凯化工股份有限公司 | Red reactive dye and preparation method thereof |
| CN103554980A (en) * | 2013-09-29 | 2014-02-05 | 天津德凯化工股份有限公司 | Red reactive dye and preparation method thereof |
| CN103554981A (en) * | 2013-09-29 | 2014-02-05 | 天津德凯化工股份有限公司 | Red reactive dye |
| CN103540160B (en) * | 2013-10-18 | 2015-12-30 | 大连理工大学 | Containing the red azo class reactive dyestuffs of sulfanilamide structure |
| CN104312201A (en) * | 2014-09-28 | 2015-01-28 | 天津德凯化工股份有限公司 | Red reactive dye for nylon |
| CN104277492A (en) * | 2014-09-28 | 2015-01-14 | 天津德凯化工股份有限公司 | Reactive red dye and preparation method thereof |
| CN104479402A (en) * | 2014-12-11 | 2015-04-01 | 吴江桃源染料有限公司 | Semi-finished product of deep red dye, preparation method and application thereof |
| CN104774484B (en) * | 2014-12-29 | 2017-02-22 | 浙江科永化工有限公司 | Reactive red dye composition |
| CN105602286B (en) * | 2016-03-17 | 2017-12-12 | 浙江瑞华化工有限公司 | A kind of Black reactive dye composition and its production and use |
| CN116004032A (en) * | 2022-12-30 | 2023-04-25 | 上海雅运新材料有限公司 | Red dye compound and synthetic method and application thereof |
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| US4341699A (en) * | 1979-07-13 | 1982-07-27 | Sumitomo Chemical Company, Limited | Reactive red dye having both monochlorotriazinyl- and vinylsulfone-type reactive groups |
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| GB2239871B (en) * | 1989-12-11 | 1993-03-10 | Sumitomo Chemical Co | Fiber reactive red dye composition |
| TW274097B (en) * | 1991-09-27 | 1996-04-11 | Hoechst Ag | |
| JP3116461B2 (en) * | 1991-10-24 | 2000-12-11 | 住友化学工業株式会社 | Monoazo compound and method for dyeing or printing fiber material using the same |
| US5428141A (en) * | 1991-12-05 | 1995-06-27 | Bayer Aktiengesellschaft | Azo dyestuffs containing fluorotriazinyl and vinylsulfonylmethyl-type reactive groups |
| JP3198635B2 (en) * | 1992-06-26 | 2001-08-13 | 住友化学工業株式会社 | Reactive dye mixture and dyeing or printing method using the same |
| DE4320151A1 (en) * | 1993-06-17 | 1994-12-22 | Hoechst Ag | Water-soluble azo compounds, process for their preparation and their use as dyes |
| US5980590A (en) * | 1995-12-28 | 1999-11-09 | Dystar Texilfarben Gmbh & Co. Deutschland Kg | Dyestuff mixtures of water-soluble fiber-reactive azo dyestuffs, processes for their preparation and their use |
| DE19836661A1 (en) * | 1998-08-13 | 2000-02-17 | Dystar Textilfarben Gmbh & Co | Dye mixture of water-soluble fiber-reactive azo dyes, process for their preparation and their use |
| DE19852051A1 (en) * | 1998-11-11 | 2000-05-18 | Dystar Textilfarben Gmbh & Co | Dye mixture, process for their preparation and their use |
| DE19922826A1 (en) * | 1999-05-19 | 2000-11-23 | Dystar Textilfarben Gmbh & Co | Orange and scarlet mixtures of reactive dyes |
| CN101323709B (en) * | 2007-06-11 | 2011-05-04 | 上海雅运纺织化工有限公司 | Red reactive dye composition and dyeing application thereof to fibre material |
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