CN102115612B - Dark blue active dye composition and application thereof in dyeing fibers - Google Patents
Dark blue active dye composition and application thereof in dyeing fibers Download PDFInfo
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- CN102115612B CN102115612B CN200910247502.3A CN200910247502A CN102115612B CN 102115612 B CN102115612 B CN 102115612B CN 200910247502 A CN200910247502 A CN 200910247502A CN 102115612 B CN102115612 B CN 102115612B
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Abstract
The invention provides a dark blue active dye composition and application thereof in dyeing fibers. The dye composition comprises one or more of dye compounds shown in a general formula (1), and one or more of dye compounds shown in a general formula (2). The dark blue active dye composition has excellent dyeing property and various items of dyefastness, and excellent compatibility with other common red and yellow active dyes. Substituent groups in the general formulas (1) and (2) are shown in the specifications.
Description
Technical field
The present invention relates to a kind of reactive dye compositions and in the tint applications of filamentary material, particularly relate to dark blue active dye composition and the tint applications on filamentary material thereof.
Background technology
The development research of mazarine reactive dyestuffs is one of current dye industry focus of attention always.This is not only because blueness consumption in all tones is maximum, and it is again the main ingredient of blending black reactive dye compositions or mixture.
Along with day by day harsh to the requirement of printed fabrics, mazarine reactive dyestuffs must have the fastness of various excellences concurrently, but also should have good application performance, for example dye uptake, enhancing, degree of fixation and consistency.
Blue active dye shown in general formula of the present invention (1) has a kind of first of copper-containing metal
class (Formazan) dyestuff.Last century, late nineteen eighties the early 1990s ，Ge major company delivered relevant patent, announced its molecular structure and synthetic method thereof.These patents are:
US 4,720,542 (1988) (Sumitomos)
US 4,880,434 (1989) (Sumitomos)
US 5,076,811(1991)(Cola-Geigy)
Blue active dye shown in general formula (1) is with its excellent light fastness and the extremely concern of dyestuff circle of sweat proof light fastness.But have to be pointed out that, the blue active dye shown in this class general formula (1) also has many defects, has a strong impact on and limit its widespread use.These defects are that solubleness is not high, level-dyeing property, and the application performances such as enhancing and degree of fixation are not ideal enough.
In recent years, each major company of the world forms new dark blue active dye composition to blue active dye shown in above-mentioned general formula (1) or mixture conducts extensive research.
The patent of delivering thus has:
US 6,171,348(2001)(Dystar)
JP 11071534 (1999) (Sumitomo)
JP 4314763 (1992) (Sumitomo)
JP 1103668 (1989) (Mitsubishi changes into)
JP 804903 (1996) (Mitsubishi changes into)
CN 4,888,028(1989)(Mitsubishi Kasei)
CN 101193984(2008)(Dystar)
Other combination dyestuff that above-mentioned patent is announced, is respectively anthraquinone type, triphendioxazine type, azo-type and first
type reactive dyestuffs.
Yet, in above-mentioned patent, still solve unsatisfactorily above-mentioned colorant dissolubility not high, its level-dyeing property, the dissatisfactory problem of the application performances such as enhancing and degree of fixation.Therefore, in the urgent need to a kind of comprehensive tint applications performance of this dyestuff and fastness of making, all need further to be improved and improved dye product.
Summary of the invention
The inventor is by experimental study, be surprised to find the dye composite that one or more mazarine reactive dye compounds of general formula (1) expression and one or more mazarine reactive dye compounds of general formula (2) expression form, there is very excellent dyeing behavior and every fastness.
What be worth proposition is, this dark blue active dye composition is compared with its composition dyestuff, not only keeps the part fastness of the original excellence of dyestuff shown in general formula (1), and significantly improves its degree of fixation, enhancing and consistency, thus its Application Areas effectively expanded.
The dye composition that one or more general formulas (1) shown in being selected from below that dark blue active dye composition provided by the invention comprises that certain proportion mixes represent and a kind of formula is multiple dye composition that general formula (2) shown in being selected from below represents:
General formula (1)
In formula:
R
1for H, Cl, C
1-C
4alkoxyl group is as-OCH
3, C
1-C
4alkyl is as-CH
3,-SO
3m;
R
5for C
1-C
4alkyl;
R
6and R
7be H, halogen, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group or sulfo group;
Y
1for CH
2cH
2oSO
3m or-CH=CH
2;
X be Cl, F or
P is 0,1 or 2;
M is 0 or 1;
T is 0 or 1;
M be H, Na, K or-NH
4group;
General formula (2)
In formula:
T is-NHCOQ or-SO
2y
2;
Q is-CHX
1cH
2x
1or-CX
1=CH
2;
X
1for Cl or Br;
Y
2for-CH
2cH
2oSO
3m or-CH=CH
2;
R
2and R
3be H, halogen, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group or sulfonic group;
R
4for sulfonic group;
N is 0,1 or 2;
M be H, Na, K or-NH
4group.
The present invention also provides above-mentioned dark blue active dye composition in cotton, the application that dyeability ofwool fabric is tattooed the face.
Dark blue active dye composition provided by the invention has excellent dyeing behavior and every dyefastness, and conventional red with other, the excellent consistency that Yellow active dye dyes altogether.
Specific implementation method
Dye composite of the present invention comprises the dye composition of one or more general formulas (1) expression and the dye composition that one or more general formulas (2) represent, but the dye composition of the dye composition that it also can be represented by one or more general formulas (1) and one or more general formulas (2) expression forms.
In dye composite of the present invention, the dye composition that general formula (1) represents (being called for short dyestuff I) is 90～10: 10～90 with the weight ratio of the dye composition (being called for short dyestuff II) that general formula (2) represents, be preferably 80～20: 20～80, more preferably 70～30: 30～70, most preferably be 60～40: 40～60.
One preferred embodiment in, general formula (1) right side-SO
2y group, is positioned on benzene nucleus
the contraposition of group or a position.The R on general formula (1) right side
6and R
7group is separately located on benzene nucleus respectively
the ortho position of group, a position and contraposition.
Another preferred embodiment in, in general formula (1) left side-SO
3m group, contraposition or a position of when p=1, be positioned on benzene nucleus-COO group; When p=2, ortho position and the contraposition of be positioned on benzene nucleus-COO group.
One preferred embodiment in, general formula (1) middle part-SO
3m group, when m=1, be positioned on benzene nucleus-N=N-group ask Wei Huo Ling position.General formula (1) middle part-NH-group, ortho position or a position of be positioned on benzene nucleus-O-group.
Another preferred embodiment in, the R of general formula (1)
1group, when t=1, is positioned on benzene nucleus
position or contraposition between group.T group in general formula (2), ortho position or the contraposition of be positioned on benzene nucleus-N=N-group; R in general formula (2)
2and R
3ortho position, a position or the contraposition of be separately located in respectively on benzene nucleus-N=N-group of group.
One preferred embodiment in, R in general formula (2)
4group, ortho position, a position or the contraposition of be positioned on benzene nucleus-N=N-group; In general formula (2)-NHCOQ group, ortho position, a position or the contraposition of be positioned on benzene nucleus-N=N-group.
Another preferred embodiment in, in general formula (2)-the Q group of NHCOQ group, be selected from-CHXCH
2x or-CX=CH
2group, wherein the halogen of X, is preferably Br.
In general formula (1) and general formula (2), p is preferably 0 or 1; M is preferably 1; N is preferably 0 or 1; T is preferably 1; M is preferably Na or K.
In this application, C
1-C
4alkyl represents the alkyl that contains 1-4 carbon atom, as methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl or the tertiary butyl.C
1-C
4alkoxyl group represents the alkoxyl group that contains 1-4 carbon atom, as methoxyl group, oxyethyl group, positive propoxy, isopropoxy, n-butoxy, sec-butoxy or tert.-butoxy.Halogen represents fluorine, chlorine, bromine and iodine, preferably chlorine or bromine.
In the present invention, the dyestuff that general formula (1) represents, for example, comprise following example:
Dyestuff I-1
Dyestuff I-2
Dyestuff I-3
Dyestuff I-4
Dyestuff I-5
Dyestuff I-6
Dyestuff I-7
Dyestuff I-8
In the present invention, the dyestuff that general formula (2) represents, for example, comprise following example:
Dyestuff II-1
Dyestuff II-2
Dyestuff II-3
Dyestuff II-4
Dyestuff II-5
Dyestuff II-6
Dyestuff II-7 or
Dyestuff II-8.
The reactive dyestuffs that general formula (1) and general formula (2) represent are known dye.
Structure and the synthetic method of the reactive dyestuffs that general formula (1) represents, see following patent:
JP 57092054 (1982) (chemical drug)
US 4,720,542 (1988) (Sumitomos)
US 4,935,500 (1990) (Sumitomos)
Structure and the synthetic method of the reactive dyestuffs that general formula (2) represents, see following patent:
US 6537332(2003)(Ciba Speciality Chemicals Corp.)
US 5,849,887(1998)(Ciba Speciality Chemicals Corp.)
CN 101215427 (2008) (Tianjin De Kai company)
CN 10148133 (2009) (Tianjin De Kai company)
CN 101481530 (2009) (Tianjin De Kai company)
The full content of above-mentioned document is referred in the present invention.
Dark blue active 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, is generally 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 substantially by general formula (1) dyestuff of above-mentioned weight ratio with general formula (2) dyestuff forms or be comprised of general formula (1) dyestuff and general formula (2) dyestuff of above-mentioned weight ratio.
The preparation method of dark blue active dye composition of the present invention comprises above-mentioned general formula (1) dyestuff and general formula (2) dyestuff weight ratio is in accordance with regulations mixed.Mix available various ordinary method, as mechanically mixing method.During mixing, general formula (1) dyestuff and general formula (2) 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.
Dark blue active 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.
Dark blue active dye composition of the present invention can be applied to filamentary material and be fixed on fiber by several different methods as known in the art, for example, can dye 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, Salt And Alkali Tolerance solubleness: take a certain amount of dyestuff, add distilled water 65mL to be configured to dye liquor in 250mL Erlenmeyer flask.Erlenmeyer flask is put in vibration dyeing machinery, after 60 ℃ of insulation 5min, adds 200g/LNa2SO4 25mL, continue to add 200g/LNa2CO3 10mL after insulation 5min, after being incubated again 30min, carry out suction filtration (during suction filtration, pressure 0.075Mpa, 5A qualitative filter paper), observe 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.
2, 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 fabric weight).After dyeing, fabric, after fixed temperature and humidity is processed, is tested its Apparent Depth K/S value record with Datacolor color measurement instrument.
3, degree of fixation test: dye liquor preparation, press 60 ℃ of constant temperature dyeings of reactive dyestuffs.After dyeing finishes, the cloth specimen in B dye bath is carried out to washing according to the following steps, and by dyeing residual liquid, the washing raffinate of each step concentrates on constant volume in the volumetric flask of a 500mL.When B dye bath cloth specimen carries out soap boiling, in A dye bath, also add the detergent of same amount to carry out soap boiling.A dye bath is cooled to room temperature after soaping and finishing, and constant volume is 500mL.A after constant volume, B dyeing residual liquid are diluted to certain multiple MA, MB, test absorptance values XA, the XB of its diluent when maximum absorption wavelength (XA, XB should between 0.2～0.7).
Degree of fixation=(1-XBMB/XAMA) * 100%
4, just dye rate and degree of exhaustion test: 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 comparison before dyeing.
Just dye rate=(1-adds the absorbance of the front dye liquor of absorbance/dyeing of the front dye liquor of alkali) * 100%
Degree of exhaustion=(1-soap before before the absorbance/dyeing of dye liquor the absorbance of dye liquor) * 100%
5, 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 B cloth specimen, 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 the color strength (K/S) * 100% of color strength (the K/S)/B cloth specimen of staining index MI=C cloth specimen
6, colour fastness to chlorinated water test: measure by international standard ISO 105 E03.
7, colour fastness to perspiration test: measure by international standard ISO 105-E04.
8, fastness to soaping test: measure by international standard ISO 105-C10.
9, color fastness to water test: measure by international standard ISO 105-E01.
10, color fastness to sea water test: measure by international standard ISO 105-E02.
11, colour fasteness to sunlight test: measure by international standard ISO 105-B02.
12, the photochromic fastness test of sweat proof: press Nippon Standard JIS L0888 and measure.
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 dark blue active dye compositions of the preparation embodiment of the present invention.
" % " in table 1 all represents % by weight, and the gross weight of dye composite of take is benchmark.
Table 1
| Numbering | Reactive dyestuffs title | Form |
| 1 | A | 70% dyestuff I-1+30% dyestuff II-1 |
| 2 | B | 50% dyestuff I-1+50% dyestuff II-1 |
| 3 | C | 30% dyestuff I-1+70% dyestuff II-1 |
| 4 | D | 70% dyestuff I-5+30% dyestuff II-6 |
| 5 | E | 50% dyestuff I-5+50% dyestuff II-6 |
| 6 | F | 30% dyestuff I-5+70% dyestuff II-6 |
| 7 | Reference W | 100% dyestuff I-1 |
| 8 | Reference X | 100% dyestuff I-5 |
| 9 | Reference Y | 100% dyestuff II-1 |
| 10 | Reference Z | 100% dyestuff II-6 |
Embodiment 1
The coloured light of dark blue active dye composition of the present invention
The dyestuff color and luster that general formula (I) represents is sky blue, and the dyestuff color and luster that general formula (II) represents is ruddiness blueness.
The coloured light of reactive dye compositions of the present invention can be adjusted the ratio of general formula (I) dyestuff and general formula (II) dyestuff as required, thereby makes mixture effectively form three primary colors combination with other redness, yellow dyes, improves its actual application value.
Embodiment 2
The test of Salt And Alkali Tolerance solubleness
The Salt And Alkali Tolerance solubleness that is determined as follows as stated above dyestuff, test result is recorded in table 2
Table 2
From table 2:
Dark blue active dye composition of the present invention, compares with the dyestuff that general formula (I) represents, its Salt And Alkali Tolerance solubleness significantly improves, thereby has improved the level-dyeing property of general formula (I) expression dyestuff.
Embodiment 3
Enhancing rate test (the K/S value at absorbing wavelength 620nm place)
The enhancing rate that is determined as follows as stated above dyestuff, test result is recorded in table 3
Table 3
From table 3:
1) dark blue active dye composition of the present invention, compares with the dyestuff that general formula (I) represents, its enhancing rate significantly improves;
2) the enhancing rate measured value of dark blue active dye composition of the present invention, is much higher than the weighted mean that it forms dyestuff, has embodied the effect of compound synergic.
Embodiment 4
Degree of fixation is measured
The degree of fixation that is determined as follows as stated above dyestuff, test result is recorded in table 4
Table 4
From table 4:
The degree of fixation measured value of dark blue active dye composition of the present invention, apparently higher than the weighted mean of its composition dyestuff, has embodied the effect of compound synergic.
Embodiment 5
Just dying rate and degree of exhaustion measures
First rate and the degree of exhaustion of dying that is determined as follows as stated above dyestuff, test result is recorded in table 5
Table 5
From table 5:
1) the first rate of dying of dark blue active dye composition of the present invention is compared with dyestuff I-5 with degree of exhaustion, all makes moderate progress, and shows, red yellow with conventional three primary colors good consistency when dying;
2) dark blue active dye composition of the present invention greatly reduces the first rate of dying of dyestuff I-5, and has avoided dying on dyestuff the too fast look flower phenomenon causing, and has improved level-dyeing property;
Embodiment 6
Moving staining index measures
The staining index that moves that is determined as follows as stated above dyestuff, test result is recorded in table 6
Table 6
From table 6:
Dark blue active dye composition of the present invention has good moving and dyes and level dyeing performance, compares with the reactive dyestuffs that general formula (I) represents, has greatly improved its migration property.
Embodiment 7
Chlorinated water resist fastness
The colour fastness to chlorinated water that is determined as follows as stated above dyestuff, test result is recorded in table 7
Table 7
From table 7:
Dark blue active dye composition of the present invention has good chlorinated water resist fastness, can effectively improve the poor problem of dyestuff I-3 chlorinated water resist fastness.
Embodiment 8
Colour fastness to perspiration
The colour fastness to perspiration that is determined as follows as stated above dyestuff, test result is recorded in table 8
Table 8
From table 8:
Dark blue active dye composition of the present invention has excellent fastness to perspiration.
Embodiment 9
Fastness to soaping, color fastness to water and color fastness to sea water
The fastness to soaping, color fastness to water and the color fastness to sea water that are determined as follows as stated above dyestuff, test result is recorded in table 9
Table 9
From table 9:
Dark blue active dye composition of the present invention has excellent fastness to soaping, color fastness to water and color fastness to sea water.
Embodiment 10
Sunlight fastness
The sunlight fastness that is determined as follows as stated above dyestuff, test result is recorded in table 10
Table 10
From table 10:
Dark blue active dye composition of the present invention still keeps the feature of dyestuff I-3, has good sunlight fastness.
Embodiment 11
The photochromic fastness of sweat proof
The photochromic fastness of sweat proof that is determined as follows as stated above dyestuff, test result is recorded in table 11
Table 11
From table 11:
Dark blue active dye composition of the present invention still keeps the feature of dyestuff I-1, has good sweat proof light fastness.
By above embodiment, can draw to draw a conclusion:
1), dark blue active dye composition of the present invention, significantly improved the shortcoming that general formula (I) represents dyestuff Salt And Alkali Tolerance poor solubility;
2), dark blue active dye composition of the present invention, the dyestuff representing with general formula (I) is compared, its enhancing rate significantly improves, and has improved general formula (I) and has represented the poor shortcoming of dyestuff depth;
3), dark blue active dye composition of the present invention, its degree of fixation measured value, the weighted mean that forms dyestuff apparently higher than it, has embodied the effect of compound synergic;
4), dark blue active dye composition of the present invention, it just dyes rate compares with the dyestuff that general formula (I) represents with degree of exhaustion, has clear improvement, and shows, red yellow with conventional three primary colors good consistency while dying together;
5), dark blue active dye composition of the present invention, effectively improved the poor shortcoming of migration property that general formula (I) represents dyestuff, have that good moving dyed and level dyeing performance;
6), dark blue active dye composition of the present invention, can effectively improve general formula (I) and represent the poor problem of dyestuff chlorinated water resist fastness;
7), dark blue active dye composition of the present invention has excellent colour fastness to perspiration, fastness to soaping, color fastness to water and color fastness to sea water;
8), dark blue active dye composition of the present invention still keeps general formula (I) to represent the advantage of dyestuff, has the photochromic fastness of good sunlight fastness and sweat proof.
Claims (10)
1. a dark blue active dye composition, the dye composition that the dye composition that this dye composite is represented by the general formula (1) shown in one or more are selected from below and one or more general formula (2) shown in being selected from below represents and the optional conventional dye additive using in dyeing and dye formulations form:
General formula (1)
In formula:
R
1for H, Cl, C
1-C
4alkoxyl group, C
1-C
4alkyl ,-SO
3m;
R
5for C
1-C
4alkyl;
R
6and R
7be H, halogen, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group or sulfo group;
Y
1for CH
2cH
2oSO
3m or-CH=CH
2;
X be Cl, F or
P is 0,1 or 2;
M is 0 or 1;
T is 0 or 1;
M be H, Na, K or-NH
4group;
General formula (2)
In formula:
T is-NHCOQ or-SO
2y
2;
Q is-CHX
1cH
2x
1;
X
1for Br;
Y
2for-CH
2cH
2oSO
3m or-CH=CH
2;
R
2and R
3be H, halogen, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group or sulfo group;
R
4for sulfo group;
N is 0,1 or 2;
M be H, Na, K or-NH
4group;
The weight ratio of the dyestuff that the dyestuff that general formula (1) represents and general formula (2) represent is 80～20:20～80.
2. dark blue active dye composition claimed in claim 1, its characteristic is, the dyestuff that general formula (1) represents is 70～30:30～70 with the weight ratio of the dyestuff of general formula (2) expression.
3. dark blue active dye composition claimed in claim 1, its characteristic is, in general formula (1) and general formula (2),
P is 0 or 1;
M is 1;
N is 0 or 1;
T is 1;
M be H, Na, K or-NH
4group.
4. dark blue active dye composition claimed in claim 1, its characteristic is, in general formula (1) left side-SO
3m group, contraposition or a position of when p=1, be positioned on benzene nucleus-COO group; When p=2, ortho position and the contraposition of be positioned on benzene nucleus-COO group; General formula (1) middle part-SO
3m group, ortho position or a position of when m=1, be positioned on benzene nucleus-N=N-group; General formula (1) middle part-NH group, ortho position or a position of be positioned on benzene nucleus-O-group.
5. dark blue active dye composition claimed in claim 1, its characteristic is, general formula (1) right side-SO
2y group, is positioned on benzene nucleus
the contraposition of group or a position, the R on general formula (1) right side
6and R
7group is separately located on benzene nucleus respectively
the ortho position of group, a position and contraposition.
6. dark blue active dye composition claimed in claim 1, its characteristic is, the R of general formula (1)
1group, when t=1, is positioned on benzene nucleus
position or contraposition between group.
7. dark blue active dye composition claimed in claim 1, its characteristic is, the T group of general formula (2), contraposition or a position of be positioned on benzene nucleus-N=N-group; R
2group and R
3ortho position, a position or the contraposition of be separately located in respectively on benzene nucleus-N=N-group of group.
8. dark blue active dye composition claimed in claim 1, its characteristic is, the R of general formula (2)
4group, ortho position or a position of be positioned on benzene nucleus-N=N-group; The NHCOQ group of general formula (2), position or contraposition between be positioned on benzene nucleus-N=N-group.
9. dark blue active dye composition claimed in claim 1, its characteristic is, the dye composition that general formula (1) represents is:
Dyestuff I-1
Dyestuff I-2
Dyestuff I-3
Dyestuff I-4
Dyestuff I-5
Dyestuff I-6
Dyestuff I-7 or
Dyestuff I-8
The dye composition that general formula (2) represents is:
Dyestuff II-1
Dyestuff II-2
Dyestuff II-3
Dyestuff II-4
Dyestuff II-6
Dyestuff II-7 or
Dyestuff II-8.
10. the application of the dark blue active dye composition described in any one aspect cotton, dyeability ofwool fabric in claim 1～9.
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|---|---|---|---|
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| CN103952013B (en) * | 2014-05-12 | 2016-03-16 | 浙江亿得化工有限公司 | A kind of compound reactive brilliant blue K-GR composition and use thereof and using method |
| CN105348854B (en) * | 2014-08-22 | 2017-03-22 | 湖北丽源科技股份有限公司 | Blue reactive dye |
| CN107345082A (en) * | 2016-05-05 | 2017-11-14 | 中山上如化工有限公司 | It is a kind of that there is the reactive dye compound for washing function of missing old times or old friends |
| CN108003656A (en) * | 2017-12-19 | 2018-05-08 | 天津德凯化工股份有限公司 | It is a kind of suitable for dark blue reactive dye of llama and preparation method thereof |
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| US6537332B1 (en) * | 1998-07-27 | 2003-03-25 | Ciba Speciality Chemicals Corporation | Reactive colorants, mixtures of reactive colorants and production and use thereof |
| CN101331194A (en) * | 2005-07-06 | 2008-12-24 | 亨斯迈先进材料（瑞士）有限公司 | Mixtures of reactive dyes and their use |
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2009
- 2009-12-30 CN CN200910247502.3A patent/CN102115612B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6537332B1 (en) * | 1998-07-27 | 2003-03-25 | Ciba Speciality Chemicals Corporation | Reactive colorants, mixtures of reactive colorants and production and use thereof |
| CN101331194A (en) * | 2005-07-06 | 2008-12-24 | 亨斯迈先进材料（瑞士）有限公司 | Mixtures of reactive dyes and their use |
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