CN102115613A - Blue reactive dye composition and dyeing application to fiber material thereof - Google Patents
Blue reactive dye composition and dyeing application to fiber material thereof Download PDFInfo
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- CN102115613A CN102115613A CN2009102475038A CN200910247503A CN102115613A CN 102115613 A CN102115613 A CN 102115613A CN 2009102475038 A CN2009102475038 A CN 2009102475038A CN 200910247503 A CN200910247503 A CN 200910247503A CN 102115613 A CN102115613 A CN 102115613A
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Abstract
The invention provides a blue reactive dye composition and a dyeing application to fiber materials thereof, and the dye composition comprises one or more than one compounds selected from the dye compounds represented in the following general formula (1) and one or more than one compounds selected from the dye compounds represented in the following general formula (2). The invention provides a blue reactive dye composition which has excellent dyeing application performance and every fastness when compared with the dye represented in general formula (1). Particularly, the fastness to chlorine, the solubility and the level-dyeing property of the blue reactive dye composition provided by the invention are significantly improved. Each substituent in general formula (1) and general formula (2) is as described in the description.
Description
Technical field
The present invention relates to a kind of reactive dye compositions and the tint applications on filamentary material thereof.Particularly, the present invention relates to a kind of blue active dye composition and the tint applications on filamentary material thereof.
Background technology
Reactive dyestuffs shown in the general formula that the present invention relates to (1) are the anthraquinone type blue active dye.These class reactive dyestuffs are good at the concern on the boundary that extremely prints and dyes with its lovely luster and good light fastness and sweat proof light fastness.
But the defective of this class dyestuff is its fastness to chlorine, and level-dyeing property and solubleness are unsatisfactory, is difficult to good consistency again and dyes together with the Huang of using always, red reactive dyes, thereby be difficult to satisfy the quality requirement of current printing and dyeing, limits its widespread use.
In recent years, new blue active dye composition or the mixture of the composition of the reactive dyestuffs shown in the mutual-through type (1) carried out broad research in this area.
The patent of delivering thus has:
1.JP 1103668 (1989) (Mitsubishi changes into company)
2.JP 64043568 (1989) (SUMITOMO CHEMICAL companies)
3.JP 2099564 (1990) (Mitsubishi changes into company)
4.JP 6192589 (1994) (SUMITOMO CHEMICAL companies)
5.JP 7207180 (1995) (Mitsubishi changes into company)
6.JP 8048903 (1996) (Mitsubishi changes into company)
7.US 5,456,726 (1995) (SUMITOMO CHEMICAL companies)
8.EP 905201 (1999) (Bezema companies)
9.CN 1580132 (2005) (Hua Bachang is dyed in Shanghai)
10.WO 2005/090485 (Ciba Specialty Chemicals Holding Inc)
11.CN 1934195 (2007) (Huntsman Advanced Materials Sw)
Other combination dyestuff that above-mentioned patent is announced is respectively Jia Za type, phthalocyanine type, triphendioxazine type, anthraquinone type and azo-type reactive dyestuffs.
Yet, still solving above-mentioned dyestuff fastness to chlorine in the above-mentioned patent unsatisfactorily, level-dyeing property and solubleness are unsatisfactory, are difficult to good consistency and Huang commonly used, the technical problem that red reactive dyes dyes together again.Therefore, pressing for a kind of comprehensive tint applications performance of this dyestuff and fastness of making further improves and improved dye product.
Summary of the invention
The inventor is by experimental study, the dye composite that one or more blue active dye compounds that are surprised to find general formula (2) expression and one or more blue active dye compounds of general formula (1) expression are formed has good dyeing behavior and every dyefastness the objective of the invention is to provide a kind of one or more blue active dye compounds of general formula (2) expression and dye composite of one or more blue active dye compounds that general formula (1) is represented of containing, and it has very excellent dyeing behavior and every fastness.
This dye composite is compared with one or more blue active dye compounds of general formula (1) expression, and its degree of fixation and enhancing rate obviously improve.Particularly importantly, this dye composite and other red, excellent compatibility that Yellow active dye dyes altogether commonly used.
Blue dyes composition provided by the invention comprise the certain proportion blended one or more be selected from below shown in general formula (1) expression dye composition and a kind of formula is multiple be selected from below shown in the dye composition of general formula (2) expression:
General formula (1)
In the formula:
R
1Be H, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, sulfo group, carboxyl or halogen;
R
2Be H, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, sulfo group or halogen;
Y
1For-CH
2CH
2OSO
3M ,-CH=CH
2,-CH
2CH
2OH or-CH
2CH
2Cl;
M be H, Na, K or-NH
4Group;
General formula (2)
In the 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
R
3And R
4Be H, halogen, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or sulfo group;
R
5Be sulfonic group;
N is 0,1 or 2;
M is H, Na, K or NH
4Group.
The present invention also provides above-mentioned blue active dye composition in cotton, the application in the wool fabric dyeing.
Blue active dye composition of the present invention has excellent dyeing behavior and every dyefastness, and commonly used red with other, the consistency of the excellence that Yellow active dye dyes altogether.
Specific implementation method
Comprise the dye composition of one or more general formulas (1) expression and the dye composition of one or more general formulas (2) expression in the dye composite of the present invention, it also can be made up of the dye composition of one or more general formulas (1) expression and the dye composition of one or more general formulas (2) expression.
In dye composite of the present invention, the dye composition of general formula (1) expression (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) of general formula (2) expression, be preferably 80～20: 20～80,70～30: 30～70,60～40: 40～60.
One preferred embodiment in, general formula (1) right side-SO
2Y group is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH group.R in the general formula (1)
1And R
2Group is separately located in respectively on the benzene nucleus-ortho position, a position or the contraposition of NH-group.
Another preferred embodiment in, the T group in the general formula (2) is positioned on the benzene nucleus-contraposition or a position of N=N-group.R in the general formula (2)
3And R
4Group is separately located in respectively on the benzene nucleus-ortho position, a position or the contraposition of N=N-group.
One preferred embodiment in, the R in the general formula (2)
5Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of N=N-group.
Another preferred embodiment in, in the general formula (2)-the NHCOQ group, be positioned on the benzene nucleus-ortho position, a position or the contraposition of N=N-group.
In general formula (1) and the general formula (2), R
1And R
2Preferred is H, C respectively independently
1-C
4Alkoxyl group, sulfo group or carboxyl; R
3And R
4Preferred is H, C respectively independently
1-C
4Alkyl, C
1-C
4Alkoxyl group or sulfo group; R
5Be preferably sulfo group; Y
1And Y
2Preferred difference is-CH independently
2CH
2OSO
3M or-CH=CH
2N is preferably 0 or 1; M is preferably Na or K group.
In this application, C
1-C
4Alkyl represents to contain the alkyl of 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 to contain the alkoxyl group of 1-4 carbon atom, as methoxyl group, oxyethyl group, positive propoxy, isopropoxy, n-butoxy, sec-butoxy or tert.-butoxy.Halogen is represented fluorine, chlorine, bromine and iodine, preferably chlorine or bromine.
Among the present invention, the dye composition of general formula (1) expression for example comprises 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
Among the present invention, the dye composition of general formula (2) expression for example comprises 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 of general formula (1) and general formula (2) expression are the known dye compound.
The reactive dyestuffs of general formula (1) expression are structure and the synthetic method thereof that well-known (C.I. Reactive Blue 19 100) many documents disclose these reactive dyestuffs, for example
CN 1580131 (2005) (Huayi (Group) Co., Shanghai)
The structure and the synthetic method thereof of the reactive dyestuffs of general formula (2) expression, see following patent:
US?6,537,332(2003)(Cita?Speciality?Chemicals?Corp.)
US?5,849,887(1998)(Cita?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 among the present invention.
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 by actual needs, and there is no particular limitation, generally is no more than 20 weight %.For example, electrolyte salt, as sodium sulfate or Repone K, content 0～10 weight %, preferred 2～6 weight %; The pH regulator agent, as SODIUM PHOSPHATE, MONOBASIC or Sodium phosphate dibasic, content 0～5 weight %, preferred 0.5～2.5 weight %, dust-proofing agent 0～10 weight %, preferred 0.1～2 weight %; Solubility promoter 1～15 weight %, preferred 0.1～3 weight %.The present composition also can be basically by general formula (1) dyestuff of above-mentioned weight ratio with general formula (2) dyestuff is formed or be made up of general formula (1) dyestuff and general formula (2) dyestuff of above-mentioned weight ratio.
The preparation method of 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 the 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 carry out in suitable shredder such as ball mill or needle mill and in kneader or mixing machine.
Blue active dye composition of the present invention is suitable for dyeing and various widely material thereof, the material that particularly contains 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.
Blue active dye composition of the present invention can be applied to filamentary material and is fixed on the fiber with several different methods as known in the art, for example can dye with dip-dye method or pad dyeing method.
Embodiment
Every testing method of embodiment
Every performance of present embodiment is tested by following every testing method
1, salt tolerant alkali solubility: take by weighing a certain amount of dyestuff, in the 250mL Erlenmeyer flask, add distilled water 65mL and be configured to dye liquor.Erlenmeyer flask is put in the vibration dyeing machinery, behind 60 ℃ of insulation 5min, adds 200g/L Na 2SO4 25mL, continue to add 200g/LNa2CO3 10mL behind the insulation 5min, carry out suction filtration (during suction filtration after being incubated 30min again, pressure 0.075Mpa, the 5A qualitative filter paper), observe the filter paper residual condition.Reduce dye strength (G/L), no dyestuff is residual on filter paper, and the dye strength (G/L) of this moment is the salt tolerant alkali dissolution of dyestuff.
2, enhancing rate test: pure cotton fabric is pressed 60 ℃ of constant temperature technology dyeing of reactive dyestuffs, and dyeing concentration is 0.5%, 1%, 2%, 4%, 6%o.w.f (dyestuff is heavy to fabric).Dyeing back fabric is tested its Apparent Depth K/S value and record with the Datacolor color measurement instrument after fixed temperature and humidity is handled.
3, degree of fixation test: the dye liquor preparation, press 60 ℃ of constant temperature technology dyeing of reactive dyestuffs.After dyeing finishes, the cloth specimen in the B dye bath is carried out washing according to the following steps, and with 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 carried out soap boiling, the detergent that also adds same amount in the A dye bath carried out soap boiling.The A dye bath is soaped and is finished postcooling to room temperature, and constant volume is 500mL.A behind the 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).
The * 100% of degree of fixation=(1-XBMB/XAMA)
4, just dye the test of rate and degree of exhaustion: the dye liquor preparation, press 60 ℃ of constant temperature technology dyeing of reactive dyestuffs.Respectively before adding alkali and on dye and finish to take a sample before the soap boiling, measure the absorbance of dyeing residual liquid, with dye liquor absorbance before the dyeing relatively.
Just dye rate=(1-adds the absorbance of the preceding dye liquor of absorbance/dyeing of the preceding dye liquor of alkali) * 100%
Degree of exhaustion=(1-soap before the absorbance of the preceding dye liquor of absorbance/dyeing of dye liquor) * 100%
5, move the test of staining index MI value: two onesize A, B cloth specimen input are added with in the dye bath of dyestuff, sodium sulfate, behind 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 yellow soda ash fixation 60min behind dyeing (move and dye) 20min.The apparent dye yield (K/S) that compares B cloth specimen and C cloth specimen.
Move apparent dye yield (K/S) * 1000% of apparent dye yield (the K/S)/B cloth specimen of staining index MI=C cloth specimen
6, the water colour of anti-chlorination fastness 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: measure by Japanese standard JIS L0888.
Dye type shown in the according to the form below 1 and consumption thereof by ordinary method uniform mixing in this area, are prepared the various blue active dye compositions of the embodiment of the invention with various dye components.
" % " in the table 1 all represents weight %, is benchmark with the gross weight of dye composite.
Table 1
| Numbering | The reactive dyestuffs title | Form |
| 1 | A | 70% dyestuff I-2+30% dyestuff II-1 |
| 2 | B | 50% dyestuff I-2+50% dyestuff II-1 |
| 3 | C | 30% dyestuff I-2+70% dyestuff II-1 |
| 4 | D | 70% dyestuff I-1+30% dyestuff II-6 |
| 5 | E | 50% dyestuff I-1+50% dyestuff II-6 |
| 6 | F | 30% dyestuff I-1+70% dyestuff II-6 |
| 7 | Reference W | 100% dyestuff I-1 |
| 8 | Reference X | 100% dyestuff I-2 |
| 9 | Reference Y | 100% dyestuff II-1 |
| 10 | Reference Z | 100% dyestuff II-6 |
Embodiment 1
The coloured light of blue active dye composition of the present invention
The dyestuff color and luster of general formula (I) expression is royalblue, and the dyestuff color and luster of general formula (II) expression is the 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 constitute the three primary colors combination with other redness, yellow dyes effectively, improves its actual application value.
Embodiment 2
The test of salt tolerant alkali solubility
Measure the salt tolerant alkali solubility of following dyestuff as stated above, test result is recorded in the table 2
Table 2
By table 2 as seen:
Blue active dye composition of the present invention is compared with the dyestuff of general formula (I) expression, and its salt tolerant alkali solubility 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 610nm place)
Measure the enhancing rate of following dyestuff as stated above, test result is recorded in the table 3
Table 3
By table 3 as seen:
1) blue active dye composition of the present invention is compared with the dyestuff of general formula (I) expression, and its enhancing rate significantly improves, and has improved the shortcoming of general formula (I) expression dyestuff depth difference;
2) the enhancing rate measured value of 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
Measure the degree of fixation of following dyestuff as stated above, test result is recorded in the table 4
Table 4
By table 4 as seen:
The degree of fixation measured value of blue active dye composition of the present invention apparently higher than its weighted mean of forming dyestuff, has embodied the effect of compound synergic.
Embodiment 5
Just dying rate and degree of exhaustion measures
Measure the first rate and the degree of exhaustion of dying of following dyestuff as stated above, test result is recorded in the table 5
Table 5
By table 5 as seen:
1) the first rate of dying of blue active dye composition of the present invention is compared with dyestuff I-1 with degree of exhaustion, increases and improves, and shows and conventional three primary colors Huang, red good consistency when dying;
2) blue active dye composition of the present invention can significantly reduce dyestuff I and just dyes gap between rate and the degree of exhaustion, dyes the dyeing rate that adds dyestuff behind the alkali in the process on promptly reducing, and avoids dying the too fast look flower phenomenon that causes, and improves level-dyeing property;
3) the first rate and the degree of exhaustion measured value of dying of blue active dye composition of the present invention all is higher than the weighted mean that it forms dyestuff, illustrates that dye composite has better dyeing capacity, helps the set of dyestuff, improves dye utilization rate.
Embodiment 6
Moving staining index measures
Measure the staining index that moves of following dyestuff as stated above, test result is recorded in the table 6
Table 6
By table 6 as seen:
Blue active dye composition of the present invention is compared with the reactive dyestuffs of general formula (I) expression, still can keep higher migration property energy, has good level dyeing performance.
Embodiment 7
The water dungeon of anti-chlorination degree
Measure the water colour of anti-chlorination fastness of following dyestuff as stated above, test result is recorded in the table 7
Table 7
By table 7 as seen:
Blue active dye composition of the present invention has the good water dungeon of anti-chlorination degree, can effectively improve the problem of the dyestuff I-1 water dungeon of anti-chlorination degree difference.
Embodiment 8
Colour fastness to perspiration
Measure the colour fastness to perspiration of following dyestuff as stated above, test result is recorded in the table 8
Table 8
By table 8 as seen:
Blue active dye composition of the present invention has excellent colour fastness to perspiration.
Embodiment 9
Fastness to soaping, color fastness to water and color fastness to sea water
Measure fastness to soaping, color fastness to water and the color fastness to sea water of following dyestuff as stated above, test result is recorded in the table 9
Table 9
By table 9 as seen:
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
Sun-resistant fastness
Measure the sun-resistant fastness of following dyestuff as stated above, test result is recorded in the table 10
Table 10
By table 10 as seen:
Blue active dye composition of the present invention still keeps the characteristics of dyestuff I-1, has good sun-resistant fastness.
Embodiment 11
The photochromic fastness of sweat proof
Measure the photochromic fastness of sweat proof of following dyestuff as stated above, test result is recorded in the table 11
Table 11
By table 11 as seen:
Blue active dye composition of the present invention still keeps the characteristics of dyestuff I-2, has the photochromic fastness of good sweat proof.
By above embodiment, 2-11 can draw to draw a conclusion by table:
1), blue active dye composition of the present invention, significantly improved the shortcoming of general formula (I) expression dyestuff salt tolerant alkali solubility difference;
2), blue active dye composition of the present invention, compare with the dyestuff of general formula (I) expression, its enhancing rate significantly improves, and has improved the shortcoming of general formula (I) expression dyestuff depth difference;
3), blue active dye composition of the present invention, its degree of fixation measured value apparently higher than its weighted mean of forming dyestuff, has embodied the effect of compound synergic;
4), blue active dye composition of the present invention, it just dyes rate compares with the dyestuff of general formula (I) expression with degree of exhaustion, is significantly improved and improves, and shows with conventional three primary colors Huang, red is same when dying good consistency;
5), blue active dye composition of the present invention has that good moving dyed and the level dyeing performance;
6), blue active dye composition of the present invention, can effectively improve the problem of general formula (I) the expression dyestuff water dungeon of anti-chlorination degree difference;
7), 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), blue active dye composition of the present invention still keeps the advantage of general formula (I) expression dyestuff, has good sun-resistant fastness and the photochromic fastness of sweat proof.
Claims (10)
1. blue active dye composition, this dye composite comprise one or more be selected from below shown in the dye composition of general formula (1) expression and one or more be selected from below shown in the dye composition of general formula (2) expression:
General formula (1)
In the formula:
R
1Be H, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, sulfo group, carboxyl or halogen;
R
2Be H, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, sulfo group or halogen;
Y
1For-CH
2CH
2OSO
3M ,-CH=CH
2,-CH
2CH
2OH or-CH
2CH
2Cl;
M be H, Na, K or-NH
4Group;
General formula (2)
In the 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
R
3And R
4Be H, halogen, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or sulfo group;
R
5Be sulfonic group;
N is 0,1 or 2;
M is H, Na, K or NH
4Group.
2. the described blue active dye composition of claim 1, its characteristic are that the dye composition of general formula (1) expression is 80～20: 20～80 with the weight ratio of the dye composition that general formula (2) is represented.
3. the described blue active dye composition of claim 1, its characteristic be, in general formula (1) and the general formula (2),
R
1And R
2Be H, C independently respectively
1-C
4Alkoxyl group, sulfo group or carboxyl;
R
3And R
4Be H, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or sulfo group;
R
5Be sulfo group;
Y
1And Y
2Be independently-CH respectively
2CH
2OSO
3M or-CH=CH
2
N is 0 or 1;
M is H, Na, K or NH
4Group.
4. the described blue active dye composition of claim 1, its characteristic is, the R in the general formula (1)
1And R
2Group is separately located in respectively on the benzene nucleus-ortho position, a position or the contraposition of NH-group.In the general formula (1)-SO
2Y
1Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH-group.
5. the described blue active dye composition of claim 1, its characteristic is, the T group of general formula (2), be selected from-NHCOQ or-SO
2Y
2Group, T group be positioned on the benzene nucleus-contraposition or a position of N=N-group.
6. the described blue active dye composition of claim 1, its characteristic is, the R of general formula (2)
3And R
4Group is separately located in respectively on the benzene nucleus-ortho position, a position and the contraposition of N=N-group.
7. the described blue active dye composition of claim 1, its characteristic is, the R of general formula (2)
5Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of N=N-group.
8. the described blue active dye composition of claim 1, its characteristic be, general formula (2)-the NHCOQ group, be positioned on the benzene nucleus-ortho position, a position or the contraposition of N=N-group.
9. the described blue active dye composition of claim 1, its characteristic are that the dye composition of general formula (1) expression 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 of general formula (2) expression is:
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.
10. each described blue active dye composition in the claim 1～9, the application of woolen dyeing aspect.
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| CN200910247503.8A CN102115613B (en) | 2009-12-30 | 2009-12-30 | Blue reactive dye composition and dyeing application to fiber material thereof |
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|---|---|---|---|
| CN200910247503.8A CN102115613B (en) | 2009-12-30 | 2009-12-30 | Blue reactive dye composition and dyeing application to fiber material thereof |
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| CN102604411A (en) * | 2012-01-19 | 2012-07-25 | 上海雅运纺织化工股份有限公司 | Synthesis and dyeing application of anthraquinone type blue acid dye compound |
| CN102850823A (en) * | 2012-09-28 | 2013-01-02 | 浙江亿得化工有限公司 | Composite anthraquinone-type cobalt blue reactive dye |
| CN103571232A (en) * | 2013-11-07 | 2014-02-12 | 褚平忠 | Reactive brilliant blue KN-RSR dye composition for printing fabrics as well as preparation method of composition |
| CN104448927A (en) * | 2014-11-06 | 2015-03-25 | 浙江亿得化工有限公司 | Composite active blue dye |
| CN106349745A (en) * | 2016-08-25 | 2017-01-25 | 浙江劲光实业股份有限公司 | Activated azo dye and preparation method and application thereof |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102504593A (en) * | 2011-10-13 | 2012-06-20 | 上海雅运纺织化工股份有限公司 | Blue dye composition and use thereof for fiber dyeing |
| CN102604411A (en) * | 2012-01-19 | 2012-07-25 | 上海雅运纺织化工股份有限公司 | Synthesis and dyeing application of anthraquinone type blue acid dye compound |
| CN102604411B (en) * | 2012-01-19 | 2014-06-11 | 上海雅运纺织化工股份有限公司 | Synthesis and dyeing application of anthraquinone type blue acid dye compound |
| CN102850823A (en) * | 2012-09-28 | 2013-01-02 | 浙江亿得化工有限公司 | Composite anthraquinone-type cobalt blue reactive dye |
| CN103571232A (en) * | 2013-11-07 | 2014-02-12 | 褚平忠 | Reactive brilliant blue KN-RSR dye composition for printing fabrics as well as preparation method of composition |
| CN104448927A (en) * | 2014-11-06 | 2015-03-25 | 浙江亿得化工有限公司 | Composite active blue dye |
| CN106349745A (en) * | 2016-08-25 | 2017-01-25 | 浙江劲光实业股份有限公司 | Activated azo dye and preparation method and application thereof |
| 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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