CN101418138B - Navy blue reactive dyes composite for low salt dyeing and dyeing application thereof - Google Patents
Navy blue reactive dyes composite for low salt dyeing and dyeing application thereof Download PDFInfo
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- CN101418138B CN101418138B CN2007100473700A CN200710047370A CN101418138B CN 101418138 B CN101418138 B CN 101418138B CN 2007100473700 A CN2007100473700 A CN 2007100473700A CN 200710047370 A CN200710047370 A CN 200710047370A CN 101418138 B CN101418138 B CN 101418138B
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- 0 *c1cc(NC(C(C2C(c3c4cccc3)=O)C4=O)=CC(S(O)(=O)=O)=C2N)ccc1 Chemical compound *c1cc(NC(C(C2C(c3c4cccc3)=O)C4=O)=CC(S(O)(=O)=O)=C2N)ccc1 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention provides an atroceruleous reactive dye composition for hypohaline dyeing, which comprises one or a plurality of types of dye as shown by a general formula (1) and one or a multiple kinds of dye as shown by a general formula (2) which are mixed with each other in proportion. The atroceruleous reactive dye composition has bright and beautiful color and superior dyeing performance and dyeing fastness. People are pleasantly surprised by the fact that the amount of inorganic salt used under the condition of dyeing is only approximately one half of that of the prior art when the atroceruleous reactive dye composition is applied to hypohaline dyeing. The fixation rate, the lifting property and the leveling property of the reactive dye composition and the compatibility of the reactive dye composition when being dyed together with other commonly used red reactive dye and yellow reactive dye are obviously improved compared with the dye as shown in the formula (1).
Description
Technical field
The present invention relates to navy blue reactive dye composition that a kind of low salt dyeing uses and the tint applications on filamentary material thereof.
Background technology
Reactive dyestuffs with beautiful in colour, chromatogram is complete, application is easy, with low cost, fastness is good and celebrated.But in the cellulosic fibre traditional dyeing,, usually must add a large amount of inorganic salt (like sodium-chlor or sodium sulfate) and urge to dye for improving the dye uptake and the degree of fixation of reactive dyestuffs.Different according to the breed structure of reactive dyestuffs and color and luster are shortly dyed used traditional technology and are generally 30～120g/L with the salt amount.Although the processing to organic cpds in the dyeing waste water obtains remarkable progress at present, the dyeing waste water of supersalinity is difficult to handle through simple materialization and biochemical method.
Therefore, the environmental pollution problem of active dye printing waste water receives people's serious concern day by day.
C.I. Reactive Blue 19 100 # is that well-known anthraquinone is the dark blue reactive dye kind.This dyestuff becomes clear with lovely luster and good light fastness and sweat proof light fastness is good at.But defective is that its fastness to chlorine, level-dyeing property and solubleness are unsatisfactory, is difficult to excellent consistency again and dyes together with Huang, red reactive dyes commonly used, thereby be difficult to satisfy the demand of current printing and dyeing, limits its widespread use.
In recent years, in this area C.I. Reactive Blue 19 100 # compsn or mixture have been done extensive studies.The patented claim relevant with the present invention has following seven pieces:
1.CN 1580132 (2005) (Hua Bachang is dyed in Shanghai)
2.WO 2005/090485 (Ciba Specialty Chemicals Holding Inc)
3.CN 1934195 (2007) (Huntsman Advanced Materials Sw)
4.JP 2006-28350 (SUMITOMO CHEMICAL company)
5.JP 7207180 (1995) (Mitsubishi changes into company)
6.JP 8048903 (1996) (Mitsubishi changes into company)
7.EP 905201 (1999) (Bezema companies)
In these patents or the patented claim; Use C.I. Reactive Blue 222 and verivate thereof, C.I. REACTIVE BLACK 5 100 and verivate thereof, C.I. Reactive Blue 221 and verivate thereof and dark blue reactive dye (dyestuff III) respectively; # carries out modification to the C.I. Reactive Blue 19 100; To improve or to improve some defective on its dyeing behavior, for example improve and improve its level-dyeing property, enhancing and degree of fixation etc.
(dyestuff III)
Comprehensive dyeing behavior of the navy blue reactive dye composition of above-mentioned patent or patented claim still remains further to improve and improve.
The inventor is through great deal of experimental, and surprised discovery contains one or more dark blue reactive dyes of following general formula (2) expression and the dye composite of one or more dark blue reactive dyes that general formula (1) is represented has good dyeing behavior and each item dyefastness.Particularly pleasantly surprised is that this dye composite has excellent low salt dyeing performance.
For this reason, the present invention success a kind of low salt dyeing usefulness is provided, and have the navy blue reactive dye composition of good dyeing behavior and each item dyefastness.
Summary of the invention
One of the object of the invention provides a kind of one or more dark blue reactive dyes of general formula (2) expression and dye composite of one or more dark blue reactive dyes that general formula (1) is represented of containing, and it has very excellent dyeing behavior and each item fastness.
Particularly pleasantly surprised is that this dye composite has excellent low salt dyeing performance.
Meanwhile, this dye composite is compared with one or more dark blue reactive dyes of general formula (1) expression, and its degree of fixation and lifting rate obviously improve.Particularly importantly, this dye composite has and other red, excellent compatibility that Yellow active dye dyes altogether commonly used.
Navy dye composite provided by the invention comprise the certain proportion blended one or more be selected from below shown in general formula
The dyestuff of general formula (2) expression shown in below (1) dyestuff of expression is selected from one or more:
General formula (1)
In the formula: Y
1Be selected from-CH
2CH
2OSO
3M and-CH=CH
2
M is selected from H and basic metal;
R
1Be selected from H, C
1～C
4Alkyl, C
1～C
4Alkoxyl group and carboxyl.
General formula (2)
In the formula: X
1And X
2Be selected from Cl, F and OH;
M is selected from H and basic metal;
R
2And R
3Be selected from H, CH
3And C
2H
5
Y
2Be selected from-CH
2CH
2OSO
3M ,-CH
2CH
2OH and-CH=CH
2
R
4Be selected from-CN ,-CH
2CH
2OH with
In the following formula: R
5Be selected from-SO
3M and H;
R
6Be selected from-H ,-CH
3,-Cl and-SO
2Y
3
Y
3Be selected from-H ,-CH
2CH
2OSO
3M ,-CH
2CH
2OH and-CH=CH
2
The present invention also provides above-mentioned navy blue reactive dye composition containing carbonyl and/or formamido-material, particularly the application in the filamentary material dyeing.
Navy blue reactive dye composition of the present invention has excellent dyeing behavior and each item dyefastness, and with the consistency of other red, excellence of using always that Yellow active dye dyes altogether.
Embodiment
Comprise the dyestuff of one or more general formulas (1) expression and the dyestuff of one or more general formulas (2) expression in the dye composite of the present invention.
In dye composite of the present invention, the dyestuff of general formula (1) expression (being called for short dyestuff I) is 90～40: 10～60 with the weight ratio of the dyestuff (being called for short dyestuff II) of general formula (2) expression, 80～50: 20～50, preferably 70～60: 30～40.
One preferred embodiment in, in the general formula (1)-SO
2Y
1Group is positioned on the benzene nucleus-the NH-group between position or contraposition, R
1Group is positioned on the benzene nucleus-ortho position of NH-group.
Another preferred embodiment in, in the general formula (2)-SO
2Y
2Group is positioned on the benzene nucleus-the NH-group between position or contraposition.
Another preferred embodiment in, the R in the general formula (2)
4Group is selected from
Group, then R
5Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH-group; R
6Group is positioned on the benzene nucleus-contraposition or a position of NH-group.
Among the present invention, the dyestuff of general formula (1) expression for example comprises following instance:
(dyestuff I-1)
(dyestuff I-2)
(dyestuff I-3)
(dyestuff I-4)
(dyestuff I-5)
The dyestuff example of formula of of the present invention (2) expression comprises following instance:
(dyestuff II-1)
(dyestuff II-2)
(dyestuff II-3)
(dyestuff II-4)
(dyestuff II-5)
(dyestuff II-6)
The reactive dyestuffs of general formula (1) and general formula (2) expression are known dye.
The reactive dyestuffs of general formula (1) expression are well-known C.I. Reactive Blue 19 100, and many documents disclose the structure and the compound method thereof of these reactive dyestuffs, and for example CN 1034012 (1989).
JP 2001-2952, JP 2001-200175, JP 2001-214086, JP 2001-207076, JP 2001-335718, JP 2001-329187, JP 2001-323181, JP 2002-20646 disclose the structure and the compound method thereof of the dyestuff of general formula (2) expression respectively.
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 by actual needs, does not have special qualification, generally is no more than 20 weight %.Inorganic salts for example is like NaCl, Na
2SO
4, content 0-10 weight %, dispersant 0-10 weight %, the pH regulator agent, like SODIUM PHOSPHATE, MONOBASIC or Sodium phosphate, dibasic, content 0-5 weight %, dust-proofing agent 0-10 weight %, solubility promoter 1-15 weight %.The present composition also can be made up of general formula (1) dyestuff and general formula (2) dyestuff of above-mentioned weight ratio basically.
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 is mixed by the weight ratio of regulation.Mix available various ordinary method, like 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.
Navy blue reactive dye composition of the present invention is suitable for dyeing and various widely material thereof; The material that particularly contains carboxyl and/or formamido-; Be more especially filamentary material, 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 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.
Each item testing method of embodiment
Each item performance of following embodiment is tested by following each item testing method:
1. soaping fastness: measure by international standard ISO 105 C03.
2. fastness to chlorine: measure by international standard ISO 105 E03.
3. light fastness: measure by international standard ISO 105 B02.
4. dye uptake: prepare two parts of identical dye baths, be respectively A, B.Do not put cloth specimen in the A dye bath.A, B two dye baths are dyeed by the standard dyeing.After dyeing finishes, draw A, B dyeing residual liquid 10mL, constant volume is 500mL respectively.A behind the constant volume, B dyeing residual liquid are diluted to certain multiple M
A, M
B, test the absorptance values X of its diluent when maximum absorption wavelength
A, X
B(X
A, X
BShould be between 0.2-0.7.)
5. lifting rate: press dye dosage 0.5%, 1%, 2%, 4%, 6%, 8%, 10% preparation dye liquor respectively, dye by the standard dyeing.Cloth specimen after soaping, dry after the dyeing is surveyed its K/S value on the color measurement and color match appearance, make the trend map of K/S value-dye dosage, be the lifting rate curve of reactive dyestuffs.
6. the dyeing of different inorganic salt consumptions
7. press inorganic salt consumption 10g/L, 30g/L, 50g/L respectively and prepare dye liquor, dye by the standard dyeing.Cloth specimen after soaping, dry after the dyeing is surveyed its K/S value on the color measurement and color match appearance, make the trend map of K/S value-dye dosage, be the dyeing of the different inorganic salt consumptions of reactive dyestuffs.
The employed dye composite of embodiment
Employed dye composite and reference reactive dye compositions and homogencous dyes are listed in table 1 in the embodiment of the invention.
Comprise following content:
1. the different ratios compsn of dark blue reactive dye of the present invention;
2. the navy blue reactive dye composition of other known patent or mixture;
Be C.I. Reactive Blue 19 100 #+ dyestuff III
C.I. Reactive Blue 19 100 #+ dyestuff IV
(dyestuff III)
(dyestuff IV)
3.C.I. Reactive Blue 19 100 #
Table 1
| Numbering | The reactive dyestuffs title | Form |
| 12345 references, 1 reference, 2 references, 3 references, 4 references, 5 references 6 | ?A?B?C?D?E?W?X?Y?Z?U?V | 70% dyestuff I-1+30% dyestuff II-1,70% dyestuff I-1+30% dyestuff II-2,80% dyestuff I-4+20% dyestuff II-1,60% dyestuff I-1+10% dyestuff I-3+30% dyestuff II-1,50% dyestuff I-1+50% dyestuff II-1,70% dyestuff I-1+30% dyestuff III, 70% dyestuff I-1+30% dyestuff IV, 50% dyestuff I-1+50% dyestuff III, 50% dyestuff I-1+50% dyestuff IV, 100% dyestuff I-1,100% dyestuff II-1 |
Embodiment 1
The stain test of different inorganic salt consumptions
When dye uptake is different time points fabric on the amount of dying dye yield (testing apparatus: computer color measurement and color match appearance; Model: QuestXE; Producer: HunterLab) account for the weight percent of used dyestuff.Therefore, when dyeing, each time point of dyestuff colouring is measured and is calculated first dye uptake S value, final dye uptake E value and its result of degree of fixation F value respectively and is shown in table 2～4 respectively.
1. reactive dye compositions of the present invention (dyestuff A)
Table 2
Dye level: 3%o.w.f.
| The sodium sulfate consumption | The S value | The E value | The F value |
| 50g/L | 47.8％ | 94.5％ | 78.7％ |
| 30g/L | 42.7％ | 91.6％ | 73.8％ |
| 10g/L | 33.0％ | 85.0％ | 68.0％ |
2. reference reactive dye compositions (dyestuff W)
Table 3
Dye level: 3%o.w.f.
| The sodium sulfate consumption | The S value | The E value | The F value |
| 50g/L | 32.1％ | 87.1％ | 71.4％ |
| 30g/L | 23.9％ | 82.1％ | 67.2％ |
| 10g/L | 14.9％ | 72.8％ | 57.3％ |
3. reference reactive dye compositions (dyestuff X)
Table 4
Dye level: 3%o.w.f.
| The sodium sulfate consumption | The S value | The E value | The F value |
| 50g/L | 40.0％ | 90.8％ | 74.1％ |
| 30g/L | 31.4％ | 86.3％ | 68.0％ |
| 10g/L | 20.4％ | 77.2％ | 60.1％ |
Data by table 2～4 are visible, and reactive dyeing reaches same S value, E value, F value, and the inorganic salt consumption of reactive dye compositions dyestuff A of the present invention can lack 20g/L than dyestuff W, dyestuff X, has significantly reduced the pollution to environment like this.
Embodiment 2
The stain test of different inorganic salt consumptions
1. reactive dye compositions of the present invention (dyestuff E)
Table 5
Dye level: 3%o.w.f.
| The sodium sulfate consumption | The S value | The E value | The F value |
| 50g/L | 44.4％ | 91.2％ | 75.6％ |
| 30g/L | 39.1％ | 89.0％ | 70.2％ |
| 10g/L | 30.3％ | 82.1％ | 65.3％ |
2. reference reactive dye compositions (dyestuff Y)
Table 6
Dye level: 3%o.w.f.
| The sodium sulfate consumption | The S value | The E value | The F value |
| 50g/L | 37.1％ | 84.5％ | 68.0％ |
| 30g/L | 20.2％ | 79.3％ | 64.4％ |
| 10g/L | 18.4％ | 69.2％ | 54.4％ |
3. reference reactive dye compositions (dyestuff Z)
Table 7
Dye level: 3%o.w.f.
| The sodium sulfate consumption | The S value | The E value | The F value |
| 50g/L | 36.8％ | 87.3％ | 71.0％ |
| 30g/L | 28.4％ | 83.1％ | 64.8％ |
| 10g/L | 17.8％ | 74.2％ | 57.3％ |
Data by table 2～4 are visible, and reactive dyeing reaches same S value, E value, F value, and the inorganic salt consumption of reactive dye compositions dyestuff E of the present invention can lack 20g/L than dyestuff Y, dyestuff Z, has significantly reduced the pollution to environment like this.
Embodiment 3
Compatibility test
Test navy blue reactive dye composition of the present invention and its composition dyestuff as stated above respectively, and C.I. REACTIVE Yellow 145 #, C.I. REACTIVE Red 195 # on dye curve.Its data are listed in table 8
Table 8
Dye curve on dark blue reactive dye of the present invention and C.I. REACTIVE Yellow 145 and the C.I. REACTIVE Red 195
(dyestuff 2%o.w.f., sodium sulfate 40g/L, yellow soda ash 20g/L)
| Dyeing time | Dye uptake % | |||||||
| 10’ | 30’ | 32’ | 35’ | 40’ | 50’ | 70’ | 90’ | |
| C.I. REACTIVE Yellow 145 C.I. REACTIVE Red 195 reference U reference V dyestuff A | 46.5 43.8 29.3 30.7 48.81 | 53.5 48.6 39.2 43.6 53.85 | 67.0 59.9 59.8 65.2 74.49 | 74.0 64.8 72.7 67.8 78.68 | 79.8 72.5 80.8 77.0 85.22 | 84.2 79.6 89.3 84.3 91.66 | 88.0 82.1 92.1 88.2 93.87 | 89.0 82.7 92.4 91.7 93.90 |
| Dyestuff B | 44.85 | 51.13 | 68.68 | 74.36 | 75.29 | 80.91 | 91.92 | 93.94 |
Can find out that by above data dark blue reactive dye of the present invention has very good consistency with Yellow active dye (C.I. REACTIVE Yellow 145) and red reactive dyes (C.I. REACTIVE Red 195) commonly used.
Embodiment 4
The test of lifting rate
Test the lifting rate of navy blue reactive dye composition of the present invention as stated above respectively, # compares with the C.I. Reactive Blue 19 100, and its lifting rate improves a lot.Data are listed in table 9.
Table 9
| The dyestuff title | 1% lifting rate (%) | 2% lifting rate (%) | 4% lifting rate (%) | 6% lifting rate (%) |
| Dyestuff A dyestuff B dyestuff U (reference) | 147.63 142.06 100* | 150 150.00 100* | 150.08 144.63 100* | 143.96 133.44 100* |
U is 100 with the reference dyestuff, lists relative value.
Embodiment 5
The test of each item dyefastness
Each item dyefastness of dyestuff A of the present invention and dyestuff B, following through its data of test:
Dyestuff A: 4 grades of washing fastness 4-5 levels, light fastness 4-5 level, sweat light fastness (sour sweat) 4-5 level, sweat light fastness (alkali sweat)
Dyestuff B: 4 grades of washing fastness 4-5 levels, 4 grades of light fastnesss, sweat light fastness (sour sweat) 4-5 level, sweat light fastness (alkali sweat)
Claims (10)
1. the dyestuff of general formula (2) expression shown in below the dyestuff of general formula (1) expression shown in below navy blue reactive dye composition, this dye composite are selected from by one or more is selected from one or more is formed,
General formula (1)
In the formula: Y
1Be selected from-CH
2CH
2OSO
3M and-CH=CH
2
M is selected from H and basic metal;
R
1Be selected from H, C
1～C
4Alkyl, C
1～C
4Alkoxyl group and carboxyl;
General formula (2)
In the formula: X
1And X
2Be selected from Cl, F and OH;
M is selected from H and basic metal;
R
2And R
3Be selected from H, CH
3And C
2H
5
Y
2Be selected from-CH
2CH
2OSO
3M ,-CH
2CH
2OH and-CH=CH
2
R
4Be selected from-CN ,-CH
2CH
2OH with
In the following formula: R
5Be selected from-SO
3M and H;
R
6Be selected from-H ,-CH
3,-Cl and-SO
2Y
3
Y
3Be selected from-H ,-CH
2CH
2OSO
3M ,-CH
2CH
2OH and-CH=CH
2
Wherein, the weight ratio of one or more dyestuffs of one or more dyestuffs of general formula (1) expression and general formula (2) expression is general formula (a 1) dyestuff: general formula (2) dyestuff=90～40: 10～60.
2. the described navy blue reactive dye composition of claim 1, its characteristic are that one or more dyestuffs of general formula (1) expression are general formula (1) dyestuff with the weight ratio of one or more dyestuffs that general formula (2) is represented: general formula (2) dyestuff=80～50: 20～50.
3. the described navy blue reactive dye composition of claim 1, its characteristic be, in the general formula (1)-and SO
2Y
1Group is positioned on the benzene nucleus-the NH-group between position or contraposition, R
1Group is positioned on the benzene nucleus-ortho position of NH-group.
4. the described navy blue reactive dye composition of claim 3, its characteristic is that general formula (1) is selected from following dyestuff:
(dyestuff I-1)
(dyestuff I-2)
(dyestuff I-3)
(dyestuff I-4)
(dyestuff I-5)
5. the described navy blue reactive dye composition of claim 1, its characteristic be, in the general formula (2)-and SO
2Y
2Group is positioned on the benzene nucleus-the NH-group between position or contraposition.
6. the described navy blue reactive dye composition of claim 1, its characteristic are, R in the general formula (2)
5Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH-group; R
6Group is positioned on the benzene nucleus-contraposition or a position of NH-group.
7. claim 1,5 or 6 described navy blue reactive dye compositions, its characteristic is that general formula (2) is selected from:
(dyestuff II-1)
(dyestuff II-2)
(dyestuff II-3)
(dyestuff II-4)
(dyestuff II-5)
(dyestuff II-6).
8. the described navy blue reactive dye composition of claim 1, its characteristic is that M is selected from H, Na and K.
Among the claim 1-8 each described navy blue reactive dye composition in the tint applications that contains on carbonyl and/or the formamido-material.
10. the described application of claim 9, wherein containing carbonyl and/or formamido-material is to contain carbonyl and/or formamido-filamentary material.
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|---|---|---|---|
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|---|---|---|---|
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| CN101418138B true CN101418138B (en) | 2012-05-09 |
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| CN102329522B (en) * | 2011-09-29 | 2016-08-03 | 天津德凯化工股份有限公司 | A kind of reactive dye and preparation method thereof |
| CN102433026A (en) * | 2011-09-29 | 2012-05-02 | 天津德凯化工股份有限公司 | Black active dye for pure cotton or cotton and wool blended textile dyeing and preparation method thereof |
| 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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006022447A (en) * | 2004-07-09 | 2006-01-26 | Sumitomo Chemical Co Ltd | Method for dyeing soybean protein-containing fiber |
| JP2006052249A (en) * | 2004-08-10 | 2006-02-23 | Sumitomo Chemical Co Ltd | Reactive dyestuff composition and method of dyeing |
| CN101023141A (en) * | 2004-11-19 | 2007-08-22 | 德意志戴斯达纺织品及染料两合公司 | Reactive dyes |
-
2007
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006022447A (en) * | 2004-07-09 | 2006-01-26 | Sumitomo Chemical Co Ltd | Method for dyeing soybean protein-containing fiber |
| JP2006052249A (en) * | 2004-08-10 | 2006-02-23 | Sumitomo Chemical Co Ltd | Reactive dyestuff composition and method of dyeing |
| CN101023141A (en) * | 2004-11-19 | 2007-08-22 | 德意志戴斯达纺织品及染料两合公司 | Reactive dyes |
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