CN101323710B - Red reactive dye composition and dyeing application thereof - Google Patents
Red reactive dye composition and dyeing application thereof Download PDFInfo
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- CN101323710B CN101323710B CN2007100418313A CN200710041831A CN101323710B CN 101323710 B CN101323710 B CN 101323710B CN 2007100418313 A CN2007100418313 A CN 2007100418313A CN 200710041831 A CN200710041831 A CN 200710041831A CN 101323710 B CN101323710 B CN 101323710B
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Abstract
The invention provides a red reactive dye composition and a dying application thereof on fibre materials. The red reactive dye composition comprises one or more dyes with a general formula (1) and dyes with a general formula (2) and non-necessary dyes with a general formula (3), which are mixed in certain proportion. The red reactive dye composition has bright color and excellent dying fastness in various aspects; particularly, compared with other composition dyes, the thermal sensitivity resistance of the composition is significantly improved and enhanced.
Description
Technical field
The present invention relates to a kind of red reactive dye composition and the tint applications on filamentary material thereof.
Background technology
Excellent reactive dyestuffs should have very excellent application performance energy.
The exploitation of red reactive dyes is the focus of current concern always.
Red reactive dyes not only requires beautiful in colour bright, and can compatibleness preferably be arranged reactive dyestuffs effective and other color and luster.Red reactive dyes dyeing must possess good degree of fixation, enhancing and every fastness, and wherein light fastness, heat-resisting quick performance etc. are particularly important.
Printing and dyeing are produced in the drying course, and the thermo-responsive performance of dyestuff makes DYED FABRICS meet thermo-color, causes the difficulty of checking colors, and is the problem that the colourist makes great efforts to seek solution always.
WO-A-00/06652 disclose a series of with j acid be the color and luster of starting raw material by orange to blue disazo dyes, comprising the orchil of following general formula (1) expression.This orchil not only can reach excellent every application fastness, and has excellent compatibility.Yet this orchil has tangible thermal discoloration.
WO2005/040285 or CN1871308A disclose the dyestuff and the mixture of other dyestuff of following general formula (1) expression, comprising the orchil of representing with following general formula (3).The purpose of this patent is to improve the light firmness and the wet firmness of red reactive dyes, but does not relate to the heat-resisting quick performance of these orchils.In fact, meet with the painted fabric of this mixture and tangible look still to take place when hot become, have a strong impact on the processing and the outward appearance of fabric.
JP2002226724 (Sumitomo) has recorded and narrated the similar orchil that following general formula 2 is explained, but this manufacturing cost height, and also have very significantly thermal discoloration.
Summary of the invention
The inventor is surprisingly found out that, the dyestuff of general formula (1) expression shown in below one or more are selected from and following shown in the dyestuff of general formula (3) expression mix by a certain percentage with the dyestuff that the general formula (2) shown in following is represented, not only can reach excellent every application fastness, and excellent compatibility, and can also significantly improve heat-resisting quick performance.The dyestuff of general formula (3) expression shown in below adding in above-mentioned dye mixture can further improve heat-resisting quick performance.
Purpose of the present invention is to develop a kind of red reactive dye composition, has good heat-resisting quick performance, keeps excellent every application fastness simultaneously.
Through overtesting, the present invention has reached above-mentioned purpose.
The invention provides a kind of red reactive dye composition of tint applications excellent property, this dye composite comprise one or more be selected from below shown in general formula (1) expression dyestuff (hereafter dyestuff I), one or more be selected from below shown in the dyestuff (hereafter dyestuff II) of general formula (2) expression and one or more be selected from below shown in the dyestuff (hereafter dyestuff III) of general formula (3) expression.
The weight ratio of the dyestuff of the dyestuff of the dyestuff of general formula (1) expression and general formula (2) expression and general formula (3) expression is 30～90:5～25:0～50, is preferably 35～80:10～20:10～45,
In the general formula (1): X be selected from H ,-CH
2SO
3M and-CH
2COOM;
Y is selected from-CH
2CH
2OSO
3M and-CH=CH
2
R
1, R
2, R
3And R
4Be independently selected from H, C respectively
1-3Alkyl, C
1-3Alkoxyl group and-SO
3M, be preferably selected from H ,-CH
3,-OCH
3With-SO
3M;
M is selected from H or basic metal, as sodium, potassium.
In the general formula (2): X be selected from H ,-CH
2SO
3M and-CH
2COOM;
Y is selected from-CH
2CH
2OSO
3M and-CH=CH
2
R
5, R
6, R
7And R
8Be independently selected from H, C respectively
1-3Alkyl, C
1-3Alkoxyl group and-SO
3M, be preferably selected from H ,-CH
3,-OCH
3With-SO
3M;
M is selected from H or basic metal, as sodium, potassium.
In the general formula (3): X
1Be selected from Cl, F;
Y is selected from-CH
2CH
2OSO
3M and-CH=CH
2
Y
1Be selected from-CH
2CH
2OSO
3M and-CH=CH
2
R
9Be selected from C
1-3Alkyl, C
1-3Alkoxyl group and-SO
3M is preferably selected from-CH
3,-OCH
3With-SO
3M;
A is selected from 0,1;
B is selected from 0,1 and 2.
The inventor is surprised to find by experimental study, adopts dyestuff I, dyestuff II and non-essential dyestuff III to piece together the red reactive dye composition that mixes, and has the good application performance that it forms dyestuff concurrently, has given play to the synergistic effect of marked improvement.Simultaneously, improve its heat-resisting quick performance effectively.Reactive dye compositions of the present invention can be dyed filamentary material fastness excellence, heat-resisting quick well behaved red tone.
The present invention also provides above-mentioned red reactive dye composition to be applied to contain dyeing on carboxyl and/or the formamido-material, particularly filamentary material.
Embodiment
X in the general formula (1) is H, R
1, R
2, R
3, R
4Be independently selected from respectively H ,-CH
3,-OCH
3With-SO
3M, R
1And R
2Lay respectively at-ortho position or a position of N=N-group R
3And R
4Lay respectively at-ortho position or a position of N=N-group, M is hydrogen, sodium or potassium, two-SO in the general formula (1)
2Y group lays respectively at-contraposition or a position of N=N-group.
X in the general formula (2) is H, R
5, R
6, R
7, R
8Be independently selected from respectively H ,-CH
3,-OCH
3With-SO
3M, R
5And R
6Lay respectively at-ortho position or a position of N=N-group R
7And R
8Lay respectively at-ortho position or a position of N=N-group, M is hydrogen, sodium or potassium, two-SO
2Y group lays respectively at-ortho position or a position of N=N-group.
X in the general formula (3)
1Be Cl, R
9Be selected from-CH
3,-OCH
3With-SO
3M, R
9The b of group is selected from 0,1 and 2 respectively; R
9Group is separately located in respectively on the benzene nucleus-ortho position or the contraposition of N=N-group, or be positioned on the benzene nucleus 1 and 5, M is hydrogen, sodium or potassium.
In the general formula (3)-SO
2Y group is positioned at-ortho position or a position of NH-group;-SO
2Y
1Respectively independently or be positioned on the benzene nucleus-ortho position or the contraposition of N=N-group, or be positioned on the benzene nucleus 1 or 5, wherein a is selected from 0 and 1 respectively.
Dyestuff I, dyestuff II that the present invention is used and the example of dyestuff III include the compound of following structure:
Dyestuff Ia
Dyestuff Ib
Dyestuff Ic
Dyestuff IIa
Dyestuff IIb
Dyestuff IIc
Dyestuff IIIa
Dyestuff IIIb.
As mentioned above, dye composition Ia-Ic, dyestuff IIa-c, dyestuff IIIa-b are known dye, for example are disclosed among WO-A-00/06652, US 4,341,699 and the KoKai JP50-000178 (Sumitomo).Above-mentioned patent or patent application are with reference to being incorporated among the application.
Red reactive dye composition of the present invention also can contain the coloration 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 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 the dyestuff I of above-mentioned weight ratio with dyestuff II forms or be made up of dyestuff I, dyestuff II and the dyestuff III of above-mentioned weight ratio.
The preparation method of red reactive dye composition of the present invention comprises above-mentioned dyestuff I: dyestuff II: dyestuff III weight ratio is in accordance with regulations mixed.Mix available various ordinary method, as the mechanically mixing method.During mixing, dyestuff I, dyestuff II and dyestuff III 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.
Red reactive dye composition of the present invention is suitable for the various extremely widely materials of dyeing, particularly contains the material of carboxyl and/or formamido-, more especially filamentary material.These filamentary materials for example are native cellulose fibres, 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 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
Following the invention will be further described with reference to each embodiment, but should be appreciated that following embodiment only is exemplary, can not be used to limit protection scope of the present invention.
Parameters in following examples is measured as follows:
1) dyefastness: measure by international standard ISO 105 CO3.
2) heat-resisting quick performance: on same DYED FABRICS, cut size and be 6X10cm
2Two fabrics of I, II, fabric II lain in the baking oven dries.Simultaneously fabric I, II being tested aberration on color measurement and color match instrument Datacolor 400TM, is standard specimen with fabric I, the variable color situation of test fabric II, and DE* represents total color difference between the two, the big more expression difference of numerical value is big more.With the heat-resisting quick performance of fabric of judging this type of dyeing.
3) crock fastness: measure by international standard ISO 105 X12.
Embodiment 1
The exhaust dyeing of red reactive dye composition of the present invention.
Taking by weighing with respect to fiber is that the red reactive dye composition of 1% weight is fully in the being dissolved in barrel water.Under 1: 10 bath raio condition, cellulosic fabric (the all-cotton knitting cloth of Shanghai topic bridge yarn dyeing company limited) is kept circulation in overflow, in 10 minutes, add dye liquor, keep 35 ℃ of temperature, add 30 grams per liter sodium sulfate after 10 minutes, be warming up to 60 ℃, add 20 grams per liter soda ash, be incubated 45 minutes, wash then, soap, wash, dry at last.
Be used for above-mentioned dip-dye red reactive dye composition consist of dyestuff Ib: dyestuff IIc=80: 20 weight ratios.
Testing data shows that red reactive dye composition of the present invention shows good dye fastness and dye.DYED FABRICS is bright-coloured azarin color and luster.
3 grades of its washing fastness staining 4-5 levels, dry fastness 4-5 level, fastness to wet rubbing.By the heat-resisting quick performance of above-mentioned method mensuration gained fabric, the results are shown in Table 1.
Embodiment 2
Consist of dyestuff Ia except used red reactive dye composition: dyestuff IIa: dyestuff IIIb=50: 10: 40 weight ratios, operate by the method identical with embodiment 1.
Testing data shows that red reactive dye composition of the present invention shows good dye fastness and dye.DYED FABRICS is bright-coloured azarin color and luster.
3 grades of its washing fastness staining 4-5 levels, dry fastness 4-5 level, fastness to wet rubbing.By the heat-resisting quick performance of above-mentioned method mensuration gained fabric, the results are shown in Table 1.
Embodiment 3
Consist of dyestuff Ib except used red reactive dye composition: dyestuff IIb: dyestuff IIIa=50: 10: 40 weight ratios, operate by the method identical with embodiment 1.
Testing data shows that red reactive dye composition of the present invention shows good dye fastness and dye.DYED FABRICS is bright-coloured azarin color and luster.
3 grades of its washing fastness staining 4-5 levels, dry fastness 4-5 level, fastness to wet rubbing.By the heat-resisting quick performance of above-mentioned method mensuration gained fabric, the results are shown in Table 1.
Comparative Examples 1-8
Except independent use red reactive dyes Ia, dyestuff Ib, dyestuff Ic, dyestuff IIa, dyestuff IIb, dyestuff IIc, dyestuff IIIa and dyestuff IIIb, operate by dye dosage and the dyeing process identical with embodiment 1.
Testing data shows that red reactive dye composition of the present invention shows good dye fastness and dye.DYED FABRICS is bright-coloured azarin color and luster.
By the heat-resisting quick performance of above-mentioned method mensuration gained fabric, the results are shown in Table 1.
Embodiment 4
The pad dyeing dyeing of red reactive dye composition of the present invention.
Take by weighing by the red reactive dye composition of 10 grams per liter consumptions fully in the being dissolved in barrel water.Put into the groove of continuous dyeing machine with changing good dye liquor, after padding dye liquor, fabric (the cotton khaki that Jiangyin becomes roc printing and dyeing company limited to provide) dries, in the padding liquid that contains 30 grams per liter soda ash, 250 grams per liter sodium sulfate, pad then, decatize is 1 minute in 100 ℃ of saturation steams, washing, oven dry.
Be used for above-mentioned pad dyeing red reactive dye composition consist of dyestuff Ib: dyestuff IIc=80: 20 weight ratios.
Testing data shows that red reactive dye composition of the present invention shows good dye fastness and dye.DYED FABRICS is bright-coloured azarin color and luster.
3 grades of its washing fastness staining 4-5 levels, dry fastness 4-5 level, fastness to wet rubbing.By the heat-resisting quick performance of above-mentioned method mensuration gained fabric, the results are shown in Table 1.
Embodiment 5
Consist of dyestuff Ia except used red reactive dye composition: dyestuff IIa: dyestuff IIIb=35: 20: 45 weight ratios, operate by the method identical with embodiment 4.
Testing data shows that red reactive dye composition of the present invention shows good dye fastness and dye.DYED FABRICS is bright-coloured azarin color and luster.
3 grades of its washing fastness staining 4-5 levels, dry fastness 4-5 level, fastness to wet rubbing.By the heat-resisting quick performance of above-mentioned method mensuration gained fabric, the results are shown in Table 1.
Embodiment 6
Consist of dyestuff Ib except used red reactive dye composition: dyestuff IIb: dyestuff IIIa=35: 20: 45 weight ratios, operate by the method identical with embodiment 3.
Testing data shows that red reactive dye composition of the present invention shows good dye fastness and dye.DYED FABRICS is bright-coloured azarin color and luster.
3 grades of its washing fastness staining 4-5 levels, dry fastness 4-5 level, fastness to wet rubbing.By the heat-resisting quick performance of above-mentioned method mensuration gained fabric, the results are shown in Table 1.
Table 1
This shows that the anti-thermo-sensitivity of red reactive dye composition of the present invention significantly is better than the anti-thermo-sensitivity of various dye components, a difficult problem that makes DYED FABRICS meet this puzzlement printing and dyeing circle of thermo-color is greatly improved.
Claims (11)
1. red reactive dye composition, this dye composite comprise one or more be selected from below shown in general formula (1) expression dyestuff, one or more be selected from below shown in the dyestuff of general formula (2) expression and one or more be selected from below shown in the dyestuff of general formula (3) expression, the weight ratio of the dyestuff of the dyestuff of the dyestuff of general formula (1) expression, general formula (2) expression and general formula (3) expression is 30～90: 5～25: 0～50
In the general formula (1): X is H;
Y is selected from-CH
2CH
2OSO
3M and-CH=CH
2
R
1, R
2, R
3And R
4Be independently selected from H, C respectively
1-3Alkyl, C
1-3Alkoxyl group and-SO
3M;
M is selected from H and basic metal,
In the general formula (2): X is H;
Y is selected from-CH
2CH
2OSO
3M and-CH=CH
2
R
5, R
6, R
7And R
8Be independently selected from H, C respectively
1-3Alkyl, C
1-3Alkoxyl group and-SO
3M;
M is selected from H and basic metal,
[general formula (3)]
In the general formula (3): X
1Be selected from Cl and F;
Y is selected from-CH
2CH
2OSO
3M and-CH=CH
2
Y
1Be selected from-CH
2CH
2OSO
3M and-CH=CH
2
R
9Be selected from C
1-3Alkyl, C
1-3Alkoxyl group and-SO
3M;
A is selected from 0 and 1;
B is selected from 0,1 and 2,
M is hydrogen, sodium or potassium.
2. the described red reactive dye composition of claim 1 is characterized in that, the X in the general formula (1) is H, R
1, R
2, R
3, R
4Be independently selected from respectively H ,-CH
3,-OCH
3With-SO
3M, R
1And R
2Lay respectively at-ortho position or a position of N=N-group R
3And R
4Lay respectively at-ortho position or a position of N=N-group, M is hydrogen, sodium or potassium, two-SO in the general formula (1)
2Y group lays respectively at-contraposition or a position of N=N-group.
3. the described red reactive dye composition of claim 2 is characterized in that the dyestuff of general formula (1) expression is selected from the compound of representing with following structural formula:
Dyestuff Ia
Dyestuff Ib and
Dyestuff Ic.
4. the described red reactive dye composition of claim 1 is characterized in that, the X in the general formula (2) is H, R
5, R
6, R
7, R
8Be independently selected from respectively H ,-CH
3,-OCH
3With-SO
3M, R
5And R
6Lay respectively at-ortho position or a position of N=N-group R
7And R
8Lay respectively at-ortho position or a position of N=N-group, M is hydrogen, sodium or potassium, two-SO
2Y group lays respectively at-ortho position or a position of N=N-group.
5. the described red reactive dye composition of claim 4 is characterized in that, the dyestuff of general formula (2) expression is selected from the compound of representing with following structural formula:
Dyestuff IIa
Dyestuff IIb and
Dyestuff IIc.
6. the described red reactive dye composition of claim 1 is characterized in that, the X in the general formula (3)
1Be Cl, R
9Be selected from-CH
3,-OCH
3With-SO
3M, R
9The b of group is selected from 0,1 and 2 respectively; R
9Group is separately located in respectively on the benzene nucleus-ortho position or the contraposition of N=N-group, or be positioned on the benzene nucleus 1 and 5.
7. the described red reactive dye composition of claim 1 is characterized in that, in the general formula (3)-SO
2Y group is positioned at-ortho position or a position of NH-group;-SO
2Y
1Respectively independently or be positioned on the benzene nucleus-ortho position or the contraposition of N=N-group, or be positioned on the benzene nucleus 1 or 5, wherein a is selected from 0 and 1 respectively.
8. claim 6 or 7 described red reactive dye compositions is characterized in that, the dyestuff of general formula (3) expression is selected from the compound of representing with following structural formula:
Dyestuff IIIa and
Dyestuff IIIb.
9. the described red reactive dye composition of claim 1 is characterized in that, the weight ratio of the dyestuff of the dyestuff of general formula (1) expression and general formula (2) expression and the dyestuff of general formula (3) expression is 35～80: 10～20: 10～45.
10. each described red reactive dye composition is applied to contain dyeing on carboxyl and/or the formamido-material among the claim 1-9.
11. application as claimed in claim 10 is characterized in that, describedly contains carboxyl and/or the formamido-material is to contain carboxyl and/or formamido-filamentary material.
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|---|---|---|---|
| CN2007100418313A CN101323710B (en) | 2007-06-11 | 2007-06-11 | Red reactive dye composition and dyeing application thereof |
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|---|---|---|---|
| CN2007100418313A CN101323710B (en) | 2007-06-11 | 2007-06-11 | Red reactive dye composition and dyeing application thereof |
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|---|---|
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| CN101323710B true CN101323710B (en) | 2011-05-04 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013189815A1 (en) * | 2012-06-18 | 2013-12-27 | Dystar Colours Distribution Gmbh | Metal free reactive dyes, process for the production thereof and their use |
| WO2013189814A1 (en) * | 2012-06-18 | 2013-12-27 | Dystar Colours Distribution Gmbh | Metal-free reactive dyes, process for the production thereof and their use |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102344693B (en) * | 2011-08-17 | 2013-07-24 | 无锡润新染料有限公司 | Novel composite active cardinal dye and manufacturing method thereof |
| CN106700649A (en) * | 2016-12-30 | 2017-05-24 | 江苏安诺其化工有限公司 | Preparation method of red dye |
| CN106752083A (en) * | 2016-12-30 | 2017-05-31 | 江苏安诺其化工有限公司 | A kind of orchil, dye material composition and application |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1274734A (en) * | 1999-05-19 | 2000-11-29 | 德意志戴斯达纺织品及染料两合公司 | Orange and deep red mixture of reactive dyes |
| CN1807518A (en) * | 2006-01-26 | 2006-07-26 | 浙江龙盛集团股份有限公司 | Composite reactive red dye and preparation thereof |
-
2007
- 2007-06-11 CN CN2007100418313A patent/CN101323710B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1274734A (en) * | 1999-05-19 | 2000-11-29 | 德意志戴斯达纺织品及染料两合公司 | Orange and deep red mixture of reactive dyes |
| CN1807518A (en) * | 2006-01-26 | 2006-07-26 | 浙江龙盛集团股份有限公司 | Composite reactive red dye and preparation thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013189815A1 (en) * | 2012-06-18 | 2013-12-27 | Dystar Colours Distribution Gmbh | Metal free reactive dyes, process for the production thereof and their use |
| WO2013189814A1 (en) * | 2012-06-18 | 2013-12-27 | Dystar Colours Distribution Gmbh | Metal-free reactive dyes, process for the production thereof and their use |
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| Publication number | Publication date |
|---|---|
| CN101323710A (en) | 2008-12-17 |
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