CN102766354B - Blue reactive dye composition and dyeing applications of same to fibers - Google Patents
Blue reactive dye composition and dyeing applications of same to fibers Download PDFInfo
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- CN102766354B CN102766354B CN201210271626.7A CN201210271626A CN102766354B CN 102766354 B CN102766354 B CN 102766354B CN 201210271626 A CN201210271626 A CN 201210271626A CN 102766354 B CN102766354 B CN 102766354B
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Abstract
The invention provides a blue reactive dye composition and dyeing applications of the same. The dye composition contains one or multiple dye compounds shown by a general formula (1), one or multiple dye compounds shown by a general formula (2) and one or multiple dye compounds shown by a general formula (3). The blue reactive dye composition is excellent in dyeing performance, good in various dyeing fastnesses and excellent in compatibility with other commonly used red and yellow reactive dyes. The general formular (1), the general formula (2) and the general formula (3) are as follows.
Description
Technical field
The present invention relates to a kind of reactive dye compositions and the tint applications at 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
Blue active dye shown in one of the component of blue active dye composition of the present invention general formula (1) is a kind of copper-containing metal Jia Za class (Formazan) dyestuff.Last century, the eighties Hoechst company announced its molecular structure and synthetic method thereof.
US 4336190（1982）（Hoechst）
US 4370145（1983）（Hoechst）
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 application practice show, there are many defects in the blue active dye shown in this class general formula (1), has a strong impact on and limit its widespread use.For example this class reactive dyestuffs solubleness is not high, and its enhancing has much room for improvement, and the application performances such as its level-dyeing property and degree of fixation are difficult satisfied dyeing requirement also.
In recent years, each major company of the world has carried out broad research to the blue active dye shown in above-mentioned general formula (1).The emphasis of research is:
1, the molecular structure of transformation dyestuff, to improving and improve the application performance of dyestuff;
2, employing and other dyestuff blendings, composition reactive dye compositions or mixture, to improving and improve the application performance of dyestuff.
Each major company is adopting and other dyestuff blending, the research of composition reactive dye compositions or mixture, and delivering thus representative patent has:
US 5704951（1998）（Hoechst）
US 5563248（1996）（Hoechst Celenese）
CN 1751103(2006) (Japanese chemical drug)
US 6991661（2006）（Dystar）
JP 1103668(1989) (Mitsubishi changes into)
JP 2001214084(2001) (Sumitomo)
US 5632783（1997）（BASF）
US 6171348（2001）（Dystar）
The inventor, in the time investigating the tint applications performance of above-mentioned dye composite or mixture, notices the reactive dye compositions that dyestuff that general formula (1) is represented and reactive black 5 series dyes form.
The patent that relates to above-mentioned composition is:
US 5632783（1997）（BASF）
US 6171348（2001）（Dystar）
US 5704951（1998）（Hoechst）
The inventor puts into practice by a large amount of tint applications, and above-mentioned reactive dye compositions really increases in dyeing behavior.But still there is defect, have much room for improvement.
The inventor, on the basis of test, is surprised to find that above-mentioned reactive dye compositions, adds three component of the dyestuff shown in general formula (3) as blue active dye composition of the present invention, can make the dyeing behavior of composition to some extent further improve.The inventor has no patent and the paper delivered and relates to this content.
Summary of the invention
The inventor, by experimental study, is surprised to find the blue active dye compound, the black-and-blue reactive dye compound of one or more general formulas (2) expression and the blue dyes composition of the blue active dye compound that one or more general formulas (3) represent that contain one or more general formulas (1) and represent and has very excellent dyeing behavior and every fastness.
What be worth proposition is, the tint applications performance of blue active dye composition of the present invention and every dyefastness, take in the length of the characteristic of its composition dyestuff concurrently, make up some defect of its composition dyestuff, particularly improve fastness ability, especially fastness to chlorine performance, and all there is obvious improvement in its level-dyeing property, consistency.Blue active dye composition of the present invention, cost of manufacture is cheap, can use with conventional red, yellow dye composition three primary colors.Can predict, blue active dye composition of the present invention has wide prospects for commercial application.
Blue active dye composition provided by the invention comprises the dye composition of one or more general formulas (1) expression of certain proportion mixing, the dye composition that one or more general formulas (2) represent, and the dye composition of one or more general formulas (3) expression:
General formula (1)
In formula:
R
1for H ,-Cl, C
1-C
4alkyl, C
1-C
4alkoxyl group or-SO
3m;
Y
1for-CH
2cH
2oSO
3m or-CH=CH
2;
M is H or alkali metal cation;
P is 0,1 or 2;
M is 0 or 1;
T is 0 or 1.
General formula (2)
In formula:
Y
2and Y
3be independently-CH respectively
2cH
2oSO
3m or-CH=CH
2;
M is H or alkali metal cation;
R
2, R
3, R
4and R
5be H, Cl, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group, sulfonic group or carboxylic acid.
General formula (3)
In formula:
R
6and R
7be H or Cl independently respectively;
Y
4and Y
5be independently-CH respectively
2cH
2oSO
3m or-CH=CH
2;
Q is-OSO
3m,
with-NHCO-V-COOM;
V is-(CH
2)
q-group;
W is-(CH
2)
n-group;
Q and n are respectively 1 ~ 4 independently;
M is H or alkali metal cation.
The present invention also provides the application of above-mentioned blue active dye composition at the dyeing aspect of hydroxyl and/or formamido-material, particularly filamentary material.
Specific implementation method
Dye combinations species of the present invention, comprise dyestuff, the dyestuff of one or more general formulas (2) expression and the dyestuff that one or more general formulas (3) represent that one or more general formulas (1) represent.
In dye composite of the present invention, the weight ratio of the dyestuff that the dyestuff that the dyestuff that general formula (1) represents and general formula (2) represent and general formula (3) represent is: 20～60:20～55:5～60, are preferably 25～50:25～50:10～50.
One preferred embodiment in, in general formula (1) left side-SO
3m group, contraposition or a position of in the time of p=1, be positioned on benzene nucleus-COO group; In the time of p=2, ortho position and the contraposition of be positioned on benzene nucleus-COO group; The middle right side of general formula (1)-SO
2y
1group is positioned on benzene nucleus-N=N---ortho position or a position of group; The middle right side of general formula (1)-SO
3m group, in the time of m=1, is positioned on benzene nucleus-N=N---ortho position or a position of group.
Another preferred embodiment in, the R of general formula (1) downside
1group, in the time of t=1, is positioned at being positioned on benzene nucleus on benzene nucleus
position or contraposition between group.
One preferred embodiment in, the R in general formula (2)
2, R
3, R
4and R
5ortho position, a position and the contraposition of be separately located in respectively on benzene nucleus-N=N-group of group.
Another preferred embodiment in, in general formula (2)-SO
2y
3with-SO
2y
4ortho position, a position and the contraposition of be separately located in respectively on benzene nucleus-N=N-group of group.
One preferred embodiment in, the Q group in general formula (3), when Q is selected from
when group ,-SO
3m group is positioned at ortho position, a position or the contraposition of W group on benzene nucleus; When Q is selected from
when group ,-SO
3ortho position, a position or the contraposition of be positioned on benzene nucleus-NHCO-group of M group.
Another preferred embodiment in, the p in general formula (3) is 0 or 1; M is 0 or 1; T is 0 or 1; N is an integer in 1 ~ 3; Q is an integer in 1 ~ 3.
The dye composition that general formula (1) represents, for example, comprise following example:
Dyestuff 1-1
Dyestuff 1-2
Dyestuff 1-3
Dyestuff 1-4
Dyestuff 1-5.
The dye composition that general formula (2) represents, for example, comprise following example:
Dyestuff 2-1
Dyestuff 2-2
Dyestuff 2-3
Dyestuff 2-4
Dyestuff 2-5 or
Dyestuff 2-6.
The dye composition that general formula (3) represents, for example, comprise following example:
Dyestuff 3-1
Dyestuff 3-2
Dyestuff 3-3
Dyestuff 3-4
Dyestuff 3-5
Dyestuff 3-6
Dyestuff 3-7 or
Dyestuff 3-8.
The reactive dye compound that general formula (1), general formula (2) and general formula (3) represent is known dye.
Structure and the synthetic method of the reactive dye compound that general formula (1) represents, see following patent:
US4336190（1982）（Hoechst）
US4370145（1983）（Hoechst）
US5028700（1991）（Hoechst）
US5563248（1996）（Hoechst）
US6143039（2000）（Dystar）
Structure and the synthetic method of the reactive dye compound that general formula (2) represents, see following patent:
JP5328626（1997）（Hoechst）
US2003/0229952(2003) (Joachim Eichhorn(DE)) etc.
Structure and the synthetic method of the reactive dye compound that general formula (3) represents, see following patent:
US4705524（1987）（Hoechst）
US4782150（1988）（Hoechst）
US4774333（1988）（Hoechst）
US4785098（1988）（Hechst）
US4845213（1989）（Bayer）
US4885385（1989）（Hoechst）
The full content of above-mentioned document is referred in 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 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, preferably 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 made up of general formula (1) dyestuff of above-mentioned weight ratio and general formula (2) dyestuff and general formula (3) dyestuff.
The preparation method of blue active dye composition of the present invention comprises above-mentioned general formula (1) dyestuff and general formula (2) dyestuff and general formula (3) dyestuff weight ratio is in accordance with regulations mixed.Mix available various ordinary method, as mechanically mixing method.When mixing, general formula (1) dyestuff and general formula (2) dyestuff and general formula (3) dyestuff can powder types, or with particle form, or exist with aqueous solution form.For example, mixing step can suitable shredder as ball mill or needle mill in and in kneader or mixing machine, carry out.
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-, more especially filamentary material, 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 be affixed 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, just dye rate and degree of exhaustion test: dye liquor preparation, by 60 ℃ of constant temperature dyeings of reactive dyestuffs.Respectively add before 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%
2, colour fastness to perspiration test: measure by international standard ISO 105-E04.
3, fastness to soaping test: measure by international standard ISO 105-C10.
4, color fastness to water test: measure by international standard ISO 105-E01.
5, colour fasteness to sunlight test: measure by international standard ISO 105-B02.
6, repeatedly wash look sex change: by home washings mode, after washing powder repeatedly washs, room temperature is dried and placed after 2 days, observes the colour-change situation of washing front and back by DYED FABRICS.
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 blue active dye compositions of the preparation embodiment of the present invention.
" % " in table 1 all represents % by weight, take the gross weight of dye composite as benchmark.
Table 1
| Numbering | Reactive dyestuffs title | Composition |
| 1 | A | 45% dyestuff 1-1+45% dyestuff 2-1+10% dyestuff 3-1 |
| 2 | B | 50% dyestuff 1-1+25% dyestuff 2-1+25% dyestuff 3-1 |
| 3 | C | 25% dyestuff 1-1+25% dyestuff 2-1+50% dyestuff 3-1 |
| 4 | D | 45% dyestuff 1-2+45% dyestuff 2-2+10% dyestuff 3-4 |
| 5 | E | 50% dyestuff 1-1+25% dyestuff 2-2+25% dyestuff 3-4 |
| 6 | F | 25% dyestuff 1-1+25% dyestuff 2-2+50% dyestuff 3-4 |
| 7 | Reference X | 50% dyestuff 1-1+50% dyestuff 2-1 |
| 8 | Reference Y | 100% dyestuff 1-1 |
| 9 | Reference U | 100% dyestuff 2-1 |
| 10 | Reference V | 100% dyestuff 3-1 |
* reference X is US5632783(1997) (BASF) cited embodiment
Embodiment 1
The coloured light of blue active dye composition of the present invention
The dyestuff color and luster that general formula (1) represents is turquoise and color and luster is more shallow, can not be used as three primary colors blue color component, and the dyestuff color and luster that general formula (2) represents is black-and-blue, and the dyestuff that general formula (3) represents is bright blue.
The coloured light of reactive dye compositions of the present invention can be adjusted the ratio of general formula (1) dyestuff and general formula (2) dyestuff and general formula (3) dyestuff as required, thereby the coloured light that makes mixture is sea blue look, can effectively form three primary colors combination with other redness, yellow dyes, improve its actual application value.
Embodiment 2
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 2
Table 2
From table 2:
The first rate of dying of blue active dye composition of the present invention is lower, and degree of exhaustion is good, has good uniform dyeing property and exhaustion rate.
Embodiment 3
Colour fastness to perspiration
The colour fastness to perspiration that is determined as follows as stated above dyestuff, test result is recorded in table 3
Table 3
From table 3:
Blue active dye composition of the present invention has excellent fastness to perspiration.
Embodiment 4
Fastness to soaping and color fastness to 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 4
Table 4
From table 4:
Blue active dye composition of the present invention has excellent fastness to soaping and color fastness to water.
Embodiment 5
Sunlight fastness
The sunlight fastness that is determined as follows as stated above dyestuff, test result is recorded in table 5
Table 5
From table 5:
Blue active dye composition of the present invention has good sunlight fastness, and experimental result shows, increases the dye component that general formula (3) represents, can improve sunlight fastness.
Embodiment 6
Repeatedly wash look sex change
Be determined as follows as stated above the repeatedly washing look sex change of dyestuff, test result is recorded in table 6
Table 6
From table 6, blue active dye composition of the present invention has advantages of that repeatedly washing look diminishes, and compared with reference dyestuff X, has splendid repeatedly washing colour stability.
Claims (8)
1. a blue active dye composition, the dye composition that the dye composition that this dye composite is represented by one or more general formulas (1), the dye composition that one or more general formulas (2) represent and one or more general formulas (3) represent and the optional dye additive that routine is used in dyeing and dye formulations form:
In formula:
R
1for H ,-Cl, C
1-C
4alkyl, C
1-C
4alkoxyl group or-SO
3m;
Y
1for-CH
2cH
2oSO
3m or-CH=CH
2;
M is H or alkali metal cation;
P is 0,1 or 2;
M is 0 or 1;
T is 0 or 1;
In formula:
Y
2and Y
3be independently-CH respectively
2cH
2oSO
3m or-CH=CH
2;
M is H or alkali metal cation;
R
2, R
3, R
4and R
5be H, Cl, C independently respectively
1-C
4alkyl, C
1-C
4alkoxyl group, sulfonic group or carboxylic acid;
The dye composition that general formula (3) represents is:
The dye composition that one or more general formulas (1) represent: the dye composition that one or more general formulas (2) represent: the weight ratio of the dye composition that one or more general formulas (3) represent is 20～60:20～55:5～60.
2. blue active dye composition claimed in claim 1, its characteristic is, the dye composition that one or more general formulas (1) represent: the dye composition that one or more general formulas (2) represent: the weight ratio of the dye composition that one or more general formulas (3) represent is 25～50:25～50:10～50.
3. 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 in the time of p=1, be positioned on benzene nucleus-COO group; In the time of p=2, ortho position and the contraposition of be positioned on benzene nucleus-COO group; The R of general formula (1) downside
1group, in the time of t=1, is positioned on benzene nucleus
position or contraposition between group; The middle right side of general formula (1)-SO
2y
1ortho position or a position of be positioned on benzene nucleus-N=N-group of group; The middle right side of general formula (1)-SO
3m group, ortho position or a position of in the time of m=1, be positioned on benzene nucleus-N=N-group.
4. blue active dye composition claimed in claim 1, its characteristic is, the R in general formula (2)
2, R
3, R
4and R
5ortho position, a position and the contraposition of be separately located in respectively on benzene nucleus-N=N-group of group; In general formula (2)-SO
2y
3with-SO
2y
4ortho position, a position and the contraposition of be separately located in respectively on benzene nucleus-N=N-group of group.
5. the blue active dye composition described in any one in claim 1～4, its characteristic is, the dye composition that general formula (1) represents is:
6. the blue active dye composition described in any one in claim 1～4, its characteristic is, the dye composition that general formula (2) represents is:
7. the application of the blue active dye composition described in any one aspect the dyeing of hydroxyl and/or formamido-material in claim 1～6.
8. application as claimed in claim 7, is characterized in that, described hydroxyl and/or formamido-material are hydroxyl and/or formamido-filamentary material.
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|---|---|---|---|
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| CN105348854B (en) * | 2014-08-22 | 2017-03-22 | 湖北丽源科技股份有限公司 | Blue reactive dye |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1568354A (en) * | 2001-10-17 | 2005-01-19 | 克莱里安特财务(Bvi)有限公司 | Trichromatic dyeing process and dye mixtures used therein |
| US20090178213A1 (en) * | 2005-07-06 | 2009-07-16 | Huntsman International Llc | Mixtures of reactive dyes and their use |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1568354A (en) * | 2001-10-17 | 2005-01-19 | 克莱里安特财务(Bvi)有限公司 | Trichromatic dyeing process and dye mixtures used therein |
| US20090178213A1 (en) * | 2005-07-06 | 2009-07-16 | Huntsman International Llc | Mixtures of reactive dyes and their use |
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Effective date of registration: 20160307 Address after: 215400 petrochemical industry zone, Port Development Zone, Taicang port, Suzhou, Jiangsu, Taicang Patentee after: Suzhou Kefaman Chemical Co. Ltd. Address before: 201812 Shanghai city Xuhui District Yindu Road No. 388 building 16 275-278 Patentee before: Shanghai Argus Textile Chemical Co., Ltd. |