CN102304299A - Tricolor reactive dye composition and application thereof in dyeing fibers - Google Patents
Tricolor reactive dye composition and application thereof in dyeing fibers Download PDFInfo
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- CN102304299A CN102304299A CN201110264330A CN201110264330A CN102304299A CN 102304299 A CN102304299 A CN 102304299A CN 201110264330 A CN201110264330 A CN 201110264330A CN 201110264330 A CN201110264330 A CN 201110264330A CN 102304299 A CN102304299 A CN 102304299A
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Abstract
The invention relates to a reactive dye composition which is compounded from one or more dye compounds disclosed as general formula (1), one or more dye compounds disclosed as general formula (2) and one or more dye compounds disclosed as general formula (3). The invention provides a reactive dye composition with different colors, such as grey, brown, dark green and the like. The reactive dye composition provided by the invention has favorable dyeing reproducibility and excellent color fastness, especially color fastness to sunlight. The reactive dye composition contains the following components: general formula (1), general formula (2) and general formula (3).
Description
Technical field
The present invention relates to the three primary colors reactive dye compositions and in the tint applications of filamentary material.Particularly, the present invention relates to grey, brown and blackish green reactive dye compositions and tint applications thereof.
Background technology
In recent years, reactive dyestuffs are widely used in the dyeing of the material of cellulosic fibre or cellulose fiber.
The dyeing practice of reactive dyestuffs shows; Adopt two or more reactive dyestuffs with color and luster or heterochromatic pool; Reactive dye compositions or the mixture composite with certain proportion have the dyeing behavior more excellent than its component dyestuff, thereby satisfy the harsh day by day demand of printing and dyeing industry.
The practice of industrial application shows; Adopt yellow, red and blue reactive dyestuffs kind or its composition as the three primary colors dyestuff through test; Carry out compositely in varing proportions, can make different color and lusters, application performance excellent reactive dye compositions or mixture.These different color and lusters, for example black, grey, brown, blackish green, navy blue etc.These color and lusters use the single-activity dyestuff often to be difficult to reach the ideal effect, or still untappedly go out this type dye species.
In above-mentioned development research practice, most important as the selection of trichromatic dyestuff or its composition.Because affinity, reactivity, dyeing kinetics and temperature dependency as trichromatic dyestuff or its composition are different, usually can produce problems such as color spot, aberration and reproducibility, level-dyeing property difference.
Make up the patent of dyestuffs from numerous three primary colors of having delivered and see, most patents serve as the application purpose with the preparation black and active dye all.These black and active dye compositions or mixture or be good at the fastness excellence, or good with dyeing behavior, satisfy the printing and dyeing demand and be good at.See that from development trend the development research of black and active dye composition is still continuing, still in constantly improving.C.I. reactive black 5 is usually as the blue dyes component in the black and active dye composition.
Regrettably, in the patent of the numerous three primary colors black combination dyestuffs of having delivered, seldom relate to the content of three primary colors combined grey, brown and blackish green reactive dye compositions.
The present invention is intended to develop three primary colors reactive dyestuffs composite grey, brown and blackish green reactive dye compositions with good dyeing circulation ratio and dyeing behavior of excellence.
When selecting three primary colors reactive dyestuffs kind, the inventor notices following Yellow active dye kind:
This reactive dyestuffs kind coloured light is gorgeous, has excellent dyefastness.Shanghai refined fortune company once delivered patent (CN101074324 (2007)), and its dyeing behavior is made further investigation evaluation.
Above-mentioned Yellow active dye kind only appears in the patent application of CN 1118796 (1996) black reactive dye mixture (Hoechst) as the yellow color component in the three primary colors composition.The present invention selects above-mentioned Yellow active dye kind as the yellow dyes component.
The present invention in a large number of people on a trial basis, pleasantly surprised to find a comprehensive color fastness excellent blue triphenyl two
triazine reactive dye composition of the present invention the three primary colors blue reactive dye components, can be successfully achieved the expected effects of the present invention .
The general formula of blueness, redness and the Yellow active dye of three primary colors composition reactive dye compositions of the present invention is following:
The blue active dye general formula is:
General formula (1)
The general formula of red reactive dyes is:
General formula (2)
The general formula of Yellow active dye is:
General formula (3)
The inventor finds that through test tricolor dye component of the present invention has good consistency pleasantly surprisedly.Grey of the present invention, brown and blackish green reactive dye compositions have good dye stability and excellent each item dyefastness.
The inventor does not see redness of the present invention, yellow and patent and the relevant report of blue three primary colors reactive dyestuffs combination as grey, coffee color, blackish green reactive dye compositions.The inventor does not also see redness of the present invention, yellow and the patent and relevant report of blue three primary colors reactive dyestuffs combination as the black and active dye composition.
Summary of the invention
The inventor is through a large amount of experimental studies; Be surprised to find the dye composition and the dye composition of one or more general formulas (2) expression and the reactive dye compositions of the dye composition that one or more general formulas (3) are represented that comprise one or more general formulas (1) expression, have very excellent dyeing behavior and each item dyefastness.
Adopt the dye composition of above-mentioned general formula (1), general formula (2) and general formula (3) expression; Piece together mixed or composite in certain proportion; The reactive dye compositions of different color and lusters such as black, grey, brown, green be can make, printing and dyeing industry increasingly stringent and harsh demand satisfied.
Reactive dye compositions that it should be noted that the different color and lusters that the present invention is made up of three primary colors has excellent dye stability and each item dyefastness, especially sun-resistant fastness.
Three primary colors reactive dye compositions provided by the invention comprises dyestuff and the dyestuff of one or more general formulas (2) expression and the dyestuff of one or more general formulas (3) expression of one or more general formulas of blended (1) expression by a certain percentage.
General formula (1)
In the formula:
R
1And R
2Be H or Cl independently respectively;
Y
1And Y
2Be independently-CH respectively
2CH
2OSO
3M or-CH=CH
2
Q is-OSO
3M,
Or-NHCO-V-COOM;
W is-(CH
2)
n-group;
V is-(CH
2)
m-group;
N and m are respectively 1～4 integer independently;
M is H or alkali metal cation.
General formula (2)
In the formula:
Y
3And Y
4Be independently-CH respectively
2CH
2OSO
3M or-CH=CH
2
R
3, R
4, R
5And R
6Be H, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or-SO
3M;
R
7Be H or C
1-C
4Alkyl;
X
1For H, Cl, F ,-CH
2SO
3M or-CH
2COOM;
M is H or alkali metal cation;
General formula (3)
In the formula:
X
2Be Cl, F or HNCN;
Y
5And Y
6Be independently-CH respectively
2CH
2OSO
3M or-CH=CH
2
R
8And R
9Be H, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or-SO
3M;
T is 0 or 1;
L is 0 or 1;
M is H or alkali metal cation.
The present invention also provides the application of above-mentioned reactive dye compositions at the dyeing aspect of hydroxyl and/or formamido-material, particularly filamentary material.
The practical implementation method
In the reactive dye compositions of the present invention, comprise the dye composition of one or more general formulas (1) expression, the dye composition of one or more general formulas (2) expression and the dye composition of one or more general formulas (3) expression.
In dye composite of the present invention, 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: 10～80: 5～60: 5～60, be preferably 20～70: 15～50: 15～50; More preferably 20～60: 10～30: 20～40.
One preferred embodiment in, in the general formula (1), when Q does
The time ,-SO
3The M group is positioned on this benzene nucleus-the NH-W-group between position, ortho position or contraposition.
Another preferred embodiment in, in the general formula (1), when Q does
The time ,-SO
3The M group is positioned on this benzene nucleus-the NH-W-NHCO group between position, ortho position or contraposition.
One preferred embodiment in, in the general formula (2)-SO
2Y
3Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of N=N-group; In the general formula (2)-SO
2Y
4Group when p=1, is positioned on the benzene nucleus
The ortho position of group, a position or contraposition.
Another preferred embodiment in, the R in the general formula (2)
3, R
4, R
5And R
6Group, be separately located in respectively separately on the benzene nucleus-the N=N-group or
The ortho position of group, a position or contraposition.
One preferred embodiment in, in the dyestuff of general formula (3) expression, R
8Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of N=N-group; In the general formula (3)-SO
2Y
5Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of N=N-group.
Another preferred embodiment in, the R in the dyestuff of general formula (3) expression
9Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH-group; In the dyestuff of general formula (3) expression-SO
2Y
6Group when l=1, is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH-group.
The dye composition of general formula (1) expression for example comprises following instance:
Dyestuff 1-1
Dyestuff 1-2
Dyestuff 1-3
Dyestuff I-4
Dyestuff I-5
Dyestuff I-6
Dyestuff I-7 or
Dyestuff I-8.
The dye composition of general formula (2) expression for example comprises following instance:
Dyestuff 2-1
Dyestuff 2-2
Dyestuff 2-3
Dyestuff 2-4
Dyestuff 2-5
Dyestuff 2-6
Dyestuff 2-7 or
Dyestuff 2-8.
The dye composition of general formula (3) expression for example comprises following instance:
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 dye composition of the dye composition of the dye composition of general formula (1) expression, general formula (2) expression and general formula (3) expression all is a known dye.
The dye composition of general formula (1) expression, its structural formula and synthesis method can be consulted following patent:
US?4705524(1987)(Hoechst)
US?4774333(1988)(Hoechst)
US?4782150(1988)(Hoechst)
US?4785098(1988)(Hoechst)
US?4845213(1989)(Bayer)
US?4885385(1989)(Hoechst)
The dye composition of general formula (2) expression, its structural formula and synthesis method can be consulted following patent:
US?5250670(1993)(Hoechst)
US?5292870(1994)(ICI)
US?5665124(1997)(Bayer)
CN 1503828 (2004) (Ke Laienante finance (BVI) company limited)
US7091328(2006)(Clariant?Finanace(BVI)Limited)
The dye composition of general formula (3) expression, its structural formula and synthesis method can be consulted following patent:
CN 101074324 (2007) (the refined fortune in Shanghai)
CN?1443219(2003)(Dystar)
CN?1118796(1996)(Hoechst)
WO?02/08341(2002)(Dystar)
The full content of above-mentioned document is referred among the present invention.
Reactive dye compound 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, like sodium sulfate or Repone K, content 0～10 weight %, preferred 2～6 weight %; The pH regulator agent, like 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 be 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 reactive dye compositions of the present invention comprises above-mentioned general formula (1) dye composition, general formula (2) dye composition and general formula (3) dye composition is mixed by the weight ratio of regulation.Mix available various ordinary method, like the mechanically mixing method.During mixing, general formula (1) dye composition, general formula (2) dye composition and general formula (3) dye composition 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.
Reactive dye compositions 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.
Reactive dye compositions of the present invention can be applied to filamentary material and is affixed 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
Each item testing method of embodiment
Each item performance of present embodiment is tested by following each item testing method
1, dying-stable property testing end to end: by pad dyeing dyeing preparation dye liquor; Adopt the dyeing of pad dyeing dyeing; After will padding 10 cloth continuously with a dye liquor; Use the Datacolor color measurement instrument; Test the aberration DE value between a piece of cloth and the tenth cloth; The DE value is more little, and the expression dye stability is good more.
2, RF value test: filter paper is cut into 30 centimetres of sizes of 4x, the one of which end is soaked places dye liquor, start line is indicated in filter paper and liquid level junction, and ascending development takes out after 30 minutes and dries, and the last line height of line height and water calculates its Rf value on the measurement dye liquor.
Line height on line height/moisture content on the Rf=dyestuff;
The Rf value is low in expression dyestuff substantivity more than 0.9, good level-dyeing property.
3, photosensitive test: will dye good fabric constant artificial light held 2 hours, and use the Datacolor color measurement instrument, test light is according to the aberration DE of front and back, and the DE value is more little, representes that photosensitivity is more little.
4, colour fastness to perspiration test: measure by international standard ISO 105-E04.
5, fastness to soaping test: measure by international standard ISO 105-C10.
6, color fastness to water test: measure by international standard ISO 105-E01.
7, colour fasteness to sunlight test: measure by international standard ISO 105-B02.
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 red reactive dye compositions of the embodiment of the invention with various dye components.
" % " in the table 1 all representes weight %, is benchmark with the gross weight of dye composite.
Table 1
| Numbering | The reactive dyestuffs title | Form |
| 1 | A | 40% dyestuff 1-1+20% dyestuff 2-1+40% dyestuff 3-1 |
| 2 | B | 20% dyestuff 1-1+40% dyestuff 2-1+40% dyestuff 3-1 |
| 3 | C | 35% dyestuff 1-1+15% dyestuff 2-1+50% dyestuff 3-1 |
| 4 | D | 40% dyestuff 1-3+20% dyestuff 2-1+40% dyestuff 3-2 |
| 5 | E | 20% dyestuff 1-3+40% dyestuff 2-1+40% dyestuff 3-2 |
| 6 | F | 35% dyestuff 1-3+15% dyestuff 2-1+50% dyestuff 3-2 |
| 7 | G | 20% dyestuff 1-1+50% dyestuff 2-1+30% dyestuff 3-1 |
| 8 | H | 70% dyestuff 1-1+15% dyestuff 2-1+15% dyestuff 3-1 |
Embodiment 1
The coloured light of three primary colors reactive dye compositions of the present invention
The coloured light of reactive dye compositions of the present invention can be adjusted the ratio of general formula (1) dye composition, general formula (2) dye composition and general formula (3) dye composition as required; Reach responsive colour systems such as grey, blackish green, brown, brown, thereby realize that dyeing and finishing adds the dye stability of these responsive colour systems in man-hour.Write down the coloured light that each embodiment forms dyestuff in the table 1.
Table 1
Embodiment 2
Pad dyeing is the dying-stable property testing end to end
Measure the dye stability end to end of following dyestuff as stated above, test result is recorded in the table 2
Table 2
Visible by table 2:
Three primary colors reactive dye compositions of the present invention has good dye stability end to end.
Embodiment 3
The test of Rf value
Measure the Rf value of following dyestuff as stated above, test result is recorded in the table 3
Table 3
Visible by table 3:
Three primary colors reactive dye compositions of the present invention, the RF value is in close proximity to 1, representes that its dyestuff substantivity is lower, and level-dyeing property is better.
Embodiment 4
The photosensitivity test
Measure the photosensitivity of following dyestuff as stated above, test result is recorded in the table 4
Table 4
Visible by table 4:
Three primary colors reactive dye compositions of the present invention has excellent photosensitivity.
Embodiment 5
Colour fastness to perspiration
Measure the colour fastness to perspiration of following dyestuff as stated above, test result is recorded in the table 5
Table 5
Visible by table 5:
Three primary colors reactive dye compositions of the present invention has good fastness to perspiration.
Embodiment 6
Fastness to soaping and color fastness to water
Measure the fastness to soaping and the color fastness to water of following dyestuff as stated above, test result is recorded in the table 6
Table 6
Visible by table 6:
Three primary colors reactive dye compositions of the present invention has good fastness to soaping and color fastness to water.
Embodiment 7
Sun-resistant fastness
Measure the sun-resistant fastness of following dyestuff as stated above, test result is recorded in the table 7
Table 7
Visible by table 7:
Three primary colors reactive dye compositions of the present invention has very excellent sun-resistant fastness.
Claims (10)
1. reactive dye compositions, this reactive dye compositions comprise the dye composition of one or more general formulas (1) expression, the dye composition of one or more general formulas (2) expression, and the dye composition of one or more general formulas (3) expression:
General formula (1)
In the formula:
R
1And R
2Be H or Cl independently respectively;
Y
1And Y
2Be independently-CH respectively
2CH
2OSO
3M or-CH=CH
2
Q is-OSO
3M,
Or-NHCO-V-COOM;
W is-(CH
2)
n-group;
V is-(CH
2)
m-group;
N and m are respectively 1～4 integer independently;
M is H or alkali metal cation;
General formula (2)
In the formula:
Y
3And Y
4Be independently-CH respectively
2CH
2OSO
3M or-CH=CH
2
R
3, R
4, R
5And R
6Be H, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or-SO
3M;
R
7Be H or C
1-C
4Alkyl;
X
1For H, Cl, F ,-CH
2SO
3M or-CH
2COOM;
M is H or alkali metal cation;
General formula (3)
In the formula:
X
2Be Cl, F or HNCN;
Y
5And Y
6Be independently-CH respectively
2CH
2OSO
3M or-CH=CH
2
R
8And R
9Be H, C independently respectively
1-C
4Alkyl, C
1-C
4Alkoxyl group or-SO
3M;
T is 0 or 1;
L is 0 or 1;
M is H or alkali metal cation.
2. the described reactive dye compositions of claim 1; Its characteristic is; One or more dye compositions of general formula (1) expression: one or more dye compositions of general formula (2) expression: one or more dye compositions of general formula (3) expression weight ratio be 10～80: 5～60: 5～60, be preferably 20～70: 15～50: 10～50.
3. the described reactive dye compositions of claim 1 is characterized in that, in the general formula (1), when Q does
The time ,-SO
3The M group is positioned on this benzene nucleus-the NH-W-group between position, ortho position or contraposition; In the general formula (1), when Q does
The time ,-SO
3The M group is positioned on this benzene nucleus-the NH-W-NHCO group between position, ortho position or contraposition.
4. the described reactive dye compositions of claim 1, its characteristic be, in the general formula (2)-SO
2Y
3Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of N=N-group; In the general formula (2)-SO
2Y
4Group when p=1, is positioned on the benzene nucleus
The ortho position of group, a position or contraposition; R in the general formula (2)
3, R
4, R
5And R
6Group, be separately located in respectively separately on the benzene nucleus-the N=N-group or
The ortho position of group, a position or contraposition.
5. the described reactive dye compositions of claim 1, its characteristic be, in the general formula (3)-SO
2Y
5Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of N=N-group; In the general formula (3)-SO
3The M group when t=1, is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH-group; In the general formula (3)-SO
2Y
6Group when 1=1, is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH-group.
6. the described reactive dye compositions of claim 1, its characteristic is, the R in the general formula (3)
8Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of N=N-group R
9Group is positioned on the benzene nucleus-ortho position, a position or the contraposition of NH-group.
7. the described reactive dye compositions of claim 1, its characteristic are that the dye composition of general formula (1) expression is:
Dyestuff 1-1
Dyestuff 1-2
Dyestuff 1-3
Dyestuff I-4
Dyestuff I-5
Dyestuff I-6
Dyestuff I-7 or
Dyestuff I-8.
8. the described reactive dye compositions of claim 1, its characteristic are that the dye composition of general formula (2) expression is:
Dyestuff 2-1
Dyestuff 2-2
Dyestuff 2-3
Dyestuff 2-4
Dyestuff 2-5
Dyestuff 2-6
Dyestuff 2-7 or
Dyestuff 2-8.
9. the described reactive dye compositions of claim 1, its characteristic are that the dye composition of general formula (3) expression is:
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.
In the claim 1～9 each described reactive dye compositions in the application of the dyeing aspect of hydroxyl and/or formamido-material, particularly filamentary material.
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|---|---|---|---|
| CN201110264330.8A CN102304299B (en) | 2011-09-07 | 2011-09-07 | Tricolor reactive dye composition and application thereof in dyeing fibers |
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|---|---|---|---|
| CN201110264330.8A CN102304299B (en) | 2011-09-07 | 2011-09-07 | Tricolor reactive dye composition and application thereof in dyeing fibers |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104277492A (en) * | 2014-09-28 | 2015-01-14 | 天津德凯化工股份有限公司 | Reactive red dye and preparation method thereof |
| CN104312201A (en) * | 2014-09-28 | 2015-01-28 | 天津德凯化工股份有限公司 | Red reactive dye for nylon |
| CN105239351A (en) * | 2015-11-09 | 2016-01-13 | 无锡红豆居家服饰有限公司 | Coffee reactive dye composition and dyeing process |
| CN105348854A (en) * | 2014-08-22 | 2016-02-24 | 湖北丽源科技股份有限公司 | Blue reactive dye |
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| 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 |
| CN1942528A (en) * | 2004-04-06 | 2007-04-04 | 克莱里安特财务(Bvi)有限公司 | Process for dyeing |
| CN101074324A (en) * | 2006-05-16 | 2007-11-21 | 上海雅运纺织化工有限公司 | Yellow active dye composition and its use |
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2011
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|---|---|---|---|---|
| US5356441A (en) * | 1992-09-11 | 1994-10-18 | Sumitomo Chemical Company, Limited | Reactive dye composition and method for dyeing or printing fiber materials using the same |
| 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 |
| CN1942528A (en) * | 2004-04-06 | 2007-04-04 | 克莱里安特财务(Bvi)有限公司 | Process for dyeing |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105348854A (en) * | 2014-08-22 | 2016-02-24 | 湖北丽源科技股份有限公司 | Blue reactive dye |
| CN105348854B (en) * | 2014-08-22 | 2017-03-22 | 湖北丽源科技股份有限公司 | Blue reactive dye |
| CN104277492A (en) * | 2014-09-28 | 2015-01-14 | 天津德凯化工股份有限公司 | Reactive red dye and preparation method thereof |
| CN104312201A (en) * | 2014-09-28 | 2015-01-28 | 天津德凯化工股份有限公司 | Red reactive dye for nylon |
| CN105239351A (en) * | 2015-11-09 | 2016-01-13 | 无锡红豆居家服饰有限公司 | Coffee reactive dye composition and dyeing process |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102304299B (en) | 2014-03-12 |
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