CN102304299B - 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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- CN102304299B CN102304299B CN201110264330.8A CN201110264330A CN102304299B CN 102304299 B CN102304299 B CN 102304299B CN 201110264330 A CN201110264330 A CN 201110264330A CN 102304299 B CN102304299 B CN 102304299B
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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 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 containing cellulose fiber.
The Dyeing Practice of reactive dyestuffs shows, adopt two or more with the reactive dyestuffs in color and luster or heterochromatic pool, with the composite reactive dye compositions of certain proportion or mixture, there is the dyeing behavior more excellent compared with its component dyestuff, thereby meet the day by day harsh demand of printing and dyeing industry.
The practice of industrial application shows, by test, adopt yellow, red and blue reactive dyestuffs kind or its composition as three primary colors dyestuff, carry out in varing proportions compositely, can make reactive dye compositions or the mixture of different color and lusters, application performance excellence.These different color and lusters, such as black, grey, brown, blackish green, navy blue etc.These color and lusters, are used single-activity dyestuff to be often difficult to the effect that reaches desirable, or not yet develop this class 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 the problems such as color spot, aberration and reproducibility, level-dyeing property be poor.
From the patent of the numerous three primary colors combination dyestuffs delivered, most patents all be take and are prepared black and active dye as application object.These black and active dye compositions or mixture or be good at fastness excellence, or good with dyeing behavior, meet printing and dyeing demand and be good at.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 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, the brown and blackish green reactive dye compositions with good reproducibility and excellent dyeing behavior.
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 Ya Yun company once delivered patent (CN101074324 (2007)), and its dyeing behavior is made to further investigation evaluation.
Above-mentioned Yellow active dye kind, as the yellow color component in three primary colors composition, only appears in the patent application of CN 1118796 (1996) black reactive dye mixture (Hoechst).The present invention selects above-mentioned Yellow active dye kind as yellow dyes component.
The inventor, on the basis of lot of experiments, finds to adopt the blue triphen two of comprehensive dyefastness excellence pleasantly surprisedly
piperazine reactive dyestuffs, as the blue color component of three primary colors combined activity dyestuff of the present invention, can successfully reach desired result 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 as follows:
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 by test pleasantly surprisedly, and tricolor dye component of the present invention has good consistency.Grey of the present invention, brown and blackish green reactive dye compositions have good dye stability and excellent every dyefastness.
The inventor has no redness of the present invention, yellow and the combination of blue three primary colors reactive dyestuffs as patent and the relevant report of grey, coffee color, blackish green reactive dye compositions.The inventor also has no redness of the present invention, yellow and the combination of blue three primary colors reactive dyestuffs as patent and the relevant report of black and active dye composition.
Summary of the invention
The inventor studies by lot of experiments, 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) represent that comprise that one or more general formulas (1) represent, there is very excellent dyeing behavior and every dyefastness.
The dye composition that adopts above-mentioned general formula (1), general formula (2) and general formula (3) to represent, carry out in certain proportion blending or composite, the reactive dye compositions that can make black, grey, the different color and lusters such as brown, green, meets printing and dyeing industry increasingly stringent and harsh demand.
Reactive dye compositions that it should be noted that the different color and lusters that the present invention is comprised of three primary colors has excellent dye stability and every dyefastness, especially sunlight fastness.
Three primary colors reactive dye compositions provided by the invention comprises the dyestuff of the dyestuff of one or more general formulas (1) expression mixing by a certain percentage and the dyestuff of one or more general formulas (2) expression and one or more general formulas (3) expression.
General formula (1)
In 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 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
7for 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 formula:
X
2for 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.
Specific implementation method
In reactive dye compositions of the present invention, comprise dye composition, the dye composition of one or more general formulas (2) expression and the dye composition 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: 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 general formula (1), when Q is
time ,-SO
3position, ortho position or contraposition between be positioned on this benzene nucleus-NH-W-group of M group.
Another preferred embodiment in, in general formula (1), when Q is
time ,-SO
3position, ortho position or contraposition between be positioned on this benzene nucleus-NH-W-NHCO group of M group.
One preferred embodiment in, in general formula (2)-SO
2y
3group, ortho position, a position or the contraposition of be positioned on benzene nucleus-N=N-group; In general formula (2)-SO
2y
4group, when p=1, is positioned on benzene nucleus
the ortho position of group, a position or contraposition.
Another preferred embodiment in, the R in general formula (2)
3, R
4, R
5and R
6group, be separately located in respectively separately on benzene nucleus-N=N-group or
the ortho position of group, a position or contraposition.
One preferred embodiment in, in the dyestuff that general formula (3) represents, R
8ortho position, a position or the contraposition of be positioned on benzene nucleus-N=N-group of group; In general formula (3)-SO
2y
5group, ortho position, a position or the contraposition of be positioned on benzene nucleus-N=N-group.
Another preferred embodiment in, the R in the dyestuff that general formula (3) represents
9ortho position, a position or the contraposition of be positioned on benzene nucleus-NH-group of group; In the dyestuff that general formula (3) represents-SO
2y
6group, ortho position, a position or the contraposition of when l=1, be positioned on benzene nucleus-NH-group.
The dye composition that general formula (1) represents, for example, comprise following example:
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 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
Dyestuff 2-6
Dyestuff 2-7 or
Dyestuff 2-8.
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 dye composition that the dye composition that the dye composition that general formula (1) represents, general formula (2) represent and general formula (3) represent is all known dye.
The dye composition that general formula (1) represents, its structural formula and synthetic 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 that general formula (2) represents, its structural formula and synthetic 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 that general formula (3) represents, its structural formula and synthetic 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 in the present invention.
Reactive dye compositions 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, preferred 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 comprised 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 weight ratio is in accordance with regulations mixed.Mix available various ordinary method, as 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 suitable shredder as ball mill or needle mill in and in kneader or mixing machine, carry out.
Reactive dye compositions of the present invention is suitable for dyeing and various materials widely thereof, particularly contain the material of 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 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, dye stability test end to end: by pad dyeing dyeing preparation dye liquor, adopt the dyeing of pad dyeing dyeing, to pad continuously after 10 cloth with a dye liquor, use Datacolor color measurement instrument, test the aberration DE value between a piece of cloth and the tenth cloth, DE value is less, represents that dye stability is better.
2, RF value test: filter paper is cut into 30 centimetres of sizes of 4x, its one end is soaked and is placed in dye liquor, start line is indicated in filter paper and liquid level junction, and ascending development took out and dries after 30 minutes, on measurement dye liquor, the upper line height of line height and water, calculates its Rf value.
Line height on line height/moisture content on Rf=dyestuff;
Rf value more than 0.9 is representing that dyestuff substantivity is low, good level-dyeing property.
3, photosensitive test: the fabric having dyed is placed 2 hours under constant artificial light, used Datacolor color measurement instrument, test light is according to the aberration DE of front and back, and DE value is less, represents that photosensitivity is less.
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 according to the form below 1 and consumption thereof evenly mix various dye components by ordinary method in this area, the various red reactive dye compositions of the preparation embodiment of the present invention.
" % " in table 1 all represents % by weight, and the gross weight of dye composite of take is benchmark.
Table 1
| Numbering | 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 the responsive colour systems such as grey, blackish green, brown, brown, thereby realize the dye stability that dyeing and finishing adds these responsive colour systems in man-hour.In table 1, recorded the coloured light that each embodiment forms dyestuff.
Table 1
Embodiment 2
Pad dyeing dye stability test end to end
The dye stability end to end that is determined as follows as stated above dyestuff, test result is recorded in table 2
Table 2
From 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
The Rf value that is determined as follows as stated above dyestuff, test result is recorded in table 3
Table 3
From table 3:
Three primary colors reactive dye compositions of the present invention, RF value is in close proximity to 1, represents that its dyestuff substantivity is lower, and level-dyeing property is better.
Embodiment 4
Photosensitivity test
The photosensitivity that is determined as follows as stated above dyestuff, test result is recorded in table 4
Table 4
From table 4:
Three primary colors reactive dye compositions of the present invention, has excellent photosensitivity.
Embodiment 5
Colour fastness to perspiration
The colour fastness to perspiration that is determined as follows as stated above dyestuff, test result is recorded in table 5
Table 5
From 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
The fastness to soaping and the color fastness to water that are determined as follows as stated above dyestuff, test result is recorded in table 6
Table 6
From table 6:
Three primary colors reactive dye compositions of the present invention has good fastness to soaping and color fastness to water.
Embodiment 7
Sunlight fastness
The sunlight fastness that is determined as follows as stated above dyestuff, test result is recorded in table 7
Table 7
From table 7:
Three primary colors reactive dye compositions of the present invention has very excellent sunlight fastness.
Claims (7)
1. a reactive dye compositions, this reactive dye compositions is by the dye composition of one or more general formulas (1) expression, the dye composition that one or more general formulas (2) represent, and the dye composition of one or more general formulas (3) expression and the optional conventional dye additive composition using in dyeing and dye formulations:
In 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;
In 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
7for H or C
1-C
4alkyl;
X
1for H, Cl or F;
M is H or alkali metal cation;
The dye composition that general formula (3) represents is:
One or more dye compositions that general formula (1) represents: one or more dye compositions that general formula (2) represents: one or more dye compositions that general formula (3) represents weight ratio be 10～80:5～60:5～60.
2. reactive dye compositions claimed in claim 1, its characteristic is, one or more dye compositions that general formula (1) represents: one or more dye compositions that general formula (2) represents: one or more dye compositions that general formula (3) represents weight ratio be 20～70:15～50:10～50.
3. reactive dye compositions claimed in claim 1, its characteristic is, in general formula (2)-SO
2y
3group, ortho position, a position or the contraposition of be positioned on benzene nucleus-N=N-group; In general formula (2)-SO
2y
4group, when p=1, is positioned on benzene nucleus
the ortho position of group, a position or contraposition; R in general formula (2)
3, R
4, R
5and R
6group, be separately located in respectively separately on benzene nucleus-N=N-group or
the ortho position of group, a position or contraposition.
4. reactive dye compositions claimed in claim 1, its characteristic is, the dye composition that general formula (1) represents is:
5. reactive dye compositions claimed in claim 1, its characteristic is, the dye composition that general formula (2) represents is:
6. the application of the reactive dye compositions described in any one aspect the dyeing of hydroxyl and/or formamido-material in claim 1～5.
7. application as claimed in claim 6, wherein hydroxyl and/or formamido-material are hydroxyl and/or formamido-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 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110264330.8A CN102304299B (en) | 2011-09-07 | 2011-09-07 | Tricolor reactive dye composition and application thereof in dyeing fibers |
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| Publication Number | Publication Date |
|---|---|
| CN102304299A CN102304299A (en) | 2012-01-04 |
| CN102304299B true CN102304299B (en) | 2014-03-12 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105348854B (en) * | 2014-08-22 | 2017-03-22 | 湖北丽源科技股份有限公司 | Blue reactive dye |
| 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 |
| 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 |
| 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 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
-
2011
- 2011-09-07 CN CN201110264330.8A patent/CN102304299B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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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