CN102977632A - Compound active red dye - Google Patents
Compound active red dye Download PDFInfo
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- CN102977632A CN102977632A CN201210488621XA CN201210488621A CN102977632A CN 102977632 A CN102977632 A CN 102977632A CN 201210488621X A CN201210488621X A CN 201210488621XA CN 201210488621 A CN201210488621 A CN 201210488621A CN 102977632 A CN102977632 A CN 102977632A
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Abstract
The invention provides a compound active red dye, which is characterized by being formed by compounding the following components in parts by weight: 56-68 parts of a dye represented by the structural formula (I), 13-18 parts of a dye represented by the structural formula (II) and 15-28 parts of a dye represented by the structural formula (III). The three components comprise chlorotriazinyl, and vinyl sulfone group double-activity group; the appetency, the dye-uptake and the fixation rate to fibers are more similar; the sensitive degrees to a bath ratio and a dyeing temperature of electrolyte salts and color fixing agent alkalis are more similar; the compound active red dye has the dyeing synchronism and leveling property, higher fixation rate and outstanding deep dyeing performance, and effectively overcomes the defects of an active red dye formed by compounding active red 3BS and active orange 82, so that the dyeing quality of a cellulose fiber material is ensured. The compound active red dye has the advantages of stable performance, high solubility, high fixation rate, good dyeing synchronism, good leveling property, good tone reproducibility, and particularly outstanding deep dyeing, and is applicable to printing the cellulose fiber material.
Description
Technical field
The present invention relates to dye field, particularly a kind of composite active red dye.
Background technology
Along with the development with staining technique continually developed of cellulosic fibre kind, when using reactive dyestuffs that cellulosic fibre is dyeed, more and more higher requirement has been proposed for the application performance of reactive dyestuffs.Because after monochromatic kind dyestuff is painted to filamentary material, the integrated value of various performance index is difficult to reach gratifying effect, dyestuff such as similar reactive red 3BS structure is a kind of isodigeranyl active group (a chloro-s-triazine base and ethene sulfuryl) dyestuff, after although it is painted to cellulosic fibre material, the dyeing and weaving product have higher dyefastness, but its level-dyeing property and circulation ratio are all general, so two or more dyestuff composite usage more and more receives insider's attention and concern.
Once there was the people that reactive orange 82 is composite rear to cellulose dyeing with the dyestuff of similar reactive red 3BS structure, in performance certain improvement has been arranged, but there was two large shortcomings in this kind composite dye when cellulosic fibre material is dyeed:
1) contains a chloro-s-triazine and vinyl sulfone(RemzaolHuo Xingranliaodehuoxingjituan) active group in the reactive red 3BS molecular structure, can only dye under mesophilic condition.And contain dichloro s-triazine and vinyl sulfone(RemzaolHuo Xingranliaodehuoxingjituan) active group in reactive orange 82 molecular structures, dichloro s-triazine just can dye to cellulosic fibre material at normal temperatures, the vinyl sulfone(RemzaolHuo Xingranliaodehuoxingjituan) active group can only dye to filamentary material under mesophilic condition, that is to say that there are larger difference in reactive red 3BS and reactive orange 82 at dyeing temperature.
2) reactive red 3BS and reactive orange 82 these two kinds of dyestuffs are to avidity, dye uptake, the degree of fixation of fiber, and to the larger individual difference of susceptibility existence of salt, alkali and bath raio, also there are larger difference in solubleness, level-dyeing property and migration property.
More than 2 comparatively outstanding contradictions, when causing directly that reactive red 3BS and reactive orange 82 are composite dye to cellulosic fibre material, on dye asynchronism(-nization) and go on foot, cause coloured light poor reproducibility and high look colored rate.
Summary of the invention
The invention provides a kind of composite active red dye, the synergistic effect of this composite dye makes that it has that stable performance, solubleness are high, degree of fixation is high, the dyeing synchronism is good, good level-dyeing property, color reproducibility are good, especially has and dyes dark outstanding advantage.
The present invention realizes by following technical scheme.The present invention is a kind of composite active red dye, according to the mass fraction, a kind of composite active red dye, it is characterized in that: count by weight, it forms by dyestuff is composite shown in dyestuff shown in dyestuff shown in 56-68 part structural formula (I), the 13-18 part structural formula (II) and the 15-28 part structural formula (III):
In described structural formula (I), (II), (III),
R
1For-O CH
2CH
3,-CH
2CH
3
R
2A kind of in the following formula:
M is Na.
The dyestuff of described formula (I) is to be selected from following formula (I-1), (I-2) or compound (I-3):
The dyestuff of described formula (II) is to be selected from following formula (II-1), (II-2) or compound (II-3):
The application of described composite active red dye in the printing and dyeing of polyster fibre cellulose fiber material.
Composite active red dye of the present invention can prepare with well-known method.
As the preferred dyestuff parts by weight of formula (1) formula (II), formula (III) are obtained through mechanically mixing fully.Singlely meet formula (I), formula (II) dyestuff can prepare with known method, organizes WO2000006652 respectively it to be described such as US Patent No. 5359040 and world patent.Formula (III) dyestuff can prepare by the following method:
1) with H acid making beating, regulate PH=7.0 to dissolving with liquid caustic soda, join in the cyanuric chloride making beating liquid, regulate PH=3.5-4.0, reacted 2 hours, stand-by.
2) para-ester is joined in the said mixture solution, be warming up to T=40 ℃, keep PH=3.5-4.0, reacted 4 hours, get two contracting liquid.
3) para-ester, hydrochloric acid are added water, ice making beating 30 minutes, add 30% sodium nitrite in aqueous solution, holding temperature T=0-5 ℃, react after 1 hour and eliminate unnecessary Sodium Nitrite with thionamic acid.Aobvious colourless when starch potassium iodide paper, congo-red test paper shows blue look, and terminal point arrives, and gets diazo liquid.
4) above-mentioned diazo liquid is joined in the two contracting liquid, regulate PH=7.0-7.5, holding temperature T=8-15 ℃, react terminal point arrival after 6 hours, get coupling solution.Coupling solution is removed by filter insolubles, carry out spraying drying and namely get formula (III) dyestuff.
When the red dyestuff of composite reactive of the present invention dyes to cellulosic fibre material, generally need to add some auxiliary agents commonly used, such as dyeing accelerant (Na
2SO
4Or NaCl), laking agent (NaOH, Na
2CO
3, NaHCO
3), in order to strengthen feel, can also add softening agent, sometimes for special purposes, can also add some functional agents, such as fire retardant, electrostatic agent.Applicable dyeing process has: dip-dye, dye gigging, pad dyeing, cold rolling heap, preferably contaminate and pad dyeing.Applicable filamentary material mainly is cellulosic fibre material, and such as cotton, jute, flax, ramie and regenerated cellulose, wherein the form of cellulosic fibre material existence can be: fiber, yarn, woven fabrics or knitted fabrics.
Have a chloro-s-triazine base and ethene sulfuryl double active base in three components of composite active red dye of the present invention, genus warm type when being used for cellulosic fibre material dye, on dye curve and approach, they are to the avidity of fiber, dye uptake, degree of fixation, to electrolyte salt, to the laking agent bases, susceptibility to bath raio and dyeing temperature is all more approaching, outstanding dyeing synchronism and level-dyeing property are arranged between the mixture, and the depth that higher degree of fixation is arranged and give prominence to, effectively overcome the defective that is existed by reactive red 3BS and reactive orange 82 composite active red dyes, made the dyeing quality of cellulosic fibre material obtain important guarantee.
In sum, the present invention has that stable performance, solubleness are high, degree of fixation is high, the dyeing synchronism is good, good level-dyeing property, color reproducibility are good, especially dyes dark outstanding advantage, is particularly useful for dyeing and printing of cellulosic fibre materials.
Embodiment
The synthetic available well-known method of each mixture, the invention will be further described below in conjunction with embodiment, but protection scope of the present invention is not limited to this.
Embodiment 1
56g is met formula (I) dyestuff (I-3), 18g meet formula (II) dyestuff (II-1) and 28g and meet formula (III) dyestuff through mechanically mixing fully and obtain composite active red dye of the present invention, this dyestuff can be dyeing into cellulosic fibre material to get dense, the good level-dyeing property of color depth, favorable reproducibility, redness that dyefastness is good.
Embodiment 2
To contain the aqueous solution of 58g formula (I) dyestuff (I-1), drying stirs after containing the aqueous solution of 15g formula (II) dyestuff (II-3) and containing the aqueous solution of 25g formula (III) dyestuff, obtain composite active red dye of the present invention, this dyestuff can be dyeing into cellulosic fibre material to get dense, the good level-dyeing property of color depth, favorable reproducibility, redness that dyefastness is good.
Embodiment 3:
65g is met formula (I) dyestuff (I-2), 14g meet formula (II) dyestuff (II-1) and 17g and meet formula (III) dyestuff through mechanically mixing fully and obtain composite active red dye of the present invention, this dyestuff can be dyeing into cellulosic fibre material to get dense, the good level-dyeing property of color depth, favorable reproducibility, redness that dyefastness is good.
Embodiment 4
To contain the aqueous solution of 68g formula (I) dyestuff (I-2), drying stirs after containing the aqueous solution of 15g formula (II) dyestuff (II-3) and containing the aqueous solution of 16g formula (III) dyestuff, obtain composite active red dye of the present invention, this dyestuff can be dyeing into cellulosic fibre material to get dense, the good level-dyeing property of color depth, favorable reproducibility, redness that dyefastness is good.
Embodiment 5
57g is met formula (I) dyestuff (I-1), 18g meet formula (II) dyestuff (II-2) and 25g and meet formula (III) dyestuff through mechanically mixing fully and obtain composite active red dye of the present invention, this dyestuff can be dyeing into cellulosic fibre material to get dense, the good level-dyeing property of color depth, favorable reproducibility, redness that dyefastness is good.
Embodiment 6
60g is met formula (I) dyestuff (I-3), 15g meet formula (II) dyestuff (II-2) and 16g and meet formula (III) dyestuff through mechanically mixing fully and obtain composite active red dye of the present invention, this dyestuff can be dyeing into cellulosic fibre material to get dense, the good level-dyeing property of color depth, favorable reproducibility, redness that dyefastness is good.
Embodiment 7
Dyeing:
With an amount of water it is fully dissolved first by the dye mixture that embodiment 1 makes 4g, then constant volume is in the 500ml volumetric flask.Drawing the 10ml dye liquor mixes with 50ml water, then add the 4g cotton, 1.8g sodium sulfate, then be raised to 60 ℃ with 1 ℃/minute heat-up rate, keep adding 1g yellow soda ash after 30 minutes, keep again 60 ℃ of dyeing 30 minutes, take out subsequently and dyed cotton, with non-ionic cleaning agent boiling soap boiling 15 minutes, water cleaned and oven dry about 70 ℃ again, and its result compares with reactive red 3BS and obtains staining power height, good level-dyeing property, favorable reproducibility, more deepens rich and gaudy beautiful redness.
Embodiment 8
Dyeing:
With an amount of water it is fully dissolved first by the dye mixture that embodiment 3 makes 4g, then constant volume is in the 500ml volumetric flask.Drawing the 10ml dye liquor mixes with 50ml water, then add the 4g cotton, 1.8g sodium sulfate, then be raised to 60 ℃ with 1 ℃/minute heat-up rate, keep adding 1g yellow soda ash after 30 minutes, keep again 60 ℃ of dyeing 30 minutes, take out subsequently and dyed cotton, with non-ionic cleaning agent boiling soap boiling 15 minutes, water cleaned and oven dry about 70 ℃ again, and its result compares with reactive red 3BS and obtains staining power height, good level-dyeing property, favorable reproducibility, more deepens rich and gaudy beautiful redness.
Embodiment 9
Dyeing:
With an amount of water it is fully dissolved first by the dye mixture that embodiment 4 makes 4g, then constant volume is in the 500ml volumetric flask.Drawing the 10ml dye liquor mixes with 50ml water, then add the 4g cotton, 1.8g sodium sulfate, then be raised to 60 ℃ with 1 ℃/minute heat-up rate, keep adding 1g yellow soda ash after 30 minutes, keep again 60 ℃ of dyeing 30 minutes, take out subsequently and dyed cotton, with non-ionic cleaning agent boiling soap boiling 15 minutes, water cleaned and oven dry about 70 ℃ again, and its result compares with reactive red 3BS and obtains staining power height, good level-dyeing property, favorable reproducibility, more deepens rich and gaudy beautiful redness.
Embodiment 10
Dyeing:
With an amount of water it is fully dissolved first by the dye mixture that embodiment 7 makes 4g, then constant volume is in the 500ml volumetric flask.Drawing the 10ml dye liquor mixes with 50ml water, then add the 4g cotton, 1.8g sodium sulfate, then be raised to 60 ℃ with 1 ℃/minute heat-up rate, keep adding 1g yellow soda ash after 30 minutes, keep again 60 ℃ of dyeing 30 minutes, take out subsequently and dyed cotton, with non-ionic cleaning agent boiling soap boiling 15 minutes, water cleaned and oven dry about 70 ℃ again, and its result compares with reactive red 3BS and obtains staining power height, good level-dyeing property, favorable reproducibility, more deepens rich and gaudy beautiful redness.
Following table is that composite active red dye of the present invention and reactive red 3BS application indexes detect contrast:
Claims (4)
1. composite active red dye is characterized in that: meter by weight, and it forms by dyestuff is composite shown in dyestuff shown in dyestuff shown in 56-68 part structural formula (I), the 13-18 part structural formula (II) and the 15-28 part structural formula (III):
In described structural formula (I), (II), (III),
R
1For-O CH
2CH
3,-CH
2CH
3
R
2A kind of in the following formula:
M is Na.
2. composite active red dye according to claim 1, it is characterized in that: the dyestuff of described formula (I) is to be selected from following formula (I-1), (I-2) or compound (I-3):
3. composite active red dye according to claim 1, it is characterized in that: the dyestuff of described formula (II) is to be selected from following formula (II-1), (II-2) or compound (II-3):
4. the application of composite active red dye claimed in claim 1 in the printing and dyeing of polyster fibre cellulose fiber material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210488621XA CN102977632A (en) | 2012-11-27 | 2012-11-27 | Compound active red dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210488621XA CN102977632A (en) | 2012-11-27 | 2012-11-27 | Compound active red dye |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102977632A true CN102977632A (en) | 2013-03-20 |
Family
ID=47851986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210488621XA Pending CN102977632A (en) | 2012-11-27 | 2012-11-27 | Compound active red dye |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103694736A (en) * | 2013-11-26 | 2014-04-02 | 大连创达技术交易市场有限公司 | Color fixing dye |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0538872B1 (en) * | 1991-10-24 | 1998-04-01 | Sumitomo Chemical Company Limited | Monoazo compounds and method for dyeing or printing fiber materials using the same |
| EP1137716B1 (en) * | 1998-07-27 | 2003-08-20 | Ciba SC Holding AG | Reactive colorants, mixtures of reactive colorants and production and use thereof |
| CN1445295A (en) * | 2003-04-10 | 2003-10-01 | 孙德锁 | Complex ractive red dye 2 |
| CN1507474A (en) * | 2001-05-11 | 2004-06-23 | �ձ���ҩ��ʽ���� | Disazo compound, reactive dye composition, and methods of dyeing cellulose or cellulose-containing fiber |
| CN1511886A (en) * | 2002-12-27 | 2004-07-14 | 上海染料化工八厂 | Red dye composition and its preparation and use |
-
2012
- 2012-11-27 CN CN201210488621XA patent/CN102977632A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0538872B1 (en) * | 1991-10-24 | 1998-04-01 | Sumitomo Chemical Company Limited | Monoazo compounds and method for dyeing or printing fiber materials using the same |
| EP1137716B1 (en) * | 1998-07-27 | 2003-08-20 | Ciba SC Holding AG | Reactive colorants, mixtures of reactive colorants and production and use thereof |
| CN1507474A (en) * | 2001-05-11 | 2004-06-23 | �ձ���ҩ��ʽ���� | Disazo compound, reactive dye composition, and methods of dyeing cellulose or cellulose-containing fiber |
| CN1511886A (en) * | 2002-12-27 | 2004-07-14 | 上海染料化工八厂 | Red dye composition and its preparation and use |
| CN1445295A (en) * | 2003-04-10 | 2003-10-01 | 孙德锁 | Complex ractive red dye 2 |
Non-Patent Citations (1)
| Title |
|---|
| 张英菊等: "苯并二呋喃酮分散红染料的合成与研究", 《染料与染色》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103694736A (en) * | 2013-11-26 | 2014-04-02 | 大连创达技术交易市场有限公司 | Color fixing dye |
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Application publication date: 20130320 |