CN1511886A - Red dye composition and its preparation and use - Google Patents
Red dye composition and its preparation and use Download PDFInfo
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- CN1511886A CN1511886A CNA021607389A CN02160738A CN1511886A CN 1511886 A CN1511886 A CN 1511886A CN A021607389 A CNA021607389 A CN A021607389A CN 02160738 A CN02160738 A CN 02160738A CN 1511886 A CN1511886 A CN 1511886A
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Abstract
The present invention relates to red dye composition suitable for dyeing and printing cotton, wool, silk, leather, synthetic polyamide fiber and other blended fiber fabric. The composition is prepared via compounding several kinds of active dyes. The active dye composition is one kind of universal red reaction dye composition with high reaction property, bright color and excellent color fastness, and is especially suitable for middle temperature dip dyeing of cotton fiber fabric at 50-70 deg.c with great tolerance of technological conditions, good dyeing reproductivity and low cost.
Description
Technical field:
The present invention relates to be applicable to that cotton, hair, silk, leather, polymeric amide close the dyeing of fibre and other mixed fiber fabrics and a kind of orchil composition of stamp, specifically the present invention relates to a kind of red reactive dye composition and preparation thereof and application.
Background technology:
Reactive dyestuffs have lovely luster, application performance excellence, easy to use, distinguishing feature such as suitability is strong.Recent two decades comes, because the factor of the restriction economy of environmental ecology, more and more higher to the requirement of dye uptake, degree of fixation and the dyeing waste-water of reactive dyestuffs, in the patent application of reactive dyestuffs, the reactive monoazo dyestuffs kind look of single chemical structure is rare.The research and development of various countries' reactive dyestuffs new variety develop to the composition that is mixed from the homogencous dyes chemical structure, and the more single dyestuff of the tinctorial yield of the composition that is mixed and degree of fixation makes quality or application performance that new lifting arranged for high.
At blue light red (dark red) category, the disclosed so far dye composite patent of the nineties is listed below:
SUMITOMO CHEMICAL company discloses the red combination dyestuff of a kind of blue light in Japanese Patent 2000192374, it is that reactive dyestuffs by following structure are mixed and combine.
Formula 1
Formula 2
The portfolio ratio (weight ratio) that is mixed is formula 1: formula 2=70: 30～30: 70, and the more single dyestuff of the tinting power of said composition and degree of fixation is high, the dyeing colorful wastewater reduces.
Summary of the invention:
The objective of the invention is to reduce deterioration and the low drawback of dyestuff its usage economy to environmental ecology, a kind of orchil preparation of compositions and application method are provided, the tinting power of the more single dyestuff of composition after making dyestuff be mixed, degree of fixation has had raising, and the latitude to dyeing is big, and it is good that the dyeing circulation ratio well reaches colour fastness.
The present invention is achieved in that this orchil composition is mixed by one or several reactive dyestuffs of general molecular formula I and one or several reactive dyestuffs of II of meeting general structure and forms.
General formula I is:
General formula I I
Wherein:
Z＝-SO
2C
2H
4OSO
3H，-SO
2C
2H
4CL，-SO
2CH＝CH
2
Z
1=Z or-SO
3H, n=0-1, m=0-2,
X＝CL，
The weight proportion that this dye composite is formed is I: II=10～90: 90～10.
The weight proportion of reactive dye compositions is preferably I among the present invention: II=30～70: 70～30
The reactive dyestuffs of described general molecular formula I among the present invention are following several structure-activity dyestuff:
Formula III
Formula IV
Formula V
Formula VI
Formula VII
Formula VIII
Formula IX
The described reactive dyestuffs that meet general structure II are the reactive dyestuffs of following several structures:
Formula X
Formula XI
Formula XII
Orchil composition of the present invention can be Powdered, particulate solid or waterborne liquid.
The preparation method of the present composition be preparation earlier by each required single dyestuff of the combination formula that is mixed, by the requirement of the combination formula that is mixed each single dyestuff being mixed then combines.
The another kind of preparation method of the present composition is in the preparation feedback process of dyestuff, by the requirement of the combination prescription that is mixed, adjusts and control the proportioning raw materials and the condition of reaction, produces the composition of expection mixed ratio in the preparation feedback process simultaneously.
Dye composite of the present invention is used for dyeing and the stamp that cotton, hair, silk, leather, polymeric amide are closed fibre and other mixed fiber fabric.Be specially adapted to exhausting of cotton fabric and dye (dip-dye), have good tinting power, enhancing and degree of fixation.
Compared with prior art, reactive dye compositions of the present invention has following advantage: the more single dyestuff of the tinctorial yield of the present composition and degree of fixation makes quality and application performance that new lifting arranged for high.
Dye composite of the present invention be a kind of reactive high, give the dense distinctness of color depth, universal red reactive dye composition that fastness is good.Can make tone red or the blue light red stain moving to gold-tinted neatly by the adjusting of the combination prescription of being mixed.This composition is applicable to that cotton, hair, silk, leather, polymeric amide close fibre and other mixed fibre.Be applicable to various traditional dyeing methods (as dip-dye, pad dyeing and stamp etc.).The middle temperature of this dye composite particularly suitable unginned cotton fiber (50 ℃～70 ℃) exhausts and dyes, and has splendid tinting power and enhancing, very high degree of fixation.Exhaust with usual middle temperature and to dye reactive dyestuffs and compare, be used for, the dyeing accelerant consumption during deep colour dyeing is few, and the gap of dye uptake and degree of fixation is little, and is big to the latitude that exhausts the dyeing technique condition.Add inorganic salt and coloured sewage quantity that not only can obviously reduce man-hour in the effluent discharge in dyeing, and the dyeing favorable reproducibility, cost is more economically.
Embodiment:
Come more detailed description the present invention with embodiment below, these embodiment just are used for illustrating the present invention, and protection scope of the present invention is not placed restrictions on by these embodiment.
Umber is by weight in the present embodiment, and temperature unit is a centigradetemperature ℃, and parts by weight are the relation of gram to milliliter to the relation of volume parts.The molecular formula of used dyestuff or compound is all represented with the sour form of freedom.
Embodiment 1
Get above-mentioned 30 parts of formula X dyestuffs that meet 30 parts of 40 parts of formula III dyestuffs, the formula IV dyestuffs of general structure I and meet structural formula general formula I I, fully be blended into the dye composite of uniformity each other, on cotton fabric, dye or stamp with following method then, can obtain to the dense distinctness of color depth, the gold-tinted that fastness is good is red.
One. be used for contaminating (exhaust and dye)
The dip-dyeing solution prescription: 0.05 part～1 part of aforesaid combination dyestuff, 7.5～45 parts of 20% (weight) Sodium sulfate anhydrous.min(99) solution, 3.75 parts～15 parts of 20% (weight) soda ash solutions, all the other add to 150 parts for water, are made into dip-dyeing solution.
Processing step: earlier with the dyestuff water dissolution, and the adding Sodium sulfate anhydrous.min(99) is configured to dye bath.Cotton is inserted dye bath in room temperature, evenly be warming up to 60 ℃, and keep this temperature to dye 30 minutes in 15～20 minutes.Add alkaline agent (soda ash liquid) then, kept 60 ℃ of alkali more solid 30～45 minutes.Sample is dyed in taking-up, after fully washing with mobile cold water, washes 10 minutes in 95 ℃ of hot water, soap boiling 10 minutes in the neutral soap flakes liquid of 2 grams per liters again, take out then dye sample with the cold water that flows clean, dehydration, oven dry, the gold-tinted redness of dark dense distinctness, every fastness is good.
Two. be used for stamp
Stamp look sauce formulation: 4～6 parts of aforesaid combination dyestuffs, 8～12 parts in urea, 2～3 parts in sodium bicarbonate, reserve salt 0.6～1.2,40～60 parts in 5% (weight) sodium alginate sauce, all the other add to 100 parts for water, are made into printing paste.
Processing step: with urea, reserve salt with the less water dissolving after, add 5% sodium alginate paste, fully stir, slowly add the good dyestuff of dissolving, and sodium bicarbonate stirs fully and is mixed with printing paste.Pour printing paste into printing machine in the slurry dish, adjust printing machine and feed the cloth mouth, start printing machine and carry out stamp.Fabric after printed was 80～90 ℃ drying in oven 3～5 minutes, will dry fabric in steam tank in 102～105 ℃ of decatizes 5～7 minutes, wash with flowing water under the room temperature, in 50～60 ℃ of hot washes, in 98～100 ℃ the liquid of soaping, boiled 10 minutes then again, again 50～60 ℃ of hot water wash, the room temperature cold wash, oven dry promptly gets dark dense distinctness, strong good gold-tinted redness.
Embodiment 2
Get above-mentioned 10 parts of formula X dyestuffs that meet 40 parts of 50 parts of formula III dyestuffs, the formula IV dyestuffs of general structure I and meet structural formula general formula I I, fully be blended into the dye composite of uniformity each other, dip-dye and printing method with embodiment 1 dyes on cotton fabric or stamp then, must give color depth gold-tinted dense, that fastness is good red.
Embodiment 3
Get above-mentioned 40 parts of formula X dyestuffs that meet 30 parts of 30 parts of formula III dyestuffs, the formula IV dyestuffs of general structure I and meet structural formula general formula I I, fully be blended into the dye composite of uniformity each other, dip-dye and printing method with embodiment 1 dyes on cotton fabric or stamp then, must give color depth gold-tinted dense, that fastness is good red.
Embodiment 4
Get above-mentioned 60 parts of formula X dyestuffs that meet 20 parts of 20 parts of formula III dyestuffs, the formula IV dyestuffs of general structure I and meet structural formula general formula I I, fully be blended into the dye composite of uniformity each other, dip-dye and printing method with embodiment 1 dyes on cotton fabric or stamp then, must give color depth gold-tinted dense, that fastness is good red.
Embodiment 5
Get above-mentioned 70 parts of formula X dyestuffs that meet 10 parts of 20 parts of formula III dyestuffs, the formula IV dyestuffs of general structure I and meet structural formula general formula I I, fully be blended into the dye composite of uniformity each other, dip-dye and printing method with embodiment 1 dyes on cotton fabric or stamp then, must give color depth gold-tinted dense, that fastness is good red.
Embodiment 6
Get above-mentioned 90 parts of formula X dyestuffs that meet 5 parts of 5 parts of formula III dyestuffs, the formula IV dyestuffs of general structure I and meet structural formula general formula I I, fully be blended into the dye composite of uniformity each other, dip-dye and printing method with embodiment 1 dyes on cotton fabric or stamp then, must give color depth gold-tinted dense, that fastness is good red.
Embodiment 7
Get above-mentioned 50 parts of 30 parts of the formula V dyestuffs of general structure I, 20 parts of formula XI dyestuffs that meet general structure II and the formula XII dyestuffs that meet, fully be blended into the dye composite of uniformity each other, dip-dye and printing method with embodiment 1 dyes on cotton fabric or stamp then, can obtain to the dense distinctness of color depth, blue light redness that fastness is good.
Embodiment 8
1. get 0.13 mole of K acid with water dissolution and to regulate PH be 6.5～7.Under good the stirring, in half an hour, be added to 0.1 mole of cyanuric chloride by well-established law in the suspension of frozen water then, stirred 2～3 hours in 0～5 ℃ of condensation, add 0.04 mole of 2-naphthylamines-5-hydroxyl 1 again, 7 disulfonic acids and 0.03 mole of 3-β sulfuric ester ethyl sulfonyl aniline (are all used earlier water dissolution, PH is 6～6.5), carefully be warming up to 30～45 ℃ after stirring, be 4.5～6 with soda ash hydraulic control system PH, continued insulated and stirred 3～6 hours, and made condensation complete.
2. the 3-β sulfuric ester ethyl sulfonyl aniline of getting 0.17 mole in addition is by well-established law diazotization, then this diazonium liquid is added to the aforementioned two thing solution that contract and carries out coupling under 5～10 ℃, carefully controlling coupling medium with soda ash liquid is PH6～7, and continues to stir 4-8 hour in 5～15 ℃, and coupling is finished.
3. the dye liquor that above-mentioned coupling is finished is carried dense with membrane filter method (reverse osmosis membrane or sodium filter membrane) desalination, add an amount of buffering salt and dust-proofing agent again, directly carry out spraying drying then, get the dry powder dyestuff, this powder dye on cotton, dye or stamp for to the dense distinctness of color depth, gold-tinted redness that fastness is good, in mainly contain the composition of following formula VI, formula X and three kinds of dyestuffs of formula VII, their portfolio ratio that is mixed (mol ratio) is about VI: VII: X=3: 4: 3.
Embodiment 9
1. get 0.15 mole of H acid, use water dissolution, and to regulate PH be 6.5～7, in half an hour, be added in the suspension of 0.1 mole of cyanuric chloride and frozen water under good the stirring by well-established law then, in 0～5 ℃ of condensation stirring 2～3 hours.The 3-β sulfuric ester ethyl sulfonyl aniline (using water dissolution, PH earlier is 6～6.5) that adds 0.05 mole more carefully is warming up to 30～45 ℃ after stirring, with soda ash hydraulic control system PH is 4.5～6, continued insulated and stirred 3～6 hours, and made condensation complete, it is standby to be cooled to room temperature then.
2. get 0.1 mole of H acid in addition, use water dissolution, and to regulate PH be 6.5～7, in half an hour, be added in the suspension of 0.05 mole of cyanuric chloride and frozen water under good the stirring by well-established law then, in 0～5 ℃ of condensation stirring 1～2 hour.Being warming up to 30～45 ℃ again, is 4.5～6 with soda ash hydraulic control system PH, continues insulated and stirred and makes condensation complete in 3～6 hours.The 3-β sulfuric ester ethyl sulfonyl aniline (using water dissolution, PH earlier is 6～6.5) that adds 0.05 mole then, mitigation is warming up to 90～95 ℃, is 4.5～5.5 in PH, insulated and stirred 1～3 hour, the complete postcooling of condensation is standby to room temperature.
The condenses liquid (being cooled to room temperature) of above-mentioned #1 and #2 is evenly mixed 3., under 5～10 ℃ and PH6～7 conditions, carry out coupling then with the diazonium salt (by well-established law diazotization) of 0.25 mole of 4-β sulfuric ester ethyl sulfonyl aniline, stirred 4～8 hours with 5～15 ℃ of couplings, make to react completely.
4. the dye liquor that above-mentioned coupling is finished membrane filter method desalination extract, add an amount of buffering salt and dust-proofing agent etc. again and add auxiliary agent, directly carry out spraying drying then and get the dry powder slurry, dyeing or stamp are that the blue light that fastness is good is red to the dense distinctness of color depth on cotton.Mainly contain the composition of following formula VIII, IX and three kinds of dyestuffs of formula XII in this powder dye, their mixed ratio (mol ratio) is VIII: IX: XII=1: 1: 1.
Claims (7)
1. orchil composition is characterized in that: said composition is by one or several reactive dyestuffs that meet general structure I and meet one or several reactive dyestuffs of general structure II and be mixed and form.
General formula I is:
General formula I I is:
Wherein:
Z＝-SO
2C
2H
4OSO
3H，-SO
2C
2H
4CL，-SO
2CH＝CH
2
Z
1=Z or-SO
3H, n=0-1, m=0-2,
X＝CL，
The weight proportion of this dye component is I: II=10～90: 90～10.
2. orchil composition according to claim 1 is characterized in that: the weight proportion that said composition is formed is I: II=30～70: 70～30.
3. orchil composition according to claim 1 is characterized in that: the reactive dyestuffs of described general molecular formula I are the reactive dyestuffs of following several structures:
Formula III
Formula IV
Formula V
Formula VI
Formula VII
Formula VII
Formula VIII
Formula IX
The described reactive dyestuffs that meet general structure II are the reactive dyestuffs of following several structures:
Formula X
Formula XI
Formula XII
4. according to claim 1 or 2 or 3 described orchil compositions, it is characterized in that: said composition is Powdered, particulate solid or waterborne liquid.
5. orchil preparation of compositions method as claimed in claim 1 is characterized in that: preparation earlier is by each required single dyestuff of the combination formula that is mixed, and by the requirement of the combination formula that is mixed each single dyestuff being mixed then combines.
6. orchil preparation of compositions method as claimed in claim 1, it is characterized in that: in the preparation feedback process of dyestuff, requirement by the combination formula that is mixed, adjust and control the proportioning raw materials and the reaction conditions of reaction, in the preparation feedback process, produce the composition of the mixed ratio of expection simultaneously.
7. the application of an orchil composition as claimed in claim 1 is characterized in that: said composition is used for dyeing and the stamp that cotton, hair, silk, leather, polymeric amide are closed fibre and other mixed fiber fabric.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021607389A CN100404629C (en) | 2002-12-27 | 2002-12-27 | Red dye composition and its preparation and use |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021607389A CN100404629C (en) | 2002-12-27 | 2002-12-27 | Red dye composition and its preparation and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1511886A true CN1511886A (en) | 2004-07-14 |
| CN100404629C CN100404629C (en) | 2008-07-23 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB021607389A Expired - Fee Related CN100404629C (en) | 2002-12-27 | 2002-12-27 | Red dye composition and its preparation and use |
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| Country | Link |
|---|---|
| CN (1) | CN100404629C (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007026116A2 (en) * | 2005-08-31 | 2007-03-08 | Atul Limited | Reactive azo compounds |
| CN101323709B (en) * | 2007-06-11 | 2011-05-04 | 上海雅运纺织化工有限公司 | Red reactive dye composition and dyeing application thereof to fibre material |
| CN102977632A (en) * | 2012-11-27 | 2013-03-20 | 江苏德旺化工工业有限公司 | Compound active red dye |
| CN103554980A (en) * | 2013-09-29 | 2014-02-05 | 天津德凯化工股份有限公司 | Red reactive dye and preparation method thereof |
| CN103554981A (en) * | 2013-09-29 | 2014-02-05 | 天津德凯化工股份有限公司 | Red reactive dye |
| CN111019390A (en) * | 2019-12-26 | 2020-04-17 | 浙江劲光实业股份有限公司 | Preparation method of composite active bright red dye |
| CN112679981A (en) * | 2020-12-21 | 2021-04-20 | 江苏德美科化工有限公司 | High-temperature high-chlorine-resistance active red dye for cotton and preparation method thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5330539A (en) * | 1991-12-18 | 1994-07-19 | Hoechst Celanese Corporation | Fiber reactive dyes - applications with low salt |
| DE4415313A1 (en) * | 1994-05-02 | 1995-11-09 | Hoechst Ag | Mixtures of fiber-reactive dyes and their use for dyeing fiber materials |
| DE19922826A1 (en) * | 1999-05-19 | 2000-11-23 | Dystar Textilfarben Gmbh & Co | Orange and scarlet mixtures of reactive dyes |
| JP4538906B2 (en) * | 2000-06-12 | 2010-09-08 | 住友化学株式会社 | Reactive dye composition and its application to textile materials |
-
2002
- 2002-12-27 CN CNB021607389A patent/CN100404629C/en not_active Expired - Fee Related
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007026116A2 (en) * | 2005-08-31 | 2007-03-08 | Atul Limited | Reactive azo compounds |
| WO2007026116A3 (en) * | 2005-08-31 | 2007-05-18 | Atul Ltd | Reactive azo compounds |
| CN101323709B (en) * | 2007-06-11 | 2011-05-04 | 上海雅运纺织化工有限公司 | Red reactive dye composition and dyeing application thereof to fibre material |
| CN102977632A (en) * | 2012-11-27 | 2013-03-20 | 江苏德旺化工工业有限公司 | Compound active red dye |
| CN103554980A (en) * | 2013-09-29 | 2014-02-05 | 天津德凯化工股份有限公司 | Red reactive dye and preparation method thereof |
| CN103554981A (en) * | 2013-09-29 | 2014-02-05 | 天津德凯化工股份有限公司 | Red reactive dye |
| CN111019390A (en) * | 2019-12-26 | 2020-04-17 | 浙江劲光实业股份有限公司 | Preparation method of composite active bright red dye |
| CN111019390B (en) * | 2019-12-26 | 2021-02-02 | 浙江劲光实业股份有限公司 | Preparation method of composite active bright red dye |
| CN112679981A (en) * | 2020-12-21 | 2021-04-20 | 江苏德美科化工有限公司 | High-temperature high-chlorine-resistance active red dye for cotton and preparation method thereof |
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| Publication number | Publication date |
|---|---|
| CN100404629C (en) | 2008-07-23 |
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