CN1511884A - Bright red dye composition and its preparation and use - Google Patents
Bright red dye composition and its preparation and use Download PDFInfo
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- CN1511884A CN1511884A CNA021607397A CN02160739A CN1511884A CN 1511884 A CN1511884 A CN 1511884A CN A021607397 A CNA021607397 A CN A021607397A CN 02160739 A CN02160739 A CN 02160739A CN 1511884 A CN1511884 A CN 1511884A
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- red dye
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- large red
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- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000001044 red dye Substances 0.000 title claims abstract description 13
- 239000000975 dye Substances 0.000 claims abstract description 62
- 229920000742 Cotton Polymers 0.000 claims abstract description 16
- 238000004043 dyeing Methods 0.000 claims abstract description 16
- 239000004744 fabric Substances 0.000 claims abstract description 16
- 239000000835 fiber Substances 0.000 claims abstract description 11
- 239000010985 leather Substances 0.000 claims abstract description 5
- 239000002131 composite material Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 3
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000007639 printing Methods 0.000 abstract description 10
- 239000004952 Polyamide Substances 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- 238000013329 compounding Methods 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000985 reactive dye Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000002932 luster Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000015067 sauces Nutrition 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229940056729 sodium sulfate anhydrous Drugs 0.000 description 2
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000019846 buffering salt Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical class [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- -1 ester ethyl sulfonyl anilines Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- IQVSWLPEOQMCQD-UHFFFAOYSA-N n-phenylethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC=C1 IQVSWLPEOQMCQD-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
The present invention relates to bright red dye composition suitable for dyeing and printing cotton, wool, silk, leather, synthetic polyamide fiber and other blended fiber fabric and its preparation process and application. The composition is prepared via compounding several kinds of active dyes. The active dye composition has excellent coloring capacity, building up property and fixation rate, and is especially suitable for middle temperature dip dyeing of cotton fiber fabric at 50-70 deg.c.
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 fabric and a kind of large red dye composite of stamp, specifically the present invention relates to a kind of large red reactive dye compositions 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 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.
Reactive dye compositions at the large red category is actually rare, and German Hoechct company discloses a kind of dark orange～scarlet dye composition in U.S. USP5556435, and it is mixed by the reactive dyestuffs of following structural formula and combines.
Formula 1
Formula 2
Formula 3
Above-mentioned dye composite is based on formula 1 and formula 2, and along with the mixed ratio increase of formula 3, the color and luster of dye composite turns to large red from darkorange.
SUMITOMO CHEMICAL company discloses a kind of blue light scarlet dye composition in Japanese Patent JP2000281922, it is mixed by the reactive dyestuffs of following structural formula and combines.
Formula 4
Formula 5
Aforesaid combination dyestuff (4+5) tinctorial yield height, low during dyeing with the salt amount, dyeing condition adaptability broad.
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 preparation and application method of large red dye composite 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 large red reactive dye compositions is mixed by one or several reactive dyestuffs of general molecular formula I and one or several reactive dyestuffs of meeting general structure II and forms.
General formula I
Wherein:
Z＝-SO
2C
2H
4OSO
3H，-SO
2C
2H
4CL，-SO
2CH＝CH
2
General formula I I is
Wherein:
m＝0～1，R＝H，-CH
3，-C
2H
5
Z＝-SO
2C
2H
4OSO
3H，-SO
2C
2H
4CL，-SO
2CH＝CH
2
The weight proportion that composition is formed is I: II=20～80: 80～20.
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
The reactive dyestuffs of general molecular formula II described in the present invention are following several structure-activity dyestuff:
Formula XI
Formula X
Formula (XI)
Formula (XII)
Dye composite of the present invention can be Powdered, particulate solid, or waterborne liquid.
Preparation method of the present invention 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, dye composite of the present invention has following advantage: the present invention is mixed the tinctorial yield of composition and the more single dyestuff of degree of fixation for high, makes quality and application performance that new lifting arranged.
The present invention be a kind of reactive high, give the dense distinctness of color depth, universal large red dye composite that fastness is good, it can make tone bright red to the bright red change of blue light by gold-tinted neatly with the change of the combination formula that is mixed.This composition is applicable to that cotton, hair, silk, leather, polymeric amide close the dyeing and the stamp of fibre and other mixed fiber fabric, is applicable to various traditional dyeing methods (as dip-dye, pad dyeing and stamp etc.).The middle temperature (50 ℃～70 ℃) that this dye composite is specially adapted to cotton fibre exhausts dyes (dip-dye), have good tinting power, enhancing and degree of fixation exhaust with common middle temperature and to dye the type reactive dyestuffs and compare, latitude to the dyeing condition is big, the dyeing favorable reproducibility.
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 IX dyestuffs that meet 25 parts of 45 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 dark dense distinctness, gold-tinted that fastness is good bright red.
One. contaminate (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% 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 large red of dark dense distinctness, each fastness is good.
Two. 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, and strong good gold-tinted is bright red.
Embodiment 2
Get above-mentioned 40 parts of formula IX dyestuffs that meet 20 parts of 40 parts of formula III dyestuffs, the formula IV dyestuffs of general structure I and meet structural formula general formula I I, the fully mixed dye composite of forming, on cotton fabric, dye or stamp with dip-dye and the printing method of implementing 1 then, dark dense distinctness, gold-tinted that fastness is good are bright red.
Embodiment 3
Get above-mentioned 55 parts of formula IX dyestuffs that meet 15 parts of 30 parts of formula III dyestuffs, the formula IV dyestuffs of general structure I and meet structural formula general formula I I, the fully mixed dye composite of forming, on cotton fabric, dye or stamp with dip-dye and the printing method of implementing 1 then, must give color depth gold-tinted dense, that fastness is good bright red.
Embodiment 4
Get above-mentioned 70 parts of formula IX 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, the fully mixed dye composite of forming, on cotton fabric, dye or stamp with dip-dye and the printing method of implementing 1 then, must give look distinctness, gold-tinted that fastness is good bright red.
Embodiment 5
Get above-mentioned 25 parts of formula X dyestuffs that meet 30 parts of 45 parts of formula V dyestuffs, the formula VI 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 and stamp, must give the dense distinctness of color depth, large red that fastness is good by the method for implementing 1.
Embodiment 6
Get above-mentioned 20 parts of formula X dyestuffs that meet 45 parts of 35 parts of formula V dyestuffs, the formula VI 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 and stamp, must give the dense distinctness of color depth, blue light large red that fastness is good by the method for implementing 1.
Embodiment 7
1. get 26.5 parts of K acid and 8.5 parts of 2-naphthylamines-5-hydroxyl-1:7 disulfonic acid water dissolution, and be adjusted to PH6.5～7, and add 18.5 parts of trichlorine paracyanogen in half an hour under agitation then, stirred 2～3 hours in 0～5 ℃ of condensation, continue to stir 1～2 hour in PH3～5 again, make condensation reaction complete.
2. the 3-β sulfuric ester ethyl sulfonyl aniline of getting 28.1 parts in addition is added to this diazonium liquid then and carries out coupling in the aforementioned condensated liquid, in PH6～7 by well-established law diazotization in 5～10 ℃; 12.5～15 ℃ of couplings were stirred 4～8 hours, made condensation reaction complete.
3. in the reaction solution that above-mentioned even summation finishes, add 28.1 parts of 3-β sulfuric ester ethyl sulfonyl anilines (using earlier water dissolution, PH6～6.5), heat up 30～50 ℃ then, make condensation complete in PH4.5～6 insulated and stirred 4～6 hours.
4. the dye liquor that above-mentioned reaction is finished is carried densely with the membrane filter method desalination, adds an amount of buffering salt and dust-proofing agent etc. again and adds auxiliary agent, and directly spraying drying gets the dry powder dyestuff then.This powder dye on cotton, dye or stamp splendid for, degree of fixation dense and enhancing to color depth, the gold-tinted that every fastness is good is bright red.Be mainly the composition that contains above-mentioned formula VIII, two kinds of dyestuffs of formula XII, the portfolio ratio between them (mol ratio) is about XII: VIII=3: 1.
Claims (7)
1. large red dye composite is characterized in that: said composition is mixed by one or several reactive dyestuffs that meet general structure I and one or several reactive dyestuffs of meeting general structure II and forms.
General formula I is
Wherein:
?n＝1～2
Z＝-SO
2C
2H
4OSO
3H，-SO
2C
2H
4CL，-SO
2CH＝CH
2
General formula I I is
Wherein:
m＝0～1，R＝H，-CH
3，-C
2H
5
Z=-SO
2C
2H
4OSO
3H ,-SO
2C
2H
4CL ,-SO
2CH=CH
2The weight proportion that composition is formed is I: II=20～80: 80～20.
2. large red dye composite according to claim 1 is characterized in that: the weight proportion that said composition is formed is I: II=30～70: 70～30.
3. large red dye composite according to claim 1 is characterized in that: the reactive dyestuffs of described general molecular formula I are following several structure-activity dyestuff:
Formula III
Formula IV
Formula V
Formula VI
Formula VII
Formula VIII
The reactive dyestuffs of described general molecular formula II are following several structure-activity dyestuff:
Formula IX
Formula X
Formula XI
Formula XII
4. according to claim 1 or 2 or 3 described large red dye composites, it is characterized in that: said composition is Powdered, particulate solid or waterborne liquid.
5. the preparation method of a large red dye composite 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. the preparation method of a large red dye composite 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 mixed ratio composition of expection simultaneously.
7. the application of a large red dye composite 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 |
|---|---|---|---|
| CNB021607397A CN100404628C (en) | 2002-12-27 | 2002-12-27 | Bright red dye composition and its preparation and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021607397A CN100404628C (en) | 2002-12-27 | 2002-12-27 | Bright red dye composition and its preparation and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1511884A true CN1511884A (en) | 2004-07-14 |
| CN100404628C CN100404628C (en) | 2008-07-23 |
Family
ID=34237975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB021607397A Expired - Fee Related CN100404628C (en) | 2002-12-27 | 2002-12-27 | Bright red dye composition and its preparation and use |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100404628C (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102558905A (en) * | 2011-12-09 | 2012-07-11 | 浙江吉华集团有限公司 | Composite reactive red dye for low-salt dyeing and dyeing application thereof |
| CN101565560B (en) * | 2009-04-14 | 2012-10-17 | 丽源(湖北)科技有限公司 | Red reactive dye mixture and preparation and application thereof |
| CN104774484A (en) * | 2014-12-29 | 2015-07-15 | 浙江科永化工有限公司 | Reactive red dye composition |
| CN105273440A (en) * | 2014-05-26 | 2016-01-27 | 湖北丽源科技股份有限公司 | Red reactive dye mixture |
| CN105985664A (en) * | 2015-03-05 | 2016-10-05 | 湖北丽源科技股份有限公司 | Red fluorine-containing reactive dye mixture and application thereof |
| CN108148446A (en) * | 2016-12-05 | 2018-06-12 | 湖北丽源科技股份有限公司 | A kind of red reactive dye mixture and its application |
| CN111320882A (en) * | 2018-12-14 | 2020-06-23 | 湖北丽源科技股份有限公司 | A kind of bright red reactive dye mixture and its preparation method and application |
| CN115594991A (en) * | 2022-10-09 | 2023-01-13 | 浙江亿得新材料股份有限公司（Cn） | High washing fastness compound type active bright red dye |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4841032A (en) * | 1986-09-19 | 1989-06-20 | Sumitomo Chemical Company, Limited | Fiber reactive monoazo compounds having two vinylsulfone type fiber reactive groups in the molecule |
| JP3198635B2 (en) * | 1992-06-26 | 2001-08-13 | 住友化学工業株式会社 | Reactive dye mixture and dyeing or printing method using the same |
| DE4415313A1 (en) * | 1994-05-02 | 1995-11-09 | Hoechst Ag | Mixtures of fiber-reactive dyes and their use for dyeing fiber materials |
| DE19836661A1 (en) * | 1998-08-13 | 2000-02-17 | Dystar Textilfarben Gmbh & Co | Dye mixture of water-soluble fiber-reactive azo dyes, process for their preparation and their use |
| US6090163A (en) * | 1998-12-21 | 2000-07-18 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Red-dyeing dye mixtures of water-soluble fiber-reactive azo dyes and their use |
-
2002
- 2002-12-27 CN CNB021607397A patent/CN100404628C/en not_active Expired - Fee Related
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101565560B (en) * | 2009-04-14 | 2012-10-17 | 丽源(湖北)科技有限公司 | Red reactive dye mixture and preparation and application thereof |
| CN102558905A (en) * | 2011-12-09 | 2012-07-11 | 浙江吉华集团有限公司 | Composite reactive red dye for low-salt dyeing and dyeing application thereof |
| CN105273440A (en) * | 2014-05-26 | 2016-01-27 | 湖北丽源科技股份有限公司 | Red reactive dye mixture |
| CN105273440B (en) * | 2014-05-26 | 2017-02-08 | 湖北丽源科技股份有限公司 | Red reactive dye mixture |
| CN104774484A (en) * | 2014-12-29 | 2015-07-15 | 浙江科永化工有限公司 | Reactive red dye composition |
| CN104774484B (en) * | 2014-12-29 | 2017-02-22 | 浙江科永化工有限公司 | Reactive red dye composition |
| CN105985664A (en) * | 2015-03-05 | 2016-10-05 | 湖北丽源科技股份有限公司 | Red fluorine-containing reactive dye mixture and application thereof |
| CN108148446A (en) * | 2016-12-05 | 2018-06-12 | 湖北丽源科技股份有限公司 | A kind of red reactive dye mixture and its application |
| CN111320882A (en) * | 2018-12-14 | 2020-06-23 | 湖北丽源科技股份有限公司 | A kind of bright red reactive dye mixture and its preparation method and application |
| CN111320882B (en) * | 2018-12-14 | 2021-07-30 | 湖北丽源科技股份有限公司 | A kind of bright red reactive dye mixture and its preparation method and application |
| CN115594991A (en) * | 2022-10-09 | 2023-01-13 | 浙江亿得新材料股份有限公司（Cn） | High washing fastness compound type active bright red dye |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100404628C (en) | 2008-07-23 |
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