CN101962491A - Ecotypic reactive disperse dye and preparation method and application thereof - Google Patents

Ecotypic reactive disperse dye and preparation method and application thereof Download PDF

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CN101962491A
CN101962491A CN2010105057012A CN201010505701A CN101962491A CN 101962491 A CN101962491 A CN 101962491A CN 2010105057012 A CN2010105057012 A CN 2010105057012A CN 201010505701 A CN201010505701 A CN 201010505701A CN 101962491 A CN101962491 A CN 101962491A
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disperse
red
blue
disperse blue
vio
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何瑾馨
董霞
张宾
宣建
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Donghua University
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Donghua University
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Abstract

The invention relates to an ecotypic reactive disperse dye and a preparation method and application thereof. The dye is a product obtained by connecting the amino-group-containing disperse dye and the hydroxyl-containing disperse dye with amino terminated polyether or hydroxyl terminated polyether by taking a group, such as triazine ring, and the like, as a bridge group. The preparation method comprises the following steps of: connecting the amino terminated polyether or the hydroxyl terminated polyether with groups, such as s-triazine group, and the like; and then reacting the group with the disperse dye to obtain the ecotypic reactive disperse dye. The ecotypic reactive disperse dye can be taken not only as a reactive dye for dyeing a cotton fiber or a fabric, but also as the temporary soluble disperse dye for dyeing a polyester fiber or the fabric, and also as a dispersing agent for preparing a self-disperse dye. The ecotypic reactive disperse dye has the advantages of simple preparation method, high conversion rate and easy industrialization.

Description

A kind of environmental reactive disperse dyes and preparation method thereof and application
Technical field
The invention belongs to dispersed dye and preparation thereof and Application Areas, particularly relate to a kind of environmental reactive disperse dyes and preparation method thereof and application.
Background technology
Dispersed dye are as a kind of common water-insoluble dyestuff, have a wide range of applications in dyeing terylene, field such as ink-jet printed.Because dispersed dye are the extremely low nonionic state of solubleness in water, can be dispersed in preferably in the solution in order to make dyestuff, dye granule must be ground to below the 2 μ m outside, also need add a large amount of dispersion agents in the process of lapping.But traditional dispersion agent is because the limitation or the structural defective of manufacturing technology, causes its quality instability, dispersive ability poor, and is very big for preventing that the dispersed dye flocculation from needing to add the amount of dispersion agent.At present, the dispersion agent that the commodity dispersed dye contain is at least more than 50%, other auxiliary agent that adds when adding dyeing, the ratio of dyestuff and auxiliary agent even reach more than 1: 2 in the dye bath.Just because of this, there are technical barriers such as dyeing waste-water COD value is high, dye utilization rate is low, dyeing behavior is not enough, water loss is big in dispersed dye when practical application.
Summary of the invention
Technical problem to be solved by this invention provides a kind of environmental reactive disperse dyes and preparation method thereof and application, prepared reactive disperse dyes can be used as the dispersion agent of preparation dispersed dye, it is a kind of reactive dyestuffs, it also is a kind of temporary soluble disperse dye, can be directly used in fiber or coloration of textile materials such as cotton, terylene, its preparation method is simple, and transformation efficiency is higher, industrialization easily.
A kind of environmental reactive disperse dyes of the present invention, general structure is:
Dye-B-E
Wherein, Dye is the dispersed dye molecule that contains amino, hydroxy functional group; B is
Figure BDA0000028090460000011
Figure BDA0000028090460000012
E is for having active polyoxyethylene of water-wetted surface and/or polyoxypropylene segment.
The described amino that contains, the dispersed dye molecule of hydroxy functional group is the C.I. disperse red 60, C.I. DISPERSE YELLOW 6, C.I. DISPERSE YELLOW 9, C.I. DISPERSE YELLOW 11, C.I. DISPERSE ORANGE 30 200 3, C.I. DISPERSE ORANGE 30 200 11, C.I. Disperse Red 4, C.I. dispersion red 11, C.I. Red-1 200 5, C.I. Disperse Red 31, C.I. Disperse Red 53, C.I. Disperse Red 55, C.I. Disperse Red 59, C.I. Disperse Red 63, C.I. Disperse Red 70, C.I. Disperse Red 75, C.I. disperse red 86, C.I. disperse red 91, C.I. Disperse Red 92, C.I. Red-1 200 21, C.I. Red-1 200 22, C.I. Red-1 200 27, C.I. DISPERSE Red 13 2, C.I. Red-1 200 46, C.I. Red-1 200 65, C.I. Red-1 200 64, C.I. Red-1 200 89, C.I. Red-1 200 90, C.I. disperse red 191, C.I. Red-1 200 92, C.I. Disperse Red 207, C.I. Disperse Red 288, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 1, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 4, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 6, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 8, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 15, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 17, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 26, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 28, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 31, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 35, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 36, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 38, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 46, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 51, C.I. EX-SF DISPERSE BLUE EX-SF 300 1, C.I. EX-SF DISPERSE BLUE EX-SF 300 5, C.I. EX-SF DISPERSE BLUE EX-SF 300 6, C.I. EX-SF DISPERSE BLUE EX-SF 300 9, C.I. EX-SF DISPERSE BLUE EX-SF 300 11, C.I. disperse Blue 19, C.I. EX-SF DISPERSE BLUE EX-SF 300 20, C.I. EX-SF DISPERSE BLUE EX-SF 300 28, C.I. EX-SF DISPERSE BLUE EX-SF 300 31, C.I. EX-SF DISPERSE BLUE EX-SF 300 35, C.I. EX-SF DISPERSE BLUE EX-SF 300 40, C.I. EX-SF DISPERSE BLUE EX-SF 300 54, C.I. Disperse Blue-56, C.I. EX-SF DISPERSE BLUE EX-SF 300 58, C.I. Disperse Blue-60, C.I. EX-SF DISPERSE BLUE EX-SF 300 62, C.I. EX-SF DISPERSE BLUE EX-SF 300 73, C.I. EX-SF DISPERSE BLUE EX-SF 300 81, C.I. EX-SF DISPERSE BLUE EX-SF 300 83, C.I. EX-SF DISPERSE BLUE EX-SF 300 87, C.I. EX-SF DISPERSE BLUE EX-SF 300 91, C.I. EX-SF DISPERSE BLUE EX-SF 300 95, C.I. EX-SF DISPERSE BLUE EX-SF 300 99, C.I. EX-SF DISPERSE BLUE EX-SF 300 104, C.I. EX-SF DISPERSE BLUE EX-SF 300 103, C.I. EX-SF DISPERSE BLUE EX-SF 300 105, C.I. EX-SF DISPERSE BLUE EX-SF 300 108, C.I. EX-SF DISPERSE BLUE EX-SF 300 113, C.I. EX-SF DISPERSE BLUE EX-SF 300 143, C.I. EX-SF DISPERSE BLUE EX-SF 300 144, C.I. EX-SF DISPERSE BLUE EX-SF 300 158, C.I. EX-SF DISPERSE BLUE EX-SF 300 167, C.I. EX-SF DISPERSE BLUE EX-SF 300 175, C.I. EX-SF DISPERSE BLUE EX-SF 300 176, C.I. EX-SF DISPERSE BLUE EX-SF 300 181, C.I. EX-SF DISPERSE BLUE EX-SF 300 185, C.I. disperse Blue 19 7, C.I. disperse Blue 19 8, C.I. Disperse Blue 214, C.I. EX-SF DISPERSE BLUE EX-SF 300 297, C.I. EX-SF DISPERSE BLUE EX-SF 300 327, C.I. disperse black 1, C.I. disperse black 2, C.I. disperse black 3, C.I. disperse black 4, C.I. disperse black 6, C.I. disperse black 7, C.I. disperse black 9, C.I. disperse black 10, C.I. disperse black 26, C.I. disperse black 27, C.I. disperse black 28, C.I. dispersion black 29 or C.I. disperse black 30.
The structure of described polyoxyethylene and/or polyoxypropylene segment is
(1)-NH(CH(CH 3)CH 2O) x(CH 2CH 2O) yR 1
0≤x<1000,8≤y<1000 wherein, R 1Be alkyl;
(2)-O(CH(CH 3)CH 2O) m(CH 2CH 2O) nR 2
0<m<1000,8≤n≤1000 wherein, R 2Be alkyl;
Molecular weight is 300~10 6, total adduct number of polyoxypropylene is 0~1 with the ratio of polyoxyethylated total adduct number.
The preparation method of a kind of environmental reactive disperse dyes of the present invention, comprise: polyethers is dissolved in the anhydrous solvent that comprises siccative, acid binding agent, back adding and the equimolar nitrogen-containing heterocycle compound of polyethers stir under the room temperature, room temperature condition is reaction 12~48h down, and then adding and the equimolar dispersed dye that contain amino, hydroxyl of polyethers, at 40~50 ℃ of reaction 20~30h, temperature rising reflux reaction 2~6h again; Filter, behind the rotary evaporation solvent, promptly get the ecologic active dispersed dye.Described polyether structure is
(1)H 2N(CH(CH 3)CH 2O) x(CH 2CH 2O) yR 1
0≤x<1000,8≤y<1000 wherein, R 1Be alkyl;
(2)HO(CH(CH 3)CH 2O) m(CH 2CH 2O) nR 2
0<m<1000,8≤n≤1000 wherein, R 2Be alkyl;
The hydrophile-lipophile balance value HLB of polyethers is 10~24, and molecular weight is 300~10 6, total adduct number of polyoxypropylene is 0~1 with the ratio of polyoxyethylated total adduct number.
Described siccative is molecular sieve or anhydrous magnesium sulfate, with the mass ratio of polyethers be 1: 0.2~2.
Described acid binding agent is anhydrous sodium carbonate or sodium hydroxide, with the mass ratio of polyethers be 1: 0.2~2.
Described anhydrous solvent is toluene, benzene, acetone, acetonitrile, dioxane, tetrahydrofuran (THF), chloroform or tetracol phenixin, with the mass ratio of polyethers be 1: 0.01~1.
Described nitrogen-containing heterocycle compound is cyanuric chloride, cyanuric fluoride, tetrachloro-pyrimidine, trifluoro one chloropyrimide or 2-methylsulfonyl dichloromethyl pyrimidine.
A kind of environmental reactive disperse dyes of the present invention is used for cotton fibre or textile dyeing, is used for polyster fibre or textile dyeing or is used to prepare the dispersion agent of self-dispersing dye as soluble disperse dye temporarily as reactive dyestuffs.
Preparation method of the present invention, the polyethers that at first will contain end amino or terminal hydroxy group connects groups such as going up s-triazine, and then reaction makes environmental reactive disperse dyes with dispersed dye.
Hydrolysis can take place in this product in fiber such as terylene or fabric high temperature dyeing process, dye matrix on the dispersed dye that hydrolysis generates can continue, thereby the utilization ratio of dispersed dye is improved, and reduces the discharging of colorful wastewater, and the COD of dye bath CrBe worth lower.Simultaneously, it is a kind of reactive dyestuffs, also is a kind of temporary soluble disperse dye, can be directly used in fiber or coloration of textile materials such as cotton, terylene.
Beneficial effect
(1) the prepared reactive disperse dyes of the present invention can be used as the dispersion agent of preparation dispersed dye, and it is a kind of reactive dyestuffs, also is a kind of temporary soluble disperse dye, can be directly used in fiber or coloration of textile materials such as cotton, terylene;
(2) preparation method is simple, and transformation efficiency is higher, industrialization easily.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in and limit the scope of the invention.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Embodiment 1
With 2.0g (2mmol)
Figure BDA0000028090460000031
(provided by HUNTSMAN company, structural formula is CH 3-[OCH 2CH 2] y-[OCH 2CH (CH 3)] x-NH 2Y/x is about 19/3, and HLB is 17.0, and molecular weight is about 1000), 5g molecular sieve, 5g anhydrous sodium carbonate and 30mL dry toluene join in the 250mL round-bottomed flask, vigorous stirring 1~3h under the room temperature, add again and contain 0.369g cyanuric chloride (about 2mmol, 99%), react 48h under the stirring at room, add 0.66g C.I. disperse red 60 (about 2mmol again, 99%), is heated to 40~50 ℃ of reaction 30h, then temperature rising reflux reaction 4h.Reaction finishes after-filtration and removes insolubless such as molecular sieve, anhydrous sodium carbonate, and the rotary evaporation solvent obtains product, and yield is greater than 80%.
Embodiment 2
(provided by Cognis company, structural formula is with 7.44g (2mmol) Agnique NP 4030
Figure BDA0000028090460000041
Molecular weight is about 3720), 5g molecular sieve, 5g anhydrous sodium carbonate and 30mL dry toluene join in the 250mL round-bottomed flask, vigorous stirring 1~3h under the room temperature, add 0.369g cyanuric chloride (about 2mmol, 99%) then, under the stirring at room reaction 48h after, add 0.66g C.I. disperse red 60 (about 2mmol, 99%), is heated to 40~50 ℃ of reaction 30h, then temperature rising reflux reaction 6h.Reaction finishes after-filtration and removes insolubless such as molecular sieve, anhydrous sodium carbonate, and the rotary evaporation solvent obtains product, and yield is greater than 80%.
Embodiment 3
With 4.0g (2mmol)
Figure BDA0000028090460000042
(provided by HUNTSMAN company, structural formula is CH 3-[OCH 2CH 2] y-[OCH 2CH (CH 3)] x-NH 2Y/x is about 33/10, and HLB is 13.8, and molecular weight is about 2000), 5g molecular sieve, 5g anhydrous sodium carbonate and 30mL dry toluene join in the 250mL round-bottomed flask, vigorous stirring 2h under the room temperature, add again and contain 0.369g cyanuric chloride (about 2mmol, 99%), react 48h under the stirring at room, add 0.72g C.I. EX-SF DISPERSE BLUE EX-SF 300 73 (about 2mmol again, 99%), is heated to 40~50 ℃ of reaction 30h, then temperature rising reflux reaction 4h.Reaction finishes after-filtration and removes insolubless such as molecular sieve, anhydrous sodium carbonate, and the rotary evaporation solvent obtains product, and yield is greater than 75%.

Claims (10)

1. environmental reactive disperse dyes, general structure is:
Dye-B-E
Wherein, Dye is the dispersed dye molecule that contains amino, hydroxy functional group; B is
Figure FDA0000028090450000011
Figure FDA0000028090450000012
E is for having active polyoxyethylene of water-wetted surface and/or polyoxypropylene segment.
2. a kind of environmental reactive disperse dyes according to claim 1 is characterized in that: the described amino that contains, the dispersed dye molecule of hydroxy functional group is the C.I. disperse red 60, C.I. DISPERSE YELLOW 6, C.I. DISPERSE YELLOW 9, C.I. DISPERSE YELLOW 11, C.I. DISPERSE ORANGE 30 200 3, C.I. DISPERSE ORANGE 30 200 11, C.I. Disperse Red 4, C.I. dispersion red 11, C.I. Red-1 200 5, C.I. Disperse Red 31, C.I. Disperse Red 53, C.I. Disperse Red 55, C.I. Disperse Red 59, C.I. Disperse Red 63, C.I. Disperse Red 70, C.I. Disperse Red 75, C.I. disperse red 86, C.I. disperse red 91, C.I. Disperse Red 92, C.I. Red-1 200 21, C.I. Red-1 200 22, C.I. Red-1 200 27, C.I. DISPERSE Red 13 2, C.I. Red-1 200 46, C.I. Red-1 200 65, C.I. Red-1 200 64, C.I. Red-1 200 89, C.I. Red-1 200 90, C.I. disperse red 191, C.I. Red-1 200 92, C.I. Disperse Red 207, C.I. Disperse Red 288, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 1, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 4, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 6, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 8, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 15, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 17, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 26, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 28, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 31, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 35, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 36, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 38, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 46, C.I. 63 ,DIS,PER,SE ,Vio,let, 63 51, C.I. EX-SF DISPERSE BLUE EX-SF 300 1, C.I. EX-SF DISPERSE BLUE EX-SF 300 5, C.I. EX-SF DISPERSE BLUE EX-SF 300 6, C.I. EX-SF DISPERSE BLUE EX-SF 300 9, C.I. EX-SF DISPERSE BLUE EX-SF 300 11, C.I. disperse Blue 19, C.I. EX-SF DISPERSE BLUE EX-SF 300 20, C.I. EX-SF DISPERSE BLUE EX-SF 300 28, C.I. EX-SF DISPERSE BLUE EX-SF 300 31, C.I. EX-SF DISPERSE BLUE EX-SF 300 35, C.I. EX-SF DISPERSE BLUE EX-SF 300 40, C.I. EX-SF DISPERSE BLUE EX-SF 300 54, C.I. Disperse Blue-56, C.I. EX-SF DISPERSE BLUE EX-SF 300 58, C.I. Disperse Blue-60, C.I. EX-SF DISPERSE BLUE EX-SF 300 62, C.I. EX-SF DISPERSE BLUE EX-SF 300 73, C.I. EX-SF DISPERSE BLUE EX-SF 300 81, C.I. EX-SF DISPERSE BLUE EX-SF 300 83, C.I. EX-SF DISPERSE BLUE EX-SF 300 87, C.I. EX-SF DISPERSE BLUE EX-SF 300 91, C.I. EX-SF DISPERSE BLUE EX-SF 300 95, C.I. EX-SF DISPERSE BLUE EX-SF 300 99, C.I. EX-SF DISPERSE BLUE EX-SF 300 104, C.I. EX-SF DISPERSE BLUE EX-SF 300 103, C.I. EX-SF DISPERSE BLUE EX-SF 300 105, C.I. EX-SF DISPERSE BLUE EX-SF 300 108, C.I. EX-SF DISPERSE BLUE EX-SF 300 113, C.I. EX-SF DISPERSE BLUE EX-SF 300 143, C.I. EX-SF DISPERSE BLUE EX-SF 300 144, C.I. EX-SF DISPERSE BLUE EX-SF 300 158, C.I. EX-SF DISPERSE BLUE EX-SF 300 167, C.I. EX-SF DISPERSE BLUE EX-SF 300 175, C.I. EX-SF DISPERSE BLUE EX-SF 300 176, C.I. EX-SF DISPERSE BLUE EX-SF 300 181, C.I. EX-SF DISPERSE BLUE EX-SF 300 185, C.I. disperse Blue 19 7, C.I. disperse Blue 19 8, C.I. Disperse Blue 214, C.I. EX-SF DISPERSE BLUE EX-SF 300 297, C.I. EX-SF DISPERSE BLUE EX-SF 300 327, C.I. disperse black 1, C.I. disperse black 2, C.I. disperse black 3, C.I. disperse black 4, C.I. disperse black 6, C.I. disperse black 7, C.I. disperse black 9, C.I. disperse black 10, C.I. disperse black 26, C.I. disperse black 27, C.I. disperse black 28, C.I. dispersion black 29 or C.I. disperse black 30.
3. a kind of environmental reactive disperse dyes according to claim 1 is characterized in that: the structure of described polyoxyethylene and/or polyoxypropylene segment is
(1)-NH(CH(CH 3)CH 2O) x(CH 2CH 2O) yR 1
0≤x<1000,8≤y<1000 wherein, R 1Be alkyl;
(2)-O(CH(CH 3)CH 2O) m(CH 2CH 2O) nR 2
0<m<1000,8≤n≤1000 wherein, R 2Be alkyl;
Molecular weight is 300~10 6, total adduct number of polyoxypropylene is 0~1 with the ratio of polyoxyethylated total adduct number.
4. the preparation method of an environmental reactive disperse dyes, comprise: polyethers is dissolved in the anhydrous solvent that comprises siccative, acid binding agent, back adding and the equimolar nitrogen-containing heterocycle compound of polyethers stir under the room temperature, room temperature condition is reaction 12~48h down, and then adding and the equimolar dispersed dye that contain amino, hydroxyl of polyethers, at 40~50 ℃ of reaction 20~30h, temperature rising reflux reaction 2~6h again; Filter, behind the rotary evaporation solvent, promptly get the ecologic active dispersed dye.
5. the preparation method of a kind of environmental reactive disperse dyes according to claim 4, it is characterized in that: described polyether structure is
(1)H 2N(CH(CH 3)CH 2O) x(CH 2CH 2O) yR 1
0≤x<1000,8≤y<1000 wherein, R 1Be alkyl;
(2)HO(CH(CH 3)CH 2O) m(CH 2CH 2O) nR 2
0<m<1000,8≤n≤1000 wherein, R 2Be alkyl;
The hydrophile-lipophile balance value HLB of polyethers is 10~24, and molecular weight is 300~10 6, total adduct number of polyoxypropylene is 0~1 with the ratio of polyoxyethylated total adduct number.
6. the preparation method of a kind of environmental reactive disperse dyes according to claim 4, it is characterized in that: described siccative is molecular sieve or anhydrous magnesium sulfate, with the mass ratio of polyethers be 1: 0.2~2.
7. the preparation method of a kind of environmental reactive disperse dyes according to claim 4, it is characterized in that: described acid binding agent is anhydrous sodium carbonate or sodium hydroxide, with the mass ratio of polyethers be 1: 0.2~2.
8. the preparation method of a kind of environmental reactive disperse dyes according to claim 4, it is characterized in that: described anhydrous solvent is toluene, benzene, acetone, acetonitrile, dioxane, tetrahydrofuran (THF), chloroform or tetracol phenixin, with the mass ratio of polyethers be 1: 0.01~1.
9. the preparation method of a kind of environmental reactive disperse dyes according to claim 4 is characterized in that: described nitrogen-containing heterocycle compound 3 is cyanuric chloride, cyanuric fluoride, tetrachloro-pyrimidine, trifluoro one chloropyrimide or 2-methylsulfonyl dichloromethyl pyrimidine.
10. an environmental reactive disperse dyes is used for cotton fibre or textile dyeing, is used for polyster fibre or textile dyeing or is used to prepare the dispersion agent of self-dispersing dye as soluble disperse dye temporarily as reactive dyestuffs.
CN2010105057012A 2010-10-13 2010-10-13 Ecotypic reactive disperse dye and preparation method and application thereof Pending CN101962491A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107057401A (en) * 2017-04-21 2017-08-18 苏州大学 Dichloro s-triazine type reactive disperse dyes based on anthraquinone and preparation method thereof
CN109970965A (en) * 2019-04-19 2019-07-05 北京材华科技有限公司 A kind of preparation method of gradient color macromolecular dyestuff

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101195716A (en) * 2007-11-23 2008-06-11 东华大学 Production method of self-dispersing dye
CN101294006A (en) * 2008-06-18 2008-10-29 东华大学 Process for synthesizing pH sensitive disperse dye polyether derivative

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101195716A (en) * 2007-11-23 2008-06-11 东华大学 Production method of self-dispersing dye
CN101294006A (en) * 2008-06-18 2008-10-29 东华大学 Process for synthesizing pH sensitive disperse dye polyether derivative

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107057401A (en) * 2017-04-21 2017-08-18 苏州大学 Dichloro s-triazine type reactive disperse dyes based on anthraquinone and preparation method thereof
CN107057401B (en) * 2017-04-21 2019-03-15 苏州大学 Dichloro s-triazine type reactive disperse dyes based on anthraquinone and preparation method thereof
CN109970965A (en) * 2019-04-19 2019-07-05 北京材华科技有限公司 A kind of preparation method of gradient color macromolecular dyestuff

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Application publication date: 20110202