CN104311779A - Synthetic method of water-based polyurethane high polymer dye - Google Patents
Synthetic method of water-based polyurethane high polymer dye Download PDFInfo
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- CN104311779A CN104311779A CN201410554339.6A CN201410554339A CN104311779A CN 104311779 A CN104311779 A CN 104311779A CN 201410554339 A CN201410554339 A CN 201410554339A CN 104311779 A CN104311779 A CN 104311779A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
- C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/285—Nitrogen containing compounds
- C08G18/286—Oximes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3275—Hydroxyamines containing two hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6688—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3271
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
- D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
- D06P1/5285—Polyurethanes; Polyurea; Polyguanides
Abstract
The invention discloses a synthetic method of a water-based polyurethane high polymer dye, belonging to the technical field of textile and chemical engineering. The synthetic method comprises the following steps: reacting polyisocyanate with polyhydric alcohol polymer to generate polyurethane prepolymer; extending chain by virtue of a hydrophilic chain extender to introduce the dye containing -NH2 or -OH in the parent on a polyurethane chain; and finally, adding an end-capping reagent to perform end capping on the water-based polyurethane to obtain the water-based polyurethane high polymer dye based on the dye parent. The water-based polyurethane high polymer dye disclosed by the invention not only has the advantages of high strength, easy film forming, good solvent resistance and heat resistance, easy processing, and the like of the high polymer material, but also has strong absorption on light and colorful effects of a micromolecular organic dye; and moreover, the problems of difficulty in diffusion, a complex process, and the like are solved by part dyes, so that the dye consumption is greatly lowered and the dye utilization rate is increased.
Description
Technical field
A synthetic method for aqueous polyurethane high molecular dye, belongs to technical field of textile chemical engineering.
Background technology
The normally low-molecular-weight dyestuff of pigment that fiber staining uses or pigment.Pigment need give fiber colorful property by original liquid coloring or pigment dyeing and stamp or coating process, but the friction fastness of pigment dyeing and Printing is not good enough, the dispersion stabilization of pigment and filming polymer is always not good, and tinting strength is low, also have detrimentally affect to the workability of superpolymer, the thermotolerance of part pigment also has problems.In addition, the utilization ratio of some dyestuff when dyeing is not high, easy to change during the thermal treatment of processing after dyeing, easily move.And many dyestuffs and pigment also poor to the stability of light, have impact on wearing quality and the outward appearance of related products.
High molecular dye, dye molecule introduced high molecular main chain by certain chemical reaction or hang on the coloured macromolecule polymkeric substance that side chain is formed, molecular structure is made up of macromolecular scaffold and color bodies two portions, owing to being colored dyes and colourless polymer Chemical bond, make the function such as adsorption selection of the photoabsorption of its existing dye matrix, light emission, photoconduction electricity, acid-base discoloration and enzyme, also have the stability of polymkeric substance, consistency, wholesomeness and the easy characteristic such as film-forming properties simultaneously.Such characteristic just receives the concern of people at the beginning of high molecular dye is studied, thus develops rapidly.High molecular dye is structurally adjustable simultaneously, both the structure similar to synthon can be designed, also can design the high molecular dye of multi-active base structure for natural fiber dyeing, thus during colouring synthetic fibres with contaminate the consistency and resistance to extracting power that fiber had.These advantages make high molecular dye become the substitute of research and development prohibitive dye and synthesize the focus of more high-efficiency environment friendly dyestuff.
Summary of the invention
The object of the present invention is to provide a kind of synthetic method of aqueous polyurethane high molecular dye, concrete technology is as follows: 30-42wt% polyisocyanates and 18-27wt% polyhydric alcohol polymer are instilled there-necked flask, be warming up to 80 DEG C, reaction 40min, in process, retrogradation adds 2-5wt% acetone, prepares base polyurethane prepolymer for use as; 8-14wt% hydrophilic chain extender is dissolved in 2-5wt% acetone, is dropwise added drop-wise in base polyurethane prepolymer for use as, be warming up to 80 DEG C and react 40min; 1-3wt% low molecule dyestuff is directly added in there-necked flask and reacts 2h, then add 20-30wt% end-capping reagent, and react 1h at 80 DEG C; Be cooled to 40-50 DEG C, then add in HAC and acetone and salify, after evaporating organic solvent, obtain aqueous polyurethane high molecular dye.
Described polyisocyanates is isophorone diisocyanate, Toluene-2,4-diisocyanate, 4-vulcabond, Toluene-2,4-diisocyanate, the one in 6-vulcabond, poly methylene poly phenyl poly isocyanate.
Described polyhydric alcohol polymer is the one in polyoxyethylene glycol, polypropylene glycol, two polyglycerols.
Described hydrophilic chain extender is the one in N methyldiethanol amine, dihydroxymethyl carboxylic acid, dimethylol propionic acid.
Described low molecule dyestuff is containing-NH in dye matrix structure
2or the dyestuff of-OH.
Described end-capping reagent is the one in methyl ethyl ketoxime, phenol, hexanolactam, Sodium Pyrosulfite, sodium bisulfite, ammonium bisulfite, N methyldiethanol amine.
Synthesized aqueous polyurethane high molecular dye may be used for textile coating stamp, concrete technology is: will prepare aqueous polyurethane high molecular dye and be dissolved in 60 DEG C of hot water, the weight ratio of dyestuff and water is 1: 1-1: 5, stirring and dissolving is even, leave standstill 3h, by scraper plate direct blade coating on fabric, then dry in 60 DEG C of baking ovens, obtain decalcomania.
Embodiment
To contribute to further understanding the present invention by following embodiment, but content of the present invention can not be limited.
Embodiment 1
36wt% isophorone diisocyanate and 21wt% polyoxyethylene glycol are instilled there-necked flask, is warming up to 80 DEG C, reaction 40min, in process, retrogradation adds 5wt% acetone, prepares base polyurethane prepolymer for use as; 9wt% hydrophilic chain extender N methyldiethanol amine is dissolved in 2wt% acetone, is dropwise added drop-wise in base polyurethane prepolymer for use as, be warming up to 80 DEG C and react 40min; 2wt%C.I. EX-SF DISPERSE BLUE EX-SF 300 3 is directly added in there-necked flask and reacts 2h, then add 25wt% methyl ethyl ketoxime, and react 1h at 80 DEG C; Be cooled to 50 DEG C, then add in HAC and acetone and salify, after evaporating organic solvent, obtain aqueous polyurethane high molecular dye.
The aqueous polyurethane high molecular dye of preparation is used for pigment printing of cotton fabric, concrete technology is: will prepare aqueous polyurethane high molecular dye and be dissolved in 60 DEG C of hot water, the weight ratio of dyestuff and water is 1: 2, stirring and dissolving is even, leave standstill 3h, by scraper plate direct blade coating on fabric, then dry in 60 DEG C of baking ovens, bright in color light, decalcomania that fastness is excellent can be obtained.
Embodiment 2
By 38wt% Toluene-2,4-diisocyanate, 4-vulcabond and 18wt% polypropylene glycol instill there-necked flask, are warming up to 80 DEG C, reaction 40min, and in process, retrogradation adds 4wt% acetone, prepares base polyurethane prepolymer for use as; 13wt% hydrophilic chain extender dihydroxymethyl carboxylic acid is dissolved in 3wt% acetone, is dropwise added drop-wise in base polyurethane prepolymer for use as, is warming up to 80 DEG C and reacts 40min; Directly add direct for 3wt%C.I. yellow 25 in there-necked flask and react 2h, then add 21wt% phenol, and react 1h at 80 DEG C; Be cooled to 50 DEG C, then add in HAC and acetone and salify, after evaporating organic solvent, obtain aqueous polyurethane high molecular dye.
The aqueous polyurethane high molecular dye of preparation is used for pigment printing of cotton fabric, concrete technology is: will prepare aqueous polyurethane high molecular dye and be dissolved in 60 DEG C of hot water, the weight ratio of dyestuff and water is 1: 4, stirring and dissolving is even, leave standstill 3h, by scraper plate direct blade coating on fabric, then dry in 60 DEG C of baking ovens, bright in color light, decalcomania that fastness is excellent can be obtained.
Claims (7)
1. the synthetic method of an aqueous polyurethane high molecular dye, it is characterized in that: 30-42wt% polyisocyanates and 18-27wt% polyhydric alcohol polymer are instilled there-necked flask, is warming up to 80 DEG C, reaction 40min, in process, retrogradation adds 2-5wt% acetone, prepares base polyurethane prepolymer for use as; 8-14wt% hydrophilic chain extender is dissolved in 2-5wt% acetone, is dropwise added drop-wise in base polyurethane prepolymer for use as, be warming up to 80 DEG C and react 40min; 1-3wt% low molecule dyestuff is directly added in there-necked flask and reacts 2h, then add 20-30wt% end-capping reagent, and react 1h at 80 DEG C; Be cooled to 40-50 DEG C, then add in HAC and acetone and salify, after evaporating organic solvent, obtain aqueous polyurethane high molecular dye.
2. the synthetic method of a kind of aqueous polyurethane high molecular dye as claimed in claim 1, it is characterized in that described polyisocyanates is isophorone diisocyanate, Toluene-2,4-diisocyanate, 4-vulcabond, Toluene-2,4-diisocyanate, the one in 6-vulcabond, poly methylene poly phenyl poly isocyanate.
3. the synthetic method of a kind of aqueous polyurethane high molecular dye as claimed in claim 1, is characterized in that described polyhydric alcohol polymer is the one in polyoxyethylene glycol, polypropylene glycol, two polyglycerols.
4. the synthetic method of a kind of aqueous polyurethane high molecular dye as claimed in claim 1, is characterized in that described hydrophilic chain extender is the one in N methyldiethanol amine, dihydroxymethyl carboxylic acid, dimethylol propionic acid.
5. the synthetic method of a kind of aqueous polyurethane high molecular dye as claimed in claim 1, is characterized in that described low molecule dyestuff is containing-NH in dye matrix structure
2or the dyestuff of-OH.
6. the synthetic method of a kind of aqueous polyurethane high molecular dye as claimed in claim 1, is characterized in that described end-capping reagent is the one in methyl ethyl ketoxime, phenol, hexanolactam, Sodium Pyrosulfite, sodium bisulfite, ammonium bisulfite, N methyldiethanol amine.
7. the synthetic method of a kind of aqueous polyurethane high molecular dye as claimed in claim 1, it is characterized in that synthesized aqueous polyurethane high molecular dye may be used for textile coating stamp, concrete technology is: will prepare aqueous polyurethane high molecular dye and be dissolved in 60 DEG C of hot water, the weight ratio of dyestuff and water is 1: 1-1: 5, stirring and dissolving is even, leaves standstill 3h, by scraper plate direct blade coating on fabric, then dry in 60 DEG C of baking ovens, obtain decalcomania.
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| CN201410554339.6A CN104311779B (en) | 2014-10-11 | 2014-10-11 | A kind of synthetic method of aqueous polyurethane high molecular dye |
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| CN201410554339.6A CN104311779B (en) | 2014-10-11 | 2014-10-11 | A kind of synthetic method of aqueous polyurethane high molecular dye |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105219125A (en) * | 2015-10-26 | 2016-01-06 | 江南大学 | A kind of preparation method of self-vulcanizing non-isocyanate water polyurethane base high molecular dye |
| CN106758421A (en) * | 2017-01-18 | 2017-05-31 | 江南大学 | A kind of method of the imitative tie dyeing style treatment of utilization polyurethane-base high molecular dye |
| CN108530602A (en) * | 2018-03-19 | 2018-09-14 | 安徽建筑大学 | A kind of color-changing polyurethane acrylic colour resin and preparation method |
| CN105949425B (en) * | 2016-06-07 | 2019-01-15 | 安徽建筑大学 | A kind of polyurethane black high molecular dye, preparation method and application |
| CN109467673A (en) * | 2018-09-10 | 2019-03-15 | 清华大学 | A kind of enclosed type active anion colorful polyurethane emulsion and its preparation method and application |
| CN109512700A (en) * | 2018-11-16 | 2019-03-26 | 安徽清彩科技有限公司 | A kind of copolymerization Colour nail polish and preparation method thereof |
| CN109880049A (en) * | 2019-02-26 | 2019-06-14 | 安徽清彩科技有限公司 | A kind of colored preparation method and application for covering polyaminoester emulsion of copolymerization |
| CN111849201A (en) * | 2020-07-30 | 2020-10-30 | 江苏华彩化学科技有限公司 | Macromolecular dye and application thereof in super-concentrated efficient antibacterial laundry gel bead |
| CN114250634A (en) * | 2022-01-17 | 2022-03-29 | 常熟理工学院 | Cassia seed microcapsule dye, preparation method and application thereof |
| CN114316204A (en) * | 2021-12-02 | 2022-04-12 | 盐城工学院 | Preparation method of pH color-changing textile based on Congo red-aqueous polyurethane high-molecular dye |
| CN115386061A (en) * | 2022-08-04 | 2022-11-25 | 辽宁恒星精细化工有限公司 | Heat-reactive waterborne polyurethane resin and preparation method and application thereof |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105219125A (en) * | 2015-10-26 | 2016-01-06 | 江南大学 | A kind of preparation method of self-vulcanizing non-isocyanate water polyurethane base high molecular dye |
| CN105949425B (en) * | 2016-06-07 | 2019-01-15 | 安徽建筑大学 | A kind of polyurethane black high molecular dye, preparation method and application |
| CN106758421A (en) * | 2017-01-18 | 2017-05-31 | 江南大学 | A kind of method of the imitative tie dyeing style treatment of utilization polyurethane-base high molecular dye |
| CN108530602B (en) * | 2018-03-19 | 2020-05-19 | 安徽建筑大学 | Color-changing polyurethane acrylic dye resin and preparation method thereof |
| CN108530602A (en) * | 2018-03-19 | 2018-09-14 | 安徽建筑大学 | A kind of color-changing polyurethane acrylic colour resin and preparation method |
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