CN111662405A - Preparation method of self-adhesive polymer/disperse dye composite particle and application of self-adhesive polymer/disperse dye composite particle in polyester hot-melt dyeing - Google Patents
Preparation method of self-adhesive polymer/disperse dye composite particle and application of self-adhesive polymer/disperse dye composite particle in polyester hot-melt dyeing Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/20—Aqueous medium with the aid of macromolecular dispersing agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F218/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/02—Esters of monocarboxylic acids
- C08F218/04—Vinyl esters
- C08F218/08—Vinyl acetate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
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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
- D06P1/16—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 dispersed, e.g. acetate, dyestuffs
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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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
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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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/20—Physical treatments affecting dyeing, e.g. ultrasonic or electric
- D06P5/2066—Thermic treatments of textile materials
- D06P5/2077—Thermic treatments of textile materials after dyeing
Abstract
The invention discloses a preparation method of self-adhesive polymer/disperse dye composite particles and application of the self-adhesive polymer/disperse dye composite particles in polyester hot-melt dyeing. The preparation method comprises the following steps: (1) mixing disperse dye, a dispersing agent, a defoaming agent and water, and grinding the disperse dye into particles with the size of 100-1000 nm to form aqueous dispersion of disperse dye particles; (2) dissolving an emulsifier and a dispersant in water to obtain an aqueous phase solution; mixing a vinyl monomer and a co-stabilizer to obtain an oil phase solution; mixing the water phase solution and the oil phase solution to prepare a monomer micro-suspension; (3) and mixing the dispersed dye particle water dispersion liquid with the monomer micro-suspension, shearing to obtain the monomer micro-suspension containing the dispersed dye, and polymerizing to prepare the self-adhesive polymer/dispersed dye composite particles. The self-adhesive polymer/disperse dye composite particle prepared by the invention has good water dispersibility and strong adhesion to polyester fiber, is applied to hot-melt dyeing processing of polyester, and can improve the dyeing efficiency and dyeing effect of disperse dye.
Description
(I) technical field
The invention relates to a preparation method of polymer/disperse dye composite particles and application of the polymer/disperse dye composite particles in polyester hot-melt dyeing.
(II) background of the invention
The disperse dye is coated by the high molecular material, so that the surface property of the disperse dye is changed, and the water dispersibility and the application performance of the disperse dye can be improved [ Coloration Technology,2010,121,76-80 ]; journal of applied Polymer Science,2011,121, 1616-. At present, composite particles composed of disperse dyes and polymers are applied to high-temperature and high-pressure dyeing processing of terylene, and in order to adapt to a dyeing process, the polymers with high temperature resistance, difficult softening, hardness and mechanical strength are generally selected as materials for coating the disperse dyes.
The hot melt dyeing is a continuous polyester dyeing processing technology, has the advantages of energy saving and less water compared with polyester high-temperature and high-pressure dyeing, and is more in line with the trend of green sustainable development of the industry. The hot-melt dyeing requires that disperse dyes are quickly transferred from a dye bath to the surface of fibers in a padding mode and quickly diffused into the fibers to finish dyeing in a subsequent hot-melt color fixing stage. The acting force of the polymer/disperse dye composite particles with rigid shell walls and fibers is weak, the transfer efficiency from a dye bath to the fiber surface is low, and the requirements of polyester hot-melt dyeing processing are difficult to meet. Therefore, there is a need to design and develop novel polymer/disperse dye composite particles suitable for hot melt dyeing processing according to the characteristics of the polyester hot melt dyeing process.
The invention is based on the water-based micro-suspension polymerization technology, realizes the in-situ and efficient coating of the viscous polymer on the disperse dye particles through the free radical polymerization of the vinyl monomer in the monomer liquid drop, prepares the self-adhesive polymer/disperse dye composite particles with good water dispersibility and strong adhesion to polyester fibers, and applies the polymer/disperse dye composite particles to the hot-melt dyeing processing of the polyester, thereby improving the dyeing efficiency and dyeing effect of the disperse dye.
Disclosure of the invention
The first object of the present invention is to provide a method for preparing self-adhesive polymer/disperse dye composite particles.
It is a second object of the present invention to provide self-adhesive polymer/disperse dye composite particles.
The third purpose of the invention is to provide the application of the self-adhesive polymer/disperse dye composite particles in the polyester fabric hot-melt dyeing process.
In order to achieve the purpose, the invention adopts the technical scheme that:
in a first aspect, the present invention provides a method for preparing self-adhesive polymer/disperse dye composite particles, the method comprising the steps of:
(1) mixing disperse dye, dispersant, defoamer and water, adding the mixture into a grinding device, and grinding the disperse dye into particles with the size of 100-1000 nm under the action of grinding beads to form aqueous dispersion of the disperse dye particles, wherein the mass consumption of the disperse dye is 2-40% of the mass consumption of the water used in the step, the mass consumption of the dispersant is 0.05-15% of the mass consumption of the water used in the step, and the mass consumption of the defoamer is 0.01-0.5% of the mass consumption of the water used in the step;
the dispersant is selected from at least one of the following: polyacrylic acid and its salts, polyvinyl alcohol, polymethacrylic acid and its salts, sodium lignosulfonate, maleic anhydride-styrene copolymer, methylcellulose, hydroxypropyl cellulose, hydroxypropyl methylcellulose, gelatin, and sodium alginate;
the defoaming agent is selected from at least one of the following: polyoxyethylene polyoxypropylene pentaerythritol ether, polyoxyethylene polyoxypropylene amine ether, polyoxypropylene glycerol ether, polyoxypropylene polyoxyethylene glycerol ether, and polydimethylsiloxane;
(2) dissolving an emulsifier and a dispersant in water to obtain an aqueous phase solution; mixing a vinyl monomer and a co-stabilizer to obtain an oil phase solution; mixing the water phase solution and the oil phase solution, and then carrying out high-speed shearing at 2000-20000 rpm for 0.5-90 min to obtain a monomer micro-suspension; wherein the mass usage of water is 80-1700% of the total mass usage of vinyl monomers (hydrophobic vinyl monomers and polar vinyl monomers), the mass usage of an emulsifier is 0-10% (preferably 0.1-10%) of the mass usage of water used in the step, the mass usage of a dispersant is 0.1-11% of the mass usage of water used in the step, the vinyl monomers consist of hydrophobic vinyl monomers and polar vinyl monomers, wherein the mass usage of the hydrophobic vinyl monomers is 70-99.5% of the total mass usage of the vinyl monomers, the mass usage of the polar vinyl monomers is 0.5-30% of the total mass usage of the vinyl monomers, and the mass usage of a co-stabilizer is 1-12% of the total mass usage of the vinyl monomers;
the emulsifier is selected from at least one of the following: tween series emulsifier, OP series emulsifier, MOA series emulsifier, alkyl sulfonate emulsifier, alkyl benzene sulfonate emulsifier, alkyl sulfate emulsifier, alkyl trimethyl ammonium halide emulsifier, betaine emulsifier;
the dispersant is selected from at least one of the following: polyvinyl alcohol and its derivatives, polyacrylate, polymethacrylate, sodium lignosulfonate, maleic anhydride-styrene copolymer, methylcellulose, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl methylcellulose, gelatin, sodium alginate;
the hydrophobic vinyl monomer is selected from at least one of the following: acrylate or methacrylate monomer shown in formula (I), vinyl acetate and styrene;
in the formula (I), R1Is H or CH3；R2Is a fatty straight chain or branched chain alkyl of C1-C20;
the polar vinyl monomer is selected from at least one of the following: hydroxyalkyl methacrylate, hydroxyalkyl acrylate, acrylamide, N-hydroxyalkyl acrylamide, methacrylic acid, acrylic acid, dimethylaminoethyl methacrylate, glycidyl acrylate, glycidyl methacrylate;
the co-stabilizer is selected from at least one of the following: aliphatic straight chain or branched chain alkane of C14-C22, aliphatic alcohol of C14-C22;
(3) mixing the dispersed dye particle water dispersion liquid obtained in the step (1) with the monomer micro-suspension liquid obtained in the step (2), and performing high-speed shearing treatment at 1000-18000 rpm for 0.5-200 min to obtain a monomer micro-suspension liquid containing a dispersed dye, wherein the mixing ratio of the dispersed dye particle water dispersion liquid to the monomer micro-suspension liquid is that the mass amount of the dispersed dye accounts for 10-900% of the total mass amount of vinyl monomers (hydrophobic vinyl monomers and polar vinyl monomers); after nitrogen is introduced and oxygen is removed, the temperature is adjusted to 50-90 ℃, and the mixture reacts for 0.5-24 h under the protection of nitrogen, so as to prepare self-adhesive polymer/disperse dye composite particles;
and the initiator is introduced by the following means a or b:
in the step (2), adding an oil-soluble initiator into the oil phase solution, wherein the mass usage of the oil-soluble initiator is 0.05-5% of the total mass usage of the vinyl monomer;
mode b: in the step (3), a water-soluble initiator is added to the monomer micro-suspension containing the disperse dye, wherein the mass usage of the water-soluble initiator is 0.05-5% of the total mass usage of the vinyl monomer.
In step (1) of the present invention, the grinding beads may be selected from at least one of: the grinding device comprises glass beads, stainless steel beads and zirconia beads, wherein the size of grinding beads is 0.8-2.5 mm, the rotating speed of a pump of the grinding device is 200-1800 rpm, and the grinding time is 0.5-48 h. The grinding beads are preferably zirconia beads, and the size is preferably 0.8mm to 1.2mm, in view of the grinding effect of the disperse dye.
In step (1) of the present invention, the disperse dye may be one or a combination of more of anthraquinone, azo, and heterocyclic disperse dyes. The anthraquinone disperse dye can be disperse red 60, disperse red 86, disperse red 90, disperse red 159, disperse red 210, disperse red 305, disperse red 307, disperse blue 14, disperse blue 56, disperse blue 60, disperse blue 73, disperse blue 77, disperse blue 165: 1. at least one of disperse blue 316, disperse blue 337, disperse violet 26; the azo-based disperse dye may be at least one of disperse red 50, disperse red 73, disperse red 88, disperse red 154, disperse red 177, disperse red 179, disperse red 181, disperse red 224, disperse red 343, disperse orange 25, disperse orange 29, disperse orange 30, disperse orange 44, disperse orange 61, disperse orange 73, disperse orange 288, disperse blue 79, disperse blue 82, disperse blue 106, disperse blue 183, disperse blue 284, disperse blue 291, disperse blue 295, disperse violet 48, disperse violet 52, disperse violet 63, disperse violet 93, and disperse brown 19; the heterocyclic disperse dye may be at least one of disperse red 338, disperse red 339, disperse red 340, disperse red 356, disperse yellow 54, disperse yellow 79, disperse yellow 85, disperse yellow 103, disperse yellow 114, disperse yellow 119, disperse yellow 126, disperse yellow 165, disperse yellow 211, disperse yellow 231, disperse blue 96, disperse blue 148, disperse blue 335, disperse blue 338 and disperse blue 367. The disperse dye is preferably at least one of disperse red 307, disperse yellow 211, disperse blue 337, disperse blue 338, disperse yellow 231, disperse red 356 in view of dyeing properties and good sublimation fastness.
In the step (2), the tween series emulsifier can be one or a combination of more of tween-20, tween-40, tween-60 or tween-80; the OP series emulsifier can be one or a combination of more than one of OP-7, OP-10, OP-15 or OP-20; the MOA series emulsifier can be one or a combination of more of MOA-3, MOA-7 and MOA-9. Preferably, the water-soluble nonionic emulsifier is at least one of Tween-20, OP-10 and MOA-9.
The alkyl sulfonate emulsifier may be R3-SO3M, wherein R3Is a fatty chain of C12-C20, M is Na+Or K+(ii) a The alkylbenzene sulfonate emulsifier may be R4-C6H4-SO3M, wherein R4Is a fatty chain of C10-C18, M is Na+Or K+(ii) a The alkyl trimethyl ammonium halide emulsifier may be R5N+(CH3)3X-Wherein R is5Is a C12-C20 fatty chain, and X is Cl and Br; the betaine emulsifier may be a carboxylic betaine (R)6N+(CH3)2CH2COO-Wherein R is6Fatty chain of C12-C18), sulfobetaine (R)7N+(CH3)2CH2CH2SO3 -Or R7N+(CH3)2CH2CH2CH2SO3 -Wherein R is6And R7Fatty chain of C12-C18). Preferably, the water-soluble ionic emulsifier is at least one of sodium dodecyl sulfate, cetyl trimethyl ammonium bromide and dodecyl dimethyl sulfopropyl betaine.
In step (2) of the present invention, considering the colloidal stability and the hot-melt dyeing effect of the polymer/disperse dye composite particles, the hydrophobic vinyl monomer is preferably at least one of the following: isooctyl acrylate, butyl acrylate, methyl methacrylate, vinyl acetate, styrene. The polar vinyl group is preferably at least one of: 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, methacrylic acid, acrylic acid, glycidyl methacrylate, glycidyl acrylate, N-methylolacrylamide, N-hydroxyethylacrylamide.
In step (2) of the present invention, the co-stabilizer is preferably an aliphatic linear or branched alkane having C16 to C22, more preferably n-hexadecane, in view of the stability of the droplets.
In step (2) of the present invention, the oil-soluble initiator is selected from at least one of: azobisisobutyronitrile, azobisisovaleronitrile, azobisisoheptonitrile.
In step (3) of the present invention, the water-soluble initiator is selected from at least one of the following: 2, 2' -azobisbutylamidine dihydrochloride, azobiscyanovaleric acid.
In step (3) of the present invention, the polymerization reaction temperature is preferably 55 to 75 ℃ in view of the initiation temperature of the initiator; the reaction time is preferably 1 to 24 hours.
In the present invention, it is difficult to uniformly disperse the disperse dye in water due to the hydrophobic characteristic of the disperse dye, and therefore, it is necessary to assist the milling of the dye by adding a certain amount of dispersant to achieve a desired particle diameter and obtain a uniformly dispersed aqueous dispersion of dye particles. In the grinding process, the defoaming agent is added to reduce the generation of foams and improve the grinding effect. The ball mill is adopted to grind and disperse the disperse dye, the grinding effect mainly depends on the rotating speed of the ball mill and the specification of grinding beads, and the grinding effect is better when the rotating speed is higher under the condition allowed by equipment. The size of the grinding beads also has a certain influence on the grinding effect, and if the grinding beads are smaller, the contact points between the grinding beads are more, so that the grinding effect is better. However, if the grinding beads are too small, a large amount of heat is generated, so that the temperature rises too fast to promote agglomeration, and difficulty is brought to separation of the grinding beads from the slurry.
Although the disperse dye has hydrophobicity, when the disperse dye is directly dispersed in the monomer solution, the viscosity of the monomer dispersion of the disperse dye is obviously increased along with the increase of the content of the disperse dye, and the stability of a subsequent micro-suspension polymerization system is greatly influenced. Therefore, the monomer micro-suspension is prepared, mixed with the aqueous dispersion of the disperse dye and subjected to secondary high-speed shearing to prepare the monomer micro-suspension containing the disperse dye. Researches show that the dispersant, the emulsifier and the co-stabilizer are compounded for use to generate a synergistic stabilizing effect, so that the stability of a reaction system can be improved, and the size of a product can be effectively controlled. The particle size and amount of the disperse dye can affect the coating effect of the viscous polymer, and generally, as the particle size decreases, the amount increases, and the coating rate increases. In addition, the interaction between the polymer/disperse dye composite particles and the fibers can be improved by introducing a certain amount of polar vinyl monomers, the transfer efficiency of the composite particles from a dye bath to the surfaces of the fibers is improved, and the adhesion fastness of the polymer/disperse dye composite particles on the surfaces of fabrics is enhanced.
In a second aspect, the present invention provides a self-adhesive polymer/disperse dye composite particle prepared by the above preparation method.
The preparation method of the self-adhesive polymer/disperse dye composite particle is based on an aqueous micro-suspension polymerization technology, and can realize in-situ and efficient coating of disperse dye particles by a viscous polymer through free radical polymerization of a vinyl monomer in a monomer liquid drop to prepare the self-adhesive polymer/disperse dye composite particle with good water dispersibility and strong adhesion to polyester fibers, wherein the composite particle is formed by compounding the viscous polymer and the disperse dye particles with the size of 100-1000 nm, more particularly, the polymer coats the disperse dye particles in a coating layer mode, namely the structure of the composite particle is formed by the disperse dye particles and the polymer coating layer.
In a third aspect, the invention provides an application of the self-adhesive polymer/disperse dye composite particle in polyester hot-melt dyeing.
Preferably, the application specifically comprises: self-adhesive polymer/disperse dye composite particles are prepared into the composite particles with the concentration of 20 g.L-1～80g·L-1The polyester fabric is mixed with the dye bath, and is subjected to padding to obtain the polyester fabric with the mangle ratio of 30-85 percent, the polyester fabric is placed at the temperature of 70-120 ℃ for pre-drying for 5-10 min, then is subjected to high-temperature baking and color fixing for 1-5 min at the temperature of 170-230 ℃, and the finished product of the polyester yarn-dyed fabric is obtained after the temperature is reduced to below 50 ℃.
The concentration of the padding dye liquor is preferably 35 g.L in consideration of the effect of hot melt dyeing-1～60g·L-1(ii) a MangleThe rate is preferably 40-70%; the pre-drying temperature is preferably 80-120 ℃; the high-temperature baking temperature is preferably 180-220 ℃.
Compared with the prior art, the invention has the following beneficial effects:
(1) the preparation method of the self-adhesive polymer/disperse dye composite particle has the advantages that:
the effective composition of the viscous polymer and the disperse dye particles is realized, the water dispersibility of the disperse dye is improved, and the interaction strength of the disperse dye and fibers is enhanced;
secondly, different types of self-adhesive polymer/disperse dye composite particles can be conveniently prepared through formula design of disperse dye types, monomer combinations and the like;
thirdly, the water-based production process is green, environment-friendly, simple, convenient and efficient;
(2) according to the self-adhesive polymer/disperse dye composite particle, the viscous polymer is compounded (particularly compounded in a coating form) on the disperse dye particles, so that the water dispersibility of the disperse dye is improved, the interaction strength of the disperse dye and fibers is increased, and the dyeing efficiency and the dyeing effect of the dye are improved;
(3) the self-adhesive polymer/disperse dye composite particle prepared by the invention is used as a colorant for polyester hot-melt dyeing processing, does not need to change the existing dyeing processing technology and add dyeing equipment, has good compatibility and has good dyeing effect.
(IV) detailed description of the preferred embodiments
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
example 1:
2.3g of disperse red 307 filter cake, 1.2g of sodium lignosulfonate, 0.2g of polyoxyethylene polyoxypropylene pentaerythritol ether and 50g of water were weighed out, mixed and then put into a horizontal sand mill (SWS series, Shanghai Shich electromechanical devices, Ltd.) for grinding. The grinding is carried out for 10h by adopting zirconia beads with the diameter of 0.8mm and the rotating speed of a pump of 500rpm to obtain the water dispersion liquid of the disperse dye particles.
The Z-average particle size of the disperse dye particles was 225nm as measured by a Nano-ZS90 Zetasizer dynamic light scattering nanometer particle sizer.
Dissolving 0.2g of tween-20 and 1.2g of sodium lignin sulfonate in 50g of water to obtain an aqueous phase solution; an oil phase solution was obtained by mixing 7.9g of isooctyl acrylate, 3.7g of styrene, 0.9g of 2-hydroxyethyl methacrylate, 0.9g of glycidyl acrylate, 0.9g of n-hexadecane and 0.17g of azobisisobutyronitrile, respectively. And mixing the water phase solution and the oil phase solution, and then carrying out high-speed shearing dispersion treatment for 40min under the condition of 6300rpm to prepare the monomer micro-suspension.
And mixing the disperse dye particle water dispersion with the monomer micro-suspension, and carrying out high-speed shearing dispersion treatment for 30min under the condition of 14000rpm to prepare the monomer micro-suspension containing the disperse dye. And after nitrogen is introduced to remove oxygen, adjusting the reaction temperature to 70 ℃, and reacting for 12 hours under the protection of nitrogen to obtain the self-adhesive polymer/disperse dye composite particles.
D of the self-adhesive Polymer/disperse dye composite particles was measured with a Mastersizer2000 laser particle sizer50The particle size is 3.1 +/-0.2 mu m.
The prepared self-adhesive polymer/disperse dye composite particles are prepared into 50 g.L-1And then mixing the polyester fabric with the padding dye liquor, carrying out secondary soaking and secondary rolling at room temperature to obtain the polyester fabric with the padding liquor rate of 40%, pre-drying the polyester fabric at 80 ℃ for 6min, then baking and fixing at 190 ℃ for 1.5min, and cooling to room temperature to obtain the finished product of the polyester yarn-dyed fabric.
Carrying out a rubbing color fastness test on a Model 670 manual dry-wet rubbing color fastness instrument according to GB/T3920-2008, wherein the rubbing color fastness of the sample is 4-5 grade; and (4) carrying out soaping color fastness test according to GB/T3921-2008, wherein the soaping color fastness of the sample is 4-5 grade. Testing K/S value on an UltraScan XE computer color measuring and matching instrument under the test condition of D65The samples were folded into 4 layers with 10 ° viewing angle from the light source and tested 10 times, and the K/S value of the sample was 10.594 by taking the average value.
Example 2:
4.4g of disperse yellow 211 filter cake, 3.0g of hydroxypropyl cellulose, 0.2g of polyoxyethylene polyoxypropylene ether and 60g of water were weighed out, mixed and then put into a horizontal sand mill (SWS series, Shanghai Shich electromechanical devices Co., Ltd.) for grinding. The grinding is carried out for 12h by adopting zirconia beads with the diameter of 0.8mm and the rotating speed of a pump of 400rpm, thus obtaining the water dispersion of the disperse dye particles.
The Z-average particle size of the disperse dye particles was 370nm as measured by a Nano-ZS90 Zetasizer dynamic light scattering nanometer particle sizer.
Dissolving 0.6g of MOA-9 and 3.0g of hydroxypropyl cellulose in 60g of water to obtain an aqueous phase solution; 6.9g of isooctyl acrylate, 6g of methyl methacrylate, 4.1g of vinyl acetate, 2.5g of 2-hydroxyethyl methacrylate, 0.5g of glycidyl methacrylate, 0.7g of n-hexadecane and 0.33g of azobisisoheptonitrile were weighed and mixed to obtain an oil phase solution. And mixing the water phase solution and the oil phase solution, and then carrying out high-speed shearing dispersion treatment for 30min at 6000rpm to obtain the monomer micro-suspension.
And (3) mixing the dispersed dye particle water dispersion with the monomer micro-suspension, and carrying out high-speed shearing dispersion treatment for 25min under the condition of 13000rpm to obtain the monomer micro-suspension containing the dispersed dye. And after nitrogen is introduced and oxygen is removed, adjusting the reaction temperature to 65 ℃, and reacting for 10 hours under the protection of nitrogen to obtain the self-adhesive polymer/disperse dye composite particles.
D of the self-adhesive Polymer/disperse dye composite particles was measured with a Mastersizer2000 laser particle sizer50The particle size is 3.6 +/-0.1 mu m.
The prepared self-adhesive polymer/disperse dye composite particles are prepared into 60 g.L-1And then mixing the polyester fabric with the padding dye liquor, carrying out secondary soaking and secondary rolling at room temperature to obtain the polyester fabric with the padding liquor rate of 40%, pre-drying the polyester fabric at 70 ℃ for 6min, then baking and fixing at 200 ℃ for 1.0min, and cooling to room temperature to obtain the finished product of the polyester yarn-dyed fabric.
The polyester yarn dyed fabric has the rubbing color fastness of 4-5 level, the soaping color fastness of 4-5 level and the K/S value of 10.523.
Example 3:
5.9g of disperse blue 337 filter cake, 4.5g of polyacrylic acid, 0.2g of polyoxypropylene glycerol ether and 55g of water were weighed out, mixed and then put into a horizontal sand mill (SWS series, Shanghai Shich electromechanical devices Co., Ltd.) for grinding. The grinding is carried out for 15h by adopting zirconia beads with the diameter of 1.3mm and the rotating speed of a pump of 600rpm, thus obtaining the water dispersion liquid of the disperse dye particles.
The Z-average particle size of the disperse dye particles is 385nm measured by a Nano-ZS90 Zetasizer dynamic light scattering nanometer particle sizer.
Dissolving 1.3g of dodecyl dimethyl sulfopropyl betaine and 4.5g of polyacrylic acid in 55g of water to obtain an aqueous phase solution; 8.7g of methyl methacrylate, 4.3g of methyl acrylate, 12.1g of butyl acrylate, 3.7g of 2-hydroxyethyl methacrylate, 1.6g of glycidyl acrylate and 1.3g of n-hexadecane were weighed and mixed to obtain an oil phase solution. And mixing the water phase solution and the oil phase solution, and then carrying out high-speed shearing dispersion treatment for 15min under the condition of 4000rpm to prepare the monomer micro-suspension.
And mixing the disperse dye particle water dispersion with the monomer micro-suspension, and carrying out high-speed shearing dispersion treatment for 30min under the condition of 10000rpm to prepare the monomer micro-suspension containing the disperse dye. Adding 0.42g of azodicyano valeric acid into the monomer suspension of the disperse dye, introducing nitrogen to remove oxygen, adjusting the reaction temperature to 65 ℃, and reacting for 8 hours under the protection of nitrogen to obtain the self-adhesive polymer/disperse dye composite particles.
D of the self-adhesive Polymer/disperse dye composite particles was measured with a Mastersizer2000 laser particle sizer50The particle size is 2.5 +/-0.1 mu m.
The prepared self-adhesive polymer/disperse dye composite particles are prepared into 60 g.L-1And then mixing the polyester fabric with the padding dye liquor, carrying out secondary soaking and secondary rolling at room temperature to obtain the polyester fabric with the padding liquor rate of 50%, pre-drying the polyester fabric at 70 ℃ for 8min, then baking and fixing at 210 ℃ for 2.0min, and cooling to room temperature to obtain the finished product of the polyester yarn-dyed fabric.
The polyester yarn dyed fabric has the rubbing color fastness of 4 grade, the soaping color fastness of 4 grade and the K/S value of 10.538.
Example 4:
9.3g of disperse blue 338 filter cake, 5.4g of methylcellulose, 0.2g of polyoxyethylene polyoxypropylene pentaerythritol ether and 52.5g of water were weighed out, mixed and then put into a horizontal sand mill (SWS series, Shanghai Shih electromechanical devices Co., Ltd.) for grinding. The grinding is carried out for 20h by adopting zirconia beads with the diameter of 1.5mm and the rotating speed of a pump of 600rpm, thus obtaining the water dispersion liquid of the disperse dye particles.
The Z-average particle size of the disperse dye particles was measured to be 420nm using a Nano-ZS90 Zetasizer dynamic light scattering nanometer particle sizer.
Dissolving 0.9g of sodium dodecyl sulfate and 5.4g of methylcellulose in 52.5g of water to obtain an aqueous phase solution; 13.6g of butyl acrylate, 10.1g of methyl methacrylate, 11.5g of vinyl acetate, 1.9g of acrylic acid, 1.2g of 2-hydroxyethyl acrylate, 0.37g of azobisisobutyronitrile and 0.8g of n-hexadecane were weighed and mixed to obtain an oil phase solution. And mixing the water phase solution and the oil phase solution, and then carrying out high-speed shearing dispersion treatment for 55min under the condition of 5500rpm to prepare the monomer micro-suspension.
And mixing the disperse dye particle water dispersion with the monomer micro-suspension, and carrying out high-speed shearing dispersion treatment for 20min under the condition of 12500rpm to obtain the monomer micro-suspension containing the disperse dye. And after nitrogen is introduced to remove oxygen, adjusting the reaction temperature to 68 ℃, and reacting for 6 hours under the protection of nitrogen to obtain the self-adhesive polymer/disperse dye composite particles.
D of the self-adhesive Polymer/disperse dye composite particles was measured with a Mastersizer2000 laser particle sizer50The particle size is 2.8 +/-0.1 mu m.
The prepared self-adhesive polymer/disperse dye composite particles are prepared into 75 g.L-1And then mixing the polyester fabric with the padding dye liquor, carrying out secondary soaking and secondary rolling at room temperature to obtain the polyester fabric with the padding liquor rate of 50%, placing the polyester fabric at 100 ℃ for pre-drying for 2min, then carrying out baking fixation at 190 ℃ for 2.0min, and cooling to room temperature to obtain the finished product of the polyester yarn-dyed fabric.
The polyester yarn dyed fabric has the rubbing color fastness of 4-5 level, the soaping color fastness of 4-5 level and the K/S value of 12.102.
Example 5:
14.4g of disperse yellow 231 filter cake, 6.7g of hydroxymethyl cellulose, 0.2g of polyoxypropylene glycerol ether and 47.5g of water were weighed out, mixed and then put into a horizontal sand mill (SWS series, Shanghai Shich electromechanical device Co., Ltd.) for grinding. The grinding is carried out for 24h by adopting zirconia beads with the diameter of 1.8mm and the rotating speed of a pump is 500rpm, thus obtaining the water dispersion liquid of the disperse dye particles.
The Z-average particle size of the disperse dye particles was 550nm as measured by a Nano-ZS90 Zetasizer dynamic light scattering nanometer particle sizer.
Dissolving 1.5g of OP-10 and 4.5g of hydroxymethyl cellulose in 47.5g of water to obtain an aqueous phase solution; 18.4g of vinyl acetate, 10.6g of methyl methacrylate, 22g of isooctyl acrylate, 4g N-hydroxymethyl acrylamide, 1.4g of methacrylic acid, 0.18g of azobisisobutyronitrile and 3.4g of n-hexadecane were weighed and mixed to obtain an oil phase solution. And mixing the water phase solution and the oil phase solution, and then carrying out high-speed shearing dispersion treatment for 35min under the condition of 5000rpm to prepare the monomer micro-suspension.
And mixing the disperse dye particle water dispersion with the monomer micro-suspension, and carrying out high-speed shearing dispersion treatment for 10min under the condition of 12000rpm to prepare the monomer micro-suspension containing the disperse dye. And after nitrogen is introduced to remove oxygen, adjusting the reaction temperature to 70 ℃, and reacting for 22 hours under the protection of nitrogen to obtain the self-adhesive polymer/disperse dye composite particles.
D of the self-adhesive Polymer/disperse dye composite particles was measured with a Mastersizer2000 laser particle sizer50The particle size is 1.9 +/-0.2 mu m.
The prepared self-adhesive polymer/disperse dye composite particles are prepared into 50 g.L-1And then mixing the polyester fabric with the padding dye liquor, carrying out secondary soaking and secondary rolling at room temperature to obtain the polyester fabric with the padding liquor rate of 60%, pre-drying the polyester fabric at 90 ℃ for 2.5min, then baking and fixing at 195 ℃ for 3.0min, and cooling to room temperature to obtain the finished product of the polyester yarn-dyed fabric.
The polyester yarn dyed fabric has the rubbing color fastness of 4-5 level, the soaping color fastness of 4-5 level and the K/S value of 11.315.
Example 6:
16.3g of the dispersed red 356 filter cake, 7g of sodium lignosulfonate, 0.2g of polydimethylsiloxane and 50g of water were weighed out separately, mixed and then put into a horizontal sand mill (SWS series, Shanghai Shich electromechanical devices Co., Ltd.) for grinding. The grinding is carried out for 10h by adopting zirconia beads with the diameter of 0.8mm and the rotating speed of a pump machine of 800rpm, so as to obtain the water dispersion liquid of the disperse dye particles.
The Z-average particle diameter of the disperse dye particles is 630nm measured by a Nano-ZS90 Zetasizer dynamic light scattering nanometer particle size instrument.
Dissolving 1.2g of hexadecyl trimethyl ammonium bromide and 4.5g of sodium lignin sulfonate in 50g of water to obtain an aqueous phase solution; 16.7g of methyl methacrylate, 21.7g of butyl acrylate, 10g of methyl acrylate, 1.3g of 2-hydroxyethyl methacrylate, 0.7g N-hydroxyethyl acrylamide and 2.7g of n-hexadecane were weighed and mixed to obtain an oil phase solution. Mixing the water phase solution and the oil phase solution, and performing high-speed shearing dispersion treatment for 30min at 3800rpm to obtain monomer micro-suspension.
And mixing the dispersed dye particle water dispersion liquid with the monomer micro-suspension, and carrying out high-speed shearing dispersion treatment for 15min under the condition of 8200rpm to prepare the monomer micro-suspension containing the dispersed dye. Adding 0.42g of 2, 2' -azobisbutylamidine dihydrochloride into the monomer suspension of the disperse dye, introducing nitrogen to remove oxygen, adjusting the reaction temperature to 70 ℃, and reacting for 20 hours under the protection of nitrogen to prepare the self-adhesive polymer/disperse dye composite particles.
D of the self-adhesive Polymer/disperse dye composite particles was measured with a Mastersizer2000 laser particle sizer50The particle size is 2.2 +/-0.1 mu m.
The prepared self-adhesive polymer/disperse dye composite particles are prepared into 50 g.L-1And then mixing the polyester fabric with the padding dye liquor, carrying out secondary soaking and secondary rolling at room temperature to obtain the polyester fabric with the padding liquor rate of 60%, pre-drying the polyester fabric at 80 ℃ for 5min, then baking and fixing at 190 ℃ for 4.0min, and cooling to room temperature to obtain the finished product of the polyester yarn-dyed fabric.
The polyester yarn dyed fabric has the rubbing color fastness of 4 grade, the soaping color fastness of 4 grade and the K/S value of 16.258.
The above-described embodiments of the invention are intended to be illustrative of the invention and are not to be construed as limiting the invention, and any variations that fall within the meaning and scope of the invention equivalent to the claims are intended to be embraced therein.
Claims (10)
1. A method for preparing self-adhesive polymer/disperse dye composite particles, the method comprising the steps of:
(1) mixing disperse dye, dispersant, defoamer and water, adding the mixture into a grinding device, and grinding the disperse dye into particles with the size of 100-1000 nm under the action of grinding beads to form aqueous dispersion of the disperse dye particles, wherein the mass consumption of the disperse dye is 2-40% of the mass consumption of the water used in the step, the mass consumption of the dispersant is 0.05-15% of the mass consumption of the water used in the step, and the mass consumption of the defoamer is 0.01-0.5% of the mass consumption of the water used in the step;
the dispersant is selected from at least one of the following: polyacrylic acid and its salts, polyvinyl alcohol, polymethacrylic acid and its salts, sodium lignosulfonate, maleic anhydride-styrene copolymer, methylcellulose, hydroxypropyl cellulose, hydroxypropyl methylcellulose, gelatin, and sodium alginate;
the defoaming agent is selected from at least one of the following: polyoxyethylene polyoxypropylene pentaerythritol ether, polyoxyethylene polyoxypropylene amine ether, polyoxypropylene glycerol ether, polyoxypropylene polyoxyethylene glycerol ether, and polydimethylsiloxane;
(2) dissolving an emulsifier and a dispersant in water to obtain an aqueous phase solution; mixing a vinyl monomer and a co-stabilizer to obtain an oil phase solution; mixing the water phase solution and the oil phase solution, and then carrying out high-speed shearing at 2000-20000 rpm for 0.5-90 min to obtain a monomer micro-suspension; the vinyl monomer consists of a hydrophobic vinyl monomer and a polar vinyl monomer, wherein the mass usage of the hydrophobic vinyl monomer is 70-99.5% of the total mass usage of the vinyl monomer, the mass usage of the polar vinyl monomer is 0.5-30% of the total mass usage of the vinyl monomer, the mass usage of the co-stabilizer is 1-12% of the total mass usage of the vinyl monomer, the mass usage of water is 80-1700% of the total mass usage of the vinyl monomer, the mass usage of the emulsifier is 0-10% of the mass usage of water used in the step, and the mass usage of the dispersant is 0.1-11% of the mass usage of water used in the step;
the emulsifier is selected from at least one of the following: tween series emulsifier, OP series emulsifier, MOA series emulsifier, alkyl sulfonate emulsifier, alkyl benzene sulfonate emulsifier, alkyl sulfate emulsifier, alkyl trimethyl ammonium halide emulsifier, betaine emulsifier;
the dispersant is selected from at least one of the following: polyvinyl alcohol and its derivatives, polyacrylate, polymethacrylate, sodium lignosulfonate, maleic anhydride-styrene copolymer, methylcellulose, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl methylcellulose, gelatin, sodium alginate;
the hydrophobic vinyl monomer is selected from at least one of the following: acrylate or methacrylate monomer shown in formula (I), vinyl acetate and styrene;
in the formula (I), R1Is H or CH3；R2Is a fatty straight chain or branched chain alkyl of C1-C20;
the polar vinyl monomer is selected from at least one of the following: hydroxyalkyl methacrylate, hydroxyalkyl acrylate, acrylamide, N-hydroxyalkyl acrylamide, methacrylic acid, acrylic acid, dimethylaminoethyl methacrylate, glycidyl acrylate, glycidyl methacrylate;
the co-stabilizer is selected from at least one of the following: aliphatic straight chain or branched chain alkane of C14-C22, aliphatic alcohol of C14-C22;
(3) mixing the dispersed dye particle water dispersion liquid obtained in the step (1) with the monomer micro-suspension liquid obtained in the step (2), and performing high-speed shearing treatment at 1000-18000 rpm for 0.5-200 min to obtain a monomer micro-suspension liquid containing the dispersed dye, wherein the mixing ratio of the dispersed dye particle water dispersion liquid to the monomer micro-suspension liquid is that the mass amount of the dispersed dye accounts for 10-900% of the total mass amount of the vinyl monomer; after nitrogen is introduced and oxygen is removed, the temperature is adjusted to 50-90 ℃, and the mixture reacts for 0.5-24 h under the protection of nitrogen, so as to prepare self-adhesive polymer/disperse dye composite particles;
and the initiator is introduced by the following means a or b:
in the step (2), adding an oil-soluble initiator into the oil phase solution, wherein the mass usage of the oil-soluble initiator is 0.05-5% of the total mass usage of the vinyl monomer;
mode b: in the step (3), a water-soluble initiator is added to the monomer micro-suspension containing the disperse dye, wherein the mass usage of the water-soluble initiator is 0.05-5% of the total mass usage of the vinyl monomer.
2. The method of claim 1, wherein: the disperse dye is one or a combination of more of anthraquinone disperse dyes, azo disperse dyes and heterocyclic disperse dyes.
3. The method of claim 1, wherein: in the step (2), the emulsifier is selected from at least one of the following: tween-20, OP-10, MOA-9, sodium dodecyl sulfate, hexadecyl trimethyl ammonium bromide and dodecyl dimethyl sulfopropyl betaine.
4. The method of claim 1, wherein: in the step (2), the hydrophobic vinyl monomer is at least one of the following: isooctyl acrylate, butyl acrylate, methyl methacrylate, vinyl acetate, styrene; the polar vinyl monomer is at least one of the following: 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, methacrylic acid, acrylic acid, glycidyl methacrylate, glycidyl acrylate, N-methylolacrylamide, N-hydroxyethylacrylamide.
5. The method of claim 1, wherein: in the step (2), the co-stabilizer is aliphatic straight-chain or branched-chain alkane of C16-C22.
6. The method of claim 1, wherein: in the step (2), the oil-soluble initiator is selected from at least one of the following: azobisisobutyronitrile, azobisisovaleronitrile, azobisisoheptonitrile;
or in the step (3), the water-soluble initiator is selected from at least one of the following: 2, 2' -azobisbutylamidine dihydrochloride, azobiscyanovaleric acid.
7. The method of claim 1, wherein: in the step (3), the polymerization reaction temperature is 55-75 ℃; the reaction time is 1-24 h.
8. Self-adhesive polymer/disperse dye composite particles prepared by the preparation process according to claim 1.
9. Use of the self-adhesive polymer/disperse dye composite particles according to claim 8 in polyester hot-melt dyeing.
10. The use according to claim 9, characterized in that the use is in particular: self-adhesive polymer/disperse dye composite particles are prepared into the composite particles with the concentration of 20 g.L-1～80g·L-1The polyester fabric is mixed with the dye bath, and is subjected to padding to obtain the polyester fabric with the mangle ratio of 30-85 percent, the polyester fabric is placed at the temperature of 70-120 ℃ for pre-drying for 5-10 min, then is subjected to high-temperature baking and color fixing for 1-5 min at the temperature of 170-230 ℃, and the finished product of the polyester yarn-dyed fabric is obtained after the temperature is reduced to below 50 ℃.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112301759A (en) * | 2020-11-04 | 2021-02-02 | 郎溪远华纺织有限公司 | Dyeing process of Teflon polyester fabric |
| CN115305021A (en) * | 2022-09-29 | 2022-11-08 | 潍坊德高新材料有限公司 | Colored cyanoacrylate adhesive and preparation method thereof |
| CN115701438A (en) * | 2021-08-02 | 2023-02-10 | 南亚塑胶工业股份有限公司 | Water-based acrylic resin and manufacturing method thereof |
| CN116102902A (en) * | 2023-03-03 | 2023-05-12 | 浙江理工大学绍兴柯桥研究院有限公司 | Preparation method of high-concentration liquid disperse dye |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1456613A (en) * | 2003-05-13 | 2003-11-19 | 唐二军 | One-step microsuspension powdered coating manufacturing method |
| CN101531830A (en) * | 2009-04-23 | 2009-09-16 | 浙江理工大学 | Preparation method of self-adhesive organic pigment microcapsules for pigment printing |
| CN101652723A (en) * | 2007-02-23 | 2010-02-17 | 三星精密化学株式会社 | Method of preparing toner having core-shell structure and toner prepared using the same |
| CN101955692A (en) * | 2010-08-10 | 2011-01-26 | 浙江理工大学 | Method for preparing pulpy disperse dye for low-temperature dyeing of terylene |
| CN104530288A (en) * | 2014-12-22 | 2015-04-22 | 常熟市环虹化工颜料厂 | Method for controlling particle size of microcapsule pigment |
-
2020
- 2020-06-30 CN CN202010619887.8A patent/CN111662405B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1456613A (en) * | 2003-05-13 | 2003-11-19 | 唐二军 | One-step microsuspension powdered coating manufacturing method |
| CN101652723A (en) * | 2007-02-23 | 2010-02-17 | 三星精密化学株式会社 | Method of preparing toner having core-shell structure and toner prepared using the same |
| CN101531830A (en) * | 2009-04-23 | 2009-09-16 | 浙江理工大学 | Preparation method of self-adhesive organic pigment microcapsules for pigment printing |
| CN101955692A (en) * | 2010-08-10 | 2011-01-26 | 浙江理工大学 | Method for preparing pulpy disperse dye for low-temperature dyeing of terylene |
| CN104530288A (en) * | 2014-12-22 | 2015-04-22 | 常熟市环虹化工颜料厂 | Method for controlling particle size of microcapsule pigment |
Non-Patent Citations (3)
| Title |
|---|
| 戚栋明等: "微悬浮法制备有机颜料微胶囊中的粒径调控", 《化工学报》 * |
| 戚栋明等: "有机颜料酞菁蓝微胶囊的原位微悬浮法制备及其表征", 《高分子学报》 * |
| 陈智杰等: "有机颜料微胶囊形态对棉织物涂料印花效果的影响", 《纺织学报》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112301759A (en) * | 2020-11-04 | 2021-02-02 | 郎溪远华纺织有限公司 | Dyeing process of Teflon polyester fabric |
| CN115701438A (en) * | 2021-08-02 | 2023-02-10 | 南亚塑胶工业股份有限公司 | Water-based acrylic resin and manufacturing method thereof |
| CN115305021A (en) * | 2022-09-29 | 2022-11-08 | 潍坊德高新材料有限公司 | Colored cyanoacrylate adhesive and preparation method thereof |
| CN116102902A (en) * | 2023-03-03 | 2023-05-12 | 浙江理工大学绍兴柯桥研究院有限公司 | Preparation method of high-concentration liquid disperse dye |
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