CN113083153A - Dispersing agent, preparation method and application thereof, and disperse dye color paste - Google Patents

Dispersing agent, preparation method and application thereof, and disperse dye color paste Download PDF

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CN113083153A
CN113083153A CN202110389624.7A CN202110389624A CN113083153A CN 113083153 A CN113083153 A CN 113083153A CN 202110389624 A CN202110389624 A CN 202110389624A CN 113083153 A CN113083153 A CN 113083153A
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dispersant
disperse dye
color paste
solvent
monomer
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王莹铮
张云杰
刘明辉
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TRENDVISION ELECTRONICS SCIENCE TECHNOLOGY (ZHUHAI) CO LTD
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TRENDVISION ELECTRONICS SCIENCE TECHNOLOGY (ZHUHAI) CO LTD
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/16—Amines or polyamines
    • 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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
    • C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008—Preparations of disperse dyes or solvent dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Dispersion Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

The invention relates to the technical field of digital printing, and provides a dispersing agent, a preparation method and application thereof, and disperse dye color paste. The invention takes amido, benzene ring or heterocycle as anchor group, the dispersant can be firmly adsorbed on the surface of dye particle to prevent the dispersant from desorption, meanwhile, the invention forms solvation chain with polyester, polyether, polyolefin or polyacrylate, the solvation chain has good compatibility with the dispersion medium, and can be stretched in the dispersion medium to form steric hindrance to prevent the particle from flocculating. The dispersing dye color paste prepared by the dispersing agent has high stability and is not easy to settle; furthermore, the invention has excellent dispersibility for disperse dyes of yellow, red, blue, orange and brown, and can obtain black color paste with high stability by mixing colors of brown, blue and yellow or orange, blue and yellow.

Description

Dispersing agent, preparation method and application thereof, and disperse dye color paste
Technical Field
The invention relates to the technical field of digital printing, in particular to a dispersing agent, a preparation method and application thereof and disperse dye color paste.
Background
Digital printing is a technique in which a pattern is printed on a material in a direct or indirect manner after color separation and conversion by a computer. In recent years, environmental awareness is deepened, regulations are also strict, and according to the statistics of Konica Minolta, the sewage discharge generated by digital printing is only 15% of that of the traditional printing, more than 50% of energy consumption and 80% of carbon dioxide discharge can be reduced, so that the digital printing market has gradually increased in recent years and replaces the traditional printing market, and the digital printing ink is widely applied to the textile, home decoration and advertisement industries.
In the textile industry, the market demand is mainly in small-batch customized production, and the advantages of changeable templates, high printing precision and rapid delivery exist. The traditional textile printing and dyeing process is labor-consuming and pollution-intensive, and needs mould opening and plate making for mass production to reduce cost, and has the defect of long delivery cycle.
According to Market analysis predictions of Allied Market Research, the global digital printing textile Market will steadily grow with an annual composite growth rate of 17.9%, and the development of digital printing inks will dominate thermal sublimation (disperse dye) inks. However, the precision of the nozzle configured for the digital printer is high, the aperture is generally 0.02-0.05 mm, and in order to avoid the damage of the nozzle caused by the ink blockage, the required ink needs higher quality and stability compared with the traditional printing. The main raw materials of the thermal sublimation ink are disperse dye, dispersant, water, auxiliary agent and the like, the disperse dye cannot be dissolved in water and needs to be ground and dispersed into nano-scale suspension, and the stability of the thermal sublimation ink mainly depends on the quality of the disperse dye and the matching degree of the dispersant and the disperse dye.
In the art, disperse dyes are of varying quality and few dispersants are developed in the market for digital printing grade inks, most of which are dominated by traditional paint applications. In the four-color ink of yellow, red, blue and black, the quality of black is most difficult to control, and no black exists in the disperse dyes, so that the black is mostly mixed with brown, blue and yellow or orange, blue and yellow, wherein the disperse dyes of brown and orange are difficult to disperse, and the dispersant which can be matched in the market is very rare, so that the produced black sublimation ink has poor quality, the quality guarantee period is shortened, and the problem of flocculation occurs in a short time.
Disclosure of Invention
In view of the above, the invention aims to provide a dispersing agent, a preparation method and an application thereof, and a disperse dye color paste. The dispersant provided by the invention has good dispersibility and high stability, and the dispersant can be used for obtaining disperse dye color paste with high stability, especially black disperse dye color paste with stable dispersion.
In order to achieve the above object, the present invention provides the following technical solutions:
a dispersing agent comprises the following preparation raw materials in parts by mass: 3-30% of anchoring group monomer, 10-50% of solvation chain monomer, 1-12% of initiator and 40-60% of solvent;
the anchoring group monomer comprises one or more of a monomer containing amido, a monomer containing benzene ring and a monomer containing heterocycle;
the solvating chain monomer comprises one or more of polyester, polyether, polyolefin and polyacrylate.
Preferably, the anchoring group monomer comprises one or more of N-methylol acrylamide, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, dimethylaminopropyl methacrylamide, N- (3-aminopropyl) methacrylamide hydrochloride, N- (2-aminoethyl) methacrylamide hydrochloride, N-dimethylacrylamide, N-acryloyl morpholine, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate and methyl benzyl acrylate.
Preferably, the solvent chain monomer comprises one or more of polyethylene glycol monomethyl ether acrylate, polyethylene glycol monoethyl ether acrylate, polyethylene glycol monomethyl ether methacrylate and polyethylene glycol monoethyl ether methacrylate.
Preferably, the initiator comprises one or more of azobisisoheptonitrile, azobisisobutyronitrile, azobisisovaleronitrile, dimethyl azobisisobutyrate, azobisisobutyramidine hydrochloride, azobisisobutyrimidazoline hydrochloride, azobisisobutyronitrile formamide, azobiscyclohexylcarbonitrile and azobiscyanovaleric acid;
the solvent comprises one or more of water, an alcohol solvent, a ketone solvent, an ester solvent, a benzene solvent, halogenated alkane and tetrahydrofuran.
The invention also provides a preparation method of the dispersant, which comprises the following steps:
and mixing the anchoring group monomer, the solvation chain monomer, the initiator and the solvent for polymerization reaction to obtain the dispersing agent.
Preferably, the mixing to effect polymerization comprises:
mixing an anchoring group monomer and a solvation chain monomer to obtain a premixed liquid A;
mixing an initiator and a part of solvent to obtain a premixed solution B;
and adding the premix A and the premix B into the rest of the solvent to carry out polymerization reaction.
Preferably, the temperature of the polymerization reaction is 70-80 ℃, and the time is 4-6 h.
The invention also provides application of the dispersant in the scheme or the dispersant prepared by the preparation method in the scheme in dispersing dye color paste.
The invention also provides a disperse dye color paste, which comprises the following preparation raw materials in parts by mass: 5-40% of a dispersant, 10-40% of a disperse dye and 20-85% of a dispersion medium; the dispersant is the dispersant described in the above scheme or the dispersant prepared by the preparation method described in the above scheme.
Preferably, the disperse dye comprises one or more of blue disperse dye, red disperse dye, yellow disperse dye, orange disperse dye and brown disperse dye.
The invention provides a dispersing agent, which is prepared from the following raw materials in parts by mass: 3-30% of anchoring group monomer, 10-50% of solvation chain monomer, 1-12% of initiator and 40-60% of solvent; the anchoring group monomer comprises one or more of a monomer containing amido, a monomer containing benzene ring and a monomer containing heterocycle; the solvating chain monomer comprises one or more of polyester, polyether, polyolefin and polyacrylate. The invention takes amido, benzene ring or heterocycle as anchor group, the obtained dispersant can be adsorbed on the surface of dye particle by using the functions of pi bond, hydrogen bond, van der waals force and the like to prevent the dispersant from desorbing, and simultaneously the invention forms a solvation chain by polyester, polyether, polyolefin or polyacrylate, the solvation chain has good compatibility with a dispersion medium, and can be stretched in the dispersion medium to form steric hindrance to prevent the particle from flocculating. The dispersing agent provided by the invention has good dispersibility and high stability, and can be used for preparing disperse dye color paste with high stability.
The invention also provides a preparation method of the dispersant, which has simple steps and is easy to operate.
The invention also provides disperse dye color paste, and the preparation raw materials comprise a dispersant, disperse dye and a dispersion medium. The dispersing dye color paste prepared by the dispersing agent has high stability and is not easy to settle; furthermore, the invention has excellent dispersibility for disperse dyes of yellow, red, blue, orange and brown, and can obtain black color paste with high stability by mixing colors of brown, blue and yellow or orange, blue and yellow.
Detailed Description
The invention provides a dispersing agent, which comprises the following preparation raw materials in parts by mass: 3-30% of anchoring group monomer, 10-50% of solvation chain monomer, 1-12% of initiator and 40-60% of solvent.
The raw materials for preparing the dispersant provided by the invention comprise 3-30% of anchoring group monomer, preferably 5-25% of anchoring group monomer by mass fraction. In the invention, the anchoring group monomer comprises one or more of a monomer containing amido, a monomer containing benzene ring and a monomer containing heterocycle; more preferably comprises one or more of N-methylolacrylamide, acrylamide, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, dimethylaminopropyl methacrylamide, N- (3-aminopropyl) methacrylamide hydrochloride, N- (2-aminoethyl) methacrylamide hydrochloride, N-dimethylacrylamide, N-acryloylmorpholine, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate and methyl benzyl acrylate.
The raw materials for preparing the dispersant provided by the invention comprise 10-50% of solvation chain monomer, preferably 20-40% by mass. In the invention, the solvating chain monomer comprises one or more of polyester, polyether, polyolefin and polyacrylate, the polyester is preferably polyacrylate, and the weight average molecular weight (M) of the solvating chain monomerw) Preferably 300 to 2000, more preferably 500 to 1500; specifically, the polyacrylate preferably comprises one or more of polyethylene glycol monomethyl ether acrylate, polyethylene glycol monoethyl ether acrylate, polyethylene glycol monomethyl ether methacrylate and polyethylene glycol monoethyl ether methacrylate; in the specific embodiment of the invention, the polyethylene glycol monomethyl ether methacrylate is preferably in the type of MPEGMA400, MPEGMA600 or MPEGMA 1000; the type of the polyethylene glycol monomethyl ether acrylate is preferably MPEGA400 or MPEGA 600.
The preparation raw material of the dispersant provided by the invention comprises 1-12% of an initiator by mass fraction, and preferably 5-10% of the initiator by mass fraction. In the present invention, the initiator preferably includes one or more of azobisisoheptonitrile, azobisisobutyronitrile, azobisisovaleronitrile, dimethyl azobisisobutyrate, azobisisobutyramidine hydrochloride, azobisisobutyrimidazoline hydrochloride, azobisisobutyronitrile formamide, azobiscyclohexylcarbonitrile, and azobiscyanovaleric acid.
The raw materials for preparing the dispersant provided by the invention comprise 40-60% of solvent by mass fraction, and preferably 45-55% of solvent by mass fraction. In the invention, the solvent preferably comprises one or more of water, an alcohol solvent, a ketone solvent, an ester solvent, a benzene solvent, halogenated alkane and tetrahydrofuran; the alcohol solvent preferably comprises one or more of methanol, ethanol, propanol, isopropanol and dipropylene glycol; one or more of acetone, butanone, methyl isobutyl ketone and cyclohexanone serving as ketone solvents; the ester solvent preferably comprises one or more of ethyl acetate, butyl acetate and isopropyl acetate; the halogenated alkane preferably comprises dichloromethane and/or dichloroethane; the benzene-based solvent preferably includes toluene and/or xylene.
The invention also provides a preparation method of the dispersant, which comprises the following steps:
and mixing the anchoring group monomer, the solvation chain monomer, the initiator and the solvent for polymerization reaction to obtain the dispersing agent.
In the present invention, the mixing for polymerization preferably comprises:
mixing an anchoring group monomer and a solvation chain monomer to obtain a premixed liquid A;
mixing an initiator and a part of solvent to obtain a premixed solution B;
and adding the premix A and the premix B into the rest of the solvent to carry out polymerization reaction.
The invention has no special requirements on the mixing method, and the raw materials can be uniformly mixed; the invention has no special requirement on the concentration of the initiator in the premix B, and the initiator can be completely dissolved.
In the invention, the temperature of the polymerization reaction is preferably 70-80 ℃, more preferably 73-75 ℃, and the time of the polymerization reaction is preferably 4-6 h, more preferably 4.5-5.5 h; the polymerization reaction is preferably carried out under the protection of nitrogen; in the specific embodiment of the invention, the polymerization reaction is preferably carried out in a reaction bottle provided with a condensing reflux device, the residual solvent is preferably added into the reaction bottle firstly, and then the premixed liquid A and the premixed liquid B are slowly added into the reaction bottle at the same time, in the specific embodiment of the invention, the adding rates of the premixed liquid A and the premixed liquid B are preferably controlled according to the total amount of reaction raw materials, the adding rate is faster when the consumption of the raw materials is larger, specifically, the adding time of the premixed liquid A is preferably controlled to be 3-4 h, the adding rate of the premixed liquid B is preferably controlled to be 3.5-4.5 h, the premixed liquid A is preferably added 0.5h earlier than the premixed liquid B, so as to ensure the polymerization degree of the monomer; in the invention, after the addition of the premixed liquid A and the premixed liquid B is finished, the heat is preserved for 0.5-2 h, and the time of the polymerization reaction is counted from the time when the premixed liquid A and the premixed liquid B are added;
in the embodiment of the present invention, when solid monomers (for example, MPEGMA1000) are present in the anchor group monomers and the solvating chain monomers used, the present invention preferably mixes the liquid monomers to obtain a pre-mixed solution a1, dissolves the solid monomers in a part of the solvent to obtain a pre-mixed solution a2, and then adds the pre-mixed solutions a1 and a2 and the pre-mixed solution B described in the above scheme into a reaction bottle at the same time for reaction, wherein the adding rates of the pre-mixed solutions a1 and a2 are preferably the same.
In the embodiment of the present invention, it is preferable to determine the reaction completion time by detecting the total residual amount of the reaction monomers in the system during the reaction, and specifically, when the total residual amount of the reaction monomers in the system is less than 3 wt.%, the heating is stopped and the polymerization reaction is completed.
In the invention, after the polymerization reaction is finished, the obtained product liquid is a dispersant solution, and the mass fraction of the dispersant in the dispersant solution is 50-60%, preferably 53-55%; in a specific embodiment of the present invention, the mass fraction of the dispersant solution can be specifically tested by the following method: and baking the obtained dispersant solution at 150 ℃ for 2h to obtain a remainder, namely a non-volatile part (namely the dispersant of the invention), wherein the ratio of the mass of the non-volatile part to the total mass of the dispersant solution is the mass fraction of the dispersant solution.
The invention also provides application of the dispersant in the scheme in dispersing dye color paste. The dispersing agent is utilized to prepare the disperse dye color paste, and the obtained color paste has good dispersion stability and is not easy to settle.
The invention also provides a disperse dye color paste, which comprises the following preparation raw materials in parts by mass: 5-40% of a dispersing agent, 10-40% of a disperse dye and 20-85% of a dispersing medium.
The raw materials for preparing the disperse dye color paste comprise 5-40% by mass of a dispersing agent, and preferably 10-30%. In the invention, the dispersant is the dispersant described in the above scheme or the dispersant prepared by the preparation method described in the above scheme; in the invention, when the disperse dye color paste is prepared, the dispersant solution prepared by the scheme is directly used for preparation, the mass of the dispersant is calculated by the effective mass of the dispersant in the dispersant solution (namely the mass of a non-volatile part), and the mass of a part of solvent introduced into the dispersant solution is calculated in the mass of a dispersion medium.
The raw materials for preparing the disperse dye color paste comprise, by mass, 10-40% of disperse dye, and preferably 20-30%. In the present invention, the disperse dye preferably includes one or more of a blue disperse dye, a red disperse dye, a yellow disperse dye, an orange disperse dye and a brown disperse dye; preferred include one or more of the following disperse dyes: blue disperse dye 14, 28, 56, 72, 87, 165, 359, 360, 366; red disperse dye 4, 11, 22, 54, 60, 74, 82, 92, 146, 278; yellow disperse dyes 3, 23, 42, 51, 54, 60, 65, 82, 98, 160, 211; orange disperse dyes 1, 3, 25, 29, 30, 37, 61, 76, 149, 288; brown disperse dye 27.
In the art, the commonly used colorants of black disperse dye ink are mainly disperse brown 27, disperse blue 360, disperse orange 25, and disperse yellow 54, wherein disperse brown 27 is the most difficult to grind and disperse and the suspension stability is the worst, and disperse blue 360 and disperse orange 25 are the second most easy to grind and disperse than disperse brown 27, but the stability is inferior to other commonly used color colorants (e.g. disperse yellow 54 and disperse red 60). The difference is mainly caused by the chemical structure (the structural formulas of disperse brown 27, disperse blue 360, disperse orange 25, disperse yellow 54 and disperse red 60 are as follows), and the aromatic ring in the chemical structure of the pigment is provided with a nitro group, so that the applicability of the commonly used dispersant in the market is reduced. The dispersing agent commonly used in the disperse dye ink includes sodium lignosulfonate, acrylate derivatives and the like, and mostly utilizes pi bonds of aromatic rings on the dispersing agent and pi bonds on the pigment to generate adsorption force, and generates repulsion force or steric hindrance to stabilize suspension liquid by negative charges carried by the dispersing agent. However, in the case of disperse brown 27, one benzene ring is substituted by nitro and two chlorine, the nitro group is rich in electrons and is a strong electron-pulling group, which affects pi bond attraction, and the chlorine substituent makes pi-pi orbital overlap difficult, which affects adsorption of the dispersant on the pigment, and thus suspension stability of disperse brown 27 is reduced.
When the dispersing agent is designed, a long-chain high-molecular structure (namely a solvent chain monomer) capable of playing a role of winding is introduced, and meanwhile, the water solubility of the dispersing agent is increased by selecting the anchoring group monomer and the solvent chain monomer with better water solubility, so that the adsorbability of the dispersing agent on the dispersed dye is increased, and the dispersing effect is improved.
Figure BDA0003016059050000071
In the invention, the black disperse dye color paste can be obtained by mixing brown, blue and yellow or orange, blue and yellow. The black disperse dye color paste provided by the invention is stable in dispersion and not easy to settle.
The raw materials for preparing the disperse dye color paste comprise, by mass, 20-85% of a dispersion medium, and preferably 30-80%. In the invention, the dispersion medium preferably comprises one or more of water, an ether solvent, an ester solvent, a ketone solvent and an alcohol solvent, wherein the ether solvent is preferably triethylene glycol monobutyl ether, and the alcohol solvent is preferably one or more of glycerol, ethylene glycol, diethylene glycol and isopropanol; the ester solvent is preferably ethyl acetate and/or butyl acetate, and the ketone solvent is preferably 2-pyrrolidone.
In the invention, the preparation method of the disperse dye color paste preferably comprises the following steps:
mixing a dispersing agent and a dispersing medium to obtain a pre-solution; mixing the disperse dye and the pre-solution to obtain a pre-dispersion solution;
and grinding the pre-dispersion liquid and filtering to obtain a filtrate, namely the disperse dye color paste.
In the invention, the grinding is preferably carried out in a sand mill, and the grinding is preferably carried out until the average particle size of the color paste is 50-150 nm, more preferably 80-120 nm; the invention has no special requirements on the grinding conditions, and can obtain the color paste with the grain diameter meeting the requirements.
In the present invention, the filtration membrane is preferably a PVDF membrane having a pore size of 1 μm; the invention removes colloid and large-particle-size particles by filtering to obtain the disperse dye color paste with stable dispersion.
The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention.
Example 1
Introducing nitrogen into a reaction bottle provided with a condensation reflux device, adding 150g of water and 210g of isopropanol, and heating to 70-80 ℃; then mixing 80g of dimethylaminoethyl methacrylate, 120g of methylbenzyl acrylate and 320g of polyethylene glycol monomethyl ether methacrylate (molecular weight is 400, MPEGMA400) to obtain a premixed solution A; then, 102g of butanone and 18g of azobisisobutyronitrile are mixed and stirred until the mixture is dissolved, so as to obtain a premixed solution B; then slowly adding the premixed liquid A and the premixed liquid B into a reaction bottle for reaction, wherein the premixed liquid A is added 0.5h earlier than the premixed liquid B; after about 4 hours of reaction, the reaction was terminated by detecting that the amount of the residual monomer was less than 5%, to obtain dispersant A (54.9% in effective amount).
Example 2
Introducing nitrogen into a reaction bottle provided with a condensation reflux device, adding 150g of water and 210g of isopropanol, and heating to 70-80 ℃; then, 80g of dimethylaminoethyl methacrylate, 110g of methylbenzyl acrylate and 330g of polyethylene glycol monomethyl ether methacrylate (molecular weight is 600, MPEGMA600) are mixed to obtain a premixed solution A; then, 102g of butanone and 18g of azobisisobutyronitrile are mixed and stirred until the mixture is dissolved, so as to obtain a premixed solution B; then slowly adding the premixed liquid A and the premixed liquid B into a reaction bottle for reaction, wherein the premixed liquid A is added 0.5h earlier than the premixed liquid B; after about 4 hours of reaction, the reaction was terminated by detecting that the amount of the residual monomer was less than 5%, to obtain dispersant B (effective amount: 55.0%).
Example 3
Introducing nitrogen into a reaction bottle provided with a condensation reflux device, adding 150g of water and 210g of isopropanol, and heating to 70-80 ℃; then, 80g of dimethylaminoethyl methacrylate, 160g of methylbenzyl acrylate and 280g of polyethylene glycol monomethyl ether acrylate (molecular weight is 600, MPEGA600) are mixed to obtain a premixed solution A; then 102g of water and 18g of azodicyano valeric acid are mixed and stirred until dissolved to obtain a premixed solution B; then slowly adding the premixed liquid A and the premixed liquid B into a reaction bottle for reaction, wherein the premixed liquid A is added 0.5h earlier than the premixed liquid B; after about 4 hours of reaction, the reaction was terminated by detecting that the amount of the residual monomer was less than 5%, to obtain dispersant C (53.0% in terms of effective amount).
Example 4
Introducing nitrogen into a reaction bottle provided with a condensation reflux device, adding 50g of water and 160g of isopropanol, and heating to 70-80 ℃; then 80g of dimethylaminoethyl methacrylate and 200g of 2-phenoxyethyl acrylate are mixed to obtain a premixed solution A1; 240g of polyethylene glycol monomethyl ether acrylate (molecular weight 1000, MPEGMA1000) and 150g of water are mixed to obtain a premixed solution A2; then 102g of water and 18g of azodicyano valeric acid are mixed and stirred until dissolved to obtain a premixed solution B; then slowly adding the premixed liquid A1, the premixed liquid A2 and the premixed liquid B into a reaction bottle for reaction, wherein the premixed liquid A1 and the premixed liquid A2 are added 0.5h earlier than the premixed liquid B; after about 4 hours of reaction, the reaction was terminated by detecting that the amount of the residual monomer was less than 5%, to obtain dispersant D (53.1% in terms of effective amount).
Example 5
Introducing nitrogen into a reaction bottle provided with a condensing reflux device, adding 200g of water and 160g of isopropanol, and heating to 70-80 ℃; then 90g of N- (3-aminopropyl) methacrylamide hydrochloride, 190g of 2-phenoxyethyl acrylate and 240g of polyethylene glycol monomethyl ether acrylate with the molecular weight of 400(MPEGA400) are mixed to obtain a premixed solution A; then 102g of water and 18g of azodicyano valeric acid are mixed and stirred until dissolved to obtain a premixed solution B; then slowly adding the premixed liquid A and the premixed liquid B into a reaction bottle for reaction, wherein the premixed liquid A is added 0.5h earlier than the premixed liquid B; after about 4 hours of reaction, the reaction was terminated by detecting that the amount of the residual monomer was less than 5%, to obtain dispersant E (effective component: 52.7%).
Example 6
Introducing nitrogen into a reaction bottle provided with a condensing reflux device, adding 200g of water and 160g of isopropanol, and heating to 70-80 ℃; then 90g of N- (3-aminopropyl) methacrylamide hydrochloride, 180g of 2-phenoxyethyl acrylate and 250g of polyethylene glycol monomethyl ether acrylate (molecular weight is 600, MPEGA600) are mixed to obtain a premixed solution A; then 102g of water and 18g of azodicyano valeric acid are mixed and stirred until dissolved to obtain a premixed solution B; then slowly adding the premixed liquid A and the premixed liquid B into a reaction bottle for reaction, wherein the premixed liquid A is added 0.5h earlier than the premixed liquid B; after 4 hours of reaction, the reaction was terminated by detecting that the amount of the residual monomer was less than 5%, to obtain dispersant F (52.7% in terms of effective amount).
Example 7
Introducing nitrogen into a reaction bottle provided with a condensing reflux device, adding 200g of water and 160g of isopropanol, and heating to 70-80 ℃; then 90g of N- (3-aminopropyl) methacrylamide hydrochloride, 180g of 2-phenoxyethyl acrylate and 250g of polyethylene glycol monomethyl ether methacrylate (molecular weight 600, MPEGMA600) are mixed to obtain a premixed solution A; then 102g of water and 18g of azodicyano valeric acid are mixed and stirred until dissolved to obtain a premixed solution B; then slowly adding the premixed liquid A and the premixed liquid B into a reaction bottle for reaction, wherein the premixed liquid A is added 0.5h earlier than the premixed liquid B; after 4 hours of reaction, the reaction was terminated by detecting that the amount of the remaining monomer was less than 5%, to obtain dispersant G (53.0% in terms of effective amount).
Example 8
Introducing nitrogen into a reaction bottle provided with a condensing reflux device, adding 200g of water and 160g of isopropanol, and heating to 70-80 ℃; then 90g of N- (3-aminopropyl) methacrylamide hydrochloride, 180g of methyl benzyl acrylate and 250g of polyethylene glycol monomethyl ether methacrylate (molecular weight is 600, MPEGMA600) are mixed to obtain a premixed solution A; then 102g of water and 18g of azodicyano valeric acid are mixed and stirred until dissolved to obtain a premixed solution B; then slowly adding the premixed liquid A and the premixed liquid B into a reaction bottle for reaction, wherein the premixed liquid A is added 0.5h earlier than the premixed liquid B; after 4 hours of reaction, the reaction was terminated by detecting that the amount of the remaining monomer was less than 5%, to obtain dispersant H (53.2% in terms of effective amount).
Example 9
Dissolving 200g of dispersant A in 200g of deionized water, mixing and stirring to completely dissolve to obtain a pre-solution; then, 100g of brown disperse dye 27 is added into the pre-solution, and the pre-dispersion solution is obtained by stirring the mixture to completely wet the pigment; then, the product is processedIntroducing the pre-dispersion liquid into a sand mill for grinding until D50The particle size is 120-150 nm; filtering to remove the colloid and the large particle size, and obtaining the brown disperse dye color paste with stable dispersion.
Example 10
Dissolving 180g of dispersant B in 220g of deionized water, mixing and stirring to completely dissolve to obtain a pre-solution; then, 100g of brown disperse dye 27 is added into the pre-solution, and the pre-dispersion solution is obtained by stirring the mixture to completely wet the pigment; then the pre-dispersion liquid is led into a sand mill for grinding until D50The particle size is 120-150 nm; filtering to remove the colloid and the large particle size, and obtaining the brown disperse dye color paste with stable dispersion.
Example 11
Dissolving 200g of dispersant C in 200g of deionized water, mixing and stirring to completely dissolve to obtain a pre-solution; then 100g of blue disperse dye 360 is added into the pre-solution, and the pre-dispersion solution is obtained by stirring the mixture to completely wet the pigment; then the pre-dispersion liquid is led into a sand mill for grinding until D50The particle size is 100-130 nm; filtering to remove the colloid and the large particle size, and obtaining the blue disperse dye color paste with stable dispersion.
Example 12
Dissolving 200g of dispersant D in 200g of deionized water, mixing and stirring to completely dissolve to obtain a pre-solution; then 100g of blue disperse dye 360 is added into the pre-solution, and the pre-dispersion solution is obtained by stirring the mixture to completely wet the pigment; then the pre-dispersion liquid is led into a sand mill for grinding until D50The particle size is 100-130 nm; filtering to remove the colloid and the large particle size, and obtaining the blue disperse dye color paste with stable dispersion.
Example 13
Dissolving 200g of dispersant E in 200g of deionized water, mixing and stirring to completely dissolve to obtain a pre-solution; then 100g of blue disperse dye 360 is added into the pre-solution, and the pre-dispersion solution is obtained by stirring the mixture to completely wet the pigment; then the pre-dispersion liquid is led into a sand mill for grinding until D50The particle size is 120-150 nm; filtering to remove the colloid and the large particle size, and obtaining the brown disperse dye color paste with stable dispersion.
Example 14
180g of dispersant F are dissolved in 220g of deionized water and mixedStirring and dissolving completely to obtain a pre-solution; then, 100g of brown disperse dye 27 is added into the pre-solution, and the pre-dispersion solution is obtained by stirring the mixture to completely wet the pigment; then the pre-dispersion liquid is led into a sand mill for grinding until D50The particle size is 120-150 nm; filtering to remove colloid and large-particle-size particles to obtain the brown disperse dye color paste with stable dispersion.
Example 15
Dissolving 180G of dispersant G in 220G of deionized water, mixing and stirring to completely dissolve to obtain a pre-solution; then, 100g of brown disperse dye 27 is added into the pre-solution, and the pre-dispersion solution is obtained by stirring the mixture to completely wet the pigment; then the pre-dispersion liquid is led into a sand mill for grinding until D50The particle size is 120-150 nm; filtering to remove colloid and large-particle-size particles to obtain the brown disperse dye color paste with stable dispersion.
Example 16
Dissolving 180g of dispersant H in 220g of deionized water, mixing and stirring to completely dissolve to obtain a pre-solution; then, 100g of brown disperse dye 27 is added into the pre-solution, and the pre-dispersion solution is obtained by stirring the mixture to completely wet the pigment; then the pre-dispersion liquid is led into a sand mill for grinding until D50The particle size is 120-150 nm; filtering to remove colloid and large-particle-size particles to obtain the brown disperse dye color paste with stable dispersion.
Example 17
160g of dispersant B is dissolved in 240g of deionized water, and the dispersant B and the deionized water are mixed, stirred and completely dissolved to obtain a pre-solution; then adding 100g of yellow disperse dye 54 into the pre-solution, and stirring to completely wet the pigment to obtain a pre-dispersion solution; then the pre-dispersion liquid is led into a sand mill for grinding until D50The particle size is 120-150 nm; filtering to remove the colloid and the large-particle-size particles, and obtaining the yellow color paste with stable dispersion.
Comparative example 1
160g of DISPERBYK-190 dispersant is dissolved in 240g of deionized water, and the mixture is mixed, stirred and completely dissolved to obtain a pre-solution; then 100g of brown disperse dye 27 is added into the pre-solution, the pre-dispersion liquid is obtained by stirring the pigment to be completely wetted, and the pre-dispersion liquid is led into a sand mill to be ground until D50The particle size is 120-150 nm.
Comparative example 2
Dissolving 160g of DISPERBYK-2010 dispersant in 240g of deionized water, mixing and stirring the mixture and dissolving the mixture completely to obtain a pre-solution; then 100g of brown disperse dye 27 is added into the pre-solution, the pre-dispersion liquid is obtained by stirring the pigment to be completely wetted, and the pre-dispersion liquid is led into a sand mill to be ground until D50The particle size is 120-150 nm.
Comparative example 3
Dissolving 160g of DISPERBYK-2012 dispersant in 240g of deionized water, mixing and stirring the mixture and dissolving the mixture completely to obtain a pre-solution; then 100g of brown disperse dye 27 is added into the pre-solution, the pre-dispersion liquid is obtained by stirring the pigment to be completely wetted, and the pre-dispersion liquid is led into a sand mill to be ground until D50The particle size is 120-150 nm.
Comparative example 4
Dissolving 160g of DISPERBYK-2012 dispersant in 240g of deionized water, mixing and stirring the mixture and dissolving the mixture completely to obtain a pre-solution; then 100g of blue disperse dye 360 is added into the pre-dispersion solution, the pre-dispersion solution is obtained by stirring to completely wet the pigment, and then the pre-dispersion solution is led into a sand mill to be ground until D50The particle size is 100 to 130 nm.
Product effectiveness testing
The color pastes prepared in the examples 9-17 and the comparative examples 1-4 are taken for stability test, and the stability test is as follows: and testing the particle size of the color paste at normal temperature, aging the color paste at 60 ℃ for 7 days, testing the particle size after aging for 7 days, and comparing and evaluating the particle size at normal temperature and after aging, wherein the particle size has small change and good stability.
The particle size measurement method comprises the following steps:
the measurement indexes include average particle diameter, D50、D100Wherein: d50: the physical meaning of the particle size corresponding to a cumulative particle size distribution of 50% for a sample is that the particle size is greater than 50% of the particle size and less than 50% of the particle size, D50Also called median or median particle diameter; d100: the physical meaning of the particle size corresponding to the cumulative particle size distribution of 100% for a sample is that the percentage of particles with a particle size smaller than 100%, D100It is commonly used to indicate the coarsest particle size index of the powder.
The results are shown in Table 1.
TABLE 1 color paste particle size at Normal temperature and high temperature (60 deg.C)
Figure BDA0003016059050000131
Figure BDA0003016059050000141
Because the properties of brown and blue disperse dyes are special, especially the disperse blue 360 is easy to have the condition of high change rate of particle size after color mixing, in the field, the D of the color paste100Less than 1000nm, and can pass through PVDF filter paper with the diameter of 1.0 mu m, and the color paste which meets the requirement can not block the spray head. As can be seen from the data in Table 1, the color pastes prepared in examples 9-17 have good stability, small particle size change after being placed at high temperature for 7 days, and D100The average energy can be kept below 650nm, and the color paste after being placed for 7 days at high temperature is subjected to filtration test, and the result shows that the color paste can pass 1.0 mu m PVDF filter paper. The comparative examples 1-4 have large particle size change after high temperature aging, wherein the color pastes of the comparative examples 1-3 even flocculate and become slurry, and the particle size can not be measured, although the color paste in the example 4 is placed at high temperature for 7 days, the color paste D has large particle size change100The particle size can be kept below 1000nm, but the particle size change is still larger compared with the blue color paste prepared by the dispersant (examples 11-12). The results show that the dispersing agent provided by the invention has good dispersion stability, and the dispersed dye color paste prepared by using the dispersing agent has high stability.
Example 18
The brown color paste prepared in example 10, the blue color paste prepared in example 11 and the yellow color paste prepared in example 17 were mixed to prepare a black color paste, and the stability of the obtained black color paste was tested, the test method being in accordance with the above-mentioned protocol.
The mixing ratio of the brown color paste, the blue color paste and the yellow color paste is shown in Table 2, and the test result of the stability of the black color paste is shown in Table 2.
TABLE 2 stability test results for black color pastes
Figure BDA0003016059050000142
In the art, black pastes after high temperature aging D50The particle size is hardly below 250nm, and it can be seen from the data in Table 2 that the average particle size of the black color paste obtained by the invention is only 80.4nm and D is obtained after mixing the brown, blue and yellow color pastes50The particle diameter is only 108nm, the average particle diameter after high-temperature treatment for 7 days is only 127.5nm, D50The particle size is only 139nm, which shows that the black color paste prepared by the dispersant has stable property. In the field, the stability of the monochromatic color paste is qualified when the black color paste is prepared, but the flocculation phenomenon occurs after color mixing.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.

Claims (10)

1. The dispersing agent is characterized by comprising the following preparation raw materials in parts by mass: 3-30% of anchoring group monomer, 10-50% of solvation chain monomer, 1-12% of initiator and 40-60% of solvent;
the anchoring group monomer comprises one or more of a monomer containing amido, a monomer containing benzene ring and a monomer containing heterocycle;
the solvating chain monomer comprises one or more of polyester, polyether, polyolefin and polyacrylate.
2. The dispersant of claim 1, wherein said anchor group monomer comprises one or more of N-methylol acrylamide, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, dimethylaminopropyl methacrylamide, N- (3-aminopropyl) methacrylamide hydrochloride, N- (2-aminoethyl) methacrylamide hydrochloride, N-dimethylacrylamide, N-acryloyl morpholine, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, and methyl benzyl acrylate.
3. The dispersant of claim 1, wherein the solvating chain monomer comprises one or more of polyethylene glycol monomethyl ether acrylate, polyethylene glycol monoethyl ether acrylate, polyethylene glycol monomethyl ether methacrylate and polyethylene glycol monoethyl ether methacrylate.
4. The dispersant of claim 1, wherein said initiator comprises one or more of azobisisoheptonitrile, azobisisobutyronitrile, azobisisovaleronitrile, dimethyl azobisisobutyrate, azobisisobutyramidine hydrochloride, azobisisobutyrimidazoline hydrochloride, azobisisobutyronitrile formamide, azobiscyclohexylcarbonitrile, and azobiscyanovaleric acid;
the solvent comprises one or more of water, an alcohol solvent, a ketone solvent, an ester solvent, a benzene solvent, halogenated alkane and tetrahydrofuran.
5. A method for preparing the dispersant of any one of claims 1 to 4, characterized by comprising the steps of:
and mixing the anchoring group monomer, the solvation chain monomer, the initiator and the solvent for polymerization reaction to obtain the dispersing agent.
6. The method of claim 5, wherein the mixing to effect polymerization comprises:
mixing an anchoring group monomer and a solvation chain monomer to obtain a premixed liquid A;
mixing an initiator and a part of solvent to obtain a premixed solution B;
and adding the premix A and the premix B into the rest of the solvent to carry out polymerization reaction.
7. The method according to claim 5 or 6, wherein the polymerization reaction is carried out at a temperature of 70 to 80 ℃ for 4 to 6 hours.
8. The dispersant of any one of claims 1 to 4 or the dispersant prepared by the preparation method of any one of claims 5 to 7 is applied to disperse dye color paste.
9. The disperse dye color paste is characterized by comprising the following preparation raw materials in parts by mass: 5-40% of a dispersant, 10-40% of a disperse dye and 20-85% of a dispersion medium; the dispersant is the dispersant as described in any one of claims 1 to 4 or the dispersant prepared by the preparation method as described in any one of claims 5 to 7.
10. The disperse dye color paste according to claim 9, wherein the disperse dye comprises one or more of blue disperse dye, red disperse dye, yellow disperse dye, orange disperse dye and brown disperse dye.
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CN116023798A (en) * 2022-12-29 2023-04-28 晋江市新胜星化工科技有限公司 Superfine liquid disperse dye and preparation process thereof
CN116285414A (en) * 2022-12-29 2023-06-23 晋江市新胜星化工科技有限公司 Preparation process of high-stability liquid disperse dye

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CN111574659A (en) * 2020-04-17 2020-08-25 传美讯电子科技（珠海）有限公司 Dispersant containing multi-element structure, color paste containing dispersant and UV ink jet

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CN111117375A (en) * 2020-01-02 2020-05-08 传美讯电子科技（珠海）有限公司 Color paste for water-based ink and preparation method thereof
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