CN111116843B - Grafting type dispersing agent and preparation method and application thereof - Google Patents
Grafting type dispersing agent and preparation method and application thereof Download PDFInfo
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- CN111116843B CN111116843B CN202010001798.7A CN202010001798A CN111116843B CN 111116843 B CN111116843 B CN 111116843B CN 202010001798 A CN202010001798 A CN 202010001798A CN 111116843 B CN111116843 B CN 111116843B
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- methacrylate
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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
- 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
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/322—Pigment inks
Abstract
The invention belongs to the field of coatings, and discloses a grafting type dispersing agent which is mainly prepared from a main chain monomer, a branched chain monomer, an initiator and a solvent, wherein the mass ratio of the main chain monomer to the branched chain monomer is (1-2) to (1-15); the main chain monomer comprises a monomer containing an aromatic group and a monomer containing an acid base, and the branched chain monomer is selected from at least one of polyethylene glycol monomethyl ether methacrylate, polyethylene glycol methacrylate, polypropylene glycol monomethyl ether methacrylate or polypropylene glycol methacrylate. The grafted dispersing agent is low in production cost and excellent in dispersing performance, and can be used for preparing UV ink color paste with good stability.
Description
Technical Field
The invention belongs to the field of coatings, and particularly relates to a graft type dispersing agent, and a preparation method and application thereof.
Background
The UV ink is characterized by solvent free, 100% ink transfer. The UV ink is sprayed and printed on a medium material and can be formed through UV light curing, so the UV ink is also called as environment-friendly ink. The ink has the capability of adhering to a non-porous substrate, has good water resistance, chemical resistance, light resistance and weather resistance, and is regarded as all-round ink.
UV light curable inks have already taken up a large market share in conventional ink technology, but currently only a small part of the ink jet printing market. In addition to the fact that the ink-jet ink is limited by the choice of the print head and the need to use a low viscosity and high stability ink, the conventional low-cost and high viscosity UV ink cannot be used, another important reason is that the raw material and technical cost of the UV ink-jet ink are too high, which leads to a high price of the ink and thus cannot compete with the conventional solvent-based ink-jet ink. The UV ink-jet ink often has defects of nozzle blockage, ink drop oblique jetting or ink breaking and the like due to the problems of stability and viscosity. In order to overcome the defects, special specification monomers, resins, dispersing agents and the like with low viscosity and high dispersion stability are often adopted; or complicated production process and equipment are adopted, which is a significant reason for the high cost of raw materials and technology.
Therefore, the invention hopes to provide the dispersing agent which has lower cost and excellent dispersing performance and can be used for preparing the UV ink color paste with good stability.
Disclosure of Invention
The present invention is directed to solving at least one of the problems of the prior art described above. Therefore, the invention provides a grafting type dispersing agent which is low in production cost and excellent in dispersing performance and can be used for preparing UV ink color paste with good stability.
A graft type dispersant is mainly prepared from a main chain monomer, a branched chain monomer, an initiator and a solvent, wherein the mass ratio of the main chain monomer to the branched chain monomer is (1-2) to (1-15);
the main chain monomer comprises a monomer containing an aromatic group and a monomer containing an acid base, and the branched chain monomer is selected from at least one of polyethylene glycol monomethyl ether methacrylate, polyethylene glycol methacrylate, polypropylene glycol monomethyl ether methacrylate or polypropylene glycol methacrylate.
Wherein the acid-containing base represents at least one of an acid-containing group or a basic group.
Preferably, the aromatic group-containing monomer is at least one selected from the group consisting of 2-phenoxyethyl methacrylate, 2-phenoxyethyl acrylate, polyethylene glycol nonylphenyl ether acrylate, polypropylene glycol 4-nonylphenyl ether acrylate, polyethylene glycol nonylphenyl ether acrylate, polypropylene glycol nonylphenyl ether acrylate and o-phenylphenoxyethyl acrylate
Preferably, the monomer containing an acid base is selected from at least one of methacrylic acid, maleic acid, fumaric acid, vinylsulfonate, styrenesulfonate, vinylphosphate, methacrylamide, methylolacrylamide, hydroxyethylacrylamide, hydroxypropylacrylamide, vinylimidazole, vinylcaprolactam, N-dimethylacrylamide, N-acryloylmorpholine or N-vinylpyrrolidone.
Preferably, the degree of polymerization of the branched monomer is 10 to 200.
More preferably, the degree of polymerization of the branched monomer is 20 to 100.
A preparation method of a graft type dispersant comprises the following steps:
(1) mixing a main chain monomer and a branched chain monomer to obtain a premixed solution A; dissolving an initiator by using a solvent to obtain a premixed solution B;
(2) and mixing the premixed solution A and the premixed solution B for reaction under the protective gas environment to obtain the graft type dispersing agent.
And detecting that the reaction can be stopped when the residual monomer content is less than 5 percent to prepare the graft type dispersing agent.
Preferably, the initiator in step (1) is selected from at least one of azobisisoheptonitrile, azobisisobutyronitrile, azobisisovaleronitrile, dimethyl azobisisobutyrate, azobisisobutyramidine hydrochloride, azobisisobutyrimidazoline hydrochloride, azobisisobutyronitrile formamide or azobisdicyclohexyl carbonitrile.
Preferably, the solvent in step (1) is at least one selected from ethanol, propanol, isopropanol, butanone, methyl isobutyl ketone, ethyl acetate, isopropyl acetate, dichloromethane, acetone, dichloroethane, toluene, xylene, tetrahydrofuran, and cyclohexanone. The amount of the solvent used in the present invention is not particularly limited, and the initiator can be sufficiently dissolved.
Preferably, the reaction temperature in the step (2) is 70-80 ℃, and the reaction time is 4-7 h.
The UV ink-jet color paste comprises the following components in parts by weight:
preferably, the monomer is selected from at least one of tetrahydrofurfuryl acrylate, cyclo-trimethylolpropane formal acrylate, trimethylol cyclohexyl acrylate, 2-phenoxyethyl acrylate, benzyl acrylate, isobornyl acrylate, ethoxyethoxyethyl acrylate, 1, 6-hexanediol diacrylate, poly (ethylene glycol) phenyl ether acrylate, 1, 6-hexanediol ethoxylate diacrylate, neopentyl glycol polyethylene oxide diacrylate, tripropylene glycol diacrylate, dipropylene glycol diacrylate or triethylene glycol diacrylate.
Preferably, the pigment is selected from blue pigments PB15:1, PB15:2, PB15:3, PB15:4, yellow pigments PY138, PY150, PY151, PY155, PY168, PY180, PY185 and PY 194; red pigment PR57:1, PR122, PR146, PR254 and PR269, purple pigment PV19 and black pigment which is at least one of carbon black. The surface anchoring group of the pigment is an aromatic functional group, an acid group or a base group.
Preferably, the auxiliary agent comprises the following components in parts by weight: 0.01-10 parts of multiplying agent and 0.01-5 parts of polymerization inhibitor.
The color paste is added with a multiplying agent (hyper-dispersant), so that the dispersibility and stability of the pigment can be improved.
Preferably, the polymerization inhibitor comprises one or more of hydroquinone, methyl hydroquinone, p-hydroxyanisole, 2-tert-butylhydroquinone, 2, 5-di-tert-butylhydroquinone, p-hydroxyanisole, 2, 6-di-tert-butyl-4-methylphenol, p-tert-butylcatechol, GENORAD 16/18/20/22/23 from RAHN, and S100/110/210/130 from cyante.
A preparation method of UV ink-jet color paste comprises the following steps:
(1) dissolving a grafting dispersant and an auxiliary agent by using a monomer, and adding a pigment for mixing to obtain a pre-dispersion liquid;
(2) and (2) grinding the pre-dispersion liquid obtained in the step (1), filtering, and taking a filtrate to obtain the UV ink-jet color paste.
Preferably, the particle size after grinding in step (2) is 100-200 nm. After filtering, the colloid and the large-particle-size particles can be removed, and the UV ink-jet color paste with stable dispersion is obtained.
The UV ink-jet ink comprises the UV ink-jet color paste.
Compared with the prior art, the invention has the following beneficial effects:
(1) the main chain monomer and the branched chain monomer used in the graft type dispersing agent are common raw materials, and the preparation method is simple, so that the graft type dispersing agent has lower production cost and is 50-70% lower than the price of a commercially available dispersing agent for UV ink;
(2) the graft dispersing agent has excellent dispersing effect, can be used for preparing UV ink-jet color paste and UV ink-jet ink, can prevent the blockage of a printing head and improve the smoothness and the vividness of the ink;
(3) the UV ink-jet ink prepared by the grafted dispersant has good stability, and the performances of dispersibility, dilutability, color paste viscosity, particle size, surface tension and the like of the UV ink-jet ink are kept good after being placed for a long time (aged for 7 days at a high temperature of 60 ℃) in an aging test environment.
Detailed Description
In order to make the technical solutions of the present invention more apparent to those skilled in the art, the following examples are given for illustration. It should be noted that the following examples are not intended to limit the scope of the claimed invention.
Example 1
A preparation method of a graft dispersant SA1 specifically comprises the following steps: introducing protective gas nitrogen into a reaction bottle provided with a condensation reflux device, adding solvents 334g of butanone and 160g of isopropanol, and heating to 70-80 ℃; then mixing 150g of 2-phenoxyethyl acrylate serving as a main chain monomer, 20g of acrylamide and 280g of polyethylene glycol monomethyl ether methacrylate (with the polymerization degree n being 50) serving as a branched macromonomer to obtain a premixed solution A; then mixing and stirring 48g of butanone and 8g of azodiisobutyronitrile serving as an initiator until the mixture is dissolved to obtain a premixed solution B; then slowly adding the premixed liquid A and the premixed liquid B into a reaction bottle at the same time for reaction; after 6 hours of reaction, detecting that the amount of the residual monomer is less than 5 percent, and terminating the reaction to obtain the grafting type dispersant with 45 percent of effective component. Dispersant SA1, having a weight average molecular weight of about 22300, comprises the following structural units:
example 2
A preparation method of a graft dispersant SA2 specifically comprises the following steps: introducing protective gas nitrogen into a reaction bottle provided with a condensing reflux device, adding 341g of ethyl acetate and 160g of isopropanol serving as solvents, and heating to 70-80 ℃; then, 230g of 2-phenoxyethyl acrylate serving as a main chain monomer, 30g of methacrylic acid, 10g of acrylamide and 180g of polyethylene glycol monomethyl ether methacrylate (polymerization degree n is 30) serving as a branched macromonomer are mixed to obtain a premixed solution A; then mixing and stirring 42g of ethyl acetate as a solvent and 7g of azodiisobutyronitrile as an initiator until the ethyl acetate and the azodiisobutyronitrile are dissolved to obtain a premixed solution B; then slowly adding the premixed liquid A and the premixed liquid B into a reaction bottle at the same time for reaction; after 7 hours of reaction, the amount of the residual monomer was determined to be less than 5%, and the reaction was terminated to obtain 45% of an effective amount of graft type dispersant SA 2. Dispersant SA2 has a weight average molecular weight of about 45000, and comprises the following structural units:
example 3
The preparation method of the UV ink-jet red color paste specifically comprises the following steps: 200g of the SA1 grafted dispersant prepared in example 1 and 650g of the monomer 2-phenoxyethyl acrylate are mixed, stirred until the components are completely dissolved, 150g of pigment PR122 is added for mixing, and the mixture is stirred to completely wet the pigment to obtain a pre-dispersion liquid; introducing the pre-dispersion liquid into a sand mill for grinding until the average particle size is 100-200 nm; filtering to remove the colloid and the large-particle-size particles, and obtaining the UV ink-jet red color paste with stable dispersion.
Example 4
The preparation method of the UV ink-jet blue color paste specifically comprises the following steps: 160g of the SA2 grafted dispersant prepared in example 2, 660g of monomer ethoxy ethyl acrylate and 500030 g of Solsperse which is a multiplying agent and is lubrazedly are mixed, stirred until the components are completely dissolved, 150g of pigment PB15:4 is added for mixing, and the mixture is stirred to completely wet the pigment to obtain a pre-dispersion liquid; introducing the pre-dispersion liquid into a sand mill for grinding until the average particle size is 100-200 nm; filtering to remove the colloid and the large-particle-size particles, and obtaining the UV ink-jet blue color paste with stable dispersion.
Example 5
The preparation method of the UV ink-jet black color paste specifically comprises the following steps: 200g of SA1 grafted dispersant prepared in the embodiment, 610g of neopentyl glycol polymethyl ethylene oxide diacrylate monomer, 500035g of Solsperse multiplied by Lubri and 5g of hydroquinone serving as a polymerization inhibitor are mixed, stirred until the components are completely dissolved, 150g of carbon black pigment is added and mixed, and the mixture is stirred until the pigment is completely wetted to obtain pre-dispersion liquid; introducing the pre-dispersion liquid into a sand mill for grinding until the average particle size is 100-200 nm; filtering to remove the colloid and the large-particle-size particles, and obtaining the UV ink-jet black color paste with stable dispersion.
Example 6
The preparation method of the UV ink-jet yellow color paste specifically comprises the following steps: 260g of SA2 graft type dispersant prepared in example 2, 530g of monomer dipropylene glycol diacrylate, 2200057 g of Solsperse as a multiplying agent Lubo and 3g of p-hydroxyanisole as a polymerization inhibitor were mixed, stirred until completely dissolved, 150g of pigment PY150 was added and mixed, and stirred until the pigment was completely wetted to obtain a pre-dispersion liquid; introducing the pre-dispersion liquid into a sand mill for grinding until the average particle size is 100-200 nm; filtering to remove the colloid and the large-particle-size particles, and obtaining the UV ink-jet yellow color paste with stable dispersion.
Comparative example 1
The preparation method of the UV ink-jet yellow color paste specifically comprises the following steps: mixing 140g of sorbitan monolaurate serving as a commercially available dispersant with 710g of dipropylene glycol diacrylate, stirring until the sorbitan monolaurate and the dipropylene glycol diacrylate are completely dissolved, adding 150g of PY150 serving as a pigment for mixing, and stirring to completely wet the pigment to obtain a pre-dispersion liquid; and (3) introducing the pre-dispersion liquid into a sand mill for primary grinding, and filtering to remove colloids and large-particle-size particles to obtain the UV ink-jet yellow color paste.
Product effectiveness testing
The UV ink-jet ink is prepared by adopting the color pastes prepared in the examples 3-6 and the comparative example 1 respectively, and the preparation method comprises the following steps: and mixing 15% of color paste and 85% of tetrahydrofurfuryl acrylate to obtain the UV ink-jet ink.
And (3) testing the performance of the prepared UV ink-jet ink before and after aging, and testing the particle size, viscosity, surface tension and filterability of the UV ink-jet ink. The aging test conditions are that the UV ink-jet ink is aged for 7 days at a high temperature of 60 ℃, and the stability of the UV ink-jet ink can be detected through the aging test. The test results are shown in table 1:
particle size detection, using a British Marvens (Malvern) Nano S90 nanometer particle size analyzer;
viscosity measurement using a Wells cone and plate viscometer, Bohler fly (Brookfield);
surface tension test, adopting a Japanese synergy (KYOWA) CBVP type surface tension meter;
and (4) testing the filterability, namely filtering by adopting a glass fiber filter membrane with the aperture of 1.0 mu m and a PP filter membrane with the aperture of 0.45 mu m.
TABLE 1
Wherein the QC evaluation standard is as follows: the average particle size is 100-200nm, the viscosity is 4-8cp, the surface tension is 30-36dyn/cm, and the filtering property is less than 15min/1 kg; after aging at 60 ℃ for 7 days, the particle size change is less than 10%, the surface tension change is less than 5%, the viscosity change is less than 10%, and the filter filterability is less than 15min/1 kg. If the above judgment standard is met, the product is qualified OK, otherwise, the product is unqualified NG.
As shown in Table 1, compared with the comparative example 1, the UV ink-jet inks prepared by the UV ink-jet color pastes in the examples 3-6 meet the specified requirements on indexes such as average particle size, viscosity, surface tension, filtering property and the like; and can still maintain good performance after being aged for 7 days at the high temperature of 60 ℃, and has better stability.
Claims (8)
1. A graft type dispersant is characterized by being mainly prepared from a main chain monomer, a branched chain monomer, an initiator and a solvent, wherein the mass ratio of the main chain monomer to the branched chain monomer is (1-2) to (1-15);
the main chain monomer comprises a monomer containing an aromatic group and a monomer containing an acid base, and the branched chain monomer is selected from at least one of polyethylene glycol monomethyl ether methacrylate, polyethylene glycol methacrylate, polypropylene glycol monomethyl ether methacrylate or polypropylene glycol methacrylate;
the monomer containing aromatic groups is selected from at least one of 2-phenoxyethyl methacrylate, 2-phenoxyethyl acrylate, polyethylene glycol nonyl phenyl ether acrylate, polypropylene glycol nonyl phenyl ether acrylate or o-phenylphenoxy ethyl acrylate;
the acid-containing base represents at least one of an acid-containing group or a basic group;
the monomer containing acid base is at least one of methacrylic acid, maleic acid, fumaric acid, ethylene sulfonate, styrene sulfonate, ethylene phosphate, methacrylamide, hydroxymethyl acrylamide, hydroxyethyl acrylamide, hydroxypropyl acrylamide, vinyl imidazole, vinyl caprolactam, N-dimethylacrylamide, N-acryloyl morpholine or N-vinyl pyrrolidone.
2. The graft dispersant of claim 1, wherein the degree of polymerization of said branched monomer is 10 to 200.
3. The method for producing a graft dispersant according to any one of claims 1 to 2, comprising the steps of:
(1) mixing a main chain monomer and a branched chain monomer to obtain a premixed solution A; dissolving an initiator by using a solvent to obtain a premixed solution B;
(2) and mixing the premixed solution A and the premixed solution B for reaction under the protective gas environment to obtain the graft type dispersing agent.
4. The method according to claim 3, wherein the reaction temperature in the step (2) is 70 to 80 ℃ and the reaction time is 4 to 7 hours.
5. The UV ink-jet color paste is characterized by comprising the following components in parts by weight:
6. the method for preparing the UV ink-jet color paste according to claim 5, which is characterized by comprising the following steps of:
(1) dissolving a grafting dispersant and an auxiliary agent by using a monomer, and adding a pigment for mixing to obtain a pre-dispersion liquid;
(2) and (2) grinding the pre-dispersion liquid obtained in the step (1), filtering, and taking a filtrate to obtain the UV ink-jet color paste.
7. The UV inkjet color paste according to claim 5, wherein the auxiliary comprises the following components in parts by weight: 0.01-10 parts of multiplying agent and 0.01-5 parts of polymerization inhibitor.
8. A UV inkjet ink comprising the UV inkjet paste according to claim 5.
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| CN114014992B (en) * | 2021-11-12 | 2023-06-23 | 中交第四航务工程局有限公司 | Mutually exclusive/associative polycarboxylate superplasticizer and preparation method and application thereof |
| CN114736560B (en) * | 2022-04-27 | 2023-05-30 | 深圳市华星光电半导体显示技术有限公司 | Printing ink, display panel and preparation method thereof |
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| CN104884538A (en) * | 2012-12-11 | 2015-09-02 | 大日精化工业株式会社 | Pigment dispersant, production method for pigment dispersant, and pigment dispersion liquid |
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| WO2018021119A1 (en) * | 2016-07-26 | 2018-02-01 | 富士フイルム株式会社 | Pigment dispersion and inkjet ink |
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| JP2019056042A (en) * | 2017-09-20 | 2019-04-11 | 富士ゼロックス株式会社 | Pigment dispersant, aqueous pigment dispersion composition, aqueous ink, ink cartridge, recording apparatus, and recording method |
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| CN102993824A (en) * | 2011-09-14 | 2013-03-27 | 中国科学院化学研究所 | UV-curable ink used in inkjet printing direct-to-plate, and preparation method and application thereof |
| CN105073827A (en) * | 2012-02-24 | 2015-11-18 | 巴斯夫欧洲公司 | Novel polymer dispersants |
| CN104884538A (en) * | 2012-12-11 | 2015-09-02 | 大日精化工业株式会社 | Pigment dispersant, production method for pigment dispersant, and pigment dispersion liquid |
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