CN117887009A - Preparation method and application of structure-controllable pigment hyper-dispersant - Google Patents
Preparation method and application of structure-controllable pigment hyper-dispersant Download PDFInfo
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- CN117887009A CN117887009A CN202410074064.XA CN202410074064A CN117887009A CN 117887009 A CN117887009 A CN 117887009A CN 202410074064 A CN202410074064 A CN 202410074064A CN 117887009 A CN117887009 A CN 117887009A
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- pigment
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- hyperdispersant
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- 239000000049 pigment Substances 0.000 title claims abstract description 116
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 68
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 239000000178 monomer Substances 0.000 claims abstract description 35
- 239000006185 dispersion Substances 0.000 claims abstract description 32
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 9
- 238000007614 solvation Methods 0.000 claims abstract 2
- KXYAVSFOJVUIHT-UHFFFAOYSA-N 2-vinylnaphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC=C21 KXYAVSFOJVUIHT-UHFFFAOYSA-N 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 239000012860 organic pigment Substances 0.000 claims description 32
- 238000006116 polymerization reaction Methods 0.000 claims description 22
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 17
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 16
- 239000003999 initiator Substances 0.000 claims description 15
- 239000012629 purifying agent Substances 0.000 claims description 15
- 239000011259 mixed solution Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical compound [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 claims description 11
- 239000012989 trithiocarbonate Substances 0.000 claims description 11
- -1 methoxy alkene ester Chemical class 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 239000012987 RAFT agent Substances 0.000 claims description 3
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical group C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 2
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 claims 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims 1
- XOAMURIABKEBKW-UHFFFAOYSA-N 2-sulfonylpropanoic acid Chemical compound OC(=O)C(C)=S(=O)=O XOAMURIABKEBKW-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 claims 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 claims 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 239000012991 xanthate Substances 0.000 claims 1
- 239000002245 particle Substances 0.000 abstract description 24
- 239000003973 paint Substances 0.000 abstract description 9
- 230000008901 benefit Effects 0.000 abstract description 6
- 238000004873 anchoring Methods 0.000 abstract description 5
- 239000000976 ink Substances 0.000 abstract description 4
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 abstract description 4
- 238000003860 storage Methods 0.000 abstract description 4
- 239000004753 textile Substances 0.000 abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 84
- 229910052757 nitrogen Inorganic materials 0.000 description 42
- 239000007788 liquid Substances 0.000 description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 230000010355 oscillation Effects 0.000 description 16
- 239000000758 substrate Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- 239000002202 Polyethylene glycol Substances 0.000 description 9
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 238000004090 dissolution Methods 0.000 description 9
- 229920001223 polyethylene glycol Polymers 0.000 description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000001291 vacuum drying Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000011345 viscous material Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- QYCVBOXNHNZFKO-UHFFFAOYSA-N ethylideneazanide Chemical compound [CH2]C=[N] QYCVBOXNHNZFKO-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000007792 addition Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 229920005565 cyclic polymer Polymers 0.000 description 2
- 238000006392 deoxygenation reaction Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000005189 flocculation Methods 0.000 description 2
- 230000016615 flocculation Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 229940005605 valeric acid Drugs 0.000 description 2
- 229920003169 water-soluble polymer Polymers 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
- 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
- C08F226/00—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
-
- 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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
-
- 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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention relates to the field of textile auxiliaries, and discloses a preparation method and application of a structure-controllable pigment hyper-dispersant. The pigment hyper-dispersant is prepared by soap-free RAFT polymerization by taking hydrophilic monomers as solvation chain segments and hydrophobic monomers as anchoring chain segments. Compared with the traditional dispersing agent, the pigment dispersing agent has the advantages of controllable structure and molecular weight and the like, and can be suitable for dispersing various pigments. The dispersing agent has large steric hindrance and strong anchoring capability, and the dispersed pigment color paste has excellent dispersion stability and storage stability; meanwhile, the pigment color paste has low viscosity and small particle size. Has wide application prospect in the fields of printing ink, pigment and paint.
Description
Technical Field
The invention relates to the field of textile auxiliaries, in particular to a preparation method and application of a structure-controllable pigment hyper-dispersant.
Background
In recent years, pigments have been increasingly used in the fields of paints, inks, and the like. In contrast to dyes, pigments are usually present in the form of powder or particles, and pigments are not substantially dissolved in aqueous systems, so that when pigments are used in the above fields, aqueous color pastes, which are obtained by dispersing, grinding, centrifuging, washing and other raw materials such as pigments, dispersants, water, zirconium beads and the like, and in which pigment particles are stably dispersed in aqueous systems, are generally used in the form of aqueous pigment dispersions. However, because the particle size of the pigment particles in the aqueous color paste is smaller, and the surface of the pigment particles has larger surface energy, flocculation is easy to occur among the pigment particles, so that the particle size is increased, and the larger particle size has very obvious influence on the application effects of pigment tinting strength, vividness, brightness and the like. The dispersion stability of pigment particles is obviously improved under the action of a high molecular dispersing agent, so that a proper pigment dispersing agent is an important raw material for preparing the aqueous color paste with excellent stability and tinting strength.
Pigments exist mainly in the form of aggregates, agglomerates or floccules, and if the pigment particles are too large, the particle size distribution is uneven, which may result in poor color brightness and vividness of the pigment. The pigment can be used as a colorant, and can well exert the coloring effect only if the pigment is uniformly and stably dispersed in a medium. Commonly used pigment dispersants can be divided into ionic and nonionic ones. Ionic groups can be further divided into cationic, anionic and amphoteric groups. The pigment dispersant is used in the paint, so that the gloss of the paint film can be increased, the leveling property can be improved, the coloring and hiding power of the paint can be improved, the flooding and sedimentation can be prevented, and the production efficiency and the storage stability of the paint can be improved.
Organic pigments are insoluble organic substances that are typically added to a substrate in a highly dispersed state to color the substrate. Organic pigments are widely used for the primary pulp coloration of inks, paints, coatings, synthetic fibers, and for the pigment printing of textiles, the coloration of plastics and rubber leather, and the like. Organic pigments are bright in color, strong in tinting strength, and nontoxic, but are often inferior to inorganic pigments in light, heat, solvent and flame resistance. On the other hand, the particles of the organic pigment are extremely easy to agglomerate, and the dispersibility of the organic pigment has an important influence on the service performance. The study of the dispersibility of organic pigments has been a long-felt and studied hotspot for those skilled in the art. Polyvinylpyrrolidone (PVP) is a nonionic polymer compound, the most distinctive of N-vinyl-amine polymers, and the deepest and most widely studied fine chemicals. PVP is used as a synthetic water-soluble polymer compound, has the general properties, dispersibility and hygroscopicity of the water-soluble polymer compound, but has the most characteristic of excellent dissolution performance and physiological compatibility. The PVP is soluble in water and most of organic solvents in synthetic polymers, has low toxicity and good physiological compatibility, and has wide application prospect in medicines, foods and cosmetics. However, because of their different molecular weights and different dispersibility, designs need to be continually explored.
In view of the above, it is desirable to provide an organic pigment dispersant which can improve the dispersibility, fluidity and tinting strength of an organic pigment, and which can provide an organic pigment system with good thermal stability and improve the gloss and hiding power of a paint after pigment dispersion.
Disclosure of Invention
The invention aims to comprehensively solve the problems of poor pigment dispersing capability, easy flocculation, low tinting strength of color paste, poor storage stability, non-systemization of products, insufficient adhesion of a dispersing agent to a base material and the like of the pigment dispersing agent, and provides a preparation method and application of a structure-controllable pigment hyperdispersing agent. First, a certain amount of solvated segment hydrophilic monomer, anchor segment hydrophobic monomer and macro-RAFT agent are dissolved in a solvent to obtain a mixed solution, and deoxygenation is carried out for a period of time. Subsequently, an amount of initiator is added and reacted for a period of time at a temperature. And (3) purifying after the reaction is finished to obtain a target product.
In order to achieve the above purpose, one technical scheme of the invention is as follows:
the preparation and application of the structure-controllable pigment hyper-dispersant are characterized in that the pigment hyper-dispersant is a solvated chain segment hydrophilic monomer-Co-anchor chain segment hydrophobic monomer polymerized by RAFT, and the technical synthesis process comprises the following specific steps:
(1) First, a certain amount of solvated segment hydrophilic monomer, anchor segment hydrophobic monomer and macro-RAFT agent are dissolved in a solvent to obtain a mixed solution, and deoxygenation is performed for a period of time.
(2) And adding an initiator into the reaction, continuously introducing inert protective gas, transferring to an oil bath at a certain temperature, reacting for a period of time, terminating polymerization in a liquid nitrogen environment after the polymerization reaction is finished, adding a certain amount of purifying agent to purify the reactant, and finally drying the volatilized purifying agent in vacuum to obtain the copolymer.
Preferably, the solvating segment monomer in step (1) is one or more of 2-vinylpyridine, N-vinylpyrrolidone and methoxypolyethylene glycol acrylate.
Preferably, the anchor segment hydrophobic monomer in the step (1) is one or more of styrene (St), 4-vinyl biphenyl (4-VBP) and 2-vinyl naphthalene.
Preferably, the content of the hydrophilic monomer of the solvating chain segment in the step (1) ranges from 4 to 42mmol, and the content of the hydrophobic monomer of the anchoring chain segment ranges from 1 to 4mmol.
Preferably, the initiator in the step (1) is one of azodiisobutyronitrile, 4-azodicyanovaleric acid and benzoyl peroxide.
Preferably, the solvent in the step (1) is one of 1, 4-dioxane, butyl acetate and N, N-dimethylformamide, and the solvent accounts for 80-90% by weight of the total mass of the monomers.
Preferably, the initiator content in the step (1) is 0.05 to 0.2% wt of the total monomer content, more preferably, the initiator is 0.05 to 1% wt of the total mass of the solvated segment monomer and the anchor segment monomer, the chain transfer agent content is in the range of 0.5 to 8mmol, more preferably, the chain transfer agent content is in the range of 0.5 to 3mmol. The content of the vinyl cyclic nitrogen-containing monomer is 2-40 mmol, and the proportion of the monomer in the solvent is kept to be 5-40%.
Preferably, the deoxidation in step (1) is carried out in an inert shielding gas shielding method, preferably nitrogen is used as shielding gas, and the air is aerated for 15-30 min at 25-35 ℃.
Preferably, in the step (2), after the monomer is added, continuously introducing nitrogen into the reactor for 20-35 min, and evacuating oxygen in the reactor to avoid the influence of the oxygen on chemical reaction.
Preferably, in the step (2), the RAFT polymerization reaction temperature is 60-100 ℃, the reaction time is 2-10 hours, more preferably, the RAFT polymerization reaction temperature is 75-85 ℃ and the reaction time is 3-8 hours.
Preferably, the purifying agent added in the step (2) is one or more of anhydrous diethyl ether or n-hexane, which accounts for 150-200% of the total mass of the substrate, and the purifying agent is purified for three times in a liquid nitrogen cooling environment.
Preferably, the prepared liquid dispersing agent in the step (2) is dried in a vacuum oven at 40-50 ℃ for 8-12 hours, and the product is a light yellow viscous substance.
Preferably, the components prepared in step (2) have a degree of polymerization m: n: p=2 to 30:1 to 12:1 to 4.
Wherein:
y is a solvated segment monomer and V is an anchor segment monomer.
The invention also provides application of the pigment dispersing agent in dispersing organic pigment phthalocyanines blue, pigment red 122 and pigment yellow 14.
The invention has the beneficial effects that:
(1) The organic pigment dispersing agent can form anchoring on the surfaces of pigment particles, can enable the dispersing agent and the pigment particles to be stably combined together, and hydrophilic groups of the pigment can form solvated chains to cause steric hindrance among the pigment particles, so that the aggregation of dye particles is effectively prevented.
(2) The vinyl nitrogen-containing cyclic polymer copolymer as the hyper-dispersant can obviously reduce the viscosity of the pigment and improve the gloss and hiding power of the pigment after dispersion, and compared with the hyper-dispersant prepared by RAFT polymerization reaction in the current market, the hyper-dispersant has the advantages of adjustable structure and controllable molecular weight, and the molecular weight has great influence on the dispersion effect, so the design of the dispersing agent with controllable molecular weight has great significance for improving the dispersion effect of the dispersing agent on the organic pigment.
(3) Compared with the traditional dispersing agent, the pigment dispersing agent has the advantages of controllable structure and molecular weight and the like, and can be suitable for dispersing various pigments. The dispersing agent has large steric hindrance and strong anchoring capability, and the dispersed pigment color paste has excellent dispersion stability and storage stability; meanwhile, the pigment color paste has low viscosity and small particle size. Has wide application prospect in the fields of printing ink, pigment and paint. The aqueous pigment color paste obtained by the invention meets the development requirements of green and healthy textiles, not only meets the requirements of good dispersibility and low toxicity of a dispersing agent, but also can uniformly disperse pigment, meets the requirements of modern industrial production of pigment color paste, brings new social benefit and economic benefit, and has great development potential and broad market prospect.
Drawings
FIGS. 1 (a) to (d) are particle diameter diagrams of pigment-dispersing agent-dispersed pigments in the present invention;
FIG. 2 shows NVP according to the present invention 12 -Co-mPEGA 6 Pigment dispersant NMR map;
FIG. 3 shows NVP according to the present invention 12 -Co- (2-vinyl naphthalene) 2 Pigment dispersant NMR map;
FIG. 4 shows NVP according to the present invention 24 -Co-mPEGA 10 -Co- (2-vinyl naphthalene) 2 Pigment dispersant NMR chart.
FIG. 5 shows the structure of BYK-191 and NVP in the present invention 12 -Co-mPEGA 6 、NVP 12 -Co- (2-vinyl naphthalene) 2 、NVP 24 -Co-mPEGA 10 -Co- (2-vinyl naphthalene) 2 Pigment dispersant stability profile of dispersed pigment.
Detailed Description
The following description is only a preferred embodiment of the present invention and is not intended to limit the present invention, but although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that modifications may be made to the technical solutions described in the foregoing embodiments, or equivalents may be substituted for some of the technical features thereof. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
The experiment is a more preferable scheme:
(1) Preparation of (N-vinylpyrrolidone) -Co-methoxypolyethylene glycol acrylate-Co- (2-vinylnaphthalene) copolymer: slowly adding a mixed solution consisting of solvated hydrophilic monomer N-vinyl pyrrolidone, methoxy polyethylene glycol acrylate, anchor chain segment hydrophobic monomer 2-vinyl naphthalene, RAFT reagent trithiocarbonate, pyridine and 1,4 dioxane into a reactor, stirring and introducing nitrogen for a period of time.
(2) Adding 4, 4-azodicarbonyl valeric acid into the reaction, continuously introducing nitrogen, moving to an oil bath at a certain temperature, reacting for a period of time, terminating polymerization in a liquid nitrogen environment after the polymerization reaction is finished, adding a certain amount of purifying agent to purify the reactant, and finally vacuum drying and volatilizing the purifying agent to obtain the vinyl nitrogen-containing annular high polymer copolymer.
The synthetic route of the copolymer obtained by the above reaction is as follows:
(3) Preparation of pigment dispersion.
In order that the above-recited objects, features and advantages of the present invention will become more readily apparent, a more particular description of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings.
The preparation and application of the structure-controllable pigment hyper-dispersant comprise:
step one, preparation of a (N-vinyl pyrrolidone) -Co-methoxy polyethylene glycol acrylate-Co- (2-vinyl naphthalene) random copolymer:
the mixed solution of N-vinyl pyrrolidone and methoxy polyethylene glycol acrylate, 2-vinyl naphthalene and trithiocarbonate of an aluminum peroxide column is taken as a RAFT reagent, a proper amount of pyridine is added to ensure that the reaction pH=3-5, and 1, 4-dioxane is slowly added into a reactor, and the mixed solution is stirred at 25-40 ℃ and nitrogen is introduced for 15-30 min.
And step two, adding an initiator 4, 4-azo dicyanovaleric acid into the reaction, continuously introducing nitrogen, and transferring to an oil bath pot with the temperature of 75-90 ℃.
And (3) reacting for 3-5 h at 75-90 ℃, terminating polymerization in a liquid nitrogen environment after the polymerization reaction is finished, adding n-hexane purification reactant with a substrate accounting for 150-200% of the total mass, and finally drying in a vacuum oven at 35 ℃ for 9-12 h to volatilize the purifying agent to obtain the vinyl nitrogen-containing cyclic polymer random copolymer.
Step three, preparing pigment dispersion liquid:
the prepared dispersant was used to prepare a pigment dispersion according to 20% owf of the organic pigment, phthlish blue.
Pigment dispersant prepared by the above steps
Raw material source description: the reagents used in the examples were purchased from Ala-dine (N-vinylpyrrolidone, methoxypolyethylene glycol acrylate, 2-vinylnaphthalene, 4-azobiscyano valeric acid) and An Naiji (1, 4-dioxane, pyridine) and were analytically pure except that the individual drugs were passed through the column and the drugs passed through the column were identified, and the remaining unexplained drugs were used as they were.
Comparative example 1 (Pick BYK-191 dispersant (Germany))
The prepared dispersing agent is prepared into pigment dispersion liquid according to 20% owf of organic pigment phthalocyanine blue, preferably 0.2g of organic pigment is taken, 40ml of deionized water (pH=8-9) is added, 20% owf of pigment dispersing agent is added, the dispersing agent and pigment are uniformly dispersed in a solvent by ultrasonic oscillation, and then the pigment dispersion liquid is obtained by crushing by a cell crusher.
Example 1 (NVP) 12 -Co-mPEGA 6 )
(NVP 12 -Co-mPEGA 6 ) Preparation of the copolymer: adding a mixed solution consisting of 12mmol of N-vinyl pyrrolidone, 6mmol of mPEGA (methoxypolyethylene glycol acrylate), pyridine (pyridine is added to ensure that the reaction pH=3-5) and 1, 4-dioxane into a reactor with a magnetic rotor, firstly adding into a ultrasonic oscillator (300W), ultrasonic power is 80% for 10min, adding ice blocks during ultrasonic oscillation, maintaining the temperature within a range of 20 ℃ to accelerate dissolution of a reaction substrate, magnetically stirring and introducing nitrogen at the temperature of 25 ℃ and reacting for 15min, continuously introducing nitrogen after the initiator content accounting for 0.2 wt% of the monomer content, 1mmol of trithiocarbonate and 1, 4-dioxane are all added, reacting for 4h at the temperature of 75 ℃, terminating polymerization in a liquid nitrogen environment after the polymerization reaction is finished, adding a certain amount of N-hexane as a purifying agent, wherein the N-hexane is 200% of the total mass of the product, purifying for three times under the liquid nitrogen environment, and finally vacuum drying for 10h at 40 ℃ to obtain a light yellow viscous substance.
The prepared dispersing agent is prepared into pigment dispersion liquid according to 20% owf of organic pigment phthalocyanine blue, preferably 0.2g of organic pigment is taken, 40ml of deionized water (pH=8-9) is added, 20% owf of pigment dispersing agent is added, the dispersing agent and pigment are uniformly dispersed in a solvent by ultrasonic oscillation, and then the pigment dispersion liquid is obtained by crushing by a cell crusher.
Example 2 (NVP) 12 -Co- (2-vinyl naphthalene) 2 )
(NVP 12 -Co- (2-vinyl naphthalene) 2 ) Preparation of the copolymer: adding a mixed solution consisting of 12mmol of N-vinyl pyrrolidone, 2mmol of 2-vinyl naphthalene, pyridine (pyridine is added to ensure the reaction pH=3-5) and 1, 4-dioxane which are subjected to column passing into a reactor with a magnetic rotor, and performing ultrasonic vibrationIn an oscillator (300W), ultrasonic power is 80% for 10min, ice cubes are added during ultrasonic oscillation, the temperature is maintained within 20 ℃ to accelerate dissolution of a reaction substrate, magnetic stirring is carried out at 25 ℃, nitrogen is introduced, reaction is carried out for 15min, the initiator content accounts for 0.2 wt% of the monomer content, 1mmol of trithiocarbonate and 1, 4-dioxane are all added, nitrogen is continuously introduced, reaction is carried out for 4h at 75 ℃, polymerization is terminated in a liquid nitrogen environment after the polymerization reaction is finished, a certain amount of n-hexane which is 200% of the total mass of a product is added, purification is carried out for three times in the liquid nitrogen environment, and finally vacuum drying is carried out at 40 ℃ for 9-12 h, wherein the product is a light yellow viscous substance.
The prepared dispersing agent is prepared into pigment dispersion liquid according to 20% owf of organic pigment phthalocyanine blue, preferably 0.2g of organic pigment is taken, 40ml of deionized water (pH=8-9) is added, 20% owf of pigment dispersing agent is added, the dispersing agent and pigment are uniformly dispersed in a solvent by ultrasonic oscillation, and then the pigment dispersion liquid is obtained by crushing by a cell crusher.
Example 3 (NVP) 6 -Co-mPEGA 2 -Co- (2-vinyl naphthalene) 2 )
(NVP 6 -Co-mPEGA 2 -Co- (2-vinyl naphthalene) 2 ) Preparation of the copolymer: adding a mixed solution consisting of 6mmol of N-vinyl pyrrolidone, 2mmol of methoxy polyethylene glycol acrylic ester, 2mmol of 2-vinyl naphthalene, pyridine (pyridine is added to ensure that the reaction pH=3-5) and 1, 4-dioxane into a reactor with a magnetic rotor, firstly adding into a ultrasonic oscillator (300W), carrying out ultrasonic power of 80% for 10min, adding ice cubes during ultrasonic oscillation, maintaining the temperature within 20 ℃ to accelerate dissolution of a reaction substrate, magnetically stirring and introducing nitrogen at 25 ℃ for 15min, continuously introducing nitrogen after the total addition of the 1mmol of trithiocarbonate and 1, 4-dioxane, reacting for 4h at 75 ℃, adding a certain amount of N-hexane as a purifying agent in a liquid nitrogen environment, purifying three times under a liquid nitrogen drying environment, and finally vacuum drying for 9-12 h at 40 ℃ under a vacuum condition, wherein the content of the product is yellowA color viscous substance.
The prepared dispersing agent is prepared into pigment dispersion liquid according to 20% owf of organic pigment phthalocyanine blue, preferably 0.2g of organic pigment is taken, 40ml of deionized water (pH=8-9) is added, 20% owf of pigment dispersing agent is added, the dispersing agent and pigment are uniformly dispersed in a solvent by ultrasonic oscillation, and then the pigment dispersion liquid is obtained by crushing by a cell crusher.
Example 4 (NVP) 6 -Co-mPEGA 2 -Co- (2-vinyl naphthalene) 4 )
(NVP 6 -Co-mPEGA 2 -Co- (2-vinyl naphthalene) 4 ) Preparation of the copolymer: adding a mixed solution consisting of 6mmol of N-vinyl pyrrolidone, 2mmol of methoxy polyethylene glycol acrylic ester, 4mmol of 2-vinyl naphthalene, pyridine (pyridine is added to ensure that the reaction pH=3-5) and 1, 4-dioxane into a reactor with a magnetic rotor, firstly adding into an ultrasonic oscillator (300W), ultrasonic power is 80% for 10min, adding ice cubes during ultrasonic oscillation, maintaining the temperature within 20 ℃ to accelerate dissolution of a reaction substrate, magnetically stirring and introducing nitrogen at 25 ℃ and reacting for 15min, continuously introducing nitrogen after the initiator content accounting for 0.2 wt% of the monomer content, 1mmol of trithiocarbonate and 1, 4-dioxane are added, reacting for 4h at 75 ℃, terminating polymerization in a liquid nitrogen environment after the polymerization reaction is finished, adding a certain amount of N-hexane as a purifying agent, purifying for three times under the liquid nitrogen environment, and finally vacuum drying at 40 ℃ for 9-12 h under the liquid nitrogen environment to obtain a light yellow sticky substance.
The prepared dispersing agent is prepared into pigment dispersion liquid according to 20% owf of organic pigment phthalocyanine blue, preferably 0.2g of organic pigment is taken, 40ml of deionized water (pH=8-9) is added, 20% owf of pigment dispersing agent is added, the dispersing agent and pigment are uniformly dispersed in a solvent by ultrasonic oscillation, and then the pigment dispersion liquid is obtained by crushing by a cell crusher.
Example 5 (NVP) 12 -Co-mPEGA 6 -Co- (2-vinyl naphthalene) 2 )
(NVP 12 -Co-mPEGA 6 -Co- (2-vinyl naphthalene) 2 ) Preparation of the copolymerThe preparation method comprises the following steps: adding a mixed solution consisting of 12mmol of N-vinyl pyrrolidone, 6mmol of methoxy polyethylene glycol acrylic ester, 2mmol of 2-vinyl naphthalene, pyridine (pyridine is added to ensure that the reaction pH=3-5) and 1, 4-dioxane into a reactor with a magnetic rotor, firstly adding into an ultrasonic oscillator (300W), ultrasonic power is 80% for 10min, adding ice cubes during ultrasonic oscillation, maintaining the temperature within 20 ℃ to accelerate dissolution of a reaction substrate, magnetically stirring and introducing nitrogen at 25 ℃ for 15min, continuously introducing nitrogen after the initiator content accounting for 0.0.2% of the monomer content is added, 1mmol of trithiocarbonate and 1, 4-dioxane are added, stopping the reaction for 4h at 75 ℃ in a constant-temperature oil bath pot after the polymerization reaction, adding a certain amount of N-hexane which is 200% of the total mass of a product, purifying for three times in a liquid nitrogen environment, and finally drying the product in vacuum at 40 ℃ for 12h to obtain a light yellow sticky product.
The prepared dispersing agent is prepared into pigment dispersion liquid according to 20% owf of organic pigment phthalocyanine blue, preferably 0.2g of organic pigment is taken, 40ml of deionized water (pH=8-9) is added, 20% owf of pigment dispersing agent is added, the dispersing agent and pigment are uniformly dispersed in a solvent by ultrasonic oscillation, and then the pigment dispersion liquid is obtained by crushing by a cell crusher.
Example 6 (NVP) 12 -Co-mPEGA 6 -Co- (2-vinyl naphthalene) 4 )
(NVP 12 -Co-mPEGA 6 -Co- (2-vinyl naphthalene) 4 ) Preparation of the copolymer: adding a mixed solution consisting of 12mmol of N-vinyl pyrrolidone, 6mmol of methoxy polyethylene glycol acrylate, 4mmol of 2-vinyl naphthalene, pyridine (pyridine is added to ensure that the reaction pH=3-5) and 1, 4-dioxane into a reactor with a magnetic rotor, firstly adding into a supersonic vibrator (300W), wherein the supersonic power is 80% for 10min, adding ice blocks during supersonic vibration, maintaining the temperature within 20 ℃ to accelerate the dissolution of a reaction substrate, magnetically stirring and introducing nitrogen at 25 ℃ to react for 15min, wherein the initiator content accounts for 0.2 wt% of the monomer content, 1mmol of trithiocarbonate and 1, 4-dioxane are all addedThen, continuously introducing nitrogen, reacting for 4 hours at the temperature of 75 ℃, terminating the polymerization in a liquid nitrogen environment after the polymerization reaction is finished, adding a certain amount of purifying agent n-hexane, wherein the n-hexane is 200% of the total mass of the product, purifying for three times in the liquid nitrogen environment, and finally vacuum drying for 12 hours at the temperature of 40 ℃, wherein the product is a yellowish viscous substance.
The prepared dispersing agent is prepared into pigment dispersion liquid according to 20% owf of organic pigment phthalocyanine blue, preferably 0.2g of organic pigment is taken, 40ml of deionized water (pH=8-9) is added, 20% owf of pigment dispersing agent is added, the dispersing agent and pigment are uniformly dispersed in a solvent by ultrasonic oscillation, and then the pigment dispersion liquid is obtained by crushing by a cell crusher.
Example 7 (NVP) 24 -Co-mPEGA 10 -Co- (2-vinyl naphthalene) 2 )
(NVP 24 -Co-mPEGA 10 -Co- (2-vinyl naphthalene) 2 ) Preparation of the copolymer: adding a mixed solution consisting of 24mmol of N-vinyl pyrrolidone, 10mmol of methoxy polyethylene glycol acrylic ester, 2mmol of 2-vinyl naphthalene, pyridine (pyridine is added to ensure that the reaction pH=3-5) and 1, 4-dioxane into a reactor with a magnetic rotor, firstly adding into an ultrasonic oscillator (300W), carrying out ultrasonic power of 80% for 10min, adding ice cubes during ultrasonic oscillation, maintaining the temperature within a range of 20 ℃ to accelerate the dissolution of a reaction substrate, magnetically stirring and introducing nitrogen at the temperature of 25 ℃ and reacting for 15min, continuously introducing nitrogen after the initiator content accounting for 0.2 wt% of the monomer content, 1mmol of trithiocarbonate and 1, 4-dioxane are all added, reacting for 4h at the temperature of 75 ℃, terminating polymerization in a liquid nitrogen environment after the polymerization reaction, adding a certain amount of N-hexane as a purifying agent, carrying out purification three times under the liquid nitrogen environment, and finally carrying out vacuum drying at 40 ℃ for 12h under the condition that the N-hexane is a light yellow sticky substance.
The prepared dispersing agent is prepared into pigment dispersion liquid according to 20% owf of organic pigment phthalocyanine blue, preferably 0.2g of organic pigment is taken, 40ml of deionized water (pH=8-9) is added, 20% owf of pigment dispersing agent is added, the dispersing agent and pigment are uniformly dispersed in a solvent by ultrasonic oscillation, and then the pigment dispersion liquid is obtained by crushing by a cell crusher.
Example 8 (NVP) 24 -Co-mPEGA 10 -Co- (2-vinyl naphthalene) 4 )
Preparation of (N-vinylpyrrolidone) -Co-methoxypolyethylene glycol acrylate-Co- (2-vinylnaphthalene) copolymer: adding a mixed solution consisting of 24mmol of N-vinyl pyrrolidone, 10mmol of methoxy polyethylene glycol acrylic ester, 4mmol of 2-vinyl naphthalene, pyridine (pyridine is added to ensure that the reaction pH=3-5) and 1, 4-dioxane into a reactor with a magnetic rotor, firstly adding into an ultrasonic oscillator (300W), carrying out ultrasonic power of 80% for 10min, adding ice cubes during ultrasonic oscillation, maintaining the temperature within a range of 20 ℃ to accelerate the dissolution of a reaction substrate, magnetically stirring and introducing nitrogen at the temperature of 25 ℃, then reacting for 15min, continuously introducing nitrogen after the initiator content accounting for 0.2 wt% of the monomer content, 1mmol of trithiocarbonate and 1, 4-dioxane are all added, reacting for 4h at the temperature of 75 ℃, terminating polymerization in a liquid nitrogen environment after the polymerization reaction, adding a certain amount of N-hexane as a purifying agent, carrying out purification three times under the liquid nitrogen environment, and finally carrying out vacuum drying at 40 ℃ for 12h under the condition that the N-hexane is a light yellow sticky substance.
The prepared dispersing agent is prepared into pigment dispersion liquid according to 20% owf of organic pigment phthalocyanine blue, preferably 0.2g of organic pigment is taken, 40ml of deionized water (pH=8-9) is added, 20% owf of pigment dispersing agent is added, the dispersing agent and pigment are uniformly dispersed in a solvent by ultrasonic oscillation, and then the pigment dispersion liquid is obtained by crushing by a cell crusher.
FIG. 1 is a graph showing the particle size distribution of hyperdispersant-dispersed pigments of different structures, which were individually sampled and diluted 1000-fold after passing through the same grinding process, and their particle sizes were measured on a Zetasizer Nano S Particle Size Analyzer (Malvern, britain) instrument. Fig. 2, 3 and 4 are characterization graphs of hyperdispersants of different structures, and fig. 5 is a graph of stability without hyperdispersants of structures. We have determined by examples 1 to 8 that the hyperdispersant has the structure NVP 24 -Co-mPEGA 10 -Co- (2-vinyl naphthalene) 2 Has the best dispersing effect on NVP 12 -Co-mPEGA 6 、NVP 12 -Co- (2-vinyl naphthalene) 2 、NVP 24 -Co-mPEGA 10 -Co- (2-vinyl naphthalene) 4 The hyperdispersant with three structures is characterized, and the hyperdispersant is shown in figures 2, 3 and 4 1 H NMR spectrum. The dispersion effect is also different due to the different structures of the hyperdispersant, and finally the particle sizes of the dispersed pigments are different, as shown in figure 1.
FIG. 5 is BYK-191, NVP 12 -Co-mPEGA 6 、NVP 12 -Co- (2-vinyl naphthalene) 2 、NVP 24 -Co-mPEGA 10 -Co- (2-vinyl naphthalene) 2 Sampling four hyperdispersants with different structures under the same condition (test conditions are all 60 ℃ and observed for 5 days) to obtain a particle size data graph, and finally obtaining NVP 24 -Co-mPEGA 10 -Co- (2-vinyl naphthalene) 2 The dispersion stability of the hyperdispersant is best.
The foregoing preferred embodiments are provided to illustrate and explain the present invention and are not to be construed as limiting the present invention. Although the present invention has been described in detail by the inventor, it will be apparent to those skilled in the art from the disclosure of the summary and examples that various modifications and/or additions or substitutions can be made to the described embodiments and these can achieve the technical effects of the invention and therefore will not be described in detail herein. The terminology presented herein is for the purpose of describing and understanding the technical aspects of the invention and is not intended to be limiting of the invention.
Claims (10)
1. The preparation method of the structure-controllable pigment hyper-dispersant is characterized by comprising the following steps:
firstly, dissolving N-vinyl pyrrolidone, a solvation chain segment hydrophilic monomer, an anchor chain segment hydrophobic monomer and a macro-RAFT reagent in a solvent to obtain a mixed solution, deoxidizing, then adding an initiator, reacting, and purifying after the reaction is finished to obtain the structure-controllable pigment hyperdispersant.
2. The method for preparing the structure-controllable pigment hyperdispersant according to claim 1, wherein the solvating segment hydrophilic monomer is one or more of 2-vinyl pyridine, N-vinyl carbazole and methoxy alkene ester.
3. The method for preparing the structure-controllable pigment hyperdispersant according to claim 1, wherein the methoxyene ester has a structure of formula (I), and the polymerization degree x is 5-10:
4. the method for preparing the structure-controllable pigment hyperdispersant according to claim 1, wherein the hydrophobic monomer of the anchor chain segment is one or more of styrene, 4-vinyl biphenyl and 2-vinyl naphthalene.
5. The method for preparing the structure-controllable pigment hyperdispersant according to claim 1, wherein the macro-RAFT agent is one or more of trithiocarbonate, xanthate, (2-carboxyethyl) sulfonyl thio-carboglycosyl sulfonyl propionic acid and dithiocarbonate;
the initiator is one or more of azodiisobutyronitrile, 4-azodicyanovaleric acid, benzoyl peroxide, dicumyl peroxide and tert-butyl peroxybenzoate.
6. The method for preparing the structure-controllable pigment hyperdispersant according to claim 1, wherein the solvent is one or more of 1, 4-dioxane, butyl acetate, tetrahydrofuran, and N, N-dimethylformamide.
7. The method for preparing the structure-controllable pigment hyperdispersant according to claim 1, wherein the reaction conditions are as follows: the reaction temperature is 60-100 ℃ and the reaction time is 2-10 h.
8. The method for preparing the structure-controllable pigment hyperdispersant according to claim 1, wherein the purification specifically comprises: purifying the reacted product by using a purifying agent, putting the purified polymer into a vacuum oven, and drying for 2-24 hours at 30-60 ℃ to obtain the structure-controllable pigment hyper-dispersant;
the purifying agent is one or more of anhydrous diethyl ether, n-hexane, cyclohexane and dichloromethane.
9. The method for preparing the structure-controllable pigment hyperdispersant according to claim 1, wherein the structure-controllable pigment hyperdispersant has the following structure:
wherein Y is a solvated chain segment monomer, V is an anchor chain segment monomer, and the polymerization degree m: n: p=2 to 30:1 to 12:1 to 4.
10. Use of a structure-controllable pigment hyperdispersant prepared according to the preparation method of any one of claims 1 to 9 in the preparation of an organic pigment dispersion.
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