CN113004458A - Three-component acrylate dispersant and preparation method thereof, and organic pigment color paste and preparation method thereof - Google Patents
Three-component acrylate dispersant and preparation method thereof, and organic pigment color paste and preparation method thereof Download PDFInfo
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- CN113004458A CN113004458A CN202110235360.XA CN202110235360A CN113004458A CN 113004458 A CN113004458 A CN 113004458A CN 202110235360 A CN202110235360 A CN 202110235360A CN 113004458 A CN113004458 A CN 113004458A
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- monomer
- organic pigment
- dispersant
- solvent
- mixing
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- 239000002270 dispersing agent Substances 0.000 title claims abstract description 90
- 239000012860 organic pigment Substances 0.000 title claims abstract description 71
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000000178 monomer Substances 0.000 claims abstract description 127
- 125000003118 aryl group Chemical group 0.000 claims abstract description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 37
- 238000000227 grinding Methods 0.000 claims abstract description 26
- 239000006185 dispersion Substances 0.000 claims abstract description 23
- 239000003999 initiator Substances 0.000 claims description 69
- 239000002904 solvent Substances 0.000 claims description 41
- 238000002156 mixing Methods 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 238000006116 polymerization reaction Methods 0.000 claims description 32
- 239000007788 liquid Substances 0.000 claims description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 10
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- RBFPEAGEJJSYCX-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CCOCCOCCOCCOC(=O)C(C)=C RBFPEAGEJJSYCX-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 5
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 5
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 5
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 5
- -1 methyl dicyclopentenyl acrylate Chemical compound 0.000 claims description 5
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims description 5
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 5
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 claims description 3
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000032683 aging Effects 0.000 abstract description 9
- 238000001179 sorption measurement Methods 0.000 abstract description 3
- 238000005411 Van der Waals force Methods 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000002245 particle Substances 0.000 description 27
- 239000000049 pigment Substances 0.000 description 18
- 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 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 239000002612 dispersion medium Substances 0.000 description 6
- 239000000084 colloidal system Substances 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 5
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000013557 residual solvent Substances 0.000 description 3
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000004873 anchoring Methods 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 229940005605 valeric acid Drugs 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- DTCCVIYSGXONHU-CJHDCQNGSA-N (z)-2-(2-phenylethenyl)but-2-enedioic acid Chemical compound OC(=O)\C=C(C(O)=O)\C=CC1=CC=CC=C1 DTCCVIYSGXONHU-CJHDCQNGSA-N 0.000 description 1
- SSOZBCCITNPUMJ-UHFFFAOYSA-N 1-methoxycyclohexan-1-ol Chemical compound COC1(O)CCCCC1 SSOZBCCITNPUMJ-UHFFFAOYSA-N 0.000 description 1
- CVEPFOUZABPRMK-UHFFFAOYSA-N 2-methylprop-2-enoic acid;styrene Chemical compound CC(=C)C(O)=O.C=CC1=CC=CC=C1 CVEPFOUZABPRMK-UHFFFAOYSA-N 0.000 description 1
- KHJIBKHJFRUMLO-UHFFFAOYSA-N 5-butyl-5-ethoxynonane Chemical compound CCCCC(CCCC)(CCCC)OCC KHJIBKHJFRUMLO-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- LFZDEAVRTJKYAF-UHFFFAOYSA-L barium(2+) 2-[(2-hydroxynaphthalen-1-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Ba+2].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21.C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 LFZDEAVRTJKYAF-UHFFFAOYSA-L 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000008096 xylene Substances 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/282—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing two or more oxygen atoms
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
The invention relates to the technical field of organic pigment color paste, and provides a three-component acrylate dispersing agent and a preparation method thereof, and organic pigment color paste and a preparation method thereof. The invention uses hydrophilic monomer, lipophilic monomer and monomer containing aromatic ring or heterocycle as raw materials to prepare the dispersant, the obtained dispersant contains aromatic ring or heterocycle structure, van der Waals force and large pi bond acting force between aromatic (hetero) group exist between aromatic ring or heterocycle structure in the dispersant and aromatic ring or heterocycle structure in the organic pigment, thus leading the adsorption of the dispersant on the surface of the organic pigment to be firmer and leading the dispersion of the organic pigment to be more stable. The organic pigment color paste prepared by the dispersant can stably disperse the organic pigment, improve the grinding efficiency of the color paste and reduce the grinding time. The invention also provides the organic pigment color paste which has good stability and good aging resistance.
Description
Technical Field
The invention relates to the technical field of organic pigment color paste, in particular to a three-component acrylate dispersing agent and a preparation method thereof, and organic pigment color paste and a preparation method thereof.
Background
The organic pigment is an important chemical raw material and has wide application in the aspects of coatings, paints, printing inks and the like. However, organic pigment particles have small particle size, large specific surface area and high surface energy, and in order to reduce the surface energy and achieve a stable state, the pigment particles mostly exist in an aggregated state, so that a layering phenomenon occurs in a production process, and the properties such as color and luster, transparency and the like are further influenced. Therefore, the dispersion stability of the pigment in the application process is important, and the dispersibility of the organic pigment refers to the condition that the particle size and viscosity of the pigment and the concentration of a dispersion medium are kept stable in the environment of the dispersion medium.
The pigment dispersion is divided into three steps of wetting, mechanical crushing and dispersion stabilization. The wetting of the pigment is related to the dispersant, the organic pigment is a nonpolar molecule and is difficult to disperse in a solution, the dispersant is composed of an anchoring group and a solvating segment, the anchoring group on the dispersant is adsorbed on the surface of the pigment to form an adsorption layer, and the solvating segment is stretched in a solvent to provide steric hindrance or the function of dispersing charges to prevent the agglomeration of pigment particles. At present, common organic pigment dispersants are sodium polyacrylate, styrene-maleic acid half-ester, styrene- (methyl) acrylic acid (ester) copolymer and the like, but the dispersants are difficult to be firmly adsorbed on the surface of the organic pigment, the dispersing performance of the organic pigment dispersants still needs to be improved, when the dispersants are used for preparing color paste, long-time grinding is needed to meet the requirement on the particle size, and the stability of the obtained color paste is poor.
Disclosure of Invention
In view of the above, the invention aims to provide a three-component acrylate dispersant and a preparation method thereof, and an organic pigment color paste and a preparation method thereof. The three-component acrylate dispersing agent provided by the invention can be firmly adsorbed on the surface of an organic pigment, the dispersion stability is high, and the grinding time of the color paste can be reduced and the stability of the organic pigment color paste can be improved by using the three-component acrylate dispersing agent to prepare the organic pigment color paste.
In order to achieve the above object, the present invention provides the following technical solutions:
a three-component acrylate dispersant is prepared from the following components in parts by mass: 5-30% of lipophilic monomer, 5-50% of hydrophilic monomer, 5-20% of monomer containing aromatic ring or heterocycle, 1-10% of initiator and 30-60% of solvent; at least one of the hydrophilic monomer and the lipophilic monomer is an acrylate monomer; the number average molecular weight of the three-component acrylate dispersing agent is 10000-30000, and the weight average molecular weight is 10000-30000.
Preferably, the lipophilic monomer comprises one or more of methyl dicyclopentenyl acrylate, n-butyl acrylate, ethoxy triethylene glycol methacrylate, 2-phenoxyethyl methacrylate, vinyl pyrrolidone and phenoxyethyl acrylate;
the hydrophilic monomer comprises one or more of maleic anhydride, acrylic acid, methacrylic acid, allyl alcohol polyoxyethylene ether, ethylene glycol dimethacrylate and ethoxy triethylene glycol methacrylate;
the aromatic ring in the monomer containing the aromatic ring or the heterocycle is a benzene ring, and the heterocycle is an aromatic heterocycle.
Preferably, the aromatic ring or heterocyclic ring-containing monomer comprises one or more of benzyl methacrylate, tetrahydrofurfuryl methacrylate, methyl styrene, phenyl methacrylate, vinyl toluene and p-methyl styrene.
Preferably, the initiator is an azo compound; the solvent comprises one or more of water, ketone solvent, alcohol solvent, ester solvent and benzene solvent.
Preferably, the ratio of the weight average molecular weight to the number average molecular weight of the three-component acrylate dispersant is 1-2: 1.
The invention provides a preparation method of a three-component acrylate dispersing agent in the scheme, which comprises the following steps:
mixing a lipophilic monomer, a hydrophilic monomer, a monomer containing aromatic rings or heterocyclic rings, an initiator and a solvent for polymerization reaction to obtain the three-component acrylate dispersing agent.
Preferably, the mixing to effect polymerization comprises:
mixing part of hydrophilic monomer, part of lipophilic monomer and part of monomer containing aromatic ring or heterocycle to obtain a first mixed monomer; mixing the residual hydrophilic monomer, the residual lipophilic monomer and the residual monomer containing aromatic ring or heterocycle to obtain a second mixed monomer;
mixing part of the initiator with the first part of the solvent to obtain a first initiator solution, and mixing the rest of the initiator with the second part of the solvent to obtain a second initiator solution;
mixing the first mixed monomer with the rest solvent, and carrying out a first polymerization reaction under the protection of inert gas to obtain a first polymerization reaction feed liquid; mixing the first initiator solution, the second mixed monomer and the first reaction feed liquid, and carrying out a second polymerization reaction to obtain a second reaction feed liquid; and adding the second initiator solution into the second reaction solution to terminate the reaction.
Preferably, the temperature of the first polymerization reaction and the temperature of the second polymerization reaction are independently 70-90 ℃, the time of the first polymerization reaction is 30-40 min, and the time of the second polymerization reaction is 1-2 h.
The invention also provides organic pigment color paste which comprises the following components in percentage by mass: 10-40% of a dispersing agent, 15-40% of an organic pigment and 20-80% of a dispersing medium; the dispersant is the three-component acrylate dispersant described in the above scheme or the three-component acrylate dispersant prepared by the preparation method described in the above scheme; the organic pigment is an organic pigment containing an aromatic ring or a heterocyclic ring.
The invention provides a preparation method of the organic pigment color paste, which comprises the following steps:
mixing a dispersing agent, an organic pigment and a dispersing medium to obtain a pre-dispersion liquid;
and grinding the pre-dispersion liquid and filtering to obtain the organic pigment color paste.
The invention provides a three-component acrylate dispersant, which is prepared from the following components in percentage by mass: 5-30% of lipophilic monomer, 5-50% of hydrophilic monomer, 5-20% of monomer containing aromatic ring or heterocycle, 1-10% of initiator and 30-60% of solvent; at least one of the hydrophilic monomer and the lipophilic monomer is an acrylate monomer. The invention uses hydrophilic monomer, lipophilic monomer and monomer containing aromatic ring or heterocycle as raw materials to prepare the dispersant, the obtained dispersant contains aromatic ring or heterocycle structure, van der Waals force exists between the aromatic ring or heterocycle structure in the dispersant and the aromatic ring or heterocycle structure in the organic pigment and large pi bond acting force exists between aromatic (hetero) groups, thus leading the adsorption of the dispersant on the surface of the organic pigment to be firmer and leading the dispersion of the organic pigment to be more stable. The organic pigment color paste prepared by the dispersant can stably disperse the organic pigment, improve the grinding efficiency of the color paste and reduce the grinding time.
In addition, the dispersing agent provided by the invention has reasonable molecular weight distribution, is not easy to generate winding due to overhigh molecular weight to cause sedimentation, and is not easy to generate flocculation due to insufficient steric hindrance caused by overlow molecular weight of the dispersing agent.
The invention also provides organic pigment color paste which comprises the following components in percentage by mass: 10-40% of three-component acrylate dispersant, 15-40% of organic pigment and 20-80% of dispersion medium. The color paste provided by the invention has good stability and good aging resistance. The results of the examples show that the viscosity and the particle size of the organic pigment paste are not substantially changed after aging for 10 days.
Detailed Description
The invention provides a three-component acrylate dispersant, which is prepared from the following components in percentage by mass: 5-30% of lipophilic monomer, 5-50% of hydrophilic monomer, 5-20% of monomer containing aromatic ring or heterocycle, 1-10% of initiator and 30-60% of solvent, wherein the lipophilic monomer is preferably prepared from the following components in percentage by mass: 10-25% of lipophilic monomer, 10-40% of hydrophilic monomer, 10-15% of monomer containing aromatic ring or heterocycle, 3-5% of initiator and 40-50% of solvent; at least one of the hydrophilic monomer and the lipophilic monomer is an acrylate monomer; the number average molecular weight of the three-component acrylate dispersing agent is 10000-30000, and the weight average molecular weight is 10000-30000.
In the present invention, the lipophilic monomer preferably includes one or more of methyl dicyclopentenyl acrylate, n-butyl acrylate, ethoxy triethylene glycol methacrylate, 2-phenoxyethyl methacrylate, vinyl pyrrolidone and phenoxyethyl acrylate.
In the present invention, the hydrophilic monomer preferably includes one or more of maleic anhydride, acrylic acid, methacrylic acid, allyl alcohol polyoxyethylene ether, ethylene glycol dimethacrylate and ethoxytriethylene glycol methacrylate.
In the present invention, the aromatic ring in the monomer containing aromatic ring or heterocyclic ring is preferably a benzene ring, the heterocyclic ring is preferably an aromatic heterocyclic ring, and more preferably a furan ring, and specifically, the monomer containing aromatic ring or heterocyclic ring preferably includes one or more of benzyl methacrylate, tetrahydrofurfuryl methacrylate, methyl styrene, phenyl methacrylate, vinyl toluene and p-methyl styrene.
In the present invention, the initiator is preferably an azo compound, and more preferably one or more of azobisisoheptonitrile, azobisisobutyronitrile formamide, azobisisobutyrimidazoline hydrochloride, azobiscyclohexylcarbonitrile, and azobiscyanovaleric acid.
In the invention, the solvent preferably comprises one or more of water, ketone solvent, alcohol solvent, ester solvent and benzene solvent; the ketone solvent is preferably one or more of butanone, methyl isobutyl ketone and cyclohexanone; the ester solvent is preferably ethyl acetate and/or isopropyl acetate; the benzene-based solvent is preferably xylene.
In the invention, the number average molecular weight of the three-component acrylate dispersant is 10000-30000, preferably 15000-25000, the weight average molecular weight is 10000-30000, preferably 15000-25000, and the ratio of the weight average molecular weight to the number average molecular weight is preferably 1-2: 1, more preferably 1.1-1.5: 1; the molecular weight of the three-component acrylate is controlled within the range, so that the molecular weight distribution of the dispersing agent is reasonable, the phenomenon that the dispersing agent is wound due to overhigh molecular weight to cause sedimentation is not easy to occur, and the phenomenon that the dispersing agent is flocculated due to insufficient steric hindrance caused by overlow molecular weight is not easy to occur.
The invention also provides a preparation method of the three-component acrylate dispersant, which is characterized by comprising the following steps:
mixing a lipophilic monomer, a hydrophilic monomer, a monomer containing aromatic rings or heterocyclic rings, an initiator and a solvent for polymerization reaction to obtain the three-component acrylate dispersing agent.
In the present invention, the mixing for polymerization preferably comprises:
mixing part of hydrophilic monomer, part of lipophilic monomer and part of monomer containing aromatic ring or heterocycle to obtain a first mixed monomer; mixing the residual hydrophilic monomer, the residual lipophilic monomer and the residual monomer containing aromatic ring or heterocycle to obtain a second mixed monomer;
mixing part of the initiator with the first part of the solvent to obtain a first initiator solution, and mixing the rest of the initiator with the second part of the solvent to obtain a second initiator solution;
mixing the first mixed monomer and the residual solvent, carrying out a first polymerization reaction under the protection of inert gas to obtain a first polymerization reaction feed liquid, mixing the first initiator solution, the second mixed monomer and the first polymerization reaction feed liquid, and carrying out a second polymerization reaction to obtain a second polymerization reaction feed liquid; and adding a second initiator solution into the second polymerization feed liquid to terminate the reaction.
The preparation method of the first mixed monomer, the second mixed monomer, the first initiator solution and the second initiator solution has no special requirement, and the method known by the technical personnel in the field can be adopted. In the invention, in the first initiator solution and the second initiator solution, the mass ratio of the initiator to the solvent is preferably 0.1-0.5: 1 independently; the mass ratio of the initiators in the first initiator solution and the second initiator solution is preferably 2.7-3.2: 1; the amount of the monomers in the first mixed monomer and the second mixed monomer is not particularly required, and any proportion of the monomers can be adopted for preparation, in a specific embodiment of the invention, the amount of the lipophilic monomer in the first mixed monomer is preferably 10-40% of the total mass of the lipophilic monomer, preferably 15-35%, the amount of the hydrophilic monomer is preferably 10-40% of the total mass of the hydrophilic monomer, preferably 15-35%, and the amount of the monomer containing the aromatic ring or the heterocyclic ring is preferably 10-30% of the total mass of the monomer containing the aromatic ring or the heterocyclic ring, preferably 15-20%.
According to the invention, a first mixed monomer and the residual solvent are mixed, and a first polymerization reaction is carried out under the protection of inert gas, so as to obtain a reaction feed liquid. In the invention, the mass ratio of the first mixed monomer to the residual solvent is preferably 0.1-0.8: 1; the temperature of the first polymerization reaction is preferably 70-90 ℃, preferably 75-85 ℃, and the time of the first polymerization reaction is preferably 30-40 min, and more preferably 33-35 min.
After the first reaction is completed, the present invention preferably mixes the first initiator solution, the second mixed monomer and the first polymerization reaction solution for the second polymerization reaction. According to the invention, a first initiator solution and a second mixed monomer are preferably added into a first reaction feed liquid at a certain flow rate, specifically, the flow rate of the first initiator solution is preferably 0.3-0.6 mL/min, more preferably 0.32-0.56 mL/min, and the flow rate of the second mixed monomer is preferably 0.8-2.2 mL/min, more preferably 0.98-2.06 mL/min; the temperature of the second reaction is preferably 70-90 ℃, preferably 75-85 ℃, the time of the second reaction is preferably 1-2 hours, more preferably 1.3-1.5 hours, and the time of the second reaction is counted from the end of adding the first initiator solution and the second mixed monomer. The invention preferably carries out the reaction of the monomers in two parts, the first part of the monomers and the main initiator carry out the polymerization reaction, and the second part of the monomers cause the polymer to grow up, thereby meeting the requirement of molecular weight.
After the second reaction is finished, adding a second initiator solution into the second reaction feed liquid to terminate the reaction. In the invention, the adding speed of the second initiator is preferably 8-12 mL/min, and more preferably 9-10 mL/min. According to the invention, a second initiator solution is added to enable the initiator to react with an unreacted initiator in a system, so that the initiator loses activity and the polymer is prevented from continuously growing, thereby forming a stable molecule of the polymer; in the specific embodiment of the invention, the reaction is continued for 40-60 min after the second initiator solution is added, and the reaction end point can be reached.
After the reaction is finished, the obtained product liquid is a three-component acrylate dispersant solution which can be directly used without any treatment; in the invention, the mass fraction of the three-component acrylate dispersant in the product liquid is preferably 40-60%, and more preferably 50%.
The invention also provides organic pigment color paste which comprises the following components in percentage by mass: 10-40% of dispersing agent, 15-40% of organic pigment and 20-80% of dispersing medium.
The organic pigment color paste provided by the invention comprises 10-40% by mass of a dispersing agent, and preferably 20-30%. In the invention, the dispersant is the three-component acrylate dispersant described in the above scheme or the three-component acrylate dispersant prepared by the preparation method described in the above scheme, and details are not repeated herein; in the invention, the mass of the dispersant is calculated by the mass of the three-component acrylate dispersant solution (namely, product feed liquid) prepared by the scheme.
The organic pigment color paste provided by the invention comprises 15-40% by mass of organic pigment, and preferably 20-35% by mass of organic pigment. In the present invention, the organic pigment is preferably an organic pigment containing a benzene ring or a heterocyclic ring, and the heterocyclic ring is preferably an aromatic heterocyclic ring, specifically, one or more of c.i. pigment yellow 185, c.i. pigment yellow 98, c.i. pigment orange 24, c.i. pigment red 9, c.i. pigment red 12, c.i. pigment violet 3, and c.i. pigment violet 15.
The organic pigment color paste provided by the invention comprises 20-80% of a dispersion medium by mass fraction, and preferably 30-70% of the dispersion medium by mass fraction. In the invention, the dispersion medium is preferably one or more of water, an ether solvent, an ester solvent, a ketone solvent and an alcohol solvent; the ether solvent is preferably one or more of diethyl ether, anisole, isopropyl ether, cyclohexanediol monomethyl ether and tributyl methyl ethyl ether, the ester solvent is preferably one or more of ethyl acetate, isobutyl acetate, propyl acetate, ethyl formate and amyl acetate, the ketone solvent is preferably one or more of acetone, butanone, methyl ethyl ketone, methyl isopropyl ketone and cyclohexanone, and the alcohol solvent is preferably one or more of ethanol, isopropanol, methanol, amyl alcohol and butanol.
The invention also provides a preparation method of the organic pigment color paste, which comprises the following steps:
mixing a dispersing agent, an organic pigment and a dispersing medium to obtain a pre-dispersion liquid;
and grinding the pre-dispersion liquid and filtering to obtain the organic pigment color paste.
The invention has no special requirements on the mixing method, and can uniformly mix the dispersing agent, the organic pigment and the dispersing medium.
In the present invention, the grinding is preferably carried out in a sander; the grinding time is preferably 40-70 min, more preferably 60min, and in the specific embodiment of the invention, the grinding time of the color paste with unit mass is preferably 6-11 g/min; the invention removes colloid and large granular solid in the grinding slurry by filtering; the average particle size of the organic pigment color paste obtained after grinding is preferably 20-150 nm, and more preferably 30-110 nm.
In the invention, the dispersant can fully break up the acting force among the particles in the grinding process, and the particles are uniformly coated, so that the ground particles are not agglomerated and have good fluidity.
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
(1) 36.99g of 2-phenoxyethyl acrylate, 9.82g of acrylic acid and 22.38g of benzyl methacrylate are mixed to obtain a first mixed monomer, the first mixed monomer and 370g of solvent dipropylene glycol are added into a reaction vessel with condensation reflux, nitrogen is introduced and stirring is carried out continuously, and the temperature is increased to 75 ℃;
(2) dissolving 24.00g of azobisisobutyronitrile into 120g of isopropanol to obtain a first initiator solution, stirring and mixing 209.65g of 2-phenoxyethyl acrylate, 55.65g of acrylic acid and 89.50g of benzyl methacrylate to obtain a second mixed monomer, and after the temperature in the step (1) is raised and stabilized for 40 minutes, adding the first initiator solution and the second mixed monomer into the reaction solution at the flow rates of 0.32mL/min and 1.26mL/min respectively.
(3) And dissolving 8.00g of azobisisobutyronitrile into 60g of isopropanol to obtain a second initiator solution, after the first initiator solution and the second mixed monomer are added, reacting for 2 hours, adding the second initiator solution into the reaction liquid at the flow rate of 12mL/min, and terminating the reaction after 40 minutes to obtain the dispersing agent.
Example 2
(1) Mixing 48.84g of n-butyl acrylate, 16.52g of methacrylic acid and 21.46g of methyl styrene to obtain a first mixed monomer, adding the first mixed monomer and 320g of isopropanol serving as a solvent into a reaction container with condensation reflux, introducing nitrogen, continuously stirring, and heating to 80 ℃;
(2) dissolving 20.00g of azobisisoheptonitrile in 100g of butanone to obtain a first initiator solution, stirring and mixing 154.67g of n-butyl acrylate, 52.30g of methacrylic acid and 80.59g of methyl styrene to obtain a second mixed monomer, and after the temperature in the step (1) is raised and stabilized for 40 minutes, adding the first initiator solution and the second mixed monomer into the reaction liquid at the flow rates of 0.41mL/min and 0.98mL/min respectively.
(3) 6g of azobisisobutyronitrile is dissolved in 45g of isopropanol to obtain a second initiator solution, after the first initiator solution and the second mixed monomer are added, the reaction is finished for 2 hours, and then the second initiator solution is added into the reaction solution at the flow rate of 8mL/min to react for 30 minutes, so that the dispersant is obtained.
Example 3
(1) Mixing 37.75g of vinyl pyrrolidone, 14.21g of ethylene glycol dimethacrylate and 21.46g of phenyl methacrylate to obtain a first mixed monomer, adding the first mixed monomer, 180g of butanone and 180g of isopropanol into a reaction vessel with condensation reflux, introducing nitrogen and continuously stirring, and heating to 80 ℃;
(2) dissolving 22.00g of azodicyano valeric acid in 140g of water to obtain a first initiator solution, stirring and mixing 160.91g of vinyl pyrrolidone, 60.59g of ethylene glycol dimethacrylate and 121.58g of phenyl methacrylate to obtain a second mixed monomer, and after the temperature in the step (1) is raised and stabilized for 35 minutes, adding the first initiator solution and the second mixed monomer into the reaction liquid at the flow rates of 0.35mL/min and 2.06mL/min respectively.
(3) And 4g of azodicyano valeric acid is dissolved in 40g of water to obtain a second initiator solution, after the first initiator solution and the second mixed monomer are added, the reaction is carried out for 1.5 hours, the second initiator solution is added into the reaction liquid at the flow rate of 9mL/min, and the reaction is terminated after 40 minutes, so that the dispersing agent is obtained.
Example 4
(1) Mixing 52.99g of ethoxy triethylene glycol methacrylate, 25.58g of allyl alcohol polyoxyethylene ether and 28.29g of p-methylstyrene to obtain a first mixed monomer, adding the first mixed monomer, 250g of solvent ethyl acetate and 100g of cyclohexanone into a reaction vessel with condensation reflux, introducing nitrogen and continuously stirring, and heating to 83 ℃;
(2) dissolving 24.00g of azobisisobutyronitrile into 100g of methanol to obtain a first initiator solution, stirring and mixing 129.74g of ethoxy triethylene glycol methacrylate, 62.63g of allyl alcohol polyoxyethylene ether and 113.15g of p-methylstyrene to obtain a second mixed monomer, and after the temperature in the step (1) is raised and stabilized for 45 minutes, adding the first initiator solution and the second mixed monomer into the reaction feed liquid at the flow rates of 0.56mL/min and 1.73mL/min respectively.
(3) 6.00g of azobisisobutyronitrile is dissolved in 50g of methanol to obtain a second initiator solution, and after the first initiator solution and the second mixed monomer are added and react for 2 hours, the second initiator solution is added into the reaction solution at the flow rate of 10mL/min to react for 60 minutes, so that the dispersant is obtained.
Example 5
The dispersant prepared in example 1 is used to prepare organic pigment color paste, and the steps are as follows:
stirring and mixing 70g of dispersing agent, 82g of C.I. pigment yellow 185 and 268g of deionized water to obtain pre-dispersion liquid;
and (3) grinding the pre-dispersion liquid in a grinding machine for 60min, and filtering to remove particles and colloid to obtain the stable organic pigment color paste.
Example 6
The dispersant prepared in example 2 is used for preparing organic pigment color paste, and the steps are as follows:
stirring and mixing 75g of dispersing agent, 80g of C.I. pigment orange 24 and 265g of deionized water to obtain pre-dispersion liquid;
and (3) grinding the pre-dispersion liquid in a grinding machine for 65min, and filtering to remove particles and colloid to obtain the stable organic pigment color paste.
Example 7
The dispersant prepared in example 3 is used to prepare organic pigment color paste, and the steps are as follows:
stirring and mixing 80g of dispersing agent, 85g of C.I. pigment red 9 and 275g of deionized water to obtain pre-dispersion liquid;
and (3) grinding the pre-dispersion liquid in a grinding machine for 55min, and filtering to remove particles and colloid to obtain the stable organic pigment color paste.
Example 8
The dispersant prepared in example 4 is used to prepare organic pigment color paste, and the steps are as follows:
stirring and mixing 70g of dispersing agent, 80g of C.I. pigment violet 3 and 270g of deionized water to obtain pre-dispersion liquid;
and (3) grinding the pre-dispersion liquid in a grinding machine for 60min, and filtering to remove particles and colloid to obtain the stable organic pigment color paste.
Comparative example 1
Other conditions were the same as in example 5 except that the dispersant was replaced with a commercially available acrylic dispersant, model DH-6530S.
And (3) performance testing:
(1) and (3) testing molecular weight: the dispersant prepared in examples 1 to 4 was subjected to a molecular weight test using Shimadzu gel permeation chromatograph LC-20 AD;
(2) and (3) viscosity testing: the organic pigment color paste prepared in the examples 5 to 8 is subjected to viscosity test by adopting a Brookfield (Wells cone and plate viscometer);
(3) and (3) particle size testing: the organic pigment color paste prepared in examples 5 to 8 was subjected to particle size testing using a Malvern Nano S90 nanometer particle size analyzer.
(4) And (3) stability testing: the organic pigment color paste prepared in the examples 5 to 8 and the comparative example 1 is aged for 10 days under the following aging conditions: and standing at 60 ℃ for 14 days, wherein the change rate of the particle size is within 10 percent, or the viscosity change is less than 5 percent, the color paste is qualified, otherwise, the color paste is unqualified.
The test results are shown in tables 1-2.
Table 1: examples 1-4 measurement of molecular weight of dispersant
The ratio of the weight average molecular weight to the number average molecular weight is called polydispersity and is used to measure the dispersion distribution of the molecular weight, the ratio is close to 1, which indicates that the more concentrated the molecular weight distribution, and the empty space provided by the dispersantThe steric hindrance tends to be consistent, and the dispersion effect is better. As can be seen from Table 1, the dispersants prepared in examples 1 to 4 have number average molecular weights of 10000 to 30000, weight average molecular weights of 10000 to 15000, Mw/MnThe value is about 1.5, which shows that the steric hindrance tends to be consistent and the dispersion effect is better.
TABLE 2 Performance test results of organic pigment pastes prepared in examples 5 to 8 and comparative example 1
| Test items | Example 5 | Example 6 | Example 7 | Example 8 | Comparative example 1 |
| Particle size D50 before aging (nm) | 97 | 98 | 95 | 102 | 312 |
| Particle size (nm) of aged D50 | 102 | 100 | 99 | 102 | 367 |
| Viscosity before aging (cp) | 24.3 | 13.6 | 15.2 | 9.8 | 50.3 |
| Viscosity after aging (cp) | 24.2 | 13.8 | 15.3 | 9.9 | 62.8 |
As can be seen from Table 2, under the condition that the grinding time is 55-65 min, the average particle size of the color paste obtained in the examples 5-8 is only about 100nm, while the particle size of the color paste prepared in the comparative example 1 is 312nm, which shows that the dispersant provided by the invention can obviously improve the grinding efficiency and reduce the grinding time required by the particle size to meet the requirement; in addition, according to the particle size and viscosity change data of the color paste before and after aging, the particle size and viscosity of the color paste provided by the invention are basically not changed before and after aging, while the particle size of the color paste prepared by the comparative example 1 is obviously increased, and the viscosity change is larger. The color paste provided by the invention has good stability.
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 three-component acrylate dispersant is characterized by being prepared from the following components in parts by mass: 5-30% of lipophilic monomer, 5-50% of hydrophilic monomer, 5-20% of monomer containing aromatic ring or heterocycle, 1-10% of initiator and 30-60% of solvent; at least one of the hydrophilic monomer and the lipophilic monomer is an acrylate monomer; the number average molecular weight of the three-component acrylate dispersing agent is 10000-30000, and the weight average molecular weight is 10000-30000.
2. The three-component acrylate dispersant according to claim 1, characterized in that said lipophilic monomer comprises one or more of methyl dicyclopentenyl acrylate, n-butyl acrylate, ethoxytriethylene glycol methacrylate, 2-phenoxyethyl methacrylate, vinyl pyrrolidone and phenoxyethyl acrylate;
the hydrophilic monomer comprises one or more of maleic anhydride, acrylic acid, methacrylic acid, allyl alcohol polyoxyethylene ether, ethylene glycol dimethacrylate and ethoxy triethylene glycol methacrylate;
the aromatic ring in the monomer containing the aromatic ring or the heterocycle is a benzene ring, and the heterocycle is an aromatic heterocycle.
3. The three-component acrylate dispersant according to claim 1 or 2, wherein the aromatic or heterocyclic ring containing monomer comprises one or more of benzyl methacrylate, tetrahydrofurfuryl methacrylate, methyl styrene, phenyl methacrylate, vinyl toluene and p-methyl styrene.
4. The three-component acrylate dispersant according to claim 1, characterized in that said initiator is an azo-based compound; the solvent comprises one or more of water, ketone solvent, alcohol solvent, ester solvent and benzene solvent.
5. The three-component acrylate dispersant according to claim 1, characterized in that the ratio of the weight average molecular weight to the number average molecular weight of the three-component acrylate dispersant is 1 to 2: 1.
6. A method for preparing the three-component acrylate dispersant of any one of claims 1 to 5, characterized by comprising the steps of:
mixing a lipophilic monomer, a hydrophilic monomer, a monomer containing aromatic rings or heterocyclic rings, an initiator and a solvent for polymerization reaction to obtain the three-component acrylate dispersing agent.
7. The method of claim 6, wherein the mixing to effect polymerization comprises:
mixing part of hydrophilic monomer, part of lipophilic monomer and part of monomer containing aromatic ring or heterocycle to obtain a first mixed monomer; mixing the residual hydrophilic monomer, the residual lipophilic monomer and the residual monomer containing aromatic ring or heterocycle to obtain a second mixed monomer;
mixing part of the initiator with the first part of the solvent to obtain a first initiator solution, and mixing the rest of the initiator with the second part of the solvent to obtain a second initiator solution;
mixing the first mixed monomer with the rest solvent, and carrying out a first polymerization reaction under the protection of inert gas to obtain a first polymerization reaction feed liquid; mixing the first initiator solution, the second mixed monomer and the first reaction feed liquid, and carrying out a second polymerization reaction to obtain a second reaction feed liquid; and adding the second initiator solution into the second reaction solution to terminate the reaction.
8. The method according to claim 7, wherein the first polymerization reaction and the second polymerization reaction are independently carried out at a temperature of 70 to 90 ℃, the time of the first polymerization reaction is 30 to 40min, and the time of the second polymerization reaction is 1 to 2 hours.
9. The organic pigment color paste is characterized by comprising the following components in percentage by mass: 10-40% of a dispersing agent, 15-40% of an organic pigment and 20-80% of a dispersing medium; the dispersant is the three-component acrylate dispersant of any one of claims 1 to 5 or the three-component acrylate dispersant prepared by the preparation method of any one of claims 6 to 8; the organic pigment is an organic pigment containing an aromatic ring or a heterocyclic ring.
10. The method for preparing the organic pigment paste according to claim 9, which is characterized by comprising the following steps:
mixing a dispersing agent, an organic pigment and a dispersing medium to obtain a pre-dispersion liquid;
and grinding the pre-dispersion liquid and filtering to obtain the organic pigment color paste.
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