CN116425993A - Preparation method of hyperbranched polycarboxylate dispersant - Google Patents
Preparation method of hyperbranched polycarboxylate dispersant Download PDFInfo
- Publication number
- CN116425993A CN116425993A CN202310489731.6A CN202310489731A CN116425993A CN 116425993 A CN116425993 A CN 116425993A CN 202310489731 A CN202310489731 A CN 202310489731A CN 116425993 A CN116425993 A CN 116425993A
- Authority
- CN
- China
- Prior art keywords
- compound
- reaction
- hyperbranched
- polyamino
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 49
- 229920005646 polycarboxylate Polymers 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- -1 amino carboxylic acid compound Chemical class 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 22
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 238000010438 heat treatment Methods 0.000 claims description 14
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 8
- 238000007865 diluting Methods 0.000 claims description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 238000004321 preservation Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims description 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 claims description 2
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 claims description 2
- OYRSKXCXEFLTEY-UHFFFAOYSA-N 1-[2-[2-[2-[2-(2,5-dioxopyrrol-1-yl)ethoxy]ethoxy]ethoxy]ethyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCOCCOCCOCCN1C(=O)C=CC1=O OYRSKXCXEFLTEY-UHFFFAOYSA-N 0.000 claims description 2
- FYBFGAFWCBMEDG-UHFFFAOYSA-N 1-[3,5-di(prop-2-enoyl)-1,3,5-triazinan-1-yl]prop-2-en-1-one Chemical compound C=CC(=O)N1CN(C(=O)C=C)CN(C(=O)C=C)C1 FYBFGAFWCBMEDG-UHFFFAOYSA-N 0.000 claims description 2
- YERHJBPPDGHCRJ-UHFFFAOYSA-N 1-[4-(1-oxoprop-2-enyl)-1-piperazinyl]-2-propen-1-one Chemical compound C=CC(=O)N1CCN(C(=O)C=C)CC1 YERHJBPPDGHCRJ-UHFFFAOYSA-N 0.000 claims description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- NFQAIWOMJQWGSS-UHFFFAOYSA-N 3-amino-3-methylbutanoic acid Chemical compound CC(C)(N)CC(O)=O NFQAIWOMJQWGSS-UHFFFAOYSA-N 0.000 claims description 2
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims description 2
- QCTBMLYLENLHLA-UHFFFAOYSA-N aminomethylbenzoic acid Chemical compound NCC1=CC=C(C(O)=O)C=C1 QCTBMLYLENLHLA-UHFFFAOYSA-N 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 2
- 229940102253 isopropanolamine Drugs 0.000 claims description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003002 pH adjusting agent Substances 0.000 claims description 2
- 229920002401 polyacrylamide Polymers 0.000 claims description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 1
- 239000002245 particle Substances 0.000 abstract description 10
- 239000002994 raw material Substances 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 229910000510 noble metal Inorganic materials 0.000 abstract description 5
- 238000000746 purification Methods 0.000 abstract description 5
- 238000000926 separation method Methods 0.000 abstract description 5
- 238000006845 Michael addition reaction Methods 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 4
- 238000010979 pH adjustment Methods 0.000 abstract description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000007788 liquid Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 17
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 14
- 239000000049 pigment Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 8
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 6
- 239000011324 bead Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 229910052726 zirconium Inorganic materials 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 125000002843 carboxylic acid group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 150000007942 carboxylates Chemical group 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004873 anchoring Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 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 2
- 239000000945 filler Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229920006150 hyperbranched polyester Polymers 0.000 description 2
- 229920000587 hyperbranched polymer Polymers 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229940023462 paste product Drugs 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000001038 titanium pigment Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/005—Hyperbranched macromolecules
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/91—Use of waste materials as fillers for mortars or concrete
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)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
The invention discloses a preparation method of hyperbranched polycarboxylate dispersant, which takes amino carboxylic acid compound or acrylic acid as a main raw material, and obtains hyperbranched polycarboxylic acid through one-step Michael addition reaction with poly-acrylamide and polyamino compound, and the target product is obtained after pH adjustment. The method adopts the easily available compound as the initial raw material, has simple operation, no need of separation and purification, mild reaction conditions, no emission, no noble metal participation, low cost, low requirement on equipment and easy industrialized production; the product structure is stable and controllable. The hyperbranched polycarboxylate prepared by the method can be used as a novel dispersing agent for color paste, and the obtained color paste has low viscosity and small and uniform size of toner particles.
Description
Technical Field
The invention belongs to the technical field of polymer high molecular materials and synthesis thereof and the field of color paste, and particularly relates to a preparation method of hyperbranched polycarboxylate and application of the hyperbranched polycarboxylate in the color paste.
Background
The aqueous dispersing agent is an indispensable component in the fields of printing ink, color paste and the like. Its main function is to improve pigment dispersibility, stability, tinting strength and gloss. With the increasing market demands and the increasing technical level, and the diversity of pigments and fillers, various dispersants of various colors have been developed. The high molecular dispersing agent is also called hyperdispersant, and has a long molecular chain, so that a plurality of adsorption points or a large adsorption surface can be formed on the surface of the dispersed particles, and meanwhile, the hydrophilic chain segment can provide more charge or steric hindrance, so that a more stable dispersed state is obtained. In addition, the hyperdispersant can also reduce the viscosity of a grinding system, improve the pigment/base ratio, shorten the grinding time and improve the production efficiency. Accordingly, hyperdispersants have become the most popular commercial dispersants in the market.
At present, the hyper-dispersant is mainly made of linear polymers and is mainly obtained by combining anchoring groups and solvated chains, wherein the anchoring groups and the solvated chains have adsorption effect on pigment and filler in various polymerization modes. The latest generation of hyperdispersant belongs to a block polymer, and the block dispersant prepared by a controllable polymerization technology can accurately design and regulate and control a molecular structure according to requirements, so that an excellent dispersing effect is shown. However, the synthesis of such dispersants is quite expensive, subject to a complex state of the art. Therefore, the hyperdispersant is widely applied to high-end fields such as ink-jet printing, high-end coating and the like. In addition, the linear hyperdispersant often has entanglement of molecular chains, and an ultralow-viscosity color paste system is difficult to obtain when the high-solid-content color paste is prepared. The hyperbranched polymer has good solubility and low viscosity because of no chain entanglement effect among molecules due to the unique spherical topological structure, and can obtain an ultra-low viscosity color paste system when being applied to pigment dispersion, thereby realizing the high-content low-viscosity effect pursued by industry. For example, CN201410314464.X adopts acid anhydride to react with hyperbranched polyester, and then reacts with a compound with a monoepoxy functional group at one end and a hydrophobic long carbon chain at the other end to prepare the hyperbranched polyester pigment dispersing agent, and the dispersing agent can enable paint or color paste to be ground to meet the fineness requirement in a short time. For example, CN201410718471.6 can be used for preparing the water-based hyperbranched dispersing agent containing hydroxyl, ethoxy and a hydrophobic carbon chain with 5-8 carbons, so that the stability of the color paste paint can be improved, and the color difference can be reduced. CN201810209767.3 discloses an amphiphilic hyperbranched polymer comprising a backbone structure containing amine groups and a monocyclic, polycyclic, fused or heterocyclic aryl group covalently bonded to the backbone structure that is non-covalently associated with the graphene structure, which dispersant can be used for aqueous dispersion of carbon materials containing graphene structures.
Although hyperbranched dispersants exhibit very excellent properties in the field of color pastes, the synthesis process of such polymers is relatively complex, and organic solvents are often used to prevent crosslinking of the system, and post-treatment is cumbersome. At the same time, the introduction of the organic solvent also has a negative effect on the environment. Based on the method, the amino carboxylic acid compound or the acrylic acid is used as a main raw material, hyperbranched polycarboxylic acid is obtained by one-step Michael addition reaction of the amino carboxylic acid compound or the acrylic acid, and the target product is obtained after pH adjustment. The method adopts the easily available compound as the initial raw material, has simple operation, no need of separation and purification, mild reaction conditions, no emission, no noble metal participation, low cost, low requirement on equipment and easy industrialized production; the product structure is stable and controllable. The hyperbranched polycarboxylate prepared by the method can be used as a novel dispersing agent for color paste, and the obtained color paste has low viscosity and small and uniform size of toner particles.
Disclosure of Invention
The invention aims at solving the problems existing in the prior art and provides a preparation method of a hyperbranched polycarboxylate dispersant.
The aim of the invention can be achieved by the following scheme:
in a first aspect, the present invention provides a method for preparing a hyperbranched polycarboxylate dispersant, the method comprising the steps of:
s1, mixing and stirring a poly-acrylamide compound, a catalyst and a solvent, and heating;
s2, diluting a polyamino compound and an aminocarboxylic acid compound, then adding the diluted polyamino compound and the aminocarboxylic acid compound into the solution obtained in the step S1, heating for reaction, adding acrylic acid, and carrying out heat preservation for reaction;
or diluting the polyamino compound, adding the diluted polyamino compound into the solution obtained in the step S1, heating for reaction, adding acrylic acid, and carrying out heat preservation for reaction;
or diluting polyamino compounds and aminocarboxylic acids, then adding the diluted polyamino compounds and aminocarboxylic acids into the solution obtained in the step S1, and heating for reaction;
and S3, adding a pH regulator to regulate the pH of the system, and obtaining the hyperbranched polycarboxylate dispersant.
As an embodiment of the present invention, the polyacrylamide compound in step S1 includes one or more of N, N '-methylenebisacrylamide, N-bisacrylhexamethylenediamine, N' -vinylbisacrylamide, 1,3, 5-triacryloylhexahydro-1, 3, 5-triazine, 1, 4-bisacrylylpiperazine, N '- (1, 4-phenylene) bismaleimide, N' - (oxydimethylene) bismaleimide, 1, 11-bismaleimido-3, 6, 9-trioxaundecane, bisacrylamide polyether.
As an embodiment of the present invention, in step S1, the solvent includes one or more of water, N-dimethylformamide, dimethylacetamide, tetrahydrofuran, methanol, ethanol, butanol, pentanol, hexanol, ethylene glycol methyl ether, propylene glycol methyl ether, glycerol, diethylene glycol, polyethylene glycol.
As an embodiment of the present invention, the catalyst in step S1 includes one or more of sodium p-toluenesulfonate, tetrabutylammonium bromide, copper acetate, aluminum trichloride, ferric trichloride, titanium tetrachloride, boric acid, bismuth nitrate.
In step S1, as an embodiment of the present invention, the heating temperature is 30 ℃ to 75 ℃, and when the solution heating temperature is reached, the next step is performed.
In step S2, at least an aminocarboxylic acid compound or acrylic acid is included in the reaction substrate combination as an embodiment of the present invention.
As an embodiment of the present invention, in step S2, the polyamino compound includes one or more of ethylenediamine, propylenediamine, pentylene diamine, hexylenediamine, decylenediamine, hydroxyethylethylenediamine, N-aminoethylpiperazine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, N- (2-hydroxypropyl) ethylenediamine.
As an embodiment of the present invention, in step S2, the aminocarboxylic acids include one or more of twenty amino acids, β -aminopropionic acid, γ -aminobutyric acid, 4- (aminomethyl) benzoic acid, 3-amino-3-methylbutanoic acid.
The molar ratio of the total active hydrogen to the total olefin bond groups is 1.6-1.1: 1. the total active hydrogen is the hydrogen on the amino group that can undergo a Michael addition reaction with an olefin. The total active hydrogen is the sum of the amino hydrogen on the polyamino compound and the amino hydrogen on the aminocarboxylic acid compound; the total olefinic bond group is the sum of the double bonds on the poly-acrylamide compound, the double bonds on acrylic acid.
As one embodiment of the invention, in the step S2, the heating reaction is carried out at a temperature of 30-150 ℃ for 2-180 hours.
As one embodiment of the invention, in the step S2, the temperature of the heat preservation reaction is 30-150 ℃ and the time is 1-180 h.
In step S2, a polyamino compound is added, and a monoamino compound is also added. The monoamino compound is selectively added or not added, and the hydrophilic or hydrophobic monoamino compound can be added according to specific requirements, so that the performance diversity of the product is improved.
As an embodiment of the present invention, in step S2, the monoamino compound includes one or more of ethanolamine, propanolamine, isopropanolamine, butanolamine, isobutanolamine, diglycolamine, pentanolamine, hexanolamine, polyetheramine, oleylamine, octylamine, laurylamine, octadecylamine, benzylamine, n-hexylamine, butylamine. When the monoamino compound is added, the total active hydrogen is the sum of the amino hydrogen on the polyamino compound, the amino hydrogen on the aminocarboxylic acid compound and the amino hydrogen on the monoamino compound.
As an embodiment of the present invention, in step S3, the pH adjuster includes one or more of triethylamine, sodium hydroxide, potassium hydroxide, ethanolamine, ammonia water, urea, triethanolamine, and diethanolamine.
In one embodiment of the present invention, in step S3, the pH is controlled to be between 8.0 and 12.0. Adjusting the pH is to convert carboxylic acid groups on the molecule to carboxylate groups. Too high a pH results in reduced product stability and too low a pH results in no dispersing effect.
The synthesis method adopts the easily available commercial compounds as the initial raw materials, and the final product is obtained through one-pot reaction, so that the whole process is simple to operate, separation and purification are not needed, the reaction condition is mild, noble metal or catalyst participation is not needed, the cost is low, the equipment requirement is low, the whole process is green and pollution-free, and the popularization is easy; the product has regular molecular structure, controllable molecular weight and narrow molecular weight distribution.
In a second aspect, the invention relates to an application of the hyperbranched polycarboxylate as an aqueous dispersant in the color paste field, wherein the hyperbranched polycarboxylate is added into an aqueous solution containing pigment, and the color paste with low viscosity, small and uniform size of toner particles can be obtained after dispersion grinding, and the addition amount of the hyperbranched polycarboxylate dispersant is 0.5-10%. The pigment is one pigment of iron oxide red, iron oxide yellow, iron oxide black, phthalocyanine blue, titanium pigment and carbon black. The pigment content is 1% -60%.
Compared with the prior reported synthesis technology of the linear carboxylate dispersant or the hyperbranched dispersant, the invention has the following beneficial effects:
1) The polycarboxylate dispersant provided by the invention has a hyperbranched structure, no molecular entanglement exists among molecules, and the polycarboxylate dispersant has the advantages of small dosage, low viscosity, multiple functional groups and strong solubility;
2) The synthesis technology provided by the invention adopts an easily available commercial raw material amino carboxylic acid compound or acrylic acid as a main raw material, and the main raw material and the multi-acrylamide compound are subjected to Michael addition reaction to obtain hyperbranched polycarboxylic acid in one step, and the target product is obtained after pH adjustment. The method adopts the easily available compound as the initial raw material, has simple operation, no need of separation and purification, mild reaction conditions, no emission, no noble metal participation, low cost, low requirement on equipment and easy industrialized production; the product structure is stable and controllable;
3) The hyperbranched polycarboxylate dispersant is used in a water-based color paste system, has more anchoring groups, large molecular weight, longer chain length and larger steric hindrance, can greatly reduce mutual collision of pigment particles, prevent flocculation of solid particles, and overcomes the defects of weak adsorption, easy stripping and the like of the traditional dispersant on the surfaces of the pigment particles, so that an ultra-low viscosity high-solid-content color paste product can be obtained.
Drawings
Other features, objects and advantages of the present invention will become more apparent upon reading of the detailed description of non-limiting embodiments, given with reference to the accompanying drawings in which:
FIG. 1 is a schematic structural diagram of a hyperbranched polycarboxylate of the present invention;
FIG. 2 is a nuclear magnetic resonance spectrum of dispersant 3 of the present invention;
FIG. 3 is a schematic molecular structure of the dispersant 3 of the present invention.
Detailed Description
The process, conditions, reagents, experimental methods, etc. for carrying out the present invention will be described in further detail with reference to the following specific examples, which are generally known and commonly known in the art, except as specifically mentioned below. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The invention provides a preparation method of hyperbranched polycarboxylate dispersant, which comprises the steps of diluting a mixture of one or more polyamino compounds, one or more monoprimary amine compounds and one or more aminocarboxylic acids in a certain proportion at a certain temperature, adding the mixture into a mixed solution which is uniformly mixed in advance and contains one or more bisacrylamide compounds, reacting for a certain period of time at a certain temperature, adding a certain proportion of acrylic acid in the presence or absence of the mixture, continuing reacting for a certain period of time at a certain temperature, cooling to room temperature after the reaction is finished, and adding a certain amount of pH regulator to obtain a target product. The method adopts the easily available compound as the initial raw material, has simple operation, no need of separation and purification, mild reaction conditions, no emission, no noble metal participation, low cost, low requirement on equipment and easy industrialized production; the product structure is stable and controllable. The synthesis steps comprise the following two steps:
s1, adding a solvent and one or more bisacrylamide compounds into a reaction kettle, stirring and mixing uniformly, starting a heating mode, and performing a second step after the temperature reaches a set value;
s2, diluting a mixture of one or more polyamino compounds, one or more monoprimary amine compounds and one or more aminocarboxylic acids in a certain proportion by a solvent, adding the diluted mixture into a reaction system of the previous step, and reacting for a certain time at a certain temperature;
s3, adding a certain proportion of acrylic acid or not, stirring at a given temperature for reacting for a period of time, stopping the reaction, and cooling to room temperature;
s4, adding a pH regulator into the system, and regulating the pH of the system to a certain value to obtain a target product, wherein the target product is shown in figure 1.
The technique of the present invention will be further illustrated by the following examples.
Comparative example 1
Into a three-necked flask, 11.9g of methylene bisacrylamide and 50mg of sodium p-toluenesulfonate were added, 25mL of water was added, the mixture was stirred uniformly and transferred to an oil bath at 60℃until the temperature of the reaction solution was raised to 60℃and 10-g N-aminoethylpiperazine was diluted with 10mL of water and added to the flask. After 2 days of reaction, the mixture was cooled to room temperature to obtain a dispersion 1. The property is light yellow viscous liquid. Since no carboxylic acid monomer is added, dispersant 1 is a hyperbranched polyamide-amine structure, with no carboxylic acid groups.
Comparative example 2
Into a three-necked flask, 11.9g of methylene bisacrylamide and 50mg of sodium p-toluenesulfonate were added, 25mL of water was added, the mixture was stirred uniformly and transferred to an oil bath at 60℃until the temperature of the reaction solution was raised to 60℃and 10-g N-aminoethylpiperazine was diluted with 15mL of water and added to the flask. After 2 days of reaction, 2.4g of acrylic acid was added to the system. And after the reaction is continued for 2 days, cooling to room temperature to obtain the dispersing agent 2. The property is light yellow viscous liquid. After acrylic acid post-modification, the obtained dispersant 2 is of a hyperbranched polycarboxylic acid structure, and the carboxylic acid group is not converted into carboxylate.
Example 1
Into a three-necked flask, 11.9g of methylene bisacrylamide and 50mg of sodium p-toluenesulfonate were added, 25mL of water was added, the mixture was stirred uniformly and transferred to an oil bath at 60℃until the temperature of the reaction solution was raised to 60℃and 10-g N-aminoethylpiperazine was diluted with 15mL of water and added to the flask. After 2 days of reaction, 2.4g of acrylic acid (molar ratio of total active hydrogen to total olefinic groups 1.2:1) was added to the system. After the reaction was continued for 2 days, it was cooled to room temperature. And adding triethylamine to adjust the pH of the system to 10 to obtain the dispersion 3. The structure is shown in figure 3, and the property is light yellow viscous liquid. The nuclear magnetic carbon spectrum (figure 2) shows carbon atom signals '9 and 10' belonging to branching units, which indicate that the product is in a hyperbranched structure, and the branching degree is 0.40. In comparison to the comparative examples, not only is carboxylic acid added for the functional modification, but also the carboxylic acid groups are further converted into carboxylate groups.
Example 2
14.8g of methylene bisacrylamide and 50mg of sodium p-toluenesulfonate were put into a three-necked flask, 40mL of water was added, the mixture was stirred uniformly and transferred to an oil bath at 60℃until the temperature of the reaction solution was raised to 60℃and 8.7. 8.7g N-aminoethylpiperazine and 4g of diglycolamine were diluted with 20mL of water and added to the flask. After 2 days of reaction, 4.4g of acrylic acid were added to the system, wherein the molar ratio of total active hydrogen to total olefinic groups was 1.1:1. After the reaction was continued for 2 days, it was cooled to room temperature. The system was then adjusted to pH 10 by the addition of triethylamine to give dispersion 4. The property is light yellow viscous liquid.
Example 3
14.8g of methylene bisacrylamide and 50mg of sodium p-toluenesulfonate were put into a three-necked flask, 40mL of water was added, the mixture was stirred uniformly and transferred to an oil bath at 60℃until the temperature of the reaction solution was raised to 60℃and 8.7. 8.7g N-aminoethylpiperazine and 4g of diglycolamine were diluted with 20mL of water and added to the flask. The reaction solution was heated to 150℃and after 2 hours of reaction 4.4g of acrylic acid were added to the system, wherein the molar ratio of total active hydrogen to total olefinic groups was 1.1:1. The reaction was continued for 1 hour and then cooled to room temperature. And adding triethylamine to adjust the pH of the system to 10 to obtain the dispersion 5. The property is light yellow viscous liquid.
Example 4
In this example, the solvent was ethylene glycol and the product was designated dispersant 6 under the same conditions as in example 2. The character is brown sugar viscous liquid.
Example 5
9.2g of methylene bisacrylamide and 50mg of sodium paratoluenesulfonate are added into a three-necked flask, 20mL of water is added, the mixture is stirred uniformly and then transferred into an oil bath pot at 60 ℃, when the temperature of reaction liquid is raised to 60 ℃, 4.1g N-aminoethylpiperazine, 2.4g of glycine and 1.7g of diglycolamine are diluted by 6mL of water, and the mixture is added into the flask, wherein the molar ratio of total active hydrogen to total olefin bond groups is 1.6:1. After 2 days of reaction, the mixture was cooled to room temperature. The pH of the system was then adjusted to 10 by the addition of triethylamine to give dispersion 7. The property is light yellow viscous liquid.
Example 6
In this example, 13g of methylene bisacrylamide was added, and the result was dispersant 8 under the same conditions as in example 5. The property is light yellow viscous liquid.
Example 7
Into a three-necked flask, 11.9g of methylene bisacrylamide and 50mg of sodium p-toluenesulfonate were charged, 25mL of water was added, and after stirring uniformly, the mixture was transferred to an oil bath at 60℃and when the temperature of the reaction liquid rose to 60℃4.1. 4.1g N-aminoethylpiperazine and 1g of glycine were diluted with 15mL of water, and added to the flask. After 2 days of reaction, 1.4g of acrylic acid was added to the system, wherein the molar ratio of total active hydrogen to total olefinic groups was 1.4:1. After the reaction was continued for 2 days, it was cooled to room temperature. The pH of the system was then adjusted to 10 by the addition of triethylamine to obtain dispersion 9. The property is light yellow viscous liquid.
The application effect of the hyperbranched polycarboxylate dispersant in the color paste is described below by specific examples.
4 parts of hyperbranched dispersant 1, 20 parts of iron oxide red, 76 parts of water and 200 parts of zirconium beads are added into a mixer to be dispersed for 60 minutes at a rotating speed of 3000r/min, so as to obtain the comparative color paste 1.
Adding 4 parts of hyperbranched dispersant 2, 20 parts of iron oxide red, 76 parts of water and 200 parts of zirconium beads into a mixer, and dispersing for 60 minutes at a rotating speed of 3000r/min to obtain comparative color paste 2
The same operations are carried out on the dispersants 3 to 9 respectively to obtain color pastes 3 to 9.
2 parts of hyperbranched dispersant 3, 20 parts of iron oxide red, 78 parts of water and 200 parts of zirconium beads are added into a mixer to be dispersed for 60 minutes at a rotating speed of 3000r/min, so as to obtain color paste 10.
8 parts of hyperbranched dispersant 3, 20 parts of iron oxide red, 72 parts of water and 200 parts of zirconium beads are added into a mixer to be dispersed for 60 minutes at a rotating speed of 3000r/min to obtain color paste 11.
6 parts of hyperbranched dispersant 3, 40 parts of iron oxide red, 54 parts of water and 200 parts of zirconium beads are added into a mixer to be dispersed for 60 minutes at a rotating speed of 3000r/min to obtain color paste 12.
4 parts of hyperbranched dispersant 3, 20 parts of phthalocyanine blue, 76 parts of water and 200 parts of zirconium beads are added into a mixer to be dispersed for 60 minutes at a rotating speed of 3000r/min to obtain color paste 13.
All the color pastes were tested for viscosity and particle size, and the results are shown in the following table:
table 1 shows the viscosity and particle diameter (D95) data of the above color paste
| Composition of the composition | Color paste character | Viscosity (cP) | D95(μm) |
| Contrast color paste 1 | Paste form | — | 2.5 |
| Contrast color paste 2 | Paste form | — | 2.8 |
| |
Liquid state | 4.5 | 0.34 |
| Color paste 4 | Liquid state | 3.6 | 0.26 |
| Color paste 5 | Liquid state | 4.1 | 0.27 |
| Color paste 6 | Liquid state | 3.7 | 0.30 |
| |
Liquid state | 3.8 | 0.29 |
| |
Liquid state | 3.4 | 0.28 |
| Color paste 9 | Liquid state | 3.6 | 0.27 |
| |
Liquid state | 4.2 | 0.27 |
| Color paste 11 | Liquid state | 4.7 | 0.31 |
| Color paste 12 | Liquid state | 4.8 | 0.33 |
| Color paste 13 | Liquid state | 4.6 | 0.31 |
As can be seen from table 1, the hyperbranched polycarboxylate dispersant provided by the examples of the present application can disperse high-concentration pigment, can obtain color paste with low viscosity and small particle size, and can completely obtain the effect of high content and low viscosity, compared with the dispersant without carboxylic acid group and without pH adjustment.
The foregoing embodiments may be partially modified in numerous ways by those skilled in the art without departing from the principles and spirit of the invention, the scope of which is defined in the claims and not by the foregoing embodiments, and all such implementations are within the scope of the invention.
Claims (10)
1. A method for preparing a hyperbranched polycarboxylate dispersant, characterized in that the method comprises the following steps:
s1, mixing and stirring a poly-acrylamide compound, a catalyst and a solvent, and heating;
s2, diluting a polyamino compound and an aminocarboxylic acid compound, then adding the diluted polyamino compound and the aminocarboxylic acid compound into the solution obtained in the step S1, heating for reaction, adding acrylic acid, and carrying out heat preservation for reaction;
or diluting the polyamino compound, adding the diluted polyamino compound into the solution obtained in the step S1, heating for reaction, adding acrylic acid, and carrying out heat preservation for reaction;
or diluting polyamino compounds and aminocarboxylic acid compounds, then adding the diluted polyamino compounds and aminocarboxylic acid compounds into the solution obtained in the step S1, and heating for reaction;
and S3, adding a pH regulator to regulate the pH of the system, and obtaining the hyperbranched polycarboxylate dispersant.
2. The method according to claim 1, wherein in the step S1, the polyacrylamide compound includes one or more of N, N '-methylenebisacrylamide, N-bisacrylhexamethylenediamine, N' -vinylbisacrylamide, 1,3, 5-triacryloylhexahydro-1, 3, 5-triazine, 1, 4-bisacrylylpiperazine, N '- (1, 4-phenylene) bismaleimide, N' - (oxydimethylene) bismaleimide, 1, 11-bismaleimido-3, 6, 9-trioxaundecane, bisacrylamide polyether.
3. The method of claim 1, wherein in step S1, the heating is performed at a temperature of 30 ℃ to 75 ℃.
4. The method according to claim 1, wherein in the step S2, the polyamino compound includes one or more of ethylenediamine, propylenediamine, pentylene diamine, hexamethylenediamine, decylenediamine, hydroxyethylethylenediamine, N-aminoethylpiperazine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, and N- (2-hydroxypropyl) ethylenediamine.
5. The method according to claim 1, wherein in step S2, the aminocarboxylic acid compound comprises one or more of twenty amino acids, β -aminopropionic acid, γ -aminobutyric acid, 4- (aminomethyl) benzoic acid, 3-amino-3-methylbutanoic acid.
6. The process according to claim 1, wherein the molar ratio of total active hydrogen to total olefinic bond groups is from 1.6 to 1.1:1, a step of; the total active hydrogen is the sum of the amino hydrogen on the polyamino compound and the amino hydrogen on the aminocarboxylic acid compound; the total olefinic bond group is the sum of the double bonds on the poly-acrylamide compound, the double bonds on acrylic acid.
7. The preparation method according to claim 1, wherein in the step S2, the heating reaction is performed at a temperature of 30 ℃ to 150 ℃ for a time of 2h to 180h; the temperature of the heat preservation reaction is 30-150 ℃ and the time is 1-180 h.
8. The method according to claim 1, wherein in step S2, a monoamino compound is further added when the polyamino compound is added; the monoamine compound comprises one or more of ethanolamine, propanolamine, isopropanolamine, butanolamine, isobutyrolamine, diglycolamine, valerolamine, caprolamine, polyether amine, oleylamine, octylamine, laurylamine, octadecylamine, benzylamine, n-hexylamine and butylamine.
9. The preparation method according to claim 1, wherein in the step S3, the pH adjuster comprises one or more of triethylamine, sodium hydroxide, potassium hydroxide, ethanolamine, ammonia water, urea, triethanolamine, diethanolamine; the pH is controlled between 8.0 and 12.0.
10. Use of the hyperbranched polycarboxylate prepared by the preparation method according to claim 1 as an aqueous dispersant in the field of color pastes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310489731.6A CN116425993A (en) | 2023-04-28 | 2023-04-28 | Preparation method of hyperbranched polycarboxylate dispersant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310489731.6A CN116425993A (en) | 2023-04-28 | 2023-04-28 | Preparation method of hyperbranched polycarboxylate dispersant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116425993A true CN116425993A (en) | 2023-07-14 |
Family
ID=87083288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310489731.6A Pending CN116425993A (en) | 2023-04-28 | 2023-04-28 | Preparation method of hyperbranched polycarboxylate dispersant |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116425993A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116554756A (en) * | 2023-04-28 | 2023-08-08 | 上海交通大学 | High-performance special coating and preparation method thereof |
-
2023
- 2023-04-28 CN CN202310489731.6A patent/CN116425993A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116554756A (en) * | 2023-04-28 | 2023-08-08 | 上海交通大学 | High-performance special coating and preparation method thereof |
| CN116554756B (en) * | 2023-04-28 | 2024-03-22 | 上海交通大学 | High-performance special coating and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI293963B (en) | Epoxide adducts and their salts as dispersants | |
| CN108034305B (en) | Ferric oxide pigment color paste and preparation method thereof | |
| WO2015021933A1 (en) | Hyperbranched polyester resin pigment dispersant, preparation method for same, color paste thereof, and application of the color paste | |
| CN116425993A (en) | Preparation method of hyperbranched polycarboxylate dispersant | |
| JP2013512990A (en) | Production and use of high molecular weight dispersant compositions | |
| CN108727952A (en) | A kind of self-emulsification aqueous alkyd resin and self-emulsification aqueous alkyd paint and preparation method | |
| JP2015533887A (en) | Hyperbranched phosphate ester | |
| CN109020859B (en) | Water-soluble cationic polyaspartic acid ester and preparation method and application thereof | |
| CN110845913A (en) | Reactive water-based color paste and preparation method thereof | |
| CN107075106B (en) | Comb type polyurethane dispersant | |
| CN101380555B (en) | Dispersant for salicylic acid derivatives pigments and preparation method and use thereof | |
| JP6009725B2 (en) | Pigment dispersion | |
| CN111040181A (en) | Polyacrylate dispersant and preparation method thereof | |
| TWI548673B (en) | Polymer and dispersion | |
| CN116554756B (en) | High-performance special coating and preparation method thereof | |
| CN106543432A (en) | A kind of water-soluble polymer and its preparation method and application | |
| CN110540639B (en) | Parallel-connection type high-molecular water-based organic pigment dispersant, and preparation and application thereof | |
| CN108300181B (en) | Stable powder slurry and preparation method and application thereof | |
| JP4396210B2 (en) | Pigment dispersant, pigment composition, and pigment dispersion | |
| JPH06206992A (en) | Surfactant based on alkoxylated fatty acid amine | |
| CN109749073B (en) | Water-phase easily-dispersible metal ion-loaded hyperbranched polymer and preparation method thereof | |
| CN101205418B (en) | Polyether primary amine derivative disperser for paint, preparation and use thereof | |
| CN114716685B (en) | Polycarboxylic acid dispersant, preparation method thereof, polycarboxylic acid dispersant and application | |
| CN109777221B (en) | Water-based paint containing hyperbranched polymer loaded with metal ions and preparation method thereof | |
| CN115073969B (en) | Water-based environment-friendly nano modified ink and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |