CN109679398A - A kind of polyurethane based water-based coating hyper-dispersant and preparation method thereof - Google Patents
A kind of polyurethane based water-based coating hyper-dispersant and preparation method thereof Download PDFInfo
- Publication number
- CN109679398A CN109679398A CN201811539902.7A CN201811539902A CN109679398A CN 109679398 A CN109679398 A CN 109679398A CN 201811539902 A CN201811539902 A CN 201811539902A CN 109679398 A CN109679398 A CN 109679398A
- Authority
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- China
- Prior art keywords
- hyper
- dispersant
- compound
- polyurethane
- water
- 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.)
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Links
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 239000004814 polyurethane Substances 0.000 title claims abstract description 32
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 32
- 238000000576 coating method Methods 0.000 title claims abstract description 30
- 239000011248 coating agent Substances 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 64
- 239000002904 solvent Substances 0.000 claims abstract description 23
- -1 sulfamic acid compound Chemical class 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 239000002994 raw material Substances 0.000 claims abstract description 17
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 15
- 150000001298 alcohols Chemical class 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 63
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 48
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 45
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 claims description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 30
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 20
- 229940113088 dimethylacetamide Drugs 0.000 claims description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 11
- LZKGFGLOQNSMBS-UHFFFAOYSA-N 4,5,6-trichlorotriazine Chemical compound ClC1=NN=NC(Cl)=C1Cl LZKGFGLOQNSMBS-UHFFFAOYSA-N 0.000 claims description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 8
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- 229940031098 ethanolamine Drugs 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- WQPMYSHJKXVTME-UHFFFAOYSA-N 3-hydroxypropane-1-sulfonic acid Chemical compound OCCCS(O)(=O)=O WQPMYSHJKXVTME-UHFFFAOYSA-N 0.000 claims description 5
- SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Aminopropanesulfonate Chemical compound NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 4
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical group NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 claims description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
- 229960004063 propylene glycol Drugs 0.000 claims description 4
- 229940043375 1,5-pentanediol Drugs 0.000 claims description 3
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 claims description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 3
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical compound ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 claims 1
- 241000218195 Lauraceae Species 0.000 claims 1
- 235000017858 Laurus nobilis Nutrition 0.000 claims 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 claims 1
- 238000005576 amination reaction Methods 0.000 claims 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 abstract description 7
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003973 paint Substances 0.000 abstract description 4
- 239000002912 waste gas Substances 0.000 abstract description 3
- 239000002351 wastewater Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 239000003814 drug Substances 0.000 description 16
- 229940079593 drug Drugs 0.000 description 16
- 239000000047 product Substances 0.000 description 13
- 239000000049 pigment Substances 0.000 description 12
- 238000011017 operating method Methods 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 239000012752 auxiliary agent Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920000570 polyether Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- 239000004721 Polyphenylene oxide Chemical class 0.000 description 3
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- AVXDKPABPXSLIZ-UHFFFAOYSA-M sodium;3-hydroxypropanoate Chemical compound [Na+].OCCC([O-])=O AVXDKPABPXSLIZ-UHFFFAOYSA-M 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 230000010148 water-pollination Effects 0.000 description 2
- LZDDXRWBWZUFHD-ODZAUARKSA-N (z)-but-2-enedioic acid;2-methylprop-1-ene Chemical compound CC(C)=C.OC(=O)\C=C/C(O)=O LZDDXRWBWZUFHD-ODZAUARKSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- JPAOMENBKRZQDR-UHFFFAOYSA-N CC=CC.[Na] Chemical compound CC=CC.[Na] JPAOMENBKRZQDR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000009514 concussion Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- QDPMLKBAQOZXEF-UHFFFAOYSA-N ethanesulfonic acid;sodium Chemical compound [Na].CCS(O)(=O)=O QDPMLKBAQOZXEF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920005996 polystyrene-poly(ethylene-butylene)-polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Chemical class 0.000 description 1
- 239000001267 polyvinylpyrrolidone Chemical class 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical group CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3857—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur having nitrogen in addition to sulfur
Abstract
The invention discloses a kind of polyurethane based water-based coating hyper-dispersants and preparation method thereof, the preparation method of the water paint hyper-dispersant includes: that Cyanuric Chloride is first reacted with sulfamic acid compound or hydroxyl sulfoacid compound, then it is reacted with dihydric alcohol or alcohol ammoniate, production contains sulfonic binary alcohol intermediate, this last binary alcohol intermediate reacts production polyurethane hyper-dispersant with diisocyanate, diatomic alcohol compounds in a solvent.Polyurethane hyper-dispersant prepared by the present invention can be used for high solid content water coating, and good fluidity, stability is high, bright-colored；Hyper-dispersant raw material of the present invention is cheap and easily-available, and preparation process is simple, and reaction can carry out at a lower temperature, no waste water and gas discharge.
Description
Technical field
The invention belongs to painting fields, and in particular to a kind of polyurethane based water-based coating hyper-dispersant and its preparation
Method.
Background technique
Coating refers to be coated in body surface with specific construction method after, it is cured be formed in body surface it is certain strong
The continuous protective film of degree, or it is formed with a kind of fine chemical product of certain specific function film.
Coating is generally made of film forming matter, solvent, pigment and auxiliary agent.Film forming matter is also known as base-material, is to keep coating secured
It is attached to the main matter that continuous film is formed on coated body surface；Solvent is volatile ingredient, mainly have organic solvent and
Water；Pigment is dispersed in the insoluble fine particle in paint vehicle, can be divided into coloring pigment and extender pigment, be mainly used for
Color provides protection, decorates and reduce cost；Auxiliary agent share very little shared in formulation for coating material, but play a key role.
Storage, construction, film forming and the tolerance performance of auxiliary agent coating suffer from most important effect.There is common auxiliary agent in coating: levelling
Agent, thickener, surfactant, pigment dispersing agent, plasticizer, drier, curing agent and fungicide, mould inhibitor etc..
Pigment dispersing agent also becomes wetting dispersing agent, and common pigment dispersing agent mainly has inorganic, surfactant-based
And high score subclass, effect preferably high score subclass, therefore high score subclass dispersing agent is also commonly referred to as hyper-dispersant.High score subclass includes
Natural polymer is mainly used for solvent reducible coatings；Synthesis macromolecule have polycarboxylate, polyacrylate, poly-methyl acrylate,
Maleic acid-isobutene (or styrene) copolymer salt, polyvinylpyrrolidone, polyether derivative etc..
Described in patent CN2008102009611 a kind of pigment dispersant by based on salicyclic acid derivatives and
Preparation method and application；A kind of dispersing agent and preparation method thereof is described in patent CN201110235613X, method is to adopt
Ring-opening polymerisation under the action of sodium alkoxide with anacardol and styrene oxide obtains after intermediate product same ethylene oxide polymerization again, system
It is standby gone out a kind of pigment hyper-dispersant；Patent CN2012105602412 discloses a kind of waterborne pigment dispersant, with apple
Further polycondensation based on the product that is reacted with polyethylene oxide of acid and obtain.Patent CN2007100241525 describe it is a kind of with
Methyl n-butyl ketone is solvent, is the hyperbranched non-ionic water dispersing agent of raw material with all kinds of diisocyanate, branched polyester and polyethers；
Patent CN2005800303658 describe it is a kind of using itaconic acid, the polyoxyethylene ester of citric acid and (methyl) acrylic acid as raw material,
By the dispersing agent of free-radical polymerized preparation, but this dispersing agent is used primarily in cement dispersion and cement water reducing agent field；
Patent CN2007100241525 describes a kind of preparation method of hyperbranched non-ionic dispersing agent, and raw materials are over-expense
Change polyester, diisocyanate cpd and polyethers etc.；
CN201080054508 describes a kind of preparation method of cation-type water-thinned coating dispersant.Its specific method is
It is made by polyacrylic-maleic copolymer and hydrophily primary amine reaction；CN201110119702.8, which is reported, a kind of utilizes third
The water that the monomers such as olefin(e) acid, methacrylic acid and methylpropene sodium sulfonate, 2- acrylamide-2-methyl propane sulfonic are copolymerized
Property coating dispersion preparation method；CN2007800190165 reports a kind of various unsaturated monomers of utilization, such as: maleic acid is poly-
Ether monoesters, acrylic acid, maleic anhydride etc. carry out a kind of free-radical polymerized obtained aqueous coating dispersant of nonionic.
Patent 201511016207.9, which describes, a kind of utilizes water prepared by epoxy resin, alkyl alcoholamine and phosphorus oxychloride
Property dispersible pigment color paste hyper-dispersant.
Summary of the invention
In view of the deficiencies of the prior art, the present invention provides a kind of polyurethane based water-based coating hyper-dispersant and its preparation side
Method, using water paint prepared by this dispersing agent, solid content is high, good fluidity, and stability is high, bright-colored；This product
Raw material is cheap and easily-available, and preparation process is simple, and reaction can carry out at a lower temperature, discharges substantially without waste water and gas.
The present invention is achieved by the following technical solutions:
A kind of polyurethane based water-based coating hyper-dispersant, the hyper-dispersant are prepared from the following raw materials: trichloro-triazine,
Sulfoacid compound, diisocyanate cpd, diatomic alcohol compounds, alcohol amine compound, wherein trichloro-triazine and sulfonic acid chemical combination
The molar ratio of object is 1:1, and the molar ratio of trichloro-triazine and diisocyanate cpd is 1:1~2:1.
Further, the sulfoacid compound is sulfamic acid compound or hydroxyl sulfoacid compound；The sulfamic acid
Compound includes tarine, Homotaurine；The hydroxyl sulfoacid compound includes ethylenehydrinsulfonic acid, 3- hydroxyl third
Sulfonic acid.
Further, the diisocyanate cpd is toluene di-isocyanate(TDI), '-diphenylmethane diisocyanate, different Buddhist
That ketone diisocyanate or hexamethylene diisocyanate.
Further, the diatomic alcohol compounds be ethylene glycol, 1,3-PD, 1,2-PD, 1,4-butanediol, 1,
5- pentanediol, 1,6-HD, 1,4- cyclohexanedimethanol or neopentyl glycol.
Further, the alcohol amine compound is carbinolamine, ethanol amine, n-propanolamine or n-butanol amine.
A kind of preparation method of polyurethane based water-based coating hyper-dispersant, comprising the following steps:
In a solvent, trichloro-triazine reacts step 1) with sulfoacid compound, and 2- is made and replaces -4,6- dichloro s-triazine
Object is closed, as intermediate I；
Step 2) step 1) the intermediate I, reacts with diatomic alcohol compounds or alcohol amine compound in a solvent, is made two
Hydroxy compounds, as intermediate II；
Step 3) step 2) the intermediate II and diisocyanate cpd and diatomic alcohol compounds in a solvent, with two
Dibutyl tin laurate reaction, ultimately produces the polyurethane based water-based coating hyper-dispersant.
Further, the step 1) solvent be water, acetonitrile, acetone, Isosorbide-5-Nitrae-dioxane, n,N-Dimethylformamide,
Tetrahydrofuran or DMAC N,N' dimethyl acetamide；Step 2) the solvent is acetonitrile, acetone, 1,4- dioxane, N, N- dimethyl
Formamide, tetrahydrofuran or DMAC N,N' dimethyl acetamide；Step 3) the solvent is acetonitrile, acetone, 1,4- dioxane, acetic acid
Ethyl ester, N,N-dimethylformamide, tetrahydrofuran or DMAC N,N' dimethyl acetamide.
Further, in step 2), intermediate I is 1:2 with the molar ratio of diatomic alcohol compounds or alcohol amine compound；Step
3) in, the amount of the substance of diisocyanate cpd: (amount of amount+diatomic alcohol compounds substance of the substance of intermediate II)=
1:1~1:2.
Further, the reaction temperature of step 1) is 0~5 DEG C；The reaction temperature of step 2) is 30~95 DEG C.
Beneficial effects of the present invention are as follows:
Using polyurethane resin by it as hydrophobic parts, polyamino methyl esters and s-triazine structure in resin can be mentioned
For enough " anchor point " in conjunction with granules of pigments, further by the polyoxyethylene ether segment on side chain, as water soluble group,
The hydrophily ability for improving macromolecular, in addition, improving the resistance to pH value of dispersing agent as hydrophilic radical using polyether segment
Energy.Using water paint prepared by this dispersing agent, solid content is high, good fluidity, and stability is high, bright-colored；This product
Raw material is cheap and easily-available, and preparation process is simple, and reaction can carry out at a lower temperature, discharges substantially without waste water and gas.
Specific embodiment
The present invention is further elaborated below with reference to embodiment, but the present invention is not limited thereto.
A kind of polyurethane based water-based coating hyper-dispersant, raw material include trichloro-triazine, sulfoacid compound (sulfamic acid
Compound or hydroxyl sulfoacid compound), diisocyanate cpd, diatomic alcohol compounds, alcohol amine compound.
Preparation method is as follows:
Step 1: trichloro-triazine (Cyanuric Chloride) and sulfamic acid compound or hydroxyl sulfoacid compound etc. in a solvent
Reaction, preparation 2- replace -4,6- dichloro s-triazine compound, and as intermediate I, reaction equation is as follows:
In formula: M is O or NH；N is 2 or 3.
Step 2: intermediate I and carbinolamine, ethanol amine, n-propanolamine, ethylene glycol, propylene glycol, 1,4- cyclohexanedimethanol etc.
In a solvent, 30~90 DEG C of reactions generate dihydroxy compounds, and as intermediate II, reaction equation is as follows:
In formula: M is O or NH；M is 1,2,3 or 4；N is 2 or 3；
R is-OCH2CH2,-OCH2CH2CH2,-NHCH2,-NHCH2CH2,-
NHCH2CH2CH2-。
Step 3: intermediate II and diisocyanate cpd (OCN-R2- NCO), diatomic alcohol compounds (HO-R3- OH) etc.
In a solvent, it is reacted with dibutyl tin dilaurate, generates polyurethane hyper-dispersant, reaction equation is as follows:
In formula: M is O or NH；M is 1,2,3 or 4；N is 2 or 3；
R is-OCH2CH2,-OCH2CH2CH2,-NHCH2,-NHCH2CH2,-
NHCH2CH2CH2-；
OCN-R2- NCO are as follows: toluene di-isocyanate(TDI), '-diphenylmethane diisocyanate, isophorone diisocyanate, six
Methylene diisocyanate；
HO-R3- OH are as follows: ethylene glycol, 1,3- propylene glycol, 1,2- propylene glycol, 1,4- butanediol, 1,5- pentanediol, 1,6- oneself
Glycol, 1,4- cyclohexanedimethanol, neopentyl glycol.
In the first step reaction, solvent can be water, acetonitrile, acetone, Isosorbide-5-Nitrae-dioxane, n,N-Dimethylformamide
(DMF), tetrahydrofuran (THF), DMAC N,N' dimethyl acetamide (DMAC) etc..
The temperature of the first step reaction is 0~5 DEG C.
The molar ratio of trichloro-triazine and sulfamic acid compound or hydroxyl sulfoacid compound is in the first step reaction
1:1。
In the second step reaction, solvent can be acetonitrile, acetone, Isosorbide-5-Nitrae-dioxane, n,N-Dimethylformamide
(DMF), tetrahydrofuran (THF), DMAC N,N' dimethyl acetamide (DMAC) etc..
The temperature of the second step reaction is 30~95 DEG C.
In the second step reaction, intermediate I and carbinolamine, ethanol amine, n-propanolamine, ethylene glycol, propylene glycol, Isosorbide-5-Nitrae-ring
The molar ratio of own dimethanol is 1:2.
In the third step reaction, solvent can be acetonitrile, acetone, Isosorbide-5-Nitrae-dioxane, ethyl acetate, N, N- dimethyl
Formamide (DMF), tetrahydrofuran (THF), DMAC N,N' dimethyl acetamide (DMAC) etc..
In the third step reaction, the amount of the substance of diisocyanate cpd: (amount+binary of the substance of intermediate II
The amount of the substance of alcoholic compound)=1:1~1:2.
Embodiment 1
(1) the 3- hydroxy-propanesulfonic acid of 0.1mol is neutralized with sodium hydroxide, prepares 3- hydroxypropionate sodium solid powder.?
In four-hole boiling flask, 300mL acetonitrile and 0.1mol Cyanuric Chloride is added, ice salt bath is cooled to 5 DEG C, and side stirring, side slowly adds in batches
Enter 3- hydroxypropionate sodium, and control reaction system pH=9 with the acetonitrile solution of a small amount of triethylamine, terminates after reacting 3h, obtain
The acetonitrile solution of intermediate I.Intermediate I (1) structural formula is as follows:
(2) ethanol amine 0.2mol is added into the acetonitrile solution (30mL) of intermediate I containing 0.1mol (1), is warming up to 30 DEG C,
2h is reacted, continues to be warming up to 80 DEG C, reacts 3h, obtain the acetonitrile solution of intermediate II.
Intermediate II (1) structural formula is as follows:
(3) isophorone diisocyanate is added into the acetonitrile solution (60mL) of intermediate II containing 0.05mol (1)
0.15mol and ethylene glycol 0.1mol, and a few drop dibutyl tin dilaurates are added, it stirs, is warming up to 80 DEG C, after reacting 3h, rotation
Turn evaporation and remove acetonitrile, obtains 1 solid powder of polyurethane hyper-dispersant, structural formula is as follows:
Embodiment 2
(1) ethylenehydrinsulfonic acid of 0.1mol is neutralized with sodium hydroxide, prepares ethylenehydrinsulfonic acid sodium solid powder.At four mouthfuls
In flask, 100mLDMF and 0.1mol Cyanuric Chloride is added, ice salt bath is cooled to 5 DEG C, and side stirring, side is slowly added to hydroxyl in batches
Ethanesulfonic acid sodium, and reaction system pH=9 is controlled with the DMF solution of a small amount of triethylamine, terminate after reacting 3h, obtains intermediate I
DMF solution.Intermediate I (2) structural formula is as follows:
(2) n-propanolamine 0.2mol is added into the DMF solution of intermediate I containing 0.1mol (2), is warming up to 20 DEG C, reaction
2h continues to be warming up to 90 DEG C, reacts 3h, obtain the DMF solution of intermediate II (2).Intermediate II (2) structural formula is as follows:
(3) '-diphenylmethane diisocyanate is added into the DMF solution (60mL) of intermediate II containing 0.2mol (2)
0.15mol and 1,3-PD 0.1mol, and a few drop dibutyl tin dilaurates are added, it stirs, is warming up to 80 DEG C, react 3h
Afterwards, rotary evaporation removes DMF, obtains 2 solid powder of polyurethane hyper-dispersant, structural formula is as follows:
Embodiment 3
Operating method such as embodiment 2.For the raw material that first step operation uses for Homotaurine, reaction dissolvent is Isosorbide-5-Nitrae-
Dioxane obtains intermediate I (3), and reaction temperature is 0 DEG C；It is Isosorbide-5-Nitrae-cyclohexanedimethanol, reaction dissolvent that second step, which reacts drug,
For Isosorbide-5-Nitrae-dioxane, intermediate I (3) and Isosorbide-5-Nitrae-cyclohexanedimethanol molar ratio are 1:2,80 DEG C of reaction temperature；Third step is anti-
Answering drug is hexamethylene diisocyanate (0.5mol), second step reaction product intermediate II (3) (0.3mol) and 1,4- ring
Own dimethanol (0.3mol), reaction dissolvent are Isosorbide-5-Nitrae-dioxane (500mL), and reaction temperature is 80 DEG C, and final products are poly- ammonia
Ester group hyper-dispersant 3, structural formula is as follows:
Embodiment 4
Operating method such as embodiment 2.The raw material that first step operation uses is 3- hydroxy-propanesulfonic acids, reaction dissolvent third
Ketone, reaction product are intermediate I (1)；It is 1,2-PD that second step, which reacts drug, and reaction dissolvent is acetone, intermediate I (1)
It is 1:2 with 1,2-PD molar ratio, this step reaction product is intermediate II (4)；It is toluene diisocyanate that third step, which reacts drug,
Acid esters (1mol), intermediate II (4) (1mol) and 1,2-PD (0.7mol), reaction dissolvent are acetone, reaction temperature 80
DEG C, final products are polyurethane hyper-dispersant 4, and structural formula is as follows:
Embodiment 5
Operating method such as embodiment 2.For the raw material that first step operation uses for Homotaurine, reaction dissolvent is water,
0 DEG C of reaction temperature, the first step after reaction, be evaporated under reduced pressure remove moisture, obtain intermediate I (3)；Second step reacts drug
1,3-PD, reaction dissolvent DMAC obtain intermediate II (5)；It is isophorone diisocyanate that third step, which reacts drug,
(0.2mol), intermediate II (5) (0.15mol) and neopentyl glycol (0.15mol), reaction dissolvent is DMAC (200mL), final to produce
Product are polyurethane hyper-dispersant 5.
Embodiment 6
Operating method such as embodiment 2.For 3- hydroxy-propanesulfonic acid, reaction dissolvent is the raw material that first step operation uses
DMAC, obtains intermediate I (1) by 5 DEG C of reaction temperature；It is 1,2-PD that second step, which reacts drug, and reaction dissolvent is acetone, 90 DEG C
3h is reacted, intermediate II (6) are obtained；It is toluene di-isocyanate(TDI) (0.7mol), intermediate II (6) that third step, which reacts drug,
(0.3mol) and Isosorbide-5-Nitrae-cyclohexanedimethanol (0.4mol), reaction dissolvent are acetone (300mL), and final products are polyurethane oversubscription
Powder 6.
Embodiment 7
Operating method such as embodiment 2.The raw material that first step operation uses is 2- ethylenehydrinsulfonic acids, reaction dissolvent THF,
It obtains intermediate I (2)；It is Isosorbide-5-Nitrae-cyclohexanedimethanol that second step, which reacts drug, and reaction dissolvent is that THF obtains intermediate II (7)；Third step
Reaction drug is hexamethylene diisocyanate (1.2mol), intermediate II (7) (1mol) and 1,5-PD (1mol), reaction
Solvent is THF, and final products are polyurethane hyper-dispersant 7.
Embodiment 8
Operating method such as embodiment 2.The raw material that first step operation uses is 2- ethylenehydrinsulfonic acids, reaction dissolvent DMF,
It obtains intermediate I (2)；It is n-propanolamine that second step, which reacts drug, and reaction dissolvent DMF, 40 DEG C of reaction 5h obtain intermediate II (2)；
Third step react drug be toluene di-isocyanate(TDI) (1mol), intermediate II (2) (0.8mol) and 1,6- hexylene glycol (0.6mol),
Reaction dissolvent is DMF (200mL), and 90 DEG C of reaction temperature, final products are polyurethane hyper-dispersant 8.
Embodiment 9
Operating method such as embodiment 2.For the raw material that use of first step operation for 2-aminoethanesulfonic acid, reaction dissolvent is water, 0
DEG C reaction 2h, the first step after reaction, be evaporated under reduced pressure remove moisture, obtain intermediate I (9)；It is first that second step, which reacts drug,
Hydramine (2mol) and intermediate I (9) (1mol), reaction dissolvent are acetone, and 30 DEG C of reaction 3h obtain intermediate II (9)；Third step is anti-
Answering drug is '-diphenylmethane diisocyanate (0.1mol), intermediate II (9) (0.05mol) and 1,3-PD
(0.075mol), reaction dissolvent are acetone, and 70 DEG C of reaction temperature, final products are polyurethane hyper-dispersant 9.
Embodiment 10
Operating method such as embodiment 2.For the raw material that first step operation uses for 3- hydroxy-propanesulfonic acid, reaction dissolvent is Isosorbide-5-Nitrae-
Dioxane；It is ethanol amine, reaction dissolvent DMAC that second step, which reacts drug,；It is two isocyanide of isophorone that third step, which reacts drug,
Acid esters (3mol), second step product (2.5mol) and 1,2-PD (1.5mol), reaction dissolvent are acetone (2000mL), reaction
75 DEG C of temperature, final products are polyurethane hyper-dispersant 10.
Test case 1
Water polyurethane base hyper-dispersant, organic pigment and water obtained are weighed according to the proportion of table 1 and concussion is added
Cup is uniformly mixed, after vibrating 3h on the oscillator under room temperature, then phases such as the viscosity of test sample, tinting strength, tinting power and covering power
Performance parameter is closed, test result is shown in Table 2.
1 hyper-dispersant test formulations of table
2 hyper-dispersant of table preparation washing color paste viscosity (25 DEG C)
Claims (9)
1. a kind of polyurethane based water-based coating hyper-dispersant, which is characterized in that the hyper-dispersant is prepared from the following raw materials: three
Chloro-s-triazine, sulfoacid compound, diisocyanate cpd, diatomic alcohol compounds, alcohol amine compound, wherein trichloro-triazine
It is 1:1 with the molar ratio of sulfoacid compound, the molar ratio of trichloro-triazine and diisocyanate cpd is 1:1 ~ 2:1.
2. a kind of polyurethane based water-based coating hyper-dispersant according to claim 1, which is characterized in that described sulfonated
Closing object is sulfamic acid compound or hydroxyl sulfoacid compound；The sulfamic acid compound includes tarine, 3- amino
Propane sulfonic acid；The hydroxyl sulfoacid compound includes ethylenehydrinsulfonic acid, 3- hydroxy-propanesulfonic acid.
3. a kind of polyurethane based water-based coating hyper-dispersant according to claim 1, which is characterized in that two isocyanide
Ester compound is toluene di-isocyanate(TDI), '-diphenylmethane diisocyanate, isophorone diisocyanate or hexa-methylene two
Isocyanates.
4. a kind of polyurethane based water-based coating hyper-dispersant according to claim 1, which is characterized in that the dihydric alcohol
Compound is ethylene glycol, 1,3- propylene glycol, 1,2- propylene glycol, 1,4- butanediol, 1,5- pentanediol, 1,6-HD, 1,4- ring
Own dimethanol or neopentyl glycol.
5. a kind of polyurethane based water-based coating hyper-dispersant according to claim 1, which is characterized in that the alcohol amination
Conjunction object is carbinolamine, ethanol amine, n-propanolamine or n-butanol amine.
6. a kind of preparation method of polyurethane based water-based coating hyper-dispersant described in claim 1, which is characterized in that including
Following steps:
In a solvent, trichloro-triazine reacts step 1) with sulfoacid compound, and 2- is made and replaces -4,6- dichloro s-triazine chemical combination
Object, as intermediate I；
Intermediate I described in step 2 step 1), reacts with diatomic alcohol compounds or alcohol amine compound in a solvent, and dihydroxy is made
Compound, as intermediate II；
Intermediate II described in step 3) step 2 and diisocyanate cpd and diatomic alcohol compounds in a solvent, with two laurels
Sour dibutyl tin reaction, ultimately produces the polyurethane based water-based coating hyper-dispersant.
7. a kind of preparation method of polyurethane based water-based coating hyper-dispersant according to claim 6, which is characterized in that
Solvent described in step 1) is water, acetonitrile, acetone, 1,4- dioxane, N,N-dimethylformamide, tetrahydrofuran or N, N- diformazan
Yl acetamide；
Solvent described in step 2 is acetonitrile, acetone, 1,4- dioxane, N,N-dimethylformamide, tetrahydrofuran or N, N- bis-
Methylacetamide；
Solvent described in step 3) is acetonitrile, acetone, 1,4- dioxane, ethyl acetate, N,N-dimethylformamide, tetrahydrofuran
Or DMAC N,N' dimethyl acetamide.
8. a kind of preparation method of polyurethane based water-based coating hyper-dispersant according to claim 6, which is characterized in that
In step 2, intermediate I is 1:2 with the molar ratio of diatomic alcohol compounds or alcohol amine compound；In step 3), diisocyanate esterification
Close the amount of the substance of object: (amount of amount+diatomic alcohol compounds substance of the substance of intermediate II)=1:1 ~ 1:2.
9. a kind of preparation method of polyurethane based water-based coating hyper-dispersant according to claim 6, which is characterized in that
The reaction temperature of step 1) is 0 ~ 5 DEG C；The reaction temperature of step 2 is 30 ~ 95 DEG C.
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| CN112430447A (en) * | 2020-11-25 | 2021-03-02 | 保定邦泰高分子新材料有限公司 | Waterborne polyurethane adhesive for shoes and preparation process thereof |
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|---|---|---|---|---|
| CN1310205A (en) * | 2000-01-20 | 2001-08-29 | 大日精化工业株式会社 | Pigment dispersing agent and pigment composition containing the same dispersing agent |
| CN1343666A (en) * | 2000-09-21 | 2002-04-10 | 王建国 | Monochloro-sym-triazine derivative and its application |
| CN105949349A (en) * | 2016-05-11 | 2016-09-21 | 南京晓庄学院 | Chitosan-based hyperdispersant and preparation method thereof |
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|---|---|---|---|---|
| CN1310205A (en) * | 2000-01-20 | 2001-08-29 | 大日精化工业株式会社 | Pigment dispersing agent and pigment composition containing the same dispersing agent |
| CN1343666A (en) * | 2000-09-21 | 2002-04-10 | 王建国 | Monochloro-sym-triazine derivative and its application |
| CN105949349A (en) * | 2016-05-11 | 2016-09-21 | 南京晓庄学院 | Chitosan-based hyperdispersant and preparation method thereof |
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| CN112430447A (en) * | 2020-11-25 | 2021-03-02 | 保定邦泰高分子新材料有限公司 | Waterborne polyurethane adhesive for shoes and preparation process thereof |
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Address after: 224403 shuangchang Avenue, Aoyang Industrial Park, Funing County, Yancheng City, Jiangsu Province Patentee after: LIWANG (JIANGSU) Co.,Ltd. Address before: 224000 shuangchang Avenue, Aoyang Industrial Park, Funing County, Yancheng City, Jiangsu Province Patentee before: JIANGSU LI WANG TECHNOLOGY CO.,LTD. |