CN101117450A - Preparation method of non-ionic hyperbranched macromolecular dispersant for organic pigment - Google Patents
Preparation method of non-ionic hyperbranched macromolecular dispersant for organic pigment Download PDFInfo
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- CN101117450A CN101117450A CNA2007100241525A CN200710024152A CN101117450A CN 101117450 A CN101117450 A CN 101117450A CN A2007100241525 A CNA2007100241525 A CN A2007100241525A CN 200710024152 A CN200710024152 A CN 200710024152A CN 101117450 A CN101117450 A CN 101117450A
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- China
- Prior art keywords
- hyperbranched
- ionic
- solvent
- preparation
- organic pigment
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- 239000002270 dispersing agent Substances 0.000 title claims abstract description 62
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 239000012860 organic pigment Substances 0.000 title claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 46
- 229920000587 hyperbranched polymer Polymers 0.000 claims abstract description 28
- 238000001816 cooling Methods 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 238000003756 stirring Methods 0.000 claims abstract description 17
- 238000002156 mixing Methods 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 3
- 238000001291 vacuum drying Methods 0.000 claims abstract description 3
- 238000005406 washing Methods 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 49
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 239000008367 deionised water Substances 0.000 claims description 25
- 229910021641 deionized water Inorganic materials 0.000 claims description 25
- 238000009736 wetting Methods 0.000 claims description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- -1 polyoxyethylene Polymers 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 14
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 14
- 239000010695 polyglycol Substances 0.000 claims description 14
- 229920000151 polyglycol Polymers 0.000 claims description 14
- 238000001556 precipitation Methods 0.000 claims description 14
- 229920000728 polyester Polymers 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 238000013019 agitation Methods 0.000 claims description 10
- 238000009413 insulation Methods 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 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 description 8
- 239000012046 mixed solvent Substances 0.000 claims description 8
- 229920001610 polycaprolactone Polymers 0.000 claims description 8
- 239000004632 polycaprolactone Substances 0.000 claims description 8
- 238000002390 rotary evaporation Methods 0.000 claims description 8
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical group CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 6
- 239000003921 oil Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 4
- 229940043276 diisopropanolamine Drugs 0.000 claims description 4
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
- 229920003055 poly(ester-imide) Polymers 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 claims description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 3
- BCNBMSZKALBQEF-UHFFFAOYSA-N 1,3-dimethylpyrrolidin-2-one Chemical compound CC1CCN(C)C1=O BCNBMSZKALBQEF-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000004697 Polyetherimide Substances 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 229920002396 Polyurea Polymers 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 2
- 229920001643 poly(ether ketone) Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- 229920003257 polycarbosilane Polymers 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 229920001601 polyetherimide Polymers 0.000 claims description 2
- 229920006389 polyphenyl polymer Polymers 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- 229910000077 silane Inorganic materials 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 2
- 229960004418 trolamine Drugs 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- OSNIIMCBVLBNGS-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-(dimethylamino)propan-1-one Chemical compound CN(C)C(C)C(=O)C1=CC=C2OCOC2=C1 OSNIIMCBVLBNGS-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 abstract description 6
- 230000002209 hydrophobic effect Effects 0.000 abstract description 4
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 239000007822 coupling agent Substances 0.000 abstract 2
- 238000004321 preservation Methods 0.000 abstract 2
- 230000001133 acceleration Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 54
- 239000000049 pigment Substances 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 14
- 238000009835 boiling Methods 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 230000003252 repetitive effect Effects 0.000 description 6
- 238000005201 scrubbing Methods 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 239000002245 particle Substances 0.000 description 5
- 239000000975 dye Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YVSNBDFDMHIXBF-UHFFFAOYSA-N 1-(chloromethylsulfanyl)dodecane Chemical compound CCCCCCCCCCCCSCCl YVSNBDFDMHIXBF-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 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 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- NWGKJDSIEKMTRX-MDZDMXLPSA-N Sorbitan oleate Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OCC(O)C1OCC(O)C1O NWGKJDSIEKMTRX-MDZDMXLPSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 2
- HVUMOYIDDBPOLL-UHFFFAOYSA-N 2-(3,4-Dihydroxyoxolan-2-yl)-2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)C1OCC(O)C1O HVUMOYIDDBPOLL-UHFFFAOYSA-N 0.000 description 1
- IJCWFDPJFXGQBN-UHFFFAOYSA-N 2-[4-Hydroxy-3-(octadecanoyloxy)oxolan-2-yl]-2-(octadecanoyloxy)ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)C1OCC(O)C1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-UHFFFAOYSA-N 0.000 description 1
- CXRFDZFCGOPDTD-UHFFFAOYSA-M Cetrimide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)C CXRFDZFCGOPDTD-UHFFFAOYSA-M 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical class N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 229920002642 Polysorbate 65 Polymers 0.000 description 1
- 229920002651 Polysorbate 85 Polymers 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 1
- LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- 229940057847 polyethylene glycol 600 Drugs 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 229940099511 polysorbate 65 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940113171 polysorbate 85 Drugs 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- ITCAUAYQCALGGV-XTICBAGASA-M sodium;(1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound [Na+].C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C([O-])=O ITCAUAYQCALGGV-XTICBAGASA-M 0.000 description 1
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 1
- PRXRUNOAOLTIEF-WUOFIQDXSA-N sorbitan trioleate Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C\CCCCCCCC)C1OCC(O)C1OC(=O)CCCCCCC\C=C\CCCCCCCC PRXRUNOAOLTIEF-WUOFIQDXSA-N 0.000 description 1
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
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- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
The invention relates to a preparation method of non-ionic hyperbranched macromolecular dispersing agent for organic pigment belonging to the fine chemical field. The invention mainly adopts hydrophobic hyperbranched polymer, coupling agent and hydrophilic chain which are respectively dissolved in solvent to be made into solution through complete dissolving and even mixing; coupling agent solvent solution is added in a reaction vessel and warms up through stirring; hydrophilic chain solvent solution is also added in the reaction vessel for stirring and heat preservation reaction; and then, hydrophobic hyperbranched polymer solvent solution is added to complete warming-up and heat preservation reaction through stirring; finally, the non-ionic hyperbranched macromolecular dispersing agent is obtained after cooling, filtration, washing and vacuum drying. The invention can make nanometer organic dye with high solid content, ideal liquidity, high stability and fresh color; meanwhile, the invention has the advantages of simple technical process, reaction being completed at lower temperature, convenient purification of products and non-occurrence of gel and automatic acceleration phenomena.
Description
Technical field
The present invention relates to a kind of preparation method of non-ionic hyperbranched macromolecular dispersant for organic pigment, belong to field of fine chemical.
Background technology
Pigment mainly is to exist with forms such as aggregate, aggregate or flocs units, and particle causes the bright-colored degree and the luminance range of pigment than thick and skewness.In addition, pigment has only evenly, stably is dispersed in the medium as a kind of tinting material, could bring into play its pigmentation preferably.Therefore, the super-refinement of pigment and stably dispersing are the prerequisites of its widespread use.Especially after pigment particle size was reduced to nano-scale, every physical and chemical performance all was significantly improved.Yet along with reducing of pigment particle size, the surface of pigments free energy is but increasing, and it is unstable that system becomes, and the tendency that reduces surface-area automatically increases, and this tendency shows as flocculation, cohesion, gathering and the crystalline growth of pigment.Thereby cause pigment particle size increase, bad stability.
Address the above problem, generally adopt nonionic, negatively charged ion, cats product and some low molecules or polymer confrontation pigment particles surface to carry out modification at present.By deposition on surface of pigments or coat unit molecule or the derivative of polymolecular material such as tensio-active agent, properties-correcting agent, pigment itself etc., can change the surface polarity of pigment.In recent years, hyper-dispersant (Hyper-dispersants) is because its special structure and performance become the research focus that surface of pigments is processed, and Xiang Guan patent and bibliographical information are more therewith.People such as C Ao Shila, E Eckstein disclose a kind of segmented copolymer dispersion agent; People such as MASHEAU-HWA disclose a kind of graft copolymer dispersion agent.In addition, United States Patent (USP) and European patent have also carried out numerous reports and description to the preparation method of macromolecule dispersing agent.Although these macromolecule dispersing agents are from improving dispersing of pigments stability and mobile in varying degrees, solid content is lower, remains in some problems.How pigment dyestuff is processed into the focus that solid content height, good fluidity, stable height, brightly painted nano level dispersion system are still scientific worker's research.
Hyperbranched polymer contains highly branched structure, is the 3 D stereo shape, and there is a large amount of terminal functionality in the molecule periphery.The structure that it is highly branched, make hyperbranched polymer be difficult to crystallization, no chain twines, thereby solubility property improves greatly, compare with the linear molecule of same molecular quality, viscosity is lower, therefore, can obtain solid content height, good fluidity, stable high dispersion system with the hyperbranched polymer dispersed color.Owing to have particular structure like this and performance, make hyperbranched polymer become the important directions of 21 century polymer science research.
Summary of the invention
The objective of the invention is to overcome above-mentioned weak point, thereby provide a kind of preparation method of non-ionic hyperbranched macromolecular dispersant for organic pigment, this dispersion agent is to be that hydrophobic parts, isocyanates are coupler with the hyperbranched polymer, the polymkeric substance of grafting wetting ability chain.Adopt this dispersion agent that pigment is carried out modification, can obtain solid content height, good fluidity, stable height, brightly painted nano level pigment dyestuff.
Main solution of the present invention is achieved in that
The preparation method of non-ionic hyperbranched macromolecular dispersant for organic pigment of the present invention adopts following processing step:
1, the preparation of hydrophobicity hyperbranched polymer solvent solution, coupler solvent solution and wetting ability chain solvent solution:
Getting the hydrophobicity hyperbranched polymer is: 10～50 weight %, solvent are: 50～90 weight %, and the hydrophobicity hyperbranched polymer is dissolved in the solvent, makes hydrophobicity hyperbranched polymer solvent solution through fully dissolving;
Getting coupler is: 10～40 weight %, solvent are: 60～90 weight %, and coupler is dissolved in the solvent, makes the coupler solvent solution through fully dissolving;
Getting the wetting ability chain is: 20～50 weight %, solvent are: 50～80 weight %, and the wetting ability chain is dissolved in the solvent, makes wetting ability chain solvent solution through fully dissolving;
2, the coupler solvent solution is placed reaction vessel, under agitation heat up, temperature is: 40 ℃～60 ℃, wetting ability chain solvent solution is placed above-mentioned reaction vessel, through stirring, after the insulation reaction 1～5 hour, add hydrophobicity hyperbranched polymer solvent solution, under agitation heat up, temperature is: 50 ℃～80 ℃, insulation reaction 2～5 hours, through cooling, cooling temperature: 10 ℃～30 ℃, be cooling time: 1～2 hour again, rotary evaporation removes and desolvates, be reacting coarse product behind the evaporate to dryness, add the mixing solutions of precipitation agent and deionized water then, after filtration, washing, vacuum-drying 12～24 hours was non-ionic hyperbranched macromolecular dispersant, and vacuum tightness is: 0.01Mpa～0.1Mpa.
The mol ratio of coupler of the present invention and wetting ability chain is 2.1～0.9: 1; The mol ratio of hydrophobicity hyperbranched polymer and wetting ability chain is 1: 20～40;
The mass ratio of precipitation agent of the present invention and deionized water is 1: 4～4: 1, and the mixing solutions consumption of precipitation agent and deionized water is 10～20 times of reacting coarse product total mass;
Non-ionic hyperbranched macromolecular dispersant of the present invention is dissolved in the deionized water, makes non-ionic hyperbranched macromolecular dispersant solution, and concentration is: 10g/L～100g/L.
The present invention is re-dubbed non-ionic hyperbranched macromolecular dispersant solution with the non-ionic hyperbranched macromolecular dispersant and the low-molecular-weight surfactant of preparation.
The mass ratio of low-molecular-weight surfactant of the present invention and non-ionic hyperbranched macromolecular dispersant is 5: 1～1: 5.
Hydrophobicity hyperbranched polymer of the present invention is a kind of in aromatic series hyper-branched polyester, aliphatics hyper-branched polyester, hyperbranched poly ester-acid amide, hyper-branched polyester-amine, hyper-branched polyester-imide, hyperbranched polyether, hyperbranched polyether ketone, hyperbranched polyether imide, hyperbranched polyphenyl, hyperbranched polyamine, ultrabranching polyamide, hyperbranched polyureas, hyperbranched poly silica silane or the hyperbranched Polycarbosilane.
Wetting ability chain of the present invention is polyoxyethylene glycol-600, polyoxyethylene glycol-800, polyoxyethylene glycol-1000, polyoxyethylene glycol-2000, polyoxyethylene glycol-4000, poly glycol monomethyl ether-500, poly glycol monomethyl ether-750, poly glycol monomethyl ether-1000, poly glycol monomethyl ether-2500, poly glycol monomethyl ether-5000, polyvinyl acetal, polycaprolactone single-acrylate, trolamine, tri-isopropanolamine, diisopropanolamine (DIPA), N, one or both mixtures in N-dimethyl propanol amine, the 2 hydroxy propanoic acid.
Coupler of the present invention is 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,4-ethylbenzene vulcabond, 4,4 '-diphenylmethanediisocyanate, 1,5-naphthalene diisocyanate, hexa-methylene 1,6-two isocyanic acids, 4, a kind of or two kinds of mixtures in 4 '-dicyclohexyl methane diisocyanate.
Solvent of the present invention is one or more mixed solvents in ethyl acetate, n-butyl acetate, methylene dichloride, chloroform, tetracol phenixin, acetone, butanone, methyl n-butyl ketone, pyrrolidone, methyl-2-pyrrolidone, dimethyl pyrrolidone, dimethyl sulfoxide (DMSO), dimethyl formamide, TriMethylolPropane(TMP), the tetrahydrofuran (THF).
Precipitation agent of the present invention is one or more mixtures in methyl alcohol, ethanol, propyl alcohol, Virahol, propyl carbinol, propyl carbinol, isopropylcarbinol, water, ether, dipropyl ether, methyl-phenoxide, hexanaphthene, methylcyclohexane, sherwood oil, benzene,toluene,xylene, the ethylbenzene.
Low-molecular-weight surfactant of the present invention is an anion surfactant as potassium oleate, sodium abietate, sodium lauryl sulphate, Sodium dodecylbenzene sulfonate, sodium alkyl naphthalene sulfonate; Or cats product is as dodecyl chloromethyl thioether, Trimethyllaurylammonium bromide, Tetradecyl Trimethyl Ammonium Bromide, cetyl trimethylammonium bromide, octadecyl trimethylammonium bromide, stearyl dimethyl benzyl ammonium chloride; Or nonionogenic tenside is as one or more mixtures in polysorbate60, tween 61, polysorbate65, tween 80, sorbimacrogol oleate100, polysorbate85, span 20, span 40, sorbester p18, sorbester p38, sorbester p17, sapn 83, sorbester p37, peregal A-10, paregal O-25, the peregal os-15.
Compared with the prior art the present invention has the following advantages:
The present invention is to be that hydrophobic parts, isocyanates are coupler with the hyperbranched polymer, the polymkeric substance of grafting wetting ability chain; Adopt this dispersion agent that pigment is carried out modification, can obtain solid content height, good fluidity, stable height, brightly painted nano level pigment dyestuff; Technical process is simple, reaction can be carried out under lower temperature, purification of products is convenient, gel and automatic hastening phenomenon can not occur.
Embodiment
Embodiment during following the present invention incites somebody to action in conjunction with the accompanying drawings is further described:
Embodiment one:
The preparation method of non-ionic hyperbranched macromolecular dispersant for organic pigment of the present invention adopts following processing step:
Hydrophobicity hyperbranched polymer of the present invention is got aliphatics hyper-branched polyester (M
nBeing 17600) 17.60 grams, coupler gets 2,4-tolylene diisocyanate 7.84 gram and wetting ability chain are got polycaprolactone single-acrylate (molecular-weight average is 344) 17.20 grams and are dissolved in 158.40 grams, 7.84 grams and the 68.80 gram solvent methyl n-butyl ketones fully dissolving, mixing respectively.Make aliphatics hyper-branched polyester methyl n-butyl ketone solution, 2,4 toluene diisocyanate methyl n-butyl ketone solution and polycaprolactone single-acrylate methyl n-butyl ketone solution respectively.7.24 gram 2,4 toluene diisocyanate methyl n-butyl ketone solution are placed the four-hole boiling flask that has stirring, thermometer, dropping funnel and condensing works, under agitation heat up, temperature is: 60 ℃; The methyl n-butyl ketone solution of 43.00 gram polycaprolactone single-acrylates is placed dropping funnel, slowly splash in the four-hole boiling flask, stir insulation reaction 5 hours; The methyl n-butyl ketone solution that adds 88.00 gram aliphatics hyper-branched polyesters, be warming up to 50 ℃, reacted 5 hours, cooling again, cooling temperature: 10 ℃, be cooling time: 1 hour, rotary evaporation removes the methyl n-butyl ketone that desolvates, it behind the evaporate to dryness reacting coarse product, (methyl-phenoxide is the mixed solvent of adding 462.40 gram precipitation agents (methyl-phenoxide/deionized water): 20 weight % in crude product, deionized water is: 80 weight %), make graftomer precipitate, use the cup type strainer of A-50 stainless steel (filter opening is of a size of 0.1 μ m) to filter and obtain synthetic product, with 100g/L aqueous ethanolic solution repetitive scrubbing, drying is 24 hours under the vacuum, and vacuum tightness: 0.01Mpa obtains non-ionic hyperbranched macromolecular dispersant.
Accurately weighing 10.00 gram non-ionic hyperbranched macromolecular dispersants add 100 ml deionized water, are configured to the non-ionic hyperbranched macromolecular dispersant aqueous solution of 100g/L; In the non-ionic hyperbranched macromolecular dispersant aqueous solution, add 2.00 gram octadecyl trimethylammonium bromides, obtain the combination solution of non-ionic hyperbranched macromolecular dispersant and cationic low-molecular-weight surfactant.
Embodiment two:
The preparation method of non-ionic hyperbranched macromolecular dispersant for organic pigment of the present invention adopts following processing step:
Hydrophobicity hyperbranched polymer of the present invention is got hyper-branched polyester-imide (M
nBeing 11700) 11.70 grams, coupler gets hexa-methylene 1,6-vulcabond 7.06 grams and wetting ability chain taking polyethylene glycol-1000 (molecular-weight average is 1000) 20.00 restrain and are dissolved in respectively in 11.70 grams, 63.54 grams and the 20.00 gram solvent acetone, fully dissolve, mix.Make hyper-branched polyester-imide acetone soln, hexa-methylene 1 respectively, 6-vulcabond acetone soln and polyoxyethylene glycol-600 acetone solns.With 70.60 gram hexa-methylenes 1, the acetone soln of 6-vulcabond places the four-hole boiling flask that has stirring, thermometer, dropping funnel and condensing works, under agitation heats up, and temperature is: 40 ℃; The acetone soln of 40.00 gram polyoxyethylene glycol-1000 is placed dropping funnel, slowly splash in the four-hole boiling flask, stir insulation reaction 5 hours; Add 23.40 gram hyper-branched polyester-imido acetone solns, be warming up to 50 ℃, reacted 5 hours, cooling again, cooling temperature: 30 ℃, be cooling time: 2 hours, rotary evaporation is removed solvent acetone, it behind the evaporate to dryness reacting coarse product, (sherwood oil is the mixed solvent of adding 387.60 gram precipitation agents (sherwood oil/deionized water): 80 weight % in crude product, deionized water is: 20 weight %), make graftomer precipitate, use the cup type strainer of A-50 stainless steel (filter opening is of a size of 0.1 μ m) to filter and obtain synthetic product, with 100g/L aqueous ethanolic solution repetitive scrubbing, drying is 12 hours under the vacuum, and vacuum tightness: 0.1Mpa obtains non-ionic hyperbranched macromolecular dispersant.
Accurately weighing 10.00 gram non-ionic hyperbranched macromolecular dispersants add 100 ml deionized water, are configured to the non-ionic hyperbranched macromolecular dispersant aqueous solution of 100g/L; In the non-ionic hyperbranched macromolecular dispersant aqueous solution, add 2.00 gram sodium abietates, obtain the combination solution of non-ionic hyperbranched macromolecular dispersant and anionic low-molecular-weight surfactant.
Embodiment three:
The preparation method of non-ionic hyperbranched macromolecular dispersant for organic pigment of the present invention adopts following processing step:
Hydrophobicity hyperbranched polymer of the present invention is got aromatic series hyper-branched polyester (M
nBeing 12800) 12.80 grams, coupler gets 4,4 '-diphenylmethanediisocyanate, 9.01 grams and wetting ability chain taking polyethylene glycol monomethyl ether-500 (molecular-weight average is 500) 20.00 restrain and are dissolved in respectively in 115.20 grams, 13.52 grams and the 80.00 gram solvent ethyl acetates, fully dissolve, mix.Make aromatic series hyper-branched polyester ethyl acetate solution, 4 respectively, 4 '-diphenylmethanediisocyanate ethyl acetate solution and poly glycol monomethyl ether-500 ethyl acetate solutions.With 22.53 grams 4, the ethyl acetate solution of 4 '-diphenylmethanediisocyanate places the four-hole boiling flask that has stirring, thermometer, dropping funnel and condensing works, under agitation heats up, and temperature is: 40 ℃; The ethyl acetate solution of 100.00 gram poly glycol monomethyl ethers-500 is placed dropping funnel, slowly splash in the four-hole boiling flask, stir insulation reaction 2 hours; The ethyl acetate solution that adds 128.00 gram aromatic series hyper-branched polyesters, be warming up to 80 ℃, reacted 2 hours, cooling again, cooling temperature: 30 ℃, be cooling time: 2 hours, rotary evaporation is removed solvent ethyl acetate, it behind the evaporate to dryness reacting coarse product, (dipropyl ether is the mixed solvent of adding 418.1 gram precipitation agents (dipropyl ether/deionized water): 80 weight % in crude product, deionized water is: 20 weight %), make graftomer precipitate, use the cup type strainer of A-50 stainless steel (filter opening is of a size of 0.1 μ m) to filter and obtain synthetic product, with 100g/L methanol aqueous solution repetitive scrubbing, drying is 12 hours under the vacuum, and vacuum tightness: 0.1Mpa obtains non-ionic hyperbranched macromolecular dispersant.
Accurately weighing 10.00 gram non-ionic hyperbranched macromolecular dispersants add 100 ml deionized water, are configured to the non-ionic hyperbranched macromolecular dispersant aqueous solution of 100g/L; In the non-ionic hyperbranched macromolecular dispersant aqueous solution, add 2.00 gram polysorbate65s, obtain the combination solution of non-ionic hyperbranched macromolecular dispersant and non-ionic type low-molecular-weight surfactant.
Embodiment four:
The preparation method of non-ionic hyperbranched macromolecular dispersant for organic pigment of the present invention adopts following processing step:
Hydrophobicity hyperbranched polymer of the present invention is got hyperbranched poly ester-acid amide (M
nBeing 15100) 15.10 grams, coupler gets 2,4-tolylene diisocyanate 14.63 grams and wetting ability chain taking polyethylene glycol-600 (molecular-weight average is 600) 24.00 restrain and are dissolved in respectively in 15.10 grams, 21.95 grams and the positive butyl ester of 24.00 gram solvent acetic acid, fully dissolve, mix.Make the positive butyl acetate solution of hyper-branched polyester-amidoacetic acid, 2,4 toluene diisocyanate n-butyl acetate solution and polyoxyethylene glycol-600 n-butyl acetate solution respectively.The n-butyl acetate solution of 36.58 gram 2,4 toluene diisocyanates is placed the four-hole boiling flask that has stirring, thermometer, dropping funnel and condensing works, under agitation heat up, temperature is: 40 ℃; The n-butyl acetate solution of 48.00 gram polyoxyethylene glycol-600 is placed dropping funnel, slowly splash in the four-hole boiling flask, stir insulation reaction 5 hours; The n-butyl acetate solution that adds 30.20 gram hyperbranched poly ester-acid amides, be warming up to 50 ℃, reacted 5 hours, cooling again, cooling temperature: 10 ℃, be cooling time: 1 hour, rotary evaporation is removed the positive butyl ester of solvent acetic acid, it behind the evaporate to dryness reacting coarse product, (sherwood oil is the mixed solvent of adding 537.30 gram precipitation agents (sherwood oil/deionized water): 80 weight % in crude product, deionized water is: 20 weight %), make graftomer precipitate, use the cup type strainer of A-50 stainless steel (filter opening is of a size of 0.1 μ m) to filter and obtain synthetic product, with 100g/L aqueous ethanolic solution repetitive scrubbing, drying is 24 hours under the vacuum, and vacuum tightness: 0.01Mpa obtains non-ionic hyperbranched macromolecular dispersant.
Accurately weighing 1.00 gram non-ionic hyperbranched macromolecular dispersants add 100 ml deionized water, are configured to the non-ionic hyperbranched macromolecular dispersant aqueous solution of 10g/L; In the non-ionic hyperbranched macromolecular dispersant aqueous solution, add 5.00 gram sodium alkyl naphthalene sulfonates, obtain the combination solution of non-ionic hyperbranched macromolecular dispersant and anionic low-molecular-weight surfactant.
Embodiment five:
The preparation method of non-ionic hyperbranched macromolecular dispersant for organic pigment of the present invention adopts following processing step:
Hydrophobicity hyperbranched polymer of the present invention is got hyper-branched polyester-amine (M
nBeing 16900) 16.90 grams, coupler gets 1,5-naphthalene diisocyanate 3.78 grams and wetting ability chain taking polyethylene glycol monomethyl ether-1000 (molecular-weight average is 1000) 20.00 restrain and are dissolved in respectively in 152.10 grams, 34.02 grams and the 80.00 gram solvent ethyl acetates, fully dissolve, mix.Make hyper-branched polyester-amine ethyl acetate solution, 1 respectively, 5-naphthalene diisocyanate ethyl acetate solution and poly glycol monomethyl ether-500 ethyl acetate solutions.With 37.80 grams 1, the ethyl acetate solution of 5-naphthalene diisocyanate places the four-hole boiling flask that has stirring, thermometer, dropping funnel and condensing works, under agitation heats up, and temperature is: 60 ℃; The ethyl acetate solution of 20.00 gram poly glycol monomethyl ethers-1000 is placed dropping funnel, slowly splash in the four-hole boiling flask, stir insulation reaction 5 hours; The ethyl acetate solution that adds 169.00 gram hyper-branched polyester-amine, be warming up to 50 ℃, reacted 5 hours, cooling again, cooling temperature: 10 ℃, be cooling time: 1 hour, rotary evaporation is removed solvent ethyl acetate, it behind the evaporate to dryness reacting coarse product, (ether is the mixed solvent of adding 460.80 gram precipitation agents (ether/deionized water): 20 weight % in crude product, deionized water is: 80 weight %), make graftomer precipitate, use the cup type strainer of A-50 stainless steel (filter opening is of a size of 0.1 μ m) to filter and obtain synthetic product, with 100g/L aqueous ethanolic solution repetitive scrubbing, drying is 24 hours under the vacuum, and vacuum tightness: 0.01Mpa obtains non-ionic hyperbranched macromolecular dispersant.
Accurately weighing 1.00 gram non-ionic hyperbranched macromolecular dispersants add 100 ml deionized water, are configured to the non-ionic hyperbranched macromolecular dispersant aqueous solution of 10g/L; In the non-ionic hyperbranched macromolecular dispersant aqueous solution, add 5.00 gram dodecyl chloromethyl thioethers, obtain the combination solution of non-ionic hyperbranched macromolecular dispersant and cationic low-molecular-weight surfactant.
Embodiment six:
The preparation method of non-ionic hyperbranched macromolecular dispersant for organic pigment of the present invention adopts following processing step:
Hydrophobicity hyperbranched polymer of the present invention is got aliphatics hyper-branched polyester (M
nBeing 17600) 17.60 grams, coupler gets hexa-methylene 1,6-vulcabond 6.05 gram and wetting ability chain are got polycaprolactone single-acrylate (molecular-weight average is 344) 13.76 grams and are dissolved in 17.60 grams, 9.08 grams and the 13.76 gram solvent methyl n-butyl ketones fully dissolving, mixing respectively.Make aliphatics hyper-branched polyester methyl n-butyl ketone solution, hexa-methylene 1 respectively, 6-vulcabond methyl n-butyl ketone solution and polycaprolactone single-acrylate methyl n-butyl ketone solution.With 15.13 gram hexa-methylenes 1,6-vulcabond methyl n-butyl ketone solution places the four-hole boiling flask that has stirring, thermometer, dropping funnel and condensing works, under agitation heats up, and temperature is: 40 ℃; The methyl n-butyl ketone solution of 27.52 gram polycaprolactone single-acrylates is placed dropping funnel, slowly splash in the four-hole boiling flask, stir insulation reaction 5 hours; The methyl n-butyl ketone solution that adds 35.20 gram aliphatics hyper-branched polyesters, be warming up to 80 ℃, reacted 2 hours, cooling again, cooling temperature: 30 ℃, be cooling time: 2 hours, rotary evaporation removes the methyl n-butyl ketone that desolvates, it behind the evaporate to dryness reacting coarse product, (methyl-phenoxide is the mixed solvent of adding 748.20 gram precipitation agents (methyl-phenoxide/deionized water): 80 weight % in crude product, deionized water is: 20 weight %), make graftomer precipitate, use the cup type strainer of A-50 stainless steel (filter opening is of a size of 0.1 μ m) to filter and obtain synthetic product, with 100g/L methanol aqueous solution repetitive scrubbing, drying is 12 hours under the vacuum, and vacuum tightness: 0.1Mpa obtains non-ionic hyperbranched macromolecular dispersant.
Accurately weighing 1.00 gram non-ionic hyperbranched macromolecular dispersants add 100 ml deionized water, are configured to the non-ionic hyperbranched macromolecular dispersant aqueous solution of 10g/L; In the non-ionic hyperbranched macromolecular dispersant aqueous solution, add 0.20 gram sorbester p17, obtain the combination solution of non-ionic hyperbranched macromolecular dispersant and non-ionic type low-molecular-weight surfactant.
Claims (8)
1. the preparation method of a non-ionic hyperbranched macromolecular dispersant for organic pigment is characterized in that adopting following processing step:
(1), the preparation of hydrophobicity hyperbranched polymer solvent solution, coupler solvent solution and wetting ability chain solvent solution:
Getting the hydrophobicity hyperbranched polymer is: 10～50 weight %, solvent are: 50～90 weight %, and the hydrophobicity hyperbranched polymer is dissolved in the solvent, makes hydrophobicity hyperbranched polymer solvent solution through fully dissolving;
Getting coupler is: 10～40 weight %, solvent are: 60～90 weight %, and coupler is dissolved in the solvent, makes the coupler solvent solution through fully dissolving;
Getting the wetting ability chain is: 20～50 weight %, solvent are: 50～80 weight %, and the wetting ability chain is dissolved in the solvent, makes wetting ability chain solvent solution through fully dissolving;
(2), the coupler solvent solution is placed reaction vessel, under agitation heat up, temperature is: 40 ℃～60 ℃, add wetting ability chain solvent solution and place above-mentioned reaction vessel, through stirring, after the insulation reaction 1～5 hour, add hydrophobicity hyperbranched polymer solvent solution, under agitation heat up, temperature is: 50 ℃～80 ℃, insulation reaction 2～5 hours, through cooling, cooling temperature: 10 ℃～30 ℃, be cooling time: 1～2 hour again, rotary evaporation removes and desolvates, be reacting coarse product behind the evaporate to dryness, add the mixing solutions of precipitation agent and deionized water then, after filtration, washing, vacuum-drying 12～24 hours was non-ionic hyperbranched macromolecular dispersant, and vacuum tightness is: 0.01Mpa～0.1Mpa.
2. the preparation method of a kind of non-ionic hyperbranched macromolecular dispersant for organic pigment according to claim 1 is characterized in that described hydrophobicity hyperbranched polymer is a kind of in aromatic series hyper-branched polyester, aliphatics hyper-branched polyester, hyperbranched poly ester-acid amide, hyper-branched polyester-amine, hyper-branched polyester-imide, hyperbranched polyether, hyperbranched polyether ketone, hyperbranched polyether imide, hyperbranched polyphenyl, hyperbranched polyamine, ultrabranching polyamide, hyperbranched polyureas, hyperbranched poly silica silane or the hyperbranched Polycarbosilane.
3. the preparation method of a kind of non-ionic hyperbranched macromolecular dispersant for organic pigment according to claim 1, it is characterized in that described wetting ability chain is a polyoxyethylene glycol-600, polyoxyethylene glycol-800, polyoxyethylene glycol-1000, polyoxyethylene glycol-2000, polyoxyethylene glycol-4000, poly glycol monomethyl ether-500, poly glycol monomethyl ether-750, poly glycol monomethyl ether-1000, poly glycol monomethyl ether-2500, poly glycol monomethyl ether-5000, polyvinyl acetal, polycaprolactone single-acrylate, trolamine, tri-isopropanolamine, diisopropanolamine (DIPA), N, the N-dimethyl propanol amine, one or both mixtures in the 2 hydroxy propanoic acid.
4. the preparation method of a kind of non-ionic hyperbranched macromolecular dispersant for organic pigment according to claim 1, it is characterized in that described coupler is 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,4-ethylbenzene vulcabond, 4,4 '-diphenylmethanediisocyanate, 1,5-naphthalene diisocyanate, hexa-methylene 1,6-vulcabond, 4, a kind of or two kinds of mixtures in 4 '-dicyclohexyl methane diisocyanate.
5. the preparation method of a kind of non-ionic hyperbranched macromolecular dispersant for organic pigment according to claim 1 is characterized in that described solvent is one or more mixed solvents in ethyl acetate, n-butyl acetate, methylene dichloride, chloroform, tetracol phenixin, acetone, butanone, methyl n-butyl ketone, pyrrolidone, methyl-2-pyrrolidone, dimethyl pyrrolidone, dimethyl sulfoxide (DMSO), dimethyl formamide, TriMethylolPropane(TMP), the tetrahydrofuran (THF).
6. the preparation method of a kind of non-ionic hyperbranched macromolecular dispersant for organic pigment according to claim 1 is characterized in that described precipitation agent is one or more mixtures in methyl alcohol, ethanol, propyl alcohol, Virahol, propyl carbinol, propyl carbinol, isopropylcarbinol, water, ether, dipropyl ether, methyl-phenoxide, hexanaphthene, methylcyclohexane, sherwood oil, benzene,toluene,xylene, the ethylbenzene.
7. the preparation method of a kind of non-ionic hyperbranched macromolecular dispersant for organic pigment according to claim 1, the mol ratio that it is characterized in that described coupler and wetting ability chain is 2.1～0.9: 1; The mol ratio of hydrophobicity hyperbranched polymer and wetting ability chain is 1: 20～40.
8. the preparation method of a kind of non-ionic hyperbranched macromolecular dispersant for organic pigment according to claim 1, the mass ratio that it is characterized in that described precipitation agent and deionized water is 1: 4～4: 1, and the mixing solutions consumption of precipitation agent and deionized water is 10～20 times of reacting coarse product total mass.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6472463B1 (en) * | 1999-12-17 | 2002-10-29 | E. I. Du Pont De Nemours And Company | Graft copolymer pigment dispersant |
| CN1456598A (en) * | 2003-05-29 | 2003-11-19 | 上海交通大学 | Organic pigments with superbranched polymers as cores and preparations thereof |
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