WO2007135935A1 - 分散剤 - Google Patents
分散剤 Download PDFInfo
- Publication number
- WO2007135935A1 WO2007135935A1 PCT/JP2007/060093 JP2007060093W WO2007135935A1 WO 2007135935 A1 WO2007135935 A1 WO 2007135935A1 JP 2007060093 W JP2007060093 W JP 2007060093W WO 2007135935 A1 WO2007135935 A1 WO 2007135935A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- water
- acid
- soluble polymer
- polymer
- component
- Prior art date
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- 239000002270 dispersing agent Substances 0.000 title claims abstract description 55
- 239000000178 monomer Substances 0.000 claims abstract description 39
- -1 alkali metal salt Chemical class 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 229920003169 water-soluble polymer Polymers 0.000 claims abstract description 30
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 27
- 229920000570 polyether Polymers 0.000 claims abstract description 27
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 14
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims abstract description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims abstract 2
- 239000007864 aqueous solution Substances 0.000 claims description 28
- 229920001451 polypropylene glycol Polymers 0.000 claims description 23
- 229920001223 polyethylene glycol Polymers 0.000 claims description 17
- 239000002202 Polyethylene glycol Substances 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 5
- 239000000470 constituent Substances 0.000 claims description 3
- 239000000049 pigment Substances 0.000 abstract description 27
- 239000002002 slurry Substances 0.000 abstract description 15
- 239000006185 dispersion Substances 0.000 abstract description 14
- 230000007774 longterm Effects 0.000 abstract description 2
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 42
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 20
- 238000000034 method Methods 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 17
- 239000002253 acid Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 14
- 239000003599 detergent Substances 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 11
- 238000010298 pulverizing process Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 229910000019 calcium carbonate Inorganic materials 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910019142 PO4 Inorganic materials 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 239000001023 inorganic pigment Substances 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
- 239000010452 phosphate Substances 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 150000001991 dicarboxylic acids Chemical class 0.000 description 7
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 7
- 239000011499 joint compound Substances 0.000 description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
- 150000002978 peroxides Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 239000011976 maleic acid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000004568 cement Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
- JCLCXMQLXFRIPW-UHFFFAOYSA-N 3-[1-[1-(1-hydroxypropan-2-yloxy)propan-2-yloxy]propan-2-yloxy]propane-1,2-diol Chemical compound OCC(C)OCC(C)OCC(C)OCC(O)CO JCLCXMQLXFRIPW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000005553 drilling Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 3
- 230000002123 temporal effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 238000001238 wet grinding Methods 0.000 description 3
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical compound CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 2
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- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 238000010559 graft polymerization reaction Methods 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
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- 229920002959 polymer blend Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012966 redox initiator Substances 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
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- 229910052708 sodium Inorganic materials 0.000 description 2
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- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
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- 239000000126 substance Substances 0.000 description 2
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- 230000008719 thickening Effects 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- MYOQALXKVOJACM-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy pentaneperoxoate Chemical compound CCCCC(=O)OOOC(C)(C)C MYOQALXKVOJACM-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- BNXZHVUCNYMNOS-UHFFFAOYSA-N 1-butylpyrrolidin-2-one Chemical compound CCCCN1CCCC1=O BNXZHVUCNYMNOS-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- NARVIWMVBMUEOG-UHFFFAOYSA-N 2-Hydroxy-propylene Natural products CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
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- 239000000600 sorbitol Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 239000001040 synthetic pigment Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JIYXDFNAPHIAFH-UHFFFAOYSA-N tert-butyl 3-tert-butylperoxycarbonylbenzoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC(C(=O)OC(C)(C)C)=C1 JIYXDFNAPHIAFH-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/24—Macromolecular compounds
- C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C04B24/2641—Polyacrylates; Polymethacrylates
- C04B24/2647—Polyacrylates; Polymethacrylates containing polyether side chains
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B28/00—Compositions of mortars, concrete or artificial stone, containing inorganic binders or the reaction product of an inorganic and an organic binder, e.g. polycarboxylate cements
- C04B28/02—Compositions of mortars, concrete or artificial stone, containing inorganic binders or the reaction product of an inorganic and an organic binder, e.g. polycarboxylate cements containing hydraulic cements other than calcium sulfates
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- 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
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
- C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/002—Pigment pastes, e.g. for mixing in paints in organic medium
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/45—Anti-settling agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
Definitions
- the present invention relates to a dispersant having excellent dispersibility and storage stability.
- polymers obtained by graft polymerization of an ethylenically unsaturated carboxylic acid to polyalkylene glycol are well known, and include detergent builders, metal corrosion inhibitors, soil water reducers, and electronic component cleaners. , Deinking agents, bleaching aids, film formation inhibitors, sequestering agents, and many other fields.
- Patent Documents 1 and 2 etc. cement dispersants
- Patent Document 3 cement dispersants, bubble formers, coagulation retarders and retention agents have also been reported.
- a dispersant such as a nonionic (non-ionic) polymer
- Patent Documents 4 to 6 examples of applying a polymer mixture to a pigment dispersant for papermaking
- Patent Document 7 an example of applying a polymer mixture to a dispersant as a biodegradable polymer
- the designs of polyether compounds and ethylenically unsaturated rubonic acids used in these water-soluble polymers differ depending on the application, and are not always satisfactory depending on the application.
- Patent Document 1 Japanese Patent Laid-Open No. 10-236859 (Claims)
- Patent Document 2 Japanese Patent Laid-Open No. 2003-12358 (Claims)
- Patent Document 3 Japanese Patent Laid-Open No. 6-211949 (Claims)
- Patent Document 4 Japanese Patent Laid-Open No. 10-204320 (Claims)
- Patent Document 5 Japanese Unexamined Patent Application Publication No. 2004-76164 (Claims)
- Patent Document 6 Japanese Patent Laid-Open No. 2005-220492 (Claims)
- Patent Document 7 Japanese Patent Laid-Open No. 3-177406 (Claims)
- an object of the present invention is to provide a pigment slurry having a stable viscosity characteristic due to excellent dispersibility of dispersoids such as pigments and a large dispersion stability effect.
- a novel dispersant more specifically, it is excellent in dispersibility even at a high concentration of dispersoid and can be made to have a low viscosity.For example, for wet grinding of heavy calcium carbonate, it generates heat during grinding.
- An object of the present invention is to provide a dispersant containing a water-soluble polymer that can be suppressed, has excellent temporal stability, and has good redispersibility.
- the present invention comprises (A) an ethylenically unsaturated monocarboxylic acid monomer or anhydride thereof, or an ethylenically unsaturated dicarboxylic acid monomer or anhydride thereof, and (B) a polyether compound as essential components.
- the ratio of the number of moles of alkylene oxide added in the component (B) to the number of moles of carboxyl groups in the component (A) [(B) / (A)] is 0.6 or less
- acrylic acid or methacrylic acid is referred to as (meth) acrylic acid
- acrylate or methacrylate is referred to as (meth) acrylate.
- the dispersant containing the water-soluble polymer of the present invention has good dispersion characteristics in an aqueous medium as a pigment slurry having a pigment as a dispersoid.
- pigment aggregation and thickening are not observed over a long period of time, and the slurry is excellent in stability over time, and is useful for wet pulverization to obtain an inorganic pigment dispersant, particularly a calcium carbonate slurry for papermaking.
- the dispersant of the present invention comprises (A) an ethylenically unsaturated monocarboxylic acid monomer or an anhydride thereof, or an ethylenically unsaturated dicarboxylic acid monomer or an anhydride thereof, and (B) a polyester compound.
- the ratio of the number of moles of alkylene oxide added in component (B) to the number of moles of carboxyl groups in component (A) [(B) / (A)] is 0.6 or less, and the total amount of component (B) Less than 25% by weight of the water-soluble polymer, and the alkali metal salt or ammonium salt of Z or its water-soluble polymer. This will be explained in detail below.
- the component (A) constituting the water-soluble polymer of the present invention is an ethylenically unsaturated monocarboxylic acid monomer or an anhydride thereof, or an ethylenically unsaturated dicarboxylic acid monomer or an anhydride thereof.
- the ethylenically unsaturated monocarboxylic acid monomer of the present invention is an ethylenically unsaturated monocarboxylic acid, an alkali metal salt thereof and an ammonium salt.
- Specific examples include (meth) attalic acid, crotonic acid, bulacetic acid, and acryloxypropionic acid. Of these, (meth) acrylic acid is preferred and is an ethylenically unsaturated monocarboxylic acid monomer.
- Ethylenically unsaturated dicarboxylic acid monomers include ethylenically unsaturated dicarboxylic acids, their alkali metal salts, ammonium salts, and anhydrides of cis-dicarboxylic acids.
- maleic acid examples include maleic acid, maleic anhydride, itaconic acid, mesaconic acid, fumaric acid, and citraconic acid.
- maleic acid, maleic anhydride and itaconic acid are preferred ethylenically unsaturated dicarboxylic acid monomers.
- Component (A) useful in the present invention is the above-mentioned acid, an alkali metal salt or an ammonium salt thereof.
- Suitable bases for neutralizing the monomeric acid in component (A) include inorganic alkali agents such as alkali metal hydroxides such as ammonia, potassium hydroxide, and sodium hydroxide. And organic amines such as jetanolamine and triethanolamine. Power of component (A) Do not neutralize before polymerizing the rubonic acid monomer, or neutralize to 0-60%, and when water is added during polymerization or after polymerization, 50-: LOO%, preferably 50 ⁇ : Neutralize to LOO% The
- the (B) polyether compound forming the polymer of the present invention is water-soluble or alcohol-soluble, has an alkylene oxide unit, and is sufficiently extracted by radicals derived from a peroxide-based initiator. It is a compound containing a hydrogen atom.
- the alkylene group may be completely linear, such as polyethylene glycol, or branched, such as polypropylene glycol.
- polyethylene glycol polypropylene glycol, polybutylene glycol, polyethylene triol and polypropylene triol or copolymers thereof.
- the polyalkyleneoxides may be etherified with aliphatic or araliphatic at the chain ends, in which case the corresponding aliphatic groups consist of 1 to 18 carbon atoms.
- the aliphatic group may further have a functional group such as a hydroxyl group, a sulfonyl group, an amino group or a carboxyl group.
- the polyether compound can also be obtained by polymerizing an alkylene oxide by a known method using water or alcohol as a starting point.
- alcohols for obtaining the polyether compound include primary alcohols having 1 to 4 carbon atoms such as methanol, ethanol, n-propanol, and n-butanol, secondary alcohols having 3 to 5 carbon atoms, and ethylene glycol.
- Diols such as diethylene glycol, propanediol, butanediol, and propylene glycol, triols such as glycerin and trimethylolpropane, polyols such as sorbitol, aromatic alcohols such as phenol, alkylphenol, and naphthol.
- the cyclic ether include ethylene oxide, propylene oxide, isobutylene oxide and the like.
- the terminal hydroxyl group of the polyether compound obtained as described above is substituted with a fatty acid having 2 to 6 carbon atoms, for example, succinic acid, succinic anhydride, maleic acid. It is possible to use those esterified with a dicarboxylic acid such as maleic anhydride or fumaric acid.
- the ratio [(B) / (A)] of the number of moles of alkylene oxide added in the component (B) to the number of moles of the carboxyl group in the component (A) is 0.6. It is as follows. In polymer When the molar ratio of the alkylene oxide group to the carboxyl group exceeds 0.6, the adsorptive power of the resulting polymer to the pigment decreases, and as a result, the temporal stability and redispersibility of the dispersed slurry are poor. It is not preferable.
- the content of the (B) polyether compound in the polymer is less than 25% by weight, more preferably less than 20% by weight, based on the total weight of all the monomers constituting the polymer. If the content is 25% by weight or more, the dispersion may have poor stability over time and water solubility may not be maintained.
- the polyether compound is soluble in water or alcohol at an arbitrary ratio near room temperature.
- component (A) (1) after graft polymerization using an alcoholic acid peroxide initiator that is soluble in alcohol, the alcohol solvent is removed, neutralized, and water-solubilized. And (2) polymerization using water-soluble peroxide-based initiators in water at 80 ° C or higher. Since method (2) can be carried out at a lower cost than method (1), it is desirable that the cloud point of a 1% aqueous solution of a polyether compound be 80 ° C or higher in order to proceed polymerization in a homogeneous system. Better! /.
- the molecular weight of these polyether compounds is 100 to 10000, preferably 100 to 300, and more preferably 100 to 1800.
- the molecular weight is less than 100, the graft ratio is lowered and the wettability of the obtained water-soluble polymer to the pigment is lowered.
- the molecular weight exceeds 10,000, the initial dispersibility of the pigment may decrease.
- the alkylene oxide is preferably a compound having an alkylene oxide unit having 3 to 4 carbon atoms, and in particular, a propylene oxide unit is essential. Those are preferred.
- a copolymer obtained by copolymerizing ethylene oxide as an alkylene oxide copolymerizable with an alkylene oxide having 3 to 4 carbon atoms is also included.
- the polyether compound has an essential propylene oxide unit, (bl) a polypropylene oxide having a molecular weight of 700 or less, or a derivative thereof, or (b2) a polyethylene dialicol in a total constituent amount of the compound. It is desirable to contain at least one of polyethylene glycol and polypropylene glycol copolymer containing 60% by weight or more of the above.
- the molecular weight is 100 to 700 (caroten with propylene glycol). It is more desirable that the molecular weight is about 100 to 400 (n: about 2 to 6).
- (bl) include dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethanolate ether, dipropylene glycol monomonopropylene ether, tripropylene glycol, tripropylene glycol monomono.
- the polyether compound is (b2), wherein the polyethylene glycol polypropylene glycol copolymer polyethylene glycol 60 wt 0/0 or more of the total configuration weight 3000 or less molecular weight in gesture et desirable 5,000 It is desirable that
- (b2) include polyethylene glycol polypropylene glycol having a molecular weight of 545 (ethylene oxide content 67 wt%), polyethylene glycol polypropylene glycol having a molecular weight of 1040 (ethylene oxide content 60 wt%), and polyethylene having a molecular weight of 1400.
- Glycol Polypropylene glycol ethylene oxide content 60 wt%)
- molecular weight 1970 polyethylene glycol Polypropylene glycol
- polyethery compound may be used alone or in combination of two or more.
- the water-soluble polymer of the present invention comprises the components (A) and (B) as essential components.
- iS Other monomers can be used as a constituent component within the range not impairing the function of the polymer of the present invention (preferably 10% by weight or less of the total monomer weight).
- Other monomers include alkyl (meth) acrylates, hydroxy (meth) acrylates, (meth) acrylamide, butyl acetate, N-butyl pyrrolidone, (meth) atalyloyl morpholine, (meth) ) Acrylonitrile, (meth) acrylamide alkylalkanesulfonic acids, sulfonic acid-containing vinyl monomers, phosphoric acid group-containing vinyl monomers, phosphoric ester group-containing vinyl monomers, and the like.
- a crosslinkable monomer such as maleic acid diaryl ester, polyallyl saccharose and the like may be contained.
- alkyl (meth) acrylates include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, (meth) acrylic acid. 2-Ethylhexyl, cyclohexyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, and the like.
- (meth) acrylamide alkylalkanesulfonic acids include 2-acrylamido-2-methylpropanesulfonic acid, acrylamide methanesulfonic acid, acrylamide ethanesulfonic acid, acrylamide butanesulfonic acid, and the like.
- the sulfonic acid-containing monomer examples include (meth) aryl sulfonic acid, styrene sulfonic acid, a-methylol styrene sulphonic acid, isoprene sulphonic acid, vinylo retono renos sulphonic acid, (meth) allyl.
- Oxybenzene sulfonic acid, (meth) aryloxy 2-hydroxypropylene Examples include sulfonic acid, (meth) acrylic acid 3-sulfopropyl, and itaconic acid bis (3-sulfopropyl).
- phosphoric acid group-containing butyl monomer examples include mono (2-hydroxyethyl acrylate) acid phosphate, mono (2-hydroxy ethynole methacrylate) acid phosphate, and mono (2-hydroxypropyl acrylate).
- the phosphoric acid ester group-containing bulu monomer examples include diphenol-two-allyloyl oxetyl phosphate, diphenol-two-methacryloyl oxychetyl phosphate, dimethyl 2-methacryloyl oxychetyl phosphate, and jetyl.
- Examples include 2-methacryloyloxetyl phosphate, dipropyl 2-methacryloyloxetyl phosphate, and the like.
- a method for producing the water-soluble polymer of the present invention there are known a solution polymerization method, an aqueous solution polymerization method, an ion polymerization method, a high-temperature high-pressure polymerization method, a suspension polymerization method, etc., but the water-soluble polymer of the present invention is synthesized.
- a solution polymerization method, an aqueous solution polymerization method, and a high-temperature and high-pressure polymerization method at 160 ° C. or lower are preferred from the standpoint of ease of polymerization operation and easy adjustment of the degree of polymerization.
- the synthesis of the water-soluble polymer of the present invention is more preferably an aqueous solution polymerization method in which a method using a radical polymerization initiator is preferred because the polymerization operation and molecular weight adjustment are easy and can be produced at low cost.
- the polymer of the present invention comprises (A) an ethylenically unsaturated monocarboxylic acid monomer or an anhydride thereof, or an ethylenically unsaturated dicarboxylic acid monomer or an anhydride thereof, and (B) a polyester compound. Or (C) other monomer-powered mixed liquids in the presence of a radical polymerization initiator, and preferably (A), (B) and (C) components.
- the main component is a strong graft polymer.
- a radical polymerization initiator is generally used.
- Peroxyacid-based initiators can be used. Specifically, water-soluble sodium persulfate, potassium persulfate, persulfates such as ammonium persulfate, t-butylnodide peroxide, cumene hydride peroxide, diisopropylbenzene hydride peroxide
- ketone baroxides such as oil-soluble methyl ethyl ketone peroxide, cyclohexanone peroxide, di-t-butyl peroxide, t-butyl tamil peroxide, dicumyl peroxide, ⁇ , bis (T-butylperoxy) ⁇ Diisopropylbenzene, ⁇ , ⁇ '-bis (t-butylperoxy) ⁇ Dialkyl peroxides such as diisopropylhexyne; t-butylperoxyacetate, t-butylperoxylaurate, t-butylperoxyla Peroxyesters such as benzoate, di-t-butylperoxyisophthalate, 2,5 dimethyl-2,5 di (benzoylperoxy) hexane, t-butylperoxyisopropyl carbonate; n-butyl-4,4 bis (T-butylperoxy) valerate,
- peracids such as hydrogen peroxide and persulfates, which have low molecular weight control and low decomposition temperature, are preferred. These may be used alone or in combination of two or more.
- the amount of the polymerization initiator is not particularly limited, but is preferably 0.1 to 15% by weight, more preferably 0.5 to 10% by weight based on the total amount of monomers. If it is less than this, the grafting efficiency of the monomer onto the polyether will decrease. If it is more than this, it will remain after the polymerization, and it is not good because it may impair the stability of the polymer or adversely affect the dispersibility.
- the polymerization initiator can be added to the polyether in advance, and can be added simultaneously with the monomer to be added.
- a water-soluble redox initiator may be used.
- This initiator includes sodium bisulphite, sodium sulfite, i.e. which can be used together with a suitable oxidizing agent such as the above-mentioned polymerization initiator.
- suitable oxidizing agent such as the above-mentioned polymerization initiator.
- reducing agents such as soascorbic acid, sodium formaldehyde monosulfoxylate, sodium, and idrosulfite sodium, and iron myoban and potassium myoban.
- the redox initiator is used in an amount of 0.05 to 8%, based on the weight of the total monomer. A preferred range is 0.5-5% by weight of the total monomer. Many of these initiators introduce salt by-products into the polymer product. When used, it is preferable to minimize the amount of these initiators used.
- chain transfer agents such as mercaptoacetic acid, mercaptopropionic acid, 2-propanethiol, 2-mercaptoethanol, thiophenol, dodecyl mercaptan, thioglycerol, etc. Add an appropriate amount of to the polymerization system.
- water is preferably used alone as the solvent, preferably in the case of using the aqueous solution polymerization method usually carried out using a polymerization initiator in a solvent. Accordingly, a hydrophilic organic solvent may be appropriately added to water.
- a hydrophilic organic solvent may be appropriately added to water.
- lower alcohols such as methanol, ethanol and 2-propanol
- amides such as dimethylformamide
- ketones such as acetone
- ethers such as 1,4-dioxane, etc.
- the addition ratio of the hydrophilic organic solvent is preferably 20% by weight or less based on the total amount of the mixed solvent with water. If it exceeds 20% by weight, the resulting copolymer may be separated and Z or precipitated.
- an alcohol particularly one having a low boiling point of 1 to 4 carbon atoms that can be easily removed later.
- Specific examples include methanol, ethanol, isopropanol, n-propanol, n-butanol, sec-butanol, tert-butanol and the like.
- the preferred polymerization temperature during the polymerization reaction is 50 to 150 ° C, more preferably 60 to 100 ° C. When the temperature is lower than 50 ° C, the grafting efficiency of the monomer onto the polyether decreases. In addition, at temperatures higher than 150 ° C !, thermal decomposition of the polyether and the resulting copolymer may occur.
- the preferred polymerization time is 3 to 25 hours.
- the polymer of the present invention has an appropriate dispersibility and an appropriate weight average molecular weight (Mw) of 1,000-100,000 by gel permeation chromatography (GPC) using polystyrene as a reference substance. The range of 1,000-30,000 is more preferable in that a high solution viscosity can be obtained.
- the polymer has an Mw of less than 1,000, a sufficient dispersing effect cannot be obtained. If the polymer has an Mw of more than 30 000, the viscosity increases and becomes insoluble or forms a massive substance. It will not work.
- the number average molecular weight (Mn) is more preferably in the range of 1,000 to 5,000 in terms of obtaining an appropriate dispersibility and an appropriate solution viscosity that are preferably from 500 to 15,000. A polymer having an Mn of less than 500 cannot provide a sufficient dispersing effect, and if the Mn exceeds 15,000, the viscosity increases and becomes insoluble or forms a massive substance and does not function as a dispersant. .
- the water-soluble polymer of the present invention can be obtained as an aqueous solution or a solution depending on the production method or the type of post-treatment. If an organic solvent is included, remove the solvent by distillation, vacuum distillation, drying, etc., and then neutralize with an alkali to make it water soluble.
- the dispersant of the present invention can be used by dissolving the water-soluble polymer obtained as described above alone in a solvent such as water or alcohol. It can also be used.
- a solvent such as water or alcohol.
- the base include alkali metal salts such as sodium salt and potassium salt, alkaline earth metal salts such as calcium salt, trivalent metal salts such as aluminum salt, ammonium salt, monoethanolamine, and triethanolamine. Mention may be made of organic amine salts such as min.
- other emulsion emulsions, viscosity modifiers, fragrances, antioxidants, UV absorbers, bactericides, preservatives, and the like can be blended. Water is preferred as a solvent for blending these.
- the dispersant of the present invention can be used for various applications.
- a dispersant for ceramic particles a dispersant for agricultural chemical granules, a dispersant for mud, a dispersant for cement, a dispersant for scale dispersion, and a detergent builder
- examples thereof include a dispersant, a dispersant for inorganic pigments, and a dispersant for organic pigments.
- inorganic pigment dispersants particularly those useful for wet grinding in the papermaking process, are useful.
- specific examples of each use are as follows. Insecticides for ceramic manufacturing processes such as ferrite, alumina, zirconium, barium titanate, silicon carbide, cordierite, aluminum hydroxide, etc. And agrochemical grain dispersants such as fungicides, herbicides and acaricides.
- dispersant for drilling mud for sewage sludge cake and water purification sludge cake, for cement, mortar dispersant and concrete dispersant, for scale dispersion, calcium carbonate, calcium phosphate and
- scale dispersants such as silica and detergent builders include detergent addition agents such as detergents for clothes, detergents for clothes, liquid detergents for dishes, detergents for detergents such as bleaching powder detergents and bleaching liquid detergents.
- inorganic pigments include calcium carbonate wet pulverization, light calcium carbonate production process, recycled sludge, and caustic light calcium carbonate production process dispersants
- organic pigments include water-based inks. Examples thereof include a dispersant for pigment.
- examples of inorganic pigments include body pigments such as My strength, talc, kaolin, calcium carbonate, anhydrous silicic acid, aluminum oxide, barium sulfate, etc .; Bengala , Yellow iron oxide, black iron oxide, chromium oxide, ultramarine pigment, bitumen, carbon black, etc .; white pigments such as titanium dioxide and zinc oxide; pearlescent pigments such as mica titanium, fish phosphorus foil, bismuth oxychloride; nitriding
- organic synthetic pigments include dyes, lakes, organic pigments, etc.
- natural pigments include ⁇ -carotene, Carsamine and the like can be mentioned, and one or more of them can be selected.
- dispersant for blending cement milk and clay is used as a dispersant for soil improvement.
- clay various kinds such as mud, bentonite and kaolin produced in excavation work can be used.
- the dispersant of the present invention is also very useful as a bentonite dispersant for drilling mud.
- % and part mean “% by weight” and “part by weight”, respectively.
- an initiator aqueous solution prepared by mixing sodium persulfate 1. Og and 2.4 g of deionized water was supplied all at once, and the power was maintained at the same temperature for 30 minutes to complete the polymerization. Thereafter, the polymer was taken out after cooling to 60 ° C.
- an aqueous solution of polymer El having a solid content concentration of 27.5%, a weight average molecular weight (Mw) of 6200, and a number average molecular weight (Mn) of 2500 was obtained.
- Example 3 (Production of polymer ⁇ 3)
- a separable flask was charged with 5 lg (10% equivalent) of maleic acid, (1) Acrylic acid amount was changed to 4 08 g (80% equivalent), and (3) 48% NaOH aqueous solution was changed to 455.5 g.
- an aqueous solution of polymer E3 having a solid concentration of 27.4% and Mw5500 and Mn2500 was obtained.
- Example 6 (Production of polymer ⁇ 6)
- Example 2 The same procedure as in Example 1 was conducted except that the polyether compound was not used, (1) the amount of acrylic acid was changed to 510. Og (equivalent to 100%), and (3) the 48% NaOH aqueous solution was changed to 528.2 g. An aqueous solution of polymer C1 having a solid content concentration of 27.4%, Mw5500, and Mn2800 was obtained.
- Polypropylene glycol 255 g (50 mass 0/0 equivalent) in a separable flask (propylene glycol addition molar number 4, molecular weight 250), (1) the amount of acrylic acid in 255 g (50% equivalent), (3) 48% An aqueous solution of polymer C3 having a solid content concentration of 27.4% and Mw5600, Mn2600 was obtained in the same manner as in Example 1 except that the NaOH aqueous solution was changed to 264. lg.
- the molecular weights of the polymers E1 to E7 and C1 to C3 were measured by aqueous GPC using 0.1M NaCl and 0.1M phosphate buffer as eluent. The average molecular weight was calculated by preparing a calibration curve using polyacrylic acid as a reference substance.
- Dispersing machine Sand grinder (Igarashi Machine)
- Inorganic pigment Heavy calcium carbonate
- Dispersant addition amount 0.7% in rosin solid content relative to pigment solid content
- Dispersion medium distilled water
- the temperature of the dispersed slurry was measured with a thermometer, and then filtered with a 100 mesh filter cloth.
- the solid content concentration of the pigment slurry obtained by pulverization as in b) above is adjusted by diluting to 75% with distilled water, and kept at 25 ° C, and immediately after dispersion, after 1 day of dispersion, after dispersion 7
- the B-type viscosity (25 ° C, 6rpm, # 2 or # 3 rotor) after days was measured. Those that did not thicken over time were considered to have high stability over time.
- PPG Polypropylene glycol (nl: Number of moles of propylene oxide with average)
- PEG Polyethylene glycol (n2: Number of moles of ethylene oxide with average)
- PPM Polypropylene glycol monomethyl ether
- TPGG Tripropylene glycol glyceryl ether
- the polymer of the example had better dispersion characteristics than the polymer of the comparative example. That is, in addition to the fluidity and dispersibility during wet pulverization of heavy calcium carbonate, which is an inorganic pigment, the temporal stability of the pigment slurry was excellent.
- the dispersant containing the water-soluble polymer of the present invention has good dispersion characteristics in an aqueous medium. That is, heat generation during pulverization can be suppressed even with a low addition amount, and a pigment slurry having a low particle diameter can be obtained. In addition, there is no aggregation or thickening of the pigment over a long period of time, and the dispersion slurry is excellent in stability over time. Thus, it is useful for inorganic pigment dispersants, especially wet milling applications in the papermaking process.
- the dispersant of the present invention can be expected to have practical long-term stability as a mud drilling mud dispersant, a mortar dispersant, a scale dispersant, a detergent builder dispersant, and a ceramic particle dispersant. .
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Ceramic Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Structural Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Graft Or Block Polymers (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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EP07743528A EP2025394A1 (en) | 2006-05-22 | 2007-05-17 | Dispersing agent |
JP2008516632A JP5105094B2 (ja) | 2006-05-22 | 2007-05-17 | 分散剤 |
US12/299,822 US20090176925A1 (en) | 2006-05-22 | 2007-05-17 | Dispersing agent |
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JP2006141049 | 2006-05-22 | ||
JP2006-141049 | 2006-05-22 |
Publications (1)
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WO2007135935A1 true WO2007135935A1 (ja) | 2007-11-29 |
Family
ID=38723247
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PCT/JP2007/060093 WO2007135935A1 (ja) | 2006-05-22 | 2007-05-17 | 分散剤 |
Country Status (6)
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US (1) | US20090176925A1 (ja) |
EP (1) | EP2025394A1 (ja) |
JP (1) | JP5105094B2 (ja) |
KR (1) | KR20090018643A (ja) |
CN (1) | CN101454073A (ja) |
WO (1) | WO2007135935A1 (ja) |
Cited By (2)
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WO2010143554A1 (ja) * | 2009-06-11 | 2010-12-16 | 東亞合成株式会社 | 顔料用分散剤及びその用途 |
CN105542100A (zh) * | 2015-12-10 | 2016-05-04 | 北京正富混凝土有限责任公司 | 一种高性能减水剂及其制备方法 |
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DE102010001891A1 (de) | 2010-02-12 | 2011-08-18 | Leibniz-Institut für Polymerforschung Dresden e.V., 01069 | Dispergiermittel zur Stabilisierung von Dispersionen |
EP2644578A1 (en) * | 2012-03-30 | 2013-10-02 | Technische Universität München | Copolymer for dispersant for cement, dispersant for cement, and cement composition |
JP5755717B2 (ja) | 2013-03-08 | 2015-07-29 | 楠本化成株式会社 | 無機微粒子高濃度分散体用粘性調整剤及びそれが配合された無機微粒子高濃度分散体 |
US9546110B2 (en) | 2015-06-15 | 2017-01-17 | Gcp Applied Technologies Inc. | Superplasticizing admixture for cementitious compositions |
US9624130B2 (en) * | 2015-06-15 | 2017-04-18 | Gcp Applied Technologies Inc. | Optimizing polycarboxylate admixtures for cementitious compositions |
JP2021526453A (ja) * | 2018-06-01 | 2021-10-07 | ダウ グローバル テクノロジーズ エルエルシー | 酸グラフトeo−poコポリマーを使用した、シリカスケール阻害の方法 |
CN111116837B (zh) * | 2019-12-30 | 2022-09-30 | 上海东升新材料有限公司 | 一种具有辅助增白效果的高效重钙研磨分散剂及其制备方法 |
CN116515055B (zh) * | 2023-05-11 | 2024-04-05 | 宇昂科技有限公司 | 一种水溶性聚合物分散剂及其制备方法和应用 |
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- 2007-05-17 US US12/299,822 patent/US20090176925A1/en not_active Abandoned
- 2007-05-17 CN CNA2007800190165A patent/CN101454073A/zh active Pending
- 2007-05-17 KR KR1020087030606A patent/KR20090018643A/ko not_active Application Discontinuation
- 2007-05-17 WO PCT/JP2007/060093 patent/WO2007135935A1/ja active Application Filing
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JP5776549B2 (ja) * | 2009-06-11 | 2015-09-09 | 東亞合成株式会社 | 顔料用分散剤及びその用途 |
CN105542100A (zh) * | 2015-12-10 | 2016-05-04 | 北京正富混凝土有限责任公司 | 一种高性能减水剂及其制备方法 |
CN105542100B (zh) * | 2015-12-10 | 2017-10-20 | 北京正富混凝土有限责任公司 | 一种高性能减水剂及其制备方法 |
Also Published As
Publication number | Publication date |
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EP2025394A1 (en) | 2009-02-18 |
US20090176925A1 (en) | 2009-07-09 |
CN101454073A (zh) | 2009-06-10 |
JPWO2007135935A1 (ja) | 2009-10-01 |
KR20090018643A (ko) | 2009-02-20 |
JP5105094B2 (ja) | 2012-12-19 |
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