JP6122251B2 - Method for producing organic compound-coated powder - Google Patents
Method for producing organic compound-coated powder Download PDFInfo
- Publication number
- JP6122251B2 JP6122251B2 JP2012091199A JP2012091199A JP6122251B2 JP 6122251 B2 JP6122251 B2 JP 6122251B2 JP 2012091199 A JP2012091199 A JP 2012091199A JP 2012091199 A JP2012091199 A JP 2012091199A JP 6122251 B2 JP6122251 B2 JP 6122251B2
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- JP
- Japan
- Prior art keywords
- acid
- powder
- organic compound
- compound
- organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000843 powder Substances 0.000 title claims description 70
- 150000002894 organic compounds Chemical class 0.000 title claims description 43
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- -1 aluminum compound Chemical class 0.000 claims description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000010438 heat treatment Methods 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 12
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 8
- 238000010298 pulverizing process Methods 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 7
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 claims description 6
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 3
- 150000003609 titanium compounds Chemical class 0.000 claims description 2
- 150000003755 zirconium compounds Chemical class 0.000 claims description 2
- 150000003377 silicon compounds Chemical class 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 33
- 239000000194 fatty acid Substances 0.000 description 33
- 229930195729 fatty acid Natural products 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 229920001296 polysiloxane Polymers 0.000 description 21
- 150000004665 fatty acids Chemical class 0.000 description 17
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 239000000049 pigment Substances 0.000 description 13
- 229910052719 titanium Inorganic materials 0.000 description 13
- 239000010936 titanium Substances 0.000 description 13
- 229910052726 zirconium Inorganic materials 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 12
- 239000002537 cosmetic Substances 0.000 description 11
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 239000013522 chelant Substances 0.000 description 7
- 239000010419 fine particle Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 6
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 239000004375 Dextrin Substances 0.000 description 6
- 229920001353 Dextrin Polymers 0.000 description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 235000019425 dextrin Nutrition 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
- 238000004898 kneading Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 210000003298 dental enamel Anatomy 0.000 description 5
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 5
- 210000004209 hair Anatomy 0.000 description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 4
- 239000004166 Lanolin Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229910008051 Si-OH Inorganic materials 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910006358 Si—OH Inorganic materials 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003240 coconut oil Substances 0.000 description 4
- 235000019864 coconut oil Nutrition 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000001815 facial effect Effects 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- YYVJAABUJYRQJO-UHFFFAOYSA-N isomyristic acid Chemical compound CC(C)CCCCCCCCCCC(O)=O YYVJAABUJYRQJO-UHFFFAOYSA-N 0.000 description 4
- 235000019388 lanolin Nutrition 0.000 description 4
- 229940039717 lanolin Drugs 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 3
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000005639 Lauric acid Substances 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- 235000021314 Palmitic acid Nutrition 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 235000015278 beef Nutrition 0.000 description 3
- 229910000420 cerium oxide Inorganic materials 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 239000002612 dispersion medium Substances 0.000 description 3
- 239000012776 electronic material Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
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- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
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- 239000006210 lotion Substances 0.000 description 3
- 239000006247 magnetic powder Substances 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
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- 230000001590 oxidative effect Effects 0.000 description 3
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 3
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- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 3
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- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 3
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- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 2
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- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- ZONJATNKKGGVSU-UHFFFAOYSA-N 14-methylpentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCC(O)=O ZONJATNKKGGVSU-UHFFFAOYSA-N 0.000 description 2
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- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 2
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- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
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- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 2
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- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- 239000004606 Fillers/Extenders Substances 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- DCWZELMIUJYGMS-UHFFFAOYSA-N tetradecyl 2,2-dimethylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)(C)C DCWZELMIUJYGMS-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 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
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- QPQANCNBWQXGTQ-UHFFFAOYSA-N trihydroxy(trimethylsilylperoxy)silane Chemical compound C[Si](C)(C)OO[Si](O)(O)O QPQANCNBWQXGTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940075466 undecylenate Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- XSMMCTCMFDWXIX-UHFFFAOYSA-N zinc silicate Chemical compound [Zn+2].[O-][Si]([O-])=O XSMMCTCMFDWXIX-UHFFFAOYSA-N 0.000 description 1
- 235000019352 zinc silicate Nutrition 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Cosmetics (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Description
本発明は、有機化合物を被覆した粉体の製造方法に関する。 The present invention relates to a method for producing a powder coated with an organic compound.
粉体の表面に有機化合物を被覆すると、粉体の分散性、貯蔵安定性、使用適性を高めたり、粉体の機能、例えば、皮膚への付着力(付着性)、感触(使用感)、光沢、隠蔽力、着色力、透明性、紫外線や赤外線の遮蔽能、導電性、蛍光性、発光性、触媒活性等を飛躍的に向上させたりすることができる。このため、有機化合物を被覆した粉体は、化粧料、プラスチックの添加剤、インク、塗料、トナー(磁性粉、外添剤)、化学繊維、包装材料、電子材料等の各種分野で広く使用されている。 When the surface of the powder is coated with an organic compound, the dispersibility, storage stability and suitability for use of the powder are improved, and the function of the powder, for example, adhesion to the skin (adhesion), feel (use feeling), Gloss, hiding power, coloring power, transparency, shielding ability of ultraviolet rays and infrared rays, conductivity, fluorescence, luminescence, catalytic activity, etc. can be greatly improved. For this reason, powders coated with organic compounds are widely used in various fields such as cosmetics, plastic additives, inks, paints, toners (magnetic powders, external additives), chemical fibers, packaging materials, and electronic materials. ing.
このような有機化合物被覆粉体は例えば、特許文献1には、粉体表面にオルガノ水素ポリシロキサン化合物を反応させて表面被覆処理を行ったのち、水又は低級アルコールのなかから選ばれた1種以上の化合物を該表面被覆処理粉体に接触させて、被覆層に残存しているオルガノ水素ポリシロキサン化合物中のSi−H結合の水素原子を他の官能基に置換することを特徴とする、表面被覆粉体の処理方法を開示しており、表面被覆粉体の使用段階で発生する水素ガスを抑制することができる。具体的に実施例1には、微粒子酸化チタンとメチルハイドロジェンポリシロキサンと溶媒を、加熱、減圧可能なニーダーに投入し、撹拌しながら加熱減圧を行ない、溶剤を除去し、次いで、装置内を120℃まで加熱した後、水50gを添加し、その温度に保ちながら、水分が無くなるまで常圧で加熱撹拌を行い、パルペライザーで粉砕を行うことを記載している。 Such an organic compound-coated powder is, for example, disclosed in Patent Document 1 as one selected from water or lower alcohol after surface coating treatment by reacting the powder surface with an organohydrogenpolysiloxane compound. The above compound is contacted with the surface-coated powder, and the hydrogen atom of the Si-H bond in the organohydrogenpolysiloxane compound remaining in the coating layer is substituted with another functional group, The processing method of surface covering powder is indicated and hydrogen gas generated at the use stage of surface covering powder can be controlled. Specifically, in Example 1, fine particle titanium oxide, methylhydrogenpolysiloxane and a solvent are put into a kneader capable of heating and depressurizing, heating and depressurizing while stirring to remove the solvent, It describes that after heating to 120 ° C., 50 g of water is added, and the mixture is heated and stirred at normal pressure until no water remains, and pulverized with a pulverizer while maintaining the temperature.
特許文献1の方法で製造した有機化合物被覆粉体では、オルガノ水素ポリシロキサン化合物中のSi−H結合の水素原子を他の官能基に置換して、発生する水素ガス量を抑制することができるものの、Si−OH結合等の生成のために十分な撥水性(親油性)が得られていない。更に、Si−OH結合等の親水性の部分と、Si−OH結合が脱水縮合して形成したSi−O−Si結合等の撥水性の部分の両方が存在するため、有機溶媒中での分散安定性が悪いという問題がある。 In the organic compound-coated powder produced by the method of Patent Document 1, the hydrogen atom of the Si—H bond in the organohydrogenpolysiloxane compound can be replaced with another functional group to suppress the amount of generated hydrogen gas. However, sufficient water repellency (lipophilicity) for generation of Si—OH bonds or the like is not obtained. Furthermore, since both hydrophilic parts such as Si-OH bonds and water-repellent parts such as Si-O-Si bonds formed by dehydration condensation of Si-OH bonds exist, dispersion in organic solvents is possible. There is a problem of poor stability.
そこで、本発明者らは、個々の粒子に有機化合物の被覆をより一層強固に行うとともに、前記の有機化合物のSi−OH結合等を水酸基が残存しないようにするために脱水縮合して例えばシロキサンSi−O−Si結合等に変化させると、水素ガス発生を抑制できるとともに、優れた撥水性(親油性)を有する粉体が製造できると考え、種々研究した結果、(1)少なくとも粉体と加水分解性有機化合物を粉砕及び/又は混合する第一の工程、(2)第一の工程で得られた粉砕物及び/又は混合物を40〜200℃の温度で、かつ、その温度の飽和蒸気圧の50〜100%の条件下で水、低級アルコールから選ばれる少なくとも一種と接触させる第二の工程、(3)第二の工程で得られた粉体を50〜200℃の温度で、かつ、その温度の飽和蒸気圧の50%以下の水、低級アルコールから選ばれる少なくとも一種の存在下あるいはそれらの不存在下で加熱する第三の工程を行うことにより、所望の有機化合物被覆粉体が製造できることを見出し、本発明を完成した。 Accordingly, the inventors of the present invention applied an organic compound to each particle more firmly and dehydrated and condensed, for example, siloxane to prevent Si—OH bonds and the like of the organic compound from remaining. As a result of various studies, it is considered that, when changed to Si—O—Si bonds, etc., hydrogen gas generation can be suppressed and powder having excellent water repellency (lipophilicity) can be produced. A first step of pulverizing and / or mixing the hydrolyzable organic compound; (2) the pulverized product and / or mixture obtained in the first step at a temperature of 40 to 200 ° C. and saturated steam at that temperature; A second step of contacting with at least one selected from water and lower alcohol under a condition of 50 to 100% of the pressure, (3) the powder obtained in the second step at a temperature of 50 to 200 ° C., and Saturating its temperature It is found that a desired organic compound-coated powder can be produced by performing a third step of heating in the presence or absence of at least one kind selected from water and lower alcohols having a vapor pressure of 50% or less, The present invention has been completed.
すなわち、本発明は、(1)少なくとも粉体と加水分解性有機化合物を粉砕及び/又は混合する第一の工程、(2)次いで、第一の工程で得られた粉砕物及び/又は混合物を40〜200℃の温度で、かつ、その温度の飽和蒸気圧の50〜100%の条件下で水、低級アルコールから選ばれる少なくとも一種と接触させる第二の工程、(3)次いで、第二の工程で得られた粉体を50〜200℃の温度で、かつ、その温度の飽和蒸気圧の50%以下の水、低級アルコールから選ばれる少なくとも一種の存在下あるいはそれらの不存在下で加熱する第三の工程を含む、有機化合物被覆粉体の製造方法である。 That is, the present invention includes (1) a first step of pulverizing and / or mixing at least a powder and a hydrolyzable organic compound, and (2) a pulverized product and / or a mixture obtained in the first step. A second step of contacting with at least one selected from water and a lower alcohol at a temperature of 40 to 200 ° C. and under a condition of 50 to 100% of the saturated vapor pressure at that temperature, (3) The powder obtained in the process is heated at a temperature of 50 to 200 ° C. and in the presence of at least one kind selected from water and lower alcohols having a saturated vapor pressure of 50% or less at that temperature, or in the absence thereof. It is a manufacturing method of organic compound covering powder including the 3rd process.
本発明は、加水分解性有機化合物やその加水分解物及び/又は脱水縮合物の被覆を施した粉体を製造する方法であって、水素ガス発生を抑制できるとともに、優れた撥水性(親油性)を有する。このため、本発明により得られる有機化合物被覆粉体は種々の用途に用いることができ、例えば、本発明の被覆粉体を溶媒に分散した分散体や化粧料に配合すると長期間の安定した使用が可能であり、また、粉体の高濃度化も可能となる。 The present invention is a method for producing a powder coated with a hydrolyzable organic compound or a hydrolyzate and / or dehydrated condensate thereof, which can suppress generation of hydrogen gas and has excellent water repellency (lipophilicity). ). For this reason, the organic compound-coated powder obtained by the present invention can be used for various applications. For example, when the coated powder of the present invention is blended in a dispersion or cosmetic material dispersed in a solvent, it can be used stably for a long time. It is also possible to increase the concentration of the powder.
本発明の有機化合物被覆粉体の製造方法は、(1)少なくとも粉体と加水分解性有機化合物を粉砕及び/又は混合する第一の工程、(2)次いで、第一の工程で得られた粉砕物及び/又は混合物を40〜200℃の温度で、かつ、その温度の飽和蒸気圧の50〜100%の条件下で水、低級アルコールから選ばれる少なくとも一種と接触させる第二の工程、(3)次いで、第二の工程で得られた粉体を50〜200℃の温度で、かつ、その温度の飽和蒸気圧の50%以下の水、低級アルコールから選ばれる少なくとも一種の存在下あるいはそれらの不存在下で加熱する第三の工程を含む。 The method for producing an organic compound-coated powder according to the present invention was obtained by (1) a first step of pulverizing and / or mixing at least the powder and the hydrolyzable organic compound, and (2) a first step. A second step of bringing the pulverized product and / or mixture into contact with at least one selected from water and lower alcohols at a temperature of 40 to 200 ° C. and 50 to 100% of a saturated vapor pressure at that temperature; 3) Next, the powder obtained in the second step is at a temperature of 50 to 200 ° C. and in the presence of at least one kind selected from water and lower alcohol at 50% or less of the saturated vapor pressure at that temperature, or those A third step of heating in the absence of
まず、第一の工程は少なくとも粉体と加水分解性有機化合物を粉砕及び/又は混合する工程であり、従来の装置を用いることができる。粉砕機としては、クラッシャー等の破砕機、ボールミル、ビーズミル、コロイドミル、コニカルミル、ディスクミル、エッジミル、製粉ミル、ハンマーミル、乳鉢、ペレットミル、VSIミル、ウィリーミル、ローラーミル、サンドグラインダー、ジェットミル等の粉砕機を適宜用いることができ、特に気流粉砕機が好ましい。気流粉砕機は、高速でアルゴンガスや窒素ガス等をノズルから噴出させ、このガス流によって粉末粒子を加速、互いに衝突させて粉砕する機械であり、ジェットミル、クロスジェットミル、セレンミラー等を用いることができる。混合機としては、ヘンシェルミキサー、リボンミキサー、ナウタミキサー、プラネタリーミキサー、タンブラー、スーパーミキサー、クーリングミキサー、TSK−MTIミキサー、プロペラミキサー、ハイスピードミキサー、リボンブレンダー、縦型円錐混合機、たて型混合機、リボコーン、高速ミキサー、万能混合撹拌機、万能混合機、V型混合機、ダブルコーンブレンダー等を適宜用いることができる。粉砕条件、混合条件は適宜設定することができ、例えば、粉砕、混合の温度は室温が好ましく、粉砕、混合の雰囲気は酸素ガス、大気中等の酸化性雰囲気、窒素ガス、アルゴンガス等の不活性ガス雰囲気、水素ガス等の還元性ガス雰囲気のいずれでもよく、特に不活性ガス雰囲気が好ましい。なお、粉砕機に入れる前に、特に気流粉砕機に入れる前には、粉体と有機化合物とを混合するのが好ましく、ヘンシェルミキサーやスーパーミキサー等の混合機を用いるのが好ましい。粉体と加水分解性有機化合物の混合割合は適宜設定することができ、粉体の重量に対して5〜30重量%程度が好ましく、10〜25重量%がより好ましく、15〜25重量%が更に好ましい。また、粉体と加水分解性有機化合物のほかに必要に応じて、粉砕助剤を添加してもよい。 First, the first step is a step of pulverizing and / or mixing at least the powder and the hydrolyzable organic compound, and a conventional apparatus can be used. Crushers such as crushers, ball mills, bead mills, colloid mills, conical mills, disc mills, edge mills, milling mills, hammer mills, mortars, pellet mills, VSI mills, wheelie mills, roller mills, sand grinders, jet mills A pulverizer such as an air pulverizer is particularly preferable. An airflow pulverizer is a machine that jets argon gas, nitrogen gas, or the like from a nozzle at high speed, and accelerates powder particles by this gas flow and collides with each other to pulverize them, using a jet mill, a cross jet mill, a selenium mirror, etc. be able to. Henschel mixer, ribbon mixer, nauta mixer, planetary mixer, tumbler, super mixer, cooling mixer, TSK-MTI mixer, propeller mixer, high speed mixer, ribbon blender, vertical cone mixer, vertical type A mixer, a ribocone, a high-speed mixer, a universal mixer, a universal mixer, a V-type mixer, a double cone blender, or the like can be used as appropriate. The pulverization and mixing conditions can be set as appropriate. For example, the temperature for pulverization and mixing is preferably room temperature, and the atmosphere for pulverization and mixing is an oxygen gas, an oxidizing atmosphere such as in the air, an inert gas such as nitrogen gas or argon gas. Either a gas atmosphere or a reducing gas atmosphere such as hydrogen gas may be used, and an inert gas atmosphere is particularly preferable. In addition, before putting into a grinder, especially before putting into an airflow grinder, it is preferable to mix powder and an organic compound, and it is preferable to use mixers, such as a Henschel mixer and a super mixer. The mixing ratio of the powder and the hydrolyzable organic compound can be appropriately set, and is preferably about 5 to 30% by weight, more preferably 10 to 25% by weight, and more preferably 15 to 25% by weight based on the weight of the powder. Further preferred. In addition to the powder and the hydrolyzable organic compound, a grinding aid may be added as necessary.
粉体としては、種々の物質を用いることができ、例えば、体質顔料として、マイカ、セリサイト、タルク、クレー、カオリン、合成マイカ、炭酸カルシウム、炭酸マグネシウム、ケイ酸マグネシウム、ケイ酸アルミニウム、リン酸カルシウム、無水ケイ酸、アルミナ、酸化マグネシウム、酸化ジルコニウム、水酸化アルミニウム、硫酸バリウム、ケイ酸アルミン酸マグネシウム、メタケイ酸アルミン酸マグネシウム、窒化ホウ素、ゼオライト、ヒドロキシアパタイト、セラミックパウダー等を挙げることができる。また、白色顔料としては、塩基性炭酸鉛、塩基性硫酸鉛、酸化チタン、酸化亜鉛、酸化セリウム、リン酸亜鉛、リン酸アルミニウム等を、着色顔料としては、ベンガラ、黄酸化鉄、黒酸化鉄、酸化コバルト、酸化クロム、水酸化クロム、紺青、群青、カーボンブラック、低次酸化チタン、マンゴバイオレット、亜酸化銅、黒鉛、黄鉛、カドミウムエロー、カドミウムレッド、コバルトブルー、モリブデートオレンジ等を、蛍光顔料としては、硫化亜鉛、珪酸亜鉛、硫酸亜鉛カドミウム、硫化カルシウム、硫化ストロンチウム、タングステン酸カルシウム等を、パール顔料としては、オキシ塩化ビスマス、雲母チタン、魚鱗箔等を、微粒子粉体としては、微粒子酸化チタン、微粒子酸化亜鉛、微粒子酸化鉄、微粒子酸化セリウム等を、金属光沢顔料としては、アルミニウムパウダー、亜鉛粉、金粉、銀粉、スズ粉、ステンレスパウダー、ダイヤモンドパウダー、銅粉、ニッケルパウダー、ブロンズパウダー等を、蛍光顔料としては硫化亜鉛、タングステン酸カルシウム等を、その他の粉体としては、酸化錫、ATO(アンチモンドープ酸化錫)、ITO(錫ドープ酸化インジウム)、Alドープ酸化亜鉛等をそれぞれ挙げることができる。また、必要に応じてこれらの粉体を複合化したもの又は無機化合物で被覆したものを用いることができる。例えば、微粒子酸化チタン、微粒子酸化亜鉛、微粒子酸化鉄、微粒子酸化セリウム等の微粒子粉体をアルミニウム、カルシウム、マグネシウム、セリウム、ケイ素、ジルコニウム、チタン、亜鉛、鉄、コバルト、マンガン、ニッケル及びスズの少なくとも1種の酸化物又は含水酸化物で被覆した粉体、ベンガラ等の無機着色顔料を無水ケイ酸で被覆した粉体、体質顔料を微粒子白色顔料で被覆した粉体等が挙げられる。 As the powder, various substances can be used. For example, as an extender pigment, mica, sericite, talc, clay, kaolin, synthetic mica, calcium carbonate, magnesium carbonate, magnesium silicate, aluminum silicate, calcium phosphate, Examples thereof include anhydrous silicic acid, alumina, magnesium oxide, zirconium oxide, aluminum hydroxide, barium sulfate, magnesium aluminate silicate, magnesium aluminate metasilicate, boron nitride, zeolite, hydroxyapatite, and ceramic powder. White pigments include basic lead carbonate, basic lead sulfate, titanium oxide, zinc oxide, cerium oxide, zinc phosphate, and aluminum phosphate, and color pigments include bengara, yellow iron oxide, and black iron oxide. , Cobalt oxide, chromium oxide, chromium hydroxide, bitumen, ultramarine, carbon black, low order titanium oxide, mango violet, cuprous oxide, graphite, chrome lead, cadmium yellow, cadmium red, cobalt blue, molybdate orange, etc. As fluorescent pigments, zinc sulfide, zinc silicate, cadmium zinc sulfate, calcium sulfide, strontium sulfide, calcium tungstate, etc., as pearl pigments, bismuth oxychloride, titanium mica, fish scale foil, etc. Fine metallic titanium oxide, fine zinc oxide, fine iron oxide, fine cerium oxide, etc. Aluminum powder, zinc powder, gold powder, silver powder, tin powder, stainless steel powder, diamond powder, copper powder, nickel powder, bronze powder, etc. as the material, zinc sulfide, calcium tungstate, etc. as the fluorescent pigment, and other powders Examples of the body include tin oxide, ATO (antimony-doped tin oxide), ITO (tin-doped indium oxide), and Al-doped zinc oxide. In addition, a composite of these powders or a coating with an inorganic compound can be used as necessary. For example, fine particle powders such as fine particle titanium oxide, fine particle zinc oxide, fine particle iron oxide, fine particle cerium oxide are made of at least aluminum, calcium, magnesium, cerium, silicon, zirconium, titanium, zinc, iron, cobalt, manganese, nickel and tin. Examples thereof include powders coated with one kind of oxide or hydrous oxide, powders coated with inorganic colored pigments such as Bengala with silicic anhydride, and powders coated with extender pigments with fine white pigments.
前記の加水分解性有機化合物としては、アルコキシ基、ハロゲン原子、水素原子等の加水分解性基を有する有機化合物を用いることができる。このような有機化合物としては例えば、有機ケイ素化合物、有機チタン化合物、有機アルミニウム化合物、有機ジルコニウム化合物から選らばれる少なくとも一種がより好ましく、シランカップリング剤、チタンカップリング剤、アルミニウムカップリング剤、ジルコニウムカップリング剤、シランアルコキシド、チタンアルコキシド、アルミニウムアルコキシド、ジルコニウムアルコキシド、シラン有機キレート、チタン有機キレート、アルミニウム有機キレート、ジルコニウム有機キレート、シランアシレート、チタンアシレート、アルミニウムアシレート、ジルコニウムアシレート等を用いることができる。 As said hydrolysable organic compound, the organic compound which has hydrolysable groups, such as an alkoxy group, a halogen atom, and a hydrogen atom, can be used. As such an organic compound, for example, at least one selected from an organosilicon compound, an organotitanium compound, an organoaluminum compound, and an organozirconium compound is more preferable. A silane coupling agent, a titanium coupling agent, an aluminum coupling agent, a zirconium cup Use ring agent, silane alkoxide, titanium alkoxide, aluminum alkoxide, zirconium alkoxide, silane organic chelate, titanium organic chelate, aluminum organic chelate, zirconium organic chelate, silane acylate, titanium acylate, aluminum acylate, zirconium acylate, etc. Can do.
シランカップリング剤としては具体的に、ビニルトリメトキシシラン、γ−グリシドキシプロピルトリメトキシシラン(GPS)、γ−メタクリロキシプロピルトリメトキシシラン(MPS)、γ−アミノプロピルトリメトキシシラン(APS)、N−β(アミノエチル)γ−アミノプロピルトリメトキシシラン(AEAPS)、N−フェニル−γ−アミノプロピルトリメトキシシラン(AnPS)、γ-メルカプトプロピルトリメトキシシラン(MGPS)などを用いることができる。 Specific examples of silane coupling agents include vinyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane (GPS), γ-methacryloxypropyltrimethoxysilane (MPS), and γ-aminopropyltrimethoxysilane (APS). N-β (aminoethyl) γ-aminopropyltrimethoxysilane (AEAPS), N-phenyl-γ-aminopropyltrimethoxysilane (AnPS), γ-mercaptopropyltrimethoxysilane (MGPS), etc. can be used. .
また、有機ケイ素化合物としてはアルコキシポリシロキサン、オルガノハイドロジェンポリシロキサン、オルガノハイドロジェンシロキサン−ジメチルシロキサン共重合体、アルコキシシランから選ばれる少なくとも一種が更に好ましい。アルコキシポリシロキサンは、ジクロロジメチルシラン等のシラン類を加水分解し、生成したシラノールが脱水縮合したオリゴマー又はポリマーであり、アルコキシ基や変性アルコキシ基を有するものである。例えば、ジメトキシポリシロキサン、トリメトキシポリシロキサン等が用いられる。また、オルガノハイドロジェンポリシロキサンとしては、メチルハイドロジェンポリシロキサン等が挙げられ、重合度nが3〜7の整数であることがより好ましい。オルガノハイドロジェンシロキサン−ジメチルシロキサン共重合体としては、メチルハイドロジェンシロキサン−ジメチルシロキサン共重合体等が挙げられ、それはジメチコン/メチコンコポリマーともいわれ、その基本化学構造は、次の一般式(I)で表され、本発明においては、一般式(I)におけるm、nが、m=7〜14、n=3〜8であり、m+nが、m+n=10〜22のものが好ましい。また、アルコキシシランとしては、メチルトリメトキシシラン、エチルトリエトキシシラン、オクチルトリエトキシシラン等が挙げられる。また、トリオルガノシロキシケイ酸等を用いることもできる。トリメチルシロキシケイ酸は、水ガラスのナトリウムをトリメチルシリル基で置換して得られたものを溶媒に溶解したものである。 The organosilicon compound is more preferably at least one selected from alkoxypolysiloxane, organohydrogenpolysiloxane, organohydrogensiloxane-dimethylsiloxane copolymer, and alkoxysilane. The alkoxypolysiloxane is an oligomer or polymer obtained by hydrolyzing silanes such as dichlorodimethylsilane and dehydrating condensation of the produced silanol, and has an alkoxy group or a modified alkoxy group. For example, dimethoxypolysiloxane, trimethoxypolysiloxane and the like are used. Examples of the organohydrogenpolysiloxane include methylhydrogenpolysiloxane, and the polymerization degree n is more preferably an integer of 3 to 7. Examples of the organohydrogensiloxane-dimethylsiloxane copolymer include methylhydrogensiloxane-dimethylsiloxane copolymer, which is also referred to as dimethicone / methicone copolymer, and its basic chemical structure is represented by the following general formula (I). In the present invention, m and n in formula (I) are preferably m = 7 to 14, n = 3 to 8, and m + n is preferably m + n = 10 to 22. Examples of the alkoxysilane include methyltrimethoxysilane, ethyltriethoxysilane, octyltriethoxysilane, and the like. Triorganosiloxysilicic acid or the like can also be used. Trimethylsiloxysilicic acid is obtained by dissolving sodium in water glass with a trimethylsilyl group and dissolving it in a solvent.
有機チタン化合物としては、アミン系、亜リン酸(ホスファイト)型、ピロリン酸型、カルボン酸型等のチタンカップリング剤、チタンテトライソプロポキシド、チタンテトラノルマルブトキシド、チタンブトキシドダイマー、チタンテトラ−2−エチルヘキソキシド等のチタンアルコキシド、アセチルアセトンキレート等のチタンキレート、チタンアシレートなどを用いることができる。また、有機アルミニウム化合物としては、アセトアルコキシアルミニウムジイソプロピレート等のアルミニウムカップリング剤、アルミニウムイソプロポキシド等のアルミニウムアルコキシドなどを用いることができる。有機ジルコニウム化合物としては、ジルコニウムノルマルプロポキシド、ジルコニウムノルマルブトキシド、アセチルアセトンキレート等のジルコニウムキレート、ジルコニウムアシレートなどを用いることができる。その他の加水分解性化合物としては、有機リン酸化合物、有機スズ化合物、有機亜鉛化合物等を用いることができる。 Examples of the organic titanium compound include amine-based, phosphorous acid (phosphite) type, pyrophosphoric acid type, carboxylic acid type titanium coupling agents, titanium tetraisopropoxide, titanium tetranormal butoxide, titanium butoxide dimer, titanium tetra- Titanium alkoxides such as 2-ethylhexoxide, titanium chelates such as acetylacetone chelate, titanium acylate, and the like can be used. As the organoaluminum compound, an aluminum coupling agent such as acetoalkoxyaluminum diisopropylate, an aluminum alkoxide such as aluminum isopropoxide, and the like can be used. As the organic zirconium compound, zirconium chelate such as zirconium normal propoxide, zirconium normal butoxide, and acetylacetone chelate, zirconium acylate, and the like can be used. As other hydrolyzable compounds, organophosphate compounds, organotin compounds, organozinc compounds, and the like can be used.
前記の加水分解性有機化合物に加えて種々の化合物を添加し被覆してもよい。このような化合物として、ポリシロキサン、アルキルシラン、脂肪酸又はその塩、ポリオレフィン、水添レシチン又はその塩、N−アシルアミノ酸又はその塩、デキストリン脂肪酸エステル等が挙げられる。ポリシロキサンは、ジクロロジメチルシラン等のシラン類を加水分解し、生成したシラノールが脱水縮合したオリゴマー又はポリマーである。ポリシロキサンとしては例えば、ジメチルポリシロキサン、変性オルガノポリシロキサン等のオルガノポリシロキサン、シリコーンポリマー、トリオルガノシロキシケイ酸などのシラノールが脱水縮合したオリゴマー又はポリマーを含む化合物である。 In addition to the hydrolyzable organic compound, various compounds may be added and coated. Examples of such a compound include polysiloxane, alkylsilane, fatty acid or salt thereof, polyolefin, hydrogenated lecithin or salt thereof, N-acylamino acid or salt thereof, dextrin fatty acid ester and the like. Polysiloxane is an oligomer or polymer obtained by hydrolyzing silanes such as dichlorodimethylsilane and dehydrating condensation of the generated silanol. Examples of the polysiloxane include a compound containing an oligomer or a polymer obtained by dehydration condensation of an organopolysiloxane such as dimethylpolysiloxane or modified organopolysiloxane, a silicone polymer, or triorganosiloxysilicate.
具体的には、オルガノポリシロキサンとしては、ジメチルポリシロキサンが挙げられ、それはジメチコンともいわれ、その基本化学構造は、次の一般式(II)で表される。一般式(II)におけるnが、n=1〜400のものが好ましく、粘度は概ね1〜1000センチストークスのものが好ましい。 Specifically, examples of the organopolysiloxane include dimethylpolysiloxane, which is also called dimethicone, and its basic chemical structure is represented by the following general formula (II). In the general formula (II), n is preferably n = 1 to 400, and the viscosity is preferably about 1 to 1000 centistokes.
また、アルキルシランとしては、メチルシラン、エチルシラン、オクチルシラン等が挙げられる。脂肪酸としては、例えばカプリル酸、カプリン酸、ラウリン酸、ミリスチン酸、イソミリスチン酸、パルミチン酸、イソパルミチン酸、ステアリン酸、イソステアリン酸、アラキン酸、ウンデシレン酸、オレイン酸、ミリストレイン酸、エライジン酸、リノール酸、リノレン酸、アラキドン酸、ヤシ油脂肪酸、牛脂脂肪酸、樹脂酸(アビエチン酸)、それらの塩、それらの金属塩等を挙げることができる。 Examples of the alkyl silane include methyl silane, ethyl silane, octyl silane and the like. Examples of fatty acids include caprylic acid, capric acid, lauric acid, myristic acid, isomyristic acid, palmitic acid, isopalmitic acid, stearic acid, isostearic acid, arachidic acid, undecylenic acid, oleic acid, myristoleic acid, elaidic acid, Examples thereof include linoleic acid, linolenic acid, arachidonic acid, coconut oil fatty acid, beef tallow fatty acid, resin acid (abietic acid), salts thereof, and metal salts thereof.
また、ポリオレフィンとしてはポリエチレン、ポリプロピレン等を用いることができ、例えば、分子量500〜20000で融点が40℃以上の低分子ポリエチレンや、ポリプロピレンを酸化して得られる酸化ポリエチレン、マレイン化ポリエチレン、酸化ポリプロピレン等の市販品を使用することができる。 In addition, polyethylene, polypropylene, and the like can be used as the polyolefin. For example, low molecular polyethylene having a molecular weight of 500 to 20000 and a melting point of 40 ° C. or more, polyethylene oxide obtained by oxidizing polypropylene, maleated polyethylene, polypropylene oxide, and the like. Commercial products can be used.
水添レシチンとしては、卵黄、大豆、コーン、菜種等から抽出された天然のレシチンや合成レシチンを水素添加したもので、ヨウ素価が好ましくは30以下、より好ましくは15以下の水添レシチンであり、リン酸基を有するグリセライドである。塩の形態にあるものとしては、Al、Mg、Ca、Zn、Zr、Ti等の水不溶性水添レシチン金属塩が好ましい。 Hydrogenated lecithin is a hydrogenated natural lecithin or synthetic lecithin extracted from egg yolk, soybean, corn, rapeseed, etc., and has an iodine value of preferably 30 or less, more preferably 15 or less. And a glyceride having a phosphate group. As the salt form, a water-insoluble hydrogenated lecithin metal salt such as Al, Mg, Ca, Zn, Zr and Ti is preferable.
また、N−アシルアミノ酸は、アミノ酸のアミノ基及び/又はイミノ基がアシル化されたものである。アミノ酸の種類としては、グリシン、アラニン、β−アラニン、バリン、ロイシン、イソロイシン、フェニルアラニン、プロリン、スレオニン、セリン、アルギニン、ヒスチジン、リジン、アスパラギン酸、グルタミン酸、チロシン、メチオニン、シスチン、システイン等を挙げることができる。 N-acylamino acids are those in which the amino group and / or imino group of the amino acid is acylated. Examples of amino acid types include glycine, alanine, β-alanine, valine, leucine, isoleucine, phenylalanine, proline, threonine, serine, arginine, histidine, lysine, aspartic acid, glutamic acid, tyrosine, methionine, cystine, cysteine, etc. Can do.
N−アシル体を構成する脂肪酸は、長鎖脂肪酸が好ましく、例えばカプリル酸、カプリン酸、ラウリン酸、ミリスチン酸、イソミリスチン酸、パルミチン酸、イソパルミチン酸、ステアリン酸、イソステアリン酸、アラキン酸、ウンデシレン酸、オレイン酸、ミリストレイン酸、エライジン酸、リノール酸、リノレン酸、アラキドン酸、ヤシ油脂肪酸、牛脂脂肪酸、樹脂酸(アビエチン酸)等を挙げることができる。塩の形態としてはNa、K、Ba、Zn、Ca、Mg、Fe、Zr、Co、Al、Zr、Ti等の金属塩や、アンモニウム塩、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、2−アミノ−2−メチル−プロパノール、2−アミノ−2−メチル−1,3−プロパンジオール、トリイソプロパノールアミン等の各種アルカノールアミン塩等を挙げることができる。 The fatty acid constituting the N-acyl is preferably a long-chain fatty acid, for example, caprylic acid, capric acid, lauric acid, myristic acid, isomyristic acid, palmitic acid, isopalmitic acid, stearic acid, isostearic acid, arachidic acid, undecylenate. Examples thereof include acid, oleic acid, myristoleic acid, elaidic acid, linoleic acid, linolenic acid, arachidonic acid, coconut oil fatty acid, beef tallow fatty acid, and resin acid (abietic acid). As salt forms, metal salts such as Na, K, Ba, Zn, Ca, Mg, Fe, Zr, Co, Al, Zr, Ti, ammonium salts, monoethanolamine, diethanolamine, triethanolamine, 2-amino Examples thereof include various alkanolamine salts such as 2-methyl-propanol, 2-amino-2-methyl-1,3-propanediol, and triisopropanolamine.
また、デキストリン脂肪酸エステルとしては、デキストリンと脂肪酸とで構成されるエステルあるいはその誘導体から選択することができる。好ましくは、デキストリン1分子に対し、その水酸基の1つに炭素数8〜24の脂肪酸の1分子がエステル化した部分構造を少なくとも有するエステル体あるいはその誘導体、例えばデキストリン1分子に対し炭素数8〜24の脂肪酸が1個又は複数個有し、その水酸基の1個又は複数個にエステル結合した構造を有するエステル体や当該エステル体において水酸基が更に別種の脂肪酸でエステル化された誘導体等を挙げることができる。 Moreover, as dextrin fatty acid ester, it can select from the ester comprised from dextrin and a fatty acid, or its derivative (s). Preferably, for one dextrin molecule, an ester having at least a partial structure in which one molecule of a fatty acid having 8 to 24 carbon atoms is esterified to one of its hydroxyl groups, or a derivative thereof, such as 8 to 8 carbon atoms for one molecule of dextrin Examples include ester bodies having a structure in which one or a plurality of 24 fatty acids and one or more of the hydroxyl groups are ester-bonded, derivatives in which the hydroxyl groups are further esterified with other fatty acids in the ester bodies, etc. Can do.
次に、第二の工程は、第一の工程で得られた粉砕物及び/又は混合物を加熱・調湿処理する工程であり、加水分解性有機化合物を加水分解する工程である。加熱温度は40〜200℃の温度であり、80〜150℃が好ましい。調湿条件は、水、低級アルコールから選ばれる少なくとも一種を添加し、その温度での飽和蒸気圧の50〜100%に調湿する条件下で接触させる。調湿の好ましい条件は、80〜95%である。低級アルコールとしては、メタノール、エタノール、プロパノール等を用いることができる。加熱・調湿処理の時間は適宜設定することができ、例えば1〜12時間が好ましく、2〜8時間がより好ましい。このような加熱・調湿処理は、恒温恒湿器等の温度と湿度を制御できる装置で行うことができる。 Next, the second step is a step of heating / humidifying the pulverized product and / or mixture obtained in the first step and hydrolyzing the hydrolyzable organic compound. The heating temperature is 40 to 200 ° C, preferably 80 to 150 ° C. As the humidity control condition, at least one selected from water and lower alcohol is added, and contact is made under the condition of adjusting the humidity to 50 to 100% of the saturated vapor pressure at that temperature. Preferable conditions for humidity control are 80 to 95%. As the lower alcohol, methanol, ethanol, propanol or the like can be used. The time for the heating / humidifying treatment can be appropriately set, and for example, 1 to 12 hours is preferable and 2 to 8 hours is more preferable. Such heating / humidification treatment can be performed by an apparatus capable of controlling temperature and humidity, such as a constant temperature and humidity chamber.
次に、第三の工程は、第二の工程で得られた粉体を加熱処理する工程であり、被覆をより一層強固にすることができる。また、前記有機化合物が金属化合物の場合、第二の工程で生成したM−OH結合を脱水縮合してM−O−M結合に変化させることもできる。ここで、Mはケイ素、チタン、アルミニウム、ジルコニウム等の金属元素を表す。加熱温度は50〜200℃の温度であり、100〜150℃が好ましい。湿度は、できる限り低いのが好ましく、その温度での飽和蒸気圧の50%以下の水、低級アルコールから選ばれる少なくとも一種の存在下あるいはそれらの不存在下で行う。調湿の好ましい条件は0〜40%であり、0〜30%が更に好ましい。加熱処理の時間は適宜設定することができ、例えば1〜12時間が好ましく、2〜8時間がより好ましい。加熱雰囲気は酸素ガス、大気中等の酸化性雰囲気、窒素ガス、アルゴンガス等の不活性ガス雰囲気、水素ガス等の還元性ガス雰囲気のいずれでもよく、特に不活性ガス雰囲気が好ましい。このような加熱処理は、乾燥器、焼成炉等の温度を制御できる装置で行うことができる。また、この後に必要に応じて、被覆粉体をヘンシェルミキサーやスーパーミキサー等の混合機、ボールミルやサンドグラインダー等のミルで粉砕してもよい。このようにして、本発明の有機化合物被覆粉体を製造することができる。粉体の有機化合物の被覆量は適宜設定することができ、粉体の重量に対して5〜30重量%程度が好ましく、10〜25重量%がより好ましく、15〜25重量%が更に好ましい。 Next, a 3rd process is a process of heat-processing the powder obtained at the 2nd process, and can make a coating | cover still stronger. Further, when the organic compound is a metal compound, the M-OH bond generated in the second step can be dehydrated and condensed to be changed to a MOM bond. Here, M represents a metal element such as silicon, titanium, aluminum, or zirconium. The heating temperature is 50 to 200 ° C, preferably 100 to 150 ° C. The humidity is preferably as low as possible, and is carried out in the presence or absence of at least one kind selected from water and lower alcohol, which are 50% or less of the saturated vapor pressure at that temperature. The preferable condition of humidity control is 0 to 40%, more preferably 0 to 30%. The time for the heat treatment can be appropriately set. For example, 1 to 12 hours is preferable, and 2 to 8 hours is more preferable. The heating atmosphere may be any of an oxygen gas, an oxidizing atmosphere such as air, an inert gas atmosphere such as nitrogen gas and argon gas, and a reducing gas atmosphere such as hydrogen gas, and an inert gas atmosphere is particularly preferable. Such heat treatment can be performed by an apparatus capable of controlling the temperature, such as a dryer or a baking furnace. Further, after that, the coated powder may be pulverized by a mixer such as a Henschel mixer or a super mixer, or a mill such as a ball mill or a sand grinder, if necessary. In this way, the organic compound-coated powder of the present invention can be produced. The coating amount of the organic compound in the powder can be appropriately set, and is preferably about 5 to 30% by weight, more preferably 10 to 25% by weight, and still more preferably 15 to 25% by weight based on the weight of the powder.
このようにして製造した有機化合物被覆粉体は、溶媒に分散させて分散体とすることができる。被覆粉体の濃度は適宜調整することができるが、より高い濃度が好ましい。具体的には、10〜75重量%が好ましく、10〜65重量%がより好ましく、30〜60重量%が更に好ましい。 The organic compound-coated powder thus produced can be dispersed in a solvent to form a dispersion. The concentration of the coating powder can be adjusted as appropriate, but a higher concentration is preferable. Specifically, 10 to 75% by weight is preferable, 10 to 65% by weight is more preferable, and 30 to 60% by weight is still more preferable.
前記の分散体中の分散媒としては、特に限定されず、適宜種々のもの用いることができ、親油性分散媒を好適に用いることができる。具体的には、エタノール、プロピルアルコール、イソプロピルアルコール、ブタノール、アミルアルコール、ヘキシルアルコール、ヘプチルアルコール、オクチルアルコール、カプリルアルコール、ノニルアルコール、デシルアルコール、フェノール、ベンジルアルコール等の一価アルコール系溶剤類、ノルマルペンタン、ノルマルヘキサン、ノルマルヘプタン、ノルマルオクタン、イソヘキサン、イソオクタン、ガソリン、ミネラルスピリット等の石油系炭化水素類、ベンゼン、トルエン、キシレン、シクロヘキサン、エチルベンゼン、アミルベンゼン等の芳香属炭化水素系溶剤類、ジペンテン、テレビン油等の植物系炭化水素系溶剤類、ニトロパラフィン、ニトロベンゼン等のニトロ炭化水素系溶剤類、アセトン、メチルエチルケトン、メチルイソブチルケトン、エチルブチルケトン、ジイソブチルケトン等のケトン系溶剤類、塩化メチレン、クロロホルム、四塩化炭素、パークロルエチレン、モノクロルベンゼン等のハロゲン化炭化水素系溶剤類、エチルエーテル、イソプロピルエーテル、ブチルエーテル、ヘキシルエーテル、プロピレンオキシド、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテル等のエーテル系溶剤類、ぎ酸メチル、ぎ酸エチル、ぎ酸ブチル、酢酸メチル、酢酸エチル、酢酸ブチル、酢酸アミル、プロピオン酸エチル、プロピオン酸ブチル、プロピオン酸イソブチル、酪酸エチル、酪酸ブチル、乳酸メチル、乳酸エチル、乳酸ブチル、乳酸アミル等のエステル系溶剤類、サフラワー油、大豆油、月見草油、ブドウ種子油、ローズヒップ油、ククイナッツ油、アルモンド油、ゴマ油、コムギ胚芽油、トウモロコシ油、綿実油、アボガド油、オリーブ油、ツバキ油、パーシック油、ヒマシ油、ラッカセイ油、ヘーゼルナッツ油、マカデミアナッツ油、メドフォーム油、カカオ脂、シア脂、木ロウ、ヤシ油、パーム油、パーム核油、牛脂、馬脂、ミンク油、乳脂、卵黄油、タートル油等の油脂類、流動パラフィン、流動イソパラフィン、スクワラン、スクワレン、ワセリン、パラフィン、セレシン、マイクロクリスタリンワックス等の炭化水素油類、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、ベヘン酸、オレイン酸、リノール酸、ウンデシレン酸、ヒドロキシステアリン酸、ラノリン脂肪酸等の脂肪酸、ミリスチルアルコール、セチルアルコール、セトステアリルアルコール、ステアリルアルコール、アラルキルアルコール、ベヘニルアルコール、オレイルアルコール、ホホバアルコール、バチルアルコール、コレステロール、フィトステロール、ラノリンアルコール、イソステアリルアルコール等の高級アルコール類、イソステアリン酸イソプロピル、オレイン酸エチル、ミリスチン酸イソプロピル、パルミチン酸イソイソプロピル、オクタン酸セチル、リンゴ酸ジイソステアリル、トリカプリル酸グリセリル、イソノナン酸イソオクチル、イソノナン酸イソノニル、イソノナン酸イソトリデシル、ネオペンタン酸オクチルドデシル、ネオペンタン酸イソトリデシル、ネオペンタン酸ミリスチル、ジイソノナン酸プロピレングリコール、トリ2−エチルヘキサン酸グリセリル、トリ2−エチルヘキサン酸トリメチロールプロパン等のエステル油類、ミツロウ、カンデリラロウ、鯨ロウ、綿ロウ、カルナウバロウ、ベイベリーロウ、ヌカロウ、イボタロウ、オレンジラッフィー油、モンタンロウ、サトウキビロウ、セラックロウ、ラノリン、ホホバオイル、等のロウ類、メチルポリシロキサン、メチルフェニルポリシロキサン、デカメチルシクロテトラシロキサン、アルキル変性シリコーン、アルコール変性シリコーン、アミノ変性シリコーン、エポキシ変性シリコーン、オレフィン変性シリコーン、カルボキシル変性シリコーン、カルビノール変性シリコーン、フェノール変性シリコーン、メタクリル変性シリコーン、メルカプト変性シリコーン、リン酸変性シリコーン、フッ素変性シリコーン、高級脂肪酸変性シリコーン、ポリエーテル変性シリコーン等のシリコーン類、パーフルオロポリエーテル、ハイドロフルオロエーテル、パーフルオロメチルシクロペンタン、パーフルオロジメチルシクロヘキサン、パーフルオロジメチルシクロブタン、メトキシノナフルオロブタン、エトキシノナフルオロブタン、ドデカフルオロペンタン、テトラデカフルオロヘキサン、パーフルオロデカン、パーフルオロオクタン、4−トリトリフルオロメチルパーフルオロモルホリン、4−ペンタフルオロエチルパーフルオロモルホリン等のフッ素系油剤、UV吸収剤としてパラアミノ安息香酸、パラアミノ安息香酸モノグリセリンエステル、N,N−ジメチルパラアミノ安息香酸エチルエステル、N,N−ジエトキシパラアミノ安息香酸エチルエステル、N,N−ジプロポキシパラアミノ安息香酸エチルエステル等の安息香酸類、ホモメンチル−N−アセチルアントラニレート等のアントラニル酸類、アミルサリシレート、メンチルサリシレート、ホモメンチルサリシレート、オクチルサリシレート、フェニルサリシレート、ベンジルサリシレート等のサリチル酸類、オクチルシンナメート、エチル−4−イソプロピルシンナメート、メチル−2,5−ジイソプロピルシンナメート、エチル−2,4−ジイソプロピルシンナメート、プロピル−p−メトキシシンナメート、イソプロピル−p−メトキシシンナメート、イソアミル−p−メトキシシンナメート、オクチル−p−メトキシシンナメート、2−エトキシエチル−p−メトキシシンナメート、シクロヘキシル−p−メトキシシンナメート等の桂皮酸類、2,4−ジヒドロキシベンゾフェノン、2,2'−ジヒドロキシ−4−メトキシベンゾフェノン、2−ヒドロキシ−4−メトキシベンゾフェノン、2−ヒドロキシ−4−メトキシベンゾフェノン−5−スルホン酸塩、4−フェニルベンゾフェノン、4−ヒドロキシ−3−カルボキシベンゾフェノン等のベンゾフェノン類、3−ベンジリデン−d,l−カンファー、ウロカニン酸、ウロカニン酸エチルエステル、2−フェニル−5−メチルベンゾキサゾール、ジベンザラジン、ジアニソイルメタン、4−tert−ブチル−4'−メトキシジベンゾイルメタン、シリコーン変性紫外線吸収剤、フッ素変性紫外線吸収剤等が挙げられる。これらのうち1種又は2種以上を本発明において親油性溶媒として使用できる。 The dispersion medium in the dispersion is not particularly limited, and various types can be used as appropriate, and a lipophilic dispersion medium can be suitably used. Specifically, monohydric alcohol solvents such as ethanol, propyl alcohol, isopropyl alcohol, butanol, amyl alcohol, hexyl alcohol, heptyl alcohol, octyl alcohol, capryl alcohol, nonyl alcohol, decyl alcohol, phenol and benzyl alcohol, normal Petroleum hydrocarbons such as pentane, normal hexane, normal heptane, normal octane, isohexane, isooctane, gasoline, mineral spirits, aromatic hydrocarbon solvents such as benzene, toluene, xylene, cyclohexane, ethylbenzene, amylbenzene, dipentene , Plant hydrocarbon solvents such as turpentine oil, nitro hydrocarbon solvents such as nitroparaffin and nitrobenzene, acetone, methyl ethyl ketone, Ketone solvents such as til isobutyl ketone, ethyl butyl ketone, diisobutyl ketone, halogenated hydrocarbon solvents such as methylene chloride, chloroform, carbon tetrachloride, perchlorethylene, monochlorobenzene, ethyl ether, isopropyl ether, butyl ether, Ether solvents such as hexyl ether, propylene oxide, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, methyl formate, ethyl formate, butyl formate, methyl acetate, ethyl acetate, butyl acetate, acetic acid Ester solvents such as amyl, ethyl propionate, butyl propionate, isobutyl propionate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, butyl lactate, amyl lactate, safra -Oil, soybean oil, evening primrose oil, grape seed oil, rosehip oil, cucumber nut oil, almond oil, sesame oil, wheat germ oil, corn oil, cottonseed oil, avocado oil, olive oil, camellia oil, persic oil, castor oil, peanut oil Oils such as hazelnut oil, macadamia nut oil, medofoam oil, cocoa butter, shea butter, tree wax, coconut oil, palm oil, palm kernel oil, beef tallow, horse fat, mink oil, milk fat, egg yolk oil, turtle oil, Liquid paraffin, liquid isoparaffin, squalane, squalene, petrolatum, paraffin, ceresin, microcrystalline wax and other hydrocarbon oils, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, undecylenic acid, Fatty acids such as hydroxystearic acid and lanolin fatty acid, milli Still alcohol, cetyl alcohol, cetostearyl alcohol, stearyl alcohol, aralkyl alcohol, behenyl alcohol, oleyl alcohol, jojoba alcohol, batyl alcohol, higher alcohols such as cholesterol, phytosterol, lanolin alcohol, isostearyl alcohol, isopropyl isostearate, ethyl oleate , Isopropyl myristate, isoisopropyl palmitate, cetyl octanoate, diisostearyl malate, glyceryl tricaprylate, isooctyl isononanoate, isononyl isononanoate, isotridecyl isononanoate, octyldodecyl neopentanoate, isotridecyl neopentanoate, myristyl neopentanoate, diisononane Propylene glycol acid, tri-2- Ester oils such as glyceryl tilhexanoate, trimethylolpropane tri-2-ethylhexanoate, beeswax, candelilla wax, whale wax, cotton wax, carnauba wax, bayberry wax, nukarou, ibotarou, orange luffy oil, montan wax, sugarcane wax, shellac wax, lanolin , Jojoba oil, waxes, methylpolysiloxane, methylphenylpolysiloxane, decamethylcyclotetrasiloxane, alkyl-modified silicone, alcohol-modified silicone, amino-modified silicone, epoxy-modified silicone, olefin-modified silicone, carboxyl-modified silicone, carbinol Modified silicone, phenol modified silicone, methacryl modified silicone, mercapto modified silicone, phosphoric acid modified silicone, fluorine modified silicone Silicones such as corn, higher fatty acid-modified silicone, polyether-modified silicone, perfluoropolyether, hydrofluoroether, perfluoromethylcyclopentane, perfluorodimethylcyclohexane, perfluorodimethylcyclobutane, methoxynonafluorobutane, ethoxynonafluorobutane Fluorine oils such as dodecafluoropentane, tetradecafluorohexane, perfluorodecane, perfluorooctane, 4-trifluoromethylperfluoromorpholine, 4-pentafluoroethylperfluoromorpholine, paraaminobenzoic acid, paraamino as UV absorber Benzoic acid monoglycerin ester, N, N-dimethylparaaminobenzoic acid ethyl ester, N, N-diethoxyparaaminobenzoic acid ethyl Benzoic acids such as ethyl ester, N, N-dipropoxyparaaminobenzoic acid ethyl ester, anthranilic acids such as homomenthyl-N-acetylanthranilate, amyl salicylate, menthyl salicylate, homomenthyl salicylate, octyl salicylate, phenyl salicylate, benzyl salicylate, etc. Salicylic acids, octylcinnamate, ethyl-4-isopropylcinnamate, methyl-2,5-diisopropylcinnamate, ethyl-2,4-diisopropylcinnamate, propyl-p-methoxycinnamate, isopropyl-p-methoxycinna Mate, isoamyl-p-methoxycinnamate, octyl-p-methoxycinnamate, 2-ethoxyethyl-p-methoxycinnamate, cyclohexyl-p-methoxycinnamate Cinnamic acids such as namate, 2,4-dihydroxybenzophenone, 2,2′-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4 -Benzophenones such as phenylbenzophenone and 4-hydroxy-3-carboxybenzophenone, 3-benzylidene-d, l-camphor, urocanic acid, urocanic acid ethyl ester, 2-phenyl-5-methylbenzoxazole, dibenzalazine, dianisoyl Examples thereof include methane, 4-tert-butyl-4′-methoxydibenzoylmethane, a silicone-modified ultraviolet absorber, a fluorine-modified ultraviolet absorber. Of these, one or more can be used as the lipophilic solvent in the present invention.
また、本発明の分散体には、顔料分散剤、油剤、界面活性剤、紫外線吸収剤、防腐剤、酸化防止剤、皮膜形成剤、保湿剤、増粘剤、染料、顔料、香料等を適宜配合することができる。 In addition, pigment dispersions, oils, surfactants, ultraviolet absorbers, preservatives, antioxidants, film forming agents, humectants, thickeners, dyes, pigments, fragrances and the like are appropriately added to the dispersion of the present invention. Can be blended.
例えばPOEラウリル硫酸トリエタノールアミン等のアルキルエーテル硫酸エステル塩、ドデシルベンゼンスルホン酸ナトリウム等のアルキルベンゼンスルホン酸塩、ラウリル硫酸ナトリウム、ラウリル硫酸カリウム等の高級アルキル硫酸エステル塩、N−アシルサルコシン酸、N−ミリストイル−N−メチルタウリンナトリウム等の高級脂肪酸アミドスルホン酸塩、硬化ヤシ油脂肪酸グリセリン硫酸ナトリウム等の高級脂肪酸エステル硫酸エステル塩、高級脂肪酸エステルスルホン酸塩、高級脂肪酸アルキロールアミド硫酸エステル塩、脂肪酸セッケン、スルホコハク酸塩、二級アルコール硫酸エステル塩、POEアルキルエーテルカルボン酸、POEアルキルアリルエーテルカルボン酸塩、α−オレフィンスルホン酸塩、ラウロイルモノエタノールアミドコハク酸ナトリウム、N−パルミトイルアスパラギン酸ジエタノールアミン、カゼインナトリウム等のアニオン系界面活性剤、塩化ステアリルトリメチルアンモニウム等のアルキルトリメチルアンモニウム塩、塩化ジステアリルジメチルアンモニウムジアルキルジメチルアンモニウム塩等のアルキルピリジニウム塩、アルキル四級アンモニウム塩、アルキルアミン塩、アルキルジメチルベンジルアンモニウム塩、アルキルイソキノリニウム塩、ジアルキルモリホニウム塩、POEアルキルアミン、ポリアミン脂肪酸誘導体、アミルアルコール脂肪酸誘導体、塩化ベンザルコニウム、塩化ベンゼトニウム等のカチオン系界面活性剤、2−ココイル−2−イミタゾリニウムヒドロキサイド−1−カルボキシエチロキシ2ナトリウム塩等のイミダゾリン系両性界面活性剤、アルキルベタイン、アミドベタイン、ラウリルジメチルアミノ酢酸ベタイン等のベタイン系両性界面活性剤、セスキオレイン酸グリセリン、モノステアリン酸グリセリン等のグリセリン脂肪酸エステル、ポリリシノール酸ヘキサグリセリル、モノステアリン酸ジグリセリル、デカオレイン酸デカグリセリル等のポリグリセリン脂肪酸エステル、ソルビタンモノオレート、ソルビタンセスキオレエート等のソルビタン脂肪酸エステル、モノステアリン酸プロピレングリコール等のプロピレングリコール脂肪酸エステル、POEソルビタンモノオレート等のPOEソルビタン脂肪酸エステル、POEグリセリントリイソステアレート等のPOEグリセリン脂肪酸エステル、POEモノオレート、POEジステアレート等のPOE脂肪酸エステル、POEラウリルエーテル、POEステアリルエーテル等のPOEアルキルエーテル、POE・POP水添ラノリン等のPOE・POPアルキルエーテル、硬化ひまし油誘導体、グリセリンアルキルエーテル、アルカノールアミド、ショ糖脂肪酸エステル、デキストリン脂肪酸エステル、でんぷん脂肪酸エステル、ヒドロキシステアリン酸等のノニオン系界面活性剤、その他レシチン等のリン脂質類、トレハロースリピド等の糖脂質類、パーフルオロアルキルリン酸塩、パーフルオロアルキルスルホン酸塩、パーフルオロアルキルカルボン酸塩等のフッ素系界面活性剤等、アクリル酸メタクリル酸アルキル共重合体、ベントナイト、スメクタイト、カオリン等の天然又は合成の粘土鉱物、有機アミンカチオン変性ベントナイト等の有機変性粘土鉱物、アエロゾル等を挙げることができる。 For example, alkyl ether sulfates such as POE lauryl sulfate triethanolamine, alkylbenzene sulfonates such as sodium dodecylbenzenesulfonate, higher alkyl sulfates such as sodium lauryl sulfate and potassium lauryl sulfate, N-acyl sarcosine acid, N- Higher fatty acid amide sulfonates such as sodium myristoyl-N-methyltaurine, higher fatty acid ester sulfates such as hydrogenated coconut oil fatty acid sodium glycerol sulfate, higher fatty acid ester sulfonates, higher fatty acid alkylolamide sulfates, fatty acid soaps , Sulfosuccinate, secondary alcohol sulfate, POE alkyl ether carboxylic acid, POE alkyl allyl ether carboxylate, α-olefin sulfonate, lauroyl mono Anionic surfactants such as sodium tanolamide succinate, N-palmitoyl aspartate diethanolamine, sodium caseinate, alkyltrimethylammonium salts such as stearyltrimethylammonium chloride, alkylpyridinium salts such as distearyldimethylammonium dialkyldimethylammonium chloride, alkyl Quaternary ammonium salt, alkylamine salt, alkyldimethylbenzylammonium salt, alkylisoquinolinium salt, dialkyl morpholinium salt, POE alkylamine, polyamine fatty acid derivative, amyl alcohol fatty acid derivative, benzalkonium chloride, benzethonium chloride, etc. Cationic surfactant, 2-cocoyl-2-imidazolinium hydroxide-1-carboxyethyloxy disodium Imidazoline-based amphoteric surfactants such as salts, betaine-based amphoteric surfactants such as alkylbetaine, amidebetaine, and lauryldimethylaminoacetic acid betaine, glycerin fatty acid esters such as glyceryl sesquioleate and glyceryl monostearate, hexaglyceryl polyricinoleate Polyglycerin fatty acid esters such as diglyceryl monostearate and decaglyceryl dekaoleate, sorbitan fatty acid esters such as sorbitan monooleate and sorbitan sesquioleate, propylene glycol fatty acid esters such as propylene glycol monostearate, POE sorbitan monooleate, etc. POE glycerin fatty acid ester such as POE sorbitan fatty acid ester, POE glycerin triisostearate, POE monooleate, POE dis POE fatty acid esters such as allate, POE alkyl ethers such as POE lauryl ether and POE stearyl ether, POE POP alkyl ethers such as POE / POP hydrogenated lanolin, hardened castor oil derivatives, glycerin alkyl ethers, alkanolamides, sucrose fatty acid esters, Dextrin fatty acid esters, starch fatty acid esters, nonionic surfactants such as hydroxystearic acid, phospholipids such as lecithin, glycolipids such as trehalose lipid, perfluoroalkyl phosphate, perfluoroalkyl sulfonate, Fluorine surfactants such as fluoroalkyl carboxylates, etc., alkyl methacrylate methacrylate copolymers, natural or synthetic clay minerals such as bentonite, smectite and kaolin, organic amine cuticles Organically-modified clay minerals such as down-modified bentonite, can be exemplified aerosol or the like.
本発明における有機化合物被覆粉体を分散媒に混練又は混合分散させる方法は、公知の方法を採用すればよく特に限定されない。例えば、ニーダー混練、ヘンシェル混練、ロール混練、エクストルーダー混練等の混練混合機、プロペラミキサー、ハイスピードミキサー、ディゾルバー、ホモジナイザー、アルテマイザー、湿式ジェットミル、コロイドミル、マスコロイダー、ビーズミル、サンドミル等の湿式混合分散機を使用して分散体を製造することができる。 The method for kneading or mixing and dispersing the organic compound-coated powder in the dispersion medium in the present invention is not particularly limited as long as a known method is adopted. For example, kneading mixers such as kneader kneading, Henschel kneading, roll kneading, extruder kneading, propeller mixers, high speed mixers, dissolvers, homogenizers, artemizers, wet jet mills, colloid mills, mass colloiders, bead mills, sand mills, etc. A dispersion can be produced using a mixing and dispersing machine.
また、前記の有機化合物被覆粉体を配合して化粧料としたり、前記の分散体を用いて液体化粧料としたりしてもよい。例えば、パウダーファンデーション、リキッドファンデーション、油性ファンデーション、スティックファンデーション、プレストパウダー、フェイスパウダー、口紅、リップグロス、頬紅、アイシャドウ、アイブロウ、アイライナー、マスカラ、水性ネイルエナメル、油性ネイルエナメル、乳化型ネイルエナメル、エナメルトップコート、エナメルベースコート等の仕上用化粧品、エモリエントクリーム、コールドクリーム、美白クリーム、乳液、化粧水、美容液、カーマインローション、液状洗顔料、洗顔フォーム、洗顔クリーム、洗顔パウダー、メイククレンジング、ボディグロス等の皮膚用化粧品、ヘアーグロス、ヘアクリーム、ヘアーシャンプー、ヘアリンス、ヘアカラー、ヘアブラッシング剤等の頭髪用化粧品、その他として日焼け止め又は日焼け用クリームや乳液、石鹸、浴用剤、香水等を挙げることができる。 Further, the organic compound-coated powder may be blended to make a cosmetic, or the dispersion may be used to make a liquid cosmetic. For example, powder foundation, liquid foundation, oil foundation, stick foundation, pressed powder, face powder, lipstick, lip gloss, blusher, eye shadow, eyebrow, eyeliner, mascara, aqueous nail enamel, oily nail enamel, emulsified nail enamel, Finishing cosmetics such as enamel top coat, enamel base coat, emollient cream, cold cream, whitening cream, milky lotion, lotion, essence, carmine lotion, liquid facial cleanser, facial cleansing foam, facial cleansing cream, facial cleansing powder, makeup cleansing, body gloss Cosmetics for skin such as hair gloss, hair cream, hair shampoo, hair rinse, hair color, hair brushing agent, etc. Only stop or sunburn cream or milk, can be given soap, bath agent, perfume and the like.
有機化合物被覆粉体の配合量は、化粧料の形態に応じて適宜配合することができ、例えば、液体化粧料には、1〜20重量%が好ましく、1〜15重量%がより好ましく、1〜10重量%が更に好ましい。本発明の化粧料には、通常配合されるものを用いることができ、例えば、顔料分散剤、油剤、界面活性剤、紫外線吸収剤、防腐剤、酸化防止剤、皮膜形成剤、保湿剤、増粘剤、染料、顔料、香料等を適宜配合することができる。 The blending amount of the organic compound-coated powder can be appropriately blended according to the form of the cosmetic. For example, for liquid cosmetics, 1 to 20% by weight is preferable, 1 to 15% by weight is more preferable, and 1 10 to 10% by weight is more preferable. For the cosmetics of the present invention, those usually blended can be used, for example, pigment dispersants, oils, surfactants, ultraviolet absorbers, preservatives, antioxidants, film forming agents, moisturizers, Adhesives, dyes, pigments, fragrances and the like can be appropriately blended.
本発明の有機化合物被覆粉体、その分散体は、化粧料以外の用途にも好適に用いることができ、プラスチックの添加剤、インク、塗料、トナー(磁性粉、外添剤)、化学繊維、包装材料、電子材料等の各種分野で広く使用される。 The organic compound-coated powder of the present invention and the dispersion thereof can be suitably used for applications other than cosmetics, including plastic additives, inks, paints, toners (magnetic powder, external additives), chemical fibers, Widely used in various fields such as packaging materials and electronic materials.
以下に本発明の実施例を示すが、本発明はこれらに制限されるものではない。 Examples of the present invention are shown below, but the present invention is not limited thereto.
実施例1
微粒子酸化チタン(石原産業社製、TTO−S−3)1000gにメチルハイドロジエンシロキサン−ジメチルシロキサン共重合体(信越化学工業社製、KF−9901)60gを加え、ヘンシェルミキサー(三井鉱山社製、MITSUI HENSCHEL 型式;10)を用いて1800rpm、室温下窒素雰囲気で20分間混合した。次いで、混合物を気流粉砕機(セイシン企業社製、ジェットミル)にて粉砕した(第一の工程)。
次いで、粉砕した粉体を、恒温恒湿機(ヤマト科学社製、Humidic Camber IG400)に入れ、温度40〜90℃、湿度50〜95%、時間1〜4時間の条件で調湿処理を施した(第二の工程)。
次に、調湿処理を施した粉体を恒温恒湿機(ヤマト科学社製、Humidic Camber IG400)に入れ、温度120〜150℃、湿度0%(Dry)、時間1〜2時間で加熱処理を施して(第三の工程)、有機化合物被覆粉体(試料A)を得た。
Example 1
To 1000 g of fine particle titanium oxide (Ishihara Sangyo Co., Ltd., TTO-S-3) is added 60 g of methylhydrosiloxane-dimethylsiloxane copolymer (Shin-Etsu Chemical Co., Ltd., KF-9901), and Henschel mixer (Mitsui Mining Co., Ltd., Using a MITSUI HENSCHEL model; 10), the mixture was mixed at 1800 rpm at room temperature in a nitrogen atmosphere for 20 minutes. Next, the mixture was pulverized with an airflow pulverizer (jet mill manufactured by Seishin Enterprise Co., Ltd.) (first step).
Next, the pulverized powder is put into a constant temperature and humidity machine (Humidic Camber IG400, manufactured by Yamato Kagaku Co., Ltd.), and is subjected to humidity control under conditions of a temperature of 40 to 90 ° C., a humidity of 50 to 95%, and a time of 1 to 4 hours. (Second step).
Next, the moisture-treated powder is placed in a thermo-hygrostat (Humidic Camber IG400, manufactured by Yamato Kagaku Co., Ltd.), and heat-treated at a temperature of 120 to 150 ° C., a humidity of 0% (Dry), and a time of 1 to 2 hours. (Third step) to obtain an organic compound-coated powder (Sample A).
比較例1
実施例1において、第一の工程を行った後、第二の工程を行わないで、第一の工程で得た粉体を用いて第三の工程を行うこと以外は実施例1と同様にして、有機化合物被覆粉体(試料B)を得た。
Comparative Example 1
In Example 1, after performing the first step, the second step is not performed, and the third step is performed using the powder obtained in the first step. Thus, an organic compound-coated powder (Sample B) was obtained.
比較例2
実施例1において、第一の工程を行った後、第二の工程を行い、第三の工程を行わないこと以外は実施例1と同様にして、有機化合物被覆粉体(試料C)を得た。
Comparative Example 2
In Example 1, an organic compound-coated powder (sample C) was obtained in the same manner as in Example 1 except that the first step was performed, the second step was performed, and the third step was not performed. It was.
水素残存量の測定
実施例と比較例の試料A、B、Cそれぞれ4gにエタノール約40mlを添加し、2分間撹拌して、発生した水素を捕集した(捕集量aml)。
次に、前記のエタノール分散液に10%の水酸化ナトリウム水溶液5ml添加した後、3分間撹拌して、発生した水素を捕集した(捕集量bml)。
試料の水素残存量を次式で算出した。
水素残存量(ml)=(b−a)/4
実施例1の試料Aは0.3ml/gであるのに対して、比較例1の試料Bは2.0ml/g、比較例2の試料Cは、1.0ml/gであった。この結果から、本発明の方法で製造した被覆粉体は、水素残存量が少ないことがわかった。
Measurement of residual amount of hydrogen About 40 ml of ethanol was added to 4 g of each of Samples A, B, and C of Examples and Comparative Examples and stirred for 2 minutes to collect the generated hydrogen (collected amount aml).
Next, 5 ml of a 10% aqueous sodium hydroxide solution was added to the ethanol dispersion, followed by stirring for 3 minutes to collect the generated hydrogen (collected amount b ml).
The amount of hydrogen remaining in the sample was calculated by the following formula.
Hydrogen remaining amount (ml) = (ba) / 4
Sample A of Example 1 was 0.3 ml / g, while Sample B of Comparative Example 1 was 2.0 ml / g, and Sample C of Comparative Example 2 was 1.0 ml / g. From this result, it was found that the coating powder produced by the method of the present invention has a small amount of residual hydrogen.
撥水性評価
実施例と比較例の試料A、B、Cそれぞれ0.75g、流動パラフィン15g、純水15g、ガラスビーズ20gをマヨネーズ瓶に入れ、ペイントシェーカーで分散した。試料が流動パラフィンにとどまる時間を目視で観察し、撥水性の優劣とした。
実施例1の試料Aは50分であるのに対して、比較例1の試料Bは15分、比較例2の試料Cは5分であった。この結果から、本発明の方法で製造した被覆粉体は、撥水性に優れていることがわかった。
Evaluation of water repellency Samples A, B and C of Examples and Comparative Examples, 0.75 g, liquid paraffin 15 g, pure water 15 g, and glass beads 20 g were placed in a mayonnaise bottle and dispersed with a paint shaker. The time during which the sample stayed in the liquid paraffin was visually observed to make the water repellency superior or inferior.
Sample A of Example 1 was 50 minutes, while Sample B of Comparative Example 1 was 15 minutes, and Sample C of Comparative Example 2 was 5 minutes. From this result, it was found that the coated powder produced by the method of the present invention was excellent in water repellency.
本発明は、有機化合物を被覆した粉体であって、水素残存量が少なく、油性分散安定性(撥水性)等に優れているため、化粧料、プラスチックの添加剤、インク、塗料、トナー(磁性粉、外添剤)、化学繊維、包装材料、電子材料等の各種分野で広く使用される。 The present invention is a powder coated with an organic compound and has a small amount of residual hydrogen and is excellent in oil dispersion stability (water repellency) and the like. Therefore, cosmetics, plastic additives, inks, paints, toners ( Widely used in various fields such as magnetic powder, external additives), chemical fibers, packaging materials, electronic materials, etc.
Claims (3)
次いで、第一の工程で得られた粉砕物及び/又は混合物を40〜200℃の温度で、かつ、その温度の飽和蒸気圧の80〜95%の条件下で水と接触させる第二の工程、
次いで、第二の工程で得られた粉体を50〜200℃の温度で、かつ、湿度0%の条件下で加熱する第三の工程を含む、有機化合物被覆粉体の製造方法。 A first step of pulverizing and / or mixing at least the powder and the hydrolyzable organic compound;
Then, at a first temperature of the pulverized product obtained in step and / or a mixture 40 to 200 ° C., and a second step of contacting with 80% to 95% under conditions of saturated vapor pressure at that temperature and water ,
Next, a method for producing an organic compound-coated powder, comprising a third step of heating the powder obtained in the second step at a temperature of 50 to 200 ° C. and a humidity of 0%.
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