JP2018162400A - Pigment powder surface treatment method - Google Patents
Pigment powder surface treatment method Download PDFInfo
- Publication number
- JP2018162400A JP2018162400A JP2017061012A JP2017061012A JP2018162400A JP 2018162400 A JP2018162400 A JP 2018162400A JP 2017061012 A JP2017061012 A JP 2017061012A JP 2017061012 A JP2017061012 A JP 2017061012A JP 2018162400 A JP2018162400 A JP 2018162400A
- Authority
- JP
- Japan
- Prior art keywords
- powder
- pigment powder
- surface treatment
- pigment
- organic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000843 powder Substances 0.000 title claims abstract description 62
- 239000000049 pigment Substances 0.000 title claims abstract description 47
- 238000004381 surface treatment Methods 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 20
- -1 organic acid compounds Chemical class 0.000 claims abstract description 34
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 230000002378 acidificating effect Effects 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 claims description 13
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 claims description 13
- 229940114124 ferulic acid Drugs 0.000 claims description 13
- 235000001785 ferulic acid Nutrition 0.000 claims description 13
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims description 13
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 230000000052 comparative effect Effects 0.000 abstract description 9
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- 239000000243 solution Substances 0.000 abstract description 2
- 238000001179 sorption measurement Methods 0.000 abstract 1
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- 239000002537 cosmetic Substances 0.000 description 6
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- 239000003125 aqueous solvent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 229910052582 BN Inorganic materials 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- 150000004665 fatty acids Chemical class 0.000 description 2
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- 150000007529 inorganic bases Chemical class 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
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
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- 239000000344 soap Substances 0.000 description 2
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- GYDYJUYZBRGMCC-INIZCTEOSA-N (2s)-2-amino-6-(dodecanoylamino)hexanoic acid Chemical compound CCCCCCCCCCCC(=O)NCCCC[C@H](N)C(O)=O GYDYJUYZBRGMCC-INIZCTEOSA-N 0.000 description 1
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- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
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- YGANSGVIUGARFR-UHFFFAOYSA-N dipotassium dioxosilane oxo(oxoalumanyloxy)alumane oxygen(2-) Chemical compound [O--].[K+].[K+].O=[Si]=O.O=[Al]O[Al]=O YGANSGVIUGARFR-UHFFFAOYSA-N 0.000 description 1
- VPWFPZBFBFHIIL-UHFFFAOYSA-L disodium 4-[(4-methyl-2-sulfophenyl)diazenyl]-3-oxidonaphthalene-2-carboxylate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 VPWFPZBFBFHIIL-UHFFFAOYSA-L 0.000 description 1
- OOYIOIOOWUGAHD-UHFFFAOYSA-L disodium;2',4',5',7'-tetrabromo-4,5,6,7-tetrachloro-3-oxospiro[2-benzofuran-1,9'-xanthene]-3',6'-diolate Chemical compound [Na+].[Na+].O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(Br)=C([O-])C(Br)=C1OC1=C(Br)C([O-])=C(Br)C=C21 OOYIOIOOWUGAHD-UHFFFAOYSA-L 0.000 description 1
- LEHZBQJZYMFYMK-UHFFFAOYSA-L disodium;hexadecyl phosphate Chemical compound [Na+].[Na+].CCCCCCCCCCCCCCCCOP([O-])([O-])=O LEHZBQJZYMFYMK-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 235000012732 erythrosine Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000001056 green pigment Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 1
- 229910000271 hectorite Inorganic materials 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000014413 iron hydroxide Nutrition 0.000 description 1
- WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 description 1
- JCDAAXRCMMPNBO-UHFFFAOYSA-N iron(3+);oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Ti+4].[Ti+4].[Fe+3].[Fe+3] JCDAAXRCMMPNBO-UHFFFAOYSA-N 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229940105112 magnesium myristate Drugs 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- DMRBHZWQMKSQGR-UHFFFAOYSA-L magnesium;tetradecanoate Chemical compound [Mg+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O DMRBHZWQMKSQGR-UHFFFAOYSA-L 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229910052627 muscovite Inorganic materials 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 239000000978 natural dye Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229910052628 phlogopite Inorganic materials 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- KXXXUIKPSVVSAW-UHFFFAOYSA-K pyranine Chemical compound [Na+].[Na+].[Na+].C1=C2C(O)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 KXXXUIKPSVVSAW-UHFFFAOYSA-K 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- NCTHNHPAQAVBEB-WGCWOXMQSA-M sodium ferulate Chemical compound [Na+].COC1=CC(\C=C\C([O-])=O)=CC=C1O NCTHNHPAQAVBEB-WGCWOXMQSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910052917 strontium silicate Inorganic materials 0.000 description 1
- QSQXISIULMTHLV-UHFFFAOYSA-N strontium;dioxido(oxo)silane Chemical compound [Sr+2].[O-][Si]([O-])=O QSQXISIULMTHLV-UHFFFAOYSA-N 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical class [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229940105125 zinc myristate Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229940057977 zinc stearate Drugs 0.000 description 1
- KUPGJMJHAFGISS-UHFFFAOYSA-L zinc;hexadecyl phosphate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCOP([O-])([O-])=O KUPGJMJHAFGISS-UHFFFAOYSA-L 0.000 description 1
- GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Images
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- Cosmetics (AREA)
- Oxygen, Ozone, And Oxides In General (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
Description
本発明は、溶剤に難溶である有機酸化合物を顔料粉体に表面処理する方法に関し、例えば、ファンデーション、アイシャドウ、ほほ紅等のメイクアップ化粧料、あるいはサンスクリーン化粧料に配合される顔料粉体の表面処理方法に関するものである。 The present invention relates to a method for surface-treating a pigment powder with an organic acid compound that is hardly soluble in a solvent, for example, a pigment blended in makeup cosmetics such as foundations, eye shadows, blushers, or sunscreen cosmetics. The present invention relates to a powder surface treatment method.
従来、脂肪酸のような固体状の低分子有機酸化合物を表面処理する方法としては、１）直接化合物と顔料粉体とを、ボールミルまたは、サンドミルのような機械を用いて混合し、表面処理を行う、メカノケミカル的な方法、あるいは、２）適当な溶剤に表面処理剤となる化合物を溶解または懸濁し、顔料粉体と混合した後に溶剤を除去し必要に応じて粉砕を行う方法が知られている（例えば、特許文献１，２参照）。 Conventionally, as a method for surface treatment of a solid low molecular weight organic acid compound such as a fatty acid, 1) the compound and pigment powder are directly mixed using a machine such as a ball mill or a sand mill, and the surface treatment is performed. A mechanochemical method is performed, or 2) a method in which a compound as a surface treatment agent is dissolved or suspended in an appropriate solvent, mixed with pigment powder, the solvent is removed, and pulverization is performed as necessary. (For example, see Patent Documents 1 and 2).
しかしながら、上記処理方法１）では、メカノケミカル的な処理ゆえに、顔料表面に均一に化合物を処理することが困難であり、上記処理方法２）では、溶剤に難溶である有機酸化合物を用いた場合には、均一な処理が困難であり、また、顔料粉体に対して一定の配合量以上処理できないという問題点があった。 However, in the above treatment method 1), it is difficult to treat the compound uniformly on the pigment surface due to the mechanochemical treatment. In the above treatment method 2), an organic acid compound that is hardly soluble in a solvent is used. In some cases, uniform processing is difficult, and the pigment powder cannot be processed beyond a certain blending amount.
本発明は、前述のような問題点に鑑みてなされたもので、従来方法よりも、多くの難溶性有機酸化合物を均一に顔料表面に付着させることのできる顔料粉体の表面処理方法を提供することを目的とするものである。 The present invention has been made in view of the above-mentioned problems, and provides a surface treatment method for pigment powder that can uniformly adhere more hardly soluble organic acid compounds to the pigment surface than conventional methods. It is intended to do.
本発明者らは、有機酸化合物を塩基性水溶媒中に塩として溶解させ、そこへ顔料粉体を添加した後に、酸性条件にすることで有機酸化合物を顔料粉体の表面に析出させ、反応終了後、顔料粉体と溶媒とを分離し乾燥させることで、従来の方法よりも均一に被覆処理できることを見出し、本発明を完成するに至ったものである。 The present inventors dissolved the organic acid compound as a salt in a basic aqueous solvent, and after adding the pigment powder thereto, the organic acid compound was precipitated on the surface of the pigment powder under acidic conditions, After completion of the reaction, the pigment powder and the solvent were separated and dried, and it was found that the coating treatment can be performed more uniformly than the conventional method, and the present invention has been completed.
要するに、前記目的を達成するために、本発明による顔料粉体の表面処理方法は、
分子構造中にカルボキシ基を有する水難溶性有機酸化合物を塩基性条件下で塩として水に溶解させた水溶液中に顔料粉体を混合分散し、該水溶液を酸性にすることにより、前記水難溶性有機酸化合物を前記顔料粉体の表面に析出させて表面処理することを特徴とするものである（第１発明）。
In short, in order to achieve the above object, the surface treatment method of the pigment powder according to the present invention includes:
A pigment powder is mixed and dispersed in an aqueous solution in which a poorly water-soluble organic acid compound having a carboxy group in the molecular structure is dissolved in water as a salt under basic conditions, and the aqueous solution is acidified, whereby the poorly water-soluble organic compound is obtained. The acid compound is precipitated on the surface of the pigment powder and surface-treated (first invention).
本発明において、塩基性条件がｐＨ=９〜１４であり、酸性条件がｐＨ＝１〜５であるのが好ましい（第２発明）。 In the present invention, the basic condition is preferably pH = 9 to 14, and the acidic condition is preferably pH = 1 to 5 (second invention).
本発明において、前記水難溶性有機酸化合物はフェルラ酸であるのが好ましい（第３発明）。 In the present invention, the poorly water-soluble organic acid compound is preferably ferulic acid (third invention).
本発明の顔料粉体の表面処理方法によれば、水難溶性有機酸化合物を塩基性条件下において塩として水に溶解させ、この水難溶性有機酸化合物が溶解した水溶液中に顔料粉体を混合分散させた後、該水溶液を酸性にすることで水難溶性有機酸化合物を顔料粉体の表面に析出させて表面処理するようにされているので、従来方法よりも、多くの難溶性有機酸化合物を均一に顔料表面に付着させることができる。 According to the surface treatment method of pigment powder of the present invention, a poorly water-soluble organic acid compound is dissolved in water as a salt under basic conditions, and the pigment powder is mixed and dispersed in an aqueous solution in which the poorly water-soluble organic acid compound is dissolved. Then, the aqueous solution is acidified so that the poorly water-soluble organic acid compound is deposited on the surface of the pigment powder for surface treatment. It can be uniformly attached to the pigment surface.
次に、本発明による顔料粉体の表面処理方法の具体的な実施の形態について説明する。 Next, a specific embodiment of the pigment powder surface treatment method according to the present invention will be described.
本発明で用いられる分子構造中にカルボキシ基を有し、常温で固体状かつ水に難溶な有機酸化合物の例を示せば、カプリル酸、パルミチン酸、ステアリン酸等の飽和脂肪酸、ケイヒ酸、フェルラ酸等の不溶性のカルボン酸等が挙げられる。中でもフェルラ酸はこれまで化粧料に用いられた実績もあり、油脂類の抗酸化作用、抗菌作用、紫外線吸収作用などを有する有用な物質である。 Examples of organic acid compounds that have a carboxy group in the molecular structure used in the present invention and are solid at room temperature and hardly soluble in water include saturated fatty acids such as caprylic acid, palmitic acid, stearic acid, cinnamic acid, Examples include insoluble carboxylic acids such as ferulic acid. Among them, ferulic acid has been used in cosmetics so far, and is a useful substance having the antioxidant action, antibacterial action, ultraviolet absorption action and the like of fats and oils.
本発明で用いられる水溶媒の重量としては、表面処理される顔料粉体によって異なるが、顔料粉体に対して５倍から２０倍の範囲であることが適当である。水溶媒量が５倍未満の場合では、攪拌可能なスラリーを得ることができず、また２０倍超の場合では、有機酸化合物の析出まで時間がかかってしまい、生産性が低下してしまう。 The weight of the water solvent used in the present invention varies depending on the pigment powder to be surface-treated, but is suitably in the range of 5 to 20 times that of the pigment powder. When the amount of the aqueous solvent is less than 5 times, a stirrable slurry cannot be obtained, and when it is more than 20 times, it takes time until the organic acid compound is precipitated, and the productivity is lowered.
本発明では、有機酸化合物を塩基性水溶媒中に塩として溶解させるが、この時のｐＨとしては、ｐＨ＝９から１５の範囲である必要があり、より好ましくはｐＨ＝１０から１３の間である。 In the present invention, the organic acid compound is dissolved as a salt in a basic aqueous solvent. At this time, the pH needs to be in the range of pH = 9 to 15, more preferably between pH = 10 and 13. It is.
その際用いられる塩基の種類としては、無機塩基、有機塩基が挙げられる。無機塩基としては、ＭｇやＣａ等の多価イオンを含む物を用いた場合には高級脂肪酸等の有機酸化合物と金属セッケンを形成してしまう可能性があるため、ＮａまたはＫの一価のものが好ましく、例えば、水酸化ナトリウム、炭酸ナトリウム、炭酸水素ナトリウム、水酸化カリウム、炭酸カリウム、炭酸水素カリウム等があげられるが、水酸化ナトリウム、炭酸ナトリウムの使用が好適である。有機塩基としては、例えば、アンモニア、トリエチルアミン、トリエタノールアミン等が挙げられるが、アンモニアが好適である。 Examples of the base used at that time include inorganic bases and organic bases. As an inorganic base, when a substance containing a multivalent ion such as Mg or Ca is used, it may form a metal soap with an organic acid compound such as a higher fatty acid. Examples thereof include sodium hydroxide, sodium carbonate, sodium hydrogen carbonate, potassium hydroxide, potassium carbonate, potassium hydrogen carbonate and the like, and the use of sodium hydroxide and sodium carbonate is preferable. Examples of the organic base include ammonia, triethylamine, triethanolamine and the like, and ammonia is preferable.
本発明では、塩基性条件下溶解させた有機酸化合物を酸性にすることで、顔料表面への被覆処理を行うが、この時のｐＨとしては、ｐＨ＝１から５の範囲であることが必要であり、より好ましくはｐＨ＝２から４の範囲である。 In the present invention, the organic acid compound dissolved under basic conditions is acidified to perform coating treatment on the pigment surface. At this time, the pH needs to be in the range of pH = 1 to 5. More preferably, the pH is in the range of 2 to 4.
その際用いられる酸の種類としては、無機酸、有機酸が挙げられる。無機酸としては例えば、塩酸、硝酸、硫酸、ホウ酸、リン酸等が挙げられるが、汎用性が高い、塩酸、硫酸が好適である。有機酸としては、酢酸、クエン酸、シュウ酸、乳酸等が挙げられる。 Examples of the acid used at that time include inorganic acids and organic acids. Examples of the inorganic acid include hydrochloric acid, nitric acid, sulfuric acid, boric acid, phosphoric acid, and the like, and hydrochloric acid and sulfuric acid having high versatility are preferable. Examples of the organic acid include acetic acid, citric acid, oxalic acid, and lactic acid.
本発明に用いられる化粧料用顔料としては、例えば、無機顔料、有機顔料および樹脂粉体顔料等がある。 Examples of cosmetic pigments used in the present invention include inorganic pigments, organic pigments, and resin powder pigments.
無機粉体としては、例えば、酸化チタン、酸化ジルコニウム、酸化亜鉛、酸化セリウム、酸化マグネシウム、硫酸バリウム、硫酸カルシウム、硫酸マグネシウム、炭酸カルシウム、炭酸マグネシウム、タルク、マイカ、カオリン、セリサイト、白雲母、合成雲母、金雲母、紅雲母、黒雲母、リチア雲母、ケイ酸、無水ケイ酸、ケイ酸アルミニウム、ケイ酸マグネシウム、ケイ酸アルミニウムマグネシウム、ケイ酸カルシウム、ケイ酸バリウム、ケイ酸ストロンチウム、タングステン酸金属塩、ヒドロキシアパタイト、バーミキュライト、ハイジライト、ベントナイト、モンモリロナイト、ヘクトライト、ゼオライト、セラミックスパウダー、第二リン酸カルシウム、アルミナ、水酸化アルミニウム、窒化ホウ素、窒化ボロン、シリカ等が挙げられる。 Examples of the inorganic powder include titanium oxide, zirconium oxide, zinc oxide, cerium oxide, magnesium oxide, barium sulfate, calcium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, talc, mica, kaolin, sericite, muscovite, Synthetic mica, phlogopite, saucite, biotite, lithia mica, silicic acid, anhydrous silicic acid, aluminum silicate, magnesium silicate, magnesium aluminum silicate, calcium silicate, barium silicate, strontium silicate, metal tungstate Salt, hydroxyapatite, vermiculite, hydrite, bentonite, montmorillonite, hectorite, zeolite, ceramic powder, dicalcium phosphate, alumina, aluminum hydroxide, boron nitride, boron nitride, silica, etc. It is.
有機粉体としては、例えば、ポリアミドパウダー、ポリエステルパウダー、ポリエチレンパウダー、ポリプロピレンパウダー、ポリスチレンパウダー、ポリウレタンパウダー、ベンゾグアナミンパウダー、ポリメチルベンゾグアナミンパウダー、ポリテトラフルオロエチレンパウダー、ポリメチルメタクリレートパウダー、セルロース、シルクパウダー、ナイロンパウダー、１２ナイロン、６ナイロン、アクリルパウダー、アクリルエラストマー、スチレン・アクリル酸共重合体、ジビニルベンゼン・スチレン共重合体、ビニル樹脂、尿素樹脂、フェノール樹脂、フッ素樹脂、ケイ素樹脂、アクリル樹脂、メラミン樹脂、エポキシ樹脂、ポリカーボネイト樹脂、微結晶繊維粉体、デンプン末、ラウロイルリジン等が挙げられる。 Examples of organic powders include polyamide powder, polyester powder, polyethylene powder, polypropylene powder, polystyrene powder, polyurethane powder, benzoguanamine powder, polymethylbenzoguanamine powder, polytetrafluoroethylene powder, polymethyl methacrylate powder, cellulose, silk powder, Nylon powder, 12 nylon, 6 nylon, acrylic powder, acrylic elastomer, styrene / acrylic acid copolymer, divinylbenzene / styrene copolymer, vinyl resin, urea resin, phenol resin, fluororesin, silicon resin, acrylic resin, melamine Resins, epoxy resins, polycarbonate resins, microcrystalline fiber powder, starch powder, lauroyl lysine and the like can be mentioned.
界面活性剤金属塩粉体（金属石鹸）としては、例えば、ステアリン酸亜鉛、ステアリン酸アルミニウム、ステアリン酸カルシウム、ステアリン酸マグネシウム、ミリスチン酸亜鉛、ミリスチン酸マグネシウム、セチルリン酸亜鉛、セチルリン酸カルシウム、セチルリン酸亜鉛ナトリウム等が挙げられる。 As the surfactant metal salt powder (metal soap), for example, zinc stearate, aluminum stearate, calcium stearate, magnesium stearate, zinc myristate, magnesium myristate, zinc cetyl phosphate, calcium cetyl phosphate, sodium cetyl phosphate Etc.
有色顔料としては、例えば、酸化鉄、水酸化鉄、チタン酸鉄の無機赤色顔料、γ−酸化鉄等の無機褐色系顔料、黄酸化鉄、黄土等の無機黄色系顔料、黒酸化鉄、カーボンブラック等の無機黒色顔料、マンガンバイオレット、コバルトバイオレット等の無機紫色顔料、水酸化クロム、酸化クロム、酸化コバルト、チタン酸コバルト等の無機緑色顔料、紺青、群青等の無機青色系顔料、微粒子酸化チタン、微粒子酸化セリウム、微粒子酸化亜鉛等の微粒子粉体、タール系色素をレーキ化したもの、天然色素をレーキ化したもの、及びこれらの粉体を複合化した合成樹脂粉体等が挙げられる。 Examples of colored pigments include inorganic red pigments such as iron oxide, iron hydroxide, and iron titanate, inorganic brown pigments such as γ-iron oxide, inorganic yellow pigments such as yellow iron oxide and loess, black iron oxide, carbon Inorganic black pigments such as black, inorganic purple pigments such as manganese violet and cobalt violet, inorganic green pigments such as chromium hydroxide, chromium oxide, cobalt oxide and cobalt titanate, inorganic blue pigments such as bitumen and ultramarine blue, fine particle titanium oxide , Fine particle powders such as fine particle cerium oxide and fine particle zinc oxide, those obtained by lacquering tar dyes, those obtained by lacquering natural dyes, and synthetic resin powders obtained by combining these powders.
パール顔料としては、例えば、酸化チタン被覆雲母、酸化チタン被覆マイカ、オキシ塩化ビスマス、酸化チタン被覆オキシ塩化ビスマス、酸化チタン被覆タルク、魚鱗箔、酸化チタン被覆着色雲母等；金属粉末顔料としては、アルミニウムパウダー、カッパーパウダー、ステンレスパウダー等から選ばれる粉体が挙げられる。 Examples of the pearl pigment include titanium oxide-coated mica, titanium oxide-coated mica, bismuth oxychloride, titanium oxide-coated bismuth oxychloride, titanium oxide-coated talc, fish scale foil, titanium oxide-coated colored mica, and the metal powder pigment includes aluminum. Examples thereof include powders selected from powder, copper powder, stainless steel powder and the like.
また、タール色素としては、例えば、赤色３号、赤色１０４号、赤色１０６号、赤色２０１号、赤色２０２号、赤色２０４号、赤色２０５号、赤色２２０号、赤色２２６号、赤色２２７号、赤色２２８号、赤色２３０号、赤色４０１号、赤色５０５号、黄色４号、黄色５号、黄色２０２号、黄色２０３号、黄色２０４号、黄色４０１号、青色１号、青色２号、青色２０１号、青色４０４号、緑色３号、緑色２０１号、緑色２０４号、緑色２０５号、橙色２０１号、橙色２０３号、橙色２０４号、橙色２０６号、橙色２０７号等；天然色素としては、カルミン酸、ラッカイン酸、カルサミン、ブラジリン、クロシン等から選ばれる顔料が挙げられる。 Examples of the tar pigment include red No. 3, red 104, red 106, red 201, red 202, red 204, red 205, red 220, red 226, red 227, red 228, Red 230, Red 401, Red 505, Yellow 4, Yellow 5, Yellow 202, Yellow 203, Yellow 204, Yellow 401, Blue 1, Blue 2, Blue 201 , Blue 404, green 3, green 201, green 204, green 205, orange 201, orange 203, orange 204, orange 206, orange 207, etc .; natural pigments include carminic acid, Examples thereof include pigments selected from lacaic acid, calsamine, bradylin, crocin and the like.
ここで、有機酸化合物の顔料粉体への表面被覆処理量は、顔料粉体によって異なるが、０．０５〜３０質量％の範囲であり、好ましくは、０．１〜２０質量％の範囲である。０．０５質量％未満では、十分な撥水性や紫外線吸収能等の目的とする機能を得ることができず、３０質量％超では、有機酸化合物の過剰物が、表面被覆処理されずに、単体として残り、処理顔料粉体の機能性や流動性に問題が生じる。 Here, the surface coating amount of the organic acid compound to the pigment powder varies depending on the pigment powder, but is in the range of 0.05 to 30% by mass, preferably in the range of 0.1 to 20% by mass. is there. If it is less than 0.05% by mass, the desired functions such as sufficient water repellency and ultraviolet absorbing ability cannot be obtained, and if it exceeds 30% by mass, an excess of the organic acid compound is not subjected to surface coating treatment. It remains as a simple substance, causing problems in the functionality and fluidity of the treated pigment powder.
次に、本発明の代表的な実施例について図面を参照しつつ説明する。なお、これらの実施例は本発明の技術的範囲を限定するものではない。 Next, typical embodiments of the present invention will be described with reference to the drawings. These examples do not limit the technical scope of the present invention.
（実施例１）
水２００ｇにフェルラ酸２ｇを添加し、３０分間攪拌懸濁させた。次にｐＨ＝１２になるまで５％水酸化ナトリウム水溶液を滴下し、懸濁液が完全に透明になったことを確認し、黄透色のフェルラ酸ナトリウム水溶液を得た。そこへ、板状セルロース粉体を２０ｇ添加し、１０分間分散させた後に、５％塩酸をｐＨ＝３になるまで添加し、フェルラ酸を顔料粉体表面に析出させた。さらに、ろ過、乾燥、粉砕を行うことで、フェルラ酸によって表面処理された板状セルロース粉体を得た。
Example 1
2 g of ferulic acid was added to 200 g of water and suspended by stirring for 30 minutes. Next, 5% aqueous sodium hydroxide solution was added dropwise until pH = 12, confirming that the suspension was completely transparent, and a yellow translucent sodium ferulate aqueous solution was obtained. Thereto, 20 g of plate-like cellulose powder was added and dispersed for 10 minutes, and then 5% hydrochloric acid was added until pH = 3 to deposit ferulic acid on the pigment powder surface. Furthermore, plate-like cellulose powder surface-treated with ferulic acid was obtained by performing filtration, drying, and pulverization.
（実施例２）
実施例１において、板状セルロース粉体をセリサイトに変更した以外は同様にして、フェルラ酸によって処理されたセリサイトを得た。
(Example 2)
A sericite treated with ferulic acid was obtained in the same manner as in Example 1, except that the plate-like cellulose powder was changed to sericite.
（比較例１）
フェルラ酸２ｇと板状セルロース粉体２０ｇをボールミルに投入、攪拌混合し、メカノケミカル的にフェルラ酸が表面処理された板状セルロース粉体を得た。
(Comparative Example 1)
2 g of ferulic acid and 20 g of plate-like cellulose powder were placed in a ball mill and mixed by stirring to obtain a plate-like cellulose powder having a mechanochemical surface treatment with ferulic acid.
（比較例２）
比較例１において板状セルロース粉体をセリサイトに変更した以外同様にして、メカノケミカル的にフェルラ酸が表面処理されたセリサイトを得た。
(Comparative Example 2)
In the same manner as in Comparative Example 1, except that the plate-like cellulose powder was changed to sericite, sericite having a mechanochemical surface-treated ferulic acid was obtained.
（評価方法）
実施例、比較例で得られたフェルラ酸処理粉体を４倍量のジメチコンオイル中に分散し、得られたペースト状のサンプルの透過率を測定し、粉体のＵＶ吸収能を比較した。フェルラ酸は優れたＵＶ吸収能を有しており、均一に表面処理がなされた試験体の方がより優れたＵＶ吸収を示すと考えられる。
(Evaluation method)
The ferulic acid-treated powders obtained in Examples and Comparative Examples were dispersed in 4 times the amount of dimethicone oil, the transmittance of the obtained paste-like samples was measured, and the UV absorption ability of the powders was compared. Ferulic acid has an excellent UV-absorbing ability, and it is considered that a specimen subjected to uniform surface treatment exhibits better UV absorption.
図１（ａ）および（ｂ）のグラフに示される実施例１，２と比較例１，２の比較から、本発明の表面処理方法で処理した実施例１，２のＵＶ吸収能がメカノケミカル的に表面処理した比較例１，２よりも優れることが明らかである。 From the comparison of Examples 1 and 2 and Comparative Examples 1 and 2 shown in the graphs of FIGS. 1A and 1B, the UV absorption ability of Examples 1 and 2 treated by the surface treatment method of the present invention is mechanochemical. It is clear that it is superior to Comparative Examples 1 and 2 subjected to surface treatment.
本発明の顔料粉体の表面処理方法にて難溶性有機酸化合物にて表面処理された顔料粉体は、ファンデーション、アイシャドウ、ほほ紅等のメイクアップ化粧料、あるいはサンスクリーン化粧料に配合して好適であり、産業上の利用可能性が大である。
The pigment powder surface-treated with a sparingly soluble organic acid compound by the pigment powder surface treatment method of the present invention is incorporated into makeup cosmetics such as foundations, eye shadows, blushers, or sunscreen cosmetics. The industrial applicability is great.
Claims (3)
The surface treatment method for a pigment powder according to claim 1 or 2, wherein the poorly water-soluble organic acid compound is ferulic acid.
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