JPH04149233A - Esterification product and cosmetic containing the same blended therein - Google Patents
Esterification product and cosmetic containing the same blended thereinInfo
- Publication number
- JPH04149233A JPH04149233A JP27424390A JP27424390A JPH04149233A JP H04149233 A JPH04149233 A JP H04149233A JP 27424390 A JP27424390 A JP 27424390A JP 27424390 A JP27424390 A JP 27424390A JP H04149233 A JPH04149233 A JP H04149233A
- Authority
- JP
- Japan
- Prior art keywords
- alcohol
- acid
- product
- esterification reaction
- dibasic 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
- 239000002537 cosmetic Substances 0.000 title claims abstract description 18
- 238000005886 esterification reaction Methods 0.000 title claims abstract description 15
- 230000032050 esterification Effects 0.000 title claims description 9
- 239000002253 acid Substances 0.000 claims abstract description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000003606 oligomerizing effect Effects 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract description 4
- 235000012000 cholesterol Nutrition 0.000 abstract description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 abstract 2
- 125000005313 fatty acid group Chemical group 0.000 abstract 1
- 229920002545 silicone oil Polymers 0.000 description 12
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 150000003376 silicon Chemical class 0.000 description 9
- 239000004205 dimethyl polysiloxane Substances 0.000 description 7
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 7
- -1 polysiloxane Polymers 0.000 description 7
- 239000003205 fragrance Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000006384 oligomerization reaction Methods 0.000 description 5
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 239000003974 emollient agent Substances 0.000 description 4
- 229940057995 liquid paraffin Drugs 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 2
- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- BTZVDPWKGXMQFW-UHFFFAOYSA-N Pentadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCC(O)=O BTZVDPWKGXMQFW-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 210000002615 epidermis Anatomy 0.000 description 2
- 229940075507 glyceryl monostearate Drugs 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- QQHJDPROMQRDLA-UHFFFAOYSA-N hexadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC(O)=O QQHJDPROMQRDLA-UHFFFAOYSA-N 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 2
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- NQDZCRSUOVPTII-UHFFFAOYSA-N 10-methylundecan-1-ol Chemical compound CC(C)CCCCCCCCCO NQDZCRSUOVPTII-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- ZXUOFCUEFQCKKH-UHFFFAOYSA-N 12-methyltridecan-1-ol Chemical compound CC(C)CCCCCCCCCCCO ZXUOFCUEFQCKKH-UHFFFAOYSA-N 0.000 description 1
- FDAZSZUYCOPJED-UHFFFAOYSA-N 13-methyltetradecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCO FDAZSZUYCOPJED-UHFFFAOYSA-N 0.000 description 1
- CFSSWEQYBLCBLH-UHFFFAOYSA-N 14-methylpentadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCO CFSSWEQYBLCBLH-UHFFFAOYSA-N 0.000 description 1
- DUYTZBDODDICEJ-UHFFFAOYSA-N 17-methyloctadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCCO DUYTZBDODDICEJ-UHFFFAOYSA-N 0.000 description 1
- YXHAAEIHLXHTJP-UHFFFAOYSA-N 18-methylnonadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCCCO YXHAAEIHLXHTJP-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 1
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
- JTKHUJNVHQWSAY-UHFFFAOYSA-N 9-methyldecan-1-ol Chemical compound CC(C)CCCCCCCCO JTKHUJNVHQWSAY-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000010919 Copernicia prunifera Nutrition 0.000 description 1
- 244000180278 Copernicia prunifera Species 0.000 description 1
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 244000297627 Senna alata Species 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HGKOWIQVWAQWDS-UHFFFAOYSA-N bis(16-methylheptadecyl) 2-hydroxybutanedioate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CC(O)C(=O)OCCCCCCCCCCCCCCCC(C)C HGKOWIQVWAQWDS-UHFFFAOYSA-N 0.000 description 1
- 239000004204 candelilla wax Substances 0.000 description 1
- 235000013868 candelilla wax Nutrition 0.000 description 1
- 229940073532 candelilla wax Drugs 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003676 hair preparation Substances 0.000 description 1
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 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 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- XGFDHKJUZCCPKQ-UHFFFAOYSA-N n-nonadecyl alcohol Natural products CCCCCCCCCCCCCCCCCCCO XGFDHKJUZCCPKQ-UHFFFAOYSA-N 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
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 229920001558 organosilicon polymer Polymers 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940068065 phytosterols Drugs 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000002328 sterol group Chemical group 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/09—Use of materials for the conductive, e.g. metallic pattern
- H05K1/092—Dispersed materials, e.g. conductive pastes or inks
- H05K1/095—Dispersed materials, e.g. conductive pastes or inks for polymer thick films, i.e. having a permanent organic polymeric binder
Landscapes
- Cosmetics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Silicon Polymers (AREA)
Abstract
Description
【発明の詳細な説明】
（ａｌ 産業上の利用分野
本発明はアルコール変性シリコンと二塩基酸とのオリゴ
マー化物と、アルコールとのエステル化生成物およびこ
れを配合してなる化粧料に係る。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to an esterification product of an oligomerized product of an alcohol-modified silicone and a dibasic acid and an alcohol, and a cosmetic prepared by blending the same.
（ｂｌ 従来の技術
シリコンオイルは粘度安定性、熱酸化安定性、潤滑性、
撥水性、光沢性、防錆・防蝕性、等に１くれ、計器類の
防振油、機械類潤滑油、ガラス名器等の撥水剤、ワック
ス添加剤、消泡剤、化粧Ｍ添加剤等に幅広く応用されて
いる。(bl Conventional technology silicone oil has viscosity stability, thermal oxidation stability, lubricity,
Water repellency, gloss, anti-rust/corrosion properties, etc., anti-vibration oil for instruments, lubricating oil for machinery, water repellent for glass products, wax additives, antifoaming agents, cosmetic M additives It is widely applied to
通常シリコンオイルはジメチルポリシロキサンカー１１
ＪＩであり、その他メチルフェニルポリシロキサン、メ
チルハイＦロジエンボリシロキサン、オクタメチルシク
ロテトラシロキサン、デカメチルシクロペンタシロキサ
ン、ジメチルポリシロキサンポリエチレングリコール共
重合体、ジメチルポリシロキサンポリプロピレングリコ
ール共重合体等が知られているが、近年シランカップリ
ング剤として分子中に２個以上の異なった反応基をもつ
存機ケイ素車量体およびこれらの誘導体、さらにはメチ
ルスチレン変性、オレフィン変性、ポリエーテル変性、
アルコール変性、）、素度性、親水性特殊変性、アミノ
変性、メルカプト変性、エポキシ変性、カルボキシル変
性、高級脂肪酸変性等、各種変性う・リコンオイルがあ
り、これらは信越化学工業株式会社、チッソ株式会社、
トーレ・シリコーン株式会社等から市販されている。Usually silicone oil is dimethylpolysiloxane car 11
JI, and other known products include methylphenylpolysiloxane, methylhigh-F rhodiene polysiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dimethylpolysiloxane polyethylene glycol copolymer, dimethylpolysiloxane polypropylene glycol copolymer, etc. However, in recent years, as silane coupling agents, organic silicon polymers with two or more different reactive groups in the molecule and derivatives thereof, as well as methylstyrene-modified, olefin-modified, polyether-modified,
There are various types of modified cartilage and recon oils such as alcohol-denatured, ), hydrophilic special modification, amino-modification, mercapto-modification, epoxy-modification, carboxyl-modification, and higher fatty acid modification, and these are manufactured by Shin-Etsu Chemical Co., Ltd. and Chisso Corporation. company,
It is commercially available from Toray Silicone Co., Ltd., etc.
このようなシリコンオイルは、化粧品用油剤としても良
く使用されでいるがその主な目的は１Ω水性、非粘着性
、潤滑性等にすぐれる特徴から化粧くずれのしにくいフ
ァンデーション、のびの良いＬ］紅等を得ることにある
。また、近年は、頭髪関係（特に枝モコート）への利用
が増加している。Such silicone oils are often used as cosmetic oils, but their main purpose is to create foundations that do not easily bleed makeup due to their excellent properties such as 1Ω water-based, non-stick, and lubricity properties, and to create makeup that spreads easily. The goal is to obtain red color. In addition, in recent years, its use for hair-related products (particularly branch mocotes) has been increasing.
しかるに化粧料油剤として用いる場合はシリコンオイル
の特性を有し、かつ高粘度を有し八からもべたつきかな
く、さらに他成分との相溶性に優れていることか要求さ
れる。However, when used as a cosmetic oil, it is required to have the characteristics of a silicone oil, have high viscosity, be completely non-sticky, and have excellent compatibility with other ingredients.
しかじ、従来ジメチルポリシロキサン等のシリコンオイ
ルの粘度を高めるには、分子量を増大させることが一般
的であったが、これらの高粘度シリコンオイルはエタノ
ール等の極性溶剤に対する相溶性が非常に悪く、また乳
化系で使用する場合には乳化しにくく、か一つ撥水性は
非常に高いもののべたつき、脂ぎった光沢を有し、使用
目的によっては好ましからぬ物性を示す。さらにジメチ
ルポリシロキサンジオール等の極性の箭いシリコンオイ
ルは、極性溶剤に対する溶解性は非常に高いが逆にワセ
リン、ラノリン、植物油等の溶剤に対する相溶性が非常
に悪い欠点を示す。However, in order to increase the viscosity of silicone oils such as dimethylpolysiloxane, it was common to increase the molecular weight, but these high viscosity silicone oils have very poor compatibility with polar solvents such as ethanol. Also, when used in an emulsifying system, it is difficult to emulsify, and although it has very high water repellency, it has stickiness and a greasy shine, and exhibits physical properties that are undesirable depending on the purpose of use. Furthermore, polar silicone oils such as dimethylpolysiloxane diol have a very high solubility in polar solvents, but have the disadvantage of very poor compatibility with solvents such as vaseline, lanolin, and vegetable oil.
特公平１−２１８３３号公報には、ジメチルポリシロキ
サンジオールと二塩基酸とのエステル化生成物が記載さ
れており、これは上記の欠点を解決せんとするものであ
る。Japanese Patent Publication No. 1-21833 describes an esterification product of dimethylpolysiloxane diol and dibasic acid, which is intended to solve the above-mentioned drawbacks.
（Ｃ１発明が解決しようとする課題
本発明の目的は前記したシリコンオイルの欠点を、特公
平１−２１８３３号公報に記載された方法とは別の手段
により排除し、かつ従来のシリコンオイルでは得られな
い優れた特性を有した新規シリコン系エステル化生成物
およびこれらを使用しまた化粧料を得ることにある。(C1 Problem to be Solved by the Invention) The purpose of the present invention is to eliminate the above-mentioned drawbacks of silicone oil by means different from the method described in Japanese Patent Publication No. 1-21833, and to solve the problems that conventional silicone oils cannot provide. The object of the present invention is to obtain novel silicone-based esterified products having excellent properties never seen before, and cosmetics using these products.
ｆｄ） 課題を解決するための手段
本発明は一般式（１）または（ＩＩ）で示される、アル
コール変性シリコンを二塩基酸でオリゴマー化し７たジ
カルボン酸と、アルコールとのエステル化生成Ｔｈお４
゛び該エステル化生成物を含有してなる化粧ｔ１に係る
。fd) Means for Solving the Problems The present invention is directed to an esterification product of dicarboxylic acid represented by the general formula (1) or (II) obtained by oligomerizing alcohol-modified silicon with a dibasic acid and an alcohol.
and the cosmetic t1 containing the esterified product.
Ｒ，、Ｒ，はアルコールの残基であり、ＲＩ＝Ｒｚまた
はＲ１≠Ｒ２゜
（Ｋは１〜１０の整数、ｎはＯまたは１以上の整数、議
は１〜１８の整数）
上記のアルコール変性シリコンとは、ジメチルポリシロ
キサンの両末端にエーテル基を有し、脂肪酸アルコール
性水酸基を官能基に有するジオールである。このアルコ
ール変性シリコン１モルに対し二塩基酸を２モル反応さ
せることにより、アルコール変成シリコンと二塩基酸の
オリゴマーが生成される。ここで二塩基酸としては飽和
、不飽和、ヒドロキシ、芳香族等いずれの二塩基酸も使
用できるが、油剤、溶剤への相溶性、酸化安定性、安全
性等の面から考え、シュウ酸、マロン酸、コノ＼り酸、
グルタル酸、アジピン酸、ピメリン酸、スペリン酸、ア
ゼライン酸、セバシン酸、ウンデカンジオン酸、ドデカ
ンジオン酸、トリデカンジオン酸、テトラデカンジオン
酸、ペンタデカンジオン酸、ヘキサデカンジオン酸、エ
イコサンジオン酸等の炭素数２０以下の脂肪族飽和二塩
基酸、およびヒドロキシニ塩基酸であるリンゴ酸、酒石
酸が好ましい。R,, R, are residues of alcohol, RI = Rz or R1≠R2゜ (K is an integer of 1 to 10, n is O or an integer of 1 or more, and is an integer of 1 to 18) The modified silicone is a diol having ether groups at both ends of dimethylpolysiloxane and a fatty acid alcoholic hydroxyl group as a functional group. By reacting 2 moles of dibasic acid with 1 mole of alcohol-modified silicon, an oligomer of alcohol-modified silicon and dibasic acid is produced. As the dibasic acid, any dibasic acid such as saturated, unsaturated, hydroxy, aromatic, etc. can be used, but from the viewpoint of compatibility with oils and solvents, oxidation stability, safety, etc., oxalic acid, malonic acid, cono-lyric acid,
Carbon of glutaric acid, adipic acid, pimelic acid, superic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, eicosanedionic acid, etc. Preferred are aliphatic saturated dibasic acids having a number of 20 or less, and malic acid and tartaric acid, which are hydroxy dibasic acids.
このオリゴマー化したジカルボン酸１モルに対し、アル
コールの仕込み比を２モル以上で合成した場合は一般式
（１）のエステル化生成物が合成される。このときアル
コールとして２種以上混合してもかまわない。またこの
両者の仕込み比を１＝１とすれば、一般式（ｎ）で示さ
れるエステル化生成物が合成される。ここでアルコール
としては飽和または不飽和、直鎖または分岐型、芳香族
あるいはステロール類などのアルコールを用い、その種
類としては油剤、溶剤等への相溶性、酸化安定性、安全
性などの面から考えて、ヘプタツール、オクタツール、
ノナノール、デカノール、ウンデカノール、Ｆデカノー
ル、トリデカノール、テトラデカノール、ペンタデカノ
ール、ヘキサデカノール、ヘプタデカノール、オクタデ
カノール、ノナデカノール、エイコサノール、ドコサノ
ール、イソヘプタツール、イソオクタツール、イソノナ
ノール、イソデカノール、イソウンデカノール、イソド
デカノール、イソトリデカノール、イソテトラデカノー
ル、イソペンタデカノール、イソヘキサデカノール、イ
ンヘプタデカノール、イソオクタデカノール、イソノナ
デカノール、イソエイコサノール、イソドコサノールな
どの炭素数２以上２２以下のアルコールまたは、ステロ
ール骨格を有するアルコールとしてはコレステロール、
フィトステロールなどが望ましい。When synthesis is carried out at a charging ratio of 2 moles or more of alcohol to 1 mole of the oligomerized dicarboxylic acid, an esterified product of general formula (1) is synthesized. At this time, two or more kinds of alcohols may be mixed. Further, if the charging ratio of both is set to 1=1, an esterified product represented by the general formula (n) is synthesized. Here, the alcohol used is saturated or unsaturated, linear or branched, aromatic or sterol alcohol, and the type of alcohol is determined based on compatibility with oils, solvents, etc., oxidation stability, safety, etc. Think, heptatool, octatool,
Nonanol, decanol, undecanol, F decanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, eicosanol, docosanol, isoheptatool, isooctatool, isononanol, isodecanol, iso Undecanol, isododecanol, isotridecanol, isotetradecanol, isopentadecanol, isohexadecanol, inheptadecanol, isooctadecanol, isononadecanol, isoeicosanol, isodocosa Alcohols having 2 to 22 carbon atoms such as alcohol, or alcohols having a sterol skeleton include cholesterol,
Phytosterols are preferable.
それぞれ以下に示す合成法により合成し、分離精製する
ことにより、単品として使用することができる。また、
上記エステル化生成物の２種以上の混合品も、従来のシ
リコンオイルの持つ欠点を解決するに何ら支障のないも
のであり、これらもまた使用することができる。Each can be synthesized by the synthesis method shown below, separated and purified, and used as a single product. Also,
Mixtures of two or more of the above-mentioned esterification products can also be used as they have no problem in solving the drawbacks of conventional silicone oils.
エステル化反応は無触媒、または触媒存在下常圧もしく
は減圧下において常法に従って行われる。The esterification reaction is carried out without a catalyst or in the presence of a catalyst under normal pressure or reduced pressure according to a conventional method.
まずアルコール変成シリコンと二塩基酸のエステル化反
応、すなわちオリゴマー化を進める。ここで酸化の低下
がみられなくなったときに反応を一時停止し、そのとき
の酸価に見合うだけのアルコールを新たに添加し、再度
エステル化反応を進める。このとき添加するアルコール
のモル比は適宜調節される。またアルコール変成シリコ
ンと二塩基酸のオリゴマー化度（Ｋ）の低いエステル化
物を合成する際には、アルコール変成シリコンと上記の
アルコールを二塩基酸と同時に仕込み、反応させること
が可能である。しかしながらこのときアルコール変成シ
リコンと二塩基酸のオリゴマー化度（Ｋ）は通常３以下
である。このように反応した粗エステル化物は、エステ
ル化終了後常法に従って脱色剤による脱色、ついで水蒸
気による脱臭精製を行う。First, proceed with the esterification reaction between alcohol-modified silicon and dibasic acid, that is, oligomerization. When no decrease in oxidation is observed, the reaction is temporarily stopped, and an amount of alcohol corresponding to the acid value at that time is newly added, and the esterification reaction is proceeded again. The molar ratio of the alcohol added at this time is adjusted as appropriate. Furthermore, when synthesizing an esterified product of alcohol-modified silicon and a dibasic acid with a low degree of oligomerization (K), it is possible to simultaneously charge the alcohol-modified silicon and the above-mentioned alcohol with the dibasic acid and allow them to react. However, in this case, the degree of oligomerization (K) of the alcohol-modified silicon and the dibasic acid is usually 3 or less. After the completion of esterification, the crude esterified product thus reacted is decolorized using a decolorizing agent and then deodorized and purified using steam according to a conventional method.
得られたエステル化生成物に常用成分、任意成分を適宜
配合して各種化粧料を調製する。即ち従来の油剤、エモ
リエント剤等の全部または一部を本発明のエステル化生
成物に替えて常法により調製される。エステル化生成物
の配合は一部に規定できないが一般に０．１〜３０重量
２である。化粧料の種類は特に制限はなく、頭髪用化粧
品類、洗髪用化粧品類、化粧水類、クリーム乳液類、バ
ック類、ファンデーション類、白粉打粉類、口紅類、層
目頬化粧品類、爪化粧品類、浴用化粧品類、化粧用油類
、洗顔料類、石けん類に適用することができる。Various cosmetics are prepared by appropriately blending commonly used ingredients and optional ingredients with the obtained esterified product. That is, it is prepared by a conventional method by replacing all or part of conventional oil agents, emollients, etc. with the esterified product of the present invention. Although the proportion of the esterified product cannot be specified, it is generally 0.1 to 30% by weight2. There are no particular restrictions on the types of cosmetics, including hair cosmetics, hair washing cosmetics, lotions, cream emulsions, bags, foundations, whitening powders, lipsticks, layered cheek cosmetics, and nail cosmetics. It can be applied to bath cosmetics, cosmetic oils, facial cleansers, and soaps.
（ｅ）実施例
実施例１ エステル化生成物の調製
アルコール変性シリコン（平均分子置駒１０００、粘度
２３ｃｐｓ／２５℃、重合度ｎ＝１０） ３１０ｇとア
ジピン酸１００ｇを撹拌機、温度計、窒素ガス吹込管、
水分離管を備えた１１の四ソロフラスコに仕込み、触媒
として塩化スズを全仕込み量の０．３％、還流溶剤とし
てキジロールを全仕込み量の５χ、−緒に加え、よ（撹
拌し、混合物を１６０〜２５０℃で６時間反応させた。(e) Examples Example 1 Preparation of esterification product 310 g of alcohol-modified silicone (average molecular weight 1000, viscosity 23 cps/25°C, degree of polymerization n = 10) and 100 g of adipic acid were placed in a stirrer, thermometer, and nitrogen gas. blowing pipe,
Charge 11 tetrasol flasks equipped with a water separation tube, add 0.3% of tin chloride as a catalyst and 5% of the total charge of kijirole as a refluxing solvent, stir (stir, and mix well). was reacted at 160 to 250°C for 6 hours.
反応終了後、酸価を測定しく＾Ｖ・９２）この値に見合
うだけの量としてステアリルアルコールを１９０ｇ添加
した。ここで系の温度を１６０〜２５０℃に戻し、よく
撹拌しながらさらに１０時間反応させた。反応終了後、
触媒を濾別し、つぎに活性白土を用いて脱色後、減圧下
にて水蒸気吹き込みによる脱臭を行い目的とする生成物
（試料患１）を得た。以下同様にして二塩基酸ならびに
アルコールの組成を変えた系で反応させ、あるいはアル
コール変性シリコンと二塩基酸とのオリゴマー化度を変
えた系で反応させ、第１表に示すエステル化生成物を得
た。After the reaction was completed, the acid value was measured.^V・92) 190 g of stearyl alcohol was added in an amount corresponding to this value. Here, the temperature of the system was returned to 160 to 250°C, and the reaction was continued for further 10 hours while stirring well. After the reaction is complete,
The catalyst was filtered off, then decolorized using activated clay, and deodorized by blowing in steam under reduced pressure to obtain the desired product (Sample No. 1). Thereafter, the reaction was carried out in the same manner in a system in which the composition of dibasic acid and alcohol was changed, or in a system in which the degree of oligomerization of alcohol-modified silicon and dibasic acid was changed, to produce the esterified products shown in Table 1. Obtained.
実施例３ エステル化生成物の安定性試験人体に対する
一次刺激性を閉塞バッチテストによって次のように検討
した。Example 3 Stability test of esterified product The primary irritation to the human body was investigated by a closed batch test as follows.
すなわち上腕層側部表皮の角質および表皮上の皮脂を除
き、１インチ四方のリント布に試料を塗布し、これを皮
膚表面に貼布し、油紙で覆い、紙絆創膏で四方を井桁に
とめ、この上をさらに線帯で押さえる。健康人２０名に
対しこのテストを実施し、２４時間後、４８時間後、１
週間後にそれぞれ判定を行ったが、本エステル化生成物
（試料隘１〜６）はいずれも全く刺激性が認められず、
化粧品油剤として有用である。That is, remove the dead skin and sebum on the epidermis of the side epidermis of the upper arm layer, apply the sample to a 1-inch square lint cloth, apply this to the skin surface, cover with oiled paper, and fasten the squares on all sides with paper adhesive plasters. Press the top with a wire belt. This test was conducted on 20 healthy people, and after 24 hours and 48 hours, 1
Judgments were made after a week, and none of the esterified products (sample sizes 1 to 6) were found to be irritating.
Useful as a cosmetic oil.
さらに塗布後の発臭試験を次の如〈実施した。Furthermore, an odor test after application was carried out as follows.
すなわち上腕部に２インチ四方に試料約０．２ｇを塗布
し、１０分後、２０分後、３０分後、１時間後、４時間
後、８時間後にそれぞれ臭覚により臭気を判定した。健
康人２０名に対してこの試験を行ったが本エステル化生
成物（試料隊１〜６）のいずれも臭気は全く感じられな
かった。That is, about 0.2 g of the sample was applied to a 2-inch square area on the upper arm, and the odor was determined by smell after 10 minutes, 20 minutes, 30 minutes, 1 hour, 4 hours, and 8 hours. This test was conducted on 20 healthy people, and no odor was detected in any of the esterified products (samples 1 to 6).
実施例４ 配合例
（ＩＩ０紅
キャンデリラロウ
カルナウバ′ロウ
セレシン
マイクロクリスタリンワックス
試料階１
流動パラフィン
トリー２−エチルへキサン酸
グリセリル
リンゴ酸ジイソステアリル
赤色２０２号
赤色２２６号
黄色４号アルミニウムレーキ
黒酸化鉄
香料、酸化防止剤
（２）ファンデーション（ケーキ型）
流動パラフィン
セスキオレイン酸ソルビタン
試料寛２
８．０％
５．０〃
５．０〃
５．０〃
７．０〃
１０．０ 〃
４０．０＃
２０．０〃
適量
適量
適量
適量
適量
８．０％
３．０＃
６．０〃
酸化チタン １０．０％コ
ロイタルカオリン ２７．０＝タルク
４２゜２〃ベンガラ
０・６″黄酸化鉄
２．９・黒酸化鉄
０・３″防腐剤、香料
適量（３）へ７リキソド
ポリオキシプロピレンブチルエーテル（４０ＰＯ）４．
０％
試料階４ １．０ 〃ア
クリル樹脂）′ルカノールアミン液 ２．Ｏ〃ポリア
ルキレングリコール誘導体 １３．０ 〃エタノー
ル ６２．０〃香料
０．８・色素
０．２〃精製水
１７．０〜（４）クリームリンス
１．３〜ブチレングリコール ３．０％塩
化ジステアリルジメチルアンモニウム３．０〃セタノー
ル ２，０％モノステアリ
ン酸グリセリル ２．０１ｔ流動パラフイン
０．８Ｎ試料ＮＱ、５
１．２〃防腐剤
適量香料
適量精製水にて 全量１００％
（５）エモリエントクリーム
試料ｔｉｈ ３ ３．０％
ステアリン酸 １５．０〃モノ
ステアリン酸グリセリル １．５′ｔポリオ
キシプロピレンブチルエーテル（４０ＰＯ）５．０〃
プロピレングリコール １０．Ｏｌ／防
腐剤 適量酸化防止剤
適量香料
適量精製水にて
全量１００％（６）エモリエントローション
セレシン １．０％試料
１ｌｋＬ６ １．５％ミツ
ロウ ２．Ｏ〃カルナウ
バロウ ２．０〃流動パラフイ
ン ３０．０ 〃ソルビタンセス
キオレイン酸エステル ４．０〃ポリオキシエチレンソ
ルビタンモノオレイン酸エステル（２０ＥＯ）
２．０〃ステアリン酸アルミニウム
０．３〃グリセリン
１０．０ 〃防腐剤
適量酸化防止剤 適量香料
通量精製水にて
全量１００％ｆｆ）発明の効果
本発明に係るエステル化生成物は淡色、無臭であり、ア
ルコール変成シリコンとのオリゴマーを形成する二塩基
酸の組成ならびにオリゴマー化度を変えることにより、
あるいはこのアルコール変成シリコンと二塩基酸のオリ
ゴマーに反応させる脂肪酸の組成ならびに仕込み比を調
節することにより、潤滑性、粘性、感触、あるいはワッ
クスを始めとする各種油剤、溶剤に対する相溶性など、
またその他の各種物性を自由に変えることが可能である
。また、粘性を上げてもべとつき感が少なく同一粘度の
シリコンオイルと比較した場合、脂ぎった光沢も少なく
、べとつきがなく、かつシリコンオイルに特有の滑り性
、撥水性、つやなどがそのまま保持されている。Example 4 Formulation example (II0 Red candelilla wax carnauba' wax ceresin microcrystalline wax Sample level 1 Liquid paraffin triglyceryl 2-ethylhexanoate Diisostearyl malate Red No. 202 Red No. 226 Yellow No. 4 Aluminum lake Black oxide Iron fragrance, antioxidant (2) Foundation (cake type) Liquid paraffin sorbitan sesquioleate sample 2 8.0% 5.0〃 5.0〃 5.0〃 7.0〃 10.0 〃 40.0 # 20.0〃 Proper amount Proper amount Proper amount Proper amount 8.0% 3.0 # 6.0〃 Titanium oxide 10.0% Colloidal kaolin 27.0 = Talc 42゜2〃 Red iron
0.6″ yellow iron oxide
2.9・Black iron oxide
0.3″ preservatives, fragrances
4. Add appropriate amount (3) of 7 lyxodo polyoxypropylene butyl ether (40PO).
0% Sample floor 4 1.0 〃Acrylic resin)' Lucanolamine liquid 2. O Polyalkylene glycol derivative 13.0 Ethanol 62.0 Fragrance
0.8・Pigment
0.2〃Purified water
17.0~(4) Cream rinse 1.3~Butylene glycol 3.0% Distearyldimethylammonium chloride 3.0〃Cetanol 2.0% Glyceryl monostearate 2.01t Liquid paraffin
0.8N sample NQ, 5
1.2 Preservatives
Appropriate amount of fragrance
100% with appropriate amount of purified water
(5) Emollient cream sample tih 3 3.0%
Stearic acid 15.0 Glyceryl monostearate 1.5't polyoxypropylene butyl ether (40PO) 5.0 Propylene glycol 10. Ol/Preservative Appropriate amount of antioxidant
Appropriate amount of fragrance
With appropriate amount of purified water
Total amount 100% (6) Emollient lotion Ceresin 1.0% sample 1 lkL6 1.5% Beeswax 2. O Carnauba wax 2.0 Liquid paraffin 30.0 Sorbitan sesquioleate 4.0 Polyoxyethylene sorbitan monooleate (20EO)
2.0 Aluminum stearate
0.3〃Glycerin
10.0 Preservatives
Appropriate amount of antioxidant, appropriate amount of fragrance
With purified water
Total amount 100% ff) Effects of the invention The esterified product according to the present invention is light-colored and odorless, and by changing the composition of the dibasic acid that forms an oligomer with alcohol-modified silicon and the degree of oligomerization,
Alternatively, by adjusting the composition and charging ratio of the fatty acid reacted with this alcohol-modified silicone and dibasic acid oligomer, we can improve the lubricity, viscosity, feel, and compatibility with various oils and solvents including wax.
Further, various other physical properties can be freely changed. In addition, even when the viscosity is increased, it does not feel sticky, and when compared to silicone oil of the same viscosity, there is less greasy shine and no stickiness, and it retains the slipperiness, water repellency, gloss, etc. that are characteristic of silicone oil. There is.
そして皮膚に刺激を与えず、また皮膚に対してずくれた
親和性、感触を有し、乳化性、保湿性、エモリエント性
を備えた安定性の高い物質でありこれを油剤として用い
れば、品質の優れた各種化粧料が得られる。It is a highly stable substance that does not irritate the skin, has a unique affinity and texture to the skin, and has emulsifying, moisturizing, and emollient properties. Various excellent cosmetics can be obtained.
Claims (2)
ール変性シリコンを二塩基酸でオリゴマー化したジカル
ボン酸と、アルコールとのエステル化生成物。 ▲数式、化学式、表等があります▼・・・・・（ I ） ▲数式、化学式、表等があります▼・・・・・（II） Ｒ＿１、Ｒ＿２はアルコールの残基であり、Ｒ＿１＝Ｒ
＿２またはＲ＿１≠Ｒ＿２Ｒ＿３は−（ＣＨ＿２）＿ｍ
−または▲数式、化学式、表等があります▼または▲数
式、化学式、表等があります▼（Ｋは１〜１０の整数、
ｎは０または１以上の整数、ｍは１〜１８の整数）(1) An esterification product of alcohol and a dicarboxylic acid obtained by oligomerizing alcohol-modified silicon with a dibasic acid, represented by general formula (I) or (II). ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(II) R_1 and R_2 are residues of alcohol, and R_1=R
_2 or R_1≠R_2R_3 is -(CH_2)_m
- or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (K is an integer from 1 to 10,
n is an integer of 0 or 1 or more, m is an integer of 1 to 18)
種以上を配合してなる化粧料。(2) one or two of the esterification products according to claim 1;
Cosmetics made by blending more than one species.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2274243A JP3046341B2 (en) | 1990-10-12 | 1990-10-12 | Esterification products and cosmetics containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2274243A JP3046341B2 (en) | 1990-10-12 | 1990-10-12 | Esterification products and cosmetics containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04149233A true JPH04149233A (en) | 1992-05-22 |
| JP3046341B2 JP3046341B2 (en) | 2000-05-29 |
Family
ID=17538997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2274243A Expired - Fee Related JP3046341B2 (en) | 1990-10-12 | 1990-10-12 | Esterification products and cosmetics containing them |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3046341B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5891914A (en) * | 1991-03-27 | 1999-04-06 | Special Advanced Biomaterials, Inc. | Bioactive topical siloxane compositions having enhanced performance and safety |
| JP2004256515A (en) * | 2003-02-04 | 2004-09-16 | Nippon Fine Chem Co Ltd | Oily base, cosmetic and skin care preparation for external use containing the same |
-
1990
- 1990-10-12 JP JP2274243A patent/JP3046341B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5891914A (en) * | 1991-03-27 | 1999-04-06 | Special Advanced Biomaterials, Inc. | Bioactive topical siloxane compositions having enhanced performance and safety |
| JP2004256515A (en) * | 2003-02-04 | 2004-09-16 | Nippon Fine Chem Co Ltd | Oily base, cosmetic and skin care preparation for external use containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3046341B2 (en) | 2000-05-29 |
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