JP6527347B2 - Transparent to translucent cosmetics - Google Patents
Transparent to translucent cosmetics Download PDFInfo
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- JP6527347B2 JP6527347B2 JP2015035264A JP2015035264A JP6527347B2 JP 6527347 B2 JP6527347 B2 JP 6527347B2 JP 2015035264 A JP2015035264 A JP 2015035264A JP 2015035264 A JP2015035264 A JP 2015035264A JP 6527347 B2 JP6527347 B2 JP 6527347B2
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- polyoxyethylene
- resveratrol
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- 239000002537 cosmetic Substances 0.000 title claims description 24
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical class C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 claims description 39
- -1 polyoxyethylene Polymers 0.000 claims description 33
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 22
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 16
- 239000002736 nonionic surfactant Substances 0.000 claims description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- 150000005846 sugar alcohols Polymers 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 229940058015 1,3-butylene glycol Drugs 0.000 claims description 8
- 235000019437 butane-1,3-diol Nutrition 0.000 claims description 8
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 6
- 239000004359 castor oil Substances 0.000 claims description 5
- 235000019438 castor oil Nutrition 0.000 claims description 5
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 5
- 150000005215 alkyl ethers Chemical class 0.000 claims description 4
- QYIXCDOBOSTCEI-QCYZZNICSA-N (5alpha)-cholestan-3beta-ol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-QCYZZNICSA-N 0.000 claims description 2
- QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 claims description 2
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 18
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 235000021283 resveratrol Nutrition 0.000 description 7
- 229940016667 resveratrol Drugs 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000012790 confirmation Methods 0.000 description 4
- 150000004676 glycans Chemical class 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 229920001282 polysaccharide Polymers 0.000 description 4
- 239000005017 polysaccharide Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 3
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 3
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 3
- 229960002216 methylparaben Drugs 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 1
- BDOYKFSQFYNPKF-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid;sodium Chemical compound [Na].[Na].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O BDOYKFSQFYNPKF-UHFFFAOYSA-N 0.000 description 1
- UNWFFCPRJXMCNV-UHFFFAOYSA-N 3-[dodecanoyl(methyl)amino]propanoic acid Chemical compound CCCCCCCCCCCC(=O)N(C)CCC(O)=O UNWFFCPRJXMCNV-UHFFFAOYSA-N 0.000 description 1
- XPFCZYUVICHKDS-UHFFFAOYSA-N 3-methylbutane-1,3-diol Chemical compound CC(C)(O)CCO XPFCZYUVICHKDS-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- BIVBRWYINDPWKA-VLQRKCJKSA-L Glycyrrhizinate dipotassium Chemical compound [K+].[K+].O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@H]1CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@](C)(CC[C@@]5(CC[C@@]4(C)[C@]3(C)CC[C@H]2C1(C)C)C)C(O)=O)C([O-])=O)[C@@H]1O[C@H](C([O-])=O)[C@@H](O)[C@H](O)[C@H]1O BIVBRWYINDPWKA-VLQRKCJKSA-L 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- BACYUWVYYTXETD-UHFFFAOYSA-N N-Lauroylsarcosine Chemical compound CCCCCCCCCCCC(=O)N(C)CC(O)=O BACYUWVYYTXETD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 108050002485 Sirtuin Proteins 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000008406 cosmetic ingredient Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 229940101029 dipotassium glycyrrhizinate Drugs 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Chemical class 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000003716 rejuvenation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XFLNVMPCPRLYBE-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;tetrahydrate Chemical compound O.O.O.O.[Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O XFLNVMPCPRLYBE-UHFFFAOYSA-J 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Description
本発明は、難溶性物の水添レスベラトロールを安定に可溶化した、透明ないし半透明の化粧料に関する。
The present invention relates to a transparent to translucent cosmetic which stably solubilizes a poorly soluble hydrogenated resveratrol.
レスベラトロールは、サンタベリーやブドウなどに含まれるポリフェノールの一種で若返りの成分とも呼ばれ、化粧品やサプリメントに配合され美容成分として高い注目を集めている。強い抗酸化力を持ち、細胞の酸化を防ぐとともに、老化要因を抑制し、寿命を延ばすとされる長寿遺伝子（サーチュイン遺伝子）を活性化することで、若々しさを保つ効果が期待されている、注目のエイジングケア成分である（特許文献１）。 Resveratrol is a kind of polyphenol contained in Santa Berry and grapes and is also referred to as a rejuvenating ingredient, and it is incorporated into cosmetics and supplements and is drawing high attention as a cosmetic ingredient. It is expected to have the effect of maintaining youthfulness by activating a longevity gene (sirtuin gene) that has strong antioxidant power, prevents oxidation of cells, suppresses aging factors, and prolongs lifespan. Aging care ingredients of interest. (Patent Document 1).
しかし、レスベラトロールは分子構造中に不飽和結合があり、化粧料や皮膚外用剤の製剤中に配合した場合、大変酸化されやすく、分解、着色し、効果が著しく低下するという問題があった。そこで我々は、レスベラトロールを水素添加することで、レスベラトロールの効果を維持しながら、安定に化粧品製剤中に配合することが可能なレスベラトロール誘導体を得た。 However, resveratrol has an unsaturated bond in its molecular structure, and when it is incorporated in a preparation of a cosmetic or a skin external preparation, it has a problem that it is very easily oxidized, degraded and colored, and its effect is significantly reduced. . Therefore, we obtained resveratrol derivatives that can be stably incorporated into cosmetic preparations while maintaining the effect of resveratrol by hydrogenating resveratrol.
ところが、得られた水添レスベラトロールは、一般に化粧料に使用される油などの油性原料や水などの成分に非常に溶解し難いという性質を持ち、化粧料への配合が困難であった。従来、このような難溶性物質の化粧料への配合方法としては、当該難溶性物質を高温で油相成分中に溶解して、それを乳化する方法があり、さらに溶解性を高める目的で、常温で液状の脂肪酸、高級アルコール等が併用されてきた。 However, the obtained hydrogenated resveratrol has the property of being very difficult to dissolve in components such as oil and water generally used in cosmetics, and it has been difficult to blend in cosmetics. . Conventionally, as a method of blending such poorly soluble substances into cosmetics, there is a method of dissolving the poorly soluble substances in an oil phase component at high temperature and emulsifying the same, and for the purpose of further enhancing the solubility, Liquid fatty acids, higher alcohols, etc. have been used in combination at normal temperature.
しかしながらこれらの方法をもってしても、水添レスベラトロールを製剤中に安定に溶解させるには不充分であり、経時的に水添レスベラトロールが結晶化し、製剤中に析出することを防止することは出来なかった。また、これらの方法を利用するとしても適用出来るのは乳化系のみであり、水添レスベラトロールを製剤中に可溶化させた透明ないし半透明の化粧料を得る方法は見出されていない。 However, even with these methods, it is insufficient to stably dissolve hydrogenated resveratrol in the preparation, and it prevents crystallization of hydrogenated resveratrol over time and precipitation in the preparation. I could not do that. Also, even if these methods are used, only an emulsifying system can be applied, and no method has been found to obtain a transparent to translucent cosmetic in which hydrogenated resveratrol is solubilized in a preparation.
本発明は難溶性の水添レスベラトロールを安定に可溶化し、結晶析出の無い、透明ないし半透明の外観である化粧料を提供することを課題とした。 An object of the present invention is to stably dissolve poorly soluble hydrogenated resveratrol and to provide a cosmetic having a transparent to translucent appearance without crystal precipitation.
このような水添レスベラトロールの溶解性や、経時的な安定性を改良するために本発明者は鋭意研究した結果、特定の非イオン性界面活性剤と特定の多価アルコールの組み合わせが水添レスベラトロールの溶解性や、経時的な安定性を大きく改善し、安定に可溶化できることを見出した。より具体的には、ＨＬＢが９〜２０の範囲にある非イオン性界面活性剤、及び液状の多価アルコールを用いることにより水添レスベラトロールを安定性良く可溶化できることを見出し、結晶析出の無い、透明ないし半透明の外観を有する化粧料である本発明を完成した。 As a result of intensive research conducted by the inventor in order to improve the solubility and stability over time of such hydrogenated resveratrol, a combination of a specific nonionic surfactant and a specific polyhydric alcohol is water. It has been found that the solubility and stability with time of the resveratrol added can be greatly improved and can be stably solubilized. More specifically, it has been found that hydrogenated resveratrol can be solubilized with good stability by using a nonionic surfactant having a HLB in the range of 9 to 20 and a liquid polyhydric alcohol, and it is possible to precipitate crystals. The present invention has been completed, which is a cosmetic having no transparent or translucent appearance.
本発明は、美容効果が高いが、難溶性の水添レスベラトロールを、特定成分の組合せにより、可溶化し、透明ないし半透明のローション製剤に配合することができる。本発明により調製した透明ないし半透明の化粧料は、経時での水添レスベラトロールの結晶は生じなかった。 According to the present invention, hydrogenated esveratrol, which has high cosmetic effect, but is poorly soluble, can be solubilized and formulated into a transparent to translucent lotion preparation by a combination of specific components. The transparent to translucent cosmetic prepared according to the present invention did not produce crystals of hydrogenated resveratrol over time.
本発明に使用する水添レスベラトロールは、レスベラトロールを酢酸エチル、テトラヒドロフラン、イソプロパノール、メタノールなどの溶媒中、パラジウムなどの触媒を使用し、水素添加することで得られる。 The hydrogenated resveratrol used in the present invention can be obtained by hydrogenating resveratrol using a catalyst such as palladium in a solvent such as ethyl acetate, tetrahydrofuran, isopropanol, or methanol.
本発明で用いる非イオン性界面活性剤としては、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンポリオキシプロピレンアルキルエーテル、ポリオキシエチレンポリオキシプロピレン共重合体、ポリオキシエチレンステロール、ポリオキシエチレン水素添加ステロール、ポリオキシエチレンアルキルアミノエーテル、ポリオキシエチレンアルキルアミド、脂肪酸アルカノールアミド、ポリオキシエチレン脂肪酸アルカノールアミド、ポリオキシエチレン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ポリオキシエチレンソルビット脂肪酸エステル、ポリオキシエチレンヒマシ油、ポリオキシエチレン硬化ヒマシ油、ポリグリセリン脂肪酸エステル、ポリオキシエチレングリセリン脂肪酸エステル、ショ糖脂肪酸エステル、アルキルポリグルコシド、メチルグルコシド脂肪酸エステル、ポリエーテル変性シリコーン等が挙げられる。これらの界面活性剤は、ＨＬＢが９〜２０の範囲にあることが好ましい。これらの中で、ＨＬＢが９〜２０の範囲にあるポリオキシエチレン硬化ヒマシ油、ポリオキシエチレンポリオキシプロピレンアルキルエーテル、ポリオキシエチレンポリオキシプロピレン共重合体、ポリオキシエチレンフィトステロール、ポリオキシエチレンフィトスタノール、ポリオキシエチレンコレスタノールが特に好ましい。 As the nonionic surfactant used in the present invention, polyoxyethylene alkyl ether, polyoxyethylene polyoxypropylene alkyl ether, polyoxyethylene polyoxypropylene copolymer, polyoxyethylene sterol, polyoxyethylene hydrogenated sterol, Polyoxyethylene alkylaminoether, polyoxyethylene alkylamide, fatty acid alkanolamide, polyoxyethylene fatty acid alkanolamide, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbit fatty acid ester, polyoxyethylene castor oil, Polyoxyethylene hydrogenated castor oil, polyglycerin fatty acid ester, polyoxyethylene glycerin fatty acid ester, sucrose fatty acid Ester, alkyl polyglucoside, methyl glucoside fatty acid esters, polyether-modified silicone, and the like. These surfactants preferably have an HLB in the range of 9-20. Among them, polyoxyethylene hydrogenated castor oil having a HLB in the range of 9 to 20, polyoxyethylene polyoxypropylene alkyl ether, polyoxyethylene polyoxypropylene copolymer, polyoxyethylene phytosterol, polyoxyethylene phytostanol And polyoxyethylene cholestanol are particularly preferred.
本発明で用いる液状の多価アルコールとしては、エチレングリコール、プロピレングリコール、１，３−ブチレングリコール、ジプロピレングリコール、イソプレングリコール、ポリエチレングリコール、グリセリン、ポリグリセリン等を用いることができる。これらの中でプロピレングリコール、１，３−ブチレングリコール、ジプロピレングリコールが好ましい。 As liquid polyhydric alcohols used in the present invention, ethylene glycol, propylene glycol, 1,3-butylene glycol, dipropylene glycol, isoprene glycol, polyethylene glycol, glycerin, polyglycerin and the like can be used. Among these, propylene glycol, 1,3-butylene glycol and dipropylene glycol are preferred.
本発明の透明ないし半透明の化粧料における、水添レスベラトロールとＨＬＢが９〜２０の範囲にある非イオン性界面活性剤の質量組成比は、水添レスベラトロール／非イオン性界面活性剤＝０．１／９９．９〜５０／５０であれば良く、好ましくは、水添レスベラトロール／非イオン性界面活性剤＝０．１／９９．９〜４０／６０である。また本発明の透明ないし半透明の化粧料中の水添レスベラトロールと非イオン性界面活性剤の混合物に対する、液状の多価アルコールの質量組成比は、（水添レスベラトロール＋非イオン性界面活性剤混合物）／（液状の多価アルコール）＝１０／９０〜９９．９／０．１であれば良く、好ましくは、（水添レスベラトロール+非イオン性界面活性剤混合物）／（液状の多価アルコール）＝２０／８０〜８０／２０である。 The mass composition ratio of hydrogenated resveratrol and nonionic surfactant having HLB in the range of 9 to 20 in the transparent to translucent cosmetic of the present invention is hydrogenated resveratrol / nonionic surfactant The agent may be 0.1 / 99.9 to 50/50, and preferably, hydrogenated resveratrol / nonionic surfactant = 0.1 / 99.9 to 40/60. Further, the mass composition ratio of liquid polyhydric alcohol to the mixture of hydrogenated resveratrol and nonionic surfactant in the transparent to translucent cosmetic of the present invention is (hydrogenated resveratrol + nonionic Surfactant mixture) / (liquid polyhydric alcohol) = 10/90 to 99.9 / 0.1 is preferable, and preferably (hydrogenated resveratrol + nonionic surfactant mixture) / ( Liquid polyhydric alcohol) = 20/80 to 80/20.
本発明の水添レスベラトロールを可溶化した透明ないし半透明の化粧料の調製方法は、水添レスベラトロール、ＨＬＢが９〜２０の範囲にある非イオン性界面活性剤、及び液状の多価アルコールを８０℃まで加温溶解し、これに８０℃に加温した他の成分及び水を加えて混合した後、室温まで冷却する。
化粧料中の水添レスベラトロールとしての添加量は０．０００１〜５質量％、好ましくは０．００１〜２．０質量％配合されるように本組成物を添加すれば良い。
The method for preparing a transparent or translucent cosmetic preparation in which the hydrogenated resveratrol according to the present invention is solubilized includes hydrogenated resveratrol, a nonionic surfactant having an HLB in the range of 9 to 20, and a liquid poly The polyhydric alcohol is dissolved by heating to 80 ° C., the other components heated to 80 ° C. and water are added and mixed, and then cooled to room temperature.
The composition may be added such that the amount of hydrogenated resveratrol added to the cosmetic is 0.0001 to 5% by mass, preferably 0.001 to 2.0% by mass.
本発明の透明ないし半透明の化粧料には、上記成分のほかに、本発明の効果を損なわない範囲で一般的に化粧料に配合される成分として、本発明の可溶化成分以外の界面活性剤、本発明の可溶化成分以外の多価アルコール、糖、高分子化合物、生理活性成分、経皮吸収促進剤、溶媒、酸化防止剤、香料、防腐剤等を配合することができる。
以下に実施例を挙げて本発明を具体的に説明するが、本発明の技術範囲がこれらに限定されるものではない。なお配合量は質量％で示す。
In the transparent to translucent cosmetic of the present invention, in addition to the above-mentioned components, surface active agents other than the solubilizing component of the present invention can be used as components generally blended in the cosmetic as long as the effects of the present invention are not impaired. Agents, polyhydric alcohols other than the solubilizing component of the present invention, sugars, polymer compounds, physiologically active ingredients, transdermal absorption enhancers, solvents, antioxidants, perfumes, preservatives, etc. can be blended.
EXAMPLES Although an Example is given to the following and this invention is concretely demonstrated, the technical scope of this invention is not limited to these. In addition, the compounding quantity is shown by mass%.
（製造例）水添レスベラトロールの製造
３００ｍｌガラス製オートクレーブに、レスベラトロール２０ｇ、メタノール１３０ｇ、５％Ｐｄ／Ｃ０．２ｇを仕込み、窒素置換を３回、水素置換を３回行った。撹拌下、室温で、水素圧３Ｋｇ／ｃｍ２で３時間反応させた。反応後、反応液をろ過し、Ｐｄ／Ｃを除き、減圧下、メタノールを留去し、１９．７４ｇ（収率９７．８２％）の水添レスベラトロールを得た。
分析値：水酸基価６７８．７、融点１６０．５℃、ＧＣ面積％ ９９．９４％
得られた化合物の１H-NMRを測定し、解析したところ、目的の水添レスベラトロールであることを確認した。
１H-NMR（400MHｚ,DMSO-D6） 9.076ppm（s,1H）、8.989ppm（s,2H）、6.9576-6.9365ppm（d,2H）、6.6237-6.5888ppm（d,2H）、6.0161ppm（s,1H）、6.0109ppm（s,1H）、5.9800-5.9697ppm（m,1H）、2.6552-2.5360ppm（m,4H）
Production Example Production of Hydrogenated Resveratrol 20 g of resveratrol, 130 g of methanol and 0.2 g of 5% Pd / C were charged into a 300 ml glass autoclave, and nitrogen substitution was performed three times and hydrogen substitution was performed three times. Under stirring, the reaction was performed at room temperature under a hydrogen pressure of 3 Kg / cm 2 for 3 hours. After the reaction, the reaction solution was filtered to remove Pd / C, and methanol was distilled off under reduced pressure to obtain 19.74 g (yield 97.82%) of hydrogenated resveratrol.
Analysis value: Hydroxyl value 678.7, melting point 160.5 ° C., GC area% 99.94%
The 1 H-NMR of the obtained compound was measured and analyzed to confirm that it was the desired hydrogenated resveratrol.
1 H-NMR (400 MHz, DMSO-D6) 9.076 ppm (s, 1 H), 8. 899 ppm (s, 2 H), 6.9576-6.9365 ppm (d, 2 H), 6.6237-6.5 888 ppm (d, 2 H), 6.0161 ppm (d s, 1H), 6.0109 ppm (s, 1 H), 5.98800-5.9697 ppm (m, 1 H), 2.6552-2.5360 ppm (m, 4 H)
（１）試料の調製
水添レスベラトロール、非イオン性界面活性剤、及び液状の多価アルコールを８０℃に加温混合し、水添レスベラトロールを溶解させる。更にこれに８０℃に加温した他の成分及び水を加えて撹拌した後、室温まで冷却し、終了とした。
(1) Preparation of sample Hydrogenated resveratrol, nonionic surfactant and liquid polyhydric alcohol are heated and mixed at 80 ° C. to dissolve hydrogenated resveratrol. Furthermore, the other component and water which were heated at 80 degreeC were added and stirred, it cooled to room temperature and was complete | finished.
（２）評価方法（結晶析出の確認）
結晶析出の確認は、本発明品及び比較品の試料をガラス製の密閉容器にとり、直後の状態を目視で下記基準により評価した。さらにこれらを蓋で密閉して５±０．５℃、４５±０．５℃の恒温槽に１ヶ月間放置した後、同様に目視で下記基準により評価した。
◎：全く結晶が確認されない
○：僅かに結晶が確認された
×：結晶（澱または浮遊物）が確認された
(2) Evaluation method (confirmation of crystal precipitation)
The confirmation of the crystal deposition was carried out by taking samples of the product of the present invention and the comparative product in a closed container made of glass, and immediately evaluating the state immediately after based on the following criteria. Furthermore, after sealing these with a lid and leaving them in a thermostat at 5 ± 0.5 ° C. and 45 ± 0.5 ° C. for 1 month, they were similarly visually evaluated according to the following criteria.
:: No crystals were observed at all. :: Crystals were slightly confirmed. X: Crystals (freeze or float) were confirmed.
（３）評価方法（透明度の確認）
透明度の確認は、本発明品及び比較品の試料を、断面が１０×１０ｍｍの石英セルを用いて、分光光度計により波長６８０ｎｍにおける透過率を測定した（対照液は精製水とした）。透過率が６０％未満を白濁、６０〜８０％を半透明、８０％を超えた場合を透明とした。測定は調製直後と調製後に５℃で３か月間保管したものについて実施した。試料がクリーミングあるいは分離している場合は、測定不可とした。
(3) Evaluation method (confirmation of transparency)
For confirmation of transparency, the transmittance of a sample of the present invention and a comparative product was measured at a wavelength of 680 nm using a quartz cell having a cross section of 10 × 10 mm (a control solution was purified water). When the transmittance was less than 60%, it became white turbidity, 60-80% was semitransparent, and when it exceeded 80%, it was transparent. The measurement was carried out on those stored immediately after preparation and after preparation for 3 months at 5 ° C. If the sample was creaming or separated, it was not possible to measure.
（４）結果
結果を表１及び表２に示す。本発明の水添レスベラトロールを可溶化した、透明ないし半透明の化粧料は、５℃で１ヶ月後、及び４５℃で１ヶ月後においても極めて良好な可溶化状態であった。
ローション （質量％）
Ａ 水添レスベラトロール ０．１０
ポリオキシエチレン６０硬化ヒマシ油 １．５０
ジプロピレングリコール ８．００
Ｂ ヒドロキシエチルセルロース ０．０２
水溶性多糖類水溶液 １．００
１，３−ブチレングリコール ２．５０
メチルパラベン ０．１０
水 残部
（調製法）Ａ相を８０℃で均一に溶解し、そこに予め８０℃に加温したＢ相を添加・混合した後、室温まで冷却し、調製終了とする。
（外観）外観は、蛍光透明であった。蛍光は、水溶性多糖類由来である。
Lotion (mass%)
A hydrogenated resveratrol 0.10
Polyoxyethylene 60 Hardened Castor Oil 1.50
Dipropylene glycol 8.00
B hydroxyethyl cellulose 0.02
Water-soluble polysaccharide aqueous solution 1.00
1,3-butylene glycol 2.50
Methyl paraben 0.10
Water Residue (Preparation Method) A phase is uniformly dissolved at 80 ° C. B phase preheated to 80 ° C. is added thereto and mixed, and then cooled to room temperature to complete the preparation.
(Appearance) The appearance was fluorescent and transparent. The fluorescence is from a water soluble polysaccharide.
美白ローション （質量％）
Ａ 水添レスベラトロール ０．１０
ポリオキシエチレン３０ポリオキシプロピレン
６デシルテトラデシルエーテル １．５０
１，３−ブチレングリコール ８．００
Ｂ リン酸Ｌ−アスコルビルマグネシウム ３．００
グリセリン １０．００
１，３−ブチレングリコール ２．５０
メチルパラベン ０．１５
プロピルパラベン ０．１０
エチレンジアミン４酢酸４ナトリウム ０．１０
クエン酸ナトリウム ０．５０
水 残部
（調製法）実施例３と同様の方法で調製した。
（外観）外観は、透明であった。
Whitening lotion (mass%)
A hydrogenated resveratrol 0.10
Polyoxyethylene 30 Polyoxypropylene
6 decyl tetradecyl ether 1.50
1,3-butylene glycol 8.00
B phosphate L-ascorbyl magnesium 3.00
Glycerin 10.00
1,3-butylene glycol 2.50
Methyl paraben 0.15
Propyl paraben 0.10
Ethylenediaminetetraacetic acid tetrasodium 0.10
Sodium citrate 0.50
Water Residue (Preparation Method) It was prepared in the same manner as in Example 3.
(Appearance) The appearance was transparent.
洗顔ローション （質量％）
Ａ 水添レスベラトロール ０．０１
ポリオキシエチレン３０コレスタノールエーテル １．５０
プロピレングリコール ８．００
Ｂ ラウロイルサルコシンナトリウム（３０％水溶液） ９．００
ラウロイルメチルアラニンナトリウム（３０％水溶液）１２．００
ヒドロキシエチルセルロース ０．０２
水溶性多糖類水溶液 １．００
グリセリン １０．００
１，３−ブチレングリコール ２．５０
メチルパラベン ０．１０
水 残部
（調製法）実施例３と同様の方法で調製した。
（外観）外観は、蛍光透明であった。
Facial wash lotion (mass%)
A hydrogenated resveratrol 0.01
Polyoxyethylene 30 Corestanol Ether 1.50
Propylene glycol 8.00
B lauroyl sarcosine sodium (30% aqueous solution) 9.00
Sodium lauroyl methyl alanine (30% aqueous solution) 12.00
Hydroxyethylcellulose 0.02
Water-soluble polysaccharide aqueous solution 1.00
Glycerin 10.00
1,3-butylene glycol 2.50
Methyl paraben 0.10
Water Residue (Preparation Method) It was prepared in the same manner as in Example 3.
(Appearance) The appearance was fluorescent and transparent.
美容エッセンス （質量％）
Ａ 水添レスベラトロール １．００
ポリオキシエチレン２０ポリオキシプロピレン
４セチルエーテル １．５０
ジプロピレングリコール １０．００
１，３−ブチレングリコール ８．００
Ｂ エチレンジアミン４酢酸２ナトリウム ０．０５
安息香酸ナトリウム ０．１０
グリチルリチン酸ジカリウム ０．１０
ヒドロキシエチルセルロース ０．０２
水溶性多糖類水溶液 ３．００
水 残部
（調製法）実施例３と同様の方法で調製した。
（外観）外観は、蛍光透明であった。
（結果）実施例３〜６の化粧品処方は調製直後、５℃１ヶ月後、４５℃１ヶ月後の条件で、水添レスベラトロールの結晶は確認されなかった。
Beauty essence (mass%)
A hydrogenated resveratrol 1.00
Polyoxyethylene 20 Polyoxypropylene
4 cetyl ether 1.50
Dipropylene glycol 10.00
1,3-butylene glycol 8.00
B Ethylenediaminetetraacetic acid disodium 0.05
Sodium benzoate 0.10
Dipotassium glycyrrhizinate 0.10
Hydroxyethylcellulose 0.02
Water-soluble polysaccharide aqueous solution 3.00
Water Residue (Preparation Method) It was prepared in the same manner as in Example 3.
(Appearance) The appearance was fluorescent and transparent.
(Results) In the cosmetic formulations of Examples 3 to 6, no crystals of hydrogenated resveratrol were found immediately after preparation, after one month at 5 ° C. and one month after 45 ° C.
Claims (3)
Component (A) hydrogenated resveratrol represented by the following general formula (1): component (B) nonionic surfactant having HLB in the range of 9 to 20; component (C) polyhydric alcohol in liquid form; A transparent to translucent cosmetic characterized in that it is solubilized in water .
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