JP2016056149A - Skin cosmetic - Google Patents
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- JP2016056149A JP2016056149A JP2014185748A JP2014185748A JP2016056149A JP 2016056149 A JP2016056149 A JP 2016056149A JP 2014185748 A JP2014185748 A JP 2014185748A JP 2014185748 A JP2014185748 A JP 2014185748A JP 2016056149 A JP2016056149 A JP 2016056149A
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- 239000002537 cosmetic Substances 0.000 title claims abstract description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229930182496 polymethoxyflavone Natural products 0.000 claims abstract description 18
- -1 oxypropylene group Chemical group 0.000 claims abstract description 12
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- HOVAGTYPODGVJG-UVSYOFPXSA-N (3s,5r)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol Chemical compound COC1OC(CO)[C@@H](O)C(O)[C@H]1O HOVAGTYPODGVJG-UVSYOFPXSA-N 0.000 claims abstract description 9
- HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- 125000006353 oxyethylene group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 230000000694 effects Effects 0.000 abstract description 74
- 239000011148 porous material Substances 0.000 abstract description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000006866 deterioration Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 230000002123 temporal effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- ULSUXBXHSYSGDT-UHFFFAOYSA-N tangeretin Chemical compound C1=CC(OC)=CC=C1C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 ULSUXBXHSYSGDT-UHFFFAOYSA-N 0.000 description 10
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241001672694 Citrus reticulata Species 0.000 description 5
- OBIOZWXPDBWYHB-UHFFFAOYSA-N Nobiletin Natural products C1=CC(OC)=CC=C1C1=C(OC)C(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 OBIOZWXPDBWYHB-UHFFFAOYSA-N 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000006210 lotion Substances 0.000 description 5
- MRIAQLRQZPPODS-UHFFFAOYSA-N nobiletin Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 MRIAQLRQZPPODS-UHFFFAOYSA-N 0.000 description 5
- 229940058015 1,3-butylene glycol Drugs 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- IECRXMSGDFIOEY-UHFFFAOYSA-N Tangeretin Natural products COC=1C(OC)=C(OC)C(OC)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C=C1 IECRXMSGDFIOEY-UHFFFAOYSA-N 0.000 description 4
- 235000019437 butane-1,3-diol Nutrition 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 230000036548 skin texture Effects 0.000 description 4
- DGPHAUBUAGDZCS-UHFFFAOYSA-N 2-(2,3-dimethoxyphenyl)-3,5,6,7,8-pentamethoxychromen-4-one Chemical compound COC1=CC=CC(C2=C(C(=O)C3=C(OC)C(OC)=C(OC)C(OC)=C3O2)OC)=C1OC DGPHAUBUAGDZCS-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000555678 Citrus unshiu Species 0.000 description 2
- 240000000560 Citrus x paradisi Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- UMQJIGKYMZLXAH-UHFFFAOYSA-N 2-(2,3-dimethoxyphenyl)-3,5,6,7,8-pentamethoxychromen-4-one 2-(3,4-dimethoxyphenyl)-3,5,6,7,8-pentamethoxychromen-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(OC)C(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1.COC1=CC=CC(C2=C(C(=O)C3=C(OC)C(OC)=C(OC)C(OC)=C3O2)OC)=C1OC UMQJIGKYMZLXAH-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- ZDLYNMZEAFURQY-UHFFFAOYSA-N 5,6,7,8,3',4'-Hexamethoxyflavone Natural products COC=1C(OC)=C(OC)C(OC)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 ZDLYNMZEAFURQY-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 206010014970 Ephelides Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 208000003351 Melanosis Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008300 cosmetic paste Substances 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940113120 dipropylene glycol Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229960005082 etohexadiol Drugs 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Cosmetics (AREA)
Abstract
Description
本発明は、肌のキメを整える効果、毛穴を引き締める効果に優れ、化粧ノリの改善効果、化粧くずれの抑制効果を示すとともに、経時安定性に優れた皮膚化粧料に関する。 The present invention relates to a skin cosmetic that is excellent in the effect of trimming the texture of the skin, the effect of tightening pores, the effect of improving makeup, the effect of suppressing makeup loss, and the stability over time.
シミやソバカスを防止するために、美白作用を有する様々な化粧料が提案されている。例えば、特許文献１には、ポリメトキシフラボンを含有する化粧料組成物が美白効果に優れるとともに、うるおいを長時間保ち、肌にはりを与える効果、およびしわ抑制効果に優れ、経時安定性にも優れることが記載されている。
しかしながら、ポリメトキシフラボンを配合した化粧料は、肌に塗布したとき、肌のキメを整える効果、毛穴を引き締める効果、化粧ノリの改善効果、化粧くずれの抑制効果が十分ではないため、更なる改善が求められている。
Various cosmetics having a whitening effect have been proposed to prevent spots and freckles. For example, Patent Document 1 discloses that a cosmetic composition containing polymethoxyflavone is excellent in a whitening effect, has a moisturizing effect for a long period of time, has an effect of giving a skin tone, and has a wrinkle-suppressing effect, and also has stability over time. It is described that it is excellent.
However, cosmetics formulated with polymethoxyflavone, when applied to the skin, are not sufficiently effective in improving the texture of the skin, tightening pores, improving makeup, and preventing makeup slippage. Is required.
本発明の目的は、上記事情に鑑み、肌のキメを整える効果、毛穴を引き締める効果に優れ、化粧ノリの改善効果、化粧くずれの抑制効果を示すとともに、経時安定性に優れた皮膚化粧料の提供を目的とする。 In view of the circumstances described above, the object of the present invention is to provide a skin cosmetic that is excellent in skin texture, tightens pores, has an effect of improving makeup, and suppresses makeup loss, and has excellent stability over time. For the purpose of provision.
本発明者らは、上記課題を解決するために研究を重ねたところ、（ａ）式［Ｉ］で表されるポリメトキシフラボン、（ｂ）炭素数３〜８の２価アルコール、（ｃ）式［II］で表されるアルキレンオキシド誘導体を特定の比率で組み合わせることにより、上記の目的とする皮膚化粧料が得られることを見出し、本発明を完成させるに至った。 The inventors of the present invention have made extensive studies in order to solve the above problems. As a result, (a) a polymethoxyflavone represented by the formula [I], (b) a dihydric alcohol having 3 to 8 carbon atoms, (c) The present inventors have found that the target skin cosmetics can be obtained by combining alkylene oxide derivatives represented by the formula [II] at a specific ratio, and have completed the present invention.
すなわち、本発明は以下のとおりである。
（ａ）式［Ｉ］で表されるポリメトキシフラボンを０．０００１〜１質量％、（ｂ）炭素数３〜８の２価アルコールを１〜２５質量％、（ｃ）式［II］で表されるアルキレンオキシド誘導体を１〜１０質量％にて含有する皮膚化粧料。
ＭＧ−[ Ｏ（ＥＯ）ｘ（ＰＯ）ｙ −（ＢＯ）ｚ ]4 ［II］
（式中、ＭＧはメチルグルコシドから水酸基を除いた残基であり、ＥＯはオキシエチレン基であり、ＰＯはオキシプロピレン基であり、ｘおよびｙはそれぞれＥＯおよびＰＯの平均付加モル数であり、０≦ｘ≦２０、１≦ｙ≦１０である。ｘが０でない場合、ＥＯとＰＯがランダム付加し、ＥＯとＰＯとの合計質量に対するＰＯの質量比が１０〜４５質量％である。ＢＯはオキシブチレン基であり、ｚはＢＯの平均付加モル数であり、０≦ｚ≦４である。）
That is, the present invention is as follows.
(A) 0.0001 to 1% by mass of polymethoxyflavone represented by formula [I], (b) 1 to 25% by mass of dihydric alcohol having 3 to 8 carbon atoms, (c) in formula [II] A skin cosmetic containing 1 to 10% by mass of the represented alkylene oxide derivative.
MG- [O (EO) x (PO) y- (BO) z] 4 [II]
(In the formula, MG is a residue obtained by removing a hydroxyl group from methyl glucoside, EO is an oxyethylene group, PO is an oxypropylene group, x and y are average added moles of EO and PO, respectively. 0 ≦ x ≦ 20, 1 ≦ y ≦ 10 When x is not 0, EO and PO are randomly added, and the mass ratio of PO to the total mass of EO and PO is 10 to 45 mass%. Is an oxybutylene group, z is the average added mole number of BO, and 0 ≦ z ≦ 4.)
本発明の皮膚化粧料は、肌のキメを整える効果、毛穴を引き締める効果に優れ、化粧ノリの改善効果、化粧くずれの抑制効果を示すとともに、経時安定性に優れるという効果を奏する。 The skin cosmetic of the present invention is excellent in the effect of adjusting the texture of the skin and the effect of tightening the pores, and exhibits the effect of improving the makeup flakes, the effect of suppressing makeup loss, and being excellent in stability over time.
以下、本発明の実施形態について説明する。
本発明の皮膚化粧料は、下記（ａ）〜（ｃ）成分を含有する。
Hereinafter, embodiments of the present invention will be described.
The skin cosmetic of the present invention contains the following components (a) to (c).
〔（ａ）成分：ポリメトキシフラボン〕
（ａ）成分は式［Ｉ］で表されるポリメトキシフラボンである。
式中、Ｒ１、Ｒ２、Ｒ３はそれぞれ独立して水素原子またはメトキシ基を表す。
本発明の皮膚化粧料の好ましい実施態様においては、以下の式［III］〜式［Ｖ］で示される３，５，６，７，８，３’，４’−ヘプタメトキシフラボン（ヘプタメトキシフラボン）、５，６，７，８，３’，４’−へキサメトキシフラボン（ノビレチン）、５，６，７，８，４’−ペンタメトキシフラボン（タンゲレチン）からなる群から選択される少なくとも１種のポリメトキシフラボンを含有する。
[(A) component: polymethoxyflavone]
The component (a) is a polymethoxyflavone represented by the formula [I].
In the formula, R 1 , R 2 and R 3 each independently represent a hydrogen atom or a methoxy group.
In a preferred embodiment of the skin cosmetic of the present invention, 3,5,6,7,8,3 ', 4'-heptamethoxyflavone (heptamethoxyflavone) represented by the following formulas [III] to [V]: ), 5,6,7,8,3 ′, 4′-hexamethoxyflavone (nobiletin), at least one selected from the group consisting of 5,6,7,8,4′-pentamethoxyflavone (tangeretin) Contains seeds of polymethoxyflavone.
式［Ｉ］で表されるポリメトキシフラボンは、各種の合成法によって得ることができ、植物から天然物として溶媒抽出することによっても得ることができる。
植物から溶媒抽出で得る方法としては、例えば、ミカン科ミカン属植物の果皮から抽出する方法が挙げられる。ミカン科ミカン属植物、例えば、ウンシュウミカン、ポンカン、ハッサク、レモン、タチバナ、ユズ、スダチ、ザボン、タンジェリン、オレンジ、グレープフルーツなどには、ポリメトキシフラボンが含有されている（ Journal of Medicinal Plant Research Vol. ４６, １６２−１６６, （１９８２））。これらの中で、好ましい植物はウンシュウミカン、タチバナ、ユズ、スダチおよびオレンジであり、より好ましい植物はオレンジおよびタチバナである。
The polymethoxyflavone represented by the formula [I] can be obtained by various synthetic methods, and can also be obtained by solvent extraction from plants as a natural product.
As a method of obtaining from a plant by solvent extraction, for example, a method of extracting from the pericarp of a Citrus mandarin plant is mentioned. Citrus mandarin plants, such as Satsuma mandarin, Ponkan, Hassaku, lemon, Tachibana, Yuzu, Sudachi, Pomelo, tangerine, orange, grapefruit, etc. contain polymethoxyflavone (Journal of Medicinal Plant Research Vol. 46, 162-166, (1982)). Among these, preferred plants are Satsuma mandarin, Tachibana, Yuzu, Sudachi and orange, and more preferred plants are orange and Tachibana.
ポリメトキシフラボンの単離精製は、これらのミカン科ミカン属植物の果皮を有機溶剤で抽出し、抽出物をカラムクロマトグラフィーにより分離することにより行なうことができる。以下、具体的に説明する。
まず、ミカン属植物の果皮を水、メタノール、エタノール、プロパノール、ブタノール、プロピレングリコール、１，３−ブチレングリコール等の水溶性アルコール；アセトン、ヘキサン、酢酸エチル、クロロホルム等の溶剤；もしくはそれらの混合溶剤を用いて抽出する。好ましい溶剤は、メタノール、エタノール、プロパノール、ブタノール、プロピレングリコール、１，３−ブチレングリコールおよび酢酸エチルからなる群から選択される１または２以上の溶剤である。より好ましい溶剤は、メタノール、エタノール、プロピレングリコール、１，３−ブチレングリコールおよび酢酸エチルからなる群から選択される１または２以上の溶剤である。
Isolation and purification of polymethoxyflavone can be performed by extracting the peels of these Citrus mandarin plants with an organic solvent and separating the extract by column chromatography. This will be specifically described below.
First, the skin of the mandarin plant is water, methanol, ethanol, propanol, butanol, propylene glycol, 1,3-butylene glycol and other water-soluble alcohols; acetone, hexane, ethyl acetate, chloroform and other solvents; Extract using. Preferred solvents are one or more solvents selected from the group consisting of methanol, ethanol, propanol, butanol, propylene glycol, 1,3-butylene glycol and ethyl acetate. More preferred solvents are one or more solvents selected from the group consisting of methanol, ethanol, propylene glycol, 1,3-butylene glycol and ethyl acetate.
抽出液を濃縮すると目的のポリメトキシフラボンを約１〜１５質量％含有する抽出物が得られる。この抽出物は、さらに乾固してもよい。この抽出物を２倍質量以上、好ましくは３〜１０倍質量の酢酸エチルに溶解し、水を加えて撹拌・分層し、水層を除去してから酢酸エチルを留去して、乾固物を得ることができる。
なお、本発明においては、単離したヘプタメトキシフラボン、ノビレチン、タンゲレチンを単独で添加してもよいし、２種以上混合して用いてもよい。また、合成時の混合物のまま、あるいは植物抽出物等の複数の天然物を含む形態で添加してもよい。
得られた乾固物は、通常、適切な溶剤に再溶解されて液体カラムクロマトグラフィーに供され、ノビレチン、ヘプタメトキシフラボン、タンゲレチンが得られる。液体カラムクロマトグラフィーとしては、シリカゲルまたはアルミナを充填材とし、溶離液として、ヘキサン／エタノールを容積比で７０／３０〜９７／３で混合した混合溶剤が用いられる。
When the extract is concentrated, an extract containing about 1 to 15% by mass of the target polymethoxyflavone is obtained. This extract may be further dried. This extract is dissolved in ethyl acetate having a mass of 2 times or more, preferably 3 to 10 times, and water is added thereto to stir and separate the layers. After removing the aqueous layer, the ethyl acetate is distilled off to dryness. You can get things.
In the present invention, isolated heptamethoxyflavone, nobiletin, and tangeretin may be added alone or in combination of two or more. Moreover, you may add in the form containing several natural products, such as a mixture at the time of a synthesis | combination, or a plant extract.
The obtained dried product is usually redissolved in an appropriate solvent and subjected to liquid column chromatography to obtain nobiletin, heptamethoxyflavone, and tangeretin. For liquid column chromatography, a mixed solvent in which silica gel or alumina is used as a filler and hexane / ethanol is mixed at a volume ratio of 70/30 to 97/3 is used as an eluent.
（ａ）成分の含有量は、皮膚化粧料に対して、０．０００１〜１質量％であり、好ましくは０．０００５〜０．５質量％、さらに好ましくは０．００１〜０．１質量％の割合で含有される。０．０００１質量％未満の場合は、肌のキメを整える効果、毛穴を引き締める効果、化粧ノリの改善効果、化粧くずれの抑制効果が得られ難くなることがある。また、１質量％を超える場合は、含有量に見合った効果が得られ難くなることがある。 (A) Content of component is 0.0001-1 mass% with respect to skin cosmetics, Preferably it is 0.0005-0.5 mass%, More preferably, it is 0.001-0.1 mass%. It is contained in the ratio. If it is less than 0.0001% by mass, it may be difficult to obtain the effect of adjusting the texture of the skin, the effect of tightening the pores, the effect of improving the makeup, and the effect of suppressing makeup loss. Moreover, when it exceeds 1 mass%, the effect corresponding to content may become difficult to be acquired.
〔（ｂ）成分：炭素数３〜８の２価アルコール〕
（ｂ）成分は炭素数３〜８の２価アルコールであり、１分子内に２個の水酸基を有する化合物であり、一般的にグリコール類と称される化合物である。炭素数が３未満の場合は、皮膚に刺激を与えることがあり、炭素数が９以上の場合は、水に対する溶解性が低下することがある。
[(B) component: C3-C8 dihydric alcohol]
The component (b) is a dihydric alcohol having 3 to 8 carbon atoms, a compound having two hydroxyl groups in one molecule, and is a compound generally called glycols. When the number of carbon atoms is less than 3, the skin may be irritated, and when the number of carbon atoms is 9 or more, the solubility in water may decrease.
炭素数３〜８の２価アルコールとして、具体的には、プロピレングリコール、ブチレングリコール、ジエチレングリコール、ペンチレングリコール、へキシレングリコール、ジプロピレングリコール、ヘプチレングリコール、オクチレングリコールなどが挙げられる。中でも使用感等の点で、好ましくは、１，２−プロピレングリコール、１，３−プロピレングリコール、１，３−ブチレングリコール、１，２−ペンチレングリコール、ジプロピレングリコールである。これら２価アルコールのうち１種または２種以上を用いることができる。 Specific examples of the divalent alcohol having 3 to 8 carbon atoms include propylene glycol, butylene glycol, diethylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, heptylene glycol, and octylene glycol. Of these, 1,2-propylene glycol, 1,3-propylene glycol, 1,3-butylene glycol, 1,2-pentylene glycol, and dipropylene glycol are preferable from the viewpoint of usability. One or more of these dihydric alcohols can be used.
（ｂ）成分の含有量は、皮膚化粧料に対して、１〜２５質量％であり、好ましくは５〜１５質量％である。１質量％未満の場合は、肌のキメを整える効果、化粧ノリの改善効果が得られ難くなることがある。また、２５質量％を超える場合は、化粧ノリの改善効果や化粧くずれの抑制効果が得られ難くなることがある。 (B) Content of a component is 1-25 mass% with respect to skin cosmetics, Preferably it is 5-15 mass%. When the amount is less than 1% by mass, it may be difficult to obtain the effect of adjusting the texture of the skin and the effect of improving the makeup. On the other hand, if it exceeds 25% by mass, it may be difficult to obtain the effect of improving the makeup and the effect of suppressing makeup loss.
〔（ｃ）成分：アルキレンオキシド誘導体〕
（ｃ）成分は式［II］で表されるアルキレンオキシド誘導体である。
式中、ＭＧはメチルグルコシドから水酸基を除いた残基であり、ＥＯはオキシエチレン基、ＰＯはオキシプロピレン基、ＢＯはオキシブチレン基である。ｘ、ｙおよびｚは、それぞれＥＯ、ＰＯ、ＢＯの平均付加モル数であり、０≦ｘ≦２０、１≦ｙ≦１０、０≦ｚ≦４を満足し、好ましくは、０≦ｘ≦１０、２≦ｙ≦８、０≦ｚ≦１、さらに好ましくは、ｘ＝０、２≦ｙ≦５、ｚ＝０または７≦ｘ≦８、２≦ｙ≦３、ｚ＝１を満足する。なお、（ＥＯ）ｘ（ＰＯ）ｙ と（ＢＯ）ｚはブロック状に付加している。
ｘが０でない場合、ＥＯとＰＯがランダム付加し、ＥＯとＰＯとの合計質量に対するＰＯの質量比が１０〜４５質量％、好ましくは１５〜４０質量％、さらに好ましくは２０〜３５質量％である。
式［II］で表されるアルキレンオキシド誘導体は、公知の方法により製造することができ、例えば、メチルグルコシドにエチレンオキシドとプロピレンオキシドをランダム状に付加した後、さらにブチレンオキシドを付加することによって得ることができる。なお、オキシブチレン基を与える化合物としては、１，２−ブチレンオキシドが好ましい。
これらアルキレンオキシド誘導体のうち１種または２種以上を用いることができる。
[(C) component: alkylene oxide derivative]
The component (c) is an alkylene oxide derivative represented by the formula [II].
In the formula, MG is a residue obtained by removing a hydroxyl group from methyl glucoside, EO is an oxyethylene group, PO is an oxypropylene group, and BO is an oxybutylene group. x, y, and z are the average added mole numbers of EO, PO, and BO, respectively, satisfying 0 ≦ x ≦ 20, 1 ≦ y ≦ 10, and 0 ≦ z ≦ 4, preferably 0 ≦ x ≦ 10 2 ≦ y ≦ 8, 0 ≦ z ≦ 1, more preferably x = 0, 2 ≦ y ≦ 5, z = 0 or 7 ≦ x ≦ 8, 2 ≦ y ≦ 3, and z = 1. Note that (EO) x (PO) y and (BO) z are added in blocks.
When x is not 0, EO and PO are randomly added, and the mass ratio of PO to the total mass of EO and PO is 10 to 45 mass%, preferably 15 to 40 mass%, more preferably 20 to 35 mass%. is there.
The alkylene oxide derivative represented by the formula [II] can be produced by a known method. For example, it can be obtained by adding ethylene oxide and propylene oxide randomly to methyl glucoside and then adding butylene oxide. Can do. In addition, as a compound which gives an oxybutylene group, 1,2-butylene oxide is preferable.
One or more of these alkylene oxide derivatives can be used.
（ｃ）成分の含有量は、皮膚化粧料に対して、１〜１０質量％であり、好ましくは２〜９質量％、さらに好ましくは３〜５質量％である。１質量％未満の場合は、肌のキメを整える効果、毛穴を引き締める効果、化粧ノリの改善効果、化粧くずれの抑制効果が得られ難くなることがある。また、１０質量％を超える場合は、化粧ノリの改善効果、化粧くずれの抑制効果が得られ難くなることがある。 (C) Content of a component is 1-10 mass% with respect to skin cosmetics, Preferably it is 2-9 mass%, More preferably, it is 3-5 mass%. When the amount is less than 1% by mass, it may be difficult to obtain the effect of adjusting the texture of the skin, the effect of tightening the pores, the effect of improving the makeup, and the effect of suppressing makeup loss. On the other hand, if it exceeds 10% by mass, it may be difficult to obtain the effect of improving the makeup and the effect of suppressing makeup loss.
本発明の皮膚化粧料は、様々な剤型を採ることができ、例えば、化粧液、乳液、ジェル、クリームなどの剤型を採ることができ、さらに、不織布等に含浸させた形態等のいかなる形態であっても良い。
また、本発明の皮膚化粧料には、化粧料や医薬品に常用されている添加剤を、本発明の効果を損なわない範囲で、配合することも可能である。
The skin cosmetics of the present invention can take various dosage forms, such as cosmetic liquids, emulsions, gels, creams, etc., and any form such as a form impregnated with a non-woven fabric. Form may be sufficient.
Moreover, it is also possible to mix | blend the additive normally used for cosmetics and a pharmaceutical in the skin cosmetics of this invention in the range which does not impair the effect of this invention.
以下、実施例および比較例を挙げて本発明をさらに具体的に説明する。
〔実施例１〜８、および比較例１〜５〕
表１に示す配合比率で、以下の方法により皮膚化粧料として化粧液を調製した。
（ａ）成分と（ｂ）成分を混合して、７５〜８５℃に加熱した。さらに、（ｃ）成分、イオン交換水を混合し、７５〜８５℃に加熱した後に冷却して、化粧液を得た。
Hereinafter, the present invention will be described more specifically with reference to examples and comparative examples.
[Examples 1-8 and Comparative Examples 1-5]
A cosmetic liquid was prepared as a skin cosmetic by the following method at the blending ratio shown in Table 1.
The component (a) and the component (b) were mixed and heated to 75 to 85 ° C. Furthermore, (c) component and ion-exchange water were mixed, and it cooled, after heating to 75-85 degreeC, and obtained the cosmetic liquid.
表１中の（ａ）成分（ポリメトキシフラボン）の単離・精製について説明する。
ミカン科オレンジの乾燥果皮１００ｋｇをブレンダーにて粉砕し、５倍質量の９５質量％エタノールで５日間浸漬、抽出した。抽出液を濾過後、減圧濃縮してオレンジ果皮抽出物４５０ｇを得た。このオレンジ果皮抽出物を５倍質量の酢酸エチルに溶解し、酢酸エチルと等量の水を加えて撹拌し、静置後に水層を除去した。この操作を３回繰り返した後、酢酸エチルを留去し、乾固物２８０ｇを得た。
さらに、この乾固物を２倍質量のヘキサン／エタノール混合溶剤（容積比８５／１５）に溶解し、溶解液を得た。シリカゲルを充填したカラム（直径３０ｃｍ、長さ１ｍ）にこの溶解液を全量チャージした。このカラムにカラム容量の２倍容量のヘキサンを流した後、溶離液としてヘキサン／エタノール混合溶剤（容積比９０／１０）を使用し、溶出液を１Ｌずつ分画した。
The isolation and purification of the component (a) in Table 1 (polymethoxyflavone) will be described.
100 kg of dried pericarp orange peel was pulverized with a blender, and immersed and extracted with 5 times mass of 95 mass% ethanol for 5 days. The extract was filtered and concentrated under reduced pressure to obtain 450 g of orange peel extract. This orange peel extract was dissolved in 5-fold mass of ethyl acetate, water equivalent to ethyl acetate was added and stirred, and the aqueous layer was removed after standing. After repeating this operation three times, ethyl acetate was distilled off to obtain 280 g of a dried product.
Further, this dried product was dissolved in a double mass hexane / ethanol mixed solvent (volume ratio 85/15) to obtain a solution. A column (diameter 30 cm, length 1 m) packed with silica gel was charged with the entire amount of the lysate. After flowing hexane of twice the column volume through this column, a hexane / ethanol mixed solvent (volume ratio 90/10) was used as an eluent, and the eluate was fractionated by 1 L.
この各分画液について、展開溶剤としてヘキサン／エタノール混合溶剤（容積比９０／１０）を使用したシリカゲル薄層クロマトグラフに供して分析したところ、式［III］〜式［Ｖ］で示される化合物（ポリメトキシフラボン）の存在を確認した。
そして、それぞれの化合物を含有する分画液を合一してから溶媒を留去し、式［III］〜式［Ｖ］で示される化合物（ポリメトキシフラボン）を得た。
各化合物の収量は、式［IV］の化合物（ノビレチン）が９．２ｇ、式［III］の化合物（ヘプタメトキシフラボン）が１３ｇ、式［Ｖ］の化合物（タンゲレチン）が２．２ｇであった。このようにして、ポリメトキシフラボンが得られた。
なお、表１中では、式［III］の化合物を（ａ）−１成分、式［IV］の化合物を（ａ）−２成分、式［Ｖ］の化合物を（ａ）−３成分と表記する。
Each of these fractions was analyzed by subjecting to a silica gel thin layer chromatograph using a hexane / ethanol mixed solvent (volume ratio 90/10) as a developing solvent. As a result, the compounds represented by the formulas [III] to [V] were analyzed. The presence of (polymethoxyflavone) was confirmed.
Then, the fraction solutions containing the respective compounds were combined, and then the solvent was distilled off to obtain a compound (polymethoxyflavone) represented by the formulas [III] to [V].
The yield of each compound was 9.2 g of the compound of formula [IV] (nobiletin), 13 g of the compound of formula [III] (heptamethoxyflavone), and 2.2 g of the compound of formula [V] (tangeretin). . In this way, polymethoxyflavone was obtained.
In Table 1, the compound of formula [III] is represented as component (a) -1, the compound of formula [IV] as component (a) -2, and the compound of formula [V] as component (a) -3. To do.
（ｃ）−１成分は、式［Ｉ］中におけるｘが０、ｙが２．５、ｚが０のポリオキシプロピレンメチルグルコシドである（商品名：マクビオブライドＭＧ−１０Ｐ、日油株式会社製）。
（ｃ）−２成分は、式［Ｉ］中におけるｘが０、ｙが５、ｚが０のポリオキシプロピレンメチルグルコシドである（商品名：マクビオブライドＭＧ−２０Ｐ、日油株式会社製）。
（ｃ）−３成分は、式［Ｉ］中におけるｘが７、ｙが２、ｚが１であり、ＥＯとＰＯとの合計質量に対するＰＯの質量比が２７．４質量％のポリオキシブチレンポリオキシエチレンポリオキシプロピレンメチルグルコシドである（商品名：ウィルブライドＭＧ−２０７０、日油株式会社製）。
(C) -1 component is polyoxypropylene methyl glucoside in which x in formula [I] is 0, y is 2.5, and z is 0 (trade name: Macbiobride MG-10P, NOF Corporation Made).
(C) -2 component is polyoxypropylene methyl glucoside in which x in formula [I] is 0, y is 5, and z is 0 (trade name: Macbioobride MG-20P, manufactured by NOF Corporation). .
(C) -3 component is polyoxybutylene in which x in formula [I] is 7, y is 2, z is 1, and the mass ratio of PO to the total mass of EO and PO is 27.4% by mass It is polyoxyethylene polyoxypropylene methyl glucoside (trade name: Willbride MG-2070, manufactured by NOF Corporation).
下記５項目について、２０名の女性（３０〜４８歳）をパネラーとし、朝夕の洗顔後、全顔に上記化粧水を塗布することを毎日行ない、１ヶ月後に評価を実施した。下記５項目の評価結果を表１に示す。なお、表１において、評価の項目における括弧内の数字は評価の合計点を示すし、記号は判定内容を示す。 About the following 5 items, 20 females (30 to 48 years old) were panelists, and after the face washing in the morning and evening, the above-mentioned lotion was applied every day, and the evaluation was performed one month later. Table 1 shows the evaluation results of the following five items. In Table 1, the numbers in parentheses in the evaluation items indicate the total points of the evaluation, and the symbols indicate the determination contents.
（１）肌のキメを整える効果
１ヶ月後の肌の状態について、各パネラーが下記のとおりに評価した。
２点：明らかに肌のキメが整ったと感じた場合。
１点：わずかに肌のキメが整ったと感じた場合。
０点：肌のキメが改善しない又はキメが粗くなったと感じた場合。
(1) The effect which prepares the texture of skin Each panelist evaluated the state of the skin after one month as follows.
2 points: When you feel that your skin is clearly textured.
1 point: When the skin feels slightly smooth.
0 point: When the texture of the skin does not improve or the texture feels rough.
２０名のパネラーの合計点を求め、以下のとおりに判定した。
◎：合計点が３５点以上かつ０点が０人：肌のキメを整える効果が非常に高い皮膚化粧料である。
○：合計点が２５点以上３５点未満または合計点が３５点以上かつ０点が１以上２人以下：肌のキメを整える効果が高い皮膚化粧料である。
△：合計点が１５点以上２５点未満：わずかに肌のキメを整える効果を示す皮膚化粧料である。
×：合計点が１５点未満：肌のキメを整える効果が十分でない皮膚化粧料である。
The total score of 20 panelists was calculated and determined as follows.
A: Total score of 35 points or more and 0 points: 0: A skin cosmetic that has a very high effect of adjusting skin texture.
A: The total score is 25 points or more and less than 35 points, or the total score is 35 points or more and the 0 point is 1 or more and 2 or less people: A skin cosmetic with a high effect of adjusting skin texture.
(Triangle | delta): Total score is 15 points or more and less than 25 points: It is skin cosmetics which show the effect which adjusts the texture of skin slightly.
X: The total score is less than 15 points: skin cosmetics that do not have sufficient effect of adjusting skin texture.
（２）毛穴の引き締め効果
１ヶ月後の肌の状態について、マイクロスコープ画像を評価者が肉眼にて観察して、下記のとおりに評価した。
２点：明らかに毛穴が引き締まったと判断した場合。
１点：わずかに毛穴が引き締まったと判断した場合。
０点：毛穴の引き締め効果がないと判断した場合。
(2) Effect of tightening pores With respect to the state of the skin after one month, the evaluator observed the microscope image with the naked eye and evaluated it as follows.
2 points: When it is determined that the pores are clearly tightened.
1 point: When it is determined that the pores are slightly tightened.
0 point: When it is judged that there is no pore tightening effect.
２０名のパネラーについての評価の合計点を求め、以下のとおりに判定した。
◎：合計点が３５点以上かつ０点が０人：毛穴の引き締め効果が非常に優れている皮膚化粧料である。
○：合計点が２５点以上３５点未満または合計点が３５点以上かつ０点が１以上２人以下：毛穴の引き締め効果が優れている皮膚化粧料である。
△：合計点が１５点以上２５点未満：わずかに毛穴の引き締め効果を示す皮膚化粧料である。
×：合計点が１５点未満：毛穴の引き締め効果が十分でない皮膚化粧料である。
The total score of the evaluation for 20 panelists was determined and determined as follows.
A: Total score of 35 points or more and 0 points: 0: Skin cosmetics with excellent pore tightening effect.
A: The total score is 25 points or more and less than 35 points, or the total score is 35 points or more and the 0 point is 1 or more and 2 or less: skin cosmetics with excellent pore tightening effect.
(Triangle | delta): Total score is 15 points or more and less than 25 points: It is skin cosmetics which show the tightening effect of a pore slightly.
X: The total score is less than 15: skin cosmetics with insufficient pore tightening effect.
（３）化粧ノリの改善効果
１ヶ月後、化粧水（皮膚化粧料）を塗布した後、各自が普段使用しているファンデーションを全顔に塗布し、化粧ノリについて、パネラーが下記のとおりに評価した。
２点：化粧ノリが改善したと感じた場合。
１点：わずかに化粧ノリが改善したと感じた場合。
０点：化粧ノリが改善しない又は悪くなったと感じた場合。
(3) Improvement effect of makeup glue One month later, after applying lotion (skin cosmetic), each person's regular foundation is applied to the entire face, and the panelists evaluate the makeup glue as follows. did.
2 points: When the makeup feels improved.
1 point: When the makeup feels slightly improved.
0 point: When the makeup feel is not improved or worsened.
２０名のパネラーについての評価の合計点を求め、以下のとおりに判定した。
◎：合計点が３５点以上かつ０点が０人：化粧ノリの改善効果が非常に優れる皮膚化粧料である。
○：合計点が２５点以上３５点未満または合計点が３５点以上かつ０点が１人以上２人以下：化粧ノリの改善効果が優れる皮膚化粧料である。
△：合計点が１５点以上２５点未満：わずかに化粧ノリの改善効果を示す皮膚化粧料である。
×：合計点が１５点未満：化粧ノリの改善効果が十分でない皮膚化粧料である。
The total score of the evaluation for 20 panelists was determined and determined as follows.
A: Total score of 35 points or more and 0 points: 0: A skin cosmetic with an extremely excellent effect of improving makeup.
◯: Total score of 25 points or more and less than 35 points, or total score of 35 points or more and 0 points of 1 or more and 2 or less: Skin cosmetics with excellent effect of improving makeup.
(Triangle | delta): The total score is 15 points or more and less than 25 points: It is skin cosmetics which show the improvement effect of a makeup | development slightly.
X: The total score is less than 15: It is a skin cosmetic that does not have a sufficient effect of improving makeup flakes.
（４）化粧くずれの抑制効果
１ヶ月後、化粧水（皮膚化粧料）を塗布した後、各自が普段使用しているファンデーションを全顔に塗布し、４時間後の化粧くずれについて、パネラーが下記のとおりに評価した。
２点：化粧くずれが生じにくくなったと感じた場合。
１点：わずかに化粧くずれが生じにくくなったと感じた場合。
０点：化粧くずれが改善しない又は生じると感じた場合。
(4) The effect of suppressing cosmetic breakup After 1 month, after applying lotion (skin cosmetic), each person's usual foundation is applied to the entire face. It evaluated as follows.
2 points: When it is felt that makeup loss is less likely to occur.
1 point: When it feels that makeup loss is hardly caused.
0 point: When it is felt that makeup loss does not improve or occurs.
２０名のパネラーについての評価の合計点を求め、以下のとおりに判定した。
◎：合計点が３５点以上かつ０点が０人：化粧くずれの抑制効果が非常に優れる皮膚化粧料である。
○：合計点が２５点以上３５点未満または合計点が３５点以上かつ０点が１人以上２人以下：化粧くずれの抑制効果が優れる皮膚化粧料である。
△：合計点が１５点以上２５点未満：わずかに化粧くずれの抑制効果を示す皮膚化粧料である。
×：合計点が１５点未満：化粧くずれの抑制効果が十分でない皮膚化粧料である。
The total score of the evaluation for 20 panelists was determined and determined as follows.
A: A total of 35 points or more and 0 points: 0: A skin cosmetic that has a very excellent effect of suppressing makeup loss.
○: Total score is 25 points or more and less than 35 points, or the total score is 35 points or more and 0 point is 1 or more and 2 or less people: skin cosmetics having an excellent effect of suppressing makeup loss.
(Triangle | delta): A total score is 15 points or more and less than 25 points: It is skin cosmetics which show the makeup | decoration effect slightly.
X: The total score is less than 15: skin cosmetics that do not have a sufficient effect of suppressing makeup loss.
（５）経時安定性
化粧水（皮膚化粧料）を透明のガラス容器に密閉して０℃、２５℃、４０℃でそれぞれ３ヶ月間保存したときの状態を肉眼にて観察して、下記の３段階で判定した。
○：安定性良好：（いずれの温度においても外観の変化がなく粒等も生じない。）
△：安定性やや不良（いずれかの温度において僅かに沈殿を生じるか、または僅かに粒が析出している。）
×：安定性不良（いずれかの温度において明らかに沈殿が生じるか、または粒が析出している。）
(5) Stability over time After the skin lotion (skin cosmetic) was sealed in a transparent glass container and stored at 0 ° C., 25 ° C., and 40 ° C. for 3 months, the following conditions were observed. Judgment was made in three stages.
○: Good stability: (No change in appearance at any temperature and no grain or the like)
Δ: Slightly poor (slight precipitation or slight grain precipitation at any temperature)
X: poor stability (precipitation occurs clearly at any temperature, or grains are precipitated)
実施例１〜８の皮膚化粧料（化粧水）は、肌のキメを整える効果、毛穴を引き締める効果、化粧ノリの改善効果、化粧くずれの抑制効果とともに経時安定性が優れていた。
一方、比較例１〜５では十分な性能が得られていない。
具体的には、比較例１では、（ａ）成分のポリメトキシフラボンを含有しないため、肌のキメを整える効果、化粧ノリの改善効果が弱く、毛穴を引き締める効果、化粧くずれの抑制効果が不十分である。
比較例２では、（ｂ）成分の代わりにエタノールを含有するため、肌のキメを整える効果が不十分である。
比較例３では、（ｃ）成分のアルキレンオキシド誘導体を過剰に含有するため、化粧ノリの改善効果や化粧くずれの抑制効果が不十分である。
また比較例４、５では、（ｃ）成分の代わりに、アルキレンオキシド誘導体として、ポリオキシエチレン（２０モル) メチルグルコシドエーテルまたはポリオキシプロピレン（２５モル）ソルビトールを含有するため、化粧ノリの改善効果不十分であり、経時安定性も優れない。
The skin cosmetics (skin lotions) of Examples 1 to 8 were excellent in stability over time as well as the effect of adjusting the texture of the skin, the effect of tightening the pores, the effect of improving makeup flakes, and the effect of suppressing makeup breakage.
On the other hand, in Comparative Examples 1-5, sufficient performance is not obtained.
Specifically, in Comparative Example 1, since it does not contain the component (a) polymethoxyflavone, the effect of adjusting the texture of the skin, the effect of improving the makeup flare is weak, the effect of tightening pores, and the effect of suppressing makeup loss It is enough.
In Comparative Example 2, since ethanol is contained instead of the component (b), the effect of adjusting the texture of the skin is insufficient.
In Comparative Example 3, since the alkylene oxide derivative of the component (c) is excessively contained, the effect of improving the makeup flakes and the effect of suppressing makeup loss are insufficient.
In Comparative Examples 4 and 5, since the polyoxyethylene (20 mol) methyl glucoside ether or polyoxypropylene (25 mol) sorbitol is contained as the alkylene oxide derivative instead of the component (c), the effect of improving the cosmetic paste is improved. Insufficient and stable over time.
〔実施例９および１０〕
表２に示す配合比率で、常法に従って実施例９および１０の水中油型乳液を調製した。なお、表２中の乳液の共通成分Ａを表３に示す。
Examples 9 and 10
The oil-in-water emulsions of Examples 9 and 10 were prepared according to a conventional method at the blending ratio shown in Table 2. Table 3 shows the common component A of the emulsions in Table 2.
〔実施例１１〕
表２に示す配合比率で、常法に従って実施例１１のクリームを調製した。なお、表２中のクリームの共通成分Ｂを表４に示す。
Example 11
The cream of Example 11 was prepared according to a conventional method at the blending ratio shown in Table 2. In addition, Table 4 shows the common component B of the cream in Table 2.
実施例９および１０の乳液、および実施例１１のクリームについて、実施例１〜８と同様に、（１）肌のキメを整える効果、（２）毛穴の引き締め効果、（３）化粧ノリの改善効果、（４）化粧くずれの抑制効果、および（５）経時安定性の評価、判定を行なった。これら５項目の評価結果を表２に示す。 For the emulsions of Examples 9 and 10 and the cream of Example 11, as in Examples 1 to 8, (1) the effect of adjusting the texture of the skin, (2) the effect of tightening the pores, and (3) the improvement of the makeup paste The effect, (4) the effect of suppressing makeup loss, and (5) the stability over time were evaluated and judged. Table 2 shows the evaluation results of these five items.
表２の評価結果に示されるように、実施例９〜１１の皮膚化粧料は、肌のキメを整える効果、毛穴を引き締める効果、化粧ノリの改善効果、化粧くずれの抑制効果を示すとともに、経時安定性に優れる結果が得られた。 As shown in the evaluation results of Table 2, the skin cosmetics of Examples 9 to 11 showed the effect of adjusting the texture of the skin, the effect of tightening the pores, the effect of improving the makeup flakes, and the effect of suppressing makeup breakage, and Results with excellent stability were obtained.
本発明の皮膚化粧料は、肌のキメを整える効果、毛穴を引き締める効果に優れ、連続的に塗布することで、化粧ノリの改善効果、化粧くずれの抑制効果を示すとともに経時安定性に優れる。したがって、本発明の皮膚化粧料は、化粧液、乳液、ジェル、クリームなどの各種の皮膚化粧料として好適に利用することができる。
The skin cosmetic of the present invention is excellent in the effect of adjusting the texture of the skin and the effect of tightening the pores. By continuously applying the skin cosmetic, the effect of improving the makeup flakes and the effect of suppressing makeup loss are exhibited and the stability over time is also excellent. Therefore, the skin cosmetics of the present invention can be suitably used as various skin cosmetics such as cosmetic liquids, emulsions, gels and creams.
Claims (1)
ＭＧ−[ Ｏ（ＥＯ）ｘ（ＰＯ）ｙ −（ＢＯ）ｚ ]4 ［II］
（式中、ＭＧはメチルグルコシドから水酸基を除いた残基であり、ＥＯはオキシエチレン基であり、ＰＯはオキシプロピレン基であり、ｘおよびｙはそれぞれＥＯおよびＰＯの平均付加モル数であり、０≦ｘ≦２０、１≦ｙ≦１０である。ｘが０でない場合、ＥＯとＰＯがランダム付加し、ＥＯとＰＯとの合計質量に対するＰＯの質量比が１０〜４５質量％である。ＢＯはオキシブチレン基であり、ｚはＢＯの平均付加モル数であり、０≦ｚ≦４である。） (A) 0.0001 to 1% by mass of polymethoxyflavone represented by formula [I], (b) 1 to 25% by mass of dihydric alcohol having 3 to 8 carbon atoms, (c) in formula [II] A skin cosmetic containing 1 to 10% by mass of the represented alkylene oxide derivative.
MG- [O (EO) x (PO) y- (BO) z] 4 [II]
(In the formula, MG is a residue obtained by removing a hydroxyl group from methyl glucoside, EO is an oxyethylene group, PO is an oxypropylene group, x and y are average added moles of EO and PO, respectively. 0 ≦ x ≦ 20, 1 ≦ y ≦ 10 When x is not 0, EO and PO are randomly added, and the mass ratio of PO to the total mass of EO and PO is 10 to 45 mass%. Is an oxybutylene group, z is the average added mole number of BO, and 0 ≦ z ≦ 4.)
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017222605A (en) * | 2016-06-15 | 2017-12-21 | 日油株式会社 | Cosmetic composition |
| JP2020172449A (en) * | 2019-04-08 | 2020-10-22 | 日油株式会社 | Gel-like skin cosmetic |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002003363A (en) * | 2000-04-19 | 2002-01-09 | Nof Corp | Cosmetic composition |
| JP2011201820A (en) * | 2010-03-26 | 2011-10-13 | Nippon Menaade Keshohin Kk | Transparent liquid state skin preparation for external use |
| JPWO2011105568A1 (en) * | 2010-02-26 | 2013-06-20 | 小太郎漢方製薬株式会社 | Dried plant tissue and plant tissue extract for improving central nervous degenerative diseases accompanied by learning / memory disorders and movement disorders, and pharmaceuticals and foods containing them |
-
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002003363A (en) * | 2000-04-19 | 2002-01-09 | Nof Corp | Cosmetic composition |
| JPWO2011105568A1 (en) * | 2010-02-26 | 2013-06-20 | 小太郎漢方製薬株式会社 | Dried plant tissue and plant tissue extract for improving central nervous degenerative diseases accompanied by learning / memory disorders and movement disorders, and pharmaceuticals and foods containing them |
| JP2011201820A (en) * | 2010-03-26 | 2011-10-13 | Nippon Menaade Keshohin Kk | Transparent liquid state skin preparation for external use |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017222605A (en) * | 2016-06-15 | 2017-12-21 | 日油株式会社 | Cosmetic composition |
| JP2020172449A (en) * | 2019-04-08 | 2020-10-22 | 日油株式会社 | Gel-like skin cosmetic |
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