JP4288306B2 - Cosmetics containing dimer dilinoleic acid diethylene glycol oligomer ester - Google Patents
Cosmetics containing dimer dilinoleic acid diethylene glycol oligomer ester Download PDFInfo
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- JP4288306B2 JP4288306B2 JP2008516588A JP2008516588A JP4288306B2 JP 4288306 B2 JP4288306 B2 JP 4288306B2 JP 2008516588 A JP2008516588 A JP 2008516588A JP 2008516588 A JP2008516588 A JP 2008516588A JP 4288306 B2 JP4288306 B2 JP 4288306B2
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- acid
- diethylene glycol
- cream
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 title claims description 200
- 239000000539 dimer Substances 0.000 title claims description 61
- 239000002537 cosmetic Substances 0.000 title claims description 47
- 150000002148 esters Chemical class 0.000 title claims description 40
- VJZWIFWPGRIJSN-XRHABHTOSA-N dilinoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O.CCCCC\C=C/C\C=C/CCCCCCCC(O)=O VJZWIFWPGRIJSN-XRHABHTOSA-N 0.000 title claims description 20
- 239000002253 acid Substances 0.000 claims description 45
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 25
- 235000020778 linoleic acid Nutrition 0.000 claims description 24
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 21
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- 235000019192 riboflavin Nutrition 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 229940092258 rosemary extract Drugs 0.000 description 1
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- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
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- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
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- 231100000430 skin reaction Toxicity 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 229940037001 sodium edetate Drugs 0.000 description 1
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- 239000001540 sodium lactate Substances 0.000 description 1
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- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
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- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
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- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019164 vitamin B2 Nutrition 0.000 description 1
- 239000011716 vitamin B2 Substances 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/005—Preparations for sensitive skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/75—Anti-irritant
Description
本発明はダイマージリノール酸ジエチレングリコールオリゴマーエステルを含有する化粧料に関する。 The present invention relates to a cosmetic containing dimer dilinoleic acid diethylene glycol oligomer ester.
近年、環境の変化に伴い、アトピー性皮膚炎などのアレルギー疾患者や、いわゆる敏感肌と感じる人が増加し、これらの人は皮膚が過敏になっているため、化粧品などにより発赤、かゆみといった刺激を感じることが多く、より低刺激な化粧品が求められる。したがって、そのような刺激を緩和する優れた成分を新たに提供することが求められている。
界面活性剤等の皮膚刺激緩和剤として、トレハロースモノ脂肪酸エステル（特許文献１：特開平１０−４５５６０号公報）、パーフルオロアルキル基およびポリオキシアルキレン基を側鎖として持つシリコーン（特許文献２：特開平６−１９９６２９号公報）、アルコール刺激緩和剤として、フェニルエチル−α−グルコシド、フェニルエチル−β−グルコシドのようなグルコース誘導体（特許文献３：特開平８−２８３１２１号公報）、脂溶性薬剤の刺激緩和剤としてポリアルキレングリコール（特許文献４：特開２００２−２１２０２４号公報）、経皮外用剤の刺激緩和剤としてクエン酸トリアルキル、多価アルコール、水（特許文献５：特開平５−２５５１１８号公報）が開示されている。しかしながら、化粧品の基剤として大きな配合比を占める油剤に関しては、安全性に関しては研究されているが（非特許文献１： 杉山、太田、「化粧品油性原料の皮膚刺激性評価」、日皮協ジャーナル、日本産業皮膚衛生協会、１９９９年２月、第４１巻、ｐ．１３６−１４２）、刺激緩和作用については研究されていない。In recent years, with changes in the environment, the number of people with allergic diseases such as atopic dermatitis and those who feel so-called sensitive skin has increased, and these people are sensitive to skin, so redness and itching caused by cosmetics etc. Therefore, cosmetics that are less irritating are required. Therefore, it is required to newly provide an excellent component that relieves such irritation.
As a skin irritation relieving agent such as a surfactant, trehalose monofatty acid ester (Patent Document 1: Japanese Patent Laid-Open No. 10-45560), silicone having a perfluoroalkyl group and a polyoxyalkylene group as side chains (Patent Document 2: Special) Kaihei 6-199629), as an alcohol stimulus mitigating agent, glucose derivatives such as phenylethyl-α-glucoside and phenylethyl-β-glucoside (Patent Document 3: JP-A-8-283121), fat-soluble drugs Polyalkylene glycol as a stimulus-relaxing agent (Patent Document 4: Japanese Patent Laid-Open No. 2002-212024), Trialkyl citrate, polyhydric alcohol, water as a stimulant-relaxing agent for a transdermal external preparation (Patent Document 5: Japanese Patent Laid-Open No. 5-255118) No. Gazette) is disclosed. However, oils that occupy a large blending ratio as cosmetic bases have been studied for safety (Non-patent Document 1: Sugiyama, Ota, “Evaluation of skin irritation of cosmetic oily raw materials”, JCIA Journal. , Japan Industrial Skin Hygiene Association, February 1999, Vol. 41, p.136-142), irritation mitigating action has not been studied.
ダイマー酸のエステルを含有する化粧料に関しては、つや、保水性、感触、皮膚及び毛髪への密着性、感触向上の持続性、毛髪のセット性について検討したものが特許文献６（特開２００４−２７７２８５号公報）に開示されている。特許文献６では、刺激緩和作用は検討されていない。 As for cosmetics containing esters of dimer acid, Patent Document 6 (Japanese Patent Application Laid-Open No. 2004-2000) has been studied on glossiness, water retention, feel, adhesion to skin and hair, sustainability of touch improvement, and hair setting properties. No. 277285). In Patent Document 6, the stimulus relaxation action is not studied.
刺激緩和作用に優れた油剤を見出し、その油剤を含有する化粧料を提供することである。 It is an object of the present invention to find an oil agent having an excellent irritation reducing effect and to provide a cosmetic containing the oil agent.
本発明の主な構成は、次のとおりである。
（１）ダイマージリノール酸ジエチレングリコールオリゴマーエステルを含有する化粧料。
（２）ダイマージリノール酸ジエチレングリコールオリゴマーエステルは、構成するダイマージリノール酸とジエチレングリコールの比率が、ダイマージリノール酸：ジエチレングリコール＝０．５モル：１．０モル〜０．８モル：１．０モルであることを特徴とする
（１）記載の化粧料。
（３）ダイマージリノール酸ジエチレングリコールオリゴマーエステルは、構成するダイマージリノール酸とジエチレングリコールの比率が、ダイマージリノール酸：ジエチレングリコール＝０．５モル：１．０モルであることを特徴とする（１）記載の化粧料。
（４）ダイマージリノール酸ジエチレングリコールオリゴマーエステルの２５℃における粘度が２，５００〜４，５００ｍＰａ・ｓであることを特徴とする（１）記載の化粧料。
（５）ダイマージリノール酸ジエチレングリコールオリゴマーエステルが皮膚刺激緩和成分であること特徴とする（１）〜（４）のいずれかに記載の化粧料。
（６）顔用または身体用の保湿化粧料であることを特徴とする（１）〜（５）のいずれかに記載の化粧料。
（７）ダイマージリノール酸ジエチレングリコールオリゴマーエステルが、５〜２０質量％含有されていることを特徴とする（２）〜（６）のいずれかに記載の化粧料。
（８）構成するダイマージリノール酸とジエチレングリコールの比率が、ダイマージリノール酸：ジエチレングリコール＝０．５モル：１．０モル〜０．８モル：１．０モルであるダイマージリノール酸ジエチレングリコールオリゴマーエステルを含有する化粧料用油剤。The main configuration of the present invention is as follows.
(1) Cosmetics containing dimer dilinoleic acid diethylene glycol oligomer ester.
(2) Dimerlinoleic acid diethylene glycol oligomer ester is composed of dimerlinoleic acid and diethylene glycol in a ratio of dimerlinoleic acid: diethylene glycol = 0.5 mol: 1.0 mol to 0.8 mol: 1.0 mol The cosmetic according to (1), wherein
(3) Dimerlinoleic acid diethylene glycol oligomer ester is characterized in that the ratio of dimerlinoleic acid and diethylene glycol is dimerlinoleic acid: diethylene glycol = 0.5 mol: 1.0 mol (1) Cosmetics described.
(4) The cosmetic composition according to (1), wherein the dimerginolelic acid diethylene glycol oligomer ester has a viscosity of 2,500 to 4,500 mPa · s at 25 ° C.
(5) The cosmetic according to any one of (1) to (4), wherein dimer dilinoleic acid diethylene glycol oligomer ester is a skin irritation reducing component.
(6) The cosmetic according to any one of (1) to (5), which is a moisturizing cosmetic for face or body.
(7) The cosmetic according to any one of (2) to (6), wherein dimerlinoleic acid diethylene glycol oligomer ester is contained in an amount of 5 to 20% by mass.
(8) Dimerlinoleic acid diethylene glycol oligomer ester in which the ratio of dimerlinoleic acid and diethylene glycol is dimerlinoleic acid: diethylene glycol = 0.5 mol: 1.0 mol to 0.8 mol: 1.0 mol An oil for cosmetics containing
１．刺激緩和効果に優れる油剤並びにその油剤を含有する化粧料を提供することができた。
２．本発明の化粧料は刺激緩和効果に優れるので、本発明の化粧料を用いることにより、刺激物質による皮膚のバリア破壊を抑制することができる。バリア破壊の抑制により肌荒れが改善し、皮膚が保護されるので、肌荒れ改善効果・保湿効果に優れる化粧料を提供することができる。
３．本発明の化粧料を用いることにより、皮膚刺激に伴う乾燥から引き起こされる老化に対し、優れた保湿効果により皮膚の健康を維持するので老化を予防できる。
４．本発明の化粧料に用いるダイマージリノール酸ジエチレングリコールオリゴマーエステルは粘性があまり高くなく、べたつき、ぎらつきがあまり強くないので、乳液、クリーム等の保湿用化粧料に好適に用いることができる。1. It was possible to provide an oil agent having an excellent irritation mitigating effect and a cosmetic containing the oil agent.
2. Since the cosmetic of the present invention is excellent in the effect of alleviating irritation, the use of the cosmetic of the present invention can suppress the skin barrier destruction caused by the irritant. Since the rough skin is improved and the skin is protected by suppressing the barrier destruction, it is possible to provide a cosmetic excellent in the rough skin improving effect and the moisturizing effect.
3. By using the cosmetic of the present invention, aging can be prevented because aging caused by drying accompanying skin irritation is maintained due to excellent moisturizing effect.
4). Dimer dilinoleic acid diethylene glycol oligomer ester used in the cosmetics of the present invention is not very high in viscosity and is not very sticky or glaring, so it can be suitably used in moisturizing cosmetics such as emulsions and creams.
以下、本発明の詳細を説明する。
本発明のダイマージリノール酸ジエチレングリコールオリゴマーエステルはダイマージリノール酸とジエチレングリコールをエステル化して得られる。Details of the present invention will be described below.
The dimerged linoleic acid diethylene glycol oligomer ester of the present invention is obtained by esterifying dimerged linoleic acid and diethylene glycol.
＜ダイマージリノール酸＞
ダイマージリノール酸は、一般的にはダイマー酸と呼ばれる２塩基酸で、２分子のリノール酸［(9Z,12Z)-オクタデカ-9,12-ジエン酸］等の不飽和脂肪酸を重合させたリノール酸の２量体である。リノール酸の重合反応の生成物にはリノール酸の２量体の他に、未反応のリノール酸や３量体、さらに高重合のリノール酸重合体が含まれる。分子蒸留によりリノール酸の２量体の含有量を９０質量％以上に高めることができる。また、得られたリノール酸の２量体の不飽和結合に水素を添加して安定化させることができる。これらのリノール酸の２量体を水素添加したものは、一般的には水添ダイマー酸と呼ばれている。本発明のダイマージリノール酸ジエチレングリコールオリゴマーエステルの合成に用いるダイマージリノール酸としては、これらのダイマー酸、及び、水添ダイマー酸の何れをも使用することができるが、酸化安定性の観点から水添ダイマー酸を使用することがより好ましい。水添ダイマー酸は市販品、例えばユニケマ社ＰＲＩＰＯＬ１００６、ＰＲＩＰＯＬ１００９、ＰＲＩＰＯＬ１０２５等を用いることが可能である。<Dimer linoleic acid>
Dimer linoleic acid is a dibasic acid generally called dimer acid, and is a linole obtained by polymerizing unsaturated fatty acids such as two molecules of linoleic acid [(9Z, 12Z) -octadeca-9,12-dienoic acid]. It is a dimer of acid. The product of the polymerization reaction of linoleic acid includes, in addition to the dimer of linoleic acid, unreacted linoleic acid and trimer, and a highly polymerized linoleic acid polymer. The content of the dimer of linoleic acid can be increased to 90% by mass or more by molecular distillation. Moreover, hydrogen can be added to the dimer unsaturated bond of the obtained linoleic acid to stabilize it. A hydrogenated dimer of these linoleic acids is generally called hydrogenated dimer acid. Any of these dimer acids and hydrogenated dimer acids can be used as the dimer linoleic acid used for the synthesis of the diethylene glycol oligomer oligomer ester of the present invention, but from the viewpoint of oxidation stability, water can be used. It is more preferable to use an additive dimer acid. As the hydrogenated dimer acid, commercially available products such as PRIKOL 1006, PRIPOL 1009, PRIPOL 1025, etc. manufactured by Unikema Co., Ltd. can be used.
＜ジエチレングリコール＞
ジエチレングリコールはＯ（ＣＨ２ＣＨ２ＯＨ）２の化学式で表される化合物であり、有機合成原料として市販されている。<Diethylene glycol>
Diethylene glycol is a compound represented by the chemical formula of O (CH 2 CH 2 OH) 2 and is commercially available as an organic synthesis raw material.
ダイマージリノール酸とジエチレングリコールをエステル化反応で重合することによりダイマージリノール酸ジエチレングリコールオリゴマーエステルを得ることができる。エステル化法は特に限定されないが、例えば、無触媒若しくは触媒としてパラトルエンスルホン酸、硫酸、塩酸、メタンスルホン酸等を用いて、無溶媒若しくは溶媒としてトルエン、ヘキサン、ヘプタン等を用いて、５０〜２６０℃の温度で反応すれば良い。 Dimerlinoleic acid diethylene glycol oligomer ester can be obtained by polymerizing dimerlinoleic acid and diethylene glycol by an esterification reaction. Although the esterification method is not particularly limited, for example, paratoluenesulfonic acid, sulfuric acid, hydrochloric acid, methanesulfonic acid or the like is used as a non-catalyst or a catalyst, and toluene, hexane, heptane or the like is used as a solvent-free or solvent. What is necessary is just to react at the temperature of 260 degreeC.
ダイマージリノール酸とジエチレングリコールの構成するダイマージリノール酸とジエチレングリコールの比率は０．５モル：１．０モル〜０．８モル：１．０モルが好ましい。ダイマージリノール酸：ジエチレングリコールの比率が０．５モル：１．０モルのときは、ダイマージリノール酸の両端にジエチレングリコールが結合したものを中心とした分布のオリゴマーとなる。ダイマージリノール酸：ジエチレングリコールの比率が０．８モル：１．０モルのときはダイマージリノール酸４つとジエチレングリコール５つがエステル結合したものを中心とした分布のオリゴマーとなる。
いずれにしてもダイマージリノール酸と比べてジエチレングリコールが過剰なので、カルボキシル基はほとんど残存せず、オリゴマーの末端に残存する官能基はほとんど水酸基となる。ダイマージリノール酸とジエチレングリコールのモル比が１に近づくと重合度が増大し、油剤の粘性が増大し好ましくない。また、ジエチレングリコールと比べてダイマージリノール酸のモル濃度が過剰になると、残存する官能基がカルボキシル基となり、安全性の点で好ましくない。The ratio of dimer linoleic acid and diethylene glycol, which is composed of dimer linoleic acid and diethylene glycol, is preferably 0.5 mol: 1.0 mol to 0.8 mol: 1.0 mol. When the ratio of dimer dilinoleic acid: diethylene glycol is 0.5 mol: 1.0 mol, the oligomer has a distribution centered on dimer diglycol bonded to both ends of dimer dilinoleic acid. When the ratio of dimer linoleic acid: diethylene glycol is 0.8 mol: 1.0 mol, an oligomer having a distribution centering on an ester bond between four dimer linoleic acids and five diethylene glycols is obtained.
In any case, since diethylene glycol is excessive as compared with dimer linoleic acid, the carboxyl group hardly remains, and the functional group remaining at the terminal of the oligomer becomes almost a hydroxyl group. When the molar ratio of dimer linoleic acid and diethylene glycol approaches 1, the degree of polymerization increases and the viscosity of the oil increases, which is not preferable. Further, if the molar concentration of dimer linoleic acid is excessive as compared with diethylene glycol, the remaining functional group becomes a carboxyl group, which is not preferable in terms of safety.
特に、構成するダイマージリノール酸とジエチレングリコールの比率が、ダイマージリノール酸：ジエチレングリコール＝０．５モル：１．０モルであって、２５℃における粘度が２，５００〜４，５００ｍＰａ・ｓであるダイマージリノール酸ジエチレングリコールオリゴマーエステルは、薬物の皮膚浸透性が小さく、刺激緩和作用、経皮水分蒸散抑制作用が認められ、肌荒れ防止効果が高いことが確認できた。この作用は、類似のダイマージリノール酸ジエチレングリコールオリゴマーエステルに比べても、顕著な差があることが確認できた。
なお、特許文献６には、各種のダイマー酸ジエチレングリコールオリゴマーエステルを配合した化粧料について検討されているが、刺激緩和作用は検討されていない。特許文献６には、ダイマー酸ジエチレングリコールオリゴマーエステル（ダイマー酸：ジエチレングリコール＝１：０．５）／混合アルコール（ベヘニルアルコール：イソステアリルアルコール：フィトステロール＝９：１：１）エステルが開示されているが、本願発明の仕込み比率がダイマージリノール酸：ジエチレングリコール＝０．５モル：１．０モル〜０．８モル：１．０モルであるダイマージリノール酸ジエチレングリコールオリゴマーエステルは開示されておらず、極性が異なり、両者は物性、使用性が全く異なる。In particular, the ratio of dimer dilinoleic acid and diethylene glycol is dimer dilinoleic acid: diethylene glycol = 0.5 mol: 1.0 mol, and the viscosity at 25 ° C. is 2,500-4,500 mPa · s. Dimerdilinoleic acid diethylene glycol oligomer ester was found to have a low skin permeability of the drug, an irritation mitigating action and a transdermal moisture transpiration inhibiting action, and a high anti-rough skin effect. It was confirmed that this effect was significantly different from that of the similar dimer dilinoleic acid diethylene glycol oligomer ester.
In addition, although patent document 6 is examining the cosmetics which mix | blended various dimer acid diethylene glycol oligomer ester, the irritation | stimulation mitigation effect | action is not examined. Patent Document 6 discloses dimer acid diethylene glycol oligomer ester (dimer acid: diethylene glycol = 1: 0.5) / mixed alcohol (behenyl alcohol: isostearyl alcohol: phytosterol = 9: 1: 1) ester. Dimer linoleic acid diethylene glycol oligomer ester in which the charge ratio of the invention is dimer linoleic acid: diethylene glycol = 0.5 mol: 1.0 mol to 0.8 mol: 1.0 mol is not disclosed, and the polarity is different Both are completely different in physical properties and usability.
本発明の化粧料に配合するダイマージリノール酸ジエチレングリコールオリゴマーエステルの配合量は必ずしも制限されないが、化粧料全量に対し、０．１〜９５質量%が好ましい。化粧料が保湿化粧料の場合にはダイマージリノール酸ジエチレングリコールオリゴマーエステルの配合量は０．１〜４０質量％が好ましく、５〜２０質量％が特に好ましい。４０質量％以上だと、べたつきが強すぎて保湿化粧料にあまり適さない。２０質量％以上だとべたつきが大きい。５質量％以下であると刺激緩和作用が弱くなり、０．１質量％以下では刺激緩和作用が殆ど認められない。 Although the compounding quantity of the dimer dilinoleic acid diethylene glycol oligomer ester mix | blended with the cosmetics of this invention is not necessarily restrict | limited, 0.1-95 mass% is preferable with respect to cosmetics whole quantity. When the cosmetic is a moisturizing cosmetic, the amount of dimer dilinoleic acid diethylene glycol oligomer ester is preferably 0.1 to 40% by mass, particularly preferably 5 to 20% by mass. If it is 40% by mass or more, the stickiness is too strong and it is not suitable for moisturizing cosmetics. If it is 20% by mass or more, stickiness is large. When the amount is 5% by mass or less, the stimulus relaxation effect is weakened, and when the amount is 0.1% by mass or less, the stimulus relaxation effect is hardly recognized.
本発明の化粧料（医薬部外品を含む）としてはローション、乳液、スキンクリーム、ハンドクリーム、ボディミルク、美容液、サンスクリーン剤、リキッドファンデーション、口紅等が挙げられる。本発明の化粧料は、顕著な刺激緩和効果及び肌荒れ防止効果を有するので、保湿化粧料に適している。保湿化粧料としてはローション、乳液、スキンクリーム、ハンドクリーム、ボディミルク、美容液等が挙げられる。 Examples of the cosmetics (including quasi-drugs) of the present invention include lotions, emulsions, skin creams, hand creams, body milks, serums, sunscreen agents, liquid foundations, lipsticks and the like. The cosmetic of the present invention has a remarkable irritation mitigating effect and a rough skin preventing effect, and is therefore suitable for a moisturizing cosmetic. Examples of moisturizing cosmetics include lotions, emulsions, skin creams, hand creams, body milks, and beauty serums.
本発明の化粧料には、その用途、使用目的、剤形などに応じて、植物油のような油脂類、高級脂肪酸、高級アルコール、アニオン界面活性剤、カチオン界面活性剤、両性界面活性剤、非イオン界面活性剤、防腐剤、糖類、金属イオン封鎖剤、粉体成分、紫外線吸収剤、紫外線遮断剤、ヒアルロン酸のような保湿剤、香料、ｐＨ調整剤等を含有させることができる。ビタミン類、皮膚賦活剤、血行促進剤、常在菌コントロール剤、活性酸素消去剤、抗炎症剤、美白剤、殺菌剤等の他の薬効成分、生理活性成分を含有させることもできる。 The cosmetics of the present invention include fats and oils such as vegetable oils, higher fatty acids, higher alcohols, anionic surfactants, cationic surfactants, amphoteric surfactants, non-active substances, depending on the use, purpose of use, dosage form, etc. Ionic surfactants, preservatives, saccharides, sequestering agents, powder components, UV absorbers, UV blockers, humectants such as hyaluronic acid, fragrances, pH adjusters, and the like can be included. Vitamins, skin activators, blood circulation promoters, resident bacteria control agents, active oxygen scavengers, anti-inflammatory agents, whitening agents, bactericides, and other medicinal and physiologically active components can also be included.
油脂類としては、例えば、ツバキ油、月見草油、マカデミアナッツ油、オリーブ油、ナタネ油、トウモロコシ油、ゴマ油、ホホバ油、胚芽油、小麦胚芽油、トリオクタン酸グリセリン等の液体油脂、カカオ脂、ヤシ油、硬化ヤシ油、パーム油、パーム核油、モクロウクロウ核油、硬化油、硬化ヒマシ油等の固体油脂、ミツロウ、キャンデリラロウ、綿ロウ、ヌカロウ、ラノリン、酢酸ラノリン、液状ラノリン、サトウキビロウ等のロウ類、流動パラフィン、スクワレン、スクワラン、マイクロクリスタリンワックス等があげられる。
高級脂肪酸として、例えば、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、オレイン酸、リノール酸、リノレン酸、ドコサヘキサエン酸（ＤＨＡ）、エイコサペンタエン酸（ＥＰＡ）等があげられる。Examples of the fats and oils include camellia oil, evening primrose oil, macadamia nut oil, olive oil, rapeseed oil, corn oil, sesame oil, jojoba oil, germ oil, wheat germ oil, glycerin trioctanoate, cocoa butter, coconut oil, Solid oils such as hydrogenated coconut oil, palm oil, palm kernel oil, brown owl kernel oil, hydrogenated oil, hydrogenated castor oil, wax such as beeswax, candelilla wax, cotton wax, nutca wax, lanolin, lanolin acetate, liquid lanolin, sugarcane wax And liquid paraffin, squalene, squalane, microcrystalline wax and the like.
Examples of higher fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, docosahexaenoic acid (DHA), and eicosapentaenoic acid (EPA).
高級アルコールとして、例えば、ラウリルアルコール、ステアリルアルコール、セチルアルコール、セトステアリルアルコール等の直鎖アルコール、モノステアリルグリセリンエーテル、ラノリンアルコール、コレステロール、フィトステロール、オクチルドデカノール等の分枝鎖アルコール等があげられる。 Examples of the higher alcohol include linear alcohols such as lauryl alcohol, stearyl alcohol, cetyl alcohol, and cetostearyl alcohol, and branched chain alcohols such as monostearyl glycerin ether, lanolin alcohol, cholesterol, phytosterol, and octyldodecanol.
アニオン界面活性剤として、例えば、ラウリン酸ナトリウム等の脂肪酸塩、ラウリル硫酸ナトリウム等の高級アルキル硫酸エステル塩、ＰＯＥラウリル硫酸トリエタノールアミン等のアルキルエーテル硫酸エステル塩、Ｎ−アシルサルコシン酸、スルホコハク酸塩、Ｎ−アシルアミノ酸塩等があげられる。
カチオン界面活性剤として、例えば、塩化ステアリルトリメチルアンモニウム等のアルキルトリメチルアンモニウム塩、塩化ベンザルコニウム、塩化ベンゼトニウム等があげられる。Examples of the anionic surfactant include fatty acid salts such as sodium laurate, higher alkyl sulfates such as sodium lauryl sulfate, alkyl ether sulfates such as POE lauryl sulfate triethanolamine, N-acyl sarcosine acid, sulfosuccinate N-acyl amino acid salts and the like.
Examples of the cationic surfactant include alkyltrimethylammonium salts such as stearyltrimethylammonium chloride, benzalkonium chloride, and benzethonium chloride.
両性界面活性剤として、例えば、アルキルベタイン、アミドベタイン等のベタイン系界面活性剤等があげられる。
非イオン界面活性剤として、例えば、ソルビタンモノオレエート等のソルビタン脂肪酸エステル類、硬化ヒマシ油誘導体があげられる。
防腐剤として、例えば、メチルパラベン、エチルパラベン等をあげることができる。
金属イオン封鎖剤として、例えば、エチレンジアミン四酢酸二ナトリウム、エデト酸、エデト酸ナトリウム塩等のエデト酸塩をあげることができる。
べたつきを抑えたり、色を付けたりするために、粉末成分として、例えば、タルク、カオリン、雲母、シリカ、ゼオライト、ポリエチレン粉末、ポリスチレン粉末、セルロース粉末、無機白色顔料、無機赤色系顔料、酸化チタンコーテッドマイカ、酸化チタンコーテッドタルク、着色酸化チタンコーテッドマイカ等のパール顔料、赤色２０１号、赤色２０２号等のタール色素をあげることができる。Examples of amphoteric surfactants include betaine surfactants such as alkyl betaines and amide betaines.
Examples of nonionic surfactants include sorbitan fatty acid esters such as sorbitan monooleate, and hardened castor oil derivatives.
Examples of preservatives include methyl paraben and ethyl paraben.
Examples of the sequestering agent include edetate such as disodium ethylenediaminetetraacetate, edetic acid, and sodium edetate.
In order to suppress stickiness and color, powder components include, for example, talc, kaolin, mica, silica, zeolite, polyethylene powder, polystyrene powder, cellulose powder, inorganic white pigment, inorganic red pigment, titanium oxide coated Mention may be made of pearl pigments such as mica, titanium oxide coated talc and colored titanium oxide coated mica, and tar dyes such as red 201 and red 202.
紫外線吸収剤として、例えば、パラアミノ安息香酸、サリチル酸フェニル、パラメトキシケイ皮酸イソプロピル、パラメトキシケイ皮酸オクチル、２，４−ジヒドロキシベンゾフェノン等をあげることができる。
紫外線遮断剤として、例えば、酸化チタン、タルク、カルミン、ベントナイト、カオリン、酸化亜鉛等をあげることができる。Examples of the ultraviolet absorber include paraaminobenzoic acid, phenyl salicylate, isopropyl paramethoxycinnamate, octyl paramethoxycinnamate, 2,4-dihydroxybenzophenone, and the like.
Examples of the ultraviolet blocking agent include titanium oxide, talc, carmine, bentonite, kaolin, and zinc oxide.
保湿剤として、例えば、キシリトール、マルチトール、マルトース、ソルビトール、ブドウ糖、果糖、ショ糖、乳糖、コンドロイチン硫酸ナトリウム、ヒアルロン酸ナトリウム、乳酸ナトリウム、ピロリドンカルボン酸、シクロデキストリン等があげられる。
薬効成分として、例えば、ビタミンＡ油、レチノール等のビタミンＡ類、リボフラビン等のビタミンＢ2類、ピリドキシン塩酸塩等のＢ6類、パントテン酸カルシウム等のパントテン酸類、ビタミンＤ2、コレカルシフェロール等のビタミンＤ類、α−トコフェロール、酢酸トコフェロール、ニコチン酸ＤＬ−α−トコフェロール等のビタミンＥ類等のビタミン類をあげることができる。Examples of the humectant include xylitol, maltitol, maltose, sorbitol, glucose, fructose, sucrose, lactose, sodium chondroitin sulfate, sodium hyaluronate, sodium lactate, pyrrolidone carboxylic acid, cyclodextrin and the like.
Medicinal ingredients include, for example, vitamin A oils such as vitamin A oil and retinol, vitamin B2 such as riboflavin, B6 such as pyridoxine hydrochloride, pantothenic acids such as calcium pantothenate, vitamin D2 such as vitamin D2 and cholecalciferol And vitamins such as vitamin E such as α-tocopherol, tocopherol acetate, and DL-α-tocopherol nicotinate.
そのほかに、ローヤルゼリー、ぶなの木エキス等の皮膚賦活剤、カプサイシン、ジンゲロン、カンタリスチンキ、イクタモール、カフェイン、タンニン酸、γ−オリザノール等の血行促進剤、グリチルリチン酸誘導体、グリチルレチン酸誘導体、アズレン等の消炎剤、アルギニン、セリン、ロイシン、トリプトファン等のアミノ酸類、常在菌コントロール剤のマルトースショ糖縮合物、塩化リゾチーム等をあげることができる。
さらに、カミツレエキス、パセリエキス、ワイン酵母エキス、グレープフルーツエキス、スイカズラエキス、コメエキス、ブドウエキス、ホップエキス、コメヌカエキス、ビワエキス、オウバクエキス、ヨクイニンエキス、センブリエキス、メリロートエキス、バーチエキス、シャクヤクエキス、サボンソウエキス、ヘチマエキス、トウガラシエキス、レモンエキス、ゲンチアナエキス、シソエキス、アロエエキス、ローズマリーエキス、セージエキス、タイムエキス、茶エキス、海藻エキス、キューカンバーエキス、チョウジエキス、マロニエエキス、ハマメリスエキス、クワエキス等の各種抽出物を配合することができる。In addition, skin activators such as royal jelly and beech tree extract, capsaicin, gingeron, cantalis tincture, ictamol, caffeine, tannic acid, γ-oryzanol and other blood circulation promoters, glycyrrhizic acid derivatives, glycyrrhetinic acid derivatives, azulene, etc. Anti-inflammatory agents, amino acids such as arginine, serine, leucine and tryptophan, maltose sucrose condensate of resident bacteria control agent, lysozyme chloride and the like.
In addition, chamomile extract, parsley extract, wine yeast extract, grapefruit extract, honeysuckle extract, rice extract, grape extract, hop extract, rice bran extract, loquat extract, buckwheat extract, yakuinin extract, assembly extract, merilot extract, birch extract, peonies extract, savonso Extract, loofah extract, red pepper extract, lemon extract, gentian extract, perilla extract, aloe extract, rosemary extract, sage extract, thyme extract, tea extract, seaweed extract, cucumber extract, clove extract, maronier extract, hamamelis extract, mulberry extract, etc. Various extracts can be blended.
ダイマージリノール酸ジエチレングリコールオリゴマーエステル（ダイマージリノール酸：ジエチレングリコール＝０．５モル：１．０モル）を実施例１とし、その製造を示す。
攪拌機、温度計、ガス導入管を備えた１Ｌの反応器に、ダイマージリノール酸（ユニケマ社製、ＰＲＩＰＯＬ１０２５）３４９ｇ（０．６モル）及びジエチレングリコール１２７ｇ（１．２モル）を仕込み、窒素気流中２１０〜２２０℃に加熱し、生成する水を留去しながら１２時間エステル化反応を行い、ダイマージリノール酸ジエチレングリコールオリゴマーエステル（ダイマージリノール酸：ジエチレングリコール＝０．５：１．０）（以下「ＤＥＧ−ＤＡ５」と表すことがある）４１６ｇを淡黄色高粘度油状物として得た。
得られた３ロットの油剤の物性値を以下表１に示す。Dimer dilinoleic acid diethylene glycol oligomer ester (dimer dilinoleic acid: diethylene glycol = 0.5 mol: 1.0 mol) is taken as Example 1, and its production is shown.
Into a 1 L reactor equipped with a stirrer, a thermometer, and a gas introduction tube was charged 349 g (0.6 mol) of dimer linoleic acid (manufactured by Unikema, PRIPOL 1025) and 127 g (1.2 mol) of diethylene glycol in a nitrogen stream. It is heated to 210-220 ° C., and the esterification reaction is carried out for 12 hours while distilling off the generated water, and dimerlinoleic acid diethylene glycol oligomer ester (dimermarinoleic acid: diethylene glycol = 0.5: 1.0) (hereinafter “ 416 g) (sometimes referred to as “DEG-DA5”) as a pale yellow, highly viscous oil.
The physical properties of the obtained 3 lots of oil are shown in Table 1 below.
ダイマージリノール酸ジエチレングリコールオリゴマーエステル（ダイマージリノール酸：ジエチレングリコール＝０．８モル：１．０モル）を実施例２とし、その製造を示す。
攪拌機、温度計、ガス導入管を備えた１Ｌの反応器に、ダイマージリノール酸（ユニケマ社製、ＰＲＩＰＯＬ１０２５）３７２ｇ（０．６４モル）及びジエチレングリコール８４．８ｇ（０．８モル）を仕込み、窒素気流中２１０〜２２０℃に加熱し、生成する水を留去しながら１４時間エステル化反応を行い、ダイマージリノール酸ジエチレングリコールオリゴマーエステル（ダイマージリノール酸：ジエチレングリコール＝０．８：１．０）（以下「ＤＥＧ−ＤＡ８」と表すことがある）３７５ｇを淡黄色高粘度油状物として得た。
得られた油剤の物性値を以下表２に示す。Dimer dilinoleic acid diethylene glycol oligomer ester (dimer dilinoleic acid: diethylene glycol = 0.8 mol: 1.0 mol) is taken as Example 2 and its production is shown.
A 1 L reactor equipped with a stirrer, a thermometer, and a gas introduction tube was charged with 372 g (0.64 mol) of dimerlinoleic acid (manufactured by Unikema, PRIPOL 1025) and 84.8 g (0.8 mol) of diethylene glycol, and nitrogen. It is heated to 210-220 ° C. in an air stream, and the esterification reaction is carried out for 14 hours while distilling off the generated water, and dimerlinoleic acid diethylene glycol oligomer ester (dimerlinoleic acid: diethylene glycol = 0.8: 1.0) ( In the following, 375 g (sometimes referred to as “DEG-DA8”) was obtained as a pale yellow high-viscosity oil.
The physical properties of the obtained oil are shown in Table 2 below.
＜薬物皮膚浸透試験＞
実施例１の油剤と市販のダイマー酸エステル、ダイマージオールエステルの薬物皮膚浸透性を評価した。
１．試料
表３に示す実施例１で得られた油剤（ＤＥＧ−ＤＡ５）及び市販のダイマー酸エステル、ダイマージオールエステルに、１％となるようイブプロフェン（Ｓｉｇｍａ）を溶解した試料を用いて、薬物皮膚浸透試験を実施した。 <Drug skin penetration test>
The drug skin permeability of the oil agent of Example 1 and commercially available dimer acid ester and dimer diol ester was evaluated.
1. Sample Drug skin penetration using a sample obtained by dissolving ibuprofen (Sigma) to 1% in the oil agent (DEG-DA5) obtained in Example 1 shown in Table 3 and a commercially available dimer acid ester or dimer diol ester. The test was conducted.
２．試験方法
−８０℃に冷凍保存されたＹｕｃａｔａｎ Ｍｉｃｒｏｐｉｇ背部皮膚（５ヵ月齢雌性、日本チャールスリバー（株））を室温で３０分間解凍し、皮膚についた余分な脂肪を取り除いた後、約２cm四方に切断し試験に用いた。
有効面積０．９５cm２で皮膚をセルにはさみ、試料０．２mlを塗布した。４８時間後に皮膚表面の試料を拭き取りにより除去し、皮膚をメタノール／０．１%リン酸水溶液混液（７０：３０）中で鋏およびホモジナイザーを用いて破砕してイブプロフェンを抽出し、皮膚中のイブプロフェン量をＨＰＬＣにて測定した。測定結果を表３に示す。
２．１ ＨＰＬＣ測定条件
検出器：紫外吸光光度計ＬＣ−１０ＡＤ（（株）島津製作所 製）
測定波長：２２０ｎｍ
カラム：ＴＳＫ−ＧＥＬ ＯＤＳ−８０Ｔｓ ４．６mm×１５０mm（東ソ（株））
移動相：メタノール：０．１％リン酸水溶液＝ ７５：２５
流 速：１ｍｌ／分
２．２ データ処理
ＣＬＡＳＳ−ＶＰ（島津製作所（株）製）を用い、イブプロフェンのピーク面積から別に検量線を作成し、計算により濃度を求めた。2. Test Method Yucatan Micropig dorsal skin (5-month-old female, Nippon Charles River Co., Ltd.) frozen at -80 ° C. for 30 minutes at room temperature to remove excess fat on the skin, about 2 cm square Cut and used for testing.
The skin was sandwiched between cells with an effective area of 0.95 cm 2 and 0.2 ml of sample was applied. After 48 hours, the skin surface sample was removed by wiping, and the skin was crushed in a methanol / 0.1% phosphoric acid aqueous solution mixture (70:30) using an acupuncture and homogenizer to extract ibuprofen, and ibuprofen in the skin was extracted. The amount was measured by HPLC. Table 3 shows the measurement results.
2.1 HPLC measurement conditions Detector: UV absorptiometer LC-10AD (manufactured by Shimadzu Corporation)
Measurement wavelength: 220 nm
Column: TSK-GEL ODS-80Ts 4.6 mm × 150 mm (Tosoh Corporation)
Mobile phase: methanol: 0.1% aqueous phosphoric acid solution = 75:25
Flow rate: 1 ml / min 2.2 Data processing CLASS-VP (manufactured by Shimadzu Corporation) was used to create another calibration curve from the peak area of ibuprofen, and the concentration was determined by calculation.
３．結果
測定結果を表３に示す。
イブプロフェンは経皮吸収性の指標として一般的に用いる。イブプロフェンの皮膚への吸収が少なければ、刺激物質の吸収を抑制する効果に優れる。
実施例１の油剤（ＤＥＧ−ＤＡ５）にイブプロフェンを溶解した場合、４８時間後の皮膚中のイブプロフェン量が２１μｇなのに対して、市販のダイマー酸エステル、ダイマージオールエステルの場合、イブプロフェン量は３７μｇ〜７０μｇであった。ダイマー酸エステル、ダイマージオールエステルの中でも実施例１の油剤（ＤＥＧ−ＤＡ５）は極めてイブプロフェンの皮膚浸透を抑制する効果に優れ、刺激物質の吸収抑制効果に優れている。市販油剤の中でもLUSPLAN DD-DHR：日本精化(株)製 ダイマージリノレイル水添ロジン縮合物 （イブプロフェン量３７μｇ）、LUSPLAN DD-DA7：日本精化(株)製 ダイマージリノール酸ダイマージリノレイル（イブプロフェン量４２μｇ）もイブプロフェンの吸収量が低いほうであるが、両油剤とも粘性が高く、べたつきがつよく、ぎらつくので、保湿化粧料に用いることは困難である。3. Results Table 3 shows the measurement results.
Ibuprofen is generally used as an index for transdermal absorption. If absorption of ibuprofen into the skin is small, the effect of suppressing the absorption of stimulating substances is excellent.
When ibuprofen was dissolved in the oil of Example 1 (DEG-DA5), the amount of ibuprofen in the skin after 48 hours was 21 μg, whereas in the case of commercially available dimer acid ester and dimer diol ester, the amount of ibuprofen was 37 μg to 70 μg. Met. Among the dimer acid ester and dimer diol ester, the oil agent (DEG-DA5) of Example 1 is extremely excellent in the effect of suppressing ibuprofen skin permeation and is excellent in the absorption suppression effect of the stimulant substance. Among commercial oils, LUSPLAN DD-DHR: Nihon Seika Co., Ltd. dimer linoleyl hydrogenated rosin condensate (ibuprofen amount 37 μg), LUSPLAN DD-DA7: Nihon Seika Co., Ltd. dimer linoleic acid dimer dilino Rail (ibuprofen amount 42 μg) also has a lower absorption of ibuprofen, but both oils are highly viscous, sticky, and glaring, making it difficult to use in moisturizing cosmetics.
＜コラーゲンゲル法を用いた刺激緩和性試験＞
実施例１で調製した油剤（ＤＥＧ−ＤＡ５）、実施例２で調製した油剤（ＤＥＧ−ＤＡ８）と市販の油剤の刺激緩和作用を比較した。
１．被験物質
表４に示す油剤をそのまま、あるいは動物やヒトで刺激性があると報告されているラウリン酸を油剤中に０．５質量％、０．８質量％、１．２質量％添加して被験物質とした。< Irritation relaxation test using collagen gel method>
The stimulant mitigating action of the oil agent (DEG-DA5) prepared in Example 1 and the oil agent (DEG-DA8) prepared in Example 2 and a commercially available oil agent were compared.
1. Test substance The oil agent shown in Table 4 is added as it is, or 0.5% by mass, 0.8% by mass and 1.2% by mass of lauric acid, which is reported to be irritating in animals and humans, are added to the oil agent. The test substance was used.
２．試験方法
２．１ コラーゲンゲルの作製
タイプＩ−ＡＣコラーゲン（高研）水溶液と正常ヒト線維芽細胞（CAMBLEX製）の培地中懸濁液、並びに適量の再構築液をスターラーで混合して調製し、タイプＩ−ＡＣコラーゲン（高研）の最終濃度０．１質量％、正常ヒト線維芽細胞（CAMBLEX製）の最終濃度４．０×１０５ｃｅｌｌｓ／ｍＬとして、６ｗｅｌｌカルチャーインサート（ＦＡＬＣＯＮ製）に１ｍＬ滴下した。培養培地はＤＭＥＭ＋１０％ＦＢＳを用いた。コラーゲンゲルを、約１６時間（１２時間〜２４時間）培養した。
２．２ 被験物質のコラーゲンゲルへの適用
２．１で作製したコラーゲンゲル上にラウリン酸０．５質量％、０．８質量％、１．２質量％添加および無添加の被験物質を１ｇ添加し、２４時間暴露させた。２４時間暴露後、被験物質を除去しＭＴＴａｓｓａｙによる細胞生存率を測定・算出し、細胞生存率のラウリン酸濃度依存性を調べた。2. Test Method 2.1 Preparation of Collagen Gel Prepare a mixture of type I-AC collagen (Koken) aqueous solution, normal human fibroblasts (manufactured by CAMBLEX) in a medium, and an appropriate amount of reconstituted solution with a stirrer. The final concentration of type I-AC collagen (Koken) is 0.1% by mass, the final concentration of normal human fibroblasts (CAMBLEX) is 4.0 × 10 5 cells / mL, and the 6-well culture insert (manufactured by FALCON) is used. 1 mL was added dropwise. The culture medium was DMEM + 10% FBS. The collagen gel was cultured for about 16 hours (12-24 hours).
2.2 Application of test substance to collagen gel Add 0.5g, 0.8%, 1.2% by weight of lauric acid and 1g of test substance without addition to the collagen gel prepared in 2.1 And exposed for 24 hours. After the exposure for 24 hours, the test substance was removed, and the cell viability by MTTassay was measured and calculated, and the dependence of the cell viability on the lauric acid concentration was examined.
３．結果
結果を表４に示す。
ダイマージリノール酸ジエチレングリコールオリゴマーエステル（ダイマージリノール酸：ジエチレングリコール＝０．５：１．０）はラウリン酸を１．２質量％添加したものでも細胞生存率は約８０％であり、刺激緩和効果に極めて優れることが分かった。ラウリン酸無添加よりも、ラウリン酸０．５％添加のほうが細胞生存率が向上しているデータがあるが（実施例１で調製した油剤(DEG-DA5)で９５％→１０４％、LUSPLAN DD-ISで７２％→７８％）、これはデータのばらつきによる。3. Results The results are shown in Table 4.
Dimer dilinoleic acid diethylene glycol oligomer ester (dimer dilinoleic acid: diethylene glycol = 0.5: 1.0) has a cell viability of about 80% even when 1.2% by mass of lauric acid is added, which is effective in reducing the stimulation. It turned out to be very good. There is data that the cell viability is improved by adding 0.5% lauric acid compared with no addition of lauric acid (95% → 104% for oil preparation (DEG-DA5) prepared in Example 1), LUSPLAN DD -72% → 78% for IS), due to data variability.
＜細胞を用いた刺激緩和性試験＞
ラウリル硫酸ナトリウムを添加したクリームを正常ヒト線維芽細胞に適用し、クリームがラウリル硫酸ナトリウムの刺激を緩和する効果を調べた。
１．被験クリーム
表５に示された処方のクリームである実施例３、比較例１、比較例２のクリームを用い、各クリーム、並びに、それらのクリームに１０％ラウリル硫酸ナトリウム水溶液を添加混合し、クリーム中のラウリル硫酸ナトリウムの含有量を０．１％に調整したものを用いた。 <Irritation relaxation test using cells>
A cream supplemented with sodium lauryl sulfate was applied to normal human fibroblasts, and the effect of the cream on mitigating the stimulation of sodium lauryl sulfate was examined.
1. Test Cream Using the creams of Example 3, Comparative Example 1 and Comparative Example 2 which are creams having the formulation shown in Table 5, each cream and a 10% sodium lauryl sulfate aqueous solution were added to and mixed with the creams. The content of sodium lauryl sulfate was adjusted to 0.1%.
２．試験方法
被験クリームを培地に混合希釈した。
正常ヒト線維芽細胞を９６穴プレートに３．５×１０３播種し、５日間培養した。
コンフルエントの状態で、被験クリームの濃度が０．１５６％〜２０％となるように混合希釈した培地に交換し、細胞を被験クリームに暴露させた。
２０時間暴露後ＭＴＴアッセイ法を用いて細胞生存率を求めた。2. Test Method The test cream was mixed and diluted in the medium.
Normal human fibroblasts were seeded in a 96-well plate at 3.5 × 10 3 and cultured for 5 days.
In a confluent state, the medium was changed to a mixed and diluted medium so that the concentration of the test cream was 0.156% to 20%, and the cells were exposed to the test cream.
Cell viability was determined using MTT assay after 20 hours exposure.
３．結果
ラウリル硫酸ナトリウムを含有しないクリームを各種濃度で細胞に暴露したときの生存率を図１に、０．１％の濃度でラウリル硫酸ナトリウムを含有させたクリームを各種濃度で細胞に暴露したときの生存率を図２に示す。
図１に示すように、各例ともラウリル硫酸ナトリウムを含有しないクリームを各種濃度で細胞に暴露したとき、培地中のクリームの濃度が０．１５６％から２０％に増大するにつれて、生存率は約８０％から約６０％にほぼ同様に低下した。
一方、図２に示すように、０．１％の濃度でラウリル硫酸ナトリウムを含有させたクリームを各種濃度で細胞に暴露したとき、培地中のクリームの濃度を０．１５６％から１０％まで増大させても、各例とも細胞生存率は約８０％から約７０％にほぼ同様に低下する程度であった。
しかしながら、培地中のクリームの濃度を２０％にすると０．１％の濃度でラウリル硫酸ナトリウムを含有させた実施例３のクリームは５４％の細胞生存率を維持したが、０．１％の濃度でラウリル硫酸ナトリウムを含有させた比較例１及び２のクリームでは細胞が殆ど死滅した（細胞生存率１％）。
従って、実施例３のクリームはラウリル硫酸ナトリウムの刺激を緩和する効果が特に優れている。3. Results Fig. 1 shows the survival rate when a cream containing no sodium lauryl sulfate was exposed to cells at various concentrations, and when a cream containing sodium lauryl sulfate at a concentration of 0.1% was exposed to cells at various concentrations. The survival rate is shown in FIG.
As shown in FIG. 1, in each case, when the cream containing no sodium lauryl sulfate was exposed to cells at various concentrations, as the concentration of the cream in the medium increased from 0.156% to 20%, the survival rate was about It decreased almost similarly from 80% to about 60%.
On the other hand, as shown in FIG. 2, when the cream containing sodium lauryl sulfate at a concentration of 0.1% was exposed to cells at various concentrations, the concentration of the cream in the medium increased from 0.156% to 10%. Even in this case, the cell viability in each case decreased from about 80% to about 70% almost similarly.
However, when the concentration of the cream in the medium was 20%, the cream of Example 3 containing sodium lauryl sulfate at a concentration of 0.1% maintained a cell viability of 54%, but the concentration of 0.1% In the creams of Comparative Examples 1 and 2 containing sodium lauryl sulfate, the cells were almost killed (cell survival rate 1%).
Therefore, the cream of Example 3 is particularly excellent in reducing the irritation of sodium lauryl sulfate.
＜ヒトパッチテストによる刺激緩和性試験＞
実施例１の油剤、実施例１の油剤を配合したクリーム（実施例３とする）、流動パラフィン、流動パラフィンを配合したクリーム（比較例１）について、ラウリル硫酸ナトリウムの刺激を緩和する効果をヒトパッチテストにて評価した。
１．前処理被験品
実施例１の油剤、流動パラフィン並びに表５の組成の実施例３、比較例１のクリームをパッチテスト被験品を適用する前に皮膚に塗布した。
２．パッチテスト被験品
０．５％ラウリル硫酸ナトリウム水溶液と滅菌水（対照）をパッチテスト被験品とした。< Irritation mitigation test by human patch test>
The effect of alleviating the irritation of sodium lauryl sulfate with respect to the oil of Example 1, the cream containing the oil of Example 1 (referred to as Example 3), the liquid paraffin, and the cream containing liquid paraffin (Comparative Example 1) Evaluated by patch test.
1. Pre-treated test product The oil of Example 1, liquid paraffin, and the cream of Example 3 and Comparative Example 1 having the composition shown in Table 5 were applied to the skin before applying the patch test test product.
2. Patch test test article A 0.5% sodium lauryl sulfate aqueous solution and sterilized water (control) were used as patch test test articles.
３．被験者
過去のパッチテストにおいてラウリル硫酸ナトリウム０．１〜０．５％水溶液で擬陽性反応以上を示し、貼付部位にかゆみ、かぶれなどの皮膚症状がでていない、健康な２０〜５０代の１２名（男３名、女９名）を用いた。
４．試験方法
前処理被験品を塗布し、その後、パッチテスト被験品を検体とした２４時間閉塞貼付試験を行った。被験者の上腕内側部にあらかじめ１０ｍｍ×３０ｍｍの範囲を片腕３箇所および２箇所（両腕で５箇所）マーキングし、各箇所の経皮水分蒸散量をＤｅｌｆｉｎ製ｖａｐｏｍｅｔｅｒを用いて測定した。次に、前処理被験品４品を１箇所ずつ１０μＬ塗布し５〜１０分程度なじませた（残り１箇所は前処理被験品無塗布）。前処理被験品が皮膚になじんだことを確認後、パッチテスト被験品約２０μＬを人体貼付試験用フィンチャンバー（直径１１ｍｍ大正製薬）上の濾紙に滴下し、直ちに被験者の５箇所のマーキング箇所に２２時間閉塞貼付した。フィンチャンバーを除去して、２時間後（貼付２４時間後）および翌日２４時間後（貼付４８時間後）に表６に示す判定基準に従って、皮膚反応を目視観察した。同時に経皮水分蒸散量を測定した。3. Subjects Twelve healthy 20 to 50 generations who showed a false positive reaction or higher with a 0.1% to 0.5% aqueous solution of sodium lauryl sulfate in a past patch test and did not show skin symptoms such as itching and rash on the applied site ( 3 males and 9 females) were used.
4). Test Method A pretreated test product was applied, and then a 24-hour occlusion patch test was performed using the patch test test product as a specimen. An area of 10 mm × 30 mm was marked in advance on the inner side of the upper arm of the subject at 3 and 2 locations (5 locations on both arms), and the transdermal moisture transpiration at each location was measured using a Delfin vapometer. Next, 10 μL of 4 pretreated test products were applied one by one and allowed to blend for about 5 to 10 minutes (the remaining 1 site was not applied with the pretreated test product). After confirming that the pre-treated test product became familiar with the skin, about 20 μL of the patch test test product was dropped on the filter paper on the fin chamber for human body sticking test (diameter 11 mm, Taisho Pharmaceutical Co., Ltd.), and immediately on the 5 marking locations of the test subject. Time occlusion was applied. After removing the fin chamber, the skin reaction was visually observed according to the criteria shown in Table 6 at 2 hours (24 hours after application) and 24 hours after the next day (48 hours after application). At the same time, the amount of transdermal moisture transpiration was measured.
５．目視判定結果
目視判定結果を表７に示す。
前処理被験品無塗布の場合、０．５％ラウリル硫酸ナトリウム水溶液貼付２４時間後の皮膚刺激評点平均値０．７５０であるが、前処理被験品を塗布することにより、皮膚刺激評点平均値が低減する。特に、実施例１の油剤（０．２０８）、実施例３のクリーム（０．１６７）は刺激緩和効果が顕著であり、前処理被験品無塗布と比べて皮膚刺激評点平均値が２／１０〜３／１０に低減している。比較例１のクリーム（０．４５８）は、前処理被験品無塗布と比べて６／１０であり刺激緩和効果が認められるが、流動パラフィン（０．６６７）は、前処理被験品無塗布と比べて９／１０であり、刺激緩和効果は殆ど認められない。5. Visual determination results Table 7 shows the visual determination results.
In the case of no pretreatment test article application, the skin irritation score average value 0.750 24 hours after application of a 0.5% sodium lauryl sulfate aqueous solution, but by applying the pretreatment test article, the skin irritation score average value is To reduce. In particular, the oil agent of Example 1 (0.208) and the cream of Example 3 (0.167) have a significant irritation mitigating effect, and the skin irritation score average value is 2/10 as compared to the pretreatment test article non-application. It is reduced to ~ 3/10. The cream of Comparative Example 1 (0.458) was 6/10 compared to the pre-treated test article non-applied and the irritation mitigating effect was observed, but the liquid paraffin (0.667) Compared to 9/10, the stimulus relaxation effect is hardly recognized.
前処理被験品無塗布の場合、０．５％ラウリル硫酸ナトリウム水溶液貼付４８時間後の皮膚刺激評点平均値は１．０８３である。前処理被験品塗布効果については、実施例１の油剤（０．３３３）は前処理被験品無塗布と比べて３／１０であり、顕著な刺激緩和効果が認められる。実施例３のクリーム（０．５８３）は前処理被験品無塗布と比べて５／１０であり、刺激緩和効果が認められる。比較例１のクリーム（０．７９２）は前処理被験品無塗布と比べて７／１０であり、弱いながらも刺激緩和効果が認められる。一方、流動パラフィンを塗布した場合には皮膚刺激評点平均値が１．２９２であり、前処理被験品無塗布と比べて１２／１０であり、ラウリル硫酸ナトリウムの刺激をやや増強する結果である。
実施例１の油剤、並びに実施例１の油剤を配合した実施例３のクリームが顕著な刺激緩和作用を有することが確認できた。In the case where the pretreatment test product was not applied, the skin irritation score average value 48 hours after application of a 0.5% sodium lauryl sulfate aqueous solution was 1.083. About the pretreatment test article application effect, the oil agent (0.333) of Example 1 is 3/10 as compared with the pretreatment test article non-application, and a significant irritation mitigating effect is recognized. The cream of Example 3 (0.583) is 5/10 compared to the pretreated test article non-applied, and an irritation mitigating effect is observed. The cream of Comparative Example 1 (0.792) is 7/10 compared to the pretreatment test article non-application, and although it is weak, an irritation mitigating effect is recognized. On the other hand, when liquid paraffin is applied, the average value of the skin irritation score is 1.292, which is 12/10 as compared to the case where the pretreated test article is not applied, which is a result of slightly enhancing the stimulation of sodium lauryl sulfate.
It was confirmed that the oil agent of Example 1 and the cream of Example 3 containing the oil agent of Example 1 had a significant irritation mitigating action.
６．経皮水分蒸散量測定結果
経皮水分蒸散量測定結果を表７に示す。
前処理被験品無塗布の場合、０．５％ラウリル硫酸ナトリウム水溶液貼付２４時間後の経皮水分蒸散量は８である。滅菌水を貼付したときの経皮水分蒸散量は３であり、それと比べて明らかに皮膚バリアが破壊され、肌荒れが進んでいることがわかる。実施例１の油剤、実施例３のクリームを事前に塗布することにより、０．５％ラウリル硫酸ナトリウム水溶液貼付２４時間後の経皮水分蒸散量はそれぞれ５及び４であり、前処理被験品無塗布８の約半分に抑制される。
従って、刺激緩和効果及び肌荒れ防止効果が発揮されている。比較例１のクリームを事前に塗布した場合、０．５％ラウリル硫酸ナトリウム水溶液貼付２４時間後の経皮水分蒸散量は７であり、前処理被験品無塗布８と殆ど変わらず、刺激緩和効果及び肌荒れ防止効果が殆ど認められない。流動パラフィンを事前に塗布した場合は、０．５％ラウリル硫酸ナトリウム水溶液貼付２４時間後の経皮水分蒸散量は１１であり、前処理被験品無塗布８の約１．４倍であり、皮膚刺激並びに肌荒れが増強されている。6). Table 7 shows the results of measuring the amount of transdermal moisture transpiration.
In the case where the pretreatment test product was not applied, the transdermal moisture transpiration amount was 24 hours after application of the 0.5% sodium lauryl sulfate aqueous solution. The amount of transdermal moisture transpiration when sterilized water is applied is 3, which clearly indicates that the skin barrier is destroyed and the rough skin is progressing. By applying the oil of Example 1 and the cream of Example 3 in advance, the transdermal moisture transpiration after 24 hours of application of the 0.5% sodium lauryl sulfate aqueous solution was 5 and 4, respectively, and there was no pre-treated test article. It is suppressed to about half of the coating 8.
Therefore, the stimulus relaxation effect and the rough skin prevention effect are exhibited. When the cream of Comparative Example 1 was applied in advance, the transdermal moisture transpiration amount after 24 hours of application of the 0.5% sodium lauryl sulfate aqueous solution was 7, which is almost the same as that of the pretreated test article 8 without application, and the irritation mitigating effect. And the effect of preventing rough skin is hardly recognized. When liquid paraffin was applied in advance, the transdermal moisture transpiration amount after 24 hours of application of a 0.5% sodium lauryl sulfate aqueous solution was 11, which is about 1.4 times that of the pretreatment test article 8 without application. Irritation and rough skin are enhanced.
前処理被験品無塗布の場合、０．５％ラウリル硫酸ナトリウム水溶液貼付４８時間後の経皮水分蒸散量は１２に増大し、肌荒れが進行している。実施例１の油剤、実施例３のクリームを事前に塗布することにより、０．５％ラウリル硫酸ナトリウム水溶液貼付４８時間後の経皮水分蒸散量はどちらも４であり、前処理被験品無塗布１２の１／３である。そして、前処理被験品無塗布、滅菌水貼付４８時間後の経皮水分蒸散量２との差が小さい。従って、肌荒れは進行せず軽微であり、肌荒れが顕著に抑制されている。比較例１のクリームを事前に塗布した場合、０．５％ラウリル硫酸ナトリウム水溶液貼付４８時間後の経皮水分蒸散量は８であり、前処理被験品無塗布１２の２／３である。肌荒れ防止効果が認められるが、実施例１の油剤、実施例３のクリームほど顕著ではない。流動パラフィンを事前に塗布した場合は、０．５％ラウリル硫酸ナトリウム水溶液貼付４８時間後の経皮水分蒸散量は１５であり、前処理被験品無塗布１２の約１．３倍であり、皮膚刺激並びに肌荒れが増強されている。 In the case where the pretreatment test product was not applied, the transdermal moisture transpiration amount after 48 hours of application of the 0.5% sodium lauryl sulfate aqueous solution increased to 12, and the rough skin progressed. By applying the oil agent of Example 1 and the cream of Example 3 in advance, the transdermal moisture transpiration after 48 hours of application of a 0.5% sodium lauryl sulfate aqueous solution was 4, and the pretreatment test product was not applied. 1/3 of 12. And the difference with the amount 2 of percutaneous water transpiration | evaporation 48 hours after no pre-processing test article application | coating and sterilization water sticking is small. Accordingly, the rough skin does not proceed and is slight, and the rough skin is remarkably suppressed. When the cream of Comparative Example 1 was applied in advance, the amount of transdermal moisture transpiration 48 hours after application of the 0.5% sodium lauryl sulfate aqueous solution was 8, which was 2/3 of the pretreated test article non-applied 12. Although the rough skin prevention effect is recognized, it is not so remarkable as the oil agent of Example 1 and the cream of Example 3. When liquid paraffin was applied in advance, the transdermal moisture transpiration amount after 48 hours of application of 0.5% sodium lauryl sulfate aqueous solution was 15, which was about 1.3 times that of the pretreated test article 12 without application. Irritation and rough skin are enhanced.
実施例１の油剤、並びに実施例１の油剤を配合した実施例３のクリームが顕著な刺激緩和作用及び肌荒れ防止効果を有することが確認できた。 It was confirmed that the oil agent of Example 1 and the cream of Example 3 containing the oil agent of Example 1 had a significant irritation mitigating action and rough skin prevention effect.
＜アトピー性皮膚炎または皮脂欠乏症を有する男性２０名のパッチテストによる刺激緩和効果試験＞
実施例１の油剤（ＤＥＧ−ＤＡ５）、ＤＥＧ−ＤＡ５を配合したクリームのアトピー性皮膚炎または皮脂欠乏症の被験者に対する刺激緩和効果をヒトパッチテストにて検証した。 <Irritation mitigation effect test by patch test of 20 men with atopic dermatitis or sebum deficiency>
The effect of alleviating the irritation to subjects with atopic dermatitis or sebum deficiency of the cream containing the oil agent (DEG-DA5) and DEG-DA5 of Example 1 was verified by a human patch test.
１．被験者
１−１ 年齢構成
１９歳〜４５歳までの男性２０例で平均年齢は２７．９歳であった。試験途中の脱落はなかった。
１−２ 被験者の皮膚疾患
事前に試験担当医師が被験者の症状について診断した。アトピー性皮膚炎１１例、皮脂欠乏症９例であった。アトピー性皮膚炎疾患の被験者は軽症が７例、軽症〜中等症が２例、中等症が２例であった。1. Subject 1-1 Age Composition Twenty men from 19 to 45 years old had an average age of 27.9 years. There was no dropout during the test.
1-2 Subject skin disease The doctor in charge of the diagnosis made a diagnosis of the subject's symptoms in advance. There were 11 cases of atopic dermatitis and 9 cases of sebum deficiency. The subjects with atopic dermatitis had 7 mild cases, 2 mild to moderate cases, and 2 moderate cases.
２．前処理被験品
実施例１の油剤および実施例１の油剤を配合したクリーム３種、比較例として化粧品用油剤として一般的に使用される流動パラフィンとスクワランを配合したクリーム４種及び皮膚科で処方される保湿剤の代表としてワセリンを前処理被験品とした。無処理を対照とした。
１．ＤＥＧ−ＤＡ５を２０％配合した実施例３のクリーム
２．ＤＥＧ−ＤＡ５を１０％配合した実施例４のクリーム
３．ＤＥＧ−ＤＡ５を５％配合した実施例５のクリーム
４．流動パラフィンを２０％配合した比較例１のクリーム
５．流動パラフィンを１０％配合した比較例３のクリーム
６．スクワランを２０％配合した比較例２のクリーム
７．スクワランを１０％配合した比較例４のクリーム
８．実施例１の油剤（ＤＥＧ−ＤＡ５）
９．ワセリン（日興リカ製）
１０．無処理 （対照）
実施例３、比較例１、２のクリームの処方は表５に示した。実施例４、５、比較例３、４のクリームの処方を表８に示す。2. Pre-treatment test product Three creams containing the oil agent of Example 1 and the oil agent of Example 1, four creams containing liquid paraffin and squalane generally used as cosmetic oils as a comparative example, and prescription in dermatology Vaseline was used as a pretreated test product as a representative humectant. No treatment was the control.
1. 1. Cream of Example 3 containing 20% DEG-DA5 2. The cream of Example 4 containing 10% DEG-DA5. 3. Cream of Example 5 containing 5% DEG-DA5 4. Cream of Comparative Example 1 containing 20% liquid paraffin 5. Cream of Comparative Example 3 containing 10% liquid paraffin 6. Cream of Comparative Example 2 containing 20% squalane. 7. Cream of Comparative Example 4 containing 10% squalane. Oil agent of Example 1 (DEG-DA5)
9. Vaseline (manufactured by Nikko Rica)
10. No treatment (control)
The cream formulations of Example 3 and Comparative Examples 1 and 2 are shown in Table 5. Table 8 shows the formulations of the creams of Examples 4 and 5 and Comparative Examples 3 and 4.
前処理剤の安全性試験
前処理剤の安全性確認試験のため２４時間クローズドパッチテストを実施した。貼付した４被験物質［ＤＥＧ−ＤＡ５配合２０％クリーム（実施例３）、流動パラフィン２０％配合クリーム（比較例１）、スクワラン２０％配合クリーム（比較例２）、ワセリン］の目視評価結果を表１２に示した。ＤＥＧ−ＤＡ５配合クリームや流動パラフィン配合クリームが各判定時間で全陰性の結果に対し、スクワラン配合クリームでスコア３を示した被験者が２４ｈ判定で１名、ワセリンではスコア１を示した被験者が２４ｈで１名認めた。しかし、４８ｈ、7日目では刺激反応が低減しており、アレルギー症状ではないことが確認できた。以上の結果より、４被験物質は、２４ｈ閉塞貼付結果、明らかな一次皮膚刺激性はないことが確認できた。 Pretreatment agent safety test A 24-hour closed patch test was conducted for the safety confirmation test of the pretreatment agent. Table 4 shows visual evaluation results of 4 test substances affixed [DEG-DA5 blended 20% cream (Example 3), liquid paraffin 20% blended cream (Comparative Example 1), squalane 20% blended cream (Comparative Example 2), petrolatum]. This is shown in FIG. In contrast to the results of all negative results for DEG-DA5 cream and liquid paraffin cream in each judgment time, one test subject showed a score of 3 for squalane cream combination, 24 hours for test subjects who showed a score of 1 for petrolatum. One person was admitted. However, the irritation response decreased on the 7th day at 48 h, and it was confirmed that it was not an allergic symptom. From the above results, it was confirmed that the 4 test substances had no apparent primary skin irritation as a result of 24 h occlusion pasting.
３．パッチテスト被験品
皮膚一次刺激の緩和効果を評価するため、皮膚刺激物質として０．５％ラウリル硫酸ナトリウム（関東化学）水溶液（以下、ＳＬＳと呼ぶ）をパッチテスト被験品とした。各塗布部には、対照としてそれぞれ滅菌水を同時に貼付した。3. Patch Test Test Article In order to evaluate the effect of alleviating primary skin irritation, a 0.5% sodium lauryl sulfate (Kanto Chemical) aqueous solution (hereinafter referred to as SLS) was used as a skin test substance as a patch test test article. As a control, sterilized water was simultaneously attached to each application part.
４．変法クローズドパッチテスト試験方法
被験者の背部にプラスチック枠を用いて１０ｍｍ×３０ｍｍの領域を１０箇所設定し、実施例１の油剤（ＤＥＧ−ＤＡ５）、ワセリン並びに実施例３〜５、比較例１〜４のクリームの一定量（約１５μＬ）を微量分注器で量り採り、１箇所に１種類の前処理被験品を塗布した。前処理被験品塗布領域は９箇所であり、残りの１箇所は対照として無処理区とした。
その後、皮膚刺激物質である０．５％ラウリル硫酸ナトリウム水溶液（ＳＬＳ）および対照の滅菌水をパッチテスト被験品として２４時間クローズドパッチテストを実施した。パッチテストには大正製薬のフィンチャンバーを使用した。
塗布部は背骨を挟んで左右5箇所を選択した。塗布部は試験担当医師が被験者の背部を所見し、紅斑等の炎症部位は避けて前処理被験品塗布、パッチ絆貼付を行った。4). Modified Closed Patch Test Test Method Ten regions of 10 mm × 30 mm were set on the back of the subject using a plastic frame, and the oil agent (DEG-DA5), petrolatum of Examples 1 and Examples 3-5, Comparative Examples 1 to A certain amount (about 15 μL) of the cream of 4 was weighed with a micro-dispensing device, and one kind of pretreated test product was applied to one place. There were nine pretreated test article application areas, and the remaining one area was untreated as a control.
Thereafter, a closed patch test was carried out for 24 hours using 0.5% sodium lauryl sulfate aqueous solution (SLS), which is a skin irritant, and sterilized control water as a patch test article. A Taisho Pharmaceutical fin chamber was used for the patch test.
The application part was selected at five locations on the left and right sides of the spine. In the application area, the doctor in charge of the examination looked at the back of the subject and applied the pretreated test article and applied the patch bond while avoiding the inflamed area such as erythema.
５．評価項目と評価時期
以下の２項目を評価した。
１) 皮膚所見： パッチテストによる皮膚変化の目視判定（試験２日目、３日目、７日目）
２) 理学検査： vapometer（Delfin）による経表皮水分蒸散量（試験２日目、３日目）5. Evaluation items and evaluation time The following two items were evaluated.
1) Skin findings: Visual determination of skin changes by patch test (Test Day 2, Day 3, Day 7)
2) Physical examination: Transepidermal water transpiration with vapometer (Delfin) (Test Day 2, Day 3)
６．評価方法
６．１ 皮膚所見
目視判定は皮膚刺激判定基準（表９）に準じて試験担当医師が行った。判定結果は評点にかえ平均値を算出した。得られた値を無塗布部、ワセリン塗布部と比較して有効性を判断した。6). Evaluation method 6.1 Skin findings Visual judgment was performed by the doctor in charge of the test according to the criteria for skin irritation (Table 9). Judgment results were calculated as average values instead of scores. The effectiveness was judged by comparing the obtained values with the uncoated part and the petrolatum coated part.
６．２ 理学検査
vapometerを用いて得られた経表皮水分蒸散量測定値は、各パッチ絆貼付部位より無貼付部位値を差し引いた値を解析に用いた。それぞれの被験物質塗布部の値と無塗布部、ワセリン塗布部と比較して、有効性を判断した。6.2 Physical examination
The transepidermal moisture transpiration measurement value obtained using the vapometer was obtained by subtracting the non-applied site value from each patch adhesive applied site for analysis. The effectiveness was judged by comparing the value of each test substance application part, the non-application part, and the petrolatum application part.
７．皮膚科医による目視判定
貼付２４時間後、４８時間後、７日目に皮膚刺激基準に従って試験担当医師が目視判定した。貼付２４時間後の目視判定結果を表１０に、貼付４８時間後の目視判定結果を表１１に示す。図３、図４に各前処理剤における２０名の０．５％ラウリル硫酸ナトリウム水溶液（ＳＬＳ）皮膚刺激スコアのうち、皮膚刺激基準スコア３、４だけを抜粋し、２４時間後、４８時間後の総和人数を示した。皮膚刺激基準スコアが４を超える被験者はいなかった。
２４時間判定では、無塗布部位と比較してＤＥＧ−ＤＡ５塗布部位（実施例１）、ＤＥＧ−ＤＡ５ ２０％配合クリーム（実施例３）塗布部位で明らかに目視評価スコア３，４以上を示した被験者が少なく、次いでＤＥＧ−ＤＡ５ １０％配合クリーム（実施例４）、ＤＥＧ−ＤＡ５ ５％配合クリーム（実施例５）であった。ワセリンは０．５％ラウリル硫酸ナトリウム水溶液（ＳＬＳ）貼付による目視評価スコア３，４以上を示した被験者が５人と無塗布部位の１２人と比較すると、少ない結果となったが、ＤＥＧ−ＤＡ５およびＤＥＧ−ＤＡ５配合クリームと比較するとその人数は多かった。ＤＥＧ−ＤＡ５配合はスコア１以上の合計点数として見ると全体的に刺激が緩和されていることが認められ、さらに、前述のように刺激が強いスコア３以上も少ないことが認められる。
Wilcoxon符号付順位和検定の結果、ＤＥＧ−ＤＡ５塗布部位（実施例１）、ＤＥＧ−ＤＡ５ ２０％配合クリーム（実施例３）塗布部位、ＤＥＧ−ＤＡ５ １０％クリーム（実施例４）塗布部位でワセリン塗布部位と比較して有為にスコアが低い結果となった（p<0.05）。ＤＥＧ−ＤＡ５ ５％配合クリーム（実施例５）では抑制傾向はみられたものの有為差はなかった。また、ＤＥＧ−ＤＡ５ ２０％配合クリーム（実施例３）は、流動パラフィン２０％配合クリーム（比較例１）、スクワラン２０％配合クリーム（比較例２））と比較して有意に刺激スコアが抑制されていた。さらに、ＤＥＧ−ＤＡ５ １０％配合クリーム（実施例４）は、流動パラフィン１０％配合クリーム（比較例３）、スクワラン１０％配合クリーム（比較例４）と比較して有意に刺激スコアが抑制されていた。7). Visual determination by dermatologist The doctor in charge of the test visually determined on the 7th day after 24 hours and 48 hours after application according to the skin irritation criteria. Table 10 shows the results of visual judgment 24 hours after application, and Table 11 shows the results of visual judgment 48 hours after application. 3 and 4 show only the skin irritation reference scores 3 and 4 out of the 20 0.5% sodium lauryl sulfate aqueous solution (SLS) skin irritation scores in each pretreatment agent, 24 hours and 48 hours later. The total number of people. None of the subjects had a skin irritation reference score greater than 4.
In the 24-hour judgment, compared with the non-application site, DEG-DA5 application site (Example 1), DEG-DA5 20% combination cream (Example 3) clearly showed a visual evaluation score of 3, 4 or more at the application site. The number of subjects was small, followed by DEG-DA5 10% cream (Example 4) and DEG-DA5 5% cream (Example 5). Petrolatum had fewer results when compared to 5 subjects and 12 subjects who had not applied the sample, with a visual evaluation score of 3 or 4 or higher when 0.5% sodium lauryl sulfate aqueous solution (SLS) was applied. DEG-DA5 Compared with the cream containing DEG-DA5, the number was large. When the DEG-DA5 formulation is viewed as a total score of score 1 or higher, it is recognized that the stimulation is alleviated as a whole, and further, as described above, it is recognized that the score of 3 or higher is strong.
As a result of Wilcoxon signed rank sum test, petrolatum was applied at DEG-DA5 application site (Example 1), DEG-DA5 20% combination cream (Example 3) application site, and DEG-DA5 10% cream (Example 4) application site. The score was significantly lower than the application site (p <0.05). In the DEG-DA5 5% combination cream (Example 5), although there was a tendency to suppress, there was no significant difference. Moreover, the stimulation score of DEG-DA5 20% combination cream (Example 3) is significantly suppressed compared to 20% liquid paraffin combination cream (Comparative Example 1) and squalane 20% combination cream (Comparative Example 2)). It was. Furthermore, DEG-DA5 10% combination cream (Example 4) has a significantly suppressed irritation score compared to 10% liquid paraffin combination cream (Comparative Example 3) and squalane 10% combination cream (Comparative Example 4). It was.
４８時間判定では、無塗布部位と比較してＤＥＧ−ＤＡ５塗布部位、ＤＥＧ−ＤＡ５ ５％配合クリーム（実施例５）塗布部位で明らかに目視評価スコア３，４以上を示した被験者が少なく、次いでＤＥＧ−ＤＡ５ ２０％配合クリーム（実施例３）、流動パラフィン２０％配合クリーム（比較例１）であった。ワセリンはＳＬＳ貼付による目視評価スコア３，４以上を示した被験者が８人と無塗布部位の１５人と比較すると、少ない結果となったが、ＤＥＧ−ＤＡ５およびＤＥＧ−ＤＡ５配合クリームと比較するとその人数は多かった。
Wilcoxon符号付順位和検定の結果、ＤＥＧ−ＤＡ５塗布部位（実施例１）、ＤＥＧ−ＤＡ５ ２０％配合クリーム（実施例３）塗布部位、ＤＥＧ−ＤＡ５ ５％クリーム（実施例５）塗布部位でワセリン塗布部位と比較して有為にスコアが低い結果となった（p<0.05）。また、ＤＥＧ−ＤＡ５ ２０％配合クリーム（実施例３）はスクワラン２０％配合クリーム（比較例２）と比較して有意に刺激スコアが抑制されていた（p<0.05）。
７日目判定は、アレルギー症状の有無を確認するために実施した。その結果、スコア１以上を示した被験者は１名のみで無塗布部のSLS貼付部位であり、前処理剤の影響はなかった。In the 48-hour determination, compared with the non-application site, DEG-DA5 application site, DEG-DA5 5% combination cream (Example 5) fewer subjects clearly showed a visual evaluation score of 3 or 4 or more, and then DEG-DA5 20% combination cream (Example 3) and liquid paraffin 20% combination cream (Comparative Example 1). Vaseline showed fewer results when compared with 8 subjects and 15 subjects who had no application on the SLS sticking visual evaluation score of 3 or 4, but compared with DEG-DA5 and DEG-DA5 combination cream. There were many people.
As a result of Wilcoxon signed rank sum test, petrolatum was applied at DEG-DA5 application site (Example 1), DEG-DA5 20% combination cream (Example 3) application site, and DEG-DA5 5% cream (Example 5) application site. The score was significantly lower than the application site (p <0.05). Moreover, the stimulation score of DEG-DA5 20% combination cream (Example 3) was significantly suppressed compared to the squalane 20% combination cream (Comparative Example 2) (p <0.05).
The 7th day determination was performed to confirm the presence or absence of allergic symptoms. As a result, only one test subject showed a score of 1 or more, which was the SLS application site in the non-application area, and there was no effect of the pretreatment agent.
８．機器測定による経表皮水分蒸散量
表１３、図５、図６に各被験物質の経表皮水分蒸散量値の平均値を示す。貼付２４ｈ後では、SLS貼付部位でその刺激性によるＴＥＷＬ値抑制傾向が認められた箇所はＤＥＧ−ＤＡ５（実施例１）、ＤＥＧ−ＤＡ５ ２０％配合クリーム（実施例３）、ＤＥＧ−ＤＡ５ １０％配合クリーム（実施例４）であった。ＤＥＧ−ＤＡ５ ２０％クリーム（実施例３）、ＤＥＧ−ＤＡ５ １０％クリーム（実施例４）は無塗布部位に対して、またＤＥＧ−ＤＡ５ ２０％クリーム（実施例３）はワセリン塗布部位に対しても有為に刺激抑制効果が認められた(p<0.05)。貼付４８ｈ後では、すべての前処理剤において無塗部位と比較するとSLS貼付によるＴＥＷＬ値上昇が有為に抑制されていた（p<0.05）。特にＤＥＧ−ＤＡ５（実施例１）、ＤＥＧ−ＤＡ５ ２０％配合クリーム（実施例３）ではワセリン塗布部位と比較しても有為に抑制された（ｐ<0.05）。8). Transepidermal moisture transpiration by instrument measurement Tables 13, 5 and 6 show the average transepidermal moisture transpiration values of each test substance. After 24 hours after application, the SLS application site where the tendency to suppress TEWL value due to irritation was observed was DEG-DA5 (Example 1), DEG-DA5 20% combination cream (Example 3), DEG-DA5 10%. It was a combination cream (Example 4). DEG-DA5 20% cream (Example 3), DEG-DA5 10% cream (Example 4) for the non-application site, and DEG-DA5 20% cream (Example 3) for the petrolatum application site. Also had a significant stimulus-suppressing effect (p <0.05). 48 hours after application, the increase in TEWL due to application of SLS was significantly suppressed in all pretreatment agents compared to the uncoated area (p <0.05). In particular, DEG-DA5 (Example 1) and DEG-DA5 20% cream (Example 3) were significantly suppressed (p <0.05) even when compared with the petrolatum application site.
１３．まとめ
本試験では、ＤＥＧ−ＤＡ５およびＤＥＧ−ＤＡ５を配合したクリームの刺激成分浸透抑制効果をアトピー性皮膚炎患者の方、皮脂欠乏症の方２０名を対象にして検証した。その結果、ＤＥＧ−ＤＡ５およびＤＥＧ−ＤＡ５配合クリームが濃度依存的にＳＬＳの刺激を抑制する傾向が認められ、ヒトに用いる際に効果を発揮するおおよその濃度が示唆された。
また、ＤＥＧ−ＤＡ５およびＤＥＧ−ＤＡ５配合クリームのアトピー性皮膚炎疾患者、皮脂欠乏症疾患者に対する２４時間クローズドパッチテストによる安全性確認ができた。
以上の結果より、ＤＥＧ−ＤＡ５を配合した化粧料は、バリア機能が低下したアトピー性皮膚炎疾患者、皮脂欠乏症者の使用に適している。13. Summary In this test, the stimulant component penetration inhibitory effect of the cream containing DEG-DA5 and DEG-DA5 was examined for 20 patients with atopic dermatitis and 20 with sebum deficiency. As a result, the tendency for DEG-DA5 and DEG-DA5 combination cream to suppress the stimulation of SLS in a concentration-dependent manner was recognized, suggesting an approximate concentration that exerts an effect when used in humans.
In addition, safety of DEG-DA5 and DEG-DA5 combination cream was confirmed by a 24-hour closed patch test for patients with atopic dermatitis and those with sebum deficiency.
From the above results, the cosmetics containing DEG-DA5 are suitable for use by people with atopic dermatitis and those with sebum deficiency with reduced barrier function.
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