TW201620494A - Composition, cosmetic material - Google Patents

Composition, cosmetic material Download PDF

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TW201620494A
TW201620494A TW104109858A TW104109858A TW201620494A TW 201620494 A TW201620494 A TW 201620494A TW 104109858 A TW104109858 A TW 104109858A TW 104109858 A TW104109858 A TW 104109858A TW 201620494 A TW201620494 A TW 201620494A
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acid
composition
cosmetic
neuropterin
solution
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TW104109858A
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TWI668014B (en
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宮地樹
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高絲股份有限公司
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0208Tissues; Wipes; Patches
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/68Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations

Abstract

A composition including ceramide and labdenoic acid, and a cosmetic material including the above composition is provided.

Description

組成物、化妝料 Composition, cosmetics

本發明是有關於一種組成物、化妝料。 The present invention relates to a composition and a cosmetic.

皮膚表面的角質層主要包含角質細胞與角質細胞間脂質。角質細胞間脂質擔負如下作用:將角質細胞彼此維繫在一起,構築脂質障壁(barrier),防止異物自外部侵入,並且將水分維持於皮膚內部。角質細胞間脂質是以神經鞘胺醇(sphingosine)與脂肪酸進行醯胺鍵結而成的化合物群(神經醯胺(ceramide))作為主成分。 The stratum corneum of the skin surface mainly contains keratinocytes and keratinocyte lipids. The keratinocyte intercellular lipid acts to maintain keratinocytes to each other, to construct a lipid barrier, to prevent foreign matter from invading from the outside, and to maintain moisture inside the skin. The keratinocyte intercellular lipid is a group of compounds (ceramide) in which sphingosine is bonded to a fatty acid by a sphingosine (ceramide) as a main component.

若能夠將神經醯胺自體外供給至皮膚表面,則可改善障壁功能等。因此,神經醯胺作為塗佈於皮膚表面的化妝料或皮膚外用劑的成分而受到關注。 If the neuropterin can be supplied to the skin surface from the outside, the barrier function and the like can be improved. Therefore, neuroterpene is attracting attention as a component of a cosmetic or skin external preparation applied to the skin surface.

然而,神經醯胺由於結晶性高,故而有在化妝料等組成物中的穩定性低的課題。 However, since neuroamide has high crystallinity, there is a problem that stability in a composition such as a cosmetic is low.

為了解決該課題而嘗試的組成物已知有神經醯胺類中含有特定的聚甘油脂肪酸酯或甘油單脂肪酸酯的至少一種的含神經醯胺類的組成物(參照專利文獻1、專利文獻2)。根據該組成物,可將神經醯胺類的結晶化.析出抑制為規定程度。 A composition containing at least one of a specific polyglycerin fatty acid ester or a glycerin mono-fatty acid ester in a neuropterin is known as a composition which has been tried to solve the problem (see Patent Document 1 and Patent). Literature 2). According to the composition, the ceramides can be crystallized. The precipitation inhibition is a predetermined level.

[現有技術文獻] [Prior Art Literature] [專利文獻] [Patent Literature]

專利文獻1:日本專利特開2011-073992號公報 Patent Document 1: Japanese Patent Laid-Open No. 2011-073992

專利文獻2:日本專利特開2013-053146號公報 Patent Document 2: Japanese Patent Laid-Open Publication No. 2013-053146

然而,所述先前的組成物尚有抑制神經醯胺類的結晶化.析出的餘地。 However, the previous composition still inhibits the crystallization of neuralamines. The room for precipitation.

因此,本發明的目的在於提供一種可抑制組成物中神經醯胺類結晶化而析出,從而可提高神經醯胺類在組成物中的穩定性的組成物,及可抑制化妝料中神經醯胺類結晶化而析出,從而可提高神經醯胺類在化妝料中的穩定性的化妝料。 Accordingly, an object of the present invention is to provide a composition which can suppress the crystallization of a neuropterin in a composition and precipitate, thereby improving the stability of the neuropterin in the composition, and suppressing the nerve amide in the cosmetic. A cosmetic which crystallizes and precipitates, thereby improving the stability of the neuropterin in the cosmetic.

本發明的主旨如下所述。 The gist of the present invention is as follows.

本發明的組成物的特徵在於:包含神經醯胺類與勞丹酸(labdenoic acid)類。此處,本發明的組成物中,所述勞丹酸類相對於所述神經醯胺類的比例較佳為0.01~100,進而較佳為0.1~50。 The composition of the present invention is characterized by comprising a neurosteroid and a labdenoic acid. Here, in the composition of the present invention, the ratio of the labousanic acid to the neurosteroid is preferably from 0.01 to 100, more preferably from 0.1 to 50.

本發明的化妝料的特徵在於:包含所述本發明的組成物。 The cosmetic of the present invention is characterized by comprising the composition of the present invention.

此外,關於本發明的組成物及本發明的化妝料中所含的成分的「比例」是指質量比例。 Further, the "ratio" of the components of the present invention and the components contained in the cosmetic of the present invention means the mass ratio.

根據本發明的組成物,可抑制組成物中神經醯胺類結晶化而析出,從而可提高神經醯胺類在組成物中的穩定性。根據本發明的化妝料,可抑制化妝料中神經醯胺類結晶化而析出,從而可提高神經醯胺類在化妝料中的穩定性。 According to the composition of the present invention, it is possible to suppress the crystallization of the neuropterin in the composition and precipitate it, thereby improving the stability of the neuropterin in the composition. According to the cosmetic of the present invention, it is possible to suppress the precipitation of the neuropterin in the cosmetic material, thereby improving the stability of the neuropterin in the cosmetic.

圖1是表示使用直立式顯微鏡在倍率20倍、曝光時間1/300秒的條件下在偏光下對依據本發明的組成物及成為本發明的比較例的組成物進行顯微鏡觀察所得的結果的照片。(a)是包含神經醯胺類與勞丹酸類的依據本發明的組成物(實施例A7)的情況下的照片,(b)是包含神經醯胺類與荷荷芭油的成為本發明的比較例的組成物(比較例A3)的情況下的照片。 1 is a photograph showing the results of microscopic observation of a composition according to the present invention and a composition which is a comparative example of the present invention under polarized light at a magnification of 20 times and an exposure time of 1/300 second using an upright microscope. . (a) is a photograph of a composition containing the neuropterin and labousic acid according to the present invention (Example A7), and (b) is a composition comprising a neural amine and jojoba oil which is the present invention. Photograph of the composition of Comparative Example (Comparative Example A3).

以下,對本發明的組成物及本發明的化妝料的實施形態進行詳細地例示說明。 Hereinafter, embodiments of the composition of the present invention and the cosmetic of the present invention will be described in detail.

(組成物) (composition)

本發明的一例的組成物(以下,亦稱為「一例的組成物」)必須包含神經醯胺類與勞丹酸類。 The composition of one example of the present invention (hereinafter also referred to as "an example of a composition") must contain a neurosteroid and a labothelic acid.

本發明發現在包含神經醯胺類與勞丹酸類的組成物中,勞丹酸類具有緩和神經醯胺類的結晶性的效果。根據本發明的組成物,可抑制組成物中神經醯胺類結晶化而析出,從而可提高神經醯胺類在組成物中的穩定性。雖已知勞丹酸類具有保濕效 果、美白效果等,但是具有抑制神經醯胺類的結晶化.析出的效果的情況在任一文獻中均既無記載亦無提示。 The present inventors have found that a labranate has an effect of alleviating the crystallinity of a neurosteroid in a composition containing a neurosteroid and a labothenic acid. According to the composition of the present invention, it is possible to suppress the crystallization of the neuropterin in the composition and precipitate it, thereby improving the stability of the neuropterin in the composition. Although it is known that Laudans have a moisturizing effect Fruit, whitening effect, etc., but with inhibition of ceramide crystallization. The case of the effect of precipitation is neither documented nor suggested in any of the documents.

另外,根據本發明的組成物,如上所述,神經醯胺類在組成物中的穩定性提高,因此可將神經醯胺類均勻地塗佈於皮膚上。因此,可提高皮膚表面的角質層的障壁功能、進而防止異物侵入的效果及保濕效果。 Further, according to the composition of the present invention, as described above, the stability of the neuroketamine in the composition is improved, so that the nervous amine can be uniformly applied to the skin. Therefore, the barrier function of the stratum corneum on the skin surface, the effect of preventing foreign matter from entering, and the moisturizing effect can be improved.

-神經醯胺類- -Neuroamines -

本發明中的神經醯胺類是指具有神經鞘胺醇類(sphingoid)與脂肪酸進行醯胺鍵結而成的結構作為基本結構的化合物(以下,亦稱為「基本神經醯胺」)、所述基本神經醯胺的衍生物(以下,亦稱為「神經醯胺衍生物」)、模仿所述基本神經醯胺及其衍生物而合成的類緣物(以下,亦稱為「神經醯胺類似物」)、神經鞘胺醇類。 The ceramide in the present invention is a compound having a structure in which a sphingoid and a fatty acid are bonded to a fatty acid as a basic structure (hereinafter, also referred to as "basic neuropterin"). a derivative of basic neuropterin (hereinafter also referred to as "neuroguanamine derivative"), a rim similar to the basic neuropterin and its derivative (hereinafter, also referred to as "neuroguanamine" Analogs"), sphingosines.

本發明中的神經醯胺類可源自合成物、天然物(例如植物萃取物)等。 The neuropteramines in the present invention may be derived from synthetics, natural products (e.g., plant extracts), and the like.

--基本神經醯胺-- --Basic nervous amine --

基本神經醯胺所具有的基本結構可列舉下述式(S1)所示的結構。 The basic structure of the basic neuropterin includes a structure represented by the following formula (S1).

此外,所述式(S1)所示的基本神經醯胺中,神經醯胺1~神經醯胺10尤其為人類的角質層中所含的神經醯胺(皮膚神經醯胺)。 Further, among the basic neuropterin represented by the formula (S1), the neurosteroid 1 to the neurosteroid 10 is particularly a neuropterin (skin ceramide) contained in the stratum corneum of a human.

另外,實際上,源自人類或其以外的動物等的神經醯胺中,關於所述式(S1)中所示的神經鞘胺醇類及脂肪酸的烷基鏈長,存在各種變形例。所述基本神經醯胺中亦包含具有除烷基鏈長以外與所述式(S1)中所示的化合物相同的骨架的化合物。 In addition, in the nervous guanamine derived from humans or other animals, there are various modifications regarding the alkyl sphingoids and the alkyl chain length of the fatty acid shown in the above formula (S1). The basic neuropterin also contains a compound having the same skeleton as the compound represented by the formula (S1) except for the alkyl chain length.

進而,所述基本神經醯胺可使用天然型(D(-)體)的光學 活性體,亦可使用非天然型(L(+)體)的光學活性體,進而亦可使用天然型與非天然型的混合物。關於所述基本神經醯胺的結構中的多個不對稱碳的相對立體配置可為天然型的立體配置,亦可為其以外的非天然型的立體配置,另外亦可為由該等的混合物所得的立體配置。 Further, the basic neuropterin can be optical using a natural type (D(-) body) As the active material, an optically active substance of a non-natural type (L(+) body) may be used, and a mixture of a natural type and an unnatural type may also be used. The relative steric arrangement of the plurality of asymmetric carbons in the structure of the basic neural guanamine may be a natural stereo configuration, or a non-natural stereo configuration other than the other, or may be a mixture of the same The resulting stereo configuration.

神經醯胺類中所含的神經鞘胺醇類部分可列舉天然型神經鞘胺醇及其類緣物。作為天然型神經鞘胺醇,具體而言,可列舉:神經鞘胺醇、二氫神經鞘胺醇、植物鞘胺醇(phytosphingosine)、6-羥基神經鞘胺醇(以上,以所述式(S1)表示)、神經鞘胺二烯醇(sphingadienine)、脫氫神經鞘胺醇、脫氫植物鞘胺醇、以及該等的N-烷基化體(例如N-甲基化體)及乙醯化體等衍生物等。 The sphingoid alcohol moiety contained in the neuropterin includes natural sphingosine and its rim. Specific examples of the natural sphingosine include sphingosine, dihydrosphingosine, phytosphingosine, and 6-hydroxysphingosine (above, S1), sphingadienine, dehydrosphingosine, dehydrogenated sphingosine, and N-alkylated compounds (eg, N-methylated) and B Derivatives such as sputum and the like.

神經醯胺類中所含的脂肪酸部分可列舉:飽和脂肪酸、α-羥基脂肪酸、ω-羥基脂肪酸、及該等的衍生物等。 Examples of the fatty acid moiety contained in the neuropterin include a saturated fatty acid, an α-hydroxy fatty acid, an ω-hydroxy fatty acid, and the like.

神經醯胺類中所含的神經鞘胺醇類部分及脂肪酸部分可源自合成物、天然物(例如植物萃取物)等。 The sphingosine moiety and the fatty acid moiety contained in the neuropterin may be derived from a composition, a natural product (for example, a plant extract), or the like.

--神經醯胺衍生物-- --Neuroamine derivatives --

神經醯胺衍生物可列舉藉由糖類在分子內經修飾的神經醯胺化合物(以下,亦稱為「糖神經醯胺」)等。糖神經醯胺中所使用的糖類例如可列舉:葡萄糖(glucose)、半乳糖(galactose)等單糖類;乳糖(lactose)、麥芽糖(maltose)等二糖類;該等單糖類或二糖類藉由葡糖苷(glucoside)鍵結而高分子化的寡糖類或多 糖類等。另外,其他神經醯胺衍生物亦可列舉所述糖神經醯胺中藉由糖類的糖單元中所含的羥基經其他官能基取代的糖類類緣物在分子內經修飾的神經醯胺化合物(以下,亦稱為「糖神經醯胺類緣物」)。糖神經醯胺類緣物中所使用的糖類類緣物例如可列舉:葡萄糖胺(glucosamine)、葡萄糖醛酸(glucuronic acid)、N-乙醯基葡萄糖胺等。 The neural guanamine derivative may, for example, be a neuroindolamine compound (hereinafter, also referred to as "glycosideamine") modified by a saccharide in a molecule. Examples of the saccharide to be used in the glycosylamine include monosaccharides such as glucose and galactose; disaccharides such as lactose and maltose; and monosaccharides or disaccharides by Portuguese. Or oligosaccharide or oligosaccharide Sugar and so on. Further, other neuropterin derivatives may also be exemplified by a neurosteroid compound in which a saccharide-like substance substituted by a hydroxyl group contained in a saccharide unit of a saccharide is modified in the molecule by a saccharide-like saccharide (hereinafter, Also known as "sugar-ceramides"). Examples of the saccharide-like material to be used in the glycosylamine-based rims include glucosamine, glucuronic acid, and N-acetyl glucosamine.

就組成物中的分散穩定性的觀點而言,糖神經醯胺及糖神經醯胺類緣物中的糖單元的個數較佳為1~5,更佳為1或2(在糖神經醯胺的情況下,糖類分別為葡萄糖或乳糖),尤佳為1。 The number of saccharide units in the glycosylamine and the glycosylamine steroid is preferably from 1 to 5, more preferably 1 or 2, from the viewpoint of dispersion stability in the composition (in the glycoside) In the case of an amine, the saccharide is glucose or lactose, respectively, and particularly preferably 1.

糖神經醯胺及糖神經醯胺類緣物可藉由化學合成而獲取,亦可藉由購入市售品而獲取。 Glycosylamines and glycosylamines can be obtained by chemical synthesis or by the purchase of commercially available products.

糖神經醯胺的市售品例如可列舉岡安商店公司製造的(商品名)「植物鞘胺醇液FRl」。 For the commercial product of the glycosaminoglycan, for example, the product name "plant sphingosine alcohol liquid FR1" manufactured by Gunan Store Co., Ltd. is mentioned.

--神經醯胺類似物-- --Neuroamine analogues --

神經醯胺類似物例如可列舉下述式(S2)所示的神經醯胺化合物。 The neural guanamine compound is exemplified by the following formula (S2).

--神經鞘胺醇類-- --Sphingosine --

進而,本發明中的神經醯胺類中亦包含神經鞘胺醇類。神經鞘胺醇類可列舉所述的神經醯胺類中所含的神經鞘胺醇類部分所使用者。 Further, the sphingosines of the present invention also include sphingosine. Examples of the sphingosine include those of the sphingosine moiety contained in the above-mentioned neuropterin.

可較佳地用於本發明的植物鞘胺醇的具體例例如可列舉:贏創高施米特(Evonik Goldschmidt GmbH)公司製造的(商品名)「Phytosphingosine」。 Specific examples of the phytosphingosine which can be preferably used in the present invention include, for example, "Phytosphingosine" (trade name) manufactured by Evonik Goldschmidt GmbH.

作為所述神經醯胺類所例示者可單獨使用一種,亦可組合使用兩種以上。 As the exemplified by the ceramides, one type may be used alone or two or more types may be used in combination.

就充分地獲得所述本發明的效果的觀點而言,本發明中的神經醯胺類較佳為基本神經醯胺,進而較佳為皮膚神經醯胺,尤佳為神經醯胺2。 From the viewpoint of sufficiently obtaining the effects of the present invention, the neuropterin in the present invention is preferably a basic neuropterin, and more preferably a skin ceramide, and more preferably a neuropterin 2.

-勞丹酸類- - Laudans -

本發明中的勞丹酸類是指下述式(S3)所示的化合物。 The labudaic acid in the present invention means a compound represented by the following formula (S3).

[式中,R1表示-CH2OH或COOR6,此處,R6表示氫、碳數為1~3的低級烷基或可與COO-形成鹽的陽離子(cation),R2~R5 分別獨立地表示氫原子或甲基,…A…表示=C(CH3)-、-C(CH3)=、-C(=CH2)-、-CH(CH3)-或-C(OH)(CH3)-]。 Wherein R 1 represents -CH 2 OH or COOR 6 , wherein R 6 represents hydrogen, a lower alkyl group having 1 to 3 carbon atoms or a cation capable of forming a salt with COO-, R 2 to R 5 independently represents a hydrogen atom or a methyl group, and ... A... represents =C(CH 3 )-, -C(CH 3 )=, -C(=CH 2 )-, -CH(CH 3 )- or -C (OH)(CH 3 )-].

本發明中的勞丹酸類可源自合成物、天然物(例如植物萃取物)等。 The labothelic acid in the present invention may be derived from a composition, a natural product (for example, a plant extract), or the like.

所述式(S3)所示的化合物包含下述式(S4)所示的化合物, The compound represented by the formula (S3) contains a compound represented by the following formula (S4).

[式中,基於3條虛線的鍵表示2個單鍵及1個雙鍵],該化合物包含下述式(S5)~式(S7)所示的勞丹-8-烯-15-酸((S5))、勞丹-7-烯-15-酸((S6))、勞丹-8(17)-烯-15-酸((S7))。 [In the formula, the three dash-based bonds represent two single bonds and one double bond], and the compound contains the labdan-8-ene-15-acid represented by the following formula (S5) to (S7) ( (S5)), labdan-7-ene-15-acid ((S6)), labdan-8(17)-ene-15-acid ((S7)).

此外,所述式(S5)~式(S7)的化合物可分別藉由加熱或 酸觸媒存在下的加熱而異構化,可使(S5)與(S6)與(S7)的比變化為例如約1:1:1、8:2:0或7:3:0等。 Further, the compounds of the formula (S5) to (S7) may be respectively heated or The isomerization is carried out by heating in the presence of an acid catalyst, and the ratio of (S5) to (S6) to (S7) can be changed to, for example, about 1:1:1, 8:2:0 or 7:3:0 or the like.

作為所述勞丹酸類所例示者可單獨使用一種,亦可組合使用兩種以上。 As the exemplified as the labyrin acid, one type may be used alone or two or more types may be used in combination.

本發明中所使用的勞丹酸類在分子中所具有的羧基可為游離的羧酸,亦可為羧酸鹽、例如鈉鹽、鉀鹽等鹼金屬鹽;鈣鹽、鎂鹽等鹼土金屬鹽;銨鹽;單甲基銨鹽等一級胺鹽、二甲基銨鹽、二環己基銨鹽等二級胺鹽、三甲基銨鹽等三級胺鹽等胺鹽。 The carboxyl group of the labothelic acid used in the present invention may be a free carboxylic acid, or may be a carboxylate, an alkali metal salt such as a sodium salt or a potassium salt; an alkaline earth metal salt such as a calcium salt or a magnesium salt. An ammonium salt; a primary amine salt such as a monomethylammonium salt; a secondary amine salt such as a dimethylammonium salt or a dicyclohexylammonium salt; or an amine salt such as a tertiary amine salt such as a trimethylammonium salt.

若將羧基設為游離的羧酸,則可提高勞丹酸類的油溶性,另外,若將羧基設為羧酸鹽,則可提高勞丹酸類的水溶性。因此,本發明中,可將水溶性的勞丹酸類與油溶性的勞丹酸類視需要分開使用。 When the carboxyl group is a free carboxylic acid, the oil solubility of the lauric acid can be improved, and when the carboxyl group is a carboxylate, the water solubility of the lauric acid can be improved. Therefore, in the present invention, water-soluble labrinic acid and oil-soluble labousic acid can be used separately as needed.

自游離的羧酸向羧酸鹽的轉化例如可藉由與鹼金屬氫氧化物、鹼土金屬氫氧化物、胺等的反應而容易地進行,反之,自羧酸鹽向游離的羧酸的轉化例如可藉由與鹽酸、硫酸等的反應而容易地進行。 The conversion of the free carboxylic acid to the carboxylate can be easily carried out, for example, by reaction with an alkali metal hydroxide, an alkaline earth metal hydroxide, an amine or the like, and vice versa, from a carboxylate to a free carboxylic acid. For example, it can be easily carried out by reaction with hydrochloric acid, sulfuric acid or the like.

在藉由化學合成獲得勞丹酸類的情況下,合成法例如可使用藉由勞丹醇酸的脫水反應而製成勞丹酸類的方法(J.Chem.Soc.,1956,4262-4271)。另外,另一合成法亦可使用如下方法:首先,將淚柏醇(manool)或香紫蘇醇(sclareol)藉由使用醇作為溶劑,使用釩酸類或鉬酸類作為觸媒,在硼酸存在下進行的烯丙基重排反應而製成烯丙醇,其後,將該烯丙醇藉由使用 釕-膦錯合物作為觸媒的氧化反應而製成醛,進而,將該醛藉由在亞氯酸鈉等氧化劑及醯胺硫酸存在下進行的氧化反應而製成羧酸,最後,將羧酸藉由使用酸觸媒的脫水反應而製成勞丹酸類。 In the case where the labothelic acid is obtained by chemical synthesis, the synthesis method can be, for example, a method of producing a labranic acid by a dehydration reaction of Laudanic acid (J. Chem. Soc., 1956, 4262-4271). In addition, another synthesis method may also use the following method: First, using manool or sclareol by using an alcohol as a solvent, using vanadium or molybdic acid as a catalyst, in the presence of boric acid Allyl rearrangement reaction to form allyl alcohol, after which the allyl alcohol is used The hydrazine-phosphine complex is used as an oxidation reaction of a catalyst to form an aldehyde, and further, the aldehyde is formed into a carboxylic acid by an oxidation reaction in the presence of an oxidizing agent such as sodium chlorite or guanamine sulfuric acid, and finally, The carboxylic acid is made into a labdanic acid by a dehydration reaction using an acid catalyst.

在藉由自植物的萃取而獲得勞丹酸類的情況下,所使用的植物只要為包含勞丹酸類或其鹽的植物則並無特別限定,較佳為半日花科(Cistaceae)的植物,尤其更佳為半日花科的Cistus ladaniferus L.、Cistus creticus L.、Cistus monoperiensis L.、Cistus salvifolius。該等植物可單獨使用一種,亦可組合使用兩種以上。 In the case of obtaining a labothelic acid by extraction from a plant, the plant to be used is not particularly limited as long as it is a plant containing a labophyllin or a salt thereof, and is preferably a plant of the family Cistaceae, especially More preferably, Cistus ladaniferus L., Cistus creticus L., Cistus monoperiensis L., Cistus salvifolius . These plants may be used alone or in combination of two or more.

萃取中所使用的植物的部位並無特別限定,可列舉葉、枝、幹、及樹皮等。另外,萃取可在採集植物後立即進行,亦可在所採集的植物的乾燥後進行,亦可在經乾燥的植物的處理(例如,裁剪或粉末化)後進行。萃取中所使用的溶劑理想為水、低級醇、石油醚、烴、或該等的組合。此處,低級醇是指碳數為1~4的醇,其中,較佳為甲醇、乙醇。 The part of the plant used for the extraction is not particularly limited, and examples thereof include leaves, branches, stems, and bark. Alternatively, the extraction may be carried out immediately after the collection of the plants, or after drying of the collected plants, or after treatment (for example, cutting or powdering) of the dried plants. The solvent used in the extraction is desirably water, a lower alcohol, a petroleum ether, a hydrocarbon, or a combination thereof. Here, the lower alcohol refers to an alcohol having 1 to 4 carbon atoms, and among them, methanol or ethanol is preferred.

此處,勞丹酸類相對於神經醯胺類的比例較佳為0.01以上。若將所述比例設為0.01以上,則可充分確保提高神經醯胺類在組成物中的穩定性的所述效果。另外,所述比例較佳為100以下。若將所述比例設為100以下,則可獲得確保將水分保持於角質層中的神經醯胺類的效果、以及提高神經醯胺類在組成物中的穩定性的所述效果。 Here, the ratio of the labdanic acid to the neurosteroid is preferably 0.01 or more. When the ratio is made 0.01 or more, the effect of improving the stability of the neuropterin in the composition can be sufficiently ensured. Further, the ratio is preferably 100 or less. When the ratio is 100 or less, the effect of ensuring the retention of moisture in the stratum corneum and the effect of improving the stability of the neuropterin in the composition can be obtained.

關於勞丹酸類相對於神經醯胺類的比例,根據與所述下限的意義相同的意義,較佳為0.1以上,進而較佳為0.25以上, 另外,根據與所述上限的意義相同的意義,較佳為50以下,進而較佳為20以下。 The ratio of the labdanic acid to the neurosteroid is preferably 0.1 or more, and more preferably 0.25 or more, in the same meaning as the lower limit. Further, it is preferably 50 or less, and more preferably 20 or less, in the same meaning as the meaning of the upper limit.

一例的組成物可為僅包含神經醯胺類與勞丹酸類的組成物。該情況下,可將神經醯胺類與勞丹酸類在無溶劑下混合。 An example of the composition may be a composition containing only a nervous amine and a labothenic acid. In this case, the neural amines and the labousuric acid can be mixed without a solvent.

一例的組成物亦可含有除神經醯胺類及勞丹酸類以外的成分。除神經醯胺類及勞丹酸類以外的成分可列舉:油劑、醇類、水、界面活性劑、保濕劑、凝膠化劑(水性凝膠化劑及油性凝膠化劑)及增黏劑、粉體、紫外線吸收劑、防腐劑及抗菌劑、抗氧化劑、美容成分(美白劑、細胞活化劑、抗炎症劑、血液循環促進劑、皮膚收斂劑、抗脂漏劑等)、維生素類、胺基酸類、核酸、激素等。該等可單獨使用一種,亦可組合使用兩種以上。 An example of the composition may contain components other than the nervous amines and the labousin. In addition to the components of the nervous amines and the labousuric acid, oils, alcohols, water, surfactants, humectants, gelling agents (aqueous gelling agents and oily gelling agents) and viscosity-increasing agents may be mentioned. Agent, powder, UV absorber, preservative and antibacterial agent, antioxidant, beauty ingredients (whitening agent, cell activator, anti-inflammatory agent, blood circulation promoter, skin astringent, anti-lipid leakage agent, etc.), vitamins , amino acids, nucleic acids, hormones, and the like. These may be used alone or in combination of two or more.

(化妝料) (cosmetic)

本發明的一例的化妝料(以下,亦稱為「一例的化妝料」)必須包含本發明的一例的組成物。 The cosmetic of one example of the present invention (hereinafter also referred to as "an example of a cosmetic") must contain a composition of an example of the present invention.

根據本發明的化妝料,可獲得所述的本發明的組成物的效果、即可獲得提高神經醯胺類在化妝料中的穩定性的效果、提高皮膚表面的角質層的障壁功能、進而防止異物侵入的效果及保濕效果的效果。 According to the cosmetic of the present invention, the effect of the composition of the present invention can be obtained, the effect of improving the stability of the neuropterin in the cosmetic, the barrier function of the stratum corneum on the skin surface, and the prevention can be prevented. The effect of foreign matter intrusion and the effect of moisturizing effect.

神經醯胺類相對於一例的化妝料的比例可設為0.0001質量%以上,較佳為0.001質量%以上,進而較佳為0.005質量%以上。另外,所述比例可設為10質量%以下,較佳為5質量%以下,進而較佳為1質量%以下。 The ratio of the neuropterin to the cosmetic of one example can be 0.0001% by mass or more, preferably 0.001% by mass or more, and more preferably 0.005% by mass or more. Further, the ratio may be 10% by mass or less, preferably 5% by mass or less, and more preferably 1% by mass or less.

另外,勞丹酸類相對於一例的化妝料的比例可設為0.0005質量%以上,較佳為0.001質量%以上,進而較佳為0.01質量%以上。另外,所述比例可設為20質量%以下,較佳為10質量%以下,進而較佳為1質量%以下。 In addition, the ratio of the labdanic acid to the cosmetic of one example may be 0.0005% by mass or more, preferably 0.001% by mass or more, and more preferably 0.01% by mass or more. Further, the ratio may be 20% by mass or less, preferably 10% by mass or less, and more preferably 1% by mass or less.

一例的化妝料中,就提高本發明的化妝料的效果的觀點而言,作為除神經醯胺類及勞丹酸類以外的成分,較佳為使用適當選擇的界面活性劑,進而較佳為使用陰離子性及/或非離子性的界面活性劑,尤佳為使用水溶性非離子性的界面活性劑。 In the case of the cosmetic of the present invention, it is preferable to use a suitably selected surfactant as a component other than the ceramide and the labothenic acid, and it is preferable to use it. Anionic and/or nonionic surfactants are particularly preferred for use with water-soluble, nonionic surfactants.

作為本發明的化妝料中的神經醯胺類,如上所述,就提高障壁功能等的觀點而言,較佳為天然型的光學活性體,進而較佳為神經醯胺1、神經醯胺2、神經醯胺3、神經醯胺4、神經醯胺5、神經醯胺6、神經鞘胺醇、植物鞘胺醇、糖神經醯胺,若亦一併考慮通用性,則尤佳為神經醯胺2、神經醯胺3、神經醯胺6。 As described above, the neurosteroids in the cosmetic of the present invention are preferably a natural optically active substance, and more preferably a neuropterin or a neuropterin 2, from the viewpoint of improving the barrier function and the like. , neuropterin 3, neuropterin 4, neuropterin 5, neuropterin 6, sphingosine, phytosphingosine, glycosylamine, if also considered versatility, it is especially good for neural crest Amine 2, neural guanamine 3, neural guanamine 6.

就抑制神經醯胺類的結晶化.析出的觀點或提高障壁功能等的觀點而言,本發明的化妝料中的勞丹酸類較佳為所述的勞丹-8-烯-15-酸(式(S5))、勞丹-7-烯-15-酸(式(S6))、勞丹-8(17)-烯-15-酸(式(S7))。 Inhibition of the crystallization of neuralamines. From the viewpoint of precipitation or the function of improving the barrier function, the labousanic acid in the cosmetic of the present invention is preferably the labdan-8-ene-15-acid (formula (S5)) or labdan-7. -ene-15-acid (formula (S6)), labdan-8(17)-ene-15-acid (formula (S7)).

一例的化妝料例如可以液狀、乳液狀、乳霜(cream)狀、固體狀、凝膠(gel)狀、膏(paste)狀等各種形態製備。另外,一例的化妝料可以油性系、油中水型乳化系、水中油型乳化系等各種劑形製備。一例的化妝料具體而言可為化妝水、乳液、乳霜、美容液、化妝油、潤唇膏(lip cream)、護手霜(hand cream)、 洗面乳、去污(cleansing)料等護膚(skincare)化妝料;粉底(foundation)、隔離霜(makeup base)、腮紅、眼影(eye shadow)、睫毛膏(mascara)、眼線(eyeliner)、眉毛(eyebrow)、定妝劑(over coat agent)、口紅、唇彩(lip gloss)等彩妝(makeup)化妝料;養髮露(hair tonic)、髮乳(hair cream)、洗髮精(shampoo)、潤絲精(rinse)、護髮素(conditioner)、整發料等頭皮或毛髪用的化妝料;按摩(massage)化妝料等各種化妝料。 An example of a cosmetic can be prepared in various forms such as a liquid, an emulsion, a cream, a solid, a gel, or a paste. Further, an example of the cosmetic preparation can be prepared in various forms such as an oily system, an oil-in-water emulsion system, or an oil-in-water emulsion system. An example of a cosmetic may be a lotion, an emulsion, a cream, a beauty lotion, a makeup oil, a lip cream, a hand cream, or the like. Skincare cosmetics such as facial cleansers, cleansing materials; foundation, makeup base, blush, eye shadow, mascara, eyeliner, eyebrows (eyebrow), over coat agent, lipstick, lip gloss, etc. Makeup makeup; hair tonic, hair cream, shampoo, moisturizing A cosmetic material for scalp or hair styling such as rinse, conditioner, and hair styling; and various cosmetic materials such as massage cosmetics.

此外,本發明的化妝料亦包含準藥品(medicated cosmetics)。另外,本發明的組成物亦可包含於所述化妝料以外者、例如皮膚外用劑。 Further, the cosmetic of the present invention also contains medicated cosmetics. Further, the composition of the present invention may be contained in addition to the cosmetic, for example, an external preparation for skin.

本發明的組成物例如可藉由如下方式而製造:將神經醯胺類與勞丹酸類混合,將該混合物在高於神經醯胺類的熔點的溫度(例如70℃~140℃)下進行加熱,其後緩慢地(例如以2℃/min~30℃/min)冷卻。 The composition of the present invention can be produced, for example, by mixing a neural amine with a labousuric acid, and heating the mixture at a temperature higher than the melting point of the neuropterin (for example, 70 to 140 ° C). Thereafter, it is slowly cooled (for example, at 2 ° C / min to 30 ° C / min).

如本申請案說明書的記載所示,本發明可提供一種以勞丹酸類作為有效成分的神經醯胺類的結晶化.析出抑制劑、及使用勞丹酸類的神經醯胺類的結晶化.析出抑制方法。 As shown in the description of the specification of the present application, the present invention can provide a crystallization of a nervous steroid containing labyronic acid as an active ingredient. Crystallization of precipitation inhibitors and neuralamines using labranate. Precipitation inhibition method.

[實施例] [Examples]

以下,藉由實施例更詳細地說明本發明,但本發明並不受下述實施例的任何限定。 Hereinafter, the present invention will be described in more detail by way of examples, but the invention should not be construed as limited.

<試驗P>勞丹酸的製造 <Test P>Manufacture of Laudanic Acid

以下,對勞丹酸的製造例1進行記載。 Hereinafter, Production Example 1 of Laudanic Acid will be described.

以下述式(S8)所示的化合物作為起始物質,經由下述式(S9)、式(S10)所示的化合物,製造下述試驗中所使用的下述式(S4)所示的勞丹酸。此外,下述式(S8)中的波線對於雙鍵表示為E體、Z體或該等的混合物。 By using the compound represented by the following formula (S8) as a starting material, the compound represented by the following formula (S4) and the formula (S10) is used to produce the following formula (S4) used in the following test. Salicylic acid. Further, the wave line in the following formula (S8) is represented by a double bond as an E body, a Z body, or a mixture thereof.

向安裝有排水管與溫度計的2L的反應容器中添加所述式(S8)的一級烯丙醇的1,2,4-三甲基苯溶液690.68g。在氮氣環境下且31℃下,將二氯(對異丙基甲苯)釕(II)(Dichloro(p-Cymene)ruthenium(II))21.733g及三(4-甲氧基苯基)膦23.93g添加至反應容器中。將反應溶液在170℃~180℃下加熱2小時,進行醛的氧化反應。其後,冷卻至46℃,藉此使反應停止。藉由高效液相層析法(High Performance Liquid Chromatography,HPLC)對反應停止後的反應溶液的一部分進行分析,決定本反應的轉化率及產率(轉化率:100%,產率:61.95%)。將包含所述式(S9)的醛的1,2,4-三甲基苯溶液710g在不純化的情況下用於下一反應。 690.68 g of a 1,2,4-trimethylbenzene solution of the primary allyl alcohol of the formula (S8) was added to a 2 L reaction vessel equipped with a drain pipe and a thermometer. Dichloro(p-Cymene)ruthenium(II)) 21.733g and tris(4-methoxyphenyl)phosphine 23.93 of dichloro(p-Cymene)ruthenium(II) under nitrogen atmosphere at 31 °C g is added to the reaction vessel. The reaction solution was heated at 170 ° C to 180 ° C for 2 hours to carry out an oxidation reaction of the aldehyde. Thereafter, it was cooled to 46 ° C, thereby stopping the reaction. A part of the reaction solution after the reaction was stopped was analyzed by High Performance Liquid Chromatography (HPLC) to determine the conversion and yield of the reaction (conversion: 100%, yield: 61.95%) . 710 g of a 1,2,4-trimethylbenzene solution containing the aldehyde of the formula (S9) was used in the next reaction without purification.

向安裝有溫度計的2L的反應容器中添加所述式(S9) 的醛的1,2,4-三甲基苯溶液710g、及1,2,4-三甲基苯300g、乙酸0.2g、胺磺酸(H2NSO2OH)54.57g、水27.28g。將混合物在乾冰-丙酮浴中冷卻至-5℃。繼而,在-8℃~-4℃之間歷時100分鐘滴加藉由使80%亞氯酸鈉(NaClO2)63.54g溶解於水190.6g中而製備的水溶液。於該溫度下反應2小時後,繼而在-5℃~-3℃下歷時30分鐘滴加20%Na2SO3水溶液425g,其後在40℃~50℃下攪拌30分鐘而使過氧化物完全分解。分液後,利用5%食鹽水250g洗滌2次,獲得所述式(S10)的羥基羧酸的1,2,4-三甲基苯溶液1000g。將其在不純化的情況下用於下一反應。 710 g of a 1,2,4-trimethylbenzene solution of the aldehyde of the formula (S9), 300 g of 1,2,4-trimethylbenzene, and 0.2 g of acetic acid were added to a 2 L reaction vessel equipped with a thermometer. Aminesulfonic acid (H 2 NSO 2 OH) 54.57 g and water 27.28 g. The mixture was cooled to -5 °C in a dry ice-acetone bath. Then, an aqueous solution prepared by dissolving 80% of sodium chlorite (NaClO 2 ) 63.54 g in water of 190.6 g was added dropwise over -8 ° C to -4 ° C over 100 minutes. After reacting at this temperature for 2 hours, 425 g of a 20% aqueous solution of Na 2 SO 3 was added dropwise thereto at -5 ° C to -3 ° C for 30 minutes, and then stirred at 40 ° C to 50 ° C for 30 minutes to cause peroxide. Completely decomposed. After liquid separation, the mixture was washed twice with 250 g of 5% brine to obtain 1000 g of a 1,2,4-trimethylbenzene solution of the hydroxycarboxylic acid of the formula (S10). This was used in the next reaction without purification.

向安裝有排水管與溫度計的2L的反應容器中添加所述式(S10)的羥基羧酸的1,2,4-三甲基苯溶液1000g、20%硫酸水溶液2.68g,在加熱回流下且170℃~176℃下一面排水一面進行3小時脫水反應。反應結束後,將反應溶液冷卻,添加28%甲醇鈉甲醇溶液74.9g,使作為產物的羧酸形成鈉鹽。向其中添加水154g,結果分離為上層的中性組分與下層的羧酸的鈉鹽組分。將上層去除後,利用庚烷200mL將下層洗滌2次。向下層添加庚烷200mL及20%硫酸水溶液95.2g,一面使羧酸的鈉鹽轉化為羧酸一面利用庚烷萃取羧酸。藉由將溶劑在減壓下進行加熱而回收產物後,進行產物的減壓蒸餾,藉此獲得所述的式(S4)所示的羧酸的雙鍵位置異構體混合物100g。產率為35.8%。 1000 g of a 1,2,4-trimethylbenzene solution of the hydroxycarboxylic acid of the formula (S10) and 2.68 g of a 20% sulfuric acid aqueous solution were added to a 2 L reaction vessel equipped with a drain pipe and a thermometer, and heated under reflux. The dehydration reaction was carried out for 3 hours while draining from 170 ° C to 176 ° C. After completion of the reaction, the reaction solution was cooled, and 74.9 g of a 28% sodium methoxide methanol solution was added to form a sodium salt as a carboxylic acid as a product. 154 g of water was added thereto, and as a result, it was separated into a neutral component of the upper layer and a sodium salt component of the lower layer of the carboxylic acid. After the upper layer was removed, the lower layer was washed twice with heptane 200 mL. To the lower layer, 200 mL of heptane and 95.2 g of a 20% aqueous sulfuric acid solution were added, and the carboxylic acid was extracted with heptane while converting the sodium salt of the carboxylic acid into a carboxylic acid. After recovering the product by heating the solvent under reduced pressure, the product was subjected to vacuum distillation to obtain 100 g of a double bond position isomer mixture of the carboxylic acid represented by the above formula (S4). The yield was 35.8%.

以下,對勞丹酸的製造例2進行記載。 Hereinafter, Production Example 2 of Laudanic Acid will be described.

對市售的勞丹脂原精(labdanum absolute)10g進行分子蒸 餾,收集沸點180℃~220℃/13.3Pa的餾分(以下,稱為Ext-1)4.3g。對該Ext-1進行解析,結果可知Ext-1中包含勞丹-8-烯-15-酸(式(S5))、勞丹-7-烯-15-酸(式(S6))、勞丹-8(17)-烯-15-酸(式(S7))。 Molecular steaming of commercially available labdanum absolute 10g Distillation was carried out, and 4.3 g of a fraction having a boiling point of 180 ° C to 220 ° C / 13.3 Pa (hereinafter referred to as Ext-1) was collected. When this Ext-1 was analyzed, it was found that Ext-1 contains labdan-8-ene-15-acid (formula (S5)), labdan-7-ene-15-acid (formula (S6)), labor Dan-8(17)-ene-15-acid (formula (S7)).

<試驗A>勞丹酸類抑制神經醯胺類的結晶化.析出的效果的確認(實施例A7) <Test A> Laudanic acid inhibits the crystallization of neuralamines. Confirmation of the effect of precipitation (Example A7)

在50mL的燒杯(beaker)中,將1.0g的神經醯胺2、9.0g的製造例1的勞丹酸在無溶劑下混合。對如此製備的組成物進行下述(1)及(2)的實驗。將組成物的詳情示於表1(此外,表1中以重量比例表示組成)。 In a 50 mL beaker, 1.0 g of neuropterin 2 and 9.0 g of the labyrin acid of Production Example 1 were mixed without a solvent. The following preparations (1) and (2) were subjected to the compositions thus prepared. The details of the composition are shown in Table 1 (in addition, the composition is represented by weight ratio in Table 1).

(1)神經醯胺類結晶析出溫度的測定 (1) Determination of crystallization temperature of neural guanamine

將所製備的組成物加熱至120℃,製成透明的溶液(均勻的溶液)後,一面攪拌一面冷卻至40℃。以目視觀察該過程中神經醯胺類的結晶化的情況,在開始觀察到白色結晶物的情況下,測定此時的溫度作為神經醯胺類結晶析出溫度,將至40℃為止未確認到白色結晶物的情況設為無神經醯胺類的結晶析出(後述的表1中以「○」表示)。將結果示於表1。此外,冷卻後,幾乎觀察不到勞丹酸類的結晶化。 The prepared composition was heated to 120 ° C to prepare a transparent solution (homogeneous solution), and then cooled to 40 ° C while stirring. The crystallization of the neuropterin in the process was visually observed. When the white crystal was observed, the temperature at this time was measured as the temperature of the ceramide precipitation, and no white crystal was observed until 40 °C. In the case of the substance, it is assumed that there is no crystal precipitation of a neurolamine (indicated by "○" in Table 1 to be described later). The results are shown in Table 1. Further, after cooling, almost no crystallization of the labyrin acid was observed.

(2)顯微鏡觀察 (2) Microscopic observation

使用直立式顯微鏡(Upright Microscope)(奧林巴斯(Olympus)公司製造)在倍率20倍、曝光時間1/300秒的條件下在偏光下對成為40℃的所述組成物進行顯微鏡觀察。此外,在偏光下神經醯 胺類在組成物中以結晶的形式存在的情況下,作為白色的光亮物而被觀察到。將結果的一部分示於圖1(a)、圖1(b)。 The composition which was 40 ° C was observed under a polarizing condition using an Upright Microscope (manufactured by Olympus Co., Ltd.) under the conditions of a magnification of 20 times and an exposure time of 1/300 second. In addition, under the polarized light, the neural crest When the amine is present in the form of crystals in the composition, it is observed as a white bright material. A part of the results is shown in Fig. 1 (a) and Fig. 1 (b).

(實施例A1~實施例A6、實施例A8~實施例A14、比較例A1~比較例A4) (Examples A1 to A6, Examples A8 to A14, Comparative Example A1 to Comparative Example A4)

除設為表1所示的組成的方面以外,以與實施例A7相同的方式製備組成物,進行(1)及(2)的實驗。將結果示於表1。 The composition was prepared in the same manner as in Example A7 except that the composition shown in Table 1 was used, and the experiments of (1) and (2) were carried out. The results are shown in Table 1.

根據<試驗A>的結果可明確,勞丹酸類使神經醯胺類溶解的能力高,顯示出抑制神經醯胺類的結晶化.析出的效果。 According to the results of <Test A>, it is clear that the labdanic acid has a high ability to dissolve the neural amines and shows inhibition of the crystallization of the neural amines. The effect of precipitation.

<試驗B>化妝料中勞丹酸類抑制神經醯胺類的結晶化.析出的效果的確認 <Test B> Lauranic acid inhibits the crystallization of neural amides in cosmetics. Confirmation of the effect of precipitation

(實施例B1) (Example B1)

將神經醯胺II、製造例1的勞丹酸、PEG60氫化蓖麻油混合,將該混合物加熱至100℃,製成均勻的溶液(溶液A)。向該溶液中添加1,3-丁二醇、乙醇,一面保持為50℃,一面以變得均勻的方式混合(溶液B)。向純化水中添加溶液B,將溶液緩慢地冷卻至40℃。如此,製備除神經醯胺類及勞丹酸類以外亦進而包含化妝料成分的化妝料(化妝水)。將化妝料(化妝水)的詳情示於表2(此外,表2中以重量%表示組成)。 The neuropterin II, the labranic acid of Production Example 1, and the PEG 60 hydrogenated castor oil were mixed, and the mixture was heated to 100 ° C to prepare a homogeneous solution (solution A). To the solution, 1,3-butanediol and ethanol were added, and while being kept at 50 ° C, they were mixed so as to be uniform (solution B). Solution B was added to the purified water, and the solution was slowly cooled to 40 °C. In this manner, a cosmetic (make lotion) containing a cosmetic component in addition to the nervous steroids and the labousuric acid is prepared. The details of the cosmetic (makeup) are shown in Table 2 (in addition, the composition is expressed by weight % in Table 2).

(透光率測定) (Light transmittance measurement)

對所製備的組成物進行透光率測定的實驗。將所製備的組成物加熱至40℃,製成透明的溶液(均勻的溶液)後,在室溫下放置。使用分光光度計(UV-2500PC UV-VIS REDCORDING SPECTROPHOTOMETER,島津製作所公司製造)測定剛放置後、及自放置開始起3天後在550nm下的透光率。測定中使用光程長度10mm(光程寬度10mm)的玻璃光槽(glass cell),使用純化水作為參照試樣。藉由下述判定基準對透光率進行判定。將結果示於表2。 An experiment for measuring the transmittance of the prepared composition was carried out. The prepared composition was heated to 40 ° C to prepare a transparent solution (homogeneous solution), and then allowed to stand at room temperature. The light transmittance at 550 nm immediately after standing and after 3 days from the start of standing was measured using a spectrophotometer (UV-2500PC UV-VIS REDCORDING SPECTROPHOTOMETER, manufactured by Shimadzu Corporation). A glass cell having an optical path length of 10 mm (optical path width: 10 mm) was used for the measurement, and purified water was used as a reference sample. The light transmittance was determined by the following criteria. The results are shown in Table 2.

[判定基準](判定結果:判定內容) [Judgement criteria] (judgment result: judgment content)

×:小於10% ×: less than 10%

△:30%以上~小於50% △: 30% or more ~ less than 50%

○:50%以上~小於70% ○: 50% or more ~ less than 70%

◎:70%以上 ◎: 70% or more

(實施例B2~實施例B9) (Example B2 to Example B9)

除設為表2所示的組成的方面以外,以與實施例B1相同的方式製備化妝料,進行透光率測定的實驗。將結果示於表2。 A cosmetic was prepared in the same manner as in Example B1 except that the composition shown in Table 2 was used, and an experiment for measuring the light transmittance was carried out. The results are shown in Table 2.

根據<試驗B>的結果可明確,在除神經醯胺類及勞丹酸類以外亦進而包含化妝料成分的化妝料中,勞丹酸類的使神經醯胺類溶解的能力亦高,亦顯示出抑制神經醯胺類的結晶化.析出的效果。 According to the results of <Test B>, it is clear that in the cosmetics containing the cosmetic component in addition to the neuropterin and the labrinic acid, the ability of the labyrin acid to dissolve the neural amines is also high, and it is also shown. Inhibits the crystallization of neural steroids. The effect of precipitation.

<試驗C>化妝料的皮膚的障壁功能改善效果的確認 <Test C> Confirmation of the improvement effect of the barrier function of the skin of the cosmetic

(實施例C1) (Example C1)

與<試驗B>同樣地,使用表3所示的成分,製備除神經醯胺類及勞丹酸類以外亦進而包含化妝料成分的化妝料。將化妝料的詳情示於表3(此外,表3中以重量比率表示組成)。 In the same manner as in <Test B>, the components shown in Table 3 were used to prepare a cosmetic containing a cosmetic component in addition to the nervous amines and the labrinic acid. The details of the cosmetic are shown in Table 3 (in addition, the composition is expressed by weight ratio in Table 3).

對所製備的化妝料,進行確認障壁功能改善效果的實驗。利用丙酮醚對健康的20代~30代的男性10名的上臂部進行處理,形成粗糙的皮膚。將所製備的化妝料對該粗糙的皮膚以每單臂早晚2次連續使用1週。使用水分蒸散計(Vapometer,德風(Delfin)公司製造)測定皮膚的水分蒸散量(TEWL)。此外,水分蒸散量是以將未對粗糙的皮膚實施任何處置的情況下的水分蒸發量設為100的情況下的相對值算出。基於所述相對值的平均,藉由下述判定基準對化妝料的保濕效果進行判定。將結果示於表3。 An experiment for confirming the effect of improving the barrier function was performed on the prepared cosmetic. The upper arm of 10 healthy males of 20 to 30 generations was treated with acetone ether to form rough skin. The prepared cosmetic material was continuously applied to the rough skin twice a day for two times per arm. The amount of moisture evapotranspiration (TEWL) of the skin was measured using a moisture evapotranspiration meter (Vapometer, manufactured by Delfin). In addition, the amount of moisture evapotranspiration is calculated as a relative value when the amount of water evaporation in the case where any treatment is not performed on rough skin is set to 100. Based on the average of the relative values, the moisturizing effect of the cosmetic is determined by the following criteria. The results are shown in Table 3.

[判定基準](判定結果:判定內容) [Judgement criteria] (judgment result: judgment content)

◎:相對值的平均小於80 ◎: The average value of relative values is less than 80

○:相對值的平均為80以上且小於90 ○: The average value of the relative values is 80 or more and less than 90

△:相對值的平均為90以上且小於100 △: The average value of the relative values is 90 or more and less than 100

×:相對值的平均為100以上 ×: The average value of relative values is 100 or more

(比較例C1、比較例C2) (Comparative Example C1, Comparative Example C2)

除設為表3所示的組成的方面以外,與實施例C1同樣地製備化妝料,進行確認障壁功能改善效果的實驗。將結果示於表3。 In addition to the composition shown in Table 3, a cosmetic was prepared in the same manner as in Example C1, and an experiment for confirming the effect of improving the barrier function was performed. The results are shown in Table 3.

根據<試驗C>的結果可明確,除神經醯胺類及勞丹酸類以外亦進而包含化妝料成分的化妝料亦保持神經醯胺類原本所具備的皮膚的障壁功能改善效果。 According to the results of <Test C>, it is clear that the cosmetic containing the cosmetic component in addition to the neuropterin and the labrinic acid also maintains the barrier function improving effect of the skin originally provided by the neurosteroid.

<試驗D> <Test D>

以下,表示依據本發明的組成物、及含有依據本發明的組成 物的化妝料及皮膚外用劑的配方例。此外,下述的實施例D1~實施例D4中的%是將總量設為100質量%的值。 Hereinafter, the composition according to the present invention and the composition according to the present invention are shown A formulation example of a cosmetic and an external preparation for skin. Further, % in the following Examples D1 to D4 is a value in which the total amount is 100% by mass.

(實施例D1) (Embodiment D1)

使用下述所示的成分製備美容液。 A cosmetic liquid was prepared using the ingredients shown below.

將所述成分1~成分10混合,將該混合物加熱至90℃,製成均勻的溶液(溶液A)。繼而,將所述成分11~成分16混合,將該混合物加熱至70℃,製成均勻的溶液(溶液B)。向溶液A中添加溶液B,在70℃下乳化(溶液C)。將溶液C冷卻至40℃,向其中添加所述17,充分混合而獲得美容液。 The components 1 to 10 were mixed, and the mixture was heated to 90 ° C to prepare a homogeneous solution (solution A). Then, the components 11 to 16 were mixed, and the mixture was heated to 70 ° C to prepare a homogeneous solution (solution B). Solution B was added to solution A and emulsified at 70 ° C (solution C). The solution C was cooled to 40 ° C, and the 17 was added thereto, and thoroughly mixed to obtain a cosmetic liquid.

對所製備的美容液,進行與<試驗B>中的透光率測定的實驗相同的實驗、及與<試驗C>中的確認障壁功能改善效果的實驗相同的實驗。可知實施例D1的美容液的抑制神經醯胺類的結晶化.析出的效果、及障壁功能改善效果優異。 The prepared beauty liquid was subjected to the same experiment as the experiment of measuring the light transmittance in <Test B>, and the same experiment as the experiment for confirming the effect of improving the barrier function in <Test C>. It can be seen that the cosmetic liquid of Example D1 inhibits the crystallization of neuralamines. The effect of precipitation and the effect of improving barrier function are excellent.

(實施例D2) (Example D2)

使用下述所示的成分而製備乳液。 The emulsion was prepared using the ingredients shown below.

將所述成分1~成分10混合,將該混合物加熱至90℃,製成均勻的溶液(溶液A)。繼而,將所述成分11~成分14混合,將該混合物加熱至70℃,製成均勻的溶液(溶液B)。向溶液B中添加溶液A,冷卻至室溫,向其中添加所述15、16,充分地混合而獲得乳液。 The components 1 to 10 were mixed, and the mixture was heated to 90 ° C to prepare a homogeneous solution (solution A). Then, the components 11 to 14 were mixed, and the mixture was heated to 70 ° C to prepare a homogeneous solution (solution B). Solution A was added to Solution B, cooled to room temperature, and the 15 and 16 were added thereto, and sufficiently mixed to obtain an emulsion.

對所製備的乳液,進行觀察神經醯胺類的結晶化.析出的情況的實驗、及與<試驗C>中的確認障壁功能改善效果的實驗相同的實驗。可知實施例D2的乳液的抑制神經醯胺類的結晶化.析出的效果、及障壁功能改善效果優異。 4. For the prepared emulsion, observe the crystallization of neural amines. The experiment of the case of precipitation and the experiment similar to the experiment which confirmed the effect of the barrier function improvement in <Test C>. It can be seen that the emulsion of Example D2 inhibits the crystallization of neural amines. The effect of precipitation and the effect of improving barrier function are excellent.

(實施例D3) (Example D3)

使用下述所示的成分而製備固體狀潤唇膏。 A solid lip balm was prepared using the ingredients shown below.

將所述成分1~成分7混合,將該混合物加熱至100℃,製成均勻的溶液(溶液A)。繼而,向溶液A中添加所述成分8~成分10,充分混合(溶液B)。將溶液B流入至金皿中,進行冷卻固化,獲得固體狀潤唇膏。 The components 1 to 7 were mixed, and the mixture was heated to 100 ° C to prepare a homogeneous solution (solution A). Then, the component 8 to the component 10 were added to the solution A, and the mixture was sufficiently mixed (solution B). The solution B was poured into a gold dish, and solidified by cooling to obtain a solid lip balm.

對所製備的固體狀潤唇膏,進行觀察神經醯胺類的結晶化.析出的情況的實驗、及確認皮膚的障壁功能改善的情況的實驗。可知實施例D3的固體狀潤唇膏的抑制神經醯胺類的結晶化.析出的效果、及障壁功能改善效果優異。 4. For the prepared solid lip balm, observe the crystallization of neural amines. Experiments in the case of precipitation and experiments to confirm the improvement of the barrier function of the skin. It can be seen that the solid lip balm of Example D3 inhibits the crystallization of neural amines. The effect of precipitation and the effect of improving barrier function are excellent.

(實施例D4) (Example D4)

使用下述所示的成分製備防曬霜。 A sunscreen was prepared using the ingredients shown below.

將所述成分1~成分7混合,將該混合物加熱至70℃,使之加熱膨潤(溶液A)。繼而,將所述成分8~成分12混合,將該混合物加熱至70℃,製成均勻的溶液(溶液B)。向溶液A中添加溶液B而進行乳化,其後冷卻至室溫(溶液C)。向溶液C中添加所述成分13、成分14,充分混合(溶液D)。向溶液D中添加所述成分15,充分混合而獲得防曬霜。 The components 1 to 7 were mixed, and the mixture was heated to 70 ° C to heat and swell (solution A). Then, the components 8 to 12 were mixed, and the mixture was heated to 70 ° C to prepare a homogeneous solution (solution B). The solution B was added to the solution A to be emulsified, and then cooled to room temperature (solution C). The component 13 and the component 14 were added to the solution C, and sufficiently mixed (solution D). The component 15 was added to the solution D and thoroughly mixed to obtain a sunscreen.

對所製備的防曬霜,進行觀察神經醯胺類的結晶化.析出的情況的實驗、及確認皮膚的障壁功能改善的情況的實驗。可知實施例D4的防曬霜的抑制神經醯胺類的結晶化.析出的效果、及障壁功能改善效果優異。 4. For the prepared sunscreen, observe the crystallization of neural amines. Experiments in the case of precipitation and experiments to confirm the improvement of the barrier function of the skin. It can be seen that the sunscreen of Example D4 inhibits the crystallization of neuralamines. The effect of precipitation and the effect of improving barrier function are excellent.

[產業上之可利用性] [Industrial availability]

根據本發明的組成物,可抑制組成物中神經醯胺類結晶 化而析出,從而可提高神經醯胺類在組成物中的穩定性。根據本發明的化妝料,可抑制化妝料中神經醯胺類結晶化而析出,從而可提高神經醯胺類在化妝料中的穩定性。 According to the composition of the present invention, inhibition of ceramide crystallization in the composition It is precipitated, thereby improving the stability of the neuropterin in the composition. According to the cosmetic of the present invention, it is possible to suppress the precipitation of the neuropterin in the cosmetic material, thereby improving the stability of the neuropterin in the cosmetic.

Claims (4)

一種組成物,其特徵在於:包含神經醯胺類與勞丹酸類。 A composition comprising a neuropterin and a labousuric acid. 如申請專利範圍第1項所述的組成物,其中所述勞丹酸類相對於所述神經醯胺類的比例為0.01~100。 The composition according to claim 1, wherein the ratio of the labousanic acid to the neurosteroid is 0.01 to 100. 如申請專利範圍第2項所述的組成物,其中所述勞丹酸類相對於所述神經醯胺類的比例為0.1~50。 The composition according to claim 2, wherein the ratio of the labousanic acid to the neurosteroid is from 0.1 to 50. 一種化妝料,其特徵在於:包含如申請專利範圍第1項至第3項中任一項所述的組成物。 A cosmetic composition comprising the composition according to any one of claims 1 to 3.
TW104109858A 2014-03-28 2015-03-27 Composition, cosmetic material, and crystallization and precipitation inhibition method of neural guanamine TWI668014B (en)

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