KR100760148B1 - Cosmetic composition for stabilizing alpha-lipoic acid - Google Patents

Cosmetic composition for stabilizing alpha-lipoic acid Download PDF

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KR100760148B1
KR100760148B1 KR1020060067441A KR20060067441A KR100760148B1 KR 100760148 B1 KR100760148 B1 KR 100760148B1 KR 1020060067441 A KR1020060067441 A KR 1020060067441A KR 20060067441 A KR20060067441 A KR 20060067441A KR 100760148 B1 KR100760148 B1 KR 100760148B1
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South Korea
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poe
alpha
lipoic acid
cosmetic composition
glyceryl monostearate
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KR1020060067441A
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Korean (ko)
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김병준
곽상훈
윤세영
강상진
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주식회사 엘지생활건강
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    • 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
    • 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
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
    • 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
    • A61Q19/08—Anti-ageing preparations
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers

Abstract

A cosmetic composition for stabilizing alpha-lipoic acid is provided to maintain effects for a long period of time by preventing changes of smell and color of alpha-lipoic acid caused by binding with thiol, thereby being useful for skin whitening, skin wrinkle prevention, oxidation inhibition and body sliming. A cosmetic composition comprises: 0.01-20 wt.% of alpha-lipoic acid; 0.1-30 wt.% of polyol as a stabilizer of alpha-lipoic acid selected from propylene glycol, glycerin, 1,3-butylene glycol, 1,3-butandiol and sorbitol; and 0.01-10 wt.% of non-ionic surfactant selected from POE(polyoxyethylene) sorbitan fatty acid ester, POE alkyl ether, POE hydrogenated ester oil, POE(10) octyldodecyl ether, POE(15) octyldodecyl ether, POE(20) octyldodecyl ether, POE(30) octyldodecyl ether, POE(15) glyceryl monostearate, POE(20) glyceryl monostearate, POE(25) glyceryl monostearate and POE(30) glyceryl monostearate, and is formulated as skin, lotion, cream, foundation or essence.

Description

알파-리포산을 안정화시킨 화장료 조성물{COSMETIC COMPOSITION FOR STABILIZING ALPHA-LIPOIC ACID}Cosmetic composition which stabilized alpha-lipoic acid {COSMETIC COMPOSITION FOR STABILIZING ALPHA-LIPOIC ACID}

본 발명은 알파-리포산을 안정화시킨 화장료 조성물에 관한 것으로, 보다 상세하게는 폴리올류와 비이온성 계면활성제를 일정한 비율로 혼합함으로써 알파-리포산이 변취, 변색 등 불안정화되는 것을 방지하여 유화물에서 안정화시킨 혼합 화장료 조성물에 관련된다.The present invention relates to a cosmetic composition stabilized alpha-lipoic acid, and more particularly, by mixing a polyol and a nonionic surfactant in a constant ratio to prevent the destabilization of the alpha-lipoic acid, such as odor, discoloration, etc. It relates to a cosmetic composition.

알파-리포산(α-lipoic acid)은 티옥트산(thioctic acid), 6,8-디티옥탄산, 1,2-디에틸렌-3 펜타노산 등의 다양한 이름을 갖고 있다. 알파-리포산은 당뇨병에 수반되는 제 증상들을 치료하는 효과를 가질 뿐 아니라, 체내에서 항산화 물질들의 수치를 건강한 상태로 유지시키는 데에도 중요한 역할을 수행하는 것으로 알려져 있다. 또한, 글루타치온과 비타민 C, E 등의 생성을 촉진하는 작용도 지닌 것으로 알려졌다. 최근에는 세포내 에너지 증가제(대한민국 특허등록 10-0427637), 지방세포 분화 억제(The Journal of Biological Chemistry, α-lipoic acid inhihits adipocyte differentiation by regulating pro-adipogenic transcription factors via mitogen-activated protein kinase pathways, vol. 278, No. 37, 2003, 34823- 34833), 혈관 내 지질류 증가 억제(대한민국 특허공개 10-2004-0067312)로 혈관 질환의 예방 및 치료제로서, 그리고 체중 감소용 식품, 비만 치료 식품으로도 주목받고 있다.Alpha-lipoic acid has various names such as thioctic acid, 6,8-dithiooctanoic acid and 1,2-diethylene-3 pentanoic acid. Alpha-lipoic acid is known to not only have the effect of treating the symptoms associated with diabetes, but also plays an important role in maintaining a healthy state of antioxidants in the body. In addition, glutathione and vitamins C, E, etc. are known to have the action of promoting the production. Recently, the Journal of Biological Chemistry , α-lipoic acid inhihits adipocyte differentiation by regulating pro-adipogenic transcription factors via mitogen-activated protein kinase pathways, vol 278, No. 37, 2003, 34823-34833), inhibiting the increase of vascular lipids (Korean Patent Publication No. 10-2004-0067312), as a preventive and therapeutic agent for vascular diseases, and as a weight loss food and an obesity food. It is attracting attention.

한편, 알파-리포산은 화장품에 사용되는 수용액에 대해서는 낮은 용해 특성을 가지며, 일광 하에서나 시간 경과에 따라 티올(thiol)로 결합 분리되어 변취 및 변색되는 문제, 그리고 황 성분에 의한 고유취의 문제가 있어 화장품 성분으로 사용하는 데에는 어려움이 있었다. 즉, 알파-리포산은 우수한 효능에도 불구하고 변색, 변취에 대한 낮은 안정도 때문에 실제적인 응용에 제한이 있었던 바, 그 안정도를 지키고자 하는 연구가 다양하게 진행되어왔다.On the other hand, alpha-lipoic acid has low solubility characteristics in aqueous solutions used in cosmetics, has a problem of discoloration and discoloration by dissolving and discoloring as thiols under daylight or over time, and a problem of high odor due to sulfur component. There was a difficulty in using it as a cosmetic ingredient. That is, alpha-lipoic acid has been limited in practical applications because of its low stability against discoloration and odor, despite its excellent efficacy, and various studies have been conducted to protect its stability.

지금까지 진행되었던 알파-리포산의 안정화 방법으로는, 구체적인 예로서, 시클로덱스트린(cyclodexrtrin) 등의 다공성 폴리머에 함유시켜 안정화(대한민국 특허공개 10-2005-0039927)하거나, 솔리드 리피드 나노파티클을 이용한 캡슐화 방법 등이 보고되어있다(Souto EB, Muller RH, Gohla S., J. Microencapsul . 2005, Sep; 22(6), 581-92A, Novel approach based on lipid nanoparticles(SLN) for topical delivery of alpha-lipoic acid).As a method of stabilizing alpha-lipoic acid, which has been carried out so far, as a specific example, it is contained in a porous polymer such as cyclodexrtrin and stabilized (Korean Patent Publication No. 10-2005-0039927), or an encapsulation method using solid lipid nanoparticles. (Souto EB, Muller RH, Gohla S., J. Microencapsul . 2005, Sep; 22 (6), 581-92A, Novel approach based on lipid nanoparticles (SLN) for topical delivery of alpha-lipoic acid). ).

그러나, 다양한 환경 인자들로 인해 상기에서 언급한 방법으로 알파-리포산의 특이취나 변색, 변취 등 안정성 문제를 해결하는 것은 매우 어려웠다.However, due to various environmental factors, it was very difficult to solve the stability problems such as the specific odor, discoloration, and discoloration of alpha-lipoic acid by the aforementioned method.

이에, 본 발명자들은 상기와 같은 문제점을 해결하기 위해 알파-리포산을 안정화시킬 수 있는 방법을 연구한 결과, 폴리올류와 비이온성 계면활성제를 일정한 비율로 혼합하여 사용함으로써 변취, 변색 등 안정성 문제를 해결할 수 있는 방법 을 발견하여 본 발명을 완성하게 되었다.Therefore, the present inventors have studied a method for stabilizing alpha-lipoic acid to solve the above problems, by using a mixture of polyols and nonionic surfactants in a constant ratio to solve the stability problems such as discoloration, discoloration The present invention has been accomplished by finding a method that can

본 발명의 목적은 화장료 조성물에서 알파-리포산이 변취, 변색에 의해 불안정화되는 것을 방지하여 안정화시킨 혼합 화장료 조성물을 제공하고자 하는 것이다.It is an object of the present invention to provide a mixed cosmetic composition stabilized by preventing alpha-lipoic acid from being destabilized by odor and discoloration in the cosmetic composition.

상기의 목적을 달성하기 위하여 본 발명에서는, 알파-리포산을 포함하는 화장료 조성물에 있어서, 알파-리포산의 안정화제로서 조성물 총 중량에 대해서 폴리올 0.1∼30 중량% 및 비이온성 계면활성제 0.01∼10 중량%를 포함하는 화장료 조성물을 제공한다.In order to achieve the above object, in the present invention, in the cosmetic composition comprising alpha-lipoic acid, 0.1 to 30% by weight of polyol and 0.01 to 10% by weight of nonionic surfactant based on the total weight of the composition as a stabilizer of alpha-lipoic acid It provides a cosmetic composition comprising a.

이하, 본 발명을 구체적으로 설명한다.Hereinafter, the present invention will be described in detail.

본 발명의 조성물에 사용되는 알파-리포산은 특별히 한정되지는 않지만, 알파-리포산과 분해된 디하이드로리포산(DHLA, dihydrolipoic acid)으로서, 하기 화학식 1 및 화학식 2로 표시되는 2 종과 이들의 유도체들이 있다.The alpha-lipoic acid used in the composition of the present invention is not particularly limited, but is alpha-lipoic acid and dehydrolyzed dihydrolipoic acid (DHLA, dihydrolipoic acid). have.

Figure 112006051341150-pat00001
Figure 112006051341150-pat00001

Figure 112006051341150-pat00002
Figure 112006051341150-pat00002

이러한 알파-리포산의 첨가량은 조성물 총 중량에 대하여 0.01∼20 중량%인 것이 바람직하다.The amount of such alpha-lipoic acid added is preferably 0.01 to 20% by weight based on the total weight of the composition.

본 발명의 화장료 조성물에서 폴리올과 비이온성 계면활성제의 혼합계는 조성물 총 중량에 대해 0.1∼40 중량%의 양으로 함유하는 것이 바람직하다. 0.1 중량% 미만으로 사용할 경우에는 알파-리포산의 변취, 변색 등과 같은 불안정화를 막을 수 없으며, 40 중량%를 초과하는 경우에는 변취, 변색, 용해도, 결정화 등 화장료에 적합하지 않다.In the cosmetic composition of the present invention, the mixed system of the polyol and the nonionic surfactant is preferably contained in an amount of 0.1 to 40% by weight based on the total weight of the composition. When used in less than 0.1% by weight can not prevent destabilization, such as discoloration, discoloration, such as alpha-lipoic acid, if it exceeds 40% by weight is not suitable for cosmetics such as odor, discoloration, solubility, crystallization.

또한, 본 발명의 화장료 조성물에서, 폴리올과 비이온성 계면활성제의 혼합비율은 1∼7:1∼5인 것이 바람직하고, 6∼7:1∼2인 것이 더욱 바람직하다.Moreover, in the cosmetic composition of this invention, it is preferable that the mixing ratio of a polyol and a nonionic surfactant is 1-7: 1-5, and it is more preferable that it is 6-7: 1-2.

본 발명의 화장료 조성물에 사용되는 폴리올은 프로필렌글리콜, 글리세린, 1,3-부틸렌글리콜, 1,3-부탄디올 및 솔비톨로 이루어지는 군으로부터 선택되는 적어도 1 종일 수 있다. The polyol used in the cosmetic composition of the present invention may be at least one member selected from the group consisting of propylene glycol, glycerin, 1,3-butylene glycol, 1,3-butanediol and sorbitol.

그리고, 비이온성 계면활성제는 POE(폴리옥시에틸렌) 솔비탄 지방산 에스테르, POE 알킬 에테르(LA), POE 수소화 에스테르 오일, POE(10) 옥틸도데실 에테르, POE(15) 옥틸도데실 에테르, POE(20) 옥틸도데실 에테르, POE(30) 옥틸도데실 에테 르, POE(15) 글리세릴 모노스테아레이트, POE(20) 글리세릴 모노스테아레이트, POE(25) 글리세릴 모노스테아레이트 및 POE(30) 글리세릴 모노스테아레이트로 이루어지는 군으로부터 선택되는 적어도 1종일 수 있다.The nonionic surfactants include POE (polyoxyethylene) sorbitan fatty acid esters, POE alkyl ethers (LA), POE hydrogenated ester oils, POE (10) octyldodecyl ethers, POE (15) octyldodecyl ethers, POE ( 20) octyldodecyl ether, POE (30) octyldodecyl ether, POE (15) glyceryl monostearate, POE (20) glyceryl monostearate, POE (25) glyceryl monostearate and POE (30) ) Glyceryl monostearate may be at least one selected from the group consisting of.

한편, 본 발명의 화장료 조성물은 스킨, 로션, 크림, 파운데이션 및 에센스로 이루어진 군으로부터 선택된 어느 하나의 제형으로 형성될 수 있다.On the other hand, the cosmetic composition of the present invention may be formed of any one formulation selected from the group consisting of skin, lotion, cream, foundation and essence.

이하, 실시예를 들어 본 발명을 구체적으로 설명한다. 단, 이들 실시예는 당 업계에서 평균적인 지식을 가진 자에게 본 발명을 보다 완전하게 설명하기 위해서 제공되는 것으로, 여러 가지 다른 형태로 변형될 수 있으며, 본 발명의 범위가 이들만으로 한정되는 것으로 해석되어서는 안 된다.Hereinafter, an Example is given and this invention is demonstrated concretely. However, these examples are provided to more fully explain the present invention to those skilled in the art, and may be modified in many different forms and should be construed as limited to the scope of the present invention. It should not be.

실시예Example 1 내지 9 및  1 to 9 and 비교예Comparative example 1 내지 6 1 to 6

다음 표 1에 나타낸 조성으로 로션을 제조하였다. 표 1에서 단위는 중량%이다.The lotion was prepared with the composition shown in Table 1 below. In Table 1 the units are weight percent.

원료명Raw material name 실시예 1Example 1 실시예 2Example 2 실시예 3Example 3 비교예 1Comparative Example 1 비교예 2Comparative Example 2 콜레스테릴 에스테르Cholesteryl ester 2.02.0 2.02.0 2.02.0 2.02.0 2.02.0 세토스테아릴 알콜Cetostearyl alcohol 0.80.8 0.80.8 0.80.8 0.80.8 0.80.8 스테아린산Stearic acid 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 스쿠알란Squalane 8.08.0 8.08.0 8.08.0 8.08.0 8.08.0 정제 호호바유Purified Jojoba Oil 4.04.0 4.04.0 4.04.0 4.04.0 4.04.0 옥틸도데칸올Octyldodecanol 2.02.0 2.02.0 2.02.0 2.02.0 2.02.0 폴리솔베이트Polysorbate 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 세스퀴올레인산 솔비탄Sesquioleic acid sorbitan 0.50.5 0.50.5 0.50.5 0.50.5 0.50.5 카르복시비닐 폴리머Carboxyvinyl Polymer 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 트리에탄올아민Triethanolamine 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 방부제antiseptic 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 향료Spices 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 색소Pigment 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 프로필렌글리콜Propylene glycol 1010 1010 1010 1010 트윈 80 Twin 80 55 1010 2020 1010 알파 리포산Alpha lipoic acid 1One 1One 1One 1One 1One 정제수Purified water 합 100Total 100 합 100Total 100 합 100Total 100 합 100Total 100 합 100Total 100

다음 표 2에 나타낸 조성으로 에센스를 제조하였다. 표 2에서 단위는 중량%이다.To the essence was prepared in the composition shown in Table 2. In Table 2, the unit is weight percent.

원료명Raw material name 실시예 4Example 4 실시예 5Example 5 실시예 6Example 6 비교예 3Comparative Example 3 비교예 4Comparative Example 4 에탄올ethanol 6.06.0 6.06.0 6.06.0 6.06.0 6.06.0 메틸파라벤Methylparaben 0.10.1 0.10.1 0.10.1 0.10.1 0.10.1 폴리아크릴산Polyacrylic acid 5.05.0 5.05.0 5.05.0 5.05.0 5.05.0 하이드록시에틸셀룰로스Hydroxyethylcellulose 0.10.1 0.10.1 0.10.1 0.10.1 0.10.1 카르복시에틸셀룰로스Carboxyethylcellulose 0.10.1 0.10.1 0.10.1 0.10.1 0.10.1 트리에탄올아민Triethanolamine 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 에틸렌옥사이드Ethylene oxide 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 방부제antiseptic 5.05.0 5.05.0 5.05.0 5.05.0 5.05.0 향료Spices 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 프로필렌글리콜Propylene glycol 1010 1010 1010 1010 트윈 80 Twin 80 55 1010 2020 1010 알파 리포산Alpha lipoic acid 1One 1One 1One 1One 1One 정제수 Purified water 합 100Total 100 합 100Total 100 합 100Total 100 합 100Total 100 합 100Total 100

다음 표 3에 나타낸 조성으로 크림을 제조하였다. 표 3에서 단위는 중량%이다.To prepare a cream with the composition shown in Table 3. In Table 3, the unit is weight percent.

원료명Raw material name 실시예 7Example 7 실시예 8Example 8 실시예 9Example 9 비교예 5Comparative Example 5 비교예 6Comparative Example 6 마이크로스탈린 납Microstalin lead 2.02.0 2.02.0 2.02.0 2.02.0 2.02.0 세토스테아릴알콜Cetostearyl alcohol 0.80.8 0.80.8 0.80.8 0.80.8 0.80.8 스테아린산Stearic acid 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 스쿠알란Squalane 8.08.0 8.08.0 8.08.0 8.08.0 8.08.0 스테아린산글리세린Glycerin Stearate 4.04.0 4.04.0 4.04.0 4.04.0 4.04.0 옥틸도데칸올Octyldodecanol 2.02.0 2.02.0 2.02.0 2.02.0 2.02.0 폴리솔베이트Polysorbate 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 세스퀴올레인산소르비탄Sesquioleate sorbitan 0.50.5 0.50.5 0.50.5 0.50.5 0.50.5 유동파라핀Liquid paraffin 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 옥틸도데실미리스테이트Octyldodecyl Myristate 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 향료Spices 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 색소Pigment 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 프로필렌글리콜Propylene glycol 1010 1010 1010 1010 트윈 80 Twin 80 55 1010 2020 1010 알파 리포산Alpha lipoic acid 1One 1One 1One 1One 1One 정제수Purified water 합 100Total 100 합 100Total 100 합 100Total 100 합 100Total 100 합 100Total 100

효과시험예 1: 변취, 변색에 대한 테스트 Effect Test Example 1 Test for Deodorant and Discoloration

위 실시예 및 비교예에서 제조된 화장료 조성물의 변취, 변색에 대한 안정성을 시험하기 위하여, 각각의 조성물을 400 g씩 투명 유리 용기에 담아 실온에서 3 개월간 보관한 후 20 명에게 변색과 변취 정도를 확인하도록 하였다. 그 결과를 다음 표 4 및 5에 나타낸다.In order to test the stability against discoloration and discoloration of the cosmetic compositions prepared in the above Examples and Comparative Examples, each composition was stored in 400 g of a transparent glass container for 3 months at room temperature, and then the discoloration and discoloration of 20 people were measured. It was confirmed. The results are shown in Tables 4 and 5 below.

　 실시예 1Example 1 실시예 2Example 2 실시예 3Example 3 실시예 4Example 4 실시예 5Example 5 실시예 6Example 6 실시예 7Example 7 실시예 8Example 8 실시예 9Example 9 초기값Initial value 변취정도Odor 1One 00 1One 00 1One 1One 1One 1One 1One 변색정도Discoloration degree 00 00 00 00 00 00 00 00 00 3개월후3 months later 변취정도Odor 1One 1One 1One 1One 1One 1One 1One 1One 1One 변색정도Discoloration degree 00 00 00 1One 1One 00 1One 1One 00 6개월후6 months later 변취정도Odor 1One 1One 1One 1One 1One 1One 1One 1One 1One 변색정도Discoloration degree 1One 00 00 00 1One 1One 22 1One 1One

　 비교예1Comparative Example 1 비교예2Comparative Example 2 비교예3Comparative Example 3 비교예4Comparative Example 4 비교예5Comparative Example 5 비교예6Comparative Example 6 초기값Initial value 변취정도Odor 1One 1One 1One 1One 1One 1One 변색정도Discoloration degree 00 00 1One 00 1One 00 3개월후3 months later 변취정도Odor 1One 1One 44 1One 44 44 변색정도Discoloration degree 33 22 22 1One 22 1One 6개월후6 months later 변취정도Odor 22 22 44 33 44 44 변색정도Discoloration degree 44 44 33 33 33 33

위 표에서 판정기준은 다음과 같다:In the table above, the criteria are as follows:

(1) 변색정도(1) discoloration degree

0: 변화없음, 1: 극히 조금 변함, 2: 조금 변함, 3: 조금 심하게 변함,0: no change, 1: very little change, 2: little change, 3: little change,

4: 심하게 변함, 5: 극히 심하게 변함.4: severely changed, 5: extremely severe.

(2) 변취정도(2) the degree of odor

0: 변화없음, 1: 극히 조금 변함, 2: 조금 변함, 3: 조금 심하게 변함,0: no change, 1: very little change, 2: little change, 3: little change,

4: 심하게 변함, 5: 극히 심하게 변함.4: severely changed, 5: extremely severe.

상기 표 4 및 5의 결과에서 보듯이, 폴리올과 비이온성 계면활성제로 알파-리포산을 안정화시킨 실시예 1 내지 9의 화장료 조성물은, 비교예 1 내지 6의 화장료 조성물에 비하여 변취 및 변색에 대하여 안정하다. 따라서, 리포산에 의한 미백, 주름 제거, 항산화, 슬리밍 등의 효과가 기대된다. As shown in the results of Tables 4 and 5, the cosmetic compositions of Examples 1 to 9 stabilized alpha-lipoic acid with a polyol and a nonionic surfactant are more stable against discoloration and discoloration than the cosmetic compositions of Comparative Examples 1 to 6. Do. Therefore, the effects of lipoic acid whitening, wrinkle removal, antioxidant, slimming and the like are expected.

이상의 결과를 보다 정량적으로 확인하기 위해서, 고속액체크로마토그래피(HPLC)를 이용하여 실시예와 비교예 조성물에서 알파-리포산의 잔존량을 측정하였다. 그 결과를 다음 표 6 및 7에 나타낸다. 표 6 및 7의 값은 HPLC 분석 알파-리포산 잔존률(%)이다.In order to confirm the above results more quantitatively, the residual amount of alpha-lipoic acid in the Example and Comparative Example compositions was measured using high performance liquid chromatography (HPLC). The results are shown in the following Tables 6 and 7. The values in Tables 6 and 7 are HPLC analysis alpha-lipoic acid residual percentages.

　 실시예 1Example 1 실시예 2Example 2 실시예 3Example 3 실시예 4Example 4 실시예 5Example 5 실시예 6Example 6 실시예 7Example 7 실시예 8Example 8 실시예 9Example 9 초기값Initial value 100100 100100 100100 100100 100100 100100 100100 100100 100100 3개월후3 months later 9898 9595 9090 9494 9696 9595 9494 9393 9898 6개월후6 months later 9090 9292 8585 7070 8080 8383 8686 8989 8585

비교예 1Comparative Example 1 비교예 2Comparative Example 2 비교예 3Comparative Example 3 비교예 4Comparative Example 4 비교예 5Comparative Example 5 비교예6Comparative Example 6 초기값Initial value 100100 100100 100100 100100 100100 100100 3개월후3 months later 8080 7878 6666 8383 8282 8080 6개월후6 months later 5757 6262 5050 4545 4040 5858

위 표 6 및 7에서 보듯이, 비교예 보다 실시예에서 제조된 화장료 조성물에서 알파-리포산 함량이 더 높은 것을 알 수 있다.As shown in Tables 6 and 7, it can be seen that the alpha-lipoic acid content is higher in the cosmetic composition prepared in Example than in Comparative Example.

효과시험예 2: 경시 안정성 시험 Effect Test Example 2 Stability Test Over Time

상기의 실시예 1 내지 9 및 비교예 1 내지 6에서 제조된 화장료 조성물의 경시 안정성을 알아보기 위하여, 각각의 조성물을 400 g씩 투명 유리 용기에 담아서 실온(25 ℃), 고온(45 ℃), 일광 및 냉동-해동실(Freeze-Thaw Chamber: 45 ℃∼-10 ℃, 24 시간 주기)에 보관한 후, 칼라리메터(Model Σ80, Nippon D Enshoku)를 이용하여 측정한 결과를 다음 표 8 및 9에 나타낸다.In order to determine the stability over time of the cosmetic compositions prepared in Examples 1 to 9 and Comparative Examples 1 to 6, each composition was placed in a transparent glass container of 400 g each at room temperature (25 ° C.), high temperature (45 ° C.), After storage in daylight and freeze-thaw chamber (45 ℃ to -10 ℃, 24 hours cycle), the results measured using a colorimeter (Model Σ 80, Nippon D Enshoku) are shown in Table 8 and 9 is shown.

　 실시예 1Example 1 실시예 2Example 2 실시예 3Example 3 실시예 4Example 4 실시예 5Example 5 실시예 6Example 6 실시예 7Example 7 실시예 8Example 8 실시예 9Example 9 실온, 6개월Room temperature, 6 months Δ0 Δ0 Δ1Δ1 Δ1Δ1 Δ1Δ1 Δ1Δ1 Δ0Δ0 Δ0Δ0 Δ1Δ1 Δ1Δ1 45℃, 6개월45 ℃, 6 months Δ0Δ0 Δ1Δ1 Δ2Δ2 Δ1Δ1 Δ2Δ2 Δ1Δ1 Δ1Δ1 Δ2Δ2 Δ1Δ1 일광, 6개월Daylight, 6 months Δ2Δ2 Δ2Δ2 Δ1Δ1 Δ1Δ1 Δ2Δ2 Δ1Δ1 Δ2Δ2 Δ2Δ2 Δ2Δ2 45∼-10℃, 6개월45 ~ -10 ℃, 6 months Δ1Δ1 Δ2Δ2 Δ1Δ1 Δ2Δ2 Δ2Δ2 Δ2Δ2 Δ2Δ2 Δ2Δ2 Δ2Δ2

　 비교예 1Comparative Example 1 비교예 2Comparative Example 2 비교예 3Comparative Example 3 비교예 4Comparative Example 4 비교예 5Comparative Example 5 비교예 6Comparative Example 6 실온, 6개월Room temperature, 6 months Δ3Δ3 Δ3Δ3 Δ3Δ3 Δ3Δ3 Δ3Δ3 Δ3Δ3 45℃, 6개월45 ℃, 6 months Δ3Δ3 Δ3Δ3 Δ3Δ3 Δ3Δ3 Δ3Δ3 Δ4Δ4 일광, 6개월Daylight, 6 months Δ4Δ4 Δ4Δ4 Δ4Δ4 Δ4Δ4 Δ4Δ4 Δ4Δ4 45∼-10℃, 6개월45 ~ -10 ℃, 6 months Δ3Δ3 Δ4Δ4 Δ3Δ3 Δ4Δ4 Δ3Δ3 Δ4Δ4

* 판정기준: 변화량=컨트롤과 비교시 칼라리메터 측정치의 변화 크기.* Judgment criteria: Amount of change = the amount of change in colorimeter measurement compared to the control.

Δ0: 거의 변화 없음,Δ0: almost no change,

Δ1: 아주 약간 변함,Δ1: very slightly changed,

Δ2: 약간 변함,Δ2: slightly changed,

Δ3: 많이 변함,Δ3: change a lot,

Δ4: 아주 많이 변함.Δ4: very much changed.

위 표 8 및 9의 결과에서 보듯이, 폴리올과 비이온성 계면활성제로 알파-리포산을 안정화시킨 실시예 1 내지 9의 화장료 조성물은, 비교예 1 내지 6의 화장료 조성물에 비하여 경시 보관 안정성이 높은 것을 확인할 수 있다. 즉, 잔존한 알파-리포산의 함량을 고속액체크로마토그래피(HPLC)에 의해 정량적으로 확인한 결과, 실시예 1 내지 9의 화장료는 실온, 고온, 일광 및 냉동-해동 조건에서 경시 안정성이 거의 100 %로 안정하였지만, 비교예 1 내지 6의 경우는 안정하지 못한 것을 확인하였다.As shown in the results of Tables 8 and 9, the cosmetic compositions of Examples 1 to 9 stabilized alpha-lipoic acid with polyols and nonionic surfactants have higher storage stability over time than the cosmetic compositions of Comparative Examples 1 to 6. You can check it. That is, as a result of quantitatively confirming the content of the remaining alpha-lipoic acid by high performance liquid chromatography (HPLC), the cosmetics of Examples 1 to 9 have almost 100% stability over time at room temperature, high temperature, sunlight and freeze-thaw conditions. Although it was stable, it confirmed that it was not stable in the case of Comparative Examples 1-6.

이상에서 설명한 바와 같이, 본 발명의 화장료 조성물은 미백, 주름, 항산화, 슬리밍 등에 효과적인 알파-리포산이 조성물 내에서 변취, 변취 등 불안정화되는 것을 방지하여 안정화시킴으로써 장기간 효과를 지속시킬 수 있도록 하므로, 미 백, 주름, 항산화, 슬리밍 등의 화장료 조성물로 유용하게 사용할 수 있다.As described above, the cosmetic composition of the present invention prevents the alpha-lipoic acid, which is effective in whitening, wrinkles, antioxidants, slimming, etc. in the composition to prevent destabilization, such as odors, odors, etc., so that the long-term effect can be maintained. It can be usefully used as a cosmetic composition, such as wrinkles, antioxidants, slimming.

Claims (7)

알파-리포산을 포함하는 화장료 조성물에 있어서, 알파-리포산의 안정화제로서 조성물 총 중량에 대해서 프로필렌글리콜, 글리세린, 1,3-부틸렌글리콜, 1,3-부탄디올 및 솔비톨로 이루어지는 군으로부터 선택되는 1 종 이상의 폴리올 0.1∼30 중량%, 및 POE(폴리옥시에틸렌) 솔비탄 지방산 에스테르, POE 알킬 에테르(LA), POE 수소화 에스테르 오일, POE(10) 옥틸도데실 에테르, POE(15) 옥틸도데실 에테르, POE(20) 옥틸도데실 에테르, POE(30) 옥틸도데실 에테르, POE(15) 글리세릴 모노스테아레이트, POE(20) 글리세릴 모노스테아레이트, POE(25) 글리세릴 모노스테아레이트 및 POE(30) 글리세릴 모노스테아레이트로 이루어지는 군으로부터 선택되는 1 종 이상의 비이온성 계면활성제 0.01∼10 중량%를 포함하는 화장료 조성물.A cosmetic composition comprising alpha-lipoic acid, wherein the composition is selected from the group consisting of propylene glycol, glycerin, 1,3-butylene glycol, 1,3-butanediol, and sorbitol based on the total weight of the composition as a stabilizer of alpha-lipoic acid. 0.1-30% by weight or more of polyols, and POE (polyoxyethylene) sorbitan fatty acid ester, POE alkyl ether (LA), POE hydrogenated ester oil, POE (10) octyldodecyl ether, POE (15) octyldodecyl ether , POE (20) octyldodecyl ether, POE (30) octyldodecyl ether, POE (15) glyceryl monostearate, POE (20) glyceryl monostearate, POE (25) glyceryl monostearate and POE (30) A cosmetic composition comprising 0.01 to 10% by weight of at least one nonionic surfactant selected from the group consisting of glyceryl monostearate. 제 1 항에 있어서, 알파-리포산의 첨가량이 조성물 총 중량에 대하여 0.01∼20 중량%인 화장료 조성물. The cosmetic composition according to claim 1, wherein the amount of alpha-lipoic acid added is 0.01 to 20% by weight based on the total weight of the composition. 제 1 항에 있어서, 폴리올과 비이온성 계면활성제의 혼합량이 조성물 총 중량에 대해 0.1∼40 중량%인 화장료 조성물.The cosmetic composition according to claim 1, wherein the mixing amount of the polyol and the nonionic surfactant is 0.1 to 40% by weight based on the total weight of the composition. 제 1 항에 있어서, 폴리올과 비이온성 계면활성제의 혼합비율이 1∼7:1∼5인 것을 특징으로 하는 화장료 조성물.The cosmetic composition according to claim 1, wherein the mixing ratio of the polyol and the nonionic surfactant is from 1 to 7: 1 to 5. 삭제delete 삭제delete 제 1 항에 있어서, 스킨, 로션, 크림, 파운데이션 또는 에센스인 화장료 조성물.The cosmetic composition according to claim 1, which is a skin, lotion, cream, foundation or essence.
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Cited By (2)

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Publication number Priority date Publication date Assignee Title
KR20170016664A (en) 2015-08-04 2017-02-14 고려대학교 산학협력단 Method for manufacturing fatty acid-starch nano complex and fatty acid-starch nanocomplex prepared by the method
CN114010522A (en) * 2021-12-22 2022-02-08 郑州大学 Lipoic acid mixed micelle and preparation method and application thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998002438A1 (en) 1996-07-13 1998-01-22 Glaxo Group Limited Bicyclic heteroaromatic compounds as protein tyrosine kinase inhibitors
WO2001007432A2 (en) 1999-07-23 2001-02-01 Smithkline Beecham P.L.C. Aminopiperidine derivatives as antibacterials

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998002438A1 (en) 1996-07-13 1998-01-22 Glaxo Group Limited Bicyclic heteroaromatic compounds as protein tyrosine kinase inhibitors
WO2001007432A2 (en) 1999-07-23 2001-02-01 Smithkline Beecham P.L.C. Aminopiperidine derivatives as antibacterials

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170016664A (en) 2015-08-04 2017-02-14 고려대학교 산학협력단 Method for manufacturing fatty acid-starch nano complex and fatty acid-starch nanocomplex prepared by the method
CN114010522A (en) * 2021-12-22 2022-02-08 郑州大学 Lipoic acid mixed micelle and preparation method and application thereof
CN114010522B (en) * 2021-12-22 2023-10-13 郑州大学 Lipoic acid mixed micelle and preparation method and application thereof

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