KR102054417B1 - Cosmetic composition materials having activity for ultraviolet protection - Google Patents
Cosmetic composition materials having activity for ultraviolet protection Download PDFInfo
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- KR102054417B1 KR102054417B1 KR1020180065142A KR20180065142A KR102054417B1 KR 102054417 B1 KR102054417 B1 KR 102054417B1 KR 1020180065142 A KR1020180065142 A KR 1020180065142A KR 20180065142 A KR20180065142 A KR 20180065142A KR 102054417 B1 KR102054417 B1 KR 102054417B1
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
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- A61K8/00—Cosmetics or similar toiletry preparations
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- 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
- A61K8/35—Ketones, e.g. benzophenone
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- A61K8/00—Cosmetics or similar toiletry preparations
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- 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
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
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Abstract
Description
본 발명은 자외선 차단효과를 나타내는 성분을 봉입하여 그의 광안정성, 수 분산성 및 자외선차단 효능을 증가시킬 수 있는 제제 및 그의 기본 구성물질의 개발에 관한 것이다.The present invention relates to the development of a formulation and its basic components capable of encapsulating a component exhibiting a sunscreen effect to increase its photostability, water dispersibility and sunscreen efficacy.
화장품이나 의약의 원료 물질들 중에는 낮은 광안정성과 수분산성 문제가 되는 물질들이 다수 존재한다. 지표면에 도달하는 자외선(UV)은 UVA (320~400nm)와 UVB (290~320nm)가 주를 이루며 피부화상, 피부노화, 또한 멜라닌 생성을 유도하여 피부를 검게하므로 자외선 차단제를 사용하여 피부를 보호한다. 자외선 차단제로 많이 사용되는 아보벤존(Avobenzone)은 360nm에서 최대흡광을 가지는 UVA 자외선 차단제에 일반적으로 많이 사용되는 백색의 파우더로 Butyl Methoxydibenzoylmethane로 ICID에 등록되어 있으며 상품명으로 Parsol 1789, Milestab 1789, Eusolex 9020, Escalol 517, Neo Heliopan 357 등으로 불리는데, 광안정성이 낮고 물에 잘 분산되지 않는다. 아보벤존은 석출 및 티타늄 디옥사이드에 흡착, 안정화를 위해 옥토크릴렌과 함께 사용해야 하며, UV 노출시 급격히 분해되어 아보벤존은 Enol form을 거처 Rotamer로 변형되어 UVA 차단제로써 기능을 상실하게 된다(비특허문헌 1, 2).Among the raw materials of cosmetics and pharmaceuticals, there are a number of substances that have low light stability and water dispersibility problems. UV rays reaching the surface are mainly UVA (320 ~ 400nm) and UVB (290 ~ 320nm) and induce skin burn, skin aging, and melanin production to blacken the skin, thus protecting the skin with sunscreen. do. Avobenzone, a commonly used sunscreen, is a white powder commonly used for UVA sunscreens with a maximum absorption at 360 nm. It is registered with ICID as Butyl Methoxydibenzoylmethane, under the trade names Parsol 1789, Milestab 1789, Eusolex 9020, It is called Escalol 517, Neo Heliopan 357, etc. It has low light stability and does not disperse well in water. Avobenzone must be used with octocrylene for adsorption and stabilization on precipitation and titanium dioxide, and rapidly decomposes upon UV exposure, resulting in the transformation of avobenzone to rotamer via the enol form and losing its function as a UVA blocker. 1, 2).
활성물질의 광안정성을 높이고 수용액 중에서의 용해도를 증강시키는 방법으로 합성 고분자소재에 관한 연구가 진행되고 있다. 관련 특허로써 대한민국특허 10-1679118호의 폴리감마글루타민산 유도체에 비타민을 함유시킨 제제에 관한 특허는 이러한 합성고분자 소재를 공기 중에 쉽게 산화되는 비타민을 봉입시 산화적 안정성이 증가됨을 제시하고 있으나 특허권리범위를 비타민을 함유하는 유도체에 한정하고 있으며, 햇빛이나 자외선에 노출시 광안정성을 높일 수 있는 제제에 대한 근거나 내용을 제시하고 있지 않다. Research into synthetic polymer materials has been conducted as a method of increasing the light stability of active materials and enhancing their solubility in aqueous solutions. As a related patent, a patent for a formulation containing vitamins in polygamma glutamic acid derivatives of Korean Patent No. 10-1679118 suggests that the oxidative stability is increased when the vitamin is easily oxidized in the air. It is limited to derivatives containing vitamins, and it does not provide any evidence or content on preparations that can enhance photostability when exposed to sunlight or ultraviolet light.
본 발명은 자외선 차단효과를 나타내는 성분을 봉입하여 그의 광안정성, 수분산성 및 자외선차단 효능을 증가시킬 수 있는 제제 개발과 그것을 포함하는 화장료 조성물 개발을 목적으로 한다.An object of the present invention is to encapsulate a component that exhibits a sunscreen effect, and to develop a formulation capable of increasing its photostability, water dispersibility, and sunscreen efficacy, and a cosmetic composition including the same.
하기와 같은 본 발명의 구체적인 양태를 통하여 상기의 목적을 달성할 수 있었다:Through the following specific aspects of the present invention it was possible to achieve the above object:
(1) 폴리감마글루탐산의 카르복시기에 페닐알라닌 유도체의 아민기와 결합되어 있는 폴리감마글루타민산 유도체;(1) a polygamma glutamic acid derivative bonded to an amine group of a phenylalanine derivative in a carboxyl group of polygamma glutamic acid;
(2) 친수성기와 친유성기를 함께 가지는 기본물질로서 상기 (1)의 폴리감마(2) The polygamma of the above (1) as a base material having both a hydrophilic group and a lipophilic group
글루타민산 유도체를 포함하는 입자;Particles comprising glutamic acid derivatives;
(3) 상기 (2)에 있어서, 입자의 크기가 20 내지 1,000 nm인 입자;(3) The particle according to the above (2), wherein the particle has a size of 20 to 1,000 nm;
(4) 상기 (2) 또는 (3)에 있어서, 아보벤존 또는 이와 유사한 자외선 차단기능을 하는 물질이 봉입된 제제;(4) The preparation according to the above (2) or (3), wherein an agent containing avobenzone or similar ultraviolet blocking function is encapsulated;
(5) 상기 (4)의 제제를 포함하는 화장품 조성물(5) Cosmetic composition containing the formulation of said (4)
본 발명의 폴리감마글루타민산 유도체에 자외선차단기능을 하는 물질을 봉입시킨 제제는 화장품 혹은 의약에 있어서 효율적인 전달시스템으로 적용 가능하며 기존의 자외선 차단기능을 하는 물질들이 갖는 문제점인 광안정성이 낮고 물에 녹지 않고 잘 분산되지 않는 특성을 개선하여 광안정성 및 수분산성을 높임으로써 자외선 차단효능을 증가시킬 수 있다. The formulation containing the UV-blocking substance in the poly-gamma glutamic acid derivative of the present invention is applicable to an efficient delivery system in cosmetics or medicines, and has a low light stability, which is a problem of conventional UV-blocking substances, and is insoluble in water. It is possible to increase the UV blocking effect by improving the light stability and water dispersion by improving the properties that are not well dispersed.
이러한 본 발명의 폴리감마글루타민산 유도체에 자외선차단기능을 하는 물질을 봉입시킨 제제는 외부의 환경으로부터 활성물질의 노출을 차단함으로써 자외선에 불안정한 활성물질의 광안정성을 높여 효율적으로 화장품 혹은 의약으로의 적용을 가능케 한다.Such a formulation in which the polygamma glutamic acid derivative of the present invention is encapsulated with a substance having a sunscreen function increases the photostability of an active substance which is unstable to ultraviolet rays by blocking the exposure of the active substance from an external environment, thereby effectively applying it to cosmetics or medicine. Make it possible.
또한 본 발명의 폴리감마글루타민산 유도체에 자외선차단기능을 하는 물질을 봉입시킨 제제의 내부는 소수성이고 외부는 친수성이기 때문에 봉입된 활성물질은 입자 상태로서 수 중에 용이하게 안정적으로 분산되므로 난용성 활성물질의 화장품 혹은 의약으로의 적용을 가능케하며 나아가 효율적인 적용을 제공한다.In addition, since the inside of the preparation encapsulating a substance which acts as a sunscreen in the polygamma glutamic acid derivative of the present invention is hydrophobic and the outside is hydrophilic, the enclosed active material is dispersed in water easily and stably in the form of particles. It can be applied to cosmetics or medicine and furthermore, to provide efficient application.
도 1은 폴리감마글루타민산 유도체에 아보벤존을 봉입시킨 실시예(3)-1 제제(APGA-Avobenzone)의 입자도 시험결과이며,
도2는 폴리감마글루타민산 유도체에 아보벤존을 봉입시킨 제제(APGA-Avobenzone)의 실시예(3)-2의 합성수율 및 봉입율 조사결과이며,
도3은 실시예(4)의 아보벤존을 UVA 구간 및 360nm에서의 광안정성 조사시험결과이며,
도4는 실시예(4)의 폴리감마글루타민산 유도체에 아보벤존을 봉입시킨 제제(APGA-Avobenzone)를 UVA 구간 및 360nm에서의 광안정성 조사시험결과이며,
도5는 APGA-Avobenzone 제제 함유 화장료 조성물의 실시예(5)-1 가혹조건에서 pH 안정성 시험결과이며,
도6는 APGA-Avobenzone 제제 함유 화장료 조성물의 실시예(5)-1 가혹조건에서 비중 안정성 시험결과이며,
도7는 APGA-Avobenzone 제제 함유 화장료 조성물의 실시예(5)-1 가혹조건에서 점도 안정성 시험결과이다.1 is a test result of the particles of the Example (3) -1 formulation (APGA-Avobenzone) in which avobenzone is encapsulated in a polygamma glutamic acid derivative.
FIG. 2 shows the results of investigation of the synthesis yield and the encapsulation rate of Example (3) -2 of the preparation (APGA-Avobenzone) in which avobenzone was encapsulated in a polygamma glutamic acid derivative.
3 is a light stability test results of the avobenzone of Example (4) in the UVA section and 360nm,
FIG. 4 is a light stability test result of UVA section and 360 nm of the formulation (APGA-Avobenzone) in which avobenzone is encapsulated in the polygamma glutamic acid derivative of Example (4).
5 is a pH stability test result of Example (5) -1 harsh conditions of the APGA-Avobenzone formulation-containing cosmetic composition,
6 is a specific gravity stability test result of Example (5) -1 harsh conditions of the cosmetic composition containing APGA-Avobenzone formulations,
7 is a viscosity stability test results of Example (5) -1 harsh conditions of the cosmetic composition containing APGA-Avobenzone formulations.
본 발명은 자외선 차단효과를 나타내는 성분을 봉입하여 광안정성, 수 분산성 및 자외선차단 효능을 크게 증가시킬 수 있는 제제 및 그의 기본 구성물질의 개발에 관한 것이다.The present invention relates to the development of a formulation and its basic constituents that can significantly increase the light stability, water dispersibility and sunscreen efficacy by encapsulating components exhibiting a sunscreen effect.
본 발명자들은 폴리감마글루탐산 유도체를 이용하여 자외선차단기능을 나타내는 아보벤존을 봉입하여 광안정성과 분산성을 높여줌으로써 자외선차단 효능을 크게 증가시킬 수 있는 제제의 제조에 성공하였다. 본 자외선차단 효능을 나타내는 제제는 다양한 화장품제형에 첨가하여 사용할 수 있다. The present inventors have succeeded in the preparation of a formulation that can significantly increase the sunscreen efficacy by encapsulating avobenzone, which exhibits a sunscreen function, using polygammaglutamic acid derivatives to increase light stability and dispersibility. Formulations showing the present sunscreen efficacy can be used in addition to various cosmetic formulations.
페닐알라닌의 아민기 (-NH2)를 폴리감마글루탐산의 카르복실기 (-COOH)에 선택적으로 결합시키기 위해서는 페닐알라닌의 카르복실기를 차폐한 형태의 페닐알라닌 유도체를 이용하는 것이 바람직하다. 페닐알라닌 유도체의 예로서는 페닐알라닌 메틸 에스터, 페닐알라닌 에틸 에스터, 페닐알라닌 프로필 에스터, 페닐알라닌부틸 에스터, 페닐알라닌 펜틸 에스터, 페닐알라닌 헥실 에스터 및 페닐알라닌 벤질 에스터 등이 있다. 이러한 페닐알라닌 유도체를 이용하여 페닐알라닌 카르복실기를 차폐한 다음 페닐알라닌의 아민기를 폴리감마글루탐산의 카르복실기와 결합시키는 것이 효율적이다. 바람직하게는 상기 페닐알라닌 유도체로서 페닐알라닌 에틸In order to selectively bind the amine group (-NH2) of phenylalanine to the carboxyl group (-COOH) of polygamma glutamic acid, it is preferable to use the phenylalanine derivative of the form which masked the carboxyl group of phenylalanine. Examples of phenylalanine derivatives include phenylalanine methyl ester, phenylalanine ethyl ester, phenylalanine propyl ester, phenylalanine butyl ester, phenylalanine pentyl ester, phenylalanine hexyl ester and phenylalanine benzyl ester. It is effective to mask the phenylalanine carboxyl group using such a phenylalanine derivative and then combine the amine group of phenylalanine with the carboxyl group of polygammaglutamic acid. Preferably phenylalanine ethyl as the phenylalanine derivative
에스터를 이용할 수 있다.Ester can be used.
본 발명의 폴리감마글루탐산 유도체는 중심축 (backbone)을 The polygamma glutamic acid derivatives of the present invention have a backbone.
이루는 글루탐산들이 친수성 부분을 구성하고 치환되어 들어간 페닐알라닌 부분이 소수성 부분을 구성한다. 즉 본 발명의 폴리감마글루탐산 유도체는 양친매성을 갖는다. 따라서 본 발명의 폴리감마글루탐산 유도체는 수 중에 분산시켰을 때 친수성부분이 밖을 향하고 소수성 부분이 구의 중심쪽으로 모여 미셀을 용이하게 형성하게 된다. 이때 지용성 혹은 난용성 활성물질은 입자의 내부 소수성 부분의 안쪽에 자연스럽게 위치하게 되므로 자외선차단 활성물질을 입자 내에 용이하게 봉입할 수 있는 것이다. 입자 내에 봉입되지 않은 상태에서 자외선차단제가 물에 접하게 되면 바로 석출되거나 오일인 경우 물 표면에 떠올라 바로 층분리가 일어나겠지만, 입자 내에 봉입된 지용성 혹은 난용성 활성물질은 수 중에 분산되어도 입자 표면에는 글루탐산들에 의한 친수성 부분이 차지하고 있으므로 입자 내에 봉입된 자외선차단 기능의 물질은 입자 외부 환경에 노출되어 있지않고 입자 구성물질에 의하여 보호되어 있기 때문에 자외선 조사환경에 그대로 노출된 상태에 비하여 안정성을 월등하게 보장받으며 본래 자외선 차단제로써의 기능을 오랫동안 유지할 수 있다. 또한 안정적으로 분산되어 있을 수 있다. The resulting glutamic acids make up the hydrophilic moiety and the substituted phenylalanine moiety makes up the hydrophobic moiety. That is, the polygamma glutamic acid derivative of the present invention has amphipathicity. Therefore, when the polygamma glutamic acid derivative of the present invention is dispersed in water, the hydrophilic portion is directed outward and the hydrophobic portion is collected toward the center of the sphere to easily form micelles. At this time, since the fat-soluble or poorly soluble active material is naturally located inside the hydrophobic portion of the particle, the sunscreen active material can be easily encapsulated in the particle. If the sunscreen comes into contact with water without being encapsulated within the particles, it will precipitate immediately or float on the surface of the oil if it is oil. However, the fat-soluble or poorly soluble active substance encapsulated in the particles may be dispersed in water, As the hydrophilic part is occupied by the field, the UV-blocking material encapsulated in the particle is not exposed to the external environment of the particle and is protected by the particle constituents, so it is more stable than the state exposed to the UV irradiation environment. It can keep its function as a sunscreen for a long time. It may also be stably dispersed.
본 발명의 자외선차단 활성물질을 봉입시킨 제제 입자를 안정적으로 형성하기만 하면 그 크기에 특별한 한정은 없다. 다만, 제제 입자의 크기가 20 내지 1000 nm인 것이 특히 바람직하다.There is no particular limitation on the size as long as it stably forms the preparation particles containing the sunscreen active substance of the present invention. However, it is particularly preferable that the size of the formulation particles is 20 to 1000 nm.
이하 실시예 등을 통하여 본 발명의 자외선차단 활성물질을 봉입시킨 제제를 기반으로 하는 아보벤존 함유 제제의 제조에 관하여 구체적인 예를 기술하지만 본 발명의 내용이 이에 한정되는 것을 아니다.Hereinafter, specific examples of the preparation of avobenzone-containing preparations based on the preparations containing the sunscreen active substance of the present invention will be described through Examples, but the present invention is not limited thereto.
실시예 (1). 폴리감마글루탐산 유도체의 제조Example (1). Preparation of Polygamma Glutamic Acid Derivatives
250ml 둥근 플라스크에 분자량 50K의 폴리감마글루탐산 1g을 탄산수소나트륨 0.3M 농도 40ml의 용액에 녹인다. 페닐알라닌과의 커플링을 위해 분자량 50K의 폴리감마글루탐산에 1:387의 당량 비율로 에틸(디메틸아미노프로필)카보디이미드[ethyl(dimethylaminopropyl) carbodiimide: EDC]를 1.5g을 탄산수소나트륨 0.3M농도 5ml에 용해시켜 250ml 둥근 플라스크에 첨가하여 0℃ 환경에서 30분 동안 반응시킨다. 그 후 페닐알라닌 에틸 에스터를 1 : 387 당량 비율로 1.8g을 15ml 코니칼 튜브 (conical tube)에 담은 후 가루채로 250ml 둥근 플라스크에 단계적으로 녹이면서 첨가한 후 탄산수소나트튬 0.3M 농도 5ml의 용액으로 워싱 후 250ml 둥근플라스크에 첨가하여 12시간 동안 반응 시킨다.In a 250 ml round flask, 1 g of polygamma glutamic acid having a molecular weight of 50 K is dissolved in a solution of 40 ml of 0.3 M sodium hydrogen carbonate. For coupling with phenylalanine, 1.5 g of ethyl (dimethylaminopropyl) carbodiimide (EDC) was added to polygamma glutamic acid having a molecular weight of 50 K at an equivalent ratio of 1: 387, and sodium hydrogencarbonate 0.3
그 후, MWCO (molcular weight cut off) 3,500의 여과막을 이용하여 하루 동안은 삼차 증류수상에서, 다음 이틀은 메탄올 (MeOH)상에서 반응하지 못한 페닐알라닌, 에틸(디메틸아미노프로필)카보디이미드(EDC) 그리고 탄산수소나트륨을 여과시킨다. 페닐알라닌이 결합된 폴리감마글루탐산을 여과막에서 250ml 둥근 플라스크로 다시 옮겨 여과막으로 인한 용매치환의 결과인 메탄올(MeOH)을 감압장치를 이용하여 제거하여 본 발명의 폴리감마글루탐산 유도체를 수득하였다.Subsequently, phenylalanine, ethyl (dimethylaminopropyl) carbodiimide (EDC) and carbonic acid were not reacted in tertiary distilled water for one day using a molecular weight cut off (MWCO) 3,500 filter membrane for one day and in methanol (MeOH) for two days. Sodium hydrogen is filtered. Phenylalanine-bound polygamma glutamic acid was transferred from the filtration membrane to a 250 ml round flask to remove methanol (MeOH), which is a result of solvent replacement due to the filtration membrane, using a pressure reduction apparatus to obtain a polygamma glutamic acid derivative of the present invention.
실시예 (2). 폴리감마글루탐산 유도체 입자(APGA)의 제조Example (2). Preparation of Polygamma Glutamic Acid Derivative Particles (APGA)
상기 실시예 (1)에서 제조한 폴리감마글루탐산 유도체를 모두 삼차 증류수Tertiary distilled water with all polygamma glutamic acid derivatives prepared in Example (1)
50ml에 분산시킨 후 동결건조 하여 하얀색 파우더로서 본 발명의 입자 (APGA) 1 g을 수득하였다.It was dispersed in 50ml and lyophilized to obtain 1 g of the particles (APGA) of the present invention as a white powder.
실시예 (3) 아보벤존이 봉입된 제제(APGA-Avobenzone) 제조Example (3) Preparation of Avobenzone Encapsulated Formulation (APGA-Avobenzone)
실시예 (2)에서 제조한 APGA 1 g과 봉입할 자외단 기능 활성원료 아보벤존(Aobenzone)을 봉입수율에 따른 적량을 넣고 Chloroform와 MeOH 혼합액에 넣고 sonication하여 잘 분산시킨다. 여기에 TDW를 넣고 이를 seperation funnel에 옮기고 Methylene chloride를 넣고 흔들어서 washing후 층분리가 일어나면 아래 Methylene chloride 층을 버리는 Washig 과정을 2번 반복. TDW층을 동결건조 하여 자외선 차단 기능 활성 원료 아보벤존이 봉입된 APGA-Avobenzone powder를 얻었다.1 g of APGA prepared in Example (2) and the ultraviolet-functional functional ingredient Avobenzone to be encapsulated are added in appropriate amounts according to the encapsulation yield, sonicated and dispersed in Chloroform and MeOH mixed solution. Put TDW here, transfer it to seperation funnel, add Methylene chloride, shake, wash, and then separate the layers of Methylene chloride after washing. Repeat the Washig process twice. The TDW layer was lyophilized to obtain APGA-Avobenzone powder encapsulated with UV-protective active material Avobenzone.
실험예 1. 아보벤존이 봉입된 제제(APGA-Avobenzone)의 크기 측정Experimental Example 1. Measurement of the size of the preparation (APGA-Avobenzone) containing avobenzone
실시예 (3)의 APGA-Avobenzone을 각각 삼차증류수에 분산시키고 이렇게 형성된 제제 입자 현탁액에 대하여 입자크기를 측정을 위해 한국화학융합시험연구원에 분석의뢰하였다. 공인성적서 결과에 따라 비타민 E 아세트산이 봉입된 나노 입자는 균일한 크기를 가지고 있음을 확인할 수 있었으며 평균 454.6nm의 입자크기를 나타내었다(도 1).The APGA-Avobenzone of Example (3) was dispersed in tertiary distilled water, respectively, and was analyzed by the Korea Institute of Chemical Fusion Testing to determine the particle size of the prepared particle suspension. According to the results of the official report, it was confirmed that the nanoparticles encapsulated with vitamin E acetic acid had a uniform size and showed an average particle size of 454.6 nm (FIG. 1).
실험예 2. APGA-Avobenzone 제제의 합성수율 및 봉입율 Experimental Example 2. Synthetic yield and encapsulation rate of APGA-Avobenzone preparation
APGA 0.1g에 각각 아보벤존 0.001g, 0.005g, 0.01g, 0.02g, 0.05g을 가하고 봉입후 동결건조하여 분말형태로 얻었다. 각 동결건조 분말 10 mg을 methanol : chloroform = 1 : 1용액 10 ml에 녹여서 360nm에서 흡광도를 측정하여 아보벤존의 양을 검량선에 대입하여 봉입된 아보벤존 함량을 계산하였다. 그 결과 APGA 0.1g에 아보벤존 0.005g 비율로 합성시 96.2%로 합성수율이 가장높게 나타났고(도 2a), 봉입율은 APGA 0.1g에 아보벤존 0.02g 비율로 합성시 17.5%로 봉입율이 가장높게 나타났다(도 2b).Avobenzone 0.001g, 0.005g, 0.01g, 0.02g, 0.05g was added to 0.1 g of APGA, and then lyophilized after encapsulation to obtain a powder form. 10 mg of each lyophilized powder was dissolved in 10 ml of methanol: chloroform = 1: 1 solution, and the absorbance was measured at 360 nm. Subsequently, the amount of enclosed avobenzone was calculated by substituting the amount of avobenzone into the calibration curve. As a result, the synthesis yield was 96.2% when the compound was synthesized at 0.15% of avobenzone at 0.1g of APGA (Fig. 2a), and the encapsulation rate was 17.5% when synthesized at 0.02g of avobenzone at 0.1g of APGA. It was highest (Figure 2b).
실시예 (4) APGA-Avobenzone 제제의 광안정성 조사Example (4) Photostability Study of APGA-Avobenzone Formulations
UBA광원에 sonication하여 분산한 아보벤존과 상기 실시예 (3)의 APGA-Avobenzone제제를 500mW/cm2의 에너지에 0, 30, 60, 90, 120분을 노출하고 그 변화량을 측정하였다. 아보벤존의 경우 UBA에 노출된 시간이 경과될수록 흡광도가 급격히 감소함을 볼 수 있으며, 2시간이 경과하자 초기량의 절반만 남았다(도 3). 반면 APGA-Avobenzone제제는 2시간 후에도 초기량과 큰 변화 없이 안정적인 결과를 나타냈다(도 4). The avobenzone dispersed by sonication in the UBA light source and the APGA-Avobenzone preparation of Example (3) were exposed to energy of 500 mW /
실시예 (5) APGA-Avobenzone 제제를 함유하는 화장료 조성물 제조Example (5) Preparation of cosmetic composition containing APGA-Avobenzone preparation
실시예 (3)의 APGA-Avobenzone 제제를 0.5%로 하고 정제수, 징크옥사이드, 이소아밀라우레이트, 티타늄디옥사이드, 에칠헥실메톡시신나메이트, 글리세린, 에칠헥실살리실레이트, 사이클로펜타실록산, 세틸피이지/피피지-10/1디메치콘, 나이아신아마이드, 소듐클로라이드, 다이메치콘, 알루미늄하이드록사이드, 스테아릭애씨드, 다이메치콘/메치콘코폴리머, 디스테아디모늄헥토라이트, 소르비탄세스퀴올리에이트, 부틸렌글라이콜,하이드록시아세토페논, 1,2-헥산디올, 아데노신, 라벤더 오렌지껍질오일 등을 적량으로 하는 화장품조성물을 제조하였다.The APGA-Avobenzone preparation of Example (3) was 0.5%, and purified water, zinc oxide, isoamylaurate, titanium dioxide, ethexyl methoxycinnamate, glycerin, ethhexyl salicylate, cyclopentasiloxane, and cetylpage / Fiji-10 / 1 dimethicone, niacinamide, sodium chloride, dimethicone, aluminum hydroxide, stearic acid, dimethicone / methicone copolymer, disteadimonium hectorite, sorbitan sesquioleate , Butylene glycol, hydroxy acetophenone, 1,2- hexanediol, adenosine, lavender orange peel oil and the like to prepare a cosmetic composition.
실험예 1. APGA-Avobenzone 제제를 함유하는 화장료 조성물의 안정성 조사Experimental Example 1. Investigation of stability of cosmetic composition containing APGA-Avobenzone preparation
실시예(5)에서 제조한 발명의 APGA-Avobenzone 제제를 포함하는 화장료 조성물을 가혹조건 안정성 시험을 수행하였다. 시험법은 가이드라인에 따라 50℃ -> 상온 -> -20℃를 반복하여 보관하며 2주간 pH, 비중, 점도변화를 조사한 결과 아래와 같았다. 나타난 바와같이 pH, 비중, 점도상에 큰 변화가 나타나지 않는 안정적인 결과를 나타냄을 확인하였다(도5, 도6, 도7).The cosmetic composition containing the APGA-Avobenzone preparation of the invention prepared in Example (5) was subjected to harsh condition stability test. The test method was repeatedly stored at 50 ℃-> room temperature-> -20 ℃ according to the guidelines, and the changes in pH, specific gravity, and viscosity for two weeks were as follows. As shown, it was confirmed that the result shows a stable result that does not show a large change in pH, specific gravity, viscosity (Fig. 5, Fig. 6, Fig. 7).
실시예 (6) APGA-Avobenzone 제제를 함유하는 화장료 조성물의 자외선차단 효능 인체적용시험Example (6) Human application test of sunscreen efficacy of cosmetic composition containing APGA-Avobenzone preparation
APGA-Avobenzone 제제를 함유하는 화장료 조성물의 자외선차단 효능 인체적용시험은 전문임상시험기관인 한국화학융합시험연구원에서 다음과 같은 방법으로 진행하였다. 성인남녀 10명이상을 대상으로 광원으로 Multi-port solar stimulator 601-300W, 시료량은 2mg/제곱센티미터, 도포면적은 35제곱센티미터, 도포후 대기시간은 15분, 최소홍반량판정시간은 16~24시간, 시험결과계산은 SPF 평균값 및 표준편차를 구하였고 정확성 검증은 95% 신뢰구간 평균값의 20%내외이내임을 확인하였다. 표준시료는 시료의 예상지수에 따라 높은 자외선차단지수의 표준시료를 사용하였으며 기능성화장품 심사에 관한 규정(식품의약품안전처 고시 제 2017-42호)의 처방에 따라 제조하였다. 그 결과 시험시료인 APGA-Avobenzone 제제를 함유하는 화장료 조성물의 자외선차단지수는 SPF 52에 해당하는 것으로 판단되며 시험이 진행되는 동안 모든 시험대상자에게서 특별히 피부반응은 나타나지 않았다(표1).The sunscreen efficacy of the cosmetic composition containing APGA-Avobenzone preparations was tested by the Korea Institute of Chemical Convergence Testing, a professional clinical laboratory. Multi-port solar stimulator 601-300W as a light source for more than 10 adult men and women, sample volume 2mg / square centimeter,
Claims (2)
광안정성이 증가된 자외선 차단용 화장료 조성물.
Including the preparation which the avobenzone which shows the ultraviolet-ray blocking effect is enclosed in the nanoparticle containing the polygamma glutamic acid derivative which the amine group of the phenylalanine derivative couple | bonded with the carboxy group of poly gamma glutamic acid,
UV protection cosmetic composition with increased light stability.
The cosmetic composition according to claim 1, wherein the formulation has a particle size of 20 to 1000 nm.
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