KR20060102175A - Cosmetic composition for whitening of the skin having silanoyl oxymethyl-methyl imidazole derivatives - Google Patents

Cosmetic composition for whitening of the skin having silanoyl oxymethyl-methyl imidazole derivatives Download PDF

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KR20060102175A
KR20060102175A KR1020050024122A KR20050024122A KR20060102175A KR 20060102175 A KR20060102175 A KR 20060102175A KR 1020050024122 A KR1020050024122 A KR 1020050024122A KR 20050024122 A KR20050024122 A KR 20050024122A KR 20060102175 A KR20060102175 A KR 20060102175A
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methyl
imidazole
oxymethyl
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김호정
장윤희
김원찬
강상진
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주식회사 엘지생활건강
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    • CCHEMISTRY; METALLURGY
    • C02TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02FTREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00Treatment of water, waste water, or sewage
    • C02F1/001Processes for the treatment of water whereby the filtration technique is of importance
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D39/00Filtering material for liquid or gaseous fluids
    • B01D39/14Other self-supporting filtering material ; Other filtering material
    • B01D39/20Other self-supporting filtering material ; Other filtering material of inorganic material, e.g. asbestos paper, metallic filtering material of non-woven wires
    • B01D39/2027Metallic material
    • CCHEMISTRY; METALLURGY
    • C02TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02FTREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2303/00Specific treatment goals
    • C02F2303/04Disinfection
    • CCHEMISTRY; METALLURGY
    • C02TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02FTREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2307/00Location of water treatment or water treatment device
    • C02F2307/06Mounted on or being part of a faucet, shower handle or showerhead

Abstract

본 발명은 피부 미백용 화장료 조성물에 관한 것으로서, 더욱 상세하게는 하기 화학식 1로 표시되는 실라노일 옥시메틸-메틸 이미다졸 유도체를 유효성분으로 포함하는 멜라닌 생성 억제용 조성물 및 피부 미백용 화장료 조성물에 관한 것이다.The present invention relates to a cosmetic composition for skin whitening, and more particularly, to a composition for inhibiting melanin production and a cosmetic composition for skin whitening comprising a silanoyl oxymethyl-methyl imidazole derivative represented by the following Formula 1 as an active ingredient: will be.

본 발명의 피부 미백용 화장료 조성물은 피부의 멜라닌 생성을 억제함으로써, 기미나 주근깨 개선 및 피부 미백 효과가 매우 우수하다. The cosmetic composition for skin whitening of the present invention suppresses melanin production of the skin, and is very excellent in improving blemishes and freckles and skin whitening effect.

[화학식 1][Formula 1]

Figure 112005015244690-PAT00001
Figure 112005015244690-PAT00001

(상기 식에서 R1, R2 및 R3는 명세서 내에서 정의한 바와 같다.)(Wherein R 1 , R 2 and R 3 are as defined in the specification).

멜라닌, 피부 미백, 화장료 Melanin, skin whitening, cosmetics

Description

실라노일 옥시메틸-메틸 이미다졸 유도체를 포함하는 피부 미백용 화장료 조성물{Cosmetic Composition for Whitening of the Skin Having Silanoyl oxymethyl-methyl imidazole derivatives}Cosmetic composition for whitening of skin comprising silanoyl oxymethyl-methyl imidazole derivatives

[산업상 이용분야][Industrial use]

본 발명은 피부의 멜라닌 생성을 억제함으로써, 기미나 주근깨 개선 및 피부 미백 효과가 매우 우수한 멜라닌 생성 억제용 조성물 및 피부 미백용 화장료 조성물에 관한 것이다.The present invention relates to a composition for inhibiting melanin production and a cosmetic composition for skin whitening, which are excellent in improving skin and freckles and skin whitening effect by inhibiting melanin production of the skin.

[종래기술][Private Technology]

희고 고운 피부를 갖고자 하는 것은 모든 사람의 한결같은 소망이다. 사람의 피부색은 피부내 멜라닌(melanin)의 농도와 분포에 따라 유전적으로 결정되나, 태양 자외선이나 피로, 스트레스 등의 환경적 또는 생리적 조건에 의해서도 영향을 받는다. 멜라닌은 아미노산의 일종인 티로신(tyrosine)에 티로시나제(tyrosinase)라는 효소가 작용하여 도파(DOPA), 도파퀴논(dopaquinone)으로 바뀐 후 비효소적인 산화 반응을 거쳐 만들어 진다. 그러나 멜라닌이 만들어지는 경로는 알려져 있으나, 티로시나제가 작용하는 이전 단계인 멜라닌 합성을 유도하는 메카니즘 (mechanism)이 무엇인지에 대해서는 아직도 자세히 밝혀지지 않고 있다.It is everyone's constant desire to have white, fair skin. Human skin color is genetically determined by the concentration and distribution of melanin in the skin, but is also influenced by environmental or physiological conditions such as solar ultraviolet rays, fatigue and stress. Melanin is produced through a non-enzymatic oxidation reaction after tyrosine, an amino acid, acts as an enzyme called tyrosinase, transforming it into dopa and dopaquinone. However, although the pathway by which melanin is made is known, it is still not clear what mechanism is responsible for inducing melanin synthesis, the previous step in which tyrosinase works.

이에 종래에는 하이드로퀴논(hydroquinone)이나 아스콜빈산(ascorbic acid), 코지산(kojic acid), 글루타치온(glutathione)과 같이 티로시나제 저해 활성을 갖는 물질을 연고나 화장료에 배합하여, 피부 미백이나 기미, 주근깨 개선의 목적에 사용하여 왔으나, 피부에 자극을 유발하거나 제품 안정성이 좋지 못하여 사용이 제한되고, 또한 그 효과도 미약한 단점이 있었다.    Therefore, conventionally, a substance having a tyrosinase inhibitory activity such as hydroquinone, ascorbic acid, kojic acid, glutathione, and the like is added to the ointment or cosmetics to make skin whitening, blemishes, and freckles. Although it has been used for the purpose of improvement, the use is limited because it causes skin irritation or poor product stability, and also has a weak effect.

따라서 본 발명자들은 멜라닌 합성 유도 자체를 억제하는 물질까지 스크리닝(screening)할 수 있는 쥐의 멜라노마 세포(B16 mouse melanoma cell)를 이용하여 새로운 미백제를 개발하고자, 연구를 거듭한 결과, 실라노일 옥시메틸-메틸 이미다졸 유도체가 매우 강력한 멜라닌 생성 억제 효과와 미백 효과가 있음을 밝혀내어 본 발명을 완성하게 되었다.    Therefore, the present inventors have tried to develop a new whitening agent using a mouse melanoma cell (B16 mouse melanoma cell) that can screen even a substance that inhibits melanin synthesis induction itself, silanyl oxymethyl -Methyl imidazole derivatives have been found to have a very strong melanin production inhibitory effect and whitening effect to complete the present invention.

본 발명은 상기와 같은 종래의 문제점을 해결하기 위한 것으로서, 본 발명의 목적은 피부의 멜라닌 생성을 억제하는 멜라닌 생성 억제용 조성물을 제공하는 것이다.The present invention is to solve the conventional problems as described above, an object of the present invention is to provide a composition for inhibiting melanin production to inhibit melanin production of the skin.

본 발명의 다른 목적은 멜라닌의 생성을 억제함으로써 기미나 주근깨 개선 및 피부 미백 효과가 매우 우수한 피부 미백용 화장료 조성물을 제공하는 것이다.It is another object of the present invention to provide a cosmetic composition for skin whitening, which is excellent in reducing the melanin and improving freckles and freckles and skin whitening effect.

상기 목적을 달성하기 위하여, 본 발명은 하기 화학식 1로 표시되는 실라노일 옥시메틸-메틸 이미다졸 유도체를 유효성분으로 포함하는 멜라닌 생성 억제용 조성물을 제공한다.In order to achieve the above object, the present invention provides a composition for inhibiting melanin production comprising silanoyl oxymethyl-methyl imidazole derivative represented by the following formula (1) as an active ingredient.

또한, 본 발명은 하기 화학식 1로 표시되는 실라노일 옥시메틸-메틸 이미다졸 유도체를 유효성분으로 포함하는 피부 미백용 화장료 조성물을 제공한다.The present invention also provides a cosmetic composition for skin whitening comprising silanoyl oxymethyl-methyl imidazole derivative represented by the following formula (1) as an active ingredient.

Figure 112005015244690-PAT00002
Figure 112005015244690-PAT00002

(상기 식에서 R1, R2 및 R3는 서로 같거나 다른 것으로, 수소원자, C3 내지 C7의 직쇄 또는 분쇄형 알킬기, C2 내지 C7의 직쇄 또는 분쇄형 알케닐기 및 C5 내지 C7의 사이클로알케닐기로 이루어진 그룹 중에서 선택된 것이고, (Wherein R 1, R 2 and R 3 may be the same or different from each other, hydrogen atom, C 3 to C 7 straight or branched chain alkyl group, C 2 to C 7 linear or branched form of alkenyl groups and C 5 to C of Selected from the group consisting of 7 cycloalkenyl groups,

n은 0 또는 1의 정수이다.)n is an integer of 0 or 1.)

바람직하기로, 상기 R1, R2 및 R3는 수소원자, C1 내지 C4의 알킬기, C2 내지 C5의 알케닐기 및 페닐기로 이루어진 군에서 선택된 것이고, Preferably, R 1 , R 2 and R 3 are selected from the group consisting of a hydrogen atom, an alkyl group of C 1 to C 4 , an alkenyl group of C 2 to C 5 and a phenyl group,

n은 0 또는 1의 정수이다.n is an integer of 0 or 1.

더욱 바람직하기로, 본 발명에 따른 실라노일 옥시메틸-메틸 이미다졸 유도체는 하기와 같다: More preferably, the silanoyl oxymethyl-methyl imidazole derivatives according to the invention are as follows:

1) 터셔리부틸디페닐실란일옥시메틸-5-메틸-1-이미다졸1) tertiarybutyldiphenylsilaneyloxymethyl-5-methyl-1-imidazole

2) 디페닐실란일 옥시메틸-5-메틸-1-이미다졸2) diphenylsilaneyl oxymethyl-5-methyl-1-imidazole

3) 디메틸페닐실란일 옥시메틸-5-메틸-1-이미다졸3) dimethyldimethylsilaneyl oxymethyl-5-methyl-1-imidazole

4) 메틸트리페닐실란일옥시메틸--5-메틸-1-이미다졸4) methyltriphenylsilaneyloxymethyl--5-methyl-1-imidazole

5) 디페닐비닐실란일옥시메틸--5-메틸-1-이미다졸 5) diphenylvinylsilaneyloxymethyl--5-methyl-1-imidazole

6) 메틸-메틸페닐실란일옥시메틸--5-메틸-1-이미다졸6) methyl-methylphenylsilanyloxymethyl--5-methyl-1-imidazole

7) 메틸-메틸디페닐실란일옥시메틸--5-메틸-1-이미다졸7) methyl-methyldiphenylsilaneyloxymethyl--5-methyl-1-imidazole

8) 디메틸파라토일실란일옥시메틸--5-메틸-1-이미다졸8) Dimethylparatoylsilaneyloxymethyl--5-methyl-1-imidazole

이러한 화합물은 하기 표 1에 나타낸 바와 같다.Such compounds are as shown in Table 1 below.

화합물명Compound name 구조식constitutional formula 터셔리부틸디페닐실란일옥시메틸-5-메틸-1-이미다졸 Tertiarybutyldiphenylsilaneyloxymethyl-5-methyl-1-imidazole

Figure 112005015244690-PAT00003
Figure 112005015244690-PAT00003
디페닐실란일 옥시메틸-5-메틸-1-이미다졸Diphenylsilaneyl oxymethyl-5-methyl-1-imidazole
Figure 112005015244690-PAT00004
Figure 112005015244690-PAT00004
디메틸페닐실란일 옥시메틸-5-메틸-1-이미다졸Dimethylphenylsilanyl oxymethyl-5-methyl-1-imidazole
Figure 112005015244690-PAT00005
Figure 112005015244690-PAT00005
메틸트리페닐실란일옥시메틸--5-메틸-1-이미다졸 Methyltriphenylsilaneyloxymethyl--5-methyl-1-imidazole
Figure 112005015244690-PAT00006
Figure 112005015244690-PAT00006
디페닐비닐실란일옥시메틸--5-메틸-1-이미다졸 Diphenylvinylsilaneyloxymethyl--5-methyl-1-imidazole
Figure 112005015244690-PAT00007
Figure 112005015244690-PAT00007
메틸-메틸페닐실란일옥시메틸--5-메틸-1-이미다졸Methyl-methylphenylsilanyloxymethyl--5-methyl-1-imidazole
Figure 112005015244690-PAT00008
Figure 112005015244690-PAT00008
메틸-메틸디페닐실란일옥시메틸--5-메틸-1-이미다졸 Methyl-methyldiphenylsilaneyloxymethyl--5-methyl-1-imidazole
Figure 112005015244690-PAT00009
Figure 112005015244690-PAT00009
디메틸파라토일실란일옥시메틸--5-메틸-1-이미다졸Dimethylparatoylsilaneyloxymethyl--5-methyl-1-imidazole
Figure 112005015244690-PAT00010
Figure 112005015244690-PAT00010

상기 화학식 1로 표시되는 실라노일 옥시메틸-메틸 이미다졸 유도체는 이미 여러 문헌에 기재된 공지된 물질이나 아직까지 멜라닌 억제 효과에 대한 보고는 없다.The silanoyl oxymethyl-methyl imidazole derivatives represented by the formula (1) are known materials already described in various literatures, but there are no reports on melanin inhibitory effects.

이에, 상기 화학식 1의 실라노일 옥시메틸-메틸 이미다졸 유도체는 시판되는 것을 구입하여 사용하거나, 공지된 방법에 의해 제조 사용될 수 있으며, 정제하여 사용한다. 이때 사용되는 정제는 통상적으로 사용되는 칼럼크로마토그라피 및 고속액체크로마토그라피(HPLC) 등의 방법으로 수행가능하며, 이러한 방법에 한정되는 것은 아니다.Thus, the silanoyl oxymethyl-methyl imidazole derivatives of the formula (1) may be purchased and used commercially, or may be prepared and used by known methods, and may be purified. The purification used at this time can be carried out by methods such as commonly used column chromatography and high performance liquid chromatography (HPLC), but is not limited to these methods.

일예로, 상기 화학식 1로 표시되는 실라노일 옥시메틸-메틸 이미다졸 유도체는 하기 반응식 1에 기재한 바의 반응에 의해 제조된다.For example, the silanoyl oxymethyl-methyl imidazole derivative represented by Chemical Formula 1 is prepared by the reaction as described in Scheme 1 below.

Figure 112005015244690-PAT00011
Figure 112005015244690-PAT00011

(상기 식에서 R1, R2및 R3는 상기에서 정의한 바와 같으며, X는 할로겐 원소이다.)(Wherein R 1 , R 2 and R 3 are as defined above and X is a halogen element.)

바람직하기로, 상기 화학식 2로 표시되는 이미다졸 유도체와 화학식 3으로 표시되는 실란 화합물을 촉매 하에 용매에 용해시킨 다음, 20 내지 60 ℃의 온도에서 반응시켜 화학식 1로 표시되는 실라노일 옥시메틸-메틸 이미다졸 유도체를 제조한다.Preferably, the imidazole derivative represented by Chemical Formula 2 and the silane compound represented by Chemical Formula 3 are dissolved in a solvent under a catalyst, and then reacted at a temperature of 20 to 60 ° C. to silanoyl oxymethyl-methyl. Prepare imidazole derivatives.

바람직하기로, 상기 출발물질로 사용되는 화학식 2의 화합물은 t-부틸클로로디페닐실란, 클로로디페닐실란, 클로로디메틸페닐실란, 클로로트리페닐실란, 클로로디페닐비닐실란, 클로로메틸페닐실란, 클로로메틸디페닐실란 및 클로로디메틸토일실란으로 이루어진 그룹 중에서 적절히 선택하여 사용한다.Preferably, the compound of formula 2 used as the starting material is t-butylchlorodiphenylsilane, chlorodiphenylsilane, chlorodimethylphenylsilane, chlorotriphenylsilane, chlorodiphenylvinylsilane, chloromethylphenylsilane, chloromethyl It is suitably selected from the group consisting of diphenylsilane and chlorodimethyltoylsilane.

상기 화학식 1로 표시되는 실라노일 옥시메틸-메틸 이미다졸 유도체는 멜라닌 생성 억제 효과가 우수하여 멜라닌 생성 억제용 조성물 및 피부 미백용 화장료 조성물로서 인체에 적용함으로써, 우수한 멜라닌 생성 억제효과와 피부 미백 효과를 얻을 수 있다.The silanoyl oxymethyl-methyl imidazole derivative represented by Chemical Formula 1 is excellent in inhibiting melanin production and applied to the human body as a composition for inhibiting melanin production and a cosmetic composition for skin whitening, thereby providing excellent melanin production inhibitory effect and skin whitening effect. You can get it.

본 발명의 바람직한 실험예에 따르면 화학식 1의 실라노일 옥시메틸-메틸 이미다졸 유도체를 쥐의 멜라노마 세포(B-16 melanoma cell)에 처리하였을 때, 매우 강력한 멜라닌 생성 저해 효과를 나타냄을 알 수 있었다. 이러한 결과는 상기 실라노일 옥시메틸-메틸 이미다졸 유도체를 사람의 피부에 도포하여 피부 미백 효과를 나타냄을 의미한다. 더욱이 기존 공지된 여러 문헌을 통해 실라노일 옥시메틸-메틸 이미다졸 유도체가 인체에 안전함이 알려져 있어 멜라닌 생성 억제제 및 피부 미백제로 바람직하게 적용가능함을 알 수 있다. According to a preferred experimental example of the present invention, when treated with silanoyl oxymethyl-methyl imidazole derivatives of the formula (1) to rat melanoma cells (B-16 melanoma cells), it was found that exhibits a very strong melanin production inhibitory effect . This result means that the silanoyl oxymethyl-methyl imidazole derivative is applied to the skin of humans to exhibit skin whitening effect. Furthermore, it is known from the various known documents that silanoyl oxymethyl-methyl imidazole derivatives are known to be safe for humans, and thus they are preferably applicable as melanogenesis inhibitors and skin lightening agents.

본 발명에 따른 실라노일 옥시메틸-메틸 이미다졸 유도체는 멜라닌 생성 억제용 및 피부 미백용 화장료 조성물로서 피부에서의 활성 성분의 흡수도, 불활성화율, 배설속도, 사용자의 연령, 성별 및 상태 등에 따라 적절히 선택할 수 있으며, 바람직하기로 전체 중량 대비 0.000001 내지 10.0 중량% 포함할 수 있으며, 더욱 바 람직하게는 0.0001 내지 10 중량% 포함할 수 있고, 더욱 바람직하게는 0.01 내지 10 중량%를 포함할 수 있다. 만약, 상기 실라노일 옥시메틸-메틸 이미다졸 유도체의 함량이 0.0001 중량% 미만인 경우에는 뚜렷한 효과를 기대할 수 없고, 10 중량%를 초과하는 경우에는 포함량의 증가에 비해 효과의 증가가 미치지 못한다. The silanoyl oxymethyl-methyl imidazole derivative according to the present invention is a cosmetic composition for inhibiting melanin production and skin whitening, and is appropriately selected according to the absorption, inactivation rate, excretion rate, age, sex and condition of the active ingredient in the skin. Can be selected, preferably 0.000001 of the total weight. To 10.0% by weight, more preferably 0.0001 to 10% by weight, and more preferably 0.01 to 10% by weight. If the content of the silanoyl oxymethyl-methyl imidazole derivative is 0.0001 If it is less than the weight%, no obvious effect can be expected, and if it exceeds 10% by weight, the effect is not increased compared to the increase in the amount of inclusion.

본 발명에 따른 멜라닌 생성 억제용 조성물 및 피부 미백용 화장료 조성물은 외용연고, 크림, 폼, 화장수, 팩, 유연수, 유액, 파운데이션, 메이크업베이스, 엣센스, 비누, 액체세정료, 입욕제, 선 스크린크림, 또는 선오일 등의 제형으로 제조할 수 있다.The composition for inhibiting melanin production and the cosmetic composition for skin whitening according to the present invention include an external ointment, a cream, a foam, a lotion, a pack, a soft water, an emulsion, a foundation, a makeup base, an essence, a soap, a liquid detergent, a bath, a sunscreen cream, Or it may be prepared in a formulation such as sun oil.

또한 본 발명의 멜라닌 생성 억제용 조성물 및 피부 미백용 화장료 조성물은 일반 피부화장료에 배합되는 통상의 성분, 예를 들면 유분, 물, 계면활성제, 보습제, 저급알콜, 증점제, 킬레이트제, 색소, 방부제, 향료 등을 적절히 배합할 수 있다.In addition, the composition for inhibiting melanin production of the present invention and the cosmetic composition for skin whitening are common ingredients, for example, oil, water, surfactant, moisturizer, lower alcohol, thickener, chelating agent, coloring agent, preservative, A fragrance etc. can be mix | blended suitably.

이하 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시하나, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다.Hereinafter, preferred examples are provided to help understanding of the present invention, but the following examples are merely to illustrate the present invention, and the scope of the present invention is not limited to the following examples.

제조예 1: 터셔리부틸디페닐실란일옥시메틸-5-메틸-1-이미다졸(4-(t-butyldiphenylsilanyloxymethyl)-5-methyl-1H-imidazole)의 제조Preparation Example 1: Preparation of tert-butyldiphenylsilanyloxymethyl-5-methyl-1-imidazole (4- (t-butyldiphenylsilanyloxymethyl) -5-methyl-1H-imidazole)

하기 반응식 2에 따라 터셔리부틸디페닐실란일옥시메틸-5-메틸-1-이미다졸을 제조하였다.Tertiarybutyldiphenylsilaneyloxymethyl-5-methyl-1-imidazole was prepared according to Scheme 2 below.

Figure 112005015244690-PAT00012
Figure 112005015244690-PAT00012

먼저, 옥시메틸-5-메틸이미다졸(oxymethyl-5-methyl-1H-imidazole) 1.5g을 테트라하이드로퓨란(Tetrahydrofuran) 150ml에 녹이고 트리에칠아민(Triethylamine) 2.9ml을 적하하고 5분간 교반한 후 t-부틸클로로디페닐실란(tert-butyl-chloro-diphenylsilane) 2.84ml을 첨가하고 실온에서 교반하였다. 이어서, 출발물질이 완전히 사라지면 에칠아세테이트(Ethylacetate) 150ml을 첨가하고 물 100ml로 2-3회 씻어준 후 무수마그네슘설페이트(Anhydrous Magnesium Sulfate)로 수분을 제거하였다. First, 1.5 g of oxymethyl-5-methyl imidazole was dissolved in 150 ml of tetrahydrofuran, 2.9 ml of triethylamine was added dropwise, and stirred for 5 minutes. Then, 2.84 ml of t-butylchlorodiphenylsilane (tert-butyl-chloro-diphenylsilane) was added and stirred at room temperature. Subsequently, when the starting material disappeared completely, 150 ml of ethylacetate was added, washed 2-3 times with 100 ml of water, and water was removed with anhydrous magnesium sulfate (Anhydrous Magnesium Sulfate).

다음으로, 유기용매를 감압 증류한 후 관크로마토그라피(실리카젤: 230-400메쉬)를 이용하여 반응생성물 2.8g(수율 77%)을 얻어 핵자기공명분석(1H-NMR) 및 질량분석으로 확인하였다.Subsequently, the organic solvent was distilled under reduced pressure, and then tube chromatography (silica gel: 230-400 mesh) was used to obtain 2.8 g (yield 77%) of the reaction product by nuclear magnetic resonance analysis ( 1 H-NMR) and mass spectrometry. Confirmed.

1H NMR (CDCl3, 300 MHz) δ 7.65(m, 4H), 7.55(s, 1H), 7.42(m, 7H), 4.68(s, 2H), 2.04(s, 3H), 1.07(s, 9H) 1 H NMR (CDCl 3 , 300 MHz) δ 7.65 (m, 4H), 7.55 (s, 1H), 7.42 (m, 7H), 4.68 (s, 2H), 2.04 (s, 3H), 1.07 (s, 9H)

MS = 351 (M + H+)MS = 351 (M + H + )

제조예 2: 디페닐실란일 옥시메틸-5-메틸-1-이미다졸(4-diphenylsilanyloxymethyl-5-methyl-1H-imidazole)의 제조Preparation Example 2 Preparation of 4-Diphenylsilanyloxymethyl-5-methyl-1H-imidazole

하기 반응식 3에 나타낸 바와 같이, t-부틸클로로디페닐실란(tert-butyl-chloro-diphenylsilane) 대신에 클로로디페닐실란(chlorodiphenylsilane)을 사용하는 것을 제외하고 실시예 1과 동일한 방법을 사용하여 목적물(2.9g, 수율 76%)을 얻어 핵자기공명분석(1H-NMR) 및 질량분석으로 확인하였다.As shown in Scheme 3 below, using the same method as in Example 1 except for using chlorodiphenylsilane instead of t-butylchlorodiphenylsilane (tert-butyl-chloro-diphenylsilane) 2.9 g, yield 76%) was obtained by nuclear magnetic resonance analysis ( 1 H-NMR) and mass spectrometry.

Figure 112005015244690-PAT00013
Figure 112005015244690-PAT00013

1H NMR (CDCl3, 300 MHz) δ7.54-7.36(m, 9H), 7.18(m, 1H), 4.79(s, 2H), 2.359s, 3H). 1 H NMR (CDCl 3 , 300 MHz) δ 7.54-7.36 (m, 9H), 7.18 (m, 1H), 4.79 (s, 2H), 2.359 s, 3H).

MS = 295 (M + H+)MS = 295 (M + H + )

제조예 3: 디메틸페닐실란일 옥시메틸-5-메틸-1-이미다졸(4-dimethylphenylsilanyloxymethyl-5-methyl-1H-imidazole)의 제조Preparation Example 3: Preparation of dimethylphenylsilanyl oxymethyl-5-methyl-1-imidazole (4-dimethylphenylsilanyloxymethyl-5-methyl-1H-imidazole)

하기 반응식 4에 나타낸 바와 같이, t-부틸클로로디페닐실란(tert-butyl-chloro-diphenylsilane) 대신에 클로로디메틸페닐실란 (chlorodimethylphenylsilane)을 사용하는 것을 제외하고 실시예 1과 동일한 방법을 사용하여 목적물(2.8g, 수율 66%)을 얻어 핵자기공명분석(1H-NMR) 및 질량분석으로 확인하였다.As shown in Reaction Scheme 4, the target product was used in the same manner as in Example 1 except for using chlorodimethylphenylsilane instead of tert-butyl-chloro-diphenylsilane. 2.8 g, yield 66%) was obtained by nuclear magnetic resonance analysis ( 1 H-NMR) and mass spectrometry.

Figure 112005015244690-PAT00014
Figure 112005015244690-PAT00014

1H NMR (CDCl3, 300 MHz) δ7.30(m, 5H), 7.18(m, 1H), 5.05(s, 2H), 2.35(s, 3H). 1 H NMR (CDCl 3 , 300 MHz) δ 7.30 (m, 5H), 7.18 (m, 1H), 5.05 (s, 2H), 2.35 (s, 3H).

MS = 360 (M + H+)MS = 360 (M + H + )

제조예4 : 메틸트리페닐실란일옥시메틸-5-메틸-1-이미다졸(5-Methyl-4-triphenylsilanyloxymethyl-5-methyl-1Preparation Example 4 Methyltriphenylsilanyloxymethyl-5-methyl-1-imidazole (5-Methyl-4-triphenylsilanyloxymethyl-5-methyl-1 HH -imidazole)의 제조-imidazole)

하기 반응식 5에 나타낸 바와 같이, t-부틸클로로디페닐실란(tert-butyl-chloro-diphenylsilane) 대신에 클로로트리페닐실란(chlorotriphenylsilane)을 사용하는 것을 제외하고 실시예 1과 동일한 방법을 사용하여 목적물(2.7g, 수율 76%)을 얻어 핵자기공명분석(1H-NMR) 및 질량분석으로 확인하였다.As shown in Scheme 5 below, the target product was prepared in the same manner as in Example 1 except for using chlorotriphenylsilane instead of tert-butyl-chloro-diphenylsilane. 2.7 g, yield 76%) was obtained by nuclear magnetic resonance analysis ( 1 H-NMR) and mass spectrometry.

Figure 112005015244690-PAT00015
Figure 112005015244690-PAT00015

1H NMR (CDCl3, 300 MHz) δ7.54-7.36(m, 15H), 7.18(m, 1H), 5.05(s, 2H), 2.35(s, 3H). 1 H NMR (CDCl 3 , 300 MHz) δ 7.54-7.36 (m, 15H), 7.18 (m, 1H), 5.05 (s, 2H), 2.35 (s, 3H).

MS = 233 (M + H+)MS = 233 (M + H + )

제조예 5: 디페닐비닐실란일옥시메틸-5-메틸-1-이미다졸(4-(Diphenylvinylsilanyloxymethyl)-5-methyl-1Preparation Example 5 Diphenylvinyl silanyloxymethyl-5-methyl-1-imidazole (4- (Diphenylvinylsilanyloxymethyl) -5-methyl-1 HH -imidazole)의 제조-imidazole)

하기 반응식 6에 나타낸 바와 같이, t-부틸클로로디페닐실란(tert-butyl-chloro-diphenylsilane) 대신에 클로로디페닐비닐실란(chlorodiphenylvinylsilane)을 사용하는 것을 제외하고 실시예 1과 동일한 방법을 사용하여 목적물(3.1, 수율 83%)을 얻어 핵자기공명분석(1H-NMR) 및 질량분석으로 확인하였다.As shown in Scheme 6 below, the target product was used in the same manner as in Example 1 except for using chlorodiphenylvinylsilane instead of tert-butyl-chloro-diphenylsilane. (3.1, yield 83%) was obtained and confirmed by nuclear magnetic resonance analysis ( 1 H-NMR) and mass spectrometry.

Figure 112005015244690-PAT00016
Figure 112005015244690-PAT00016

1H NMR (CDCl3, 300 MHz) δ7.54-7.36(m, 11H), 7.18(m, 1H), 5.20(m, 1H), 5.05(s, 2H), 2.35(s, 3H). 1 H NMR (CDCl 3 , 300 MHz) δ 7.54-7.36 (m, 11H), 7.18 (m, 1H), 5.20 (m, 1H), 5.05 (s, 2H), 2.35 (s, 3H).

MS = 309 (M + H+)MS = 309 (M + H + )

제조예 6: 5-메틸(4-메틸페닐실란일옥시메틸-5-메틸-1-이미다졸) (5-Methyl-4-(methylpheylsilanyloxymethyl)-5-methyl-1Preparation Example 6 5-methyl (4-methylphenylsilanyloxymethyl-5-methyl-1-imidazole) (5-Methyl-4- (methylpheylsilanyloxymethyl) -5-methyl-1 HH -imidazole)의 제조-imidazole)

하기 반응식 7에 나타낸 바와 같이, t-부틸클로로디페닐실란(tert-butyl-chloro-diphenylsilane) 대신에 클로로메틸페닐실란(chloromethylphenylsilane)을 사용하는 것을 제외하고 실시예 1과 동일한 방법을 사용하여 목적물(3.3g, 수율 78%)을 얻어 핵자기공명분석(1H-NMR) 및 질량분석으로 확인하였다.As shown in Scheme 7 below, the target product (3.3) was used in the same manner as in Example 1 except for using chloromethylphenylsilane instead of tert-butyl-chloro-diphenylsilane. g, yield 78%) was obtained by nuclear magnetic resonance analysis ( 1 H-NMR) and mass spectrometry.

Figure 112005015244690-PAT00017
Figure 112005015244690-PAT00017

1H NMR (CDCl3, 300 MHz) δ7.30(m, 5H), 7.18(m, 1H), 4.80(s, 2H), 2.35(s, 3H), 0.66(s, 3H). 1 H NMR (CDCl 3 , 300 MHz) δ 7.30 (m, 5H), 7.18 (m, 1H), 4.80 (s, 2H), 2.35 (s, 3H), 0.66 (s, 3H).

MS = 233 (M + H+)MS = 233 (M + H + )

제조예 7: 5-(4-메틸-메틸디페닐실란일옥시메틸-5-메틸-1-이미다졸) (5-Methyl-4- (methyldiphenylsilanyloxymethyl)-5-methyl-1Preparation Example 7 5- (4-Methyl-methyldiphenylsilanyloxymethyl-5-methyl-1-imidazole) (5-Methyl-4- (methyldiphenylsilanyloxymethyl) -5-methyl-1 HH -imidazole)의 제조-imidazole)

하기 반응식 8에 나타낸 바와 같이, t-부틸클로로디페닐실란(tert-butyl-chloro-diphenylsilane) 대신에 클로로메틸디페닐실란(ch loromethyldiphenylsilane)을 사용하는 것을 제외하고 실시예 1과 동일한 방법을 사용하여 목적물(2.5g, 수율 66%)을 얻어 핵자기공명분석(1H-NMR) 및 질량분석으로 확인하였다.As shown in Scheme 8 below, the same method as in Example 1 was used except that chloromethyldiphenylsilane was used instead of tert-butyl-chloro-diphenylsilane. The target product (2.5 g, yield 66%) was obtained and confirmed by nuclear magnetic resonance analysis ( 1 H-NMR) and mass spectrometry.

Figure 112005015244690-PAT00018
Figure 112005015244690-PAT00018

1H NMR (CDCl3, 300 MHz) δ7.54-7.36(m, 10H), 7.18(m, 1H), 5.05(s, 2H), 2.35(s, 3H), 0.66(s, 3H). 1 H NMR (CDCl 3 , 300 MHz) δ 7.54-7.36 (m, 10H), 7.18 (m, 1H), 5.05 (s, 2H), 2.35 (s, 3H), 0.66 (s, 3H).

MS = 360 (M + H+)MS = 360 (M + H + )

제조예 8 : 디메틸파라토일실란일옥시메틸-5-메틸-1-이미다졸 (4-(Dimethyl-p-tolylsilanyloxymethyl)-5-methyl-1Preparation Example 8: Dimethyl paratoyl silanyl oxymethyl-5-methyl-1-imidazole (4- (Dimethyl-p-tolylsilanyloxymethyl) -5-methyl-1 HH -imidazole)의 제조-imidazole)

하기 반응식 9에 나타낸 바와 같이, t-부틸클로로디페닐실란(tert-butyl-chloro-diphenylsilane) 대신에 클로로디메틸토일실란(chlorodimethyltoylsilane)을 사용하는 것을 제외하고 실시예 1과 동일한 방법을 사용하여 목적물(2.8g, 수율 70%)을 얻어 핵자기공명분석(1H-NMR) 및 질량분석으로 확인하였다.As shown in Scheme 9 below, using the same method as in Example 1 except for using chlorodimethyltoylsilane instead of tert-butyl-chloro-diphenylsilane 2.8 g, yield 70%) was obtained by nuclear magnetic resonance analysis ( 1 H-NMR) and mass spectrometry.

Figure 112005015244690-PAT00019
Figure 112005015244690-PAT00019

1H NMR (CDCl3, 300 MHz) δ7.30(m, 5H), 7.18(m, 1H), 5.05(s, 2H), 2.35(s, 3H), 0.66(s, 6H). 1 H NMR (CDCl 3 , 300 MHz) δ 7.30 (m, 5H), 7.18 (m, 1H), 5.05 (s, 2H), 2.35 (s, 3H), 0.66 (s, 6H).

MS = 247 (M + H+)MS = 247 (M + H + )

실험예 1 : 멜라닌 생성 저해 효과Experimental Example 1 melanin production inhibitory effect

상기 제조예 1 내지 9에서 얻어진 실라노일 옥시메틸-메틸 이미다졸 유도체를 쥐의 멜라노마 세포(B-16 mouse melanoma cell)의 배양액에 첨가하여 세포 수준에서의 미백 효과를 실험하였다.(Lotan R., Lotan D. Cancer Res. 40:3345-3350, 1980).    The silanoyl oxymethyl-methyl imidazole derivatives obtained in Preparation Examples 1 to 9 were added to the culture medium of B-16 mouse melanoma cells to test the whitening effect at the cellular level. (Lotan R. , Lotan D. Cancer Res. 40: 3345-3350, 1980).

이때 실라노일 옥시메틸-메틸 이미다졸 유도체를 최종농도가 2mg/ml가 되도록 하여 하이드로퀴논 수용액과 함께 각각 B-16멜라노마 세포의 배양배지에 첨가하여 3일간 배양한 후 세포들을 트립신(trypsin)처리하여 배양용기로부터 떼어내 원심분리한 후 멜라닌을 추출하였다. 여기에 수산화 나트륨 용액(1N농도) 1ml를 가 하여 10분간 끓여 멜라닌을 녹이고 분광 광도계를 이용, 400나노미터(nm)에서 흡광도를 측정하여 생성된 멜라닌의 양을 단위 세포수당(106 cell)의 흡광도로 나타내는 방법으로 수행하였으며, 대조군에 대한 상대적인 멜라닌 생성량을 저해율(%)로 계산하고 결과를 하기 표 2에 나타내었다.At this time, the silanoyl oxymethyl-methyl imidazole derivative was added to a culture medium of B-16 melanoma cells with a hydroquinone solution, respectively, in a final concentration of 2 mg / ml, and then cultured for 3 days, followed by trypsin treatment. After removing from the culture vessel by centrifugation, melanin was extracted. Add 1 ml of sodium hydroxide solution (1N concentration), boil for 10 minutes to dissolve melanin, and measure the absorbance at 400 nanometer (nm) using a spectrophotometer to determine the amount of melanin produced per unit cell count (10 6 cells). It was carried out by the method represented by the absorbance, the relative melanin production relative to the control was calculated as the inhibition rate (%) and the results are shown in Table 2 below.

농도에 따른 세포수준에서의 멜라닌 생성 저해효과 Inhibitory effect of melanin production at the cellular level 시료sample 멜라닌생성량Melanin production 저해율(%)% Inhibition 대조군(무첨가)Control group (no addition) 0.04±0.0040.04 ± 0.004 -- 제조예 1Preparation Example 1 0.016±0.0020.016 ± 0.002 66%66% 제조예 2Preparation Example 2 0.015±0.0020.015 ± 0.002 68%68% 제조예 3Preparation Example 3 0.017±0.0010.017 ± 0.001 64%64% 제조예 4Preparation Example 4 0.020±0.0020.020 ± 0.002 57%57% 제조예 5Preparation Example 5 0.018±0.0020.018 ± 0.002 62%62% 제조예 6Preparation Example 6 0.018±0.0020.018 ± 0.002 62%62% 제조예 7Preparation Example 7 0.021±0.0010.021 ± 0.001 55%55% 제조예 8Preparation Example 8 0.020±0.0020.020 ± 0.002 57%57% 하이드로퀴논 (1ug/ml)Hydroquinone (1ug / ml) 0.025±0.0020.025 ± 0.002 47%47%

* 반복수 = 3 * Number of iterations = 3

상기 표 2에 따르면, 본 발명에서 제시한 실라노일 옥시메틸-메틸 이미다졸 유도체는 기존에 알려진 미백 물질인 하이드로퀴논과 비교할 때 배양된 쥐의 멜라노마 세포에 대하여 대등한 멜라닌 생성 억제능이 있음을 알 수 있다.  According to Table 2, the silanoyl oxymethyl-methyl imidazole derivatives presented in the present invention have comparable melanin production inhibitory ability against cultured mouse melanoma cells when compared with hydroquinone, a known whitening substance. Can be.

이하 본 발명에 따른 실라노일 옥시메틸-메틸 이미다졸을 함유하는 화장료의 처방예를 하기 제제예에 의해 나타내었다.Hereinafter, the formulation example of the cosmetic containing silanoyl oxymethyl-methyl imidazole which concerns on this invention is shown by the following formulation example.

제제예 1 내지 8 및 비교예 1: 피부 미백용 외용연고Formulation Examples 1 to 8 and Comparative Example 1: External Ointment for Skin Whitening

성분 ingredient 제조예(중량%)Production example (% by weight) 비교예Comparative example 1One 22 33 44 55 66 77 88 1One 스테아린산Stearic acid 15.015.0 15.015.0 15.015.0 15.015.0 15.015.0 15.015.0 15.015.0 15.015.0 15.015.0 세탄올Cetanol 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 수산화칼륨Potassium hydroxide 0.70.7 0.70.7 0.70.7 0.70.7 0.70.7 0.70.7 0.70.7 0.70.7 0.70.7 0글리세린0 glycerin 5.05.0 5.05.0 5.05.0 5.05.0 5.05.0 5.05.0 5.05.0 5.05.0 5.05.0 프로필렌그리콜Propylene glycol 3.03.0 3.03.0 3.03.0 3.03.0 3.03.0 3.03.0 3.03.0 3.03.0 3.03.0 방부제antiseptic 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity incense 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 적량Quantity 정제수Purified water to 100to 100 to 100to 100 to 100to 100 to 100to 100 to 100to 100 to 100to 100 to 100to 100 to 100to 100 to100to100 제조예 1Preparation Example 1 0.30.3 -- -- -- -- -- -- -- -- 제조예 2Preparation Example 2 -- 0.30.3 -- -- -- -- -- -- -- 제조예 3Preparation Example 3 -- -- 0.30.3 -- -- -- -- -- -- 제조예 4Preparation Example 4 -- -- -- 0.30.3 -- -- -- -- -- 제조예 5Preparation Example 5 -- -- -- -- 0.30.3 -- -- -- -- 제조예 6Preparation Example 6 -- -- -- -- -- 0.30.3 -- -- -- 제조예 7Preparation Example 7 -- -- -- -- -- -- 0.30.3 -- -- 제조예 8Preparation Example 8 -- -- -- -- -- -- -- 0.30.3 --

실험예 2 : 색소 침착 측정Experimental Example 2: Pigmentation Measurement

상기 제형에에서 제조된 크림의 색소 침착정도를 알아보기 위해 하기와 같이 실시하였다.To determine the degree of pigmentation of the cream prepared in the formulation was carried out as follows.

건강한 남여 20명을 선정하여 양팔의 하박부에 직경 7mm크기의 구멍이 6개씩 2줄로 파인 알루미늄 호일을 붙이고, 팔에서 10cm 떨어진 거리에서 ORIEL solar simulator 1000W를 사용하여 60mJ/cm2의 광량을 조사하였다.20 healthy males and females were placed in the lower hips of each arm with 6 holes of 7 mm diameter in two rows of aluminum foil, and 60mJ / cm 2 light was irradiated using ORIEL solar simulator 1000W at a distance of 10cm from the arm. .

조사 전에 70% 에탄올 수용액으로 조사 부위를 잘 세척하였으며, 조사하기 3일전부터 조사 후 3주째까지 1일 2회씩 제조예 1 내지 8 및 비교예 1에 따라 제조된 기제를 한 쌍으로 같은 줄에 도포하였다 The irradiated site was well washed with 70% aqueous ethanol solution before irradiation, and twice a day from 3 days before irradiation to 3 weeks after irradiation, and a pair of bases prepared according to Preparation Examples 1 to 8 and Comparative Example 1 were applied to the same row in pairs. Was

이때 각각에 대하여 제조예와 비교예의 색소침착도를 육안으로 판정하고, 제조예가 비교예에 비해 색소침착을 억제한 정도를 '효과있음','효과없음'의 2단계로 평가하였으며, 얻어진 결과를 하기 표 4에 나타내었다.In each case, the degree of pigmentation of the preparation example and the comparative example was visually determined, and the degree of suppression of the pigmentation of the preparation example compared to the comparative example was evaluated in two stages of 'effective' and 'no effect'. It is shown in Table 4 below.

실라노일 옥시메틸-메틸 이미다졸 유도체를 함유한 크림의 색소 침착 저해 효과 Pigmentation Inhibitory Effects of Creams Containing Silanoyl Oxymethyl-Methyl Imidazole Derivatives 실험물질Experimental substance 효과있음(명)Effective (persons) 차이없음(명)No difference (persons) 제제예 1Formulation Example 1 1111 99 제제예 2Formulation Example 2 1010 1010 제제예 3Formulation Example 3 1010 1010 제제예 4Formulation Example 4 1111 99 제제예 5Formulation Example 5 1010 1010 제제예 6Formulation Example 6 1212 88 제제예 7Formulation Example 7 1010 1010 제제예 8Formulation Example 8 1212 88

상기 표 4에 나타낸 바와 같이, 본 발명에 따라 제조예 1 내지 8에 따라 제조된 실라노일 옥시메틸-메틸 이미다졸 유도체를 함유하는 크림은 피시험자 20명 중에서 최소 10명 이상에 대하여 미백 효과를 나타내었으며, 피부내에서 어떤 부작용도 나타나지 않았다. 이러한 결과는 본 발명에서 제시한 실라노일 옥시메틸-메틸 이미다졸 유도체가 안전하고 효과가 매우 뛰어난 기미나 주근깨 개선 또는 피부 미백제임을 보여준다.As shown in Table 4, the cream containing silanoyl oxymethyl-methyl imidazole derivatives prepared according to Preparation Examples 1 to 8 according to the present invention exhibits a whitening effect on at least 10 or more of 20 subjects. And no adverse effect was observed in the skin. These results show that the silanoyl oxymethyl-methyl imidazole derivatives presented in the present invention are safe and highly effective blemishes or freckles improving or skin whitening agents.

본 발명의 멜라닌 생성 억제용 조성물 및 피부 미백용 화장료 조성물은 실라노일 옥시메틸-메틸 이미다졸 유도체를 유효성분으로 포함함으로써, 피부의 멜라닌 생성을 억제하고, 기미나 주근깨 개선 및 피부 미백 효과가 매우 우수하여 멜라닌 생성 억제제 및 피부 미백제로 바람직하게 사용된다.The composition for inhibiting melanin production and the cosmetic composition for skin whitening of the present invention include silanoyl oxymethyl-methyl imidazole derivatives as an active ingredient, thereby inhibiting melanin production of the skin, and improving blemishes and freckles, and skin whitening effects are very excellent. It is preferably used as a melanogenesis inhibitor and skin lightening agent.

Claims (10)

하기 화학식 1로 표시되는 실라노일 옥시메틸-메틸 이미다졸 유도체를 유효 성분으로 포함하는 멜라닌 생성 억제용 조성물:Melanin production inhibiting composition comprising a silanoyl oxymethyl-methyl imidazole derivative represented by the following formula (1) as an active ingredient: [화학식 1][Formula 1]
Figure 112005015244690-PAT00020
Figure 112005015244690-PAT00020
상기 식에서 R1, R2 및 R3는 서로 같거나 다른 것으로, 수소원자, C3 내지 C7의 직쇄 또는 분쇄형 알킬기, C2 내지 C7의 직쇄 또는 분쇄형 알케닐기 및 C5 내지 C7의 사이클로알케닐기로 이루어진 그룹 중에서 선택된 것이고, Wherein R 1, R 2 and R 3 are each the same or different to a hydrogen atom, C 3 to C 7 of the straight or branched chain alkyl group, C 2 to C 7 straight or branched chain type alkenyl groups and C 5 to C 7 of the Is selected from the group consisting of cycloalkenyl groups, n은 0 또는 1의 정수이다.n is an integer of 0 or 1.
제 1 항에 있어서, 상기 R1, R2 및 R3는 수소원자, C1 내지 C4의 알킬기, C2 내지 C5의 알케닐기, 및 페닐기로 이루어진 군에서 선택된 것이고, The method according to claim 1, wherein R 1 , R 2 and R 3 is selected from the group consisting of a hydrogen atom, an alkyl group of C 1 to C 4 , an alkenyl group of C 2 to C 5 , and a phenyl group, n은 0 또는 1의 정수인 것을 특징으로 하는 멜라닌 생성 억제용 조성물.n is a composition for inhibiting melanin production, characterized in that an integer of 0 or 1. 제 1 항에 있어서, 상기 실라노일 옥시메틸-메틸 이미다졸 유도체는,The method of claim 1, wherein the silanoyl oxymethyl-methyl imidazole derivative, 1) 터셔리부틸디페닐실란일옥시메틸-5-메틸-1-이미다졸;1) tertiarybutyldiphenylsilaneyloxymethyl-5-methyl-1-imidazole; 2) 디페닐실란일 옥시메틸-5-메틸-1-이미다졸;2) diphenylsilaneyl oxymethyl-5-methyl-1-imidazole; 3) 디메틸페닐실란일 옥시메틸-5-메틸-1-이미다졸;3) dimethylphenylsilaneyl oxymethyl-5-methyl-1-imidazole; 4) 메틸트리페닐실란일옥시메틸--5-메틸-1-이미다졸;4) methyltriphenylsilaneyloxymethyl- 5-methyl-1-imidazole; 5) 디페닐비닐실란일옥시메틸--5-메틸-1-이미다졸; 5) diphenylvinylsilanyloxymethyl- 5-methyl-1-imidazole; 6) 메틸-메틸페닐실란일옥시메틸--5-메틸-1-이미다졸;6) methyl-methylphenylsilanyloxymethyl- 5-methyl-1-imidazole; 7) 메틸-메틸디페닐실란일옥시메틸--5-메틸-1-이미다졸; 및7) methyl-methyldiphenylsilaneyloxymethyl- 5-methyl-1-imidazole; And 8) 디메틸파라토일실란일옥시메틸--5-메틸-1-이미다졸로 이루어진 그룹 중에서 선택된 것을 특징으로 하는 멜라닌 생성 억제용 조성물.8) Dimethyl paratoyl silanyl oxymethyl- 5-methyl-1-imidazol composition for inhibiting melanin production, characterized in that selected from the group consisting of. 제 1 항에 있어서, 상기 멜라닌 생성 억제용 조성물은 실라노일 옥시메틸-메틸 이미다졸 유도체를 전체 조성물 중량에 대하여 0.000001 내지 10 중량% 포함하는 것을 특징으로 하는 멜라닌 생성 억제용 조성물.The composition for inhibiting melanin production according to claim 1, wherein the composition for inhibiting melanin production comprises 0.000001 to 10% by weight of silanoyl oxymethyl-methyl imidazole derivative based on the total weight of the composition. 제 1항에 있어서, 상기 멜라닌 생성 억제용 조성물은 외용연고, 크림, 폼, 화장수, 팩, 유연수, 유액, 파운데이션, 메이크업베이스, 엣센스, 비누, 액체세정료, 입욕제, 선 스크린크림, 및 선오일로 이루어진 군으로부터 선택되는 제형을 갖는 멜라닌 생성 억제용 조성물.The composition of claim 1, wherein the composition for inhibiting melanin production is an external ointment, cream, foam, lotion, pack, soft water, latex, foundation, makeup base, essence, soap, liquid cleanser, bath agent, sunscreen cream, and sun oil. Melanin inhibiting composition having a formulation selected from the group consisting of. 하기 화학식 1로 표시되는 실라노일 옥시메틸-메틸 이미다졸 유도체를 유효 성분으로 포함하는 피부 미백용 화장료 조성물:Cosmetic composition for skin whitening comprising silanoyl oxymethyl-methyl imidazole derivative represented by the following formula (1) as an active ingredient: [화학식 1][Formula 1]
Figure 112005015244690-PAT00021
Figure 112005015244690-PAT00021
상기 식에서 R1, R2 및 R3는 서로 같거나 다른 것으로, 수소원자, C3 내지 C7의 직쇄 또는 분쇄형 알킬기, C2 내지 C7의 직쇄 또는 분쇄형 알케닐기 및 C5 내지 C7의 사이클로알케닐기로 이루어진 그룹 중에서 선택된 것이고, Wherein R 1, R 2 and R 3 are each the same or different to a hydrogen atom, C 3 to C 7 of the straight or branched chain alkyl group, C 2 to C 7 straight or branched chain type alkenyl groups and C 5 to C 7 of the Is selected from the group consisting of cycloalkenyl groups, n은 0 또는 1의 정수이다.n is an integer of 0 or 1.
제 6 항에 있어서, 상기 R1, R2 및 R3는 수소원자, C1 내지 C4의 알킬기, C2 내지 C5의 알케닐기 및 페닐기로 이루어진 군에서 선택된 것이고, The method according to claim 6, wherein R 1 , R 2 and R 3 is selected from the group consisting of a hydrogen atom, an alkyl group of C 1 to C 4 , an alkenyl group of C 2 to C 5 and a phenyl group, n은 0 또는 1의 정수인 것을 특징으로 하는 피부 미백용 화장료 조성물.n is an integer of 0 or 1, the cosmetic composition for skin whitening. 제 6 항에 있어서, 상기 실라노일 옥시메틸-메틸 이미다졸 유도체는,The method of claim 6, wherein the silanoyl oxymethyl-methyl imidazole derivative, 1) 터셔리부틸디페닐실란일옥시메틸-5-메틸-1-이미다졸;1) tertiarybutyldiphenylsilaneyloxymethyl-5-methyl-1-imidazole; 2) 디페닐실란일 옥시메틸-5-메틸-1-이미다졸;2) diphenylsilaneyl oxymethyl-5-methyl-1-imidazole; 3) 디메틸페닐실란일 옥시메틸-5-메틸-1-이미다졸;3) dimethylphenylsilaneyl oxymethyl-5-methyl-1-imidazole; 4) 메틸트리페닐실란일옥시메틸--5-메틸-1-이미다졸;4) methyltriphenylsilaneyloxymethyl- 5-methyl-1-imidazole; 5) 디페닐비닐실란일옥시메틸--5-메틸-1-이미다졸; 5) diphenylvinylsilanyloxymethyl- 5-methyl-1-imidazole; 6) 메틸-메틸페닐실란일옥시메틸--5-메틸-1-이미다졸;6) methyl-methylphenylsilanyloxymethyl- 5-methyl-1-imidazole; 7) 메틸-메틸디페닐실란일옥시메틸--5-메틸-1-이미다졸; 및7) methyl-methyldiphenylsilaneyloxymethyl- 5-methyl-1-imidazole; And 8) 디메틸파라토일실란일옥시메틸--5-메틸-1-이미다졸로 이루어진 그룹 중에서 선택된 것을 특징으로 하는 피부 미백용 화장료 조성물.8) Dimethyl paratoyl silanyl oxymethyl- 5-methyl-1-imidazol Cosmetic composition for skin whitening, characterized in that selected from the group consisting of. 제 6 항에 있어서, 상기 피부 미백용 화장료 조성물은 실라노일 옥시메틸-메틸 이미다졸 유도체를 전체 조성물 중량에 대하여 0.000001 내지 10 중량% 포함하는 것을 특징으로 하는 피부 미백용 화장료 조성물.The cosmetic composition for skin whitening according to claim 6, wherein the cosmetic composition for skin whitening comprises silanoyl oxymethyl-methyl imidazole derivatives in an amount of 0.000001 to 10% by weight based on the total weight of the composition. 제 6항에 있어서, 상기 피부 미백용 화장료 조성물은 외용연고, 크림, 폼, 화장수, 팩, 유연수, 유액, 파운데이션, 메이크업베이스, 엣센스, 비누, 액체세정료, 입욕제, 선 스크린크림, 및 선오일로 이루어진 군으로부터 선택되는 제형을 갖는 피부 미백용 화장료 조성물.The cosmetic composition for skin whitening according to claim 6, wherein the cosmetic composition for skin whitening is an external ointment, cream, foam, lotion, pack, soft water, latex, foundation, makeup base, essence, soap, liquid cleanser, bath agent, sunscreen cream, and sun oil Cosmetic composition for skin whitening having a formulation selected from the group consisting of.
KR1020050024122A 2005-03-23 2005-03-23 Cosmetic composition for whitening of the skin having silanoyl oxymethyl-methyl imidazole derivatives KR20060102175A (en)

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