KR20210003827A - 미백제 - Google Patents
미백제 Download PDFInfo
- Publication number
- KR20210003827A KR20210003827A KR1020207033204A KR20207033204A KR20210003827A KR 20210003827 A KR20210003827 A KR 20210003827A KR 1020207033204 A KR1020207033204 A KR 1020207033204A KR 20207033204 A KR20207033204 A KR 20207033204A KR 20210003827 A KR20210003827 A KR 20210003827A
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- skin
- phenyl
- whitening
- aminomethylcyclohexylcarbonyl
- Prior art date
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- 230000002087 whitening effect Effects 0.000 title claims abstract description 65
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 31
- 239000002537 cosmetic Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 abstract description 4
- 210000003491 skin Anatomy 0.000 description 43
- -1 propioloyl group Chemical group 0.000 description 37
- 238000003756 stirring Methods 0.000 description 20
- 208000012641 Pigmentation disease Diseases 0.000 description 18
- 238000009472 formulation Methods 0.000 description 15
- 230000019612 pigmentation Effects 0.000 description 15
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
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- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 9
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- 102000003425 Tyrosinase Human genes 0.000 description 8
- 108060008724 Tyrosinase Proteins 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- 239000006210 lotion Substances 0.000 description 7
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- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
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- IETMVPCSNVEVLZ-UHFFFAOYSA-N 2-[4-[4-(aminomethyl)cyclohexanecarbonyl]phenyl]ethyl acetate Chemical compound C1=CC(CCOC(=O)C)=CC=C1C(=O)C1CCC(CN)CC1 IETMVPCSNVEVLZ-UHFFFAOYSA-N 0.000 description 2
- FUONDAIGKJKVJR-UHFFFAOYSA-N 2-[4-[4-(aminomethyl)cyclohexanecarbonyl]phenyl]ethyl propanoate Chemical compound C(CC)(=O)OCCC1=CC=C(C=C1)C(=O)C1CCC(CC1)CN FUONDAIGKJKVJR-UHFFFAOYSA-N 0.000 description 2
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Abstract
본 발명은, 뛰어난 미백 작용을 가지는 미백제를 제공하는 것을 과제로 한다. 하기 화학식 (1)로 나타나는 화합물 또는 그 산부가염을, 미백제의 유효성분으로 한다.
(식 중, X는 수소원자가 메틸기로 치환되어 있어도 좋은 탄소수 1~2의 알킬렌기를 나타내고, Y는 COOR1 또는 CH2OR2를 나타내며, R1은 수소원자 또는 분기를 가져도 좋은 탄소수 1~6의 알킬기를 나타내고, R2는 수소원자 또는 분기를 가져도 좋은 탄소수 1~6의 아실기를 나타냄.)
(식 중, X는 수소원자가 메틸기로 치환되어 있어도 좋은 탄소수 1~2의 알킬렌기를 나타내고, Y는 COOR1 또는 CH2OR2를 나타내며, R1은 수소원자 또는 분기를 가져도 좋은 탄소수 1~6의 알킬기를 나타내고, R2는 수소원자 또는 분기를 가져도 좋은 탄소수 1~6의 아실기를 나타냄.)
Description
본 발명은, 뛰어난 미백 작용을 가지는 미백제에 관한 것이다.
자외선 노출에 의한 그을림 이외에, 기미, 주근깨, 검버섯, 약제에 의한 피부의 흑화증 등의 색소침착에 따른 피부증상은, 색소세포(멜라노사이트)의 멜라닌 생성이 항진된 후, 생성된 멜라닌색소가 턴오버 이상 등에 의하여 피부에 침착함으로써 생기는 것이 알려져 있다.
이와 같은 색소침착이 관련된 피부증상은 외관으로부터 쉽게 보이므로, 얼굴의 인상에 크게 영향을 미친다. 그 때문에, 피부의 색소침착의 예방이나 개선에 대한 관심은, 피부를 아름답게 보이고 싶다는 소망을 가진 사람을 중심으로 매우 높아, 미백제나 미백용 화장료의 수요는 최근 커져 있다.
피부의 색소침착의 예방 또는 개선을 목적으로 하는 미백제로서는, 아스코르브산이나 히드로퀴논 등이 오래전부터 알려져 있고, 이들을 배합한 피부외용제가, 피부의 색소침착의 예방 또는 개선용으로 널리 사용되어 왔다. 또한, 최근, 색소침착이 생기는 작용기서의 해명에 의하여, 멜라닌 생성억제제, 티로시나아제 저해제, 티로시나아제 유전자발현 억제제, α-MSH 저해제, 항산화제, 멜라노사이트의 덴드라이트 신장억제제, 멜라노사이트의 케라티노사이트로의 멜라노솜 전달저해제 등의 종래의 미백제와는 다른 작용기서를 가지는 미백제의 개발도 활발하게 이루어지고 있다.
하지만, 종래의 미백제에서는 일정한 미백 효과가 인정되지만 충분히 만족할만한 것이 아닌 경우가 있거나, 미백 작용을 발휘하는 농도에서는 바람직하지 않은 다른 작용(부반응)이 발생하거나 하는 경우가 있다. 그 때문에, 안전성이 높고, 또한 뛰어난 미백 작용을 발휘하는 새로운 성분의 수요가 있어, 연구 개발이 진행되고 있다.
세트락세이트 또는 그 염 또한 최근 개발된 미백제의 유효성분의 하나이며, 대사에 의하여 트라넥삼산에 분해되는 화합물이다(특허문헌 1). 트라넥삼산은, 멜라노사이트를 활성화하는 프로스타글란딘 E2의 생성억제작용과, 티로시나아제 저해작용을 가지고, 미백 효과를 나타내는 것이 알려져 있다. 세트락세이트는 그 대사물인 트라넥삼산에 의한 미백 작용과 더불어, 화합물 자체의 활성에 의한 미백 작용도 가지는 것이 보고되어 있다.
그런데, 특허문헌 2에 기재된 아미노카르본산 유도체는, 항궤양 작용이 있는 것이 확인되어 있어, 의약품으로서의 용도가 제안되어 있다. 한편, 그러한 화합물의 구조는 트라넥삼산과 부분적으로 일치한다.
본 발명은, 안전성이 높고, 또한 뛰어난 미백 작용을 가지는 미백제를 제공하는 것을 과제로 한다.
본 발명자들은, 미백 작용을 가지는 화합물을 찾아 예의 연구를 거듭한 결과, 특정 구조를 가지는 아미노카르본산 유도체 및 그 산부가염이 뛰어난 미백 작용을 발휘하는 것을 발견하고, 본 발명을 완성시키기에 이르렀다.
즉, 본 발명의 일 실시형태는, 하기 화학식 (1)로 나타나는 화합물 또는 그 산부가염을 함유하는 미백제이다.
[화학식 1]
(식 중, X는 수소원자가 메틸기로 치환되어 있어도 좋은 탄소수 1~2의 알킬렌기를 나타내고, Y는 COOR1 또는 CH2OR2를 나타내며, R1은 수소원자 또는 분기를 가져도 좋은 탄소수 1~6의 알킬기를 나타내고, R2는 수소원자 또는 분기를 가져도 좋은 탄소수 1~6의 아실기를 나타냄.)
또한, 본 발명의 다른 실시형태는, 상기 미백제를 함유하는 미백용 피부외용 조성물이다. 상기 피부외용 조성물은, 바람직하게는 화장료이다.
본 발명에 의하여, 뛰어난 미백 작용을 가지는 미백제가 제공된다. 또한, 그 미백제를 함유하는, 미백용 피부외용 조성물도 제공되며, 이것은 화장료로서 적합하다.
본 발명의 미백제는, 하기 화학식 (1)로 나타나는 화합물 또는 그 산부가염을 함유한다.
[화학식 2]
화학식 (1) 중, X는, 수소원자가 메틸기로 치환되어 있어도 좋은 탄소수 1~2의 알킬렌기를 나타낸다. 탄소수 1~2의 알킬렌기로서는, 메틸렌기, 및 에틸렌기이다. X는 -CH2-CH(CH3)-, 또는 -CH2-CH2-가 바람직하다.
화학식 (1) 중, Y는, COOR1 또는 CH2OR2를 나타내며, R1은 수소원자 또는 분기를 가져도 좋은 탄소수 1~6의 알킬기를 나타내고, R2는 수소원자 또는 분기를 가져도 좋은 탄소수 1~6의 아실기를 나타낸다.
즉, Y가 COOR1인 경우, R1이 수소원자일 때 Y는 카르복실기이고, R1이 분기를 가져도 좋은 탄소수 1~6의 알킬기일 때 Y는 에스테르기이다. 분기를 가져도 좋은 탄소수 1~6의 알킬기로서는, 예를 들어, 메틸기, 에틸기, n-프로필기, iso-프로필기, n-부틸기, iso-부틸기, tert-부틸기, n-펜틸기, n-헥실기 등을 들 수 있다. 미백 작용의 관점에서, R1은 수소원자인 것이 특히 바람직하고, 또한 R1이 알킬기일 때에는 그 탄소수는 작은 편이 보다 바람직하다.
또한, Y가 CH2OR2인 경우, R2가 수소원자일 때 Y는 히드록시메틸기이고, R2가 분기를 가져도 좋은 탄소수 1~6의 아실기일 때 Y는 에스테르기이다. 분기를 가져도 좋은 탄소수 1~6의 아실기로서는, 예를 들어, 포밀기, 아세틸기, 아크릴로일기, 프로피오닐기, 프로피올로일기, 부티릴기, 이소부티릴기, 메타크릴로일기, 발레릴기, 카프로일기 등을 들 수 있다. 미백 작용의 관점에서, R2는 수소원자인 것이 특히 바람직하고, 또한 R2가 아실기일 때에는 그 탄소수는 작은 편이 보다 바람직하다.
화학식 (1)에 있어서, 1,4-시클로헥실렌기는, 의자형 또는 보트형 중 어느 형태여도 좋다. 또한, 2개의 결합은, 시스 또는 트랜스 중 어느 관계여도 좋다. 바람직하게는, 의자형의 형태로 트랜스의 관계에 있는 것이다.
하기 화학식 (1)로 나타나는 화합물의 산부가염으로서는, 무기산, 유기카르본산, 또는 유기술폰산과의 염을 들 수 있다. 무기산으로서는, 염산, 취화수소산, 황산, 질산, 인산 등을 들 수 있고, 유기카르본산으로서는, 초산, 프로피온산, 말레인산, 푸말산, 옥살산, 구연산, 낙산, 유산, 주석산 등을 들 수 있으며, 유기술폰산으로서는, 메탄술폰산, 에탄술폰산, 벤젠술폰산, 파라톨루엔술폰산 등을 들 수 있다. 이들 중 무기산염이 바람직하고, 염산염이 보다 바람직하다.
본 발명의 미백제의 유효성분으로서는, 화학식 (1)로 나타나는 화합물 또는 그 산부가염 중 어느 것이어도 좋은데, 산부가염이 보다 바람직하다.
화학식 (1)로 나타나는 화합물의 구체예를 이하에 열거하는데, 이들로만 한정되지 않는 것은 말할 것도 없다.
2-[p-(4-아미노메틸시클로헥실카르보닐)페닐］초산, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]초산메틸, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]초산에틸, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]초산프로필, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]초산부틸, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]초산펜틸, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]초산헥실;
2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]에탄올, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]에틸포르메이트, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]에틸아세테이트, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]에틸프로피오네이트, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]에틸부틸레이트, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]에틸펜타노에이트, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]에틸헥사노에이트;
2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로피온산, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로피온산메틸, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로피온산에틸, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로피온산프로필, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로피온산부틸, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로피온산펜틸, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로피온산헥실;
2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로판올, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필포르메이트, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필아세테이트, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필프로피오네이트, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필부틸레이트, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필펜타노에이트, 2-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필헥사노에이트;
3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로피온산(화합물 1), 3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로피온산메틸, 3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로피온산에틸, 3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로피온산프로필, 3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로피온산부틸, 3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로피온산펜틸, 3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로피온산헥실(화합물 2);
3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로판올(화합물 3), 3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필포르메이트, 3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필아세테이트, 3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필프로피오네이트, 3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필부틸레이트, 3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필펜타노에이트, 3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필헥사노에이트(화합물 4);
2-메틸-3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로판올, 2-메틸-3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필포르메이트, 2-메틸-3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필아세테이트, 2-메틸-3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필프로피오네이트, 2-메틸-3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필부틸레이트, 2-메틸-3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필펜타노에이트, 2-메틸-3-[p-(4-아미노메틸시클로헥실카르보닐)페닐]프로필헥사노에이트(화합물 5).
[화학식 3]
[화학식 4]
[화학식 5]
[화학식 6]
[화학식 7]
화학식 (1)로 나타나는 화합물은, 정법에 의하여 합성·정제하여 취득할 수 있다. 예를 들어, 특허문헌 2에 기재된, 아미노카르본산할라이드의 산부가염의 루이스산 존재 하에서의 아실화 반응에 의하여 합성하고, 적당한 단리·정제 방법을 거쳐 제조할 수 있다.
화학식 (1)로 나타나는 화합물 및 그 산부가염은, 뛰어난 미백 작용을 가지므로, 미백제의 유효성분이 된다.
한편, 본 명세서에 있어서 미백이란, 색소침착의 예방 및/또는 개선을 말하며, 보다 구체적으로는, 기미, 칙칙함, 주근깨, 그을림, 피부의 염증이나 자극에 의한 거무스름 등의 멜라닌 생성항진, 과잉축적, 및 침착이상 등에 의하여 생기는 색소침착증상, 그리고 스테로이드 등의 약물에 의한 피부의 흑화증 등의 색소침착을 초래하는 질환 등에 의한 색소침착증상 등의, 예방 및/또는 개선을 말한다.
본 발명의 미백제의 작용기서에 대하여는, 상세하게는 불분명하지만, 티로시나아제 저해작용, 티로시나아제 유전자발현 억제작용, 티로시나아제 단백발현 억제작용, 티로시나아제 관련단백 분해작용 등의 티로시나아제 활성저해작용, 프로톤 펌프 저해작용, 멜라노사이트의 케라티노사이트로의 멜라노솜 전달저해작용, 또는 새로운 작용기서에 의하여, 색소침착을 예방 및/또는 개선하는 것이 추측된다.
본 발명은, 다른 측면에서, 화학식 (1)로 나타나는 화합물 또는 그 산부가염을 적용하는 것을 포함하는, 미백방법 또는 색소침착의 예방 및/또는 개선방법이라고도 할 수 있다.
본 발명은, 다른 측면에서, 화학식 (1)로 나타나는 화합물 또는 그 산부가염의, 미백을 위한 또는 색소침착의 예방 및/또는 개선을 위한 사용이라고도 할 수 있다.
본 발명은, 다른 측면에서, 화학식 (1)로 나타나는 화합물 또는 그 산부가염의, 미백제의 제조에 있어서의 사용이라고도 할 수 있다.
본 발명은, 다른 측면에서, 미백 또는 색소침착의 예방 및/또는 개선을 위하여 사용되는 화학식 (1)로 나타나는 화합물 또는 그 산부가염이라고도 할 수 있다.
화학식 (1)로 나타나는 화합물의 구조는, 트라넥삼산과 부분적으로 일치하는데, 생체 내에서 트라넥삼산에는 대사되지 않는 것을 알고 있다. 즉, 화학식 (1)로 나타나는 화합물의 미백 작용은, 트라넥삼산과는 다른 메커니즘에 의한 것으로 생각되며, 적어도 (4-아미노메틸시클로헥실카르보닐)페닐기의 구조가 그 작용의 발휘에 관여하는 것으로 추측된다.
한편, 특허문헌 1에 기재된 세트락세이트는, 트라넥삼산의 에스테르 유도체이고, 그 자체의 구조에 의하여, 및 대사에 의하여 에스테르 결합이 절단되어 트라넥삼산이 되는 것에 의하여 미백 작용을 발휘한다.
[화학식 8]
[화학식 9]
본 발명의 미백제는, 미백용 조성물에 함유시킬 수 있고, 특히 경피흡수에 의한 효과가 기대 가능한 피부외용 조성물로 하는 것이 바람직하다. 피부외용 조성물의 실시형태로서는, 피부에 외용으로 적용되는 것이라면 특별히 한정되지 않지만, 화장료(의약부외품을 포함함), 의약품 등을 바람직하게 들 수 있다. 화학식 (1)로 나타나는 화합물은, 높은 안전성이 확인되어 있으며, 일상적으로 사용되는 화장료의 형태로 연속적으로 도포하는 것이 가능하다.
피부외용 조성물의 제형으로서는, 특별히 한정되지 않으며, 예를 들어, 로션제형, 유액이나 크림 등의 유화제형, 오일제형, 젤제형, 팩, 세정료 등을 들 수 있다.
본 발명의 미백제를 미백용 피부외용 조성물에 함유시키는 경우에는, 그 양을 조성물 전량에 대하여 총량으로, 바람직하게는 0.01％~20질량％, 보다 바람직하게는 0.1~10질량％, 더욱 바람직하게는 1~5질량％의 함유량으로 하면, 원하는 효과를 얻기 쉽고, 또한 처방설계의 자유도를 확보할 수 있다.
본 발명의 미백용 피부외용 조성물은, 본 발명의 미백제 이외에 통상의 피부외용 조성물에 배합되는 성분을, 본 발명의 효과를 손상하지 않는 한에 있어서 임의로 함유할 수 있다.
이러한 성분으로서는, 예를 들어, 마카데미아너츠유, 아보카도유, 옥수수유, 올리브유, 유채유, 참기름, 피마자유, 새플라워유, 면실유, 호호바유, 야자유, 팜유, 액상라놀린, 경화야자유, 경화유, 목랍, 경화피마자유, 밀납, 칸데리라납, 카르나우바납, 백랍, 라놀린, 환원라놀린, 경질라놀린, 호호바납 등의 오일, 왁스류; 유동파라핀, 스쿠알렌, 프리스탄, 오조케라이트, 파라핀, 세레신, 바셀린, 마이크로크리스탈린왁스 등의 탄화수소류; 올레인산, 이소스테아린산, 라우린산, 미리스틴산, 팔미틴산, 스테아린산, 베헨산, 운데실렌산 등의 고급지방산류; 세틸알코올, 스테아릴알코올, 이소스테아릴알코올, 베헤닐알코올, 옥틸도데칸올, 미리스틸알코올, 세토스테아릴알코올 등의 고급알코올 등; 이소옥탄산세틸, 미리스틴산이소프로필, 이소스테아린산헥실데실, 아디프산디이소프로필, 세바신산디-2-에틸헥실, 유산세틸, 사과산디이소스테아릴, 디-2-에틸헥산산에틸렌글리콜, 디카프린산네오펜틸글리콜, 디-2-헵틸운데칸산글리세린, 트리-2-에틸헥산산글리세린, 트리-2-에틸헥산산트리메틸롤프로판, 트리이소스테아린산트리메틸롤프로판, 테트라-2-에틸헥산산펜타에리트리트 등의 합성에스테르유류; 디메틸폴리실록산, 메틸페닐폴리실록산, 디페닐폴리실록산 등의 쇄상 폴리실록산; 옥타메틸시클로테트라실록산, 데카메틸시클로펜타실록산, 도데카메틸시클로헥사실록산 등의 환상 폴리실록산; 아미노변성폴리실록산, 폴리에테르변성폴리실록산, 알킬변성폴리실록산, 불소변성폴리실록산 등의 변성폴리실록산 등의 실리콘유 등의 유제류;
지방산비누(라우린산나트륨, 팔미틴산나트륨 등), 라우릴황산칼륨, 알킬황산트리에탄올아민에테르 등의 음이온 계면활성제류; 염화스테아릴트리메틸암모늄, 염화벤잘코늄, 라우릴아민옥사이드 등의 양이온 계면활성제류; 이미다졸린계 양성 계면활성제(2-코코일-2-이미다졸리늄히드록사이드-1-카르복시에틸옥시2나트륨염 등), 베타인계 계면활성제(알킬베타인, 아미드베타인, 술포베타인 등), 아실메틸타우린 등의 양성 계면활성제류; 소르비탄지방산에스테르류(소르비탄모노스테아레이트, 세스키올레인산소르비탄 등), 글리세린지방산류(모노스테아린산글리세린 등), 프로필렌글리콜지방산에스테르류(모노스테아린산프로필렌글리콜 등), 경화피마자유유도체, 글리세린알킬에테르, POE소르비탄지방산에스테르류(POE소르비탄모노올레에이트, 모노스테아린산폴리옥시에틸렌소르비탄 등), POE소르비트지방산에스테르류(POE-소르비트모노라우레이트 등), POE글리세린지방산에스테르류(POE-글리세린모노이소스테아레이트 등), POE지방산에스테르류(폴리에틸렌글리콜모노올레이트, POE디스테아레이트 등), POE알킬에테르류(POE2-옥틸도데실에테르 등), POE알킬페닐에테르류(POE노닐페닐에테르 등), 플루로닉형류, POE·POP알킬에테르류(POE·POP2-데실테트라데실에테르 등), 테트로닉류, POE피마자유·경화피마자유유도체(POE피마자유, POE경화피마자유 등), 자당지방산에스테르, 알킬글루코시드 등의 비이온 계면활성제류; 폴리에틸렌글리콜, 글리세린, 1,3-부틸렌글리콜, 에리스리톨, 소르비톨, 크실리톨, 말티톨, 프로필렌글리콜, 디프로필렌글리콜, 디글리세린, 이소프렌글리콜, 1,2-펜탄디올, 2,4-헥산디올, 1,2-헥산디올, 1,2-옥탄디올 등의 다가알코올류;
피롤리돈카르본산나트륨, 유산, 유산나트륨 등의 보습성분류; 표면이 처리되어 있어도 좋은, 마이카, 탈크, 카올린, 합성운모, 탄산칼슘, 탄산마그네슘, 무수규산(실리카), 산화알루미늄, 황산바륨 등의 분체류; 표면이 처리되어 있어도 좋은, 벵갈라, 황산화철, 흑산화철, 산화코발트, 군청, 감청, 산화티탄, 산화아연의 무기안료류; 표면이 처리되어 있어도 좋은, 운모티탄, 어린박, 옥시염화비스무트 등의 펄제류; 레이크화되어 있어도 좋은 적색202호, 적색228호, 적색226호, 황색4호, 청색404호, 황색5호, 적색505호, 적색230호, 적색223호, 등색201호, 적색213호, 황색204호, 황색203호, 청색1호, 녹색201호, 자색201호, 적색204호 등의 유기색소류; 폴리에틸렌분말, 폴리메타크릴산메틸, 나일론분말, 올가노폴리실록산엘라스토머 등의 유기분체류; 파라아미노안식향산계 자외선흡수제; 안트라닐산계 자외선흡수제; 살리칠산계 자외선흡수제; 계피산계 자외선흡수제; 벤조페논계 자외선흡수제; 당계 자외선흡수제; 2-(2'-히드록시-5'-t-옥틸페닐)벤조트리아졸, 4-메톡시-4'-t-부틸디벤조일메탄 등의 자외선흡수제류;
에탄올, 이소프로판올 등의 저급알코올류; 비타민 A 또는 그 유도체, 비타민 B6 염산염, 비타민 B6 트리팔미테이트, 비타민 B6 디옥타노에이트, 비타민 B2 또는 그 유도체, 비타민 B12, 비타민 B15 또는 그 유도체 등의 비타민 B류; α-토코페롤, β-토코페롤, γ-토코페롤, 비타민 E 아세테이트 등의 비타민 E류, 비타민 D류, 비타민 H, 판토텐산, 판테틴, 피로로퀴놀린퀴논 등의 비타민류 등; 메틸파라벤, 에틸파라벤, 부틸파라벤, 페녹시에탄올 등의 항균제(방부제); 글리틸리틴산 유도체, 글리틸레틴산 유도체, 살리칠산 유도체, 히노키티올, 산화아연, 알라토인 등의 소염제; 레티놀, 아스코르브산, 토코페롤, 또는 파르네실초산에스테르 등의 주름 개선제; 각종 추출물(예를 들어, 황벽, 황련, 자근, 작약, 쓴풀, 버치, 세이지, 비파, 당근, 알로에, 당아욱, 아이리스, 포도, 의이인, 수세미, 백합, 사프란, 천궁이, 생강, 물레나물, 오노니스, 마늘, 고추, 진피, 당귀, 해조 등); 로열젤리, 감광소, 콜레스테롤 유도체 등의 부활제; 노닐산발레닐아미드, 캅사이신, 진저론, 탄닌산 등의 혈행촉진제; 유황, 티안톨 등의 항지루제; 트라넥삼산, 티오타우린, 히포타우린 등의 항염증제; 콜라겐, 히아루론산 등의 수용성고분자; 등을 들 수 있다.
또한, 본 발명의 미백제 이외의 미백제를 함께 배합하여도 상관없다. 예를 들어, 알킬레조르시놀, 아스코르브산 또는 그 유도체, 태반추출물, 범의귀나 율무 등의 식물추출물, 알부틴 등을 들 수 있다.
실시예
이하, 구체적인 실험예를 들어, 본 발명을 더욱 상세하게 설명하는데, 본 발명은 이하의 실시형태만으로 한정되지 않는다.
<미백 효과의 시험>
표 1에 기재된 화장료(실시예 1~9, 비교예, 및 참고예)를 각각 정법으로 조제하였다.
조제한 각 화장료에 대하여, 이하의 방법으로 미백 효과(색소침착의 개선 효과)를 평가하였다. 즉, 자유의사로 참가한 패널 10명이 좌우 상완 내측부에 0.5cmХ0.5cm의 시험부위를 합계 8군데 설정하였다. 설정한 부위에 최소홍반량(1MED)의 자외선 조사를 1일 1회, 3일 연속하여 3회 조사하였다. 시험 1일째의 자외선 조사 종료시(1회째 조사 종료 후)로부터, 1일 2회 25일 연속하여 비교예와 나머지 7군데에 실시예 1~9 및 참고예의 어느 화장료를 각 50μL 도포하였다. 25일간의 도포 종료 24시간 후에 색채색차계(CR-300, 코니카미놀타 주식회사)로 각 시험부위의 피부명도(L*값)를 측정하고, 실시예 또는 참고예의 화장료의 도포 부위의 L*값으로부터 비교예의 화장료의 도포 부위의 L*값을 빼서 피부 명도의 차이(△L*값)를 산출하였다. L*값은, 색소침착의 정도가 강할수록 낮은 값이 되므로, △L*값이 클수록, 색소침착이 개선되었다고 판단할 수 있다.
[표 1]
[표 2]
<제조예 1>
표 3에 나타내는 처방으로, 본 발명의 피부외용제인 화장수를 조제하였다. 즉, A의 성분을 상온에서, B의 성분을 60℃에서 각각 가온하여 혼합하고, 교반 하에서 A에 B를 서서히 첨가하여, 교반 냉각하여서 화장수를 얻었다.
이러한 화장수는 피부에 적용하였을 때에 미백 효과가 얻어지는 것이 확인되었다.
[표 3]
<제조예 2>
표 4에 나타내는 처방으로, 본 발명의 피부외용제인 화장수를 조제하였다. 즉, A의 성분을 상온에서, B의 성분을 60℃에서 각각 가온하여 혼합하고, 교반 하에서 A에 B를 서서히 첨가하여, 교반 냉각하여서 화장수를 얻었다.
이러한 화장수는 피부에 적용하였을 때에 미백 효과가 얻어지는 것이 확인되었다.
[표 4]
<제조예 3>
표 5에 나타내는 처방으로, 본 발명의 피부외용제인 에센스를 조제하였다. 즉, A 및 B의 성분을 80℃에서 각각 가온하여 혼합하고, 교반 하에서 A에 B를 서서히 첨가하여, 교반 냉각하여서 에센스를 얻었다.
이러한 에센스는 피부에 적용하였을 때에 미백 효과가 얻어지는 것이 확인되었다.
[표 5]
<제조예 4>
표 6에 나타내는 처방으로, 본 발명의 피부외용제인 유액을 조제하였다. 즉, A 및 B의 성분을 80℃에서 각각 가온하여 혼합하고, 교반 하에서 A에 B를 서서히 첨가하여, 교반 냉각하여서 유액을 얻었다.
이러한 유액은 피부에 적용하였을 때에 미백 효과가 얻어지는 것이 확인되었다.
[표 6]
<제조예 5>
표 7에 나타내는 처방으로, 본 발명의 피부외용제인 O/W 크림을 조제하였다. 즉, A 및 B의 성분을 80℃에서 각각 가온하여 혼합하고, 교반 하에서 A에 B를 서서히 첨가하여, 교반 냉각하여서 O/W 크림을 얻었다.
이러한 O/W 크림은 피부에 적용하였을 때에 미백 효과가 얻어지는 것이 확인되었다.
[표 7]
<제조예 6>
표 8에 나타내는 처방으로, 본 발명의 피부외용제인 W/O 크림을 조제하였다. 즉, A 및 B의 성분을 80℃에서 각각 가온하여 혼합하고, 교반 하에서 B에 A를 서서히 첨가하여, 교반 냉각하여서 W/O 크림을 얻었다.
이러한 W/O 크림은 피부에 적용하였을 때에 미백 효과가 얻어지는 것이 확인되었다.
[표 8]
<제조예 7>
표 9에 나타내는 처방으로, 본 발명의 피부외용제인 O/W 파운데이션을 조제하였다. 즉, A 및 B의 성분을 80℃에서 각각 가온하여 혼합하고, 교반 하에서 A에 B를 서서히 첨가하여, 교반 냉각하여서 O/W 파운데이션을 얻었다.
이러한 O/W 파운데이션은 피부에 적용하였을 때에 미백 효과가 얻어지는 것이 확인되었다.
[표 9]
<제조예 8>
표 10에 나타내는 처방으로, 본 발명의 피부외용제인 W/O 파운데이션을 조제하였다. 즉, A 및 B의 성분을 80℃에서 각각 가온하여 혼합하고, 교반 하에서 B에 A를 서서히 첨가하여, 교반 냉각하여서 W/O 파운데이션을 얻었다.
이러한 W/O 파운데이션은 피부에 적용하였을 때에 미백 효과가 얻어지는 것이 확인되었다.
[표 10]
<제조예 9>
표 11에 나타내는 처방으로, 본 발명의 피부외용제인 O/W 자외선차단제를 조제하였다. 즉, A 및 B의 성분을 80℃에서 각각 가온하여 혼합하고, 교반 하에서 A에 B를 서서히 첨가하여, 교반 냉각하여서 O/W 자외선차단제를 얻었다.
이러한 O/W 자외선차단제는 피부에 적용하였을 때에 미백 효과가 얻어지는 것이 확인되었다.
[표 11]
<제조예 10>
표 12에 나타내는 처방으로, 본 발명의 피부외용제인 W/O 자외선차단제를 조제하였다. 즉, A 및 B의 성분을 80℃에서 각각 가온하여 혼합하고, 교반 하에서 B에 A를 서서히 첨가하여, 교반 냉각하여서 W/O 자외선차단제를 얻었다.
이러한 W/O 자외선차단제는 피부에 적용하였을 때에 미백 효과가 얻어지는 것이 확인되었다.
[표 12]
본 발명의 미백제는, 뛰어난 미백 효과를 나타내므로, 미백용 피부외용 조성물에 적합하게 함유시킬 수 있어, 산업상 매우 유용하다.
Claims (3)
- 하기 화학식 (1)로 나타나는 화합물 또는 그 산부가염을 함유하는 미백제.
[화학식 1]
(식 중, X는 수소원자가 메틸기로 치환되어 있어도 좋은 탄소수 1~2의 알킬렌기를 나타내고, Y는 COOR1 또는 CH2OR2를 나타내며, R1은 수소원자 또는 분기를 가져도 좋은 탄소수 1~6의 알킬기를 나타내고, R2는 수소원자 또는 분기를 가져도 좋은 탄소수 1~6의 아실기를 나타냄.) - 제 1 항에 기재된 미백제를 함유하는 미백용 피부외용 조성물.
- 제 2 항에 있어서,
화장료인 피부외용 조성물.
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| JPJP-P-2018-101963 | 2018-05-29 | ||
| PCT/JP2019/017350 WO2019230274A1 (ja) | 2018-05-29 | 2019-04-24 | 美白剤 |
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| JP5462504B2 (ja) * | 2008-03-21 | 2014-04-02 | 第一三共ヘルスケア株式会社 | 美白用組成物 |
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| JP2008110967A (ja) | 2006-10-02 | 2008-05-15 | Daiichi Sankyo Healthcare Co Ltd | セトラキサートを含有する美白剤 |
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| JPWO2019230274A1 (ja) | 2021-06-17 |
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| CN112135599B (zh) | 2023-03-31 |
| AU2019278251A1 (en) | 2020-12-10 |
| EP3804690B1 (en) | 2024-06-05 |
| AU2019278251B2 (en) | 2021-12-16 |
| EP3804690A1 (en) | 2021-04-14 |
| EP3804690A4 (en) | 2022-06-08 |
| BR112020023802A2 (pt) | 2021-02-23 |
| RU2757906C1 (ru) | 2021-10-22 |
| WO2019230274A1 (ja) | 2019-12-05 |
| US20210196599A1 (en) | 2021-07-01 |
| BR112020023802B1 (pt) | 2023-10-31 |
| MX2020012483A (es) | 2021-02-15 |
| CA3101313C (en) | 2023-01-24 |
| SG11202011525WA (en) | 2020-12-30 |
| IL278816B2 (en) | 2023-11-01 |
| TW202015653A (zh) | 2020-05-01 |
| CA3101313A1 (en) | 2019-12-05 |
| JP7239573B2 (ja) | 2023-03-14 |
| NZ770176A (en) | 2024-02-23 |
| KR102513180B1 (ko) | 2023-03-23 |
| UA126100C2 (uk) | 2022-08-10 |
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