WO2013047923A1 - Nanoemulsion containing a polyaspartic acid derivative and personal care composition containing same - Google Patents

Nanoemulsion containing a polyaspartic acid derivative and personal care composition containing same Download PDF

Info

Publication number
WO2013047923A1
WO2013047923A1 PCT/KR2011/007162 KR2011007162W WO2013047923A1 WO 2013047923 A1 WO2013047923 A1 WO 2013047923A1 KR 2011007162 W KR2011007162 W KR 2011007162W WO 2013047923 A1 WO2013047923 A1 WO 2013047923A1
Authority
WO
WIPO (PCT)
Prior art keywords
nanoemulsion
weight
parts
lysine
present
Prior art date
Application number
PCT/KR2011/007162
Other languages
French (fr)
Korean (ko)
Inventor
박선기
오선택
이종길
지홍근
유효경
전봉주
Original Assignee
주식회사 코스메카코리아
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 주식회사 코스메카코리아 filed Critical 주식회사 코스메카코리아
Priority to PCT/KR2011/007162 priority Critical patent/WO2013047923A1/en
Publication of WO2013047923A1 publication Critical patent/WO2013047923A1/en

Links

Images

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/74—Synthetic polymeric materials
    • A61K31/785—Polymers containing nitrogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • 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
    • A61K8/55—Phosphorus compounds
    • A61K8/553—Phospholipids, e.g. lecithin
    • 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
    • A61K8/60—Sugars; Derivatives 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
    • A61K8/72—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
    • A61K8/88—Polyamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • 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
    • 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
    • A61K2800/70—Biological properties of the composition as a whole
    • A61K2800/72—Hypo-allergenic

Definitions

  • the present invention relates to nanoparticles comprising 1 to 20 parts by weight of polyaspartic acid derivatives, 1 to 5 parts by weight of saturated lecithin, 1 to 10 parts by weight of dissolution aid, 0.1 to 5 parts by weight of resorcithin and 1 to 5 parts by weight of sucrose fatty acid ester surfactant.
  • Emulsion, and a personal care composition comprising the same
  • the personal care composition comprising the nanoemulsion of the present invention can induce collagen biosynthesis and is very excellent in inhibiting matrix metalloproteinase-1 (MMP-1) and anti-allergic effect.
  • MMP-1 matrix metalloproteinase-1
  • the polymers currently applied in the cosmetic field include polyacrylates and polyvinyls, polyethylene glycol (PEG) of various molecular weights, polysorbates, polysaccharides, polysilicones, polyamino acids and various polypeptides. Except for the moisturizing effect, it is only used as a thickener, a feeling-improving agent, an emulsifier, etc., which serve as a basic framework of cosmetic formulations rather than an efficacy aspect.
  • PEG polyethylene glycol
  • the present invention can solve the problem of transdermal absorption of polymer materials while improving the physiological efficacy, especially skin activity, using polyamino acid-based materials which are highly reactive, applicable, biocompatible and environmentally friendly materials among various biopolymers. It is a technical task to provide a solution.
  • a nanoemulsion comprising 1 to 20 parts by weight of a polyaspartic acid derivative, 1 to 5 parts by weight of saturated lecithin, 1 to 10 parts by weight of dissolution aid, 0.1 to 5 parts by weight of resorcithin and 1 to 5 parts by weight of sucrose fatty acid ester surfactant.
  • the nanoemulsion of the present invention can be rapidly absorbed into the skin, induce collagen biosynthesis, inhibit wrinkles by inhibiting matrix metalloproteinase-1 (MMP-1), and have an excellent antiallergic effect.
  • MMP-1 matrix metalloproteinase-1
  • FIG. 2 is an enlarged photograph of the nanoemulsion of the present invention using a frozen electron microscope.
  • Figure 3 is a graph showing the results of measuring collagen biosynthesis effect.
  • PASP polyaspartic acid
  • PASP-Lysine polyaspartic acid derivative substituted with lysine
  • PASP-HDA-Lysine polyaspartic acid derivative substituted with lysine and hexadecylamine
  • TGF transforming growth factor
  • PASP-Lysine polyaspartic acid derivative substituted with lysine
  • PASP-HDA-Lysine polyaspartic acid derivative substituted with lysine and hexadecylamine
  • 5 is a micrograph taken of mast cells to examine the anti-allergic effect.
  • the present invention provides 1 to 20 parts by weight of a polyaspartic acid derivative, 1 to 5 parts by weight of saturated lecithin, 1 to 10 parts by weight of dissolution aid, 0.1 to 5 parts by weight of resorcinin and sucrose fatty acid ester surfactant. It provides a nanoemulsion comprising 5 parts by weight.
  • composition comprising the nanoemulsion of the present invention.
  • a nanoemulsion comprising a moiety.
  • Aspartic acid is an acidic amino acid that forms the protein of plants and animals. It is obtained from sugarcane, sugar beet, and molasses. It protects the immune system and brain and nerves, enhances vitality and energy, improves RNA / DNA function, and excessive ammonia and blood flow. Toxins are involved in the metabolism of other amino acids and biochemicals. Polyaspartic acid is a biocompatible and environmentally friendly material that is used as a material for medical drugs such as drug delievery system (DDS) of medicines, medical sutures, artificial skin, etc. Or it is broken down into monomers and absorbed through metabolism by cells or organs, which has been reported to affect wound healing and restoration of damaged tissues.
  • DDS drug delievery system
  • the polyaspartic acid derivative is synthesized polysuccinimide (PSI) by condensation polymerization under an acid catalyst using L-aspartic acid, and hydrolyzed and acidified to prepare polyaspartic acid followed by lysine, or
  • PSI polysuccinimide
  • the polyaspartic acid derivative is prepared by simultaneously combining lysine, or lysine and alkylamine, to one or more residues of polyaspartic acid according to the following FIG. 6 (Scheme 1).
  • R is —OH or C 10-20 alkylamine, such as n is from 20 to 1,000 and m is from 20 to 1500.
  • C 10-20 alkylamine is, for example, decylamine, dodecylamine, dodecylamine, pentadecylamine, hexadecylamine, heptadecylamine, heptadecylamine, octadecyl, octadecyl Alkylamines such as amines (octadecylamine) may be used, but are not limited thereto.
  • Lysine one of the amino acids, is not only easily lacked by Asians, especially grains, but is also reported to be an essential amino acid that is needed more in the growth phase of the human body, but is known to be involved in growth factors. It is not known much about its function because it is used in combination with various amino acids, it is included in almost all protein structures, especially histones, albumin, muscle protein and the like.
  • the polyasphatic acid derivative is preferably a polymer having a molecular weight of about 5,000 to 200,000, thereby solving the problem of transdermal absorption and introducing nanoemulsion technology for maximizing skin activity.
  • the nanoemulsion is 1 to 20 parts by weight of polyaspartic acid derivative, 1 to 5 parts by weight of saturated lecithin, 1 to 10 parts by weight of dissolution aid, 0.1 to 5 parts by weight of resorcinin and 1 to 5 parts by weight of sucrose fatty acid ester surfactant. It can be prepared by adding a residual amount of water, for example, 55 to 95.9 parts by weight of water and then mixing.
  • the nanoemulsion of the present invention contains 1 to 5 parts by weight, preferably 1.2 to 4 parts by weight, more preferably 1.5 to 3 parts by weight of saturated lecithin.
  • saturated lecithin forms a membrane of nanoemulsion
  • lecithin is a substance present in animal tissue and has excellent affinity with skin.
  • lecithin refers to a mixture of various phospholipids, and the composition of phospholipids may vary depending on their origin.
  • Saturated lecithin can be prepared by hydrogenating lecithin to convert all double bonds in the hydrocarbon chain of fatty acids into single bonds. Saturated lecithin is excellent in its white color and can be particularly preferably used in cosmetic applications.
  • the nanoemulsion of the present invention contains 1 to 10 parts by weight, preferably 2 to 8 parts by weight of the dissolution aid.
  • the dissolution aid in the present invention serves to help dissolution of the polyaspartic acid derivative, preferably ethanol.
  • the effect of assisting the dissolution of the polyaspartic acid derivative may be weakened, and when included in excess of 10 parts by weight, the emulsion stability may be lowered.
  • the nanoemulsion of the present invention contains 0.1 to 5 parts by weight, preferably 0.5 to 4 parts by weight of lysolecithin. Resorcinin in the present invention, together with saturated lecithin, makes the interfacial film of the nanoemulsion more robust.
  • the effect of the resorcithin may be weakened when the nanoemulsion is formed, and when included in excess of 5 parts by weight, the nanoemulsion may become unstable.
  • the nanoemulsion of the present invention contains 1 to 5 parts by weight, preferably 2 to 4 parts by weight of a sucrose fatty acid ester surfactant.
  • Sucrose fatty acid ester surfactants in the present invention form a film of nanoemulsion.
  • Sucrose fatty acid ester surfactant in the present invention for example, sucrose stearic acid ester, sucrose palmitate ester, sucrose myristic acid ester, sucrose oleic acid ester and sucrose lauric acid ester may be used, but is not limited thereto.
  • sucrose fatty acid ester surfactant is included in less than 1 part by weight in the present invention may be a problem in the formation of the nanoemulsion and if it is included in excess of 5 parts by weight as the amount of components contained in the emulsion due to the excess of the membrane component is reduced There may be a problem that the effect of the nanoemulsion of the present invention becomes insufficient.
  • the nanoemulsion in the present invention can be made by a variety of methods known in the art and there is no particular limitation thereto.
  • the nanoemulsion has a particle diameter of preferably about 50 to 200 nm. When the particle diameter of the nanoemulsion is about 50 to 200 nm, penetration into the skin may be facilitated.
  • a personal care composition comprising the nanoemulsion of the invention.
  • the personal care composition means a skin care composition, a body care composition, a hair care composition, and the like, and specific examples thereof include, but are not limited to, body lotion, shampoo, rinse, cream, lotion, essence, skin, and the like.
  • the personal care composition of the present invention preferably comprises 1 to 10% by weight, more preferably 2 to 8% by weight of the nanoemulsion according to the invention.
  • the effect provided by the nanoemulsion may be insignificant, and even if it contains more than 10% by weight, the effect provided by the nanoemulsion is in proportion to the addition thereof. It is hard to expect any more growth and is not economically desirable.
  • Polysuccinimide (PSI) was synthesized using L-aspartic acid as a catalyst under phosphoric acid at 180 ° C.
  • the synthesized PSI was hydrolyzed with 0.1N NaOH and acidified with 0.1N HCl to prepare poly (aspartic acid) (PASP), followed by N, N′-dicyclohexyl carbodiimide (N, N'-dicyclohexyl carbodiimide (DCC) was used as a coupling agent to react with L-lysine for 24 hours at 60 ° C. in a DMF solvent to obtain a polyaspartic acid derivative having a residue substituted with lysine (hereinafter referred to as “PASP-Lysine”). .
  • PSI Polysuccinimide
  • PASP-HDA-Lysine a polyaspartic acid derivative in which residues were simultaneously substituted with lysine and hexadecylamine.
  • PASP-Lysine and each component were introduced into the container in the composition shown in Table 1 below, dissolved at a temperature of 80 ° C., mixed for 5 minutes using a homomixer, and then continuously washed at 1,000 bar in a high pressure homogenizer. After passing through the mixture, it was cooled and defoamed to obtain a nanoemulsion.
  • Nanoemulsion was prepared in the same composition and method as Example 1 except for using PASP-HDA-Lysine instead of PASP-Lysine.
  • Particle distribution of the nanoemulsion prepared in Example 1 was measured using Photal ELS-Z and shown in FIG. 1. As a result, it was found that the diameter size of the particles was 50 to 200 nm.
  • Particles of the nanoemulsion prepared in Example 1 were taken. Since the particle size of the nanoemulsion was too fine to be measured by a general optical microscope, it was photographed using a frozen electron microscope (JEM 1010, JEOL, Japan) (FIG. 2). It can be seen from FIG. 2 that the nanoemulsion was well formed in a uniform size.
  • mice Female hairless guinea pigs (strain IAF / HA-hrBR) of about 8 weeks were used.
  • the abdominal skin of the guinea pig was excised and mounted on a Franz-type diffusion cell (Lab fine instruments, Korea).
  • 50mM phosphate buffer (pH 7.4, 0.1M Nacl) was added to the Receptor vessel (5ml) of the Franz-type diffusion cell, and then the diffusion cell was mixed and dispersed at 32 ° C. and 600 rpm.
  • the PASP-Lysine nanoemulsion 50 ⁇ l of the emulsion obtained by removing risorecithin and sucrose stearic acid ester was added to the donor container.
  • Human fibroblasts were diluted to 2.0 ⁇ 10 4 cells / ml in DMEM medium containing 0.2% FBS, 0.1% BSA. 135 ⁇ l of the cell solution was dispensed into 96 microplates, then pre-cultured in an incubator overnight, replaced with the same medium, and further incubated for 3 days by addition of PASP-lysine and PASP-HDA-lysine diluted to each concentration. After measuring the concentration of type-1 procollagen (procollagen) by ELISA method using the cell culture solution obtained after the culture is shown in Figure 3 the results.
  • type-1 procollagen procollagen
  • MMP-1 matrix metalloproteinase-1
  • PASP-Lysine and PASP-HDA-Lysine have excellent MMP-1 inhibitory effect on its own, but among these, PASP-HDA-Lysine has a higher MMP-1 inhibitory effect It was confirmed that, through this it was possible to confirm the high application potential as anti-wrinkle and anti-aging functional agonist.
  • the nanoemulsion of the present invention can be rapidly absorbed into the skin, induce collagen biosynthesis, inhibit wrinkles by inhibiting matrix metalloproteinase-1 (MMP-1), and have an excellent antiallergic effect.
  • MMP-1 matrix metalloproteinase-1

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)

Abstract

The present invention relates to a nanoemulsion comprising 1-20 parts by weight of polyaspartic acid derivative, 1-5 parts by weight of saturated lecithin, 1-10 parts by weight of dissolution aid, 0.1-5 parts by weight of rhizonlecithin, and 1-5 parts by weight of sucrose fatty acid ester, and also relates to a personal care composition containing said nanoemulsion. The personal care composition containing the nanoemulsion of the present invention can induce biosynthesis of collagen, and has very good inhibitory effects against MMP-1 (matrix metalloproteinase-1) and has anti-allergic effects.

Description

폴리아스파르트산 유도체를 함유하는 나노에멀젼 및 이를 포함하는 퍼스널 케어 조성물Nanoemulsions Containing Polyaspartic Acid Derivatives and Personal Care Compositions Comprising the Same
본 발명은 폴리아스파르트산 유도체 1 내지 20 중량부, 포화 레시친 1 내지 5 중량부, 용해 보조제 1 내지 10 중량부, 리조레시친 0.1 내지 5 중량부 및 자당 지방산 에스테르 계면활성제 1 내지 5 중량부를 포함하는 나노에멀젼, 및 이를 포함하는 퍼스널 케어 조성물에 관한 것으로 본 발명의 나노에멀젼을 포함하는 퍼스널 케어 조성물은 콜라겐 생합성을 유도할 수 있고 MMP-1(matrix metalloproteinase-1) 억제 및 항알레르기 효과가 매우 뛰어나다.The present invention relates to nanoparticles comprising 1 to 20 parts by weight of polyaspartic acid derivatives, 1 to 5 parts by weight of saturated lecithin, 1 to 10 parts by weight of dissolution aid, 0.1 to 5 parts by weight of resorcithin and 1 to 5 parts by weight of sucrose fatty acid ester surfactant. Emulsion, and a personal care composition comprising the same The personal care composition comprising the nanoemulsion of the present invention can induce collagen biosynthesis and is very excellent in inhibiting matrix metalloproteinase-1 (MMP-1) and anti-allergic effect.
바이오 산업의 발달과 함께 화장품, 식품, 의약품 분야 등에서 생체 활성을 갖는 많은 소재들이 연구되고 있으며 그에 따른 놀라운 결과가 보고되고 있다. 특히, 화장품 분야에서는 의약과 같은 효능 화장품의 개발을 위해 다양한 소재 개발 및 그에 따른 응용 연구가 진행되고 있다. 일명 기능성 및 코스메슈티컬(cosmeceutical)과 같은 용어가 생겨난 것이 그 실례라 할 수 있다. 이는 과거 분석장비나 데이터 해석, 그리고 메커니즘의 규명이라는 뒷받침이 없어 밝혀내기 어려운 복잡한 생체 물질들의 응용 한계를 현대 과학기술의 발전을 통해 그 문제점을 조금씩 해결해 나아가면서 새로운 효능 소재 개발에 전력을 기울이고 있으나, 아직까지는 미약한 발전에 불과한 실정이다. 이러한 소재들 중에서도 폴리머(polymer)라는 고분자 물질의 응용분야에서는 효능 화장품의 이슈화에도 불구하고 기능성 소재로서의 응용에 거의 기여를 못하고 있다. 현재 화장품 분야에서 응용되고 있는 폴리머는 폴리아크릴레이트류와 폴리비닐류, 다양한 분자량의 폴리에틸렌글리콜(PEG), 폴리소르베이트류, 폴리사카라이드류, 폴리실리콘류, 폴리아미노산류 및 다양한 폴리펩타이드 등이 있으나 대부분 보습 효과를 제외하고는 효능적인 면보다는 화장품 제형의 기본 틀 역할을 하는 점증제 및 사용감 개선제, 유화제 등으로 한정되어 사용되고 있을 뿐이다.With the development of the bio-industry, a lot of bio-active materials have been studied in cosmetics, food, and pharmaceutical fields, and surprising results have been reported. In particular, in the field of cosmetics, various materials have been developed for the development of efficacy cosmetics such as medicines, and applied research accordingly. An example is the creation of terms such as functionality and cosmeceutical. This is the development of new efficacious materials by gradually solving the problems through the development of modern science and technology to solve the limitation of the application of complex biological materials that are difficult to find due to the past analysis equipment, data interpretation, and mechanism identification. It is still a weak development. Among these materials, despite the issue of high-efficiency cosmetics in the field of application of polymer materials called polymers, they hardly contribute to the application as a functional material. The polymers currently applied in the cosmetic field include polyacrylates and polyvinyls, polyethylene glycol (PEG) of various molecular weights, polysorbates, polysaccharides, polysilicones, polyamino acids and various polypeptides. Except for the moisturizing effect, it is only used as a thickener, a feeling-improving agent, an emulsifier, etc., which serve as a basic framework of cosmetic formulations rather than an efficacy aspect.
따라서 본 발명은 다양한 바이오 폴리머 중 반응성과 응용성이 높고 생체 적합하며 환경 친화적 소재인 폴리아미노산계 물질을 사용하여 생리학적 효능, 특히 피부 활성을 증진시킬 수 있으면서도 고분자 물질의 경피 흡수 문제를 해결할 수 있는 방안을 제공하는 것을 그 기술적 과제로 한다.Therefore, the present invention can solve the problem of transdermal absorption of polymer materials while improving the physiological efficacy, especially skin activity, using polyamino acid-based materials which are highly reactive, applicable, biocompatible and environmentally friendly materials among various biopolymers. It is a technical task to provide a solution.
폴리아스파르트산 유도체 1 내지 20 중량부, 포화 레시친 1 내지 5 중량부, 용해 보조제 1 내지 10 중량부, 리조레시친 0.1 내지 5 중량부 및 자당 지방산 에스테르 계면활성제 1 내지 5 중량부를 포함하는 나노에멀젼.A nanoemulsion comprising 1 to 20 parts by weight of a polyaspartic acid derivative, 1 to 5 parts by weight of saturated lecithin, 1 to 10 parts by weight of dissolution aid, 0.1 to 5 parts by weight of resorcithin and 1 to 5 parts by weight of sucrose fatty acid ester surfactant.
본 발명의 나노에멀젼은 빠르게 피부에 흡수되어, 콜라겐 생합성을 유도할 수 있고 MMP-1(matrix metalloproteinase-1)을 억제하여 주름을 억제할 수 있으며, 항알레르기 효과 또한 매우 뛰어나다.The nanoemulsion of the present invention can be rapidly absorbed into the skin, induce collagen biosynthesis, inhibit wrinkles by inhibiting matrix metalloproteinase-1 (MMP-1), and have an excellent antiallergic effect.
도 1은 본 발명의 나노에멀젼의 입자 직경의 크기를 Photal ELS-Z를 사용하여 측정한 결과이다.1 is a result of measuring the size of the particle diameter of the nanoemulsion of the present invention using Photal ELS-Z.
도 2는 본 발명의 나노에멀젼을 동결 전자현미경을 사용하여 확대 촬영한 사진이다.2 is an enlarged photograph of the nanoemulsion of the present invention using a frozen electron microscope.
도 3은 콜라겐 생합성 효과를 측정하여 그 결과를 나타낸 그래프이다. (PASP: 폴리아스파르트산; PASP-Lysine: 라이신으로 치환된 폴리아스파르트산 유도체; PASP-HDA-Lysine: 라이신 및 헥사데실아민으로 치환된 폴리아스파르트산 유도체; TGF: transforming growth factor(TGF)-β)Figure 3 is a graph showing the results of measuring collagen biosynthesis effect. (PASP: polyaspartic acid; PASP-Lysine: polyaspartic acid derivative substituted with lysine; PASP-HDA-Lysine: polyaspartic acid derivative substituted with lysine and hexadecylamine; TGF: transforming growth factor (TGF) -β)
도 4는 MMP-1 억제 효과를 측정하여 그 결과를 나타낸 그래프이다. (PASP-Lysine: 라이신으로 치환된 폴리아스파르트산 유도체; PASP-HDA-Lysine: 라이신 및 헥사데실아민으로 치환된 폴리아스파르트산 유도체)4 is a graph showing the results of measuring the inhibitory effect of MMP-1. (PASP-Lysine: polyaspartic acid derivative substituted with lysine; PASP-HDA-Lysine: polyaspartic acid derivative substituted with lysine and hexadecylamine)
도 5는 항알레르기 효과를 살펴보기 위하여 비만 세포를 촬영한 현미경 사진이다.5 is a micrograph taken of mast cells to examine the anti-allergic effect.
도 6은 반응식 1 6 is Scheme 1
상기 목적을 달성하기 위하여 본 발명은 폴리아스파르트산 유도체 1 내지 20 중량부, 포화 레시친 1 내지 5 중량부, 용해 보조제 1 내지 10 중량부, 리조레시친 0.1 내지 5 중량부 및 자당 지방산 에스테르 계면활성제 1 내지 5 중량부를 포함하는 나노에멀젼을 제공한다.In order to achieve the above object, the present invention provides 1 to 20 parts by weight of a polyaspartic acid derivative, 1 to 5 parts by weight of saturated lecithin, 1 to 10 parts by weight of dissolution aid, 0.1 to 5 parts by weight of resorcinin and sucrose fatty acid ester surfactant. It provides a nanoemulsion comprising 5 parts by weight.
또한 본 발명의 상기 나노에멀젼을 포함하는 퍼스널 케어(personal care) 조성물을 제공한다.Also provided is a personal care composition comprising the nanoemulsion of the present invention.
이하에서 본 발명을 상세하게 설명한다.Hereinafter, the present invention will be described in detail.
본 발명의 일 측면에 따르면 폴리아스파르트산 유도체 1 내지 20 중량부, 포화 레시친 1 내지 5 중량부, 용해 보조제 1 내지 10 중량부, 리조레시친 0.1 내지 5 중량부 및 자당 지방산 에스테르 계면활성제 1 내지 5 중량부를 포함하는 나노에멀젼이 제공된다.According to an aspect of the present invention, 1 to 20 parts by weight of polyaspartic acid derivative, 1 to 5 parts by weight of saturated lecithin, 1 to 10 parts by weight of dissolution aid, 0.1 to 5 parts by weight of resorcinin and 1 to 5 parts by weight of sucrose fatty acid ester surfactant There is provided a nanoemulsion comprising a moiety.
아스파르트산(aspartic acid)은 동식물의 단백질을 구성하는 산성 아미노산의 하나로 사탕수수, 사탕무, 당밀 등에서 얻어지며, 면역계 및 뇌와 신경 보호, 활력/정력 증강, RNA/DNA 기능 향상, 과량의 암모니아와 혈류의 독소제거, 다른 아미노산과 생화학물질의 신진대사에 관여한다. 폴리아스파르트산(polyaspartic acid)은 생체적합성이 높고 환경친화적 소재로 의약품의 DDS(drug delievery system) 소재나 의료용 봉합사 및 인공 피부 등의 의료용 생체 재료로 사용되는 물질로 생체 내에서 가수분해되어 천천히 저분자 물질 혹은 단량체로 분해되어 세포나 장기에 의한 신진대사를 통해 흡수됨으로써 상처 치유 및 손상된 조직의 복원 등에 영향을 미치는 것으로 보고되어 있다.Aspartic acid is an acidic amino acid that forms the protein of plants and animals. It is obtained from sugarcane, sugar beet, and molasses. It protects the immune system and brain and nerves, enhances vitality and energy, improves RNA / DNA function, and excessive ammonia and blood flow. Toxins are involved in the metabolism of other amino acids and biochemicals. Polyaspartic acid is a biocompatible and environmentally friendly material that is used as a material for medical drugs such as drug delievery system (DDS) of medicines, medical sutures, artificial skin, etc. Or it is broken down into monomers and absorbed through metabolism by cells or organs, which has been reported to affect wound healing and restoration of damaged tissues.
본 발명에서 폴리아스파르트산 유도체는 L-아스파르트산을 이용하여 산촉매 하에서 축중합을 통해 폴리숙신이미드(polysuccinimide; PSI)를 합성하고 이를 가수분해 및 산성화시켜 폴리아스파르트산을 제조한 다음 이를 라이신, 또는 라이신과 알킬아민을 동시에 결합시켜 폴리아스파르트산의 반복된 카르복실산기와 라이신의 아민기, 또는 라이신과 알킬아민의 각각의 아민기와의 펩타이드 결합 반응을 통하여 폴리아스파르트산의 하나 이상의 잔기를 치환함으로써 제조될 수 있다.In the present invention, the polyaspartic acid derivative is synthesized polysuccinimide (PSI) by condensation polymerization under an acid catalyst using L-aspartic acid, and hydrolyzed and acidified to prepare polyaspartic acid followed by lysine, or By combining lysine and alkylamine simultaneously to replace one or more residues of polyaspartic acid through a peptide bond reaction of the repeated carboxylic acid group of polyaspartic acid with the amine group of lysine or the respective amine group of lysine and alkylamine Can be.
본 발명에 따른 일 구체예에서 폴리아스파르트산 유도체는 다음의 도 6(반응식 1)에 따라 폴리아스파르트산의 하나 이상의 잔기에 라이신, 또는 라이신과 알킬아민을 동시에 결합시켜 제조된다.In one embodiment according to the present invention, the polyaspartic acid derivative is prepared by simultaneously combining lysine, or lysine and alkylamine, to one or more residues of polyaspartic acid according to the following FIG. 6 (Scheme 1).
반응식 1을 도 6을 대체한다. Scheme 1 replaces FIG. 6.
상기 반응식 1(도 6)에서 R은 -OH 또는 C10-20 알킬아민이고, 예컨대 n은 20 내지 1,000, m은 20 내지 1,500이다.In Scheme 1 (FIG. 6), R is —OH or C 10-20 alkylamine, such as n is from 20 to 1,000 and m is from 20 to 1500.
본 발명에서 C10-20 알킬아민은 예를 들면, 데실아민(decylamine), 도데실아민(dodecylamine), 펜타데실아민(pentadecylamine), 헥사데실아민(hexadecylamine), 헵타데실아민(heptadecylamine), 옥타데실아민(octadecylamine) 등의 알킬아민류가 사용될 수 있으나 이에 제한되는 것은 아니다.In the present invention, C 10-20 alkylamine is, for example, decylamine, dodecylamine, dodecylamine, pentadecylamine, hexadecylamine, heptadecylamine, heptadecylamine, octadecyl, octadecyl Alkylamines such as amines (octadecylamine) may be used, but are not limited thereto.
라이신은 아미노산 중의 하나로 곡물을 위주로 한 동양인에게 특히 부족하기 쉬울 뿐만 아니라, 인체의 성장기에 보다 많이 필요로 되는 필수 아미노산으로 보고되어 있는데, 성장 인자(growth factor)에 관여하는 것으로 알려져 있으나, 체내에서 합성되지 않으며 다양한 아미노산과 혼합 형태로 사용되기에 그 기능에 대해 많이 알려져 있지 않고, 거의 모든 단백질 구조에 포함되어 있으며, 특히 히스톤, 알부민, 근육 단백질 등에 많다. Lysine, one of the amino acids, is not only easily lacked by Asians, especially grains, but is also reported to be an essential amino acid that is needed more in the growth phase of the human body, but is known to be involved in growth factors. It is not known much about its function because it is used in combination with various amino acids, it is included in almost all protein structures, especially histones, albumin, muscle protein and the like.
본 발명에서는 폴리아스팔틱산 유도체가 바람직하게는 분자량이 5,000 내지 200,000 정도의 고분자라는 점에서 경피 흡수라는 문제 해결과 피부 활성의 극대화를 위해 나노에멀젼 기술을 도입함으로써 이를 해결하였다. In the present invention, the polyasphatic acid derivative is preferably a polymer having a molecular weight of about 5,000 to 200,000, thereby solving the problem of transdermal absorption and introducing nanoemulsion technology for maximizing skin activity.
본 발명에서 나노에멀젼은 폴리아스파르트산 유도체 1 내지 20 중량부, 포화 레시친 1 내지 5 중량부, 용해 보조제 1 내지 10 중량부, 리조레시친 0.1 내지 5 중량부 및 자당 지방산 에스테르 계면활성제 1 내지 5 중량부를 잔량의 물, 예를 들면 55 내지 95.9 중량부의 물에 투입한 다음 혼합하여 제조할 수 있다.In the present invention, the nanoemulsion is 1 to 20 parts by weight of polyaspartic acid derivative, 1 to 5 parts by weight of saturated lecithin, 1 to 10 parts by weight of dissolution aid, 0.1 to 5 parts by weight of resorcinin and 1 to 5 parts by weight of sucrose fatty acid ester surfactant. It can be prepared by adding a residual amount of water, for example, 55 to 95.9 parts by weight of water and then mixing.
본 발명의 나노에멀젼은 포화 레시친을 1 내지 5 중량부, 바람직하게는 1.2 내지 4 중량부, 더 바람직하게는 1.5 내지 3 중량부 포함한다. 본 발명에서 포화 레시친은 나노에멀젼의 막을 형성하는데 레시친은 동물 조직 내에 존재하는 물질로 피부와의 친화도가 우수하다. 본 발명에서 레시친은 다양한 포스포리피드의 혼합물을 지칭하고, 포스포리피드의 조성은 그 기원(origin)에 따라 다양할 수 있다. 포화 레시친은 레시친을 수소화(hydrogenation)시켜 지방산의 탄화수소 사슬 중의 이중결합을 모두 단일결합으로 바꿔서 제조할 수 있고, 포화 레시친은 그 색상이 백색으로 우수하기에 특히 화장품의 적용에 바람직하게 사용될 수 있다. 본 발명에서 포화 레시친이 1 중량부 미만으로 포함되면 나노에멀젼의 형성에 문제가 있을 수 있고 5 중량부를 초과하여 포함되면 막 성분의 과다로 인하여 에멀젼 내에 포접되는 성분의 양이 작아짐에 따라 본 발명의 나노에멀젼의 효과가 불충분해진다는 문제가 있을 수 있다.The nanoemulsion of the present invention contains 1 to 5 parts by weight, preferably 1.2 to 4 parts by weight, more preferably 1.5 to 3 parts by weight of saturated lecithin. In the present invention, saturated lecithin forms a membrane of nanoemulsion, and lecithin is a substance present in animal tissue and has excellent affinity with skin. In the present invention, lecithin refers to a mixture of various phospholipids, and the composition of phospholipids may vary depending on their origin. Saturated lecithin can be prepared by hydrogenating lecithin to convert all double bonds in the hydrocarbon chain of fatty acids into single bonds. Saturated lecithin is excellent in its white color and can be particularly preferably used in cosmetic applications. If less than 1 part by weight of saturated lecithin is included in the present invention, there may be a problem in the formation of the nanoemulsion, and if it is included in excess of 5 parts by weight, the amount of components contained in the emulsion may be reduced due to the excessive amount of membrane components. There may be a problem that the effect of the nanoemulsion becomes insufficient.
본 발명의 나노에멀젼은 용해 보조제를 1 내지 10 중량부, 바람직하게는 2 내지 8 중량부 포함한다. 본 발명에서 용해 보조제는 폴리아스파르트산 유도체의 용해를 돕는 역할을 하고, 바람직하게는 에탄올이다. 본 발명에서 용해 보조제가 1 중량부 미만으로 포함되면 폴리아스파르트산 유도체의 용해를 돕는 효과가 미약해질 수 있고, 10 중량부를 초과하여 포함되면 유화 안정성이 저하될 수 있다.The nanoemulsion of the present invention contains 1 to 10 parts by weight, preferably 2 to 8 parts by weight of the dissolution aid. The dissolution aid in the present invention serves to help dissolution of the polyaspartic acid derivative, preferably ethanol. In the present invention, when the dissolution aid is included in less than 1 part by weight, the effect of assisting the dissolution of the polyaspartic acid derivative may be weakened, and when included in excess of 10 parts by weight, the emulsion stability may be lowered.
본 발명의 나노에멀젼은 리조레시친(lysolecithin)을 0.1 내지 5 중량부, 바람직하게는 0.5 내지 4 중량부 포함한다. 본 발명에서 리조레시친은 포화 레시친과 더불어 나노에멀젼의 계면막을 더욱 튼튼하게 만들어준다. 본 발명에서 리조레시친이 0.1 중량부 미만으로 포함되면 나노에멀젼의 형성시 리조레시친에 의한 효과가 미약해질 수 있고 5 중량부를 초과하여 포함되면 나노에멀젼이 불안정해 질 수 있다.The nanoemulsion of the present invention contains 0.1 to 5 parts by weight, preferably 0.5 to 4 parts by weight of lysolecithin. Resorcinin in the present invention, together with saturated lecithin, makes the interfacial film of the nanoemulsion more robust. In the present invention, when the resorcithin is included in less than 0.1 part by weight, the effect of the resorcithin may be weakened when the nanoemulsion is formed, and when included in excess of 5 parts by weight, the nanoemulsion may become unstable.
본 발명의 나노에멀젼은 자당 지방산 에스테르 계면활성제를 1 내지 5 중량부, 바람직하게는 2 내지 4 중량부 포함한다. 본 발명에서 자당 지방산 에스테르 계면활성제는 나노에멀젼의 막을 형성한다. 본 발명에서 자당 지방산 에스테르 계면활성제는, 예를 들면 자당 스테아린산 에스테르, 자당 팔미틴산 에스테르, 자당 미리스틴산 에스테르, 자당 올레인산 에스테르 및 자당 라우린산 에스테르가 사용될 수 있으나 이에 제한되는 것은 아니다. 본 발명에서 자당 지방산 에스테르 계면활성제가 1 중량부 미만으로 포함되면 나노에멀젼의 형성에 문제가 있을 수 있고 5 중량부를 초과하여 포함되면 막 성분의 과다로 인하여 에멀젼 내에 포접되는 성분의 양이 작아짐에 따라 본 발명의 나노에멀젼의 효과가 불충분해진다는 문제가 있을 수 있다.The nanoemulsion of the present invention contains 1 to 5 parts by weight, preferably 2 to 4 parts by weight of a sucrose fatty acid ester surfactant. Sucrose fatty acid ester surfactants in the present invention form a film of nanoemulsion. Sucrose fatty acid ester surfactant in the present invention, for example, sucrose stearic acid ester, sucrose palmitate ester, sucrose myristic acid ester, sucrose oleic acid ester and sucrose lauric acid ester may be used, but is not limited thereto. If the sucrose fatty acid ester surfactant is included in less than 1 part by weight in the present invention may be a problem in the formation of the nanoemulsion and if it is included in excess of 5 parts by weight as the amount of components contained in the emulsion due to the excess of the membrane component is reduced There may be a problem that the effect of the nanoemulsion of the present invention becomes insufficient.
본 발명에서 나노에멀젼의 제조는 당 분야에 공지된 다양한 방법에 의하여 이루어질 수 있고 이에 따른 특별한 제한은 없다. 본 발명에서 나노에멀젼은 그 입자 직경의 크기가 바람직하게는 약 50 내지 200㎚이다. 나노에멀젼의 입자 직경의 크기가 약 50 내지 200㎚이면 피부로의 침투가 용이해질 수 있다.Preparation of the nanoemulsion in the present invention can be made by a variety of methods known in the art and there is no particular limitation thereto. In the present invention, the nanoemulsion has a particle diameter of preferably about 50 to 200 nm. When the particle diameter of the nanoemulsion is about 50 to 200 nm, penetration into the skin may be facilitated.
본 발명의 다른 측면에 따르면 본 발명의 나노에멀젼을 포함하는 퍼스널 케어(personal care) 조성물이 제공된다.According to another aspect of the invention there is provided a personal care composition comprising the nanoemulsion of the invention.
본 발명에서 퍼스널 케어 조성물은 스킨 케어 조성물, 바디 케어 조성물, 헤어 케어 조성물 등을 의미하고, 그 구체적인 예로는 바디 로션, 샴푸, 린스, 크림, 로션, 에센스, 스킨 등이 있으나 이에 제한되는 것은 아니다.In the present invention, the personal care composition means a skin care composition, a body care composition, a hair care composition, and the like, and specific examples thereof include, but are not limited to, body lotion, shampoo, rinse, cream, lotion, essence, skin, and the like.
본 발명의 퍼스널 케어 조성물은 본 발명에 따른 나노에멀젼을 바람직하게는 1 내지 10 중량%, 더 바람직하게는 2 내지 8 중량% 포함한다. 본 발명에서 퍼스널 케어 조성물이 나노에멀젼을 1 중량% 미만으로 포함하면 나노에멀젼이 제공하는 효과가 미비해질 수 있고, 10 중량%를 초과하여 포함하더라도 나노에멀젼이 제공하는 효과가 그 첨가되는 것에 비례하여 증가하는 것을 더 이상 기대하기 어려워 경제상 바람직하지 않다.The personal care composition of the present invention preferably comprises 1 to 10% by weight, more preferably 2 to 8% by weight of the nanoemulsion according to the invention. In the present invention, when the personal care composition contains less than 1% by weight of the nanoemulsion, the effect provided by the nanoemulsion may be insignificant, and even if it contains more than 10% by weight, the effect provided by the nanoemulsion is in proportion to the addition thereof. It is hard to expect any more growth and is not economically desirable.
이하에서 본 발명을 실시예에 의하여 구체적으로 설명한다. 다만 실시예는 본 발명의 이해를 돕기 위하여 예시하는 것일 뿐 이에 의하여 본 발명의 범위가 제한되는 것은 아니다.Hereinafter, the present invention will be described in detail by way of examples. However, the embodiments are only illustrated to help the understanding of the present invention, and the scope of the present invention is not limited thereto.
제조예 1: PASP-Lysine의 제조Preparation Example 1 Preparation of PASP-Lysine
L-아스파르트산을 인산을 촉매로 하여 180℃에서 감압하에 폴리숙신이미드(polysuccinimide, PSI)를 합성하였다. 합성된 PSI를 0.1N NaOH를 이용하여 가수분해한 후 0.1N HCl로 산성화(acidify)하여 폴리(아스파르트산)(PASP)을 제조한 다음, N,N′-디사이클로헥실 카르보디이미드(N,N′-dicyclohexyl carbodiimide, DCC)를 커플링제로 이용하여 DMF 용매하에서 L-라이신과 60℃에서 24시간 동안 반응하여 잔기가 라이신으로 치환된 폴리아스파르트산 유도체(이하에서 “PASP-Lysine”)을 얻었다.Polysuccinimide (PSI) was synthesized using L-aspartic acid as a catalyst under phosphoric acid at 180 ° C. The synthesized PSI was hydrolyzed with 0.1N NaOH and acidified with 0.1N HCl to prepare poly (aspartic acid) (PASP), followed by N, N′-dicyclohexyl carbodiimide (N, N'-dicyclohexyl carbodiimide (DCC) was used as a coupling agent to react with L-lysine for 24 hours at 60 ° C. in a DMF solvent to obtain a polyaspartic acid derivative having a residue substituted with lysine (hereinafter referred to as “PASP-Lysine”). .
제조예 2: PASP-HDA-Lysine의 제조Preparation Example 2 Preparation of PASP-HDA-Lysine
L-아스파르트산을 인산을 촉매로 하여 180℃에서 감압하에 폴리숙신이미드(polysuccinimide, PSI)를 합성하였다. DMF 용매하에서 합성된 PSI와 헥사데실아민을 80℃에서 24시간 반응하여 PSI와 헥사데실아민이 결합된 PSI-HDA를 얻었다. 이렇게 얻어진 PSI-HDA를 제조예 1에서와 같이 0.1N NaOH를 이용하여 잔존하는 PSI 반복단위를 가수분해한 후 0.1N HCl로 산성화하여 폴리(아스파르트산)-헥사데실아민(PASP-HDA)을 합성하였다. 여기에 제조예 1과 동일한 방법으로 PASP 반복단위와 L-라이신을 결합하여 잔기가 라이신 및 헥사데실아민으로 동시에 치환된 폴리아스파르트산 유도체(이하에서 “PASP-HDA-Lysine”)를 얻었다.Polysuccinimide (PSI) was synthesized using L-aspartic acid as a catalyst under phosphoric acid at 180 ° C. PSI synthesized in DMF solvent and hexadecylamine were reacted at 80 ° C. for 24 hours to obtain PSI-HDA in which PSI and hexadecylamine were combined. The PSI-HDA thus obtained was hydrolyzed with 0.1 N NaOH using 0.1 N NaOH, and then acidified with 0.1 N HCl to synthesize poly (aspartic acid) -hexadecylamine (PASP-HDA). It was. In the same manner as in Preparation Example 1, a PASP repeating unit and L-lysine were combined to obtain a polyaspartic acid derivative (hereinafter, “PASP-HDA-Lysine”) in which residues were simultaneously substituted with lysine and hexadecylamine.
실시예 1: PASP-Lysine 나노에멀젼의 제조Example 1 Preparation of PASP-Lysine Nanoemulsion
PASP-Lysine 및 각 성분을 다음의 표 1의 조성으로 용기에 도입하여 80℃의 온도에서 용해시키고 나서, 호모 믹서를 이용하여 5분 동안 혼합한 다음 고압 균질화기(microfluidizer)에서 1,000 bar로 연속 3회 통과시킨 후 냉각, 탈포시켜 나노에멀젼을 얻었다.PASP-Lysine and each component were introduced into the container in the composition shown in Table 1 below, dissolved at a temperature of 80 ° C., mixed for 5 minutes using a homomixer, and then continuously washed at 1,000 bar in a high pressure homogenizer. After passing through the mixture, it was cooled and defoamed to obtain a nanoemulsion.
표 1
성분 함량(중량%)
포화 레시친에탄올PASP-Lysine리조레시친자당 스테아린산 에스테르정제수 2.56123274.5
합계 100
Table 1
ingredient Content (% by weight)
Saturated lecithin ethanol PASP-Lysine resort lecithin sugar stearic acid ester 2.56123274.5
Sum 100
실시예 2: PASP-HDA-Lysine 나노에멀젼의 제조Example 2: Preparation of PASP-HDA-Lysine Nanoemulsion
PASP-Lysine 대신 PASP-HDA-Lysine을 사용한 것을 제외하고는 실시예 1과 동일한 조성 및 방법으로 나노에멀젼을 제조하였다.Nanoemulsion was prepared in the same composition and method as Example 1 except for using PASP-HDA-Lysine instead of PASP-Lysine.
실시예 3: 바디 로션의 제조Example 3: Preparation of Body Lotion
다음의 표 2의 조성으로 나노에멀젼을 이용하여 바디 로션을 제조하였다.To prepare a body lotion using a nanoemulsion in the composition of Table 2.
표 2
성분 함량(중량%)
A 폴리글리세리-3 메틸 글루코스 디스테아레이트디카프릴릭 카보네이트카프릭/카프릴릭 트리글리세라이드해바라기 오일올리브 오일 33255
B 글리세린정제수 869
C 나노에멀젼 5
합계 100
TABLE 2
ingredient Content (% by weight)
A Polyglycerol-3 Methyl Glucose Distearate Dicaprylic Carbonate Capric / Caprylic Triglyceride Sunflower Oil Olive Oil 33255
B Glycerin Purified Water 869
C Nano Emulsion 5
Sum 100
실시예 4: 샴푸의 제조Example 4: Preparation of Shampoo
다음의 표 3의 조성으로 나노에멀젼을 이용하여 샴푸를 제조하였다.Shampoo was prepared using the nanoemulsion in the composition of Table 3 below.
표 3
성분 함량(중량%)
소듐 라우릴 에테르 설페이트 (SLES)코코지방산 디에톨아미드코코아미드프로필 베타인프로필렌 글리콜폴리아크릴아마이드NaClEDTA나노에멀젼정제수 402330.410.1545.5
합계 100
TABLE 3
ingredient Content (% by weight)
Sodium lauryl ether sulfate (SLES) coco fatty acid dietholamide cocoamide propyl betaine propylene glycol polyacrylamide NaClEDTA nanoemulsion 402330.410.1545.5
Sum 100
실시예 5: 린스의 제조Example 5: Preparation of Rinse
다음의 표 4의 조성으로 나노에멀젼을 이용하여 린스를 제조하였다.To prepare a rinse using a nanoemulsion in the composition of Table 4.
표 4
성분 함량(중량%)
세테아릴알코올스테아릴알코올세탄올폴리아크릴아마이드EDTAPEG-800수용성 실리콘디스테아릴-디메틸 암모늄 클로라이드세틸-트리메틸-암모늄 클로라이드나노에멀젼정제수 0.50.510.20.051122586.75
합계 100
Table 4
ingredient Content (% by weight)
Cetearyl Alcohol Stearyl Alcohol Cetanol Polyacrylamide EDTAPEG-800 Water Soluble Silicone Distearyl-Dimethyl Ammonium ChlorideCetyl-trimethyl-ammonium Chloride Nanoemulsion 0.50.510.20.051122586.75
Sum 100
실시예 6: 크림의 제조Example 6: Preparation of Cream
다음의 표 5의 조성으로 나노에멀젼을 이용하여 크림을 제조하였다.To prepare a cream using a nanoemulsion in the composition of Table 5.
표 5
성분 함량(중량%)
솔비탄 스테아레이트/수크로스코코에이트세테아릴알코올마카다미아넛 오일올리브 오일실리콘 오일글리세린카보폴나노에멀젼정제수 41.563180.36571.14
합계 100
Table 5
ingredient Content (% by weight)
Sorbitan stearate / sucrose cocoate cetearyl alcohol macadamia nut oil olive oil silicone oil glycerin carbopolano emulsion 41.563180.36571.14
Sum 100
실시예 7: 로션의 제조Example 7: Preparation of Lotion
다음의 표 6의 조성으로 나노에멀젼을 이용하여 로션을 제조하였다.To prepare a lotion using a nanoemulsion in the composition of Table 6.
표 6
성분 함량(중량%)
폴리글리세릴-3-메틸글루코스 디스테아레이트세테아릴알코올올리브 오일카프릭/카프릴릭 트리글리세라이드실리콘 오일글리세린카보폴나노에멀젼정제수 20.554450.2574.3
합계 100
Table 6
ingredient Content (% by weight)
Polyglyceryl-3-methylglucose distearate cetearyl alcohol olive oil capric / caprylic triglyceride silicone oil glycerin carbopolnano emulsion 20.554450.2574.3
Sum 100
실시예 8: 에센스의 제조Example 8 Preparation of Essence
다음의 표 7의 조성으로 나노에멀젼을 이용하여 에센스를 제조하였다.Essence was prepared using a nanoemulsion in the composition of Table 7 below.
표 7
성분 함량(중량%)
루브라젤카보폴PEG-1500글리세린나노에멀젼정제수 150.437569.6
합계 100
TABLE 7
ingredient Content (% by weight)
Lubra gel carbopol PEG-1500 glycerin nano emulsion 150.437569.6
Sum 100
실시예 9: 스킨의 제조Example 9: Preparation of Skin
다음의 표 8의 조성으로 나노에멀젼을 이용하여 스킨을 제조하였다.To prepare a skin using a nanoemulsion in the composition of Table 8.
표 8
성분 함량(중량%)
글리세린PEG-1500글루탐산나노에멀젼정제수 731584
합계 100
Table 8
ingredient Content (% by weight)
Glycerin PEG-1500 Glutamic Acid Nanoemulsion 731584
Sum 100
실험예 1: 나노에멀젼의 입자 분포 측정Experimental Example 1 Measurement of Particle Distribution of Nanoemulsion
실시예 1에서 제조된 나노에멀젼의 입자 분포를 Photal ELS-Z를 이용하여 측정하여 도 1에 나타내었다. 측정 결과 입자의 직경 크기가 50 내지 200㎚임을 알 수 있었다.Particle distribution of the nanoemulsion prepared in Example 1 was measured using Photal ELS-Z and shown in FIG. 1. As a result, it was found that the diameter size of the particles was 50 to 200 nm.
실험예 2: 나노에멀젼 입자 촬영Experimental Example 2: Nanoemulsion Particles
실시예 1에서 제조된 나노에멀젼의 입자를 촬영하였다. 나노에멀젼의 입자 크기가 너무 미세하여 일반적인 광학 현미경으로는 측정이 불가능하기에 동결 전자현미경(JEM 1010, JEOL사, 일본)을 이용하여 촬영하였다(도 2). 도 2로부터 나노에멀젼이 균일한 크기로 잘 형성되었음을 알 수 있었다.Particles of the nanoemulsion prepared in Example 1 were taken. Since the particle size of the nanoemulsion was too fine to be measured by a general optical microscope, it was photographed using a frozen electron microscope (JEM 1010, JEOL, Japan) (FIG. 2). It can be seen from FIG. 2 that the nanoemulsion was well formed in a uniform size.
실험예 3: PASP-Lysine의 경피 흡수촉진 효과 실험Experimental Example 3: Percutaneous absorption promoting effect experiment of PASP-Lysine
8주 정도의 암컷 무모 기니아피그(strain IAF/HA-hrBR)를 이용하였다. 기니아피그의 복부 피부를 절취한후 Franz-type diffusion cell(Lab fine instruments, korea)에 장착하여 실험하였다. Franz-type diffusion cell의 Receptor용기(5㎖)에 50mM 인산염 완충액(pH 7.4, 0.1M Nacl)을 넣어준 후, diffusion cell을 32℃, 600 rpm으로 혼합, 분산시켜 주었으며, 상기 PASP-Lysine 나노에멀젼, 및 성분에서 리조레시친과 자당 스테아린산 에스테르를 뺀 에멀젼 50㎕를 donor용기에 넣어 주었다. 예정한 시간에 따라 흡수 확산시켜 주었으며, 흡수 확산이 일어나는 피부는 0.64 cm2가 되게 하였다. 유효성분의 흡수확산이 끝난 후에는 건조된 kimwipes 또는 10㎖의 에탄올로 흡수되지 못하고 피부에 남아 있는 유화물을 씻어주고, 팁-타입 균질기(homogenizer)를 사용하여 유효성분이 흡수 확산되어 있는 피부를 갈아준 후, 피부 내부로 흡수된 PASP-Lysine을 4㎖의 디클로로메탄을 사용하여 추출하였다. 이후 추출액을 0.45㎛ 나일론 멤브레인(nylon membrane) 여과막으로 여과하고, 다음 조건으로 HPLC법으로 함량을 측정한 후에 그 결과를 표 9에 나타내었다.Female hairless guinea pigs (strain IAF / HA-hrBR) of about 8 weeks were used. The abdominal skin of the guinea pig was excised and mounted on a Franz-type diffusion cell (Lab fine instruments, Korea). 50mM phosphate buffer (pH 7.4, 0.1M Nacl) was added to the Receptor vessel (5ml) of the Franz-type diffusion cell, and then the diffusion cell was mixed and dispersed at 32 ° C. and 600 rpm. The PASP-Lysine nanoemulsion 50 μl of the emulsion obtained by removing risorecithin and sucrose stearic acid ester was added to the donor container. Absorption and diffusion were carried out according to the scheduled time, and the skin where absorption and diffusion occurred was 0.64 cm 2 . After the diffusion of the active ingredient is finished, wash the emulsion remaining on the skin that is not absorbed by dried kimwipes or 10ml of ethanol, and grind the skin where the active ingredient is absorbed and diffused using a tip-type homogenizer. After absorption, PASP-Lysine absorbed into the skin was extracted using 4 ml of dichloromethane. Thereafter, the extract was filtered with a 0.45 μm nylon membrane filtration membrane, and the content was measured by HPLC under the following conditions.
- 컬럼: C18(4.6 × 200mm, 5㎛)Column: C18 (4.6 × 200 mm, 5 μm)
- 이동상: 메탄올Mobile phase: methanol
- 유속: 0.8㎖/minFlow rate: 0.8 ml / min
- 검출기: UV 275nmDetector: UV 275 nm
표 9
경피 흡수량 (㎍) 경피 흡수 증가율
리조레시친과 자당지방에스테르를 뺀 나노에멀젼 0.3 -
리조레시친과 자당지방에스테르를 함유하는 나노에멀젼 2.0 6.7배
Table 9
Percutaneous absorption (㎍) Percutaneous Absorption Increase
Nanoemulsion without risorecithin and sucrose fat ester 0.3 -
Nanoemulsion Containing Risorcithin and Sucrose Fatty Ester 2.0 6.7 times
실험예 4: 콜라겐 생합성 효과Experimental Example 4: Collagen Biosynthesis Effect
인간 섬유아세포(HDFN)를 0.2% FBS, 0.1% BSA를 함유한 DMEM 배지에 2.0 × 104 cells/㎖가 되도록 희석하였다. 이 세포액 135㎕를 96 microplate에 분주한 다음 배양기에서 밤새 pre-culture하고, 동일한 배지로 교체한 후, 각 농도로 희석된 PASP-lysine 및 PASP-HDA-lysine을 첨가하여 3일간 추가 배양하였다. 배양 후 얻은 세포배양액을 이용하여 ELISA법으로 type-1 프로콜라겐(procollagen)의 농도를 측정한 다음 그 결과를 도 3에 나타내었다.Human fibroblasts (HDFN) were diluted to 2.0 × 10 4 cells / ml in DMEM medium containing 0.2% FBS, 0.1% BSA. 135 μl of the cell solution was dispensed into 96 microplates, then pre-cultured in an incubator overnight, replaced with the same medium, and further incubated for 3 days by addition of PASP-lysine and PASP-HDA-lysine diluted to each concentration. After measuring the concentration of type-1 procollagen (procollagen) by ELISA method using the cell culture solution obtained after the culture is shown in Figure 3 the results.
도 3에서 볼 수 있듯이, PASP-lysine 및 PASP-HDA-lysine을 첨가한 세포에서의 콜라겐 생성이 그 농도에 비례하여 증가되는 것을 확인할 수 있었다. 이 증가율은 양성 대조군(positive control)으로 이용한 TGF-β1의 효과보다도 높은 것으로 매우 의미 있는 수준이라고 판단되었다.As can be seen in Figure 3, it was confirmed that collagen production in the cells added with PASP-lysine and PASP-HDA-lysine increased in proportion to the concentration. This increase rate was higher than the effect of TGF-β1 used as a positive control, it was judged to be a very significant level.
실험예 5: PASP-Lysine 및 PASP-HDA-Lysine의 MMP-1 억제 효과Experimental Example 5: MMP-1 Inhibitory Effect of PASP-Lysine and PASP-HDA-Lysine
PASP-Lysine 및 PASP-HDA-Lysine의 MMP-1(matrix metalloproteinase-1) 억제 효과를 측정한 다음 그 결과를 도 4에 나타내었다. 도 4로부터 알 수 있듯이, 폴리아스파르트산 유도체인 PASP-Lysine 및 PASP-HDA-Lysine 모두 자체적으로 우수한 MMP-1억제 효과가 있으나, 이 중 PASP-HDA-Lysine이 더 높은 MMP-1억제 효과가 나타남을 확인할 수 있었고, 이를 통해 항주름 및 항노화 기능성 효능 물질로의 높은 응용 가능성을 확인할 수 있었다. The results of measuring the inhibition of matrix metalloproteinase-1 (MMP-1) of PASP-Lysine and PASP-HDA-Lysine are shown in FIG. 4. As can be seen from Figure 4, both the polyaspartic acid derivatives PASP-Lysine and PASP-HDA-Lysine has excellent MMP-1 inhibitory effect on its own, but among these, PASP-HDA-Lysine has a higher MMP-1 inhibitory effect It was confirmed that, through this it was possible to confirm the high application potential as anti-wrinkle and anti-aging functional agonist.
실험예 6: 비만세포를 이용한 PASP-Lysine 나노에멀젼의 항알레르기 효과Experimental Example 6: Anti-allergic effect of PASP-Lysine nanoemulsion using mast cells
비만세포(mast cell)에 자극제인 C48/80을 처리하였을 경우 세포벽이 허물어져 탈과립되는 현상, 즉 세포벽이 터져 사멸되는 현상을 나타내고 이에 따라 세포 내에 존재하는 히스타민이 배출되어 피부에 가려움과 알레르기를 일으키게 되는 것을 이용하여 PASP-Lysine 나노에멀젼의 항알레르기 효과를 확인하였다.Treatment of mast cells with C48 / 80, a stimulant, causes cell walls to collapse and degranulate, ie cell walls burst and die, resulting in the release of histamine present in the cells, causing itching and allergies to the skin. It was confirmed that the anti-allergic effect of PASP-Lysine nanoemulsion using.
비만세포를 자극제인 C48/80과 함께 물 또는 PASP-Lysine 나노에멀젼을 처리한 다음 현미경으로 촬영하여 비교하였다(도 5). 도 5로부터 볼 수 있듯이 PASP-Lysine 나노에멀젼을 처리한 비만세포(mast cell)에서는 자극제에 처리한 경우에도 세포가 원형 그대로 유지됨을 확인할 수 있었다. 세포 내에 존재하는 히스타민이 자극제(원)의 영향에도 불구하고 세포가 외부 스트레스로부터 탈과립 현상이 나타나지 않아 알레르기를 유발하는 히스타민이 유출이 되지 않았다는 사실로부터 본원 발명의 PASP-Lysine 나노에멀젼의 항알레르기 효과를 확인할 수 있었다.Mast cells were treated with water or PASP-Lysine nanoemulsion with C48 / 80 as a stimulant and then photographed under a microscope (FIG. 5). As can be seen from Figure 5 in the mast cells treated with PASP-Lysine nanoemulsion (mast cell) was confirmed that the cells remain intact even when treated with a stimulant. The antiallergic effect of the PASP-Lysine nanoemulsion of the present invention was prevented from the fact that the histamine present in the cell did not show degranulation from external stress despite the influence of the stimulant (source). I could confirm it.
본 발명의 나노에멀젼은 빠르게 피부에 흡수되어, 콜라겐 생합성을 유도할 수 있고 MMP-1(matrix metalloproteinase-1)을 억제하여 주름을 억제할 수 있으며, 항알레르기 효과 또한 매우 뛰어나다.The nanoemulsion of the present invention can be rapidly absorbed into the skin, induce collagen biosynthesis, inhibit wrinkles by inhibiting matrix metalloproteinase-1 (MMP-1), and have an excellent antiallergic effect.

Claims (7)

  1. 폴리아스파르트산 유도체 1 내지 20 중량부, 포화 레시친 1 내지 5 중량부, 용해 보조제 1 내지 10 중량부, 리조레시친 0.1 내지 5 중량부 및 자당 지방산 에스테르 계면활성제 1 내지 5 중량부를 포함하는 나노에멀젼.A nanoemulsion comprising 1 to 20 parts by weight of a polyaspartic acid derivative, 1 to 5 parts by weight of saturated lecithin, 1 to 10 parts by weight of dissolution aid, 0.1 to 5 parts by weight of resorcithin and 1 to 5 parts by weight of sucrose fatty acid ester surfactant.
  2. 제1항에 있어서, 상기 폴리아스파르트산 유도체가 폴리아스파르트산의 하나 이상의 잔기가 라이신, 또는 라이신 및 C10-20 알킬아민으로 동시에 치환된 것임을 특징으로 나노에멀젼.The nanoemulsion of claim 1, wherein the polyaspartic acid derivative is one or more residues of polyaspartic acid substituted simultaneously with lysine, or lysine and C 10-20 alkylamine.
  3. 제2항에 있어서, C10-20 알킬아민이 데실아민, 이루도데실아민, 펜타데실아민, 헥사데실아민, 헵타데실아민 및 옥타데실아민으로 이루어지는 그룹으로부터 선택되는 적어도 하나인 것을 특징으로 하는 나노에멀젼.3. The nanoparticle of claim 2 wherein the C 10-20 alkylamine is at least one selected from the group consisting of decylamine, irdodecylamine, pentadecylamine, hexadecylamine, heptadecylamine and octadecylamine. emulsion.
  4. 제1항에 있어서, 상기 용해 보조제가 에탄올인 것을 특징으로 하는 나노에멀젼.The nanoemulsion of claim 1 wherein said dissolution aid is ethanol.
  5. 제1항에 있어서, 상기 자당 지방산 에스테르 계면활성제가 자당 스테아린산 에스테르, 자당 팔미틴산 에스테르, 자당 미리스틴산 에스테르, 자당 올레인산 에스테르 및 자당 라우린산 에스테르로 이루어지는 그룹으로부터 선택되는 적어도 하나인 것을 특징으로 하는 나노에멀젼.According to claim 1, wherein the sucrose fatty acid ester surfactant is at least one selected from the group consisting of sucrose stearic acid ester, sucrose palmitate ester, sucrose myristic acid ester, sucrose oleic acid ester and sucrose lauric acid ester emulsion.
  6. 제1항 내지 제5항 중 어느 한 항의 나노에멀젼을 포함하는 퍼스널 케어(personal care) 조성물.A personal care composition comprising the nanoemulsion of claim 1.
  7. 제6항에 있어서, 나노에멀젼을 1 내지 10 중량%로 포함하는 것을 특징으로 하는 퍼스널 케어 조성물.7. The personal care composition of claim 6 comprising from 1 to 10% by weight of nanoemulsion.
PCT/KR2011/007162 2011-09-28 2011-09-28 Nanoemulsion containing a polyaspartic acid derivative and personal care composition containing same WO2013047923A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/KR2011/007162 WO2013047923A1 (en) 2011-09-28 2011-09-28 Nanoemulsion containing a polyaspartic acid derivative and personal care composition containing same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/KR2011/007162 WO2013047923A1 (en) 2011-09-28 2011-09-28 Nanoemulsion containing a polyaspartic acid derivative and personal care composition containing same

Publications (1)

Publication Number Publication Date
WO2013047923A1 true WO2013047923A1 (en) 2013-04-04

Family

ID=47995933

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2011/007162 WO2013047923A1 (en) 2011-09-28 2011-09-28 Nanoemulsion containing a polyaspartic acid derivative and personal care composition containing same

Country Status (1)

Country Link
WO (1) WO2013047923A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20200049150A (en) * 2018-10-31 2020-05-08 (주)아모레퍼시픽 Oil-in-water type cosmetic composition with a low viscosity comprising a high content of oil
CN115449074A (en) * 2022-09-02 2022-12-09 广州科罗德新材料科技有限公司 Polyasparagine derivative thickener with side chain containing linear alkyl chain and lysine

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080286364A1 (en) * 2007-05-16 2008-11-20 Fujifilm Corporation External dermatologic preparation
EP1997477A1 (en) * 2007-05-31 2008-12-03 FUJIFILM Corporation Anti-acne skin agent for external use
US20090004278A1 (en) * 2006-01-30 2009-01-01 Fujifilm Corporation Enzymatically Crosslinked Protein Nanoparticles
US20110117045A1 (en) * 2007-01-24 2011-05-19 Fujifilm Corporation Composition for hair

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090004278A1 (en) * 2006-01-30 2009-01-01 Fujifilm Corporation Enzymatically Crosslinked Protein Nanoparticles
US20110117045A1 (en) * 2007-01-24 2011-05-19 Fujifilm Corporation Composition for hair
US20080286364A1 (en) * 2007-05-16 2008-11-20 Fujifilm Corporation External dermatologic preparation
EP1997477A1 (en) * 2007-05-31 2008-12-03 FUJIFILM Corporation Anti-acne skin agent for external use

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20200049150A (en) * 2018-10-31 2020-05-08 (주)아모레퍼시픽 Oil-in-water type cosmetic composition with a low viscosity comprising a high content of oil
KR102575094B1 (en) 2018-10-31 2023-09-06 (주)아모레퍼시픽 Oil-in-water type cosmetic composition with a low viscosity comprising a high content of oil
CN115449074A (en) * 2022-09-02 2022-12-09 广州科罗德新材料科技有限公司 Polyasparagine derivative thickener with side chain containing linear alkyl chain and lysine
CN115449074B (en) * 2022-09-02 2023-10-20 广州科罗德新材料科技有限公司 Polyasparagine derivative thickener with side chain containing straight-chain alkyl chain and lysine

Similar Documents

Publication Publication Date Title
JP6219166B2 (en) Exopolysaccharides for the treatment and / or care of skin, mucous membranes, hair and / or nails
EP2579952B1 (en) Skin antiaging treatment
KR101988676B1 (en) Pgc-1alpha-modulating peptides
WO2011162478A2 (en) Cosmetic composition containing retinol stabilized by porous polymer beads and nanoemulsion
US9393260B2 (en) Exopolysaccharide for the treatment and/or care of the skin, mucous membranes and/or nails
KR101096868B1 (en) Skin preparation for external use
WO2018071640A1 (en) Compounds useful for the treatment and/or care of the skin, hair, nails and/or mucous membranes
KR20140043727A (en) Peptides useful in the treatment and/or care of the skin and/or mucous membranes and their use in cosmetic or pharmaceutical compositions
BR112020000123A2 (en) compound, use of a compound, cosmetic composition, and, method for non-therapeutic cosmetic care and / or treatment of skin, hair, nails and / or mucous membranes
CN116120402B (en) Cyclic peptide, and composition and application thereof
WO2017188622A1 (en) Anti-aging composition
CN115583988B (en) Synthetic peptides, compositions and uses thereof
CN114933631A (en) Peptide derivative isomer, and cosmetic composition or pharmaceutical composition and use thereof
CN110833514A (en) Polypeptide freeze-dried powder and application thereof in preparation of anti-aging cosmetics
WO2013047923A1 (en) Nanoemulsion containing a polyaspartic acid derivative and personal care composition containing same
KR101199966B1 (en) Nanoemulsion containing polyaspartic acid derivative and personal care composition comprising the same
WO2023085887A1 (en) Novel aptamer, and composition for cognitive function improvement and anti-aging comprising aptamer as active ingredient
CN116234554A (en) Methods and compositions for skin microbiome normalization of sensitive skin
CN1180845C (en) Melaninization inhibitor, skincare prepn., and bath agent
WO2016068393A1 (en) Liposome composition for treating acne, containing conjugate of lysophosphatidylcholine and chlorin e6
JP2004131401A (en) Skin cosmetic
EP4282399A1 (en) Cosmetic composition
JP2022163673A (en) Skin elasticity improver and external preparation for skin

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11872997

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 11872997

Country of ref document: EP

Kind code of ref document: A1