KR20120009848A - Nanoemulsion containing polyaspartic acid derivative and personal care composition comprising the same - Google Patents

Abstract

PURPOSE: A nanoemulsion containing polyaspartic derivative and a personal care composition containing the same are provided to induce collagen biosynthesis. CONSTITUTION: A nanoemulsion contains 1-20 weight parts of polyaspartic derivative, 1-5 weight parts of saturated lecithin, 1-10 weight parts of dissolution aid, 0.1-5 weight parts of lysolecithin, and 1-5 weight parts of sugar fatty acid ester surfactant. The polyaspartic acid derivative is prepared by substitution of lysine or lysine and C10-20 alkyl amine. The dissolution aid is ethanol. The sugar fatty acid ester surfactant is sugar stearic acid ester, sugar palmitic acid ester, sugar myristic acid ester, or sugar oleic acid ester. A personal care composition contains the nanoemulsion.

Description

NANOEMULSION CONTAINING POLYASPARTIC ACID DERIVATIVE AND PERSONAL CARE COMPOSITION COMPRISING THE SAME}

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.

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.

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.

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.

Also provided is a personal care composition comprising the nanoemulsion of the present invention.

Hereinafter, the present invention will be described in detail.

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.

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.

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.

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 the polyaspartic acid according to Scheme 1 below.

Scheme 1

In Scheme 1 R is -OH or C _{10 -20} alkyl amines, for example, n is 20 to 1,000, m is 20 to 1,500.

C _{10 -20} alkyl amines in the present invention, for example, decylamine (decylamine), dodecylamine (dodecylamine), pentadecyl amine (pentadecylamine), hexadecyl amine (hexadecylamine), heptadecyl amine (heptadecylamine), 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.

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.

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.

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.

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.

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.

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. As the 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 are not limited thereto. When 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 when 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.

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.

According to another aspect of the invention there is provided a personal care composition comprising the nanoemulsion of the invention.

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.

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.

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.

1 is a result of measuring the size of the particle diameter of the nanoemulsion of the present invention using Photal ELS-Z.
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 (TGF) -β)
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)
5 is a micrograph taken of mast cells to examine the anti-allergic effect.

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.

Manufacturing example  One: PASP - Lysine Manufacture

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”). .

Manufacturing example  2: PASP - HDA - Lysine Manufacture

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.

Example  One: PASP - Lysine Of nanoemulsion  Produce

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 degassed to obtain a nanoemulsion.

Example  2: PASP - HDA - Lysine Of nanoemulsion  Produce

Nanoemulsion was prepared in the same composition and method as Example 1 except for using PASP-HDA-Lysine instead of PASP-Lysine.

Example  3: body  Lotion

To prepare a body lotion using a nanoemulsion in the composition of Table 2.

Example  4: manufacture of shampoo

Shampoo was prepared using the nanoemulsion in the composition of Table 3 below.

Example  5: rinse preparation

To prepare a rinse using a nanoemulsion in the composition of Table 4.

Example  6: manufacture of cream

To prepare a cream using a nanoemulsion in the composition of Table 5.

Example  7: preparation of lotion

To prepare a lotion using a nanoemulsion in the composition of Table 6.

Example  8: Preparation of Essence

Essence was prepared using a nanoemulsion in the composition of Table 7 below.

Example  9: Skin  Produce

To prepare a skin using a nanoemulsion in the composition of Table 8.

Experimental Example  One: Of nanoemulsion  Particle distribution measurement

Particle distribution of the nanoemulsion prepared in Example 1 was measured using Photal ELS-Z and shown in FIG. 1. As a result of the measurement, the diameter size of the particles was found to be 50 to 200 nm.

Experimental Example  2: Nano Emulsion  Particle shooting

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.

Experimental Example  3: PASP - Lysine of Transdermal  Absorption Promotion Effect Experiment

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 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.

Column: C18 (4.6 × 200 mm, 5 μm)

Mobile phase: methanol

Flow rate: 0.8 ml / min

Detector: UV 275 nm

Experimental Example  4: collagen biosynthesis effect

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.

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.

Experimental Example  5: PASP - Lysine  And PASP - HDA - Lysine of MMP -1 inhibitory effect

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.

Experimental Example  6: using mast cells PASP - Lysine Of nanoemulsion  Antiallergic effect

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.

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.

Claims (7)

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 method of claim 1, wherein the polyaspartic acid derivative is one or more residues of a poly-aspartic acid-lysine, or lysine and C _{10 -20} nano-emulsion, characterized in that the substituted alkyl amine at the same time. 3. The method of claim 2, _-20 C ₁₀ alkyl amine is decyl amine, made dodecylamine, pentadecyl amine, hexadecyl amine, heptadecyl amine, and octadecyl nm, characterized in that at least one selected from the group consisting of amine emulsion. The nanoemulsion of claim 1 wherein said dissolution aid is ethanol. 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. A personal care composition comprising the nanoemulsion of claim 1. 7. The personal care composition of claim 6 comprising 1 to 10% by weight of nanoemulsion.

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