WO2011065772A2 - Water in oil type cosmetic composition for improving skin - Google Patents

Water in oil type cosmetic composition for improving skin Download PDF

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Publication number
WO2011065772A2
WO2011065772A2 PCT/KR2010/008428 KR2010008428W WO2011065772A2 WO 2011065772 A2 WO2011065772 A2 WO 2011065772A2 KR 2010008428 W KR2010008428 W KR 2010008428W WO 2011065772 A2 WO2011065772 A2 WO 2011065772A2
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WO
WIPO (PCT)
Prior art keywords
water
skin
cosmetic composition
ceramide
oil type
Prior art date
Application number
PCT/KR2010/008428
Other languages
French (fr)
Other versions
WO2011065772A3 (en
Inventor
Sang Hoon Jeon
Min Kyung Shim
Yeong Jin Choi
Original Assignee
Amorepacific Corporation
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 Amorepacific Corporation filed Critical Amorepacific Corporation
Priority to CN201080053269.6A priority Critical patent/CN102665658B/en
Publication of WO2011065772A2 publication Critical patent/WO2011065772A2/en
Publication of WO2011065772A3 publication Critical patent/WO2011065772A3/en

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/66Enzymes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/68Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin

Definitions

  • the stratum corneum is the outermost .layer of the skin, consisting of dead cells. Healthy skin has a turnover cycle of about 28 days, during which old keratin is removed and a layer of new cells is formed. However, if this turnover becomes slower due to internal and external factors, including aging, stress, UV rays and environmental pollution, unnecessary keratin will accumulate without being removed, so that the skin will become rough and thick, and melanin pigmentation will occur, thus making the skin black. In addition, this results in the formation of acne and wrinkles.
  • the epidermis that is the outermost layer of the skin is an organ which is always in contact with an external environment and serves as a protective barrier.
  • the skin barrier which is present in the horny layer of the skin serves to inhibit the loss of water and electrolytes, protect the human body from external damage and chemicals, and prevent bacteria and viruses from penetrating into the skin (Feingold KR. Cosmet . To i let .112:49-59, 1997).
  • the horny layer consists of two components: a protein consisting of dead kerat inocytes ; and a lipid present between kerat inocytes (Elias PM et al . Adv. Lipid Res. 24:1-26, 1991).
  • the lipid between kerat inocytes is believed to play the most important role in the maintenance of the skin barrier.
  • the lipid between kerat inocytes is a lipid mixture of ceramides, cholesterol, free fatty acids and the like and comprises the intercellular lamellae.
  • ceramides accounting for 40-50% of the hydrolipid film of the epidermis has a complex structure comprising sphingosine, amide- linked non-hydroxy acid, a -hydroxy acid, ⁇ -hydroxy acid or ester-linked fatty acid, and polarity formed by these structural factors is important in maintaining the lamellar structure of the hydrolipid film (Choi MJ et al. Am. J. Clin. Dermatol. 6:215-223, 2005).
  • the surface of the healthy skin of the human body is rich in nutrients required for the growth of microorganisms, and thus many bacteria normally live on the skin surface.
  • Such bacteria are broadly divided into pathogenic bacteria causing diseases in the human body, such as Staphylococcus or Streptococcus, and non-pathogenic bacteria causing no disease.
  • the non ⁇ pathogenic bacteria are also referred to as normal bacteria and found on a normal skin.
  • the non-pathogenic bacteria can be classified into two types: resident bacteria that are not removed even when friction is applied to the skin or even when a local disinfectant is administered to the skin; and transient bacteria that transiently live on the skin and are easily removed by local disinfection or the application of friction.
  • the present inventors have conducted many studies to find materials, which improve the skin to be smooth and keep the skin free from troubles.
  • the present inventors have found that the use of a ceramide-1 ike amino acid derivative together with a papain enzyme capsule and a polysaccharide can provides the immediate effects of improving the skin's horny layer and protecting the skin barrier and can selectively reduce bacteria that can cause skin troubles, among bacteria present in the skin, thereby completing the present invention.
  • the present invention provides a water-in- oil type cosmetic composition containing a ceramide-1 ike amino acid derivative, a papain enzyme capsule and a polysaccharide.
  • the water-in-oil type cosmetic composition of the present invention contains a buffer, having a structure similar to the phospholipid of the skin, in the outer phase of the cosmetic composition, and thus provides moisturization and suitable amounts of lipid components, which assist in skin lubrication.
  • the cosmetic composition of the present invention contains a capsule obtained by encapsulating protease for keratin removal, which is acceptable for cosmetic use, and thus the protease capsule exhibits no effect immediately after application, but can soften keratin at a given time after application and remove excess keratin upon cleaning of the cosmetic composition, thereby making the skin smooth.
  • the cosmetic composition of the present invention can selectively reduce the content of pathogenic bacteria compared to beneficial normal bacteria, and thus provide a long-term skin care effect.
  • the water-in-oil type cosmetic composition of the present invention makes the skin moist and smooth without keratin and keeps the skin free from troubles, thereby improving the skin to be easily applied with makeup.
  • FIG. 1 is a set of photographs showing the results of measuring the formulation stability of cosmetic compositions.
  • FIG. 2 shows the results of measuring the effects of the inventive cosmetic composition on the increase in water content and the decrease in the amount of keratin.
  • FIG. 3 is a set of photographs showing the results of measuring the amount of keratin on the skin with time after the use of the inventive cosmetic composition.
  • FIGS. 4 and 5 are a graph and photograph showing the results of measuring the irregularity of the facial surface using an image analyzer.
  • the present invention provides a water-in-oil type cosmetic composition containing a ceramide-1 ike amino acid derivative, a papain enzyme capsule and a polysaccharide.
  • the ceramide-1 ike amino acid derivative that is used as an active ingredient in the cosmetic composition of the present invention is phytosteryl/behenyl/octyldodecyl/lauroyl glutamate which is an emollient derived from glutamic acid, and is a paste-like material. It serves to prevent water from being lost from the skin and allows the skin to form a protective battier from the external environment.
  • the ceramide-1 ike amino acid derivative is melted and dispersed in the oil phase of the water-in-oil cosmetic composition.
  • the ceramide-1 ike amino acid derivative that is used in the present invention may be prepared according to any conventional method known in the art, and the preparation method is not specifically limited. For example, it may be synthesized using natural fatty acid, higher alcohol and phytosterol.
  • the ceramide-1 ike amino acid derivative that is used in the present invention is contained in an amount of 0.1-5.0 wt% based on the total weight of the composition. If the content of the ceramide-1 ike amino acid derivative is less than 0.1 wt%, the moisturizing effect of ceramide will be insignificant, and if the content is more than 5 wt%, it will make the composition sticky, thus giving a poor feel.
  • the papain enzyme that is used as an active ingredient in the inventive cosmetic composition is the juice of the fruit of Carica papaya and is a kind of protease.
  • This protease is known to assist in the treatment of inflammation and in blood circulation and have the effect of cleaning the skin or removing keratin without skin irritation.
  • a papain enzyme capsule is prepared by encapsulating the papain enzyme, and the prepared capsule is added to the oil phase of the water-in-oil cosmetic composition and dispersed in the formulat ion.
  • the papain enzyme capsule that is used in the present invention may be prepared according to any conventional method known in the art, and the preparation method is not specifically limited.
  • the papain enzyme capsule may be prepared by making a papain enzyme solution, containing the papain enzyme and a stabilizer, at the pH at which the papain enzyme is stable, mixing the papain enzyme solution with 1 iposome- forming components including lecithin, and passing the mixture through a high-pressure homogenizer.
  • the papain enzyme capsule is contained in an amount of 0.1-2.0 wt% based on the total weight of the composition. If the content of the papain enzyme capsule is less than 0.1 wt%, the keratin removing effect thereof will be insignificant, and if it is more than 2.0 wt%, it can give a poor feel upon application and cause skin irritation.
  • the polysaccharide that is used as an active ingredient in the cosmetic composition of the present invention has the prebiotic effect of Staphylococcus epidermidis and Prop i on i bacterium acnes.
  • a polysaccharide that may be used in the present invention is one or more selected from the group consisting of Orostachys japonicas polysaccharides, green tea polysaccharides and Artemisia capillaries polysaccharides.
  • the polysaccharide that is used in the present invention may be prepared according to any conventional method known in the art, and the preparation method is not specifically limited.
  • the polysaccharide may be prepared in the following manner. Orostachys japonicas, green tea or Artemisia capillaries is crushed, added to purified water, and heated and extracted at 95 ° C for 3 hours. The obtained extract is filtered sequentially through filters of 250 meshes, 3 rn, 1 urn and 0.5 ⁇ m, and the filtrate is evaporated by heating to 60 ° C , and then precipitated with 95% ethanol. The precipitate is centrifuged, and the resulting precipitate is dissolved in purified water. The solution is filtered sequentially through filters of 0.5 pm and 0.2 pm, and the filtrate is vacuum-dried, thereby obtaining a polysaccharide.
  • the polysaccharide that is used in the present invention is contained in an amount of 0.0001-1.0 wt% based on the total weight of the composition. If the content of the polysaccharide is less than 0.0001 wt%, the effect thereof cannot be expected, and if it is more than 1.0 wt%, it can cause skin irr itat ion.
  • the cosmetic composition of the present invention may be formulated in the form of makeup base, foundation, cream, lotion or concealer, but the formulation of the cosmetic composition is not specifically limited.
  • a solubilized ceramide material was prepared to consist of purified water, an emulsifier, a solubilizing agent and ceramide.
  • the ceramide was solubilized in an amount of 3-5 wt%.
  • Lipid technology is a key for the development of cosmetic products that can harmonize with the function of the skin.
  • a differentiated encapsulated material was prepared through accurate simulation of lipid structures in the skin and effective supply of active ingredients. Using a multilayer coating process with a fluidized bed technique, intercellular lamellae and lipid envelops were simultaneously realized.
  • the encapsulated ceramide material consisting of ceramide, lecithin and fatty acid was prepared using the multilayer coating process and added during the final process after the emulsi f icat ion of the formulation.
  • a capsule stabilization and softening process (at 45 ° C for 3 hours) was carried out to reduce the foreign body sensation of the encapsulated ceramide material.
  • the softening process was carried out in order to reduce the impurity content of the capsule and to allow oil to permeate into the capsule such that the capsule would naturally breaks.
  • the encapsulated ceramide material has advantages in that it is easily introduced into water-in-oil formulations compared to conventional solubilizing agents and in that it can increase moisturizing activity.
  • a ceramide-1 ike amino acid derivative was added to oil phase components and an emulsifier, and the mixture was melted by heating to 50 ⁇ 60 °C . Then, a flow control agent, a pigment and a papain enzyme capsule were added thereto and dispersed, thereby preparing an outer oil phase.
  • the inner water phase 2) was added to the outer oil phase 1), thereby obtaining a water-in-oil formulation.
  • the inner water phase 2) was added to the outer oil phase 1), thereby obtaining a water-in-oil formulation.
  • Test Example 2 Clinical test for skin moisturizing activity and amount of keratin
  • ⁇ 62> Specifically, after facial washing, the test subjects were adapted to constant temperature and constant humidity conditions (temperature: 22+ 2 ° C , and relative humidity: 40+2%) in a constant temperature and constant humidity chamber for 15 minutes, and then an optical photograph of a facial portion, the water content, the amount of keratin and the skin surface roughness were measured before application of the formulation. After the subjects had been adapted to the constant temperature and constant humidity conditions for about 15 minutes after application of the formulation, the above items were measured again. One week and two weeks after the formulation had been applied once a day, the above items were measured. After the measurement, a significant difference (paired t-test, PO.05) relative to the value obtained before application of the formulation was determined. Also, the irregularity of the facial surface was measured using an image analyzer. The results of the measurement are shown in FIGS. 2 to 5.
  • the cosmetic composition of the present invention when applied to the skin could increase the skin's water content, reduce the amount of keratin and the skin surface roughness, thereby making the skin smooth and moist.
  • Test Example 3 Experiment on effect of water-in-water formulation according to prebiotic content ⁇ 66>
  • a prebiotic material is a water-soluble material, and in the case of oil-in-water formulations, the outer phase is a water phase such that the active ingredient comes into contact with the skin. Thus, the effect of the formulation can be transferred, and the active ingredient in the water phase can be easily sampled during in vitro measurement.
  • the water phase is present in the inner phase, and thus it is difficult to predict the effect of the formulation. For this reason, an experiment on the effect of the water-in-oil formulation according to the content of the prebiotic material was carried out.
  • a ceramide-1 ike amino acid derivative was added to oil phase components and an emulsifier, and the mixture was melted by heating to 50 ⁇ 60 °C . Then, a flow control agent, a pigment and a papain enzyme capsule were added thereto and dispersed, thereby preparing an outer oil phase.
  • Water phase components including purified water and polyol , and a prebiot ic material, were mixed with each other in a separate container, thereby preparing an inner water phase.
  • the inner water phase 2) was added to the outer oil phase 1), thereby obtaining a water-in-oil formulation.
  • Examples 3 to 5 and Comparative Example 4 prepared as described above, was diluted 10-fold in distilled water. The dilution was stored in a water bath at 50 ° C for 5 minutes, and then vortexed five times for 1 minute each time. The vortexed solution was filtered through filter paper and then filtered through a 0.2-pm filter, thereby preparing sample filtrates.
  • ⁇ 74> 1 Each of the pretreated sample filtrates was dissolved by adding 1 wt% of peptone thereto, and then passed through 0.2-pm filter paper to disinfect the sample solution.
  • ⁇ 75> 2 Each of the disinfected sample solutions was inoculated with 10 ⁇ ml of a test bacterial solution, and then the initial cell count was determined.
  • the bacterial solution was suitably diluted with water, and then 1 ml of the dilution was plated on the medium surface, and the number of bacterial cells was calculated by multiplying the number of final colonies by the dilution fold).
  • Each of the cultured bacterial solutions was suitably diluted, and 1 ml of the dilution was taken.
  • the dilution of S. epidermidis was plated on TS agar, and then cultured at 35 ° C for 1 day, and the. dilution of P. acnes was plated on BHI agar and anaerobical ly cultured at 35 ° C for 3 days. Then, the number of cells in each bacterial solution was measured.
  • Rate of increase in number of bacterial cells in sample number of bacterial cells in sample after 24 hours/ number of bacterial cells in sample after 0 hour ⁇ number of bacterial cells in blank after 24 hours /number of bacterial cells in blank after 0 hour
  • K rate of increase of S. epidermidis in sample / rate of increase of
  • the water-in-oil cosmetic composition of the present invention has an excellent prebiotic effect, and thus can selectively reduce the content of pathogenic bacteria relative to beneficial normal bacteria. Accordingly, it can suppress skin troubles and has a long-term skin care effect .

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Abstract

The present invention relates to a water-in-oil type cosmetic composition, which improves the skin to be smooth and keeps the skin free from troubles, and more particularly to a water-in-oil cosmetic composition which has a short-term skin improvement effect, caused by a ceramide-like amino acid derivative and a stabilized papain enzyme, and a long-term skin improvement effect caused by a polysaccharide having a prebiotic effect of selectively controlling bacteria.

Description

[DESCRIPTION]
[Invention Title]
WATER IN OIL TYPE COSMETIC COMPOSITION FOR IMPROVING SKIN
[Technical Field]
<i> The present invention relates to a water-in-oil type cosmetic composition, which improves the skin to be smooth and keeps the skin free from troubles, and more particularly to a water-in-oil type cosmetic composition which has a short-term skin improvement effect, caused by a ceramide-1 ike amino acid derivative and a stabilized papain enzyme, and a long-term skin improvement effect caused by a polysaccharide having a prebiotic effect of selectively controlling bacteria.
[Background Art]
<2> The stratum corneum is the outermost .layer of the skin, consisting of dead cells. Healthy skin has a turnover cycle of about 28 days, during which old keratin is removed and a layer of new cells is formed. However, if this turnover becomes slower due to internal and external factors, including aging, stress, UV rays and environmental pollution, unnecessary keratin will accumulate without being removed, so that the skin will become rough and thick, and melanin pigmentation will occur, thus making the skin black. In addition, this results in the formation of acne and wrinkles.
<3> The epidermis that is the outermost layer of the skin is an organ which is always in contact with an external environment and serves as a protective barrier. The skin barrier which is present in the horny layer of the skin serves to inhibit the loss of water and electrolytes, protect the human body from external damage and chemicals, and prevent bacteria and viruses from penetrating into the skin (Feingold KR. Cosmet . To i let .112:49-59, 1997). The horny layer consists of two components: a protein consisting of dead kerat inocytes ; and a lipid present between kerat inocytes (Elias PM et al . Adv. Lipid Res. 24:1-26, 1991). Among them, the lipid between kerat inocytes is believed to play the most important role in the maintenance of the skin barrier. The lipid between kerat inocytes is a lipid mixture of ceramides, cholesterol, free fatty acids and the like and comprises the intercellular lamellae. Particularly, ceramides accounting for 40-50% of the hydrolipid film of the epidermis has a complex structure comprising sphingosine, amide- linked non-hydroxy acid, a -hydroxy acid, ω -hydroxy acid or ester-linked fatty acid, and polarity formed by these structural factors is important in maintaining the lamellar structure of the hydrolipid film (Choi MJ et al. Am. J. Clin. Dermatol. 6:215-223, 2005).
<4> The surface of the healthy skin of the human body is rich in nutrients required for the growth of microorganisms, and thus many bacteria normally live on the skin surface. Such bacteria are broadly divided into pathogenic bacteria causing diseases in the human body, such as Staphylococcus or Streptococcus, and non-pathogenic bacteria causing no disease. The non¬ pathogenic bacteria are also referred to as normal bacteria and found on a normal skin. The non-pathogenic bacteria can be classified into two types: resident bacteria that are not removed even when friction is applied to the skin or even when a local disinfectant is administered to the skin; and transient bacteria that transiently live on the skin and are easily removed by local disinfection or the application of friction.
<5> Normal bacteria living on the skin usually serve to restrain other pathogenic bacteria from causing diseases when they enter the skin. Thus, normal bacteria living on the skin are highly beneficial to the human body and are necessary for the human body. If the skin is damaged or if the number of non-pathogenic bacteria decreases or if the number of pathogenic bacteria rapidly increases, disease will occur in the human body. Thus, it is considered that, if bacteria living on the skin are controlled such that the increase rate of non-pathogenic normal bacteria is higher than that of pathogenic bacteria, skin conditions can be improved.
[Disclosure]
[Technical Problem]
<6> Accordingly, the present inventors have conducted many studies to find materials, which improve the skin to be smooth and keep the skin free from troubles. As a result, the present inventors have found that the use of a ceramide-1 ike amino acid derivative together with a papain enzyme capsule and a polysaccharide can provides the immediate effects of improving the skin's horny layer and protecting the skin barrier and can selectively reduce bacteria that can cause skin troubles, among bacteria present in the skin, thereby completing the present invention.
<7> It is, therefore, an object of the present invention to provide a water-in-oil type cosmetic composition which improves the skin to be smooth and keeps the skin free from troubles.
[Technical Solution]
<8> To achieve the above object, the present invention provides a water-in- oil type cosmetic composition containing a ceramide-1 ike amino acid derivative, a papain enzyme capsule and a polysaccharide.
[Advantageous Effects]
<9> The water-in-oil type cosmetic composition of the present invention contains a buffer, having a structure similar to the phospholipid of the skin, in the outer phase of the cosmetic composition, and thus provides moisturization and suitable amounts of lipid components, which assist in skin lubrication. Also, the cosmetic composition of the present invention contains a capsule obtained by encapsulating protease for keratin removal, which is acceptable for cosmetic use, and thus the protease capsule exhibits no effect immediately after application, but can soften keratin at a given time after application and remove excess keratin upon cleaning of the cosmetic composition, thereby making the skin smooth. In addition, the cosmetic composition of the present invention can selectively reduce the content of pathogenic bacteria compared to beneficial normal bacteria, and thus provide a long-term skin care effect. Ultimately, the water-in-oil type cosmetic composition of the present invention makes the skin moist and smooth without keratin and keeps the skin free from troubles, thereby improving the skin to be easily applied with makeup.
[Description of Drawings]
<io> FIG. 1 is a set of photographs showing the results of measuring the formulation stability of cosmetic compositions.
<ii> FIG. 2 shows the results of measuring the effects of the inventive cosmetic composition on the increase in water content and the decrease in the amount of keratin.
<12> FIG. 3 is a set of photographs showing the results of measuring the amount of keratin on the skin with time after the use of the inventive cosmetic composition.
<i3> FIGS. 4 and 5 are a graph and photograph showing the results of measuring the irregularity of the facial surface using an image analyzer.
[Best Mode]
<14> The present invention provides a water-in-oil type cosmetic composition containing a ceramide-1 ike amino acid derivative, a papain enzyme capsule and a polysaccharide.
<I5> Hereinafter, the present invention will be described in further detail.
<16> The ceramide-1 ike amino acid derivative that is used as an active ingredient in the cosmetic composition of the present invention is phytosteryl/behenyl/octyldodecyl/lauroyl glutamate which is an emollient derived from glutamic acid, and is a paste-like material. It serves to prevent water from being lost from the skin and allows the skin to form a protective battier from the external environment. The ceramide-1 ike amino acid derivative is melted and dispersed in the oil phase of the water-in-oil cosmetic composition.
<i7> The ceramide-1 ike amino acid derivative that is used in the present invention may be prepared according to any conventional method known in the art, and the preparation method is not specifically limited. For example, it may be synthesized using natural fatty acid, higher alcohol and phytosterol.
<i8> The ceramide-1 ike amino acid derivative that is used in the present invention is contained in an amount of 0.1-5.0 wt% based on the total weight of the composition. If the content of the ceramide-1 ike amino acid derivative is less than 0.1 wt%, the moisturizing effect of ceramide will be insignificant, and if the content is more than 5 wt%, it will make the composition sticky, thus giving a poor feel.
<i9> The papain enzyme that is used as an active ingredient in the inventive cosmetic composition is the juice of the fruit of Carica papaya and is a kind of protease. This protease is known to assist in the treatment of inflammation and in blood circulation and have the effect of cleaning the skin or removing keratin without skin irritation.
<20> Generally, in cosmetic formulations containing various oil components, which can destroy the three-dimensional structure of enzymes, together with an emulsifier, the technology capable of introducing the enzymes into the cosmetic formulations is required, because the enzymes can be immediately activated. In the present invention, a papain enzyme capsule is prepared by encapsulating the papain enzyme, and the prepared capsule is added to the oil phase of the water-in-oil cosmetic composition and dispersed in the formulat ion.
<2i> The papain enzyme capsule that is used in the present invention may be prepared according to any conventional method known in the art, and the preparation method is not specifically limited. For example, the papain enzyme capsule may be prepared by making a papain enzyme solution, containing the papain enzyme and a stabilizer, at the pH at which the papain enzyme is stable, mixing the papain enzyme solution with 1 iposome- forming components including lecithin, and passing the mixture through a high-pressure homogenizer.
<22> The papain enzyme capsule is contained in an amount of 0.1-2.0 wt% based on the total weight of the composition. If the content of the papain enzyme capsule is less than 0.1 wt%, the keratin removing effect thereof will be insignificant, and if it is more than 2.0 wt%, it can give a poor feel upon application and cause skin irritation.
<23> The polysaccharide that is used as an active ingredient in the cosmetic composition of the present invention has the prebiotic effect of Staphylococcus epidermidis and Prop i on i bacterium acnes.
<24> A polysaccharide that may be used in the present invention is one or more selected from the group consisting of Orostachys japonicas polysaccharides, green tea polysaccharides and Artemisia capillaries polysaccharides.
<25> The polysaccharide that is used in the present invention may be prepared according to any conventional method known in the art, and the preparation method is not specifically limited. For example, the polysaccharide may be prepared in the following manner. Orostachys japonicas, green tea or Artemisia capillaries is crushed, added to purified water, and heated and extracted at 95 °C for 3 hours. The obtained extract is filtered sequentially through filters of 250 meshes, 3 rn, 1 urn and 0.5 μ m, and the filtrate is evaporated by heating to 60 °C , and then precipitated with 95% ethanol. The precipitate is centrifuged, and the resulting precipitate is dissolved in purified water. The solution is filtered sequentially through filters of 0.5 pm and 0.2 pm, and the filtrate is vacuum-dried, thereby obtaining a polysaccharide.
<26> The polysaccharide that is used in the present invention is contained in an amount of 0.0001-1.0 wt% based on the total weight of the composition. If the content of the polysaccharide is less than 0.0001 wt%, the effect thereof cannot be expected, and if it is more than 1.0 wt%, it can cause skin irr itat ion.
<27> The cosmetic composition of the present invention may be formulated in the form of makeup base, foundation, cream, lotion or concealer, but the formulation of the cosmetic composition is not specifically limited.
[Mode for Invention]
<28> Hereinafter, the present invention will be described in further detail with reference to examples and test examples, but the scope of the present invention is not limited only to these examples.
<29> Preparation Example 1: Solubilized ceramide material
<30> A solubilized ceramide material was prepared to consist of purified water, an emulsifier, a solubilizing agent and ceramide. Herein, the ceramide was solubilized in an amount of 3-5 wt%.
<3i> Preparation Example 2- Encapsulated ceramide material
<32> Lipid technology is a key for the development of cosmetic products that can harmonize with the function of the skin. A differentiated encapsulated material was prepared through accurate simulation of lipid structures in the skin and effective supply of active ingredients. Using a multilayer coating process with a fluidized bed technique, intercellular lamellae and lipid envelops were simultaneously realized.
<33> The encapsulated ceramide material consisting of ceramide, lecithin and fatty acid was prepared using the multilayer coating process and added during the final process after the emulsi f icat ion of the formulation. A capsule stabilization and softening process (at 45 °C for 3 hours) was carried out to reduce the foreign body sensation of the encapsulated ceramide material. The softening process was carried out in order to reduce the impurity content of the capsule and to allow oil to permeate into the capsule such that the capsule would naturally breaks. The encapsulated ceramide material has advantages in that it is easily introduced into water-in-oil formulations compared to conventional solubilizing agents and in that it can increase moisturizing activity.
<34>
<35> Examples 1 and 2 and Comparative Examples 1 to 3
<36> According to the components and contents shown in Table 1 below, formulations of Examples 1 and 2 and Comparative Examples 1 to 3 were prepared (unit-' wt ). In Table 1, the ceramide-1 ike amino acid derivative was phytosteryl/behenyl/octyldodecyl/lauroyl glutamate (CAS No .245443-09-8 ; purchased from Ajinomoto Co., Inc.).
<37> [Table 1]
Figure imgf000009_0001
<38>
<39> <Method for preparing formulations of Examples 1 and 2>
<40> 1) A ceramide-1 ike amino acid derivative was added to oil phase components and an emulsifier, and the mixture was melted by heating to 50~60 °C . Then, a flow control agent, a pigment and a papain enzyme capsule were added thereto and dispersed, thereby preparing an outer oil phase.
<4i> 2) Water-phase components, including purified water and polyol, were mixed with each other in a separate container, thus preparing an inner water phase .
<42> 3) The inner water phase 2) was added to the outer oil phase 1), thereby obtaining a water-in-oil formulation.
<43> <Method for preparing formulation of Comparative Example 1>
<44> 1) Oil phase components and an emulsifier were melted by heating to
50-60 °C , and then a flow control agent and a pigment were added thereto and dispersed, thereby preparing an outer oil phase.
<45> 2) Water-phase components, including purified water and polyol, were mixed with each other in a separate container, and then a solubilized ceramide material was added thereto, thereby preparing an inner water phase. <46> 3) The inner water phase 2) was added to the outer oil phase 1), thereby obtaining a water-in-oil formulation.
<47> <Method for preparing formulation of Comparative Example 2>
<48> 1) Oil phase components and an emulsifier were melted by heating to
50-60 °C , and then a flow control agent and a pigment were added thereto and dispersed, thereby preparing an outer oil phase.
<49> 2) Water phase components, including purified water and polyol, were mixed with each other, thereby preparing an inner water phase.
<50> 3) The inner water phase 2) was added to the outer oil phase 1), thereby obtaining a water-in-oil formulation.
<5i> 4) An encapsulated ceramide material was added to the water-in-oil formulation 3) and uniformly dispersed using an Agi-mixer.
<52>
<53> Test Example 1: Evaluation of water-in-oil formulation according to kind of ceramide
<54> In order evaluate the formulation stability according to the kind of ceramide, the formulations of Examples 1 and 2 and Comparative Examples 1 to 3 were measured for temperature stability in a constant temperature chamber and for stability according to temperature changes in a cyclic chamber. The temperature stability in the constant temperature chamber was measured at room temperature, 30 °C , 45 °C and 55 °C at the same time everyday, and one stable for 7 days was used as a standard. The stability in the cyclic chamber was measured for 7 days under a shaking condition of 170 rpm on the basis of one cycle/day at a temperature change stage of 1 hour while maintaining each sample for 7 hours at each of -10 °C , 30 °C and 45 °C . The results of the measurement are shown in Table 2 below.
<55> The formulation stability was determined by apparently observing emulsion stability and pigment dispersabi 1 ity five times in total for 7 days. The evaluation was performed based on the following criteria: 0 = stable in the observation of all five times; Δ= stable in the observation of 3-4 times; and X= stable in the observation of two times or less.
<56> [Table 2]
Figure imgf000011_0001
<57>
<58> As can be seen in FIG. 1 and Table 2, the materials other than the ceramide-1 ike amino acid derivative that is the oil phase material had poor stability. It could be seen that, in the formulation of Comparative Example 1 containing the solubilized ceramide material, oil was gradually separated from the formulation within several hours after emulsif ication. Also, the formulation of Comparative Example 2 containing the ceramide capsule material had a problem in that the capsule breaks by swelling at 55 °C before it is not transferred to customers. In addition, in the case of Comparative Example 2, when the capsule was uniformly dispersed in the formulation, it was present in an opaque layer to give a foreign body sensation, unlike a basic product. On the other hand, the ceramide-1 ike amino acid derivative could be introduced in the form of a paste into the oil phase components, and thus it could be easily introduced into the formulation and did not affect the formulation stability, suggesting that the formulations of Examples 1 and 2 had excellent stability.
<59>
<60> Test Example 2: Clinical test for skin moisturizing activity and amount of keratin
<6i> In order to confirm the effect of improving the skin to be smooth, the skin moisturizing activity of the formulation of Example 2 and the amount of keratin before and after application of the formulation to the skin were clinically measured. The measurements were conducted on a total of 10 persons for 2 weeks. The papain enzyme used in this experiment was purchased from AT Lab. Co. , Ltd.
<62> Specifically, after facial washing, the test subjects were adapted to constant temperature and constant humidity conditions (temperature: 22+ 2 °C , and relative humidity: 40+2%) in a constant temperature and constant humidity chamber for 15 minutes, and then an optical photograph of a facial portion, the water content, the amount of keratin and the skin surface roughness were measured before application of the formulation. After the subjects had been adapted to the constant temperature and constant humidity conditions for about 15 minutes after application of the formulation, the above items were measured again. One week and two weeks after the formulation had been applied once a day, the above items were measured. After the measurement, a significant difference (paired t-test, PO.05) relative to the value obtained before application of the formulation was determined. Also, the irregularity of the facial surface was measured using an image analyzer. The results of the measurement are shown in FIGS. 2 to 5.
<63> As can be seen in FIGS. 2 to 5, the cosmetic composition of the present invention when applied to the skin could increase the skin's water content, reduce the amount of keratin and the skin surface roughness, thereby making the skin smooth and moist.
<64>
<65> Test Example 3: Experiment on effect of water-in-water formulation according to prebiotic content <66> A prebiotic material is a water-soluble material, and in the case of oil-in-water formulations, the outer phase is a water phase such that the active ingredient comes into contact with the skin. Thus, the effect of the formulation can be transferred, and the active ingredient in the water phase can be easily sampled during in vitro measurement. On the other hand, in the case of water-in-oil formulations as described in the present invention, the water phase is present in the inner phase, and thus it is difficult to predict the effect of the formulation. For this reason, an experiment on the effect of the water-in-oil formulation according to the content of the prebiotic material was carried out. Foundation formulations of Comparative Example 4 and Examples 3 to 5, each having the composition shown in Table 3 below, were prepared. Herein, a polysaccharide was added to the water part of the foundation formulation in amounts of 0, 2, 0.1 and 0.005 wt%. The polysaccharide that is the prebiotic material was obtained by green tea, Artemisia capillaries and Orostachys japonicas polysaccharides at a weight ratio of 60:30:10 wt%, and each of the polysaccharides used herein was purchased from Bio-Land Co., Ltd., Korea.
<67> [Table 3]
Figure imgf000014_0001
<68> <Methods for preparing formulations of Examples 3 to 5 and Comparative
Example 4>
<69> 1) A ceramide-1 ike amino acid derivative was added to oil phase components and an emulsifier, and the mixture was melted by heating to 50~60 °C . Then, a flow control agent, a pigment and a papain enzyme capsule were added thereto and dispersed, thereby preparing an outer oil phase.
<70> 2) Water phase components, including purified water and polyol , and a prebiot ic material, were mixed with each other in a separate container, thereby preparing an inner water phase.
<7i> 3) The inner water phase 2) was added to the outer oil phase 1), thereby obtaining a water-in-oil formulation.
<72> In the experiment, each of the water-in-oil foundation formulations of
Examples 3 to 5 and Comparative Example 4, prepared as described above, was diluted 10-fold in distilled water. The dilution was stored in a water bath at 50 °C for 5 minutes, and then vortexed five times for 1 minute each time. The vortexed solution was filtered through filter paper and then filtered through a 0.2-pm filter, thereby preparing sample filtrates.
<73> <Bacterial cell count method>
<74> 1. Each of the pretreated sample filtrates was dissolved by adding 1 wt% of peptone thereto, and then passed through 0.2-pm filter paper to disinfect the sample solution.
<75> 2. Each of the disinfected sample solutions was inoculated with 10 μΙΙ ml of a test bacterial solution, and then the initial cell count was determined. (Herein, the bacterial solution was suitably diluted with water, and then 1 ml of the dilution was plated on the medium surface, and the number of bacterial cells was calculated by multiplying the number of final colonies by the dilution fold).
<76> 3. Each of the sample solutions inoculated with the bacterial solution was shake-cultured at 32 °C for 1 day in the case of S. epidermidis and anaerobical ly cultured at 35 °C for 1 day in the case of P. acnes.
<77> 4. Each of the cultured bacterial solutions was suitably diluted, and 1 ml of the dilution was taken. The dilution of S. epidermidis was plated on TS agar, and then cultured at 35 °C for 1 day, and the. dilution of P. acnes was plated on BHI agar and anaerobical ly cultured at 35 °C for 3 days. Then, the number of cells in each bacterial solution was measured.
<78> The number of bacterial cells was measured according to the above- described cell count method, and the rate of increase in the number of bacterial cells in each sample was calculated according to the following equation 1. The results of the calculation are shown in Table 4 below.
<79> [Equation 1] <80> Rate of increase in number of bacterial cells in sample = number of bacterial cells in sample after 24 hours/ number of bacterial cells in sample after 0 hour ÷ number of bacterial cells in blank after 24 hours /number of bacterial cells in blank after 0 hour
<8i> The K value for comparing the rate of increase of S. epidermidis in the sample with the rate of increase of P. acnes in the sample was calculated according to the following equation according to the following equation 2. A higher K value indicates that the rate of increase of beneficial bacteria relatively increases to provide a prebiotic effect.
<82> [Equation 2]
<83> K = rate of increase of S. epidermidis in sample / rate of increase of
P. acnes in sample
<84> [Table 4]
Figure imgf000016_0001
<85> As can be seen in Table 4 above, the polysaccharide in the formulations of Examples 3 to 5 had prebiotic effects which were substantially similar over the content range of 0.2-0.0005 wt%, when considered that it was 10-fold diluted in the pretreatment step. Thus, it could be found that, even when the polysaccharide was added to the water-in-oil type cosmetic composition in an amount of only 0.0005 wt , it could exhibit a prebiotic effect.
<86> Therefore, the water-in-oil cosmetic composition of the present invention has an excellent prebiotic effect, and thus can selectively reduce the content of pathogenic bacteria relative to beneficial normal bacteria. Accordingly, it can suppress skin troubles and has a long-term skin care effect .
<87> While the present invention has been described with reference to the particular illustrative embodiments, it is not to be restricted by the embodiments but only by the appended claims. It is to be appreciated that those skilled in the art can change or modify the embodiments without departing from the scope and spirit of the present invention.

Claims

[CLAIMS]
[Claim 1]
A water— in-oil type cosmetic composition containing a ceramide-1 ike amino acid derivative, a papain enzyme capsule and a polysaccharide.
[Claim 2]
The water-in-oil type cosmetic composition of Claim 1, wherein the ceramide-1 ike amino acid derivative is phytosteryl/behenyl/octyldodecyl/lauroyl glutamate.
[Claim 3]
The water-in-oil type cosmetic composition of Claim 1, wherein the ceramide-1 ike amino acid derivative is contained in an amount of 0.1-5.0 wt based on the total weight of the composition.
[Claim 4]
The water-in-oil type cosmetic composition of Claim 1, wherein the papain enzyme capsule is contained in an amount of 0.1-2.0 wt% based on the total weight of the composition.
[Claim 5]
The water-in-oil type cosmetic composition of Claim 1, wherein the polysaccharide is at least one selected from the group consisting of Orostachys japonicas polysaccharides, green tea polysaccharides and Artemisia capillaries polysaccharides.
[Claim 6]
The water-in-oil type cosmetic composition of Claim 1, wherein the polysaccharide is contained in an amount of 0.0001-1.0 wt% based on the total weight of the composition.
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013122931A3 (en) * 2012-02-14 2014-03-13 The Procter & Gamble Company Topical use of a skin-commensal prebiotic agent and compositions containing the same
US8815538B2 (en) 2011-11-08 2014-08-26 The Procter & Gamble Company Method of making cosmetic compositions containing a prebiotic
EP2873413A4 (en) * 2012-07-10 2015-08-12 Shiseido Co Ltd Water-in-oil emulsion cosmetic
US10639267B2 (en) 2015-09-02 2020-05-05 Amorepacific Corporation High internal phase water-in-oil type cosmetic composition
US10806769B2 (en) 2016-03-31 2020-10-20 Gojo Industries, Inc. Antimicrobial peptide stimulating cleansing composition
US10874700B2 (en) 2016-03-31 2020-12-29 Gojo Industries, Inc. Sanitizer composition with probiotic/prebiotic active ingredient
US11564879B2 (en) 2016-11-23 2023-01-31 Gojo Industries, Inc. Sanitizer composition with probiotic/prebiotic active ingredient

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105640819A (en) * 2014-11-13 2016-06-08 广州十长生化妆品有限公司 Skin tendering smoothening whitening exfoliating microsphere and application thereof
KR101908347B1 (en) * 2014-12-31 2018-10-17 (주)아모레퍼시픽 Chemically anisotropic particles and w/o emulsion composition comprising the same
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CN111675770B (en) * 2020-07-15 2022-03-15 延边大学 Preparation method and application of orostachys wolfsii polysaccharide

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5834013A (en) * 1994-06-08 1998-11-10 L'oreal Cosmetic or dermatological composition in the form of an aqueous and stable dispersion of cubic gel particles based on phytanetriol and containing a surface-active agent which has a fatty chain, as dispersing and stabilizing agent
US20060198800A1 (en) * 2003-08-14 2006-09-07 Natalie Dilallo Skin care compositions including hexapeptide complexes and methods of their manufacture
US20060246029A1 (en) * 2005-03-16 2006-11-02 Procyte Corporation Methods and compositions for preventing and treating aging or photodamaged skin

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006028109A (en) * 2004-07-20 2006-02-02 Kao Corp Oil-in-water type emulsifying composition
JP4696507B2 (en) * 2004-09-13 2011-06-08 味の素株式会社 Cleaning composition
JP5207426B2 (en) * 2006-06-30 2013-06-12 学校法人神奈川大学 Cosmetics and method for producing the same
JP5666763B2 (en) * 2007-04-11 2015-02-12 味の素株式会社 Water-in-oil emulsion composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5834013A (en) * 1994-06-08 1998-11-10 L'oreal Cosmetic or dermatological composition in the form of an aqueous and stable dispersion of cubic gel particles based on phytanetriol and containing a surface-active agent which has a fatty chain, as dispersing and stabilizing agent
US20060198800A1 (en) * 2003-08-14 2006-09-07 Natalie Dilallo Skin care compositions including hexapeptide complexes and methods of their manufacture
US20060246029A1 (en) * 2005-03-16 2006-11-02 Procyte Corporation Methods and compositions for preventing and treating aging or photodamaged skin

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
E. BERARDESCA ET AL.: 'Effects of topical gluco-oligosaccharide and collagen tripeptide F in the treatment of sensitive atopic skin.' INTERNATIONAL JOURNAL OF COSMETIC SCIENCE vol. 31, no. 4, August 2009, pages 271 - 277 *

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8815538B2 (en) 2011-11-08 2014-08-26 The Procter & Gamble Company Method of making cosmetic compositions containing a prebiotic
US9289376B2 (en) 2011-11-08 2016-03-22 The Procter & Gamble Company Method of identifying prebiotics and compositions containing the same
US9271924B2 (en) 2011-11-08 2016-03-01 The Procter & Gamble Company Method of identifying prebiotics and compositions containing the same
WO2013122931A3 (en) * 2012-02-14 2014-03-13 The Procter & Gamble Company Topical use of a skin-commensal prebiotic agent and compositions containing the same
WO2013122932A3 (en) * 2012-02-14 2014-08-07 The Procter & Gamble Company Topical use of a skin-commensal prebiotic agent and compositions containing the same
CN104105470A (en) * 2012-02-14 2014-10-15 宝洁公司 Topical use of a skin-commensal prebiotic agent and compositions containing the same
JP2015507011A (en) * 2012-02-14 2015-03-05 ザ プロクター アンド ギャンブルカンパニー Topical use of skin symbiotic prebiotics and compositions containing them
JP2015507012A (en) * 2012-02-14 2015-03-05 ザ プロクター アンド ギャンブルカンパニー Topical use of skin symbiotic prebiotics and compositions containing them
RU2576613C1 (en) * 2012-07-10 2016-03-10 Шисейдо Компани, Лтд. Cosmetic emulsion of water-in-oil type
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US10639267B2 (en) 2015-09-02 2020-05-05 Amorepacific Corporation High internal phase water-in-oil type cosmetic composition
US10806769B2 (en) 2016-03-31 2020-10-20 Gojo Industries, Inc. Antimicrobial peptide stimulating cleansing composition
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US11998575B2 (en) 2016-03-31 2024-06-04 Gojo Industries, Inc. Sanitizer composition with probiotic/prebiotic active ingredient
US11564879B2 (en) 2016-11-23 2023-01-31 Gojo Industries, Inc. Sanitizer composition with probiotic/prebiotic active ingredient

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