JP2007031381A - Ceramide-containing emulsion composition and method for producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a ceramide-containing emulsion composition that suppresses precipitation of ceramide crystal and is used in cosmetics requiring wide sensuality. <P>SOLUTION: The ceramide-containing emulsion composition is obtained by emulsifying a mixture comprising ceramide as a component (a), an esterified product of glycerin, a 8-30C fatty acid and an aliphatic saturated dibasic acid as a component (b), a polyglycerin fatty acid ester as a component (c), an oil as a component (d) and a polyhydric alcohol as a component (e) under 500-2,000 kg/cm<SP>2</SP>pressure. Especially the polyhydric alcohol is glycerin. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a ceramide-containing emulsion composition and a method for producing the same, and in particular, contains a ceramide having a high moisturizing property and is excellent in terms of functional properties such as stability over time and moist feeling, and can be used as a cosmetic or medical product. The present invention relates to a composition and a method for producing the composition.

Ceramide is a sphingosine fatty acid amide bond and is an important component of intercellular lipids. It is highly moisturizing, that is, has a high water retention ability, and is a very useful substance for protecting the stratum corneum of skin. In addition, it is a substance that is expected to improve skin changes, immune functions, and allergic diseases associated with aging. For this reason, cosmetics and external preparations containing ceramide for protecting the skin from various external factors are used regardless of age and gender.
However, since ceramide is difficult to dissolve in water and oil, it is difficult to formulate it into cosmetics or external preparations. For this reason, a method for emulsifying ceramide has been developed.
For example, a microfluidizer comprising an aqueous component containing colloidal hydrous silicate, polyethylene glycol and ceramide, and at least one oily component selected from the group consisting of squalane, fatty acid triglycerides, waxes, higher alcohols and higher fatty acids The method of emulsifying by this is known (Patent Document 1).
In addition, a method is known in which ceramides, alkylyl lactic acid and / or a salt thereof, and glycerin and / or a polyglycerin fatty acid ester having a polymerization degree of 2 or more are blended (Patent Document 2).
A method of blending ceramides with sorbitan monolaurate is known (Patent Document 3).
On the other hand, glycerin or its condensate and direct carbon number 2 to 28 are used as a gelling agent that forms an organic liquid such as alcohols, esters, and hydrocarbons that are liquid at room temperature to form a gel-like solid by adding a small amount. An esterification product of a chain saturated fatty acid and an aliphatic saturated dibasic acid having 12 to 28 carbon atoms is known (Patent Document 4).

However, the conventional technique has a problem that the precipitation of ceramide crystals cannot be completely suppressed. In particular, there is a limit in maintaining the suppression of ceramide crystal precipitation not only during the production but also after the post-production time. Cosmetics and medical products have long-term stability under various environments, considering the period and environment in which they are manufactured and delivered to consumers, and when they are actually opened and used. Desired. In addition, ceramide-containing products made by conventional techniques are inferior due to their limited sensory characteristics such as lack of moistness and stickiness when actually used.
Japanese Patent Application Laid-Open No. 08-217666 JP 2001-199872 A Japanese Patent Laying-Open No. 2005-8580 Japanese Patent No. 2700377

  The present invention has been made in order to cope with such problems, and an object of the present invention is to provide a ceramide-containing emulsion composition capable of suppressing the precipitation of ceramide crystals and obtaining a preparation having excellent stability. . In addition, it can be used for cosmetics that require a wide range of sensuality, such as lotion and other moisturizing elements that moisturize the skin while having a transparent and dry feeling like lotion. The object is to provide a ceramide-containing emulsion composition.

In order to achieve the above-mentioned problems, the present inventors have intensively studied. As a result, by emulsifying a mixture containing ceramide and a predetermined glycerin derivative at a pressure of 500 to 2000 kg / cm ² , the precipitation of ceramide crystals is suppressed, It was also found that a stable ceramide-containing emulsion composition can be obtained.
That is, the ceramide-containing emulsion composition of the present invention comprises a mixture containing the following component (a), component (b), component (c), component (d) and component (e) at a pressure of 500 to 2000 kg / cm ² . It is obtained by emulsifying with
Component (a) is ceramide, Component (b) is an esterification product of glycerin, a fatty acid having 8 to 30 carbon atoms and an aliphatic saturated dibasic acid, and Component (c) is a polyglycerol fatty acid ester. Component (d) is oil and component (e) is a polyhydric alcohol.
Moreover, the polyhydric alcohol of the said component (e) is glycerol.

The method for producing a ceramide-containing emulsion composition of the present invention comprises a compound containing component (a), component (b), and component (d), and a compound containing component (c) and component (e). After mixing to obtain a mixture, the mixture is emulsified at a pressure of 500 to 2000 kg / cm ² .
Further, the emulsified product obtained by the above method is mixed with water and stirred.

  Since the ceramide-containing emulsion composition of the present invention is high-pressure emulsified with ceramide and glycerin derivatives, precipitation of ceramide crystals can be suppressed as compared with conventional ceramide-containing compositions. Therefore, it is excellent in sensory characteristics such as moist and sticky when used in cosmetics.

As the ceramide of the component (a) that can be used in the present invention, various substances known as ceramides such as natural ceramides, synthetic ceramides, and analogs thereof obtained by synthesis or the like (synthetic pseudoceramide) can be used. .
For example, as ceramide, ceramide 1, ceramide 2, ceramide 3, ceramide 4, ceramide 5, ceramide 6, ceramide 7, animal brain extract, phytoceramide, glycosphingolipid (plant ceramide), ceraminol, ceramide complex, etc. Plant extracts; natural ceramides such as ceramide-sphingosine complex and ceramide and mixtures thereof; synthetic optically active ceramides such as optically active ceramide 2 (ceramide TIC-001) and optically active ceramide 3; O-acylceramides, stearoyl dihydrosphingosine, Stearoyl phytosphingosine, hydroxyethyl palmityloxyhydroxylpropyl palmitamide (ceramide SL), trihydroxypalmitamide hydroxypropyl myristyl ether (ceramide H03), Examples thereof include N- (hexadecyloxyhydroxypropyl) -N-hydroxyethyldecanamide, N- (hexadecyloxyhydroxypropyl) -N-hydroxyethylhexadecanamide, and the like.
The ceramides can be used alone or in admixture of two or more. Among the ceramides, saccharide ceramide is particularly preferable, and saccharide ceramide is contained in a large amount in ceramide derived from animals.

Component (b) that can be used in the present invention is an esterification product of glycerin, a fatty acid having 8 to 30 carbon atoms and an aliphatic saturated dibasic acid.
The fatty acid having 8 to 30 carbon atoms is preferably a fatty acid having 14 to 26 carbon atoms. As the fatty acid, one kind or two or more kinds of fatty acids may be used from linear, branched, saturated and unsaturated. Examples of fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, 10-hydroxystearic acid, 10-ketostearic acid, 12-hydroxystearic acid, arachidic acid, behenic acid, and montanic acid. .
A preferred fatty acid in the present invention includes behenic acid that facilitates high-pressure emulsification of ceramide.

The aliphatic saturated dibasic acid preferably has 9 to 20 carbon atoms, and a dibasic acid such as nonanedioic acid, decanedioic acid, dodecanedioic acid, octadecanedioic acid, and eicosanedioic acid is used alone or in any mixture. it can. Of these, eicosane diacid is preferred.
In order to obtain the component (b), the ratio of the fatty acid having 8 to 30 carbon atoms and the aliphatic saturated dibasic acid is suitably 1 (mol): 0.1 to 0.5 (mol). Moreover, 1-5 mol is suitable with respect to 1 mol of the former about the ratio of the transesterification reaction of glycerol and the said fatty-acid total amount. The catalyst for the esterification reaction may be either an enzyme or a chemical catalyst.
Component (b) is prepared by subjecting glycerin and the fatty acid and the aliphatic saturated dibasic acid to an oligoesterification reaction at the same time or by esterifying glycerin and a fatty acid first, and further adding the aliphatic saturated dibasic acid and the oligoester. An esterification reaction or a transesterification reaction is performed, or a method in which glycerin and an aliphatic saturated dibasic acid are first oligoesterified and then esterified with a fatty acid, for example, by the method described in Japanese Patent No. 2700377 be able to. Moreover, the component (b) can use suitably the esterification product marketed as a brand name nom coat HK-G from Nisshin Eulio Group.

Component (c) that can be used in the present invention is an ester of polyglycerol and a fatty acid.
Polyglycerin is a glycerin polymer having a structure in which hydroxyl groups bonded to primary carbon atoms of glycerin are linked by an ether bond by dehydration condensation. The degree of polymerization of glycerin varies depending on the type of fatty acid and the type of ester, but the average degree of polymerization is 3-20. Triglycerin, tetraglycerin, hexaglycerin, decaglycerin and the like can be exemplified, and these can be used alone or as a mixture. A preferred polymerized glycerin for the present invention is decaglycerin.

The fatty acid which comprises a component (c) can use the C8-C30 fatty acid illustrated by the component (b), and a suitable fatty acid is behenic acid which is easy to carry out high-pressure emulsification of ceramide.
The molar ratio of polyglycerin to fatty acid in component (c) is preferably about 0.8 to 3.0 on average with respect to polyglycerin 1.
Preferable examples of the component (c) include polyglyceryl monostearate and polyglyceryl distearate.

  The oil constituting component (d) is an oily substance, and is not particularly limited as long as it is an oil that can contribute to the emulsifying action of ceramide. Examples of the oil that can be used include hydrocarbons, esters, oils and fats, waxes, higher fatty acids, higher alcohols, silicone substances, sterols, resins, and the like. More specifically, liquid paraffin, isoparaffin, petrolatum, squalane, isopropyl myristate, octyldodecyl myristate, cetyl isooctylate (cetyl 2-ethylhexanoate), glyceryl triisooctylate (glyceryl tri-2-ethylhexanoate) ), Glyceryl tricaprylate, neopentyl glycol diisooctylate (di-2-ethylhexanoic acid neopentyl glycol ester), diisostearyl malate, isononyl isononanoate (3,5,5-trimethylhexanoic acid 3,5,5) -Tripentahexyl alcohol ester), stearic acid hydrogenated castor oil, cholesteryl 12-hydroxystearate, mono- or hexaisostearic acid dipentaerythritol using isostearic acid manufactured by Emery Ester, o, m or isooctyl methoxycinnamate, eucalyptus oil, soybean oil, cottonseed oil, sesame oil, rice germ oil, rice bran oil, safflower oil, sunflower oil, palm oil, olive oil, jojoba oil, macadamian nut Oil, avocado oil, castor oil, evening primrose oil, turtle oil, mink oil, orange luffy oil, lanolin, myristic acid, palmitic acid, stearic acid, oleic acid, 12-hydroxystearic acid, behenic acid, stearic alcohol, oleyl alcohol, Cetanol, lanolin alcohol, paraffin wax, microcrystalline wax, ceresin wax, beeswax, carnauba wax, candelilla wax, shellac wax, hardened soybean oil, rapeseed hardened oil, glyceryl tristearate, rosin, cholesterol, phyll Sterols, dimethyl polysiloxane, and the like essential oil components methylphenyl polysiloxane, and animal and plant origin. These can be used alone or in combination.

The polyhydric alcohol of component (e) is not particularly limited, and examples thereof include glycerin, 1,3 butylene glycol, propylene glycol, isoprene glycol, sorbitol, erythritol, maltose, maltitol, xylitol, xylose, trehalose, glucose, Examples thereof include mannitol, pentaerythritol, pentylene glycol, hexylene glycol, diglycerin, and polyglycerin having an average degree of polymerization of 3 or more. These polyhydric alcohols can be used alone or in admixture of two or more. Among these, trihydric alcohols are preferable, and glycerin is particularly preferable.
Examples of the component (f) water include purified water, clean water, hot spring water, and deep water.

  Furthermore, the use of a thickener is effective to contribute to stability and to change the sensation. Although there is no particular limitation as a thickener, carboxyvinyl polymer, alkyl-modified carboxyvinyl polymer, cellulose, acrylic acid amide and derivatives thereof, keratin and collagen or derivatives thereof, calcium alginate, pullulan, agar, gelatin, tamarind seed polysaccharide, Examples include xanthan gum, carrageenan, high methoxyl pectin, low methoxyl pectin, guar gum, gum arabic, crystalline cellulose, arabinogalactan, caraya gum, tragacanth gum, alginic acid, albumin, casein, curdlan, gellan gum, dextran and the like.

  In addition, other components that are usually used in preparations such as cosmetics, quasi-drugs, and external medicines, that is, alcohols, surfactants, powders, additives, are included within the scope of the present invention. Sticky agent, UV protection agent, antibacterial agent, flavoring agent, pH adjuster, refreshing agent, plant / animal / microbe-derived extract, blood circulation promoter, astringent, anti-seborrheic agent, whitening agent, anti-inflammatory agent, anti-wrinkle 1 type (s) or 2 or more types, such as an agent, an active oxygen scavenger, an antioxidant, a cell activator, a moisturizer, or a chelating agent, can be added.

  The blending ratio of the ceramide-containing emulsion composition varies depending on, for example, the amount of the esterification product with glycerin and the amount of polyglycerin fatty acid ester, but the ceramide of component (a) is 0.001-1 based on the whole composition. 0.0 wt%, preferably 0.005 to 1.0 wt%, more preferably 0.01 to 0.5 wt%, and the esterification product of component (b) is 0.1 to 2 wt%. The total amount of the ceramide of component (a) and the oil of component (d) is 0.01 to 30% by weight. The weight ratio of oil to ceramide is 0.001 to 0.1 for ceramide with respect to oil 1, and 0.05 to 0. 5.

The ceramide-containing emulsion composition can be obtained by blending the above raw materials and emulsifying under high pressure.
The high pressure emulsification is not particularly limited as long as it is an emulsifier capable of high pressure processing. Examples of the existing high-pressure emulsifier include a microfluidizer (manufactured by Microfluidic Corporation), a nanomizer (manufactured by Nanomizer Co., Ltd.), an optimizer (manufactured by Sugino Machine Co., Ltd.), and a HOMOGENAIZER (manufactured by Manton-Gaulin). ) And the like.
The treatment pressure varies depending on the type and amount of components or the number of treatments, but is preferably 500 to 2000 kg / cm ² , preferably 800 to 2000 kg / cm ² .
High-pressure emulsification does not need to be carried out for the entire formulation containing all raw materials, high-pressure emulsification is performed on the blended part of some necessary raw materials, and the remainder can be mixed with ordinary stirring, depending on the blended raw materials, etc. You can choose. This is selected when high-pressure emulsification treatment should not be performed on some sticking agents, etc. in addition to the merit of efficient emulsification.

  The ceramide-containing emulsion composition of the present invention can be used as a cosmetic composition, a skin external preparation composition, a bath preparation composition, and the like because a stable emulsion composition is obtained without precipitation of ceramide crystals.

Example 1 to Example 4, Comparative Example 1 to Comparative Example 4
Using the formulation shown in Table 1, a ceramide-containing emulsion composition was prepared by the following method. In addition, a numerical value is a weight ratio. Formulation A was warmed to 90 ° C. and added to Formulation B with stirring. In particular, it is useful in the present invention that glycerin is contained at this stage. This was processed once using a microfluidizer (M-110EH manufactured by Mizuho Kogyo Co., Ltd.) at a pressure of 1265.5 kg / cm ² (18000 psi) and an introduction temperature of 70 ° C. Thereafter, Formulation C was added with normal stirring (atmospheric pressure, rotation speed 2000 rpm, stirring time 10 minutes, and stirring temperature 30 ° C.).
The raw materials used in the formulation shown in Table 1 are as follows.
Formulation A
(A-1): Ceramide 2 (Ceramide TIC-001 (manufactured by Nikko Chemicals Co., Ltd.))
(A-2): Animal extraction ceramide (Bioceramide CH (manufactured by Yamakawa Trading Co., Ltd.))
(A-3): Ceramide 6 (Ceramide VI (Nikko Chemicals Co., Ltd.))
(A-4): Glycerin fatty acid ester eicosane diacidification product (Nomcoat HK-G (Nisshin Oilio Group Co., Ltd.))
(A-5): Squalane (A-6): Glyceryl tri-2-ethylhexanoate (A-7): Stearic acid hydrogenated castor oil (Castlite MS (manufactured by National Mimatsu Co., Ltd.))
(A-8): dextrin palmitate (manufactured by Chiba Flour Mills, trade name Leopard KS)
Formulation B
(B-1): Polyglycerin A monostearate (Decagrin 1-SV (manufactured by Nikko Chemicals))
(B-2): Polyglycerin B monostearate (Saracos PGMSV (manufactured by Nisshin Oilio Group Co., Ltd.))
(B-3): Polyglyceryl distearate (Decagrin 2-SV (manufactured by Nikko Chemicals Co., Ltd.))
(B-4): Glycerin (B-5): 1,3 Butylene glycol (B-6): Purified water formulation C
(C-1): Carboxyvinyl polymer 1% aqueous solution (pH 7.0 neutralized) (Hibiswako 104 (manufactured by Goodrich))
(C-2): Xanthan gum (San Ace C (manufactured by Saneigen FFI Co., Ltd.))
(C-3): Purified water

The viscosity of the ceramide-containing emulsion composition obtained in each example and comparative example was measured at 25 ° C. using a BH viscometer. Examples 1 and 4 were measured at 10 rpm using a No. 3 rotor, and Examples 2 and 3 were measured at 20 rpm using a No. 2 rotor. The results are shown in Table 1.
In addition, each example and each comparative example were hermetically stored in a test container and left in a constant temperature bath at 40 ° C. for 1 week, and then the state of the emulsified composition was visually confirmed. All the examples were unchanged. However, crystals were precipitated in all of the comparative examples. In addition, when neither glycerin fatty acid ester eicosane diacidification product nor dextrin palmitate was blended, precipitation was observed from the beginning because emulsification was impossible.

Using the ceramide-containing emulsion composition obtained in each example and each comparative example, a cream for sensory testing (formulation is wt%) was prepared by the following method.
A: Squalane 10.0
Capryl caproic acid triglyceride 10.0
Gaylow 5.0
Beeswax 5.0
Silicone 0.5
B: Purified water 41.3
Ceramide-containing emulsion composition 0.5
6% colloidal hydrous silicate aqueous solution 15.0
Glycerin 10.0
Polyethylene glycol (average molecular weight 4000) 2.0
Methyl paraoxybenzoate 0.2
Hyaluronic acid Na 0.5
A and B are weighed and dissolved by heating. A and B were mixed with stirring to obtain a cream for sensory test.
The face of each of five women was divided into left and right, one day each of which was used as a cream of each example, and the other was used as a cream of each comparative example. Note that Comparative Example 1 was used for Example 1, Comparative Example 2 for Example 2, Comparative Example 3 for Example 3, and Comparative Example 4 for Example 4.
In the evaluation, the case where there was a moist feeling on the skin and there was no sticky feeling and the example was much better than the comparative example was scored as +++ points, and the case where there was no difference was scored as + points. The results are shown in Table 1.
Each example gave good results including a very moist feeling.

表１において、各実施例は結晶の析出が見られず、また官能検査においても優れていた。各比較例は、マイクロフルイダイザーで処理した後にすでに乳化が正常に行われておらず、セラミドが析出している状態であった。また、各比較例の粘度そのものは各実施例と比べて略同じであった。また、実施例１〜４と同じ配合物をマイクロフルイダイザーで処理の替わりにホモジナイザー（特殊機化工業株式会社製Ｔ．Ｋ．オートホモミクサーＭＡＲＫ ＩＩ ４０型）で５０００ｒｐｍ、１０分間処理したものは結晶の析出を見た。

In Table 1, no precipitation of crystals was observed in each example, and the sensory test was also excellent. In each comparative example, emulsification was not normally performed after treatment with the microfluidizer, and ceramide was precipitated. Moreover, the viscosity itself of each comparative example was substantially the same as that of each example. Moreover, what processed the same compound as Example 1-4 with a homogenizer (TK auto homomixer MARK II 40 type | mold by the special machine chemical industry company) for 10 minutes instead of processing with a microfluidizer for 10 minutes. A crystal precipitation was observed.

  The ceramide-containing emulsion composition of the present invention has no precipitation of ceramide crystals as compared to conventional ceramide-containing compositions and is very effective in terms of functionality, so a cosmetic composition, a skin external preparation composition, Application to bathing agent compositions is expected.

Claims (4)

A ceramide-containing emulsion composition characterized by emulsifying a mixture containing the following components (a), (b), (c), (d) and (e) at a pressure of 500 to 2000 kg / cm ^2. object.
(A) Ceramide (b) Esterification product of glycerin, fatty acid having 8 to 30 carbon atoms and aliphatic saturated dibasic acid (c) Polyglycerin fatty acid ester (d) Oil (e) Polyhydric alcohol   The ceramide-containing emulsion composition according to claim 1, wherein the polyhydric alcohol is glycerin. A mixture containing the following component (a), component (b), and component (d) was mixed with a formulation containing component (c) and component (e) to obtain a mixture, and then the mixture For producing a ceramide-containing emulsified composition by emulsifying at a pressure of 500 to 2000 kg / cm ² .
(A) Ceramide (b) Esterification product of glycerin, fatty acid having 8 to 30 carbon atoms and aliphatic saturated dibasic acid (c) Polyglycerin fatty acid ester (d) Oil (e) Polyhydric alcohol A blend containing the following component (a), component (b), and component (d) is mixed with a blend containing a part of component (c), component (e) and component (f) After obtaining the mixture, the mixture is emulsified at a pressure of 500 to 2000 kg / cm ² , and the resulting emulsified product is mixed with the component (f) and stirred to produce a ceramide-containing emulsion composition. Method.
(A) Ceramide (b) Esterification product of glycerin, C8-30 fatty acid and aliphatic saturated dibasic acid (c) Polyglycerin fatty acid ester (d) Oil (e) Polyhydric alcohol (f ) water