JP6562921B2 - Human sebum mimetic derived from plant sources and method for producing the same - Google Patents

Description

CROSS REFERENCE TO RELATED APPLICATIONS This application claims benefit based on US Provisional Patent Application No. 61 / 697,240 filed on Sep. 5, 2012 and is filed on Oct. 26, 2009. US patent application Ser. No. 12 / 911,150, filed Oct. 25, 2010, which claims the benefit of US Provisional Patent Application No. 61 / 363,564, filed Jul. 12, 2010, and US Provisional Patent Application No. 61 / 363,564, filed Jul. 12, 2010. No. 13 / 689,501 filed Nov. 29, 2012 (current U.S. Pat. No. 8,765,106), which is a continuation of the present U.S. Pat. This application is a divisional application of US patent application Ser. No. 12 / 911,150 filed Oct. 25, 2010 (current US Pat. No. 8,343,468), 2012. Year 1 This is a continuation of US Patent Application No. 13 / 685,206 filed Jan. 26 (current U.S. Patent No. 8,765,105) and is filed in the United States filed Oct. 25, 2010. US patent application Ser. No. 13 / 776,199, filed Feb. 25, 2013, which is a reissue application of patent application No. 12 / 911,150 (current US Pat. No. 8,343,468) U.S. Reissue Patent No. 44,718), which is incorporated by reference in its entirety. However, as long as the present application is inconsistent with any reference application, the present disclosure should prevail.

TECHNICAL FIELD The present invention relates generally to personal care compositions and methods for producing the same, and more particularly to human sebum mimetics derived from plant sources and methods for producing the same.

BACKGROUND OF THE INVENTION Human sebum is secreted by sebaceous glands that are found throughout substantially the entire skin surface (except palms and soles) but are found primarily in the scalp, face, chest, and back. Sebum is involved in developing the epidermal structure and maintaining the epidermal permeability barrier, transporting antioxidants to the skin surface, protecting the skin from microbial colonization, generating body odor, and providing UV protection.

  When secreted, human sebum is a complex mixture of triglycerides, wax esters, cholesterol, cholesterol esters, and squalene. During sebum secretion it consists mainly of triglycerides and wax esters, which are broken down by microorganisms into diglycerides, monoglycerides and constituent free fatty acids. Fatty acid chain lengths in human sebum vary considerably, but stearic acid (18 carbon atoms and no double bonds (hereinafter expressed as 18: 0)), oleic acid (9th carbon) Of 18: 1 (hereinafter represented by 18: 1Δ9), linoleic acid (18: 2Δ9Δ12), palmitic acid (16: 0), and sapienoic acid (16: 1Δ6) containing one double bond As is the case, the carbon numbers are mainly 16 and 18.

  Sebum loss over time can be attributed to various environmental and genetic factors such as bathing, weather conditions, chemical products, malnutrition. For example, African-American scalp has a natural sebum deficiency. Loss of sebum can cause itching, head rash, itching and diaper rash on the skin. In addition, hair may become brittle and dry if there is not enough sebum to moisturize it. There are various products that have tried to restore flexibility due to lack of sebum, but many of these products contain synthetic or animal-derived ingredients and do not mimic the structure and composition of human sebum . In this context, these products are not as easily absorbed by the skin as human sebum. In addition, these products are often manufactured from unstable ingredients that exhibit short shelf life.

  Accordingly, it is desirable to provide a stable human sebum mimetic produced from a plant source. It is also desirable to provide a method for producing human sebum mimetics. Furthermore, other desirable features and characteristics of the present invention will become apparent in view of the subsequent detailed description of the invention and the appended claims, taken in conjunction with the background of the invention.

SUMMARY OF THE INVENTION Human sebum mimetics and methods for producing human sebum mimetics are provided. In one exemplary embodiment, the human sebum mimetic comprises a wax ester obtained by transesterification of purified vegetable triglyceride oil containing palmitoleic acid with jojoba oil (optionally purified), phytosterol, and phytosqualene. , May be included.

  In another exemplary embodiment, a method for producing human sebum mimetics comprises the steps of mixing refined macadamia oil and refined jojoba oil, transesterifying macadamia oil and jojoba oil, and phytosterols before or after transesterification. And a step of adding phytosqualene after transesterification.

  In a further exemplary embodiment, the human sebum mimetic comprises a wax ester having a C 16 fatty acid containing one double bond (the wax ester is derived from a plant source), phytosterol, and phytosqualene. May be included.

  In a further exemplary embodiment, the human sebum mimetic comprises a wax ester having a fatty acid of 16 carbon atoms including one double bond (the wax ester is derived from a plant source), phytosterol, phytosqualene, and phyto Steryl acylate.

  In a further exemplary embodiment, the human sebum mimetic is a wax ester, phytosterol, phytosqualene, and phytosteryl macadamite obtained by transesterification of a refined vegetable oil containing hexadec-9-enoic acid with refined jojoba oil. And can be included.

  In a further exemplary embodiment, the human sebum mimetic is a wax ester, phytosterol, phytosqualene, phytosteryl macadamate, and human keratin obtained by transesterification of a refined vegetable oil containing palmitoleic acid with refined jojoba oil. And the constituent lipids of the layer.

DETAILED DESCRIPTION The following detailed description is merely exemplary in nature and is not intended to limit the invention or the application and uses of the invention. Furthermore, there is no intention to be bound by any theory presented in the preceding background or the following detailed description.

Various embodiments envisioned herein relate to compositions that mimic human sebum. An approximate composition of human sebum contains the following in weight percent (wt.%) Units (excerpted from Pierre Agache, “Sebaceous Physiology,” Measuring The Skin, Springer-Verlog, 2004, pp. 271-280).
Squalene 12 wt. %
Wax ester 26 wt. %
Glycerides and free fatty acids 57.5 wt. %
Sterol (free type and ester type) 4.5 wt. %
The human sebum mimetics envisioned herein are botanical. That is, the components of mimetics are obtained physically or chemically from plant sources. In this context, mimetics consist of phytosqualene, phytosterols, vegetable oils (optionally refined) such as macadamia oil (which is a source of mimetic triglycerides), and jojoba oil (a source of mimetic wax ester fractions). Is a plant-derived analog of human sebum in that it is obtained from As used herein, the term “refined oil” means a crude oil from which undesirable compounds such as free fatty acids, carbohydrates, metals, proteins have been removed. In one embodiment, the human sebum mimetic is about 5 to about 20 wt. % Phytosqualene and about 20 to about 35 wt. % Of refined jojoba oil and about 45 to about 65 wt. % Of refined macadamia oil and about 0.5 to about 10 wt. % Phytosterol. In an exemplary preferred embodiment, the human sebum mimetic is about 11 to about 15 wt. % Phytosqualene and about 29 to about 33 wt. % Of refined jojoba oil and about 51 to about 55 wt. % Of refined macadamia oil and about 1 to about 5 wt. % Phytosterol. In an exemplary more preferred embodiment, the human sebum mimetic is obtained from the following composition substantially in weight percent units:
Phytosqualene 12.9 wt. %
Refined jojoba oil 30.8 wt. %
Refined macadamia oil 53.2 wt. %
Phytosterol 3.1 wt. %

  Human sebum has a particularly high level of hexadecenoic acid (16: 0) (also referred to as palmitic acid), sapienoic acid (16: 1Δ6), and oleic acid (C18: 1Δ9). Similarly, the human sebum mimetic envisaged herein also has macadamia oil itself of about 8.8 wt% palmitic acid and about 58 wt. % Oleic acid, so it contains a high level of palmitic acid and oleic acid. In one embodiment, the human sebum mimetic is about 1 to about 10 wt. % Palmitic acid, in a preferred embodiment from about 3 to about 7 wt. % Palmitic acid, in a more preferred embodiment about 4.8 wt. % Palmitic acid. In other embodiments, the human sebum has about 25 to about 35 wt. % Oleic acid, in a preferred embodiment from about 30 to about 34 wt. % Oleic acid, in a more preferred embodiment about 31.6 wt. % Oleic acid.

  However, sapienoic acid is unique to mammals. Hexadeca-9-enoic acid (16: 1Δ9) (also referred to as palmitoleic acid), an analog of sapienoic acid, is an alternative to sapienoic acid. Although palmitoleic acid is fairly rare in the plant kingdom, macadamia oil contains about 16-22% palmitoleic acid and has the highest palmitoleic acid content of currently available commercial oils. Accordingly, the present inventors have found that a wax ester containing palmitoleic acid is obtained by transesterification between refined macadamia oil and refined jojoba oil of human sebum mimetic. Macadamia oil is preferred, but other seed oils containing more than 10% palmitoleic acid can also produce wax esters containing palmitoleic acid by transesterification with refined jojoba oil. The genera of these species include Thunbergia, Doxantha, Alophia, Roureopsis, Telopea, and Asclepias.

  In one embodiment, the human sebum mimetic is about 5 to about 15 wt. % Of palmitoleic acid. In preferred embodiments, the human sebum mimetic is about 8 to about 12 wt.% Of the total mimetic composition. In a more preferred embodiment, the human sebum mimetic comprises about 9.7 wt.% Of the total mimetic composition. % Of palmitoleic acid. In the most preferred embodiment, the human sebum mimetic comprises the following fatty acids and fatty alcohols in weight percent units.

  In other exemplary embodiments, the human sebum mimetic can include acylate. The acylate can comprise an acylated alcohol from which the alcohol is derived from any suitable source. The acylated alcohol can be a stearyl ester. In one embodiment, the stearyl ester can be phytosteryl acylate. The phytosteryl acylate can be an ester of phytosterol and a fatty acid derived from any suitable plant source. For example, phytosteryl acylate can include phytosteryl macadamite derived from macadamia oil.

  In other exemplary embodiments, the human sebum mimetic may comprise a constituent lipid profile of sebum of any selected profile, such as an exemplary 22 year old human female. The human sebum mimetic is about 24.9 wt. % Transesterification of refined jojoba oil and refined vegetable oil containing triglycerides. However, this refined vegetable oil is about 61.9 wt. % Of palmitoleic acid. In one embodiment, the refined vegetable oil comprising palmitoleic acid can comprise refined macadamia oil. The mimetic is about 12.6 wt. % Phytosqualene, about 0.4 wt. % Phytosterol, about 0.1 wt. % Phytosteryl macadamate, and / or about 0.1 wt. % Tocopherol in an amount of about 1000 parts per million.

  In various embodiments of the present invention, the human sebum mimetic may further comprise an effective amount of any constituent lipid found in the stratum corneum of the epidermis. In one embodiment, the human sebum mimetic may comprise a derivative and / or precursor of a constituent lipid. In one embodiment, the constituent lipids are present in the human sebum mimetic in an amount effective to organize the intercellular lamellar lipid structure of the stratum corneum and at least partially promote and / or maintain skin water permeability barrier function. Yes. For example, in one embodiment, the constituent lipids can include fatty acids such as long chain saturated fatty acids having a chain length of C16 to C30 and / or unsaturated fatty acids such as linoleate. In other embodiments, the constituent lipids can include ceramides and / or sphingolipids. Ceramides can include a wide variety of structurally diverse sphingolipid base derivative families that are amide linked to various long chain fatty acids. For example, the ceramide can include any one or more ceramides found in the human stratum corneum, such as acyl ceramides. In one embodiment, the mimetic is about 27 wt. % Of ceramide may be included. The sphingolipid may comprise any one or more of a structurally diverse lipid family. For example, sphingolipids may have a C18 amino alcohol skeleton, sometimes referred to as a sphingoid base. In one embodiment, the mimetic is about 27 wt. % Of sphingolipids may be included.

  In various embodiments of the invention, the constituent lipids can include phospholipids. Phospholipids can include any lipid containing phosphoric acid as a monoester or diester. In one embodiment, the phospholipid can include any of the amphiphilic phospholipids that are part of the major component of the cell membrane. For example, in various embodiments, the phospholipid can include one or more of phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, and / or phosphatidylserine. In other embodiments, the phospholipid may comprise a phospholipid derivative such as sphingomyelin.

  In one embodiment, the phospholipid can be at least partially purified from a source. The source can include any suitable phospholipid source, such as soybean oil, rapeseed oil, and / or sunflower oil. In other embodiments, the phospholipid may be provided in an unpurified source such as lecithin.

  In various embodiments of the invention, the phospholipid is present in the human sebum mimetic in an amount effective to provide one or more derivatives for stratum corneum biosynthesis, eg, biosynthesis of ceramide I. sell. In other embodiments, the phospholipid is present in the human sebum mimetic in an amount effective to organize an extracellular mono- or oligo-lamellar layer on the skin to at least partially promote and / or maintain skin barrier function. Can exist. In other embodiments, the phospholipid may remain on the skin after washing. In yet other embodiments, the phospholipids at least partially improve skin moisture, improve skin inflammation such as atopic dermatitis and / or acne vulgaris, protect the skin from defatting, and / or The skin smoothness can be improved.

  In various embodiments of the present invention, phospholipids may constitute a transdermal delivery system for transporting active agents such as fat-soluble vitamins, vegetable oils, and / or other active ingredients to the stratum corneum of the skin. For example, in one embodiment, the delivery system can include liposomes having an inner aqueous core encapsulated within one or more phospholipid layers. In one embodiment, the delivery system may further comprise a lipophilic active agent comprising a non-phospholipid component, eg, 1% tocopherol. The delivery system can include any shape or size that facilitates fixation and / or penetration of the stratum corneum to deliver the active agent to the skin.

In various embodiments of the present invention, any human sebum mimetic may further comprise an effective amount of a minor component of the stratum corneum of the epidermis. In one embodiment, for example, the minor component can include cholesterol, such as cholesterol sulfate. In some embodiments, the cholesterol sulfate is in an amount similar to the amount of cholesterol sulfate found in the stratum corneum, eg, about 2 to about 5 wt. % Can constitute part of the human sebum mimetic. In other embodiments, the trace component can be a mineral such as calcium (Ca ²⁺ ). In some embodiments, the mimetic is about 12 wt. % Trace amounts of components may be included.

  In other exemplary embodiments, the human sebum mimetic contemplated herein includes additional functional additives, ie, ingredients that are added to perform a specific function. For example, the human sebum mimetic can include tocopherol. In one embodiment, the human sebum mimetic comprises about 100 to about 2000 parts per million (ppm), preferably about 1430 ppm of 70% tocopherol. Human sebum mimetics can also include flavoring agents, dyes, pigments, preservatives, antioxidants, humectants, and the like. As a further example, the human sebum mimetic can include an emollient or thickener, such as FLORAESTERS 20 (FE-20) available from International Flora Technologies, Ltd. (Chandler, Arizona). FLORAESTERS 20 can be used to increase the viscosity and / or bulk melting point / drop point of mimetics to more closely reproduce the wax ester profile of human sebum and the like.

  As an alternative or in addition, human sebum mimetics are a hair care lotion, shampoo, hair conditioner, hair gel, hair oil, hair color, hair relaxer, hand lotion, facial lotion, eye cream, facial soap, body lotion and body cream, body It can be used as an ingredient in a wide range of personal care products such as scrubs, shaving gels, hair removers, sanitary wipes and the like. Since human sebum mimetics are very similar in composition to human sebum, they promote the natural healing and recovery system of human skin, accelerate cell turnover and local blood circulation, May reduce wrinkles under the eyes and the occurrence of senile plaques. Human sebum mimetics can also reduce scalp irritation and improve skin hydration through natural healing. Human sebum mimetics can also be used in addition to being applied to humans, and can also be used for animals and to keep fruits and vegetables fresh.

  The human sebum mimetics envisioned herein are particularly suitable as replacements for lost human sebum because of their stability. Oil stability is measured at 110 ° C. according to the American Oil Chemists' Society official method Cd 12b-92. In one embodiment, the human sebum mimetic contemplated herein has an oil stability index of greater than about 50 hours at 110 ° C. In other embodiments, the human sebum mimetic contemplated herein has an oil stability index of greater than about 40 hours at 110 ° C. In this context, mimetics are substantially oxidation resistant and have the desired shelf life as and in personal care products.

  According to an exemplary embodiment, the method for producing human sebum mimetic has one double bond by mixing refined macadamia oil and refined jojoba oil and transesterification of refined macadamia oil and refined jojoba oil. It includes a step of producing a wax ester containing a fatty acid having 16 carbon atoms, a step of adding phytosterol, and a step of adding phytosqualene. Phytosterol can be added to refined macadamia oil and refined jojoba oil before and / or after transesterification. The resulting human sebum mimetic can then be bleached and / or deodorized.

  In one exemplary embodiment, a mixture of 53.2 grams (g) refined macadamia oil, 30.8 g refined jojoba oil, and 2.1 g phytosterol is mixed and heated to 90 ° C. with stirring under vacuum. To do. After about 0.5 hours, 0.84 g of sodium methoxide is added to the mixture, the temperature is raised to 130 ° C. and maintained at that temperature for about 2 to about 2.5 hours. The mixture is then cooled to 90 ° C. and 0.84 g of citric acid is added with stirring for 0.5 hour. The mixture is then filtered. 1 g phytosterol and 12.9 g phytosqualene are added to the filtrate and mixed until uniform to obtain a mimetic. 1 wt. % Bleaching earth (Clarion 470 bleaching clay available from American Colloid Company (Arlington Heights, Ill.)) May be added to the mimetic, which is then heated to 95 ° C. and stirred under vacuum Maintain for 15-30 minutes. Filter the mixture. In order to remove odors and other volatile substances, the mimetic may be heated to 200-220 ° C. under high vacuum while injecting water vapor. Maintain this temperature for about 2 hours, then cool under reduced pressure. In a preferred embodiment, 1430 ppm of tocopherol (70%) is added and mixed in the mimetic. Any additional additives may be added at this point.

  The following are exemplary embodiments of personal care products comprising human sebum mimetics produced as described above, where each component is wt. / Wt. It is shown in%. The examples are provided for illustrative purposes only and are not intended to limit the various embodiments of human sebum mimetics in any way.

  Example 1 is a hair conditioning lotion that provides multiple functions including a moisturizing function, a polishing function, a holding function, and an anti-breaking function.

Example 1

  The hair conditioning lotion of Example 1 is made by heating the water to 45 ° C. with stirring and adding Polyquaternium-37 with moderate propeller stirring. Mix the solution until a clear gel is formed. Add the remaining ingredients of Phase A to the gel in the order listed. Phase B ingredients are added and integrated at 45 ° C. Next, the mixture of Phase B ingredients is added to Phase A ingredients with rapid propeller agitation. Heat Phase A and B ingredients to 60 ° C. and add Phase C ingredients with moderate propeller agitation. Mix all ingredients of Phase D at 60 ° C. and add to Phase ABC mixture with moderate propeller agitation. The resulting formulation is quenched on an ice water bath. Phase E fragrance is then added.

  Example 2 is another hair conditioning lotion that provides multiple functions including a moisturizing function, a polishing function, a holding function, and an anti-breaking function.

Example 2

  The hair conditioning lotion of Example 2 is made using the same method as described above for Example 1.

  Accordingly, human sebum mimetics and methods for their production are provided. Human sebum mimetics are formed from phytosqualene, phytosterols, refined jojoba oil, and refined vegetable oils such as macadamia oil, including palmitoleic acid. Human sebum has a particularly high level of its fatty acids, palmitic acid (16: 0), sapienoic acid (16: 1Δ6), and oleic acid (C18: 1Δ9). Similarly, human sebum mimetics envisioned herein also contain high levels of palmitic acid and oleic acid. In one embodiment, the human sebum mimetic is about 1 to about 10 wt. % Palmitic acid and about 25 to about 35 wt. % Oleic acid. However, sapienoic acid is unique to mammals and is rarely found in nature. We have found that transesterification of refined macadamia oil with refined jojoba oil of human sebum mimetic yields wax esters containing palmitoleic acid, which is an alternative to sapienoic acid. In one embodiment, the human sebum mimetic is about 5 to about 15 wt. % Of palmitoleic acid.

  While at least one exemplary embodiment has been presented in the foregoing detailed description of the invention, it should be appreciated that a vast number of variations exist. It should also be appreciated that the exemplary embodiment or exemplary embodiments are only examples, and are not intended to limit the scope, applicability, or configuration of the invention in any way. More precisely, the above detailed description will provide a person skilled in the art with a roadmap that is convenient for carrying out exemplary embodiments of the present invention. It should be understood that various changes can be made in the function and arrangement of elements described in an exemplary embodiment without departing from the scope of the invention as set forth in the appended claims.

Claims (23)

With jojoba oil
A wax ester obtained by transesterification with an oil containing a triglyceride having an unsaturated fatty acid skeleton ,
Phytosterols,
With phytosqualene,
Phytosteryl macadamite,
Ceramide and / or sphingolipid as a constituent lipid of human stratum corneum,
Only including,
The constituent lipid includes a phospholipid, and the phospholipid includes one or more selected from the group consisting of phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and sphingomyelin.
Human sebum mimetic composition.   The human sebum mimetic composition of claim 1, wherein the oil containing triglycerides comprises hexadec-9-enoic acid.   The oil containing the triglyceride is 10 wt. 3. The human sebum mimetic composition of claim 2, comprising greater than% hexadeca-9-enoic acid.   The human sebum mimetic composition according to claim 1, wherein the oil containing triglyceride is refined macadamia oil. 1-10 wt. The human sebum mimetic composition of claim 1, further comprising% palmitic acid. The palmitic acid is 3 to 7 wt. The human sebum mimetic composition according to claim 5, wherein the composition is%. 25-35 wt. The human sebum mimetic composition of claim 1, further comprising% oleic acid. The oleic acid is 30 to 34 wt. The human sebum mimetic composition according to claim 7, wherein the composition is%. Hexadeca-9-enoic acid is 5 to 15 wt. The human sebum mimetic composition according to claim 2, wherein the composition is%. Hexadeca-9-enoic acid is 8-12 wt. The human sebum mimetic composition according to claim 2, wherein the composition is%. The human sebum mimetic composition of claim 1, having an oil stability index of greater than 40 hours at 110 ° C.   The human sebum mimetic composition according to claim 1, wherein the constituent lipids include sphingolipids. The sphingolipid is 27 wt. The human sebum mimetic composition according to claim 12, occupying up to%.   The human sebum mimetic composition according to claim 1, wherein the constituent lipid comprises ceramide. The ceramide is 27 wt. The human sebum mimetic composition according to claim 14, comprising up to%. The human sebum mimetic composition according to claim 1, further comprising cholesterol as a minor component of the human stratum corneum of the epidermis. The human sebum mimetic composition of claim 16 , wherein the cholesterol comprises cholesterol sulfate. The human sebum mimetic composition according to claim 16 , wherein the trace component contains a mineral. The human sebum mimetic composition of claim 18 , wherein the mineral comprises calcium.   The human sebum mimetic composition according to claim 1, further comprising a functional additive. 21. The human sebum mimetic of claim 20 , wherein the functional additive is at least one of tocopherols, fragrances, dyes, pigments, preservatives, antioxidants, humectants, emollients, and thickeners. Composition.   The human sebum mimetic composition according to claim 1, wherein the human sebum mimetic composition is a component of a personal care product suitable for the care of human or animal skin or hair. 23. The human sebum mimetic composition according to claim 22 , wherein the personal care product is a hair conditioning lotion.