Method for producing oily composition

Abstract

Provided is a method for producing an oily composition having reduced odor and pigment. The method for producing an oily composition according to the present disclosure comprises: a contact step for inducing contact between a plant-derived oil-soluble extract and a porous body; and a solid-liquid separation step for recovering an oily composition by solid-liquid separation of the oil-soluble extract from the porous body.

Description

Method for producing oily composition

[0001] The present disclosure relates to a method for producing an oily composition.

[0002] The odor of raw materials used in cosmetics and the like can be unpleasant for users, so fragrances and the like are used to eliminate the odor (Patent Document 1). In recent years, there has been an increasing demand for fragrance-free cosmetics that do not contain added fragrances, due to the user's constitution and from the perspective of natural preferences. For this reason, there is a demand for raw materials that are odorless or have a reduced odor.

[0003] Furthermore, since the color of the raw material affects the color of cosmetics and the like, it is preferable that the raw material be colorless or nearly colorless.

[0004] Patent No. 7492638

[0005] Therefore, an object of the present disclosure is to provide, for example, a method for producing an oily composition with reduced odor and pigment.

[0006] In order to achieve the above-mentioned object, the method for producing an oily composition of the present disclosure includes: a contacting step of bringing an oil-soluble extract derived from a plant into contact with a porous body; and a solid-liquid separation step of performing solid-liquid separation between the oil-soluble extract and the porous body to recover an oily composition.

[0007] According to the present disclosure, for example, it is possible to provide a method for producing an oily composition with reduced odor and pigment.

[0008] The present disclosure will be specifically described below using examples. Unless otherwise specified, each disclosure may incorporate the explanations of other disclosures.

[0009] <Definitions> In this specification, "oil-soluble extract" and "oil-based composition" refer to a composition containing an oily component as a main component. The term "oil-soluble" or "oil-soluble" can also be used to refer to, for example, fat-soluble or lipophilic. Examples of the oily component include components with low molecular polarity and low solubility (affinity) in aqueous solvents, and components that are insoluble in water.

[0010] In this specification, "bakuchiol" refers to a compound represented by 4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol. It is known that bakuchiol is extracted from the seeds of Psoralea corylifolia, an annual plant of the legume family. The bakuchiol can also be a compound represented by the following formula (1): The bakuchiol may be, for example, a phenoxide ion. The bakuchiol may also be, for example, esterified.

[0011] The present disclosure will be described below using examples, but the present disclosure is not limited to the following examples and can be implemented with any modifications. Furthermore, the descriptions in this disclosure and each embodiment can be mutually incorporated unless otherwise specified. In this specification, when the expression "~" is used, it is used to mean including the numerical or physical values ​​before and after it. In addition, in this specification, the expression "A and / or B" includes "A only," "B only," and "both A and B."

[0012] <Method for producing oily composition> In one aspect, the present disclosure provides a method for producing an oily composition (hereinafter also referred to as "production method"). The production method of the present disclosure includes a contacting step of bringing a plant-derived oil-soluble extract into contact with a porous body, and a solid-liquid separation step of performing solid-liquid separation between the oil-soluble extract and the porous body to recover an oily composition. According to the production method of the present disclosure, an oily composition with reduced odor and pigment can be produced.

[0013] As a result of extensive research, the present inventors have discovered that by using a porous body, an oil-based composition with reduced odor and pigments can be produced from a plant-derived oil-soluble extract, leading to the establishment of the present disclosure. It is believed that the reduction in odor and pigments is due to the adsorption of odor-causing components and pigments by the porous body. However, this assumption does not limit the present disclosure in any way. Therefore, according to the present disclosure, it is possible to produce an oil-based composition with reduced odor and pigments.

[0014] Examples of the plant include Psoralea corylifolia, Otholobium pubescens, and olive (Olea europaea).

[0015] The plant-derived oil-soluble extract is, for example, an extract containing oil-soluble components derived from the plant, and can be produced by extracting the plant with an organic solvent. In this case, the plant oil-soluble extract can also be referred to as an "organic solvent extract of a plant." The plant-derived oil-soluble extract may be, for example, an extract extracted with the organic solvent, a crude product obtained by crudely purifying the desired oily components from the extracted extract, or a purified product obtained by purifying the desired oily components from the extracted extract, or a product obtained by removing the organic solvent used for the extraction from any of these.

[0016] Examples of the organic solvent used in the extraction include lower alcohols or hydrous lower alcohols such as methanol, ethanol, propyl alcohol, isopropyl alcohol, butanol, and isobutanol; polyhydric alcohols or hydrous polyhydric alcohols such as propylene glycol, 1,3-butylene glycol, 1,2-butylene glycol, 1,4-butylene glycol, 1,5-pentanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, 1,3,5-pentanetriol, glycerin, and polyethylene glycol (e.g., molecular weight of 100 to 100,000); acetone, ethyl acetate, diethyl ether, dimethyl ether, ethyl methyl ether, dioxane, hexane, acetonitrile, xylene, benzene, chloroform, carbon tetrachloride, phenol, and toluene.

[0017] The oil-soluble extract may contain, for example, bakuchiol.In this case, the oil-soluble extract is, for example, an oil-soluble extract containing bakuchiol as the desired oil component.The oil-soluble extract containing bakuchiol may be prepared by oneself or may be a commercially available product.When using a commercially available product, for example, bakuchiol manufactured by Varion Co., Ltd., bakuchiol manufactured by BIB Corporation, etc. may be mentioned.

[0018] When the oil-soluble extract contains bakuchiol, the oil-soluble extract may be produced by subjecting a plant containing bakuchiol to the organic solvent extraction used for the extraction described above. Examples of plants containing bakuchiol include Psoralea corylifolia and Otholobium pubescens. One or more types of plants may be used. The plant material used for the extraction may be an entire plant or a plant part. Examples of plant parts include roots, rhizomes, leaves, stems, whole flowers, or a mixture thereof. The material may be the collected plant itself or a processed product obtained by drying and / or pulverizing.

[0019] In the manufacturing method of the present disclosure, as described above, in the contacting step, the plant-derived oil-soluble extract is contacted with a porous body. As a result, odor-causing components and color components contained in the oil-soluble extract are supported (held) or adsorbed on the porous body. The contacting can be carried out, for example, by a known solid-liquid contacting method, specifically, by mixing or blending (hereinafter collectively referred to as "blending") the oil-soluble extract and the porous body.

[0020] In the contacting step, the plant-derived oil-soluble extract may be contacted with an organic solvent and the porous body to promote adsorption of odor-causing components and color components contained in the oil-soluble extract to the porous body. That is, in the contacting step, for example, the oil-soluble extract may be contacted with the porous body in a state diluted with the organic solvent. The contacting may be carried out, for example, by a known solid-liquid contacting method, specifically by mixing the oil-soluble extract, the organic solvent, and the porous body. The contacting of the oil-soluble extract with the organic solvent and the porous body may be carried out, for example, by contacting the oil-soluble extract, the organic solvent, and the porous body all at once, or sequentially. In the latter case, the oil-soluble extract may be contacted with the organic solvent and then the porous body is added; the oil-soluble composition may be contacted with the porous body and then the organic solvent is added; or the oil-soluble composition may be contacted with the organic solvent and then the porous body is added. When the oil-soluble extract is first contacted with the organic solvent, the contact can also be referred to as, for example, dilution.

[0021] Examples of the organic solvent used in the contact include methanol, ethanol, butyrol (eg, n-butyrol), propanol, phenoxyethanol, ethyl acetate, butyl acetate, hexane, and cyclohexane.

[0022] Examples of the porous body include inorganic porous bodies and organic porous bodies. Examples of the inorganic porous body include porous bodies composed of silica (silicon dioxide), magnesia (magnesium oxide), alumina (aluminum oxide), zeolite, or a mixture thereof; porous silicon; and the like. The mixture may be, for example, a composite of each component, a specific example being silica magnesia. Examples of the silica magnesia include the Mizuka Fine (trademark) series (e.g., Mizuka Fine SM200) from Mizusawa Industrial Chemicals Co., Ltd. Examples of the organic porous body include activated carbon, organic polymer materials, porous starch, dextrin, cellulose, and the like. Examples of the activated carbon include the Shirasagi series (e.g., Shirasagi A) from Osaka Gas Chemicals Co., Ltd. Examples of the organic polymer material include crosslinked polymers such as aromatic vinyl polymers (e.g., polystyrene, poly(α-methylstyrene), polyvinyltoluene, polyvinylbenzyl chloride, polyvinylbiphenyl, and polyvinylnaphthalene); polyolefins (e.g., polyethylene and polypropylene); poly(halogenated polyolefins) (e.g., polyvinyl chloride and polytetrafluoroethylene); nitrile polymers (e.g., polyacrylonitrile); and (meth)acrylic polymers (e.g., polymethyl methacrylate, polyglycidyl methacrylate, and polyethyl acrylate). The organic polymer material may be a polymer obtained by copolymerizing a single vinyl monomer and a crosslinking agent, a polymer obtained by polymerizing multiple vinyl monomers and a crosslinking agent, or a blend of two or more polymers. Examples of the porous starch include TEXTAID® A from Ingredion. Examples of the dextrin include starch hydrolyzates from Matsutani Chemical Industry Co., Ltd. Examples of the cellulose include spherical cellulose particles (Viscopal) manufactured by Rengo Co., Ltd. and Celluflow (trademark) C-25 manufactured by JNC Corporation. One type of porous body may be used, or multiple types may be used in combination.Since odor-causing components and pigment components contained in the oil-soluble extract can be efficiently reduced, it is preferable to use the inorganic porous material and the organic porous material as the porous material, and it is more preferable to use the silica, the magnesia, and / or the silica-magnesia together with the activated carbon.

[0023] When multiple porous bodies are used, the order in which the multiple porous bodies are contacted with the oil-soluble extract in the contacting step is not particularly limited. For example, each porous body may be contacted with the oil-soluble extract sequentially, or each porous body may be contacted with the oil-soluble extract simultaneously.

[0024] The amount of the porous material added in the contacting step is not particularly limited, and can be set, for example, to an amount that can reduce odor-causing components and coloring matter contained in the oil-soluble composition, depending on the adsorption characteristics of the porous material. Specifically, in the contacting step, the porous material is preferably used in an amount of, for example, 5 to 60 wt %, 5 to 25 wt %, or 10 to 15 wt %, based on the total weight of the mixture after contact. Specifically, when the porous material is silica magnesia, the amount is preferably used in an amount of, for example, 5 to 60 wt %, 5 to 20 wt %, or 5 to 10 wt %, based on the total weight of the mixture after contact. When the porous material is activated carbon, the amount is preferably used in an amount of, for example, 5 to 60 wt %, 3 to 20 wt %, 3 to 10 wt %, or 3 to 5 wt %, based on the total weight of the mixture after contact.

[0025] In the contacting step, when the organic solvent is added, the volume (V Ｅ ) and the volume of the organic solvent (V Ｏ ) and the volume ratio (V Ｏ / V Ｅ The volume ratio (V) is not particularly limited as long as the oil-soluble extract and the organic solvent can be stirred together, and may be, for example, 1 / 1 or more, or 1 / 2 or more. Ｏ / V Ｅ ) is preferably 1 / 1 to 4 / 1, or 1 / 2 to 4 / 1, for example, from the viewpoint of cost.

[0026] The contact conditions (temperature, time, etc.) in the contacting step are not particularly limited, as long as they allow the oil-soluble extract and the porous body to be mixed, preferably uniformly mixed. The contact temperature is, for example, 10 to 30°C, 20 to 25°C, or 25°C. The lower limit of the contact time is, for example, 10 minutes or more, more preferably 15 minutes or more, and even more preferably 30 minutes or more. The upper limit of the contact time is, for example, 24 hours or less, more preferably 16 hours or less.

[0027] In the contacting step, for example, further mixing may be performed after the contacting step. The mixing may be performed using a stirring device such as a vortex mixer, by inversion mixing, or by ultrasonic treatment.

[0028] When the organic solvent is added in the contacting step, the production method of the present disclosure may further include a removal step of removing the organic solvent from the organic solvent and the oil-soluble extract after contact with the porous body. The removal step can be carried out, for example, by treating the oil-soluble extract after contact with the organic solvent and the porous body under reduced pressure to remove the organic solvent. The removal under reduced pressure is not particularly limited as long as it can remove the organic solvent, and can be carried out, for example, by vacuum distillation.

[0029] The reduced pressure conditions (degree of vacuum) are not particularly limited as long as they are conditions that allow the organic solvent to be removed, and can be set depending on the type of the organic solvent. －６ Mpa to -1 x 10 －１ Mpa, or -3 x 10 －５ Mpa to -1 x 10 －１ It is Mpa.

[0030] The removal step may be carried out, for example, while stirring the mixture of the oil-soluble extract and the organic solvent. The stirring speed is preferably adjusted so as not to scatter the mixture in a container containing the mixture of the organic solvent, the porous body, and the oil-soluble extract.

[0031] The conditions (temperature, time, etc.) in the removal step are not particularly limited as long as they allow the organic solvent to be removed, and can be appropriately set depending on the type of organic solvent. The temperature in the removal step is, for example, −10° C. to 130° C., or −4° C. to 121° C. The lower limit of the time in the removal step is, for example, 10 minutes or more, 20 minutes or more, 30 minutes or more, 1 hour or more, or 8 hours or more, and the upper limit of the time in the removal step is, for example, 36 hours or less, 24 hours or less, or 16 hours or less.

[0032] In the manufacturing method of the present disclosure, after the contacting step, a solid-liquid separation step is carried out in which the oil-soluble extract and the porous body are subjected to solid-liquid separation to recover an oily composition. When the manufacturing method of the present disclosure includes the removal step, the solid-liquid separation step may be carried out on the oil-soluble extract after the removal step. In the manufacturing method of the present disclosure, for example, the solid-liquid separation step separates the porous body carrying odor-causing components and pigment components from the mixture of the oil-soluble extract and the porous body, thereby obtaining an oily composition with reduced odor-causing components and pigment components. The solid-liquid separation step can be carried out by a known solid-liquid separation method, such as solid-liquid separation using a separation membrane, filter, or filtration with an appropriate molecular weight cutoff.

[0033] The conditions (temperature, time, etc.) for the solid-liquid separation step are not particularly limited as long as they allow solid-liquid separation of the oil-soluble extract and the porous body. The temperature for the solid-liquid separation step is, for example, 10 to 30°C, 20 to 25°C, or 25°C. The time for the solid-liquid separation step is, for example, 10 minutes or more, or 20 minutes or more.

[0034] The production method of the present disclosure may further include a step of concentrating the recovered oily composition under reduced pressure (vacuum concentration step) after the solid-liquid separation step. The vacuum concentration step can be performed by a known vacuum concentration method, specifically, using an evaporator or the like.

[0035] The conditions (temperature, time, etc.) for the vacuum concentration step are not particularly limited as long as they allow the oily composition to be concentrated. The temperature for the vacuum concentration step is, for example, 20 to 110°C, 30 to 100°C, 40 to 95°C, or 50 to 90°C. The time for the vacuum concentration step is, for example, 10 minutes or more, or 20 minutes or more.

[0036] In the production method of the present disclosure, the color of the oily composition concentrated under reduced pressure may be measured after the vacuum concentration step. The color of the oily composition can be measured by measuring the absorbance at a wavelength of 470 nm. The oily composition can be evaluated as having reduced pigments when the absorbance at 470 nm of the oil-soluble extract used to produce the oily composition is reduced by, for example, 10% or less, 20% or less, 30% or less, 40% or less, 50% or less, 60% or less, 70% or less, 80% or less, 90% or less, 95% or less, or 99% or less, based on the absorbance at 470 nm of the oil-soluble extract used to produce the oily composition.

[0037] In the production method of the present disclosure, after the vacuum concentration step, the odor of the vacuum-concentrated oily composition may be measured. The odor of the oily composition can be measured, for example, by human sensory evaluation (e.g., sensory evaluation of eau de toilette (J. Soc. Cosmet. Chem. Japan. Vol. 33, No. 1 1999, pp. 3-15)) or using an analytical instrument (e.g., gas chromatography).

[0038] Next, examples of the present disclosure will be described. However, the present disclosure is not limited to the following examples. Commercially available reagents were used according to their protocols unless otherwise specified. Note that "mol / l" may also be abbreviated as "M."

[0039] Example 1 An oily composition with reduced odor and pigments could be produced by the method for producing an oily composition according to the present disclosure.

[0040] (1) Preparation of Oily Composition: 100 g of ethanol was added to 20 g of bakuchiol (Varion) and stirred until homogenous. After stirring, 5 g of Shirasagi A and 10 g of Mizuka Fine SM200 were added sequentially and stirred. After stirring, the resulting mixture was subjected to a reduced pressure treatment at -0.094 to -0.095 MPa for 20 minutes while stirring using an aspirator and a stir bar to remove the ethanol. The reduced pressure treatment was performed while adjusting the stirring speed and degree of pressure reduction to prevent scattering of the mixture during the initial stage of the reduced pressure degassing. After confirming that the mixture was almost free of foaming and scattering during the reduced pressure treatment, the mixture was stirred overnight at room temperature (15°C to 25°C (Yakusei-Hatsu No. 0325-1, March 25, 2021, Director-General of the Environmental Health Bureau, Ministry of Health, Labour and Welfare, Standards for Quasi-drug Ingredients 2021)). Next, the mixture after vacuum distillation was subjected to solid-liquid separation using filter paper (Advantec Toyo, filter paper No. 26) and a membrane filter (Advantec Toyo, cellulose acetate, pore size 0.45 μm). In the solid-liquid separation, an appropriate amount of ethanol was used for co-washing. The filtrate obtained by the solid-liquid separation was then concentrated under reduced pressure using an evaporator. The vacuum concentration was carried out at 60-70°C, and the final drying was carried out at 70-80°C. The obtained oily composition was weighed, and the recovery rate of bakuchiol was 93.90%. Furthermore, a sensory evaluation (5-point scale) of the eau de toilette described in the literature (J. Soc. Cosmet. Chem. Japan. Vol. 33, No. 1 1999, pp. 3-15) was conducted, and it was found that the oily composition had a reduced odor compared to the bakuchiol used in its production.

[0041] (2) Color Study of Oily Compositions The color of the oily compositions obtained by the manufacturing method of the present disclosure was studied. Visual inspection revealed that the oily compositions obtained by the manufacturing method of the present disclosure were lighter in color than the bakuchiol used in the manufacturing method. Therefore, 1 g of the oily composition obtained in Example 1(1) or the bakuchiol (control) used in the manufacturing method of Example 1(1) was diluted to 100 ml with 2-propanol for spectroscopic analysis, and the absorbance at 470 nm was measured. The absorbance of the control was 0.051, while the absorbance of the oily composition obtained by the manufacturing method of the present disclosure was 0.02. These results demonstrate that the manufacturing method of the present disclosure can produce oily compositions with improved color.

[0042] Although the present disclosure has been described above with reference to embodiments and examples, the present disclosure is not limited to the above embodiments and examples. Various modifications that can be understood by a person skilled in the art can be made to the configuration and details of the present disclosure within the scope of the present disclosure.

[0043] The patents, patent applications, and publications cited herein are incorporated by reference into this specification in their entirety as if the contents were specifically set forth herein.

[0044] This application claims priority based on Japanese Patent Application No. 2024-094312, filed June 11, 2024, the disclosure of which is incorporated herein in its entirety by reference.

[0045] <Appendix> Some or all of the above embodiments and examples can be described as, but are not limited to, the following appendixes. <Method for producing an oily composition> (Appendix 1) A method for producing an oily composition, comprising: a contacting step of bringing a plant-derived oil-soluble extract into contact with a porous body; and a solid-liquid separation step of performing solid-liquid separation between the oil-soluble extract and the porous body to recover an oily composition. (Appendix 2) The method according to Appendix 1, wherein the contacting step is a contacting step of bringing the oil-soluble extract into contact with an organic solvent and the porous body, and further comprising a removal step of treating the oil-soluble extract after contact with the organic solvent and the porous body under reduced pressure to remove the organic solvent. (Appendix 3) The method according to Appendix 1 or 2, wherein the plant is Dutch ibis (Psoralea corylifolia). (Appendix 4) The method according to any of Appendices 1 to 3, wherein the plant-derived oil-soluble extract contains bakuchiol. (Appendix 5) The manufacturing method according to any one of Appendices 1 to 4, wherein the porous body is an inorganic porous body and / or an organic porous body. (Appendix 6) The manufacturing method according to Appendices 5, wherein the inorganic porous body is a porous body composed of silica (silicon dioxide), magnesia (magnesium oxide), alumina (aluminum oxide), zeolite, or a mixture thereof, or porous silicon. (Appendix 7) The manufacturing method according to Appendices 5, wherein the organic porous body is activated carbon, an organic polymer material, porous starch, dextrin, or cellulose. (Appendix 8) The manufacturing method according to any one of Appendices 2 to 7, wherein the organic solvent is methanol, ethanol, butyrol, propanol, phenoxyethanol, ethyl acetate, butyl acetate, hexane, and / or cyclohexane. (Appendix 9) The manufacturing method according to any one of Appendices 2 to 7, wherein the volume (V Ｅ ) and the volume of the organic solvent (V Ｏ ) and the volume ratio (V Ｏ / V Ｅ ) is 1 / 2 or more. (Supplementary Note 10) The manufacturing method according to any one of Supplementary Note 2 to 9, wherein the removing step is carried out at -4°C to 121°C. (Supplementary Note 11) The reduced pressure condition is -3 x 10 －６ Mpa to -1 x 10 －１The production method according to any one of Appendices 2 to 10, wherein the solid-liquid separation is performed by filtration. (Appendix 12) The production method according to any one of Appendices 1 to 11, wherein the solid-liquid separation is performed by filtration. (Appendix 13) The production method according to any one of Appendices 1 to 12, comprising a step of concentrating under reduced pressure after the solid-liquid separation step. (Appendix 14) The production method according to Appendices 13, wherein the concentration under reduced pressure is performed at 50 to 90°C.

[0046] As described above, the present disclosure can provide a method for producing an oily composition with reduced odor and pigment, etc. Therefore, the present disclosure can be said to be extremely useful, for example, in the field of cosmetics.

Claims

1. A method for producing an oily composition, comprising: a contacting step of contacting a plant-derived oil-soluble extract with a porous body; and a solid-liquid separation step of performing solid-liquid separation between the oil-soluble extract and the porous body to recover an oily composition.

2. The method according to claim 1, wherein the contacting step is a step of contacting the oil-soluble extract with an organic solvent and the porous body, and further comprises a removal step of treating the oil-soluble extract after contact with the organic solvent and the porous body under reduced pressure conditions to remove the organic solvent.

3. The method of claim 1 or 2, wherein the plant is Psoralea corylifolia.

4. The method of any one of claims 1 to 3, wherein the plant-derived oil-soluble extract contains bakuchiol.

5. A manufacturing method according to any one of claims 1 to 4, wherein the porous body is an inorganic porous body and / or an organic porous body.

6. The manufacturing method according to claim 5, wherein the inorganic porous body is a porous body composed of silica (silicon dioxide), magnesia (magnesium oxide), alumina (aluminum oxide), zeolite, or a mixture thereof, or porous silicon.

7. The method of claim 5, wherein the organic porous material is activated carbon, an organic polymer material, porous starch, dextrin, or cellulose.

8. The process according to any one of claims 2 to 7, wherein the organic solvent is methanol, ethanol, butyrol, propanol, phenoxyethanol, ethyl acetate, butyl acetate, hexane, and / or cyclohexane.

9. The volume of the oil-soluble extract (V Ｅ ) and the volume of the organic solvent (V Ｏ ) and the volume ratio (V Ｏ / V Ｅ 9. The method according to claim 2, wherein the ratio of the total weight of the polymer to the total weight of the cellulose ester to the total weight of the polymer is 1 / 2 or more.

10. A method according to any one of claims 2 to 9, wherein the removal step is carried out at a temperature of -4°C to 121°C.

11. The pressure reduction condition is -3 x 10 －６ Mpa to -1 x 10 －１ The method of any one of claims 2 to 10, wherein the temperature is 1000°C or 2000°F.

12. The method of any one of claims 1 to 11, wherein the solid-liquid separation is performed by filtration.

13. The method of any one of claims 1 to 12, further comprising a step of concentrating under reduced pressure after the solid-liquid separation step.

14. The method of claim 13, wherein the vacuum concentration is carried out at 50 to 90°C.

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