Cosmetic composition

Abstract

Provided are: a novel transdermal penetration inhibitor for an oily component such as an ultraviolet absorber and / or a preservative having a logP value of 2.0 or more; and the novel transdermal penetration inhibitor. A cosmetic composition containing a polymer having a structure represented by formula (1) and an oily component, in which R1, R2, and R3 are each independently a hydrogen atom or a C1-4 alkyl group, A is a C2-4 alkylene group, m and n are each independently 1.0-50, the number average molecular weight of the polymer is 10,000 or less, the IOB value of the polymer is 0.4-1.8, and n is an integer of 1-5. And the oily component is an ultraviolet absorber and / or a preservative having a logP value of 2.0 or more. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a cosmetic composition. Background Art

[0002] Oil components such as ultraviolet absorbers and preservatives are formulated in various cosmetics. Such oil components are preferably retained on the skin surface without penetrating into the subcutaneous tissue as much as possible.

[0003] For example, Patent Document 1 discloses a cosmetic that can inhibit the percutaneous penetration of a specific ultraviolet absorber (e.g., octyl methoxycinnamate). More specifically, the cosmetic of Patent Document 1 is a cosmetic containing octyl methoxycinnamate and polypropylene glycol having a number-average molecular weight of 500 to 2,500 (except for a cleansing cosmetic containing polypropylene glycol butyl ether).

[0004] Prior Art Documents

[0005] Patent Documents

[0006] Patent Document 1: Japanese Patent Application Laid-Open No. 2002-284622 Summary of the Invention

[0007] Problems to be Solved by the Invention

[0008] However, there is still room for improvement in the inhibition of percutaneous penetration not only of octyl methoxycinnamate but also of other ultraviolet absorbers and preservatives.

[0009] The present invention aims to improve the above situation, and an object thereof is to provide a new percutaneous penetration inhibitor for oil components such as ultraviolet absorbers and / or preservatives having a logP value of 2.0 or more, and a cosmetic composition containing the new percutaneous penetration inhibitor.

[0010] Means for Solving the Problems

[0011] The present invention for achieving the above object is as follows.

[0012] <Aspect 1>

[0013] A cosmetic composition comprising a polymer having a structure represented by the following formula (1) and an oil component,

[0014]

[0015] In the above formula (1), R 1 , R 2 and R 3 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, A is an alkylene group having 2 to 4 carbon atoms, and m and n are each independently 1.0 to 50,

[0016] The number-average molecular weight of the above-mentioned polymer is 10,000 or less,

[0017] the IOB value of the above-mentioned polymer is 0.4 to 1.8, and

[0018] the above-mentioned oily component is an ultraviolet absorber and / or a preservative having a logP value of 2.0 or more.

[0019] 〈Embodiment 2〉

[0020] For the composition according to Embodiment 1, in the above formula (1), A is represented by the following formula (2),

[0021]

[0022] In the above formula (2), R 4 is an alkyl group having 1 or 2 carbon atoms.

[0023] 〈Embodiment 3〉

[0024] For the composition according to Embodiment 1 or 2, the above-mentioned polymer is a random copolymer.

[0025] 〈Embodiment 4〉

[0026] For the composition according to any one of Embodiments 1 to 3, in the above formula (1), m is 2 or more, and at least a part of R 1 is methyl.

[0027] 〈Embodiment 5〉

[0028] For the composition according to any one of Embodiments 1 to 4, in the above formula (1), at least one of R 2 and R 3 is methyl.

[0029] 〈Embodiment 6〉

[0030] For the composition according to any one of Embodiments 1 to 5, the logP value of the above-mentioned oily component is 15.0 or less.

[0031] 〈Embodiment 7〉

[0032] For the composition according to any one of Embodiments 1 to 6, the above-mentioned polymer is a percutaneous penetration inhibitor of the above-mentioned oily component.

[0033] 〈Embodiment 8〉

[0034] An application is an application of a polymer having a structure represented by the following formula (1) as a percutaneous penetration inhibitor of an ultraviolet absorber and / or a preservative, that is, an oily component, having a logP value of 2.0 or more,

[0035]

[0036] In the above formula (1), R 1 , R 2 and R 3 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, A is an alkylene group having 2 to 4 carbon atoms, and m and n are each independently 1.0 to 50,

[0037] The number average molecular weight of the above polymer is 10,000 or less, and

[0038] The IOB value of the above polymer is 0.4 to 1.8.

[0039] <Solution 9>

[0040] In the application according to Solution 8, in the above formula (1), A is represented by the following formula (2),

[0041]

[0042] In the above formula (2), R 4 is an alkyl group having 1 or 2 carbon atoms.

[0043] <Solution 10>

[0044] In the application according to Solution 8 or 9, the above polymer is a random copolymer.

[0045] <Solution 11>

[0046] In the application according to any one of Solutions 8 to 10, in the above formula (1), m is 2 or more, and at least a part of R 1 is methyl.

[0047] <Solution 12>

[0048] In the application according to any one of Solutions 8 to 11, in the above formula (1), at least one of R 2 and R 3 is methyl.

[0049] <Solution 13>

[0050] In the application according to any one of Solutions 8 to 12, the logP value of the above oil component is 15.0 or less.

[0051] Effects of the Invention

[0052] According to the present invention, a new percutaneous penetration inhibitor for oil components such as ultraviolet absorbers and / or preservatives having a logP value of 2.0 or more, and the new percutaneous penetration inhibitor can be provided. Brief Description of the Drawings

[0053] Figure 1A graph showing the amount of adsorption to the stratum corneum (stratum corneum stratification) of the composition samples of Example 1, Example 2, and Comparative Example 1.

[0054] Figure 2 A graph showing the amount of adsorption to the stratum corneum (average of the total of all layers of the stratum corneum) of the composition samples of Example 1, Example 2, and Comparative Example 1.

[0055] Figure 3 A graph showing the amount of adsorption to the stratum corneum (stratum corneum stratification) of the composition samples of Example 3 and Comparative Example 2.

[0056] Figure 4 A graph showing the amount of adsorption to the stratum corneum (average of the total of all layers of the stratum corneum) of the composition samples of Example 3 and Comparative Example 2.

[0057] Figure 5 A graph showing the amount of adsorption to the stratum corneum (stratum corneum stratification) of the composition samples of Example 4 and Comparative Example 3.

[0058] Figure 6 A graph showing the amount of adsorption to the stratum corneum (average of the total of all layers of the stratum corneum) of the composition samples of Example 4 and Comparative Example 3. Detailed Description of the Embodiment

[0059] Hereinafter, the embodiments of the present invention will be described in detail. It should be noted that the present invention is not limited to the following embodiments, and various modifications can be made within the scope of the intention of the invention.

[0060] <<Cosmetic Composition>>

[0061] The cosmetic composition of the present invention (hereinafter, also simply referred to as "the composition of the present invention") is the following composition.

[0062] It is a cosmetic composition containing a polymer having a structure represented by the following formula (1) and an oily component.

[0063]

[0064] In formula (1), R 1 , R 2 and R 3 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, A is an alkylene group having 2 to 4 carbon atoms, and m and n are each independently 1.0 to 50.

[0065] The number average molecular weight of the polymer is 10,000 or less.

[0066] The IOB value of the polymer is 0.4 to 1.8, and

[0067] The oily component is an ultraviolet absorber and / or a preservative having a logP value of 2.0 or more.

[0068] The composition of the present invention contains the polymer of the present invention described below. The polymer of the present invention has an effect of suppressing the permeability of a specific oily component (i.e., an oily component which is an ultraviolet absorber and / or a preservative having a logP value of 2.0 or more) into the skin. Therefore, the polymer of the present invention can also be said to be a percutaneous penetration inhibitor of such a specific oily component. In other words, the polymer of the present invention can be used as a percutaneous penetration inhibitor of such a specific oily component contained in the composition of the present invention.

[0069] Although not limited by theory, it is presumed that this is due to the characteristics of the polymer of the present invention, namely, the unique structure represented by formula (1), the number average molecular weight in a specific range (10,000 or less), and the IOB (Inorganic Organic Balance) value in a specific range (0.4 to 1.8).

[0070] In addition, it is considered that the polymer of the present invention is amphiphilic due to its unique structure. It is presumed that the polymer of the present invention exhibits an effect of retaining a specific oily component (i.e., an oily component which is an ultraviolet absorber and / or a preservative having a logP value of 2.0 or more) on the surface of the skin due to this amphiphilicity. In other words, it is presumed that the permeability of the specific oily component into the skin becomes low by using it in combination with the polymer of the present invention.

[0071] <The polymer of the present invention>

[0072] The polymer of the present invention has a structure represented by the following formula (1):

[0073]

[0074] In formula (1), R 1 , R 2 and R 3 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. It should be noted that in the present invention, examples of the alkyl group having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl. In addition, as long as the effects of the present invention are not impaired, these alkyl groups may further have substituents. The substituents are not particularly limited, and examples thereof include halogenated groups.

[0075] According to one embodiment of the present invention, in formula (1), R 1 , R 2 and R 3 can each independently be a hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, or tert-butyl.

[0076] According to an embodiment of the present invention, in formula (1), R 1 is preferably a hydrogen atom, a methyl group or an ethyl group. Further, when m is 2 or more, that is, when there are a plurality of Rs 1 each R 1 may be the same or different. In particular, at least a part of R 1 is preferably a methyl group. When at least a part of R 1 is a methyl group, for example, it is preferable from the viewpoint of improving the usability of the composition of the present invention.

[0077] According to an embodiment of the present invention, in formula (1), R 1 may also be a state in which a hydrogen atom and an alkyl group having 1 to 4 carbon atoms are mixed. That is, a part of R 1 may be a hydrogen atom and another part may be an alkyl group having 1 to 4 carbon atoms. Preferably, a part of R 1 is a hydrogen atom and another part is a methyl group.

[0078] According to an embodiment of the present invention, in formula (1), R 2 is preferably a hydrogen atom, a methyl group or an ethyl group, and more preferably a methyl group in particular.

[0079] According to an embodiment of the present invention, in formula (1), R 2 may also be a state in which a hydrogen atom and an alkyl group having 1 to 4 carbon atoms are mixed. That is, a part of R 2 may be a hydrogen atom and another part may be an alkyl group having 1 to 4 carbon atoms. Preferably, a part of R 2 is a hydrogen atom and another part is a methyl group.

[0080] According to an embodiment of the present invention, in formula (1), R 3 is preferably a hydrogen atom, a methyl group or an ethyl group, and more preferably a methyl group in particular.

[0081] According to an embodiment of the present invention, in formula (1), preferably at least one of R 2 and R 3 is a methyl group.

[0082] In formula (1), A is an alkylene group having 2 to 4 carbon atoms. More specifically, A may be, for example, ethylene, propylene, butylene, isobutylene, etc., but is not limited to these. In particular, A is preferably represented by the following formula (2):

[0083]

[0084] In formula (2), R 4is an alkyl group having 1 or 2 carbon atoms. More specifically, R 4 may be a methyl group or an ethyl group.

[0085] In formula (1), m and n represent the average number of moles of addition of each structural unit. m and n are each independently from 1.0 to 50. More specifically, they may be 1.0 or more, 1.5 or more, 2.0 or more, 3.0 or more, 4.0 or more, 5.0 or more, 6.0 or more, 7.0 or more, 8.0 or more, 9.0 or more, or 10 or more. In addition, they may be 50 or less, 45 or less, 40 or less, 35 or less, 34 or less, 32 or less, 30 or less, 28 or less, 26 or less, 25 or less, 24 or less, 22 or less, 20 or less, 18 or less, 16 or less, 15 or less, 14 or less, 12 or less, 10 or less, or 5.0 or less.

[0086] In addition, in formula (1), m is preferably 1.0 or more and 14 or less, more preferably 2.0 or more and 5.0 or less. In addition, in formula (1), n is preferably 2.0 or more and 34 or less, more preferably 6.0 or more and 12 or less.

[0087] According to one embodiment of the present invention, in formula (1), m + n may be 4.0 or more, 4.5 or more, 5.0 or more, 6.0 or more, 7.0 or more, 8.0 or more, 9.0 or more, 10 or more, 11 or more, 12 or more, 13 or more, 14 or more, or 15 or more. In addition, it may be 50 or less, 45 or less, 40 or less, 35 or less, 30 or less, 25 or less, 20 or less, 15 or less, or 12 or less.

[0088] According to one embodiment of the present invention, in formula (1), m:n may be from 1:10 to 10:1.

[0089] The number-average molecular weight of the polymer of the present invention is 10,000 or less. More specifically, the number-average molecular weight of the polymer of the present invention can be, for example, 10,000 or less, 5,000 or less, 3,500 or less, 3,200 or less, 3,000 or less, 2,800 or less, 2,500 or less, 2,200 or less, 2,000 or less, 1,800 or less, 1,500 or less, 1,400 or less, 1,300 or less, 1,200 or less, 1,100 or less, 1,000 or less, 900 or less, 800 or less, 700 or less, or 600 or less. In addition, it can be 130 or more, 150 or more, 200 or more, 250 or more, 300 or more, 350 or more, 400 or more, 450 or more, 500 or more, 550 or more, 600 or more, 650 or more, 700 or more, 750 or more, 800 or more, 850 or more, 900 or more, 950 or more, or 1,000 or more. In addition, the number-average molecular weight of the polymer of the present invention is preferably 300 or more and 3,500 or less, more preferably 500 or more and 1,200 or less.

[0090] The IOB value of the polymer of the present invention is 0.4 to 1.8. More specifically, the IOB value of the polymer of the present invention can be, for example, 0.4 or more, 0.5 or more, 0.6 or more, 0.7 or more, 0.8 or more, 0.9 or more, or 1.0 or more. In addition, it can be 1.8 or less, 1.6 or less, 1.4 or less, or 1.2 or less. In addition, the IOB value of the polymer of the present invention is preferably 0.7 or more and 1.2 or less.

[0091] Here, the IOB value is an abbreviation of Inorganic / Organic Balance (inorganic / organic ratio), and is a value representing the ratio of the inorganic value to the organic value, and is an index representing the degree of polarity of an organic compound. Specifically, the IOB value is expressed as IOB value = inorganic value / organic value. Regarding each of the "inorganic value" and "organic value", for example, the "inorganic value" and "organic value" corresponding to various atoms or functional groups are set in such a way that the "organic value" is 20 for one carbon atom in the molecule and the "inorganic value" is 100 for one hydroxyl group. By accumulating the "inorganic value" and "organic value" of all atoms and functional groups in the organic compound, the IOB value of the organic compound can be calculated (see, for example, Yoshio Koda, "Organic Concept Map - Basics and Applications -", p. 11-17, Sankyo Publishing, issued in 1984). It should be noted that regarding the method for determining the IOB value, the method described in the examples can be referred to.

[0092] The polymer of the present invention can be a block copolymer or a random copolymer, but a random copolymer is preferred.

[0093] The method for producing the polymer of the present invention is not particularly limited. For example, it is preferably carried out by addition polymerization of epoxides corresponding to each structural unit. In addition, the addition polymerization can be block polymerization or random polymerization, but random polymerization is preferred.

[0094] Furthermore, the method for producing the polymer of the present invention may further comprise: further reacting a haloalkane with the polymer obtained by the above addition polymerization. Through the reaction with the haloalkane, the hydroxyl groups in the molecule of the resulting polymer are blocked by alkyl groups, and as a result, the overall hydrophobicity of the polymer can be adjusted as desired. In the present invention, in the molecule of the polymer, the blocking rate of the hydroxyl groups by alkyl groups can be, for example, 30% or more, 35% or more, 40% or more, 45% or more, 50% or more, or 55% or more, and in addition, it can be 60% or less, 59% or less, 58% or less, 57% or less, 56% or less, or 55% or less. It should be noted that the blocking rate of the hydroxyl groups by alkyl groups can be determined by the method described in the examples.

[0095] As one of the characteristics of the polymer of the present invention, it has both high water solubility and high lipid solubility.

[0096] The solubility of the polymer of the present invention in water can be, for example, 10% by mass or more, 15% by mass or more, 20% by mass or more, 25% by mass or more, 30% by mass or more, 35% by mass or more, 40% by mass or more, 45% by mass or more, or 50% by mass or more.

[0097] In addition, as an index of the lipid solubility of the polymer of the present invention, for example, the solubility in olive oil can be used. The solubility of the polymer of the present invention in olive oil can be, for example, 0.01% by mass or more, 0.05% by mass or more, 0.10% by mass or more, 0.50% by mass or more, or 1.00% by mass or more. It should be noted that the upper limit value of the solubility of the polymer of the present invention in olive oil is not particularly limited and can be, for example, 10% by mass or less.

[0098] In the composition of the present invention, the content of the polymer of the present invention is not particularly limited. For example, it can be 0.001% by mass or more, 0.005% by mass or more, 0.01% by mass or more, 0.05% by mass or more, 0.1% by mass or more, 0.5% by mass or more, 1.0% by mass or more, 2.0% by mass or more, 3.0% by mass or more, 4.0% by mass or more, or 5.0% by mass or more, and in addition, it can be 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, 10% by mass or less, 8.0% by mass or less, 5.0% by mass or less, 3.0% by mass or less, or 1.0% by mass or less.

[0099] In addition, when the polymer of the present invention is used as a percutaneous penetration inhibitor of an ultraviolet absorber and / or a preservative, i.e., an oily component, having a logP value of 2.0 or more, it can be, for example, 1.0 part by mass or more, 5.0 parts by mass or more, 10 parts by mass or more, 20 parts by mass or more, 30 parts by mass or more, 40 parts by mass or more, 50 parts by mass or more, 60 parts by mass or more, 70 parts by mass or more, 80 parts by mass or more, 90 parts by mass or more, or 100 parts by mass or more, based on 100 parts by mass in total of the oily components that are ultraviolet absorbers and / or preservatives having a logP value of 2.0 or more. In addition, it can be 10,000 parts by mass or less, 5,000 parts by mass or less, 1,000 parts by mass or less, 500 parts by mass or less, or 100 parts by mass or less.

[0100] 〈Oily component that is an ultraviolet absorber and / or a preservative having a logP value of 2.0 or more〉

[0101] The composition of the present invention contains a specific oily component. The specific oily component related to the present invention is an ultraviolet absorber and / or a preservative having a logP value of 2.0 or more. It should be noted that in the present invention, the term "preservative" also includes what is generally called "antioxidant".

[0102] It should be noted that here, the so-called "oily component that is an ultraviolet absorber and / or a preservative having a logP value of 2.0 or more" means an ultraviolet absorber having a logP value of 2.0 or more and / or a preservative having a logP value of 2.0 or more.

[0103] In addition, the so-called "logP value" represents the ratio of the equilibrium concentration of a substance dissolved in the two phases of octanol and water, and is an index indicating the hydrophilic-hydrophobic property of the component (non-ionic substance). In particular, it is known that when the logP value is around 2.0, the skin permeability of the component (non-ionic substance) shows a maximum, and when the logP value is less than this, the skin permeability of the component (non-ionic substance) becomes smaller (for example, "Non-formulation Parameters That Affect Penetrant-Skin-Vehicle Interactions and Percutaneous Absorption", written by JE Grice et al., "Percutaneous Penetration Enhancers Drug Penetration Into / Through the Skinpp" (2017), PP. 45 - 75).

[0104] Furthermore, regarding the logP value, for example, the logP values of a large number of compounds published in databases that can be obtained from Daylight Chemical Information Systems, Inc. (Daylight CIS) or PubChem (National Center for Biotechnology Information) etc. can be referred to. In addition, in the case where there is no measured logP value, it can be calculated using a program such as "CLOGP" (Daylight CIS).

[0105] (Ultraviolet absorber with a logP value of 2.0 or more)

[0106] In the present invention, the logP value of the ultraviolet absorber only needs to be 2.0 or more. For example, it can be 2.1 or more, 2.2 or more, 2.3 or more, 2.4 or more, 2.5 or more, 2.6 or more, 2.7 or more, 2.8 or more, 2.9 or more, 3.0 or more, 3.1 or more, 3.2 or more, 3.3 or more, 3.4 or more, 3.5 or more, 3.6 or more, 3.7 or more, 3.8 or more, 3.9 or more, 4.0 or more, 4.1 or more, 4.2 or more, 4.3 or more, 4.4 or more, 4.5 or more, 4.6 or more, 4.7 or more, 4.8 or more, 4.9 or more, 5.0 or more, 5.1 or more, 5.2 or more, 5.3 or more, 5.4 or more, 5.5 or more, 5.6 or more, 5.7 or more, 5.8 or more, 5.9 or more, 6.0 or more, 6.1 or more, 6.2 or more, 6.3 or more, 6.4 or more, 6.5 or more, 6.6 or more, 6.7 or more, 6.8 or more, 6.9 or more, or 7.0 or more. In addition, the upper limit value of the logP value of the ultraviolet absorber is not particularly limited. For example, it can be 15.0 or less, 14.0 or less, 13.0 or less, 12.0 or less, 11.0 or less, 10.0 or less, 9.0 or less, 8.0 or less, 7.0 or less, 6.0 or less, or 5.0 or less.

[0107] In the present invention, specific examples of the ultraviolet absorber with a logP value of 2.0 or more are shown below, but are not limited to these. That is, as the ultraviolet absorber with a logP value of 2.0 or more, for example, octyl methoxycinnamate (logP value: 5.7) and 4-tert-butyl-4'-methoxydibenzoylmethane (logP value: 4.8) etc. can be cited.

[0108] In addition, in the composition of the present invention, the content of the ultraviolet absorber having a logP value of 2.0 or more is not particularly limited. For example, it may be 0.001% by mass or more, 0.005% by mass or more, 0.01% by mass or more, 0.05% by mass or more, 0.1% by mass or more, 0.5% by mass or more, 1.0% by mass or more, 1.5% by mass or more, 2.0% by mass or more, 2.5% by mass or more, 3.0% by mass or more, 3.5% by mass or more, 4.0% by mass or more, 4.5% by mass or more, 5.0% by mass or more, 5.5% by mass or more, 6.0% by mass or more, 6.5% by mass or more, 7.0% by mass or more, or 7.5% by mass or more. In addition, it may be 20% by mass or less, 15% by mass or less, 10% by mass or less, or 8.0% by mass or less.

[0109] (Preservative with a logP value of 2.0 or more)

[0110] In the present invention, the logP value of the preservative only needs to be 2.0 or more. For example, it may be 2.1 or more, 2.2 or more, 2.3 or more, 2.4 or more, 2.5 or more, 2.6 or more, 2.7 or more, 2.8 or more, 2.9 or more, 3.0 or more, 3.1 or more, 3.2 or more, 3.3 or more, 3.4 or more, 3.5 or more, 3.6 or more, 3.7 or more, 3.8 or more, 3.9 or more, 4.0 or more, 4.1 or more, 4.2 or more, 4.3 or more, 4.4 or more, 4.5 or more, 4.6 or more, 4.7 or more, 4.8 or more, 4.9 or more, 5.0 or more, 5.1 or more, 5.2 or more, 5.3 or more, 5.4 or more, 5.5 or more, 5.6 or more, 5.7 or more, 5.8 or more, 5.9 or more, 6.0 or more, 6.1 or more, 6.2 or more, 6.3 or more, 6.4 or more, 6.5 or more, 6.6 or more, 6.7 or more, 6.8 or more, 6.9 or more, or 7.0 or more. In addition, the upper limit value of the logP value of the preservative is not particularly limited. For example, it may be 15.0 or less, 14.0 or less, 13.0 or less, 12.0 or less, 11.0 or less, 10.0 or less, 9.0 or less, 8.0 or less, 7.0 or less, 6.0 or less, or 5.0 or less.

[0111] In the present invention, specific examples of the preservative having a logP value of 2.0 or more are shown below, but are not limited thereto. That is, as the preservative having a logP value of 2.0 or more, for example, ascorbyl palmitate (logP value: 14.0), tocopheryl acetate (logP value: 10.8), butylparaben (logP value: 3.6), resveratrol (logP value: 3.1), ethylparaben (logP value: 2.5), and methylparaben (logP value: 2.0) can be cited.

[0112] In addition, in the composition of the present invention, the content of the preservative having a logP value of 2.0 or more is not particularly limited. For example, it may be 0.001% by mass or more, 0.005% by mass or more, 0.01% by mass or more, 0.05% by mass or more, 0.1% by mass or more, 0.5% by mass or more, or 1.0% by mass or more. In addition, it may be 5.0% by mass or less, 2.0% by mass or less, 1.0% by mass or less, or 0.5% by mass or less.

[0113] 〈Other Components〉

[0114] In addition to the polymer of the present invention and the oily components which are ultraviolet absorbers and / or preservatives having a logP value of 2.0 or more in the composition of the present invention, the composition of the present invention may further contain one or more components which are usually used in skin external preparations such as cosmetics and pharmaceuticals as other components.

[0115] Specific examples of other components include, for example, powder components, oily components other than the above-mentioned oily components which are ultraviolet absorbers and / or preservatives having a logP value of 2.0 or more, liquid oils and fats, solid oils and fats, waxes, hydrocarbons, higher fatty acids, higher alcohols, esters, silicones, anionic surfactants, cationic surfactants, amphoteric surfactants, nonionic surfactants, water-soluble polymers, thickeners, film-forming agents, ultraviolet absorbers, sequestering agents, lower alcohols, polyhydric alcohols, sugars, amino acids, organic amines, polymer emulsions, pH adjusters, skin nutrients, vitamins, antioxidant aids, fragrances, water, etc., but are not limited thereto.

[0116] The dosage form of the composition of the present invention is not particularly limited, and may be, for example, a solution system, a solubilization system, an emulsion system (oil-in-water type or water-in-oil type), a powder dispersion system, a water-oil two-layer system, a water-oil-powder three-layer system, a gel, a mist, a spray, a mousse, a ball or a stick, etc., or may be a preparation such as a sheet impregnated or coated with a non-woven fabric or the like.

[0117] In addition, the product form of the composition of the present invention is not particularly limited, and may be, for example, skin care cosmetics (facial cosmetics) such as lotion, emulsion, cream, mask, etc.; makeup cosmetics such as foundation, base makeup, lipstick, eyeshadow, etc.; sunscreen cosmetics (sunscreen agents); body cosmetics; fragrance cosmetics; skin cleansing agents such as makeup remover, body shampoo, etc.; hair cosmetics such as hair liquid, hair tonic, hair conditioner, shampoo, rinse, hair growth agent, etc.; or ointments, etc.

[0118] 〈Use of the Polymer of the Present Invention〉

[0119] The present invention also provides the use of the polymer of the present invention as a percutaneous penetration inhibitor for the above-mentioned specific oily components (i.e., oily components such as ultraviolet absorbers and / or preservatives having a logP value of 2.0 or more).

[0120] Here, regarding the specific oily components (i.e., oily components such as ultraviolet absorbers and / or preservatives having a logP value of 2.0 or more) and the blending amount thereof when using the polymer of the present invention as a percutaneous penetration inhibitor for the specific oily components, reference may be appropriately made to the item of "the composition of the present invention" above.

[0121] Examples

[0122] The following examples are given to illustrate the present invention in further detail, but the present invention is not limited thereto.

[0123] <<Synthesis Examples 1 and 2>>

[0124] In the following Synthesis Examples 1 and 2, polymers having the structure shown in the following formula (3) were synthesized respectively:

[0125]

[0126] It should be noted that in formula (3), the content within [] is a random copolymer.

[0127] 〈Synthesis Example 1〉

[0128] Synthesis Example 1: R 1 = H, R 2 = H, R 3 = CH3, R 4 = CH3, m = 2.0 and n = 6.0 of Polymer 1

[0129] It was synthesized by the following method to obtain Polymer 1.

[0130] 128 g of methanol and 6.4 g of potassium hydroxide as a catalyst were added to an autoclave. After replacing the air in the autoclave with dry nitrogen, the catalyst was completely dissolved at 80°C with stirring. Next, a mixture of 592 g of glycidol and 1392 g of propylene oxide was added dropwise at 95°C over 20 hours through a dropping device, and then stirred for 5 hours. The reaction composition was taken out from the autoclave, neutralized with hydrochloric acid to make the pH 6 - 7, and treated at -0.095 MPa (50 mmHg) and 100°C for 1 hour to remove the contained water. Further, filtration was carried out to remove the salt generated after the treatment, and 2000 g of Polymer 1 of Synthesis Example 1 was obtained.

[0131] Hereinafter, various physical property values of the obtained Polymer 1 were determined.

[0132] (Number-average molecular weight)

[0133] The number-average molecular weight of the obtained Polymer 1 was calculated by measurement using gel permeation chromatography (GPC). The system was the SHODEX (registered trademark) GPC101 dedicated GPC system, the differential refractive index detector was the SHODEX RI-71s, the guard column was the SHODEX KF-G, and the columns were three HODEX KF804L columns installed continuously. The column temperature was 40°C, and tetrahydrofuran as the eluent was flowed at a rate of 1 ml / min. 0.1 ml of a 0.1 wt% tetrahydrofuran solution of the obtained reaction product was injected, and a chromatogram represented by refractive index intensity and elution time was obtained using the BORWIN GPC calculation program. The number-average molecular weight was determined using polyethylene glycol as a standard from this chromatogram, and the result was approximately 530.

[0134] (Weight-average molecular weight)

[0135] The weight-average molecular weight of the obtained Polymer 1 was determined by GPC calculation in the same manner as above, and was approximately 859.

[0136] (Polydispersity)

[0137] Based on the results of the number-average molecular weight and weight-average molecular weight determined above, the polydispersity Mw / Mn of Polymer 1 was 1.62.

[0138] (IOB value)

[0139] The IOB value of the obtained Polymer 1 was determined as follows, and the result was 1.1.

[0140] More specifically, in Polymer 1, as the organic value, carbon was set to 20 and iso-branches were set to -10 for calculation. In addition, for the inorganic value, hydroxyl groups were set to 100 and ether bonds were set to 20 for calculation.

[0141] · Methanol moiety: (1 carbon atom, 1 hydroxyl group) × 1

[0142] Organic value: 20

[0143] Inorganic value: 100

[0144] · Glycidyl moiety: (3 carbon atoms, 1 iso-branch, 1 hydroxyl group, 1 ether bond) × 2

[0145] Organic value: (60 - 10) × 2 = 100

[0146] Inorganic value: (100 + 20) × 2 = 240

[0147] · Propylene oxide moiety: (3 carbon atoms, 1 iso-branch, 1 ether bond) × 6

[0148] Organic value: (60 - 10) × 6 = 300

[0149] Inorganic value: 20 × 6 = 120

[0150] As described above, since the total organic value is 420 and the total inorganic value is 460, the IOB value is 1.09.

[0151] (Cloud point)

[0152] For the obtained Polymer 1, a 5 wt% aqueous solution was prepared, heated to 85°C, and then cooled. The temperature at which it became a transparent solution was 74°C. Therefore, it was found that the cloud point of Polymer 1 was 74°C.

[0153] (Hydroxyl value)

[0154] The hydroxyl value of the obtained Polymer 1 was measured according to the measurement method of JIS K - 1557 - 1, and the result was 294.

[0155] (Solubility in water)

[0156] The solubility of the obtained Polymer 1 in water was determined in the same manner as the method described later for "compatibility evaluation", and the result was 50 mass% or more.

[0157] (Solubility in olive oil)

[0158] The solubility of the obtained Polymer 1 in olive oil was determined as follows. That is, Polymer 1 was mixed with olive oil so that the concentration became 1.0 wt%, and the appearance was confirmed. If it was uniform, it was designated as "〇". In this case, the solubility of Polymer 1 in olive oil was 1.0 mass%.

[0159] The various physical property values of Polymer 1 measured above are shown in Table 1 below.

[0160] 〈Synthesis Example 2〉

[0161] Synthesis Example 2: R 1 = H and CH3, R 2 = H and CH3, R 3 = CH3, R 4 = CH3, m = 2.0 and n = 6.0 of Polymer 2

[0162] Polymer 2 was synthesized by the following method and obtained.

[0163] 128 g of methanol and 6.4 g of potassium hydroxide as a catalyst were added to an autoclave. After displacing the air in the autoclave with dry nitrogen, the catalyst was completely dissolved at 80 °C with stirring. Next, a mixture of 592 g of glycidol and 1392 g of propylene oxide was added dropwise through a dropping device at 95 °C over 20 hours, and then stirred for 2 hours. Next, 244 g of potassium hydroxide was added, and the inside of the system was displaced with dry nitrogen. After displacing the inside of the system with dry nitrogen, 200 g of chloromethane was pressed in at a temperature of 80 to 130 °C and reacted for 5 hours. Then, the reaction composition was taken out from the autoclave, neutralized with hydrochloric acid to a pH of 6 to 7, and treated at -0.095 MPa (50 mmHg) and 100 °C for 1 hour to remove the contained water. Further, filtration was carried out to remove the salt generated after the treatment, and 1820 g of polymer 2 was obtained. Before reacting chloromethane, a sample was taken, and the hydroxyl value after purification was 125. Therefore, it was known that 2 and R 3 the ratio of methyl group to hydrogen atom (CH3 / H) in was 0.57. That is, the hydroxyl group blocking rate of polymer 2 was 57%.

[0164] In the same manner as in the case of the above polymer 1, various physical property values of the obtained polymer 2 were determined, and the respective results are shown in Table 1 below.

[0165] [Table 1]

[0166] (Table 1 Synthesis Example 1 and Synthesis Example 2)

[0167]

[0168] ※1 Regarding the synthesized compound, it was mixed with olive oil so that the concentration became 1.0 mass%, and the appearance was confirmed. If it was uniform, it was designated as "○".

[0169] 〈Compatibility Evaluation〉

[0170] The above-synthesized polymers 1 and 2 were mixed with water and various oils at a certain concentration, stirred, and then left standing for 1 day. The compatibility of each was investigated by visual observation. The results are shown in Table 1-2 below. It should be noted that in Table 2, "〇" indicates "compatible" and "×" indicates "insoluble".

[0171] [Table 1-2]

[0172] (Table 1-2)

[0173]

[0174] 《Examples 1 and 2, and Comparative Example 1》

[0175] Based on the formulation in Table 2, the cosmetic compositions (water-in-oil sunscreen) of the examples and comparative examples were each prepared by a conventional method. The "human stratum corneum adsorption test" was conducted on each of the prepared compositions. It should be noted that the values in Table 2 represent the blending amounts of the respective components, with the unit being mass%.

[0176] [Table 2]

[0177] (Table 2: Examples 1 and 2, and Comparative Example 1)

[0178]

[0179] ※|: "Octyl methoxycinnamate": Trade name: Parsol MCX; Manufactured by DSM Nutritional Products Japan Co., Ltd.

[0180] 〈Human stratum corneum adsorption test〉

[0181] In the laboratory, the inner sides of the forearms of the subjects were washed once with soap. After wiping the washed area with a towel to dry it, the subjects were made to wait in the laboratory for 15 minutes. On the inner sides of the forearms, the test samples of each composition were applied at a ratio of 2 μL / cm 2 . Here, the allocation of the application sites of each test sample was randomly rotated. Further, 6 hours after applying the test sample, the application site was washed once with soap to remove the test sample adsorbed on the skin surface. After the subjects were made to wait in the laboratory for 15 minutes, the stratum corneum of the area where the test sample was applied was collected 6 times (6 layers) by tape stripping. After quantifying the protein amount in the stratum corneum collected with each tape, out of the 6 tapes of 6 layers, 2 tapes of 2 layers were sequentially taken from the upper layer, and while immersing such 2 tapes in 2 mL of a solvent (a mixed solvent containing water and methanol in a 1:1 ratio), ultrasonic irradiation was performed for 15 minutes, and it was stored overnight at 37°C to extract the drug from the tape. The extract was collected from the storage solution, and the amount of the drug was quantified using an Agilent G6120 HPLC system equipped with an LC-MS detector, and the stratum corneum adsorption amount per stratum corneum protein for 2 layers was calculated respectively. The calculated results are shown in Figure 1 . In addition, Figure 2 is a graph showing the stratum corneum adsorption amount per stratum corneum protein in all layers from stratum corneum 1 to 6 of the composition test samples of each example and comparative example.

[0182] From Figure 1 and Figure 2 results, it is clearly known that the stratum corneum adsorption amounts of the ultraviolet absorbers in Example 1 containing Polymer 1 and Example 2 containing Polymer 2 are both lower than those in Comparative Example 1 which does not contain the polymer of the present invention.

[0183] In other words, it can be understood that in Example 1 and Example 2, by containing Polymer 1 and Polymer 2 respectively, the percutaneous penetration of octyl methoxycinnamate (logP value: 5.7) as an ultraviolet absorber was inhibited. From this result, it is implied that the polymer of the present invention can be used as a percutaneous penetration inhibitor of octyl methoxycinnamate (logP value: 5.7) as an ultraviolet absorber.

[0184] 《Example 3 and Comparative Example 2》

[0185] Based on the formulations in Table 3, the cosmetic compositions of Example 3 and Comparative Example 2 were prepared. The above-mentioned "human stratum corneum adsorption test" was conducted on each of the prepared compositions. The results are shown in Figure 3 and Figure 4 . It should be noted that Figure 3 is a graph showing the results of separately calculating the stratum corneum adsorption amount per stratum corneum protein in 2 portions, Figure 4 is a graph showing the stratum corneum adsorption amount per stratum corneum protein in all layers of stratum corneum 1 to 6.

[0186] [Table 3]

[0187] (Table 3, Example 3 and Comparative Example 2)

[0188]

[0189] It should be noted that the values in Table 3 refer to the blending amounts of the respective components, and the unit is mass%.

[0190] From Figure 3 and Figure 4 's results, it is clearly understood that the stratum corneum adsorption amount of the preservative (butylparaben) in Example 3 containing Polymer 1 is lower than that in Comparative Example 2 which does not contain the polymer of the present invention.

[0191] In other words, it can be understood that in Example 3, by containing Polymer 1, the percutaneous penetration of butylparaben (logP value: 3.6) as a preservative was inhibited. From this result, it is implied that the polymer of the present invention can be used as a percutaneous penetration inhibitor of butylparaben (logP value: 3.6) as a preservative.

[0192] 《Example 4 and Comparative Example 3》

[0193] Based on the formulations in Table 4, the cosmetic compositions of Example 4 and Comparative Example 3 were prepared. The above-mentioned "human stratum corneum adsorption test" was conducted on each of the prepared compositions. The results are shown in Figure 5 and Figure 6 . It should be noted that Figure 5 is a graph showing the results of separately calculating the stratum corneum adsorption amount per stratum corneum protein in 2 portions, Figure 6A graph showing the amount of stratum corneum adsorbed by each stratum corneum protein in all 1 to 6 layers of the stratum corneum.

[0194] [Table 4]

[0195] (Examples 4 and Comparative Example 3 in Table 4)

[0196]

[0197] It should be noted that the values in Table 4 refer to the blending amounts of the respective components, and the unit is mass%.

[0198] From Figure 5 and Figure 6 As is clearly known from the results, the amount of stratum corneum adsorbed by the preservative (ethylparaben) in Example 4 containing Polymer 1 is lower than that in Comparative Example 3 not containing the polymer of the present invention.

[0199] In other words, it can be seen that in Example 4, the percutaneous penetration of ethylparaben (logP value: 2.5), which is a preservative, is inhibited by containing Polymer 1. From this result, it is suggested that the polymer of the present invention can be used as a percutaneous penetration inhibitor for ethylparaben (logP value: 2.5), which is a preservative.

Claims

1. A composition, which is a cosmetic composition containing a polymer having a structure represented by the following formula (1) and an oily component, In the formula (1), R 1 , R 2 and R 3 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, A is an alkylene group having 2 to 4 carbon atoms, and m and n are each independently 1.0 to 50, The number-average molecular weight of the polymer is 10,000 or less, The IOB value of the polymer is 0.4 to 1.8, and The oily component is an ultraviolet absorber and / or a preservative having a logP value of 2.0 or more.

2. The composition according to claim 1, wherein in the formula (1), A is represented by the following formula (2), In the formula (2), R 4 is an alkyl group having 1 or 2 carbon atoms.

3. The composition according to claim 1 or 2, wherein the polymer is a random copolymer.

4. The composition according to claim 1 or 2, wherein in the formula (1), m is 2 or more, and at least a part of R 1 is methyl.

5. The composition according to claim 1 or 2, wherein in the formula (1), R 2 and R 3 at least one of them is methyl.

6. The composition according to claim 1 or 2, wherein the logP value of the oily component is 15.0 or less.

7. The composition according to claim 1 or 2, wherein the polymer is a percutaneous penetration inhibitor of the oily component.

8. An application, which is an application of a polymer having a structure represented by the following formula (1) as a percutaneous penetration inhibitor of an oily component, which is an ultraviolet absorber and / or a preservative having a logP value of 2.0 or more, In the formula (1), R 1 , R 2 and R 3 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, A is an alkylene group having 2 to 4 carbon atoms, and m and n are each independently 1.0 to 50, The number-average molecular weight of the polymer is 10,000 or less, and The IOB value of the polymer is 0.4 to 1.

8.

9. The application according to claim 8, wherein in the formula (1), A is represented by the following formula (2), In the formula (2), R 4 is an alkyl group having 1 or 2 carbon atoms.

10. The application according to claim 8 or 9, wherein the polymer is a random copolymer.

11. The application according to claim 8 or 9, in the formula (1), m is 2 or more, and at least a part of R 1 is methyl.

12. The application according to claim 8 or 9, wherein in the formula (1), R 2 and R 3 at least one of them is methyl.

13. The application according to claim 8 or 9, wherein the logP value of the oily component is 15.0 or less.

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