Solubilizer

A blend of polyoxyethylene polyoxypropylene alkyl ether, polyoxyethylene glyceryl fatty acid ester, and an anionic surfactant addresses transparency and stability issues in solubilizers, ensuring effective and stable solubilization of oil-soluble substances in cosmetics.

JP7855189B2Active Publication Date: 2026-05-08NIKKO CHEM
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Patent Information

Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
NIKKO CHEM
Filing Date
2022-02-02
Publication Date
2026-05-08

AI Technical Summary

Technical Problem

Existing solubilizers for oil-soluble substances in cosmetics often fail to achieve high transparency and stability over time, especially under varying temperatures, and require a significant amount of use.

Method used

A combination of polyoxyethylene polyoxypropylene alkyl ether, polyoxyethylene glyceryl fatty acid ester, and an anionic surfactant in specific ratios, along with optional polyhydric alcohol, to create a solubilizer that maintains high solubilizing ability and long-term stability.

Benefits of technology

The solubilizer achieves transparent cosmetic compositions that effectively solubilize oil-soluble substances with minimal use, maintaining stability across various temperatures and temperature cycles.

✦ Generated by Eureka AI based on patent content.

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Abstract

To provide a solubilizer that solubilizes an oil-soluble substance into an aqueous component by a smaller use amount, and can obtain a high-transparency cosmetic having excellent temporal stability.SOLUTION: To solve the above problem, an oil-soluble substance is solubilized into an aqueous component by containing the followings (A) to (C) as essential components, and thus a solubilizer that can provide a high-transparency cosmetic having excellent temporal stability is obtained. (A) polyoxyethylene polyoxypropylene alkyl ether which has a straight-chain or branched-chain alkyl group with carbon numbers of 15 to 35, in which an average addition molar number of oxyethylene group is 1 to 40 mol, and an average addition molar number of oxypropylene group is 3 to 15; (B) polyoxyethylene glyceryl fatty acid ester which has a straight-chain or branched-chain alkyl group with carbon numbers of 6 to 18, in which an average addition molar number of oxyethylene group is 3 to 20 mol; and (C) anionic surfactant.SELECTED DRAWING: None
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Description

Technical Field

[0001] The present invention relates to a solubilizer for oil-soluble substances.

Background Art

[0002] In cosmetics and makeup products, solubilizers are used to stably incorporate oil-soluble substances that do not dissolve in water into water to obtain clear cosmetics. Conventionally, in oral compositions, there has been a report of solubilizing by blending polyoxyethylene hydrogenated castor oil and polyoxyethylene polyoxypropylene alkyl ether together with an oil-soluble fragrance (Patent Document 1). Furthermore, a solubilizer has been reported that can stably maintain a solubilized state against a wide temperature range, drastic temperature changes, and light irradiation by using nonionic surfactants such as polyoxyalkylene alkyl ethers and polyoxyalkylene castor oils and anionic surfactants in a certain ratio (Patent Document 2). However, while it is common to use a solubilizer containing polyoxyalkylene castor oil, there are cases where high transparency cannot be obtained depending on the type of fragrance, and problems remain even with the above technology. Therefore, it is necessary to conduct studies to obtain better transparency.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0004] The problem of the present invention has been made in view of the problems of the above prior art, and it is to provide a solubilizer that can solubilize an oil-soluble substance in an aqueous component with a small amount of use, has excellent stability over time, and can obtain a highly transparent cosmetic. [Means for solving the problem]

[0005] As a result of diligent research by the present inventors, we have discovered that by mixing (A) a polyoxyethylene polyoxypropylene alkyl ether having a linear or branched alkyl group with 15 to 35 carbon atoms, with an average number of added moles of oxyethylene groups of 1 to 40 moles and an average number of added moles of oxypropylene groups of 3 to 15 moles, (B) a polyoxyethylene glyceryl fatty acid ester having a linear or branched alkyl group with 6 to 18 carbon atoms, with an average number of added moles of oxyethylene groups of 3 to 20 moles, and (C) an anionic surfactant in a specific ratio, we can obtain a transparent cosmetic composition that not only exhibits high solubilizing ability but also has excellent long-term stability, thus completing the present invention. [Effects of the Invention]

[0006] By using the solubilizing agent of the present invention, it is possible to provide a cosmetic composition with a transparent appearance that not only solubilizes oil-soluble substances in aqueous components with a small amount of use, but also exhibits excellent temporal stability at various temperatures, including room temperature, -5°C, 5°C, 45°C, and cycles (one cycle being -5°C → 25°C → 45°C → 25°C, with each temperature set to stand for 6 hours). [Modes for carrying out the invention]

[0007] The embodiments for carrying out the present invention will be described in more detail below. The (A) polyoxyethylene polyoxypropylene alkyl ether used in the present invention has a linear or branched alkyl group having 15 to 35 carbon atoms, and is characterized in that the average number of added moles of oxyethylene groups is 1 to 40 moles and the average number of added moles of oxypropylene groups is 3 to 15 moles. The ratio of oxyethylene groups to the total number of oxyethylene groups and oxypropylene groups is not particularly limited.

[0008] The average number of moles of oxyethylene groups added is 1 to 40, preferably 5 to 40, and more preferably 10 to 40. The average number of moles of oxypropylene groups added is 3 to 15, preferably 3 to 12, and more preferably 3 to 10. Specifically, examples include PEG-6 PPG-7 ethylhexyl ether, PPG-3 laureth-10, PPG-3 buteth-5, PPG-4 isodeceth-10, PPG-4 ceteth-1, PPG-4 ceteth-10, PPG-10 buteth-9, PPG-12 buteth-12, PPG-12 buteth-16, PPG-15 buteth-20, PPG-6 decyltetradeceth-12, PPG-6 decyltetradeceth-20, PPG-6 decyltetradeceth-30, PPG-13 decyltetradeceth-24, PPG-6 trideceth-8, PPG-8 ceteth-1, PPG-8 ceteth-10, PPG-8 ceteth-20, and others. Preferably, these are PPG-4-isodeceth-10, PPG-6-decyltetradeceth-12, PPG-6-decyltetradeceth-20, PPG-6-decyltetradeceth-30, PPG-8-ceteth-10, and PPG-8-ceteth-20.

[0009] The (A) polyoxyethylene polyoxypropylene alkyl ether in the present invention is not particularly limited depending on the intended use, but can be produced by known methods. Examples of commercially available polyoxyethylene polyoxypropylene alkyl ethers include "NIKKOL SG-DTD630" (manufactured by Nikko Chemicals Co., Ltd.), "NIKKOL PBC-44" (manufactured by Nikko Chemicals Co., Ltd.), "UNILUBE MT-0630B" (manufactured by NOF Corporation), and "UNISafe 20P-8" (manufactured by NOF Corporation).

[0010] The (B) polyoxyethylene glyceryl fatty acid ester used in the present invention is characterized by having a linear or branched alkyl group having 6 to 18 carbon atoms, and an average number of added oxyethylene groups of 3 to 20 moles. Examples of fatty acids having 6 to 18 carbon atoms that constitute the fatty acid in (B) polyoxyethylene glyceryl fatty acid ester include caproic acid, caprylic acid, capric acid, undecylic acid, undecylenic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid, among which caprylic acid, capric acid, lauric acid, myristic acid, stearic acid, and oleic acid are preferred. In addition, the fatty acids constituting the fatty acid in (B) polyoxyethylene glyceryl fatty acid ester may contain small amounts of fatty acids other than saturated or unsaturated fatty acids with 6 to 18 carbon atoms, as long as the effects targeted by the present invention are achieved. Furthermore, the average number of moles of oxyethylene groups added to (B) polyoxyethylene glyceryl fatty acid ester is 3 to 20, preferably 3 to 15, and more preferably 3 to 10.

[0011] Specifically, examples include PEG-4 (caprylic / capric acid) glyceryl, PEG-6 (caprylic / capric acid) glyceryl, PEG-6 caprate glyceryl, PEG-3 coconut oil fatty acid glyceryl, PEG-7 coconut oil fatty acid glyceryl, PEG-20 almond oil fatty acid glyceryl, PEG-20 corn oil fatty acid glyceryl, PEG-8 laurate glyceryl, PEG-12 laurate glyceryl, PEG-20 laurate glyceryl, PEG-10 oleate glyceryl, PEG-15 oleate glyceryl, PEG-20 oleate glyceryl, PEG-5 stearate glyceryl, PEG-10 stearate glyceryl, and PEG-20 stearate glyceryl. Preferably, these are PEG-6 glyceryl caprate, PEG-3 glyceryl cocoate, PEG-7 glyceryl cocoate, PEG-8 glyceryl laurate, PEG-10 glyceryl oleate, PEG-5 glyceryl stearate, and PEG-10 glyceryl stearate.

[0012] The (B) polyoxyethylene glyceryl fatty acid ester in the present invention is not particularly limited depending on the intended use, but can be produced by known methods. Examples of commercially available polyoxyethylene glyceryl fatty acid esters include "NIKKOL TMGCO-7" (manufactured by Nikko Chemicals Co., Ltd.), "M Fine Oil COG-7M" (manufactured by Miyoshi Oil & Fat Co., Ltd.), and "TEGOSOFT GC" (manufactured by Evonik Corporation).

[0013] The (C) anionic surfactant used in the present invention is an acylmethyltaurine type surfactant, and examples include caproylmethyltaurine salt, cocoylmethyltaurine salt, lauroylmethyltaurine salt, myristoylmethyltaurine salt, palmitoylmethyltaurine salt, stearoylmethyltaurine salt, and oleoylmethyltaurine salt. Preferably, it is cocoylmethyltaurine salt, lauroylmethyltaurine salt, myristoylmethyltaurine salt, or oleoylmethyltaurine salt. Examples of commercially available products include "NIKKOL CMT-30" (manufactured by Nikko Chemicals Co., Ltd.) and "NIKKOL LMT" (manufactured by Nikko Chemicals Co., Ltd.).

[0014] In the present invention, (A) polyoxyethylene polyoxypropylene alkyl ether and (B) polyoxyethylene glyceryl fatty acid ester are blended in a ratio of 1:1 to 15:1, preferably (A):(B) = 1:1 to 10:1, and more preferably (A):(B) = 1:1 to 7:1. If either (A) polyoxyethylene polyoxypropylene alkyl ether or (B) polyoxyethylene glyceryl fatty acid ester is omitted, excellent solubilization performance cannot be obtained.

[0015] The present invention is characterized by blending (A) polyoxyethylene polyoxypropylene alkyl ether and (B) polyoxyethylene glyceryl fatty acid ester with (C) an anionic surfactant in a ratio of 5:1 to 50:1, preferably (A)+(B):(C)=5:1 to 40:1, and more preferably (A)+(B):(C)=5:1 to 30:1.

[0016] The polyhydric alcohol (D) in this invention is not particularly limited, but examples include 1,3-butylene glycol, propylene glycol, dipropylene glycol, pentylene glycol, propanediol, hexanediol, octanediol, etc. Component (D) is not an essential component, but its amount in the cosmetic composition is 0.1 to 10.0%, preferably 0.1 to 5.0%. When included, it enhances the hydrophilicity of the surfactant, thereby improving solubilization performance. Furthermore, because it has solvent properties, it increases the fluidity of the solubilizer, which is advantageous in terms of improving handling during manufacturing.

[0017] The solubilizing agent of the present invention can be used to solubilize oil-soluble substances such as essential oils and fragrances commonly used in cosmetics and perfumes. The essential oil and / or fragrance may consist of only one type of oil-soluble substance as described below, or it may consist of two or more types of oil-soluble substances. Examples include peppermint oil, orange oil, lemon oil, rosemary oil, rose oil, lavender oil, heliotropin, linalool, limonene, citronellol, geraniol, vanillin, ethyl vanillin, anisyl acetate, helional, tripral, γ-undecalactone, floral ozone, cedrol, lilial, allyl amyl glycolate, terpineol, veronate, ambercore, afermate, rosephenone, narcidol, and cashmeran.

[0018] Cosmetics containing the solubilizing agent of the present invention are not particularly limited, but examples include lotions, serums, perfumes, fragrances, and hair mists.

[0019] The present invention will be described in more detail below with reference to examples, but the present invention is not limited thereto. [Examples]

[0020] 1. Method for preparing the solubilizer Solubilizers containing the components of the product of the present invention described in Tables 1 and 2 were prepared. As the preparation method, polyoxyethylene polyoxypropylene alkyl ether (A) and polyoxyethylene glyceryl fatty acid ester (B) were mixed at a ratio (weight %) of 1:1 to 15:1 in a hot water bath at 40 to 80°C. Further, an anionic surfactant (C) was mixed with the mixture of (A) and (B) at a ratio of 5:1 to 50:1, and a polyhydric alcohol (D) was added to obtain Products 1-1 to 1-6 of the present invention. As Comparative Products 1-1 to 1-5, those in which polyoxyethylene glyceryl fatty acid ester (B) was changed to polyoxyethylene hydrogenated castor oil and those without the anionic surfactant (C) were prepared.

[0021]

Table 1

[0022]

Table 2

[0023] 2. Evaluation of solubilization ability (1) Outline of the experiment Using the solubilizer of the product of the present invention, the solubilization ability for oil-soluble substances was evaluated. (2) Experimental method Using the solubilizers described in Tables 1 and 2 (Products 1-1 to 1-6 of the present invention and Comparative Products 1-1 to 1-5), and fragrance A (floral type) and fragrance B (woody floral type) of a mixed fragrance as oil-soluble substances, the following Evaluation Prescription 1 was prepared, and the solubilization ability of each solubilizer was evaluated. The evaluation method was to visually confirm the transparency according to the following evaluation criteria immediately after preparation and after storage at each temperature for 1 month at each temperature of room temperature, -5°C, 5°C, 45°C, cycle (-5°C → 25°C → 45°C → 25°C as 1 cycle, standing at each temperature for 6 hours). (3) Evaluation criteria for transparency 〇: Completely transparent △: Light transmission can be confirmed with the naked eye, but it shows a bluish color. ×: Cloudy

[0024] (4) Evaluation prescription A phase: Oil-soluble substance 1.35 (mass%) Product of the present invention / Comparative product 2.5~5.0 Dipropylene glycol 4.0 Phase B: Preservative (appropriate amount) water remainder Total 100.0 Preparation method: Mix A and B at room temperature until homogenized. Add A to B and stir to prepare the mixture.

[0025] (5) Results The evaluation results are shown in Table 3. By using the solubilizer of the present invention, it was observed that the transparency was extremely high by visual inspection, and that the stability was high at room temperature, -5°C, 5°C, 45°C, and in cycles (one cycle being -5°C → 25°C → 45°C → 25°C, with each temperature set to stand for 6 hours).

[0026] [Table 3]

[0027] The following are examples of applications of cosmetics and fragrances containing the solubilizer of the present invention. The amount is expressed in mass percent. In all of the applications 1 to 3, excellent solubilizing ability was observed using the evaluation methods of Examples 1 to 2.

[0028] Application example 1: Lotion Phase A: Squalane 0.1 (mass%) Product 1-3 of the present invention 1.0 Dipropylene glycol 5.0 Phase B: Hydroxyproline 0.2 1,3-Butylene glycol 0.3 Polyethylene glycol 4.0 Pentylene glycol 2.5 Appropriate amount of citric acid Sodium citrate (appropriate amount) Preservative (appropriate amount) Add water to reach 100.0 Preparation method: Phase A, which has been uniformly mixed at 80°C, is gradually added to Phase B while stirring with a magnetic stirrer, and stirring is continued for 30 minutes to complete the preparation. Results: The solution remained transparent both immediately after preparation and after storage.

[0029] Application Example 2: Fragrance A phase: Fragrance 1.4 (mass%) Invention 1-1 2.6 Phase B: Preservative (appropriate amount) Add water to reach 100.0 Preparation method: At room temperature, gradually add phase B to the uniformly mixed phase A while stirring with a magnetic stirrer, and continue stirring for 5 minutes to prepare the mixture. Results: The solution remained transparent both immediately after preparation and after storage.

[0030] Application Example 3: Hair Mist A phase: Essential oil 0.1 (mass%) Invention 1-6 1.0 Propanediol 5.0 Phase B: Hydrolyzed collagen 0.1 Appropriate amount of citric acid Sodium citrate (appropriate amount) Preservative (appropriate amount) Add water to reach 100.0 Preparation method: At room temperature, gradually add phase B to the uniformly mixed phase A while stirring with a magnetic stirrer, and continue stirring for 5 minutes to prepare the mixture. Results: The solution remained transparent both immediately after preparation and after storage. [Industrial applicability]

[0031] By using the solubilizer of the present invention, it is possible to provide cosmetics in which oil-soluble fragrance / essential oil components are incorporated transparently and stably.

Claims

1. A solubilizing agent containing the following components (A) to (C) as essential components, characterized in that component (A) and component (B) are blended in a ratio of 1:1 to 15:1, and component (C) is blended in a ratio of 5:1 to 50:1 with respect to the mixture of component (A) and component (B). (A) Polyoxyethylene polyoxypropylene alkyl ether having a linear or branched alkyl group having 15 to 35 carbon atoms, with an average number of added moles of oxyethylene groups of 20 to 30 moles and an average number of added moles of oxypropylene groups of 5 to 10 moles. (B) Polyoxyethylene glyceryl fatty acid ester having a linear or branched alkyl group with 6 to 18 carbon atoms and an average number of added oxyethylene groups of 3 to 20 moles. (C) Acylmethyltaurine type surfactant

2. Furthermore, the solubilizer according to claim 1, further comprising (D) a polyhydric alcohol.

Citation Information

Patent Citations

  • Silver halide photographic material containing rhodium cyanide dopant

    JP1988002042A

  • Solubilized cosmetic

    JP2001213718A

  • Oral composition

    JP2020002042A

  • Solubilization agent and use thereof, and solubilization composition

    JP2020121242A