Thickeners for cosmetics
Esterification products of 1,3-propanediol with fatty acids provide a novel solution to enhance cosmetic viscosity, effectively addressing the need for new thickeners in the cosmetics industry.
Patent Information
- Application Number
- JP2021143423
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2021-09-02
- Publication Date
- 2026-01-30
- Estimated Expiration
- 2041-09-02
AI Technical Summary
There is a constant demand for new thickeners in the cosmetics industry that can effectively increase the viscosity of cosmetic products.
The use of esterification products of 1,3-propanediol with specific fatty acids, specifically 1,3-propanediol monocaprylate, 1,3-propanediol monocaprate, and 1,3-propanediol monolaurate, as active ingredients in cosmetic thickeners.
These esters significantly increase the viscosity of cosmetics when added to cosmetic formulations, demonstrating their effectiveness as thickeners.
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Abstract
Description
[Technical Field]
[0001] The present invention relates to a thickener for cosmetics. [Background technology]
[0002] In the technical field of cosmetics, various thickeners are blended to increase the viscosity of the cosmetics. For example, organic thickeners include natural polymers such as polysaccharides, casein, and xanthan gum, and synthetic polymers such as acrylic acid polymers and carboxyvinyl polymers, while inorganic thickeners include various clay minerals such as montmorillonite and silica, and are appropriately selected and used depending on the intended effect.
[0003] Among these, thickeners with excellent thickening effects include a thickener made of a microgel obtained by dissolving a water-soluble ethylenically unsaturated monomer in a dispersed phase and radically polymerizing it in the dispersed phase (Patent Document 1) and R 1 -[(OR 2 )k-OH)] m and one or more polyether polyols represented by R 3 -(NCO) h+1 and one or more polyisocyanates represented by HO-(R 4 -O) n -R 5 has been developed (Patent Document 2), which is used in cosmetics such as hair washes.
[0004] However, in the field of cosmetics, there is a constant demand for new materials, and therefore there is also a demand for new thickeners. [Prior art documents] [Patent documents]
[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2004-43785 [Patent Document 2] Japanese Patent Application Publication No. 9-71766 Summary of the Invention [Problem to be solved by the invention]
[0006] An object of the present invention is to provide a novel thickener for cosmetics that can increase the viscosity of cosmetics. [Means for solving the problem]
[0007] As a result of intensive research into the above-mentioned problems, the present inventors have found that the above-mentioned problems can be solved by using an esterification product of 1,3-propanediol, a dihydric alcohol, with a specific fatty acid, and have completed the present invention based on this finding.
[0008] That is, the present invention comprises a thickener for cosmetics containing one or more active ingredients selected from the group consisting of 1,3-propanediol monocaprylate, 1,3-propanediol monocaprate, and 1,3-propanediol monolaurate. [Effects of the Invention]
[0009] By adding the cosmetic thickener of the present invention to a cosmetic, the viscosity of the cosmetic can be increased. DETAILED DESCRIPTION OF THE INVENTION
[0010] The cosmetic thickener of the present invention contains, as an active ingredient, one or more members selected from the group consisting of 1,3-propanediol monocaprylate, 1,3-propanediol monocaprate, and 1,3-propanediol monolaurate.
[0011] The 1,3-propanediol monocaprylate, 1,3-propanediol monocaprate, and 1,3-propanediol monolaurate used in the present invention (hereinafter also referred to as "esters of the present invention") are compounds having one ester bond, in which caprylic acid, capric acid, or lauric acid is ester-bonded to any one of the hydroxyl groups of 1,3-propanediol.
[0012] The ester of the present invention can usually be obtained by reacting 1,3-propanediol with caprylic acid, capric acid, or lauric acid (hereinafter simply referred to as "fatty acid"). For example, 1,3-propanediol and the fatty acid are heated to a temperature of 180 to 200°C and subjected to a dehydration condensation reaction for 180 to 300 minutes. The molar ratio of 1,3-propanediol to fatty acid is preferably about 1:1. A catalyst may be used to improve the reaction efficiency. Furthermore, during the reaction, it is preferable to replace the atmosphere in the reactor with an inert gas such as nitrogen to prevent discoloration of the product. The resulting reaction product is a mixture containing, in addition to the ester of the present invention, 1,3-propanediol difatty acid ester, unreacted 1,3-propanediol, fatty acid, etc. The ester of the present invention is obtained by purifying the mixture by known methods such as solvent fractionation, distillation, recrystallization, and chromatography.
[0013] The cosmetic thickener of the present invention can be used to thicken cosmetics, and is used by blending it with a cosmetic base during the production of cosmetics. The blending amount is determined appropriately depending on the target cosmetic and is not particularly limited, but from the viewpoint of usability, it is preferably 0.5 to 30 mass% relative to 100 mass% of the cosmetic, more preferably 1.0 to 20 mass%, even more preferably 3.0 to 15 mass%, and even more preferably 3.0 to 10 mass%.
[0014] Cosmetics containing the cosmetic thickener of the present invention may contain other ingredients, such as oils, preservatives, pigments, coloring matters, chelating agents, surfactants, anti-inflammatory agents, astringents, cell activators, slimming agents, whitening agents, sebum secretion inhibitors, hair removal ingredients, antioxidants, fragrances, etc., as appropriate depending on the intended use. Among these ingredients, surfactants exhibit particularly excellent thickening properties when used in combination with the cosmetic thickener of the present invention.
[0015] The surfactant may be an anionic surfactant, a cationic surfactant, an amphoteric surfactant, or a nonionic surfactant.
[0016] Examples of anionic surfactants include fatty acid salts, alkyl sulfate ester salts, polyoxyethylene alkyl sulfate salts (e.g., sodium laureth sulfate, etc.), acyl N-methyl amino acid salts, acyl amino acid salts (e.g., triethanolamine cocoyl glutamate, etc.), polyoxyethylene alkyl ether acetate salts, succinate ester salts, fatty acid alkanolamide ether carboxylate salts, acyl lactate salts, polyoxyethylene fatty amine sulfate salts, fatty acid alkanolamide sulfate salts, fatty acid glyceride sulfate salts, alkylbenzene polyoxyethylene sulfate salts, olefin sulfonates such as sodium α-olefin sulfonate, and alkyl sulfosuccinates. Examples of surfactants include alkyl phosphate ester salts such as alkyl ether sulfosuccinates, alkyl benzene sulfonates, alkyl naphthalene sulfonates, alkanesulfonates, α-sulfofatty acid methyl ester salts, acyl isethionates, alkyl glycidyl ether sulfonates, alkyl sulfoacetates, alkyl ether phosphate ester salts, and potassium lauryl phosphate; sodium caseinate; alkyl aryl ether phosphates; fatty acid amide ether phosphates; phospholipids such as phosphatidylglycerol, phosphatidylinositol, phosphatidic acid, cyclic lysophosphatidic acid, and salts thereof; and silicone-based anionic surfactants.
[0017] Examples of cationic surfactants include alkyltrimethylammonium chloride, alkyltrimethylammonium bromide, dialkyldimethylammonium chloride, fatty acid amidoamines and salts thereof, alkyletheramines and salts or quaternary salts thereof, fatty acid amide quaternary ammonium salts, polyoxyethylene alkylamines and salts or quaternary salts thereof, alkylamine salts, fatty acid amide guanidium salts, alkyletheramine ammonium salts, alkyltrialkyleneglycol ammonium salts, benzalkonium salts, benzethonium salts, pyridinium salts such as cetylpyridinium chloride, imidazolinium salts, alkylisoquinolinium salts, dialkylmorphonium salts, polyamine fatty acid derivatives, and silicone-based cationic surfactants.
[0018] Examples of amphoteric surfactants include N-alkyl-N,N-dimethyl amino acid betaines (e.g., lauryl betaine, etc.), fatty acid amidoalkyl-N,N-dimethyl amino acid betaines (e.g., cocamidopropyl betaine, etc.), imidazoline-type betaines, alkyl sulfobetaines, sulfate-type betaines, phosphate-type betaines, sphingophospholipids such as phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, and sphingomyelin, phospholipids such as lysolecithin, hydrogenated soybean phospholipid, partially hydrogenated soybean phospholipid, hydrogenated egg yolk phospholipid, partially hydrogenated egg yolk phospholipid, and hydroxylated lecithin, and silicone-based amphoteric surfactants.
[0019] Examples of nonionic surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, castor oil and hydrogenated castor oil derivatives, polyoxyethylene phytosterol, polyoxyethylene cholesterol, polyoxyethylene cholestanol, polyoxyethylene lanolin, polyoxyethylene reduced lanolin, polyoxyethylene-polyoxypropylene alkyl ethers, polyoxyethylene-polyoxypropylene glycol, (poly)glycerin polyoxypropylene glycol, glycerin fatty acid partial esters, polyglycerin fatty acid esters, ethylene glycol mono fatty acid esters, propylene glycol mono fatty acid esters, pentaerythritol partial fatty acid esters, sorbitol partial fatty acid esters, maltitol partial fatty acid esters, maltitol ethers, sorbitan fatty acid esters, sugar derivative partial esters, alkyl glucosides, alkyl polyglycosides, glycolipids, Examples of surfactants include lanolin alcohol, reduced lanolin, polyoxyethylene fatty acid mono- and diesters, polyoxyethylene-propylene glycol fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, polyoxyethylene methyl glucoside fatty acid esters, polyoxyethylene alkyl ether fatty acid esters, polyoxyethylene animal and vegetable oils and fats, alkyl glyceryl ethers, polyhydric alcohol alkyl ethers, polyoxyethylene alkylamines, tetrapolyoxyethylene-tetrapolyoxypropylene-ethylenediamine condensates, saponin, natural surfactants such as sophorolipids, polyoxyethylene fatty acid amides, fatty acid alkanolamides, alkyldimethylamine oxides, alkylethoxydimethylamine oxides, polyoxyethylene alkyl mercaptans, and silicone-based nonionic surfactants.
[0020] When a surfactant is blended into a cosmetic containing the cosmetic thickener of the present invention, the amount of surfactant blended is determined appropriately depending on the target cosmetic and is not particularly limited, but from the viewpoints of cleansing properties, usability, and blending costs, the amount is preferably 10 to 80 mass%, and more preferably 30 to 75 mass%, relative to 100 mass% of the cosmetic.
[0021] Examples of cosmetics that can be blended with the cosmetic thickener of the present invention include packs, massage products, shaving products, depilatories, facial cleansers, hair treatments, and hair washes, with hair washes being particularly preferred.
[0022] The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples. [Example]
[0023] [Manufacturing Example 1] [Preparation of 1,3-propanediol monocaprylate (Example 1)] A 1000 mL four-neck glass flask equipped with a mercury thermometer, nitrogen inlet tube, reflux condenser, and stirrer was charged with 404.48 g of caprylic acid (trade name: PALMAC 99-08; IOI Acidchem Co., Ltd.) and 395.52 g of 1,3-propanediol (Fujifilm Wako Pure Chemical Industries, Ltd.), and 0.28 g of stannous oxide (Fujifilm Wako Pure Chemical Industries, Ltd.) as a catalyst. Nitrogen was introduced at 200 mL / min, and the mixture was heated to 200 °C with stirring. The reaction was continued at this temperature for 4 hours. After completion of the reaction, the mixture was cooled to 110 °C and neutralized with 0.14 g of 85% aqueous phosphoric acid solution (Fujifilm Wako Pure Chemical Industries, Ltd.). The reflux condenser was connected to a Claisen tube, Liebig condenser, and distillate receiver, and the resulting reaction mixture was distilled under reduced pressure at 3 kPa. The fraction with a distillation temperature of 150°C to 156°C was designated as 1,3-propanediol monocaprylate (Example 1).
[0024] [Manufacturing Example 2] [Production of 1,3-propanediol monocaprate (Example 2)] The reaction and reduced pressure distillation were carried out in the same manner as in Production Example 1, except that 404.48 g of caprylic acid in Production Example 1 was replaced with 440.64 g of capric acid (trade name: NAA-102; manufactured by NOF Corporation) and the amount of 1,3-propanediol charged in Production Example 1 was changed to 359.36 g. The fraction with a distillation temperature of 115°C to 166°C was designated 1,3-propanediol monocaprate (Example 2).
[0025] [Manufacturing Example 3] [Production of 1,3-propanediol monolaurate (Example 3)] Reaction and vacuum distillation were carried out in the same manner as in Production Example 1, except that 404.48 g of caprylic acid in Production Example 1 was replaced with 469.52 g of lauric acid (trade name: NAA-122; manufactured by NOF Corporation) and the amount of 1,3-propanediol charged in Production Example 1 was changed to 330.48 g. The fraction distilled at distillation temperatures from 83°C to 181°C was designated 1,3-propanediol monolaurate (Example 3).
[0026] [Manufacturing Example 4] [Production of 1,3-propanediol monomyristate (Comparative Example 1)] The reaction and reduced pressure distillation were carried out in the same manner as in Production Example 1, except that the 404.48 g of caprylic acid in Production Example 1 was replaced with 494.8 g of myristic acid (trade name: EDENOR C14-99(c); manufactured by EMERY OLEOCHEMICALS) and the amount of 1,3-propanediol charged was changed to 305.2 g. The fraction distilled at a temperature between 143°C and 205°C was designated as 1,3-propanediol monomyristate (Comparative Example 1).
[0027] [Manufacturing Example 5] [Production of 1,3-propanediol monostearate (Comparative Example 2)] Reaction and vacuum distillation were carried out in the same manner as in Production Example 1, except that 404.48 g of caprylic acid in Production Example 1 was replaced with 534.8 g of stearic acid (trade name: Lunac S-98; manufactured by Kao Corporation) and the amount of 1,3-propanediol charged was changed to 265.2 g. The fraction distilled at a distillation temperature of 150°C to 230°C was designated as 1,3-propanediol monostearate (Comparative Example 2).
[0028] Table 1 shows the carbon numbers of the constituent fatty acids for each of the esters obtained in Production Examples 1 to 5 (Examples 1 to 3 and Comparative Examples 1 and 2).
[0029] [Table 1]
[0030] [Test Example 1] [Preparation and Evaluation of Hair Wash Using Sodium Laureth Sulfate] (1) Ingredients of hair wash 1) Sodium laureth sulfate (trade name: Taipol NLES-327; manufactured by Taiko Yushi Kagaku Kogyo Co., Ltd.) 2) 1,3-Propanediol Monocaprylate (Example 1) 3) 1,3-Propanediol Monocaprate (Example 2) 4) 1,3-Propanediol Monolaurate (Example 3) 5) 1,3-Propanediol Monomyristate (Comparative Example 1) 6) 1,3-Propanediol Monostearate (Comparative Example 2) 7) Purified water
[0031] Table 2 shows the formulations of hair washes 1 to 6 prepared using the above raw materials.
[0032] [Table 2]
[0033] (2) Preparation of hair wash Sodium laureth sulfate, each ester as a thickener, and distilled water were placed in a 300 mL glass beaker according to Table 2, and the mixture was stirred with a stirring blade in a water bath at 80°C for 30 minutes. The mixture was cooled to room temperature while continuing to stir, and hair washes 1 to 6 (100 g each) were prepared.
[0034] (3) Viscosity measurement The viscosity (mPa·S) of hair washes 1 to 6 was measured at 20°C using a Brookfield viscometer (model: TVB10; manufactured by Toki Sangyo Co., Ltd.). For the measurement, a spindle-type rotor M4 was attached to the viscometer, and the value was read after rotating at a rotation speed of 12 rpm for 1 minute. The results are shown in Table 3.
[0035] [Table 3]
[0036] As is clear from the results in Table 3, hair washes 1 to 3 containing the esters of Examples 1 to 3 of the present invention had significantly higher viscosities than hair wash 6, which did not contain a thickener, confirming that the esters of the present invention are useful as thickeners. However, hair washes 4 and 5 containing the esters of Comparative Examples 1 and 2 of the present invention did not provide a sufficient thickening effect and were inferior to those containing the esters of the present invention.
[0037] [Test Example 2] [Preparation and Evaluation of Hair Washes Using Surfactants Other than Sodium Laureth Sulfate]
[0038] (1) Ingredients of hair wash 1) Lauryl betaine (trade name: Obazoline LB-SF; manufactured by Toho Chemical Industry Co., Ltd.) 2) Cocamidopropyl betaine (product name: Rikabion B-200; manufactured by New Japan Chemical Co., Ltd.) 3) Triethanolamine cocoyl glutamate (trade name: AminoSurfact ACMT-L; manufactured by Asahi Kasei Finechem Co., Ltd.) 4) 1,3-Propanediol Monolaurate (Example 3) 5) Purified water
[0039] Table 4 shows the formulations of hair washes 7 to 12 prepared using the above raw materials.
[0040] [Table 4]
[0041] (2) Preparation of hair wash A 300 mL glass beaker was charged with surfactant, thickener, and distilled water according to Table 4, and the mixture was stirred with a stirring blade in a water bath at 80°C for 30 minutes. The mixture was cooled to room temperature while continuing to stir, and hair washes 7 to 12 (100 g each) were prepared.
[0042] (3) Viscosity measurement The viscosity (mPa·S) of hair washes 7 to 12 was measured at 20°C using a Brookfield viscometer (model: TVB10; manufactured by Toki Sangyo Co., Ltd.). For the measurement, a spindle-type rotor M4 was attached to the viscometer, and the value was read after rotating at a rotation speed of 12 rpm for 1 minute. The results are shown in Table 5.
[0043] [Table 5]
[0044] As is clear from the results in Table 5, in all of hair washes 7 and 8, which used lauryl betaine as a surfactant, hair washes 9 and 10, which used cocamidopropyl betaine, and hair washes 11 and 12, which used lauryl betaine and triethanolamine cocoyl glutamate, the viscosity of the hair wash increased when the amount of thickener added was increased from 4.0% by mass to 6.0% by mass. Therefore, it was confirmed that the ester of the present invention is also useful as a thickener for hair washes that use surfactants other than sodium laureth sulfate.
Claims
1. A thickener for cosmetics containing one or more active ingredients selected from the group consisting of 1,3-propanediol monocaprate and 1,3-propanediol monolaurate, and containing an anionic surfactant and / or an amphoteric surfactant.
2. A thickener for cosmetics as described in claim 1, wherein the amount of anionic surfactant and amphoteric surfactant blended relative to 100% by mass of the cosmetic is 10 to 80% by mass.
Citation Information
Patent Citations
Viscosity modifier
JP1997071766A
Thickener and cosmetic obtained by formulating the same
JP2004043785A
Composition containing monoester and diester of 1,3-propanediol in biological basis
JP2014055138A
Active agents for skin and hair care with physicochemical modifying properties
WO2020160904A1