Oil-gelling agent, and oil gel using the same

Abstract

To provide an oil-gelling agent which can obtain oil gel that is excellent in shape retention and color development property of a coloring agent, can maintain shape retention and color development property even after having been exposed to a high temperature and high humidity condition, and prevents generation of oil staining.SOLUTION: An oil-gelling agent contains dialkyl ketone A having 29 to 61 carbon atoms and an average carbon number represented by a, and dialkyl ketone B having 21 to 55 carbon atoms and an average carbon number represented by b, wherein a difference (a-b) between the a and the b is 2 or more and 8 or less, and a mass ratio of the dialkyl ketone A to the dialkyl ketone B is 70:30 to 99.9:0.1.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to an oil gelling agent and an oil gel using the same.

Background Art

[0002] An oil gel is a gelled product of a liquid oil agent at room temperature using a wax which is a solid oil agent at room temperature, and is used in fields such as cosmetics, quasi-drugs, and daily sundries. Since the sliding part collapses when the surface is rubbed and can be applied to an object, the oil gel is widely used as a base for lipsticks, foundations, crayons, and cream pastels.

[0003] As the wax used for the oil gel, paraffin wax, polyethylene, olefin copolymer, etc. are widely used. However, against the backdrop of the increasing environmental awareness in recent years, the need for natural-derived raw materials has been growing. Examples of natural-derived waxes include carnauba wax and candelilla wax. On the other hand, when these waxes are used as a gelling agent, depending on the type of oil, the gelling ability may be insufficient and the shape and hardness may not be retained, or the high molecular weight components (resins) derived from the wax may settle and the appearance may become non-uniform. In contrast, Patent Document 1 discloses a wax composition containing a fatty acid ester and beeswax as active ingredients as a novel oil gelling agent using natural-derived raw materials.

[0004] The wax in the oil gelling agent (wax composition) does not necessarily need to exhibit gelling performance only when compounded into the oil gel. For products such as lip creams, it is necessary to maintain the gelled state over a long period. In the oil gel, the wax forms a crystal structure called a card house structure, and the oil penetrates into this structure to maintain the gelled state. However, when the strength of the crystal is low, the crystal structure may collapse due to the application of energy such as load, vibration, and heat, which can cause shape collapse and oiliness inside the storage packaging. Also, in lipsticks, crayons, etc., there is concern about a decrease in the color development property of the colorant due to the above problems. To address such issues, Patent Document 2 discloses a wax composition in which candelilla wax and monoester wax are blended at a specific mass ratio as an oil gelling agent capable of imparting shape stability. Further, Patent Document 3 discloses an oily solid cosmetic in which a solid oil having a specific melting point and a fatty acid ester are used in combination to improve the color development property of the colorant.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

Patent Document 3

Summary of the Invention

Problems to be Solved by the Invention

[0006] Thus, various improvement measures have been disclosed for the problems of oil gels. However, since lipsticks, crayons, etc. are used in daily life, they are often exposed to the external environment from the rainy season to summer, which is hot and humid. Furthermore, in the case of lipsticks, from winter to early spring when the opportunity to wear masks increases for preventing influenza, colds, or hay fever, they are exposed to the high-humidity environment inside the masks. Against this background, there is a demand for an oil gelling agent that can realize an oil gel with less oil stain, easy shape retention, and excellent temporal stability of the color development property of the colorant even under high-temperature and high-humidity environments. However, none of the above-mentioned documents have examined the performance of oil gels assuming a high-temperature and high-humidity environment and their temporal stability, and there was a possibility that the desired performance was not satisfied.

[0007] The present invention has been made in view of the above problems, and an object thereof is to provide an oil gel that is excellent in shape retention and color development property of a colorant, can maintain shape retention and color development property even after being exposed to high-temperature and high-humidity conditions, and is less likely to cause oil stain, and an oil gelling agent capable of realizing the same.

Means for Solving the Problems

[0008] As a result of intensive studies to solve the above problems, the present inventors have found that an oil gel using an oil gelling agent containing specific two types of dialkyl ketones is excellent in shape retention and color development property of a colorant, can maintain shape retention and color development property even after being exposed to high-temperature and high-humidity conditions, and is also less likely to cause oil stain, and thus have completed the present invention.

[0009] That is, the present invention provides an oil gelling agent containing a dialkyl ketone A having 29 to 61 carbon atoms and an average carbon number of a and a dialkyl ketone B having 21 to 55 carbon atoms and an average carbon number of b, wherein the difference (a - b) between a and b is 2 or more and 8 or less, and the mass ratio of the dialkyl ketone A to the dialkyl ketone B is 70:30 to 99.9:0.1.

[0010] The present invention also provides an oil gel containing the above oil gelling agent and oil, and containing 0.1 to 30 parts by mass of the oil gelling agent with respect to 100 parts by mass of the oil.

Advantages of the Invention

[0011] The oil gel using the oil gelling agent of the present invention is excellent in shape retention and color development property of a colorant. Further, the oil gel can maintain the shape retention and color development property even after being exposed to high temperature and high humidity conditions, and can also suppress oil stain.

Modes for Carrying Out the Invention

[0012] Hereinafter, embodiments of the present invention will be described. In this specification, a numerical range defined using the symbol "~" includes the numerical values at both ends (upper limit and lower limit) of "~". For example, "2~10" represents a range of 2 or more and 10 or less.

[0013] 1. Oil gelling agent The oil gelling agent of the present invention contains at least two kinds of dialkyl ketones, namely dialkyl ketone A and dialkyl ketone B. Dialkyl ketone A is a dialkyl ketone having 29 to 61 carbon atoms and an average carbon number of a, and dialkyl ketone B is a dialkyl ketone having 21 to 55 carbon atoms and an average carbon number of b. Dialkyl ketones generally may have a molecular weight distribution when analyzed by gel permeation chromatography (GPC). Therefore, in this specification, the "carbon number" of dialkyl ketone means the distribution of the number of carbons when each dialkyl ketone is analyzed by gel permeation chromatography (GPC). Further, having 29 to 61 carbon atoms means that the carbon number (distribution of the number of carbons) is within this range, and does not mean that the distribution of the number of carbons necessarily spreads from 29 to 61. Also, in this specification, the "average carbon number" refers to the carbon number of the peak in the distribution of the number of carbons observed when the dialkyl ketone is measured by GPC.

[0014] Incidentally, the oil gelling agent of the present invention may contain three or more kinds of dialkyl ketones. In this specification, among the dialkyl ketones contained in the oil gelling agent, the dialkyl ketone having 29 to 61 carbon atoms and the highest content is treated as dialkyl ketone A. On the other hand, among the dialkyl ketones contained in the oil gelling agent, a compound having an average carbon number (b) that is 2 to 8 less than the average carbon number a of dialkyl ketone A and having 21 to 55 carbon atoms is treated as dialkyl ketone B. Note that the oil gelling agent only needs to contain at least one compound corresponding to dialkyl ketone B, and may contain two or more kinds. Furthermore, the oil gelling agent may further contain a dialkyl ketone having 21 to 61 carbon atoms that does not correspond to the above-mentioned dialkyl ketone A and dialkyl ketone B (hereinafter also referred to as "other dialkyl ketones") as long as the object and effect of the present invention are not impaired.

[0015] In addition, the oil gelling agent of the present invention may contain components other than dialkyl ketones, and may contain, for example, fatty acid amide C and β-ketocarboxylic acid D described later. Hereinafter, each component will be described.

[0016] 〔Dialkyl ketone A〕 The dialkyl ketone A used in the present invention is a compound containing one carbonyl group and having aliphatic chains (alkyl groups) bonded to both sides thereof, and any compound having 29 to 61 carbon atoms may be used. The average carbon number a of the dialkyl ketone A is 29 or more and 61 or less. The dialkyl ketone A may be composed of a single component, or may be a mixture having a certain molecular weight distribution as described above. The carbon number and the average carbon number a of the dialkyl ketone A only need to be 29 to 61, preferably 29 to 51, and more preferably 29 to 41.

[0017] Here, the two aliphatic chains in the dialkyl ketone A may be the same or different. However, from the perspective of the crystallinity of the dialkyl ketone A, the difference in the number of carbon atoms between the two aliphatic chains is preferably 2 or less, more preferably 0. Each aliphatic chain may be linear or branched, but a linear chain is preferred. Also, each aliphatic chain may be either saturated or unsaturated, but being saturated is preferred.

[0018] Examples of the ketone used for the dialkyl ketone A include dipentadecyl ketone, dihexadecyl ketone, diheptadecyl ketone, heptadecyl pentadecyl ketone, dioctadecyl ketone, dinonadecyl ketone, dieicosyl ketone, diheneicosyl ketone, didocosyl ketone, ditricosyl ketone, ditetracosyl ketone, dioctacosyl ketone, didecacosyl ketone, and the like.

[0019] The method for preparing the above dialkyl ketone A is not particularly limited. For example, in the presence of a metal oxide catalyst, a carboxylic acid having a desired aliphatic chain is reacted at a high temperature (preferably at a temperature of 300 to 350 °C) and under high pressure (preferably 0.1 to 5 MPa), and can be obtained by decarboxylation. Examples of the metal oxide catalyst that can be used include magnesium oxide, calcium oxide, zinc oxide, and the like. The carboxylic acid is appropriately selected according to the desired number of carbon atoms, and examples thereof include palmitic acid, margaric acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, and the like.

[0020] On the other hand, when preparing the above dialkyl ketone A, instead of the above carboxylic acid and metal oxide catalyst, a metal carboxylate such as magnesium carboxylate, calcium carboxylate, zinc carboxylate, etc. may be used. Representative examples thereof include magnesium stearate, calcium stearate, zinc stearate, magnesium behenate, calcium behenate, zinc behenate, magnesium palmitate, magnesium montanate, magnesium eicosanoate, magnesium hexacosanoate, magnesium heptadecanoate, and the like.

[0021] [Dialkyl ketone B] The dialkyl ketone B used in the present invention is a compound containing one carbonyl group and having aliphatic chains bonded to both sides thereof, and the number of carbon atoms thereof is 21 to 55. Further, the average number of carbon atoms b thereof is 21 or more and 55 or less, and the difference (a - b) between the average number of carbon atoms b and the average number of carbon atoms a of the above-mentioned dialkyl ketone A may be 2 or more and 8 or less. The dialkyl ketone B may be composed of a single component, or may be a mixture having a certain molecular weight distribution as described above. The number of carbon atoms and the average number of carbon atoms b of the dialkyl ketone B may be 21 to 55, preferably 25 to 41, and more preferably 31 to 41. As described above, the oil gelling agent may contain only one kind of compound corresponding to the dialkyl ketone B, or may contain two or more kinds.

[0022] The difference (a - b) between the average number of carbon atoms a of the above-mentioned dialkyl ketone A and the average number of carbon atoms b of the above-mentioned dialkyl ketone B may be 2 or more and 8 or less, preferably 2 or more and 6 or less. When the difference between the average number of carbon atoms a of the dialkyl ketone A and the average number of carbon atoms b of the above-mentioned dialkyl ketone B is within the above range, the crystallinity of the dialkyl ketone A can be appropriately reduced by the dialkyl ketone B.

[0023] Here, the two aliphatic chains in the dialkyl ketone B may be the same or different. However, the difference in the number of carbon atoms of the two aliphatic chains is preferably 2 or less, more preferably 0. Each aliphatic chain may be linear or branched, but a linear chain is preferred. Further, each aliphatic chain may be either saturated or unsaturated, but a saturated one is preferred.

[0024] Examples of the dialkyl ketone used for the dialkyl ketone B include didecyl ketone, diundecyl ketone, didodecyl ketone, ditridecyl ketone, ditetradecyl ketone, dipentadecyl ketone, dihexadecyl ketone, diheptadecyl ketone, heptadecyl pentadecyl ketone, dioctadecyl ketone, dinonadecyl ketone, dieicosyl ketone, diheneicosyl ketone, didocosyl ketone, ditricosyl ketone, ditetracosyl ketone, dihexacosyl ketone, dioctacosyl ketone, and the like.

[0025] The method for preparing the dialkyl ketone B is not particularly limited, and it can be the same as the method for preparing the above dialkyl ketone A.

[0026] [Content of dialkyl ketone A and dialkyl ketone B] The mass ratio of the dialkyl ketone A to the dialkyl ketone B in the oil gelling agent may be 70:30 to 99.9:0.1, and 80:20 to 99.9:0.1 is more preferable. When two or more compounds corresponding to the dialkyl ketone B are included, it is preferable that the ratio of the content of the dialkyl ketone A to the total amount of the compounds corresponding to the dialkyl ketone B falls within the above range. When the oil gelling agent contains the above dialkyl ketone A and dialkyl ketone B in such a mass ratio, the crystal acceleration rate of the oil gelling agent is easily controlled, and local crystallization is suppressed. As a result, when made into an oil gel, oil can be uniformly retained in the crystals of the oil gelling agent, and shape retention and oiliness can be suppressed. Furthermore, since the colorant is uniformly dispersed, it is considered that the color development property is improved.

[0027] As described above, the oil gelling agent of the present invention may further contain other dialkyl ketones other than the dialkyl ketone A and the dialkyl ketone B as described above. The total amount of the other dialkyl ketones is preferably 5% by mass or less, more preferably 2% by mass or less, based on the total amount of the dialkyl ketone A and the dialkyl ketone B.

[0028] [Fatty acid amide C] As described above, the oil gelling agent of the present invention may further contain a fatty acid amide C composed of a tertiary amide compound obtained from a monovalent monocarboxylic acid and a dialkylamine. By using the fatty acid amide C in combination with the above-mentioned dialkyl ketone A and dialkyl ketone B, when used in an oil gel, not only can the color development property of the colorant contained in the oil gel be further enhanced, but also the color development property and shape retention property are more likely to be maintained even after being left in a high-temperature and high-humidity environment. In addition, oil stain after being left in a high-temperature and high-humidity environment can also be suppressed.

[0029] The number of carbon atoms of the monovalent monocarboxylic acid used for synthesizing the fatty acid amide C is preferably 16 to 24, more preferably 16 to 22. Examples of the monovalent monocarboxylic acid include stearic acid, arachidic acid, behenic acid, palmitic acid, etc. The dialkylamine used for synthesizing the fatty acid amide C may be an amine having two alkyl groups, and the two alkyl groups may be the same or different. Each of these alkyl groups preferably has 1 to 3 carbon atoms. Examples of the dialkylamine include dimethylamine, diethylamine, dipropylamine, etc.

[0030] Specific examples of the fatty acid diamide C include N,N-diethyl stearic acid amide, N,N-dipropyl stearic acid amide, N,N-diethyl behenic acid amide, N,N-dipropyl behenic acid amide, N,N-diethyl palmitic acid amide, N,N-dipropyl palmitic acid amide, etc.

[0031] In addition, the amount of the fatty acid amide C in the oil gelling agent is preferably 0.1 to 5% by mass based on the total amount of the dialkyl ketone having 21 to 61 carbon atoms (particularly, the total amount of the dialkyl ketone A and dialkyl ketone B).

[0032] The production method of the above-mentioned fatty acid amide C is not particularly limited, but for example, it can be obtained by dehydrative condensation of the aforementioned monovalent monocarboxylic acid and dialkylamine under the conditions of 80 to 250 °C.

[0033] [[β-Ketocarboxylic acid D]] As described above, it is preferable that the oil gelling agent of the present invention contains β-ketocarboxylic acid D represented by the following general formula (I). By using the above dialkyl ketone A and the above dialkyl ketone B in combination with β-ketocarboxylic acid D, the color developability of the colorant in the oil gel becomes even better. Further, even after standing at high temperature and high humidity, it becomes easier to maintain the color developability and shape retention, and oil bleeding can also be suppressed. Further, by using fatty acid amide C and β-ketocarboxylic acid D in combination with dialkyl ketone A and dialkyl ketone B, the color developability of the colorant becomes even better, and the color developability and shape retention are easily maintained even after standing at high temperature and high humidity, and oil staining is less likely to occur. [[Chemical formula]] In the above general formula (I), R 1 and R 2 each independently represent a linear saturated alkyl group having 14 to 22 carbon atoms.

[0034] From the viewpoint of suppressing bleeding from the oil gel, the β-ketocarboxylic acid compound represented by the above general formula (I) is preferably solid at room temperature, more preferably having a clear melting point of 40°C or higher. Further, from the same viewpoint, R 1 and R 2 in the structure are each independently preferably a linear saturated alkyl group having 14 to 22 carbon atoms, and more preferably a linear saturated alkyl group having 16 to 22 carbon atoms.

[0035] Specific examples of β-ketocarboxylic acid D include 2-hexadecyl-3-oxoeicosanoic acid, 2-tetradecyl-3-oxooctadecanoic acid, 2-icosyl-3-oxotetracosanoic acid, and the like.

[0036] The amount of β-ketocarboxylic acid D in the oil gelling agent of the present invention is preferably 0.01 to 2% by mass based on the total amount of the dialkyl ketone having 21 to 61 carbon atoms (particularly, the total amount of dialkyl ketone A and dialkyl ketone B).

[0037] The method for synthesizing the β-ketocarboxylic acid represented by the above general formula (I) is not particularly limited, and known methods or methods analogous thereto can be used. For example, it can be obtained by dimerizing a fatty acid chloride in an organic base and then hydrolyzing it. At this time, the organic base is not particularly limited, but in order to obtain the target product in good yield, it is preferable to use a tertiary amine compound from the reactivity with the fatty acid chloride. Examples of the tertiary amine compound include triethylamine, triisopropylamine, triphenylamine, and the like. Among these, it is preferable to use triethylamine from the viewpoint of easy separation from the product.

[0038] Also, it is preferable to use a basic aqueous solution for hydrolysis, and in order to suppress the excessive formation of the neutralization salt with the generated β-ketocarboxylic acid compound, the amount of the base is preferably 1 mol% or less, more preferably 0.5 mol% or less, based on the theoretical amount of the β-ketocarboxylic acid compound to be generated. There is no particular specification for the base to be used, and examples include potassium hydroxide, sodium hydroxide, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, and the like.

[0039] 〔Method for Preparing Oil Gelling Agent〕 To obtain the oil gelling agent of the present invention, the above-described dialkyl ketone A and dialkyl ketone B, and other components such as fatty acid amide C and β-ketocarboxylic acid D, if necessary, may be individually synthesized and then mixed. On the other hand, for those that can be synthesized in one batch, they may be synthesized in one batch. When mixing the individually synthesized components, it is preferable to heat and dissolve them at a temperature equal to or higher than the melting point of each component and mix them uniformly, and then cool and solidify them and pulverize or granulate them to produce the oil gelling agent of the present invention.

[0040] 2. Oil Gel The oil gel of the present invention only needs to contain an oil and the above-described oil gelling agent, and may contain a colorant if necessary. The oil gel is produced by a usual production method.

[0041] The above oil gel may contain other waxes as required. Examples of other waxes include petroleum waxes such as paraffin wax and microcrystalline wax, and natural waxes such as carnauba wax, candelilla wax, ozokerite, and ceresin, etc. Those with a melting point of 50 °C or higher at normal pressure can be mentioned, but it is not limited to these.

[0042] Examples of the oil include hydrocarbon oils, branched fatty acids, branched alcohols, ester oils, ether oils, and the like. Specifically, examples of the hydrocarbon oil include squalane, squalene, liquid paraffin, α-olefin oligomer, hydrogenated polyisobutene, isoparaffin, and the like. Examples of the branched fatty acid include 2-ethylhexanoic acid, isononanoic acid, isopalmitic acid, isostearic acid, isobehenic acid, and the like. Examples of the branched alcohol include isostearyl alcohol, octyldodecanol, hexyldecanol, decyltetradecanol, oleyl alcohol, and the like. Examples of the ester oil include 2-ethylhexyl 2-ethylhexanoate, isononyl 2-ethylhexanoate, diisobutyl adipate, di-2-ethylhexyl succinate, cetyl 2-ethylhexanoate, 2-hexyldecyl 2-ethylhexanoate, neopentyl glycol di-2-ethylhexanoate, trimethylolpropane tri-2-ethylhexanoate, medium-chain fatty acid triglyceride, neopentyl glycol dicaprate, 2-ethylhexyl isononanoate, isononyl isononanoate, isodecyl isononanoate, isotridecyl isononanoate, hexyl laurate, isopropyl myristate, 2-hexyldecyl myristate, 2-octyldodecyl myristate, isopropyl palmitate, 2-ethylhexyl palmitate, 2-hexyldecyl stearate, ethyl isostearate, isopropyl isostearate, 2-hexyldecyl isostearate, isostearyl isostearate, isodecyl neopentanoate, isostearyl neopentanoate, octyldodecyl neopentanoate, 2-octyldodecyl dimethyloctanoate, 2-ethylhexyl hydroxystearate, 2-octyldodecyl 12-stearoylstearate, oleyl oleate, 2-ethylhexyl salicylate, dialkyl carbonate, and the like. Examples of the ether oil include dioctyl ether, polyoxyethylene·polyoxypropylene dimethyl ether, and the like. Among these, hydrocarbon oils and ester oils are preferred, and hydrogenated polyisobutene is preferred as the hydrocarbon oil, and cetyl 2-ethylhexanoate is preferred as the ester oil.

[0043] The oil gel of the present invention contains an oil and the above-mentioned oil gelling agent, and the amount of the oil gelling agent is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the oil. The above-mentioned oil gelling agent is contained in the oil gel alone or in combination of two or more kinds.

[0044] The oil gel of the present invention may contain a colorant as needed. The colorant is not particularly limited, and examples thereof include conventionally known ones such as colored pigments, pearl pigments, and tar dyes.

[0045] Specific examples of the colored pigment include inorganic red pigments such as iron oxide, iron hydroxide, and iron titanate; inorganic brown pigments such as γ-iron oxide; inorganic yellow pigments such as yellow iron oxide and loess; inorganic black pigments such as black iron oxide and carbon black (INCI); inorganic purple pigments such as manganese violet (INCI: Manganese Violet) and cobalt violet; inorganic green pigments such as chromium hydroxide (INCI: Chromium Hydroxide Green), chromium oxide (INCI: Chromium Oxide Greens), cobalt oxide, and cobalt titanate (INCI: Cobalt Titanium Oxide); inorganic blue pigments such as ultramarine and cerulean blue; lake pigments of tar dyes, lake pigments of natural pigments, and synthetic resin powders obtained by compounding these powders; and the like.

[0046] Specific examples of the pearl pigment include mica coated with titanium oxide, mica coated with titanium oxide, bismuth oxychloride, bismuth oxychloride coated with titanium oxide, talc coated with titanium oxide, fish scale foil, and colored mica coated with titanium oxide. Examples of the metal powder pigment include aluminum powder, copper powder, and stainless steel powder.

[0047] Examples of tar dyes include Red No. 3, Red No. 104, Red No. 106, Red No. 201, Red No. 202, Red No. 204, Red No. 205, Red No. 215, Red No. 220, Red No. 226, Red No. 227, Red No. 228, Red No. 230, Red No. 401, Red No. 505, Yellow No. 4, Yellow No. 5, Yellow No. 202, Yellow No. 203, Yellow No. 204, Yellow No. 401, Blue No. 1, Blue No. 2, Blue No. 201, Blue No. 404, Green No. 3, Green No. 201, Green No. 204, Green No. 205, Orange No. 201, Orange No. 203, Orange No. 204, Orange No. 206, Orange No. 207, etc.; examples of natural dyes include powders selected from carminic acid, laccaic acid (INCI: Laccaic Acid), carthamin, brazilein, crocin, etc.

[0048] The amount of the colorant is appropriately selected according to the use, but is preferably 0.05 to 30 parts by mass with respect to 100 parts by mass of the oil.

Examples

[0049] Hereinafter, the present invention will be described more specifically with reference to Examples and Comparative Examples.

[0050] 1. Preparation of oil gelling agent (1) Preparation of dialkyl ketone A Four types of dialkyl ketone A were prepared by the following method.

[0051] [Production Example A1: Preparation of dialkyl ketone A1] In a 1 L separable flask made of SUS, 700.0 g of magnesium stearate (product name: Nissan Electol MM-2, manufactured by NOF Corporation, stearic acid content: 98% by mass) was weighed, and the temperature was raised to 250 °C while blowing nitrogen. At this time, the moisture contained in the material was distilled out of the system. Then, nitrogen was pressured in at 2 MPa, the temperature was raised to 340 - 350 °C, and after continuing the reaction for 8 hours, it was cooled to 100 °C to obtain a crude dialkyl ketone compound. While blowing nitrogen, at 100 °C, using a 100-mesh metal strainer, the obtained crude dialkyl ketone compound was filtered to remove magnesium oxide produced as a by-product, thereby obtaining dialkyl ketone A1 (diheptadecyl ketone).

[0052] [Production Example A2: Preparation of Dialkyl Ketone A2] Dialkyl ketone A2 (diheneicosyl ketone) was obtained in the same manner as dialkyl ketone A1, except that magnesium behenate was used as the main raw material.

[0053] [Production Example A3: Preparation of Dialkyl Ketone A3] Dialkyl ketone A3 (dipentadecyl ketone) was obtained in the same manner as dialkyl ketone A1, except that magnesium palmitate was used as the main raw material.

[0054] [Production Example A4: Preparation of Dialkyl Ketone A4] Dialkyl ketone A4 (dioctacosyl ketone) was obtained in the same manner as dialkyl ketone A1, except that magnesium montanate was used as the main raw material.

[0055] [Summary of Dialkyl Ketone A] The carbon number and average carbon number a of each dialkyl ketone A prepared above are shown below.

Table 1

[0056] (2) Preparation of Dialkyl Ketone B Five types of dialkyl ketone B were prepared by the following method.

[0057] [Production Example B1: Preparation of Dialkyl Ketone B1] Dialkyl ketone B1 (dipentadecyl ketone) was obtained in the same manner as dialkyl ketone A1, except that magnesium palmitate was used as the main raw material.

[0058] [Production Example B2: Preparation of Dialkyl Ketone B2] Dialkyl ketone B1 (dieicosyl ketone) was obtained in the same manner as dialkyl ketone A1, except that magnesium eicosanoate was used as the main raw material.

[0059] [Production Example B3: Preparation of Dialkyl Ketone B3] Dialkyl ketone B3 (ditridecyl ketone) was obtained in the same manner as dialkyl ketone A1, except that magnesium myristate was used as the main raw material.

[0060] [Production Example B4: Preparation of Dialkyl Ketone B4] Dialkyl ketone B4 (dihexacosyl ketone) was obtained in the same manner as dialkyl ketone A1, except that magnesium hexacosanoate was used as the main raw material.

[0061] [Production Example B5: Preparation of Dialkyl Ketone B5] Dialkyl ketone B5 (dihexadecyl ketone) was obtained in the same manner as dialkyl ketone A1, except that magnesium heptadecanoate was used as the main raw material.

[0062] [Summary of Dialkyl Ketone B] The carbon number and average carbon number b of each dialkyl ketone B prepared above are shown below.

Table 2

[0063] (3) Preparation of Fatty Acid Amide C Three types of fatty acid amide C were prepared by the following method.

[0064] [Production Example C1: Preparation of Fatty Acid Amide (Tertiary Amide Compound) C1] In a pressure-resistant glass container, 10.0 g (35 mmol) of stearic acid (product name: NAA (registered trademark)-180, manufactured by NOF Corporation, acid value: 196.7 mgKOH / g) and 10.2 g (140 mmol) of diethylamine were added, and the mixture was shaken in a shaking bath set at 90 °C for 10 minutes. Then, after cooling the contents, 100 g of water was added to obtain a precipitate. The obtained precipitate was further washed with water and dried under vacuum to obtain 8 g of fatty acid amide (tertiary amide compound) C1 (N,N-diethylstearic acid amide).

[0065] [Production Example C2: Preparation of Fatty Acid Amide (Tertiary Amide Compound) C2] Fatty acid amide (tertiary amide compound) C2 (N,N-dipropylstearic acid amide) was obtained in the same manner as in Production Example C1, except that the same molar amount of dipropylamine was used instead of diethylamine.

[0066] [Production Example C3: Preparation of Fatty Acid Amide (Tertiary Amide Compound) C3] Fatty acid amide (tertiary amide compound) C3 (N,N-diethylbehenic acid amide) was obtained in the same manner as in Production Example C1, except that the same molar amount of behenic acid (manufactured by NOF Corporation, behenic acid content: 97% by mass, acid value: 164.9 mgKOH / g) was used instead of stearic acid.

[0067] [Summary of Fatty Acid Amides] The types of alkyl groups of diamines and the number of carbon atoms of monocarboxylic acids used in the synthesis of fatty acid amides are shown below.

Table 3

[0068] (4) Preparation of β-Ketocarboxylic Acid D β-Ketocarboxylic acid D was prepared by the following method.

[0069] [Production Example D1: Synthesis of β-Ketocarboxylic Acid D1] 300 mL of toluene and 50 g (0.17 mol) of stearic acid chloride were added to a 500 mL four-necked flask equipped with a thermometer, a nitrogen inlet tube, a stirring blade, and a cooling tube. While stirring the system, 18.2 g (0.18 mol) of triethylamine was added dropwise. After the addition was complete, the reaction was continued for 2 hours. Then, liquid separation treatment using 50 g of water was carried out 10 times. 1.2 g (0.01 mol) of potassium carbonate and 118.8 g of water were added thereto, and the reaction was carried out at 70 °C for 15 minutes. After standing, the aqueous layer was removed. Further, it was allowed to stand at 50 °C, and the resulting precipitate and the residue of potassium carbonate were removed by filtration. Toluene was distilled off under reduced pressure from the filtrate to obtain 10 g of β-ketocarboxylic acid D1 (2-hexadecyl-3-oxoeicosanoic acid).

[0070] (5) Preparation of Oil Gelling Agent Oil gelling agents (wax compositions) 1 to 14 were prepared by the following method.

[0071] [Preparation of Oil Gelling Agent (Wax Composition) 1] 99.5 g of dialkyl ketone A1 and 0.5 g of dialkyl ketone B1 were taken, heated and dissolved at 90 °C, mixed to be homogeneous, cooled, solidified, and then pulverized to obtain oil gelling agent (wax composition) 1.

[0072] [Preparation of Wax Compositions 2 to 14] As shown in Table 4, except that the ratio and type of dialkyl ketone A and dialkyl ketone B were changed, and fatty acid amide C and β-ketocarboxylic acid D were added as necessary, oil gelling agents (wax compositions) 2 to 14 were obtained in the same manner as oil gelling agent (wax composition) 1.

[0073] The content of fatty acid amide C and the content of β-ketocarboxylic acid D described in Table 4 are the amounts of fatty acid amide C and β-ketocarboxylic acid D when the total amount of dialkyl ketone A and dialkyl ketone B is 100 parts by mass.

[0074]

Table 4

[0075] 2. Preparation of Oil Gel Composition [Preparation of Oil Gel Composition] Take 4.5 g of Pearl Rim EX (manufactured by NOF Corporation) and 0.5 g of Oil Gelator (Wax Composition) 1, melt and mix them at 100 °C on a hot plate in an aluminum pan, and then allow to cool at room temperature for 30 minutes to obtain Oil Gel Composition 1. For the sample for color development evaluation, 0.05 g of Red No. 215 was added, and after melting and mixing in the same manner and allowing to cool, an oil gel composition was obtained.

[0076] [Preparation of Oil Gel Compositions 2 to 16] Oil gel compositions were obtained in the same manner as Oil Gel Composition 1, except that the base oil and the oil gelator were changed to the combinations and contents shown in Table 5. The oils used are as follows. In Oil Gel Composition 16, candelilla wax was used instead of the above-mentioned oil gelator. Pearl Rim EX: Manufactured by NOF Corporation Cetiol SN-1: Manufactured by BASF

[0077] [Table 5]

[0078] [Evaluation] The oil gel compositions prepared above were evaluated by the following methods respectively. The results are shown in Table 6 and Table 7 respectively.

[0079] [Shape Retention (Shear Stress)] Using a viscoelasticity measuring device (MCR 302, manufactured by Anton Paar), the shear stress when the jig was pressed against the sample (oil gel composition) and reciprocated was measured. The evaluation criteria are as follows.

[0080] (Test Conditions (Reciprocating Motion)) Measuring jig: PP25 (disk-shaped) Temperature: 25 °C Strain (swing angle γ): 10% Frequency: 2 Hz Measurement height: 1 mm

[0081] (Evaluation criteria) ◎: Shear stress is 3,000 Pa or more ○: Shear stress is 2,500 Pa or more and less than 3,000 Pa △: Shear stress is 2,000 Pa or more and less than 2,500 Pa ×: Shear stress is less than 2,000 Pa

[0082] <Color development property (chroma)> For the prepared evaluation sample (oil gel composition), the surface of the sample was measured in reflection mode using a color difference meter (color difference meter ZE6000, manufactured by Nippon Denshoku Industries Co., Ltd.), and the values of color development a* and b* for each hue in the CIE1976 (L*, a*, b*) color space (so-called CIELAB) were obtained. Using the obtained measurement values, the chroma C of the evaluation sample was calculated by the following calculation formula. The evaluation criteria are as follows. C = {(a*)2 + (b*)2}1 / 2 ◎: Chroma is 50 or more ○: Chroma is 40 or more and less than 50 △: Chroma is 30 or more and less than 40 ×: Chroma is less than 30

[0083] <Shape retention after high temperature and high humidity storage (shear stress change rate)> The oil gel composition prepared above was left standing under high temperature and high humidity conditions of 50 °C and 90% RH for 72 hours. For the evaluation sample after high temperature and high humidity storage, the shear stress was measured by the method described above. Using the shear stress τ before storage under high temperature and high humidity conditions obtained above and the shear stress τHH after high temperature and high humidity storage, the change rate of the shear stress was calculated from the following formula. Change rate (%) = (|τ - τHH| / τ) × 100 ◎: Change rate of shear stress is less than 2.0% ○: Change rate of shear stress is 2.0% or more and less than 5.0% △: Change rate of shear stress is 5.0% or more and less than 15.0% ×: The change rate of shear stress is 15.0% or more

[0084] <Color development property after high temperature and high humidity storage (chroma change rate)> The oil gel composition prepared above was left standing under high temperature and high humidity conditions of 50 °C and 90% RH for 72 hours. For the evaluation sample after high temperature and high humidity storage, the chroma CHH of the evaluation sample after high temperature and high humidity storage was determined by the method described above. Using the chroma C before storage under the high temperature and high humidity conditions determined above and the chroma CHH after high temperature and high humidity storage, the change rate of chroma was calculated from the following formula. Change rate (%) = (|C - CHH| / C) × 100 The color development property after high temperature and high humidity storage was evaluated based on the change rate of chroma. The evaluation criteria are as follows.

[0085] (Evaluation criteria) ◎: The change rate of chroma is less than 2.0% ○: The change rate of chroma is 2.0% or more and less than 5.0% △: The change rate of chroma is 5.0% or more and less than 15.0% ×: The change rate of chroma is 15.0% or more

[0086] <Oil stain property after high temperature and high humidity storage (filter paper weight change rate)> The prepared evaluation sample was placed on a filter paper whose weight had been measured in advance, and the weight of the filter paper was measured after high temperature and high humidity storage (after leaving standing at 50 °C and 90% RH for 72 hours). Using the filter paper weight W measured in advance and the filter paper weight WHH after high temperature and high humidity storage, the change rate of the filter paper weight was calculated from the following formula. The evaluation criteria are as follows. Change rate of filter paper weight (%) = (|WHH - W| / W) × 100

[0087] (Evaluation criteria) ◎: The change rate of filter paper weight is less than 2.0% ○: The change rate of filter paper weight is 2.0% or more and less than 5.0% △: The change rate of filter paper weight is 5.0% or more and less than 15.0% ×: The change rate of filter paper weight is 15.0% or more

[0088]

Table 6

[0089]

Table 7

[0090] In Tables 6 and 7, the numerical values in parentheses are the measured values or calculated values obtained in the above evaluation. The oil gel compositions of Examples 1 to 12 contain a dialkyl ketone A having 29 to 61 carbon atoms and an average carbon number a, and a dialkyl ketone B having 21 to 55 carbon atoms and an average carbon number b, and the difference (a - b) between the average carbon number a and the average carbon number b is 2 or more and 8 or less, and the mass ratio thereof is 70:30 to 99.9:0.1, that is, the oil gelling agent of the present invention.

[0091] According to the above evaluation results, the oil gel compositions of Examples 1 to 12 containing the oil gelling agent of the present invention are excellent in shape retention (shear stress) and color development (chroma), and even after being exposed to high temperature and high humidity conditions, the shape retention (shear stress change rate) and color development (chroma change rate) are good, and oil staining is also suppressed.

[0092] On the other hand, in Comparative Example 1, an oil gelling agent not containing dialkyl ketone B is used. Although the oil gel composition is excellent in the retention of color development (chroma change rate) after high temperature and high humidity conditions, the results of shape retention (shear stress change rate) and oil stain suppression (filter paper weight change rate) are low, and the initial chroma is also inferior. Further, in Comparative Example 2, an oil gelling agent in which the above content of dialkyl ketone B is 40% by mass is used. Although the oil gel composition is excellent in color development (chroma) and the persistence of shape retention (shear stress change rate) after high temperature and high humidity conditions, it is inferior in shape retention immediately after blending, color development after high temperature and high humidity conditions, and oil stain suppression.

[0093] Comparative Example 3 uses an oil gel composition in which the difference in the number of carbon atoms between dialkyl ketone A and dialkyl ketone B is 10. Although the oil gel composition is excellent in shape retention, color development, and color development after high-temperature and high-humidity conditions, it is inferior in shape retention and oiliness suppression after high-temperature and high-humidity conditions.

[0094] Comparative Example 4 uses candelilla wax, which is a natural wax. Although the oil gel composition has good color development, it is inferior in shape retention, color development after high-temperature and high-humidity conditions, shape retention, and oiliness suppression.

Industrial Applicability

[0095] According to the oil gelling agent of the present invention, an oil gel can be obtained that is excellent in shape retention and color development of the colorant, can maintain shape retention and color development even after being exposed to high-temperature and high-humidity conditions, and can suppress oil stain. Therefore, it is useful in various fields such as cosmetics, quasi-drugs, and daily sundries.

Claims

1. a dialkyl ketone A having 29 to 61 carbon atoms and an average carbon number of a, and a dialkyl ketone B having 21 to 55 carbon atoms and an average carbon number of b, and contains the difference (a - b) between a and b is 2 or more and 8 or less, and the mass ratio of the dialkyl ketone A to the dialkyl ketone B is 70:30 to 99.9:0.1, an oil gelling agent.

2. Based on 100 parts by mass of the total amount of the dialkyl ketone A and the dialkyl ketone B, containing 0.1 to 5 parts by mass of a fatty acid amide C obtained from a monovalent carboxylic acid having 16 to 24 carbon atoms and a dialkylamine, the oil gelling agent according to Claim 1.

3. Based on 100 parts by mass of the total amount of the dialkyl ketone A and the dialkyl ketone B, containing 0.01 to 2% by mass of β-ketocarboxylic acid, the oil gelling agent according to Claim 1.

4. An oil gel containing the oil gelling agent according to any one of Claims 1 to 3 and an oil, and containing 0.1 to 30 parts by mass of the oil gelling agent with respect to 100 parts by mass of the oil.

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