wax composition

Abstract

The present invention provides a wax composition that can impart stable frictional force to oils and resins in response to temperature changes. [Solution] A wax composition comprising a secondary alcohol A having 11 to 61 carbon atoms and a dialkylketone B having 11 to 61 carbon atoms, wherein the mass ratio of the secondary alcohol A to the dialkylketone B is 70:30 to 99.9:0.1.

Description

Technical Field

[0001] The present invention relates to a wax composition, and more particularly to a wax composition mainly composed of a secondary alcohol.

Background Art

[0002] Since wax exhibits lubricity, water resistance, plasticity, glossiness, etc., it is used in various applications as an additive for the purpose of improving the functionality of various materials. Generally, wax-like solid esters or paraffin waxes are used as wax. The former is a synthetic ester wax composed of a higher fatty acid and a higher alcohol, and the latter is obtained by refining petroleum. Wax is added to a resin and used, for example, to control the hardness, water repellency or surface smoothness of the resin. The solid (wax) state wax can be heated to a temperature above the melting point to cause a phase change to a liquid state and then mixed with various materials for use. Specific uses of wax include, for example, a release agent for toner, a release agent for molds used in metal forming processes, a shape retention agent for cosmetics such as lipstick or lip cream, and a lubricity improver used in a rubber coating agent, etc.

[0003] Also, higher alcohols may be used as wax. Patent Document 1 discloses an oil-in-water cosmetic composition containing a higher alcohol. Patent Document 2 discloses a resin composition containing a higher alcohol as a lubricant.

[0004] In addition, in oily compositions such as cosmetic compositions and resin compositions, it is desirable to exhibit constant performance even when the temperature changes greatly from the hot summer to the cold winter, so an improvement in performance stability against temperature changes is required.

Prior Art Documents

Patent Documents

[0005] [Patent Document 1] Japanese Patent Publication No. 2023-140504 [Patent Document 2] International Publication No. 2016 / 132743 [Overview of the project] [Problems that the invention aims to solve]

[0006] This invention has been made in view of the above problems, and aims to provide a wax composition that can impart stable frictional force to oils and resins in response to temperature changes. [Means for solving the problem]

[0007] Generally, linear primary alcohols are used as higher alcohols added as waxes to oily compositions or resin compositions. On the other hand, the present inventors conducted diligent research to solve the above problems and found that a wax composition containing a specific secondary alcohol and a dialkyl ketone in a specific ratio exhibits less viscosity fluctuation with temperature changes, and that oily compositions and resin compositions containing such a wax composition have stable frictional force with respect to temperature changes, thus completing the present invention.

[0008] In other words, the present invention is as follows: A wax composition comprising a secondary alcohol A having 11 to 61 carbon atoms and a dialkylketone B having 11 to 61 carbon atoms, wherein the mass ratio of the secondary alcohol A to the dialkylketone B (secondary alcohol A:dialkylketone B) is 70:30 to 99.9:0.1. [Effects of the Invention]

[0009] The wax composition of the present invention can impart stable frictional force to oils and resins against temperature changes. [Modes for carrying out the invention]

[0010] The embodiments of the present invention will be described below, but the present invention is not limited to the embodiments described herein and can be modified in various ways without departing from the spirit of the invention. Furthermore, in this invention, a numerical range defined using the symbol "~" includes the numerical values ​​at both ends (upper and lower limits) of "~". For example, "2~10" represents the range of 2 to 10. Furthermore, in this invention, the notations C1, C2, C3, etc., relating to a compound represent the number of carbon atoms in the compound, and the range C1-20, etc., represents the range of carbon atoms in the compound. Furthermore, within the numerical range described in the present invention, the upper or lower limit of that numerical range can be replaced with the values ​​shown in the examples or values ​​uniquely derived from the examples. Furthermore, unless otherwise specified, the numerical values ​​described in this invention are obtained by rounding a digit that was one place smaller than the smallest digit contained in the numerical value.

[0011] The wax composition of the present invention comprises a secondary alcohol A having 11 to 61 carbon atoms and a dialkylketone B having 11 to 61 carbon atoms, characterized in that the mass ratio of the secondary alcohol A to the dialkylketone B (secondary alcohol A:dialkylketone B) is 70:30 to 99.9:0.1. Furthermore, secondary alcohols and dialkylketones generally exhibit molecular weight distributions when analyzed by gel permeation chromatography (GPC). Therefore, in this invention, "number of carbon atoms" refers to the distribution of carbon atoms as analyzed by gel permeation chromatography (GPC). Note that "number of carbon atoms" refers to the number of carbon atoms in one molecule. Also, a carbon number of 11 to 61 means that the distribution of carbon atoms falls within the range of 11 to 61, and does not necessarily mean that the distribution of carbon atoms extends from 11 to 61. The wax composition of the present invention contains the above-mentioned specific secondary alcohol A and dialkylketone B in the above-mentioned specific mass ratio. As a result, the crystallinity of secondary alcohol A is moderately reduced by dialkylketone B, and consequently, the crystallization rate and molecular orientation of the wax composition are easily controlled, localized crystallization is suppressed, and viscosity fluctuations due to temperature changes are suppressed. Therefore, by incorporating the wax composition of the present invention into an oil or resin, a stable frictional force against temperature changes can be imparted to them. Cosmetic oils can exhibit a stable sense of thickness due to having a stable frictional force. Resins can exhibit stable slipperiness due to having a stable frictional force. Lubricating oils can exhibit stable lubricity due to having a stable frictional force. In this invention, "sense of thickness" refers to the feeling of the thickness of the sample between the finger or hand and the skin when the sample is spread on the skin with the finger or hand. Furthermore, in the wax composition of the present invention, the crystallinity or molecular orientation of the wax composition can be controlled by adjusting the chain length of the organic group of secondary alcohol A or the alkyl group of dialkylketone B. This further suppresses the viscosity fluctuations of the wax composition of the present invention with respect to temperature changes, thereby further improving the stability of the frictional force applied to the oil or resin against temperature changes. The following describes each component contained in the wax composition of the present invention.

[0012] [Secondary Alcohol A] The wax composition of the present invention contains a secondary alcohol A having 11 to 61 carbon atoms. This secondary alcohol A is a compound that contains one hydroxyl group, and organic groups are bonded to both sides of the carbon atom to which the hydroxyl group is attached. That is, of the remaining three bonds of the carbon atom to which the hydroxyl group is attached, two are bonded to organic groups and one is bonded to a hydrogen atom. Furthermore, the number of carbon atoms in one molecule of this secondary alcohol A is 11 to 61. The secondary alcohol A contained in the wax composition of the present invention may consist of a single compound, or, as described above, may be a mixture having a certain molecular weight distribution, that is, a mixture of two or more compounds. In order to impart a desired frictional force to an oil or resin using the wax composition of the present invention, and to improve the stability of the frictional force imparted by the wax composition of the present invention against temperature changes, the wax composition of the present invention preferably contains at least a secondary alcohol A having 13 to 57 carbon atoms, and more preferably contains at least a secondary alcohol A having 25 to 40 carbon atoms. Furthermore, when the total mass of secondary alcohol A is 100% by mass, the content of such preferred secondary alcohol A is preferably 70% by mass or more, more preferably 80% by mass or more, and even more preferably 90% by mass or more.

[0013] The carbon number of the secondary alcohol A may be 11 to 61, but is preferably 11 to 51, more preferably 21 to 41, from the standpoint of imparting a desired frictional force to the oil or resin with the wax composition of the present invention, and improving the stability of the frictional force imparted by the wax composition of the present invention against temperature changes.

[0014] Furthermore, in order to impart a desired frictional force to an oil or resin using the wax composition of the present invention, and to improve the stability of the frictional force imparted by the wax composition of the present invention against temperature changes, it is preferable that the content of the above-mentioned secondary alcohol A in the alcohol contained in the wax composition of the present invention be 99% by mass or more, and more preferably 99.9% by mass or more.

[0015] The two organic groups of the secondary alcohol A described above are preferably hydrocarbon groups, more preferably saturated or unsaturated aliphatic groups, and even more preferably alkyl groups, in order to impart the desired frictional force to the oil or resin by the wax composition of the present invention.

[0016] The two organic groups of the secondary alcohol A may be the same or different. On the other hand, from the viewpoint of improving the stability of the frictional force imparted by the wax composition of the present invention against temperature changes, the difference in the number of carbon atoms of the two organic groups of the secondary alcohol A is preferably 2 or less, more preferably 0.

[0017] The organic group of the secondary alcohol A may be linear, branched, or cyclic. However, from the viewpoint of imparting a desired frictional force to an oil or resin by the wax composition of the present invention, and improving the stability of the frictional force imparted by the wax composition of the present invention against temperature changes, it is preferably linear.

[0018] Specific examples of the secondary alcohol A include 6-undecanol, 8-pentadecanol, 10-nonadecanol, 12-tricosanol, 14-heptacosanol, 16-hentriacontanol, 18-pentatriacontanol, 20-nonatriacontanol, 22-tritetracosanol, 24-heptatetracosanol, 26-henpentacosanol, 28-pentapentacosanol, and the like. Among them, from the viewpoint of imparting a desired frictional force to an oil or resin by the wax composition of the present invention, and improving the stability of the frictional force imparted by the wax composition of the present invention against temperature changes, at least one selected from the group consisting of 16-hentriacontanol, 18-pentatriacontanol, and 20-nonatriacontanol is preferably used.

[0019] The method for preparing the secondary alcohol A is not particularly limited. For example, in the presence of a metal oxide catalyst, a carboxylic acid having a desired organic group is reacted at a high temperature (preferably a temperature of 300 to 350 ° C) and a high pressure (preferably 0.1 to 5 MPa), decarboxylated to obtain a ketone, and the obtained ketone is reduced to obtain the secondary alcohol A.

[0020] Examples of possible metal oxide catalysts include magnesium oxide, calcium oxide, zinc oxide, and the like. The carboxylic acid having a desired organic group is not particularly limited, and examples thereof include caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, and the like.

[0021] On the other hand, instead of the above carboxylic acid and metal oxide catalyst, a metal carboxylate such as magnesium carboxylate, calcium carboxylate, or zinc carboxylate may be used to obtain a ketone. Representative examples of the metal carboxylate 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.

[0022] The reduction method for reducing the ketone is not particularly limited, and for example, catalytic reduction by reacting hydrogen in the presence of a hydrogenation catalyst, hydride reduction using sodium borohydride or the like, Ruché reduction, silane reduction, Meerwein-Pondorf-Varley reduction, Wolff-Kishner reduction, and other known methods can be used.

[0023] 〔Dialkyl Ketone B〕 The wax composition of the present invention contains a dialkyl ketone B having 11 to 61 carbon atoms. The dialkyl ketone B is a compound containing one carbonyl group and having alkyl groups bonded to both sides of the carbon atom in the carbonyl group, and the number of carbon atoms in one molecule is 11 to 61. The dialkyl ketone B contained in the wax composition of the present invention may be composed of a single compound, or may be a mixture having a certain molecular weight distribution as described above, that is, a mixture of two or more compounds. In terms of imparting a desired frictional force to an oil or resin with the wax composition of the present invention, and improving the stability of the frictional force imparted by the wax composition of the present invention against temperature changes, the wax composition of the present invention preferably contains at least a dialkylketone B having 13 to 57 carbon atoms, and more preferably contains at least a dialkylketone B having 25 to 40 carbon atoms. Furthermore, when the total mass of dialkylketone B is 100% by mass, the content of such preferred dialkylketone B is preferably 70% by mass or more, more preferably 80% by mass or more, and even more preferably 90% by mass or more.

[0024] The number of carbon atoms in the above-mentioned dialkylketone B may be 11 to 61, but is preferably 11 to 51, and more preferably 21 to 41, from the standpoint of imparting a desired frictional force to an oil or resin with the wax composition of the present invention, and improving the stability of the frictional force imparted by the wax composition of the present invention against temperature changes.

[0025] Furthermore, in order to impart a desired frictional force to an oil or resin using the wax composition of the present invention, and to improve the stability of the frictional force imparted by the wax composition of the present invention against temperature changes, it is preferable that the content of the above-mentioned dialkylketone B among the ketones contained in the wax composition of the present invention be 99% by mass or more, and more preferably 99.9% by mass or more.

[0026] The two alkyl groups of the dialkylketone B described above may be the same or different. On the other hand, in order to improve the stability of the frictional force imparted by the wax composition of the present invention against temperature changes, the difference in the number of carbon atoms between the two alkyl groups of the dialkylketone B described above is preferably 2 or less, and more preferably 0.

[0027] The alkyl group of the dialkylketone B may be linear, branched, or cyclic, but it is preferable that it be linear, in order to impart a desired frictional force to the oil or resin with the wax composition of the present invention, and to improve the stability of the frictional force imparted by the wax composition of the present invention against temperature changes.

[0028] Specific examples of the above-mentioned dialkylketone B include diheptylketone, didecylketone, diundecylketone, didodecylketone, ditridecylketone, ditetradecylketone, dipentadecylketone, dihexadecylketone, diheptadecylketone, heptadecylpentadecylketone, dioctadecylketone, dinonanedecylketone, dieicosylketone, diheneicosylketone, didcosylketone, ditricosylketone, ditetracosylketone, dihexacosylketone, diheptacosylketone, and dioctacosylketone. Among these, at least one selected from the group consisting of dihexadecylketone, diheptadecylketone, and dioctadecylketone is preferably used, in order to impart a desired frictional force to the oil or resin with the wax composition of the present invention and to improve the stability of the frictional force imparted by the wax composition of the present invention with respect to temperature changes.

[0029] The method for preparing the above-mentioned dialkylketone B is not particularly limited. For example, it can be prepared in the same manner as the method used to obtain the ketone as an intermediate in the preparation of the secondary alcohol A described above. That is, the above-mentioned dialkylketone B can be obtained by reacting a saturated fatty acid having a desired number of carbon atoms with a metal oxide catalyst at high temperature and high pressure, and then decarboxylating it. Alternatively, the above-mentioned dialkylketone B can be obtained by using a saturated fatty acid metal salt instead of the saturated fatty acid and metal oxide catalyst.

[0030] [Wax composition] The wax composition of the present invention contains the above-mentioned secondary alcohol A and the above-mentioned dialkylketone B in a mass ratio (secondary alcohol A:dialkylketone B) of 70:30 to 99.9:0.1. The above mass ratio (which may be denoted as "A:B" in the present invention) may be 70:30 to 99.9:0.1, but from the standpoint of imparting a desired frictional force to an oil or resin by the wax composition of the present invention, and from the standpoint of improving the stability of the frictional force imparted by the wax composition of the present invention with respect to temperature changes, it is preferably 80:20 to 99.9:0.1, more preferably 90:10 to 99.5:0.5, and even more preferably 93:7 to 99:1.

[0031] When the total mass of the wax composition of the present invention is 100 parts by mass, the total content of the secondary alcohol A and the dialkylketone B is not particularly limited, but is preferably 90 parts by mass or more, more preferably 95 parts by mass or more, even more preferably 99 parts by mass or more, and may be 100 parts by mass, from the standpoint of easily exhibiting the effects of the present invention.

[0032] When the number of carbon atoms in the compound with the highest content among the compounds constituting secondary alcohol A is denoted as the number of carbon atoms a of secondary alcohol A, and the number of carbon atoms in the compound with the highest content among the compounds constituting dialkylketone B is denoted as the number of carbon atoms b of dialkylketone B, the absolute value of the difference between a and b (|ab|) is not particularly limited, but is preferably 0 to 20, more preferably 0 to 10, and even more preferably 0 to 2. When the difference between the number of carbon atoms a and the number of carbon atoms b is within the above range, the crystallinity of secondary alcohol A can be appropriately controlled by dialkylketone B, thereby further improving the stability of the frictional force imparted by the wax composition of the present invention against temperature changes. Furthermore, from a similar viewpoint, it is preferable that the number of carbon atoms a is greater than the number of carbon atoms b. When the secondary alcohol A is composed of a single compound, the carbon number a is the carbon number of the single compound constituting the secondary alcohol A. When the dialkyl ketone B is composed of a single compound, the carbon number b is the carbon number of the single compound constituting the dialkyl ketone B. The compound with the highest content in the mixture can be identified by GC measurement under the following conditions. <GC measurement conditions> Apparatus: SHIMAZU GC-2030 Column: Agilent DB-1HT 15m×0.25mm×0.10μm Carrier gas: Nitrogen Gas flow rate: 134.4 mL / min (split, 50) Inlet temperature: 400 °C Detector (temperature): FID (400 °C) Column temperature (heating rate): 100 °C - 390 °C (10 °C / min) Measurement sample: Toluene solution (10 mg / g) Analysis: Area %

[0033] 〔Method for producing wax composition〕 The method for producing the wax composition of the present invention is not particularly limited. For example, after separately synthesizing the above-mentioned secondary alcohol A and dialkyl ketone B, the wax composition of the present invention can be obtained by mixing them. When mixing the separately synthesized components, it is preferable to heat and dissolve them at a temperature not lower than the melting point of each component and mix them uniformly. Further, thereafter, it is preferable to cool and solidify the heated and dissolved mixture and perform a fine particle treatment such as pulverization or granulation to produce the wax composition of the present invention. Thereby, the variation in the quality of the obtained wax composition can be suppressed. On the other hand, after obtaining the dialkyl ketone B, a part of it may be reduced to obtain the secondary alcohol A, thereby synthesizing the secondary alcohol A and the dialkyl ketone B together.

[0034] 〔Uses of wax composition〕 The wax composition of the present invention is typically used in combination with an oil or resin. The oils used in combination with the wax composition of the present invention are not particularly limited, but examples include oils for cosmetics that can be used as a base oil for cosmetics, and oils for lubricating oils that can be used as a base oil for lubricating oils. The resin used in combination with the wax composition of the present invention may be any general-purpose resin that has been conventionally used, and is not particularly limited. Specific applications of the wax composition of the present invention are not particularly limited, but examples include cosmetic additives, lubricating oil additives, and resin lubricants. The wax composition of the present invention, which is to be contained in an oil or resin, may be a single type or a combination of two or more types.

[0035] In cosmetics, the cosmetic oil used in combination with the wax composition of the present invention is not particularly limited, and examples include oils conventionally used as base oils for cosmetics, such as hydrocarbon oils, branched fatty acids, aliphatic alcohols, ester oils, and ether oils. Examples of hydrocarbon oils include squalane, squalene, liquid paraffin, α-olefin oligomer, hydrogenated polyisobutene, and isoparaffin. Examples of branched fatty acids include 2-ethylhexanoic acid, isononanoic acid, isopalmitic acid, isostearic acid, and isobehenic acid. Examples of aliphatic alcohols include branched primary alcohols such as isostearyl alcohol, octyldodecanol, hexyldecanol, and decyltetradecanol, as well as unsaturated aliphatic primary alcohols such as oleyl alcohol. Examples of ester oils 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 triglycerides, neopentyl glycol dicaprate, 2-ethylhexyl isononanoate, isononyl isononanoate, isodecyl isononanoate, isotridecyl isononanoate, hexyl laurate, ilopropyl myristate, and 2-hexyl myristate. Examples include rudecyl, 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-stearolylstearate, oleyl oleate, 2-ethylhexyl salicylate, and dialkyl carbonate. Examples of ether oils include dioctyl ether and polyoxyethylene polyoxypropylene dimethyl ether.

[0036] In lubricating oils, the lubricating oil agent used in combination with the wax composition of the present invention is not particularly limited, and examples include oils conventionally used as base oils for lubricating oils, such as mineral oil, highly refined mineral oil, animal and vegetable oils and fats, synthetic esters, poly-α-olefins, and GTL (gas-to-liquid) oils.

[0037] As an oil used in combination with the wax composition of the present invention, at least one selected from the group consisting of hydrocarbon oils and ester oils is preferred, with hydrocarbon oils being more preferred, in order to easily exhibit the effects of the wax composition of the present invention. Furthermore, hydrogenated polyisobutene is preferred as the hydrocarbon oil, and cetyl 2-ethylhexanoate is preferred as the ester oil.

[0038] When the wax composition of the present invention is used in combination with an oil, the content of the wax composition of the present invention per 100 parts by mass of the oil is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, and even more preferably 3 to 10 parts by mass, in order to easily exert the effects of the wax composition of the present invention.

[0039] The resin used in combination with the wax composition of the present invention is not particularly limited and may be a general-purpose resin that has been conventionally used, such as polyolefins such as polyethylene and polypropylene; conventionally used engineering plastics such as polycarbonate, polyethylene terephthalate, polyamide, polyacetal and modified polyphenylene ether; thermosetting resins such as phenolic resins and epoxy resins; conventionally used super engineering plastics such as aromatic polyamide and polyphenylene sulfide; and elastomers such as ethylene vinyl acetate copolymer, olefin-based elastomer and styrene butadiene rubber (SBR). Among these, conventionally used engineering plastics and elastomers are preferred because they allow the effects of the wax composition of the present invention to be easily exhibited.

[0040] When the wax composition of the present invention is used by mixing it with a resin, the content of the wax composition of the present invention per 100 parts by mass of resin is preferably 0.01 to 20 parts by mass, more preferably 0.05 to 10 parts by mass, and even more preferably 0.1 to 6 parts by mass, in order to easily exert the effects of the wax composition of the present invention. [Examples]

[0041] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to the following examples. Unless otherwise specified, parts and percentages are based on mass.

[0042] [Preparation of wax composition] (1) Preparation of secondary alcohol A Five types of secondary alcohol A were prepared using the following method.

[0043] (Synthesis Example 1) Synthesis of secondary alcohol A1 (18-pentatriacontanol) 700.0 g of magnesium stearate was weighed into a 1 L stainless steel separable flask, and the system was heated to 250°C under nitrogen bubble injection. Then, nitrogen was injected under pressure of 2 MPa, and the system temperature was raised to 340-350°C, and the reaction was continued for 8 hours. Subsequently, the reaction product was cooled to 100°C to obtain the crude ketone product. Under nitrogen bubble injection at 100°C, the obtained crude ketone product was filtered using a 100-mesh metal strainer to remove the magnesium oxide produced as a by-product. The filtered ketone (diheptadecyl ketone) was discharged into a stainless steel tray, solidified at room temperature, and pulverized in a mixer to obtain 540 g of diheptadecyl ketone. The obtained diheptadecyl ketone was reduced by reacting it with 10 g of sodium borohydride in toluene solvent to obtain 488 g of secondary alcohol A1 (18-pentatriacontanol).

[0044] (Synthesis Example 2) Synthesis of Secondary Alcohol A2 (28-Pentapentacontanol) Secondary alcohol A2 (28-pentapentacontanol) was obtained by the same procedure as in Synthesis Example 1, except that magnesium montanate was used instead of magnesium stearate as the main raw material.

[0045] (Synthesis Example 3) Synthesis of Secondary Alcohol A3 (8-Pentadecanol) Secondary alcohol A3 (8-pentadecanol) was obtained by the same procedure as in Synthesis Example 1, except that magnesium caprylate was used instead of magnesium stearate as the main raw material.

[0046] (Synthesis Example 4) Synthesis of Secondary Alcohol A4 (4-Heptanol) Secondary alcohol A4 (4-heptanol) was obtained by the same procedure as in Synthesis Example 1, except that magnesium butanoate was used instead of magnesium stearate as the main raw material.

[0047] (Synthesis Example 5) Synthesis of Secondary Alcohol A5 (3,4-Heptahexacontanol) Secondary alcohol A5 (3,4-heptahexacontanol) was obtained by the same procedure as in Synthesis Example 1, except that magnesium tetratriacontanate was used instead of magnesium stearate as the main raw material.

[0048] (2) Preparation of dialkylketone B Five types of dialkylketone B were prepared using the following method.

[0049] (Synthesis Example 6) Synthesis of Dialkylketone B1 (Diheptadecylketone) Dialkylketone B1 (diheptadecylketone) was obtained using the same procedure as in Synthesis Example 1 to obtain the ketone (diheptadecylketone).

[0050] (Synthesis Example 7) Synthesis of Dialkylketone B2 (Diheptacosylketone) Except for using magnesium montanate instead of magnesium stearate as the main raw material, dialkylketone B2 (diheptacosylketone) was obtained by the same procedure as in Synthesis Example 1 for obtaining the ketone (diheptadecylketone).

[0051] (Synthesis Example 8) Synthesis of dialkylketone B3 (diheptyl ketone) Except for using magnesium caprylate instead of magnesium stearate as the main raw material, dialkylketone B3 (diheptyl ketone) was obtained by the same procedure as in Synthesis Example 1 to obtain the ketone (diheptadecyl ketone).

[0052] (Synthesis Example 9) Synthesis of Dialkylketone B4 (Dipropyl Ketone) Except for using magnesium butanoate instead of magnesium stearate as the main raw material, dialkylketone B4 (dipropyl ketone) was obtained by the same procedure as in Synthesis Example 1 for obtaining the ketone (diheptadecyl ketone).

[0053] (Synthesis Example 10) Synthesis of Dialkylketone B5 (Ditritriacontanyl Ketone) Except for using magnesium tetratriacontanate instead of magnesium stearate as the main raw material, dialkylketone B5 (ditritricontanyl ketone) was obtained by the same procedure as in Synthesis Example 1 to obtain the ketone (diheptadecyl ketone).

[0054] Table 1 shows the compound names and carbon numbers of secondary alcohols A1 to A5 obtained in Synthesis Examples 1 to 5, and Table 2 shows the compound names and carbon numbers of dialkylketones B1 to B5 obtained in Synthesis Examples 6 to 10.

[0055] [Table 1]

[0056] [Table 2]

[0057] (3) Preparation of wax composition The wax compositions (wax compositions W1 to W12) were prepared using the following method.

[0058] [Preparation of wax composition W1] 99 g of secondary alcohol A1 and 1 g of dialkylketone B1 were taken, heated and dissolved at 90°C, mixed until homogeneous, cooled and solidified, and then pulverized to obtain wax composition W1.

[0059] [Preparation of wax compositions W2 to W12] Wax compositions W2 to W12 were obtained in the same manner as wax composition 1, except that the combination or mass ratio of secondary alcohol A and dialkylketone B was changed according to Table 3.

[0060] Table 3 shows the secondary alcohol A and dialkylketone B contained in wax compositions W1 to W12, the mass ratio of secondary alcohol A to dialkylketone B (A:B), and the difference (|ab|) between the number of carbon atoms a of secondary alcohol A and the number of carbon atoms b of dialkylketone B.

[0061] [Table 3]

[0062] The wax compositions W1 to W8 were the wax compositions of the present invention, comprising a secondary alcohol A having 11 to 61 carbon atoms and a dialkyl ketone B having 11 to 61 carbon atoms, with the mass ratio of secondary alcohol A to dialkyl ketone B being in the range of 70:30 to 99.9:0.1. Furthermore, the difference (|ab|) between the number of carbon atoms a of secondary alcohol A and the number of carbon atoms b of dialkyl ketone B in the wax compositions W1 to W8 was 0 or more and 20 or less. On the other hand, wax composition W9 consisted only of secondary alcohol A and did not contain dialkylketone B. The wax composition W10 had a mass ratio (A:B) of secondary alcohol A to dialkylketone B of 60:40, which was outside the range of 70:30 to 99.9:0.1. The wax composition W11 contained a secondary alcohol with 7 carbon atoms and a dialkyl ketone with 7 carbon atoms instead of secondary alcohol A with 11 to 61 carbon atoms and dialkyl ketone B with 11 to 61 carbon atoms. The wax composition W12 contained a secondary alcohol with 67 carbon atoms and a dialkyl ketone with 67 carbon atoms instead of secondary alcohol A with 11 to 61 carbon atoms and dialkyl ketone B with 11 to 61 carbon atoms.

[0063] [Example 1: Preparation of cosmetic composition C1] A liquid cosmetic composition C1 was prepared by taking 4.75 g of Pearlream EX (manufactured by NOF Corporation) as a base oil and 0.25 g of wax composition W1, and melting and mixing them at 100°C on a hot plate in an aluminum pan.

[0064] [Examples 2-9 and Comparative Examples 1-4: Preparation of cosmetic compositions C2-C13] Liquid cosmetic compositions C2 to C13 were prepared in the same manner as cosmetic composition C1, except that the combination of base oil and wax composition was changed according to Table 4. The base oils used are as follows: Pearlream EX: Manufactured by NOF Corporation, hydrogenated polyisobutene Cetiol SN-1: Cetyl ethylhexanoate, manufactured by BASF.

[0065] [Evaluation of cosmetic compositions] The following evaluations were performed on the obtained cosmetic compositions C1 to C13. A Bowden tester, artificial leather, and test oil (cosmetic composition) were placed in a constant temperature bath set to 5°C or 40°C and left for 30 minutes. Afterward, the artificial leather was attached to the base, and 1 mL of test oil was dropped onto it. A contactor (surface contact, 1 cm × 1 cm) with the artificial leather attached was pressed against the artificial leather with the test oil, and the device was slid under the conditions of load: 50 g, speed: 10 mm / s, and measurement distance: 20 mm to measure the coefficient of dynamic friction. The average value of the coefficient of dynamic friction was calculated after 10 tests and was defined as the coefficient of dynamic friction (μ) for this test. Based on the value of the coefficient of dynamic friction (μ), the frictional force of the test oil was evaluated according to the following evaluation criteria. A larger value of the coefficient of dynamic friction (μ) indicates greater frictional force and increased thickness, while a smaller value of the coefficient of dynamic friction (μ) indicates less frictional force and decreased thickness. The closer the value of the coefficient of dynamic friction (μ) is to a value between 1.2 and 1.5, the more appropriate the thickness is considered to be in terms of frictional force. Table 4 shows the evaluation results, along with the value of the coefficient of dynamic friction (μ) in parentheses. <Evaluation Criteria> ◎: Dynamic friction coefficient is 1.2 or higher and less than 1.5 ○: The coefficient of dynamic friction is 1.0 or more but less than 1.2 or 1.5 or more but less than 1.7 △: Dynamic friction coefficient is 0.8 or higher but less than 1.0 or 1.7 or higher but less than 2.0 ×: The coefficient of kinetic friction is less than 0.8 or 2.0 or higher.

[0066] Using the values ​​of the coefficient of dynamic friction (μ) in the 5°C test and the 40°C test, the rate of change of the coefficient of dynamic friction due to temperature change was calculated according to the following formula. Based on this rate of change, the stability of the frictional force of the test oil with respect to temperature changes was evaluated according to the evaluation criteria below. Table 4 shows the evaluation results, along with the value of the rate of change (in %) in parentheses. Rate of change (%) = |(value at 5°C) - (value at 40°C)| / (value at 40°C) × 100 <Evaluation Criteria> ◎: Change rate is less than 5.0% ○: Change rate is 5.0% or more and less than 10.0% △: Rate of change is between 10.0% and less than 15.0% ×: Change rate is 15.0% or higher

[0067] [Table 4]

[0068] Comparative Example 1, cosmetic composition C10, which contained wax composition W9, lacked dialkylketone B in wax composition W9. As a result, the coefficient of dynamic friction (μ) decreased at 40°C, and the rate of change when comparing the coefficient of dynamic friction (μ) at 5°C and the coefficient of dynamic friction (μ) at 40°C was high at 20.5%, indicating poor stability of frictional force with respect to temperature changes. In Comparative Example 2, cosmetic composition C11 containing wax composition W10, the amount of dialkylketone B in wax composition W10 was too high, resulting in an increase in the coefficient of dynamic friction (μ) at 5°C. The rate of change when comparing the coefficient of dynamic friction (μ) at 5°C and the coefficient of dynamic friction (μ) at 40°C was high at 27.5%, indicating poor stability of frictional force with respect to temperature changes. The cosmetic composition C12 of Comparative Example 3, which contains the wax composition W11, had a low coefficient of dynamic friction (μ) at 5°C and 40°C, meaning it had low frictional force and insufficient thickness, because the number of carbon atoms in the secondary alcohol and dialkyl ketone contained in the wax composition W11 was too small. Furthermore, the rate of change when comparing the coefficient of dynamic friction (μ) at 5°C and the coefficient of dynamic friction (μ) at 40°C was high at 30.5%, indicating poor stability of frictional force with respect to temperature changes. In Comparative Example 4, cosmetic composition C13 containing wax composition W12, the number of carbon atoms in the secondary alcohol and dialkyl ketone contained in wax composition W12 was too large, resulting in a high coefficient of dynamic friction (μ) at 5°C and 40°C, meaning the frictional force was large and the thickness felt excessive. Furthermore, the rate of change when comparing the coefficient of dynamic friction (μ) at 5°C and the coefficient of dynamic friction (μ) at 40°C was high at 19.7%, indicating poor stability of the frictional force with respect to temperature changes. In contrast, cosmetic compositions C1 to C9 of Examples 1 to 9 contained one of the wax compositions W1 to W8 of the present invention, resulting in a dynamic friction coefficient (μ) at both 5°C and 40°C being between 0.8 and 2.0, and the rate of change when comparing the dynamic friction coefficient (μ) at 5°C and 40°C was low, less than 15.0%. Therefore, cosmetic compositions C1 to C9, by containing the wax composition of the present invention, were given a friction force that exhibited a moderate thickness, and furthermore, possessed a friction force that was stable against temperature changes.

[0069] [Example 10: Preparation of resin composition R14] 0.05 g of wax composition W1 was weighed out and mixed with 0.95 g of ethylene vinyl acetate copolymer (product name: UltraCen® 685, manufactured by Tosoh Corporation) and 49 g of solvent (toluene) to prepare resin composition R14.

[0070] [Examples 11-18 and Comparative Examples 5-8: Preparation of resin compositions R15-R26] Resin compositions R15 to R26 were prepared in the same manner as resin composition R14, except that the combination of resin and wax composition was changed according to Table 5. The resins used are as follows: UltraSen 685: Manufactured by Tosoh Corporation, ethylene vinyl acetate copolymer. JSR 1500: Manufactured by JSR Corporation, styrene-butadiene rubber

[0071] [Evaluation of resin compositions] The following evaluations were performed on the obtained resin compositions R14 to R26. A resin composition was applied to a glass substrate using a bar coater and dried on a hot plate at 100°C for 30 minutes, forming a 1 mm thick resin film. The resulting resin film was subjected to a Bowden tester under the following conditions: contact (semi-cylindrical stainless steel, 1 cm), load: 100 g, speed: 2.5 mm / s, and measurement distance: 10 mm, and the coefficient of dynamic friction was measured. The average value of the coefficient of dynamic friction was calculated after 10 tests and was defined as the coefficient of dynamic friction (μ) for this test. Based on the value of the coefficient of dynamic friction (μ), the frictional force of the resin film was evaluated according to the following evaluation criteria. A smaller value of the coefficient of dynamic friction (μ) indicates lower frictional force and better sliding properties of the resin film. Table 5 shows the evaluation results, along with the value of the coefficient of dynamic friction (μ) in parentheses. <Evaluation Criteria> ◎: The coefficient of kinetic friction is less than 0.200. ○: The coefficient of kinetic friction is 0.200 or more and less than 0.250. △: The coefficient of kinetic friction is 0.250 or higher and less than 0.300. ×: The coefficient of kinetic friction is 0.300 or higher.

[0072] The resin film obtained above was stored in a constant temperature chamber at -20°C and 10% humidity for 12 hours, and then stored in a constant temperature chamber at 90°C and 90% humidity for 12 hours. This temperature cycle was repeated 10 times to perform a cycle test. The coefficient of dynamic friction (μ) of the resin film after the cycle test was determined in the same manner as above. Using the value of the coefficient of dynamic friction (μ) of the resin film before the cycle test (initial value) and the value of the coefficient of dynamic friction (μ) of the resin film after the cycle test (post-cycle test value), the rate of change of the coefficient of dynamic friction before and after the cycle test was calculated according to the following formula. Based on this rate of change, the stability of the frictional force of the resin film with respect to temperature changes was evaluated according to the following evaluation criteria. Table 5 shows the evaluation results, along with the value of the rate of change (unit: %) in parentheses. Rate of change (%) = |(Initial value) - (Value after cycle test)| / (Initial value) × 100 <Evaluation Criteria> ◎: Change rate is less than 3.0% ○: Change rate is 3.0% or more and less than 5.0% △: Rate of change is 5.0% or more but less than 10.0% ×: Change rate is 10.0% or more

[0073] [Table 5]

[0074] Comparative Example 5, resin composition R23, which contained wax composition W9, did not contain dialkylketone B in wax composition W9, resulting in a high rate of change in the dynamic friction coefficient before and after the cycle test of 10.4%, and poor stability of frictional force against temperature changes. In Comparative Example 6, the resin composition R24 containing the wax composition W10 had an excessive amount of dialkylketone B in the wax composition W10, resulting in a high rate of change in the dynamic friction coefficient before and after the cycle test of 11.2%, and poor stability of the frictional force against temperature changes. In Comparative Example 7, the resin composition R25 containing the wax composition W11 showed poor stability of frictional force against temperature changes, with a high rate of change of 15.7% in the dynamic friction coefficient before and after the cycle test, because the number of carbon atoms in the secondary alcohol and dialkyl ketone contained in the wax composition W11 was too small. In Comparative Example 8, the resin composition R26 containing the wax composition W12 had excessive friction and insufficient lubricity because the secondary alcohol and dialkyl ketone contained in the wax composition W12 had too many carbon atoms. The rate of change in the dynamic friction coefficient before and after the cycle test was high at 12.6%, and the stability of the frictional force against temperature changes was poor. In contrast, the resin compositions R14 to R22 of Examples 10 to 18 contained one of the wax compositions W1 to W8 of the present invention. As a result, the resin films formed using resin compositions R14 to R22 had a dynamic friction coefficient (μ) of less than 0.250, and the rate of change when comparing the dynamic friction coefficient (μ) before and after the cycle test was low, less than 10.0%. Therefore, it was shown that resin compositions R14 to R22, by containing the wax composition of the present invention, are imparted with a frictional force exhibiting good slipperiness, and furthermore, possess a frictional force that is stable against temperature changes.

[0075] <Example 19: Production of Emulsion> An emulsion (cosmetic) was obtained by mixing each component according to the composition shown in Table 6 below.

[0076] [Table 6]

[0077] <Example 20: Cream Production> A cream (cosmetic) was obtained by mixing the components according to the composition shown in Table 7 below.

[0078] [Table 7]

[0079] <Example 21: Manufacturing of sunscreen> A sunscreen (cosmetic) was obtained by mixing each component according to the composition shown in Table 8 below.

[0080] [Table 8]

[0081] <Example 22: Manufacturing of point makeup remover> A point makeup remover (cosmetic) was obtained by mixing each component according to the composition shown in Table 9 below.

[0082] [Table 9]

[0083] <Example 23: Manufacturing of cleansing oil> A cleansing oil (cosmetic) was obtained by mixing each component according to the composition shown in Table 10 below.

[0084] [Table 10]

[0085] <Example 24: Manufacturing of hair oil> Hair oil (cosmetic product) was obtained by mixing each component according to the composition shown in Table 11 below.

[0086] [Table 11]

[0087] <Example 25: Manufacturing of Treatment> A treatment (cosmetic) was obtained by mixing each component according to the composition shown in Table 12 below.

[0088] [Table 12]

[0089] <Example 26: Mascara Manufacturing> Mascara (cosmetic product) was obtained by mixing each component according to the composition shown in Table 13 below.

[0090] [Table 13]

[0091] <Example 27: Manufacturing of Liquid Foundation> A liquid foundation (cosmetic) was obtained by mixing each component according to the composition shown in Table 14 below.

[0092] [Table 14]

[0093] <Example 28: Manufacturing of lipstick> Lipstick (cosmetic) was obtained by mixing each component according to the composition shown in Table 15 below.

[0094] [Table 15] [Industrial applicability]

[0095] The wax composition of the present invention can impart a stable frictional force to oils and resins in response to temperature changes, thereby enabling them to exhibit consistent performance even in environmental changes such as from summer to winter. By providing a stable frictional force in response to temperature changes, the wax composition of the present invention can, for example, impart a stable thickness to oily cosmetics, provide stable slipperiness to resins, and provide stable lubrication to lubricating oils. Therefore, the wax composition of the present invention is useful in various fields that use oils or resins, such as cosmetics, resins, and lubricating oils.

Claims

[Claim 1] A wax composition comprising a secondary alcohol A having 11 to 61 carbon atoms and a dialkylketone B having 11 to 61 carbon atoms, wherein the mass ratio of the secondary alcohol A to the dialkylketone B (secondary alcohol A:dialkylketone B) is 70:30 to 99.9:0.1.

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