JP2015071545A - Oleaginous base, and cosmetic and external preparation using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an oleaginous base having high hydratability, and a cosmetic and an external preparation using the same.SOLUTION: An oleaginous base containing a mixed ester compound of pyroglutamic acid, at least one selected from univalent fatty acid and N-acylated amino acid, and dimer diol has a structure of the general formula (I). (In the formula, R is at least one residue selected from the univalent fatty acid and the N-acylated amino acid used in esterification reaction, and a, b, c and d are an integer of 1 or more where a+b+c+d=12 to 40. In addition, a portion of a pyroglutamic acid group and an RCO group becomes a hydroxyl group depending on the esterification degree.)

Description

  The present invention relates to an oily base and cosmetics and external preparations using the same.

  Conventionally, oily raw materials containing various ester compounds, that is, oily bases, have been used in cosmetics and external preparations. Among them, N-long-chain acylamino acids and dicarboxylic acids such as dimer acids react with sterols and have water-holding properties. By blending them into cosmetics and external preparations, they give hair and skin repair and moisturizing effects. It is known (see Patent Documents 1 and 2). Moreover, it is known that the ester compound of dimer diol and a fatty acid is excellent in safety, stability, gloss, and feeling of use (see Patent Document 3). Furthermore, an oligomer ester composed of dimer acid and dimer diol and sterol Ester compounds, ester compounds of pyroglutamic acid and higher alcohols or polyhydric alcohols, and the like have been used as water-hydrating oils for cosmetics (see Patent Documents 4 and 5).

  However, these ester compounds are still insufficient in terms of water-holding performance when considered as an oily base for cosmetics and external preparations that complement the decrease in skin moisturizing function. Also, conventionally, it is essential to have a sterol group in the structure in order to obtain a large water holding performance, but for sterols, it has difficulty in handling such as peroxide value and color tone management. Therefore, an oily base having a high water holding performance without a sterol skeleton has been desired.

Japanese Patent Laid-Open No. 03-275697 JP 2001-199937 A JP 2001-072530 A JP 2004-256515 A JP 2007-099656 A

  An object of the present invention is to provide an oily base having a high water-holding property, and a cosmetic and an external preparation using the same.

The present invention is an oily substance comprising a mixed ester compound of dimerdiol with at least one selected from pyroglutamic acid, monovalent fatty acid and N-acylated amino acid having the structure of the following general formula (I): It is a base.

(I)
Wherein R is at least one residue selected from the monovalent fatty acid and N-acylated amino acid used in the esterification reaction, and a, b, c and d are integers of 1 or more and a + b + c + d = (In addition, depending on the degree of esterification, a part of pyroglutamic acid group and RCO group is a hydroxyl group.)

  Moreover, it is preferable that the water-holding power of the oil-based base is 300% or more.

  In the oil base, the monovalent fatty acid is preferably a linear fatty acid having 8 to 26 carbon atoms.

  In the oil base, the monovalent fatty acid is preferably a branched fatty acid having 4 to 22 carbon atoms.

  In the oily base, the amino acid portion of the N-acylated amino acid is preferably selected from N-methylglycine or N-methyl-β-alanine.

  Moreover, this invention is the cosmetics containing the said oil-based base.

  Moreover, this invention is an external preparation containing the said oil-based base.

  In the present invention, it is possible to provide an oily base having a high water-holding property, and a cosmetic and an external preparation using the same.

It is a figure which shows the result of having conducted the water-holding power test using the diester obtained in Examples 1-12, and the ester obtained in Comparative Examples 1-6. It is a figure which shows the viscosity (mPa * s) in 25 degreeC of the oil-based base containing the diester obtained in Examples 1-4.

  Embodiments of the present invention will be described below. This embodiment is an example for carrying out the present invention, and the present invention is not limited to this embodiment.

  As a result of intensive studies, the present inventors have found that a mixed ester compound of pyroglutamic acid, at least one selected from monovalent fatty acids and N-acylated amino acids, and dimer diol has a conventional sterol as a skeleton. It has been found that it has a water holding performance greatly surpassing that of the ester compound. In addition, this mixed ester compound has a lower viscosity than a single ester compound with pyroglutamic acid, and is excellent in safety, stability, gloss, and feeling of use while adjusting to a base property suitable for the application. It has been found that cosmetics and external preparations containing a base can also be made excellent in performance and functionality.

  The water-holding property refers to the performance of an oil-soluble substance that entraps water as seen in lanolin, and can be used as an index of moisture retention performance and emulsion stability.

  The oily base according to an embodiment of the present invention contains a mixed ester compound of pyroglutamic acid, at least one selected from monovalent fatty acids and N-acylated amino acids, and dimer diol. This mixed ester compound has a structure represented by the following general formula (I).

(I)
Wherein R is at least one residue selected from the monovalent fatty acid and N-acylated amino acid used in the esterification reaction, and a, b, c and d are integers of 1 or more and a + b + c + d = (In addition, depending on the degree of esterification, a part of pyroglutamic acid group and RCO group is a hydroxyl group.)

  A mixed ester compound of pyroglutamic acid having a structure represented by the above general formula (I), at least one selected from monovalent fatty acids and N-acylated amino acids, and dimer diol is a monoester or a diester. And at least one of a mixture of monoesters and diesters. The composition ratio in the case of a mixture is not particularly limited.

  In the present embodiment, the oily base functions as an amphiphilic oil that can adjust the emollient effect such as softening action, protective action, moisture evaporation inhibiting action, etc. on the skin, and the physical properties of the surfactant to be blended. It is a fat-soluble component that is widely used in creams, emulsions, and the like having functions such as improvement of the skin and cleansing action. In addition, it is blended in products such as foundations and lipsticks for the purpose of improving the cosmetic effect by improving pigment dispersion and appearance, and imparting pigments to the skin. Furthermore, in hair care cosmetics, it has a role of imparting luster and setability to hair, and is used as a base for cosmetics, external preparations, etc. in accordance with the intended use.

  The mixed ester compound of pyroglutamic acid according to the present embodiment, at least one selected from monovalent fatty acids and N-acylated amino acids, and dimer diol is pyroglutamic acid obtained by causing intramolecular condensation reaction of glutamic acid. It can be obtained by esterifying a mixture of a monovalent fatty acid and an N-acylated amino acid and a dimer diol obtained by hydrogenating a dimer acid obtained by dimerizing an unsaturated fatty acid.

  It is known that pyroglutamic acid used in the present embodiment has a moisture regulating function from the viewpoint of increasing the moisture content of the stratum corneum of skin even at low atmospheric humidity. And since it is a component of a natural moisturizing factor, it is one of the most known humectants for personal care applications.

  An ester compound containing an amino skeleton derived from an amino acid such as pyroglutamic acid in the molecule is said to have physical properties different from those of ordinary fatty acid esters. The difference in physical properties is expected to be attributed to the hydrophilicity imparted by the amino group it has, and the performance varies greatly depending on the type of compound to be esterified. For the mixed ester compound of pyroglutamic acid, at least one selected from monovalent fatty acid and N-acylated amino acid, and dimer diol, dimer diol is selected as the optimum esterification target, and the structure In particular, it is an oily base imparted with high water retention performance while being greatly differentiated from conventional compounds.

  Although there is no restriction | limiting in particular as a monovalent fatty acid used in this embodiment, Usually, as long as it is used for cosmetics etc., any thing can be used. As the monovalent fatty acid, a linear fatty acid having 8 to 26 carbon atoms or a branched fatty acid having 4 to 22 carbon atoms is preferable, a linear fatty acid having 10 to 22 carbon atoms, or 8 to 8 carbon atoms. Twenty branched fatty acids are more preferred.

  Specifically, as a linear fatty acid having 8 to 26 carbon atoms, more preferably 10 to 22 carbon atoms, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behen Examples include linear saturated fatty acids such as acids and coconut oil fatty acids, and linear unsaturated fatty acids such as palmitoleic acid, oleic acid, linoleic acid, linolenic acid, and elaidic acid, and also have 4 to 22 carbon atoms, more preferably 8 to Examples of the 20 branched fatty acids include branched fatty acids such as 2-ethylhexanoic acid, isononanoic acid, isopalmitic acid, isostearic acid, isoarachidic acid, and lanolin fatty acid.

  The acyl group of the N-acylated amino acid used in the present embodiment is preferably an alkanoyl group, and the carbon number thereof is 4 to 26, preferably 8 to 22, and more preferably 10 to 18. For example, straight-chain saturated fatty acids such as hexanoic acid, caproic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, coconut oil fatty acid, oleic acid, linoleic acid, linolenic acid, elaidic acid, etc. Examples include those derived from branched chain fatty acids such as chain unsaturated fatty acids, isobutanoic acid, 2-ethylhexanoic acid, isononanoic acid, isopalmitic acid, isostearic acid, isoarachidic acid, and lanolin fatty acid.

  The type of amino acid in the amino acid portion of the N-acylated amino acid is not particularly limited, but preferred examples include glycine, alanine, threonine, β-alanine, N-methylglycine (sarcosine), N-methyl-β. -Alanine, aminobutyric acid, glutamic acid, aspartic acid and the like can be mentioned, and N-methylglycine or N-methyl-β-alanine is preferable from the viewpoint of being a monovalent amino acid.

  One or more of these monovalent fatty acids and N-acylated amino acids can be used.

  The dimer diol used in the present embodiment is one in which the carboxyl group portion of dimer acid is a hydroxyl group. For example, dimer acid or a lower alcohol ester thereof is preferably hydrogenated in the presence of a catalyst so that the carboxyl group portion of dimer acid is a hydroxyl group. Dimer acid is a dibasic acid obtained by an intermolecular polymerization reaction of an unsaturated fatty acid. In general, a compound obtained by dimerizing an unsaturated fatty acid having 11 to 22 carbon atoms with a clay catalyst or the like is preferable. Examples of unsaturated fatty acids to be dimerized include myristoleic acid, palmitoleic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, erucic acid, linoleic acid, linolenic acid, arachidonic acid, and the like. The acid can be reduced to a saturated aliphatic dibasic acid by reduction of double bonds existing in the dimer acid residue by hydrogenation reduction. Examples of the lower alcohol ester of dimer acid include esters derived from alcohol having 1 to 6 carbon atoms, preferably 2 to 4 carbon atoms. The dimer diol is usually a diol having 22 to 44 carbon atoms, preferably 24 to 40 carbon atoms, more preferably about 36 carbon atoms as a main component. The dimer diol obtained industrially may contain, for example, a trimer triol, a monomer alcohol and an ether compound depending on the degree of purification of the dimer acid used as a raw material and its lower alcohol ester, and generally contains dimer diol. Since those having an amount of 70 to 100% by weight and those having a dimer diol content of 90 to 100% by weight after further purification have been distributed, these can be used. Any of them can be used in the present embodiment. As dimer diol, those derived from animal fats and oils and vegetable fats and oils are distributed, but those derived from vegetable fats and oils are desirable. As such a dimer diol, PRIDOL 2033 by Claude Japan, Sovermol 908 by Cognis Japan, etc. can be obtained as a commercial item, for example.

  The mixed ester compound of pyroglutamic acid according to the present embodiment, at least one selected from monovalent fatty acids and N-acylated amino acids, and dimer diol, for example, dimer diol, the aforementioned pyroglutamic acid, and monovalent It is obtained by esterification or transesterification with at least one selected from the following fatty acids and N-acylated amino acids. The conditions for the esterification reaction are not particularly limited, and are carried out by a generally used method. For example, esterification may be performed at a reaction temperature of 50 to 200 ° C. using paratoluenesulfonic acid, sulfuric acid, hydrochloric acid, methanesulfonic acid, hydrogen fluoride, or the like as a catalyst and benzene, toluene, xylene, or the like as a solvent. it can. Alternatively, esterification can be carried out at a reaction temperature of 100 to 200 ° C. with no catalyst and no solvent. In the transesterification, an alkali catalyst such as sodium hydroxide, potassium hydroxide or potassium carbonate, a metal alkoxide such as sodium methoxide, or the like can be used as a catalyst.

  The mixed ester compound of pyroglutamic acid according to this embodiment, at least one selected from monovalent fatty acids and N-acylated amino acids, and dimer diol, by appropriately selecting the raw material and the degree of esterification, Viscosity, state (solid, soft wax, liquid, etc.), IOB value, compatibility with other components (compatibility, etc.), etc. can be adjusted arbitrarily, providing cosmetics with excellent usability, stability, etc. can do. This mixed ester compound can be produced, for example, as follows.

  Dimerdiol, pyroglutamic acid, and at least one selected from monovalent fatty acids and N-acylated amino acids are charged. Preferably, for example, p-toluenesulfonic acid is added as a catalyst, for example, 0.5% by weight of the charged amount. Then, the temperature is raised to, for example, 150 ° C. while allowing nitrogen to flow. Sampling is performed after the reaction time has elapsed, and the ester reaction is terminated at a predetermined acid value. Water-cooled, neutralized with 20% aqueous sodium hydroxide at 70 ° C. to 80 ° C., dehydrated and purified, and then pre-coated to obtain an ester compound.

  The IOB value of the mixed ester compound according to this embodiment is desirably 1.0 or less. The IOB (Inorganic Organic Balance) is a ratio of the inorganic value (IV) to the organic value (OV) obtained based on the organic conceptual diagram, that is, “inorganic value (IV) / organic value (OV)”. = IOB ". This is explained in “Organic Conceptual Diagram-Basics and Applications” (Yoshio Koda, Sankyo Publishing, 1984).

  The viscosity of the mixed ester compound according to this embodiment is preferably 10000 mPa · s or less, more preferably in the range of 100 to 5000 mPa · s, when it is liquid. When the viscosity exceeds 10,000 mPa · s, it becomes difficult to blend in cosmetics or external preparations. However, this is not the case when the compound is a paste-like compound.

  The water-holding power of the mixed ester compound according to the present embodiment is 300% or more because the water-holding power of lanolin, which is widely used as a natural water-holding oil in cosmetics and external preparations, is 250 to 300%. Is preferable, and about 1000% is more preferable. If the water retention capacity is less than 300%, the skin moisturizing function may be inferior when blended with cosmetics or external preparations.

  In the mixed ester compound according to the present embodiment, by selecting and adjusting the blending ratio of monovalent fatty acids and the type of N-acylated amino acid, it can flow even when stored in a low temperature environment such as a −5 ° C. environment. And an oily base having excellent low-temperature characteristics that can maintain the property and transparency of the liquid.

  The mixed ester compound according to the present embodiment is used as an oily base for cosmetics and external preparations. That is, cleansing oil, cleansing liquid, cleansing foam, cleansing cream, cleansing milk, cleansing gel, cleansing sheet, massage cream, massage milk, cold cream, emollient cream, emollient milk, moisture cream , Moisture emulsion, hand cream, hand emulsion, cream foundation, liquid foundation, cake foundation, press powder, moisture lotion, astringent lotion, peel off pack, mud pack, lipstick, eye shadow, tic, hair liquid, hair pomade, hair cream , Hair lotion, hair mousse, set lotion, hair shampoo, rinse-in shampoo, body Shampoo, hair rinse, hair conditioner, hair treatment, solid detergent, liquid detergent, antiperspirant, after shave cream, sunscreen cream, sunscreen lotion, sunscreen oil, hair restorer, hair nourishing agent, bath preparation, topical pharmaceutical composition, etc. It can be used as an oily base in the preparation of cosmetics and external preparations. There are no particular restrictions on the dosage form of cosmetics and external preparations, and any agent such as an emulsifying system, solution system, solubilizing system, powder dispersion system, water-oil two-layer system, water-oil-powder three-layer system, etc. It may be in shape.

  The blending amount of the mixed ester compound in the cosmetic and the external preparation is not particularly limited, but is preferably 0.01 to 60% by weight, for example, 0.1 to 20% by weight based on the total amount of the cosmetic or the external preparation. % Is more preferable.

  In addition to the oily base according to the present embodiment, the cosmetic and external preparation according to the embodiment of the present invention may be blended with other oily bases. Examples of such an oily base include: Petroleum and mineral-derived raw materials such as liquid paraffin, solid paraffin, petrolatum, microcrystalline wax, ceresin, polyisobutene, synthetic wax such as wood wax, candelilla wax, carnauba wax, whale wax, beeswax, animal and plant wax, jojoba oil, olive oil , Castor oil, macadamia nut oil, sesame oil, cacao oil, mink oil, isopropyl myristate, cetyl octanoate, octyldodecyl myristate, glyceryl trioctanoate, tri (caprylic acid, capric acid) glycerin, and animal and vegetable oils and fats, cetyl alcohol , Stearyl alcohol, behenyl alcohol, Synthesis of yl alcohol, hexadecyl alcohol, isostearyl alcohol, octyldodecyl alcohol, and higher alcohols derived from animals and plants, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, ricinoleic acid, Synthetic and animal and plant-derived higher fatty acids such as hydroxystearic acid, isostearic acid, and isopalmitic acid, octyldodecyl pyrrolidonecarboxylate, dihexyldecyl lauroylglutamate, dioctyldecyl lauroylglutamate, dicetyl lauroylglutamate, dilauroylglutamate (phytosteryl / octyldodecyl) Synthesis and amino acids from myristoylmethylaminopropionate hexyldecyl, lauroyl sarcosine isopropyl, etc. Oil phase raw material, methylpolysiloxane, polyoxyethylene / methylpolysiloxane, polyoxypropylene / methylpolysiloxane, poly (polyoxyethylene / polyoxypropylene) methylpolysiloxane, methylphenylpolysiloxane, fatty acid-modified polysiloxane, aliphatic Examples thereof include those usually used as oil components such as silicones such as silicone polymers such as alcohol-modified polysiloxane and amino acid-modified polysiloxane, and resin acids, esters, and ketones.

  These other oily bases can be optionally used in combination as long as the effects of the oily base according to the present embodiment are not impaired. In the cosmetic and the external preparation according to this embodiment, the other oily base is blended in an amount of, for example, 0.1 to 80% by weight, preferably 1 to 50% by weight, based on the total oily base.

  In the cosmetic and the external preparation according to this embodiment, a surfactant may be used in combination as long as the effect of the oil base according to this embodiment is not inhibited. Surfactants include N-long chain acyl acidic amino acid salts and N-long chain acyl neutral amino acid salts, such as N-long chain acyl amino acid salts, N-long chain fatty acid acyl-N-methyl taurine salts, alkyl sulfates, and the like. Alkylene oxide adducts, fatty acid amide ether sulfates, fatty acid metal salts and weak bases, sulfosuccinic acid surfactants, alkyl phosphates and their alkylene oxide adducts, anionic surfactants such as alkyl ether carboxylic acids, higher alcohols and their Ether type nonionic surfactant such as alkylene oxide adduct, glycerin ester, sorbitan ester, ether ester type nonionic surfactant such as alkylene oxide adduct, polyoxyalkylene fatty acid ester, glycerin ester, fatty acid polyglyceride Esters, N-long chain acyl peptide polyglycerol, sorbitan ester, sucrose fatty acid ester, and other ester type surfactants, alkyl glucosides, hydrogenated castor oil isostearic acid pyroglutamic acid diester and its ethylene oxide adduct, and fatty acid alkanolamide Nitrogen-containing nonionic surfactants, aliphatic amine salts such as alkylammonium chloride and dialkylammonium chloride, quaternary ammonium salts thereof, aromatic quaternary ammonium salts such as benzalkonium, and cations such as fatty acid acylarginine esters Examples thereof include various surfactants such as surfactants, betaine-type surfactants such as carboxybetaine, aminocarboxylic acid-type surfactants, and imidazoline-type amphoteric surfactants.

  The compounding quantity of surfactant is 0.1 to 60 weight% with respect to the whole quantity of cosmetics and an external preparation, Preferably it is 0.5 to 20 weight%.

  You may mix | blend the moisturizer of a water phase component with the cosmetics and external preparation which concern on this embodiment. As humectants, amino acids such as glycine, alanine, serine, threonine, arginine, glutamic acid, aspartic acid, leucine, valine, ethylene glycol, propylene glycol, 1,3-butylene glycol, dipropylene glycol, glycerin, sorbitol, xylitol Polyalcohols such as polyglutamic acid, polyaspartic acid and salts thereof, polyethylene glycol, gum arabic, alginate, xanthan gum, hyaluronic acid, hyaluronate, chitin, water-soluble chitin, carboxyvinyl polymer, carboxy Methylcellulose, hydroxyethylcellulose, hydroxypropyltrimethylammonium chloride, polydimethylmethylenepiperidinium chloride, polyvinylpyrrolidone Conductors, quaternary ammonium, cationized proteins, collagen degradation products and derivatives thereof, acylated proteins, water-soluble polymers such as polyglycerol, amino acid polyglycerol esters, sugar alcohols such as mannitol and alkylene oxide adducts thereof, and ethanol And lower alcohols such as propanol.

  The amount of the humectant is, for example, 0.1 to 60% by weight, preferably 0.5 to 20% by weight, based on the total amount of the cosmetic and the external preparation.

  You may mix | blend antiseptic | preservative, a disinfectant, a chelating agent, a pH adjuster, a ultraviolet absorber, a whitening agent etc. in the cosmetics and external preparation which concern on this embodiment.

  Examples of the preservative include phenols, benzoic acid and salts thereof, halogenated bisphenols, acid amides, quaternary ammonium salts and the like.

  Examples of the disinfectant include trichlorocarbanyl, zinc pyridione, benzalkonium chloride, chlorhexidine, halocarban, hinokitiol, phenol, isopropylphenol, and photosensitizers.

  Examples of chelating agents include edetate and sodium oxalate.

  Examples of the pH adjuster include citric acid, succinic acid, hydrochloric acid, ethanolamine, diethanolamine, triethanolamine, aqueous ammonia, sodium hydroxide, sodium chloride and the like.

  Examples of ultraviolet absorbers include benzophenone derivatives, paraaminobenzoic acid derivatives, paramethoxycinnamic acid derivatives, salicylic acid derivatives, dimethoxybenzylidenedioxoimidazolidinepropionate octyl, urocanic acid, ethyl urocanate, 4-tert-butyl-4'-methoxy Examples include dibenzoylmethane, methyl anthranilate, rutin and derivatives thereof.

  Examples of the whitening agent include kojic acid, arbutin, ascorbic acid, ascorbic acid glucoside, glutathione, ellagic acid, placenta extract, oryzanol, and lucinol.

  Furthermore, you may mix | blend the component according to the cosmetics and external preparation made into the cosmetics and external preparation which concern on this embodiment. Examples of such components include a fragrance, a pigment, a pearling agent, an anti-inflammatory agent, an analgesic, an antifungal agent, a hair restorer, an antiperspirant, a vitamin agent, a hormonal agent, a viscosity modifier, and a crude drug.

  Hereinafter, although an example and a comparative example are given and the present invention is explained more concretely in detail, the present invention is not limited to the following examples. In the examples, unless otherwise specified, “part” represents “part by mass” and “%” represents “% by mass”.

<Example 1: Synthesis of dipyroglutamic acid [2 mol] dimer diol [1 mol] ester>
Dimer diol (Compound name: Dimer linoleyl alcohol “Pripol 2033”, manufactured by Croda Japan Co., Ltd. In Examples 1 to 12 and Comparative Examples 1 to 3, this product was used as a dimer diol for synthesis) 1136 parts, pyro 464 parts of glutamic acid are charged and stirred, and the reaction is carried out by raising the temperature to 190 ° C. while introducing nitrogen. Sampling was performed after 7 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-filtered to obtain 1473.2 parts of the product (yield 92.1%). The obtained diester compound was a slightly yellow viscous liquid having a viscosity at 25 ° C. of 32160 mPa · s.

  As a result of analysis of this product, it was a compound having an acid value of 3.97, a saponification value of 144.63 (theoretical value = 147.9), and an IOB value of 0.60. The acid value and saponification value were measured by the quasi-drug raw material standard 2006 general test method.

About this ester compound, as a result of measuring an infrared absorption spectrum using an infrared absorption spectrum measuring apparatus (manufactured by Shimadzu Corporation, IRPestige-21), wavelengths of 3232.83 cm ⁻¹ (hydroxyl group), 1741.80 cm ⁻¹ (ester) ) And 1709.00 cm ⁻¹ (amide), characteristic absorption was observed.

<Example 2: Synthesis of di (pyroglutamic acid [1.5 mol] / isostearic acid [0.5 mol]) dimer diol [1 mol] ester>
Charge 922.5 parts of dimer diol, 333 parts of pyroglutamic acid and 244.5 parts of isostearic acid, stir, add 7.5 parts of paratoluenesulfonic acid, raise the temperature to 150 ° C. while allowing nitrogen to flow, and react. . Sampling was performed after 8 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-filtered to obtain 1301.9 parts of the product (yield 86.8%). The obtained diester compound was a pale yellow liquid having a viscosity at 25 ° C. of 8130 mPa · s.

  As a result of analysis of this product, it was a compound having an acid value = 5.38, a saponification value = 162.45 (theoretical value = 134.1), and an IOB value = 0.43.

As a result of carrying out an infrared absorption spectrum measurement about this ester compound, characteristic absorption was recognized by wavelength 3224.15cm < ^-1 > (hydroxyl group), 1738.90cm < ^-1 > (ester), and 1709.00cm < ^-1 > (amide | amido).

Example 3: Synthesis of di (pyroglutamic acid [1 mol] / isostearic acid [1 mol]) dimer diol [1 mol] ester
849 parts of dimer diol, 450 parts of pyroglutamic acid and 201 parts of isostearic acid are charged, stirred, 7.5 parts of paratoluenesulfonic acid is added, and the temperature is raised to 150 ° C. while allowing nitrogen to flow. Sampling was performed after 8 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-filtered to obtain 1311.7 parts of the product (yield 87.4%). The obtained diester compound was a pale yellow liquid having a viscosity at 25 ° C. of 1990 mPa · s.

  As a result of analysis of this product, it was a compound having an acid value = 3.42, a saponification value = 125.43 (theoretical value = 122.7), and an IOB value = 0.29.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 3218.37 cm ⁻¹ (hydroxyl group), 1738.90 cm ⁻¹ (ester) and 1710.93 cm ⁻¹ (amide).

<Example 4: Synthesis of di (pyroglutamic acid [0.5 mol] / isostearic acid [1.5 mol]) dimer diol [1 mol] ester>
783 parts of dimer diol, 622.5 parts of pyroglutamic acid and 94.5 parts of isostearic acid are added, stirred, 7.5 parts of paratoluenesulfonic acid is added, and the temperature is raised to 150 ° C. while allowing nitrogen to flow. . Sampling was performed after 8 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-coated to obtain 1321.4 parts (yield 88.1%) of the product. The obtained diester compound was a pale yellow liquid having a viscosity at 25 ° C. of 740 mPa · s.

  As a result of analysis of this product, it was a compound having an acid value = 2.2, a saponification value = 115.16 (theoretical value = 113.1), and an IOB value = 0.18.

As a result of measuring the infrared absorption spectrum of the ester compound, characteristic absorption was observed at wavelengths of 3219.33 cm ⁻¹ (hydroxyl group), 1738.90 cm ⁻¹ (ester) and 1712.86 cm ⁻¹ (amide).

<Example 5: Synthesis of di (pyroglutamic acid [1 mol] / N-myristoyl-N-methyl-β-alanine [1 mol]) dimer diol [1 mol] ester>
837 parts of dimer diol, 472.5 parts of pyroglutamic acid, 190.5 parts of N-myristoyl-N-methyl-β-alanine were added, stirred, 7.5 parts of paratoluenesulfonic acid was added, and nitrogen was introduced. The temperature is raised to 150 ° C. to react. Sampling was performed after 8 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-filtered to obtain 1303.1 parts of the product (yield 86.9%). The obtained diester compound was a pale yellow liquid having a viscosity at 25 ° C. of 3170 mPa · s.

  As a result of analysis, the product was a compound having an acid value of 9.71, a saponification value of 118.84 (theoretical value = 119), and an IOB value of 0.46.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 3251.16 cm ⁻¹ (hydroxyl group), 1736.97 cm ⁻¹ (ester) and 1652.10 cm ⁻¹ (amide).

<Example 6: Synthesis of di (pyroglutamic acid [1 mol] / N-lauroyl sarcosine [1 mol]) dimer diol [1 mol] ester>
573 parts of dimer diol, 289 parts of pyroglutamic acid and 138 parts of N-lauroylsarcosine are charged, stirred, 5 parts of paratoluenesulfonic acid is added, and the temperature is raised to 150 ° C. while introducing nitrogen, and the reaction is carried out. Sampling was performed after 8 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-filtered to obtain 796 parts of the product (yield 79.6%). The obtained diester compound was a pale yellow liquid having a viscosity at 25 ° C. of 4440 mPa · s.

  As a result of analysis of this product, it was a compound having an acid value of 6.15, a saponification value of 114.94 (theoretical value = 125), and an IOB value of 0.48.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 3259.84 cm ⁻¹ (hydroxyl group), 1746.62 cm ⁻¹ (ester) and 1661.75 cm ⁻¹ (amide).

<Example 7: Synthesis of di (pyroglutamic acid [1 mol] / isostearic acid [0.5 mol] / lauroyl sarcosine [0.5 mol]) dimer diol [1 mol] ester>
Dimer diol 853.5 parts, pyroglutamic acid 205.5 parts, isostearic acid 226.5 parts, lauroyl sarcosine 214.5 parts are charged and stirred, while paratoluenesulfonic acid 7.5 parts are added and nitrogen is introduced. The temperature is raised to 150 ° C. to react. Sampling was performed after 8 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-filtered to obtain 1188 parts (yield 79.2%). The obtained diester compound was a pale yellow liquid having a viscosity at 25 ° C. of 2910 mPa · s.

  As a result of analysis of this product, it was a compound having an acid value of 12.71, a saponification value of 128.63 (theoretical value = 113.6), and an IOB value = 0.38.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 3247.30 cm ⁻¹ (hydroxyl group), 1740.83 cm ⁻¹ (ester) and 1709.97 cm ⁻¹ (amide).

<Example 8: Synthesis of di (pyroglutamic acid [1 mol] / caprylic acid [1 mol]) dimer diol [1 mol] ester>
663 parts of dimer diol, 178 parts of pyroglutamic acid and 159 parts of caprylic acid are charged, stirred, 5 parts of paratoluenesulfonic acid is added, and the temperature is raised to 150 ° C. while flowing in nitrogen, and the reaction is carried out. Sampling was performed after 8 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-coated to obtain 790 parts of the product (yield 79.0%). The obtained diester compound was a pale yellow liquid having a viscosity at 25 ° C. of 1700 mPa · s.

  As a result of analysis of this product, it was a compound having an acid value = 2.86, a saponification value = 147.94 (theoretical value = 145), and an IOB value = 0.35.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 3321.87 cm ⁻¹ (hydroxyl group), 1738.90 cm ⁻¹ (ester) and 1709.00 cm ⁻¹ (amide).

<Example 9: Synthesis of di (pyroglutamic acid [1 mol] / behenic acid [1 mol]) dimer diol [1 mol] ester>
Charge 320.4 parts of dimer diol, 76.8 parts of pyroglutamic acid and 202.8 parts of behenic acid, stir, add 3 parts of paratoluenesulfonic acid, raise the temperature to 150 ° C. while allowing nitrogen to flow, and react. . Sampling was performed after 8 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-filtered to obtain 463 parts of the product (yield 77.2%). The obtained diester compound was a pale yellow solid.

  As a result of analysis of this product, it was a compound having an acid value = 3.42, a saponification value = 1117.99 (theoretical value = 115.7), and an IOB value = 0.27.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 3218.37 cm ⁻¹ (hydroxyl group), 1738.90 cm ⁻¹ (ester) and 1712.86 cm ⁻¹ (amide).

<Example 10: Synthesis of di (pyroglutamic acid [1 mol] / oleic acid [1 mol]) dimer diol [1 mol] ester>
849 parts of dimer diol, 204 parts of pyroglutamic acid, and 447 parts of oleic acid are charged, stirred, 7.5 parts of paratoluenesulfonic acid is added, and the temperature is raised to 150 ° C. while allowing nitrogen to flow. Sampling was performed after 7 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-filtered to obtain 1177.5 parts (yield 78.5%). The obtained diester compound was a slightly yellow liquid with a viscosity at 25 ° C. of 1400 mPa · s.

  As a result of analysis, the product was a compound having an acid value = 5.57, a saponification value = 133.41 (theoretical value = 123), and an IOB value = 0.29.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths 3218.37 cm ⁻¹ (hydroxyl group), 1738.90 cm ⁻¹ (ester) and 1712.85 cm ⁻¹ (amide).

<Example 11: Synthesis of sesqui [pyroglutamic acid [0.75 mol] / isostearic acid [0.75 mol]) dimer diol [1 mol] ester>
951 parts of dimer diol, 378 parts of pyroglutamic acid and 171 parts of isostearic acid are charged, stirred, 7.5 parts of paratoluenesulfonic acid is added, and the temperature is raised to 150 ° C. while allowing nitrogen to flow, and the reaction is carried out. Sampling was conducted after 6 hours and 30 minutes of reaction time, and the ester reaction was completed at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-coated to obtain 1324 parts of the product (yield 88.3%). The obtained sesquiester compound was a pale yellow liquid with a viscosity at 25 ° C. of 1920 mPa · s.

  As a result of analysis of this product, acid value = 0.65, saponification value = 107.47 (theoretical value = 99.4), hydroxyl value = 43 (theoretical value = 33.1), IOB value = 0.29. It was this compound.

As a result of carrying out an infrared absorption spectrum measurement about this ester compound, characteristic absorption was recognized in wavelength 3232.83 cm < ^-1 > (hydroxyl group), 1738.90 cm < ^-1 > (ester), and 1709.00 cm < ^-1 > (amide | amido).

<Example 12: Synthesis of mono (pyroglutamic acid [0.5 mol] / isostearic acid [0.5 mol]) dimer diol [1 mol] ester>
1299.6 parts of dimer diol, 156.6 parts of pyroglutamic acid and 343.8 parts of isostearic acid are charged, stirred, 9 parts of paratoluenesulfonic acid is added, and the temperature is raised to 150 ° C. while allowing nitrogen to flow. . Sampling was performed after 5 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-filtered to obtain 1467 parts of the product (yield 81.5%). The obtained monoester compound was a pale yellow liquid having a viscosity at 25 ° C. of 1710 mPa · s.

  As a result of analysis of this product, it was a compound having an acid value = 0.44, a saponification value = 81.71 (theoretical value = 77.3), and an IOB value = 0.29.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 3364.00 cm ⁻¹ (hydroxyl group), 1738.90 cm ⁻¹ (ester) and 1703.23 cm ⁻¹ (amide).

  The synthesis example about the compound of the comparative example used for the comparison with the compound of an Example is shown below.

<Comparative Example 1: Synthesis of diisostearic acid [2 mol] dimer diol [1 mol] ester>
Charge 433.8 parts of dimer diol and 466.2 parts of isostearic acid, stir and react by raising the temperature to 250 ° C. while flowing nitrogen. Sampling was performed after 7 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-coated to obtain 835 parts (yield 92.8%) of the product. The obtained diester compound was a pale yellow liquid having a viscosity at 25 ° C. of 370 mPa · s.

  As a result of analysis, the product was a compound having an acid value = 4.33, a saponification value = 104.28 (theoretical value = 104.9), and an IOB value = 0.09.

As a result of carrying out an infrared absorption spectrum measurement about this ester compound, characteristic absorption was recognized by the wavelength 3231.76cm < ^-1 > (hydroxyl group) and 1739.87cm < ^-1 > (ester).

<Comparative Example 2: Synthesis of monoisostearic acid [1 mol] dimer diol [1 mol] ester>
A dimer diol (585.9 parts) and isostearic acid (314.1 parts) are charged, stirred, and reacted by raising the temperature to 230 ° C. while introducing nitrogen. Sampling was performed after 5 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-coated to obtain 839.2 parts of the product (yield 93.2%). The obtained monoester compound was a pale yellow liquid having a viscosity at 25 ° C. of 630 mPa · s.

  As a result of analysis of this product, it was a compound having an acid value = 2.48, a saponification value = 69.89 (theoretical value = 69.8), and an IOB value = 0.16.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 3350.50 cm ⁻¹ (hydroxyl group) and 1738.90 cm ⁻¹ (ester).

<Comparative Example 3: Synthesis of dilauroyl sarcosine [2 mol] dimer diol [1 mol] ester>
864 parts of dimer diol and 736 parts of lauroyl sarcosine are charged, stirred, 8 parts of 50% sulfuric acid aqueous solution is added, and the temperature is raised to 130 ° C. while allowing nitrogen to flow. Sampling was performed after 5 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-coated to obtain 1488 parts (yield 93%) of the product. The obtained diester compound was a pale yellow liquid having a viscosity at 25 ° C. of 1740 mPa · s.

  As a result of analysis of this product, it was a compound having an acid value = 4.00, a saponification value = 103.5 (theoretical value = 107.0), and an IOB value = 0.40.

As a result of measuring the infrared absorption spectrum of the ester compound, characteristic absorption was observed at 1750 cm ⁻¹ , (ester) and 1658 cm ⁻¹ (amide).

<Comparative Example 4: Synthesis of pyroglutamic acid [1 mol] hexyldecanol [1 mol] ester>
First, 1316 parts of hexyldecanol and 684 parts of pyroglutamic acid are charged, stirred, 10 parts of paratoluenesulfonic acid is added, and the temperature is raised to 150 ° C. while allowing nitrogen to flow. Sampling was performed after 8 hours of reaction time, and the ester reaction was terminated at a predetermined acid value. The mixture was cooled with water, neutralized with a 20% aqueous sodium hydroxide solution at 70 to 80 ° C., dehydrated, and pre-filtered to obtain 1698 parts of the product (yield 84.9%). The obtained ester compound was a transparent liquid having a viscosity of 310 mPa · s at 25 ° C.

  As a result of analysis of this product, it was a compound having an acid value = 0.47, a saponification value = 163.53 (theoretical value = 159), and an IOB value = 0.66.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 3226.08 cm ⁻¹ (hydroxyl group), 1742.76 cm ⁻¹ (ester) and 1709.00 cm ⁻¹ (amide).

  Hereafter, the effect of the oil-based base which mix | blended one or more ester compounds obtained by the Example and the comparative example was evaluated with the compounding example.

A water retention test was performed using the diester compounds described in Examples 1 to 12 and the ester compounds shown in Comparative Examples 1 to 6. The result is shown in FIG. The measuring method is carried out by adding water while stirring 10 g of each oily base with a paddle at room temperature (20 ° C. to 25 ° C.), and repeating this until water does not enter. Then, it was left to stand at 25 ° C. for 12 hours, and the value obtained by removing the separated water was expressed as a percentage as the water holding power.
Comparative Example 1: Diisostearic acid dimer diol ester Comparative example 2: Monoisostearic acid dimer diol ester Comparative example 3: Dilauroyl sarcosine dimer diol ester Comparative example 4: Pyroglutamic acid hexyl decanol ester Comparative example 5: Lauroyl glutamic acid di (phytosterol / octyldodecanol) ) Esters [Ajinomoto Co.]
Comparative Example 6: Lanolin [manufactured by Croda Japan Co., Ltd.]

  As a result, in the ester compound having only one of the dimer diol group and pyroglutamic acid group of Comparative Examples 1 to 4, in most cases, the water retention performance is not exhibited, and in order to exhibit the water retention performance, It was proved that both dimer diol group and pyroglutamic acid group are essential in the structure. In addition, the compound consisting of a mixed ester of an acylamino acid, a sterol and a higher alcohol of Comparative Example 5 conventionally used as a water-holding oil showed approximately 400% water-holding power, but the esters of Examples 1 to 7 and 12 The compound showed a water holding power exceeding 1000% on average, and showed a water holding performance far exceeding that of the compound of Comparative Example 5.

  It is desirable that the oily base for cosmetics or external preparations can be in any form between liquid and solid depending on its use. Furthermore, in the case of liquids, the characteristics of the base are imparted to cosmetics or external preparations by responding widely from low viscosity to high viscosity, and in the case of solids from soft paste to solid. It becomes possible. Next, in a mixed ester compound of pyroglutamic acid, at least one selected from monovalent fatty acids and N-acylated amino acids, and dimer diol, at least one selected from monovalent fatty acids and N-acylated amino acids The base viscosity according to the charging ratio in the case where is isostearic acid was compared. The viscosity was measured at 25 ° C. with a BM viscometer (TVB-10, manufactured by Toki Sangyo Co., Ltd.). The results are shown in FIG.

  As a result, in Examples 2 to 4 in which the preparation ratio of pyroglutamic acid and isostearic acid was adjusted as compared with the compound of Example 1 which had a high viscosity close to a paste, it was 10000 mPa · s or less which can be easily blended into cosmetics or external preparations. A low-viscosity liquid compound was obtained. Thereby, it was shown that the base viscosity adapted to the application can be arbitrarily adjusted while maintaining the functionality.

  Furthermore, the oily base may be required for performance that contributes to the storage stability of cosmetics or external preparations. In particular, it is required to be stable in a temperature test. For example, if it is an oil agent that impairs fluidity at −5 ° C., it may affect the low-temperature stability of the formulated cosmetic or external preparation. Therefore, the properties (transparency and fluidity) at low temperatures required for compounds that become liquid at 25 ° C. were confirmed. The results are shown in Table 1. The test method visually judged the state after the ester compound of an Example and the ester compound shown to the comparative example were preserve | saved for 30 days in -5 degreeC environment.

  As a result, even in the compound of the example which becomes liquid at 25 ° C., it is stored in the environment of −5 ° C. as in Comparative Examples 4 and 5 depending on the blending ratio of the monovalent fatty acid and the type of N-acylated amino acid. Even in this case, it was confirmed that the oily base was excellent in fluidity and low-temperature characteristics that could maintain a transparent liquid state.

<Example 13 (emollient cream)>
An emollient cream having the composition shown in Table 3 below was prepared as follows. That is, component 1 is heated to 85 ° C. and component 2 is heated to 70 ° C., and dissolved so as to be substantially uniform. Next, component 1 was gradually added while stirring component 2.

  These emollient creams were subjected to sensory evaluation and emulsion stability evaluation by the following methods. The sensory evaluation of this product was conducted by five panelists, and the product properties when stored in an environment of 45 ° C. were judged by visual observation. If the cream was maintained, ○, fluid emulsion If it becomes, it will be written as x.

  The sensory evaluation criteria are shown in Table 2.

  Calculation of evaluation results: Very good (◎) when the evaluation value of each panel according to the above evaluation criteria is 1.0 to 2.0 (◎), good (○) when 0.5 to 1.0, -0. The case of 5 to 0.5 is determined to be slightly bad (Δ).

  As a result, the ester compound of Example 1 of the present invention is superior to the case of blending the ester compounds of Comparative Examples 4 to 6 in terms of good spreadability at coating and a feeling of film formation, and gives a sufficiently moist feeling after coating. Showed the sensuality.

<Example 14 (transparent hair shampoo)>
A transparent hair shampoo having the composition shown in Table 4 below was prepared as follows. That is, component 1 is heated to 70 ° C. and component 2 is heated to 75 ° C., and dissolved so as to be substantially uniform. Next, component 1 was gradually added while stirring component 2. Thereafter, component 3 was added and cooled to 30 ° C. This transparent hair shampoo imparted a moist and glossy feel to the hair and exhibited an excellent sensation for smooth finger application.

<Example 15 (pearl hair shampoo)>
A pearl hair shampoo having the composition shown in Table 5 below was prepared as follows. That is, component 1 is heated to 70 ° C. and component 2 is heated to 75 ° C., and dissolved so as to be substantially uniform. Next, component 1 was gradually added while stirring component 2, and then stirred at 40 ° C. for 1 hour to precipitate pearl crystals. This pearl hair shampoo was excellent in pearl appearance, and gave hair a moist and glossy feeling, and showed an excellent sensuality for smooth finger application.

<Example 16 (hair conditioner)>
A hair conditioner having the composition shown in Table 6 below was prepared as follows. That is, component 1 is heated to 75 ° C. and component 2 is heated to 80 ° C., and dissolved so as to be substantially uniform. Next, component 1 was gradually added while stirring component 2. Thereafter, component 3 was added and cooled to 30 ° C. This hair conditioner was not sticky, kept the moisture of the hair, imparted a glossy and moist feeling, and exhibited an excellent sensation for smooth fingering.

<Example 17 (hair styling wax)>
A hair styling wax having the composition shown in Table 7 below was prepared as follows. That is, component 1 is heated to 85 ° C. and component 2 is heated to 70 ° C., and dissolved so as to be substantially uniform. Next, component 1 was gradually added while stirring component 2. Then, it cooled to 40 degreeC and the component 3 was added. This hair styling wax was excellent in setting power, cared for hair damage and exhibited a moist feeling.

<Example 18 (emollient skin lotion)>
An emollient skin lotion having the composition shown in Table 8 below was prepared as follows. That is, component 1 and component 2 are each heated to 70 ° C. and dissolved so as to be substantially uniform. Next, component 1 was gradually added while stirring component 2. It was then cooled and component 3 was added at 40 ° C. This emollient skin lotion exhibited a sensuality that was excellent in spreading, familiarity and emollient.

<Example 19 (W / O emollient essence)>
W / O emollient essences having the compositions shown in Table 9 below were prepared as follows. That is, component 1 and component 2 are heated to 80 ° C. and dissolved so as to be substantially uniform. Next, component 2 was gradually added while stirring component 1. Thereafter, component 3 was added and cooled to 30 ° C. This W / O emollient essence had a sense of transparency, excellent film feeling, fresh skin, and a sensation that imparted a smooth feel.

<Example 20 (W / O foundation cream)>
W / O foundation creams having the compositions shown in Table 10 below were prepared as follows. That is, component 1 is heated to 70 ° C. and component 2 is heated to 75 ° C., and dissolved so as to be substantially uniform. Next, component 2 was gradually added while stirring component 1. This W / O foundation cream exhibited a sensation that gave a glossy finish with a smooth feel.

<Example 21 (sunscreen lotion)>
Sunscreen lotions having the compositions shown in Table 11 below were prepared as follows. That is, components 1 to 3 were dissolved so as to be substantially uniform at room temperature, and then components 2 and 3 were added while stirring component 1. This sunscreen lotion was excellent in quick-drying and showed a familiar sensation by suppressing breakage caused by sweat.

<Example 22 (lipstick)>
Lipsticks having the compositions shown in Table 12 below were prepared as follows. That is, component 1 is heated and dissolved, component 2 is added thereto, kneaded with a roll mill, and dispersed so as to be substantially uniform. Then, after defoaming and pouring into a mold, it was cooled rapidly to form a stick. This lipstick was excellent in familiarity and adhesion with the lips, and had good sensation that gave it a high gloss feeling.

<Example 23 (cleansing oil)>
Cleansing oils having the compositions shown in Table 13 below were prepared as follows. That is, the components 1 and 2 are dissolved at room temperature, and the components 2 are gradually added while stirring the components 1 so as to become transparent and substantially uniform. This cleansing oil has excellent low-temperature stability, is not only familiar with makeup stains such as foundations and mascara, but also has a moist feeling after washing, and a sensory performance that can be used even with wet hands. showed that.

<Example 24 (cleansing gel)>
Cleansing gels having the compositions shown in Table 14 below were prepared as follows. That is, after component 1 and component 2 were heated to 70 ° C. and dissolved so as to be substantially uniform, component 1 was gradually added while stirring component 2. This cleansing gel has excellent dispersibility, so it is well-familiar with makeup stains such as foundations and lipsticks, exhibits excellent cleansing performance, emulsifies quickly when washed, and gives a moist finish after washing showed that.

<Example 25 (cleansing cream)>
Cleansing creams having the compositions shown in Table 15 below were prepared as follows. That is, after component 1 and component 2 were heated to 70 ° C. and dissolved so as to be substantially uniform, component 2 was gradually added while stirring component 1. This cleansing cream was well-familiar with makeup stains such as foundations and lipsticks, showed excellent cleansing performance, and showed a moist finish after washing and a sensation that imparts elasticity to the skin.

<Example 26 (bath oil)>
A bath oil having the composition shown in Table 16 below was prepared as follows. That is, component 1 and component 2 were dissolved so as to be substantially uniform at room temperature, and then component 2 was added while stirring component 1. This bath oil is excellent in dispersibility in water and provides a bath environment with a strong opalescence. Moreover, the sensuality which gives the moist touch to the skin after bathing was shown.

  Application examples of the present invention include application of cosmetics and external preparations.

Claims (7)

It contains a mixed ester compound of dimer diol having at least one selected from pyroglutamic acid, monovalent fatty acid and N-acylated amino acid having the structure of the following general formula (I): Oily base.

(I)
Wherein R is at least one residue selected from the monovalent fatty acid and N-acylated amino acid used in the esterification reaction, and a, b, c and d are integers of 1 or more and a + b + c + d = (In addition, depending on the degree of esterification, a part of pyroglutamic acid group and RCO group is a hydroxyl group.) The oily base according to claim 1,
An oily base characterized by having a water holding power of 300% or more. The oily base according to claim 1 or 2,
The oily base, wherein the monovalent fatty acid is a linear fatty acid having 8 to 26 carbon atoms. The oily base according to claim 1 or 2,
The oil-based base, wherein the monovalent fatty acid is a branched fatty acid having 4 to 22 carbon atoms. The oily base according to claim 1 or 2,
An oily base, wherein the amino acid part of the N-acylated amino acid is selected from N-methylglycine or N-methyl-β-alanine.   Cosmetics containing the oil-based base of any one of Claims 1-5.   An external preparation comprising the oily base according to any one of claims 1 to 5.