JP2011178733A - N-long chain acyl acidic amino acid diester compound, and cosmetic and detergent obtained by using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an N-long chain acyl acidic amino acid diester compound having the same performance as a conventional N-long chain acyl acidic amino acid alkali salt or N-long chain acyl acidic amino acid diester, and also having a lower freezing point as compared with those of the conventional ones. <P>SOLUTION: This N-long chain acyl acidic amino acid diester compound is obtained by performing the esterification reaction of the N-long chain acyl acidic amino acid having 8 to 22C acyl with a mixture of branched chain higher alcohols having 18 mean number of carbon atoms. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to an N-long chain acyl acidic amino acid diester compound, and a cosmetic and a cleaning material using the same.

  N-long-chain acyl acidic amino acid alkali salts are used as water-soluble surfactants, and are known to have low toxicity, low skin irritation, and good biodegradability. However, this N-long chain acyl acidic amino acid alkali salt is difficult to dissolve in oils such as fats and oils and mineral oils.

  Therefore, in order to improve the solubility in oils while maintaining the preferable characteristics of the N-long chain acyl acidic amino acid alkali salt, the N-long chain acyl acidic amino acid salt is converted to a diester of an N-long chain acyl acidic amino acid. A converted version has been proposed (see, for example, Patent Documents 1 and 2).

Japanese Patent Publication No. 51-23395 Japanese Patent Publication No.56-12609

  However, conventional N-long-chain acyl acidic amino acid diesters cause partial solidification from a liquid state at a low temperature (for example, 5 ° C. or lower), crystals precipitate, or at a very low temperature (for example, 0 ° C. or lower). May solidify from liquid and change to solid, so the product performance does not change, but the appearance may change due to temperature change.

  In addition, for example, when producing cosmetics or cleaning materials using N-long chain acyl acidic amino acid diesters that have been coagulated at extremely low temperatures as raw materials, N-long chains are considered in consideration of uniform dispersion / mixing and production efficiency. It may be necessary to add a dissolution step in order to change the acyl acidic amino acid diester to a liquid state.

  An object of the present invention is to provide an N-long chain acyl acidic amino acid diester having the same performance as that of a conventional N-long chain acyl acidic amino acid alkali salt or N-long chain acyl acidic amino acid diester, and having a lower freezing point than conventional ones. It is to provide a compound.

  The acyl acidic amino acid diester compound of the present invention and cosmetics and cleaning agents using the same have the following characteristics.

  (1) N-long chain acyl obtained by esterifying N-long chain acyl acidic amino acid having an acyl group having 8 to 22 carbon atoms and a branched higher alcohol having an average of 18 carbon atoms It is an acidic amino acid diester compound.

  (2) N according to (1) above, wherein the mixture of branched higher alcohols having an average of 18 carbon atoms is a mixture of a branched higher alcohol having 16 carbon atoms and a branched higher alcohol having 20 carbon atoms. -A long-chain acyl acidic amino acid diester compound.

  (3) The mixture of branched higher alcohols having an average of 18 carbon atoms is one kind of branched higher alcohols having 18 carbon atoms, or two kinds of branched chain higher alcohols having 18 different carbon atoms at different positions. The N-long-chain acyl acidic amino acid diester compound according to (1), which is a mixture comprising the above.

  (4) The N-long chain acyl acidic amino acid diester according to the above (2), wherein the mixture of branched chain higher alcohols having an average of 18 carbon atoms further comprises one or more branched chain higher alcohols having 18 carbon atoms. A compound.

  (5) A cosmetic comprising the N-long-chain acyl acidic amino acid diester compound according to any one of (1) to (4) above.

  (6) A cleaning material comprising the N-long-chain acyl acidic amino acid diester compound according to any one of (1) to (4) above.

  According to the present invention, N-long-chain acyl acidic amino acid diesters having the same performance as conventional N-long-chain acyl acidic amino acid alkali salts and N-long-chain acyl acidic amino acid diesters and having a lower freezing point than conventional ones. A compound can be provided.

  Moreover, according to this invention, the cosmetics and washing | cleaning material which have a low freezing point compared with the past can be provided.

  Hereinafter, the present invention will be described in detail.

  The N-long chain acyl acidic amino acid diester compound in the present embodiment is a mixture of an N-long chain acyl acidic amino acid having an acyl group having 8 to 22 carbon atoms and a branched higher alcohol having an average of 18 carbon atoms. Is obtained by esterification reaction.

The acyl group of the N-long chain acyl acidic amino acid having 8 to 22 carbon atoms used in the present embodiment may be a mixture of different chain lengths within this range. Examples of the N-long chain acyl acidic amino acid include N-long chain acyl acidic glutamic acid and N-long chain acyl acidic aspartic acid. Among them, N-long chain acyl acidic glutamic acid is preferable. As these acidic amino acid components, any of D-form, L-form and DL-form can be used.

(However, in the formula, R is a fatty acid residue having 8 to 22 carbon atoms used in the acylation reaction.)

  Here, the “mixture of branched higher alcohols having an average of 18 carbon atoms” refers to a mixture of branched higher alcohols having different carbon numbers at a suitable mass ratio. For example, it may be a mixture of branched chain higher alcohols having 14, 16, 18, 20, and 22 carbon atoms. Examples of the branched chain higher alcohol having 14 carbon atoms include 2-tetradecyl alcohol (isomyristyl alcohol). Examples of the branched chain higher alcohol having 22 carbon atoms include 2-behenyl alcohol (isodocosa). Nol). The branched chain higher alcohols having 16, 18, and 20 carbon atoms will be described later.

  In addition, the mixture of branched higher alcohol having an average of 18 carbon atoms used in the present embodiment is a mixture of a branched higher alcohol having 16 carbon atoms and a branched higher alcohol having 20 carbon atoms. Examples of the branched chain higher alcohol having 16 carbon atoms include 2-hexyldecyl alcohol (isopalmityl alcohol), and examples of the branched chain higher alcohol having 20 carbon atoms include 2-octyldodecyl alcohol (isoeico). Sanol).

In the present embodiment, as a mixture of a branched higher alcohol having 16 carbon atoms and a branched higher alcohol having 20 carbon atoms, for example, 1: 1 mass of 2-hexyldecyl alcohol and 2-octyldodecyl alcohol shown below is used. A mixture of ratios is preferred.

  In addition, the mixture of other branched chain higher alcohols having an average of 18 carbon atoms used in this embodiment is one of the branched chain higher alcohols having 18 carbon atoms, or the number of carbon atoms having 18 different chain positions. It is a mixture comprising two or more kinds of branched chain higher alcohols. Examples of the branched chain higher alcohol having 18 carbon atoms include 2-hexyldecyl alcohol and 2-octyldecyl alcohol called isostearyl alcohol.

As a mixture of two types of the C18 branched higher alcohol having different positions of the latter branched chain, for example, a 1: 1 mass ratio mixture of 2-hexyldecyl alcohol and 2-octyldecyl alcohol is preferable.

  As a mixture of other branched chain higher alcohols having an average of 18 carbon atoms used in the present embodiment, the above mixture of a branched chain higher alcohol having 16 carbon atoms and a branched chain higher alcohol having 20 carbon atoms is further added. One or more of the above-described branched chain higher alcohols having 18 carbon atoms may be mixed.

  By using a mixture of branched higher alcohols having an average of 18 carbon atoms in the ester portion of the N-long-chain acyl acidic amino acid diester compound, compared to the case of using one kind of branched higher alcohol having 18 carbon atoms. , The freezing point temperature of the N-long chain acyl acidic amino acid diester compound can be lowered, and low-temperature flow stability can be obtained.

As the N-long chain acyl acidic amino acid diester compound in the present embodiment, for example, the following structure is preferable. In the formula, R is a branched higher alcohol residue derived from the above-mentioned mixture of branched higher alcohols having an average carbon number of 18.

(In the formula, R is a fatty acid residue having 8 to 22 carbon atoms used in the acylation reaction, and R ′ and R ″ are branched higher alcohol residues used in the esterification reaction.)

  The N-long chain acyl acidic amino acid diester compound in the present embodiment includes the above-described N-long chain acyl acidic amino acid having an acyl group having 8 to 22 carbon atoms and a branched higher alcohol having an average of 18 carbon atoms. It can be obtained by esterification reaction with a mixture. As the esterification reaction method, for example, heating (normal pressure or reduced pressure) dehydration condensation reaction, transesterification reaction, azeotropic dehydration condensation reaction is used. An azeotropic dehydration condensation reaction is preferable from the viewpoint of the yield and purity of the product.

  The blending amount of the N-long chain acyl acidic amino acid diester compound in the present embodiment to the cosmetic and cleaning material is not particularly limited, but is preferably about 0.1% by mass to 50% by mass, more preferably 0. 0.5 mass% to 30 mass%.

  One or more N-long chain acyl acidic amino acid diester compounds used in the present embodiment are cleansing oil, facial cleansing foam, cleansing cream, cleansing gel, massage cream, cold cream, emollient cream, moisture cream, hand cream, Emollient emulsion, moisture emulsion, hand emulsion, lotion, pack, foundation, lipstick, press powder, eye shadow, tic, hair liquid, set lotion, permanent wave solution, hair cream, hair lotion, hair mousse, hair wax, hair gel, shampoo , Hair rinse, hair conditioner, body shampoo, solid detergent, liquid detergent, antiperspirant, after shaving cream, sunscreen cream, sunscreen oy , Hair growth agents, hair tonics, bath agents, can be used as a nonionic surfactant upon adjustment of the cosmetic and cleansing compositions, such as pharmaceutical composition for external application. There are no particular restrictions on the dosage form of cosmetics and cleaning agents, and any emulsification system, solubilization system, solution system, powder dispersion system, water-oil two-layer system, water-oil-powder three-layer system, etc. It may be a dosage form.

  The cosmetics and cleaning agents of the present embodiment include, as oil phase materials, saturated or unsaturated fatty acids and higher alcohols obtained therefrom, squalane, castor oil and derivatives thereof, lanolins including beeswax, liquid and refined lanolin, and Derivatives thereof, cholesterol and derivatives thereof, macadamia nut oil, jojoba oil, carnauba wax, sesame oil, cacao oil, palm oil, mink oil, molefish, candelilla wax, whale wax and other oil phase raw materials, paraffin, microcrystalline wax, Oil phase raw materials derived from petroleum and minerals such as liquid paraffin, petrolatum, ceresin, methylpolysiloxane, polyoxyethylene / methylpolysiloxane, polyoxypropylene / methylpolysiloxane, poly (oxyethylene / oxypropylene) / methylpolysiloxane S , Silicones such as silicone polymers such as methylphenyl polysiloxane, fatty acid-modified polysiloxane, aliphatic alcohol-modified polysiloxane, amino acid-modified polysiloxane, resin acids, esters, ketones, oily components, The dimer acid ester, dimer diol ester, polyoxyalkylene dimer acid ester, and polyoxyalkylene dimer diol ester of the present invention can be used in combination as long as the effects of the nonionic surfactant are not impaired.

  In addition, the cosmetic and cleaning materials of the present embodiment include other interfaces within a range that does not inhibit the effects of the N-long-chain acyl acidic amino acid diester compound or nonionic surfactant composition used in the present embodiment. N-long chain acyl amino acid salts such as N-long chain acyl acidic amino acid salts and N-acyl neutral amino acid salts; N-long chain fatty acid acyl-N-methyltaurine salts, alkyl sulfates and alkylene oxide adducts as activators , Fatty acid amide ether sulfates, fatty acid metal salts and weak bases, sulfosuccinic acid surfactants, alkyl phosphates and their alkylene oxide adducts, alkyl ether carboxylic acid and other anionic surfactants; higher alcohols and their alkylene oxide adducts Ether type nonionic surfactant such as glycerin ester and its Ether ester type nonionic surfactants such as a ruxylene oxide adduct, sorbitan ester and its alkylene oxide adduct; fatty acid ester, glycerin ester, fatty acid polyglycerin ester, N-long chain acyl peptide polyglycerin ester, sorbitan ester, Ester-type nonionic surfactants such as sugar fatty acid esters; Nonionic surfactants such as alkyl glucosides, hydrogenated castor oil pyroglutamic acid diester and its alkylene oxide adducts, and fatty acid alkanolamides, etc .; alkylammonium chlorides , Aliphatic amine salts such as dialkylammonium chloride, quaternary ammonium salts thereof, aromatic quaternary ammonium salts such as benzalkonium salt, fatty acyl arginine esters, etc. Various surfactants such as thione surfactants; and betaine surfactants such as carboxybetaine; aminocarboxylic acid type surfactants; imidazoline type surfactants; , Dimer diol ester and polyoxyalkylene dimer acid ester, polyoxyalkylene dimer diol ester or nonionic surfactant composition thereof can be added.

  Furthermore, the cosmetics and cleaning agents of the present embodiment include, as an aqueous phase component, amino acids such as glycine, alanine, serine, threonine, arginine, glutamic acid, aspartic acid, leucine, and valine; glycerin, ethylene glycol, 1, Polyhydric alcohols such as 3-butylene glycol, propylene glycol and dipropylene glycol; polyamino acids including polyglutamic acid and polyaspartic acid and salts thereof, polyethylene glycol, gum arabic, alginate, xanthan gum, hyaluronic acid, hyaluronic acid salt, Chitin, chitosan, water-soluble chitin, carboxyvinyl polymer, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropyltrimethylammonium chloride, polydimethylmethylenepiperidi , Quaternary ammonium of polyvinylpyrrolidone derivatives, cationized protein, collagen degradation product and derivatives thereof, water-soluble polymers such as acylated protein, polyglycerol, amino acid polyglycerol ester; sugar alcohols such as mannitol and alkylene oxide adducts thereof; In addition, lower alcohols such as ethanol and propanol can be blended.

  Furthermore, examples of additives and medicines that are blended in the cosmetics and cleaning agents of the present embodiment include those that are usually blended in cosmetics and cleaning agents. For example, preservatives such as paraben derivatives, fragrances, pigments, pearlizing agents, antioxidants, bactericides, anti-inflammatory agents, analgesics, antifungal agents, keratin softening release agents, UV absorbers, UV scattering agents, hair restorers , Whitening agents, antiperspirants, sweat deodorants, vitamins, pH adjusters, hormone agents, viscosity adjusters, herbal medicines and the like can be blended.

  Use amount of the above-mentioned N-long chain acyl acidic amino acid diester compound or a nonionic surfactant containing one or more of these as an active ingredient to be blended in cosmetics and detergents prepared by appropriately blending the above components Is usually in the range of 0.01 to 100% by mass (the nonionic surfactant of the present invention can be used as it is, for example, as a makeup remover without adding other components) Preferably, it is 0.1-50 mass%.

  One embodiment of the present invention will be described below, but the present invention is not limited thereto. In the examples, unless otherwise specified, “part” represents “part by mass” and “%” represents “% by mass”.

Example 1: Synthesis of a mixture of N-lauroylglutamic acid 2-hexyldecyl alcohol diester compound and N-lauroylglutamic acid 2-octyldodecyl alcohol diester compound;
278 g of hexyl decyl alcohol “Risonol 16SP” (manufactured by Higher Alcohol Industry Co., Ltd.) and 343 g of octyldodecyl alcohol “Risonol 20SP” (manufactured by Higher Alcohol Industry Co., Ltd.) were heated to 50-60 ° C. under nitrogen filling, and N-lauroyl -379g of L-glutamic acid "Amisoft LA-D" (Ajinomoto Co., Inc.) is added. 5 g of p-toluenesulfonic acid is added as a catalyst, the temperature is raised to 130 ° C. over 1 to 2 hours, and the reaction is carried out for 4 to 5 hours until the acid value reaches 3.5, followed by cooling. After that, under nitrogen sealing at 50 to 60 ° C., 135% of the acid value neutralization amount of 3% -sodium hydroxide aqueous solution is added and stirred for 1 hour for deoxidation. Further, 150 g of ion-exchanged water was added under nitrogen sealing, and the mixture was stirred for 1 hour while being heated to 60 to 70 ° C., washed with water, dehydrated under reduced pressure, and filtered to obtain 830 g of the desired lauroylglutamic acid diester compound ( Yield 83%) was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 0.09, a hydroxyl value of 7.92, and a saponification value of 133.76.

As a result of measuring the infrared absorption spectrum of the above compound, a mixture of N-lauroylglutamic acid 2-hexyldecyl alcohol diester compound and N-lauroylglutamic acid 2-octyldodecyl alcohol diester had wavelengths of 1739.87 cm ⁻¹ (ester) and 1653. Characteristic absorption was observed at 0.07 cm ⁻¹ (amide).

Example 2: Synthesis of a mixture of N-lauroylglutamic acid 2-hexyldecyl alcohol diester compound and N-lauroylglutamic acid 2-octyldecyl alcohol diester compound;
620 g of isostearyl alcohol “Risonol 18SP” (manufactured by Higher Alcohol Industry Co., Ltd.) was heated to 50-60 ° C. under nitrogen filling, and 380 g of N-lauroyl-L-glutamic acid “Amisoft LA-D” (manufactured by Ajinomoto Co., Inc.) Added. 5 g of p-toluenesulfonic acid is added as a catalyst, the temperature is raised to 130 ° C. over 1 to 2 hours, and the reaction is carried out for 4 to 5 hours until the acid value reaches 3.5, followed by cooling. After that, under nitrogen sealing at 50 to 60 ° C., 135% of the acid value neutralization amount of 3% -sodium hydroxide aqueous solution is added and stirred for 1 hour for deoxidation. Further, 150 g of ion-exchanged water was added under nitrogen sealing, and the mixture was stirred for 1 hour while being heated to 60 to 70 ° C., washed with water, dehydrated under reduced pressure, and filtered to obtain 830 g of the desired lauroylglutamic acid diester compound ( Yield 83%) was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 0.07, a hydroxyl value of 9.49, and a saponification value of 132.12.

As a result of measuring the infrared absorption spectrum of the above compound, a mixture of N-lauroylglutamic acid 2-hexyldecyl alcohol diester compound and N-lauroylglutamic acid 2-octyldecyl alcohol diester had wavelengths of 1739.87 cm ⁻¹ (ester) and 1654. Characteristic absorption was observed in 0.03 cm ⁻¹ (amide).

Example 3: Synthesis of a mixture of N-lauroylglutamic acid 2-hexyldecyl alcohol diester compound, N-lauroylglutamic acid isostearyl alcohol diester compound, and N-lauroylglutamic acid 2-octyldodecyl alcohol diester compound;
139 g of hexyldecyl alcohol “Lisonol 16SP” (manufactured by Higher Alcohol Industry Co., Ltd.), 311 g of isostearyl alcohol “Lisonol 18SP” (manufactured by Higher Alcohol Industry Co., Ltd.) and 171 g of octyldodecyl alcohol “Lisonol 20SP” (manufactured by Higher Alcohol Industry Co., Ltd.) The temperature is raised to 50-60 ° C. under nitrogen sealing, and 379 g of N-lauroyl-L-glutamic acid “Amisoft LA-D” (manufactured by Ajinomoto Co., Inc.) is added. 5 g of p-toluenesulfonic acid is added as a catalyst, the temperature is raised to 130 ° C. over 1 to 2 hours, and the reaction is carried out for 4 to 5 hours until the acid value reaches 3.5, followed by cooling. After that, under nitrogen sealing at 50 to 60 ° C., 135% of the acid value neutralization amount of 3% -sodium hydroxide aqueous solution is added and stirred for 1 hour for deoxidation. Further, 150 g of ion-exchanged water was added under nitrogen sealing, and the mixture was stirred for 1 hour while being heated to 60 to 70 ° C., washed with water, dehydrated under reduced pressure, and filtered to obtain 830 g of the desired lauroylglutamic acid diester compound ( Yield 83%) was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 0.03, a hydroxyl value of 7.85, and a saponification value of 129.26.

As a result of measuring the infrared absorption spectrum of the above compound, a mixture of N-lauroylglutamic acid 2-hexyldecyl alcohol diester compound, N-lauroylglutamic acid isostearyl alcohol, and N-lauroylglutamic acid 2-octyldodecyl alcohol diester has a wavelength of 1739. Characteristic absorption was observed at .87 cm ⁻¹ (ester) and 1654.03 cm ⁻¹ (amide).

Example 4: Synthesis of a mixture of N-coconut oil fatty acid acylglutamic acid 2-hexyldecyl alcohol diester compound and N-coconut oil fatty acid acylglutamic acid 2-octyldodecyl alcohol diester compound;
277 g of hexyl decyl alcohol “Risonol 16SP” (manufactured by Higher Alcohol Industry Co., Ltd.) and 340 g of octyldodecyl alcohol “Lisonol 20SP” (manufactured by Higher Alcohol Industry Co., Ltd.) are heated to 50-60 ° C. under nitrogen filling, and N-coconut 383 g of oil fatty acid acyl-L-glutamic acid “Amisoft CA” (manufactured by Ajinomoto Co., Inc.) is added. 5 g of p-toluenesulfonic acid is added as a catalyst, the temperature is raised to 130 ° C. over 1 to 2 hours, and the reaction is carried out for 4 to 5 hours until the acid value reaches 3.5, followed by cooling. After that, under nitrogen sealing at 50 to 60 ° C., 135% of the acid value neutralization amount of 3% -sodium hydroxide aqueous solution is added and stirred for 1 hour for deoxidation. Furthermore, 150 g of ion-exchanged water was added under nitrogen sealing, and after stirring for 1 hour while raising the temperature to 60 to 70 ° C., washing with water was performed, followed by dehydration under reduced pressure and filtration to obtain the desired palm oil fatty acid acyl glutamic acid diester. 830 g of compound (yield 83%) was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 0.02, a hydroxyl value of 9.61, and a saponification value of 133.1.

As a result of measuring the infrared absorption spectrum of the above compound, a mixture of N-coconut oil fatty acid acylglutamic acid 2-hexyldecyl alcohol diester compound and N-coconut oil fatty acid acylglutamic acid 2-octyldodecyl alcohol diester has a wavelength of 1739.87 cm ^−. Characteristic absorption was observed for ¹ (ester) and 1954.03 cm ⁻¹ (amide).

Example 5: Synthesis of a mixture of N-stearoyl glutamic acid 2-hexyldecyl alcohol diester compound and N-stearoyl glutamic acid 2-octyldodecyl alcohol diester compound;
N-stearoyl was heated to 50-60 ° C. under nitrogen filling 250 g of hexyl decyl alcohol “Lisonol 16SP” (manufactured by Higher Alcohol Industry Co., Ltd.) and 307 g of octyldodecyl alcohol “Lisonol 20SP” (manufactured by Higher Alcohol Industry Co., Ltd.). -443g of L-glutamic acid "Amisoft HA-P" (made by Ajinomoto Co., Inc.) is added. 5 g of p-toluenesulfonic acid is added as a catalyst, the temperature is raised to 130 ° C. over 1 to 2 hours, and the reaction is carried out for 4 to 5 hours until the acid value reaches 3.5, followed by cooling. After that, under nitrogen sealing at 50 to 60 ° C., 135% of the acid value neutralization amount of 3% -sodium hydroxide aqueous solution is added and stirred for 1 hour for deoxidation. Further, 150 g of ion-exchanged water was added under nitrogen sealing, and the mixture was stirred for 1 hour while being heated to 60 to 70 ° C., washed with water, dehydrated under reduced pressure, filtered, and 830 g of the desired stearoyl glutamic acid diester compound. (Yield 83%) was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 0.04, a hydroxyl value of 123.1, and a saponification value of 9.17.

As a result of measuring the infrared absorption spectrum of the above compound, a mixture of N-stearoyl glutamic acid 2-hexyldecyl alcohol diester compound and N-stearoyl glutamic acid 2-octyldodecyl alcohol diester had wavelengths of 1739.87 cm ⁻¹ (ester) and 1654. Characteristic absorption was observed in 0.03 cm ⁻¹ (amide).

Comparative Example 1: Synthesis of N-lauroylglutamic acid 2-hexyldecyl alcohol diester compound;
595 g of hexyl decyl alcohol “Risonol 16SP” (manufactured by Higher Alcohol Industry Co., Ltd.) is heated to 50-60 ° C. under nitrogen filling, and 405 g of N-lauroyl-L-glutamic acid “Amisoft LA-D” (manufactured by Ajinomoto Co., Inc.) Added. 5 g of p-toluenesulfonic acid is added as a catalyst, the temperature is raised to 130 ° C. over 1 to 2 hours, and the reaction is carried out for 4 to 5 hours until the acid value reaches 5.6, followed by cooling. After that, under nitrogen sealing at 50 to 60 ° C., 135% of the acid value neutralization amount of 3% -sodium hydroxide aqueous solution is added and stirred for 1 hour for deoxidation. Further, 150 g of ion-exchanged water was added under nitrogen sealing, and the mixture was stirred for 1 hour while being heated to 60 to 70 ° C., washed with water, dehydrated under reduced pressure, and filtered to obtain 830 g of the desired lauroylglutamic acid diester compound ( Yield 83%) was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 0.18, a hydroxyl value of 9.31 and a saponification value of 142.61.

As a result of measuring the infrared absorption spectrum of the above compound, N-lauroylglutamic acid 2-hexyldecyl alcohol diester compound showed characteristic absorption at wavelengths of 1738.90 cm ^-1 (ester) and 1652.10 cm ^-1 (amide). It was.

Comparative Example 2: Synthesis of N-lauroylglutamic acid 2-octyldodecyl alcohol diester compound;
644 g of octyldodecyl alcohol “Risonol 20SP” (manufactured by Higher Alcohol Industry Co., Ltd.) was heated to 50-60 ° C. under nitrogen filling, and 356 g of N-lauroyl-L-glutamic acid “Amisoft LA-D” (manufactured by Ajinomoto Co., Inc.) Added. 5 g of p-toluenesulfonic acid is added as a catalyst, the temperature is raised to 130 ° C. over 1 to 2 hours, and the reaction is carried out for 4 to 5 hours until the acid value reaches 5.1, followed by cooling. After that, under nitrogen sealing at 50 to 60 ° C., 135% of the acid value neutralization amount of 3% -sodium hydroxide aqueous solution is added and stirred for 1 hour for deoxidation. Further, 150 g of ion-exchanged water was added under nitrogen sealing, and the mixture was stirred for 1 hour while being heated to 60 to 70 ° C. and washed with water, followed by dehydration under reduced pressure and filtration to obtain 870 g of the desired lauroyl glutamic acid diester compound ( Yield 87%).

  As a result of analysis of this product, it was a compound having an acid value of 0.17, a hydroxyl value of 8.23, and a saponification value of 122.11.

As a result of measuring the infrared absorption spectrum of the above compound, N-lauroylglutamic acid 2-octyldodecyl alcohol diester compound showed characteristic absorption at wavelengths of 1738.90 cm ⁻¹ (ester) and 1654.03 cm ⁻¹ (amide). It was.

Comparative Example 3: Synthesis of N-lauroylglutamic acid isostearyl alcohol diester compound and N-lauroylglutamic acid 2-octyldodecyl alcohol diester compound;
The temperature of isostearyl alcohol “Lisonol 18SP” (manufactured by Higher Alcohol Industry Co., Ltd.) 301 g and octyldodecyl alcohol “Lisonol 20SP” (manufactured by Higher Alcohol Industry Co., Ltd.) 332 g was raised to 50-60 ° C. under nitrogen filling, and N-lauroyl -367g of L-glutamic acid "Amisoft LA-D" (made by Ajinomoto Co., Inc.) is added. 5 g of p-toluenesulfonic acid is added as a catalyst, the temperature is raised to 130 ° C. over 1 to 2 hours, and the reaction is carried out for 4 to 5 hours until the acid value reaches 3.5, followed by cooling. After that, under nitrogen sealing at 50 to 60 ° C., 135% of the acid value neutralization amount of 3% -sodium hydroxide aqueous solution is added and stirred for 1 hour for deoxidation. Further, 150 g of ion-exchanged water was added under nitrogen sealing, and the mixture was stirred for 1 hour while being heated to 60 to 70 ° C., washed with water, dehydrated under reduced pressure, and filtered to obtain 830 g of the desired lauroylglutamic acid diester compound ( Yield 83%) was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 0.07, a hydroxyl value of 10.74, and a saponification value of 126.96.

As a result of measuring the infrared absorption spectrum of the above compound, the N-lauroylglutamic acid 2-hexyldecyl alcohol diester compound showed characteristic absorption at wavelengths of 1739.87 cm ⁻¹ (ester) and 1653.07 cm ⁻¹ (amide). It was.

[Low temperature characteristics test]
Samples of the N-long-chain acyl acidic amino acid diester compounds of Examples 1 to 5 and Comparative Examples 1 to 3 were put into 100 g bottle containers with an inner stopper, and these were placed at 5 ° C., −5 ° C., −10, respectively. It put into the constant temperature room of -20 degreeC and observed the property visually for every fixed time. The evaluation shown in Table 1 is as follows.
CL: Transparent liquid CLH: Transparent high viscosity liquid WS: White solid LS: Crystal precipitation

  Hereinafter, the results of evaluating the effect of the N-long chain acyl acidic amino acid diester compound of the present invention or the nonionic surfactant composition using one or more of them as an active ingredient will be specifically shown by blending examples.

Example 6: Emulsion type UV cake;
An emulsion type UV base cake having the composition shown in Table 2 below was prepared as follows. That is, component 1 was heated to 85 ° C. and component 2 was heated to 80 ° C., and component 2 was gradually added while stirring component 1. Component 3 was then added and filled before solidifying. This emulsion type UV cake exhibits excellent sensory properties with good stability, glossiness and elongation, and can be widely applied to makeup bases, functionality, cake type foundations and the like.

Example 7: Emulsion cake foundation;
An emulsion cake foundation having the composition shown in Table 3 below was prepared as follows. That is, component 1 was heated to 85 ° C. and component 2 was heated to 80 ° C., and component 2 was gradually added while stirring component 1. Component 3 was then added and filled before solidifying. This emulsion cake foundation had a smooth feel and a high quality appearance with a natural luster.

Example 8: Moisture cream;
A moisture cream having the composition shown in Table 4 below was prepared as follows. That is, after component 1 was heated to 75 ° C. and component 2 was heated to 80 ° C. and dissolved uniformly, component 2 was added while stirring component 1. This moisture cream was excellent in stability and showed a sensation that moisturizes and gives elasticity to the skin.

Example 9: Foundation cream;
A foundation cream having the composition shown in Table 5 below was prepared as follows. That is, component 1 was heated to 70 ° C. and component 2 was heated to 75 ° C. and dissolved uniformly, and then component 2 was added while stirring component 1. This foundation cream showed a sensation that gave a glossy finish with a smooth feel.

Example 10: Emollient milky lotion;
The emollient milky lotion having the composition shown in Table 6 below was prepared as follows. That is, component 1 is dispersed with good stirring at room temperature. Next, after the component 2 was uniformly dissolved at room temperature, the component 2 was gradually added while stirring the component 1. This emollient milky lotion showed a sensation that imparted freshness and moisture to the skin.

Example 11: Emollient cream;
An emollient cream having the composition shown in Table 7 below was prepared as follows. That is, component 1 and component 2 were heated to 60 ° C. and dissolved uniformly, and then component 2 was gradually added while stirring component 1. This emollient cream was excellent in stability and showed a sensation that moisturized the skin.

Example 12: Emollient essence;
The emollient essence having the composition shown in Table 8 below was prepared as follows. That is, component 1 and component 2 were heated to 80 ° C. and dissolved uniformly, and then component 2 was gradually added while stirring component 1. Next, component 3 was added and stirred. This emollient essence had a sense of transparency, fresh skin, and a sensation that imparted a smooth feel.

Example 13: Sunscreen lotion;
A sunscreen lotion having the composition shown in Table 9 below was prepared as follows. That is, component 1 was mixed at room temperature, components 2 and 3 were uniformly dissolved at room temperature, and then components 2 and 3 were added while stirring component 1. This sunscreen lotion suppressed the breakage caused by sweat and showed a familiar sensuality.

Example 14: Hair styling wax;
A hair styling wax having the composition shown in Table 10 below was prepared as follows. That is, component 1 was heated to 80 ° C. and component 2 was heated to 70 ° C. and dissolved uniformly, and then 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, and also showed a moist sensation by taking care of hair damage.

Example 15: Pearl hair shampoo;
A pearl hair shampoo having the composition shown in Table 11 below was prepared as follows. That is, component 1 was heated to 70 ° C. and component 2 was heated to 75 ° C. and dissolved uniformly, and then component 1 was added while stirring component 2. This pearl hair shampoo imparted moist feeling and gloss to the hair, and showed excellent sensuality as a smooth finger.

Example 16: Hair conditioner;
A hair conditioner having the composition shown in Table 12 below was prepared as follows. That is, component 1 was heated to 75 ° C. and component 2 was heated to 80 ° C. and dissolved uniformly, and then component 1 was added while stirring component 2. This hair conditioner kept the moisture of the hair, gave gloss and moist feeling, and showed excellent sensuality as a smooth finger.

Example 17: Body shampoo;
A body shampoo having the composition shown in Table 13 below was prepared as follows. That is, component 1 and component 2 were heated to 70 ° C. and dissolved uniformly, and then component 1 was added while stirring component 2. This body shampoo was excellent in foaming and showed a moist sensation.

Example 18 Cleansing Gel;
A cleansing gel having the composition shown in Table 14 below was prepared as follows. That is, after component 1 and component 2 were heated to 70 ° C. and dissolved uniformly, component 1 was gradually added while stirring component 2. This cleansing gel was well-suited for foundations, makeup and the like, and showed excellent cleansing performance.

Example 19: Cleansing oil;
A cleansing oil having the composition shown in Table 15 below was prepared as follows. That is, after component 1 and component 2 were heated to 70 ° C. and dissolved uniformly, component 1 was gradually added while stirring component 2. This cleansing oil is a 2-way type that can be used even with wet hands, and is well-familiar with foundations, makeup, etc., and showed excellent cleansing performance.

Example 20: cleansing cream;
A cleansing cream having the composition shown in Table 16 below was prepared as follows. That is, after component 1 was heated to 80 ° C. and component 2 was heated to 70 ° C. and dissolved uniformly, component 2 was gradually added while stirring component 1. This cleansing cream was well-suited for foundation, makeup, etc., had excellent cleansing performance, and exhibited a sensation that gave a moist feel after washing.

Example 21: Bath oil Bath oil having the composition shown in Table 17 below was prepared as follows. That is, after component 1 and component 2 were uniformly dissolved at room temperature, 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 cleaning materials.

Claims (6)

  N-long characterized by being obtained by esterifying N-long-chain acyl acidic amino acid having an acyl group having 8 to 22 carbon atoms and a branched higher alcohol having an average of 18 carbon atoms. Chain acyl acidic amino acid diester compounds.   The mixture of branched higher alcohol having an average of 18 carbon atoms is a mixture of a branched higher alcohol having 16 carbon atoms and a branched higher alcohol having 20 carbon atoms. N-long chain acyl acidic amino acid diester compounds.   The mixture of branched chain higher alcohols having an average of 18 carbon atoms is composed of one or more branched chain higher alcohols having 18 carbon atoms, or two or more kinds of branched chain higher alcohols having 18 carbon atoms having different branch chain positions. The N-long-chain acyl acidic amino acid diester compound according to claim 1, which is a mixture.   The N-long-chain acyl acidic amino acid according to claim 2, wherein the mixture of branched higher alcohols having an average of 18 carbon atoms further contains one or more branched chain higher alcohols having 18 carbon atoms. Diester compound.   A cosmetic comprising the N-long-chain acyl acidic amino acid diester compound according to any one of claims 1 to 4.   A cleaning material comprising the N-long-chain acyl acidic amino acid diester compound according to any one of claims 1 to 4.