JP4912175B2 - Oil base - Google Patents

Description

  The present invention relates to an oily base containing an ester of an acylamino acid and a dimer diol and / or an ester of an acylamino acid, a fatty acid and a dimer diol, and an emulsion stability and a pigment dispersibility for a formulation containing the oily base. The present invention relates to cosmetics and external preparations excellent in feeling of use.

Conventionally, oily raw materials containing various ester compounds, that is, oily bases, have been used in cosmetics and external preparations. For example, hexyl laurate, isostearyl laurate, isopropyl myristate, isocetyl myristate, octyldodecyl myristate, cetyl palmitate, isopropyl palmitate, 2-ethylhexyl palmitate, stearyl stearate, diethylene glycol dioleate, diisostearate Triethylene glycol acid, propylene glycol dioleate, propylene glycol distearate, glyceryl tricaprate, glyceryl trioleate, glyceryl tristearate, and the like are used.
Further, as an ester compound using dimer diol, a compound with a monocarboxylic acid having 4 to 34 carbon atoms or a dicarboxylic acid has been reported as an oil agent excellent in stability, safety, feeling of use and the like (Patent Document 1). ).
JP 2001-72530 A

However, these ester compounds are not always satisfactory as oily bases for cosmetics and external preparations in terms of emulsion stability, pigment dispersibility, and feeling of use with respect to the blended components. Therefore, an oily base excellent in the stability, pigment dispersibility, and feeling of use has been desired.
An object of the present invention is to provide such an oily base and cosmetics and external preparations containing the same.

  As a result of intensive studies to solve the above problems, the present inventors have found that an oily base containing an ester of acylamino acid and dimer diol and / or an ester of acylamino acid, fatty acid and dimer diol is a cosmetic. As a raw material for external preparations, they have found that they are excellent in emulsion stability, feeling of use, pigment dispersibility and the like, thereby completing the present invention.

The present invention is as follows.
(1) An oily base containing an ester of an acyl amino acid and a dimer diol and / or an ester of an acyl amino acid, a fatty acid and a dimer diol.
(2) The oily base according to the above (1), wherein the fatty acid has 2 to 26 carbon atoms.
(3) The oily base according to (1) or (2) above, wherein the amino acid of the acylamino acid is an amino acid selected from neutral amino acids and acidic amino acids.
(4) The above (1), wherein the amino acid of the acylamino acid is an amino acid selected from glycine, alanine, threonine, β-alanine, sarcosine, N-methyl-β-alanine, aminobutyric acid, glutamic acid, and aspartic acid. Or the oil-based base as described in (2).
(5) A cosmetic or external preparation comprising the oily base according to any one of (1) to (4) above.

  The oily base according to the present invention is excellent in dispersibility of compounding components (eg, pigments), has good emulsification stability, and is preferable in terms of safety, and cosmetics and external preparations containing the same. Can also be made excellent in terms of performance and functionality.

  In the present invention, the oily base is widely used in creams, emulsions, and the like having functions such as an emollient effect such as a skin softening action, a protective action, a moisture evaporation inhibiting action, an improvement in use feeling, and a cleansing action. It is a fat-soluble component. In addition, it is blended in products such as foundations and lipsticks for the purpose of improving pigment dispersion and appearance, and imparting cosmetic properties to pigments to enhance cosmetic effects. Furthermore, in hair care cosmetics, it has a role of giving glossiness and setability to hair, and is used as an oily base for cosmetics and external preparations according to each purpose of use.

In the present invention, the dimer diol is one in which the carboxyl group portion of the 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 to convert the carboxyl group portion of dimer acid to 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. For example, myristoleic acid, palmitoleic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, erucic acid, linoleic acid, linolenic acid, arachidonic acid and the like are preferred as examples of unsaturated fatty acids to be dimerized. The dimer 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 a substance mainly composed of a diol having usually 22 to 44 carbon atoms, preferably 24 to 40 carbon atoms, and more preferably about 36 carbon atoms. 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 the present invention can be used. 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.

  The acyl group in the acylamino acid moiety of the ester of the present invention is preferably an alkanoyl group, and the carbon number thereof is usually 2 to 26, preferably 2 to 22, and more preferably 12 to 18. For example, straight chain saturated fatty acids such as acetic acid, butanoic acid, hexanoic acid, octanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, linolenic acid, elaidic acid, etc. Examples thereof include those derived from chain unsaturated fatty acids, branched fatty acids such as isobutanoic acid, isopentanoic acid, isohexanoic acid, 2-ethylhexanoic acid, 2-hexyldecanoic acid and isostearic acid.

  The type of amino acid in the acylamino acid part of the ester of the present invention is not particularly limited, but is preferably a neutral amino acid or an acidic amino acid. Examples of suitable amino acids include glycine, alanine, threonine, β-alanine, sarcosine, N-methyl-β-alanine, aminobutyric acid, glutamic acid, and aspartic acid.

  Moreover, as a fatty acid which comprises the fatty acid origin part of the ester regarding this invention, a C2-C26 fatty acid is preferable, for example, an acetic acid, butanoic acid, hexanoic acid, octanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid , Linear saturated fatty acids such as behenic acid, linear unsaturated fatty acids such as oleic acid, linoleic acid, linolenic acid, elaidic acid, isobutanoic acid, isopentanoic acid, isohexanoic acid, 2-ethylhexanoic acid, 2-hexyldecane Examples thereof include branched fatty acids such as acids and isostearic acid.

  The ester of the acylamino acid and dimer diol of the present invention can be obtained, for example, by esterification or transesterification of dimer diol with an acyl amino acid such as an acyl neutral amino acid or acyl acidic amino acid as described above. The conditions for the esterification reaction are not particularly limited. In general, it is carried out by a commonly used method. For example, p-toluenesulfonic acid, sulfuric acid, hydrochloric acid, methanesulfonic acid, hydrogen fluoride or the like can be used as a catalyst, and benzene, toluene, xylene or the like can be used as a solvent at 50 ° C. to 200 ° C. Or it can carry out at 100-200 degreeC without a catalyst and a solvent. In the transesterification, alkali catalysts such as sodium hydroxide, potassium hydroxide and potassium carbonate, metal alkoxides such as sodium methoxide and the like can be used as catalysts. Moreover, regarding the order of the reaction process of an acylation reaction and an ester reaction, it is also possible to esterify an amino acid as a 1st step and to acylate as a 2nd step.

  When the amino acid of the acylamino acid is a neutral amino acid, in the esterification reaction, the esterification degree of the resulting ester can be arbitrarily adjusted between the monoester and the diester by changing the charging ratio of dimer diol and amino acid. . Depending on the purpose, the resulting ester may be a monoester or a diester, or a mixed ester made from two or more acylamino acids. Monoesters are slightly viscous at room temperature, but are less sticky, have a refreshing feel, and can provide an oily base with good emulsification stability for the ingredients. Furthermore, the cosmetics and external preparation which are excellent in the usability | use_condition, emulsification stability, etc. containing it can be provided. Diesters are higher in viscosity than monoester compounds at room temperature, and some of them are semi-transparent gels, but they are less sticky and have a refreshing feel, less skin irritation, and better emulsification stability over time. An oily base can be provided. Furthermore, the cosmetics and external preparation which are excellent in the usability | use_condition, emulsification stability, etc. containing it can be provided.

  When the amino acid of the acyl amino acid is an acidic amino acid, as in the case of the neutral amino acid, in the esterification reaction, the degree of esterification of the resulting ester can be arbitrarily adjusted by changing the charging ratio of dimer diol and acyl amino acid. However, when the amino acid is a dicarboxylic acid such as glutamic acid, an oligomer ester is formed by the diol and the dicarboxylic acid, and the viscosity tends to increase as compared with the case of a neutral amino acid. In the esterification reaction, the charging ratio is preferably 0.1 to 1.0 mol, more preferably 0.2 to 0.5 mol, of acylated acidic amino acid per mol of dimer diol. By setting such a ratio, an appropriate viscosity can be ensured.

  The resulting ester can be made into various types of ester compounds depending on the purpose of development, that is, selection of acyl group chain length, selection of amino acid type, selection of a combination of two or more different acyl amino acids, and dimer Esters having desired properties can be obtained by selecting raw materials such as diols. Industrial grade acylamino acids may contain small amounts of amino acids, fatty acids, acylpeptides and the like as impurities. Depending on the reaction conditions and the degree of purification, esters can be obtained in a form containing by-products, but they can be used as they are, and can be used for various purposes as they are, and further purified by ordinary methods as necessary. You can also.

Esters of acylamino acids, fatty acids and dimer diols can be selected by appropriately selecting their raw materials, viscosity, state (solid, soft wax, liquid, etc.), IOB value = (inorganic value / organic value), other Compatibility (such as compatibility) with ingredients can be arbitrarily adjusted, and a cosmetic excellent in feeling in use, stability, and the like can be provided.
The ester can be produced, for example, as follows.
Charge dimer diol and acylamino acid, and / or acylamino acid and fatty acid, and preferably add, as a catalyst, for example, 1.0% of 50% sulfuric acid aqueous solution, The reaction is raised to 130 ° C. Sampling is performed after several hours of reaction time, 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.

  In the context of the present invention, the esters are used as oily bases for cosmetics and external preparations. That is, the oily base of the present invention is cleansing oil, cleansing liquid, cleansing foam, cleansing cream, cleansing milk, cleansing gel, cleansing tissue, massage cream, massage milk, cold cream, emollient cream, emollient milk, moisture cream, moisture milk. , 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 shaving cream, sunscreen cream, sunscreen lotion, sunscreen oil, hair restorer, hair nourishing agent, bath preparation, pharmaceutical composition for external use, etc. It can be used as an oily base when preparing cosmetics and external preparations. There are no particular restrictions on the dosage forms of cosmetics and external preparations, and any emulsification system, solution system, solubilization system, powder dispersion system, water-oil two-layer system, water-oil-powder three-layer system, etc. It may be a dosage form.

  Although the compounding quantity of the ester compound regarding this invention to cosmetics and an external preparation is not specifically limited, 0.1-60 weight% is preferable with respect to the whole quantity of cosmetics or an external preparation, 1-20 weight% is still more preferable. .

  In addition to the oily base of the present invention, other oily bases can be blended in the cosmetic and external preparations of the present invention. Examples of such oily bases include liquid paraffin, solid paraffin, petrolatum, Raw materials derived from petroleum and minerals such as microcrystalline wax, ceresin, polyisobutene, isopropyl myristate, cetyl octanoate, octyldodecyl myristate, jojoba oil, whale wax, beeswax and other synthetic waxes and animal and plant waxes, olive oil, castor oil, Macadamia nut oil, sesame oil, cacao oil, mink oil, tree wax, candelilla wax, trioctanoic acid glycerin, tri (caproic acid, caprylic acid, capric acid) glycerin, etc. Alcohol, hexadecylua Synthetic and animal and plant-derived higher alcohols such as chol, isostearyl alcohol, octyldodecyl alcohol, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, ricinoleic acid, hydroxystearic acid, isostearic acid Synthesis of acids, isopalmitic acid, etc., and higher fatty acids derived from animals and plants, octyldodecyl pyrrolidonecarboxylate, dihexyldecyl lauroylglutamate, dioctyldecyl lauroylglutamate, dicetyl lauroylglutamate, dilauroylglutamate (phytosteryl / octyldodecyl), myristoylmethylaminopropydecylate Synthesis of hexyldecyl, lauroyl sarcosine isopropyl, etc., and amino acid oil phase raw materials derived from animals and plants, methylpolysiloxane, poly Xylethylene / methylpolysiloxane, polyoxypropylene / methylpolysiloxane, poly (polyoxyethylene / polyoxypropylene) methylpolysiloxane, methylphenylpolysiloxane, fatty acid-modified polysiloxane, aliphatic alcohol-modified polysiloxane, amino acid-modified polysiloxane, etc. Examples of silicones such as silicone polymers, and those usually used as oil components such as resin acids, esters, and ketones. Such an oily base can be optionally used in combination as long as the effect of the oily base of the present invention is not impaired. In the cosmetics and external preparations of the present invention, the oily base of the present invention is usually blended in an amount of 0.1 to 80% by weight, preferably 1 to 50% by weight, based on the total oily base.

In addition, the cosmetics and external preparations of the present invention include N-long chain acyl acidic amino acid salts, N-long chain acyl neutral amino acid salts, and the like as surfactants, as long as the effects of the ester relating to the present invention are not impaired. N-long chain acyl amino acid salt, N-long chain fatty acid acyl-N-methyl taurate salt, alkyl sulfate and alkylene oxide adduct, fatty acid amide ether sulfate, fatty acid metal salt and weak base, sulfosuccinic acid surfactant, alkyl Phosphates and their alkylene oxide adducts, anionic surfactants such as alkyl ether carboxylic acids, ether type nonionic surfactants such as higher alcohols and their alkylene oxide adducts, glycerin esters, sorbitan esters and their alkylene oxide adducts, etc. Ether ester type nonionic surface activity Agent, polyoxyalkylene fatty acid ester, glycerin ester, fatty acid polyglycerin ester, N-long chain acyl peptide polyglycerin, sorbitan ester, ester type surfactant such as sucrose fatty acid ester, alkyl glucoside, hydrogenated castor oil isostearic acid pyro Glutamic acid diester and its ethylene oxide adduct, and nitrogen-containing nonionic surfactants such as fatty acid alkanolamides, aliphatic amine salts such as alkylammonium chloride and dialkylammonium chloride, quaternary ammonium salts thereof, benzalkonium and the like Cationic surfactants such as aromatic quaternary ammonium salts and fatty acyl arginine esters, betaine surfactants such as carboxybetaine, aminocarboxylic acid type surfactants Agents, imidazoline-type amphoteric surfactant, various surfactants and the like, can be used in combination blended with oil base of the present invention.
The blending amount is 0.1 to 60% by weight, preferably 1 to 20% by weight, based on the total amount of the cosmetic and the external preparation.

Furthermore, the cosmetics and external preparations of the present invention include glycine, alanine, serine, threonine, arginine, glutamic acid, aspartic acid, leucine, valine and other amino acids, ethylene glycol, propylene glycol, 1,3-butylene glycol, dipropylene glycol, polyhydric alcohols such as glycerin, sorbitol, xylitol, polyamino acids including polyglutamic acid, polyaspartic acid and salts thereof, polyethylene glycol, arabic gums, alginates, xanthan gum, hyaluronic acid , Hyaluronate, chitin, water-soluble chitin, carboxyvinyl polymer, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropyltrimethylammonium chloride, polychlorinated Water-soluble polymers such as methylmethylenepiperidinium, polyvinylpyrrolidone derivatives, quaternary ammonium, cationized proteins, collagen degradation products and derivatives thereof, acylated proteins, polyglycerols, amino acid polyglycerol esters, sugar alcohols such as mannitol and the like An alkylene oxide adduct and lower alcohols such as ethanol and propanol can be blended.
The blending amount is 0.1 to 60% by weight, preferably 1 to 20% by weight, based on the total amount of the cosmetic and the external preparation.

  As preservatives, phenols, benzoic acid and salts thereof, halogenated bisphenols, acid amides, and quaternary ammonium salts can be blended. As a disinfectant, trichlorocarbanyl, zinc pyridione, benzalkonium chloride, chlorhexidine, halocarban, hinokitiol, phenol, isopropylphenol, photosensitizers and the like can be blended. As a chelating agent, edetate, sodium oxalate and the like can be blended. Citric acid, succinic acid, hydrochloric acid, ethanolamine, diethanolamine, triethanolamine, aqueous ammonia, sodium hydroxide, sodium chloride and the like can be blended as a pH adjuster. As UV inhibitors, benzophenone derivatives, paraaminobenzoic acid derivatives, paramethoxycinnamic acid derivatives, salicylic acid derivatives, dimethoxybenzylidene dioxoimidazolidine propionate octyl, urocanic acid, ethyl urocanate, 4-tert-butyl-4'-methoxydi Benzoylmethane, methyl anthranilate, rutin and its derivatives can be blended. As a whitening agent, kojic acid, arbutin, ascorbic acid, ascorbic acid glucoside, glutathione, ellagic acid, placenta extract, oryzanol, lucinol and the like can be blended.

  Furthermore, the cosmetics and external preparations of the present invention can be blended with components according to the intended cosmetics and external preparations. Examples of such components include fragrances, pigments, pearlizing agents, anti-inflammatory agents, analgesics, antifungal agents, hair restorers, antiperspirants, vitamin agents, hormone agents, viscosity modifiers, herbal medicines and the like. .

  EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to these Examples.

Example 1: Synthesis of mono (lauroylsarcosine) dimer diol ester;
Dimer diol (compound name: dimer linoleyl alcohol “Pripol 2033” manufactured by Unikema, in Examples 1 to 15, this product was used for dimer diol synthesis) 1072 g and lauroyl sarcosine 528 g were charged. Stir, add 16 ml of 50% sulfuric acid aqueous solution, raise the temperature to 130 ° C. while flowing nitrogen, and react. Sampling was performed after 3 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 1536 g (yield 96%) of the product.

  As a result of analysis of this product, acid value = 0.74, saponification value = 70.1 (theoretical value = 71.1), hydroxyl value = 70.09 (theoretical value = 71.1), IOB value = 0. .36 compounds.

Per the ester compound, as a result of infrared absorption spectrum measurement, the wavelength 3471cm ^-1 (hydroxyl group) showed characteristic absorption at 1750 cm ^-1 (ester) and 1658 cm ^-1 (amide).

Example 2: Synthesis of sesqui (lauroylsarcosine) dimer diol ester;
915 g of dimer diol (Pripol 2033: made by Unikema) and 685 g of lauroyl sarcosine are charged and stirred, and 16 ml of 50% sulfuric acid aqueous solution is added, and the temperature is raised to 130 ° C. while introducing nitrogen, and the reaction is carried out. 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 1520 g of product (yield 95%).

  As a result of analysis of the product, acid value = 1.05, saponification value = 93.8 (theoretical value = 92.0), hydroxyl value = 27.35 (theoretical value = 30.6), IOB value = 0. .38 compounds.

Per the ester compound, as a result of infrared absorption spectrum measurement, the wavelength 3471cm ^-1 (hydroxyl group) showed characteristic absorption at 1750 cm ^-1 (ester) and 1660 cm ^-1 (amide).

Example 3: Synthesis of di (lauroylsarcosine) dimer diol ester;
864 g of dimer diol (Pripol 2033: made by Unikema) and 736 g of lauroyl sarcosine are charged and stirred, and 16 ml of 50% sulfuric acid aqueous solution is added, and the temperature is raised to 130 ° C. while introducing nitrogen, and the reaction is carried out. 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 g (yield 93%) of the product.

  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 this ester compound, characteristic absorption was observed at wavelengths of 1750 cm ⁻¹ (ester) and 1658 cm ⁻¹ (amide).

Example 4: Synthesis of di (lauroylsarcosine / isostearic acid) dimer diol ester;
824 g of dimer diol (Pripol 2033: made by Unikema), 374 g of lauroyl sarcosine and 402 g of isostearic acid are charged, stirred, and 16 ml of 50% sulfuric acid aqueous solution is added, and the temperature is raised to 130 ° C. while flowing in nitrogen, and the reaction is carried out. 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 1536 g of the product (yield 96%).

  As a result of analysis of this product, it was a compound having an acid value = 1.34, a saponification value = 107.00 (theoretical value = 106.37), and an IOB value = 0.24.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 1738 cm ⁻¹ (ester) and 1664 cm ⁻¹ (amide).

Example 5: Synthesis of mono (N-myristoyl-N-methyl-β-alanine) dimer diol ester;
Charge 1054 g of dimer diol (Pripol 2033: made by Unikema) and 546 g of N-myristoyl-N-methyl-β-alanine, stir, add 16 ml of 50% sulfuric acid aqueous solution, and raise the temperature to 130 ° C. while introducing nitrogen. React. Sampling was performed after 3 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 1544 g (yield 96.5%) of the product.

  As a result of analysis of this product, acid value = 0.76, saponification value = 66.00 (theoretical value = 67.00), hydroxyl value = 72.22 (theoretical value = 67.00), IOB value = 0 .34 compounds.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 3445 cm ⁻¹ (hydroxyl group), 1737 cm ⁻¹ (ester) and 1655 cm ⁻¹ (amide).

Example 6: Synthesis of sesqui (N-myristoyl-N-methyl-β-alanine) dimer diol ester;
Dimer diol (Pripol 2033: made by Unikema) 861g, N-myristoyl-N-methyl-β-alanine 739g was charged and stirred, and 16ml of 50% sulfuric acid aqueous solution was added, and the temperature was raised to 130 ° C while introducing nitrogen. React. Sampling was performed after 3 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 1520 g (yield 95%) of the product.

  As a result of analysis of this product, acid value = 1.20, saponification value = 87.8 (theoretical value = 85.97), hydroxyl value = 26.05 (theoretical value = 28.50), IOB value = 0 .36 compounds.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 3445 cm ⁻¹ (hydroxyl group), 1737 cm ⁻¹ (ester) and 1655 cm ⁻¹ (amide).

Example 7: Synthesis of di (N-myristoyl-N-methyl-β-alanine) dimer diol ester;
Dimer diol (Pripol 2033: made by Unikema) 784g, N-myristoyl-N-methyl-β-alanine 816g was charged and stirred, 16ml of 50% sulfuric acid aqueous solution was added, and the temperature was raised to 130 ° C while introducing nitrogen. React. 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 1504 g of the product (yield 94%).

  As a result of analysis, the product was a compound having an acid value = 1.80, a saponification value = 98.42 (theoretical value = 99.66), and an IOB value = 0.39.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 1737 cm ⁻¹ (ester) and 1655 cm ⁻¹ (amide).

Example 8: Synthesis of di (N-myristoyl-N-methyl-β-alanine / isostearic acid) dimer diol ester;
Dimerdiol (Pripol 2033: made by Unikema) 776 g, N-myristoyl-N-methyl-β-alanine 432 g and isostearic acid 392 g were charged and stirred, and 16 ml of 50% sulfuric acid aqueous solution was added. Raise the reaction temperature to 0 ° C. 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 1521 g of the product (yield 95%).

  As a result of analysis, the product was a compound having an acid value = 1.40, a saponification value = 99.18 (theoretical value = 102.29), and an IOB value = 0.23.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 1737 cm ⁻¹ (ester) and 1656 cm ⁻¹ (amide).

Example 9: Synthesis of [lauroyl glutamic acid (0.5 mol) dimer diol (1 mol)] ester;
Dimer diol (Pripol 2033: made by Unikema) 1224 g and lauroyl glutamic acid 376 g are charged, stirred, and 16 ml of 50% sulfuric acid aqueous solution is added, and the temperature is raised to 130 ° C. while introducing nitrogen, and the reaction is carried out. Sampling was performed after 3 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 then subjected to precoat filtration to obtain 1472 g of a product (yield 92%).

  As a result of analysis, the product was a compound having an acid value = 0.74, a saponification value = 82.61 (theoretical value = 82.21), and an IOB value = 0.31.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 1738 cm ⁻¹ (ester) and 1657 cm ⁻¹ (amide).

Example 10: Synthesis of [lauroyl glutamic acid (0.5 mol) / isostearic acid (0.5 mol)] dimer diol (1 mol) ester;
1018 g of dimer diol (Pripol 2033: made by Unikema), 309 g of lauroyl glutamic acid, and 273 g of isostearic acid are charged and stirred, and 16 ml of 50% aqueous sulfuric acid solution is added, and the temperature is raised to 130 ° C. while allowing nitrogen to flow. Sampling was performed after 3 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 1536 g of product (yield 96%).

  As a result of analysis of this product, it was a compound having an acid value of 1.51, a saponification value of 103.1 (theoretical value = 102.89), and an IOB value of 0.27.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 1738.90 cm ⁻¹ (ester) and 1656 cm ⁻¹ (amide).

Example 11: Synthesis of [lauroyl glutamic acid (0.25 mol) / isostearic acid (0.5 mol)] dimer diol (1 mol) ester;
1127 g of dimer diol (Pripol 2033: made by Unikema), 171 g of lauroyl glutamic acid, and 302 g of isostearic acid are charged and stirred, and 16 ml of 50% aqueous sulfuric acid solution is added, and the temperature is raised to 130 ° C. while flowing in nitrogen. Sampling was performed after 3 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 1503 g of the product (yield 94%).

  As a result of analysis of the product, a compound having an acid value = 1.21, a saponification value = 75.5 (theoretical value = 75.00), and an IOB value = 0.26 was obtained.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 1738.90 cm ⁻¹ (ester) and 1657 cm ⁻¹ (amide).

Example 12: Synthesis of [lauroylglutamic acid (0.1 mol) / isostearic acid (0.9 mol)] dimer diol (1 mol) ester;
1058 g of dimer diol (Pripol 2033: made by Unikema), 32 g of lauroyl glutamic acid, and 510 g of isostearic acid are charged and stirred, and 16 ml of 50% aqueous sulfuric acid solution is added, and the temperature is raised to 130 ° C. while allowing nitrogen to flow. Sampling was performed after 3 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 1520 g (yield 95%) of the product.

  As a result of analysis of this product, it was a compound having an acid value = 1.37, a saponification value = 73.7 (theoretical value = 72.8), and an IOB value = 0.22.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 1738 cm ⁻¹ (ester) and 1658 cm ⁻¹ (amide).

Example 13: Synthesis of [lauroyl glutamic acid (0.3 mol) / lauroyl sarcosine (0.7 mol)] dimer diol (1 mol) ester;
1045 g of dimer diol (Pripol 2033: made by Unikema), 365 g of lauroyl sarcosine and 190 g of lauroyl glutamic acid are charged and stirred, and 16 ml of 50% aqueous sulfuric acid solution is added, and the temperature is raised to 130 ° C. while flowing nitrogen, and the reaction is carried out. Sampling was performed after 3 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 g (yield 93%) of the product.

  As a result of analysis, the product was a compound having an acid value = 2.5, a saponification value = 96.8 (theoretical value = 95.3), and an IOB value = 0.30.

Per the ester compound, as a result of infrared absorption spectrum measurement showed the characteristic absorption at a wavelength 1741cm ^-1 (ester) and 1660 cm ^-1 (amide).

Example 14: Synthesis of [lauroyl glutamic acid (0.3 mol) / N-myristoyl-N-methyl-β-alanine (0.7 mol)] dimer diol (1 mol) ester;
Dimer diol (Pripol 2033: made by Unikema) 1011 g, N-myristoyl-N-methyl-β-alanine 405 g, lauroyl glutamic acid 184 g was charged and stirred, and 16 ml of 50% sulfuric acid aqueous solution was added. Raise the reaction temperature to 0 ° C. Sampling was performed after 3 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 1504 g of the product (yield 94%).

  As a result of analysis of this product, it was a compound having an acid value of 2.6, a saponification value of 92.6 (theoretical value = 92.0), and an IOB value of 0.28.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 1737 cm ⁻¹ (ester) and 1651 cm ⁻¹ (amide).

Example 15: Synthesis of [N-myristoyl-N-methyl-β-alanine (0.5 mol) / lauroyl sarcosine (0.5 mol)] dimer diol (1 mol) ester;
Dimerdiol (Pripol 2033: made by Unikema) 1042 g, Lauroylsarcosine 261 g, N-myristoyl-N-methyl-β-alanine 297 g were charged and stirred, and 16 ml of 50% sulfuric acid aqueous solution was added. The reaction is raised to 130 ° C. Sampling was performed after 3 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 then subjected to precoat filtration to obtain 1472 g of a product (yield 92%).

  As a result of analysis of this product, it was a compound having an acid value = 2.00, a saponification value = 72.5 (theoretical value = 72.1), and an IOB value = 0.32.

As a result of measuring the infrared absorption spectrum of this ester compound, characteristic absorption was observed at wavelengths of 1738 cm ⁻¹ (ester) and 1651 cm ⁻¹ (amide).

  Hereafter, the effect of the oil-based base which mix | blended one or more ester regarding this invention with a compounding example is evaluated, and the result is shown.

Examples 16 and 17 and Comparative Examples 1 to 7 (dispersion performance test of titanium oxide)
Table 1 below shows the results of a dispersion performance test of titanium oxide using di (myristoyl-N-methyl-β-alanine) dimer diol ester or lauroyl glutamic acid dimer diol ester obtained in Examples.

  Titanium oxide using the esters described in Examples 7 and 9 and the general oily bases shown in the comparative examples, isopropyl myristate, cetyl octanoate, tri (capryl / caprin) glyceryl, trioctanoin, and squalane. The dispersion performance test was conducted. The measuring method was performed by stirring each base and 20% titanium oxide with a disper mixer for 3 minutes, transferring to a 100 ml graduated cylinder, and measuring the height of precipitated titanium oxide. The results are as shown in Table 1.

  As a result, the general oil bases of Comparative Examples 1 to 5 showed an average of 51.6% separation in 3 days, and the isostearic acid dimer diol ester compounds of Comparative Examples 6 and 7 averaged 7.05% in 3 days. However, the ester compounds of Examples 16 and 17 of the present invention did not separate at all in 3 days, and showed excellent performance in pigment dispersibility.

Example 18: (W / O foundation cream)
Using the ester described in Example 7 and the ester compound that is a general oil base shown in Comparative Examples, W / O foundation creams having the formulations shown in Table 3 below were prepared. The method for preparing these W / O foundation creams is as follows. That is, components 1 and 2 were each heated to 70 ° C., and component 2 was gradually added and emulsified while stirring component 1. Next, it cooled and added the component 3 at 50 degreeC, and cooled to 30 degreeC.

  These W / O foundation 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 criteria for determining the emulsion stability were ○ if it was stable at 40 ° C. for 1 month, and × if it was separated in 1 month.

  The sensory evaluation criteria are shown in Table 2.

Example 19 (base cream)
A base cream having the composition shown in Table 4 below was prepared as follows. That is, component 1 and component 2 were each heated to 60 ° C., and component 2 was gradually added while stirring component 1. Next, it cooled and added the component 3 at 50 degreeC, and cooled to 30 degreeC. This base cream is excellent in pigment dispersibility, so it has improved familiarity with the foundation, has a good foundation, has a good feel, and has a dry feel. Furthermore, it has excellent familiarity and emollient functionality. .

Example 20 (emollient skin lotion)
An emollient skin lotion having the composition shown in Table 5 below was prepared as follows. That is, component 1 and component 2 were each heated to 70 ° C., and component 1 was gradually added while stirring component 2. Next, it cooled and added the component 3 at 40 degreeC, and cooled to 30 degreeC. This emollient skin lotion exhibited a sensuality excellent in spreading, familiarity and emollient.

Example 21 (W / O-emollient cream)
W / O-emollient creams having the compositions shown in Table 6 below were prepared as follows. That is, component 1 and component 2 were each heated to 60 ° C., and component 2 was gradually added while stirring component 1. Next, it cooled and added the component 3 at 50 degreeC, and cooled to 30 degreeC. This W / O-emollient cream exhibited a sensuality excellent in the effect of imparting good spread, good familiarity and moist feeling.

Example 22 (W / O-emollient emulsion)
W / O-emollient emulsions having the compositions shown in Table 7 below were prepared as follows. That is, component 1 and component 2 were dissolved at room temperature, and component 2 was gradually added while stirring component 1. This W / O-emollient emulsion exhibited a good sensory effect in the effect of imparting good spread, good familiarity and moist feeling.

Example 23 (O / W-Moisture Cream)
O / W-moisture creams having the compositions shown in Table 8 below were prepared as follows. That is, component 1 and component 2 were each heated to 70 ° C., and component 2 was gradually added while stirring component 1. Next, it cooled and added the component 3 at 50 degreeC, and cooled to 30 degreeC. This O / W-moisture cream had a glossy and sensation, and showed a good sensory and emollient sensuality.

Example 24 (O / W-moisture emulsion)
O / W-moisture emulsions having the compositions shown in Table 9 below were prepared as follows. That is, component 1, component 2 and component 3 were each heated to 70 ° C., and component 1 and component 3 were gradually added while stirring component 2. Next, it cooled to 30 degreeC. This O / W-moisture emulsion showed a sensuality that was excellent in spreading, familiarity and emollient.

Example 25 (massage cream)
A massage cream having the composition shown in Table 10 below was prepared as follows. That is, component 1 and component 2 were each heated to 70 ° C., and component 2 was gradually added while stirring component 1. Next, it cooled and added the component 3 at 50 degreeC, and cooled to 30 degreeC. This massage cream exhibited a sensuality that was excellent in spreading, familiarity and moist feeling.

Example 26 (UV-cream)
UV-creams having the compositions shown in Table 11 below were prepared as follows. That is, component 1 and component 2 were each heated to 70 ° C., and component 2 was gradually added while stirring component 1. Next, the mixture was cooled, added with component 3 at 45 ° C., and cooled to 30 ° C. This UV-cream suppresses breakage due to sweat and the like, and exhibits excellent sensation in pigment dispersibility and familiarity.

Example 27 (UV-lotion)
UV-lotions having the compositions shown in Table 12 below were prepared as follows. That is, component 1 and component 2 were stirred and dissolved at room temperature, and component 2 and component 3 were gradually added while stirring component 1. This UV-lotion suppressed breakage due to sweat and the like, and showed excellent sensation in pigment dispersibility and familiarity.

Example 28 (lipstick)
Lipsticks having the compositions shown in Table 13 below were prepared as follows. That is, component 1 was heated and dissolved, component 2 was added thereto, kneaded with a roll mill, uniformly dispersed, defoamed, poured into a mold, rapidly cooled, and formed into a stick shape. This lipstick had a good sensation with a good fit with the skin and good spreadability.

Example 29 (Rinse)
A rinse having the composition shown in Table 14 below was prepared as follows. That is, component 1 and component 2 were each heated to 80 ° C., and component 1 was gradually added while stirring component 2. Next, it cooled and added the component 3 at 50 degreeC, and cooled to 30 degreeC. This rinse did not become sticky, gave the hair a moist feeling and gloss, and showed excellent sensuality as a smooth finger.

Example 30 (hair conditioner)
A hair conditioner having the composition shown in Table 15 below was prepared as follows. That is, component 1 and component 2 were each heated to 80 ° C., and component 1 was gradually added while stirring component 2. Next, the mixture was cooled, added with component 3 at 45 ° C., and cooled to 30 ° C. This hair conditioner kept the moisture of the hair, imparted gloss and moist feeling, and exhibited excellent sensuality as a smooth finger.

Example 31 (hair cream)
A hair cream having the composition shown in Table 16 below was prepared as follows. That is, component 1 and component 2 were each heated to 70 ° C., and component 2 was gradually added while stirring component 1. Next, the mixture was cooled, added with component 3 at 45 ° C., and cooled to 30 ° C. This hair cream was glossy, non-sticky, kept moisture on the hair, and exhibited an excellent sensory feel.

Example 32 (cleansing oil)
Cleansing oils having the compositions shown in Table 17 below were prepared as follows. That is, component 1 and component 2 were dissolved at room temperature, and component 2 was gradually added while stirring component 1. This cleansing oil was familiar with foundations, makeup, etc., and exhibited a sensuality excellent in cleansing performance.

Example 33 (Washburg cleansing oil)
Washable cleansing oil having the composition shown in Table 18 below was prepared as follows. That is, component 1 and component 2 were each heated to 60 ° C., and component 2 was gradually added while stirring component 1. Next, the mixture was cooled, added with component 3 at 35 ° C., and cooled to 30 ° C. This washable cleansing oil has a characteristic that it is viscous and difficult to sag during use, is well-familiar with makeup, has excellent cleansing performance, and has a refreshed feeling after use.

Example 34 (cleansing gel)
Cleansing gels having the compositions shown in Table 19 below were prepared as follows. That is, component 1 and component 2 are each stirred and dissolved at room temperature, and component 3 is added to component 2 and stirred and dissolved. Component 1 was gradually added while stirring component 2 + component 3. Since this cleansing gel was excellent in pigment dispersibility, it was well suited to foundations, makeup, etc., and exhibited excellent cleansing performance.

Claims (3)

An oily base containing an ester of an acyl amino acid and a dimer diol and / or an ester of an acyl amino acid, a fatty acid and a dimer diol ,
The amino acid of the acyl amino acid is an amino acid selected from glycine, alanine, threonine, β-alanine, sarcosine, N-methyl-β-alanine, aminobutyric acid, glutamic acid, aspartic acid,
The acyl group of the acylamino acid has 12 to 26 carbon atoms,
The oil-based base whose carbon number of dimer diol is 22-44 .   The oily base according to claim 1, wherein the fatty acid has 2 to 26 carbon atoms. A cosmetic or external preparation comprising the oily base according to claim 1 or 2 .