JP2022129583A - Polyglyceryl fatty acid ester, feeling regulator and cosmetic - Google Patents

Abstract

To provide a polyglyceryl fatty acid ester capable of acquiring cosmetic which is excellent in use feeling relative to prior arts.SOLUTION: There is provided a polyglyceryl fatty acid ester in which, a hydroxyl value of polyglycerol is 1400 or lower, a constituent fatty acid is at least one kind or more kinds selected from a monocarboxylic acid and a derivative thereof, and at least one kind or more kinds selected from a polycarboxylic acid and a derivative thereof, an esterification ratio of whole constituent fatty acid to the polyglyceryl is 30-70%, an esterification ratio of the polycarboxylic acid and the derivative thereof to the polyglyceryl is 2-8%, and a loss elastic modulus of a composition which is added to fluid paraffin by 5%, is vibration strain of 1% or more and stress of 5000 Pa or more at a maximum point.SELECTED DRAWING: None

Description

TECHNICAL FIELD The present invention relates to polyglycerol fatty acid esters, texture modifiers and cosmetics.

Polyglycerin fatty acid esters are known ingredients such as surfactants and oil gelling agents, and are widely used in the fields of foods and cosmetics. In such polyglycerol fatty acid esters, there are many compounds with the same name but different structures depending on the selection of raw materials to be used, the blending amount, etc., and the difference in the structures causes different properties.

In Patent Documents 1 and 2, various glycerin fatty acid esters and polyglycerin fatty acid esters have been studied, and their performance as raw materials for cosmetics has also been studied. In Patent Document 1, a gel-like substance is visually evaluated when an esterification product is dissolved in oil, and in Patent Document 2, a gel-like substance is visually evaluated when an esterified product is dissolved in alcohol. are performing performance evaluations.

In recent years, dynamic viscoelasticity analysis has also been conducted for cosmetic raw materials. This is for predicting the feeling of using cosmetics by analyzing the behavior when strain is applied. Based on these analyses, attempts have been made to produce cosmetics with a more excellent feeling in use than in the past and cosmetic raw materials that give such cosmetics.

On the other hand, polyglycerin fatty acid esters such as those described above have not been studied as such, and have not been studied as ingredients for adjusting the feel of cosmetics when used.

Patent No. 2700377 Patent No. 3535197

An object of the present invention is to provide a polyglycerol fatty acid ester that can be used to obtain a cosmetic having a superior feel when used.

In the present invention, the polyglycerin has a hydroxyl value of 1400 or less,
The constituent fatty acids are at least one selected from the group consisting of monocarboxylic acids and derivatives thereof, and at least one selected from the group consisting of polycarboxylic acids and derivatives thereof,
The esterification rate of all constituent fatty acids with respect to the polyglycerin is 30 to 70%,
The esterification rate of the polycarboxylic acid and its derivative with respect to the polyglycerol is 2 to 8%,
The polyglycerin fatty acid ester is characterized in that the loss elastic modulus of a composition obtained by adding 5% to liquid paraffin is 1% or more in vibrational strain and 5000 Pa or more in stress at the maximum point.

Preferably, the monocarboxylic acid is behenic acid.
Preferably, the polycarboxylic acid is eicosanedioic acid.
The present invention is also a feel modifier comprising the polyglycerin fatty acid ester.
The present invention is also a cosmetic containing the polyglycerin fatty acid ester and an oily component.
The oily component is preferably one or more selected from the group consisting of hydrocarbon oils and ester oils.
It is preferable that the amount of the polyglycerol fatty acid ester blended in the cosmetic is 0.01 to 20% by mass relative to the total amount of components other than water in the cosmetic.

The polyglycerin fatty acid ester of the present invention has excellent properties, particularly in improving the feeling of use when blended in cosmetics.

4 is a graph of loss modulus of a composition obtained by adding 5% of Synthesis Example 1 to liquid paraffin.

The present invention will be described in detail below.
Polyglycerin fatty acid esters are well-known compounds and are often used ingredients in the field of cosmetics.

Polyglycerin fatty acid ester is a compound having a complicated structure, and an extremely large number of structures are conceivable depending on the degree of polymerization, esterification rate, and the like of polyglycerin. This chemical structure changes the physical properties.

Polyglycerol fatty acid esters are commonly used as gelling agents for oils. Therefore, it is very important as a component for adjusting physical properties. Since cosmetics are used by being applied to the skin, they are required to have properties such as feel, spreadability, and the like upon application. These feeling during use are also considered to be very important properties in cosmetics, and many attempts have been made to improve this.

In recent years, attempts have been made to verify the feeling of use of such cosmetics by not only monitoring tests based on user evaluations, but also by measuring physical properties, and to develop raw materials with even better performance in the field of cosmetics. It is done.

The present inventors have investigated the dynamic viscoelasticity of a composition containing a polyglycerol fatty acid ester and an oil, and have found a composition that gives a particularly excellent feel when used as a cosmetic raw material. We examined what it is.

As a result of manufacturing many types of polyglycerol fatty acid esters and confirming their performance, the hydroxyl value of polyglycerin is 1400 or less, the esterification rate is 30 to 70%, and the loss of the composition added by 5% to liquid paraffin The inventors have found that a polyglycerin fatty acid ester having a vibration strain of 1% or more and a stress of 5000 Pa or more at the maximum point of elastic modulus can provide cosmetics with an excellent feeling of use, and have completed the present invention.

In other words, from the viewpoint of the feeling of use of cosmetics, regarding the transition of the loss modulus obtained when stress is gradually applied by dynamic viscoelasticity, the strain stress until reaching the maximum point is large, and the value is also high. When used as a cosmetic, the composition having such properties is excellent in feeling of use from the viewpoint of obtaining a smooth feel when it is spread on the skin. Therefore, a polyglycerin fatty acid ester having such properties can provide an unprecedented excellent feeling in use.

(About dynamic viscoelasticity measurement)
In the present specification, the dynamic viscoelasticity measurement was performed according to the following procedure using the following equipment.
Sample to be measured: Composition in which 5 wt% of polyglycerol fatty acid ester is added to liquid paraffin Equipment used: Dynamic viscoelasticity measuring device (Discovery Hybrid Rheometer-2 manufactured by TA instruments)
Measurement jig: diameter 40 mm Parallel plate A composition obtained by adding 5 wt% of polyglycerin fatty acid ester to liquid paraffin and uniformly mixing it is measured at a temperature of 20 ° C., a frequency of 10 radians per second, and a gap width of 500 μm. The viscoelasticity was measured while gradually increasing from 0.01% to 100% to measure the transition of the loss elastic modulus. When the results are graphed as shown in FIG. 1, the vibration strain at the maximum point is 1% or more and the stress is 5000 Pa or more.

A composition of polyglycerol fatty acid ester that satisfies such a value improves the spreadability and massaging properties during application due to the action of maintaining high viscosity when spread, and provides a composition with excellent usability. can be inferred.
When the vibration strain at the maximum point of the loss elastic modulus is 1% or more, the spreadability at the time of application is improved, so that the feeling of use is excellent. The stress at the maximum point of the loss elastic modulus is 5000 Pa or more, which improves the massage properties during application, and thus provides an excellent feel during use.

(Regarding the chemical structure of polyglycerin fatty acid ester)
As described above, the polyglycerol fatty acid ester can be changed relatively freely in its chemical structure, degree of esterification, and the like. Under such circumstances, polyglycerin fatty acid esters that can be suitably used for the purpose of the present invention are polyglycerin having a hydroxyl value of 1400 or less and an esterification rate of 30 to 70%.

The hydroxyl value in the present invention is a numerical value that serves as an index of the number of hydroxyl groups contained in polyglycerol, and is required to neutralize the acetic acid required to acetylate the free hydroxyl groups contained in 1 g of polyglycerol. Milligrams of potassium hydroxide. The number of milligrams of potassium hydroxide is calculated according to the Japan Oil Chemists' Society compilation, "Japan Oil Chemists' Society Establishment, Standard Oil Analysis Test Method, 2013 Edition".
The hydroxyl value of the polyglycerin may be calculated from the polyglycerin as a raw material, or may be calculated from the polyglycerin obtained by saponifying and decomposing the polyglycerin fatty acid ester of the present invention.
If the hydroxyl value exceeds 1,400, it is not preferable in that it does not exhibit functions that provide excellent feeling during use. Although the upper limit of the hydroxyl value is not particularly limited, it is preferably 950, and most preferably 870, from the viewpoint of providing a better feel during use.

The lower limit of the hydroxyl value is more preferably 800, and most preferably 830, from the viewpoint of providing a better feel during use.

The polyglycerol fatty acid ester of the present invention has an esterification rate of 30 to 70%. The esterification rate is calculated from the average degree of polymerization of polyglycerin (n) calculated from the hydroxyl value by terminal group analysis, the number of hydroxyl groups possessed by this polyglycerin (n+2), and the number of moles of fatty acid added to polyglycerin (M ), then
Esterification rate (%) = (M / (n + 2)) x 100
It is a value calculated by Here, the average degree of polymerization (n) is calculated by the following formula from the hydroxyl value obtained by terminal group analysis.
molecular weight = 74n + 18
If the hydroxyl value=56110(n+2)/molecular weight esterification rate is too low, the compatibility with the oily base may be lost, resulting in the problem of precipitation. If the esterification rate is too high, the esterification reaction will be difficult to proceed, making it difficult to obtain the polyglycerin fatty acid ester.

The lower limit of the esterification rate is more preferably 40% from the viewpoint of providing a more excellent feel during use. The upper limit of the esterification rate is more preferably 60% from the viewpoint of providing a more excellent feel during use.

The polyglycerol fatty acid ester of the present invention has a polyglycerol unit and a fatty acid unit as structural units, which are linked by an ester bond.
A polyglycerin unit as a structural unit is a compound in which two or more glycerins are condensed. More preferably, 3 or more are condensed, and 6 or more are more preferably condensed.

In addition, the present invention relates to "polyglycerin fatty acid ester", not glycerin fatty acid ester. However, as described above, the constitutional unit of polyglycerin may be a mixture of a plurality of components having different condensation numbers, and glycerin may be included as one of such mixed components.

The fatty acid is not particularly limited, and examples thereof include caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, ricinoleic acid, palmitoleic acid, isooctyl acid (2-ethyl hexanoic acid, etc.), isononanoic acid (3,5,5-trimethylhexanoic acid, etc.), isopalmitic acid, isostearic acid (2-heptylundecanoic acid, polymethyl-branched type manufactured by Emery, etc.), cerotic acid, montanic acid , Monocarboxylic acids such as melissic acid, succinic acid, citric acid, adipic acid, sebacic acid, eicosanedioic acid, dodecanedioic acid, 1,10-decamethylenedioic acid, 1,12-dodecamethylenedioic acid, 1,15- Polycarboxylic acids such as pentadecamethylenedioic acid, 1,28-octacosamethylenedioic acid, and 1,7-ethyloctadecanedioic acid can be mentioned, and two or more of these are used in combination.

The above monocarboxylic acid and polycarboxylic acid may be derivatives. Derivatives include these acid anhydrides and acid halides.

Among these, at least one selected from the group consisting of monocarboxylic acids and derivatives thereof and at least one selected from the group consisting of polycarboxylic acids and derivatives thereof are used in combination. preferable. Moreover, it is particularly preferable to use a linear and saturated monocarboxylic acid as the monocarboxylic acid, and a saturated dicarboxylic acid as the polycarboxylic acid. A mixture of these two kinds of acids is preferable in terms of exhibiting a function with excellent feeling in use.

In the polyglycerol fatty acid ester of the present invention, when a dibasic acid such as eicosanedioic acid is used as the polycarboxylic acid, the esterification rate of the dibasic acid is not particularly limited, but the esterification rate is 2 to 2. It is preferably 8%, more preferably 3-7%.
If the dibasic acid esterification rate is in the range of 2 to 8%, the cross-linking reaction of the polyglycerin fatty acid ester can be appropriately controlled, and the desired polyglycerin fatty acid ester can be obtained. Also, the dispersibility when added to an oil agent is improved.

The polyglycerin fatty acid ester of the present invention can be obtained by a known general production method without any limitation on its production method.

The polyglycerol fatty acid ester of the present invention can be suitably used as a feel modifier in the field of cosmetics. That is, by blending the above-mentioned polyglycerin fatty acid ester, it is possible to improve the feel of the cosmetic during use.

The present invention is also a cosmetic containing the polyglycerin fatty acid ester.
Polyglycerol fatty acid esters are known as ingredients in cosmetics. The polyglycerin fatty acid ester of the present invention can also be used in similar applications.

The cosmetic of the present invention preferably contains the polyglycerol fatty acid ester of the present invention in a proportion of 0.01 to 20.0% by mass relative to the total amount of ingredients other than water in the cosmetic. . By blending within such a range, it is preferable in that a particularly excellent feeling of use can be obtained. The above lower limit is more preferably 0.05% by mass, and even more preferably 0.1% by mass. The upper limit is more preferably 15.0% by mass, and even more preferably 10.0% by mass. In addition, the above description does not mean that the cosmetic contains water as an essential component, and the cosmetic of the present invention may not contain water. In the case of a cosmetic that does not contain water, it is preferable to contain the polyglycerin fatty acid of the present invention within the above range with respect to the total amount of the cosmetic.

Cosmetics are not particularly limited, and creams such as lipsticks, lip glosses, lip balms, hand creams, beauty creams, hair creams, serums, milky lotions, lotions, foundations, controls, sunscreens (sunscreen cosmetics), and blushers. , foundation cosmetics, eye shadows, eyebrows, mascara, shampoos, rinses, conditioners, cleansers, hair styling agents, nail beauty agents, and the like. In particular, it can be suitably used for lip cosmetics such as lipstick and lip gloss.

In addition to the above polyglycerin fatty acid ester, the cosmetic of the present invention can also use general raw materials used in the field of cosmetics.

The cosmetic composition of the present invention may optionally contain water and usually added ingredients such as oily base materials, alcohols, moisturizing agents, polymers/thickening/gelling agents, antioxidants, preservatives, and bactericides. , chelating agent, pH adjuster/acid/alkali, ultraviolet absorber, whitening agent, solvent, exfoliating/dissolving agent, antipruritic agent, anti-inflammatory agent, antiperspirant, cooling agent, reducing agent/oxidizing agent, vitamins and their Derivatives, sugars and their derivatives, organic acids, perfumes, etc. can be blended. The cosmetic of the present invention can be particularly preferably used as an oily cosmetic containing the above oily base as an essential component.

Examples of these additive components include higher alcohols such as cetanol, myristyl alcohol, oleyl alcohol, lauryl alcohol, cetostearyl alcohol, stearyl alcohol, arachyl alcohol, behenyl alcohol, jojoba alcohol, chimyl alcohol, and batyl alcohol. alcohol, hexyl decanol, isostearyl alcohol, 2-octyldodecanol, dimer diol and the like. Also coconut oil, palm oil, palm kernel oil, safflower oil, olive oil, castor oil, avocado oil, sesame oil, tea oil, evening primrose oil, wheat germ oil, macadamia nut oil, hazelnut oil, kukui nut oil, rosehip oil, meadow Foam oil, persic oil, tea tree oil, peppermint oil, corn oil, rapeseed oil, sunflower oil, wheat germ oil, linseed oil, cottonseed oil, soybean oil, peanut oil, rice bran oil, cocoa butter, shea butter, hydrogenated coconut oil, Vegetable oils and fats such as hydrogenated castor oil, jojoba oil and hydrogenated jojoba oil; animal fats and oils such as beef tallow, milk fat, horse fat, egg yolk oil, mink oil and turtle oil; phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, sphingo Phospholipids such as myelin, phosphatidic acid and lysolecithin; Phospholipid derivatives such as hydrogenated soybean phospholipids and hydrogenated egg yolk phospholipids; Sterols such as cholesterol, dihydrocholesterol, lanosterol, dihydrolanosterol and phytosterol; cholesteryl acid, cholesteryl stearate, cholesteryl isostearate, cholesteryl oleate, di(cholesteryl/behenyl/octyldodecyl) N-lauroyl-L-glutamate, di(cholesteryl/octyldodecyl) N-lauroyl-L-glutamate, N-lauroyl - di(phytosteryl/behenyl/octyldodecyl) L-glutamate, di(phytosteryl/octyldodecyl) N-lauroyl-L-glutamate, cholesteryl 12-hydroxystearate, cholesteryl macadamia nut oil fatty acid, phytosteryl macadamia nut oil fatty acid, phytosteryl isostearate, Sterol esters such as soft lanolin fatty acid cholesteryl, hard lanolin fatty acid cholesteryl, long-chain branched fatty acid cholesteryl, long-chain α-hydroxy fatty acid cholesteryl; ethyl oleate, avocado oil fatty acid ethyl, isopropyl myristate, isopropyl palmitate, octyl palmitate, Lower alcohol fatty acid esters such as isopropyl isostearate, isopropyl lanolin fatty acid, diethyl sebacate, diisopropyl sebacate, dioctyl sebacate, diisopropyl adipate, dioctyl succinate; octyldodecyl myristate, hexyldecyl myristate, octyldodecyl isostearate, Octyldodecyl palmitate cetyl octanoate, hexyldecyl octanoate, isotridecyl isononanoate, isononyl isononanoate, octyl isononanoate, isotridecyl isononanoate, isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate, octyldodecyl neodecanoate, oleyl oleate, olein Higher alcohol fatty acid esters such as octyldodecyl acid, octyldodecyl ricinoleate, octyldodecyl lanolin fatty acid, hexyldecyl dimethyloctanoate, octyldodecyl erucate, hydrogenated castor oil isostearate; cetyl lactate, diisostearyl malate, monoisostearic acid Hydrogenated castor oil and other oxyacid esters; glyceryl trioctanoate, glyceryl trioleate, glyceryl triisostearate, caprylic/capric triglyceryl, tri(caprylic/capric/myristic/stearic) glyceryl , hydrogenated rosin glyceryl (hydrogenated ester gum), neopentyl glycol dioctoate, 2-butyl-2-ethyl-1,3-propanediol dioctoate, propylene glycol dioleate, pentaerythrityl tetraoctanoate, hydrogenated rosin Polyhydric alcohol fatty acid esters such as pentaerythrityl, (hydroxystearic acid/stearic acid/rosin acid) dipentaerythrityl, diisopropyl dimer dilinoleate, diisostearyl dimer dilinoleate, di(isostearyl/phytosteryl dimer dilinoleate ), dimer dilinoleic acid (phytosteryl/behenyl), dimer dilinoleic acid (phytosteryl/isostearyl/cetyl/stearyl/behenyl), dimer dilinoleyl dimer dilinoleate, dimer dilinoleyl diisostearate, dimer dilinoleyl water Derivatives of dimer acid or dimer diol such as added rosin condensate, dimer dilinoleic acid hydrogenated castor oil, hydroxyalkyl dimer dilinoleyl ether; coconut oil fatty acid monoethanolamide, coconut oil fatty acid diethanolamide, lauric acid monoethanolamide, laurin Fatty acid alkanolamides such as acid diethanolamide, palmitic acid monoethanolamide, palmitic acid diethanolamide; low viscosity dimethylpolysiloxane, high viscosity dimethylpolysiloxane, cyclic dimethylsiloxane (decamethylcyclopenta siloxane), methylphenylpolysiloxane, diphenylpolysiloxane, silicone resin, silicone rubber, amino-modified polysiloxane such as aminopropyl dimethicone and amodimethicone, cation-modified polysiloxane, polyether-modified polysiloxane, polyglycerin-modified polysiloxane, sugar-modified silicones such as polysiloxane, alkyl-modified polysiloxane, fatty acid-modified polysiloxane, and fluorine-modified polysiloxane; fluorine-based oils such as perfluorodecane, perfluorooctane, and perfluoropolyether;
More preferably, the oily component is one or more selected from the group consisting of hydrocarbon oils and ester oils.

Moisturizing agents include polyhydric alcohols such as propylene glycol, glycerin, diglycerin, polyglycerin, DPG, 1,2-alkanediol, 1,3-butanediol, 3-methyl-1,3-butanediol, and hyaluron. sodium acid, citrate, urea, lactic acid bacteria culture, yeast extract, eggshell membrane protein, bovine submandibular gland mucin, hypotaurine, sesame lignan glycoside, betaine, chondroitin sulfate, glutathione, polyethylene glycol, sorbitol, carbitol, lactic acid sodium, sodium 2-pyrrolidone-5-carboxylate, albumin, trimethylglycine; collagen, gelatin, elastin, collagen-degrading peptide, elastin-degrading peptide, keratin-degrading peptide, conchiolin-degrading peptide, silk proteolytic peptide, soybean proteolytic peptide, wheat Protein peptides such as proteolytic peptides, casein-degrading peptides, acylated peptides, and derivatives thereof; amino acids such as arginine, serine, glycine, threonine, glutamic acid, cysteine, methionine, leucine, tryptophan; Aloe extract, hamamelis water, loofah water, chamomile extract, licorice extract, comfrey extract and other animal and plant extracts, natural ceramide (type 1, 2, 3, 4, 5, 6), hydroxyceramide, pseudoceramide and ceramides such as glycosphingolipids.

Polymers, thickeners, and gelling agents include guar gum, locust bean gum, queens seed, carrageenan, galactan, gum arabic, tara gum, tamarind, farcereran, karaya gum, tororo mallow, cara gum, tragacanth gum, pectin, alginic acid and its salts. , mannan, starch, xanthan gum, dextran, succinoglucan, curdlan, hyaluronic acid and its salts, xanthan gum, pullulan, gellan gum, chitin, chitosan, agar, chondroitin sulfate, casein, gelatin, albumin, methylcellulose, ethylcellulose, hydroxyethylcellulose , hydroxypropylcellulose, carboxymethylcellulose and its salts, methylhydroxypropylcellulose, cationized cellulose, soluble starch, carboxymethylstarch, methylstarch, propylene glycol alginate, polyvinyl alcohol, polyvinylpyrrolidone, polyoxyethylene-polyoxypropylene copolymer Combined, partially saponified polyvinyl acetate, maleic acid copolymer, polyacrylic acid ester copolymer, carboxyvinyl polymer, polyacrylic acid and its salts, acrylic acid/methacrylic acid ester copolymer, amphoteric methacrylic acid ester copolymer Polymer, acrylic acid/alkyl methacrylate copolymer, diallyldimethylammonium chloride/acrylamide copolymer, acrylic acid/diallyldimethylammonium chloride/acrylamide copolymer, acrylic acid/cationized methacrylic acid ester copolymer, Acrylic acid/cationized methacrylic acid amide copolymer, chloride methacrylic acid choline ester polymer, cationized guar gum, nitrocellulose; 12-hydroxystearic acid and its salts, dextrin fatty acid ester, silicic anhydride, metal soap, organically modified Clay minerals, sucrose fatty acid esters, fructo-oligosaccharide fatty acid esters and the like can be exemplified.

Examples of antioxidants include BHT, BHA, propyl gallate, vitamin E (tocopherol) and/or derivatives thereof, vitamin C (ascorbic acid) and/or derivatives thereof, sulfites, hydrogen sulfites, and the like. . Examples of preservatives include phenols, phenoxyethanol, hydroxybenzoic acid and its salts, 1,2-pentanediol, 1,2-hexanediol, halogenated bisphenols, acid amides, quaternary ammonium salts, and the like. can. Examples of bactericidal agents include trichlorocarbanide, zinc pyrithione, benzalkonium chloride, benzethonium chloride, chlorhexidine, halocarban, hinokitiol, phenol, isopropylphenol, and photosensitizers. Examples of chelating agents include edetate, phytic acid, phosphonic acids, sodium oxalate, polyamino acids and the like. pH adjusters, acids, and alkalis include citric acid, lactic acid, glycolic acid, succinic acid, acetic acid, hydrochloric acid, monoethanolamine, diethanolamine, triethanolamine, isopropanolamine, arginine, sodium hydroxide, potassium hydroxide, and aqueous ammonia. , guanidine carbonate and the like.

Examples of solvents include lower alcohols such as ethanol and 2-propanol; acetone, ethyl acetate, ethylene glycol monoethyl ether, toluene and the like.

Examples of exfoliating/dissolving agents include salicylic acid, sulfur, resorcinol, selenium sulfide, pyridoxine, and the like. Examples of antipruritic agents include diphenhydramine hydrochloride, chlorpheniramine maleate, camphor and the like. Examples of antiphlogistic agents include glycyrrhizic acid and derivatives thereof, guaiazulene, hydrocortisone acetate, prednisone, and the like. Examples of antiperspirants include aluminum chlorohydroxy, aluminum chloride, zinc oxide, and zinc paraphenolsulfonate. Examples of cooling agents include menthol and methyl salicylate. Examples of antihistamines include diphedramine hydrochloride, chlorpheniramine maleate, glycyrrhetinic acid derivatives and the like. Examples of astringents include citric acid, tartaric acid, lactic acid, aluminum/potassium sulfate, and tannic acid. Examples of stimulants include cantharis tincture, ginger tincture, capsicum tincture, benzyl nicotinate and the like. Hair growth agents and blood circulation promoters include plant extracts and tinctures such as assembly extract, capsicum tincture, ginger tincture, cantharis tincture; cepharanthine, vitamin E and its derivatives, γ-oryzanol, nicotinic acid and nicotinic acid benzyl ester. etc., allantoin, photosensitive element 301, photosensitive element 401, pentadecanoic acid monoglyceride, flavanonol derivatives, minoxidil and the like.

Examples of reducing agents include thioglycolic acid, cysteine, cysteamine, and the like. Examples of the oxidizing agent include aqueous hydrogen peroxide, ammonium persulfate, sodium bromate, and the like.

Examples of α-hydroxy acids and derivatives thereof include lactic acid, glycolic acid, fruit acid, hydroxycapric acid, long-chain α-hydroxy fatty acid, long-chain α-hydroxy fatty acid cholesteryl, and the like.

Vitamins and derivatives thereof include vitamins such as vitamin A, vitamin B group, vitamin D, vitamin E, pantothenic acid, biotin; ascorbyl stearate, ascorbyl palmitate, ascorbyl dipalmitate, magnesium ascorbyl phosphate, ascorbic Examples include vitamin derivatives such as sodium phosphate, tocopherol nicotinate, tocopherol acetate, tocopherol linoleate, and tocopherol ferulate.

Examples of sugars and derivatives thereof include cyclodextrin, β-glucan, chitin, chitosan, glucose, trehalose, pectin, arabinogalactan, dextrin, dextran, glucosylethyl methacrylate polymer or copolymer, and the like. . Examples of organic acids include acetic acid, propionic acid, citric acid, abietic acid, and tartaric acid.

Examples of enzymes include lysozyme chloride, papain, pancreatin, protease, and the like. Examples of nucleic acids include disodium adenosine triphosphate and the like. Examples of hormones include estradiol, estrone, ethinyl estradiol, cortisone, hydrocortisone, prednisone and the like.

The present invention will be specifically described below with reference to Examples, but the present invention is not limited by these.

[Synthesis]
<Synthesis Example 1>
136.7 g (0.121 mol) of polyglycerin having a hydroxyl value of 840, 350.3 g (1.030 mol) of behenic acid and 35.2 g (0.103 mol) of eicosanedioic acid were placed in a reaction vessel, and 0.25 g of of sodium hydroxide was added, and the mixture was reacted at 250° C. for 3 hours under a nitrogen stream to obtain 500 g of a reaction product having an esterification rate of 55%.

<Synthesis Example 2>
157.6 g (0.140 mol) of polyglycerol having a hydroxyl value of 840, 323.1 g (0.950 mol) of behenic acid and 40.63 g (0.119 mol) of eicosanedioic acid were placed in a reaction vessel, and 0.25 g of of sodium hydroxide was added, and the mixture was reacted at 250° C. for 3 hours under a nitrogen stream to obtain 500 g of a reaction product having an esterification rate of 55%.

<Synthesis Example 3>
131.9 g (0.174 mol) of polyglycerol having a hydroxyl value of 890, 355.0 g (1.044 mol) of behenic acid and 35.7 g (0.104 mol) of eicosanedioic acid were placed in a reaction vessel, and 0.25 g of of sodium hydroxide was added, and the mixture was reacted at 250° C. for 3 hours under a nitrogen stream to obtain 500 g of a reaction product having an esterification rate of 55%.

<Synthesis Example 4>
123.4 g (0.267 mol) of polyglycerol having a hydroxyl value of 970, 363.2 g (1.068 mol) of behenic acid and 36.5 g (0.107 mol) of eicosanedioic acid were placed in a reactor, and 0.25 g of of sodium hydroxide was added, and the mixture was reacted at 250° C. for 3 hours under a nitrogen stream to obtain 500 g of a reaction product having an esterification rate of 55%.

<Synthesis Example 5>
114.4 g (0.364 mol) of polyglycerin having a hydroxyl value of 1070, 3718 g (1.093 mol) of behenic acid and 37.4 g (0.109 mol) of eicosanedioic acid were placed in a reaction vessel, and 0.25 g of water was added. After adding sodium oxide, a reaction was carried out at 250° C. for 3 hours under a nitrogen stream to obtain 500 g of a reaction product having an esterification rate of 55%.

<Synthesis Example 6>
107.0 g (0.446 mol) of polyglycerin having a hydroxyl value of 1150, 379.0 g (1.115 mol) of behenic acid and 38.1 g (0.111 mol) of eicosanedioic acid were placed in a reactor, and 0.25 g of of sodium hydroxide was added, and the mixture was reacted at 250° C. for 3 hours under a nitrogen stream to obtain 500 g of a reaction product having an esterification rate of 55%.

<Synthesis Example 7>
95.3 g (0.574 mol) of polyglycerol having a hydroxyl value of 1400, 390.3 g (1.148 mol) of behenic acid and 39.3 g (0.115 mol) of eicosanedioic acid were placed in a reaction vessel, and 0.25 g of of sodium hydroxide was added, and the mixture was reacted at 250° C. for 3 hours under a nitrogen stream to obtain 500 g of a reaction product having an esterification rate of 55%.

<Synthesis Example 8>
74.1 g (0.805 mol) of glycerin having a hydroxyl value of 1830, 410.7 g (1.208 mol) of behenic acid and 41.3 g (0.121 mol) of eicosanedioic acid were placed in a reaction vessel, and 0.25 g of After adding sodium hydroxide, reaction was carried out at 250° C. for 3 hours under nitrogen stream to obtain 500 g of a reaction product having an esterification rate of 55%.

<Synthesis Example 9>
227.2 g (0.201 mol) of polyglycerol having a hydroxyl value of 840, 232.8 g (0.685 mol) of behenic acid and 58.5 g (0.171 mol) of eicosanedioic acid were placed in a reaction vessel, and 0.25 g of of sodium hydroxide was added, and the mixture was reacted at 250° C. for 3 hours under a nitrogen stream to obtain 500 g of a reaction product having an esterification rate of 25%.

<Synthesis Example 10>
97.5 g (0.201 mol) of polyglycerin having a hydroxyl value of 840, 399.8 g (1.176 mol) of behenic acid and 25.1 g (0.073 mol) of eicosanedioic acid were placed in a reaction vessel, and 0.25 g of of sodium hydroxide was added, the reaction was carried out at 250° C. for 3 hours under a nitrogen stream, but the reaction was not completed and no reaction product was obtained.

<Synthesis Example 11>
144.9 g (0.128 mol) of polyglycerin having a hydroxyl value of 840, 371.2 g (1.092 mol) of behenic acid and 3.7 g (0.011 mol) of eicosanedioic acid were placed in a reaction vessel, and 0.25 g of of sodium hydroxide was added, and the mixture was reacted at 250° C. for 3 hours under a nitrogen stream to obtain 500 g of a reaction product having an esterification rate of 50.5%.

<Synthesis Example 12>
127.7 g (0.113 mol) of polyglycerin having a hydroxyl value of 840, 327.2 g (0.962 mol) of behenic acid and 65.8 g (0.192 mol) of eicosanedioic acid were placed in a reaction vessel, and 0.25 g of After adding sodium hydroxide, the reaction was carried out at 250 ° C. for 3 hours under a nitrogen stream, but the cross-linking reaction proceeded excessively and gelled. I didn't.

[Composition]
A composition was prepared by adding 5% of the esters of Synthesis Examples 1 to 9 and 11 to liquid paraffin, but a uniform composition could not be obtained for the esters of Synthesis Examples 9 and 11. For the ester compositions of Synthesis Examples 1 to 8, the viscoelasticity was measured while gradually increasing the strain stress from 0.01% to 100% at a temperature of 20 ° C., and the vibration strain at the maximum of the loss elastic modulus. The stress was compared. Table 1 shows the results.

[Evaluation of touch]
<Examples 1 to 7, Comparative Example 1>
A sensory test was carried out on the texture using compositions obtained by adding 5% of the esters of Synthesis Examples 1 to 8 to liquid paraffin. Evaluation items were three points, "spreadability", "massage", and "feel of use", and were evaluated on a scale of four.

<Examples 8 to 10, Comparative Examples 2 to 4>
Sensory tests on feel were carried out using compositions containing 5% of the ester of Synthesis Example 1 or 8 in ethylhexyl palmitate, isopropyl myristate or tri(caprylic/capric)glyceryl. Evaluation items were three points, "spreadability", "massage", and "feel of use", and were evaluated on a scale of four.

[Nabi]
Sensory evaluation was carried out by 20 panelists. 1 g of the above composition was applied to the forearm, and spreadability was calculated on a scale of 5 out of 5 and the spreadability was calculated and evaluated according to the following criteria. These results are shown in Tables 2 and 3.
(standard)
◎: 4.0 points or more (very good)
○: 3.0 points or more and less than 4.0 points (good)
△: 2.0 points or more and less than 3.0 points (slightly bad)
×: 2.0 points or less (bad)

[Massage]
Sensory evaluation was carried out by 20 panelists. 1 g of the above composition was applied to the forearm, and the massaging properties when the composition was spread with the index finger were calculated on a scale of 5 out of 5, and the average score was calculated and evaluated according to the following criteria. These results are shown in Tables 2 and 3.
(standard)
◎: 4.0 points or more (very good)
○: 3.0 points or more and less than 4.0 points (good)
△: 2.0 points or more and less than 3.0 points (slightly bad)
×: 2.0 points or less (bad)

[Feeling of use]
Sensory evaluation was carried out by 20 panelists. 1 g of the above composition was applied to the forearm, and the feeling of use when the composition was spread with the index finger was calculated as a perfect score of 5, and the average score was calculated and evaluated according to the following criteria. These results are shown in Tables 2 and 3.
(standard)
◎: 4.0 points or more (very good)
○: 3.0 points or more and less than 4.0 points (good)
△: 2.0 points or more and less than 3.0 points (slightly bad)
×: 2.0 points or less (bad)

The compositions of Examples 1 to 7 using the polyglycerol fatty acid ester of the present invention were excellent in spreadability and massaging properties during application, and were excellent in feeling during use. On the other hand, comparison using the ester of Synthesis Example 8 that does not satisfy any of the conditions that the hydroxyl value of polyglycerin is 1400 or less, the esterification rate is 30 to 70%, the vibrational strain at the maximum point is 1% or more, and the value is 5000 Pa or more. The composition of Example 1 was poor in spreadability and massaging properties upon application, and had a bad feeling in use.

As shown in Examples 8 to 10, the polyglycerol fatty acid ester of the present invention can adjust the texture of not only hydrocarbon oils but also various oily components, and can provide good texture. On the other hand, with the ester of Synthesis Example 8, as shown in Comparative Examples 2 to 4, even when various oily components were used, a good feel could not be obtained.

From the above results, it has become clear that the polyglycerol fatty acid ester of the present invention exhibits excellent effects when blended in cosmetics.

The polyglycerol fatty acid ester of the present invention can be suitably used in the field of cosmetics. In particular, it can be suitably used in oily cosmetics.

In the present invention, the polyglycerol has a hydroxyl value of 800 or more and 1400 or less,
The constituent fatty acid is at least one selected from the group consisting of monocarboxylic acids and derivatives thereof, and at least one selected from the group consisting of polycarboxylic acids and derivatives thereof, and the monocarboxylic acid is a linear and a saturated monocarboxylic acid, the polycarboxylic acid is a saturated dicarboxylic acid,
The esterification rate of all constituent fatty acids with respect to the polyglycerin is 40 to 60 %,
The esterification rate of the polycarboxylic acid and its derivative with respect to the polyglycerol is 2 to 8%,
The polyglycerin fatty acid ester is characterized in that the loss elastic modulus of the composition obtained by adding 5% to liquid paraffin is 1% or more in vibrational strain and 5000 Pa or more in stress at the maximum point.

<Synthesis Example 2>
157.6 g (0.140 mol) of polyglycerol having a hydroxyl value of 840, 323.1 g (0.950 mol) of behenic acid and 40.63 g (0.119 mol) of eicosanedioic acid were placed in a reaction vessel, and 0.25 g of of sodium hydroxide was added, and the mixture was reacted at 250° C. for 3 hours under a nitrogen stream to obtain 500 g of a reaction product having an esterification rate of 45% .

In the present invention, the polyglycerol has a hydroxyl value of 800 or more and 1400 or less,
The constituent fatty acid is at least one selected from the group consisting of monocarboxylic acids and derivatives thereof, and at least one selected from the group consisting of polycarboxylic acids and derivatives thereof, and the monocarboxylic acid is a straight chain and a saturated monocarboxylic acid, the polycarboxylic acid is a saturated dicarboxylic acid,
The esterification rate of all constituent fatty acids with respect to the polyglycerin is 40 to 60%,
The esterification rate of the polycarboxylic acid and its derivative with respect to the polyglycerol is 2 to 8%,
The polyglycerin fatty acid ester is characterized in that the loss elastic modulus of a composition obtained by adding 5% to liquid paraffin is 2.5 % or more in vibrational strain and 9000 Pa or more in stress at the maximum point.

Claims (7)

The hydroxyl value of polyglycerol is 1400 or less,
The constituent fatty acids are at least one selected from the group consisting of monocarboxylic acids and derivatives thereof, and at least one selected from the group consisting of polycarboxylic acids and derivatives thereof,
The esterification rate of all constituent fatty acids with respect to the polyglycerin is 30 to 70%,
The esterification rate of the polycarboxylic acid and its derivative with respect to the polyglycerol is 2 to 8%,
1. A polyglycerol fatty acid ester, characterized in that a composition obtained by adding 5% to liquid paraffin has a loss elastic modulus of 1% or more in vibrational strain and 5000 Pa or more in stress at the maximum point. A polyglycerol fatty acid ester according to claim 1, wherein the monocarboxylic acid is behenic acid. 3. The polyglycerin fatty acid ester according to claim 1, wherein the polycarboxylic acid is eicosanedioic acid. A texture modifier comprising the polyglycerin fatty acid ester according to any one of claims 1 to 3. A cosmetic containing the polyglycerin fatty acid ester according to any one of claims 1 to 3 and an oily component. 6. Cosmetics according to claim 5, wherein the oily component is one or more selected from the group consisting of hydrocarbon oils and ester oils. 7. The cosmetic composition according to claim 5, wherein the amount of the polyglycerin fatty acid ester blended is 0.01 to 20% by mass relative to the total amount of components other than water in the cosmetic composition.

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