CN114599343B - Thickening or curing agents for oil agents - Google Patents

Thickening or curing agents for oil agents Download PDF

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CN114599343B
CN114599343B CN202080076002.2A CN202080076002A CN114599343B CN 114599343 B CN114599343 B CN 114599343B CN 202080076002 A CN202080076002 A CN 202080076002A CN 114599343 B CN114599343 B CN 114599343B
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oil
thickening
fatty acid
agent
acid
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CN114599343A (en
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今尾彩惠
土井干雄
樋口智则
川合丈志
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Taiyo Kagaku KK
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    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system

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Abstract

The present invention provides a thickening or solidifying agent for an oil agent, which is a thickening or solidifying agent for an oil agent and contains a polyglycerin fatty acid ester satisfying the following conditions (A) to (E). (A) The average degree of polymerization of the polyglycerol is 10 or more; (B) comprises at least 1 or more straight-chain saturated fatty acids having 16 to 24 carbon atoms; (C) comprises 1 or more selected from the group consisting of hydroxy fatty acids and polycondensates of hydroxy fatty acids; (D) the esterification rate is more than 70 percent; (E) component (B): the mass ratio of the component (C) is 80: 20-98: 2. the thickening or solidifying agent of the present invention can be used as a raw material for cosmetics, pharmaceuticals, foods and beverages, industrial use, and the like.

Description

Thickening or curing agents for oil agents
Technical Field
The present invention relates to: a thickening or solidifying agent for an oil agent characterized by containing a specific polyglycerin fatty acid ester, an oil agent containing the thickening or solidifying agent, and a cosmetic containing the oil agent.
Background
In the field of cosmetics, a method of adding 12-hydroxystearic acid or dextrin fatty acid ester is known as a technique for thickening a liquid oil agent. However, almost all of them have a melting point higher than 75 ℃ or higher, and are difficult to dissolve in oils. Further, in order to thicken a cosmetic oil agent using these components, a large amount of the components needs to be blended, and the feeling of use is not satisfactory, for example, the components become sticky after application and rinsing.
As another technique, a method of adding a polyglycerin fatty acid ester, which has a low melting point and is easily soluble in an oil agent, is known. In addition, no substantial blending is required in order to thicken the cosmetic oil. It is known that a polyglycerol fatty acid ester having a fixed molar ratio of a linear saturated fatty acid having 2 to 28 carbon atoms to an aliphatic saturated dibasic acid having 12 to 28 carbon atoms is used in this method (for example, see patent document 1). However, the amount of the cosmetic oil agent added to thicken the cosmetic oil agent is not sufficient, and there is a problem in feeling of use such as stickiness after application and rinsing.
As a technique for thickening a cosmetic oil agent at a low addition amount, the following techniques are disclosed: the polymerization degree and esterification degree of polyglycerol are specified by fixing the molar ratio of a linear saturated fatty acid having 16 to 22 carbon atoms to a linear saturated fatty acid having 8 to 14 carbon atoms, a branched fatty acid having 18 to 22 carbon atoms, or an unsaturated fatty acid having 18 to 22 carbon atoms (for example, see patent document 2).
As a technique in which a fatty acid in a polyglycerin fatty acid ester is necessarily a hydroxy fatty acid and the polymerization degree of the polyglycerin is 10 or more, an oily base for cosmetics is known as a substitute for lanolin (see, for example, patent document 3). However, the proportion of esterified hydroxy fatty acids is large, and the fatty acids do not reach the thickening effect of cosmetic oils, and cannot be used as thickening or curing agents for cosmetic oils.
Documents of the prior art
Patent document
Patent document 1: japanese patent No. 2700377;
patent document 2: japanese patent No. 5727749;
patent document 3: japanese patent laid-open No. 2006-45145.
Disclosure of Invention
Problems to be solved by the invention
In the case of thickening cosmetic oils, the viscosity recovers after a certain shear rate is applied, which is the preferred operating situation. The oil agent is preferable because it has good appearance when it is transparent. However, the thickened cosmetic oils of patent documents 1 to 3 do not sufficiently satisfy the requirements in terms of viscosity recovery and transparency.
The present invention relates to: provided is a thickening or curing agent which can thicken or cure an oil agent and which is excellent in transparency and viscosity recovery (hereinafter, sometimes referred to simply as "transparency" or "viscosity recovery") of the thickened or cured oil agent. Here, the transparency means the transparency of the oil agent which thickens to 1500-2500 Pa.s at 25 ℃, and the details thereof will be described later. The viscosity recovery property is a property of recovering viscosity after a certain shear rate is applied to an oil agent thickened to 1500-2500 mPas at 25 ℃, and details thereof will be described later.
Means for solving the problems
The present invention relates to the following [1] to [3 ].
[1] A thickening or solidifying agent for an oil agent, which comprises a polyglycerin fatty acid ester satisfying the following conditions (A) to (E):
(A) the average degree of polymerization of the polyglycerol is 10 or more;
(B) comprises at least 1 or more straight-chain saturated fatty acids having 16 to 24 carbon atoms;
(C) comprises 1 or more selected from the group consisting of hydroxy fatty acids and polycondensates of hydroxy fatty acids;
(D) the esterification rate is more than 70 percent;
(E) component (B): the mass ratio of the component (C) is 80: 20-98: 2.
[2] an oil agent comprising the thickening or curing agent of [1 ].
[3] A cosmetic comprising the oil agent according to [2 ].
Effects of the invention
According to the present invention, a thickening or curing agent can be provided which can thicken or cure an oil agent and which is excellent in transparency and viscosity recovery of the thickened or cured oil agent.
Detailed Description
The thickening or solidifying agent of the present invention is a substance that thickens or solidifies an oil agent, and contains a polyglycerin fatty acid ester satisfying the following conditions (a) to (E) (hereinafter, may be referred to as "polyglycerin fatty acid ester according to the present invention"):
(A) the average degree of polymerization of the polyglycerol is 10 or more;
(B) comprises at least 1 or more linear saturated fatty acids having 16 to 24 carbon atoms;
(C) comprises 1 or more selected from the group consisting of hydroxy fatty acids and polycondensates of hydroxy fatty acids;
(D) the esterification rate is more than 70 percent;
(E) component (B): the mass ratio of the component (C) is 80: 20-98: 2.
the polyglycerin constituting the polyglycerin fatty acid ester according to the present invention has an average polymerization degree calculated from a hydroxyl number of 10 or more, preferably 15 or more, more preferably 20 or more from the viewpoint of transparency, and is preferably 50 or less, more preferably 40 or less from the viewpoint of viscosity recovery, and may be in a range of any combination of these ranges. The average polymerization degree of polyglycerol in the present specification means the average polymerization degree of polyglycerol calculated from the hydroxyl value by the terminal group analysis method, and is the average polymerization degree calculated from (formula 1) and (formula 2).
(formula 1) average degree of polymerization = (112.2 × 10) 3 -18 Xhydroxyl value)/(74 Xhydroxyl value-56.1X 10 3 )
(formula 2) hydroxyl value = (a-b). times. 28.05/sample collected amount (g)
a: consumption (ml) of 0.5N Potassium hydroxide solution in blank test
b: consumption (ml) of 0.5N Potassium hydroxide solution in this test
The hydroxyl value in the above (formula 1) was calculated from (formula 2) according to "1996 edition of the Standard oil and fat analysis test method (I) by the Japan oil chemical society", which is the society of Law of Japan oil chemical society.
The polyglycerin fatty acid ester of the present invention comprises (B) at least 1 or more kinds of linear saturated fatty acids having 16 to 24 carbon atoms and (C) 1 or more kinds of constituent fatty acids selected from the group consisting of a hydroxy fatty acid and a condensation product of a hydroxy fatty acid. Here, when the component (C) is contained at a specific ratio or more, the transparency and thickening recovery are excellent, but the thickening effect tends to decrease as the component (C) increases. Therefore, from the viewpoint of transparency and viscosity recovery, the mass ratio of the constituent fatty acids (component (B): component (C)) is 80: 20-98: 2. preferably, the ratio of 85: 15-96: 4. more preferably, the ratio of 90: 10-95: 5.
examples of the linear saturated fatty acid having 16 to 24 carbon atoms include: palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid.
The hydroxy fatty acid is preferably a fatty acid having 9 to 22 carbon atoms as a constituent fatty acid, and specifically, the hydroxy fatty acid includes: hydroxynonanoic acid, hydroxydecanoic acid, hydroxylauric acid, hydroxymyristic acid, hydroxypalmitic acid, hydroxystearic acid, hydroxyarachidic acid, hydroxybehenic acid, ricinoleic acid, hydroxyoctadecenoic acid, and further: castor oil fatty acid or hydrogenated castor oil fatty acid collected from natural oil and fat. Among them, 12-hydroxystearic acid is preferable from the viewpoint of viscosity recovery. As the hydroxy fatty acid polycondensate, there can be exemplified: from the viewpoint of viscosity recovery, 2 to 6-mers of hydroxy fatty acid are preferably 2 to 6-mers of 12-hydroxystearic acid.
The polyglycerin fatty acid ester according to the present invention may contain a fatty acid other than the above-mentioned component (B) and component (C) as its constituent fatty acid, and the total amount of the component (B) and the component (C) in the constituent fatty acid is preferably 95% by mass or more, more preferably 98% by mass or more, and most preferably 100% by mass, from the viewpoint of transparency and viscosity recovery.
The esterification ratio of the polyglycerin fatty acid ester according to the present invention is 70% or more, preferably 75% or more, and more preferably 80% or more from the viewpoint of transparency. The upper limit is not particularly limited, and may be, for example, 100% or less. The higher the esterification ratio, the more excellent the thickening effect, and the excellent transparency because the thickening or curing agent can attain a desired viscosity even with a small addition amount. The esterification ratio in the present specification is a value calculated from the following formula, assuming that the average polymerization degree (n) of polyglycerol calculated from the hydroxyl group value by the terminal group analysis method, the number (n +2) of hydroxyl groups of the polyglycerol, and the number (M) of moles of fatty acid added to the polyglycerol.
Esterification rate (%) = (M/(n +2)) × 100
The polyglycerin fatty acid ester of the present invention can be produced as follows: the above components are added in a composition satisfying the above conditions, and a catalyst such as potassium hydroxide is added to perform an esterification reaction under normal pressure or reduced pressure, thereby obtaining the product.
The content of the polyglycerin fatty acid ester according to the present invention in the thickening or curing agent of the present invention is preferably 50% by mass or more, more preferably 70% by mass or more, further preferably 90% by mass, and most preferably 100% by mass, from the viewpoint of transparency and thickening recovery property. The thickening or curing agent of the present invention may optionally contain the following other components: dextrin fatty acid ester, inulin fatty acid ester, fatty acid glyceride, polyglycerol fatty acid ester, behenic acid ditecanedioic acid glyceride, sorbitan fatty acid ester, sucrose fatty acid ester (sucrose polystearate, etc.), alkyl phosphate, amino acid oil gelling agent (dibutyl lauroyl glutamine, etc.), dibutyl ethylhexanoyl glutamine, metal soap, dialkyl phosphate metal salt, dibenzylidene sorbitol, calcium salt of dehydroabietic acid, microsilica, organically modified clay mineral, hydrocarbon wax (paraffin wax, microcrystalline wax, polyethylene, polypropylene, etc.), hydrogenated oil (behenyl alcohol, hydrogenated castor oil, hydrogenated vegetable oil, hydrogenated palm kernel oil, etc.), wax ester (rice bran wax, candelilla wax, carnauba wax, beeswax, hydrogenated jojoba oil, etc.), higher alcohol (cetyl alcohol, stearyl alcohol, etc.), fatty acid (stearic acid, hydrogenated vegetable oil, hydrogenated palm kernel oil, etc.), wax ester (rice bran wax, candelilla wax, carnauba wax, beeswax, hydrogenated jojoba oil, etc.), higher alcohol (cetyl alcohol, stearyl alcohol, etc.), and the like, Behenic acid, etc.).
The oil agent to be thickened or cured by the thickening or curing agent of the present invention includes: oils such as oils and fats, waxes, hydrocarbon oils, fatty acids, higher alcohols, silicone oils, ester oils, and silicones.
Examples of the fat and oil include: avocado oil, linseed oil, argan oil, sweet almond oil, perilla oil, olive oil, orange sea bream oil (orange roughy oil), cocoa butter, carrot oil, cucumber oil, beef tallow, coconut oil (cocout oil), grape seed oil, sesame oil, wheat germ oil, rice bran oil, camellia oil, safflower oil, shea butter, soybean oil, turtle oil, clove oil, tea oil, evening primrose oil, camellia oil, corn oil, lard, rapeseed oil, coix seed oil, palm kernel oil, peanut oil, castor oil, sunflower oil, hazelnut oil, macadamia nut oil, mink oil, meadowfoam seed oil, cottonseed oil, coconut oil, rose oil, butterfat, coix seed oil, jojoba oil, lavender oil, egg yolk oil, rice oil, lanolin, rosemary oil, and the like; examples of the waxes include: carnauba wax, candelilla wax, spermaceti wax, beeswax, montan wax, rice wax, lanolin wax, and the like; as the hydrocarbon oils, there may be mentioned: isododecane, squalane, ceresin, paraffin, pristane, liquid paraffin, liquid isoparaffin, vaseline, etc.; as the fatty acids, there may be mentioned: arachidonic acid, isostearic acid, undecylenic acid, erucic acid, oleic acid, capric acid, caprylic acid, stearic acid, sebacic acid, palm kernel fatty acid, palmitic acid, hydroxystearic acid, behenic acid, myristic acid, coconut oil fatty acid, lanolin fatty acid, linoleic acid, linolenic acid, etc.; examples of the higher alcohols include: isostearyl alcohol, oleyl alcohol, octyldodecanol, octanol, shark liver alcohol, stearyl alcohol, cetyl alcohol, cetearyl alcohol, decyl alcohol, batyl alcohol, hexyldecyl alcohol, behenyl alcohol, myristyl alcohol, lauryl alcohol, lanolin alcohol, etc.; examples of silicone oils include: dimethylpolysiloxane, diphenyldimethylpolysiloxane, cyclopentasiloxane, trisiloxane, methylphenylpolysiloxane, etc.; as ester oils, there may be mentioned: dioctyl adipate, diisopropyl adipate, diisobutyl adipate, di-2-hexyldecyl adipate, diheptylundecyl adipate, avocado oil fatty acid ethyl ester, alkyl benzoate, glyceryl isostearate, hexyldecyl isostearate, isopropyl isostearate, octyldodecyl isostearate, isocetyl isostearate, isostearyl isostearate, glyceryl isostearate, cholesteryl isostearate, isotridecyl isononanoate, isononyl isononanoate, isodecyl isononanoate, tridecyl isononanoate, octyl isopalmitate, octyl isononanoate, cetyl ethylhexanoate, octyl dodecyl erucate, cetostearyl ethylhexanoate, ethylene glycol fatty acid ester, octyldodecyl erucate, alkyl octanoates (C14, C16, C18) ester, isocetyl octanoate, cetostearyl octanoate, stearyl octanoate, ethyl alcohol fatty acid ester, ethylene glycol fatty acid ester, octyl octanoate dodecyl octanoate, alkyl octanoate (C14, C18) ester, isocetyl octanoate, cetostearyl octanoate, stearyl octanoate, Cetyl octanoate, isostearyl octanoate, ethyl oleate, oleyl oleate, octyldodecyl oleate, decyl oleate, phytosterol oleate, cetyl decanoate, cetyl octanoate, dioctyl succinate, polypropylene glycol oligomer succinate, lanolin acetate, glyceryl diisostearate, neopentyl glycol diisostearate, propylene glycol dioctanoate, neopentyl glycol didecanoate, neopentyl glycol dioctanoate, ethylene glycol dioleate, propylene glycol didecanoate, hexyldecyl dimethyloctanoate, octyldodecyl dimethyloctanoate, propylene glycol dipelargonate, hexyldecyl stearate, dialkyl carbonate, decaglyceryl isostearate, pentaerythritol tetraoctanoate, diglyceryl tetraisostearate, triisoglyceryl tristearate, diglyceryl triisostearate, polyglyceryl triisostearate, Trimethylolpropane triisostearate, glycerol trioleate, glycerol trioctoate, trioctyl amine, trimethylolpropane tricaprylate, glycerol tri (caprylate/caprate), lauryl lactate, octyl dodecyl lactate, hexyl decyl neodecanoate, decyl nonaisostearate, isostearyl palmitate, isopropyl palmitate, octyl palmitate, isocetyl palmitate, octyl hydroxystearate, isotridecyl myristate, isocetyl myristate, isostearyl myristate, isopropyl myristate, octyl dodecyl myristate, isostearyl laurate, isopropyl lanolate, hexyl laurate, octyl dodecyl ricinoleate, tocopheryl linoleate, octyl dodecyl ricinoleate, diisostearyl malate and the like; examples of the silicone include: aminopropyl dimethicone, alkyl methicone, alkoxy-modified silicone, (dimethicone/vinyl dimethicone) crosspolymer, (stearyloxymethicone/dimethicone) copolymer, (dimethicone/methylcetyloxy silicone) copolymer, stearyl dimethicone, cetyl dimethicone (cetyldimethicone silicone), methylhydrogenpolysiloxane, phenyltrimethicone, polyether-modified organopolysiloxane, polyoxyalkylene alkyl methicone/methylpolysiloxane copolymer, and the like. Further, as the oil agent, there can be exemplified: stem, flower bud, leaf, root, pericarp, bark, resin essential oil, etc. from plant. Among them, liquid paraffin, cetyl ethylhexanoate, and olive oil are preferable from the viewpoint of transparency and thickening recovery.
The amount of the thickening or curing agent added in the present invention is preferably 0.01 to 50 parts by mass, more preferably 0.2 to 30 parts by mass, and still more preferably 0.5 to 20 parts by mass, based on 100 parts by mass of the oil agent. An oil agent containing the thickening or solidifying agent of the present invention (hereinafter, may be referred to as "oil agent of the present invention") is useful as a raw material for cosmetics, pharmaceuticals, foods and beverages, industrial use, and the like, and is excellent in transparency and viscosity recovery, and therefore, is suitably used as an oil agent for cosmetics.
Cosmetics containing the oil agent of the present invention can be widely applied to beauty cosmetics, skin cleansers, skin care products, hair cosmetics, and the like. For example, one can cite: foundation makeup, powder foundation, foundation make-up, foundation cream, stick foundation, concealer, loose powder, foundation cake, blush, lipstick, lip gloss, lip pencil, lip balm (lipstick), eyebrow pencil, eyebrow powder, eyebrow pencil, eyebrow line liquid, mascara make-up, eyelash lotion, eye shadow, color nail polish, nail care, nail polish, solid soap, cleansing foam, cleansing powder, cleansing gel, cleansing cream, cleansing oil, spot makeup remover, lotion, emulsion, gel/lotion, oil, cream, massage cream, hand cream, body cream, mask, exfoliating mask, wiping/rinsing mask, exfoliating agent (gommage), eye care cosmetic, lip care cosmetic, body cleansing product, body lotion, body milk, body lotion (body lotion), body emulsion, hand lotion, and the like skin cosmetic; hair cosmetics such as shampoo, hair rinse, hair conditioner, hair styling agent, hair dye, and hair perm liquid.
The raw materials that can be blended in the oil agent of the present invention and the cosmetic containing the oil agent of the present invention are not particularly limited, and the following components can be exemplified in addition to the thickening or solidifying agent of the present invention. For example, as the anionic surfactant, there can be mentioned: fatty acid salts, alkyl ether carboxylates, N-acylamino acid salts, alkane sulfonates, α -olefin sulfonates, α -sulfomethyl ester salts, alkylbenzene sulfonates, alkylsulfosuccinates, acyl isethionates, alkyl sulfate ester salts, alkyl ether sulfate ester salts, alkyl phosphate ester salts, polyoxyethylene alkyl ether phosphate ester salts, and the like; as the cationic surfactant, there can be mentioned: alkylamine salts, fatty acid amide amine salts, monoalkyl type quaternary ammonium salts, dialkyl type quaternary ammonium salts, benzalkonium type quaternary ammonium salts, and the like; as amphoteric surfactants, there may be mentioned: alkyl amino acid salts, alkyl dimethyl amino acetic acid betaines, alkyl dimethyl amino sulfobetaines, and the like; examples of the nonionic surfactant include: fatty acid glycerides, sucrose fatty acid esters, sorbitan fatty acid esters, propylene glycol fatty acid esters, polyethylene glycol fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, polyoxyethylene lanolin alcohols, polyoxyethylene sorbitol beeswax, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, polyoxyethylene sterols, polyoxyethylene hydrogenated sterols, polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene alkyl ethers, polyglycerol fatty acid esters, alkyl glycerol ethers, alkyl polyglycosides, alkyl alkanolamides, polyoxyethylene glycerol fatty acid esters, and the like; examples of the emulsifier for food include: glycerin fatty acid ester, organic acid monoglyceride, polyglycerin fatty acid ester, propylene glycol fatty acid ester, polyglycerin condensed ricinoleate, sorbitan fatty acid ester, sucrose fatty acid ester, lecithin, enzymatically degraded lecithin, etc.; examples of the hydrocarbons include: ozokerite, ceresin, paraffin, microcrystalline wax, fischer-tropsch wax, polyethylene wax, and the like; examples of the polyhydric alcohols include: erythritol, xylitol, glycerol, diglycerin, dipropylene glycol, sorbitol, trehalose, 1, 3-butylene glycol, propylene glycol, 1, 2-pentanediol, polyethylene glycol, polyoxyethylene glycerol, polypropylene, polyoxypropylene glycerol ether, polyoxypropylene diglycerin ether, polyoxypropylene butyl ether, polyoxyethylene/polyoxypropylene butyl ether, polyoxyethylene methyl glucoside, polyglycerol, maltitol, mannitol, and the like; examples of the thickening/film-forming agents include: hydroxyethyl acrylate/methoxyethyl acrylate copolymer, acrylic resin alkanolamine solution, acrylamide/styrene copolymer, acrylic acid/acrylamide/ethyl acrylate copolymer, octylamide acrylate/hydroxypropyl acrylate/butylaminoethyl methacrylate copolymer, gum arabic, carboxyvinyl polymer, sodium alginate, propylene glycol alginate, ethyl cellulose, cationized guar gum, carrageenan, karaya gum, sodium carboxymethyl cellulose, agar, xanthan gum, guar gum, quince seed gum, crotonic acid/vinyl acetate/vinyl neodecanoate copolymer, guar hydroxypropyltrimonium chloride, synthetic sodium/magnesium silicate, (vinylpyrrolidone/VA) copolymer, gellan gum, guar gum, crotonic acid/vinyl acetate/vinyl neodecanoate copolymer, guar hydroxypropyltrimonium chloride, synthetic sodium/magnesium silicate, and mixtures thereof, Cyclodextrin, dimethyl distearyl ammonium hectorite, cellulose derivatives, tamarind gum, dextrin fatty acid esters, starches, sodium starch phosphate, tragacanth, hydroxyethyl cellulose, hydroxypropyl methylcellulose, pectin, polyacrylamides, sodium polyacrylate, polyvinyl alcohol, polyvinylpyrrolidone, methyl cellulose, vinyl acetate/vinylpyrrolidone copolymer, vinyl acetate/crotonic acid copolymer, vinyl methyl ether/butyl maleate copolymer, vinylpyrrolidone/styrene copolymer, alkyl acrylate copolymer, polyacrylic acid, sodium polyacrylate, polyalkyl acrylate, methacryloylethyldimethyl betaine/methacryloylethyltrimethylammonium chloride/methoxypolyethylene glycol methacrylate copolymer, locust bean gum, sodium polyacrylate, sodium, potassium, sodium, and sodium, and sodium, and sodium, and sodium, and sodium, and sodium, pentaerythritol abietate and the like; examples of the oil gelling agent include: dextrin fatty acid ester, sucrose fatty acid ester, polyglycerol fatty acid ester, fatty acid glyceride, starch fatty acid ester, 12-hydroxystearic acid, aluminum isostearate, calcium stearate, rice bran wax, carnauba wax, candelilla wax, shellac wax, beeswax, microcrystalline wax, ceresin, paraffin wax, dibutyl lauroyl glutamine, dibutyl ethylhexanoyl glutamine, and the like; as mucopolysaccharides, there may be mentioned: sodium hyaluronan, sodium chondroitin sulfate, sodium hyaluronate, and the like; as the fluorine compound, there may be mentioned: silicone film-forming agents such as trifluoroalkyldimethyltrimethylsiloxysilicate, polyperfluoroethylmethoxy difluoroethyl PEG phosphate, polyperfluoroethylmethoxy difluorohydroxyethyl, trimethylsiloxysilicate, and crosslinked methylpolysiloxane; as the colored inorganic pigment, there can be mentioned: white inorganic pigments such as iron oxide, titanium oxide, zinc oxide, cerium oxide, barium sulfate, etc., carbon black, chromium oxide, chromium hydroxide, dark blue, ultramarine, etc.; examples of the white body powder include: talc, muscovite, phlogopite, lepidolite, biotite, synthetic mica, sericite (serilite), synthetic sericite, kaolin, silicon carbide, bentonite, smectite, alumina, magnesia, zirconia, antimony oxide, diatomaceous earth, silicic anhydride, aluminum silicate, aluminum magnesium metasilicate, calcium silicate, barium silicate, magnesium silicate, calcium carbonate, magnesium carbonate, hydroxyapatite, boron nitride, or the like; examples of the organic polymer resin powder include: copolymer resins such as polyurethane resins, silicone resins, cellulose resins, fluorine resins, polyamide resins, polyethylene resins, polyacrylic resins, polyester resins, polystyrene resins, and styrene-acrylic copolymers, and polypropylene resins; examples of the organic low-molecular-weight powder include: zinc stearate, N-acyl lysine, and the like; examples of the natural organic powder include: starch, silk powder, cellulose powder, etc.; examples of the organic pigment powder include: zirconium, barium or aluminum lakes such as red No. 3, red No. 104, red No. 106, red No. 201, red No. 202, red No. 226, red No. 228, blue No. 404, yellow No. 4, yellow No. 5, yellow No. 401, orange No. 203, orange No. 204, orange No. 205, green No. 3, blue No. 1, etc.; examples of the metal powder include: composite powders such as aluminum powder, gold powder, silver powder, etc., fine-particle titanium oxide-coated mica titanium, fine-particle zinc oxide-coated mica titanium, barium sulfate-coated mica titanium, titanium oxide-containing silica, zinc oxide-containing silica, titanium oxide-coated glass powder, etc.; examples of the glitter powder include: a glitter (lamenagene) of titanium dioxide-coated mica, titanium dioxide-coated bismuth oxychloride, iron oxide mica titanium, cyanosis-treated mica titanium, carmine-treated mica titanium, bismuth oxychloride, fish scale foil, etc., polyethylene terephthalate/aluminum/epoxy resin laminated powder, polyethylene terephthalate/polyolefin laminated film powder, polyethylene terephthalate/polymethyl methacrylate laminated film powder; as lecithin derivatives, there may be mentioned: hydrogenated soybean phospholipids, soybean phospholipids hydroxide and the like; examples of alcohols include: preservatives such as benzoate, photosensitizer, parabens, phenoxyethanol, salicylic acid, sorbic acid and isopropylmethylphenol, whitening agents such as ethanol and isopropyl alcohol, arbutin, ellagic acid, kojic acid and ascorbate derivatives, ultraviolet absorbers, chelating agents such as saccharides, ethers and ketones, edetate, hydroxyethane diphosphonate, polyphosphate and gluconic acid, amino acids, vitamins, pH regulators, glycyrrhizic acid derivatives, plant extracts, perfumes, essential oils and the like.
The present invention will be specifically described below with reference to examples and comparative examples, but the present invention is not limited to these examples.
Examples
Preparation of thickening or curing agent
Example 1
A reaction flask was charged with 78.4g of polyglycerin having an average polymerization degree of 20, 295.9g of behenic acid (C22) and 25.7g of 12-hydroxystearic acid (hydroxy C18), and 0.8g of potassium hydroxide was added thereto, followed by esterification reaction at 250 ℃ to obtain a thickening or curing agent comprising a polyglycerin fatty acid ester having an esterification rate of 84%. (in the case where (1) is a linear saturated fatty acid having 16 to 24 carbon atoms and (2) is a polycondensate of a hydroxy fatty acid and a hydroxy fatty acid, the blending ratio (mass ratio) of (1): 2) is 92: 8.)
Examples 2 to 15 and comparative examples 1 to 7
By carrying out the same operation as in example 1, polyglycerin fatty acid ester-containing thickening or curing agent was obtained by charging polyglycerin fatty acid ester-containing thickening or curing agent into a reaction flask at the blending ratio (mass ratio) shown in tables 1 and 2, adding 0.8g of potassium hydroxide to the polyglycerin fatty acid ester-containing thickening or curing agent, and then carrying out an esterification reaction at 250 ℃. The esterification rates are shown in tables 1 and 2. The "hydroxy C182.5-mer" used in example 8 was prepared by charging 300.0g of 12-hydroxystearic acid into a reaction flask, adding 0.8g of potassium hydroxide, and then conducting a dehydration condensation reaction at 250 ℃ until the acid value was 77.6. The "hydroxy C186-mer" used in example 9 was prepared by charging 300.0g of 12-hydroxystearic acid into a reaction flask, adding 0.8g of potassium hydroxide, and then subjecting the mixture to a dehydration condensation reaction at 250 ℃ until the acid value became 32.8.
Test example 1
1.5g of each thickening or solidifying agent of examples/comparative examples and 48.5g of liquid paraffin (MORESCO WHITE P-70 manufactured by MORESCO Co., Ltd.) were weighed into a 50ml glass bottle (mouth inner diameter ϕ 32X bottle diameter ϕ 45X height 78 mm). These were dissolved by heating at 90 ℃ and allowed to stand at 20 ℃ for 2 hours to prepare a sample to which 5.0 mass% of the thickening or curing agent of each example/comparative example was added. The gel strength of the obtained sample was measured. The gel strength is expressed as the rebound strength (g) at 1mm advancement of the plunger. In the gel strength measurement, FUDOH RHEOMETER RT-2002D-D manufactured by Rheotech, Inc. was used, and a plunger having a cylindrical shape and a diameter of 12.7mm was used. The results of measuring the gel strength in test example 1 are shown in tables 1 and 2.
Figure DEST_PATH_IMAGE002
Figure DEST_PATH_IMAGE004
Test example 2
The liquid paraffin thickened by adding the thickening or curing agent of each example/comparative example (MORESCO WHITE P-70 manufactured by MORESCO Co., Ltd.) was measured for transmittance from absorbance at 650.0nm by a spectrophotometer using a quartz cuvette with an optical path length of 1.0 cm. The transmittance was calculated by taking the absorbance of the liquid paraffin not added as 100% transmittance. The viscosity of the liquid paraffin thickened by adding the thickening or curing agent of each example/comparative example was adjusted to 1500-2500 mPas at 25 ℃ to evaluate the transmittance at that time. The viscosity of the liquid paraffin to which no thickening or curing agent was added was 24mPa · s. The viscosity of the liquid paraffin when the transmittance was measured, the amount of the thickening or curing agent added in each example/comparative example, and the transmittance measured in test example 2 were as shown in table 3. In comparative examples 2 and 6, even when 10% by mass was added, the viscosity was 1500mPa · s or less, and the preparation of the sample was difficult, and therefore the measurement was impossible. The transmittance is preferably at least 17%, more preferably at least 30%, even more preferably at least 40%, and still more preferably at least 50%.
Test example 3
The thickening or solidifying agent and liquid paraffin (MORESCO WHITE P-70, MORESCO Co., Ltd.) of each example/comparative example were heated and dissolved at 80 ℃ and stirred at 40rpm until the liquid temperature became 40 ℃, and then the stirring was stopped and the mixture was cooled to 25 ℃ to prepare a thickened sample. The addition amount was adjusted so that the viscosity of the liquid paraffin thickened with the thickening or curing agent of each example/comparative example was 1500-2500 mPas at 25 ℃. The viscosity of the liquid paraffin to which the thickening or curing agent of each example/comparative example was not added was24 mPas. The prepared liquid paraffin was subjected to a shear rate of 1s using an ARES-G2 dynamic viscoelasticity measuring apparatus (manufactured by TAinstinstruments) -1 15 minutes, 100s -1 1 minute, 1s -1 The viscosity was measured for 15 minutes. At an applied shear rate of 1s -1 The maximum viscosity at 15 minutes was an initial viscosity A (mPas) and the applied shear rate was 100s -1 Then becomes 1s -1 When the viscosity at the time point of 15 minutes is the recovered viscosity B (mPa · s), the viscosity recovery rate (%) = the recovered viscosity B (mPa · s)/the initial viscosity a (mPa · s) × 100 is calculated. The viscosity of the liquid paraffin during the measurement, the amount of the thickening or curing agent added in each example/comparative example, and the viscosity recovery rate measured in test example 3 are shown in table 3. In comparative examples 2 and 6, the viscosity at 10% by mass addition was 1500mPa · s or less, and it was difficult to prepare a sample, and thus it was not possible to measure the viscosity. The viscosity recovery rate is preferably 55% or more. Note that the shear rate is 1s -1 Corresponding to the load applied during the circulation/transportation of the cosmetic, with a shear rate of 100s -1 Corresponding to the load applied by the cosmetic product when it is vibrated and stirred, and filled into the container.
Figure DEST_PATH_IMAGE006
The same procedure as in test example 1 was carried out except that olive oil was used instead of liquid paraffin, and the gel strength in the case of using the thickening or solidifying agents of example 1 and comparative example 1 was measured. The results are shown in Table 1. The same operations as in test examples 2 and 3 were carried out except that olive oil was used instead of liquid paraffin, and the transmittance and the viscosity recovery in the case of using the thickening or curing agents of example 1 and comparative example 1 were measured. The results are shown in Table 4.
Figure DEST_PATH_IMAGE008
Preparation of liquid Paraffin cleaning oil
The following components 1 to 4 were heated and dissolved at 80 ℃, stirred and cooled at a rotation speed of 40rpm until the liquid temperature reached 40 ℃, and then stirred and cooled to 25 ℃ to prepare each liquid paraffin clean oil. The amount of component 1 was adjusted so that the viscosity of the liquid paraffin-based clean oil at 25 ℃ was 1500-. The results are shown in Table 5. The viscosity of the liquid paraffin-containing cleaning oil to which component 1 was not added was 172mPa · s.
(ingredient)
1. Thickening or curing agents (polyglyceryl fatty acid esters) of each example/comparative example;
2. polyglycerol-6-dicaprate (manufactured by Sunsoft Q-102H-C/Suzuku K.K.) (8 parts by mass);
3. polyglycerin-10 diisostearate (manufactured by Sunsoft Q-192Y-C/Sun chemical Co., Ltd.) (12 parts by mass);
4. liquid paraffin (MORESCO WHITE P-70/MORESCO, Inc.) (80 parts by mass).
Figure DEST_PATH_IMAGE010
Preparation of vegetable clean oil
The same operations as for the liquid paraffin-based clean oil were carried out except that the following components 1 to 6 were used, and each vegetable-based clean oil was prepared and the transmittance and the viscosity recovery rate were measured in the same manner as in test examples 2 and 3. The results are shown in Table 6. The vegetable-based clean oil to which component 1 was not added had a viscosity of 64mPa · s.
(ingredient)
1. The thickening or curing agent (polyglyceryl fatty acid ester) of example 1 or comparative example 1;
2. polyglycerol-2 sesquioleate (manufactured by Sunsoft Q-17B-C/Suzu chemical Co., Ltd.) (14 parts by mass);
3. polyglycerol-2 decanoate (manufactured by Sunsoft Q-10D-C/Suzuku K.K.) (6 parts by mass);
4. tri (caprylic/capric) glyceride (Sunoil MCT-7/manufactured by Sundaik chemical Co., Ltd.) (24 parts by mass);
5. olive oil (CROPURE OL/Croda Japan Co., Ltd.) (48 parts by mass);
6. jojoba oil (purified jojoba oil/manufactured by honor corporation) (8 parts by mass).
Figure DEST_PATH_IMAGE012
As is clear from the results in tables 1 to 4, it is understood that the oil solutions thickened or cured by adding the thickening or curing agents of examples 1 to 15 to liquid paraffin or olive oil are excellent in gel strength, transparency and viscosity recovery. On the other hand, the oil agent thickened or solidified by adding the thickening or solidifying agent of comparative examples 1,2, 6, and 7 to liquid paraffin or olive oil had low gel strength, and was not thickened or solidified at a low addition amount, and thus had poor transparency. The oil solutions thickened or solidified by adding the thickening or solidifying agents of comparative examples 3 to 5 to liquid paraffin had poor viscosity recovery properties because the fatty acid combined with the long-chain saturated fatty acid was not a hydroxy fatty acid, although the gel strength was high. Further, as shown in tables 5 and 6, it was found that the cleaning oils using the thickening or curing agents of examples 1 to 15 were excellent in transparency and viscosity recovery even when used in actual cleaning oils.
Formulation example 1 oily cleansing gel
Figure DEST_PATH_IMAGE014
The oily cleansing gel obtained in formulation example 1 had a moderate viscosity, was excellent in recovery properties, and had transparency.
Formulation example 2 oily massage gel
Figure DEST_PATH_IMAGE016
The oily massage gel obtained in formulation example 2 had an appropriate viscosity, was excellent in viscosity recovery, and had transparency.
Formulation example 3 Hair oil essence (hair oil stress, hair care essence oil)
Figure DEST_PATH_IMAGE018
The hair oil essence obtained in formulation example 3 had an appropriate viscosity, excellent viscosity recovery properties, and transparency.
Formulation example 4W/O type skin lotion
Figure DEST_PATH_IMAGE020
The W/O type skin lotion obtained in formulation example 4 had a thick texture, had an appropriate viscosity, and was excellent in stability.
Formulation example 5W/O type skin cream
Figure DEST_PATH_IMAGE022
The W/O type cream obtained in formulation example 5 had a thick feeling in use, had an appropriate viscosity, and was excellent in stability.
Formulation example 6O/W type sunscreen cream
Figure DEST_PATH_IMAGE024
The O/W sunscreen cream obtained in formulation example 6 was excellent in emulsion stability even when it contained powder. Further, the oil-based curable composition has a high film-forming property due to its oil-based curing function, and is excellent in water resistance after being applied to the skin and dried.
Formulation example 7 lip gloss
Figure DEST_PATH_IMAGE026
The lip balm obtained in formulation example 7 had a good feeling in use because of its viscosity recovery property, and also had excellent skin adhesion.
Industrial applicability
The thickening or solidifying agent of the present invention can be used as a raw material for cosmetics, pharmaceuticals, foods and beverages, industrial use, and the like.

Claims (6)

1. A thickening or solidifying agent for an oil agent, which comprises a polyglycerin fatty acid ester satisfying the following conditions (A) to (E):
(A) the average polymerization degree of the polyglycerol is 10-40;
(B) comprises at least 1 or more straight-chain saturated fatty acids having 16 to 24 carbon atoms;
(C) 1 or more selected from 2-6 polymers of hydroxy fatty acid with 9-22 carbon atoms and hydroxy fatty acid with 9-22 carbon atoms;
(D) the esterification rate is more than 70 percent;
(E) component (B): the mass ratio of the component (C) is 80: 20-98: 2.
2. a thickening or curing agent according to claim 1, wherein the oil agent is a fat or oil.
3. The thickening or curing agent according to claim 1, wherein the oil agent is a hydrocarbon oil or an ester oil.
4. The thickening or solidifying agent according to any one of claims 1 to 3, wherein the oil is an oil for cosmetics.
5. An oil agent comprising the thickening or curing agent according to any one of claims 1 to 4.
6. A cosmetic comprising the oil agent according to claim 5.
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