JP2012020984A - Ester derivative and cosmetic containing the ester derivative, external preparation, coating material and ink composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an oily component which provides a high degree of safety, suppresses feeling of oiliness when applied to skin, has light feel and air permeability, is emollient, and originates from vegetables, and to provide a cosmetic, an external preparation, a coating material, and an ink composition containing the oily component.SOLUTION: There is disclosed an ester derivative comprising 2-octanol originating from vegetables: is as chemically stable and polar as an ester derivative comprising 2-ethylhexanol originating from petroleum; provides a high degree of safety; and has unique feel of suppressing feeling of oiliness when applied to skin, having light feel and air permeability, and being emollient. Further, the ester derivative of 2-octanol can be utilized for a cosmetic, an external preparation, a coating material, and an ink composition.

Description

  The present invention relates to a plant-derived ester derivative of 2-octanol and a cosmetic, an external preparation, a paint, and an ink composition containing the ester derivative.

  Conventionally used oily ingredients include fats, waxes, hydrocarbons, synthetic esters, etc., which are widely used in various cosmetics and pharmaceuticals using their unique properties, structures, ingredients, etc. . Its purpose is to protect the skin as an over-fat agent, form a hydrophobic film on the skin surface, suppress moisture transpiration, provide skin flexibility, lubricity, friction effect on the skin surface, etc. Can be mentioned. These purposes only use the natural properties of the oil to cover the skin surface and protect the skin.

  In addition, emollients used for the purpose of suppressing excessive water volatilization on the skin surface are oily substances. By forming a thin film on the skin surface, the frictional resistance is reduced, and the skin surface is smoothed. It suppresses excessive water transpiration from the epithelial cells into the atmosphere and strengthens the hydration of the stratum corneum. Among substances currently used as raw materials for cosmetics and external preparations, substances said to be emollients include fatty oil esters, lanolin and its derivatives, higher alcohols, hydrocarbons, fatty acids, sterins, as well as natural oils and fats. (Non-Patent Document 1).

  Most cosmetics and external preparations, except for some, are applied on the skin surface for several hours or more, so they must not interfere with the physiological function of the skin. In particular, a substance that completely covers and seals the skin surface causes the stratum corneum to swell, impairing the physiological function of the skin and causing some damage.

  On the other hand, plant-derived materials are attracting attention as sustainable biomass materials with little environmental impact, and switching from petroleum-derived materials, which are limited resources, is progressing in many fields.

  As an oily phase component with emollient properties that have oil functionality, high safety, suppress oily feeling when applied to the skin, have a light and smooth feel and breathability, and retain moisture with a tight feel Although an ester of 2-ethylhexanol having a branched chain is used (Patent Document 1), 2-ethylhexanol is a petroleum-derived raw material, and a product using a plant-derived raw material is demanded.

  In addition, although ester of 2-ethylhexanol has high dispersibility of powder and solubilizing ability of oil phase components, it is also used as an oil phase component of paints and inks (Patent Document 2). Attempts have been made to use plant-derived solvents with a low environmental impact. Ink containing a plant-derived fatty acid ester component as a solvent has a low environmental impact, and there is no ink bleeding or ink penetration through thin paper, and a high-density printed matter with excellent image reproducibility has been obtained (Patent Literature) 3). However, there is no report on the ester of plant-derived 2-octanol.

Japanese Translation of National Publication No. 09-506359 JP 2005-105273 A JP-A-2005-132907

“New Cosmetics Handbook”, Nikko Chemicals Co., Ltd., Nippon Surfactant Co., Ltd., Toshi Pigment Co., Ltd., Cosmos Technical Center Co., Ltd., Nicoderm Co., Ltd. 2006, p. 1-86

  The present invention provides oil with a function, is highly safe, suppresses oily feeling when applied to the skin, has a light and light feel, and is breathable, and has an emollient property that retains moisture with a tight feel. It is to provide a plant-derived oily component and a cosmetic, an external preparation, a paint and an ink composition containing the oily component.

  As a result of intensive studies in view of the above circumstances, the present inventors have found that 2-octanol can be used as a plant-derived secondary alcohol. And the ester derivative which has 2-octanol which is a plant-derived raw material as a constituent component is chemically stable and polar as much as the petroleum-derived ester derivative of 2-ethylhexanol, and is highly safe for the human body, In addition, when applied to the skin, the oily feeling is suppressed, it is airy with a smooth and light feel, and it has a unique feel with emollient that retains moisture with a soft feel. The present inventors have found that ester derivatives of octanol can be used in cosmetics, external preparations, paints and ink compositions.

（式中、Ｒは、直鎖又は分岐のアルキル基あるいはアルケニル基を有する脂肪酸、炭素数２以上の多価カルボン酸、ヒドロキシ酸からなる群から選択されるカルボン酸残基、Ｒ１は、一般式（２）で表される２−オクタノール残基を示す。）

That is, the present invention
[1] An ester derivative of 2-octanol represented by the general formula (1).

Wherein R is a fatty acid having a linear or branched alkyl group or alkenyl group, a carboxylic acid residue selected from the group consisting of a polycarboxylic acid having 2 or more carbon atoms and a hydroxy acid, and R1 is a general formula (The 2-octanol residue represented by (2) is shown.)

  The 2-octanol is preferably derived from a plant.

Furthermore,
[2] A cosmetic, external preparation, paint or ink composition comprising an ester derivative of 2-octanol represented by the general formula (1).

  The ester derivative of 2-octanol represented by the general formula (1) of the present invention is a chemically stable and polar oily component, which is highly safe to human body, soluble, compatible, miscible Excellent dispersibility of pigments and inorganic substances, and suppresses oily feeling when applied to the skin, has a light and smooth feel and breathability, and has a unique emollient feel that retains moisture with a soft feel ing. Therefore, the ester derivative of 2-octanol represented by the general formula (1) of the present invention is used as an oil component of cosmetics and external preparations, and as an oil component to be blended in oil-type or emulsion-type pharmaceuticals. Even if it shows an excellent effect.

  Further, since the ester derivative of 2-octanol represented by the general formula (1) of the present invention has high powder dispersibility and solubilization ability of oil phase components, pigments such as paints and inks, and powder dispersion Even if it is used as an emulsifier for an agent or an aqueous dye, it exhibits an excellent effect.

  Plant-derived 2-octanol, which is a constituent of the ester derivative of 2-octanol represented by the general formula (1) of the present invention, can generally be derived from castor oil, but ricinoleic acid is a constituent. As long as it has a plant component, it is not limited to castor oil.

  The ester derivative of 2-octanol represented by the general formula (1) of the present invention is generally a fatty acid having a linear or branched alkyl group or alkenyl group, a polyvalent carboxylic acid having 2 or more carbon atoms, or a hydroxy acid. It is obtained by an esterification reaction with the plant-derived 2-octanol represented by the formula (1), and is appropriately purified as necessary.

  Although it does not specifically limit as said fatty acid, The fatty acid which has a C1-C30 linear alkyl group or alkenyl group is mentioned. For example, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, behenic acid, undecylenic acid, Examples include oleic acid, linoleic acid, linolenic acid, arachidonic acid, docosahexaenoic acid, and eicosapentaenoic acid.

  The branched fatty acid is not particularly limited, and examples thereof include fatty acids having a branched alkyl group or alkenyl group having 3 to 30 carbon atoms. Examples include isopropionic acid, isobutyric acid, isovaleric acid, isooctylic acid, isostearic acid, neoheptanoic acid, neodecanoic acid, neotridecanoic acid and the like.

  Although it does not specifically limit as C2-C2 or more polyhydric carboxylic acid, A C2-C30 linear polyhydric carboxylic acid is mentioned. For example, oxalic acid, malonic acid, succinic acid, adipic acid, azelaic acid, sebacic acid and the like can be mentioned.

  Moreover, it does not specifically limit as a hydroxy acid etc., However, The fatty acid which has a C2-C30 hydroxyl group is mentioned. For example, citric acid, glycolic acid, tartaric acid, lactic acid, 12-hydroxystearic acid, ricinoleic acid and the like can be mentioned.

  When a polyvalent carboxylic acid is used, the 2-octanol ester derivative represented by the general formula (1) of the present invention may be a polyester such as a diester derivative or a triester derivative. The polyvalent ester may exhibit the effect of the present invention more.

  Moreover, when using polyhydric carboxylic acid, it combines with 1 type (s) or 2 or more types of other alcohol components according to the utilization purpose with 2-octanol represented by General formula (2) utilized by this invention. The ester derivative of 2-octanol represented by (1) can also be synthesized.

The 2-octanol represented by the general formula (2) and other alcohol components according to the purpose of use are not particularly limited, but heptanol, octanol, decanol, undecanol, lauryl alcohol, myristyl alcohol, pal Methyl alcohol, stearyl alcohol and the like can be mentioned, and these may be used alone or in combination of two or more.

  When a hydroxy acid is used, the ester derivative of 2-octanol represented by the general formula (1) of the present invention may be an oligoester, and the oligoester may exhibit the effect of the present invention more. is there.

  Among these fatty acids, branched fatty acids, polyvalent carboxylic acids having 2 or more carbon atoms, and hydroxy acids, preferred components are lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, 12-hydroxystearic acid, sebacin Acid, tartaric acid, lactic acid and the like. If these are used, the effect of this invention can be exhibited more.

  When used as an oil, use of a linear or branched fatty acid or the like makes it possible to obtain an oil having a less oily feeling and a lighter feel and breathability. When used as a dispersant or solubilizer, the use of a branched fatty acid, hydroxy acid, polyvalent carboxylic acid, etc. improves the dispersibility and solubilization ability, and can exhibit more excellent effects.

  Although it does not specifically limit as a manufacturing method of the ester derivative of 2-octanol represented by General formula (1) of this invention, It obtains by the dehydration condensation reaction of 2-octanol and carboxylic acids in presence of a catalyst. be able to. Moreover, it can obtain also by transesterification with fats and oils.

  In general, oils and fats and waxes have high viscosity, light specific gravity, stickiness during use, and poor spread. Most hydrocarbons are extracted from petroleum resources, except for special ones obtained from natural animal and vegetable oils or waxes. These mineral raw materials have problems in that they are too oily compared to animal and plant raw materials and do not have very good dermatological properties. Synthetic ester oils are sometimes problematic in terms of safety, and there are problems in terms of touch and acidity.

  Since the ester derivative of 2-octanol represented by the general formula (1) of the present invention is made of a raw material collected from plant resources, it is highly safe for the human body and suppresses an oily feeling when applied to the skin. It has a smooth and light feel and breathability, and has a unique feel with emollient that retains moisture with a tight feel.

  The ester derivative of 2-octanol represented by the general formula (1) of the present invention is used as an oily component in cosmetics and external preparations, as an oily component to be blended in oil-type or emulsion-type pharmaceuticals, etc. It can be used as pigments such as inks and inks, powder dispersants and aqueous dye emulsifiers.

  The blending amount of the ester derivative of 2-octanol represented by the general formula (1) of the present invention in the cosmetic or skin external preparation of the present invention varies depending on the use and form of the skin external preparation, but usually 0.1 to 99. It is mass%, Preferably it is 0.2-50 mass%, More preferably, it is 0.5-20 mass%. If it is this range, the effect of this invention can be exhibited more.

  In addition to the ester derivative of 2-octanol represented by the general formula (1), the cosmetic or external preparation of the present invention includes various components that are usually used in cosmetics according to the purpose of use, such as drugs and extracts. Active ingredients, vitamins, ultraviolet absorbers, powders, antioxidants, preservatives, antibacterial agents, pigments, fragrances, and the like may be mixed and added. Alcohols, fatty acids, oils and fats, waxes, surfactants, humectants, other water-soluble polymers and resins may be mixed and added for the purpose of homogeneous stability and viscosity adjustment.

  Uses of the cosmetics and external preparations of the present invention are not particularly limited. For example, lotions, creams, emulsions, serums, foundations, lipsticks, eyeliners, mascaras, cleansing foams, cleansing creams, cleansing gels, etc. It can be suitably used in the fields of toiletries such as cosmetics, shampoos and rinses, pharmaceuticals such as sunscreens or sun creams, lip balms, urea creams and ointments.

  The plant-derived 2-octanol ester derivative specified in the present invention can be used for a part or all of the oil phase component of cosmetics and external preparations containing an oil phase component. The content of the oil phase component in the cosmetic and the external preparation can be used at a predetermined content depending on the type of the cosmetic and the external preparation.

  The content of the 2-octanol ester derivative represented by the general formula (1) of the present invention in the paint or ink composition varies depending on the composition and type of the 2-octanol ester derivative represented by the general formula (1). However, it is preferable to add 1-40 mass% with respect to the total amount of a coating material or ink.

  In addition to the ester derivative of 2-octanol represented by the general formula (1), the paint or ink composition of the present invention includes carbon black, phthalocyanine blue, phthalocyanine green, iron yellow, red rose, zinc oxide, titanium oxide, and disazo. A dispersant such as yellow, carmine 6B, lake red C, and the like, and a dispersant and oil other than the ester derivative of 2-octanol represented by the general formula (1) of the present invention may be added and kneaded as necessary. .

  The present invention will be described more specifically with reference to the following examples, but the present invention is not limited thereto. A compounding quantity is the mass%.

(Production Example 1)
Synthesis of methyl heptyl palmitate 100 g of 2-octanol and 60 g of palmitic acid were charged into a reaction flask and subjected to dehydration condensation at 180 to 250 ° C. in the presence or absence of a catalyst, followed by distillation purification to obtain 130 g of methyl heptyl palmitate. .

Cleansing cream (A)
10% methyl heptyl laurate (product of the present invention)
Polyoxyethylene (10) sorbitan monostearate 2%
Polyoxyethylene (40) sorbitan tetraoleate 1%
Glyceryl stearate 2%
Stearic acid 4%
Cetanol 2%
Cetyl palmitate 2%
Paraffin (135 ° F) 2%
30% mineral oil (# 70)
10% glyceryl tri-2-ethylhexanoate
(B)
1,3-butylene glycol 5%
Arginine 0.1%
Purified water balance (preparation method)
The phase (A) was sufficiently stirred, and the phase (B) previously mixed was added to the phase (A) with stirring. The emulsion composition was prepared by cooling with stirring.

(result)
The obtained cleansing cream was stable, well-familiar to the skin, had a light touch, and was a characteristic cleansing cream whose viscosity suddenly decreased when applied.

Latex (A)
Methyl heptyl palmitate (product of the present invention) 3%
Polyoxyethylene (5) glyceryl monostearate 1%
1% glyceryl stearate
Polyether-modified silicone 0.4%
Potassium stearate 0.4%
Behenyl alcohol 0.4%
Petrolatum 4%
Squalane 10%
Tetra 2-ethylhexyl pentaerythrityl 3%
Jojoba seed oil 1%
(B)
Glycerin 5%
Dipropylene glycol 4%
Maltitol (75% aqueous solution) 1%
Carbomer 0.1%
Sodium hexametaphosphate 0.1%
Purified water balance (C)
Arginine 0.1%
Purified water 10%
(Preparation method)
(A) The phase is heated and dissolved and mixed. The heated and mixed phase (B) was added to phase (A) with stirring. Cooling with stirring, the phase (C) was added and stirred to prepare an emulsified composition.

(result)
The emulsion was very stable, stretched and refreshed.

Cream (A)
Decaglyceryl pentastearate 1%
Stearic acid 3.5%
Cetostearyl alcohol 2.5%
Methyl heptyl myristate (product of the present invention) 1%
Methyl heptyl stearate (product of the present invention) 2%
Hexamethyltetracosane 8%
Macadamia nut oil 8%
Methyl polysiloxane 0.2%
(B)
1,3-butylene glycol 3.0%
Glycerol 3.0%
L-Arginine 0.2%
Purified water balance

(result)
The cream was very stable, stretched and refreshed.

Lipstick (A)
Methyl heptyl palmitate (product of the present invention) 5%
Methyl heptyl palmitate (product of the present invention) 3%
1% methyl heptyl lactate (product of the present invention)
Trimethylheptyl citrate (product of the present invention) 1%
Candelilla wax 10%
Ceresin 5%
Carnauba wax 3%
Microcrystalline wax 3%
Liquid lanolin 15%
Hardened castor oil 3%
Hydrogenated polydecene 10%
(B)
8% pigment
Pearl 10%
Castor oil 23%
(Preparation method)
The (A) phase was dissolved and mixed, and the (B) phase that had been mixed well in advance was kneaded into the (A) phase and then molded to obtain a lipstick.

(result)
The lipstick prepared by the above formulation was a lipstick with high bending strength, little sweating, good elongation and good glue.

Liquid Foundation (A)
Methyl heptyl palmitate (product of the present invention) 3%
Methyl heptyl 12-hydroxystearate (product of the present invention) 1%
Dimethylheptyl sebacate (product of the present invention) 1%
Glyceryl stearate 2.2%
Polyoxyethylene (25) stearic acid 0.8%
Stearic acid 1%
Cetanol 0.5%
Cetyl palmitate 3%
Liquid paraffin 5%
Methyl polysiloxane 0.5%
Propylparaben appropriate amount (B)
Methylparaben appropriate amount Pigment 12%
Purified water balance (preparation method)
The (A) phase and (B) phase were heated to 80 ° C. to dissolve, and the (B) phase was added to the (A) phase and stirred to emulsify, and then cooled with stirring to obtain an emulsified composition.

(result)
The liquid foundation prepared according to the above formulation was a liquid foundation with good dispersibility of the pigment and a light feel.

Sunscreen agent (A)
Methylheptyl isostearate (product of the present invention) 2%
Methyl heptyl oleate (product of the present invention) 0.5%
Methyl heptyl tartrate (present product) 0.5%
Glyceryl stearate 3%
Tetraoleic acid polyoxyethylene (60) sorbit 3%
Cetanol 5%
Stearic acid 2%
4% olive oil
Polyoxymethylphenylsilylene 0.3%
Octyl paradimethylaminobenzoate 2%
Titanium oxide 3%
Butylparaben appropriate amount (B)
Methyl paraben appropriate amount propylene glycol 5%
Purified water balance (preparation method)
The (A) phase and (B) phase were dissolved by heating to 80 ° C., and the (B) phase was added to the (A) phase and stirred, and then cooled with stirring to obtain the above preparation.

(result)
The sunscreen agent prepared by the above formulation was a sunscreen agent with good dispersibility of the powder and a light touch.

Hair conditioner (A)
Stearyltrimethylammonium chloride (50% aqueous solution) 5%
Stearic acid dimethylaminopropylamide 1%
1% glyceryl monostearate
Cetanol 2%
Methyl heptyl isostearate (product of the present invention) 3%
(Castor oil / succinic acid / isostearic acid) condensate 2%
Methyl polysiloxane (100CS) 3%
Cationized cellulose 0.1%
(B)
Glycerin 3%
Purified water balance

(result)
The hair conditioner prepared with the above formulation had a good feel when applied to hair, and was excellent in emollient after use.

Nail enamel (A)
Nitrocellulose 14%
Alkyd resin 16%
Dibutyl phthalate 5%
Dimethylheptyl succinate (Invention product) 1%
Acetyltrimethylheptyl citrate (product of the present invention) 1%
(B)
Ethyl acetate 20%
N-Butyl acetate 35.6%
Ethanol 8.0
(C)
Stearyldimethylbenzylammonium chloride-treated hectorite
0.2
Pigment 0.2
(Preparation method)
The phase (A) and the phase (C) were added to the phase (B), and the mixture was stirred and mixed.

(result)
The nail enamel prepared by the above formulation had good pigment dispersibility and excellent emollient properties.

Ink composition Methyl heptyl caprylate (product of the present invention) 82%
Polyester dispersant 6%
Carbon black 12%
(Preparation method)
Each component was mixed uniformly.

(result)
The ink prepared according to the above formulation was an ink having good miscibility and pigment dispersibility and no bleeding.

Paint methylheptyl laurate (product of the present invention) 1%
(12-hydroxystearic acid / stearic acid / sebacic acid)
Methylheptyl (Invention product) 1%
60% white titanium
Dehydrated castor oil-modified alkyd resin varnish 33%
Liquid paraffin 5%
Manganese dryer 0.5%
(Preparation method)
Each component was mixed uniformly.

(result)
The paint prepared by the above formulation was a paint having good stability, excellent miscibility and pigment dispersibility.

Claims (4)

An ester derivative of 2-octanol represented by the general formula (1).

Wherein R is a fatty acid having a linear or branched alkyl group or alkenyl group, a carboxylic acid residue selected from the group consisting of a polycarboxylic acid having 2 or more carbon atoms and a hydroxy acid, and R1 is a general formula (The 2-octanol residue represented by (2) is shown.)

  The ester derivative according to claim 1, wherein the 2-octanol is derived from a plant.   A cosmetic or external preparation comprising the ester derivative according to claim 1 or 2.   A paint or ink composition comprising the ester derivative according to claim 1 or 2.