JPH11323308A - Gelling agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a gelling agent, excellent in solubility to oily materials such as org. solvents and fluorooils and in gelling capacity with them, using a specific ester compd. contg. fluorine. SOLUTION: This gelling agent comprises an ester compd. contg. fluorine represented by formula I, wherein Rf is a fluoroalkyl group, i.e., a 1-20C linear or branched alkyl group at least one of its hydrogen is substituted by fluorine atoms, R<1> is a 9-35C linear or branched alkyl group, and n shows a 1-8 number. Pref., Rf is a 4-20C fluoroalkyl group, R<1> is an 11-35C alkyl group, and n is a 1-6 number, and especially pref., Rf is an 8-20C fluoroalkyl group, R<1> is a 15-35C alkyl group, and n is a 1-4 number. The ester compd. contg. fluorine of the formula I is obtd. by reacting a hydroxy compd. contg. fluorine of the formula: Rf-(CH2 )n-OH (wherein Rf and n are the same with formula I), and a carboxylic acid of formula II (wherein R<1> is the same with formula I), or its halogenated compd., etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a gelling agent for an oil or an organic solvent comprising a fluorine-containing ester compound.

[0002]

2. Description of the Related Art
Organic compounds containing fluorine atoms are known as oils such as cosmetics, detergents, and lubricants because of the functions of fluorine, such as water and oil repellency, low water absorption, and electrical insulation. . In addition, searches for uses other than such uses of organic compounds containing a fluorine atom are also being conducted, for example, as an organic solvent used in cosmetics and the like, as a gelling agent for oils such as ester oils, silicone oils, and fluorine oils. There is a need for useful fluorine-containing compounds.

On the other hand, gluconamide-6-benzoate has recently been reported as a gelling agent for solvents [J. Ch.
em. Soc., Chem. Commun., 545 (1997)]. It can gel a wide range of solvents from polar solvents such as methanol, ethanol and acetonitrile to non-polar solvents. However, it does not dissolve in fluorine oil and cannot be gelled. Gelation ability of solvents has also been reported for vitamin H derivatives [Synthetic Commun., 27 , 2203 (19
97)] Fluorine oil does not dissolve and gelation is impossible.

[0004] Accordingly, an object of the present invention is to provide a fluorine-containing compound which is excellent in solubility in organic solvents and oils such as fluorine oil, and is useful as a gelling agent which is excellent in gelling ability. .

[0005]

According to the present invention, there is provided a compound represented by the general formula (1):
A gelling agent comprising a fluorine-containing ester compound represented by the formula:

[0006]

Embedded image

(Wherein Rf is a straight-chain or branched-chain C 1 -C 1)
At least one hydrogen atom of the alkyl group of 20 represents a fluoroalkyl group substituted with a fluorine atom, R ¹ represents a linear or branched alkyl group having 9 to 35 carbon atoms, and n represents 1 to
Indicates the number 8. )

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION In the fluorine-containing ester compound represented by the general formula (1) of the present invention, Rf is a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms in which at least one hydrogen atom is a fluorine atom. And a fluoroalkyl group having 4 to 20 carbon atoms is preferable, and a fluoroalkyl group having 8 to 20 carbon atoms is particularly preferable. If the carbon number of Rf exceeds 20, the melting point is too high, which is not preferred. R ¹ represents a linear or branched alkyl group having 9 to 35 carbon atoms, preferably an alkyl group having 11 to 35 carbon atoms, and particularly preferably an alkyl group having 15 to 35 carbon atoms. If the carbon number of R ¹ is less than 9, the gelling ability is inferior. N is 1 to 8
The number is preferably 1 to 6, more preferably 1 to 4, especially 2
Is preferred. The fluorine-containing ester compound of the present invention is preferably a compound (solid) having a total melting point of 20 or more, more preferably 24 or more, in order to exhibit gelling ability.

The fluorinated ester compound represented by the general formula (1) of the present invention is represented by the general formula (2): Rf- (CH ₂ ) _n -OH (2) (wherein Rf and n are as defined above) And a fluorine-containing hydroxy compound represented by the general formula (3):

[0010]

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(Wherein, R ¹ has the meaning described above), or a halide (acid chloride) thereof,
It can be produced by reacting a lower alkyl ester, an acid anhydride and the like.

As the fluorine-containing hydroxy compound represented by the general formula (2), a fluoroalkyl group in which at least one hydrogen atom of a linear or branched alkyl group having 1 to 20 carbon atoms is substituted with a fluorine atom is mentioned. Straight-chain alcohols having 1 to 8 carbon atoms, and specific examples of these include
2,2,3,3,3-pentafluoropropanol, 2
-(Perfluorohexyl) ethanol, 2- (perfluorooctyl) ethanol, 2- (perfluorodecyl) ethanol, 6- (perfluoroethyl) hexanol, 6- (perfluorobutyl) hexanol, 6-
(Perfluorohexyl) hexanol, 6- (perfluorooctyl) hexanol, 2,2,3,4,4
4-hexafluorobutanol, 2,2,3,3-tetrafluoropropanol, 1H, 1H, 5H-octafluoropentanol, 1H, 1H, 7H-dodecafluoroheptanol, 1H, 1H, 9H-hexadecafluorononona Linear fluorinated alcohols such as phenol, 2- (perfluoro-3-methylbutyl) ethanol, 2- (perfluoro-5-methylhexyl) ethanol, 2-
(Perfluoro-7-methyloctyl) ethanol, 2
-(Perfluoro-9-methyldodecyl) ethanol,
6- (perfluoro-1-methylethyl) hexanol, 2- (perfluoro-3-methylbutyl) hexanol, 6- (perfluoro-5-methylhexyl) hexanol, 6- (perfluoro-7-methyloctyl)
Examples include branched chain fluorinated alcohols such as hexanol, but are not necessarily limited thereto. Among these fluorine-containing hydroxyl compounds, 2-
Those having a total carbon number of 10 or more such as (perfluorooctyl) ethanol and 2- (perfluorodecyl) ethanol,
It is preferable because it has a high melting point and excellent compatibility with fluorine oil.

The carboxylic acid represented by the general formula (3) includes a carboxylic acid having 10 to 36 carbon atoms, preferably a carboxylic acid having 12 to 36 carbon atoms, and more preferably a carboxylic acid having 16 to 36 carbon atoms. In particular, stearic acid is more preferred.

The fluorine-containing ester compound of the present invention has good compatibility with fluorine oil and the like, and is excellent in gelling ability. Also,
The fluorine-containing ester compound of the present invention is excellent in the gelling ability of an organic solvent such as ethanol used in cosmetics or an oil such as an ester oil or a silicone oil, particularly the gelling ability of a fluorine oil used in a foundation or the like. Therefore, the fluorine-containing ester compound of the present invention is particularly useful as a gelling agent.

[0015]

EXAMPLES Synthesis Example 1 Synthesis of 2- (perfluorodecyl) ethyl stearate

[0016]

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In a 0.5 L four-necked flask equipped with a stirrer, 56.4 g (0.1 mol) of 2- (perfluorodecyl) ethanol, 100 g of anhydrous chloroform, and 7.3 g of triethylamine
(0.1 mol), and the mixture was stirred under a nitrogen atmosphere. While maintaining this solution at 25 to 30 ° C, 30.3 g (0.1 mol) of stearoyl chloride was added dropwise over 30 minutes. The mixture was further stirred for 5 hours, and the formed white precipitate was separated by filtration and concentrated under reduced pressure. The obtained solid was dissolved in hexane and purified by a silica gel column,
The mixture was concentrated again under reduced pressure to obtain 70.6 g (yield: 85%) of 2- (perfluorodecyl) ethyl stearate as a white solid.

Synthesis Examples 2 to 5 and Comparative Synthesis Examples 1 to 3 Fluorinated ester compounds shown in Table 1 were obtained in the same manner as in Example 1 except that the compounds shown in Table 1 were used as the fluorinated hydroxy compound and acid chloride. Was.

[0019]

[Table 1]

Examples 1 to 5 and Comparative Examples 1 to 3 For the fluorine-containing ester compounds obtained in Synthesis Examples 1 to 5 and Comparative Synthesis Examples 1 to 3, the gelling ability of various organic solvents and oils shown in Table 2 was determined. The following method evaluated. Table 2 shows the results.

<Evaluation Method of Gelling Ability> Various fluorine-containing ester compounds were dissolved by heating in a solvent or an oil at a concentration of 10% by weight, and then left at room temperature for 1 hour to visually observe the solution state.

[0022]

[Table 2]

Note) * 1 Ester oil: trade name Estemol N-01, manufactured by Nisshin Oil Co., Ltd. * 2 Silicone oil: trade name SH200C-6CS, manufactured by Toray Dow Corning Silicone Co., Ltd. * 3 Fluorine oil: Product name Fomblin HC-04, manufactured by Ausimont Co., Ltd.

Claims (3)

[Claims] 1. A gelling agent comprising a fluorine-containing ester compound represented by the general formula (1). Embedded image (In the formula, Rf represents a fluoroalkyl group in which at least one hydrogen atom of a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms is substituted with a fluorine atom, and R ¹ represents a straight-chain or branched-chain carbon atom. Represents an alkyl group of 9 to 35, and n represents a number of 1 to 8.) 2. The gelling agent according to claim 1, wherein Rf is a fluoroalkyl group having 4 to 20 carbon atoms, R ¹ is an alkyl group having 11 to 35 carbon atoms, and n is a number of 1 to 6. 3. The gelling agent according to claim 1, wherein Rf is a fluoroalkyl group having 8 to 20 carbon atoms, R ¹ is an alkyl group having 15 to 35 carbon atoms, and n is a number of 1 to 4.