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Gelling agent for oil

a gelling agent and oil technology, applied in the direction of disinfection, make-up, candy, etc., can solve the problems of low solubility of oils, formation of heterogeneous gel compositions, and sometimes insufficient gel strength of gel compositions obtained

Inactive Publication Date: 2007-10-11
AJINOMOTO CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a gelling agent for an oil that has superior gel forming ability. The gelling agent is a particular class of acidic amino acid derivatives that can be mixed with an oil to create a gel composition with superior gel strength and transparency. The resulting gel composition has satisfactory strength for applications as cosmetics and is easily applicable to the skin. The invention also provides a method for gel formation from an oil and a use of the gelling agent for preparing a gel composition. Overall, the invention provides a superior gelling agent for oils that can be used in various applications.

Problems solved by technology

However, these gelling agents have a problem of low solubility in oils.
For example, gel compositions prepared by using these gelling agents have a problem of poor stability in a dissolved state, which results in formation of heterogeneous gel compositions or so-called “sweating phenomenon” as exudation of the gelled oils form the surfaces of the gels due to degradation with time.
However, gel compositions obtained sometimes fail to have sufficient gel strength.
As a result, when gel compositions are prepared as cosmetics for dermal application, the compositions may sometimes become tender and have a problem from a viewpoint of strength.
However, the aforementioned gel sticks are also insufficient in strength, and the sticks may sometimes have difficulty in application to the skin.
Moreover, appearance of each gel composition obtained by using the gelling agent and an oil is white and lacks transparency, which is not desired from an esthetic viewpoint.

Method used

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  • Gelling agent for oil
  • Gelling agent for oil

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of N-2-(R,S)-ethylhexanoyl-L-glutamic acid dibutylamide

[0035] 110 g of sodium glutamate monohydrate was dissolved in 140 g of water and 78 g of 27% aqueous sodium hydroxide and the solution was cooled to 10° C. The solution was added with 110 g of acetone and added dropwise with 87 g of 2-ethylhexanoyl chloride and 78 g of 27% aqueous sodium hydroxide. The reaction mixture for the acylation was diluted with 100 g of water and neutralized with 63 g of 95% sulfuric acid to separate an oil. The aqueous layer was removed, and the oil layer was concentrated under reduced pressure to obtain an oily substance. The resulting oily substance was dissolved in 742 g of methanol, and the solution was added with 6.2 g of 95% sulfuric acid and refluxed for 9 hours. The reaction mixture was left stand for cooling to 35° C. and neutralized with 8.8 g of n-butylamine, and then the methanol was evaporated to obtain an oily substance. The resulting oily substance was added with 643 g of to...

example 2

Preparation of N-octanoyl-L-glutamic acid dibutylamide

[0040] 110 g of sodium glutamate monohydrate was dissolved in 140 g of water and 78 g of 27% aqueous sodium hydroxide and cooled to 10° C. The solution was added with 110 g of acetone and added dropwise with 87 g of octanoyl chloride and 90 g of 27% aqueous sodium hydroxide. The reaction mixture for the acylation was diluted with 100 g of water and neutralized with 64 g of 95% sulfuric acid to separate an oil, The aqueous layer was removed, and the oil layer was concentrated under reduced pressure to obtain an oily substance. The resulting oily substance was dissolved in 742 g of methanol, and the solution was added with 6.2 g of 95% sulfuric acid and refluxed for 9 hours. The reaction mixture was left stand for cooling to 35° C. and neutralized with 10.5 g of n-butylamine, and then the methanol was evaporated to obtain an oily substance. The resulting oily substance was added with 630 g of toluene and 191 g of n-butylamine and ...

example 3

Preparation method of N-decanoyl-L-glutamic acid dibutylamide

[0045] In a manner similar to that of the aforementioned Example 1, N-decanoyl-L-glutamic acid dibutylamide was prepared.

[0046] (a) 13C-NMR peaks: 14.10, 14.47, 20.44, 20.48, 23.04, 26.07, 29.65, 29.67, 29.73, 29.83, 29.88, 31.92, 31.97, 32.24, 37.08, 39.70, 39.88, 52.90, 171.60, 173.33, 174.17 (ppm)

[0047] (b) 1H-NMR peaks (CDCl3) δ: 3.250 (m, 4H), 4.360 (m, 1H), 6.190 (brs, 1H), 6.980 (brs, 1H), 7.030 (brs, 1H)

[0048] (c) Wave number of infrared absorption spectrum: 3294.8, 2959.0, 2927.5, 1637.9, 1556.0, 1466.6 (cm−1)

[0049] (d) MS: 410.5 (M−H)−

[0050] Ethyloylglutamic acid dibutylamide, hexanoylglutamic acid dibutylamide, myristoylglutamic acid dibutylamide and palmitoylglutamic acid dibutylamide used in the following comparative examples were produced in a similar manner.

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Abstract

A compound represented by the following general formula (I), wherein R1 and R2 represent a hydrocarbon group having 1 to 26 carbon atoms, preferably a linear or branched alkyl group, R3 represents a hydrocarbon group having 7 to 10 carbon atoms, preferably a linear or branched alkyl group, n represents 1 or 2 provided that the acidic amino acid residue in the molecule is L-aspartic acid residue when n is 1 and said acidic amino acid residue is L-glutamic acid residue when n is 2, and a gelling agent for an oil comprising said compound.

Description

BACKGROUND OF THE INVENTION [0001] 1. Field of the Invention [0002] The present invention relates to a gelling agent for an oil. More specifically, the present invention relates to a gelling agent for an oil which contains a particular class of an amino acid derivative. The gelling agent of the present invention is useful for gelling an oil in a state of a liquid at an ordinary temperature to obtain variety forms of the oil. [0003] 2. Related Art [0004] As gelling agents for an oil that is insoluble in water, for example, polyamide resins, 12-hydroxystearic acid, condensates of an aromatic aldehyde and a polyhydric alcohol whose typical example includes dibenzylidene-D-sorbitol and the like have been known so far. However, these gelling agents have a problem of low solubility in oils. For example, gel compositions prepared by using these gelling agents have a problem of poor stability in a dissolved state, which results in formation of heterogeneous gel compositions or so-called “sw...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K8/89A61K8/04A61K8/28A61K8/365A61K8/44A61K8/92A61Q1/06A61Q15/00A61Q19/00C07C237/22C11C5/00
CPCA61K8/0229C11C5/002A61K8/28A61K8/365A61K8/42A61K8/442A61K8/585A61K8/922A61K2800/262A61K2800/31A61Q1/06A61Q15/00A61Q19/00A61Q19/001C07C237/22A61K8/042
Inventor YAMATO, NAOYAYOSHIHARA, HIDEKI
Owner AJINOMOTO CO INC
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