JPS63122775A - Oil gelatinizing agent - Google Patents

Abstract

PURPOSE:To obtain an oil gelatinizing agent useful as a base for lubricating oil, perfume, cosmetic, gel aroma, etc., capable of forming transparent and stable oil gel, having low toxicity and skin irritation and high safety, consisting of a specific monoalkylphosphoric ester salt. CONSTITUTION:The aimed oil gelatinizing agent consisting of a monoalkylphosphoric ester salt (e.g. disodium mono 2-hexyldecylphosphate, etc.) shown by the formula (R is 8-36C branched chain alkyl or alkenyl; X is alkali metal, alkanolamine, basic amino acid with the proviso that one of two X may be H). An oil-containing system is blended with preferably 0.1-10 pts.wt. of the gelatinizing agent, dissolved under heating and then allowed to cool to give (semi)transparent oil gel.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an oil gluing agent comprising a phosphate ester salt.

[Conventional technology and problems]

Oil dal is widely used in cosmetics, cosmetics, viscosity adjustment, shape-retaining binding, etc.

Conventionally, dalifying agents for gluing oil include metal salts of fatty acids such as calcium, lithium, and aluminum, hydrogenated fatty acids such as mustard oil, 1=2 dehydrated metals of D-sorbitol and benzaldehyde, and N - Derivatives such as amides, esters, and amine salts of amino acids, hydrogenated lecithin, and the like are known. Regarding phosphate ester compounds, aluminum salts and iron salts of mixtures of monoalkyl phosphates and zoalkyl phosphates having linear alkyl groups thicken and gluze liquid oils such as hydrocarbons. , is known to be effective as an additive component of lubricating oil (for example, U.S. Pat. No. 3,494,949).
. However, since these are synthesized by salt exchange after neutralization with IJ (hydroxide), the production is complicated, and because excess base interferes with dull formation, carboxylic acid anhydride is added to improve stability. There were some shortcomings that needed to be improved.

Furthermore, most of the oils that are subject to gluing are colorless and transparent, but because the gluing agent creates a higher-order structure in the oil and causes a certain molecular arrangement, the resulting oil glue may be cloudy. However, there are very few that can convert oil into transparent or translucent oils, and the problem is that the types of oils that can be used are limited.

Therefore, in the field of cosmetics and cosmetics, transparent or translucent dal is desired from the viewpoint of product form and usage, so oils that have excellent stability and transparency and can be converted into gels are limited. And, depending on the case, water or water and alcohol? There has been a desire for an oil dal forming agent that is stable and forms transparent or translucent dal even when a third component such as lyol is present.

[Means to solve the problem]

Therefore, as a result of various studies to overcome the above-mentioned drawbacks, the present inventors found that a monoalkyl phosphate ester salt having a branched-chain alkyl group, which can be easily produced, has little skin irritation, and is highly safe, has been found. The present invention was completed based on the discovery that an oil gel that is transparent or semi-transparent and stable in terms of strength can be produced depending on the type of oil to be treated.

That is, the present invention relates to the following general formula (I) RO-P-OX (r)OX (wherein, R is a branched alkyl or alkenyl group having 8 to 36 carbon atoms, and X is an alkali metal, an alkanolamine, or The present invention provides an oil sludge forming agent consisting of a monoalkyl phosphoric acid ester salt represented by the following formula (representing a basic amino acid; however, one of the two X may be a hydrogen atom).

The branched alkyl group or alkenyl group of the monoalkyl phosphate ester salt of the present invention represented by formula (I) includes:
Examples include those branched from the α-position of an alkyl or alkenyl group, those branched from the β-position, and those branched from the β-position, such as 2-ethylhexyl, 2- Ethylhexadecyl, 2-butyltetradecyl, 2-hexyldecyl, 2-butylhexadecyl, 2-octyldodecyl, 2-decyltetradecyl, 2-tetradecyloctadecyl, 2-ethyloctadecyl, 2-dodecylhexadecyl, 2 -hexadecyl eicosyl group etc. are preferable, among which carbon number 10
-28, such as 2-hexyldecyl, 2-octyldodecyl, 2-decyltetradecyl groups, etc. are particularly preferred. Examples of alkali metals include sodium, potassium, lithium, etc. Among them, sodium and potassium are preferred.

Examples of alkanolamines include triethanolamine, monoethanolamine, alkanolamines having hydroxylalkyl having 2 to 3 carbon atoms, and examples of basic amino acids include lysine, histidine, arginine, etc. Among them, arginine is particularly preferable. These monoalkyl phosphate ester salts are obtained by converting high-purity monoalkyl phosphate esters obtained by known methods (e.g., JP-A-61-17594) into alkalis by known methods (e.g., JP-A-58-180,496). It can be easily obtained by neutralizing 1 equivalent or 2 equivalents with an aqueous solution of metal hydroxide, alkanolamine, or basic amino acid, and then distilling off the solvent.

Examples of oils that can be gelled using the oil gelling agent of the present invention include lubricating oils such as turbine oil, machine oil, motor oil, and gear oil; hydrocarbons such as hexane and heptane; silicone oil; Higher alcohol higher fatty acid esters, higher fatty acids, squalane, castor oil, olive oil,
Examples include all oils that are liquid at room temperature, such as animal and vegetable oils such as soybean oil. Among them, aliphatic straight-chain saturated hydrocarbons or aliphatic branched-chain hydrocarbons, such as normal hexane, normal heptane, normal octane, normal decane, normal dodecane, normal tetratecane, normal hexadecane, normal octadecane, isooctane, isodecane, and indodecane. , mineral oils such as intetradecane, inhexadecane, inoctadecane and iso79 roughin; isostearyl cholesteryl ester,
2-ethylhexane R) IJ celite, octadecyl myristate, IQ lumitin isozorogyl,
Ester oils such as inpropyl myristate, decyl oleate, butyl acetate; or squalane, castor oil,
Animal and vegetable oils such as olive oil, soybean oil, cottonseed oil, and camellia oil are preferred, and these may be used alone or in combination of two or more.

Furthermore, an oil gel containing one or more types of oil, water, water and alcohol, or ? A third component such as lyol may also coexist. Examples of alcohols and polyols include ethanol, glycerin, ethylene glycol, diethylene glycol, triethylene glycol, and
-tinzool, butylene glycol, hezotanzool, zolobile/glycol, sorbitol, and the like.

Gluing of oil using the oil dalifying agent of the present invention is carried out by the following method. That is, 0.05 to 20 parts by weight of the monoalkyl phosphate salt of formula (I) is added to the oil-containing system.
A transparent or translucent oil glue can be obtained by mixing preferably 0.1 to 10 parts by weight, heating until the monoalkyl phosphate salt is dissolved, and leaving it at room temperature. In this case, the above-mentioned aliphatic straight-chain saturated hydrocarbons or aliphatic branched-chain hydrocarbons, such as eva-normal hexane, normal heptane, normal octane, normal decane, normal dodecane, normal tetradecane, normal hexadecane, normal octadecane, in-octane, isodecane,
isododecane, isotetradecane, isohexadecane,
Preferably, mineral oils such as inoctadecane and iso79 roughin are present. 0.01-2 for systems containing oil
It may contain 0 parts by weight, preferably 0.01 to 5 parts by weight of water. Furthermore, in addition to oil, water and alcohol? When a third component such as lyol is present, the monoalkyl phosphate salt is 0.05 to 5 parts by weight, preferably 0.5 to 2 parts by weight, and the water is 0.5 to 50 parts by weight, preferably is 2 to 30 parts by weight, alcohol or ? It is preferable to mix and stir 10 to 50 parts by weight, preferably 8 to 40 parts by weight, of Riolu at room temperature until the mixture becomes homogeneous, and then add 25 to 95 parts by weight of oil for dalification.

[Effect]

The mechanism by which phosphate ester salts with branched-chain alkyl or alkenyl groups form transparent or translucent oil glues regardless of the type of oil is not necessarily clear, but branched-chain alkyl or alkenyl groups have special properties in oil. It is thought that transparent or translucent oil slag is formed to create a higher-order structure. Additionally, phosphate ester salts with branched-chain alkyl and alkenyl groups have lower Kraft points and phase transition temperatures than phosphate ester salts with straight-chain alkyl and alkenyl groups, and form transparent or translucent stable oil gels. It is thought that this contributes to the

〔Effect of the invention〕

The oil casing of the present invention can form transparent or translucent and stable oil casings regardless of the target oil, and is highly safe with low toxicity and skin irritation. It can be used in a wide range of applications, not only as a base for industrial products such as agents and crude oil spill prevention agents, but also as a base for cosmetics, cosmetics, and dal fragrances.

〔Example〕

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

Example 1 0.51 of mono-2-hexyldecyl phosphoric acid disodium salt obtained by a known method and 9.52 of iso79 roughin were mixed into 1
Mix and stir in an oil bath at 20°C. Mono 2 at 100℃
-Hexyldecyl phosphate disodium salt dissolves and becomes transparent.

This was left at room temperature to obtain a translucent oil gel.

Example 2 0.5f of mono-2-hexyldecyl phosphate disodium salt obtained by a known method and 0.52% of normal octane were mixed into 1
Mix and stir in an oil bath at 20°C. Mono 2 at 100℃
-Hexyldecyl phosphate disodium salt dissolves and becomes transparent. This was left at room temperature to obtain a translucent oil gel.

Example 3 Zopotassium mono-2-hexyldecyl phosphate obtained by a known method 1. Of and Isono Q rough-in 9. Of12
Mix and stir in an oil bath at 0°C. Mono 2- at 100℃
Zopotassium hexyldecyl phosphate dissolves and becomes transparent. This was left at room temperature to obtain a translucent oil gel.

Example 4 0.5 t of mono-2-hexyldecyl phosphate mono-L-arginine salt obtained by a known method and 9.5 t of n-octane
Mix and stir 2 in an oil bath at 120°C. At 80°C, mono-2-hexyldecyl phosphate mono-L-arginine salt dissolves and becomes transparent. This was left at room temperature to obtain a transparent oil gel.

Example 5 Mono-2-hexyldecyl phosphate mono-L-arginine salt O,St obtained by a known method and n-dodecane 9.5
Mix and stir 1 in an oil bath at 120°C. At 80°C, mono-2-hexyldecyl phosphate mono-L-arginine salt dissolves and becomes transparent. This was left at room temperature to obtain a transparent oil glue.

Example 6 0.5 t of mono-2-hexyldecyl phosphate mono-L-arginine salt obtained by a known method and n-hexadecane 9
．． Mix and stir 52 in an oil bath at 120°C. 80℃
The mono-2-hexyldecyl phosphate mono-L-arginy/salt is dissolved and becomes transparent. This was left at room temperature to obtain a transparent oil glue.

Example 7 0.5 t of mono-2-hexyldecyl phosphate mono-L-arginine salt obtained by a known method and 9.5 t of iso, Q rough in
Mix and stir in a 120°C oil bath. At 80°C, mono-2-hexyldecyl phosphate mono-L-arginine salt dissolves and becomes transparent. Leave this at room temperature to form a transparent oil glue.

Example 8 Mono-2-hexyldecyl phosphate mono-L-arginine salt obtained by a known method i,ot,! : Mix and stir IsonoQ Rough In 9.01 in an oil bath at 120°C. 8
At 0°C, mono-2-hexyldecyl phosphate mono-L-arginine salt dissolves and becomes transparent. Leave this at room temperature to form a transparent oil glue.

Example 9 Mono-2-octyldodecyl phosphate disodium salt obtained by a known method 1. O2 and Isono Q rough-in9. Mix and stir O2 in a 120°C oil bath. Mono 2 at 90℃
- Octyldodecyl phosphate disodium salt dissolves and becomes transparent. This was left at room temperature to obtain a translucent oil dal.

Example 10 Mono-2-decyltetradecyl phosphate disodium salt 1.02 and iso/Q rough-in 9.02 obtained by a known method. O2
Mix and stir in an oil bath at 120°C. At 90°C, mono-2-decyltetrabutyl phosphate disodium salt dissolves and becomes transparent. This was left at room temperature to obtain a translucent oil dal.

Example 11 Mono-2-hexyldecyl phosphate mono-L-arginine salt obtained by a known method 1. Of and iso 79 rough in 9.0
? , water o, o s t are mixed and stirred in an oil bath at 120°C. At 80°C, mono-2-hexyldecyl phosphate mono-L-arginine salt dissolves and becomes transparent. Leave this at room temperature to form a transparent oil glue.

Example 12 Mono-2-hexyldecyl phosphate mono-L-arginine salt obtained by a known method 1. Or and Isono Q rough-in 6, O
f, squalane 3. Mix and stir the Of in an oil bath at 120°C. 2-hexyldecyl phosphate mono-L- at 80°C
Fulginine salt dissolves and becomes transparent. This was left at room temperature to obtain a transparent oil dal.

Example 13 Mono-2-octyldodecyl phosphate disodium salt obtained by a known method 1. Of and Isono Q rough-in 6, Of,
Silicone oil: Mix and stir 3.0 in an oil bath at 120°C. At 90°C, 2-octyldodecyl phosphate disodium salt dissolves and becomes transparent. This was left at room temperature to obtain a translucent oil glue.

Example 14 0.285' of mono-2-hexyldecyl phosphate mono-L-arginine salt obtained by a known method, 0.82 f of water, and 4.32 f of glycerin were stirred at room temperature to make them homogeneous.
2-Ethylhexanoic acid triglyceride 946? were mixed to obtain a transparent oil dal.

Example 15 0.5r of mono-2-hexyldecyl phosphate mono-L-arginine salt obtained by a known method, water λ59. Glycerin 1
0. After stirring Of at room temperature to make it homogeneous, liquid paraffin 87. Of was mixed to obtain a transparent oil dal.

Example 16 0.28 t of mono-2-hexyldecyl phosphate mono-L-arginine salt obtained by a known method.

Water 0.82t, glycerin 10. After stirring Of at room temperature to make it homogeneous, 9 tons of pentaerythritol 2-ethylhexanoate BB was mixed to obtain a translucent oil dal.

Example 17 Mono-2-octyldodecyl phosphate mono-L-fulginine salt obtained by a known method 0.5? Water Z5F, glycerin 8. Or, 1,3-butylene glycol λO? After stirring at room temperature, 2-ethylhexanoic acid triglyceride 87, Of was mixed to obtain a transparent oil dal.

Comparative Example 1 0.5f of mono-hexadecyl phosphate mono-L-arginine salt obtained by a known method and 9.52 f of IsonoQ Roughin were added to 120
Although it was mixed and stirred in an oil bath at ℃, it did not dissolve, completely separated from the oil, and did not produce any glue.

Comparative Example 2 Monohexadecyl phosphate disodium salt O,St obtained by a known method and InnoQ Roughin 9.52 were mixed and stirred in an oil bath at 120°C, but they did not dissolve and were completely separated from the oil, forming a glue. does not generate.

Comparative Example 3 Zopotassium monohexadecyl phosphate O,St obtained by a known method and InnoQ Roughin 9.5f were mixed and stirred in an oil bath at 120°C, but they did not dissolve and were completely separated from the oil, leaving the glue. Not generated.

Comparative Example 4 Monohexadecyl phosphate mono-L- obtained by a known method
Arginine salt 0.28? , water 0.822, glycerin 4
After stirring 32 tons at room temperature to make it homogeneous, 94.69 g of 2-ethylhexanoic acid triglyceride was mixed, but a cloudy oil dal was obtained.

Comparative Example 5 Calcium stearate 0.51 and IsonoQ Roughin were mixed and stirred in an oil bath at 120°C. When the calcium stearate salt was dissolved and left at room temperature, an oil gel was formed, but a transparent gel was not obtained and a cloudy gel was formed.

Test Example 1 The stability test of the oil glues obtained in Examples 7 and 8 was carried out by leaving them in a constant temperature room at 40°C for 20 days. As a result, there was no change in transparency compared to that during gluing. This was confirmed to be a stable oil gel with no fluidity and no oozing of oil.

Test Example 2 The oil dal obtained in Example 17 was heated to -5,10125,40
, 50°C for one month, it was confirmed that the oil glue was stable without separating at any temperature.

Test Example 3 Monostearic acid? Lioxyethylene sorbitan 5? and water 41. After stirring 1.5 t of glycerin and 6 t of 1°3-butylene glycol at room temperature to make them homogeneous, the oil dal obtained by mixing 83.5 t of 2-ethylhexanoic acid triglyceride was prepared in the same manner as in Test Example 2. As a result of examining the stability of the product, oil oozed out at 10°C, and water and oil completely separated at temperatures above 25°C.

Claims (1)

[Claims] 1. The following general formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. are included ▼ (I) (In the formula, R is a branched alkyl or alkenyl group having 8 to 36 carbon atoms, represents an alkali metal, an alkanolamine, or a basic amino acid. However, one of the two X may be a hydrogen atom) An oil gelling agent consisting of a monoalkyl phosphate ester salt represented by: