JP2019116538A - Aluminum soap, method for producing the same and liquid oil composition - Google Patents

Abstract

To provide a metallic soap that makes it possible to obtain a stable viscous product that has high viscosity while maintaining transparency when mixed with a liquid oil that is liquid at room temperature.SOLUTION: An aluminum soap is a C12-22 saturated fatty acid aluminum soap, wherein, a molar ratio of a saturated fatty acid-derived acyl group to aluminum is 1.1 or more and 2.5 or less, and a solubility to hexane at 225°C is 1 g/L or more.SELECTED DRAWING: None

Description

  The present invention relates to a novel saturated fatty acid aluminum soap, which when used in combination with a transparent liquid oil such as hydrocarbon oil, ester oil, silicone oil, etc., has a solidity while maintaining its transparency, and changes in temperature. The present invention relates to obtaining a stable thickener with less change in viscosity.

  Conventionally, thickeners / gelling agents of relatively low polar oils such as hydrocarbon oils and ester oils, emulsifiers of W / O type, metal soaps as stabilizers, particularly aluminum stearate (mono, di, tri salts ) And magnesium stearate are known. Heretofore, in these fatty acid metal soaps, metal salt exchange reaction (metathesis reaction) of an aqueous solution of an alkali salt of an organic acid (organic acid sodium salt, organic acid potassium salt, organic acid ammonium salt) and an aqueous solution of aluminum salt and magnesium salt , And wet reaction).

  For example, Patent Document 1 describes aluminum stearate as a cosmetic for oily eyelashes having sufficient stringing properties and excellent not only long effect but also storage stability.

  In view of the above, Patent Document 2 discloses a cosmetic preparation containing an organic medium which is liquid at normal temperature, wherein aluminum isostearate is blended alone or in combination with another fatty acid metal soap. There is a description.

Moreover, in patent document 3, when manufacturing aluminum 2-ethylhexanoate soap, 10 mass parts of di soaps shown by the formula HO * Al (RCOO) ₂ with the alkali metal salt and aluminum salt of 2-ethylhexanoic acid. The reaction is carried out at a rate such that 1 to 3 parts by mass of trisoap represented by the formula Al (RCOO) ₃ is produced, and the aluminum aluminum 2-ethylhexanoate produced is dried at a temperature not exceeding 50 ° C. Methods have been described for producing aluminum ethylhexanoate soaps.

JP, 2014-129282, A Japanese Patent Application Laid-Open No. 54-64645 Unexamined-Japanese-Patent No. 3-11034

  However, metal soap generally known as a raw material for cosmetics (for example, Patent Document 1) has high gelling ability at a low addition amount, but has low stability against temperature, such as precipitation at room temperature, etc. It was very difficult to obtain highly viscous thickeners and gels.

  The aluminum isostearate of the patent document 2 is obtained by metal salt exchange reaction (metathesis reaction, wet reaction) using aluminum sulfate which is 1 type of aluminum salt used as a raw material, and the thing which can provide transparency is increased. There is a problem that it is difficult to obtain the sticky effect.

  Moreover, since the production method described in Patent Document 3 is also produced by metal salt exchange reaction (metathesis reaction, wet reaction), there is a problem that high thickening effect can not be obtained by the addition of a small amount although transparency can be imparted. There is.

  As described above, a metal soap is desired which is capable of obtaining a stable thickened material having high viscosity while maintaining transparency when mixed with an oil liquid at normal temperature.

  Furthermore, although the viscosity can be increased by increasing the addition amount or combining it with other thickeners, the conventional aluminum soap has a large change in viscosity with temperature change, and it suddenly changes when the temperature becomes low. There is a case where the viscosity is increased and the handling property and the feeling of use are impaired, or when the temperature is high, the viscosity is suddenly reduced to cause a sag. Therefore, a stable thickener having a high thickening effect and a small change in viscosity with respect to temperature change is required.

  An object of the present invention is to provide a metal soap which can obtain a stable thickened material having high viscosity while maintaining transparency when mixed with an oil liquid at normal temperature.

  The inventors of the present invention conducted intensive studies to solve the above problems, and as a result, an aluminum soap comprising saturated fatty acid having 12 to 22 carbon atoms and having solubility in specific hexane is hydrocarbon oil, ester oil, silicone oil, etc. It was found that when used in combination with a liquid oil at room temperature, a thickened material having high solubility and transparency and high stability can be obtained.

That is, the present invention is as follows.
[1] An aluminum soap of a saturated fatty acid having 12 to 22 carbon atoms, wherein the molar ratio of the hydrocarbon acyl group derived from the saturated fatty acid to aluminum is 1.1 or more and 2.5 or less, at 25 ° C. Aluminum soap characterized by having a solubility of 0.5 g / L or more in hexane.

[2] A liquid oil composition comprising the aluminum soap of [1] and a liquid oil.

[3] By using a saturated fatty acid having 12 to 22 carbon atoms and an aluminum trialkoxide having 1 to 6 carbon atoms as raw materials, and reacting 1.4 to 2.7 moles of the saturated fatty acid with 1 mole of the aluminum trialkoxide A method for producing an aluminum soap, characterized by obtaining an aluminum soap.

  According to the aluminum soap of the present invention, by mixing with an oil having a pour point of 25 ° C. or less (hereinafter, referred to as liquid oil), it is possible to obtain a thickened substance with maintained transparency. Moreover, the C12-C22 saturated fatty-acid aluminum soap obtained by the manufacturing method of this invention can obtain the thickener which maintained transparency by mixing with liquid oil. For this reason, the present invention is suitable for cosmetic materials, paint materials and the like for which transparency is required.

Hereinafter, embodiments of the present invention will be sequentially described.
The aluminum soap according to the present invention is an aluminum soap of a saturated fatty acid having 12 to 22 carbon atoms, and the molar ratio of acyl group derived from the saturated fatty acid to aluminum is 1.1 or more and 2.5 or less, and 25 ° C. Has a solubility of 0.5 g / L or more in hexane.

  Such a saturated fatty acid aluminum soap is produced using a saturated fatty acid having 12 to 22 carbon atoms and an aluminum trialkoxide having 1 to 6 carbon atoms as raw materials, and 1.5 to 2.7 moles of the saturated fatty acid are reacted with 1 mole of aluminum trialkoxide It is obtained by

(Saturated fatty acid having 12 to 22 carbon atoms)
When the carbon number of the saturated fatty acid is less than 12, since the effect as a thickener of the saturated fatty acid aluminum soap to be obtained becomes difficult to obtain, the carbon number is 12 or more, and preferably 14 or more. On the other hand, saturated fatty acids having a carbon number of greater than 22 are difficult to obtain industrially, and their reactivity with aluminum trialkoxides is significantly reduced, resulting in low productivity. For this reason, although carbon number of a saturated fatty acid shall be 22 or less, it is still more preferable to set it as 18 or less.

  The saturated fatty acid having 12 to 22 carbon atoms may be either a branched saturated fatty acid or a linear saturated fatty acid, or may contain both.

  As a saturated fatty acid having 12 to 22 carbon atoms, for example, lauric acid, isolauric acid, isotridecanoic acid, myristic acid, isomyristic acid, palmitic acid, isopalmitic acid, stearic acid, isostearic acid, arachic acid, isoarachinic acid, behenic acid And the like, and one or more of these can be used as appropriate selected or combined. Among them, in particular, a branched saturated fatty acid and isostearic acid is particularly preferable, and there is no particular limitation such as a difference in structure.

  By isostearic acid is meant a mixture of one or more branched stearic acids. For example, 5,7,7-trimethyl-2- (1,3,3-trimethylbutyl) -octanoic acid is converted to a branched aldehyde having 9 carbon atoms by oxo reaction of isobutylene dimer, and then by aldol condensation of this aldehyde It can be prepared as a branched unsaturated aldehyde having 18 carbon atoms and then hydrogenated and oxidized (hereinafter abbreviated as "aldol condensation type"), which is commercially available from, for example, Nissan Chemical Industries, Ltd.

  2-Heptylundecanoic acid can be produced by dimerization of nonyl alcohol by Guerbet reaction (also referred to as Guerbet reaction, also called Guerbet reaction) and oxidation, which is commercially available from, for example, Mitsubishi Chemical Corporation. A similar mixture having a slightly different branching position is commercially available from Nissan Chemical Industries, Ltd., and a type in which the starting alcohol is not linear saturated and in which two methyl branches are branched is also commercially available from Nissan Chemical Industries (hereinafter referred to as "Gerbet reaction" Abbreviated as "type"). In addition, methyl branched isostearic acid is obtained, for example, as a by-product of dimer production of oleic acid [see, for example, J. Am. Amer. Oil Chem. Soc. 51, 522 (1974)], for example, those commercially available from Emery Co., Ltd. (hereinafter referred to as "Emery type"). Further starting materials of dimer acid which is a starting material of emery type isostearic acid may include not only oleic acid but also linoleic acid, linolenic acid and the like. There is no particular limitation on the isostearic acid constituting the fatty acid aluminum soap, and any type having different structure as described above can be used, and in particular, emery type isostearic acid is preferable.

<Aluminum trialkoxide>
The aluminum trialkoxide is composed of an alkoxide having 1 to 6 carbon atoms, and the three alkoxides may be the same or different from each other, but the same one is preferably used in terms of availability and the like. 2-5 are preferable and, as for carbon number of an alkoxide, 3-4 are more preferable. Examples of the aluminum trialkoxide include aluminum trimethoxide, aluminum triethoxide, aluminum tri n-propoxide, aluminum triisopropoxide, aluminum tri n-butoxide, aluminum triisobutoxide, aluminum tri sec-butoxide, aluminum tri n-pentoxide, aluminum tri n-hexoxide and the like can be mentioned.

<Amount of preparation>
Aluminum can generally form three bonds, but for reactions with fatty acids due to steric hindrance etc., up to two bonds are the main products. Therefore, 1.4 to 2.7 moles are preferable, as for the preparation amount of the C12-C22 saturated fatty acid per 1 mole of aluminum trialkoxide, 1.5 to 2.5 are more preferable, and 1.5 to 2.3 More preferable

  When the amount of the saturated fatty acid having 12 to 22 carbon atoms is less than 1.4 mol, the ash content increases and the compatibility with liquid oils such as hydrocarbon oil, ester oil, silicone oil decreases, so that precipitation etc. Are more likely to occur. When the amount of fatty acid charged is higher than 2.7 moles, the amount of fatty acid which does not react with the aluminum trialkoxide increases, and the thickening effect decreases.

<Reaction temperature>
The reaction temperature of the aluminum trialkoxide and the saturated fatty acid is 85 to 120 ° C., preferably 90 to 110 ° C. When the reaction temperature is less than 85 ° C., the reaction is delayed. When the reaction temperature is higher than 110 ° C., the polymerization of the saturated fatty acid aluminum soap proceeds to cause precipitation, and the product tends to be colored.

(Molar ratio of hydrocarbon acyl group to aluminum)
The aluminum soap of the present invention has an acyl group derived from a saturated fatty acid. And the molar ratio of this acyl group to aluminum is 1.1 or more and 2.5 or less. If the molar ratio of the acyl group to aluminum is less than 1.1, the compatibility with the liquid oil is reduced and precipitation and the like are likely to occur. preferable. When the molar ratio of the acyl group to aluminum is higher than 2.5, the thickening effect is reduced, so the ratio is set to 2.5 or less, preferably 2.2 or less.

(A value)
In a preferred embodiment, the ash ratio A value (measured ash content / theoretical ash content) of the aluminum soap of the present invention is 0.80 ≦ A ≦ 0.95. The measured ash content is the actual measured value (mass of aluminum oxide) of the sample obtained in the present invention, and the theoretical ash value is a theoretical value obtained from the preparation molar ratio of saturated fatty acid and aluminum alkoxide which are raw materials of aluminum soap. Is the value of If the ash content ratio A value is in the above-mentioned range, the effects of the present invention can be sufficiently obtained, and it is preferable, and 0.82 ≦ A ≦ 0.93 is more preferable.

(solubility)
The solubility in hexane at 25 ° C. of the aluminum soap of the present invention is 0.5 g / L or more, more preferably 1.0 g / L or more. When it is 0.5 g / L and used in combination with a liquid oil such as hydrocarbon oil, ester oil, silicone oil or the like in a high addition amount, a transparent thickened product having high dissolution stability can be obtained. The upper limit of the solubility of the aluminum soap of the present invention in hexane at 25 ° C is not particularly limited, but it is preferably 100 g / L or less from the viewpoint of the high thickening effect.

  The aluminum soap of the present invention preferably has a melt flow rate (MFR) of 5 (g / 10 min) or more and 30 (g / 10 min) or less. Since the aluminum soap in which MFR is in the above range has a certain degree of softness, it is easily dissolved in liquid oil and has a high thickening effect. More preferably, the MFR is 10 (g / 10 min) or more and 30 (g / 10 min) or less. In addition, also about an aluminum soap, MFR is the outflow amount (g / 10 minutes) in 10 minutes of load 21.18N and 190 degreeC measured based on JISK7210.

  The present invention also provides a liquid oil composition comprising the aluminum soap and a liquid oil. The aluminum soap of the present invention can be used as a thickener by optionally changing the type of liquid oil to be dissolved and the addition amount of the aluminum soap according to the respective uses and formulations of cosmetics, paints and the like.

  The liquid oil for dissolving the aluminum soap of the present invention is not particularly limited as long as it is an oil having a pour point of 25 ° C. or less (oil which is liquid at 25 ° C.). Particularly preferred are ester oils that are liquid at 25 ° C., triglycerides that are liquid at 25 ° C., animal and vegetable oils that are liquid at 25 ° C., silicone oils that are liquid at 25 ° C., and fatty acid esters. Of these, fatty acid esters and hydrocarbon oils are particularly preferred.

  In the production method of the present invention, since a saturated fatty acid and a saturated fatty acid ester of an alkoxide are formed simultaneously with the aluminum soap, a mixture of a saturated fatty acid aluminum and a saturated fatty acid ester is obtained. This saturated fatty acid ester is suitable as an aid for rapidly and stably dissolving a saturated fatty acid aluminum soap in a liquid oil having a transparent liquid at normal temperature, particularly hydrocarbon oils, ester oils, silicone oils and other liquid oils. It is.

  As hydrocarbon oils liquid at 25 ° C., liquid paraffin, hydrogenated polyisobutene, hydrogenated polydecene, squalane, squalene, pristane, light isoparaffin, light liquid isoparaffin, heavy liquid isoparaffin, liquid isoparaffin, tetradecene, isohexadecane, isododecane And alpha-olefin oligomers.

  As ester oil liquid at 25 ° C., ethyl oleate, ethyl linoleate, isopropyl myristate, isopropyl palmitate, isopropyl isostearate, cetyl 2-ethylhexanoate, cetyl palmitate, 2-ethylhexyl palmitate, isostearic acid Isostearyl, myristyl myristate, cetyl myristate, isostearyl myristate, isocetyl myristate, hexyl laurate, decyl oleate, octyldodecyl oleate, isononyl isononanoate, 2-ethylhexyl isononanoate, and the like.

  Examples of triglyceride liquid at 25 ° C. include esters of glycerin and caproic acid, caprylic acid, capric acid, 2-ethylhexanoic acid, isotridecanoic acid, isopalmitic acid, isostearic acid, eicosanoic acid and oleic acid.

  Examples of animal and vegetable oils and fats that are liquid at 25 ° C. include olive oil, sunflower oil, safflower oil, castor oil, camellia oil and the like.

  As a silicone oil liquid at 25 ° C., dimethicone, cyclomethicone, phenyl dimethicone and the like can be mentioned.

  The mass ratio of the aluminum soap to the liquid oil (the total mass of the both is 100) is preferably 1:99 to 70:30. By setting the mass ratio of the aluminum soap to 1 or more, the aluminum content in the liquid oil is high, and a sufficient thickening effect can be easily obtained. From this viewpoint, it is more preferable to set the mass ratio of the aluminum soap to the liquid oil to 10 or more and 90 or less. In addition, by setting the mass ratio of aluminum soap to 80 or less, the dissolution stability in liquid oil is improved. From this viewpoint, it is more preferable to set the mass ratio of aluminum to liquid oil to 10 or more and 90 or less.

  Hereinafter, the present invention will be more specifically described by way of examples, but the present invention is not limited by the following examples.

Example 1
500.0 g (1.68 mol) of isostearic acid (Kroda Japan Ltd. Prisorine 3503, acid value 189 mg KOH / g) was added to a heating type kneading kneader attached with a thermometer, and the mixture was heated to 95 ° C. Thereto, 229.3 g (1.12 mol) of aluminum triisopropoxide (reagent grade 1 from Kishida Chemical Co., Ltd.) was added, and the mixture was heated and kneaded. The reaction was stopped when distillation of isopropyl alcohol generated by the reaction ceased to give a viscous solid aluminum isostearate soap.

(Example 2)
500.0 g (1.68 mol) of isostearic acid (Kroda Japan Ltd. Prisorine 3503, acid value 189 mg KOH / g) was added to a heating type kneading kneader attached with a thermometer, and the mixture was heated to 95 ° C. Thereto, 149.6 g (0.73 mol) of aluminum triisopropoxide (reagent grade 1 from Kishida Chemical Co., Ltd.) was added, and the mixture was heated and kneaded. The reaction was stopped when distillation of isopropyl alcohol generated by the reaction ceased to give a viscous solid aluminum isostearate soap.

(Comparative example 1)
300 g of isostearic acid (Croda Japan Ltd. Prisorine 3503, acid value of 189 mg KOH / g) in an 8 L separable flask, and 2500 g of water
Was heated to 60.degree. Subsequently, 84.2 g of 48 mass% sodium hydroxide aqueous solution was added, and it stirred at the same temperature (60 degreeC) for 1 hour, and the isostearic-acid alkali compound salt aqueous solution was obtained. Thereafter, while the temperature was maintained at 60 ° C., 1728.5 g of a 20% by mass aqueous solution of aluminum sulfate was added dropwise over 60 minutes to the aqueous solution of alkali isostearate compound salt. After completion of the dropwise addition, the mixture was kept at 60 ° C., stirred for 10 minutes and aged. 1500 g of water was added to the obtained aluminum isostearate soap aqueous solution slurry and cooled to 40 ° C. or less. Thereafter, the resultant was filtered with a suction filter, washed with water twice with 1000 g of water, and the obtained cake was dried with a tray drier to obtain an isostearic acid fatty acid aluminum soap.

(Comparative example 2)
Isostearic acid (Croda Japan Ltd. Prisorine 3503, acid value 189 mg KOH / g) 300 g in an 8 L separable flask, and 2500 g water
Was heated to 60.degree. Subsequently, 84.2 g of 48 mass% sodium hydroxide aqueous solution was added, and it stirred at the same temperature (60 degreeC) for 1 hour, and the isostearic-acid alkali compound salt aqueous solution was obtained. Thereafter, while the temperature was maintained at 60 ° C., 1296.4 g of a 20% by mass aqueous solution of aluminum sulfate was added dropwise over 60 minutes to the aqueous solution of alkali isostearate compound salt. After completion of the dropwise addition, the mixture was kept at 60 ° C., stirred for 10 minutes and aged. 1500 g of water was added to the obtained aluminum isostearate soap aqueous solution slurry and cooled to 40 ° C. or less. Thereafter, the resultant was filtered with a suction filter, washed with water twice with 1000 g of water, and the obtained cake was dried with a tray drier to obtain an isostearic acid fatty acid aluminum soap.

(Comparative example 3)
500.0 g (1.68 mol) of isostearic acid (Kroda Japan Ltd. Prisorine 3503, acid value 189 mg KOH / g) was added to a heating type kneading kneader attached with a thermometer, and the mixture was heated to 95 ° C. Thereto was added 1146.7 g (5.61 mol) of aluminum triisopropoxide (reagent grade 1 from Kishida Chemical Co., Ltd.), and the mixture was heated and kneaded. The reaction was stopped when distillation of isopropyl alcohol generated by the reaction ceased to give a viscous solid aluminum isostearate soap.

(Comparative example 4)
500.0 g (1.68 mol) of isostearic acid (Kroda Japan Ltd. Prisorine 3503, acid value 189 mg KOH / g) was added to a heating type kneading kneader attached with a thermometer, and the mixture was heated to 95 ° C. Thereto, 114.7 g (0.56 mol) of aluminum triisopropoxide (reagent grade 1 from Kishida Chemical Co., Ltd.) was added and heat-kneaded. The reaction was stopped when distillation of isopropyl alcohol generated by the reaction ceased to give a viscous solid aluminum isostearate soap.

(Comparative example 5)
In an 8 L separable flask, 300 g of isostearic acid (Croda Japan Ltd., Prisorine 3503, acid value of 189 mg KOH / g), and 2500 g of water were charged, and the temperature was raised to 60 ° C. Then, 48 mass% sodium hydroxide aqueous solution was 84.2
g was added, and the mixture was stirred at the same temperature (60 ° C.) for 1 hour to obtain an isostearic acid alkali compound salt aqueous solution. Thereafter, while maintaining at 60 ° C., 743.3 g of a 20% by mass aqueous solution of aluminum sulfate was added dropwise over 60 minutes to the aqueous solution of alkali isostearate compound salt. After completion of the dropwise addition, the mixture was kept at 60 ° C., stirred for 10 minutes and aged. 1500 g of water was added to the obtained aluminum isostearate soap aqueous solution slurry and cooled to 40 ° C. or less. Thereafter, the resultant was filtered with a suction filter, washed with water twice with 1000 g of water, and the obtained cake was dried with a tray drier to obtain an isostearic acid fatty acid aluminum soap.

(Comparative example 6)
In an 8 L separable flask, 300 g of stearic acid (Nippon Oil Co., Ltd. NAA-180, acid value 196 mg KOH / g), and 2500 g of water are charged, 60 ° C.
The temperature rose to the end. Subsequently, 84.2 g of 48 mass% sodium hydroxide aqueous solution was added, and it stirred at the same temperature (60 degreeC) for 1 hour, and the isostearic-acid alkali compound salt aqueous solution was obtained. Thereafter, while the temperature was maintained at 60 ° C., 1792.5 g of a 20% by mass aqueous solution of aluminum sulfate was added dropwise over 60 minutes to the aqueous solution of alkali isostearate compound salt. After completion of the dropwise addition, the mixture was kept at 60 ° C., stirred for 10 minutes and aged. 1500 g of water was added to the obtained aluminum isostearate soap aqueous solution slurry and cooled to 40 ° C. or less. After that, it is filtered by a suction filter and 1000
The resultant cake was washed with 2 g of water and dried in a tray drier to obtain an aluminum isostearate fatty acid aluminum soap.

<Mole ratio of acyl group to aluminum>
The molar ratio of acyl group to aluminum was measured as follows for each of the obtained aluminum soaps.
Hydrochloric acid was added to a predetermined amount of aluminum soap for acid decomposition, hexane was added to extract fatty acids, and the hexane layer was evaporated to dryness to quantify the amount of carboxylic acid. On the other hand, the amount of aluminum in the aqueous layer was quantified from atomic absorption spectrophotometry, and the molar ratio of the two was determined.

<Measured ash content>
About 1 g of the sample was precisely weighed in a porcelain crucible, and heated at a low temperature at first to volatilize volatile components, igniting the sample, heating it, and burning it until smoke disappeared. After being completely incinerated by holding in an electric furnace at 650 ° C. for 1 hour, it was taken out of the electric furnace, allowed to cool for 5 minutes, and then left in a desiccator for 60 minutes to precisely balance the ignition residue. It calculated from the following formula.

Measured ash content (%) = (ignition residue (g) / sample (g)) x 100

<Theoretical ash content>
It calculated by the following formula.

Theoretical ash content (%) = {102 / [78 + (M-18) x A]} x 100

·········· 102
· · · · · · · Molecular weight of aluminum hydroxide
M · · · · Molecular weight of the fatty acid used (56110 / acid number)
· · · · · · · Molar ratio of fatty acid to aluminum compound

<Solubility in hexane>
A predetermined amount of aluminum soap was added to hexane at 25 ° C., mixed with a stirrer, and the state after 1 hour was visually confirmed. The amount dissolved was taken as the measured value.

For each sample, using hydrogenated polyisobutylene (manufactured by NOF Corporation; Pearl Ream 6) as the liquid oil, the sample / liquid oil = 90/10 (mass ratio) and charged in a beaker in a predetermined amount, The mixture was heated and dissolved at ± 2 ° C to obtain a mixture. The solubility and the viscosity of the obtained sample were measured.
<Solubility>

Completely dissolved ... ○
Insoluble matter remains ... x

<Viscosity and rate of change in viscosity with temperature>
The measured value by a B-type viscometer at each predetermined temperature (25 ° C., 65 ° C.) and the rate of change of the viscosity at 65 ° C. to 25 ° C. were calculated.

Viscosity change rate = (25 ° C viscosity-65 ° C viscosity) / 25 ° C viscosity

  Raw materials of each example and comparative example, molar ratio of fatty acid to aluminum compound, molar ratio of acyl group to aluminum, measured ash content, theoretical ash content, A value, MFR, viscosity, measurement results of viscosity change rate Table 1, Table 2, shown in Table 3.

  As can be seen from Table 1, in the aluminum soap of the present invention example, by mixing with an organic solvent, it is possible to obtain a thickened material maintaining its transparency, and to make the viscosity change rate of the thickened material small. it can.

On the other hand, Comparative Example 1 (the aluminum compound described in JP-A-54-64645) had low solubility in hexane, and no thickening effect was observed for the liquid oil.
In Comparative Example 2, aluminum sulfate was used as the aluminum compound, the solubility in hexane was low, and no thickening effect was observed for the liquid oil.
In Comparative Example 3, the molar ratio of acyl group / aluminum was as low as 0.3 / 1, the solubility in hexane was low, and no thickening effect was observed for the liquid oil.

In Comparative Example 4, the molar ratio of acyl group / aluminum is as high as 3.0 / 1, which exceeds the upper limit of 2.5 of the present invention,
Although a certain thickening effect was observed for liquid oil, it did not have sufficient stability against temperature change of viscosity.
In Comparative Example 5, aluminum sulfate was used as the aluminum compound, the solubility in hexane was low, and no thickening effect was observed for the liquid oil.
In Comparative Example 6, aluminum sulfate was used as the aluminum compound, the solubility in hexane was low, and no thickening effect was observed for the liquid oil.

Claims (3)

An aluminum soap of a saturated fatty acid having 12 to 22 carbon atoms, wherein the molar ratio of acyl group derived from the saturated fatty acid to aluminum is 1.1 or more and 2.5 or less, and the solubility in hexane at 25 ° C. is 0 Aluminum soap characterized by having .5 g / L or more.
A liquid oil composition comprising the aluminum soap according to claim 1 and a liquid oil.
An aluminum soap by using a saturated fatty acid having 12 to 22 carbon atoms and an aluminum trialkoxide having 1 to 6 carbon atoms as a raw material, and reacting 1.4 to 2.7 moles of the saturated fatty acid with 1 mole of the aluminum trialkoxide. A method of producing an aluminum soap, characterized in that