JPH0745395B2 - Highly extensible glyceride composition - Google Patents

Description

TECHNICAL FIELD The present invention relates to a glyceride composition having high extensibility. More specifically, the present invention relates to a glyceride composition that imparts good elongation and light feel when used as an oily base for cosmetics or pharmaceuticals.

[Conventional technology]

In general, wax is used as a base for cosmetics, pharmaceuticals and the like, and its role is important, but conventionally used wax is not always satisfactory.
That is, since the wax used conventionally has a high melting point, an oily base having a low melting point and the wax having a high melting point must be mixed in order to impart extensibility. Further, since the wax has crystallinity, it causes a phenomenon such as separation of solid and liquid, crystallization of crystals, and sweating during the storage period, which significantly reduces the value of the product. In addition, commonly used wax is
Since it is mainly composed of very high-grade fatty acid or alcohol ester, it feels very heavy on the skin and does not spread well.

Various proposals have been made to remedy such drawbacks. For example, JP-B-60-20362 discloses a synthetic triglyceride obtained by esterifying a higher fatty acid and a glycerin each containing at least 30% by weight of a higher linear saturated fatty acid and a higher side chain saturated fatty acid, Japanese Patent Application Laid-Open No. 57-130909 discloses that a synthetic triglyceride containing behenic acid as an constituent fatty acid on average in an amount of 0.5 to 1.5 mol and a side chain saturated fatty acid having 8 or more carbon atoms in an amount of at least 1 mol on average improves the above-mentioned drawbacks. Proposed as an oily base for foods. However, since these synthetic triglycerides have high lipophilicity, they are sticky and are not sufficiently satisfactory in terms of improving the feel to the skin.

[Problems to be solved by the invention]

As shown above, even when conventionally used wax or synthetic triglyceride is used as an oily base for cosmetics, pharmaceuticals, etc., the product has a sufficient feeling of use, that is, a feeling of use, which is a performance necessary for the product. It was difficult.

It is an object of the present invention to solve the above-mentioned drawbacks of the prior art and to provide a glyceride composition which is amorphous, has good elongation, is non-greasy, and has a light feel on the skin. .

[Means for solving problems]

The present inventors have conducted extensive studies on a glyceride composition having properties that meet the above-mentioned object, and as a result, have found that a linear saturated fatty acid residue having 18 to 22 carbon atoms and a 2-ethylhexyl acid residue are contained in the molecule. 40 fatty acid diglycerides each with 1
The present invention has been completed by finding that a specific glyceride composition containing not less than wt% has desired properties and is suitable for the purpose of the present invention.

That is, the present invention relates to a linear saturated fatty acid having 18 to 22 carbon atoms and 2
-A glyceride composition obtained by esterification of ethylhexyl acid and glycerin, which comprises, as the main components, (a) a linear saturated fatty acid residue having 18 to 22 carbon atoms and a 2-ethylhexyl acid residue in the molecule, respectively. It contains 40 to 100% by weight of fatty acid diglyceride having one, and is another component. (B) Monoglyceride of linear saturated fatty acid having 18 to 22 carbon atoms and / or 2-ethylhexyl monoglyceride, (c) 18 carbon atoms ~ 22 linear diglyceride of saturated fatty acid, (d) 2-ethylhexyl diglyceride, and (e) triglyceride of linear saturated fatty acid having 18 to 22 carbon atoms, residual linear saturated fatty acid having 18 to 22 carbon atoms in the molecule Fatty acid triglycerides having two groups and one 2-ethylhexyl acid residue, one linear saturated fatty acid residue having 18 to 22 carbon atoms in the molecule and 2-ethylhexyl The content of one or more triglycerides selected from the group consisting of fatty acid triglycerides having two silic acid residues and 2-ethylhexyl triglyceride is (b) 10% by weight or less and (c) 20 respectively.
It relates to a glyceride composition having high extensibility suitable as a base material for cosmetics or a base material for pharmaceuticals, characterized in that the content is 10% by weight or less, (d) 10% by weight or less, and (e) 40% by weight or less. is there.

That is, the glyceride composition of the present invention has a carbon number in the molecule.
Synthetic diglyceride having one linear saturated fatty acid residue of 18 to 22 and one 2-ethylhexyl acid residue is 40% by weight or more, preferably 60% by weight based on the total glyceride composition.
It is a glyceride composition containing 99.6% by weight. Number of saturated carbon atoms for straight chain fatty acid composing diglyceride
Those in the range of 18 to 22, namely stearic acid, arachidic acid and behenic acid, show good extensibility and feel, and carbon number.
Fatty acids less than 18 are liquid or semi-liquid in the normal temperature range (10 to 30 ° C) and cannot be used as a solid component.
Further, it was found that among the 18 to 22 carbon atoms, behenic acid having 22 carbon atoms exhibits the best extensibility or feel in a wide temperature range from low temperature to room temperature (0 to 40 ° C). Therefore, behenic acid is most preferable as the linear fatty acid.

Another fatty acid that constitutes diglyceride is 2-ethylhexyl acid. Instead of 2-ethylhexylic acid, higher side chain fatty acids such as isostearic acid or lower to higher straight chain saturated fatty acids such as caprylic acid, lauric acid and palmitic acid, or unsaturated such as oleic acid, linoleic acid and pummitoleic acid. Even if a fatty acid is used, it does not show good extensibility, but shows a crystalline fragile property.

Diglycerides containing 18- to 22-carbon straight chain saturated fatty acids and 2-ethylhexylic acid as residues contain side chain fatty acid residues in the molecule, and thus have a wide molecular space and are non-crystalline. Indicates. That is, it exhibits a property of being semitransparent, elastic and rich in extensibility. The diglyceride is at room temperature (5 ℃ ~ 30
The crystal form by X-ray diffraction at (.degree. C.) was sub.alpha.

On the other hand, even diglycerides containing C18-C22 straight chain saturated fatty acids and side chain fatty acids as residues have higher side chain fatty acids (eg isostearic acid) as the residue No fragile crystals with no transparency. Its crystal form was α type.

Further, diglycerides containing a linear saturated fatty acid having 18 to 22 carbon atoms and other linear fatty acids or unsaturated fatty acids as residues did not show non-crystalline characteristics, and showed fragile crystals with no transparency. Its crystal form is β '(beta prime)
Or it was β type.

In a fatty acid diglyceride having one linear saturated fatty acid residue having 18 to 22 carbon atoms and one 2-ethylhexyl acid residue in the molecule, the content of the diglyceride is 40% or more in the glyceride composition (% is weight. (Standard, same below)
Is suitable, and when it is less than 40%, good elongation and feel of the glyceride composition are reduced. Further, the straight chain saturated fatty acid diglyceride having 18 to 22 carbon atoms is 20% or less based on the glyceride composition, and if it exceeds 20%, good elongation is impaired. Further, the diglyceride containing two 2-ethylhexyl acid residues, that is, 2-ethylhexyl diglyceride, needs to be 10% or less based on the glyceride composition, and if it is more than 10%, good elongation is impaired. Be done.

Further, in the process of producing a fatty acid diglyceride having one linear saturated fatty acid residue having 18 to 22 carbon atoms and one 2-ethylhexyl acid residue in the molecule, which is important in the present invention, monoglyceride and triglyceride other than diglyceride are Although they are produced, they need to be removed as much as possible by purification. In particular, the content of monoglyceride is required to be 10% or less because it adversely affects both the good elongation and the good feel that are characteristic of the fatty acid diglyceride. Further, in triglyceride, although the effect on the extensibility is small, if the content is increased, the feel becomes heavy, so the content must be 40% or less.

In addition, a linear saturated fatty acid residue having 18 to 22 carbon atoms in the molecule and 2
-The glyceride composition of the present invention containing 40 wt% or more of a fatty acid diglyceride having an ethylhexyl acid residue has a solid fat content (NMR) at room temperature (0 ° C to 35 ° C).
Law; established by Japan Oil Chemistry Association, measured by inclusion of a temporary solid fat)
Is preferably 50% or more.

The glyceride composition of the present invention is produced by esterifying a linear saturated fatty acid having 18 to 22 carbon atoms, 2-ethylhexyl acid and glycerin by a known method. For esterification,
A method using an acid halide, a transesterification method, a method without a catalyst and an esterification reaction under normal pressure or reduced pressure in the presence of a catalyst can be used.

The excess monoglyceride formed during the esterification reaction can be removed by a molecular distillation method or a chromatography method, and a linear saturated fatty acid residue having 18 to 22 carbon atoms and a 2-ethylhexyl acid residue are respectively contained in the molecule. The composition containing one fatty acid diglyceride can be concentrated by a solvent extraction method, a solvent fractionation method (molecular distillation method, etc.).

The glyceride composition thus obtained is decolorized and deodorized according to a conventional method to give a colorless and odorless glyceride composition which does not irritate the skin and has excellent elongation and good non-crystallinity. It has excellent properties as a solid oily base for cosmetics, pharmaceuticals and the like.

The effects will be described in detail in the following examples, but the present invention is not limited to these examples.

〔Example〕

Examples of the glyceride composition according to the present invention are shown below,
The present invention will be described in more detail.

Examples 1 and 2, and Comparative Examples 1 to 4 0.4 mol% of glycerin 1 mol, fatty acid (A) 1 mol, fatty acid (B) 1 mol and activated carbon relative to the total amount charged.
In addition, the reaction was carried out at 150 to 260 ° C until the amount of water produced by esterification reached the calculated amount. The time required was 2 to 4 hours, and 90 to 100% of the calculated amount of water separated. Then, to remove unreacted glycerin and fatty acids, 150 ~ 200 ℃
After steam distillation for 1 hour, the activated carbon was removed by filtration to obtain a glyceride composition A.

Further, the glyceride composition A was concentrated with silica gel column chromatography to diglyceride, and the diglyceride was subjected to solvent fractionation using 5 times by weight of n-hexane to obtain a medium melting point composition. It was

The fatty acids (A) and fatty acids (B) used were the fatty acids shown in Table 1.

Similarly, Table 1 shows the composition of the medium melting point composition finally obtained by solvent fractionation.

Using this medium melting point concentrate, the following extensibility was evaluated.

<Evaluation of extensibility> i) Sensory evaluation: The glyceride composition is arranged into a column having a length of 1 cm and a diameter of 1 cm, and a glass plate having a piece of 3 cm is laid on the cylinder, and 1 is placed on the glass plate.
After placing a weight of 0 kg and crushing the glyceride composition, the condition of the outer ring was observed. The evaluation was performed at 5 to 40 ° C.

Evaluation criteria ii) Measurement of stress relaxation rate: Rheometer NRM-201 manufactured by Fudo Kogyo Co., Ltd.
The stress relaxation rate was determined at 0 to 40 ° C using 0J-CW. A material having a high stress relaxation rate is a solid material having a good elongation.

Specifically, arrange the sample into a cylindrical shape with a diameter of 1 cm and a height of 1 cm,
On top of that, put a glass plate with a piece of 3 cm underneath, 10k from above
A load of g was applied, and when the stress reached 10 kg, the load was removed, and the rate of change in stress thereafter was measured.

Table 2 shows the evaluation results of the extensibility of Examples 1 and 2 and Comparative Examples 1 to 4.

As is clear from Table-2, it is understood that the glyceride composition whose main constituent is diglyceride, in which the fatty acid constituting glyceride is behenic acid and 2-ethylhexyl acid, exhibits good elongation in a wide temperature range.

It can also be seen that a glyceride composition mainly composed of diglyceride, which is a fatty acid constituting glyceride and is composed of stearic acid and 2-ethylhexylic acid, also exhibits good elongation at room temperature (20 ° C.) or lower.

On the other hand, the glyceride compositions of Comparative Examples 1 to 4 have brittleness of crystals, such as cracking when crushed, and thus cannot be said to have good elongation.

Examples 3 to 4, and Comparative Examples 5 to 9 1 mol of glycerin, 1 mol of behenic acid, 1 mol of 2-ethylhexylic acid and 0.4% by weight of activated carbon were added to the whole charged amount, and esterification was carried out at 150 to 260 ° C. The reaction was performed until the calculated amount of water generated by The time required is 3 hours,
98% of the calculated amount of water separated. Next, after removing the activated carbon by filtration, unreacted glycerin and fatty acid were removed by molecular distillation to obtain a glyceride composition B (Comparative Example 5).

Further, n-hexane was added to the glyceride composition B in an amount of 4 times the weight of the glyceride composition B, and solvent fractionation was performed to obtain a glyceride composition C (Example 3) as an intermediate melting point fraction.

The low melting point fraction was further removed by molecularly distilling the glyceride composition C to obtain a glyceride composition D (Example 4).

N-Hexane was added to glyceride composition B in an amount of 4 times the weight of glyceride composition B, and solvent fractionation was performed to remove the high melting point fraction. Glyceride composition E (Comparative Example 6) was used as a medium and low melting point fraction. Obtained. N-hexane was added to glyceride composition B in an amount of 4 times the weight of glyceride composition B, and solvent fractionation was performed to remove the low melting point fraction, and glyceride composition F (Comparative Example 7) was used as the high and medium melting point fractions. Obtained.

Acetone was added to the glyceride composition B four times as much as the glyceride composition B, and solvent fractionation was performed to obtain a glyceride composition G (Comparative Example 8) as a medium melting point fraction.

Glycerin (1 mol), behenic acid (1.25 mol), 2-ethylhexyric acid (1.25 mol) and activated carbon (0.4% by weight) were added to the whole amount of the mixture, and the reaction was carried out at 150 to 260 ° C until the amount of water produced by esterification reached the calculated amount. . It took 4 hours and 95% of the calculated water was separated. Next, after removing the activated carbon by filtration, unreacted glycerin and fatty acid were removed by molecular distillation to obtain a glyceride composition H.

Further, n-hexane was added to the glyceride composition H in an amount of 4 times the weight of the glyceride composition H, and solvent fractionation was performed to obtain a glyceride composition I (Comparative Example 9) as an intermediate melting point fraction.

Examples 3 to 4 and Comparative Examples 5 obtained as described above
The composition of the glyceride composition of 9 is shown in Table-3.

Further, each composition was evaluated for extensibility and touch. The extensibility was evaluated in Example 1 at 20 ° C.
The same method as described in (1) above was used, and the feel was evaluated by the following method.

<Sensory Evaluation of Feeling> 50 parts by weight of each glyceride composition was mixed with 50 parts by weight of petrolatum, dissolved at 70 ° C., and then cooled to room temperature,
Evaluation was carried out by applying 1 g to the upper arm.

Evaluation criteria The evaluation results are shown in Table-3.

As is clear from Table 3, Example 3 and Example 4 in which the composition range of the glyceride composition is within the specific condition range of the present invention
It can be seen that, while having excellent elongation and excellent feel, the comparative example outside the condition range of the present invention has no elongation or has a heavy feel.

〔The invention's effect〕

As shown above, the glyceride composition of the present invention is excellent in elongation, has a smooth and non-greasy feel, and is chemically stable. Therefore, it is extremely suitable and useful as an oily base for cosmetics or pharmaceuticals. It is something.

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Claims (1)

[Claims] 1. A glyceride composition obtained by esterification of a linear saturated fatty acid having 18 to 22 carbon atoms and 2-ethylhexylic acid with glycerin, which comprises, as a main component, (a) having 18 to 18 carbon atoms in the molecule. (B) a linear saturated fatty acid having 18 to 22 carbon atoms, which contains 40 to 100% by weight of a fatty acid diglyceride having one linear saturated fatty acid residue of 22 and one 2-ethylhexylic acid residue, respectively. Monoglyceride or / and 2-ethylhexyl monoglyceride, (c) diglyceride of linear saturated fatty acid having 18 to 22 carbon atoms, (d) 2-ethylhexyl diglyceride, and (e) linear saturated fatty acid having 18 to 22 carbon atoms Triglyceride, fatty acid triglyceride having two linear saturated fatty acid residues having 18 to 22 carbon atoms and one 2-ethylhexyl acid residue in the molecule, carbon number in the molecule The content of one or more triglycerides selected from the group consisting of fatty acid triglycerides having one linear saturated fatty acid residue of 18 to 22 and two 2-ethylhexyl acid residues and 2-ethylhexyl acid triglyceride is , (B) 10 wt% or less, (c) 20
A glyceride composition having a high extensibility suitable as a base material for cosmetics or a base material for pharmaceuticals, characterized in that the content is 10% by weight or less, (d) 10% by weight or less, and (e) 40% by weight or less.