Preservatives and storage methods for glycerol monofatty acid esters or polyglycerol monofatty acid esters

Abstract

To provide a stabilizer for glycerin mono-fatty acid ester or polyglycerin mono-fatty acid ester, and a stabilization method.SOLUTION: Provided is a stabilizer for stabilizing the purity of a glycerin mono-fatty acid ester or polyglycerin mono-fatty acid ester having a monoester purity of 85 mass% or more. The stabilizer comprises a polyhydric alcohol having 3 to 10 carbon atoms and 2 to 6 valences.SELECTED DRAWING: None

Description

Technical Field

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[0001] The present invention relates to agents and storage methods of glycerol monofatty acid esters or polyglycerol monofatty acid esters. storage

Background Art

[0002] Glycerol monofatty acid esters or polyglycerol monofatty acid esters are used in various products ranging from lipid processed foods to cosmetics and pharmaceuticals. Among them, the monoester form has high emulsifying performance and is widely used as an emulsifier for cosmetics and foods. However, there has been a problem that diglycerides and triglycerides are generated over time, resulting in a decrease in the purity of the monoester and a decrease in the emulsifying performance.

[0003] Therefore, a method of suppressing the decrease in purity by storing at low temperature has been taken. However, due to the limited storage space and the difficulty during transportation, a simple method that can be stored even at room temperature has been desired. <00000!6>

[0004] As a method for stabilizing esters, for example, Patent Document 1 provides a stabilization method in which an alcohol corresponding to an ester group is added to a glycolic acid ester containing water in a predetermined ratio.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] However, while the method described in Patent Document 1 can prevent the decomposition of esters by hydrolysis, it does not prevent the formation of diglycerides or triglycerides. For this reason, no method has been proposed to prevent the decrease in monoester purity over time and to stabilize it.

[0007] The object of the present invention is glycerol monofatty acid ester or polyglycerol monofatty acid ester storage Agents and storage The goal is to provide a method. [Means for solving the problem]

[0008] The inventors of this invention are as follows: (1) Glycerin mono fatty acid ester and / or polyglycerin mono fatty acid ester having a monoester purity of 85% by mass or more A preservative for suppressing the decrease in the purity of the monoester when stored at temperatures between 0°C and 50°C, by mixing the preservative at room temperature. And, A glycerol monofatty acid ester or polyglycerol monofatty acid ester characterized by comprising a polyhydric alcohol having 3 to 10 carbon atoms and a valency of 2 to 6. Preservative . (2) The glycerol mono fatty acid ester and / or the polyglycerol mono fatty acid ester, (1) Preservative of Mix at room temperature In this case, the glycerol monofatty acid ester, the polyglycerol monofatty acid ester and the Preservative When the total amount is taken as 100% by mass, the above Preservative A glycerin monofatty acid ester or polyglycerin monofatty acid ester characterized in that the mass of is 5% by mass or more and 40% by mass or less. storage method. [Effects of the Invention]

[0009] According to the present invention, glycerol monofatty acid ester or polyglycerol monofatty acid ester During storage This can suppress the decrease in purity. [Modes for carrying out the invention]

[0010] In this specification, numerical ranges defined using the symbol "~" include the numbers at both ends (upper and lower limits) of "~". For example, "2~5" means 2 or greater and 5 or less.

[0011] (Glycerin mono fatty acid ester) The glycerol monofatty acid ester used in the present invention mainly consists of monoesters, but may also contain triesters and diesters in part. However, a monoester is a monoglyceride obtained by esterifying one molecule of fatty acid to glycerol, a diester is a diglyceride obtained by esterifying two molecules of fatty acid to glycerol, and a triester is a triglyceride obtained by esterifying three molecules of fatty acid to glycerol.

[0012] When the monoglyceride content (purity) of the glycerin fatty acid ester is low, the monoglyceride can remain relatively stable even if left standing without the addition of a stabilizer, resulting in less degradation of purity. Therefore, the glycerin fatty acid ester used in this invention has a monoester purity of 85% by mass or more, preferably 90% by mass or more, most preferably 95% by mass or more, and may also be 100% by mass.

[0013] The fatty acids constituting the glycerol fatty acid ester are not particularly limited, but may be saturated fatty acids, monounsaturated fatty acids, or polyunsaturated fatty acids, and are more preferably saturated fatty acids or monounsaturated fatty acids. Furthermore, the number of carbon atoms in the fatty acid is preferably 8 or more, more preferably 12 or more. Also, the number of carbon atoms in the fatty acid is preferably 24 or less, and more preferably 22 or less. These fatty acids include capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, linoleic acid, Behenic acid and the like are preferred, and lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, linoleic acid, behenic acid and the like are preferred, and isostearic acid and oleic acid are particularly preferred.

[0014] The method for producing the glycerin fatty acid ester is not particularly limited, and the following can be exemplified. (a) Esterification reaction of fatty acid and glycerin (b) Transesterification reaction of glycerin fatty acid ester such as fats and oils and glycerin (c) Ring-opening reaction of glycidol and fatty acid

[0015] (Polyglycerin monofatty acid ester) The polyglycerin fatty acid ester used in the present invention is an ester of polyglycerin having a polymerization degree of 2 or more and a fatty acid. This mainly consists of monoesters and may partly contain triesters and diesters. However, the monoesters are monoesters obtained by ester-bonding one molecule of fatty acid to polyglycerin, the diesters are diesters obtained by ester-bonding two molecules of fatty acid to polyglycerin, and the triesters are triesters obtained by ester-bonding three molecules of fatty acid to polyglycerin.

[0016] When the content ratio (purity) of the monoesters in the polyglycerin fatty acid ester is low, the purity decrease over time is small without adding a stabilizer, and the monoesters can exist relatively stably. Therefore, the polyglycerin monofatty acid ester used in the present invention has a monoesters purity of 85% by mass or more, preferably 90% by mass or more, most preferably 95% by mass or more, and may be 100% by mass.

[0017] The number of structural units (-OCH2CH(OH)CH2-) derived from glycerin contained in the polyglycerin fatty acid ester used in the present invention is not particularly limited, but from the viewpoint of the action and effect of the present invention of stabilizing the monoesters, it is preferably 4 or more and preferably 12 or less.

[0018] The fatty acids constituting the polyglycerol fatty acid ester are not particularly limited, and may be saturated fatty acids, monounsaturated fatty acids, or polyunsaturated fatty acids, and it is more preferable that they are saturated fatty acids or monounsaturated fatty acids. Further, the number of carbon atoms of the fatty acid is preferably 8 or more, more preferably 12 or more. Further, the number of carbon atoms of the fatty acid is preferably 24 or less, more preferably 22 or less. Examples of such fatty acids include capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, linoleic acid, behenic acid, etc., are preferable, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, linoleic acid, behenic acid, etc. are preferable, and isostearic acid and oleic acid are particularly preferable.

[0019] The method for producing the polyglycerol fatty acid ester is not particularly limited, and the following can be exemplified. (a) Esterification reaction of polyglycerol and fatty acid (b) Transesterification reaction of polyglycerol and fatty acid ester (c) Transesterification reaction of polyglycerol and oil or fat

[0020] (Stabilizer) The stabilizer in the present invention is a polyhydric alcohol having 3 to 10 carbon atoms and a valence of 2 to 6. The number of carbon atoms of this polyhydric alcohol is more preferably 6 or less, particularly preferably 4 or less. The most preferable number of carbon atoms of the polyhydric alcohol is 3. Further, the valence (number of hydroxyl groups) of the polyhydric alcohol is more preferably 3 or more, and more preferably 4 or less. The most preferable valence (number of hydroxyl groups) of the polyhydric alcohol is 3.

[0021] Examples of such polyhydric alcohols include glycerin, 1,3-butylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, diglycerin, triglycerin, etc. Among these, glycerin, 1,3-butylene glycol, and propylene glycol are preferable, and glycerin is most preferable.

[0022] (Stabilization method) In the stabilization method of the present invention, the stabilizer of the present invention is mixed with a glycerin monofatty acid ester and / or a polyglycerin monofatty acid ester. When the total amount of the glycerin monofatty acid ester, polyglycerin monofatty acid ester and stabilizer is 100% by mass, the mass of the stabilizer is set to 5% by mass or more and 40% by mass or less. This provides a particularly remarkable stabilization effect. From this viewpoint, the mass of the stabilizer is preferably 10% by mass or more, and more preferably 15% by mass or more. Furthermore, the mass of the stabilizer is preferably 30% by mass or less, and more preferably 25% by mass or less.

[0023] In this stabilization method, the storage temperature of the mixture is 0 to 50°C. However 0 to 40°C is more preferable, and 4 to 30°C is most preferable. When the temperature is below 0°C, the decrease in purity of the monoglyceride over time is relatively small even without adding a stabilizer, so the effects of the present invention are particularly pronounced in the temperature range of 0°C or above. [Examples]

[0024] Accelerated testing was conducted to confirm the effect of the stabilizer. Specifically, the (A) glycerin monofatty acid ester or polyglycerin monofatty acid ester and stabilizer (B) or (B') shown in Tables 1 and 2 were mixed in the respective mass ratios shown in Tables 1 and 2 to obtain the mixtures. The total amount of (A) and (B) or (B') was 100% by mass. The monoester purity of (A) glycerin monofatty acid ester and polyglycerin monofatty acid ester was 98.0% by mass. The raw materials were blended according to the compositions shown in Tables 1 and 2 and mixed at room temperature until homogeneous to obtain each mixture.

[0025] (A) The monoester purity of glycerol monofatty acid esters and polyglycerol monofatty acid esters decreases over time. Therefore, an accelerated test was performed by storing both the example mixture and the comparative example mixture in a constant temperature bath at 50°C for 60 days. The monoester purity of the example mixture and the comparative example mixture was measured before and after the accelerated test by gel permeation chromatography (GPC). From the measured purity, the stability of the monoester purity was calculated using the following formula. Stability of monoester purity (%) = (Monoester purity immediately after accelerated testing / Monoester purity immediately before accelerated testing) × 100

[0026] The stability of the monoester purity was evaluated according to the following criteria. ◎: Monoester purity stability of 85% or higher ○: Monoester purity stability is 75% or higher, but less than 85%. △: Monoester purity stability is 65% or higher, but less than 75%. ×: Monoester purity stability is less than 65%

[0027] [Table 1]

[0028] [Table 2]

[0029] Examples 1 to 9 show that when the stabilizer of the present invention was added, the monoester purity remained high and stability was excellent even after accelerated testing.

[0030] In contrast, as is clear from Comparative Examples 1 to 3, when the stabilizer of the present invention was not added, the monoester purity decreased significantly over time. In Comparative Example 4, "PEG-400" (polyethylene glycol) was added as a stabilizer, but the monoester purity still decreased significantly. Furthermore, in Comparative Example 5, oleyl alcohol was added as a stabilizer, but the monoester purity still decreased significantly.

Claims

1. A preservative for suppressing the decrease in monoester purity when storing glycerin monofatty acid esters and / or polyglycerin monofatty acid esters having a monoester purity of 85% by mass or more at a temperature of 0°C or higher and 50°C or lower, by mixing the preservative at room temperature, A preservative for glycerol monofatty acid esters or polyglycerol monofatty acid esters, characterized by comprising a polyhydric alcohol having 3 to 10 carbon atoms and a valency of 2 to 6.

2. A method for storing a glycerin monofatty acid ester or a polyglycerin monofatty acid ester, characterized in that the preservative described in claim 1 is mixed with the glycerin monofatty acid ester and / or the polyglycerin monofatty acid ester at room temperature, wherein when the total amount of the glycerin monofatty acid ester, the polyglycerin monofatty acid ester and the preservative is 100% by mass, the mass of the preservative is 5% by mass or more and 40% by mass or less.

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