CN113527662A - Preparation method and application of oily thickener - Google Patents

Preparation method and application of oily thickener Download PDF

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CN113527662A
CN113527662A CN202110958515.2A CN202110958515A CN113527662A CN 113527662 A CN113527662 A CN 113527662A CN 202110958515 A CN202110958515 A CN 202110958515A CN 113527662 A CN113527662 A CN 113527662A
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acid
thickener
reaction
oil phase
fatty acid
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邢鹏遥
郝爱友
安伟
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Shandong Binzhou Gin&ing New Material Technology Co ltd
Shandong University
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Shandong Binzhou Gin&ing New Material Technology Co ltd
Shandong University
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/46—Post-polymerisation treatment, e.g. recovery, purification, drying
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
    • C08G2650/04—End-capping

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  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
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  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

The invention relates to a preparation method of an oily thickener, which comprises the steps of mixing polyglycerol with a hydroxyl value of 800-1000-substituted polyglycerol with long-chain fatty acid and 12-hydroxystearic acid, reacting under a vacuum condition until the acid value is less than 2, and cooling to room temperature for forming to obtain a finished product. The invention synthesizes the polyglyceryl fatty acid ester oily thickener by the polyglyceryl with a specific structure, specific fatty acid and 12-hydroxystearic acid. All raw materials are from natural plants, the final product has good biodegradability, and can be used as a thickener to be added into the oil phase of the cosmetic, and when the addition amount of the thickener is 4-6% of the mass of the oil phase, the oil phase forms a gel state at room temperature; can obviously change the rheological property of the oil phase, has obvious performance and has good application prospect in the cosmetic paste product.

Description

Preparation method and application of oily thickener
Technical Field
The invention relates to a preparation method and application of an oily thickener, belonging to the technical field of fine chemical synthesis.
Background
The thickening agent is a rheological additive, can enhance the consistency of a system, and is widely applied to cosmetics, foods and chemical industry. Thickeners can be divided into oily thickeners and aqueous thickeners. The aqueous thickening agent is common and can be divided into a low molecular thickening agent and a high molecular thickening agent, wherein CMC, xanthan gum, polyacrylic acid polymers (Chinese name carbomer) and the like are widely applied.
Oily thickeners are relatively few compared to aqueous thickeners. Oily thickening can be achieved with high viscosity polyisobutylene or fumed silica. But polyisobutylene is poorly degradable; the system formed by the fumed silica has pseudoplasticity and needs special attention during operation. The palmitic acid dextrin ester and the myristic acid dextrin produced by Japan Qianye powder manufacturing company can obviously change the rheological property of an oil phase, are oily thickening substances with excellent performance, and have higher application value in cosmetics. But the production process is complex, the post-treatment is difficult and the production cost is very high.
Chinese patent document CN112188885A discloses an oil-based thickener for cosmetic materials, which is an oil-soluble copolymer composed of a monomer unit composed of a hydrophilic monomer, a monomer unit composed of a hydrophobic monomer that is easily crystallized, and a monomer unit composed of a hydrophobic monomer that is hardly crystallized. The thickener can thicken various oil phases, but the production process is complex, more organic solvents are adopted in the production process, and the post-treatment is complex.
Therefore, it is necessary to develop a thickener with remarkable effect, moderate cost, good degradability and good biocompatibility so as to widen the range of oily thickeners.
The polyglycerol fatty acid ester is a biodegradable multifunctional material obtained by taking natural plant-based glycerol and fatty acid as raw materials, can obtain products with various functions by adjusting the polymerization degree, the fatty acid type and the esterification degree of polyglycerol, and meets various requirements; however, the conventional polyglycerin fatty acid ester is weak in oily thickening or can exert a thickening effect only when the amount of addition is high, and the amount of addition is large and the cost is high.
Disclosure of Invention
Aiming at the defects of the prior art, in particular to the problems of weak thickening effect, large addition amount, high cost and the like of the existing polyglycerol fatty acid ester oily thickening agent, the invention provides a preparation method and application of an oily thickening agent.
In order to realize the purpose, the invention is realized by the following technical scheme:
a preparation method of an oily thickener comprises the following steps:
mixing polyglycerol with hydroxyl value of 800-1000 with long-chain fatty acid and 12-hydroxystearic acid, reacting under vacuum condition until the acid value is less than 2, and cooling to room temperature for molding to obtain the finished product.
Preferably, the hydroxyl number of the polyglycerol according to the invention is 850-950.
Preferably, according to the invention, the long chain fatty acid is stearic acid and/or behenic acid.
More preferably, the long chain fatty acid is a mixture of stearic acid and behenic acid, and the stearic acid in the mixture is more than 65% pure stearic acid, and further more preferably, the stearic acid is more than 90% pure stearic acid. The mass ratio of stearic acid to behenic acid is 1-2: 2-1.
Preferably, according to the invention, the ratio of the mass of polyglycerol to the total mass of long-chain fatty acid and 12-hydroxystearic acid is 100: 300-450.
Further preferably, the ratio of the mass of the polyglycerol to the total mass of the long-chain fatty acid and the 12-hydroxystearic acid is 150: 350-420.
According to the invention, the mass ratio of the long-chain fatty acid to the 12-hydroxystearic acid is preferably 3:2 to 1: 3.
Further preferably, the mass ratio of the long-chain fatty acid to the 12-hydroxystearic acid is 1:1 to 1: 2.
Preferably, according to the invention, the vacuum reaction pressure is from-0.08 to-0.04 MPa.
Preferably, according to the invention, the vacuum reaction temperature is 180-220 ℃.
According to the invention, preferably, during the vacuum reaction, an esterification catalyst is added for reaction, when the system is in a homogeneous state, sampling detection is carried out, when the acid value is less than 2, the reaction is stopped, the reaction system is naturally cooled to below 90 ℃, and materials are discharged.
Further preferably, the esterification catalyst is p-toluenesulfonic acid, potassium hydroxide or butyl titanate.
The hydroxyl value can be measured by a pyridine acetic anhydride method, and the unit is mg KOH/g; the acid number can be determined by titration with a standard solution of potassium hydroxide, using phenolphthalein as an indicator, in mg KOH/g.
An oily thickener is prepared by the method.
The obtained oily thickener can be used as thickener to be added into cosmetic oil phase, and when the addition amount of the thickener is 4-6% of the oil phase mass, the oil phase forms gel state at room temperature.
Preferably, according to the invention, the cosmetic oil phase is paraffin oil, olive oil or caprylocaprate.
The oily thickener is added into the oil phase of the cosmetic as the thickener, the oil phase can form a gel state at room temperature, the performance is outstanding, the oily thickener can provide supporting force when being added into a common oily system of the cosmetic, and the strength and the toughness of the paste are obviously improved.
The invention has the beneficial effects that:
1. the invention synthesizes the polyglyceryl fatty acid ester oily thickener by polyglyceryl with a specific structure, specific long-chain fatty acid and 12-hydroxystearic acid. All raw materials are from natural plants, and the final product has good biodegradability and accords with the current concept of sustainable development.
2. Compared with the prior art, the production process of the oily thickener is simpler and more convenient, and the oily thickener is convenient for industrialization.
3. The oily thickener prepared by the invention is used as a thickener to be added into the oil phase of cosmetics, and when the addition amount of the thickener is 4-6% of the mass of the oil phase, the oil phase forms a gel state at room temperature; can obviously change the rheological property of the oil phase, has obvious performance and has good application prospect in the cosmetic paste product.
Drawings
FIG. 1 shows an oily thickener obtained in example 81H-NMR spectrum;
FIG. 2 shows an oily thickener obtained in example 813C-NMR spectrum.
Detailed Description
The present invention will be further described with reference to the following detailed description of embodiments thereof, but not limited thereto, in conjunction with the accompanying drawings.
The starting materials used in the examples are all conventional commercial products.
Examples 1,
The preparation method of the oily thickener comprises the following steps:
100g of polyglycerol (hydroxyl value 945), 200g of stearic acid (stearic acid purity is 92 percent) and 200g of 12-hydroxystearic acid are added into a 1L reaction kettle, then 0.45g of potassium hydroxide is added as a catalyst, the temperature is raised to 200 ℃ for reaction, the reaction system is in a homogeneous transparent state after 2 hours of reaction under the vacuum condition of the pressure of-0.06 Mpa, and the acid value of the product is measured to be 0.8 by sampling. And naturally cooling the system to 90 ℃, discharging, and cooling to room temperature to obtain a product which is a light yellow solid.
Example 2
The preparation method of the oily thickener comprises the following steps:
100g of polyglycerol (hydroxyl value 970), 200g of stearic acid (stearic acid purity is 65%) and 200g of 12-hydroxystearic acid are added into a 1L reaction kettle, 0.5g of potassium hydroxide is added as a catalyst, the temperature is raised to 200 ℃ for reaction, the reaction system is in a homogeneous transparent state after 2 hours of reaction under the vacuum condition of-0.08 Mpa, and the acid value of a product is 1.5 by sampling. Naturally cooling the system to 90 ℃, and discharging. Cooled to room temperature and the product was a pale yellow solid.
Example 3
The preparation method of the oily thickener comprises the following steps:
100g of polyglycerol (hydroxyl value 880), 100g of behenic acid (stearic acid purity is 90 percent) and 300g of 12-hydroxystearic acid are added into a 1L reaction kettle, then 0.5g of potassium hydroxide is added as a catalyst, the temperature is raised to 210 ℃ for reaction, the reaction is carried out for 3 hours under the vacuum condition of the pressure of-0.095 Mpa, the reaction system is in a homogeneous transparent state after 2 hours of reaction, and the acid value of the product is 1.5 by sampling. Naturally cooling the system to 90 ℃, and discharging. Cooled to room temperature and the product was a pale yellow solid.
Example 4
The preparation method of the oily thickener comprises the following steps:
100g of polyglycerol (hydroxyl value 865), 130g of stearic acid (stearic acid with the purity of 92 percent) and 230g of 12-hydroxystearic acid are added into a 1L reaction kettle, then 0.5g of potassium hydroxide is added as a catalyst, the temperature is raised to 215 ℃ for reaction, the reaction system is in a homogeneous transparent state after the reaction is carried out for 2 hours under the vacuum condition of the pressure of-0.075 Mpa after the reaction is carried out for 3 hours, and the acid value of the product is measured to be 1.8 by sampling. Naturally cooling the system to 90 ℃, and discharging. Cooled to room temperature and the product was a pale yellow solid.
Example 5
The preparation method of the oily thickener comprises the following steps:
100g of polyglycerol (hydroxyl value 900), 130g of stearic acid (stearic acid purity is 65%) and 230g of 12-hydroxystearic acid are added into a 1L reaction kettle, 0.5g of potassium hydroxide is added as a catalyst, the temperature is increased to 215 ℃ for reaction, the reaction system is in a homogeneous transparent state after reaction for 2 hours under the vacuum condition of-0.075 Mpa after reaction for 3 hours, and the acid value of the product is 1.4 by sampling. Naturally cooling the system to 90 ℃, and discharging. Cooled to room temperature and the product was a pale yellow solid.
Example 6
The preparation method of the oily thickener comprises the following steps:
100g of polyglycerol (hydroxyl value 900), 80g of stearic acid (stearic acid purity is 65%), 40g of behenic acid (behenic acid content is 90%) and 230g of 12-hydroxystearic acid are added into a 1L reaction kettle, then 0.5g of potassium hydroxide is added as a catalyst, the temperature is increased to 215 ℃ for reaction, the reaction is carried out under the vacuum condition of-0.075 Mpa for 3 hours, the reaction system is in a homogeneous transparent state after 2 hours of reaction, and the acid value of the product is 1.4 by sampling. Naturally cooling the system to 90 ℃, and discharging. Cooled to room temperature and the product was a pale yellow solid.
Example 7
The preparation method of the oily thickener comprises the following steps:
100g of polyglycerol (hydroxyl value 930), 80g of stearic acid (stearic acid purity is 65%), 40g of behenic acid (behenic acid content is 90%) and 230g of 12-hydroxystearic acid are added into a 1L reaction kettle, then 0.5g of butyl titanate is added as a catalyst, the temperature is raised to 235 ℃ for reaction, the reaction is carried out under the vacuum condition of-0.075 Mpa for 3 hours, the reaction system is in a homogeneous transparent state after 2 hours of reaction, and the acid value of the product is 1.2 by sampling. Naturally cooling the system to 90 ℃, and discharging. Cooled to room temperature and the product was a pale yellow solid.
Example 8
The preparation method of the oily thickener comprises the following steps:
100g of polyglycerol (hydroxyl value 930), 80g of stearic acid (stearic acid purity is 65%), 80g of behenic acid (behenic acid content is 90%) and 160g of 12-hydroxystearic acid are added into a 1L reaction kettle, then 0.5g of p-toluenesulfonic acid is added as a catalyst, the temperature is raised to 175 ℃ for reaction, the reaction is carried out under the vacuum condition of the pressure of-0.075 Mpa for 3 hours, the reaction system is in a homogeneous transparent state after 2 hours of reaction, and the acid value of the product is 1.4 by sampling. Naturally cooling the system to 90 ℃, and discharging. Cooled to room temperature and the product was a pale yellow solid.
Preparation of oily thickener obtained in this example 81The H-NMR spectrum is shown in FIG. 1,13the C-NMR spectrum is shown in FIG. 2.
As confirmed by a hydrogen spectrum and a carbon spectrum, a peak at a chemical shift of 3.5 to 5.5 is a peak of polyglycerin H, a peak around 0.9 is a peak of methyl H of a fatty acid, and a peak of 1.0 to 2.0 is CH of a fatty acid2The upper H peak, about 2.5, is the peak of hydrogen at C bonded to the ester bond.
Example 9
The oily thickener prepared in example 1 is used as a thickener, and when the addition amount of the thickener is 5% of the mass of the oil phase, the oil phase forms a gel state at room temperature; the cosmetic oil phase is paraffin oil, olive oil or glyceryl caprylic capric acid ester.
Comparative example 1
The preparation method of the oily thickener comprises the following steps:
100g of polyglycerol (hydroxyl value of 1235), 80g of stearic acid (stearic acid purity of 65%), 80g of behenic acid (behenic acid content of 90%) and 160g of 12-hydroxystearic acid are added into a 1L reaction kettle, then 0.5g of p-toluenesulfonic acid is added as a catalyst, the temperature is raised to 175 ℃ for reaction, the pressure is-0.075 Mpa, after 3 hours of reaction, the reaction system is in a homogeneous transparent state after 2 hours of reaction, and the acid value of the product is 1.4 by sampling. Naturally cooling the system to 90 ℃, and discharging. Cooled to room temperature and the product was a pale yellow solid.
Comparative example 2
The preparation method of the oily thickener comprises the following steps:
100g of polyglycerol (hydroxyl value 950), 160g of lauric acid and 160g of 12-hydroxystearic acid are added into a 1L reaction kettle, then 0.5g of p-toluenesulfonic acid is added as a catalyst, the temperature is raised to 175 ℃ for reaction, the pressure is-0.075 Mpa, after 3 hours of reaction, after 2 hours of reaction, the reaction system is in a homogeneous transparent state, and the acid value of a product is 1.4 by sampling. Naturally cooling the system to 90 ℃, and discharging. Cooled to room temperature and the product was a pale yellow solid.
Comparative example 3
The preparation method of the oily thickener comprises the following steps:
100g of polyglycerol (hydroxyl value 950), 160g of oleic acid and 160g of 12-hydroxystearic acid are added into a 1L reaction kettle, then 0.5g of p-toluenesulfonic acid is added as a catalyst, the temperature is raised to 175 ℃ for reaction, the pressure is-0.075 Mpa, after 3 hours of reaction, after 2 hours of reaction, the reaction system is in a homogeneous transparent state, and the acid value of a product is 1.8 by sampling. Naturally cooling the system to 90 ℃, and discharging. Cool to room temperature and the product is a viscous liquid.
Experimental example:
performance testing
Evaluation of solubility
The thickeners of examples 1 to 8 and comparative examples 1 to 3 were added to various oils, dissolved at 80 ℃ with stirring, and cooled to room temperature to obtain samples. The transparency of the sample was visually observed, and the obtained results are shown in table 1. Preparing concentration: the mass of the thickening agent is 2 percent of that of the oil phase.
A: are readily soluble and compatible.
B: dissolve slowly but are compatible.
C: there was a small amount of precipitation.
D: the precipitation is more.
E: this is not at all the case.
Evaluation of thickening Property
The thickener was added to each oil phase, dissolved at 80 ℃ with stirring, and then cooled to room temperature to prepare a sample. The thickening evaluation was carried out using dynamic viscosity at 25 ℃ under 1 atmosphere. The results are shown in Table 1. Here, the mass of the thickener is 5% of the mass of the oil phase.
A is less than 10000 mPa.s
B: between 10000 mPas and 50000 mPas
C: between 50000 mPas and 80000 mPas
D: between 50000 mPas and 80000 mPas
E: greater than 100000mPa s
Evaluation of transparency
The thickener was added to each oil phase, dissolved at 80 ℃ with stirring, and then cooled to room temperature to prepare a sample. The thickening evaluation was carried out using dynamic viscosity at 25 ℃ under 1 atmosphere. The results are shown in Table 1. Here, the mass of the thickener is 5% of the mass of the oil phase.
A: the transparency is good.
B: exhibit good transparency.
C: slightly cloudy.
D: some of which are cloudy.
E: is completely white and turbid.
The example products were added at 5% to mineral oil (paraffin oil), ester oil (caprylocaprate) and the thickener performance was evaluated in three dimensions of paste forming time, transparency and transparency.
TABLE 1
Figure BDA0003221226240000071
Experiments show that the thickener can achieve ideal effects in three dimensions of compatibility, thickening property and transparency as long as the ratio of the polyglycerol to the long-chain fatty acid variety to the 12-hydroxystearic acid is within a specified range.

Claims (10)

1. A preparation method of an oily thickener comprises the following steps:
mixing polyglycerol with hydroxyl value of 800-1000 with long-chain fatty acid and 12-hydroxystearic acid, reacting under vacuum condition until the acid value is less than 2, and cooling to room temperature for molding to obtain the finished product.
2. The method as set forth in claim 1, wherein the hydroxyl value of the polyglycerol is 850-950.
3. The process according to claim 1, wherein the long-chain fatty acid is stearic acid and/or behenic acid.
4. The process according to claim 1, wherein the long-chain fatty acid is a mixture of stearic acid and behenic acid, and the stearic acid is a stearic acid having a purity of greater than 65% in the mixture, and further wherein the stearic acid is a stearic acid having a purity of greater than 90%, and the mass ratio of stearic acid to behenic acid is 1-2: 2-1.
5. The method according to claim 1, wherein the ratio of the mass of the polyglycerin to the total mass of the long chain fatty acid and the 12-hydroxystearic acid is 100: 300-450; preferably, the ratio of the mass of the polyglycerol to the total mass of the long chain fatty acid and the 12-hydroxystearic acid is 150: 350-420.
6. The production method according to claim 1, wherein the mass ratio of the long-chain fatty acid to the 12-hydroxystearic acid is 3:2 to 1: 3; preferably, the mass ratio of the long-chain fatty acid to the 12-hydroxystearic acid is 1:1-1: 2.
7. The method as claimed in claim 1, wherein the vacuum reaction pressure is from-0.08 to-0.04 MPa and the vacuum reaction temperature is from 180 ℃ to 220 ℃.
8. The preparation method of claim 1, wherein the esterification catalyst is added for reaction during vacuum reaction, when the system is in a homogeneous state, sampling and detecting are carried out, when the acid value is less than 2, the reaction is stopped, the reaction system is naturally cooled to below 90 ℃, and materials are discharged; the esterification catalyst is p-toluenesulfonic acid, potassium hydroxide or butyl titanate.
9. An oily thickener prepared by the method of claim 1.
10. Use of the oily thickener prepared according to claim 1 as a thickener added to the oil phase of a cosmetic, wherein when the thickener is added in an amount of 4-6% by mass of the oil phase, the oil phase forms a gel state at room temperature; the cosmetic oil phase is paraffin oil, olive oil or glyceryl caprylic capric acid ester.
CN202110958515.2A 2021-08-20 2021-08-20 Preparation method and application of oily thickener Pending CN113527662A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001069912A (en) * 1999-08-31 2001-03-21 Mitsubishi-Kagaku Foods Corp Thickener for oil and fat, and thickened oil and fat composition
CN104177649A (en) * 2014-08-06 2014-12-03 河南正通化工有限公司 Polyglycerol fatty acid ester plasticizer and preparation method thereof
JP2016074637A (en) * 2014-10-08 2016-05-12 クラシエホームプロダクツ株式会社 Oily liquid skin detergent composition
CN109628232A (en) * 2019-01-09 2019-04-16 广州美晨科技实业有限公司 A kind of preparation method of polyglyceryl fatty acid ester
JP6825066B1 (en) * 2019-10-30 2021-02-03 太陽化学株式会社 Oil thickener or solidifying agent

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001069912A (en) * 1999-08-31 2001-03-21 Mitsubishi-Kagaku Foods Corp Thickener for oil and fat, and thickened oil and fat composition
CN104177649A (en) * 2014-08-06 2014-12-03 河南正通化工有限公司 Polyglycerol fatty acid ester plasticizer and preparation method thereof
JP2016074637A (en) * 2014-10-08 2016-05-12 クラシエホームプロダクツ株式会社 Oily liquid skin detergent composition
CN109628232A (en) * 2019-01-09 2019-04-16 广州美晨科技实业有限公司 A kind of preparation method of polyglyceryl fatty acid ester
JP6825066B1 (en) * 2019-10-30 2021-02-03 太陽化学株式会社 Oil thickener or solidifying agent

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