Isocaprylic acid isononanoic acid triglyceride and application thereof

Abstract

The invention belongs to the technical field of refrigerating machine oil, and particularly relates to isocaprylic acid and isononanoic acid triglyceride and application thereof. The isocaprylic acid and isononanoic acid triglyceride comprises the following raw materials: isocaprylic acid, isononanoic acid, glycerol, an adsorbent and a catalyst, wherein the molar ratio of the isocaprylic acid to the isononanoic acid is 6: (9-14). By adjusting the ratio of isocaprylic acid to isononanoic acid in the raw materials of the isocaprylic-isononanoic triglyceride, the lubricating property of the isocaprylic-isononanoic triglyceride obtained by the reaction is improved, so that the lubricating property, glossiness and air permeability of the isocaprylic-isononanoic triglyceride are similar to or even slightly superior to those of caprylic-capric triglyceride when the isocaprylic-isononanoic triglyceride is used for cream cosmetics.

Description

Technical Field

[0001] This invention belongs to the field of fine chemical technology, specifically relating to isooctanoic acid isononanoic acid triglyceride and its applications. Background Technology

[0002] Among triglycerides, caprylic / capric triglyceride (GTCC) is a high-quality, odorless oil commonly used as a moisturizing factor base in cosmetics. However, in the industrial production of GTCC, acidic catalysts such as sulfuric acid and p-toluenesulfonic acid are often used for heating and esterification reactions, leading to problems such as yellowing of the crude product and difficulties in refining, resulting in higher costs. Furthermore, the raw material for GTCC, a mixture of caprylic and capric acids, is usually derived from fractions of natural products such as coconut oil or palm kernel oil. This results in the presence of small amounts of unsaturated carboxylic acids in the raw material, which also contributes to the yellowing of the product and affects its quality depending on the batch of raw materials.

[0003] Currently, the selectivity of triglycerides in cosmetics is still relatively small. When the applicant's researchers try to produce other triglycerides, such as tripalmitate, the performance of these triglycerides, which affects cosmetics, is slightly lower than that of caprylic / capric triglyceride.

[0004] Therefore, this paper proposes a triglyceride of isooctanoic acid and its application. Based on optimizing the yellowing problem of its crude product, the lubrication performance and gloss of triglyceride of isooctanoic acid and isononanoic acid in cream cosmetics are similar to or even slightly better than those of triglyceride of caprylic acid and capric acid, thus broadening the variety of triglycerides in cosmetics. Summary of the Invention

[0005] The present invention aims to solve at least one of the technical problems existing in the prior art. To this end, the present invention proposes an isoctanoic acid isononanoic acid triglyceride and its application; based on optimizing the yellowing problem of its crude product, the present invention further makes the lubricating and breathable properties of isoctanoic acid isononanoic acid triglyceride in cream cosmetics similar to or even slightly better than those of caprylic acid capric acid triglyceride, thus broadening the variety of triglycerides in cosmetics.

[0006] The inventive concept of this invention is to improve the lubricating properties of the isooctanoic acid and isononanoic acid in the isooctanoic acid isononanoic acid triglyceride raw material by adjusting the ratio between isooctanoic acid and isononanoic acid.

[0007] The first aspect of the present invention provides isooctanoic acid triglyceride and its application.

[0008] Specifically, an isooctanoic acid isononanoic acid triglyceride, wherein the raw materials of the isooctanoic acid isononanoic acid, glycerol, adsorbent, and catalyst are included, and the molar ratio of isooctanoic acid to isononanoic acid is 6:(9-14).

[0009] Compared with the prior art, the beneficial effects of the isooctanoic acid isononanoic acid triglyceride provided by the first aspect are as follows: by adjusting the ratio between isooctanoic acid and isononanoic acid in the isooctanoic acid isononanoic acid triglyceride raw material, the lubricating properties of the isooctanoic acid isononanoic acid triglyceride obtained by the reaction are improved, so that the lubricating properties, gloss and breathability of isooctanoic acid isononanoic acid triglyceride when used in cream cosmetics are similar to or even slightly better than caprylic acid caprylic acid triglyceride.

[0010] Preferably, the ratio of the sum of the amounts of isooctanoic acid and isononanoic acid to the amount of glycerol is (3.2-3.8):1.

[0011] Preferably, the isooctanoic acid includes 2-ethylhexanoic acid, and the isononanoic acid includes 3,5,5-trimethylhexanoic acid.

[0012] Preferably, the method for preparing the isooctanoic acid isononanoic acid triglyceride includes the following steps: (1) The isooctanoic acid, the isononanoic acid, the glycerol, the adsorbent, and the catalyst are added to a reaction vessel and stirred to mix. (2) Under nitrogen atmosphere and reflux conditions, the temperature is raised to 160-180℃ and reacted for 1-2 hours; (3) Heat to 230-250℃ and react for 2-3 hours to obtain crude product; (4) The crude product is subjected to vacuum distillation, first filtration, alkali washing, water washing, second filtration and dehydration to obtain isooctanoic acid isononanoic acid triglyceride.

[0013] Preferably, in step (1), the adsorbent includes activated carbon, and the amount of activated carbon added is 0.5-1.5 wt% of the sum of the masses of isooctanoic acid, isononanoic acid and glycerol.

[0014] Preferably, in step (1), the catalyst includes sodium bisulfate, and the amount of catalyst added is 0.15-0.25 wt% of the sum of the masses of isooctanoic acid, isononanoic acid and glycerol.

[0015] Preferably, in step (1), the reaction vessel includes a reaction vessel.

[0016] Preferably, in step (1), the temperature of the input is 10-30℃.

[0017] Preferably, in step (1), the mixing time is 0.5-3 hours.

[0018] Preferably, the vacuum distillation includes the following steps: evacuating to -0.09 MPa to -0.1 MPa at 170-190°C for 2-6 hours under a nitrogen atmosphere, followed by natural cooling and replenishment of nitrogen to atmospheric pressure.

[0019] Preferably, the first filtration includes the following steps: filtration at 35-90°C to obtain the liquid phase.

[0020] Preferably, the alkaline washing includes the following steps: adding a 5-15wt% NaOH solution equivalent to 5-15wt% of the crude product at 60-90℃, stirring for 1-2 hours, allowing it to stand and separate into layers to obtain the organic phase; the alkaline washing is performed 1-3 times.

[0021] Preferably, the water washing includes the following steps: adding water equivalent to 15-25 wt% of the crude product at 60-95°C, stirring for 1-2 hours, allowing it to stand and separate into layers to obtain the organic phase; the water washing is performed 1-3 times.

[0022] Preferably, the second filtration includes the following steps: filtration at 35-90°C to obtain the liquid phase.

[0023] Preferably, the dehydration includes the following steps: evacuating to -0.09 MPa to -0.1 MPa at 85-95°C under a nitrogen atmosphere for 2-6 hours, followed by natural cooling and replenishment of nitrogen to atmospheric pressure.

[0024] Preferably, the isooctanoic acid isononanoic acid triglyceride has an acid value ≤0.1mgKOH / g, a color ≤50APHA, an ester content ≥95wt%, a moisture content ≤1000ppm, and is odorless; more preferably, the isooctanoic acid isononanoic acid triglyceride has an acid value of 0.005-0.1mgKOH / g, a color of 10-50APHA, an ester content of 95-99wt%, a moisture content of 10-1000ppm, and is odorless.

[0025] A second aspect of the present invention provides a cream comprising any of the above-mentioned isooctanoic acid isononanoic acid triglycerides.

[0026] Preferably, the cream further includes shea butter, cetearyl alcohol, emulsifier A165, emulsifier 202, rose hydrosol, phenoxyethanol, and water.

[0027] Compared with the prior art, the beneficial effects of the present invention are as follows: (1) By adjusting the ratio between isooctanoic acid and isononanoic acid in the raw material of isooctanoic acid isononanoic acid triglyceride, the lubricating properties of the obtained isooctanoic acid isononanoic acid triglyceride are improved, so that the lubricating properties, gloss and breathability of isooctanoic acid isononanoic acid triglyceride when used in cream cosmetics are similar to or even slightly better than caprylic acid and capric acid triglyceride. (2) In the production process of isooctanoic acid isononanoic acid triglyceride, the crude product is colorless, clear and transparent after simple vacuum distillation, filtration, alkaline washing and water washing, with few impurities, which makes the refining cost less than that of producing caprylic acid and capric acid triglyceride. Attached Figure Description

[0028] Figure 1 The liquid phase spectrum of the crude product after alkali washing in Example 1 is shown below. Figure 2 The infrared spectrum is that of isooctanoic acid isononanoic acid triglyceride prepared in Example 1. Detailed Implementation

[0029] To enable those skilled in the art to more clearly understand the technical solutions described in this invention, the following embodiments are provided for illustration. It should be noted that the following embodiments do not constitute a limitation on the scope of protection claimed by this invention.

[0030] Unless otherwise specified, the raw materials, reagents or devices used in the following examples are available from conventional commercial sources or can be obtained by existing known methods.

[0031] In the embodiments and comparative examples of this invention, shea butter was purchased from Vantage, cetearyl alcohol was purchased from SEPPIC, emulsifier A165 was purchased from SEPPIC, emulsifier 202 was purchased from SEPPIC, and rose hydrosol was purchased from Sichuan Jinshan Rose Technology Co., Ltd.

[0032] The lubrication performance test method of the cream in each embodiment and comparative example of the present invention is as follows: The static friction coefficient and dynamic friction coefficient of the steel slider with different thicknesses of cream on the bottom surface were tested on the leather after 5 minutes using a friction coefficient meter.

[0033] The gloss test method for the cream in the various embodiments and comparative examples of this invention is as follows: The gloss value of the leather surface coated with cream of different thicknesses is measured using a gloss meter (GL200) at a measurement angle of 60°. The initial gloss of the leather is 5.23±0.05.

[0034] The ingredients of the cream in the various embodiments and comparative examples of this invention are as follows: 40g triglycerides, 30g shea butter, 5g cetearyl alcohol, 5g emulsifier A165, 5g emulsifier 202, 100g water, 10g rose hydrosol, and 1g phenoxyethanol.

[0035] The preparation steps of the creams in the various embodiments and comparative examples of the present invention are as follows: (1) Triglycerides, shea butter, cetearyl alcohol, emulsifier A165 and emulsifier 202 were added to a stirring vessel and stirred at 80°C and 600 rpm for 15 min to obtain sample A; (2) Transfer sample A to a homogenizer, add water dropwise to sample A, emulsify at 75℃ and 3000rpm for 3min to obtain sample B; (3) Transfer sample B to a mixing vessel, add rose hydrosol and phenoxyethanol, stir at 45°C and 300 rpm for 15 min to obtain the cream. Example 1

[0036] The isooctanoic acid-isononanoic acid triglyceride is prepared by the following steps: The molar ratio of 2-ethylhexanoic acid to 3,5,5-trimethylhexanoic acid in the raw materials is 3:7. (1) 144.5g of 2-ethylhexanoic acid (1.08mol, 155.75g), 2,5,5-trimethylhexanoic acid (2.52mol, 398.76g), glycerol (1mol, 92.09g), activated carbon adsorbent (1wt%, 6.47g), and sodium bisulfate catalyst (0.2wt%, 1.29g) were added to the reactor at a controlled temperature of 25°C and stirred for 1 hour. (2) The temperature was raised to 170℃ and reacted for 1.5 h under nitrogen atmosphere and reflux conditions; (3) Continue heating to 240℃ and react for 2.5 h to obtain crude product; (4) Crude product processing: Vacuum distillation: Under a nitrogen atmosphere, distill at 180℃ until a vacuum of -0.095 MPa is applied for 3 hours. After completion, allow the mixture to cool naturally and replenish with nitrogen to atmospheric pressure. First filtration: Cool to 85℃, filter and collect the liquid phase. Alkali washing: Add a 10wt% NaOH solution (equivalent to 10wt% of the crude product) at 85℃, stir for 1.5 hours, allow to stand and separate into layers, and take the organic phase. The alkali washing is performed twice. Water washing: Add water equivalent to 20wt% of the crude product at 85℃, stir for 1.5h, allow to stand and separate into layers, and collect the organic phase; the washing process is repeated 3 times. Second filtration: Filter and collect the liquid phase at 85℃. Dehydration: Under a nitrogen atmosphere, the pressure was evacuated to -0.095 MPa for 4 hours at 90°C, then allowed to cool naturally and nitrogen was added to bring the pressure to atmospheric pressure to obtain isooctanoic acid isononanoic acid triglyceride.

[0037] The crude product after alkali washing and water washing is transparent and colorless.

[0038] Figure 1 The liquid phase spectrum of the crude product after alkali washing shows that the isooctanoic acid isononanoic acid triglyceride prepared by this method has fewer impurity peaks and fewer side reactions. The finished product can be obtained by simple alkali washing and water washing, which greatly reduces the production cost.

[0039] Figure 2 The infrared spectrum is that of isooctanoic acid isononanoic acid triglyceride prepared in Example 1.

[0040] The isooctanoic acid triglyceride prepared in Example 1 has an acid value of 0.01 mg KOH / g, a color of 30 APHA, an ester content of 97 wt%, a moisture content of 50 ppm, and no odor.

[0041] The isooctanoic acid triglyceride obtained in Example 1 was prepared into a cream, and its lubrication performance, breathability and gloss were tested at different application thicknesses. The results are recorded in Table 1.

[0042] Comparative Example 1 The difference between Comparative Example 1 and Example 1 is that the molar ratio of 2-ethylhexanoic acid and 3,5,5-trimethylhexanoic acid is 1:1 (1.8 mol: 1.8 mol), the amount of other raw materials remains unchanged, and the mass percentage of catalyst adsorbent added remains unchanged.

[0043] The isooctanoic acid triglyceride prepared in Comparative Example 1 had an acid value of 0.01 mg KOH / g, a color of 40 APHA, an ester content of 96 wt%, a moisture content of 80 ppm, and no odor.

[0044] The isooctanoic acid-isononanoic acid triglyceride obtained in Comparative Example 1 was prepared into a cream, and its lubrication performance, breathability, and gloss were tested at different application thicknesses. The results are recorded in Table 1.

[0045] Comparative Example 2 The difference between Comparative Example 2 and Example 1 is that the molar ratio of 2-ethylhexanoic acid and 3,5,5-trimethylhexanoic acid is 7:3 (2.52 mol: 1.08 mol), while the amount of other raw materials and the mass percentage of catalyst adsorbent added remain unchanged.

[0046] The isooctanoic acid triglyceride prepared in Comparative Example 2 had an acid value of 0.01 mg KOH / g, a color of 30 APHA, an ester content of 95 wt%, a moisture content of 60 ppm, and no odor.

[0047] The isooctanoic acid-isononanoic acid triglyceride obtained in Comparative Example 1 was prepared into a cream, and its lubrication performance, breathability, and gloss were tested at different application thicknesses. The results are recorded in Table 1.

[0048] Comparative Example 3 Comparative Example 3 was caprylic / capric triglyceride (CAS: 65381-09-1) purchased from SEPPIC. The raw material had a molar ratio of caprylic acid to capric acid of 58:42; an acid value of 0.01 mg KOH / g; a color of 40 APHA; an ester content of 96 wt%; a moisture content of 90 ppm; and no odor.

[0049] The caprylic / capric triglyceride of Comparative Example 3 was prepared into a cream, and its lubrication, breathability and gloss were tested at different application thicknesses. The results are recorded in Table 1.

[0050] Table 1. Lubrication properties, breathability, and gloss of the creams in Examples 1 and Comparative Examples 1-3.

[0051] Spread thickness Example 1 Comparative Example 1 Comparative Example 2 Comparative Example 3 10 μm Static friction coefficient 0.241 0.263 0.268 0.243 10 μm Dynamic friction coefficient 0.184 0.211 0.206 0.178 10 μm Gloss 7.76 7.02 7.23 7.41 40 μm Static friction coefficient 0.138 0.156 0.159 0.137 40 μm Dynamic friction coefficient 0.102 0.135 0.127 0.115 40 μm Gloss 8.97 8.73 8.81 9.13 By adjusting the ratio of isooctanoic acid and isononanoic acid in the raw material of isooctanoic acid isononanoic acid triglyceride, the lubricating properties of the resulting isooctanoic acid isononanoic acid triglyceride are improved, so that the lubricating properties, gloss and breathability of isooctanoic acid isononanoic acid triglyceride when used in cream cosmetics are similar to or even slightly better than caprylic acid caprylic acid triglyceride.

Claims

1. A triglyceride of isooctanoic acid and isononanoic acid, characterized in that, The raw materials for the isooctanoic acid-isononanoic acid triglyceride include isooctanoic acid, isononanoic acid, glycerol, adsorbent, and catalyst, and the molar ratio of isooctanoic acid to isononanoic acid is 6:(9-14).

2. The isooctanoic acid isononanoic acid triglyceride according to claim 1, characterized in that, The ratio of the sum of the amounts of isooctanoic acid and isononanoic acid to the amount of glycerol is (3.2-3.8):

1.

3. The isooctanoic acid isononanoic acid triglyceride according to claim 1, characterized in that, The isooctanoic acid includes 2-ethylhexanoic acid, and the isononanoic acid includes 3,5,5-trimethylhexanoic acid.

4. The isooctanoic acid isononanoic acid triglyceride according to claim 1, characterized in that, The method for preparing the isooctanoic acid isononanoic acid triglyceride includes the following steps: (1) The isooctanoic acid, the isononanoic acid, the glycerol, the adsorbent, and the catalyst are added to a reaction vessel and stirred to mix. (2) Under nitrogen atmosphere and reflux conditions, the temperature is raised to 160-180℃ and reacted for 1-2 hours; (3) Heat to 230-250℃ and react for 2-3 hours to obtain crude product; (4) The crude product is subjected to vacuum distillation, first filtration, alkali washing, water washing, second filtration and dehydration to obtain isooctanoic acid isononanoic acid triglyceride.

5. The isooctanoic acid isononanoic acid triglyceride according to claim 4, characterized in that, In step (1), the adsorbent includes activated carbon, and the amount of activated carbon added is 0.5-1.5 wt% of the sum of the masses of isooctanoic acid, isononanoic acid and glycerol.

6. The isooctanoic acid isononanoic acid triglyceride according to claim 4, characterized in that, In step (1), the catalyst includes sodium bisulfate, and the amount of catalyst added is 0.15-0.25 wt% of the sum of the masses of isooctanoic acid, isononanoic acid and glycerol.

7. The isooctanoic acid isononanoic acid triglyceride according to claim 4, characterized in that, The alkaline washing includes the following steps: adding a 5-15wt% NaOH solution equivalent to 5-15wt% of the crude product at 60-90℃, stirring for 1-2 hours, allowing it to stand and separate into layers, and taking the organic phase; the alkaline washing is performed 1-3 times.

8. The isooctanoic acid isononanoic acid triglyceride according to claim 1, characterized in that, The isooctanoic acid triglyceride has an acid value ≤0.1mgKOH / g, a color ≤50APHA, an ester content ≥95wt%, a moisture content ≤1000ppm, and is odorless.

9. A second aspect of the present invention provides a cream comprising any of the above-described isooctanoic acid isononanoic acid triglycerides.

10. Preferably, the cream further includes shea butter, cetearyl alcohol, emulsifier A165, emulsifier 202, rose hydrosol, phenoxyethanol, and water.

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