Composition as well as preparation method, application and daily chemical product thereof

Abstract

The invention discloses a composition and a preparation method and application thereof and a daily chemical product, the composition comprises a compound A and a compound B. The chemical formula of the compound A is R-COO-CH (CH3) CH2-SO3X, the chemical formula of the compound B is R-COO-CH2CH (CH3)-SO3X, R is alkyl with the carbon atom number of 5-23, and S is alkyl with the carbon atom number of 5-23. X comprises hydrogen atoms, alkali metal ions, alkaline earth metal ions, aluminum ions, zinc ions or ammonium radicals, and the molar ratio of the compound A to the compound B is (90.5-93.5): (6.5-9.5). The composition can inhibit 5alpha-reductase, so that the composition is applied to daily chemical products, and the daily chemical products have oil control and hair loss prevention effects at the same time.

Description

Technical Field

[0001] The present invention belongs to the field of daily chemical products, and in particular relates to a composition, a preparation method thereof, uses thereof, and daily chemical products. Background Art

[0002] Human 5α-reductase is known to have two isoenzymes, type 1 and type 2. Type 1 is present in the liver, lungs, and non-genital skin and appendages, while type 2 is primarily found in the prostate, seminal vesicles, and inner hair root sheaths. These isoenzymes are encoded by SRD5A1 and SRD5A2, respectively. Both genes consist of five exons and four introns. SRD5A1 is located on chromosome 5p15, and SRD5A2 is located on chromosome 2p23. Type 1 and type 2 share approximately 50% amino acid identity. Type 2 has a greater affinity than type 1 for substrates such as testosterone and the 5α-reductase type 2 inhibitor finasteride. Current research suggests that type 1 is most closely associated with oil secretion, while type 2 is most closely associated with male pattern baldness.

[0003] Therefore, daily chemical products that inhibit 5α-reductase need to be studied. Summary of the Invention

[0004] The present invention aims to address at least one of the above-mentioned technical problems to a certain extent. To this end, one object of the present invention is to provide a composition, a preparation method, uses thereof, and a daily chemical product. The composition can inhibit 5α-reductase, thereby enabling its application in daily chemical products to achieve both oil control and hair loss prevention effects.

[0005] The first aspect of the present invention provides a composition comprising compound A and compound B.

[0006] The chemical formula of compound A is R-COO-CH(CH3)CH2-SO3X, the chemical formula of compound B is R-COO-CH2CH(CH3)-SO3X, R is a hydrocarbon group with 5-23 carbon atoms, X includes a hydrogen atom, an alkali metal ion, an alkaline earth metal ion, an aluminum ion, a zinc ion or an ammonium ion, and the molar ratio of compound A to compound B is (90.5-93.5):(6.5-9.5).

[0007] Therefore, by controlling the molar ratio of compound A and compound B to (90.5-93.5): (6.5-9.5), the composition can inhibit 5α-reductase, and thus be applied to daily chemical products, so that the daily chemical products have both oil control and anti-hair loss effects.

[0008] In some embodiments of the present invention, R comprises an alkyl group having 5 to 17 carbon atoms, thereby improving the 5α-reductase inhibitory effect of the composition.

[0009] In some embodiments of the present invention, the compound A comprises at least one of the following: CH3CH2CH2 (CH2CH2) 3- 4CH2CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2)9CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2) 15 CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2) 16 CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2) 21 CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2)3CH2-COO-CH(CH3)CH2-SO3X. This can enhance the 5α-reductase inhibitory effect of the composition.

[0010] In some embodiments of the present invention, the compound B comprises at least one of the following: CH3CH2CH2(CH2CH2) 3- 4CH2CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2) 11 CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2)9CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2) 15 CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2) 16 CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2) 21 CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2)3CH2-COO-CH2CH(CH3)-SO3X. This can enhance the 5α-reductase inhibitory effect of the composition.

[0011] In some embodiments of the present invention, the total weight of compound A and compound B accounts for no less than 80%, preferably 80%-93%, of the total weight of the composition, thereby improving the 5α-reductase inhibitory effect of the composition.

[0012] In some embodiments of the present invention, at least one of the following conditions is met:

[0013] Based on the total mass of the composition, the mass proportion of fatty acids is no more than 7%;

[0014] Based on the total mass of the composition, the total mass of HO-CH(CH3)CH2-SO3X and HO-CH2CH(CH3)-SO3X accounts for no more than 7%;

[0015] Based on the total mass of the composition, the mass proportion of water is no more than 1%.

[0016] This can enhance the 5α-reductase inhibitory effect of the composition.

[0017] A second aspect of the present invention provides a method for preparing the above-mentioned composition, comprising:

[0018] (1) subjecting HSO3X and propylene oxide to a ring-opening reaction to obtain a mixture comprising HO-CH(CH3)CH2-SO3X and HO-CH2CH(CH3)-SO3X;

[0019] (2) adjusting the molar ratio of HO-CH(CH3)CH2-SO3X and HO-CH2CH(CH3)-SO3X in the mixture to (90.5-93.5):(6.5-9.5);

[0020] (3) reacting the adjusted mixture obtained in step (2) with a fatty acid in the presence of a catalyst to obtain a composition comprising compound A and compound B.

[0021] Thus, the method of the present invention can be used to obtain the composition of the above composition, which can inhibit 5α-reductase, and thus be applied to daily chemical products, so that the daily chemical products have both oil control and anti-hair loss effects.

[0022] In some embodiments of the present invention, in step (1), the ring-opening reaction satisfies one or more of the following:

[0023] The ring-opening reaction temperature is 35°C-75°C;

[0024] The ring-opening reaction time is 0.5 hours to 1 hour;

[0025] The ring-opening reaction pressure is 0-0.04 MPa;

[0026] The initial pH of the ring-opening reaction is 5.6-6.6;

[0027] The molar ratio of the bisulfite to propylene oxide is 1:(1-1.05).

[0028] Thereby, the yield of methyl isethionate can be increased.

[0029] In some embodiments of the present invention, step (2) is performed according to the following steps: supplying the mixture to a chromatographic column for isocratic elution, using ethanol as mobile phase A and water as mobile phase B.

[0030] In some embodiments of the present invention, the volume ratio of the mobile phase A to the mobile phase B is (12-24): (88-76).

[0031] In some embodiments of the present invention, in step (3), the fatty acid includes a fatty acid having 6-24 carbon atoms.

[0032] In some embodiments of the present invention, the fatty acid comprises at least one of caproic acid, caprylic acid, capric acid, coconut acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, erucic acid and lignoceric acid.

[0033] In some embodiments of the present invention, the molar ratio of the adjusted mixture to the fatty acid is 1:(0.9-1.1). Thus, the yield of compound A and compound B can be increased.

[0034] In some embodiments of the present invention, in step (3), the catalyst includes at least one of p-toluenesulfonic acid, p-toluenesulfonate, methylisothionate, methylisothionate, phosphorous acid, phosphite, sulfuric acid, sulfate, citric acid, citrate, zirconium oxide, magnesium oxide, zinc oxide and aluminum oxide.

[0035] In some embodiments of the present invention, based on the total mass of the fatty acid and the adjusted mixture, the added mass of the catalyst accounts for 0.2%-0.9%.

[0036] In some embodiments of the present invention, the reaction temperature is 205°C-235°C.

[0037] In some embodiments of the present invention, the reaction time is 6.5 hours to 8.5 hours.

[0038] In some embodiments of the present invention, the reaction pressure is 0-0.05 MPa.

[0039] In some embodiments of the present invention, the method further comprises: performing reduced pressure distillation on the system while the adjusted mixture reacts with fatty acids in the presence of a catalyst. This can reduce the fatty acid content in the composition and enhance the 5α-reductase inhibitory effect of the composition.

[0040] In some embodiments of the present invention, the temperature of the reduced pressure distillation is 205°C-235°C.

[0041] In some embodiments of the present invention, the time of the reduced pressure distillation is 4 hours to 8 hours.

[0042] In some embodiments of the present invention, the pressure of the reduced pressure distillation is -0.04 MPa to -0.09 MPa.

[0043] The third aspect of the present invention provides the use of the above-mentioned composition or the composition obtained by the above-mentioned method in inhibiting 5α-reductase.

[0044] The fourth aspect of the present invention provides the use of the above-mentioned composition or the composition obtained by the above-mentioned method in the field of preparing daily chemical products.

[0045] In some embodiments of the present invention, the daily chemical product is used to inhibit 5α-reductase.

[0046] In some embodiments of the present invention, the daily chemical product is used for preventing hair loss and controlling oil.

[0047] In a fifth aspect, the present invention provides a daily chemical product comprising the above-mentioned composition or the composition obtained by the above-mentioned method. Thus, the daily chemical product has both oil control and hair loss prevention effects.

[0048] Additional aspects and advantages of the present invention will be set forth in part in the description which follows and, in part, will be obvious from the description which follows, or may be learned by practice of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS

[0049] The above and / or additional aspects and advantages of the present invention will become apparent and readily understood from the description of the embodiments with reference to the following drawings, in which:

[0050] Figure 1 is a schematic flow chart of a method for preparing a composition according to one embodiment of the present invention;

[0051] Figure 2 is the NMR spectrum of the product obtained in step (1) of Example 1;

[0052] Figure 3 is the NMR spectrum of the composition obtained in Example 1;

[0053] Figure 4 is the NMR spectrum of the product obtained in step (1) of Example 2;

[0054] Figure 5 is the NMR spectrum of the composition obtained in Example 2;

[0055] Figure 6 is the NMR spectrum of the product obtained in step (1) of Example 3;

[0056] Figure 7 is the NMR spectrum of the composition obtained in Example 3;

[0057] Figure 8is the NMR spectrum of the product obtained in step (1) of Example 4;

[0058] Figure 9 is the NMR spectrum of the composition obtained in Example 4;

[0059] Figure 10 is the NMR spectrum of the composition obtained in Example 5;

[0060] Figure 11 is the NMR spectrum of the composition obtained in Example 6;

[0061] Figure 12 is the NMR spectrum of the composition obtained in Example 7;

[0062] Figure 13 This is the NMR spectrum of the product obtained in step (1) of Comparative Example 1;

[0063] Figure 14 This is the NMR spectrum of the composition obtained in Comparative Example 1;

[0064] Figure 15 This is the NMR spectrum of the product obtained in step (1) of Comparative Example 2;

[0065] Figure 16 This is the NMR spectrum of the composition obtained in Comparative Example 2;

[0066] Figure 17 This is the NMR spectrum of the product obtained in step (1) of Comparative Example 3;

[0067] Figure 18 This is the NMR spectrum of the composition obtained in Comparative Example 3;

[0068] Figure 19 This is the NMR spectrum of the product obtained in step (1) of Comparative Example 4;

[0069] Figure 20 This is the NMR spectrum of the composition obtained in Comparative Example 4;

[0070] Figure 21 This is the NMR spectrum of the product obtained in step (1) of Comparative Example 5;

[0071] Figure 22 This is the NMR spectrum of the composition obtained in Comparative Example 5;

[0072] Figure 23 This is the NMR spectrum of the product obtained in step (1) of Comparative Example 6;

[0073] Figure 24 This is the NMR spectrum of the composition obtained in Comparative Example 6;

[0074] Figure 25 This is the NMR spectrum of the product obtained in step (1) of Comparative Example 7;

[0075] Figure 26 This is the NMR spectrum of the composition obtained in Comparative Example 7;

[0076] Figure 27 Spectra of SRD5A1 gene expression rates of the compositions of Examples 1-7 and Comparative Examples 1-7 and a control group;

[0077] Figure 28 Spectra of inhibition rates of the compositions of Examples 1-7 and Comparative Examples 1-7 and the positive group on 5α-reductase type 2;

[0078] Figure 29 The expression rate spectrum of SRD5A1 gene expression of the detergent of Experimental Example 1 configured with the compositions of Examples 1-7 and Comparative Examples 1-7 and the control group;

[0079] Figure 30 This is a graph showing the inhibition rate of the detergent of Experimental Example 1 and the positive group on 5α-reductase type 2, which are configured with the compositions of Examples 1-7 and Comparative Examples 1-7. DETAILED DESCRIPTION

[0080] The embodiments of the present invention are described in detail below, which are intended to explain the present invention but are not to be construed as limiting the present invention.

[0081] In a first aspect, the present invention provides a composition comprising compound A and compound B, wherein the chemical formula of compound A is R-COO-CH(CH3)CH2-SO3X, the chemical formula of compound B is R-COO-CH2CH(CH3)-SO3X, R is a hydrocarbon group having 5 to 23 carbon atoms, X comprises a hydrogen atom, an alkali metal ion, an alkaline earth metal ion, an aluminum ion, a zinc ion or an ammonium ion, and the molar ratio of compound A to compound B is (90.5-93.5):(6.5-9.5).

[0082] The inventors have found that by compounding compound A and compound B, and controlling the molar ratio of compound A and compound B in the composition to be (90.5-93.5): (6.5-9.5), for example (91-93): (6.5-9.5), (91.5-92.5): (6.5-9.5), (92-92.3): (6.5-9.5), (90.5-93.5): (7.5-8.5), (90.5-93.5): (8-8.3), etc., the appropriate ratio of compound A and compound B can ensure that the oil layer of human skin is removed by washing without excessively damaging the stratum corneum of human skin, ensuring that the active ingredients of the present composition reach subcutaneous cells in small amounts. Thus, the composition composed of the present application can inhibit 5α-reductase, thereby being applied to daily chemical products, so that the daily chemical products have both oil control and anti-hair loss effects.

[0083] As an example, alkali metal ions refer to ions corresponding to the six metal elements in Group IA of the periodic table except hydrogen (H), such as lithium ions, sodium ions, potassium ions, rubidium ions, and cesium ions; alkaline earth metal ions refer to ions corresponding to the elements in Group ⅡA of the periodic table, such as beryllium ions, magnesium ions, calcium ions, strontium ions, and barium ions.

[0084] In some embodiments of the present invention, in the chemical formulas of Compound A and Compound B, R comprises an alkyl group with 5-17 carbon atoms. Therefore, Compounds A and B in which R1 comprises an alkyl group with 5-17 carbon atoms have high solubility and are less likely to agglomerate, increasing their contact area with the skin and allowing them to easily pass through the stratum corneum, exerting excellent 5α-reductase inhibition effects. Therefore, they can be fully dispersed in daily chemical products, further enhancing their oil control and hair loss prevention effects.

[0085] As an example, the compound A includes at least one of the following: CH3CH2CH2(CH2CH2) 3-4 CH2CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2)9CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2) 15 CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2) 16 CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2) 21 CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2)3CH2-COO-CH(CH3)CH2-SO3X; the compound B comprises at least one of the following: CH3CH2CH2(CH2CH2) 3-4 CH2CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2) 11 CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2)9CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2) 15 CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2) 16 CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2) 21 CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2)3CH2-COO-CH2CH(CH3)-SO3X.

[0086] In some embodiments of the present invention, based on the total mass of the composition, the total mass of the compound A and the compound B accounts for no less than 80%, for example, 80%-98%, 82%-97%, 85%-96%, 87%-95%, 90%-93%, 91%-92%, etc. Thus, the total mass proportion of compound A and compound B in the control composition of the present application satisfies the above conditions, which can improve the 5α-reductase inhibition effect of the composition, thereby applying it to daily chemical products, so that the daily chemical products have both oil control and anti-hair loss effects. In other embodiments of the present invention, based on the total mass of the composition, the total mass of the compound A and the compound B accounts for 80%-93%. Thus, the 5α-reductase inhibition effect of the composition can be further improved.

[0087] In some embodiments of the present invention, the weight percentage of fatty acids based on the total weight of the composition is no more than 7%. Specifically, when fatty acids are used as raw materials for preparing Compound A and Compound B, controlling the weight percentage of fatty acids in the composition to meet the above conditions can further enhance the 5α-reductase inhibitory effect of the composition, thereby enabling its application in daily chemical products to achieve both oil control and hair loss prevention effects.

[0088] In some embodiments of the present invention, based on the total mass of the composition, the total mass proportion of HO-CH(CH3)CH2-SO3X and HO-CH2CH(CH3)-SO3X is no more than 7%. Specifically, HO-CH(CH3)CH2-SO3X and HO-CH2CH(CH3)-SO3X are intermediate products for preparing compound A and compound B. Controlling the total mass proportion of HO-CH(CH3)CH2-SO3X and HO-CH2CH(CH3)-SO3X in the composition to meet the above conditions can further improve the 5α-reductase inhibition effect of the composition, thereby applying it to daily chemical products, so that the daily chemical products have both oil control and anti-hair loss effects.

[0089] In some embodiments of the present invention, the weight percentage of water based on the total weight of the composition is no more than 1%. Thus, by controlling the water content in the composition to meet the above conditions, the composition's 5α-reductase inhibition effect can be further enhanced, thereby enabling its application in daily chemical products to achieve both oil control and hair loss prevention effects.

[0090] The second aspect of the present invention provides a method for preparing the above composition. Figure 1 , the method comprising:

[0091] S100: Ring-opening reaction of HSO3X and propylene oxide

[0092] In some embodiments of the present invention, HSO3X and propylene oxide are subjected to a ring-opening reaction to obtain a mixture including HO-CH(CH3)CH2-SO3X and HO-CH2CH(CH3)-SO3X.

[0093] Furthermore, the ring-opening reaction temperature is 35°C-75°C, for example, 40°C-70°C, 45°C-65°C, 50°C-60°C, 55°C-60°C, etc.; and / or the ring-opening reaction time is 0.5 hour-1 hour, for example, 0.5 hour, 0.8 hour, 1 hour, etc.; and / or the ring-opening reaction pressure is 0-0.04MPa, for example, 0.01MPa, 0.02MPa, 0.03MPa, 0.04MPa, etc.; and / or the initial pH of the ring-opening reaction is 5.6-6.6, for example, 5.8-6.4, 6-6.2, 6-6.1, etc.; and / or the molar ratio of HSO3X to propylene oxide is 1:(1-1.05), for example, 1:1, 1:1.02, 1:1.03, 1:1.05, etc. Therefore, the present invention controls the reaction conditions of the ring-opening reaction of HSO3X and propylene oxide to meet one or more of the above conditions, which can increase the yield of methyl isethionate.

[0094] S200: Adjust the molar ratio of HO-CH(CH3)CH2-SO3X and HO-CH2CH(CH3)-SO3X in the mixture to (90.5-93.5):(6.5-9.5)

[0095] In some embodiments of the present invention, the molar ratio of HO-CH(CH3)CH2-SO3X and HO-CH2CH(CH3)-SO3X in the mixture can be adjusted by liquid chromatography. For example, the mixture is supplied to a chromatographic column, such as a PFP chromatographic column, for isocratic elution, with ethanol as mobile phase A and water as mobile phase B, and the volume ratio of the mobile phase A to the mobile phase B is (12-24):(88-76), for example, the volume ratio of the mobile phase A to the mobile phase B is 12:88, 15:85, 19:81, or 24:76.

[0096] S300: reacting the adjusted mixture obtained in S200 with fatty acid in the presence of a catalyst

[0097] In some embodiments of the present invention, the adjusted mixture obtained above is reacted with a fatty acid in the presence of a catalyst to obtain a composition comprising compound A and compound B.

[0098] Furthermore, the fatty acid includes a fatty acid with 6-24 carbon atoms, for example, the fatty acid includes at least one of caproic acid, caprylic acid, capric acid, coconut acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, erucic acid and lignoceric acid.

[0099] Furthermore, the molar ratio of the adjusted mixture to the fatty acid is 1:(0.9-1.1), for example 1:0.9, 1:1, 1:1.1, etc. Thus, the present invention controls the adjusted mixture and the fatty acid to be mixed according to the above ratio, which can increase the yield of compound A and compound B.

[0100] As an example, the catalyst includes at least one of p-toluenesulfonic acid, p-toluenesulfonate, methylisothionic acid, methylisothionate, phosphorous acid, phosphite, sulfuric acid, sulfate, citric acid, citrate, zirconium oxide, magnesium oxide, zinc oxide, and aluminum oxide.

[0101] Furthermore, based on the total mass of the fatty acid and the adjusted mixture, the added catalyst accounts for 0.2% to 0.9% by mass, for example, 0.3% to 0.8%, 0.4% to 0.7%, 0.5% to 0.6%, etc. Thus, the present invention controls the amount of catalyst to meet the above conditions, which can significantly increase the reaction rate of the fatty acid and methyl isethionate.

[0102] Furthermore, the reaction temperature is 205°C-235°C, for example, 210°C-230°C, 215°C-225°C, 220°C-223°C, etc.; and / or the reaction time is 6.5 hours-8.5 hours, for example, 6.5 hours, 7 hours, 7.5 hours, 8 hours, 8.5 hours, etc.; and / or the reaction pressure is 0-0.05 MPa, for example, 0.01 MPa, 0.02 MPa, 0.03 MPa, 0.04 MPa, 0.05 MPa, etc. Thus, the reaction conditions of the adjusted mixture and the fatty acid are controlled to meet one or more of the above conditions, thereby improving the yield of compound A and compound B.

[0103] Thus, the method of the present invention can be used to obtain the composition of the above composition, which can inhibit 5α-reductase, and thus be applied to daily chemical products, so that the daily chemical products have both oil control and anti-hair loss effects.

[0104] In some embodiments of the present invention, the method further comprises: while the adjusted mixture reacts with the fatty acid in the presence of a catalyst, performing reduced pressure distillation on the system to remove a portion of unreacted fatty acids.

[0105] Furthermore, the temperature of the vacuum distillation is 205°C-235°C, such as 210°C-230°C, 215°C-225°C, 220°C-223°C, etc.; the time of the vacuum distillation is 4 hours-8 hours, such as 4.5 hours-7.5 hours, 5 hours-7 hours, 5.5 hours-6.5 hours, 5.8 hours-6 hours, etc.; the pressure of the vacuum distillation is -0.04 MPa to -0.09 MPa, such as -0.08 MPa to -0.05 MPa, -0.07 MPa to -0.06 MPa, etc. Thus, the reaction conditions of the vacuum distillation process of the present invention are controlled to meet one or more of the above conditions, which can increase the total proportion of compound A and compound B in the composition, further improve the 5α-reductase inhibition effect of the composition, and thus be applied to daily chemical products, so that the daily chemical products have both oil control and anti-hair loss effects.

[0106] Thus, the method of the present invention can be used to obtain the composition of the above composition, which can inhibit 5α-reductase, and thus be applied to daily chemical products, so that the daily chemical products have both oil control and anti-hair loss effects.

[0107] The third aspect of the present invention provides the use of the above-mentioned composition or the composition obtained by the above-mentioned method in inhibiting 5α-reductase.

[0108] The fourth aspect of the present invention provides the use of the above-mentioned composition or the composition obtained by the above-mentioned method in the field of preparing daily chemical products.

[0109] As an example, the daily chemical products may include detergent, shampoo, shower gel, facial cleanser, hand soap, facial cleansing bath bubbles, etc.

[0110] In some embodiments of the present invention, the daily chemical product is used to inhibit 5α-reductase.

[0111] In some embodiments of the present invention, the daily chemical product is used for preventing hair loss and controlling oil.

[0112] In a fifth aspect, the present invention provides a daily chemical product comprising the above-mentioned composition or the composition obtained by the above-mentioned method. Thus, the daily chemical product has both oil control and hair loss prevention effects.

[0113] In some embodiments of the present invention, the composition accounts for 0.5% to 17.5% of the total mass of the daily chemical product. Thus, the daily chemical product has both oil control and anti-hair loss effects.

[0114] In some embodiments of the present invention, the daily chemical product further comprises at least one of a surfactant, a functional additive and a solvent.

[0115] In some embodiments of the present invention, the surfactant includes at least one of anionic surfactants, amphoteric surfactants, nonionic surfactants and cationic surfactants.

[0116] As an example, the anionic surfactant includes ammonium lauryl sulfate, triethanolamine lauryl polyoxyethylene ether sulfate, monoethanolamine lauryl sulfate, monoethanolamine lauryl polyoxyethylene ether sulfate, diethanolamine lauryl sulfate, diethanolamine lauryl polyoxyethylene ether sulfate, sodium lauric acid monoglyceride sulfate, sodium lauryl sulfate, sodium lauryl polyoxyethylene ether sulfate, fatty acids, potassium lauryl sulfate, ammonium lauryl polyoxyethylene ether sulfate, triethylamine lauryl sulfate, triethylamine lauryl polyoxyethylene ether sulfate, sodium alkylbenzene sulfonate, At least one of ammonium alkylbenzene sulfonate, sodium fatty methyl taurate, triethanolamine lauryl sulfate, potassium lauryl polyoxyethylene ether sulfate, sodium lauryl sarcosinate, sodium lauroyl sarcosinate, lauryl sarcosinate, fatty alcohol glyceryl ether sulfonate, coconut oil sarcosine, ammonium coconut oil sulfate, ammonium lauryl sulfate, sodium coconut oil sulfate, fatty alcohol ether carboxylate, sodium lauroyl sulfate, potassium coconut oil sulfate, potassium lauryl sulfate, triethanolamine lauryl sulfate, triethanolamine lauryl sulfate, monoethanolamine coconut oil sulfate and monoethanolamine lauryl sulfate.

[0117] As an example, the amphoteric surfactants include sodium cocoylaminopropionate, sodium lauryl iminodipropionate, ammonium cocoylaminopropionate, ammonium cocoylaminodipropionate, ammonium cocoamphoacetate, ammonium cocoamphohydroxypropyl sulfonate, ammonium cocoamphopropionate, ammonium corn amphopropionate, ammonium laurylaminopropionate, ammonium lauroamphoacetate, ammonium lauroamphohydroxypropyl sulfonate, sodium cocoylaminodipropionate, sodium cocoamphoacetate, sodium cocoamphohydroxypropyl sulfonate, sodium cocoamphopropionate, sodium corn amphopropionate, sodium laurylaminopropionate, sodium lauroamphoacetate, sodium lauroamphohydroxypropyl sulfonate, Sodium corn amphopropionate, sodium lauroylamphopropionate, ammonium corn amphopropionate, ammonium lauriliminodipropionate, triethanolamine cocoylaminopropionate, triethanolamine cocoylaminodipropionate, triethanolamine cocoylamphoacetate, triethanolamine cocoylamphohydroxypropylsulfonate, triethanolamine cocoylamphopropionate, triethanolamine corn amphopropionate, triethanolamine lauroylaminopropionate, triethanolamine lauroylamphoacetate, triethanolamine lauroylamphohydroxypropylsulfonate, triethanolamine cocoylamphopropionate, triethanolamine corn amphopropionate, triethanolamine lauriliminodipropionate, triethanolamine cocoylamphodipropionic acid, capryloylampho Disodium Diacetate, Disodium Capryloamphodipropionate, Disodium Capryloamphodiacetate, Disodium Capryloamphodipropionate, Disodium Cocoamphocarboxyethyl Hydroxypropyl Sulfonate, Disodium Cocoamphodiacetate, Disodium Cocoamphodipropionate, Disodium Dicarboxyethyl Cocopropylenediamine, Disodium Laureth-5 Carboxyamphodiacetate, Disodium Lauriminodipropionate, Disodium Lauroamphodiacetate, Disodium Lauroamphodipropionate, Disodium Oleylamphodipropionate, PPG-2-Isodecyl Ether-7 Carboxyamphodiacetate, Laurylaminopropionic Acid, Lauroamphodipropionic Acid, Laurylaminopropyl Glycine, Lauryl Diethylenediamine At least one of glycine, sodium cocoamphodiacetate, sodium lauroamphodiacetate, cocamidoethyl betaine, cocamidopropylamine oxide, cocamidopropyl betaine, cocamidopropyl dimethylaminohydroxypropyl hydrolyzed collagen, cocamidopropyl dimonium hydroxypropyl hydrolyzed collagen, cocamidopropyl hydroxysultaine, cocobetaine amidoamphopropionate, cocobetaine, cocohydroxysultaine, coco / oleamidopropyl betaine, cocosulfobetaine, lauramidopropyl betaine, lauryl betaine, lauryl hydroxysultaine, lauryl sultaine and cocosulfobetaine.

[0118] As an example, the nonionic surfactant includes at least one of cocamide, fatty alcohol polyoxyethylene ether, fatty alcohol, alkyl glucoside, cocamide methyl MEA, cocamide DEA, cocamide MEA, cocamide MIPA, lauramide DEA, lauramide MEA, lauramide MIPA, myristic amide DEA, myristic amide MEA, PEG-20 cocamide MEA, PEG-2 cocamide, PEG-3 cocamide, PEG-4 cocamide, PEG-5 cocamide, PEG-6 cocamide, PEG-7 cocamide, PEG-3 lauramide, PEG-5 lauramide, PEG-3 oleamide, PPG-2 cocamide and PPG-2 hydroxyethyl cocamide.

[0119] As an example, the cationic surfactant includes alkyl trimethyl ammonium chloride, alkyl trimethyl ammonium bromide, alkyl trimethyl methyl sulfate, alkyl dimethyl ethyl ammonium ethyl sulfate, fatty acid amidopropyl trimethyl ammonium chloride, fatty acid amidopropyl trimethyl ammonium bromide, fatty acid amidopropyl trimethyl ammonium methyl sulfate, fatty acid amidopropyl dimethyl ethyl ammonium ethyl sulfate, alkyl dihydroxyethyl methyl ammonium chloride, alkyl dihydroxyethyl methyl ammonium bromide, alkyl dihydroxyethyl methyl ammonium methyl sulfate, alkyl dihydroxyethyl ethyl ammonium ethyl sulfate, fatty acid amidopropyl dihydroxyethyl methyl ammonium chloride , fatty amide propyl dihydroxyethyl methyl ammonium bromide, fatty amide propyl dihydroxyethyl methyl ammonium methyl sulfate, fatty amide propyl dihydroxyethyl ethyl ammonium ethyl sulfate, fatty amide ethyl trimethyl ammonium chloride, fatty amide ethyl trimethyl ammonium bromide, fatty amide ethyl trimethyl ammonium methyl sulfate, fatty amide ethyl dimethyl ammonium ethyl ethyl sulfate, fatty amide ethyl dihydroxyethyl methyl ammonium chloride, fatty amide ethyl dihydroxyethyl methyl ammonium bromide, fatty amide ethyl dihydroxyethyl methyl ammonium methyl sulfate and fatty amide ethyl dihydroxyethyl ethyl ammonium ethyl sulfate.

[0120] In some embodiments of the present invention, based on the total mass of the daily chemical product, the mass proportion of the surfactant is 3%-50%, for example, 5%-45%, 10%-40%, 15%-35%, 20%-30%, 20%-25%, etc.

[0121] In some embodiments of the present invention, the functional aid includes at least one of vitamins, chelating agents, fragrances, whitening agents, enzymes, conditioners, thickeners, attractants, dyes, pigments, bleaching agents and pearlescent agents.

[0122] As an example, the chelating agent includes at least one of ethylenediaminetetraacetate, aminotriacetate, diethylenetriaminepentaacetic acid and its salts, glutamate tetraacetate, ethylenediamine disuccinate, citric acid, tartaric acid, gluconic acid, hydroxyethylethylenediaminetriacetic acid, dihydroxyethylglycine, organic polyphosphonic acid, polyacrylic acid, polymethacrylic acid, hydrolyzed polymaleic anhydride and fumaric acid-propylene sulfonic acid copolymer.

[0123] As an example, the conditioning agent includes at least one of cationic guar gum polymer, cationic non-guar galactomannan polymer, cationic modified starch polymer, copolymer of acrylamide monomer and cationic monomer, cationic cellulose polymer, polysiloxane, amino silicone oil and cationic cassia gum polymer.

[0124] As an example, the thickener includes at least one of modified hydroxyethyl cellulose, hydrophobically modified polyacrylate, hydrophobically modified polyacrylic acid, hydrophobically modified polyacrylamide, methyl glucose dioleate, sorbitan tetraoleate, sorbitan tetraoleate, pentaerythritol tetrastearate, propylene glycol oleate and distearate.

[0125] As an example, the pearlescent agent includes at least one of fatty acid glycol diester and fatty acid glycol monoester.

[0126] It should be noted that the vitamins, spices, whitening agents, enzymes, attractants, dyes, pigments, and bleaching agents in the functional additives of the present application are all conventional materials in the field of daily chemical products, and those skilled in the art can select them according to actual needs.

[0127] In some embodiments of the present invention, based on the total mass of the daily chemical product, the mass proportion of the functional additive is 0.01%-10%, for example, 0.05%-10%, 0.1%-10%, 0.5%-10%, 1%-10%, 2%-9%, 3%-8%, 4%-7%, 5%-6%, etc.

[0128] In some embodiments of the present invention, based on the total mass of the daily chemical product, the mass proportion of the solvent is 40%-96%, for example, 45%-96%, 50%-90%, 55%-85%, 60%-80%, 65%-75%, 65%-70%, etc.

[0129] As an example, the solvent includes at least one of water, ethanol, glycerol, propylene glycol, polyethylene glycol, and isopropyl alcohol.

[0130] The following embodiments of the present invention are described in detail. It should be noted that the following embodiments are illustrative and are intended only to explain the present invention and are not to be construed as limiting the present invention. In addition, unless otherwise expressly stated, all reagents used in the following embodiments are commercially available or can be synthesized according to methods described herein or known methods. Reaction conditions not listed are also readily available to those skilled in the art.

[0131] Example 1

[0132] (1) The method for preparing (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) comprises:

[0133] To a 250ml reactor, a 40% (mass concentration) aqueous sodium bisulfite solution (130.6 grams, 0.50 mol) was added, the pH was adjusted to 5.6, nitrogen was replaced, the pressure was 0 MPa, and the reaction was heated to 35°C. Propylene oxide (29.6 grams, 0.51 mol) was slowly added. After the addition was complete, the temperature was controlled to 65°C and the reaction was kept incubated for 1 hour. After completion of the reaction, the reaction product was purified by a PFP column (the volume ratio of ethanol and water in the mobile phase of the PFP column was controlled to be 12:88) to obtain a mixture comprising HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na, wherein the molar ratio of HO-CH(CH3)CH2-SO3Na to HO-CH2CH(CH3)-SO3Na was 93.5:6.5 (the product ratio can be obtained by nuclear magnetic resonance, as shown in FIG. Figure 2 and then dried to remove moisture.

[0134] (2) Coconut oil (82.0 g, 0.40 mol), methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) (65.1 g, 0.40 mol) obtained in step (1), and zinc methyl isethionate (0.8 g) were added to a 250 ml reactor, and an appropriate amount of nitrogen was introduced at a pressure of 0.01 MPa. The mixture was stirred and heated to 210.0°C for 8 hours. The reaction was then carried out while removing a portion of the unreacted fatty acid by vacuum distillation at a temperature of 215.0°C, a time of 7.0 hours, and a pressure of -0.04 MPa to obtain compound A (CH3CH2CH2(CH2CH2) 3-4 CH2CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3CH2CH2(CH2CH2) 3-4 The NMR spectrum of the CH2CH2-COO-CH2CH(CH3)-SO3Na) composition is as follows Figure 3 shown.

[0135] Compound A (CH3CH2CH2 (CH2CH2) 3-4 CH2CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3CH2CH2(CH2CH2) 3-4 The mass proportion of the residual fatty acids was 5.2%, and the residual methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) accounted for 3.7%. The residual compound A (CH3CH2CH2(CH2CH2) in the composition 3-4 CH2CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3CH2CH2(CH2CH2) 3-4 The molar ratio of CH2CH2-COO-CH2CH(CH3)-SO3Na) is 93.5:6.5 (the product ratio can be obtained by nuclear magnetic resonance).

[0136] Example 2

[0137] (1) The method for preparing methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) was the same as in Example 1, except that the volume ratio of ethanol to water in the mobile phase of the PFP column was controlled to 15:85, and the molar ratio of HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na was 92.5:7.5 (the product ratio can be obtained by nuclear magnetic resonance, as shown in Figure 2). Figure 4 As shown), and then dried to remove moisture;

[0138] (2) Myristic acid (88.0 g, 0.39 mol), methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) (66.8 g, 0.41 mol) obtained in step (1), and zinc phosphite (0.9 g) were added to a 250 ml reactor, and an appropriate amount of nitrogen was introduced at a pressure of 0.02 MPa. The mixture was stirred and heated to 215.0°C for 7.5 hours. A portion of the unreacted fatty acid was then removed by reduced pressure distillation at a temperature of 220.0°C for 6.8 hours at a pressure of -0.07 MPa to obtain compound A (CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The NMR spectrum of CH2-COO-CH2CH(CH3)-SO3Na) is as follows Figure 5As shown, the compound A (CH3 (CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The mass proportion of the residual fatty acids was 5.3%, the residual methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) was 1.9%, and the residual mass of the composition compound A (CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The molar ratio of CH2-COO-CH2CH(CH3)-SO3Na) is 92.5:7.5 (the product ratio can be obtained by nuclear magnetic resonance spectrum).

[0139] Example 3

[0140] (1) The method for preparing methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) was the same as in Example 1, except that the volume ratio of ethanol to water in the mobile phase of the PFP column was controlled to 19:81, and the molar ratio of HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na was 91.5:8.5 (the product ratio can be obtained by nuclear magnetic resonance, as shown in Figure 2). Figure 6 As shown), and then dried to remove moisture;

[0141] (2) To a 250 ml reactor, lauric acid (86.0 g, 0.43 mol), methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) (68.4 g, 0.42 mol) obtained in step (1), and zinc oxide (0.8 g) were added, and an appropriate amount of nitrogen was introduced at a pressure of 0.02 MPa. The mixture was stirred and heated to 215.0°C for 7.5 hours. The reaction was then carried out while removing a portion of the unreacted fatty acid by vacuum distillation at a temperature of 225.0°C for 6.5 hours at a pressure of -0.04 MPa. The resulting composition included compound A (CH3(CH2)9CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2)9CH2-COO-CH2CH(CH3)-SO3Na), and its NMR spectrum was as shown below. Figure 7As shown, the mass proportion of compound A (CH3(CH2)9CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2)9CH2-COO-CH2CH(CH3)-SO3Na) in the composition is 88.1%, the mass proportion of fatty acid residue is 5.4%, the mass proportion of methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) residue is 3.9%, and the molar ratio of compound A (CH3(CH2)9CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2)9CH2-COO-CH2CH(CH3)-SO3Na) in the composition is 91.5:8.5 (the product ratio can be obtained by nuclear magnetic resonance spectrum).

[0142] Example 4

[0143] (1) The method for preparing methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) was the same as in Example 1, except that the volume ratio of ethanol to water in the mobile phase of the PFP column was controlled to 24:76, and the molar ratio of HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na was 90.5:9.5 (the product ratio can be obtained by nuclear magnetic resonance, as shown in Figure 2). Figure 8 As shown), and then dried to remove moisture;

[0144] (2) Stearic acid (125.0 g, 0.44 mol), methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) (78.1 g, 0.48 mol) obtained in step (1), and zinc citrate (0.7 g) were added to a 250 ml reactor, and an appropriate amount of nitrogen was introduced at a pressure of 0.02 MPa. The mixture was stirred and heated to 225.0°C for 8 hours. The reaction was then continued while a portion of the unreacted fatty acid was removed by vacuum distillation at a temperature of 225.0°C for 7.5 hours at a pressure of -0.08 MPa to obtain compound A (CH3(CH2) 15 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 15 The composition of CH2-COO-CH2CH(CH3)-SO3Na) has an NMR spectrum as shown in FIG. Figure 9 As shown, the compound A (CH3 (CH2) 15 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 15The mass proportion of the residual fatty acids was 5.10%, and the residual methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) accounted for 5.5%. The residual compound A (CH3(CH2) 15 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 15 The molar ratio of CH2-COO-CH2CH(CH3)-SO3Na) is 90.5:9.5 (the product ratio can be obtained by nuclear magnetic resonance spectrum).

[0145] Example 5

[0146] (1) Same as Example 1;

[0147] (2) Hexanoic acid (46.5.0 g, 0.40 mol), methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) (65.1 g, 0.40 mol) obtained in step (1), and zinc methyl isethionate (0.4 g) were added to a 250 ml reactor, and an appropriate amount of nitrogen was introduced at a pressure of 0.01 MPa. The mixture was stirred and heated to 210.0°C for 8 hours. The reaction was then continued by vacuum distillation to remove a portion of the unreacted hexanoic acid at a temperature of 215.0°C for 7.0 hours at a pressure of -0.04 MPa to obtain a composition comprising compound A (CH3(CH2)3CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2)3CH2-COO-CH2CH(CH3)-SO3Na). The NMR spectrum of the composition is as follows: Figure 10 The mass proportion of compound A (CH3(CH2)3CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2)3CH2-COO-CH2CH(CH3)-SO3Na) in the composition is 88.2%, the mass proportion of fatty acid residue is 4.5%, the mass proportion of methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) residue is 6.4%, and the molar ratio of compound A (CH3(CH2)3CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2)3CH2-COO-CH2CH(CH3)-SO3Na) in the composition is 93.5:6.5 (the product ratio can be obtained by nuclear magnetic resonance).

[0148] Example 6

[0149] (1) Same as Example 1;

[0150] (2) To a 250 ml reactor, nonadecanoic acid (119.3 g, 0.40 mol), methyl isethionate salts (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) (65.1 g, 0.40 mol) obtained in step (1), and zinc methyl isethionate (0.8 g) were added, and an appropriate amount of nitrogen was introduced at a pressure of 0.01 MPa. The mixture was stirred and heated to 210.0°C for 8 hours. The reaction was then continued while a portion of the unreacted hexanoic acid was removed by vacuum distillation at a temperature of 215.0°C for 7.0 hours at a pressure of -0.04 MPa to obtain compound A (CH3(CH2) 16 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 16 The NMR spectrum of the CH2-COO-CH2CH(CH3)-SO3Na) composition is as follows Figure 11 As shown. Compound A (CH3 (CH2) 16 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 16 The mass proportion of the residual fatty acids was 5.5%, and the residual methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) accounted for 6.1%. The residual compound A (CH3(CH2) 16 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 16 The molar ratio of CH2-COO-CH2CH(CH3)-SO3Na) is 93.5:6.5 (the product ratio can be obtained by nuclear magnetic resonance).

[0151] Example 7

[0152] (1) Same as Example 1;

[0153] (2) Tetracosanoic acid (147.3 g, 0.40 mol), methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) (65.1 g, 0.40 mol) obtained in step (1), and zinc methyl isethionate (0.8 g) were added to a 250 ml reactor, and an appropriate amount of nitrogen was introduced at a pressure of 0.01 MPa. The mixture was stirred and heated to 210.0°C for 8 hours. The reaction was then carried out while removing a portion of the unreacted hexanoic acid by vacuum distillation at a temperature of 215.0°C for 7.0 hours at a pressure of -0.04 MPa to obtain compound A (CH3(CH2) 21 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 21 The NMR spectrum of the CH2-COO-CH2CH(CH3)-SO3Na) composition is as follows Figure 12 As shown. Compound A (CH3 (CH2) 21 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 21 The mass proportion of the residual fatty acids was 5.6%, and the residual methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) accounted for 6.0%. The residual compound A (CH3(CH2) 21 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 21 The molar ratio of CH2-COO-CH2CH(CH3)-SO3Na) is 93.5:6.5 (the product ratio can be obtained by nuclear magnetic resonance).

[0154] Comparative Example 1

[0155] (1) A 40% (mass concentration) aqueous sodium bisulfite solution (130.6 g, 0.50 mol) was added to a 250 ml reactor, the pH was adjusted to 6.7-7.5, nitrogen was replaced, the pressure was 0.45 MPa, and the reaction was heated to 70° C., and propylene oxide (30.2 g, 0.52 mol) was slowly added. After the addition was completed, the temperature was controlled to 80° C. and the reaction was kept warm for 1.5 hours. After the reaction was completed, the mixture was spray-dried to obtain a mixture including HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na, wherein the molar ratio of HO-CH(CH3)CH2-SO3Na to HO-CH2CH(CH3)-SO3Na was 94:6 (the product ratio can be obtained by nuclear magnetic resonance, as shown in FIG. Figure 13 and then dried to remove moisture.

[0156] (2) Stearic acid (125.0 g, 0.44 mol), methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) (68.4 g, 0.42 mol) obtained in step (1), and zinc citrate (0.9 g) were added to a 250 ml reactor, and an appropriate amount of nitrogen was introduced at a pressure of 0 MPa. The mixture was stirred and heated to 215.0°C for 6 hours, and then the stearic acid was removed by vacuum distillation at 10 mmHg to obtain compound A (CH3(CH2) 15 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 15 The composition of CH2-COO-CH2CH(CH3)-SO3Na) has an NMR spectrum as shown in FIG. Figure 14 As shown, the compound A (CH3 (CH2) 15 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 15 CH2-COO-CH2CH(CH3)-SO3Na) accounts for 84.3% by mass, the residual fatty acid accounts for 6.1% by mass, the residual methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) accounts for 6.5% by mass, and the residual compound A (CH3(CH2) 15 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 15 The molar ratio of CH2-COO-CH2CH(CH3)-SO3Na) is 93.7:6 (the product ratio can be obtained by nuclear magnetic resonance spectrum).

[0157] Comparative Example 2

[0158] (1) A 40% (mass concentration) aqueous sodium bisulfite solution (130.6 g, 0.50 mol) was added to a 250 ml reactor, the pH was adjusted to 6.7-7.5, nitrogen was replaced, the pressure was 0.45 MPa, and the reaction mixture was heated to 50° C., and propylene oxide (30.2 g, 0.52 mol) was slowly added. After the addition was completed, the temperature was controlled to 77° C. and the reaction was kept warm for 1.5 hours. After the reaction was completed, the mixture was dried by spray powder to obtain a mixture including HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na, wherein the molar ratio of HO-CH(CH3)CH2-SO3Na to HO-CH2CH(CH3)-SO3Na was 94.5:5.5 (the product ratio can be obtained by nuclear magnetic resonance, as shown in FIG. Figure 15 and then dried to remove moisture.

[0159] (2) Myristic acid (98.0 g, 0.43 mol), methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) (68.4 g, 0.42 mol) obtained in step (1), and zinc phosphite (0.7 g) were added to a 250 ml reactor, and an appropriate amount of nitrogen was introduced at a pressure of 0 MPa. The mixture was stirred and heated to 225.0°C for 7 hours, and then the myristic acid was removed by vacuum distillation at 15 mmHg to obtain compound A (CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The composition of CH2-COO-CH2CH(CH3)-SO3Na) has an NMR spectrum as shown in FIG. Figure 16 As shown, the compound A (CH3 (CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The mass proportion of the residual fatty acids was 6.6%, the residual methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) accounted for 6%, and the residual mass of the composition compound A (CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The molar ratio of CH2-COO-CH2CH(CH3)-SO3Na) is 94.5:5.5 (the product ratio can be obtained by nuclear magnetic resonance spectrum).

[0160] Comparative Example 3

[0161] (1) A 40% (mass concentration) aqueous sodium bisulfite solution (135.8 g, 0.52 mol) was added to a 250 ml reactor, the pH was adjusted to 6.7-7.5, nitrogen was replaced, the pressure was 0.45 MPa, and the reaction was heated to 40° C., and propylene oxide (30.2 g, 0.52 mol) was slowly added. After the addition was completed, the temperature was controlled to 76° C. and the reaction was kept warm for 1.5 hours. After the reaction was completed, the mixture was dried by spray powder to obtain a mixture including HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na, wherein the molar ratio of HO-CH(CH3)CH2-SO3Na to HO-CH2CH(CH3)-SO3Na was 95.0:5.0 (the product ratio can be obtained by nuclear magnetic resonance, such as Figure 17 and then dried to remove moisture.

[0162] (2) Myristic acid (98.0 g, 0.43 mol), methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) (68.4 g, 0.42 mol) obtained in step (1), and zinc citrate (0.8 g) were added to a 250 ml reactor, and an appropriate amount of nitrogen was introduced at a pressure of 0 MPa. The mixture was stirred and heated to 215.0°C for 7 hours, and then the myristic acid was removed by vacuum distillation at 15 mmHg to obtain compound A (CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The composition of CH2-COO-CH2CH(CH3)-SO3Na) has an NMR spectrum as shown in FIG. Figure 18 As shown, the compound A (CH3 (CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The mass proportion of the residual fatty acids was 6.0%, the residual methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) was 6.2%, and the residual mass of the composition compound A (CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The molar ratio of CH2-COO-CH2CH(CH3)-SO3Na) is 95.0:5.0 (the product ratio can be obtained by nuclear magnetic resonance spectrum).

[0163] Comparative Example 4

[0164] (1) A 40% (mass concentration) aqueous sodium bisulfite solution (130.6 g, 0.50 mol) was added to a 250 ml reactor, the pH was adjusted to 6.7-7.5, nitrogen was replaced, the pressure was 0.45 MPa, and the reaction was heated to 82° C., and propylene oxide (29.0 g, 0.50 mol) was slowly added. After the addition was completed, the temperature was controlled to 82° C. and the reaction was kept warm for 1.5 hours. After the reaction was completed, the mixture was spray-dried to obtain a mixture including HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na, wherein the molar ratio of HO-CH(CH3)CH2-SO3Na to HO-CH2CH(CH3)-SO3Na was 89.5:10.5 (the product ratio can be obtained by nuclear magnetic resonance, as shown in FIG. Figure 19 and then dried to remove moisture.

[0165] (2) Stearic acid (125.0 g, 0.44 mol), methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) (68.4 g, 0.42 mol) obtained in step (1), and zinc citrate (0.7 g) were added to a 250 ml reactor, and an appropriate amount of nitrogen was introduced at a pressure of 0 MPa. The mixture was stirred and heated to 215.0°C for 7 hours, and then the stearic acid was removed by vacuum distillation at 10 mmHg to obtain compound A (CH3(CH2) 15 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 15 The composition of CH2-COO-CH2CH(CH3)-SO3Na) has an NMR spectrum as shown in FIG. Figure 20 As shown, the compound A (CH3 (CH2) 15 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 15 CH2-COO-CH2CH(CH3)-SO3Na) accounts for 84.9% by mass, the residual fatty acids account for 6.6% by mass, the residual methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) accounts for 6.7% by mass, and the residual compound A (CH3(CH2) 15 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 15 The molar ratio of CH2-COO-CH2CH(CH3)-SO3Na) is 89.5:10.5 (the product ratio can be obtained by nuclear magnetic resonance spectrum).

[0166] Comparative Example 5

[0167] (1) A 40% (mass concentration) aqueous sodium bisulfite solution (130.6 g, 0.50 mol) was added to a 250 ml reactor, the pH was adjusted to 6.7-7.5, nitrogen was replaced, the pressure was 0.45 MPa, and the reaction was heated to 84° C., and propylene oxide (30.2 g, 0.52 mol) was slowly added. After the addition was completed, the temperature was controlled to 84° C. and the reaction was kept warm for 2.5 hours. After the reaction was completed, the mixture was spray-dried to obtain a mixture including HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na, wherein the molar ratio of HO-CH(CH3)CH2-SO3Na to HO-CH2CH(CH3)-SO3Na was 86.5.5:13.5 (the product ratio can be obtained by nuclear magnetic resonance, as shown in FIG. Figure 21 and then dried to remove moisture.

[0168] (2) Myristic acid (95.7 g, 0.42 mol), methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) (68.4 g, 0.42 mol) obtained in step (1), and zinc phosphite (0.85 g) were added to a 250 ml reactor, and an appropriate amount of nitrogen was introduced at a pressure of 0.1 MPa. The mixture was stirred and heated to 225.0°C for 7 hours, and then the myristic acid was removed by vacuum distillation at 20 mmHg to obtain compound A (CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The composition of CH2-COO-CH2CH(CH3)-SO3Na) has an NMR spectrum as shown in FIG. Figure 22 As shown, the compound A (CH3 (CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The mass proportion of the residual fatty acids was 6.0%, the residual methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) was 6.4%, and the residual mass of the composition compound A (CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The molar ratio of CH2-COO-CH2CH(CH3)-SO3Na) is 86.5.5:13.5 (the product ratio can be obtained by nuclear magnetic resonance spectrum).

[0169] Comparative Example 6

[0170] (1) A 40% (mass concentration) aqueous sodium bisulfite solution (130.6 g, 0.50 mol) was added to a 250 ml reactor, the pH was adjusted to 6.7-7.5, nitrogen was replaced, the pressure was 0.45 MPa, and the reaction was heated to 85° C., and propylene oxide (30.2 g, 0.52 mol) was slowly added. After the addition was completed, the temperature was controlled to 85° C. and the reaction was kept warm for 2.0 hours. After the reaction was completed, the mixture was dried by spray powder to obtain a mixture including HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na, wherein the molar ratio of HO-CH(CH3)CH2-SO3Na to HO-CH2CH(CH3)-SO3Na was 85.5.5:14.5 (the product ratio can be obtained by nuclear magnetic resonance, as shown in FIG. Figure 23 and then dried to remove moisture.

[0171] (2) Myristic acid (95.7 g, 0.42 mol), methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) (68.4 g, 0.42 mol) obtained in step (1), and zinc oxide (0.85 g) were added to a 250 ml reactor. An appropriate amount of nitrogen was introduced at a pressure of 0.05 MPa. The mixture was stirred and heated to 225.0°C. The reaction was carried out for 7 hours. The myristic acid was then removed by vacuum distillation at 20 mmHg to obtain compound A (CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The composition of CH2-COO-CH2CH(CH3)-SO3Na) has an NMR spectrum as shown in FIG. Figure 24 As shown, the compound A (CH3 (CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The mass proportion of the residual fatty acids was 5.7%, the residual methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) accounted for 6.5%, and the residual mass of the composition compound A (CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The molar ratio of CH2-COO-CH2CH(CH3)-SO3Na) is 85.5:14.5 (the product ratio can be obtained by nuclear magnetic resonance spectrum).

[0172] Comparative Example 7

[0173] (1) A 40% (mass concentration) aqueous sodium bisulfite solution (130.6 g, 0.50 mol) was added to a 250 ml reactor, the pH was adjusted to 6.7-7.5, nitrogen was replaced, the pressure was 0.45 MPa, and the reaction was heated to 87° C., and propylene oxide (30.2 g, 0.52 mol) was slowly added. After the addition was completed, the temperature was controlled to 87° C. and the reaction was kept warm for 2.5 hours. After the reaction was completed, the mixture was dried by spray powder to obtain a mixture including HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na, wherein the molar ratio of HO-CH(CH3)CH2-SO3Na to HO-CH2CH(CH3)-SO3Na was 85.0:15.0 (the product ratio can be obtained by nuclear magnetic resonance, as shown in FIG. Figure 25 and then dried to remove moisture.

[0174] (2) Myristic acid (95.7 g, 0.42 mol), methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) (68.4 g, 0.42 mol) obtained in step (1), and zinc phosphite (0.95 g) were added to a 250 ml reactor, and an appropriate amount of nitrogen was introduced at a pressure of 0.1 MPa. The mixture was stirred and heated to 225.0°C for 7 hours, and then the myristic acid was removed by vacuum distillation at 20 mmHg to obtain compound A (CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 The composition of CH2-COO-CH2CH(CH3)-SO3Na) has an NMR spectrum as shown in FIG. Figure 26 As shown, the compound A (CH3 (CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11 CH2-COO-CH2CH(CH3)-SO3Na) accounted for 85.3% by mass, the residual fatty acids accounted for 6.4% by mass, the residual methyl isethionate (HO-CH(CH3)CH2-SO3Na and HO-CH2CH(CH3)-SO3Na) accounted for 6.7% by mass, and the composition compound A (CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3Na) and compound B (CH3(CH2) 11The molar ratio of CH2-COO-CH2CH(CH3)-SO3Na) is 85.0:15.0 (the product ratio can be obtained by nuclear magnetic resonance spectrum).

[0175] The properties of the compositions obtained in Examples 1-7 and Comparative Examples 1-7 were tested, as follows:

[0176] 1. 5α-reductase type 1 inhibitory effect test:

[0177] Current research suggests that 5α-reductase type 1 is most closely related to oil secretion. Based on this, the test is performed as follows:

[0178] (1) Experimental materials:

[0179] a. Cell line: human sebaceous gland cells;

[0180] b. Culture medium: pyruvate-free DMEM medium containing 10% FBS;

[0181] c. Maintenance medium: pyruvate-free DMEM medium containing 1% FBS;

[0182] d. Test conditions: incubator temperature 37±1°C, humidity 90±5%, CO2 5±1% (volume concentration);

[0183] e. MTT solution: Prepare MTT stock solution with PBS to a concentration of 5 mg / mL, filter sterilize using a 0.22 μm syringe filter, and store at -20°C.

[0184] f. TRIzol reagent.

[0185] (2) Experimental steps:

[0186] SRD5A1 gene expression test:

[0187] a. Conventional cell culture: Inoculate the cell suspension into a 6-well plate and culture for 18-24 hours.

[0188] b. Discard the original culture medium in the wells, add maintenance medium containing different test samples and maintenance medium without test samples according to the group, with 3 parallels per group, and expose for 24 hours.

[0189] c. Harvest 1-5×10 cells 6cfu / g, transfer to a 1.5mL centrifuge tube, add 1mL Trizol, mix well, and let stand at room temperature for 5 minutes. Add 0.2mL chloroform, shake for 15 seconds, and let stand for 2 minutes. Centrifuge at 4℃, 12000g×15 minutes, and remove the supernatant. Add 0.5mL isopropanol, gently mix the liquid in the tube, and let stand for 10 minutes. Centrifuge at 4℃, 12000g×10 minutes, and discard the supernatant. Add 1mL 75% ethanol and gently wash the precipitate. Centrifuge at 4℃, 7500g×5 minutes, and discard the supernatant. Let dry and add an appropriate amount of DEPC H2O to dissolve.

[0190] d. The RNA sample extracted in the previous step was reverse transcribed into cDNA, and then subjected to qPCR detection and analysis. The primers and amplification system for qPCR detection are shown in Tables 1 and 2.

[0191] Table 1 Primer design

[0192] name sequence F-SRD5A1 TACGGGCATCGGTGCTTAAT R-SRD5A1 CATGCCCGTTAACCACAAGC GAPDH-F AATGACCCCTTCATTGAC GAPDH-R TCCACGACGTACTCAGCGC

[0193] Table 2 Reaction system

[0194] cDNA 1 μL F-SRD5A1 (10 μM) 0.4μL R-SRD5A1 (10 μM) 0.4μL 2×PerfectStar aPCR SuperMix 10 μL Nuclease-Water 8.2μL

[0195] (3) Data Analysis

[0196] All data were expressed as mean ± standard deviation. SPSS 20.0 statistical software was used to analyze the experimental data. The difference was considered statistically significant when p < 0.05.

[0197] 2. 5α-reductase type 2 inhibitory effect test:

[0198] Androgenic alopecia is caused by the conversion of testosterone into the more active dihydrotestosterone (DHT) through the action of 5α-reductase type 2. This DHT is sensitive to hair follicles, affecting their development and leading to hair loss. In vitro analysis can be used to determine whether a test sample can inhibit 5α-reductase type 2, thereby inhibiting the production of DHT, as a basis for determining whether it has anti-hair loss efficacy.

[0199] The specific testing process included: a 2 mL reaction system containing: 0.25 mL of phosphate buffer, 0.70 mL of enzyme extract, 0.1 mL of testosterone solution (0.5 mg / mL), 0.35 mL of NADPH solution (0.8 mg / mL), and 0.6 mL of 10% ethanol (in the complete reaction group, finasteride in the positive group, and sample solution in the sample group). In the control group, the enzyme extract was replaced with phosphate buffer, and the reaction was terminated by the addition of 2.0 mL of dichloromethane. The complete reaction group, the positive group, and the sample group were reacted at 37°C for 30 minutes. After the reaction, 2.0 mL of dichloromethane was added to stop the reaction, and the reaction was shaken for 1 minute and centrifuged at 5000 rpm for 10 minutes. The upper aqueous phase was removed, and approximately 1.0 mL of the organic phase was removed and evaporated to dryness. The residue was dissolved in 1.0 mL of methanol, and the testosterone peak area (T) was determined by high-performance liquid chromatography. Three parallel groups were set up for each reaction.

[0200] according to The 5α-reductase type 2 inhibition rate data were calculated to evaluate the inhibitory effect of the sample on 5α-reductase type 2.

[0201] The test results are as follows Figures 27-28 As shown, Figure 27 (The control group is a blank group, i.e., no composition is added) The changing trend of the effects of the compositions of Examples 1-7 and Comparative Examples 1-7 on SRD5A1 gene expression is shown. It can be seen that the compositions of Examples 1-7 can downregulate SRD5A1 gene expression, thereby inhibiting 5α-reductase type 1, and thus achieving an oil control effect. Figure 28 The variation trend of the inhibitory effect of the compositions of the positive group, Examples 1-7 and Comparative Examples 1-7 on 5α-reductase type 2 is shown. It can be seen that the compositions of Examples 1-7 can inhibit 5α-reductase type 2, thereby achieving the anti-hair loss effect.

[0202] Experimental Example 1

[0203] (1) Detergent formula components are shown in Table 3

[0204] Table 3 Detergent formula

[0205]

[0206] (2) The preparation method comprises:

[0207] a. Mix all the materials in component A and heat and stir to dissolve evenly;

[0208] b. After component A is evenly dissolved, add component B and continue heating and stirring to dissolve evenly;

[0209] c. After component B is evenly dissolved, cool it down to room temperature, add component C, and stir evenly to obtain detergent.

[0210] Detergent composition of the control group:

[0211] Table 4 Detergent formula for control group

[0212]

[0213] The compositions of Examples 1-7 and Comparative Examples 1-7 were added to the detergent of Experimental Example 1, respectively. Then, the inhibitory effects of the obtained detergents and the control group on 5α-reductase type 1 and 5α-reductase type 2 were tested (the test method refers to the test method for the inhibitory effects of the above compositions on 5α-reductase type 1 and 5α-reductase type 2). The test results are shown in FIG. Figures 29-30 , Figure 29 The changing trends of the effects of the compositions of Examples 1-7 and Comparative Examples 1-7, respectively configured with corresponding detergents and a control group on SRD5A1 gene expression are shown. It can be seen that the detergents corresponding to the compositions of Examples 1-7 can downregulate SRD5A1 gene expression, thereby exhibiting a higher inhibitory effect on 5α-reductase type 1, further demonstrating that the detergents corresponding to the compositions of Examples 1-7 have excellent oil control effects. Figure 30 The changing trends of the inhibitory effects of the corresponding detergents and the positive group of Examples 1-7 and Comparative Examples 1-7 on 5α-reductase type 2 are shown. It can be seen that the detergents corresponding to the compositions of Examples 1-7 and the detergent of the positive group have a high inhibitory effect on 5α-reductase type 2, thereby proving that the detergents corresponding to the compositions of Examples 1-7 have excellent anti-hair loss effects.

[0214] Experimental Example 2

[0215] (1) Detergent formula components are shown in Table 5

[0216] Table 5 Detergent formula

[0217]

[0218]

[0219] (2) The preparation method is the same as that of Experimental Example 1.

[0220] The composition of the detergent in the control group was the same as that in Experimental Example 1.

[0221] The compositions of Examples 1-7 and Comparative Examples 1-7 were respectively added to the detergent of Experimental Example 2, and then the 5α-reductase type 1 and 5α-reductase type 2 inhibitory effects of the resulting detergents and the control group were tested (the test method was the same as that of Experimental Example 1). The test results are shown in Table 4.

[0222] Table 6

[0223]

[0224] Table 6 shows the detergents configured with the compositions of Examples 1-7 and Comparative Examples 1-7, respectively, and the trends in their inhibitory effects on 5α-reductase type 1 and 5α-reductase type 2. It can be seen that the detergents corresponding to the compositions of Examples 1-7 and the detergent in the control group all have high inhibitory effects on 5α-reductase type 1, demonstrating that the detergents corresponding to the compositions of Examples 1-7 have excellent oil control effects. Furthermore, the detergents corresponding to the compositions of Examples 1-7 and the detergent in the positive group all have high inhibitory effects on 5α-reductase type 2, demonstrating that the detergents corresponding to the compositions of Examples 1-7 have excellent anti-hair loss effects.

[0225] Experimental Example 3

[0226] (1) Detergent formula components are shown in Table 5

[0227] Table 7 Detergent formula

[0228]

[0229] (2) The preparation method is the same as that of Experimental Example 1.

[0230] The composition of the detergent in the control group was the same as that in Experimental Example 1.

[0231] The compositions of Examples 1-7 and Comparative Examples 1-7 were respectively added to the detergent of Experimental Example 2, and then the 5α-reductase type 1 and 5α-reductase type 2 inhibitory effects of the resulting detergents and the control group were tested (the test method was the same as that of Experimental Example 1). The test results are shown in Table 8.

[0232] Table 8

[0233]

[0234]

[0235] Table 8 shows the trends in the inhibitory effects of the corresponding detergents for the compositions of Examples 1-7 and Comparative Examples 1-7, as well as the control group, on 5α-reductase type 1 and 5α-reductase type 2. It can be seen that the detergents corresponding to the compositions of Examples 1-7 and the detergent in the positive group all have high inhibitory effects on 5α-reductase type 1, demonstrating that the detergents corresponding to the compositions of Examples 1-7 have excellent oil control effects. At the same time, the detergents corresponding to the compositions of Examples 1-7 and the detergent in the control group all have high inhibitory effects on 5α-reductase type 2, demonstrating that the detergents corresponding to the compositions of Examples 1-7 have excellent anti-hair loss effects.

[0236] In the description of this specification, the description with reference to the terms "one embodiment", "some embodiments", "example", "specific example", or "some examples" means that the specific features, structures, materials or characteristics described in conjunction with the embodiment or example are included in at least one embodiment or example of the present application. In this specification, the schematic representations of the above terms do not necessarily refer to the same embodiment or example. Moreover, the specific features, structures, materials or characteristics described can be combined in any one or more embodiments or examples in a suitable manner. In addition, those skilled in the art can combine and combine different embodiments or examples described in this specification and features of different embodiments or examples without contradiction.

[0237] Although the embodiments of the present application have been shown and described above, it can be understood that the above embodiments are exemplary and cannot be understood as limitations on the present application. Ordinary technicians in this field can change, modify, replace and modify the above embodiments within the scope of the present application.

Claims

1. A composition, characterized in that Comprising compound A and compound B, The chemical formula of compound A is R-COO-CH(CH3)CH2-SO3X, the chemical formula of compound B is R-COO-CH2CH(CH3)-SO3X, R is a hydrocarbon group with 5-23 carbon atoms, X includes a hydrogen atom, an alkali metal ion, an alkaline earth metal ion, an aluminum ion, a zinc ion or an ammonium ion, and the molar ratio of compound A to compound B is (90.5-93.5):(6.5-9.5).

2. The composition according to claim 1, characterized in that The R includes an alkyl group having 5 to 17 carbon atoms.

3. The composition according to claim 1 or 2, characterized in that The compound A comprises at least one of the following: CH3CH2CH2(CH2CH2) 3-4 CH2CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2) 11 CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2)9CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2) 15 CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2) 16 CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2) 21 CH2-COO-CH(CH3)CH2-SO3X, CH3(CH2)3CH2-COO-CH(CH3)CH2-SO3X.

4. The composition according to claim 1 or 2, characterized in that The compound B comprises at least one of the following: CH3CH2CH2(CH2CH2) 3-4 CH2CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2) 11 CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2)9CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2) 15 CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2) 16 CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2) 21 CH2-COO-CH2CH(CH3)-SO3X, CH3(CH2)3CH2-COO-CH2CH(CH3)-SO3X.

5. The composition according to claim 1, characterized in that Based on the total mass of the composition, the total mass of the compound A and the compound B accounts for no less than 80%, preferably 80%-93%.

6. The composition according to claim 1 or 2, characterized in that At least one of the following conditions is met: Based on the total mass of the composition, the mass proportion of fatty acids is no more than 7%; Based on the total mass of the composition, the total mass of HO-CH(CH3)CH2-SO3X and HO-CH2CH(CH3)-SO3X accounts for no more than 7%; Based on the total mass of the composition, the mass proportion of water is no more than 1%.

7. A method for preparing the composition according to any one of claims 1 to 6, characterized in that: include: (1) subjecting HSO3X and propylene oxide to a ring-opening reaction to obtain a mixture comprising HO-CH(CH3)CH2-SO3X and HO-CH2CH(CH3)-SO3X; (2) adjusting the molar ratio of HO-CH(CH3)CH2-SO3X and HO-CH2CH(CH3)-SO3X in the mixture to (90.5-93.5):(6.5-9.5); (3) reacting the adjusted mixture obtained in step (2) with a fatty acid in the presence of a catalyst to obtain a composition comprising compound A and compound B.

8. The method according to claim 7, characterized in that In step (1), the ring-opening reaction satisfies one or more of the following: The ring-opening reaction temperature is 35°C-75°C; The ring-opening reaction time is 0.5 hours to 1 hour; The ring-opening reaction pressure is 0-0.04 MPa; The initial pH of the ring-opening reaction is 5.6-6.6; The molar ratio of HSO3X to propylene oxide is 1:(1-1.05).

9. The method according to claim 7, characterized in that Step (2) is performed as follows: The mixture was supplied to a chromatographic column for isocratic elution, using ethanol as mobile phase A and water as mobile phase B. Optionally, the volume ratio of the mobile phase A to the mobile phase B is (12-24):(88-76).

10. The method according to claim 7, characterized in that In step (3), the fatty acid includes a fatty acid having 6 to 24 carbon atoms; Optionally, the fatty acid comprises at least one of caproic acid, caprylic acid, capric acid, coconut acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, erucic acid and lignoceric acid; Optionally, the molar ratio of the adjusted mixture to the fatty acid is 1:(0.9-1.1).

11. The method according to claim 7 or 10, characterized in that In step (3), the catalyst comprises at least one of p-toluenesulfonic acid, p-toluenesulfonate, methylisothionate, methylisothionate, phosphorous acid, phosphite, sulfuric acid, sulfate, citric acid, citrate, zirconium oxide, magnesium oxide, zinc oxide and aluminum oxide; Optionally, the added mass proportion of the catalyst is 0.2%-0.9% based on the total mass of the fatty acid and the adjusted mixture; Optionally, the reaction temperature is 205°C-235°C; Optionally, the reaction time is 6.5 hours to 8.5 hours; Optionally, the reaction pressure is 0-0.05 MPa.

12. The method according to claim 7, characterized in that Also includes: As the adjusted mixture reacts with fatty acid in the presence of a catalyst, the system is subjected to reduced pressure distillation; Optionally, the temperature of the reduced pressure distillation is 205°C-235°C; Optionally, the time of the reduced pressure distillation is 4 hours to 8 hours; Optionally, the pressure of the reduced pressure distillation is -0.04 MPa to -0.09 MPa.

13. Use of the composition according to any one of claims 1 to 6 or the composition obtained by the method according to any one of claims 7 to 12 in inhibiting 5α-reductase.

14. Use of the composition according to any one of claims 1 to 6 or the composition obtained by the method according to any one of claims 7 to 12 in the field of preparing daily chemical products.

15. The use according to claim 14, characterized in that The daily chemical product is used for inhibiting 5α-reductase.

16. The use according to claim 14, characterized in that The daily chemical product is used for preventing hair loss and controlling oil.

17. A daily chemical product, characterized in that: The invention comprises the composition according to any one of claims 1 to 6 or a composition obtained by the method according to any one of claims 7 to 12.

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