A kind of azelaic acid organosilicon supramolecular ion salt and preparation method thereof

Abstract

The present invention discloses a supramolecular ionic salt of azelaic acid and a preparation method thereof, and belongs to the field of supramolecular technology. The present invention adopts azelaic acid and γ-aminopropyltriethoxysilane to form a liquid ionic salt through supramolecular action, which effectively improves the water solubility of azelaic acid, and can achieve high-content (46wt%) azelaic acid ionic salt and any ratio of water miscibility, which greatly facilitates the practicality of azelaic acid in product formulas, while ensuring its effective concentration. The γ-aminopropyltriethoxysilane in the supramolecular ionic salt of the present invention synergistically improves the softness of azelaic acid and expands the application of azelaic acid in hair products.

Description

Technical Field

[0001] The invention relates to a supramolecular ion salt of azelaic acid organosilicon and a preparation method thereof, belonging to the technical field of supramolecular ions. Background Art

[0002] Azelaic acid is found in cereals such as rye, barley and wheat. It has anti-inflammatory, acne-removing, whitening and scar-removing effects. Azelaic acid can brighten the skin tone, significantly improve the uniformity of skin texture and reduce facial spots. Azelaic acid itself is a weak acid that has the ability to dissolve keratin, control excessive keratinization of hair follicles, partially dissolve acne and reduce the formation of acne. Azelaic acid has a good antibacterial effect on two common bacteria that cause infection on the skin surface, Propionibacterium acnes and Staphylococcus epidermidis. It can also inhibit cell oxidative metabolism and scavenge free radicals to inhibit inflammation.

[0003] However, the solubility of azelaic acid in water, common solvents and solubilizers is low, which limits its application. At present, the amount of azelaic acid added to cosmetics on the market is usually as high as 15-20%. At such an amount, most of them can only form a paste, and cannot form a transparent, uniform and stable liquid at all. It is difficult for commonly used solubilizers or methods to reach the recommended amount of azelaic acid, and the solubility of azelaic acid in water and oil solvents is not ideal. Therefore, researchers need to find more ways to increase the solubility of azelaic acid in order to better utilize the various functions of azelaic acid. At the same time, there are almost no reports on the market about the use of azelaic acid in hair cosmetics to improve softness.

[0004] In order to improve the water solubility of azelaic acid, patent CN 113248364A discloses a method of using alkaline substances (such as theophylline, echinine, carnitine, etc.) and azelaic acid to form salts, thereby increasing the water solubility of azelaic acid. However, the preparation process requires a large amount of organic solvents and the process is relatively complicated; patent CN 112624918A discloses a co-crystal of azelaic acid and an organic base and a preparation method thereof, which prepares a solid co-crystal in an organic solvent under an inert gas, and then needs to undergo a series of operations such as membrane filtration, recrystallization, and removal of organic solvents to obtain the target co-crystal, which is not environmentally friendly and has a complicated process, and the patent does not clearly indicate the specific solubilization value of azelaic acid; patent CN 110669226A discloses a method for preparing a polyethylene glycol / propylene glycol / azelaic acid supramolecular system, in which propylene glycol and polyethylene glycol are used as solvents to first dissolve azelaic acid, and then the dissolved system is added to a large amount of water while hot. Propylene glycol and polyethylene glycol are commonly used solvents and solubilizers in cosmetic formulas. This method is essentially the thermal dissolution of azelaic acid under the solubilization of conventional alcohol and polyethylene glycol, so the solubility of azelaic acid can only be increased by 3.33 times at most, that is, about 8g / L; CN 110272353 B discloses a capsaicin-azelaic acid ion salt with whitening and antioxidant functions. The preparation of the ion salt requires the pre-solubilization of azelaic acid with a solvent and then reacts with capsaicin. At the same time, the ion salt is solid, so after the preparation is completed, it needs to be recrystallized and dried to obtain the target ion salt. The whole process takes 75 hours. More importantly, it does not indicate whether azelaic acid can be effectively solubilized. Summary of the invention

[0005] [Technical issues]

[0006] The current method does not significantly improve the solubility of azelaic acid;

[0007] Conventional γ-aminopropyltriethoxysilane is directly added to cosmetics without combining with other substances;

[0008] Currently, there are few reports on the market regarding the use of azelaic acid in hair cosmetics to improve smoothness.

[0009] [Technical solution]

[0010] In order to solve the above problems, the present invention selects a specific γ-aminopropyltriethoxysilane and a specific azelaic acid to prepare a supramolecular ion salt, which aims to improve the water solubility of azelaic acid while synergistically enhancing its softening effect, in order to expand its application in hair cosmetics.

[0011] γ-aminopropyltriethoxysilane is a common organosilicon compound. In cosmetics, it can play a variety of functional roles. First, γ-aminopropyltriethoxysilane can be used as a thickener and emulsifier. It can improve the texture and stability of cosmetics, increase their viscosity and stickiness, and make them easier to use and apply. In addition, it can form an emulsion between oil and water, help mix immiscible ingredients, and provide better dispersibility. Secondly, γ-aminopropyltriethoxysilane also has moisturizing and emollient functions. It can form a thin film on the skin surface, reduce water evaporation, and provide long-lasting moisturizing effects. At the same time, because of the presence of organosilicon structure, γ-aminopropyltriethoxysilane can also be used in shampoo products to enhance the softness of hair.

[0012] The first object of the present invention is to provide a supramolecular ionic salt of organosilicon with azelaic acid, the structural formula of which is as follows:

[0013]

[0014] In one embodiment, azelaic acid and γ-aminopropyltriethoxysilane form a liquid ionic salt through supramolecular action. The ionic salt is miscible with water in any proportion and can effectively improve the water solubility of azelaic acid.

[0015] In one embodiment, the supramolecular ionic salt does not affect the antibacterial property of azelaic acid, and can synergistically impart its softening effect.

[0016] The second object of the present invention is to provide a method for preparing azelaic acid organosilicon supramolecular ion salt, comprising the following steps:

[0017] Azelaic acid and γ-aminopropyltriethoxysilane are mixed in a molar ratio of 1:1 or 1:2, and stirred and heated or subjected to constant temperature ultrasound to obtain the azelaic acid organosilicon supramolecular ion salt.

[0018] In one embodiment, the atmosphere for stirring, heating or constant temperature ultrasound is nitrogen or natural air.

[0019] In one embodiment, the temperature of stirring heating or constant temperature ultrasound is 20-80°C.

[0020] In one embodiment, the stirring heating or constant temperature ultrasound time is 5 to 40 minutes.

[0021] In one embodiment, the rotation speed of stirring and heating is 200-1000 rpm, and the power of constant temperature ultrasound is 200-800W.

[0022] The third object of the present invention is the application of the azelaic acid organosilicon supramolecular ion salt of the present invention in the field of cosmetics or pharmacy.

[0023] The fourth object of the present invention is to provide a shampoo and hair care product with antibacterial and softening properties, which contains the azelaic acid organosilicon supramolecular ion salt of the present invention.

[0024] In one embodiment, the amount of azelaic acid organosilicon supramolecular ion salt is 0.1 to 30 wt %.

[0025] In one embodiment, the hair washing and hair care products include hair care essence, shampoo, hair mask and the like.

[0026] A fifth object of the present invention is a method for improving the softness of hair, which uses the azelaic acid organosilicon supramolecular ion salt of the present invention.

[0027] [Beneficial Effects]

[0028] (1) The present invention uses azelaic acid and γ-aminopropyltriethoxysilane to form a liquid ionic salt through supramolecular action, which effectively improves the water solubility of azelaic acid and can achieve miscibility of high-content (46wt%) azelaic acid ionic salt with water in any ratio, greatly facilitating the practicality of azelaic acid in product formulations while ensuring its effective concentration.

[0029] (2) The γ-aminopropyltriethoxysilane in the supramolecular ion salt of the present invention synergistically improves the softness of azelaic acid, thereby expanding the application of azelaic acid in soft hair products.

[0030] (3) From the perspective of environmental protection, the method for preparing supramolecular ionic salts of the present invention is green and environmentally friendly, avoiding the use and discharge of toxic and hazardous substances, and has a short reaction time, simple operation, and is easy to scale up for production.

[0031] (4) The preparation process of the supramolecular ionic salt of the present invention is very simple, green and safe, with low energy consumption and short time consumption. The obtained supramolecular ionic salt can be directly used as a raw material in the field of cosmetics or pharmacy without complicated post-processing such as purification and separation, and is suitable for industrial promotion. BRIEF DESCRIPTION OF THE DRAWINGS

[0032] Figure 1 It is the NMR spectrum of Formula I in Example 1.

[0033] Figure 2 It is the NMR spectrum of Formula II in Example 2. DETAILED DESCRIPTION

[0034] The preferred embodiments of the present invention are described below. It should be understood that the embodiments are for better explaining the present invention and are not used to limit the present invention.

[0035] Test method:

[0036] 1. Nuclear magnetic data test:

[0037] Machine specifications: AVANCEⅢHD 400MHz;

[0038] Machine manufacturer: Swiss Bruker Company;

[0039] Experimental parameters: magnet: 9.4 Tesla, magnetic field drift ≤ 8 Hz / h; probe width 5 mm, sampling frequency 400 MHz, test temperature 25 °C.

[0040] 2. Antibacterial performance test:

[0041] The antibacterial test includes the preparation of culture medium and experimental bacterial solution. The preparation of culture medium refers to the "Evaluation of Antimicrobial Protection of Cosmetics in Cosmetic Microbiology". The preparation of experimental bacterial solution includes: inoculating standard bacterial strains on culture medium for amplification, incubating the bacterial strains at 36°C for 24 hours, and then adding them to the corresponding concentration of elution solution for elution. The colorimetric turbidimetric method is used to prepare a liquid containing about 10 viable bacteria per 1mL. 8 The cell suspension of standard bacteria is used, and the number of bacteria in each 1mL of the cell suspension of standard bacteria is determined by the microbial limit test method. After the appropriate colonies are cultured, a 28-day microbial challenge test with one-time addition of bacteria is carried out. The test samples are divided into two groups, and 30g of experimental group solution and 30g of control group solution are added respectively. Add 1 portion of the test bacterial solution (0.5mL) to each test sample, mix it thoroughly, take samples every 7, 14, and 28 days, determine the bacterial content of the sample, and take its logarithmic value for evaluation. The conditions for the sample to pass the antimicrobial challenge test are: the logarithmic value of the bacterial count at 14 days decreases by no less than 2.0, and the bacterial count from 14 to 28 days does not increase; otherwise, it is considered to have failed.

[0042] 3. Hair combing test:

[0043] Take the Slightly Damaged Chinese hair sample for pretreatment: use 1% K12 (sodium dodecyl sulfate) solution in a constant temperature water bath at 37°C for 30 minutes, rinse with tap water at 37°C and 4.8L / min for 1 minute, use a lint-free paper towel to dry the water, hang it in a constant temperature and humidity environment for 12 to 24 hours to dry naturally; measure the dry combing work, which is the basic value before sampling.

[0044] Then, a new shampoo (test group) was obtained by machine washing hair using common commercial shampoo (control group) and adding 0.5% (mass percentage) of the supramolecular ion salt obtained in this example to the same commercial shampoo.

[0045] The hair was washed 15 times in a row without drying in the middle. The dry combing work of the hair bundles was measured for the 1st, 5th, 10th and 15th times respectively. The change rate of the test index before and after each hair bundle was washed was calculated according to formula (1):

[0046] K = (F after sample application / F before sample application - 1) × 100% (1)

[0047] If the combing work change rate K before and after the hair piece is subjected to the sample is less than 0, it means that the test sample has the effect of improving the combing property of the hair; if the combing work change rate K before and after the sample is greater than 0, that is, the combing work increases, it means that the test sample does not have the effect of improving the combing property of the hair.

[0048] 4. High and low temperature cycle:

[0049] Freeze at -5°C, take out and dissolve at 40°C. This is a cycle. Observe whether a uniform, transparent and stable solution can be formed.

[0050] Example 1

[0051] A supramolecular ionic salt of azelaic acid organosilicon, the structure of which is as follows:

[0052]

[0053] The preparation method of azelaic acid organosilicon supramolecular ion salt comprises the following steps:

[0054] 0.01 mol of azelaic acid and 0.02 mol of γ-aminopropyltriethoxysilane were weighed and put into a reaction container, and stirred at 25° C., 500 rpm, and natural air atmosphere for 40 min to obtain a uniform, transparent and stable liquid supramolecular ion salt.

[0055] The synthetic route is as follows:

[0056]

[0057] The content of azelaic acid in the obtained supramolecular ion salt is 30wt%. It is diluted 1 times, 5 times, 10 times, 20 times and 50 times with water. The obtained supramolecular ion salt and the diluted systems are placed in natural light at room temperature for 3 months, in an oven at 45°C for 3 months, and cycled at high and low temperatures (-5 to 40°C) for 15 times. There is no precipitation of insoluble matter and no color change.

[0058] The H NMR spectrum of supramolecular ion salts is as follows Figure 1 As shown;

[0059] The H NMR spectrum data of supramolecular ion salt are as follows:

[0060] 1H NMR (400MHz, DMSO) δ5.64(s,6H),3.79-3.69(m,6H),3.47-3.41(m,6H),2.70-2.52(m,4H),2.08-1.98(m,6 H),1.53-1.41(m,6H),1.33-1.18(m,6H),1.15(t,J=7.0Hz,9H),1.06(t,J=7.0Hz,9H),0.68-0.44(m,4H).

[0061] from Figure 1 It can be seen that: azelaic acid has an obvious carboxyl proton peak at the chemical shift of 11.93ppm; at the same time, in the nuclear magnetic hydrogen spectrum of γ-aminopropyltriethoxysilane, the amino hydrogen is an active hydrogen with a peak position of about 1.47ppm, and the total number of hydrogens is 2. Compared with azelaic acid and γ-aminopropyltriethoxysilane, the carboxyl proton hydrogen signal of the supramolecular ion salt at the hydrogen chemical shift of 11.93ppm disappears, and a new single broad peak appears at the chemical shift of 5.64ppm with a total number of hydrogens of 6, which is the 6 protonated amino (+NH3) hydrogen peaks in the supramolecular ion salt. This clearly shows that the carboxyl proton of azelaic acid has migrated to the amino group of γ-aminopropyltriethoxysilane, realizing the interaction between molecules. In addition, the number of hydrogens (62 H) in the H NMR spectrum of the supramolecular ion salt is completely consistent with the structure of Formula I. In addition to the above-mentioned proton migration, other hydrogens have partial chemical shift shifts compared to the monomers of azelaic acid and γ-aminopropyltriethoxysilane. These all indicate that the chemical environment in the obtained supramolecular ion salt has changed relative to the two independent monomer molecules, that is, azelaic acid as a hydrogen bond donor and γ-aminopropyltriethoxysilane as a hydrogen bond acceptor form a supramolecular ion salt through intermolecular proton transfer.

[0062] Triple distilled water was added to the supramolecular ion salt obtained in Example 1 to prepare a sample with a nonanedioic acid concentration of 0.5 mol / L as the experimental group; 0.05 mol of nonanedioic acid and 0.05 mol of sodium hydroxide were weighed, added to 100 mL of triple distilled water, heated to dissolve, and after dissolution, the pH of the solution was adjusted to 7.0 with 1 mol / L hydrochloric acid, and the solution after filtration and sterilization was used as a blank control for antibacterial test, recorded as control group 1; a 1 mol / L triple distilled aqueous solution of γ-aminopropyltriethoxysilane was prepared as control group 2 for antibacterial test.

[0063] The test results are shown in Table 1. It can be seen from Table 1 that the number index of Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus in the experimental group and the control group 1 decreased by more than 2.0 on the 14th day, and the number index of the control group 2 decreased relatively little on the 14th day; the number of bacteria in all components did not increase from 14 to 28 days, and all three components passed the antibacterial challenge test. Compared with the monomers of azelaic acid and γ-aminopropyltriethoxysilane, the addition of the supramolecular ion salt system sample of this embodiment has an enhanced sterilization effect on Escherichia coli and Staphylococcus aureus on the 7th day, indicating that the supramolecular ion salt formed by azelaic acid and γ-aminopropyltriethoxysilane has better antibacterial properties than the single molecules of azelaic acid and γ-aminopropyltriethoxysilane themselves, that is, the combination of the two has a synergistic effect on antibacterial properties.

[0064] Table 1

[0065]

[0066] Note: The data after the slash are the data of control group 2.

[0067] Table 2

[0068]

[0069] The results of the hair combing test are shown in Table 2. It can be seen from Table 2 that after the hair bundles were treated with the shampoo (test group) containing 0.5% of the supramolecular ion salt obtained in this embodiment for multiple times, the average combing work value of the hair bundles after treatment was 0.293 J, and the average K value was -62.045%. The average combing work value of the hair bundles treated with ordinary commercially available shampoo in the control group was 0.306 J, and the average K value was -55.95%. The average K value of the experimental group was reduced more, indicating that the experimental group improved the hair combing performance more excellently as a whole; and after 15 times of sampling, the K value of the experimental group was -46.89%, while the K value of the control group was only -30.45%, indicating that the experimental group also performed better in improving the long-term stability of hair combing. The experiment shows that the supramolecular ion salt obtained in this embodiment can effectively reduce the hair combing work and improve the hair combing performance.

[0070] Example 2

[0071] A supramolecular ionic salt of azelaic acid organosilicon, the structure of which is as follows:

[0072]

[0073] The preparation method comprises the following steps:

[0074] Weigh 0.01 mol of azelaic acid and 0.01 mol of γ-aminopropyltriethoxysilane and put them into a reaction container; the reaction atmosphere is nitrogen, and ultrasonic treatment is performed at 80° C. for 5 minutes to obtain a uniform, transparent and stable liquid supramolecular ion salt.

[0075] The synthetic route is as follows:

[0076]

[0077] The content of azelaic acid in the obtained supramolecular ion salt is 46wt%. It is diluted with water 1 times, 5 times, 10 times, 20 times and 50 times. The obtained supramolecular ion salt and the diluted systems are placed in natural light at room temperature for 3 months, in an oven at 45°C for 3 months, and cycled at high and low temperatures (-5 to 40°C) for 15 times. There is no precipitation of insoluble matter and no color change.

[0078] The nuclear magnetic resonance proton spectra of azelaic acid, γ-aminopropyltriethoxysilane, and supramolecular ion salts are as follows Figure 2 As shown:

[0079] The H NMR spectrum data of supramolecular ion salt are as follows:

[0080] 1 H NMR(400MHz, CDCl3)δ4.51(s,4H),3.98-3.58(m,6H),2.94-2.77(m,2H),2.29-2.15(m,4H),1.90-1.67 (m,2H),1.64-1.49(m,4H),1.44-1.30(m,4H),1.26-1.19(m,9H),0.9-0.79(m,2H),0.73-0.53(m,2H).

[0081] from Figure 2It can be seen that: azelaic acid has an obvious carboxyl proton peak at the chemical shift of 11.93ppm; at the same time, in the nuclear magnetic hydrogen spectrum of γ-aminopropyltriethoxysilane, the amino hydrogen is an active hydrogen with a peak position of about 1.47ppm, and the total number of hydrogens is 2. Compared with azelaic acid and γ-aminopropyltriethoxysilane, the carboxyl proton hydrogen signal of the supramolecular ion salt at the hydrogen chemical shift of 11.93ppm disappears, and a new peak appears at the chemical shift of 4.51ppm with a total number of hydrogens of 4, which is the peak of 3 protonated amino groups (+NH3) in the supramolecular ion salt, and the remaining 1 carboxyl active H also peaks at this position. This clearly shows that the carboxyl proton of azelaic acid has migrated to the amino group of γ-aminopropyltriethoxysilane, realizing the interaction between molecules. At the same time, the remaining carboxyl proton and the protonated amino group are at the same position, which indicates that in the supramolecular ion salt, the hydroxyl group, the amino proton and the carboxyl proton are in a dynamic exchange state in the deuterated reagent, which further indicates that azelaic acid and γ-aminopropyltriethoxysilane form supramolecular ion salts through supramolecular action. In addition, the number of hydrogens (39 H) in the nuclear magnetic hydrogen spectrum of the supramolecular ion salt is consistent with the structure of formula II. In addition to the above-mentioned proton migration (+NH3), other hydrogens have partial chemical shift shifts compared to azelaic acid and γ-aminopropyltriethoxysilane monomers. These all indicate that the chemical environment in the obtained supramolecular ion salt has changed relative to the two independent monomer molecules, that is, azelaic acid as a hydrogen bond donor and γ-aminopropyltriethoxysilane as a hydrogen bond acceptor form supramolecular ion salts through intermolecular proton transfer.

[0082] In order to further illustrate the stability of the supramolecular ion salt obtained in the present invention in the hair formula system, the supramolecular ion salt obtained in this example is made into a hair care essence according to the formula in Table 3 below:

[0083] Table 3 Hair Care Essence Formula

[0084]

[0085] Note: Centella asiatica extract was purchased from Guilin Newtech Biotechnology Co., Ltd.

[0086] The preparation method of hair care essence is as follows:

[0087] Add ingredients No. 1 to 5, No. 7 and No. 8 into the main cup and dissolve evenly, then heat to 75°C;

[0088] Add ingredients 6 and 11 into the main cup and stir well;

[0089] Add ingredient No. 9 into the main cup and mix evenly;

[0090] Cool down to 45°C, add raw materials No. 10 and No. 12, stir evenly, and complete the preparation of hair care essence.

[0091] The hair care essence has passed the stability test according to GB / T 26367-2010 standard and the stability is qualified.

[0092] Comparative Example 1

[0093] The γ-aminopropyltriethoxysilane in Example 1 was adjusted to polydimethylsiloxane alcohol (viscosity 10000 cst), and the other ingredients were kept the same as in Example 1.

[0094] The results showed that: a stable liquid system could not be formed, and the obtained system was a solid-liquid mixture; the obtained solid-liquid mixture was not miscible when diluted with water 1 times, 5 times, 10 times, 20 times, and 50 times, and there were solid insolubles.

[0095] Comparative Example 2

[0096] The γ-aminopropyltriethoxysilane in Example 1 was adjusted to serine, and the rest was the same as in Example 1.

[0097] The results showed that: a stable liquid system could not be formed, and the obtained system was a solid-liquid mixture; the obtained solid-liquid mixture was not miscible when diluted with water 1 times, 5 times, 10 times, 20 times, and 50 times, and there were solid insolubles.

[0098] Comparative Example 3

[0099] The γ-aminopropyltriethoxysilane in Example 1 was adjusted to triethoxyoctylsilane, and the rest was the same as in Example 1.

[0100] The results showed that: a stable liquid system could not be formed, and the obtained system was a solid-liquid mixture; the obtained solid-liquid mixture was not miscible when diluted with water 1 times, 5 times, 10 times, 20 times, and 50 times, and there were solid insolubles.

[0101] Comparative Example 4

[0102] The γ-aminopropyltriethoxysilane in Example 1 was adjusted to aminopropylpolydimethylsiloxane, and the rest was the same as in Example 1.

[0103] The results showed that: a stable liquid system could not be formed, and the obtained system was a solid-liquid mixture; the obtained solid-liquid mixture was not miscible when diluted with water 1 times, 5 times, 10 times, 20 times, and 50 times, and there were solid insolubles.

[0104] Comparative Example 5

[0105] The γ-aminopropyltriethoxysilane in Example 1 was adjusted to capsaicin, and the rest was the same as Example 1.

[0106] The results showed that: a stable liquid system could not be formed, and the obtained system was a solid powder; the obtained solid powder was not miscible when diluted with water 1 times, 5 times, 10 times, 20 times, and 50 times, and there were solid insolubles.

[0107] Comparative Example 6

[0108] A rhododendron acid capsaicin ion salt is prepared by the following method:

[0109] In a nitrogen atmosphere and a warm water bath at 40°C, capsaicin is added to an aqueous solution containing azelaic acid (0.5 mol / L) for neutralization reaction to obtain the azelaic acid capsaicin ionic salt; the molar ratio of azelaic acid to capsaicin is 1:2; the neutralization reaction time is 12 hours; the obtained mixed solution is separated and purified by recrystallization, and the recrystallized product is filtered and dried to obtain the azelaic acid capsaicin ionic salt finished product; the drying temperature is 50°C and the time is 48 hours. This scheme is time-consuming and requires the use of organic solvents to recrystallize the ionic salt, requiring a large amount of post-processing operations such as purification. The obtained ionic salt is not miscible when diluted with water 1 times, 5 times, 10 times, 20 times, and 50 times, and there are a large number of solid insolubles.

[0110] The hair combing test results of the comparative example are shown in Table 4:

[0111] Table 4

[0112]

[0113] It can be seen from Table 4 that after the hair bundles were treated with the shampoo (experimental group) containing 0.5% of the product obtained in this comparative example for multiple times, the average combing work value of the hair bundles after treatment was 0.3225 J, and the average K value was -53.73%. The average combing work value of the hair bundles treated with ordinary commercially available shampoo in the control group was 0.306 J, and the average K value was -55.95%. The average K value of the experimental group was similar to or even slightly lower than that of the control group, and the degree of reduction of the K value after 15 times of treatment was also similar, indicating that whether the product of this comparative example is added has little effect on the combing effect of the shampoo, that is, the product obtained in this comparative example does not have a significant effect on improving the combing properties of hair.

[0114] Although the present invention has been disclosed as above in the form of a preferred embodiment, it is not intended to limit the present invention. Anyone familiar with this technology can make various changes and modifications without departing from the spirit and scope of the present invention. Therefore, the scope of protection of the present invention should be based on the definition of the claims.

Claims

1. A method for improving the smoothness of hair, characterized in that: Azelaic acid organosilicon supramolecular ionic salt is used; The structural formula of the azelaic acid organosilicon supramolecular ion salt is as follows:

2. The method according to claim 1, characterized in that The preparation method of azelaic acid organosilicon supramolecular ion salt comprises the following steps: Azelaic acid and γ-aminopropyltriethoxysilane are mixed in a molar ratio of 1:1 or 1:2, and stirred and heated or subjected to constant temperature ultrasound to obtain the azelaic acid organosilicon supramolecular ion salt.

3. The method according to claim 2, characterized in that The atmosphere for stirring, heating or constant temperature ultrasound is nitrogen or natural air.

4. The method according to claim 2, characterized in that: The temperature of stirring heating or constant temperature ultrasound is 20 to 80°C.

5. The method according to claim 2, characterized in that: The time of stirring heating or constant temperature ultrasound is 5 to 40 minutes.

6. The method according to claim 2, characterized in that The rotation speed of stirring and heating is 200-1000rpm, and the power of constant temperature ultrasound is 200-800W.

7. A hair shampoo and hair care product with antibacterial and softening properties, characterized in that: Azelaic acid organosilicon supramolecular ionic salt is used; The structural formula of the azelaic acid organosilicon supramolecular ion salt is as follows:

8. The hair shampoo and hair care product with antibacterial and softening properties according to claim 7, characterized in that: The dosage of azelaic acid organosilicon supramolecular ion salt is 0.1 to 30 wt %.

Images