CN111773130A

CN111773130A - Hydroxypropyl tetrahydropyrane triol compound and preparation method and application thereof

Info

Publication number: CN111773130A
Application number: CN202010689302.XA
Authority: CN
Inventors: 宁继彬
Original assignee: Beileke Shanghai Biotechnology Co ltd
Current assignee: Beileke Shanghai Biotechnology Co ltd
Priority date: 2020-07-17
Filing date: 2020-07-17
Publication date: 2020-10-16

Abstract

The invention discloses a hydroxypropyl tetrahydropyrane triol compound and a preparation method and application thereof. The hydroxypropyl tetrahydropyrane triol compound comprises hydroxypropyl tetrahydropyrane triol, hyaluronic acid and/or salt thereof, hydrolyzed hyaluronic acid and/or salt thereof, chitosan (hyaluronic acid precursor), deionized water, and a component with a preservative effect or a preservative. The compound strengthens the connection between the skin epidermis and the dermis, thereby improving the expression and the content of fibroblasts in the dermis to extracellular matrixes such as collagen, proteoglycan and glycosaminoglycan, and improving the skin elasticity and the skin firmness to realize the anti-aging function of the skin. The hyaluronic acid and/or salt thereof, the hydrolyzed hyaluronic acid and/or salt thereof and the acetyl chitosamine (precursor of hyaluronic acid) are added into the compound taking the hydroxypropyl tetrahydropyrane triol as the main component according to a certain proportion, and the synergy of the components in the aspect of efficacy is fully exerted according to a proper proportion, so that the functions of moisturizing, anti-aging and the like of skin care are exerted to a greater extent.

Description

Hydroxypropyl tetrahydropyrane triol compound and preparation method and application thereof

Technical Field

The invention relates to the technical field of biology, and particularly relates to a hydroxypropyl tetrahydropyran triol compound, a preparation method and application thereof.

Background

In the cosmetic field, moisturizing and anti-aging are two main requirements of skin care, hyaluronic acid or a salt thereof is generally widely used as a film-forming humectant, and collagen is generally applied to related formulas due to the functions of moisturizing and improving skin elasticity.

In terms of the prior art, the care products currently available on the market cannot effectively and rapidly strengthen the connection between epidermis and dermis, and cannot significantly improve skin elasticity and skin firmness from the aspect of improving the expression and content of fibroblasts to extracellular matrixes such as collagen, proteoglycan and glycosaminoglycan so as to realize the function of resisting skin aging. In general, the components in the formula are added in a simple or random compatibility manner, or the components are used singly or in a compound manner in an unscientific quantitative ratio relationship, so that the synergy of the multiple functions and the effects of the components is difficult to be fully exerted. The invention discloses a multi-effect repair essence and a preparation process thereof in Chinese invention patent application document with publication number CN110302086A, wherein the multi-effect repair essence comprises hydrolyzed sodium hyaluronate, hydroxypropyl tetrahydropyrane triol and the like, but only relates to the compound synergistic action of the hydroxypropyl tetrahydropyrane triol, small molecule tripeptide and carboxymethyl beta-glucan sodium when being mixed for use, does not relate to the synergistic action of the hydroxypropyl tetrahydropyrane triol, hyaluronic acid and/or salt with different molecular weights and chitosan amine as a hyaluronic acid precursor, and does not mention the compound synergistic action, the quantity ratio relationship and the synergistic action of the hydroxypropyl tetrahydropyrane triol, the hyaluronic acid and/or salt, collagen and hydrolyzed collagen.

Disclosure of Invention

In order to overcome the defects of the prior art, the invention provides a hydroxypropyl tetrahydropyran triol compound and a preparation method and application thereof.

In order to realize the purpose of the invention, the technical scheme adopted by the invention is as follows:

according to one aspect of the present invention, there is provided a hydroxypropyl tetrahydropyran triol formulation comprising hydroxypropyl tetrahydropyran triol, hyaluronic acid and/or a salt thereof, hydrolyzed hyaluronic acid and/or a salt thereof, chitosamine (a precursor of hyaluronic acid), deionized water, an ingredient having a preservative effect or a preservative.

Further, the preservative is one or more of phenoxyethanol, ethylhexyl glycerol, methyl hydroxybenzoate, ethylparaben, propyl hydroxybenzoate, octanoyl ketone, octanoyl hydroxamic acid, benzyl alcohol, benzoic acid, benzalkonium chloride, imidazolidinyl urea, hydantoin and isothiazolinone, and the deionized water is purified water.

Further, the dihydric alcohol is any one or more of propylene glycol, pentanediol, hexanediol and butanediol.

Further, the salt of hyaluronic acid and the salt of hydrolyzed hyaluronic acid are any one or more of sodium salt, potassium salt, zinc salt and calcium salt.

Further, the hyaluronic acid and/or a salt thereof includes high molecular weight hyaluronic acid and/or a salt thereof, and low molecular weight hyaluronic acid and/or a salt thereof.

Further, the formulation also includes collagen and hydrolyzed collagen.

Furthermore, the molecular weight of the high molecular hyaluronic acid and/or the salt thereof is 70-220 ten thousand Da, the molecular weight of the low molecular hyaluronic acid and/or the salt thereof is 5-50 ten thousand Da, the molecular weight of the hydrolyzed hyaluronic acid and/or the salt thereof is 400-1 ten thousand Da, the molecular weight of the collagen is 2-8 ten thousand Da, and the molecular weight of the hydrolyzed collagen is 200-5000 Da.

Furthermore, the molecular weight of the high molecular hyaluronic acid and/or the salt thereof is 120-150 ten thousand Da, the molecular weight of the low molecular hyaluronic acid and/or the salt thereof is 10-40 ten thousand Da, the molecular weight of the hydrolyzed hyaluronic acid and/or the salt thereof is 400-1 ten thousand Da, the molecular weight of the collagen is 2-8 ten thousand Da, and the molecular weight of the hydrolyzed collagen is 200-5000 Da.

Further, the compound comprises the following components in percentage by mass: 1-50% of hydroxypropyl tetrahydropyrane triol, 0.05-0.8% of high molecular hyaluronic acid and/or salt thereof, 0.05-2% of low molecular hyaluronic acid and/or salt thereof, 0.05-2% of hydrolyzed hyaluronic acid and/or salt thereof, 0.05-0.5% of collagen, 0.05-2.0% of hydrolyzed collagen, 1.0-5.0% of chitosan, 5.0-10.0% of dihydric alcohol, 0-0.5% of p-hydroxyacetophenone and the balance of purified water, wherein the sum of the mass percentages of the components is 100%.

Further, the components are as follows according to the mass ratio: 5-20% of hydroxypropyl tetrahydropyrane triol, 0.1-0.5% of high molecular hyaluronic acid and/or salt thereof, 0.5-1.5% of low molecular hyaluronic acid and/or salt thereof, 0.1-0.5% of hydrolyzed hyaluronic acid and/or salt thereof, 0.05-0.5% of collagen, 0.05-2.0% of hydrolyzed collagen, 1.0-5.0% of chitosan, 5.0-10.0% of dihydric alcohol, 0-0.5% of p-hydroxyacetophenone, and the balance of purified water, wherein the sum of the mass percentages of the components is 100%.

According to another aspect of the present invention, there is provided a method for preparing the above-mentioned hydroxypropyl tetrahydropyran triol formulation, comprising the steps of:

s202: adding dihydric alcohol, hyaluronic acid and/or its salt, and low molecular hyaluronic acid and/or its salt into emulsifying tank, and thoroughly moistening and dispersing;

s204: adding deionized water, heating to 50-80 ℃, stirring to obtain a transparent uniform solution, and keeping the temperature for 10-60 minutes for later use;

s206: when the temperature is reduced to 30-50 ℃, adding the hydroxypropyl tetrahydropyrane triol complex, and fully stirring and dissolving to obtain a uniform solution;

s208: and after the temperature of the uniform solution is reduced to normal temperature, adding hydrolyzed hyaluronic acid and/or salt thereof, acetyl chitosamine, dihydric alcohol and/or p-hydroxyacetophenone and the balance of deionized water, and uniformly stirring until the hydrolyzed hyaluronic acid and/or salt thereof, the acetyl chitosamine, the dihydric alcohol and/or the p-hydroxyacetophenone and the balance of deionized water are completely dissolved, thereby obtaining the hydroxypropyl tetrahydropyrane triol compound.

Further, the preparation method of the hydroxypropyl tetrahydropyrane triol compound comprises the following steps:

s207: adding collagen and hydrolyzed collagen into the homogeneous solution obtained in the step S206, and fully stirring and dissolving the mixture to obtain a homogeneous solution;

According to a further aspect of the present invention, there is provided a cosmetic comprising the above hydroxypropyl tetrahydropyran triol formulation.

Furthermore, the mass content of the hydroxypropyl tetrahydropyrane triol compound in the cosmetic is 0.1-20%.

Further, the cosmetic also comprises one or more of alpha-arbutin, nicotinamide, ceramide, vitamin C and its derivatives, allantoin, glycyrrhizic acid, betaine, small molecule peptides, plant extract, and fubotine.

According to a further aspect of the present invention there is provided the use of a hydroxypropyl tetrahydropyran triol formulation in the preparation of a facial care, hand care, body care, head care, nail care, mouth care and lip care product.

According to the technical scheme, the compound containing the hydroxypropyl tetrahydropyrane triol promotes the skin to maintain the integrity of an extracellular matrix (ECM) and strengthens the connection between the skin epidermis and the dermis, so that the expression of fibroblasts in an extracellular matrix on collagen, proteoglycan and glycosaminoglycan is promoted, the content of the collagen, the proteoglycan and the glycosaminoglycan is increased, the skin elasticity is improved, the skin compactness is increased, and the function of delaying the skin aging is realized.

Furthermore, through the compound taking the hydroxypropyl tetrahydropyrane triol as the main component and other components with lower dosage, such as high molecular weight hyaluronic acid and/or salt thereof, low molecular weight hyaluronic acid and/or salt thereof, hydrolyzed hyaluronic acid and/or salt thereof, acetylated chitosamine (hyaluronic acid precursor), collagen, hydrolyzed collagen and the like, the synergy of the components in the aspect of efficacy is exerted, and the functions of moisturizing, anti-aging and the like of skin care are exerted to a greater extent.

In summary, compared with the prior art, the invention has at least one of the following beneficial effects:

1. the hydroxypropyl tetrahydropyrane triol compound can improve the expression and content of fibroblasts in a dermis layer to extracellular matrixes such as collagen, proteoglycan and glycosaminoglycan, promote the skin to maintain the integrity of an extracellular matrix (ECM) of the skin, and can effectively strengthen the connection between the skin epidermis and the dermis, thereby obviously improving the skin elasticity and the skin firmness to realize the anti-aging function of the skin.

2. The cosmetic uses the hydroxypropyl tetrahydropyrane triol as a main component and is scientifically compatible with other multifunctional components, such as one or more of high molecular hyaluronic acid or salt thereof, low molecular hyaluronic acid or salt thereof, hydrolyzed hyaluronic acid or salt thereof, chitosan, collagen or hydrolyzed collagen, so that a synergistic effect is generated, and the skin care effects of moisturizing and resisting aging of the product are improved.

3. When the hydroxypropyl tetrahydropyrane triol compound is prepared from the components according to a proper mass ratio, particularly the compound of hyaluronic acid and/or salt with different molecular weights and the hyaluronic acid precursor, namely the acetyl chitosamine, can show better synergistic skin care effect, so that the cosmetics have comprehensive and positive moisturizing and anti-aging effects.

It is to be understood that within the scope of the present invention, the above-described features of the present invention and those specifically described below, such as in the examples, may be combined with each other to form new or preferred embodiments. Not to be reiterated herein, but to the extent of space.

Detailed Description

The present invention will be described in detail with reference to examples.

According to an exemplary embodiment of the present invention, a hydroxypropyl tetrahydropyran triol formulation is provided, the formulation comprising hydroxypropyl tetrahydropyran triol, hyaluronic acid and/or a salt thereof, hydrolyzed hyaluronic acid and/or a salt thereof, chitosamine (a precursor of hyaluronic acid), a preservative or preservative agent, and deionized water.

According to the technical scheme, the compound containing the hydroxypropyl tetrahydropyrane triol promotes the skin to maintain the integrity of an extracellular matrix (ECM) and strengthens the connection between the skin epidermis and the dermis, so that the expression and content of fibroblasts in the dermis layer to extracellular matrixes such as collagen, proteoglycan and glycosaminoglycan are improved, and the skin elasticity and the skin firmness are improved to realize the anti-aging function of the skin. The acetyl chitosamine is a precursor of hyaluronic acid, is beneficial to the synthesis of hyaluronic acid in skin, regulates the metabolism of keratinocytes and improves skin color; the hyaluronic acid or its salt has good moisture keeping, film forming, skin nourishing, and cutin softening effects, and the hydrolyzed hyaluronic acid or its salt has skin repairing, antioxidant, and skin relieving effects. The inventor finds that when hyaluronic acid and/or salt thereof, hydrolyzed hyaluronic acid and/or salt thereof and chitosan, namely hyaluronic acid precursor, are added into a compound taking hydroxypropyl tetrahydropyrane triol as a main component in a certain proportion, the compound not only can fully exert the effects of multifunctional moisturizing, anti-aging, anti-oxidation and skin nourishing of each component while strengthening the connection between the skin epidermis and the dermis, but also can generate the synergistic effect of the effects of each component, and has better effect than the effect when a single component is used or the components are simply compounded.

In another preferred embodiment, the component with antiseptic effect is dihydric alcohol and/or p-hydroxyacetophenone, the antiseptic is one or more of phenoxyethanol, methyl hydroxybenzoate and benzyl alcohol, and the deionized water is purified water.

In the above technical scheme, the deionized water may be purified water. The antiseptic system can be constructed by dihydric alcohol, p-hydroxyacetophenone, dihydric alcohol and p-hydroxyacetophenone. According to the technical scheme, other preservatives can be used for completely or partially replacing dihydric alcohol and/or p-hydroxyacetophenone, for example, one or more of phenoxyethanol, ethylhexyl glycerol, methyl hydroxybenzoate, ethylparaben, propyl hydroxybenzoate, octanoyl ketone, octanoyl hydroxamic acid, benzyl alcohol, benzoic acid, benzalkonium chloride, imidazolidinyl urea, hydantoin, isothiazolinone and the like are selected to construct a preservative system, and the dihydric alcohol and/or the p-hydroxyacetophenone are completely or partially replaced.

In another preferred embodiment, the dihydric alcohol is any one or more of propylene glycol, pentylene glycol, hexylene glycol, butylene glycol.

In the above technical solution, the dihydric alcohol may be any one or more of propylene glycol, pentylene glycol, hexylene glycol, and butylene glycol. For example, the preservative system can adopt hexanediol, pentanediol and p-hydroxyacetophenone, or adopt hexanediol, pentanediol or p-hydroxyacetophenone, and also can adopt one or two, three, four or all of propylene glycol, pentanediol, hexanediol, butanediol and p-hydroxyacetophenone.

In another preferred embodiment, the salt of hyaluronic acid and the salt of hydrolyzed hyaluronic acid is any one or more of sodium salt, potassium salt, zinc salt, calcium salt. That is, the high molecular weight hyaluronic acid and/or salt thereof, the low molecular weight hyaluronic acid and/or salt thereof, and the hydrolyzed hyaluronic acid and/or salt thereof may be selected from any one or more of sodium salt, potassium salt, zinc salt, and calcium salt. For example, but not limited to, any one or more of sodium hyaluronate, potassium hyaluronate, zinc hyaluronate, calcium hyaluronate, hydrolyzed sodium hyaluronate, hydrolyzed potassium hyaluronate, hydrolyzed zinc hyaluronate, and hydrolyzed calcium hyaluronate.

In another preferred embodiment, the hyaluronic acid and/or salt thereof comprises high molecular weight hyaluronic acid and/or salt thereof, low molecular weight hyaluronic acid and/or salt thereof.

In the technical scheme, the high molecular hyaluronic acid or the salt thereof has good moisture retention and film forming properties, the low molecular hyaluronic acid or the salt thereof has the effects of nourishing skin and softening cutin, and the hydrolyzed hyaluronic acid or the salt thereof has good functions of repairing, resisting oxidation and relieving skin. In the present embodiment, by adding high molecular weight hyaluronic acid and/or a salt thereof, low molecular weight hyaluronic acid and/or a salt thereof, and using hyaluronic acid and/or a salt thereof of different molecular weights, the multi-functional effects of each component are sufficiently exerted while strengthening the connection between the epidermis and the dermis of the skin, and a synergistic effect of the effects of each component is produced, which produces better repairing, antioxidant and soothing effects than those obtained by using hydroxypropyl tetrahydropyranetriol and hyaluronic acid and/or a salt thereof alone, or better repairing, antioxidant and soothing effects than those obtained by simply using hydroxypropyl tetrahydropyranetriol, hyaluronic acid and/or a salt thereof in combination and hydrolyzing hyaluronic acid and/or a salt thereof.

In another preferred embodiment, the formulation further comprises collagen and hydrolyzed collagen.

In the technical scheme, the collagen and the hydrolyzed collagen are beneficial to maintaining extracellular matrix in the dermis layer, so that the skin care effect is achieved. Adding a certain proportion of collagen with lower content and hydrolyzed collagen into the hydroxypropyl tetrahydropyrane triol compound, the multifunctional moisturizing, anti-aging, anti-oxidation and skin nourishing effects of the skin care product are fully exerted while the connection between the epidermis and the dermis of the skin is strengthened, the synergistic effect of the effects of all the components is generated, and the multifunctional moisturizing, anti-aging, anti-oxidation and skin nourishing effects are better than those of the skin care product which uses hydroxypropyl tetrahydropyrane triol, hyaluronic acid and/or salt thereof, hydrolyzed hyaluronic acid and/or salt thereof, collagen and hydrolyzed collagen as single components, or produces more excellent multifunctional moisturizing, anti-aging, anti-oxidation and skin-nourishing effects than when simply compounding hydroxypropyl tetrahydropyrane triol, hyaluronic acid and/or a salt thereof, hydrolyzed hyaluronic acid and/or a salt thereof, chitosamine (a precursor of hyaluronic acid), collagen and hydrolyzed collagen.

In another preferred embodiment, the molecular weight of the high molecular weight hyaluronic acid and/or salt thereof is 70-220 ten thousand Da, the molecular weight of the low molecular weight hyaluronic acid and/or salt thereof is 5-50 ten thousand Da, the molecular weight of the hydrolyzed hyaluronic acid and/or salt thereof is 400-1 ten thousand Da, the molecular weight of the collagen is 2-8 ten thousand Da, and the molecular weight of the hydrolyzed collagen is 200-5000 Da.

Repeated research and experiments by the inventor show that the hydroxypropyl tetrahydropyrane triol and the hyaluronic acid and/or the salt thereof with the molecular weight have better synergistic effect after being compounded, and simultaneously, the addition of the collagen and the hydrolyzed collagen with the preferred molecular weight further enhances the activity of the synergistic effect of the compound, and expands the application of the hydroxypropyl tetrahydropyrane triol compound in the formula of the skin care product.

In another preferred embodiment, the molecular weight of the high molecular weight hyaluronic acid and/or salt thereof is 120-150 ten thousand Da, the molecular weight of the low molecular weight hyaluronic acid and/or salt thereof is 10-40 ten thousand Da, the molecular weight of the hydrolyzed hyaluronic acid and/or salt thereof is 400-1 ten thousand Da, the molecular weight of the collagen is 2-8 ten thousand Da, and the molecular weight of the hydrolyzed collagen is 200-5000 Da.

In the technical scheme, the molecular weight of each component is optimized, such as the molecular weight of high molecular hyaluronic acid and/or salt thereof is 70-220 ten thousand Da, the molecular weight of low molecular hyaluronic acid and/or salt thereof is 5-50 ten thousand Da, the molecular weight of hydrolyzed hyaluronic acid and/or salt thereof is 400-1 ten thousand Da, the molecular weight of collagen is 2-8 ten thousand Da, and the molecular weight of hydrolyzed collagen is 200-5000Da, so that the synergy of each component in the aspect of efficacy is improved, and the efficacy of the compound on skin care is exerted to the maximum extent.

In another preferred embodiment, the components are as follows according to mass ratio: the components are as follows according to mass ratio: 1-50% of hydroxypropyl tetrahydropyrane triol, 0.05-0.8% of high molecular hyaluronic acid and/or salt thereof, 0.05-2% of low molecular hyaluronic acid and/or salt thereof, 0.05-2% of hydrolyzed hyaluronic acid and/or salt thereof, 0.05-0.5% of collagen, 0.05-2.0% of hydrolyzed collagen, 1.0-5.0% of chitosan, 5.0-10.0% of dihydric alcohol, 0-0.5% of p-hydroxyacetophenone and the balance of purified water, wherein the sum of the mass percentages of the components is 100%.

The inventor finds that in the formula of the hydroxypropyl tetrahydropyrane triol compound, various moisturizing components are simply or randomly added in a compatible manner, or are used singly or in a compound manner, the scientific quantitative relation is not used, so that the multifunctional effects of the components are difficult to fully play. Therefore, through repeated research and experiments, the inventor finds that the formula adopts the following components in percentage by mass: 1-50% of hydroxypropyl tetrahydropyran triol, 0.05-0.8% of high molecular hyaluronic acid and/or salt thereof, 0.05-2% of low molecular hyaluronic acid and/or salt thereof, 0.05-2% of hydrolyzed hyaluronic acid and/or salt thereof, 0.05-0.5% of collagen, 0.05-2.0% of hydrolyzed collagen, 1.0-5.0% of chitosan, 5.0-10.0% of dihydric alcohol, 0-0.5% of p-hydroxyacetophenone and the balance of purified water, wherein the sum of the mass percentages of the components is 100%, the optimal synergistic effect of the components can be generated, and the obtained hydroxypropyl tetrahydropyran triol compound has the best effects of moisture retention, aging resistance and oxidation resistance.

In another preferred embodiment, the components are as follows according to mass ratio: 5-20% of hydroxypropyl tetrahydropyrane triol, 0.1-0.5% of high molecular hyaluronic acid and/or salt thereof, 0.5-1.5% of low molecular hyaluronic acid and/or salt thereof, 0.1-0.5% of hydrolyzed hyaluronic acid and/or salt thereof, 0.05-0.5% of collagen, 0.05-2.0% of hydrolyzed collagen, 1.0-5.0% of chitosan, 5.0-10.0% of dihydric alcohol, 0-0.5% of p-hydroxyacetophenone, and the balance of purified water, wherein the sum of the mass percentages of the components is 100%.

According to a typical embodiment of the invention, a preparation method of a hydroxypropyl tetrahydropyran triol compound is provided, wherein the hydroxypropyl tetrahydropyran triol compound prepared by the method comprises the following components in percentage by mass: 5.0-10.0% of hydroxypropyl tetrahydropyrane triol, 5-10% of dihydric alcohol, 0.2-0.4% of p-hydroxyacetophenone and 81-88% of deionized water, wherein the preparation method comprises the following steps:

s101: preparing 5.0-10.0% hydroxypropyl tetrahydropyrane triol compound solution in an emulsification tank;

s102: stirring the hydroxypropyl tetrahydropyrane triol compound solution, adding 5-10% of dihydric alcohol, 0.2-0.4% of p-hydroxyacetophenone and 81-88% of deionized water,

thus obtaining the 5.0-10.0% hydroxypropyl tetrahydropyrane triol compound A.

According to a typical embodiment of the invention, a preparation method of a hydroxypropyl tetrahydropyran triol compound is provided, wherein the hydroxypropyl tetrahydropyran triol compound prepared by the method comprises the following components in percentage by mass: 5.0-10.0% of hydroxypropyl tetrahydropyrane triol, 0.1-0.5% of high molecular sodium hyaluronate, 0.5-1.0% of low molecular sodium hyaluronate, 0.1-0.5% of hydrolyzed sodium hyaluronate, 1.0-5.0% of acetyl chitosamine, 0.2-0.4% of p-hydroxyacetophenone, 2.6-5% of propylene glycol, 0.4-1% of hexanediol, 2-4% of pentanediol and the balance of deionized water, wherein the sum of the mass percentages of the above components is 100%, and the preparation method comprises the following steps:

s202: adding 2.6-5% of propylene glycol, 0.1-0.5% of high molecular sodium hyaluronate and 0.5-1.0% of low molecular sodium hyaluronate into an emulsifying tank, and fully wetting and dispersing;

s204: adding 73-85% of the rest deionized water, heating to 50-80 ℃, stirring to obtain a transparent uniform solution, and keeping the temperature for 10-60 minutes for later use;

s206: when the temperature is reduced to 30-50 ℃, adding 5.0-10.0% of hydroxypropyl tetrahydropyrane triol compound, and fully stirring and dissolving to obtain a uniform solution;

s208: and after the temperature of the uniform solution is reduced to normal temperature, adding 0.1-0.5% of hydrolyzed sodium hyaluronate, 1.0-5.0% of acetyl chitosamine, 0.2-0.4% of p-hydroxyacetophenone, 0.4-1% of hexanediol and 2-4% of pentanediol, and uniformly stirring until the materials are completely dissolved, thereby obtaining the hydroxypropyl tetrahydropyrane triol compound B.

According to a typical embodiment of the invention, a preparation method of a hydroxypropyl tetrahydropyran triol compound is provided, wherein the hydroxypropyl tetrahydropyran triol compound prepared by the method comprises the following components in percentage by mass: 5.0-10.0% of hydroxypropyl tetrahydropyrane triol, 0.1-0.5% of high molecular sodium hyaluronate, 0.5-1.0% of low molecular sodium hyaluronate, 0.1-0.5% of hydrolyzed sodium hyaluronate, 1.0-5.0% of acetyl chitosamine, 0.1-0.5% of collagen, 0.5-2.0% of hydrolyzed collagen, 0.2-0.4% of p-hydroxyacetophenone, 2.6-5% of propylene glycol, 0.4-1% of hexanediol, 2-4% of pentanediol and the balance of deionized water, wherein the sum of the mass percentages of the above components is 100%, and the preparation method comprises the following steps:

s207: adding 0.1-0.5% of collagen and 0.5-2.0% of hydrolyzed collagen into the uniform solution, and fully stirring and dissolving to obtain the uniform solution;

s208: and after the temperature of the uniform solution is reduced to normal temperature, adding 0.1-0.5% of hydrolyzed sodium hyaluronate, 1.0-5.0% of acetyl chitosamine, 0.2-0.4% of p-hydroxyacetophenone, 0.4-1% of hexanediol and 2-4% of pentanediol, and uniformly stirring until the materials are completely dissolved, thereby obtaining the hydroxypropyl tetrahydropyrane triol compound C.

The ranges of the basic parameters of the hydroxypropyl tetrahydropyran triol formulation a, the hydroxypropyl tetrahydropyran triol formulation B and the hydroxypropyl tetrahydropyran triol formulation C obtained in the above embodiment are as follows:

according to an exemplary embodiment of the present invention, there is provided a cosmetic comprising the above-described hydroxypropyl tetrahydropyran triol formulation.

The cosmetic provided by the embodiment of the invention contains the hydroxypropyl tetrahydropyrane triol compound provided by the technical scheme of the invention, and the dosage form can be a solid dosage form, a semisolid dosage form, a liquid dosage form or an aerosol dosage form, such as a solution, a gel, a cream, an emulsion, an ointment, a cream, a paste, a cake, a powder, a patch, a spray product and the like. The cosmetic in the embodiment can improve the activity of fibroblasts in a cell experiment, promote the synthesis of hyaluronic acid in the fibroblasts, improve the expression of type I collagen, up-regulate the expression level of elastin, and has the effects of moisturizing and increasing skin elasticity.

According to a typical embodiment of the invention, the mass content of the hydroxypropyl tetrahydropyran triol compound in the cosmetic formula is 0.1-20%.

The cosmetic provided by the embodiment of the invention contains 0.1-20% of the hydroxypropyl tetrahydropyrane triol compound according to the technical scheme of the invention, and can be used for preparing a solid dosage form, a semisolid dosage form, a liquid dosage form or an aerosol dosage form which is commonly used by a person skilled in the art, such as a solution, a gel, a cream, an emulsion, an ointment, a cream, a paste, a cake, a powder, a patch, a spray product and other cosmetically acceptable carriers.

First, fibroblast survival experiment

Test samples:

formulation A

The hydroxypropyl tetrahydropyrane triol compound comprises the following components in percentage by mass:

5.0-10.0% of hydroxypropyl tetrahydropyrane triol, 5-10% of dihydric alcohol, 0.2-0.4% of p-hydroxyacetophenone and 81-88% of deionized water.

Formulation B

5.0-10.0 percent of hydroxypropyl tetrahydropyrane triol, 0.1-0.5 percent of high molecular sodium hyaluronate, 0.5-1.0 percent of low molecular sodium hyaluronate, 0.1-0.5 percent of hydrolyzed sodium hyaluronate, 1.0-5.0 percent of acetyl chitosamine, 0.2-0.4 percent of p-hydroxyacetophenone, 2.6-5 percent of propylene glycol, 0.4-1 percent of hexanediol, 2-4 percent of pentanediol, and the balance of deionized water, wherein the sum of the mass percentages of the components is 100 percent.

Formulation C

5.0-10.0 percent of hydroxypropyl tetrahydropyrane triol, 0.1-0.5 percent of high molecular sodium hyaluronate, 0.5-1.0 percent of low molecular sodium hyaluronate, 0.1-0.5 percent of hydrolyzed sodium hyaluronate, 1.0-5.0 percent of acetyl chitosamine, 0.1-0.5 percent of collagen, 0.5-2.0 percent of hydrolyzed collagen, 0.2-0.4 percent of p-hydroxyacetophenone, 2.6-5 percent of propylene glycol, 0.4-1 percent of hexanediol, 2-4 percent of pentanediol and the balance of deionized water, wherein the sum of the mass percentages of the components is 100 percent.

Conventional culture of fibroblasts:

1. prepared with a density of0.8～1.0×10⁵A cell suspension of/mL, the cell suspension being seeded in a 96-well cell culture plate at 100. mu.L per well at a temperature of 37. + -. 0.5 ℃, a humidity of > 90%, 5% CO₂Culturing at a concentration of 18-24h under the condition.

2. The stock culture in the well plate was discarded, 100. mu.L of 1% strength different test samples, blank control and the hydroxypropyl tetrahydropyran triol complex of A, B and C were added to each well, labeled, and returned to the incubator for 24. + -. 1 hours. The wells without sample were used as blank control and 10% DMSO was used as positive control.

3. The plates were removed and 20. mu.L of MTT solution was added to each well and the incubator was incubated for 3-4 hours. Removing liquid in the pore plate, adding 100 mu L DMSO into each pore, placing in an oscillator, oscillating for 10-15min, and measuring absorbance at 570nm wavelength of a microplate reader.

TABLE 1 fibroblast relative cell Activity test results

4. And (4) analyzing results:

as can be seen from table 1, compared with the blank control group, the hydroxypropyl tetrahydropyrane triol formulations in A, B and C respectively improve the activity of fibroblasts by 5.28%, 8.31% and 9.59%, which indicates that the hydroxypropyl tetrahydropyrane triol formulations in formula a, formula B and formula C can significantly improve the activity of fibroblasts; because the cell activity A is less than B and less than C, the hydroxypropyl tetrahydropyrane triol, or the sodium hyaluronate, the hydrolyzed sodium hyaluronate and the acetyl chitosamine, or the collagen and the hydrolyzed collagen have the effect of improving the cell activity; and the activity of the fibroblast is obviously improved due to the synergistic effect of the components.

Second, experiment for promoting hyaluronic acid synthesis

The test samples were identical to the fibroblast survival experiments.

1. Human primary representative dermal fibroblasts were routinely cultured and the cells were seeded into 6cm dishes.

2. When the cells grow to be more than 70 percent and are converged, different test samples with the concentration of 1 percent are added, the continuous culture is carried out for 3 days, and the medium is changed once.

3. Meanwhile, each sample is respectively provided with a cell-free group control (only adding a sample to be detected), a blank control group (not containing a substance to be detected) and 50 mu M vitamin C as a positive control, and each group adopts the same treatment mode as the cell group.

4. The supernatant was collected, stored at-80 ℃ and assayed for HA content using an ELISA kit.

5. The relative amount of hyaluronic acid in each group was calculated according to the following formula.

Relative amount of HA = (HA content in experimental group-HA content in cell-free group)/HA content in blank control group X100%

TABLE 2 HA relative content

	Control group	Positive control	A	B	C
						Relative amount of HA	100％	111.25％	120.52％*	128.37％*	132.29％**

P value < 0.05, p value < 0.01

6. And (4) analyzing results:

hyaluronic acid is one of the most representative extracellular glycosaminoglycans and plays important roles in water retention, protection, support, signal transmission and the like in extracellular matrix. As can be seen from table 2, formulations A, B and C increased the amount of endogenous hyaluronic acid by 20.52%, 28.37% and 32.29%, respectively, indicating that both formulations A, B and C promoted the expression of hyaluronic acid synthesis; the promoting effect A of the synthesis of the hyaluronic acid is less than B and less than C, particularly, the hydroxypropyl tetrahydropyrane triol, the hyaluronic acid and the hydrolyzed hyaluronic acid are used as polysaccharides, the chitosan is used as a precursor of the hyaluronic acid, the collagen can effectively improve the activity of fibroblasts, and the active substances possibly have the effect of improving the activity of hyaluronic acid synthase, so that the synthesis amount of the hyaluronic acid is increased.

Third, the experiment for promoting the synthesis of I-type collagen

The test samples were identical to the fibroblast survival experiments.

1. Human prototypical dermal fibroblasts were routinely cultured and seeded into 6-well culture plates until the cells grew to > 70% confluence.

2. The serum-free medium was replaced and the culture was continued for 24 hours.

3. Different test samples were added at 1% concentration and incubated for 48 hours.

4. Meanwhile, a cell-free group control (only adding a sample to be detected) and a blank control group (not containing a substance to be detected) are set, 50 mu M vitamin C is used as a positive control, and each group adopts the same treatment mode as the cell group.

5. Collecting cells, carrying out cell disruption, and testing by adopting an artificial procollagen amino-terminal peptide ELISA kit.

6. The relative amount of collagen in each group was calculated according to the following formula.

Relative amount of i-type collagen ═ collagen content in experimental group-collagen content in cell-free group)/collagen content in blank control group × 100%

TABLE 3 relative expression of type I collagen

	Control group	Positive control	A	B	C
						Relative amount of I-collagen	100％	121.25％	152.35％*	155.80％*	163.51％*

P value < 0.05

7. And (4) analyzing results:

the results in table 3 show that formulas A, B and C respectively increase the expression level of type I collagen by 52.35%, 55.80% and 63.51%, indicating that formulas A, B and C both have significant promoting effects on the expression of type I collagen; and the promotion effect of the synthesis of the I-shaped collagen is that A is more than B and less than C, which shows that the promotion effect of the sodium hyaluronate and the hydrolyzed sodium hyaluronate in the key components of the compound on the I-shaped collagen is more obvious after the synergistic effect of the collagen and the hydrolyzed collagen.

Fourth, collagen synthesis promoting experiment

The test samples were identical to the fibroblast survival experiments.

4. Meanwhile, a blank control group (containing no substance to be detected) is set, and each group adopts the same treatment mode as the cell group.

5. Cells were collected, disrupted and tested using human elastin ELISA kit.

6. The relative amount of elastin in each group was calculated according to the following formula.

Collagen content in experimental group/collagen content in blank control group × 100%

TABLE 4 relative expression of elastin

	Control group	Positive control	A	B	C
						Relative amount of elastin	100％	141.52％*	139.83％*	153.79％*	148.50％*

P value < 0.05

7. And (4) analyzing results:

the results in table 4 show that the formula a, the formula B and the formula C respectively increase the expression level of the type I collagen by 39.83%, 53.79% and 48.50%, which indicates that the formula a, the formula B and the formula C all have significant effects on promoting the expression of human elastin.

Fifthly, the formula C is utilized to prepare moisturizing and activating essence D

1. Testing the model: testing volunteers, randomly and blindly testing, wherein 30 20-60-year-old healthy women are marked with 4cm multiplied by 4cm on the curved sides of forearms of left and right hands as test areas, respectively smearing moisturizing and activating essence D and moisturizing essence matrix, and respectively using the moisturizing and activating essence D and the moisturizing essence matrix once a day in the morning and at night, wherein the test period is 28 days, and other skin care products are not used in the period.

2. The formula of the essence liquid is as follows:

moisture-retention essence matrix: water, glycerin, carbomer, pentanediol and triethanolamine

Moisturizing and activating essence D: water, hydroxypropyl tetrahydropyrane triol compound C, glycerin, carbomer, pentanediol and triethanolamine

3. And (3) testing:

and respectively testing the moisture content of the skin by using a skin moisture tester on 0 th day, 3 th day, 7 th day, 14 th day, 21 th day and 28 th day.

4. And (3) testing results:

TABLE 5 relative values of skin moisture content (%)

*p＜0.05

5. And (4) analyzing results:

as can be seen from the above table, compared with the moisturizing essence matrix, the moisturizing and activating essence D has a relatively obvious improvement in skin moisture in 14 days of the fourteenth day, and the relative water content of the skin is increased by about 14% in 28 days of the twenty-eighth day, which indicates that the addition of the hydroxypropyl tetrahydropyrane triol complex C has a significant promotion effect on the moisturizing effect of the essence.

Sixthly, the formula C is utilized to prepare the line carving inverse aged emulsion E

1. Testing the model: randomly and blindly testing, selecting 30 20-60-year-old healthy women, respectively coating the left half face and the right half face with the line carving inverse-age emulsion E and the anti-wrinkle cream matrix, respectively using the line carving inverse-age emulsion E and the anti-wrinkle cream matrix once in the morning and at the evening every day, and testing for 28 days without using other skin care products in the period.

2. The formula of the emulsion comprises:

anti-wrinkle milk matrix: water, glycerin, cyclohexasiloxane, glyceryl stearate, pentanediol

Line carving inverse aged milk E: water, hydroxypropyl tetrahydropyrane triol compound C, glycerin, cyclohexasiloxane, glyceryl stearate, pentanediol

3. And (3) testing:

the skin elasticity tester is used for testing the skin elasticity in 0 th day, 3 th day, 7 th day, 14 th day, 21 th day and 28 th day.

4. And (3) testing results:

TABLE 6 relative values of skin elasticity R2 (%)

*p＜0.05

5. And (4) analyzing results:

as can be seen from the above table, compared with the anti-wrinkle cream matrix, the line-engraved retro-aged cream E has the effect of improving the skin elasticity in 7 days of the seventh day, the skin elasticity is obviously improved in 14 days of the fourteenth day, and the relative value of the skin elasticity is increased by about 12% in 28 days of the twenty-eighth day, which shows that the hydroxypropyl tetrahydropyrane triol compound C is beneficial to obviously improving the skin elasticity by the line-engraved retro-aged cream, so that the anti-wrinkle cream has the anti-aging effects of smoothing fine lines, fading wrinkles and the like.

Hyaluronic acid (glycosaminoglycans and the like), type I collagen and elastin are important constituent structures of human skin extracellular matrix (ECM), and when hyaluronic acid, type I collagen and elastin are lost or expressed in insufficient amounts in the skin, water in the skin is easily lost, the dermis is easily shrunken, the skin elasticity is reduced, fine lines are formed, and wrinkles are generated. According to efficacy tests of the hydroxypropyl tetrahydropyran compound formula A, the formula B and the formula C, the formula A, the formula B and the formula C can promote the expression of hyaluronic acid, type I collagen and elastin, and the three can be helpful for enriching and improving the extracellular matrix ECM of human skin, so that the skin is full and healthy. After the hydroxypropyl tetrahydropyran compound C is added into the essence (D) and the emulsion (E), the test result shows that the hydroxypropyl tetrahydropyran triol compound C can obviously improve the moisture content of the skin and the elasticity of the skin.

The hydroxypropyl tetrahydropyrane triol complex provided by the invention can be directly applied as a skin care product essence, can also be used as an effective component in a cosmetic formula to be compatible with other components, and the other active components such as alpha-arbutin, nicotinamide, ceramide, vitamin C and derivatives thereof, allantoin, glycyrrhizic acid, betaine, small molecule peptides, plant extracts, fuguyin and the like can compensate or enhance the effects of the cosmetic in other aspects by being compounded with the other active components. The cosmetic of the present invention may also use other preservatives in place of or in part of glycols and/or p-hydroxyacetophenone, such as one or more of phenoxyethanol, ethylhexylglycerin, methylparaben, ethylparaben, propylparaben, octanoylketone, octanoylhydroxamic acid, benzyl alcohol, benzoic acid, benzalkonium chloride, imidazolidinyl urea, hydantoin, isothiazolinone, and the like, to construct a preservative system.

The cosmetic containing the hydroxypropyl tetrahydropyran compound provided by the invention has at least one skin care effect of resisting aging, tightening, improving skin elasticity, moisturizing, fading fine lines, repairing, improving skin quality, brightening skin color and the like.

It should be noted that the hydroxypropyl tetrahydropyrane triol composition obtained in the above embodiment and the above formula a, formula B and formula C may be used alone or in combination in cosmetic formulations, including but not limited to facial care, hand care, body care, head care, nail care, mouth care and lip care products.

In conclusion, the product prepared by the formula can be applied to skin care products, and cell experiments prove that the formula can improve the activity of fibroblasts, promote the synthesis of hyaluronic acid in the fibroblasts, improve the expression of type I collagen, up-regulate the expression level of elastin, and has the effects of moisturizing and increasing skin elasticity. The hydroxypropyl tetrahydropyrane triol, hyaluronic acid and/or salt thereof with different molecular weights, hydrolyzed hyaluronic acid and/or salt thereof have a synergistic effect after being compounded, and the addition of the acetyl chitosamine, the collagen and the hydrolyzed collagen further enhances the activity of the synergistic effect, thereby expanding the application of the hydroxypropyl tetrahydropyrane triol in the formula of the skin care product.

When the components of the hydroxypropyl tetrahydropyrane triol compound are prepared according to a proper mass ratio, a better synergistic skin care effect can be shown, for example, according to a formula A, B, C, under the condition that the addition amount of the components in the skin care product is the same, the comprehensive skin care effect of a formula A, B, C is sequentially enhanced. Compared with single components, the active components are compounded according to a proper proportion, and the formula A, B, C can ensure that the cosmetics have comprehensive and positive moisturizing and anti-aging effects.

The advantageous effects of the present invention will now be described in detail with reference to examples.

Example 1

8% of hydroxypropyl tetrahydropyrane triol, 0.4% of high-molecular sodium hyaluronate, 0.9% of low-molecular sodium hyaluronate, 0.4% of hydrolyzed sodium hyaluronate, 4.0% of acetyl chitosamine, 9% of dihydric alcohol, 0.3% of p-hydroxyacetophenone and the balance of deionized water, wherein the sum of the mass percentages of the components is 100%.

Example 2

10% of hydroxypropyl tetrahydropyrane triol, 0.3% of high-molecular sodium hyaluronate, 0.8% of low-molecular hyaluronic acid, 0.1% of hydrolyzed hyaluronic acid, 5% of propylene glycol, 1% of hexanediol, 3% of pentanediol, 0.4% of p-hydroxyacetophenone, 0.5% of collagen, 2.0% of hydrolyzed collagen, 3.0% of acetyl chitosamine and the balance of deionized water, wherein the sum of the mass percentages of the components is 100%.

Example 3

6% of hydroxypropyl tetrahydropyrane triol, 0.4% of high-molecular sodium hyaluronate, 0.6% of low-molecular sodium hyaluronate, 0.2% of hydrolyzed sodium hyaluronate, 2% of acetyl chitosamine, 0.1% of collagen, 0.5% of hydrolyzed collagen, 0.2% of p-hydroxyacetophenone, 2.6% of propylene glycol, 0.4% of hexanediol, 2% of pentanediol and the balance of deionized water, wherein the sum of the mass percentages of the components is 100%.

Example 4

1% of hydroxypropyl tetrahydropyrane triol, 0.8% of high-molecular potassium hyaluronate, 2% of low-molecular potassium hyaluronate, 1.05% of hydrolyzed hyaluronic acid, 1.5% of collagen, 1.0% of hydrolyzed collagen, 5.0% of acetyl chitosamine, 5.0% of dihydric alcohol and the balance of deionized water, wherein the sum of the mass percentages of the components is 100%.

Example 5

40% of hydroxypropyl tetrahydropyrane triol, 0.05% of high-molecular potassium hyaluronate, 0.05% of low-molecular hyaluronic acid, 0.05% of hydrolyzed sodium hyaluronate, 0.05% of collagen, 0.05% of hydrolyzed collagen, 1.0% of acetyl chitosamine, 5.0% of dihydric alcohol and the balance of deionized water, wherein the sum of the mass percentages of the components is 100%.

Example 6

20% of hydroxypropyl tetrahydropyrane triol, 0.1% of high-molecular potassium hyaluronate, 1.9% of low-molecular potassium hyaluronate, 0.5% of hydrolyzed hyaluronic acid, 0.2% of collagen, 1.5% of hydrolyzed collagen, 4.5% of acetyl chitosamine, 9.0% of dihydric alcohol and the balance of deionized water, wherein the sum of the mass percentages of the components is 100%.

Example 7

30% of hydroxypropyl tetrahydropyrane triol, 0.2% of high-molecular sodium hyaluronate, 0.15% of low-molecular potassium hyaluronate, 1% of hydrolyzed sodium hyaluronate, 0.3% of collagen, 0.25% of hydrolyzed collagen, 2.0% of acetyl chitosamine, 6.0% of dihydric alcohol and the balance of purified water, wherein the sum of the mass percentages of the components is 100%.

Example 8

25% of hydroxypropyl tetrahydropyrane triol, 0.7% of high molecular hyaluronic acid, 1.5% of low molecular hyaluronic acid, 2% of hydrolyzed hyaluronic acid, 0.4% of collagen, 1.7% of hydrolyzed collagen, 2.5% of chitosamine, 8% of dihydric alcohol and the balance of purified water, wherein the sum of the mass percentages of the components is 100%.

Example 9

the molecular weight of the high molecular hyaluronic acid and/or the salt thereof is 220 ten thousand Da, the molecular weight of the low molecular hyaluronic acid is 50 ten thousand Da, the molecular weight of the hydrolyzed hyaluronic acid is 1 ten thousand Da, the molecular weight of the collagen is 8 ten thousand Da, and the molecular weight of the hydrolyzed collagen is 5000 Da.

Example 10

the molecular weight of the high molecular weight hyaluronic acid and/or the salt thereof is 70 ten thousand Da, the molecular weight of the low molecular weight hyaluronic acid and/or the salt thereof is 5 ten thousand Da, the molecular weight of the hydrolyzed hyaluronic acid and/or the salt thereof is 5000Da, the molecular weight of the collagen is 2 ten thousand Da, and the molecular weight of the hydrolyzed collagen is 200 Da.

Example 11

A hydroxypropyl tetrahydropyran triol complex, comprising the following components:

the molecular weight of the high molecular weight hyaluronic acid and/or the salt thereof is 120 ten thousand Da, the molecular weight of the low molecular weight hyaluronic acid and/or the salt thereof is 10 ten thousand Da, the molecular weight of the hydrolyzed hyaluronic acid and/or the salt thereof is 400Da, the molecular weight of the collagen is 5 ten thousand Da, and the molecular weight of the hydrolyzed collagen is 1000 Da.

Example 12

the molecular weight of the high molecular weight hyaluronic acid and/or the salt thereof is 150 ten thousand Da, the molecular weight of the low molecular weight hyaluronic acid and/or the salt thereof is 40 ten thousand Da, the molecular weight of the hydrolyzed hyaluronic acid and/or the salt thereof is 2000Da, the molecular weight of the collagen is 3 ten thousand Da, and the molecular weight of the hydrolyzed collagen is 3000 Da.

Example 13

A method of preparing the hydroxypropyl tetrahydropyran triol formulation of example 2 comprising the steps of:

s202: adding propylene glycol, high molecular sodium hyaluronate and low molecular hyaluronic acid into an emulsifying tank, and fully wetting and dispersing;

s204: adding deionized water, heating to 79 ℃, stirring to obtain a transparent uniform solution, and keeping the temperature for 60 minutes for later use;

s206: when the temperature is reduced to 50 ℃, adding the hydroxypropyl tetrahydropyrane triol compound, and fully stirring and dissolving to obtain a uniform solution;

s208: and after the temperature of the uniform solution is reduced to normal temperature, adding hydrolyzed hyaluronic acid, acetyl chitosamine, hexanediol, pentanediol and p-hydroxyacetophenone, and uniformly stirring until the mixture is completely dissolved, thereby obtaining the hydroxypropyl tetrahydropyrane triol compound.

Example 14

A method for preparing a hydroxypropyl tetrahydropyrane triol compound comprises the following components in percentage by mass: 0.8% of high-molecular-weight potassium hyaluronate, 2% of low-molecular-weight potassium hyaluronate, 1.05% of hydrolyzed hyaluronic acid, 1.5% of collagen, 1.0% of hydrolyzed collagen, 1.65% of chitosamine, 5.0% of dihydric alcohol and the balance of purified water, wherein the sum of the mass percentages of the components is 100%, and the method comprises the following steps:

s202: adding propylene glycol, high molecular potassium hyaluronate and low molecular potassium hyaluronate into an emulsifying tank, and fully wetting and dispersing;

s204: adding the rest of deionized water, heating to 69 ℃, stirring to obtain a transparent uniform solution, and keeping the temperature for 10 minutes for later use;

s206: when the temperature is reduced to 30 ℃, adding the hydroxypropyl tetrahydropyrane triol compound, and fully stirring and dissolving to obtain a uniform solution;

Example 15

A method of preparing the hydroxypropyl tetrahydropyran triol formulation of example 3 comprising the steps of:

s202: adding propylene glycol, high molecular sodium hyaluronate and low molecular sodium hyaluronate into an emulsifying tank, and fully wetting and dispersing;

s204: adding the rest of deionized water, heating to 50 ℃, stirring to obtain a transparent uniform solution, and keeping the temperature for 28 minutes for later use;

s206: when the temperature is reduced to 38 ℃, adding the hydroxypropyl tetrahydropyrane triol compound, and fully stirring and dissolving to obtain a uniform solution;

s208: and after the temperature of the uniform solution is reduced to normal temperature, adding hydrolyzed sodium hyaluronate, acetyl chitosamine, hexanediol, pentanediol and p-hydroxyacetophenone, and uniformly stirring until the materials are completely dissolved, thereby obtaining the hydroxypropyl tetrahydropyrane triol compound.

Example 16

A method of preparing the hydroxypropyl tetrahydropyran triol formulation of example 8 comprising the steps of:

s202: adding propylene glycol, high molecular hyaluronic acid and low molecular hyaluronic acid into an emulsifying tank, and fully wetting and dispersing;

s204: adding deionized water, heating to 60 ℃, stirring to obtain a transparent uniform solution, and keeping the temperature for 40 minutes for later use;

s206: when the temperature is reduced to 47 ℃, adding the hydroxypropyl tetrahydropyrane triol compound, and fully stirring and dissolving to obtain a uniform solution;

Example 17

A face cream, wherein the mass content of the hydroxypropyl tetrahydropyrane triol compound in example 4 is 15%.

Example 18

A hand lotion, wherein the mass content of the hydroxypropyl tetrahydropyrane triol compound in example 5 is 0.5%.

Example 19

An emulsion wherein the mass content of the hydroxypropyl tetrahydropyran triol formulation in example 7 is 20%.

Example 20

A lipstick, wherein the mass content of the hydroxypropyl tetrahydropyran triol compound in the example 7 is 10%.

The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and it will be apparent to those skilled in the art that the embodiments of the present invention and features of the embodiments may be combined with each other to obtain a new embodiment without conflict, and various modifications and changes may be made in the present invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims

1. A hydroxypropyl tetrahydropyran triol complex characterized by comprising hydroxypropyl tetrahydropyran triol, hyaluronic acid and/or a salt thereof, hydrolyzed hyaluronic acid and/or a salt thereof, chitosamine (a precursor of hyaluronic acid), deionized water, an ingredient having a preservative effect or a preservative.

2. The hydroxypropyl tetrahydropyran triol formulation according to claim 1, wherein the preservative is selected from the group consisting of glycols and p-hydroxyacetophenone, the preservative is selected from one or more of phenoxyethanol, ethylhexylglycerol, methylparaben, ethylparaben, propylparaben, octanoylketone, octanoylhydroxamic acid, benzyl alcohol, benzoic acid, benzalkonium chloride, imidazolidinyl urea, hydantoin, and isothiazolinone, and the deionized water is purified water; preferably, the dihydric alcohol is any one or more of propylene glycol, pentanediol, hexanediol and butanediol;

preferably, the salt of hyaluronic acid and the salt of hydrolyzed hyaluronic acid are any one or more of sodium salt, potassium salt, zinc salt and calcium salt.

3. The hydroxypropyl tetrahydropyran triol formulation according to claim 1, wherein the hyaluronic acid and/or salt thereof comprises a high molecular weight hyaluronic acid and/or salt thereof, a low molecular weight hyaluronic acid and/or salt thereof.

4. The hydroxypropyl tetrahydropyran triol formulation according to any one of claims 1 to 3 further comprising collagen and hydrolyzed collagen.

5. The hydroxypropyl tetrahydropyran triol formulation according to claim 4, wherein the molecular weight of the high molecular weight hyaluronic acid and/or the salt thereof is 70-220 ten thousand Da, the molecular weight of the low molecular weight hyaluronic acid and/or the salt thereof is 5-50 ten thousand Da, the molecular weight of the hydrolyzed hyaluronic acid and/or the salt thereof is 400-1 ten thousand Da, the molecular weight of the collagen is 2-8 ten thousand Da, and the molecular weight of the hydrolyzed collagen is 200-5000 Da;

preferably, the molecular weight of the high molecular hyaluronic acid and/or the salt thereof is 120-150 ten thousand Da, the molecular weight of the low molecular hyaluronic acid and/or the salt thereof is 10-40 ten thousand Da, the molecular weight of the hydrolyzed hyaluronic acid and/or the salt thereof is 400-1 ten thousand Da, the molecular weight of the collagen is 2-8 ten thousand Da, and the molecular weight of the hydrolyzed collagen is 200-5000 Da.

6. The hydroxypropyl tetrahydropyran triol formulation according to claim 4, characterized in that the components are in mass proportion: 1-50% of hydroxypropyl tetrahydropyrane triol, 0.05-0.8% of high molecular hyaluronic acid and/or salt thereof, 0.05-2% of low molecular hyaluronic acid and/or salt thereof, 0.05-2% of hydrolyzed hyaluronic acid and/or salt thereof, 0.05-0.5% of collagen, 0.05-2.0% of hydrolyzed collagen, 1.0-5.0% of chitosan, 5.0-10.0% of dihydric alcohol, 0-0.5% of p-hydroxyacetophenone and the balance of deionized water, wherein the sum of the mass percentages of the components is 100%;

preferably, the components are as follows according to mass ratio: 5-20% of hydroxypropyl tetrahydropyrane triol, 0.1-0.5% of high molecular hyaluronic acid and/or salt thereof, 0.5-1.5% of low molecular hyaluronic acid and/or salt thereof, 0.1-0.5% of hydrolyzed hyaluronic acid and/or salt thereof, 0.05-0.5% of collagen, 0.05-2.0% of hydrolyzed collagen, 1.0-5.0% of chitosan, 5.0-10.0% of dihydric alcohol, 0-0.5% of p-hydroxyacetophenone and the balance of deionized water, wherein the sum of the mass percentages of the components is 100%.

7. A process for the preparation of a hydroxypropyl tetrahydropyran triol formulation according to any one of claims 1 to 3 comprising the steps of:

8. A process for the preparation of a hydroxypropyl tetrahydropyran triol formulation according to any one of claims 4 to 6 comprising the steps of:

9. A cosmetic comprising a hydroxypropyl tetrahydropyran triol formulation according to any one of claims 1 to 8;

preferably, the mass content of the hydroxypropyl tetrahydropyrane triol compound is 0.1-20%;

preferably, the cosmetic also comprises one or more of alpha-arbutin, nicotinamide, ceramide, vitamin C and its derivatives, allantoin, glycyrrhizic acid, betaine, small molecule peptides, plant extract, and fubotine.

10. Use of a hydroxypropyl tetrahydropyran triol formulation according to any one of claims 1 to 8 in the preparation of a facial care, hand care, body care, head care, nail care, mouth care and lip care product.