CN111568798A - Skin care material and preparation method thereof - Google Patents

Skin care material and preparation method thereof Download PDF

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Publication number
CN111568798A
CN111568798A CN202010486281.1A CN202010486281A CN111568798A CN 111568798 A CN111568798 A CN 111568798A CN 202010486281 A CN202010486281 A CN 202010486281A CN 111568798 A CN111568798 A CN 111568798A
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skin care
care material
nicotinamide
methyl
thiosemicarbazide
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王美香
刘海霞
张秀燕
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/673—Vitamin B group
    • A61K8/675—Vitamin B3 or vitamin B3 active, e.g. nicotinamide, nicotinic acid, nicotinyl aldehyde
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/87—Polyurethanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/02—Local antiseptics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/592—Mixtures of compounds complementing their respective functions

Abstract

The invention discloses a skin care material which is characterized by being prepared from the following raw materials in parts by weight: 0.1-0.2 part of methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium, 20-30 parts of beta-nicotinamide adenine dinucleotide modified epoxy-terminated hyperbranched poly (amine-ester) and 10-15 parts of cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer. The invention also provides a preparation method of the skin care material. The skin care material disclosed by the invention has better biocompatibility and better skin care effect, can promote the wound to heal quickly, and has the effects of beautifying, moisturizing, removing freckles and resisting aging.

Description

Skin care material and preparation method thereof
Technical Field
The invention relates to the technical field of nursing materials, in particular to a skin nursing material and a preparation method thereof.
Background
Nowadays, social substance life is more and more abundant, people also focus on the appearance problem of the people more and more, skin care materials become most people, especially the most popular choice of contemporary women, and good skin care products can play the effects of promoting skin blood circulation, repairing skin injury, removing wrinkles, increasing skin elasticity and luster, caring sensitive skin and the like.
Skin care materials on the market, while improving the appearance of healthy skin, do not provide significant care for the affected skin. In addition to the problems of single function, poor biocompatibility and antibacterial and anti-infection performance, the nursing effect needs to be further improved, the effect of preventing bacterial infection cannot be well achieved, wound inflammation and suppuration are easily caused, the wound recovery condition is inconvenient to observe, and the defects of no convenience for timely treatment are overcome.
The Chinese invention patent with the application number of 201810706541.4 discloses an application of a skin care composition in diabetic foot care or suture wound care, wherein the skin care composition comprises the following components in percentage by weight: 1 to 20 percent of film-forming agent, 0.5 to 10 percent of thickening agent, 0.5 to 10 percent of plasticizer, 0.01 to 2 percent of bacteriostatic agent, 0.01 to 2 percent of skin conditioning agent and the balance of solvent. The skin care composition forms a transparent film with suitable toughness and strength after being coated on skin, and the transparent film also has good moisture resistance, rubbing resistance, water resistance and antibacterial activity. However, the composition contains a solvent component, and is irritating to the skin, so that the care effect is to be further improved.
Therefore, the development of the skin care material which has better biocompatibility and skin care effect, can promote the wound to heal quickly, has the effects of beautifying, moisturizing, removing freckles and resisting aging meets the market demand, has wide market value and application prospect, and plays a vital role in promoting the development of the field of skin care.
Disclosure of Invention
In view of the above, the invention aims to provide a skin care material and a preparation method thereof, wherein the preparation method has the advantages of simple process, convenient operation, wide sources of preparation raw materials, low preparation cost, high preparation efficiency and high yield, and is suitable for continuous large-scale production; the skin care material prepared by the preparation method has better biocompatibility and skin care effect, can promote the wound to heal quickly, and has the effects of beautifying, moisturizing, removing freckles and resisting aging.
In order to achieve the purpose, the invention adopts the technical scheme that:
the skin care material is characterized by being prepared from the following raw materials in parts by weight: 0.1-0.2 part of methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium, 20-30 parts of beta-nicotinamide adenine dinucleotide modified epoxy-terminated hyperbranched poly (amine-ester) and 10-15 parts of cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer.
Preferably, the preparation method of the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetrakis (dimethylamino) germanium comprises the following steps: adding methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside and tetra (dimethylamino) germanium into an organic solvent, stirring and reacting for 6-8 hours at 40-60 ℃, then performing rotary evaporation to remove the solvent, washing the product for 3-7 times by using diethyl ether, and then performing rotary evaporation to remove the diethyl ether to obtain the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium.
Preferably, the molar ratio of the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside to the tetra (dimethylamino) germanium to the organic solvent is 4:1 (18-28).
Preferably, the organic solvent is any one of tetrahydrofuran, N-dimethylformamide, N-dimethylacetamide and N-methylpyrrolidone.
Preferably, the preparation method of the beta-nicotinamide adenine dinucleotide modified epoxy-terminated hyperbranched poly (amine-ester) comprises the following steps: adding beta-nicotinamide adenine dinucleotide, epoxy terminal hyperbranched poly (amine-ester) and an alkaline catalyst into a high boiling point solvent, stirring and reacting for 4-7 hours at 70-80 ℃, then precipitating in water, filtering to obtain a precipitated polymer, and drying to constant weight in a vacuum drying oven at 90-100 ℃ to obtain the beta-nicotinamide adenine dinucleotide modified epoxy terminal hyperbranched poly (amine-ester).
Preferably, the mass ratio of the beta-nicotinamide adenine dinucleotide, the epoxy-terminated hyperbranched poly (amine-ester), the alkaline catalyst and the high-boiling-point solvent is 0.3 (3-5): (0.3-0.6): 20-30.
Preferably, the alkaline catalyst is at least one of sodium hydroxide, sodium carbonate, potassium hydroxide and potassium carbonate; the high boiling point solvent is at least one of dimethyl sulfoxide, N-dimethylformamide, N-dimethylacetamide and N-methylpyrrolidone.
Preferably, the preparation method of the epoxy terminal hyperbranched poly (trimethylene-co-trimethylene ester) is described in Chinese patent application No. 200910067539.8, example 6.
Preferably, the preparation method of the cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer comprises the following steps: adding cinnamic acid, N-allyl nicotinamide, macelignan, 4-propenyl thiosemicarbazide and an initiator into N-methyl pyrrolidone, stirring and reacting for 3-5 hours at 65-75 ℃ in the atmosphere of nitrogen or inert gas, and then removing the solvent by rotary evaporation to obtain the cinnamic acid/N-allyl nicotinamide/macelignan/4-propenyl thiosemicarbazide copolymer.
Preferably, the mass ratio of the cinnamic acid, the N-allyl nicotinamide, the myristyl lignanoid, the 4-propenyl thiosemicarbazide, the initiator and the N-methylpyrrolidone is 1:1:0.7:0.2 (0.02-0.04) to (10-18).
Preferably, the initiator is at least one of azobisisobutyronitrile and azobisisoheptonitrile; the inert gas is any one of helium, neon and argon.
Another object of the present invention is to provide a method for preparing the skin care material, which comprises the following steps: the skin care material is prepared by uniformly mixing the raw materials in parts by weight to obtain a mixed material, adding the mixed material into a double-screw extruder for extrusion molding, and cooling to room temperature after molding.
Adopt the produced beneficial effect of above-mentioned technical scheme to lie in:
(1) the preparation method of the skin care material provided by the invention is simple in process, convenient to operate, wide in source of preparation raw materials, low in preparation cost, high in preparation efficiency and yield and suitable for continuous large-scale production.
(2) The skin care material provided by the invention overcomes the defects that the traditional skin care material has an unobvious care effect on the wounded skin, the skin care materials are often torn in the using process, or have poor adhesion and poor strength, or have strong antigenicity and strong irritation, or have poor permeability, are susceptible to infection, or hinder the growth of autogenous skin and cause scar accumulation, or have low raw material source, high cost, or have complex process, difficult manufacture and difficult storage, besides, the existing skin care material has more or less defects of single function, poor biocompatibility and antibacterial anti-infection performance, the care effect needs to be further improved, the function of preventing bacterial infection cannot be well achieved, the inflammation and suppuration of wounds are easily caused, the wound recovery condition is inconvenient to observe, and the timely treatment is not facilitated, the skin care cream has the advantages of better biocompatibility, better skin care effect, capability of promoting the wound to heal quickly, and effects of beautifying, moisturizing, removing freckles and resisting aging.
(3) The skin care material provided by the invention is prepared by blending methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium, beta-nicotinamide adenine dinucleotide modified epoxy terminal hyperbranched poly (amine-ester) and cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer, wherein the cationic group of the quaternary ammonium salt of the 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium is connected with the carboxyl group on the cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer through ion exchange in an ionic bond, the beta-nicotinamide adenine dinucleotide modified epoxy-terminated hyperbranched poly (amine-ester) enables the molecular chain of the obtained product to contain residual epoxy groups by controlling the amount of raw materials in the modification process, the residual epoxy groups are easy to generate a ring-opening reaction on the amino group on the cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer, and all the components are connected together in a chemical bond form to form a three-dimensional network structure, so that the comprehensive performance of the material is effectively improved, and the material has a higher improvement effect on the mechanical property.
(4) According to the skin care material provided by the invention, the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium is added, under the introduction of glycoside groups, the moisture retention performance of the material is effectively improved, and the skin moistening effect is achieved.
(5) According to the skin care material provided by the invention, under the action of the beta-nicotinamide adenine dinucleotide structure on the beta-nicotinamide adenine dinucleotide modified epoxy terminal hyperbranched poly (amine-ester), the material has the effects of beautifying, moisturizing and removing freckles, and the hyperbranched structure is adopted, so that the biocompatibility of the material is effectively improved, the touch feeling of the material when the material is in contact with the skin is improved, and the anaphylactic reaction is reduced. Due to the addition of the cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer and the synergistic effect of all structural units, the skin care effect of the material is remarkable, and the effects of resisting aging, removing freckles, whitening and moisturizing are obvious.
Detailed Description
In order to make the technical solutions of the present invention better understood and make the above features, objects, and advantages of the present invention more comprehensible, the present invention is further described with reference to the following examples. The examples are intended to illustrate the invention only and are not intended to limit the scope of the invention.
In the embodiment of the invention, the raw materials are all purchased commercially; the preparation method of the epoxy terminal hyperbranched poly (trimethylene-co-trimethylene) is shown in the Chinese patent application No. 200910067539.8, namely the example 6.
Example 1
The skin care material is characterized by being prepared from the following raw materials in parts by weight: 0.1 part of methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium, 20 parts of beta-nicotinamide adenine dinucleotide modified epoxy-terminated hyperbranched poly (amine-ester) and 10 parts of cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer.
The preparation method of the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium comprises the following steps: adding methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside and tetra (dimethylamino) germanium into tetrahydrofuran, stirring and reacting for 6 hours at 40 ℃, then performing rotary evaporation to remove the solvent, washing the product with diethyl ether for 3 times, and performing rotary evaporation to remove the diethyl ether to obtain methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium; the molar ratio of the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside to the tetra (dimethylamino) germanium to the tetrahydrofuran is 4:1: 18.
The preparation method of the beta-nicotinamide adenine dinucleotide modified epoxy terminal hyperbranched poly (amine-ester) comprises the following steps: adding beta-nicotinamide adenine dinucleotide, epoxy terminal hyperbranched poly (amine-ester) and sodium hydroxide into dimethyl sulfoxide, stirring and reacting for 4 hours at 70 ℃, then precipitating in water, filtering to obtain a precipitated polymer, and drying in a vacuum drying oven at 90 ℃ to constant weight to obtain beta-nicotinamide adenine dinucleotide modified epoxy terminal hyperbranched poly (amine-ester); the mass ratio of the beta-nicotinamide adenine dinucleotide, the epoxy terminal hyperbranched poly (amine-ester), the sodium hydroxide and the dimethyl sulfoxide is 0.3:3:0.3: 20.
The preparation method of the cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer comprises the following steps: adding cinnamic acid, N-allyl nicotinamide, macelignan, 4-propenyl thiosemicarbazide and azodiisobutyronitrile into N-methylpyrrolidone, stirring and reacting for 3 hours at 65 ℃ in a nitrogen atmosphere, and then removing the solvent by rotary evaporation to obtain a cinnamic acid/N-allyl nicotinamide/macelignan/4-propenyl thiosemicarbazide copolymer; the mass ratio of the cinnamic acid to the N-allyl nicotinamide to the myristol to the 4-propenyl thiosemicarbazide to the azodiisobutyronitrile to the N-methylpyrrolidone is 1:1:0.7:0.2:0.02: 10.
A preparation method of the skin care material is characterized by comprising the following steps: the skin care material is prepared by uniformly mixing the raw materials in parts by weight to obtain a mixed material, adding the mixed material into a double-screw extruder for extrusion molding, and cooling to room temperature after molding.
Example 2
The skin care material is characterized by being prepared from the following raw materials in parts by weight: 0.12 part of methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium, 22 parts of beta-nicotinamide adenine dinucleotide modified epoxy-terminated hyperbranched poly (amine-ester) and 11 parts of cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer.
The preparation method of the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium comprises the following steps: adding methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside and tetra (dimethylamino) germanium into N, N-dimethylformamide, stirring and reacting for 6.5 hours at 45 ℃, then performing rotary evaporation to remove the solvent, washing the product for 4 times by using diethyl ether, and then performing rotary evaporation to remove the diethyl ether to obtain methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium; the molar ratio of the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside to the tetra (dimethylamino) germanium to the N, N-dimethylformamide is 4:1: 20.
The preparation method of the beta-nicotinamide adenine dinucleotide modified epoxy terminal hyperbranched poly (amine-ester) comprises the following steps: adding beta-nicotinamide adenine dinucleotide, epoxy terminal hyperbranched poly (amine-ester) and sodium carbonate into N, N-dimethylformamide, stirring and reacting for 5 hours at 73 ℃, then precipitating in water, filtering to obtain a precipitated polymer, and drying in a vacuum drying oven at 93 ℃ to constant weight to obtain beta-nicotinamide adenine dinucleotide modified epoxy terminal hyperbranched poly (amine-ester); the mass ratio of the beta-nicotinamide adenine dinucleotide, the epoxy terminal hyperbranched poly (amine-ester), the sodium carbonate and the N, N-dimethylformamide is 0.3:3.5:0.4: 23.
The preparation method of the cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer comprises the following steps: adding cinnamic acid, N-allyl nicotinamide, macelignan, 4-propenyl thiosemicarbazide and azodiisoheptanonitrile into N-methylpyrrolidone, stirring and reacting for 3.5 hours at 68 ℃ in a helium atmosphere, and then removing the solvent by rotary evaporation to obtain a cinnamic acid/N-allyl nicotinamide/macelignan/4-propenyl thiosemicarbazide copolymer; the mass ratio of the cinnamic acid, the N-allyl nicotinamide, the myristyl lignan, the 4-propenyl thiosemicarbazide, the azodiisoheptanonitrile and the N-methylpyrrolidone is 1:1:0.7:0.2:0.025: 13.
A preparation method of the skin care material is characterized by comprising the following steps: the skin care material is prepared by uniformly mixing the raw materials in parts by weight to obtain a mixed material, adding the mixed material into a double-screw extruder for extrusion molding, and cooling to room temperature after molding.
Example 3
The skin care material is characterized by being prepared from the following raw materials in parts by weight: 0.15 part of methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium, 25 parts of beta-nicotinamide adenine dinucleotide modified epoxy-terminated hyperbranched poly (amine-ester) and 13 parts of cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer.
The preparation method of the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium comprises the following steps: adding methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside and tetra (dimethylamino) germanium into N, N-dimethylacetamide, stirring and reacting for 7 hours at 50 ℃, then performing rotary evaporation to remove the solvent, washing the product for 5 times with diethyl ether, and performing rotary evaporation to remove the diethyl ether to obtain methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium; the molar ratio of the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside to the tetra (dimethylamino) germanium to the N, N-dimethylacetamide is 4:1: 20.
The preparation method of the beta-nicotinamide adenine dinucleotide modified epoxy terminal hyperbranched poly (amine-ester) comprises the following steps: adding beta-nicotinamide adenine dinucleotide, epoxy terminal hyperbranched poly (amine-ester) and potassium hydroxide into N, N-dimethylacetamide, stirring at 75 ℃ for reaction for 6 hours, then precipitating in water, filtering to obtain a precipitated polymer, and drying in a vacuum drying oven at 95 ℃ to constant weight to obtain beta-nicotinamide adenine dinucleotide modified epoxy terminal hyperbranched poly (amine-ester); the mass ratio of the beta-nicotinamide adenine dinucleotide, the epoxy terminal hyperbranched poly (amine-ester), the potassium hydroxide and the N, N-dimethylacetamide is 0.3:4:0.45: 25.
The preparation method of the cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer comprises the following steps: adding cinnamic acid, N-allyl nicotinamide, macelignan, 4-propenyl thiosemicarbazide and azodiisobutyronitrile into N-methylpyrrolidone, stirring and reacting for 4 hours at 70 ℃ in a neon atmosphere, and then removing the solvent by rotary evaporation to obtain a cinnamic acid/N-allyl nicotinamide/macelignan/4-propenyl thiosemicarbazide copolymer; the mass ratio of the cinnamic acid to the N-allyl nicotinamide to the myristol to the 4-propenyl thiosemicarbazide to the azodiisobutyronitrile to the N-methylpyrrolidone is 1:1:0.7:0.2:0.03: 15.
A preparation method of the skin care material is characterized by comprising the following steps: the skin care material is prepared by uniformly mixing the raw materials in parts by weight to obtain a mixed material, adding the mixed material into a double-screw extruder for extrusion molding, and cooling to room temperature after molding.
Example 4
The skin care material is characterized by being prepared from the following raw materials in parts by weight: 0.18 part of methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium, 28 parts of beta-nicotinamide adenine dinucleotide modified epoxy-terminated hyperbranched poly (amine-ester) and 14 parts of cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer.
The preparation method of the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium comprises the following steps: adding methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside and tetra (dimethylamino) germanium into N-methylpyrrolidone, stirring and reacting for 7.5 hours at 55 ℃, then performing rotary evaporation to remove the solvent, washing the product for 6 times by using diethyl ether, and then performing rotary evaporation to remove the diethyl ether to obtain methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium; the molar ratio of the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside to the tetra (dimethylamino) germanium to the N-methylpyrrolidone is 4:1: 27.
The preparation method of the beta-nicotinamide adenine dinucleotide modified epoxy terminal hyperbranched poly (amine-ester) comprises the following steps: adding beta-nicotinamide adenine dinucleotide, epoxy terminal hyperbranched poly (amine-ester) and an alkaline catalyst into a high-boiling-point solvent, stirring and reacting for 6.5 hours at 78 ℃, then precipitating in water, filtering to obtain a precipitated polymer, and drying in a vacuum drying oven at 98 ℃ to constant weight to obtain beta-nicotinamide adenine dinucleotide modified epoxy terminal hyperbranched poly (amine-ester); the mass ratio of the beta-nicotinamide adenine dinucleotide, the epoxy terminal hyperbranched poly (amine-ester), the alkaline catalyst and the high-boiling point solvent is 0.3:4.5:0.55: 28; the alkaline catalyst is prepared by mixing sodium hydroxide, sodium carbonate, potassium hydroxide and potassium carbonate according to the mass ratio of 1:2:3: 2; the high boiling point solvent is formed by mixing dimethyl sulfoxide, N-dimethylformamide, N-dimethylacetamide and N-methylpyrrolidone according to a mass ratio of 1:3:2: 5.
The preparation method of the cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer comprises the following steps: adding cinnamic acid, N-allyl nicotinamide, myristyl lignanoid, 4-propenyl thiosemicarbazide and an initiator into N-methyl pyrrolidone, stirring and reacting for 4.5 hours at 73 ℃ in an argon atmosphere, and then removing the solvent by rotary evaporation to obtain a cinnamic acid/N-allyl nicotinamide/myristyl lignanoid/4-propenyl thiosemicarbazide copolymer; the mass ratio of the cinnamic acid to the N-allylnicotinamide to the myristolignan to the 4-propenyl thiosemicarbazide to the initiator to the N-methylpyrrolidone is 1:1:0.7:0.2:0.035: 17; the initiator is formed by mixing azodiisobutyronitrile and azodiisoheptonitrile according to the mass ratio of 3: 5.
A preparation method of the skin care material is characterized by comprising the following steps: the skin care material is prepared by uniformly mixing the raw materials in parts by weight to obtain a mixed material, adding the mixed material into a double-screw extruder for extrusion molding, and cooling to room temperature after molding.
Example 5
The skin care material is characterized by being prepared from the following raw materials in parts by weight: 0.2 part of methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium, 30 parts of beta-nicotinamide adenine dinucleotide modified epoxy-terminated hyperbranched poly (amine-ester) and 15 parts of cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer.
The preparation method of the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium comprises the following steps: adding methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside and tetra (dimethylamino) germanium into tetrahydrofuran, stirring and reacting for 8 hours at 60 ℃, then performing rotary evaporation to remove the solvent, washing the product with diethyl ether for 7 times, and performing rotary evaporation to remove the diethyl ether to obtain methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium; the molar ratio of the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside to the tetra (dimethylamino) germanium to the tetrahydrofuran is 4:1: 28.
The preparation method of the beta-nicotinamide adenine dinucleotide modified epoxy terminal hyperbranched poly (amine-ester) comprises the following steps: adding beta-nicotinamide adenine dinucleotide, epoxy terminal hyperbranched poly (amine-ester) and potassium carbonate into N-methylpyrrolidone, stirring and reacting for 7 hours at 80 ℃, then precipitating in water, filtering to obtain a precipitated polymer, and drying in a vacuum drying oven at 100 ℃ to constant weight to obtain beta-nicotinamide adenine dinucleotide modified epoxy terminal hyperbranched poly (amine-ester); the mass ratio of the beta-nicotinamide adenine dinucleotide, the epoxy terminal hyperbranched poly (amine-ester), the potassium carbonate and the N-methylpyrrolidone is 0.3:5:0.6: 30.
The preparation method of the cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer comprises the following steps: adding cinnamic acid, N-allyl nicotinamide, macelignan, 4-propenyl thiosemicarbazide and azodiisoheptanonitrile into N-methylpyrrolidone, stirring and reacting for 5 hours at 75 ℃ in a nitrogen atmosphere, and then removing the solvent by rotary evaporation to obtain a cinnamic acid/N-allyl nicotinamide/macelignan/4-propenyl thiosemicarbazide copolymer; the mass ratio of the cinnamic acid to the N-allyl nicotinamide to the myristyl lignan to the 4-propenyl thiosemicarbazide to the azodiisoheptanonitrile to the N-methylpyrrolidone is 1:1:0.7:0.2:0.04: 18.
A preparation method of the skin care material is characterized by comprising the following steps: the skin care material is prepared by uniformly mixing the raw materials in parts by weight to obtain a mixed material, adding the mixed material into a double-screw extruder for extrusion molding, and cooling to room temperature after molding.
Comparative example 1
This example provides a skin care material having the same formulation and preparation as example 1, except that no methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetrakis (dimethylamino) germanium is added.
Comparative example 2
This example provides a skin care material having the same formulation and preparation method as example 1, except that no β -nicotinamide adenine dinucleotide-modified epoxy-terminated hyperbranched poly (amine-ester) is added.
Comparative example 3
This example provides a skin care material having the same formulation and preparation method as example 1, except that no cinnamic acid/N-allylnicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer was added.
The skin care materials described in examples 1-5 and comparative examples 1-3 above were subjected to performance testing.
Wherein, the test of water loss on the surface of the material is carried out as follows: cutting the sample material into 5cm diameter circles, soaking in 10% glycerol aqueous solution, removing, applying on human skin for 30 min, taking off the sample material, and measuring water loss on skin surface with CK Electronic multifunctional skin detector, MPA580 model after 15 min. And the antibacterial property, the mechanical property and the biocompatibility of the material are respectively tested according to related national standards, and the test standards and the test results are shown in table 1.
As can be seen from table 1, the skin care material disclosed in the embodiment of the present invention has better antibacterial property and biocompatibility, better mechanical property, and better moisture retention property compared to the comparative example, which is the result of the synergistic effect of the raw materials such as methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetrakis (dimethylamino) germanium, β -nicotinamide adenine dinucleotide modified epoxy-terminated hyperbranched poly (amine-ester), cinnamic acid/N-allylnicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer, and the like.
TABLE 1
Figure BDA0002519349260000101
The foregoing shows and describes the general principles and broad features of the present invention and advantages thereof. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.

Claims (10)

1. The skin care material is characterized by being prepared from the following raw materials in parts by weight: 0.1-0.2 part of methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium, 20-30 parts of beta-nicotinamide adenine dinucleotide modified epoxy-terminated hyperbranched poly (amine-ester) and 10-15 parts of cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer.
2. The skin care material as claimed in claim 1, wherein the preparation method of the ionized tetrakis (dimethylamino) germanium of methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside comprises the following steps: adding methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside and tetra (dimethylamino) germanium into an organic solvent, stirring and reacting for 6-8 hours at 40-60 ℃, then performing rotary evaporation to remove the solvent, washing the product for 3-7 times by using diethyl ether, and then performing rotary evaporation to remove the diethyl ether to obtain the methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside ionized tetra (dimethylamino) germanium.
3. The skin care material as claimed in claim 2, wherein the molar ratio of methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside, germanium tetrakis (dimethylamino) and organic solvent is 4:1 (18-28).
4. The skin care material according to claim 2, wherein the organic solvent is any one of tetrahydrofuran, N-dimethylformamide, N-dimethylacetamide and N-methylpyrrolidone.
5. The skin care material of claim 1, wherein the preparation method of the beta-nicotinamide adenine dinucleotide modified epoxy-terminated hyperbranched poly (amine-ester) comprises the following steps: adding beta-nicotinamide adenine dinucleotide, epoxy terminal hyperbranched poly (amine-ester) and an alkaline catalyst into a high boiling point solvent, stirring and reacting for 4-7 hours at 70-80 ℃, then precipitating in water, filtering to obtain a precipitated polymer, and drying to constant weight in a vacuum drying oven at 90-100 ℃ to obtain the beta-nicotinamide adenine dinucleotide modified epoxy terminal hyperbranched poly (amine-ester).
6. The skin care material of claim 5, wherein the mass ratio of the beta-nicotinamide adenine dinucleotide, the epoxy-terminated hyperbranched poly (amine-ester), the basic catalyst and the high-boiling-point solvent is 0.3 (3-5): (0.3-0.6): 20-30.
7. The skin care material according to claim 5, wherein the basic catalyst is at least one of sodium hydroxide, sodium carbonate, potassium hydroxide and potassium carbonate; the high boiling point solvent is at least one of dimethyl sulfoxide, N-dimethylformamide, N-dimethylacetamide and N-methylpyrrolidone.
8. The skin care material as claimed in claim 1, wherein the preparation method of the cinnamic acid/N-allyl nicotinamide/myristyl lignan/4-propenyl thiosemicarbazide copolymer comprises the following steps: adding cinnamic acid, N-allyl nicotinamide, macelignan, 4-propenyl thiosemicarbazide and an initiator into N-methyl pyrrolidone, stirring and reacting for 3-5 hours at 65-75 ℃ in the atmosphere of nitrogen or inert gas, and then removing the solvent by rotary evaporation to obtain the cinnamic acid/N-allyl nicotinamide/macelignan/4-propenyl thiosemicarbazide copolymer.
9. The skin care material of claim 8, wherein the mass ratio of the cinnamic acid, the N-allylnicotinamide, the myristyl lignan, the 4-propenyl thiosemicarbazide, the initiator and the N-methylpyrrolidone is 1:1:0.7:0.2 (0.02-0.04) to (10-18); the initiator is at least one of azobisisobutyronitrile and azobisisoheptonitrile; the inert gas is any one of helium, neon and argon.
10. A skin treatment material according to any one of claims 1 to 9, wherein the skin treatment material is prepared by a process comprising the steps of: the skin care material is prepared by uniformly mixing the raw materials in parts by weight to obtain a mixed material, adding the mixed material into a double-screw extruder for extrusion molding, and cooling to room temperature after molding.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112535721A (en) * 2020-11-26 2021-03-23 无锡嬿侣生物科技有限公司 Cold compress patch and preparation method thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112535721A (en) * 2020-11-26 2021-03-23 无锡嬿侣生物科技有限公司 Cold compress patch and preparation method thereof

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