Separation and purification method of synthesized 3-hydroxybutyrate oligomers or oligomers and its application in antibacterial and antiviral products

Abstract

The present invention discloses a method for the separation and purification of synthetic 3-hydroxybutyrate oligomers or oligomers and their application in antibacterial and antiviral products. The present invention uses an organometallic complex to catalyze the ring-opening polymerization of lactones to artificially synthesize 3-hydroxybutyrate oligomers or oligomers, uses citric acid to precipitate the organometallic complex catalyst from the reaction mixture, and then uses filtration to remove the precipitate to separate the organometallic complex catalyst from the reaction mixture. Then, by vacuum distillation, low-boiling organic components are removed from the filtrate, and then the distillation temperature is raised to collect the 3-hydroxybutyrate oligomer or oligomer fraction distilled out within a specific temperature range, thereby obtaining purified 3-hydroxybutyrate oligomers or oligomers, which are used as antibacterial and antiviral active components in medical and health and cleaning products.

Description

Technical Field

[0001] The present invention relates to a method for separating and purifying synthetic polymer products, and also relates to using the separated and purified 3-hydroxybutyrate oligomers or oligomers as antibacterial and antiviral active materials to endow related products with antimicrobial properties. More specifically, the synthetic 3-hydroxybutyrate oligomers or oligomers are separated and purified from the mixed crude product in the latter stage of synthesis and used as antibacterial and antiviral biomedical materials. Background Art

[0002] Preventing the spread and infection of pathogenic microorganisms has always been a major public health and safety issue of global concern. Microbial infections not only cause personal infections and diseases, but may even lead to serious global social crises and population decline. In addition, pathogenic microorganisms such as viruses and bacteria are constantly mutating and evolving, and their tolerance to traditional fungicides is increasing. Therefore, there is an urgent need for humans to develop various new types of fungicides that can be widely used in the personal protection of industries such as agriculture, environment, medicine, textile and clothing, food packaging, and medical and health fields to cope with the difficulties and challenges caused by the rapid spread of various types of pathogenic microorganisms and the increasing drug resistance.

[0003] Poly 3-hydroxybutyrate (PHB) is a type of naturally degradable bio-polyester-based polymer material. It is non-toxic and pollution-free. It can be widely used in textiles, food packaging, surgical sutures, and tissue engineering scaffolds. It has good cell compatibility and is not prone to inflammation. At present, there are two main sources of poly 3-hydroxybutyrate. One is synthesized by microbial fermentation, which is extracted, separated, and purified from nutrients and energy storage substances synthesized in microorganisms. This source has a long production cycle and the reaction process is difficult to control. Most of them are used to prepare high-molecular-weight poly 3-hydroxybutyrate products with low requirements for purity. The other method is artificial ring-opening polymerization, which uses β-butyrolactone as a monomer and an organic metal complex as a catalyst. It is synthesized by ring-opening polymerization. The performance parameters of the synthesized poly 3-hydroxybutyrate, including reaction rate, conversion rate, molecular weight and its distribution, can be artificially and reasonably adjusted by controlling the catalyst and reaction physical and chemical conditions. Chinese patent CN110452121A discloses a poly 3-hydroxybutyrate and a mixture of poly 3-hydroxybutyrate and polyethylene glycol having antibacterial activity and used as antibacterial bio-based products and materials. In recent years, the methods for producing and preparing PHB have mostly focused on microbial fermentation or ring-opening polymerization methods. Chinese patent CN101297030A discloses a method for extracting and separating PHB with medium degree of polymerization or high molecular weight from polyhydroxyalkanoates (including PHB) produced by genetically engineered microorganisms and from microbial culture media. Chinese patent CN100448911C discloses a method for extracting polyhydroxyalkanoates (including PHB) in microbial cells. Foreign literature reports a method for synthesizing PHB by ring-opening polymerization using β-butyrolactone as a monomer of PHB in the presence of organic metal catalysts such as tin and rubidium. Chinese patent CN110452115A discloses a method for synthesizing PHB by ring-opening polymerization using aluminum isopropoxide as a catalyst and β-butyrolactone as a monomer.

[0004] Whether it is microbial fermentation or artificial synthesis, the existing known methods for producing PHB inevitably use a large amount of toxic and harmful organic reagents (such as acetone, chloroform or dichloromethane, etc.), which undoubtedly greatly increases the production cost and the difficulty of separation and recovery. In addition, the purity is low and contains more organic impurities, which limits the application of such materials in the fields of biomedicine and tissue engineering. Therefore, an innovative and green method for separating and purifying PHB is needed. Summary of the invention

[0005] An object of the present invention is to provide a method for separating and purifying synthetic 3-hydroxybutyrate oligomers or oligomers which is safe, non-toxic, cost-controlled and has a simple process.

[0006] An object of the present invention is to provide a purified 3-hydroxybutyrate oligomer or oligomer.

[0007] An object of the present invention is to provide the use of a purified 3-hydroxybutyrate oligomer or oligomer in the preparation of antibacterial and / or antiviral products. The 3-hydroxybutyrate oligomer or oligomer can be used as a separate antibacterial and / or antiviral active component, or in combination with other antibacterial or antiviral active components, or can be compounded or copolymerized with other polymer materials, while maintaining good cell compatibility and biodegradability.

[0008] An object of the present invention is to provide an antibacterial product comprising a purified 3-hydroxybutyrate oligomer or oligomer obtained by the method of the present invention.

[0009] An object of the present invention is to provide an antiviral product comprising a purified 3-hydroxybutyrate oligomer or oligomer obtained by the method of the present invention.

[0010] To achieve the above object, the technical solution adopted by the present invention is as follows:

[0011] In one aspect, the present invention provides a method for separating and purifying a synthetic 3-hydroxybutyrate oligomer or oligomer, the method comprising the following steps:

[0012] A. Using a metal organic compound as a catalyst, synthesizing a 3-hydroxybutyrate oligomer or oligomer by ring-opening polymerization of lactone to obtain a mixed solution containing the metal organic compound catalyst and the 3-hydroxybutyrate oligomer or oligomer;

[0013] B. Adding a sufficient amount of organic acid to the mixed solution obtained in step A to form a solid precipitate, removing the solid precipitate by filtration, and collecting the filtrate;

[0014] C. Subjecting the filtrate obtained in step B to vacuum distillation at a temperature of 25°C to 120°C until no more organic liquid distills out;

[0015] D. Replacing the liquid-phase collector, gradually increasing the distillation temperature, collecting the fractions at a temperature of 121°C to 190°C until no more liquid phase distills out, thereby obtaining a purified 3-hydroxybutyrate oligomer or oligomer.

[0016] In one embodiment, the synthesis in step A is artificial synthesis.

[0017] In one embodiment, the metal organic compound used in step A is an organometallic complex containing one or more of aluminum, magnesium, titanium, zinc, and tin or containing rare earth elements, and the organometallic complex can react with the organic acid used in step B to form an insoluble precipitate.

[0018] In one embodiment, the organic acid used in step B is citric acid, citric acid hydrate, or any mixture thereof.

[0019] In one embodiment, the filtration treatment in step B is vacuum filtration, using diatomaceous earth as the filter aid and ethanol or isopropanol as the detergent for the diatomaceous earth.

[0020] In one embodiment, in step C, the temperature of the vacuum distillation is controlled at 25°C to 120°C, and the vacuum degree is controlled such that the vacuum gauge reading is equal to or less than -0.1 MPa.

[0021] In one embodiment, in step D, the fractions are collected by vacuum distillation, the temperature range is controlled at 121°C to 180°C, and the vacuum degree is controlled such that the vacuum gauge reading is equal to or less than -0.1 MPa.

[0022] In one embodiment, the weight-average molecular weight range of the purified 3-hydroxybutyrate oligomer or oligomers is 300 to 1,000, and it is a colorless transparent oily liquid at normal temperature and pressure.

[0023] In another aspect, the present invention provides an antibacterial and / or antiviral product, which contains the purified 3-hydroxybutyrate oligomer or oligomers obtained by the method according to the present invention.

[0024] In one embodiment, the antibacterial and / or antiviral product exists in the form of powder, solution, sol, gel, fiber, yarn or film.

[0025] In one embodiment, the antibacterial and / or antiviral product is used as the sole active ingredient or one of the active ingredients in external coating materials, textiles, hygiene products, drug carriers, fabric finishing agents, softeners, washing and cleaning products or medical products.

[0026] The present invention has the following beneficial effects:

[0027] 1) The method is simple to operate, low in cost, and does not require special equipment;

[0028] 2) The raw materials are widely sourced, and the required reagents can be easily obtained;

[0029] 3) It does not involve the use of toxic and harmful chemicals, and is green, safe and non-toxic;

[0030] 4) It can be mass-produced repeatedly;

[0031] 5) The obtained product has good antibacterial and antiviral activities, and has good cell compatibility, and can be used alone or in combination in the biomedical industry;

[0032] 6) It is environmentally friendly and can be naturally hydrolyzed and degraded without polluting the water body. Description of the Drawings

[0033] Figure 1 It is a high performance liquid chromatography - mass spectrometry combined spectrogram of the purified 3 - hydroxybutyrate oligomer or oligomer obtained according to Example 1 of the present invention, using acetonitrile as the mobile phase, where β - butyrolactone: β - butyrolactone; Aluminum Citrate: aluminum citrate; Aluminum Isopropoxide: aluminum isopropoxide; Citrate: citric acid.

[0034] Figure 2 It is a Fourier transform infrared spectrogram of the sample obtained by the potassium bromide tablet pressing method for the purified 3 - hydroxybutyrate oligomer or oligomer obtained according to Example 2 of the present invention.

[0035] Figure 3 It is a nuclear magnetic resonance (hydrogen - 1) spectrogram of the purified 3 - hydroxybutyrate oligomer or oligomer obtained according to Example 2 of the present invention.

[0036] Figure 4 It is a nuclear magnetic resonance (carbon - 13) spectrogram of the purified 3 - hydroxybutyrate oligomer or oligomer obtained according to Example 2 of the present invention.

[0037] Figure 5 It is a digital photo of the antibacterial experiment results of the purified 3 - hydroxybutyrate oligomer or oligomer obtained according to Example 1 of the present invention, and the test bacterial strain is Staphylococcus aureus. Detailed Description of the Invention

[0038] One aspect of the present invention relates to a method for separating and purifying a synthetic 3 - hydroxybutyrate oligomer or oligomer, and the method includes the following steps:

[0039] A. Using a metal - organic compound as a catalyst, synthesizing a 3 - hydroxybutyrate oligomer or oligomer through ring - opening polymerization of lactone to obtain a mixed solution containing the metal - organic compound catalyst and the 3 - hydroxybutyrate oligomer or oligomer;

[0040] B. Adding a sufficient amount of organic acid to the mixed solution obtained in step A to form a solid precipitate, removing the solid precipitate through filtration, and collecting the filtrate;

[0041] C. Subjecting the filtrate obtained in step B to vacuum distillation at a temperature of 25°C to 120°C until no more organic liquid distills out;

[0042] D. Replace the liquid-phase collector, gradually increase the distillation temperature, and collect the fractions at a temperature of 121°C to 190°C until no more liquid phase distills out, thereby obtaining purified 3-hydroxybutyrate oligomers or oligomers.

[0043] In one embodiment, the purified 3-hydroxybutyrate oligomers or oligomers have the following structural formula:

[0044] Wherein, n = 2 - 10, preferably n = 4 - 8.

[0045] In one embodiment, the weight-average molecular weight range of the purified 3-hydroxybutyrate oligomers or oligomers is 300 - 1,000, and it is a colorless transparent oily liquid at normal temperature and pressure.

[0046] In one embodiment, the synthesis in step A is artificial synthesis. In one embodiment, β-butyrolactone is used as the lactone ring-opening polymerization monomer.

[0047] In one embodiment, the organometallic compound catalyst is an organometallic complex containing one or more of aluminum, magnesium, titanium, zinc, or tin or containing rare earth elements, and this organometallic complex can react with organic acids to form insoluble precipitates. In one embodiment, the organometallic compound catalyst is an aluminum alkoxide, preferably C 1-6 aluminum alkoxide, more preferably aluminum isopropoxide.

[0048] In one embodiment, β-butyrolactone is used as the lactone ring-opening polymerization monomer, and aluminum isopropoxide is used as the catalyst, and the reaction is carried out in the presence of pyridine to obtain 3-hydroxybutyrate oligomers or oligomers.

[0049] In one embodiment, step B is to convert the organometallic compound catalyst into a solid precipitate by adding an excessive amount of organic acid, and then remove this solid precipitate from the solution by filtration treatment.

[0050] In one embodiment, the organic acid is any organic acid that can react with the organometallic compound to form an insoluble metal organic acid solid precipitate. In one embodiment, the organic acid is citric acid. In one embodiment, the organic acid is one or any mixture of citric acid and citric acid hydrate. In one embodiment, the organic acid is dissolved in a low-boiling organic solvent to make a precipitating agent solution. In one embodiment, the precipitating agent solution is a room-temperature saturated solution of citric acid. In one embodiment, the low-boiling organic solvent is ethanol, isopropanol, n-propanol, or a combination thereof.

[0051] In one embodiment, the filtration treatment in step B is carried out by reduced-pressure filtration. In one embodiment, during the filtration treatment, diatomaceous earth is used as a filter aid. In one embodiment, during the reduced-pressure filtration treatment, diatomaceous earth is used as a filter aid, and a low-boiling organic solvent, preferably the same solvent as the organic solvent for dissolving the organic acid, such as ethanol or isopropanol, etc., is used as a detergent to elute the diatomaceous earth.

[0052] In one embodiment, step C is to remove low-boiling organic components in the polymerization reaction mixture by reduced-pressure distillation, for example, ethanol, isopropanol, unreacted components, by-products, etc. In step C, the temperature of the reduced-pressure distillation is controlled at 25°C to 120°C, preferably 60 - 120°C, more preferably 80 - 120°C, even more preferably 100 - 120°C, and the vacuum degree is controlled such that the vacuum gauge reading is equal to or less than -0.1 MPa.

[0053] In one embodiment, step D is to obtain purified 3-hydroxybutyrate oligomers or oligomers from the solution by reduced-pressure distillation. In a further embodiment, in step D, the temperature range of the reduced-pressure distillation is controlled at 121°C to 190°C, preferably 130°C to 180°C, more preferably 140°C to 160°C; the vacuum degree is controlled such that the vacuum gauge reading is equal to or less than -0.1 MPa.

[0054] The method of the present invention separates and purifies 3-hydroxybutyrate oligomers or oligomers from the synthetic reaction mixed solution by combining precipitation, filtration, and distillation. The method of the present invention is simple to operate, the raw materials and reagents used are widely sourced and inexpensive, and it does not involve the use of any toxic or harmful chemicals. Therefore, it is a green, safe, non-toxic, cost-controllable, and large-scale production method.

[0055] The purified 3-hydroxybutyrate oligomers or oligomers obtained by the method of the present invention can maintain good cell compatibility and biodegradability.

[0056] The purified 3-hydroxybutyrate oligomers or oligomers obtained by the method of the present invention have good antibacterial and antiviral activities and can be used as antibacterial agents and / or antiviral agents in the fields of biomedicine, textile and clothing, food packaging, and medical and health care, etc.

[0057] Another aspect of the present invention relates to an antibacterial product, which comprises the purified 3-hydroxybutyrate oligomers or oligomers obtained by the method of the present invention.

[0058] In one embodiment of the present invention, the antimicrobial article comprises a purified 3-hydroxybutyrate oligomer or oligomers obtained by the method of the present invention as the sole antimicrobial active component. In one embodiment of the present invention, the antimicrobial article comprises a purified 3-hydroxybutyrate oligomer or oligomers obtained by the method of the present invention and an additional antimicrobial active component. In one embodiment, the additional antimicrobial active components include, but are not limited to, ethanol, lactic acid, acetic acid, citric acid, gallic acid, triclosan or chloroxylenol.

[0059] In one embodiment, the antimicrobial article comprises a product obtained by compounding or copolymerizing a 3-hydroxybutyrate oligomer or oligomers obtained by the method of the present invention with other polymer components. In one embodiment, the other polymer components include, but are not limited to, polylactic acid or PET-based polyesters.

[0060] In one embodiment, the antimicrobial article is in the form of a powder, solution, sol, gel, fiber, yarn or film.

[0061] In one embodiment, the antimicrobial article can be used as the sole active component or one of the active components in textiles, outer coating materials, hygiene products, drug carriers, fabric finishing agents, washing and cleaning products or medical articles, etc.

[0062] Another aspect of the present invention relates to an antiviral article which comprises a purified 3-hydroxybutyrate oligomer or oligomers obtained by the method of the present invention.

[0063] In one embodiment of the present invention, the antiviral article comprises a purified 3-hydroxybutyrate oligomer or oligomers obtained by the method of the present invention as the sole antiviral active component. In one embodiment of the present invention, the antiviral article comprises a purified 3-hydroxybutyrate oligomer or oligomers obtained by the method of the present invention and an additional antiviral active component. In one embodiment, the additional antiviral active components include, but are not limited to, gallic acid, triclosan or chloroxylenol.

[0064] In one embodiment, the antiviral article comprises a product obtained by compounding or copolymerizing a purified 3-hydroxybutyrate oligomer or oligomers obtained by the method of the present invention with other polymer components. In one embodiment, the other polymer components include, but are not limited to, polylactic acid or PET-based polyesters.

[0065] In one embodiment, the antiviral article is in the form of a powder, solution, sol, gel, fiber, yarn or film.

[0066] In one embodiment, the antiviral article can be used as the sole active component or one of the active components in textiles, outer coating materials, hygiene products, drug carriers, fabric finishing agents, washing and cleaning products or medical articles, etc.

[0067] Example

[0068] The following examples are only for the purpose of illustrating certain aspects and embodiments of the present invention, and are not intended to limit the present invention in any way.

[0069] Example 1

[0070] 1) Synthesize 3-hydroxybutyrate oligomers or oligomers

[0071] In an anhydrous and anaerobic glove box, 0.86 g of β-butyrolactone was weighed as the ring-opening polymerization monomer, 0.2 g of aluminum isopropoxide was weighed as the catalyst, and 2 mL of pyridine were added to a single-neck round-bottom glass flask. A polytetrafluoroethylene magnetic stirrer was added, sealed, and nitrogen was introduced to remove the air inside, and a certain nitrogen pressure was maintained during the reaction to provide an inert atmosphere protection. The single-neck glass flask containing the reactants was placed in an oil bath at 65 °C and reacted under constant temperature stirring for 48 hours until the color of the reactants turned brownish, obtaining the crude reaction product.

[0072] 2) Separate and remove the catalyst solid by organic acid precipitation method

[0073] In an anhydrous and anaerobic glove box, 0.3 g of solid citric acid monohydrate was weighed and added to 10 mL of ethanol. It was strongly stirred until completely dissolved to prepare a precipitant solution. The precipitant solution was added dropwise to the crude product prepared in step 1), and magnetically stirred for 2 hours until the yellowish-white precipitation reaction was complete. Then, using the diatomite filtration method, the reaction mixture was quickly filtered through a Buchner funnel to remove impurities such as solid catalysts, and rinsed repeatedly with ethanol 2-3 times. The filtrate was collected in a single-neck glass flask.

[0074] 3) Remove low-boiling organic liquid components

[0075] Using a vacuum distillation device with a straight glass condenser, evacuate to a vacuum gauge reading of -0.1 MPa. The filtrate of the reaction mixture obtained in step 2) was heated to 120 °C using a high-temperature oil bath magnetic stirrer, and the distillate at this temperature was collected until no more distillate was distilled out.

[0076] 4) Temperature gradient vacuum fractionation of liquid-phase 3-hydroxybutyrate oligomers or oligomers

[0077] Replace the receiving flask, use the vacuum distillation device in step 3), with a vacuum gauge reading of -0.1 MPa. Gradually heat the oil bath to 140 °C, collect the distillate at 140 °C until no more distillate is distilled out. The collected sample is a nearly colorless and transparent liquid.

[0078] 5) High performance liquid chromatography-mass spectrometry (HPLC-MS) test

[0079] For the fractions collected in step 4), an Agilent 6460 Ultra High Performance Liquid Chromatography / Electrospray Ionization Triple-Quadrupole Mass Spectrometer was used to test the composition of the relevant fractions, and the mobile phase used was chromatographically pure acetonitrile.

[0080] The obtained spectrogram is shown in Figure 1 . The molecular weight distribution of the separated main product is in the range of 300 - 1000. In addition, there are also a small amount of unreacted reactant monomers, citric acid, catalyst, etc.

[0081] Example 2

[0082] The same method as in steps 1) to 4) of Example 1 was used for separation and purification, but the differences are as follows:

[0083] 1) Precipitant

[0084] Anhydrous citric acid was used.

[0085] 2) Citric acid solvent and diatomite eluent

[0086] Isopropanol was used to replace ethanol to dissolve citric acid and elute diatomite.

[0087] 3) Temperature for collecting fractions

[0088] Fractions at 160 °C were collected.

[0089] The fractions collected in step 4) were tested for Fourier transform infrared absorption spectrum of the collected samples by the potassium bromide tablet method using a PerkinElmer Spectrum100 FT-IR Spectrometer. The spectrogram is shown in Figure 2 . The absorption peak at a wavenumber of ~3400 cm -1 is the molecular vibration absorption peak of the hydroxyl groups of the 3-hydroxybutyrate oligomers or oligomers and the hydroxyl group of the carboxylic acid. The three medium-intensity characteristic absorption peaks at a wavenumber of ~3000 cm -1 correspond to the stretching vibration absorption peaks of methyl C-H, secondary C-C-H, and tertiary C-C-H of the 3-hydroxybutyrate oligomers or oligomers respectively. The sharp peak at a wavenumber of ~1700 cm -1 is the carbonyl stretching vibration absorption peak of the ester bond contained in the 3-hydroxybutyrate oligomers or oligomers.

[0090] An appropriate amount of the fractions collected in step 4) was dissolved in deuterated chloroform (CDCl3) solvent, and 1H nuclear magnetic resonance spectrum was obtained by nuclear magnetic resonance (1 H-NMR) (as Figure 3 shown) and carbon-13 nuclear magnetic resonance ( 13 C-NMR) (as Figure 4 shown), confirming the obtaining of 3-hydroxybutyrate oligomers.

[0091] Activity test section

[0092] Example 3

[0093] 1) Prepare a sterilized Lubria-Bertani (L-B) liquid bacterial culture medium containing the 3-hydroxybutyrate oligomers obtained through steps 1) to 4) of Example 1, where the concentration of the 3-hydroxybutyrate oligomers is 20 mg / mL, as the experimental group; the blank control group uses a sterilized L-B bacterial culture medium without 3-hydroxybutyrate oligomers but with the same other components.

[0094] 2) Use Staphylococcus aureus (S. aureus ATCC No. 6538) as the experimental bacteria for Gram-positive bacteria, and inoculate the bacteria into the experimental group and control group L-B liquid bacterial culture media in step 1) of the experiment respectively. According to the ASTM standard, control the concentration of the inoculated bacteria at 10 5 CFU / mL.

[0095] 3) Incubate the two groups of experimental samples inoculated in the above step 2) in a constant-temperature bacterial shaker at 24 °C for 18 hours, then take samples, dilute them with a sterile PBS buffer solution, spread them on plates, and incubate them in a constant-temperature incubator at 37 °C for 18 - 48 hours, and then take them out to observe the growth of the colonies to be tested.

[0096] The results are shown in Figure 5 , where the left figure is the blank control group without 3-hydroxybutyrate oligomers, and the right figure is the experimental group containing 3-hydroxybutyrate oligomers. The Staphylococcus aureus in the blank experimental group grows normally, while no obvious Staphylococcus aureus colonies are seen in the experimental group containing 3-hydroxybutyrate oligomers, thus indicating that the 3-hydroxybutyrate oligomers separated and purified by the method of the present invention have obvious antibacterial activity.

[0097] Example 4

[0098] The experimental samples of 3-hydroxybutyrate oligomers obtained through steps 1) to 4) of Example 1 were delivered to the Guangdong Microbial Analysis and Testing Center for antiviral experiment-related tests against two influenza viruses, H1N1 and H3N2. MDCK cells were used as host cells in this experiment. The experimental method referred to "Disinfection Technical Specification" (2002 Edition) 2.1.1.10.7 issued by the Ministry of Health of the People's Republic of China.

[0099] The experimental results of the antiviral test are shown in the following table:

[0100]

[0101] * All cells in the negative control group grew well.

[0102] The experimental results report of the antiviral test showed that when the concentration of 3-hydroxybutyrate oligomers was 20 mg / mL, for H1N1 and H3N2 influenza viruses, the lgTCID 50 / mL values of the experimental samples of 3-hydroxybutyrate oligomers were both less than 1.50, while the average lgTCID 50 / mL values of the experimental control groups under the same conditions were 5.74 and 5.90 respectively. It can be seen from this that the antiviral activity rates of the 3-hydroxybutyrate oligomers isolated and purified by the method of the present invention against H1N1 and H3N2 influenza viruses were both >99.99%. The above experimental results indicate that the 3-hydroxybutyrate oligomers isolated and purified by the method of the present invention have obvious antiviral activity.

[0103] Although the present invention has been described with reference to specific embodiments of the present invention, those skilled in the art should understand that various changes and modifications can be made without departing from the true spirit and scope of the present invention. In addition, many modifications can be made to adapt a particular situation, material, composition of matter, method, and method step to the spirit and scope of the present invention. All such changes will fall within the scope of the appended claims.

Claims

1. A method for separating and purifying synthetic 3-hydroxybutyrate oligomers or oligomers, characterized in that, The method comprises the following steps: A. Using a metal-organic compound as a catalyst, synthesizing 3-hydroxybutyrate oligomers or oligomers through ring-opening polymerization of lactone to obtain a mixed solution containing the metal-organic compound catalyst and 3-hydroxybutyrate oligomers or oligomers; B. Adding a sufficient amount of organic acid to the mixed solution obtained in step A to generate a solid precipitate, removing the solid precipitate through filtration, and collecting the filtrate; C. Subjecting the filtrate obtained in step B to vacuum distillation at a temperature of 25°C to 120°C until no more organic liquid distills out; D. Replacing the liquid-phase collector, gradually increasing the distillation temperature, collecting the fractions at a temperature of 121°C to 190°C until no more liquid phase distills out, thereby obtaining purified 3-hydroxybutyrate oligomers or oligomers, wherein the purified 3-hydroxybutyrate oligomers or oligomers have the following structural formula: wherein, n = 2 - 10; wherein the metal-organic compound is an organometallic complex containing one or more of aluminum, magnesium, titanium, zinc, and tin or containing rare earth elements, and the organometallic complex can react with the organic acid to form an insoluble precipitate; and wherein the organic acid is citric acid, citric acid hydrate, or any mixture thereof.

2. The method according to claim 1, wherein: The synthesis in step A is a synthetic process.

3. The method according to claim 1, characterized in that: The filtration treatment in step B is vacuum filtration, using diatomaceous earth as a filter aid and ethanol or isopropanol as a detergent for the diatomaceous earth.

4. The method according to claim 1, wherein: In step C, the temperature of the vacuum distillation is controlled at 25°C to 120°C, and the vacuum degree is controlled such that the vacuum gauge reading is equal to or less than -0.1 MPa.

5. The method according to claim 1, wherein: In step D, the fractions are collected through vacuum distillation, the temperature range is controlled at 121°C to 180°C, and the vacuum degree is controlled such that the vacuum gauge reading is equal to or less than -0.1 MPa.

6. The method according to any one of claims 1 to 5, characterized in that: The weight-average molecular weight range of the purified 3-hydroxybutyrate oligomers or oligomers is 300 to 1,000, and it is a colorless transparent oily liquid at normal temperature and pressure.

7. An antiviral product, characterized in that, The antiviral product contains the purified 3-hydroxybutyrate oligomers or oligomers obtained by the method according to any one of claims 1 to 6 as an antiviral active component.

8. An antibacterial and antiviral product, characterized in that, The antibacterial and antiviral product contains the purified 3-hydroxybutyrate oligomers or oligomers obtained by the method according to any one of claims 1 to 6 as an antibacterial and antiviral active component.

9. The article according to any one of claims 7 to 8, characterized in that, The product exists in the form of powder, solution, sol, gel, fiber, yarn, or film.

10. The article according to claim 9, characterized in that, The product is used as the sole active component or one of the active components in external coating materials, textiles, sanitary products, fabric finishing agents, fabric softeners, washing and cleaning products, or medical products.

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