CN111333778A - Waterproof polymer bactericide and preparation method and application thereof - Google Patents
Waterproof polymer bactericide and preparation method and application thereof Download PDFInfo
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- CN111333778A CN111333778A CN202010198099.6A CN202010198099A CN111333778A CN 111333778 A CN111333778 A CN 111333778A CN 202010198099 A CN202010198099 A CN 202010198099A CN 111333778 A CN111333778 A CN 111333778A
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- water
- bactericide
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- 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
- C08F226/10—N-Vinyl-pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
- A61K31/787—Polymers containing nitrogen containing heterocyclic rings having nitrogen as a ring hetero atom
- A61K31/79—Polymers of vinyl pyrrolidone
-
- 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
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—Monomers containing five or more carbon atoms
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
- C08F8/22—Halogenation by reaction with free halogens
Abstract
The invention belongs to the technical field of medicines, and discloses a waterproof polymer bactericide, and a preparation method and application thereof.
Description
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to a waterproof polymer bactericide as well as a preparation method and application thereof.
Background
At present, medical iodophor, povidone iodine and the like are adopted for skin wound rupture of a human body to be disinfected and then bound by clean gauze, or directly protected by adhesive such as a bromobenzene-bound wound plaster and the like. For the parts of human hands, faces and the like which are always in contact with water, wounds are easy to be stained with water to cause infection, because the bactericides are water-soluble and are easy to dissolve in water to lose the protection of the wounds, therefore, manufacturers provide a waterproof adhesive tape type wound plaster as a solution, the solution can completely isolate the wounds and the surrounding skin from the surrounding environment, so that infection is avoided, and the defect is that the air permeability is poor.
For artificially cultured aquatic animals or field-cherished aquatic animals, if trauma occurs, in order to prevent the loss of lives caused by infection with germs, several methods are frequently used for treatment, one is to feed antibiotics in a culture water area or carry out antibiotic bath on a single cylinder of the animals, but the antibiotics can generate drug resistance after long-term use; secondly, the wound is coated with the external bactericide, then the wound is subjected to medicated bath in a separate sterile water environment or in a low-concentration bactericide solution, and the wound is placed back to the original water area after healing. These methods are costly and subject to antibiotic abuse.
The main difficulty of the above problems is that the aforementioned bactericides such as iodophor, povidone iodine, and bromobenzazan are all water-soluble, cannot provide a bactericidal effect continuously in an environment with water, and currently, there are no reports on bactericides with water resistance.
Disclosure of Invention
In view of the above situation, the inventor of the present invention found that povidone-iodine is a common powerful broad-spectrum disinfectant, and has the advantages of good water solubility, low toxicity, small irritation to skin, lasting effect, safe and convenient use, and the like, povidone-iodine is a complex of polyvinylpyrrolidone and iodine, and has a certain film forming property and adhesion, α -olefin is an important organic raw material and an intermediate product, and has hydrophobicity, and since several straight-chain α -olefin polymers have the advantage of good biodegradability, α -olefin is widely applied in the fields of detergents, leather treatment agents, fabric finishing agents, lubricating oil, and the like.
The first aspect of the present invention provides a method for producing a water-repellent polymer bactericide, which comprises polymerizing N-vinylpyrrolidone with α -olefin, and complexing with refined iodine to produce the water-repellent polymer bactericide.
Preferably, the preparation method comprises:
(1) polymerization of N-vinylpyrrolidone with α -olefin
Mixing N-vinyl pyrrolidone and α -olefin according to the mass ratio of 10: 90-50: 50, reacting for 10-30 hours at the reaction temperature of 100 ℃ and 140 ℃ in the presence of a solvent and an initiator to obtain a viscous alkylated vinyl pyrrolidone polymer solution, and removing the solvent through reduced pressure distillation to obtain a liquid alkylated vinyl pyrrolidone polymer;
(2) complexation of alkylated vinylpyrrolidone polymers with refined iodine
And (2) mixing the alkylated vinyl pyrrolidone polymer obtained in the step (1) with refined iodine, stirring at 50-95 ℃, carrying out complex reaction for 4-18 hours, and cooling to room temperature to obtain the waterproof polymer bactericide.
In the present invention, the α -olefin may be C6-C18For example, α -olefin can be α -hexene, α -decene, α -hexadecene, α -octadecene, 3-methyl-1-hexene, and the like.
Preferably, the solvent is C5-C10Saturated hydrocarbons or C2-C10Monohydric alcohols of saturated hydrocarbons. Specific examples of the solvent include, but are not limited to: anhydrous ethanol, cyclohexane, n-butanol, and the like.
In the present invention, the mass ratio of the N-vinylpyrrolidone and α -olefin to the solvent may be 10: 90 to 90: 10, and preferably 30: 70 to 90: 10.
Preferably, the initiator is a peroxide initiator. Further preferably, the initiator is at least one of tert-butyl hydroperoxide, cumyl hydroperoxide and tert-butyl cumyl hydroperoxide.
According to the invention, the ratio of the mass of the initiator to the sum of the masses of the N-vinylpyrrolidone and α -olefin may be 1: 100 to 10: 100.
Preferably, in the step (1), the reaction temperature is 125-135 ℃, and the reaction time is 12-24 hours.
Preferably, the alkylated vinylpyrrolidone polymer has < 0.02% residual N-vinylpyrrolidone and < 0.5% residual solvent. The above residual substances were tested by gas chromatography external standard method.
According to the invention, in step (2), the amount of refined iodine added is 1-12%, preferably 6-10% of the mass of the N-vinylpyrrolidone monomer in the alkylated vinylpyrrolidone polymer.
Preferably, in step (2), the complexing reaction time is 10 to 15 hours.
The process parameters not defined in the present invention are carried out by conventional methods in the art, such as distillation under reduced pressure.
The second aspect of the present invention provides a water-repellent polymer bactericide obtained by the above-mentioned method for producing a water-repellent polymer bactericide.
The waterproof polymer bactericide prepared by the invention is a tan liquid polymer and has waterproof and bactericidal properties, wherein α -olefin groups are used for improving the waterproof property of the bactericide, N-vinyl pyrrolidone groups are beneficial to the complexation with iodine, and iodine elements provide bactericidal action.
A third aspect of the present invention provides the use of the above water-resistant polymer bactericide in skin disinfection or treatment of wounds of aquatic animals.
When in use, the waterproof polymer bactericide can be directly smeared on the skin or the surface of a wound, the waterproof duration can reach 12 hours, and the bactericidal effect can be kept in water for a long time.
The invention obtains the waterproof polymer bactericide by polymerizing the N-vinyl pyrrolidone and the α -olefin and then complexing with the iodine, and the α -olefin has more proportion in the polymer bactericide, so the polymer bactericide can provide excellent waterproof property and film forming property and simultaneously has the bactericidal property provided by iodine element, and the product is a novel product in the field of bactericides, can be used for treating human body wounds and aquatic animal wounds which need to be frequently contacted with water, and has good bactericidal effect, low irritation and good waterproof effect.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments.
Examples 1 to 6 are for illustrating the water-repellent polymer bactericide of the present invention, the production method and the application thereof.
Example 1
(1) α -hexene 80g, N-vinyl pyrrolidone 80g and absolute ethyl alcohol 160g are sequentially added into a high-pressure glass reaction kettle, after nitrogen gas replacement, when the temperature is raised to 130 ℃, tert-butyl hydroperoxide 1.6g is added through an adding device, the reaction temperature is controlled at 130 ℃ for 12 hours, then a vacuum valve is opened, the solvent is removed under reduced pressure for about 1 hour, and colorless transparent viscous polymer liquid is obtained, and the residual N-vinyl pyrrolidone is 0.018 percent and the ethyl alcohol is 0.03 percent according to a gas chromatography external standard method.
(2) And (2) sequentially adding 40g of the colorless polymer liquid sample prepared in the step (1) and 2g of refined iodine into a 100mL single-neck flask, stirring and sealing, controlling the temperature of a water bath kettle to be 50 ℃, and stirring and reacting for 15 hours. After cooling, a reddish brown liquid polymer (water-proof polymer bactericide) is obtained.
The prepared bactericide is tested for water resistance at 23 ℃ by using distilled water as a testing medium, and the result shows that the bactericide can effectively resist water for about 40 minutes; after contacting with bacteria for 10 minutes, 99.99 percent of gram-positive bacteria and gram-negative bacteria can be killed, and excellent sterilization efficiency is shown.
Example 2
(1) The preparation method comprises the following steps of sequentially adding 230g of α -hexadecene, 58g of N-vinyl pyrrolidone and 32g of absolute ethyl alcohol into a high-pressure glass reaction kettle, replacing nitrogen, heating to 135 ℃, adding 16g of cumyl hydroperoxide through an adding device, controlling the reaction temperature to react for 24 hours, then opening a vacuum valve, decompressing and removing a solvent for about 1 hour to obtain colorless transparent viscous polymer liquid, and testing the content of the residual N-vinyl pyrrolidone to be 0.012% and the content of the ethyl alcohol to be 0.07% through a gas chromatography external standard method.
(2) And (2) taking 50g of the colorless polymer liquid sample obtained in the step (1) and 0.6g of refined iodine, sequentially adding the sample and the refined iodine into a 100mL single-neck flask, installing, stirring and sealing, controlling the temperature of an oil bath kettle to be 95 ℃, stirring and reacting for 10 hours, and then cooling to room temperature to obtain the reddish brown flowable liquid polymer (the waterproof polymer bactericide).
At 23 ℃, distilled water and 3% sodium chloride solution are respectively used as testing media, and the prepared bactericide is tested for water resistance, and the result shows that the bactericide can effectively resist water for 2 hours; 99.78% of E.coli and 99.97% of S.aureus were killed after 10 minutes of exposure.
Example 3
(1) Adding 118g of α -hexadecene, 42g of N-vinyl pyrrolidone and 160g of cyclohexane into a high-pressure glass reaction kettle in sequence, after nitrogen replacement, heating to 130 ℃, adding 6g of tert-butyl hydroperoxide and 4g of cumyl hydroperoxide through an initiator feeder, controlling the reaction temperature to react for 18 hours, then opening a vacuum valve, decompressing and removing a solvent for about 2 hours to obtain light yellow transparent viscous polymer liquid, and testing the residual N-vinyl pyrrolidone to be 0.015% and the cyclohexane to be 0.13% through a gas chromatography external standard method.
(2) And (2) taking 50g of the light yellow polymer liquid sample prepared in the step (1) and 1.2g of refined iodine, sequentially adding the light yellow polymer liquid sample and the refined iodine into a 100mL single-neck flask, installing, stirring and sealing, controlling the temperature of a water bath kettle to be 70 ℃, stirring and reacting for 12 hours, and then cooling to room temperature to obtain the reddish brown liquid polymer (the waterproof polymer bactericide).
At 23 ℃, distilled water and 3% sodium chloride solution are respectively used as testing media to test the waterproofness, and the result shows that the waterproof effect can be effectively achieved for 8 hours; the bactericidal performance test result shows that: after 10min of bacterial contact, 96.8% of Escherichia coli and 99.7% of Staphylococcus aureus can be killed.
Example 4
(1) α -octadecane 86g, N-vinyl pyrrolidone 10g and N-butanol 224g are sequentially added into a high-pressure glass reaction kettle, after nitrogen replacement, when the temperature is raised to 135 ℃, tert-butyl cumyl hydroperoxide 9.6g is added through an adding device, the reaction temperature is controlled for 30 hours, then a vacuum valve is opened, the solvent is removed under reduced pressure for about 2 hours, and light yellow transparent viscous polymer liquid is obtained, the residual N-vinyl pyrrolidone of the liquid is 0.008 percent and the N-butanol of the liquid is 0.27 percent according to a gas chromatography external standard method.
(2) And (2) taking 60g of the light yellow polymer liquid sample prepared in the step (1) and 0.62g of refined iodine, sequentially adding the light yellow polymer liquid sample and the refined iodine into a 100mL single-neck flask, installing, stirring and sealing, controlling the temperature of an oil bath kettle to be 85 ℃, stirring and reacting for 15 hours, and then cooling to room temperature to obtain the reddish brown liquid polymer (the waterproof polymer bactericide).
At 23 ℃, distilled water and 3% sodium chloride solution are respectively used as testing media to test the waterproofness, and the result shows that the waterproof effect can be effectively achieved for more than 12 hours; the killing test of the finless eel breeding water source shows that the bactericide prepared by the scheme has good killing performance on the hydrophile monad, and the sterilizing rate can reach 99.99%.
Example 5
(1) α -hexene 80g, N-vinyl pyrrolidone 80g and absolute ethyl alcohol 160g are sequentially added into a high-pressure glass reaction kettle, after nitrogen gas replacement, when the temperature is raised to 130 ℃, tert-butyl hydroperoxide 1.6g is added through an adding device, the reaction temperature is controlled at 130 ℃ for 12 hours, then a vacuum valve is opened, the solvent is removed under reduced pressure for about 1 hour, and colorless transparent viscous polymer liquid is obtained, and the residual N-vinyl pyrrolidone is 0.018 percent and the ethyl alcohol is 0.03 percent according to a gas chromatography external standard method.
(2) And (2) sequentially adding 60g of the colorless polymer liquid sample prepared in the step (1) and 2.4g of refined iodine into a 100mL single-neck flask, installing, stirring and sealing, controlling the temperature of an oil bath kettle to be 90 ℃, stirring and reacting for 15 hours, and then cooling to room temperature to obtain the reddish brown liquid polymer (the waterproof polymer bactericide).
At 23 ℃, distilled water and 3% sodium chloride solution are respectively used as testing media to test the waterproofness, and the result shows that the waterproof effect can be effectively achieved for 48 minutes; the killing experiment on the tilapia culture water source shows that the bactericide prepared by the scheme has good killing performance on streptococcus agalactiae, and the sterilizing rate can reach 99.97%. And comparing the tilapia smeared with the bactericide at the wound with the tilapia without the wound, and finding that the tilapia without the wound dies in advance.
Example 6
(1) Adding 70g of 3-methyl-1-hexene, 85g of N-vinyl pyrrolidone and 160g of absolute ethyl alcohol into a high-pressure glass reaction kettle in sequence, replacing nitrogen, heating to 130 ℃, adding 7g of tert-butyl hydroperoxide through a feeder, and controlling the reaction temperature to react for 10 hours. Then, the vacuum valve was opened, and the solvent was removed under reduced pressure for about 1 hour to obtain a colorless transparent viscous polymer liquid. The residual N-vinyl pyrrolidone of the product and the ethanol of the product are respectively 0.008 percent and 0.15 percent according to a gas chromatography external standard method.
(2) And (2) taking 60g of the polymer liquid sample prepared in the step (1) and 2.9g of refined iodine, sealing and stirring in a 100mL single-neck flask, controlling the temperature of a water bath kettle to be 80 ℃, reacting for 15 hours, and cooling to obtain the reddish brown flowable polymer (the waterproof polymer bactericide).
The water resistance of the bactericide is tested by distilled water at 23 ℃, and the result shows that the bactericide can effectively resist water for 2.5 hours; the test of the killing performance of the pathogenic bacteria, namely the solitary bacteria, of the mariculture shows that 99.9 percent of the solitary bacteria can be killed within half an hour.
Through the tests on the water resistance and the bactericidal performance of the bactericide prepared in the embodiment, the bactericide has excellent water resistance, the water resistance duration can reach 40 minutes to 12 hours, and the bactericidal effect is kept in water. When the bactericide is used for treating wounds of tilapia, the bactericide can effectively sterilize.
Having described embodiments of the present invention, the foregoing description is intended to be exemplary, not exhaustive, and not limited to the disclosed embodiments. Many modifications and variations will be apparent to those of ordinary skill in the art without departing from the scope and spirit of the illustrated embodiments.
Claims (10)
1. A process for preparing the water-proof polymer disinfectant includes polymerizing N-vinyl pyrrolidone and α -olefin, and complexing with refined iodine.
2. The method for producing a water-repellent polymer bactericide as claimed in claim 1, characterized in that: the preparation method comprises the following steps:
(1) polymerization of N-vinylpyrrolidone with α -olefin
Mixing N-vinyl pyrrolidone and α -olefin according to the mass ratio of 10: 90-50: 50, reacting for 10-30 hours at the reaction temperature of 100 ℃ and 140 ℃ in the presence of a solvent and an initiator to obtain a viscous alkylated vinyl pyrrolidone polymer solution, and removing the solvent through reduced pressure distillation to obtain a liquid alkylated vinyl pyrrolidone polymer;
(2) complexation of alkylated vinylpyrrolidone polymers with refined iodine
And (2) mixing the alkylated vinyl pyrrolidone polymer obtained in the step (1) with refined iodine, stirring at 50-95 ℃, carrying out complex reaction for 4-18 hours, and cooling to room temperature to obtain the waterproof polymer bactericide.
3. The method for producing a water-repellent polymer bactericide as claimed in claim 1 or 2, wherein said α -olefin is C6-C18Linear or branched olefins.
4. The method for producing a water-repellent polymer bactericide as claimed in claim 2, characterized in that: the solvent is C5-C10Saturated hydrocarbons or C2-C10Monohydric alcohols of saturated hydrocarbons;
the mass ratio of the N-vinylpyrrolidone and α -olefin to the solvent is 10: 90-90: 10.
5. The method for producing a water-repellent polymer bactericide as claimed in claim 2, characterized in that: the initiator is a peroxide initiator, and the peroxide initiator is at least one selected from tert-butyl hydroperoxide, cumyl hydroperoxide and tert-butyl cumyl hydroperoxide;
the mass ratio of the initiator to the sum of the masses of the N-vinylpyrrolidone and the α -olefin is 1: 100 to 10: 100.
6. The method for producing a water-repellent polymer bactericide as claimed in claim 2, characterized in that: in the step (1), the reaction temperature is 125-135 ℃, and the reaction time is 12-24 hours.
7. The method for producing a water-repellent polymer bactericide as claimed in claim 2, characterized in that: in the alkylated vinylpyrrolidone polymer, the residual N-vinylpyrrolidone is less than 0.02%, and the residual solvent is less than 0.5%.
8. The method for producing a water-repellent polymer bactericide as claimed in claim 2, characterized in that: in the step (2), the adding amount of the refined iodine is 1-12% of the mass of the N-vinyl pyrrolidone monomer in the alkylated vinyl pyrrolidone polymer; the complexing reaction time is 10-15 hours.
9. A water-repellent polymer bactericide produced by the method for producing a water-repellent polymer bactericide according to any one of claims 1 to 8.
10. Use of the water-resistant polymer bactericide of claim 9 for skin disinfection or treatment of wounds of aquatic animals.
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| CN202010198099.6A CN111333778A (en) | 2020-03-20 | 2020-03-20 | Waterproof polymer bactericide and preparation method and application thereof |
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| CN202010198099.6A CN111333778A (en) | 2020-03-20 | 2020-03-20 | Waterproof polymer bactericide and preparation method and application thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115216036A (en) * | 2022-07-27 | 2022-10-21 | 威海恒瑞新型包装材料有限公司 | Composite material for self-adhesive film and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA887143A (en) * | 1971-11-30 | Freifeld Milton | Halogen adduct of alkylated heterocyclic n-vinyl polymers | |
| CN107236087A (en) * | 2017-07-10 | 2017-10-10 | 上海宇昂水性新材料科技股份有限公司 | The preparation method and VP/ alpha olefin copolymers of VP/ alpha olefin copolymers |
| CN108219066A (en) * | 2018-01-11 | 2018-06-29 | 东莞理工学院 | A kind of nanometer of povidone-iodine antibacterial dyestuff and preparation method thereof |
-
2020
- 2020-03-20 CN CN202010198099.6A patent/CN111333778A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA887143A (en) * | 1971-11-30 | Freifeld Milton | Halogen adduct of alkylated heterocyclic n-vinyl polymers | |
| CN107236087A (en) * | 2017-07-10 | 2017-10-10 | 上海宇昂水性新材料科技股份有限公司 | The preparation method and VP/ alpha olefin copolymers of VP/ alpha olefin copolymers |
| CN108219066A (en) * | 2018-01-11 | 2018-06-29 | 东莞理工学院 | A kind of nanometer of povidone-iodine antibacterial dyestuff and preparation method thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115216036A (en) * | 2022-07-27 | 2022-10-21 | 威海恒瑞新型包装材料有限公司 | Composite material for self-adhesive film and preparation method thereof |
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