CN111621117A - Degradable polypropylene antibacterial material and preparation method thereof - Google Patents
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- C08F2438/00—Living radical polymerisation
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Abstract
The invention discloses a degradable polypropylene antibacterial material and a preparation method thereof; the degradable polypropylene antibacterial material mainly comprises degradable polypropylene, polymethacrylic acid block copolymer (PP-b-PMAA) and degradable polypropylene grafted sericin copolymer, and overcomes the defect that the common polypropylene non-woven fabric is not degradable; meanwhile, sericin has good antibacterial performance, a molecular chain contains a large number of active groups such as amino, hydroxyl, carboxyl and the like, and when the degradable polypropylene grafted sericin copolymer is blended with PP-b-PMAA, intermolecular hydrogen bond action exists between the two copolymers, so that the two block polymers have good compatibility.
Description
Technical Field
The invention belongs to the field of high polymer chemical synthesis, and particularly relates to a degradable polypropylene antibacterial material and a preparation method thereof.
Background
Sericin is a natural high molecular protein, and is abundant in resources; the sericin has excellent hydrophilicity and chemical activity, good hygroscopicity and the like on skin, has a series of unique biological properties such as oxidation resistance, bacteriostasis and the like, also has good biocompatibility and fluorescence, consists of eighteen amino acids such as serine, aspartic acid and the like, contains a large number of amino, hydroxyl, carboxyl and other active groups which are convenient to crosslink and modify, and is an excellent natural biological material.
The polypropylene fiber has the advantages of rich raw materials, low production cost, light weight, high strength, good wear resistance and elasticity, good hot melt property, excellent ultrasonic welding property, low price and the like, the polypropylene also has the advantage of relatively stable chemical property, the moisture absorption rate of the fiber material is zero, and the prepared melt-blown non-woven fabric has the characteristics of acid and alkali resistance, organic chemical solvent resistance, worm damage resistance, mildew and rot resistance, no toxicity and the like, and is suitable for environments under various conditions.
However, polypropylene has no antibacterial property and poor degradability, and along with the increasing use amount of disposable nonwoven polypropylene products, the problem of garbage pollution of disposable nonwoven polypropylene products is more and more serious, for example, CN105694229B discloses a PP antibacterial plastic and a preparation method thereof, wherein the antibacterial plastic is prepared from the following components in parts by weight: 100 parts of polypropylene, 3-5 parts of dodecyl trimethyl ammonium chloride, 2-5 parts of chitosan, 2-5 parts of betaine, 2-5 parts of nano zinc oxide powder, 3-5 parts of nano calcium oxide, 0.5-2 parts of zinc stearate, 0.5-2 parts of white oil, 0.5-5 parts of coupling agent, 0.5-2 parts of nonylphenol polyoxyethylene ether, 0.1-1 part of ethylene-octene copolymer, 0.5-1 part of antioxidant, 0.1-3 parts of random copolymer of styrene and maleic anhydride and 0.5-2 parts of plasticizer. The invention patent adds inorganic antibacterial substance into polypropylene base material by physical mixing method, because there is no chemical bond between inorganic antibacterial molecule and polypropylene base material, the uniformity of antibacterial agent is not easy to be guaranteed, besides, it is difficult to avoid the loss problem of antibacterial component, and it directly affects the long-term antibacterial performance of product. In addition, the prepared PP antibacterial plastic has the problem of environmental pollution. Based on the statement, the invention provides a degradable polypropylene antibacterial material and a preparation method thereof.
Disclosure of Invention
In order to solve the defects of the prior art, the invention provides a degradable polypropylene antibacterial material and a preparation method thereof, the degradable polypropylene antibacterial material mainly comprises degradable polypropylene, polymethacrylic acid block copolymer (PP-b-PMAA) and degradable polypropylene graft sericin copolymer, and the prepared degradable polypropylene antibacterial material overcomes the defect that common polypropylene non-woven fabrics are not degradable; meanwhile, sericin has good antibacterial performance, a molecular chain contains a large number of active groups such as amino, hydroxyl, carboxyl and the like, and when the degradable polypropylene grafted sericin copolymer is blended with PP-b-PMAA, intermolecular hydrogen bond action exists between the two copolymers, so that the two block polymers have good compatibility.
The invention aims to provide a degradable polypropylene antibacterial material.
The invention also aims to provide a preparation method of the degradable polypropylene antibacterial material.
The above purpose of the invention is realized by the following technical scheme:
the preparation method of the degradable polypropylene antibacterial material comprises the following steps:
the degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA) and the degradable polypropylene grafted sericin copolymer are prepared, wherein the degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA) accounts for 100 parts by weight, the degradable polypropylene grafted sericin copolymer accounts for 100 parts by weight, the nano calcium carbonate accounts for 20 parts by weight, the ethylene-1-octene copolymer accounts for 10 parts by weight, the polyvinyl alcohol accounts for 1 part by weight, the (2, 4-di-tert-butylphenyl) phosphite triester accounts for 0.5 part by weight, and the 2-hydroxy-4-methoxydiphenylacetone accounts for 0.5 part by weight in a high-speed mixer, and the mixed raw materials are placed in a parallel twin-screw extruder to be subjected to melt extrusion and granulation to prepare the degradable polypropylene antibacterial material.
The degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA) has a structural formula shown as the following formula (I):
wherein n is 20-100, and m is 100-1000.
The preparation method of the degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA) comprises the following steps:
1. and (3) preparing a polypropylene macromolecular chain transfer agent.
Toluene is used as a solvent, pyridine is used as an acid-binding agent, an RAFT reagent 4-cyano-4- (thiobenzoic acid) valeric acid is subjected to amidation reaction, and then the amidation reaction and single-end hydroxyl polypropylene are subjected to esterification reaction to obtain the polypropylene macromolecule transfer agent, wherein the molar ratio of the 4-cyano-4- (thiobenzoic acid) valeric acid to the single-end hydroxyl polypropylene is 4: 1.
2. And (3) preparing a degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA).
The preparation method comprises the steps of taking N, N-dimethylformamide DMF as a solvent, azodiisobutyronitrile as an initiator, a polypropylene macromolecular chain transfer agent as a chain transfer agent and methacrylic acid as monomers, reacting for 10-12 hours at 60-70 ℃ under the protection of oil bath nitrogen, and purifying to obtain PP-b-PMAA, wherein the molar ratio of the azodiisobutyronitrile to the polypropylene macromolecular chain transfer agent as a chain transfer agent to the methacrylic acid is 1:3:800, and the molar concentration of the methacrylic acid is 2 mol/L.
The preparation method of the degradable polypropylene grafted sericin copolymer comprises the following steps:
1. preparation of single-terminal hydroxyl polyacrylic chloride.
N2Under protection, using toluene as a solvent, carrying out acyl chlorination reaction on single-terminal hydroxyl polypropylene and succinyl chloride as raw materials, carrying out reflux reaction at 140 ℃ for 9 hours, treating with anhydrous acetone after the reaction is finished, and drying to obtain a polypropylene product with an acyl chloride group at the terminal, wherein the molar ratio of the single-terminal hydroxyl polypropylene to the succinyl chloride is 1: 300.
2. And (3) preparing the degradable polypropylene grafted sericin copolymer.
Taking dioxane as a solvent, taking a single-end hydroxyl polyacrylic chloride product and sericin as raw materials, reacting for 8 hours at 105 ℃, and saturating Na2CO3Neutralizing the reaction solution to obtain the degradable polypropylene grafted sericin copolymer, wherein the mass ratio of the single-end hydroxyl polyacryl chlorination product to the sericin is 1: 50.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the prepared degradable polypropylene antibacterial material mainly comprises degradable polypropylene, polymethacrylic acid block copolymer (PP-b-PMAA) and degradable polypropylene grafted sericin copolymer, and overcomes the defect that common polypropylene non-woven fabrics are not degradable.
(2) In the degradable polypropylene grafted sericin copolymer, sericin has good antibacterial performance, a molecular chain contains a large number of active groups such as amino, hydroxyl, carboxyl and the like, and when the degradable polypropylene grafted sericin copolymer is blended with PP-b-PMAA, intermolecular hydrogen bonding action exists between the two copolymers, so that the two block polymers have good compatibility.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum diagram of a degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA).
Detailed Description
The present invention will be described in further detail with reference to specific examples, which are not intended to limit the present invention in any manner. Reagents, methods and apparatus used in the present invention are conventional in the art unless otherwise indicated.
Example 1
And (3) preparing a degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA).
1) And (3) preparing a polypropylene macromolecular chain transfer agent.
RAFT reagent 4-cyano-4- (thiobenzoic acid) pentanoic acid (1.62g,4.0mmol) and 20ml anhydrous tetrahydrofuran THF are added to the reactor, after the reaction temperature is raised to 70 ℃, SOCl is slowly added dropwise2(2.9ml,4.0mmol), reaction for 2h after dropwise addition, after completion of the reaction, SOCl was removed by distillation under reduced pressure2And THF to give 4-cyano-4- (thiobenzoic acid) pentanoic acid acylchloride, which was dissolved in an appropriate amount of toluene.
Single-terminal hydroxyl Polypropylene PP-OH (0.84g,1.0mmol) was charged into a 50ml Schlenk bottle, and after purging with nitrogen three times, N2Under protection, 30ml of anhydrous toluene is added into a disposable syringe, the temperature is raised to 70 ℃, 1ml of pyridine is injected after PP-OH is completely dissolved, the mixture is stirred for 30min, the 4-cyano-4- (thiobenzoic acid) valeric acid acyl chloride product is dripped, the temperature is raised to 80 ℃, the reaction is continued for 2.5h, the product is cooled to room temperature, the mixture is continuously dissolved/precipitated twice by toluene/methanol, and then is dried to constant weight under vacuum at 45 ℃, so that 1.80g of polypropylene macromolecule transfer agent is obtained, and the yield is 73.2%.
2) And (3) preparing a degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA).
Methacrylic acid (1.3774g,16.0mmol), a polypropylene macromolecular chain transfer agent (0.0672g,0.06mmol) and azobisisobutyronitrile (0.0033g,0.02mmol) were charged into a 50ml Schlenk bottle, and after three nitrogen gas purges, N was added2Under protection, 20mL of N, N-dimethylformamide DMF is added by a disposable syringe, the mixture reacts for 10h under 70 ℃ oil bath, the mixture is put into liquid nitrogen to quench the product to stop the reaction, methanol/water is used as a precipitator, the precipitation is repeated for 3 times, and the mixture is dried under vacuum at 45 ℃ to constant weight to obtain PP-b-PMAA1.16g, wherein the yield is 80.2%.
Example 2
Preparation of a single-terminal hydroxy polyacryl chloride.
N2Under protection, adding single-terminal hydroxyl polypropylene (0.0984g,0.1mmol) and 50mL of toluene into a 100mL Schlenk bottle, stirring at 140 ℃ for 30min, adding succinyl chloride (4.65g,30mmol) after the polymer is completely dissolved, continuing to react at 140 ℃ for 10h, treating with anhydrous acetone after the reaction is finished, and drying to obtain 0.0972g of polypropylene product with an acyl chloride group at the terminal, wherein the yield is 85.3%.
Example 3
And (3) preparing the degradable polypropylene grafted sericin copolymer.
0.1g of sericin and 10mL of dioxane were added into a 50mL round bottom flask, the temperature was raised to 80 ℃ and after the single-terminal hydroxypolyacrylicide chloride was completely dissolved, the solution was gradually added dropwise to the single-terminal one prepared in example 2 and dissolved in 20mL of dioxaneHeating the hydroxyl polyacryl chloride product (4.5mmol,5.0g) to 105 ℃ for reacting for 8h, pouring the reaction liquid into absolute ethyl alcohol for precipitating, and filtering. Washing with anhydrous ethanol several times, washing with distilled water several times, and adding saturated Na2CO3Washing the solution, and finally washing the solution to be neutral by using water. Vacuum drying for 5h to obtain 0.83g of degradable polypropylene grafted sericin copolymer, wherein the yield is 75.4%.
Example 4
And (3) preparing the degradable polypropylene antibacterial material.
Taking 100 parts by weight of degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA), 100 parts by weight of degradable polypropylene grafted sericin copolymer, 20 parts by weight of nano calcium carbonate, 10 parts by weight of ethylene-1-octene copolymer and 1 part by weight of polyvinyl alcohol; weighing raw materials in a proportion of 0.5 part by weight of (2, 4-di-tert-butylphenyl) phosphite triester and 0.5 part by weight of 2-hydroxy-4-methoxydiphenylacetone, adding the raw materials into a high-speed mixer, setting the rotating speed of the high-speed mixer to 800 revolutions per minute, uniformly mixing the raw materials at normal temperature for 5min, putting the mixed raw materials into a parallel double-screw extruder, and performing melt extrusion and granulation, wherein the extrusion process comprises the following steps: the first zone is 160-170 ℃, the second zone is 170-180 ℃, the third zone is 180-190 ℃, the fourth zone is 170-180 ℃, the screw rotation speed is 300-350 r/min, the feeding frequency is 15-20 Hz, the melt pressure is 3.0-4.0 MPa, and the vacuum degree is-0.03-0.06 MPa, so that the degradable polypropylene antibacterial material is prepared.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (4)
1. A degradable polypropylene antibacterial material is characterized in that the degradable polypropylene antibacterial material is composed of degradable polypropylene, polymethacrylic acid block copolymer (PP-b-PMAA) and degradable polypropylene grafted sericin copolymer, the degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA) is 100 parts by weight, 100 parts of degradable polypropylene grafted sericin copolymer, 20 parts of nano calcium carbonate, 10 parts of ethylene-1-octene copolymer, 1 part of polyvinyl alcohol, 0.5 part of (2, 4-di-tert-butylphenyl) phosphite triester, 0.5 part of 2-hydroxy-4-methoxy-diphenylacetone, wherein the degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA) has a structure shown in a formula (I):
wherein n is 20-100, and m is 100-1000.
2. The method for preparing the degradable polypropylene antibacterial material according to claim 1, which is characterized by comprising the following steps:
the degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA) and the degradable polypropylene grafted sericin copolymer are prepared, wherein the degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA) accounts for 100 parts by weight, the degradable polypropylene grafted sericin copolymer accounts for 100 parts by weight, the nano calcium carbonate accounts for 20 parts by weight, the ethylene-1-octene copolymer accounts for 10 parts by weight, the polyvinyl alcohol accounts for 1 part by weight, the (2, 4-di-tert-butylphenyl) phosphite triester accounts for 0.5 part by weight, and the 2-hydroxy-4-methoxydiphenylacetone accounts for 0.5 part by weight in a high-speed mixer, and the mixed raw materials are placed in a parallel twin-screw extruder to be subjected to melt extrusion and granulation to prepare the degradable polypropylene antibacterial material.
3. The degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA) according to claim 2, wherein the preparation method of the degradable polypropylene and polymethacrylic acid block copolymer (PP-b-PMAA) comprises the following steps:
(1) carrying out amidation reaction on toluene serving as a solvent, pyridine serving as an acid-binding agent and RAFT reagent 4-cyano-4- (thiobenzoic acid) valeric acid, and then carrying out esterification reaction on the amidation reaction and single-end hydroxyl polypropylene to obtain a polypropylene macromolecule transfer agent, wherein the molar ratio of the 4-cyano-4- (thiobenzoic acid) valeric acid to the single-end hydroxyl polypropylene is 4: 1;
(2) and (2) taking N, N-dimethylformamide DMF as a solvent, azodiisobutyronitrile as an initiator, a polypropylene macromolecular chain transfer agent as a chain transfer agent and methacrylic acid as a monomer to obtain PP-b-PMAA, wherein the azodiisobutyronitrile and polypropylene macromolecular chain transfer agent are chain transfer agents, the molar ratio of the methacrylic acid to the azodiisobutyronitrile is 1:3:800, and the molar concentration of the methacrylic acid is 2 mol/L.
4. The degradable polypropylene graft sericin copolymer according to claim 2, wherein the preparation method of the degradable polypropylene graft sericin copolymer comprises the steps of:
(1)N2under protection, toluene is used as a solvent, and single-terminal hydroxyl polypropylene and succinyl chloride are used as raw materials to perform acyl chlorination reaction to obtain a polypropylene product with an acyl chloride group at the terminal, wherein the molar ratio of the single-terminal hydroxyl polypropylene to the succinyl chloride is 1: 300;
(2) the degradable polypropylene grafted sericin copolymer is prepared by using dioxane as a solvent and a single-terminal hydroxyl polyacryl chlorination product and sericin as raw materials, wherein the mass ratio of the single-terminal hydroxyl polyacryl chlorination product to the sericin is 1: 50.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112126092A (en) * | 2020-09-16 | 2020-12-25 | 彭军文 | Super-hydrophobic antibacterial polypropylene film and preparation method thereof |
| CN112142931A (en) * | 2020-09-16 | 2020-12-29 | 邓天生 | Ammonium salt antibacterial polyethylene material and preparation method thereof |
| CN112159508A (en) * | 2020-09-16 | 2021-01-01 | 邓天生 | Antibacterial polyethylene block copolymer and preparation method thereof |
| CN112831055A (en) * | 2021-01-13 | 2021-05-25 | 邱元栏 | Degradable flame-retardant polystyrene block copolymer and preparation method thereof |
| CN114892345A (en) * | 2022-05-09 | 2022-08-12 | 西南大学 | Antibacterial polypropylene non-woven fabric and preparation method and application thereof |
-
2020
- 2020-06-17 CN CN202010555582.5A patent/CN111621117A/en not_active Withdrawn
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112126092A (en) * | 2020-09-16 | 2020-12-25 | 彭军文 | Super-hydrophobic antibacterial polypropylene film and preparation method thereof |
| CN112142931A (en) * | 2020-09-16 | 2020-12-29 | 邓天生 | Ammonium salt antibacterial polyethylene material and preparation method thereof |
| CN112159508A (en) * | 2020-09-16 | 2021-01-01 | 邓天生 | Antibacterial polyethylene block copolymer and preparation method thereof |
| CN112831055A (en) * | 2021-01-13 | 2021-05-25 | 邱元栏 | Degradable flame-retardant polystyrene block copolymer and preparation method thereof |
| CN114892345A (en) * | 2022-05-09 | 2022-08-12 | 西南大学 | Antibacterial polypropylene non-woven fabric and preparation method and application thereof |
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Application publication date: 20200904 |