CN115160612A - Synthesis process and application of polyethylene mildew-proof preservative film - Google Patents
Synthesis process and application of polyethylene mildew-proof preservative film Download PDFInfo
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- CN115160612A CN115160612A CN202210914331.0A CN202210914331A CN115160612A CN 115160612 A CN115160612 A CN 115160612A CN 202210914331 A CN202210914331 A CN 202210914331A CN 115160612 A CN115160612 A CN 115160612A
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Abstract
The invention relates to the technical field of polyethylene films and discloses a synthesis process and application of a polyethylene mildew-proof preservative film.
Description
Technical Field
The invention relates to the technical field of polyethylene films, in particular to a polyethylene mildew-proof preservative film.
Background
The polyethylene preservative film plays an important role in food transportation, preservation and the like, and the polyethylene is blended and modified by using hyperbranched polymers, inorganic nano particles and the like, so that the antibacterial property of the polyethylene preservative film can be improved, the performances such as air permeability, water permeability, mechanical strength and the like can be improved, the practical application of the polyethylene in materials such as preservative films is expanded, and the likePreparation of alkene mildew-proof preservative film 2 The particles are subjected to surface modification, and then are used as an antibacterial agent and then are blended with polyethylene for blow molding to form a film, and the obtained preservative film has excellent mechanical properties and antibacterial and mildewproof effects.
The invention aims to modify the surface of the nano zinc oxide, improve the interface bonding and the dispersibility with polyethylene groups, improve the mechanical property and the antibacterial property of polyethylene film materials, and expand the development and the application of polyethylene in materials such as preservative films.
Disclosure of Invention
Technical problem to be solved
Aiming at the defects of the prior art, the invention provides a polyethylene mildew-proof preservative film with excellent antibacterial property.
(II) technical scheme
In order to achieve the purpose, the invention provides the following technical scheme: the polyethylene mildew-proof preservative film comprises the following synthetic processes:
s1, adding 4- (tert-butyloxycarbonylamino) benzoic acid into thionyl chloride, and reacting the obtained product with N 2 Heating to 55-70 ℃ in the atmosphere to react for 4-8 h, performing rotary evaporation to remove thionyl chloride after the reaction, dissolving 360-450 parts by weight of acyl chloride product into a reaction solvent, adding 100 parts by weight of 2,2-dimethylolpropionic acid and 150-220 parts by weight of triethylamine, stirring to react for 6-18 h at 0-25 ℃, performing rotary evaporation to remove the solvent after the reaction, adding the product into ethyl acetate to perform recrystallization to obtain bis [4- (tert-butoxycarbonylamino) benzoate]Propionic acid.
S2, adding 100 parts by weight of bis [4- (tert-butoxycarbonylamino) benzoate ] propionic acid and 160-250 parts by weight of trifluoroacetic acid into dichloromethane, stirring and reacting at 15-35 ℃ for 2-5 h, removing the solvent by rotary evaporation after reaction, washing with deionized water, adding the product into ethyl acetate, and recrystallizing to obtain bis [ 4-aminobenzoate ] propionic acid.
S3, adding bis [ 4-aminobenzoate ] propionic acid into N-methylpyrrolidone and toluene as a water-carrying agent, stirring at 150-165 ℃ to react for 10-20 h, cooling after the reaction, adding deionized water to precipitate, filtering the solvent, and washing the product with the deionized water and ethanol to obtain the hyperbranched polyesteramide.
S4, adding 100 parts by weight of nano zinc oxide and 50-150 parts by weight of toluene 2,4-diisocyanate into a toluene solvent, uniformly dispersing, adding 0.5-1.2 parts by weight of dibutyltin dilaurate, reacting at 50-65 ℃ for 3-8 h, after reaction, centrifugally separating, dispersing the product into the reaction solvent, adding 100-300 parts by weight of hyperbranched polyesteramide, reacting at 70-90 ℃ for 6-12 h, after reaction, centrifugally separating, washing the product with deionized water and ethanol, and obtaining the hyperbranched polyesteramide modified zinc oxide.
S5, adding the low-density polyethylene, the hyperbranched polyesteramide modified zinc oxide and 0.1-0.4% of dispersing agent into a double-screw extruder for blending and extruding, and then casting a film through a co-extrusion casting machine to obtain the polyethylene mildew-proof preservative film.
Preferably, the reaction solvent in S1 includes toluene, ethyl acetate, dichloromethane, chloroform, and tetrahydrofuran.
Preferably, the volume ratio of the N-methyl pyrrolidone to the toluene in the S3 is 1.
Preferably, the reaction solvent in S3 includes N-methylpyrrolidone, N-dimethylformamide, and N, N-dimethylacetamide.
Preferably, the amount of the hyperbranched polyesteramide modified zinc oxide in the S5 is 0.2-2% of that of the low-density polyethylene.
(III) advantageous technical effects
Compared with the prior art, the invention has the following beneficial technical effects:
the polyethylene mildew-proof preservative film takes bis [ 4-aminobenzoate ] propionic acid as a hyperbranched monomer, and synthesizes novel hyperbranched polyesteramide through amidation condensation high-temperature reaction; then, the surface of nano zinc oxide is modified by toluene 2,4-diisocyanate, and the introduced isocyanate group reacts with amino at the end position of hyperbranched polyesteramide, so that the hyperbranched polyesteramide is grafted to the surface of the nano zinc oxide, the surface modification of the nano zinc oxide is realized, the nano zinc oxide is used as an antibacterial modifier to be blended with low-density polyethylene to form a membrane, a polyethylene mildew-proof preservative membrane is obtained, the interface bonding strength and the dispersibility between the nano zinc oxide and a polyethylene matrix are improved after the nano zinc oxide is modified by the hyperbranched polyesteramide, a physical crosslinking site is formed in the polyethylene matrix, the mechanical strength of the polyethylene membrane is improved, the uniformly dispersed nano zinc oxide has better photocatalytic activity and antibacterial performance, the membrane material is endowed with excellent mildew-proof and antibacterial effects, and the development and application of polyethylene in the aspects of preservative membranes and the like are expanded.
Drawings
FIG. 1 is a scheme of a synthesis process of hyperbranched polyesteramide.
FIG. 2 is a tensile property test table of the polyethylene mildewproof preservative film.
Fig. 3 is a bacteriostatic activity test table of the polyethylene mildewproof preservative film.
Detailed Description
Example 1
S1, adding 0.5 g of 4- (tert-butoxycarbonylamino) benzoic acid to 5 mL of thionyl chloride, and adding the mixture to N 2 Heating to 55 ℃ in atmosphere, reacting 8 h, performing rotary evaporation to remove thionyl chloride after the reaction, dissolving an acyl chloride product of 0.36 g in an ethyl acetate reaction solvent, adding 2,2-dimethylolpropionic acid in parts by weight of 0.1 g and triethylamine in 0.15 g, stirring at 0 ℃ to react 18 h, performing rotary evaporation to remove the solvent after the reaction, adding the product into ethyl acetate, and performing recrystallization to obtain the bis [4- (tert-butoxycarbonylamino) benzoate]Propionic acid.
S2, adding 0.5 part by weight of g of bis [4- (tert-butoxycarbonylamino) benzoate ] propionic acid and 1.1 part by weight of g of trifluoroacetic acid into dichloromethane of 20 mL, stirring and reacting at 35 ℃ for 4 h, removing the solvent by rotary evaporation after reaction, washing with deionized water, adding the product into ethyl acetate, and recrystallizing to obtain bis [ 4-aminobenzoate ] propionic acid.
S3, adding 0.2 g bis [ 4-aminobenzoate ] propionic acid into N-methyl pyrrolidone with the volume ratio of 10 mL and water-carrying agent toluene with the volume ratio of 8 mL, stirring and reacting at 165 ℃ for 10 h, cooling after reaction, adding deionized water for precipitation, filtering a solvent, and washing a product by the deionized water and ethanol to obtain the hyperbranched polyesteramide.
S4, adding 1 g nano zinc oxide and 1 g toluene 2,4-diisocyanate into 100 mL toluene solvent, uniformly dispersing, adding 0.005 g dibutyltin dilaurate, reacting 4 h at 65 ℃, centrifugally separating after reaction, dispersing the product into N-methyl pyrrolidone reaction solvent, adding 2 g hyperbranched polyester amide, reacting 12 h at 70 ℃, centrifugally separating after reaction, washing the product with deionized water and ethanol, and obtaining the hyperbranched polyester amide modified zinc oxide.
S5, adding low-density polyethylene, 0.2% of hyperbranched polyesteramide modified zinc oxide and 0.3% of dispersant stearic acid into a double-screw extruder for blending and extruding, and then casting a film through a co-extrusion casting machine to obtain the polyethylene mildew-proof preservative film.
Example 2
S1, adding 0.5 g of 4- (tert-butoxycarbonylamino) benzoic acid to 5 mL of thionyl chloride, and adding the mixture to N 2 Heating to 60 ℃ in atmosphere, reacting for 6 h, removing thionyl chloride by rotary evaporation after the reaction, dissolving acyl chloride products of 0.36 g in a toluene reaction solvent, adding 2,2-dimethylolpropionic acid in parts by weight of 0.1 g and triethylamine of 0.2 g, stirring and reacting for 18 h at 0 ℃, removing the solvent by rotary evaporation after the reaction, adding the products into ethyl acetate, and recrystallizing to obtain bis [4- (tert-butoxycarbonylamino) benzoate]Propionic acid.
S2, adding 0.5 part by weight of g parts by weight of bis [4- (tert-butoxycarbonylamino) benzoate ] propionic acid and 0.8 part by weight of trifluoroacetic acid g into 30 mL dichloromethane, stirring and reacting at 35 ℃ for 4 h, removing the solvent by rotary evaporation after reaction, washing with deionized water, adding the product into ethyl acetate, and recrystallizing to obtain bis [ 4-aminobenzoate ] propionic acid.
S3, adding 0.2 g bis [ 4-aminobenzoate ] propionic acid into N-methyl pyrrolidone with the volume ratio of 10 mL and 6 mL water-carrying agent toluene, stirring and reacting at 165 ℃ for 10 h, cooling after reaction, adding deionized water for precipitation, filtering a solvent, and washing a product by the deionized water and ethanol to obtain the hyperbranched polyesteramide.
S4, adding 1 g nano zinc oxide and 0.8 g toluene 2,4-diisocyanate into 50 mL toluene solvent, uniformly dispersing, adding 0.005 g dibutyltin dilaurate, reacting at 65 ℃ for 3 h, after reaction, centrifugally separating, dispersing the product into N, N-dimethylacetamide reaction solvent, adding 2.5 g hyperbranched polyester amide, reacting at 90 ℃ for 6 h, after reaction, centrifugally separating, washing the product with deionized water and ethanol, and obtaining the hyperbranched polyester amide modified zinc oxide.
S5, adding low-density polyethylene, 0.8% of hyperbranched polyesteramide modified zinc oxide and 0.3% of dispersant stearic acid into a double-screw extruder for blending and extruding, and then casting a film through a co-extrusion casting machine to obtain the polyethylene mildew-proof preservative film.
Example 3
S1, adding 0.5 g of 4- (tert-butoxycarbonylamino) benzoic acid to 10 mL of thionyl chloride, and adding the mixture to N 2 Heating to 70 ℃ in atmosphere to react 6 h, performing rotary evaporation to remove thionyl chloride after the reaction, dissolving an acyl chlorination product of 0.42 g in a trichloromethane reaction solvent, adding 2,2-dimethylolpropionic acid in parts by weight of 0.1 g and triethylamine in 0.22 g, stirring to react at 10 ℃ for 12 h, performing rotary evaporation to remove the solvent after the reaction, adding the product into ethyl acetate to perform recrystallization to obtain the bis [4- (tert-butoxycarbonylamino) benzoate]Propionic acid.
S2, adding 0.5 part by weight of g parts by weight of bis [4- (tert-butoxycarbonylamino) benzoate ] propionic acid and 0.8 part by weight of trifluoroacetic acid g into dichloromethane of 30 mL, stirring and reacting at 35 ℃ for 2 h, removing the solvent by rotary evaporation after reaction, washing with deionized water, adding the product into ethyl acetate, and recrystallizing to obtain bis [ 4-aminobenzoate ] propionic acid.
S3, adding 0.2 g bis [ 4-aminobenzoate ] propionic acid into N-methyl pyrrolidone with the volume ratio of 10 mL and 8 mL water-carrying agent toluene, stirring and reacting at 165 ℃ for 12 h, cooling after reaction, adding deionized water for precipitation, filtering a solvent, and washing a product by the deionized water and ethanol to obtain the hyperbranched polyesteramide.
S4, adding 1 g nano zinc oxide and 1.5 g toluene 2,4-diisocyanate into 100 mL toluene solvent, uniformly dispersing, adding 0.012 g dibutyltin dilaurate, reacting at 50 ℃ for 5 h, after reaction, centrifugally separating, dispersing the product into N, N-dimethylformamide reaction solvent, adding 1 g hyperbranched polyester amide, reacting at 80 ℃ for 12 h, after reaction, centrifugally separating, washing the product with deionized water and ethanol, and obtaining the hyperbranched polyester amide modified zinc oxide.
S5, adding low-density polyethylene, 1.5% of hyperbranched polyesteramide modified zinc oxide and 0.2% of dispersant stearic acid into a double-screw extruder for blending and extruding, and then casting a film through a co-extrusion casting machine to obtain the polyethylene mildew-proof preservative film.
Example 4
S1, adding 0.5 g 4- (tert-butoxycarbonylamino) benzoic acid to 5 mL thionyl chloride, in N 2 Heating to 70 ℃ in atmosphere to react 6 h, performing rotary evaporation to remove thionyl chloride after the reaction, dissolving an acyl chlorination product of 0.42 g in a trichloromethane reaction solvent, adding 2,2-dimethylolpropionic acid in parts by weight of 0.1 g and triethylamine in 0.2 g, stirring to react at 0 ℃ for 18 h, performing rotary evaporation to remove the solvent after the reaction, adding the product into ethyl acetate to perform recrystallization to obtain the bis [4- (tert-butoxycarbonylamino) benzoate]Propionic acid.
S2, adding 0.5 part by weight of g parts by weight of bis [4- (tert-butoxycarbonylamino) benzoate ] propionic acid and 1 g trifluoroacetic acid into 20 mL dichloromethane, stirring and reacting at 35 ℃ for 4 h, removing the solvent by rotary evaporation after reaction, washing with deionized water, adding the product into ethyl acetate, and recrystallizing to obtain bis [ 4-aminobenzoate ] propionic acid.
S3, adding 0.2 g bis [ 4-aminobenzoate ] propionic acid into N-methyl pyrrolidone with the volume ratio of 10 mL and toluene with the volume ratio of 5 mL, stirring and reacting at 165 ℃ for 18 h, cooling after reaction, adding deionized water for precipitation, filtering a solvent, and washing a product by the deionized water and ethanol to obtain the hyperbranched polyesteramide.
S4, adding 1 g nano zinc oxide and 1.2 g toluene 2,4-diisocyanate into 100 mL toluene solvent, uniformly dispersing, adding 0.01 g dibutyltin dilaurate, reacting at 65 ℃ for 8 h, after reaction, centrifugally separating, then dispersing the product into N-methyl pyrrolidone reaction solvent, adding 1 g hyperbranched polyesteramide, reacting at 70 ℃ for 10 h, after reaction, centrifugally separating, washing the product with deionized water and ethanol, and obtaining the hyperbranched polyesteramide modified zinc oxide.
S5, adding low-density polyethylene, 2% of hyperbranched polyesteramide modified zinc oxide and 0.3% of dispersant stearic acid into a double-screw extruder for blending and extruding, and then casting a film through a co-extrusion casting machine to obtain the polyethylene mildew-proof preservative film.
The tensile strength of the polyethylene mildewproof preservative film is tested by a universal material testing machine, the tensile rate is 10 mm/min, and the film sample is 120 mm multiplied by 60 mm multiplied by 4mm.
Remove 10 of 0.1 mL 4 The bacterial suspension of the CFU/mL staphylococcus aureus is dripped into an agar culture medium, the polyethylene mildew-proof preservative film (a circular sample with the radius of 0.5 cm) prepared in the embodiment is added to serve as an experimental group, the preservative film is not added to serve as a blank group, the polyethylene mildew-proof preservative film is cultured in a constant-temperature incubator under the illumination of 24 h respectively, the total number of the viable bacteria is measured through a flat plate technology method, and the bacteriostasis rate is calculated.
Claims (5)
1. A synthetic process of a polyethylene mildew-proof preservative film comprises low-density polyethylene and a dispersing agent, and is characterized in that: the synthesis process comprises the following steps:
s1, adding 4- (tert-butyloxycarbonylamino) benzoic acid into thionyl chloride, and reacting the obtained product with N 2 Heating to 55-70 ℃ in atmosphere to react for 4-8 h, dissolving 360-450 parts by weight of acyl chloride product in a reaction solvent, adding 100 parts by weight of 2,2-dimethylolpropionic acid and 150-220 parts by weight of triethylamine, and stirring at 0-25 ℃ to react for 6-18 h to obtain bis [4- (tert-butoxycarbonylamino) benzoate]Propionic acid;
s2, adding 100 parts by weight of bis [4- (tert-butoxycarbonylamino) benzoate ] propionic acid and 160-250 parts by weight of trifluoroacetic acid into dichloromethane, and stirring and reacting at 15-35 ℃ for 2-5 h to obtain bis [ 4-aminobenzoate ] propionic acid;
s3, adding di [ 4-aminobenzoate ] propionic acid into N-methylpyrrolidone and toluene as a water-carrying agent, and stirring at 150-165 ℃ to react for 10-20 h to obtain hyperbranched polyesteramide;
s4, adding 100 parts by weight of nano zinc oxide and 50-150 parts by weight of toluene 2,4-diisocyanate into a toluene solvent, uniformly dispersing, adding 0.5-1.2 parts by weight of dibutyltin dilaurate, reacting at 50-65 ℃ for 3-8 h, after reaction, centrifugally separating, dispersing a product into a reaction solvent, adding 100-300 parts by weight of hyperbranched polyesteramide, and reacting at 70-90 ℃ for 6-12 h to obtain hyperbranched polyesteramide modified zinc oxide;
s5, adding the low-density polyethylene, the hyperbranched polyesteramide modified zinc oxide and 0.1-0.4% of dispersing agent into a double-screw extruder for blending and extruding, and then casting a film by a co-extrusion casting machine to obtain the polyethylene mildew-proof preservative film.
2. The synthesis process of the polyethylene mildewproof preservative film according to the claim 1, which is characterized in that: the reaction solvent in S1 comprises toluene, ethyl acetate, dichloromethane, trichloromethane and tetrahydrofuran.
3. The synthesis process of the polyethylene mildewproof preservative film according to the claim 1, which is characterized in that: the volume ratio of the N-methyl pyrrolidone to the toluene in the S3 is 1.4-0.8.
4. The synthesis process of the polyethylene mildewproof preservative film according to the claim 1, which is characterized in that: the reaction solvent in S3 comprises N-methyl pyrrolidone, N-dimethylformamide and N, N-dimethylacetamide.
5. The synthesis process of the polyethylene mildewproof preservative film according to the claim 1, characterized in that: the dosage of the hyperbranched polyesteramide modified zinc oxide in the S5 is 0.2-2% of that of the low-density polyethylene.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116082732A (en) * | 2022-12-26 | 2023-05-09 | 中天科盛科技股份有限公司 | Antibacterial polyethylene food-grade packaging film and preparation method thereof |
| CN118085444A (en) * | 2024-04-29 | 2024-05-28 | 杭州星点包装材料有限公司 | Antibacterial sealing film and preparation method thereof |
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2022
- 2022-08-01 CN CN202210914331.0A patent/CN115160612A/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116082732A (en) * | 2022-12-26 | 2023-05-09 | 中天科盛科技股份有限公司 | Antibacterial polyethylene food-grade packaging film and preparation method thereof |
| CN118085444A (en) * | 2024-04-29 | 2024-05-28 | 杭州星点包装材料有限公司 | Antibacterial sealing film and preparation method thereof |
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