CN113429765B - Degradable PLA/PIM-1 air-conditioning film and preparation method and application thereof - Google Patents
Degradable PLA/PIM-1 air-conditioning film and preparation method and application thereof Download PDFInfo
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- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
- A23B7/144—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of gases, e.g. fumigation; Compositions or apparatus therefor
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
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- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
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- C08J2471/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
- C08J2471/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W90/00—Enabling technologies or technologies with a potential or indirect contribution to greenhouse gas [GHG] emissions mitigation
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Abstract
The invention discloses a degradable PLA/PIM-1 air-conditioning film and a preparation method and application thereof. The preparation method comprises the steps of reacting 5,5 ', 6,6 ' -tetrahydroxy-3, 3,3 ', 3 ' -tetramethyl-1, 1 ' -helical bis-indane with 2,3,5, 6-tetrafluoroterephthalonitrile to prepare PIM-1, and dissolving polylactic acid and PIM-1 in a solvent to prepare the PLA/PIM-1 modified atmosphere film. The degradable PLA/PIM-1 modified atmosphere film prepared by the invention is mainly prepared from polylactic acid, has high safety and is biodegradable, and the pollution to the environment is reduced to a certain extent. The obtained PLA/PIM-1 gas-regulating film has low cost and gas-regulating performance, and can be used in various fields of storage, transportation, fresh-keeping and the like of fruits and vegetables after being picked.
Description
Technical Field
The invention belongs to the technical field of biodegradable films and gas regulating films, and particularly relates to a degradable PLA/PIM-1 gas regulating film as well as a preparation method and application thereof.
Background
At present, the types of packaging films for fruit and vegetable products are various, such as Polyethylene (PE), polypropylene (PP), polyvinyl chloride (PVC), and the like. However, these packaging films are not easily degraded in nature rapidly by the action of various environmental factors, so that serious environmental hazards, so-called white pollution, of waste plastics occur, and the environment is seriously polluted. Meanwhile, the packaging films lack gas regulation performance, are not beneficial to storage and preservation of fruits and vegetables, and limit the application and development of the packaging films in the field of fruit and vegetable preservation. Therefore, the development of the packaging film which has the air-conditioning fresh-keeping function and can be naturally degraded is urgent.
With the rapid development of science and technology, the biodegradable material can be degraded into carbon dioxide, water, other biomasses and inorganic substances in a short time by the erosion of microorganisms, and is an environment low-load material. Polylactic acid, PLA for short, is a bio-based and renewable biodegradable material, and can be completely degraded by microorganisms in nature under specific conditions after being used, and finally carbon dioxide and water are generated, so that the polylactic acid has no pollution to the environment and has sustainable development. Meanwhile, the raw material required by the preparation of the polylactic acid is lactic acid, the lactic acid has wide sources and is mainly obtained by fermenting substances containing starch and cellulose, such as corn, sugarcane, beet, straw and the like, so that the preparation of the polylactic acid is simple and the yield is huge. Polylactic acid is an environment-friendly material, and can fundamentally solve the ecological problem caused by plastic pollution in the long run.
Currently, many researches are made on degradable materials. For example, patent CN202011587595.7 discloses a film material prepared by using polyethylene base material and aliphatic polyester degradation material as main raw materials through operations of extrusion, film blowing, tape casting, etc.; patent CN201911416093.5 discloses a preparation method of a degradable polylactic acid-glycolic acid material, which controls the degradation speed of the membrane material through a photocatalyst, and has a significant degradation effect in seawater. All the above patents regulate the degradation of degradation materialsThe invention in speed is less in research on the membrane gas-regulating performance of the degradable material serving as the main raw material. Patent CN202011098846.5 discloses a degradable modified atmosphere agricultural product packaging bag, which takes polyvinyl alcohol, silicon dioxide, glycerol and calcium carbonate as raw materials to prepare O 2 /CO 2 Has excellent permeability and moisture permeability, and can be degraded in the open air. The preparation method of the modified atmosphere packaging film taking polylactic acid as a raw material is still rare. Therefore, the research on the preparation method of the degradable modified atmosphere packaging film taking the polylactic acid as the raw material has wide application prospect and market.
Disclosure of Invention
In order to overcome the defects and shortcomings in the prior art, the invention aims to provide a preparation method of a degradable PLA/PIM-1 modified atmosphere film. The film is prepared by taking PLA as a main raw material, has excellent degradability and good air-conditioning property, and can be applied to the air-conditioning preservation of fruits and vegetables.
The invention also aims to provide a degradable PLA/PIM-1 modified atmosphere film prepared by the method.
The invention further aims to provide application of the degradable PLA/PIM-1 modified atmosphere film.
The purpose of the invention is realized by the following technical scheme:
a preparation method of a degradable PLA/PIM-1 modified atmosphere film comprises the following steps:
(1) uniformly mixing 5,5 ', 6,6 ' -tetrahydroxy-3, 3,3 ', 3 ' -tetramethyl-1, 1 ' -spiral bis-indane (TTSBI), 2,3,5, 6-tetrafluoroterephthalonitrile (TFTPN), a catalyst and a solvent, reacting under the protection of inert gas or nitrogen, filtering, washing and drying to obtain PIM-1;
(2) and (2) dissolving polylactic acid (PLA) and PIM-1 in a solvent, uniformly mixing to obtain a homogeneous membrane casting solution, and preparing a degradable PLA/PIM-1 modified atmosphere membrane.
Preferably, the molar ratio of the 5,5 ', 6,6 ' -tetrahydroxy-3, 3,3 ', 3 ' -tetramethyl-1, 1 ' -spirobiindane (TTSBI), 2,3,5, 6-tetrafluoroterephthalonitrile (TFTPN) and the catalyst in step (1) is (1-2): (1-2): (2-4); more preferably 1:1: 2.
Preferably, the catalyst in the step (1) is anhydrous K 2 CO 3 。
Preferably, the ratio of the 5,5 ', 6,6 ' -tetrahydroxy-3, 3,3 ', 3 ' -tetramethyl-1, 1 ' -spirobiindane to the solvent in step (1) is (1-2) g: (40-200) mL.
Preferably, the solvent in step (1) is N-N-Dimethylformamide (DMF).
Preferably, the reaction in the step (1) is carried out at a suitable temperature of 50-80 ℃ for 12-48 h.
Preferably, the 5,5 ', 6,6 ' -tetrahydroxy-3, 3,3 ', 3 ' -tetramethyl-1, 1 ' -spirobiindane (TTSBI) in step (1) is recrystallized and dried before use, and the 2,3,5, 6-tetrafluoroterephthalonitrile (TFTPN) is purified by sublimation before use.
Preferably, the specific steps of suction filtration, washing and drying in the step (1) are as follows: after the reaction is finished, adding an HCl solution with the concentration of 0.1-0.5 wt% into the product mixed solution, stirring to remove redundant catalyst, then respectively washing the product with methanol and deionized water until the washing liquid is neutral, performing suction filtration to obtain a product, and finally performing vacuum drying at 80-140 ℃ for more than 24 hours to obtain PIM-1 powder.
More preferably, the volume ratio of the product mixed solution to the HCl solution is (40-200): (3-5).
Preferably, the mass ratio of the polylactic acid (PLA) to the PIM-1 in the step (2) is (4-20): (0.1-2).
Preferably, in the homogeneous membrane casting solution in the step (2), the mass of the polylactic acid is 4-20%.
Preferably, the solvent in step (2) is dichloromethane.
Preferably, the film preparation method in the step (2) is a flat film preparation method, and the film is dried to form a film, wherein the temperature for drying the film is 30-50 ℃, and the drying time is 10-60 min.
Preferably, the thickness of the degradable PLA/PIM-1 modified atmosphere film in the step (2) is 30-80 μm.
The degradable PLA/PIM-1 modified atmosphere film prepared by the method.
The degradable PLA/PIM-1 air-conditioning film is applied to the field of storage and preservation of fruits and vegetables.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the membrane material prepared by the invention is mainly prepared from polylactic acid, has degradability, wide source and lower cost.
(2) The invention adds PIM-1 into PLA to obtain PLA/PIM-1 composite membrane, so that the membrane material has air-conditioning performance.
(3) The degradable PLA/PIM-1 air-conditioning membrane prepared by the invention has simple process and is suitable for large-scale industrial production.
(4) The PLA/PIM-1 air-conditioned film prepared by the invention can delay decay and deterioration of picked fruits and vegetables and prolong the storage time.
(5) The PLA/PIM-1 air-conditioned membrane prepared by the invention can be applied to various links of storage, transportation, sale and the like of the picked fruits and vegetables, and has wide application prospect.
Drawings
FIG. 1 is a photograph of a sample of the PLA/PIM-1 composite film obtained in examples 1 to 4.
FIG. 2 shows the moisture permeability test results of the PLA/PIM-1 composite membranes obtained in examples 1 to 4. .
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the embodiments of the present invention are not limited thereto.
Those who do not specify specific conditions in the examples of the present invention follow conventional conditions or conditions recommended by the manufacturer. The raw materials, reagents and the like which are not indicated for manufacturers are all conventional products which can be obtained by commercial purchase.
Example 1
(1) 40mL of DMF solution was added to a three-necked flask, and 1.204g of TFTPN, 2.05g of TTSBI, and 1.664g K were weighed out 2 CO 3 Adding into a three-neck flask. Nitrogen was added and the reaction was stirred magnetically at 60 ℃ for 24 h.
(2) 3mL of 0.1 wt% HCl solution was added to the product of step (1) and stirred for 30min to remove excess K 2 CO 3 And then respectivelyAnd (4) washing the product with methanol and deionized water until the washing liquid is neutral, and performing suction filtration to obtain the product. The final product was dried under vacuum at 120 ℃ for 24h to obtain PIM-1 powder.
(3) 7g of PLA and 0.25g of PIM-1 were weighed out and dissolved in methylene chloride, and the whole reaction system was 100 mL. And uniformly stirring at room temperature to obtain a homogeneous membrane casting solution. And (3) inverting the casting solution on a clean glass plate, adjusting a film scraping knife to 50 mu m thickness, preparing a film by using a flat film forming method, and drying at 30 ℃ for 15min to obtain the PLA/PIM-1 composite film.
Example 2
(1) 80mL of DMF solution was added to a three-necked flask, and 2.408g of TFTPN, 2.05g of TTSBI, and 3.328g K g of TTSBI were weighed out separately 2 CO 3 Adding into a three-neck flask. Nitrogen is added, and the reaction is carried out for 24 hours under the condition of magnetic stirring at 60 ℃.
(2) 5mL of 0.1 wt% HCl solution was added to the product of step (1), and stirred for 30min to remove excess K 2 CO 3 And cleaning the product with methanol and deionized water, and filtering until the cleaning solution is neutral. The final product was dried under vacuum at 120 ℃ for 24h to obtain PIM-1 powder.
(3) 7g of PLA and 0.5g of PIM-1 were weighed out and dissolved in methylene chloride, and the whole reaction system was 100 mL. And uniformly stirring at room temperature to obtain a homogeneous membrane casting solution. And (3) inverting the casting solution on a clean glass plate, adjusting a film scraping knife to be 100 microns thick, scraping the film by using a flat film forming method, and drying for 30min at 30 ℃ to obtain the PLA/PIM-1 composite film.
Example 3
(1) 80mL of DMF solution was added to a three-necked flask, and 2.408g of TFTPN, 4.10g of TTSBI, and 4.992g K g of TTSBI were weighed out separately 2 CO 3 Adding into a three-neck flask. Nitrogen is added, and the reaction is carried out for 24 hours under the condition of magnetic stirring at 60 ℃.
(2) 5mL of 0.1 wt% HCl solution was added to the product of step (1), and stirred for 30min to remove excess K 2 CO 3 And cleaning the product with methanol and deionized water, and filtering until the cleaning solution is neutral. The final product was dried under vacuum at 120 ℃ for 24h to obtain PIM-1 powder.
(3) 7g of PLA and 0.25g of PIM-1 were weighed out and dissolved in methylene chloride, and the whole reaction system was 100 mL. And uniformly stirring at room temperature to obtain a homogeneous membrane casting solution. And (3) inverting the casting solution on a clean glass plate, adjusting a film scraping knife to the thickness of 100 mu m, scraping the film by using a flat film forming method, and drying for 10min at 40 ℃ to obtain the PLA/PIM-1 composite film.
Example 4
(1) 40mL of DMF solution was added to a three-necked flask, and 1.204g of TTSBI, 4.10g of TFTPN, and 3.328g K were weighed out respectively 2 CO 3 Adding into a three-neck flask. Nitrogen is added, and the reaction is carried out for 24 hours under the condition of magnetic stirring at 60 ℃.
(2) 3mL of 0.1 wt% HCl solution was added to the product of step (1) and stirred for 30min to remove excess K 2 CO 3 And cleaning the product with methanol and deionized water, and filtering until the cleaning solution is neutral. The final product was dried under vacuum at 120 ℃ for 24h to obtain PIM-1 powder.
(3) 7g of PLA and 0.25g of PIM-1 were weighed out and dissolved in methylene chloride, and the whole reaction system was 100 mL. And uniformly stirring at room temperature to obtain a homogeneous membrane casting solution. And (3) inverting the casting solution on a clean glass plate, adjusting a film scraping knife to be 100 microns thick, scraping the film by using a flat film forming method, and drying for 20min at 30 ℃ to obtain the PLA/PIM-1 composite film.
As shown in figure 1, the PLA/PIM-1 composite membrane after the PIM-1 is added is fluorescent yellow in color and has good transparency. In addition, compared with the PLA film sold in the market, the PLA/PIM-1 composite film of 4 embodiments has certain improvement in air permeability, and can convey certain O for the storage and transportation of fruits and vegetables after the fruits and vegetables are harvested 2 So that the fruits and vegetables maintain a low oxygen consumption dormant state, thereby prolonging the preservation time. Meanwhile, the PLA/PIM-1 composite film has higher moisture permeability than a PLA film, and can output water molecules in a storage environment in time, so that the storage environment is kept relatively dry, and the growth of microorganisms is inhibited.
TABLE 1 results of air permeability test of PLA/PIM-1 composite films obtained in examples 1 to 4
Note: the PLA film in table 1 and fig. 2 was manufactured by cantonese macro packaging materials ltd (china guangdong) and purchased from a local supermarket.
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 (7)
1. The application of the degradable PLA/PIM-1 modified atmosphere film in the field of fruit and vegetable storage and preservation is characterized in that the degradable PLA/PIM-1 modified atmosphere film is prepared by the following steps:
(1) uniformly mixing 5,5 ', 6,6 ' -tetrahydroxy-3, 3,3 ', 3 ' -tetramethyl-1, 1 ' -spiral bisindane, 2,3,5, 6-tetrafluoroterephthalonitrile, a catalyst and a solvent, reacting for 12-48 h at 50-80 ℃ in an inert gas or nitrogen atmosphere, and performing suction filtration, washing and drying to obtain PIM-1;
(2) dissolving polylactic acid and PIM-1 in a solvent, uniformly mixing to obtain a homogeneous membrane casting solution, and preparing a degradable PLA/PIM-1 modified atmosphere membrane;
the mass ratio of the polylactic acid to the PIM-1 in the step (2) is (4-20): (0.1-2).
2. The application of the degradable PLA/PIM-1 modified atmosphere film in the field of fruit and vegetable storage and preservation according to claim 1, wherein the molar ratio of the 5,5 ', 6,6 ' -tetrahydroxy-3, 3,3 ', 3 ' -tetramethyl-1, 1 ' -spirobiindane, 2,3,5, 6-tetrafluoroterephthalonitrile and the catalyst in the step (1) is (1-2): (1-2): (2-4).
3. The application of the degradable PLA/PIM-1 modified atmosphere film in the field of fruit and vegetable storage and preservation according to claim 1, wherein the catalyst in the step (1) is anhydrous K 2 CO 3 。
4. The application of the degradable PLA/PIM-1 modified atmosphere film in the field of fruit and vegetable storage and preservation according to claim 1, wherein the film-forming method in the step (2) is a flat film-forming method, and the film is dried to form a film, wherein the temperature of the dried film is 30-50 ℃, and the drying time is 10-60 min.
5. The application of the degradable PLA/PIM-1 modified atmosphere film in the field of fruit and vegetable storage and preservation according to claim 1, wherein in the homogeneous film casting solution in the step (2), the mass of polylactic acid accounts for 4-20%;
the ratio of the 5,5 ', 6,6 ' -tetrahydroxy-3, 3,3 ', 3 ' -tetramethyl-1, 1 ' -helical biindane to the solvent in the step (1) is (1-2) g: (40-200) mL.
6. The application of the degradable PLA/PIM-1 modified atmosphere film in the field of fruit and vegetable storage and preservation according to claim 1, wherein the solvent in the step (1) is N-N-dimethylformamide;
the specific steps of suction filtration, washing and drying in the step (1) are as follows: after the reaction is finished, adding an HCl solution with the concentration of 0.1-0.5 wt% into the product mixed solution, stirring to remove redundant catalyst, then respectively washing the product with methanol and deionized water until the washing liquid is neutral, performing suction filtration, and finally performing vacuum drying at 80-140 ℃ for 24 hours to obtain PIM-1 powder;
the volume ratio of the product mixed solution to the HCl solution is (40-200): (3-5);
the solvent in the step (2) is dichloromethane.
7. The application of the degradable PLA/PIM-1 modified atmosphere film in the field of fruit and vegetable storage and preservation according to claim 1, wherein the thickness of the degradable PLA/PIM-1 modified atmosphere film is 30-80 μm.
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Non-Patent Citations (4)
| Title |
|---|
| "Solution-Processed, Organophilic Membrane Derived from a Polymer of Intrinsic Microporosity";Peter M. Budd. et al;《ADVANCED MMATERIALS》;20040308;第16卷(第5期);第456-459页 * |
| "Towards enhanced CO2 selectivity of the PIM-1 membrane by blending with polyethylene glycol";Xin Mei Wu et al;《Journal of Membrane Science》;20150623;第493卷;第147-155页 * |
| "Tunable Porosity in Fused Filament 3D-Printed Blends of Intrinsically Porous Polymer and Thermoplastic Aliphatic Polyesters Polycaprolactone and Polylactic Acid";Zachary C. Kennedy et al;《ACS Applied Polymer Materials》;20190207;第1卷(第3期);第482-492页 * |
| Zachary C. Kennedy et al."Tunable Porosity in Fused Filament 3D-Printed Blends of Intrinsically Porous Polymer and Thermoplastic Aliphatic Polyesters Polycaprolactone and Polylactic Acid".《ACS Applied Polymer Materials》.2019,第1卷(第3期),第482-492页. * |
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