CN114369340B - Material containing ultraviolet absorbent and preparation method thereof - Google Patents
Material containing ultraviolet absorbent and preparation method thereof Download PDFInfo
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- CN114369340B CN114369340B CN202111394491.9A CN202111394491A CN114369340B CN 114369340 B CN114369340 B CN 114369340B CN 202111394491 A CN202111394491 A CN 202111394491A CN 114369340 B CN114369340 B CN 114369340B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- 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
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G13/00—Protecting plants
- A01G13/02—Protective coverings for plants; Coverings for the ground; Devices for laying-out or removing coverings
- A01G13/0256—Ground coverings
- A01G13/0268—Mats or sheets, e.g. nets or fabrics
- A01G13/0275—Films
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
- C08J3/226—Compounding polymers with additives, e.g. colouring using masterbatch techniques using a polymer as a carrier
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
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- C—CHEMISTRY; METALLURGY
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
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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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture
- Y02A40/28—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture specially adapted for farming
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Abstract
The invention relates to a material containing an ultraviolet absorber, a preparation method and application thereof. The general molecular formula of the structure of the ultraviolet absorber isWherein the method comprises the steps of
Description
Technical Field
The invention relates to an anti-ultraviolet aging biodegradable material, such as master batch or film, which can effectively absorb multiband ultraviolet light.
Background
Ultraviolet absorbers are a class of substances that can absorb ultraviolet light in sunlight or fluorescent light sources, convert it into harmless energy and release it without itself being altered. A large amount of harmful ultraviolet light (the wavelength is mainly concentrated at 280-400 nm) contained in sunlight irradiates the surface of the biodegradable mulch film material to cause the performance degradation and the function degradation of the material, and the damage of ultraviolet light to the biodegradable mulch film material can be relieved to a certain extent by using an ultraviolet absorbent.
The ultraviolet aging resistant biodegradable mulching film is a functional agricultural film which can reduce the damage of ultraviolet light to a ground film material by introducing an ultraviolet absorbent so as to prolong the service life of the mulching film. The ultraviolet absorber in the ultraviolet aging resistant biodegradable mulching film can absorb ultraviolet light and release the ultraviolet light with harmless energy, and the heat released in the process can increase a certain temperature for the growth and development of crops, so that the growth process of the crops is accelerated. In addition, the addition of the ultraviolet absorbent can relieve the degradation degree of the biodegradable mulching film so as to prolong the coverage period of the biodegradable mulching film material, which is helpful for improving the crop yield. Therefore, the use of ultraviolet absorbers and anti-ultraviolet aging biodegradable mulching films has important significance for the development of agricultural production.
Currently, the organic ultraviolet absorbers commonly used mainly comprise four major classes of benzophenones, benzotriazoles, triazines and salicylates, and the main problems of the ultraviolet absorbers are small molecular weight, easy volatilization and migration, and are mostly applied to traditional plastics. Therefore, an ultraviolet absorber which is suitable for a degradable material and has stable action and effect and a biodegradable mulching film which resists ultraviolet aging are products which are urgently needed in the market.
Disclosure of Invention
Aiming at the problems of small molecular weight, easy volatilization and migration, poor action effect and the like of the existing ultraviolet absorbent, the invention provides the ultraviolet absorbent, which can enlarge the molecular weight of the ultraviolet absorbent, increase the flexible chain segments of molecules to reduce volatilization and migration, increase the matching degree with degradation materials, widen the absorption of ultraviolet wave bands and provide more scientific basis for the research and development and application of the ultraviolet absorbent and the ultraviolet aging resistant biodegradable mulch film.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
the invention provides an ultraviolet aging resistant biodegradable material containing an ultraviolet absorbent, such as master batch or film.
The invention further provides a preparation method of the ultraviolet aging resistant biodegradable material.
The ultraviolet aging resistant biodegradable material is mainly used for preparing ultraviolet aging resistant biodegradable mulching films, and can also be used for building chemical materials such as pipes, plates, linings and the like.
The ultraviolet absorber has the following structural formula,wherein Z is->Or (b)
The recommended ultraviolet absorber has the following structural formula:
the preparation method of the ultraviolet aging resistant biodegradable material comprises the following steps:
the ultraviolet absorber, the polymer resin and the opening agent are respectively prepared according to the weight percentage of 1-5:500-2000: mixing in a proportion of 0-1, carrying out melt extrusion, and granulating to obtain master batches; or mixing the master batch with polymer resin and an opening agent, uniformly stirring, and then blow molding to form a film, and melt-extruding the film into pipes, plates, linings and the like.
The weight percentage of the ultraviolet aging resistant biodegradable master batch containing the ultraviolet absorber, the polymer resin and the opening agent is 1:0.5-2:0.8-2:0.0005-0.002; the opening agent is erucamide, polylactic acid, polymethyl ethylene carbonate or polyvinyl chloride. The polymer resin is a degradable plastic PBAT: PLA polylactic acid, PPC polymethyl carbonate, etc., and the opening agent is oleamide, stearic acid amide, naphthalene acid amide or mono-stearic acid acyl, etc.
The melt extrusion adopts a single-twin-screw extruder or a twin-screw extruder, and the extrusion temperature is 150-180 ℃; the film forming by blowing is carried out by adopting an extrusion film blowing machine, and the blowing temperature is 150-180 ℃.
The method can be further described by way of example: 20kg of master batch was taken and uniformly mixed with 19.68kg of PBAT and 0.32kg of a vent agent to obtain a blow molding compound. And (3) blowing the mixture into a film by using a film blowing machine to obtain the ultraviolet aging resistant biodegradable mulch film with the thickness of 10+/-1 mu m. Wherein the melt blown film is divided into three temperature areas, the temperature of the first area is 160 ℃, the temperature of the second area is 170 ℃, and the temperature of the third area is 180 DEG C
The ultraviolet absorbent of the invention has simple and convenient synthesis method, is economical, is suitable for industrial production, and can prepare ultraviolet aging resistant biodegradable materials such as particles or films, etc. The absorbent can effectively absorb multi-band ultraviolet light, so that the aging degree of the biodegradable mulching film is weakened, and the functional period of the biodegradable mulching film is prolonged.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIGS. 1 (a) (before use) and (b) (after field application for 33 days) are UV-visible absorption spectra of the UV-curable mulch films of examples 1-6.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without any inventive effort, are intended to be within the scope of the invention.
Example 1
The embodiment provides an ultraviolet aging resistant biodegradable mulching film, which comprises the following components in parts by weight:
PBAT:99.19 parts of a powder of a mixture of two or more,
ultraviolet absorber: 0.001 part of the total weight of the composition,
and (3) an opening agent: 0.8 part (erucamide is selected).
The preparation method of the ultraviolet aging resistant biodegradable mulching film comprises the following steps:
(1) Synthesizing an ultraviolet absorber; the first step: bisphenol A (5.0 g,21.9 mmol) and anhydrous potassium carbonate (18.3 g,132.6 mmol) were dissolved in 50ml anhydrous N, N-dimethylformamide DMF or methyl tert-butyl ether and stirred at 25℃for 30min; then 1-bromo-6-chlorohexane (10.8 g,54.5 mmol) was added dropwise to the reaction system, the temperature was raised to 70℃and the reaction was completed after 9 hours. Cooling the reaction solution to 25 ℃, pouring the reaction solution into ice water for quenching, fully stirring, and extracting with ethyl acetate; the separated organic phase is dried with anhydrous sodium sulfate and concentrated to obtain crude product of the first step reaction product. Purifying the crude product obtained in the first step by silica gel column chromatography, wherein the solvent is n-hexane and ethyl acetate, so as to obtain a pure product of the reaction product in the first step. And a second step of: tropolone (3.95 g,32.4 mmol) and anhydrous potassium carbonate (4.45 g,32.2 mmol) were dissolved in 50ml anhydrous DMF and 18-crown-6 (0.142 g,0.54 mmol) and stirred at 25℃for 30min; then (7.14 g,15.4 mmol) of the pure product (6.28 g,15.5 mmol) obtained in the first step was added dropwise to the reaction system, the temperature was increased to 90℃and the reaction was completed after 9 hours. Cooling the reaction solution to 25 ℃, pouring the reaction solution into ice water for quenching, fully stirring, and extracting with ethyl acetate; the separated organic phase is dried with anhydrous sodium sulfate and concentrated to obtain crude product of the second step reaction product. Purifying the crude product obtained in the second step by silica gel column chromatography, wherein the solvent is n-hexane and ethyl acetate, so as to obtain the ultraviolet absorbent. The structural formula of the ultraviolet absorber is as follows:
(2) Preparing master batch; mixing 40g of the ultraviolet absorbent in the step (1) with 20kg of granular PBAT, and uniformly mixing by a high-speed stirrer to obtain a mixture, wherein the stirring time is 3min. Putting the mixture into a double-screw extruder, setting the temperature of the double-screw extruder to 160 ℃, carrying out melt blending on the mixture by the extruder, and granulating after cooling by air or water to room temperature to obtain the master batch.
(3) Preparing an anti-ultraviolet aging biodegradable mulching film; taking 20kg of master batch obtained in the step (2), and uniformly mixing with 19.68kg of PBAT and 0.32kg of opening agent to obtain a blow molding compound. And (3) blowing the mixture into a film by using a film blowing machine to obtain the ultraviolet aging resistant biodegradable mulch film with the thickness of 10+/-1 mu m. Wherein the melt blown film is divided into three temperature areas, the temperature of the first area is 160 ℃, the temperature of the second area is 170 ℃, and the temperature of the third area is 180 ℃.
The ultraviolet absorption spectrum of the ultraviolet aging resistant biodegradable mulch film in example 1 is shown in fig. 1, and the control is a common biodegradable mulch film (PBAT). As can be seen from FIG. 1, the anti-ultraviolet aging biodegradable mulch film can effectively absorb ultraviolet light in the wave band of 230-320 nm. And compared with the control, the ultraviolet aging resistant biodegradable mulch film in the embodiment 1 has higher ultraviolet light absorption degree.
Example 2
The embodiment provides an ultraviolet aging resistant biodegradable mulching film, which comprises the following components:
PBAT:99.19 parts
Ultraviolet absorber: 0.0015 part
And (3) an opening agent: 0.8 part
The preparation process of the ultraviolet absorber, the master batch and the ultraviolet aging resistant biodegradable mulching film in this embodiment is the same as that of embodiment 1, wherein the addition proportion of the ultraviolet absorber in the ultraviolet aging resistant biodegradable mulching film is 0.15%.
The ultraviolet absorption spectrum of the ultraviolet aging resistant biodegradable mulch film in example 2 is shown in fig. 1. As can be seen from FIG. 1, the anti-ultraviolet aging biodegradable mulch film can effectively absorb ultraviolet light in the wave band of 230-320 nm. And compared with the comparison, the ultraviolet aging resistant biodegradable mulching film in the embodiment 2 has higher ultraviolet light absorption.
Example 3
The embodiment provides an ultraviolet aging resistant biodegradable mulching film, which comprises the following components:
PBAT:99.19 parts
Ultraviolet absorber: 0.002 parts
And (3) an opening agent: 0.8 part
The preparation process of the ultraviolet absorber, the master batch and the ultraviolet aging resistant biodegradable mulch film in this embodiment is the same as that of embodiment 1, wherein the addition proportion of the ultraviolet absorber in the ultraviolet aging resistant biodegradable mulch film is 0.2%.
The ultraviolet absorption spectrum of the ultraviolet aging resistant biodegradable mulch film in example 3 is shown in fig. 1. As can be seen from FIG. 1, the anti-ultraviolet aging biodegradable mulch film can effectively absorb ultraviolet light in the wave band of 230-320 nm. And the anti-ultraviolet aging biodegradable mulching film in the embodiment 3 has higher absorptivity to ultraviolet light than the contrast.
Example 4
The embodiment provides an ultraviolet aging resistant biodegradable mulching film, which comprises the following components:
PBAT:99.19 parts
Ultraviolet absorber: 0.001 part
And (3) an opening agent: 0.8 part
The process for preparing the master batch and the ultraviolet aging resistant biodegradable mulch film in this example is the same as that in example 1, except that the ultraviolet absorber is different, wherein the synthesis process of the ultraviolet absorber changes 1-bromo-6-chlorohexane in example 1 into 1-bromo-4-chlorobutane, and the molecular formula of the obtained ultraviolet absorber is [ C 37 H 40 O 6 ]The structural formula is as follows:
the ultraviolet absorption spectrum of the ultraviolet aging resistant biodegradable mulch film in example 4 is shown in fig. 1. As can be seen from FIG. 1, the anti-ultraviolet aging biodegradable mulch film can effectively absorb ultraviolet light in the wave band of 230-320 nm. And the ultraviolet aging resistant biodegradable mulching film in the embodiment can absorb ultraviolet light more effectively relative to a control.
Example 5
The embodiment provides an ultraviolet aging resistant biodegradable mulching film, which comprises the following components:
PBAT:99.19 parts
Ultraviolet absorber: 0.001 part
And (3) an opening agent: 0.8 part (erucamide)
The preparation process of the master batch and the ultraviolet aging resistant biodegradable mulch film in the embodiment is the same as that of the embodiment 1, except that the ultraviolet absorbent is different, wherein the preparation method of the ultraviolet absorbent is as follows:
tropolone (5.0 g,41 mmol) and anhydrous potassium carbonate (6.5 g,47.1 mmol) were dissolved in 50ml anhydrous DMF and stirred at 25℃for 30min; dibromo-paraxylene (5.0 g,18.9 mmol) was further added to the reaction system, the temperature was increased to 90℃and the reaction was completed after 6 hours. Cooling the reaction solution to 25 ℃, pouring the reaction solution into ice water for quenching, fully stirring and filtering; washing the filter cake with a large amount of water, and drying to obtain the ultraviolet absorbent. The molecular formula of the obtained ultraviolet absorbent is [ C ] 22 H 18 O 4 ]The structural formula is as follows:
the ultraviolet absorption spectrum of the ultraviolet aging resistant biodegradable mulch film in example 5 is shown in fig. 1. As can be seen from FIG. 1, the anti-ultraviolet aging biodegradable mulch film can effectively absorb ultraviolet light in the wave band of 230-320 nm. And compared with the comparison, the ultraviolet aging resistant biodegradable mulching film in the embodiment has stronger ultraviolet light absorption capacity.
Example 6
The embodiment provides an ultraviolet aging resistant biodegradable mulching film, which comprises the following components:
PBAT:99.19 parts
Ultraviolet absorber: 0.001 part
And (3) an opening agent: 0.8 part (erucamide)
The process for preparing the master batch and the ultraviolet aging resistant biodegradable mulch film in this embodiment is the same as that in embodiment 1, except that the ultraviolet absorber is different, wherein the ultraviolet absorber is a commercially available substance, and the molecular formula thereof is [ C ] 7 H 6 O 2 ]The structural formula is as follows:
the ultraviolet absorption spectrum of the ultraviolet aging resistant biodegradable mulch film in example 6 is shown in fig. 1. As can be seen from FIG. 1, the anti-ultraviolet aging biodegradable mulch film can effectively absorb ultraviolet light in the wave band of 230-320 nm. And the ultraviolet aging resistant biodegradable mulching film in the embodiment 6 has higher ultraviolet light absorption degree than that of a control.
The field application effect of the ultraviolet aging resistant biodegradable mulch film (experimental group) in examples 1-6 was analyzed and evaluated using fresh corn as a test crop and pure PBAT mulch film (PBAT) as a control group. The soil conditions and field management measures of the two groups are consistent. The functional period of each mulching film in the experimental group and the control group and the fresh weight yield of the fresh corn are shown in table 1.
TABLE 1
| Treatment of | Mulch film functional period (Tian) | Fresh weight of corn (kg)/667 m 2 |
| Pure PBAT | 40 | 1458.8±48.8 |
| Example 1 | 48 | 1582.1±19.1 |
| Example 2 | 46 | 1580.3±18.4 |
| Example 3 | 46 | 1581.6±18.8 |
| Example 4 | 45 | 1573.5±10.2 |
| Example 5 | 43 | 1525.6±30.0 |
| Example 6 | 41 | 1527.7±19.1 |
As shown in Table 1, the functional period of each mulch film in examples 1-6 was increased to a different extent as compared with the pure PBAT mulch film, indicating that the biodegradable mulch films in examples 1-6 were more resistant to ultraviolet aging; among them, the mulch film of example 1 had the longest functional period, indicating that the ultraviolet absorber added in the mulch film had the strongest ability to absorb ultraviolet light. For the fresh weight of corn, the fresh weight of corn covered with the anti-ultraviolet aging biodegradable film is significantly higher than that of corn covered with the pure PBAT film, especially example 1, which shows that the introduction of ultraviolet absorbent in the PBAT film is beneficial to the growth and development of corn and the improvement of yield.
While the foregoing embodiments have been described in detail and with reference to the present invention, it will be apparent to one skilled in the art that modifications and improvements can be made based on the teachings disclosed herein without departing from the spirit and scope of the invention.
Claims (4)
1. A material containing an ultraviolet absorber, characterized in that the material is an anti-ultraviolet absorberThe ultraviolet aging biodegradation master batch, mulch film or other building chemical materials are pipes, plates or linings, the ultraviolet absorbent contains cycloolefin, benzene ring and ketone group, and the general molecular formula of the structure isWherein Z ism＝3-8。
2. The ultraviolet absorber-containing material of claim 1, wherein the ultraviolet absorber has the structural formula:
3. a method for preparing a material containing an ultraviolet absorber, characterized in that the ultraviolet absorber, the polymer resin and the opening agent according to claim 1 or 2 are respectively added according to the weight percentage of 0.001-0.005:98.95-99.99: mixing in a proportion of 0-1, carrying out melt extrusion, and granulating to obtain master batches; or mixing the master batch with polymer resin and an opening agent, uniformly stirring, and then blow molding to form a film, wherein the weight percentage of the master batch to the polymer resin and the opening agent is 1:0.5-2:0.8-2:0.0005-0.002; the opening agent is erucamide, oleamide or stearic acid amide; the polymer resin is degradable plastic PBAT, PLA biodegradable plastic or PPC polymethyl carbonate.
4. The method for producing a material containing an ultraviolet absorber according to claim 3, wherein the melt extrusion is performed by using a twin-screw extruder, and the extrusion temperature of the twin-screw extruder is 150 to 180 ℃; the film forming by blowing is carried out by adopting an extrusion film blowing machine, and the blowing temperature is 150-180 ℃.
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Citations (1)
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| CN102238983A (en) * | 2008-06-25 | 2011-11-09 | 巴斯夫欧洲公司 | Use of benzotropolone derivatives as uv absorbers and antioxidants and their use in sunscreens and/or cosmetic compositions |
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| US20110060061A1 (en) * | 2009-09-04 | 2011-03-10 | Smink Jeffrey S | Masterbatch composition having a high polymer processing aid |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102238983A (en) * | 2008-06-25 | 2011-11-09 | 巴斯夫欧洲公司 | Use of benzotropolone derivatives as uv absorbers and antioxidants and their use in sunscreens and/or cosmetic compositions |
Non-Patent Citations (1)
| Title |
|---|
| Rasshofer, Werner.Ligand structure and complexation. XL. Noncyclic crown ether type esters and their metal ion complexes.Chemische Berichte.1979,第112卷(第6期),第2095-2119页. * |
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