CN114369340A - Material containing ultraviolet absorbent and preparation method thereof - Google Patents
Material containing ultraviolet absorbent and preparation method thereof Download PDFInfo
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- CN114369340A CN114369340A CN202111394491.9A CN202111394491A CN114369340A CN 114369340 A CN114369340 A CN 114369340A CN 202111394491 A CN202111394491 A CN 202111394491A CN 114369340 A CN114369340 A CN 114369340A
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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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- C—CHEMISTRY; METALLURGY
- 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
- 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
- C08K5/16—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
Abstract
The invention relates to a material containing ultraviolet absorbent, a preparation method and application. The general molecular formula of the structure of the ultraviolet absorbent is
Wherein
Description
Technical Field
The invention relates to an anti-ultraviolet aging biodegradable material, such as master batch or film, which is an anti-ultraviolet aging biodegradable material capable of effectively absorbing multiband ultraviolet light.
Background
Ultraviolet absorbers are a class of substances that can absorb the ultraviolet light from sunlight or fluorescent light sources, convert it to harmless energy and release it without changing itself. A large amount of harmful ultraviolet light (the wavelength is mainly concentrated at 280-400nm) contained in sunlight is irradiated on the surface of the biodegradable mulch film material to cause the performance reduction and the function degradation of the material, and the damage of the ultraviolet light to the biodegradable mulch film material can be relieved to a certain extent by using an ultraviolet absorbent.
The anti-ultraviolet aging biodegradable mulching film is a functional agricultural film which can reduce the damage of ultraviolet light to the mulching film material by introducing an ultraviolet absorbent so as to prolong the service life of the mulching film. The ultraviolet absorbent in the anti-ultraviolet aging 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 can be accelerated. In addition, the addition of the ultraviolet absorbent can relieve the degradation degree of the biodegradable mulching film so as to prolong the covering period of the biodegradable mulching film material, which is beneficial to the improvement of the crop yield. Therefore, the use of the ultraviolet absorbent and the anti-ultraviolet aging biodegradable mulching film has important significance for the development of agricultural production.
At present, the commonly used organic ultraviolet absorbers mainly comprise four major classes of benzophenones, benzotriazoles, triazines and salicylates, and the ultraviolet absorbers have the main problems of small molecular weight, easy volatilization and migration and are mostly applied to traditional plastics. Therefore, the ultraviolet absorbent and the anti-ultraviolet aging biodegradable mulching film which are suitable for degrading materials and have stable action effect are products which are urgently needed in the market.
Disclosure of Invention
Aiming at the problems of poor effect and the like caused by small molecular weight, easy volatilization and migration of the existing ultraviolet absorbent, the invention provides the ultraviolet absorbent, which can expand the molecular weight of the ultraviolet absorbent, increase the flexible chain segment of molecules to reduce volatilization and migration, increase the matching degree with degradation materials, widen the absorption of ultraviolet bands and provide more scientific basis for the research and development and application of the ultraviolet absorbent and the anti-ultraviolet aging biodegradable mulching film.
In order to achieve the purpose, the 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 also aims to provide a preparation method of the ultraviolet aging resistant biodegradable material.
The invention also aims at that the anti-ultraviolet aging biodegradable material is mainly used for preparing anti-ultraviolet aging biodegradable mulching films and can also be used for building chemical materials, such as pipes, plates, linings and the like.
The ultraviolet absorbent has the following structural formula,
wherein Z is
Or
The recommended uv absorbers have the following structural formula:
the preparation method of the anti-ultraviolet aging biodegradable material comprises the following steps:
respectively mixing an ultraviolet absorbent, a polymer resin and an opening agent according to the weight percentage of 1-5: 500-2000: mixing at a ratio of 0-1, melt extruding, and granulating to obtain master batch; or mixing the master batch with polymer resin and an opening agent, uniformly stirring, blow-molding to form a film, and performing melt extrusion to form a pipe, a plate, a lining and the like.
The weight percentage of the ultraviolet aging resistant biodegradable master batch containing the ultraviolet absorbent to the polymer resin and the opening agent is 1: 0.5-2: 0.8-2: 0.0005-0.002; the above-mentioned 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 and the like, and the opening agent is oleamide, stearic acid amide, naphthoic acid amide, or monostearate and the like.
The melt extrusion adopts a single-screw extruder or a double-screw extruder, and the extrusion temperature is 150-180 ℃; the blow molding film forming is realized by adopting an extrusion film blowing machine, and the blow molding temperature is 150-180 ℃.
The method can be further described by way of example: 20kg of master batch is uniformly mixed with 19.68kg of PBAT and 0.32kg of opening agent to obtain a blow molding mixture. And (3) blowing the mixture into a film by using a film blowing machine to obtain the anti-ultraviolet aging biodegradable mulching film with the thickness of 10 +/-1 mu m. Wherein the melt blown film is divided into three temperature zones, the temperature of the first zone is 160 ℃, the temperature of the second zone is 170 ℃, and the temperature of the third zone is 180 DEG C
The ultraviolet absorbent of the invention has simple and convenient synthesis method, is economic and is suitable for industrial production, and can be used for preparing ultraviolet aging resistant biodegradable materials such as particles or films. The absorbent can effectively absorb multiband ultraviolet light, thereby weakening the aging degree of the biodegradable mulching film and being beneficial to prolonging the functional period of the biodegradable mulching film.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIGS. 1(a) (before use) and (b) (after 33 days of field mulching) are UV-VIS absorption spectra of UV-resistant mulch films of examples 1-6.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without any inventive step, shall fall within the scope of the present invention.
Example 1
The embodiment provides an anti-ultraviolet aging biodegradable mulching film which comprises the following components in parts by weight:
PBAT: 99.19 parts of (a) to (b),
ultraviolet absorber: 0.001 part by weight of a reaction kettle,
an opening agent: 0.8 portion (erucamide is selected).
The preparation method of the anti-ultraviolet aging biodegradable mulching film comprises the following steps:
(1) synthesizing an ultraviolet absorbent; the first step is as follows: bisphenol A (5.0g,21.9mmol) and anhydrous potassium carbonate (18.3g,132.6mmol) were dissolved in 50ml of anhydrous N, N-dimethylformamide DMF or methyl tert-butyl ether and stirred at 25 ℃ for 30 min; then, 1-bromo-6-chlorohexane (10.8g,54.5mmol) was added dropwise to the reaction system, the temperature was raised to 70 ℃ and the reaction was terminated after 9 hours. Cooling the reaction solution to 25 ℃, pouring the reaction solution into ice water for quenching, fully stirring the reaction solution, and extracting the reaction solution by using ethyl acetate; after the liquid separation, the organic phase is dried by anhydrous sodium sulfate and concentrated to obtain a crude product of the reaction product in the first step. And (3) purifying the crude product obtained in the first step by silica gel column chromatography, wherein the solvents are n-hexane and ethyl acetate, and the pure product of the reaction product in the first step is obtained. The second step is that: cycloheptatrienol ketone (3.95 g,32.4mmol) and anhydrous potassium carbonate (4.45g,32.2mmol) were dissolved in 50ml anhydrous DMF and 18-crown-6 (0.142g,0.54mmol) and stirred at 25 ℃ for 30 min; then (7.14g,15.4mmol) the pure product (6.28g,15.5mmol) obtained in the first step was added dropwise to the reaction system, the temperature was raised to 90 ℃ and the reaction was terminated after 9 hours. Cooling the reaction solution to 25 ℃, pouring the reaction solution into ice water for quenching, fully stirring, and extracting by using ethyl acetate; after the liquid separation, the organic phase is dried by anhydrous sodium sulfate and concentrated to obtain a crude product of a reaction product in the second step. And purifying the crude product obtained in the second step by silica gel column chromatography, wherein the solvents are n-hexane and ethyl acetate to obtain the ultraviolet absorbent. The structural formula of the ultraviolet absorbent is as follows:
(2) preparing a master batch; and (3) mixing 40g of the ultraviolet absorbent in the step (1) with 20kg of granular PBAT, and uniformly mixing the mixture by using a high-speed mixer for 3 min. And putting the mixture into a double-screw extruder, setting the temperature of the double-screw extruder at 160 ℃, melting and blending the mixture uniformly by the extruder, and then carrying out air cooling or water cooling to room temperature and then carrying out grain cutting to obtain the master batch.
(3) Preparing an anti-ultraviolet aging biodegradable mulching film; and (3) uniformly mixing 20kg of the master batch obtained in the step (2), 19.68kg of PBAT and 0.32kg of an opening agent to obtain a blow molding mixture. And (3) blowing the mixture into a film by using a film blowing machine to obtain the anti-ultraviolet aging biodegradable mulching film with the thickness of 10 +/-1 mu m. The melt blown film is divided into three temperature zones, wherein the temperature of the first zone is 160 ℃, the temperature of the second zone is 170 ℃, and the temperature of the third zone is 180 ℃.
The ultraviolet absorption spectrum of the ultraviolet aging resistant biodegradable mulching film in example 1 is shown in fig. 1, and the control is common biodegradable mulching film (PBAT). As can be seen from FIG. 1, the anti-ultraviolet aging biodegradable mulch film can effectively absorb ultraviolet light in the 230-320nm waveband. And compared with the control, the ultraviolet light absorption degree of the ultraviolet aging resistant biodegradable mulching film in the example 1 is higher.
Example 2
The embodiment provides an anti-ultraviolet aging biodegradable mulching film which comprises the following components:
PBAT: 99.19 parts
Ultraviolet absorber: 0.0015 part
An opening agent: 0.8 portion of
The preparation process of the ultraviolet absorbent, the master batch and the ultraviolet aging resistant biodegradable mulching film in the embodiment is the same as that of the embodiment 1, wherein the addition ratio of the ultraviolet absorbent in the ultraviolet aging resistant biodegradable mulching film is 0.15%.
The ultraviolet absorption spectrum of the anti-ultraviolet aging 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 230-320nm waveband. And compared with the control, the anti-ultraviolet aging biodegradable mulching film in the example 2 has higher ultraviolet light absorption.
Example 3
The embodiment provides an anti-ultraviolet aging biodegradable mulching film which comprises the following components:
PBAT: 99.19 parts
Ultraviolet absorber: 0.002 part
An opening agent: 0.8 portion of
The preparation process of the ultraviolet absorbent, the master batch and the ultraviolet aging resistant biodegradable mulching film in the embodiment is the same as that of the embodiment 1, wherein the addition ratio of the ultraviolet absorbent in the ultraviolet aging resistant biodegradable mulching film is 0.2%.
The ultraviolet absorption spectrum of the anti-ultraviolet aging biodegradable mulch film in example 3 is shown in figure 1. As can be seen from FIG. 1, the anti-ultraviolet aging biodegradable mulch film can effectively absorb ultraviolet light in the 230-320nm waveband. And the anti-ultraviolet aging biodegradable mulching film in the embodiment 3 has higher absorption of ultraviolet light compared with a control.
Example 4
The embodiment provides an anti-ultraviolet aging biodegradable mulching film which comprises the following components:
PBAT: 99.19 parts
Ultraviolet absorber: 0.001 portion
An opening agent: 0.8 portion of
The preparation process of the master batch and the anti-ultraviolet aging biodegradable mulch film in the embodiment is the same as that of the embodiment 1, except that the ultraviolet absorbent is different, wherein the synthesis process of the ultraviolet absorbent is to replace 1-bromo-6-chlorohexane in the embodiment 1 with 1-bromo-4-chlorobutane, and the obtained ultraviolet absorbent hasThe molecular formula is [ C37H40O6]The structure formula is as follows:
the ultraviolet absorption spectrum of the anti-ultraviolet aging 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 230-320nm waveband. And the anti-ultraviolet aging biodegradable mulch film in the embodiment can absorb ultraviolet light more effectively compared with a control.
Example 5
The embodiment provides an anti-ultraviolet aging biodegradable mulching film which comprises the following components:
PBAT: 99.19 parts
Ultraviolet absorber: 0.001 portion
An opening agent: 0.8 portion (erucamide is selected)
The preparation process of the master batch and the anti-ultraviolet aging biodegradable mulch film in the embodiment is the same as that of the embodiment 1, and the difference is that the ultraviolet absorbent is different, wherein the preparation method of the ultraviolet absorbent is as follows:
cycloheptatrienol ketone (5.0g,41mmol) and anhydrous potassium carbonate (6.5g,47.1mmol) were dissolved in 50ml anhydrous DMF and stirred at 25 ℃ for 30 min; dibromo-p-xylene (5.0g,18.9mmol) was added to the reaction system, the temperature was raised to 90 ℃ and the reaction was terminated after 6 hours. Cooling the reaction liquid to 25 ℃, pouring the reaction liquid 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 ]22H18O4]The structural formula is as follows:
the ultraviolet absorption spectrum of the ultraviolet aging resistant biodegradable mulching film in example 5 is shown in figure 1. As can be seen from FIG. 1, the anti-ultraviolet aging biodegradable mulch film can effectively absorb ultraviolet light in the 230-320nm waveband. And compared with the control, the anti-ultraviolet aging biodegradable mulching film in the embodiment has stronger ultraviolet light absorption capacity.
Example 6
The embodiment provides an anti-ultraviolet aging biodegradable mulching film which comprises the following components:
PBAT: 99.19 parts
Ultraviolet absorber: 0.001 portion
An opening agent: 0.8 portion (erucamide is selected)
The preparation process of the master batch and the anti-ultraviolet aging biodegradable mulch film in this example is the same as that of example 1, except that the ultraviolet absorber is different, wherein the ultraviolet absorber is a commercially available substance and has a molecular formula of [ C [ ]7H6O2]The structural formula is as follows:
the ultraviolet absorption spectrum of the ultraviolet aging resistant biodegradable mulching 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 230-320nm waveband. And the ultraviolet aging resistant biodegradable mulching film in the embodiment 6 has higher absorption degree of ultraviolet light compared with the control.
The field application effect of the anti-ultraviolet aging biodegradable mulch film (experimental group) in examples 1-6 was analyzed and evaluated with fresh corn as the test crop and pure PBAT mulch film (PBAT) as the control group. The soil conditions and field management measures of the two groups are consistent. The functional period of each mulching film and the fresh weight yield of fresh corn in the experimental group and the control group are shown in table 1.
TABLE 1
| Treatment of | Functional stage of mulch film (sky) | Fresh weight of corn (kg)/667m2 |
| 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 can be seen from Table 1, compared with the pure PBAT mulching film, the functional periods of the mulching films in the examples 1-6 are increased to different degrees, which indicates that the biodegradable mulching films in the examples 1-6 have stronger ultraviolet aging resistance; the mulch film in example 1 has the longest functional period, which indicates that the added ultraviolet absorber has the strongest ability to absorb ultraviolet light. For the fresh weight of the corn, the fresh weight of the corn covered with the ultraviolet aging resistant biodegradable film is obviously higher than that of the corn covered with the pure PBAT film, especially in example 1, which shows that the introduction of the ultraviolet absorbent into the PBAT mulching film is beneficial to the growth and development of the corn and the improvement of the yield.
Although the present invention has been described in detail with respect to the above embodiments, it will be understood by those skilled in the art that modifications or improvements based on the disclosure of the present invention may be made without departing from the spirit and scope of the invention, and these modifications and improvements are within the spirit and scope of the invention.
Claims (6)
1. A material containing an ultraviolet absorber, wherein the ultraviolet absorber contains a cyclic olefin, a benzene ring and a ketone group, and has a general structural formula
Wherein Z is
m＝3-8。
2. The uv absorber-containing material according to claim 1, wherein the uv absorber has the following structural formula:
3. the material containing ultraviolet absorber of claim 1, 2, which is an ultraviolet aging resistant biodegradable masterbatch or mulch film.
4. A method for producing a material containing an ultraviolet absorber as claimed in claim 1, 2 or 3, wherein the ultraviolet absorber, the polymer resin and the opening agent are added in an amount of 0.001 to 0.005: 98.95-99.99: mixing at a ratio of 0-1, melt extruding, and granulating to obtain master batch; or mixing the master batch with polymer resin and an opening agent, uniformly stirring, and blow-molding to form a film, wherein the weight percentage of the master batch to the polymer resin to the opening agent is 1: 0.5-2: 0.8-2: 0.0005-0.002; the above-mentioned opening agent is erucamide, polylactic acid, polymethyl ethylene carbonic ester or polyvinyl chloride; the polymer resin is degradable plastic PBAT: PLA biodegradable plastics, PPC poly methyl carbonate or polylactic acid; the opening agent is oleic acid amide, stearic acid amide, naphthoic acid amide or menthyl stearate.
5. The method for preparing a material containing UV absorber according to claim 4, wherein the melt extrusion is performed by using a twin-screw extruder, and the extrusion temperature of the twin-screw extruder is 150-180 ℃; the blow molding film forming is realized by adopting an extrusion film blowing machine, and the blow molding temperature is 150-180 ℃.
6. The UV absorber-containing material according to claim 1, wherein the UV aging resistant biodegradable material is a UV aging resistant biodegradable masterbatch, an agricultural mulch, a building chemical material for pipes, plates or linings.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110060061A1 (en) * | 2009-09-04 | 2011-03-10 | Smink Jeffrey S | Masterbatch composition having a high polymer processing aid |
| 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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2021
- 2021-11-23 CN CN202111394491.9A patent/CN114369340B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US20110060061A1 (en) * | 2009-09-04 | 2011-03-10 | Smink Jeffrey S | Masterbatch composition having a high polymer processing aid |
Non-Patent Citations (1)
| Title |
|---|
| RASSHOFER, WERNER: "Ligand structure and complexation. XL. Noncyclic crown ether type esters and their metal ion complexes", vol. 112, no. 6, pages 2095 - 2119 * |
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