CN114525017A - High-toughness composition of semi-aromatic carbon dioxide-based copolymer and preparation method thereof - Google Patents
High-toughness composition of semi-aromatic carbon dioxide-based copolymer and preparation method thereof Download PDFInfo
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- CN114525017A CN114525017A CN202111118683.7A CN202111118683A CN114525017A CN 114525017 A CN114525017 A CN 114525017A CN 202111118683 A CN202111118683 A CN 202111118683A CN 114525017 A CN114525017 A CN 114525017A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/32—General preparatory processes using carbon dioxide
- C08G64/34—General preparatory processes using carbon dioxide and cyclic ethers
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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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2237—Oxides; Hydroxides of metals of titanium
- C08K2003/2241—Titanium dioxide
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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
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/005—Additives being defined by their particle size in general
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/06—Biodegradable
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/10—Transparent films; Clear coatings; Transparent materials
Abstract
The invention provides a high-toughness composition of a semi-aromatic carbon dioxide-based copolymer and a preparation method thereof. The composition is prepared from the semi-aromatic carbon dioxide-based copolymer, PBAT, a filler and a compatibilizer, the vitrification temperature of the composition is increased by regulating the structure of a molecular chain segment in the semi-aromatic carbon dioxide-based copolymer and other methods, the biodegradability of the composition is improved, and the biodegradable material which has good transparency, strong light transmittance, mechanical property, processability and usability and meets the practical application is obtained.
Description
Technical Field
The invention belongs to the technical field of C08G63/64, and particularly relates to a high-toughness semi-aromatic carbon dioxide-based copolymer composition and a preparation method thereof.
Background
Propylene oxide and carbon dioxide copolymers have biodegradability and excellent gas barrier properties, but their low glass transition temperature limits their applications. PBAT is a plastic with excellent biodegradability and higher heat resistance, but the tensile strength of PBAT is not high due to the molecular structure of PBAT, so that the application of PBAT in the field of high-strength films is limited.
Chinese patent CN101724251B discloses a blend of PPC (propylene oxide and carbon dioxide copolymer) and PBAT, but the tensile strength of the prepared blend is not improved much, and the glass transition temperature of the blend is lower. It is still not satisfactory for use in special fields. Based on this, the applicant has proposed a high toughness composition of a semi-aromatic carbon dioxide based copolymer and a method for preparing the same, resulting in a degradable high toughness composition having good tensile strength.
Disclosure of Invention
The invention provides a high-toughness composition of a semi-aromatic carbon dioxide-based copolymer, which comprises 1-99 parts of the semi-aromatic carbon dioxide-based copolymer, 1-99 parts of PBAT and 0.1-20 parts of a functional auxiliary agent.
In a preferred embodiment, the raw materials comprise 20-50 parts by weight of semi-aromatic carbon dioxide-based copolymer, 50-80 parts by weight of PBAT and 1-15 parts by weight of functional auxiliary agent.
In a preferred embodiment, the tensile strength of the PBAT is 12-25 MPa.
In a preferred embodiment, the tensile strength of the PBAT is 20-25 MPa.
In a preferred embodiment, the PBAT is purchased from polyester ltd, tunny, blue, n.i. n.t. TH 801T.
In a preferred embodiment, the semi-aromatic carbon dioxide-based copolymer is prepared as follows:
(1) adding phthalic anhydride, partial propylene oxide and a catalyst into a reactor, introducing carbon dioxide, and reacting;
(2) and adding the rest propylene oxide, continuing to react, and after the reaction is finished, drying in vacuum to obtain the semi-aromatic carbon dioxide-based copolymer.
In a preferred embodiment, part of the propylene oxide in step (1) accounts for 30 to 80% of the total mass of the propylene oxide.
In a preferred embodiment, part of the propylene oxide in step (1) is 80% of the total mass of the propylene oxide.
In a preferred embodiment, the molar ratio of phthalic anhydride to propylene oxide is (1-5): (5-12).
In a preferred embodiment, the molar ratio of phthalic anhydride to propylene oxide is 1.5: 10.
In a preferred embodiment, the catalyst is a combination free of tetrabutylammonium halide and triethylboron.
In a preferred embodiment, the molar ratio of tetrabutylammonium halide to triethylboron is 1: 8.
in a preferred embodiment, the molar ratio of propylene oxide to metal-free two-component catalyst is 440: 1.
in the experimental process, the applicant finds that in the system, propylene oxide is added twice in the process of preparing the semi-aromatic carbon dioxide-based copolymer, and particularly when part of propylene oxide accounts for 80% of the total mass of propylene oxide in the step (1), the glass transition temperature of propylene carbonate can be increased and the tensile strength of the propylene carbonate can be increased under the condition of improving the random distribution of soft segments and hard segments in molecular chain segments of the prepared propylene carbonate.
In a preferred embodiment, the functional assistant is at least one selected from the group consisting of a compatibilizer, a lubricant, a filler, an opening agent, and a mold release agent.
In a preferred embodiment, the compatibilizer is selected from at least one of ethylene butyl acrylate, hexamethylene diisocyanate, polycaprolactone, tetrabutyl titanate, an epoxy chain extender, and an oxazoline chain extender.
In a preferred embodiment, the mass ratio of the compatibilizer to the semi-aromatic carbon dioxide-based copolymer is 1: (20-60).
In a preferred embodiment, the mass ratio of the compatibilizer to the semi-aromatic carbon dioxide-based copolymer is 1: 20.
In a preferred embodiment, the mass ratio of the semi-aromatic carbon dioxide-based copolymer to the PBAT is (3-5): (5-7).
In a preferred embodiment, the mass ratio of the semi-aromatic carbon dioxide-based copolymer to PBAT is 3: 7.
In the application, the high-toughness composition is prepared from the specific semi-aromatic carbon dioxide-based copolymer and the specific PBAT according to the specific raw material proportion, so that the melt viscosity of the semi-aromatic carbon dioxide-based copolymer is improved, the compatibility of the semi-aromatic carbon dioxide-based copolymer and the specific PBAT is increased, and the stability of the composition is improved due to the addition of the compatibilizer. The composition obtained by the application shows good flexibility, mechanical processing performance and excellent biodegradability.
In a preferred embodiment, the filler is selected from at least one of silica, ground calcium carbonate, titanium dioxide, zinc oxide.
In a preferred embodiment, the filler is titanium dioxide.
In a preferred embodiment, the titanium dioxide is a silane coupling agent-modified titanium dioxide.
In a preferred embodiment, the titanium dioxide has a particle size of 15 nm.
In a preferred embodiment, the silane coupling agent is selected from at least one of an alkenyl silane coupling agent, an aminosilane coupling agent, and an epoxy silane coupling agent.
In a preferred embodiment, the silane coupling agent modified titanium dioxide is a compound substance of aminosilane coupling agent modified titanium dioxide and alkenyl silane coupling agent modified titanium dioxide.
In a preferred embodiment, the mass ratio of the aminosilane coupling agent-modified titanium dioxide to the alkenylsilane coupling agent-modified titanium dioxide is (2.5 to 4.8): 1.
in a preferred embodiment, the mass ratio of the aminosilane coupling agent-modified titanium dioxide to the alkenylsilane coupling agent-modified titanium dioxide is 3.5: 1.
in the present application, the kinds of the aminosilane coupling agent and the alkenylsilane coupling agent are not particularly limited, and 3-aminopropyltriethoxysilane and vinyltris (2-methoxyethoxy) silane are preferable.
In a preferred embodiment, the mass ratio of filler to PBAT is 1: (5-15).
In a preferred embodiment, the mass ratio of filler to PBAT is 1: 7.
In the experimental process, the applicant finds that the toughness of the composition can be improved by adding the modified titanium dioxide with the specific particle size, and the compatibility degree and the temperature resistance of the composition can also be improved. The applicant speculates that the possible reason is that the modified titanium dioxide can be used as a connecting point of the semi-aromatic carbon dioxide-based copolymer and the PBAT in the system, so that the composition is promoted to be compatible, meanwhile, the composition is promoted to form a three-dimensional space structure, and the toughness and the tensile strength of the composition are improved.
In a second aspect, the present invention provides a process for the preparation of a high toughness composition of a semi-aromatic carbon dioxide based copolymer comprising the steps of: dehydrating and drying the semi-aromatic carbon dioxide-based copolymer, the PBAT and the functional auxiliary agent at 55-70 ℃, putting the dehydrated and dried semi-aromatic carbon dioxide-based copolymer, the PBAT and the functional auxiliary agent into a mixing machine, uniformly mixing, adding the mixture into a double-screw extruder, and extruding at the temperature of 100-160 ℃ to obtain the high-toughness composition.
Compared with the prior art, the invention has the following beneficial effects:
according to the invention, the composition obtained by blending the carbonic acid copolymer, the PBAT, the compatibilizer and the modified titanium dioxide is promoted to form a three-dimensional structure by regulating and controlling the structure of a molecular chain segment in the semi-aromatic carbon dioxide-based copolymer and adding the modified titanium dioxide, the glass transition temperature of the composition is increased, the toughness of the composition is increased, the biodegradability of the composition is increased, and the biodegradable material which is good in transparency, strong in light transmittance, and meets the requirements of mechanical properties, processability and usability in practical application is obtained.
Detailed Description
Example 1
The invention provides a high-toughness composition of a semi-aromatic carbon dioxide-based copolymer, which is prepared from the raw materials of 30 parts of the semi-aromatic carbon dioxide-based copolymer, 70 parts of PBAT, 1.5 parts of a compatibilizer and 10 parts of a filler.
The compatibilizer is an epoxy compound chain-extending compatibilizer, and specifically is glycidyl methacrylate.
The filler is silane coupling agent modified titanium dioxide, the silane coupling agent modified titanium dioxide is a compound substance of 3-aminopropyl triethoxysilane modified titanium dioxide and vinyl tri (2-methoxyethoxy) silane modified titanium dioxide, and the mass ratio of the 3-aminopropyl triethoxysilane modified titanium dioxide to the vinyl tri (2-methoxyethoxy) silane modified titanium dioxide is 3.5: 1.
The preparation method of the silane coupling agent modified titanium dioxide comprises the following steps: dispersing 5g of titanium dioxide in 50ml of absolute ethyl alcohol, performing ultrasonic treatment for 10min, adding 3g of silane coupling agent, keeping the temperature at 70 ℃, and performing ultrasonic treatment for 1.5h to obtain the modified titanium dioxide.
The titanium dioxide is purchased from Beijing Deke island gold science and technology Co., Ltd, and the particle size is 15 nm.
The semi-aromatic carbon dioxide-based copolymer is prepared according to the following steps:
(1) adding phthalic anhydride, epoxypropane accounting for 80% of the total mass of the epoxypropane, tetrabutylammonium bromide and triethylboron into a reactor, introducing carbon dioxide to the pressure of 1.1MPa, and reacting for 6 hours at 70 ℃;
(2) and adding propylene oxide accounting for 20 percent of the total mass of the propylene oxide, continuously reacting for 2 hours at 70 ℃, and after the reaction is finished, drying in vacuum to obtain the semi-aromatic carbon dioxide-based copolymer.
Wherein the molar ratio of phthalic anhydride to propylene oxide is 1.5: 10; the molar ratio of the propylene oxide to the metal-free two-component catalyst is 440: 1; the molar ratio of tetrabutylammonium bromide to triethylboron is 1: 8.
the PBAT is purchased from polyester Co., Ltd, blue Shantun, Xinjiang, and has the model number TH 801T.
In a second aspect, the present invention provides a process for the preparation of a high toughness composition of a semi-aromatic carbon dioxide based copolymer comprising the steps of: dehydrating and drying the semi-aromatic carbon dioxide-based copolymer, the PBAT and the compatibilizer at 60 ℃, putting the dehydrated and dried semi-aromatic carbon dioxide-based copolymer, the PBAT and the compatibilizer into a mixer, uniformly mixing, adding the mixture into a double-screw extruder, and extruding at 140 ℃ to obtain the high-toughness composition.
Example 2
The invention provides a high-toughness composition of a semi-aromatic carbon dioxide-based copolymer, which is prepared from 40 parts of the semi-aromatic carbon dioxide-based copolymer, 60 parts of PBAT, 2 parts of a compatibilizer and 8.57 parts of a filler.
The compatibilizer is an oxazoline chain-extending compatibilizer which is purchased from Shanghai Va-New Material Co., Ltd and has the model of RAS-1005.
The filler is silane coupling agent modified titanium dioxide, the silane coupling agent modified titanium dioxide is a compound substance of 3-aminopropyl triethoxysilane modified titanium dioxide and vinyl tri (2-methoxyethoxy) silane modified titanium dioxide, and the mass ratio of the 3-aminopropyl triethoxysilane modified titanium dioxide to the vinyl tri (2-methoxyethoxy) silane modified titanium dioxide is 3.5: 1.
The preparation method of the silane coupling agent modified titanium dioxide comprises the following steps: dispersing 5g of titanium dioxide in 50ml of absolute ethyl alcohol, performing ultrasonic treatment for 10min, adding 3g of silane coupling agent, keeping the temperature at 70 ℃, and performing ultrasonic treatment for 1.5h to obtain the modified titanium dioxide.
The titanium dioxide is purchased from Beijing Deke island gold science and technology Co., Ltd, and the particle size is 15 nm.
The semi-aromatic carbon dioxide-based copolymer is prepared according to the following steps:
(1) adding phthalic anhydride, epoxypropane accounting for 80% of the total mass of the epoxypropane, tetrabutylammonium bromide and triethylboron into a reactor, introducing carbon dioxide to the pressure of 1.1MPa, and reacting for 6 hours at 70 ℃;
(2) and adding propylene oxide accounting for 20 percent of the total mass of the propylene oxide, continuously reacting for 2 hours at 70 ℃, and after the reaction is finished, drying in vacuum to obtain the semi-aromatic carbon dioxide-based copolymer.
Wherein the molar ratio of phthalic anhydride to propylene oxide is 1.5: 10; the molar ratio of the propylene oxide to the metal-free two-component catalyst is 440: 1; the molar ratio of tetrabutylammonium bromide to triethylboron is 1: 8.
the PBAT is purchased from polyester Co., Ltd, blue Shantun, Xinjiang, and has the model number TH 801T.
In a second aspect, the present invention provides a process for the preparation of a high toughness composition of a semi-aromatic carbon dioxide based copolymer comprising the steps of: dehydrating and drying the semi-aromatic carbon dioxide-based copolymer, the PBAT and the compatibilizer at 60 ℃, putting the dehydrated and dried semi-aromatic carbon dioxide-based copolymer, the PBAT and the compatibilizer into a mixer, uniformly mixing, adding the mixture into a double-screw extruder, and extruding at 140 ℃ to obtain the high-toughness composition.
Example 3
The invention provides a high-toughness composition of a semi-aromatic carbon dioxide-based copolymer, which is prepared from the raw materials of 30 parts of the semi-aromatic carbon dioxide-based copolymer, 70 parts of PBAT and 1.5 parts of a compatibilizer.
The compatibilizer is an epoxy compound chain-extending compatibilizer, and specifically is glycidyl methacrylate.
The semi-aromatic carbon dioxide-based copolymer is prepared according to the following steps:
(1) adding phthalic anhydride, epoxypropane accounting for 80% of the total mass of the epoxypropane, tetrabutylammonium bromide and triethylboron into a reactor, introducing carbon dioxide to the pressure of 1.1MPa, and reacting for 6 hours at 70 ℃;
(2) and adding propylene oxide accounting for 20 percent of the total mass of the propylene oxide, continuously reacting for 2 hours at 70 ℃, and after the reaction is finished, drying in vacuum to obtain the semi-aromatic carbon dioxide-based copolymer.
Wherein the molar ratio of phthalic anhydride to propylene oxide is 1.5: 10; the molar ratio of the propylene oxide to the metal-free two-component catalyst is 440: 1; the molar ratio of tetrabutylammonium bromide to triethylboron is 1: 8.
the PBAT is purchased from polyester Co., Ltd, blue Shantun, Xinjiang, and has the model number TH 801T.
In a second aspect, the present invention provides a process for the preparation of a high toughness composition of a semi-aromatic carbon dioxide based copolymer comprising the steps of: dehydrating and drying the semi-aromatic carbon dioxide-based copolymer, the PBAT and the compatibilizer at 60 ℃, putting the dehydrated and dried semi-aromatic carbon dioxide-based copolymer, the PBAT and the compatibilizer into a mixer, uniformly mixing, adding the mixture into a double-screw extruder, and extruding at 140 ℃ to obtain the high-toughness composition.
Performance testing
The high-toughness composition prepared in the example is prepared according to a method commonly used by a person skilled in the art, the tensile property and the elongation at break of the sample are tested according to the national standard GB/T1040, and the biodegradability is tested according to the national standard GB/T19277. The data are recorded in table 1.
TABLE 1
Claims (10)
1. The high-toughness composition of the semi-aromatic carbon dioxide-based copolymer is characterized by comprising 1-99 parts of the semi-aromatic carbon dioxide-based copolymer, 1-99 parts of PBAT and 0.1-20 parts of a functional auxiliary agent by weight.
2. The high toughness composition of claim 1, wherein said starting materials comprise, by weight, 20-50 parts of semi-aromatic carbon dioxide based copolymer, 50-80 parts of PBAT, and 1-15 parts of functional additives.
3. A high toughness composition according to any of claims 1-2, characterised in that the tensile strength of the PBAT is 12-25 MPa.
4. A high toughness composition according to claim 3, characterized in that the tensile strength of the PBAT is 20-25 MPa.
5. A high toughness composition according to any one of claims 1 to 2, wherein said functional auxiliary agent is selected from at least one of compatibilizers, lubricants, fillers, opening agents, mold release agents.
6. The high toughness composition of claim 5, wherein said compatibilizer is selected from at least one of ethylene butyl acrylate, hexamethylene diisocyanate, polycaprolactone, tetrabutyl titanate, epoxy chain extenders, oxazoline chain extenders.
7. The high toughness composition of claim 5, wherein said filler is selected from at least one of silica, ground calcium carbonate, titanium dioxide, zinc oxide.
8. The high toughness composition of claim 7, wherein said titanium dioxide is a silane coupling agent modified titanium dioxide.
9. The high toughness composition of claim 8, wherein said silane coupling agent is selected from at least one of the group consisting of alkenyl silane coupling agents, aminosilane coupling agents, and epoxy silane coupling agents.
10. A process for the preparation of a high toughness composition according to any one of claims 1 to 9, characterized by the following steps: dehydrating and drying the semi-aromatic carbon dioxide-based copolymer, the PBAT and the functional auxiliary agent at 55-70 ℃, putting the dehydrated and dried semi-aromatic carbon dioxide-based copolymer, the PBAT and the functional auxiliary agent into a mixer, uniformly mixing, adding the mixture into a double-screw extruder, and extruding at the temperature of 100-160 ℃ to obtain the high-toughness composition.
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| CN202111118683.7A CN114525017B (en) | 2021-09-24 | 2021-09-24 | Semi-aromatic carbon dioxide based copolymer high-toughness composition and preparation method thereof |
| PCT/CN2022/119498 WO2023045850A1 (en) | 2021-09-24 | 2022-09-19 | High-toughness composition of semi-aromatic carbon dioxide-based copolymer and preparation method therefor |
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| CN115521591A (en) * | 2022-11-07 | 2022-12-27 | 山东联欣环保科技有限公司 | High-toughness composition of carbon dioxide-based quadripolymer and preparation method thereof |
| WO2023045850A1 (en) * | 2021-09-24 | 2023-03-30 | 山东联欣环保科技有限公司 | High-toughness composition of semi-aromatic carbon dioxide-based copolymer and preparation method therefor |
| CN116021850A (en) * | 2023-03-30 | 2023-04-28 | 山东联欣环保科技有限公司 | Barrier biodegradable cigarette packaging film and preparation process thereof |
| CN117024941A (en) * | 2023-10-08 | 2023-11-10 | 山东联欣环保科技有限公司 | Carbon dioxide-based biodegradable barrier composition |
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| WO2023045850A1 (en) * | 2021-09-24 | 2023-03-30 | 山东联欣环保科技有限公司 | High-toughness composition of semi-aromatic carbon dioxide-based copolymer and preparation method therefor |
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| CN115521591B (en) * | 2022-11-07 | 2023-01-31 | 山东联欣环保科技有限公司 | High-toughness composition of carbon dioxide-based quadripolymer and preparation method thereof |
| CN116021850A (en) * | 2023-03-30 | 2023-04-28 | 山东联欣环保科技有限公司 | Barrier biodegradable cigarette packaging film and preparation process thereof |
| CN117024941A (en) * | 2023-10-08 | 2023-11-10 | 山东联欣环保科技有限公司 | Carbon dioxide-based biodegradable barrier composition |
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| WO2023045850A1 (en) | 2023-03-30 |
| CN114525017B (en) | 2023-04-28 |
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