CN117417514A - Anthracene-2, 6-dicarboxylic acid modified PBAT degradation material, preparation method and application thereof - Google Patents
Anthracene-2, 6-dicarboxylic acid modified PBAT degradation material, preparation method and application thereof Download PDFInfo
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- CN117417514A CN117417514A CN202311737528.2A CN202311737528A CN117417514A CN 117417514 A CN117417514 A CN 117417514A CN 202311737528 A CN202311737528 A CN 202311737528A CN 117417514 A CN117417514 A CN 117417514A
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- dicarboxylic acid
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- XAAYMWLCUICVSL-UHFFFAOYSA-N anthracene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC3=CC(C(=O)O)=CC=C3C=C21 XAAYMWLCUICVSL-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 239000000463 material Substances 0.000 title claims abstract description 31
- 230000015556 catabolic process Effects 0.000 title claims abstract description 26
- 238000006731 degradation reaction Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 229920001896 polybutyrate Polymers 0.000 title claims abstract 15
- 238000005886 esterification reaction Methods 0.000 claims abstract description 39
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 36
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims abstract description 36
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 19
- 239000001361 adipic acid Substances 0.000 claims abstract description 18
- 235000011037 adipic acid Nutrition 0.000 claims abstract description 18
- 229920000642 polymer Polymers 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 239000007806 chemical reaction intermediate Substances 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 14
- 239000006227 byproduct Substances 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 8
- 229920006280 packaging film Polymers 0.000 claims description 4
- 239000012785 packaging film Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002156 mixing Methods 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000007599 discharging Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- -1 Polybutylene terephthalate-adipate Polymers 0.000 description 3
- 229920001707 polybutylene terephthalate Polymers 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006126 semicrystalline polymer Polymers 0.000 description 1
Classifications
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/185—Acids containing aromatic rings containing two or more aromatic rings
- C08G63/187—Acids containing aromatic rings containing two or more aromatic rings containing condensed aromatic rings
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
-
- 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
-
- 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
-
- 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
- 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
- Y02W90/10—Bio-packaging, e.g. packing containers made from renewable resources or bio-plastics
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
The invention relates to the technical field of polymer preparation, in particular to an anthracene-2, 6-dicarboxylic acid modified PBAT degradation material, a preparation method and application thereof. The method comprises the steps of mixing adipic acid, terephthalic acid, anthracene-2, 6-dicarboxylic acid, 1, 4-butanediol and a catalyst according to mass ratio, heating to perform esterification reaction to obtain an esterification reaction intermediate, adding the catalyst, heating to perform polycondensation reaction to obtain the anthracene-2, 6-dicarboxylic acid molecular structure modified PBAT polymer. The degradation material has the advantages of improving the elastic modulus and the tensile strength of the PBAT, widening the application range of the PBAT and the like while ensuring the original excellent toughness and the impact resistance of the PBAT, and can be widely applied to the technical field of polymer preparation.
Description
Technical Field
The invention relates to the technical field of polymer preparation, in particular to an anthracene-2, 6-dicarboxylic acid modified PBAT degradation material, a preparation method and application thereof.
Background
Polybutylene terephthalate-adipate (PBAT) is a semi-crystalline polymer. The PBAT has better ductility of polybutylene adipate (PBA) and strength of polybutylene terephthalate (PBT), has better heat resistance, has decomposition temperature higher than 300 ℃, is soft and transparent in texture, belongs to compostable degradable materials and environment-friendly materials, can effectively resist white pollution, has better ductility and heat resistance, and has good impact property and elongation at break, and is widely applied to disposable packaging films and agricultural films. The disadvantage is that the crystallinity is relatively poor, the crystallinity is low, the strength is poor, and the elastic modulus is not high.
Most of the current studies are based on blending modification of PBAT. And (3) polymerization modification, namely, regulating and controlling the proportion and distribution of rigid and flexible groups and the topological structure of the polymer chain through the design and customization of the polymer chain structure, so that the strength of the biodegradable polymer is improved. Thus, the PBAT is modified into a new direction by copolymerization.
Disclosure of Invention
First, the technical problem to be solved
The invention mainly aims at solving the problems that PBAT (poly (butylene terephthalate)) crystallization performance is poor, crystallinity is low, strength is poor and elastic modulus is low.
(II) technical scheme
In order to achieve the above purpose, the invention provides a preparation method of an anthracene-2, 6-dicarboxylic acid modified PBAT degradation material, which comprises the steps of mixing adipic acid, terephthalic acid, anthracene-2, 6-dicarboxylic acid, 1, 4-butanediol and a catalyst according to mass ratio, heating to perform esterification reaction to obtain an esterification reaction intermediate, adding the catalyst, heating to perform polycondensation reaction to obtain the anthracene-2, 6-dicarboxylic acid molecular structure modified PBAT polymer.
Further, the catalyst for the esterification reaction is tetrabutyl titanate, and the addition amount of the tetrabutyl titanate for the esterification reaction is 0.2-0.6% of the total mass of adipic acid, terephthalic acid and anthracene-2, 6-dicarboxylic acid.
Further, the catalyst for the polycondensation reaction is stannous octoate, and the adding amount of the catalyst stannous octoate in the polycondensation stage is 0.75% of the total mass of adipic acid, terephthalic acid and anthracene-2, 6-dicarboxylic acid.
Further, the raw materials are respectively 146g of adipic acid, 378g of 1, 4-butanediol, 166g of terephthalic acid, 266g of anthracene-2, 6-dicarboxylic acid, 1.16-3.46g of tetrabutyl titanate and 4.3g of stannous octoate.
Further, the alcohol-acid ratio of the esterification reaction is 1.4:1 or 1.5:1.
Further, in the step of carrying out the esterification reaction, heating to 190 ℃ to carry out the esterification reaction, and when the water yield of byproducts of the esterification reaction reaches 98% of the theoretical water yield, treating the reaction as the end; in the step of polycondensation, the temperature is raised to 250 ℃ to carry out polycondensation, and the reaction time is 2h.
In order to achieve the aim, the invention provides application of the anthracene-2, 6-dicarboxylic acid modified PBAT degradation material obtained by the preparation method in packaging films and agricultural films.
In order to achieve the above purpose, the invention provides an anthracene-2, 6-dicarboxylic acid modified PBAT degradation material, which is prepared by the preparation method, and has the following structural general formula:
。
(III) beneficial effects
Compared with the prior art, the anthracene-2, 6-dicarboxylic acid modified PBAT degradation material, the preparation method and the application thereof have the advantages of improving the elastic modulus and the tensile strength of PBAT, widening the application range of PBAT and the like while ensuring the original excellent toughness and the impact resistance of PBAT, and can be widely applied to the technical field of polymer preparation.
Detailed Description
The present invention will be described in further detail below: the present embodiment is implemented on the premise of the technical solution of the present invention, and a detailed implementation is given, but the scope of protection of the present invention is not limited to the following embodiments.
According to the preparation method of the anthracene-2, 6-dicarboxylic acid modified PBAT degradation material, adipic acid, terephthalic acid, anthracene-2, 6-dicarboxylic acid, 1, 4-butanediol and a catalyst are added into a reaction kettle according to mass ratio, the mixture is heated to 190 ℃ for esterification reaction, when the water yield of byproducts of the esterification reaction reaches 98% of theoretical water yield, the reaction is regarded as the end, an esterification reaction intermediate is obtained, the catalyst is added, the temperature is raised to 250 ℃ for polycondensation reaction, and the reaction time is 2 hours, so that the anthracene-2, 6-dicarboxylic acid molecular structure modified PBAT polymer is obtained.
The structural general formula of the copolymer is shown as follows:
。
the catalyst for the esterification reaction is tetrabutyl titanate, and the addition amount of the tetrabutyl titanate for the esterification reaction is 0.2-0.6% of the total mass of adipic acid, terephthalic acid and anthracene-2, 6-dicarboxylic acid.
The catalyst for the polycondensation reaction is stannous octoate, and the adding amount of the stannous octoate in the polycondensation stage is 0.75% of the total mass of adipic acid, terephthalic acid and anthracene-2, 6-dicarboxylic acid.
The raw materials are 146g of adipic acid, 378g of 1, 4-butanediol, 166g of terephthalic acid, 266g of anthracene-2, 6-dicarboxylic acid, 1.16-3.46g of tetrabutyl titanate and 4.3g of stannous octoate according to the proportioning mass.
The alcohol-acid ratio of the esterification reaction is 1.4:1 or 1.5:1.
The anthracene-2, 6-dicarboxylic acid modified PBAT degradation material obtained by the preparation method not only has originally excellent toughness and impact resistance, but also greatly improves the elastic modulus and tensile strength of the PBAT, so that the material can be widely applied to the fields of packaging films and agricultural films.
Example 1
According to the preparation method of the anthracene-2, 6-dicarboxylic acid modified PBAT degradation material, 146g of adipic acid, 166g of terephthalic acid, 266g of anthracene-2, 6-dicarboxylic acid, 378g of 1, 4-butanediol and 1.16g of tetrabutyl titanate are added into a reaction kettle, are heated to 190 ℃ after being mixed for esterification reaction, when the byproduct water yield of the esterification reaction reaches 98% of the theoretical water yield, the esterification reaction intermediate is obtained after the reaction is finished, then 4.3g of stannous octoate is added, the temperature is raised to 250 ℃ for vacuum polycondensation reaction, and the reaction time is 2 hours, so that the anthracene-2, 6-dicarboxylic acid molecular structure modified PBAT polymer is obtained. Stopping stirring, closing vacuum, introducing nitrogen, pressurizing and discharging.
Example 2
According to the preparation method of the anthracene-2, 6-dicarboxylic acid modified PBAT degradation material, 146g of adipic acid, 166g of terephthalic acid, 266g of anthracene-2, 6-dicarboxylic acid, 378g of 1, 4-butanediol and 1.73g of tetrabutyl titanate are added into a reaction kettle, the mixture is heated to 190 ℃ for esterification reaction, when the byproduct water yield of the esterification reaction reaches 98% of the theoretical water yield, the reaction is finished, an esterification reaction intermediate is obtained, then 4.3g of stannous octoate is added, the temperature is raised to 250 ℃ for vacuum polycondensation reaction, and the reaction time is 2 hours, so that the anthracene-2, 6-dicarboxylic acid molecular structure modified PBAT polymer is obtained. Stopping stirring, closing vacuum, introducing nitrogen, pressurizing and discharging.
Example 3
According to the preparation method of the anthracene-2, 6-dicarboxylic acid modified PBAT degradation material, 146g of adipic acid, 166g of terephthalic acid, 266g of anthracene-2, 6-dicarboxylic acid, 378g of 1, 4-butanediol and 2.31g of tetrabutyl titanate are added into a reaction kettle, are heated to 190 ℃ after being mixed for esterification reaction, when the byproduct water yield of the esterification reaction reaches 98% of the theoretical water yield, the esterification reaction intermediate is obtained after the reaction is finished, then 4.3g of stannous octoate is added, the temperature is raised to 250 ℃ for vacuum polycondensation reaction, and the reaction time is 2 hours, so that the anthracene-2, 6-dicarboxylic acid molecular structure modified PBAT polymer is obtained. Stopping stirring, closing vacuum, introducing nitrogen, pressurizing and discharging.
Example 4
According to the preparation method of the anthracene-2, 6-dicarboxylic acid modified PBAT degradation material, 146g of adipic acid, 166g of terephthalic acid, 266g of anthracene-2, 6-dicarboxylic acid, 378g of 1, 4-butanediol and 2.89g of tetrabutyl titanate are added into a reaction kettle, are heated to 190 ℃ after being mixed for esterification reaction, when the byproduct water yield of the esterification reaction reaches 98% of the theoretical water yield, the esterification reaction intermediate is obtained after the reaction is finished, then 4.3g of stannous octoate is added, the temperature is raised to 250 ℃ for vacuum polycondensation reaction, and the reaction time is 2 hours, so that the anthracene-2, 6-dicarboxylic acid molecular structure modified PBAT polymer is obtained. Stopping stirring, closing vacuum, introducing nitrogen, pressurizing and discharging.
Example 5
According to the preparation method of the anthracene-2, 6-dicarboxylic acid modified PBAT degradation material, 146g of adipic acid, 166g of terephthalic acid, 266g of anthracene-2, 6-dicarboxylic acid, 378g of 1, 4-butanediol and 3.47g of tetrabutyl titanate are added into a reaction kettle, are heated to 190 ℃ after being mixed for esterification reaction, when the byproduct water yield of the esterification reaction reaches 98% of the theoretical water yield, the esterification reaction intermediate is obtained after the reaction is finished, then 4.3g of stannous octoate is added, the temperature is raised to 250 ℃ for vacuum polycondensation reaction, and the reaction time is 2 hours, so that the anthracene-2, 6-dicarboxylic acid molecular structure modified PBAT polymer is obtained. Stopping stirring, closing vacuum, introducing nitrogen, pressurizing and discharging.
The performance of the anthracene-2, 6-dicarboxylic acid modified PBAT degradation materials prepared in examples one to five of the invention is compared with the following table:
from the above table, the elastic modulus of the anthracene-2, 6-dicarboxylic acid modified PBAT degradation material is obviously improved by 54% compared with that of the PBAT polymer. The introduction of anthracene-2, 6-dicarboxylic acid improves the strength of the material and overcomes the defect of insufficient strength of PBAT.
The foregoing is merely a preferred embodiment of the present invention, and it should be noted that it will be apparent to those skilled in the art that modifications and variations can be made without departing from the technical principles of the present invention, and these modifications and variations should also be regarded as the scope of the invention.
Claims (8)
1. A preparation method of an anthracene-2, 6-dicarboxylic acid modified PBAT degradation material is characterized in that adipic acid, terephthalic acid, anthracene-2, 6-dicarboxylic acid, 1, 4-butanediol and a catalyst are mixed according to mass ratio, then the mixture is heated for esterification reaction to obtain an esterification reaction intermediate, then the catalyst is added and heated for polycondensation reaction to obtain the anthracene-2, 6-dicarboxylic acid molecular structure modified PBAT polymer.
2. The method for preparing an anthracene-2, 6-dicarboxylic acid modified PBAT degradation material as claimed in claim 1, wherein the catalyst of the esterification reaction is tetrabutyl titanate, and the addition amount of the tetrabutyl titanate of the esterification reaction is 0.2-0.6% of the total mass of adipic acid, terephthalic acid and anthracene-2, 6-dicarboxylic acid.
3. The method for preparing an anthracene-2, 6-dicarboxylic acid modified PBAT degradation material as claimed in claim 2, wherein the catalyst for the polycondensation reaction is stannous octoate, and the adding amount of the stannous octoate in the polycondensation stage is 0.75% of the total mass of adipic acid, terephthalic acid and anthracene-2, 6-dicarboxylic acid.
4. The method for preparing an anthracene-2, 6-dicarboxylic acid modified PBAT degradation material according to claim 3, wherein the raw materials are respectively 146g of adipic acid, 378g of 1, 4-butanediol, 166g of terephthalic acid, 266g of anthracene-2, 6-dicarboxylic acid, 1.16-3.46g of tetrabutyl titanate and 4.3g of stannous octoate.
5. The method for preparing an anthracene-2, 6-dicarboxylic acid modified PBAT degradation material according to claim 1, wherein the ratio of alcohol acid in the esterification reaction is 1.4:1 or 1.5:1.
6. The method for producing an anthracene-2, 6-dicarboxylic acid modified PBAT degradation material according to claim 1, wherein in the step of conducting the esterification reaction, heating to 190 ℃ to conduct the esterification reaction, and when the byproduct water yield of the esterification reaction reaches 98% of the theoretical water yield, the reaction is regarded as being completed; in the step of polycondensation, the temperature is raised to 250 ℃ to carry out polycondensation, and the reaction time is 2h.
7. Use of an anthracene-2, 6-dicarboxylic acid modified PBAT degradation material obtained by the preparation method of any one of claims 1 to 6 in packaging films, agricultural films.
8. An anthracene-2, 6-dicarboxylic acid modified PBAT degradation material, which is characterized in that the material is prepared by the preparation method in any one of claims 1-6, and has the following structural general formula:
。
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| JP2006053974A (en) * | 2004-08-10 | 2006-02-23 | Hitachi Maxell Ltd | Magnetic recording medium |
| CN104211930A (en) * | 2014-08-31 | 2014-12-17 | 海安南京大学高新技术研究院 | Large-dimension aromatic ring structure-containing polyester for powder coating and preparation method of polyester |
| CN108383983A (en) * | 2018-04-01 | 2018-08-10 | 汕头市龙琪塑料制品有限公司 | A kind of preparation method of anti-oxidation drug bottle |
| CN115417982A (en) * | 2022-10-12 | 2022-12-02 | 万华化学集团股份有限公司 | Preparation method of poly (terephthalic acid) -adipic acid-butanediol copolyester |
| CN115612074A (en) * | 2022-10-17 | 2023-01-17 | 南通天洋新材料有限公司 | Preparation method of biodegradable polyester |
-
2023
- 2023-12-18 CN CN202311737528.2A patent/CN117417514A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006053974A (en) * | 2004-08-10 | 2006-02-23 | Hitachi Maxell Ltd | Magnetic recording medium |
| CN104211930A (en) * | 2014-08-31 | 2014-12-17 | 海安南京大学高新技术研究院 | Large-dimension aromatic ring structure-containing polyester for powder coating and preparation method of polyester |
| CN108383983A (en) * | 2018-04-01 | 2018-08-10 | 汕头市龙琪塑料制品有限公司 | A kind of preparation method of anti-oxidation drug bottle |
| CN115417982A (en) * | 2022-10-12 | 2022-12-02 | 万华化学集团股份有限公司 | Preparation method of poly (terephthalic acid) -adipic acid-butanediol copolyester |
| CN115612074A (en) * | 2022-10-17 | 2023-01-17 | 南通天洋新材料有限公司 | Preparation method of biodegradable polyester |
Non-Patent Citations (1)
| Title |
|---|
| 李红霞: "《耐火材料手册》", 31 January 2021, 冶金工业出版社, pages: 61 * |
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