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Furan glycidyl ether or ester-epoxypropane-CO2 copolymer and preparation thereof

A technology of glycidyl ether and glycidyl ester, which is applied in the field of furan glycidyl ether or ester-propylene oxide-carbon dioxide terpolymer and its preparation, can solve the problem of poor blending compatibility, affecting processing performance and application range , pollute the environment, end-capping agents and other issues, to achieve the effect of favorable utilization

Inactive Publication Date: 2009-05-27
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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Problems solved by technology

Due to the low glass transition temperature (Tg=35-41°C), poor thermal stability, and narrow thermal processing window (130-140°C), "unzip" degradation is prone to occur during thermal processing, which seriously affects the Its processing performance and scope of use
In order to improve the thermal processing performance of PPC and improve its mechanical properties, Chinese patent CN1058408 once proposed the method of blending PPC and nitrile rubber, and Chinese patent CN1371942A then provides the method of blending PPC and poly 3-hydroxyalkanoate It is suggested that although the two methods both play a certain role in improving the thermal processability and mechanical properties of PPC, the former makes PPC products lose their full biodegradability, while the latter is due to the combination of PPC and poly 3-hydroxyalkanoate. The compatibility of blending is poor, and phase separation often occurs at the two-phase interface of the blend, so it is difficult to find a suitable compatibilizer
Dixon believes that carbon dioxide-epoxide copolymer aliphatic polycarbonates can be capped in solution with organic compounds reactive with hydroxyl groups to eliminate chain terminal hydroxyl groups that cause "unzipper" reactions and improve their thermal stability ( US4,066,630; US4,104,264; US4,145,525), although this method improves the heat resistance of PPC, it is difficult to be adopted in industrial production because of increasing the complexity and production cost of the process
Liu Jingjiang etc. used the method of melt blending to end-cap PPC with maleic anhydride (Acta Polymer Sinica, 6, 895-898, 2003), which greatly improved the thermal stability of PPC, but there was maleic anhydride in this end-capping method. Defects that are volatile and pollute the environment during the melt capping process and unreacted capping agents are easy to precipitate on the surface during processing
At present, there are no literature and patent reports on the ternary copolymerization of furan glycidyl ether or ester as the third monomer with carbon dioxide and propylene oxide

Method used

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  • Furan glycidyl ether or ester-epoxypropane-CO2 copolymer and preparation thereof
  • Furan glycidyl ether or ester-epoxypropane-CO2 copolymer and preparation thereof
  • Furan glycidyl ether or ester-epoxypropane-CO2 copolymer and preparation thereof

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Experimental program
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Effect test

preparation Embodiment 1

[0033] at a purity of 99.99% N 2 Add 0.0004885mol Y (CCl 3 COO) 3 , 20ml1, 3-dioxolane and 0.004885mol glycerol, to be Y (CCl 3 COO) 3 After all dissolved, slowly add 0.00977mol ZnEt dropwise to the preparation bottle 2 , ZnEt 2 It is advisable to control the reaction temperature at 35-45°C for the dropping speed. ZnEt 2 After the dropwise addition, after no gas is released, place the preparation bottle in a constant temperature bath for aging. The aging conditions are: the temperature of the constant temperature bath is 60°C; the frequency of mechanical oscillation is 150 times / min; the amplitude is 40mm; A total of 2 hours was carried out to obtain a white suspension liquid which was a rare earth three-way catalyst.

preparation Embodiment 2

[0035] The synthesis of furyl methyl glycidyl ether, in the there-necked flask equipped with electric stirrer, thermometer and constant pressure dropping funnel, add 7.6mol epichlorohydrin, 800mL sodium hydroxide solution (50%w / w), and 0.076mol tetra-tert-butylammonium bisulfate, and then 3.8mol of purified furanmethanol was dropped into the above-mentioned three-necked flask at a rate of 6mL / min under a constant pressure dropping funnel under strong stirring at 400rpm, and the temperature of the control system did not exceed 20°C , After reacting for 4 hours, the reaction solution was washed with distilled water until neutral, and the obtained organic phase was dried for 24 hours with 60 g of anhydrous magnesium sulfate, and the dried organic phase was filtered to remove anhydrous magnesium sulfate. The obtained organic phase was distilled off under reduced pressure (2.0KPa) to remove unreacted epichlorohydrin to obtain a crude product of furyl methyl glycidyl ether. The crud...

preparation Embodiment 3

[0037] Synthesis of Glycidyl Tetrahydrofurancarboxylate

[0038] 1) Synthesis of sodium tetrahydrofuran formate, 1.0 mol of sodium hydroxide and 50 ml of distilled water were added into a three-necked flask, then 1.1 mol of tetrahydrofuran formic acid and 80 mL of ethanol (99.5% in purity) were mixed with 6 mL of tetrahydrofuran formic acid through a constant pressure dropping funnel under vigorous stirring at 450 rpm. Drop it into the above-mentioned three-necked flask at a rate of 1 / min, control the temperature of the system at 25°C, and react for 4 hours, distill off ethanol and water under reduced pressure (2.0KPa), wash with acetone three times, each time with 100mL of acetone, at 70°C Dry in vacuo to constant weight. Sodium tetrahydrofuran formate was obtained.

[0039] 2) Synthesis of glycidyl tetrahydrofuran formate, 1.0mol sodium tetrahydrofuran formate, 5.0mol epichlorohydrin, 0.015mol tetra-tert-butylammonium bisulfate are added in a three-necked flask equipped wit...

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Abstract

The invention provides a copolymer of furan-type glycidol ether or furan-type glycidyl ester and propylene oxide and CO2, and a preparation method thereof. The copolymer is prepared by polymerizing the furan-type glycidol ether or furan-type glycidyl ester with the propylene oxide and carbon dioxide under the action of a rare-earth three-way catalyst, wherein the furan-type glycidol ether is furan methyl glycidol ether, 5-methylfuran methyl glycidol ether or tetrahydrofuran methyl glycidol ether; the furan-type glycidyl ester is furan formic-acid glycidyl ester, 5-methylfuran formic-acid glycidyl ester or tetrahydrofuran formic-acid glycidyl ester; and the furan-type glycidol ether or furan-type glycidyl ester can be prepared from furan alcohol or furan acid which is a renewable resource. The highest yield of the terpolymer is up to 4.298*10<3> grams of copolymer per mol of Zn. The initial thermal decomposition temperature of the terpolymer is 256 DEG C, which is 69 DEG C higher than the initial thermal decomposition temperature (187 DEG C) of PPC.

Description

technical field [0001] The invention belongs to a furan glycidyl ether or ester-propylene oxide-carbon dioxide terpolymer and a preparation method thereof. Background technique [0002] The copolymer of carbon dioxide and propylene oxide (PPC) is a fully biodegradable polymer material with excellent gas barrier properties. Due to the low glass transition temperature (Tg=35-41°C), poor thermal stability, and narrow thermal processing window (130-140°C), "unzip" degradation is prone to occur during thermal processing, which seriously affects the Its processing performance and scope of use. In order to improve the thermal processing performance of PPC and improve its mechanical properties, Chinese patent CN1058408 once proposed the method of blending PPC and nitrile rubber, and Chinese patent CN1371942A then provides the method of blending PPC and poly 3-hydroxyalkanoate It is suggested that although the two methods both play a certain role in improving the thermal processabi...

Claims

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Application Information

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IPC IPC(8): C08G64/02C08G64/34
Inventor 乔立军胡玉玺王献红赵晓江王佛松
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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