基于对苯二甲酸丁二醇酯的聚醚酯嵌段共聚物的合成、表征及性能研究
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摘要
本论文介绍了一种通过“一锅法”制备基于对苯二甲酸丁二醇酯的聚醚酯多嵌段聚合物的合成方法。该方法在相对温和的条件下，通过溶液或熔融聚合，采用端基为羟基的聚醚作为大分子引发剂，开环聚合芳香族聚酯环状寡聚物，合成了一系列聚醚酯嵌段共聚物。其中的聚醚为聚乙二醇（PEG）、聚四氢呋喃（PTHF，亦为PTMO）和聚二甲基硅氧烷（PDMS），聚酯为芳香族聚酯聚对苯二甲酸丁二醇酯（PBT）。通过GPC、MALDI-TOF、TGA、DSC、WAXD等多种方法对上述聚合物的结构和性能进行表征，研究结构与性能的相互关系。
主要工作总结如下：
（1）采用双端基为羟基，分子量为10,000Da的PEG为大分子引发剂，钛酸四异丙酯为催化剂，引发对苯二甲酸丁二醇酯环状寡聚物（COBTs）的溶液开环聚合。采用四氯乙烷为溶剂，在较低的聚合反应温度146°C，成功合成了一系列不同分子量的新型PBT-b-PEO-b-PBT三嵌段共聚物。三嵌段共聚物的结构由1H NMR和GPC的表征来证明。TGA的测试结果证明，被PBT封端的PEO的热失重温度提高了30°C左右。由DSC、WAXD的测试结果，观察到嵌段共聚物具有双结晶性能。PBT链段的熔融温度和结晶温度都随PBT含量的增加而升高。并观察到了PEO链段在先结晶的PBT晶片中的受限结晶行为。由POM观察到PBT链段无序结晶的生长形貌。
（2）通过DSC法测试了PBT均聚物和PBT-b-PEO-b-PBT三嵌段共聚物的等温结晶动力学，以及经过等温结晶之后的熔融行为。根据Hoffman-weeks方程估算PBT和PBT-b-PEO-b-PBT三嵌段共聚物的平衡熔点。用Avrami方程描述样品的等温结晶行为，PBT均聚物及嵌段共聚物Avrami指数n都在3.0到4.0之间，说明PEO的加入没有改变PBT结晶的成核机理和生长方式。在相同的过冷度下，PBT均聚物结晶速率最快，并随着PEO含量增加，结晶速率下降。
（3）用两端基为羟基，分子量为1,000Da的PEG为大分子引发剂，钛酸四丁酯为催化剂，引发COBTs熔融状态下的开环聚合反应，合成了(PBT-b-PEO-b-PBT)x多嵌段交替共聚物，并对共聚物的结构和性能进行了表征。采用1H-1H COSY和13C-1HHSQC对共聚物的结构进行了确认，MALDI-TOF的结果也证明共聚物是三嵌段、五嵌段和七嵌段等共聚物组成的混合物。用定量1H NMR的方法计算了共聚物的绝对分子量，考察了聚合反应动力学。并发现当采用较大分子量的PEG时，缩聚反应程度降低。
（4）用两端基为羟基，分子量为2,900Da的PTMO为大分子引发剂，钛酸四丁酯为催化剂，引发COBTs开环聚合反应，“一锅一次投料”熔融缩聚法制备了(PBT-b-PTMO-b-PBT)x多嵌段交替共聚物。通过改变聚合反应时间和催化剂的使用量，利用优化的定量核磁共振氢谱分析方法和GPC测试等方法，研究嵌段共聚物总分子量、各嵌段分子量等随时间的变化规律，考察了聚合反应动力学。结果表明，催化剂的用量对聚合反应速度的影响不大。反应得到的(PBT-b-PTMO-b-PBT)x多嵌段交替共聚物有较好的热稳定性；拉伸性能测试表明，热塑性弹性体的弹性随着共聚物分子量增大而增加。
（5）用两端基为羟基的PDMS为大分子引发剂，钛酸四丁酯为催化剂，引发COBTs熔融状态下的开环聚合反应，合成了PBT-PDMS的多嵌段共聚物。通过改变PDMS的用量，合成了不同PBT链长的PBT-PDMS多嵌段共聚物。通过1H NMR和GPC分析，证明了反应中生成了PBT-PDMS多嵌段共聚物，发现结构不明确。
We present here the one pot, one feeding step synthesis of poly(ether-ester) blockcopolymers with poly(butylene terephthalate)(PBT) as one of the block segment. A seriesof PBT poly(ether ester) triblock and multiblock copolymers with various molecularweight were synthesized by solution and melting ring-opening polymerization (ROP) ofcyclic oligo(butylene terephthalate)s (COBTs), using dihydroxyl end-functionizedpolyethers as macroinitiator, including poly(ethylene glycol)(PEG), poly(tetramethyleneoxide)(PTMO) and poly(dimethyl siloxane)(PDMS). The structure of the multiblockcopolymers is well characterized by nuclear magnetic resonance (NMR) techniques,together with gel permeation chromatography (GPC), and matrix-assisted laser desorptionionization time-of-flight (MALDI-TOF) measurements. The behaviors of these multiblockcopolymers were measured by differential scanning calorimetry (DSC), thermogravimetricanalysis (TGA), wide-angle X-ray diffraction (WAXD), etc.
The main contents are summarized as follows:
(1) We demonstrated a facile synthesis method to novel double crystalline triblockcopolymers for confinement effect studies. Three PBT-b-PEO-b-PBT triblock copolymerswith same PEO but different PBT molecular weights were synthesized by solution ROP ofCOBTs using PEG as macroinitiator and titanium isopropyloxide as catalyst. The structureof copolymers was well characterized by1H NMR and GPC. TGA results revealed that thedecomposition temperature of PEO in triblock copolymers increased about30°C to thesame as PBT copolymers, after being end-capped with PBT polymers. These triblockcopolymers showed double crystalline properties from PBT and PEO blocks, observedfrom DSC and WAXD measurements. The crystallization of PBT blocks showed thestrong confinement effects on PEO blocks due to covalent linkage of PBT blocks withPEO blocks, where the melting and crystallization temperatures and enthalpiescorresponding to PEO blocks decreased significantly with increment of PBT content. Thecrystal morphology was observed by polarized optical microscopy (POM), andamorphous-like spherulites were observed during PBT crystallization.
(2) The isothermal crystallization kineties and melting behaviors after isothermalcrystallization of PBT homopolymer and PBT-b-PEO-b-PBT triblock copolymers wereinvestigated by DSC. The equilibrium melting temperatures of PBT homopolymer andtriblock copolymers were determined by Hoffman-Weeks equation. The deduced Avramiexponent n varies in the range of3.0~4.0, from the analysis of the crystallization kineticdata using the Avrami equation, indicated that the addition of PEO did not alter the crystalgrowth mechanism. The crystallization rates of the PBT-b-PEO-b-PBT triblockcopolymers were decreased with increasing content of PEO.
(3)(PBT-b-PEO-b-PBT)xmultiblock copolymers was were synthesized by the one potmelt polymerization of COBTs using dihydroxyl end group of PEG-1k as themacroinitiator. NMR techniques including1D-quantitative1H NMR、HSQC and1H-1HCOSY have been used to characterize the multiblock copolymer structures This wasfurther confirmed by MALDI-TOF. An improved quantitative1H NMR technique wasapplied to calculate the absolute molecular weights by the chain end and functional groupsestimation. It was found that the polymerization efficiency decreased when the molecularweight of PEO increased to4,000or10,000Da.
(4) A novel method is utilized to synthesize (PBT-b-PTMO-b-PBT)xmultiblockcopolymers by the one pot melt polymerization of COBTs using PTMO as a macroinitiator.The NMR techniques (1D-quantitative1H NMR and1H-1H COSY) have been used tocharacterize and reveal the multiblock copolymer structures and absolute molecularweights. It was found the molecular weights of the multiblock copolymers increasedlinearly with reaction time. The structures of the multiblock copolymers are furthercharacterized by GPC. The polymerization kinetics is slightly affected and incresed withthe catalyst content. These multiblock copolymers show improved thermal stability whencompared to PTMO homopolymers. The mechanical properties test at room temperatureindicates the elongation of the multiblock copolymers increased with molecular weights.
(5) A series of PBT-PDMS multiblock copolymer with different mass content ofPDMS were synthesized by using dihydroxyl end functioned group ofpoly(dimethylsiloxane) as macroinitiator, and their properties are measured.1H NMR andGPC analysis reveals the formation of block copolymers, with very low polymerizationefficiency and unknown block copolymer structure.
主要工作总结如下：
（1）采用双端基为羟基，分子量为10,000Da的PEG为大分子引发剂，钛酸四异丙酯为催化剂，引发对苯二甲酸丁二醇酯环状寡聚物（COBTs）的溶液开环聚合。采用四氯乙烷为溶剂，在较低的聚合反应温度146°C，成功合成了一系列不同分子量的新型PBT-b-PEO-b-PBT三嵌段共聚物。三嵌段共聚物的结构由1H NMR和GPC的表征来证明。TGA的测试结果证明，被PBT封端的PEO的热失重温度提高了30°C左右。由DSC、WAXD的测试结果，观察到嵌段共聚物具有双结晶性能。PBT链段的熔融温度和结晶温度都随PBT含量的增加而升高。并观察到了PEO链段在先结晶的PBT晶片中的受限结晶行为。由POM观察到PBT链段无序结晶的生长形貌。
（2）通过DSC法测试了PBT均聚物和PBT-b-PEO-b-PBT三嵌段共聚物的等温结晶动力学，以及经过等温结晶之后的熔融行为。根据Hoffman-weeks方程估算PBT和PBT-b-PEO-b-PBT三嵌段共聚物的平衡熔点。用Avrami方程描述样品的等温结晶行为，PBT均聚物及嵌段共聚物Avrami指数n都在3.0到4.0之间，说明PEO的加入没有改变PBT结晶的成核机理和生长方式。在相同的过冷度下，PBT均聚物结晶速率最快，并随着PEO含量增加，结晶速率下降。
（3）用两端基为羟基，分子量为1,000Da的PEG为大分子引发剂，钛酸四丁酯为催化剂，引发COBTs熔融状态下的开环聚合反应，合成了(PBT-b-PEO-b-PBT)x多嵌段交替共聚物，并对共聚物的结构和性能进行了表征。采用1H-1H COSY和13C-1HHSQC对共聚物的结构进行了确认，MALDI-TOF的结果也证明共聚物是三嵌段、五嵌段和七嵌段等共聚物组成的混合物。用定量1H NMR的方法计算了共聚物的绝对分子量，考察了聚合反应动力学。并发现当采用较大分子量的PEG时，缩聚反应程度降低。
（4）用两端基为羟基，分子量为2,900Da的PTMO为大分子引发剂，钛酸四丁酯为催化剂，引发COBTs开环聚合反应，“一锅一次投料”熔融缩聚法制备了(PBT-b-PTMO-b-PBT)x多嵌段交替共聚物。通过改变聚合反应时间和催化剂的使用量，利用优化的定量核磁共振氢谱分析方法和GPC测试等方法，研究嵌段共聚物总分子量、各嵌段分子量等随时间的变化规律，考察了聚合反应动力学。结果表明，催化剂的用量对聚合反应速度的影响不大。反应得到的(PBT-b-PTMO-b-PBT)x多嵌段交替共聚物有较好的热稳定性；拉伸性能测试表明，热塑性弹性体的弹性随着共聚物分子量增大而增加。
（5）用两端基为羟基的PDMS为大分子引发剂，钛酸四丁酯为催化剂，引发COBTs熔融状态下的开环聚合反应，合成了PBT-PDMS的多嵌段共聚物。通过改变PDMS的用量，合成了不同PBT链长的PBT-PDMS多嵌段共聚物。通过1H NMR和GPC分析，证明了反应中生成了PBT-PDMS多嵌段共聚物，发现结构不明确。
We present here the one pot, one feeding step synthesis of poly(ether-ester) blockcopolymers with poly(butylene terephthalate)(PBT) as one of the block segment. A seriesof PBT poly(ether ester) triblock and multiblock copolymers with various molecularweight were synthesized by solution and melting ring-opening polymerization (ROP) ofcyclic oligo(butylene terephthalate)s (COBTs), using dihydroxyl end-functionizedpolyethers as macroinitiator, including poly(ethylene glycol)(PEG), poly(tetramethyleneoxide)(PTMO) and poly(dimethyl siloxane)(PDMS). The structure of the multiblockcopolymers is well characterized by nuclear magnetic resonance (NMR) techniques,together with gel permeation chromatography (GPC), and matrix-assisted laser desorptionionization time-of-flight (MALDI-TOF) measurements. The behaviors of these multiblockcopolymers were measured by differential scanning calorimetry (DSC), thermogravimetricanalysis (TGA), wide-angle X-ray diffraction (WAXD), etc.
The main contents are summarized as follows:
(1) We demonstrated a facile synthesis method to novel double crystalline triblockcopolymers for confinement effect studies. Three PBT-b-PEO-b-PBT triblock copolymerswith same PEO but different PBT molecular weights were synthesized by solution ROP ofCOBTs using PEG as macroinitiator and titanium isopropyloxide as catalyst. The structureof copolymers was well characterized by1H NMR and GPC. TGA results revealed that thedecomposition temperature of PEO in triblock copolymers increased about30°C to thesame as PBT copolymers, after being end-capped with PBT polymers. These triblockcopolymers showed double crystalline properties from PBT and PEO blocks, observedfrom DSC and WAXD measurements. The crystallization of PBT blocks showed thestrong confinement effects on PEO blocks due to covalent linkage of PBT blocks withPEO blocks, where the melting and crystallization temperatures and enthalpiescorresponding to PEO blocks decreased significantly with increment of PBT content. Thecrystal morphology was observed by polarized optical microscopy (POM), andamorphous-like spherulites were observed during PBT crystallization.
(2) The isothermal crystallization kineties and melting behaviors after isothermalcrystallization of PBT homopolymer and PBT-b-PEO-b-PBT triblock copolymers wereinvestigated by DSC. The equilibrium melting temperatures of PBT homopolymer andtriblock copolymers were determined by Hoffman-Weeks equation. The deduced Avramiexponent n varies in the range of3.0~4.0, from the analysis of the crystallization kineticdata using the Avrami equation, indicated that the addition of PEO did not alter the crystalgrowth mechanism. The crystallization rates of the PBT-b-PEO-b-PBT triblockcopolymers were decreased with increasing content of PEO.
(3)(PBT-b-PEO-b-PBT)xmultiblock copolymers was were synthesized by the one potmelt polymerization of COBTs using dihydroxyl end group of PEG-1k as themacroinitiator. NMR techniques including1D-quantitative1H NMR、HSQC and1H-1HCOSY have been used to characterize the multiblock copolymer structures This wasfurther confirmed by MALDI-TOF. An improved quantitative1H NMR technique wasapplied to calculate the absolute molecular weights by the chain end and functional groupsestimation. It was found that the polymerization efficiency decreased when the molecularweight of PEO increased to4,000or10,000Da.
(4) A novel method is utilized to synthesize (PBT-b-PTMO-b-PBT)xmultiblockcopolymers by the one pot melt polymerization of COBTs using PTMO as a macroinitiator.The NMR techniques (1D-quantitative1H NMR and1H-1H COSY) have been used tocharacterize and reveal the multiblock copolymer structures and absolute molecularweights. It was found the molecular weights of the multiblock copolymers increasedlinearly with reaction time. The structures of the multiblock copolymers are furthercharacterized by GPC. The polymerization kinetics is slightly affected and incresed withthe catalyst content. These multiblock copolymers show improved thermal stability whencompared to PTMO homopolymers. The mechanical properties test at room temperatureindicates the elongation of the multiblock copolymers increased with molecular weights.
(5) A series of PBT-PDMS multiblock copolymer with different mass content ofPDMS were synthesized by using dihydroxyl end functioned group ofpoly(dimethylsiloxane) as macroinitiator, and their properties are measured.1H NMR andGPC analysis reveals the formation of block copolymers, with very low polymerizationefficiency and unknown block copolymer structure.
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