基于超支化聚缩水甘油醚的复杂结构星型聚合物的合成研究
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摘要
具有复杂结构的共聚物的设计与合成是目前高分子合成研究中的热点之一。由于活性聚合技术的发展,特别是通过活性自由基聚合与离子型聚合相结合,人们设计合成出了各种线形和非线形结构(梳型、星形、树枝状、超支化等)的共聚物。这些共聚物结构的特殊性使其能形成丰富的自组装形态,并且在化学,物理,生物等领域中有着广泛的潜在的用途。目前对于三维梳型接枝共聚物的研究,特别是对其后续的性质、结构、形态的研究非常有限,主要是由于其在合成上还存在着很大的困难。这主要归结于单一的聚合技术应用的局限和分子设计的缺陷。但是其特殊的结构具有的独特性能又是非常诱人的,所以探索新的方法合成三维梳型接枝共聚物将是一项非常重要的工作。
本文把“活性”阴离子聚合、原子转移自由基聚合(ATRP)和可逆加成—裂解链转移(RAFT)反应结合起来,利用聚合物端基官能团之间的转换和偶合反应(原子转移氮氧自由基偶合反应(ATNRC)和“Click”化学反应),设计、合成了一系列星型嵌段和星型混合接枝共聚物。我们所取得的主要结果如下:
1.用1,1,1-三羟甲基丙烷(TMP)和甲醇钾组成的阴离子引发剂体系使缩水甘油(glycerol)聚合,得到结构明确超支化聚缩水甘油醚(HPG)。通过改变投入的酰化试剂2-溴异丁酰溴的量,得到了HPG表面羟基不同溴化程度的,适合于ATRP聚合的大分子引发剂HPG-g-Br。利用这种大分子引发剂通过ATRP聚合技术引发苯乙烯(St)单体聚合得到星型接枝共聚物HPG-g-PS。继续投入丙烯酸叔丁酯(tBA)单体进行ATRP聚合,得到星型嵌段接枝共聚物HPG-g-(PS-b-PtBA)。对PtBA链段进行选择性水解,得到星型嵌段接枝共聚物HPG-g-(PS-b-PAA)。通过水解位于HPG和PS链之间的酯键测定PS-b-PAA的分子量和组成,并通过计算精确得到了HPG-g-(PS-b-PtBA(PAA))的分子量。实验证明,通过适当的断裂侧链,我们可以精确计算结构复杂的星型嵌段接枝共聚物的分子量和组成。
2.将HPG-g-PS上剩余的OH与S-1-十二烷基-S'-(α,α'-二甲基-α”-乙酸基)三硫酯进行酯化反应,得到有很多三硫酯基,适用于RAFT聚合的大分子链转移剂HPG-g-PS/DDAT。利用这种大分子链转移剂调控丙烯酸叔丁酯(tBA)单体的RAFT聚合,得到星型混合接枝共聚物HPG-g-PS/PtBA。对PtBA链段进行选择性水解,得到星型混合接枝共聚物HPG-g-PS/PAA。通过水解位于HPG和PS或PAA之间的酯键测定PAA的分子量,并通过计算精确得到HPG-g-PS/PtBA(PAA)的分子量。实验证明,在我们的实验环境下,ATRP聚合残余的Br原子不会对RAFT聚合产生影响。但是我们发现,接枝链的数目和分子量对聚合物的结构有相当大的影响。当每个聚合物分子上PS链的数目低于66,分子量小于1,800 Da时,93%的DDAT可以参与RAFT的调控。
3.设计合成了带有TEMPO基团的小分子化合物:4-羟基-2,2,6,6-四甲基哌啶氮氧自由基(HTEMPO)。在二苯基甲基钾(DPMK)和HTEMPO组成的阴离子引发体系作用下,使环氧乙烷(EO)聚合,得到端基带有TEMPO基团的聚环氧乙烷(PEO)。将TEMPO-PEO和HPG-g-PS在溴化亚铜(CuBr)和1,1,4,7,7-五甲基二乙基三胺(PMDETA)的催化下,进行原子转移氮氧自由基偶合反应(ATNRC)最终得到星型嵌段接枝共聚物HPG-g-(PS-b-PEO)。通过水解位于HPG和PS链之间的酯键测定PS-b-PEO和HPG-g-(PS-b-PEO)的分子量和组成。实验发现,在PS链的密度非常大的时候(210),ATNRC的反应效率仍然非常高(92%)。
4.选择1-乙氧基乙基-2,3-环氧丙醚(EEGE)作为小分子“盖帽”试剂,对“活性”苯乙烯阴离子进行封端反应,得到的聚苯乙烯在ω端含有一个“活性”羟基和一个1-乙氧基乙基保护的羟基(PS-EEGE)。在此基础上,通过一系列修饰,制备得到端基同时含炔基和溴原子的大分子引发剂,以此引发丙烯酸叔丁酯通过ATRP反应得到嵌段聚合物PS-b-PtBA,在该聚合物的链段连接处含有一个炔基官能团。同时,将HPG外围的羟基进行叠氮化。在CuBr和PMDETA的存在下,使链段中间分别含有炔基的嵌段聚合物PS-b-PtBA和叠氮基团的HPG-g-N_3进行“Click”化学反应,得到侧链PS和PtBA数目为1:1的星型混合接枝共聚物HPG-g-PS/PtBA。
Design and synthesis of copolymer with complex architecture are always pursued by polymer chemists in past decades.Thanks to the development of controlled polymerization,some linear and nonlinear(such as comb-like,star, dendritic,hyperbranched) copolymers are synthesized by means of the combination of the controlled radical polymerization with ionic polymerization,.These special architectural copolymers may form abundant morphologies in selective solvent or in bulk and have potential applications in chemistry,physics and biology.Up till now, the publications on three-dimensional graft polymer brushes are so limited because of the difficulty in synthesis.It may attribute to the limitation of single polymerization methodology and defects in molecular design.However,it is a very exciting work to prepare this kind of special copolymers with unique properties,thus it is an important to explore a novel synthesis strategy for these copolymers with complicated three-dimensional structures.
In this thesis,the sythesis and characterization of blocked-arm star polymers and mixed-arm star polymers are performed by the combination of "Controlled/Living" Polymerization(ATRP and RAFT) and the coupling reaction("Click" Reaction and ATNRC) is also used in the preparation process.Our work provided a universal method for the synthesis of three-dimensional graft polymer brushes with complicated structure.The essential results obtained are shown as follows:
1.The well-defined hyperbranched polyglycerol(HPG) was prepared by anionic polymerization of glycerol using 1,1,1-trihydroxymethyl propane and methanol potassium as initiation system.After esterified with 2-bromoisobutyryl bromide by different proportion,the macroinitiator HPG-g-Br with 2-bromoisobutyryl groups in its periphery initiated the ATRP of styrene(St) to obtain star polymer HPG-g-PS.The star polymers with HPG core and PS-b-PtBA or PS-b-PAA block copolymer side chains could be successfully synthesized by sequential ATRP.In the whole preparation,no homopolymers of PS and PtBA were detected,and so the purification procedure was very simple.By detachment of PS and PS-b-PAA side chains from the HPG core,the reliable molecular weight of star polymers could be obtained.
2.The remaining hydroxyl groups of HPG-g-PS could be further reacted with chain transfer agent S-1-dodecyl-S'-(α,α'-dimethyl-α"-acetic acid) trithiocarbonate (DDAT) to obtain HPG-g-PS/DDAT,then the mixed-arm star polymers, HPG-g-PS/PtBA and HPG-g-PS/PAA were successfully synthesized by sequential RAFT.It was found that the arm length and arm number exert great effect on the structure of star polymers with mixed-arms.The initiation efficiency of the DDAT in the core of star molecules was evaluated by the linear polymers formed by the cleavage of the ester bond between the core and the mixed-arm in the presence of sodium hydroxide.It was found only if the arm number of PS was less than 66 and the molecular weight of PS was lower than 1,800 Da,then high initiation efficiency(93%) of DDAT could be reached.
3.A heterofunctional initiatiation system composed of 4-hydoxyl-2,2,6, 6-tetramethyl piperidyl-1-oxyl(HTEMPO) and diphenylmethyl potassium(DPMK) were used to initiate the polymerization of ethylene oxide to produce TEMPO-PEO. The latter was reacted with HPG-g-PS in the presence of CuBr and PMDETA to produce blocked-arm star polymer HPG-g-(PS-b-PEO) by atom transfer nitroxide radical coupling(ATNRC) reaction.The efficiency of the coupling reaction could reach 92%even there were 210 PS chains on one HPG core.
4.The poly(styryl)lithium was capped by ethoxyethyl glycidyl ether(EEGE) to form the functionalized PS-EEGE with an activeω-hydroxyl group and anω'-ethoxyethyl-protected hydroxyl group.The alkyne group and bromide atom were introduced onto PS end by a series of modification of the functional group.The obtained polymer was used as the macroinitiator and the diblock copolymer PS-b-PtBA with an alkyne group at the junction point was obtained by the ATRP of tert-butylacrylate(tBA).HPG-g-N_3 was produced by azidation of HPG-g-Br.Finally, the "Click" reaction was preceded between the azide group and alkyne group using CuBr and PMDETA as catalyst.Thus,the mixed-arm star polymers HPG-g-PS/PtBA with identical PS and PtBA side chains was obtained.
本文把“活性”阴离子聚合、原子转移自由基聚合(ATRP)和可逆加成—裂解链转移(RAFT)反应结合起来,利用聚合物端基官能团之间的转换和偶合反应(原子转移氮氧自由基偶合反应(ATNRC)和“Click”化学反应),设计、合成了一系列星型嵌段和星型混合接枝共聚物。我们所取得的主要结果如下:
1.用1,1,1-三羟甲基丙烷(TMP)和甲醇钾组成的阴离子引发剂体系使缩水甘油(glycerol)聚合,得到结构明确超支化聚缩水甘油醚(HPG)。通过改变投入的酰化试剂2-溴异丁酰溴的量,得到了HPG表面羟基不同溴化程度的,适合于ATRP聚合的大分子引发剂HPG-g-Br。利用这种大分子引发剂通过ATRP聚合技术引发苯乙烯(St)单体聚合得到星型接枝共聚物HPG-g-PS。继续投入丙烯酸叔丁酯(tBA)单体进行ATRP聚合,得到星型嵌段接枝共聚物HPG-g-(PS-b-PtBA)。对PtBA链段进行选择性水解,得到星型嵌段接枝共聚物HPG-g-(PS-b-PAA)。通过水解位于HPG和PS链之间的酯键测定PS-b-PAA的分子量和组成,并通过计算精确得到了HPG-g-(PS-b-PtBA(PAA))的分子量。实验证明,通过适当的断裂侧链,我们可以精确计算结构复杂的星型嵌段接枝共聚物的分子量和组成。
2.将HPG-g-PS上剩余的OH与S-1-十二烷基-S'-(α,α'-二甲基-α”-乙酸基)三硫酯进行酯化反应,得到有很多三硫酯基,适用于RAFT聚合的大分子链转移剂HPG-g-PS/DDAT。利用这种大分子链转移剂调控丙烯酸叔丁酯(tBA)单体的RAFT聚合,得到星型混合接枝共聚物HPG-g-PS/PtBA。对PtBA链段进行选择性水解,得到星型混合接枝共聚物HPG-g-PS/PAA。通过水解位于HPG和PS或PAA之间的酯键测定PAA的分子量,并通过计算精确得到HPG-g-PS/PtBA(PAA)的分子量。实验证明,在我们的实验环境下,ATRP聚合残余的Br原子不会对RAFT聚合产生影响。但是我们发现,接枝链的数目和分子量对聚合物的结构有相当大的影响。当每个聚合物分子上PS链的数目低于66,分子量小于1,800 Da时,93%的DDAT可以参与RAFT的调控。
3.设计合成了带有TEMPO基团的小分子化合物:4-羟基-2,2,6,6-四甲基哌啶氮氧自由基(HTEMPO)。在二苯基甲基钾(DPMK)和HTEMPO组成的阴离子引发体系作用下,使环氧乙烷(EO)聚合,得到端基带有TEMPO基团的聚环氧乙烷(PEO)。将TEMPO-PEO和HPG-g-PS在溴化亚铜(CuBr)和1,1,4,7,7-五甲基二乙基三胺(PMDETA)的催化下,进行原子转移氮氧自由基偶合反应(ATNRC)最终得到星型嵌段接枝共聚物HPG-g-(PS-b-PEO)。通过水解位于HPG和PS链之间的酯键测定PS-b-PEO和HPG-g-(PS-b-PEO)的分子量和组成。实验发现,在PS链的密度非常大的时候(210),ATNRC的反应效率仍然非常高(92%)。
4.选择1-乙氧基乙基-2,3-环氧丙醚(EEGE)作为小分子“盖帽”试剂,对“活性”苯乙烯阴离子进行封端反应,得到的聚苯乙烯在ω端含有一个“活性”羟基和一个1-乙氧基乙基保护的羟基(PS-EEGE)。在此基础上,通过一系列修饰,制备得到端基同时含炔基和溴原子的大分子引发剂,以此引发丙烯酸叔丁酯通过ATRP反应得到嵌段聚合物PS-b-PtBA,在该聚合物的链段连接处含有一个炔基官能团。同时,将HPG外围的羟基进行叠氮化。在CuBr和PMDETA的存在下,使链段中间分别含有炔基的嵌段聚合物PS-b-PtBA和叠氮基团的HPG-g-N_3进行“Click”化学反应,得到侧链PS和PtBA数目为1:1的星型混合接枝共聚物HPG-g-PS/PtBA。
Design and synthesis of copolymer with complex architecture are always pursued by polymer chemists in past decades.Thanks to the development of controlled polymerization,some linear and nonlinear(such as comb-like,star, dendritic,hyperbranched) copolymers are synthesized by means of the combination of the controlled radical polymerization with ionic polymerization,.These special architectural copolymers may form abundant morphologies in selective solvent or in bulk and have potential applications in chemistry,physics and biology.Up till now, the publications on three-dimensional graft polymer brushes are so limited because of the difficulty in synthesis.It may attribute to the limitation of single polymerization methodology and defects in molecular design.However,it is a very exciting work to prepare this kind of special copolymers with unique properties,thus it is an important to explore a novel synthesis strategy for these copolymers with complicated three-dimensional structures.
In this thesis,the sythesis and characterization of blocked-arm star polymers and mixed-arm star polymers are performed by the combination of "Controlled/Living" Polymerization(ATRP and RAFT) and the coupling reaction("Click" Reaction and ATNRC) is also used in the preparation process.Our work provided a universal method for the synthesis of three-dimensional graft polymer brushes with complicated structure.The essential results obtained are shown as follows:
1.The well-defined hyperbranched polyglycerol(HPG) was prepared by anionic polymerization of glycerol using 1,1,1-trihydroxymethyl propane and methanol potassium as initiation system.After esterified with 2-bromoisobutyryl bromide by different proportion,the macroinitiator HPG-g-Br with 2-bromoisobutyryl groups in its periphery initiated the ATRP of styrene(St) to obtain star polymer HPG-g-PS.The star polymers with HPG core and PS-b-PtBA or PS-b-PAA block copolymer side chains could be successfully synthesized by sequential ATRP.In the whole preparation,no homopolymers of PS and PtBA were detected,and so the purification procedure was very simple.By detachment of PS and PS-b-PAA side chains from the HPG core,the reliable molecular weight of star polymers could be obtained.
2.The remaining hydroxyl groups of HPG-g-PS could be further reacted with chain transfer agent S-1-dodecyl-S'-(α,α'-dimethyl-α"-acetic acid) trithiocarbonate (DDAT) to obtain HPG-g-PS/DDAT,then the mixed-arm star polymers, HPG-g-PS/PtBA and HPG-g-PS/PAA were successfully synthesized by sequential RAFT.It was found that the arm length and arm number exert great effect on the structure of star polymers with mixed-arms.The initiation efficiency of the DDAT in the core of star molecules was evaluated by the linear polymers formed by the cleavage of the ester bond between the core and the mixed-arm in the presence of sodium hydroxide.It was found only if the arm number of PS was less than 66 and the molecular weight of PS was lower than 1,800 Da,then high initiation efficiency(93%) of DDAT could be reached.
3.A heterofunctional initiatiation system composed of 4-hydoxyl-2,2,6, 6-tetramethyl piperidyl-1-oxyl(HTEMPO) and diphenylmethyl potassium(DPMK) were used to initiate the polymerization of ethylene oxide to produce TEMPO-PEO. The latter was reacted with HPG-g-PS in the presence of CuBr and PMDETA to produce blocked-arm star polymer HPG-g-(PS-b-PEO) by atom transfer nitroxide radical coupling(ATNRC) reaction.The efficiency of the coupling reaction could reach 92%even there were 210 PS chains on one HPG core.
4.The poly(styryl)lithium was capped by ethoxyethyl glycidyl ether(EEGE) to form the functionalized PS-EEGE with an activeω-hydroxyl group and anω'-ethoxyethyl-protected hydroxyl group.The alkyne group and bromide atom were introduced onto PS end by a series of modification of the functional group.The obtained polymer was used as the macroinitiator and the diblock copolymer PS-b-PtBA with an alkyne group at the junction point was obtained by the ATRP of tert-butylacrylate(tBA).HPG-g-N_3 was produced by azidation of HPG-g-Br.Finally, the "Click" reaction was preceded between the azide group and alkyne group using CuBr and PMDETA as catalyst.Thus,the mixed-arm star polymers HPG-g-PS/PtBA with identical PS and PtBA side chains was obtained.
引文
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