醋酸乙烯酯可逆加成断裂链转移自由基聚合
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摘要
醋酸乙烯酯(Vinyl acetate,VAc)是一种工业上广泛应用的非共轭乙烯基单体,可以采用黄原酸酯为RAFT试剂、利用可逆加成断裂链转移(RAFT)机理进行该单体的“活性”/可控自由基聚合,从而可以通过进料控制策略实现聚合物链组成与序列结构的控制,制备具有特定链结构的聚醋酸乙烯酯均聚物和共聚物。VAc的自由基异常活泼,在聚合中容易发生向聚合物的链转移反应,实现VAc的“活性”/可控自由基聚合是一个挑战。
研究与开发VAc RAFT聚合过程要解决两个核心问题:一是聚合的动力学特征,即聚合的快慢(过程)与多少(平衡);二是聚合物的分子特征,即数均分子量的大小、分子量分布以及聚合过程中数均分子量随转化率是否具有线性增长关系的“活性”特征。
针对聚合的动力学特征和聚合物的分子特征,本文就黄原酸酯RAFT试剂结构、RAFT试剂与引发剂的比例[RAFT]/[I]、引发剂的类型与浓度、溶液及细乳液的聚合实施方法,以及反应型助稳定剂对VAc RAFT聚合的影响与作用展开研究,得到了如下结论.
在乙酸乙酯溶剂体系中考察了RAFT试剂结构、[RAFT]/[I]、单体浓度对VAcRAFT溶液聚合规律的影响。发现RAFT试剂Z基团的吸电子能力对聚合动力学和链可控性有显著影响,Z基团具有较强吸电子能力的MPhSA和CPDB在溶液、本体和细乳液体系中的聚合均导致缓聚和阻聚,而Z基团具有一定推电子能力的MMSA、MESA、MiPSA均可以有效的调控VAc进行RAFT聚合。聚合物的数均分子量随转化率线性增加,分子量分布指数在1.2～1.6之间,具有良好的链可控性。
考察并比较了MMSA为RAFT试剂的VAc RAFT溶液聚合和细乳液聚合的聚合动力学特征与聚合物分子特征,研究表明两者均有较好的“活性”/可控聚合特征。与溶液聚合相比,细乳液聚合具有诱导期短、增长速率快、最终聚合转化率高、聚合物数均分子量高,同时聚合在水介质中进行,环境友好、能耗低,是VAc RAFT聚合工业实施的理想体系,但分子量分布较溶液聚合产物略宽。不同聚合体系中虽然程度不同,但是链自由基的终止和链自由基向聚合物链转移是造成可控性下降的主要原因。
系统研究了RAFT试剂结构、引发剂类型、[RAFT]/[I]、乳化剂类型对VAcRAFT细乳液聚合规律的影响。发现在细乳液体系中MMSA、MESA、MiPSA同样可以较好的调控VAc RAFT聚合;水溶性引发剂引发的聚合诱导期短、聚合速率快、最终转化率高。随着[RAFT]/[I]的增加,聚合阻聚和缓聚程度增加。以V44为引发剂的聚合体系诱导期最短、聚合速率最快、最终转化率最高,这与水溶性引发剂的引发效率高、阴离子型乳化剂SDS稳定的单体液滴有利于捕获V44自由基有关。
研究并制备了窄分子量分布的α-乙烯基聚有机氟硅氧烷(分子量分布指数小于1.1),并以其替代十六烷作为细乳液聚合的助稳定剂,考察了此类反应型助稳定剂对VAc RAFT细乳液聚合规律的影响。发现采用SDS/OP10的复合乳化剂体系时,VAc的RAFT聚合可控性较好,但是乳胶粒径呈多峰分布;由于α-乙烯基聚有机氟硅氧烷与VAc共聚活性低,造成了采用α-乙烯基聚有机氟硅氧烷为助稳定剂的细乳液聚合中长期存在一些没有成核的单体液滴,在聚合温度下这些单体液滴容易聚并,造成了细乳液乳胶粒径呈多峰分布。
本文初步研究了VAc RAFT聚合中聚合动力学特征和聚合物链结构特征,所得结论为VAc RAFT聚合的实际应用提供了依据。
As a kind of non-conjugated monomer with wide industrial applications,the RAFT polymerization of vinyl acetate mediated by xanthate proceeds in controlled way.Through feeding strategy,the composite and sequence structure of polymer can be controlled and PVAc homopolymer and copolymer with special structure can be prepared.Because of very high reactivity of the vinyl acetate propagating radical, chain transfer and termination often take place in polymerization of VAc.So,it is a big challenge to realize "living"/controlled free radical polymerization of VAc.
During RAFT polymerization of vinyl acetate,tow problems should be solved: dynamic characterizations,i.e.polymerization rate and final conversion of VAc,the other one is chain structure characterizations,i.e.average molecular weight, molecular weight distribution and "living" nature:if Mn of polymer increases linearly with conversion.
This paper focuses on the tow problems during RAFT polymerization of VAc. The effects of RAFT agents,ratio of RAFT to initiator,type of initiator, polymerization systems and reactive costabilizer on RAFT polymerization of VAc were carried out.
The reversible addition fragmentation chain transfer radical polymerization of vinyl acetate(VAc) was carried out in ethyl acetate.The effects of RAFT agents,ratio of RAFT to initiator and monomer concentration were studied.The draw electricity ability of Z group in RAFT agent has prominent effect on dynamics and controlling characterization of chain.In the presence of MPhSA and CPDB with strong drawing electricity ability of Z groups,RAFT polymerization of VAc showed inhibition and retardation.In the presence of MMSA,MESA and MiPSA with repelling electricity ability of Z groups,the RAFT radical polymerization of VAc could proceed in a "living"/controlled way,the number-average molecular weight of PVAc increased linearly with the conversion,the PDI is 1.2～1.6.
The RAFT polymerizations of VAc mediated by MMSA in solution and miniemulsion were carried out.All polymerizations of VAc preceeded in controlled way.Compared with solution polymerizations,the induction period in RAFT miniemulsion polymerization initiated by KPS was the shortest,propagation coefficient was the highest and molecular weight was the highest.At the same time, miniemulsion is an environmentally friendly system to carry out RAFT polymerization of VAc.The PDI of polymer obtained from miniemulsion was higher than that in solution polymerization.Losing activity of RAFT agent and chain transfer to polymer were responsible for losing control of polymerization.
The effects of xanthate,the type of initiator,the ratio of xanthate to initiator and the type of emulsifier on RAFT miniemulsion polymerization of VAc were investigated.The polymerization of VAc mediated by MMSA,MESA,MiPSA could proceed in controlled way.The polymerization initiated by water-soluble initiator showed shortest inhibition period,fastest rate and highest conversion than other initiators.With increasing of RAFT agent,inhibition and retardation of polymerization are increasing.Initialed by V44,the polymerizations showed shortest inhibition period,fastest rate and highest conversion.
Instead of HD withα-vinyl organosiloxane polymer as costabilizer,the RAFT miniemulsion of VAc was carried out.Multiple peaks were observed in the latex particle size distribution stabilized by SDS/OP10 emulsifier system,the polymerization of VAc preceded in controlled way.Through qualitative analysis by ~1H-NMR,the reason of multiple peaks in latex particle size distribution was coalescent of droplet under polymerization temperature.
Dynamic and chain structure characterizations in RAFT polymerization of VAc was studied and conclusions were in favor of realizing application of VAc RAFT polymerization.
研究与开发VAc RAFT聚合过程要解决两个核心问题:一是聚合的动力学特征,即聚合的快慢(过程)与多少(平衡);二是聚合物的分子特征,即数均分子量的大小、分子量分布以及聚合过程中数均分子量随转化率是否具有线性增长关系的“活性”特征。
针对聚合的动力学特征和聚合物的分子特征,本文就黄原酸酯RAFT试剂结构、RAFT试剂与引发剂的比例[RAFT]/[I]、引发剂的类型与浓度、溶液及细乳液的聚合实施方法,以及反应型助稳定剂对VAc RAFT聚合的影响与作用展开研究,得到了如下结论.
在乙酸乙酯溶剂体系中考察了RAFT试剂结构、[RAFT]/[I]、单体浓度对VAcRAFT溶液聚合规律的影响。发现RAFT试剂Z基团的吸电子能力对聚合动力学和链可控性有显著影响,Z基团具有较强吸电子能力的MPhSA和CPDB在溶液、本体和细乳液体系中的聚合均导致缓聚和阻聚,而Z基团具有一定推电子能力的MMSA、MESA、MiPSA均可以有效的调控VAc进行RAFT聚合。聚合物的数均分子量随转化率线性增加,分子量分布指数在1.2～1.6之间,具有良好的链可控性。
考察并比较了MMSA为RAFT试剂的VAc RAFT溶液聚合和细乳液聚合的聚合动力学特征与聚合物分子特征,研究表明两者均有较好的“活性”/可控聚合特征。与溶液聚合相比,细乳液聚合具有诱导期短、增长速率快、最终聚合转化率高、聚合物数均分子量高,同时聚合在水介质中进行,环境友好、能耗低,是VAc RAFT聚合工业实施的理想体系,但分子量分布较溶液聚合产物略宽。不同聚合体系中虽然程度不同,但是链自由基的终止和链自由基向聚合物链转移是造成可控性下降的主要原因。
系统研究了RAFT试剂结构、引发剂类型、[RAFT]/[I]、乳化剂类型对VAcRAFT细乳液聚合规律的影响。发现在细乳液体系中MMSA、MESA、MiPSA同样可以较好的调控VAc RAFT聚合;水溶性引发剂引发的聚合诱导期短、聚合速率快、最终转化率高。随着[RAFT]/[I]的增加,聚合阻聚和缓聚程度增加。以V44为引发剂的聚合体系诱导期最短、聚合速率最快、最终转化率最高,这与水溶性引发剂的引发效率高、阴离子型乳化剂SDS稳定的单体液滴有利于捕获V44自由基有关。
研究并制备了窄分子量分布的α-乙烯基聚有机氟硅氧烷(分子量分布指数小于1.1),并以其替代十六烷作为细乳液聚合的助稳定剂,考察了此类反应型助稳定剂对VAc RAFT细乳液聚合规律的影响。发现采用SDS/OP10的复合乳化剂体系时,VAc的RAFT聚合可控性较好,但是乳胶粒径呈多峰分布;由于α-乙烯基聚有机氟硅氧烷与VAc共聚活性低,造成了采用α-乙烯基聚有机氟硅氧烷为助稳定剂的细乳液聚合中长期存在一些没有成核的单体液滴,在聚合温度下这些单体液滴容易聚并,造成了细乳液乳胶粒径呈多峰分布。
本文初步研究了VAc RAFT聚合中聚合动力学特征和聚合物链结构特征,所得结论为VAc RAFT聚合的实际应用提供了依据。
As a kind of non-conjugated monomer with wide industrial applications,the RAFT polymerization of vinyl acetate mediated by xanthate proceeds in controlled way.Through feeding strategy,the composite and sequence structure of polymer can be controlled and PVAc homopolymer and copolymer with special structure can be prepared.Because of very high reactivity of the vinyl acetate propagating radical, chain transfer and termination often take place in polymerization of VAc.So,it is a big challenge to realize "living"/controlled free radical polymerization of VAc.
During RAFT polymerization of vinyl acetate,tow problems should be solved: dynamic characterizations,i.e.polymerization rate and final conversion of VAc,the other one is chain structure characterizations,i.e.average molecular weight, molecular weight distribution and "living" nature:if Mn of polymer increases linearly with conversion.
This paper focuses on the tow problems during RAFT polymerization of VAc. The effects of RAFT agents,ratio of RAFT to initiator,type of initiator, polymerization systems and reactive costabilizer on RAFT polymerization of VAc were carried out.
The reversible addition fragmentation chain transfer radical polymerization of vinyl acetate(VAc) was carried out in ethyl acetate.The effects of RAFT agents,ratio of RAFT to initiator and monomer concentration were studied.The draw electricity ability of Z group in RAFT agent has prominent effect on dynamics and controlling characterization of chain.In the presence of MPhSA and CPDB with strong drawing electricity ability of Z groups,RAFT polymerization of VAc showed inhibition and retardation.In the presence of MMSA,MESA and MiPSA with repelling electricity ability of Z groups,the RAFT radical polymerization of VAc could proceed in a "living"/controlled way,the number-average molecular weight of PVAc increased linearly with the conversion,the PDI is 1.2～1.6.
The RAFT polymerizations of VAc mediated by MMSA in solution and miniemulsion were carried out.All polymerizations of VAc preceeded in controlled way.Compared with solution polymerizations,the induction period in RAFT miniemulsion polymerization initiated by KPS was the shortest,propagation coefficient was the highest and molecular weight was the highest.At the same time, miniemulsion is an environmentally friendly system to carry out RAFT polymerization of VAc.The PDI of polymer obtained from miniemulsion was higher than that in solution polymerization.Losing activity of RAFT agent and chain transfer to polymer were responsible for losing control of polymerization.
The effects of xanthate,the type of initiator,the ratio of xanthate to initiator and the type of emulsifier on RAFT miniemulsion polymerization of VAc were investigated.The polymerization of VAc mediated by MMSA,MESA,MiPSA could proceed in controlled way.The polymerization initiated by water-soluble initiator showed shortest inhibition period,fastest rate and highest conversion than other initiators.With increasing of RAFT agent,inhibition and retardation of polymerization are increasing.Initialed by V44,the polymerizations showed shortest inhibition period,fastest rate and highest conversion.
Instead of HD withα-vinyl organosiloxane polymer as costabilizer,the RAFT miniemulsion of VAc was carried out.Multiple peaks were observed in the latex particle size distribution stabilized by SDS/OP10 emulsifier system,the polymerization of VAc preceded in controlled way.Through qualitative analysis by ~1H-NMR,the reason of multiple peaks in latex particle size distribution was coalescent of droplet under polymerization temperature.
Dynamic and chain structure characterizations in RAFT polymerization of VAc was studied and conclusions were in favor of realizing application of VAc RAFT polymerization.
引文
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