接枝共聚物的可控合成、溶液性质及其应用基础研究
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摘要
两亲聚合物分子中同时具有分别对两种不同相结构(如水相与油相、两种油相、两种不相容的固相等)具有亲和性的链段,一般而言指同时具有亲油性和亲水性的高聚物。由于两亲聚合物在结构上的特点(亲油部分和亲水部分不相容而易发生微相分离),使得两亲聚合物在选择性溶剂、表面和本体结构中呈现出独特的性质,应用广泛。其中接枝聚合物由于拥有线型聚合物所不曾具有的一些独特性能,受到了研究者的广泛关注。本文通过催化链转移聚合(CCTP)一步合成末端带有可聚合双键的聚丙烯酸酯类大分子单体,然后大分子单体与普通单体共聚制备得到接枝型丙烯酸酯类聚合物。进而对所合成的接枝型两亲聚合物的溶液性质及其与小分子表面活性剂十六烷基三甲基溴化铵(CTAB)、十二烷基硫酸钠(SDS)的相互作用进行了系统研究。同时考察了此类接枝聚合物分别在二甲苯和水体系中的炭黑分散性能与聚合物结构的关系。此外,还通过小分子多胺和大分子单体酯基之间的取代反应制备得到接枝型的聚阳离子,研究其复合质粒DNA的能力、材料毒性以及体外细胞转染的效率。本论文的主要工作如下：
(1)利用CCTP方法设计合成了支链亲水、主链疏水的阴离子型的接枝型两亲聚合物,表面张力研究发现水溶液中该两亲聚合物没有明显的临界胶束浓度(CMC),动态光散射(DLS)与透射电镜(TEM)结果表明很低浓度时体系中即有聚集体形成。同时,研究了两亲聚合物与阳离子表面活性剂CTAB、以及阴离子表面活性剂SDS之间的相互作用。结果表明该阴离子型两亲聚合物与CTAB可形成结构紧密的复合物,复合物的粒径以及Zeta电势与CTAB的浓度有关；两亲聚合物与CTAB之间主要通过阴阳离子的静电引力而发生相互作用。而在两亲聚合物-SDS体系中,研究表明尽管聚合物与SDS之间存在较为强烈的同号电荷之间的静电排斥作用,但是两亲聚合物与SDS仍然可以通过两者疏水结构之间的疏水吸引力而发生相互作用。
(2)采用类似技术路线合成了主链分别含有羧基、胺基以及季铵基的油溶性接枝聚合物,研究了羧基、胺基以及季铵基团对聚合物在二甲苯中分散炭黑能力的影响。结果表明主链中官能团的含量对炭黑的分散有较大的影响；而主链含胺基的接枝聚合物的炭黑分散能力比含羧基的样品好；通过将聚合物主链中的胺基季铵化,可大大提高接枝聚合物对炭黑的分散能力,能达到商业分散剂Disperbyk-163的炭黑分散能力。
(3)设计合成了多种主链疏水、支链亲水的两亲接枝型聚合物,研究了聚合物疏水主链的组成、亲水链和疏水链长度以及官能团含量对该聚合物在水中分散炭黑的影响。结果表明疏水主链含适量的胺基和苯基官能团均对炭黑的分散有利,胺基单体含量为疏水主链单体总量的5%时分散效果最好。此外,聚合物用量、溶液离子强度以及体系pH值对炭黑的分散均有较大的影响,当体系中有电解质存在或者溶液呈现酸性时对炭黑的分散不利。优化的聚合物分散剂所制备的炭黑分散体具有较好的静置稳定性,放置三个月仍能表现出良好的分散状态,其炭黑分散能力与商业分散剂Disperbyk-190相当。
(4)通过小分子多胺与大分子单体PMMA酯基之间的氨解反应制备了丙烯酸酯类聚阳离子(PMMA-g-oligoamines),通过琼脂糖凝胶电泳、TEM、DLS、Zeta电势研究了聚阳离子对质粒DNA的复合能力。结果表明三种聚阳离子均可以有效的和DNA形成结构紧密的复合物,复合物粒径在200nm左右,电位值则达到了20mV以上。细胞毒性结果表明三种聚阳离子对HEK293T和HeLa细胞的细胞毒性远远低于25 kDa PEI的毒性(25 kDa PEI的毒性为合成的聚阳离子毒性的100多倍)。对细胞的体外转染结果表明三种聚阳离子均可以把质粒DNA有效地转入HEK293T和HeLa细胞中,且在两种细胞中的转染效率达到了25 kDa PEI的转染效率。此外,激光共聚焦结果表明三种聚阳离子均可以有效的把质粒DNA转入到细胞核中。
Amphiphilic polymers have attracted much attention in the past because of their special aggregating behavior in bulk, selected solvents and surfaces. Normally, there are two different kinds of polymeric chains co-existed in amphiphilic polymer structures, which show different affinity to the two different phases (e.g. water and oil, two kinds of oils or solids with different characters). In this thesis, we focused on graft acrylic polymers (one of the widely industrial utilized amphiphilic polymers), which were copolymerized by CCTP (catalytic chain transfer polymerization)-synthesized macromonomer and nomal acrylic monomers. Moreover, the solution behavior of amphiphilic graft polymers and the influence of small surfactants (Cetyltrimethylammonium bromide (CTAB), or Sodium dodecyl sulfate (SDS)) have also been studied systematically. And the graft polymers with proper structures were applicated as dispersants to stabilize carbon black (CB) particles in xylene or water. Besides, graft polycations were synthesized via the aminolysis reaction between oligoamines and CCTP macromonomer; and the cytotoxicity, ability for complexeing with plasmid DNA and efficiency for in vitro transfection of the polycations were evaluated.
(1) The anionic amphiphilic graft polymer (the main chain is hydrophobic and the side chain is hydrophilic) was prepared via CCTP method. Surface tension study indicates that the amphiphilic graft polymer has no evident critical micelle concentration (CMC). Dynamic light scattering (DLS) and transmission electron microscope (TEM) results reveal that even at extremely low concentration, there are aggregates existed in the amphiphilic polymer solution. In addition, the interactions between the anionic polymer and cationic surfactant CTAB and anionic surfactant SDS were studied. The data shown that the anionic amphiphilic polymer could interact with CTAB forming compact complexes; the size and Zeta potential of the complexes was dependent on the CTAB concentration. The interaction between the polymer and CTAB is mainly anionic-cationic electrostatic attractions. In the system of amphiphilic polymer/SDS, the studies revealed that although strong electrostatic repulsions were existed between both of them, the amphiphilic polymer could still interact with SDS by hydrophobic attractions which are originated from the hydrophobic chains of the polymer and SDS.
(2) Three kinds of oil-soluble graft polymers (containing carboxylic, amino and quaternary ammonium groups in the main chain respectively) were synthesized via the similar synthetic route, and the influences of the functional groups on the abilities of the polymers to disperse CB in xylene were evaluated. The results indicate that the content of the functions in the main chain has great influence on the CB dispersion; and the polymers containing amino groups in the main chain show better CB dispersing ability than the ones containing carboxylic groups. When the amino groups were quaternized, the dispersing ability of the polymer is improved remarkably and is similar to the commercial dispersant Disperbyk-163.
(3) Several amphiphilic polymers were designed and synthesized. The influences of the hydrophobic backbone components, the length of the backbone, the lateral chain and the content of functional groups on the CB dispersion were studied. The results indicate that the amino groups and proper contents of phenyl groups in the backbone of the amphiphilic polymer were favored for the dispersing of CB in water. Besides, polymer concentration, ion strength and pH have great influence on CB dispersion. When electrolyte is existed in the system, or the solution is acidic, CB could not be dispersed effectively. The CB dispersing ability of the optimal polymer dispersant can be equal to the commercial dispersant Disperbyk-190.
(4) Acrylic polycations were prepared via the aminolysis reaction between oligo amines and ester of PMMA. The complex capability of the polycations with plasmid DNA was evaluated by Agarose Gel Retardation Assay, TEM, DLS and Zeta potential measurements. The results indicate that all of the polycations could condense DNA compactly and form regular nanospheres. The size of the complexes is about 200nm, while the Zeta potential of the complexes is over 20mV. The results of cytotoxicity in HEK293T and HeLa cells indicate that the cytotoxicity of polyctions is much lower than that of 25 kDa PEI, and the cytotoxicity of 25 kDa PEI is 100 orders of magnitude higher than that of PMMA-g-oligoamines. The results of in vitro transfection exhibit that all of the three polycations could transfer the plasmid DNA to HEK293T and HeLa cells effectively, and the transfection efficiency is comparable to that of 25 kDa PEI. The confocal results indicate that all of the three polycations could transfer the plasmid DNA to nucleolus effectively.
(1)利用CCTP方法设计合成了支链亲水、主链疏水的阴离子型的接枝型两亲聚合物,表面张力研究发现水溶液中该两亲聚合物没有明显的临界胶束浓度(CMC),动态光散射(DLS)与透射电镜(TEM)结果表明很低浓度时体系中即有聚集体形成。同时,研究了两亲聚合物与阳离子表面活性剂CTAB、以及阴离子表面活性剂SDS之间的相互作用。结果表明该阴离子型两亲聚合物与CTAB可形成结构紧密的复合物,复合物的粒径以及Zeta电势与CTAB的浓度有关；两亲聚合物与CTAB之间主要通过阴阳离子的静电引力而发生相互作用。而在两亲聚合物-SDS体系中,研究表明尽管聚合物与SDS之间存在较为强烈的同号电荷之间的静电排斥作用,但是两亲聚合物与SDS仍然可以通过两者疏水结构之间的疏水吸引力而发生相互作用。
(2)采用类似技术路线合成了主链分别含有羧基、胺基以及季铵基的油溶性接枝聚合物,研究了羧基、胺基以及季铵基团对聚合物在二甲苯中分散炭黑能力的影响。结果表明主链中官能团的含量对炭黑的分散有较大的影响；而主链含胺基的接枝聚合物的炭黑分散能力比含羧基的样品好；通过将聚合物主链中的胺基季铵化,可大大提高接枝聚合物对炭黑的分散能力,能达到商业分散剂Disperbyk-163的炭黑分散能力。
(3)设计合成了多种主链疏水、支链亲水的两亲接枝型聚合物,研究了聚合物疏水主链的组成、亲水链和疏水链长度以及官能团含量对该聚合物在水中分散炭黑的影响。结果表明疏水主链含适量的胺基和苯基官能团均对炭黑的分散有利,胺基单体含量为疏水主链单体总量的5%时分散效果最好。此外,聚合物用量、溶液离子强度以及体系pH值对炭黑的分散均有较大的影响,当体系中有电解质存在或者溶液呈现酸性时对炭黑的分散不利。优化的聚合物分散剂所制备的炭黑分散体具有较好的静置稳定性,放置三个月仍能表现出良好的分散状态,其炭黑分散能力与商业分散剂Disperbyk-190相当。
(4)通过小分子多胺与大分子单体PMMA酯基之间的氨解反应制备了丙烯酸酯类聚阳离子(PMMA-g-oligoamines),通过琼脂糖凝胶电泳、TEM、DLS、Zeta电势研究了聚阳离子对质粒DNA的复合能力。结果表明三种聚阳离子均可以有效的和DNA形成结构紧密的复合物,复合物粒径在200nm左右,电位值则达到了20mV以上。细胞毒性结果表明三种聚阳离子对HEK293T和HeLa细胞的细胞毒性远远低于25 kDa PEI的毒性(25 kDa PEI的毒性为合成的聚阳离子毒性的100多倍)。对细胞的体外转染结果表明三种聚阳离子均可以把质粒DNA有效地转入HEK293T和HeLa细胞中,且在两种细胞中的转染效率达到了25 kDa PEI的转染效率。此外,激光共聚焦结果表明三种聚阳离子均可以有效的把质粒DNA转入到细胞核中。
Amphiphilic polymers have attracted much attention in the past because of their special aggregating behavior in bulk, selected solvents and surfaces. Normally, there are two different kinds of polymeric chains co-existed in amphiphilic polymer structures, which show different affinity to the two different phases (e.g. water and oil, two kinds of oils or solids with different characters). In this thesis, we focused on graft acrylic polymers (one of the widely industrial utilized amphiphilic polymers), which were copolymerized by CCTP (catalytic chain transfer polymerization)-synthesized macromonomer and nomal acrylic monomers. Moreover, the solution behavior of amphiphilic graft polymers and the influence of small surfactants (Cetyltrimethylammonium bromide (CTAB), or Sodium dodecyl sulfate (SDS)) have also been studied systematically. And the graft polymers with proper structures were applicated as dispersants to stabilize carbon black (CB) particles in xylene or water. Besides, graft polycations were synthesized via the aminolysis reaction between oligoamines and CCTP macromonomer; and the cytotoxicity, ability for complexeing with plasmid DNA and efficiency for in vitro transfection of the polycations were evaluated.
(1) The anionic amphiphilic graft polymer (the main chain is hydrophobic and the side chain is hydrophilic) was prepared via CCTP method. Surface tension study indicates that the amphiphilic graft polymer has no evident critical micelle concentration (CMC). Dynamic light scattering (DLS) and transmission electron microscope (TEM) results reveal that even at extremely low concentration, there are aggregates existed in the amphiphilic polymer solution. In addition, the interactions between the anionic polymer and cationic surfactant CTAB and anionic surfactant SDS were studied. The data shown that the anionic amphiphilic polymer could interact with CTAB forming compact complexes; the size and Zeta potential of the complexes was dependent on the CTAB concentration. The interaction between the polymer and CTAB is mainly anionic-cationic electrostatic attractions. In the system of amphiphilic polymer/SDS, the studies revealed that although strong electrostatic repulsions were existed between both of them, the amphiphilic polymer could still interact with SDS by hydrophobic attractions which are originated from the hydrophobic chains of the polymer and SDS.
(2) Three kinds of oil-soluble graft polymers (containing carboxylic, amino and quaternary ammonium groups in the main chain respectively) were synthesized via the similar synthetic route, and the influences of the functional groups on the abilities of the polymers to disperse CB in xylene were evaluated. The results indicate that the content of the functions in the main chain has great influence on the CB dispersion; and the polymers containing amino groups in the main chain show better CB dispersing ability than the ones containing carboxylic groups. When the amino groups were quaternized, the dispersing ability of the polymer is improved remarkably and is similar to the commercial dispersant Disperbyk-163.
(3) Several amphiphilic polymers were designed and synthesized. The influences of the hydrophobic backbone components, the length of the backbone, the lateral chain and the content of functional groups on the CB dispersion were studied. The results indicate that the amino groups and proper contents of phenyl groups in the backbone of the amphiphilic polymer were favored for the dispersing of CB in water. Besides, polymer concentration, ion strength and pH have great influence on CB dispersion. When electrolyte is existed in the system, or the solution is acidic, CB could not be dispersed effectively. The CB dispersing ability of the optimal polymer dispersant can be equal to the commercial dispersant Disperbyk-190.
(4) Acrylic polycations were prepared via the aminolysis reaction between oligo amines and ester of PMMA. The complex capability of the polycations with plasmid DNA was evaluated by Agarose Gel Retardation Assay, TEM, DLS and Zeta potential measurements. The results indicate that all of the polycations could condense DNA compactly and form regular nanospheres. The size of the complexes is about 200nm, while the Zeta potential of the complexes is over 20mV. The results of cytotoxicity in HEK293T and HeLa cells indicate that the cytotoxicity of polyctions is much lower than that of 25 kDa PEI, and the cytotoxicity of 25 kDa PEI is 100 orders of magnitude higher than that of PMMA-g-oligoamines. The results of in vitro transfection exhibit that all of the three polycations could transfer the plasmid DNA to HEK293T and HeLa cells effectively, and the transfection efficiency is comparable to that of 25 kDa PEI. The confocal results indicate that all of the three polycations could transfer the plasmid DNA to nucleolus effectively.
引文
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