单分散磁性聚合物复合微球的制备及表面亲水性聚合物的修饰
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摘要
随着制备技术的发展,聚合物乳液及微球的应用范围日益广泛,从最早的应用于涂料、纸张、胶粘剂、塑料添加物、建筑材料等一直到近几十年来的医疗和医药领域、生物化学领域。聚合物微球通常可通过乳液聚合方法直接制备,但这些微球往往不能直接满足应用要求,通常需要对聚合物微球进行表面修饰。在本论文中,我们首先采用无皂乳液聚合法制备了不同尺寸的表面带环氧基团的聚(甲基丙烯酸甲酯-甲基丙烯酸缩水甘油酯-二乙烯基苯)P(MMA-GMA-DVB)(P(MGD))聚合物共聚微球,然后在微球表面接枝树枝状聚酰胺胺(d-PAMAM),利用d-PAMAM的氨基键合荧光素后得到了不同尺寸的荧光微球。在此基础上,用无皂乳液聚合的方法制备了磁性聚合物微球,然后在微球表面接枝d-PAMAM,利用d-PAMAM的氨基键合荧光素得到了磁性、PH敏感和荧光多功能的复合微球。最后,初步研究了用可生物降解的聚天冬酰胺衍生物对聚合物微球的修饰,以增加聚合物微球的生物相容性。具体研究内容如下:
(1)采用无皂乳液聚合及种子聚合方法制备了200～800 nm四种不同尺寸的单分散PMGD复合微球,用扫描电镜(SEM)和动态光散射(DLS)对其进行了表征。实验中发现单体滴加速度是影响种子滴加聚合过程二次成核的关键因素。用乙二胺对微球表面的环氧基团开环后,在微球表面接枝d-PAMAM,增加了微球表面的官能团密度及提高了微球水中的分散稳定性。元素分析(EA)和红外光谱(FTIR)实验证明了微球表面d-PAMAM的存在。最后利用d-PAMAM的氨基键合荧光素四甲基异硫氰酸罗丹明(TRITC)后得到四种尺寸的水分散性的红色荧光微球。
(2)用两步法制备了双层油酸稳定的Fe_3O_4纳米粒子,然后在纳米粒子的存在下进行甲基丙烯酸甲酯(MMA)和二乙烯基苯(DVB)的无皂乳液聚合制备了聚合物磁性微球Fe_3O_4@P(MMA-DVB),综合考察了聚合单体中DVB的用量、磁流体分散液中氨水、油酸的量对磁性微球粒径大小以及形态的影响。接着以Fe_3O_4@P(MMA-DVB)为种子,进行甲基丙烯酸羟乙酯(HEMA)、甲基丙烯酸缩水甘油酯(GMA)、甲基丙烯酸叔丁酯(t-BMA)、苯乙烯(St)和N-异丙基丙烯酰胺(NIPAM)的种子乳液聚合,得到了表面为羟基、环氧基、叔丁酯基、表面疏水和具有温敏特性的磁性聚合物复合微球。以表面为环氧基的磁性聚合物微球为模板,在微球表面接枝d-PAMAM,最后利用d-PAMAM的氨基同荧光素FITC键合制备了磁性、PH敏感和荧光多功能的复合微球。
(3)用无皂乳液聚合的方法制备了PMGD复合微球,以磷酸为催化剂,1,3,5-三甲苯/环丁砜为溶剂制备了聚琥珀酰亚胺(PSI):分别在PSI的良溶剂(DMF)和不良溶剂(H_2O)中在PMGD微球表面接枝PSI。(a)在DMF中接枝:我们分别制备了交联度为20、30、40、50 Wt%的PMGD微球,然后在DMF中在各种交联度的PMGD微球表面接枝PSI。(b)在H_2O中接枝:制备了交联度为10wt%的PMGD微球,用羟乙胺对PSI进行部分开环后得到了溶于水的PSI-OH,然后在水中在PMGD微球表面接枝PSI-OH。接枝完后,用过量的乙二胺将微球表面PSI中剩余的丁酰亚胺环打开。
With the development of the technique in preparation of polymer latex,the applications of latex and microspheres have been broadened from earlier industry field such as coatings,papers,adhesive,plastic additives and architecture materials to biomedical and biochemical fields.Polymer microspheres were usually prepared by emulsion polymerization,but when the polymer micrsopheres directly prepared by emulsion polymerization can not be satisfied with the requirment,surface modification of the as-prepared microspheres was necessary to prepare functional polymer micropheres.In this thesis,we prepared three kinds of multifunctional polymer microspheres:(1) We prepared different-sized P(MMA-GMA-DVB) (PMGD)micropsheres modified by dendritic PAMAM(d-PAMAM) at first,and then red fluorescent microspheres were achieved by attachment of TRITC to the surface of microspheres;(2) The magnetic microspheres modified by d-PAMAM were prepared, and then FITC was attached to give the micropsheres fluorescent property;(3) The microspheres modified by polyasparagine derivatives were prepared to enhance the biocompatibility.The results of each part were listed as follows:
(1) Mono-dispersed PMGD microspheres with size ranging from 200 to 800 nm were synthesized by soap-free emulsion polymerization and seeded polymerization. The as-prepared microspheres were aminated by ethylenediamine.Afterwards, different generations of d-PAMAM were grafted onto the surface of the microspheres by repeated Michael additions and amination reactions,at last different-sized water-dispersible microspheres with red fluorescence could be prepared by covalently coupling tetramethyl rhodamine isothiocyanate(TRITC).
(2) Different kinds of magnetic fluids were firstly prepared through changing the content of oleic acid and ammonia solution to disperse the monolayer-oleic acid-stabilized magnetite particles.Then magnetic polymer microspheres were prepared by soap-free emulsion copolymerization of methyl methacrylate and divinylbenzene in the presence of above magnetic fluids.The effects of various polymerization parameters such as the content of oleic acid,ammonia solution in the dispersion solution and the content of divinylbenzene on the morphology and size of the magnetic microspheres were investigated in detail.The magnetic functional microspheres were obtained by seeded emulsion polymerization of 2-Hydroxyethyl methacrylate(HEMA),tert-butyl methacrylate(t-BMA),N-isopropylacrylamide (NIPAM),glycidyl methacrylate(GMA) and styrene(St) using the Fe_3O_4@P(MMA-DVB) microspheres as seeds.At last,multifunctional microspheres with superparamagnetic,pH-sensitive,and photoluminescence properties were achieved by the following procedure:(a) the chemical modification of the PMGD shells with ethylenediamine(EDA) to yield amino groups;(b) the dendritic poly(amidoamine)(PAMAM) shells were coated on the magnetic particles on the basis of the Michael addition of methyl acrylate and amidation of the resulting ester with large excesses of EDA,which could achieve generational growth under such uniform stepwise reactions;(c)(FITC),which is a popular organic dye,was reacted with the terminal -NH2 groups from the dendritic PAMAM shells
(3) Mono-dispersed PMGD microspheres were prepared by soap-free emulsion polymerization and polysuccinimide(PSI) were prepared by polycondensation of L-aspartic acid(L-ASP) using phosphoric acid as a catalyst in sulfolane/mesitylene. Then,PSI was attached to the surface of PMGD microspheres in N,N-dimethylformamide(DMF) and deionized water,respectively.(a) Grafting in DMF solution:PMGD microspheres with different content of DVB were prepared first and then was aminated by EDA,then PSI was attached to the surface of PMGD microspheres through the reaction between the amino groups of mcirospheres and highly chemical reactive loops of PSI;(b) Grafting in water:PMGD microspheres with 10 wt%of DVB were prepared at first,then these microspheres were aminated by EDA,finally,the PMGD microspheres modified by polyasparagine derivatives were achieved.Element analysis was used to characterize the finial microspheres.
(1)采用无皂乳液聚合及种子聚合方法制备了200～800 nm四种不同尺寸的单分散PMGD复合微球,用扫描电镜(SEM)和动态光散射(DLS)对其进行了表征。实验中发现单体滴加速度是影响种子滴加聚合过程二次成核的关键因素。用乙二胺对微球表面的环氧基团开环后,在微球表面接枝d-PAMAM,增加了微球表面的官能团密度及提高了微球水中的分散稳定性。元素分析(EA)和红外光谱(FTIR)实验证明了微球表面d-PAMAM的存在。最后利用d-PAMAM的氨基键合荧光素四甲基异硫氰酸罗丹明(TRITC)后得到四种尺寸的水分散性的红色荧光微球。
(2)用两步法制备了双层油酸稳定的Fe_3O_4纳米粒子,然后在纳米粒子的存在下进行甲基丙烯酸甲酯(MMA)和二乙烯基苯(DVB)的无皂乳液聚合制备了聚合物磁性微球Fe_3O_4@P(MMA-DVB),综合考察了聚合单体中DVB的用量、磁流体分散液中氨水、油酸的量对磁性微球粒径大小以及形态的影响。接着以Fe_3O_4@P(MMA-DVB)为种子,进行甲基丙烯酸羟乙酯(HEMA)、甲基丙烯酸缩水甘油酯(GMA)、甲基丙烯酸叔丁酯(t-BMA)、苯乙烯(St)和N-异丙基丙烯酰胺(NIPAM)的种子乳液聚合,得到了表面为羟基、环氧基、叔丁酯基、表面疏水和具有温敏特性的磁性聚合物复合微球。以表面为环氧基的磁性聚合物微球为模板,在微球表面接枝d-PAMAM,最后利用d-PAMAM的氨基同荧光素FITC键合制备了磁性、PH敏感和荧光多功能的复合微球。
(3)用无皂乳液聚合的方法制备了PMGD复合微球,以磷酸为催化剂,1,3,5-三甲苯/环丁砜为溶剂制备了聚琥珀酰亚胺(PSI):分别在PSI的良溶剂(DMF)和不良溶剂(H_2O)中在PMGD微球表面接枝PSI。(a)在DMF中接枝:我们分别制备了交联度为20、30、40、50 Wt%的PMGD微球,然后在DMF中在各种交联度的PMGD微球表面接枝PSI。(b)在H_2O中接枝:制备了交联度为10wt%的PMGD微球,用羟乙胺对PSI进行部分开环后得到了溶于水的PSI-OH,然后在水中在PMGD微球表面接枝PSI-OH。接枝完后,用过量的乙二胺将微球表面PSI中剩余的丁酰亚胺环打开。
With the development of the technique in preparation of polymer latex,the applications of latex and microspheres have been broadened from earlier industry field such as coatings,papers,adhesive,plastic additives and architecture materials to biomedical and biochemical fields.Polymer microspheres were usually prepared by emulsion polymerization,but when the polymer micrsopheres directly prepared by emulsion polymerization can not be satisfied with the requirment,surface modification of the as-prepared microspheres was necessary to prepare functional polymer micropheres.In this thesis,we prepared three kinds of multifunctional polymer microspheres:(1) We prepared different-sized P(MMA-GMA-DVB) (PMGD)micropsheres modified by dendritic PAMAM(d-PAMAM) at first,and then red fluorescent microspheres were achieved by attachment of TRITC to the surface of microspheres;(2) The magnetic microspheres modified by d-PAMAM were prepared, and then FITC was attached to give the micropsheres fluorescent property;(3) The microspheres modified by polyasparagine derivatives were prepared to enhance the biocompatibility.The results of each part were listed as follows:
(1) Mono-dispersed PMGD microspheres with size ranging from 200 to 800 nm were synthesized by soap-free emulsion polymerization and seeded polymerization. The as-prepared microspheres were aminated by ethylenediamine.Afterwards, different generations of d-PAMAM were grafted onto the surface of the microspheres by repeated Michael additions and amination reactions,at last different-sized water-dispersible microspheres with red fluorescence could be prepared by covalently coupling tetramethyl rhodamine isothiocyanate(TRITC).
(2) Different kinds of magnetic fluids were firstly prepared through changing the content of oleic acid and ammonia solution to disperse the monolayer-oleic acid-stabilized magnetite particles.Then magnetic polymer microspheres were prepared by soap-free emulsion copolymerization of methyl methacrylate and divinylbenzene in the presence of above magnetic fluids.The effects of various polymerization parameters such as the content of oleic acid,ammonia solution in the dispersion solution and the content of divinylbenzene on the morphology and size of the magnetic microspheres were investigated in detail.The magnetic functional microspheres were obtained by seeded emulsion polymerization of 2-Hydroxyethyl methacrylate(HEMA),tert-butyl methacrylate(t-BMA),N-isopropylacrylamide (NIPAM),glycidyl methacrylate(GMA) and styrene(St) using the Fe_3O_4@P(MMA-DVB) microspheres as seeds.At last,multifunctional microspheres with superparamagnetic,pH-sensitive,and photoluminescence properties were achieved by the following procedure:(a) the chemical modification of the PMGD shells with ethylenediamine(EDA) to yield amino groups;(b) the dendritic poly(amidoamine)(PAMAM) shells were coated on the magnetic particles on the basis of the Michael addition of methyl acrylate and amidation of the resulting ester with large excesses of EDA,which could achieve generational growth under such uniform stepwise reactions;(c)(FITC),which is a popular organic dye,was reacted with the terminal -NH2 groups from the dendritic PAMAM shells
(3) Mono-dispersed PMGD microspheres were prepared by soap-free emulsion polymerization and polysuccinimide(PSI) were prepared by polycondensation of L-aspartic acid(L-ASP) using phosphoric acid as a catalyst in sulfolane/mesitylene. Then,PSI was attached to the surface of PMGD microspheres in N,N-dimethylformamide(DMF) and deionized water,respectively.(a) Grafting in DMF solution:PMGD microspheres with different content of DVB were prepared first and then was aminated by EDA,then PSI was attached to the surface of PMGD microspheres through the reaction between the amino groups of mcirospheres and highly chemical reactive loops of PSI;(b) Grafting in water:PMGD microspheres with 10 wt%of DVB were prepared at first,then these microspheres were aminated by EDA,finally,the PMGD microspheres modified by polyasparagine derivatives were achieved.Element analysis was used to characterize the finial microspheres.
引文
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