聚丙烯酸型两亲接枝共聚物的合成、表征及其水溶液中自组装行为的研究
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摘要
两亲性共聚物能在水溶液中自组装形成以亲水链段为壳,疏水链段为核的胶束结构。这些特性和功能使得两亲性共聚物在纳米材料、高分子表面活性剂、生物医药材料、石油化工等领域都受到了日益广泛的关注,其基础研究和实际应用得到了不断的发展。为了研究分子结构对自组装行为的影响,从而实现对胶束形态和大小的控制,人们希望制备得到结构规整可控的聚合物,这也是现代高分子合成化学的主要发展方向。
到目前为止,对两亲性共聚物胶束行为的研究大多集中在两亲嵌段共聚物,并且几乎都是在非极性溶剂中,而对结构规整可控的两亲性接枝共聚物虽然有关合成的报道较多,但对其在水溶液中的自组装行为和表面性质的研究报道很少,水溶液中两亲接枝共聚物形态仍然是聚合物科学的困难课题之一。基于上述研究现状和发展要求,本论文设计并合成了结构规整的以聚丙烯酸为主链的两亲性接枝共聚物,并对其在水溶液中的自组装行为进行了详细的研究。具体的工作及结果如下:
1.以甲苯为溶剂,在氯化亚铜、三乙胺存在下,辛基酚聚氧乙烯醚(C_8PhEO_(10))与丙烯酰氯反应合成了辛基酚聚氧乙烯醚丙烯酸酯活性大单体(C_8PhEO_(10)Ac),通过色谱柱对粗产品进行分离提纯。同时探讨了丙烯酰氯用量、反应温度、反应时间以及加料次序对辛基酚聚氧乙烯醚转化率的影响。采用红外光谱(FT-IR)、核磁共振(~1H-NMR)、紫外光谱(UV)、荧光光谱对大分子单体结构进行了表征,测试结果表明C_8PhEO_(10)与丙烯酰氯进行反应生成了目标产物。
2.以水为溶剂,过硫酸钾为引发剂,通过自由基共聚合成了以聚丙烯酸(PAA)为主链、C_8PhEO_(10)Ac为支链的水溶性两亲接枝共聚物(PAA-g-C_8PhEO_(10)Ac)。同时探讨了单体配比、引发剂用量、聚合温度、聚合时间对共聚物分子量及其分布、单体转化率、接枝率的影响。通过FT-IR、1H-NMR、UV、荧光、凝胶渗透色谱(GPC)、热重分析(TG)和差热分析(DTA)对共聚物进行了详细的表征,证明了这种合成以聚丙烯酸为主链的接枝共聚物的方法是可行的。
3.用表面张力法测定了水溶液中共聚物的临界胶束浓度(CMC)及其相应的表面张力(γCMC),并考察了大单体的含量和无机盐对CMC及γCMC的影响;通过粘度法探讨了共聚物浓度、无机盐对PAA-g-C_8PhEO_(10)Ac溶液比浓粘度的影响;应用紫外光谱法研究了水溶液中共聚物PAA-g-C_8PhEO_(10)Ac的胶束化行为对吸收光谱的影响。结果表明,随着大单体含量的提高,CMC及γCMC依次下降,无机盐NaCl、MgCl_2的加入可以进一步降低共聚物溶液的CMC和γCMC,该类聚合物在较低浓度下具有很好的水溶性和高表面活性。
4.分别采用2-(p-甲苯胺基)-6-萘磺酸钠(TNS)、8-苯胺基-1-萘磺酸铵盐(ANS)、芘极性探针研究了水溶液中PAA-g-C_8PhEO_(10)Ac的胶束化行为,考察了大单体含量、共聚物浓度、pH值、无机盐NaCl、MgCl_2对探针荧光光谱的影响。结果表明,随着PAA-g-C_8PhEO_(10)Ac浓度的增大,探针荧光强度逐渐提高,探针所处微环境的极性降低,在共聚物浓度达到CMC时这种变化更为显著;NaCl和MgCl_2的加入使探针分子所处微环境的极性更低,有利于TNS、ANS分子产生更强的分子内扭转电荷转移(TICT)荧光,有利于芘第一振动峰强度I1与第三振动峰强度I3之比I1/I3值降低;pH值大于6.2时,随着pH值的增大,探针所处微环境极性增强。通过三种探针荧光光谱变化所得PAA-g-C_8PhEO_(10)Ac的CMC与表面张力的结果基本一致。
5.采用水杨酸-2'-乙基己基酯(EHS)氢键探针研究了PAA-g-C_8PhEO_(10)Ac两亲接枝共聚物在水溶液中的胶束化行为,探讨了共聚物浓度、pH值、NaCl、MgCl_2对EHS荧光光谱的影响。结果显示,PAA-g-C_8PhEO_(10)Ac的加入使源于分子内氢键的长波长荧光强度显著提高,且随共聚物浓度的增大而增强。达到CMC时长波长荧光强度和峰位都发生了突变;pH值pH>6.2时,随着pH值的增加,长波长荧光强度降低、短波长荧光加强;加入NaCl后长波长荧光强度略有下降;MgCl_2对EHS光谱的影响与NaCl的结果完全不同,随着PAA-g-C_8PhEO_(10)Ac浓度的提高,长波长荧光强度快速减弱,并伴有波长红移现象。通过EHS探针荧光光谱变化所得PAA-g-C_8PhEO_(10)Ac的CMC与表面张力的结果一致。
6.采用扫描电子显微镜(SEM)法和透射电子显微镜(TEM)法研究了大单体含量、共聚物浓度、pH值以及无机盐对PAA-g-C_8PhEO_(10)Ac表面形貌以及水溶液中共聚物胶束粒径和形状的影响。结果表明,PAA-g-C_8PhEO_(10)Ac的表面形貌以及水溶液中胶束的粒径和形状与共聚物浓度、pH值、离子强度等有关。浓度增大,胶束的粒径有增大的趋势,形状由球状到柱状与球状共存,再到球状的变化;NaCl的加入使胶束粒径增大,pH值增大使胶束粒径减小。这些信息使得对两亲接枝共聚物自组装的研究更为丰富,且有助于对共聚物胶束形貌和大小的控制。
In water, the amphiphilic copolymer is energetically favorable to form micelles with its hydrophobic groups forming the core and the hydrophilic groups forming the outer shell through the self-assembly. Intensive interests on the self-assembly of amphiphilic copolymers in solution have been risen due to its potential applications in nano-materials, polymeric surfactants, biomedical substances and petrochemical technology. In order to study the effect of molecular structure on self-assembly, which can help people to reality for the controlling of micellar morphology and size, people expect to get the well-defined and controlled copolymers which is the main developing direction of modern synthetic high polymer Chemist.
So far, much attention has been focused on the self assembly of amphiphilic block copolymer and most studies are performed in organic solvents. There are more reports about the synthesis of amphiphilic graft copolymer, but little descriptions were presented for the self-assembly of amphiphilic graft copolymers in aqueous solution in detail, the morphology of amphiphilic graft copolymers is till one of the dificults in polymer science. According to the state and trend , a well-defined amphiphilic graft copolymer of PAA as main chain were designed and synthesized by free radical copolymerization in our work, and the micellar formation of the amphiphilic graft copolymer in water were investigated in detail. This thesis consists of six parts.
1. A surface-active macromonomer of C_8PhEO_(10)Ac was prepared with C_8PhEO_(10) and acrylol chloride using toluene as solution in the presence of copper(I) chloride and triethylamine. The residue was further purified by column chromatography. The effects of acrylol chloride concentration, reaction temperature, reaction time and feeding order on the percentage of C_8PhEO_(10) conversion have been discussed. The copolymer exhibited the expected structure as indicated by the results of detailed characterization with FT-IR, 1H-NMR, UV and fluorescence.
2. A series of well-defined and water-soluble PAA-g-C_8PhEO_(10)Ac of PAA as main chain and C_8PhEO_(10)Ac as graft chains were synthesized by free radical copolymerization using K2S2O8 as initiator in water. The effects of monomer ratio,initiator concentration, reaction temperature, reaction time on the molecular weight and its distributions, the percentage of monomer conversion, grating and grating efficiency have been discussed. The copolymers obtained were characterized by FT-IR, 1H-NMR, UV, fluorescence, GPC, TG, DTA, the synthesis method of graft copolymer of PAA as main chain was feasible and successful.
3. The CMC and correspondingγCMC values of the graft copolymer were obtained by surface tension measurements in aqueous solution. Influences of macromonomer and inorganic salt on CMC andγCMC have been investigated. Effects of the copolymer concentration and inorganic salts on the reduced viscosity of PAA-g-C_8PhEO_(10)Ac have been discussed. Dependence of absorption spectra on the micellar behavior of PAA-g-C_8PhEO_(10)Ac in aqueous solution on was studied. It was found that the CMC andγCMC decreased with the increase in the copolymer concentration. The presence of sodium chloride and magnesium chloride results in the lower CMC andγCMC. The graft copolymer is readily soluble in water and highly surface active at much lower concentration.
4. The micellar behavior of PAA-g-C_8PhEO_(10)Ac in aqueous solution were studied by fluorescence technique using ANS, TNS and pyrene as probes. Influences of macromonomer, copolymer concentration, pH, NaCl and MgCl_2 on their fluorescence spectra were studied. The experimental results indicate that the fluorescence intensity increases with increasing concentration of AA-C_8PhEO_(10)Ac. these changes became sharper at CMC. The presence of NaCl and MgCl_2 results in the weaker polarity in micellar core and the fluorescence intensity of TICT of TNS and ANS sharply increases. The I1/I3 values of the pyrene decreases with the addition of inorganic salt; the microenvironmental polarity of the probes decreases with the rise in pH value in the range pH 6.2-8.0. The CMC of PAA-g-C_8PhEO_(10)Ac obtained by the fluorescence measurements is in a good agreement with those obtained by surface tension measurements.
5. The micellization of PAA-g-C_8PhEO_(10)Ac in water have been monitored by fluorescent technique using EHS as a probe. Influences of the copolymer concentration, pH, NaCl and MgCl_2 on the fluorescence spectrum of EHS were investigated. The addition of PAA-g-C_8PhEO_(10)Ac resultes in sharply increased emission intensity with long wavelength for EHS with intramolecular hydrogen bonding and decreased emission intensity with short wavelength for EHS with intermolecular hydrogen bonding,the fluorescence intensity increases with increasing concentration of PAA-g-C_8PhEO_(10)Ac. Great changes in the long wavelength emission intensity and the peak position were made at CMC. The short wavelength emission intensity increased and the long wavelength emission intensity decreased from pH pH6.2 to pH8.0. The long wavelength emission intensity slightly decreases in the presence of NaCl. However, the effect of MgCl2 on the fluorescence of EHS is very different from that of NaCl. The long wavelength emission intensity of EHS begins to rapidly decrease with increasing concentration of AA-C_8PhEO_(10)Ac. Furthermore the bathochromic shift appears. The CMC of PAA-g-C_8PhEO_(10)Ac obtained by fluorescence measurements of EHS is in a good agreement with that obtained by surface tension measurements.
6. The influences of copolymer concentration, pH, inorganic salts on surface topography and the shapes and sizes of PAA-g-C_8PhEO_(10)Ac micelles in water have been discussed using SEM and TEM. The results show that the micellar shapes and the sizes were dependent on copolymer concentration, pH and ionic strength. As the copolymer concentration increases, the micellar sizes became larger. The micellar shapes undergo spherical micelles, the spherical and columnar micelles and the spherical micelles again. The sizes of micelles increased with the addition of NaCl to water and decreased at high pH values. These findings are favorable for better understanding of the self-assembly of amphiphilic graft copolymer and were helpful for control of micellar shapes and sizes.
到目前为止,对两亲性共聚物胶束行为的研究大多集中在两亲嵌段共聚物,并且几乎都是在非极性溶剂中,而对结构规整可控的两亲性接枝共聚物虽然有关合成的报道较多,但对其在水溶液中的自组装行为和表面性质的研究报道很少,水溶液中两亲接枝共聚物形态仍然是聚合物科学的困难课题之一。基于上述研究现状和发展要求,本论文设计并合成了结构规整的以聚丙烯酸为主链的两亲性接枝共聚物,并对其在水溶液中的自组装行为进行了详细的研究。具体的工作及结果如下:
1.以甲苯为溶剂,在氯化亚铜、三乙胺存在下,辛基酚聚氧乙烯醚(C_8PhEO_(10))与丙烯酰氯反应合成了辛基酚聚氧乙烯醚丙烯酸酯活性大单体(C_8PhEO_(10)Ac),通过色谱柱对粗产品进行分离提纯。同时探讨了丙烯酰氯用量、反应温度、反应时间以及加料次序对辛基酚聚氧乙烯醚转化率的影响。采用红外光谱(FT-IR)、核磁共振(~1H-NMR)、紫外光谱(UV)、荧光光谱对大分子单体结构进行了表征,测试结果表明C_8PhEO_(10)与丙烯酰氯进行反应生成了目标产物。
2.以水为溶剂,过硫酸钾为引发剂,通过自由基共聚合成了以聚丙烯酸(PAA)为主链、C_8PhEO_(10)Ac为支链的水溶性两亲接枝共聚物(PAA-g-C_8PhEO_(10)Ac)。同时探讨了单体配比、引发剂用量、聚合温度、聚合时间对共聚物分子量及其分布、单体转化率、接枝率的影响。通过FT-IR、1H-NMR、UV、荧光、凝胶渗透色谱(GPC)、热重分析(TG)和差热分析(DTA)对共聚物进行了详细的表征,证明了这种合成以聚丙烯酸为主链的接枝共聚物的方法是可行的。
3.用表面张力法测定了水溶液中共聚物的临界胶束浓度(CMC)及其相应的表面张力(γCMC),并考察了大单体的含量和无机盐对CMC及γCMC的影响;通过粘度法探讨了共聚物浓度、无机盐对PAA-g-C_8PhEO_(10)Ac溶液比浓粘度的影响;应用紫外光谱法研究了水溶液中共聚物PAA-g-C_8PhEO_(10)Ac的胶束化行为对吸收光谱的影响。结果表明,随着大单体含量的提高,CMC及γCMC依次下降,无机盐NaCl、MgCl_2的加入可以进一步降低共聚物溶液的CMC和γCMC,该类聚合物在较低浓度下具有很好的水溶性和高表面活性。
4.分别采用2-(p-甲苯胺基)-6-萘磺酸钠(TNS)、8-苯胺基-1-萘磺酸铵盐(ANS)、芘极性探针研究了水溶液中PAA-g-C_8PhEO_(10)Ac的胶束化行为,考察了大单体含量、共聚物浓度、pH值、无机盐NaCl、MgCl_2对探针荧光光谱的影响。结果表明,随着PAA-g-C_8PhEO_(10)Ac浓度的增大,探针荧光强度逐渐提高,探针所处微环境的极性降低,在共聚物浓度达到CMC时这种变化更为显著;NaCl和MgCl_2的加入使探针分子所处微环境的极性更低,有利于TNS、ANS分子产生更强的分子内扭转电荷转移(TICT)荧光,有利于芘第一振动峰强度I1与第三振动峰强度I3之比I1/I3值降低;pH值大于6.2时,随着pH值的增大,探针所处微环境极性增强。通过三种探针荧光光谱变化所得PAA-g-C_8PhEO_(10)Ac的CMC与表面张力的结果基本一致。
5.采用水杨酸-2'-乙基己基酯(EHS)氢键探针研究了PAA-g-C_8PhEO_(10)Ac两亲接枝共聚物在水溶液中的胶束化行为,探讨了共聚物浓度、pH值、NaCl、MgCl_2对EHS荧光光谱的影响。结果显示,PAA-g-C_8PhEO_(10)Ac的加入使源于分子内氢键的长波长荧光强度显著提高,且随共聚物浓度的增大而增强。达到CMC时长波长荧光强度和峰位都发生了突变;pH值pH>6.2时,随着pH值的增加,长波长荧光强度降低、短波长荧光加强;加入NaCl后长波长荧光强度略有下降;MgCl_2对EHS光谱的影响与NaCl的结果完全不同,随着PAA-g-C_8PhEO_(10)Ac浓度的提高,长波长荧光强度快速减弱,并伴有波长红移现象。通过EHS探针荧光光谱变化所得PAA-g-C_8PhEO_(10)Ac的CMC与表面张力的结果一致。
6.采用扫描电子显微镜(SEM)法和透射电子显微镜(TEM)法研究了大单体含量、共聚物浓度、pH值以及无机盐对PAA-g-C_8PhEO_(10)Ac表面形貌以及水溶液中共聚物胶束粒径和形状的影响。结果表明,PAA-g-C_8PhEO_(10)Ac的表面形貌以及水溶液中胶束的粒径和形状与共聚物浓度、pH值、离子强度等有关。浓度增大,胶束的粒径有增大的趋势,形状由球状到柱状与球状共存,再到球状的变化;NaCl的加入使胶束粒径增大,pH值增大使胶束粒径减小。这些信息使得对两亲接枝共聚物自组装的研究更为丰富,且有助于对共聚物胶束形貌和大小的控制。
In water, the amphiphilic copolymer is energetically favorable to form micelles with its hydrophobic groups forming the core and the hydrophilic groups forming the outer shell through the self-assembly. Intensive interests on the self-assembly of amphiphilic copolymers in solution have been risen due to its potential applications in nano-materials, polymeric surfactants, biomedical substances and petrochemical technology. In order to study the effect of molecular structure on self-assembly, which can help people to reality for the controlling of micellar morphology and size, people expect to get the well-defined and controlled copolymers which is the main developing direction of modern synthetic high polymer Chemist.
So far, much attention has been focused on the self assembly of amphiphilic block copolymer and most studies are performed in organic solvents. There are more reports about the synthesis of amphiphilic graft copolymer, but little descriptions were presented for the self-assembly of amphiphilic graft copolymers in aqueous solution in detail, the morphology of amphiphilic graft copolymers is till one of the dificults in polymer science. According to the state and trend , a well-defined amphiphilic graft copolymer of PAA as main chain were designed and synthesized by free radical copolymerization in our work, and the micellar formation of the amphiphilic graft copolymer in water were investigated in detail. This thesis consists of six parts.
1. A surface-active macromonomer of C_8PhEO_(10)Ac was prepared with C_8PhEO_(10) and acrylol chloride using toluene as solution in the presence of copper(I) chloride and triethylamine. The residue was further purified by column chromatography. The effects of acrylol chloride concentration, reaction temperature, reaction time and feeding order on the percentage of C_8PhEO_(10) conversion have been discussed. The copolymer exhibited the expected structure as indicated by the results of detailed characterization with FT-IR, 1H-NMR, UV and fluorescence.
2. A series of well-defined and water-soluble PAA-g-C_8PhEO_(10)Ac of PAA as main chain and C_8PhEO_(10)Ac as graft chains were synthesized by free radical copolymerization using K2S2O8 as initiator in water. The effects of monomer ratio,initiator concentration, reaction temperature, reaction time on the molecular weight and its distributions, the percentage of monomer conversion, grating and grating efficiency have been discussed. The copolymers obtained were characterized by FT-IR, 1H-NMR, UV, fluorescence, GPC, TG, DTA, the synthesis method of graft copolymer of PAA as main chain was feasible and successful.
3. The CMC and correspondingγCMC values of the graft copolymer were obtained by surface tension measurements in aqueous solution. Influences of macromonomer and inorganic salt on CMC andγCMC have been investigated. Effects of the copolymer concentration and inorganic salts on the reduced viscosity of PAA-g-C_8PhEO_(10)Ac have been discussed. Dependence of absorption spectra on the micellar behavior of PAA-g-C_8PhEO_(10)Ac in aqueous solution on was studied. It was found that the CMC andγCMC decreased with the increase in the copolymer concentration. The presence of sodium chloride and magnesium chloride results in the lower CMC andγCMC. The graft copolymer is readily soluble in water and highly surface active at much lower concentration.
4. The micellar behavior of PAA-g-C_8PhEO_(10)Ac in aqueous solution were studied by fluorescence technique using ANS, TNS and pyrene as probes. Influences of macromonomer, copolymer concentration, pH, NaCl and MgCl_2 on their fluorescence spectra were studied. The experimental results indicate that the fluorescence intensity increases with increasing concentration of AA-C_8PhEO_(10)Ac. these changes became sharper at CMC. The presence of NaCl and MgCl_2 results in the weaker polarity in micellar core and the fluorescence intensity of TICT of TNS and ANS sharply increases. The I1/I3 values of the pyrene decreases with the addition of inorganic salt; the microenvironmental polarity of the probes decreases with the rise in pH value in the range pH 6.2-8.0. The CMC of PAA-g-C_8PhEO_(10)Ac obtained by the fluorescence measurements is in a good agreement with those obtained by surface tension measurements.
5. The micellization of PAA-g-C_8PhEO_(10)Ac in water have been monitored by fluorescent technique using EHS as a probe. Influences of the copolymer concentration, pH, NaCl and MgCl_2 on the fluorescence spectrum of EHS were investigated. The addition of PAA-g-C_8PhEO_(10)Ac resultes in sharply increased emission intensity with long wavelength for EHS with intramolecular hydrogen bonding and decreased emission intensity with short wavelength for EHS with intermolecular hydrogen bonding,the fluorescence intensity increases with increasing concentration of PAA-g-C_8PhEO_(10)Ac. Great changes in the long wavelength emission intensity and the peak position were made at CMC. The short wavelength emission intensity increased and the long wavelength emission intensity decreased from pH pH6.2 to pH8.0. The long wavelength emission intensity slightly decreases in the presence of NaCl. However, the effect of MgCl2 on the fluorescence of EHS is very different from that of NaCl. The long wavelength emission intensity of EHS begins to rapidly decrease with increasing concentration of AA-C_8PhEO_(10)Ac. Furthermore the bathochromic shift appears. The CMC of PAA-g-C_8PhEO_(10)Ac obtained by fluorescence measurements of EHS is in a good agreement with that obtained by surface tension measurements.
6. The influences of copolymer concentration, pH, inorganic salts on surface topography and the shapes and sizes of PAA-g-C_8PhEO_(10)Ac micelles in water have been discussed using SEM and TEM. The results show that the micellar shapes and the sizes were dependent on copolymer concentration, pH and ionic strength. As the copolymer concentration increases, the micellar sizes became larger. The micellar shapes undergo spherical micelles, the spherical and columnar micelles and the spherical micelles again. The sizes of micelles increased with the addition of NaCl to water and decreased at high pH values. These findings are favorable for better understanding of the self-assembly of amphiphilic graft copolymer and were helpful for control of micellar shapes and sizes.
引文
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