基于聚（N，N-二乙基丙烯酰胺）的温度和pH值敏感性水凝胶的合成及其性能研究
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摘要
本论文以N,N-二乙基丙烯酰胺(DEA)为温度敏感性单体,以亲水性的N-羟甲基丙烯酰胺(NHMAA)、甲基丙烯酸二甲氨基乙酯(DMAEMA)、高分子电解质聚二烯丙基二甲基氯化铵(PDADMAC)、天然高分子卡拉胶(KC)和甲基丙烯酸(MAA)为功能单体,分别采用自由基无规共聚、接枝、互穿网络聚合方法,先后制备了具有温度和温度/pH值双重敏感性水凝胶,系统地研究了水凝胶的相转变行为、溶胀和退溶胀速率以及对模型药物的控释行为。论文取得的主要结果有：
1.通过改变单体的组成比、交联剂的量及单体的总浓度,制得了温度响应性和力学性能较好的聚(N,N-二乙基丙烯酰胺-co-N-羟甲基丙烯酰胺)(P(DEA-co-NHMAA))水凝胶。傅立叶变换红外光谱(FTIR)说明,P(DEA-co-NHMAA)凝胶被成功制备。扫描电子显微镜(SEM)结果表明,凝胶网络结构与凝胶组成和后处理有关。与PDEA相比,P(DEA-co-NHMAA)水凝胶的平衡溶胀比(ESR)和相转变温度(LCST)随NHMAA含量增加而增大。模型药物氨茶碱的释放实验结果表明,NHMAA的存在降低了氨茶碱的释放速率；同时这种释放速率受温度影响,温度越高,释放速率越慢。此外,用Peppa's势能方程分析了凝胶内药物的释放机理。
2.用自由基聚合的方法,合成了组成不同的聚(N,N-二乙基丙烯酰胺-co-甲基丙烯酸二甲氨基乙酯)(P(DEA-co-DMAEMA))温度/pH值双重敏感性水凝胶。傅立叶变换红外光谱(FTIR)与元素分析说明,P(DEA-co-DMAEMA)水凝胶被成功制备。扫描电子显微镜(SEM)观察到了凝胶网络结构与凝胶组成有关,引入DMAEMA后,使凝胶网络具有相互连接的孔结构。在一定浓度范围内,P(DEA-co-DMAEMA)水凝胶的温度和pH值敏感性能力随DMAEMA含量增加而提高,且溶胀／退溶胀速率也增大。用Peppa's势能方程分析凝胶溶胀机理发现：随着凝胶中DMAEMA含量增加,溶胀机理从Fickian扩散向Non-Fickian扩散转变。通过MTT实验发现,P(DEA-co-DMAEMA)和PDEA凝胶对HeLa细胞基本没有毒性。以牛血清蛋白为模型药物,DMAEMA的存在提高了凝胶的装载效率,降低了释放速率。同时,这种释放速率受温度影响,温度越高,释放速率越慢。这种无毒的敏感性水凝胶在药物控释等领域有潜在的用途。
3.利用大分子单体,采用自由基溶液聚合,合成了温度/pH值敏感性梳型接枝水凝胶,即在P(DEA-co-DMAEMA)凝胶的网络结构中引入一端可自由运动的P(DEA-co-DMAEMA)接枝链,且主链和支链的组分比相同。1H NMR, FTIR和GPC结果说明,大单体P(DEA-co-DMAEMA)被成功制备。扫描电子显微镜(SEM)观察到,由于接枝长链存在一定的刚性结构,凝胶网络具有相互连接的大孔结构。这种含有可自由运动接枝链的相互连接的大孔凝胶网络具有优异的温度和pH值敏感性,溶胀／退溶胀速率及可逆刺激响应行为得到很大的提高。
4.在高分子电解质聚二烯丙基二甲基氯化铵(PDADMAC)水溶液中,用自由基聚合法引发DEA聚合,得到了具有温度/pH值双重敏感性的PDADMAC/PDEA Semi-IPN水凝胶。示差扫描量热(DSC)分析结果表明,随着凝胶中PDADMAC含量的增加,网络与水形成氢键的能力增加,非冻结水含量也增加。溶胀行为研究表明,Semi-IPN水凝胶具有优良的温度和pH值敏感性,扫描电子显微镜观察的结果也证实了这一结论。同时,该凝胶还具有快的去溶胀速率和优异的可逆刺激响应行为。用Peppa's势能方程分析凝胶溶胀机理发现,随着凝胶中PDADMAC含量增加,溶胀机理从Fickian扩散向Non-Fickian扩散转变。
5.利用IPN技术,将天然多糖卡拉胶(KC)的衍生物KC-g-PMAA引入PDEA网络中,制得了KC-g-PMAA/PDEA Semi-IPN水凝胶。傅立叶变换红外光谱(FTIR)结果说明,KC-g-PMAA及Semi-IPN凝胶被成功制备。由于网络为Semi-IPN结构,所有凝胶的LCST相同。溶胀行为研究表明,Semi-IPN水凝胶具有优良的温度和pH值敏感性,且具有快的去溶胀速率,扫描电子显微镜观察的结果也证实了这一结论。用Peppa's势能方程分析凝胶溶胀机理发现,随凝胶中KC-g-PMAA含量增加,溶胀机理从Fickian扩散向Non-Fickian扩散转变。当KC-g-PMAA超过一定值,凝胶溶胀过程比较复杂,存在过溶胀现象。
In this thesis, five different kinds of hydrogel, P(N,N-diethylacrylamide-co-N-hydroxymethyl acrylamide) (P(DEA-co-NHMAA)) hydrogel, P(N,N-diethyl-acrylamide-co-(2-dimethylamino) ethyl methacrylate) (P(DEA-co-DMAEMA)) hydrogel, P(DEA-co-DMAEMA)-g-P(DEA-co-DMAEMA) hydrogel, poly(diallyldimethyl- ammonium chloride)/poly(N,N-diethylacrylamide) (PDADMAC/PDEA) semi-IPN hydrogel, carrageenan-g-poly(methacrylic acid)/poly(N,N-diethylacrylamide) (KC-g- PMAA/PDEA), were prepared using free radical solution polymerization, macro- monomer grafting polymerization and semi-interpenetrating polymerization. The effects of the feed components, temperature and pH on the swelling behavior of the hydrogels were studied, and the rapid response properties of the hydrogels were investigated in detail, and the results are summarized as following:
1. P(N,N-diethylacrylamide-co-N-hydroxymethyl acrylamide) (P(DEA-co-NHMAA)) hydrogels were synthesized by changing the initial DEA/NHMAA mole ratio, N,N'-methylenebisacrylamide and total monomer concentration. At FTIR spectra, it can be concluded that the P(DEA-co-NHMAA) hydrogel was successfully prepared. The interior morphology of the hydrogels illustrates the dependence of the morphology on the hydrogel compositions. In comparison with the PDEA hydrogel, the equilibrium swelling ratio (ESR) and lower critical solution temperature (LCST) of the hydrogels increase with the increase of NHMAA content in the feed. The release behaviors of the model drug, aminophylline, are found dependent on hydrogel composition and environmental temperature. In addition, the drug release mechanism of the drug-loaded hydrogels was analyzed by Peppa's potential equation.
2. P(N,N-diethylacrylamide-co-(2-dimethylamino) ethyl methacrylate) (P(DEA-co-DAMEMA)) hydrogels were synthesized by changing the initial DEA/DAMEMA mole ratio. The hydrogels were characterized using Fourier transform infrared (FTIR) spectroscope, elemental analysis method and scanning electron microscope (SEM). It can be concluded that the P(DEA-co-NHMAA) semi-IPN hydrogel was successfully prepared. The P(DEA-co-DMAEMA) hydrogels have porous structure with more interconnected channel-like pores surrounded with thin walls and presented a sponge-like morphology. The capability of the temperature and pH of stimulating hydrogels is enhanced when the content of DMAEMA in the hydrogels increases. In comparison with the PDEA hydrogel, the deswelling and reswelling rates of the hydrogels increase with the increase of DAMEMA content in the feed. PDEA and P(DEA-co-DMAEMA) have no apparent cytotoxicity. The absorb and release behaviors of the model drug, bovine serum albumin, were found dependent on hydrogel compositions and environmental temperature, which suggests that these materials have potential application as intelligent drug carriers.
3. The dual sensitive comb-type grafted hydrogels were synthesized by grafting polymeric chains with freely mobile ends, which were composed of both N,N-diethylacrylamide (DEA) and (2-dimethylamino) ethyl methacrylate (DMAEMA), onto the backbone of crosslinked P(DEA-co-DMAEMA) networks. The structure of the poly(DEA-co-DMAEMA) macromonomer was characterized by Nuclear Magnetic Resonance (1H NMR) and Fourier transform infrared spectroscopy (FTIR). The experiment results show that the P(DEA-co-DMAEMA) macromonomer was successfully prepared. Due to the pendant poly(DEA-co-DMAEMA) grafts providing spatial hindrance, the G-PDD hydrogels have an interconnected and macroporous network structure. The G-PDD hydrogels exhibite improved thermo- and pH-sensitive characteristics, such as faster deswelling and reswelling rates and great oscillating deswelling/swelling behavior, and the level of improvement depends on the poly(DEA-co-DMAEMA) macromonomer content.
4. A novel semi-interpenetrating polymer network (semi-IPN) hydrogel of poly(diallyldimethylammonium chloride)/poly(N,N-diethylacrylamide) (PDADMAC/ PDEA) was prepared at room temperature. Differential scanning calorimetry (DSC) studies show that the freezing water content is found to accumulate with the increasing concentration in PDADMAC, which means a raise in hydrogen bond formation between the hydrophilic chains and the water molecules. The semi-IPN hydrogels exhibite improved thermosensitive characteristics, such as faster deswelling and swelling rates and great oscillating deswelling-swelling behavior, and the level of improvement depends on the PDADMAC content. The swelling dynamic transport of the hydrogels was analyzed based on the Fickian equation. These results show that the swelling mechanism would be transformed from Fickian diffusion to non-Fickian transport.
5. A novel semi-interpenetrating polymer network (semi-IPN) hydrogel of kappa-carrageenan-g-poly(methacrylic acid)/poly(N,N-diethylacrylamide) (KC-g-PMAA/PDEA) was prepared. At FTIR spectra, it can be concluded that the KC-g-PMAA and Semi-IPN hydrogel was successfully prepared. The results show that the introduction of KC-g-PMAA do not change the lower critical solution temperature of the semi-IPN hydrogels, which is the same to the PDEA hydrogel (at 31℃). With the increase of KC-g-PMAA content, the thermo- and pH-sensitivity of the hydrogel are improved, which the swelling rate increases with the increasing content of KC-g-PMAA. The semi-IPN hydrogels show a faster deswelling and swelling rate. The swelling dynamic transport of the hydrogels was analyzed based on the Fickian equation. These results show that the swelling mechanism would be transformed from Fickian diffusion to non-Fickian transport. As the KC-g-PMAA content increase to some extent, Semi-IPN hydrogel swelling process would be more complicated, since it exhibits an overshooting phenomenon.
1.通过改变单体的组成比、交联剂的量及单体的总浓度,制得了温度响应性和力学性能较好的聚(N,N-二乙基丙烯酰胺-co-N-羟甲基丙烯酰胺)(P(DEA-co-NHMAA))水凝胶。傅立叶变换红外光谱(FTIR)说明,P(DEA-co-NHMAA)凝胶被成功制备。扫描电子显微镜(SEM)结果表明,凝胶网络结构与凝胶组成和后处理有关。与PDEA相比,P(DEA-co-NHMAA)水凝胶的平衡溶胀比(ESR)和相转变温度(LCST)随NHMAA含量增加而增大。模型药物氨茶碱的释放实验结果表明,NHMAA的存在降低了氨茶碱的释放速率；同时这种释放速率受温度影响,温度越高,释放速率越慢。此外,用Peppa's势能方程分析了凝胶内药物的释放机理。
2.用自由基聚合的方法,合成了组成不同的聚(N,N-二乙基丙烯酰胺-co-甲基丙烯酸二甲氨基乙酯)(P(DEA-co-DMAEMA))温度/pH值双重敏感性水凝胶。傅立叶变换红外光谱(FTIR)与元素分析说明,P(DEA-co-DMAEMA)水凝胶被成功制备。扫描电子显微镜(SEM)观察到了凝胶网络结构与凝胶组成有关,引入DMAEMA后,使凝胶网络具有相互连接的孔结构。在一定浓度范围内,P(DEA-co-DMAEMA)水凝胶的温度和pH值敏感性能力随DMAEMA含量增加而提高,且溶胀／退溶胀速率也增大。用Peppa's势能方程分析凝胶溶胀机理发现：随着凝胶中DMAEMA含量增加,溶胀机理从Fickian扩散向Non-Fickian扩散转变。通过MTT实验发现,P(DEA-co-DMAEMA)和PDEA凝胶对HeLa细胞基本没有毒性。以牛血清蛋白为模型药物,DMAEMA的存在提高了凝胶的装载效率,降低了释放速率。同时,这种释放速率受温度影响,温度越高,释放速率越慢。这种无毒的敏感性水凝胶在药物控释等领域有潜在的用途。
3.利用大分子单体,采用自由基溶液聚合,合成了温度/pH值敏感性梳型接枝水凝胶,即在P(DEA-co-DMAEMA)凝胶的网络结构中引入一端可自由运动的P(DEA-co-DMAEMA)接枝链,且主链和支链的组分比相同。1H NMR, FTIR和GPC结果说明,大单体P(DEA-co-DMAEMA)被成功制备。扫描电子显微镜(SEM)观察到,由于接枝长链存在一定的刚性结构,凝胶网络具有相互连接的大孔结构。这种含有可自由运动接枝链的相互连接的大孔凝胶网络具有优异的温度和pH值敏感性,溶胀／退溶胀速率及可逆刺激响应行为得到很大的提高。
4.在高分子电解质聚二烯丙基二甲基氯化铵(PDADMAC)水溶液中,用自由基聚合法引发DEA聚合,得到了具有温度/pH值双重敏感性的PDADMAC/PDEA Semi-IPN水凝胶。示差扫描量热(DSC)分析结果表明,随着凝胶中PDADMAC含量的增加,网络与水形成氢键的能力增加,非冻结水含量也增加。溶胀行为研究表明,Semi-IPN水凝胶具有优良的温度和pH值敏感性,扫描电子显微镜观察的结果也证实了这一结论。同时,该凝胶还具有快的去溶胀速率和优异的可逆刺激响应行为。用Peppa's势能方程分析凝胶溶胀机理发现,随着凝胶中PDADMAC含量增加,溶胀机理从Fickian扩散向Non-Fickian扩散转变。
5.利用IPN技术,将天然多糖卡拉胶(KC)的衍生物KC-g-PMAA引入PDEA网络中,制得了KC-g-PMAA/PDEA Semi-IPN水凝胶。傅立叶变换红外光谱(FTIR)结果说明,KC-g-PMAA及Semi-IPN凝胶被成功制备。由于网络为Semi-IPN结构,所有凝胶的LCST相同。溶胀行为研究表明,Semi-IPN水凝胶具有优良的温度和pH值敏感性,且具有快的去溶胀速率,扫描电子显微镜观察的结果也证实了这一结论。用Peppa's势能方程分析凝胶溶胀机理发现,随凝胶中KC-g-PMAA含量增加,溶胀机理从Fickian扩散向Non-Fickian扩散转变。当KC-g-PMAA超过一定值,凝胶溶胀过程比较复杂,存在过溶胀现象。
In this thesis, five different kinds of hydrogel, P(N,N-diethylacrylamide-co-N-hydroxymethyl acrylamide) (P(DEA-co-NHMAA)) hydrogel, P(N,N-diethyl-acrylamide-co-(2-dimethylamino) ethyl methacrylate) (P(DEA-co-DMAEMA)) hydrogel, P(DEA-co-DMAEMA)-g-P(DEA-co-DMAEMA) hydrogel, poly(diallyldimethyl- ammonium chloride)/poly(N,N-diethylacrylamide) (PDADMAC/PDEA) semi-IPN hydrogel, carrageenan-g-poly(methacrylic acid)/poly(N,N-diethylacrylamide) (KC-g- PMAA/PDEA), were prepared using free radical solution polymerization, macro- monomer grafting polymerization and semi-interpenetrating polymerization. The effects of the feed components, temperature and pH on the swelling behavior of the hydrogels were studied, and the rapid response properties of the hydrogels were investigated in detail, and the results are summarized as following:
1. P(N,N-diethylacrylamide-co-N-hydroxymethyl acrylamide) (P(DEA-co-NHMAA)) hydrogels were synthesized by changing the initial DEA/NHMAA mole ratio, N,N'-methylenebisacrylamide and total monomer concentration. At FTIR spectra, it can be concluded that the P(DEA-co-NHMAA) hydrogel was successfully prepared. The interior morphology of the hydrogels illustrates the dependence of the morphology on the hydrogel compositions. In comparison with the PDEA hydrogel, the equilibrium swelling ratio (ESR) and lower critical solution temperature (LCST) of the hydrogels increase with the increase of NHMAA content in the feed. The release behaviors of the model drug, aminophylline, are found dependent on hydrogel composition and environmental temperature. In addition, the drug release mechanism of the drug-loaded hydrogels was analyzed by Peppa's potential equation.
2. P(N,N-diethylacrylamide-co-(2-dimethylamino) ethyl methacrylate) (P(DEA-co-DAMEMA)) hydrogels were synthesized by changing the initial DEA/DAMEMA mole ratio. The hydrogels were characterized using Fourier transform infrared (FTIR) spectroscope, elemental analysis method and scanning electron microscope (SEM). It can be concluded that the P(DEA-co-NHMAA) semi-IPN hydrogel was successfully prepared. The P(DEA-co-DMAEMA) hydrogels have porous structure with more interconnected channel-like pores surrounded with thin walls and presented a sponge-like morphology. The capability of the temperature and pH of stimulating hydrogels is enhanced when the content of DMAEMA in the hydrogels increases. In comparison with the PDEA hydrogel, the deswelling and reswelling rates of the hydrogels increase with the increase of DAMEMA content in the feed. PDEA and P(DEA-co-DMAEMA) have no apparent cytotoxicity. The absorb and release behaviors of the model drug, bovine serum albumin, were found dependent on hydrogel compositions and environmental temperature, which suggests that these materials have potential application as intelligent drug carriers.
3. The dual sensitive comb-type grafted hydrogels were synthesized by grafting polymeric chains with freely mobile ends, which were composed of both N,N-diethylacrylamide (DEA) and (2-dimethylamino) ethyl methacrylate (DMAEMA), onto the backbone of crosslinked P(DEA-co-DMAEMA) networks. The structure of the poly(DEA-co-DMAEMA) macromonomer was characterized by Nuclear Magnetic Resonance (1H NMR) and Fourier transform infrared spectroscopy (FTIR). The experiment results show that the P(DEA-co-DMAEMA) macromonomer was successfully prepared. Due to the pendant poly(DEA-co-DMAEMA) grafts providing spatial hindrance, the G-PDD hydrogels have an interconnected and macroporous network structure. The G-PDD hydrogels exhibite improved thermo- and pH-sensitive characteristics, such as faster deswelling and reswelling rates and great oscillating deswelling/swelling behavior, and the level of improvement depends on the poly(DEA-co-DMAEMA) macromonomer content.
4. A novel semi-interpenetrating polymer network (semi-IPN) hydrogel of poly(diallyldimethylammonium chloride)/poly(N,N-diethylacrylamide) (PDADMAC/ PDEA) was prepared at room temperature. Differential scanning calorimetry (DSC) studies show that the freezing water content is found to accumulate with the increasing concentration in PDADMAC, which means a raise in hydrogen bond formation between the hydrophilic chains and the water molecules. The semi-IPN hydrogels exhibite improved thermosensitive characteristics, such as faster deswelling and swelling rates and great oscillating deswelling-swelling behavior, and the level of improvement depends on the PDADMAC content. The swelling dynamic transport of the hydrogels was analyzed based on the Fickian equation. These results show that the swelling mechanism would be transformed from Fickian diffusion to non-Fickian transport.
5. A novel semi-interpenetrating polymer network (semi-IPN) hydrogel of kappa-carrageenan-g-poly(methacrylic acid)/poly(N,N-diethylacrylamide) (KC-g-PMAA/PDEA) was prepared. At FTIR spectra, it can be concluded that the KC-g-PMAA and Semi-IPN hydrogel was successfully prepared. The results show that the introduction of KC-g-PMAA do not change the lower critical solution temperature of the semi-IPN hydrogels, which is the same to the PDEA hydrogel (at 31℃). With the increase of KC-g-PMAA content, the thermo- and pH-sensitivity of the hydrogel are improved, which the swelling rate increases with the increasing content of KC-g-PMAA. The semi-IPN hydrogels show a faster deswelling and swelling rate. The swelling dynamic transport of the hydrogels was analyzed based on the Fickian equation. These results show that the swelling mechanism would be transformed from Fickian diffusion to non-Fickian transport. As the KC-g-PMAA content increase to some extent, Semi-IPN hydrogel swelling process would be more complicated, since it exhibits an overshooting phenomenon.
引文
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