肉桂酸衍生物基聚酯的制备与性能研究
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摘要
对于日益严峻的资源和环境问题的解决及临床医学、生物医药等领域新材料的开发均具有重要意义，因而功能性可降解高分子的研究成为了当前的研究热点。在各种可降解高分子中，聚己内酯（PCL）及其共聚物是一类生物相容性优异、无毒且药物渗透性良好的生物可降解脂肪族聚酯，并逐渐成为了当前的研究热点。羟基肉桂酸是一类来源于植物的光敏性“植物性单体”，将二者通过不同形式的化学键键接在一起得到的光敏性聚酯可有效地对二者的性质进行互补，改善不足，发扬优点，通过对其结构、组成等的控制可实现对此类聚酯性能的调控。
本文首先通过开环聚合法制备了不同分子量的PCL均聚物，进而利用自制的PCL和4-羟基肉桂酸（4HCA）通过熔融缩聚法合成了系列PCL-co-P4HCA共聚物。利用了FTIR和1H NMR对所制备的共聚物的结构进行了确认； GPC的结果表明：PCL-co-P4HCA的分子量介于8.7×10~4-10.1×10~4g/mol之间，且分子量越大，分子量分布越宽；PCL-co-P4HCA具有光敏性，在302nm的UV照射下，共聚物在306nm处的特征吸收峰的强度逐渐下降，并最终趋于稳定，此外共聚物中4HCA单元的含量越多，光响应速度越快，光照50min后的下降程度（交联度）也越大；PCL-co-P4HCA系列共聚物均具有荧光性，随着共聚物中4HCA组分含量的减少和紫外光照时间的增加，PCL-co-P4HCA在450nm处的荧光强度呈线性减弱；DSC和WXRD的结果表明PCL-co-P4HCA共聚物兼具有PCL和P4HCA均聚物的结晶性，随着共聚物中PCL组分含量的减少，PCL-co-P4HCA的结晶度会呈现出降低的趋势；PCL-co-P4HCA具有优异的热稳定性，紫外光照会使系列共聚物的热稳定性呈规律性下降；共聚物板材表面的水接触角会随着4HCA组分的减少和紫外光照时间的增加而增大；共聚物中4HCA单元含量的增加有利于聚合物的降解，碱性条件相对于中性条件具有更快的降解速度，紫外光照会增加板材的疏水性，从而使其水解速度下降。
利用AB2型单体3,4-二羟基肉桂酸（DHCA）与自制的PCL通过聚合反应，合成了支化型的PCL-co-PDHCA共聚物，在确定了其结构后，进一步利用1H NMR对聚合物的支化度进行了分析表征， GPC和FTIR的结果表明共聚物在形成的过程中发生了酯交换反应。PCL-co-PDHCA共聚物具有光敏性，在302nm的UV光照75min后的光交联程度可达到30%左右，且DHCA单元含量越多，光交联程度越大；PCL-co-PDHCA共聚物的荧光性会受到支化度的影响，当聚合物的支化度较低时，荧光强度随DHCA组分含量的增加而增加，当支化度较高时会引起荧光猝灭的发生，从而导致荧光强度下降；DSC和WXRD的结果表明PCL-co-PDHCA共聚物的结晶性主要受到PCL的影响，随着DHCA组分含量的增加，共聚物的熔点和结晶度随下降；PCL-co-PDHCA共聚物具有优异的热稳定性，聚合物的组成、支化度和紫外光照均会对其热稳定性造成影响；PCL组分含量的增加和UV光照均会降低共聚物板材的亲水性，进而减缓水解速度。
利用无水磷酸钠作为催化剂，按照同样的投料比分别制备了直链形的P4HCA和PCL-co-P4HCA及支化型的PDHCA和PCL-co-PDHCA系列聚合物，通过FTIR和1HNMR对两种聚合物的结构进行了分析。1H NMR和GPC的结果表明AB2型单体DHCA的反应活性相对优于4HCA；在55min的UV光照后，支化型的PCL-co-PDHCA相对于直链形的PCL-co-P4HCA具有更高的光交联程度，而直链形聚合物由于分子链活动能力更强因而更容易发生顺反异构化反应；直链形的P4HCA和PCL-co-P4HCA相对于同样组成的PDHCA和PCL-co-PDHCA具有更强的荧光强度；支化型结构及更强的π-π堆叠作用使支化型的PDHCA和PCL-co-PDHCA相对于直链形聚合物具有更好的热稳定性；WXRD结果表明PCL-co-P4HCA具有更强的结晶性，这一性质使P4HCA和PCL-co-P4HCA具有相对缓慢的降解速度。
利用不同分子量的聚乙二醇（PEG）引发己内酯（CL）进行开环聚合反应制备了聚己内酯-b-聚乙二醇-b-聚己内酯（PECL）三嵌段共聚物，进而将乙酰化的4HCA（4ACA）键接到PECL的两端，制备了光敏性PECL-4ACA共聚物。DSC的结果表明PECL-4ACA共聚物具有结晶性，且PECL-4ACA的熔点随着PCL组分的增加而升高，4ACA端基抑制了PECL-4ACA中PCL链段的热分解作用，因而明显增强了PECL-4ACA的热稳定性；在302和254nm的UV照射下PECL-4ACA共聚物表现出了可逆的光敏性；PECL中PEG链段对接触角的影响占主要作用，当在PECL末端引入4ACA后，PECL-4ACA板材表面的接触角呈现出下降的趋势；共聚物的降解速度和水接触角存在对应关系，水接触角的减小会增加共聚物的降解速度。
Researches and developments of functional biodegradable polymers which play a goodrole not only in the increasingly serious problems of resources and environment but also inthe development of new materials of the clinical medicine, biomedical and other fields havebecome a current research focus. In a variety of degradable polymers, Polymers based onpolycaprolactone (PCL) have been paid more attention owing to the characteristics ofexcellent biocompatibility, biodegradability, drug permeability and nontoxicity. Hydroycinnamic acid which derived from plants is a kind of photoreactive “plant monomer”. Thephotoreactive polyesters obtained from the two monomers by different forms of chemicalbond have the concentrated properties of both the two monomers, the weakness can beimproved and the advantages can be promoted. Regulation of such polyester performance canbe achieved through the control of their structure, composition. The regulation of theproperties of these kinds of polyesters can be achieved through the control of their structuresand compositions.
In this paper, PCL homo-polymers with different molecular weight were synthesized bya ring-opening polymerization method, and then series of PCL-co-P4HCA copolymers werealso synthesized via a thermal polycondensation method using PCL and4HCA monomers.The structures of the copolymers have been confirmed by FTIR and1H NMR. The results ofGPC showed that the molecular weights of PCL-co-P4HCA were between8.7×104-10.1×104g/mol, and the molecular weight distribution would much wider when the molecularweight was higher. PCL-co-P4HCA copolymers were photoreactive, and the absorption ofthe cinnamoyl group at306nm decreased rapidly and then decreased gradually withincreasing time of302nm UV irradiation. Moreover, PCL-co-P4HCA copolymers withhigher4HCA compositions showed greater photoreactivity rates and the decline degree after50min. PCL-co-P4HCA copolymers have fluorescence properties, the maximum emissionpeak intensity at450nm of these polymers decreased linearly with a decrease in4HCAcontent and the increase time of UV irradiation. The results of DSC and WXRD showedPCL-co-P4HCA copolymers were crystalline of PCL and P4HCA homo-polymers, thecrystallinity would decrease with a decrease of PCL composition. PCL-co-P4HCAcopolymers have excellent thermal stabilities which decrease regularly when irradiated withUV rays. The water contact angles of the PCL-co-P4HCA sheets increased with a decrease in4HCA content and the increase time of UV irradiation. The hydrolysis rate of thePCL-co-P4HCA sheets increased with an increase in4HCA content, and the rates ofhydrolysis were significantly higher under alkaline conditions than under neutral conditions.The degradation rates of the copolymers after UV irradiation were slightly slower due to the higher surface hydrophobicity.
Hyprebranched PCL-co-PDHCA copolymers were obtained by thermalmelt-polycondensation of PCL and AB2type DHCA monomer. The structures and thebranching degree were identified by1H NMR, and transesterification during thepolymerization might also occur from the results of FTIR and GPC. PCL-co-PDHCAcopolymers were photoreactive, and the crosslinking degree after75min UV irradiationwhich increased with an increase of DHCA composition might achieve about30%. Thefluorescence properties of PCL-co-PDHCA will be influenced by branching degree. Theemission intensity increased with increasing of the DHCA composition under the lowerbranching degree, a high branching degree will cause the fluorescent quenched and induce adecline of the emission intensity. The results of DSC and WXRD showed the crystallinity ofPCL-co-PDHCA copolymers reflected the PCL chain mainly, and the melt point andcrystallinity would decrease with an increase of DHCA composition. PCL-co-PDHCAcopolymers have excellent thermal stabilities which will influence by polymer component,branching degree and UV irradiation. The degradation rates of copolymers sheets would slowdown by increasing the PCL composition and UV irradiation.
Linear P4HCA, PCL-co-P4HCA and hyperbranched PDHCA, PCL-co-PDHCApolymers were obtained using anhydrous sodium phosphate as a catalyst. The structures ofthe polymers have been confirmed by FTIR and1H NMR. The reactivity of AB2type DHCAis higher than4HCA. The photocrosslinking degrees of hyperbranched polymers are higherthan the one of linear polymers after55min UV irradiation. However, the linear architectureis more prone to carry out the cis-trans isomerization, and the linear polymers have strongerfluorescence intensity. Hyperbranched architectures cause the better thermal stability of thepolymers due to the stronger π-π stacking. The result of WXRD and accelerated degradationtest showed the stronger crystalline of PCL-co-P4HCA lead to the slower degradation rate.
PECL-4ACA triblock copolymers were obtained from PECL synthesized byring-opening polymerization and4ACC. The results of DSC showed the copolymers werecrystalline, and the melting point increased with the increasing of the PCL chain composition.The thermal stability of the copolymers has been enhanced owing to the4ACA terminalgroups which restrain thermal decomposition of the aliphatic polyester PCL segment.PECL-4ACA copolymers display a reversible photosensitivity under302and254nm UVirradiation. PEG chains play a dominant role in the contact angle which express declinetendency as the introduction of4ACA terminal groups. The polymers which were muchhydrophilic had the faster degradation rate.
本文首先通过开环聚合法制备了不同分子量的PCL均聚物，进而利用自制的PCL和4-羟基肉桂酸（4HCA）通过熔融缩聚法合成了系列PCL-co-P4HCA共聚物。利用了FTIR和1H NMR对所制备的共聚物的结构进行了确认； GPC的结果表明：PCL-co-P4HCA的分子量介于8.7×10~4-10.1×10~4g/mol之间，且分子量越大，分子量分布越宽；PCL-co-P4HCA具有光敏性，在302nm的UV照射下，共聚物在306nm处的特征吸收峰的强度逐渐下降，并最终趋于稳定，此外共聚物中4HCA单元的含量越多，光响应速度越快，光照50min后的下降程度（交联度）也越大；PCL-co-P4HCA系列共聚物均具有荧光性，随着共聚物中4HCA组分含量的减少和紫外光照时间的增加，PCL-co-P4HCA在450nm处的荧光强度呈线性减弱；DSC和WXRD的结果表明PCL-co-P4HCA共聚物兼具有PCL和P4HCA均聚物的结晶性，随着共聚物中PCL组分含量的减少，PCL-co-P4HCA的结晶度会呈现出降低的趋势；PCL-co-P4HCA具有优异的热稳定性，紫外光照会使系列共聚物的热稳定性呈规律性下降；共聚物板材表面的水接触角会随着4HCA组分的减少和紫外光照时间的增加而增大；共聚物中4HCA单元含量的增加有利于聚合物的降解，碱性条件相对于中性条件具有更快的降解速度，紫外光照会增加板材的疏水性，从而使其水解速度下降。
利用AB2型单体3,4-二羟基肉桂酸（DHCA）与自制的PCL通过聚合反应，合成了支化型的PCL-co-PDHCA共聚物，在确定了其结构后，进一步利用1H NMR对聚合物的支化度进行了分析表征， GPC和FTIR的结果表明共聚物在形成的过程中发生了酯交换反应。PCL-co-PDHCA共聚物具有光敏性，在302nm的UV光照75min后的光交联程度可达到30%左右，且DHCA单元含量越多，光交联程度越大；PCL-co-PDHCA共聚物的荧光性会受到支化度的影响，当聚合物的支化度较低时，荧光强度随DHCA组分含量的增加而增加，当支化度较高时会引起荧光猝灭的发生，从而导致荧光强度下降；DSC和WXRD的结果表明PCL-co-PDHCA共聚物的结晶性主要受到PCL的影响，随着DHCA组分含量的增加，共聚物的熔点和结晶度随下降；PCL-co-PDHCA共聚物具有优异的热稳定性，聚合物的组成、支化度和紫外光照均会对其热稳定性造成影响；PCL组分含量的增加和UV光照均会降低共聚物板材的亲水性，进而减缓水解速度。
利用无水磷酸钠作为催化剂，按照同样的投料比分别制备了直链形的P4HCA和PCL-co-P4HCA及支化型的PDHCA和PCL-co-PDHCA系列聚合物，通过FTIR和1HNMR对两种聚合物的结构进行了分析。1H NMR和GPC的结果表明AB2型单体DHCA的反应活性相对优于4HCA；在55min的UV光照后，支化型的PCL-co-PDHCA相对于直链形的PCL-co-P4HCA具有更高的光交联程度，而直链形聚合物由于分子链活动能力更强因而更容易发生顺反异构化反应；直链形的P4HCA和PCL-co-P4HCA相对于同样组成的PDHCA和PCL-co-PDHCA具有更强的荧光强度；支化型结构及更强的π-π堆叠作用使支化型的PDHCA和PCL-co-PDHCA相对于直链形聚合物具有更好的热稳定性；WXRD结果表明PCL-co-P4HCA具有更强的结晶性，这一性质使P4HCA和PCL-co-P4HCA具有相对缓慢的降解速度。
利用不同分子量的聚乙二醇（PEG）引发己内酯（CL）进行开环聚合反应制备了聚己内酯-b-聚乙二醇-b-聚己内酯（PECL）三嵌段共聚物，进而将乙酰化的4HCA（4ACA）键接到PECL的两端，制备了光敏性PECL-4ACA共聚物。DSC的结果表明PECL-4ACA共聚物具有结晶性，且PECL-4ACA的熔点随着PCL组分的增加而升高，4ACA端基抑制了PECL-4ACA中PCL链段的热分解作用，因而明显增强了PECL-4ACA的热稳定性；在302和254nm的UV照射下PECL-4ACA共聚物表现出了可逆的光敏性；PECL中PEG链段对接触角的影响占主要作用，当在PECL末端引入4ACA后，PECL-4ACA板材表面的接触角呈现出下降的趋势；共聚物的降解速度和水接触角存在对应关系，水接触角的减小会增加共聚物的降解速度。
Researches and developments of functional biodegradable polymers which play a goodrole not only in the increasingly serious problems of resources and environment but also inthe development of new materials of the clinical medicine, biomedical and other fields havebecome a current research focus. In a variety of degradable polymers, Polymers based onpolycaprolactone (PCL) have been paid more attention owing to the characteristics ofexcellent biocompatibility, biodegradability, drug permeability and nontoxicity. Hydroycinnamic acid which derived from plants is a kind of photoreactive “plant monomer”. Thephotoreactive polyesters obtained from the two monomers by different forms of chemicalbond have the concentrated properties of both the two monomers, the weakness can beimproved and the advantages can be promoted. Regulation of such polyester performance canbe achieved through the control of their structure, composition. The regulation of theproperties of these kinds of polyesters can be achieved through the control of their structuresand compositions.
In this paper, PCL homo-polymers with different molecular weight were synthesized bya ring-opening polymerization method, and then series of PCL-co-P4HCA copolymers werealso synthesized via a thermal polycondensation method using PCL and4HCA monomers.The structures of the copolymers have been confirmed by FTIR and1H NMR. The results ofGPC showed that the molecular weights of PCL-co-P4HCA were between8.7×104-10.1×104g/mol, and the molecular weight distribution would much wider when the molecularweight was higher. PCL-co-P4HCA copolymers were photoreactive, and the absorption ofthe cinnamoyl group at306nm decreased rapidly and then decreased gradually withincreasing time of302nm UV irradiation. Moreover, PCL-co-P4HCA copolymers withhigher4HCA compositions showed greater photoreactivity rates and the decline degree after50min. PCL-co-P4HCA copolymers have fluorescence properties, the maximum emissionpeak intensity at450nm of these polymers decreased linearly with a decrease in4HCAcontent and the increase time of UV irradiation. The results of DSC and WXRD showedPCL-co-P4HCA copolymers were crystalline of PCL and P4HCA homo-polymers, thecrystallinity would decrease with a decrease of PCL composition. PCL-co-P4HCAcopolymers have excellent thermal stabilities which decrease regularly when irradiated withUV rays. The water contact angles of the PCL-co-P4HCA sheets increased with a decrease in4HCA content and the increase time of UV irradiation. The hydrolysis rate of thePCL-co-P4HCA sheets increased with an increase in4HCA content, and the rates ofhydrolysis were significantly higher under alkaline conditions than under neutral conditions.The degradation rates of the copolymers after UV irradiation were slightly slower due to the higher surface hydrophobicity.
Hyprebranched PCL-co-PDHCA copolymers were obtained by thermalmelt-polycondensation of PCL and AB2type DHCA monomer. The structures and thebranching degree were identified by1H NMR, and transesterification during thepolymerization might also occur from the results of FTIR and GPC. PCL-co-PDHCAcopolymers were photoreactive, and the crosslinking degree after75min UV irradiationwhich increased with an increase of DHCA composition might achieve about30%. Thefluorescence properties of PCL-co-PDHCA will be influenced by branching degree. Theemission intensity increased with increasing of the DHCA composition under the lowerbranching degree, a high branching degree will cause the fluorescent quenched and induce adecline of the emission intensity. The results of DSC and WXRD showed the crystallinity ofPCL-co-PDHCA copolymers reflected the PCL chain mainly, and the melt point andcrystallinity would decrease with an increase of DHCA composition. PCL-co-PDHCAcopolymers have excellent thermal stabilities which will influence by polymer component,branching degree and UV irradiation. The degradation rates of copolymers sheets would slowdown by increasing the PCL composition and UV irradiation.
Linear P4HCA, PCL-co-P4HCA and hyperbranched PDHCA, PCL-co-PDHCApolymers were obtained using anhydrous sodium phosphate as a catalyst. The structures ofthe polymers have been confirmed by FTIR and1H NMR. The reactivity of AB2type DHCAis higher than4HCA. The photocrosslinking degrees of hyperbranched polymers are higherthan the one of linear polymers after55min UV irradiation. However, the linear architectureis more prone to carry out the cis-trans isomerization, and the linear polymers have strongerfluorescence intensity. Hyperbranched architectures cause the better thermal stability of thepolymers due to the stronger π-π stacking. The result of WXRD and accelerated degradationtest showed the stronger crystalline of PCL-co-P4HCA lead to the slower degradation rate.
PECL-4ACA triblock copolymers were obtained from PECL synthesized byring-opening polymerization and4ACC. The results of DSC showed the copolymers werecrystalline, and the melting point increased with the increasing of the PCL chain composition.The thermal stability of the copolymers has been enhanced owing to the4ACA terminalgroups which restrain thermal decomposition of the aliphatic polyester PCL segment.PECL-4ACA copolymers display a reversible photosensitivity under302and254nm UVirradiation. PEG chains play a dominant role in the contact angle which express declinetendency as the introduction of4ACA terminal groups. The polymers which were muchhydrophilic had the faster degradation rate.
引文
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