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首页> 外文期刊>Acta biomaterialia >Poly(ε-caprolactone)-based copolymers bearing pendant cyclic ketals and reactive acrylates for the fabrication of photocrosslinked elastomers
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Poly(ε-caprolactone)-based copolymers bearing pendant cyclic ketals and reactive acrylates for the fabrication of photocrosslinked elastomers

机译：带有侧基缩酮和反应性丙烯酸酯的聚（ε-己内酯）基共聚物，用于制造光交联的弹性体

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Block copolymers of poly(ethylene glycol) and poly(ε-caprolactone) (PCL) with chemically addressable functional groups were synthesized and characterized. Ring-opening polymerization of ε-caprolactone (CL) and 1,4,8-trioxaspiro-[4,6]-9-undecanone (TSU) using α-methoxy, ω-hydroxyl poly(ethylene glycol) as the initiator afforded a copolymer with cyclic ketals being randomly distributed in the hydrophobic PCL block. At an initiator/catalyst molar ratio of 10/1 and a TSU/CL weight ratio of 1/4, a ketal-carrying copolymer (ECT2-CK) with Mn of 52 kDa and a ketal content of 15 mol.% was obtained. Quantitative side-chain deacetalization revealed the reactive ketones without noticeable polymer degradation. In our study, 10 mol.% of cyclic ketals were deprotected and the ketone-containing copolymer was designated as ECT2-CO. Reaction of ECT2-CO with 2-(2-(aminooxy)acetoxy)-ethyl acrylate gave rise to an acrylated product (ECT2-AC) containing an estimated 3-5 acrylate groups per chain. UV-initiated radical polymerization of ECT2-AC in dichloromethane resulted in a crosslinked network (xECT2-AC). Thermal and morphological analyses employing differential scanning calorimetry and atomic force microscopy operated in PeakForce Tapping mode revealed the semicrystalline nature of the network, which contained stiff crystalline lamellae dispersed in a softer amorphous interstitial. Macroscopic and nanoscale mechanical characterizations showed that ECT2-CK exhibited a significantly lower modulus than PCL of a similar molecular weight. Whereas ECT2-CK undergoes a plastic deformation with a distinct yield point and a cold-drawing region, xECT2-AC exhibits a compliant, elastomeric deformation with a Young's modulus of 0.5 ± 0.1 MPa at 37 C. When properly processed, the crosslinked network exhibited shape-memory behaviors, with shape fixity and shape recovery values close to 1 and a shape recovery time of less than 4 s at 37 C. In vitro studies showed that xECT2-AC films did not induce any cytotoxic effects on the cultured mesenchymal stem cells. The crosslinkable polyester copolymers can be potentially used as tissue engineering scaffolds and minimally invasive medical devices.
机译：合成并表征了具有化学可寻址官能团的聚乙二醇和聚ε-己内酯（PCL）的嵌段共聚物。使用α-甲氧基，ω-羟基聚乙二醇作为引发剂，ε-己内酯（CL）和1,4,8-三氧四环-[4,6] -9-十一烷酮（TSU）的开环聚合得到环状缩酮的共聚物随机分布在疏水PCL嵌段中。在引发剂/催化剂的摩尔比为10/1且TSU / CL的重量比为1/4的情况下，获得了具有52kDa的Mn和15mol。％的缩酮含量的缩酮负载共聚物（ECT2-CK）。定量的侧链脱缩醛反应显示出反应性酮，没有明显的聚合物降解。在我们的研究中，对10摩尔％的环状缩酮进行了脱保护，将含酮的共聚物命名为ECT2-CO。 ECT2-CO与丙烯酸2-（2-（氨基氧基）乙酰氧基）-乙酯的反应生成丙烯酸酯化的产物（ECT2-AC），每链估计有3-5个丙烯酸酯基。 UV-引发的ECT2-AC在二氯甲烷中的自由基聚合反应产生了交联网络（xECT2-AC）。使用差示扫描量热法和原子力显微镜在PeakForce Tapping模式下进行的热学和形态学分析揭示了网络的半晶体性质，该网络包含分散在较软的非晶质间隙中的硬质晶体薄片。宏观和纳米尺度的机械表征表明，ECT2-CK的模量明显低于分子量相似的PCL。 ECT2-CK经历具有明显屈服点和冷拔区域的塑性变形，而xECT2-AC在37°C时表现出柔顺的弹性变形，杨氏模量为0.5±0.1 MPa。经过适当处理，交联网络呈现出形状记忆行为，形状固定性和形状恢复值接近1，并且在37 C下的形状恢复时间小于4 s。体外研究表明，xECT2-AC膜对培养的间充质干细胞没有任何细胞毒性作用。可交联的聚酯共聚物可以潜在地用作组织工程支架和微创医疗设备。

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