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酰基氧化膦类光引发剂的绿色合成及应用研究

Green Synthesis and Application Study of Novel Photoinitiators of Acyl Phosphine

【作者】 王婷婷

【导师】 于青;

【作者基本信息】 山东科技大学 , 材料物理与化学, 2018, 硕士

【摘要】 酰基氧化膦是工业中用量较广的一类光引发剂。因具有良好的光引发性能,它广泛应用于涂料、清漆、3D打印、UV油墨印刷、牙科材料修复、食品包装等领域。近年来,酰基氧化膦的合成及应用成为LED光固化领域的热门课题。因此,本文的研究基于酰基氧化膦类引发剂开展。首先探讨了应用最多的酰基氧化膦——2,4,6-三甲基苯甲酰基二苯基氧化膦(2,4,6-trimethylbenzoyldipenylphosphine oxide,TPO)的合成工艺。通过探索本文首次成功得到了具有高活性、可循环使用性的催化剂V/MCM-41,获得了最佳反应条件。在该条件下,V/MCM-41氧化体系的TPO收率较原有体系提高10%。其次,以2-萘甲醛和二苯基氧化膦为原料设计并成功合成了一种新型酰基氧化膦类光引发剂——2-萘甲酰基二苯基氧化膦(2-naphthoyldipenylphosphine oxide,NPO)。采用NMR、MS和IR对其结构进行了确认。最后,对比了 NPO与TPO的光学性质、光引发性能和迁移率。结果表明:与TPO相比,新型光引发剂NPO的吸光波长明显红移且摩尔吸光系数高一个数量级;在引发三羟甲基丙烷三丙烯酸酯(trimethylolpropane triacrylate,TMPTA)聚合时,NPO表现出优于TPO的引发性能;在相同条件下,NPO固化体系中的引发剂迁移率明显低于TPO固化体系。因此,食品包装或齿科材料修复等领域NPO较TPO更具优势。

【Abstract】 Acyl phosphine is one of the most wildly used photoinitiators.Due to its" excellent trigger performance,it could be applied widely in the fields such as coating,varnish,3D printing,UV print dental material and food packaging.In recent years,the synthesis and application of acyl phosphine has become a hot topic in the field of LED light curing.Thus,the study in this thesis is based on acyl phosphine.Firstly,the synthesis method of mostly used acyl phosphine,2,4,6-trimethylbenzoyldipenylphosphine oxide(TPO)was discussed.The catalyst with high activity and reusability,V/MCM-41,was successfully obtained for the first time.Optimum conditions for the reaction were gained too.Under such conditions,the yield of TPO in V/MCM-41 system was 10%higher than the original one.Secondly,a new type of photoinitiator of acyl phosphine,2-naphthoyldipenylphosphine oxide(NPO),was successfully designed and synthesized using2-naphthalene formaldehyde and diphenylphosphineas raw materials.The structure of NPO was confirmed by NMR,MS and IR.Finally,the optical property,capability as photoinitiator and migration of NPO were compared with those of TPO.Results show that compared with TPO,the absorbance wavelength of the new photoinitiator NPO redshifted obviously and its molar absorption coefficient about an order of magnitude higher than that of TPO.In the photo-initiated polymerization of trimethylolpropane triacrylate(TMPTA),NPO exhibited better performance than TPO.In addition,the migration of photoinitiator in NPO cured system is much lower than the TPO ones.Therefore,NPO has more advantages than TPO in the field of food packaging or dental materials repair.

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