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Controllable Fragrance Release Mediated by the Spontaneous Formation of Hydrogen Bonding with POSS-Thiourea Derivatives
CCS Chemistry ( IF 9.4 ) Pub Date : 2020/5/12 , DOI: 10.31635/ccschem.020.202000166
Chenwei Xue 1 , Ming Liu 1 , Zhi-Ang Zhang 1 , Jianwei Han 1 , Chengyun Wang 1 , Limin Wang 1 , Zuobing Xiao 2 , Wei-Hong Zhu 1
Affiliation  

The purpose of achieving the long-lasting fragrance perception leads to nanocarrier-based profragrances in perfume applications. Herein, we report a family of novel profragrance systems based on polyhedral oligomeric silsesquioxane (POSS) derivatized thioureas (POSS thioureas) that enable linkage of volatile carbonyl fragrances with the spontaneous formation of fragile hydrogen bonds. This profragrance platform addresses the dilemma of the volatile nature of aroma-materials on the one hand, and the desired long-lasting effects on the other. Their releasing performance as profragrances is investigated by headspace solid-phase microextraction (SPME) in combination with gas chromatography (GC) analysis under water as the external humidity stimulus, indicating that the fragrance concentration released from the POSS–thiourea-based profragrance is up to four times higher than the neat reference of the corresponding perfume aldehydes. Furthermore, deposition of the novel profragrance system onto wallpaper results in excellent retentive capacity for volatile aldehydes. Given the low essential toxicity, the POSS–thiourea system has been demonstrated as a suitable profragrance for practical application to perfume delivery.

中文翻译:

POSS-硫脲衍生物自发形成氢键介导的可控制的香料释放

实现持久香气感知的目的导致香水应用中基于纳米载体的香气。在此,我们报告了一个基于多面体低聚倍半硅氧烷(POSS)衍生的硫脲(POSS硫脲)的新型香精系统系列,该体系能够使挥发性羰基香料与脆弱的氢键自发形成连接。这种香气平台一方面解决了香气材料易挥发性质的难题,另一方面解决了所需的持久效果。通过顶空固相微萃取(SPME)结合气相色谱(GC)分析在水作为外部湿度刺激下研究了它们作为香精的释放性能,这表明从基于POSS-硫脲的香精中释放的香精浓度比相应的香精醛的纯净基准高出四倍。此外,将新颖的香精系统沉积到墙纸上可产生对挥发性醛的出色保留能力。由于基本毒性低,已证明POSS-硫脲系统可作为香料在实际应用中的合适香料。
更新日期:2020-12-18
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