Preferential Orientation Effect of Polymers on Paracetamol Crystallization: Experiments and Modeling

被引:12
作者
Song, Yang [1 ]
Cai, Zhihui [1 ]
Li, Zhixian [1 ]
Guan, Guoqiang [1 ]
Jiang, Yanbin [1 ]
机构
[1] South China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
HETEROGENEOUS NUCLEATION; INDUCED HETERONUCLEATION; POLYMORPH SELECTION; AQUEOUS-SOLUTION; CRYSTALS; SURFACE; GROWTH; MECHANISM; TRANSIENT; INSIGHTS;
D O I
10.1021/acs.cgd.8b00346
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Crystallization is one of the most important unit operations in the quality control of pharmaceutical products. For this study, a polymer-induced heteronucleation method was selected to investigate the effect of nylon 66 (PA66), polyester (PET), and polypropylene (PP) films on the crystal growth of paracetamol by coupling experiments with modeling. The result of induction time indicated that the order of induced effect was PA66 > PET > PP > no template. X-ray photoelectron spectroscopy results indicated the different functional groups on the surface of films. The crystal habits and powder X-ray diffraction results indicated that preferential orientation along certain facets occurred for PA66 and PET, and the results of in situ Raman microscopy verified the different concentration trends near different films, which is consistent with the preferential orientation effect of films. The results of molecular simulation indicated that the difference in van der Waals and electrostatic interaction, as well as H-bond donor/acceptor on the polymer films, is the origin of the preferential orientation effect for paracetamol crystallization. The PP film modified with similar functional groups of PA66 on surfaces caused the same preferential orientation effect as PA66, which verified the functional-induced mechanism of the preferential orientation. This study could contribute to the investigation of the mechanism of polymer-induced heteronucleation and screen out the efficient templates.
引用
收藏
页码:4987 / 4997
页数:11
相关论文
共 35 条
[11]  
Harano K, 2012, NAT MATER, V11, P877, DOI [10.1038/NMAT3408, 10.1038/nmat3408]
[12]   Crystallization of acetaminophen on chitosan films blended with different acids [J].
Hsu, Hsinyun ;
Adigun, Oluwamayowa O. ;
Taylor, Lynne S. ;
Murad, Sohail ;
Harris, Michael T. .
CHEMICAL ENGINEERING SCIENCE, 2015, 126 :1-9
[13]   The use of polymer heteronuclei for crystalline polymorph selection [J].
Lang, MD ;
Grzesiak, AL ;
Matzger, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) :14834-14835
[14]   Crystal Polymorphism in Chemical Process Development [J].
Lee, Alfred Y. ;
Erdemir, Deniz ;
Myerson, Allan S. .
ANNUAL REVIEW OF CHEMICAL AND BIOMOLECULAR ENGINEERING, VOL 2, 2011, 2 :259-280
[15]   Controlling the selective and directional migration of hepatocytes by a complementary density gradient of glycosylated hyperbranched polymers and poly(ethylene glycol) molecules [J].
Liang, Su ;
Yu, Shan ;
Zhou, Ning ;
Deng, Jun ;
Gao, Changyou .
ACTA BIOMATERIALIA, 2017, 56 :161-170
[16]   Structural Correspondence of the Oriented Attachment Growth Mechanism of Crystals of the Pharmaceutical Dirithromycin [J].
Liang, Zuozhong ;
Wang, Yuan ;
Wang, Wei ;
Han, Xianglong ;
Chen, Jian-Feng ;
Xue, Chunyu ;
Zhao, Hong .
LANGMUIR, 2015, 31 (51) :13802-13812
[17]   Understanding the growth morphology of explosive crystals in solution: insights from solvent behavior at the crystal surface [J].
Liu, Yingzhe ;
Lai, Weipeng ;
Yu, Tao ;
Ma, Yiding ;
Kang, Ying ;
Ge, Zhongxue .
RSC ADVANCES, 2017, 7 (03) :1305-1312
[18]   Nonamorphism in Flufenamic Acid and a New Record for a Polymorphic Compound with Solved Structures [J].
Lopez-Mejias, Vilmali ;
Kampf, Jeff W. ;
Matzger, Adam J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (24) :9872-9875
[19]   On the Mechanism of Crystalline Polymorph Selection by Polymer Heteronuclei [J].
Lopez-Mejias, Vilmali ;
Knight, Jennifer L. ;
Brooks, Charles L., III ;
Matzger, Adam J. .
LANGMUIR, 2011, 27 (12) :7575-7579
[20]   Polymer-Induced Heteronucleation of Tolfenamic Acid: Structural Investigation of a Pentamorph [J].
Lopez-Mejias, Vilmali ;
Kampf, Jeff W. ;
Matzger, Adam J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (13) :4554-+