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
[1]   FT-IR and Raman spectroscopic methods for identification and quantitation of orthorhombic and monoclinic paracetamol in powder mixes [J].
Al-Zoubi, N ;
Koundourellis, JE ;
Malamataris, S .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2002, 29 (03) :459-467
[2]   The effect of tailor-made additives on crystal growth of methyl paraben: Experiments and modelling [J].
Cai, Zhihui ;
Liu, Yong ;
Song, Yang ;
Guan, Guoqiang ;
Jiang, Yanbin .
JOURNAL OF CRYSTAL GROWTH, 2017, 461 :1-9
[3]   Polymorphic control by heterogeneous nucleation - A new method for selecting crystalline substrates [J].
Chadwick, Keith ;
Myerson, Allan ;
Trout, Bernhardt .
CRYSTENGCOMM, 2011, 13 (22) :6625-6627
[4]   Regulating Nucleation Kinetics through Molecular Interactions at the Polymer-Solute Interface [J].
Curcio, Efrem ;
Lopez-Mejias, Vilmali ;
Di Profio, Gianluca ;
Fontananova, Enrica ;
Drioli, Enrico ;
Trout, Bernhardt L. ;
Myerson, Allan S. .
CRYSTAL GROWTH & DESIGN, 2014, 14 (02) :678-686
[5]   Crystal structures of drugs: Advances in determination, prediction and engineering [J].
Datta, S ;
Grant, DJW .
NATURE REVIEWS DRUG DISCOVERY, 2004, 3 (01) :42-57
[6]   Crystal Engineering: From Molecule to Crystal [J].
Desiraju, Gautain R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (27) :9952-9967
[7]   The role of prenucleation clusters in surface-induced calcium phosphate crystallization [J].
Dey, Archan ;
Bomans, Paul H. H. ;
Mueller, Frank A. ;
Will, Julia ;
Frederik, Peter M. ;
de With, Gijsbertus ;
Sommerdijk, Nico A. J. M. .
NATURE MATERIALS, 2010, 9 (12) :1010-1014
[8]   Surface Design for Controlled Crystallization: The Role of Surface Chemistry and Nanoscale Pores in Heterogeneous Nucleation [J].
Diao, Ying ;
Myerson, Allan S. ;
Hatton, T. Alan ;
Trout, Bernhardt L. .
LANGMUIR, 2011, 27 (09) :5324-5334
[9]   First-principles and direct design approaches for the control of pharmaceutical crystallization [J].
Fujiwara, M ;
Nagy, ZK ;
Chew, JW ;
Braatz, RD .
JOURNAL OF PROCESS CONTROL, 2005, 15 (05) :493-504
[10]   Selection of protein crystal forms facilitated by polymer-induced heteronucleation [J].
Grzesiak, Adam L. ;
Matzger, Adam J. .
CRYSTAL GROWTH & DESIGN, 2008, 8 (01) :347-350