Strong Microcapsules with Permeable Porous Shells Made through Phase Separation in Double Emulsions

Langmuir

Volumn 33, Issue 9, 2017, Pages 2402-2410

  Loiseau, Eve ^a   Niedermair, Fabian ^b   Albrecht, Gerhard ^b   Frey, Marion ^a   Hauser, Alina ^a   Rühs, Patrick A ^a   Studart, André R ^a  

^a ETH ZURICH   (Switzerland)

^b BASF SE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EMULSIFICATION; MECHANICAL PERMEABILITY; MICROSTRUCTURE; POROSITY; SEPARATION; SHELLS (STRUCTURES);

CONTROLLED PERMEABILITY; HIGH MECHANICAL STRENGTH; MECHANICALLY ROBUST; MECHANISM OF PHASE SEPARATION; MICRO-FLUIDIC DEVICES; ON-DEMAND RELEASE; POLYMER PARTICLES; SHELL PERMEABILITY;

PHASE SEPARATION;

EID: 85014750982     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/acs.langmuir.6b04408     Document Type: Article

References (49)

1. Mathiowitz, E.; Jacob, J. S.; Jong, Y. S.; Carino, G. P.; Chickering, D. E.; Chaturvedi, P.; Santos, C. A.; Vijayaraghavan, K.; Montgomery, S.; Bassett, M.; Morrell, C. Biologically erodable microspheres as potential oral drug delivery systems Nature 1997, 386 (6623) 410-414 10.1038/386410a0
2. Zhang, Y.; Riduan, S. N. Functional porous organic polymers for heterogeneous catalysis Chem. Soc. Rev. 2012, 41 (6) 2083-2094 10.1039/C1CS15227K
3. Arnal, P. M.; Comotti, M.; Schüth, F. High-Temperature-Stable Catalysts by Hollow Sphere Encapsulation Angew. Chem. 2006, 118 (48) 8404-8407 10.1002/ange.200603507
4. Yu, Q.; Tao, Y.; Huang, Y.; Lin, Z.; Zhuang, Y.; Ge, L.; Shen, Y.; Hong, M.; Xie, A. Preparation of Porous Polysulfone Microspheres and Their Application in Removal of Oil from Water Ind. Eng. Chem. Res. 2012, 51 (23) 8117-8122 10.1021/ie203028h
5. Fei, J. B.; Cui, Y.; Yan, X. H.; Qi, W.; Yang, Y.; Wang, K. W.; He, Q.; Li, J. B. Controlled Preparation of MnO2 Hierarchical Hollow Nanostructures and Their Application in Water Treatment Adv. Mater. 2008, 20 (3) 452-456 10.1002/adma.200701231
6. Maeda, S.; Nonaka, T.; Ogata, T.; Kurihara, S. Synthesis of macroreticular copolymer beads having various phenolic derivatives immobilized via different bond and their radical scavenging activity J. Appl. Polym. Sci. 2006, 102 (5) 4791-4800 10.1002/app.24194
7. Delaney, P.; Healy, R. M.; Hanrahan, J. P.; Gibson, L. T.; Wenger, J. C.; Morris, M. A.; Holmes, J. D. Porous silica spheres as indoor air pollutant scavengers J. Environ. Monit. 2010, 12 (12) 2244-2251 10.1039/c0em00226g
8. Cao, S.-W.; Zhu, Y.-J. Hierarchically Nanostructured α-Fe2O3 Hollow Spheres: Preparation, Growth Mechanism, Photocatalytic Property, and Application in Water Treatment J. Phys. Chem. C 2008, 112 (16) 6253-6257 10.1021/jp8000465
9. Gokmen, M.T.; Du Prez, F. E. Porous polymer particles-A comprehensive guide to synthesis, characterization, functionalization and applications Prog. Polym. Sci. 2012, 37, 365 10.1016/j.progpolymsci.2011.07.006
10. Caruso, F. Hollow Capsule Processing through Colloidal Templating and Self-Assembly Chem.-Eur. J. 2000, 6 (3) 413-419 10.1002/(SICI)1521-3765(20000204)6:3<413::AID-CHEM413>3.0.CO;2-9
11. Velev, O. D.; Furusawa, K.; Nagayama, K. Assembly of latex particles by using emulsion droplets as templates 0.1. Microstructured hollow spheres Langmuir 1996, 12 (10) 2374-2384 10.1021/la9506786
12. Dinsmore, A. D.; Hsu, M. F.; Nikolaides, M. G.; Marquez, M.; Bausch, A. R.; Weitz, D. A. Colloidosomes: Selectively permeable capsules composed of colloidal particles Science 2002, 298 (5595) 1006-1009 10.1126/science.1074868
13. Ma, Y. J.; Dong, W. F.; Hempenius, M. A.; Mohwald, H.; Vancso, G. J. Redox-controlled molecular permeability of composite-wall microcapsules Nat. Mater. 2006, 5 (9) 724-729 10.1038/nmat1716
14. Skirtach, A. G.; Dejugnat, C.; Braun, D.; Susha, A. S.; Rogach, A. L.; Parak, W. J.; Mohwald, H.; Sukhorukov, G. B. The role of metal nanoparticles in remote release of encapsulated materials Nano Lett. 2005, 5 (7) 1371-1377 10.1021/nl050693n
15. Sukhorukov, G. B.; Antipov, A. A.; Voigt, A.; Donath, E.; Mohwald, H. pH-controlled macromolecule encapsulation in and release from polyelectrolyte multilayer nanocapsules Macromol. Rapid Commun. 2001, 22 (1) 44-46 10.1002/1521-3927(20010101)22:1<44::AID-MARC44>3.0.CO;2-U
16. Caruso, F.; Trau, D.; Mohwald, H.; Renneberg, R. Enzyme encapsulation in layer-by-layer engineered polymer multilayer capsules Langmuir 2000, 16 (4) 1485-1488 10.1021/la991161n
17. Fery, A.; Weinkamer, R. Mechanical properties of micro- and nanocapsules: Single-capsule measurements Polymer 2007, 48 (25) 7221-7235 10.1016/j.polymer.2007.07.050
18. Sukhorukov, G.; Fery, A.; Mohwald, H. Intelligent micro- and nanocapsules Prog. Polym. Sci. 2005, 30 (8-9) 885-897 10.1016/j.progpolymsci.2005.06.008
19. Li, M.; Harbron, R. L.; Weaver, J. V. M.; Binks, B. P.; Mann, S. Electrostatically gated membrane permeability in inorganic protocells Nat. Chem. 2013, 5 (6) 529-536 10.1038/nchem.1644
20. Rossier-Miranda, F. J.; Schroën, C. G. P. H.; Boom, R. M. Colloidosomes: Versatile microcapsules in perspective Colloids Surf., A 2009, 343 (1-3) 43-49 10.1016/j.colsurfa.2009.01.027
21. He, X.; Ge, X.; Liu, H.; Wang, M.; Zhang, Z. Synthesis of Cagelike Polymer Microspheres with Hollow Core/Porous Shell Structures by Self-Assembly of Latex Particles at the Emulsion Droplet Interface Chem. Mater. 2005, 17 (24) 5891-5892 10.1021/cm051694j
22. Shiomi, T.; Tsunoda, T.; Kawai, A.; Mizukami, F.; Sakaguchi, K. Formation of cage-like hollow spherical silica via a mesoporous structure by calcination of lysozyme-silica hybrid particles Chem. Commun. 2007, 42, 4404-4406 10.1039/b709534a
23. Zhao, B.; Collinson, M. M. Hollow Silica Capsules with Well-Defined Asymmetric Windows in the Shell Langmuir 2012, 28 (19) 7492-7497 10.1021/la301560r
24. Chen, P. W.; Brignoli, J.; Studart, A. R. Mechanics of thick-shell microcapsules made by microfluidics Polymer 2014, 55 (26) 6837-6843 10.1016/j.polymer.2014.10.060
25. Chen, P. W.; Erb, R. M.; Studart, A. R. Designer Polymer-Based Microcapsules Made Using Microfluidics Langmuir 2012, 28 (1) 144-152 10.1021/la203088u
26. Loiseau, E.; de Boiry, A. Q.; Niedermair, F.; Albrecht, G.; Ruhs, P. A.; Studart, A. R. Explosive Raspberries: Controlled Magnetically Triggered Bursting of Microcapsules Adv. Funct. Mater. 2016, 26 (22) 4007-4015 10.1002/adfm.201504656
27. Sander, J. S.; Studart, A. R. Multiwalled functional colloidosomes made small and in large quantities via bulk emulsification Soft Matter 2014, 10 (1) 60-68 10.1039/C3SM51900G
28. Sander, J. S.; Studart, A. R. Nanoparticle-Filled Complex Colloidosomes for Tunable Cargo Release Langmuir 2013, 29 (49) 15168-15173 10.1021/la402901c
29. Sander, J. S.; Studart, A. R. Monodisperse Functional Colloidosomes with Tailored Nanoparticle Shells Langmuir 2011, 27 (7) 3301-3307 10.1021/la1035344
30. Lee, D.; Weitz, D. A. Double emulsion-templated nanoparticle colloidosomes with selective permeability Adv. Mater. 2008, 20 (18) 3498-3503 10.1002/adma.200800918
31. Sander, J. S.; Steinacher, M.; Loiseau, E.; Demirors, A. F.; Zanini, M.; Isa, L.; Studart, A. R. Robust Microcompartments with Hydrophobically Gated Shells Langmuir 2015, 31 (25) 6965-6970 10.1021/acs.langmuir.5b00732
32. Beneš, M. J.; Horák, D.; Svec, F. Methacrylate-based chromatographic media J. Sep. Sci. 2005, 28 (15) 1855-1875 10.1002/jssc.200500186
33. Svec, F.; Hradil, J.; Coupek, J.; Kalal, J. Reactive Polymers. 1. Macroporous Methacrylate Copolymers Containing Epoxy Groups Angew. Makromol. Chem. 1975, 48 (NOV) 135-143 10.1002/apmc.1975.050480108
34. Dusek, K. Inhomogeneities Induced by Crosslinking in the Course of Crosslinking Copolymerization. In Polymer Networks; Chompff, A. J.; Newman, S., Eds.; Springer: New York, 1971; pp 245-260.
35. Okay, O. Macroporous copolymer networks Prog. Polym. Sci. 2000, 25 (6) 711-779 10.1016/S0079-6700(00)00015-0
36. Horák, D.; Pelzbauer, Z.; Bleha, M.; Ilavský, M.; Švec, F.; Kálal, J. Reactive polymers. XXXII. Effect of composition of polymerization feed on morphology and some physical properties of macroporous suspension copolymers glycidyl methacrylate-ethylene dimethacrylate J. Appl. Polym. Sci. 1981, 26 (2) 411-421 10.1002/app.1981.070260203
37. Horák, D.; Pelzbauer, Z.; Ŝvec, F.; Kálal, J. Reactive polymers. XXXIII. The influence of the suspension stabilizer on the morphology of a suspension polymer J. Appl. Polym. Sci. 1981, 26 (10) 3205-3211 10.1002/app.1981.070261002
38. Horák, D.; Švec, F.; Bleha, M.; Kálal, J. Reactive polymers, XXXV. The effect of polymerization conditions on the specific surface area of macroporous copolymers from glycidylmethacrylate-ethylenedimethacrylate Angew. Makromol. Chem. 1981, 95 (1) 109-115 10.1002/apmc.1981.050950108
39. Horák, D.; Švec, F.; Ilavský, M.; Bleha, M.; Baldrián, J.; Kálal, J. Reactive polymers, XXXVI. The effect of polymerization conditions on the porosity and mechanical properties of macroporous suspension copolymers from glycidylmethacrylate-ethylenedimethacrylate Angew. Makromol. Chem. 1981, 95 (1) 117-127 10.1002/apmc.1981.050950109
40. Horák, D.; Švec, F.; Ribeiro, C. M. A.; Kálal, J. Reactive polymers, XXIX. The effect of components on the rate of polymerization in model mixtures containing glycidylmethacrylate and ethylenedimethacrylate Angew. Makromol. Chem. 1980, 87 (1) 127-136 10.1002/apmc.1980.050870109
41. Nam, J.-O.; Kim, J.; Jin, S. H.; Chung, Y.-M.; Lee, C.-S. Microfluidic preparation of a highly active and stable catalyst by high performance of encapsulation of polyvinylpyrrolidone (PVP)-Pt nanoparticles in microcapsules J. Colloid Interface Sci. 2016, 464, 246-253 10.1016/j.jcis.2015.11.037
42. Kim, B.; Jeon, T. Y.; Oh, Y.-K.; Kim, S.-H. Microfluidic Production of Semipermeable Microcapsules by Polymerization-Induced Phase Separation Langmuir 2015, 31 (22) 6027-6034 10.1021/acs.langmuir.5b01129
43. Utada, A. S.; Lorenceau, E.; Link, D. R.; Kaplan, P. D.; Stone, H. A.; Weitz, D. A. Monodisperse double emulsions generated from a microcapillary device Science 2005, 308 (5721) 537-541 10.1126/science.1109164
44. Chen, P. W.; Cadisch, G.; Studart, A. R. Encapsulation of Aliphatic Amines Using Microfluidics Langmuir 2014, 30 (9) 2346-2350 10.1021/la500037d
45. Dubinsky, S.; Zhang, H.; Nie, Z.; Gourevich, I.; Voicu, D.; Deetz, M.; Kumacheva, E. Microfluidic Synthesis of Macroporous Copolymer Particles Macromolecules 2008, 41 (10) 3555-3561 10.1021/ma800300d
46. Kaufmann, T.; Gokmen, M. T.; Wendeln, C.; Schneiders, M.; Rinnen, S.; Arlinghaus, H. F.; Bon, S. A. F.; Du Prez, F. E.; Ravoo, B. J. Sandwich" Microcontact Printing as a Mild Route Towards Monodisperse Janus Particles with Tailored Bifunctionality Adv. Mater. 2011, 23 (1) 79-83 10.1002/adma.201003564
47. Keller, M.; Sottos, N. Mechanical Properties of Microcapsules Used in a Self-Healing Polymer Exp. Mech. 2006, 46 (6) 725-733 10.1007/s11340-006-9659-3
48. Dubinsky, S.; Park, J. I.; Gourevich, I.; Chan, C.; Deetz, M.; Kumacheva, E. Toward Controlling the Surface Morphology of Macroporous Copolymer Particles Macromolecules 2009, 42 (6) 1990-1994 10.1021/ma802813v
49. Zeng, W.; Du, Y.; Xue, Y.; Frisch, H. L. Solubility Parameters. In Physical Properties of Polymers Handbook; Mark, J., Ed.; Springer: New York, 2007; pp 289-303.