Abstract
Polymeric microcapsules (MCs) filled with catalyst can be controlled to release the catalyst to initiate the polymerization reaction. In the present work, poly(urea–formaldehyde) (PUF) MCs filled with DBTDL (PUF/DBTDL MCs) were prepared using urea (U) and formaldehyde (F) as the wall shell materials by in situ polymerization. The U–F resins could easily polymerize in the presence of the core material DBTDL to produce PUF polymers, then they deposited on the surface of the DBTDL droplets, forming PUF/DBTDL MCs. The decomposition temperature (T d) at 5 % weight loss of PUF/DBTDL MCs was about 245 °C. The application of PUF/DBTDL MCs to cyanate ester resins preliminarily showed the reaction control capability of the MCs due to the slow release of DBTDL through the wall shell.
Similar content being viewed by others
References
Omrani A, Ghaemy M, Rostami AA (2009) Thermosetting polymers from epoxy resin and a Nickel catalyst of diethylenetriamine. J Therm Anal Calorim 98:477–483
You ZW, Bi XP, Jeffries EM, Wang YD (2012) A biocompatible, metal-free catalyst and its application in microwave-assisted synthesis of functional polyesters. Polym Chem 3:384–389
Li WF, Liang GZ, Xin WL (2004) Triazine reaction of cyanate ester resin systems catalyzed by organic tin compound: kinetics and mechanism. Polym Int 53:869–876
Dai SK, Zhuo DX, Gu AJ, Liang GZ, Yuan L (2011) A novel hybrid catalyst system and its effects on the curing, thermal, and dielectric properties of cyanate ester. Polym Eng Sci 51:2236–2244
Pengjam W, Saengfak B, Ekgasit S, Chantarasiri N (2012) Copper–amine complexes as new catalysts for rigid polyurethane foam preparations. J Appl Polym Sci 123:3520–3526
Burel F, Feldman A, Bunel C (2005) Hydrogenated hydroxy-functionalized polyisoprene (H-HTPI) and isocyanurate of isophorone diisocyanates (I-IPDI): reaction kinetics study using FTIR spectroscopy. Polymer 46:15–25
Xu JJ, Song R, Wu Q, Yu YZ (2001) Novel dibutyltin oxide-tributyl phosphate condensate as accelerator for the curing of the epoxy resin/4,4′-diamino diphenyl sulfone system. I. Chemical reactions and properties of the cured resin. J Appl Polym Sci 80:1229–1236
Ichiura H, Morikawa M, Fujiwara K (2005) Preparation of microcapsules that produce color in response to humidity for use in intelligent functional paper. J Mater Sci 40:1987–1991
Cejková J, Hanus J, Stepánek F (2010) Investigation of internal microstructure and thermo-responsive properties of composite PNIPAM/silica microcapsules. J Colloid Interf Sci 346:324–330
Fransaer J, Celis JP, Roos JR (1992) Electro-osmophoresis of a charged permeable microcapsule with thin double layer. J Colloid Interf Sci 151:26–40
Skirtach AG, Karageorgiev P, Bédard MF, Sukhorukov GB, Möhwald H (2008) Reversibly permeable nanomembranes of polymeric microcapsules. J Am Chem Soc 130:11572–11573
Pavlov AM, Sapelkin AV, Huang XY, P’ng KM, Bushby AJ, Sukhorukov GB, Skirtach AG (2011) Neuron cells uptake of polymeric microcapsules and subsequent intracellular release. Macromol Biosci 11:848–854
Lensen D, Gelderblom EC, Vriezema DM, Marmottant P, Verdonschot N, Versluis M, de Jong N, van Hest JCM (2011) Biodegradable polymeric microcapsules for selective ultrasound-triggered drug release. Soft Matter 7:5417–5422
Deyrai Y, Zydowicz N, Cassagnau P (2004) Polymer crosslinking controlled by release of catalyst encapsulated in polycarbonate micro-spheres. Polymer 45:6123–6131
Vallance MA, Evans TL, Kelly JM (1988) Composition and method for controlling polymerization rate of cyclic polycarbonate oligomer with encapsulated catalyst. US Patent 4755588
Kim WG (2009) Cure properties of self-extinguishing epoxy resin systems with microencapsulated latent catalysts for halogen-free semiconductor packaging materials. J Appl Polym Sci 113:408–417
Cho SH, Magnus Andersson H, White SR, Sottos NR, Braun PV (2006) Polydimethylsiloxane-based self-healing materials. Adv Mater 18:997–1000
Yuan L, Liang GZ, Xie JQ, Li L, Guo J (2006) Preparation and characterization of poly(urea–formaldehyde) microcapsules filled with epoxy resins. Polymer 47:5338–5349
Mookhoek SD, Blaiszik BJ, Fischer HR, Sottos NR, White SR, van der Zwaag S (2008) Peripherally decorated binary microcapsules containing two liquids. J Mater Chem 18:5390–5394
Niu XW, Sun YM, Ding SN, Chen CC, Song B, Xu HB, Qi ZJ, Qi Q (2012) Synthesis of enhanced urea-formaldehyde resin microcapsules doped with nanotitania. J Appl Polym Sci 124:248–256
Guo HL, Zhao XP, Wang JP (2005) Synthesis of functional microcapsules containing suspensions responsive to electric fields. J Colloid Interf Sci 284:646–651
Sun G, Zhang Z (2002) Mechanical strength of microcapsules made of different wall materials. Int J Pharm 242:307–311
Park SJ, Shin YS, Lee JR (2001) Preparation and characterization of microcapsules containing lemon oil. J Colloid Interf Sci 241:502–508
Torry SA, Campbell A, Cunliffe AV, Tod DA (2006) Kinetic analysis of organosilane hydrolysis and condensation. Int J Adhes Adhes 26:40–49
Christianson Peep, Pehk Tõnis, Siimer Kadri (2006) Structure formation in urea-formaldehyde resin synthesis. Proc Estonian Acad Sci Chem 55:212–225
Camino G, Operti L, Trossarelli L (1983) Mechanism of thermal degradation of urea-formaldehyde polycondensates. Polym Degrad Stabil 5:161–172
Piver WT (1973) Organotin compounds: industrial applications and biological investigation. Environ Health Perspect 4:61–79
Bryant YG (1999) Melt spun fibers containing microencapsulated phase change material. ASME BED 44:225–234
Nair CPR, Mathew D, Ninan KN (2001) Cyanate ester resins, recent developments. Adv Polym Sci 155:1–99
Liu J, Ding ND, Xu RF, He QH, Shen J, Hu BX (2011) Cyanate ester resin modified by hydroxyl-terminated polybutadiene: morphology, thermal, and mechanical properties. Polym Eng Sci 51:1404–1408
Acknowledgments
We thank “Jiangsu Government Scholarship for Overseas Studies” (2011–2012), National Natural Science Foundation of China (50903058 and 51273135), Scientific Research & Innovation Project of Graduate Students in Colleges and Universities of Jiangsu Province (CXLX12_0802) and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD). SN acknowledges support from the Gill Composites Center.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yuan, L., Chen, F., Gu, A. et al. Synthesis of poly(urea–formaldehyde) encapsulated dibutyltin dilaurate through the self-catalysis of core materials. Polym. Bull. 71, 261–273 (2014). https://doi.org/10.1007/s00289-013-1059-0
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-013-1059-0