Synthesis and properties of cross-linkable polysiloxane via incorporating benzocyclobutene

High Performance Polymers

Volumn 26, Issue 4, 2014, Pages 463-469

  Yang, Junxiao ^a   Yang, Lu ^a   Cao, Ke ^a   Huang, Yawen ^a   Chang, Guanjun ^a   Zhu, Fanghua ^b  

^a SOUTHWEST UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b RESEARCH CENTER OF LASER FUSION   (China)

Author keywords

benzocyclobutene; cross linkable; Polysiloxane; thermal stability

Indexed keywords

BUTENES; DIFFERENTIAL SCANNING CALORIMETRY; HYDROSILYLATION; RESINS; SILANES; SYNTHESIS (CHEMICAL); THERMODYNAMIC STABILITY;

BENZOCYCLOBUTENE; CROSS-LINKABLE; HIGH TEMPERATURE PERFORMANCE; HYDROSILYLATION REACTION; INCORPORATION RATIO; ONSET DECOMPOSITION TEMPERATURES; PENDANT GROUPS; POLYSILOXANE;

SILICONES;

EID: 84901007868     PISSN: 09540083     EISSN: 13616412     Source Type: Journal    
DOI: 10.1177/0954008313518567     Document Type: Article

References (36)

1. Mark JE, Allcock HR, West R Inorganic polymers. Englewood Cliffs, NJ: Prentice Hall ; 1992: 141.
2. Dvornic PR, Gerov VV. Polymerization by hydrosilation. 1. Preparation of poly[(1,1,3,3-tetramethyldisiloxanyl)ethylene]. A preliminary report. Macromolecules. 1994 ; 27: 1068-1070
3. Dvornic PR, Gerov VV, Govedarica MN. Polymerization by hydrosilation. 2. Preparation and characterization of high molecular weight poly[(1,1,3,3- tetramethyldisiloxanyl)ethylene] from 1,3-dihydridotetramethyldisiloxane and 1,3-divinyltetramethyldisiloxane. Macromolecules. 1994 ; 27: 7575-7580
4. Mathias LJ, Lewis CM. Unexpectedly rapid hydrosilation polymerization of the diallyl derivative of bisphenol A and 2,6-diallylphenol. Macromolecules. 1993 ; 26: 4070-4071
5. Wu ZZ, Papandrea JP, Apple T, Leonard VI. Cross-linkable carbosilane polymers with imbedded disilacyclobutane rings derived by acyclic diene metathesis polymerization. Macromolecules. 2004 ; 37: 5257-5264
6. Birot M, Pillot JP, Dunogues J. Comprehensive chemistry of polycarbosilanes, polysilazanes, and polycarbosilazanes as precursors of ceramics. Chem Rev. 1995 ; 95: 1443-1477
7. Noll W Chemistry and technology of silicones. New York, NY: Academic Press ; 1968: 437-530.
8. Sakellariou G, Baskaran D, Hadjichristidis N, Mays JW. Well-defined poly(4-vinylbenzocyclobutene): synthesis by living anionic polymerization and characterization. Macromolecules. 2006 ; 39: 3525-3530
9. So YH, Hahn SF, Li YF, Reinhard MT. Styrene 4-vinylbenzocyclobutene copolymer for microelectronic applications. J Polym Sci Polym Chem. 2008 ; 46: 2799-2806
10. Muller WT, Ringsdorf H. Acetylene-substituted aromatic polyamides: curable systems. Macromolecules. 1990 ; 23: 2825-2829
11. Harkness BR, Tachikawa M. An examination of a styrenic thermoset formed by an α,ω 4-vinylphenyl functional diphenylsiloxane oligomer. Chem Mater. 1998 ; 10: 1706-1712
12. Li HY, Zhang JY, Xu RW, Yu DS. Direct synthesis and characterization of crosslinked polysiloxanes via anionic ring-opening copolymerization with octaisobutyl-polyhedral oligomeric silsesquioxane and octamethylcyclotetrasiloxane. J Appl Polym Sci. 2006 ; 102: 3848-3856
13. Mukbaniani O, Tatrishvili T, Titvinidze G, Patsatsia S. Synthesis of thermoreactive polysiloxanes with cyclic fragments in the side chain. J Appl Polym Sci. 2009 ; 114: 892-900
14. Bratcher MS, DeClue MS, Grunnet-Jepsen A, Wright D, Smith BR, Moerner WE, et al. Synthesis of bifunctional photorefractive polymers with net gain: design strategy amenable to combinatorial optimization. J Am Chem Soc. 1998 ; 120: 9680-9681
15. Belfield KD, Chinna C, Najjar O. Synthesis of novel polysiloxanes containing charge transporting and second-order nonlinear optical functionalities with atom economical constructs. Macromolecules. 1998 ; 31: 2918-2924
16. Zhang M, Wu YJ, Wu HY, Zhang QS, Xia YM. Synthesis and characterization of α,ω-bis(3-hydroxypropyl)-functionalized poly{dimethylsiloxane-co- methyl[3-(2-acetyl-acetoxy)]propylsiloxane}. J Appl Polym Sci. 2012 ; 125: 595-607
17. Zhu QZ, Feng SY, Zhang C. Synthesis and thermal properties of polyurethane-polysiloxane crosslinked polymer networks. J Appl Polym Sci. 2003 ; 90: 310-315
18. Zhan F, Cheng XE, Shi WF. Cationic UV curing behavior and thermal properties of oxetane-modified polysiloxane prepared from tetraethyl orthosilicate. J Appl Polym Sci. 2012 ; 123: 717-724
19. Dworak DP, Soucek MD. Synthesis of cycloaliphatic substituted silane monomers and polysiloxanes for photocuring. Macromolecules. 2004 ; 37: 9402-9417
20. Boutevin B, Guida-Pietrasanta F, Ratsimihety A. Synthesis of photocrosslinkable fluorinated polydimethylsiloxanes: direct introduction of acrylic pendant groups via hydrosilylation. J Polym Sci Polym Chem. 2003 ; 38: 3722-3728
21. Dworak DP, Soucek MD. Synthesis, characterization, and evaluation of amine-terminated cycloaliphatic-substituted polysiloxanes. Macro Chem Pysic. 2007 ; 208: 2502-2509
22. Li HY, Yu DS, Zhang JY. A novel and facile method for direct synthesis of cross-linked polysiloxanes by anionic ring-opening copolymerization with Ph12-POSS/D4/Ph8D4. Polymer. 2005 ; 46: 5317-5323
23. Ghosh A, Banerjee S, Komber H, Huabler L, Schneider K, Voit B. New semifluorinated siloxane-grafted copolyimides: synthesis and comparison with their linear analogs. Macro Mater Eng. 2011 ; 296: 391-400
24. Zou LJ, Anthamatten M. Synthesis and characterization of polyimide-polysiloxane segmented copolymers for fuel cell applications. J Polym Sci Polym Chem. 2007 ; 45: 3747-3758
25. Pei XL, Chen GF, Fang XZ. Synthesis and properties of poly(imide siloxane) block copolymers with different block lengths. J Appl Polym Sci. 2013 ; 129: 3718-3727
26. Drake K, Mukherjee I, Mirza K, Ji HF, Wei Y. Phenylethynyl and phenol end-capping studies of polybiphenyloxydiphenylsilanes for cross-linking and enhanced thermal stability. Macromolecules. 2011 ; 44: 4107-4115
27. Zuniga CA, Abdallah J, Haske W, Zhang YD, Coropceanu I, Barlow S, et al. Crosslinking using rapid thermal processing for the fabrication of efficient solution-processed phosphorescent organic light-emitting diodes. Adv Mater. 2013 ; 25: 1739-1744
28. Chakraborty R, Soucek MD. Mechanical and film properties of thermally curable polysiloxane. J Appl Polym Sci. 2010 ; 115: 358-369
29. Farona MF. Benzocyclobutenes in polymer chemistry. Prog Polym Sci. 1996 ; 21: 505-555
30. Yang JX, Huang YW, Cao K Polymerization. Gomes ADS, ed. 2012: pp. 201-222.
31. Volksen W, Miller RD, Dubois G. Low dielectric constant materials. Chem Rev. 2010 ; 110: 56-110
32. Zhao XY, Liu HJ. Review of polymer materials with low dielectric constant. Polym Int. 2010 ; 59: 597-606
33. Yang JX, Liu SC, Zhu FH, Huang YW, Li B, Zhang L. New polymers derived from 4-vinylsilylbenzocyclobutene monomer with good thermal stability, excellent film-forming property, and low-dielectric constant. J Polym Sci Polym Chem. 2011 ; 49: 381-391
34. Hahn S, Martin S, McKelvy L, Patrick D. Thermal polymerization of bis(benzocyclobutene) monomers containing.alpha.,beta.-disubstituted ethenes. Macromolecules. 1993 ; 26: 3870-3877
35. Zuo X, Yu R, Shi S, Feng Z, Li Z, Yang S, et al. Synthesis and characterization of photosensitive benzocyclobutene-functionalized siloxane thermosets. J Polym Sci Polym Chem. 2009 ; 47: 6246-6258
36. Yang J, Cheng Y, Xiao F. Synthesis, thermal and mechanical properties of benzocyclobutene-functionalized siloxane thermosets with different geometric structures. Eur Polym J. 2012 ; 48: 751-760