Advanced search
Publication Cover
Journal of Macromolecular Science: Part A - Chemistry Volume 28, 1991 - Issue 11-12
Journal homepage
116
Views
63
CrossRef citations to date
0
Altmetric
Original Articles

Benzocyclobutenes: A New Class of High Performance Polymers

R. A. Kirchhoff Central Research, Materials Science & Development Laboratory The Dow Chemical Company, Midland, Michigan, 48674
,
C. J. Carriere Central Research, Materials Science & Development Laboratory The Dow Chemical Company, Midland, Michigan, 48674
,
K. J. Bruza Central Research, Materials Science & Development Laboratory The Dow Chemical Company, Midland, Michigan, 48674
,
N. G. Rondan Central Research, Materials Science & Development Laboratory The Dow Chemical Company, Midland, Michigan, 48674
&
R. L. Sammler Central Research, Materials Science & Development Laboratory The Dow Chemical Company, Midland, Michigan, 48674
Pages 1079-1113 | Published online: 23 Oct 2006

Citations (63)

Keep up to date with the latest research on this topic with citation updates for this article.

Subscribe to citation updates

Read on this site (1)

M. L. Jenkins, R. H. Dauskardt & J. C. Bravman. (2004) Important factors for silane adhesion promoter efficacy: surface coverage, functionality and chain length. Journal of Adhesion Science and Technology 18:13, pages 1497-1516.
Read now

Articles from other publishers (62)

Fengping Liu, Jing Sun & Qiang Fang. (2022) Fluorinated Benzocyclobutene-Based Low- k Polymer at High Frequency . ACS Applied Polymer Materials 4:2, pages 842-848.
Crossref
Jiaren Hou, Jing Sun & Qiang Fang. (2022) A fluorinated low dielectric polymer at high frequency derived from allylphenol and benzocyclobutene by a facile route. European Polymer Journal 163, pages 110943.
Crossref
Yudi Feng, Ke Jin, Jia Guo & Changchun Wang. (2021) All-carbocycle hydrocarbon thermosets with high thermal stability and robust mechanical strength for low- k interlayer dielectrics . Polymer Chemistry 12:33, pages 4812-4821.
Crossref
Ke Jin, Qiangsheng Sun, Yudi Feng, Jia Guo & Changchun Wang. (2021) High-performance polymers adapted to facile melt processing through structure design of benzocyclobutene-containing precursors. European Polymer Journal 151, pages 110445.
Crossref
Fengping Liu, Xingrong Chen, Jiaren Hou, Jing Sun & Qiang Fang. (2020) A Fluorinated Thermocrosslinkable Organosiloxane: A New Low ‐k Material at High Frequency with Low Water Uptake . Macromolecular Rapid Communications 42:5, pages 2000600.
Crossref
Rajour Tanyi Ako, Aditi Upadhyay, Withawat Withayachumnankul, Madhu Bhaskaran & Sharath Sriram. (2019) Dielectrics for Terahertz Metasurfaces: Material Selection and Fabrication Techniques. Advanced Optical Materials 8:3, pages 1900750.
Crossref
Xianfeng Que, Zhiming Qiu & Yurong Yan. (2019) Synthesis and properties of benzocyclobutene-terminated imide-containing cyano group. High Performance Polymers 31:9-10, pages 1062-1074.
Crossref
Xuelian Wei, Huan Hu, Xian Li, Qiang Yin, Li Fan, Yawen Huang & Junxiao Yang. (2019) Materials containing benzocyclobutene units with low dielectric constant and good thermostability prepared from star-shaped molecules. Journal of Applied Polymer Science 136:18, pages 47458.
Crossref
Xingrong Chen, Linxuan Fang, Xiaoyao Chen, Junfeng Zhou, Jiajia Wang, Jing Sun & Qiang Fang. (2018) A Low-Dielectric Polymer Derived from a Biorenewable Phenol (Eugenol). ACS Sustainable Chemistry & Engineering 6:10, pages 13518-13523.
Crossref
Xianfeng Que, Yurong Yan & Zhiming Qiu. (2018) Synthesis and characterization of benzocyclobutene-terminated imides with high organosolubility. European Polymer Journal 103, pages 410-420.
Crossref
Lingqiang Kong, Tianke Qi, Zhidong Ren, Yunxia Jin, Yan Li, Yuanrong Cheng & Fei Xiao. (2016) High-performance intrinsic low-k polymer via the synergistic effect of its three units: adamantyl, perfluorocyclobutylidene and benzocyclobutene. RSC Advances 6:73, pages 68560-68567.
Crossref
Lingqiang Kong, Yuanrong Cheng, Yunxia Jin, Zhidong Ren, Yan Li & Fei Xiao. (2015) Adamantyl-based benzocyclobutene low-k polymers with good physical properties and excellent planarity. Journal of Materials Chemistry C 3:14, pages 3364-3370.
Crossref
Jun Yang, Yuanrong Cheng, Yunxia Jin & Fei Xiao. (2013) Synthesis and properties of novel benzocyclobutene-functionalized siloxane thermosets. Polymer International 62:12, pages 1684-1691.
Crossref
Jun Yang, Yuanrong Cheng, Yunxia Jin, Dunying Deng & Fei Xiao. (2013) Synthesis and characterization of organo-soluble and photosensitive benzocyclobutene-terminated imides. European Polymer Journal 49:6, pages 1642-1653.
Crossref
Jun Yang, Yuanrong Cheng & Fei Xiao. (2012) Synthesis, thermal and mechanical properties of benzocyclobutene-functionalized siloxane thermosets with different geometric structures. European Polymer Journal 48:4, pages 751-760.
Crossref
Jun Yang, Yunxia Jin, Yuanrong Cheng & Fei Xiao. (2011) Synthesis, properties of novel benzocyclobutene-functionalized siloxane thermosets. Synthesis, properties of novel benzocyclobutene-functionalized siloxane thermosets.
Jun Yang, Mingfei Sun, Yuanrong Cheng & Fei Xiao. (2011) Study of benzocyclobutene-functionalized siloxane thermoset with a cyclic structure. Study of benzocyclobutene-functionalized siloxane thermoset with a cyclic structure.
Xiaobiao Zuo, Ruilian Yu, Song Shi, Zhihai Feng, Zhongping Li, Shiyong Yang & Lin Fan. (2009) Synthesis and characterization of photosensitive benzocyclobutene-functionalized siloxane thermosets. Journal of Polymer Science Part A: Polymer Chemistry 47:22, pages 6246-6258.
Crossref
Xiaobiao Zuo, Xiaojuan Zhao, Biao Liu, Shiyong Yang & Lin Fan. (2009) Synthesis and properties of fluorinated bis‐benzocyclobutene‐terminated arylene ether monomers. Journal of Applied Polymer Science 112:5, pages 2781-2791.
Crossref
Xiaobiao Zuo, Jiansheng Chen, Xiaojuan Zhao, Shiyong Yang & Lin Fan. (2008) Synthesis and characterization of siloxane resins derived from silphenylene‐siloxane copolymers bearing benzocyclobutene pendant groups. Journal of Polymer Science Part A: Polymer Chemistry 46:23, pages 7868-7881.
Crossref
Ying-Hung So, Pamela Foster, Jang-Hi Im, Philip Garrou, Jack Hetzner, Edmund Stark & Kayla Baranek. (2006) Divinylsiloxane-bisbenzocyclobutene-based polymer modified with polystyrene-polybutadiene-polystyrene triblock copolymers. Journal of Polymer Science Part A: Polymer Chemistry 44:5, pages 1591-1599.
Crossref
Yingqiang Zhang, Jianying Gao, Xuening Shen & Farong Huang. (2005) The preparation, characterization, and cure reactions of new bisbenzocyclobutene‐terminated aromatic imides. Journal of Applied Polymer Science 99:4, pages 1705-1719.
Crossref
Yingqiang Zhang, Xuening Shen & Farong Huang. (2005) Thermal stability and degradation products analysis of benzocyclobutene-terminated imide polymers. Thermochimica Acta 430:1-2, pages 15-22.
Crossref
D.-Q. Yang, S. Poulin, L. Martinu, J.E. Klemberg-Sapieha, O. Zabeida & E. Sacher. (2005) Microscale chemical and electrostatic surface patterning of Dow Cyclotene by N2 plasma. Applied Surface Science 242:3-4, pages 419-427.
Crossref
I. Christiaens, G. Roelkens, Kurt De Mesel, D. Van Thourhout & R. Baets. (2005) Thin-film devices fabricated with benzocyclobutene adhesive wafer bonding. Journal of Lightwave Technology 23:2, pages 517-523.
Crossref
S.-Y. Cho, S.-W. Seo, N.M. Jokerst & M.A. Brooke. (2004) Board-Level Optical Interconnection and Signal Distribution Using Embedded Thin-Film Optoelectronic Devices. Journal of Lightwave Technology 22:9, pages 2111-2118.
Crossref
E.N. Glytsis, N.M. Jokerst, R.A. Villalaz, Sang-Yeon Cho, Shun-Der Wu, Zhaoran Huang, M.A. Brooke & T.K. Gaylord. (2003) Substrate-embedded and flip-chip-bonded photodetector polymer-based optical interconnects: analysis, design, and performance. Journal of Lightwave Technology 21:10, pages 2382-2394.
Crossref
Sang-Yeon Cho, M.A. Brooke & N.M. Jokerst. (2003) Optical interconnections on electrical boards using embedded active optoelectronic components. IEEE Journal of Selected Topics in Quantum Electronics 9:2, pages 465-476.
Crossref
N.M. Jokerst, M.A. Brooke, Sang-Yeon Cho, S. Wilkinson, M. Vrazel, S. Fike, J. Tabler, Yoong Joon Joo, Sang-Woo Seo, D.S. Wills & A. Brown. (2003) The heterogeneous integration of optical interconnections into integrated microsystems. IEEE Journal of Selected Topics in Quantum Electronics 9:2, pages 350-360.
Crossref
Sang-Yeon Cho, J.D. Hall, A. Chellappa, N.M. Jokerst & M. Brooke. (2003) High speed optical interconnection using embedded PDs on electrical boards. High speed optical interconnection using embedded PDs on electrical boards.
P.S. Ho, J. Liu, M. Morgen, M. Kiene, J.-H. Zhao & C. Hu. 2003. Interlayer Dielectrics for Semiconductor Technologies. Interlayer Dielectrics for Semiconductor Technologies 37 76 .
Sang-Yeon Cho, Sang-Woo Seo, M.A. Brooke & N.M. Jokerst. (2002) Integrated detectors for embedded optical interconnections on electrical boards, modules, and integrated circuits. IEEE Journal of Selected Topics in Quantum Electronics 8:6, pages 1427-1434.
Crossref
J.M. Snodgrass, D. Pantelidis, M.L. Jenkins, J.C. Bravman & R.H. Dauskardt. (2002) Subcritical debonding of polymer/silica interfaces under monotonic and cyclic loading. Acta Materialia 50:9, pages 2395-2411.
Crossref
J. A. Moore & Chi-I. Lanc. 2002. Fluoropolymers 1: Synthesis. Fluoropolymers 1: Synthesis 273 312 .
Takahito Itoh. (2001) Polymerizations and polymers of quinonoid monomers. Progress in Polymer Science 26:7, pages 1019-1059.
Crossref
Robert J. Hohlfelder, Daniel A. Maidenberg, Reinhold H. Dauskardt, Yueguang Wei & W. Hutchinson. (2011) Adhesion of benzocyclobutene-passivated silicon in epoxy layered structures. Journal of Materials Research 16:1, pages 243-255.
Crossref
John M. Warakomski, William C. Pike & Robert A. Devries. (2000) Benzocyclobutenes as styrene monomer scavengers and molecular weight ?stabilizers? in atactic and syndiotactic polystyrenes. Journal of Applied Polymer Science 78:11, pages 2008-2015.
Crossref
S Poulin, D.Q Yang, E Sacher, C Hyett & T.H Ellis. (2000) The surface structure of Dow Cyclotene 3022, as determined by photoacoustic FTIR, confocal Raman and photoelectron spectroscopies. Applied Surface Science 165:1, pages 15-22.
Crossref
Michael MorgenE. Todd RyanJie-Hua ZhaoChuan HuTaiheui ChoPaul S. Ho. (2000) Low Dielectric Constant Materials for ULSI Interconnects. Annual Review of Materials Science 30:1, pages 645-680.
Crossref
Hans‐Georg Elias. 2000. Ullmann's Encyclopedia of Industrial Chemistry. Ullmann's Encyclopedia of Industrial Chemistry.
Robert Talevi, Heidi Gundlach, Zailong Bian, Andreas Knorr, Maarten van Gestel, Sumant Padiyar, Alain E. Kaloyeros, Robert E. Geer, Edward O. Shaffer & Steve Martin. (2000) Material and process studies in the integration of plasma-promoted chemical-vapor deposition of aluminum with benzocyclobutene low-dielectric constant polymer. Journal of Vacuum Science & Technology B: Microelectronics and Nanometer Structures Processing, Measurement, and Phenomena 18:1, pages 252-261.
Crossref
José L. Segura & Nazario Martín. (1999) o -Quinodimethanes:  Efficient Intermediates in Organic Synthesis . Chemical Reviews 99:11, pages 3199-3246.
Crossref
Michael Morgen, Jie-Hua Zhao, Chuan Hu, Taiheui Cho, Paul S. Ho & E. Todd. (1999) Low dielectric constant materials for advanced interconnects. JOM 51:9, pages 37-40.
Crossref
Keisuke Chino, Toshikazu Takata & Takeshi Endo. (1999) Polymerization ofo-quinodimethanes. III. Polymerization ofo-quinodimethanes bearing electron-withdrawing groups formedin situby thermal ring-opening isomerization of corresponding benzocyclobutenes. Journal of Polymer Science Part A: Polymer Chemistry 37:10, pages 1555-1563.
Crossref
Elizabeth Pingel, Larry J. Markoski, Gary E. Spilman, Brendan J. Foran, Tao Jiang & David C. Martin. (1999) Thermally crosslinkable thermoplastic PET-co-XTA copolyesters. Polymer 40:1, pages 53-64.
Crossref
Michael A. Meador. (1998) RECENT ADVANCES IN THE DEVELOPMENT OF PROCESSABLE HIGH-TEMPERATURE POLYMERS. Annual Review of Materials Science 28:1, pages 599-630.
Crossref
Amnon Stanger, Alona Shachter & Roland Boese. (1998) Stereocontrol in nickel mediated syntheses of cyclobutabenzenes. The selective preparation of cis and trans derivatives of 7,8-dibromocyclobutabenzene. Tetrahedron 54:7, pages 1207-1220.
Crossref
Patrick T. Mather, Kevin P. Chaffee, Angel Romo-Uribe, Gary E. Spilman, Tao Jiang & David C. Martin. (1997) Thermally crosslinkable thermotropic copolyesters: synthesis, characterization, and processing. Polymer 38:24, pages 6009-6022.
Crossref
C.T. Wright & D.R. Paul. (1997) Feasibility of thermal crosslinking of polyarylate gas-separation membranes using benzocyclobutene-based monomers. Journal of Membrane Science 129:1, pages 47-53.
Crossref
Loon-seng Tan & N. Venkatasubramanian. (1996) Aromatic polyamides containing keto-benzocyclobutene pendants. Journal of Polymer Science Part A: Polymer Chemistry 34:17, pages 3539-3549.
Crossref
Keisuke Chino, Toshikazu Takata & Takeshi Endo. (2003) Polymerization of o ‐quinodimethanes, 1. Radical polymerization of 1‐methoxy‐ o ‐quinodimethane formed in situ by thermal isomerization of 1‐methoxy‐benzocyclobutene . Macromolecular Rapid Communications 17:5, pages 339-345.
Crossref
Ying‐Hung So, Ashish Sen, Peter Kim & Var St. Jeor. (2003) Molecular composite fibers from rigid rod polymers and thermoset resin matrixes. Journal of Polymer Science Part A: Polymer Chemistry 33:17, pages 2893-2899.
Crossref
Chunping Gao & Allan S. Hay. (2003) Poly(Ether sulfone)s made from 4,4′‐dihydroxystilbene and 4,4′‐difluorodiphenylsulfone: Synthesis, crosslinking, and epoxidation with hydrogen peroxide. Journal of Polymer Science Part A: Polymer Chemistry 33:16, pages 2731-2739.
Crossref
C.F. Kane & R.R. Krchnavek. (1995) Processing and characterization of benzocyclobutene optical waveguides. IEEE Transactions on Components, Packaging, and Manufacturing Technology: Part B 18:3, pages 565-571.
Crossref
C.F. Kane & R.R. Krchnavek. (1995) Benzocyclobutene optical waveguides. IEEE Photonics Technology Letters 7:5, pages 535-537.
Crossref
G. E. Spilman, T. Jiang, Q. Lu & D. C. Martin. (2011) Synthesis And Properties Of Crosslinkable Phenylacetylene Donor-Acceptor Molecules. MRS Proceedings 413.
Crossref
Robert A. DeVries, Reed A. Shick & Bethany K. Johnson. (2011) Digital Optical Imaging Of Benzocyclobutene (Bcb) Thin Films On Silicon Wafers. MRS Proceedings 381.
Crossref
Kenneth A. Walker, Larry J. Markoski, Gary A. Deeter, Gary E. Spilman, David C. Martin & Jeffrey S. Moore. (1994) Crosslinking chemistry for high-performance polymer networks. Polymer 35:23, pages 5012-5017.
Crossref
S. Bothra, M. Kellam & P. Garrou. (1994) Feasibility of BCB as an interlevel dielectric in integrated circuits. Journal of Electronic Materials 23:8, pages 819-825.
Crossref
Jennifer Rigney, Monica D. Little & David C. Martin. (2003) Swelling studies of crosslinked poly( p ‐phenylene terephthalamide) copolymers in sulfuric acid . Journal of Polymer Science Part B: Polymer Physics 32:6, pages 1017-1021.
Crossref
R. A. Kirchhoff & K. J. Bruza. 1994. High Performance Polymers. High Performance Polymers 1 66 .
R.A. Kirchhoff & K.J. Bruza. (1993) Benzocyclobutenes in polymer synthesis. Progress in Polymer Science 18:1, pages 85-185.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.