665
Views
9
CrossRef citations to date
0
Altmetric
Articles

Synthesis of the fluorene spiroorthocarbonate and the evaluation of its antishrinking activity in the cationic photopolymerization of an epoxy resin

, , &
Pages 323-329 | Received 02 May 2012, Published online: 03 Dec 2012

References

  • May , IA . 1988 . Epoxy resins , New York , NY : Marcel Dekker .
  • Takata , T and Endo , T . 1993 . Recent advances in the development of expanding monomers: synthesis, polymerization and volume change . Prog. Polym. Sci. , 18 : 839 – 870 .
  • Penco , M , Donetti , R , Mendichi , R and Ferruti , P . 1998 . New poly(ester-carbonate) multi-block copolymers based on poly(lactic-glycolic acid) and poly(ϵ-caprolactone) segments . Macromol. Chem. Phys. , 199 : 1737 – 1745 .
  • Bailey , WJ , Iwama , H and Tsushima , R . 1976 . Synthesis of elastomers by cationic polymerization with expansion in volume . J. Polym. Sci. , 56 : 117 – 127 .
  • Bailey , WJ and Endo , T . 1978 . Radical ring-opening polymerization and copolymerization with expansion in volume . J. Polym. Sci. , 64 : 17 – 26 .
  • Bailey WJ, Polycyclic ring-opened polymers. United States patent US 4,387,215. 1983.
  • Ge , J , Trujillo-Lemon , M and Stansbury , JW . 2006 . A mechanistic and kinetic study of the photoinitiated cationic double ring-opening polymerization of 2-methylene-7-phenyl-1,4,6,9-tetraoxa-spiro[4.4]nonane . Macromolecules. , 39 : 8968 – 8976 .
  • Nagai , D , Nishida , M , Nagasawa , T , Ochiai , B , Miyazaki , K and Endo , T . 2006 . Non-shrinking networked materials from the cross-linking copolymerization of spiroorthocarbonate with bifunctional oxetane . Macromol. Rapid Commun. , 27 : 921 – 925 .
  • Sonmez , HB and Wudl , F . 2003 . Synthesis of polymers based on spiroorthocarbonates . Polym. Preprints. , 44 : 803
  • Guo YM, Zou YF, Pan CY. Investigation on cationic ring-opening polymerization of 1,5,7,11-tetraoxaspiro [5,5] undecane in the presence of low molecular weight tetraols. Polymer. 2001;42:1337–1344.
  • Eick , JD , Smith , RE , Pinzino , CS , Kotha , SP , Kostoritz , EL and Chapelow , CC . 2005 . Photopolymerization of developmental monomers for dental cationically initiated matrix resins . Dent. Mater. , 21 : 384 – 390 .
  • Zhou , Z , Jin , B and He , P . 2002 . Copolymerization behavior and kinetics of an epoxy copolymer with zero shrinkage . J. Appl. Polym. Sci. , 84 : 1457 – 1464 .
  • Smith , RE , Pinzino , CS , Chappelow , CC , Holden , AJ , Kostoryz , EC , Guthrie , JR , Yourtee , DM and Eick , JD . 2004 . Photopolymerization of an expanding monomer with an aromatic dioxirane . J. Appl. Polym. Sci. , 92 : 62 – 71 .
  • Sangermano , M , Acosta Ortiz , R , Puente Urbina , BA , Berlanga Duarte , ML , Garcia Valdez , AE and Guerrero Santos , R . 2008 . Synthesis of an epoxy functionalized spiroorthocarbonate used as low shrinkage additive in cationic UV curing of an epoxy resin . Eur. Polym. J. , 44 : 1046 – 1052 .
  • Sangermano , M , Gianelli , S , Acosta Ortiz , R , Berlanga Duarte , ML , Rueda Gonzalez , AK and Garcia Valdez , AE . 2009 . Synthesis of an oxetane-functionalized hemispiroorthocarbonate used as a low-shrinkage additive in the cationic ultraviolet curing of oxetane monomers . J. Appl. Polym. Sci. , 112 : 1780 – 1787 .
  • Endo , T , Sato , H and Takata , T . 1987 . Synthesis and cationic polymerization of 3,9-dibenzyl-1,5,7,11-tetraoxaspiro[5.5]undecane . Macromolecules. , 20 : 1416 – 1419 .
  • Crivello , JV and Lee , JL . 1989 . Alkoxy-substituted diaryliodonium salt cationic photoinitiators . J. Polym. Sci., Part A: Polym. Chem. , 27 : 3951 – 3968 .
  • Acosta Ortiz R, Berlanga Duarte ML, Savage Gomez AG Sangermano M, Garcia Valdez AE Novel diol spiro orthocarbonates derived from glycerol as anti-shrinkage additives for the cationic photopolymerization of epoxy monomers Polym. Int. 2010;59:680–685.
  • Acosta Ortiz , R , Savage Gomez , AG , Berlanga Duarte , ML , Sangermano , M and Garcia Valdez , AE . 2012 . The effect of hydroxyspiro-orthocarbonates on the cationic photopolymerization of an epoxy resin and on the mechanical properties of the final polymer . Polym. Int. , 61 : 587 – 595 .
  • Park YJ, No KH, Kim JH, Suh IH. Synthesis and X-ray crystallographic characterization of spiro orthocarbonates. Bull. Korean Chem. Soc. 1992;13:375–381.

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:

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:

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.