224
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of Copolymers Containing Double Spiro Orthocarbonate and Used as Anti-shrinkage Additives in Epoxy Resin Composite

, , , &

REFERENCES

  • Zhou , Y.Z. ; Ren , H. ; Lu , H.B. ; Meng , X.K. Preparation and characterization of a graphene oxide film modified by the covalent attachment of polysiloxane . Polym.-Plast. Technol. Eng. 2013 , 52 ( 6 ), 581 – 585 .
  • Zhang , J.H. ; Qiu , Q.H. ; Yek , W.Y. ; Wang , F.D. ; Jia , Z.X. ; Baochun Guo , B.C. ; Demin Jia , D.M. Preparation and application of a new curing agent for epoxy resin . Inter. J. Polym. Mater. Polym. Biomater. 2012 , 61 ( 7 ), 520 – 531 .
  • Patel , B.K. ; Patel , H.S. Synthesis, Characterization, and glass reinforcement of flame retardant acrylated poly(ester-amide) and flame retardant poly(ester-imide) resins based on brominated epoxy resin . Inter. J. Polym. Mater. Polym. Biomater. 2012 , 62 ( 8 ), 455 – 461 .
  • He , P.S. ; Zhou , Z.Q. ; Pan , C.Y. An epoxy resin copolymer with zero shrinkage . J. Mater. Sci. 1989 , 24 ( 5 ), 1528 – 1532 .
  • Chappelow , C.C. ; Pinzino , C.S. ; Chen , S.S. ; Kotha , S.P. ; Eick , J.D. ; Alan , G.G. Tetraoxaspiroalkanes for polymerization stress reduction of silorane resins . J. Appl. Polym. Sci. 2008 , 108 ( 6 ), 3738 – 47 .
  • Ge , J. ; Trujillo-Lemon , M. ; Stansbury , J.W. 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 2006 , 39 ( 26 ), 8968 – 8976 .
  • Wang , C.S. ; Zhou , B.L. Study on epoxy resin modified with prepolymers containing spiro orthocarnonate . J. Mater. Sci. Lett. 1999 , 18 , 1259 – 1262 .
  • Chen , W.S. ; Chang , Y.L. ; Hsiang , H.I. ; Hsu , F.C. ; Shen , Y.H. ; Yen , F.S. Mechanical and dielectric properties of NiZn ferrite powders-CTBN modified epoxy resin coatings . Polym.-Plast. Technol. Eng. 2011 , 50 ( 6 ), 568 – 572 .
  • Fotsing , E.R. ; Miron , F. ; Eury , Y. ; Ross , A. ; Ruiz , E. Bonding analysis of carbon/epoxy composites with viscoelastic acrylic adhesive . Compos. Pt. B: Eng. 2012 , 43 ( 5 ), 2087 – 2093 .
  • Liu , Y. ; Wu , W. ; Chen , Y. ; Shi , P.P. ; Liu , M.C. ; Wu , X. The effects of polyamic acid on curing behavior, thermal stability, and mechanical properties of epoxy/DDS system . J. Appl. Polym. Sci. 2013 , 127 ( 4 ), 3213 – 3220 .
  • Thompson , V.P. ; Williams , E.F. ; Bailey , W.J. Dental resins with reduced shrinkage during hardening . J. Dent Res. 1979 , 58 ( 5 ), 1522 – 1532 .
  • Bailey , W.J. ; Sun , R.L. Polymerization of a spiro ortho ester . Amer. Chem. Soc. Div. Polym. Chem. Prepr. 1972 , 13 ( 1 ), 281 – 286 .
  • Bailey , W.J. , Iwama , H. ; Tsushima , R. Synthesis of elastomers by cationic polymerization with expansion in volume . J. Polym. Sci. 1976 , 56 ( 1 ), 117 – 127 .
  • Sakai , S. The synthesis of sulfur-containing spiroorthocarbonates . J. Org. Chem. 1970 , 35 ( 7 ), 2347 – 2351 .
  • Ortiz , R.A. ; Duarte , M.L.B. ; Gomez , A.G.S. ; Sangermano , M. ; Valdez , A.E.G. Novel diol spiroorthocarbonates derived from glycerol as anti-shrinkage additives for the cationic photopolymerization of epoxy monomers . Polym. Int. 2010 , 59 ( 5 ), 680 – 685 .
  • Chappelow , C.C. ; Pinzino , C.S. ; Chen , S.S. Photopolymerization of a novel tetraoxaspiroundecane and silicon-containing oxiranes . J. Appl. Polym. Sci. 2007 , 103 ( 1 ), 336 – 344 .
  • Sangermano , M. ; Giannelli , S. ; Ortiz , R.A. ; Duarte , M.L.B. ; Gonzalez , A.K.R. ; Valdez , A.E.G. Synthesis of an oxetane-functionalized hemispiroorthocarbonate used as a low-shrinkage additive in the cationic ultraviolet curing of oxetane monomers . J. Appl. Polym. Sci. 2009 , 112 ( 3 ), 1780 – 1787 .
  • Chappelow , C.C. ; Pinzino , C.S. ; Chen , S.S. ; Kotha , S.P. ; Glaros , A.G. ; Eick , J.D. Tetraoxaspiroalkanes for polymerization stress reduction of silorane resins . J. Appl. Polym. Sci. 2008 , 108 ( 6 ), 3738 – 3747 .
  • Sun , H.Y. ; Chang , K.K. Synthesis of a novel spiroorthocarbonate containing bisphenol-a unit and its application to the dental composites . Macromol. Res. 2010 , 18 ( 10 ), 1013 – 1020 .
  • Sun , X. ; Li , Y.C. ; Xiong , J. ; Hu , X.Y. ; Chen , J.H. Shrinkage properties of a modified dental resin composites containing a novel spiro-orthocarbonate expanding monomer . Mater. Lett. 2011 , 65 , 3586 – 3589 .
  • Wang , D.Y. ; Cai , X.X. ; Qu , M.H. ; Liu , Y. Preparation and flammability of a novel intumescent flame-retardant poly(ethylene-co-vinyl acetate) system . Polym. Degrad. Stab. 2008 , 93 ( 12 ), 2186 – 2192 .
  • Vijayakumar , C.T. ; Mathan , N.D. ; Sarasvathy , V. ; Rajkumar , T. ; Thamaraichelvan , A. Synthesis and thermal properties of spiro phosphorus compounds . J. Therm. Anal. Calorim. 2010 , 101 ( 1 ), 281 – 287 .
  • Chen , D.Q. ; Wang , Y.Z. ; Hu , X.P. Flame-retardant and anti-dripping effects of a novel char-forming flame retardant for the treatment of poly(ethylene terephthalate) fabrics . Polym. Degrad. Stabil. 2005 , 88 ( 2 ), 349 – 356 .
  • Li , L.K. ; Wei , P. ; Jun , L.J. Synthesis and characterization of a novel flame retardant and its application in polycarbonate . J. Fire Sci. 2010 , 28 ( 6 ), 523 – 538 .
  • Liu , Y. ; Wang , D.Y. ; Wang , J.S. ; Song , P. , Wang , Y.Z. A novel intumescent flame-retardant LDPE system and its thermo-oxidative degradation and flame-retardant mechanisms . Polym. Advan. Technol. 2008 , 19 ( 11 ), 1566 – 1575 .
  • Sharma , P. ; Kumar , A. ; Sahu , V. Synthesis of bioactive spiro-2-[30-(20-phenyl)-3 hindolyl]-1-aryl-3-phenylaziridines and SAR studies on their antimicrobial behavior . Med. Chem. Res. 2009 , 18 ( 5 ), 383 – 395 .
  • Acosta Ortiz , R. ; Berlanga Duarte , M.L. ; Robles Olivares , J.L. Synthesis of the fluorene spiroorthocarbonate and the evaluation of its antishrinking activity in the cationic photopolymerization of an epoxy resin . Design. Monom. Polym. 2013 , 16 ( 4 ), 323 – 329 .
  • Ahadi , S. ; Abaszadeh , M. ; Bazgir , A. Organocatalytic three-component cascade reaction for the synthesis of spiro[indeno[1,2-b]furan]-triones . Mol. Divers 2012 , 16 ( 2 ), 299 – 306 .
  • Kouznetsov , V.V. Quinolines spiro annulated at heterocyclic fragment; Synthesis and properties. J. Heterocyclic Chem. 2005, 42 (1), 39–59.
  • Kato , S. ; Yoshino , T. ; Shibasaki , M. ; Kanai , M. ; Matsunaga , S. Catalytic asymmetric synthesis of spirooxindoles by a mannich-type reaction of isothiocyanato oxindoles . Angew Chem. Int. Ed. 2012 , 51 ( 28 ), 7007 – 7010 .
  • Czaderski , C. ; Martinelli , E. ; Michels , J. ; Motavalli , M. Effect of curing conditions on strength development in an epoxy resin for structural strengthening . Compos. Pt. B: Eng. 2012 , 43 ( 2 ), 398 – 410 .
  • Chappelow , C.C. ; Pinzino , C.S. ; Chen , S.S. ; Jeang , L. ; Eick , J.D. Photopolymerization of a novel tetraoxaspiroundecane and silicon-containing oxiranes . J. Appl. Polym. Sci. 2007 , 103 ( 1 ), 336 – 344 .
  • Kume , M. ; Maki , Y. ; Ochiai , B. ; Endo , T. Synthesis of copolymers containing a spiro orthocarbonate moiety and evaluation of the volume change during their cationic crosslinking . J. Polym. Sci. Pt. A: Polym. Chem. 2006 , 44 ( 24 ), 7040 – 7053 .
  • Zeng , Y. ; Liu , H.Y. ; Mai , Y.W. ; Du , X.D. Improving interlaminar fracture toughness of carbon fibre/epoxy laminates by incorporation of nano-particles . Compos. Pt. B: Eng. 2012 , 43 ( 1 ), 90 – 94 .
  • Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lpte.

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.