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Year 2018, Volume: 46 Issue: 1, 61 - 68, 01.03.2018

Abstract

References

  • K.E. Uhrich, S.M. Cannizzaro, R.S. Langer, K.M. Shakesheff, Polymeric systems for controlled drug release, Chem. Rev., 99 (1999) 3181-3198.
  • G. Chen, T. Ushida, T. Tateishi, Scaffold design for tissue engineering Macromol. Biosci., 2 (2002) 67-77.
  • C.M. Agrawal, K.F. Haas, D.A. Leopold, H.G. Clark, Evaluation of poly(L-lactic acid) as a material for intravascular polymeric stents, Biomaterials, 13 (1992) 176-182.
  • A. Lendlein, R. Langer, Biodegradable, elastic shape-memory polymers for potential biomedical applications, Science, 296 (2002) 1673-1676.
  • F.B. Bujans, R. Martinez, M.Y.Y. Pedram, P. Ortiz, H. Frey, Water-soluble polyesters from long chain alkylesters of citric acid and poly(ethylene glycol), Eur. Polym. J., 43 (2007) 1288-1301.
  • J.F. Lutz, Sequence-controlled polymerizations: the next Holy Grail in polymer science, Polym. Chem., 1 (2010) 55-62.
  • Y. Tachibana, T. Masuda, M. Funabashi, M. Kunioka, Chemical synthesis of fully biomass-based poly(butylene succinate) from inedible-biomassbased furfural and evaluation of its biomass carbon ratio, Biomacromolecules, 11 (2010) 2760-2765.
  • B.G. Amsden, G. Misra, F. Gu, H.M. Younes, Synthesis and characterization of a photo-cross-linked biodegradable elastomer, Biomacromolecules, 5 (2004) 2479-2486.
  • Y. Wang, G.A. Ameer, B.J. Sheppard, R.A. Langer, Tough biodegradable elastomer, Nat. Biotechnol., 20 (2002) 602-606.
  • A.H. Brown, V.V. Sheares, Amorphous unsaturated aliphatic polyesters derived from dicarboxylic monomers synthesized by Diels−Alder chemistry, Macromolecules, 40 (2007) 4848-4853.
  • R. Baumgartner, Z. Song, Y. Zhang, J. Cheng, Functional polyesters derived from alternating copolymerization of norbornene anhydride and epoxides, Polymer Chemistry, 6 (2015) 3586-3590.
  • A.B. Cherian, B.T. Abraham, E.T. Thachil, Modification of unsaturated polyester resin by polyurethane prepolymers, J. App. Polym. Sci., 100 (2006) 449- 456.
  • C. Ai, G. Gong, X. Zhao, P. Liu, Determination of carboxyl content in carboxylated nitrile butadiene rubber (XNBR) after degradation via olefin cross metathesis, Polym. Test., 60 (2017) 250-252.
  • L. Fournier, C. Robert, S. Pourchet, A. Gonzales, L. Williams, J. Prunet, C.M. Thomas, Facile and efficient chemical functionalization of aliphatic polyesters by cross metathesis, Polym. Chem., 7 (2016) 3700-3704.
  • F. Sinclair, L. Chen, B.W. Greenland, M.P. Shaver, Installing multiple functional groups on biodegradable polyesters via post-polymerization olefin crossmetathesis, Macromolecules, 49 (2016) 6826-6834.
  • X. Michel, S. Fouquay, G. Michaud, F. Simon, J.M. Brusson, J.F. Carpentier, S.M. Guillaume, α,ωBis(trialkoxysilyl) difunctionalized polycyclooctenes from ruthenium-catalyzed chain-transfer ring-opening metathesis polymerization, Polym. Chem., 7 (2016) 4810-4823.
  • Y. Tachibana, M. Yamahata, K. Kasuya, Synthesis and characterization of a renewable polyester containing oxabicyclic dicarboxylate derived from furfural, Green Chem., 15 (2013) 1318-1325.
  • R.F. Fischer, Polyesters from epoxides and anhydrides, J. Polym. Sci. Part A: Polym. Chem., 44 (1960) 155-172.

Modification of Functional Polyesters Bearing Norbornene Moieties via Olefin Metathesis Reactions

Year 2018, Volume: 46 Issue: 1, 61 - 68, 01.03.2018

Abstract

I
n this study, unsaturated functional polyester derivatives were synthesized via polycondensation reactions
of 5-norbornene-2,3-dicarboxylic anhydride and 1,6-hexanediol. Functional unsaturated polyesters were modified
using methyl acrylate as ring opening/cross-metathesis reaction partner. The solubility and hydrophobic/hydrophilic
character of polyester was tuned by integrating allyl end capped poly(ethyleneglycol) by
ring opening/cross-metathesis reactions. Norbornene moiety of unsaturated polyesters allowed us to use ring
opening metathesis polymerization reactions to form side-chain poly(norbornene) on main polyester chain
using Grubbs 1st, 3rd and Hoveyda-Grubbs 2nd generation catalysts as initiators, resulting in gel-like materials. 

References

  • K.E. Uhrich, S.M. Cannizzaro, R.S. Langer, K.M. Shakesheff, Polymeric systems for controlled drug release, Chem. Rev., 99 (1999) 3181-3198.
  • G. Chen, T. Ushida, T. Tateishi, Scaffold design for tissue engineering Macromol. Biosci., 2 (2002) 67-77.
  • C.M. Agrawal, K.F. Haas, D.A. Leopold, H.G. Clark, Evaluation of poly(L-lactic acid) as a material for intravascular polymeric stents, Biomaterials, 13 (1992) 176-182.
  • A. Lendlein, R. Langer, Biodegradable, elastic shape-memory polymers for potential biomedical applications, Science, 296 (2002) 1673-1676.
  • F.B. Bujans, R. Martinez, M.Y.Y. Pedram, P. Ortiz, H. Frey, Water-soluble polyesters from long chain alkylesters of citric acid and poly(ethylene glycol), Eur. Polym. J., 43 (2007) 1288-1301.
  • J.F. Lutz, Sequence-controlled polymerizations: the next Holy Grail in polymer science, Polym. Chem., 1 (2010) 55-62.
  • Y. Tachibana, T. Masuda, M. Funabashi, M. Kunioka, Chemical synthesis of fully biomass-based poly(butylene succinate) from inedible-biomassbased furfural and evaluation of its biomass carbon ratio, Biomacromolecules, 11 (2010) 2760-2765.
  • B.G. Amsden, G. Misra, F. Gu, H.M. Younes, Synthesis and characterization of a photo-cross-linked biodegradable elastomer, Biomacromolecules, 5 (2004) 2479-2486.
  • Y. Wang, G.A. Ameer, B.J. Sheppard, R.A. Langer, Tough biodegradable elastomer, Nat. Biotechnol., 20 (2002) 602-606.
  • A.H. Brown, V.V. Sheares, Amorphous unsaturated aliphatic polyesters derived from dicarboxylic monomers synthesized by Diels−Alder chemistry, Macromolecules, 40 (2007) 4848-4853.
  • R. Baumgartner, Z. Song, Y. Zhang, J. Cheng, Functional polyesters derived from alternating copolymerization of norbornene anhydride and epoxides, Polymer Chemistry, 6 (2015) 3586-3590.
  • A.B. Cherian, B.T. Abraham, E.T. Thachil, Modification of unsaturated polyester resin by polyurethane prepolymers, J. App. Polym. Sci., 100 (2006) 449- 456.
  • C. Ai, G. Gong, X. Zhao, P. Liu, Determination of carboxyl content in carboxylated nitrile butadiene rubber (XNBR) after degradation via olefin cross metathesis, Polym. Test., 60 (2017) 250-252.
  • L. Fournier, C. Robert, S. Pourchet, A. Gonzales, L. Williams, J. Prunet, C.M. Thomas, Facile and efficient chemical functionalization of aliphatic polyesters by cross metathesis, Polym. Chem., 7 (2016) 3700-3704.
  • F. Sinclair, L. Chen, B.W. Greenland, M.P. Shaver, Installing multiple functional groups on biodegradable polyesters via post-polymerization olefin crossmetathesis, Macromolecules, 49 (2016) 6826-6834.
  • X. Michel, S. Fouquay, G. Michaud, F. Simon, J.M. Brusson, J.F. Carpentier, S.M. Guillaume, α,ωBis(trialkoxysilyl) difunctionalized polycyclooctenes from ruthenium-catalyzed chain-transfer ring-opening metathesis polymerization, Polym. Chem., 7 (2016) 4810-4823.
  • Y. Tachibana, M. Yamahata, K. Kasuya, Synthesis and characterization of a renewable polyester containing oxabicyclic dicarboxylate derived from furfural, Green Chem., 15 (2013) 1318-1325.
  • R.F. Fischer, Polyesters from epoxides and anhydrides, J. Polym. Sci. Part A: Polym. Chem., 44 (1960) 155-172.
There are 18 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Bengi Özgün Öztürk

Publication Date March 1, 2018
Acceptance Date October 18, 2017
Published in Issue Year 2018 Volume: 46 Issue: 1

Cite

APA Öztürk, B. Ö. (2018). Modification of Functional Polyesters Bearing Norbornene Moieties via Olefin Metathesis Reactions. Hacettepe Journal of Biology and Chemistry, 46(1), 61-68.
AMA Öztürk BÖ. Modification of Functional Polyesters Bearing Norbornene Moieties via Olefin Metathesis Reactions. HJBC. March 2018;46(1):61-68.
Chicago Öztürk, Bengi Özgün. “Modification of Functional Polyesters Bearing Norbornene Moieties via Olefin Metathesis Reactions”. Hacettepe Journal of Biology and Chemistry 46, no. 1 (March 2018): 61-68.
EndNote Öztürk BÖ (March 1, 2018) Modification of Functional Polyesters Bearing Norbornene Moieties via Olefin Metathesis Reactions. Hacettepe Journal of Biology and Chemistry 46 1 61–68.
IEEE B. Ö. Öztürk, “Modification of Functional Polyesters Bearing Norbornene Moieties via Olefin Metathesis Reactions”, HJBC, vol. 46, no. 1, pp. 61–68, 2018.
ISNAD Öztürk, Bengi Özgün. “Modification of Functional Polyesters Bearing Norbornene Moieties via Olefin Metathesis Reactions”. Hacettepe Journal of Biology and Chemistry 46/1 (March 2018), 61-68.
JAMA Öztürk BÖ. Modification of Functional Polyesters Bearing Norbornene Moieties via Olefin Metathesis Reactions. HJBC. 2018;46:61–68.
MLA Öztürk, Bengi Özgün. “Modification of Functional Polyesters Bearing Norbornene Moieties via Olefin Metathesis Reactions”. Hacettepe Journal of Biology and Chemistry, vol. 46, no. 1, 2018, pp. 61-68.
Vancouver Öztürk BÖ. Modification of Functional Polyesters Bearing Norbornene Moieties via Olefin Metathesis Reactions. HJBC. 2018;46(1):61-8.

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