Study of the Grafting of Bromoacetylated α-Hydroxy-ω-Methoxypoly(Ethyleneglycol) onto Anionically Activated Poly(∊-Caprolactone)
Abstract
Bromoacetylated α-hydroxy-ω methoxy-poly (ethyleneglycol) (M n = 2000 g mol −1 ) was allowed to react with a poly(∊ caprolactone) (M n = 53,700, M w /M n =(1.50) that was first activatedby removing some of the proton atoms borne by the carbon atoms locatedin -position of carbonyl groups using lithium N-N-diisopropylamide as basic reagent in tetrahydrofurane at 78°C under argon flow. The reaction resulted in the grafting of methoxy poly(ethylene glycol) segments to some of the poly("-caprolactone) chains. The resulting polymeric compounds were characterized by various analytical techniques including NMR, SEC, DSC, X-ray diffraction and contact angle. Various characteristics of the recovered compounds, namely degree of substitution, degree of crystallinity, glass transition and melting temperatures, hydrophilicity, were evaluated. It was concluded that grafting was effective but sometimes not all poly("-caprolactone) chains were modified, depending on experimental conditions. Moreover, 150 nm nanoparticles were obtained without any additional surfactant for a 0.74% substitution degree copolymer.
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Coupling of bromoacetylated α-hydroxymethoxypoly(ethylene-glycol) onto anionically activated PCL is a route to the PCL-g-PEO graft copolymer.
“The coupling of bromoacetylated α-hydroxymethoxypoly(ethyle-neglycol) onto anionically activated PCL is a route to the PCL-g-PEO graft copolymer [138].”
From Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization☆ (2008) · cites this paper as [138]
Cites
Hydrolytic degradation of devices based on poly(DL-lactic acid) size-dependence
Grizzi, I., Garreau, H., Li, S., & Vert, M. (1995) · Biomaterials · doi:10.1016/0142-9612(95)93258-f · Cited by 895 · see citing works
Self-citationStealth Me. PEG‐PLA Nanoparticles Avoid Uptake by the Mononuclear Phagocytes System
Bazile, D., Prud'homme, C., Bassoullet, M., Marlard, M., Spenlehauer, G., & Veillard, M. (1995) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.2600840420 · Cited by 635 · see citing works
Holland, S. J., Tighe, B. J., & Gould, P. L. (1986) · Journal of Controlled Release · doi:10.1016/0168-3659(86)90001-5 · Cited by 480 · see citing works
Oxidation of polyethylene glycols by alcohol dehydrogenase
Herold, D. A., Keil, K., & Bruns, D. E. (1989) · Biochemical Pharmacology · doi:10.1016/0006-2952(89)90151-2 · Cited by 403 · see citing works
Rashkov, I. B., Manolova, N. E., Li, S., Espartero, J. L., & Vert, M. (1996) · Macromolecules · doi:10.1021/ma950530t · Cited by 371 · see citing works
Self-citationDegradable polymers : principles and applications
SCOTT, G., & Gilead, D. (1995) · Cited by 316 · see citing works
Zhu, K. J., Xiangzhou, L., & Shilin, Y. (1990) · Journal of Applied Polymer Science · doi:10.1002/app.1990.070390101 · Cited by 313 · see citing works
Biodegradable Polymers and Plastics
(2004) · Chemistry International · doi:10.1515/ci.2004.26.2.30b · Cited by 293 · see citing works
Richter, A. W., & Akerblom, E. B. (2009) · International Archives of Allergy and Applied Immunology · doi:10.1159/000233309 · Cited by 282 · see citing works
Selective Enzymatic Degradations of Poly( l -lactide) and Poly(ε-caprolactone) Blend Films
Liu, L., Li, S., Garreau, H., & Vert, M. (2000) · Biomacromolecules · doi:10.1021/bm000046k · Cited by 272 · see citing works
Self-citationLABORATORY SYNTHESIS OF POLYETHYLENE GLYCOL DERIVATIVES
Harris, J. M. (1985) · Journal of macromolecular science. Part C, Reviews in macromolecular chemistry and physics/Journal of macromolecular science. Reviews in macromolecular chemistry and physics · doi:10.1080/07366578508081960 · Cited by 268 · see citing works
Pitt, C. G., Jeffcoat, A. R., Zweidinger, R. A., & Schindler, A. (1979) · Journal of Biomedical Materials Research · doi:10.1002/jbm.820130313 · Cited by 263 · see citing works
Li, S., Rashkov, I. B., Espartero, J. L., Manolova, N. E., & Vert, M. (1996) · Macromolecules · doi:10.1021/ma950531l · Cited by 262 · see citing works
Self-citationSynthesis and thermal properties of poly(ethylene glycol)-poly(ϵ-caprolactone) copolymers
Bogdanov, B. G., Vidts, A., Bulcke, A. V. D., Verbeeck, R. M. H., & Schacht, E. H. (1998) · Polymer · doi:10.1016/s0032-3861(97)00444-8 · Cited by 204 · see citing works
Li, Y., & Kissel, T. (1993) · Journal of Controlled Release · doi:10.1016/0168-3659(93)90155-x · Cited by 166 · see citing works
Polylactones, 22 ABA triblock copolymers of L ‐lactide and poly(ethylene glycol)
Kricheldorf, H. R., & Meier‐Haack, J. (1993) · Die Makromolekulare Chemie · doi:10.1002/macp.1993.021940229 · Cited by 160 · see citing works
Deng, X. M., Xiong, C., Cheng, L., & Xu, R. P. (1990) · Journal of Polymer Science Polymer Letters Edition · doi:10.1002/pol.1990.140281303 · Cited by 131 · see citing works
A Novel Route To Poly(ε-caprolactone)-Based Copolymers via Anionic Derivatization
Ponsart, S., Coudane, J., & Vert, M. (2000) · Biomacromolecules · doi:10.1021/bm005521t · Cited by 126 · see citing works
Self-citationShaffer, C. B., & Critchfield, F. H. (1947) · Journal of the American Pharmaceutical Association (Scientific ed ) · doi:10.1002/jps.3030360507 · Cited by 113 · see citing works
Cerrai, P., Tricoli, M., Andruzzi, F., Paci, M., & Paci, M. (1989) · Polymer · doi:10.1016/0032-3861(89)90126-2 · Cited by 111 · see citing works
Polymerization of lactones, 17. Synthesis of ethylene glycol‐ L ‐lactide block copolymers
Jedliński, Z., Kurcok, P., Wałach, W., Janeczek, H., & Radecka, I. (1993) · Die Makromolekulare Chemie · doi:10.1002/macp.1993.021940616 · Cited by 93 · see citing works
Biodegradation of aliphatic polyesters
Li, S., & Vert, M. (1995) · Springer eBooks · doi:10.1007/978-94-011-0571-2_4 · Cited by 88 · see citing works
Self-citationMorphological study of biodegradable PEO/PLA block copolymers
Younes, H., & Cohn, D. (1987) · Journal of Biomedical Materials Research · doi:10.1002/jbm.820211103 · Cited by 82 · see citing works
Synthesis and characterization of poly(oxyethylene)-poly(caprolactone) multiblock copolymers
Petrova, T., Manolova, N. E., Rashkov, I. B., Li, S., & Vert, M. (1998) · Polymer International · doi:10.1002/(sici)1097-0126(199804)45:4 · Cited by 69 · see citing works
Self-citationPoly(ester-ether-ester) block copolymers as biomaterials
Cerrai, P., Guerra, G., Lelli, L., Tricoli, M., Guerra, R. S. D., Cascone, M. G., & Giusti, P. (1994) · Journal of Materials Science Materials in Medicine · doi:10.1007/bf00121151 · Cited by 69 · see citing works
Synthèse et caractérisation de copolymères séquencés polyoxyéthylène/poly‐ε‐caprolactone
Perret, R., & Skoulios, A. (1972) · Die Makromolekulare Chemie · doi:10.1002/macp.1972.021560111 · Cited by 68 · see citing works
Li, S., Espartero, J. L., Foch, P., & Vert, M. (1997) · Journal of Biomaterials Science Polymer Edition · doi:10.1163/156856296x00237 · Cited by 65 · see citing works
Self-citationHydrolytic degradation of PCL/PEO copolymers in alkaline media
Li, S., Chen, X. H., Gross, R. A., & McCarthy, S. P. (2000) · Journal of Materials Science Materials in Medicine · doi:10.1023/a:1008920326988 · Cited by 63 · see citing works
Polycaprolactone–poly(ethylene glycol) block copolymer, I: synthesis and degradability in vitro
Shen‐Guo, W., & Qiu, B. (1993) · Polymers for Advanced Technologies · doi:10.1002/pat.1993.220040601 · Cited by 49 · see citing works
Jacquier-Gonod, V., Miola, C., Llauro, M., Monnet, C., & Hamaide, T. (1996) · Macromolecular Chemistry and Physics · doi:10.1002/macp.1996.021970411 · Cited by 24 · see citing works
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Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization☆
JEROME, C., & LECOMTE, P. (2008) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2008.02.008 · Cited by 590 · see citing works
Aliphatic Polyesters: Great Degradable Polymers That Cannot Do Everything
Vert, M. (2004) · Biomacromolecules · doi:10.1021/bm0494702 · Cited by 566 · see citing works
Self-citationRecent Developments in Ring-Opening Polymerization of Lactones
Lecomte, P., & Jérôme, C. (2011) · Advances in Polymer Science · doi:10.1007/12_2011_144 · Cited by 163 · see citing works
A review of polypeptide-based polymersomes
Zhao, L., Li, N., Wang, K., Shi, C., Zhang, L., & Luan, Y. (2014) · Biomaterials · doi:10.1016/j.biomaterials.2013.10.063 · Cited by 149 · see citing works
Novel Amphiphilic Poly(ε-caprolactone)-g-poly( l -lysine) Degradable Copolymers
Nottelet, B., Ghzaoui, A. E., Coudane, J., & Vert, M. (2007) · Biomacromolecules · doi:10.1021/bm700449c · Cited by 68 · see citing works
Self-citationA Chemoselective Approach to Grafting Biodegradable Polyesters
Taniguchi, I., Mayes, A. M., Chan, E. W. L., & Griffith, L. G. (2005) · Macromolecules · doi:10.1021/ma0487554 · Cited by 58 · see citing works
Huang, M., Coudane, J., Li, S., & Vert, M. (2005) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.20870 · Cited by 53 · see citing works
Self-citationCoudane, J., Nottelet, B., Mouton, J., Garric, X., & Berghe, H. V. D. (2022) · Molecules · doi:10.3390/molecules27217339 · Cited by 50 · see citing works
Self-citationCoumes, F., Darcos, V., Domurado, D., Li, S., & Coudane, J. (2013) · Polymer Chemistry · doi:10.1039/c3py00375b · Cited by 50 · see citing works
Self-citationPCL–PEG graft copolymers with tunable amphiphilicity as efficient drug delivery systems
Samad, A. A., Béthry, A., Koziolová, E., Netopilı́k, M., Etrych, T., Bakkour, Y., Coudane, J., Omar, F. E., & Nottelet, B. (2016) · Journal of Materials Chemistry B · doi:10.1039/c6tb01841f · Cited by 48 · see citing works
Self-citationTaniguchi, I., Kuhlman, W. A., Mayes, A. M., & Griffith, L. G. (2006) · Polymer International · doi:10.1002/pi.2139 · Cited by 47 · see citing works
Nottelet, B., Vert, M., & Coudane, J. (2008) · Macromolecular Rapid Communications · doi:10.1002/marc.200800037 · Cited by 41 · see citing works
Self-citationBuwalda, S. J., Samad, A. A., Jundi, A. E., Béthry, A., Bakkour, Y., Coudane, J., & Nottelet, B. (2017) · Journal of Colloid and Interface Science · doi:10.1016/j.jcis.2017.12.057 · Cited by 40 · see citing works
Self-citationSamad, A. A., Bakkour, Y., Coumes, F., Elomar, F., Coudane, J., & Nottelet, B. (2015) · Polymer Chemistry · doi:10.1039/c5py00391a · Cited by 38 · see citing works
Self-citationBolley, A., Mameri, S., & Dagorne, S. (2020) · Journal of Polymer Science · doi:10.1002/pol.20190214 · Cited by 8 · see citing works
Poddar, D., Singh, A., Bansal, S., Thakur, S., & Jain, P. (2022) · Journal of the Indian Chemical Society · doi:10.1016/j.jics.2022.100537 · Cited by 5 · see citing works
Synthesis and Fabrication of Polyesters as Biomaterials
Lecomte, P., & Jérôme, C. (2013) · CRC Press eBooks · doi:10.1201/b13757-2 · Cited by 3 · see citing works
Polyesters as Biomaterials: Synthesis and Fabrication
Lecomte, P., & Jérôme, C. (2016) · Taylor & Francis eBooks · doi:10.1081/e-ebpp-120052251 · Cited by 1 · see citing works
Metal Enolates in Polymer Science and Technology
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Lecomte, P., & Jérôme, C. (2017) · Patai's chemistry of functional groups · doi:10.1002/9780470682531.pat0904
- Authors
- Ponsart, S., Coudane, J., McGrath, J., & Vert, M.
- Affiliations
- Centre National de la Recherche Scientifique (FR)
- Corresponding author
- Coudane, Jean
- Venue
- Journal of Bioactive and Compatible Polymers
- Publisher
- SAGE Publications
- Published
- 2002-11
- Volume
- 17
- Issue
- 6
- Pages
- 417-432
- ISSN
- 0883-9115 (ISSN-L)
- 1530-8030
- OpenAlex
- W2107238040
- Cited by
- 24
- References
- 30
- Citations by year
- 2022: 2 · 2020: 1 · 2019: 2 · 2017: 2 · 2016: 2 · 2015: 1 · 2013: 3
- FWCI
- 0.64
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Bioactive and Compatible Polymers (publishedVersion)
- Funders
- National Science Foundation
- Fondation de France
- Topics
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Materials Science › Surfaces, Coatings and Films › Polymer Surface Interaction Studies
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Keywords
- graft copolymerization, polycaprolactone, degree of substitution, crystallinity, glass transition, melting point, hydrophilicity, nanoparticle formation, biodegradable polymers
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