green technology; radical polymerization; atom transfer radical polymerization (ATRP); (meth)acrylate
Abstract :
[en] Macromolecular fluorinated ligands were prepared according to a three-step strategy that consists of the random copolymerization of heptadecafluorodecyl acrylate and 2-hydroxyethylacrylate, followed by the esterification of the pendant hydroxyl groups with acryloyl chloride and the Michael-type addition of tetraethyldiethylenetriamine onto the acrylic double bonds of the polymeric chains. These fluorinated macroligands were successfully used in the atom transfer radical polymerization of MMA catalyzed by a copper salt in a fluorinated solvent. The polymerization control was analyzed in relation to the copper salt, the initiator and the molecular weight and composition of the macroligand before being extended to the heterogeneous ATRP of MMA in scCO2.
Research Center/Unit :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Grignard, Bruno ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Jérôme, Christine ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Calberg, Cédric ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Jérôme, Robert ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Detrembleur, Christophe ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
Atom transfer radical polymerization of MMA with a macromolecular ligand in a fluorinated solvent and in supercritical carbon dioxide
BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique F.R.S.-FNRS - Fonds de la Recherche Scientifique FRIA - Fonds pour la Formation à la Recherche dans l'Industrie et dans l'Agriculture
Commentary :
The authors acknowledge European Polymer Journal (Elsevier) for allowing them to archive this paper.
scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.
Bibliography
Matyjaszewski K., and Xia J. Atom transfer radical polymerization. Chem Rev 101 9 (2001) 2921-2990
Fischer H. The persistent radical effect in controlled radical polymerizations. J Polym Sci Part A: Polym Chem 37 13 (1999) 1885-1901
Matyjaszewski K. Radical nature of Cu-catalyzed controlled radical polymerizations (atom transfer radical polymerization). Macromolecules 31 15 (1998) 4710-4717
Xia J., Zhang X., and Matyjaszewski K. Effect of ligands on copper-mediated atom transfer radical polymerization. Polym Mater Sci Eng 80 (1999) 453-454
Xia J., and Matyjaszewski K. Controlled/"living" radical polymerization. Atom transfer radical polymerization using multidentate amine ligands. Macromolecules 30 25 (1997) 7697-7700
Xia J., Gaynor S.G., and Matyjaszewski K. Controlled/"living" radical polymerization. Atom transfer radical polymerization of acrylates at ambient temperature. Macromolecules 31 17 (1998) 5958-5959
Xia J., and Matyjaszewski K. Controlled/"living" radical polymerization. Atom transfer radical polymerization catalyzed by copper(I) and picolylamine complexes. Macromolecules 32 8 (1999) 2434-2437
Shen Youqing. Atom transfer radical polymerization and its continuous process. PhD thesis, McMaster University, Canada; 2001.
Hjeresen D.L., Schutt D.L., and Boese J.M. Green chemistry and education. J Chem Educ 77 12 (2000) 1543-1544
Cann M.C., and Connely M. Real-world cases in green chemistry (2000), ACS, Washington, DC
In: Ryan M., and Tinnesand M. (Eds). Introduction to green chemistry (2002), ACS, Washington, DC
Woods H.M., Silva M.M.C.G., Nouvel C., Shakesheff K.M., and Howdle S.M. Materials processing in supercritical carbon dioxide: surfactants, polymers and biomaterials. J Mater Chem 14 11 (2004) 1663-1678
Cooper A.I. Polymer synthesis and processing using supercritical carbon dioxide. J Mater Chem 10 2 (2000) 207-234
Canelas D.A., and DeSimone J.M. Polymerizations in liquid and supercritical carbon dioxide. Adv Polym Sci 133 (1997) 103-140
Odell P.G., and Hamer G.K. Living free radical polymerizations in supercritical carbon dioxide. Polym Mater Sci Eng 74 (1996) 404-405
Ryan J., Aldabbagh F., Zutterlund P., and Okubo M. First nitroxide-mediated free radical dispersion polymerizations of styrene in supercritical carbon dioxide. Polymer 46 23 (2005) 9769-9777
Arita T., Beuermann S., Buback M., and Vana P. Reversible addition fragmentation chain transfer (RAFT) polymerization of styrene in fluid CO2. e-Polymers (2004)
Thurecht K.J., Gregory A.M., Villarroya S., Zhou J., Heise A., and Howdle S.M. Simultaneous enzymatic ring opening polymerization and RAFT-mediated polymerization in supercritical CO2. Chem Commun 42 (2006) 4383-4385
Xia J., Johnson T., Gaynor S.G., Matyjaszewski K., and DeSimone J.M. Atom transfer radical polymerization in supercritical carbon dioxide. Macromolecules 32 15 (1999) 4802-4805
Minami H., Kagawa Y., Kuwahara S., Shigematsu J., Fujii S., and Okubo M. Dispersion atom transfer radical polymerization of methyl methacrylate with bromo-terminated poly(dimethylsiloxane) in supercritical carbon dioxide. Des Monomers Polym 7 6 (2004) 553-562
Villarroya S., Zhou J., Duxbury C.J., Heise A., and Howdle S.M. Synthesis of semifluorinated block copolymers containing poly(ε-caprolactone) by the combination of ATRP and enzymatic ROP in scCO2. Macromolecules 39 2 (2006) 633-640
Villarroya S., Zhou J., Thurecht K.J., and Howdle S.M. Synthesis of graft copolymers by the combination of ATRP and enzymatic ROP in scCO2. Macromolecules 39 26 (2006) 9080-9086
McHugh M.A., and Krukonis V.J. Supercritical fluid extraction - principles and practice (1986), Butterworths, Boston
Tuminello W.H., Dee G.T., and McHugh M.A. Dissolving perfluoropolymers in supercritical carbon dioxide. Macromolecules 28 (1995) 1506-1510
Desimone J.M., Guan Z., and Elsbernd C.L. Synthesis of fluoropolymers in supercritical carbon dioxide. Science 257 (1992) 945-947
Hoefling T.A., Newman D.A., Enick R.M., and Beckman E. Effect of structure on the cloud-point curves of silicone-based amphiphiles in supercritical carbon dioxide. J Supercrit Fluids 6 3 (1993) 165-171
Grignard B., Calberg C., Jérôme C., Detrembleur C., and Jérôme R. Controlled synthesis of carboxylic acid end-capped poly(heptadecafluorodecyl acrylate) and copolymers with 2-hydroxyethyl acrylate. J Polym Sci: Part A, Polym Chem 45 8 (2007) 1499-1506
Postma A., Davis T.P., Moad G., and O'Shea M.S. Thermolysis of RAFT-Synthesized Polymers. A convenient method for trithiocarbonate group elimination. Macromolecules 38 13 (2005) 5371-5374
Mayadunne R.T.A., Jeffery J., Moad G., and Rizzardo E. Living free radical polymerization with reversible addition-fragmentation chain transfer (RAFT polymerization): approaches to star polymers. Macromolecules 36 5 (2003) 1505-1513
Mayadunne R.T.A., Rizzardo E., Chiefari J., Krstina J., Moad G., Postma A., et al. Living polymers by the use of trithiocarbonates as reversible addition-fragmentation chain transfer (RAFT) agents. ABA triblock copolymers by radical polymerization in two steps. Macromolecules 33 2 (2000) 243-245
Wang Z., He J., Tao Y., Yang L., Jiang H.W.Z., He J., et al. Controlled chain branching by RAFT-based radical polymerization. Macromolecules 36 (2003) 7446-7452
Favier A., Ladaviere C., Charreyre M.-T., and Pichot C. MALDI-TOF MS investigation of the RAFT polymerization of a water-soluble acrylamide derivative. Macromolecules 37 6 (2004) 2026-2034
Ma Z., and Lacroix-Desmazes P. Synthesis of hydrophilic/CO2-philic poly(ethylene oxide)-b-poly(1,1,2,2-tetrahydroperfluorodecyl acrylate) block copolymers via controlled/living radical polymerizations and their properties in liquid and supercritical CO2. J Polym Sci: Part A Polym Chem 42 10 (2004) 2405-2415
Kleij A.W., Gossage R.A., Gebbink R.K., Brinkmann N., Reijerse E.J., Kragl U., et al. A "dendritic effect" in homogeneous catalysis with carbosilane supported arylnickel(II) catalysts: observation of active-site proximity effects in atom transfer radical addition. J Am Chem Soc 122 49 (2000) 12112-12124
Grignard B, Jerome C, Calberg C, Wang W, Howdle SM, Jerome R, et al. Copper bromide complexed by fluorinated macro-ligands: towards microspheres by ATRP of vinyl monomers in scCO2. Chem Commun 2008. doi:10.1039/b716208a.
Similar publications
Sorry the service is unavailable at the moment. Please try again later.
This website uses cookies to improve user experience. Read more
Save & Close
Accept all
Decline all
Show detailsHide details
Cookie declaration
About cookies
Strictly necessary
Performance
Strictly necessary cookies allow core website functionality such as user login and account management. The website cannot be used properly without strictly necessary cookies.
This cookie is used by Cookie-Script.com service to remember visitor cookie consent preferences. It is necessary for Cookie-Script.com cookie banner to work properly.
Performance cookies are used to see how visitors use the website, eg. analytics cookies. Those cookies cannot be used to directly identify a certain visitor.
Used to store the attribution information, the referrer initially used to visit the website
Cookies are small text files that are placed on your computer by websites that you visit. Websites use cookies to help users navigate efficiently and perform certain functions. Cookies that are required for the website to operate properly are allowed to be set without your permission. All other cookies need to be approved before they can be set in the browser.
You can change your consent to cookie usage at any time on our Privacy Policy page.