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1. Synthesis of natural rubber-based telechelic cis-1,4-polyisoprenes and their use to prepare block copolymers via RAFT polymerization

Author

Jean‐Claude Soutif, Nitinart Saetung, Irène Campistron, Jean Francois Pilard, Sagrario Pascual, Laurent Fontaine, Unité de chimie organique moléculaire et macromoléculaire (UCO2M), and Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
Polymers and Plastics, Radical polymerization, General Physics and Astronomy, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Reductive amination, polyisoprene reversible addition fragmentation chaintransfer (RAFT), Polymer chemistry, Materials Chemistry, Copolymer, Reversible addition−fragmentation chain-transfer polymerization, ComputingMilieux_MISCELLANEOUS, Telechelic polymer, Chemistry, Organic Chemistry, Chain transfer, oxidative degradation, 021001 nanoscience & nanotechnology, 0104 chemical sciences, End-group, [CHIM.POLY]Chemical Sciences/Polymers, telechelics, Polymerization, 0210 nano-technology, naturel rubber
Abstract

A new trithiocarbonate functionalized cis-1,4-polyisoprene was obtained from oxidative degradation of natural rubber followed by reductive amination and amidation. The structure of the resulting functionalized cis-1,4-polyisoprene was confirmed by a combination of 1H NMR spectroscopy, 13C NMR spectroscopy, MALDI-TOF mass spectrometry and FTIR spectroscopy. 1H NMR spectroscopy showed that the trithiocarbonate functionality was equal to one. The well-defined trithiocarbonyl-end functionalized cis-1,4-polyisoprene was used as a macromolecular chain transfer agent (macroCTA) to mediate the RAFT polymerization of t-BA using AIBN as the initiator ([t-BA]0/[macroCTA]0/[AIBN]0 = 250/1/0.2) in toluene at 60 °C. The resulting PI-b-P(t-BA) diblock copolymer presents an unimodal SEC trace shifted toward higher molecular weight in comparison with the SEC trace of the macroCTA, indicating that the polymerization of the second block is effective. The characteristics of the copolymer were determined by SEC ( M ¯ n = 26,000 g mol−1, PDI = 1.76) and 1H NMR spectroscopy ( DP ¯ n (PI) = 62 and DP ¯ n (P(t-BA)) = 87).

Published
2011
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2. Use of telechelic cis-1,4-polyisoprene cationomers in the synthesis of antibacterial ionic polyurethanes and copolyurethanes bearing ammonium groups

Author

Albert Laguerre, Jean-François Pilard, Thierry Jouenne, Irène Campistron, Claude Bunel, Nasreddine Kébir, Polymères Biopolymères Surfaces (PBS), Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut de Chimie du CNRS (INC)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS), Unité de chimie organique moléculaire et macromoléculaire (UCO2M), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut des Molécules et Matériaux du Mans (IMMM), Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Polymères, biopolymères, membranes (PBM), Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU), and Bonnier, Maryvonne

Subjects
[CHIM.POLY] Chemical Sciences/Polymers, Materials science, Chemical structure, Polyurethanes, Biophysics, Ionic bonding, Biocompatible Materials, Bioengineering, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Biomaterials, Contact angle, chemistry.chemical_compound, Hemiterpenes, Natural rubber, Cations, Pentanes, Materials Testing, Polymer chemistry, Butadienes, Staphylococcus epidermidis, medicine, [CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, technology, industry, and agriculture, Dynamic mechanical analysis, Polymer, 021001 nanoscience & nanotechnology, 6. Clean water, Anti-Bacterial Agents, 0104 chemical sciences, Disinfection, Quaternary Ammonium Compounds, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, Mechanics of Materials, visual_art, Pseudomonas aeruginosa, Ceramics and Composites, visual_art.visual_art_medium, Swelling, medicine.symptom, Isophorone diisocyanate, 0210 nano-technology
Abstract

New crosslinked ionic polyurethanes and copolyurethanes were yielded by reaction of telechelic cis-1,4-oligoisoprenes, bearing a variable number of ammonium and hydroxy groups, with isocyanurate of isophorone diisocyanate (I-IPDI). Aiming for a comparative study, polyurethane elastomers based on non-ionic telechelic oligomers were also synthesized. Thermo-mechanical behavior and crosslinking density of these three families of materials were investigated by DMTA and swelling test, respectively. Surface properties were examined by static contact angle measurements and AFM imaging. The bactericidal activity of the polymers was investigated by enumerating living Pseudomonas aeruginosa on material surfaces and on water suspensions. The number of attached living bacteria was found to depend on the chemical structure of the material and on the contact time between the microorganisms and the surface. An exclusive bactericidal activity was obtained with the ionic copolyurethane family. Materials with weak crosslinking density were found to release bactericidal moieties. The abilities of the polymers to prevent bacterial growth were examined through zone of inhibition experiments against P. aeruginosa, which shown a bacteriostatical effect for each synthesized material. These experiments were not sufficiently sensitive to detect the leaching of bactericidal moieties from the materials with weak crosslinking density. When the zone of inhibition experiments was performed on more sensitive bacteria, namely Staphylococcus epidermidis, the leaching of bactericidal moieties as well as bacteriostatic effect was detected. This work demonstrates the potentiality for making functional biomaterials from natural rubber, a renewable resource.

Published
2007
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3. Metathetic alkenolysis of unsaturated units in polymers and copolymers––application to the synthesis of epoxy-functionalized oligomers and organic compounds

Author

Albert Laguerre, Paragkumar Nathalal Thanki, Irène Campistron, Raj Pal Singh, and Danièle Reyx

Subjects
chemistry.chemical_classification, Polymers and Plastics, Double bond, Depolymerization, Alkene, Organic Chemistry, General Physics and Astronomy, chemistry.chemical_element, Oligomer, Ruthenium, chemistry.chemical_compound, chemistry, Polymer chemistry, Materials Chemistry, Copolymer, Organic chemistry, Phosphine, Cis–trans isomerism
Abstract

Depolymerization of 20% epoxidized cis-1,4-polybutadiene was carried out through alkenolysis of the butadiene repeat units (B) using 4-octene as depolymerizing agent (DA) and bis(tricyclohexyl phosphine)benzylidene ruthenium (IV) dichloride (1) as catalyst. The average molecular weight of the depolymerization products was determined by NMR, and SEC, and their constituents were identified by GC MS. Cis-4-octene was found more efficient in performing the depolymerization as compared to its trans isomer. Besides dodeca-4,8-diene and hexadeca-4,8,12-triene, 2,3-di[3-heptenyl]-oxirane with a cis oxirane configuration was clearly characterized. Beside the DA to B mole ratio, the catalyst to double bond mole ratio was observed as the major factor controlling the molecular weight of the depolymerization products and the 2,3-di[3-heptenyl]-oxirane yields.

Published
2004
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4. Continuous automated measurement of carbon dioxide produced by microorganisms in aerobic conditions: application to proteic film biodegradation

Author

Marc Laulier, Sandra Lefaux, Vincent Leignel, Ludovic Benguigui, Irène Campistron, Annick Manceau, Gérard Tremblin, and Albert Laguerre

Subjects
Chemistry, General Chemical Engineering, Microorganism, Mineralogy, Biomass, General Chemistry, Straw, Biodegradation, Pulp and paper industry, chemistry.chemical_compound, Activated sludge, Carbon dioxide, Bioreactor, Aerobic digestion
Abstract

A new automated set-up based on the original Sturm test was developed for determining the biodegradability of proteic mulching films. This method is based on the measurement of released (respiratory metabolism of microorganisms) carbon dioxide to determine film biodegradability. Maintenance of constant aerobic conditions in thermoregulated bioreactors and continuous measurement of released CO2 with an infrared differential gas analyser were the main advantages of this set-up. It was verified with a plasticised proteic film that soil extracts could be used as microbial sources instead of activated sludge that was usually used in laboratory biodegradation tests. To cite this article: S. Lefaux et al., C. R. Chimie 7 (2003).

Published
2004
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5. Effet d’extrémité de chaı̂ne dans l’oxydation du caoutchouc naturel accélérée par la phénylhydrazine

Author

Irène Campistron, Souad Fkih Tétouani, Azeddine El Hamdaoui, and Danièle Reyx

Subjects
Reaction mechanism, Polymers and Plastics, Oxidative degradation, Depolymerization, Chemistry, Organic Chemistry, General Physics and Astronomy, Natural rubber, Liquid rubber, visual_art, Polymer chemistry, Materials Chemistry, visual_art.visual_art_medium, Chemical solution, Gas liquid reaction
Abstract

Resume Un caoutchouc synthetique (CK) et deux caoutchoucs naturels liquides (CF et Cf) ont ete selectionnes en fonction de leur teneur en extremites phenylcetone (EP) et methylcetone (EM). L’oxydation acceleree est conduite par barbotage d’oxygene dans de solutions (benzene) de concentration constante en polyisoprenes (10 g l−1) et de concentration variable en phenylhydrazine (20 mmol l−1

Published
1999
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6. Use of new hydroxytelechelic cis-1,4-polyisoprene (HTPI) in the synthesis of polyurethanes (PUs): Influence of isocyanate and chain extender natureand their equivalent ratios on the mechanical and thermal properties of PUs

Author

Jean-François Pilard, Jean-Pierre Couvercelle, Claude Bunel, Albert Laguerre, Irène Campistron, Nasreddine Kébir, Polymères Biopolymères Surfaces (PBS), Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université Le Havre Normandie (ULH), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU), Unité de chimie organique moléculaire et macromoléculaire (UCO2M), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS), Institut des Molécules et Matériaux du Mans (IMMM), Centre National de la Recherche Scientifique (CNRS)-Le Mans Université (UM), Polymères, biopolymères, membranes (PBM), Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université de Rouen Normandie (UNIROUEN), Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon] (ICMUB), Université de Bourgogne (UB)-Centre National de la Recherche Scientifique (CNRS), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut de Chimie du CNRS (INC)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Université de Bourgogne (UB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Unité de chimie organique moléculaire et macromoléculaire ( UCO2M ), Le Mans Université ( UM ) -Centre National de la Recherche Scientifique ( CNRS ), Polymères, biopolymères, membranes ( PBM ), Centre National de la Recherche Scientifique ( CNRS ) -Institut national des sciences appliquées Rouen Normandie ( INSA Rouen Normandie ), Normandie Université ( NU ) -Normandie Université ( NU ) -Université de Rouen Normandie ( UNIROUEN ), Normandie Université ( NU ), Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon] ( ICMUB ), and Université de Bourgogne ( UB ) -Centre National de la Recherche Scientifique ( CNRS )

Subjects
Thermogravimetric analysis, Materials science, synthesis, Polymers and Plastics, General Chemical Engineering, polyurethanes, 02 engineering and technology, law.invention, thermoplastic-elastomers, chemistry.chemical_compound, Chain (algebraic topology), law, Thermal, Polymer chemistry, [CHIM]Chemical Sciences, Thermal stability, Physical and Theoretical Chemistry, Thermoplastic elastomer, ComputingMilieux_MISCELLANEOUS, 020502 materials, Extender, Dynamic mechanical analysis, 021001 nanoscience & nanotechnology, Isocyanate, [ CHIM.POLY ] Chemical Sciences/Polymers, [CHIM.POLY]Chemical Sciences/Polymers, 0205 materials engineering, chemistry, 0210 nano-technology
Abstract

New segmented polyurethanes (thermoplastic-elastomers) based on previously described hydroxytelechelic cis-1,4-polyisoprene (HTPI), miscellaneous isocyanates and chain extenders at various equivalent ratios were prepared by the classical one-shot method. The influence of the nature of isocyanate and chain extender, as well as their equivalent ratios, on the mechanical and thermal materials behavior was investigated. Thus, a comparative assessment of material properties was performed. Microphase separation of hard and soft segments was observed by DMTA, DSC and AFM. Moreover, according to Thermogravimetric Analysis (TGA), linear relationships depending on the isocyanate and chain extender nature were found between the weight loss (%) and the percentages of hard segments. A classification of thermal stability in terms of weight loss was established. With the aim of a thermo-mechanical comparative study, polyurethane elastomers based on HTPI and isocyanates without chain extender, were also synthesized.

Published
2006
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7. Ring-opening metathesis polymerization (ROMP) of isomerically pure functional monomers and acyclic diene metathesis depolymerization (retro-ADMET) of functionalized polyalkenamers

Author

Laurent Fontaine, Irène Campistron, Danièle Reyx, Véronique Montembault, Vincent Lapinte, Laboratoire de Chimie Organique Macromoléculaire [Université du Maine] (LCOM), and Université du Maine [Le Mans - Laval]

Subjects
Diene, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Process Chemistry and Technology, ROMP, 010402 general chemistry, Metathesis, 01 natural sciences, Ring-opening polymerization, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, [CHIM.POLY]Chemical Sciences/Polymers, Polymer chemistry, Ring-opening metathesis polymerisation, Organic chemistry, Physical and Theoretical Chemistry, Functional polymers, Norbornene, Acyclic diene metathesis
Abstract

ROMP and retro-acyclic diene metathesis (ADMET) were used for the synthesis of new functional polymers and functional oligomers, respectively. Purely exo and enantiomerically pure norbornene and 7-oxanorbornene derivatives were prepared using stereospecific synthesis, effective fractionation and high yield condensation reactions. Successful ROMPs of those monomers were performed using either the new carbenic Schrock’s or Grubb’s catalysts or in some cases a classical bicomponent catalyst. New functional polymers such as optically active poly(norbornene-2-carboxylic acid), reactive poly(norbornene-2-azlactone), and side-chain liquid crystal polyoxanorbornenes were fully characterized. On the other hand, successful depolymerizations of 1,4-polyisoprene and of epoxidized 1,4-polybutadiene via cross-metathesis with 4-octene were performed using a stabilized bicomponent catalyst and the Grubb’s catalyst, respectively. Conditions for the controlled synthesis of epoxidized oligobutadienes and of epoxydienic monomers via retro-ADMET were clearly defined. © 2002 Elsevier Science B.V. All rights reserved.

Published
2002
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