Reactivity of 3 isopropenyl-α,α-dimethyl-benzylisocyanate with amines, phenols, thiols and oximes in diluted aqueous–organic media: the water-promoted effect

Vandenabeele-Trambouze, O.; Mion, L.; Garrelly, Laurent; Commeyras, A.

doi:10.1016/s1093-0191(00)00070-8

Cited by 6 publications

(1 citation statement)

References 29 publications

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“…They considered the fact that monomeric alcohols are 1000 times less reactive than trimer forms. The authors conjectured that the lack of reactivity in the concentration range (2 × 10 −1 -2 × 10 −4 M) is due to a loss of catalytic effect (due to a lack of nucleophile polymers) in addition to low isocyanate reactivity [33]. However, as a consequence, the addition of the isocyanate, the alcohol and amine moiety took place, resulting in bis-urea or bis-urethane compounds b and c, shown in Figure 5 [34].…”

Section: Synthesis Of Polyureasmentioning

confidence: 99%

Polyureas Versatile Polymers for New Academic and Technological Applications

et al. 2021

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Polyureas (PURs) are a competitive polymer to their analogs, polyurethanes (PUs). Whereas PUs’ main functional group is carbamate (urethane), PURs contain urea. In this revision, a comprehensive overview of PUR properties, from synthesis to technical applications, is displayed. Preparative routes that can be used to obtain PURs using diisocianates or harmless reagents such as CO2 and NH3 are explained, and aterials, urea monomers and PURs are discussed; PUR copolymers are included in this discussion as well. Bulk to soft components of PUR, as well as porous materials and meso, micro or nanomaterials are evaluated. Topics of this paper include the general properties of aliphatic and aromatic PUR, followed by practical synthetic pathways, catalyst uses, aggregation, sol–gel formation and mechanical aspects.

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Section: Synthesis Of Polyureasmentioning

confidence: 99%

Polyureas Versatile Polymers for New Academic and Technological Applications

et al. 2021

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Antibodies directed against L and D isovaline using a chemical derivatizing reagent for the measurement of their enantiomeric ratio in extraterrestrial samples: First step–production and characterization of antibodies

Vandenabeele-Trambouze¹,

Geffard

Bodet

et al. 2002

Chirality

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Determining the enantiomeric ratio of amino acids in meteorites requires very sensitive and precise measurements. In this study, an immunochemical approach, combined with new chemical derivatizing agents, was investigated for the measurement of the enantiomeric ratio of isovaline. In the initial step, L and D isovaline were derivatized with epsilon-benzyloxycarbonyl-L-lysine-(t-butyl ester)-chloroethylnitrosourea (Z-L-Lys-(OtBu)-CENU). The Z group was hydrolyzed and the resulting isovaline derivatives (L-Lys(OtBu)-L-isovaline and L-Lys(OtBu)-D-isovaline) were conjugated with protein using glutaraldehyde and reduced with sodium borohydride. Rabbits were immunized with the immunogenic conjugates thus obtained. Antibodies were characterized using many compounds, both derivatized and underivatized, in competitive ELISA tests. These competition experiments performed enabled us to establish the following results: 1) unconjugated L-Lys(OtBu)-L-isovaline and L-Lys(OtBu)-D-isovaline were poorly recognized; 2) all related L-Lys(OtBu)-alpha-hydrogenated amino acids (L and D) were not recognized at all, which eliminates the possibility of the measurements being distorted by contamination; 3) only conjugated L-Lys(OtBu)-alpha-amino-isobutyric acid (AIB) was recognized by the antibody, 4) the enantiomeric discrimination of L and D isovaline through their derivatives (diastereoisomeric L-Lys(OtBu)-L-isovaline and L-Lys(OtBu)-D-isovaline) was in accordance with the measurement of their enantiomeric ratio. Immunopurification was shown to enhance antibody specificity. The strategy employed shows potential for the quantification of meteoritic amino acids.

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“Clickable” polymers via a combination of RAFT polymerization and isocyanate chemistry

Moraes

Maschmeyer

Perrier

2011

J. Polym. Sci. A Polym. Chem.

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We describe a facile, one‐pot, two‐step polymerization towards synthesizing block co‐polymers bearing reactive isocyanate functional groups. Reversible addition fragmentation chain transfer (RAFT) polymerization is used to mediate the co‐polymerization of isocyanate‐bearing monomers dimethyl meta‐isopropenyl benzyl isocyanate (TMI) and 2‐isocyanatoethyl methacrylate (ICEMA) with styrene and methyl methacrylate (MMA), respectively. ICEMA was incorporated into the polymer at a faster rate than TMI and its unhindered isocyanate group was found to be more reactive than the hindered isocyanate group of TMI. Both the TMI/styrene and the MMA/ICEMA systems maintain the reactivity of the isocyanate functionality, which was exploited by attaching representative hydroxyl‐bearing small and large molecules as well as solid substrates to the block co‐polymers. Thus, we demonstrate the versatility of the block co‐polymer system as a basis for forming branched polymers or as grafts for a solid substrate. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

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Reactivity of 3 isopropenyl-α,α-dimethyl-benzylisocyanate with amines, phenols, thiols and oximes in diluted aqueous–organic media: the water-promoted effect

Cited by 6 publications

References 29 publications

Polyureas Versatile Polymers for New Academic and Technological Applications

Polyureas Versatile Polymers for New Academic and Technological Applications

Antibodies directed against L and D isovaline using a chemical derivatizing reagent for the measurement of their enantiomeric ratio in extraterrestrial samples: First step–production and characterization of antibodies

“Clickable” polymers via a combination of RAFT polymerization and isocyanate chemistry

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