iminoéthers-1 3 cycliques : chimie et applications dans le domaine des additifs pétroliers et des matériaux organiques cyclic 1,3-iminoethers: chemistry and applications in the field of petroleum additives and organic materials
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ID: 247743
2006
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Abstract
Cet article est consacré aux iminoéthers-1,3 cycliques les plus courants : les oxazines-1,3 et oxazolines-1,3. La première partie rappelle les synthèses de ces composés et quelques aspects récents de leur chimie : réactions d'hydrolyse, réactions de déprotonation avec ouverture de cycle, réactions des organométalliques, réactions d'addition des nucléophiles en positions 2 et 5, des sels d'iminoéthers correspondants, propriétés complexantes vis-à-vis des métaux, réactions d'aminolyse et formation de structures tensioactives, enfin polymérisations et copolymérisations cationiques. La seconde partie est consacrée à l'étude des travaux qui traitent des applications. En ce qui concerne le domaine des additifs pétroliers, on s'intéresse à la stabilité du cycle oxazoline et à son caractère polaire. Les dérivés tensioactifs dérivés d'oxazoline portant des chaînes hydrocarbonées ont été revendiqués comme additifs dispersants et multifonctionnels pour les carburants et les lubrifiants. De nombreuses formulations (dispersants, antioxydants antirouilles, antiusures, extrême pressions, réducteurs de frictions. . . ) ont été proposées. Certains dérivés d'hydroxyméthyl oxazolines présentent des propriétés lubrifiantes et d'autres ont un intérêt dans les formulations de boues de forage. En ce qui concerne le domaine des matériaux, on s'intéresse à la réactivité du cycle oxazoline pour réaliser soit des extensions de chaînes des thermoplastiques, soit des réticulations pour des applications de peintures et revêtements. Les homopolymères d'oxazoline qui ont un caractère polaire très marqué peuvent trouver des applications comme promoteur d'adhésion, ou tensioactifs pour les polymérisations en émulsion. Enfin, l'utilisation d'oxazolines stables a été revendiquée dans des formulations de vernis d'émaillage.
This article deals with the most common cyclic 1,3-iminoethers, i. e. 1,3-oxazines and 1,3-oxazolines. The first part reviews the syntheses of these compounds and some recent aspects of their chemistry, i. e. hydrolysis reactions, deprotonation reactions with ring opening, reactions with organometallic compounds, regioselective nucleophilic reactions on the corresponding iminoether salts, complexing properties with the metallic salts, aminolysis reactions leading to surfactant structures, and cationic polymerizations and copolymerizations. The second part is devoted to a survey of research dealing with applications. Concerning the field of petroleum additives, many products have been synthetized having in mind the stability of the oxazoline ring and its polar nature. Surfactant derivates coming from oxazoline having hydrocarbon chains have been claimed as dispersant and multifunctional additives for fuels and lubricants. Many multifunctional formulations (dispersant, antioxidant, antirust, antiwear, extreme pressure, friction reducing, etc. ) have been proposed. Some hydroxymethyl-oxazoline derivatives have lubricant properties, and others are of interest for drilling mud formulations. Concerning the field of materials, interest is being shown in the reactivity of the oxazoline ring for creating either chain extensions of thermoplastics or cross-linking for applications in paints and coatings. Oxazoline homopolymers, which have a very polar structure can be used as adhesion promoters or surfactants for polymerizations in emulsion. The use of stable oxazolines has also been claimed in enameling-varnish formulations for the coating of copper wires.
This article deals with the most common cyclic 1,3-iminoethers, i. e. 1,3-oxazines and 1,3-oxazolines. The first part reviews the syntheses of these compounds and some recent aspects of their chemistry, i. e. hydrolysis reactions, deprotonation reactions with ring opening, reactions with organometallic compounds, regioselective nucleophilic reactions on the corresponding iminoether salts, complexing properties with the metallic salts, aminolysis reactions leading to surfactant structures, and cationic polymerizations and copolymerizations. The second part is devoted to a survey of research dealing with applications. Concerning the field of petroleum additives, many products have been synthetized having in mind the stability of the oxazoline ring and its polar nature. Surfactant derivates coming from oxazoline having hydrocarbon chains have been claimed as dispersant and multifunctional additives for fuels and lubricants. Many multifunctional formulations (dispersant, antioxidant, antirust, antiwear, extreme pressure, friction reducing, etc. ) have been proposed. Some hydroxymethyl-oxazoline derivatives have lubricant properties, and others are of interest for drilling mud formulations. Concerning the field of materials, interest is being shown in the reactivity of the oxazoline ring for creating either chain extensions of thermoplastics or cross-linking for applications in paints and coatings. Oxazoline homopolymers, which have a very polar structure can be used as adhesion promoters or surfactants for polymerizations in emulsion. The use of stable oxazolines has also been claimed in enameling-varnish formulations for the coating of copper wires.
| Reference Key |
p.2006oiliminothers-1
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|---|---|
| Authors | ;Le Perchec P.;Sillion B.;Salle R. |
| Journal | addiction (abingdon, england) |
| Year | 2006 |
| DOI |
10.2516/ogst:1986017
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| URL | |
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