Synthesis of new ‘Saccharide polymers’ from unsaturated monosaccharides

Buchholz, Klaus; Warn, S.; Skeries, Bernhard; Wick, Stefan; Yaacoub, Emile-Joseph

doi:10.1002/9783527614899.ch9

Cited by 4 publications

(3 citation statements)

References 18 publications

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“…Acrylate as well as styrene derivatives of carbohydrates have been prepared by various acylation or glycosidation reactions for obtaining hydrophilic polymeric stationary phases for analytic purposes, as well as for designing original hydrosoluble carriers and biocompatible adhesives for biomedical applications. [3][4][5] However, for a better respect of the green chemistry principles, 6 conversion of the selected biosourced precursors into target monomers should be preferentially achieved with particular attention to atom economy. Accordingly, unsaturations can be formed by elimination reactions achievable at numerous positions of common carbohydrates.…”

Section: Introductionmentioning

confidence: 99%

Reactivity of Vinyl Ethers and Vinyl Ribosides in UV-Initiated Free Radical Copolymerization with Acceptor Monomers

2010

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The reactivity of various vinyl ethers and vinyloxy derivatives of ribose in the presence of diethyl fumarate or diethyl maleate was investigated for evaluating the potential of donor-acceptor-type copolymerization applied to unsaturated monomers derived from renewable feedstock. The photochemically induced polymerization of model monomer blends in the bulk state was monitored by infrared spectroscopy. The method allowed us to examine the influence of monomer pair structure on the kinetic profiles. The simultaneous consumption of both monomers was observed, supporting an alternating copolymerization mechanism. A lower reactivity of the blends containing maleates compared with fumarates was confirmed. The obtained kinetic data revealed a general correlation between the initial polymerization rate and the Hansen parameter δ(H) associated with the H-bonding aptitude of the donor monomer.

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Section: Introductionmentioning

confidence: 99%

Reactivity of Vinyl Ethers and Vinyl Ribosides in UV-Initiated Free Radical Copolymerization with Acceptor Monomers

2010

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“…A difficult task was to introduce sugars into main carbon chain of the polymer. We succeeded in the synthesis of such saccharide polymers, as they are termed, early in the nineties 15–21. A variety of polymerizable saccharide monomers have been synthesized from sources like glucose, fructose etc.…”

Section: Introductionmentioning

confidence: 99%

“…A variety of polymerizable saccharide monomers have been synthesized from sources like glucose, fructose etc. and have been shown to undergo radical copolymerization with a wide range of commercial comonomers 13–21. An ongoing problem was to find an easy, convenient way of synthesis of saccharide monomers, which is essential for scale up and utilization.…”

Section: Introductionmentioning

confidence: 99%

Saccharide Polymers, 5

Glümer

Skeries

Buchholz

2004

Macro Chemistry & Physics

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Summary: New “saccharide polymers” were synthesized via free radical polymerization. The saccharide compounds in copolymerisation reactions were 2,4,6‐tri‐O‐acetyl‐3‐deoxy‐D‐erythro‐hex‐2‐enono‐1,5‐lactone (1), (Ac‐GEL 1) and 2,4,6‐tri‐O‐benzoyl‐3‐deoxy‐D‐erythro‐hex‐2‐enono‐1,5‐lactone (2), (Bz‐GEL 2). These sugar monomers are easily obtained with high yield in a one step reaction from glucono‐δ‐lactone. They have a pyranoid structure containing an endocyclic double bond and they are electron acceptor compounds. Copolymerization reactions were carried out in solution and in substance. Copolymers with different sugar contents and low as well as high molecular weights were obtained. The structures and the compositions of the soluble saccharide polymers were established by elemental analysis, polarimetry, FTIR spectroscopy, 1H and 13C NMR spectroscopy. Some characteristic properties, e.g., molecular weight, optical rotation and copolymerization parameters are reported.

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Erneuerbare Rohstoffe biotechnologischen oder pflanzlichen Ursprungs für die Oberflächenbehandlung

Friebel

Deppe

2009

Chemie Ingenieur Technik

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Der wesentliche Beweggrund Beschichtungen auf Basis nachwachsender Rohstoffe (Nawaro) zu entwickeln und zu verwenden ist nach wie vor die Erwartung, dass diese Produkte in Zukunft durch die stetig steigenden Erdölpreise ökonomischer werden. Auch die Endlichkeit des Erdöls und die damit verbundene hohe Abhängigkeit gegenüber den OPEC-Staaten sind Gründe, alternative Ressourcen zur Herstellung von Beschichtungsstoffen zu finden. Dieser Beitrag soll den derzeitigen Stand der Technik und auch neue Trends der stofflichen Nutzung von nachwachsenden Rohstoffen speziell für die Lackindustrie näher beleuchten. Es werden Möglichkeiten aufgezeigt, die Nawaro bei der Synthese von Lackharzen bieten. Dabei werden die Schwerpunkte auf die Chemie der pflanzlichen Öle und Saccharide gelegt und dabei die klassische Chemie und auch neuere Methoden - wie die enzymatische Katalyse oder die Industrielle Biotechnologie - aufgeführt, die zur Herstellung von Bindemitteln für dauerhafte Industrie- und Bautenlacke sowie Druckfarben verwendet werden können. Spezielle Anwendungen, wie z. B. Food-Coatings, medizinische Beschichtungsstoffe und biologisch abbaubare Beschichtungen, werden nicht berücksichtigt

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Synthesis of new ‘Saccharide polymers’ from unsaturated monosaccharides

Cited by 4 publications

References 18 publications

Reactivity of Vinyl Ethers and Vinyl Ribosides in UV-Initiated Free Radical Copolymerization with Acceptor Monomers

Reactivity of Vinyl Ethers and Vinyl Ribosides in UV-Initiated Free Radical Copolymerization with Acceptor Monomers

Saccharide Polymers, 5

Erneuerbare Rohstoffe biotechnologischen oder pflanzlichen Ursprungs für die Oberflächenbehandlung

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