Synthesis of Simple Oxetanes Carrying Reactive 2-Substituents

Fitton, A. O.; Hill, J.O.; Jane, David E.; Millar, Russell B.

doi:10.1055/s-1987-28203

Cited by 222 publications

(210 citation statements)

References 0 publications

Supporting

Mentioning

202

Contrasting

Unclassified

Order By: Relevance

“…Ethoxyethylprotected glycidyl ether was synthesized according to the published procedure by Fitton et al [16] AGE (Sigma-Aldrich, 99%), tBuGE (SigmaAldrich, >99%), and the synthesized EEGE were stored over CaH 2 and distilled in vacuo over molecular sieve before use to remove traces of water. Styrene (Sigma-Aldrich, ReagentPlus, ≥99%) was purified before use by passing through neutral Al 2 O 3 .…”

Section: Methodsmentioning

confidence: 99%

Polyglycerol Surfmers and Surfactants for Direct and Inverse Miniemulsion

Wald

Simon

Dietz

et al. 2017

Macromolecular Bioscience

View full text Add to dashboard Cite

studied as promising surfactants for emulsions. [10] Furthermore, vinyl-terminated polyglycerols were used as surfmers to synthesize stable polystyrene (PS) microspheres for medical diagnostics for possible postfunctionalization with proteins. [11,12] Hyperbranched and linear surfmers based on polyglycerols were additionally used to generate stable PS nanoparticles. [13] However, for the miniemulsion approach only less multifunctional PG-based surfactants or surfmers are known.Here, we use the versatility of the anionic polymerization of glycidyl ethers to prepare a series of multifunctional (additional OH-groups or polymerizable CC-groups) surfactants with adjustable hydrophiliclipophilic balance (HLB) that allows the stabilization of direct (oil-in-water) or inverse (water-in-oil) (mini)emulsions or can be used simultaneously for both systems.Two known orthogonal protection strategies, reported by Möller and coworkers, [14] were used to synthesize linear completely poly glycerol-based block copolymers as surfactants or surfmers for direct, inverse, or both types of miniemulsions (Scheme 1). The orthogonal-protected block copolymers were generated by anionic ring-opening polymerization in bulk using ethoxyethyl glycidyl ether (EEGE) and allyl glycidyl ether (AGE) or tert-butyl glycidyl ether (tBuGE) with defined block length ratios to tune their HLB. After acidic hydrolysis of the acetal groups, the water-soluble allyl-functionalized PG block copolymers were established as surfmers in the radical miniemulsion poly merization of styrene to generate polystyrene nanoparticles with decreased protein adsorption behavior due to incorporated PG surfactants (Scheme 1). In addition, oil-soluble allyl-functionalized block copolymers were introduced as surfmers to produce polyurea/urethane nanocapsules by interfacial polyaddition reactions of hydroxyethyl starch (HES) with toluene diisocyanate (TDI) (Scheme 1). [15] Furthermore, the allyl-protection groups on the polyurethane nanocarrier surface were utilized for surface functionalization by thiol-ene addition in water. For this purpose, the nanocarriers were transferred into water including a tert-butyl-protected poly glycerol block copoly mer. The tert-butyl-protected polyglycerol block copolymers were applied as surfactant to generate polystyrene nanoparticles in direct miniemulsions for comparison with the allyl-protected surfmer and in inverse miniemulsions to produce stable poly(hydroxyethyl methacrylate) (PHEMA)

show abstract

Section: Methodsmentioning

confidence: 99%

Polyglycerol Surfmers and Surfactants for Direct and Inverse Miniemulsion

Wald

Simon

Dietz

et al. 2017

Macromolecular Bioscience

View full text Add to dashboard Cite

show abstract

“…Ethoxyethyl glycidyl ether (EEGE) was synthesized from 2,3-epoxypropan-1-ol (glycidol) and ethyl vinyl ether according to Fitton et al [35], purified by distillation, and stored under a nitrogen atmosphere over a molecular sieve (3 Å).…”

Section: Methodsmentioning

confidence: 99%

Homoserine Lactone as a Structural Key Element for the Synthesis of Multifunctional Polymers

et al. 2017

View full text Add to dashboard Cite

Abstract:The use of bio-based building blocks for polymer synthesis represents a milestone on the way to "green" materials. In this work, two synthetic strategies for the preparation of multifunctional polymers are presented in which the key element is the functionality of homoserine lactone. First, the synthesis of a bis cyclic coupler based on a thiolactone and homoserine lactone is displayed. This coupler was evaluated regarding its regioselectivity upon reaction with amines and used in the preparation of multifunctional polymeric building blocks by reaction with diamines. Furthermore, a linear polyglycidol was functionalized with homoserine lactone. The resulting polyethers with lactone groups in the side chain were converted to cationic polymers by reaction with 3-(dimethylamino)-1-propylamine followed by quaternization with methyl iodide.

show abstract

“…EEGE was prepared according to literature, [34] and the reaction route is illustrated as follows in Figure 1. The Figure 1.…”

Section: Synthesis Of Eegementioning

confidence: 99%

Synthesis and characterization of a novel amphiphilic poly (ethylene glycol)–poly (ε-caprolactone) graft copolymers

Zhang

Tong

Wu³

et al. 2016

Designed Monomers and Polymers

View full text Add to dashboard Cite

A series of amphiphilic graft copolymers PEO-g-PCL with different poly (ε-caprolactone) (PCL) molecular weight were successfully synthesized by a combination of anionic ring-opening polymerization (AROP) and coordination-insertion ring-opening polymerization. The linear PEO was produced by AROP of ethylene oxide (EO) and ethoxyethyl glycidyl ether initiated by 2-(2-methoxyethoxy) ethoxide potassium, and the hydroxyl groups on the backbone were deprotected after hydrolysis. The ring-opening polymerization of CL was initiated using the linear poly (ethylene oxide) (PEO) with hydroxyl group on repeated monomer as macroinitiator and Sn(Oct) 2 as catalyst, then amphiphilic graft copolymers PEO-g-PCL were obtained. By changing the ratio of monomer and macroinitiator, a series of PEO-g-PCL with well-defined structure, molecular weight control, and narrow molecular weight distribution were prepared. The expected intermediates and final products were confirmed by 1 H NMR and GPC analyzes. In addition, these amphiphilic graft copolymers could form spherical aggregates in aqueous solution by self-assemble, which were characterized by transmission electron microscopy, and the critical micelle concentration values of graft copolymers PEO-g-PCL were also examined in this article.

show abstract

Synthesis of Simple Oxetanes Carrying Reactive 2-Substituents

Cited by 222 publications

References 0 publications

Polyglycerol Surfmers and Surfactants for Direct and Inverse Miniemulsion

Polyglycerol Surfmers and Surfactants for Direct and Inverse Miniemulsion

Homoserine Lactone as a Structural Key Element for the Synthesis of Multifunctional Polymers

Synthesis and characterization of a novel amphiphilic poly (ethylene glycol)–poly (ε-caprolactone) graft copolymers

Contact Info

Product

Resources

About