Hydroxyethylmethacrylate and

Kragl and Dreisbach reported on the asymmetric diethylzinc addition to benzaldehyde using a chiral homogeneous catalyst supported on a soluble polymethacrylate.[55] l, L-Diphenyl-L-prolinol was bound to a copolymer from 2-hydroxyethylmethacrylate and octadecylmethacrylate forming a soluble catalyst with a Mw of 96 000 (Figure 4.39). 

Other functionalized supports that are able to serve in the asymmetric dihydroxylation of alkenes were reported by the groups of Sharpless (catalyst 25) [88], Sal-vadori (catalyst 26) [89-91] and Cmdden (catalyst 27) (Scheme 4.13) [92]. Commonly, the oxidations were carried out using K3Fe(CN)g as secondary oxidant in acetone/water or tert-butyl alcohol/water as solvents. For reasons of comparison, the dihydroxylation of trons-stilbene is depicted in Scheme 4.13. The polymeric catalysts could be reused but had to be regenerated after each experiment by treatment with small amounts of osmium tetroxide. A systematic study on the role of the polymeric support and the influence of the alkoxy or aryloxy group in the C-9 position of the immobilized cinchona alkaloids was conducted by Salvadori and coworkers [89-91]. Co-polymerization of a dihydroquinidine phthalazine derivative with hydroxyethylmethacrylate and ethylene glycol dimethacrylate afforded a functionalized polymer (26) with better swelling properties in polar solvents and hence improved performance in the dihydroxylation process [90]. 

In an effort to develop a peroral application system for insulin, Saffran was the first to use azopolymers as protective colon delivery coating, by use of the aforementioned strategy of azo-linked prodrugs [58, 59], Originally, he used azo-linked copolymers of styrene and hydroxyethylmethacrylate to coat and protect the insulin. However, this approach is not restricted to hydroxyethylmethacrylate and can indeed be accomplished in the same way by an almost unlimited number of similar polymer types. 

Yu. N. Bolbukh, Ye. P. Mamunya, and V. A. Tertykh, Thermomechanical investigation of composites based on 2-hydroxyethylmethacrylate and high disperse initial and modified silicas, J. Therm. Anal. Cal. 81(1), 15-20 (2005). 

Not only polystyrene supports, also other polymer supports were used in the preparation of polymeric amino alcohol ligands for dialkylzinc alkylation. For example, a vinylferrocene derivative with A,N -disubstituted norephedrine was copolymerized with vinylferrocene [60]. This polymeric chiral ligand (53) was used in the ethylation of aldehydes with moderate activity. Brown has reported that chiral oxazaborolidines have catalytic activity in the addition of diethyl zinc to aldehydes [61]. Polymers bearing chiral oxazaborolidines 37 were also active in the reaction and result on moderate enantioselectivity (<58 % ee) [62]. Enantiopure a,a -diphenyl-L-prolinol coupled to a copolymer prepared from 2-hydroxyethylmethacrylate and octadecyl methacrylate... 

A particularly large number of applications of cyclophosphazene derivatives has been noted. Of particular interest is the large number of reports focusing on methacryloyloxyethoxy derivatives, typically N3Pj(0CH2CH20C(0)C(Me)=CH2) j. Uses claimed for derivatives center on the easy cure which can be accomplished due to the reactivity of the appended methacrylate. Several reports focus solely on the preparation of the hexasubstituted derivative either from 2-hydroxyethylmethacrylate and (NPCl2)3 or by two step indirect routes which have been... 

Quantitative photophysical, photochemical and photopolymerisation data are presented on five novel water soluble benzophenone photoinitiators. Phosphorescence quantum yields, triplet lifetimes and transient formation on conventional flash photolysis correlate with the ability of the initiators to photoinduce the polymerisation of 2-hydroxyethylmethacrylate and a commercial monoacrylate resin in aqueous media. The results indicate that the lowest excited triplet state of the initiator is abstracting an electron from the tertiary amine cosynergist probably via a triplet exciplex followed by hydrogen atom abstraction. This is confirmed by a detailed analysis on the effect of oxygen, pH and the ionisation potential of the amine on transient formation and photopolymerisation. Using photocalorimetry a linear correlation is found between the photopolymerisation quantum yields of the initiators and their photoreduction quantum yields in aqueous media. 

Wandrey and co-workers pioneered the use of homogeneous catalysts bound to soluble supports in continuously operating membrane reactors (CFMRs). In 1996 Kragl and Dreisbach reported on a chiral polymer-enlarged homogeneous catalyst, which was used for the enantioselective addition of diethylzinc to benzaldehyde [Eq. (3)] [9]. The catalyst consisted of a soluble polymeric support, a copolymer of 2-hydroxyethylmethacrylate and octadecyl methacrylate, combined with a,a-diphe-nyl-L-prolinol as the active organocatalytic site (2). 

Imprinted polymers are frequently prepared by radical copolymerization of two of the most used cross-linkers ethylene dimethacrylate (EDMA) and trimethyl-olpropane trimethacrylate (TRIM) with one of the many functional monomers reported in literature (mainly methacrylic acid, acrylamide, 4-vinylpyridine, or tri-fluoromethacrylic acid, but also 2-hydroxyethylmethacrylate and A,A-diethyl-aminoethylmethacrylate (see this book. Chapter 7) The polymers obtained as bulk monoliths or dispersed microparticles have properties that are very suitable for liquid chromatographic applications. 

A BMI formulation, a mixture of 4,4 -diaminodiphenyImethane-based BMI ( 50%), stjrrene, 2-hydroxyethylmethacrylate and a curing agent (trigonox HM)... 

Rossner M, Rossner F, Bachmann F, Wiest L, Rzany B. Risk of severe adverse reactions to an injectable filler based on a fixed combination of hydroxyethylmethacrylate and ethyl-methacrylate with hyaluronic acid. Dermatol Surg 2009 25(1) 367-74. 

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