Syntheses of new amino‐functionalized methacrylates and their use in free radical polymerizations
John M. GeurtsChristianne GöttgensMarco A. I. Van GraefschepeRob W. A. WellandJ. J. G. Steven van EsAnton L. German
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Abstract For use in emulsion and solution copolymerization a series of novel amino‐functional methacrylates has been synthesized, most of which have seldom, or never, been described in the literature before. In this investigation, the preparation of the hydrochloric and/or tosylate salt of the monomers aminoethyl, 3‐amino‐1‐propyl, 5‐amino‐1‐pentyl, 6‐amino‐1‐hexyl and 11‐amino‐1‐undecyl methacrylate will be described, along with the characterization of the parameters water solubility, pK a and chemical stability. The homopolymers of these monomers have been prepared and characterized. Results show the occurrence of an acyl migration upon neutralization of the monomers aminoethyl‐ and 3‐amino‐1‐propyl methacrylate. This migration does not occur in the monomer 5‐amino‐1‐pentyl methacrylate, which makes it possible to synthesize the neutralized monomer although, after neutralization, a Michael addition occurs, resulting in a limited lifetime. Copolymerizations have been performed in emulsion. The monomer aminopentyl methacrylate especially proved to be suitable for emulsion copolymerizations when used under controlled conditions. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 80: 1401–1415, 2001Cite
Abstract The copolymerization of monomethyl maleate (MMM) or monomethyl fumarate (MMF) with styrene is investigated. The dependence of the copolymerization rates on the composition of the monomer mixture and the monomer reactivity ratios r are determined. An identical structure of the MMM and MMF polymer radicals was found, that is the k 21 ‐values of both copolymerization systems are equal (monomer 1 ≡ styrene; monomer 2 ≡ MMM or MMF). From this knowledge the difference of the copolymerization rates between MMM and MMF can be attributed to the k 12 ‐values.
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Abstract For use in emulsion and solution copolymerization a series of novel amino‐functional methacrylates has been synthesized, most of which have seldom, or never, been described in the literature before. In this investigation, the preparation of the hydrochloric and/or tosylate salt of the monomers aminoethyl, 3‐amino‐1‐propyl, 5‐amino‐1‐pentyl, 6‐amino‐1‐hexyl and 11‐amino‐1‐undecyl methacrylate will be described, along with the characterization of the parameters water solubility, pK a and chemical stability. The homopolymers of these monomers have been prepared and characterized. Results show the occurrence of an acyl migration upon neutralization of the monomers aminoethyl‐ and 3‐amino‐1‐propyl methacrylate. This migration does not occur in the monomer 5‐amino‐1‐pentyl methacrylate, which makes it possible to synthesize the neutralized monomer although, after neutralization, a Michael addition occurs, resulting in a limited lifetime. Copolymerizations have been performed in emulsion. The monomer aminopentyl methacrylate especially proved to be suitable for emulsion copolymerizations when used under controlled conditions. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 80: 1401–1415, 2001
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Abstract The method for evaluating the Damkohler number for monomer transport during emulsion homopolymerization is extended to copolymerization. It is shown that monomers that are not monomer‐transport limited during homopolymerization may become more so during binary copolymerization, and monomers that are monomer‐transport limited during homopolymerization may become less so during binary copolymerization.
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Films Based on New Methacrylate Monomers: Synthesis, Characterisation and Electro-Optical Properties
Abstract A number of liquid crystal monomers based on methacrylate derivatives were synthesised by novel mild and solventless procedures under microwave irradiation. Their photo- and thermo assisted homo- and co-polymerizations with glycidyl methacrylate were investigated. The resulting polymers were characterised by NMR, GPC, DSC, and SEM to determine their structures and properties. The effects of the structures of the monomers on the electro-optical properties were correlated. Keywords: Electro-optical propertiesgreen chemistry synthesisliquid crystal polymerPDLC Acknowledgment This work was supported by Fundaçãopara a Ciência e Tecnologia through the project PTDC/CTM/69145/2006.
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The development of fluoroolefin copolymer resins,and the relative researches on the copolymerization between fluoroalkenes and dry proton monomers are summarized.In most cases,random copolymers are obtained during the copolymerization of fluorinated alkenes.The types of fluorinated monomer and co-monomer are very much involved in polymerization reaction,however,finished products can mainly be divided into thermoplastic,elastomer,and thermoelatomer according to their performance and application.Some properties of fluoropolymer,such as solubility,cross-linking curability,adhesion,etc.,can be compensated by introducing some monomers with special function to the copolymerization system.In addition,the Q-e parameters of some fluorinated monomers are listed in this article.Finally,alternating copolymerization based on electron-withdrawing fluorinated monomer with electro-donating hydrogenated monomer is presented and illustrated with examples.
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Abstract Free radical-initiated copolymerization of 2-vinylnaphthalene (2-VNA) with benzylidenemalononitrile (BzMN) was performed in toluene to low conversion and to high conversion in a Calvet microcalorimeter. Under different monomer-to-monomer ratios in the feed at low and high conversion copolymerization, it was found that the usual terminal scheme of copolymerization fitted and that there was no significant kinetic effect of the penultimate unit. The reactivity ratios in low conversion copolymerizations were r1 = 0.85 and r2 = 0. In all cases, regardless to the monomer-to-monomer ratios in the feed, an excess of 2-VNA was present in copolymers. T g values of copolymers are between 186 and 220 °C, and they decrease with the increase of 2-VNA sequences in copolymer chains. Poly(2-VNA-co-BzMN) are film-forming materials which decompose by a one-step mechanism. Depending on the comonomers content in the copolymer, the weight loss is 50% between 325 and 360 °C, and 90% at 400 °C.
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