Solvent effects in radical copolymerization III. Methacrylamide

Saini, G.; Leoni, Alvaro; Franco, Simone

doi:10.1002/macp.1971.021470118

Cited by 46 publications

(8 citation statements)

References 3 publications

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“…In the radical copolymerization of 3 with acrylamide, the molar fraction of the glyco‐unit in the resulting copolymer was higher than that in feed. However, in the corresponding copolymerization with styrene, it was comparable to that in the feed, as expected from the monomer reactivity of styrene and methacryloyl derivative 19…”

Section: Resultssupporting

confidence: 63%

“…For example, the molar fraction of the glyco‐unit in the copolymer obtained in the copolymerization with a 0.20 molar fraction of 4 in the feed was estimated to be only 0.08. The estimated value (0.08) is much lower than that (0.15) expected from the monomer reactivity in the copolymerization of methacrylamide with styrene ( r 1 = 0.48 and r 2 = 1.4) 19. The copolymer was soluble not only in Me 2 SO but also in benzene and tetrahydrofuran, like homopolystyrene.…”

Section: Resultsmentioning

confidence: 67%

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Synthesis and polymerization of new styryl and methacryloyl monomers containing acidic saccharide moieties

Shimura¹,

Hashimoto²,

Yamanaka³

et al. 2001

J. Polym. Sci. A Polym. Chem.

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New styryl-type water-insoluble and methacryloyl-type water-soluble monomers, N-(p-vinylbenzyl)-1,2-O-isopropylidene-6-D-glucofuranuronamide and N-(2methacryloylamino)ethyl-1,2-O-isopropylidene-6-D-glucofuranuronamide, were synthesized from the most common acidic saccharide, D-glucuronic acid. Their radical homopolymerizations and copolymerizations with styrene and acrylamide were tried under various conditions. The isopropylidene groups in the resulting polymers were removed in a mixture of trifluoroacetic acid and water (2/1 v/v) to give the corresponding polymers with many pendant D-glucopyranuronyl groups with reactive reducing groups. The pendant reducing ends may be useful as potential binding sites under a hydrophilic atmosphere.

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Section: Resultssupporting

confidence: 63%

Section: Resultsmentioning

confidence: 67%

Synthesis and polymerization of new styryl and methacryloyl monomers containing acidic saccharide moieties

Shimura¹,

Hashimoto²,

Yamanaka³

et al. 2001

J. Polym. Sci. A Polym. Chem.

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“…It has been reported that solvents influence strongly the radical copolymerizations of acrylamide, 1 -8 methacrylamide 9 and their Nmonosubstituted derivatives, 10 • 11 though the copolymerization behavior of N,N-dimethylacrylamide (DMA) 12 is not affected by the solvent employed. The solvent effect on the copolymerizations has been discussed in terms of the influence of the solvent properties, i.e., polarity, dielectric constant, hydrogenbonding ability, etc., on the monomer association, 3 -6 keto-enol equilibrium, 12 and conjugation between C=C and C=O double bonds.…”

mentioning

confidence: 99%

Solvent Effect on the Radical Copolymerization of N-Methyl- and N,N-Dimethylacrylamides and N-Methylmethacrylamide with Methyl Methacrylate

Kodaira

Yang

Aida

1988

Polym J

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ABSTRACT:Solvent effect on radical copolymerizations of N-methylacrylamide (AA) and Nmethylmethacrylamide (MA) with methyl methacrylate (MMA, M2) was studied using benzene (BZ), dioxane (DO), acetonitrile (ACN), ethanol (EtOH), and N,N-dimethylformamide (DMF). Spectroscopic studies revealed that the solvents influence these amide monomers (M1) with regards to their association by hydrogen-bonding and dipole-dipole interaction. The solvent ability which makes the self-associations of AA and MA more effective decreases in the order of BZ >DO> ACN > EtOH > DMF. The higher the solvent ability for the self-associations of the amide monomers, the larger the values of r1. The extent of the solvent effect on both the monomers decreased with decreasing order of their self-association tendencies, i.e., AA> MA. M 1 concentration around M 1 • radical is considered to be enhanced by its association with M 1 in the solvent with higher ability for the self-association of M1. This enhances the propagation-rate between M 1 • radical and M 1 and increases apparently k11 as compared with k 12 . The r 2 values did not change depending on solvents except the copolymerization in BZ. The interactions between MMA and the amide monomers are too weak to raise their local concentrations around M2 • radical. BZ iii.creases extraordinarily r1 and decreases r2 , respectively. Copolymers precipitated during copolymerization in BZ are considered to adsorb the amide monomers, since their interactions with BZ are extremely weak. This increases the local M1 concentration around both M1 • and M2 • radicals. BZ influences even the copolymerization of N,N-dimethylacrylamide which has been considered to be independent of the solvents. Dipole-dipole interaction has been ascribed to this solvent effect.KEY WORDS Solvent Effect / Radical Copolymerization / NMR / IR /

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“…This definitely proves the formation of dye‐aggregates as expected from the reactivity ratio of 1.3 discussed above. It should be mentioned that many examples of similar copolymerization parameters of both r A > 1and r B > 1 are known from literature, for example, acrylamide and styrene ( r 1 = 1.38, r 2 = 1.27 in dioxane)27 and methacrylamide and styrene ( r 1 = 1.29, r 2 = 1.46 in dioxane) 28…”

Section: Resultsmentioning

confidence: 99%

Color Indicator for Supramolecular Polymer Chemistry: Phenolphthalein‐Containing Thermo‐ and pH‐Sensitive N‐(Isopropyl)acrylamide Copolymers and β‐Cyclodextrin Complexation

Fleischmann¹,

Ritter²

2013

Macromol. Rapid Commun.

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The copolymerization parameters of N-(isopropyl)acrylamide (1) and N-(2-hydroxy-5-(1-(4-hydroxyphenyl)-3-oxo-1,3-dihydroisobenzofuran-1-yl)benzyl)acrylamide (2) are determined. For both monomers, the homoaddition proceeds slightly faster than the heteroaddition step; however, the polymer formation occurs in a statistic fashion. Copolymers of different compositions are prepared and the cloud points are determined. Thereby, a significant influence of the concentration of monomer 2 and the pH value is found. For the first time, the complexation of polymer attached phenolphthalein by β-cyclodextrins is shown. Furthermore, it is possible to achieve a decomplexation by the addition of suitable guest molecules. Both procedures can be followed with the naked eye.

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Solvent effects in radical copolymerization III. Methacrylamide

Cited by 46 publications

References 3 publications

Synthesis and polymerization of new styryl and methacryloyl monomers containing acidic saccharide moieties

Synthesis and polymerization of new styryl and methacryloyl monomers containing acidic saccharide moieties

Solvent Effect on the Radical Copolymerization of N-Methyl- and N,N-Dimethylacrylamides and N-Methylmethacrylamide with Methyl Methacrylate

Color Indicator for Supramolecular Polymer Chemistry: Phenolphthalein‐Containing Thermo‐ and pH‐Sensitive N‐(Isopropyl)acrylamide Copolymers and β‐Cyclodextrin Complexation

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