Dimerizations of acrylate monomers with sodium hydroxymethanesulfinate and characterization of the products

Cheng‐Chien ‐C Wang, Jen‐Feng ‐F Kuo, Chuh-Yung Chen

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The reactions of sodium hydroxymethanesulfinate (sodium formaldehyde sulfoxylate, SFS) with various monomers, including acrylates, methacrylates, styrene and vinyl acetate, were studied. The reaction products formed depended on the molecular structure of the monomers and acidity of the reaction solution. Among the monomers studied, acrylates with resonance stability values Q between 0,38 and 0,45 produced diacrylate sulfones in neutral conditions. The other monomers or reaction conditions did not result in a dimer. The obtained diacrylate sulfones were characterized by elemental analysis, mass spectrometry, IR spectra, normal 1H and 13C NMR, CHn (n = 1, 2 and 3) subspectra by Distortionless Enchancement by Polarization Transfer at θ = 3π/4, as well as by 1H‐ 13C 2D‐NMR spectra using Correlated Spectroscopy and Heteronuclear Multiple Bonding Correlation methods. A possible reaction mechanism for the formation of dimers is suggested. The morphology and thermal properties of these diacrylate sulfones were determined.

Original languageEnglish
Pages (from-to)1493-1502
Number of pages10
JournalMacromolecular Chemistry and Physics
Volume195
Issue number5
DOIs
Publication statusPublished - 1994 Jan 1

Fingerprint

Dimerization
acrylates
dimerization
Sulfones
sulfones
monomers
Monomers
Acrylates
Sodium
sodium
products
Dimers
dimers
Styrene
Methacrylates
Correlation methods
formaldehyde
Reaction products
Formaldehyde
styrenes

All Science Journal Classification (ASJC) codes

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry
  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

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title = "Dimerizations of acrylate monomers with sodium hydroxymethanesulfinate and characterization of the products",
abstract = "The reactions of sodium hydroxymethanesulfinate (sodium formaldehyde sulfoxylate, SFS) with various monomers, including acrylates, methacrylates, styrene and vinyl acetate, were studied. The reaction products formed depended on the molecular structure of the monomers and acidity of the reaction solution. Among the monomers studied, acrylates with resonance stability values Q between 0,38 and 0,45 produced diacrylate sulfones in neutral conditions. The other monomers or reaction conditions did not result in a dimer. The obtained diacrylate sulfones were characterized by elemental analysis, mass spectrometry, IR spectra, normal 1H and 13C NMR, CHn (n = 1, 2 and 3) subspectra by Distortionless Enchancement by Polarization Transfer at θ = 3π/4, as well as by 1H‐ 13C 2D‐NMR spectra using Correlated Spectroscopy and Heteronuclear Multiple Bonding Correlation methods. A possible reaction mechanism for the formation of dimers is suggested. The morphology and thermal properties of these diacrylate sulfones were determined.",
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Dimerizations of acrylate monomers with sodium hydroxymethanesulfinate and characterization of the products. / Wang, Cheng‐Chien ‐C; Kuo, Jen‐Feng ‐F; Chen, Chuh-Yung.

In: Macromolecular Chemistry and Physics, Vol. 195, No. 5, 01.01.1994, p. 1493-1502.

Research output: Contribution to journalArticle

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