Synthesis and characterization of random hydrophilic/hydrophobic copolymers of styrene and D-lactose-O-vinylbenzylhydroxime

Wen Jing Zhou, Sarita S. Naik, Mark J. Kurth, You Lo Hsieh, John M. Krochta

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

D-Lactose-O-(vinylbenzyl)oxime (LVO), prepared from α-D-lactose and [O-(vinylbenzyl)oxy]amine (1) was copolymerized with styrene (ST) in dimethylsulfoxide (DMSO)-toluene (1 : 1, v/v) at 65°C using 2,2′-azobisisobutyronitrile (AIBN) as a free radical initiator. The polymerization was rapid when using AIBN as the initiator. The resultant copolymers were characterized by elemental analyses, infrared, viscometry, TGA, DSC, and 1H-NMR spectroscopy. The poly(ST-co-LVO) had an intrinsic viscosity in the range of 0.11-0.51 dL/g in DMSO at 30°C. The molecular weight was determined by gel permeation chromatography (GPC), and the molecular weight of the resulting polymers ranged from 2.11 × 104 to 6.53 × 107 with low polydispersities. The solubility of the copolymers with different monomer compositions in solvents of varied polarities was also studied. Incorporation of up to 65% (mol %) of lactose-based monomer onto polystyrene backbone led to a water-soluble polymer. Thermal behavior of the synthesized copolymers was evaluated by thermogravimetric analysis (TGA) and correlated very well with the polymer composition. Introduction of a pendant disaccharide compromised the thermal stability of the copolymer. The synthetic approach described in this report provides a route to prepare a novel disaccharide surfactant polymer with well-defined structures and hydrophilic/hydrophobic balances, by adjusting feed ratio of the lactose-based monomer (1) to styrene.

Original languageEnglish (US)
Pages (from-to)2971-2978
Number of pages8
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume36
Issue number16
StatePublished - Nov 30 1998

Fingerprint

Lactose
Styrene
Polymers
Copolymers
Monomers
Disaccharides
Dimethyl Sulfoxide
Thermogravimetric analysis
Molecular weight
Oximes
Polystyrenes
Viscosity measurement
Toluene
Gel permeation chromatography
Polydispersity
Chemical analysis
Free radicals
Surface-Active Agents
Nuclear magnetic resonance spectroscopy
Free Radicals

Keywords

  • Amphiphilic copolymer
  • Copolymerization
  • Polymeric surfactant
  • Radical polymerization
  • Solubility
  • Solution polymerization
  • Styrene
  • Thermostability

ASJC Scopus subject areas

  • Materials Chemistry
  • Polymers and Plastics

Cite this

Synthesis and characterization of random hydrophilic/hydrophobic copolymers of styrene and D-lactose-O-vinylbenzylhydroxime. / Zhou, Wen Jing; Naik, Sarita S.; Kurth, Mark J.; Hsieh, You Lo; Krochta, John M.

In: Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 36, No. 16, 30.11.1998, p. 2971-2978.

Research output: Contribution to journalArticle

Zhou, Wen Jing ; Naik, Sarita S. ; Kurth, Mark J. ; Hsieh, You Lo ; Krochta, John M. / Synthesis and characterization of random hydrophilic/hydrophobic copolymers of styrene and D-lactose-O-vinylbenzylhydroxime. In: Journal of Polymer Science, Part A: Polymer Chemistry. 1998 ; Vol. 36, No. 16. pp. 2971-2978.
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AB - D-Lactose-O-(vinylbenzyl)oxime (LVO), prepared from α-D-lactose and [O-(vinylbenzyl)oxy]amine (1) was copolymerized with styrene (ST) in dimethylsulfoxide (DMSO)-toluene (1 : 1, v/v) at 65°C using 2,2′-azobisisobutyronitrile (AIBN) as a free radical initiator. The polymerization was rapid when using AIBN as the initiator. The resultant copolymers were characterized by elemental analyses, infrared, viscometry, TGA, DSC, and 1H-NMR spectroscopy. The poly(ST-co-LVO) had an intrinsic viscosity in the range of 0.11-0.51 dL/g in DMSO at 30°C. The molecular weight was determined by gel permeation chromatography (GPC), and the molecular weight of the resulting polymers ranged from 2.11 × 104 to 6.53 × 107 with low polydispersities. The solubility of the copolymers with different monomer compositions in solvents of varied polarities was also studied. Incorporation of up to 65% (mol %) of lactose-based monomer onto polystyrene backbone led to a water-soluble polymer. Thermal behavior of the synthesized copolymers was evaluated by thermogravimetric analysis (TGA) and correlated very well with the polymer composition. Introduction of a pendant disaccharide compromised the thermal stability of the copolymer. The synthetic approach described in this report provides a route to prepare a novel disaccharide surfactant polymer with well-defined structures and hydrophilic/hydrophobic balances, by adjusting feed ratio of the lactose-based monomer (1) to styrene.

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