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

✍ Scribed by Wen-Jing Zhou; Sarita S. Naik; Mark J. Kurth; You-Lo Hsieh; John M. Krochta

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 157 KB
• Volume: 36
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(19981130)36:16<2971::aid-pola15>3.0.co;2-p

✦ Synopsis

D-Lactose-O-(vinylbenzyl)oxime (LVO), prepared from ␣-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 2,2Ј-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 1 H-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 ϫ 10 4 to 6.53 ϫ 10 7 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.