Novel poly(ɛ-caprolactone)s bearing amino groups: Synthesis, characterization and biotinylation

A novel functional ɛ-caprolactone monomer containing protected amino groups, γ-(carbamic acid benzyl ester)-ɛ-caprolactone (γCABɛCL), was successfully synthesized. A series of copolymers [poly(CL-co-CABCL)] were prepared by ring-opening polymerization of ɛ-caprolactone (CL) and γCABɛCL in bulk using...

Full description

Saved in:
Bibliographic Details
Published in:Reactive & functional polymers 2010-07, Vol.70 (7), p.400-407
Main Authors: Yan, Jinliang, Zhang, Yi, Xiao, Yan, Zhang, Yan, Lang, Meidong
Format: Article
Language:English
Subjects:
Amino groups
Applied sciences
Baeyer–Villiger reaction
Bearing
Biotinylation
Copolymerization
Copolymers
Differential scanning calorimetry
Exact sciences and technology
Hydrogenolysis
Monomers
Nuclear magnetic resonance
Organic polymers
Palladium
Physicochemistry of polymers
Poly(ɛ-caprolactone)
Preparation, kinetics, thermodynamics, mechanism and catalysts
Ring-opening polymerization
Synthesis
γ-(Carbamic acid benzyl ester)-ɛ-caprolactone
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A novel functional ɛ-caprolactone monomer containing protected amino groups, γ-(carbamic acid benzyl ester)-ɛ-caprolactone (γCABɛCL), was successfully synthesized. A series of copolymers [poly(CL-co-CABCL)] were prepared by ring-opening polymerization of ɛ-caprolactone (CL) and γCABɛCL in bulk using tin (II)-2-ethylhexanoate [Sn(Oct)2] as catalyst. The morphology of the copolymers changed from semi-crystalline to amorphous with increasing γCABɛCL monomer content. They were further converted into deprotected copolymers [poly(CL-co-ACL)] with free amino groups by hydrogenolysis in the presence of Pd/C. After deprotection, the free amino groups on the copolymer were further modified with biotin. The monomer and the corresponding copolymers were characterized by 1H NMR, 13C NMR, FT-IR, mass, GPC and DSC analysis. The obtained data have confirmed the desired monomer and copolymer structures.
ISSN:1381-5148
DOI:10.1016/j.reactfunctpolym.2010.03.008