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. 2012:8:2176-83.
doi: 10.3762/bjoc.8.245. Epub 2012 Dec 13.

Influence of cyclodextrin on the solubility and the polymerization of (meth)acrylated Triton(®) X-100

Melanie Kemnitz  1 , Helmut Ritter
Affiliations

Influence of cyclodextrin on the solubility and the polymerization of (meth)acrylated Triton(®) X-100

Melanie Kemnitz et al. Beilstein J Org Chem. 2012.

Abstract

Triton(®) X-100 (poly(ethylene glycol) tert-octylphenyl ether) was (meth)acrylated and polymerized in the absence and presence of randomly methylated β-cyclodextrin (RAMEB-CD). Triton(®)-polymers that were polymerized with RAMEB-CD in water were compared with polymers that were synthesized in organic solvents after the addition of RAMEB-CD. The polymers were characterized by (1)H NMR and FTIR spectroscopy, matrix-assisted laser desorption ionization mass spectrometry (MALDI-TOF MS), dynamic light scattering (DLS), gel-permeation chromatography (GPC) and turbidity measurements. Additionally, the viscosity change of the methacrylic homopolymer with RAMEB-CD was evaluated.

Keywords: (meth)acrylated Triton®; Triton® X-100 (poly(ethylene glycol)tert-octylphenyl ether); randomly methylated β-cyclodextrin (RAMEB-CD); rheology.

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Figures

Figure 1
Figure 1
Chemical structure of Triton® X-100 (1).
Figure 2
Figure 2
Solubility in water of 0.2 wt % Triton® X-100 (1) and its different assumed complexes with RAMEB-CD (1a and 1b) according to the transparence measurement.
Scheme 1
Scheme 1
Idealized reaction of the complexation of the (meth)acrylic monomer derived from Triton® (2 and 3) with one and 2 equiv of RAMEB-CD.
Scheme 2
Scheme 2
Homopolymerization of the uncomplexed monomers 2 and 3 to the polymers 8 and 9 in DMF with AIBN as initiator.
Scheme 3
Scheme 3
Polymerization of the RAMEB-CD complexed monomers 4, 5, 6 and 7 to the homopolymers 10, 11, 12 and 13 in water with VA-044 as initiator.
Figure 3
Figure 3
Transmittance [%] and zero-shear-viscosity [Pas] as a function of temperature for a 50 wt % solution of polymer 8. (I → II: Viscosity decreases with higher temperature; II → III: Gradual decomplexation of the polymer, RAMEB-CD molecules slip off from the polymer side chain, aggregates are formed; III: Precipitation of the polymer).
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