Cyclodextrins in Polymer Synthesis:  Free Radical Polymerization of a <i>N</i>-Methacryloyl-11-aminoundecanoic Acid/β-Cyclodextrin Pseudorotaxane in an Aqueous Medium

Jeromin, Julia; Ritter, Helmut

doi:10.1021/ma9815197

Cited by 59 publications

(48 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…211,212 These molecules are able to encapsulate hydrophobic molecules or hydrophobic side groups of polymer as guests into their cavities to form host/guest complexes in aqueous solution and in emulsion. 213,214 Recently, Ritter and co-workers 203 developed a new method to make a nearly water-insoluble photoinitiator (2-hydroxy-2-methyl-1-phenylpropan-1-one) water-soluble by complexation with β-cyclodextrin (Scheme 22). A comparative kinetic study of polymerization reactions initiated with both complexed and uncomplexed photoinitiator revealed a higher polymerization rate and better polymerization yield in the presence of the cyclodextrin/photoinitiator complex.…”

Section: Environmental Safety and Health Considerationsmentioning

confidence: 99%

Photoinitiated Polymerization: Advances, Challenges, and Opportunities

2010

View full text Add to dashboard Cite

The use of photoinitiated polymerization is continuously growing in industry as reflected by the large number of applications in not only conventional areas such as coatings, inks, and adhesives but also high-tech domains, optoelectronics, laser imaging, stereolithography, and nanotechnology. In this Perspective, the latest developments in photoinitiating systems for free radical and cationic polymerizations are presented. The potential use of photochemical methods for step-growth polymerization is also highlighted. The goal is, furthermore, to show approaches to overcome problems associated with the efficiency, wavelength flexibility, and environmental and safety issues in all photoinitiating systems for different modes of activation. Much progress has been made in the past 10 years in the preparation of complex and nanostructured macromolecules by using photoinitiated polymerizations. Thus, the new and emerging applications of photoinitiated polymerizations in the field of biomaterials, surface modification, preparation of block and graft copolymers, and nanocomposites have been addressed.

show abstract

Section: Environmental Safety and Health Considerationsmentioning

confidence: 99%

Photoinitiated Polymerization: Advances, Challenges, and Opportunities

2010

View full text Add to dashboard Cite

show abstract

“…Furthermore, the preparation and polymerization of equimolar cyclodextrin complexes of commercial standard monomers like styrene 1 and methyl methacrylate (MMA have been described. It was also shown that the precipitation polymerization of a cyclodextrin complex of a poorly water-soluble monomer like MMA can be described by kinetic equations similar to those for the classical polymerization in solution [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Cyclodextrin in polymer chemistry: Kinetic studies on the free-radical polymerization of cyclodextrin-complexed styrene from homogeneous aqueous solution

2005

Self Cite

View full text Add to dashboard Cite

Styrene was encapsulated by an equimolar amount of randomly methylated β-cyclodextrin (CD) in water resulting in a water-soluble CD complex. Polymerization of this complex was carried out at 50°C using different amounts of the water-soluble azo-initiator 2,2'-azobis[N,N'-dimethyleneisobutyramidine] dihydrochloride. Unthreading of CD during polymerization led to water-insoluble polystyrene. Analysis of the polymers obtained showed that the polymerization from homogenous aqueous solution can be described by an equation similar to the classical polymerization in solution (number-average degree of polymerization vs. initiator concentration: P n -1 ~ [I] 0.5 ).

show abstract

“…The formation of MPMA/HPCD inclusion complex was further verified by 13 C-NMR spectra [ Fig. 2(B)], for which the detailed data are listed in Table II.…”

Section: Formation and Characterization Of Mpma/hpcd Inclusion Complexmentioning

confidence: 94%

“…23 The yield of the monomer in Scheme 1 was 72%. The 1 H-NMR and 13 C-NMR spectra of the monomer were recorded, as shown in Figure 1. The attributions are also presented in the figure, demonstrating the exact structure and high purity of the monomer.…”

Section: Synthesis and Characterization Of Mpmamentioning

confidence: 99%

“…10,11 In particular, CDs are widely used in polymer chemistry by many researchers. Ritter and coworkers [12][13][14] have prepared a series of methacrylate monomer/methylated-b-cyclodextrin inclusion complexes and polymerized them in aqueous solution. Rimmer and Tattersall 15 have examined the emulsion polymerization of dodecyl and octadecyl methacrylate using a conventional water-soluble initiator and sulphonate surfactant in the presence of CD.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Using hydroxypropyl‐β‐cyclodextrin for the preparation of hydrophobic poly(ketoethyl methacrylate) in aqueous medium

Ding¹,

He²,

Deng³

2009

J of Applied Polymer Sci

View full text Add to dashboard Cite

This work was committed to the polymerization of hydrophobic ketoethyl methacrylate monomer in aqueous medium in the presence of cyclodextrin, instead of polymerizing the monomer in toxic and volatile organic solvents. For this purpose, a new ketoethyl methacrylate monomer, p-methylphenacylmethacrylate (MPMA), was synthesized from the reaction of p-methylphenacylbromide with sodium methacrylate in the presence of triethylbenzylammonium chloride. The monomer was identified with FTIR, 1 H and 13 C-NMR spectroscopies. Hydroxypropyl-bcyclodextrin (HPCD) was used to form a water-soluble host/guest inclusion complex (MPMA/HPCD) with the hydrophobic monomer. The complex was identified with FTIR and NMR techniques and polymerized in aqueous medium using potassium persulfate as initiator. During polymerization the resulting hydrophobic methacrylate polymer precipitated out with a majority of HPCD left in solution and a minority of HPCD bonded on the resulting polymer. The thus-prepared polymer exhibited little difference from the counterparts obtained in organic solvent in number average molecular weight (M n ), polydispersity (M w /M n ) and yield. The investigation provides a novel strategy for preparing hydrophobic ketoethyl methacrylate polymer in aqueous medium by using a monomer/HPCD inclusion complex.

show abstract

Cyclodextrins in Polymer Synthesis: Free Radical Polymerization of a N-Methacryloyl-11-aminoundecanoic Acid/β-Cyclodextrin Pseudorotaxane in an Aqueous Medium

Cited by 59 publications

References 20 publications

Photoinitiated Polymerization: Advances, Challenges, and Opportunities

Photoinitiated Polymerization: Advances, Challenges, and Opportunities

Cyclodextrin in polymer chemistry: Kinetic studies on the free-radical polymerization of cyclodextrin-complexed styrene from homogeneous aqueous solution

Using hydroxypropyl‐β‐cyclodextrin for the preparation of hydrophobic poly(ketoethyl methacrylate) in aqueous medium

Contact Info

Product

Resources

About