Cyclodextrin in polymer synthesis: a green way to polymers

Ritter, Helmut; Tabatabai, Monir

doi:10.1016/s0079-6700(02)00022-9

Cited by 90 publications

(54 citation statements)

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“…1,16,17 In literature, the inclusion complex of ketoethyl methacrylate monomer and HPCD has not yet been found up to now.…”

Section: Formation and Characterization Of Mpma/hpcd Inclusion Complexmentioning

confidence: 99%

“…Cyclodextrins (CDs), as cyclic oligosaccharides consisting of 6 (a), 7 (b), or 8 (c) glucopyranose units linked by 1,4-a-glucosidic bonds, [1][2][3] are well-known to form inclusion complexes with suitable organic molecule guests due to CDs' polar hydrophilic outer shell and relatively hydrophobic cavity. [4][5][6][7][8] The occurrence of inclusion complex leads to a drastic change in the solubilities and reactivities of guest molecules.…”

Section: Introductionmentioning

confidence: 99%

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

Ding¹,

He²,

Deng³

2009

J of Applied Polymer Sci

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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.

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“…1,16,17 In literature, the inclusion complex of ketoethyl methacrylate monomer and HPCD has not yet been found up to now.…”

Section: Formation and Characterization Of Mpma/hpcd Inclusion Complexmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Ding¹,

He²,

Deng³

2009

J of Applied Polymer Sci

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“…Our group, for these reasons is focused on the use of cyclodextrin (CD) in polymer chemistry. Meanwhile CD's have received a great deal of industrial attention [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29].…”

Section: Introductionmentioning

confidence: 99%

Novel Polymerization of Myrcene in Aqueous Media via Cyclodextrin-Complexes

Choi

Ritter

2007

E-Polymers

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Free radical homopolymerization with methylated β-cyclodextrin (CD) complexed myrcene (1a) and co-polymerization of 1a with diethyl fumarate (2a) and styrene (3a) were carried out using redox initiator in aqueous media at room temperature. Control experiments showed that uncomplexed myrcene (1) does not polymerize under similar conditions in water. The polymers obtained were characterized by means of 1 H/ 13 C-NMR spectroscopy, differential scanning calorimetry (DSC) and gel-permeation chromatography (GPC). Additionally, Nisopropylacrylamide containing copolymer was synthesized in water using redox initiator and the lower critical solution temperature (LCST) behaviour was studied.

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“…[56][57][58][59][60] Cyclodextrins have been utilized in polymer synthesis. 61 The strategies to prepare hyperbranched polysaccharides, 62,63 the synthesis of glycopolymers by post-polymerizations, 64 and the surface initiated polymerizations of the monomers featuring saccharides 16,65 have been developed. Attention has focused on glycoconjugated polymers that include sulfated saccharide-based polymers for glycosaminoglycan mimetic biomaterials, 35 glycopolymer-polypeptide hybrids for glycopeptides mimics, 37 glycoconjugated polymeric nanoparticles with therapeutic interest, 66,67 glycopolymer nanofibrous sticks for protein separations, 68 thermoresponsive glycopolymers for the control of bacterial aggregation, 15 cationic glycopolymers for DNA delivery, 69 saccharide imprinting gels for artificial antibodies, 70,71 and saccharide arrays on the backbone of -conjugation polymers for biosensors.…”

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confidence: 99%

Synthesis of Glycoconjugated Branched Macromolecular Architectures

Narumi

Kakuchi

2008

Polym J

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The applications developed by polymer chemistry using saccharides have significantly expanded, thus it is required that continuous efforts be made to develop routes for preparing glycoconjugated polymers as well as utilizing sugar resources for the polymer synthesis. We now provide an overview focusing on the preparations of the vinyl polymers with threedimensional structures utilizing functionality of saccharides and the syntheses of glycoconjugated branched vinyl polymers. As the first topic, we describe that star-like reversed-type polymeric aggregates have been generated by end-functionalized polymers with saccharides, in which the functionalities of malto-oligosaccharides have been utilized to control the sizes of the hydrophilic and hydrophobic domains of the aggregates. The second section describes the star polymer syntheses with the arm numbers regulated by the functionalities of glucose, inositol, sucrose, and cyclodextrins. In the last half sections, the preparations of a new class of glycoconjugates have been reviewed, which includes glycopolymer stars, hyperbranched glycopolymers, star microgels with a glycoconjugated periphery or core, and poly(vinyl saccharide) microgels.KEY WORDS: Glycoconjugate / Glycopolymer / Star Polymer / Reversed Micelle / Hyperbranched Polymer / Microgel / Saccharides have been recognized as important in polymer chemistry as elements for molecular and cell recognitions, strong and bio-harmless hydrophilic segments, chirality sources, and inexhaustible raw materials independent of oils. Thus, there have been numerous reports on the polymers related to saccharides especially during the past two and a half decades 1-12 as well as in the very recent years, 13-16 asymmetric polymerizations with saccharides generate main-chain chiral polymers, 17,18 and enzymatic polymerizations produce bioresorbable plastics from sugar resources. 19,20 A noteworthy progresses in the research field of glycoconjugated polymers during the past decade include the adaptation of precise polymerizations. Anionic polymerizations, 21 cationic polymerizations, 22 ring-opening metathesis polymerizations (ROMP), 23,24 and anionic ring-opening polymerizations 25 have produced glycopolymers with well-defined structures and block copolymers with the glycopolymer segments. More extensively, controlled radical polymerizations [26][27][28][29][30][31][32][33][34] have been applied as versatile synthetic methods for the well-defined glycopolymer, which include the cyanoxyl-mediated free-radical polymerizations, 35-37 the nitroxide-mediated controlled radical polymerization (NMP), 38-44 the atom transfer radical polymerization (ATRP), [45][46][47][48][49][50] and the reversible addition-fragmentation chain transfer (RAFT) polymerization. [51][52][53][54] For the controlled radical polymerizations, the synthesis of well-defined glycopolymers without protection and deprotection procedures [35][36][37]47,48,[51][52][53][54] and the miniemulsion polymerization of glycomonomers 55 are current topics. A multivalent sacch...

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Cyclodextrin in polymer synthesis: a green way to polymers

Cited by 90 publications

References 0 publications

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

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

Novel Polymerization of Myrcene in Aqueous Media via Cyclodextrin-Complexes

Synthesis of Glycoconjugated Branched Macromolecular Architectures

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