3‐Ethylated <i>N</i>‐Vinyl‐2‐pyrrolidone with LCST Properties in Water

Trellenkamp, Taina; Ritter, Helmut

doi:10.1002/marc.200900250

Cited by 24 publications

(31 citation statements)

References 18 publications

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“…Especially polymers having a lower critical solution temperature (LCST) in water, like poly( N -isopropylacrylamide) or modified poly( N -vinylpyrrolidone) are extensively described in literature [4–5]. Below the critical temperature ( T C ) these polymers are soluble and they become insoluble by heating their solutions above the T C .…”

Section: Introductionmentioning

confidence: 99%

Influence of cyclodextrin on the UCST- and LCST-behavior of poly(2-methacrylamido-caprolactam)-co-(N,N-dimethylacrylamide)

Burkhart¹,

Ritter²

2014

Beilstein J. Org. Chem.

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SummaryThe monomer 2-methacrylamido-caprolactam (4) was synthesized from methacryloyl chloride (3) and racemic α-amino-ε-caprolactam (2). Copolymerization of 4 with N,N-dimethylacrylamide (5) was carried out by a free-radical mechanism using 2,2’-azobis(2-methylpropionitrile) (AIBN) as an initiator. The new copolymers show a lower critical solution temperature (LCST) in water and an upper critical solution temperature (UCST) in ethanol, 1-propanol, and 1-butanol. The solubility properties of the copolymers can be influenced significantly by the addition of randomly methylated β-cyclodextrin (CD). The complexation of the copolymers with CD, was confirmed by the use of ROESY-NMR-spectroscopy.

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Section: Introductionmentioning

confidence: 99%

Influence of cyclodextrin on the UCST- and LCST-behavior of poly(2-methacrylamido-caprolactam)-co-(N,N-dimethylacrylamide)

Burkhart¹,

Ritter²

2014

Beilstein J. Org. Chem.

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“…Thereby, the electron-rich double bond of N -VP is stable towards nucleophilic attack of the resulting carbanion intermediates. Some alkylated N -VP-based monomers can be used as agents in click chemistry [17] to obtain thermo- [18] or/and pH [19] responsive polymers. Besides classical alkylation reactions, Reinecke et al performed ring-opening reactions to insert functional groups and aromatic side chains [20–21].…”

Section: Introductionmentioning

confidence: 99%

From N-vinylpyrrolidone anions to modified paraffin-like oligomers via double alkylation with 1,8-dibromooctane: access to covalent networks and oligomeric amines for dye attachment

Obels

Lievenbrück

Ritter

2016

Beilstein J. Org. Chem.

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SummaryThe double alkylation of N-vinylpyrrolidone (N-VP) with 1,8-dibromooctane yields paraffin-like oligomeric chains bearing polymerizable vinyl moieties. These oligomers were radically crosslinked in bulk with N-VP as co-monomer yielding swellable polymer disks. The vinylic side groups of the N-VP oligomers allow thiol–ene click reactions with 2-aminoethanethiol hydrochloride to obtain reactive amino-functionalized oligomers. Further modification of the free amino groups with 1,4-difluoro-9,10-anthraquinone (DFA) yields red-colored oligomeric anthraquinone dyes. The final reaction of DFA-substituted N-VP oligomers with Jeffamine® M 600 leads to blue-colored and branched oligomers with poly(ethylene glycol) side chains.

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“…Since the double bond of N ‐VP is electron rich, nucleophilic displacement reactions can be performed without attacking the N ‐vinyl group. In this connection, we recently mono‐ethinylated N ‐VP to achieve lower critical solution temperature properties in water . We also attached cyclodextrin azide covalently to ethinylated N ‐VP via a click reaction .…”

Section: Introductionmentioning

confidence: 99%

Forgotten monomers: access to α‐modified N‐vinylpyrrolidone polymers via C‐alkylation

Obels

Siegfeld

Ritter

2015

Polymer International

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Alkylation of N‐vinylpyrrolidone using lithium diisopropylamide and bis(2‐bromoethyl) ether was carried out to obtain 3‐(2‐(2‐bromoethoxy)ethyl)‐1‐vinyl‐2‐pyrrolidone (2). The derivative 2 represents a versatile starting molecule for further modification via nucleophilic displacement yielding, for example, the bicyclic 2‐vinyl‐8‐oxa‐2‐azaspiro[4.5]decan‐1‐one (4) or the ammonium salt 3‐diethoxy‐N,N′‐((dimethylbenzyl)ammonium bromide)‐1‐vinyl‐2‐pyrrolidone (10). Via free radical polymerization of 4 and 10, the corresponding homopolymers were obtained. Copolymerization of 4 and 10 with N,N′‐diethylacrylamide yielded water‐soluble materials. The thermosensitive solubility of copolymers poly[(2‐vinyl‐8‐oxa‐2‐azaspiro[4.5]decan‐1‐one)‐co‐(N,N′‐diethylacrylamide)] and poly[(3‐diethoxy‐N,N′‐((dimethylbenzyl)ammonium bromide)‐1‐vinyl‐2‐pyrrolidone)‐co‐(N‐vinylpyrrolidone)] in water was investigated. © 2015 Society of Chemical Industry

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3‐Ethylated N‐Vinyl‐2‐pyrrolidone with LCST Properties in Water

Cited by 24 publications

References 18 publications

Influence of cyclodextrin on the UCST- and LCST-behavior of poly(2-methacrylamido-caprolactam)-co-(N,N-dimethylacrylamide)

Influence of cyclodextrin on the UCST- and LCST-behavior of poly(2-methacrylamido-caprolactam)-co-(N,N-dimethylacrylamide)

From N-vinylpyrrolidone anions to modified paraffin-like oligomers via double alkylation with 1,8-dibromooctane: access to covalent networks and oligomeric amines for dye attachment

Forgotten monomers: access to α‐modified N‐vinylpyrrolidone polymers via C‐alkylation

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