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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

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ABSTRACT

The 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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Chemical structure of water swellable network 3a and 3b. Photographs of water-swollen polymer disks consisting of 1 mol % (3a) and 2.5 mol % (3b) of 2a as cross linker.
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Figure 1: Chemical structure of water swellable network 3a and 3b. Photographs of water-swollen polymer disks consisting of 1 mol % (3a) and 2.5 mol % (3b) of 2a as cross linker.

Mentions: The vinylic groups of 2a can easily be radically copolymerized in bulk with a molar excess of N-VP. By using either 1.0 mol % (Fig. 1) or 2.5 mol % of 2a in relation to N-VP, two different cross-linked polymers 3a,b were obtained as disks showing a certain swelling behavior in distilled water (Fig. 1).


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
Chemical structure of water swellable network 3a and 3b. Photographs of water-swollen polymer disks consisting of 1 mol % (3a) and 2.5 mol % (3b) of 2a as cross linker.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4979690&req=5

Figure 1: Chemical structure of water swellable network 3a and 3b. Photographs of water-swollen polymer disks consisting of 1 mol % (3a) and 2.5 mol % (3b) of 2a as cross linker.
Mentions: The vinylic groups of 2a can easily be radically copolymerized in bulk with a molar excess of N-VP. By using either 1.0 mol % (Fig. 1) or 2.5 mol % of 2a in relation to N-VP, two different cross-linked polymers 3a,b were obtained as disks showing a certain swelling behavior in distilled water (Fig. 1).

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The 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.

No MeSH data available.


Related in: MedlinePlus