Methacrylate → 2-Hydroxyethyl Methacrylate

HRID 1911798

Reaktionsgleichung

Reaktionsgleichung von HRID 1911798
C1C=CC(/C=C/C[O:10][C@@H:11]2[O:16][C@H:15]([CH2:17][OH:18])[C@@H](O)[C@H:13](O)[C@H:12]2O)=CC=1.[C:22]([O-])(=O)C(C)=C.CC(C1C=C2CC[C@H]3[C@@](C(O)=O)(C)CCC[C@]3(C)[C@H]2CC=1)C>S(Cl)(Cl)=O>[C:11]([O:16][CH2:15][CH2:17][OH:18])(=[O:10])[C:12]([CH3:13])=[CH2:22]

Komponenten

5

Edukt 3

HCID 87595Methacrylate2×HCID 221062Levopimaric acidHCID 5280656(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol

Produkt 1

HCID 133602-Hydroxyethyl Methacrylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

This example is to prepare quaternary ammonium-containing rosin-derived methacrylate polymers, according to the exemplary method shown in FIG. 2. The method involves the synthesis of methacrylate monomers containing Diels-Alder adduct (anhydride) by esterification, and homopolymer by free radical polymerization. Following the amidation and quaternization reactions, the quaternary ammonium group is introduced. A typical procedure for the synthesis is described as follows: levopimaric acid is dissolved in thionyl chloride and refluxed for 12 h. Thionyl chloride is removed by reduced pressure distillation. The methacrylate monomer containing Diels-Alder adduct (anhydride) 3 is obtained by the addition of excess 2-hydroxyethyl methacrylate (2-HEMA) and using triethylamine as catalyst. The homopolymer is prepared by the radical polymerization of monomer 3 in the presence of the toluene and azoisobutyronitrile (AIBN). The homopolymer is dissolved in ethanol and then added with the dimethylethylenediamine. The mixture is stirred at 85° C. for 5 h and precipitated in diethyl ether to obtain the rosin-derived tertiary ammonium homopolymer. The quaternary ammonium unit 4 is then introduced by the reaction between the rosin-derived tertiary ammonium homopolymer and alkyl halide (e.g. bromoethane, bromohexane, bromooctane and bromododecane) in tetrahydrofuran at 40° C. for 48 h.

Aufarbeitung

  1. customby free radical polymerization
  2. additionthe quaternary ammonium group is introduced
  3. temperaturerefluxed for 12 h
  4. customThionyl chloride is removed by reduced pressure distillation
  5. additionThe methacrylate monomer containing Diels-Alder adduct (anhydride) 3

Quellen und Nachweise

ORD-Eintrag
ord-60284e168453444fbd3f6f57f33a690b
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604128B2

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