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3 protocols using Methanol

Acrylonitrile (>99%), acryloyl chloride (96%), dichloromethane (99.9%), methanol (99%), methyl acrylate (>99%), potassium carbonate (99%), sodium persulfate (98%), and triethyl amine (99%) were purchased from abcr GmbH (Karlsruhe, Germany). Sodium metabisulfite (99%), propylene carbonate (99%), iron (II) sulfate hydrate (>99%), and aluminum sulfate hydrate (98–102%) were purchased from Alfa Aesar (Kandel, Germany). Sulfuric acid (96%) was purchased by Acros Organics (Morris Plains, NJ, USA). Dimethyl phosphite (98%) was purchased from Sigma Aldrich (Darmstadt, Germany). All chemicals were used as received.
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The following materials
were used in this experiment: N-trimethoxysilylpropyl-N,N,N-trimethylammomium
chloride (hydrophilpos, 50% in methanol, ABCR, Germany),
chloroform (CHCl3, 99.0% purity, Wako Pure Chemical Industries,
Japan), methanol (MeOH, HPLC grade, Fisher Scientific, Germany), ethanol
(EtOH, JIS Special Grade, Wako Pure Chemical Industries, Japan), aqueous
ammonia solution [NH3(aq), 25 wt %, analytical grade, WTL
Laborbedarf GmbH, Kastellaun, Germany], BIEE (96% purity, Sigma-Aldrich),
and sodium hydroxide (NaOH, 97.0% purity, Wako Pure Chemical Industries,
Japan). Ultrapure water (Direct-Q 3 UV, Millipore, USA) with a specific
resistivity of 18.2 MΩ cm–1 was used in this
study. The PDMA−PS particles had 3.21 wt % poly(2-(N,N-dimethylamino)ethylmethacrylate) loading.
The diameter of the PDMA–PS particles was 333 ± 128 nm.
The details of the synthesis and preparation can be found elsewhere.7 (link),18 (link) The pH 5.8 and 9.0 aqueous solutions used as the subphases of the
particle films in this study were pure water and water adjusted to
pH 9.0 by the addition of NaOH. These subphases are referred to as
“pH 5.8 water” and “pH 9.0 water” throughout
this study.
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Ethylene glycol (EG, ≥99.5%) and disodium
hydrogen phosphate dihydrate (≥98%) were purchased from Carl
Roth, hexenedioic acid (HA, >98%) from TCI, maleic acid (MA, 99%)
and sodium dihydrogen phosphate monohydrate (≥99.99%) from
Merck, N-tertbutyl benzothiazole sulfonamide (TBBS)
and 2,2-dibutyl diethylmalonate (98%) from abcr, methanol (≥99.8%),
dibutyl tin oxide (DBTO), 2,6-di-tert-butyl-p-cresol (BHT, 99%), and 13C2–EG
(99 atom % 13C) from Sigma-Aldrich, and chloroform (≥99.8%)
from VWR. Deuterated solvents were obtained from Eurisotop and dried
over molecular sieves from Riedel-de Haën (0.4 nm). Pripol
1009 (dimer acid, DA, 98%) was kindly provided by Croda/Cargill.
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