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7 protocols using decalin

1

Synthesis of Maleated Copolymers

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The reference ethylene/propylene
copolymer (EPM, Keltan 1500R, 49 wt % ethylene) and ethylene/vinyl
acetate copolymer (EVM, Levamelt 700, 30 wt % ethylene, Mn = 35 kg/mol, PDI = 9) and the analogous, maleated EPM
(EPM-g-MA, Keltan DE5005, 48 wt % ethylene, 50 wt
% propylene, 2.1 wt % MA) and maleated EVM (EVM-g-MA, 30 wt % ethylene, 69 wt % vinyl acetate, 1.4 wt % MA) were kindly
provided by ARLANXEO Performance Elastomers. The EPM-g-MA and EVM-g-MA precursors were dried in a vacuum
oven at 175 °C for 1 h to convert any diacid present into the
cyclic anhydride.2 (link),17 (link) Furfurylamine (FFA, Sigma-Aldrich,
≥99%) was freshly distillated before use. 1,1-(Methylenedi-4,1-phenylene)bismaleimide
(BM, 95%), octadecyl-1-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate
(99%), dicumyl peroxide (DCP, 98%), tetrahydrofuran (THF, >99.9%),
toluene (99.8%), decalin (mixture of cis and trans, 98%), and acetone
(>99.5%) were all purchased from Sigma-Aldrich and used as received
as reversible cross-linker, antioxidant, peroxide cross-linker, and
solvents, respectively.
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2

Activated Carbon-Supported Metal Catalysts

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EXAMPLE 1

Materials

Activated carbon (AC) derived from waste tires, ammonium molybdate [(NH4)6Mo7O24.4H2O], nickel acetate [Ni(C2H3O2)2.4H2O], cobalt nitrate [Co(NO3)2.6H2O], decahydronaphthalene (Decalin) [C10H18], dibenzothiophene (DBT) [C12H8S], citric acid (CA) [C6H10O7], ethylenediaminetetracetic acid (EDTA) [C10H16N2O8], and deionized water [H2O].

The ammonium molybdate, nickel acetate, and cobalt nitrate were A.C.S certified analytical grades from Fisher Scientific Company, USA. Decalin (99%) and DBT (98%) were obtained from Sigma Aldrich. All the reagents were used as purchased from the manufacturers without any form of pretreatment or modification.

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3

Polymer Fractionation and Crude Oil Analysis

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Commercially available Torlon® 4000T-LV and Matrimid®5218 were purchased from Solvay Advanced Polymers (Alpharetta, GA) and Huntsman, respectively. SBAD-1, DUCKY-9, and DUCKY-10 polymers were synthesized from literature procedures detailed in two previous publications4 ,5 (link). Two real crude oils (Permian and Arabian light crude oils) were provided from ExxonMobil Technology and Engineering Company. The experimental results of the two fractionations were published previously4 ,5 (link). All other chemicals (p-xylylene diamine, lithium nitrate, chloroform, tetrahydrofuran, 1-methylpyrroldone, ethanol, methanol, hexane, toluene, toluene, Tert-butyl benzene, 1,3,5-triisopropyl benzene, n-Octane, iso-Octane, iso-cetane, methylcyclohexane, decalin, 1-methylnaphthalene, o-xylene, propyl benzene, mesitylene, n-butylcyclohexane, tetralin, bi-phenyl, dodecylbenzene, 1,3,5-triphenylbenzene, 1,3,5-Tris[(3-methylphenyl) phenylamino]benzene), methanol, and guaiacol were purchased from Sigma Aldrich, Alfa Aesar, or TCI and used as received.
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4

Photocurable 5Y-PSZ Suspension for Dental Crowns

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Table 1 summarizes the constituents of photocurable 5Y-PSZ suspensions with a solid loading of 50 vol% used for manufacturing dental crowns by our DLP process. Unless otherwise notified, all reagents were used as purchased. To obtain reasonably low viscosities at high solid loadings, 1,6-hexanediol diacrylate (HDDA; Sartomer, Exton, PA, USA) and decalin (Sigma Aldrich, St. Louis, MO, USA) were employed as the photopolymerizable monomer and diluent, respectively [26 (link)]. An alkylol-ammonium salt of a copolymer with acidic groups (DISPERBYK-180; BYK-Chemie GmbH, Wesel, Germany) was used as a dispersant. Diphenyl(2,4,6-trimethylbenzoyl) phosphine oxide (TPO; Sigma Aldrich, St. Louis, MO, USA) was used as a photo-initiator.
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5

Synthesis of Graphene-Reinforced Polymers

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Graphite (+100 mesh (≥75% min)), polyetherimide (melt index 18 g/10 min (337 °C/6.6 kG)), and barium titanate (IV) nanopowder (cubic) 50 nm 99.9% were supplied by Aldrich. Nitric acid (≥99.0%), potassium chlorate (≥99.0%), (3-aminopropyl) triethoxysilane (APTES) (≥98.0%), α-bromoisobutyryl bromide (BIBB) (98.0%), triethylamine (≥98.0%), N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDETA, 99%), ascorbic acid (≥99.0%), decalin (decahydronaphthalene, mixture of cis + trans) (98%), dichloromethane, N,N-dimethylformamide (DMF), sulfuric acid (95–97%) and sodium nitrate were supplied by Sigma-Aldrich. Potassium permanganate and copper (II) bromide were obtained from Merck.
Monomethyl itaconate (MMI) [21 (link)], graphene oxide (GO) [16 (link)], reduced graphene oxide (rGO) [16 (link)], and poly (monomethyl Itaconate) grafted graphene oxide (GO-g-PMMI) [16 (link)] was synthesized using the previously reported method.
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6

Suzuki Synthesis of Polystyrene-Equivalent PFO

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PFO, synthesized by Suzuki coupling, was supplied by Cambridge Display Technology and used as received. The sample used for this study had a polystyrene-equivalent gel permeation chromatography measured number average molecular weight Mn=28 × 103 g mol−1, with polydispersity index=2.93. Decalin (decahydronaphthalene; anhydrous, ≥99%, mixture of cis and trans isomers) and IPA (anhydrous, 99.5%) were purchased from Sigma-Aldrich; HPLC-grade cyclohexane (≥99.9%) and toluene (≥99.7%) were purchased from VWR. All solvents were used as received.
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7

Synthetic Reagent Preparation Protocol

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Chemicals were purchased from the following companies: Dichloromethane (99 + %), chloroform (99.8%), pentane (99.0%), decalin (98%, cis and trans), methanol (99.8%), benzyl chloride (99%) and SnCl4 (99%) from Sigma-Aldrich (Buchs, St.Gallen, Switzerland); AgSO3CF3 (99%) from Fluorochem (Hadfield, Glossop, UK); AgClO4 (97%) and [Cr(CO)6] (99%) from ABCR (Kasru, Baden-Wuerttemberg, Germany); and dry THF (99.5%) over a molecular sieve from Fisher Scientific (Schwerte, Nordrhein-Westfalen, Germany). All chemicals were used as received.
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