Epichlorohydrine

A native cellulose material with a degree of polymerization (DP) of 10,000, ferric chloride, copper chloride, nickel nitrate, sodium borohydride, isopropanol, H₂SO₄ (98%), epichlorohydrine (98%) and ammonium hydroxide (37%) was purchased from Sigma-Aldrich Co., St. Louis, MO, USA. 3-Chloro-2-hydroxypropyl amine was set up as per Ross et al. [25 (link)]. Other chemical reagents of analytical grade were also used.

Briefly, 4-aminophenyl disulfide (4-AFD) was purchased from Molekula (Rimini, Italy). Vanillyl alcohol (98%), phloroglucinol (99%), epichlorohydrine (99%), benzyltriethylammonium chloride (TEBAC, 99%), anhydrous sodium sulfate (Na₂SO₄, 99%), sodium hydroxide pellets (NaOH), and all used solvents (ethyl acetate, dichloromethane) (>95%) were purchased from Sigma Aldrich (Saint-Quentin Fallavier, France). Tetraethylammonium bromide (TEAB, 98%) was purchased from Alfa Aesar (Kandel, Germany). Supersap CLR epoxy resin system was purchased from Entropy Resins (Cupertino, CA, USA). All reagents, reactants and solvents were used as received (Figure 1).

Dichloromethane (DCM, analytical grade, Carlo Erba, Barcelona, Spain), acetone (analytical grade, Carlo Erba, Italy), sodium hydrogen carbonate (NaHCO₃, ≥95% purity, Sigma-Aldrich, St. Louis, MO, USA), tetrabutylammonium hydrogen sulfate (Bu₄NHSO₄, ≥97% purity, Fluka, Chemie, GmbH, Buchs, Switzerland), epichlorohydrine (99% purity, Sigma-Aldrich), and Oxone^® (Sigma-Aldrich) were purchased and used as received. Natural isoeugenol (Sigma-Aldrich, 99%), diglycidyl ether of bisphenol A (DGEBA, Sigma-Aldrich, Steinheim, Germany), camphoric anhydride (CA, 98% purity, Alfa Aesar, Ward Hill, MA, USA), hexahydrophtalic anhydride (HHPA, 95% purity, Sigma-Aldrich) and 1,2-dimethylimidazole (DMID, 95% purity, Sigma-Aldrich) were purchased and used without any further purification. These reagents are depicted in Scheme 1.