Tetraethylenepentamine

Dimer acid cyclic carbonate (DACC) was synthesized based on our previous work (GC/DA molar ratio 8.00, reaction time 12 h, enzyme loading 8% (wt %, w/w DA), reaction temperature 50 °C, molecular sieves content 0.6 (wt, w/w DA), agitation speed 200 rpm and acetonitrile as the solvent) [18 ]. NIPU-23, NIPU-34, and NIPU-45 were, respectively, synthesized from DACC with dithylenetriamine, triethylenetetramine and tetraethylenepentamine (Scheme 2, solution polymerization, reaction time 12 h and reaction temperature 90 °C). Absolute ethyl alcohol, dichloromethane, dimethylsulfoxide (DMSO), diethylenetriamine (DETA), triethylenetetramine (TETA), and tetraethylenepentamine (TEPA) were of analytic reagents and were bought from Sinopharm Chemical Reagent Ltd., Co. (Shanghai, China). Bisphenol-A epoxy resin E-44 (mean epoxy value: 0.44) and Bisphenol-A epoxy resin E-51 (mean epoxy value: 0.51) were purchased from Yueyang Petrochemical Ltd., Co. (Yueyang, China). All of the materials were used as received without any further purification.

Divinylbenzene (DVB, 80 wt.%), methylacrylate (MA, >99%), benzoyl peroxide, and TC were obtained from J&K Chemical Co., Ltd., China. Tetraethylenepentamine, anhydrous ferric chloride, 1,2-dichloroethane, sodium chloride, hydrochloric acid, sodium hydroxide, and cupric nitrate trihydrate were all analytical reagents and purchased from Sinopharm Chemical Reagent Co., Ltd (China). DVB and MA were passed through a strong base anion exchange resin column to remove the inhibitors prior to use.

Iron pentacarbonyl [Fe(CO)₅, 98%], 1-octadecene (ODE, 90%) and oleylamine (OLA, 90%) were purchased from Aladdin reagent company (Shanghai, China). Absolute ethanol (99.7%) and tetraethylenepentamine (TEPA, 90%) were purchased from Sinopharm Chemical Reagent Co. Ltd. (Shenyang, China). Prior to synthesis, the original TEPA was heated to 588 K in a nitrogen atmosphere and kept at this temperature for 5 h. Other chemicals were used without further purification.