Dibutylamine (DBA) is a colorless, oily liquid organic compound with a characteristic amine odor. It is a secondary amine with the chemical formula (C₄H₉)₂NH. DBA is commonly used as a chemical intermediate and reagent in various industrial and laboratory applications.
The 4,4′-methylene diphenyl diisocyanate (MDI) and a mixture (about 80:20) of 2,4- and 2,6-toluene diisocyanates (TDI) were provided by Elantas Europe S.r.l. and stored at − 18 °C. Reagent grade triethylamine (TEA), benzylamine (BA) and dibutylamine (DBA) were purchased from Sigma Aldrich. Acetone-d6 was purchased from Sigma Aldrich. HPLC water was purified using the Milli-Q system. HPLC grade acetonitrile was purchased from Sigma Aldrich. Technical grade acetonitrile and n-hexane were purchased from Carlo Erba. Technical grade dry tetrahydrofuran (THF) was purchased from Sigma Aldrich. Three batches of PA were provided by Elantas Europe S.r.l. Samples have a mean viscosity of 1100 mPa s and a mean dry content of 22.9% (solvent used is NMP). Three samples were chosen corresponding to three batches produced over a year (Table 1). One batch was marked as anomalous as slightly greater quantities of MDI and TDI were added during the condensation step of the synthesis process to achieve final specifications.
PAs sample provided by Elantas Europe S.r.l.
Sample name
Production date
Abnormality
PA 1
August 2020
Yes
PA 2
January 2021
None
PA 3
April 2021
None
The molecular structures of the standards were confirmed by 1H-NMR, recorded on a Varian Mercury plus 400 system at 400 MHz25 (link),26 (link).
Pastore G., Gabrielli S., Leone E., Cortese M., Gentili D., Biondi G, & Marcantoni E. (2022). A novel treatment and derivatization for quantification of residual aromatic diisocyanates in polyamide resins. Scientific Reports, 12, 12993.
Fatty Acid Methyl Ester of Very High Oleic Sunflower Oil (FAMEVHOSO) with 3.32 mmol double bond/g was kindly supplied by the ITERG group (Canéjan, France). The FAMEVHOSO is composed of 83% of oleic acid. Table S1 presents the distribution of fatty methyl esters of unsaturated FAMEVHOSO. Glacial acetic acid (AA), toluene (99%), H2O2 30%, ethyl acetate (99%), and ethanol (99.9%) were obtained from Fisher Scientific (Illkirch-Graffenstaden, France). Amberlyst® 15H (strongly acidic cation exchanger dry), Amberlite® IR120H (strongly acidic hydrogen form), CDCl3, phenylisocyanate (98%), dibutylamine (DBA) (99.5%), HBr (48% in water), HCl (37% in water), and diethylamine (99%) (DEA) were provided by Sigma-Aldrich (Saint-Quentin-Fallavier, France). ethanol absolute (EtOH) was purchased from VWR (Briare, France). All of the chemicals were used without any purification.
Peyrton J., Chambaretaud C, & Avérous L. (2019). New Insight on the Study of the Kinetic of Biobased Polyurethanes Synthesis Based on Oleo-Chemistry. Molecules, 24(23), 4332.
Acetonitrile (HPLC grade, 99.9%) and toluene (HPLC grade, 99.9%) was purchased from Fischer Scientific (Loughborough, UK). Mobile phase A was prepared using ultrapure water obtained from a Millipore Milli-Q Gradient A10 system (Millipore, Bedford, MA, USA). Formic acid (≥95%), dibutylamine (DBA) (≥99.5%) and non-deuterated as well as deuterated labelled (d9-or d18-labelled) isocyanate standard mixtures, see Online Supplementary Material, were purchased from Sigma-Aldrich (Steinheim, Germany).
Bengtström L., Salden M, & Stec A.A. (2018). Stability of Isocyanates Sampled in Fire Smokes. Annals of work exposures and health, 62(9).
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