1-Butanol → Isophorone diisocyanate

Participants

Reaction Conditions

Reaction Steps

About 525.0 grams (4.73 equiv.) of isophorone diisocyanate8, about 1.5 grams of dibutyltindilaurate9 catalyst, and about 992.0 grams (3.91 equiv.) of octylphenol ethoxylate10 were added to a 3000 ml three-neck resin kettle equipped with a Trubore stirrer, a N2 atmosphere inlet, and a thermocouple-temperature controller. The reaction mixture was heated to about 135° C. and held for approximately 3.5 hours with stirring under nitrogen. About 240.6 grams (0.473 equiv.) of a cyan polymeric colorant11 were then added and the mixture was heated at about 150° C. for approximately 2 hours. An FT-IR of the product was obtained to insure all of the isocyanate (NCO) functionality was consumed. The absence (disappearance) of a peak at about 2285 cm-1 (NCO) and the appearance (or increase in magnitude) of peaks at about 1740-1680 cm-1 and about 1540-1530 cm-1 corresponding to urethane frequencies were used to confirm this. The diurethane reaction product was poured into aluminum molds and allowed to cool and harden. This final colored resin product was characterized by the following physical properties: viscosity of about 181.8 cPs as measured by a Ferranti-Shirley cone-plate viscometer at about 140° C., a melting point of about 59.9-70.2° C. as measured by electrothermal capillary melting point apparatus, and a Tg of about 23.1° C. as measured by differential scanning calorimetry using a DuPont 2100 calorimeter at a scan rate of 20° C./minute, and a spectral strength of about 5588 milliliters Absorbance Units per gram at λmax as measured by dilution in n-butanol using a Perking Elmer Lambda 2S UV/VIS spectrophotometer.

Provenance & Evidence