Patent GB-979667-A (GB)
Title: Nitrogen and hydroxyl containing ester adducts and the production of polyurethanes
Inventor: TURNER ROBERT JOHN
IPC: C08G18/38
Filed: 1962-05-23
Abstract: Novel adducts are produced by reacting an epoxy ester of the general formula <FORM:0979667/C1/1> with a mono or di-alkanolamine in the mol. ratio of 0.5 to 2.0:1 of epoxy ester to monoalkanolamine and 0.5 to 1.0:1.0 epoxy ester to dialkanolamine, where R1 and R2 are similar or dissimilar alkyl groups and R3 to R8 each are hydrogen or an alkyl group, especially those compounds wherein all R4 to R8 are hydrogen. A preferred adduct is one wherein the acid comprising the epoxy ester is obtained by reacting an olefin, preferably of six to eighteen carbon atoms, with carbon monoxide and water in the presence of a highly acidic compound. From the alkanolamines the dialkanolamines are preferred, especially diethanolamine and diisopropanolamine. The products are suitable for conversion to polyurethanes (see Divisions B2, C3).  In the example a paraffin feedstock is cracked to an alkene, which is converted to monoenes which are converted to give C9 to C11 saturated monocarboxylic acids by adding carbon monoxide and water in the presence of phosphoric acid and boron trifluoride. One mole of the sodium salt of the above acid is reacted with epichlorohydrin to give the glycidyl ester which is then heated with one mole of diethanolamine to give the novel product. Specifications 743,579, 798,065, 871,278, 883,142 and 936,808 also are referred to.ALSO:Polyurethanes are obtained by reacting a novel adduct of an epoxy ester of the general formula <FORM:0979667/C3/1> and a mono or dialkanolamine (see Division C2) and an organic polyiso or isothiocyanate, especially the diisocyanate and particularly 4, 41-diisocyanate-diphenyl methane. R1 and R2 may be similar or dissimilar alkyl groups, R3 to R8 may each be hydrogen atoms or alkyl groups, the preferred type having R4 to R8 all hydrogen atoms, the alkanolamine, preferably dialkanolamine being diethanolamine or diisopropanolamine. Extenders i.e. coal tar, pitch, transformer or pine oil, coumarone resins, solvent extracted lubricating oil, fillers such as barytes, mica slate powder, silica flour may be admixed. Extensive lists of di-isocyanates are given and include "mashed" types. In the examples stannous octoate is included as a catalyst to promote curing.  Specifications 743,597, 798,065, 871,278, 883,142 and 936,808 also are referred to.ALSO:Metals may be coated with a polyurethane see Division C3) product made from a novel see Division C2) adduct of an epoxy ester and a mono- or dialkanolamine and a poly-iso or isothiocyanate, diluted or extended with coal tar, pitch, pine or transformer oil, a coumarone resin or a solvent extracted lubricating oil distillate and optionally filled, e.g. with barytes, mica, slate powder or silica flow.  In an example the glycidyl ester of mixed C9-C11 acids reacted with diethanolamine, mixed with a solvent extracted aromatic cut has stirred into it 4,41-diisocyanatodiphenyl methane, the reacting mass being coated on to shot blasted steel panels and /  cured at room temperature. Specifications 743,597, 798,065, 871,278, 883,142, and 936,808 also are referred to.