The sodium alkoxide‐catalyzed reaction of linseed oil or linseed methyl esters with diethanolamine produces almost exclusively linseed diethanolamides. Reaction conditions, e.g., temperature, amount of excess diethanolamine and mode of adding reactants, are reported. The best conditions for producing diethanolamide directly from linseed oil (1 mole) required adding oil to the sodium alkoxide in diethanolamine (6 moles) and heating at 110舑115C for 35 min. The linseed diethanolamide isolated in 93舑95% yield was an amber oil. Progress of the reaction, followed by thin‐layer chromatography, showed only trace amounts of byproducts. Polyester amides were prepared by heating linseed diethanolamide in refluxing xylene with dibasic acids or anhydrides, e.g., azelaic, maleic, fumaric, phthalic, terephthalic, itaconic, brassylic and dimer acids. Molecular weight, viscosity and film properties (air‐dried and baked) of the polyester amides were determined.

Linseed and soybean diethanolamides, from the sodium alkoxide‐catalyzed reaction of the corresponding oil with diethanolamine, were used as diols to prepare a series of polyesteramides. The diols and dibasic acids or anhydrides were heated in refluxing xylene until the theoretical amount of water was collected in a trap. Low acid‐value linseed polymers were prepared with 10, 20, and 30 mole percent excess diol over the dibasic acid, and the effect of the excess diol on molecular weight, viscosity, and film properties of the polymers was examined. Polyesteramides which contained 10 mole percent excess fatty diethanolamide were made with 11 dibasic acids or anhydrides. The polymers were brown‐orange oils with Gardner viscosities of Z7 to >>Z10. Number‐average molecular weights ranged from 2,200 to 5,200. Data on drying characteristics, hardness, and chemical resistance of films were obtained. The better polymers air‐dried rapidly to give hard, glossy films (Sward rocker 20–60). Films baked at 190C for 10 min were softer than the corresponding air‐dried films. Xylene resistance of soybean and linseed polymer films was generally excellent, and alkali resistance was moderate. Soybean films showed the better alkali resistance.

Two heat-bodied linseed oils, with Gardner viscosities of 37 and 55 rain, were saponified, converted to their methyl esters, and separated into 2 fractions with urea and . methanol. Gas-liquid chromatography showed the adduet fraction, which comprised 38-41% of the total methyl esters, to contain: pahnitie, stearic, oleic, "linoleic," and trace amounts of "linolenic" acid. The nonadducting fraction (59-62%) of the total methyl esters was separated by molecular distillation at 140C/7 ~ into a distillate and residue. The distillate amounted to 18-25% of the total methyl esters and had an iodine value ([.V.) of 142-145; its absorption at 232 m~ indicates 2.5-3.0% conjugated diene. Hydrogenation of this distillate gave a liquid product with an iodine number of 4 and a pour point of -50C. Gas chromatograms of the distillate and its hydrogenated derivative indicated at least 5-7 components. Comparison of these peaks with known fatty acid methyl esters indicates that the components of these fractions were either cyclic or branched esters. The nonadducting residue fraction was composed mainly of polymeric acids.

Adducts of trans,trans-9,11-octadecadienoic acid and dienophiles including nitroethylene, /3-nitrostyrene, acrylic acid, acrylonitrile, acrolein, methacrolein, methyl vinyl ketone, methyl vinyl sulfone, and acetylene carboxylic acid have been prepared. The presence of a six-membered ring in the adducts of acrolein, acrylic acid, and acetylene carboxylic acid was demonstrated by dehydrogenation of the latter adduct and oxidation of the product to trimellitic acid. Hydrogenation of the acrylic acid and the acetylene carboxylic acid adduct gave the same product. Oxidation of the acrolein adduct gave the acrylic acid adduct. The nitroethylene adduct has been shown to exist in two isomeric forms.

New polymeric coating materials have been prepared by a triethylenediamine‐catalyzed reaction of hydroxyl‐terminated polyesteramides (HTPA) from soybean or linseed oils with diisocyanates. Eight dibasic acids or anhydrides were reacted with excess N,N‐bis(2‐hydroxyethyl) fatty amide to yield HTPA; those containing 10 mole per cent excess gave isocyanate‐modified polymers with best overall film properties. Reactivity of four diisocyanates with a linseed‐HTPA was measured by disappearance of the isocyanate band in the infrared. Depending on chemical composition, structure and curing conditions, films prepared from these polymers have a wide range of drying characteristics, hardness and chemical resistance. Drying times of linseed HTPA‐urethane polymer films varied from 0.3 to 48 hr, hardness values (Sward) were from 4 to 70, alkali resistance ranged from 2 to 126 min and the hydrochloric acid and xylene resistances were good to excellent. Impact resistance exceeded 160 in.‐lb for all films except two. The soybean‐derived polymer films likewise exhibited a wide range of properties; they chiefly differed from linseed‐derived films in having greater flexibility and improved alkali resistance.