The esterified mixture was analyzed by gas-liquid chromatography (glc) and run isothermally at 180°C for a short period to determine monomer content and then linear temperature programmed to 360°C at 30°C/min with an airoxidized silicone column developed especially for the analysis of rosin-dimeric dibasic acids (Sinclair et al., 1970) (4.5-ft X */i6-in., stainless steel, 3%, SE 52 on Gas-Chrom Q, cured in air at 350°C overnight). The yields based on dehydroabietic acid were dibasic acid dimers, 62%, methyl dehydroabietate, 38%, calculated from the glc volatile material. The total percent glc volatiles was 80%. The yield of dimer based on Literature Cited
9-Aminononanamide, a potential intermediate for nylon-9, was prepared from soybean oil via alkyl soyate, aldehyde oil or soybean amides. All three routes involved various sequences for reductive ozonolysis, reductive amination and ammonolysis. The preferred route is through the alkyl soyatcs, although the other two have fewer steps. The amino amide is a water-soluble, strongly basic solid that rapidly absorbs atmospheric carbon dioxide and is readily hydrolyzed to 9-aminononanoic acid. Although the amino amide is selfpolymerizable in limited degree, the preferred monomer for nylon-9 is the amino acid. Other new compounds prepared and characterized include azelaaldehydamide, bis(8-carbamoyloctyl) amine ; N-( 8 -c a r b a m o y 1 o c t y 1) -8 -methoxycarbonyloctylamine ; 9-hydroxynonanamide ; and dimers of the amino amide and the amino ester.
Catalysts for the ammonolysis of soybean oil are, in order of decreasing overall effectiveness, ammonium acetate, sodium metlioxide, 9-aminononanoic acid, sodium soyate, ammonium nitrate, alanine, sodium acetate and glycerol. At 125 C, a reaction time of 1 hr and a 30:1 mole ratio of ammonia to ester, ammonium acetate achieved ammonolysis in 16%, 61% and 84% conversions at the respective concentrations of 0.0, 0.1 and 1.0 mole per mole ester groups. Conversion was 98% complete in 4 hr with 1.0 mole. The ammonolysis generally exhibited the expected first order kinetics up to about 80% reaction.
AND SUMMARYA series of polyamide and copolyamide resins were prepared from carboxystearic acid or methyl carboxystearate, with ethylenediamine, hexamethylenediamine, adipic acid, or caprolactam as coreactants. None of the product formulations appeared suitable for use in hot melt adhesives. More promising were the liquid, reactive polyamides made from carboxystearic acid and polyamines. These products gave excellent adhesion value in scouting tests when used as one component in 2-component epoxy adhesives and coatings. In other applications, C-19 polyamides had enhanced solubility and low melting characteristics to make them attractive as modifiers.
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