Polyesteramides from linseed and soybean oils for protective coatings: Diisocyanate‐modified polymers

Abstract

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.

Catalytic polymerization of N,N-diethanol acrylamide with phthalic anhydride in the presence of H-mordenite and Fe-mordenite zeolites

“…The formation of 100% amide in the absence of any catalyst and in presence of some oxide catalysts such as Fe 2 O 3 and TiO 2 ; as has been evidenced by some authors [1][2][3][4][5][6], provokes the importance of the unshared electron pair on the amine nitrogen; which can be shared with electron deficient carbonyl group. Such unshared pair on nitrogen is less tightly held than that on the corresponding oxygen atom of alcohol based on electronegativity consideration.…”

“…The analyses were accomplished by means of a Perkin-Elmer Lambda 3 spectrophotometer. 1 H NMR spectra were measured on a Varian Gemini (300 MHz) instrument.…”

“…The reaction proceeds to completion in forming DEAA and DEMA with selectivities 91 and 9%, respectively. It is noteworthy mentioning that the majority of the work used to prepare dihydric amino alcohol derivatives of fatty acids claimed the absence of the ester formation [1][2][3][4][5][6].…”

“…Polymeric systems based on polyesteramides (PEA) are high performance material, which combine the useful properties of polyester and polyamide resins, and finds many applications most importantly as protective surface coatings [1,2]. Diethanolamine derivatives of fatty acids were used in the preparation of polyesteramide and alkyd/polyesteramide resins [3,4].…”

Seed Oil Based Polyurethanes: An Insight

“…In SO based PU, although SO have ester groups susceptible to hydrolysis, long hydrophobic fatty acid chains cause shielding effect. Under highly humid conditions, urethane bonds undergo hydrolysis producing amine and carbon dioxide [1,19].…”