Effect of structure on properties of polyols and polyurethanes based on different vegetable oils

We synthesized six polyurethane networks from 4,4-diphenylmethane di- isocyanate and polyols based on midoleic sunflower, canola, soybean, sunflower, corn, and linseed oils. The differences in network structures reflected differences in the composition of fatty acids and number of functional groups in vegetable oils and resulting polyols. The number average molecular weights of polyols were between 1120 and 1300 and the functionality varied from 3.0 for the midoleic sunflower polyol to 5.2 for the linseed polyol. The functionality of the other four polyols was around 3.5. Canola, corn, soybean, and sunflower oils gave polyurethane resins of similar crosslink- ing density and similar glass transitions and mechanical properties despite somewhat different distribution of fatty acids. Linseed oil- based polyurethane had higher crosslinking density and higher mechanical properties, whereas midoleic sunflower oil gave softer polyurethanes characterized by lower Tg and lower strength but higher elongation at break. It appears that the differences in properties of polyurethane networks resulted primarily from different crosslinking densities and less from the position of reactive sites in the fatty acids. © 2004 Wiley Periodicals, Inc. J Polym Sci Part B: Polym Phys 42: 809 - 819, 2004

[1]  K. Dušek,et al.  Structure and properties of triolein-based polyurethane networks. , 2002, Biomacromolecules.

[2]  E. Frankel,et al.  Rigid urethane foams from hydroxymethylated castor oil, safflower oil, oleic safflower oil, and polyol esters of castor acids , 1974 .

[3]  Zoran S. Petrović,et al.  Epoxidation of soybean oil in toluene with peroxoacetic and peroxoformic acids — kinetics and side reactions , 2002 .

[4]  E. Frankel,et al.  Rigid urethane foams from hydroxymethylated linseed oil and polyol esters , 1972 .

[5]  Y. Cho,et al.  Structure and properties of halogenated and nonhalogenated soy‐based polyols , 2000 .

[6]  J. Crivello,et al.  Epoxidized triglycerides as renewable monomers in photoinitiated cationic polymerization , 1992 .

[7]  D. V. Krevelen Properties of Polymers , 1990 .

[8]  A. N. Wrigley,et al.  Urethane foams from animal fats: V. Flame resistant foams from hypohalogenated glycerides , 1970 .

[9]  G. Maerker,et al.  Acid-catalyzed conversion of epoxyesters to hydroxyesters , 1964 .

[10]  Wei Zhang,et al.  Structure and properties of polyurethanes based on halogenated and nonhalogenated soy–polyols , 2000 .

[11]  A. Hautfenne Standard methods for the analysis of oils, fats and derivatives, 6th Edition. 1st Supplement: Part 5 (1982) Section III, Glycerines. Section IV, Alkaline soaps , 1982 .

[12]  A. Bilyk,et al.  Urethane foams from animal fats: IX. Polyols based upon tallow and trimethylolpropane; preparation under acidic and basic catalysis , 1975 .

[13]  A. N. Wrigley,et al.  Urethane foams from animal fats. IV. Rigid foams from epoxidized glycerides , 1968, Journal of the American Oil Chemists' Society.

[14]  I. Javni,et al.  Rigid polyurethane foams based on soybean oil , 2000 .

[15]  M.J.R Blackman Rembrandts in the Attic: Unlocking the Hidden Value of Patents: Kevin G. Rivette and David Kline; Harvard Business School Press, Boston, Massachusetts, 2000, ISBN 0-87584-899-0 , 2000 .

[16]  C. P. Tan,et al.  Differential scanning calorimetric analysis of edible oils: Comparison of thermal properties and chemical composition , 2000 .

[17]  E. H. Pryde,et al.  The acid-catalyzed addition of alkoxyl groups to the olefinic double bonds of soybean oil , 1988 .

[18]  B. Dahlke,et al.  Polyhydroxy fatty acids and their derivatives from plant oils , 1995 .