Triglyceride oil-derived water-dispersible urethane resin coatings

Claim 1

A method of preparing water-dispersible urethane resin coating compositions comprising the following steps: a. amidating a drying or semidrying triglyceride oil with a diolamine in an oil:amine ratio of about 1:2 to yield a mixture of 2-monoglycerides and N,N-bis hydroxyalkyl fatty amides in a 2-monoglyceride:N,N-bis fatty amide ratio of approximately 1:2; b. reacting the mixture of 2-monoglycerides and N,N-bis hydroxyalkyl fatty amides from step (a) with a sufficient amount of an anhydride under sufficient conditions to convert a portion of said 2-monoglycerides and said N,N-bis hydroxyalkyl fatty amides to the corresponding 2-monoglyceride and N,N-bis hydroxyalkyl fatty amide half esters and to provide an acid value in the range of about 30-70 in said urethane resin coating compositions; c. neutralizing unesterified anhydride carboxyl groups on said 2-monoglyceride and N,N-bis hydroxyalkyl fatty amide half esters from step (b): d. reacting the resultant 2-monoglyceride, 2-monoglyceride half ester, N,N-bis hydroxyalkyl fatty amide, and N,N-bis hydroxyalkyl fatty amide half ester mixture from step (c) with a diisocyanate in a molar ratio of diisocyanate:2-monoglyceride +N,N-bis-hydroxyalkyl fatty amide of from about 0.85:1 to about 0.58:1, thereby polymerizing the components of said mixture into a urethane resin; and e. recovering said urethane resin prepared in step (d).

Claim 2

A method of preparing water-dispersible urethane resin coating compositions comprising the following steps: a. amidating a drying or semidrying triglyceride oil with a diolamine in an oil:amine ratio of about 1:2 to yield a mixture of 2-monoglycerides and N,N-bis hydroxyalkyl fatty amides in a 2-monoglyceride:N,N-bis fatty amide ratio of approximately 1:2; b. reacting the mixture of 2-monoglycerides and N,N-bis hydroxyalkyl fatty amides from step (a) with a sufficient amount of an anhydride under sufficient conditions to convert a portion of said 2-monoglycerides and said N,N-bis hydroxyalkyl fatty amides to the corresponding 2-monoglyceride and N,N-bis hydroxyalkyl fatty amide half esters and to provide an acid value in the range of about 30-70 in said urethane resin coating compositions; c. neutralizing unesterified anhydride carboxyl groups on said 2-monoglyceride and N,N-bis hydroxyalkyl fatty amide half esters from step (b): d. reacting the resultant 2-monoglyceride, 2-monoglyceride half ester, N,N-bis hydroxyalkyl fatty amide, and N,N-bis hydroxyalkyl fatty amide half ester mixture from step (c) with a diisocyanate in a molar ratio of diisocyanate:2-monoglyceride +N,N-bis-hydroxyalkyl fatty amide of from about 0.85:1 to about 0.58:1, thereby polymerizing the components of said mixture into a urethane resin; and e. recovering said urethane resin prepared in step (d).