Hydroxy functional alkyl polyurea crosslinkers
Abstract
A hydroxy functional alkyl polyurea is disclosed having the formula presented in claim 1, wherein R comprises an isocyanurate moiety, biuret moiety, allophonate moiety, glycoluril moiety, benzoguanamine moiety, polyetheramine moiety, and/or polymeric moiety different from a polyetheramine and having an Mn of 500 or greater; wherein each RI is independently a hydrogen, alkyl having at least 1 carbon, or a hydroxy functional alkyl having 2 or more carbons and at least one R1 is a hydroxy functional alkyl having 2 or more carbons; and n is 2-6. Further disclosed is a coating comprising: a film-forming resin; and a hydroxy functional alkyl polyurea crosslinker having the formula presented in claim 4, wherein R2 is a substituted or unsubstituted C1 to C36 alkyl group, an aromatic group, an isocyanurate moiety, biuret moiety, allophonate moiety, glycoluril moiety, benzoguanamine moiety, polyetheramine moiety, and/or polymeric moiety different from a polyetheramine having an Mn of 500 or greater, wherein each R1 is independently a hydrogen, an alkyl having at least 1 carbon, or a hydroxy functional alkyl having 2 or more carbons and at least one R1 is a hydroxy functional alkyl having 2 or more carbons; and n is 2-6, and when R2 is a substituted or unsubstituted C1 to C36 alkyl group the film-forming resin comprises COOH functionality that reacts with the polyurea to form an ester linkage.Other hydroxy functional alkyl polyurea compounds, polymers made with the same, and compositions comprising the same are also disclosed as are substrates coated at least in part with or formed with any of the compositions described herein.
Claims
exact text as granted — not AI-modified1 - 20 . (canceled)
21 . A thermoset composition, comprising:
(a) a hydroxy functional alkyl polyurea crosslinker having the formula:
wherein R 2 is a substituted or unsubstituted C 1 to C 36 alkyl group, an aromatic group, an isocyanurate moiety, biuret moiety, allophonate moiety, glycoluril moiety, benzoguanamine moiety, polyetheramine moiety, and/or polymeric moiety different from a polyetheramine having an Mn of 500 or greater; wherein each R1 is independently a hydrogen, an alkyl having at least 1 carbon, or a hydroxy functional alkyl having 2 or more carbons; and n is 2-6; and
(b) a film-forming resin reactive with the hydroxy functional alkyl polyurea.
22 . The thermoset composition of claim 21 , wherein the film-forming resin comprises an acid functional resin.
23 . The thermoset composition of claim 21 , wherein the film-forming resin comprises an acid functional acrylic resin, an acid functional polyester resin, and/or an acid functional polyolefin resin.
24 . The thermoset composition of claim 21 , wherein the thermoset composition comprises from 10 to 99 weight percent of the film forming resin and from 0.5 to 50 weight percent of the hydroxy functional alkyl polyurea.
25 . The thermoset composition of claim 21 , wherein R 2 does not comprise a polymeric moiety, wherein a number average molecular weight (Mn) of the hydroxy functional alkyl polyurea is from 100 to 10,000.
26 . The thermoset composition of claim 21 , wherein R 2 comprises a polymeric moiety, wherein a number average molecular weight (Mn) of the hydroxy functional alkyl polyurea is greater than 500.
27 . The thermoset composition of claim 21 , further comprising a catalyst to catalyze a reaction between a hydroxyl group and an acid or isocyanate group in the thermoset composition.
28 . The thermoset composition of claim 21 , further comprising organic solvent and/or water.
29 . The thermoset composition of claim 21 , wherein the thermoset composition is a powder composition.
30 . The thermoset composition of claim 21 , wherein R 2 comprises a substituted or unsubstituted C 1 to C 36 alkyl group and/or an aromatic group, wherein the alkyl group is derived from an isocyanate and/or the aromatic group is derived from an aromatic ring containing isocyanate.
31 . The thermoset composition of claim 21 , wherein the hydroxy functional alkyl polyurea is prepared by reacting an isocyanate-containing compound with an amino alcohol.
32 . The thermoset composition of claim 21 , wherein the isocyanate-containing compound and the amino alcohol are reacted in an equivalent ratio of amine to isocyanate of from 2:1 to 1:2.
33 . The thermoset composition of claim 21 , wherein the hydroxy functional alkyl polyurea is prepared by reacting an amino alcohol with carbonate to form hydroxyalkyl carbamate, and reacting the hydroxyalkyl carbamate with an amine to form the hydroxy functional alkyl polyurea.
34 . The thermoset composition of claim 21 , wherein the thermoset composition is substantially formaldehyde free.
35 . The thermoset composition of claim 21 , wherein the thermoset composition is substantially free of bisphenol A and epoxy compounds derived from bisphenol A and/or bisphenol F and epoxy compounds derived from bisphenol F.
36 . The thermoset composition of claim 21 , wherein the thermoset composition is formulated as a coating.
37 . The thermoset composition of claim 21 , wherein when R 2 is a substituted or unsubstituted C 1 to C 36 alkyl group, the film-forming resin comprises COOH functionality that reacts with the polyurea to form an ester linkage.
38 . A substrate a least partially coated with the thermoset composition of claim 21 .
39 . The substrate of claim 38 , wherein the substrate comprises a package.
40 . The substrate of claim 38 , wherein the substrate comprises a metal can.
41 . The substrate of claim 38 , wherein the substrate comprises a metal sheet or coil.
42 . The substrate of claim 38 , wherein the substrate comprises wood particles.Join the waitlist — get patent alerts
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