Curable Polyisocyanate Composition Comprising an Epoxy

• US 20150065611A1
• Filed: 11/07/2012
• Published: 03/05/2015
• Est. Priority Date: 11/22/2011
• Status: Active Grant

• Current Assignee: Huntsman International LLC (Huntsman Corporation)
• Original Assignee: Huntsman International LLC (Huntsman Corporation)
• Inventors: Esbelin, Christian, Verbeke, Hans Godelieve Guido, Verbeke, Hugo
• Granted Patent: US 9,926,447 B2
• Time in Patent Office: Days
• US Class Current: 523/455
• CPC Class Codes: C08G 59/066 with chain extension or advancing agents
• CPC Class Codes: C08G 59/4021 Ureas; Thioureas; Guanidines; Dicyandiamides
• CPC Class Codes: C08G 59/44 Amides
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C08L 75/04 Polyurethanes

Abstract

Curable composition obtained by combining and mixing an epoxy resin composition, comprising an epoxy resin and a carboxamide, and a polyisocyanate composition, comprising a polyisocyanate, a lithium halide and a urea compound, wherein the number of moles of lithium halide per isocyanate equivalent ranges of from 0.0001-0.04 and the number of urea+biuret equivalents per isocyanate equivalent of from 0.0001-0.4.

Claims

1. A curable composition obtained by combining and mixing

a polyisocyanate composition, comprising a polyisocyanate, a lithium halide and a urea compound that is the reaction product of a second polyisocyanate and an amine, and wherein the urea compound has an average molecular weight of 500-15000 and optionally comprising biuret groups wherein the number of moles of lithium halide per isocyanate equivalent ranges of from 0.0001-0.04 and the number of urea 1 biuret equivalents per isocyanate equivalent ranges of from 0.0001-0.4 and the number of epoxy equivalents per isocyanate equivalent ranges of from 0.003-1, and wherein the polyisocyanate and the second polyisocyanate may be the same or different, and

an epoxy resin, composition comprising an epoxy resin, a compound which comprises a carboxamide group having the structure —

CO—

NH₂ and optionally a solvent which has no isocyanate-reactive groups, and, optionally, wherein the number of carboxamide equivalents per epoxy equivalent is 0.0005-1.

2. The composition according to claim 1, wherein the compound which comprises a carboxamide group has the structure NH₂—

CO—

R wherein R is

     1) hydrogen (—

H),

     2) —

NR₁R₂,

     3) hydrocarbyl having 1-20 carbon atoms and optionally comprising hydroxy, ether, halogen and/or amine groups, or

     4) —

R₃—

CO—

NH₂, wherein R₁ and R₂, independently from each other, are selected from hydrogen, hydroxy, halogen and hydrocarbyl groups which hydrocarbyl groups have 1-10 carbon atoms and optionally comprise hydroxy, ether, halogen and/or amine groups and wherein R₃ is a bivalent hydrocarbon radical having up to 8 carbon atoms and mixtures of such compounds and wherein the number of carboxamide equivalents per epoxy equivalent is 0.01-0.5.

3. The composition according to claim 1, wherein the compound which comprises a carboxamide group has the structure NH₂—

CO—

R wherein R is

     1) —

NR₁R₂,

     2) alkyl having 1-10 carbon atoms and optionally comprising 1-3 hydroxy and/or ether groups,

     3) phenyl or

     4) tolyl, wherein R₁ and R₂, independently from each other, are selected from hydrogen, hydroxy, phenyl, tolyl and alkyl having 1-6 carbon atoms and optionally comprising an hydroxy and/or an ether group and mixtures of such compounds.

4. The composition according to claim 1, wherein the epoxy resin composition further comprises a monool and/or a polyol and wherein the number of hydroxy equivalents per epoxy equivalent is at most 0.019.

5. The composition according to claim 1, wherein the urea compound does not comprise other isocyanate-reactive groups than urea groups and wherein the number of urea+biuret equivalents per isocyanate equivalent is 0.001-0.2 and wherein the urea compound has been prepared by reacting a methylene diphenyl diisocyanate or a polyisocyanate comprising a methylene diphenyl diisocyanate or a mixture of these polyisocyanates with a polyoxyalkylene monoamine comprising oxypropylene groups in an amount of at least 50% by weight calculated on the total weight of the monoamine molecule and having an average molecular weight of 200-3000 and wherein the amine is a primary amine and wherein the number of urea+biuret equivalents per mole of lithium halide is 0.5-60.

6. The composition according to any of claim 1, wherein the polyisocyanate is a methylene diphenyl diisocyanate or a polyisocyanate composition comprising methylene diphenyl diisocyanate or a mixture of such polyisocyanates.

7. The composition according to any of claim 1, wherein the amount of lithium halide is 0.00015-0.025 moles per isocyanate equivalent.

8. The composition according to any of claim 1, wherein the lithium halide is lithium chloride.

9. The composition according to claim 1, wherein the epoxy resin is liquid at 20°

C.

10. A process for making a curable composition according to any of claim 1, by combining and mixing the polyisocyanate composition and the epoxy resin composition, wherein the epoxy resin composition is used in an amount such that the number of epoxy equivalents per isocyanate equivalent ranges from 0.003-1.

11. The process according to any of claim 10, further comprising reacting the curable composition at an elevated temperature.

14. The curable composition according to claim 1, wherein the number of carboxamide equivalents per epoxy equivalent is 0.005-0.7.

15. The curable composition according to claim 1, wherein the number of carboxamide equivalents per epoxy equivalent is 0.01-0.5.

16. The curable composition according to claim 4, herein the number of hydroxy equivalents per epoxy equivalent is at most 0.014.

17. The curable composition according to claim 4, wherein the number of hydroxyl equivalents per epoxy equivalent is at most 0.010.

12-13. -13. (canceled)