Alternative crosslinking mechanisms for polyurethane-based systems

Patent metadata

Field	Value
Publication number	US-11427673-B2
Application number	US-201916269606-A
Country	US
Kind code	B2
Filing date	Feb 7, 2019
Priority date	Feb 7, 2019
Publication date	Aug 30, 2022
Grant date	Aug 30, 2022

Abstract

The present invention provides compositions comprising the reaction product of an aliphatic diisocyanate, and a reactive intermediate made from one selected from the group consisting of oxazolidinones, benzoic sulfimides (saccharins), 1H-indole-2,3-diones (isatins), succinamides, N-hydroxysuccinamides, 4-hydroxy-3-methoxybenzaldehydes (vanillins), α-ketoamides, piperazines, benzofuranones, 3,4-dihydroxycyclobut-3-ene-1,2-diones (squaric acids), squaric acid esters, α-ketoamides, anilines, and α-ketoamide, phenols. The aliphatic diisocyanate comprises one selected from the group consisting of isocyanurates, biurets, iminooxadiazine diones, urethanes, uretdiones, carbodiimides, and allophanates. The resulting compositions may be useful in producing coatings, adhesives, sealants, castings, composites and films having durability, color stability, high gloss, and chemical resistance properties similar to those made from polyurethane.

First claim

What is claimed is:

1. A composition comprising the reaction product of
a. at least one of a prepolymer, oligomer or monomer selected from the group consisting of aliphatic diisocyanates, isocyanurates, biurets, iminooxadiazine diones, urethanes, uretdiones, carbodiimides, and allophanates; and
b. a reactive intermediate made from a-ketoamides and piperazines, α-ketoamides and anilines, or α-ketoamides and phenols.

2. The composition according to claim 1 , wherein the prepolymer, oligomer or monomer has 4 to 30 carbon atoms.

3. The composition according to claim 1 , wherein the prepolymer, oligomer or monomer is selected from the group consisting of tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate (HDI), 2,2,4- (or 2,4,4-) trimethyl-1,6-hexamethylene diisocyanate, pentamethylene diisocyanate (PDI), isophorone diisocyanate (IPDI), lysine diisocyanate, hydrogenated xylene diisocyanate, hydrogenated diphenylmethane diisocyanate, 1,4-diisocyanatocyclohexane, 1,3-bis(diisocyanatomethyl)cyclohexane, and 4,4′-dicyclohexylmethane diisocyanate.

4. The composition according to claim 1 , wherein the prepolymer, oligomer or monomer comprises one selected from the group consisting of isocyanurates, biurets, and iminooxadiazine diones.

5. The composition according to claim 1 , wherein the prepolymer, oligomer or monomer comprises 1,6-hexamethylene diisocyanate (HDI) trimer.

6. A composition comprising a reaction product is-selected from the group consisting of N-[6-[3,5-bis[6-[[4-(2-ethoxy-3,4-dioxo-cyclobuten-1-yl)piperazine-1-carbonyl]amino]hexyl]-2,4,6-trioxo-1,3,5-triazinan-1-yl]hexyl]-4-(2-ethoxy-3,4-dioxo-cyclobuten-1-yl)piperazine-1-carboxamide, 4-[[(2-ethoxy-3,4-dioxo-cyclobuten-1-yl)amino]methyl]phenyl]N-[6-[3,5-bis[6-[[4-[[(2-ethoxy-3,4-dioxo-cyclobuten-1-yl)amino]methyl]phenoxy]carbonylamino]hexyl]-2,4,6-trioxo-1,3,5-triazinan-1-yl]hexyl]carbamate, 4-[2-[(2-oxo-2-phenyl-acetyl)amino]ethyl]-N-6-[2,4,6-trioxo-3,5-bis[6-[[4-[2-[(2-oxo-2-phenyl-acetyl)amino]ethyl]piperazine-1-carbonyl]amino]hexyl]-1,3,5-triazinan-1-yl]hexyl]piperazine-1-carboxamide, [4-[[(2-oxo-2-phenyl-acetyl)amino]methyl]phenyl]N-[6-[2,4,6-trioxo-3,5-bis[6-[[4-[[(2-oxo-2-phenyl-acetyl)amino]methyl]phenoxy]carbonylamino]hexyl]-1,3,5-triazinan-1-yl]hexyl]carbamate, 2-oxo-2-phenyl-N-[[4-[6-[2,4,6-trioxo-3,5-bis[6-[[4-[[(2-oxo-2-phenyl-acetyl)amino]methyl]phenyl]carbamoylamino]hexyl]-1,3,5-triazinan-1-yl]hexylcarbamoylamino]phenyl]methyl]acetamide, 2-[(2-oxo-2-phenyl-acetyl)amino]ethyl N-[6-[2,4,6-trioxo-3,5-bis[6-[2-[(2-oxo-2-phenyl-acetyl)amino]ethoxycarbonyl amino]hexyl]-1,3,5-triazinan-1-yl]hexyl]carbamate, and (4-formyl-2-methoxy-phenyl) N-[6-[3,5-bis[6-[(4-formyl-2-methoxy-phenoxy)carbonylamino]hexyl]-2,4,6-trioxo-1,3,5-triazinan-1-yl]hexyl]carbamate.

7. A curable composition comprising the reaction product of the composition according to claim 1 and a nucleophile in the presence of a catalyst.

8. A curable composition comprising the reaction product of the composition according to claim 6 and a nucleophile in the presence of a catalyst.

9. The curable composition according to claim 7 , wherein the nucleophile is selected from the group consisting of an amine and a polyol.

10. The curable composition according to claim 9 , wherein the amine is an aspartic ester functional amine.

11. The curable composition according to claim 9 , wherein the amine is a polyoxypropylene triamine.

12. The curable composition according to claim 9 , wherein the polyol is a hydroxy-functional acrylic polyol.

13. The curable composition according to claim 7 , wherein the curable composition is selected from the group consisting of a coatings, adhesives, sealants, castings, composites, and films.

14. The curable composition according to claim 7 , wherein the catalyst is selected from the group consisting of dibutyltin dilaurate, p-toluenesulfonic acid, 1,4-diazabicyclo[2.2.2]octane, and zinc neodecanoate.

15. A process of making one of a coating, an adhesive, a casting, a composite, a sealant, and a film, the process comprising reacting the composition according to claim 1 with a nucleophile in the presence of a catalyst.

16. The process according to claim 15 , wherein the nucleophile is selected from the group consisting of an amine and a polyol.

17. The process according to claim 16 , wherein the amine is an aspartic ester functional amine.

18. The process according to claim 16 , wherein the amine is a polyoxypropylene triamine.

19. The process according to claim 16 , wherein the polyol is a hydroxy-functional acrylic polyol.

20. A substrate having applied thereto the curable composition according to claim 7 .

21. A substrate having applied thereto the curable composition according to claim 8 .

Assignees

• Covestro Llc

Inventors

• Warner John
• Baldino Carmen
• Whitfield Justin
• Kearney Frederick Richard

Classifications

• C08G18/73

  acyclic · CPC title

• C08G18/2063

  having two nitrogen atoms in the condensed ring system · CPC title

• C08G18/7831

  containing biuret groups · CPC title

• C08G18/222

  metal compounds not provided for in groups C08G18/225 - C08G18/26 · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title