Curable compositions, products and articles formed therefrom, and methods of forming the same

Patent metadata

Field	Value
Publication number	US-10793667-B2
Application number	US-201916269600-A
Country	US
Kind code	B2
Filing date	Feb 7, 2019
Priority date	Feb 7, 2019
Publication date	Oct 6, 2020
Grant date	Oct 6, 2020

Abstract

A curable composition, a method of making the curable composition, and an article and product produced therefrom are provided. A morpholinedione is contacted with an isocyanate to form a resin composition. The resin composition is reacted with an amine to form the curable composition.

First claim

What is claimed is:

1. A method comprising:
contacting a morpholinedione with an isocyanate to form a resin composition; and
reacting the resin composition with an amine to form a curable composition.

2. The method according to claim 1 , wherein the reacting step comprises cross-linking the resin composition with the amine.

3. The method according to claim 2 , wherein cross-linking further comprises a ring opening reaction.

4. The method according to claim 1 , further comprising curing the curable composition to form an article.

5. The method according to claim 4 , wherein the article is at least one component of at least one of an adhesive, a coating, a casting, a sealant, an elastomer, and a foam.

6. The method according to claim 1 , wherein the amine comprises a primary amine.

7. The method according to claim 1 , wherein the amine comprises at least one of diethylenetriamine, 2-methylpentamethylenediamine, isophrone diamine, 4,4′-diaminodicyclohexylmethane, 3, 3′-dimethyl-4, 4′diaminodicyclohexylmethane, ethylene diamine, ethylene triamine, propylene diamine, tetramethylene diamine, 1,6-hexamethylene diamine, bis(6-aminohexyl)ether, tricyclodecane diamine, N,N′-dimethyldiethyltriamine, cyclohexyl-1,2,4-triamine, cyclohexyl-1,2,4,5-tetraamine, 3,4,5-triaminopyran, 3,4-diaminofuran, cycloaliphatic diamines, triaminononane, polyether amine, and a polyaspartic ester based amine.

8. The method according to claim 1 , wherein the morpholinedione comprises a N-hydroxyethylmorphonline-2, 3-dione.

9. The method according to claim 1 , wherein the isocyanate has a functionality of at least 2.

10. The method according to claim 1 , wherein the isocyanate is selected from the group consisting of 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethyl-1,6-hexamethylene diisocyanate, 1,12-dodecamethylene diisocyanate, cyclohexane-1,3- and 1,4-diisocyanate, 1-isocyanato-2-isocyanato-methyl cyclopentane, 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl cyclohexane (isophorone diisocyanate or IPDI), bis-(4-isocyantocyclohexyl)methane, 1,3- and 1,4-bis(isocyanatomethyl)-cyclohexane, bis-(4-isocyanato-3-methyl-cyclohexyl)-methane, α,α,α′,α′-tetramethyl-1,3- and 1,4-xylene diisocyanate, 1-isocyanato-1-methyl-4(3)-isocyanato-methyl cyclohexane, and 2,4- and 2,6-hexahydro-toluene diisocyanate, toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), PDI (pentane diisocyanate—bio-based), 2-methylpentamethylene 1,5-diisocyanate, lysine and lysine ester diisocyanate, 1,4-diisocyanato-2,2,6-trimethylcyclohexane (TMCDI), 1,3- and 1,4-bis(isocyanatomethyl)cyclohexane), m- and p-tetramethyl-1,3-xylylene diisocyanate, m- and p-tetramethyl-1,4-xylylene diisocyanate, bis(1-isocyanato-1-methylethyl)naphthalene, 1,3- and 1,4-phenylene diisocyanate, 2,3,5,6-tetramethyl-1,4-diisocyanatobenzene, naphthalene 1,5-diisocyanate (NID), 3,3′-dimethyl-4,4′-diisocyanatobiphenyl (TOBI); oligomers, polymers, isomers thereof, and combinations thereof.

11. The method according to claim 1 , wherein the isocyanate comprises at least one of a polyurethane resin, a polyurea resin, an acrylic resin, a polyester resin, a polycarbonate resin, a polysiloxane resin, an epoxy resin, a melamine resin, and a phenol formaldehyde resin.

12. The method according to claim 1 , wherein the curable composition has a free hydroxyl group.

13. The method according to claim 1 , further comprising contacting the curable composition with a second isocyanate to form a secondary curable composition, wherein the second isocyanate is different than or the same as the first isocyanate.

14. An article produced by the process, comprising:
contacting a morpholinedione with an isocyanate to form a resin composition; and
reacting the resin composition with an amine to form a curable composition.

15. The article according to claim 14 , wherein the morpholinedione comprises a N-hydroxyethylmorpholine-2, 3-dione.

16. The article according to claim 14 , wherein the curable composition has a free hydroxyl group.

17. The article according to claim 14 , further comprising contacting the curable composition with a second isocyanate to form a secondary curable composition.

18. The article according to claim 17 , wherein the second isocyanate is different than the first isocyanate.

19. The article according to claim 17 , wherein the second isocyanate is the same as the first isocyanate.

20. The article according to claim 14 , wherein the curable composition has a microhardness of at least 2 N/mm 2 according to DIN EN ISO 14577-1:2015.

21. The article according to claim 14 , wherein the curable composition has a methyl ethyl ketone rub resistance of at least 100 double rubs according to ASTM D4752-10(2015).

22. The article according to claim 14 , wherein the curable composition has a cross-hatch adhesion of at least 4B according to ASTM D 3359-17.

23. The article according to claim 14 , wherein the article is at least one component of at least one of a coating, an adhesive, a casting, a sealant, an elastomer, and a foam.

24. A curable composition comprising the following structure:

wherein
R 1 is an alkyl bridging group,
two of R 2 , R 3 , and R 5 are a carbonyl group and the remaining one of R 2 , R 3 , and R 5 is a methylene bridge,
R 6 is an alkyl group or an aryl group,
R 7 is an alkyl group or an aryl group, and
Y is at least one of a hydrogen atom, an alkyl group, an aryl group, and a carbamate group.

25. The curable composition according to claim 24 , wherein Y comprises a carbamate group and one of an alkyl group and an aryl group.

26. The curable composition according to claim 25 , wherein R 6 comprises a different alkyl group or aryl group than Y.

27. The curable composition according to claim 24 , wherein Y is a hydrogen atom.

28. The curable composition of claim 24 , wherein the composition is at least one component of at least one of a coating, an adhesive, a casting, a sealant, an elastomer, and a foam.

29. A product that is formed by the curable composition according to claim 24 .

Assignees

• Covestro Deutschland Ag
• Covestro Llc

Inventors

• Pochorovski Igor
• Ekin Alan

Classifications

• C09J175/04

  Polyurethanes · CPC title

• C09D175/12 Primary

  from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group · CPC title

• C08G18/807

  with nitrogen containing compounds · CPC title

• C07D265/32

  with oxygen atoms directly attached to ring carbon atoms · CPC title

• C08G18/2875

  Monohydroxy compounds containing tertiary amino groups · CPC title