Curable compositions containing 1,1-di-activated vinyl compounds that cure by pericyclic reaction mechanisms

Patent metadata

Field	Value
Publication number	US-10934411-B2
Application number	US-201715722443-A
Country	US
Kind code	B2
Filing date	Oct 2, 2017
Priority date	Sep 30, 2016
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

Abstract

Curable compositions containing a compound comprising a conjugated diene group and a 1,1-di-activated vinyl compound are described. The curable compositions can cure by pericyclic reaction mechanisms.

First claim

What is claimed is:

1. A curable composition comprising:
a compound comprising a conjugated diene group; and
a 1,1-di-activated vinyl compound, wherein the 1,1, di-activated vinyl compound comprises a diaryl methylene malonate, a multifunctional form of a dialkyl methylene malonate, a multifunctional form of a diaryl methylene malonate, or a combination thereof.

2. The curable composition of claim 1 , wherein the 1,1-di-activated vinyl compound comprises:
a multifunctional form of a dialkyl methylene malonate; or
a multifunctional form of a diaryl methylene malonate; or
a combination of any thereof.

3. The curable composition of claim 2 , wherein the 1,1-di-activated vinyl compound comprises:
a multifunctional form of diethyl methylene malonate comprising a transesterification adduct of diethyl methylene malonate and at least one polyol.

4. The curable composition of claim 3 , wherein the transesterification adduct of diethyl methylene malonate and at least one polyol comprises a transesterification adduct of diethyl methylene malonate and a diol.

5. The curable composition of claim 4 , wherein the diol comprises an alkane diol.

6. The curable composition of claim 5 , wherein the alkane diol comprises 1,5-pentane diol and/or 1,6-hexanediol.

7. The curable composition of claim 1 , wherein the compound comprising a conjugated diene groups comprises a polymer resin comprising pendant and/or terminal conjugated diene groups.

8. The curable composition of claim 7 , wherein the resin comprises pendant and/or terminal open-chain conjugated diene groups.

9. The curable composition of claim 7 , wherein the resin comprises pendant and/or terminal cyclic conjugated diene groups.

10. The curable composition of claim 9 , wherein the resin comprises pendant and/or terminal cyclopentadiene groups.

11. The curable composition of claim 9 , wherein the resin comprises pendant and/or terminal thiophene groups.

12. The curable composition of claim 9 , wherein the resin comprises pendant and/or terminal pyrrole groups.

13. The curable composition of claim 9 , wherein the resin comprises pendant and/or terminal furan groups.

14. The curable composition of claim 7 , wherein the resin comprises a reaction product of a polyisocyanate and a conjugated diene compound comprising an active hydrogen group.

15. The curable composition of claim 7 , wherein the resin comprises a reaction product of a polyol, polyamine, or polythiol and a conjugated diene compound comprising an isocyanate group.

16. The curable composition of claim 7 , wherein the resin comprises a polyurethane resin, a polyurea resin, an acrylic resin, a polyester resin, a polycarbonate resin, a polysiloxane resin, an epoxy resin, a melamine resin, or a phenol formaldehyde resin, or a composite resin comprising a polymer comprising two or more backbone functionalities, or a combination of any thereof.

17. A coating composition comprising the curable composition of claim 1 .

18. An adhesive or sealant composition comprising the curable composition of claim 1 .

19. A process for applying a curable composition to a substrate comprising:
applying the curable composition of claim 1 to at least a portion of a substrate; and
curing the curable composition;
wherein the curing comprises a crosslinking reaction between (1) the compound comprising a conjugated diene group and (2) the 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof.

20. The process of claim 19 , wherein the crosslinking reaction comprises a pericyclic reaction.

21. The process of claim 19 , wherein the crosslinking reaction comprises a cycloaddition reaction.

22. The process of claim 19 , wherein the crosslinking reaction comprises a Diels-Alder reaction.

23. The process of claim 19 , wherein the crosslinking reaction comprises a pericyclic reaction that occurs in a cascade with another chemical transformation.

24. A coating, adhesive, or sealant system comprising:
a coating, adhesive, or sealant layer applied to at least a portion of a substrate, wherein the coating, adhesive, or sealant layer comprises a Diels-Alder addition reaction product of:
a resin comprising pendant and/or terminal conjugated diene groups; and
a 1,1-di-activated vinyl compound, wherein the 1,1, di-activated vinyl compound comprises a diaryl methylene malonate, a multifunctional form of a dialkyl methylene malonate, a multifunctional form of a diaryl methylene malonate, or a combination thereof.

25. The coating, adhesive, or sealant system of claim 24 , wherein the 1,1-di-activated vinyl compound comprises a multifunctional form of a dialkyl methylene malonate, a multifunctional form of a diaryl methylene malonate, or a combination thereof.

26. The coating, adhesive, or sealant system of claim 25 , wherein the 1,1-di-activated vinyl compound comprises:
a multifunctional form of diethyl methylene malonate comprising a transesterification adduct of diethyl methylene malonate and at least one polyol.

27. The coating, adhesive, or sealant system of claim 26 , wherein the transesterification adduct of diethyl methylene malonate and at least one polyol comprises a transesterification adduct of diethyl methylene malonate and a diol.

28. The coating, adhesive, or sealant system of claim 27 , wherein the diol comprises 1,5-pentane diol and/or 1,6-hexanediol.

29. The coating, adhesive, or sealant system of claim 24 , wherein the resin comprises pendant and/or terminal open-chain conjugated diene groups.

30. The coating, adhesive, or sealant system of claim 24 , wherein the resin comprises pendant and/or terminal cyclic conjugated diene groups.

31. The coating, adhesive, or sealant system of claim 24 , wherein the resin comprises pendant and/or terminal cyclopentadiene groups, thiophene groups, pyrrole groups, or furan groups, or combinations of any thereof.

32. The coating, adhesive, or sealant system of claim 24 , wherein the resin comprises a reaction product of a polyisocyanate and a conjugated diene compound comprising an active hydrogen group.

33. The coating, adhesive, or sealant system of claim 24 , wherein the resin comprises a reaction product of a polyol, polyamine, or polythiol and a conjugated diene compound comprising an isocyanate group.

34. The coating, adhesive, or sealant system of claim 24 , wherein the resin comprises a polyurethane resin, a polyurea resin, an acrylic resin, a polyester resin, a polycarbonate resin, a polysiloxane resin, an epoxy resin, a melamine resin, or a phenol formaldehyde resin, or a composite resin comprising a polymer comprising two or more backbone functionalities, or a combination of any thereof.

35. The coating, adhesive, or sealant system of claim 24 , wherein the coating, adhesive, or sealant layer exhibits intumescence, delamination, or self-healing properties upon application of heat, radiation, pressure, and/or a catalyst composition.

36. An article comprising the coating, adhesive, or sealant system of claim 24 deposited on a surface of the article.

37. The article of claim 36 , wherein the article comprises a vehicle component, an architectural component, or a component of a free-standing structure.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Martz Jonathan Thomas
• Zalich Michael Andrew
• Gottumukkala Aditya Lakshmi Narasimha Raju
• Hellring Stuart Damon
• Peskens Ronnie Albertus Johannes

Classifications

• C08K5/09 Primary

  Carboxylic acids; Metal salts thereof; Anhydrides thereof · CPC title

• G01N24/088

  Assessment or manipulation of a chemical or biochemical reaction, e.g. verification whether a chemical reaction occurred or whether a ligand binds to a receptor in drug screening or assessing reaction kinetics · CPC title

• C09J11/06

  organic · CPC title

• G01R33/46

  NMR spectroscopy · CPC title

• C08K5/053

  Polyhydroxylic alcohols · CPC title