Synthesis of polyurethane polymers via copper azide-alkyne click chemistry for coatings, adhesives, sealants and elastomer applications

Patent metadata

Field	Value
Publication number	US-9790398-B2
Application number	US-201414766342-A
Country	US
Kind code	B2
Filing date	Feb 5, 2014
Priority date	Feb 8, 2013
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

Abstract

The present application is directed at the reaction product of an azide compound having two or more azide groups attached thereto and an alkyne compound having two or more alkyne groups attached thereto, wherein the azide and alkyne groups react in a 1,3-dipolar cyclo addition to form 1,4-disubstituted triazols and wherein the azide or alkyne compound or both include —O—(C═O)—NR— functional groups. The reaction products can be used as coatings, such as for flat roofs, sealants, adhesives and in elastomer applications. Methods for producing the reaction products as well as substrates including a coating of the reaction product are also disclosed.

First claim

The invention claimed is:

1. A substrate comprising:
a coating of a reaction product of:
an azide compound having 2 or more azide groups attached thereto; and
an alkyne compound having 2 or more alkyne groups attached thereto, wherein the azide and alkyne groups react in a 1,3 dipolar cycloaddition to form 1,4-disubstituted triazoles and wherein the azide or alkyne compound or both include —O—(C═O)—NR— groups with R=hydrogen or alkyl,
wherein the substrate is part of a roof structure.

2. The substrate of claim 1 ,
wherein the azide compound and/or the alkyne compound comprises:
a prepolymer having an azide group or an alkyne group attached thereto.

3. The substrate of claim 2 , wherein the prepolymer is a polyurethane prepolymer.

4. The substrate of claim 1 ,
wherein the azide compound has a hydroxyl group on the β-carbon of the azide group.

5. The substrate of claim 1 , wherein the azide compound is formed as a reaction of a nucleophilic azide with an epoxy compound and subsequent reaction with a polyisocyanate.

6. The substrate of claim 4 , wherein the azide compound is formed as a reaction of a polyisocyanate or isocyanate terminated polyurethane prepolymer and an epoxy compound having a functional group reactive towards isocyanates, and subsequent reaction with a nucleophilic azide.

7. The substrate of claim 6 , wherein the epoxy compound is glycidol.

8. The substrate of claim 6 , wherein the polyisocyanate is MDI or a prepolymer containing terminal MDI residues.

9. The substrate of claim 6 , wherein the functional group is a hydroxyl group.

10. The substrate of claim 1 , wherein the alkyne compound is formed as a reaction of a polyisocyanate and an alkyne having a functional group reactive towards isocyanates.

11. The substrate of claim 10 , wherein the functional group is an amine, hydroxyl or thiol group.

12. The substrate of claim 1 , wherein the alkyne compound is formed as a reaction of an epoxy compound and an alkyne having a functional group reactive towards epoxides, and subsequent reaction with an alkyne group-containing alkylation agent.

13. The substrate of claim 12 , wherein the alkyne group-containing alkylation agent is a propargyl halogenide.

14. The substrate of claim 12 , wherein the functional group is an amine or a thiol group.

15. The substrate according to claim 1 , wherein the reaction product is configured as a coating, a sealant, an adhesive or an elastomer.

Assignees

• Sika Tech Ag

Inventors

• Carter Neil
• Martin Ian
• Coward Alexander
• Gatrell Mark
• Byrne Michael
• Cullen John E
• Cormack Peter

Classifications

• C09J175/04

  Polyurethanes · CPC title

• C09D163/10

  Epoxy resins modified by unsaturated compounds · CPC title

• C09D175/08

  from polyethers · CPC title

• C09J175/08

  from polyethers · CPC title

• C08G18/7671

  containing only one alkylene bisphenyl group · CPC title