# US 11,111,341 B2 · Click chemistry for sealants and adhesives

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- Number: US 11,111,341 B2
- Document ID: US11111341B2
- Status: Granted
- Kind: B2
- Application number: 16/669,924
- Filed: 2019-10-31
- Published: 2020-03-05
- Granted: 2021-09-07
- Earliest claimed: 2017-05-11
- Assignees: Chem Link, Inc.
- Applicants: Chem Link, Inc.
- Inventors: Baljinder Kaur; Jonathan Ballema
- Web page: https://patentgrep.com/patent/US11111341B2

## CPC

- C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K)
- C08G 63/91: Polymers modified by chemical after-treatment
- C09D 201/10: containing hydrolysable silane groups
- C09J 183/00: Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J 183/04: Polysiloxanes
- C09J 183/10: Block or graft copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C09J151/08, C09J153/00)
- C09J 185/00: Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon; Adhesives based on derivatives of such polymers
- C09J 201/10: containing hydrolysable silane groups
- C09K 3/1018: {Macromolecular compounds having one or more carbon-to-silicon linkages}
- C08G 77/12: containing silicon bound to hydrogen
- C08G 77/20: containing silicon bound to unsaturated aliphatic groups
- C08J 2333/06: of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C08J 2333/12: Homopolymers or copolymers of methyl methacrylate
- C08J 2347/00: Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Derivatives of such polymers (C08J2345/00 takes precedence; of conjugated diene rubbers C08J2309/00 - C08J2321/00)
- C08J 2367/00: Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J 2371/00: Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
- C08J 2381/04: Polysulfides
- C08J 2383/04: Polysiloxanes
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The invention described herein generally pertains to a composition that includes a silyl-terminated polymer having silyl groups linked to a polymer backbone via triazole. The silyl-terminated polymer is a reaction product of a functionalized polymer backbone and a functionalized silane. The polymer backbone includes a first functional group, which may be one of an azide or an alkyne. The functionalized silane includes a second functional group may also be one of an azide or an alkyne, but is also different from the first functional group. The functionalized polymer backbone is reacted with the functionalized silane in the presence of a metal catalyst.

## Claims

### Claim 1

A method for producing a curable composition, comprising:
reacting a functionalized polymer bearing a first functional group with a functionalized silane bearing a second functional group in the presence of a metal catalyst,
wherein the first functional group is selected from a group consisting of an azide and an alkyne;
wherein the second functional group is different from the first functional group and selected from a group consisting of an azide and an alkyne; and
wherein the result is a silyl-terminated polymer having a first silane group and a second silane group, the first silane group linked to the functionalized polymer via a first triazole moiety, and the second silane group linked to the functionalized polymer via a second triazole moiety;
wherein the metal catalyst promotes cross-linking of the first silane group and the second silane group in the presence of atmospheric moisture.

### Claim 2 (depends on 1)

The method of claim 1, wherein the metal catalyst is copper I.

### Claim 3 (depends on 1)

The method of claim 1, wherein the reacting further comprises:
adding copper II to a system including the functionalized polymer and the functionalized silane.

### Claim 4 (depends on 3)

The method of claim 3, further comprising converting the copper II to copper I to initiate the reaction.

### Claim 5 (depends on 4)

The method of claim 4, wherein converting the copper II comprises exposing the copper II to ultraviolet radiation.

### Claim 6 (depends on 4)

The method of claim 4, wherein converting the copper II comprises adding a reducing agent.

### Claim 7 (depends on 1)

The method of claim 1, wherein the polymer is selected from a group consisting of polyether, polyester, polydimethyl siloxane, polymethyl methacrylate, polyacrylate, polybutadiene, and polysulfide.

### Claim 8 (depends on 1)

The method of claim 1, wherein one of the first or second functional groups is a strained alkyne group capable of reacting with an azide group without a metal catalyst.

### Claim 9 (depends on 1)

The method of claim 1, wherein the functionalized polymer is a hybrid polymer comprising an inorganic polymer linked to an organic polymer.

### Claim 10 (depends on 9)

The method of claim 9, wherein the inorganic polymer and the organic polymer are linked via triazole as a result of a click reaction.
