# US 11,078,323 B2 · Silane coupling agents

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- Number: US 11,078,323 B2
- Document ID: US11078323B2
- Status: Granted
- Kind: B2
- Application number: 16/656,693
- Filed: 2019-10-18
- Published: 2020-02-13
- Granted: 2021-08-03
- Earliest claimed: 2017-04-25
- Assignees: Henkel AG & Co. KGaA
- Applicants: Henkel AG & Co. KGaA
- Inventors: Rok Brisar; Udo Kragl; Jan-Erik Damke; Johann Klein; Esteban Mejia
- Web page: https://patentgrep.com/patent/US11078323B2

## CPC

- C08G 18/837: {by silicon containing compounds}
- C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G 18/48: Polyethers
- C08G 18/4825: {Polyethers containing two hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)}
- C08G 18/72: Polyisocyanates or polyisothiocyanates
- C08G 18/755: {and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate}
- C09D 175/08: from polyethers
- C09J 175/08: from polyethers
- C07F 7/081: {comprising at least one atom selected from the elements N, O, halogen, S, Se or Te}
- C07F 7/18: Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C08G 2190/00: Compositions for sealing or packing joints
- 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)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

The present invention discloses silylated polyurethanes obtainable by reacting at least one polyols, at least one polyisocyanates, at least one amide-functionalized silanes of the general formula (I) as described herein and their preparation methods, curable compositions comprising the silylated polyurethanes and their use as adhesive, sealant, spray foam and/or coating.

## Claims

### Claim 1

A silylated polyurethane that is the reaction product of a mixture comprising:
a) at least one polyol having a number average molecular weight of from 1000 to 50,000 g/mol;
b) at least one polyisocyanate, diisocyanate; and
c) at least one amide-functionalized silane of the general formula (I)
wherein
R1 is hydrogen; R2 and R3 are same or different and are, independently from one another, selected from the group consisting of hydrogen and substituted or unsubstituted hydrocarbon residues, alkyl or aryl residues, more alkyl residues, having 1 to 20 carbon atoms, 1 to 8 carbon atoms, most methyl, ethyl, or n-propyl residue; R4 is selected from linear or branched, substituted or unsubstituted hydrocarbon residues, alkyl residues, having 1 to 20 carbon atoms, 1 to 8 carbon atoms, more ethyl, n-propyl or n-butyl residue; R6 is selected from the group consisting of hydrogen and linear or branched, substituted or unsubstituted hydrocarbon residues, alkyl or aryl residues, having 1 to 20 carbon atoms, 1 to 8 carbon atoms, more methyl, ethyl or n-propyl residue; and
n is 0, 1, 2 or 3, 3.

### Claim 2 (depends on 1)

The silylated polyurethane according to claim 1, wherein the amide-functionalized silane of the general formula (I) is the reaction product of at least one aminosilane having a primary amino group with at least one compound having the general formula (II)
wherein R5 is a hydrolysable group selected from the group consisting of a hydroxyl group, alkoxy or aryloxy residues having 1 to 20 carbon atoms, alkoxy residues having 1 to 8 carbon atoms, which can be interrupted by at least one heteroatom selected from N, O, and/or S, alkoxide, triflate, tosylate, and halogens; and R6 is selected from the group consisting of hydrogen and linear or branched, substituted or unsubstituted hydrocarbon residues, alkyl or aryl residues, having 1 to 20 carbon atoms.

### Claim 3 (depends on 2)

The silylated polyurethane according to claim 2, wherein the aminosilane having a primary amino group has the general formula (III)
wherein R1, R2, R3, R4 and n are the same as defined above.

### Claim 4 (depends on 1)

The silylated polyurethane according to claim 1, wherein the at least one polyol comprises a polyether polyol.

### Claim 5 (depends on 1)

The silylated polyurethane according to claim 1, wherein n in the general formulae (I) is 3.

### Claim 6 (depends on 1)

The silylated polyurethane according to claim 1, wherein R3 is selected from alkyl residues having 1 to 8 carbon atoms, methyl, ethyl or n-propyl.

### Claim 7 (depends on 1)

The silylated polyurethane according to claim 1, wherein the silylated polyurethane is obtained by
(a) reacting at least one polyol having a number average molecular weight of from 1000 to 50,000 g/mol with at least one polyisocyanate, diisocyanate, with a stoichiometric excess of the NCO group of the polyisocyanate(s) with respect to the OH group of the polyol(s) to form a NCO-terminated polyurethane prepolymer; and
(b) reacting said NCO-terminated polyurethane prepolymer with at least one amide-functionalized silane of the general formula (I)
wherein R1, R2, R3, R4, R6 and n are the same as defined above.

### Claim 8 (depends on 7)

The silylated polyurethane according to claim 7, wherein a molar ratio of the NCO group of the polyisocyanate(s) to the OH group of the polyol(s) is from 1.01 to 2.0.

### Claim 9 (depends on 1)

The silylated polyurethane according to claim 1, wherein the silylated polyurethane is obtained by
(a) reacting at least one polyisocyanate, with at least one amide-functionalized silane of the general formula (I)
wherein R1, R2, R3, R4, R6 and n are the same as defined above, with a stoichiometric excess of the NCO group of the polyisocyanate(s) with respect to the amino group of the silane(s) of the general formula (I); and
(b) reacting the reaction product obtained in step (a) with at least one polyol having a number average molecular weight of from 1000 to 50,000 g/mol.

### Claim 10 (depends on 9)

The silylated polyurethane according to claim 9, wherein a molar ratio of the NCO group of the polyisocyanate(s) to the amino group of the amide-functionalized silane(s) of the general formula (I) is from 1.1 to 3.0.

### Claim 11

A method for preparing a silylated polyurethane comprising reacting a mixture including:
a) at least one polyol having a number average molecular weight of from 1000 to 50,000 g/mol;
b) at least one polyisocyanate, diisocyanate; and
c) at least one amide-functionalized silane of the general formula (I)
wherein
R1 is hydrogen; R2 and R3 are same or different and are, independently from one another, selected from the group consisting of hydrogen and substituted or unsubstituted hydrocarbon residues, alkyl or aryl residues, more alkyl residues, having 1 to 20 carbon atoms, 1 to 8 carbon atoms, most methyl, ethyl, or n-propyl residue; R4 is selected from linear or branched, substituted or unsubstituted hydrocarbon residues, alkyl residues, having 1 to 20 carbon atoms, 1 to 8 carbon atoms, more ethyl, n-propyl or n-butyl residue; R6 is selected from the group consisting of hydrogen and linear or branched, substituted or unsubstituted hydrocarbon residues, alkyl or aryl residues, having 1 to 20 carbon atoms, 1 to 8 carbon atoms, more methyl, ethyl or n-propyl residue; and
n is 0, 1, 2 or 3, 3.

### Claim 12 (depends on 1)

A curable composition comprising the silylated polyurethane according to claim 1.

### Claim 13 (depends on 12)

The curable composition according to claim 12, further comprising at least one component selected from plasticizer, stabilizer, antioxidant, filler, reactive diluent, drying agent, adhesion promoter, UV stabilizer, rheological agent, solvent and mixtures thereof.

### Claim 14 (depends on 12)

An adhesive, sealant, spray foam and/or coating comprising the curable composition according to claim 12.