# US 10,118,984 B2 · Silylated polyurethanes, their preparation and use

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,118,984 B2
- Document ID: US10118984B2
- Status: Granted
- Kind: B2
- Application number: 15/697,499
- Filed: 2017-09-07
- Published: 2017-12-21
- Granted: 2018-11-06
- Earliest claimed: 2015-03-11
- Assignees: Henkel AG & Co. KGaA
- Applicants: Henkel AG & Co. KGaA
- Inventors: Ralf Bätzgen; Jan-Erik Damke; David Briers; Johann Klein
- Web page: https://patentgrep.com/patent/US10118984B2

## CPC

- C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G 18/227: {of antimony, bismuth or arsenic}
- C08G 18/4825: {Polyethers containing two hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)}
- C08G 18/718: {containing silicon}
- C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

A silylated polyurethane obtainable by a process comprising the following steps: (a) reacting at least one polyol with at least one triisocyanate to form a hydroxyl-terminated polyurethane prepolymer, and (b) reacting said polyurethane prepolymer with at least one isocyanatosilane of the formula (1): OCN—R—Si—(X)m(R1)3−m, wherein m is 0, 1 or 2, each R1 is independently from each other a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, or —OCH(R2)COOR3, wherein R2 is hydrogen or an alkyl group having 1 to 4 carbon atoms and R3 is a straight-chain or branched alkyl group having 1 to 8 carbon atoms, each X is independently from each other and optionally substituted hydrocarbon group having 1 to 10 carbon atoms, which can be interrupted by at least one heteroatom, and R is a difunctional organic group, to endcap the hydroxyl groups on said prepolymer with said isocyanatosilane. The silylated polyurethanes are suitable for use in a preparation as an adhesive, sealant, or coating agent.

## Claims

### Claim 1

A silylated polyurethane having a viscosity of about 41,200 mPas to about 78,600 mPas and obtained by a process comprising the following steps:
(a) reacting at least one polyol with at least one triisocyanate to form a hydroxyl-terminated polyurethane prepolymer; and
(b) reacting the hydroxyl-terminated polyurethane prepolymer with at least one isocyanatosilane of formula (1) to endcap the hydroxyl groups on the hydroxyl-terminated polyurethane prepolymer with the isocyanatosilane,
OCN—R—Si—(X)m(R1)3−m (1)
wherein
m is 0, 1 or 2,
each R1 is independently from each other a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, or —OCH(R2)COOR3, wherein R2 is hydrogen or an alkyl group having 1 to 4 carbon atoms and R3 is a straight-chain or branched alkyl group having 1 to 8 carbon atoms,
each X is independently from each other an optionally substituted hydrocarbon group having 1 to 10 carbon atoms, which can be interrupted by at least one heteroatom, and
R is a difunctional organic group.

### Claim 2 (depends on 1)

The silylated polyurethane according to claim 1, wherein a molar ratio of the NCO groups of the triisocyanate to hydroxyl groups of the polyol is from 0.05 to 0.45.

### Claim 3 (depends on 1)

The silylated polyurethane according to claim 1, wherein said polyol is a polyether polyol.

### Claim 4 (depends on 1)

The silylated polyurethane according to claim 1, wherein said polyol has a number average molecular weight of from 500 to 20,000 g/mol.

### Claim 5 (depends on 1)

The silylated polyurethane according to claim 1, wherein said triisocyanate is derived from HDI, TDI, MDI, PDI, IPDI, or mixtures thereof.

### Claim 6 (depends on 1)

The silylated polyurethane according to claim 1, wherein said isocyanatosilane is selected from the group consisting of 3-isocyanatopropyltrimethoxysilane, 2-isocyanatoisopropyltrimethoxysilane, 4-isocyanato-n-butyltrimethoxysilane, 2-isocyanato-1,1-dimethylethyltrimethoxysilane, 1-isocyanatomethyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, 2-isocyanato-2-methylethyltriethoxysilane, 4-isocyanatobutyltriethoxysilane, 2-isocyanato-1,1-dimethylethyltriethoxysilane, 1-isocyanatomethyltriethoxysilane, 3-isocyanatopropylmethyld imethoxysilane, 3-isocyanatopropyldimethylmethoxysilane, 3-isocyanatopropylphenylmethylmethoxysilane, 1-isocyanatomethylmethyldimethoxysilane, 3-isocyanatopropylethyldiethoxysilane, 3-isocyanatopropylmethyldiethoxysilane, 1-isocyanatomethylmethyldiethoxysilane, and mixtures thereof.

### Claim 7 (depends on 1)

The silylated polyurethane according to claim 1, wherein said process comprises further step of adding a catalyst.

### Claim 8 (depends on 1)

An adhesive, sealant, or coating composition comprising the silylated polyurethane according to claim 1.

### Claim 9

An adhesive, sealant, or coating composition comprising:
a silylated polyurethane: and
optionally one or more additives selected from catalyst, plasticizer, stabilizer, antioxidant, filler, reactive diluent, drying agent, adhesion promoter, UV stabilizer, fungicide, flame retardant, rheological adjuvant, color pigment, color paste, and solvent;
wherein the composition has a viscosity of 40,000 mPas to 150,000 mPas and the silylated polyurethane is the reaction product of a mixture comprising:
(a) the hydroxyl terminated polyurethane prepolymer reaction product of a mixture comprising at least one polyol and at least one triisocyanate; and
(b) at least one isocyanatosilane of formula (1)
OCN—R—Si—(X)m(R1)3−m (1)
wherein
m is 0, 1 or 2,
each R1 is independently from each other a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, or —OCH(R2)COOR3, wherein R2 is hydrogen or an alkyl group having 1 to 4 carbon atoms and R3 is a straight-chain or branched alkyl group having 1 to 8 carbon atoms,
each X is independently from each other an optionally substituted hydrocarbon group having 1 to 10 carbon atoms, which can be interrupted by at least one heteroatom, and
R is a difunctional organic group.