# US 9,751,900 B2 · Hydroxysilane and polymer containing silane groups

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- Number: US 9,751,900 B2
- Document ID: US9751900B2
- Status: Granted
- Kind: B2
- Application number: 14/891,819
- Filed: 2014-05-21
- Published: 2016-04-14
- Granted: 2017-09-05
- Earliest claimed: 2013-05-22
- Assignees: Sika Technology AG
- Applicants: Sika Technology AG
- Inventors: Andreas Kramer; Urs Burckhardt; Ursula Stadelmann
- Web page: https://patentgrep.com/patent/US9751900B2

## CPC

- C07F 7/0834: {Compounds having one or more O-Si linkage (for compounds with C-O-Si linkages see C07F7/18)}
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- C07F 7/1872: {Preparation; Treatments not provided for in C07F7/20}
- C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G 18/4866: {having a low unsaturation value}
- 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}
- C08G 18/837: {by silicon containing compounds}
- C08G 77/26: nitrogen-containing groups
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Special hydroxysilanes, which can be obtained by reacting β-(3,4-epoxycyclohexyl)alkyltrialkoxysilanes with secondary amines, and adducts of the hydroxysilanes in the form of polymers containing silane groups. The hydroxysilanes can be produced having high purity in a simple process and are very stable in storage after production. The polymers containing silane groups that can be obtained by means of the hydroxysilanes have advantageous properties. The polymers enable moisture-curing compositions, which contain no isocyanate groups and which are suitable as elastic adhesives and sealants.

## Claims

### Claim 1

A hydroxysilane of the formula (I)
where
either R′ is a radical of the formula (II) and R″ is hydrogen or R′ is hydrogen and R″ is a radical of the formula (II);
R1 and R2 are either each individually an alkyl radical having 1 to 12 carbon atoms and optionally having heteroatoms in the form of ether oxygen, thioether sulfur or tertiary amine nitrogen,
or together are an alkylene radical having 2 to 12 carbon atoms and optionally having heteroatoms in the form of ether oxygen, thioether sulfur or tertiary amine nitrogen;
R3 is a linear or branched alkylene or cycloalkylene radical having 1 to 20 carbon atoms, optionally having aromatic moieties, and optionally having one or more heteroatoms;
R4 is an alkyl group having 1 to 8 carbon atoms;
R5 is an alkyl group having 1 to 10 carbon atoms and optionally having one or more ether oxygen heteroatoms; and
x is 0 or 1 or 2.

### Claim 2 (depends on 1)

A hydroxysilane as claimed in claim 1, wherein R1 and R2 are either individually 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 2-(2-methoxyethoxy)ethyl, 2-octyloxyethyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, 2-ethylhexyl or N,N-dimethylaminopropyl, or together with inclusion of the nitrogen atom are an optionally substituted pyrrolidine, piperidine, hexamethyleneimine, morpholine, thiomorpholine or 4-methylpiperazine ring.

### Claim 3 (depends on 1)

A hydroxysilane as claimed in claim 1, wherein R3 is an ethylene radical.

### Claim 4 (depends on 1)

A hydroxysilane as claimed in claim 1, wherein R5 is a methyl group or an ethyl group.

### Claim 5 (depends on 1)

A hydroxysilane as claimed in claim 1, wherein x is 1 or 0.

### Claim 6 (depends on 1)

A process for preparing a hydroxysilane as claimed in claim 1, which comprises reacting at least one epoxysilane of the formula (III) with at least one amine of the formula (IV)

### Claim 7 (depends on 1)

An adduct obtained from the reaction of a hydroxysilane as claimed in claim 1 with at least one compound containing at least one reactive group, selected from the group consisting of isocyanate, epoxide, acryloyl, methacryloyl, anhydride, carboxylic acid, ester, carbonate and cyclocarbonate groups.

### Claim 8 (depends on 7)

The adduct as claimed in claim 7, wherein it is a polymer which has end groups of the formula (VI) and is free of isocyanate groups

### Claim 9 (depends on 8)

The adduct as claimed in claim 8, wherein the polymer has a molecular weight in the range from 1′000 to 30′000 g/mol.

### Claim 10 (depends on 8)

The adduct as claimed in claim 8, wherein the polymer has a majority of polyoxyalkylene units.

### Claim 11 (depends on 8)

The adduct as claimed in claim 8, wherein a majority of the end groups of the formula (VI) are bonded to cycloaliphatic radicals.

### Claim 12 (depends on 8)

The adduct as claimed in claim 8, wherein the polymer has 1 to 4 end groups of the formula (VI).