# US 2023/0057557 A1 · Silirane compounds as stable silylene precursors and their use in the catalyst-free preparation of siloxanes

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

- Number: US 2023/0057557 A1
- Document ID: US20230057557A1
- Status: Published application
- Kind: A1
- Application number: 17/781,838
- Filed: 2019-12-04
- Published: 2023-02-23
- Earliest claimed: 2019-12-04
- Assignees: Wacker Chemie AG
- Applicants: Wacker Chemie AG
- Inventors: Richard WEIDNER; Fabian Andreas David Herz; Matthias Fabian NOBIS; Bernhard RIEGER
- Web page: https://patentgrep.com/patent/US20230057557A1

## CPC

- C07F 7/0807: {comprising Si as a ring atom}
- C07F 7/0838: {Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21)}
- C07F 7/0889: {Reactions not involving the Si atom of the Si-O-Si sequence}
- C07F 7/10: containing nitrogen {having a Si-N linkage}
- C07F 7/18: Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F 7/21: Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
- C08G 77/16: to hydroxy groups
- C08G 77/388: containing nitrogen
- C08G 77/50: by carbon linkages
- C08G 77/54: Nitrogen-containing linkages
- C08K 5/5445: containing at least one Si-N bond
- C08K 5/549: containing silicon in a ring
- C07F 7/12: Organo silicon halides
- C08G 77/12: containing silicon bound to hydrogen
- 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
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

A silirane-functionalized compound that consists of a substrate to which a least two silirane groups of the formula (1) are covalently bonded, a mixture containing the silirane-functionalized compounds, and a process for preparing siloxanes using the mixture are described herein.

## Claims

### Claim at position 1

1-12. (canceled)

### Claim 13

Silirane-functionalized compounds consisting of a substrate on which at least two silirane groups of the formula (I)
are covalently bonded,
where in formula (I) the index n adopts a value of 0 or 1;
and where the radical Ra is a divalent C1-C20 hydrocarbon radical;
and where the radical R1 is selected from the group consisting of (i) C1-C20 hydrocarbon radical, (ii) C1-C20 hydrocarbonoxy radical, (iii) silyl radical —SiRaRbRc, in which the radicals Ra,Rb,Rc independently of one another are selected from the group consisting of C1-C6 hydrocarbon radical, (iv) amine radical —NRx2, in which the radicals Rx independently of one another are selected from the group consisting of (iv.i) hydrogen, (iv.ii) C1-C20 hydrocarbon radical, and (iv.iii) silyl radical —SiRaRbRc, in which the radicals Ra,Rb,Rc independently of one another are a C1-C6 hydrocarbon radical, and (v) imine radical —N═CR1R2, in which the radicals R1,R2 independently of one another are selected from the group consisting of (v.i) hydrogen, (v.ii) C1-C20 hydrocarbon radical and (v.iii) silyl radical —SiRaRbRc, in which the radicals Ra,Rb,Rc independently of one another are a C1-C6 hydrocarbon radical; and
where the radicals R2,R3,R4,R5 independently of one another are selected from the group consisting of (i) hydrogen, (ii) halogen, and (iii) C1-C20 hydrocarbon radical, in which the radicals R2 and R4 may also be part of a cyclic radical,
where the compound of the formula
in which Bbt is 2,6-[CH(SiMe3)2]-4-[C(SiMe3)3]—C2H6 is excluded.

### Claim 14 (depends on 13)

The silirane-functionalized compounds as claimed in claim 13, characterized in that the substrate is selected from the group consisting of organosilicon compounds, hydrocarbons, silicas, glass, sand, stone, metals, semimetals, metal oxides, mixed metal oxides, and carbon-based oligomers and polymers.

### Claim 15 (depends on 14)

The silirane-functionalized compounds as claimed in claim 14, characterized in that the substrate is selected from the group consisting of silanes, siloxanes, precipitated silica, fumed silica, glass, hydrocarbons, polyolefins, acrylates, polyacrylates, polyvinyl acetates, polyurethanes and polyethers composed of propylene oxide and/or ethylene oxide units.

### Claim 16 (depends on 13)

The silirane-functionalized compounds as claimed in claim 13, characterized in that they are silirane-functionalized organosilicon compounds selected from the group consisting of compounds of the general formula (II)
(SiO4/2)a(RxSiO3/2)b(R′SiO3/2)b′(Rx2SiO2/2)c(RxR′SiO2/2)c′(R′2SiO2/2)c″(Rx3SiO1/2)d(R′Rx2SiO1/2)d′(R′2RxSiO1/2)d″(R′3SiO1/2)d″′ (II),
in which the radicals Rx independently of one another are selected from the group consisting of (i) hydrogen, (ii) halogen, (iii) unsubstituted or substituted C1-C20 hydrocarbon radical and (iv) unsubstituted or substituted C1-C20 hydrocarbonoxy radical;
and in which the indices a, b, b′, c, c′, c″, d, d′, d″, d″′ indicate the number of the respective siloxane unit in the compound and independently of one another are an integer in the range from 0 to 100 000, with the proviso that the sum of a, b, b′, c, c′, c″, d, d′, d″, d′″ together adopts a value of at least 2 and at least one of the indices b′, c′, d′ is ≥2 or at least one of the indices c″, d″ or d″′ is other than 0;
and the radicals R′ are a silirane group of the formula (IIa)
in which the index n adopts a value of 0 or 1; and
in which the radical Ra is a divalent C1-C20 hydrocarbon radical;
and where the radical R1 is selected from the group consisting of (i) C1-C20 hydrocarbon radical, (ii) C1-C20 hydrocarbonoxy radical, (iii) silyl radical —SiRaRbRc, in which the radicals Ra,Rb,Rc independently of one another are a C1-C6 hydrocarbon radical, (iv) amine radical —NRx2, in which the radicals Rx independently of one another are selected from the group consisting of (iv.i) hydrogen, (iv.ii) C1-C20 hydrocarbon radical, and (iv.iii) silyl radical —SiRaRbRc, in which the radicals Ra,Rb,Rc independently of one another are a C1-C6 hydrocarbon radical, and (v) imine radical —N═CR1R2, in which the radicals R1,R2 independently of one another are selected from the group consisting of (v.i) hydrogen, (v.ii) C1-C20 hydrocarbon radical and (v.iii) silyl radical —SiRaRbRc, in which the radicals Ra,Rb,Rc independently of one another are a C1-C6 hydrocarbon radical; and
where the radicals R2,R3,R4,R5 independently of one another are selected from the group consisting of (i) hydrogen, (ii) halogen, and (iii) C1-C20 hydrocarbon radical, in which the radicals R2 and R4 may also be part of a cyclic radical.

### Claim 17 (depends on 16)

The silirane-functionalized compounds as claimed in claim 16, where in formula (II) the indices a, b, b′, c, c′, c″, d, d″ and d″′ adopt a value of 0 and the index d′ adopts a value of 2; and where in formula (IIa) the index n adopts a value of 1, and the radical Ra is a C1-C3 alkylene radical, and the radical R1 is selected from the group consisting of (i) C1-C6 hydrocarbon radical and (ii) amine radical —N(SiRaRbRc)2, in which the radicals Ra,Rb,Rc independently of one another are a C1-C6 hydrocarbon radical, and the radicals R2,R3,R4,R5 independently of one another are selected from the group consisting of (i) hydrogen and (ii) C1-C6 alkyl radical, in which the radicals R2 and R4 may also be part of a cyclic radical.

### Claim 18 (depends on 17)

The silirane-functionalized compounds as claimed in claim 17, where in formula (IIa) the radical Ra is an ethylene radical; and the radical R1 is selected from the group consisting of (i) C1-C6 alkyl radical and (ii) —N(SiMe3)2; and the radicals R2,R3,R4,R5 independently of one another are selected from the group consisting of (i) hydrogen and (ii) C1-C6 alkyl radical, in which the radicals R2 and R4 may also be part of a hexenyl radical.

### Claim 19 (depends on 16)

The silirane-functionalized compounds as claimed in claim 16, which is selected from the following compounds
SV1, SV2 and SV3.

### Claim 20 (depends on 1, 2, 3, 4, 5, 6, 7)

A mixture comprising
a) at least one silirane-functionalized compound as claimed in any of claims 1-7; and
b) at least one compound A which has in each case at least two radicals R′, where the radicals R′ independently of one another are selected from the group consisting of (i) —Si—H, (ii) —OH, (iii) —CxH2x—OH, in which x is an integer in the range of 1-20, (iv) —CxH2x—NH2, in which x is an integer in the range of 1-20, (v) —SH, and (vi) —Ran—CR═CR2, in which Ra is a divalent C1-C20 hydrocarbon radical and the index n adopts a value of 0 or 1 and the radicals R independently of one another are selected from the group consisting of (vi.i) hydrogen and (vi.ii) C1-C6 hydrocarbon radical.

### Claim 21 (depends on 20)

The mixture as claimed in claim 20, where the compound A is selected from functionalized siloxanes of the general formula (III)
(SiO4/2)a(RxSiO3/2)b(R′SiO3/2)b′(Rx2SiO2/2)c(RxR′SiO2/2)c′(R′2SiO2/2)c″(Rx3SiO1/2)d(R′Rx2SiO1/2)d′(R′2RxSiO1/2)d″(R′3SiO1/2)d″′ (III),
in which the radicals Rx independently of one another are selected from the group consisting of (i) halogen, and (ii) unsubstituted or substituted C1-C20 hydrocarbon radical; and
in which the radicals R′ independently of one another are selected from the group consisting of (i) hydrogen, (ii) —OH, (iii) —CxH2x—OH, in which x is an integer in the range of 1-20, (iv) —CxH2x—NH2, in which x is an integer in the range of 1-20, (v) —SH, and (vi) —Ran—CR═CR2, in which Ra is a divalent C1-C20 hydrocarbon radical and the index n adopts a value of 0 or 1 and the radicals R independently of one another are selected from the group consisting of (vi.i) hydrogen and (vi.ii) C1-C6 hydrocarbon radical; and
in which the indices a, b, b′, c, c′, c″, d, d′, d″, d″′ indicate the number of the respective siloxane unit in the compound and independently of one another are an integer in the range from 0 to 100 000, with the proviso that the sum of a, b, b′, c, c′, c″, d, d′, d″, d″′ together adopts a value of at least 2 and at least one of the indices b′, c′, d′ is ≥2 or at least one of the indices c″, d″ or d′″ is other than 0.

### Claim 22 (depends on 21)

A process for preparing siloxanes, comprising the following steps:
(i) providing a mixture as claimed in claim 21, and
(ii) reacting the mixture by thermal, photochemical or catalytic activation.

### Claim 23 (depends on 22)

The process as claimed in claim 22, where the activation takes place thermally and the temperature is in a range from 60° C. to 200° C.

### Claim 24 (depends on 22)

The process as claimed in claim 22, where the molar ratio of silirane groups to functional groups in the siloxane is in a range of 4:1-1:4.