Epoxy-functional alkoxysilanes, method for the production and use thereof

Patent metadata

Field	Value
Publication number	US-10919919-B2
Application number	US-201816756383-A
Country	US
Kind code	B2
Filing date	Sep 26, 2018
Priority date	Oct 19, 2017
Publication date	Feb 16, 2021
Grant date	Feb 16, 2021

Abstract

Novel epoxy-functional alkoxysilanes have, for example, formulae II, III, IV, V, and VI.

First claim

The invention claimed is:

1. An epoxy-functional alkoxysilane of formulae II, I, IV, V, and/or VI:

wherein R represents a methyl or an ethyl group.

2. A process for producing at least one epoxy-functional alkoxysilane selected from the group consisting of formulae II, III, IV, V, and VI according to claim 1 , the process comprising:
reacting an epoxy-functional compound of formula I

with a hydrogentrialkoxysilane in the presence of a noble-metal-containing hydrosilylation catalyst,
optionally with addition of at least one solvent/diluent, and
optionally with addition of a promoter, and

subsequently obtaining a hydrosilylation product.

3. The process according to claim 2 , wherein the hydrogentrialkoxysilane is hydrogentrimethoxysilane or hydrogentriethoxysilane.

4. The process according to claim 2 , wherein the epoxy-functional compound of formula I relative to hydrogentrialkoxysilane is employed in a molar ratio of 1:0.8 to 1:100.

5. The process according to claim 2 , wherein the reaction is performed in the presence of the noble-metal-containing hydrosilylation catalyst selected from the group consisting of Pt, Pd, Rh, and combinations thereof, and
wherein the noble-metal-containing hydrosilylation catalyst may be homogeneous or heterogeneous.

6. The process according to claim 2 , wherein the noble-metal-containing hydrosilylation catalyst is a homogeneous catalyst which is employed in a noble metal to hydrogenalkoxysilane molar ratio of 1:1,000,000 to 1:100.

7. The process according to claim 2 , wherein the at least one solvent/diluent is added, and is selected from the group consisting of xylene, toluene, heptane, octane, nonane, and a C 7 to C 9 hydrocarbons mixture.

8. The process according to claim 2 , wherein at least one promoter is employed.

9. The process according to claim 2 , wherein the reaction is performed at a temperature in a range from 80° C. to 200° C. and at a pressure up to 4 bar abs.

10. The process according to claim 2 , wherein proportions of still-present components, having a boiling point below 180° C. at 1 bar, are removed from a product mixture obtained in the reaction by distillation under reduced pressure and a target product/a mixture of target products is obtained as bottoms product from the distillation, or
depending on the boiling point, as tops product from a distillation unit used, and
wherein, if a heterogeneous catalyst is used for the reaction, the heterogeneous catalyst is removed before distillation.

11. The process according to claim 2 , wherein the process is performed discontinuously in a stirred tank reactor.

12. An epoxy-functional alkoxysilane selected from the group consisting of formula II, III, IV, V and VI, or a mixture of at least two epoxy-functional alkoxysilanes selected from the group consisting of formulae II, III, IV, V, and VI, obtainable according to claim 2 .

13. A method for modification and/or coating of surfaces, for coating of glass fibres, for coating of metals and metal alloys, for protection from corrosion, for silanization of fillers and pigments, for production of adhesives and sealants, for production of composites and/or compounds, for production of corrosion protectants, as crosslinkers, as adhesion promoters, as primers and as an additive for paints and lacquers, the method comprising:
coating or modifying surfaces with at least one epoxy-functional alkoxysilane selected from the group consisting of formula II, III, IV, V, or VI according to claim 1 , or
coating glass fibres, metals, or metal alloys with the at least one epoxy-functional alkoxysilane, wherein the coating protects the metals or metal alloys from corrosion, or
silanizing fillers and pigments with the at least one epoxy-functional alkoxysilane, or
producing adhesives, sealants, composites, compounds, and/or corrosion protectants which comprise the at least one epoxy-functional alkoxysilane, or
adding the at least one epoxy-functional alkoxysilane to paints or lacquers as a crosslinker, adhesion promoter, or primer.

14. The process according to claim 4 , wherein the epoxy-functional compound of formula I relative to hydrogentrialkoxysilane is employed in a molar ratio of 1:2.5 to 1:5.

15. The process according to claim 5 , wherein the noble-metal-containing hydrosilylation catalyst is selected from the group consisting of a Pt-containing homogeneous catalyst, a catalyst based on hexachloroplatinic(IV) acid, or a combination thereof.

16. The process according to claim 15 , wherein the noble-metal-containing hydrosilylation catalyst is Karstedt's catalyst, optionally in xylene or toluene, having a content of Pt(0) of 0.01% to 20% by weight.

17. The process according to claim 5 , wherein the noble-metal-containing hydrosilylation catalyst is a noble metal applied to a solid catalyst support, as a heterogeneous catalyst.

18. The process according to claim 17 , wherein the noble metal applied to the solid catalyst support is Pt supported on activated carbon.

19. The process according to claim 8 , wherein the at least one promoter is selected from the group consisting of an organic acid having 2 to 10 carbon atoms, acetic acid, pentanoic acid, and hexanoic acid.

20. The process according to claim 10 , wherein the heterogeneous catalyst is removed before the distillation by filtration and/or centrifuging.

Assignees

• Evonik Operations Gmbh

Inventors

• Rudek Markus
• Witzsche Susann
• Bade Stefan
• Standke Burkhard
• Störger Reiner

Classifications

• C09D183/06

  containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence) · CPC title

• C07F7/1876 Primary

  by reactions involving the formation of Si-C linkages · CPC title

• C08K5/5415

  containing at least one Si—O bond · CPC title

• B01J31/28

  of the platinum group metals, iron group metals or copper · CPC title

• C07F7/1804 Primary

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title