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Siloxane oligomers, a process for their production and their use

a technology of siloxane oligomers and production processes, applied in the field of siloxane oligomers, can solve the problems of siloxane oligomers, release of considerable amounts of alcohol during the mixing process,

Inactive Publication Date: 2003-01-23
DEGUSSA AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0048] The siloxane oligomers according to the invention have the advantages of a low release of alcohol in the reaction in rubber and the fact that they contain functionalized alkyl groups for subsequent chemical reactions.

Problems solved by technology

Furthermore it is known that the use of commercially available silane coupling agents (DE 22 55 577) with three alkoxy substituents on the silicon atom leads to the release of considerable amounts of alcohol during the mixing process.
Disadvantages of the known siloxane oligomers are

Method used

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  • Siloxane oligomers, a process for their production and their use
  • Siloxane oligomers, a process for their production and their use
  • Siloxane oligomers, a process for their production and their use

Examples

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Effect test

example 1

Reaction of a Chloropropyltrichlorosilane-Propyltrichlorosilane Mixture with Water and Ethanol

[0049] 106.7 g of chloropropyltrichlorosilane and 193.6 g of propyltrichlorosilane are added as a mixture to a 1 liter capacity three-necked flask equipped with stirrer, cooler and nitrogen inlet tube. A solution of 380 ml of ethanol and 17.2 g of water is added dropwise within 50 minutes while cooling. The reaction mixture is then heated for 4 hours under reflux and the hydrogen chloride gas is expelled. 228.0 g of a clear, pale yellow liquid are obtained after removing the excess ethanol. The ratio of propyl radical to chloropropyl radical is 2 to 1.

[0050] .sup.1H-NMR (CDCl.sub.3): .delta. 0.60 (m, 4H, Si--CH.sub.2--CH.sub.2--CH.sub.3), 0.75 (m, 2H, Si--CH.sub.2--CH.sub.2--C-H.sub.2--Cl), 0.95 (t, 6H, .sup.3J.sub.H-H=7 Hz, Si--CH.sub.2--CH.sub.2--C-H.sub.3), 1.20 (m, 12H, CH.sub.3--CH.sub.2--O--Si), 1.45 (m, 4H, Si--CH.sub.2--CH.sub.2--CH.sub.3), 1.85 (m, 2H, Si--CH.sub.2--CH.sub.2--C-H.s...

example 2

Reaction of a Chloropropyltrichlorosilane-Octyltrichlorosilane Mixture with Water and Ethanol

[0051] 106.7 g of chloropropyltrichlorosilane and 111.8 g of octyltrichlorosilane are added as a mixture to a 1 liter capacity three-necked flask equipped with stirrer, cooler and nitrogen inlet tube. A solution of 240 ml of ethanol and 10.7 g of water is added dropwise within 40 minutes while cooling. The reaction mixture is then heated for 4 hours under reflux and the hydrogen chloride gas is expelled. 182.3 g of a clear, colorless liquid are obtained after removing the excess ethanol. The ratio of octyl radicals to chloropropyl radicals is 1 to 1.

[0052] .sub.1H-NMR (CDCl.sub.3): .delta. 0.60 (m, 2H, Si--CH.sub.2--(CH.sub.2).sub.6--CH.sub.3), 0.80 (m, 2H, Si--CH.sub.2--CH.sub.2--CH.sub.2--Cl), 0.90 (t, 3H, .sup.3J.sub.H-H=7 Hz, Si--CH.sub.2--(CH.sub.2).sub.6--CH.sub.3), 1.25 (m, 9H, CH.sub.3--CH.sub.2--O--Si), 1.3-1.5 (m, 12H, Si--CH.sub.2--(CH.sub.2).sub-.6--CH.sub.3), 1.85 (m, 2H, Si--CH...

example 3

Reaction of a Chloropropyltrichlorosilane-Hexadecyltrichlorosilane Mixture with Water and Ethanol

[0053] 106.7 g of chloropropyltrichlorosilane and 74.1 g of hexadecyltrichlorosilane are added as a mixture to a 1 liter capacity three-necked flask equipped with stirrer, cooler and nitrogen inlet tube. A solution of 180 ml of ethanol and 8.0 g of water is added dropwise within 50 minutes while cooling. The reaction mixture is then heated for 4 hours under reflux and the hydrogen chloride gas is expelled. 145.3 g of a clear, pale yellow liquid are obtained after removing the excess ethanol. The ratio of hexadecyl radicals to chloropropyl radicals is 1 to 2.5.

[0054] .sup.1H-NMR (CDCl.sub.3): .delta. 0.65 (m, 2H, Si--CH.sub.2--(CH.sub.2).sub.14--CH.sub.3), 0.80 (m, 5H, Si--CH.sub.2--CH.sub.2--CH.sub.2--Cl), 0.85 (t, 3H, .sup.3J.sub.H-H=7 Hz, Si--CH.sub.2--(CH.sub.2).sub.14--CH.sub.3), 1.25 (m, 15H, CH.sub.3--CH.sub.2--O--Si), 1.3-1.5 (m, 28H, Si--CH.sub.2--(CH.sub.2).sub-.14--CH.sub.3), 1...

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Abstract

Siloxane oligomers of the general formula I or II wherein at least one functionalized alkyl group is present per oligomer molecule. The siloxane oligomers are produced by oligomerization of halogenalkyltrihalogensilanes, and co-optionally co-oligomerized with (C1-C18)-alkyl-, phenyl-, aryl- or aralkyl-trihalogensilanes and / or silicon tetrachloride, in the presence of alcohol and water, following which the halogenalkyl function is optionally modified in a further step. The siloxane oligomers can be used as coupling agents in rubber mixtures or as building preservation agents.

Description

INTRODUCTION AND BACKGROUND[0001] The present invention relates to siloxane oligomers, a process for their production as well as their use.[0002] It is known to employ silanes as coupling agents. Thus, aminoalkyltrialkoxysilanes, methacryloxyalkyltrialkoxysilanes, polysulfanalkyltrialkoxysilanes, as well as mercaptoalkyltrialkoxysilanes are used as coupling agents between inorganic materials (e.g. glass fibres, metals, oxidic fillers) and organic polymers (e.g. thermosetting plastics, thermoplastic materials, elastomers) and / or as crosslinking agents and surface modification agents.[0003] These coupling or bonding agents form bonds with the filler as well as the elastomer and thereby produce a good interaction between the filler surface and the elastomer. They reduce the viscosity of the mixture and facilitate the dispersion of the filler.[0004] Furthermore it is known that the use of commercially available silane coupling agents (DE 22 55 577) with three alkoxy substituents on the ...

Claims

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Application Information

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IPC IPC(8): C07F7/10C07F7/08C07F7/12C07F7/18C07F7/21C08G77/04C08G77/28C08K3/04C08K3/34C08L21/00C08L83/04
CPCC08G77/04C08G77/22C08G77/28C08L21/00C08L2666/14C08L83/04C08L83/08
Inventor KRAFCZYK, ROLANDTREFFEISEN, BJORNMONKIEWICZ, JAROSLAW
Owner DEGUSSA AG
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