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Blocked mercaptosilane hydrolyzates as coupling agents for mineral-filled elastomer compositions

A technology of mercaptosilane and condensation products, which is applied in the direction of silicon organic compounds, compounds of group 5/15 elements of the periodic table, compounds of group 4/14 elements of the periodic table, etc. question

Inactive Publication Date: 2005-08-31
MOMENTIVE PERFORMANCE MATERIALS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the patent stipulates that the components of the above general structure must be used in combination with functionalized siloxane
Furthermore, the patent does not disclose or suggest the use of compounds of formula (1P) as potential mercaptosilane coupling agents, nor does it disclose or suggest the use of these compounds in any manner that would yield advantages in using them as potential mercaptosilanes
[0010] JP 63270751 A2 discloses the general formula compound CH 2 =C(CH 3 )C(=O)S(CH 2 ) 6 Si(OCH 3 ) 3 Use in tire tread compositions, however these compounds are not ideal because of the α,β unsaturation of the thioester carbonyls with the potential for unwanted polymerization during the mixing process or during storage

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0321] Example 1 Homogeneous preparation of the condensate of 3-acetylthio-1-propyltriethoxysilane

[0322] The crude starting material of 3-acetylthio-1-propyltriethoxysilane was first refined from sodium ethoxide by flashvacuum distillation. The distillate was distilled again. An initial forecut of volatiles was withdrawn and the bulk of the distillate remained as a clear colorless liquid, which was used as starting material for the preparation of the condensate. Under stirring, to a homogeneous mixture of 3-acetylthio-1-propyltriethoxysilane (74.35 g, 0.2525 mol) and absolute ethanol (70 g) was added an appropriate amount of water (2.27 g, 0.126 mol) . The mixture was left to stand at room temperature for 6 weeks. After this time, volatiles were removed by rotary evaporation.

Embodiment 2

[0323] Example 2 Heterogeneous Preparation of the Condensate of 3-Acetylthio-1-Propyltriethoxysilane

[0324] The crude starting material of 3-acetylthio-1-propyltriethoxysilane was first purified from sodium ethoxide by vacuum flash evaporation. The distillate was distilled again. The initial foreflux of volatiles was withdrawn and the overall distillate remained a clear colorless liquid which was used as starting material for the preparation of the condensate. A biphasic mixture of 3-acetylthio-1-propyltriethoxysilane (68.3 g, 0.232 mol) and water (49 g, 2.7 mol) was stirred at ambient temperature for 6 weeks. Thereafter, the liquid layer was separated from the separatory funnel. Volatiles were removed from the organic phase by rotary evaporation.

Embodiment 3

[0325] Example 3 Homogeneous preparation of 8-octanoylthio-1-propyltriethoxysilane condensate

[0326] 8-Octanoylthio-1-propyltriethoxysilane (240 g, 0.66 mol) was added to a homogeneous mixture of absolute ethanol (54 g) and water (5.93 g, 0.329 mol) with stirring middle. The mixture was allowed to stand at ambient temperature for 6 weeks. After this time, volatiles were removed by rotary evaporation. The product was then purified by vacuum flashing to remove the forestrip and retain the non-volatile portion of the sample. The former contains most of the impurities of ethyl octanoate, 3-mercapto-1-propyltriethoxysilane and 3-chloro-1-propyltriethoxysilane. By comparing with the pure samples of each impurity, the GC (gas chromatography) confirmed. GC analysis results (area%): Si-O-Si siloxane "dimer" of 8-octanoylthio-1-propyltriethoxysilane 46.4%; 8-octanoylthio-1- Propyltriethoxysilane is 33.0%; 1-diethoxy-1-sila-2-thiolane is 0.2%; bis-3-triethoxysilyl-1-propyldi Su...

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Abstract

The present invention discloses the use of blocked mercaptosilane condensates in mineral-filled elastomeric compositions. The advantage of using these blocked mercaptosilane condensates over prior art blocked mercaptosilanes is the low release of volatile organic compounds during the elastomer compounding process and the need to use a small amount of coupling.

Description

field of invention [0001] The present invention relates to the composition, preparation and use of latent mercaptosilane coupling agents containing siloxane linkages in elastomeric compositions. Compared to the prior art, these coupling agents represent an improvement in that their use is accompanied by a reduced emission of volatile organic compounds (VOC). Background technique [0002] Latent mercaptosilane coupling agents known in the art contain hydrolyzable groups that can be converted into volatile by-products when the coupling agent reacts with fillers used in rubber compositions. [0003] Most techniques for using sulfur-containing coupling agents in rubber involve silanes containing one or more of the following bond types: S-H (mercapto), S-S (disulfide or polysulfide), or C=S (sulfur Substituted carbonyl). At significantly reduced usage levels, mercaptosilanes provide superior coupling; however, their high chemical reactivity with organic polymers results in unac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G77/28C08K5/54C07F7/18B60C1/00C07F7/08C07F9/40C08K3/00C08K5/548C08L83/08C08L101/00
CPCC07F9/4012C08K5/548C07F7/0885C08K3/0033B60C1/00C08K3/013C07F7/0876C08L21/00C08G77/28C08K5/54
Inventor 理查德·W·克鲁斯
Owner MOMENTIVE PERFORMANCE MATERIALS INC