Organosilicon compounds, process for their production and their use

a technology of organic silanes and compounds, applied in the field of organic silane compounds, can solve the problems of low hardness and dynamic rigidity of rubber compounds, the need to add alkyl silanes to rubber compounds, and the release of alcohol during and after bonding to fillers, etc., to achieve good dry performance, improve wet skid resistance, and improve the effect of hardness and dynamic rigidity

Inactive Publication Date: 2003-12-11
DEGUSSA AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Benefits of technology

0059] The rubber compound according to the invention can be used for the production of tire treads with improved, lower rolling resistance, improved wet skid resistance and equally good dry performance as compared with a similar rubber compound in which the organosilicon compound according to the invention is exchanged for bis-(3-triethoxysilylpropyl) tetrasulfide in a molar ratio relative to the silicon units of 1:1.8 to 1:2.7.
0060] The rubber compound according to the invention can be used for the production of tire treads with improved, lower rolling resistance and improved wet skid resistance with equally good abrasion resistance as compared with a similar rubber compound in which the organosilicon compound according to the invention is exchanged for bis-(3-triethoxysilylpropyl) tetrasulfide in a molar ratio relative to the silicon units of 1:1.8 to 1:2.7.
0061] The organosilicon compounds according to the invention have the advantage compared with organosilicon compounds according to DE 10137809 that hardness and dynamic rigidity E* are increased while tan .delta. 60.degree. C. (correlated with rolling resistance) remains the same.
0062] The organosilicon compounds according to the invention have the advantage that less methanol or ethanol is released than is the case with the known silanes while the reactivity remains the same. Due to their inactivity the non-volatile alcohols are not separated from the organosilicon compound or because of their non-volatility they remain in the polymer matrix. In both cases they are not released into the environment.
0063] In addition, the organosilicon compounds according to the invention have the advantage that there is no need to add alkyl silane as described in DE 10015309, since in the organosilicon compounds according to the invention having formula I and / or II no deterioration in processability, as in the case of e.g. 3-mercaptopropyl trimethoxysilane or 3-mercaptopropyl triethoxysilane, has been found.
0064] The rubber compounds according to the invention have the advantage as compared with rubber compounds containing bis-(3-triethoxysilylpropyl) tetrasulfide that dynamic rigidity is reduced and they are therefore especially suitable for winter tires (soft formulation).

Problems solved by technology

It is also known that the use of commercial silane coupling agents (DE 22 55 577) with three alkoxy substituents at the silicon atom leads to the release of considerable amounts of alcohol during and after bonding to the filler.
A disadvantage of the known mercaptosilanes according to DE 10015309 is the need to add alkyl silanes to rubber compounds in order to obtain particular properties.
A disadvantage of the known organosilicon compounds according to DE 10137809 is the low hardness and dynamic rigidity in rubber compounds.

Method used

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  • Organosilicon compounds, process for their production and their use
  • Organosilicon compounds, process for their production and their use
  • Organosilicon compounds, process for their production and their use

Examples

Experimental program
Comparison scheme
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example 1

[0066] A mixture consisting of 286.1 g 3-mercaptopropyl triethoxysilane (formula III where R=CH.sub.2CH.sub.3, R.sup.2=--CH.sub.2CH.sub.2CH.sub.2---), 313.1 g dodecanol (R.sup.1=--C.sub.12H.sub.25) and 154.4 g 1-tetradecanol (R.sup.1 =--C.sub.14H.sub.29) is heated with 140 .mu.l tetra-n-butyl orthotitanate to 110.degree. C. in a 1-litre flask in a rotary evaporator and ethanol that is produced is distilled off over 4 h in vacuo at 40 mbar. 636.86 g (99.0%) of a colorless liquid having formula I, where R=--CH.sub.2CH.sub.3, R.sup.1 =--C.sub.12.6H.sub.26.2, R.sup.2=--CH.sub.2CH.sub.2CH.sub.2--), is obtained.

example 2

[0067] Production and analysis of the rubber compounds according to the invention The formulation used for the rubber compounds is set out in Table 1 below. The unit phr denotes contents by weight, relative to 100 parts of the crude rubber used. The organosilicon compound according to the invention is added in equimolar quantities to 3-mercaptopropyl triethoxysilane relative to silicon. The general process for the production of rubber compounds and vulcanizates thereof is described in the book: "Rubber Technology Handbook", W. Hofmann, Hanser Verlag 1994.

1 TABLE 1 Compound 1 Compound 2 Reference Reference Compound 3 Stage 1 Buna VSL 5025-1 96 96 96 Buna CB 24 30 30 30 Ultrasil 7000 GR 80 80 80 3-mercaptopropyl 2.4 -- --triethoxysilane VP Si 208 2.5 -- --Organosilicon compound -- 5.7 --according to example 10 DE 10137809.2 Organosilicon compound -- -- 5.4 according to example 1 ZnO 2 2 2 Stearic acid 2 2 2 Naftolen 10 10 10 Vulkanox 4020 1.5 1.5 1.5 Protektor G35P 1 1 1 Stage 2 Batch...

example 3

[0076] 268.08 g 3-mercaptopropyl triethoxysilane and a mixture consisting of 313.05 g 1-dodecanol and 154.36 g 1 tetradecanol are placed in a 1-litre three-necked flask with distillation attachment at room temperature and 1.0 g toluene-p-sulfonic acid monohydrate is added. The solution is heated to 120.degree. C. The ethanol that is produced is continuously removed by distillation. Distillation is then performed in a rotary evaporator in vacuo at 80.degree. C. and 20 mbar. 638.7 g (99%) of a colorless liquid according to formula I is obtained, where R=--CH.sub.2CH.sub.3, R.sup.1=mixture of --C.sub.12H.sub.25 and --C.sub.14H.sub.29 in the ratio 2:1 and R.sup.2=--CH.sub.2CH.sub.2CH.sub.-2--.

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Abstract

Abstract Organosilicon compounds having the formula I and/or II wherein R<1 >is a mixture and the proportion of one component of the mixture is 10 to 50 mol %, are produced by reacting silanes having the formula III with mixtures of alcohols having the general formula R<1>-OH, with elimination of R-OH, and R-OH is continuously separated off from the reaction mixture by distillation. The organosilicon compounds can be used in rubber compounds.

Description

INTRODUCTION AND BACKGROUND[0001] The present invention concerns organosilicon compounds, a process for their production and their use.[0002] The use of silanes as coupling agents is known. Thus aminoalkyl trialkoxysilanes, methacryloxyalkyl trialkoxysilanes, polysulfanalkyl trialkoxysilanes and mercaptoalkyl trialkoxysilanes are used as coupling agents between inorganic materials and organic polymers, as crosslinking agents and surface modifiers (E. P. Plueddemann, "Silane Coupling Agents", 2.sup.nd Ed. Plenum Press 1982).[0003] These coupling agents or bonding agents form bonds to both the filler and the elastomer, thus creating a good interaction between the filler surface and the elastomer.[0004] It is also known that the use of commercial silane coupling agents (DE 22 55 577) with three alkoxy substituents at the silicon atom leads to the release of considerable amounts of alcohol during and after bonding to the filler. Since trimethoxy- and triethoxy-substituted silanes are ge...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07B61/00B60C1/00C07F7/18C08K5/00C08K5/548C08L21/00
CPCB60C1/0016C07F7/1836Y10S152/905C08K5/548C08L21/00C07F7/1804C07F7/18
Inventor KRAFCZYK, ROLANDDESCHLER, ULRICHLUGINSLAND, HANS-DETLEFPIETER, REIMUNDHASSE, ANDREMAYER, MELANIE
Owner DEGUSSA AG
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