Title of Invention	ORGANOSILICON COMPOUNDS AND A PROCESS FOR THE PRODUCTION THEREOF
Abstract	Organosilicon compounds of the general formula I and/or II are produced by reacting silanes of the general formula III with alcohols of the general formula R'-OH, with elimination of R-OH, and R-OH is continuously separated from the reaction mixture by distillation. The organosilicon compounds may be used in rubber mixtures.

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Organosilicon compounds This invention relates to organosilicon compounds, to a process for the production thereof and to the use thereof. It is known to use silanes as adhesion promoters. Aminoalkyltrialkoxysilanes, such as for example 3-amino- propyltrimethoxysilane and 3-aminopropyltriethoxysilane, methacryloxyalkyltrialkoxysilanes, such as for example 3-methacryloxypropyltrimethoxysilane, polysulfane alkyltrialkoxysilanes, such as for example bis[3-triethoxy- silylpropyl]polysulfane and bis[3-triethoxysilylpropyl]- disulfane and mercaptoalkyltrialkoxysilanes, such as for example 3-mercaptopropyltrimethoxysilane and 3-mercapto- propyltriethoxysilane as adhesion promoters between inorganic materials, for example glass fibres, metals or oxide fillers, and organic polymers, such as thermosets, thermoplastics and elastomers, or as crosslinking agents and surface-modifying agents. These adhesion promoters or coupling or bonding agents form bonds both with the filler and with the elastomer, so ensuring good interaction between the filler surface and the elastomer. They reduce mixture viscosity and facilitate filler dispersion. It is moreover known that using conventional commercial silane adhesion promoters (DE 22 55 577) having three alkoxy substituents on the silicon atom results in the release of considerable quantities of alcohol during and after bonding to the filler. Since the silanes used are generally trimethoxy- and triethoxy-substituted, considerable quantities of the corresponding alcohols methanol and ethanol are released. It is furthermore known that methoxy- and ethoxy- substituted silanes are more reactive than the corresponding long-chain alkoxy-substituted silanes and are thus able to bond themselves to the filler more rapidly, such that, on economic grounds, it is not possible to dispense with the use of methoxy- and ethoxy-substituted silanes. One disadvantage of known organosilicon compounds is the release of volatile alcohols, such as methanol and ethanol, into the environment during and after bonding of the silane to the filler. The object of the invention is to produce organosilicon compounds which release smaller quantities of volatile alcohol during bonding to the filler and simultaneously have elevated reactivity. The present invention provides organosilicon compounds of the general formula I and/or II wherein R is a mothyl or ethyl group, R' is identical or different and is a C9-C30 branched or unbranched monovalent alkyl or alkenyl group, aryl group aralkyl group branched or unbranched C2-C30 alkyl ether group, branched or unbranched C2-C30 alkyl polyether group or R' ' ' si , where R' ' ' is C1-C30 branched or unbranched alkyl or alkenyl group, aralkyl group or aryl group, R" is a branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic divalent C1-C30 hydrocarbon group, X is NH13mh where 1,2, 3 and m =1; O(C=O)-R'' where n = 1 and m = 1, SH where n = 1 and m = 1, S where n = 2 and m = 1-10 and mixtures thereof, S(C=O)-R'' where n = 1 and m = 1 on H where n = 1 and m = 1. R" may mean CH2, CH2CH2, CH2CH2CH2, CH2CH2CH2CH2, CH(CH3), CH2CH(CH3), C(CH3)2, CH(C2H5), CH2CH2CH (CH3) , CH2CH (CH3) CH2 or Organosilicon compounds according to the invention of the formula I or II may be: The present invention also provides a process for the production of the organosilicon compounds according to the invention, which process is characterised in that silanes of the general formula III in which R, R", X, m and n have the above-stated meaning, are reacted with alcohols of the general formula R'-OH, in which R' exhibits the above-stated meaning, with elimination of R-OH, and R-OH is continuously separated from the reaction mixture by distillation. In the process according to the invention, a mixture may be obtained in which none, one, two or three of the RO groups are replaced by R'O groups. The ratio of the RO groups to R'O groups may be determined by the molar ratio of the silane of the general formula III to the alcohol of the general formula R'-OH. For example, when n = 1, an organosilicon compound having an average composition according to the formula I may be produced by reacting two mol equivalents of the alcohol of the general formula R'-OH with one mol equivalent of the silane of the general formula III. For example, when n = 2, an organosilicon compound having an average composition according to the formula I may be produced by reacting four mol. equivalents of the alcohol of the general formula R'-OH with one mol equivalent of the silane of the general formula III. The mixture may be used as is or separated into individual compounds. When R' = R''3Si, the silane of the general formula III may be reacted with R''3Si-OH or with R''3Si-O-SiR''3. The compound R1 ''3Si-O-SiR' ' '3 can hydrolyse to yield R''3Si-OH and react with the silane of the general formula III. The reaction may be accelerated by neutral, acidic or basic catalysts, such as hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, para- toluenesulfonic acid, sodium hydroxide solution, potassium hydroxide solution, sodium methylate, sodium ethylate, Deloxan ASP 1/9, Amberlyst 15 ion exchange resins or metal compounds. Metal compounds may also be transition metal compounds. Metal compounds which may be used for the catalysts are metal chlorides, metal oxides, metal oxychlorides, metal alkoxides, metal oxyalkoxides, metal amides, metal imides or transition metal compounds with multiple, bound ligands. The following may, for example, be used as metal compounds: halides, amides or alkoxides main group 3 (M3+ = B, Al, Ga, In, Tl: M3+(OMe)3, M3+(OEt)3, M3+(OC3H7)3, M3+ (OC4H9) 3) , halides, oxides, imides, alkoxides, amides, thiolates and combinations of the stated classes of substituents with multiple, bound ligands on compounds of the lanthanide group (rare earths, atomic numbers 58 to 71 in the periodic system of elements), halides, oxides, imides, alkoxides, amides, thiolates and combinations of the stated classes of substituents with multiple, bound ligands on compounds of subgroup 3 (M3+ = Sc, Y, La: M3+(OMe)3, M3+(OEt)3, M3+(OC3H7)3, M3+(OC4H9)3, cpM3+(Cl)2, cp cpM3+(OMe)2, cpM3+(OEt)2, cpM3+(NMe2)2 where cp = cyclopentadienyl) , halides, amides, thiolates or alkoxides of main group 4 (M4+ = Si, Ge, Sn, Pb: M4+(OMe)4, M4+(OEt)4, M4+(OC3H7)4, M4+(OC4H9)4; M2+ = Sn, Pb: M2+(OMe)2, M2+(OEt)2, M2+(OC3H7)2, M2+(OC4H9)2, tin dilaurate, tin diacetate, Sn(OBu)2), halides, oxides, imides, alkoxides, amides, thiolates and combinations of the stated classes of substituents with multiple, bound ligands on compounds of subgroup 4 (M4+ = Ti, Zr, Hf: M4+(F)4, M4+(C1)4, M4+(Br)4, M4+(I)4; M4+(OMe)4, M4+(OEt)4, M4+(OC3H7)4, M4+(OC4H9)4, cp2Ti(Cl)2, cp2Zr(Cl)2 , cp2Hf(Cl)2, cp2Ti(OMe)2, cp2Zr(OMe)2, cp2Hf(OMe)2, cpTi(Cl)3, cpZr(Cl)3 , cpHf(Cl)3; cpTi(OMe}3, cpZr(OMe)3 , cpHf(OMe)3, M4+(NMe2)4, M4+(NEt2)4, M4+(NHC4H9) 4) , halides, oxides, imides, alkoxides, amides, thiolates and combinations of the stated classes of substituents with multiple, bound ligands on compounds of subgroup 5 (SM5+, M4+ or M3+ = V, Nb, Ta: M5+(OMe)5, M5+(OEt)5, M5+(OC3H7)5, M5+(OC4H9)5, M3+O(OMe)3, M3+O(OEt)3, M3+0 (OC3H7) 3, M3+0 (OC4H9) 3, cpV(OMe)4, cpNb(OMe)3 , cpTa(OMe)3; cpV(OMe)2, cpNb(OMe)3, cpTa(OMe)3), halides, oxides, imides, alkoxides, amides, thiolates and combinations of the stated classes of substituents with multiple, bound ligands on compounds of subgroup 6 (M6+, Mb+ or M4+ = Cr, Mo, W: M6+(OMe)6, M6+(OEt)6, M6+(OC3H7)6, M6+(OC4H9)6, M6+O(OMe)4, M6+O(OEt)4, M6+0 (OC3H7)4, M6+0 (OC4H9) 4, M6+O2(OMe)2, M6+O2(OEt)2, M6+O2 (OC3H7) 2, M6+O2 (OC4H9) 2, M6+O2(OSiMe3)2) or halides, oxides, imides, alkoxides, amides, thiolates and combinations of the stated classes of substituents with multiple, bound ligands on compounds of subgroup 7 (M7+, M6+, M5+ or M4+ = Mn, Re: M7+0 (OMe)5, M7+O(OEt)5, M7+0 (OC3H7)5, M7+O{OC4H9)5, M7+O2(OMe)3, M7+O2(OEt)3, M7+O2 (OC3H7) 3, M7+O2(OC4H9)3, M7+O2(OSiMe3)3, M7+O3 (OSiMe3) , M7+O3(CH3)). The metal compounds may have a free coordination site on the metal. Metal compounds which are formed by addition of water to yield hydrolysable metal compounds may also be used as catalysts. In one particular embodiment, titanates, such as for example tetra-n-butyl orthotitanate or tetra-iso-propyl orthotitanate, may be used as catalysts. The metal compounds may be anhydrous, as a result of which overall less water is introduced into the reaction mixture and fewer oligomeric silane compounds are obtained. The reaction may be performed at temperatures of between 20 and 200°C. In order to avoid condensation reactions, it may be advantageous to perform the reaction in an anhydrous atmosphere, preferably in an inert gas atmosphere. The organosilicon compounds according to the invention may be used as adhesion promoters between inorganic materials (for example glass fibres, metals, oxide fillers, silicas) and organic polymers {for example thermosets, thermoplastics, elastomers), or as crosslinking agents and surface-modifying agents. The organosilicon compounds according to the invention may be used as adhesion promoters in tyres filled with silica and/or starch. The present invention also provides rubber mixtures, which are characterised in that they contain rubber, filler, such as for example precipitated silica, optionally further rubber auxiliary substances, as well as at least one organosilicon compound according to the invention. The organosilicon compound according to the invention may be used in quantities of 0.1 to 20 wt.%, relative to the quantity of rubber used. The organosilicon compounds according to the invention and the fillers may preferably be added at composition temperatures of 100 to 200°C. They may, however, also be added later at lower temperatures (40 to 100°C), for example together with further rubber auxiliary substances. The organosilicon compound may be added to the mixing process both in pure form and applied onto an inert organic or inorganic support. Preferred support materials are silicas," waxes, thermoplastics, natural or synthetic silicates, aluminium oxide or carbon blacks. The following fillers may be used as fillers for the rubber mixtures according to the invention: carbon blacks: the carbon blacks to be used for this purpose are produced using the lamp black, furnace black or gas black processes and have BET surface areas of 20 to 200 m2/g, such as for example SAF, ISAF, HSAF, HAF, FEF or GPF blacks. The carbon blacks may optionally also contain heteroatoms such as for example Si. highly disperse silicas produced, for example, by precipitation of solutions of silicates or flame hydrolysis of silicon halides, with specific surface areas of 5 to 1000, preferably of 20 to 400 m2/g (BET surface area) and with primary particle sizes of 10 to 400 nm. The silicas may optionally also assume the form of mixed oxides with other metal oxides, such as Al, Mg, Ca, Ba, Zn and titanium oxides. synthetic silicates, such as aluminium silicate, alkaline earth metal silicates, such as magnesium silicate or calcium silicate, with BET surface areas of 20 to 400 m2/g and primary particle diameters of 10 to 4 00 nm. synthetic or natural aluminium oxides and hydroxides natural silicates, such as kaolin and other naturally occurring silicas. glass fibres and glass fibre products (mats, strands) or glass microbeads. Highly disperse silicas, produced by precipitation of solutions of silicates, with BET surface areas of 20 to 400 m2/g may preferably be used in quantities of 5 to 150 parts by weight, in each case relative to 100 parts of rubber. The stated fillers may be used individually or as a mixture. In a particularly preferred embodiment of the process, 10 to 150 parts by weight of light-coloured fillers, optionally together with 0 to 100 parts by weight of carbon black, and 0.3 to 10 parts by weight of a compound of the oligomeric organosilanes according to the invention, in each case relative to 100 parts by weight of rubber, may be used to produce the mixtures. Not only natural rubber but also synthetic rubbers are suitable for the production of the rubber mixtures according to the invention. Preferred synthetic rubbers are described, for example, in W. Hofmann, Kautschuk- technologie, Genter Verlag, Stuttgart 1980. They include, inter alia, polybutadiene (BR) polyisoprene (IR) styrene/butadiene copolymers with styrene contents of 1 to 60, preferably of 2 to 50 wt.% (SBR) isobutylene/isoprene copolymers (IIR) butadiene/acrylonitrile copolymers with acrylonitrile contents of 5 to 60, preferably of 10 to 50 wt.% (NBp.) partially hydrogenated or completely hydrogenated NBR rubber (HNBR) ethylene/propylene/diene copolymers (EPDM) as well as mixtures of these rubbers- Anionically polymerised S-SBR rubbers (solution SBR) with a glass transition temperature of above -50°C and the mixtures thereof with diene rubbers are in particular of interest for the production of automotive tyres. The rubber vulcanisates according to the invention may contain further rubber auxiliary substances, such as reaction accelerators, antioxidants, heat stabilisers, light stabilisers, antiozonants, processing auxiliaries, plasticisers, tackifiers, blowing agents, dyes, pigments, waxes, extenders, organic acids, retarders, metal oxides as well as activators, such as triethanolamine, polyethylene glycol, hexanetriol, which are known in the rubber industry. The rubber auxiliary substances may be used in known quantities which are determined, inter alia, by the intended application. Conventional quantities are for example quantities of 0.1 to 50 wt.%, relative to rubber. Sulfur or sulfur-donating substances may be used as vulcanising agents. The rubber mixtures according to the invention may furthermore contain vulcanisation accelerators. Examples of suitable vulcanisation accelerators are mercaptobenzothiazoles, sulfenamides, guanidines, thiurams, dithiocarbamates, thioureas and thiocarbonates. The vulcanisation accelerators and sulfur are used in quantities of 0.1 to 10 wt.%, preferably of 0.1 to 5 wt.%, relative to rubber. Vulcanisation of the rubber mixtures according to the invention may proceed at temperatures of 100 to 2000C, preferably of 130 to 180°C, optionally under a pressure of 10 to 200 bar. Blending of the rubbers with the filler, optionally rubber auxiliary substances and the organosilicon compound according to the invention may be performed in known mixing units, such as roll mills, internal mixers and compounding extruders. The rubber mixtures according to the invention are suited to the production of mouldings, for example for the production of pneumatic tyres, tyre treads, cable sheathing, hoses, drive belts, conveyor belts, roll covers, tyres, shoe soles, sealing rings and damping components. The organosilicon compounds according to the invention have the advantage that, at constant reactivity, less methanol or ethanol is released than with known silanes. Due to their inactivity, the nonvolatile alcohols are not separated from the silane or, due to their nonvolatility, remain in the polymer matrix. In either case, they are not released into the environment. Example 1: 200.0 g of bis(3-triethoxysilylpropyl)polysulfane (formula III where R = ethyl, R" = CH2CH2CH2, X = S, n = 2 and m = 3.8) and 70.0 g of 1-dodecanol (R1 = C12H25) are initially introduced at room temperature into a 1 litre four-necked flask with distillation attachment and combined with 1.0 g of Amberlyst 15. The yellowish solution is heated to 100- 130°C, the resultant ethanol removed by distillation and 210 g of 1-dodecanol are added dropwise within 1.5 h. The resultant ethanol is continuously removed by distillation. Towards the end of the reaction, the temperature is briefly raised to 150°C. The mixture is then distilled in a rotary evaporator under a vacuum at 80CC and 50 mbar. 408.5 g (99.4%) of a yellow liquid of the formula I where R = ethyl, R' = C12H25, R' = CH2CH2CH2, X = S, n - 2 and m = 3.8 are obtained. Example 2: 200.0 g of bis(3-triethoxysilylpropyl)polysulfane (formula III where R = ethyl, R" = CH2CH2CH2, X = S, n == 2 and m = 3.8) and 70.0 g of 1-dodecanol (R' = C12H25) are initially introduced at room temperature into a 1 litre four-necked flask with distillation attachment and combined with 0.7 g of p-toluenesulfonic acid monohydrate. The yellowish solution is heated to 100-105°C, the resultant ethanol removed by distillation and 210 g of 1-dodecanol are added dropwise within 1.5 h. The resultant ethanol is continuously removed by distillation. Towards the end of the reaction, the temperature is briefly raised to 130°C. The mixture is then distilled in a rotary evaporator under a vacuum at 80°C and 50 mbar. 389.1 g (94.7%) of a yellow liquid of the formula I where R = ethyl, R1 = C12H25, R" = CH2CH2CH2, X = S, n = 2 and m = 3.8 are obtained. Example 3: 200.0 g of bis(3-triethoxysilylpropyl)polysulfane (formula III where R = ethyl, R" = CH2CH2CH2, X = S, n = 2 and m = 3.8) and 60.6 g of diethylene glycol monobutyl ether (R' = (CH2) 2-O- (CH2) 2-O-C4H9) are initially introduced at room temperature into a 1 litre four-necked flask with distillation attachment and combined with 1.0 g of Amberlyst 15. The yellowish solution is heated to 115- 130°C, the resultant ethanol removed by distillation and 183.2 g of diethylene glycol monobutyl ether are added dropwise within 1.5 h. The resultant ethanol is continuously removed by distillation. The mixture is then distilled in a rotary evaporator under a vacuum at 80°C and 25 mbar. 367.2 g (98.2%) of a yellow liquid of the formula I where R = ethyl, R' = (CH2) 2-O-(CH2)2-O-C4H9, R" = CH2CH2CH2, X = S, n = 2 and m = 3.8 are obtained. Example 4: 200.0 g of bis(3-triethoxysilylpropyl)polysulfane (formula III where R = ethyl, R" = CH2CH2CH2, X = S, n = 2 and m = 3-8) and 60.9 g of diethylene glycol monobutyl ether (R1 = (CH2) 2-O- (CH2) 2-O-C4H9) are initially introduced at room temperature into a 1 litre four-necked flask with distillation attachment and combined with 0.7 g of p- toluenesulfonic acid monohydrate. The yellowish solution is heated to 120-130°C, the resultant ethanol removed by distillation and 182.8 g of diethylene glycol monobutyl ether are added dropwise within 1.5 h., The resultant ethanol is continuously removed by distillation. The mixture is then distilled in a rotary evaporator under a vacuum at 80°C and 20 mbar. 358.5 g (95.1%) of a yellow liquid of the formula I where R = ethyl, R1 = (CH2)2-O- (CH2)2-O-C4H9, R" = CH2CH2CH2, X = S, n = 2 and m = 3.8 are obtained. Example 5: 200.0 g of bis(3-triethoxysilylpropyl)polysulfane (formula III where R = ethyl, R" = CH2CH2CH2, X = S, n = 2 and m = 3.8) and 80.5 g of 1-tetradecanol (R1 = -C14H29) are initially introduced at room temperature into a 1 litre four-necked flask with distillation attachment and combined with 0.7 g of p-toluenesulfonic acid monohydrate. The yellowish solution is heated to 120-130°C, the resultant ethanol removed by distillation and 241.7 g of tetradecanol are added within 2 h. The resultant ethanol is continuously removed by distillation. The mixture is then distilled in a rotary evaporator under a vacuum at 80°C and 20 mbar. 432.1 g (95.4%) of a yellow liquid of the formula I where R = ethyl, R1 = C14H29, R1 ' = CH2CH2CH2, X = S, n = 2 and m = 3.8 are obtained. Example 6: 200.0 g of bis(3-triethoxysilylpropyl)polysulfane (formula III where R = ethyl, R" = CH2CH2CH2, X = S, n = 2 and m = 3.8) and 80.5 g of 1-tetradecanol (R1 = -C14H29) are initially introduced at room temperature into a 1 litre four-necked flask with distillation attachment and combined with 1.0 g of Deloxan ASP 1/9 from Degussa. The yellowish solution is heated to 120-130°C, the resultant ethanol removed by distillation and 241.7 g of tetradecanol are added within 2 h. The resultant ethanol is continuously removed by distillation. The mixture is then distilled in a rotary evaporator under a vacuum at 80°C and 20 mbar. 448.3 g (99.0%) of a yellow liquid of the formula I where R = ethyl, R1 = -C14H29, R" = CH2CH2CH2, X = S, n = 2 and m = 3.8 are obtained. Example 7: 200.0 g of bis(3-triethoxysilylpropyl)polysulfane (formula III where R = ethyl, R" = CH2CH2CH2, X = S, n = 2 and m = 3.8) and 50.4 g of diethylene glycol monoethyl ether (R1 = (CH2)2-O- (CH2)2-O-C2H5) are initially introduced at room temperature into a 1 litre four-necked flask with distillation attachment and combined with 0.7 g of p- toluenesulfonic acid monohydrate. The yellowish solution is heated to 125-130°C, the resultant ethanol removed by distillation and 151.2 g of diethylene glycol monoethyl ether are added dropwise within 1.5 h. The resultant ethanol is continuously removed by distillation. The mixture is then distilled in a rotary evaporator under a vacuum at 80°C and 25 mbar. 321.0 g (96.6%) of a yellow liquid of the formula I where R = ethyl, R1 = (CH2)2-O- (CH2)2-O-C2H5, R" = CH2CH2CH2/ X = S, n = 2 and m = 3.8 are obtained. Example 8: 200.0 g of bis(3-triethoxysilylpropyl)polysulfane (formula III where R = ethyl, R" = CH2CH2CH2, X = S, n = 2 and m = 3.8) and 50.4 g of diethylene glycol monoethyl ether (R' = (CH2) 2-O-(CH2) 2-O-C2H5) are initially introduced at room temperature into a 1 litre four-necked flask with distillation attachment and combined with 1.0 g of Amberlyst 15. The yellowish solution is heated to 125°C, the resultant ethanol removed by distillation and 151.2 g of diethylene glycol monoethyl ether are added dropwise within 1.5 h. The resultant ethanol is continuously removed by distillation. The mixture is then distilled in a rotary evaporator under a vacuum at 80°C and 25 mbar. 321.9 g (96.9%) of a yellow liquid of the formula I where R = ethyl, R' = (CH2) 2-0-(CH2) 2-O-C2H5, R" == CH2CH2CH2, X - S, n = 2 and m = 3.8 are obtained. Example 9: 200.0 g of bis(3-triethoxysilylpropyl)polysulfane (formula III where R = ethyl, R" = CH2CH2CH2, X = S, n = 2 and m = 3.8) and 71.8 g of diethylene glycol monohexyl ether (R' = (CH2)2-O-(CH2)2-O-C6H13) are initially introduced at room temperature into a 1 litre four-necked flask with distillation attachment and combined with 0.7 g of p- toluenesulfonic acid monohydrate. The yellowish solution is heated to 125°C, the resultant ethanol removed by distillation and 214.2 g of diethylene glycol monohexyl ether are added within 1.5 h. The resultant ethanol is continuously removed by distillation. The mixture is then distilled in a rotary evaporator under a vacuum at 80°C and 25 mbar. 414.4 g (99.4%) of a yellow liquid of the formula I where R = ethyl, R1 = (CH2) 2-O- (CH2) 2-O-C6H13, R" = CH2CH2CH2, X = S, n = 2 and m = 3.8 are obtained. Example 10: 125.2 g of 3-mercaptopropyltriethoxysilane (formula III where R = -CH2CH3, R" = -CH2CH2CH2-, X == -SH, n = 1, m = 1) and 22.5 g of 1-tetradecanol (R1 = -C14H29) are initially introduced at room temperature into a 1 litre four-necked flask with distillation attachment and combined with 1.0 g of p-toluenesulfonic acid monohydrate. The solution is heated to 120°C and, as soon as the resultant ethanol begins to distil off, 202.6 g of tetradecanol are added within 1.5 h. The resultant ethanol is continuously removed by distillation. The mixture is then distilled in a rotary evaporator under a vacuum at 80°C and 20 mbar. 298.8 g (98.9%) of a colourless liquid of the type I where R = -CH2CH3, R1 = -C14H29, R" = -CH2CH2CH2-, X = -SH, n = 1, m = 1 are obtained. Example 11: Testing of the organosilicon compounds in practical rubber- applications The formulation used for the rubber mixtures is stated in Table 1 below. The unit phr here means parts by weight relative to 100 parts of crude rubber used. The general method for the production of rubber mixtures and the vulcanisates thereof is described in the book "Rubber Technology Handbook", W. Hofmann, Hanser Verlag 1994. Polymer VSL 5025-1 is a solution-polymerised SBR copolymer from Bayer AG with a styrene content of 25 wt.% and a butadiene content of 75 wt.%. The copolymer contains 37.5 phr of oil and exhibits a Mooney viscosity (ML l+4/100°C) of 50 ± 4. Polymer Buna CB 24 is a cis-1,4-polybutadiene (neodymium type) from Bayer AG having a cis-1,4 content of at least 97% and a Mooney viscosity of 44 ± 5. Naftolen ZD from Chemetall is used as the aromatic oil. Vulkanox 4020 is 6PPD from Bayer AG and Protektor G35P is an antiozonant wax from HB-Fuller GmbH. Vulkacit D (DPG) and Vulkazit CZ (CBS) are commercial products of Bayer AG. Ultrasil 7000 GR is a readily dispersible precipitated silica from Degussa AG with a BET surface area of 170 m2/g. Si 69, bis(3- triethoxysilylpropyl)tetrasulfane, is a commercial product of Degussa AG. The rubber mixtures are produced in an internal mixer in accordance with the mixing instructions in Table 2. The results from technical rubber testing are shown in Table 4a and Table 4b. The mixtures are vulcanised for 20 min at 165°C. As is evident from the data in Tables 4a and 4b, the Mooney viscosity of the mixtures comprising the organosilicon compound according to the invention is below that of the reference mixture 1. The mixtures comprising the organosilicon compounds according to the invention (ethers) exhibit more rapid vulcanisation. The reinforcement factor is at a high level for all the mixtures, while tensile strength and elongation at break values are likewise comparable with the Si 69 reference. DIN abrasion is good for all the mixtures. The static rubber values demonstrate that the silica-silane-rubber bond has formed. The Goodrich Flexometer tests shows that the mixtures comprising the long-chain alcohols result in lower heat build-up and an improved permanent set. MTS testing clearly reveals lower dynamic rigidity values and a reduced tan 5 60°C (lower rolling resistance). Example 12: 180.0 g of bis(3-triethoxysilylpropyl)disulfane (formula III where R = Ethyl, R" = CH2CH2CH2, X = S, n = 2 and m = 2.2) and 80.5 g of 1-tetradecanol (R' = -C14H29) are initially introduced at room temperature into a 1 litre four-necked flask with distillation attachment and combined with 0.7 g of p-toluenesulfonic acid monohydrate. The yellowish solution is heated to 120-130°C, the resultant ethanol removed by distillation and 237.5 g of tetradecanol are added within 2 h. The resultant ethanol is continuously removed by distillation. The mixture is then distilled in a rotary evaporator under a vacuum at 80°C and 20 mbar. 418.5 g (98.0%) of a yellow liquid of the formula I where R = ethyl, R1 = -C14H29, R1 ' = CH2CH2CH2, X = S, n = 2 and m = 2.2 are obtained. Example 13: A mixture of 125.2 g of 3-mercaptopropyltriethoxysilane (formula III where R = -CH2CH3, R" = -CH2CH2CH2~, X = -SH, n = 1, m = 1), 225.1 g of 1-tetradecanol (R' = -C14H29) and 1.0 g of p-toluenesulfonic acid monohydrate are heated to 110°C in the 1 litre flask on a rotary evaporator and the resultant ethanol removed by vacuum distillation at 40 mbar within 4 h. 298.5 g (98.8%) of a colourless liquid of the formula I where R = -CH2CH3, R1 = -C14H29, R" = -CH2CH2CH2-, X = -SH, n = 1, m = 1 are obtained. Example 14: A mixture of 200.0 g of bis (3- triethoxysilylpropyDpolysulfane (formula III where R = ethyl, R" = CH2CH2CH2, X = S, n = 2, m = 3.8), 322.2 g of 1-tetradecanol (R' = -C14H29) and 1.0 g of p- toluenesulfonic acid monohydrate are heated to 110°C in the 1 litre flask on a rotary evaporator and the resultant ethanol removed by vacuum distillation at 40 mbar within 4 h. 448.1 g (99.0%) of a yellow liquid of the formula I where R = ethyl, R' = -C14H29, R1 ' = CH2CH2CH2, X = S, n = 2 and m = 3.8 are obtained. Example 15: A mixture consisting of 150 g of Si 69 (compound III where R = -CH2CH3, R2 = -CH2CH2CH2-, X = S, n = 2, m = 1 to 10 and an average m of 3.8), and a 4x molar quantity of tetradecanol are heated with the stated quantities of catalyst to the stated temperatures in the 1 litre flask on a rotary evaporator and the resultant ethanol is removed by vacuum distillation at 40 mbar within 120 min (Table 5). After cooling, a yellow to yellow- orange, relatively high viscosity liquid of the formula I where R = -CH2CH3, R2 = -CH2CH2CH2-, X = S with n = 2 and m = 1 to 10 is obtained. Si 69 is bis(3-triethoxysilylpropyl)polysulfane with an average sulfane chain length of 3.8 from Degussa AG. Ti(OC2H5)4, Ti(OC3H7)4 and Ti (OC4H9) 4 are produced by Aldrich. p-Toluenesulfonic acid and p-toluenesulfonic acid sodium salt are produced by Merck-Schuchardt. Example 16: A mixture consisting of 100 g of Si 69 (compound III where R = -CH2CH3, R2 = -CH2CH2CH2-, X = S, n = 2, m = 1 to 10 and an average m of 3.8), and a 4x molar quantity of corresponding alcohol are heated with the stated quantities of catalyst to 130°C in a 500 ml three- necked flask and the resultant ethanol is removed by distillation within 120 min (Table 6). After cooling, a yellow to yellow-orange, relatively high viscosity liquid of the formula I where R = -CH2CH3, R2 = -CH2CH2CH2-, X = S with n = 2 and m = 1 to 10 is obtained. Tables 5 and 6 show the corresponding NMR analytical results The nuclear magnetic resonance analysis results are obtained using a Bruker DRX 500 NMR spectrometer in accordance with the rules and operating procedures known to the person skilled in the art. The mass frequencies used are 99.35 MHz for 29Si nuclei and 500 MHz for 1H nuclei. Tetramethylsilane (TMS) is used as reference in each case. Conversion is defined as the quotient obtained from the 1H NMR integral (Si-O-CxHy) divided by the sum of the 1H NMR integral (Si-O-Et) and XH NMR integral (Si-O-CxHy) x 0.66. Conversion is stated as a percentage of 1. 100% conversion means that 4 of 6 equivalents of EtO have been replaced and 2 equivalents of EtO remain on the silicon. The quantity of oligomers is determined by 29Si NMR by comparing the integrals of the Si(OEt)3 and the Si(OEt)2-O-Si(OEt)2 signals. At a comparable or even lower molar catalyst concentration, the transesterification conversion of the process according to the invention using metal compounds is higher at lower temperatures than when other catalysts are used. In addition, the quantity of oligomers formed is lower. If p-toluenesulfonic acid sodium salt is used as an anhydrous equivalent of p- toluenesulfonic acid monohydrate, conversion is found to be poorer, even when large quantities of catalyst are used, than when titanium alkoxides are used (Table 6) . 1. Organosilicon compounds of the general formula I and/or II wherein R is ethyl group, R' is identical or different and is a C9-C30 branched or unbranched monovalent alkyl or alkenyl group, branched or unbranched C2-C30 alkyl ether group, branched or unbranched C2-C30 polyether group, where R'" is C1-C30 branched or unbranched alkyl or alkenyl group, aralkyl group or aryl group, R" is a branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic divalent C1-C30 hydrocarbon group,00 X is O(C=O)-R'" where n = 1 and m = 1, SH where n = 1 and m =1, S hwere n = 2 an dm =1-10 and mixtures thereof, S(C=O)-R'' where n = 1 and m = 1 where n = 1 and m = 1. 2. Organosilicon compounds as claimed in claim 1, wherein R" means CH2, CH2CH2, CH2CH2CH2, CH2CH2CH2CH2, CH(CH3), CH2CH(CH3), C(CH3)2, CH(C2H5), CH2CH2CH(CH3), CH2CH(CH3)CH2 or 3. A process for the production of the organosilicon compounds of the invention as claimed in claim 1, wherein silanes of the general formula III in which R, R", x, m an d n have the above-stated meaning, are reacted with alcohols of the general formula R'-OH, in which R' exhibits the above-stated meaning, with elimination of R-OH, and R-OH is continuously separated from the reaction mixture by distillation. 4. A process as claimed in claim 3, wherein hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, para- toluenesulfonic acid, sodium hydroxide solution, potassium hydroxide solution, sodium methylate, sodium ethylate, Deloxan ASP 1/9, Amberlyst 15 ion exchange resins are used as catalyst. 5. A process as claimed in claim 3, wherein metal compounds are used as catalyst. 6. A process as claimed in claim 3, wherein the reaction is performed at temperatures of between 20 and 200°C. 7. A process as claimed in claim 3, wherein the reaction is performed in an anhydrous, inert gas atmosphere. 8. Rubber mixtures wherein they contain rubber, filler, optionally further rubber auxiliary substances, as well as at least one organosilicon compound of the invention as claimed in claim 1. Organosilicon compounds Organosilicon compounds of the general formula I and/or 5 II are produced by reacting silanes of the general formula 10 III with alcohols of the general formula R'-OH, with elimination of R-OH, and R-OH is continuously separated from the reaction mixture by distillation. 15 The organosilicon compounds may be used in rubber mixtures.

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