DE3025034A1 - SILANES AND METHOD FOR THEIR PRODUCTION - Google Patents

Description

PATENT ADVOCATE DR. RICHARD KNEISSL Widenmayerstr. 46

D-8000 MUNICH Tel 089 / 2951.25

-.fr- Munich, June 2, MT 17a-Dr.K / Da

M&T Chemicals Inc. Stamford, Ct./V.St.A.

Silanes and process for their preparation

130009/0688

description

In the German patent application P 29 15 072 are phenoxyalkyl, thiophenoxyalkyl and pyridyloxyalkylsilanes and a method described for the production of the same. They are suitable as coupling agents for glass fiber reinforced composites, flocculants for water purification and for sizing glass fibers or fabrics.

It has now been found that a number of other similar such silanes are particularly suitable for this and similar purposes.

The invention therefore relates to new silanes of the general formula

where R is alkenyl with 2-5 carbon atoms,

-NH ,, -NR ⁸ H, -NB? ,, -n

v / Z »-CHO, -CN, I Γ -

-COR, -COOR , Cl, Br, j,

-SO ₂ R, -SOR ⁸ or -NO ₂ ; R ^{2 represents} alkyl, alkoxy or thioalkoxy and has 1 to 12 carbon atoms; R ³ for Cl, Br, ^{I ', -COOR 8} , -CN, -NH ₂ , -NR ⁸ H, -NR ⁸ ,

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or-NC. stands;

R ^{4 represents} alkyl of 1 to 12 carbon atoms; R represents methylene or alkylene having 3 to 12 carbon atoms; R and R each independently represent alkyl, cyanoalkyl, alkenyl, cycloalkyl, aryl, alkaryl or aralkyl, each alkyl group, whether it is completely or only partially

6 7
represented by R and R have 1 to 12 carbon atoms

having; R is alkyl, cycloalkyl, aryl, alkaryl, or aralkyl, each alkyl group having 1 to 12 carbon atoms having;

PP

ür— f C—, -CH-CH-,

Λ for VV »-ν, η-ν, β-, ι s ι _or

R ^ia R "■

stands, where R and R independently of one another are water.

substance, chlorine, bromine, iodine or alkyl with 1 to 12 carbon

12 14

atoms stand; R and R independently of one another represent hydrogen or alkyl having 1 to 12 carbon atoms;

Ϊ ■? Z is oxygen, sulfur, -S- or -S-.; m for a

Is an integer from 1 to 5; η stands for 0, 1 or 2; ρ for or 3; q is 1, 2 or 3; and t is 0 or 1; with the caveat that

a) .. if m stands for 2, one of the or both symbols R for -NH ₀ , -NR H, -NR ₀ ,

■ SOR

R ¹⁰

; or j-COOR * - stand and. given-

if a remaining symbol R stands for -CN, Cl, Br, J or -NO,

stands;

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1 8

b) if m stands for 3 , one of the symbols R for -NH ₃ , -NR H,

and the other two

Symbols R ¹ stand for chlorine, bromine or iodine;

c) when m is 4 or 5, R ^{1 is} chlorine, bromine or iodine;

d) η is 1 or 2 when m is 1 and R ^{1 is} -NH ₂ or

-NO ₂ ; and

e) the sum of m and η is equal to or less than 5.

The new silanes can be prepared by essentially having practically equimolar amounts of alkali metal or Alkaline earth metal compound of the general formula

S ^ 1

with a

Haloalkylsilane of the general formula

P.

R ^r

"-P: I '

wherein M stands for an alkali metal or an alkaline earth metal and X stands for chlorine, bromine or iodine, reacted with one another by reacting the alkali metal or alkaline earth metal compound and the silane under practically anhydrous conditions at temperatures between room temperature and 200 ° C in a liquid reaction medium which consists at least partially of at least one dipolar aprotic liquid and optionally otherwise of a liquid hydrocarbon boiling between 40 and 200 ° C., causing the reaction medium to be practically complete via a

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Conversion of the alkali metal or alkaline earth metal compound and the silane into the desired functional phenoxyalkyl, thiophenoxyalkyl or pyridyloxyalkylsilane holds a temperature of 40 to 200 ° C for a sufficient period of time, the reaction medium is filtered to isolate the desired silane and the liquid reaction medium evaporates from the liquid phase .

The new compounds are functionally substituted phenoxy, thiophenoxy, pyridyloxy and thiopyridyloxyalkylsilanes. the functional substituents on the phenyl group, which is represented by R in the general formula, can be selected from

Il
-NH ₂ , -NR ⁸ H, -NR ₂ , -N <^ "*> R% -CHO, -CN, -COR *, -COOR ⁸ ,

• I

Cl, Br, *, -N <_, -N < _ie , -N < _ia , -SO ₂ R

-SOR and -NO "exist. Amino groups are preferred substituents, since the resulting compounds have many useful applications. The substituents can be ortho-, meta- or para position with respect to the oxygen or sulfur atom, represented by Z in the above formula. The phenoxy, thiophenoxy, pyridyloxy or thiopyridyloxy group is bonded to the silicon atom through an alkylene group selected from a methylene group or a higher alkylene group with 3 to 12 carbon atoms, the latter can be either linear or branched. Compounds in which R is ethylene, in the presence of traces of aqueous Acids or bases have been found to be so unstable that they cannot be used for practical purposes. In addition to the alkylene group mentioned the silicon atom is also on three alkoxide or aryloxide groups, which are represented by OR in the above formula, or to two alkoxide or aryloxide groups and a hydrocarbon

1 30009/0688

bonded substance or cyanoalkyl group. The term "hydrocarbon" includes alkyl, cycloalkyl, aryl, alkaryl and aralkyl,

6 7
as defined above for R and R.

The present compounds are expediently prepared by that one has an alkali metal or alkaline earth metal salt, preferably the sodium or potassium salt, of the desired phenol, thiophenol, hydroxypyridines or thiopyridines with a haloalkylsilane the general formula

XR ⁵ Si '

implements. This reaction is highly exothermic and is preferably carried out in an inert atmosphere and in the absence of even Traces of water run, as water is known to easily mix with silanes that have 2 or 3 alkoxy or aryloxy groups, that are bonded to silicon react to form polymeric products. The reaction medium is a dipolar, aprotic one Liquid such as dimethyl sulfoxide, N, N-dimethylformamide, Tetramethylurea, N-methylpyrolidone or hexamethylphosphoramide. The dipolar aprotic liquid makes up 1 to 100% by weight of the reaction medium and preferably 20 to 50% by weight of the reaction medium. The remainder of the reaction medium consists essentially of at least one liquid hydrocarbon, which boils at 40 to about 200 C under atmospheric pressure. The purpose of the liquid hydrocarbon consists in facilitating the removal of any water present in the reaction mixture by azeotropic distillation. Preferably, the haloalkylsilane gradually becomes the reaction mixture containing the alkali metal or alkaline earth metal salt contains, added. After the addition has ended and the exothermic reaction has subsided, it is usually desirable that Heat the reaction mixture to about 70 to 150 ° C. for several hours in order to achieve practically complete conversion of the Reactants in the desired functionally substituted phenoxyalkyl, thiophenoxyalkyl, thiopyridyloxyalkyl or Ensure pyridyloxyalkylsilane. The present compounds, many of which are colorless, are high-boiling

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viscous oils, are soluble in the reaction medium and can easily be removed by removing the above-mentioned liquid hydrocarbon and the above-mentioned dipolar liquid. Some of the connections will go dark after long periods of time exposed to light.

The for the preparation of the compounds according to the invention as Starting materials required tri (hydrocarbonoxy) haloalkylsilanes or di (hydrocarbyl oxy) haloalkylsilanes either commercially available compounds or can easily be prepared by adding the corresponding haloalkyltrihalosilane or a silane of the formula

1 C ^^ " · 3 ~ Ρ η Λ

X R Si ^, where X and X are chlorine, bromine or

Stand iodine, with an alcohol R OH, which has 1 to 12 carbon atoms has, implements. Alternatively, the hydroxyl group can be attached to a carbocyclic or heterocyclic ring structure such as an a cyclohexyl or phenyl group. The haloalkyltrihalosilane can be prepared by using a haloalkene, such as allyl chloride or methallyl chloride,

with a trihalosilane, HSiX ₃ , at room temperature in the presence of a platinum catalyst. Methods for making the intermediate silanes are well known in the art. A detailed discussion of the reaction conditions for this is therefore not necessary in the present description.

Examples of preferred functionally substituted phenols and thiophenols which are used to prepare the compounds according to the invention Can be used are aminophenols, aminothiophenols and aminochlorophenols, wherein the amino group is in is in the ortho, metha or para position to the hydroxyl group, the isomeric hydroxybenzaldehydes and the isomeric esters of hydroxybenzoic acid and mercaptobenzoic acid, with the alcohol residue of the ester has 1 to 12 carbon atoms. If the alcohol contains a phenyl group, then the number is the Carbon atoms 7 to 18. Other functional substituents, the

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may be present on the phenyl group, result from the the above definition of the invention and the preceding claims. In addition, the phenyl group can be 1 or 2 alkyl, Contain cycloalkyl or aryl groups.

Alternatively, the amino group can be an aminophenol or aminothiophenol be reacted beforehand to form an amide, imide, carbamate, sulfonamide or other group, namely before the reaction of the phenol or thiophenol in the form of its alkali metal or alkaline earth metal salt with the hydroxyalkylalkoxysilane.

An anhydrous form of the alkali metal or alkaline earth metal salt of phenol, thiophenol, hydroxypyridines or mercaptopyridines can be prepared by using the free metal or a hydride or an alkoxide of the metal such as sodium hydride or sodium methoxide. All of these compounds are added to a solution of the desired phenol, thiophenol or pyridine derivative in a dipolar aprotic solvent, which optionally contains a liquid hydrocarbon. The metal, metal hydride or metal alkoxide is conveniently used as a dispersion or a slurry in a liquid hydrocarbon. The temperature of the reaction medium is kept between room temperature and approximately 50 ^° C. in order to avoid an uncontrolled exothermic reaction.

The functionally substituted silanes of the invention are useful as coupling agents for joining an organic polymer with an inorganic material, such as glass fiber or metal, as a flocculant for purifying water, as a sizing Preparations for glass fibers or fabrics and as components for polishes and waxes, in particular for automobiles. By implementing of the compounds according to the invention with liquid hydroxyl- or alkoxyl-terminated organopolysiloxanes, optionally together With fillers, elastomeric products can be formed, which can be used as coating materials, sealants and molding compounds are suitable. Compounds in which the substituent R der

4 above formula consists of amino or dialkylamino (-NH "or -NR ₂ ), waxes and polishes give detergent resistance.

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The invention is illustrated in more detail by means of the following examples. All parts and percentages contained therein are based on weight, unless otherwise stated. '■

EXAMPLE 1 ■

3- (p-aminophenoxy) propyltrimethoxysilane

A glass reactor is charged with 60 g (0.55 mol) of p-aminophenol, 43.28 g of a 50% strength aqueous solution of sodium hydroxide (0.54 mol NaOH), 112 ml of dimethyl sulfoxide and 120 ml of toluene. The reaction mixture obtained is then heated to boiling for 6 hours under a nitrogen atmosphere in order to remove all of the water present by azeotropic distillation. The reaction mixture is then allowed to cool to about 75 ° C. at which point 109 g (0.55 mol) of 3-chloropropyltrimethoxysilane are added dropwise with stirring. During this addition, the temperature of the reaction mixture rises spontaneously to 85 ° C. The temperature of the reaction mixture is kept at 75 to 85 ° C. by heating and appropriate control of the rate of addition. When the addition is complete, the reaction mixture is heated to 115 ° C. for 16 hours, whereupon it is allowed to cool and filtered to remove any solid material that may be present. The solvents are then removed under a pressure of about 15 mm Hg at a temperature of about 60 ° C. The pressure is then reduced to 3 to 4 mm Hg and the material which boils at 170 to 180 ° C. is recovered. This fraction, which weighs 70 g, is then distilled in a fractionating column, collecting 50 g of a distillate which boils at 175 to 177 ° C. at a pressure of 3 mm Hg. The colorless liquid obtained in this way contains 10.19% silicon and 5.20% nitrogen. The calculated values for 3- (p-aminophenoxy) propyltrimethoxysilane are 10.33% silicon and 5.17% nitrogen. The IR and NMR spectra of the product are consistent with the proposed structure .

130Q09 / 0688

EXAMPLE 2 Preparation of 3- (m-aminophenoxy) propyltrimethoxysilane

The general procedure described in Example 1 is repeated by placing an appropriate reaction vessel with 300 g (2.75 moles) of m-aminophenol, 560 ml of dimethyl sulfoxide, 600 ml of toluene and 216 ml of a 50% aqueous solution of sodium hydroxide (2.70 Mol NaOH) charged. The water present in the reaction vessel is removed by azeotropic distillation under a nitrogen atmosphere at a temperature of 120.degree. The temperature of the reaction mixture is then lowered to 90 ° C. and maintained approximately at this value with the gradual addition of 545 g (2.75 mol) of 3-chloropropyltrimethoxysilane. When the addition has ended, which takes 2 hours, the reaction mixture is heated to boiling temperature for 16 hours. The product obtained is then obtained as described in Example 1 and fractionally distilled. The fraction boiling at 178 to 180 ° C under 3 mm Hg pressure is collected to give 630 g (85% yield) of material. The IR and NMR spectra of the product obtained confirm the proposed structure of the formula:

OCH ₂ CH ₂ CH ₂ Si (OCH ₉ )

A vapor phase chromatogram of the product obtained shows a purity of over 98%.

EXAMPLE 3 Production of 3- (p-Formy! Phenoxy) propy1trimethoxysilane

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The general procedure described in Example 1 is repeated using an appropriate reaction vessel with 62.2 g (0.55 mol) of p-hydroxybenzaldehyde, 112 ml of dimethyl sulfoxide, 120 ml of toluene and 43.2 g of a 50% strength aqueous sodium hydroxide solution containing 0.54 mol of NaOH are charged. By azeotropic distillation at one temperature from about 110 to 115 ° C remove all of the existing Water. The reaction mixture is heated to boiling temperature, gradually adding 109 g (0.55 mol) of 3-chloropropyltrimethoxysilane admits. To isolate the 3- (p-formylphenoxy) propyltrimethoxysilane obtained as product the reaction mixture is removed, the solvents are removed from the resulting liquid phase under reduced pressure and subjected the accumulated solids of a fractional distillation. The one boiling at 208 ° C and a pressure of 3 mm Hg The fraction is collected (based on the silane, the product yield is 85%). The IR and NMR spectra of the obtained product confirm the proposed structure of the formula!

OCH

The vapor phase chromatogram of the product indicates a purity of over 98%.

EXAMPLE 4

Preparation of 3- (m-diethylaminophenoxy) propyltrintethoxysilane

The general procedure described in Example 1 is repeated, and a corresponding reaction vessel is filled with 90.75 g (0.55 mol) of m-diethylaminophenol, 112 ml of dimethyl sulfoxide, 120 ml of toluene and 43.28 g of a 50% strength aqueous sodium hydroxide solution loaded. By azeotropic distillation becomes

130009/0688

all of the water present in the reaction vessel is removed. Then allowed the reaction mixture to 8O ⁰ C to cool, and at this time are added over a Zeit.dauer of 2-r st.all gradually 109 g (0.55 mol) chloropropyltrimethoxysilane. During the addition the temperature of the reaction mixture to increase 88 ⁰ C. After completion of the addition keeps the temperature of the reaction mixture by appropriate heating 16 st to 8O ⁰ C. then allowed to the reaction rate 'cool mixture and is filtered subsequently. The resulting liquid phase is evaporated under a pressure of 5 mm Hg to remove toluene and dimethyl sulfoxide. The pressure in the reaction vessel is then reduced to 2 mm Hg, and the 3- (m-diethylaminophenoxy) propyltrimethoxysilane obtained as the product is collected at a temperature of 185-187 ° C. A corresponding vapor phase chromatogram. shows that the product obtained is 97 % pure.

EXAMPLE 5 Preparation of 3- (3-pyridyloxy) propyltrimethoxysilane

The general procedure described in Example 1 is repeated, charging an appropriate reaction vessel with 52.3 g (0.55 mol) of 3-hydroxypyridine, 112 ml of dimethyl sulfoxide, 120 ml of toluene and 43.2 g of a 50% aqueous sodium hydroxide solution. The water present in the reaction vessel is removed by azeotropic distillation over a period of 64 hours. The temperature of the reaction mixture is maintained at 85 to 105 ° C. during this time. The reaction mixture is then kept at a temperature of 95 ° C. and 109 g of 3-chloropropyltrimethoxysilane are gradually added. This temperature is maintained for 7 hours, whereupon a corresponding vapor phase chromatogram of the reaction mixture shows that the reaction has practically ended. The reaction mixture is filtered and the diluents present

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(Toluene and dimethyl sulfoxide) are evaporated at a pressure of 5 mm Hg. The 3- (3-pyridyloxy) propyltrimethoxysilane obtained as product is collected at a temperature of 142 ° C. under a pressure of 1 mm Hg. A corresponding vapor phase chromatogram shows that this product has a purity of 97%.

Example 6 Production of m-aminophenoxypropyl-methyldimethoxysilane

Using the procedure described in Example 1, a reactor containing 60 grams (0.55 moles) of p-aminophenol, 43.28 grams a 50% (weight) aqueous solution of sodium hydro-

xide (0.54 mol NaOH) 112 ml of dimethyl sulfoxide and 120 ml of toluene were charged. The resulting mixture was heated to boiling for 6 hours under a nitrogen atmosphere in order to remove all of the water by azeotropic distillation. The reaction mixture was then allowed to cool to about 75 ° C, whereupon 100.4 g (0.56 mol) of 3-chloropropyl-methyldimethoxysilane was added dropwise while stirring the reaction mixture. After the reaction had ended, the reaction mixture was heated to 115 ° C. for 16 hours, whereupon the mixture was allowed to cool and filtered to remove solid material. The solvents were then removed under a pressure of approximately 15 mm Hg at a temperature of approximately 60 ^° C. The pressure was then reduced to 3-4 mm Hg and the material boiling at 230-235 ° C was recovered. This fraction weighed 112 g, which corresponds to a yield of 80% based on the starting materials. Analysis by gas phase chromatography showed that the purity of the product was greater than 98%. The infrared and nuclear magnetic resonance spectrum of the product were consistent with the proposed structure. ,. ·

130009/0688

Example 7

Production of 3,5-bis (carbomethoxv) phenoxypropyl-trimethoxysilane

Using the procedure of Example 1, a reactor was charged with 115.5 g (0.55 moles) of 3,5-bis (carbomethoxy) phenol, 43.28 g of a 50% strength (by weight) aqueous solution of sodium hydroxide (corresponding to 0.54 mol of NaOH), 112 ml of dimethyl sulfoxide and charged 120 ml of toluene. The resulting reaction mixture boiled under a nitrogen atmosphere for 6 hours heated to remove substantially all of the water by azeotropic distillation. The reaction mixture was then Allowed to cool to about 75 ° C, whereupon 109 g (0.555 mol) of chloropropyl-trimethoxysilane dropwise to the reaction mixture were admitted. After the addition was complete, the temperature of the reaction mixture was raised to 115 ° C and approx Maintained at this value for 16 h, after which the reaction mixture was allowed to cool to room temperature. The reaction mixture was then filtered, and the toluene, dimethyl sulfoxide and other volatile materials were removed under aspirator vacuum. The liquid residue was then under a Distilled pressure of 3 to 4 mm Hg, and the fraction boiling between 240 and 270 ° C was collected and weighed. she weighed 95 g. Fractional distillation of this material gave 75 g of a viscous colorless oil which, under a pressure of 3 mm Hg in a boiling range of 250 to 252 ° C was collected. The infrared and nuclear magnetic resonance spectrum of the product agreed with the proposed structure. The gas phase chromatogram showed that the product had a purity of 98% exhibited. The product gradually solidified on standing.

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Example 8

Production of o-propenylphenoxypropyl-trimethoxysilane

Using the general procedure described in Example 1, a reactor containing 73.7 grams (0.55 moles) of o-allyl phenol, 43.28 g of a 50% (weight) aqueous solution of sodium hydroxide (0.54 mol NaOH), 112 ml of dimethyl sulfoxide and 120 ml of toluene charged. The resulting mixture was heated to boiling point under a nitrogen atmosphere for 6 hours. to remove all water by azeotropic distillation. The reaction mixture was then allowed to cool to approximately 75 ° C left, whereupon 109 g (0.56 mol) of 3-chloropropyl-trimethoxysilane were added dropwise while the reaction mixture was stirred. When the addition was complete, the reaction mixture became Heated at 115 ° C for 16 h, then allowed to cool and filtered to remove solid material. The solvents were then subjected to a pressure of approximately 15 mm Hg at a temperature of approximately 60 ° C removed. The pressure was then reduced to 2mm Hg and the material boiling at 146 ° C was collected. The weight this fraction corresponded to a yield of 90%, based on the starting materials. Analysis by gas phase chromatography showed that the purity of the product was greater than 98%. The infrared and nuclear magnetic resonance spectrum of the product were correct consistent with the proposed structure.

Example 9

Preparation of m-aminophenoxy-2-methylpropyl-methyldimethoxysila-n

Using the procedure described in Example 1 a reactor was filled with 60 g (0.55 mol) of p-aminophenol, 43.28 g of a 50% (weight) aqueous solution of sodium hydroxide (0.54 mol NaOH), 112 ml dimethyl sulfoxide and 120 ml toluene. The resulting mixture was 6 h under a stick

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The substance atmosphere is heated to the boiling point in order to remove all of the water present by azeotropic distillation. The reaction mixture was then allowed to cool to approximately 75 ° C, whereupon 117 g (0.56 mol) of 2-methylchloropropyl-methyldimethoxysilane was added dropwise while the reaction mixture was stirred. When the addition was complete, the reaction mixture was heated to 115 ° C for approximately 16 hours and then allowed to cool and. was filtered to remove all solid material. The solvents were removed under a pressure of approximately 15 mm Hg at a temperature of approximately 60 ^° C. The pressure was then reduced to 2 mm Hg and the material boiling at 165 ° C was collected. Analysis by gas phase chromatography showed the purity of the product to be greater than 98 % . The product was a pale yellow viscous liquid.

Example 10

Production of p-carbomethoxyphenoxypropyl-methyldimethoxysilane

Using the procedure described in Example, a reactor with 83.7 g (0.55 mol) of methyl p-hydroxybenzoate, 43.28 g of a 50% strength (by weight) aqueous solution of sodium hydroxide (0.54 mol NaOH), 112 ml dimethyl sulfoxide and 120 ml Toluene charged. The resulting mixture was heated to the boiling point under a nitrogen atmosphere for 6 hours to obtain the remove all water present by azeotropic distillation. The reaction mixture was then allowed to cool to approximately 75 ° C left, whereupon 109 g (0.56 mol) of 3-chloropropyl-trimethoxysilane were added dropwise while the reaction mixture was stirred. When the addition was complete the reaction mixture was heated to 115 C for approximately 16 hours, then the mixture was allowed to cool and filtered to remove solids to remove. The solvents were then subjected to a pressure of approximately 15 mm Hg at a temperature of approximately 60 ° C removed. The pressure was then reduced to 2mm Hg and the material boiling at 230-235 ° C was collected. The weight this fraction corresponded to a yield of 92%, based on

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on the raw materials. Analysis by gas phase chromatography showed that the purity of the product was greater than 98%. The infrared and nuclear magnetic resonance spectrum of the product agreed with the proposed structure.

Example 11

Preparation of m-succinimidophenoxvpropyl-trimethoxysilane A solution containing 200 g of succinic anhydride, 218 g of m-aminophenol and 1 liter of glacial acetic acid was heated to boiling point for 16 h in a reactor equipped with a mechanically driven stirrer and a water-cooled reflux condenser. The reaction mixture solidified on cooling to room temperature. The solid was pulverized, washed with water to remove acid and then dried. The m-succinimidophenol obtained (105.1 g, 0.55 mol) was introduced together with 43.28 g of a 50% strength (by weight) aqueous sodium hydroxide solution, 112 ml of dimethyl sulfoxide and 120 ml of toluene into a reactor equipped with a nitrogen inlet tube a water-cooled reflux condenser and a Dean-Stark trap. The resulting mixture was heated to boiling point under a nitrogen atmosphere for 6 hours to remove all water present by azeotropic distillation. The reaction mixture was then allowed to cool to about 75 ° C. at which point 109 g (0.56 mol) of 3-chloropropyl-trimethoxysilane was added dropwise while the reaction mixture was stirred. After the addition was complete, the reaction mixture was heated to 115 ° C for approximately 16 hours, after which the mixture was allowed to cool and filtered to remove solid material. The solvents were then removed under a pressure of about 15 mm Hg at a temperature of about 60 ° C. The pressure was then reduced to 0.5 mm Hg and the material boiling at 228 ° C was collected. Analysis by gas phase chromatography showed that the purity of the product, which consisted of a white solid, was greater than 98%. The infrared and nuclear magnetic resonance spectrum of the product were consistent with the proposed structure.

130009/0 6 88

Claims (14)

Claims where R is alkenyl with 2-5 carbon atoms, -NHa, -NR ⁸ H, -NR ³ ,, -N ^ Jl *, -CHO, -CN, ^ a -COR *, -COOR, Cl, Br, j, " ^N C _x0 ". -SO ₉ R ⁸ , -SOR ⁸ or -NO ₀ ; R ² for alkyl, alkoxy or thio 3 is alkoxy and has 1 to 12 carbon atoms; R for Cl, Br, J, -COOR ⁸ , -CN, -NH ₂ , -NR ⁸ H, -NR ⁸ , © which stands -N \; R represents alkyl of 1 to 12 carbon atoms; R represents methylene or alkylene having 3 to 12 carbon atoms; R and R each independently represent alkyl, cyanoalkyl, alkenyl, cycloalkyl, aryl, alkaryl or aralkyl, each alkyl group, whether it is completely or only partially 130009/0688 302503 ^ 6 7 represented by R and R have 1 to 12 carbon atoms having; R for alkyl, cycloalkyl, aryl, alkaryl or aralkyl wherein each alkyl group has 1 to 12 carbon atoms; R ¹¹ R ^1S ^ V ^ R ⁹ for 9 9 »-CH-CH-, ~ fs I or R ¹² R ¹ * '"\ / stands, where R and R independently of one another represent hydrogen, chlorine, bromine, iodine or alkyl with 1 to 12 carbon 12 14 atoms stand; R and R independently of one another represent hydrogen or alkyl having 1 to 12 carbon atoms; Z represents oxygen, sulfur, -S- or -S-; m for a Is an integer from 1 to 5; η is 0, 1 or 2; ρ for or 3; q is 1, 2 or 3; and t is 0 or 1; with the caveat that a) .. if m stands for 2, one or both symbols R for -NH ₀ , -NR ⁸ H, -NR ⁸ , or: -C00R - stand un <ä- given- if a remaining symbol R ^{1 stands} for -CN, Cl, Br, J or -N0_; b) if m stands for 3, one of the symbols R for -NH ₃ , -NR ⁸ H, -jN « _a oäerNv. ^ x "R · stands and the remaining two I) ' Symbols R stand for chlorine, bromine or iodine; c) when m is 4 or 5, R is chlorine, bromine or iodine; d) η is 1 or 2 when m is 1 and R ^{1 is} -NH or 130009/0688 -NO "stands; and e) the sum of m and η is equal to or less than 5. 2. Silanes according to claim 1, characterized in that R for · -NH ₂ , -NrI? or -CHO. 3. Silanes according to claim 1, characterized in that R is for Propylene stands. 6 7 4. silanes according to claim 1, characterized in that R and R represent alkyl of 1 to 4 carbon atoms. 5. Silanes according to claim 4, characterized in that R and R stand for methyl. 6. Silanes according to claim 1, characterized in that η for O or 1 stands. 7. Silanes according to claim 1, characterized in that η stands for 1 and R ² stands for methyl. 8. Silanes according to claim 1, characterized in that R stands for CH-COO-, m stands for 2 and η stands for 0. 9. A method for the preparation of silanes according to claim 1, characterized characterized in that essentially practically equimolar amounts of an anhydrous alkali metal or alkaline earth metal compound of general formula or ^R q Haloalkylsilane of the general formula 130009/0688 in which M stands for an alkali metal or an alkaline earth metal and X stands for chlorine, bromine or iodine, reacts with one another, by adding the alkali metal or alkaline earth metal compound and the silane under practically anhydrous conditions Temperatures between room temperature and 200 C in a liquid reaction medium, which at least partially consists of at least a dipolar aprotic liquid and optionally a liquid boiling between 40 and 200 ° C Hydrocarbon exists, brings to reaction and in this case the reaction medium obtained is practically complete via a Conversion of the alkali metal or alkaline earth metal compound and the silane into the desired functional phenoxyalkyl, Thiophenoxyalkyl- or pyridyloxyalkylsilane keeps the reaction medium at a temperature of 40 to 200 ° C. for a sufficient period of time filtered to isolate the desired silane and the liquid reaction medium from the liquid phase evaporates. 10. The method according to claim 9, characterized in that X stands for chlorine. 11. The method according to claim 9, characterized in that M stands for sodium. 12. The method according to claim 9, characterized in that the dipolar aprotic solvent is dimethyl sulfoxide, N, N-dime thy 1 formamide, tetramethyl urea or hexamethylene phosphoramide is used. 13. The method according to claim 9, characterized in that the reaction between the alkali metal or alkaline earth metal 1 compound and the silane is carried out in an inert atmosphere. 14. The method according to claim 9, characterized in that the dipolar aprotic liquid makes up 1 to 100 wt. SS of the reaction medium. 130009/0688