CS223439B1 - N-/alkoxysilylmethyl/arylsulphonamides and method of preparation thereof - Google Patents

Description

The invention relates to N- (alkoxysilylmethyl) arylsulfonamides and a process for their preparation.

The technology for the preparation of silicone compounds based on alkyl, aryl or alkylarylsiloxanes has been carried out for several years. These compounds have significant properties in the field of plastics, paints and lubricants. To improve some of the properties of these compounds, many compounds are described in the literature that are a modification of these basic polysiloxanes. After a detailed study of the possibilities of influencing the properties of the organosilicon compounds, it has proved advantageous to investigate the hitherto unwritten modification by introducing an arylsulfamide group into the organosilicon molecule.

A process for the preparation of the N-alkoxysilylmethyl-aryl-sulfonamides of the formula I

CH-Si- (OR _{&) n} (I) wherein Ri, Rz, and R3 are each hydrogen, methyl or halogen, R₄, R₅ denote hydrogen or methyl · Re is methyl or ethyl, m = 0-3, n = 3 - m, according to the invention, consists in reacting the sodium or potassium salt of the arylsulfonamide of the formula II

(II) wherein Me is a sodium or potassium atom and R 1 to R 1 have the above meaning, with the halomethylalkoxysilane of formula III

X - CH 2 - Si - (OR e) n (R 5) _m (ΠΙ) where X is a chlorine or bromine atom and R 5, R 6, m and n are as defined above, in an N, N'-dimethylformamide medium at elevated temperature. The liberated potassium chloride or sodium chloride was separated from the reaction mixture by hot filtration. The N, N'-dimethylformamide is separated from the reaction mixture by vacuum distillation. The residue contains the technical product of N- (alkoxysilylmethyl) arylsulfonamide. These products are refined by vacuum distillation.

The examples below illustrate embodiments of the method of the invention.

Example 1

To a 0.5 L three-necked flask equipped with a thermometer stirrer and a condenser, terminated with a cap filled with calcium oxide, 90.0 g of benzenesulfonamide sodium, 106 g of chloromethyltriethoxysilane and 200 ml of dry N, N-dimethylformamide were added. The mixture was heated at 150 ° C for 6 hours. After this time, the mixture was cooled to about 100 ° C and the precipitated sodium chloride was aspirated. The cake was washed with hot Ν, Ν-dimethylformamide. The mother and wash filtrate was concentrated on a vacuum rotary evaporator to a temperature of 130 ° C at 40 mm Hg. The evaporation residue containing N (triethoxysilylmethyl) benzenesulfamide was distilled under vacuum, collecting a fraction of 180-192 ° C at 199.9 Pa in a yield of 94 g.

Elemental analyzes of the product:

H, 6.71; N, 4.21; S, 9.85. Example 2

Apparatus similar to Example 1. 91 g of chloromethyl (methyl iodoethoxysilane, 97 g of potassium benzenesulfamide and 250 ml of N, N'-dimethylformamide) were weighed into the flask and heated at 150 ° C for 4 hours. The precipitated potassium chloride was suctioned off, the cake was washed with hot N, N'-dimethylformamide, and the mother and wash filtrate was first decalted on a rotary vacuum evaporator to 170 ° C at 40 mbar. range 198-205 ^° C at 399.9 Pa in a yield of 97 g.

This fraction was distilled again and the boiling point of the final product N- (diethoxymethylsilylmethyl) benzenesulfamide was 190 ° C (186.6 Pa).

Example 3

Apparatus and procedure analogous to Example 1. 90 g of o-toluenesulfamide sodium salt, 107 g of chloromethyltrium thoxysilane and 200 g of N, N‘-dimethylformamide were charged into the flask. The reaction time was 4 hours at 120 to 125 ° C. After cooling, the precipitated sodium chloride was aspirated, the cake was washed with 3 x 15 g of N, N‘-dimethylformamide. The combined filtrates were first concentrated on a rotary evaporator to a temperature of 130 ° C and a pressure of 4.0 kPa and then vacuum distilled. A N-triethoxysilylmethyl-o-toluenesulfamide fraction having a boiling point of 215-225 ° C (399.9 Pa) was collected in a yield of 157 g. Example 4

Apparatus similar to Example 1. 107 g of sodium salt were weighed into the flask

4-chlorobenzenesulfamide, 106 g chloromethyltriethoxysilane and 200 ml dry N, N-dimethylformamide. The mixture was heated at 150 ° C for 6 hours. The reaction mixture was then cooled to about 100 ° C and the precipitated sodium chloride was aspirated. The cake was washed with hot Ν, Ν-dimethylformamide. The mother and wash filtrates were concentrated on a vacuum rotary evaporator to 130 ° C at 4.0 kPa. The residue contained N (triethoxysilylmethyl) -4-chlorosulfamide.

Analysis of the product found:

9.2% Cl, 7.2% Si.

pRedmE

Claims (2)

1. N- (alkoxysilylmethyl) arylsulfonamides of the formula I (OR ₆ ) '(where R 1, R 2, R 3 are each hydrogen, methyl or halogen, R 1, R 5 are hydrogen or methyl, R 6 is methyl or ethyl, m = 0 to 3, n = 3 - m. 2. A process for the preparation of N- (alkoxysilylmethyl jarylsulfonamides according to item 1 by reaction of an alkali metal salt of arylsulfonamides of formula II wherein Me is potassium or sodium and R1 to R1 are as defined above with a halomethylalkoxysilane of formula III X - CH 2 - Si - (ORej _n (R 5) _m (ΠΙ) scyl) - R 1r (Me) wherein X is a chlorine or bromine atom and R 5 and R 6, m and n are as defined above in N, N'-dimethylformamide 120-150 ° C, the crude product is isolated by vacuum rectification.