SU405352A1 - Method of obtaining aromatic silicon-containing isocyanates - Google Patents

Description

14 The invention relates to the field of producing aromatic silicon-containing isocyanates where R is the same or different H, halogen, alkyl, aryl, alkoxy or aryloxy, and also from substituted derivatives. Compounds of this kind, in particular with hydrolysable groups on silicon, can be used to produce silicon-modified polymeric materials, such as polyurethanes, polyureas, and others, as well as a feedstock in the synthesis of other hard-to-reach materials.

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-y2Ks $ 1C1 where R is the same or different H, gapogen, alkyl, aryl, alkoxy or aryloxy, or their substituted derivatives; R - H, alkyl, aryl, halogen; M - magnesium or alkali metal. O -, M - and n-haloanilines silylated with nitrogen can be used as starting products. Compound III was synthesized either under the conditions of the Grignard reaction, or using alkali metals (Li, Na, K) by adding compound II to the mixture of halogenosilane and alkali metal in an inert organic solvent. As such solvents, benzene, toluene, xylene, sulfuric ether, tetrahydrofuran can be used; other. The reaction of compound III with phosgene is carried out at a temperature. 0-150 ° C (preferably at 20-50 ° C, both in and without inert organic solvents. The order of addition of the reagents does not affect the yield of the target products 1, which in all cases is close to quantitative, Iii.

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fTf yassov organosilicon compounds. In the literature, the synthesized products are not described. The only known compound of this type is p-trimethylsilylphenyl isocyanate, obtained by heating a difficult-to-reach azide Jt r-trimethylsilylcarboxylic acid. To simplify the process and to obtain a number of new compounds, a method of producing such compounds has been proposed. It consists in the interaction of N, N-bis-silyl halogenanilines with magnesium or alkali metals in the presence of organohalogenesilanes in the RjSicE solvent medium, followed by treatment of the resulting organosilicon anilines with phosgene. Isocyanates I, which contain Si-H or Si-OR groups by the action of halogenating agents, can easily be converted into even more valuable manomeric products — halogen lylphenyl isocyanates suitable for the preparation of NCO-terminated oligosiloxanes. The proposed method for producing silicon-containing aromatic isocyanates is simple in hardware design and easy to implement on an industrial scale. Example 1. Trimethylsilylphenyl isocyanate. A. To a mixture of 3.1 g (0.128 g-atom) activated by iodine MR and 32.6 g (0.192 mol) of (CH3) jSiCt in 150 ml of absolute tetrahydrofuran are added at boiling 1-2 ml of N, N-bic- ( dimethylsilyl) -n-bromoaniline and after the start of the reaction, the rest of the product is added (altogether .37 g or 0.128 mol) K, K-bis- (dimethylsilyl) -l-bromoaniline. Upon completion of the addition, the mixture is boiled under stirring for 6 hours, the MgCfBr precipitate is filtered off, washed with absolute ether and the filtrate is distilled. 29.3 g of N, N-bis- (dimethylsnlil) -n-three are obtained.

Claims (1)

1 WAY OF OBTAINING AROMATIC.! SILICON-CONTAINING ISOCYANATES / characterized in that, in order to simplify the method and increase the number of final products, Ν, Ν-bissilyl-substituted halogenanilines are reacted with magnesium or alkali metals in the presence of organohalogenosilanes in a solvent medium, followed by treatment of organosilicon anilines obtained with this.