CS210308B1 - Organosilicon imido acids and their preparation - Google Patents

Abstract

The invention describes new silanes suitable for the treatment of glass fibers, of the structural formula /HOOCCH = CHC0/2 N /CH2/3 Sí /OR/ where R is methyl or ethyl. By neutralizing these silanes, they can be converted into the corresponding salts, for example: ammonium, alkyl ammonium and based on aliphatic polyamines. The transport of these compounds can be carried out by the action of 3-aminopropyltrimethoxysilane or -triethoxysilane on maleic anhydride. The reaction is conveniently carried out at a temperature of 10 to 110 ° C in an environment of water-soluble diluents, optionally in the presence of a polymerization inhibitor.

Description

The invention relates to new organosilicon imido acids, their salts and the method of their preparation.

Organosilicon compounds, especially variously substituted trialkoxysilanes, have found wide application in the modification and silylation of various surfaces, mainly silicate ones, in order to achieve their special application properties, such as the preparation of heterogeneous catalysts, the treatment of fillers for plastic reinforcement, the hydrophobicization of various materials, the modification of chromatographic carriers, the treatment of textiles and paper, the anti-corrosion treatment of metals, etc.

The constantly expanding application use and new technologies for processing glass fibers have also been reflected in the new requirements placed on organoceramic compounds when applied to lubricating compositions. As a result, a whole range of different substituted trialkoxysilanes with special application properties is known, mainly the variously substituted trimethoxysilanes and triethoxysilanes, which are of particular importance /Noll WJ Chemie und Technologie der Silicone, Verlag Chemie Í968 and Ranney MW; Silicones, Vol. I, II, Noyes Data Corp. ₅ New Jersey» 1977/.

Substituted trialkoxysilanes with carboxyl groups are known (U.S. Pat. Nos. 3,627,806 and 3,922,436). A variety of different N-substituted aminosilanes are also known (U.S. Pat. Nos. 3,627,806 and 3,922,436).

934,459, 3,317,577, 3,458,556 and 3,956,353, Brit. pat. no. 1,409,483 and 1,458,533/.

Japanese Patent No. 76 108 022 describes the preparation of amidosilanes of the formula

R.C0NH/CH_/ Si/OR/

2 n 3 where R is alkyl, R ₁ is alkyl, alkenyl, aryl by the action of acyl chlorides on the corresponding arainosilanes.

The invention describes novel organosilicon imido acids of the general formula /hoocch=chco/ ₂ n/ch ₂ / ₃ s/or/ ₃ where R is methyl or ethyl and their salts.

The preparation of these compounds can be carried out by the action of maleic anhydride on aminosilanes of the general formula nh ₂ /ch ₂ / ₃ s/or/ ₃

i.e. using 3-aminopropylmethoxysilane and 3-aminopropylmethoxysilane in the medium of organic diluents, such as chloroform, diethyl ether, preferably water-soluble . . . diluents, such as acetone, dioxane, etc. at a temperature of 10 to 110 C. ₃ optionally in the presence of a polymerization inhibitor. Silanes can be converted into the corresponding salts by neutralization with inorganic or organic bases. In the case of glass fiber treatment, ammonium, alkyl ammonium and aliphatic polyamine-based salts are of greatest importance.

The silanes according to the invention are useful as so-called antimigration agents in lubricating compositions for the treatment of glass fibers. Since they are dicarboxylic compounds, they can also be used in the preparation of various polymers as a raw material.

The invention is further illustrated by way of examples.

Example 1

The preparation of the silane of the formula /HOOCCH=CHCO/-N/CH ₂ / ₃ Si/OC ₂ H ₅ / ₃ was carried out in a flask equipped with a stirrer, a reflux condenser with a drying tube, a separating funnel and a contact thermometer.

Handle:

39.2 g /0.4 mol/ of raalienanhydride

44.3 g /0.2 mol/ 3-aminopropylethoxysilane g acetone

Acetone and maleic anhydride were added to the flask. After its dissolution due to the endothermic process of dissolution, the temperature stabilized at 12 to 15 °C. Then, silane was slowly added so that the temperature did not exceed 40 °C and the batch was maintained at a gentle reflux for 1.5 h. After distilling off the acetone, 80 g of silane was obtained.

0 = 1.4865

Analysis for C^U^O^NSi /mol. weight - 417.55/

with lily You are acidity number /mg KOH/g/ calculated 3.35 b,Ti 268.75 established 3.23 6.81 275.20

Example 2

The preparation of the silane of the formula /hoocch=chco/ ₂ n/ch ₂ / ₃ s/och ₃ / ₃ was carried out in the apparatus described in Example 1.

Handle:

39.2 g /0.4 mol/ maleic anhydride

35.8 g /0.2 mol/ 3-aminopropyltrimethoxysilane g acetone

Preparation procedure as in Example 1.

Analysis for ^C ^4 ^H 21°9 ^NS ^ mass - 375.41 /

N /%/ Yes /2/ acidity number /mg KOH/g/ calculated 3.73 7.48 298.92 established 3.61 7.60 305.16

Example 3

Silanes are soluble in most organic polar solvents. They are practically insoluble in water under normal conditions. Since water is used as a carrier medium in the preparation of lubricating compositions, it is advantageous to solubilize the silanes by neutralization using water-soluble bases. In this way, it is possible to prepare clear, stable aqueous solutions which can be further mixed with conventional lubricating agents used for the treatment of glass fibers. The amine was dissolved in 200 ml of water and 5 g of the silane from Example 1 was added with stirring.

1. The type and amount of amine is given in the table.

amen l&í

Ammonia 25% 1.6 monoethanolamine 1.5 triethanolamine 3.6 diethylenetriamine 1.5

Claims (2)

210308 amine / 8 / ammonia 25% 1,6-monoethanolamine 1,5-triethanolamine 3,6-diethylenetriamine 1,5 SUBJECT OF THE INVENTION What is claimed is: 1. Magnesium silicon imidoacids having the general formula (Hoocch = Chco / 2n / ch2 / 3si / or) WeRjemetylaleboetylaichsoli. 2. A process for the preparation of compounds according to claim 1, characterized in that the sdoma of the aminosilanes of the formula NH2 / CH2 / 3Si / OR / 3 wherein R has the same meaning as in 1, in an organic diluent soluble at 10 to 110 ° C, optionally in the presence of an inhibitor-treated compound, optionally by neutralization to the corresponding salts. preferably maleic anhydride, preferably in water-polymerization, and in porography. n. p., race 7. Most