CS265638B1 - Process for producing aminoamides - Google Patents

Abstract

The method for producing aminoamides according to the invention consists in the hydrolysis of a melt of a lactam of the general formula, where n = 3 to 12, in the presence of an organic and/or inorganic acid and/or their acid salts, whose dissociation constant K is greater than 1.10“5, in an amount of 0.01 to 10% by weight and for a period of 5 to 30 min. The mixture is then heated to 100 to 150 °C, diaminodiphenylmethane is added in a molar ratio of 1:1 to 1:4 based on the starting lactam and allowed to react for 5 to 30 min. The reaction can also take place in the presence of a low molecular weight anilinoformaldehyde resin. The aminoamides produced in this way are used as hardeners for epoxy resins and as modifiers for aminoplasts.

Description

The invention relates to a process for the production of amino amides for use in the manufacture of thermosetting plastics.

Aminoafcides are promising components for the preparation of polymers with specific requirements for their utility and rheological properties. They are used in particular as hardeners of epoxy resins and molding compounds and aminoplast modifiers. The prior art processes for their preparation are quite complex, for example according to DE-OS 2 627 070 they are based on the reaction of unsaturated fatty acids, the polyalkylene polyamide of isophorenediamine. In addition, the starting materials are difficult to access and expensive.

These disadvantages are overcome by the process for the preparation of aminoamides of the general formula

O

where x., x_, X-, is -H, or -C- (CH-) -NH_i z j μ z n z

0 and n = 3-12. The essence of the process is that the lactam melt of the general formula

O = C - N- H where n = 3 to 12 < ^Cl 2> n is hydrolyzed in the presence of an organic and / or inorganic acid with a dissociation constant of -5

K greater than 1.10 or in the presence of their acid salts in an amount of 0.01 to 10% by weight, and for 5 to 30 minutes. The mixture is then heated to 100-150 ° C, diaminodiphenylmethane is added in a molar ratio of 1: 1 to 1: 4 based on the starting materials, and the mixture is allowed to react for 5 to 30 minutes. In another aspect, the reaction is carried out in the presence of a low molecular weight anilinform aldehyde resin having a melting point of 35 to 111 ° C in an amount of 0 to 35% by weight based on the diaminodiphenylmethane content.

The following examples illustrate the process for the preparation of the aminoamides of the present invention.

He did

To molten 100 g of pure 6-caprolactam at 80 ° C is added 1.1 g of 80% formic acid, after 20 minutes the melt is heated to 132 ° C over five minutes, 151.15 g of diaminodiphenylmethane is added and after 20 minutes The melt is poured onto an aluminum foil and ground to a powder after solidification. The amine amide has a melting interval of 38-66 ° C, a melting point of 53 ° C, and a melting enthalpy of 79.168 µg as determined by DSC.

Example 2

To the molten 100 g of 90-C 8-caprylolactam is added 5 g of ammonium salt of p-toluenesulfonic acid. After 15 minutes, 47.5 g of technical diaminodiphenylmethane, trade name MDAP, containing 20% anilinoformaldehyde resin is added. The mixture was heated to 120 ° C during a rain minute and allowed to react for 30 minutes. The liquid aminoamide is characterized by a freezing point of +7.2 ° C. The aminoamide thus prepared can be isolated from an alcoholic solution by crystallization or precipitation with water.

1.

Example 3

To molten 100 g of 12-laurolactam at 100 ° C was added 7 g of acetic acid, after 25 minutes the melt was heated to 132 ° C over five minutes, 170 g of diaminodiphenylmethane was added, and after 20 minutes the melt was cooled. The resulting aminoamide had a melting interval of 15-29 ° C, a melting point of 21 ° C, and a melting enthalpy of 63.517 µg as determined by DSC.

Claims (2)

1. A process for producing amino amide of formula CH _2, C- (CH _{2) n} -NH ₂ where x, x. ,, X, it is -H or -C (CH _O) -NH _O 1 2 '3 ^J 2 n 2 and n = 3 to 12, characterized in that the lactam melt of the general formula O = C - N - H, where n = 3-12 ((CH _O) ^ 2 n is hydrolyzed in the presence of 0.01 to 10 wt. organic and / or inorganic acids and / or their acid salts with a dissociation constant K of greater than 1.10 ⁵ for 5 to 30 minutes, after which the mixture is heated to 100 to 150 ° C, diaminodiphenylmethane is added in a molar ratio of 1: 1 to 1: 4 based on the starting lactam and allowed to react for 5 to 30 minutes. 2. A process according to claim 1, wherein the reaction is carried out in the presence of a low molecular weight anilinformaldehyde resin having a melting point of 35 to 111 [deg.] C. in an amount of 0 to 35% by weight. based on the diaminodiphenylmethane content.