CS247566B1 - Benzdjamidoetylalkylimidazolíny - Google Patents

Abstract

In the formula Rp represents R2 alkyl or alkenyl radical. with 7 to 22 carbon atoms, R2 phenylene and their ammonium salts. The compounds are suitable as lubricants for the surface treatment of glass fibers. They can be prepared by condensation of fatty acids with diethylenetriamine to the corresponding imidazoline, which is further reacted with the corresponding benzenedicarboxylic acid or anhydride.

Description

The invention relates to benzdiamidoethylalalkylimidazolines and light ammonium salts.

Alkylimidazolines have found widespread application as textile lubricants, antistatic agents, emulsifiers, corrosion inhibitors and epoxy resin hardeners.

The synthesis of these compounds is usually accomplished by condensation of fatty acids with aliphatic polyamines. A number of these derivatives are known whose preparation with modification is carried out in view of their application / US Pat. No. 2 200 815, 2 267 965,

268 273, 2,355,837, 2,966,478, 3,002,941, 3,474,056, USSR Pat. No. 214,718, British Pat. No. 865 656 and EP No. 0 075 170].

Fatty acid-based alkylimidazolines have also found application as glass fiber coating lubricants. The treated coil fibers are dried in the manufacturing process, usually using continuous driers. The evaporation of the water contained in the coils leads to convection, i.e. migration, flow or flow of liquid and gaseous media, to the formation of an uneven lubricant deposit, which then negatively affects further textile processing of the fibers. In the research of the compounds of the invention, they have been found to have minimal migration and are suitable as glass fiber lubricants used as plastic reinforcement.

The invention relates to benzdiamidoethylalkylimidazolines of the general formula.

CH ₂ - CH ₂ OK, - CH »

II N ² I ² n / CH _2/2 -NHCO-R »CONH / CH _2/2 n in N /

Where I represents

R @ 1, R @ _{2 is an} alkyl or alkenyl radical having 7 to 22 carbon atoms; R @ 1 is phenylene and their ammonium salts.

The preparation of these compounds can be carried out as follows. Condensation of fatty acids with diethylenethylamine in a 1: 1 molar ratio gives the corresponding alkylimidazolines. Fatty acids are used either individually, but most often in mixtures as fatty acids isolated in various oils and fats.

The prepared alkylimidazolines are reacted with phthalic anhydride or phthalic acid, isophthalic acid, terephthalic acid or their ester, optionally with technical mixtures based on them in a molar ratio of 2: 1. By neutralization with organic or inorganic acids such as formic, acetic, propionic, hydrochloric, phosphoric and the like, they can be converted, if necessary, to the corresponding ammonium salts, also called imidazolinic salts. In this way it is possible to regulate a number of properties such as hydrophilicity, consistency, melting point and the like.

The invention is further elucidated by way of examples in which the composition is given in weight concentration.

Example 1

To a sulfonation flask equipped with a stirrer, contact thermometer, nitrogen inlet and azeotropic was charged 500 g of a technical mixture of fatty acids of the composition shown in Table 1.

Table 1 acid (%) wt.

stear 52,4 palmitic 42,3 laur 1,9 arachic 0,7 caprylic 0, i pentadecane 0,3 heptadecane 1,7 capric 0,3 unidentified 0,3

100 g of xylene and 180 g of technical diethylenetriamine having an amine number of 1,638 mg KOH / g were added to the fatty acid melt. The batch was heated to boiling point and condensation and cyclization to imidazoline was allowed to proceed until completion of the reaction water evolution.

Xylene and volatiles were distilled off under vacuum. From the alkylimidazoline thus prepared, 70 g, 16.8 g of the appropriate benzenedicarboxylic acid listed in Table 2 and 10 ml of xylene were introduced into the azeotropic apparatus. The batch was heated to boiling point and the reaction was terminated after separation of the reaction water followed by distillation of xylene. The properties of the prepared imidazolines are shown in Table 2.

Table 2 Acid Melting point Nitrogen content determined (%) calculated / ° C /

phthal 57 to 59 10.7 11.2 isophthalic 5 58 to 60 11.6 11.2 tereftalová 61 to 63 10.9 11.2

Example 2

198 g of the technical grade listed in Table 3, 72 g of diethylenethylamine and 30 of a mixture of liquid fatty acids of ml xylene were introduced into the apparatus.

Table 3 acid / t / wt.

oil 83.4 linoleic 10.4 linolene 3.6 stearic 1.2 nonidentified 1.4

The batch was maintained at the boiling point until the cyclization to the alkylimidazoline was complete while separating the reaction water. After this time, 52 g of phthalic anhydride was added and the reaction was complete after the reaction water was released. Xylene and volatiles were distilled off under vacuum. Prepared imidazoline at 20 ° C of a honey-like consistency, m.p. 18-20 ° C with a nitrogen content of 10.6% by weight. (calculated 10.1 wt.%).

Example 3

As in Example 2, imldazoline was prepared by reacting a batch of 150 g of a technical mixture of fatty acids of the composition shown in Table 4, 73 g of diethylenetriamine and 53 g of phthalic anhydride.

Table 4 acid (%) wt.

lauric 50.8 myrist 13.8 palmitic 11.6 capric 8.1 caprylic 7.8 oil 3.7 stitch 1.2 unidentified 3.0

The prepared imldazoline has a honey-yellow consistency at 20 ° C with a melting point of 29-31 ° C, with a nitrogen content of 12.2% by weight. (calculated 11.9 wt.%) Water-dilutable hydrophilic salts can be prepared by neutralization with strong acids. The prepared imldazoline having an average molecular weight of 680 in an amount of 5 g was melted and neutralized with acid under stirring and dissolved in 500 ml of water to form opalescent solutions. The acid and its amount are shown in Table 5.

Table 5 Formic acid, hydrochloric acid

Example 4 weighing / g /

0.7

1.4

The fatty acid-phthalic acid imldazoline of 830 average molecular weight prepared according to Example 1 was used for the surface treatment of eclened fibers in the form of a 1% solution in water which was neutralized with 2 moles of acetic acid per mole of imidazoline. The fatty acid-based imldazoline as in Example 1 and tetraethylenepentamine were evaluated in the same manner in a molar ratio of 2 < 1. The treated glass fibers in the form of coils were tapered at 125 ° C for 4 h. Migration was evaluated by determining a migration coefficient which indicates the ratio of the lubricant weight on the outside of the coils to the weight of the lubricant on the inside of the coil.

Using the imidazoline according to the invention, the migration coefficient of 1.3 was reached, and in the case of imidazoline based on tetraethylenepentamine 1.8. In this way, the glass fibers have the same textile properties in the entire bobbin volume.

Claims (1)

OBJECT OF THE INVENTION Benzdiamldoetylalkylimldazolíny formula CH ₂ -CH ₂ CH, —CH, (N- (CH ₂ ) -NHCO-R 3 -nhco- (CH ₂ ) _-2 -n) NC ₂ where R is R, R1 is an alkyl or alkenyl radical of 7 to 22 carbon atoms, phenylene and light ammonium salts.