CS210028B1 - Tenzides on the base of the ethylenediaminotetravinegar acid derivatives and method of making the same - Google Patents

Description

SOCIALISTIC AND DESCRIPTION OF THE INVENTION <19> TO COPYRIGHT CERTIFICATE 210028 (11) (Bl)

/ 22 / Registered 29 12 79/21 / / PV 9576-79 / (51) Int. Cl.3C 11 D 1/10

OFFICE OFFICE

& DISCOVERY (40) Published 31 10 80 (45) Published 15 07 8 2 (75)

BUTVIN PETER, Ing. MAJER JAROSLAV prof. Prof. RNDr. DrSc. , BRATISLAVA

and NOVÁK JAN ing. , RAKOVNÍK (54) Ethylenediaminetetraacetic acid derivative surfactants and preparations 1 2

The present invention relates to surfactants from the group of ethylenediaminetetraacetic acid derivatives of EDTA characterized by the general formula

XOOC-CH 2 R CHO-COOX 1/3 n-ch 2 -CH 2 X 10 C-CH 2 X x CH 2 -COOX where the alkane chain is from 5 to 18 carbon atoms and X is H or Na or K or NH 3 and the process for their preparation. EDTA derivatives of the aforementioned structure are currently known &amp; carbon chain to R = C 4 H 9, prepared by condensation of halo-acetic acid with the corresponding diaminoalkanes in an alkaline medium (Droyer R. et al., J. Am. Soc., 81, 2955, (1959); Novák V.a kol .; Chem. rumors 23, 161/1969 //. Once-prepared surfactants based on another structure result in hydrogen substitution at one or two carboxy-methyl groups EDTA (Takeshita, T. et al., Yukagaku, 19, 984 (1970)); Miyake T. et al., Yukagaku, 21, 416 Jill /.

SUMMARY OF THE INVENTION The present invention relates to surfactants derived from ethylenediaminetetraacetic acid characterized by the general formula XOOC-CH2R, CH2-COX1S-CH-CH2-N, OOCOCCH2CH2-COOX wherein R is CnH2 + ian is 5 to 18 and X is H or K or Na or NH 4. The process for their preparation consists of adding 0.5 to 1.5 parts by weight of the corresponding 1, 2-diaminoalkane and 5 to 18 carbon atoms in the chain in the presence of hydroxyliones and 5 to 18 carbon atoms in the presence of hydroxylionic acid and after reacting the condensation product is acidified.

The subject matter of the invention is described in the following examples without limiting the examples. EXAMPLE 1 4.73 g (0.05 mol) of monochloroacetic acid was neutralized with 10 ml of 5N sodium hydroxide solution. Subsequently, 1.45 g (0.01 mol) of 1,2 diaminooctane was added to the neutralized acid with stirring, followed by an additional 8 ml of 5N sodium hydroxide. By thorough mixing, the mixture is non-kalastate at room temperature for three days.

Thereafter, the reaction mixture was acidified with 5N hydrochloric acid to a pH of 1.5-2. From the solution, the amorphous substance was dissolved, preferably in 50% ethanol, and crystallized. The material was filtered under vacuum, washed with 50% aqueous ethanol, dried to dryness and weighed. The yield was 50.2% calculated on the 1,2-diaminooctane used. The 1,2-diaminooctane-N, N, N, N-tetraacetic acid obtained, m.p. 189.5-191 ° C, is purified by recrystallization from water, 50% ethanol or other water-miscible solvent.

For example, 210028 210028 1,2-diaminodecanic acid, respectively, is prepared in the same manner. 1,2-diaminododecane-NN, N ', N -, tetraacetic acid with 39 X and 50 Z, respectively, Example 2 9.5 g (0.1 mole) of monochloroacetic acid were neutralized under laboratory conditions with 20 ml of 5N sodium hydroxide. 5.15 g (0.02 mol) of 1,2-diaminohexadecane in 60 ml of 95% ethanol was added to the tomo solution. The mixture was refluxed for 20 hours during which time a portion of 16 ml of 5N sodium hydroxide was added to make 10-11. A further 1.9 g (0.02 mol) of monochloroacetic acid was then added to the reaction mixture, neutralized with 4 ml of 5N sodium hydroxide, and the reaction was continued for 10 hours under the above conditions. After completion of the reaction, the mixture was poured into 300 mL of dist. water and acidified to pH 1.5-2 with 5N hydrochloric acid. The precipitate formed was filtered off, washed with distilled water into the negative chloride ions in the filtrate, dried to a pH of 2 and weighed. The yield was 7.3 gt. 74.7 calculated on 1,2-aminohexadecane used. The 1,2-aminohexadecane-Ν, Ν, Ν-, N *-tetraacetic acid obtained, m.p. 171 DEG-173.5 DEG C., is purified by recrystallization from 70 to 98% acetic acid. Example 3 Surfactants prepared from the group of ethylenediaminetetraacetic acid derivatives, 1,2-diaminooctanetetraacetic acid

Table 1

The wash performance test of Example 1, 1,2-diamino-decanetetraacetic acid, 1,2-diaminododecanetetraacetic acid and 1,2-diamino-hexadecanetetraacetic acid according to Example 2 was evaluated by the smoothness of the wash solution in the form of solutions of their four-salt salts. polyester-cotton fabric at 45 ° C, respectively. 90 [deg.] C. and compared to the actual ability of the mixture of active substance and tri-polyphosphate for each case in a concentration of 1 g / l and 3 g / l wash solution. The results are shown in Table 1. The prepared derivatives were subjected to surface tension at 25 ° C, at a concentration of 1 g / l, 0.5 g / l and 0.125 g / l solution by conventional method. The results are shown in Table 2. The advantages of the surfactants of the ethylenediaminetetraacetic acid derivative family and their preparation are broadly applicable and in simple preparation and isolation at 35% yields. The prepared compounds retain the chelating effect of the functional ligand, some of which exerted the effect of ethylenediaminetetraacetic acid. In the analytical chemistry, it is useful for separation by cation separation methods or in the determination of non-aqueous or mixed solvents. However, the main advantages of the use of these substances are in the presence of the presence of surfactants or chelating agents, the skulls act as detergents or additives, emulsifiers, wetting agents, flocculants, flocculants. -Active Reagents and the like. The new surfactants of this type enhance the range of previously known betaine amphoteric drugs.

Fabric mixed fabric - PES / BApri 45 ° C cotton at

fabric90 ° C 1 g / 1 3 g / 1 X 1 g / 1 3 g / 1 X DOTA 8.4 * 1, 4 36.4 * 2.3 40.5 * 1.5 15.8 * 2.4 39.7 * 1, 5 33.7 * 1.5 DDTA 6.9 * 1, 6 35.0 * 2.4 37.3 * 4.5 2.3 * 0.5 39.9 * 0.9 40.0 * 3.1 DDDTA 3.5 * 0.5 42.5 * 1.1 17.2 * 5.0 2.0 * 0.4 46.3 * 1.3 34.8 * 1.3 DHDTA 5.5 * 1.4 52.4 * 1.5 17.4 * 5.9 5.2 * 1, 1 61.3 * 2.3 39.2 * 2.6

Legend: DOTA - 1,2-diaminooctanetetraacetic acid DDTA - 1,2-diamino-dodecanetetraacetic acid DDDTA - 1,2-diaminoododecanetetraacetic acid DHDTA - 1,2-diaminohexadecanetetraacetic acid tested as their sodium salt solutions X - 0,6 g active of tripolyphosphate per liter

Table 2

Surface tension / at 25 ° C in mil N / m / Substance

Concentration 1 g / 1 0.5 g / 1 0.25 g / 1 0.125 DOTA 49.0 - - - DDTA 56.5 - - - DDDTA 41, 0 47.0 52.0 - DHDTA 42.0 42.5 46,5 Legend: DOTA - I, 2-diaminooctanetetraacetic acid DDTA - I, 2-diaminodecanetetraacetic acid DDDTA - 1, 2-diaminododecanetetraacetic acid DHDTA - 1, 2-diaminohexanedecanetetraacetic acid tested as solutions of their four-salt salts

Claims (2)

210028 OF THE INVENTION CLAIMS 1. Surfactants from the group of the ethylenediaminetetraacetic acid derivatives, in general the formula XOOC-CH2-CH2N-CH-CH2 XOOC-CH2 CH2-COOX CH2-COOX-n; wherein R is + p n is 5 to 18 and X is H or Na or K or 2. A process for the preparation of surfactants according to claim 1, wherein from 0.5 to 1.0 parts by weight of 1,2-diaminoalkane having 5 to 18 carbon atoms in the chain in the presence of free hydroxyl ions are added to the 5 parts by weight of neutralized monohaloacetic acid and the product precipitates upon reaction. by acidification with mineral acid. Søverografia. node 7 »Moet