CH244579A - Process for the preparation of a water-soluble sulfonated condensation product. - Google Patents

Description

  

  Process for the preparation of a water-soluble sulfonated condensation product. It has been found that water-soluble condensation products with excellent capillary-active properties are obtained,

   if you respectively arylhydrazines. their sulfonic acids and aliphatic or alicyclic carboxylic acids with more than 5 carbon atoms or. their derivatives and compounds suitable for the acylation reaction with fewer than 8 carbon atoms that contain at least one atom grouping NHz-C @ respectively. Contain NH = C <,

   or substances that provide such compounds are condensed with one another and, if water-insoluble compounds are formed, these are sulfated. The process is best done in a more concentrated manner. fuming sulfuric acid carried out, with condensation and optionally sulfuration side by side he follow.



  The new water-soluble condensation products have a very good emulsification and Solvent power, especially for lime soap, also an excellent detergent power; but they can also be used as plasticizers. As arylhydrazines come into question: in the aromatic like unsubstituted or be arbitrary, z. B. by alkyl, alkogy, nitro groups, halogen, etc., compounds substituted, the free bases and the salts.

         In practical terms, it is important that the representation of the free hydrazine bases themselves is superfluous, since the salts, which are usually obtained as chlorohydrates in technology, give the best results. However, especially if their poor solubility favors isolation, the alkali metal salts of the aromatic hydrazine-N-sulfonic acids, but also sulfonic acids with nuclear sulfonic acid groups can be used.



  Of the aliphatic or alicyclic carboxylic acids with more than 5 carbon atoms, possible aliphatic compounds are: especially fatty acids, e.g.

   B. the pure compounds, but more advantageous the cheap commercial mixtures of higher fatty acids, such as those in the copra oil. Coconut oil or palm kernel fatty acids, in technical stearic acid u. a. m. exist;

    but also carbogyl-containing oxidation products from natural or synthetic paraffins are very suitable for the new process. As alicyclic carboxylic acids, which also include the carboxylic acids derived from aromatic compounds by hydrogenation, are:

       Naphthenic, resinous, campholic, fencholic, hexahydrobenzoic acid, dihydrobenzoic acid etc. Instead of the free acids, the derivatives which can be used for acylation reactions, such as the halides, anhydrides, esters, in particular glycerides etc., can also be used.

      As compounds with fewer than 8 carbon atoms, which contain at least one atomic grouping NHZ Cz, respectively. NH = C <, or substances that provide such compounds are possible:

   mainly amides of aliphatic carboxylic acids, such as acetamide, propionamide or ammonium acetate or propionate or urea and thiourea respectively. their derivatives, dicyandiamide, etc., but also simple aromatic acid amides, such as benzamide, etc., and also hexahydrobenzamide,

          Phenylacetic acid amide <B> ETC. </B> Theoretically, the reaction according to the invention can be thought of as broken down into several stages. It is very likely that the acylation of the aryl hydrazine to the aryl hydrazide occurs in the first stage, the formation of a 1-aryl-1,2,4-triazole and possibly finally the sulfonation takes place in the second stage. This view is justified in that practically the same end products are obtained if the condensation reaction is broken down into individual stages,

       For example, by using hydrazides from aromatic hydrazines and carboxylic acids according to the above definition with compounds with fewer than 8 carbon atoms which contain at least one atom group NHZ-C "'<B>' </B> or NH = C <, condensed and optionally subsequently sulfonated or by unsulfonated or low sulfonated 1-aryl-1,2,

  4-triazoles of the following general formula
EMI0002.0073
    where Ar is a substituted or unsubstituted aryl radical, R1 is an aliphatic or alicyclic radical with more than 4 carbon atoms and R2 is hydrogen NH. or an organic radical with a maximum of 7 carbon atoms, sulfonated.

   The aryl hydrazides which can be used as starting compounds are known; the preparation of the spe cial 1-aryl-1,2,4-triazole compounds he follows according to the usual procedure for the preparation of 1,2,4-triazole.



  The subject of the present patent is a process for the preparation of a water-soluble sulfonated condensation product. The process is characterized in that one uses phenylhydrazine, a compound which releases the stearic acid residue, such as B. stearic acid, its halides, esters or its anhydride, acetamide and a sulfonating agent can act on each other.

   The alkali salts of the new, sulfonated triazole compound are light-colored powders that are easily soluble in water. They are intended to be used as textile auxiliaries. Example <I> 1 </I> 14.5 parts of phenylhydrazine chlorohydrate or 18.8 parts of phenylhydrazine-N-sulfonic acid are dissolved in 60 parts of sulfuric acid monohydrate and 28 parts of technical stearic acid are added. It is stirred until everything is resolved.

   Then 6.0 parts of acetamide are gradually introduced at 20-30 and stirred for one hour. At 20-30, 40 parts of fumes of sulfuric acid (26% SO3) and at 0-10 the same amount of 66% oleum are added dropwise. After stirring for 15 hours, the reaction mixture is poured onto an ice-common salt mixture and the sulfonic acid which has separated out is separated off. After neutralization with sodium hydroxide solution and evaporation, the sodium salt of sulfonic acid is obtained.

   It has excellent washing power and very good emulsifying and dissolving power for lime soap. <I> Example 2: </I> 10.8 parts of phenylhydrazine and 28.4 parts of technical stearic acid are heated to 80 in vacuo and 3'7.5 parts of the phenylhydrazide stearic acid formed are dissolved in 60 parts of sulfuric acid monohydrate with stirring. Then 6 parts of acetamide are gradually entered at 20-30 and the mixture is slowly heated to 50.

   Then 30 parts of 26% oleum at 20-30 and 30 parts of 66% oleum at 0-10 are added dropwise and the whole is stirred for 15 hours at 20-25. The sulphonation mixture is then poured onto an ice-common salt mixture, the separated sulphonic acid is separated off, neutralized with sodium hydroxide solution and evaporated.

   The sodium salt of sulfonic acid is thus obtained in the form of a light powder. <I> Example 3: </I> 30 parts of the stearic acid phenylhydrazide obtained according to Example 2 from phenylhydrazine and stearic acid and 9 parts of acetamide are dissolved in 100 parts of dry benzene and 14 parts of anhydrous zinc chloride are added.

   The reaction is then refluxed well with stirring for 15 hours. After the benzene has evaporated, the contents of the flask are poured into water and extracted with ether. 20 parts of the 1-phenyl-3- "heptadecyl" - 5-methyl-1,2,4-triazole obtained after the removal of the ether during distillation of the residue are dissolved in 30 parts of sulfuric acid monohydrate with stirring.

   Then gradually add 20 parts of 26% oleum at 10-20 parts and 20 parts of 66% oleum at 0-10 and stir for 15 hours at 20-25. The sulfonation mixture is then poured onto ice and worked up as indicated in Example 2.

 

Claims (1)

PATENT CLAIM: Process for the production of a water-soluble, sulfonated condensation product, characterized in that phenylhydrazine, a compound giving off the stearic acid residue, acetamide and a sulfonating agent are allowed to act on one another. The alkali salts of the new, sulfonated triazole compound are light-colored powders that are easily soluble in water. They are to be used as textile auxiliaries. SUBClaims 1. The method according to claim, characterized in that phenylhydrazine, a compound which releases the stearic acid residue, and acetamide are condensed in sulfuric acid and the condensation product is treated with a sulfonating agent without isolating it. 2. Process according to patent claim and dependent claim 1, characterized in that phenylhydrazine is used which was formed from one of its salts during the reaction. 3. The method according to claim and dependent claim 1, characterized in that phenylhydrazine is used which was formed from its N-sulfonic acid during the reaction. 4th Process according to claim, characterized in that phenylhydrazine is acylated with a compound which releases the stearic acid residue, the resulting isolated stearic acid phenylhydrazide is condensed with acetamide in sulfuric acid and the condensation product is treated with a sulfonating agent without isolating it. 5. The method according to claim, characterized in that phenylhydrazine is acylated with a compound releasing the stearic acid residue, and condensed with acetamide to give 1-phenyl-3- "heptadecyl" -5-methyl-1,2,4-triazole the isolated condensation product is treated with a sulfonating agent.