DE761081A - - Google Patents

Description

I.G. FARBENINDUSTRIE AKTIENGESELLSCHAFT

Patent department

LEVERKUSEN-I. G. WERK, November 18th

J 45 926 lYo / 12 ο
74

Process for the preparation of water-soluble or distributable eja · "condensation products.

It has been found that they are soluble in water or distributable Eondensationsprodukt ^ can get if one reactive organic VerbinaunJefbJP ^ m which the reactive Groups from one or more oxy and / or amino and / or carboxyl and / or carboxamide and / or sulfonic acid amide groups exist, with at least η + 1 mol of glycide implemented, where η is the number of reactive Means hydrogen atoms.

The conversion of these compounds with glycid creates substances that are now due to the content of lyophilic groups are much more easily soluble or dispersible in water than the starting materials.

Possible starting materials are: A

or polyvalent oxy compounds and their substitution products, e.g. η-butyl, primary n-dodecyl, primary n-octadecyl alcohol, Oleic alcohol, castor oil, glycerol, sorbitol, starch, phenol, cresols, xylenols, naphthols, dioxyphenols, salicylic acid esters; monovalent and polyvalent aliphatic and aromatic primary or secondary amines or secondary ring nitrogen bases, e.g. Butylamine, primary n-octadecylamine, benzylamine, hexahydroaniline, Dibutylamine, piperidine, morpholine, diethylolamine, ethylenediamine, Aniline and its homologues and substitution products, naphthylamines, arylenediamines, naphthylenediamine, ethylaniline »Diphenylaminej Aminophenols, amino alcohols; mono- and polyvalent carboxylic acids, such as butyric acid, lauric acid, palmitic acid, oleic acid, linoleic acid, coconut fatty acid, ricinoleic acid, lactic acid, maleic acid,

_ 2 -

Tartaric acid, adipic acid, oleylglycine, stearylsarcosine, benzoic acid, phenylacetic acid, anthranilic acid; Amides of carboxylic acids and organic sulfonic acids, provided there are still substitutable hydrogen atoms on their nitrogen atom and / or if any nitrogen substituents present contain hydroxyl groups, such as ζ. ! jjTnyutyramid, Milchsäur e-IT / B oxyä thy / - amide, oleic acid amide, palmitic acid-N- / S-oxyäth; £ l7-ajnid, Linolensäureanilid, ricinoleic acid-IT / S _t y ^{dioxypropyl7:} ami'l , H-Buty! -Benzamide, salicylic acid-I ^ naph-thyl- (1) - or - (2} J-3Mla, phthalimide, phthalamic acid, o- or p-toluenesulfonic acid-H-cyclohexyl-amide, U, N ' -Dilauryl-ethylenediamine.

The implementation of the glycide with the specified compounds can be carried out through. Accelerate the heating of the reaction mixture strongly, it is also possible to work in pressure vessels. It is also expedient to use clay catalysts, which have a catalytic effect, for example the hydroxides of the alkali or alkaline earth metals. Since the addition process is an exothermic process, it is often advisable to add part of the glycide to the reaction mixture and to use solvents or thinners. The Glycidmenge depends on the desired properties of the products ι they must in any case one EoI exceed the number of available reactive hydrogen atoms. In the case of raw materials that are sparingly soluble in water, it is advisable to apply a relatively large amount of glycide in order to achieve a product that is soluble or dispersible in water.

The solubility or divisibility of the compounds obtained in water can be largely changed or improved if the hydroxyl groups still present in them are etherified or esterified in the usual manner. To this Purposes can, for example, alkylene oxides or epichlorohydrin or inorganic or organic acids and their derivatives, such as Acid chlorides or acid anhydrides, organic sulfonic acids, such as 2-chloroethanesulfonic acid- (l), 1-chlorotoluenesulfonic acid-Ci), Ethene sulfonic acid, etc. can be used. When these reaction products sour Ua door own, can'Dian also in the form of her

Salts with synthetic or organic bases for use "bring.

Those obtainable by the process according to the invention Compounds can be used alone or in a mixture with one another or together with other cleaning, wetting, dispersing and solvents for the treatment and processing of materials of all kinds are used, e.g. as wetting, cleaning, Dispersing, emulsifying, impregnating and '.'. Calibrating agents in the textile, leather, rubber, lacquer and paper industries, as solvents and pasting agents and as protective colloids in the Dyeing and furthermore in the cosmetic and pharmaceutical industry for the production of ointments and creams.

It is known to react aromatic hydroxy compounds with alkylene oxides (German Patent No. 519 ^ J73O). Compared to the products obtainable by this known process, the new products obtainable by reaction with glycide show Products have the advantage of being soluble or distributable in water.

Example II

- 74 parts by weight of glycide are heated ^{to L0O-12O 0} with RjÄrokflusskühlung with the simultaneous addition of 1 part by weight of Eallauge and 0.5 parts by weight of sodium acetate. After a short time, with a sharp increase in temperature, the glycide polymerizes to give a dip-viscous oil which is clearly soluble in water. To achieve a higher polymerization stage and an even higher viscosity, another 182 parts by weight of glycide are added every year to the reaction mixture. The obtainable in this Yfeise polymerization is excellent as Scjaruxzkolloid in dispersing dyes yS

Büirch implementation of this product with oleic acid chloride or CopO oil fatty acid chloride become water-soluble products obtained as leveling or dispersing agent for dyeing # aer are useful.

- 4 example

74 parts by weight of isobutyl alcohol are placed in a stirred vessel and 1 part by weight of sodium hydroxide solution (33 ^ ig) under reflux cooling warmed to a gentle simmer. To this end, 148 parts by weight of glycid are slowly added dropwise, resulting in a viscous, pale yellow colored Cl, which is clearly soluble in water.

If a further 148 parts by weight of glycide are introduced into the reaction mixture in the same way, a higher viscosity product. The products obtained in this way are ideally suited as an additive to mercerising liquors to increase their wettability.

example % U

- In 68 parts by weight of prim.n-Undecylamine are under Addition of a little water at 60-80, 75 parts by weight of glycide were added dropwise with constant good stirring. The aqueous solutions The product obtained in this way foams strongly and is acid, lime and largely alkali-resistant. In a bath of 20 ° hard water, which contains 1 g of this product dissolved per liter, the cleaning effect for wool is excellent.

Example JL *

- 10 parts by weight of linoleic acid are at 60-100 ° in a pressure vessel with 12-14 parts by weight of glycide for several hours heated for a long time. The reaction product is an oily substance (acid number = 5 »6), which can easily be broken down into fatty glen and organic Solvents such as gasoline. With water it forms a thin, long-lasting emulsion. Linseed oil can be used in Presence of this product with turkish red oil is much easier emulsify than without this addition.

example

Z- To 25 parts by weight of coconut oil fatty acid If ^ -oxyethyl / amide and 0.5 parts by weight of sodium hydroxide solution (33%) are slowly added 75 parts by weight of glycide with reflux cooling at 140-150 °. The mixture is stirred at 150 ° for complete condensation for two more

Hours after it has cooled down, you get a viscous one rup, which dissolves easily and clearly in lasser. The watery one The solution foams strongly and has a good agitating and dispersing effect.

Claims (1)

Claim. Process for the preparation of water-soluble or dispersible condensation products, ^ dur ^ ch ^. ^ G indicates that one reactive organic compounds ^ * TCn which the reactive groups from one or more oxy and / or imino and / or carboxyl and / or carboxamide and / or There are sulfonic acid amide groups, with at least η 4- 1 mol of glycide converts, where η denotes the number of reactive hydrogen atoms present, and optionally those obtainable in this way Products etherified or esterified in the usual way. lM TO . L,. / irf ft [ψή J./tä-Si nt ^ s ftf