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United States Patent Office Patented Dec. 26, 1939. 2,185,163 UNITED STATES PATENT OFFICE 2,185,163 AMMONUM COM POLYOXYALKYLENEPOUNDS AND PROCESS OF PREPARING TEM Heinrich Ulrich, Ludwigshafen-on-the-Rhine, Germany, assignor to I. G. Farbenindustrie Aktiengesellschaft, Frankfort - on - the - Main, Germany No Drawing. Application July 21, 1936, Serial. No. 91,801. In Germany July 24, 1935 5 Claims. (C. 260-457) The present invention relates to the production dustries, for example as Wetting, cleansing, emull of polyoxyalkylene ammonium compounds and sifying and dispersing agents. Their usefulness process of preparing them. for the said purposes may be improved in many I have found that valuable nitrogenous con cases by employing them together with soaps or densation products i. e. polyoxyalkylene ammo substances having soap-like character or with nium compounds, are obtained by causing amine glue, gelatine or other organic colloidal sub oxides of tertiary amines to react at elevated stances, as for example Water-soluble varieties temperature in the presence of water, preferably of gun, vegetable mucilages or sulphite cellulose under superatmospheric pressure, with alkylene waste liquor, or with organic solvents, or with oxides, as for example ethylene Oxide, propylene two or more of these substances. In particular, 0 oxide, 1,2-butylene oxide, glycide, epichlorhydrine With the aid of the Said products Organic Sol and the like. The reaction, which may also be vents may be dissolved or emulsified in Water to carried out in the presence of organic solvents, a considerable extent whereby products are ob as for example low molecular aliphatic alcohols, tained which are suitable for example for wash acetone, diethyl ether, cyclohexanol and the like ing, bleaching and dyeing textiles, even in acid s 5 proceeds very readily. The condensation is car baths, and also for the dispersion of further Sub ried out for example by dissolving or distributing stances, They may also be employed, however, the said amine oxides in water or in one of the for stripping vat dyestuffs with the co-employ aforesaid solvents and causing the alkylene oxide ment of hydrosulphites. The unsulphonated con at a temperature 8bove 50° C., preferably ber densation products may also be employed with 3) 920 tween 90° and 10° C. to react with the amine advantage for the impregnation of fibrous ma oxides employed. f terials in order to increase their fastness to Amine oxides of tertiary amines suitable as Water. Furthermore the products also have a initial material in the present process are for ex more or less marked disinfecting action. ample trimethylamineoxide, triethylamine oxide, For many purposes it is advantageous subject tributylamine oxide, phenyl dimethylamine oxide ing the condensation products to the Sulphona 25 or p-tolyl-dipropyl amine oxide. Amine oxides tion. This may be effected by treating the COri containing a high molecular aliphatic radicle densation products with sulphonating agents particularly those containing an aliphatic radicle such as concentrated Sulphuric acid, oleum or with from 8 to 18 carbon atoms may be advan chlorsulphonic acid. The sulphonation may be 80 tageously employed as initial material. Such carried out at comparatively low temperatures, amine oxides are for example dimethyloctyl Such as from 5 below zero to 25° C. and while amine oxide, dimethyl dodecylamine oxide, di employing organic solvents, such as carbon tetra hydroxyethylcetylamine oxide, diethyl 9.10 chloride, either and the like, or while adding octodecenylamine oxide, methyl-didodecylamine water-binding substances for example phosphoric 35 oxide or methyl phenyloleyl amine oxide. acid anhydride or acetic acid anhydride. Prob The said amine oxides may also contain in the ably the sulphuric acid group enters into the free organic radicles, substituents such as halogen hydroxyl group on the end of the polyoxyalkylene atoms, carboxyl, ester, ether or hydroxy groupS. According to this process water-soluble prod radicle, thus for example products with the foll ucts are obtained which have an alkaline reac lowing constitution may be obtained: tion in contrast uo the initial materials which are R (CH-O)-SO3H N / entirely neutral. Presumably they possess the R-N following formula R, Yoh R (CH-O)-H 45 / (R1,R2 and Ra are organic radicles; a means the / N number of the oxyalkylene groups). R3 O After neutralization of the sulphonation prod wherein R, R2 and R3 stand for organic radicles uct with alkaline reacting substances such as and ac indicates the number of the oxyalkylene caustic soda solution, sodium carbonate, ammonia 50 groups contained in the polyoxyalkylene radicles or aliphatic amines, products are obtained which which are attached by oxygen to the nitrogen are easily soluble in water and which possess a atom. The products obtained according to this high washing and dispersing power. process may be employed with advantage as The following examples will further illustrat assistants in the textile, leather and lacquer in the nature of this invention but the invention is 55 2 2,185,168 not restricted to these examples. The parts are causing an amine oxide of a tertiary amine con by weight, taining at least one high-molecular aliphatic Eacample 1 radicle in the molecule to react at a temperature 90 parts of 63 per cent dimethyldodecylamine above 50 C. and in the presence of water with oxide containing water and 155 parts of ethylene ethylene oxide. oxide are heated in an autoclave at from 90 to 5. The process of producing nitrogenous con 100° C. until pressure is no longer detectable. densation products suitable as assistants in the The resulting condensation product is a syrup textile and other industries which comprises. 0 readily soluble in water, acids and alkalies; in causing a trialkylamine oxide containing at least aqueous and alcoholic solution it has an alkaline one aliphatic radicle with from 8 to 18 carbon O reaction. atoms in the molecule to react at a tempera Eacample 2 ture above 50° C. and in the presence of water 100 parts of a water containing 70 per cent with ethylene oxide. 5 amine oxide corresponding to the formula 6. The process of producing nitrogenous con densation products suitable as assistants in the 5 C N textile and other industries which comprises R-N=O causing an amine oxide of tertiary amines to react at a temperature above 50° C. and in the ch, presence of water with an alkylene oxide and 20 (R-alkyl radicle corresponding to the palm sulphonating the condensation product obtained. 20 kernel oil fatty acids) are dissolved in 100 parts 7. A nitrogenous condensation product suitable of water. Into the clear solution thus obtained 85 as an assistant in the textile and other industries parts of gaseous ethylene oxide are introduced which comprises essentially a compound contain between 90° and 100° C. The ethylene oxide is ing four organic radicles selected from the class readily absorbed and a clear aqueous solution of Consisting of aliphatic and aromatic radicles, at 25 a condensation product having a strong alkaline least one of which is a polyoxyalkylene radicle reaction is obtained. attached to a pentavalent nitrogen atom and a Eacample 3 hydroxy group attached to the nitrogen atom. 30 100 parts of an aqueous 70 per cent amine 8. A nitrogenous condensation product suitable as an assistant in the textile and other industries 30 oxide are as indicated in Example 2 caused to which comprises essentially a compound contain react with 200 parts of propylene oxide after ing four organic radicles selected from the class adding 200 parts of water at 90° C. in a closed consisting of aliphatic and aromatic radicles, at vessel until pressure is no longer detectable. In least one of which is a polyoxyethylene radicle this manner a viscose condensation product is attached to a pentavalent nitrogen atom and a 35 obtained which possesses a strong alkaline re hydroxy group attached to the nitrogen atom. action. 9. A nitrogenous condensation product suit Eacample 4 able as an assistant in the textile and other in 110 parts of trimethylamine oxide monohydrate dustries which comprises essentially a compound 40 are heated together with 200 parts of ethylene containing four aliphatic radicals at least one of oxide at from 90° to 100° C. until the whole which is a polyoxyethylene radicle attached to a d0 ethylene oxide employed has reacted with the pentaValent nitrogen aton and a hydroxy group amine oxide. The condensation product obtained attached to the nitrogen atom. is separated by filtration from some unaltered 10. A. nitrogenous condensation product suit trimethylamine oxide. It is a viscose mass having able as an assistant in the textile and other in a strong alkaline reaction. dustries which comprises essentially a compound The solution obtained is evaporated to dryness containing four organic radicles selected from the and the product obtained is dissolved in concen class consisting of aliphatic and aromatic radi trated sulphuric acid while maintaining a ten cles, at least one of which is a polyoxyethylene 50 perature of about 10° C. The sulphonation mix radicle attached to a pentavalent nitrogen atom ture is stirred for about 3 hours and then poured and a hydroxy group attached to the nitrogen onto ice. The solution thus obtained has a high atom and at least one of the organic radicles is a Washing and dispersing power. high molecular aliphatic chain. What I claim is: 11. A nitrogenous condensation product suit 55 1. The process of producing nitrogenous con able as an assistant in the textile and other in densation products suitable as assistants in the dustries which comprises essentially a compound textile and other industries which comprises caus containing four organic radicles selected from the ing an amine oxide of tertiary amines to react class consisting of aliphatic and aromatic radi at a temperature above 50° C.
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