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United States Patent ‘ Patented Mar r 2,786,869 United States Patent ‘ Patented Mar. 26, 1957 l 2 tically, mixtures of tert-alkylamine such as are available on the market. Typical mixtures are those containing ‘ 2,786,869 C12H25NH2 to C15H31NH2 or C18H3'INH2 to C24H49NH2 N-TRIALKYLCARBINYL-N-(HYDROXYETHYL or C15H31- to C24H49NH2. These may be represented by POLYOXYETHYL) GLYCINES the formula Peter L. de Benneville and Homer J. Sims, Philadelphia, 31 Pa., assignors to Rohrn & Haas Company, Philadelphia, R’-—-C—NH2 Pa., a corporation of Delaware Rs No Drawing. Application June 16, 1954, 10 As catalysts in the ?rst step of the process of this Serial No. 437,273 invention, wherein the hydroxyethyl group is introduced, 9 Claims.‘ (or. 260-534) there may be used any of the strong acids, such as hy drochloric, hydrobromic, sulfuric, arylsulfonic, alkanesul fonic, or phosphoric. The preferred amount of this cat This invention relatesto-compounds of the structure 15 alyst is 10 to 30 mole percent of the amine. With R1 '(CH2CH2O),.H ‘ , amines from 12 carbon atoms upward it is exceedingly di?icult to introduce more than one hydroxyethyl group in a tert-alkylamine molecule. Such amines‘yicld ?nal 3 \CHrCOOH products which have the desired balance of properties. ' wherein R1, R2, and R3 are alkyl groups containing a 20 The ?rst reaction with ethylene oxide is effected by total of 11 to 23 carbon atoms and n is an integer having bringing together ethylene oxide and tert-alkylamine, a value from 5 to about 50 or more, preferably 5 to 25. usually by passing ethylene oxide into amine and catalyst, These compounds may be called N-(trialkylcarbinyl)-N at temperatures from 0° to 180° C. The preferred tem (hydroxyethylpolyoxyethyl)glycines or N-carboxymeth peratures for reaction are between 60?’ and 95° C. yl-N-trialkylcarbinylaminopolyethoxyethanols. ‘ 25 Upon addition of one mole of ethylene oxide per mole As these names suggest, these compounds are poly of a said tert-alkylamine in the presence of an acid cat ether alcohols and glycines. They possess in ‘addition alyst reaction ceases. The acid catalyst is then de to the ether chain which‘ confers marked polarproperties stroyed, as by adding a base. Sodium or potassium hy a zwitter-ion which can react with either acids or bases droxide, sodium or potassium carbonate, or calcium hy to form :salts and thereby change the surface active char droxide may be used for this purpose. A concentrated acteristics of the compounds. In contrast to the usual aqueous alkali solution may be used and the resulting non-ionic surface active agents, these compounds supply aqueous layer is drawn off. If an aqueous solution is not anti-corrosive action. They confer anti-static properties used, the sludge or salt which forms is ?ltered off. The to plastic surfaces, including the surfaces of synthetic reaction mixture is then stripped of any remaining water, ?bers. They are preferentially absorbed on various 35 as by heating under reduced pressure. This step is solids, including pigments, ores, and other minerals and necessary to avoid formation of polyethylene glycols in can thus assist in classi?cation, ?otation, dispersion, and the subsequent reaction. adhesion. They can be used as anti-foam agents, as in In the next stage of reaction the monohydroxyethyl paper manufacture. They have bactericidal and fungici compound is treated with 0.5 to 5 mole percent of an dal properties. They can be used as emulsi?ers and as 40 alkaline catalyst and with ethylene oxide in an amount deemulsi?ers. They are effective wetting agents in many to give the particular kind of product required. Sodium textile and paper applications. Also, the compounds of. hydroxide or potassium hydroxide provide good catalytic this invention can be incorporated into plastisols and action, but alkali metal alcoholates, such as sodium meth organasols to reduce the viscosity thereof. 45 oxide or potassium butoxide may also be used. The re The compounds of this invention can be considered to action may be run under ordinary or elevated pressures. be derived from tert-alkylamines through an interesting A pressure of 10 to 20 p. s. i. provides a rapid‘rate‘of series of reactions which are eifective because of the reaction at temperatures from 100° to 200° C. The pre peculiar nature of the trialkylcarbinyl group in its rela ferred range is 130° to 170° C. \ tionship to the rest of the molecule. The course of re 50 When four or more units of ethylene oxide have been action is also determined by the size of the trialkylcar taken up at this stage per molecule of hydroxyethylated binyl groups used, these being of 12 to 24 carbon atoms. tert alkylamine, ?nal products are obtained which are With this particular kind of group of the de?ned size the water-soluble. As the number of ethoxy groups increases ?rst stages of reaction lead to the introduction of a poly above four, improved solubility and increased polarity > are observed. The products can thus be adjusted to give i ethoxyethanol group replacing only one of the two hydro 55 gens on the nitrogen of the primary amine, RN'I-Iz, al an optimum effect for any speci?c application. I though it would appear that both are of equal value and Details of typical procedures for preparing the l activity. Two steps are required to introduce a poly RNH(CH2CH2O)71.H 1 ethoxyethanol group, the ?rst giving an N-hydroxyethyl compounds are given in the following section. t compound and the second carrying this compound to 60 i the polyethoxyethanol. When the polyethoxyethanol PREPARATION A group has been introduced, giving compounds of the There were mixed in a reaction vessel equipped with formula RNH(CH2CH20)1LH, these compounds are re stirrer, thermometer, and inlet tube 286 parts of a techni acted with formaldehyde and hydrogen cyanide or the cal tert-octadecylamine, which comprised chie?y C18 equivalent thereof, to give monocyanomethylated prod 65 amines with some higher tert-alkyl primary amines, and ucts, RN(CH2CH) (CH2CH2O)nH. These are now sub 28.6 parts of aqueous 35% hydrochloric acid. The mix jected to hydrolysis with an aqueous alkali metal hydrox ture was stirred and heated to about 90° C., whereupon ide solution and the resulting salt separated or converted ethylene oxide was introduced through the inlet tube. to the acid form, RN(CHZCOOH)(CH2CH20)1LH The temperature was held at 90°-94° C. and the pres As, trialkylcarbinylamines there may be used any of 70 sure at one to ?ve pounds gauge until 44 parts of ethylene the primary N-tertiary alkylamines having 12 to 24 car oxide had been added. The water was then taken off bon atoms. Single entities may be used or, more prac under reduced pressure and about 200 parts of aqueous 2,786,869 5%‘v sodium hydroxide'isolution added. The water layer No. 371,194, ?led by Gerard C. Riley on July 29, 1953, was taken off and a second 200 part portion'of 5%- so the‘ assignment'of' which is‘ in-the‘hands'of'a- common dium hydroxide added and then separated. The washed assignee. Suf?cient of the disclosure has been here in oil was stripped under low pressure and ?ltered to give troduced to give a clear and complete exposition of the 3'30‘~parts of‘aiclear‘redv oil. This‘ had a neutral equiva preparation of the tert-alkylaminopolyethoxyethanols lentiof132‘6', thus ‘corresponding essentially to'N-hydroxy which are required for the preparation of the glycines of ethyl-tert-octadecylamine, the theoretical'netural equiva~ this invention. lent being 330. After a tert-alkylaminopolyethoxyethanol has" been A portion of 99 parts of this oil was treatedlwith 0.3 formed, it is reacted with formaldehydeand hydrogen part of potassium hydroxide: There was added thereto 10 cyanide, thus over a period of four hours 132~parts of ethylene oxide RNH(GH2GH2O),.H-+;HOHO + HCN~‘-—-+ with the temperature held at 160°—170° C. at one to ?ve pounds pressure (gauge). The reaction mixture was treated. with;1;3 parts of; 20% sulfuric, acid, stripped, andi?ltered. ' 15 The order in which these reactants are mixed or com The ?nal product wasaiclear red oil which was soluble bined is not critical. Excess formaldehyde and hydrogen in water to. giVeFsUrfa‘ce active solutions and which cor cyanide are permissible and may be supplied to the re responded;inicompositio'nlto‘ action mixture as separate reactants. Again, the tert alkylaminopolyethoxyethanol may be- ?rst‘ treated‘ with tei'f-CiaH1'zNH'( CH2‘CH20) roCHzCI-IQOH - 20 formaldehyde, asfrom the aqueous solutions of com PREPARATION B merce and hydrogen cyanide then added as liquid or gas A technical mixture of"trialkylcarb'inylamines' from at temperatures from 0° to 50° C. or more. It is more C18 to Czt‘having'a‘neutral equivalent of 360 was re convenient, however, to react formaldehyde and cyanide acted'as in Preparation‘ A with‘ a molarproportion of in a separate step to-form glycolonitrile and this ethylene oxide. There‘ was thereby, formed an N-hy 25 with the tert-alkylaminopolyethoxyethanol. This reac-~ droxyethyl-tert-carbinylamine having a neutral equivalent tion may be carried out in water or an alcohol-water of ‘405, a density at 50° C. of 0.865, and a congealing mixture at temperatures of about 20° to 100° C. The temperature of —15° C. glycolonitrile may be formedby-reacting-formaldehyde Portions of this product were taken and reacted as and hydrogen cyanide or an alkali'metal cyanide'and. above with various‘ proportions of ethylene oxide to give acid; asiis known. tert-carbinylaminopolyethoxyethanols.> Reaction in the Thev N - cyanomethylated tert - alkylaminopolyethoxy proportion of one mole, of N-hydroxyethyl-tert-carbinyl ethanol is? now hydrolyzed.
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