UNITED STATES PATENT of FICE 2,345,632 POLAM DES ) Edwin A

Patented Apr. 4, 1944 2,345,632 UNITED STATES PATENT OF FICE 2,345,632 POLAM DES ) Edwin A. Robinson, Chatham, and Maurice J. Kelley, Newark, N.J., assignors to National Oil Products Company, Harrison, N.J., a corpora tion of New Jersey N. No Drawing. Application May 20, 1939, serial No. 274,808 13 Claims. (CL 260-404.5) This invention relates to textile lubricants and vide a process for the preparation of textile softeners, more particularly to textile lubricants lubricants and softeners from polyamines. and softeners comprising mixed fatty polyamides. We have now found that polyamides having It has been proposed to use higher fatty the general formula R1CO-NR3-X-COR2 in amides, such as oleic acid amide, oleic acid which R1 stands for an alkyl radical containing methyl amide and oleic acid ethylene diamide from 7 to 21 carbon atoms, Ra stands for an alkyl as Softeners and lubricants for textile materials. radical containing from 1 to 4 Carbon atoms, ER3 Such amides are ordinarily prepared by reacting stands for hydrogen or an acyl group containing a fatty acid or fatty ester with a mono- or poly from 2 to 5 carbon atoms and X stands for the amine. The reaction of monoamines with higher O grouping (CRR-CR-R-NR) , Wherein R4 fatty acids or fatty esters yields products which and R5 stand for hydrogen or alkyl radicals, and n. are not readily dispersible in water, and since is a whole number, may be applied to textile these products contain no residual amino group, materials so as to impart thereto excellent soft they may not be solubilized to any substantial ness, drape and pliability without causing yellow extent by treatment with acids. Hence these s ing of the material. The preferred polyamides products may not be advantageously applied to of our invention may be prepared in a simple textile material. It has been proposed, there and inexpensive manner by reacting a readily fore, to react polyamines with higher fatty acids available polyamine such as ethylene diamine, or fatty esters to produce amides having free diethylene triamine, triethylene tetramine, etc., amino groups capable of reacting with weak 20 with a fatty acid containing from 8 to 22 carbon acids so as to solubilize the products and render atoms or an ester thereof, and with a short chain them readily dispersible or soluble in water. fatty acid containing from 2 to 5 carbon atoms However, the monoamides formed from such or an ester, anhydride or acid halide thereof. polyamines, by reaction thereof with higher fatty Preferably, the polyamides of our invention con acids or fatty esters cause yellowing of textile 25 tain one secondary amino group so that they material upon application thereto, and hence may be treated with weak acids for the produc are highly unsuitable for use as textile lubri tion of Solubilized modifications of the poly cants and softeners. On the other hand, poly amides. We have found that the presence of amides formed by the reaction of higher fatty substantially more than one secondary amino acids Or fatty esters with polyamines are much 30 group in the polyamides of our invention tends less desirable as Softeners and lubricants than to cause objectionable yellowing of the textile the corresponding monoamides because of their material to which the polyamide is applied; relatively poor softening and lubricating proper hence, if polyamines containing more than 3 ties. nitrogen atoms, e. g., triethylene tetramine ol 5 tetraethylene pentamine, are employed to pre It has also been proposed to prepare textile pre the products of our invention, preferably lubricants and softeners by reacting unsym stifficient amounts of the short chain fatty acid metrical dialkyl ethylene. diamine with higher are employed so as to acylate all but one of the fatty acids such as oleic acid. Such unsym Secondary amino groups. metrical dialkyl annines are, however, relatively 40 The products of our invention are preferably expensive and diffic lit to obtain, and hence, while prepared by reacting a polyamine with a higher the amides thereof have been used to some ex fatty acid containing from 8 to 22 carbon atoms, tent as textile lubricants and softeners, there is preferably from 12 to 18 carbon atoms, or an a great demand in the textile industry for ester thereof so as to form a monoamide, and cheaper products which may be used in place 46 then reacting the monoamide with suitable of these annides. amounts of an acid containing from 2 to 5 carbon It is the object of this invention to provide atoms. However, when employing diamines or inexpensive and highly effective textile lubri triamines in the practice of our invention, the cants and Softeners, s preparation of the amides may be carried out It is a further object of this invention to pro 50 by first reacting the polyamine with the short 3,868,682 chain acid and then seating he product with to 5 carbor atois; as above mentioned, anhy 3.he long chain fatty acid. Any polyainine may dides, ester's or acid halides of these acids may ise used in the practice of our invention; thus, also be employed. The amount of short chain for example, polyai initias Such as ethylene dis acid compound employed depends to gone extent anize, diethylene tria Raine, tiethyiene tetrae s upon the number of amino groups to be acylated mine, tetra ethylene pentainine and hydroxy and the Eaature of the compound used. Thus in ethyl ethylene die nine may be employed. We the case of diethylene triainine, we prefer to en prefer to use diethylene trianine since we have pioy about inol of a short chain fatty acid per found that aridies prepared from this polyamine mol of diethylene triarmine; however, in the case in accordance with our invention are highly of triethylene tetramine, where it is desired to affective textile lubricants and softeners, do not acylate not only the -NHa group but also one of yellow textile materiai to which they are applied the secondary amino groups, approximately 2 mols and may be readily Solubilized by treatment, with of the short chain acid per mol of the polyamine weak acids; furtheriore, diethylene trainine is may be employed. It is to be understood that if relatively inexpensive and readily available, derivatives of the short chain acid are reacted The long chain fatty acid compound reacted with the monoamide, the amounts thereof will be with the polyamine in accordance with our in - adjusted accordingly; for example, approximately vention may be any of the fatty acids contain one-half no of acetic anhydride is used where iing from 8 to 22 C&rbon atoms, preferably from 12 one mol of acetic acid is required. If desired, Sufi to i8 carton atons, or the esters thereof; the foll cient amounts of the short chain acid may be used ioning higher fatty acids may be entioned by so as to form two amido groups on the free -NH2 way of examples: caprylic acid, nonyi ic acid, group; the -NH-group adjacent the long chain capric acid, undecylic acid, lauric acid, syristic fatty group may also be acylated. Generally, &cid, palnitic acid, searic acid, behenic acid, it may be said that the number of nois of short oleic acid, ricinoleic acid, mixtures of these acids; 25 chain fatty acid employed per inol of polyamine etc. In place of the higher fatty acids, tieriva will be equivalent to the number of groups to tives thereof such as glycerides &nd other esters, be acylated in accordance with or invention. Inay he employed. Actually, we prefer to use The conditions under which this reaction is car glycerides of the fatty acids since products are tied out may Vary widely, but we have found the 8, obtained having Stiperior softening properties to the constituents may be reacted at atmospheric those resulting from the reaction of the poly. pressure and at a temperature of about 135 C. anines with the free fatty acids. Products par for about 3 to 5 hours, the mixture then raised ticularly suitable as textile lubricants and soft to between about 50 C. and about 170° C., and eners are obtained by employing coconut, oi! to the reaction continued for about 5 to about 8 addi react with the polyamines in accordance with our 35 tional hours with excellent results. However, it is invention, since these products are dispersible in to be understood that these conditions may be Water Without ifurther Solubilizing Greatment, and varied somewhat, without affecting the course of possess excellent lubricating and softening prop the ireaction, e.g., pressures above or below at eries. As ex82nples of other glycerides that may nospheric may be used, the temperatures may be employed is place of the long chain fatty acids, Very widely so long as they are sufficiently high to there may be mentioned teaseed oil, eastor oil, effect, acylation, and the time of reaction may hydrogenated eastor oil, etc. differ from the time above set forth. he short, chain acidis employed in accordiance The products of our invention ay be liquids of with our invention contain from 2 to 5 caron soids, but generally they are solids. The ins atoms; this, for example, acetic acid, actic acid, jority of these products are relatively insoluble propioic acid, butyric scid and valleric acid may in water; however, products somewhat soluble be exployed; derivatives hereof such as esters, or dispersible in water may be obtained. As above acid halides and 8.nihydrides Ray See eployed in sentioned, the coconut oil products are generally ScCordiance with procedures well known to the dispersible in water.

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