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Publication numberUS2340881 A
Publication typeGrant
Publication dateFeb 8, 1944
Filing dateAug 22, 1939
Priority dateAug 22, 1939
Publication numberUS 2340881 A, US 2340881A, US-A-2340881, US2340881 A, US2340881A
InventorsMaurice J Kelley, Edwin A Robinson
Original AssigneeNat Oil Prod Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Composition for lubricating and softening textile fibers
US 2340881 A
Abstract  available in
Images(5)
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Claims  available in
Description  (OCR text may contain errors)

Patented Feb. 8, 1944 UNITED STATES PATENT OFFICE COMPOSITION FOR SOFTENING LUBRICATING AND TEXTILE FIBERS Maurice J. Kelley, Newark, and Edwin A. Robinson, Ohatham,

N. 3., asslgnors to National Oil Products Company, Harrison, N. J., a corporation of New Jersey No Drawing. Application August 22, 1939, Serial No. 291,34e

21 Claims. (CL 252-8.8l

sions thereof, the low water dispersibility of these amides renders them somewhat disadvantageous for use in this connection. While it has been proposed to solubilize amides of polyamines by treatment with acids, it has been found that in many cases the solubilization accomplished by such treatment i not sufficient to enable these amides to be successfully applied to textiles in the form of aqueous dispersions thereof.

It has also been, proposed to employ amides prepared by reacting monoethanolamine with fatty materials as textile lubricants and softeners; such amides, however, are also not as waterdispersible as might be desired. The use of textile lubricants and softeners comprising an amide of monoethanol triethylene tetramine has also been suggested; it has been found, however, that the employment of amides of this aminecauses objectionable yellowing of the textile fibers after the fibers treated therewith have been permitted to stand for a short period of time.

From the above discussion it will be evident that while a large number of fatty acid amides of various types have been suggested for use as textile lubricants and softeners, substantially all of these amides have the disadvantage of either being relatively non-dispersible in water or of causing objectionable yellowing of the textile fiber after the fiber has been permitted to stand for a short period of time. Therefore, there has been a constant demand for lubricants and softeners in the textile industry which do not possess either of the above disadvantages. As yet, however, this demand has not been satisfied.

It is the object of this invention to prepare textile lubricants and softeners which may be readily applied to textile fibers in the form of aqueous dispersions thereof, and which do not cause objectionable yellowing of the textile material even after prolonged standing. We have found that compositions comprising rial without causingany appreciable yellowing of the material even after prolonged standing. In

accordance with our invention textile lubricants:

and softeners are employed which comprise a fatty amide having the general formula moon-m-n-n A in which R1 denotes a fatty acidradical containing more than 5 carbon atoms; R: denotes an organic radical containing not more than 6 carbon atoms having an unsatisfied valence at both ends thereof and selected from the group consisting of straight chain hydrocarbon radicals, straight chain hydrocarbon radicals having a hydrogen atom replaced by a hydroxyl group, straight chain hydrocarbon radicals and straight chain hydrocarbon radicals having a hydrogen atom replaced radicals containing a keto grouping; A denotes a radical containing not more than 22 carbon atoms and selected from the group consisting of hydrogen, alkyl radicals, alkylol radicals, acyl radicals, and alkyl and alkylol radicals containing an ether or thio ether linkage; and B denotes a radical containing not more than 22 carbon atoms and selected from the group consisting of alkyl radicals, alkylol radicals, acyl radicals, and alkyl and alkylol radicals containing an ether or thio ether linkage, at least one of said R2, A and B radicals containing at least one hydroxyl group. The amides of our invention may easily be dispersed in aqueous media and the dispersions applied to textile fibers so as to give an excellent feel to the fibers without causing objectionable yellowing of the'fibers even after prolonged standing. The'preferred products of our invention are those having the general formula R1CONHCH2CH2-NHC2H4OH, since these products may be prepared from the readily available ethanol ethylene diamine, are readily dispersible in aqueous media and display particularly effective properties when employed as texa certain class of fatty amides may be applied HN-RzN-B i in which R2, A and B are as above defined, at

-ylaminodimethyl n-pentanol-3.

, also be reacted with amines of the above be reacted with an amine,

least one of said B2, A and B radicals containing at least one hydroxyl group, with a fatty acid containing more than carbon atoms or with a derivative thereof capable of reacting with amines to form amides. Thus, for example, the following amines have been found to be suitable for use in the preparation of the products of our invention: ethanol ethylene diamine, l-amino 3 methylamino isopropanol, N-ethyl N-ethanol ethylene diamine, N,N diethanol ethylene diamine, isopropanol ethylene diamine, l-amino 3-dimethylamino isopropanol, l-amino 2-ethyl 3-methylamino isopropanol, l-amino 2-ethyl 3-ethanolamino isopropanol and l-aminodimethyl 5-meth- We prefer to employ ethanol ethylene diamine in the practice of our invention since this amine is readily available and furnishes excellent water-dispersible textile lubricants and softeners when treated with fatty acids or their derivatives. It is to be understood, however, that other amines having the above generic formula may also be employed in the practice of our invention.

The fatty compounds with which the above amines may be reacted in accordance with our invention may be any fatty acid having more than 5 carbon atoms or a derivative thereof capable of reacting with amines to yield amides. Thus, for example, fatty acids such as stearic acid,-capric acid, oleic acid, coconut oil fatty acids or mixtures: thereof, and fatty acid derivatives such as olive. oil, coconut oil, cod oil, sperm oil, japan wax. methyl oleate and glyceryl monoor di-stearate may be employed to react with the amines. Naphthenic acids or their esters may type to yield amides suitable for use in accordance with our invention, and we intend to include such reaction products within the scope of the term fatty amides" since the properties of the naphthenic amides are entirely similar to the properties of the amides formed by reacting the mines with fatty acids or their derivatives. We

have found. that triglycerides of fatty acids containing more than 5 carbon atoms. e. g., coconut oil, teaseed oil. hydrogenated soy-bean oil and the like, react easily with the amines and yield amides having somewhat superior softening properties than those obtained by reacting the corresponding free fatty acids with the amines; hence we prefer to employ triglycerides of fatty acids having more than 5 carbon atoms as the fatty compounds reacted with the amines.

The reaction of the amine with the fatty compound may be carried out many suitable manner. The amount of fatty compound employed per mol of amine will vary depending upon the nature of the fatty compound used: thus it a fatty acid is to approximately equimolecular amounts of the acid and amine may be employed, whereas if a triglyceride such as coconut oil is used, approximately one-third of 8. mol of triglyceride per mol of amine may be employed. The temperature of the reaction may vary between about 100 C. and the boiling point of the amine, but preferably temperatures between about 125 C. and about 175 C. are employed. The reaction is preferably carried out at atmospheric pressure, but pressures below or above atmospheric may be used if desired. The reaction time may vary widely depending upon the particular ingredient employed; generally the reaction time will be between about 2 hours and about 48 hours. The products obtained from the reaction may be recovered in any suitable The fatty amides of our invention. may be applied to textilev materials in any sniiablema-nner.

Because of the fact that these amides are dis-' persible in aqueous. media, we have: found. it most advantageous; to apply these amides: to:- textile fabrics in thei'ormof aqueous dispersions: thereof.- These dispersions may be prepared in a variety of ways. We have: found; that: aqueous dispersions of the amides: of our invention are most advantageously prepared by mixing the: amide, preferably in liquid condition, with a dilute aqueous solution of an acid such as acetic acid, hydrochioric acid or lactic acid, whereby stable dispersions of the amides are formed immediately. dispersions. may containany suitable amount of the fatty amide. but;- we. prefer to: employdispersions containing'betweerr about 0.001% and about 5%; thereof; thus it wiltbea observed that dispersions containing. very small amounts of the amides ofour: invention arecapable of imparting. an excellent finish to textile fabrics. In many cases it may be desirable to prepare. relatively concentrated dispersionsofithe amide, e. g., dispersions containing 25% thereof, and then dilute. the dispersionsthus: prepared tothe desired concentration before. use; this method of preparing; the dispersions; is: advantageous when itis desired to store: or: ship the dispersionsprior to use. Textile:- i'abrics. treated with the amides of ourinvention show no objectionable yellowing even after prolonged periods of time.

It is to be understood that while it is preferred to apply the amides: of our invention to textile fabrics in the form of aqueous dispersions thereof, these amides maybe applied in any other suitable manner withoutv interferin with the excellent softness, pliabili'ty and drape which they impart to the fabrics.

The following. examples are illustrative of our invention.

. immersed in this dispersion for 10 minutes at a temperature of about 40 C. At the end of this time, the fabric was removed, squeeze-rolled, dried and ironed lightly. The fabric was. found and. drape, and did not yellow even after prolonged, standing.

Example I! 680 parts of coconut oil and 156 parts of ethanol ethylene diamine were mixed and the mixture heated at a temperature between about C. and about C. for 12 hours. A. light tan solid dispersible in water was obtained. This product was melted and hot water added thereto until an 0.015% dispersion of the amide was formed. This dispersion was then applied to rayon fabric as described in Example I, whereby a fabric was obtained having excellent softness and drape, and which did not yellow even after prolonged standing.

Example III 28 parts of oleic acid and 10 parts of ethanol ethylene-diamine were mixed and heated at a temperature between about 150 C. and about Amounts are given in parts: by weight.

1 170 C. for 12 hours. The resulting product was melted and 175 parts of a warm 4% acetic acid solution were added thereto. This solution was then diluted until an 0.015% dispersion of the amide was formed and this dispersion applied to rayon fabric as described in'Example 1, whereby a fabric was obtained having excellent softness and drape, and which did not yellow even after prolonged standing.

Example 1v 33 parts or castor oil and parts of ethanol ethylene diamine were mixed and the mixture heated to a temperature between about 150 C.

' and about 170 C. for 8 hours, whereby 'a yellow liquid was obtained. This liquid was mixed with 205 parts of a hot 4% acetic acid solution, and the resulting solution diluted so as to form an 0.015% dispersion of the amide. This dispersion was applied to rayon fabric as described in Example I, whereby a fabric was obtained hav ing excellent softness and drape, and which did not yellow even after prolonged standing.

Exampte V terpreted as illustrative and not 1.. a limiting sense.

Having described our invention, what'we claim as new and desire to secure by Letters Patent is".

1. A composition of matter comprising anamide which is the condensation product of a hydroxy-alkylated polyamine with a glyceride containing only substantially saturated non-hydroxylated fatty radicals.

2. A composition of matter comprising" an amide which is the condensation product of a polyamine of the type in which at least one of the amino groups contains a hydroxy-alkyl group, with a glyceride containing only substantially saturated non-hydroxylated fatty radicals.

3. A composition of matter comprising an amide which is the condensation product of v monoethanol-ethylene-diamine with a glyceride '74 parts of teaseed oil and 26 parts of ethanol ethylene'diamine were mixed and the mixture heated at a temperature between about 150 C. and about 170 C. for 8 hours. The product was a light tan solid. This product was melted and- 205 parts of a hot 4% acetic acid solution were added thereto. The resulting solution was diluted untilan 0.015% dispersion of the amide was formed. This dispersioirwas applied to rayon fabric. as described in Example I, wherebya fabric was obtained having excellent softness and drape, and which did not yellow even after prolonged standing.

Example VI 31 parts of hydrogenated soybean oil and 11 parts of ethanol ethylene diamine were mixed and the mixture heated at a temperature between about C. and about C. for 8 hours. The resulting solid was melted and 205 parts of a hot 4% acetic acid solution were added thereto. The solution thus obtained was then diluted until an 0.015% dispersion of the amide was formed.

- This dispersion was then applied to rayon fabric as described in Example 1, whereby a fabric was obtained having excellent softness and drape, and

which did not yellow even after prolonged standv ing.

It will be evident from the above description that our invention provides novel textile lubricants and softeners having properties which make them superior to lubricants and softeners heretofore employed. Therefore, our invention will be of great interest to those engaged in the finishing of textile materials.

The products of our invention may be further treated, if desired, to produce substances having desirable properties. For example, the amides may be sulfated or fosphated to yield wetting, dispersing and emulsifying agents, or they may be treated with acetic anhydride to yield products having excellent detergent and dispersing properties. Our novel products may also be treated in a variety of other manners known to the art so as to yield useful substances.

Since certain changes may be made in-the above products and different embodiments of the invention could be made without departing from the scope thereof, it is intended. that all matter contained in the above description shall be inethanol-ethylene-diamide with coconut oil glycerides.

'7. A composition of mat er comprising amides which are the condensatio products of monoethanol-ethylene-diamine with hydrogenated soyabean oil glycerides.

8. Acomposition of matter for lubricating and softening textile fibers consisting of an aqueous dispersion, in dilute acid solution, of an amide which is the condensation product of a hydroxyalkylated polyamine with aglyceride containin only substantially non-hydroxylated fatty radicals.

9. A composition of matter for lubricating and softening textile fibers consisting of an aqueous dispersion, in dilute acid solution, of an amide which is the condensation product of a polyamine of the type in which at least one of the amino groups contains a hydroxy-alkyl group, with a glyceride containing only substantially non-hydroxylated fatty radicals.

10. A composition of matter for lubricating and softening textile fibers consisting of an aqueous dispersion, in dilute acid solution, of an amide which is the condensation product of monoethanol-ethylene-diamine with a glyceride containing only substantially non-hydroxylated fatty radicals.

11. Compositions of matter for lubricating and softening textilefibers consisting of aqueous dispersions, in dilute acid solutions, of amides which are the condensation products of a hydroxy-alkylated polyamine with coconut oil glycerides.

12. Compositions of matter for lubricating and softening textile fibers consisting of aqueous dispersions, in dilute acid solutions, of amides which are the condensation products of a hydroxy-allgvlated polyamine with hydrogenated soyabean oil glycerides.

-13. Compositions of matter for lubricating and softening textile fibers consisting of aqueous dispersions, in dilute acid solutions, of amides which are the condensation products of monethanolethylene-diamine with coconut oil glycerides.

14. Compositions of matter for lubricating and softening textile fibers consisting of aqueous dispersions, in dilutei acid solutions, of amides which are the condensation products of monoethanolethylene-diamine with hydrogenated soya-bean oil glycerides.

15.- A composition of matter consisting of an aqueous dispersion, in dilute acid solution, of an amide which is the condensation product of a hydroxy alkylated polyamindwith a glyceride containing only substantially saturated, nonhydroxylated fatty radicals.

16. A composition of matter consisting of an aqueous dispersionyiin dilute acid solution, of an amide which is the condensation product of a polyamine of the type in which at least one of the amino groups contains a hydroxy-alkyl group,

' with a glyceride containing only substantially saturated, non-hydroxyiated fatty radicals.

17. A composition of matter consisting of an 20 aqueous dispersion, in dilute acid :solution, of an amide which is the condensation product of monoethanol-ethylene-diamine with a glyceride containing only substantially saturated, n onhydroxylated fatty radicals.

18, Compositions of matter consisting of aqueous dispersions, in dilute acid solutions, of amides which are the condensation products of a hydroxy-alkylated polyamine with coconut oil glycerides. Y

19. Compositions of matter consisting of aqueous dispersions, in dilute acid solutions, of amides which are the condensation products of a hydroxy-alkylated polyamine with hydro- I genated soyabean oil glycerides.

20. Compositions of matter consisting of aqueous dispersions, in dilute acid solutions, of amides which are the condensation products of monoethanol-ethylene-diamine with coconut oil glycerides.

21. Compositions of matter consisting of aqueous dispersions, in dilute acid solutions, of

amides which are the condensation products of monoethanol-ethylene-diamine with hydrogenated soyabean oil giycerides.

MAURICE -J. KELLEY. EDWIN A. ROBINSON.

CERTIFICATE or consscrron.

Patent n0; 2,5 i0,8e1.

musics J. KELLEY, ET AL.

February 8, 191414..

" It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows 3' Page 5, first column, line 61;, for "fosphated" read --phosphat ed--; line 52, claim 6, for "diamide" read --dianine-;

and second column, lines i 1 and 5 claims 8, 9 and lo'respectively, after "substantially" insert -satura ted--; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Ofri ce.

(Seal) si ed and sealed this 25th day of April, A. D. 191 h.

Leslie Frazer Acting Commissioner of Patents.

CERTIFICATE OF commoner. Pateot No; 215 40381. Febmary 8, 19M" mus cs J. KELLEY, m AL.

I It is hereby certified that error appears in the printed specification of the above n umbered patent requi ring correction as follows Page 5, first column, line 61;, for "fosphated" read --phosphat ed--; and second column, line 32, claim 6, for "diamide" read "(aminelines b5, 51 and 5 claims 8, 9on6. IO-respectively, after "substantially" insert "saturated"; and that the said Letters Patent should be read with this correction therein that the same may comom to the record 01 the case in the Patent 01- rice.

Signed and sealed this 25th day of April, A. 1). 191m.

Leslie Frazer (Seal) Acting Commissioner of Patents.

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2484146 *Apr 7, 1945Oct 11, 1949Houghton & Co E FLubricating composition
US2496776 *Feb 17, 1948Feb 7, 1950Eastman Kodak CoTextile yarns impregnated with lubricating compositions
US2690407 *May 25, 1951Sep 28, 1954Rca CorpMethod of preventing accumulation of static charges
US2806804 *Dec 29, 1952Sep 17, 1957Drew & Co Inc E FMethod of treating wool
US2842837 *Apr 17, 1956Jul 15, 1958United States Steel CorpMethod of working wire and a lubricant therefor
US2857330 *Dec 6, 1955Oct 21, 1958American Viscose CorpAnhydrous textile finishes
US2922707 *Feb 26, 1958Jan 26, 1960California Research CorpAmino amide salts of organic monocarboxylic acids as additives for reducing carburetor deposits
US2922708 *Feb 26, 1958Jan 26, 1960California Research CorpGasoline compositions
US2974022 *Aug 11, 1958Mar 7, 1961California Research CorpGasoline compositions containing phosphated amino amides
US2992994 *Jul 18, 1955Jul 18, 1961Ciba LtdDetergent composition for the hair
US3038820 *Mar 23, 1959Jun 12, 1962Ciba LtdProcess for imparting a soft feel to textile fibers
US3131147 *Jun 13, 1960Apr 28, 1964Ciba LtdProcess for imparting a soft handle to textile materials and aqueous dispersions suitable therefor
US3150941 *Feb 16, 1961Sep 29, 1964California Research CorpGasoline compositions containing mixtures of phosphates of amino alkylene amides
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US4786439 *Dec 22, 1987Nov 22, 1988Henkel Kommanditgesellschaft Auf AktienTextile treatment composition
US4865768 *Jan 14, 1987Sep 12, 1989Henkel Kommanditgesellschaft Auf AktienPhosphoric acid salt of the reaction product of a mono-carboxylic acid with a polyamine
US5318727 *Aug 14, 1991Jun 7, 1994Kao CorporationReacting cyclic amidine and/or acyclic amideamine with cationizing quaternary amine compound
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EP0213519A2 *Aug 16, 1986Mar 11, 1987Henkel Kommanditgesellschaft auf AktienTextile-treating composition
EP0307748A2 *Sep 5, 1988Mar 22, 1989Henkel Kommanditgesellschaft auf AktienFabric treatment composition
WO1992018685A1 *Apr 1, 1992Oct 29, 1992Henkel KgaaTextile treatment agent with improved water-dispersibility
Classifications
U.S. Classification252/8.61, 252/8.81, 516/69, 516/DIG.600, 554/55, 252/8.63, 252/8.86
International ClassificationD06M13/405
Cooperative ClassificationY10S516/06, D06M13/405
European ClassificationD06M13/405