Search Images Maps Play YouTube News Gmail Drive More »
Sign in
Screen reader users: click this link for accessible mode. Accessible mode has the same essential features but works better with your reader.


  1. Advanced Patent Search
Publication numberUS3664952 A
Publication typeGrant
Publication dateMay 23, 1972
Filing dateMay 15, 1970
Priority dateApr 3, 1967
Publication numberUS 3664952 A, US 3664952A, US-A-3664952, US3664952 A, US3664952A
InventorsMaske Bobby Charles
Original AssigneeAmerican Cyanamid Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Aqueous textile softening composition
US 3664952 A
A cationic textile finish composition for imparting softness to fibers, yarns, and fabrics, a composition containing a quaternary ammonium compound formed from the reaction of a fatty alkanol amine ester and a quaternizing agent and a polyoxyethylated fatty compound; a method for imparting softness to textiles using such a composition in the products obtained.
Previous page
Next page
Description  (OCR text may contain errors)

United States Patent Maske [451 May 23, 1972 [54] AQUEOUS TEXTILE SOFIENING COMPOSITION [72] Inventor: Bobby Charles Maske, Raleigh, NC.

[73] Assignee: American Cyanamid Company, Stamford,


[22] Filed: May 15, 1970 [21] Appl.No.: 37,875

Related US. Application Data [63] Continuation-impart of Ser. No. 627,672, Apr. 3,

1967, abandoned.

[52] US. Cl ..252/8.75, 117/1395 F, 117/1395 CQ, 252/87, 252/88, 252/89 [51] Int. Cl. ..D06m 13/46 [58] Field ofSearch ..252/8.8, 8.75, 8.7;

117/l39.5 F, 139.5 CQ

Primary ExaminerHerbert B. Guynn AttorneyChar1es .1. Fickey [57] ABSTRACT A cationic textile finish composition for imparting softness to fibers, yarns, and fabrics, a composition containing a quaternary ammonium compound formed from the reaction of a fatty alkanol amine ester and a quatemizing agent and a polyoxyethylated fatty compound; a method for imparting softness to textiles using such a composition in the products obtained.

5 Claims, No Drawings AQUEOUS TEXTILE SOFTENING COMPOSITION This application is a continuation-in-part of copending application, Ser. No. 627,672, filed Apr. 3, 1967, now abandoned.

The invention relates to a cationic textile finish and to the production therefrom of treated fibers, staple fibers, felts, threads, cords, yarns, pellicles, filaments, fabrics and the like of synthetic or natural origin, or blends thereof. More particularly, this invention relates to textile finishing compositions which impart softness to fibers, yarns and fabrics wherein the compositions are non-scorching when subjected to elevated temperatures, and non-yellowing.

The cationic textile softeners suffer from several disadvantages. Many of the cationic softeners are waxy or gummy in nature making them difficult to weigh or measure, to mix or disperse with other textile treating agents, and to place in a form, such as an aqueous dispersion, which may be readily applied to textiles. For these reasons, it is desirable to have a cationic softening composition capable of being effectively emulsified, having a high degree of storage stability, and capable of imparting both a softness of hand and a high degree of lubricity to the material being treated.

Softness is very frequently required in textile materials, particularly in fabrics used for clothing. The natural waxy, oily or fatty protective coatings of native fibers are often removed during the process of scouring and bleaching of these fibers. The fibers generally become harsh when these lubricants are removed, and fabrics formed from these fibers display an undesirable hand. In addition, certain coloring matters are prone to impart a dryness and an unpleasantness of hand to the fabric. Frequently, softeners are applied to fibers themselves to aid in the mechanical handling of these fibers since it is very difficult to spin any fiber from which the natural oils or waxes have been removed or, as in the case of man-made fibers, those which do notcontain ,a natural lubricant. Frequently, however, these treatments result in the production of a relatively stiff fabric which is harsh to the feel and less desirable commercially than fabrics possessing a soft hand. As a result, the industry has resorted to the use of several types of compounds for softening of finished fabrics and, in the case of rayon textile materials, for imparting thereto increased lubricity. The situations with which this invention is particularly concerned are those in which softeners are applied to yarn or fabric as a finish in themselves, to impart softness, smoothness, lubricity, fullness, suppleness, flexibility, and in some cases sewability as well.

There are a great many preparations available for softening textile materials and most, if not all, of these preparations are based on longchain fatty or waxy compounds. The watersoluble soaps appear in a great many of these preparations,

often for their softening properties as well as for their emulsifying properties. However, fabrics which include these soaps, which are soap-fat emulsions at their normal alkaline pH, exhibit a tendency to scorch when heated to the elevated temperatures encountered in certain textile processing operations. This tendency to scorch is apparently attributable to the presence of the soap or soap-like material. At the elevated temperatures encountered, the textile softening compositions containing fats or soaps become discolored or scorched thus marring the appearance of the fabric. Among compounds heretofore used have been the sulfonated hydrocarbons, waxes, stearates, and sulfonated oils, such as cotton seed oil, peanut oil, coconut oil and similar oil products. Additionally, in view of the competitive economics involved in the textile manufacturing field, some of the most widely employed softening agents have been sulfated or sulfonated tallow, and sulfated or sulfonated monoand diglycerides of the fatty acids of tallow, cotton seed oil, coconut oil, peanut oil and of other compounds containing the relatively long carbon chain of the higher fatty acids. The presence of these materials even in small amounts in cotton and rayon textiles has resulted in undesirable yellowing of the fabric subsequent to heating thereto.

Textile manufacturers do not find it economically expedient to treat only a portion of a particular lot of fabric for the scorch resistant textile finish. Furthermore, it is not known by the manufacturers how much or what part of a particular lot of fabric is to be subjected to elevated temperatures. Thus, it is desirable to have a heretofore unavailable composition capable of adequately being emulsified and capable of producing a softness of hand without the accompanying problems of being subject to scorching.

It should be noted that the adaptability of fibers, staple fibers, felts, cords, threads, yarns, pellicles, filaments, fibers, and the like to automatic handling operations is of extreme importance in the manufacture of textiles. Modern high speed machinery techniques require a feed of appropriate characteristics to permit uninterrupted and smooth operation. Accordingly, lubricity, softness, electro-static qualities, and the like, of the material being processed are intimately related to the performance of automatic mechanisms. Furthermore, the condition of the feed when it is subjected to the machine operations is likewise related to the excellence of the final product. For example, in the knitting industry, an improperly or poorly lubricated yarn produces uneven stitches. In the spinning of yarn, a minimal amount of lubrication is essential to the production of an even yarn, free of slubs. The problem is acute in the use of the more modern machinery, such as those employing the toe-to-top spinning process.

It is therefore an object of this invention to provide a textile softening composition suitable for use as a finish w which is resistant to scorching and yellowing, and characterized by a high degree of scorch resistance.

It is a further object to obtain a textile softening composition characterized by cationic components having excellent emulsion characteristics, having a high degree of fluidity, having a high degree of affinity for textile materials, and being readily dispersible with other textile treating agent, and which are cold water soluble.

Another object of this invention is to provide a textile softening agent which is abrasion resistant and which has good soil retardant properties. I

it is also a primary object of this invention to provide specially treated fibers, staple fibers, felt, cords, threads, yarns, pellicles, filaments, fabrics, and the like for the use in textile and related manufacture which possess combined characteristics of softness, lubricity, and antistatic properties which render them especially adaptable to machine handling.

An additional object is to obtain a process for making the composition of this invention.

The above objects are attained by the use of the composition of the invention which comprises (1) a fatty quaternary ammonium compound, (2) a fatty acid, (3) a polyethoxylated fatty compound, quaternizing (4) a stabilizing agent, in an aqueous solvent.

The fatty quaternary ammonium compound is the ester product formed by reacting one mole of a higher fatty acid with about one mole of an alkanol amine, and subsequently reacting with about one mole of a quaternizing agent, such as epichlorohydrin.

Suitable higher fatty acids for forming the fatty acid/alkanol amine ester are those having from about 12 to 22 carbon atoms such as stearic, arachidic, behenic, oleic, lauric, myristic, palmitic, and the like, and mixtures of such acids, such as from naturally occuring oils containing such acids.

The alkanol amines for forming the fatty acid/alkanol amine esters are generally alkylalkanolamines devoid of hydrogen atoms on the nitrogen atom wherein the alkyl radicals are lower alkyl radicals, such as dimethylethanolamine, diethylethanolamine, dimethylpropanolamine, methyldiethanolamine, and the like.

As indicated, the product of the fatty acid and alkanol amine is reacted with a quaternizing agent, e.g., epichlorohydrin, to form the fatty quaternary ammonium compound.

The quaternizing agent may be any well known in the art for quaternizing tertiary amino groups such as epichlorohydrin, or others such as diethyl sulfate, dimethyl sulfate, benzyl chloride, dodecylbenzyl chloride, methyl chloride, and the like.

Fatty acids found in the composition are in general the unreacted fatty acids from the reaction forming the fatty acid/alkanol amine ester. However, the fatty acid component found in the composition need not necessarily be the same as that used to prepare the fatty quaternary ammonium compound. This could occur where the reaction was carried to completion leaving no fatty acids, after which fatty acids of 12 to 22 carbon atoms could be added, if desired.

The fatty acid is a constituent of the preferred softening composition. However, in some compositions it can be omitted.

The polyethoxylated fatty compound is a polyethoxylated higher fatty amine, for example a polyethoxylated stearylamine, a polyethoxylated cocoamine, a polyethoxylated di-cocoamine, a polyethoxylated tallow-amine, and the like; higher fatty amide, for example a polyethoxylated stearamide, a polyethoxylated oleamide, a polyethoxylated hydrogenated tallow-amide, and the like; and a polyethoxylated higher fatty acid, for example a polyethoxylated stearic acid, a polyethoxylated oleic acid, a polyethoxylated coco fatty acid, and the like. All of the polyethoxylated fatty compounds contain between and 60 moles of ethylene oxide per mole of fatty compound.

The stabilizing agent is, for example, a 25 percent solids aqueous mixture of formaldehyde (40 percent of the solids) and sodium bisulfite (60percent ofthe solids).

The composition of the invention is obtained by admixing the components in the amounts by weight as follows: fatty quaternary ammonium compound ranging from about 8 to 24 parts, preferably 17 to 21 parts; fatty acid ranging from about 0 to 8 parts, preferably 0 to 4 parts; polyethoxylated fatty compound ranging from 0.5 to parts, preferably 2 to 5 parts; stabilizing agent ranging from 0 to 7 parts, preferably 0 to 3 parts; and sufficient water to form a composition having a preferred 25 percent solids content. The water may of course be adjusted from 5 to 95 to obtain a different solids content maintaining the relative ratios of the other ingredients. Thus a paste or a solid might be formed.

A particularly preferred composition is formed from (1) stearoylethyl dihydroxypropyl dimethyl ammonium chloride, (2) stearic acid, (3) an adduct of 50 moles of ethylene oxide and stearylamine, and (4) a 25 percent solids aqueous solution of formaldehyde and sodium bisulfite, and water.

The composition may be applied to textiles from aqueous solution on conventional textile processing equipment by either the padding or spraying method, or by the exhaust method from a long bath, at concentrations such as to deposit the desired percent on the fibers, for example at l to 2 percent concentrations.

Both the characteristic of the finishing composition, as well as an advantage over prior compositions, is a low viscosity, characteristically a viscosity as low as about 19 centipoises at about 25 percent solids, and a very small particle size, substantially all particles being of a particle size below about 1 micron, to give superior penetration of fabrics by the softening particles.

When the above composition is applied to textile material such as cotton, or a blend of cotton, or any of the other textile materials discussed above as within the scope of this invention, a textile material is formed having improved properties characterized by softness of hand and a lubricity as discussed above.

Also, by the employment of the above composition as defined, a highly desirable and workable process for applying said composition to textile materials results from the highly emulsified composition in the aqueous solvent, which ordinaryily is only water.

In addition, by the employment of the above composition of this invention, the problems of poor stability have been substantially overcome.

it should be noted that an advantage of the composition of this invention lies in the ability to obtain a uniform softening of the yarn, as a result of the even distribution obtainable from the high quality emulsion of particles less than 1 micron in size. Another advantageous characteristic of the finishing composition of this invention is that it is completely soluble in cold water, as well as warm water, thereby allowing it to be mixed at room temperature without bothersome, expensive, and time consuming heating up to obtain solution. The finishing composition resists both yellowing and odor development, and is non-chlorine retentive. Additionally, it is possible to have solids content which is characteristically higher than the normal solids content for a cationic liquid textile softener of this type, thereby resulting in a savings to the customer since the customer will be shipped more real product and less water. Additionally, the product is very fluid, the viscosity thereby permitting easy pumping, metered measuring out of bulk storage, and no substantial change in viscosity between temperatures of about 40 and 100 F. The finishing composition of this invention is a cationic textile softener which can be used in thermosetting resin formulations, or as a pure finish to provide soft handle and lubrication to fabric or yarn which may thereby process enhances physical properties such as better draping qualities, better resistance to abrasion, reduced needle cutting, and the like.

The following examples are given to illustrate the invention disclosed herein, and are not intended to be limitative.

EXAMPLE I A composition was prepared having the following parts by weight:

Stearoylethyl dihydroxypropyl The composition of the mixture can be varied slightly by changing the amount of Ethomeen 18/60 and Stabilizer 795.

Ingredient No. 1 is the reaction product of stearoylethyl dimethylamine and epichlorohydrin. Ingredient No. 2 is the unreacted stearic acid which remains in the stearoylethyl dimethylamine synthesis. Ingredient No. 3 is the adduct of 50 moles of ethylene oxide and stearylamine. Ingredient No. 4 is a 25 percent solids aqueous solution of formaldehyde and sodium bisulfite.

The product is made by first reacting one mole of dimethylethanolamine with one mole of stearic acid, removing the water of reaction by azeotropic distillation with toluene at 120 to 130 C. The reaction is considered complete when the free fatty acid content reaches 19 percent at which time the toluene is stripped under vacuum at to 1 10 C. and the intermediate stearoylethyl dimethylamine is isolated as a very soft, low-melting, straw-colored solid.

In the second stage reaction, the stearoylethyl dimethylamine is mixed with the water and reacted at to C. with epichlorohydrin to obtain the dihydroxypropyl derivative which is the cationic quaternary ammonium com pound desired. Ethomeen 18/60, which aids fluidity and cold water dispersibility, and Stabilizer 795 to inhibit possible yellowing and to augment fluidity are added to the reaction mixture. The moisture content is adjusted to 74 :t 1.0 percent and the product is drummed. The product is an off-white coldwater soluble liquid.

Example I represents a preferred embodiment of the invention.

EXAMPLE II A composition was prepared according to Example I having the following parts by weight:

Quaternary ammonium chloride (Reaction of mixed arachidic-behenic acids with a stoichiometric amount of dimethylethanolamine and with An off-white cold-water soluble liquid was formed.

EXAMPLE III A composition was prepared according to Example I using ingredients in the following parts by weight:

Fatty alkanolamine (Product of mixed behenic-arachidic acids with a stoichiometric amount of dimethylethanolamine) 160 Epichlorohydrin 42 Ethomeen l8/60 30 Stabilizer 795 16 Water 600 A cold-water soluble off-white liquid was obtained.

EXAMPLE IV hydrogenated tallow fatty acid) 5 Stabilizer 795 2 Water 80 The final product formed was an off-white, cold-water soluble liquid.

EXAMPLE V Fatty alkanolamine (as in Example III) 40 Dodecyl benzylchloride 30 Stabilizer 795 0.5

Water This final product formed a white, difficulty cold-water soluble paste.

EXAMPLE VI Fatty alkanolamine Epichlorohydrin 5 Arquad 1 8-50 10 Stabilizer 795 3 Water The fatty alkanolamine intermediate was prepared by reacting mixed palmitic-stearic acids with dimethyl ethanolamine. Arquad 8-50 is a 50 percent solution of steryl trimethyl ammonium chloride from Armour Industrial Chemical Co. This final product formed a thick, white paste. Arquad 2C-50, (Armour Co.), a 50 percent solution of dicoco-dimethylammonium chloride, and Ethoquad 18/25, (Armour Co.), the product of stearylamine and 15 moles of ethylene oxide uaternized with methyl chloride, were used in this same formu ation. The

final product was again a paste.

It is within the scope of the invention to prepare the fatty quaternary ammonium compounds by other methods, for example by reacting methyl stearate and dimethylanolamine and collecting methanol as a by-product instead of water, although this method may not be as economical as that of Example I.

While I have set forth certain specific examples and preferred modes of practice of the invention, this is solely for the purpose of illustration, and it will be understood that various changes and modifications may be made in the invention without departing from the spirit of the disclosure or the scope of the appended claims.

I claim:

1. An aqueous textile softening composition consisting essentially of:

a. from about 8 to about 24 percent of a fatty quaternary ammonium compound which is the ester formed by reactmg:

l. a higher fatty acid having from about 12 to 22 carbon atoms;

2. an alkanolamine selected from the group consisting of dimethylethanolamine, diethylethanolamine, dimethylpropanolamine and methyldiethanolamine; and

3. a quaternizing agent selected from the group consisting of epichlorohydrin, diethyl sulfate, dimethyl sulfate, benzyl chloride, dodecylbenzyl chloride and methyl chloride;

b. from about 0 to about 8 percent of a higher fatty acid C12 'C22 and c. from about 0.5 to 15 percent of an ethoxylated fatty amine wherein said fatty amine contains between 10 and 60 moles of ethylene oxide per mole of fatty compound.

2. The composition of claim 1 wherein the amount of water is about 74 percent.

3. A composition according to claim 1 further containing from about 0 to about 7 percent of a stabilizer consisting of an aqueous solution of formaldehyde and sodium bisulfite.

4. The composition of claim 3 consisting essentially'of in parts by weight (a) 18.7 parts stearoylethyl dihydroxypropyl dimethyl ammonium chloride, (b) 3.3 parts stearic acid, (c) 3.5 parts ethoxylated stearylamine, (d) 0.5 parts of a 25 percent solids aqueous solution of formaldehyde and sodium bisulfite, and (e) 74 parts water.

5. A softened textile material which has been treated with the softening composition of claim 1.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2160458 *Oct 31, 1935May 30, 1939Du PontArtificial thread dressing composition
US2205042 *Oct 26, 1937Jun 18, 1940Du PontSoftening of textile materials and compositions therefor
US2213673 *Oct 25, 1937Sep 3, 1940Ninol IncTreatment of textiles
US2862009 *Feb 24, 1955Nov 25, 1958Ciba LtdNew water soluble quaternary ammonium salts
US3091552 *Apr 28, 1961May 28, 1963Courtaulds LtdProcess for increasing the resistance of polyacrylonitrile fibers to discoloration
US3154489 *May 28, 1962Oct 27, 1964Armour & CoSurface active compositions
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3973065 *Jan 10, 1975Aug 3, 1976Microfibres, Inc.Synthetic suede
US4085245 *Apr 15, 1976Apr 18, 1978Xerox CorporationTransparencies for color xerographic copies
US4238373 *Mar 5, 1979Dec 9, 1980The Procter & Gamble CompanyProcess for making detergent compositions containing nitrogenous cationic surfactants
US4446032 *Feb 11, 1982May 1, 1984International Flavors & Fragrances Inc.Liquid or solid fabric softener composition comprising microencapsulated fragrance suspension and process for preparing same
US4464271 *Nov 30, 1983Aug 7, 1984International Flavors & Fragrances Inc.Liquid or solid fabric softener composition comprising microencapsulated fragrance suspension and process for preparing same
U.S. Classification428/375, 252/8.63
International ClassificationD06M13/372, D06M13/432, D06M13/00, D06M13/224, D06M13/463
Cooperative ClassificationD06M13/224, D06M13/463, D06M13/372, D06M13/432
European ClassificationD06M13/372, D06M13/224, D06M13/463, D06M13/432