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US3664952A - Aqueous textile softening composition - Google Patents

Aqueous textile softening composition Download PDF

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Publication number
US3664952A
US3664952A US37875A US3664952DA US3664952A US 3664952 A US3664952 A US 3664952A US 37875 A US37875 A US 37875A US 3664952D A US3664952D A US 3664952DA US 3664952 A US3664952 A US 3664952A
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United States
Prior art keywords
composition
parts
percent
fatty
textile
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US37875A
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English (en)
Inventor
Bobby Charles Maske
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Wyeth Holdings LLC
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American Cyanamid Co
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/372—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core

Definitions

  • 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.
  • 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.
  • certain coloring matters are prone to impart a dryness and an unpleasantness of hand to the fabric.
  • 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.
  • Another object of this invention is to provide a textile softening agent which is abrasion resistant and which has good soil retardant properties.
  • An additional object is to obtain a process for making the composition of this invention.
  • 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.
  • 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.
  • a quaternizing agent e.g., epichlorohydrin
  • 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.
  • 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).
  • 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.
  • 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.
  • a 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.
  • compositions 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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 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.
  • 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
  • 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.
  • An aqueous textile softening composition consisting essentially of:
  • alkanolamine selected from the group consisting of dimethylethanolamine, diethylethanolamine, dimethylpropanolamine and methyldiethanolamine;
  • a quaternizing agent selected from the group consisting of epichlorohydrin, diethyl sulfate, dimethyl sulfate, benzyl chloride, dodecylbenzyl chloride and methyl chloride;
  • composition of claim 1 wherein the amount of water is about 74 percent.
  • 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.
  • 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.
  • a softened textile material which has been treated with the softening composition of claim 1.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US37875A 1967-04-03 1970-05-15 Aqueous textile softening composition Expired - Lifetime US3664952A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US62767267A 1967-04-03 1967-04-03
US3787570A 1970-05-15 1970-05-15

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3973065A (en) * 1973-10-04 1976-08-03 Microfibres, Inc. Synthetic suede
US4085245A (en) * 1976-04-15 1978-04-18 Xerox Corporation Transparencies for color xerographic copies
US4238373A (en) * 1978-03-06 1980-12-09 The Procter & Gamble Company Process for making detergent compositions containing nitrogenous cationic surfactants
US4446032A (en) * 1981-08-20 1984-05-01 International Flavors & Fragrances Inc. Liquid or solid fabric softener composition comprising microencapsulated fragrance suspension and process for preparing same
US4464271A (en) * 1981-08-20 1984-08-07 International Flavors & Fragrances Inc. Liquid or solid fabric softener composition comprising microencapsulated fragrance suspension and process for preparing same
CN103437170A (zh) * 2013-09-14 2013-12-11 邢柯君 一种纺织面料的多效柔滑剂及其制备方法和用途

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2160458A (en) * 1935-10-31 1939-05-30 Du Pont Artificial thread dressing composition
US2205042A (en) * 1937-10-26 1940-06-18 Du Pont Softening of textile materials and compositions therefor
US2213673A (en) * 1937-10-25 1940-09-03 Ninol Inc Treatment of textiles
US2862009A (en) * 1952-12-12 1958-11-25 Ciba Ltd New water soluble quaternary ammonium salts
US3091552A (en) * 1960-05-06 1963-05-28 Courtaulds Ltd Process for increasing the resistance of polyacrylonitrile fibers to discoloration
US3154489A (en) * 1960-07-18 1964-10-27 Armour & Co Surface active compositions

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2160458A (en) * 1935-10-31 1939-05-30 Du Pont Artificial thread dressing composition
US2213673A (en) * 1937-10-25 1940-09-03 Ninol Inc Treatment of textiles
US2205042A (en) * 1937-10-26 1940-06-18 Du Pont Softening of textile materials and compositions therefor
US2862009A (en) * 1952-12-12 1958-11-25 Ciba Ltd New water soluble quaternary ammonium salts
US3091552A (en) * 1960-05-06 1963-05-28 Courtaulds Ltd Process for increasing the resistance of polyacrylonitrile fibers to discoloration
US3154489A (en) * 1960-07-18 1964-10-27 Armour & Co Surface active compositions

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3973065A (en) * 1973-10-04 1976-08-03 Microfibres, Inc. Synthetic suede
US4085245A (en) * 1976-04-15 1978-04-18 Xerox Corporation Transparencies for color xerographic copies
US4238373A (en) * 1978-03-06 1980-12-09 The Procter & Gamble Company Process for making detergent compositions containing nitrogenous cationic surfactants
US4446032A (en) * 1981-08-20 1984-05-01 International Flavors & Fragrances Inc. Liquid or solid fabric softener composition comprising microencapsulated fragrance suspension and process for preparing same
US4464271A (en) * 1981-08-20 1984-08-07 International Flavors & Fragrances Inc. Liquid or solid fabric softener composition comprising microencapsulated fragrance suspension and process for preparing same
CN103437170A (zh) * 2013-09-14 2013-12-11 邢柯君 一种纺织面料的多效柔滑剂及其制备方法和用途
CN103437170B (zh) * 2013-09-14 2015-10-28 邢柯君 一种纺织面料的多效柔滑剂及其制备方法和用途

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NL6803446A (it) 1968-10-04

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