EP0293955B1 - Composés d'isopropylester ammonium quaternaires comme compositions de traitement pour les fibres et les matières textiles - Google Patents

Composés d'isopropylester ammonium quaternaires comme compositions de traitement pour les fibres et les matières textiles Download PDF

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Publication number
EP0293955B1
EP0293955B1 EP88200819A EP88200819A EP0293955B1 EP 0293955 B1 EP0293955 B1 EP 0293955B1 EP 88200819 A EP88200819 A EP 88200819A EP 88200819 A EP88200819 A EP 88200819A EP 0293955 B1 EP0293955 B1 EP 0293955B1
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Prior art keywords
softener
composition according
fabric
compositions
softener compound
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German (de)
English (en)
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EP0293955A3 (en
EP0293955A2 (fr
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Darlene Rose Walley
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Procter and Gamble Co
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Procter and Gamble Co
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid

Definitions

  • the present invention relates to textile treatment compositions.
  • it relates to textile treatment compositions for use in the rinse cycle of a textile laundering operation to provide fabric softening/static control benefits, the compositions being characterized by excellent storage stability and viscosity characteristics and biodegradability.
  • the compositions herein can also be used to treat fabrics in hot air clothes dryers, and in hair conditioner compositions.
  • rinse-added fabric softening compositions contain, as the active softening component, substantially water-insoluble cationic materials having two long alkyl chains. Typical of such materials are di-stearyl di-methyl ammonium chloride and imidazolinium compounds substituted with two stearyl groups.
  • Cationic softener materials are normally supplied by the manufacturer in the form of a slurry containing about 70%-80% of active material in an organic liquid such as isopropanol, sometimes containing a minor amount of water (up to about 10%).
  • Retail fabric softening compositions are then prepared by dispersion of the softener slurry in warm water under carefully controlled conditions.
  • the physical form and dispersibility constraints of these industrial concentrates are such as to preclude their direct use by the domestic consumer; indeed, they can pose severe processing problems even for the industrial supplier of retail fabric softening compositions.
  • European Patent 0,018,039, Clint, et al, March 7, 1984, relates to hydrocarbons plus soluble cationic or nonionic surfactants in softener concentrates to improve viscosity and stability characteristics.
  • U.S. Patent 4,454,049 MacGilp, et al, June 12, 1984 discloses liquid textile treatment compositions in the form of isotropic solutions comprising water-insoluble di-C16-C24 optionally hydroxy-substituted alkyl, alkaryl or alkenyl cationic fabric softeners, at least about 70% of the fabric softener consisting of one or more components together having a melting completion temperature of less than about 20°C, a water-insoluble nonionic extender, especially C10-C40 hydrocarbons or esters of mono- or polyhydric alcohols with C8-C24 fatty acids, and a water-miscible organic solvent.
  • the concentrates have improved formulation stability and dispersibility, combined with excellent fabric softening characteristics.
  • U.S. Patent 4,476,031, Ooms, Oct. 9, 1984 teaches ethoxylated amines, or protonated derivatives thereof, in combination with ammonium, imadazolinium, and the like materials.
  • alkoxylated amines, as a class, in softener compositions is known (see, for example, German Patent Applications Nos. 2829022 and 1,619,043 and U.S. Patent Nos. 4,076,632 and 4,157,307).
  • fabric softener concentrates which contain a mixture of a fatty quaternary ammonium salt having at least one C8-C30 alkyl substituent and an oil or substantially water-insoluble compound having oily/fatty properties.
  • the concentrates are said to be easily dispersed/emulsified in cold water to form fabric softening compositions.
  • Concentrated dispersions of softener material can be prepared as described in European Patent Application No. 406 and U.K. Patent No. 1,601,360 by incorporating certain nonionic adjunct softening materials therein.
  • each R substituent is a short-chain (C1-C6, preferably C1-C3) alkyl or hydroxyalkyl group, e.g., methyl (most preferred), ethyl, propyl, hydroxyethyl, and the like, or mixtures thereof; each R' is a long-chain hydrocarbyl substituent, e.g., C13-C17, preferably C15 alkyl, or mixtures thereof; and R'' is a short-chain (C1-C4) hydrocarbyl substituent, especially methyl.
  • the counterion X ⁇ is not critical herein, and can be, for example, halide, methylsulfate, and the like. It will be understood that substituents R, R' and R'' may optionally be substituted with various groups such as alkoxyl, hydroxyl, or can be branched, but such materials are not preferred herein.
  • the preferred compounds can be considered to be quaternized di-esters of di-isopropanol amines.
  • ester moieties lend biodegradability to these compounds, whereas the chain branching of the isopropyl moiety provides sufficient hydrolytic stability that the compounds can be stably formulated as liquid compositions, under the conditions disclosed hereinafter.
  • the desirable viscosity characteristics of the compounds which allows them to be formulated as concentrates are entirely unexpected. Since the compounds are cationic, they provide not only fiber and fabric softness, but also anti-static benefits.
  • the present invention encompasses liquid fabric softening and antistatic compositions, comprising: a liquid carrier; and at least about 1% by weight of a fabric softener compound of the above-disclosed formula dissolved or, preferably, dispersed in said carrier.
  • Such liquid compositions are most preferably formulated at a pH of from about 1.5 to about 5.0 to provide good storage stability.
  • Such compositions will typically comprise from about 3% to about 15% by weight of the softener compound.
  • the liquid compositions herein have the softener compound present as particles dispersed in the carrier.
  • the particles are sub-micrometer size, generally having average diameters in the range of about 0.15-0.45 micrometers.
  • Such particle dispersions can optionally be stabilized with emulsifiers.
  • liquid compositions herein are substantially free (generally, less than 1%) of free (i.e., unprotonated) amines, since free amines can catalyze decomposition of the softener compounds, on storage. However, if minor amounts of amines are present, they should be protonated with acid during formulation of the compositions. Strong acids, such as H3PO4 and HCl, can be used for this purpose.
  • the low viscosities exhibited by dispersions of particles of the compounds herein allows them to be formulated as water-dilutable fabric softener "high concentrates" which contain from about 16% to about 25% by weight of the fabric softener compound.
  • high concentrates are conveniently packaged in pouches, which can be diluted with water to "single-strength" softeners (typically, 3-5% concentration of softener active) by the user.
  • the compounds herein can also be formulated as solids, for example, in combination with particulate carriers as particulate fabric softening and antistatic compositions.
  • particulate carriers as particulate fabric softening and antistatic compositions.
  • the pH and presence or absence of amines are, of course, not as critical as with the liquid compositions, since stability to hydrolysis on storage is not so problematic.
  • solid compositions herein have the compounds releasably affixed to sheet materials to provide fabric softening and antistatic compositions in sheet form which can be used in hot air clothes dryers.
  • the invention also encompasses a method of softening fibers (including hair) or fabrics, or imparting an antistatic finish thereto, comprising contacting said fibers or fabrics with a compound of the above-disclosed type.
  • the compounds used as the active softener and antistatic ingredient in the practice of this invention are prepared using standard reaction chemistry.
  • an amine of the formula RN(CH2CHR''OH)2 is esterified at both hydroxyl groups with an acid chloride of the formula R'C(O)Cl, then quaternized with an alkyl halide, RX, to yield the desired reaction product (wherein R, R' and R'' are as defined in the above structural formula).
  • RX alkyl halide
  • stable liquid compositions herein are formulated at a pH in the range of about 1.5 to about 5.0, preferably about pH 3 ⁇ 0.5.
  • the pH can be adjusted with standard acids, e.g., HCl, HBr, and the like; H3PO4 is preferred.
  • liquid compositions herein should be substantially free (1%, or less, preferably 0.3%) of amines. While many fully-formulated fabric softener compositions comprise mixtures of various softener compounds, the amine softeners sometimes used in such art-disclosed compositions are preferably not used in the liquid compositions of this invention, since they can catalyze hydrolysis and thereby reduce storage stability. However, it should be appreciated that the liquid and solid compositions herein can optionally contain non-amine softener and antistatic materials, e.g., standard softener "quats” such as ditallow dimethyl ammonium chloride (“DTDMAC”), C14-C18 imidazoliniums, etc., as auxiliary softener/antistat ingredients. Such optional ingredients can typically comprise 1%-10% of the present compositions.
  • non-amine softener and antistatic materials e.g., standard softener "quats” such as ditallow dimethyl ammonium chloride (“DTDMAC”), C14-C18 imidazoliniums
  • the liquid compositions herein comprise a liquid carrier, which is typically water or a mixture of water and an alcohol such as ethanol or iso-propanol (typically 0.5-2.0%alcohol).
  • a liquid carrier typically water or a mixture of water and an alcohol such as ethanol or iso-propanol (typically 0.5-2.0%alcohol).
  • the softener compounds used in this invention are insoluble in such water-based carriers and, thus, are present as a dispersion of fine particles therein. These particles are, as noted above, sub-micrometer in size and are conveniently prepared by high-shear mixing which disperses the compounds as fine particles. Preferred particles have average diameters in the range of from 0.15 - 0.45 micrometers Preparation of a preferred dispersion is disclosed in detail in Example II, hereinafter. Again, since the compounds are hydrolytically labile, care should be taken to avoid the presence of base and to keep the processing temperatures in the range of about 65 to about 85°C, preferably 65-75°C.
  • the particulate dispersions of the foregoing type can optionally be stabilized against settling by means of standard, nor-base emulsifiers, especially nonionics such as the C14 ⁇ 18 ethoxylates (EO8 ⁇ 15), typically used at concentrations of 0.1-2%, according to known practice in the formulation of liquid DTDMAC fabric softener dispersions.
  • standard, nor-base emulsifiers especially nonionics such as the C14 ⁇ 18 ethoxylates (EO8 ⁇ 15), typically used at concentrations of 0.1-2%, according to known practice in the formulation of liquid DTDMAC fabric softener dispersions.
  • fabrics or fibers are contacted with from about 3.0 g to about 9.0 g (per 3.5 kg of fiber or fabric being treated) of the compounds herein in an aqueous bath, or in a hot air clothes dryer.
  • the amount used is at the discretion of the user, depending on fiber or fabric type, degree of softness desired, and the like.
  • about 120 mls. of a 5% dispersion are used in a 25 l laundry rinse bath to soften and provide antistatic benefits to a 3.5 kg load of mixed fabrics.
  • the reaction mixture is cooled to room temperature and diluted with chloroform (1500 mL).
  • the chloroform solution of product is placed in a separatory funnel (4 L) and washed with sat. NaCl, dil. Ca(OH)2, 50% K2CO3, (3 times)*, and, finally, sat. NaCl.
  • the organic layer is collected and dried over MgSO4 and filtered. Solvents are removed via rotary evaporation. Final drying is done under high vacuum (33Pa or 0.25mm Hg). *Note: 50% K2CO3 layer will be below chloroform layer.
  • the nonhydrolytic preparation of the composition of Example II is carried out as follows.
  • the softener compound and the isopropyl alcohol are mixed and warmed (80 to 85°C) to form a fluidized "melt".
  • the melt is then poured into the water (65 to 75°C) with high shear mixing (7000 rpm; 20-25 minutes) to submicronize the softener particles.
  • the dye and minors are added, and the pH is adjusted with H3PO4.
  • the resulting dispersion has a viscosity of about (40 centipoise) 4x10 ⁇ 2 Pa.S ⁇ 1 and is used in standard fashion as a through-the-rinse fabric softener. All liquid compositions herein are prepared in substantially the same manner.
  • dispersions of the softener of Example I in water-isopropyl alcohol (90:10) at 8% (50 cps) 5x10 ⁇ 2 Pa.S ⁇ 1 and 15% (80 cps) (8x10 ⁇ 2 Pa.S ⁇ 1) are prepared.
  • the present compositions can be supplemented by all manner of optional components conventionally used in textile treatment compositions, for example, colorants, perfumes, preservatives, optical brighteners, opacifiers, viscosity modifiers, fabric conditioning agents, surfactants, stabilizers such as guar gum and polyethylene glycol, antishrinkage agents, antiwrinkle agents, fabric crisping agents, spotting agents, soil-release agents, germicides, fungicides, antioxidants such as butylated hydroxy toluene, anticorrosion agents, and the like.
  • optional components conventionally used in textile treatment compositions for example, colorants, perfumes, preservatives, optical brighteners, opacifiers, viscosity modifiers, fabric conditioning agents, surfactants, stabilizers such as guar gum and polyethylene glycol, antishrinkage agents, antiwrinkle agents, fabric crisping agents, spotting agents, soil-release agents, germicides, fungicides, antioxidants such as butylated
  • materials such as DTDMAC, the C16-C18 dialkylimidazoliniums, polydimethylsiloxanes, glycerol monostearate, and, as noted above, emulsifiers, especially ethoxylated nonionics, can optionally be used in the present compositions.
  • amines such as TAMET (C18H37N[CH2CH2OH]2) can be present in relatively small amounts (typically 0.3-0.5%) if in the protonated form.
  • Solid carrier materials can be used in place of liquids.
  • the softener compounds can be adsorbed on particulate solids such as potassium sulfate, micronized silica, and the like, and added to a laundry rinse bath.
  • the softeners can be releasably padded onto a sheet (e.g., paper toweling, nonwoven fabric, or the like) and tumbled with damp fabrics in a hot-air clothes dryer, in the manner of the BOUNCE brand dryer-added product known in commercial practice.
  • a sheet e.g., paper toweling, nonwoven fabric, or the like
  • tumbled with damp fabrics in a hot-air clothes dryer, in the manner of the BOUNCE brand dryer-added product known in commercial practice.
  • such solid-form compositions will comprise 80-99% carrier and 1-20% softener.
  • a dryer-additive sheet is prepared by warming 5 g. of the softener compound of Example I in 6 g. isopropanol to prepare a melt in the manner of Example II.
  • the melt is evenly spread onto and into an ordinary, disposable paper hand towel (20 cm x 20 cm) and allowed to dry.
  • the impregnated towel is commingled and tumbled with wet fabrics (5 kg load of fabrics, dry weight basis) in a standard hot air clothes dryer until the fabrics are dry, to provide a soft, antistatic finish.
  • a liquid fabric softener as a particulate, sub-micron dispersion is prepared according to Example II, and has the following composition: Ingredient Percent (wt.) DTDMAC 2.0 Softener compound* 4.0 C11 ⁇ 15 alcohol EO10 (avg) 0.5 Isopropyl alcohol 7.5 Water Balance H3PO4 To pH 1.5-5.0 *Per Example I
  • a particulate softener comprises the following. Ingredient Percent (wt.) Micronized silica 90.0 Softener compound* 7.0 Na2SO4 2.0 C11 ⁇ 15 alcohol (EO)15 1.0 *(C2H5)2 ⁇ N[CH2CH(CH3)OC(O)C17H35]2Br ⁇
  • Example V The composition of Example V is prepared by co-melting the softener compound, ethoxylated alcohol, and an equal weight of ethanol, with gentle warming, then spraying the melt uniformly onto the particulate silica/sodium sulfate.
  • a high concentrate liquid fabric softener comprises the following. Ingredient Percent (wt.) Softener compound* 20 Isopropyl alcohol 2.0 Water Balance H3PO4 To pH 1.5-5.0 *Per Example I
  • Example, VI is prepared in the manner of Example II, as sub-micrometer particles suspended in liquid.
  • the composition is packaged in a simple plastic pouch, which is opened and poured into 4X its volume of water prior to use to prepare a "single strength" softener composition, thereby saving on packaging and shipping costs and storage space.
  • the single strength composition prepared from the concentrate of Example VI can be applied to human or animal hair, typically after shampooing, to provide a soft, lubricious feel.
  • di-isopropanol amine feedstocks used herein may contain varying amounts of mono-isopropanol amines and tri-isopropanol amines. Accordingly, the commercial-grade ester reaction products will comprise, in addition to the di-ester softeners, various amounts of mono- and tri-esters. Moreover, it may be more economical, on a commercial scale, to prepare the esters herein using acids and appropriate catalysts, rather than acid chlorides. Importantly, the preferred compounds herein function well at temperatures lower than many art-disclosed fabric softeners, making them more useful in hot air clothes dryers, as well as performing well when fabrics are line-dried.

Claims (15)

  1. Composition liquide adoucissante et antistatique pour textiles, comprenant :
    a) un véhicule liquide; et
    b) au moins environ 1% en poids d'un composé adoucissant de formule
    Figure imgb0011
     dons laquelle chaque R est un groupe alkyle ou hydroxyalkyle en C₁-C₆, ou des mélanges de ceux-ci; chaque R' est un groupe hydrocarboné à chaîne longue, ou des mélanges de ceux-ci; R'' est un groupe hydrocarboné en C₁-C₄; et X est un contre-ion, dans laquelle ledit composé adoucissant est présent en particules de taille inférieure au micromètre, dispersées dans le véhicule.
  2. Composition selon la revendication 1, dans laquelle chaque R est un groupe alkyle en C₁-C₃ et R'' est un groupe méthyle.
  3. Composition selon les revendications précédentes, dans laquelle chaque R' est un groupe alkyle en C₁₃-C₁₇.
  4. Composition selon les revendications précédentes, dans laquelle chaque groupe R est un groupe méthyle.
  5. Composition selon les revendications précédentes, qui est formulée à un pH d'environ 1,5 à environ 5,0.
  6. Composition selon les revendications précédentes, qui contient d'environ 3% à environ 15% en poids du composé adoucissant. .
  7. Composition selon les revendications précédentes, dans laquelle les particules ont un diamètre moyen dans la gamme de 0,2-0,45 µm.
  8. Composition selon les revendications précédentes, qui contient en outre un émulsifiant. . !
  9. Composition selon les revendications précédentes, qui ne contient pratiquement pas d'amines non protonées.
  10. Composition selon les revendications précédentes, dans laquelle le composé adoucissant est
    Figure imgb0012
  11. Haut concentré d'adoucissant pour textiles diluable à l'eau selon les revendications précédentes, qui contient d'environ 16% à environ 25% en poids du composé adoucissant pour textiles.
  12. Composition selon les revendications précédentes, qui est conditionnée dans un sachet.
  13. Composition adoucissante et antistatique pour le linge sous forme solide, comprenant :
    a) un véhicule solide; et
    b) au moins environ 1% en poids d'un composé adoucissant de formule
    Figure imgb0013
     dans laquelle chaque R est un groupe alkyle ou hydroxyalkyle en C₁-C₆, ou des mélanges de ceux-ci; chaque R' est un groupe hydrocarboné à chaîne longue, ou des mélanges de ceux-ci; R'' est un groupe hydrocarboné en C₁-C₄; et X est un contre-ion, ledit composé adoucissant étant fixé audit véhicule de façon libérable.
  14. Composition selon la revendication 13, dans laquelle le véhicule solide est un substrat en feuille.
  15. Procédé pour adoucir ou pour conférer à des fibres ou à des matières textiles un fini antistatique, par mise en contact desdites fibres ou desdites matières textiles avec une composition selon l'une quelconque des revendications précédentes.
EP88200819A 1987-05-01 1988-04-27 Composés d'isopropylester ammonium quaternaires comme compositions de traitement pour les fibres et les matières textiles Expired - Lifetime EP0293955B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT88200819T ATE84566T1 (de) 1987-05-01 1988-04-27 Quaternaere isopropylesterammonium-verbindungen als faser- und gewebebehandlungsmittel.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US4597687A 1987-05-01 1987-05-01
US45976 1987-05-01

Publications (3)

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EP0293955A2 EP0293955A2 (fr) 1988-12-07
EP0293955A3 EP0293955A3 (en) 1989-07-05
EP0293955B1 true EP0293955B1 (fr) 1993-01-13

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EP (1) EP0293955B1 (fr)
AT (1) ATE84566T1 (fr)
DE (1) DE3877422T2 (fr)
GB (1) GB8810310D0 (fr)

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PL2847307T3 (pl) 2012-05-07 2016-10-31 Aktywna kompozycja do zmiękczania tkanin i sposób jej wytwarzania
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BR102014025172B1 (pt) 2013-11-05 2020-03-03 Evonik Degussa Gmbh Método para fabricação de um éster de ácido graxo de metisulfato de tris-(2-hidroxietil)-metilamônio, e composição ativa de amaciante de roupa
EP2997959B1 (fr) 2014-09-22 2019-12-25 Evonik Operations GmbH Formulation contenant des esterquats a base d'isopropanolamine et de tetrahydroxypropylethylenediamine
UA119182C2 (uk) 2014-10-08 2019-05-10 Евонік Дегусса Гмбх Активна композиція для пом'якшувача тканини

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Also Published As

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EP0293955A3 (en) 1989-07-05
DE3877422D1 (de) 1993-02-25
EP0293955A2 (fr) 1988-12-07
DE3877422T2 (de) 1993-05-13
ATE84566T1 (de) 1993-01-15
GB8810310D0 (en) 1988-06-02

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