EP0510879A2 - Flüssiger Weichmacher - Google Patents

Flüssiger Weichmacher Download PDF

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Publication number
EP0510879A2
EP0510879A2 EP92303461A EP92303461A EP0510879A2 EP 0510879 A2 EP0510879 A2 EP 0510879A2 EP 92303461 A EP92303461 A EP 92303461A EP 92303461 A EP92303461 A EP 92303461A EP 0510879 A2 EP0510879 A2 EP 0510879A2
Authority
EP
European Patent Office
Prior art keywords
group
carbon atoms
chain
branched
saturated
Prior art date
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.)
Withdrawn
Application number
EP92303461A
Other languages
English (en)
French (fr)
Other versions
EP0510879A3 (en
Inventor
Toru Hayase
Kazutaka Shiratsuchi
Junichi Inokoshi
Masaaki Yamamura
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from JP3097207A external-priority patent/JP3021749B2/ja
Priority claimed from JP3097206A external-priority patent/JP3021748B2/ja
Application filed by Kao Corp filed Critical Kao Corp
Publication of EP0510879A2 publication Critical patent/EP0510879A2/de
Publication of EP0510879A3 publication Critical patent/EP0510879A3/en
Withdrawn legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/645Mixtures of compounds all of which are cationic
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/001Softening compositions
    • C11D3/0015Softening compositions liquid

Definitions

  • the present invention relates to a softener.
  • the present invention relates to a liquid softener for domestic use capable of imparting excellent softeness and spring or resiliency (fluffiness) to various fibers and textiles.
  • the quaternary ammonium salt has a remarkable softening effect on cotton, its effect on synthetic fibers such as acrylic fibers, polyesterfibers and polyamide fibers is inadequate. Therefore the above-described domestic softeners tend to be used on such fibers at a high concentration, and the resiliency and feel of the treated clothes are thus often impaired.
  • substances other than the softening component such as polyoxyethylene nonionic surfactant, an electrolyte and a solvent are required to stabilize the softeners, although their effect is still insufficient.
  • Softeners comprising the aforementioned quaternary ammonium salt as the main ingredient are available on the market usually in the form of a 4 to 20 wt.% dispersion of the quaternary ammonium salt.
  • the quaternary ammonium salt having strong hydrophobic properties, is not easily dispersible in water and, as a result, it tends to become deposited unevenly on the clothing being treated.
  • the commercially available softeners contain various additives in addition to the quaternary ammonium salt in order to improve their disperisibility in water, their effect is still insufficient.
  • Liquid softeners containing an amine as the softening ingredient are already known.
  • GB-1,514,276 discloses a composition for softening fibers which comprised a long-chain alkylamine such as a methyl di(hardened tallow alkyl)amine.
  • US-4,446,034 discloses a finishing agent for fibrous materials to impart smoothness and excellent touch to the fibers which comprises an acylated alkanolamine, a water-soluble quaternary ammonium salt and a fatty acid ester.
  • US-4,776,965 discloses a softener having a high disperisibility which comprises a quaternary ammonium compound, a higher fatty acid and a hydroxylated lower alkyl polyamine polyglycol ether.
  • US-4,724,089 discloses a stable aqueous dispersion for treating textiles which comprises a di(higher alkyl) cyclic amine and a Bronsted acid.
  • US-4,913,828 discloses a softening composition comprising a di(long chain alkyl)amine/anoinic surfactant ion pair complex, a non-silicone wax and a liquid carrier.
  • EP-332,270 discloses a conditioning composition for cloth which comprises an amine such as a condensate of a hydroxylated lower alkyl alkylene diamine with a higherfatty acid and an amphoteric conditioning agent for cloth.
  • US-4,869,836 discloses a softener comprising a di(long chain alkyl) amine/polyfunctional carboxylic acid complex and a conditioning composition for imparting antistatic properties to cloth.
  • US-4,045,361 discloses a cloth conditioning composition which comprises an antistatic agent comprising a mono- or di(long chain alkyl)alkylenediamine and a quaternary ammonium softening agent.
  • an antistatic agent comprising a mono- or di(long chain alkyl)alkylenediamine and a quaternary ammonium softening agent.
  • the present invention provides a liquid softener comprising or essentially consisting of (a) an amine having one or two ester group(s) and at least two straight-chain or branched, saturated or unsaturated hydrocarbon groups having 11 to 23 carbon atoms in the molecule and neutralized with an inorganic acid or an organic acid, and 5 to 100% by weight, based on the component (a), of (b) an alkylamine polyester compound selected from compounds represented by the following general formulae (I) to (III) and/or 1 to 150% by weight, based on the component (a), of (c) a compound having a long-chain hydrocarbon group, a nitrogen atom and at least one member selected from an ester group, an amide group and an imidazoline skeleton in the molecule: wherein R 3 represents a straight-chain or branched, saturated or unsaturated hydrocarbon group having 8 to 24 carbon atoms, p 1 + P 2 + P 3 + p 4 is an integer from 0 to 60 and q + + q 2
  • Typical examples of component (a) to be used in the present invention include compounds produced by neutralizing an ester amine with an inorganic acid such as hydrochloric acid and sulfuric acid or an organic acid such as acetic acid, glycolic acid, lactic acid, citric acid, maleic acid, fumaric acid and toluenesulfonic acid, the ester amine being produced by reacting an alkanolamine such as triethanolamine, tripropanolamine, N-methyldiethanolamine, N-methylpropanolamine and an N-(long chain alkyl)diethanolamine with a fatty acid having 12 to 24 carbon atoms or the methyl ester thereof.
  • the fatty acids to be used in this reaction are usually those derived from natural oils and fats such as coconut oil, palm oil, tallow, rapeseed oil and fish oil, and chemically synthesized fatty acids are also usable.
  • ester amine compounds which are precursors of component (a) are preferably those having one or two ester groups, particularly preferably those having one or two ester group(s) in the following form: and/or wherein R 1 and R Z each represent a straight-chain or branched, saturated or unsaturated hydrocarbon group having 11 to 23 carbon atoms, and two straight-chain or branched, saturated or unsaturated hydrocarbon groups having 11 to 23 carbon atoms.
  • the ester amine compound as a precursor of component (a) includes those of the following general formulae (IV) to (VII) as particularly preferably examples thereof.
  • ester amine compounds those of the above formula wherein R 1 and R 2 each represent an alkyl group or an alkenyl group having at least 14 carbon atoms are desirable, and those of the above formula wherein R 1 and R 2 each represent an alkyl group or an alkenyl group having at least 15 carbon atoms are still more desirable.
  • the component (a) may be used either singly or in the form of a mixture of two or more of them.
  • the amount of the component (a) is preferably 1 to 30% by weight, more preferably 4 to 30% by weight and particularly preferably 10 to 25% by weight, based on the entire liquid softener of the present invention.
  • component (a) having an ester group in the molecule to be used in the present invention it has a high biodegradability and is usable as an ingredient which is harmless to the physical environment.
  • the alkylamine polyether compound to be used as component (b) of the liquid softener of the present invention is selected from the compounds represented by the aforementioned general formulae (I) to (III).
  • the alkylamine polyether compounds can be produced by the addition reaction of a corresponding amine with propylene oxide and/or ethylene oxide.
  • propylene oxide is desirably added at first from the viewpoint of ease of synthesis.
  • an alkylamine polyether compound which p 1 + p 2 + p 3 + P4 in the aforementioned general formulae (I) to (III) is an integer from O to 20 and/or q 1 + q 2 + q 3 + q 4 in the aforementioned general formulae (I) to (III) is an integer from 0 to 40 is preferable.
  • the component (b) may be used either singly or in the form of a mixture of two or more of them.
  • the amount of the component (b) is 5 to 100% by weight, preferably 6 to 70% by weight and more preferably 20 to 35% by weight, based on the component (a) (from the economic point of view, 20 to 35% by weight is particularly preferred).
  • the compound to be used as the component (c) in the present invention is a compound having a long-chain hydrocarbon group, a nitrogen atom and at least one member selected from an ester group, an amide group and an imidazoline skeleton in the molecule.
  • the compounds to be used as the component (c) in the present invention can be easily synthesized from alcohols or amines.
  • component (c) examples include those derived from N-methyldiethanolamine, imidazoline derivatives and aminoethylethanolamine derivatives. Particularly preferred are compounds of the following general formulae (VIII) to (XII):
  • Component (c) may be used either singly or in the form of a mixture of two or more of them.
  • the amount of component (c) is 1 to 150% by weight, preferably 5 to 100% by weight and more preferably 10 to 50% by weight, based on the component (a) (from the viewpoint of storability of the liquid softener, 5 to 50% by weight is particularly preferred).
  • the liquid softener of the present invention can be prepared, for example, by slowly adding a molten amine as component (a) or a solution of the amine having a high concentration to an aqueous solution containing a neutralizing agent, i.e. an inorganic acid or an organic acid, and component (b), component (c), a silicone compound, a solvent, etc., with stirring or shear mixing, and then adding an inorganic electroyte, a colorant and a perfume.
  • the inorganic electroyte may be previously added to the aqueous solution containing a neutralizing agent etc., or the silicone compound may be added after adding component (a).
  • the method for the preparation of the liquid softener is not limited thereto but it can be prepared by other methods, also e.g. by adding a previously produced neutralized product (component (a)) or by the post-addition of the neutralized product.
  • the feel of the clothes softened with the softener of the present invention can be further improved without impairing their water absorption by further incorporating into the softener a silicone compound such as dimethylpolysiloxane itself or dimethyl-polysiloxane partially modified with an amino group or a polyoxyalkylene group, particularly preferably dimethylpolysiloxane partially modified with a polyoxyalkylene group.
  • a silicone compound such as dimethylpolysiloxane itself or dimethyl-polysiloxane partially modified with an amino group or a polyoxyalkylene group, particularly preferably dimethylpolysiloxane partially modified with a polyoxyalkylene group.
  • the amount of the silicone compound to be incorporated is preferably 0.3 to 5% by weight based on compnent (a).
  • the softening effect of the softener of the present invention is equivalent to that of a commonly- used softener comprising hardened tallow alkyldimethylammonium chloride as the main ingredient, it has been suprisingly found that the softener of the present invention imparts to the clothes a high resiliency (fluffiness) in addition to softeness.
  • the softener of the present invention is produced in the form of an aqueous liquid softener, it is desirable for it to contain 0.05 to 0.4% by weight, based on the entire liquid softener, of an inorganic electrolyte such as sodium chloride, calcium chloride and magnesium chloride in order to regulate the viscosity.
  • an inorganic electrolyte such as sodium chloride, calcium chloride and magnesium chloride
  • the liquid softener of the present invention has good storage stability for a long period of time, its stability under severe conditions can be further improved by the incorporation of a nonionic surfactant such as a polyoxyethylene(5 to 50 mol)alkyl(C 12 to C 24 )ether and a polyoxyethylene (5 to 50 mol)alkenyl(C 12 to C 24 )ether, a solvent such as ethanol, propylene glycol and ethylene glycol, or urea.
  • a known softener base such as an ester, a nonionic compound, a cationic compound, a long-chain alcohol and a long-chain fatty acid may be contained in the liquid softener of the present Invention.
  • a pigment or a dye can be used for Improving the appearance of the product and a fluorescent brightener can be used for whitening the finished textile, while a fragrance can be used for improving the appeal during the use of the product and after the finish
  • the softener of the present invention is capable of imparting sufficient softness and antistatic properties to various fibers and has an excellent biodegradability.
  • the cloths treated as described above were air-dried indoors and then left to stand in an air-conditioned room at 25°C and 65% RH for 24 hours to evaluate the softness and resiliency of the cloths
  • the liquid softeners of the present invention for clothes were substantially unchanged with time and were excellent.
  • the softening effect of the softeners of the present invention were slightly better than or equivalent to that of the control, and the resilient effect of the cloth using the softeners of the present invention was better than or slightly better than that of the control.
  • the liquid softeners of the present invention for clothes were substantially unchanged with time and were excellent.
  • the softening effect of the softeners of the present invention were slightly better than or equivalent to that of the control, and the resilient effect in the cloth using the softeners of the present invention was better than or slightly better than that of the control.
  • the liquid softener having the fllowing formulation was evaluated as described in Example 1.
  • This liquid softener gave excellent softness and resilience to a cloth.
  • the storage stability and the dispersibility in water for rinse were also excellent.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP19920303461 1991-04-26 1992-04-16 Liquid softener Withdrawn EP0510879A3 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP3097207A JP3021749B2 (ja) 1991-04-26 1991-04-26 液体柔軟仕上剤
JP97207/91 1991-04-26
JP3097206A JP3021748B2 (ja) 1991-04-26 1991-04-26 液体柔軟仕上剤
JP97206/91 1991-04-26

Publications (2)

Publication Number Publication Date
EP0510879A2 true EP0510879A2 (de) 1992-10-28
EP0510879A3 EP0510879A3 (en) 1993-03-17

Family

ID=26438393

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19920303461 Withdrawn EP0510879A3 (en) 1991-04-26 1992-04-16 Liquid softener

Country Status (2)

Country Link
EP (1) EP0510879A3 (de)
MX (1) MX9201827A (de)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2735384A1 (fr) * 1995-06-14 1996-12-20 Rhone Poulenc Chimie Composition tensioactive a base d'amidoamines polyacoxylees
US5670476A (en) * 1991-04-30 1997-09-23 The Procter & Gamble Company Fabric softening compositions containing mixtures of substituted imidazoline fabric softener materials and highly ethoxylated curd dispersant
US6180593B1 (en) * 1998-09-30 2001-01-30 Goldschmidt Rewo Gmbh & Co. Kg Fabric softeners with improved color-retaining action
EP1299070A1 (de) * 2000-06-13 2003-04-09 Finetex, Inc. Neue quaternäre ammoniumverbindungen und verfahren zu deren herstellung und verwendung
US8026206B2 (en) 2005-05-18 2011-09-27 Stepan Company Low solids, high viscosity fabric softener compositions and process for making the same
US8597668B2 (en) 2009-02-09 2013-12-03 L'oreal Clear carrier compositions for lipophilic compounds, and method of treating keratinous substrates using such compositions
US8637489B2 (en) 2009-02-09 2014-01-28 L'oreal Clear carrier compositions for lipophilic compounds, and method of treating keratinous substrates using such compositions

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2322963A1 (fr) * 1975-09-04 1977-04-01 Hoechst Ag Assouplissants pour matieres textiles
EP0085933A2 (de) * 1982-02-06 1983-08-17 Hoechst Aktiengesellschaft Konzentrierte Wäscheweichspülmittel
EP0345842A2 (de) * 1988-05-27 1989-12-13 The Procter & Gamble Company Wäscheweichspülerzusammensetzungen, die Mischungen substituierter Imidazolinester und quaternärer Esterammoniumsalze enthalten
EP0375029A2 (de) * 1988-12-21 1990-06-27 The Procter & Gamble Company Verfahren zur Erstellung von substituierten Imidazolinen, geeignet für die Behandlung von Textilien
EP0443313A1 (de) * 1990-01-19 1991-08-28 Kao Corporation Flüssige Textilweichmacherzusammensetzung
EP0472178A1 (de) * 1990-08-22 1992-02-26 Kao Corporation Textilweichmacherzusammensetzung

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2322963A1 (fr) * 1975-09-04 1977-04-01 Hoechst Ag Assouplissants pour matieres textiles
EP0085933A2 (de) * 1982-02-06 1983-08-17 Hoechst Aktiengesellschaft Konzentrierte Wäscheweichspülmittel
EP0345842A2 (de) * 1988-05-27 1989-12-13 The Procter & Gamble Company Wäscheweichspülerzusammensetzungen, die Mischungen substituierter Imidazolinester und quaternärer Esterammoniumsalze enthalten
EP0375029A2 (de) * 1988-12-21 1990-06-27 The Procter & Gamble Company Verfahren zur Erstellung von substituierten Imidazolinen, geeignet für die Behandlung von Textilien
EP0443313A1 (de) * 1990-01-19 1991-08-28 Kao Corporation Flüssige Textilweichmacherzusammensetzung
EP0472178A1 (de) * 1990-08-22 1992-02-26 Kao Corporation Textilweichmacherzusammensetzung

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5670476A (en) * 1991-04-30 1997-09-23 The Procter & Gamble Company Fabric softening compositions containing mixtures of substituted imidazoline fabric softener materials and highly ethoxylated curd dispersant
FR2735384A1 (fr) * 1995-06-14 1996-12-20 Rhone Poulenc Chimie Composition tensioactive a base d'amidoamines polyacoxylees
WO1997000126A1 (fr) * 1995-06-14 1997-01-03 Rhone-Poulenc Chimie Composition tensioactive a base d'amidoamines polyalcoxylees
US6180593B1 (en) * 1998-09-30 2001-01-30 Goldschmidt Rewo Gmbh & Co. Kg Fabric softeners with improved color-retaining action
EP1299070A1 (de) * 2000-06-13 2003-04-09 Finetex, Inc. Neue quaternäre ammoniumverbindungen und verfahren zu deren herstellung und verwendung
EP1299070A4 (de) * 2000-06-13 2004-10-27 Finetex Inc Neue quaternäre ammoniumverbindungen und verfahren zu deren herstellung und verwendung
US8026206B2 (en) 2005-05-18 2011-09-27 Stepan Company Low solids, high viscosity fabric softener compositions and process for making the same
US8597668B2 (en) 2009-02-09 2013-12-03 L'oreal Clear carrier compositions for lipophilic compounds, and method of treating keratinous substrates using such compositions
US8637489B2 (en) 2009-02-09 2014-01-28 L'oreal Clear carrier compositions for lipophilic compounds, and method of treating keratinous substrates using such compositions

Also Published As

Publication number Publication date
MX9201827A (es) 1992-10-01
EP0510879A3 (en) 1993-03-17

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