EP2909294B1 - Textilweichmacherzusammensetzung mit trialkanolamin-basiertem esterquat - Google Patents

Textilweichmacherzusammensetzung mit trialkanolamin-basiertem esterquat Download PDF

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Publication number
EP2909294B1
EP2909294B1 EP13779188.5A EP13779188A EP2909294B1 EP 2909294 B1 EP2909294 B1 EP 2909294B1 EP 13779188 A EP13779188 A EP 13779188A EP 2909294 B1 EP2909294 B1 EP 2909294B1
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EP
European Patent Office
Prior art keywords
trialkanolamine
liquid fabric
fabric softener
softener composition
esterquat
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.)
Active
Application number
EP13779188.5A
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German (de)
English (en)
French (fr)
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EP2909294A1 (de
Inventor
Tatiana Schymitzek
Carine Wattebled
Dietmar SCHRÖTER
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.)
Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Priority to PL13779188T priority Critical patent/PL2909294T3/pl
Publication of EP2909294A1 publication Critical patent/EP2909294A1/de
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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
    • 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
    • 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
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/30—Amines; Substituted amines ; Quaternized amines

Definitions

  • the invention relates to a liquid fabric softening composition with trialkanolamine-based esterquat.
  • Fabric softeners are added to the laundry in the last rinse of the machine wash to prevent the effect of "dry drying” occurring during drying laundry.
  • the dry rigidity is due to the formation of hydrogen bonds between the cellulose fibers.
  • the cationic, softening compounds of the softener penetrate into the fiber or lie on the fiber surface, combine with the negative charges and weaken the interactions. Due to the reduced stiffness of the garment, the force required for ironing is reduced and the wearing comfort is increased.
  • Liquid fabric softeners are divided into two types: "normal” fabric softeners containing from 1 to 5% by weight of softening compounds and "concentrated” fabric softeners containing from 5 to 80% by weight of softening compounds.
  • the acceptance of a fabric softener product by the users is determined not only by the actual performance but also strongly by the viscosity of the product, with medium to high viscosities preferred by the users.
  • viscosities in the range of 10 to 400 mPas and for concentrated fabric softeners in the range of 100 to 600 mPas (each determined with a Brookfield viscometer RV DV II + P, spindle 2 at 20 rpm and 20 ° C).
  • the thickeners used often do not themselves show any softening performance and increase the production costs of the softener. Also, not all thickeners are compatible with the ingredients used in fabric softeners.
  • liquid fabric softening composition containing from 0.5 to 40% by weight, based on the total fabric softening composition, of a softening mixture of trialkanolamine-based esterquat and trialkanolamine-based ester, the liquid fabric softening composition being free of methanol, wherein the ratio of trialkanolamine-based esterquat to trialkanol-based ester is between 2: 1 and 4: 1.
  • liquid fabric softening compositions comprising a mixture of a trialkanolamine-based esterquat and a trialkanolamine-based ester and which are further free of methanol have higher viscosities than liquid fabric softening compositions containing no trialkanol-based ester and small amounts (US Pat. ⁇ 50 ppm) methanol.
  • textiles treated with such a liquid fabric softening composition exhibit increased / improved softening.
  • a particularly strong increase in viscosity can be obtained in liquid fabric softening compositions in which the amount of fabric softening mixture is from 3 to 18% by weight, based on the total liquid fabric softening composition.
  • the invention also relates to the use of a methanol-free, softening mixture of trialkanolamine-based esterquat and trialkanolamine-based ester for increasing the viscosity of a liquid fabric softening composition wherein the ratio of trialkanolamine-based esterquat to trialkanol-based ester is between 2: 1 and 4: 1 amounts to.
  • the invention also relates to the use of a methanol-free, softening mixture of trialkanolamine-based esterquat and trialkanolamine-based ester in a liquid fabric softening composition for increasing the softness of fabrics treated with the liquid fabric softening composition, wherein the ratio of trialkanolamine-based esterquat to trialkanolamine based ester is between 2: 1 and 4: 1.
  • liquid fabric softening compositions according to the invention are described in detail, inter alia, by way of examples.
  • Liquid fabric softening compositions according to the invention comprise a softening mixture which necessarily comprises a trialkanolamine-based esterquat and a trialkanolamine-based ester.
  • trialkanolamine-based ester quats is understood to mean quaternized fatty acid trialkanolamine amine ester salts.
  • the preparation of trialkanolamine-based esterquats is usually carried out in two stages: 1) esterification of trialkanolamine with fatty acids for Trialkanolamine-based ester and 2) quaternization of the resulting esters with dimethyl sulfate or chloromethane.
  • fatty acids RCOOH are used in which RCO is an aliphatic, saturated and / or unsaturated acyl radical having 6 to 22 carbon atoms.
  • Typical examples are caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid, and technical mixtures thereof ,
  • fatty acids having 12 to 18 carbon atoms such as partially cured palm and / or tallow fatty acids having an iodine value in the range of 0.5 to 50 are used. Particularly preferred tallow fatty acids having 12 to 18 carbon
  • the esterification is carried out in the presence of hypophosphorous acid or its salts and optionally reducing agents such as sodium borohydride.
  • the trialkanolamine and the fatty acids are used in a molar ratio of 1: 1.1 to 1: 2.4, preferably the ratio is in the range 1: 1.4 to 1: 1.9.
  • the reaction is carried out at temperatures in the range of 120 to 180 ° C.
  • Suitable trialkanolamines include, for example, triethanolamine, diethanolpropanolamine and tripropanolamine, with triethanolamine being preferred. Accordingly, it is particularly preferred that the trialkanolamine-based ester is a triethanolamine-based ester.
  • the ester is introduced and stirred with the alkylating agent at elevated temperatures (40 to 95 ° C).
  • the reaction can be carried out in alcoholic solution, for example in isopropyl alcohol or ethanol.
  • the alkylation is carried out with dimethyl sulfate.
  • a trialkanolamine-based esterquat particularly preferably obtained by the alkylation is a triethanolamine-based esterquat.
  • trialkanolamine-based esterquats in which the quaternizing agent is used equimolar or in a slight excess to the trialkanolamine-based ester, may contain an increased amount of methanol in the raw material.
  • the methanol can be detected in the raw material as well as in finished formulations, in particular fabric softeners.
  • the content of methanol may be 0.1 to 3 wt .-%.
  • finished formulations depending on the amount of raw material used, 50 to 300 ppm of methanol are contained.
  • trialkanolamine-based esterquat is a compound of the following formula: where R 4 is an aliphatic alk (en) yl radical having 6 to 22 carbon atoms with 0, 1, 2 or 3
  • R 5 is OH or O (CO) R 7
  • R 6 is independently of R 5 OH or O (CO) R 8
  • R 7 and R 8 are each independently an aliphatic alk (en) yl radical with 11 bis 21 carbon atoms with 0, 1, 2 or 3 double bonds.
  • m, n and p may each independently be 1, 2 or 3 and
  • X - may be either halide, methosulfate, methophosphate or phosphate ion as well as mixtures of these anions.
  • R 4 , R 7 and R 8 are derived from tallow fatty acid and X - is a methosulfate ion.
  • Preferred trialkanolamine-based esters are N- (2-hydroxyethyl) -N, N-di (tallowacyloxyethyl) amine, N- (2-hydroxyethyl) -N, N-di (palmacyloxyethyl) amine or N- (2-hydroxyethyl) hydroxyethyl) -N, N-di (stearoyloxyethyl) amine.
  • Preferred trialkanolamine-based ester quats are correspondingly methyl N- (2-hydroxyethyl) -N, N-di (tallowacyloxyethyl) ammonium methosulfate, methyl N- (2-hydroxyethyl) -N, N-di (palmacyloxyethyl) ammonium methosulfate or methyl N- (2-hydroxyethyl) -N, N-di (stearoyloxyethyl) methosulfate.
  • the trialkanolamine-based ester quat is a mixture of monoester compound, diester compound and triester compound.
  • a mixture of mono-, diester- and triester compounds has the best performance in terms of softness performance and scavenging of anionic residues, such as anionic surfactants, which have undesirably remained in the washing drum from the washing process.
  • the liquid fabric softening composition contains the softening mixture of trialkanolamine-based ester quat and trialkanolamine-based ester in an amount of from 0.5 to 40 wt%, more preferably in an amount of from 1 to 30 wt%, and more preferably in one Amount of 2 to 25 wt .-%, each based on the total liquid fabric softening composition. Most preferably, the amount of softening mixture is from 3 to 18% by weight, based on the total liquid fabric softening composition.
  • liquid fabric softening compositions contain from 2.4 to 14.4 weight percent trialkanolamine-based esterquat and from 0.6 to 3.6 weight percent trialkanolamine-based ester, based on the total liquid fabric softening composition.
  • the liquid fabric softening composition has a pH of less than 4, preferably less than 3.
  • the trialkanolamine-based ester is at least partially protonated. The best softness performance is achieved with a softening blend in which the trialkanolamine-based ester is fully protonated in the liquid fabric softening composition. It is preferred that the liquid fabric softening composition is a softener having a pH of less than 3.
  • the liquid fabric softening compositions may contain other ingredients which further enhance the performance and / or aesthetics of the liquid fabric softening composition.
  • preferred fabric softening compositions additionally contain one or more substances from the group of the further textile softening compounds, enzymes, electrolytes, non-aqueous solvents, pH adjusters, perfumes, perfume carriers, perfume microcapsules, fluorescers, dyes, soil release agents.
  • the fabric softeners of the present invention contain further fabric softening compounds, electrolytes, nonaqueous solvents, preservatives, pH adjusters, perfume, perfume microcapsules and / or dyes as further ingredients.
  • the liquid fabric softening compositions contain water as the main solvent.
  • a preferred further ingredient is another fabric softening compound which is especially a polysiloxane.
  • the use of polysiloxanes as further fabric softening compound is advantageous because they not only have a softening effect but also enhance the perfume impression on the laundry.
  • Polydimethylpolysiloxanes are known as efficient fabric care compounds.
  • Suitable polydimethysiloxanes include DC-200 (ex Dow Corning), Baysilone® M 50, Baysilone® M 100, Baysilone® M 350, Baysilone® M 500, Baysilone® M 1000, Baysilone® M 1500, Baysilone® M 2000 or Baysilone® M 5000 (all ex GE Bayer Silicones).
  • the polysiloxane contains the structural units a) and b).
  • a particularly preferred polysiloxane has the following structure: (CH 3 ) 3 Si - [O-Si (CH 3 ) 2 ] n - [O-Si (CH 3 ) ⁇ (CH 2 ) 3 -NH- (CH 2 ) 2 -NH 2 ⁇ ] x OSi (CH 3 ) 3 where the sum n + x is a number between 2 and 10,000.
  • Suitable polysiloxanes having the structural units a) and b) are for example commercially available under the trade names DC2-8663, DC2-8035, DC2-8203, DC05-7022 or DC2-8566 (all ex Dow Corning). Also suitable are, for example, the commercially available Dow Corning® 7224, Dow Corning® 929 Cationic Emulsion or Formasil 410 (GE Silicones).
  • perfume microcapsule liquid fabric softening compositions according to the present invention prolonged perfume impression on the laundry could be observed as compared to methanol containing liquid fabric softening compositions with perfume microcapsules.
  • the liquid fabric softening compositions can be used to condition fabrics.
  • the preparation of the liquid fabric softening compositions is carried out according to techniques familiar to those skilled in the art for the preparation of fabric softeners. This can be done for example by mixing the raw materials, optionally using high-shear mixing equipment. It is recommended to melt the trialkanolamine-based esterquat and the trialkanolamine-based ester followed by dispersing the melt in a solvent, preferably water. The other ingredients can be incorporated into the liquid fabric softening compositions by simple admixing.
  • Table 1 shows four fabric softening compositions E1 to E4 according to the invention and four fabric softening compositions V1 to V4 not according to the invention (data in% by weight of active substance).
  • Table 1 E1 E2 E3 E4 V1 V2 V3 V4 esterquat * 5.76 5.76 5.76 7.28 7.2 7.2 7.2 9.08 ester ** 1.44 1.44 1.44 1.8 - - - - 2-propanol 0.8 0.8 0.8 - 0.8 0.8 - 0.8 0.8 - ethanol - - - 1 - - - 1 polysiloxane *** 0.25 0.25 0.25 0.25 0.25 0.25 0.25 0.25 0.25 pH adjusters 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 MgCl 2 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 glycerin - - 18 - - 18 - dye + + + + + + + + + + + + + + + + + + + +
  • the amount of methanol in the non-inventive fabric softener compositions V1 to V4 was> 50 ppm #
  • the viscosity of the liquid fabric softening compositions was determined by means of a Brookfield RV DV II + P viscometer; Spindle 2 determined at 20 rpm and 20 ° C.
  • compositions E1 to E4 were storage stable for several weeks and showed no undesirable changes and only slight changes in viscosity or fluctuations during storage. To determine the storage stability, the compositions were stored in electronically controlled heating chambers under different climatic conditions. The storage time was 4 weeks. After 2 and 4 weeks, visual and olfactory matching of the fabric softening compositions and determination of the viscosity were carried out.

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  • 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)
EP13779188.5A 2012-10-19 2013-10-15 Textilweichmacherzusammensetzung mit trialkanolamin-basiertem esterquat Active EP2909294B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL13779188T PL2909294T3 (pl) 2012-10-19 2013-10-15 Kompozycja zmiękczająca tekstylia z esterquatem opartym na trialkanoloaminie

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102012219124.0A DE102012219124A1 (de) 2012-10-19 2012-10-19 Textilweichmacherzusammensetzung mit Trialkanolamin-basiertem Esterquat
PCT/EP2013/071455 WO2014060372A1 (de) 2012-10-19 2013-10-15 Textilweichmacherzusammensetzung mit trialkanolamin-basiertem esterquat

Publications (2)

Publication Number Publication Date
EP2909294A1 EP2909294A1 (de) 2015-08-26
EP2909294B1 true EP2909294B1 (de) 2018-01-31

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EP13779188.5A Active EP2909294B1 (de) 2012-10-19 2013-10-15 Textilweichmacherzusammensetzung mit trialkanolamin-basiertem esterquat

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US (1) US9458412B2 (pl)
EP (1) EP2909294B1 (pl)
DE (1) DE102012219124A1 (pl)
PL (1) PL2909294T3 (pl)
WO (1) WO2014060372A1 (pl)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2762509C1 (ru) * 2021-04-15 2021-12-21 Общество с ограниченной ответственностью "Синергетик" Композиция для умягчения тканей с ухаживающими добавками

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210106909A1 (en) 2019-06-27 2021-04-15 Benchmark Games International, Llc Arcade game with floor controller

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3638918A1 (de) * 1986-11-14 1988-05-26 Henkel Kgaa Quartaere ammoniumverbindungen, deren herstellung und verwendung als textilnachbehandlungsmittel
DE4338998A1 (de) * 1993-11-15 1995-05-18 Henkel Kgaa Quarternierte Fettsäuretrieethanolaminester
US6083899A (en) * 1996-09-19 2000-07-04 The Procter & Gamble Company Fabric softeners having increased performance
US20040097395A1 (en) * 2002-11-14 2004-05-20 Andre Crutzen Fabric softening composition containing esterquat with specific ester distribution and sequestrant
JP4461331B2 (ja) 2002-11-29 2010-05-12 チバ ホールディング インコーポレーテッド ホモ−および／もしくはコポリマーを含む繊維柔軟剤組成物
DE50305183D1 (de) * 2003-06-24 2006-11-09 Cognis Ip Man Gmbh Perlglänzende wässrige Zubereitungen
GB0602741D0 (en) * 2006-02-10 2006-03-22 Unilever Plc Fabric conditioning compositions
EP1939273A1 (en) * 2006-12-28 2008-07-02 Kao Corporation, S.A. Non-rinse fabric softener

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2762509C1 (ru) * 2021-04-15 2021-12-21 Общество с ограниченной ответственностью "Синергетик" Композиция для умягчения тканей с ухаживающими добавками

Also Published As

Publication number Publication date
PL2909294T3 (pl) 2018-07-31
WO2014060372A1 (de) 2014-04-24
US20150210959A1 (en) 2015-07-30
DE102012219124A1 (de) 2014-04-24
US9458412B2 (en) 2016-10-04
EP2909294A1 (de) 2015-08-26

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