EP0158869B1 - Utilisation des produits de condensation d'acide gras/hydroxyalkylpolyamine dans des compositions fluides contenant des détergents - Google Patents

Utilisation des produits de condensation d'acide gras/hydroxyalkylpolyamine dans des compositions fluides contenant des détergents Download PDF

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Publication number
EP0158869B1
EP0158869B1 EP85103454A EP85103454A EP0158869B1 EP 0158869 B1 EP0158869 B1 EP 0158869B1 EP 85103454 A EP85103454 A EP 85103454A EP 85103454 A EP85103454 A EP 85103454A EP 0158869 B1 EP0158869 B1 EP 0158869B1
Authority
EP
European Patent Office
Prior art keywords
weight
lustring
liquid compositions
fatty acid
agent
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.)
Expired - Lifetime
Application number
EP85103454A
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German (de)
English (en)
Other versions
EP0158869A3 (en
EP0158869A2 (fr
Inventor
Heinz-Manfred Wilsberg
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
Original Assignee
Henkel AG and Co KGaA
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
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to AT85103454T priority Critical patent/ATE58164T1/de
Publication of EP0158869A2 publication Critical patent/EP0158869A2/fr
Publication of EP0158869A3 publication Critical patent/EP0158869A3/de
Application granted granted Critical
Publication of EP0158869B1 publication Critical patent/EP0158869B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic 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
    • 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
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/667—Neutral esters, e.g. sorbitan esters
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • Liquid surfactant-containing compositions are used, for example, for washing textiles or as a shampoo for washing hair.
  • these compositions contain active ingredients that give the textiles or hair washed with them antistatic properties and fullness.
  • the most common active ingredients are quaternary, ammonia or imidazoline-derived cationic compounds that contain two long-chain C lü -C 24 groups in the molecule.
  • the cationic agents can only be used with great restrictions, since the effects of the cationic compounds with the anionic surfactants mutually impair one another; For this reason, such compositions usually contain exclusively nonionic surfactants, which are often selected in a special way to achieve an optimal combination of properties.
  • DE ⁇ PS ⁇ 28 17 834 relates, for example, to liquid compositions with special combinations of particularly selected nonionic surfactants and cationic active ingredients.
  • liquid compositions can be prepared, which contain up to 70% by weight of nonionic surfactants and, depending on the surfactant content, up to 35% by weight of quaternary ammonium compound. Up to 1/4 of the amount of the quaternary ammonium compound can be replaced by compounds derived from ammonia, for example by ditallow alkyldimethylammonium salts. ( DE-A-2855519).
  • compositions mentioned have good flowability at low temperatures and good storage stability at elevated temperatures, they lack the "consistency” that is a characteristic of the high active ingredient concentration for the consumer.
  • Consistency is understood to mean a viscosity of the compositions from 300 to 1,500 mPas in the range from +5 to + 40 ° C. combined with a turbidity.
  • This object is achieved according to the invention by the use of fatty acid / hydroxyalkyl polyamine condensation products as opacifiers and thickeners in the above-mentioned compositions.
  • Fatty acid / hydroxyalkyl polyamine condensation products (hereinafter referred to as fatty acid condensation products) are to be understood in the context of this invention as reaction products of triglycerides of higher fatty acids with hydroxyalkyl polyamines.
  • Suitable triglycerides of higher fatty acids are those with 16 to 24, preferably 16 to 22, carbon atoms in the fatty acid residues. If the glycerides contain fatty acid residues with 8 to 14 carbon atoms, the proportion of fatty acid residues with 16 to 22 carbon atoms in the mixed glycerides or glyceride mixtures should be at least 50%.
  • Hydroxyalkyl polyamines include compounds which have at least one hydroxyethyl, hydroxypropyl or dihydroxypropyl group and at least two hydrogen atoms bonded to nitrogen, e.g. Hydroxyethyl-ethylenediamine, dihydroxyethyl-ethylenediamine, hydroxyethyl-diethylenetriamine, hydroxypropyl-diethylenetriamine, etc. understood.
  • the fatty acid condensation products are obtained by reacting as many moles of the triglyceride with 1 mole of the hydroxyalkylpolyamine as fatty acid residues of the triglyceride can be bound in an amide and / or ester-like manner.
  • the condensation product can be acidified with inorganic or organic acids if necessary.
  • a particularly preferred product is made by reacting 1 mole of hardened beef tallow with 1 mole of hydroxyethylethylenediamine.
  • Remainder up to 100% by weight of water, monohydric or polyhydric alcohols, fragrances, dyes, preservatives, glazing agents and optionally other additives customary in liquid detergents.
  • Adducts of ethylene oxide and / or propylene oxide with fatty alcohols and / or with oxo alcohols or in particular mixtures of fatty alcohol ethoxylates with oxo alcohol ethoxylates are suitable as nonionic surfactants.
  • the remaining constituents of the compositions up to 100% by weight are water and organic solvents, especially mono- or polyvalent low-molecular alcohols (for example ethanol, isopropyl alcohol, 1,2-propylene glycol, amounts of glycerol from 1 to 20% by weight) liquid phase, also in small amounts of fragrances, dyes, preservatives, microbicides, brighteners, enzymes and foam regulating additives.
  • mono- or polyvalent low-molecular alcohols for example ethanol, isopropyl alcohol, 1,2-propylene glycol, amounts of glycerol from 1 to 20% by weight
  • fragrances for example ethanol, isopropyl alcohol, 1,2-propylene glycol, amounts of glycerol from 1 to 20% by weight
  • Formalin is usually used as a preservative for the liquid compositions in an amount of 0.05 to 1% by weight.
  • Brighteners for example, give the compositions a pearly sheen; a typical pearlescent agent is a commercially available mixture of ethylene glycol mono- or distearic acid esters, which has a particularly good effect in the compositions according to the invention.
  • the gloss agent is expediently incorporated in the form of a premix with nonionic surfactants, preferably with a portion of the nonionic surfactants a) of the compositions in a weight ratio of 3: 1 to 1: 3 and optionally with water.
  • the brightener, the surfactants and optionally the water are mixed together at a temperature above the melting temperature of the brightener, the mixture is then cooled to a temperature below the melting temperature of the brightener and the premix is mixed with the remaining surfactant at a temperature below the melting temperature of the brightener , the quaternary ammonium compound, the solvents and optionally the other constituents of the composition.
  • the compositions described are flowable and have a long shelf life in the range from +5 to + 40 ° C.
  • the liquid composition does not gel.
  • They can preferably be used for washing and simultaneously softening textiles made of wool or cotton, synthetic fibers such as polyester, polyacrylonitrile, polyamide and mixtures of wool or cotton and synthetic fibers.
  • the washing and softening process can be carried out either in the washing machine or by hand at washing temperatures up to about 60 ° C.
  • the application concentration of the agents is generally from 1 to 20 ml / l of wash liquor, preferably from 2 to 15 ml / l.
  • the detergents are characterized by the fact that they clean the textiles perfectly and at the same time give them a pleasant feel and anti-electrostatic properties. When washing by hand in the sink, they form a dense, pleasant foam; when washing in the washing machine, no foaming is observed. The foam can also be easily rinsed out.
  • the following examples describe the consistency of a fatty acid condensation product in liquid detergents based on nonionic surfactants and quaternary imidazolinium compounds with two long-chain alkenyl radicals.
  • the fatty acid condensation product was obtained by reacting 1 mol of hardened beef tallow with 1 mol of hydroxyethylethylenediamine at 90 to 100 ° C. in accordance with DE-PS 19 22 047.
  • Examples 1 to 3 are comparative examples of Prior art detergents without a fatty acid condensation product;
  • Examples 4 to 7 are examples of the present invention.
  • the data for the consistency apply to detergents stored for a week, since the viscosity can change slightly in the first days after the detergent mixtures have been prepared.
  • the viscosity was determined using a Brookfield RVT rotary viscometer with spindle 2 at 20 ° C. and 20 revolutions per minute. All detergents contained 0.1% by weight of formalin, 30% for preservation. The remainder of the recipes in Table 1, which add up to 100% by weight, is water. All concentration data in Table 1 are% by weight.
  • the detergents according to the invention were all still flowable at + 5 ° C; at + 40 ° C they were stable in storage. They all have a desired cloudiness or pearlescent.
  • the agents without a fatty acid condensation product (Examples 1 to 4) were clear and / or no longer flowable at + 5 ° C and / or unstable at + 40 ° C.
  • the textiles washed with it made of different fiber materials had a much softer and fuller feel than comparable detergents with the same composition and no softening agent. The foam formed during washing was surprisingly easily rinsed out practically completely.

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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)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Claims (9)

1. Utilisation d'un produit de condensation acide gras/hydroxy alcoyl polyamine en tant qu'agent de trouble et agent épaississant dans des compositions dépourvues d'agent tensio-actif anionique, liquides contenant des composés d'ammonium quaternaire assouplissants du textile, caractérisées en ce qu'elles contiennent:
a) de 10 à 40% en poids d'un agent tensio-actif non ionique,
b) de 1 à 15% en poids de composés d'ammonium quaternaire, en particulier des dérivés de l'imidazolinium,
c) de 0,4 à 5% en poids d'un produit de condensation acide gras/hydroxy alcoyl polyamine,
le reste à 100% en poids: eau, alcools mono- ou polyvalents, parfums, colorants, agents conservateurs, agents de brillance et éventuellement des additifs usuels dans les détergents liquides par ailleurs, comme par exemple des microbicides, des enzymes et des additifs pour contrôler la mousse.
2. Utilisation selon la revendication 1 dans des compositions liquides, qui contiennent en tant que dérivés d'ammonium quaternaire, des dérivés d'imidazolinium ayant deux radicaux alcoyl ou de préférence alcényle, en C10 à C24.
3. Utilisation selon l'une des revendications 1 et 2 dans les compositions liquides avec un dérivé d'imidazolinium qui contient deux radicaux oleyle.
4. Utilisation selon l'une des revendications 1 à 3, dans des compositions liquides qui contiennent comme agents tensio-actifs non-ioniques, des composés d'addition de l'oxyde d'éthylène et/ou de l'oxyde de propylène sur des alcools gras et/ou des oxoalcools ou de préférence des mélanges d'éthoxylates d'alcools gras et d'oxoalcools..
5. Utilisation selon l'une des revendications 1 à 4 dans des compositions liquides qui contiennent comme agent de brillance un mélange d'esters mono-stéariques ou distéariques d'éthylène glycol.
6. Utilisation selon l'une des revendications 1 à 5 dans des compositions liquides dans lesquelles on a introduit, d'une façon homogène, à une température en-dessous de la température de fusion de l'agent de brillance, l'agent de brillance sous la forme d'un pré-mélange avec des agents tensio-actifs non ioniques dans un rapport allant de 3:1 à 1:3, et le cas échéant avec de l'eau, obtenu par mélange de l'agent de brillance, de l'agent tensio-actif non ionique et le cas échéant de l'eau, à une température au-dessus de la température de fusion de l'agent de brillance et ensuite refroidissement à une température inférieure à la température de fusion de l'agent de brillance.
7. Utilisation selon l'une des revendications 1 à 6, dans des compositions liquides auxquelles on a ajouté l'agent de brillance sous forme d'un pré-mélange avec au moins une partie de l'agent tensioactif non-ionique a) de la composition et éventuellement avec de l'eau.
8. Utilisation selon l'une des revendications 1 à 7 dans des compositions liquides qui contiennent:
a) de 15 à 40% en poids d'agents tensio-actifs non ioniques,
b) de 5 à 15% en poids de dérivés d'imidazolinium,
c) de 0,5 à 3% en poids d'un produit de condensation d'acide gras/hydroxy alcoyl polyamine,
d) de 5 à 15% en poids d'alcools mono- ou polyvalent ayant de 2 à 4 atomes de carbone,
e) de 0,2 à 3,0% en poids d'agent de brillance,
le reste à 100% en poids: eau, parfum, colorant, agent conservateur, additifs pour contrôler la mousse, enzymes.
9. Utilisation selon les revendications 1 à 8, dans des compositions liquides qui contiennent:
a) de 15 à 40% en poids d'un mélange 1:1 de oxoalcool en C,4-C,5+7 mol d'oxyde d'éthylène et d'alcool gras en C10―C12+6 mol d'oxyde d'éthylène,
b) de 5 à 15% en poids de méthosulfate de 1-méthyl 1-oleylamido éthyl-2-oleyl-imidazolinium,
c) de 0,5 à 3% en poids d'un produit de condensation d'acide gras hydroxy alcoyl polyamine,
d) de 4 à 9% en poids de propylène glycol-1,2 et 1 à 6% en poids d'éthanol,
e) de 0,2 à 3% en poids d'un mélange d'esters mono- ou distéariques d'éthylène glycol,
le reste pour 100% en poids: eau, ainsi que en petites quantités, du parfum, un colorant, un agent conservateur, des additifs pour contrôler la mousse, des enzymes.
EP85103454A 1984-03-31 1985-03-23 Utilisation des produits de condensation d'acide gras/hydroxyalkylpolyamine dans des compositions fluides contenant des détergents Expired - Lifetime EP0158869B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85103454T ATE58164T1 (de) 1984-03-31 1985-03-23 Verwendung von fettsaeure/hydroxyalkylpolyaminkondensationsprodukten in fluessigen tensidhaltigen zusammensetzungen.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3412090 1984-03-31
DE19843412090 DE3412090A1 (de) 1984-03-31 1984-03-31 Verwendung von fettsaeure/hydroxyalkylpolyamin-kondensationsprodukten in fluessigen tensidhaltigen zusammensetzungen

Publications (3)

Publication Number Publication Date
EP0158869A2 EP0158869A2 (fr) 1985-10-23
EP0158869A3 EP0158869A3 (en) 1987-12-23
EP0158869B1 true EP0158869B1 (fr) 1990-11-07

Family

ID=6232262

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85103454A Expired - Lifetime EP0158869B1 (fr) 1984-03-31 1985-03-23 Utilisation des produits de condensation d'acide gras/hydroxyalkylpolyamine dans des compositions fluides contenant des détergents

Country Status (5)

Country Link
US (1) US4623471A (fr)
EP (1) EP0158869B1 (fr)
AT (1) ATE58164T1 (fr)
DE (2) DE3412090A1 (fr)
ES (1) ES541758A0 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4661269A (en) * 1985-03-28 1987-04-28 The Procter & Gamble Company Liquid fabric softener
DE3639322A1 (de) * 1986-11-17 1988-05-26 Henkel Kgaa Verfahren zur reinigung und desinfektion von endoskopen und mittel zur durchfuehrung des verfahrens
US5223166A (en) * 1986-11-17 1993-06-29 Henkel Kommanditgesellschaft Auf Aktien Preparations and processes for cleaning and disinfecting endoscopes
DE3706664A1 (de) * 1987-02-28 1988-09-08 Henkel Kgaa Fluessige textilbehandlungsmittel
JPH0768669B2 (ja) * 1990-10-05 1995-07-26 花王株式会社 濃縮型柔軟仕上剤
DE4125025A1 (de) * 1991-07-29 1993-02-04 Henkel Kgaa Fluessiges waschmittel
US5445747A (en) * 1994-08-05 1995-08-29 The Procter & Gamble Company Cellulase fabric-conditioning compositions
DE19511572C2 (de) * 1995-03-29 1998-02-26 Henkel Kgaa Niedrigviskose Trübungsmittelkonzentrate
WO2011112912A1 (fr) * 2010-03-12 2011-09-15 The Procter & Gamble Company Gélifiant d'amidon à ph réglable utilisable dans des compositions de produit de consommation

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1922047C3 (de) * 1969-04-30 1978-03-30 Henkel Kgaa, 4000 Duesseldorf Nachspülmittel für gewaschene Wäsche
DK131638A (fr) * 1969-06-07
US3959157A (en) * 1973-06-04 1976-05-25 Colgate-Palmolive Company Non-phosphate detergent-softening compositions
DE2529444C3 (de) * 1975-07-02 1982-04-15 Blendax-Werke R. Schneider Gmbh & Co, 6500 Mainz Flüssiges Feinwaschmittel
DE2539349C2 (de) * 1975-09-04 1985-04-11 Hoechst Ag, 6230 Frankfurt Wäschenachbehandlungsmittel
US4214997A (en) * 1977-10-26 1980-07-29 Lever Brothers Company Soil-release compositions
US4140641A (en) * 1978-03-17 1979-02-20 Colgate-Palmolive Company Concentrated liquid detergent with fabric softener
DE2817834C2 (de) * 1978-04-24 1983-05-19 Henkel KGaA, 4000 Düsseldorf Flüssiges Waschmittel
DE2966013D1 (en) * 1979-01-11 1983-09-01 Procter & Gamble Concentrated fabric softening composition
DE2918364A1 (de) * 1979-05-07 1980-11-20 Henkel Kgaa Waschmittel fuer textilien
DE2925859A1 (de) * 1979-06-27 1981-01-22 Henkel Kgaa Waeschenachbehandlungsmittel
DE3129549A1 (de) * 1981-07-27 1983-02-10 Henkel KGaA, 4000 Düsseldorf Mittel zum nachbehandeln gewaschener waesche in einem waeschetrockner
US4446042A (en) * 1982-10-18 1984-05-01 The Procter & Gamble Company Brightener for detergents containing nonionic and cationic surfactants

Also Published As

Publication number Publication date
DE3412090A1 (de) 1985-10-24
US4623471A (en) 1986-11-18
ATE58164T1 (de) 1990-11-15
EP0158869A3 (en) 1987-12-23
ES8603283A1 (es) 1985-12-16
ES541758A0 (es) 1985-12-16
EP0158869A2 (fr) 1985-10-23
DE3580383D1 (de) 1990-12-13

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