EP1413623A1 - Compositions tensio-actives concentrées - Google Patents

Compositions tensio-actives concentrées Download PDF

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Publication number
EP1413623A1
EP1413623A1 EP02023572A EP02023572A EP1413623A1 EP 1413623 A1 EP1413623 A1 EP 1413623A1 EP 02023572 A EP02023572 A EP 02023572A EP 02023572 A EP02023572 A EP 02023572A EP 1413623 A1 EP1413623 A1 EP 1413623A1
Authority
EP
European Patent Office
Prior art keywords
preparations
alkyl
alkali
betaines
carbon atoms
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.)
Granted
Application number
EP02023572A
Other languages
German (de)
English (en)
Other versions
EP1413623B1 (fr
Inventor
Joaquin Bigorra Llosas
Nuria Dr. Bonastre Gilabert
Cristina Amela Conesa
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.)
Cognis IP Management GmbH
Original Assignee
Cognis Iberia SL
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 to AT02023572T priority Critical patent/ATE362507T1/de
Application filed by Cognis Iberia SL filed Critical Cognis Iberia SL
Priority to EP02023572A priority patent/EP1413623B1/fr
Priority to DE50210167T priority patent/DE50210167D1/de
Priority to ES02023572T priority patent/ES2286188T3/es
Priority to US10/532,283 priority patent/US20060110354A1/en
Priority to JP2004545845A priority patent/JP2006503943A/ja
Priority to PCT/EP2003/011366 priority patent/WO2004037963A1/fr
Publication of EP1413623A1 publication Critical patent/EP1413623A1/fr
Application granted granted Critical
Publication of EP1413623B1 publication Critical patent/EP1413623B1/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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/046—Salts
    • 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
    • C11D1/88—Ampholytes; Electroneutral 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/92—Sulfobetaines ; Sulfitobetaines
    • 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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/0094—Process for making liquid detergent compositions, e.g. slurries, pastes or gels

Definitions

  • the invention is in the field of surface-active substances and relates to aqueous preparations of amphoteric or zwitterionic surfactants, in particular betaines, which are characterized by a low paste viscosity despite a high concentration of active substance.
  • Amphoteric or zwitterionic surfactants are characterized by excellent foam and cleaning properties combined with excellent skin tolerance. They therefore serve as important raw materials for the production of detergents (e.g. manual dishwashing detergents) and cosmetics (e.g. hair shampoos).
  • the alkyl betaines preferably the alkyl amido betaines, have gained particular importance, the most important single product being undoubtedly cocamidopropyl betaine, which is commercially available, for example, under the name Dehyton® PK (Cognis).
  • Amphoteric or zwitterionic surfactants are marketed as aqueous preparations, the manufacturers' interest in particular being to sell concentrates, ie to keep the amount of water in the preparations as low as possible.
  • the active substance content cannot be increased arbitrarily, because the surface-active substances - depending on the other ingredients - start to form a lamellar gel-like phase above a value of about 40% by weight.
  • the associated extreme increase in viscosity which sometimes only occurs during storage, makes it practically impossible to convey or pump the substances. Such products are unsuitable for trade.
  • the object of the present invention was therefore to provide new concentrated aqueous amphoteric or zwitterionic surfactant preparations which, at an active substance concentration of, for example, 25 to 55% by weight, have a low Brookfield viscosity (20 ° C., spindle 1 , 10 rpm) of in particular less than 5,000 mPas and do not gel even during storage.
  • alkyl betaines examples include alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
  • alkyl betaines are the carboxyalkylation products of secondary and in particular tertiary amines which follow the formula (I) in which R 1 for alkyl and / or alkenyl radicals with 6 to 22 carbon atoms, R 2 for hydrogen or alkyl radicals with 1 to 4 carbon atoms, R 3 for alkyl radicals with 1 to 4 carbon atoms, q1 for numbers from 1 to 6 and Z for a Alkali and / or alkaline earth metal or ammonium.
  • Typical examples are the carboxymethylation products of hexylmethylamine, hexyldimethylamine, octyldimethylamine, decyldimethylamine, dodecylmethylamine, dodecyldimethylamine, Dodecylethylmethylamin, C 12/14 -Kokosalkyldimethylamin, myristyldimethylamine, cetyldimethylamine, stearyldimethylamine, stearyl, oleyl, C 16/18 tallow alkyl dimethyl amine and technical mixtures thereof.
  • Carboxyalkylation products of amidoamines which follow the formula (II) are also suitable, in which R 4 CO for an aliphatic acyl radical with 6 to 22 carbon atoms and 0 or 1 to 3 double bonds, R 5 for hydrogen or alkyl radicals with 1 to 4 carbon atoms, R 6 for alkyl radicals with 1 to 4 carbon atoms, q2 for numbers from 1 to 6, q3 for numbers from 1 to 3 and Z again represents an alkali and / or alkaline earth metal or ammonium.
  • R 4 CO for an aliphatic acyl radical with 6 to 22 carbon atoms and 0 or 1 to 3 double bonds
  • R 5 for hydrogen or alkyl radicals with 1 to 4 carbon atoms
  • R 6 for alkyl radicals with 1 to 4 carbon atoms
  • q2 for numbers from 1 to 6
  • q3 for numbers from 1 to 3
  • Z again represents an alkali and / or alkaline earth metal or ammonium.
  • Typical examples are reaction products of fatty acids with 6 to 22 carbon atoms, namely caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, gadoleic acid and arachic acid, arachic acid and their technical mixtures, with N, N-dimethylaminoethylamine, N, N-dimethylaminopropylamine, N, N-diethylaminoethylamine and N, N-diethylaminopropylamine, with sodium chloroacetate be condensed. It is preferred to use a condensation product of C 8/18 coconut fatty acid N, N-dimethylaminopropylamide with sodium chloroacetate.
  • Imidazolinium betaines are also suitable. These substances are also known substances which can be obtained, for example, by cyclizing condensation of 1 or 2 moles of fatty acid with polyhydric amines such as, for example, aminoethylethanolamine (AEEA) or diethylene triamine.
  • polyhydric amines such as, for example, aminoethylethanolamine (AEEA) or diethylene triamine.
  • AEEA aminoethylethanolamine
  • the corresponding carboxyalkylation products are mixtures of different open-chain betaines.
  • Typical examples are condensation products of the above-mentioned fatty acids with AEEA, preferably imidazolines based on lauric acid or again C 12/14 coconut fatty acid, which are subsequently betainized with sodium chloroacetate.
  • the alkali sulfates are customary inorganic salts, such as potassium or sodium sulfate, and mixtures thereof.
  • the use of sodium sulfate is preferred in terms of price and availability.
  • surface-active preparations is to be understood as meaning the aqueous pastes of the amphoteric or zwitterionic surfactants; In particular, they do not contain any other surface-active substances, but due to the production process, electrolyte salts, in particular sodium chloride, unreacted starting materials and, if appropriate, small amounts of free fatty acids or their salts.
  • the preparations can be alkaline or acidic, ie typically have a pH in the range from 6 to 9 or 1 to 6.
  • the content of amphoteric or zwitterionic surfactants, which is referred to as the "active substance content” can be in the range from 25 to 55% by weight, based on the preparation, and is generally 35 to 45% by weight.
  • the alkali sulfate content can be between 0.01 and 5, preferably 0.1 to 3 and in particular 0.5 to 1% by weight, likewise based on the preparation.
  • the amount of other ingredients which do not contribute to the surface-active nature of the preparation, especially electrolyte salts such as sodium chloride, is typically 5 to 10% by weight. This results in a usual water content of about 35 to about 60 and in particular 40 to 50% by weight.
  • the viscosity of such preparations is then Brookfield, measured in an RVT viscometer (20th ° C, spindle 1, 10 rpm) less than 5,000 mPas and is preferably in the range from 1,000 to 2,500 mPas.
  • a particular advantage of the present invention is that the alkali sulfates can be added both during production and afterwards; the latter can be preferred if you want to adjust the paste viscosity very precisely.
  • Another object of the present invention therefore relates to a process for the preparation of concentrated surface-active preparations with low viscosity, which is characterized in that fatty amines or fatty acid aminoamides are betainized in the presence of alkali metal sulfates with halocarboxylic acids or their alkali metal salts in a manner known per se.
  • alkali metal sulfates with halocarboxylic acids or their alkali metal salts
  • another object of the invention relates to a second process for the preparation of concentrated surface-active preparations with low viscosity, which is now characterized in that alkali sulfates are added to aqueous pastes of alkyl betaines and / or alkyl amido betaines.
  • alkali sulfates are added to aqueous pastes of alkyl betaines and / or alkyl amido betaines.
  • the amount of alkali sulfates is to be calculated in such a way that the final preparations have a content of 0.01 to 5, preferably 0.1 to 3 and in particular 0.5 to 1% by weight.
  • alkali sulfates especially sodium sulfate
  • alkyl betaine or alkyl amido betaine pastes to such an extent that they can be pumped and are eligible. It is irrelevant whether the addition is made during production or afterwards.
  • Another object of the present invention therefore relates to the use of alkali sulfates to reduce the viscosity of concentrated aqueous preparations of amphoteric or zwitterionic surfactants, the amount added - based on the preparations - from 0.01 to 5, preferably 0.1 to 3 and in particular 0 , 5 to 1 wt .-% can be.
  • the concentrates obtained in this way are suitable, for example, for the production of manual dishwashing detergents or hair shampoos, in which they can be present, for example, in amounts of 1 to 15 and in particular 3 to 8% by weight.
  • Comparative Example 1 was repeated, but the reaction of the coconut fatty acid with the N, N-dimethylaminopropylamine was repeated in the presence of 7.5 g (corresponding to 0.5% by weight, based on the final composition) of sodium sulfate. The mixture was again adjusted to an active substance concentration of 45% by weight with water and had a Brookfield viscosity (20 ° C., spindle 1, 10 rpm) of 4,500 mPas.

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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)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
EP02023572A 2002-10-23 2002-10-23 Compositions tensio-actives concentrées Expired - Lifetime EP1413623B1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP02023572A EP1413623B1 (fr) 2002-10-23 2002-10-23 Compositions tensio-actives concentrées
DE50210167T DE50210167D1 (de) 2002-10-23 2002-10-23 Konzentrierte grenzflächenaktive Zubereitungen
ES02023572T ES2286188T3 (es) 2002-10-23 2002-10-23 Preparaciones tensioactivas concentradas.
AT02023572T ATE362507T1 (de) 2002-10-23 2002-10-23 Konzentrierte grenzflächenaktive zubereitungen
US10/532,283 US20060110354A1 (en) 2002-10-23 2003-10-14 Concentrated surface-active preparations
JP2004545845A JP2006503943A (ja) 2002-10-23 2003-10-14 濃縮界面活性製剤
PCT/EP2003/011366 WO2004037963A1 (fr) 2002-10-23 2003-10-14 Preparations tensioactives concentrees

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP02023572A EP1413623B1 (fr) 2002-10-23 2002-10-23 Compositions tensio-actives concentrées

Publications (2)

Publication Number Publication Date
EP1413623A1 true EP1413623A1 (fr) 2004-04-28
EP1413623B1 EP1413623B1 (fr) 2007-05-16

Family

ID=32050000

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02023572A Expired - Lifetime EP1413623B1 (fr) 2002-10-23 2002-10-23 Compositions tensio-actives concentrées

Country Status (7)

Country Link
US (1) US20060110354A1 (fr)
EP (1) EP1413623B1 (fr)
JP (1) JP2006503943A (fr)
AT (1) ATE362507T1 (fr)
DE (1) DE50210167D1 (fr)
ES (1) ES2286188T3 (fr)
WO (1) WO2004037963A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1395286B1 (it) 2009-08-19 2012-09-05 Zschimmer & Schwarz Italiana S P A Soluzione acquosa concentrata di tensioattivo anfotero, particolarmente betaina, e procedimento per la sua preparazione
JP7233669B2 (ja) * 2017-05-22 2023-03-07 国立大学法人金沢大学 双性イオンを含む難溶性物質溶解剤

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0302329B1 (fr) 1987-08-07 1992-01-29 Th. Goldschmidt AG Préparation de bétaines en solution aqueuse concentrée fluide
WO1993025650A1 (fr) * 1992-06-16 1993-12-23 Henkel Corporation Compositions de concentres de tensioactifs a viscosite controlee
WO1995014076A1 (fr) * 1993-11-13 1995-05-26 Albright & Wilson Limited Compositions concentrees d'agents tensioactifs
EP0656346A1 (fr) * 1993-12-02 1995-06-07 Witco Surfactants GmbH Procédé pour la préparation des solutions des betaines qui sont fluxables et très concentrés
WO1999027048A1 (fr) * 1997-11-20 1999-06-03 Colgate-Palmolive Company Composition contenant des composes d'oxydes d'amine et de betaines
WO2001094524A2 (fr) 2000-06-06 2001-12-13 Huntsman International Llc Amido propyle betaine de coco (capb) hautement concentre

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4207386C2 (de) * 1992-03-09 1997-02-13 Goldschmidt Ag Th Wäßrige flüssige Lösung eines Betains mit mindestens 40 Gew.-% Festkörpergehalt

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0302329B1 (fr) 1987-08-07 1992-01-29 Th. Goldschmidt AG Préparation de bétaines en solution aqueuse concentrée fluide
WO1993025650A1 (fr) * 1992-06-16 1993-12-23 Henkel Corporation Compositions de concentres de tensioactifs a viscosite controlee
WO1995014076A1 (fr) * 1993-11-13 1995-05-26 Albright & Wilson Limited Compositions concentrees d'agents tensioactifs
EP0656346A1 (fr) * 1993-12-02 1995-06-07 Witco Surfactants GmbH Procédé pour la préparation des solutions des betaines qui sont fluxables et très concentrés
WO1999027048A1 (fr) * 1997-11-20 1999-06-03 Colgate-Palmolive Company Composition contenant des composes d'oxydes d'amine et de betaines
WO2001094524A2 (fr) 2000-06-06 2001-12-13 Huntsman International Llc Amido propyle betaine de coco (capb) hautement concentre

Also Published As

Publication number Publication date
US20060110354A1 (en) 2006-05-25
WO2004037963A1 (fr) 2004-05-06
DE50210167D1 (de) 2007-06-28
JP2006503943A (ja) 2006-02-02
ATE362507T1 (de) 2007-06-15
ES2286188T3 (es) 2007-12-01
EP1413623B1 (fr) 2007-05-16

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