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WO1995024377A1 - Concentres aqueux de faible viscosite d'agents tensioactifs de betaïne - Google Patents

Concentres aqueux de faible viscosite d'agents tensioactifs de betaïne Download PDF

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Publication number
WO1995024377A1
WO1995024377A1 PCT/EP1995/000756 EP9500756W WO9524377A1 WO 1995024377 A1 WO1995024377 A1 WO 1995024377A1 EP 9500756 W EP9500756 W EP 9500756W WO 9524377 A1 WO9524377 A1 WO 9524377A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
carbon atoms
range
formula
weight
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.)
Ceased
Application number
PCT/EP1995/000756
Other languages
German (de)
English (en)
Inventor
Ansgar Behler
Bernd Fabry
Günter Uphues
Rafael Pi Subirana
Joachim Bigorra Llosas
Oriol Ponsati Obiols
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 EP95912184A priority Critical patent/EP0749413A1/fr
Publication of WO1995024377A1 publication Critical patent/WO1995024377A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair

Definitions

  • the invention relates to a process for the preparation of low-viscosity aqueous concentrates of betaine surfactants, in which fatty acid amidoamines, which are optionally formed in situ, in the presence of viscosity regulators and polyols, and, if appropriate, free fatty acids or their salts with halocarboxylic acids or their salts condensed.
  • Betaines or amphoteric surfactants are extremely skin-friendly and have excellent cleansing properties. They are therefore particularly suitable for the assembly of a large number of surface-active products.
  • their preparation is based on tertiary amines which are reacted with sodium chloroacetate to form alkyl betaines.
  • the reaction of fatty acid aminoamides or imidazolines with sodium chloroacetate leads to the formation of amphoteric surfactants of the glycinate type; If acrylic acid esters are used as alkylating agents, they form Aminopropionates.
  • Compounds of the type mentioned are described in a large number of review articles, of which only Parf.Cosm.Arom. T0. r 67 (1986), HAPPI, 70, (Nov. 1986) and Soap Cos .Chem.Spec. 46, (Apr. 1990).
  • a particular concern in the production of betaines or amphoteric surfactants is to provide products with a solids content above 50% by weight, which are low-viscosity, preferably liquid at room temperature and can therefore be easily decanted or pumped.
  • DE-Al 3613944 (Th.Goldschmidt) describes a process for the production of flowable and pumpable betaine solutions containing at least 70% by weight of active substance, in which fatty acid amidoamines are reacted with ammonium salts of halocarboxylic acids and the Quaternization in an organic solvent, which may have a maximum of 20 wt .-% water. Following the formation of the betaine, the water is removed azeotropically and the ammonium halide is filtered off. Because of the high technical outlay, such a method can hardly be considered.
  • DE-Al 3641871 (Henkel) relates to a process for the production of low-viscosity amphoteric surfactants with solids contents in the range from 45 to 50% by weight, in which low-diamine imidazolines are quaternized with precise observance of certain addition and temperature conditions.
  • DE-Cl 37 26 322 Thi.Goldschmidt
  • a process for the production of concentrated, flowable, aqueous betaine solutions is also known, in which the dilute aqueous crude solution of the betaine is adjusted to the desired concentration by evaporation of water and previously or subsequently add such an amount of mineral acid that the pH of the solution is 1 to 4.5.
  • Such products are, however, to be assessed negatively with regard to their stability, in particular with regard to contamination, and are only, if at all, suitable for marketing.
  • DE-Al 3826554 (Th.Goldschmidt) relates to a process for the production of highly concentrated betaine surfactants which may contain lower alcohols, in which the quaternization is carried out in the presence of nonionic, water-soluble surfactants with a HLB value preferably carried out in the range from 14 to 20.
  • suitable nonionic surfactants are adducts of 10 to 250 mol of ethylene oxide with Cg-Cig fatty alcohols or fatty acid partial esters of glycerol or sorbitol of the same C chain length.
  • the object of the invention was therefore to provide aqueous solutions of betaine surfactants which are of low viscosity, i.e. are liquid at room temperature, have a solids content in the range from 50 to 60% by weight and are stabilized against contamination.
  • the invention relates to a process for the preparation of low-viscosity aqueous concentrates of betaine surfactants of the formula (I),
  • R ⁇ CO stands for an aliphatic acyl radical with 8 to 22 carbon atoms
  • R ⁇ and R ⁇ independently of one another for an alkyl radical with 1 to 4 carbon atoms
  • n and m independently of one another for numbers in the range from 1 to 5, with Solids contents in the range from about 50 to 60% by weight, in which fatty acid aminoamides of the formula (II),
  • R ⁇ ⁇ -CO stands for an aliphatic acyl radical with 8 to 22 carbon atoms
  • R ⁇ and R ⁇ independently of one another for an alkyl radical with 1 to 4 carbon atoms and n for numbers in the range from 1 to 5, in the presence of
  • viscosity regulators selected from the group formed by nonionic surfactants with an HLB value in the range from 6 to 12 and / or hydroxycarboxylic acids, b) polyols and optionally c) free fatty acids or their alkali salts
  • X represents a halogen
  • Y represents hydrogen or an alkali metal
  • m represents numbers in the range from 1 to 5.
  • aqueous betaine concentrates with solids contents in the range from 50 to 60% by weight can now be reliably obtained at room temperature.
  • the invention includes the knowledge that, in the sense of the invention, it is now also possible to obtain, directly, ie without isolation of the amidoamines, betaines by simultaneous transesterification and quaternization of mixtures of triglycerides and diamines which have the same advantageous properties award.
  • the concentrates prove to be adequately protected against antimicrobial attack even without the addition of preservatives.
  • the betaines are prepared by conventional processes by condensing fatty acid amidoamines with halogenated carboxylic acids.
  • fatty acid amidoamines instead of the fatty acid amidoamines, it is also possible to use directly mixtures of triglycerides and diamines which form fatty acid amidoamines in situ under reaction conditions and which are then quaternized. During the transesterification, glycerin is released, which is anyway necessary as a possible polyol component to set the desired viscosity and is therefore expressly desired as part of the mixture.
  • Another object of the invention therefore relates to a process in which triglycerides of the formula (IV) CH 2 0-COR 4
  • R 4 CO, R 5 CO and R 6 CO independently of one another represent aliphatic acyl radicals having 8 to 22 carbon atoms, with diamines of the formula (V),
  • R ⁇ and R ⁇ independently of one another are an alkyl radical having 1 to 4 carbon atoms and n is a number in the range from 1 to 5, in the presence of
  • viscosity regulators selected from the group formed by nonionic surfactants with an HLB value in the range from 6 to 12 and / or hydroxycarboxylic acids, b) polyols and optionally c) free fatty acids or their alkali salts
  • the starting materials for the production of the betaines of the formula (I) are either fatty acid amidoamines or mixtures of triglycerides and diamines - which form fatty acid amidoamines in situ.
  • Typical examples are fatty acid amidoamines derived from caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isosterainic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linoleic acid, linolenic acid stearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures, which, for example in the pressure splitting of natural fats and oils, in the reduction of aldehydes from Roelen's oxosynthesis or in the dimerization of unsaturated fatty acids.
  • Suitable triglycerides are natural, optionally hardened fats and oils such as, for example, palm oil, palm kernel oil, coconut oil, rapeseed oil from old and new cultivation, sunflower oil from old and new cultivation, olive oil, peanut oil, cottonseed oil, linseed oil and beef tallow.
  • Fatty acid amidoamines of the formula (II) or triglycerides of the formula (IV) are preferably used, in which R 4 CO or R 4 CO, R 5 CO and R 6 CO each represent acyl radicals having 8 to 18 carbon atoms.
  • Particularly preferred starting materials are fatty acid amidoamines or triglycerides based on coconut fatty acid or hardened or unhardened coconut oil.
  • the preferred fatty acid amidoamines or diamines also follow formulas (II) and (V), in which R 1 and R 2 each represent a methyl group and n and m independently of one another represent 2 or 3.
  • nonionic surfactants suitable as viscosity regulators are their HLB value, i.e. the degree of their hydrophilicity. It should be pointed out that the nonionic surfactants to be used according to the invention in the range of an HLB value of 6 to 12 are actually surface-active in the sense of the technical definition, i.e. significantly reduce the interfacial tension. In contrast to substances with significantly higher HLB values (for example highly ethoxylated sorbitan esters), there is a real interface effect in the sense of the invention, which must be distinguished from a simple dilution process.
  • Typical examples of suitable nonionic surfactants are addition products of an average of 1 to 8 mol of ethylene oxide onto fatty alcohols with 8 to 18 carbon atoms, such as, for example, C 2 /14-coconut fatty alcohol-2 EO adduct or Cg / ig-coconut fatty alcohol-7 EO adduct .
  • cos fatty acid monoglyceride which is sold by Henkel KGaA under the name Cetiol ( R ) HE.
  • preferred hydroxycarboxylic acids are aliphatic mono-, di- and / or tricarboxylic acids having 2 to 22, preferably 2 to 6 carbon atoms and 1, 2 or 3 hydroxyl groups.
  • Typical examples here are glycolic acid, lactic acid, malic acid, tartaric acid, citric acid, ricinoleic acid and 12-hydroxystearic acid and mixtures thereof.
  • the viscosity regulators are usually used in amounts such that a content of 1 to 10, preferably 1.5 to 3.0% by weight is obtained in the concentrates. Although the substances mentioned can also be added to the concentrates subsequently, it has proven to be advantageous to add the substances already during the condensation reaction. In a preferred embodiment of the invention, mixtures of ethoxylated partial glycerides and glycolic acid in a weight ratio of 4: 1 to 1: 4 are used as viscosity regulators. Polvole
  • Liquefying polyol compounds are:
  • Alkylene glycols such as ethylene glycol, ethylene glycol, propylene glycol;
  • Technical oligoglycerol mixtures with a degree of self-condensation of 1.5 to 10 such as technical diglycerol mixtures with a diglycerol content of 40 to 50
  • Methyl compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
  • Lower alkyl glucosides especially those with 1 to 8 carbons in the alkyl radical such as methyl and butyl glucoside;
  • sugar alcohols with 5 to 12 carbon atoms such as sorbitol or mannitol
  • the polyol compounds are usually used in amounts such that the betaine concentrate has a content of 1 to 10, preferably 1.5 to 3.0,% by weight. If one starts from triglycerides for the production of betaines or uses ethoxylated partial esters as nonionic surfactants, the mixtures already contain free glycerol through the transesterification or hydrolysis. This can be left as it is or increased if desired. Although liquefying it can also be advantageous to add the active polyols to the concentrates later, to add the substances also during the condensation reaction.
  • fatty acids are not necessary for the production of low-viscosity betaine concentrates. In most cases, however, a content of free fatty acids cannot be avoided, be it that fatty acids are released during the transesterification of the triglycerides or during the hydrolysis of the nonionic surfactants. As a rule, this content does not interfere, in some cases it may even be desirable because the application properties of the concentrates can be improved in this way. Since the products are finally made alkaline, the fatty acids are usually present as alkali salts.
  • Suitable fatty acids which can be added to the concentrates before the quaternization are those having 6 to 18 carbon atoms.
  • Typical examples are caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isosterainic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, ginoleic acid and arachic acid, arachic acid, arachic acid, arachic acid technical blends that are used, for example, in the pressure splitting of natural fats and oils, in the reduction of hyden accruing from Roelen's oxosynthesis or the dimerization of unsaturated fatty acids.
  • the proportion of fatty acids or their salts in the betaine concentrates can be 1 to 10, preferably 2 to 8 and in particular 5 to 6% by weight.
  • a content of 2 to 3% by weight often forms in situ and can be increased if desired.
  • Betaine concentrates with a solids content of, for example, 55% by weight and a coconut fatty acid content of 2.3% by weight which are distinguished by a particularly advantageous purification capacity, are obtained by simultaneously transesterifying and condensing a mixture of hardened coconut fat and aminopropyl-N, N-dimethylamine with sodium introduces such an amount of Cg / ⁇ o ⁇ Before l au ⁇ ett Text- acid, 2-ethylhexanoic acid, Isotridecylklare, isostearic and / or oleic acid, that the total free fatty acid content in the concentrate finally 5 to 6 wt .-% is.
  • traces of unreacted alkylating agents can be destroyed by adding ammonia, tertiary amines, alkanolamines, aminocarboxylic acids or protein hydrolyzates. Glycine or monoethanolamine are preferably used for this purpose.
  • the betaine concentrates according to the invention have a solids content of 50 to 60 and in particular 51 to 55% by weight, based on the concentrates.
  • the active substance content i.e. the betaine content is generally 8 to 12% by weight lower.
  • the content of free fatty acid aminoamide is usually less than 1 and in particular less than 0.5% by weight, the content of mono- or dichloroacetic acid in each case less than 5 ppm - based on the concentrates.
  • aqueous betaines according to the invention are also highly concentrated, liquid, stable in storage and have a minimized proportion of undesirable secondary constituents. They are particularly suitable for the production of surface-active agents of cleaning products and hair treatment and care products, in which they can be present in amounts of 1 to 30, preferably 2 to 10% by weight, based on the products.
  • Example 2 Analogously to Example 1, 483 kg of demineralized water, 55 kg of technical coconut fatty acid monoglyceride-7EO adduct (Cetiol ( R ) HE, Henkel KGaA, Düsseldorf / FRG) and 9 kg of glycolic acid were introduced, heated to 85 ° C. and with stirring with 101 kg Monochloroacetic acid and 31 kg of hardened coconut fatty acid amidopropyl-N, N-dimethylamine. 10 kg of coconut fatty acid, a further 280 kg of the amidoamine and 15 kg of monochloroacetic acid were then added, the mixture was adjusted to a pH of 9 and the mixture was stirred at 90 ° C. until the amine number had dropped to a value of 1.5 was. Working up was carried out according to Example 1. A low-viscosity product which was liquid at room temperature was also obtained.
  • Example 1 was repeated, but a total of 20 kg of glycolic acid and 15 kg of sorbitol were used instead of the Cetiol ( R ) HE. A low-viscosity product which was liquid at room temperature was also obtained.
  • Example 1 was repeated, but a total of 20 kg of glycolic acid and 15 kg of butylglucoside were used instead of the cetiol ( R) HE. A low-viscosity product which was liquid at room temperature was also obtained.
  • Example 1 was repeated, but instead of coconut fatty acid, 15 kg of Cg / 10 precursor fatty acid were added. A particularly low-viscosity product which was liquid at room temperature was obtained.
  • Example 1 was repeated, but the addition of the viscosity regulator was omitted. A solid paste was obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
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  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Des concentrés aqueux de faible viscosité d'agents tensioactifs de bétaïne, d'une teneur en matières solides comprise entre environ 50 et 60 % en poids, sont obtenus en condensant des aminoamides d'acides gras avec des acides carboxyliques halogénés ou avec leurs sels, en présence a) de régulateurs de viscosité choisis dans le groupe comprenant des agents tensioactifs non ioniques, de valeur HLB comprise entre 6 et 12, et/ou des acides hydroxycarboxyliques, b) de polyols et, le cas échéant, c) d'acides gras libres ou de leurs sels alcalins.
PCT/EP1995/000756 1994-03-11 1995-03-02 Concentres aqueux de faible viscosite d'agents tensioactifs de betaïne Ceased WO1995024377A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP95912184A EP0749413A1 (fr) 1994-03-11 1995-03-02 Concentres aqueux de faible viscosite d'agents tensioactifs de betaine

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944408228 DE4408228C2 (de) 1994-03-11 1994-03-11 Verfahren zur Herstellung niedrigviskoser wäßriger Betaintensidkonzentrate
DEP4408228.2 1994-03-11

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WO1995024377A1 true WO1995024377A1 (fr) 1995-09-14

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EP (1) EP0749413A1 (fr)
DE (1) DE4408228C2 (fr)
WO (1) WO1995024377A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0739878A1 (fr) * 1995-04-29 1996-10-30 Witco Surfactants GmbH Procédé pour la préparation de solutions aqueuses fluides concentrées de bétaine
US6207629B1 (en) 1996-11-05 2001-03-27 Kao Corporation Concentrated aqueous betaine-type surfactant compositions and process for their preparation
WO2001030744A1 (fr) * 1999-10-28 2001-05-03 Eoc Surfactants Nv Procede de preparation de solution de betaine concentree et fluide
US6475431B1 (en) * 1999-04-09 2002-11-05 Champion Technologies, Inc. Corrosion inhibitors with low environmental toxicity
US7297675B2 (en) * 2004-11-17 2007-11-20 Goldschmidt Gmbh Process for the preparation of highly concentrated flowable aqueous solutions of betaines

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9612067D0 (en) * 1996-06-10 1996-08-14 Smithkline Beecham Plc Composition
DE19738634A1 (de) * 1997-09-04 1999-03-11 Henkel Kgaa Niedrigviskose wäßrige Konzentrate von Alkylbetainen
DE10207924A1 (de) * 2002-02-23 2003-09-04 Clariant Gmbh Hochkonzentrierte wässrige Lösungen von Betainen oder Aminoxiden
FR2841836B1 (fr) 2002-07-04 2004-09-10 Faurecia Sieges Automobile Siege de vehicule automobile

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0353580A2 (fr) * 1988-08-05 1990-02-07 Th. Goldschmidt AG Procédé pour la préparation de solutions aqueuses fluides concentrées de bétaine
EP0560114A2 (fr) * 1992-03-09 1993-09-15 Th. Goldschmidt AG Solution aqueuse liquide d'une bétaine avec une teneur en solides d'au moins 40 % en poids

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3613944C1 (de) * 1986-04-24 1987-08-13 Goldschmidt Ag Th Verfahren zur Herstellung einer hochkonzentrierten,fliess- und pumpfaehigen Betainloesung
DE3726322C1 (de) * 1987-08-07 1988-12-08 Goldschmidt Ag Th Verfahren zur Herstellung konzentrierter fliessfaehiger waessriger Loesungen von Betainen

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0353580A2 (fr) * 1988-08-05 1990-02-07 Th. Goldschmidt AG Procédé pour la préparation de solutions aqueuses fluides concentrées de bétaine
EP0560114A2 (fr) * 1992-03-09 1993-09-15 Th. Goldschmidt AG Solution aqueuse liquide d'une bétaine avec une teneur en solides d'au moins 40 % en poids

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0739878A1 (fr) * 1995-04-29 1996-10-30 Witco Surfactants GmbH Procédé pour la préparation de solutions aqueuses fluides concentrées de bétaine
US6207629B1 (en) 1996-11-05 2001-03-27 Kao Corporation Concentrated aqueous betaine-type surfactant compositions and process for their preparation
US6683033B2 (en) 1996-11-05 2004-01-27 Kao Corporation Concentrated aqueous betaine surfactant compositions and process for their preparation
US6475431B1 (en) * 1999-04-09 2002-11-05 Champion Technologies, Inc. Corrosion inhibitors with low environmental toxicity
WO2001030744A1 (fr) * 1999-10-28 2001-05-03 Eoc Surfactants Nv Procede de preparation de solution de betaine concentree et fluide
US7297675B2 (en) * 2004-11-17 2007-11-20 Goldschmidt Gmbh Process for the preparation of highly concentrated flowable aqueous solutions of betaines

Also Published As

Publication number Publication date
DE4408228A1 (de) 1995-09-14
EP0749413A1 (fr) 1996-12-27
DE4408228C2 (de) 1997-02-20

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