EP0663920A1 - Sels d'alkyle- et/ou d'alcenyloligoglycoside-sulfate-ester - Google Patents

Sels d'alkyle- et/ou d'alcenyloligoglycoside-sulfate-ester

Info

Publication number
EP0663920A1
EP0663920A1 EP93920846A EP93920846A EP0663920A1 EP 0663920 A1 EP0663920 A1 EP 0663920A1 EP 93920846 A EP93920846 A EP 93920846A EP 93920846 A EP93920846 A EP 93920846A EP 0663920 A1 EP0663920 A1 EP 0663920A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
carbon atoms
radical
alkenyl
formula
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Withdrawn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
EP93920846A
Other languages
German (de)
English (en)
Inventor
Manfred Weuthen
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
Publication of EP0663920A1 publication Critical patent/EP0663920A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C07H15/10—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical containing unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical

Definitions

  • the invention relates to alkyl and / or alkenyl oligoglycoside ester sulfonate salts, a process for their preparation in which alkyl and / or alkenyl oligoglycosides are transesterified in the presence of alkaline catalysts with alpha-sulfocarboxylic acid lower alkyl ester salts and the use of these products for Manufacture of surfactants.
  • Alkyl oligoglycosides and especially alkyl oligoglucosides are nonionic surfactants, which have become increasingly important due to their excellent detergent properties and high ecotoxicological compatibility.
  • EP-A1 0 186 242 (Procter & Gamble) describes the sulfation of alkyl oligoglucosides in dimethylformamide with sulfur trioxide and EP-A1-0 363 601 (Hoechst) describes sulfation with a sulfur trioxide.
  • Amine complex known. Gas sulfonation of alkenyl glycosides in inert solvents is described in DE-Al 39 18 135 (Henkel).
  • the object of the invention was to develop new anionically modified alkyl and / or alkenyl oligoglucosides, the production of which is free from the disadvantages described.
  • the invention relates to alkyl and / or alkenyl oligoglycoside estersulfonate salts which are obtained by alkyl and / or alkenyl oligoglycosides of the formula (I),
  • R ⁇ for a linear or branched alkyl and / or alkenyl radical having 4 to 22 carbon atoms
  • G for one Sugar residue with 5 or 6 carbon atoms
  • p represents numbers from 1 to 10
  • R2 represents hydrogen or an alkyl radical having 1 to 20 carbon atoms
  • R 3 represents a linear or branched alkyl radical having 1 to 4 carbon atoms
  • X represents an alkali metal
  • anionically modified alkyl and / or alkenyl oligoglycosides can be obtained in high yields without the use of solvents if the alcohol component in alpha-sulfocarboxylic acid ester salts is exchanged for the alkyl and / or alkenyl oligoglucoside.
  • the invention further relates to a process for the preparation of alkyl and / or alkenyl oligoglycoside ester sulfonate salts, in which alkyl and / or alkenyl oligoglycosides of the formula (I),
  • R 1 for a linear or branched alkyl and / or alkenyl radical with 4 to 22 carbon atoms
  • G for a sugar radical with 5 or 6 carbon atoms and p for numbers of 1 to 10
  • alkaline catalysts with alpha-sulfocarboxylic acid lower alkyl ester salts of the formula (II) in the presence of alkaline catalysts with alpha-sulfocarboxylic acid lower alkyl ester salts of the formula (II),
  • R 2 represents hydrogen or an alkyl radical having 1 to 20 carbon atoms
  • R 3 represents a linear or branched alkyl radical having 1 to 4 carbon atoms
  • X represents an alkali metal
  • Alkyl and alkenyl oligoglycosides are known substances which can be obtained by the relevant processes in preparative organic chemistry. Representative of the extensive literature, reference is made here to the publications EP-Al-0 301 298 and WO 90/3977.
  • the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucos de.
  • the alkyl or alkenyl radical R- can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capronic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxo synthesis.
  • the alkyl or alkenyl radical R 1 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and the technical mixtures obtained as described above can. Alkyl oligoglucosides based on hardened Ci2 / 14 co- alcohol with a DP of 1 to 3 are preferred.
  • alpha-sulfocarboxylic acid n-edrigalkyl ester salts which are also referred to as "alkyl ester sulfonates”. They are usually prepared by sulfonating fatty acid lower alkyl esters, in particular fatty acid methyl esters with sulfur trioxide and subsequent neutralization.
  • Typical examples are sulfonates of esters of acetic acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, arachic acid, behenic acid and their technical mixtures with ethanol, propanol, butanol and especially methanol in the form of their sodium or potassium salts.
  • Alpha-sulfocarboxylic acid lower alkyl ester salts of the formula (II) are preferably used, in which R 2 represents hydrogen or alkyl radicals having 10 to 16 carbon atoms, R 3 represents a methyl group and X represents sodium.
  • Alpha-sulfococonut or alpha-sulfotallow fatty acid estersulfonate sodium salts are particularly preferred.
  • the alkyl and / or alkenyl oligoglycosides and the alpha-sulfocarboxylic acid lower alkyl ester salts can be used in a molar ratio of 1: 2 to 2: 1. Since the transesterification usually takes place only via the primary hydroxyl group of the alkyl and / or alkenyl oligoglycosides, it is advisable to use the reactants in approximately stoichiometric amounts of from 1: 1.2 to 1.2: 1.
  • Suitable alkaline catalysts are substances which are selected from the group formed by alkali and alkaline earth oxides, hydroxides, carbonates and bicarbonates. Typical examples are sodium hydroxide, sodium carbonate, potassium carbonate and potassium hydrogen carbonate.
  • the catalysts are preferably used as anhydrous salts in amounts of 0.1 to 5, in particular 1 to 3,% by weight, based on the glycoside.
  • the transesterification can be carried out at temperatures from 100 to 200, preferably 140 to 190 ° C. in a manner known per se. It is advisable to continuously remove the alcohol released during the reaction from the reaction equilibrium and to neutralize the alkaline catalyst after the reaction has ended.
  • the alkyl and / or alkenyl oligoglycoside ester sulfonate salts reduce the surface tension of the water, wet hard surfaces and promote the emulsification of otherwise immiscible phases. In addition, they are characterized by a high ecotoxicological and skin cosmetic compatibility.
  • Another object of the invention therefore relates to the use of alkyl and / or alkenyl oligoglycoside ester sulfonate salts for the production of surface-active agents, in particular washing, rinsing and cleaning agents and agents for hair and body care, in which the salts in Amounts of 1 to 50, preferably 10 to 35 wt .-% - based on the agent - may be included.
  • DP grade 1.2
  • potassium carbonate 223 g (0.6 mol) of methyl palmitate sulfonate sodium salt.
  • the temperature was increased from 140 to 180 ° C. in accordance with the reaction rate (methanol discharge). After a reaction time of 10 h, the product was cooled, neutralized and ground.
  • Example 5 Analogously to Example 3, 453 g (1.0 mol) of hexadecyl glucoside (DP grade 1.3) in the presence of 6.3 g of potassium carbonate with 720 g of a 25% by weight suspension of 1.0 mol of methyl acetate-sulfonate-Na- Transesterified salt in methanol. After working up, the crude product was dissolved in 1500 ml of methanol under reflux. After cooling to 0 ° C. and crystallization, 470 g of the product could be obtained by filtration.
  • Example 5 Example 5:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Biotechnology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Saccharide Compounds (AREA)
  • Detergent Compositions (AREA)

Abstract

On obtient des sels d'alkyle- et/ou d'alcényloligoglycoside-sulfate-ester, par transestérification d'alkyle- et/ou d'alcényloligoglycosides de la formule (I): R1-O[G]p, dans laquelle R1 désigne un reste alkyle et/ou alcényle linéaire ou ramifié ayant 4 à 22 atomes de carbone, G désigne un reste saccharose ayant 5 ou 6 atomes de carbone et p vaut des nombres compris entre 1 et 10, en présence de catalyseurs alcalins, avec des sels d'acide α-sulfocarboxylique-ester d'alkyle inférieur de la formule (II) dans laquelle R2 désigne l'hydrogène ou un reste alkyle ayant 1 à 20 atomes de carbone, R3 désigne un reste alkyle linéaire ou ramifié ayant 1 à 4 atomes de carbone et X représente un métal alcalin. Ces produits se prêtent à la fabrication d'une pluralité d'agents tensioactifs.
EP93920846A 1992-10-09 1993-09-30 Sels d'alkyle- et/ou d'alcenyloligoglycoside-sulfate-ester Withdrawn EP0663920A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4234019A DE4234019A1 (de) 1992-10-09 1992-10-09 Alkyl- und/oder Alkenyloligoglycosid-estersulfonat-Salze
DE4234019 1992-10-09
PCT/EP1993/002672 WO1994009018A1 (fr) 1992-10-09 1993-09-30 Sels d'alkyle- et/ou d'alcenyloligoglycoside-sulfate-ester

Publications (1)

Publication Number Publication Date
EP0663920A1 true EP0663920A1 (fr) 1995-07-26

Family

ID=6470036

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93920846A Withdrawn EP0663920A1 (fr) 1992-10-09 1993-09-30 Sels d'alkyle- et/ou d'alcenyloligoglycoside-sulfate-ester

Country Status (4)

Country Link
EP (1) EP0663920A1 (fr)
JP (1) JPH08502267A (fr)
DE (1) DE4234019A1 (fr)
WO (1) WO1994009018A1 (fr)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3808200A (en) * 1969-07-29 1974-04-30 Agriculture Hexitol,glucose and surcose esters of alpha-sulfo fatty acids
SU740756A1 (ru) * 1978-07-03 1980-06-15 Тульский Филиал Всесоюзного Научно- Исследовательского И Проектного Института Химической Промышленности Полиэтиленгликолевые эфиры сульфокарбоновых кислот как поверхностно активные вещества
DE4006841A1 (de) * 1990-03-05 1991-09-12 Henkel Kgaa Verfahren zur sulfierung alkylglycosidhaltiger gemische
JPH0499791A (ja) * 1990-08-13 1992-03-31 Kao Corp アルキルグリコシドのスルホン酸塩及びその製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9409018A1 *

Also Published As

Publication number Publication date
JPH08502267A (ja) 1996-03-12
WO1994009018A1 (fr) 1994-04-28
DE4234019A1 (de) 1994-04-14

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