WO1996011936A1 - Procede de preparation d'oligoglycosides d'alkyle et/ou d'alcenyle de couleur claire - Google Patents

Procede de preparation d'oligoglycosides d'alkyle et/ou d'alcenyle de couleur claire Download PDF

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Publication number
WO1996011936A1
WO1996011936A1 PCT/EP1995/003929 EP9503929W WO9611936A1 WO 1996011936 A1 WO1996011936 A1 WO 1996011936A1 EP 9503929 W EP9503929 W EP 9503929W WO 9611936 A1 WO9611936 A1 WO 9611936A1
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Prior art keywords
alkyl
bleaching
acid
alkaline earth
alkenyl
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PCT/EP1995/003929
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German (de)
English (en)
Inventor
Karl Schmid
Michael Neuss
Manfred Weuthen
Michael Langen
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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.)
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Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to AU37455/95A priority Critical patent/AU3745595A/en
Publication of WO1996011936A1 publication Critical patent/WO1996011936A1/fr

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    • 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 a process for the preparation of light-colored alkyl and / or alkenyl oligoglycosides, in which aqueous pastes of the nonionic surfactants are added to bleach solutions which contain alkaline earth metal salts in addition to active oxygen compounds, and to certain pH conditions during and after the bleaching complies with.
  • Alkyl oligoglycosides in particular alkyl oligoglucosides, are nonionic surfactants which, due to their excellent detergent properties and high ecotoxicological compatibility, are becoming increasingly important.
  • the manufacture and use of these substances have recently been described in a number of review articles, of which the publications by H.Hensen in Skin Care Forum, 1, (Oct. 1992), D.Balzer and N.Ripke in Seifen ⁇ are representative oils-fat-waxes 118, 894 (1992) and B.Brancg in Soap-oils-fat-waxes 118, 905 (1992) should be mentioned. They are usually prepared from glucose and fatty alcohols, which are acetalized in the presence of acidic catalysts.
  • the catalyst is then neutralized with sodium hydroxide solution and magnesium oxide.
  • the fatty alcohol is used in a large excess.
  • the acetalization is therefore generally followed by a step in which the unreacted alcohol is separated off by distillation. Even with gentle distillation from the thin layer, however, the product becomes discolored, which makes bleaching necessary.
  • colored bodies can also be formed by oxidation of the pastes in the presence of atmospheric oxygen [cf. P. Heyns et al. in Appl. Chem. j> 9, 600 (1957), VJ Traynelis et al. in J.-A. Chem. Soc.
  • Hüls AG has also applied for a patent for various processes for bleaching alkyl glucosides:
  • EP-A 0306650, EP-A 0306651 and EP-A 0306652 propose treating the crude glucosides in the solvent with active carbon, which Separate solvent and bleach the distillation residue with hydrogen peroxide.
  • the documents EP-A 0389753 and EP-A 0526710 disclose processes in which the bleaching takes place using an ozone-containing gas mixture at a pH of 3 to 11 or by irradiation with a 100-1000 watt lamp.
  • the object of the invention was therefore to provide an improved process for the preparation of light-colored alkyl and / or alkenyl oligoglycoside pastes which are stabilized against microbial attack, according to which not only very light-colored but also temperature and la ⁇ stable products can be obtained.
  • the invention relates to a process for the preparation of light-colored alkyl and / or alkenyl oligoglycosides of the formula
  • R * for an alkyl and / or alkenyl radical with 4 to 22 carbon atoms
  • G for a sugar radical with 5 or 6 carbon atoms lenstoffatomen
  • p stands for numbers from 1 to 10, which is characterized in that one
  • the pH during the bleaching is adjusted to 9 to 11 by adding alkali and after the bleaching to a maximum of 11.5, preferably 10.5 to 11.2.
  • Alkyl and alkenyl oligoglycosides are known substances which can be obtained by the relevant processes in preparative organic chemistry.
  • 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 oligoglucosides.
  • the alkyl or alkenyl radical R 1 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capro 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 their technical mixtures, which can be obtained as described above.
  • Al ⁇ kyloligoglucoside are preferably based on hydrogenated Ci2 / 14- " ⁇ ° kosal- alcohol with a DP of 1 to 3
  • alkyl oligoglucoside pastes of the formula (I) are bleached, in which R 1 represents an alkyl radical having 8 to 18 carbon atoms.
  • the alkyl and / or alkenyl oligoglycoside pastes preferably have a water content of less than 50% by weight.
  • a particularly advantageous low viscosity of 100 to To achieve 500 mPas it has proven to be expedient to use a mixture of Cg-Cio- un ( ** - Ci2-C ⁇ g-alkyl oligoglucoside pastes.
  • the pastes can be used to further reduce the viscosity of hydrotropes such as, for example, toluenesulfonate, xylene sulfonate, cumene sulfonate , Butane sulfonate, C4-C ⁇ o * dicarboxylic acids or methyl, ethyl, propyl and / or butyl glucosides contain.
  • hydrotropes such as, for example, toluenesulfonate, xylene sulfonate, cumene sulfonate , Butane sulfonate, C4-C ⁇ o * dicarboxylic acids or methyl, ethyl, propyl and / or butyl glucosides contain.
  • Active oxygen compounds are to be understood as hypochlorites and substances which have a peroxide group. Typical examples are sodium hypochlorite on the one hand and sodium peroxide, sodium percarbonate, barium peroxide, performic acid, peracetic acid and the like on the other hand. Hydrogen peroxide is preferably used, a technical aqueous solution with an active substance content of 20 to 50 and in particular 25 to 35% by weight usually being used.
  • the alkaline earth metal salts in question are preferably selected from the group formed by magnesium oxide, magnesium hydroxide, magnesium methylate, calcium oxide and / or calcium hydroxide.
  • alkaline earth metal salts can be used, which are selected from the group consisting of Peroxide-soluble magnesium and / or calcium salts of formic acid, acetic acid, propionic acid, glycolic acid, lactic acid, gluconic acid, citric acid, benzoic acid, dodeylbenzenesulfonic acid, sulfosuccinic acid and / or p-toluenesulfonic acid.
  • Magnesium oxide and / or magnesium citrate is preferably used.
  • the bleaching agent solutions can contain the active oxygen compounds in a concentration of 20 to 50 and preferably 25 to 35% by weight and the alkaline earth metal salts in a concentration of 0.1 to 10, preferably 1 to 7% by weight. It has proven to be advantageous if the bleaching agent solution is freshly prepared, has a pH in the range from 3 to 9, preferably 7 to 8, and the paste is present in an amount of 0.1 to 5% by weight on the paste and the active substance content of the bleach solution.
  • the bleaching agent solutions can contain activators which are capable of forming persistent oxygen compounds. Typical examples are benzoic anhydride, pentaacetyl glucose, ethylenediaminetetraacetate and manganese compounds which are at least finely dispersible in the alkaline pH range. Bleaching process
  • the bleaching is usually carried out at a temperature in the range from 20 to 80 and preferably 50 to 70 ° C.
  • the alkyl and / or alkenyl oligoglycosides preferably have a solids content above 55, preferably above 60% by weight or a water content of below 45, preferably below 40% by weight.
  • This can include can be achieved by adding anhydrous additives such as, for example, 1 to 10% by weight of fatty alcohol polyglycol ether, 0.1 to 10% by weight of anionic and / or amphoteric surfactants or 0.1 to 5% by weight of inorganic salts to the pastes.
  • An increase in the active substance content is particularly advantageous in order to ensure adequate stabilization against microbial attack even at a pH of maximum 11.5. If necessary, it is also possible to add small amounts of ethanol.
  • the bleaching is carried out under protective gas and the bleached paste is filtered or centrifuged at about 80 ° C.
  • a particular advantage of the process is that it can also be used on aqueous pastes which have already been bleached.
  • the paste viscosity can usually be reduced by a power of ten. which without adversely affecting the thickenability by adding electrolyte salts.
  • aqueous pastes of the alkyl and / or alkenyl oligoglycosides obtainable by the process according to the invention are practically colorless and have proven to be extraordinarily color-stable even when stored at elevated temperature for a long time. They are suitable for the production of detergents, dishwashing detergents and cleaning products and products for hair and body care, in which they can be present in amounts of 1 to 50, preferably 5 to 25% by weight, based on the composition .
  • the pH of the paste - measured as a 20% by weight solution of nonionic surfactant in 15% by weight aqueous isopropyl alcohol - was adjusted to 11.5 by adding sodium hydroxide solution.
  • the paste was then stored for 5 days in a closed glass vessel at 90 ° C.
  • the Gardner color number after completion of the heat storage was 3.
  • Comparative example VI was repeated, but using a bleaching agent solution which additionally contained 0.8 g of magnesium oxide in dispersed solution. After bleaching for 3 hours, the Gardner color number was also 0.5. The paste was adjusted to pH 11.2 as described above. The paste was then stored in a sealed glass vessel at 90 ° C. for 5 days. The Gardner color number after completion of the heat storage was 1.
  • Comparative Examples VI were repeated, but using a bleach solution which had been prepared in the following manner: 0.8 g of magnesium oxide was dissolved in 5.6 g of a 50% by weight citric acid and then 10 g of a 35% by weight Hydrogen peroxide solution added. The bleaching agent solution was added to the paste in portions, the pH being kept in the range from 10.7 to 11.1. The Gardner number was also 0.5. Finally, the paste was again adjusted to a pH of 11.5 with sodium hydroxide solution and 2% by weight, based on the active substance content, of ethyl glucoside was added. The paste was then stored in a sealed glass vessel at 90 ° C. for 5 days. The Gardner color number after completion of the heat storage was 1.

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  • 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)
  • Detergent Compositions (AREA)
  • Saccharide Compounds (AREA)

Abstract

Selon un procédé amélioré de préparation d'oligoglycosides d'alkyle et/ou d'alcényle de couleur claire, (a) on prépare une solution de blanchiment qui contient des composés d'oxygène actif et des sels alcalino-terreux; et (b) on ajoute la solution de blanchiment à une pâte aqueuse d'oligoglycosides d'alkyle et/ou d'alcényle avec une teneur en matières solides comprise entre 40 et 70 % en poids et une viscosité selon Höppler dans une plage comprise entre 100 et 2.000 mPas à une température comprise entre 20 et 80 °C, à condition que la valeur de pH pendant le blanchiment soit ajustée entre 9 et 11 par adjonction d'alcali et, après le blanchiment, sur au maximum 11,5.
PCT/EP1995/003929 1994-10-14 1995-10-05 Procede de preparation d'oligoglycosides d'alkyle et/ou d'alcenyle de couleur claire WO1996011936A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU37455/95A AU3745595A (en) 1994-10-14 1995-10-05 Process for preparing light-coloured alkyl and/or alkenyl oligoglycosides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944436761 DE4436761A1 (de) 1994-10-14 1994-10-14 Verfahren zur Herstellung hellfarbiger Alkyl- und/oder Alkenyloligoglykoside
DEP4436761.9 1994-10-14

Publications (1)

Publication Number Publication Date
WO1996011936A1 true WO1996011936A1 (fr) 1996-04-25

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PCT/EP1995/003929 WO1996011936A1 (fr) 1994-10-14 1995-10-05 Procede de preparation d'oligoglycosides d'alkyle et/ou d'alcenyle de couleur claire

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AU (1) AU3745595A (fr)
DE (1) DE4436761A1 (fr)
WO (1) WO1996011936A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0306651A1 (fr) * 1987-09-05 1989-03-15 Hüls Aktiengesellschaft Procédé pour la préparation d'oligoglucosides d'alkyl
WO1991019723A1 (fr) * 1990-06-15 1991-12-26 Henkel Kommanditgesellschaft Auf Aktien Procede pour eclaircir des alkylglycosides tensioactifs decolores et pour traiter le produit blanchi
WO1994002494A1 (fr) * 1992-07-15 1994-02-03 Henkel Corporation Blanchiment en continu d'alkypolyglycosides
WO1994010374A1 (fr) * 1992-10-26 1994-05-11 Sca-Wifsta-Östrand Ab Methode de blanchiment au peroxyde de pate au sulfate
JPH06184973A (ja) * 1992-12-14 1994-07-05 New Oji Paper Co Ltd リグニンを含有するパルプの生物処理方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0306651A1 (fr) * 1987-09-05 1989-03-15 Hüls Aktiengesellschaft Procédé pour la préparation d'oligoglucosides d'alkyl
WO1991019723A1 (fr) * 1990-06-15 1991-12-26 Henkel Kommanditgesellschaft Auf Aktien Procede pour eclaircir des alkylglycosides tensioactifs decolores et pour traiter le produit blanchi
WO1994002494A1 (fr) * 1992-07-15 1994-02-03 Henkel Corporation Blanchiment en continu d'alkypolyglycosides
WO1994010374A1 (fr) * 1992-10-26 1994-05-11 Sca-Wifsta-Östrand Ab Methode de blanchiment au peroxyde de pate au sulfate
JPH06184973A (ja) * 1992-12-14 1994-07-05 New Oji Paper Co Ltd リグニンを含有するパルプの生物処理方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 018, no. 533 (C - 1259) 11 October 1994 (1994-10-11) *

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Publication number Publication date
AU3745595A (en) 1996-05-06
DE4436761A1 (de) 1996-04-18

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