WO1993013112A1 - Procede de blanchiment d'alkylglucosides et/ou d'alcenylglucosides - Google Patents

Procede de blanchiment d'alkylglucosides et/ou d'alcenylglucosides Download PDF

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Publication number
WO1993013112A1
WO1993013112A1 PCT/EP1992/002894 EP9202894W WO9313112A1 WO 1993013112 A1 WO1993013112 A1 WO 1993013112A1 EP 9202894 W EP9202894 W EP 9202894W WO 9313112 A1 WO9313112 A1 WO 9313112A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
bleaching
alkenyl
alcohol
stabilizers
Prior art date
Application number
PCT/EP1992/002894
Other languages
German (de)
English (en)
Inventor
Paul Schulz
Rainer Eskuchen
Herbert Esser
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.)
Filing date
Publication date
Priority claimed from DE19914142592 external-priority patent/DE4142592A1/de
Priority claimed from DE19924200850 external-priority patent/DE4200850A1/de
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1993013112A1 publication Critical patent/WO1993013112A1/fr

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Classifications

    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/42—Separation; Purification; Stabilisation; Use of additives
    • C07C303/44—Separation; Purification
    • 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
    • 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

Definitions

  • the invention relates to a process for bleaching alkyl and / or alkenyl oligoglycosides, in which the bleaching is carried out with peroxygen compounds in the presence of aluminum ions, alkali silicates, sugar acids and / or organic complexing agents as stabilizers.
  • European Patent EP 0 165 721 B1 suggests treating alkyl glycosides first with hydrogen peroxide or other peroxygen compounds and then with an SO 2 source.
  • a process for bleaching alkyl glucosides is known from European patent application EP 0 338 151 A1, in which the products are subjected to a hydrogenation, for example with sodium boranate.
  • the object of the invention was therefore to develop an improved process for bleaching alkyl and / or alkenyl oligoglyosides which is free from the disadvantages described.
  • the invention relates to a process for bleaching alkyl and / or alkenyl glycosides with the aid of peroxygen compounds, which is characterized in that the bleach is selected in the presence of stabilizers from the group consisting of aluminum ions, alkali metal silicates, sugar acids and organic complexing agents is formed.
  • stabilizers from the group consisting of aluminum ions, alkali metal silicates, sugar acids and organic complexing agents.
  • R! for an aliphatic, linear or branched alkyl and / or alkenyl radical with 6 to 22 carbon atoms
  • the glycose unit [G] can be derived from aldoses or ketoses. Because of the better reactivity, the reducing saccharides, the aldoses, are preferably used. Among the aldoses, glucose is particularly suitable because of their easy access and technical availability.
  • the preferred bleached alkyl and / or alkenyl oligoglycosides are therefore the alkyl and / or alkenyl oligoglucosides.
  • the alkyl radical R 1 can be derived from primary alcohols having 6 to 22, preferably 12 to 18, carbon atoms. Typical examples are capronic alcohol, caprylic alcohol, capric alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palm oleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, arachyl alcohol, technical alcohols, gadoleyl alcohol, and mixtures thereof, gadoleyl alcohol of natural fats and oils, for example palm oil, palm kernel oil, coconut oil or beef tallow.
  • capronic alcohol caprylic alcohol, capric alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palm oleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol,
  • alkyl oligoglycosides of the formula (I) in which R 1 is an alkyl radical having 12 to 18 carbon atoms. ato en, [G] stands for a glucose residue and / or p for numbers from 1.1 to 3.0.
  • the bleaching is carried out in the presence of peroxygen compounds.
  • peroxygen compounds Typical examples of this are perborates, percarbonates and in particular hydrogen peroxide, which can be used in the form of an aqueous 5 to 70, preferably 15 to 35% by weight solution.
  • concentration of the peroxygen compounds can be 1 to 5, preferably 2 to 3% by weight, based on the solids content of the alkyl or alkenyl oligoglycoside paste to be bleached.
  • Aluminum ions, alkali silicates, sugar acids and / or organic complexing agents come into consideration as stabilizers.
  • the aluminum ions can be added to the peroxygen compounds in the form of salts, for example sulfates, carbonates, silicates or phosphates.
  • alkali silicates are sodium and / or potassium silicates (“water glass”), in which an average of 2 to 4 moles of silicon dioxide per mole of alkali oxide.
  • sugar acids gluconic acid, glucaric acid, glucoronic acid and glucoheptonic acid and their alkali and alkaline earth salts are particularly suitable.
  • organic complexing agents are phosphonic acids, such as, for example, diethylenetriaminepentamethylphosphonic acid.
  • the stabilizers can be used individually or in combination in concentrations of 0.1 to 5.0, preferably 0.5 to 3.0 and in particular 1.0 to 2.0% by weight, based on the solids content of the alkyl to be bleached. or alkenyl oligoglycoside paste - are used.
  • the surface-active compounds are mixed with the peroxygen compounds and the stabilizers. This can take place at ambient temperature or else at the bleaching temperature, the latter being 80 to 120, preferably 90 to 100 ° C.
  • the alkyl or alkenyl oligoglycosides obtainable by the process according to the invention are light-colored and are suitable for the production of detergents, dishwashing detergents and cleaning agents and for products for hair and body care, in which they are present in amounts of 0.1 to 50, preferably 1 to 10 wt .-% - based on the agent - may be included.
  • the water of reaction was continuously distilled off and the reaction was stopped after the water separation had ended and the residual content of unreacted glucose in the mixture was less than 1% by weight, based on the starting amount.
  • the reaction mixture was then neutralized with magnesium oxide, the excess coconut fatty alcohol was separated off under reduced pressure (approx. 1 mbar) and at a temperature of 180 ° C. using a thin-film evaporator and the residue was pasted with water.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biochemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Detergent Compositions (AREA)

Abstract

Des alkylglucosides et/ou des alcénylglucosides de teinte claire sont fabriqués au moyen de composés peroxygénés, par blanchiment en présence d'agents stabilisants choisis dans le groupe formé par les ions aluminium, les silicates alcalins, les acides sacchariques et des agents complexants organiques.
PCT/EP1992/002894 1991-12-21 1992-12-14 Procede de blanchiment d'alkylglucosides et/ou d'alcenylglucosides WO1993013112A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DEP4142592.8 1991-12-21
DE19914142592 DE4142592A1 (de) 1991-12-21 1991-12-21 Verfahren zur bleiche oberflaechenaktiver verbindungen
DEP4200850.6 1992-01-15
DE19924200850 DE4200850A1 (de) 1992-01-15 1992-01-15 Verfahren zur bleiche von alkyl- und/oder alkenyloligoglycosiden

Publications (1)

Publication Number Publication Date
WO1993013112A1 true WO1993013112A1 (fr) 1993-07-08

Family

ID=25910447

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/EP1992/002895 WO1993013113A1 (fr) 1991-12-21 1992-12-14 Procede de blanchiment pour composes tensioactifs
PCT/EP1992/002894 WO1993013112A1 (fr) 1991-12-21 1992-12-14 Procede de blanchiment d'alkylglucosides et/ou d'alcenylglucosides

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/002895 WO1993013113A1 (fr) 1991-12-21 1992-12-14 Procede de blanchiment pour composes tensioactifs

Country Status (3)

Country Link
EP (1) EP0618922A1 (fr)
JP (1) JPH07502682A (fr)
WO (2) WO1993013113A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996001269A1 (fr) * 1994-07-06 1996-01-18 Henkel Kommanditgesellschaft Auf Aktien Procede de production d'agents tensioactifs de couleur claire
EP0775226B2 (fr) † 1994-08-10 2001-04-18 Woellner-Silikat Gmbh Utilisation d'un concentre d'agents stabilisants pour solutions aqueuses de blanchiment et de traitement a base de peroxyde d'hydrogene et/ou d'autres composes peroxo organiques et/ou inorganiques

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4432623A1 (de) * 1994-09-14 1996-03-21 Huels Chemische Werke Ag Verfahren zur Bleichung von wäßrigen Tensidlösungen
DE4432621A1 (de) * 1994-09-14 1996-03-21 Huels Chemische Werke Ag Verfahren zur Bleichung von Tensidlösungen
US5914433A (en) * 1997-07-22 1999-06-22 Uop Lll Process for producing polymer grade olefins

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0165721A1 (fr) * 1984-05-24 1985-12-27 A.E. Staley Manufacturing Company Régulation de couleur de glycosides
EP0301298A1 (fr) * 1987-07-18 1989-02-01 Henkel Kommanditgesellschaft auf Aktien Procédé de préparation de glucosides d'alkyle
EP0306652A1 (fr) * 1987-09-05 1989-03-15 Hüls Aktiengesellschaft Procédé pour la préparation de glucosides d'alkyle
EP0306650A1 (fr) * 1987-09-05 1989-03-15 Hüls Aktiengesellschaft Procédé pour la préparation d'alkylglycosides
EP0306651A1 (fr) * 1987-09-05 1989-03-15 Hüls Aktiengesellschaft Procédé pour la préparation d'oligoglucosides d'alkyl
EP0362671A1 (fr) * 1988-10-05 1990-04-11 Henkel Kommanditgesellschaft auf Aktien Procédé direct pour la préparation des alkylglycosides
EP0389753A2 (fr) * 1989-03-30 1990-10-03 Hüls Aktiengesellschaft Procédé de préparation d'alkylpolyglycosides

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3159657A (en) * 1961-05-19 1964-12-01 Henkel & Cie Gmbh Preparation of light-colored sulfonated fatty acids and fatty acid derivatives
US3354187A (en) * 1962-03-09 1967-11-21 Henkel & Cie Gmbh Bleaching dark-colored sulfonation products
DE1234709B (de) * 1964-01-15 1967-02-23 Henkel & Cie Gmbh Kontinuierliches Verfahren zum Bleichen saurer Sulfonierungsprodukte
DE3319591A1 (de) * 1983-05-30 1984-12-06 Henkel KGaA, 4000 Düsseldorf Verfahren zur gewinnung farbstabiler hellfarbiger waessriger salzpasten von waschaktiven (alpha)-sulfofettsaeureestern

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0165721A1 (fr) * 1984-05-24 1985-12-27 A.E. Staley Manufacturing Company Régulation de couleur de glycosides
EP0301298A1 (fr) * 1987-07-18 1989-02-01 Henkel Kommanditgesellschaft auf Aktien Procédé de préparation de glucosides d'alkyle
EP0306652A1 (fr) * 1987-09-05 1989-03-15 Hüls Aktiengesellschaft Procédé pour la préparation de glucosides d'alkyle
EP0306650A1 (fr) * 1987-09-05 1989-03-15 Hüls Aktiengesellschaft Procédé pour la préparation d'alkylglycosides
EP0306651A1 (fr) * 1987-09-05 1989-03-15 Hüls Aktiengesellschaft Procédé pour la préparation d'oligoglucosides d'alkyl
EP0362671A1 (fr) * 1988-10-05 1990-04-11 Henkel Kommanditgesellschaft auf Aktien Procédé direct pour la préparation des alkylglycosides
EP0389753A2 (fr) * 1989-03-30 1990-10-03 Hüls Aktiengesellschaft Procédé de préparation d'alkylpolyglycosides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996001269A1 (fr) * 1994-07-06 1996-01-18 Henkel Kommanditgesellschaft Auf Aktien Procede de production d'agents tensioactifs de couleur claire
US5858961A (en) * 1994-07-06 1999-01-12 Henkel Kommanditgesellschaft Auf Aktien Process for the production of light-colored surfactants
EP0775226B2 (fr) † 1994-08-10 2001-04-18 Woellner-Silikat Gmbh Utilisation d'un concentre d'agents stabilisants pour solutions aqueuses de blanchiment et de traitement a base de peroxyde d'hydrogene et/ou d'autres composes peroxo organiques et/ou inorganiques

Also Published As

Publication number Publication date
EP0618922A1 (fr) 1994-10-12
JPH07502682A (ja) 1995-03-23
WO1993013113A1 (fr) 1993-07-08

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