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WO1992000945A1 - Glycolethers insatures de polyalcylene - Google Patents

Glycolethers insatures de polyalcylene Download PDF

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Publication number
WO1992000945A1
WO1992000945A1 PCT/EP1991/001192 EP9101192W WO9200945A1 WO 1992000945 A1 WO1992000945 A1 WO 1992000945A1 EP 9101192 W EP9101192 W EP 9101192W WO 9200945 A1 WO9200945 A1 WO 9200945A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyalkylene glycol
unsaturated polyalkylene
alkoxylation
ether
hydrogen
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/EP1991/001192
Other languages
German (de)
English (en)
Inventor
Hans-Christian Raths
Bert Gruber
Dimitrios Ouzounis
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 WO1992000945A1 publication Critical patent/WO1992000945A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/02—Preparation of ethers from oxiranes
    • C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups

Definitions

  • the invention relates to unsaturated polyalkylene glycol ethers obtainable by reacting octadienylglycerol ethers with alkylene oxides, a process for their preparation and their use as surface-active agents.
  • unsaturated polyalkylene glycols are liquid or low-viscosity and can be easily processed without excessive heating. They are characterized by excellent emulsifier properties and excellent cleaning action and are therefore used for the production of cosmetic preparations, such as. B. oil bath emulsions, make-up creams, intensive hair treatment or cold wave emulsions [Seif., Oils, fats, waxes, 109, 225 (1983)].
  • the invention relates to unsaturated polyalkylene glycol ethers, obtainable by reacting octadienylglycerol ethers of the formula (I)
  • R * is an aliphatic hydrocarbon radical having 8 carbon atoms and 2 double bonds
  • R 2 and R 3 independently of one another are R 1 or hydrogen and the condition applies that at least one of the two radicals R 2 and 3 must be hydrogen in the presence of a Alkoxylation catalyst with 1 to 20 moles of alkylene oxide per mole of glycerol ether.
  • the invention includes the knowledge that the products according to the invention have good foam, wetting, washing and cleaning properties.
  • Unsaturated polyalkylene glycol ethers within the meaning of the invention which have particularly advantageous performance properties are obtained by reacting monooctadienylglycerol ethers with 2 to 7 moles of ethylene oxide per mole of glycerol ether in the presence of sodium ethylate, sodium hydroxide or hydrotalcite as the alkoxylation catalyst.
  • Octadienylglycerol ethers serve as starting products for the preparation of the unsaturated polyalkylene glycol ethers according to the invention, which in turn represent known substances and can be obtained by the relevant methods of preparative organic chemistry. They are produced from glycerol, which is reacted with 1,3-butadiene in the presence of palladium and triphenylphosphine [DE-B-1807 491]. The octadienylglycerol ethers are obtained as a mixture of the mono-, di- and triether, and their relationship to one another can be influenced by the type and concentration of the catalyst system and the choice of solvent.
  • the aim is to produce the purest possible monooctadienylglycerol polyalkylene glycol ether, it is advisable to fractionate the technical glycerol ether by distillation. In any case, it is advisable to use the 1,3-butadiene in the alkoxylation before the glycerol ether is used in the alkoxylation Separate by-product formed octatriene by distillation.
  • the invention further relates to a process for the preparation of unsaturated polyalkylene glycol ethers, characterized in that octadienylglycerol ethers of the formula (I)
  • R * stands for an aliphatic hydrocarbon radical with 8 carbon atoms and 2 double bonds
  • R 2 and R 3 independently of one another represent R 1 or hydrogen and the condition applies that at least one of the two radicals R 2 and R 3 represents hydrogen must stand, in the presence of an alkoxylation catalyst with 1 to 20 moles of alkylene oxide per mole of glycerol ether.
  • the reaction of hydroxy compounds with alkylene oxides is a large-scale process known per se.
  • the reaction is carried out in the presence of alkoxylation catalysts which can be acidic or basic in nature and can be soluble or insoluble in the reaction product. It has proven advantageous if the alkoxylation in the presence of 0.1 to 5, preferably 0.3 to 1.5 wt .-%, based on the sum of the starting materials, of an alkoxylation catalyst selected from the group consisting of Al - Potassium alkylates with 1 to 4 carbon atoms, for example sodium methylate or potassium tert-butoxide, alkali metal hydroxides, for example sodium hydroxide, alkaline earth metal phenates, such as strontium phenolate, alkaline earth metal phosphates, such as, for. B. barium phosphate and hydrotalcite is formed.
  • hydrotalcite which leads to products with a low residual content of free glycerol ether and a narrow homolog distribution, is particularly preferred.
  • the alkoxylation can be carried out using ethylene oxide and / or propylene oxide (in random or block distribution), one mole of the glycerol being reacted with an average of 1 to 20, preferably 2 to 7, moles of the alkylene oxide. Since the alkoxylation does not provide a uniform product, the ratio of glycerol ether and alkylene oxide only reflects the average degree of alkoxylation. If glycerol ethers which have more than one free hydroxyl group are used in the alkoxylation, the alkylene oxide is more or less statistically distributed over them.
  • the alkoxylation is carried out at temperatures from 100 to 180 ° C and pressures from 1 to 5 bar. To achieve an optimal reaction rate, it is advisable to work at temperatures of at least 150 ° C. Temperatures above 180 ° C. can place a high thermal load on the reaction products and, if appropriate, lead to undesirable discoloration and decomposition.
  • the unsaturated polyalkylene glycol ethers according to the invention are notable for a marked reduction in the surface tension of the water and also promote the wetting of solid interfaces
  • Water are also suitable for emulsifying oils and fats in aqueous systems and can increase the washing power of anionic and nonionic surfactants.
  • the invention therefore also relates to the use of the unsaturated polyalkylene glycol ethers according to the invention as surface-active
  • Example 2 Octadienyl ether + 5 moles of ethylene oxide.
  • Example 2 was repeated using 1.3 g of hydrotalcite as the alkoxylation catalyst. Following the reaction and working up, the catalyst was separated off by filtration. 380 g of a slightly yellow colored liquid were obtained.
  • the ether produced with hydrotalcite as the alkoxylation catalyst showed a lower free glycerol ether content and a significantly narrower homolog distribution.

Landscapes

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

Abstract

On produit des glycoléthers insaturés de polyalcylène, ayant des propriétés tensioactives, par réaction avec des oxydes d'alcylène d'éthers d'octadiénylglycérine de formule (I), dans laquelle R1 représente un reste hydrocarbure aliphatique avec 8 atomes de carbone et deux liaisons doubles, R2 et R3 représentent indépendamment l'un de l'autre R1 ou hydrogène, à condition qu'au moins un des deux restes R2 et R3 désigne hydrogène.
PCT/EP1991/001192 1990-07-05 1991-06-26 Glycolethers insatures de polyalcylene Ceased WO1992000945A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4021478A DE4021478A1 (de) 1990-07-05 1990-07-05 Ungesaettigte polyalkylenglycolether
DEP4021478.8 1990-07-05

Publications (1)

Publication Number Publication Date
WO1992000945A1 true WO1992000945A1 (fr) 1992-01-23

Family

ID=6409737

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1991/001192 Ceased WO1992000945A1 (fr) 1990-07-05 1991-06-26 Glycolethers insatures de polyalcylene

Country Status (2)

Country Link
DE (1) DE4021478A1 (fr)
WO (1) WO1992000945A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0586323A1 (fr) * 1992-07-20 1994-03-09 Kao Corporation, S.A. Composition détergente et méthode pour sa fabrication
US5403509A (en) * 1992-07-20 1995-04-04 Kao Corporation, S.A. Detergent composition comprising a mono-, di- and tri-ester mixture and method of manufacturing same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19500688A1 (de) * 1995-01-12 1996-07-18 Henkel Kgaa Nichtionische Tenside
JP3828370B2 (ja) 2000-05-31 2006-10-04 花王株式会社 モノアルキルエーテルの製法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4241224A (en) * 1979-10-09 1980-12-23 Basf Wyandotte Corporation Fiber lubricants derived from the oxyalkylation of a glycerol-1,3-dialkylether
US4814514A (en) * 1986-05-07 1989-03-21 Dai-Ichi Kogyo Seiyaku Co., Ltd. Surface active compounds having a polymerizable moiety

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4241224A (en) * 1979-10-09 1980-12-23 Basf Wyandotte Corporation Fiber lubricants derived from the oxyalkylation of a glycerol-1,3-dialkylether
US4814514A (en) * 1986-05-07 1989-03-21 Dai-Ichi Kogyo Seiyaku Co., Ltd. Surface active compounds having a polymerizable moiety

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0586323A1 (fr) * 1992-07-20 1994-03-09 Kao Corporation, S.A. Composition détergente et méthode pour sa fabrication
US5403509A (en) * 1992-07-20 1995-04-04 Kao Corporation, S.A. Detergent composition comprising a mono-, di- and tri-ester mixture and method of manufacturing same

Also Published As

Publication number Publication date
DE4021478A1 (de) 1992-01-09

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