EP0007049B1 - Detergenzzusammensetzung - Google Patents

Detergenzzusammensetzung Download PDF

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Publication number
EP0007049B1
EP0007049B1 EP79102205A EP79102205A EP0007049B1 EP 0007049 B1 EP0007049 B1 EP 0007049B1 EP 79102205 A EP79102205 A EP 79102205A EP 79102205 A EP79102205 A EP 79102205A EP 0007049 B1 EP0007049 B1 EP 0007049B1
Authority
EP
European Patent Office
Prior art keywords
weight
formula
ethylene oxide
mixture
acid
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.)
Expired
Application number
EP79102205A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0007049A1 (de
Inventor
Ingo Wegener
Johann Dr. Glasl
Achim Dr. Werdehausen
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 EP0007049A1 publication Critical patent/EP0007049A1/de
Application granted granted Critical
Publication of EP0007049B1 publication Critical patent/EP0007049B1/de
Expired 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
    • C11D1/66—Non-ionic compounds
    • C11D1/825—Mixtures of compounds all of which are non-ionic
    • 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
    • C11D1/825—Mixtures of compounds all of which are non-ionic
    • C11D1/8255—Mixtures of compounds all of which are non-ionic containing a combination of compounds differently alcoxylised or with differently alkylated chains
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents

Definitions

  • the invention relates to detergent compositions based on nonionic surfactants which have a reduced viscosity at room temperature.
  • detergent compositions based on adducts of ethylene oxide with fatty alcohols which, like the known mixtures with anionic surfactants, have a reduced viscosity at room temperature, but do not have the disadvantages of the latter.
  • the new compositions contain adducts of ethylene oxide with internal vicinal alkanediols.
  • the invention accordingly relates to a detergent composition which is characterized by a content of 40 to 60% by weight of compounds of the formula I, in which R 1 is a saturated or unsaturated hydrocarbon radical of a fatty alcohol having 6 to 18 carbon atoms and n is a number from 4 to 15, and a content of 60 to 40% by weight of compounds of the formula 11, in which R 2 and R 3 are alkyl radicals having 1 to 17 carbon atoms, the sum of the carbon atoms in R 2 and R 3 being 8 to 18, p and q representing numbers from 0 to 15 and the sum p + q in the range from 4 up to 15.
  • the compounds of formula 1 are known substances which can be obtained by known processes.
  • Saturated and unsaturated fatty alcohols with 6 to 18 carbon atoms such as n-hexanol, n-octanol, n-decanol, n-dodecanol, n-tetradecanol, n-hexadecanol, n-octadecanol and 9-octadecenol (1 ) are used.
  • fatty alcohol mixtures are used to synthesize these surface-active substances, as are obtained in the sodium reduction or the catalytic hydrogenation of fatty acid mixtures from the hydrolytic cleavage of native fats and oils.
  • the compounds of formula 11 are also known substances. They can be obtained by known processes by adding the appropriate amount of ethylene oxide to alkanediols with non-terminal, vicinal hydroxyl groups and 10 to 20 carbon atoms. Mixtures of alkane diols with different chain lengths and / or isomeric positions of the hydroxyl groups are preferably used for the preparation of the compounds of formula 11. Such alkanediols can be obtained in a known manner from olefins and olefin mixtures with internal double bonds which are randomly distributed over the hydrocarbon chain by epoxidation and subsequent hydrolysis of the resulting epoxyalkanes.
  • Corresponding olefins and olefin mixtures are e.g. accessible by catalytic dehydrogenation or chlorination-dehydrochlorination of linear paraffins of the chain length range of interest and subsequent selective extraction of the monoolefins with non-terminal double bonds.
  • These olefins are made by known methods, e.g. with peracetic acid, epoxidized.
  • the hydrolysis of the epoxyalkanes is also carried out by processes known from the literature, the procedure described in DE-OS 22 56 907 having proven particularly advantageous. According to this process, the epoxyalkanes are hydrolyzed with 1 to 20% by weight aqueous solutions of salts of aliphatic mono- and / or polycarboxylic acids at temperatures above 100 ° C. and up to 300 ° C.
  • alkali metal salts especially the sodium salts of acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid and pelargonic acid.
  • Salts of dicarboxylic acids such as malonic acid, succinic acid, adipic acid, maleic acid, fumaric acid, azelaic acid and sebacic acid are preferred. Mixtures of salts of mono- and dicarboxylic acids can also be used.
  • the quantitative ratio between the epoxy to be hydrolyzed and the salt solution should be at least 0.5 part by weight of salt solution per part by weight of epoxy; in general, it has proven advantageous to use 2 to 5 parts by weight of saline per part by weight of epoxy.
  • solubilizers such as acetone, dioxane and dioxolane.
  • the solubilizers are used in amounts of at least 0.5 part by weight per part by weight of epoxy to be hydrolyzed. A weight ratio of 2: 1 is particularly favorable.
  • the reaction can be carried out in such a way that the mixture of epoxy, salt solution and optionally solubilizer is heated to the relevant reaction temperature while stirring in an autoclave and is kept at this temperature until the hydrolysis is complete. In general, reaction times of 15 minutes to 2 hours are sufficient here.
  • reaction mixtures can be worked up in a simple manner after separation by distillation of any solvent which may be present by phase separation in the heat.
  • Suitable starting materials for the preparation of compounds of the formula 11 are, for example, a mixture of isomeric vicinal alkane diols of chain length C 10 with non-terminal hydroxyl groups, a mixture of isomeric vicinal alkane diols of chain length C 18 with non-terminal hydroxyl groups, a mixture of isomeric vicinal alkane diols Chain length C 11 -C 15 with non-terminal hydroxyl groups, a mixture of isomeric vicinal alkane diols of chain length C 14 _C 16 with non-terminal hydroxyl groups and a mixture of vicinal alkane diols of chain length C 15 _C 18 with non-terminal hydroxyl groups.
  • the alkane diol mixtures described above are reacted with the appropriate amount of ethylene oxide at elevated temperature and pressure in the presence of suitable alkoxylation catalysts.
  • the substances obtained are usually semi-solid to solid, wax-like products.
  • Another route to the compounds of the formula II is via the reaction of the epoxyalkanes described above with ethylene glycol and the subsequent ethoxylation of the 2-hydroxyethyl-2-hydroxyalkyl ether obtained.
  • the epoxides obtained from olefin mixtures are reacted in a known manner in the presence of acidic alkoxylation catalysts at elevated temperature and, if appropriate, at elevated pressure with ethylene glycol present in excess.
  • this reaction is carried out in the presence of a saturated aliphatic hydrocarbon, e.g. Pentane, hexane, heptane and octane.
  • reaction products obtained are reacted at elevated temperature and pressure in the presence of suitable alkoxylation catalysts with the intended amount of ethylene oxide to give the compounds of the formula II.
  • suitable alkoxylation catalysts with the intended amount of ethylene oxide to give the compounds of the formula II.
  • the products manufactured in this way are also semi-solid to solid, waxy products.
  • detergent compositions with a particularly favorable characteristic in terms of application technology are obtained if the compounds of formula I and formula 11 used for their preparation have approximately the same hydrophilicity. Accordingly, detergent compositions in which the difference between n in formula I and the sum p + q in formula II ⁇ 2 is a specific embodiment of the invention.
  • the compounds of the formulas I and II are mixed with one another in the desired ratio by means of an agitator or kneader.
  • Example 2 60 parts by weight of an adduct of 5 mol of ethylene oxide with a tallow fatty alcohol mixture of chain length C 14 _C 18 (OH number 216) were mixed as in Example 1 with 40 parts by weight of a product which was obtained by reaction of an epoxyalkane mixture of chain length C 15 C, 18 with non-terminal epoxy groups (5.35 wt .-% epoxy oxygen) with ethylene glycol and subsequent addition of 5 moles of ethylene oxide was obtained.
  • the resulting detergent mixture was liquid, but slightly cloudy; it easily dissolved in water without difficulty.
  • Example 1 50 parts by weight of an adduct of 12 moles of ethylene oxide with an oleyl-cetyl alcohol mixture (OH number 216; iodine number 65) were mixed as in Example 1 with 50 parts by weight of a product which was obtained by reaction of an epoxyalkane mixture of chain length C 16 _C 18 with non-terminal epoxy groups (5.75% by weight epoxy oxygen) with ethylene glycol and subsequent addition of 10 moles of ethylene oxide had been obtained.
  • a liquid product was obtained which spontaneously dissolved in water without annoying gel formation.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
EP79102205A 1978-07-06 1979-07-02 Detergenzzusammensetzung Expired EP0007049B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2829697 1978-07-06
DE2829697A DE2829697C2 (de) 1978-07-06 1978-07-06 Detergenzzusammensetzung

Publications (2)

Publication Number Publication Date
EP0007049A1 EP0007049A1 (de) 1980-01-23
EP0007049B1 true EP0007049B1 (de) 1981-04-29

Family

ID=6043696

Family Applications (1)

Application Number Title Priority Date Filing Date
EP79102205A Expired EP0007049B1 (de) 1978-07-06 1979-07-02 Detergenzzusammensetzung

Country Status (4)

Country Link
US (1) US4234444A (enrdf_load_stackoverflow)
EP (1) EP0007049B1 (enrdf_load_stackoverflow)
JP (1) JPS5512194A (enrdf_load_stackoverflow)
DE (1) DE2829697C2 (enrdf_load_stackoverflow)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2948100A1 (de) * 1979-11-29 1981-06-11 Henkel KGaA, 4000 Düsseldorf Detergenzzusammensetzung
GB8409867D0 (en) * 1984-04-16 1993-06-16 Ici Plc Nitrocellulose propellant composition
US4753750A (en) * 1984-12-31 1988-06-28 Delaware Liquid laundry detergent composition and method of use
JPS61166894A (ja) * 1985-01-18 1986-07-28 ライオン株式会社 界面活性剤
DE3713962A1 (de) * 1987-04-25 1988-11-10 Henkel Kgaa Waeschevorbehandlungsmittel fuer oel- und fettanschmutzungen
DE3730179A1 (de) * 1987-09-09 1989-03-23 Henkel Kgaa Verdickte waessrige tensidloesungen, insbesondere fuer deren einsatz auf dem gebiet kosmetischer praeparate
US4919834A (en) * 1988-09-28 1990-04-24 The Clorox Company Package for controlling the stability of a liquid nonaqueous detergent
US4874537A (en) * 1988-09-28 1989-10-17 The Clorox Company Stable liquid nonaqueous detergent compositions
DE4006391A1 (de) * 1990-03-01 1991-09-05 Henkel Kgaa Giessbares, fluessiges tensidkonzentrat
DE4421270A1 (de) * 1994-06-20 1995-12-21 Henkel Kgaa Wäßrige Fettalkoholdispersionen
US6204297B1 (en) * 1996-11-26 2001-03-20 Rhodia Inc. Nonionic gemini surfactants
US20050203187A1 (en) * 1998-06-01 2005-09-15 Verbiscar Anthony J. Formulations useful for the treatment of varicella zoster virus infections and methods for the use thereof
DE10154103A1 (de) 2001-11-02 2003-05-15 Cognis Deutschland Gmbh Biologisch abbaubare Zusammensetzungen
US6918222B2 (en) * 2003-09-09 2005-07-19 Illinois Tool Works Inc. Fastener for spacing object from substrate
DE102004056853A1 (de) * 2004-11-25 2006-06-01 Cognis Deutschland Gmbh & Co. Kg Verwendung von Fettalkoholpolyglykolethersulfaten für die Emulsionspolymerisation
US20090258983A1 (en) * 2006-10-20 2009-10-15 Cognis Ip Management Gmbh Surfactant Compositions and Methods of Forming and Using Same
JP5522680B2 (ja) * 2010-05-11 2014-06-18 ミヨシ油脂株式会社 ノニオン型界面活性剤
CN115667194A (zh) 2020-11-30 2023-01-31 花王株式会社 化合物，其前体化合物，表面活性剂组合物以及清洗剂组合物

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3882038A (en) * 1968-06-07 1975-05-06 Union Carbide Corp Cleaner compositions
US3707506A (en) * 1968-08-19 1972-12-26 Basf Wyandotte Corp Nonionic detergent compositions for cleaning polyester fabrics
US3682849A (en) * 1970-10-08 1972-08-08 Shell Oil Co Alcohol ethoxylates
DE2256907C3 (de) * 1972-11-20 1982-03-18 Henkel KGaA, 4000 Düsseldorf Verfahren zur Herstellung von vicinalen Di- und Polyolen
IT1006662B (it) * 1972-12-04 1976-10-20 Monsanto Co Composizioni tensioattive
DE2318950C2 (de) * 1973-04-14 1982-03-11 Degussa Ag, 6000 Frankfurt Verbessertes Verfahren zur Herstellung von Hydroxyalkylglykoläthern
DE2331014C2 (de) * 1973-06-18 1982-06-24 Henkel KGaA, 4000 Düsseldorf Äthoxylierungsprodukte, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung in Wasch- und Reinigungsmitteln
DE2327860A1 (de) * 1973-06-01 1975-01-02 Henkel & Cie Gmbh Phosphatfreies waschmittel

Also Published As

Publication number Publication date
DE2829697A1 (de) 1980-01-17
JPS5512194A (en) 1980-01-28
EP0007049A1 (de) 1980-01-23
JPS6314036B2 (enrdf_load_stackoverflow) 1988-03-29
DE2829697C2 (de) 1986-10-30
US4234444A (en) 1980-11-18

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