EP0174610A2 - Utilisation d'éthersulfonates comme agents mouillants peu moussants dans des compositions de traitement technique aqueux, acide et alcalin - Google Patents

Utilisation d'éthersulfonates comme agents mouillants peu moussants dans des compositions de traitement technique aqueux, acide et alcalin Download PDF

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Publication number
EP0174610A2
EP0174610A2 EP85111229A EP85111229A EP0174610A2 EP 0174610 A2 EP0174610 A2 EP 0174610A2 EP 85111229 A EP85111229 A EP 85111229A EP 85111229 A EP85111229 A EP 85111229A EP 0174610 A2 EP0174610 A2 EP 0174610A2
Authority
EP
European Patent Office
Prior art keywords
alkaline
wetting agents
aqueous
ether sulfonates
agents
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.)
Granted
Application number
EP85111229A
Other languages
German (de)
English (en)
Other versions
EP0174610A3 (en
EP0174610B1 (fr
Inventor
Robert Dr. Piorr
Hildegard Van Delden
Sabine Lüttge
Bernd Bähr
Ingo Wegener
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
Priority to AT85111229T priority Critical patent/ATE42331T1/de
Publication of EP0174610A2 publication Critical patent/EP0174610A2/fr
Publication of EP0174610A3 publication Critical patent/EP0174610A3/de
Application granted granted Critical
Publication of EP0174610B1 publication Critical patent/EP0174610B1/fr
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/0026Low foaming or foam regulating compositions
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • CCHEMISTRY; METALLURGY
    • C23COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23GCLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G1/00Cleaning or pickling metallic material with solutions or molten salts
    • C23G1/14Cleaning or pickling metallic material with solutions or molten salts with alkaline solutions
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/10Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/03Organic sulfoxy compound containing

Definitions

  • aqueous treatment agents for the treatment of solid surfaces e.g. fibers, textiles, metals, ceramics or glass are strongly acidic or alkaline.
  • Technical treatment agents of this type e.g. Bleaches, mercerizing liquors, boiling, cleaning and degreasing agents, descaling, etching, pickling and rust removal agents require the addition of wetting agents in order to achieve faster and more intimate contact between the treatment agent and the solid surface.
  • wetting agents that are suitable for such acidic and alkaline, technical treatment agents must have good water solubility, even in acidic and alkaline medium, and must be largely stable against hydrolysis in these media. Since the technical treatment methods mentioned are often associated with strong mechanical movement, undesirable foaming easily occurs. Suitable wetting agents must therefore be very low-foaming. If this is not the case, the use of anti-foaming agents is necessary. However, the use of anti-foaming agents is not only associated with costs, but often has undesirable side effects, e.g. an uneven treatment of the surface or the formation of hydrophobic residues on the treated surface.
  • technical wetting agents should be environmentally friendly, that is, in particular, readily biodegradable and non-toxic to aquatic organisms.
  • wetting agents are characterized by very good water solubility, even in the presence of high concentrations of dissolved electrolytes, especially in the presence of acids and alkalis.
  • the invention therefore relates to the use of these ether sulfonates as wetting agents, especially in strongly acidic and strongly alkaline technical treatment solutions, especially in solutions which have a pH below 3 or above 10.
  • the ether sulfonates to be used according to the invention can be prepared by using an olefinically unsaturated fatty alkyl lower alkyl ether or an olefinically unsaturated fatty alkyl (polyoxyalkyl) lower alkyl ether of the general formula II in which R 1 , n and x have the abovementioned meaning and R 3 represents a mono- or di-unsaturated linear alkenyl group with 6-22 C atoms, reacted with sulfur trioxide, the reaction product in the aqueous solution of 1-1.2 moles of an alkali metal hydroxide per mole of S0 3 added and the solution formed until hydrolysis Sultons warmed up.
  • sultones are formed in addition to unsaturated ether sulfonic acids.
  • the ether sulfonates to be used according to the invention are therefore preferably mixtures of compounds of the formula I in which R 2 is alkenylene, hydroxyalkylene and hydroxyalkenylene groups.
  • the starting products of formula II are accessible by methods known from the literature. Their production is based on unsaturated alcohols of the formula R 3 -OH. If X is a number from 1-30, these are reacted according to the process known from the literature with X mol of an alkylene oxide of the formula C n H 2n o, for example with ethylene oxide or propylene oxide or mixtures of these alkylene oxides. Mixtures of homologous oxalkylates are obtained, the average degree of oxalkylation corresponding to the amount of alkylene oxide added. The etherification of the terminal hydroxyl group of the unsaturated alcohols and / or their oxalkylates is carried out by methods which are also known from the literature.
  • the alcohol or the oxalkylate is converted into the alcoholate with an alkali metal and this is converted with an alkyl halide, for example with an alkyl chloride of the formula R 1- Cl, is implemented.
  • Another method is to react the alcohol or the oxalkylate with an alkyl halide in the presence of a finely powdered alkali metal hydroxide at an elevated temperature.
  • the unsaturated alcohol R 3 -OH used is preferably an unsaturated fatty alcohol with 16-22 carbon atoms, ie an alcohol from the group palmitole alcohol, oleyl alcohol, linoleyl alcohol, eruca alcohol or a mixture of such alcohols, for example a technical fatty alcohol cut consisting predominantly of such alcohols .
  • Technical cetyl-oleyl and oleyl-linoleyl alcohol cuts with an iodine number in the range of 70-130 are preferably used,
  • Preferred wetting agents of the general formula I are obtained by addition of 3-10 mol of ethylene oxide onto these alcohols, etherification with alkyl halide, for example R 1 Cl, and sulfonation with SO 3 .
  • alkyl halide for example R 1 Cl
  • SO 3 sulfonation with SO 3 .
  • the wetting agents used according to the invention are distinguished by a particularly low foaming power. This is of particular advantage in strongly alkaline treatment agents, for example in alkaline cold bleaching liquors, hot bleaching liquors, mercerizing liquors, alkaline boiling and degreasing agents, since such alkaline treatment agents have a particular tendency to form foam.
  • the cause of the foam formation can either be the use of a foaming wetting agent or the formation of highly foaming hydrolysis products under the conditions of the surface treatment, for example the formation of soaps from hydrolyzed fats or of foaming protein breakdown products from protein compounds.
  • alkaline treatment agents are e.g. Mercerizing liquors, alkaline decoction solutions, alkaline degreasing agents and alkaline bleaching baths.
  • ether sulfonates as low-foaming wetting agents in aqueous alkaline bleaching liquors is particularly interesting. These contain hydrogen peroxide or compounds which form hydrogen peroxide in aqueous solution as a bleaching agent.
  • the pH of the bleaching baths is adjusted to 10-14 with strong bases, for example with NaOH, KOH, Na 2 CO 3 , K 2 CO 3 and / or water glass.
  • strong bases for example with NaOH, KOH, Na 2 CO 3 , K 2 CO 3 and / or water glass.
  • anionic and nonionic wetting agents which are stable and effective in this medium, tend to produce a lot of foam in the high-speed apparatus. For this reason, the use of foam damping agents, for example of the silicone oil type, is common.
  • a preferred object of the invention is therefore the use of the ether sulfonates of the general formula I in aqueous cold bleaching solutions containing 0.3-3% by weight of hydrogen peroxide, 0.05-1 mol / l of a strong base from the group of sodium hydroxide, potassium hydroxide and sodium carbonate , Potassium carbonate, sodium silicate and / or potassium silicate as low-foaming wetting agent, preferably in an amount of 0.05-1% by weight of the bleaching solution.
  • Such bleaching solutions are used at temperatures of 10-142 ° C, but preferably at a temperature of about 20 ° C (cold bleaching).
  • an ether sulfonate was prepared starting from the n-butyl ether of an adduct of 5 mol of ethylene oxide with a cetyl / oleyl alcohol of iodine number 52 (HD-Ocenol (R) 50/55).

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Textile Engineering (AREA)
  • Detergent Compositions (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
EP85111229A 1984-09-13 1985-09-05 Utilisation d'éthersulfonates comme agents mouillants peu moussants dans des compositions de traitement technique aqueux, acide et alcalin Expired EP0174610B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85111229T ATE42331T1 (de) 1984-09-13 1985-09-05 Verwendung von ethersulfonaten als schaumarme netzmittel in waessrigen, sauren und alkalischen technischen behandlungsmitteln.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3433593 1984-09-13
DE19843433593 DE3433593A1 (de) 1984-09-13 1984-09-13 Verwendung von ethersulfonaten als schaumarme netzmittel in waessrigen, sauren und alkalischen technischen behandlungsmitteln

Publications (3)

Publication Number Publication Date
EP0174610A2 true EP0174610A2 (fr) 1986-03-19
EP0174610A3 EP0174610A3 (en) 1987-05-27
EP0174610B1 EP0174610B1 (fr) 1989-04-19

Family

ID=6245287

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85111229A Expired EP0174610B1 (fr) 1984-09-13 1985-09-05 Utilisation d'éthersulfonates comme agents mouillants peu moussants dans des compositions de traitement technique aqueux, acide et alcalin

Country Status (4)

Country Link
US (1) US4612142A (fr)
EP (1) EP0174610B1 (fr)
AT (1) ATE42331T1 (fr)
DE (2) DE3433593A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991009987A1 (fr) * 1989-12-20 1991-07-11 Hughes Aircraft Company Composition de peroxyde pour l'elimination de contaminants organiques et sa methode d'utilisation
EP0447778A3 (en) * 1990-02-16 1991-12-04 Basf Aktiengesellschaft Vinyl polyether alcohols
EP0696661A1 (fr) * 1994-08-11 1996-02-14 Ciba-Geigy Ag Compositions d'agents de finition multi-fonctionnels
FR2736936A1 (fr) * 1995-07-19 1997-01-24 Air Liquide Procede de degraissage a base de peroxyde d'hydrogene et applications a des articles metalliques
DE19631150B4 (de) * 1996-08-01 2007-04-19 Süd-Chemie AG Verfahren zur Ablösung von Druckfarben (Deinking) von cellulosehaltigen Druckträgern

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4720492A (en) * 1981-01-19 1988-01-19 Petrolite Corporation Quaternary ammonium derivatives of 1,4-thiazine sulfonic acids
DE3435841A1 (de) * 1984-09-29 1986-04-17 Henkel KGaA, 4000 Düsseldorf Verwendung von ethersulfonaten als antistatika
DE3633421C1 (de) * 1986-10-01 1987-07-23 Goldschmidt Ag Th Hydroxyl- und Sulfonatgruppen aufweisende Polyoxyalkylenether und deren Verwendung zur Herstellung von dispergierbaren Polyurethanen
FI75918C (fi) * 1986-10-08 1988-08-08 Safematic Ltd Oy Glidringstaetning.
DE3725030A1 (de) * 1987-07-29 1989-02-09 Henkel Kgaa Oberflaechenaktive hydroxysulfonate
US5296627A (en) * 1988-06-20 1994-03-22 Ppg Industries, Inc. Ethylenically unsaturated poly(alkyleneoxy) surfactants
AU621916B2 (en) * 1988-06-20 1992-03-26 Ppg Industries, Inc. Polymerizable surfactant
US5075042A (en) * 1989-05-01 1991-12-24 Ppg Industries, Inc. Surfactant blend containing an alkyl poly(ethyleneoxy)sulfonate to reduce dermal irritation
US5196134A (en) * 1989-12-20 1993-03-23 Hughes Aircraft Company Peroxide composition for removing organic contaminants and method of using same
US5269850A (en) * 1989-12-20 1993-12-14 Hughes Aircraft Company Method of removing organic flux using peroxide composition
US5206286A (en) * 1990-04-02 1993-04-27 Ppg Industries, Inc. Aqueous emulsion polymers prepared with crosslinkable non-ionic surfactants
US5244960A (en) * 1990-04-02 1993-09-14 Ppg Industries, Inc. Thermosetting waterborne coating compositions prepared from aqueous emulsion polymers
US5138095A (en) * 1990-10-09 1992-08-11 Texaco Chemical Company Bisulfite addition products of ketone-terminated polyoxyalkylene compounds
US5110696A (en) * 1990-11-09 1992-05-05 Bell Communications Research Rechargeable lithiated thin film intercalation electrode battery

Family Cites Families (10)

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Publication number Priority date Publication date Assignee Title
US2062958A (en) * 1931-05-16 1936-12-01 Ether compounds
US3197333A (en) * 1960-08-30 1965-07-27 Berol Aktiebolag Processes of treating textile fibres before forming the same into a yarn
BE731492A (fr) * 1968-05-25 1969-09-15
US3592796A (en) * 1969-03-10 1971-07-13 Celanese Corp Linear polyester polymers containing alkali metal salts of sulfonated aliphatic compounds
US3639291A (en) * 1969-08-25 1972-02-01 Monsanto Co Surfactant composition and liquid detergent formulations containing same
BE792145A (fr) * 1971-12-02 1973-05-30 Bayer Ag Polymeres d'acrylonitrile ayant une resistance superficielle reduite etleur procede de preparation
CA1075453A (fr) * 1976-06-01 1980-04-15 Melvin E. Tuvell Methode d'extraction du petrole et agents surfactifs a base d'alkylalkoxypropiosulfonates
GB1566770A (en) * 1977-12-28 1980-05-08 Kuraray Co Etherification of polyocyalkylene compounds
JPS5950200B2 (ja) * 1978-02-17 1984-12-06 ライオン株式会社 改良された液体洗浄剤組成物
US4468335A (en) * 1981-04-30 1984-08-28 Mobil Oil Corporation Branched alkylpolyethoxypropane sulfonates and their use in enhanced oil recovery

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991009987A1 (fr) * 1989-12-20 1991-07-11 Hughes Aircraft Company Composition de peroxyde pour l'elimination de contaminants organiques et sa methode d'utilisation
EP0447778A3 (en) * 1990-02-16 1991-12-04 Basf Aktiengesellschaft Vinyl polyether alcohols
US5162590A (en) * 1990-02-16 1992-11-10 Basf Aktiengesellschaft Vinyl polyether alcohols
EP0696661A1 (fr) * 1994-08-11 1996-02-14 Ciba-Geigy Ag Compositions d'agents de finition multi-fonctionnels
FR2736936A1 (fr) * 1995-07-19 1997-01-24 Air Liquide Procede de degraissage a base de peroxyde d'hydrogene et applications a des articles metalliques
EP0756023A1 (fr) * 1995-07-19 1997-01-29 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Procédé de dégraissage à base de peroxyde d'hydrogène et applications à des articles métalliques
DE19631150B4 (de) * 1996-08-01 2007-04-19 Süd-Chemie AG Verfahren zur Ablösung von Druckfarben (Deinking) von cellulosehaltigen Druckträgern

Also Published As

Publication number Publication date
EP0174610A3 (en) 1987-05-27
US4612142A (en) 1986-09-16
DE3569569D1 (en) 1989-05-24
ATE42331T1 (de) 1989-05-15
DE3433593A1 (de) 1986-03-20
EP0174610B1 (fr) 1989-04-19

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