EP0453447B1 - Utilisation des esters polyoxyalkyliques d'acides monocarboxyliques sulfones en tant que produits d'entretien textile peu moussants - Google Patents

Utilisation des esters polyoxyalkyliques d'acides monocarboxyliques sulfones en tant que produits d'entretien textile peu moussants Download PDF

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Publication number
EP0453447B1
EP0453447B1 EP90900177A EP90900177A EP0453447B1 EP 0453447 B1 EP0453447 B1 EP 0453447B1 EP 90900177 A EP90900177 A EP 90900177A EP 90900177 A EP90900177 A EP 90900177A EP 0453447 B1 EP0453447 B1 EP 0453447B1
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Prior art keywords
monocarboxylic acid
acid
low
acid polyoxyalkyl
salts
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EP90900177A
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German (de)
English (en)
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EP0453447A1 (fr
Inventor
Ansgar Behler
Bernd Fabry
Bernd Wahle
Hildegard Von Delden
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Priority to AT90900177T priority Critical patent/ATE86292T1/de
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/38—Oxides or hydroxides of elements of Groups 1 or 11 of the Periodic Table
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0026—Low foaming or foam regulating compositions
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
    • D06L4/12—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen combined with specific additives

Definitions

  • the invention relates to the use of monocarboxylic acid polyoxyalkyl ester sulfonates as low-foaming wetting agents in aqueous alkaline pretreatment agents for textile fabrics.
  • wetting agents that are suitable for such alkaline treatment agents must be water-soluble and alkali-stable, and must ensure uniform wetting of the goods.
  • wetting agents should be environmentally friendly, i.e. biodegradable and have no toxic effects on aquatic organisms.
  • defoamers for example silicones
  • the use of defoamers is not only with additional ones Costs associated, but often has undesirable side effects, for example an uneven wetting of the textile fabrics, as well as silicone oil stains that are difficult to remove in the case of silicone-containing defoamers.
  • the object of the invention was therefore to develop silicone-free, low-foaming, liquid and thus directly meterable, water-soluble, alkali-stable and readily biodegradable wetting agents for textile fabrics or yarns, which meet all of these product requirements in a uniform substance.
  • the invention is based on the surprising finding that the high requirements placed on wetting agents of monocarboxylic acid polyoxyalkyl ester sulfonic acids in the form of their alkali metal, ammonium and / or amine salts are met.
  • the invention accordingly relates to the use of alkali metal, ammonium and / or amine salts of carboxylic acid polyoxyalkyl ester sulfonic acids, prepared by reacting monounsaturated monocarboxylic acid polyoxyalkyl esters of the general formula in which R is an alkyl radical with 1 to 22 C atoms or an alkenyl radical with 3 to 22 C atoms, m is a number from 10 to 21, n is 2 and / or 3 and x is a number from 1 to 20, with Sulfur trioxide and subsequent reaction of the sulfonated monocarboxylic acid polyoxyalkyl esters obtained with aqueous alkalis as low-foaming wetting agents in aqueous alkaline pretreatment agents for textile fabrics or yarns.
  • R is an alkyl radical with 1 to 22 C atoms or an alkenyl radical with 3 to 22 C atoms
  • m is a number from 10 to 21
  • n is 2 and /
  • the salts of monocarboxylic acid polyoxyalkylester sulfonic acids can be prepared in a manner known per se, in which monounsaturated monocarboxylic acid polyoxyalkyl esters are sulfonated at temperatures between 5 and 120 ° C. with sulfuric acid, oleum, chlorosulfonic acid or SO3-containing gas mixtures.
  • the sulfonation temperatures are particularly preferably between 5 and 40 ° C.
  • the molar ratio of monounsaturated monocarboxylic acid polyoxyalkyl: SO3 is about 1: 1.
  • the sulfonations are carried out continuously or batchwise in conventional reactors suitable and customary for the sulfation of fatty alcohols or for the sulfonation of fatty acid esters, alkylbenzenes or olefins, preferably of the type of falling film reactor (see, for example, in Kirk-Othmer: Encyclopedia of Chemical Technologie 22 , 28 ff (1983)).
  • the sulfonation product obtained is then hydrolyzed with an aqueous solution of alkali metal hydroxides, ammonium hydroxide and / or amines, in which the sulfonated reaction mixture is preferably added to the aqueous solution.
  • 1 to 1.2 moles of hydroxides and / or amines are used per mole of sulfur trioxide added.
  • Excess hydroxide and / or amine is required to neutralize the gaseous SO3 dissolved in the sulfonation product.
  • Sodium hydroxide, potassium hydroxide, diethanolamine and / or triethanolamine, particularly preferably sodium hydroxide, are preferably used as neutralization bases.
  • the concentration of the hydroxides and / or amines in water is preferably chosen so that the end product forms a low-viscosity solution.
  • the reaction product also contains sultones.
  • the formation of sultons is a known reaction in the sulfonation of olefinic double bonds.
  • hydrolysis in which the reaction products are heated until the sultone groups formed have been completely destroyed while maintaining a pH of 7 by controlled addition of alkali metal hydroxide will.
  • the time required for this is dependent on pressure and temperature. For example, a complete hydrolysis can be achieved in 4 to 6 hours at boiling temperature under normal pressure, under pressure at higher temperatures, but in a considerably shorter time.
  • the monounsaturated monocarboxylic acid polyoxyalkyl esters of the general formula to be used as starting materials are also accessible using methods known from the literature. They are produced from aliphatic, natural and / or synthetic, saturated alcohols with 1 to 22 carbon atoms and / or aliphatic, natural and / or synthetic, unsaturated alcohols with 3 to 22 carbon atoms, for example methanol, ethanol, propanol, butanol, hexanol, Octanol, decanol, cetyl alcohol, stearyl alcohol, behenyl alcohol, oleyl alcohol, palmitoleyl alcohol, linoleyl alcohol, eruca alcohol or technical alcohol cuts consisting predominantly of cetyl alcohol, stearyl alcohol, oleyl alcohol, palmitoleyl alcohol and / or linoleyl alcohol.
  • the alkoxylations of the alcohols with ethylene oxide and / or propylene oxide are carried out using known industrial processes carried out (see, for example, in Chemische Technologie, Volume 7, pages 131 to 132, Carl-Hanser-Verlag, Kunststoff (1986)).
  • the average degree of oxalkylation x of the mixtures of homologous oxalkylates obtained corresponds to the molar amount of the alkylene oxides attached and is between 1 and 20, preferably between 2 and 10.
  • oxyalkylated alcohols obtained are then reacted with C11 ⁇ 22 monounsaturated monocarboxylic acids in a manner known per se in the presence of esterification catalysts, for example tin grinding.
  • Suitable monounsaturated monocarboxylic acids with 11 to 22 carbon atoms are, for example, 10-undecenoic acid, palmitoleic acid, oleic acid, petroselinic acid, elaidic acid and / or erucic acid.
  • oleic acid and / or erucic acid are used in pure form or in the form of fatty acid mixtures rich in oleic acid and erucic acid, as can be obtained from fats of animal and / or vegetable origin.
  • Preferred monounsaturated monocarboxylic acid polyoxyalkyl esters are those of the general formula used, in which R represents an alkyl radical having 8 to 18 carbon atoms, m 17 and / or 21, n 2 and / or 3 and x is a number between 2 to 10.
  • the wetting agents to be used according to the invention are light yellow to light brown, clear, aqueous, alkaline solutions. If desired, these can be bleached with hydrogen peroxide solutions or alkali hypochlorite solutions (chlorine solution) in a manner known per se at temperatures between 40 and 55 ° C. For stabilization against bacterial contamination, preservation with preservatives known from the prior art, for example p-hydroxybenzoate and / or sorbic acid, is recommended.
  • the active substance content of monocarboxylic acid polyoxyalkyl ester sulfonate salts in the solutions is between 10 and 50% by weight.
  • Monocarboxylic acid polyoxyalkyl ester sulfonate salt-containing wetting agents are distinguished by a particularly low foaming power. This is of particular advantage in strongly alkaline pretreatment agents, for example in alkaline cold bleaching liquors, hot bleaching liquors, mercerizing liquors, alkaline decoction and degreasing agents, since such alkaline pretreatment agents have a particular tendency to form foam.
  • the monocarboxylic acid polyoxyalkyl ester sulfonate salts are preferably used as low-foaming wetting agents in aqueous alkaline bleaching liquors. 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 to 14 with strong bases, for example with NaOH and / or KOH.
  • the known anionic and nonionic wetting agents for example alkyl sulfates, sulfonates, carboxylates, phosphates and / or alkylpolyoxyethylene glycol ethers, which are stable and effective in these media, tend to produce a lot of foam in the high-speed apparatus.
  • foam damping agents for example silicone oils
  • the salts of monocarboxylic acid polyoxyalkyl ester sulfonic acids to be used according to the invention develop practically no foam in such baths, so that the addition of defoamers is unnecessary.
  • the bleaching liquors containing 10 to 100 ml of hydrogen peroxide, 35% by weight, 5 to 20 g of bases from the group of sodium or / or potassium hydroxide, 5 to 50 ml of stabilizers, for example sodium water glass (Na2O: SiO2 1: 2 ; 38 - 40 ° Bé) and / or alkali salts of ethylenediaminetetraacetic acid and / or polyphosphates, 0.1 to 1.0 g of magnesium salts, for example magnesium sulfate, 0.5 to 10 g of sequestering agent, for example Securon R 540, Henkel KGaA and 0.3 to 30 g, based on active substance, of monocarboxylic acid polyoxyalkyl ester sulfonate salts, are used at temperatures between 15 and 90 ° C, preferably at a temperature of about 20 ° C (cold bleach), on textile fabrics or yarns.
  • stabilizers for example sodium water glass (Na2O: Si
  • the cotton-containing textile fabrics such as woven and / or knitted fabrics, which are preferably treated with bleaching liquors containing monocarboxylic acid polyoxyalkyl sulfonate salt, and yarns are distinguished by good degrees of whiteness and good hydrophilic properties.
  • the bleaching liquors were treated with oleic acid 2.9EO decyl ester sodium sulfonate, prepared according to Example 1.1, and for comparison oleic acid oleyl ester sodium sulfonate, prepared according to example 1.2, or oleic acid 2.9EO decyl ester as wetting agent in different Amounts added.
  • the wetting effect of these liquors was determined at 20 ° C. in accordance with DIN 53 901 (determination of the immersion wetting power of surfactant solutions). The following network times were obtained:
  • the foaming behavior of the cold bleaching solutions (composition analogous to 2.b)), the wetting agent 2.4 g AS / l cold bleaching liquor oleic acid 2.9EO decyl ester sodium sulfonate and for comparison 2.4 g AS / l cold bleaching liquor oleic acid oleylester sodium sulfonate or 2.4 g AS / l cold bleaching liquor containing oleic acid 2.9EO decyl ester was checked at 20 ° C on the Krantz dyeing machine (capacity: 25 l, liquor run-in from the outside in, running time: 15 minutes) (0% means none Foam between the liquid surface and the edge of the container, 100% means that the volume between the liquid surface and the edge of the container is completely filled with foam).

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (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)

Abstract

Utilisation de sels alcalins, d'ammonium et/ou d'amine d'acides sulfoniques de polyalkylester d'acide monocarboxylique en tant qu'agents mouillants peu moussants dans des produits d'entretien alcalins aqueux pour non-tissés ou fils textiles.

Claims (4)

  1. Utilisation de sels de métaux alcalins, d'ammonium et/ou d'amines d'esters polyoxyalkyliques d'acides monocarboxyliques sulfonés, que l'on prépare en faisant réagir des esters polyoxyalkyliques d'acides monocarboxyliques une fois insaturés répondant à la formule générale
    Figure imgb0011
     dans laquelle R représente un radical alkyle contenant de 1 à 22 atomes de carbone ou un radical alcényle contenant de 3 à 22 atomes de carbone, m représente un nombre entre 10 et 21, n est égal à 2 et/ou 3 et x représente un nombre entre 1 et 20, avec du trioxyde de soufre, et par réaction ultérieure de l'ester polyoxyalkylique d'acide monocarboxylique sulfoné obtenu, avec des alcalis aqueux, à titre d'agents mouillants pauvres en mousse dans des agents de prétraitement alcalins aqueux destinés à des produits textiles de forme plane ou à des fils.
  2. Utilisation selon la revendication 1, caractérisée en ce que R représente un radical allyle contenant de 8 à 18 atomes de carbone, m est égal à 17 et/ou 21, n est égal à 2 et/ou 3 et x représente un nombre entre 2 et 10.
  3. Utilisation selon une des revendication 1 et 2 ou selon les deux, caractérisée en ce qu'on utilise des sels sulfonates d'esters polyoxyalkyliques d'acides monocarboxyliques dans des agents alcalins aqueux de prétraitement pour des produits textiles de forme plane contenant du coton ou pour des fils contenant du coton.
  4. Utilisation selon une ou plusieurs des revendications 1 à 3, caractérisée en ce que les agents de prétraitement sont des agents alcalins de blanchiment qui contiennent, par litre, de 10 à 100 ml de peroxyde d'hydrogène à raison de 35%, de 5 à 20 g de bases, de 5 à 50 ml de stabilisants, de 0,1 à 1,0 g de sels de magnésium, de 0,5 à 10 g d'agents séquestrants et de 0,3 à 30 g, rapportés à la substance active, de sels de métaux alcalins, d'ammonium et/ou d'amines d'esters polyoxyalkyliques d'acides monocarboxyliques sulfonés.
EP90900177A 1989-01-12 1990-01-04 Utilisation des esters polyoxyalkyliques d'acides monocarboxyliques sulfones en tant que produits d'entretien textile peu moussants Expired - Lifetime EP0453447B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT90900177T ATE86292T1 (de) 1989-01-12 1990-01-04 Verwendung von monocarbonsaeurepolyoxyalkylester - sulfonaten als schaumarme textilbehandlungsmittel.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3900699A DE3900699A1 (de) 1989-01-12 1989-01-12 Verwendung von monocarbonsaeurepolyoxyalkylester-sulfonaten als schaumarme netzmittel in waessrigen alkalischen behandlungsmitteln fuer textile flaechengebilde
DE3900699 1989-01-12

Publications (2)

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EP0453447A1 EP0453447A1 (fr) 1991-10-30
EP0453447B1 true EP0453447B1 (fr) 1993-03-03

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US (1) US5250076A (fr)
EP (1) EP0453447B1 (fr)
JP (1) JPH04502651A (fr)
BR (1) BR9007019A (fr)
DE (2) DE3900699A1 (fr)
ES (1) ES2054330T3 (fr)
WO (1) WO1990008181A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4039348A1 (de) * 1990-12-10 1992-06-11 Henkel Kgaa Teppichreinigungsmittel
WO1993025646A1 (fr) * 1992-06-17 1993-12-23 Lion Corporation Composition detergente peu agressive pour la peau
US5417708A (en) * 1994-03-09 1995-05-23 Cook Incorporated Intravascular treatment system and percutaneous release mechanism therefor
US5968370A (en) * 1998-01-14 1999-10-19 Prowler Environmental Technology, Inc. Method of removing hydrocarbons from contaminated sludge
PL442737A1 (pl) 2022-11-04 2024-05-06 Pcc Rokita Spółka Akcyjna Sposób selektywnego otrzymywania paradichlorobenzenu z ulepszonym odzyskiem układu katalitycznego

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2243306A1 (de) * 1972-09-02 1974-03-21 Henkel & Cie Gmbh Schaumregulierte waschmittel, insbesondere fuer trommelwaschmaschinen
CH610209A5 (en) * 1976-04-26 1979-04-12 Ciba Geigy Ag Wetting agent and foam inhibitor based on anionic surfactants
BE1000328A5 (fr) * 1987-02-19 1988-10-25 Interox Sa Particules de composes peroxygenes stabilisees, procede pour leur fabrication, et compositions en contenant.
US4963157A (en) * 1987-04-17 1990-10-16 Nippon Peroxide Co., Ltd. Method for bleaching cellulosic fiber material with hydrogen peroxide
DE3720000A1 (de) * 1987-06-15 1988-12-29 Henkel Kgaa Fettsaeurepolyoxyalkylester-sulfonate, verfahren zu ihrer herstellung und ihre verwendung als tenside

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Chemical Abstracts, Vol. 92, Nr. 18, 5 May 1980 Columbus, Ohio, USA:Skripchemko, E.S. & al.:"Antifrothing agent" page 124; ref. No. 148922 *

Also Published As

Publication number Publication date
WO1990008181A1 (fr) 1990-07-26
ES2054330T3 (es) 1994-08-01
EP0453447A1 (fr) 1991-10-30
US5250076A (en) 1993-10-05
JPH04502651A (ja) 1992-05-14
DE59000985D1 (de) 1993-04-08
BR9007019A (pt) 1991-11-12
DE3900699A1 (de) 1990-07-19

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