EP0302402A2 - Agents de lavage et de nettoyage pour le linge - Google Patents

Agents de lavage et de nettoyage pour le linge Download PDF

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Publication number
EP0302402A2
EP0302402A2 EP88112291A EP88112291A EP0302402A2 EP 0302402 A2 EP0302402 A2 EP 0302402A2 EP 88112291 A EP88112291 A EP 88112291A EP 88112291 A EP88112291 A EP 88112291A EP 0302402 A2 EP0302402 A2 EP 0302402A2
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EP
European Patent Office
Prior art keywords
sodium
detergent
weight
embodiment according
washing
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.)
Withdrawn
Application number
EP88112291A
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German (de)
English (en)
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EP0302402A3 (fr
Inventor
Alfred Dr. Meffert
Andreas Dr. Syldatk
Brigitte Giesen
Ingo Wegener
Johann-Friedrich Dr. Fues
Peter Dr. Gerike
Peter Dr. Gode
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Publication of EP0302402A2 publication Critical patent/EP0302402A2/fr
Publication of EP0302402A3 publication Critical patent/EP0302402A3/fr
Withdrawn legal-status Critical Current

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    • 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
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3942—Inorganic per-compounds
    • 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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/06—Phosphates, including polyphosphates
    • 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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/12—Water-insoluble compounds
    • C11D3/124—Silicon containing, e.g. silica, silex, quartz or glass beads
    • C11D3/1246—Silicates, e.g. diatomaceous earth
    • C11D3/128—Aluminium silicates, e.g. zeolites

Definitions

  • the invention relates to a further development of textile washing and cleaning agents which contain detergent surfactants in a mixture with builder substances for their use in washing or cleaning textiles in an aqueous liquor.
  • the invention is based in particular on the object of further improving the environmental compatibility of the active substance mixtures required for textile washing and cleaning.
  • the invention is based on the object of further facilitating the disposal of used washing and cleaning solutions in that wash-active surfactant systems are to be used which are characterized by optimal environmental compatibility and in particular by optimal values for acute aquatic toxicity, so that undesired side effects in the destruction of used washing and cleaning liquors are suppressed as far as possible.
  • the invention seeks to maintain as much as possible the high cleaning power of today's branded laundry detergents in the field of textile washing.
  • the teaching of the invention is based on the finding that the di-salts of alpha-sulfonated fatty acids of natural and / or synthetic origin, in particular the chain length range of C10 ⁇ 22, preferably the C number range of C14 ⁇ 18 and very particularly the corresponding sodium -Disalts of the tallow fatty acid range (C 16/18 ) are characterized by optimal properties in their ecological assessment.
  • ABS or LAS shows an LC value of 3.2 to 4.9 mg / l when determining the acute aquatic toxicity on fish (gold thrown, 48 h). The corresponding value of daphnia (24 hours) is 8.9 to 14 mg / l.
  • Comparable LC50 values for alcohol ethoxylates are in the range of 1 to 50 mg / l for fish and in the range of 2 to 200 mg / l for daphnia.
  • sodium disalts of alpha-sulfo fatty acids - hereinafter referred to simply as "sodium disalts" - shows their considerable weakness as a detergent active, determined as the primary detergency on standard soiled test fabrics in conventional detergent mixtures. Although it has always been known that sodium disalts of the type in question can have a certain washing power, they have been regarded as unusable for practical use as a surfactant component or even as a main surfactant component.
  • DE-ASen 21 44 592 and 21 61 726 describe textile detergents which, in addition to the usual washing-active nonionic and / or anionic surfactant components, contain alkali metal salts of alpha-sulfonated saturated fatty acids with 14 to 20 carbon atoms. These sodium disalts should either serve alone as builders for the surfactant components used or together with conventional builders combinations, in particular based on calcium ions complex binding and / or precipitating builders salts are used. A further modification of this application of the sodium disalts as builder components is described in the European patents 00 70 190 and 00 70 191 (in each case B1).
  • the sodium disalts of alpha-sulfonated carboxylic acids are to be used here as cobuilders together with sodium zeolite as the main builder component in textile detergent mixtures based on customary surfactant mixtures. All these proposals have nothing in common with the object of the invention to design sodium disalts of the type mentioned because of their ecological properties, which are unique in the relevant surfactant sector, into a functionally essential or even the only detergent-active surfactant component in the context of textile detergents.
  • JA-OS 60-18592 describes a bleaching detergent mixture which is characterized by the content of (A) 1-15% by weight of an alkali metal salt of sulfofatty acids of the type concerned here and (B) 3-15% by weight Sodium percarbonate.
  • A 1-15% by weight of an alkali metal salt of sulfofatty acids of the type concerned here
  • B 3-15% by weight Sodium percarbonate.
  • ABS or LAS is mentioned first as a suitable surface-active surfactant.
  • JA-OS 58-125849 describes a textile detergent with a finishing effect which, in addition to 5-30% by weight of an anionic surface-active agent (A), contains 0.1-10% by weight of a quaternary ammonium compound (B).
  • Alkaline or alkaline earth metal salts of alpha-sulfofatty acids and / or corresponding esters of alpha-sulfofatty acid should predominantly be used as surfactant component A.
  • the invention is based on the surprising finding that it adheres to a plurality of parameters in the The composition of the detergent concentrates, on the one hand, and the desired dosage of detergent compositions composed according to the invention in the wash liquor, on the other hand, are required in order to achieve the desired goal of high primary washing power with surfactants based on sodium disalts of the type described.
  • the subject of the invention in the most general embodiment is the use of sodium perborate together with at least approximately equal proportions of sodium sulfate, sodium zeolite and / or sodium tripolyphosphate (STP) and, if desired, further alkalizing sodium alkaline builder components for textile detergents as multi-component builders for enhancing the primary washing power of sodium disalphases alpha -sulfonated fatty acids of natural or synthetic origin, in particular the chain length range of C10 ⁇ 22 - hereinafter referred to simply as "sodium disalts" - when used as a detergent surfactant component in solid and / or liquid detergents and cleaning agents for textiles (detergent concentrates) , wherein the content of sodium perborate in the detergent concentrate is at least about 15% by weight and the content of sodium disalts is selected so that Nat rium disalt contents in the wash liquor of at least about 1 g / l are formed.
  • STP sodium tripolyphosphate
  • the sodium disalt content in the detergent concentrate is preferably selected so that when it is used as intended, sodium disalt contents of at least about 1.5 g / l and in particular at least about 1.7 g / l are formed in the aqueous wash liquor.
  • Working with sodium disaline contents in the wash liquor in the range of about 2 g / l and more can be particularly expedient.
  • sodium disaline contents are necessary for the formation of a high primary washing power Wash liquor in the range of approximately 1.7-3.5 g / l is sufficient, in particular those in the range of approximately 2-3 g / l, although the use of even higher amounts of sodium disalcohols means that the primary washing power in individual cases - taking into account the following Information - can be further strengthened.
  • the preferred sodium disalts for the use according to the invention are derived from saturated alpha-sulfofatty acids in the range C14 ⁇ 18 and in particular from the corresponding C 16/18 acids or the corresponding acid mixtures.
  • a very important builder component for increasing the primary washing power of sodium disalts when used as the only or essential detergent component in detergent mixtures is sodium perborate, which is usually used in the form of crystalline materials - tetrahydrate and / or monohydrate - in fine crystalline form.
  • sodium perborate of this type is in itself a conventional component in heavy duty laundry detergents in the European sector, which is however assigned a very specific meaning: The sodium perborate serves as a supplier of active oxygen or oxygen peroxide and is therefore the conventional detergent component for removing bleachable soiling.
  • perborate In conventional heavy duty laundry detergents, perborate is mostly used in combination with activators for triggering the bleaching action, in particular in combination with tetraacetylethylene diamine (TAED) or tetraacetylglycoluril (TAGU). It has been shown that the sodium perborate makes an important contribution to achieving the object according to the invention - raising the primary washing power of the sodium disalts concerned here to the standard of brand detergents customary today, which goes beyond its additional persistent bleaching action.
  • TAED tetraacetylethylene diamine
  • TAGU tetraacetylglycoluril
  • sodium perborate alone, but especially sodium perborate in Abmi Schung with the other cobuilder components mentioned sodium sulfate, sodium zeolite and / or STP leads to a noticeable increase in the primary washing power of washing liquors containing sodium disalts in the sense according to the invention, regardless of a possible influence on bleachable soiling.
  • the perborate range in the detergent concentrate can be particularly suitable at contents of about 18-25% by weight.
  • the content of the combination of builder substances which reinforce the primary washing power namely sodium perborate together with sodium sulfate, sodium zeolite and / or STP, to at least about 25% by weight and in particular to at least 30% by weight.
  • appropriate proportions of these substance mixtures in the range of about 25-80% by weight and in particular amounts in the range of about 30-70% by weight are suitable. All percentages by weight relate to the total weight of the detergent concentrate.
  • the content of the builder components sodium perborate in a mixture with sodium sulfate, sodium zeolite and / or STP is preferably set according to the invention in the detergent concentrates such that when the detergent concentrates are used as intended, the contents of these primary detergency boosters total at least about 2.5 g / l and preferably about 3 - 10 g / l are formed in the aqueous wash liquor.
  • Working with a wash liquor content of this inorganic builder combination in the range of about 3-8 g / l can be particularly preferred.
  • the teaching according to the invention is based on the surprising finding that, in the case of textile detergents of the type concerned here, which contain sodium disalts as active surfactant component, high results of the primary washing power can be obtained if, on the one hand, comparatively high contents of the disalt surfactant component are used in the wash liquor and, on the other hand, their effectiveness is increased by the use of the specified mineral builder components.
  • the primary washing power of detergents of the type affected here only increases in the usual range for the surfactant content of aqueous washing liquors under European conditions - surfactant amounts up to about 1.2 g / l or even up to about 1.5 g / l - with increasing amounts of surfactant very moderate, as long as sodium disalts of the type concerned are used as a detergent surfactant component. Even with increasing amounts of builder components, there is initially no substantial increase in the level of the primary washing power. The standard commercial laundry detergent appears unattainable.
  • sodium sulfate is also tends to have the same effect with regard to the builder effect in the area of high sodium disalt concentrations in the wash liquor as STP mentioned here. Based on these facts, it can only be concluded that sodium disalts and the washing and cleaning effects they cause on textiles are washing-active components or phenomena of their own kind that cannot easily be adapted to the previous picture of surfactant chemistry.
  • the preferred content of sodium disalts in the detergent concentrates is in the range from about 10 to 40% by weight and in particular about 15 to 30% by weight, with amounts in the range from about 17 to 25% by weight again being particularly suitable can.
  • Detergent concentrates of this type are suitable for a nominal dosage in the formation of the aqueous detergent solution in the range of at least about 7.5 g / l of detergent liquor and in particular in the range of about 7.5-15 g / l.
  • Typical dosages, in particular for solid detergents of the type described are in the range of about 10 g / l under European conditions, for example in the range of about 8-12 g / l.
  • the detergent concentrates according to the invention and thus the aqueous wash liquors used can contain further detergent surfactants and / or detergent boosters.
  • the amount of such detergent-active cosurfactants is at most approximately the same or preferably less than the amount of sodium disaline present in the detergent.
  • the amount of such additional cosurfactants does not, or not significantly, exceed about 80% by weight, and preferably about 60% by weight, of the sodium disalting amount.
  • the amount of detersive cosurfactants preferably makes up no more than about 50% by weight of the amount of sodium disalt used, with substantially smaller amounts, for example not more than 35% by weight and in particular not more than 20% by weight. can be particularly suitable.
  • the selection according to the invention is determined by the use of cosurfactants with the lowest possible toxicity - determined, for example, using the aforementioned aquatic toxicity model - and / or the use of the smallest possible amounts of such cosurfactants.
  • cosurfactants all the usual, in particular anionic and / or nonionic, surfactant components in the detergent sector are suitable for this use as cosurfactants.
  • cosurfactants can be fatty alcohol sulfates, in particular tallow sulfate, soaps and / or alkylglycosides, but also selected detergent boosters, for example those from the class of the fatty acid alkanolamides.
  • fatty acid soaps in particular sodium soaps from natural and / or synthetic fatty acids in the C number range of C10 ⁇ 22, in particular C12 ⁇ 18 and particularly preferably C 16/18, are important cosurfactants to the sodium disalts in the sense of the teaching according to the invention.
  • the sodium disalts on the one hand and the soaps used as cosurfactants on the other hand can be derived from the same natural and / or synthetic, in particular saturated, fatty acids or fatty acid mixtures. It is clear that considerable relief is obtained here, in particular for the production of corresponding surfactant mixtures, by selective partial sulfonation of a starting material containing carboxylic acids or carboxylic acid derivatives.
  • the use of the detergent surfactants based on ABS or LAS, which are widely used today, is dispensed with.
  • the detergent concentrates in the detergent concentrates according to the invention can be increased by using additional conventional builder components.
  • Sodium-alkaline builder components such as water glass and / or soda are particularly suitable here.
  • Water glass, ie soluble sodium silicate, can be used, for example, in amounts of up to about 15% by weight. Suitable amounts for the soda additional lie z. B. in the range of 5-35 wt .-%.
  • Calcium complex-binding compounds such as EDTA, NTA and / or polycarboxylates, which are known from conventional detergent technology, are also suitable.
  • the action according to the invention also provides for the use of swellable, finely divided sheet silicates, in particular from the class of natural and / or synthetic crystalline smectites with a strongly swellable layer structure.
  • swellable, finely divided sheet silicates in particular from the class of natural and / or synthetic crystalline smectites with a strongly swellable layer structure.
  • Mica-like layered silicates with a three-layer structure from the smectite group, such as montmorillonite, hectorite, saponite, beidellite and comparable compounds, are particularly suitable.
  • Bentonite is a suitable natural feed material, which is known to contain the majority of layered silicate of the montmorillonite structure.
  • Corresponding smectite clays are available under the most varied trade names on the market. Examples are the materials which are sold under the trade names “Laponite RD”, “Dis-Thix-Extra”, “Thixogel”, “Softclark” or under other known trade names.
  • the amount of this swellable layered silicate with a swaying action in the detergent concentrates according to the invention is in the range from about 3 to 25% by weight, preferably in the range from about 3 to 15% by weight and in particular within the range from about 5 to 10% by weight .
  • these additives also have a certain builder effect with regard to the primary washing power.
  • the additional advantage of a washing bath finish can be exploited, as described in detail in the earlier application mentioned P 36 04 039.8 (D 7537).
  • the detergent concentrates of the invention may be liquid detergents or solid materials.
  • Solid multi-component detergent mixtures are the generally preferred embodiment. Powdery and / or granular materials can be of particular importance.
  • a phosphate-free washing powder base formulation is mixed with gradually increasing amounts of the disodium salt of the hardened tallow fatty acid (C 16/18 ).
  • the washing powders produced in this way have the following composition: x% by weight of tallow fatty acid sodium disalt 4.0% by weight of coconut fatty acid monoethanolamide (Comperlan 100) 7.5% by weight of water glass (Portil N) 22.0% by weight sodium perborate 0.5% by weight carboxymethyl cellulose (CMC) 0.2% by weight of ethylenediamine tetraacetic acid (EDTA) 30.0% by weight sodium sulfate
  • the disodium salt content is increased in the range from 0 to 30% by weight in steps of 5% by weight.
  • Launderometer washing tests are carried out with the washing powders thus produced under the following conditions: Temperature 60 ° C, water hardness 16 ° dH, liquor ratio 1:30, 10 steel balls, washing time 30 minutes, rinsing time 4 x 30 seconds.
  • Standard test fabrics based on polyester / cotton (H-SH-PBV) soiled with dust / skin oil are washed.
  • the washing powder is dosed in the respective washing test in an amount of 7.5 g washing powder / l aqueous washing liquor.
  • the washing capacity is checked as a function of the disaline content by determining the degree of lightening on the washed goods (% remission determined using the Elrephomat from Carl Zeiss, Oberkochem, FRG). The values determined are summarized in Table 1 below.
  • the water value determined without the addition of washing powder under the specified washing conditions is 27.3% remission, a high-performance brand detergent delivers a remission value of 77.4 under the same washing conditions.
  • Table 1 % Sodium disalt in washing powder % Remission 0 30.5 5 35.5 10th 38.6 15 41.8 20th 66.2 25th 73.6 30th 76.2
  • FIG. 1 shows particularly clearly the sudden increase in the primary washing power in the range of about 1 to 1.5 g of active substance (AS) disalt - correspondingly with the washing powder dosage chosen the disaline content of about 15-20% AS in the washing powder.
  • AS active substance
  • Washing powders are produced according to the basic recipe of Example 1 with a content of 20% by weight (AS) sodium disalt.
  • AS 20% by weight
  • the sodium sulfate content is now gradually replaced by crystalline zeolite NaA (detergent quality) and the zeolite NaA content is increased to 40% by weight in an additional detergent formulation.
  • the inorganic builder salts mentioned as the last position of this detergent formulation are varied within the framework of the teaching according to the invention and compared with a control experiment which omits the use of this detergent component.
  • the washing results obtained are determined under the washing conditions mentioned in Example 2 (dosage of the washing powder 7.5 g / l). They are summarized in Table 3 below.
  • Example 1 To determine the influence of detergent boosters (WKV) used in small quantities, various washing powder mixtures based on sodium disaline are compiled according to the recipe from Example 1. In a first test series, the sodium disaline content is set to 10% by weight (AS), in a second test series this sodium disaline content (AS) is set to 20% by weight of the detergent concentrate.
  • AS sodium disaline content
  • washing tests are carried out under the conditions of the previous examples on H-SH-PBV test rags in a launderometer.
  • the washing powders used in each case are modified by the addition of various types of detergency booster shown in Table 4 below.
  • Each detergent booster is in turn added to the basic formulation in the proportions of 2% by weight, 4% by weight and 6% by weight WKV.
  • the dosage of the respective washing powder is 7.5 g / l.
  • AS 10% by weight
  • the lower limit for the disalt in the washing liquor of about 1 g / l defined according to the invention is not reached, while in the test series with a Content of 20 wt .-% (AS) sodium disalt in the detergent concentrate, the sodium disalt contents in the wash liquor are about 1.5 g / l.
  • Table 4 WKV number No WKV 1 2nd 3rd 4th 5 Branded laundry detergent 10% (AS) disalt 2% WKV 36.2 37.2 36.8 35.9 39.6 4% WKV 32.7 38.6 44.1 38.8 40.2 46.4 6% WKV 39.7 47.6 41.1 42.2 61.0 76.3 20% (AS) disalz7 2% WKV 73.2 76.2 75.0 74.7 75.5 4% WKV 69.5 76.2 76.3 75.6 77.3 75.9 6% WKV 74.5 73.9 75.8 77.2 76.5
  • This basic formulation is mixed with the detergent surfactant components listed below, with this amount of surfactant being gradually increased - in each case 2% by weight additive - in the range from 0 to 10% by weight additional surfactant.
  • additional surfactants are used: ABS (Maranil A 55) Tallow sulfate (sulfopone T 55) coconut sulfate (Sulfopon K 35) Fatty alcohol ether sulfate (Texapon NSO) Ester sulfonate (Texin ES 68) Alkyl glucoside (V 13S) Nonionic surfactant (Dehydol LT 7)
  • the washing conditions in launderometer washing correspond to the information in Example 1. Dosage of the washing powder in each case 7.5 g / l.
  • the basic detergent formulation 4.0% by weight of Comperlan 100 7.0% by weight of Portil N 22.0% by weight sodium perborate 0.5 wt% CMC 0.2% by weight EDTA on the one hand with increasing amounts of sodium disalt (10 - 40% by weight (AS) disalt in steps of 10% by weight) and at the same time with increasing amounts of sodium sulfate in the range of 0 - 60% by weight sodium sulfate ( levels of 10% by weight) were also increased here.
  • AS 40% by weight
  • Table 6 % By weight (AS) disalt % By weight Na2SO4 0 10th 20th 30th 40 50 60 10th 38.0 38.7 38.5 39.9 40.3 40.3 42.4 20th 60.6 65.3 68.7 71.3 75.6 74.8 74.5 30th 76.2 76.5 74.6 74.5 74.4 74.4 74.3 40 74.9 75.0 75.7 73.6 83.8 74.3 75.2
  • Example 6 The series examinations of Example 6 are repeated. In the new experiments, however, the sodium sulfate is replaced by crystalline zeolite NaA. The test conditions are otherwise the same as in Example 6.
  • Table 7 % By weight (AS) disalt Wt% zeolite NaA 0 10th 20th 30th 40 50 60 10th 37.4 44.2 48.9 53.7 57.0 63.1 66.6 20th 59.9 63.6 71.2 75.3 75.3 75.2 75.3 30th 74.9 77.3 77.3 76.8 76.7 76.0 75.8 40 75.3 75.2 76.0 74.8 74.3 74.3 74.1
  • washing powder composed exclusively of disodium salt of tallow fatty acid (C 16/18 ) and soda.
  • the washing conditions correspond to the information in the previous examples at a dosage of 7.5 g washing powder / l washing liquor.
  • the reflectance values determined on the washed and dried test textiles are summarized in Table 8 below. It can be seen that in a detergent constructed according to the invention, it is possible to activate the washing power in the range of 75% remission solely by adding soda, without the need to use further surfactant components with possibly undesirable effects in the wastewater problem.
  • Table 8 % By weight soda 0 10th 20th Disalz + soda 35.3 49.4 55.2 Disalz + soda + perborate content 53.6 58.6 62.9 Disalt + soda + perborate + Na2SO4 (30% by weight) 68.6 74.5 74.9

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  • 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)
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EP88112291A 1987-08-07 1988-07-29 Agents de lavage et de nettoyage pour le linge Withdrawn EP0302402A3 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3726326 1987-08-07
DE19873726326 DE3726326A1 (de) 1987-08-07 1987-08-07 Verbesserte wasch- und reinigungsmittel fuer textilien (ii)

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EP0302402A2 true EP0302402A2 (fr) 1989-02-08
EP0302402A3 EP0302402A3 (fr) 1989-11-29

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JP (1) JPS6466297A (fr)
KR (1) KR890003937A (fr)
DE (1) DE3726326A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5317896A (en) * 1992-03-13 1994-06-07 American Sterilizer Company Method of detecting liquid in a sterilization system
US5508258A (en) * 1990-08-03 1996-04-16 Henkel Kommanditgesellschaft Auf Aktien Use of surface-active alpha-sulfo-fatty acid di-salts in water and oil based drilling fluids and other drill-hole treatment agents
US5508009A (en) * 1992-03-13 1996-04-16 American Sterilizer Company Optimum hydrogen peroxide vapor sterilization system
US5534221A (en) * 1992-03-13 1996-07-09 American Sterilizer Company Device and system for sterilizing objects
WO1997011143A3 (fr) * 1995-09-18 1997-04-24 Stepan Co Compositions detergentes tres puissantes comprenant des sels d'esters methyliques alpha sulfones d'acide gras et utilisation des sels d'acides gras alpha sulfones pour inhiber la redeposition des salissures sur le tissu

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7820612B2 (en) * 2006-06-19 2010-10-26 The Procter & Gamble Company Laundry detergent containing methyl ester sulfonate

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3632517A (en) * 1970-08-21 1972-01-04 Us Agriculture Synergistic tallow-based detergent compositions
GB1368736A (en) * 1970-09-09 1974-10-02 Unilever Ltd Detergent compositions
DE3604039A1 (de) * 1986-02-08 1987-08-20 Henkel Kgaa Textil-wasch- und reinigungsmittel

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5508258A (en) * 1990-08-03 1996-04-16 Henkel Kommanditgesellschaft Auf Aktien Use of surface-active alpha-sulfo-fatty acid di-salts in water and oil based drilling fluids and other drill-hole treatment agents
US5317896A (en) * 1992-03-13 1994-06-07 American Sterilizer Company Method of detecting liquid in a sterilization system
US5508009A (en) * 1992-03-13 1996-04-16 American Sterilizer Company Optimum hydrogen peroxide vapor sterilization system
US5534221A (en) * 1992-03-13 1996-07-09 American Sterilizer Company Device and system for sterilizing objects
WO1997011143A3 (fr) * 1995-09-18 1997-04-24 Stepan Co Compositions detergentes tres puissantes comprenant des sels d'esters methyliques alpha sulfones d'acide gras et utilisation des sels d'acides gras alpha sulfones pour inhiber la redeposition des salissures sur le tissu

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EP0302402A3 (fr) 1989-11-29
KR890003937A (ko) 1989-04-18
JPS6466297A (en) 1989-03-13
DE3726326A1 (de) 1989-02-16

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