WO2008148502A1 - Particules solides d'activateurs de blanchiment hydrophobes - Google Patents

Particules solides d'activateurs de blanchiment hydrophobes Download PDF

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Publication number
WO2008148502A1
WO2008148502A1 PCT/EP2008/004294 EP2008004294W WO2008148502A1 WO 2008148502 A1 WO2008148502 A1 WO 2008148502A1 EP 2008004294 W EP2008004294 W EP 2008004294W WO 2008148502 A1 WO2008148502 A1 WO 2008148502A1
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WO
WIPO (PCT)
Prior art keywords
bleach activators
solid particles
spray
hydrophobic bleach
hydrophobic
Prior art date
Application number
PCT/EP2008/004294
Other languages
German (de)
English (en)
Inventor
Gerd Reinhardt
Georg Borchers
Andreas Schottstedt
Original Assignee
Clariant International Ltd
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 Clariant International Ltd filed Critical Clariant International Ltd
Publication of WO2008148502A1 publication Critical patent/WO2008148502A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/41—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton
    • C07C309/42—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • 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
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/391—Oxygen-containing 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3915—Sulfur-containing 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3935—Bleach activators or bleach catalysts granulated, coated or protected

Definitions

  • the invention relates to hydrophobic bleach activators with improved bleaching performance for use in detergents, cleaners and disinfectants.
  • Inorganic peroxygen compounds particularly hydrogen peroxide and solid peroxygen compounds which dissolve in water to release hydrogen peroxide, such as sodium perborate and sodium carbonate perhydrate, have long been used as oxidizing agents for disinfecting and bleaching purposes.
  • the oxidation effect of these substances in dilute solutions depends strongly on the temperature; Thus, for example, with HbO 2 or perborate in alkaline bleaching liquors only at temperatures above about 80 0 C, a sufficiently fast bleaching of soiled textiles.
  • N- or O-acyl compounds for example polyacylated alkylenediamines, in particular tetraacetylethylenediamine and tetraacetylglycoluril, N-acylated hydantoins, hydrazides, triazoles, hydrotriazines, urazoles.
  • bleach activators are essential constituents in powdered or tableted detergents, spot salts or machine dishwashing detergents. In addition, they can also be used in suspended form in aqueous and anhydrous liquid detergents.
  • the achievable bleaching result is essentially determined by the water-solubility of the activator, the structure of the compound to be perhydrolyzed, the type and reactivity of the peracid formed, and optionally by the formulation of the activator particle.
  • wash cycle times, good solubility, and effective drug release of the activator play an essential role in achieving sustainable bleaching performance. Poor solubility of the activator can lead to a completely insufficient washing result due to insufficient use of the components of the bleaching system. If one considers the dissolution process of the bleach activator, then it is shown in many cases that the dissolving behavior can be influenced by the way in which it is made up. Especially in the case of hydrophobic bleach activators, e.g. Lauroyloxybenzenesulfonic acid sodium (LOBS) or decanoyloxybenzoic acid (DOBA) raises the problem of poor water solubility, with the resulting release profile being sustainably affected by particle size. With increasing particle size is expected to delay the drug release. This has the consequence that in the manufacture of LOBS or DOBA the adjustment of the particle sizes is of great importance. Considering in this context introduced method of synthesis (from
  • Carboxylic acid chlorides and Hydroxybenzolklarederivaten and workup of hydrophobic activators, it is usually carried out at the end for solids isolation filtration and drying of the solid.
  • solids isolation filtration and drying of the solid For common apparatus, such. As pressure filter and paddle dryer, agglomeration and compression of the primary particles is unavoidable. This has the consequence that additional processing steps are necessary for setting the desired particle sizes.
  • the dried bleach activator must be screened and / or ground to the appropriate particle size Depending on the available equipment, different interconnections of screening and comminution are conceivable.
  • the packaging process according to the invention offers the advantage of a better product quality compared to the methods introduced, in particular with regard to improved water solubility.
  • a wet filter cake usually find contact dryer, such.
  • paddle dryer or Taumeltrock ⁇ er application depending on the degree of dehumidification and mixing of the filter cake different
  • Drying residence times in the range of a few minutes to a few hours are necessary.
  • the still moist product is exposed to elevated temperatures for a certain time, which may result in degradation of the active ingredient by hydrolysis and possibly also discoloration of the product. A loss of quality of the dried activator can thus not be excluded.
  • Significantly more favorable conditions, however, are achieved in the spray-drying process according to the invention.
  • the maximum product temperature is significantly determined by the outlet temperature of the drying gas, which can be chosen much lower considering the moisture content to be maintained than at the dryer inlet.
  • the drying is very fast, so that the product is only in the dryer for very short residence times, usually in seconds.
  • the method according to the invention thus offers the advantages of improved performance and improved product quality as well as simplified process control by reducing the process steps.
  • the invention therefore relates to solid particles of hydrophobic bleach activators of the general formula I
  • RC 7 -Cn-alkyl and X is -SO 3 Na, -COOH or -COONa, characterized in that these solid particles are obtained by spray-drying an aqueous slurry or a solution of the hydrophobic bleach activator, wherein in a particular embodiment, these particles in A subsequent step can still be encapsulated and / or granulated.
  • hydrophobic bleach activators are particularly preferred.
  • LABS Lauroyloxybenzenesulfonic acid
  • DOBA decanoyloxybenzoic acid
  • DOBA-Na sodium decanolyoxybenzoate
  • NOBA nonanoyloxybenzoic acid
  • the bleach activators thus prepared are used directly as a fine-grained powder together with a hydrogen peroxide-generating substance as a bleaching agent in solid or liquid detergents, cleaners and disinfectants.
  • the solid particles obtained by spray-drying are further compounded. This packaging is preferably in a granulation and / or a coating as described below.
  • bleaching is understood here to mean both the bleaching of dirt located on the textile surface and the bleaching of dirt located in the wash liquor and detached from the textile surface. Furthermore, the mixtures according to the invention find use in commercial laundries, in wood and paper bleaching, in the bleaching of cotton and in disinfectants. Spray drying
  • Spray drying processes are well known to those skilled in the art and can typically be carried out in spray towers but also fluidized bed apparatuses.
  • the material to be dried is sprayed in the form of an aqueous solution or slurry at the top of the spray tower.
  • a spray liquid with favorable properties for the process, such.
  • viscosity, distribution of solids in a suspension it may be necessary to treat the liquid accordingly and / or add suitable auxiliaries.
  • the treatment of the spray can z. B. by a temperature control or include the passage of a homogenization step.
  • the distribution of solids in a spray slurry or the surface tension can be influenced.
  • various systems are available, such as single-, dual- or multi-substance nozzles or atomizer disks, with which fine liquid droplets are produced.
  • the drying is carried out by hot gas, which is passed in cocurrent or countercurrent to the direction of spray through the tower.
  • the dried particles are separated from the gas stream after the dryer, usually with the help of cyclones and / or dust filters.
  • the drying process is primarily determined by the temperature profile of the inlet and outlet temperatures. Care must be taken to ensure that, on the one hand, the inlet temperature is not too high and the outlet temperature is not too low.
  • additives which can have binding, stabilizing and / or supplementary function are added in these granulation processes.
  • the binder material is often added in liquid form, but can also be registered as a solid, which is activated in the granulator by an auxiliary liquid (usually water).
  • a fluidized bed process in which the solution or slurry of the activator is transferred directly into a granulate.
  • a temperature control and / or dilution can likewise be carried out here.
  • the optionally added additives they can, in addition to a binder function, also have the task of stabilizing or supplementing the actual active substance.
  • one or more additives may be separately metered into the process in solid form.
  • the dust content of finished granules, as they are usually incurred, can be recycled as a solid in the fluidized bed. This recycling of the dust content is basically possible in all process variants for granulation.
  • the separate solids dosage allows z. B. the targeted supply of a carrier material for receiving sticky active substances.
  • the separate solids feed may prove to be a control instrument for granule growth in the process.
  • the described fluidized bed processes can be carried out in apparatuses which are designed both with round and with rectangular geometries.
  • the mixer granulation of the activator spray powder and the other components can be carried out in conventional, batch or continuous mixing devices, which are usually equipped with rotating mixing devices.
  • a mixer moderately operating devices such.
  • plowshare mixer Lödige KM types, Drais K-T types
  • intensive mixers eg Eirich, Schugi, Lödige CB types, Drais K-TT types
  • the residence times in the mixer granulation are preferably 0.5 s to 20 min, more preferably 2 s to 10 min.
  • a drying (for solvent) or cooling (for melting) step adjoins the granulating step in order to avoid sticking of the granules.
  • the aftertreatment preferably takes place in a fluidized bed apparatus. Subsequently, the coarse grain and the fine grain fraction is separated by sieving. The coarse grain alien! is crushed by grinding and fed as well as the fine grain content of a renewed granulation process.
  • Granulation with the aid of a plasticizer :
  • the solid activator is mixed with one or more plastification substances.
  • Other solid and liquid additives are also possible.
  • the plasticizing substances can be introduced in liquid form (solvent or usually water) or in melt form. Depending on the plasticizing system, attention must be paid in the process to a particularly careful temperature control (mixture with melt) or precise control of the moisture balance (mixture with solvent / water) in order to avoid an undesired change in the plasticity of the mixture (especially decrease by cooling, solidification or drying out).
  • the liquid plasticizer is intensively mixed with the powdered activator and optionally the other additives, so that a plastically deformable mass is formed.
  • the mixing step can take place in the abovementioned mixing apparatuses, but also kneaders or special extruder types (eg, Extrud-o-mix from Hosokawa-Bepex Corp.) are conceivable.
  • the granulation mass is then pressed by means of tools through the nozzle bores of a press die, so that cylindrically shaped extrudates are formed.
  • Suitable apparatuses for the extrusion process are ring roller presses (for example from Schlüter), edge mills (for example from Amandus-Kahl) and extruders, designed as single-shaft machines (for example from Hosokawa-Bepex, Fuji Paudal) or preferably as a twin-screw extruder (eg from the company Handle).
  • the choice of the diameter of the nozzle bore depends on the individual case and is typically in the range of 0.7 - 4 mm.
  • the exiting extrudates are to be comminuted by a post-processing step to the desired length or particle size.
  • the particle diameter is between 0.2 mm and 2 mm, preferably between 0.5 mm and 0.8 mm, the particle length in the range of 0.5 mm to 3.5 mm, ideally between 0.9 mm and 2 , 5 mm.
  • the length or size adjustment of the granules can, for example, by fixed Scraper blades, rotating blades, cutting wires or blades are made. To round off the cut edges, the granulate can then be rounded again in a rounding device (eg from Glatt, Schlüter, Fuji-Paudal).
  • the extrudate is only roughly chipped and the extrudate strands are transferred directly to a ripper.
  • the further granulation takes place in Rondier Kunststoff, in a preferred embodiment, the process is carried out in cascade operation.
  • the size and shape of the particles can be influenced and brought about in the Rondier Kunststoff by several parameters.
  • the forming process is determined by the filling quantity, the temperature of the mixture, the residence time of the mixture in the Rondier, by the rotation speed of the Rondierintra, as well as by the plastic deformability of the mixture. With decreasing filling volume in the rounding device, shorter cylindrical granules and a narrower distribution of the particle sizes are obtained. With decreasing plasticity initially longer granules are obtained, with a further decrease in plasticity, the dust content increases sharply and targeted particle formation can not be achieved.
  • Solidification step required in which the solvent is removed or the melt is solidified.
  • this step is carried out in a fluidized bed apparatus which operates as a dryer or cooler as required.
  • the coarse grain and the fine grain fraction is separated by sieving.
  • the coarse grain fraction is comminuted by grinding and, like the fine grain fraction, fed to a renewed granulation process.
  • the pulverulent activator is optionally mixed with further preferably solid additives and this mixture compacted, then ground and then optionally sieved into individual grain fractions.
  • liquid additives may also be added to the mixture to a certain extent (eg up to 10%).
  • compacting aids are water glass, polyethylene glycols, nonionic surfactants, anionic surfactants, polycarboxylate copolymers, modified and / or unmodified celluloses, bentonites, hectorites, saponites and / or other detergent ingredients.
  • the compaction is preferably carried out on so-called roll compactors (eg from Hosokawa-Bepex, Alexanderwerk, Köppern).
  • roll compactors eg from Hosokawa-Bepex, Alexanderwerk, Köppern.
  • the roll profile can be on the one hand produce lumpy pellets or briquettes and on the other hand Preßschülpen. While the lumpy briquettes are usually separated only from the fines, the slugs must be crushed in a mill to the desired particle size.
  • screen and hammer mills eg from Hosokawa-Alpine, Hosokawa-Bepex
  • roll mills eg from Bauermeister, Bühler, Merz
  • the granules thus obtained are suitable directly for use in detergents and cleaners.
  • they can be provided with a coating shell according to methods known per se.
  • the granules in an additional step with a coated film-forming substance, whereby the product properties can be significantly influenced.
  • Suitable coating agents are all film-forming substances, such as waxes, silicones, fatty acids, fatty alcohols, soaps, anionic surfactants, nonionic surfactants, cationic surfactants, anionic and cationic polymers, and polyalkylene glycols.
  • Coating substances preferably having a melting point of 30-100 0 C is used. Examples of these are: C 8 -C 31 -fatty acids, for example lauric, myristic, stearic acid); C 8 -C 3 r fatty alcohols; Polyethylene glycols with a molecular weight of 1,000 to
  • further substances which do not soften or melt in this area can be in dissolved or suspended form, for example homopolymers, copolymers or graft copolymers of unsaturated carboxylic acids and / or sulfonic acids and their alkali metal salts, cellulose ethers, starch, starch ethers, polyvinylpyrrolidone; mono- and polybasic carboxylic acids, hydroxycarboxylic acids or ether carboxylic acids having 3 to 8 carbon atoms and salts thereof; Silicates, carbonates, bicarbonates, sulfates, phosphates, phosphonates.
  • the content of coating substance can be from 1 to 30% by weight, preferably from 5 to 15% by weight, based on the coated granules.
  • mixers For applying the coating substances, mixers (mechanically induced
  • Fluidized bed and fluidized bed apparatus (pneumatically induced fluidized bed) are used.
  • a mixer z. B. plowshare mixer continuous and batchwise
  • ring layer mixers or Schugi mixer possible.
  • the Heat treatment can be carried out using a mixer in a granule preheater and / or in the mixer directly and / or in a fluidized bed downstream of the mixer.
  • Granulated coolers or fluid bed coolers can be used to cool the coated granules.
  • the heat treatment takes place via the hot gas used for fluidization.
  • the granules coated by the fluidized-bed method can be cooled by a granulate cooler or a fluidized-bed cooler, similar to the mixing method. Both in the mixing process and in the fluidized bed process, the coating substance can be sprayed on a single-component or a Zweistoffdüsvorraum.
  • the optional temperament consists in one
  • Heat treatment at a temperature of 30 to 100 0 C, but equal to or below the melting or softening temperature of the respective shell substance. Preference is given to working at a temperature which is just below the melting or softening temperature.
  • the coating agents can be applied in the form of solutions or suspensions to the primary particles, which is possible in principle with the aforementioned apparatuses.
  • Fluidized bed apparatuses may preferably be used here, since they offer the advantage that liquid can be sprayed in at the same time and moisture dried off. This often results in increased flexibility in the process and in the achievable product quality.
  • the bleach activators according to the invention can be used in detergents, cleaners and disinfectants together with hydrogen peroxide or peroxygen compounds.
  • Essential components of such detergents, cleaners and disinfectants will be listed below.
  • the detergents and cleaning agents according to the invention may in principle contain all known ingredients customary in such agents, in addition to the activator particles according to the invention and a peroxygen compound.
  • the invention Agents may in particular contain builder substances, surface-active surfactants, peroxygen compounds, additional peroxygen activators or organic peracids, water-miscible organic solvents, sequestering agents, thickeners, preservatives, pearlescing agents, emulsifiers and enzymes, as well as special additives with color or fiber-sparing action.
  • Other auxiliaries such as electrolytes, pH regulators, silver corrosion inhibitors, foam regulators as well as dyes and fragrances are possible.
  • Suitable peroxygen compounds are hydrogen peroxide and under the washing and cleaning conditions hydrogen peroxide donating compounds such as alkali metal peroxides, organic peroxides such as urea-hydrogen peroxide adducts and inorganic persalts such as alkali metal perborates, percarbonates, perphosphates, persilicates, persulfates and peroxynitrite. Mixtures of two or more of these compounds are also suitable. Particularly preferred are sodium perborate tetrahydrate and in particular sodium perborate monohydrate and sodium percarbonate. Sodium perborate monohydrate is preferred for its good storage stability and good solubility in water. Sodium percarbonate may be preferred for environmental reasons.
  • Alkali hydroperoxides are another suitable group of peroxide compounds. Examples of these substances are cumene hydroperoxide and t-butyl hydroperoxide. Aliphatic or aromatic mono- or dipercarboxylic acids and the corresponding salts are suitable as peroxy compounds.
  • Examples of these are peroxynaphthoic acid, peroxylauric acid, peroxystearic acid, N, N-phthaloylaminoperoxycaproic acid, 1,12-diperoxydodecanedioic acid, 1,9-diperoxyazelaic acid, diperoxysebacic acid, diperoxyisophthalic acid, 2-decyldiperoxybutane-1,4-diacid and 4,4'-suifonyl-bisperoxybenzoic acid.
  • hydrophobic bleach activators In addition to the particles of hydrophobic bleach activators according to the invention, other particularly hydrophilic bleach activators may be present in the detergents and cleaners Bleach activators, preferably in the form of granules in the usual amounts (about 1 to 10 wt .-%) to be included.
  • Particularly suitable as further bleach activators are organic compounds having an O-acyl or N-acyl group, in particular acylated alkylenediamines, for example NNN'.N'-tetraacetylethylenediamine, acylated triazine derivatives, in particular 1,5-diacetyl-2,4-dioxohexahydroxy- 1, 3,5-triazine, acylated glycolurils, in particular tetraacetylglycoluril, and acylated sugar derivatives, in particular pentaacetylglucose (PAG), pentaacetylfructose, tetraacetylxylose and octaacetyllactose, as well as acetylated, optionally N-alkylated glucamine and gluconolactone and / or N-acylated lactams, for example N -Benzoylcaprolactam, but also quatern
  • sulfonimines open-chain or cyclic quaternary iminium compounds such as dihydroisoquinolinium betaines and / or other bleach-enhancing transition metal salts or mononuclear or polynuclear transition metal complexes with acyclic or macrocyclic ligands may also be included.
  • the detergents and cleaners may further contain the ingredients known in the art, as z. In Handbook of Detergents, Part D:
  • surfactants in particular anionic surfactants, nonionic surfactants and mixtures thereof, but also cationic, zwitterionic and amphoteric surfactants come into question.
  • Such surfactants are present in detergent compositions according to the invention in proportions of preferably from 1 to 50% by weight, in particular from 3 to 30% by weight, whereas in hard-surface cleaners normally lower proportions, that is to say amounts of up to 20% by weight. , in particular up to 10 wt .-%, and preferably in the range of 0.5 to 5 wt .-% are included.
  • Dishwashing detergents typically use low-foam compounds.
  • the detergents furthermore preferably contain at least one water-soluble and / or water-insoluble, organic and / or inorganic builder.
  • Example 2 Spray drying of an aqueous LOBS slurry
  • Example 4 Spray drying of an aqueous DOBA slurry
  • a LOBS powder prepared according to Comparative Example 1 was ground again and sieved to obtain a fraction having a grain size ⁇ 50 ⁇ m. The peracid release of this sample was compared with the peracid release of a LOBS sample prepared according to Example 3.
  • a DOBA powder prepared from moist DOBA filter cake analogous to Comparative Example 1 was ground again and sieved to obtain a fraction with a particle size ⁇ 50 microns.
  • the peracid release of this sample was compared with the peracid release of a DOBA sample prepared according to Example 4.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
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Abstract

L'invention concerne des particules solides d'activateurs de blanchiment hydrophobes représentés par la formule (1) dans laquelle R est C7-C11-alkyle et X est -SO3Na, -COOH ou -COONa. L'invention est caractérisée en ce que les particules solides sont obtenues par séchage par pulvérisation d'une suspension ou d'une solution aqueuse de ces activateurs de blanchiment hydrophobes. Les activateurs de blanchiment ainsi obtenus présentent une meilleure libération de peracide par rapport aux mêmes activateurs de blanchiment obtenus selon d'autres procédés.
PCT/EP2008/004294 2007-06-05 2008-05-30 Particules solides d'activateurs de blanchiment hydrophobes WO2008148502A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007026216.9 2007-06-05
DE200710026216 DE102007026216A1 (de) 2007-06-05 2007-06-05 Feste Partikel von hydrophoben Bleichaktivatoren

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Publication Number Publication Date
WO2008148502A1 true WO2008148502A1 (fr) 2008-12-11

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Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0140251A2 (fr) * 1983-10-19 1985-05-08 BASF Aktiengesellschaft Procédé pour la préparation de sels de métaux alcalins ou alcalino-terreux d'acides acyloxybenzènesulphoniques
US4537724A (en) * 1983-05-11 1985-08-27 Ethyl Corporation Alkanoyloxybenzenesulfonate salt production
EP0163224A1 (fr) * 1984-05-26 1985-12-04 BASF Aktiengesellschaft Procédé de préparation d'acides acyloxybenzènesulfoniques
DE3524052A1 (de) * 1985-07-05 1987-01-08 Hoechst Ag Verfahren zur herstellung von acyloxybenzolsulfonsaeuren und deren salzen
DE3530101A1 (de) * 1985-08-23 1987-02-26 Hoechst Ag Verfahren zur herstellung von acyloxybenzolsulfonaten
DE3538143A1 (de) * 1985-10-26 1987-04-30 Hoechst Ag Verfahren zur herstellung von acyloxibenzolsulfonsaeuren und deren salzen
US4692279A (en) * 1985-04-15 1987-09-08 Stepan Company Preparation of acyloxy benzene sulfonate
US4721805A (en) * 1985-04-15 1988-01-26 Stepan Company Preparation of acyloxy benzene sulfonate
US6015784A (en) * 1996-03-08 2000-01-18 The Procter & Gamble Company Secondary alkyl sulfate particles with improved solubility by compaction/coating process
DE19844522A1 (de) * 1998-09-29 2000-03-30 Henkel Kgaa Granulationsverfahren

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4537724A (en) * 1983-05-11 1985-08-27 Ethyl Corporation Alkanoyloxybenzenesulfonate salt production
EP0140251A2 (fr) * 1983-10-19 1985-05-08 BASF Aktiengesellschaft Procédé pour la préparation de sels de métaux alcalins ou alcalino-terreux d'acides acyloxybenzènesulphoniques
EP0163224A1 (fr) * 1984-05-26 1985-12-04 BASF Aktiengesellschaft Procédé de préparation d'acides acyloxybenzènesulfoniques
US4692279A (en) * 1985-04-15 1987-09-08 Stepan Company Preparation of acyloxy benzene sulfonate
US4721805A (en) * 1985-04-15 1988-01-26 Stepan Company Preparation of acyloxy benzene sulfonate
DE3524052A1 (de) * 1985-07-05 1987-01-08 Hoechst Ag Verfahren zur herstellung von acyloxybenzolsulfonsaeuren und deren salzen
DE3530101A1 (de) * 1985-08-23 1987-02-26 Hoechst Ag Verfahren zur herstellung von acyloxybenzolsulfonaten
DE3538143A1 (de) * 1985-10-26 1987-04-30 Hoechst Ag Verfahren zur herstellung von acyloxibenzolsulfonsaeuren und deren salzen
US6015784A (en) * 1996-03-08 2000-01-18 The Procter & Gamble Company Secondary alkyl sulfate particles with improved solubility by compaction/coating process
DE19844522A1 (de) * 1998-09-29 2000-03-30 Henkel Kgaa Granulationsverfahren

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