DE3434468A1 - Process for preparing powdered, storable hydrogen peroxide adducts - Google Patents

Process for preparing powdered, storable hydrogen peroxide adducts

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Publication number
DE3434468A1
DE3434468A1 DE19843434468 DE3434468A DE3434468A1 DE 3434468 A1 DE3434468 A1 DE 3434468A1 DE 19843434468 DE19843434468 DE 19843434468 DE 3434468 A DE3434468 A DE 3434468A DE 3434468 A1 DE3434468 A1 DE 3434468A1
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Germany
Prior art keywords
hydrogen peroxide
adducts
weight
molecular weight
peroxide adducts
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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Withdrawn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
DE19843434468
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German (de)
Inventor
Rolf 4047 Dormagen Lentfer
Dieter 4000 Düsseldorf Schrader
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
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Henkel AG and Co KGaA
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Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to DE19843434468 priority Critical patent/DE3434468A1/en
Publication of DE3434468A1 publication Critical patent/DE3434468A1/en
Withdrawn legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/08—Preparations for bleaching the hair
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/22—Peroxides; Oxygen; Ozone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B15/00—Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
    • C01B15/005—Stabilisation of the solid compounds subsequent to the preparation or to the crystallisation, by additives or by coating
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B15/00—Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
    • C01B15/055—Peroxyhydrates; Peroxyacids or salts thereof
    • C01B15/06—Peroxyhydrates; Peroxyacids or salts thereof containing sulfur
    • C01B15/08—Peroxysulfates
    • C01B15/085—Stabilisation of the solid compounds, subsequent to the preparation or to the crystallisation, by additives or by coating
    • 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
    • C11D3/3937—Stabilising agents

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Detergent Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The process for preparing powdered, flowable hydrogen peroxide adducts, especially urea perhydrate and/or melamine perhydrate, by dry mixing of the powdered adducts with a polyalkylene glycol having 2 or 3 carbon atoms in the alkylene group and having a mean molecular weight of 200-4,000 in an amount of 0.5-5% by weight results in products having longer shelf lives. The hydrogen peroxide adducts prepared according to the invention are preferably free of colloidal or microfine silicic acid.

Description

"Verfahren zur Herstellung pulverförmiger, lagerbestän-"Process for the production of powdery, storage-stable

diger Wasserstoffperoxid-Addukte" Wasserstoffperoxid bildet zahlreiche kristalline Anlagerungsprodukte an anorganische Salze sowie an kristalline organische Verbindungen. Als Beispiele seien Addukte an Natriumsulfat, Natriumacetat, Harnstoff, Melamin, Acetamid, Urethan, Succinimid, Asparagin, Hexamethylentetramin, Natriumformiat und an Natriumcitrat genannt. Viele dieser Addukte des Wasserstoffperoxids weisen nur eine begrenzte Lagerstabilität auf. Dies gilt auch für die technisch bedeutenden Addukte an Harnstoff und Melamin. Diese Perhydrate geben bei Lagerung, insbesondere bei erhöhter Temperatur, allmählich das angelagerte H202 ab.diger hydrogen peroxide adducts "Hydrogen peroxide forms numerous crystalline addition products with inorganic salts and with crystalline organic ones Links. Examples are adducts of sodium sulfate, sodium acetate, urea, Melamine, acetamide, urethane, succinimide, asparagine, hexamethylenetetramine, sodium formate and called sodium citrate. Many of these adducts of hydrogen peroxide exhibit only has a limited shelf life. This also applies to the technically important ones Adducts to urea and melamine. These perhydrates give on storage, in particular at elevated temperature, the accumulated H202 gradually decreases.

Es wurden zahlreiche Vorschläge gemacht, die Lagerstabilität von Wasserstoffperoxid-Addukten zu erhöhen; In DE-PS 68 12 05 wurde vorgeschlagen, das masserstoffperoxid-Harnstoff-Addukt mit wasserabstoßenden Mitteln z.B.Numerous proposals have been made as to the storage stability of hydrogen peroxide adducts to increase; In DE-PS 68 12 05 it was proposed that the solid peroxide-urea adduct with water repellants e.g.

mit Fetten oder Wachsen zu imprägnieren. In DE-PS 68 72 17 wurde der Zusatz von oberflchenaktiven Stoffen beschrieben. Nach US-PS 36 29 331 wird der Zusatz von Ethylendiamintetraessigsäure (EDTA) und Natriumdihydrogenphosphat zum Harnstoff-Peroxid empfohlen. Zur Verbesserung des Fließverhaltens sollen außerdem 3 bis 9 Gewichtsprozent kolloidaler Kieselsäure zugesetzt werden.to be impregnated with fats or waxes. In DE-PS 68 72 17 was the Addition of surface-active substances described. According to US-PS 36 29 331 is the Addition of ethylenediaminetetraacetic acid (EDTA) and sodium dihydrogen phosphate to the Urea peroxide recommended. To improve the flow behavior should also 3 to 9 percent by weight of colloidal silica can be added.

In DE-PS 11 69 901 wird ein Verfahren zur Herstellung von Wasserstoffperoxid enthaltenden Pasten beschrieben, bei welchem Wasserstoffperoxid oder Harnstoffperhydrat in Polyethylenoxiden gelöst werden.DE-PS 11 69 901 describes a process for the production of hydrogen peroxide containing pastes described in which hydrogen peroxide or urea perhydrate be dissolved in polyethylene oxides.

Die nach den bekannten Verfahren herstellbaren pulverförmigen Wasserstoffperoxid-Addukte sind in bezug auf die Lagerstabilität nicht befriedigend. Die unter Verwendung von Polyethylenoxiden herstellbaren Pasten sind, da sie keine Fließfähigkeit aufweisen, für viele Anwendungszwecke nicht brauchbar.The pulverulent hydrogen peroxide adducts which can be prepared by the known processes are unsatisfactory in terms of storage stability. The ones using Polyethylene oxides are pastes that can be produced, since they have no flowability, not usable for many purposes.

Es bestand daher die Aufgabe, ein Verfahren zu finden, welches die Herstellung von pulverförmigen Wasserstoffperoxid-Addukten mit verbesserter Lagerstabilität ermöglicht, ohne die Fließfähigkeit bzw. Rieselfähigkeit des Pulvers zu verschlechtern oder ein Verkleben und/oder Zusammenbacken zu verursachen.The task was therefore to find a method which Production of hydrogen peroxide adducts in powder form with improved storage stability made possible without impairing the flowability or pourability of the powder or to cause sticking and / or caking.

Es wurde gefunden, daß die Stabilisierung pulverförmiger Wasserstoffperoxidaddukte dadurch möglich ist, daß man pulverförmige Wasserstoffperoxid-Anlagerungsverbindungen mit einem Polyalkylenglycol mit 2 oder 3 C-Atomen in der Alkylengruppe und mit einem mittleren Molekulargewicht von 200 bis 4000 in einer Menge von 0,5 bis 5,0 Gewichtsprozent, bezogen auf das Gewicht des Pulvers trocken vermischt. Das trockene Vermischen kann vorteilhaft in der Weise geschehen, daß das Polyalkylenoxid im flüssigen Zustand, also gegebenenfalls nach Erwärmung über den Schmelzpunkt,auf das pulverförmige Wasserstoffperoxid-Addukt aufgesprüht wird.It has been found that the stabilization of powdered hydrogen peroxide adducts it is possible by using powdered hydrogen peroxide addition compounds with a polyalkylene glycol with 2 or 3 carbon atoms in the alkylene group and with a average molecular weight of 200 to 4000 in an amount of 0.5 to 5.0 percent by weight, dry mixed based on the weight of the powder. Can dry blending advantageously done in such a way that the polyalkylene oxide in the liquid state, so if necessary after heating above the melting point, to the powdery Hydrogen peroxide adduct is sprayed on.

Geeignet sind Polyethylenglycole, Polypropylenglycole, Mischpolymerisate aus Ethylenoxid und Propylenoxid z.B.Polyethylene glycols, polypropylene glycols and copolymers are suitable from ethylene oxide and propylene oxide e.g.

Ethylenoxidanlagerungsprodukte an Polypropylenoxid und Propylenoxidanlagerungsprodukte an Polyethylenoxide. Besonders vorteilhaft sind solche Polyalkylenglycole, die bei 20 OC flüssig und klar wasserlöslich sind. Solche bevorzugten Polyalkylenglycole sind die Polyethylenglycole und Polypropylenglycole, deren mittleres Molekulargewicht im Bereich von 200 bis 800 liegt. Besonders bevorzugt geeignet ist Polyethylenglycol mit einem mittleren Molekulargewicht von 400.Ethylene oxide addition products with polypropylene oxide and propylene oxide addition products to polyethylene oxides. Those polyalkylene glycols which are particularly advantageous are those which are used in 20 OC are liquid and clearly soluble in water. Such preferred polyalkylene glycols are the polyethylene glycols and polypropylene glycols, their average molecular weight ranges from 200 to 800. Polyethylene glycol is particularly preferred with an average molecular weight of 400.

Nach dem erfindungsgemäßen Verfahren werden pulverförmige Wasserstoffperoxid-Addukte mit guter Fließfahigkeit erhalten, die nicht zum Zusammenbacken neigen und die außerordentlich lagerstabil sind, Bevorzugt geeignet ist das erfindungsgemäße Verfahren zur Stabilisierung von Addukten des Wasserstoffperoxids an Harnstoff (Harnstoffperhydrat) und an Melamin (blelaminperhydrat).In the process according to the invention, powdered hydrogen peroxide adducts are obtained obtained with good flowability, which do not tend to cake and which are extremely are storage-stable, the process according to the invention is preferably suitable for stabilization of adducts of hydrogen peroxide with urea (urea perhydrate) and with melamine (blelamin perhydrate).

Diese Addukte lassen sich durch trockenes Vermischen oder Besprühen mit 1 bis 5 Gewichtsprozent eines Polyethylenglycols mit dem mittleren Molekulargewicht von 200 bis 800 sehr gut stabilisieren. Bei Verwendung von Polyethylenglycol mit dem mittleren Molekulargewicht von ca. 400 sind 1 bis 3 Gewichtsprozent ausreichend.These adducts can be dry mixed or sprayed with 1 to 5 weight percent of an average molecular weight polyethylene glycol Stabilize very well from 200 to 800. When using polyethylene glycol with with an average molecular weight of approx. 400, 1 to 3 percent by weight is sufficient.

Ein Zusatz von kclloidaler oder pyrogen erzeugter, mikrofeiner Kieselsäure zur Verbesserung des Fließverhaltens ist nicht nur überflüssig, sondern verschlechtert die Lagerstabilität der nach den erfinduncrsgemäßen Ver- fahren hergestellten Wasserstoffperoxid-Addukte. Ein weiterer Gegenstand der Erfindung sind daher pulverförmige, fließfähige und lagerstabile Wasserstoffperoxid-Addukte, die nach dem erfindungsgemäßen Verfahren stabilisiert und frei von kolloidaler oder mikrofeiner Kieselsäure sind.An addition of cloidal or pyrogenic, microfine silica to improve the flow behavior is not only superfluous, but deteriorated the storage stability of the according to the invention travel produced hydrogen peroxide adducts. Another object of the invention are therefore powdery, flowable and storage-stable hydrogen peroxide adducts, which are stabilized by the process according to the invention and free from colloidal or microfine silica.

Die erfindungsgemäßen Wasserstoffperoxid-Addukte eignen sich z.B. für die Herstellung von Oxidationshaarfärbemitteln, die durch Vermischen einer Zubereitung von Oxidationsfarbstoffvorprodukten mit Wasserstoffperoxid hergestellt werden. Für diesen Zweck ist bevorzugt ein nach den erfindungsgemäßen Verfahren stabilisiertes Harnstoff- oder Melamin-Perhydrat geeignet. Beim Auflösen dieser Wasserstoffperoxid-Addukte in Wasser oder wässrigen Zubereitungen wird das Wasserstoffperoxid in Freiheit gesetzt und steht dann für die Entwicklung der Oxidationsfarben zur Verfügung (vgl. Schimmel Briefs Nr. 337, April 1963).The hydrogen peroxide adducts according to the invention are suitable e.g. for the production of oxidation hair dyes by mixing a preparation of oxidation dye precursors with hydrogen peroxide. For this purpose is preferably one stabilized according to the method according to the invention Urea or melamine perhydrate suitable. When dissolving these hydrogen peroxide adducts The hydrogen peroxide is released in water or aqueous preparations and is then available for the development of the oxidation colors (cf. Schimmel Briefs No. 337, April 1963).

Andere Anwendungsgebiete für erfindungsgemäß hergestellte Wasserstoffperoxid-Addukte sind pulverförmige antiseptische Zubereitungen und Bleichmittel-Zubereitungen.Other areas of application for hydrogen peroxide adducts produced according to the invention are powdered antiseptic preparations and bleach preparations.

Die folgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern ohne ihn hierauf zu beschränken.The following examples are intended to further illustrate the subject matter of the invention explain without restricting it to this.

Beispiele Die Versuche wurden durchgeführt unter Verwendung eines Melamin-Perhydrats der Firma Peroxid-Chemie, einer Korngröße unter 1 mm.Examples The experiments were carried out using a Melamine perhydrates from Peroxid-Chemie, a particle size of less than 1 mm.

Versuchsdurchführung Je 10 Proben von je 5 g des unbehandelten bzw. vorbehandelten Melamin-Perhydrats wurden in Siegelrandbeutel aus einer Innenlage aus Polyethylen, einer Zwischenlage aus Aluminium und einer Hülle aus Panier abgefüllt und versiegelt (verschweißt). Kurz vor Abfüllung wurde der fI202-Anfangsgehalt bestimmt (Jodometrische Titration).Carrying out the experiment 10 samples of 5 g each of the untreated or pretreated melamine perhydrates were placed in sealed bags from an inner layer made of polyethylene, an intermediate layer made of aluminum and a shell made of breading and sealed (welded). Shortly before bottling, the initial fI202 content was determined (Iodometric titration).

0 Die Probebeutel wurden dann bei 45 C in einem thermostatisierten Schrank gelagert. Nach 12 Wochen wurde der Gewichtsverlust und der H202-Gehalt des Perhydrat-Pulvers erneut bestimmt. 0 The sample bags were then thermostated at 45 C Cabinet stored. After 12 weeks, the weight loss and the H202 content of the Perhydrate powder determined again.

Die Proben wurden wie folgt vorbehandelt: A: unbehandelt B: mit 2,0 Gewichtsprozent Polyethylenglycol 400 besprüht und gemischt C: mit 1,0 Gewichtsprozent Aerosil zu 200 gemischt D: mit 1,0 Gewichtsprozent Aerosil R 200 gemischt und mit 2,0 Gewichtsprozent Polyethylenglycol 400 besprüht und gemischt.The samples were pretreated as follows: A: untreated B: with 2.0 Weight percent polyethylene glycol 400 sprayed and mixed C: with 1.0 weight percent Aerosil mixed to 200 D: mixed with 1.0 percent by weight Aerosil R 200 and with 2.0 weight percent polyethylene glycol 400 sprayed and mixed.

Das Ergebnis der Prüfungen ist der folgenden Tabelle zu entnehmen (durchschnittlich von 10 Proben). A B C D H202-Anfangswert (Gewichtsprozent) 16,17 20,27 20,45 19,31 Gewichtsverlust nach 12 Wochen / 45 °C 0,04 0,07 g 0,5 g 0,57 g H202-Gehalt (Gew. %) nach 12 Wochen / 45 °C 14,7 20,1 13,25 1,4 Aussehen der unver- unver- stark teilweise Probebeutel ändert ändert gebläht aufgebläht The results of the tests are shown in the following table (on average from 10 samples). ABCD H202 initial value (Weight percent) 16.17 20.27 20.45 19.31 Weight loss after 12 weeks / 45 ° C 0.04 0.07 g 0.5 g 0.57 g H202 content (wt.%) after 12 weeks / 45 ° C 14.7 20.1 13.25 1.4 Appearance of the un- un- strongly partially Sample bag changes changes bloated bloated

Claims (4)

PatentansCrüche 1. Verfahren zur Herstellung pulverförmiger, fließfähiger Wasserstoffperoxid-Addukte, dadurch gekennzeichnet, daß man pulverförmige Wasserstoffperoxid-Anlagerungsverbindungen mit einem Polyalkylenglycol mit 2 oder 3 C-Atomen in der Alkylgruppe und mit einem mittleren Molekulargewicht von 200 bis 4000 in einer Menge von 0,5 bis 5,0 Gewichtsprozent trocken vermischt.Patent claims 1. Process for the production of powdery, flowable Hydrogen peroxide adducts, characterized in that pulverulent hydrogen peroxide addition compounds are used with a polyalkylene glycol with 2 or 3 carbon atoms in the alkyl group and with one average molecular weight of 200 to 4000 in an amount of 0.5 to 5.0 percent by weight dry mixed. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man pulverförmige Addukte von Wasserstoffperoxid an Harnstoff und/oder Melamin mit einem Polyethylenglycol mit einem mittleren Molekulargewicht von 200 bis 800 in einer Menge von 1 bis 5 Gewichtsprozent trocken vermischt.2. The method according to claim 1, characterized in that powdery Adducts of hydrogen peroxide to urea and / or melamine with a polyethylene glycol with an average molecular weight of 200 to 800 in an amount of 1 to 5 Weight percent dry mixed. 3. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß man das Wasserstoffperoxid-Addukt mit einem Polyethylenglycol mit einem mittleren Molekulargewicht von ca. 400 in einer Menge von 1 bis 3 Gewichtsprozent trocken vermischt.3. The method according to claim 1 or 2, characterized in that one the hydrogen peroxide adduct with a medium molecular weight polyethylene glycol from about 400 dry blended in an amount of 1 to 3 percent by weight. 4. Pulverförmige, fließfähige und lagerstabile Wasserstoffperoxid-Addukte, dadurch gekennzeichnet, daß sie nach einem der Verfahren gemäß Anspruch 1 bis 3 hergestellt und frei von kolloidaler oder mikrofeiner Kieselsäure sind.4. Powdery, flowable and storage-stable hydrogen peroxide adducts, characterized in that it according to one of the methods according to claims 1 to 3 and are free from colloidal or microfine silica.
DE19843434468 1984-09-20 1984-09-20 Process for preparing powdered, storable hydrogen peroxide adducts Withdrawn DE3434468A1 (en)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0257399A2 (en) * 1986-08-13 1988-03-02 Beratungslabor für die kosmetische und pharmazeutische Industrie Dipl.-Ing. Karlheinz Schrader Hair dyeing composition
EP0619114A1 (en) * 1993-04-05 1994-10-12 L'oreal Bleaching composition in granulate form for hair bleaching and process for preparing it
EP0663205A1 (en) * 1994-01-14 1995-07-19 L'oreal Cosmetic compositions for hair bleaching, process for their synthesis and their use
FR2716804A1 (en) * 1994-03-02 1995-09-08 Oreal Cosmetic compositions for hair discoloration, process for their preparation and use
EP0697174A1 (en) * 1994-08-17 1996-02-21 HEITLAND UND PETRE INTERNATIONAL GmbH Process for the preparation of antimicrobial agents
US5698186A (en) * 1992-08-17 1997-12-16 Clairol, Inc. Methods of controlling dust and compositions produced thereby

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1449525A (en) * 1974-08-21 1976-09-15 Tokai Electro Chemical Co Method of stabilizing acid aqueous solutions of hydrogen peroxide

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1449525A (en) * 1974-08-21 1976-09-15 Tokai Electro Chemical Co Method of stabilizing acid aqueous solutions of hydrogen peroxide

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0257399A2 (en) * 1986-08-13 1988-03-02 Beratungslabor für die kosmetische und pharmazeutische Industrie Dipl.-Ing. Karlheinz Schrader Hair dyeing composition
EP0257399A3 (en) * 1986-08-13 1988-04-20 Blendax-Werke R. Schneider Gmbh & Co. Hair dyeing composition
US5698186A (en) * 1992-08-17 1997-12-16 Clairol, Inc. Methods of controlling dust and compositions produced thereby
US5447654A (en) * 1993-04-05 1995-09-05 L'oreal Bleaching composition in granulated form which may be used for bleaching hair and process for the preparation of the said composition
FR2703589A1 (en) * 1993-04-05 1994-10-14 Oreal Bleaching composition in granulated form suitable for hair bleaching and process for preparing said composition.
US5650091A (en) * 1993-04-05 1997-07-22 L'oreal Process for the preparation of a granulated bleaching composition comprising first and second binders
EP0619114A1 (en) * 1993-04-05 1994-10-12 L'oreal Bleaching composition in granulate form for hair bleaching and process for preparing it
EP0663205A1 (en) * 1994-01-14 1995-07-19 L'oreal Cosmetic compositions for hair bleaching, process for their synthesis and their use
FR2715065A1 (en) * 1994-01-14 1995-07-21 Oreal Cosmetic compositions for hair discoloration, synthesis method and use.
US5612022A (en) * 1994-01-14 1997-03-18 L'oreal Pulverulent hair bleach of peroxygen oxidizer and polyoxyethylene/polyoxypropylene copolymer
US5622691A (en) * 1994-01-14 1997-04-22 L'oreal Preparing pulverulent hair bleach of peroxygen oxidizer and polyoxyethylene/polyoxypropylene copolymer
FR2716804A1 (en) * 1994-03-02 1995-09-08 Oreal Cosmetic compositions for hair discoloration, process for their preparation and use
EP0672408A1 (en) * 1994-03-02 1995-09-20 L'oreal Cosmetic compositions for hair bleaching, its preparation process and its use
US5660190A (en) * 1994-03-02 1997-08-26 L'oreal Cosmetic compositions for bleaching the hair, preparation, process and use thereof
EP0697174A1 (en) * 1994-08-17 1996-02-21 HEITLAND UND PETRE INTERNATIONAL GmbH Process for the preparation of antimicrobial agents

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