EP1549729B1 - Method for the production of a solid fragrance concentrate - Google Patents

Method for the production of a solid fragrance concentrate Download PDF

Info

Publication number
EP1549729B1
EP1549729B1 EP03748123A EP03748123A EP1549729B1 EP 1549729 B1 EP1549729 B1 EP 1549729B1 EP 03748123 A EP03748123 A EP 03748123A EP 03748123 A EP03748123 A EP 03748123A EP 1549729 B1 EP1549729 B1 EP 1549729B1
Authority
EP
European Patent Office
Prior art keywords
solid
fragrance
mixture
fatty alcohol
liquid
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.)
Expired - Lifetime
Application number
EP03748123A
Other languages
German (de)
French (fr)
Other versions
EP1549729B2 (en
EP1549729A1 (en
Inventor
Raymond Heinz
Hans-Jürgen HUPPERT
Katharina Girke
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.)
Bell Flavors and Fragrances Duft und Aroma GmbH
Original Assignee
Bell Flavors and Fragrances Duft und Aroma GmbH
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=32049241&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP1549729(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Bell Flavors and Fragrances Duft und Aroma GmbH filed Critical Bell Flavors and Fragrances Duft und Aroma GmbH
Publication of EP1549729A1 publication Critical patent/EP1549729A1/en
Application granted granted Critical
Publication of EP1549729B1 publication Critical patent/EP1549729B1/en
Publication of EP1549729B2 publication Critical patent/EP1549729B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50Perfumes
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50Perfumes
    • C11D3/502Protected perfumes
    • C11D3/505Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay

Definitions

  • the invention relates to a process for the preparation of a solid fragrance concentrate, which z. B. for perfuming solid soaps, solid washing and rinsing agents in powder, granule, chip or tablet form and other solid household chemical or cosmetic products is advantageously used.
  • fragrances or fragrance mixtures are liquid at normal temperature and often volatile substances whose introduction into solid household chemical or cosmetic products such.
  • solid soaps or in powder, granular, chip or tablet detergent and detergent problems As solid soaps or in powder, granular, chip or tablet detergent and detergent problems.
  • Powdered solid washing and rinsing agents were intensively mixed according to the prior art prior to packaging or before their formation into tablets, chips, etc. with finely sprayed liquid fragrance concentrate.
  • fragrances When the fragrances are sprayed, high losses of substance occur during evaporation due to evaporation.
  • the often volatile and combustible fragrances together with air form explosive gas-air mixtures, which can lead to deflagrations and fires in the production plants.
  • From DE 19735783 A1 is also a high-dose perfume molding with a content of 20 to 50 wt .-% perfume and the balance, d. H. at least 50% carrier material of fatty acid and fatty acid salt known.
  • the support material of at least 50 wt .-% of the total mass of the perfume molding can be up to 50 wt .-% by conventional ingredients of detergents and cleaners, such as. As enzymes, bleaches, foam inhibitors, dyes, pH adjusters, etc. are replaced, these ingredients have only partial carrier material properties.
  • the latter perfume moldings are limited to a perfume uptake of 50 wt .-%.
  • the fatty acids and fatty acid salts used as support materials are only partially biodegradable.
  • French Patent FR-A-2123824 discloses a solid fragrance composition comprising a soap gel, an organic solvent and a fragrance. Such a fragrance is gelatinous and not really firm.
  • the solid fragrance disclosed in US Patent 3,945,950 is also a gelatinous product consisting of a gelling agent, an ether, and a fragrance wherein the proportion of the ether is greater than that of the fragrance.
  • the gel-like consistency makes this type of solid fragrances of the prior art for introducing z. B. in powdery solid detergents and detergents unsuitable.
  • liquid fragrances or fragrance mixtures are dissolved in normal surfactants or surfactants which contain fatty alcohol (s) or a mixture of fatty alcohol (s) with fatty acid (s) and / or fatty alcohol ethoxylate and / or or polyethylene glycol.
  • liquid fragrances By means of the process according to the invention, up to 60% by weight of liquid fragrances can be dissolved in the surfactants or cosurfactants or the surfactant / cosurfactant mixtures and solidified to give a solid perfume concentrate according to the invention.
  • the solid perfume concentrates obtained in the above manner can be prepared by known methods in pastillierter or granulated form, and they can be in this form in the production of solid soaps, powder, granular or tablet detergent and rinse or other solid household chemical or easily admit and precisely dose cosmetic products.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Jellies, Jams, And Syrups (AREA)

Abstract

The invention relates to a method for the production of a solid fragrance concentrate, by absorption of a liquid fragrance or fragrance mixture in a solid or solid mixture, using one or several surfactants and/or co-surfactants, solid at normal temperatures as solid or solid mixture, whereby the liquid fragrance or fragrance mixture is dissolved in the above at a temperature above the solidification temperature of the solid or solid mixture and the solution subsequently solidified by cooling. The solid or solid mixture comprises fatty alcohol(s) or a mixture of fatty alcohol(s) and fatty acid(s) and/or fatty alcohol ethoxylate and/or polyethylene glycol.

Description

Die Erfindung betrifft ein Verfahren zur Herstellung eines festen Riechstoffkonzentrates, welches z. B. zur Parfümierung von festen Seifen, von festen Wasch- und Spülmitteln in Pulver-, Granulat-, Chip- oder Tablettenform und von anderen festen haushaltchemischen oder kosmetischen Produkten vorteilhaft einsetzbar ist.The invention relates to a process for the preparation of a solid fragrance concentrate, which z. B. for perfuming solid soaps, solid washing and rinsing agents in powder, granule, chip or tablet form and other solid household chemical or cosmetic products is advantageously used.

Eine große Zahl von Riechstoffen oder Riechstoffinischungen sind bei Normaltemperatur flüssige und oftmals leicht flüchtige Substanzen, deren Einbringung in feste haushaltchemische oder kosmetische Produkte wie z. B. feste Seifen bzw. in pulver-, granulat-, chip- oder tablettenförmige Wasch- und Spülmittel Probleme bereitet.A large number of fragrances or fragrance mixtures are liquid at normal temperature and often volatile substances whose introduction into solid household chemical or cosmetic products such. As solid soaps or in powder, granular, chip or tablet detergent and detergent problems.

Die bekannten Technologien zur Parfümierung von Festseifen basieren z. B. auf einem intensiven Vermengen der pilierten Rohseife mit flüssigem Riechstoffkonzentrat vor dem Strangpressen und dem Schneiden sowie dem Nachpressen zu einzelnen Seifenstücken. Werden die flüssigen Riechstoffe in größeren Mengen in die pilierte Rohseife eingebracht, wird die Konsistenz der Seife negativ beeinflusst.The known technologies for perfuming of solid soaps based z. B. on an intensive blending the piled raw soap with liquid fragrance concentrate before extruding and cutting and repressing to individual soap bars. If the liquid fragrances are introduced in large quantities into the pilfered raw soap, the consistency of the soap is adversely affected.

Auch ist es nachteilig, dass sich die in dieser Weise in die Festseifen eingebrachten Riechstoffe relativ rasch verflüchtigen, weil der Seifengrundstoff die Riechstoffe nur in geringen Mengen tatsächlich binden kann, so dass nach längerer Lagerung die meisten der in dieser Weise hergestellten Festseifen einen großen Teil des Wohlgeruches eingebüßt haben.It is also disadvantageous that the fragrances introduced into the solid soaps volatilize relatively quickly, because the soap base can actually bind the fragrances only in small amounts, so that after prolonged storage most of the solid soaps produced in this way make up a large part of the solids Have lost their fragrance.

Pulverförmige feste Wasch- und Spülmittel wurden nach dem Stand der Technik vor dem Verpacken bzw. vor ihrer Formung zu Tabletten, Chips usw. mit fein versprühtem flüssigen Riechstoffkonzentrat intensiv vermengt. Bei dem Versprühen der Riechstoffe entstehen durch Verdunsten bereits in der Fertigung hohe Substanzverluste. Außerdem können die oftmals leichtflüchtigen und brennbaren Riechstoffe zusammen mit Luft explosive Gas-Luft-Gemische bilden, wodurch es in den Fertigungsanlagen zu Verpuffungen und Bränden kommen kann.Powdered solid washing and rinsing agents were intensively mixed according to the prior art prior to packaging or before their formation into tablets, chips, etc. with finely sprayed liquid fragrance concentrate. When the fragrances are sprayed, high losses of substance occur during evaporation due to evaporation. In addition, the often volatile and combustible fragrances together with air form explosive gas-air mixtures, which can lead to deflagrations and fires in the production plants.

Um diese Nachteile zu vermeiden, wurde bereits versucht, feste Riechstoffkonzentrate herzustellen, indem z. B. pulverförmige gefällte Kieselsäure oder andere pulverförmige Trägermaterialien, die eine große innere Oberfläche aufweisen, mit den flüssigen Riechstoffen bzw. Riechstoffmischungen benetzt wurden, wodurch der flüssige Riechstoff bzw. die flüssigen Riechstoffmischungen von den pulverförmigen Materialien adsorbiert und an die inneren Oberflächen dieser Materialien gebunden wurden. Diese pulverförmigen Trägermaterialien sind zwar in der Lage, relativ große Anteile von flüssigen Riechstoffen aufzunehmen und zu binden, da sie jedoch im Wasser schlecht löslich sind, stellen sie vor allem für feste Seifen sowie für Wasch- und Spülmittel unerwünschte Ballaststoffe dar, die zu schädlichen Ablagerungen auf dem Wasch- und Spülgut sowie in den Geräten und Leitungen führen, und sie sind deshalb als Trägermaterialien zur Einbringung von Riechstoffen vor allem in feste Seifen sowie in feste Wasch- und Spülmittel ungeeignet. Außerdem ist das Haftvermögen dieser bekannten Stoffe auf Grund ihrer großen inneren Oberflächen zum Teil so groß, dass sich die Riechstoffe beim Wasch- oder Spülvorgang nicht lösen und entfalten können und somit ungenutzt fortgespült werden.To avoid these disadvantages, attempts have been made to produce solid fragrance concentrates by z. As powdered precipitated silica or other powdery carrier materials having a large inner surface were wetted with the liquid fragrances or fragrance mixtures, whereby the liquid fragrance or the liquid fragrance mixtures were adsorbed by the powdery materials and bonded to the inner surfaces of these materials , Although these powdery carrier materials are able to absorb relatively large amounts of liquid fragrances and bind, but since they are sparingly soluble in water, they represent unwanted dietary fiber, especially for solid soaps and for washing and rinsing, which leads to harmful deposits on the washing and ware as well as in the equipment and lines, and they are therefore unsuitable as carrier materials for the introduction of fragrances, especially in solid soaps and solid detergents and detergents. In addition, the adhesion of these known substances due to their large inner surfaces is sometimes so great that the fragrances can not dissolve and unfold during washing or rinsing and thus be washed away unused.

Aus der DE 19735783 A1 ist ferner ein hochdosierter Duftstoff-Formkörper mit einem Gehalt von 20 bis 50 Gew.-% Duftstoff und der Restmenge, d. h. mindestens 50 % Trägermaterial aus Fettsäure und fettsaurem Salz bekannt. Von diesem Anteil des Trägermaterials von mindestens 50 Gew.-% an der Gesamtmasse des Duftstoff-Formkörpers können bis zu 50 Gew.-% durch übliche Inhaltsstoffe von Wasch- und Reinigungsmitteln, wie z. B. Enzyme, Bleichmittel, Schauminhibitoren, Farbstoffe, pH-Stellmittel usw. ersetzt werden, wobei diese Inhaltsstoffe nur teilweise Trägermaterialeigenschaften besitzen.From DE 19735783 A1 is also a high-dose perfume molding with a content of 20 to 50 wt .-% perfume and the balance, d. H. at least 50% carrier material of fatty acid and fatty acid salt known. Of this proportion of the support material of at least 50 wt .-% of the total mass of the perfume molding can be up to 50 wt .-% by conventional ingredients of detergents and cleaners, such as. As enzymes, bleaches, foam inhibitors, dyes, pH adjusters, etc. are replaced, these ingredients have only partial carrier material properties.

Letztgenannte Duftstoff-Formkörper sind auf eine Duftstoffaufnahme von 50 Gew.-% beschränkt. Außerdem sind die als Trägermaterialien verwendeten Fettsäuren und fettsauren Salze nur bedingt biologisch abbaubar.The latter perfume moldings are limited to a perfume uptake of 50 wt .-%. In addition, the fatty acids and fatty acid salts used as support materials are only partially biodegradable.

Aus dem französischen Patent FR-A-2123824 ist eine feste Duftstoffzusammensetzung bekannt, die ein Seifengel, ein organisches Lösungsmittel und einen Duftstoff beinhaltet. Ein solcher Duftstoff ist von gelartiger Konsistenz und nicht wirklich fest.French Patent FR-A-2123824 discloses a solid fragrance composition comprising a soap gel, an organic solvent and a fragrance. Such a fragrance is gelatinous and not really firm.

In ähnlicher Weise handelt es sich bei dem US-Patent 3945950 offenbarten festen Duftstoff ebenfalls um ein gelartiges Produkt, das aus einem Gelbildner, einem Ether und einem Duftstoff besteht, wobei der Anteil des Ethers größer ist als der des Duftstoffes. Die gelartige Konsistenz macht diese Art von festen Duftstoffen des Standes der Technik zum Einbringen z. B. in pulverförmige feste Wasch- und Spülmittel ungeeignet.Similarly, the solid fragrance disclosed in US Patent 3,945,950 is also a gelatinous product consisting of a gelling agent, an ether, and a fragrance wherein the proportion of the ether is greater than that of the fragrance. The gel-like consistency makes this type of solid fragrances of the prior art for introducing z. B. in powdery solid detergents and detergents unsuitable.

Es ist deshalb Aufgabe der Erfindung, ein Verfahren zur Herstellung eines festen Riechstoffkonzentrates durch Aufnahme eines flüssigen Riechstoffes in einem festen Stoff oder einem Feststoffgemisch zu entwickeln, bei welchem der feste Stoff oder das Feststoffgemisch in der Lage ist, den flüssigen Riechstoff bzw. die flüssigen Riechstoffe auch in größeren Mengen aufzunehmen, ohne diese(n) in zu hohem Maße zu binden, und ohne dass der feste Stoff oder das Feststoffgemisch, einen unlöslichen Ballaststoff darstellt.It is therefore an object of the invention to develop a process for the preparation of a solid fragrance concentrate by incorporating a liquid fragrance in a solid or a solid mixture in which the solid or the solid mixture is capable of the liquid fragrance or the liquid fragrances also to take up in large quantities, without binding these too high, and without the solid substance or the solid mixture, an insoluble fiber.

Die Aufgabe wird durch die kennzeichnenden Merkmale des Patentanspruches 1 gelöst. Vorteilhafte Ausführungsformen der Erfindung bilden die Merkmale der Unteransprüche 2 bis 8.The object is solved by the characterizing features of claim 1. Advantageous embodiments of the invention form the features of the subclaims 2 to 8.

Die Erfindung soll im Weiteren anhand von bevorzugten Ausführungsbeispielen näher erläutert werden.The invention will be explained in more detail below with reference to preferred embodiments.

Die meisten Riechstoffe befinden sich bei Normaltemperatur von 20 °C im flüssigen Aggregatzustand. Für den Verbraucher anwendungsbereite Riechstoffe sind in den meisten Fällen Riechstoffgemische aus bis zu 40, in Einzelfällen sogar noch mehr einzelnen Riechstoffkomponenten. Um diese bei Normaltemperatur flüssigen Riechstoffe oder Riechstoffgemische in relativ hohen Konzentrationen und in bequemer Weise in feste Seifen, in Pulver- oder in anderen festen Formen vorliegende Wasch- und Spülmittel oder andere feste haushaltchemische oder kosmetische Produkte einbringen zu können, ohne dass die Qualität der Produkte merklich beeinträchtigt wird oder dass im Fertigungsablauf Nachteile oder Gefahren eintreten, werden die flüssigen Riechstoffe erfindungsgemäß in bei Normaltemperatur festen Tensiden oder Kotensiden gelöst, die Fettalkohol(e) oder ein Gemisch von Fettalkohol(en) mit Fettsäure(n) und/oder Fettalkoholethoxylat und/oder Polyethylenglykol umfassen. Dies geschieht durch Erwärmung des Fettalkohols bzw. der Fettalkohole oder des genannten Stoffgemisches auf Temperaturen, die nur geringfügig oberhalb der Erstarrungspunkte dieser Stoffe liegen, darauf folgendes Einbringen der flüssigen Riechstoffe oder Riechstoffgemische in die verflüssigten Tenside oder Kotenside bzw. Tensid-Kotensid-Gemische und nachfolgendes Abkühlen, wobei sich die Tenside oder Kotenside bzw. das Tensid-Kotensid-Gemisch mit dem darin gelösten mindestens einem Riechstoff unterhalb einer bestimmten Erstarrungstemperatur, die oberhalb der Normaltemperatur von 20 °C liegt, zu einem erfindungsgemäßen festen Riechstoffkonzentrat verfestigen.Most odoriferous substances are in the liquid state at a normal temperature of 20 ° C. For the consumer, ready-to-use fragrances are in most cases perfume mixtures of up to 40, in some cases even more individual fragrance components. In order to introduce these at normal temperature liquid fragrances or fragrance mixtures in relatively high concentrations and conveniently present in solid soaps, in powder or other solid forms detergents and dishwashing or other solid household chemical or cosmetic products, without compromising the quality of the products According to the invention, the liquid fragrances are dissolved in normal surfactants or surfactants which contain fatty alcohol (s) or a mixture of fatty alcohol (s) with fatty acid (s) and / or fatty alcohol ethoxylate and / or or polyethylene glycol. This is done by heating the fatty alcohol or fatty alcohols or the said mixture to temperatures which are only slightly above the solidification points of these substances, then introducing the liquid fragrances or fragrance mixtures in the liquefied surfactants or fumed or surfactant-cosurfactant mixtures and the following Cooling, wherein the surfactants or cosurfactants or the surfactant-cosurfactant mixture having dissolved therein at least one fragrance below solidify a certain solidification temperature, which is above the normal temperature of 20 ° C, to a solid perfume concentrate according to the invention.

Mittels des erfindungsgemäßen Verfahrens lassen sich in den Tensiden oder Kotensiden bzw. den Tensid-Kotensid-Gemischen bis zu 60 Gew.-% flüssige Riechstoffe lösen und zu einem erfindungsgemäßen festen Riechstoffkonzentrat verfestigen.By means of the process according to the invention, up to 60% by weight of liquid fragrances can be dissolved in the surfactants or cosurfactants or the surfactant / cosurfactant mixtures and solidified to give a solid perfume concentrate according to the invention.

In einem speziellen Anwendungsfall wurden in 60 Gew.-% eines verflüssigten Fettalkohols C22, der auf eine Temperatur von wenigen Graden oberhalb des Erstarrungspunktes von 70 °C erhitzt wurde, 40 Gew.-% eines flüssigen Riechstoffgemisches gelöst. Die Fettalkohol-Riechstoff Lösung erstarrte beim Abkühlen bei einer Temperatur unterhalb 54 °C zu dem erfindungsgemäßen festen Riechstofflconzentrat.In a special application, 40% by weight of a liquid fragrance mixture was dissolved in 60% by weight of a liquefied fatty alcohol C22 which had been heated to a temperature of a few degrees above the solidification point of 70 ° C. The fatty alcohol-fragrance solution solidified on cooling at a temperature below 54 ° C to the solid fragrance concentrate according to the invention.

In einem weiteren Anwendungsfall wurden in einem verflüssigten Gemisch aus 30 Gew.-% Fettalkohol C22 und 30 Gew.-% Fettsäure (Stearin), das einen Erstarrungspunkt von 68 °C aufwies, 40 Gew.-% eines flüssigen Riechstoffgemisches gelöst. Die Fettalkohol-Fettsäure-Riechstoff-Lösung erstarrte beim Abkühlen bei einer Temperatur von unterhalb 47 °C zu dem erfindungsgemäßen festen Riechstoffkonzentrat.In another application, 40% by weight of a liquid fragrance mixture was dissolved in a liquefied mixture of 30% by weight of fatty alcohol C22 and 30% by weight of fatty acid (stearin), which had a freezing point of 68 ° C. The fatty alcohol-fatty acid fragrance solution solidified on cooling at a temperature of below 47 ° C to the solid perfume concentrate according to the invention.

In noch einem weiteren Anwendungsfall wurden in einem verflüssigten Gemisch aus 30 Gew.-% Fettalkohol C22 und 30 Gew.-% Polyethylenglykol, das einen Erstarrungspunkt von 60 °C aufwies, bei einer Temperatur von 80 °C 40 Gew.-% Riechstoffe gelöst. Die Fettalkohol-Polyethylenglykol-Riechstoff Lösung erstarrte beim Abkühlen bei einer Temperatur von unterhalb 54 °C zu dem erfindungsgemäßen festen Riechstoffkonzentrat.In yet another application, in a liquefied mixture of 30% by weight of fatty alcohol C22 and 30% by weight of polyethylene glycol, which had a solidification point of 60 ° C., 40% by weight of fragrances were dissolved at a temperature of 80 ° C. The fatty alcohol-polyethylene glycol fragrance solution solidified on cooling at a temperature of below 54 ° C to the solid perfume concentrate according to the invention.

Die in der vorstehenden Weise gewonnenen festen Riechstoffkonzentrate können mittels bekannter Verfahren in pastillierter oder granulierter Form hergestellt werden, und sie lassen sich in dieser Form bei der Herstellung fester Seifen, pulver-, granulat- oder tablettenförmiger Wasch- und Spülmittel bzw. anderer fester haushaltchemischer oder kosmetischer Produkte problemlos zugeben und präzise dosieren.The solid perfume concentrates obtained in the above manner can be prepared by known methods in pastillierter or granulated form, and they can be in this form in the production of solid soaps, powder, granular or tablet detergent and rinse or other solid household chemical or easily admit and precisely dose cosmetic products.

Die beschriebenen Ausführungsbeispiele dienen lediglich zur Erläuterung der Erfindung. Der Schutzumfang der Erfindung wird durch den Wortlaut der anliegenden Patentansprüche bestimmt.The described embodiments are merely illustrative of the invention. The scope of the invention is determined by the language of the appended claims.

Claims (8)

  1. Method for the production of a solid fragrance concentrate by means of the absorption of a liquid fragrance or fragrance mixture in a solid or solid mixture, comprising one or more surfactants and/or co-surfactants that are solid at normal temperature, whereby the liquid fragrance or the fragrance mixture is dissolved in the solid or solid mixture at a temperature that lies above its solidification temperature, and ,then solidified by means of cooling of the solution, characterized in that the solid or the solid mixture is formed by fatty alcohol(s) or a mixture of fatty alcohol(s) with fatty acid(s) and/or fatty alcohol ethoxylate and/or polyethylene glycol.
  2. Method as recited in claim 1, characterized in that 10 to 60 wt.-% of a liquid fragrance or fragrance mixture are dissolved in 90 to 40 wt.-% of a fatty alcohol C22, above its solidification point between 66 and 70°C, and then solidified by cooling the solution to normal temperature.
  3. Method as recited in claim 1, characterized in that 10 to 60 wt.-% of a liquid fragrance or fragrance mixture are dissolved in a mixture of 45 to 20 wt.-% of a fatty alcohol C22 and 45 to 20 wt.-% of a fatty acid, above a solidification point of the fatty alcohol/fatty acid mixture, and then solidified by cooling the solution to normal temperature.
  4. Method as recited in claim 1, characterized in that 10 to 60 wt.-% of a liquid fragrance or fragrance mixture are dissolved in a mixture of 45 to 20 wt.-% of a fatty alcohol C22 and 45 to 20 wt.-% of a fatty alcohol ethoxylate, above a solidification point of the fatty alcohol/fatty alcohol ethoxylate of 55 to 60°C, and then solidified by cooling the solution to normal temperature.
  5. Method as recited in claim 1, characterized in that 10 to 60 wt.-% of a liquid fragrance or fragrance mixture are dissolved in a mixture of 45 to 20 wt.-% of a fatty alcohol C22 and 45 to 20 wt.-% polyethylene glycol, above a solidification point of the fatty alcohol/polyethylene glycol mixture of 55 to 60°C, and then solidified by cooling the solution to normal temperature.
  6. Method as recited in at least one of the preceding claims, characterized in that the fragrance concentrate is solidified in a shaping process.
  7. Method as recited in claim 6, characterized in that the fragrance concentrate is formed into tablets.
  8. Method as recited in claim 6, characterized in that the fragrance concentrate is granulated.
EP03748123.1A 2002-10-11 2003-10-08 Method for the production of a solid fragrance concentrate Expired - Lifetime EP1549729B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10247583A DE10247583C5 (en) 2002-10-11 2002-10-11 Process for the preparation of a solid perfume concentrate
DE10247583 2002-10-11
PCT/EP2003/011109 WO2004035721A1 (en) 2002-10-11 2003-10-08 Method for the production of a solid fragrance concentrate

Publications (3)

Publication Number Publication Date
EP1549729A1 EP1549729A1 (en) 2005-07-06
EP1549729B1 true EP1549729B1 (en) 2007-01-03
EP1549729B2 EP1549729B2 (en) 2014-06-04

Family

ID=32049241

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03748123.1A Expired - Lifetime EP1549729B2 (en) 2002-10-11 2003-10-08 Method for the production of a solid fragrance concentrate

Country Status (9)

Country Link
US (1) US7485610B2 (en)
EP (1) EP1549729B2 (en)
JP (1) JP2006516153A (en)
CN (1) CN1692154B (en)
AT (1) ATE350455T1 (en)
DE (2) DE10247583C5 (en)
EA (1) EA006727B1 (en)
ES (1) ES2280772T5 (en)
WO (1) WO2004035721A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010149966A1 (en) 2009-06-24 2010-12-29 Bell Flavors & Fragrances Duft Und Aroma Gmbh Microparticles and method of making microparticles

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10357676A1 (en) * 2003-12-10 2005-07-21 Henkel Kgaa Duftkomposite
GB2417204A (en) 2004-08-19 2006-02-22 Bell Flavours & Fragrances Ltd Air treatment apparatus
DE102004052929A1 (en) * 2004-10-29 2006-05-04 Bell Flavors & Fragrances Duft Und Aroma Gmbh Process and apparatus for the production of solid fragrance
DE102005025041A1 (en) * 2005-05-30 2006-12-07 Bell Flavors & Fragrances Duft Und Aroma Gmbh Means for use in dishwashers and apparatus for its metered introduction during the rinsing and drying phases
DE102005036415A1 (en) * 2005-07-29 2007-02-01 Bell Flavors & Fragrances Duft Und Aroma Gmbh Method for attaching volatile substance to carrier element, comprises dipping carrier element into melt or spraying
DE102006029092A1 (en) * 2006-06-24 2007-12-27 Bell Flavors & Fragrances Duft Und Aroma Gmbh Process for the aromatization of cellulosic products
JP5465823B2 (en) * 2006-12-13 2014-04-09 ユニ・チャーム株式会社 Functional sheet and absorbent article
DE102007037147A1 (en) * 2007-08-07 2009-02-12 Henkel Ag & Co. Kgaa Fragrance composites with improved fragrance release
US20110243872A1 (en) * 2008-12-30 2011-10-06 Bell Flavors And Fragrances, Inc. Carbohydrate treatment for fragranced articles
US8476219B2 (en) 2009-11-05 2013-07-02 The Procter & Gamble Company Laundry scent additive
CA2682636C (en) * 2009-11-05 2010-06-15 The Procter & Gamble Company Laundry scent additive
CN103249826B (en) 2010-12-23 2015-07-15 西姆莱斯有限公司 Fragrance granules for detergents
US20130065812A1 (en) * 2011-09-14 2013-03-14 Ecolab Usa Inc. Water-dilutable solid concentrate
US20130126634A1 (en) 2011-11-22 2013-05-23 Ecolab Usa Inc. Solid air freshener
CN108384666A (en) 2012-12-20 2018-08-10 宝洁公司 laundry scent additive
CN103405346B (en) * 2013-06-08 2015-04-22 苏州靖羽新材料有限公司 Preparation method of solid perfume
EP3174561A4 (en) 2014-07-30 2019-07-24 GPCP IP Holdings LLC Air freshener dispensers, cartridges therefor, systems, and methods
ES2881435T3 (en) 2015-10-23 2021-11-29 Basf Se Solid solutions of odor and flavoring substances with vinylactam polymers
WO2018030431A1 (en) 2016-08-09 2018-02-15 Takasago International Corporation Solid composition comprising free and encapsulated fragrances
WO2018055115A1 (en) * 2016-09-26 2018-03-29 Henkel Ag & Co. Kgaa Perfume-containing melting bodies which contain highly ethoxylated non-ionic surfactants
EP3534972B1 (en) 2016-11-02 2022-06-22 Dow Global Technologies, LLC Solid non-aqueous gel air odorizer
CN107260128B (en) * 2017-06-13 2020-09-29 江苏金森海默生物技术有限公司 Olfactory disorder detection kit and application thereof
DE102017222992A1 (en) * 2017-12-18 2019-06-19 Henkel Ag & Co. Kgaa Production of fragrance-containing enamel body
CN111286414B (en) * 2019-11-28 2021-04-27 纳爱斯浙江科技有限公司 Clothing fragrance retaining bead and preparation method thereof

Family Cites Families (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE548617C (en) * 1930-10-08 1932-04-19 Hydrierwerke Akt Ges Deutsche Method for fixing fragrances
US2300769A (en) * 1940-03-28 1942-11-03 Palol Perfumed Products Inc Solid perfume
DE1120046B (en) * 1960-06-30 1961-12-21 Spitzner Arzneimittelfabrik G Grindable, free-flowing product made from essential oils, liquid fragrances and flavors and process for its production
GB1169656A (en) * 1967-12-18 1969-11-05 Fumio Enomoto Scented Composition
FR2123824A5 (en) 1971-02-02 1972-09-15 Oreal Solid perfumed soap - contains a soap gel with volatile solvent water and volatile perfume
US3945950A (en) 1974-10-02 1976-03-23 Universal Oil Products Company Solid perfumed compositions of matter
US4017574A (en) * 1975-06-04 1977-04-12 Colgate-Palmolive Company Process for making variegated soap
GB1587122A (en) * 1976-10-29 1981-04-01 Procter & Gamble Ltd Fabric conditioning compositions
PH17340A (en) * 1980-03-11 1984-08-01 Unilever Nv Detergent composition
US4741899A (en) * 1983-06-06 1988-05-03 Bristol-Myers Company Process for arresting the proliferation of organisms that convert axillary secretions to malodorous materials
JPS60182955A (en) * 1984-03-01 1985-09-18 中村物産株式会社 Production of solid perfume
ZA892227B (en) * 1988-03-23 1990-05-30 Union Camp Corp Fragrance carriers for laundry compositions
CA2004270A1 (en) * 1988-12-29 1990-06-29 William R. Michael Perfume microcapsules for use in granular detergent compositions
US5002681A (en) * 1989-03-03 1991-03-26 The Procter & Gamble Company Jumbo particulate fabric softner composition
CA2015737C (en) * 1989-05-11 1995-08-15 Diane Grob Schmidt Coated perfume particles
US5154842A (en) * 1990-02-20 1992-10-13 The Procter & Gamble Company Coated perfume particles
DK0469228T3 (en) * 1990-07-31 1996-09-23 Procter & Gamble Improved perfume carrier and transfer system for washing applications
US5194172A (en) * 1990-09-13 1993-03-16 The Procter & Gamble Company Aerated and freezer bar soap compositions containing sucrose as a mildness aid and a processing aid
US5635164A (en) * 1991-07-03 1997-06-03 The Mennen Company Stick composition with sodium chloride and stearyl alcohol
US5378468A (en) * 1992-09-22 1995-01-03 The Mennen Company Composition containing body activated fragrance for contacting the skin and method of use
TR28670A (en) * 1993-06-02 1996-12-17 Procter & Gamble Perfume release system containing zeolites.
US5506201A (en) * 1994-04-29 1996-04-09 International Flavors & Fragrances Inc. Formulation of a fat surfactant vehicle containing a fragrance
EP0858317A1 (en) * 1995-10-31 1998-08-19 The Procter & Gamble Company Deodorant cosmetic stick composition
DE19710635A1 (en) * 1997-03-14 1998-09-17 Buck Chemie Gmbh Gel-based cleaning block for toilet hygiene with permanent room air scenting
DE19735783A1 (en) * 1997-08-18 1999-02-25 Henkel Kgaa High dosage perfumed moulding useful in laundry detergent or for separate addition to wash
DE19744571A1 (en) * 1997-10-09 1999-04-15 Haarmann & Reimer Gmbh Toilet stones
US6086644A (en) * 1997-10-10 2000-07-11 Takasago International Corporation Scented candle and manufacturing method for same
DE19746780A1 (en) * 1997-10-23 1999-04-29 Henkel Kgaa Production of perfumed moldings especially beads with high bulk density useful in detergent
DE19749760A1 (en) * 1997-11-11 1999-05-12 Henkel Kgaa Multi-phase stick preparation
DE19808757B4 (en) * 1998-03-02 2007-09-20 Henkel Kgaa Fragrance beads in detergent tablets
DE19917692A1 (en) * 1999-04-20 2000-10-26 Henkel Kgaa Beads for use in sachets for imparting fragrance to dry laundry consist of a washing agent ingredient containing perfume oil so as to obviate need for disposal of carrier material
DE19948667A1 (en) * 1999-10-08 2001-04-12 Henkel Kgaa Detergent component with double-controlled fragrance release
US6531444B1 (en) * 2000-11-09 2003-03-11 Salvona, Llc Controlled delivery system for fabric care products
DE10063428A1 (en) * 2000-12-20 2002-07-11 Henkel Kgaa Dispersions of nanoparticulate fragrance-containing composite materials
US20030126788A1 (en) * 2001-11-07 2003-07-10 Colloid Tech. Inc. Storage stable translucent flammable article
US7381697B2 (en) * 2002-04-10 2008-06-03 Ecolab Inc. Fabric softener composition and methods for manufacturing and using

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010149966A1 (en) 2009-06-24 2010-12-29 Bell Flavors & Fragrances Duft Und Aroma Gmbh Microparticles and method of making microparticles

Also Published As

Publication number Publication date
EA006727B1 (en) 2006-04-28
CN1692154A (en) 2005-11-02
US7485610B2 (en) 2009-02-03
ES2280772T3 (en) 2007-09-16
ATE350455T1 (en) 2007-01-15
DE10247583A1 (en) 2004-04-29
DE50306219D1 (en) 2007-02-15
US20050227905A1 (en) 2005-10-13
EP1549729B2 (en) 2014-06-04
CN1692154B (en) 2010-04-28
JP2006516153A (en) 2006-06-22
EP1549729A1 (en) 2005-07-06
DE10247583B4 (en) 2007-08-23
WO2004035721A1 (en) 2004-04-29
ES2280772T5 (en) 2014-09-19
DE10247583C5 (en) 2009-04-30
EA200401487A1 (en) 2005-10-27

Similar Documents

Publication Publication Date Title
EP1549729B1 (en) Method for the production of a solid fragrance concentrate
DE60213471T2 (en) PROCESS FOR THE PRODUCTION OF EXTRUDED DISPENSING SYSTEMS
DE3330113A1 (en) TRANSPARENT SOAP BARS AND METHOD FOR THE PRODUCTION THEREOF
DE3518100A1 (en) FABRIC SOFTENING POWDERED DETERGENT
EP0541608A1 (en) Method of manufacturing granular material with washing and cleaning properties.
DE3036325C2 (en)
DE3141066A1 (en) METHOD FOR INHIBITING GEL FORMATION IN CRUTCHER SLURDS FROM INORGANIC SALTS
DE69826492T2 (en) SYNTHETIC DETERGENT FORMULATIONS
DE3424317A1 (en) Means for toilet cleaning
EP2166920B1 (en) Ironing pad comprising liquid stain treatment composition
CN105874051A (en) Soap bar
CH633579A5 (en) Free-flowing granular detergent and cleaning agent of high bulk density containing a fabric softener
EP0944697B1 (en) Water-free mixtures of surface-active agents
DE4332373A1 (en) Anhydrous detergent mixtures
DE102014014767A1 (en) Foil wrapped medium portion
DE102013007024A1 (en) Pelletized cleaning agent, a process for its preparation and its uses
DE3145627C2 (en)
EP0881279A2 (en) Process for making granules containing cationic surfactant
DE2352393A1 (en) PROCEDURE FOR GRANULATING A DETERGENT COMPOSITION
DE3331995C2 (en)
EP3910049A1 (en) Method for producing a surfactant-containing liquid
WO2004013271A1 (en) Cleaning agent for hard surfaces
JPS58120553A (en) Manufacture of gypsum containing perfume
DE102022214278A1 (en) Solid refill portion of a fabric softener composition
DE1271884B (en) Process for the production of detergent tablets

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20041009

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PT RO SE SI SK TR

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PT RO SE SI SK TR

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20070103

Ref country code: SI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20070103

Ref country code: IE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20070103

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20070103

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

Free format text: NOT ENGLISH

REF Corresponds to:

Ref document number: 50306219

Country of ref document: DE

Date of ref document: 20070215

Kind code of ref document: P

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

Free format text: LANGUAGE OF EP DOCUMENT: GERMAN

REG Reference to a national code

Ref country code: CH

Ref legal event code: NV

Representative=s name: TROESCH SCHEIDEGGER WERNER AG

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20070403

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BG

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20070404

GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)

Effective date: 20070321

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: PT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20070604

ET3 Fr: translation filed ** decision concerning opposition
REG Reference to a national code

Ref country code: IE

Ref legal event code: FD4D

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2280772

Country of ref document: ES

Kind code of ref document: T3

PLBI Opposition filed

Free format text: ORIGINAL CODE: 0009260

26 Opposition filed

Opponent name: HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN

Effective date: 20070913

PLAX Notice of opposition and request to file observation + time limit sent

Free format text: ORIGINAL CODE: EPIDOSNOBS2

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20070103

NLR1 Nl: opposition has been filed with the epo

Opponent name: HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CZ

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20070103

Ref country code: RO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20070103

PLBB Reply of patent proprietor to notice(s) of opposition received

Free format text: ORIGINAL CODE: EPIDOSNOBS3

BERE Be: lapsed

Owner name: BELL FLAVORS & FRAGRANCES DUFT UND AROMA G.M.B.H.

Effective date: 20071031

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20070404

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MC

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20071031

PLAB Opposition data, opponent's data or that of the opponent's representative modified

Free format text: ORIGINAL CODE: 0009299OPPO

R26 Opposition filed (corrected)

Opponent name: HENKEL AG & CO. KGAA

Effective date: 20070913

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20071031

NLR1 Nl: opposition has been filed with the epo

Opponent name: HENKEL AG & CO. KGAA

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: EE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20070103

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CY

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20070103

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20071008

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: HU

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20070704

APAH Appeal reference modified

Free format text: ORIGINAL CODE: EPIDOSCREFNO

APBM Appeal reference recorded

Free format text: ORIGINAL CODE: EPIDOSNREFNO

APBP Date of receipt of notice of appeal recorded

Free format text: ORIGINAL CODE: EPIDOSNNOA2O

APBQ Date of receipt of statement of grounds of appeal recorded

Free format text: ORIGINAL CODE: EPIDOSNNOA3O

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: AT

Payment date: 20101020

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: TR

Payment date: 20080926

Year of fee payment: 6

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20111025

Year of fee payment: 9

APBU Appeal procedure closed

Free format text: ORIGINAL CODE: EPIDOSNNOA9O

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: TR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20091008

PLAY Examination report in opposition despatched + time limit

Free format text: ORIGINAL CODE: EPIDOSNORE2

REG Reference to a national code

Ref country code: NL

Ref legal event code: V1

Effective date: 20130501

REG Reference to a national code

Ref country code: AT

Ref legal event code: MM01

Ref document number: 350455

Country of ref document: AT

Kind code of ref document: T

Effective date: 20121008

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: AT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20121008

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20130501

REG Reference to a national code

Ref country code: DE

Ref legal event code: R082

Ref document number: 50306219

Country of ref document: DE

Representative=s name: HECHT, JAN-DAVID, DIPL.-PHYS. DR. RER. NAT., DE

PUAH Patent maintained in amended form

Free format text: ORIGINAL CODE: 0009272

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: PATENT MAINTAINED AS AMENDED

27A Patent maintained in amended form

Effective date: 20140604

AK Designated contracting states

Kind code of ref document: B2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PT RO SE SI SK TR

REG Reference to a national code

Ref country code: DE

Ref legal event code: R102

Ref document number: 50306219

Country of ref document: DE

REG Reference to a national code

Ref country code: CH

Ref legal event code: AELC

REG Reference to a national code

Ref country code: DE

Ref legal event code: R102

Ref document number: 50306219

Country of ref document: DE

Effective date: 20140604

REG Reference to a national code

Ref country code: ES

Ref legal event code: DC2A

Ref document number: 2280772

Country of ref document: ES

Kind code of ref document: T5

Effective date: 20140919

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 13

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 14

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 15

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 16

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: IT

Payment date: 20201030

Year of fee payment: 18

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20221020

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20221024

Year of fee payment: 20

Ref country code: ES

Payment date: 20221118

Year of fee payment: 20

Ref country code: DE

Payment date: 20221011

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 20221027

Year of fee payment: 20

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20211031

P01 Opt-out of the competence of the unified patent court (upc) registered

Effective date: 20230527

REG Reference to a national code

Ref country code: DE

Ref legal event code: R071

Ref document number: 50306219

Country of ref document: DE

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

REG Reference to a national code

Ref country code: GB

Ref legal event code: PE20

Expiry date: 20231007

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20231102

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20231007

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20231009

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20231007

Ref country code: ES

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20231009