WO2002055648A1 - Gels destines a la liberation ciblee de matieres odoriferantes - Google Patents

Gels destines a la liberation ciblee de matieres odoriferantes Download PDF

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Publication number
WO2002055648A1
WO2002055648A1 PCT/EP2002/000036 EP0200036W WO02055648A1 WO 2002055648 A1 WO2002055648 A1 WO 2002055648A1 EP 0200036 W EP0200036 W EP 0200036W WO 02055648 A1 WO02055648 A1 WO 02055648A1
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WO
WIPO (PCT)
Prior art keywords
fragrance
methyl
acid
composition according
alcohol
Prior art date
Application number
PCT/EP2002/000036
Other languages
German (de)
English (en)
Inventor
Ilona Lange
Thomas Gerke
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to EP02703535A priority Critical patent/EP1352047A1/fr
Publication of WO2002055648A1 publication Critical patent/WO2002055648A1/fr

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Classifications

    • 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
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A61K8/25—Silicon; Compounds thereof
    • 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
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/003—Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
    • 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
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/507—Compounds releasing perfumes by thermal or chemical activation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms

Definitions

  • the invention relates to a fragrance composition
  • a fragrance composition comprising an aqueous gel matrix, a fragrance derivative which slowly releases the fragrance under the influence of protons and a protonic acid.
  • the invention relates to a method for producing these gel-like fragrance compositions and their use as an additive for cleaning agents, cosmetics, deodorants, paints and varnishes, as well as agents for the antimicrobial treatment of fabrics or for keeping insects away from waste collection containers.
  • Fragrance and aroma substances play an increasing role in the field of textile and personal care products.
  • Crucial for the perceptibility of a fragrance is its volatility, whereby in addition to the nature of the functional groups and the structure of the chemical compound, the molar mass also plays an important role.
  • Most odoriferous substances have molecular weights of up to about 200 daltons, while molecular weights of 300 daltons and more are an exception. Due to the different volatility of odoriferous substances, the smell of a perfume or fragrance composed of several odoriferous substances changes during evaporation, the odor impressions being described in "top note”, “heart or middle note” (“middle note”) or “body”) and “base note” (“end note” or “dry out”).
  • the top note of a perfume or fragrance does not consist solely of volatile compounds, while the base note largely consists of less volatile, i.e. non-stick fragrances.
  • the base note largely consists of less volatile, i.e. non-stick fragrances.
  • more volatile fragrances can be bound to certain fixatives, for example, which prevents them from evaporating too quickly.
  • a basic method for the targeted release of fragrances e.g. B. from detergents, is their direct addition to the application formulation.
  • the disadvantage of this method is the immediate release of the fragrance from the formulation, which leads to a short-term fragrance effect and thus the shelf life of the Formulation greatly reduced.
  • Added to this is the low chemical stability to atmospheric oxygen, which has been observed with numerous fragrances, especially with aldehydes and alcohols. Attempts to encapsulate such substances or to include them in cyclodextrins have been unsuccessful or uneconomical due to the high raw material prices. Immobilization by chemical derivatization proved to be more advantageous.
  • WO-A-95/04809 teaches the slow cleavage of fragrance alcohol esters by means of lipases, which produces a long-lasting fragrance.
  • WO-A-97/30687 and EP-A-816322 bind to sulfonates, sulfates and phosphates, with similar effects being achieved.
  • Further possibilities for the targeted slow release of fragrance alcohols are betaine esters, as shown in EP-A-0799885, ⁇ -tertiary carbon esters in WO-A-98/07810, ⁇ -keto esters in WO-A-98/07813 or linear or cyclic acetals.
  • WO-A-94/06441 relates to the acid hydrolysis of acetals and orthoesters, which are based on aldehydes / ketones or alcohols with fragrance properties.
  • EP-A-0820762 describes the loading of silica particles with fragrances and their use in washing powders.
  • EP-A-0281034 teaches the inclusion of fragrance compositions in inorganic polymer matrices.
  • the object of the invention described here is to provide compositions for the targeted and uniform release of fragrances over a longer period of time (“slow release”).
  • the object is achieved according to the invention by using proton-cleavable derivatized fragrances and embedding them in an aqueous gel matrix.
  • the invention relates to a fragrance composition
  • a fragrance composition comprising a
  • the slow release of the fragrances is based on the hydrolytic cleavage of the fragrance derivatives under the action of protons within the acidic gel matrix.
  • the resulting fragrances are released to the gel and must first diffuse through the enveloping gel matrix before they can reach the ambient air. Since both the hydrolysis of the fragrance derivative in the gel and the release of the fragrances thereby formed from the gel into the ambient air are diffusion-controlled, the fragrances are released evenly over a long period of time (“slow release”).
  • Suitable proton-cleavable derivatives of the fragrances are those which release the underlying fragrance in the presence of protonic acids, such as
  • esters (I) are based on esterification products of - olfactory alcohols with reactive mono-, di- and tricarboxylic acids
  • fragrance alcohols There are no restrictions on the choice of derivatizable fragrance alcohols, provided that the alcohols have the necessary fragrance properties.
  • suitable fragrance alcohols are selected from amyl alcohol, 2-hexyl alcohol, hexyl alcohol, heptyl alcohol, octyl alcohol, nonyl alcohol, decyl alcohol, undecyl alcohol, lauryl alcohol, myristic alcohol, 3-methyl-but-2-en-1-ol, 3-methyl-1-pentanol, cis-3-hexenol, cis-4-hexenol, 3,5,5-trimethylhexanol, 3,4,5,6,6-pentamethylheptan-2-ol, citronellol, geraniol, oct-1-en-3-ol, 2,5,7-trimethyl octan-3-ol, 2-cis-3,7-dimethyl-2,6-octadien-1-ol, 6-ethyl-3-methyl-5-octen-1
  • carboxylic acids used to esterify the scented alcohols must not have a strong intrinsic odor that, after hydrolysis, has a negative impact on the odor impression.
  • Mono-, di- and tricarboxylic acids which are suitable in the context of the present invention are, for example, stearic acid, oxalic acid, malonic acid, succinic acid and citric acid.
  • the esterification of the carboxylic acids with the fragrance alcohols can be carried out by the conventional methods known to those skilled in the art.
  • the acetals (II) which can be used according to the invention are those as described in DE-A-19718537 A1 and WO-A-94/06441.
  • Suitable acetals are based on reaction products of
  • aldehydes and / or ketones there are no restrictions per se, provided these have the necessary fragrance properties.
  • suitable compounds are n-undecanal, 2-methylundecanal, n-tridecanal, 2-methyldodecanal, ⁇ -amylcinnamaldehyde, 10-undecenal, 3,7-dimethyl-6-octen-1-al (citronellal), ⁇ -methyl- ⁇ - (p-tet ⁇ f-butylphenyl) propionaldehyde (Lilial ® ), ⁇ -hexylcinnamaldehyde, dihydrojasmon (3-methyl-2-pentyl-2-cyclopent-1-one), carvone, heliotropin, lonon, methylnaphthyl ketone, vanillin, Anisaldehyde, and mixtures thereof.
  • n-undecanal 2-methylundecanal, n-tridecanal, 2-methyldodecanal, ⁇ -amylcinnamaldehyde, 10-undecenal, citronellal and ⁇ -methyl- ⁇ - (p-terf-butylphenyl) propionaldehyde (Lilial ® )
  • suitable hydroxy and polyhydroxy compounds There are also no restrictions with regard to the selection of suitable hydroxy and polyhydroxy compounds.
  • suitable compounds are ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, terf-butanol, glycerol, erythritol, threitol, pentaerythritol, sorbitol, sorbose, tartaric acid, ascorbic acid, glucose, methylglucoside, alkylgycosides and alkylpolyglycosides Structure (i) specified below, preferred polyols are ethylene glycol, propylene glycol, butanetriol, glycerol, erythritol, threitol, pentaerythritol, sorbitol and alkylpolyglycosides of the general structure (i) - (G) X (i) wherein R is a linear, saturated alkyl radical 8 to 22 carbon atoms and (G) x is a glycoside or oligoglycoside residue with
  • Alkyl glycosides of the formula (i) have been known for a long time and can be prepared from sugars and aliphatic primary alcohols with 8 to 22 carbon atoms with acetalization.
  • Preferred sugar components (glycoses) are glucose, but also fructose, mannose, galactose, telose, gulose, allose, old rose, idose, arabinose, xylose, lyxose, ribose and mixtures thereof.
  • R is very particularly preferably an alkyl group having 8 to 14 carbon atoms.
  • Particularly preferred polyhydroxy compounds in the context of the present invention are those having 3 to 6 OH groups, in particular glycerol.
  • the imines (Schiff bases) which can be used according to the invention are based on products of the implementation of
  • Primary amines which can be used within the scope of the invention are methyl or ethyl anthranilate.
  • the imines are produced by conventional methods described in the prior art.
  • esters (I) and acetals (II) are preferred.
  • the aqueous gel matrix is based on gelled (solidified) inorganic or organic gel formers. Gels based on potassium and sodium silicates (water glass), carrageenan, gum arabic, bone glue, gelatin and the like are preferred. Water glass gels are particularly preferred. The production of such gel matrices is known in the prior art.
  • the water content of the gels which can be used according to the invention, in particular of the water glass gel, is between 40 and 98% by weight, preferably between 50 and 95% by weight, based on the total composition.
  • the pH is to be kept in a range from pH 1 to 7, preferably pH 2.5 -5, by adding protonic acids.
  • Suitable protonic acids can be both organic and inorganic acids. When selecting the protonic acids in question, however, it must be ensured that they do not have an intense intrinsic odor that could distort or mask the odor impression of the fragrances.
  • Preferred organic protonic acids are citric acid, oxalic acid, malic acid, succinic acid or malonic acid inorganic protonic acids are hydrochloric acid, sulfuric acid and phosphoric acid.
  • the gel-like fragrance compositions according to the invention are produced by mixing a gel matrix precursor with at least one proton-cleavable fragrance derivative in the presence of an aqueous protonic acid and then allowing the composition to gel.
  • the apparatus, stirrers and mixers described in the prior art can be used for mixing.
  • the mixture described above can be degassed in a suitable container depending on the viscosity, but generally for a short time, for example 15 minutes, under reduced pressure.
  • the fragrance gel between 0.1 to 10% by weight, preferably 0.5 to 8% by weight, particularly preferably up to 6% by weight, of an individual fragrance derivative or mixtures of different fragrance derivatives, based on the overall composition of the fragrance gel, can be used .
  • the fragrance gels according to the invention can additionally contain 0.01 to 10% by weight, preferably up to 5% by weight of dyes and / or 0.05 to 10% by weight, preferably 0.1 up to 8 wt .-% of gel stabilizing compounds, such as Bentonite, can be added.
  • gel stabilizing compounds such as Bentonite
  • the gel-like fragrance composition according to the invention can also contain conventional fragrances in non-derivatized form.
  • Adhesive odorants in particular, which frequently form the base note of the fragrance, can be used in a particular embodiment of the invention without prior chemical derivatization.
  • Adhesive fragrances that can be used as a fragrance in the context of the present invention are, for example, the essential oils such as angelica root oil, anise oil, arnica flower oil, basil oil, bay oil, Champaca flower oil, noble fir oil, noble pine cone oil, elemi oil, eucalyptus oil, fennel oil, spruce needle oil, galbanum oil, geranium oil, ginger grass oil, guaiac wood oil, gurjun balsam oil, helichrysum oil, ho oil, ginger oil, iris oil, kayam oil, kohl oil, camo oil, kassel oil, kass oil, kassel oil, kassel oil, kassel oil, calamus oil, calam oil Kopa ⁇ vabalsam oil, coriander oil, spearmint oil, caraway oil, cumin oil, lavender oil, lemongrass oil, lime oil, mandarin oil, lemon balm oil, musk grape oil, myrrh oil,
  • fragrances can also be used in the context of the present invention as adhesive fragrances or fragrance mixtures, that is to say fragrances.
  • These compounds include the compounds mentioned below and mixtures of these: ambrettolide, ambroxan, ⁇ -amylcinnamaldehyde, anethole, anisaldehyde, anisalcohol, anisole, anthranilic acid methyl ester, acetophenone, benzylacetone, benzaldehyde, benzoic acid ethyl ester, benzophenone, benzyl alcohol, benziatyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl benzyl
  • the proportion of these additional fragrances can be up to 10% by weight, preferably between 0.5 and 8% by weight, based on the overall composition of the fragrance gel.
  • the gels obtained can be used as fragrances in numerous everyday products due to their low toxicity and good biodegradability.
  • the gels according to the invention are added to such products.
  • the gels according to the invention can be used in personal care compositions such as shower gels, hair gels, skin creams and the like. ⁇ . are incorporated or used to improve the smell of water-based paints and varnishes.
  • the gels according to the invention are also suitable for all types of fragrances, such as. B. room scented, vehicle scented, clothes scented, etc. Due to their high transparency and dimensional stability, they can also decorative functions, e.g. in transparent room fragrances with "slow release” properties or fragrance lamps.
  • fragrances with insect repellent properties e.g. Citral and citronellal can be used to permanently keep insects away from textiles or waste collection containers, in particular bio bins.
  • Citronellal In a three-necked flask with a water separator, 308.3 g Citronellal and
  • the smell test was carried out with a panel of 4 people in a direct comparison of the gels spiked with protected Citronellal (Example 1) and unprotected Citronellal (Example 2). The experiments were repeated at weekly intervals. It was found that the smell of the water glass gel from Example 2 (comparative example) was no longer perceived by the testers after only 2 weeks, while the smell of the gel from Example 1 was no longer perceptible until after 7 weeks.

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

Abstract

L'invention concerne des compositions de matières odoriférantes aqueuses sous forme de gels. Elles comprennent une matrice de gel et un dérivé de matière odoriférante, qui libère l'odeur sous l'influence de protons. La présente invention porte également sur un procédé pour réaliser ces compositions de matières odoriférantes sous forme de gels, et sur leur utilisation en tant qu'adjuvants dans des produits de nettoyage, des produits cosmétiques, des désodorisants, des peintures et des vernis.
PCT/EP2002/000036 2001-01-13 2002-01-04 Gels destines a la liberation ciblee de matieres odoriferantes WO2002055648A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP02703535A EP1352047A1 (fr) 2001-01-13 2002-01-04 Gels destines a la liberation ciblee de matieres odoriferantes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2001101336 DE10101336A1 (de) 2001-01-13 2001-01-13 Gele zur gezielten Freisetzung von Duftstoffen
DE10101336.1 2001-01-13

Publications (1)

Publication Number Publication Date
WO2002055648A1 true WO2002055648A1 (fr) 2002-07-18

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ID=7670447

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/000036 WO2002055648A1 (fr) 2001-01-13 2002-01-04 Gels destines a la liberation ciblee de matieres odoriferantes

Country Status (3)

Country Link
EP (1) EP1352047A1 (fr)
DE (1) DE10101336A1 (fr)
WO (1) WO2002055648A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003011805A1 (fr) * 2001-07-30 2003-02-13 Fulltec Ag Insectifuge
EP2353656A3 (fr) * 2002-11-25 2013-02-13 Colgate-Palmolive Company Precurseurs fonctionnels de parfums
US8642663B2 (en) 2002-10-31 2014-02-04 Franz Bencsits Acetals as insect repellant agents
CN113813738A (zh) * 2021-09-28 2021-12-21 安徽华业香料合肥有限公司 一种基于γ-十一内酯的空气净化材料
EP4174158A1 (fr) * 2021-11-02 2023-05-03 The Procter & Gamble Company Compositions d'entretien de tissus d'acide liquide
EP4174159A1 (fr) * 2021-11-02 2023-05-03 The Procter & Gamble Company Compositions d'entretien de tissus d'acide liquide

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008047893A1 (de) 2008-09-16 2010-03-25 Erhard Schumann Gemisch und Verfahren zur Freisetzung von Duftstoffen unter Wärmeeinwirkung
DE102010008290A1 (de) * 2010-02-17 2011-08-18 Azur Fragrances S.A.R.L. Wasserlöslicher Wirkstoffträger
US20170204223A1 (en) * 2016-01-15 2017-07-20 International Flavors & Fragrances Inc. Polyalkoxy-polyimine adducts for use in delayed release of fragrance ingredients

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1501324A (en) * 1975-05-16 1978-02-15 Japan Synthetic Rubber Co Ltd Hydrogel containing synthetic polymers
WO1994006441A1 (fr) * 1992-09-22 1994-03-31 The Mennen Company Composition contenant une fragrance activee par le corps destinee a etre appliquee sur la peau et son procede d'utilisation
WO1997047720A2 (fr) * 1996-06-11 1997-12-18 The Procter & Gamble Company Procede de production d'un additif particulaire de lessive pour conferer un parfum au linge, a proprietes physiques ameliorees
WO1999027069A1 (fr) * 1997-11-26 1999-06-03 The Procter & Gamble Company Pastille de detergent
WO2000000580A1 (fr) * 1998-06-30 2000-01-06 The Procter & Gamble Company Systeme distributeur de compositions pour blanchisserie renfermant des polyalkylene-imines augmentant la fragrance des beta-cetoesters

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1501324A (en) * 1975-05-16 1978-02-15 Japan Synthetic Rubber Co Ltd Hydrogel containing synthetic polymers
WO1994006441A1 (fr) * 1992-09-22 1994-03-31 The Mennen Company Composition contenant une fragrance activee par le corps destinee a etre appliquee sur la peau et son procede d'utilisation
WO1997047720A2 (fr) * 1996-06-11 1997-12-18 The Procter & Gamble Company Procede de production d'un additif particulaire de lessive pour conferer un parfum au linge, a proprietes physiques ameliorees
WO1999027069A1 (fr) * 1997-11-26 1999-06-03 The Procter & Gamble Company Pastille de detergent
WO2000000580A1 (fr) * 1998-06-30 2000-01-06 The Procter & Gamble Company Systeme distributeur de compositions pour blanchisserie renfermant des polyalkylene-imines augmentant la fragrance des beta-cetoesters

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003011805A1 (fr) * 2001-07-30 2003-02-13 Fulltec Ag Insectifuge
US8481063B2 (en) 2001-07-30 2013-07-09 Fulltec Ag Insect repellent
US8642663B2 (en) 2002-10-31 2014-02-04 Franz Bencsits Acetals as insect repellant agents
US8901068B2 (en) 2002-11-25 2014-12-02 Colgate-Palmolive Company Functional fragrance precursor
US8895495B2 (en) 2002-11-25 2014-11-25 Colgate-Palmolive Company Functional fragrance precursor
US8895496B2 (en) 2002-11-25 2014-11-25 Colgate-Palmolive Company Functional fragrance precursor
EP2353656A3 (fr) * 2002-11-25 2013-02-13 Colgate-Palmolive Company Precurseurs fonctionnels de parfums
US8906843B2 (en) 2002-11-25 2014-12-09 Colgate-Palmolive Company Functional fragrance precursor
CN113813738A (zh) * 2021-09-28 2021-12-21 安徽华业香料合肥有限公司 一种基于γ-十一内酯的空气净化材料
EP4174158A1 (fr) * 2021-11-02 2023-05-03 The Procter & Gamble Company Compositions d'entretien de tissus d'acide liquide
EP4174159A1 (fr) * 2021-11-02 2023-05-03 The Procter & Gamble Company Compositions d'entretien de tissus d'acide liquide
WO2023081624A1 (fr) * 2021-11-02 2023-05-11 The Procter & Gamble Company Compositions liquides acides pour l'entretien de textiles
WO2023081625A1 (fr) * 2021-11-02 2023-05-11 The Procter & Gamble Company Compositions liquides acides pour le soin des tissus
US11891585B2 (en) 2021-11-02 2024-02-06 The Procter & Gamble Company Acidic liquid fabric care compositions

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Publication number Publication date
EP1352047A1 (fr) 2003-10-15
DE10101336A1 (de) 2002-07-25

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