CA2977566A1 - Stable dispersions - Google Patents
Stable dispersions Download PDFInfo
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- CA2977566A1 CA2977566A1 CA2977566A CA2977566A CA2977566A1 CA 2977566 A1 CA2977566 A1 CA 2977566A1 CA 2977566 A CA2977566 A CA 2977566A CA 2977566 A CA2977566 A CA 2977566A CA 2977566 A1 CA2977566 A1 CA 2977566A1
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- 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
- A61K8/11—Encapsulated compositions
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- 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
- A61K8/04—Dispersions; Emulsions
- A61K8/044—Suspensions
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- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
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- 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
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- 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
- C11D17/0017—Multi-phase liquid compositions
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/06—Powder; Flakes; Free-flowing mixtures; Sheets
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/08—Silicates
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/10—Carbonates ; Bicarbonates
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/12—Water-insoluble compounds
- C11D3/124—Silicon containing, e.g. silica, silex, quartz or glass beads
- C11D3/1246—Silicates, e.g. diatomaceous earth
- C11D3/128—Aluminium silicates, e.g. zeolites
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2068—Ethers
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2072—Aldehydes-ketones
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2093—Esters; Carbonates
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
- C11D3/225—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin etherified, e.g. CMC
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/28—Heterocyclic compounds containing nitrogen in the ring
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
- C11D3/502—Protected perfumes
- C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
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- 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
- A61K2800/52—Stabilizers
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- 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
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5422—Polymers characterized by specific structures/properties characterized by the charge nonionic
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- 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
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/548—Associative polymers
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- 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
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- Dispersion Chemistry (AREA)
- Emergency Medicine (AREA)
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- Fats And Perfumes (AREA)
- Colloid Chemistry (AREA)
- Cosmetics (AREA)
Abstract
Description
___________________________________________________________________ FIELD OF THE INVENTION
[0001] The invention concerns the field of cosmetic and detergent preparations and concerns new fragrance dispersions with a high content of perfume oils and encapsulated fragrances that are characterized by particularly high stability.
PRIOR ART
However, a mixture of perfume oil and an aqueous capsule slurry is not stable and separates immediately into water, an oil phase, and capsules. In this case, the use of dispersants or emulsifiers is also only possible to a limited extent, and many capsules release their ingredients (e.g.
fragrances) in a surfactant environment.
In example II, (pp.
45-46), a cleaning/care shampoo is disclosed as a cleaning agent that contains a perfume component I (ordinary perfume oil) and an encapsulated perfume component II, as well as the nonionic polymer xanthan.
) '
however, no capsules or solid particles are dispersed.
2014/064255 A2 (GIVAUDAN). Described is stabilization of the capsules during storage in a medium at a specified pH.
US 4428869 A (MUNTEANU et. al) discloses hydroalcoholic compositions for cosmetic purposes, which e.g. are diluted with aqueous ethanol into a perfume (cologne). In examples III, IV and V, mixtures are described that are in the form of a thixotropic fragrant paste and contain the liquid perfume composition A, the powdered perfume compositions B/D/E and "Klucel EF"
=
hydroxyethylcellulose as a thickener. These pastes are suspended in aqueous ethanol in amounts of 2-95%.
US 2008/118568 Al (SMETS JOHAN et. al.) concerns the encapsulation of active ingredients, more particularly fragrances, for use in various fields such as cleaning agents or cosmetic preparations that contain the nonionic polymer Aculyn 44.
Finally, the subject matter of US 2011/269658 Al (DIHORA JITEN ODHAVJI et.
al.) concerns encapsulated active ingredients. Example 27 describes shampoos (I-III, VII-VIII), which contain both free and encapsulated fragrances and a salt of the compound hydroxypropyl guar. The latter serves as a stabilizer for the shampoo formulation.
1 i W02016/134994 ' by weight of encapsulated fragrances, and are characterized by outstanding storage stability with respect to separation into various phases for at least 6 weeks in the low, medium, and high temperature range. A further performance criterion was that the capsules show sufficient stability in the dispersion of oil, water, capsules and dispersants, i.e. do not release their ingredients in large amounts before they are incorporated into the cosmetic or detergent formulations. The previous addition of dispersants should also not affect the capsules in such a way that they subsequently release their ingredients into the cosmetic and detergent formulations more quickly than they would without said addition of dispersants or emulsifiers.
DESCRIPTION OF THE INVENTION
It is therefore possible to use as fragrances individual odorant compounds, either synthetic or natural compounds of the class of esters, ethers, aldehydes, ketones, alcohols, hydrocarbons, acids, carbonic esters, aromatic hydrocarbons, aliphatic hydrocarbons, saturated and/or unsaturated hydrocarbons, and mixtures thereof.
Suitable fragrance aldehydes and fragrance ketones are commonly known to the person skilled in the art. The fragrance ketones may comprise all ketones which are able to impart a desired fragrance or a sensation of freshness. Mixtures of different ketones may also be used. For example, the ketone may be selected from the group consisting of Buccoxime, isojasmone, methyl B-naphthyl ketone, musk indanone, Tonalid/musk plus, a-damascone, B-damascone, 5-damascone, isodamascone, damascenone, damarose, methyl dihydrojasmonate, menthone, carvone, camphor, fenchone, a-ionone, f3-ionone, dihydro-13-ionone, y-methyl so-called ionone, fleuramone, dihydrojasmone, cisjasmone, Iso-E-Super, methyl cedrenyl ketone or methyl cedrylone, acetophenone, methyl acetophenone, para-methoxyacetophenone, methyl naphthyl ketone, benzylacetone, benzophenone, para-hydroxyphenylbutanone, celery ketone or Livescone, 6-isopropyldecahydro-2-naphthone, dimethyloctenone, Freskomenthe, 4-(1-ethoxyviny1)-3,3,5,5-tetramethyl cyclohexa none, methyl heptenone, 2-(2-(4-methy1-3-cyclohexen-1-yl)propyl)cyclopentanone, 1-(p-menthen-6(2)-yI)-1-propanone, 4-(4-hydroxy-3-methoxypheny1)-2-buta none, 2-acetyl-3,3-dimethyl norbornane, 6,7-dihydro-1,1,2,3,3-pentamethy1-4(5H)-indanone, 4-damascol, dulcinyl or cassione, gelsone, hexalone, isocyclemone E, methyl cyclocitrone, methyl lavender ketone, orivone, para-tert-butylcyclohexanone, verdone, delphone, muscone, neobutenone, plicatone, veloutone, 2,4,4,7-tetramethyloct-6-en-3-one, tetramerane, hedione and mixtures thereof. The ketones may preferably be selected from a-damascone, 5-damascone, isodamascone, carvone, y-methyl ionone, lso-E-Super, 2,4,4,7-tetramethyloct-6-en-3-one, benzyl acetone, 0-damascone, damascenone, methyl dihydrojasmonate, methyl cedrylone, hedione and mixtures thereof.
2,6,10-trimethy1-9-undecenal, 3-dodecen-1-al, a-n-amylcinnamaldehyde, 4-methoxybenzaldehyde, benzaldehyde, 3-(4-tert-butylphenyI)-propanal, 2-methyl-3-(para-methoxyphenylpropanal), 2-methy1-4-(2,6,6-trimethy1-2(1)-cyclohexen-1-yl)butanal, 3-phenyl-2-propenal, cis-/trans-3,7-dimethy1-2,6-octadien-1-al, 3,7-dimethy1-6-octen-1-al, [(3,7-dimethy1-6-octenypoxy]acetaldehyde, 4-isopropylbenzaldehyde, 1,2,3,4,5,6,7,8-octahydro-8,8-dimethy1-2-naphthaldehyde,2,4-dimethy1-3-cyclohexene-1-carboxyaldehyde, 2-methyl-3-(isopropyl phenyl)propanal, decyl aldehyde, 2,6-dimethy1-5-heptenal; 4-(tricyclo[5.2.1.0(2,6)]-decylidene-8)-butanal; octahydro-4,7-methanol H-indene carboxaldehyde; 3-ethoxy-4-hydroxybenzaldehyde, para-ethyl-a,a-dimethylhydrocinnamaldehyde, a-methyl-3,4-(methylene dioxy)-hydrocinnamaldehyde,3,4-methylene dioxybenzaldehyde, a-n-hexylcinnamaldehyde, m-cymene-7-carboxaldehyde, a-methyl phenylacetaldehyde, 7-hydroxy-3,7-dimethyl octanal, undecenal, 2,4,6-trimethy1-3-cyclohexene-1-carboxaldehyde, 4-(3)(4-methyl-3-penteny1)-3-cyclohexene carboxaldehyde, 1-dodecanal, 2,4-dimethylcyclohexene-3-carboxaldehyde, 4-(4-hydroxy-4-methyl penty1)-3-cylohexene-1-carboxaldehyde, 7-methoxy-3,7-dimethyloctan-1-al, 2-methyl undecanal, 2-methyl decanal, 1-nonanal, 1-octanal, 2,6,10-trimethy1-5,9-undecadienal, 2-methy1-3-(4-tertbutyl)propa nal, 3-(4-ethylpheny1)-2,2-dimethylpropanal, 3-(4-methoxyphenyI)-2-methylpropanal, methyl nonylacetaldehyde, 2-phenylpropan-1-al, 3-phenylprop-2-en-1-al, 3-pheny1-2-pentylprop-2-en-1-al, 3-phenyl-2-hexylprop-2-enal, 3-(4-isopropyl pheny1)-2-methylpropan-1-al, 3-(4-ethylphenyI)-2,2-dimethylpropan-1-al, 3-(4-tert-butylphenyl)-2-methyl-3-(3,4-methylendioxy-phenyl)-2-methylpropan-1-al, 3-(4-ethylphenyI)-2,2-dimethylpropanal, 3-(3-isopropyl phenyl)-butan-1-al, 2,6-dimethylhept-5-en-1-al, dihydrocin na ma Idehyde,1-methy1-4-(4-methy1-3-penteny1)-3-cyclohexene-1-carboxaldehyde, 5 or 6 methoxyhexahydro-4,7-methanoindan-1 or 2-carboxyaldehyde, 3,7-dimethyloctan-1-al, 1-undecanal, 10-undecen-1-al, 4-hydroxy-3-methoxybenzaldehyde, 1-methy1-3-(4-methylpenty1)-3-cyclohexene-carboxyaldehyde,7-hydroxy-3,7-dimethyloctanal; trans-4-decenal, 2,6-nonadienal, para-tolylacetaldehyde; 4-methylphenylacetaldehyde, 2-methy1-4-(2,6,6-trimethyl-1-cyclohexen-1-y1)-2-butenal, ortho-methoxycinnamaldehyde, 3,5,6-trimethy1-3-cyclohexene carboxaldehyde, 3,7-dimethy1-2-methylene-6-octenal, phenoxyacetaldehyde; 5,9-dimethy1-4,8-decadienal, peony aldehyde (6,10-dimethy1-3-oxa-5,9-undecadien-1-al), hexahydro-4,7-methanoindan-1-carboxaldehyde, octanal, 2-methyl octanal, a-methy1-4-(1-methylethypbenzene acetaldehyde, 6,6-dimethy1-2-norpinene-2-propionaldehyde, paramethyl phenoxyacetaldehyde, 2-methyl-3-phenyl-2-propen-1-al, 3,5,5-trimethylhexanal, hexahydro-8,8-dimethy1-2-naphthaldehyde, 3-propyl-bicyclo[2.2.1]-hept-5-ene-2-carbaldehyde, 9-decenal, 3-methyl-5-phenyl-1-penta nal, methyl nonyl acetaldehyde,1-p-menthene-q-carboxaldehyde, citral or mixtures thereof, lilial citral, 1-decanal, n-undecanal, n-dodecanal, florhydral, 2,4-di methyl-3-cyclohexene-1-carboxaldehyde 4-methoxybenzaldehyde, 3-methoxy-4-hydroxybenzaldehyde, 3-ethoxy-4-hydroxybenzaldehyde, 3,4-methylene dioxybenzaldehyde, and 3,4-dimethoxybenzaldehyde and mixtures thereof. As mentioned in the above examples, the fragrance aldehydes and fragrance ketones can have an aliphatic, cycloaliphatic, aromatic, ethylenically unsaturated structure or a combination of these structures.
Moreover, there may also be further heteroatoms or polycyclic structures. The structures can have suitable substituents such as hydroxyl or amino groups. For further suitable fragrances selected from aldehydes and ketones, reference is made to "Steffen Arctander, published 1960 and 1969 respectively, reprinted 2000 ISBN: Flavoring Agent Chemicals Vol. 1: 0-931710-37-5, Flavoring Agent Chemicals Vol. 2: 0-931710-38-3."
In order to form a fragrance precursor, a desired fragrance raw material is typically joined chemically to a carrier, preferably a carrier of low or moderate volatility. The combination results in a less volatile and more strongly hydrophobic fragrance precursor, with better attachment to materials. The fragrance is released subsequently by breaking of the bond between the fragrance raw material and the carrier, as a result of the change in pH, for example (through perspiration during wear, for example), atmospheric humidity, heat and/or sunlight during storage or drying on a clothesline.
, , , .
The fragrance raw materials that are useful herein include any pleasant smelling fragrances or mixtures of substances which have already been described above.
The use of such substances, in particular in (preferably water-insoluble) microcapsules, corresponds to a preferred embodiment of the invention.
R¨C(R1)(0R3)-0R2 (IV) where R denotes a linear C1-C20 alkyl, branched C3-C20 acyl, cyclic C6-C20 alkyl, branched cyclic C6-C20 alkyl, linear C2C20 alkenyl, branched C3-C20 alkenyl, cyclic C6-C20 alkenyl, branched cyclic C6-C20 alkenyl, substituted or unsubstituted C6-C20 aryl, and mixtures thereof; R1 is hydrogen or R; R2 and R3, each independently of one another, are selected from the group composed of linear Cl-C20 alkyl, branched C3-C20 alkyl, cyclic C3-C20 alkyl, branched cyclic C6-C20 alkyl, linear C6-C20 alkenyl, branched C6-C20 alkenyl, cyclic C6-C20 alkenyl, branched cyclic C6-C20 alkenyl, C6-C20 aryl, substituted C7-C20 aryl, and mixtures thereof. The use of such substances, in particular in (preferably water-insoluble) microcapsules, corresponds to a preferred embodiment of the invention.
substituted or unsubstituted C6-C40 alkylene aryl; substituted or unsubstituted C6-C32 aryloxy; substituted or unsubstituted C6-C40 alkylene oxyaryl; C6-C40 oxyalkylene aryl; and mixtures thereof. The use of such substances, in particular in (preferably water-insoluble) microcapsules, corresponds to a preferred embodiment of the invention.
The presence of silicic acid ester mixtures often makes it possible to even further improve the fragrance impression obtainable, with respect to both pleasant aroma and intensity. The fragrance impression is not only better from a qualitative standpoint, i.e.
with respect to pleasant aroma, but is also longer-lasting.
W02016/134994 =
aldehyde, and mixtures thereof. The use of such substances, in particular in (preferably water-insoluble) microcapsules, corresponds to a preferred embodiment of the [invention].
These are understood to be spherical aggregates that contain at least one solid or liquid core surrounded by at least one continuous membrane. The fragrances can be encapsulated by coating materials and be present as macrocapsules with diameters of about 0.1 to about 5 mm or microcapsules with diameters of about 0.0001 to about 0.1 mm.
2004 050069 Al.
According to a third method, particles are coated with alternating layers of differently charged polyelectrolytes ("layer-by-layer" method). The microscopically small capsules can be dried in the same way as powders. In addition to single-core microcapsules, there are also multiple-core aggregates, also known as microspheres, which contain two or more cores distributed in the continuous membrane material. In addition, single-core or multiple-core microcapsules may be surrounded by an additional second, third etc. membrane. The membrane may consist of natural, semisynthetic or synthetic materials. Natural membrane materials are, for example, gum arabic, agar, agarose, maltodextrins, alginic acid and salts thereof, for example sodium or calcium alginate, fats and fatty acids, cetyl alcohol, collagen, chitosan, lecithins, gelatin, albumin, shellac, polysaccharides such as starch or dextran, polypeptides, protein hydrolysates, sucrose and waxes.
Examples of semisynthetic membrane materials are chemically modified celluloses, particularly cellulose esters and ethers, such as cellulose acetate, ethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose and carboxymethyl cellulose, and starch derivatives, particularly starch ethers and esters. Synthetic membrane materials are, for example, polymers, such as polyacrylates, polyamides, polyvinyl alcohol or polyvinyl pyrrolidone.
Microcapsules having average diameters in the range of 0.0001 to 5, preferably 0.001 to 0.5 and more particularly 0.005 to 0.1 mm, consisting of an envelope membrane and a matrix comprising the active substances, may be obtained, for example, by (a) preparing a matrix from gel formers, cationic polymers and active substances, ' , (b) optionally dispersing the matrix in an oil phase, and (c) treating the dispersed matrix with aqueous solutions of anionic polymers, and optionally removing the oil phase.
INDUSTRIAL APPLICABILITY
, .
from coco-, palm-, tallow- or leyl alcohol, and an average of 2 to 8 EO per mole of alcohol.
Examples of preferred ethoxylated alcohols include C12_14-alcohols with 3 E0, 4 E0, or 7 EQ. C9_11-alcohols with 7 E0, C13_15-alcohols with 3 E0, 5 E0, 7 E0 or 8 E0, C12-18-alcohols with 3 EO, 5 E0 or 7 E0 and mixtures thereof, such as mixtures of C12-14-alcohols with 3 EO
and C12-18-alcohols with 5 EQ. The cited degrees of ethoxylation constitute statistical average values that can be a whole or a fractional number for a specific product. Preferred alcohol ethoxylates have a narrowed homolog distribution (narrow range ethoxylates, NRE). In addition to these nonionic surfactants, fatty alcohols with more than 12 E0 can also be used. Examples of these are tallow fatty alcohol with 14 E0, 25 E0, 30 EO or 40 E0. Nonionic surfactants that contain EO and PO
groups together in the molecule may also be used according to the invention.
Block copolymers having EO-P0 block units or P0-E0 block units, but also E0-P0-E0 copolymers or copolymers, can be used in this context. Also usable, of course, are mixed alkoxylated nonionic surfactants in which EO and PO units are distributed statistically rather than in block fashion.
Such products are obtainable by the simultaneous action of ethylene oxide and propylene oxide on fatty alcohols.
Suitable surfactants of the sulfonate type are preferably C9_3-alkylbenzene sulfonates, olefin sulfonates, i.e. mixtures of alkene- and hydroxyalkane sulfonates, and disulfonates, as are obtained, for example, from C12-18-monoolefins having a terminal or internal double bond, by sulfonation with gaseous sulfur trioxide and subsequent alkaline or acidic hydrolysis of the sulfonation products. Alkane sulfonates obtained from C12-8 alkanes by sulfochlorination or sulfoxidation, for example, with subsequent hydrolysis or neutralization, are also suitable. The esters of a-sulfofatty acids (ester sulfonates), e.g. the a-sulfonated methyl esters of hydrogenated coco, palm nut or tallow acids, are also suitable.
sarcosinate.
units are also suitable.
Because of their high foaming behavior, they are used in cleaning agents only in relatively small amounts, for example in amounts of 1 to 5% by weight.
Particularly preferred sulfosuccinates contain a fatty alcohol residue derived from ethoxylated fatty alcohols that, considered per se, represent nonionic surfactants (see description below).
Sulfosuccinates whose fatty alcohol residues derive from ethoxylated fatty alcohols having a restricted homolog distribution are particularly preferred. It is likewise also possible to use alk(en)ylsuccinic acid preferably having 8 to 18 carbon atoms in the alk(en)yl chain or salts thereof.
surfactants have good wetting properties and are low foaming, so they are suitable in particular for use in machine washing or cleaning methods.
by weight relative to the total content of the liquid detergents and cleaning agents.
However, particularly good builder properties may even be achieved where the silicate particles produce indistinct or even sharp diffraction maxima in electron diffraction experiments. This is to be interpreted to mean that the products have microcrystalline regions between 10 and a few hundred nm in size, with values of up to at most 50 nm and especially up to at most 20 nm being preferred. This type of so-called X-ray amorphous silicates similarly possess a delayed dissolution in comparison with conventional water glasses. Compacted/densified amorphous silicates, compounded amorphous silicates and overdried X-ray-amorphous silicates are particularly preferred.
and/or P. Zeolite MAPTM (commercial product of the Crosfield company), is particularly preferred as the zeolite P. However, zeolite X and mixtures of A, X and/or P are also suitable. Commercially available and preferred in the context of the present invention is, for example, also a co-crystallizate of zeolite X and zeolite A (approx. 80% by weight of zeolite X), which is marketed by SASOL under the brand name VEGOBOND AX and which can be described by the formula . , . .
nNa20*(1¨n)K20*A1203.(2-2.5)*Si02.(3.5-5.5)*H20 The zeolite can be used as a spray-dried powder or also as a non-dried, still moist from its manufacture, stabilized suspension. In the event the zeolite is used as a suspension, it can contain small additions of nonionic surfactants as stabilizers, for example 1 to 3% by weight, relative to the zeolite, of ethoxylated C12-C13 fatty alcohols having 2 to 5 ethylene oxide groups, C12-C14 fatty alcohols having 4 to 5 ethylene oxide groups, or ethoxylated isotridecanols.
Suitable zeolites exhibit an average particle size of less than 10 pm (volume distribution;
measurement method:
Coulter counter), and preferably contain 18 to 22% by weight, in particular 20 to 22% by weight, of bound water.
detector. The measurement was performed against an external polyacrylic acid standard, which yields realistic molecular weight values because of its structural relationship to the polymers investigated. These data deviate significantly from the molecular weight data in which polystyrene sulfonic acids are used as the standard. The molecular weights measured against polystyrene sulfonic acids are usually much higher than the molecular weights given in the present document.
Copolymers of acrylic acid with maleic acid that contain 50 to 90% by weight of acrylic acid and 50 to 10% by weight of maleic acid have proven particularly suitable. Their relative molecular weight, relative to free acids, is generally 2000 to 70,000 g/mol, preferably 20,000 to 50,000 g/mol, and in particular 30,000 to 40,000 g/mol.
. .
Particularly preferred are polyaspartic acids or their salts and derivatives, which have not only co-builder properties but also a bleach-stabilizing action.
between 20 and 37 as well as so-called yellow dextrins and white dextrins with higher molecular weights in the range of 2,000 g/mol to 30,000 g/mol can also be used.
9,419,091 Bl. The oxidized derivatives of such dextrins are their reaction products with oxidizing agents that are capable of oxidizing at least one alcohol functional group of the saccharide ring to the carboxylic acid functional group. Such oxidized dextrins and methods of synthesizing same are known from the European Patent Applications EP 032202 A, EP 0427349 A, EP 0472042 A and and the International Patent Applications WO 1992/018542 A, WO 1993/008251 A, WO
1994/028030 A, WO 1995/007303 A, WO 1995/012619 A and WO 1995/020608 A, for example.
A product oxidized on C6 of the saccharide ring may be especially advantageous.
. .
. .
patents US 4,524,009, US
4,639,325, European Patent Application EP-A-0150 930 A and Japanese Patent Application JP-A-93/339 896 A, for example, are also preferred.
1995/020029 A.
Suitable aminoalkanephosphonates are preferably ethylenediamine tetramethylenephosphonate (EDTMP), diethylenetriamine pentamethylenephosphonate (DTPMP), and their higher homologs. They are preferably used in the form of the neutrally reacting sodium salts, e.g., as the hexasodium salt of EDTMP or as the hepta- and octasodium salt of DTPMP. Of the class of phosphonates, HEDP is preferably used as a builder. The aminoalkanephosphonates furthermore possess a pronounced heavy-metal binding capability. It may accordingly be preferred, especially when the detergents and cleaning agents also contain bleaches, to use aminoalkanephosphonates, in particular DTPMP, or mixtures of the aforementioned phosphonates to produce said agents.
and below, bleach activators can be incorporated into the detergents and cleaning agents.
Compounds which, under perhydrolysis conditions, yield aliphatic peroxycarboxylic acids having preferably 1 to 10 carbon atoms, more particularly 2 to 4 carbon atoms, and/or optionally substituted perbenzoic acid, can be used as bleach activators. Substances that carry 0-and/or N-acyl groups having the aforementioned number of carbon atoms, and/or optionally substituted benzoyl groups, are suitable. Polyacylated alkylenediamines, more particularly tetraacetyl ethylenediamine (TAED), acylated triazine derivatives, more particularly 1,5-diacety1-2,4-dioxyhexahydro-1,3,5-triazine (DADHT), acylated glycolurils, more particularly tetraacetyl glycoluril (TAGU), N-acylimides, more particularly N-nonanoyl succinimide (NOSI), acylated phenol sulfonates, more particularly n-nonanoyl or isononanoyl oxybenzene sulfonate (n- and iso-NOBS), carboxylic acid anhydrides, more particularly phthalic acid anhydride, acylated polyvalent alcohols, more particularly triacetin, ethylene glycol diacetate, and 2,5-diacetoxy-2,5-dihydrofuran are preferred. In addition to or instead of the conventional bleach activators, so-called bleach catalysts can also be incorporated into the textile processing agent. These substances are bleach-enhancing transition metal salts or transition metal complexes such as Mn, Fe, Co, Ru, or Mo salt complexes or carbonyl complexes. Mn, Fe, Co, Ru, Mo, Ti, V, and Cu complexes having nitrogen-containing tripod ligands, as well as Co, Fe, Cu, and Ru ammine complexes, are also usable as bleach catalysts.
25035-69-2), or of butyl acrylate and methyl methacrylate (CAS 25852-37-3), and which are obtainable, for example, from Rohm & Haas under the trade names Aculyn and Acusol , and from Degussa (Goldschmidt) under the trade name Tego Polymer, e.g. the anionic nonassociative polymers Aculyn 22, Aculyn 28, Aculyn 33 (crosslinked), Acusol 810, Acusol 820, Acusol 823, and Acusol 830 (CAS 25852-37-3); (ii) crosslinked high-molecular-weight acrylic acid copolymers, included among which are, for example, the copolymers, crosslinked with an allyl ether of sucrose or of pentaerythritol, of C10-30 alkyl acrylates with one or more monomers from the group of acrylic acid, methacrylic acid, and their simple esters formed preferably with C1-4 alkanols (INCI: Acrylates/Cio-30 Alkyl Acrylate Crosspolymer), and which are obtainable, for example, from B.F. Goodrich under the trade name Carbopol , e.g. the hydrophobized Carbopol ETD 2623 and Carbopol 1382 (INCI: Acrylates/C10_30 Alkyl Acrylate Crosspolymer), and Carbopol Aqua 30 (formerly Carbopol EX 473).
The structure of the subgroups is made up of glucose, mannose, glucuronic acid, acetate, and pyruvate; the number of pyruvate units determines the viscosity of the xanthan gum. More particularly, a fatty alcohol is also suitable as a thickening agent. Fatty alcohols may be branched or unbranched and of natural or petrochemical origin. Preferred fatty alcohols have a carbon chain length of 10 to 20 carbon atoms, preferably 12 to 18. Mixtures of different carbon chain lengths, such as tallow fatty alcohol or coconut fatty alcohol, are preferably used. Examples are Lorolà Spezia! (C12-14-ROH) or Lorol Technisch (C12-18-ROH) (both from Cognis). Preferred liquid detergents and cleaning agents contain 0.01 to 3% by weight and preferably 0.1 to 1% by weight of the thickener based on the total amount of the agent. The amount of the thickener used depends on the type of thickener and the desired degree of thickening.
Suitable enzymes are, in particular, those in the classes of hydrolases, such as proteases, esterases, lipases or lipolytically active enzymes, amylases, cellu lases or other glycosyl hydrolases, hemicellulase, cutinases,13-glucanases, oxidases, peroxidases, perhydrolases, oxidoreductases, and/or laccases and mixtures of the aforementioned enzymes. All these hydrolases contribute in the wash to the removal of stains such as protein-, grease-, or starch-containing stains and graying. Moreover, cellulases and other glycosyl hydrolases contribute to color retention and to enhanced textile softness by removing pilling and microfibrils. Oxidoreductases can also be used for bleaching and to inhibit color transfer. Enzymatic active substances obtained from bacterial strains or fungi, such as Bacillus subtilis, Bacillus licheniformis, Streptomyces griseus, and Humicola insolens, are particularly suitable. Proteases of the subtilisin type, and more particularly proteases obtained from Bacillus lentus, are preferably used. Enzyme mixtures, for example of protease and amylase or protease and lipase or lipolytically active enzymes, or protease and cellulase, or of cellulase and lipase or lipolytically active enzymes, or of protease, amylase, and lipase or lipolytically active enzymes, or protease, lipase or lipolytically active enzymes and cellulase, but in particular protease- and/or lipase-containing mixtures or mixtures with lipolytically active enzymes, are of particular interest in this context. Examples of such lipolytically active enzymes are the known cutinases. Peroxidases or oxidases have also proven suitable in certain cases.
The suitable amylases include, in particular, a-amylases, isoamylases, pullulanases, and pectinases.
Cellobiohydrolases, endoglucanases, and B-glucosidases, which are also called cellobiases, and mixtures thereof, are preferably used as cellulases. Because different types of cellulase differ in terms of their CMCase and avicelase activities, the desired activities can be adjusted by means of controlled mixtures of the cellulases.
preferred anions are the phosphates and sulfates. From a production engineering standpoint, the use of NaCI or MgC12 in the detergents and cleaning agents is preferred. The proportion of electrolytes in the detergents and cleaning agents is usually 0.1 to 5% by weight.
Nonaqueous solvents can be used in the liquid detergents and cleaning agents in amounts between 0.5 and 15% by weight, but preferably below 12% by weight and in particular below 9%
by weight.
Water-soluble polyamides containing acid groups are also suitable for this purpose. In addition, soluble starch preparations and starch products other than those mentioned above may also be used, e.g., degraded starch, aldehyde starches, etc. Polyvinylpyrrolidone may also be used.
However, cellulose ethers such as carboxymethylcellulose (sodium salt), methylcellulose, hydroxyalkylcellulose and mixed ethers such as methylhydroxyethylcellulose, methylhydroxypropylcellulose, methylcarboxymethylcellulose and mixtures thereof as well as polyvinylpyrrolidone are preferred, e.g., in amounts of 0.1% by weight to 5%
by weight, based on the agent.
, .
. .
range of up to 7. Preservatives based on organic acids and/or the salts thereof are particularly suitable for preservation of the skin-friendly detergents and cleaning agents according to the invention.
Lauryl (or stearyl) dimethyl benzyl ammonium chlorides are suitable antistatics for textile fabrics or as additives to detergents and cleaning agents, resulting in an additional softening effect.
absorbers that are absorbed onto the surface of the treated textiles and improve the light-fastness of the fibers.
Compounds that exhibit these desired properties are, for example, the compounds that act by radiationless deactivation, and derivatives of benzophenone having substituents in the 2- and/or 4-position. Also suitable are substituted benzotriazoles, acrylates phenyl-substituted in the 3-position (cinnamic acid derivatives) optionally having cyano groups in the 2-position, salicylates, organic Ni complexes, and natural substances such as umbelliferone and endogenous urocanic acid.
Typical examples of anionic surfactants are soaps, alkyl benzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, a-methyl ester sulfonates, sulfofatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and the salts thereof, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, N-acylamino acids such as acyl lactylates, acyl tartrates, acyl glutamates, and acyl aspartates, alkyl oligoglucoside sulfates, protein fatty acid condensation products (in particular wheat-based plant products) and alkyl (ether) phosphates. If the anionic surfactants contain polyglycol ether chains, these may exhibit a conventional, but preferably a narrowed homolog distribution. Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkyl . .
. .
phenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers or mixed formals, optionally partially oxidized alk(en)yl oligoglycosides or glucuronic acid derivatives, fatty acid N-alkyl glucamides, protein hydrolysates (in particular wheat-based plant products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, these may exhibit a conventional, but preferably a narrowed homolog distribution. Typical examples of cationic surfactants are quaternary ammonium compounds such as dimethyl distearylammonium chloride, and esterquats, in particular quaternized fatty acid trialkanolamine ester salts. Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkylamidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The above-mentioned surfactants are exclusively known compounds. Typical examples of particularly suitable mild surfactants, i.e. particularly gentle to the skin, are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono-and/or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid glutamates, a-olefin sulfonates, ether carboxylic acids, alkyl oligoglucosides, fatty acid glucamides, alkyl amidobetaines, amphoacetals and/or protein fatty acid condensates, the latter preferably based on wheat proteins.
FinsoIv* TN), linear or branched, symmetrical or asymmetrical dialkyl ethers with 6 to 22 carbon atoms per alkyl group such as dicaprylyl ether (Cetior OE), ring-opening products of epoxidized fatty acid esters with polyols, silicone oils (cyclomethicones, silicone methicone types, etc.) and/or aliphatic or naphthenic hydrocarbons such as squalane, squalene, or dialkyl cyclohexanes.
= addition products of 2 to 30 mol of ethylene oxide and/or 0 to 5 mol of propylene oxide onto linear fatty alcohols with 8 to 22 carbon atoms, fatty acids with 12 to 22 carbon atoms, alkyl phenols with 8 to 15 carbon atoms in the alkyl group, as well as alkylamine with 8 to 22 carbon atoms in the alkyl radical;
= alkyl and/or alkenyl oligoglycosides with 8 to 22 carbon atoms in the alk(en)yl radical and ethoxylated analogs thereof;
= addition products of 1 to 15 mol of ethylene oxide onto castor oil and/or hardened castor oil;
= addition products of 15 to 60 mol of ethylene oxide onto castor oil and/or hardened castor oil;
= partial esters of glycerol and/or sorbitan with unsaturated, linear or saturated, branched fatty acids having 12 to 22 carbon atoms and/or hydroxycarboxylic acids having 3 to 18 carbon atoms, and adducts thereof with 1 to 30 mol of ethylene oxide;
= partial esters of polyglycerol (average degree of self-condensation 2 to 8), polyethylene glycol (molecular weight 400 to 5000), trimethylolpropane, pentaerythritol, sugar alcohols (e.g.
sorbitol), alkyl glucosides (e.g. methyl glucoside, butyl glucoside, lauryl glucoside), and polyglucosides (e.g. cellulose) with saturated and/or unsaturated, linear or branched fatty acids having 12 to 22 carbon atoms and/or hydroxycarboxylic acids having 3 to 18 carbon atoms, and adducts thereof with 1 to 30 mol of ethylene oxide;
= mixed esters of pentaerythritoi, fatty acids, citric acid and fatty alcohols and/or mixed esters of fatty acids having 6 to 22 carbon atoms, methylglucose and polyols, preferably glycerol or polyglycerol, = mono-, di- and trialkyl phosphates, and mono-, di- and/or tri-PEG alkyl phosphates and salts thereof;
. .
. .
= wool wax alcohols;
= polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives;
= block copolymers, e.g. polyethylene glycol-30 dipolyhydroxystearates;
= polymer emulsifiers, e.g. Pemulen* grades (TR-1, TR-2) from Goodrich or Cosmedie SP from Cognis;
= polyalkylene glycols and = glycerol carbonate.
These are homologous mixtures whose average degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and/or propylene oxide and substrates with which the addition reaction is carried out. Civis fatty acid mono- and diesters of addition products of ethylene oxide to glycerol are known as refatting agents for cosmetic preparations.
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Particularly preferred a mpholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C12/18-acylsarcosine. Finally, cationic surfactants may also be considered as emulsifiers, with those of the esterquat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
The term lecithins is understood by the person skilled in the art as meaning those glycerophospholipids which form from fatty acids, glycerol, phosphoric acid and choline by esterification.
Lecithins are thus frequently also referred to as phosphatidylcholines (PC). Examples of natural lecithins which may be mentioned are the cephalins, which are also referred to as phosphatidic acids and represent derivatives of 1,2-diacyl-sn-glycerol-3-phosphoric acids. By contrast, phospholipids are usually understood as meaning mono- and, preferably, diesters of phosphoric acid with glycerol (glycerophosphates), which are generally considered to be fats. In addition, sphingosines and sphingolipids are also suitable.
GRAS 3748), menthol ethylene glycol carbonate (FEMA GRAS 3805), menthol propylene glycol carbonate (FEMA GRAS 3806), menthyl-N-ethyloxamate, monomethyl succinate (FEMA
GRAS
3810), monomenthyl glutamate (FEMA GRAS 4006), menthoxy-1,2-propanediol (FEMA
GRAS
3784), menthoxy-2-methyl-1,2-propanediol (FEMA GRAS 3849) and the menthane carboxylic acid esters and amides WS-3, WS-4, WS-5, WS-12, WS-14 and WS-30 and mixtures thereof.
GRAS 3810). Both the succinate and also the analogue monomenthyl glutarate (FEMA GRAS
4006) are important representatives of monomenthyl esters on the basis of di-and poly-carboxylic acids:
rAN., OW'OH
. 0 :
- 0 _ ,,,......., õ...........õ
3805=Frescolat MGC), menthol propylene glycol carbonate (FEMA GRAS 3784=Frescolate MPC), menthol 2-methyl-1,2-propanediol carbonate (FEMA GRAS 3849) or the corresponding sugar derivatives.
The menthol compounds menthyl lactate (FEMA GRAS 3748=Frescolate ML) and, particularly, menthone glyceryl acetal (FEMA GRAS 3807) or, respectively, menthone glyceryl ketal (FEMA
GRAS 3808), which is marketed under the trade name Frescolat MAG, are also preferred. Among these substances, menthone glyceryl acetal/ketal, menthyl lactate, and menthol ethylene glycol carbonate or menthol propylene glycol carbonate, which are marketed by the applicant under the names Frescolate MGA, Frescolat ML, Frescolat MGC, and Frescolate M PC, have been found to be most particularly advantageous.
1FEMA stands for "Flavor and Extracts Manufacturers Association" and GRAS is defined as "Generally Regarded As Safe". A FEMA GRAS designation means that the substance designated such has been tested according to standard methods and is considered to be toxicologically safe.
Keltrol grades from Kelco; Sepigel grades from Seppic; Salcare grades from Allied Colloids), polyacrylamides, polymers, polyvinyl alcohol and polyvinyl pyrrolidone. Other bodying agents which have proved to be particularly effective are bentonites, for example Bentone Gel VS-5PC
(Rheox) which is a mixture of cyclopentasiloxane, Disteardimonium Hectorite and propylene carbonate. Other suitable bodying agents are surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols, for example pentaerythritol or trimethylol propane, narrow-range fatty alcohol ethoxylates or alkyl oligoglucosides and electrolytes such as sodium chloride and ammonium chloride.
400 , cationic starch, copolymers of diallyl ammonium salts and acrylamides, quaternized vinyl pyrrolidone/vinyl imidazole polymers such as Luviquae(BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides such as Lauryldimonium hydroxypropyl hydrolyzed Collagen (LamequaeL, GriThau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers such as amodimethicone, copolymers of adipic acid and dimethylaminohydroxypropyl diethylenetriamine (Cartaretine, Sandoz), copolymers of acrylic acid with dimethyl diallyl ammonium chloride (Merquat 550, Chemviron), polyaminopolyamides and crosslinked water-soluble polymers thereof, cationic chitin derivatives such as quaternized chitosan, optionally in microcrystalline distribution, condensation products of dihaloalkyls, for example dibromobutane, with bis-dialkylamines, for example bis-dimethylamino-1,3-propane, cationic guar gum such as Jaguar CBS, Jaguar C-17, Jaguar C-16 from Celanese, quaternized ammonium salt polymers such as Mirapol A-15, Mirapor AD-1, Mirapol AZ-1 from Miranol.
protection factors are usually present in amounts of 0.1 to 5 and, preferably, 0.2 to 1% by weight.
UV-B filters can be oil-soluble or water-soluble. The following are examples of oil-soluble substances:
= 3-benzylidene camphor or 3-benzylidene norcamphor and derivatives thereof, for example 3-(4-methylbenzylidene)-camphor;
= 4-aminobenzoic acid derivatives, preferably 4-(dimethylamino)-benzoic acid-2-ethylhexyl ester, 4-(dimethylamino)-benzoic acid-2-octyl ester and 4-(dimethylamino)-benzoic acid amyl ester;
. CA 02977566 2017-08-23 .
, .
= esters of cinnamic acid, preferably 4-methoxycinnamic acid-2-ethylhexyl ester, 4-methoxycinnamic acid propyl ester, 4-methoxycinnamic acid isoamyl ester, 2-cyano-3,3-phenylcinnamic acid-2-ethylhexyl ester (octocrylene);
= esters of salicylic acid, preferably salicylic acid-2-ethylhexyl ester, salicylic acid-4-isopropylbenzyl ester, salicylic acid homomethyl ester;
= derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
= esters of benzalmalonic acid, preferably 4-methoxybenzalmalonic acid di-2-ethylhexyl ester;
= triazine derivatives such as 2,4,6-trianilino-(p-carbo-2'-ethyl-1'-hexyloxy)-1,3,5-triazine and octyl triazone, or dioctyl butamido triazone (Uvasorb HEB);
= propane-1,3-diones such as 1-(4-tert-butylphenyI)-3-(4'-methoxypheny1)-propane-1,3-dione;
= ketotricyclo(5.2.1.0)decane derivatives.
= 2-phenylbenzimidazole-5-sulfonic acid and alkali metal, alkaline earth metal, ammonium, alkylammonium, alkanolammonium and glucammonium salts thereof;
= 1H-benzimidazole-4,6-disulfonic acid, 2,2'-(1,4-phenylene)bis-, disodium salt (Neo Heliopan AP) = sulfonic acid derivatives of benzophenones, preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and salts thereof;
= sulfonic acid derivatives of 3-benzylidene camphor such as 4-(2-oxo-3-bornylidenemethyl)-benzene sulfonic acid and 2-methyl-5-(2-oxo-3-bornylidene)-sulfonic acid and salts thereof.
Plus), 1-phenyl-3-(4'-isopropylpheny1)-propane-1,3-dione and enamine compounds. The UV-A
and UV-B filters may of course also be used in the form of mixtures.
Particularly favorable combinations consist of the derivatives of benzoyl methane, for example 4-tert-buty1-4'-methoxydibenzoylmethane (Parsol 1789) and 2-cyano-3,3-phenylcinnamic acid-2-ethyl hexyl ester (Octocrylene) in combination with esters of cinnamic acid, preferably 4-methoxycinnamic acid-2-ethyl hexyl ester and/or 4-methoxycinnamic acid propyl ester and/or 4-methoxycinnamic acid isoamyl ester. Combinations such as these are advantageously combined with water-soluble filters such as 2-phenylbenzimidazole-5-sulfonic acid and alkali metal, alkaline earth metal, ammonium, alkylammonium, alkanolammonium and glucammonium salts thereof.
finely dispersed metal oxides or salts, may also be used for this purpose.
Examples of suitable metal oxides are, in particular, zinc oxide and titanium dioxide and also oxides of iron, zirconium oxide, silicon, manganese, aluminium and cerium and mixtures thereof.
Silicates (talcum), barium sulfate and zinc stearate may be used as salts. The oxides and salts are used in the form of the pigments for skin-care and skin-protecting emulsions and decorative cosmetics.
The particles should have a mean diameter of less than 100 nm, preferably between 5 and 50 nm and more preferably between 15 and 30 nm. They may be spherical in shape, although ellipsoidal particles or other non-spherical particles may also be used. The pigments may also be surface-treated, i.e.
hydrophilized or hydrophobized. Typical examples are coated titanium dioxides, for example Titandioxid T 805 (Degussa) or Eusolex 12000, Eusolex T, Eusolex T-ECO, Eusolex T-S, Eusolex 1-Aqua, Eusolex T-45D (all from Merck), Uvinul TiO2 (BASF). Suitable hydrophobic coating materials are, above all, silicones and, among these, especially trialkoxyoctylsilanes or simethicones. So-called micro- or nanopigments are preferably used in sun protection products.
Micronized zinc oxide such as Z-COTE or Z-COTE HP1 is preferably used.
by weight, and more particularly 5 to 10% by weight.
. .
derivatives thereof, peptides such as D,L-carnosine, D-carnosine, L-carnosine and derivatives thereof (for example anserine), carotinoids, carotenes (for example a-carotene, I3-carotene, lycopene) and derivatives thereof, chlorogenic acid and derivatives thereof, liponic acid and derivatives thereof (for example dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (for example thioredoxine, glutathione, cysteine, cystine, cystamine and glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, y-linoleyl, cholesteryl and glyceryl esters thereof) and their salts, dilaurylthiodipropionate, distearylthiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (for example butionine sulfoximines, homocysteine sulfoximine, butionine sulfones, penta-, hexa- and hepta-thionine sulfoximine) in very small compatible dosages (for example pmol to p.mol/kg), also (metal) chelators (for example a-hydroxyfatty acids, palmitic acid, phytic acid, lactoferrin), a-hydroxy acids (for example citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and derivatives thereof, unsaturated fatty acids and derivatives thereof (for example y-linolenic acid, linoleic acid, oleic acid), folic acid and derivatives thereof, ubiquinone and ubiquinol and derivatives thereof, vitamin C and derivatives thereof (for example ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (for example vitamin E acetate), vitamin A and derivatives (vitamin A palmitate), and coniferyl benzoate of benzoin resin, rutinic acid and derivatives thereof, a-glycosyl rutin, ferulic acid, furfurylidene glucitol, carnosine, butyl hydroxytoluene, butyl hydroxyanisole, nordihydroguaiac resin acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and derivatives thereof, ma nnose and derivatives thereof, superoxide dismutase, zinc and derivatives thereof (for example ZnO, ZnSO4), selenium and derivatives thereof (for example selenium methionine), stilbenes and derivatives thereof (for example stilbene oxide, trans-stilbene oxide) and derivatives of these active substances suitable for the purposes of the invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids).
Body odors arise as a result of the effect of skin bacteria on apocrine perspiration, with the formation of degradation products which have an unpleasant odor. Accordingly, deodorants comprise active ingredients which act as antimicrobial agents, enzyme inhibitors, odor absorbers or odor masking agents.
These are preferably trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and, in particular, triethyl citrate (Hydagen* CAT).
The substances inhibit enzyme activity, thereby reducing the formation of odor. Other substances which are suitable esterase inhibitors are sterol sulfates or phosphates, for example lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and esters thereof, for example glutaric acid, monoethyl glutarate, diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid and diethyl malonate, hydroxycarboxylic acids and esters thereof, for example citric acid, malic acid, tartaric acid or diethyl tartrate, and zinc glycinate.
They comprise, for example, as their main constituent, a complex zinc salt of ricinoleic acid or specific, largely odor-neutral fragrances which are known to the person skilled in the art as "fixatives", such as extracts of labdanum or styrax or certain abietic acid derivatives. The odor masking agents are fragrances or perfume oils, which, in addition to their function as odor masking agents, give the deodorants their respective fragrance note. Perfume oils which may be mentioned are, for example, mixtures of natural and synthetic fragrances. Natural fragrances are extracts from flowers, stems and leaves, fruits, fruit peels, roots, woods, herbs and grasses, needles and branches, and resins and balsams. Also suitable are animal products, such as civet and castoreum.
Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol, and hydrocarbon type. Fragrance compounds of the ester type are, for example, benzyl acetate, p-tert-butylcyclohexyl acetate, linalyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, allyl cyclohexylpropionate, styrallyl propionate and benzyl salicylate. The ethers include, for example, benzyl ethyl ether, and the aldehydes include, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial and bourgeonal, the ketones include, for example, the ionones and methyl cedryl ketone, the alcohols include anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, and the hydrocarbons include mainly the terpenes and balsams. Preference is, however, given to using mixtures of different fragrances which together produce a pleasing fragrance note. Essential oils of relatively low volatility, which are mostly used as aroma components, are also suitable as perfume oils, e.g. sage oil, camomile oil, oil of cloves, melissa oil, mint oil, cinnamon leaf oil, linden flower oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil, labdanum oil and lavandin oil. Preference is given to using bergamot oil, dihydromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol, a-hexylcinnamaldehyde, geraniol, benzylacetone, cyclamen aldehyde, linalool, boisambrene forte, ambroxan, indole, hedione, sandelice, lemon oil, mandarin oil, orange oil, allyl amyl glycolate, cyclovertal, lavandin oil, clary sage oil, 13-damascone, geranium oil bourbon, cyclohexyl salicylate, Vertofix coeur, iso-. . CA 02977566 2017-08-23 . .
E-super, Fixolide NP, evernyl, iraldein gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, romilat, irotyl and floramat alone or in mixtures.
= astringent active ingredients, = oil components, = nonionic emulsifiers, = co-emulsifiers, = bodying agents, = auxiliaries in the form of, for example, thickeners or complexing agents and/or = non-aqueous solvents such as ethanol, propylene glycol and/or glycerol:
Suitable astringent antiperspirant active ingredients are primarily salts of aluminium, zirconium or of zinc. Such suitable antihydrotic active ingredients are, for example, aluminium chloride, aluminium chlorohydrate, aluminium dichlorohydrate, aluminium sesquichlorohydrate and complex compounds thereof, e.g. with 1,2-propylene glycol, aluminium hydroxyallantoinate, aluminium chloride tartrate, aluminium zirconium trichlorohydrate, aluminium zirconium tetrachlorohydrate, aluminium zirconium pentachlorohydrate and complex compounds thereof, e.g. with amino acids, such as glycine. Oil-soluble and water-soluble auxiliaries typically encountered in antiperspirants may also be present in relatively small amounts. Such oil-soluble auxiliaries include, for example:
= inflammation-inhibiting, skin-protecting or pleasant-smelling essential oils, = synthetic skin-protecting agents and/or = oil-soluble perfume oils.
= CA 02977566 2017-08-23
(protein-undecylenic acid condensate), zinc pyrithione, aluminum pyrithione and magnesium pyrithione/dipyrithione magnesium sulfate.
= preservatives and antimicrobial substances such as p- hydroxybenzoic acid methyl, ethyl or propyl ester, sodium sorbate, sodium benzoate, bromochlorophen, phenylsalicylic acid esters, thymol and the like;
= anti-tartar active ingredients, e.g. organophosphates such as 1-hydroxyethane-1,1-diphosphonic acid, 1-phosphonopropane-1,2,3-tricarboxylic acid and others, which are known e.g. from US 3,488,419, DE 2224430 Al and DE 2343196 Al;
= other caries-inhibiting substances such as sodium fluoride, sodium monofluorophosphate, tin fluoride;
= sweeteners, such as saccharin sodium, sodium cyclamate, sucrose, lactose, maltose, fructose or Aspartame (L-aspartyl-L-phenylalanine methyl ester), Stevia extracts or sweetening constituents thereof, in particular Ribeaudioside;
= additional flavoring agents such as eucalyptus oil, anise oil, fennel oil, caraway oil, methyl acetate, cinnamaldehyde, anethol, vanillin, thymol, and mixtures of these and other natural and synthetic flavoring agents;
= pigments such as titanium dioxide;
= dyes;
= buffer substances such as primary, secondary or tertiary alkali metal phosphates or citric acid/sodium citrate;
= wound-healing and anti-inflammatory substances such as allantoin, urea, azulene, chamomile active ingredients and acetylsalicylic acid derivatives.
= . CA 02977566 2017-08-23 [002121 In mouthwashes, a combination with aqueous-alcoholic solutions of varying concentration gradients of essential oils, emulsifiers, astringent and toning drug extracts, tartar-preventing, antibacterial additives and taste correctives is directly possible. A further preferred embodiment of the invention is a mouthwash in the form of an aqueous or aqueous-alcoholic -- solution comprising the mixture of menthofuran and menthol compounds in amounts of 0.5 to 2% by weight. In mouthwashes which are diluted prior to use, adequate effects can be achieved with higher concentrations corresponding to the intended dilution ratio.
[00213] Hydrotropes [00214] In order to improve flow behavior, hydrotropes such as ethanol, isopropyl alcohol, or polyols can be used; these substances largely correspond to the carriers specified above. Polyols which are suitable here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups.
The polyols can also contain further functional groups, in particular amino groups, or be modified -- with nitrogen. Typical examples are:
= glycerol;
= alkylene glycols, such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, -- hexylene glycol, and polyethylene glycols with an average molecular weight of 100 to 1000 daltons;
= technical-grade oligoglycerol mixtures with an intrinsic degree of condensation of 1.5 to 10 such as technical-grade diglycerol mixtures with a diglycerol content of 40 to 50% by weight;
= methylol compounds, more particularly trimethylolethane, trimethylolpropane, trimethylol-butane, pentaerythritol, and dipentaerythritol;
= lower alkyl glucosides, more particularly those with 1 to 8 carbon atoms in the alkyl radical, -- such as methyl and butyl glucoside;
= sugar alcohols with 5 to 12 carbon atoms, such as sorbitol or mannitol, = sugars with 5 to 12 carbon atoms, such as glucose or saccharose;
= amino sugars such as glucamine;
, . CA 02977566 2017-08-23 = dialcohol amines, such as diethanolamine or 2-amino-1,3-propanediol.
[00215] Preservatives [00216] Examples of suitable preservatives include phenoxyethanol, formaldehyde solution, parabens, pentane diol, or sorbic acid as well as the silver complexes known under the name Surfacine. and the other substance classes listed in Annex 6, Part A and B of the Cosmetics Directive.
[00217] Dyes [00218] Substances that are suitable and approved for cosmetic purposes can be used as dyes, such as those listed in the publication "Cosmetic Coloring Agents" of the Colorant Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106.
Examples include Cochineal Red A (C.I. 16255), Patent Blue V (C.I. 42051), indigotin (C.I. 73015), chlorophyllin (C.I. 75810), Quinoline Yellow (C.I. 47005), titanium dioxide (C.I. 77891), Indanthrene Blue RS (C.I. 69800) and madder lake (C.I. 58000). Luminol can also be included as a luminescent dye. These dyes are ordinarily used in concentrations of 0.001 to 0.1% by weight, relative to the total mixture.
[00219] The total amount of the auxiliary substances and additives can be 1 to 50, and preferably 5 to 40% by weight relative to the dyes. The production of the dyes can be carried out by common cold or hot processes; the phase inversion temperature method is preferred.
[00220] USES
[00221] Further subject matter of the invention relates on the one hand to the use of hydrophobically modified hydroxyalkyl guar compounds for the stabilizing of aqueous dispersions that contain perfume oils and encapsulated fragrances and on the other to the use of production of cosmetic preparations and detergents and cleaning agents according to the invention, with the amount contained preferably being about 0.1 to about 5% by weight and more particularly about 0.5 to about 2% by weight.
EXAMPLES
PRODUCTION EXAMPLES
[00222] Model formulations are given in Table 1 below; all amounts indicated are to be understood as % by weight.
[00223] Table 1 Model formulations Fragrance SOFT SHINE 985365 70 70 70 70 Fragrance STAR TREK 987648 70 70 70 70 Fragrance 985272 BLUE JOY
Symcap K2LD 20 20 Symcap G 20 20 Symcap FS ST 20 20 Symcap K FS 20 20 Solubilizer 660352 0.1 0.1 0.2 0.2 Water to 100 Esaflor HM 22 Powder 0.05 0.08 0.05 0.1 0.06 0.1 0.06 0.1 Fragrance SOFT SHINE 985365 80 80 80 80 Fragrance STAR TREK 987648 Fragrance 985272 BLUE JOY 70 70 70 70 Symcap K2LD 20 10 Symcap G - 20 10 Symcap FS ST 20 10 Symcap K FS 20 10 Solubilizer 660352 0.1 0.1 0.05 0.08 Water to 100 Esaflor HM 22 Powder 0.05 0.06 0.06 0.05 0.05 0.07 0.05 0.05 V a = CA 02977566 2017-08-23 I a =
Production: Prepare the perfume oil, and then add remaining components in the order indicated while stirring (propeller stirrer). Stir until a homogenous mixture is obtained.
APPLICATION EXAMPLES
[00224] Dispersions 1 through 8 according to the invention and comparative dispersions V1 and V2 were stored for a period of 6 weeks at 5, 20 and 40 C respectively.
[00225] Capsule types A through D were used. The capsules were produced according to methods commonly known to the person skilled in the art; the following are the respective substances of which the capsule shells were composed:
Capsule A: melamine-formaldehyde resin (Symcap FS ST) Capsule B: melamine-formaldehyde resin (Symcap K LD) Capsule C: melamine-formaldehyde resin (Symcap K FS<) Capsule D: Polyurethane (Symcap G) [00226] The stability of the formulations was optically assessed, more particularly with respect to homogeneity of the phase. This assessment was carried out according to the following classification:
(+++) = no phase separation, (++) = minor phase separation, (+) = clear phase separation, (0) = strong phase separation.
[00227] The results are summarized in Tables 2a and 2b:
[00228] Table 2A
Stability test - Composition of the dispersions , = = CA 02977566 2017-08-23 = = I
Composition of dispersion 1 2 3 4 5 6 7 8 V1 Citrus oil 60.0 70.0 60.0 70.0 60.0 70.0 60.0 70.0 60.0 70.0 Symcap FS ST 15.0 10.0 -- - - - - -B) Symcap K LD - - - 15.0 10.0 -- - 15.0 10.0 C) Symcap K FS - - - - 15.0 10.0 -- -D) Symcap G - - - - - -15.0 10.0 - -ESAFLOR HM22 0.05 0.05 0.05 0.05 0.05 0.05 0.05 - -Water to 100 to 100 [00229] Table 2B
Stability test ¨ Storage stability Composition of dispersion 1 2 3 4 5 6 7 8 V1 1 week, 5 C +++ +++ +++ +++ +++ +++ +++ +++ 0 0 2 Weeks, 5 C +++ +++ +++ +++ +++ +++ +++ +++ 0 0 4 Weeks, 5 C +++ +++ +++ +++ +++ +++ +++ +++ 0 0 6 Weeks, 5 C +++ +++ +++ +++ +++ +++ +++ +++ 0 0 1 Week, 20 C +++ +++ +++ +++ +++ +++ +++ +++ 0 0 2 Weeks, 20 C +++ +++ +++ +++ +++ +++ +++ +++ 0 0 4 Weeks, 20 C +++ +++ +4-+ +++ +++ +++ +++ +++ 0 0 6 Weeks, 20 C ++ ++ ++ + ++ + + ++
1 Week, 40 C +++ +++ +++ +++ +++ +++ +++ +++ 0 0 2 Weeks, 40 C +++ +++ +++ +++ +++ +++ +++ +++ 0 0 4 Weeks, 40 C ++ + ++ ++ ++ ++ ++ ++
6 Weeks, 40 C + + ++ + + + + + 0 [00230] In contrast to the two comparative formulations, which lost their stability after only 1 week at 5 C, all of the formulations according to the invention were completely stable over at least 4 weeks and showed losses only with storage times of 6 weeks at 40 C.
Claims (13)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15156452.3A EP3061500B1 (en) | 2015-02-25 | 2015-02-25 | Stable dispersions |
| EP15156452.3 | 2015-02-25 | ||
| PCT/EP2016/053085 WO2016134994A1 (en) | 2015-02-25 | 2016-02-14 | Stable dispersions |
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| CA2977566A1 true CA2977566A1 (en) | 2016-09-01 |
| CA2977566C CA2977566C (en) | 2023-04-25 |
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| US (2) | US10517802B2 (en) |
| EP (3) | EP3061500B1 (en) |
| JP (1) | JP6730297B2 (en) |
| CN (2) | CN107427422B (en) |
| AU (1) | AU2016223718B2 (en) |
| BR (1) | BR112017018098A2 (en) |
| CA (1) | CA2977566C (en) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019141530A1 (en) * | 2018-01-17 | 2019-07-25 | Unilever Plc | Laundry detergent |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3061500B1 (en) | 2015-02-25 | 2019-07-10 | Symrise AG | Stable dispersions |
| US11359088B2 (en) | 2015-06-30 | 2022-06-14 | BiologiQ, Inc. | Polymeric articles comprising blends of PBAT, PLA and a carbohydrate-based polymeric material |
| US11149144B2 (en) | 2015-06-30 | 2021-10-19 | BiologiQ, Inc. | Marine biodegradable plastics comprising a blend of polyester and a carbohydrate-based polymeric material |
| US10919203B2 (en) | 2015-06-30 | 2021-02-16 | BiologiQ, Inc. | Articles formed with biodegradable materials and biodegradability characteristics thereof |
| US11111363B2 (en) | 2015-06-30 | 2021-09-07 | BiologiQ, Inc. | Articles formed with renewable and/or sustainable green plastic material and carbohydrate-based polymeric materials lending increased strength and/or biodegradability |
| US11926940B2 (en) | 2015-06-30 | 2024-03-12 | BiologiQ, Inc. | Spunbond nonwoven materials and fibers including starch-based polymeric materials |
| US10920044B2 (en) * | 2015-06-30 | 2021-02-16 | BiologiQ, Inc. | Carbohydrate-based plastic materials with reduced odor |
| US11674014B2 (en) | 2015-06-30 | 2023-06-13 | BiologiQ, Inc. | Blending of small particle starch powder with synthetic polymers for increased strength and other properties |
| US11674018B2 (en) | 2015-06-30 | 2023-06-13 | BiologiQ, Inc. | Polymer and carbohydrate-based polymeric material blends with particular particle size characteristics |
| US11879058B2 (en) | 2015-06-30 | 2024-01-23 | Biologiq, Inc | Yarn materials and fibers including starch-based polymeric materials |
| US11046840B2 (en) | 2015-06-30 | 2021-06-29 | BiologiQ, Inc. | Methods for lending biodegradability to non-biodegradable plastic materials |
| US11926929B2 (en) | 2015-06-30 | 2024-03-12 | Biologiq, Inc | Melt blown nonwoven materials and fibers including starch-based polymeric materials |
| US11111355B2 (en) | 2015-06-30 | 2021-09-07 | BiologiQ, Inc. | Addition of biodegradability lending additives to plastic materials |
| US10995201B2 (en) | 2015-06-30 | 2021-05-04 | BiologiQ, Inc. | Articles formed with biodegradable materials and strength characteristics of the same |
| EP3360951B1 (en) * | 2017-02-08 | 2020-08-12 | Henkel AG & Co. KGaA | Composition comprising perfumed oil and encapsulated perfumes |
| EP3684898B1 (en) | 2017-09-22 | 2025-04-30 | Symrise AG | Method for producing an active substance wafer |
| CN111615551B (en) * | 2018-01-17 | 2021-10-01 | 联合利华知识产权控股有限公司 | laundry detergent |
| CN108313367A (en) * | 2018-02-27 | 2018-07-24 | 湖南尔康制药股份有限公司 | A kind of vitamin C Yinqiao tablet of filling with inert gas packaging |
| WO2019170222A1 (en) | 2018-03-06 | 2019-09-12 | Symrise Ag | Encapsulated active substance deposition on hairs and textile |
| WO2019174713A1 (en) | 2018-03-12 | 2019-09-19 | Symrise Ag | Active substance adhesive film |
| WO2019179597A1 (en) | 2018-03-19 | 2019-09-26 | Symrise Ag | Water-soluble release forms for an active substance |
| CA3102614C (en) | 2018-06-15 | 2023-02-28 | Ecolab Usa Inc. | Enhanced peroxygen stability using fatty acid in bleach activating agent containing peroxygen solid |
| CN109908846B (en) * | 2019-03-11 | 2021-06-08 | 河北科技大学 | Microcapsule and preparation method and application thereof |
| EP4065180B1 (en) * | 2019-11-29 | 2024-11-27 | Symrise AG | Rim block with improved scent performance |
| US11427794B2 (en) | 2019-12-19 | 2022-08-30 | Henkel Ag & Co. Kgaa | Low density unit dose detergents based on butyl cellosolve with encapsulated fragrance |
| CN111593588A (en) * | 2020-06-01 | 2020-08-28 | 苏州大邦纺织有限公司 | Modified laccase soaping agent for soaping cotton fabrics and preparation method thereof |
| CN111700821A (en) * | 2020-07-14 | 2020-09-25 | 广州卓芬化妆品有限公司 | Milky perfume and preparation method thereof |
| FR3113493B1 (en) * | 2020-08-20 | 2023-08-11 | Benu Blanc | PERFUMED COMPOSITION FOR MANUFACTURING AN OLFACTORY SUPPORT |
| US12593840B2 (en) | 2022-01-24 | 2026-04-07 | Optimally Balanced Corp. | Pesticidal or repellant composition and method of use |
| WO2023186333A1 (en) | 2022-03-30 | 2023-10-05 | Symrise Ag | Paper roll as fragrance control release system |
| EP4279570A1 (en) | 2022-05-19 | 2023-11-22 | The Procter & Gamble Company | A process for making a particulate laundry detergent composition |
| CN115739188B (en) * | 2022-11-07 | 2024-02-13 | 山东新和成药业有限公司 | A kind of cyclization heterogeneous catalyst, its preparation method and its application in the preparation of L-isopulegol from R-citronellal |
Family Cites Families (86)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US387052A (en) | 1888-07-31 | Spring-vehicle | ||
| US3415758A (en) | 1960-03-09 | 1968-12-10 | Ncr Co | Process of forming minute capsules en masse |
| NL149701C (en) | 1965-12-08 | 1981-05-15 | Procter & Gamble | METHOD FOR PREPARING AN AGENT TOOTHIC CARE, WHICH INCLUDES A PHOSPHONIC ACID DERIVATIVE AS AN ACTIVE INGREDIENT, AND FORMED TOOTHIC CARE. |
| US3516941A (en) | 1966-07-25 | 1970-06-23 | Minnesota Mining & Mfg | Microcapsules and process of making |
| DE2224430C3 (en) | 1972-05-19 | 1980-10-09 | Henkel Kgaa, 4000 Duesseldorf | Oral and dental care products that prevent tartar formation |
| DE2343196C3 (en) | 1973-08-27 | 1980-01-10 | Henkel Kgaa, 4000 Duesseldorf | Aiacycloalkan-2 ^ -diphosphonic acids or their water-soluble salts |
| NL180807C (en) | 1975-12-26 | 1987-05-04 | Morishita Jintan Co | DEVICE FOR MANUFACTURING SEAMLESS MATERIAL FILLED CAPSULES. |
| DE2940786A1 (en) | 1979-10-08 | 1981-04-16 | Basf Ag, 6700 Ludwigshafen | METHOD FOR PRODUCING MICROCAPSULES |
| DE2950694A1 (en) | 1979-12-17 | 1981-06-25 | Bayer Ag, 5090 Leverkusen | METHOD FOR THE PRODUCTION OF NEUTRAL PHOSPHORIGOIC ACID ALTERES |
| US4428869A (en) * | 1981-08-20 | 1984-01-31 | International Flavors & Fragrances Inc. | Cologne consisting of microcapsule suspension |
| CA1238917A (en) | 1984-01-31 | 1988-07-05 | Vivian B. Valenty | Detergent builder |
| US4524009A (en) | 1984-01-31 | 1985-06-18 | A. E. Staley Manufacturing Company | Detergent builder |
| US4639325A (en) | 1984-10-24 | 1987-01-27 | A. E. Staley Manufacturing Company | Detergent builder |
| JPH01193216A (en) | 1988-01-29 | 1989-08-03 | Fuji Kapuseru Kk | Soft capsule and globular article |
| CA2015737C (en) * | 1989-05-11 | 1995-08-15 | Diane Grob Schmidt | Coated perfume particles |
| DE69020861T2 (en) | 1989-11-10 | 1995-11-30 | Tno | Process for the preparation of polydicarboxysaccharides. |
| IT1249883B (en) | 1990-08-13 | 1995-03-30 | Ferruzzi Ricerca & Tec | CALCIUM SEQUESTRING AGENTS BASED ON OXIDIZED CARBOHYDRATES AND THEIR USE AS BUILDER FOR DETERGENTS |
| IT1245063B (en) | 1991-04-12 | 1994-09-13 | Ferruzzi Ricerca & Tec | PROCEDURE FOR OXIDATION OF CARBOHYDRATES |
| US5135747A (en) * | 1991-05-17 | 1992-08-04 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Deodorant/antiperspirant products with fragrance and encapsulated odor counteractant |
| DE4134914A1 (en) | 1991-10-23 | 1993-04-29 | Henkel Kgaa | DETERGENT AND CLEANING AGENT WITH SELECTED BUILDER SYSTEMS |
| ATE166362T1 (en) | 1991-11-14 | 1998-06-15 | Procter & Gamble | C6/C2-C3 OXIDIZED STARCH AS A DETERGENT INGREDIENT |
| JPH05339896A (en) | 1992-06-03 | 1993-12-21 | Arakawa Chem Ind Co Ltd | Paper sizing agent and paper sizing |
| DE4317519A1 (en) | 1993-05-26 | 1994-12-01 | Henkel Kgaa | Production of polysaccharide-based polycarboxylates |
| DE4321022A1 (en) | 1993-06-24 | 1995-01-05 | Henkel Kgaa | Sulphated mixed hydroxy ethers |
| NL194919C (en) | 1993-09-07 | 2003-07-04 | Tno | Process for oxidizing carbohydrates. |
| NL9301905A (en) | 1993-11-04 | 1995-06-01 | Inst Voor Agrotech Onderzoek | Method for oxidizing carbohydrates. |
| WO1995016432A2 (en) * | 1993-12-07 | 1995-06-22 | The Procter & Gamble Company | Cosmetic cleansing composition with dual blooming perfume system |
| DE4402051A1 (en) | 1994-01-25 | 1995-07-27 | Henkel Kgaa | Builder for detergents or cleaners |
| DE4402851A1 (en) | 1994-01-31 | 1995-08-03 | Henkel Kgaa | Fluid bed oxidation process for the production of polysaccharide-based polycarboxylates |
| DE19503061A1 (en) | 1995-02-01 | 1996-08-08 | Henkel Kgaa | Dimer alcohol bis- and trimer alcohol tris-sulfates and ether sulfates |
| DE19513391A1 (en) | 1995-04-08 | 1996-10-10 | Henkel Kgaa | End gp.-capped dimer alcohol- and trimer alcohol alkoxylate(s) |
| FR2746010B1 (en) | 1996-03-12 | 1998-04-24 | STABLE GEL-IN-OIL EMULSION AND ITS USE IN THE COSMETIC, DERMATOLOGICAL, VETERINARY AND / OR AGRI-FOOD FIELDS | |
| FR2773472B1 (en) * | 1998-01-13 | 2002-10-11 | Oreal | TICTORIAL COMPOSITION AND METHODS FOR DYEING KERATINIC FIBERS USING THE SAME |
| DE19810011A1 (en) | 1998-03-09 | 1999-09-16 | Henkel Kgaa | Use of alkylgalactomannans as interface stabilizers to remove need for homogenization of water/oil emulsions |
| WO1999047253A1 (en) | 1998-03-19 | 1999-09-23 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Fabrication of multilayer-coated particles and hollow shells via electrostatic self-assembly of nanocomposite multilayers on decomposable colloidal templates |
| US6214376B1 (en) | 1998-08-25 | 2001-04-10 | Banner Pharmacaps, Inc. | Non-gelatin substitutes for oral delivery capsules, their composition and process of manufacture |
| DE19842788A1 (en) | 1998-09-18 | 2000-03-23 | Beiersdorf Ag | Emulsifier-free finely dispersed systems of the oil-in-water and water-in-oil type |
| DE59912559D1 (en) | 1999-07-02 | 2005-10-20 | Cognis Ip Man Gmbh | Microcapsules - III |
| ES2213948T3 (en) | 1999-07-02 | 2004-09-01 | Cognis Iberia, S.L. | MICROCAPSULES II. |
| EP1064910B1 (en) | 1999-07-02 | 2005-09-14 | Cognis IP Management GmbH | Microcapsules |
| EP1064912B1 (en) | 1999-07-02 | 2004-01-28 | Cognis Iberia, S.L. | Microcapsules |
| DE10000223A1 (en) | 2000-01-05 | 2001-07-12 | Basf Ag | Microcapsules which are useful in, e.g. detergent or skin care compositions, can release a fragrance from a hydrophobic core when the polymer coating of the capsule is broken down |
| US7758888B2 (en) * | 2000-04-21 | 2010-07-20 | Sol-Gel Technologies Ltd. | Composition exhibiting enhanced formulation stability and delivery of topical active ingredients |
| HUP0402425A3 (en) | 2001-11-23 | 2005-11-28 | Unilever Nv | Water continuous food product with cooling flavour |
| DE10163142A1 (en) | 2001-12-20 | 2003-07-10 | Henkel Kgaa | Polymeric fragrance capsules and their manufacture |
| DE10164110A1 (en) | 2001-12-24 | 2003-07-10 | Dragoco Gerberding Co Ag | Mononuclear filled microcapsules |
| US20030161802A1 (en) | 2002-02-05 | 2003-08-28 | Flammer Linda J. | Anti-dandruff and anti-itch compositions containing sensate and sensate enhancer-containing compounds |
| EP1709958A1 (en) | 2002-12-05 | 2006-10-11 | Symrise GmbH & Co. KG | Seamless filled capsules |
| EP1694810B2 (en) * | 2003-12-19 | 2014-08-27 | Unilever N.V. | Detergent granules and process for their manufacture |
| US20050226900A1 (en) * | 2004-04-13 | 2005-10-13 | Winton Brooks Clint D | Skin and hair treatment composition and process for using same resulting in controllably-releasable fragrance and/or malodour counteractant evolution |
| EP1637188A1 (en) | 2004-08-20 | 2006-03-22 | Firmenich Sa | Improved liquid/sprayable compositions comprising fragranced aminoplast capsules |
| DE602006011288D1 (en) * | 2005-03-16 | 2010-02-04 | Symrise Gmbh & Co Kg | MENTHOLDING SOLIDS COMPOSITION |
| EP1984486B1 (en) * | 2006-04-04 | 2010-01-13 | Unilever PLC | Laundry composition with encapsulated liquid benefit agent |
| US20080050320A1 (en) * | 2006-08-23 | 2008-02-28 | Ariel Haskel | Skin care compositions containing a hydrophobic material and related methods |
| JP2008063419A (en) * | 2006-09-06 | 2008-03-21 | Lion Corp | Medium bulk density detergent for clothing and method for producing the same |
| MX2009005248A (en) * | 2006-11-22 | 2009-05-28 | Appleton Paper Inc | Benefit agent containing delivery particle. |
| CN101541939A (en) * | 2006-11-22 | 2009-09-23 | 阿普尔顿纸张公司 | Benefit agent-containing delivery particle |
| US7959955B1 (en) * | 2007-06-15 | 2011-06-14 | The Akshay Wellness Group, Inc. | Antipyrotic formulation for the treatment of epidermal burns |
| JP5547093B2 (en) * | 2008-02-15 | 2014-07-09 | ザ プロクター アンド ギャンブル カンパニー | Delivery particle |
| US20090253612A1 (en) | 2008-04-02 | 2009-10-08 | Symrise Gmbh & Co Kg | Particles having a high load of fragrance or flavor oil |
| DE102008051799A1 (en) | 2008-10-17 | 2010-04-22 | Henkel Ag & Co. Kgaa | Stabilization of microcapsule slurries |
| DE102008059448A1 (en) * | 2008-11-27 | 2010-06-02 | Henkel Ag & Co. Kgaa | Perfumed washing or cleaning agent |
| JP2010180284A (en) * | 2009-02-03 | 2010-08-19 | Lion Corp | Granular detergent composition and method for manufacturing the same |
| US9993793B2 (en) * | 2010-04-28 | 2018-06-12 | The Procter & Gamble Company | Delivery particles |
| US20110269657A1 (en) * | 2010-04-28 | 2011-11-03 | Jiten Odhavji Dihora | Delivery particles |
| CA2844631A1 (en) * | 2011-08-09 | 2013-02-14 | Rhodia Operations | Wettable, non-leachable peat moss, method of preparation, and method of use |
| CN103747772B (en) * | 2011-08-24 | 2016-03-16 | 荷兰联合利华有限公司 | Comprise the benefit agent delivery particle of nonionic polysaccharide |
| PH12014500305A1 (en) * | 2011-08-24 | 2014-03-31 | Unilever Nv | Benefit agent delivery particles comprising non-ionic polysaccharides |
| US20150044262A1 (en) | 2011-12-22 | 2015-02-12 | Givaudan S.A. | Encapsulation of perfumes |
| EP2689835B1 (en) | 2012-07-26 | 2019-05-08 | Papierfabrik August Koehler SE | Aromatic oil encapsulation |
| EP2711414B1 (en) | 2012-09-19 | 2019-05-15 | Symrise AG | Stabilisation of capsule systems in detergent and cleaning compositions |
| TWI646978B (en) * | 2012-10-25 | 2019-01-11 | Givaudan Sa | capsule |
| MX367307B (en) * | 2012-12-14 | 2019-08-14 | Procter & Gamble | ANTIPERSPIRANT and DEODORANT COMPOSITIONS. |
| DE102012223423A1 (en) | 2012-12-17 | 2014-06-18 | Henkel Ag & Co. Kgaa | Washing, cleaning or care products containing fragrance particles |
| US9340757B2 (en) * | 2013-04-18 | 2016-05-17 | The Procter & Gamble Company | Fragrance materials |
| JP6256905B2 (en) | 2013-06-07 | 2018-01-10 | 株式会社 資生堂 | Fragrance-encapsulating capsule and cosmetics containing the same |
| WO2015014628A1 (en) * | 2013-07-31 | 2015-02-05 | Unilever Plc | Composition comprising a triggered release system |
| CN105492588A (en) * | 2013-08-28 | 2016-04-13 | 宝洁公司 | Detergents or cleaners containing microcapsules |
| WO2015041791A1 (en) * | 2013-09-23 | 2015-03-26 | The Procter & Gamble Company | Particles |
| ES2671409T3 (en) * | 2014-01-27 | 2018-06-06 | Firmenich Sa | Procedure to prepare aminoplastic microcapsules |
| WO2015155286A1 (en) * | 2014-04-10 | 2015-10-15 | Unilever Plc | Process to manufacture an externally structured isotropic aqueous detergent liquid |
| WO2016003948A1 (en) * | 2014-06-30 | 2016-01-07 | The Procter & Gamble Company | Personal care compositions and methods |
| US20170216166A1 (en) * | 2014-10-01 | 2017-08-03 | International Flavors & Fragrances Inc. | Capsules containing polyvinyl alcohol |
| US20170304163A1 (en) * | 2014-11-07 | 2017-10-26 | Givaudan Sa | Improvements in or relating to organic compounds |
| ES2667487T3 (en) * | 2014-12-08 | 2018-05-11 | Takasago International Corporation | Cosmetic compositions with rinsing |
| EP3061500B1 (en) | 2015-02-25 | 2019-07-10 | Symrise AG | Stable dispersions |
-
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019141530A1 (en) * | 2018-01-17 | 2019-07-25 | Unilever Plc | Laundry detergent |
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| AU2016223718A1 (en) | 2017-09-14 |
| US10342748B2 (en) | 2019-07-09 |
| US20180049957A1 (en) | 2018-02-22 |
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| CN107427422B (en) | 2021-12-21 |
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| WO2016134977A1 (en) | 2016-09-01 |
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| US10517802B2 (en) | 2019-12-31 |
| EP3061500B1 (en) | 2019-07-10 |
| CN107427422A (en) | 2017-12-01 |
| US20180051238A1 (en) | 2018-02-22 |
| JP6730297B2 (en) | 2020-07-29 |
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