CN117897223A - Plant protein-based microcapsules - Google Patents
Plant protein-based microcapsules Download PDFInfo
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- CN117897223A CN117897223A CN202280058156.8A CN202280058156A CN117897223A CN 117897223 A CN117897223 A CN 117897223A CN 202280058156 A CN202280058156 A CN 202280058156A CN 117897223 A CN117897223 A CN 117897223A
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- Prior art keywords
- protein
- microcapsules
- shell
- group
- oil
- Prior art date
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Landscapes
- Fats And Perfumes (AREA)
Abstract
The present invention relates to a novel process for preparing plant protein-based microcapsules. Vegetable protein-based microcapsules are also an object of the present invention. Perfuming compositions and consumer products, in particular perfumed consumer products in the form of household care or personal care products, comprising said microcapsules are also part of the invention.
Description
Technical Field
The present invention relates to a novel process for preparing plant protein-based microcapsules. Vegetable protein-based microcapsules are also an object of the present invention. Perfuming compositions and consumer products, in particular perfumed consumer products in the form of household care or personal care products, comprising said microcapsules are also part of the invention.
Background
One of the problems faced by the perfumery industry is that the olfactive benefit provided by odoriferous compounds is lost relatively quickly due to their volatility, particularly the volatility of "top notes". In order to adjust the release rate of the volatiles, a delivery system (e.g., microcapsules containing perfume) is required to protect and release the core payload upon triggering. A key requirement in the industry for these systems is to be able to maintain suspension in the challenging base without physical decomposition or degradation. This is referred to as stability of the delivery system. For example, fragrance personal and household cleaners containing high levels of aggressive surfactant detergents are very challenging for microcapsule stability.
Polyurea and polyurethane based microcapsule slurries are widely used in, for example, the fragrance industry because they provide a durable and pleasant olfactory effect after application to different substrates. Such microcapsules have been widely disclosed in the prior art (see e.g. WO 2007/004166 or EP 2300146).
In addition to performance in terms of stability and olfactory performance, consumer demand for eco-friendly delivery systems is becoming more and more important and development of new delivery systems is being driven.
Thus, there remains a need to provide new microcapsules using more eco-friendly materials, while not compromising the performance of the microcapsules, in particular in terms of stability in challenging media such as consumer product bases, and in terms of providing olfactory performance in the case of active ingredient delivery, e.g. in the case of perfuming ingredients.
The present invention proposes a solution to the above-mentioned problems by providing novel plant protein-based microcapsules and a method for preparing the microcapsules.
Disclosure of Invention
It has now been found that core-shell microcapsules encapsulating a hydrophobic material can be obtained by reacting a multifunctional monomer (e.g. an acid chloride) with an optionally used reactant (e.g. at least one amino compound) in the presence of a plant-based protein. The microcapsules of the present invention thus provide a solution to the above-mentioned problems, as they allow the preparation of eco-friendly microcapsules having the required stability in challenging binders.
In a first aspect, the present invention relates to a core-shell microcapsule comprising:
a core comprising a hydrophobic material, preferably a perfume oil, and
-a polymeric shell comprising a protein selected from the group consisting of potato protein, chickpea protein, pea protein, algae protein, broad bean protein, barley protein, oat protein, wheat gluten protein, lupin protein and mixtures thereof.
Another object of the present invention is a core-shell microcapsule slurry comprising at least one microcapsule comprising:
a core comprising a hydrophobic material, preferably a perfume oil, and
-a polymeric shell comprising a protein selected from the group consisting of potato protein, chickpea protein, pea protein, algae protein, broad bean protein, barley protein, oat protein, wheat gluten protein, lupin protein and mixtures thereof.
Another object of the present invention is a method for preparing a core-shell microcapsule slurry comprising the steps of:
a) Preparing an oil phase comprising a hydrophobic material, preferably a perfume, to form an oil phase;
b) Dispersing the oil phase obtained in step a) into an aqueous phase to form an oil-in-water emulsion;
c) Performing a curing step to form microcapsules in the form of a slurry;
wherein the polyfunctional monomer is added to the oil phase and/or the water phase, and
wherein a protein selected from the group consisting of potato protein, chickpea protein, pea protein, algae protein, fava bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof is added to the oil phase and/or the water phase.
The invention also relates to a perfumed consumer product and a flavoured edible product comprising microcapsules as defined above.
Detailed Description
Unless otherwise indicated, percentages (%) refer to weight percentages of the composition.
By "active ingredient" is meant a single compound or a combination of ingredients.
By "perfume oil or flavor (flavor) oil" is meant a single perfuming or flavoring compound, or a mixture of several perfuming or flavoring compounds.
By "consumer product" or "end product" is meant a manufactured product that is ready for distribution, sale, and use by a consumer.
For the sake of clarity, the expression "dispersion" in the present invention refers to a system in which the particles are dispersed in continuous phases of different composition, and it specifically includes suspensions or emulsions.
In the present invention, by "microcapsule" or similar expression, it is meant that the core-shell microcapsules have a particle size distribution in the micrometer range (e.g., an average diameter (d (v, 0.5)) of about 1 to 3000 micrometers, preferably 1 to 500 micrometers), and comprise an outer solid polymer-based shell and an inner continuous oil phase surrounded by an outer shell. According to a particular embodiment, the polymeric shell is a polyamide-based shell.
By "microcapsule slurry" is meant microcapsules dispersed in a liquid. According to one embodiment, the slurry is an aqueous slurry, i.e. the microcapsules are dispersed in an aqueous phase.
By "amino compound" is understood a compound having at least two reactive amine groups.
By "polyamide-based microcapsule", "polyamide-based core-shell microcapsule" or "polyamide-based shell" is meant that the shell of the microcapsule comprises a polyamide material. The expression "polyamide-based microcapsules" may also cover shells made of a complex comprising a polyamide material and another material, such as a protein as defined in the present invention.
In the present invention, "polyamide-based microcapsules" and "polyamide microcapsules" are used indifferently. In the present invention, "polyamide-based shell" and "polyamide shell" are used indifferently.
By "multifunctional monomer" is meant a molecule that chemically reacts or combines as units to form a polymer or supramolecular polymer. The multifunctional monomer of the present invention has at least two functional groups capable of reacting or bonding with the functional groups of the other component and/or capable of polymerizing to form a polymer shell.
It has been found that core-shell microcapsules, preferably polyamide-based microcapsules, having overall good properties in challenging binders can be obtained.
Core-shell microcapsules
A first object of the present invention is a core-shell microcapsule comprising:
a core comprising a hydrophobic material, preferably a perfume oil, and
-a polymeric shell comprising a protein selected from the group consisting of potato protein, chickpea protein, pea protein, algae protein, broad bean protein, barley protein, oat protein, wheat gluten protein, lupin protein and mixtures thereof.
According to one embodiment, the protein in the polymer shell is cross-linked.
According to one embodiment, the proteins in the polymer shell are partially cross-linked.
According to one embodiment, the proteins in the polymer shell are not crosslinked.
According to one embodiment, the polymeric shell comprises polymerized multifunctional monomers.
Hydrophobic material
According to one embodiment, the core is an oil-based core.
The hydrophobic material according to the invention may be an "inert" material, such as a solvent or an active ingredient.
By "hydrophobic material" is meant any hydrophobic material that forms a two-phase dispersion when mixed with water. The hydrophobic material is typically a liquid at about 20 ℃.
According to one embodiment, the hydrophobic material is a hydrophobic active ingredient.
When the hydrophobic materials are active ingredients, they are preferably selected from the group consisting of flavors (flavours), flavor ingredients, fragrances (daily chemical fragrances), fragrance ingredients, nutraceuticals, cosmetics, pest control agents (pest), biocide active ingredients, and mixtures thereof.
According to a particular embodiment, the hydrophobic material comprises a Phase Change Material (PCM).
According to a particular embodiment, the hydrophobic material comprises a mixture of a perfume with another ingredient selected from the group consisting of nutraceuticals, cosmetics, pest control agents and biocide active ingredients.
According to a specific embodiment, the hydrophobic material comprises a mixture of a biocide active ingredient with another ingredient selected from the group consisting of fragrances, nutraceuticals, cosmetics, pest control agents.
According to a specific embodiment, the hydrophobic material comprises a mixture of a pest control agent with another ingredient selected from the group consisting of fragrances, nutraceuticals, cosmetics, biocide active ingredients.
According to a particular embodiment, the hydrophobic material comprises a perfume.
According to a particular embodiment, the hydrophobic material consists of a perfume.
According to a particular embodiment, the hydrophobic material consists of biocide active ingredients.
According to a particular embodiment, the hydrophobic material consists of a pest control agent.
By "perfume" (or also referred to as "perfume oil"), we mean herein an ingredient or composition that is liquid at about 20 ℃. According to any of the above embodiments, the perfume oil may be a single perfuming ingredient or a mixture of ingredients in the form of a perfuming composition. By "perfuming ingredient" is meant herein a compound, the main purpose of which is to impart or modulate odor. In other words, such ingredients to be considered as perfuming ingredients must be recognized by a person skilled in the art as being capable of imparting or modifying, at least in an active or pleasant way, the odor of the composition, and not just as having an odor. For the purposes of the present invention, perfume oils also include combinations of perfuming ingredients with substances which improve, enhance or modify the delivery of the perfuming ingredients, such as pro-fragrances, emulsions or dispersions, as well as combinations which confer other benefits besides altering or conferring odor, such as persistence, burst, malodour counteracting, antibacterial effect, microbial stability, pest control.
The nature and type of perfuming ingredients present in the oil phase do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the intended use or application and the desired organoleptic effect. In general, these perfuming ingredients belong to different chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenes, nitrogen-or sulfur-containing heterocyclic compounds and essential oils, and the perfuming co-ingredients can be of natural or synthetic origin. In any event, many of these co-ingredients are listed in references such as the s.arctander works Perfume and Flavor Chemicals,1969,Montclair,New Jersey,USA or newer versions thereof or other works of similar nature, as well as the patent literature that is abundant in the fragrance arts.
In particular, perfuming ingredients commonly used in perfumery formulations (formulations) can be cited, for example:
-an aldehyde fragrance component: decanal, dodecanal, 2-methylundecnal, 10-undecnal, octanal, nonanal and/or nonenal;
-aromatic herbal ingredients: eucalyptus oil, camphor, eucalyptol, 5-methyltricyclo [ 6.2.1.0-2, 7- ] undec-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4, 4-dimethyl-1, 3-oxathiane (oxathiane), 2,7/8, 9/10-tetramethylspiro [5.5] undec-8-en-1-one, menthol and/or alpha-pinene;
-balsam component: coumarin, ethyl vanillin and/or vanillin;
-citrus aroma component: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellonitrile, orange terpene, limonene, 1-p-menthen-8-yl acetate and/or 1,4 (8) -p-menthadiene;
-floral components: methyl dihydrojasmonate, linalool, citronellol, phenethyl alcohol, 3- (4-tert-butylphenyl) -2-methylpropionaldehyde, hexylcinnamaldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4 (2H) -pyranol, beta-ionone (beta-citronellone), methyl 2- (methylamino) benzoate, (E) -3-methyl-4- (2, 6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one (1E) -1- (2, 6-trimethyl-2-cyclohexen-1-yl) -1-penten-3-one, 1- (2, 6-trimethyl-1, 3-cyclohexadien-1-yl) -2-buten-1-one, (2E) -1- (2, 6-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one, (2E) -1- [2, 6-trimethyl-3-cyclohexen-1-yl ] -2-buten-1-one, (2E) -1- (2, 6-trimethyl-1-cyclohexen-1-yl) -2-buten-1-one, 2, 5-dimethyl-2-indanmethanol, 2, 6-trimethyl-3-cyclohexene-1-carboxylate, 3- (4, 4-dimethyl-1-cyclohexen-1-yl-propanal, hexyl salicylate, 3, 7-dimethyl-1, 6-nonadien-3-ol, 3- (4-isopropylphenyl) -2-methylpropanaldehyde, tricyclodecenyl acetate, geraniol, p-mentha-1-en-8-ol, 4- (1, 1-dimethylethyl) -1-cyclohexyl acetate, 1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, methyl high cis-dihydrojasmonate 3-methyl-5-phenyl-1-pentanol, tricyclodecenyl propionate, geranyl acetate, tetrahydrolinalool, cis-7-p-menthol, (S) -2- (1, 1-dimethylpropoxy) propyl propionate, 2-methoxynaphthalene, 2-trichloro-1-phenylethyl acetate, 4/3- (4-hydroxy-4-methylpentyl) -3-cyclohexene-1-carbaldehyde, pentylmennaldehyde, 8-decen-5-olide, 4-phenyl-2-butanone, isononyl acetate, 4- (1, 1-dimethylethyl) -1-cyclohexyl acetate, tricyclodecenyl isobutyrate, and/or a mixture of methyl ionone isomers;
-fruity components: gamma-undecalactone, 2, 5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1, 3-oxathiane, 4-decalactone, ethyl 2-methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonolactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1, 3-dioxolane-2-acetate, diethyl 3- (3, 3/1, 1-dimethyl-5-indanyl) propanal, diethyl 1, 4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, [ 3-ethyl-2-oxiranyl ] acetic acid 1- [3, 3-dimethylcyclohexyl ] ethyl ester and/or diethyl 1, 4-cyclohexanedicarboxylate;
green aroma component: 2-methyl-3-hexanone (E) -oxime, 2, 4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styryl acetate, allyl (2-methylbutoxy) acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z) -3-hexen-1-ol and/or 1- (5, 5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one;
-musk component: 1, 4-dioxa-5, 17-cyclopentadecyldione, (Z) -4-cyclopentadec-1-one, 3-methylcyclopentadecone, 1-oxa-12-cyclohexadec-2-one, 1-oxa-13-cyclohexadec-2-one, (9Z) -9-cyclohexadec-1-one, 2- { 1S) -1- [ (1R) -3, 3-dimethylcyclohexyl ] ethoxy } -2-hydroxyethyl propionate, 3-methyl-5-cyclopentadec-1-one, 1,3,4,6,7,8-hexahydro-4, 6,7, 8-hexamethylcyclopenta [ G ] -2-benzopyran, propionic acid (1S, 1 'R) -2- [1- (3', 3 '-dimethyl-1' -cyclohexyl) ethoxy ] -2-methylpropyl propionate, oxacyclohexadec-2-one and/or propionic acid (1S, 1 'R) - [1- (3', 3 '-dimethyl-1' -cyclohexyl) ethoxycarbonyl ] methyl propionate;
-an costustoot component: 1- [ (1 RS,6 SR) -2, 6-trimethylcyclohexyl]-3-hexanol, 3-dimethyl-5- [ (1R) -2, 3-trimethyl-3-cyclopenten-1-yl]-4-pentaAlkene-2-ol, 3,4 '-dimethyl spiro [ ethylene oxide-2, 9' -tricyclo [6.2.1.0 ] 2,7 ]Undecane [ 4]]Alkene, (1-ethoxyethoxy) cyclododecane, acetic acid 2,2,9,11-tetramethylspiro [5.5 ]]Undec-8-en-1-yl ester, 1- (octahydro-2, 3, 8-tetramethyl-2-naphthyl) -1-ethanone, patchouli oil, terpene fraction of patchouli oil,(1 'r, e) -2-ethyl-4- (2', 2',3' -trimethyl-3 '-cyclopenten-1' -yl) -2-buten-1-ol, 2-ethyl-4- (2, 3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol, methyl cedrone, 5- (2, 3-trimethyl-3-cyclopentenyl) -3-methylpent-2-ol, 1- (2, 3, 8-tetramethyl-1, 2,3,4,6,7,8 a-octahydronaphthalen-2-yl) ethan-1-one and/or isobornyl acetate;
other ingredients (e.g. amber, powder, spicy or watery): dodecahydro-3 a,6, 9 a-tetramethylnaphtho [2,1-b ] furan and any stereoisomers thereof, piperonal, anisaldehyde, eugenol, cinnamaldehyde, clove oil, 3- (1, 3-benzodioxol-5-yl) -2-methylpropanaldehyde, 7-methyl-2H-1, 5-benzodioxepin-3 (4H) -one, 2, 5-trimethyl-1, 2,3, 4a,5,6, 7-octahydro-2-naphthol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro [4.4] nonane and/or 3- (3-isopropyl-1-phenyl) butanal.
It will also be appreciated that the ingredients may also be compounds known to release various types of perfuming compounds in a controlled manner, also known as pro-fragrances (pro-fragrance) or pro-fragrance (pro-fragrance). Non-limiting examples of suitable pro-fragrances may include 4- (dodecylthio) -4- (2, 6-trimethyl-2-cyclohexen-1-yl) -2-butanone, 4- (dodecylthio) -4- (2, 6-trimethyl-1-cyclohexen-1-yl) -2-butanone, 3- (dodecylthio) -1- (2, 6-trimethyl-3-cyclohexen-1-yl) -1-butanone, 2- (dodecylthio) octan-4-one, 2-phenylethyl oxo (phenyl) acetate oxo (phenyl) acetic acid 3, 7-dimethyloct-2, 6-dien-1-yl ester, oxo (phenyl) acetic acid (Z) -hex-3-en-1-yl ester, hexadecanoic acid 3, 7-dimethyl-2, 6-octadien-1-yl ester, succinic acid bis (3, 7-dimethyloct-2, 6-dien-1-yl) ester, (2- ((2-methylundec-1-en-1-yl) oxy) ethyl) benzene, 1-methoxy-4- (3-methyl-4-phenethoxybut-3-en-1-yl) benzene, (3-methyl-4-phenethyloxy-but-3-en-1-yl) benzene, 1- (((Z) -hex-3-en-1-yl) oxy) -2-methylundec-1-ene, (2- ((2-methylundec-1-en-1-yl) oxy) ethoxy) benzene, 2-methyl-1- (oct-3-yloxy) undec-1-ene, 1-methoxy-4- (1-phenethylen-1-en-2-yl) benzene, 1-methyl-4- (1-phenethylen-1-en-2-yl) benzene, 2- (1-phenethylen-1-en-2-yl) naphthalene, (2-phenethylen-2- (1- ((3, 7-dimethyloct-6-en-1-yl) oxy) prop-1-en-2-yl) oxy) naphthalene, (2- ((2-pentylidene) methoxy) ethyl) benzene, 4-allyl-2-methoxy-1-methoxy-2-methoxy) phenyl) oxy benzene, (2- ((2-heptylcyclopentylidene) methoxy) ethyl) benzene, 1-isopropyl-4-methyl-2- ((2-pentylcyclopentylidene) methoxy) benzene, 2-methoxy-1- ((2-pentylcyclopentylidene) methoxy) -4-propylbenzene, 3-methoxy-4- ((2-methoxy-2-phenylvinyl) oxy) benzaldehyde, 4- ((2- (hexyloxy) -2-phenylvinyl) oxy) -3-methoxybenzaldehyde, or a mixture thereof.
The perfuming ingredients can be dissolved in solvents currently used in the perfumery industry. The solvent is preferably not an alcohol. Examples of such solvents are diethyl phthalate, isopropyl myristate,(rosin resins, available from Eastman), benzyl benzoate, ethyl citrate, triethyl citrate, limonene or other terpenes or isoparaffins. Preferably, the solvent is very hydrophobic and highly sterically hindered, e.g. +.>Or benzyl benzoate. Preferably, the perfume comprises less than 30% solvent. More preferably, the perfume comprises less than 20%, even more preferably less than 10% of solvent, all these percentages being by weight relative to the total weight of the perfume. Most preferably, the perfume is substantially free of solvent.
Preferred perfuming ingredients are those having a high steric hindrance, in particular those from one of the following groups:
-group 1: comprising a chain or branched chain C 1 -C 4 A perfuming ingredient of an alkyl or alkenyl substituted cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring;
-group 2: comprising a chain or branched chain C 4 -C 8 Perfuming ingredients of cyclopentane, cyclopentene, cyclopentanone or cyclopentenone rings substituted with alkyl or alkenyl substituents;
-group 3: perfuming ingredients comprising benzene rings, or comprising a perfume comprising at least one linear or branched chain C 5 -C 8 Substituted with alkyl or alkenyl substituents, or with at least one phenyl substituent and optionally with one or more linear or branched C 1 -C 3 A perfuming ingredient of an alkyl or alkenyl substituted cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring;
-group 4: comprising at least two condensed or linked C 5 And/or C 6 A perfuming ingredient of the ring;
-group 5: a perfuming ingredient comprising a camphor-like ring structure;
-group 6: comprising at least one C 7 -C 20 A perfuming ingredient of ring structure;
-group 7: a perfuming ingredient having a log p value higher than 3.5 and comprising at least one t-butyl or at least one trichloromethyl substituent;
examples of components from each of these groups are:
-group 1:2, 4-dimethyl-3-cyclohexene-1-carbaldehyde (source: firmendich SA, switzerland), isocyclocitral, menthone, isomenthone, methyl 2, 2-dimethyl-6-methylene-1-cyclohexanecarboxylate (source: firmendich SA, switzerland), nerone, terpineol, dihydroterpineol, terpene acetate, dihydroterpene acetate, dipentene, eucalyptol, caproate (hexylate), rose ether, (S) -1, 8-p-menthadien-7-ol (source: firmendich SA, switzerland), l-p-menthen-4-ol, acetic acid (1 RS,3RS,4 SR) -3-p-menthyl, (1R, 2S, 4R) -4, 6-trimethyl-bicyclo [3, 1] heptan-2-ol, tetrahydro-4-methyl-2-phenyl-2H-pyran (source: firmendich SA, switzerland), cyclohexyl acetate, trimethylcyclohexane acetate (source: firmendich SA, switzerland) 1, 8-p-menthen-7-ol (source: firmendich SA, switzerland) 1, 3RS, 4-p-menthen-4-ol, acetic acid (1 RS,3RS,4 SR) -3-p-menthyl (1, 2S), 4, 6-trimethyl-bicyclo [3, 1] heptan-2-ol, 1] methyl-2-ethyl-methyl (source: 7-R, 1-p-7-furanone (source: firmendich) and (source: firmendin), 2,4, 6-trimethyl-4-phenyl-1, 3-dioxane, 2,4, 6-trimethyl-3-cyclohexene-1-carbaldehyde;
-group 2: (E) -3-methyl-5- (2, 3-trimethyl-3-cyclopenten-1-yl) -4-penten-2-ol (source: givaudan SA, switzerland Wei Ernie), (1 'R, E) -2-ethyl-4- (2', 2',3' -trimethyl-3 '-cyclopenten-1' -yl) -2-buten-1-ol (source: firmendish SA, switzerland Nitro tile), (1 'R, E) -3, 3-dimethyl-5- (2', 2',3' -trimethyl-3 '-cyclopenten-1' yl) -4-penten-2-ol (source: firmendish SA, switzerland Nitro tile), 2-heptyl-cyclopentanone, methyl-cis-3-oxo-2-pentyl-1-cyclopentanecetate (source: firmendich SA, switzerland Nitro tile), 2-5-trimethyl-5-pentyl-1-cyclopentanone (source: firmendish SA), 3-dimethyl-5- (2 ',3' -cyclopenten-1-yl) -4-ol (source: givaudan SA, swiss Wei Ernie);
-group 3: a mixture of damascenone, 1- (5, 5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one (source: firmentich SA, switzerland geneva), 2- [2- (4 '-methyl-3' -cyclohexen-1 '-yl) propyl ] cyclopentanone, alpha-ionone, beta-ionone, damascenone, 1- (5, 5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one and 1- (3, 3-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one (source: firmentich SA, switzerland geneva), 1- (2, 6-trimethyl-1-cyclohexen-1-yl) -2-buten-1-one (source: firmentich SA, switzerland geneva), propionic acid (1S, 1' R) - [1- (3 ',3' -dimethyl-1 '-cyclohex-1' -oxycarbonyl ] methyl ester (source: firmentich SA), 7-butyl-1-hydroxy-1-ketone (source: firmentich SA), and 4-penten-1-one (source: firmentich SA, 6-trimethyl-1-cyclohexen-1-yl) -2-buten-1-one (source: firmentich SA, switzerland gener SA, trans-1- (2, 6-trimethyl-1-cyclohexyl) -3-hexanol (source: firmentich SA, switzerland geneva), (E) -3-methyl-4- (2, 6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one, terpene isobutyrate, 4- (1, 1-dimethylethyl) -1-cyclohexyl acetate (source: firmentich SA, switzerland geneva), 8-methoxy-1-p-menthene, propionic acid (1 s,1 'r) -2- [1- (3', 3 '-dimethyl-1' -cyclohexyl) ethoxy ] -2-methylpropyl propionate (source: firmentich SA, switzerland geneva), p-t-butylcyclohexanone, menthanethiol, 1-methyl-4- (4-methyl-3-pentenyl) -3-cyclohexene-1-carbaldehyde, allyl cyclohexylpropionate, cyclohexyl salicylate, 2-methoxy-4-methylphenyl methyl carbonate, 2-methoxy-4-methylphenyl carbonate, 4-methyl-phenyl carbonate, 4-methoxy-ethyl carbonate;
-group 4: methylcedrone (source: international Flavors and Fragrances, U.S.), 2-methylpropanoic acid (1 RS,2SR,6RS,7RS,8 SR) -tricyclo [5.2.1.0 2,6 ]Dec-3-en-8-yl ester (1 RS,2SR,6RS,7RS,8 SR) -tricyclo [5.2.1.0 2,6 ]Mixtures of dec-4-en-8-yl esters, vetiverol, vetiverone, 1- (octahydro-2, 3, 8-tetramethyl-2-naphthyl) -1-ethanone (origin: international Flavors and Fragrances, U.S. (5 RS,9RS,10 SR) -2,6,9,10-tetramethyl-1-oxaspiro [ 4.5)]Decyl-3, 6-diene and (5 RS,9SR,10 RS) isomers, 6-ethyl-2,10,10-trimethyl-1-oxaspiro [4.5 ]]Decyl-3, 6-diene, 1,2,3,5,6, 7-hexahydro-1, 2, 3-pentamethyl-4-indanone (source: international Flavors and Fragrances, U.S.), a mixture of 3- (3, 3-dimethyl-5-indanyl) propanal and 3- (1, 1-dimethyl-5-indanyl) propanal (source: firmencich SA, switzerland), 3', 4-dimethyl-tricyclo [6.2.1.0 (2, 7)]Undec-4-ene-9-spiro-2' -oxirane (source: firmenich SA, switzerland), 9/10-ethyldiene-3-oxatricyclo [6.2.1.0 (2, 7)]Undecane, (perhydro-5,5,8A-trimethyl-2-naphthyl acetate (source: firmelich SA, switzerland), 1-naphthol (octrynol), (dodecahydro-3 a,6, 9 a-tetramethylnaphtho [2,1-b ] ]Furan (origin: firmenich SA, switzerland), tricyclo acetate [5.2.1.0 (2, 6)]Dec-3-en-8-yl ester and tricyclo acetate [5.2.1.0 (2, 6)]Dec-4-en-8-yl esters and tricyclo [5.2.1.0 (2, 6) propionic acid]Dec-3-en-8-yl esters and tricyclo [ 5.2.1.0.propionic acid(2,6)]Dec-4-en-8-yl ester, (+) - (1S, 2S, 3S) -2, 6-trimethyl-bicyclo [3.1.1 ]]Heptane-3-spiro-2 '-cyclohexene-4' -one;
-group 5: camphor, borneol, isobornyl acetate, 8-isopropyl-6-methyl-bicyclo [2.2.2]Oct-5-ene-2-carbaldehyde, pinene, camphene, 8-methoxycedrane, (8-methoxy-2, 6, 8-tetramethyl-tricyclo [5.3.1.0 (1, 5))]Undecane (origin: firmenich SA, switzerland), cedrene, cedrol, 9-ethylene-3-oxatricyclo [6.2.1.0 (2, 7)]Undecan-4-one and 10-ethylene-3-oxatricyclo [6.2.1.0 ] 2,7 ]Mixtures of undecan-4-one (origin: firmenich SA, switzerland), 3-methoxy-7, 7-dimethyl-10-methylene-bicyclo [4.3.1 ]]Decane (origin: firmenich SA, switzerland);
-group 6: (trimethyl-13-oxabicyclo- [10.1.0] -tridecyl-4, 8-diene (source: firmencich SA, switzerland geneva), 9-hexadecene-16-lactone (source: firmencich SA, switzerland geneva), cyclopentadecanone (source: firmencich SA, switzerland geneva), 3-methyl (4/5) -cyclopentadecanone (source: firmencich SA, switzerland geneva), 3-methyl cyclopentadecanone (source: firmencich SA, switzerland geneva), pentadecanone (source: firmencich SA, switzerland geneva), (1-ethoxyethoxy) cyclododecane (source: firmencich SA, switzerland geneva), 1, 4-dioxaheptadecane-5, 17-dione, 4, 8-cyclododecene-1-one;
-group 7: (+ -) -2-methyl-3- [4- (2-methyl-2-propyl) phenyl ] propanal (origin: givaudan SA, switzerland Wei Ernie), acetic acid 2, 2-trichloro-1-phenylethyl ester.
Preferably, the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of the ingredients selected from groups 1 to 7 as defined above. More preferably, the perfume comprises at least 30%, preferably at least 50% of the ingredients selected from groups 3 to 7 as defined above. Most preferably, the perfume comprises at least 30%, preferably at least 50% of a component selected from group 3, group 4, group 6 or group 7 as defined above.
According to another preferred embodiment, the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients having a log p higher than 3, preferably higher than 3.5, even more preferably higher than 3.75.
According to a particular embodiment, the perfume used in the present invention contains less than 10% by weight of its own primary alcohol, less than 15% by weight of its own secondary alcohol and less than 20% by weight of its own tertiary alcohol. Advantageously, the perfume used in the present invention does not contain any primary alcohols, but less than 15% secondary and tertiary alcohols.
According to one embodiment, the oil phase (or oil-based core) comprises:
25 to 100 wt% of a perfume oil comprising at least 15 wt% of a high impact perfume raw material having a Log T < -4, and
0 to 75% by weight of a density-balancing material having a density of greater than 1.07g/cm 3 。
"high impact perfume raw material" is understood to be a perfume raw material of Log T < -4. The odor threshold concentration of a chemical compound is determined in part by its shape, polarity, partial charge, and molecular weight. For convenience, the odor threshold concentration is expressed as a common logarithm of the threshold concentration, i.e., log [ threshold ] ("Log").
"Density balance material" is understood to mean a density of greater than 1.07g/cm 3 And preferably has a low or odorless material.
The odor threshold concentration of the perfuming compounds was determined by using a gas chromatograph ("GC"). Specifically, the gas chromatograph is calibrated to determine the exact volume of the flavor oil component injected by the injector, the exact split ratio, and the hydrocarbon response using hydrocarbon standards of known concentration and chain length distribution. The air flow rate was accurately measured and the sample volume was calculated assuming a duration of human inhalation of 12 seconds. Since the exact concentration at any point in time at the detector is known, the mass per volume inhaled is known, so the concentration of the perfuming compound is known. To determine the threshold concentration, the solution is delivered to the sniffing port in a back-calculated concentration. Panelists sniff the GC effluent and determine the retention time at which the odor was perceived. The average of all panelists determined the odor threshold concentration of the flavoring compound. Determination of odor thresholds is described in more detail in c.v. uilleumier et al Multidimensional Visualization of Physical and Perceptual Data Leading to a Creative Approach in Fragrance Development, performe & flavor, vol.33, september, 2008, pages 54-61.
High impact perfume raw materials with Log T < -4 and with a perfume particle size of greater than 1.07g/cm are described in WO2018115250 3 The content of which is incorporated by reference.
According to one embodiment, log T<-4 is selected from the group consisting of: (+ -) -1-methoxy-3-hexanethiol, 4- (4-hydroxy-1-phenyl) -2-butanone, 2-methoxy-4- (1-propenyl) -1-phenyl acetate, pyrazolobutyl ether, 3-propylphenol, 1- (3-methyl-1-benzofuran-2-yl) ethanone, 2- (3-phenylpropyl) pyridine, 1- (3, 3/5, 5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one, 1- (5, 5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one, containing (3 RS,3aRS,6SR,7 ASR) -perhydro-3, 6-dimethyl-benzo [ B ]]Furan-2-one and (3 sr,3ars,6sr,7 asr) -perhydro-3, 6-dimethyl-benzo [ B ]]Mixtures of furan-2-one, (+ -) -1- (5-ethyl-5-methyl-1-cyclohexen-1-yl) -4-penten-1-one, (1 ' S,3' R) -1-methyl-2- [ (1 ',2',2' -trimethylbicyclo [ 3.1.0)]Hex-3' -yl) methyl]Cyclopropyl } methanol, acetic acid (+ -) -3-mercaptohexyl ester, (-) -1- (2, 6-trimethyl-1, 3-cyclohexadien-1-yl) -2-buten-1-one, H-methyl-2H-1, 5-benzodioxepin-3 (4H) -one, (2E, 6Z) -2, 6-nonadien-1-ol, (4Z) -4-dodecenal, (+ -4-hydroxy-2, 5-dimethyl-3 (2H) -furanone, methyl 2, 4-dihydroxy-3, 6-dimethylbenzoate, 3-methylindole, (+ -perhydro-4α, 8Abeta-dimethyl-4 a-naphthol, patchoulol, 2-methoxy-4- (1-propenyl) phenol, a mixture comprising (+) -5, 6-dihydro-4-methyl-2-phenyl-2H-pyran and tetrahydro-4-methylen-2H-pyran, a mixture comprising 4-hydroxy-2, 5-dimethyl-3 (2H) -furanone, 2, 4-dihydroxy-3-dimethylbenzene methyl-6-dimethylbenzene, 3-methylindole, (-) -perhydro-4α, 8A-dimethyl-4 a-naphthol, patchoulol, 2-methoxy-4- (1-propenyl) phenol, 3-methyl-5-phenyl-2-pentenenitrile, 1- (spiro [4.5 ] ]Dec-6/7-en-7-yl) -4-penten-1-one (-) - (3 aR,5AS,9 BR) -3a,6, 9 a-tetramethyldodecahydronaphtho[2,1-b]Furan, 5-nonolactone, (3 aR,5AS,9 BR) -3a,6, 9 a-tetramethyldodecahydronaphtho [2,1-b ]]Furan, 7-isopropyl-2 h,4h-1, 5-benzodioxepin-3-one, coumarin, 4-methylphenyl isobutyrate, (2E) -1- (2, 6-trimethyl-1, 3-cyclohexadien-1-yl) -2-buten-1-one, beta, 2, 3-tetramethyl-delta-methylen-3-cyclopenten-1-butanol, delta-damascenone ((2E) -1- [ (1 rs,2 sr) -2, 6-trimethyl-3-cyclohexen-1-yl]-2-buten-1-one), (+ -) -3, 6-dihydro-4, 6-dimethyl-2-phenyl-2 h-pyran, anisaldehyde, p-cresol, 3-ethoxy-4-hydroxybenzaldehyde, 2-aminobenzoic acid methyl ester, methyl phenyl glycidic acid ethyl ester, gamma-octalactone, 3-phenyl-2-acrylic acid ethyl ester, (-) - (2E) -2-ethyl-4- [ (1R) -2, 3-trimethyl-3-cyclopenten-1-yl]-2-buten-1-ol, p-cresol acetate, dodecalactone, dimethyltricyclo [7.1.1.0 ] 2,7 ]Undec-2-en-4-one (tricycloone), (+) - (3R, 5Z) -3-cyclopentadecen-1-one, undecalactone, (1R, 4R) -8-mercapto-3-p-menthone, (3S, 3AS,6R,7 AR) -3, 6-dimethylhexahydro-1-benzofuran-2 (3H) -one, beta-ionone, (+ -) -6-pentylthio-2H-pyran-2-one, (3E, 5Z) -1,3, 5-undecatriene, 10-undecenal, (9E) -9-undecenal, (9Z) -9-undecenal, (Z) -4-decenal, 2-methylpentanoic acid (-) -ethyl ester, 1, 2-diallyl disulfide, 2-tridecen nitrile, 3-tridecen nitrile, (-) -2-ethyl-4, 4-dimethyl-1, 3-oxathiolane, (+ -) -3-methyl-5-cyclopentadec-1-one, 3- (3E, 5Z) -3-methyl-pentadecen-1-one, 3- (4-tert-butyl) cyclopropene, 4-methyl-4-butan-one, and (4-methyl) - (-) -4-methyl-naphtalene (+ -) -5E 3-methyl-5-cyclopentadec-1-one, 3-hexenoic acid cyclopropylmethyl ester, (4E) -4-methyl-5- (4-methylphenyl) -4-pentenal, (+ -) -1- (5-propyl-1, 3-benzodioxol-2-yl) ethanone, 4-methyl-2-pentylpyridine, (+ - (E) -3-methyl-4- (2, 6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one, (3 aRS,5aSR,9 bRS) -3a,6, 9 a-tetramethyldodecahydronaphtho [2,1-b ]Furan, (2 s,5 r) -5-methyl-2- (2-propyl) cyclohexanone oxime, 6-hexyltetrahydro-2H-pyran-2-one, (+ -) -3- (3-isopropyl-1-phenyl) butanal, methyl 2- (3-oxo-2-pentylcyclopentyl) acetate, 1- (2, 6-trimethyl-1-cyclohex-2-enyl) pent-1-en-3-one, indole, 7-propyl-2H, 4H-1, 5-benzodioxanHept-3-one, ethyl maltol (ethyl praline), (4-methylphenoxy) acetaldehyde, tricyclo [5.2.1.0 ] (2, 6)]Decan-2-carboxylic acid ethyl ester, (+) - (1's, 2s, E) -3, 3-dimethyl-5- (2', 2',3' -trimethyl-3 '-cyclopenten-1' -yl) -4-penten-2-ol, (4E) -3, 3-dimethyl-5- [ (1R) -2, 3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 8-isopropyl-6-methyl-bicyclo [2.2.2]Oct-5-ene-2-carbaldehyde, methylnonylacetaldehyde, 4-formyl-2-methoxyphenyl 2-methylpropionate, (E) -4-decenal, (+ -) -2-ethyl-4- (2, 3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol, (1R, 5R) -4, 7-trimethyl-6-thiabicyclo [3.2.1]Oct-3-ene, (1R, 4R, 5R) -4, 7-trimethyl-6-thiabicyclo [3.2.1]Octane, (-) - (3R) -3, 7-dimethyl-1, 6-octadien-3-ol, (E) -3-phenyl-2-acrylonitrile, 4-methoxybenzyl acetate, (E) -3-methyl-5- (2, 3-trimethyl-3-cyclopenten-1-yl) -4-penten-2-ol, (2/3-methylbutoxy) allyl acetate, (+ - (2E) -1- (2, 6-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one, (1E) -1- (2, 6-trimethyl-1-cyclohexen-1-yl) -1-penten-3-one, and mixtures thereof.
According to one embodiment, the perfume raw material of Log T < -4 is selected from the group consisting of aldehydes, ketones, alcohols, phenols, esters, lactones, ethers, epoxides, nitriles and mixtures thereof.
According to one embodiment, the perfume raw material of Log T < -4 comprises at least one compound selected from the group consisting of alcohols, phenols, esters, lactones, ethers, epoxides, nitriles and mixtures thereof, preferably in an amount of 20 to 70% by weight, based on the total weight of the perfume raw material of Log T < -4.
According to one embodiment, the perfume raw material of LogT < -4 comprises 20-70% by weight aldehydes, ketones and mixtures thereof, based on the total weight of the perfume raw material of LogT < -4.
Thus, the remaining perfume raw materials contained in the oil-based core may have Log T > -4.
According to one embodiment, the perfume raw material of Log T > -4 is selected from the group consisting of: ethyl 2-methylbutanoate, acetic acid (E) -3-phenyl-2-propenoyl ester, (+ -) -6/8-sec-butylquinoline, (+ -) -3- (1, 3-benzodioxol-5-yl) -2-methylpropanoate, tricyclodecenyl propionate, 1- (octahydro-2, 3, 8-tetramethyl-2-naphthyl) -1-ethanone, methyl 2- ((1 rs,2 rs) -3-oxo-2-pentylcyclopentyl) acetate, (+ -) - (E) -4-methyl-3-decen-5-ol, 2, 4-dimethyl-3-cyclohexene-1-carbaldehyde 1, 3-trimethyl-2-oxabicyclo [2.2.2] octane, tetrahydro-4-methyl-2- (2-methyl-1-propenyl) -2H-pyran, dodecanal, 1-oxa-12-cyclohexadec-en-2-one, (+ -) -3- (4-isopropylphenyl) -2-methylpropanaldehyde, C11 aldehyde, (+ -) -2, 6-dimethyl-7-octen-2-ol, allyl 3-cyclohexylpropionate, (Z) -3-hexenyl acetate, 5-methyl-2- (2-n-propyl) cyclohexanone, allyl heptanoate, 2- (2-methyl-2-n-propyl) cyclohexyl acetate, 1-dimethyl-2-phenylethyl butyrate, geranyl acetate, neryl acetate, (+ -) -1-phenylethyl acetate, 1-dimethyl-2-phenylethyl acetate, 3-methyl-2-butenyl acetate, ethyl 3-oxobutyrate, 3-hydroxy-2-butenoic acid (2Z) -ethyl ester, 8-p-menthol, 8-p-menthyl acetate, 1-p-menthyl acetate, (+ -) -2- (4-methyl-3-cyclohexen-1-yl) -2-propyl acetate, (+ -) -2-methylbutyl propionate, 2- { (1S) -1- [ (1R) -3, 3-dimethylcyclohexyl ] ethoxy } -2-oxoethyl acetate, 3,5, 6-trimethyl-3-cyclohexene-1-carbaldehyde, 2,4, 6-trimethyl-3-cyclohexene-1-carbaldehyde, 2-cyclohexyl acetate, octyl aldehyde, ethyl butyrate, (-) -2- (4-methyl-3-cyclohexen-1-yl) -2-propyl butyrate, 2- [ (1R) -3, 3-dimethylcyclohexyl ] ethoxy } -2-oxoethyl propionate, 3, 6-trimethyl-3-cyclohexen-1-carbaldehyde, 1, 3-trimethyl-2-oxabicyclo [2.2.2] octane, ethyl caproate, undecalaldehyde, decanal, 2-phenylethyl acetate, (1S, 2S, 4S) -1, 7-trimethylbicyclo [2.2.1] heptan-2-ol, (1S, 2R, 4S) -1, 7-trimethylbicyclo [2.2.1] heptan-2-ol), (+ -) -3, 7-dimethyl-3-octanol, 1-methyl-4- (2-propanylidene) cyclohexene (+) - (R) -4- (2-methoxypropan-2-yl) -1-methylcyclohex-1-ene, tricyclodecenyl acetate, (3R) -1- [ (1R, 6S) -2, 6-trimethylcyclohexyl ] -3-hexanol, (3S) -1- [ (1R, 6S) -2, 6-trimethylcyclohexyl ] -3-hexanol, (3R) -1- [ (1S, 6S) -2, 6-trimethylcyclohexyl ] -3-hexanol, propionic acid (+) - (1S, 1 'R) -2- [1- (3', 3 '-dimethyl-1' -cyclohexyl) ethoxy ] -2-methylpropyl ester, and mixtures thereof.
According to one embodiment, the core comprises a perfume formulation comprising:
0 to 60 wt% of a hydrophobic solvent (based on the total weight of the perfume formulation),
40 to 100 wt% of a perfume oil (based on the total weight of the perfume formulation), wherein the perfume oil has at least two, preferably all, of the following properties:
at least 35%, preferably 40%, preferably at least 50%, more preferably at least 60% of the perfuming ingredients have a log P of greater than 3, preferably greater than 3.5,
at least 20%, preferably 25%, preferably at least 30%, more preferably at least 40% of a large steric hindrance (bulk) material of groups 1 to 6, preferably groups 3 to 6, as defined previously, and
at least 15%, preferably at least 20%, more preferably at least 25%, even more preferably at least 30% of Log T < -4 of the high impact perfume material as defined previously,
-optionally, a further hydrophobic active ingredient.
According to a particular embodiment, the perfume comprises 0 to 60% by weight of hydrophobic solvent.
According to a particular embodiment, the hydrophobic solvent is a density balancing material, preferably selected from the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenyl ethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylates, benzyl cinnamate, and mixtures thereof.
In a particular embodiment, the hydrophobic solvent has a hansen solubility parameter compatible with the embedded (engineered) perfume oil.
The term "Hansen solubility parameter" is understood to mean the solubility parameter method proposed by Charles Hansen (Charles Hansen) for predicting the solubility of polymers and developed on the basis of the total vaporization energy of a liquid consisting of several individual parts. To calculate the "weighted hansen solubility parameter", the effects of (atomic) dispersion forces, (molecular) permanent dipole-permanent dipole forces and (molecular) hydrogen bonding (electron exchange) must be combined. Weighted hansen solubility parameter calculationIs (delta D) 2 +δP 2 +δH 2 ) 0.5 Where δd is hansen dispersion value (hereinafter also referred to as atomic dispersion force), δp is hansen polarization value (hereinafter also referred to as dipole moment), and δh is hansen hydrogen bond ("H-bond") value (hereinafter also referred to as hydrogen bond). For a more detailed description of this parameter and this value, see Charles Hansen The Three Dimensional Solubility Parameter and Solvent Diffusion Coefficient, danish Technical Press (Copenhagen, 1967).
The euclidean difference in the solubility parameters of the fragrance and the solvent was calculated as (4 x (δd solvent -δD fragrance ) 2 +(δP solvent -δP fragrance ) 2 +(δH solvent -δH fragrance ) 2 ) 0.5 Wherein δD solvent 、δP solvent And delta H solvent The hansen dispersion value, hansen polarization value and hansen hydrogen bond value of the solvent respectively; and delta D fragrance 、δ fragrance And delta H fragrance Hansen dispersion values, hansen polarization values, and hansen hydrogen bond values, respectively, for fragrances.
In a particular embodiment, the perfume oil and the hydrophobic solvent have at least two hansen solubility parameters selected from the first group consisting of: atomic dispersion forces (δd) of 12 to 20, dipole moments (δp) of 1 to 8, and hydrogen bonds (δh) of 2.5 to 11.
In a particular embodiment, the perfume oil and the hydrophobic solvent have at least two hansen solubility parameters selected from the second group consisting of: an atomic dispersion force (δd) of 12 to 20, preferably 14 to 20, a dipole moment (δp) of 1 to 8, preferably 1 to 7, and a hydrogen bond (δh) of 2.5 to 11, preferably 4 to 11.
In a particular embodiment, at least 90% of the perfume oil, preferably at least 95% of the perfume oil, most preferably at least 98% of the perfume oil has at least two hansen solubility parameters selected from the first group consisting of: atomic dispersion forces (δd) of 12 to 20, dipole moments (δp) of 1 to 8, and hydrogen bonds (δh) of 2.5 to 11.
In a particular embodiment, the perfume oil and the hydrophobic solvent have at least two hansen solubility parameters selected from the second group consisting of: an atomic dispersion force (δd) of 12 to 20, preferably 14 to 20, a dipole moment (δp) of 1 to 8, preferably 1 to 7, and a hydrogen bond (δh) of 2.5 to 11, preferably 4 to 11.
According to one embodiment, the perfuming formulation comprises a fragrance modulator (which may be used together with a hydrophobic solvent when present, or as a substitute for a hydrophobic solvent when not present).
Preferably, the fragrance modulator is defined as a fragrance material having:
i. a vapor pressure of less than 0.0008Torr at 22 ℃;
a clogP of 3.5 or more, preferably 4.0 or more, more preferably 4.5;
at least two hansen solubility parameters selected from a first group consisting of: atomic dispersion forces of 12 to 20, dipole moments of 1 to 7 and hydrogen bonds of 2.5 to 11,
at least two hansen solubility parameters selected from a second group consisting of: atomic dispersion forces of 14 to 20, dipole moments of 1 to 8, hydrogen bonds of 4 to 11 when in solution with compounds having vapor pressures in the range of 0.0008to 0.08Torr at 22 ℃.
Preferably, as examples, the following ingredients may be listed as modulators, but the list is not limited to the following: alcohol C12, oxacyclohexadec-12/13-en-2-one, 3- [ (2 ',3' -trimethyl-3 ' -cyclopenten-1 ' -yl) methoxy ] -2-butanol, cyclohexadecone, (Z) -4-cyclopentadecen-1-one, cyclopentadecone, (8Z) -oxacyclohexadec-8-en-2-one, 2- [5- (tetrahydro-5-methyl-5-vinyl-2-furyl) -tetrahydro-5-methyl-2-furyl ] -2-propanol, convalal, 1,5, 8-trimethyl-13-oxabicyclo [10.1.0] tridec-4, 8-diene (+ -) -4,6, 7, 8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta [ g ] isochroman, (+) - (1S, 2S,3S, 5R) -2, 6-trimethylspiro [ bicyclo [3.1.1] heptane-3, 1' -cyclohexane ] -2' -en-4 ' -one, oxacyclohexan-2-one, propionic acid 2- { (1S) -1- [ (1R) -3, 3-dimethylcyclohexyl ] ethoxy } -2-oxoethyl ester, (+) - (4R, 4aS, 6R) -4,4 a-dimethyl-6- (1-propen-2-yl) -4,4a,5,6,7, 8-hexahydro-2 (3H) -naphthalenone, amyl cinnamic aldehyde, hexyl salicylate, (1E) -1- (2, 6-trimethyl-1-cyclohexen-1-yl) -1, 6-heptadien-3-one, (9Z) -9-cycloheptadecen-1-one.
According to a particular embodiment, the hydrophobic material is free of any active ingredient (e.g. perfume). According to this particular embodiment, it comprises, preferably consists of, a hydrophobic solvent, preferably selected from isopropyl myristate, triglycerides (e.g.,MCT oil, vegetable oil), D-limonene, silicone oil, mineral oil and mixtures thereof, and optionally a hydrophilic solvent preferably selected from the group consisting of: 1, 4-butanediol, benzyl alcohol, triethyl citrate, triacetin, benzyl acetate, ethyl acetate, propylene glycol (1, 2-propanediol), 1, 3-propanediol, dipropylene glycol, glycerol, glycol ethers, and mixtures thereof.
The term "biocide" refers to a chemical substance that is capable of killing living organisms (e.g., microorganisms) or reducing or preventing their growth and/or accumulation. Biocides are commonly used in medicine, agriculture, forestry and industry to prevent scaling of, for example, water, agricultural products (including seeds) and oil pipelines. The biocide may be a pesticide, including fungicides, herbicides, insecticides, algicides, molluscicides, miticides, and rodenticides; and/or antimicrobial agents, such as bactericides, antibiotics, antibacterial agents, antiviral agents, antifungal agents, antiprotozoal agents, and/or antiparasitic agents.
As used herein, a "pest control agent" refers to a substance that is used to repel or attract a pest to reduce, inhibit or promote its growth, development or activity. By pest is meant any organism, whether animal, plant or fungus, that is invasive or troublesome to plants or animals, including insects, especially arthropods, mites, arachnids, fungi, weeds, bacteria and other microorganisms.
By "flavor oil", it is meant herein a flavoring ingredient, or a mixture of flavoring ingredients, solvents or adjuvants currently used in the preparation of flavoring formulations, i.e., a specific mixture of ingredients intended to be added to an edible composition or chewing product to impart, improve or modify its organoleptic properties, in particular its flavor and/or taste. Flavoring ingredients are well known to those skilled in the art and their nature does not warrant a more detailed description here, which in any case would not be exhaustive, the skilled flavoring agent being able to choose them according to its general knowledge and to the intended use or application and the organoleptic effect that it is desired to achieve. Many of these flavoring ingredients are listed in the references, for example, book Perfume and Flavor Chemicals,1969, montclair, N.J., USA or its latest version, or other works of similar nature, such as Fenaroli's Handbook of Flavor Ingredients,1975, CRC Press or Synthetic Food Adjuncts,1947,van Nostrand Co of M.B. Jacobs, inc. Solvents and adjuvants currently used in the preparation of flavoring formulations are also well known in the art.
In a particular embodiment, the flavoring is peppermint flavoring. In a more specific embodiment, the mint is selected from the group consisting of peppermint (peppermint) and spearmint (spearmint).
In a further embodiment, the flavoring agent is a cooling agent or a mixture thereof.
In another embodiment, the flavoring is menthol flavoring.
Flavoring agents derived from or based on fruit (in which citric acid is the predominant naturally occurring acid) include, but are not limited to, for example, citrus fruit (e.g., lemon, lime), limonene, strawberry, orange, and pineapple. In one embodiment, the flavoring food is lemon juice, lime juice, or orange juice extracted directly from fruit. Other embodiments of the flavoring agents include juices or liquids extracted from orange, lemon, grapefruit, lime, citron, citrus parvos (clementins), mandarin (mannirins), mandarin (tangerines), and any other citrus fruit or variety or hybrid thereof. In a particular embodiment, the flavoring agent comprises a liquid extracted or distilled from orange, lemon, grapefruit, lime, citron, citrus parviflora, orange, tangerine, any other citrus fruit or variety or hybrid thereof, pomegranate, kiwi, watermelon, apple, banana, blueberry, melon, ginger, sweet pepper, cucumber, passion fruit, mango, pear, tomato, and strawberry.
In a particular embodiment, the flavoring agent comprises a limonene containing composition. In a particular embodiment, the composition is citrus further comprising limonene.
In another particular embodiment, the flavor comprises a flavor selected from the group consisting of strawberry, orange, lime, tropical fruit, berry mixture, and pineapple.
The phrase flavor includes not only flavors that impart or modify the odor of food, but also ingredients that impart or modify the taste. The latter does not necessarily have a taste or smell per se, but can improve the taste provided by other ingredients such as a salty taste enhancing ingredient, a sweet taste enhancing ingredient, a umami taste enhancing ingredient, a bitter taste blocking ingredient, etc.
In further embodiments, suitable sweetening components may be included in the particles described herein. In a particular embodiment, the sweetening component is selected from the group consisting of sugar (e.g., without limitation sucrose), stevia component (e.g., without limitation stevioside or rebaudioside a), sodium cyclamate (cyclamate), aspartame, sucralose, sodium saccharin, and potassium acesulfame, or mixtures thereof.
Polymer shell
According to one embodiment, the polymeric shell comprises a material selected from the group consisting of polyamides, polyureas, polyurethanes, polyesters, polyacrylates, polysiloxanes, polycarbonates, polysulfonamides, urea-formaldehyde polymers, melamine-urea polymers, or melamine-glyoxal polymers, and mixtures thereof.
According to a particular embodiment, the polymeric (poly) material is a polyamide.
According to a particular embodiment, the polyamide material is obtained from the reaction between an acyl chloride and at least one amino compound, i.e. at least one amino compound a, such as Ethylenediamine (EDA).
According to a particular embodiment, the polyamide material is obtained from the reaction between an acyl chloride and at least two amino compounds, i.e. at least one amino compound a and at least one amino compound B, for example L-lysine and Ethylenediamine (EDA).
According to a particular embodiment, the polyamide is obtained from the reaction between an acid chloride and at least three amino compounds, i.e. at least one amino compound a, at least one amino compound B and at least one amino compound C, such as L-lysine, ethylenediamine (EDA) and Diethylenetriamine (DETA).
The amino compound (a and/or B and/or C) may be selected from the group consisting of: cystamine, cystamine hydrochloride, cystine hydrochloride, cystine dialkyl ester hydrochloride, m-xylylene diamine, 1, 2-diaminocyclohexane, 1, 4-diaminocyclohexane, polyetheramine, ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris- (2-aminoethyl) amine, 3-aminopropyl triethoxysilane, 1, 4-diaminobutane, 2-dimethyl-1, 3-propylenediamine, 1, 3-diaminopentane (Dytek EP diamine), 1, 2-diaminopropane, triethylenetetramine, 1, 3-diaminopropane; urea; ethylene urea; aminoguanidine bicarbonate; 1- (2-aminoethyl) imidazolin-2-one; n- (3-aminopropyl) -N-dodecylpropane-1, 3-diamine; n1- (2-aminoethyl) -N1-dodecyl-1, 2-ethylenediamine; aminoethylethanolamine; n1- (3-aminopropyl) propane-1, 3-diamine, polyethylenimine, amino acids such as L-lysine, L-arginine, L-histidine, L-tryptophan, L-serine, L-glutamine, L-threonine, L-leucine, and/or oligomers and polymers derived therefrom, and mixtures thereof.
According to a particular embodiment, the at least one amino compound is an amino acid, preferably selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan, L-serine, L-glutamine, L-threonine, L-leucine and mixtures thereof.
According to one embodiment, the amino compound (a and/or B and/or C) is selected from the group consisting of: m-xylylenediamine, 1, 2-diaminocyclohexane, 1, 4-diaminocyclohexane, L-lysine ethyl ester and polyetheramineEthylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris- (2-aminoethyl) amine, 3-aminopropyl triethoxysilane, L-arginine, 1, 4-diaminobutane, 2-dimethyl-1, 3-propanediamine, 1, 3-diaminopentane (Dytek EP diamine), 1, 2-diaminopropane, triethylenetetramine, amines having disulfide bonds such as cystamine, cystamine hydrochloride, cystine hydrochloride, cystine dialkyl esters, cystine dialkyl ester hydrochloride, and mixtures thereof.
According to a particular embodiment, the acid chloride corresponds to the following formula (I):
wherein n is an integer from 1 to 8, preferably from 1 to 6, more preferably from 1 to 4, and
Wherein X is C of (n+1) valence 2 To C 45 A hydrocarbon group, optionally comprising at least one group selected from (i) to (xi), in particular from (i) to (vi),
wherein R is a hydrogen atom or an alkyl group such as methyl or ethyl, preferably a hydrogen atom.
It will be appreciated that by "… hydrocarbyl …" it is meant that the groups are composed of hydrogen and carbon atoms and may be in the form of aliphatic hydrocarbons, i.e., straight or branched chain saturated hydrocarbons (e.g., alkyl groups), straight or branched chain unsaturated hydrocarbons (e.g., alkenyl or alkynyl groups), saturated cyclic hydrocarbons (e.g., cycloalkyl groups) or unsaturated cyclic hydrocarbons (e.g., cycloalkenyl or cycloalkynyl groups), or may be in the form of aromatic hydrocarbons, i.e., aryl groups, or may also be in the form of mixtures of groups of the types, e.g., a particular group may contain straight chain alkyl, branched alkenyl (e.g., having one or more carbon-carbon double bonds), (poly) cycloalkyl groups, and aryl moieties unless specifically limited to only one of the types mentioned. Similarly, in all embodiments of the invention, when referring to a group as being of more than one type of topology (e.g., linear, cyclic, or branched) and/or saturated or unsaturated (e.g., alkyl, aromatic, or alkenyl) form, it is also meant that a group may comprise a moiety having any of the topologies or saturated or unsaturated as explained above. Similarly, in all embodiments of the invention, when referring to a group as being in one form saturated or unsaturated (e.g., alkyl), it is meant that the group may be of any type of topology (e.g., linear, cyclic, or branched) or have several moieties with various topologies.
It should be understood that the term "… hydrocarbyl, optionally containing …" means that the hydrocarbyl optionally contains heteroatoms to form ether, thioether, amine, nitrile, or carboxylic acid groups and derivatives (including, for example, esters, acids, amides). These groups may replace the hydrogen atom of the hydrocarbon group and thus be pendant to the hydrocarbon, or replace the carbon atom of the hydrocarbon group (if chemically possible) and thus be inserted into the hydrocarbon chain or ring.
According to a particular embodiment, the acid chloride is selected from the group consisting of: benzene-1, 3, 5-triacyltrichloro (trimellitic acid chloride), benzene-1, 2, 4-triacyltrichloro, benzene-1, 2,4, 5-tetraacyltetraoyl tetracloride, cyclohexane-1, 3, 5-triacyltrichloro, isophthaloyl dichloride, diacetyl dichloride (diglycolyl dichloride) oxide, terephthaloyl dichloride, fumaroyl dichloride, adipoyl chloride, succinyl dichloride, propane-1, 2, 3-triacyltrichloro, cyclohexane-1, 2,4, 5-tetraacyltetracloride, 2' -disulfanediyldisuccinidichloride, 2- (2-chloro-2-oxoethyl) thiobutane diacid dichloride (4-chloro-4-oxobutanoyl) -L-glutamyl dichloride, (S) -4- ((1, 5-dichloro-1, 5-dioxopent-2-yl) amino) -4-oxobutanoic acid 2, 2-bis [ (4-chloro-4-oxo-butanoyl) oxymethyl ] butyl 4-chloro-4-oxo-butanoic acid [2- [2, 2-bis [ (4-chloro-4-oxo-butanoyl) oxymethyl ] butoxymethyl ] -2- [ (4-chloro-4-oxo-butanoyl) oxymethyl ] butyl ] ester 2, 2-chlorocarbonylbenzoic acid 2-bis [ (2-chlorocarbonylbenzoyl) oxymethyl ] butyl, 2- [2, 2-bis [ (2-chlorocarbonylbenzoyl) oxymethyl ] butoxymethyl ] -2- [ (2-chlorocarbonylbenzoyl) oxymethyl ] butyl ] 2,4, 5-trichlorocarbonyl-benzoic acid 4- (2, 4, 5-trichlorocarbonylbenzoyl) oxybutyl ester, propane-1, 2, 3-triyl tris (4-chloro-4-oxobutanoate), propane-1, 2-diyl bis (4-chloro-4-oxobutanoate) and mixtures thereof.
According to a particular embodiment, the acid chloride is selected from the group consisting of: benzene-1, 2, 4-triacyltrichloro, benzene-1, 2,4, 5-tetraacyltetrachloro, cyclohexane-1, 3, 5-triacyltrichloro, isophthaloyl dichloride, diacetyl dichloride oxide, terephthaloyl dichloride, fumaroyl dichloride, adipoyl dichloride, succinyl dichloride, propane-1, 2, 3-triacyltrichloro, cyclohexane-1, 2,4, 5-tetraacyltetrachloro, 2' -disulfanediyldisuccinyl dichloride, 2- (2-chloro-2-oxoethyl) thiobutanediyl dichloride, (4-chloro-4-oxobutanoyl) -L-glutamyl dichloride (S) -4- ((1, 5-dichloro-1, 5-dioxopent-2-yl) amino) -4-oxobutanoic acid, 4-chloro-4-oxo-butanoic acid 2, 2-bis [ (4-chloro-4-oxo-butanoyl) oxymethyl ] butyl ester, 4-chloro-4-oxo-butanoic acid [2- [2, 2-bis [ (4-chloro-4-oxo-butanoyl) oxymethyl ] butoxymethyl ] -2- [ (4-chloro-4-oxo-butanoyl) oxymethyl ] butyl ] ester, 2-bis [ (2-chlorocarbonylbenzoyl) oxymethyl ] butyl 2-chlorocarbonylbenzoic acid, 2- [2, 2-bis [ (2-chlorocarbonylbenzoyl) oxymethyl ] butoxymethyl ] -2- [ (2-chlorocarbonylbenzoyl) oxymethyl ] butyl ] ester of 2-chlorocarbonylbenzoic acid, 4- (2, 4, 5-trichlorocarbonylbenzoyl) oxybutyl ester of 2,4, 5-trichlorocarbonylbenzoic acid, propane-1, 2, 3-triyl tris (4-chloro-4-oxobutanoate), propane-1, 2-diyl bis (4-chloro-4-oxobutanoate) and mixtures thereof.
According to another particular embodiment, the acid chloride is selected from the group consisting of fumaroyl dichloride, adipoyl dichloride, succinyl dichloride, tris (4-chloro-4-oxobutanoic acid) propane-1, 2, 3-triyl ester, bis (4-chloro-4-oxobutanoic acid) propane-1, 2-diyl ester and mixtures thereof.
According to one embodiment, the acid chloride is a mixture of a plurality of acid chlorides.
The weight ratio between the acid chloride and the hydrophobic material is preferably 0.01 to 0.09, more preferably 0.02 to 0.07.
According to a particular embodiment, the acid chloride is used in an amount of 1.7 to 7 wt%, preferably 2.5 to 5 wt%, based on the total weight of the hydrophobic material.
According to a specific embodiment, the protein is selected from the group consisting of potato protein, chickpea protein, pea protein and mixtures thereof.
According to a particular embodiment, the core-shell microcapsule comprises:
a core comprising a hydrophobic material, preferably a perfume oil, and
-a polyamide shell comprising the reaction product between an acyl chloride and at least two amino compounds, preferably L-lysine and ethylenediamine, wherein the polyamide shell comprises potato protein.
According to a particular embodiment, the core-shell microcapsule comprises:
A core comprising a hydrophobic material, preferably a perfume oil, and
-a polyamide shell comprising the reaction product between an acyl chloride and at least two amino compounds, preferably L-lysine and ethylenediamine, wherein the polyamide shell comprises chickpea protein.
According to a particular embodiment, the core-shell microcapsule comprises:
a core comprising a hydrophobic material, preferably a perfume oil, and
-a polyamide shell comprising the reaction product between an acyl chloride and at least two amino compounds, preferably L-lysine and ethylenediamine, wherein the polyamide shell comprises pea protein.
The polyamide shell may comprise the reaction product of an acid chloride with at least three amino compounds, preferably L-lysine, ethylenediamine and ethylenediamine.
Another object of the present invention is a polyamide based core-shell microcapsule or polyamide based core-shell microcapsule slurry comprising at least one microcapsule comprising:
a core comprising a hydrophobic material, preferably a perfume, and
-a polyamide-based shell comprising the reaction product of:
acid chloride in an amount of 5% to 98%, preferably 20% to 98%, more preferably 30% to 85% w/w;
amino compound A in an amount of 1% to 50% w/w, preferably 7% to 40% w/w;
Alternatively, the amount of amino compound B is 1% to 50% w/w, preferably 2% to 25% w/w;
alternatively, the amount of amino compound C is 1% to 50% w/w, preferably 2% to 25% w/w;
proteins selected from the group consisting of potato protein, chickpea protein, pea protein, algae protein, fava bean protein, barley protein, oat protein, wheat gluten protein, lupin protein and mixtures thereof in an amount of 0.1% to 90% w/w, preferably 0.1% to 75% w/w, more preferably 1% to 70% w/w,
the above amounts are based on the total weight of the shell.
According to another embodiment, the polyamide-based shell comprises the reaction product of:
acid chloride in an amount of 5% to 98%, preferably 5% to 40%, more preferably 5% to 30% w/w;
amino compound A in an amount of 1% to 50% w/w, preferably 7% to 40% w/w;
alternatively, the amount of amino compound B is 1% to 50% w/w, preferably 2% to 25% w/w;
alternatively, the amount of amino compound C is 1% to 50% w/w, preferably 2% to 25% w/w;
proteins selected from the group consisting of potato protein, chickpea protein, pea protein, algae protein, fava bean protein, barley protein, oat protein, wheat gluten protein, lupin protein and mixtures thereof in an amount of 0.1% to 90% w/w, preferably 0.1% to 75% w/w, more preferably 1% to 70% w/w,
The above amounts are based on the total weight of the shell.
According to one embodiment, the shell comprises protein in an amount of 1% w/w to 80% w/w, more preferably 10% w/w to 75% w/w, even more preferably 30% w/w to 70% w/w, based on the total weight of the shell.
In a particular embodiment, the shell material is a biodegradable material.
In a particular embodiment, the shell is at least 40%, preferably at least 45%, 50%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% according to the biodegradability (bisodegradability) of OECD301F over 60 days.
In a particular embodiment, the core-shell microcapsules have a biodegradability of at least 40%, preferably at least 60%, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% over 60 days according to OECD 301F.
It will thus be appreciated that the core-shell microcapsules comprising all components such as core, shell and optionally coating may be at least 40%, preferably at least 60%, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% biodegradable over 60 days according to OECD 301F.
In a particular embodiment, the oil core, preferably a perfume oil, has a biodegradability of at least 40%, preferably at least 60%, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% over 60 days according to OECD 301F.
OECD301F is a standard test method for biodegradability by the economic co-ordination and development organization.
Gasparini and all in Molecules 2020,25,718 discloses a typical method for extracting the shell to measure biodegradability.
In a particular embodiment, the stability or chemical stability of the microcapsules is not more than 50%, preferably not more than 40%, preferably not more than 35%, preferably more than 30%. In general, the stability or chemical stability of the microcapsules is determined as that the microcapsules are stable after storage in a fabric softener, liquid detergent, body wash, body fragrance or antiperspirant for 15 days at 37 ℃, more preferably 30 days at 37 ℃, and are stable for at least 2 weeks at 40 ℃ in body emulsions (body emulsions), shampoos or hair conditioners, when incorporated into consumer products for a specific storage time and temperature, the perfume being not more than 50%, preferably not more than 40%, preferably not more than 35%, preferably not more than 30% released from the microcapsules.
Furthermore, the microcapsules preferably show a detectable friction effect on fresh samples, and preferably after 15 days of application storage at 37 ℃, even more preferably after 30 days at 37 ℃.
Proteins
The protein used in the present invention is a plant protein or a plant-based protein. "plant proteins" or "plant-based proteins" are used indifferently in the present invention. The protein is selected from the group consisting of potato protein, chickpea protein, pea protein, algae protein, fava bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof.
Patatin is typically extracted from potato tubers (Solanum tuberosum). According to one embodiment, the patatin is a native patatin and preferably comprises or consists of patatin.
According to one embodiment, the protein preferably has a solubility of greater than 10% potato protein. According to one embodiment, the protein preferably has a solubility of greater than 20% potato protein. According to one embodiment, the protein preferably has a solubility of greater than 30% of potato protein. According to one embodiment, the protein preferably has a solubility of greater than 40% potato protein. According to one embodiment, the protein preferably has a solubility of greater than 50% potato protein. According to one embodiment, the protein preferably has a solubility of greater than 60% potato protein. According to one embodiment, the protein preferably has a solubility of greater than 70% potato protein. According to one embodiment, the protein preferably has a solubility of greater than 80% potato protein. According to one embodiment, the protein preferably has a solubility of greater than 90% of potato protein. The above-mentioned solubility is given in water at room temperature (typically 20 ℃) and preferably at natural pH.
The proteins used in the present invention may be native, partially or fully denatured by any suitable method. Denaturation is a process by which the conformational structure of a protein is altered by unfolding, i.e. it involves the disruption and possible destruction of the secondary and tertiary structure of the protein. Indeed, denaturation means the cleavage of many weak links or bonds (e.g. hydrogen bonds) within a protein molecule responsible for the highly ordered structure of the protein in its natural state. Denaturation is reversible (proteins can resume their native state when the effect of denaturation is eliminated) or irreversible.
Denaturation can be achieved in a variety of ways. Proteins may be treated with oxidizing or reducing agents, inorganic salts, certain organic solvents, chaotropic agents (i.e., kJ Kg with positive chaotropic values-Hallsworth scale) due to exposure to temperature, radiation or mechanical stress (including shear), pH changes (treatment with alkali or acid) -1 Molar-compounds such as guanidine salts, e.g., guanidine carbonate, guanidine hydrochloride, urea, calcium chloride, n-butanol, ethanol, lithium perchlorate, lithium acetate, magnesium chloride, phenol, 2-propanol, sodium lauryl sulfate, thiourea).
Proteins used in the present invention may also be derivatized or modified (e.g., derivatized or chemically modified). For example, proteins may be modified by covalent attachment of a sugar, lipid, peptide or chemical group such as phosphate or methyl.
According to one embodiment, the presence or absence of salt (e.g., caCl 2 Or NaCl) by heat treatment (typically about 90 ℃).
Outer coating layer
According to a particular embodiment of the invention, the microcapsule comprises an outer coating layer (coating), wherein the outer coating layer comprises a polymer selected from the group consisting of nonionic polysaccharides, cationic polymers, polysuccinimide derivatives (as described in e.g. WO 2021185724) and mixtures thereof to form the outer coating layer of the microcapsule.
Nonionic polysaccharide polymers are well known to the person skilled in the art and are described, for example, in WO2012/007438, page 29, lines 1 to 25 and WO2013/026657, page 2, lines 12 to 19 and page 4, lines 3 to 12. The preferred nonionic polysaccharide is selected from the group consisting of locust bean gum, xyloglucan, guar gum, hydroxypropyl guar, hydroxypropyl cellulose, and hydroxypropyl methylcellulose.
Cationic polymers are well known to those skilled in the art. Preferred cationic polymers have a cationic charge density of at least 0.5meq/g, more preferably at least about 1.5meq/g, but also preferably less than about 7meq/g, more preferably less than about 6.2meq/g. The cationic charge density of the cationic polymer can be determined by the Kjeldahl method (Kjeldahl method) as described in the united states pharmacopeia in chemical tests for nitrogen determination. Preferred cationic polymers are selected from those containing primary, secondary, tertiary and/or quaternary amine groups, which may form part of the main polymer chain or may be carried by side substituents directly attached thereto. The weight average molecular weight (Mw) of the cationic polymer is preferably 10,000 to 3.5M daltons, more preferably 50,000 to 1.5M daltons. According to a particular embodiment, cationic polymers based on acrylamide, methacrylamide, N-vinylpyrrolidone, quaternized N, N-dimethylaminomethacrylate, diallyldimethylammonium chloride, quaternized vinylimidazole (3-methyl-1-vinyl-1H-imidazol-3-ium chloride), vinylpyrrolidone, acrylamidopropyltrimethylammonium chloride, cassia hydroxypropyl trimethylammonium chloride, guar hydroxypropyl trimethylammonium chloride or polygalactomannan 2-hydroxypropyl trimethylammonium chloride ether, starch hydroxypropyl trimethylammonium chloride and cellulose hydroxypropyl trimethylammonium chloride will be used. Preferably, the copolymer should be prepared from polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium 10, polyquaternium-11, polyquaternium-16, polyquaternium-22, polyquaternium-28, polyquaternium-43, polyquaternium-44, polyquaternium-46, cassia seed hydroxypropyl trimethyl ammonium chloride, guar gum hydroxypropyl trimethyl ammonium chloride or polygalactomannan 2-hydroxypropyl trimethyl ammonium chloride ether, starch hydroxypropyl trimethyl ammonium chloride and cellulose hydroxypropyl trimethyl ammonium chloride And (3) selecting from the group consisting of ammonium chloride. As specific examples of the commercially available products, there may be mentionedSC60 (cationic copolymer of acrylamide propyl trimethyl ammonium chloride and acrylamide, source: BASF) or +.>Such as PQ 11N, FC 550 or Style (Polyquaternised-11-68 or vinylpyrrolidone quaternized copolymer, source: BASF), or +.>(C13S or C17, source: rhodia).
According to any of the above embodiments of the invention, the amount of the above polymer added is about 0% to 5% w/w, or even about 0.1% to 2% w/w, the percentages being expressed on a w/w basis relative to the total weight of the slurry. It is well understood by those skilled in the art that only a portion of the added polymer will be incorporated/deposited on the microcapsule shell.
According to a particular embodiment, the microcapsules of the invention comprise a mineral layer. The mineral layer preferably comprises a material selected from the group consisting of iron oxide, iron oxyhydroxide, titanium oxide, zinc oxide, calcium carbonate, calcium phosphate, barium salts, strontium salts, magnesium salts, and mixtures thereof.
Optional ingredients
When the microcapsules are in the form of a slurry, the microcapsule slurry may comprise an adjunct ingredient selected from the group consisting of thickeners/rheology modifiers, biocides, opacity enhancers, mica particles, salts, pH stabilizers/buffering ingredients, preferably in an amount of 0 to 15 weight percent based on the total weight of the slurry.
According to another embodiment, the microcapsule slurry of the invention comprises additional free (i.e. unencapsulated) perfume, preferably in an amount of from 5 to 50 wt.% based on the total weight of the slurry.
Solid particles
Another object of the present invention is a solid particle comprising:
-a carrier material, preferably a polymeric carrier material selected from the group consisting of polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, vegetable gums, pectins, xanthans, alginates, carrageenans, cellulose derivatives and mixtures thereof, and
-microcapsules as defined above embedded in said carrier material, and
-optionally, free perfume embedded in the carrier material.
Solid particles and microcapsule powders as defined above are used indifferently in the present invention.
Method for preparing microcapsule slurry
Another object of the present invention is a method for preparing a core-shell microcapsule slurry comprising the steps of:
a) Preparing an oil phase comprising a hydrophobic material, preferably a perfume, to form an oil phase;
b) Dispersing the oil phase obtained in step a) into an aqueous phase to form an oil-in-water emulsion;
c) Performing a curing step to form microcapsules in the form of a slurry;
Wherein the polyfunctional monomer is added to the oil phase and/or the water phase, and
wherein a protein selected from the group consisting of potato protein, chickpea protein, pea protein, algae protein, fava bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof is added to the oil phase and/or the water phase.
According to one embodiment, the polyfunctional monomer is selected from the group consisting of at least one acid chloride, polyisocyanate, polyanhydride (e.g., polymaleic anhydride), polyepoxide, acrylate monomer, polyalkoxysilane, and mixtures thereof.
According to a particular embodiment, the polyfunctional monomer is a polyisocyanate having at least two isocyanate functional groups.
Suitable polyisocyanates for use in accordance with the present invention include aromatic polyisocyanates, aliphatic polyisocyanates, and mixtures thereof. The polyisocyanate contains at least 2, preferably at least 3, but may contain up to 6, or even only 4 isocyanate functional groups. According to a particular embodiment, triisocyanates (3 isocyanate functions) are used.
According to one embodiment, the polyisocyanate is an aromatic polyisocyanate.
The term "aromatic polyisocyanate" is meant herein to encompass any polyisocyanate comprising an aromatic moiety. Preferably, it comprises a phenyl, toluyl, xylyl, naphthyl or diphenyl moiety. More preferably a toluoyl or xylyl moiety. Preferred aromatic polyisocyanates are biuret, polyisocyanurate and trimethylolpropane adducts of diisocyanates, more preferably comprising one of the above-specified aromatic moieties. More preferably, the aromatic polyisocyanate is a polyisocyanurate of toluene diisocyanate (available under the trade name from BayerRC commercially available), trimethylolpropane adducts of toluene diisocyanate (available under the trade name +.>L75), trimethylolpropane adduct of xylylene diisocyanate (available under the trade name +.>D-110N). In a most preferred embodiment, the aromatic polyisocyanate is a trimethylolpropane adduct of xylylene diisocyanate.
According to another embodiment, the polyisocyanate is an aliphatic polyisocyanate. The term "aliphatic polyisocyanate" is defined as a polyisocyanate that does not contain any aromatic moieties. The preferred aliphatic polyisocyanate is trimerization of hexamethylene diisocyanate The trimer of isophorone diisocyanate, the trimethylolpropane adduct of hexamethylene diisocyanate (available from Mitsui Chemicals) or the biuret of hexamethylene diisocyanate (available from Bayer under the trade nameN100), more preferably biuret of hexamethylene diisocyanate.
According to another embodiment, the at least one polyisocyanate is in the form of a mixture of at least one aliphatic polyisocyanate and at least one aromatic polyisocyanate, both comprising at least two or three isocyanate functional groups, such as a mixture of biuret of hexamethylene diisocyanate and trimethylolpropane adduct of xylylene diisocyanate, a mixture of biuret of hexamethylene diisocyanate and polyisocyanurate of toluene diisocyanate, and a mixture of biuret of hexamethylene diisocyanate and trimethylolpropane adduct of toluene diisocyanate. Most preferably, it is a mixture of biuret of hexamethylene diisocyanate and trimethylolpropane adduct of xylylene diisocyanate. Preferably, when used as a mixture, the molar ratio between aliphatic polyisocyanate and aromatic polyisocyanate is from 80:20 to 10:90.
According to another embodiment, the polyfunctional monomer is an acid chloride.
According to a particular embodiment, the method comprises the steps of:
a) Preparing an oil phase comprising an acid chloride and a hydrophobic material, preferably a perfume, to form an oil phase;
b) Dispersing the oil phase obtained in step a) into an aqueous phase to form an oil-in-water emulsion;
c) Performing a curing step to form microcapsules in the form of a slurry;
wherein at least one amino compound is added to the aqueous phase before the formation of the oil-in-water emulsion and/or to the oil-in-water emulsion obtained after step b), and
wherein a protein selected from the group consisting of potato protein, chickpea protein, pea protein, algae protein, fava bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof is added to the oil phase and/or the water phase.
The embodiments described above for microcapsules according to the invention also apply to the method according to the invention. This applies in particular to hydrophobic materials, proteins, acid chlorides and amino compounds.
Proteins
According to a specific embodiment, a protein selected from the group consisting of potato protein, chickpea protein, pea protein, algae protein, broad bean protein, barley protein, oat protein, wheat gluten protein, lupin protein and mixtures thereof is added to the oil phase and/or the water phase. According to a specific embodiment, the protein is added to the oil phase. When added to the oil phase, the protein may be pre-dispersed (or pre-dissolved) in an inert solvent or any inert perfume solvent/ingredient such as benzyl benzoate, triethyl citrate, ethyl acetate, vegetable oils (such as sunflower seed oil), hexyl salicylate, neobee (caprylic/capric triglyceride), isopropyl myristate, triglycerides, D-limonene, silicone oils, mineral oils, benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenyl ethyl acetate, triacetin, ethyl citrate, methyl and ethyl salicylates, benzyl cinnamate, and mixtures thereof, or may be mixed with an active ingredient preferably comprising a perfume oil.
The protein is preferably used in an amount of 0.1 to 10 wt.%, preferably 0.5 to 7 wt.%, based on the total weight of the oil phase or based on the total weight of the aqueous phase.
According to one embodiment, the protein defined in the present invention acts as a stabilizer.
According to one embodiment, stabilizers may also be added to the aqueous phase and/or the oil phase to form an emulsion. According to one embodiment, the stabilizer is a colloidal stabilizer.
By "stabilizer" is meant a compound that is capable of stabilizing the oil/water interface into an emulsion, typically by reducing the interfacial tension between the oil phase and the aqueous phase.
In the present invention, "stabilizer" or "emulsifier" may be used indiscriminately.
According to one embodiment, the stabilizer is a colloidal stabilizer.
The colloidal stabilizer may be a polymeric emulsifier (standard emulsion), a surfactant or solid particles (pickering emulsion).
In the present invention, "molecular emulsifier" and "polymer/high molecular emulsifier" are used indiscriminately.
By "polymeric emulsifier" is meant an emulsifier having both polar groups with affinity for water (hydrophilic) and non-polar groups with affinity for oil (lipophilic). The hydrophilic portion will dissolve in the aqueous phase and the hydrophobic portion will dissolve in the oil phase, forming a thin film around the droplets.
By "surfactant" is meant a non-polymeric material having polar and non-polar groups.
According to one embodiment, the stabilizing agent is selected from the group consisting of inorganic particles, polymeric emulsifiers such as polysaccharides, proteins, glycoproteins, and mixtures thereof.
When the stabilizer is a solid particle, it may be selected from the group consisting of calcium phosphate, silica, silicate, titanium dioxide, alumina, zinc oxide, iron oxide, mica, kaolin, montmorillonite, hectorite (laponite), bentonite, perlite, dolomite, diatomaceous earth (diatomite), vermiculite, hectorite, gibbsite, illite, kaolinite, aluminosilicate, gypsum, bauxite, magnesite, talc, magnesium carbonate, calcium carbonate, diatomaceous earth (diatomaceous earth), and mixtures thereof.
According to a particular embodiment, the stabilizer is a biopolymer.
According to a particular embodiment, the stabilizer is a polymer as defined above.
By "biopolymer" is meant a biological macromolecule produced by a living organism. Biopolymers are characterized by molecular weight distributions ranging from 1,000 (1 kilo) to 1,000,000,000 (10 hundred million) daltons. These macromolecules may be carbohydrates (glycosyl groups) or proteins (amino acid groups) or a combination of both (gum base (gum)), and may be linear or branched.
According to one embodiment, the colloidal stabilizer is selected from the group consisting of: acacia, modified starch, polyvinyl alcohol, polyvinylpyrrolidone (PVP), acrylamide copolymers, inorganic particles, proteins such as soy protein, rice protein, whey protein, egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudocollagen, silk protein, sericin powder, and mixtures thereof.
When added to the oil phase, the stabilizer may be pre-dispersed (or pre-dissolved) in an inert solvent or any inert fragrance solvent/ingredient such as benzyl benzoate, triethyl citrate, ethyl acetate, vegetable oils (such as sunflower seed oil), hexyl salicylate, neobee (caprylic/capric triglyceride), isopropyl myristate, triglycerides, D-limonene, silicone oils, mineral oils, benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenyl ethyl acetate, triacetin, ethyl citrate, methyl and ethyl salicylates, benzyl cinnamate, and mixtures thereof, or may be mixed with an active ingredient preferably comprising a fragrance oil.
The stabilizer and the acid chloride may be pre-mixed and may be heated at a temperature of, for example, 10 ℃ to 80 ℃ prior to mixing with the hydrophobic material preferably comprising the perfume oil.
When the colloidal stabilizer is added to the aqueous phase, it is preferably selected from the group consisting of: acacia, modified starch, polyvinyl alcohol, polyvinylpyrrolidone (PVP), acrylamide copolymers, inorganic particles, proteins such as soy protein, rice protein, whey protein, egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudocollagen, silk protein, sericin powder, and mixtures thereof.
According to any of the above embodiments of the invention, the dispersion comprises about 0.01% to 3.0% of at least one stabilizer, preferably a colloidal stabilizer, the percentages being expressed on a w/w basis relative to the total weight of the oil-in-water emulsion obtained after step b). In yet another aspect of the invention, the dispersion comprises from about 0.05% to 2.0%, preferably from 0.05 to 1%, of at least one stabilizer, preferably a colloidal stabilizer. In a further form of the invention, the dispersion comprises from about 0.1% to 1.6%, preferably from 0.1% to 0.8% by weight of at least one stabilizer, preferably a colloidal stabilizer.
Acyl chlorides
The acid chloride used in the process may be defined as described previously for the microcapsules.
The weight ratio between the acid chloride and the hydrophobic material is preferably 0.01 to 0.09, more preferably 0.02 to 0.07.
According to a particular embodiment, the acid chloride is used in an amount of 1.7 to 7 wt%, preferably 2.5 to 5 wt%, based on the total weight of the hydrophobic material.
The acid chloride may be dissolved (or dispersed) directly in the perfume oil, or may be pre-dispersed (or pre-dissolved) in an inert solvent or any inert perfume solvent/ingredient such as benzyl benzoate, triethyl citrate, ethyl acetate, vegetable oils (e.g. sunflower seed oil), hexyl salicylate, neobee (caprylic/capric triglyceride), isopropyl myristate, triglycerides, D-limonene, silicone oils, mineral oils, benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenyl ethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylates, benzyl cinnamate and mixtures thereof, and then mixed with the perfume oil.
Alkali
According to one embodiment, the aqueous phase comprises a base (base) preferably selected from the group consisting of sodium carbonate, sodium bicarbonate, sodium hydroxide, guanidine carbonate, triethanolamine and mixtures thereof.
According to a particular embodiment, the base is not an amino compound.
According to one embodiment, the aqueous phase comprises a base preferably selected from the group consisting of sodium carbonate, sodium bicarbonate, sodium hydroxide and mixtures thereof.
The amount of base added may be from 0.01 to 1.5 wt%, preferably from 0.01 to 0.7 wt%, based on the total weight of the aqueous phase.
Amino compounds
According to one embodiment, at least one amino compound (amino compound a) is added to the aqueous phase before forming the oil-in-water emulsion and/or to the oil-in-water emulsion obtained after step b).
According to one embodiment, at least the functional group NH of the amino compound 2 The molar ratio with the functional group COCl of the acid chloride is 0.2 to 3, preferably 0.5 to 2, more preferably 0.2 to 1.
According to one embodiment, at least one further amino compound (amino compound B) is added to the aqueous phase before the formation of the oil-in-water emulsion and/or to the oil-in-water emulsion obtained after step B).
According to one embodiment, at least one further amino compound (amino compound C) other than amino compounds a and B is added to the aqueous phase before the formation of the oil-in-water emulsion and/or to the oil-in-water emulsion obtained after step B).
According to one embodiment, the amino compound (a and/or B and/or C) is selected from the group consisting of: m-xylylenediamine, 1, 2-diaminocyclohexane, 1, 4-diaminocyclohexane, L-lysine ethyl ester and polyetheramineEthylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris- (2-aminoethyl) amine, 3-aminopropyl triethoxysilane, L-arginine, 1, 4-diaminobutane, 2-dimethyl-1, 3-propanediamine, 1, 3-diaminopentane (Dytek EP diamine), 1, 2-diaminopropane, triethylenetetramine, amines having disulfide bonds such as cystamine, cystamine hydrochloride, cystine, cystamine hydrochlorideAmino acids, cystine dialkyl esters, cystine dialkyl ester hydrochlorides, and mixtures thereof.
According to one embodiment, the amino compound (a and/or B and/or C) is selected from the group consisting of: cystamine, cystamine hydrochloride, cystine hydrochloride, cystine dialkyl ester hydrochloride, m-xylylene diamine, 1, 2-diaminocyclohexane, 1, 4-diaminocyclohexane, polyetheramine, ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris- (2-aminoethyl) amine, 3-aminopropyl triethoxysilane, 1, 4-diaminobutane, 2-dimethyl-1, 3-propylenediamine, 1, 3-diaminopentane (Dytek EP diamine), 1, 2-diaminopropane, triethylenetetramine, 1, 3-diaminopropane; urea; ethylene urea; aminoguanidine bicarbonate; 1- (2-aminoethyl) imidazolin-2-one; n- (3-aminopropyl) -N-dodecylpropane-1, 3-diamine; n1- (2-aminoethyl) -N1-dodecyl-1, 2-ethylenediamine; aminoethylethanolamine; n1- (3-aminopropyl) propane-1, 3-diamine, polyethylenimine, amino acids such as L-lysine, L-arginine, L-histidine, L-tryptophan, L-serine, L-glutamine, L-threonine, L-leucine, and/or oligomers and polymers derived therefrom, and mixtures thereof.
According to one embodiment, at least one amino compound (amino compound a) is added to the aqueous phase before forming the oil-in-water emulsion and/or to the oil-in-water emulsion obtained after step b).
According to one embodiment, at least one amino compound (amino compound a), preferably an amino acid, more preferably L-lysine, is added to the aqueous phase before the formation of the oil-in-water emulsion, and at least one amino compound (amino compound B) or at least two amino compounds (amino compound B and amino compound C) are added to the aqueous phase before the formation of the oil-in-water emulsion and/or to the oil-in-water emulsion obtained after step B), wherein amino compound B is preferably ethylenediamine, and wherein amino compound C is preferably diethylenetriamine.
The base may also be added to the aqueous phase and/or to the oil-in-water emulsion.
According to one embodiment, functional groups NH of ethylenediamine and diethylenetriamine (EDA+DETA) 2 The molar ratio with respect to the functional group COCl of the acid chloride is from 0.2 to 3, preferably from 0.5 to 2, more preferably from 0.2 to 1.
According to a particular embodiment, a multivalent salt (e.g. calcium chloride, magnesium chloride, zinc chloride, ferric chloride) is added after step b), before or during step c).
Carbohydrates
According to one embodiment, the carbohydrate is added to the aqueous phase and/or to the oil phase.
According to one embodiment, by "carbohydrate" is understood a polymer or oligomer having a number of units greater than 2.
According to another embodiment, the carbohydrate, amino compound a and amino compound B are different components.
According to one embodiment, at least one carbohydrate is added to the oil phase and/or to the aqueous phase.
According to one embodiment, the carbohydrate is not a polyphenol.
According to one embodiment, the carbohydrate is not a functionalized carbohydrate.
According to one embodiment, the carbohydrate is a polysaccharide.
According to one embodiment, the polysaccharide is an anionic polysaccharide.
According to a particular embodiment, the polysaccharide is added to the aqueous phase.
The polysaccharide is preferably selected from the group consisting of anionic salts of alginic acid, preferably sodium alginate, pectin, lignin, anionically modified starch, carboxymethyl cellulose, and mixtures thereof.
According to a particular embodiment, the carbohydrate is an anionic salt of alginic acid, preferably sodium alginate.
"sodium alginate salt" and "sodium alginate" may be used indifferently.
According to a particular embodiment, the carbohydrate is used in an amount of 0.1 to 5% by weight, preferably 0.5 to 1.1% by weight, based on the total weight of the aqueous phase.
Multiple microcapsule system
According to one embodiment, the microcapsules of the invention (microcapsules of the first type) may be used in combination with microcapsules of the second type.
Another object of the invention is a microcapsule delivery system comprising:
microcapsules of the invention as microcapsules of the first type, and
-microcapsules of a second type, wherein the microcapsules of the first type are different from the microcapsules of the second type in their hydrophobic material and/or their wall material and/or their coating layer material.
According to a particular embodiment, the microcapsule delivery system is in the form of a slurry.
The walls of the second type of microcapsules may vary. As non-limiting examples, the polymeric shell of the second type of microcapsules comprises a material selected from the group consisting of polyureas, polyurethanes, polyamides, polyhydroxyalkanoates, polyacrylates, polyesters, polyamino esters, polyepoxides, polysiloxanes, polycarbonates, polysulfonamides, urea-formaldehyde resins, melamine formaldehyde resins crosslinked with polyisocyanates or aromatic polyols, melamine urea resins, melamine glyoxal resins, gelatin/acacia shell walls, and mixtures thereof.
The second type of microcapsules may comprise an oil-based core comprising a hydrophobic active, preferably a perfume, and a composite shell comprising a first material and a second material, wherein the first material is different from the second material, the first material is a coacervate, and the second material is a polymeric material. In a particular embodiment, the weight ratio between the first material and the second material is 50:50 to 99.9:0.1. In a particular embodiment, the coacervate comprises a first polyelectrolyte, preferably selected from the group consisting of proteins (e.g. gelatin), polypeptides or polysaccharides (e.g. chitosan), most preferably gelatin, and a second polyelectrolyte, preferably alginate, cellulose derivatives, guar gum, pectate, carrageenan, polyacrylic acid and methacrylic acid or xanthan gum, or a vegetable gum such as acacia gum (gum arabic), most preferably gum arabic. The coacervate first material may be chemically hardened using a suitable cross-linking agent, such as glutaraldehyde, glyoxal, formaldehyde, tannic acid, or genipin, or may be enzymatically hardened using an enzyme, such as transglutaminase. The second polymeric material may be selected from the group consisting of polyureas, polyurethanes, polyamides, polyesters, polyacrylates, polysiloxanes, polycarbonates, polysulfonamides, urea and formaldehyde polymers, melamine and urea polymers, or melamine and glyoxal polymers, and mixtures thereof, preferably polyureas and/or polyurethanes. The second material is preferably present in an amount of less than 3 wt%, preferably less than 1 wt%, based on the total weight of the microcapsule slurry of the second type.
As non-limiting examples, the shells of the second type of microcapsules may be aminoplast-based, polyurea-based or polyurethane-based. The shell of the second type of microcapsules may also be composite, i.e. organic-inorganic, e.g. a composite shell consisting of at least two types of crosslinked inorganic particles, or a shell resulting from hydrolysis and condensation reactions of polyalkoxysilane macromer compositions.
According to one form, the shell of the second type of microcapsules comprises an aminoplast copolymer, such as melamine-formaldehyde or urea-formaldehyde or cross-linked melamine formaldehyde or melamine glyoxal.
According to another form, the shell of the second type of microcapsules is polyurea-based, made from, for example, but not limited to, isocyanate-based monomers and amine-containing cross-linking agents such as guanidine carbonate and/or guanazole. Some polyurea microcapsules comprise a polyurea wall that is the polymerization reaction product between at least one polyisocyanate comprising at least two isocyanate functional groups and at least one reactant selected from amines (e.g., water-soluble guanidine salts and guanidine); colloidal stabilizers or emulsifiers; and encapsulated fragrances. However, the use of amines may be omitted. According to a particular form, the colloidal stabilizer comprises an aqueous solution of 0.1% to 0.4% of a cationic copolymer of polyvinyl alcohol, 0.6% to 1% of vinylpyrrolidone and quaternized vinylimidazole (all percentages being defined with respect to the total weight of the colloidal stabilizer). According to another form, the emulsifier is an anionic or amphiphilic biopolymer, which may be selected, for example, from the group consisting of acacia, soy protein, gelatin, sodium caseinate and mixtures thereof.
According to another embodiment, the microcapsule wall material of the second type of microcapsules may comprise any suitable resin, including in particular melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, etc. Suitable resins include the reaction products of aldehydes with amines, and suitable aldehydes include formaldehyde and glyoxal. Suitable amines include melamine, urea, benzoguanamine, glycoluril and mixtures thereof. Suitable melamines include methylolmelamine, methylated methylolmelamine, iminomelamine, and mixtures thereof. Suitable ureas include dimethylol urea, methylated dimethylol urea, urea-resorcinol, and mixtures thereof. Suitable materials for fabrication may be obtained from one or more of the following companies: solutia Inc. (St Louis, missouri U.S. A.), cytec Industries (West Paterson, new Jersey U.S. A.), sigma-Aldrich (St. Louis, missouri U.S. A.).
According to another embodiment, the second type of microcapsules is single shell aminoplast core-shell microcapsules, obtainable by a process comprising the steps of:
1) Mixing a perfume oil with at least one polyisocyanate having at least two isocyanate functional groups to form an oil phase;
2) Dispersing or dissolving an aminoplast resin and optionally a stabilizer in water to form an aqueous phase;
3) Preparing an oil-in-water dispersion by mixing an oil phase and an aqueous phase, wherein the average droplet size is from 1 to 100 microns;
4) Performing a curing step to form walls of the microcapsules; and
5) Optionally, the final dispersion is dried to obtain dried core-shell microcapsules.
According to one embodiment, the second type of microcapsules is formaldehyde free capsules. A typical process for preparing an aminoplast formaldehyde-free microcapsule slurry comprises the steps of:
1) An oligomeric composition is prepared comprising the reaction product of, or obtained by reacting together:
a. in melamine form or melamine with at least one catalyst comprising two NH groups 2 C of functional groups 1 -C 4 A polyamine component in the form of a mixture of compounds;
b. glyoxal, C 4-6 Aldehyde component in the form of a mixture of 2, 2-dialkoxyacetaldehyde and optionally glyoxylate, glyoxal/C of said mixture 4-6 The molar ratio of the 2, 2-dialkoxyl ethanol is 1/1 to 10/1; and
c. a proton acid catalyst;
2) Preparing an oil-in-water dispersion, wherein the droplet size is from 1 to 600 microns, and comprising:
a. An oil;
b. aqueous medium
c. At least one oligomeric composition as obtained in step 1;
d. at least one cross-linking agent selected from the group consisting of:
i.C 4 -C 12 aromatic or aliphatic di-or triisocyanates and their biurets, triureas, trimers, trimethylolpropane adducts and mixtures thereof; and/or
Di-or tri-oxirane compounds of the formula
A- (ethylene oxide-2-ylmethyl) n
Wherein n represents 2 or 3, A represents C optionally containing 2 to 6 nitrogen and/or oxygen atoms 2 -C 6 A group;
e. optionally, comprise two NH 2 C of functional groups 1 -C 4 A compound;
3) Heating the dispersion;
4) The dispersion was cooled.
In another particular embodiment, the second type of microcapsules comprises:
an oil-based core comprising a hydrophobic active, preferably a perfume,
-optionally an inner shell made of polymerized multifunctional monomer;
-a biopolymer shell comprising proteins, wherein at least one protein is cross-linked.
According to a specific embodiment, the protein is selected from the group consisting of milk proteins, caseinates such as sodium or calcium caseinate, casein, whey proteins, hydrolysed proteins, gelatine, gluten, pea proteins, soy proteins, silk proteins and mixtures thereof, preferably sodium caseinate, most preferably sodium caseinate.
According to a specific embodiment, the protein comprises sodium caseinate and globular proteins, preferably selected from the group consisting of whey proteins, beta-lactoglobulin, ovalbumin, bovine serum albumin, vegetable proteins and mixtures thereof.
The protein is preferably a mixture of sodium caseinate and whey protein.
According to a specific embodiment, the biopolymer shell comprises a cross-linked protein selected from the group consisting of sodium caseinate and/or whey protein.
According to a particular embodiment, the second type of microcapsule slurry comprises at least one microcapsule made of:
-an oil-based core comprising a hydrophobic active, preferably a perfume;
-an inner shell made of polymerized polyfunctional monomers; polyisocyanates having at least two isocyanate functions are preferred;
-a biopolymer shell comprising proteins, wherein at least one protein is cross-linked; wherein the protein preferably comprises a mixture comprising sodium caseinate and globular protein, preferably whey protein;
-optionally, at least one external mineral layer.
According to one embodiment, the sodium caseinate and/or whey protein is a cross-linked protein.
The weight ratio between sodium caseinate and whey protein is preferably 0.01 to 100, preferably 0.1 to 10, more preferably 0.2 to 5.
In another particular embodiment, the second type of microcapsules are polyamide core-shell polyamide microcapsules comprising:
-an oil-based core comprising a hydrophobic active, preferably a perfume, and
-a polyamide shell comprising or obtainable from:
the acid chloride is used as a base for the acid,
a first amino compound, and
a second amino compound.
According to a particular embodiment, the microcapsules of the second type comprise:
-an oil-based core comprising a hydrophobic active, preferably a perfume, and
-a polyamide shell comprising or obtainable from:
acid chloride, preferably in an amount of 5 to 98%, preferably 20 to 98%, more preferably 30 to 85% w/w;
a first amino compound, preferably in an amount of 1% to 50% w/w, preferably 7 to 40% w/w;
a second amino compound, preferably in an amount of 1% to 50% w/w, preferably 2 to 25% w/w;
stabilizers, preferably biopolymers, preferably in an amount of 0 to 90%, preferably 0.1 to 75%, more preferably 1 to 70%.
According to a particular embodiment, the microcapsules of the second type comprise:
-an oil-based core comprising a hydrophobic active, preferably a perfume, and
-a polyamide shell comprising or obtainable from:
the acid chloride is used as a base for the acid,
a first amino compound which is an amino acid, preferably selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan and/or mixtures thereof,
a second amino compound selected from the group consisting of ethylenediamine, diethylenetriamine, cystamine and/or mixtures thereof, and
a biopolymer selected from the group consisting of casein, sodium caseinate, bovine serum albumin, whey protein and/or mixtures thereof.
According to another form, the shell of the microcapsules of the second type is polyurea-or polyurethane-based. Examples of methods for preparing polyurea-and polyurethane-based microcapsule slurries are described, for example, in International patent application publication No. WO2007/004166, european patent application publication No. EP 2300146 and European patent application publication No. EP 25799. Generally, the process for preparing a polyurea-or polyurethane-based microcapsule slurry comprises the steps of:
a) Dissolving at least one polyisocyanate having at least two isocyanate groups in an oil to form an oil phase;
b) Preparing an aqueous solution of an emulsifier or colloidal stabilizer to form an aqueous phase;
c) Adding the oil phase to the aqueous phase to form an oil-in-water dispersion, wherein the average droplet size is from 1 to 500 μm, preferably from 5 to 50 μm; and
d) Conditions sufficient to initiate interfacial polymerization are applied and microcapsules in the form of a slurry are formed.
Perfuming composition and consumer product
The microcapsules of the present invention may be used in combination with an active ingredient. Accordingly, one object of the present invention is a composition comprising:
(i) Microcapsules or microcapsule slurries as defined above;
(ii) The active ingredient is preferably selected from the group consisting of: cosmetic ingredients, skin care ingredients, fragrance ingredients, flavor ingredients, malodor counteracting ingredients, germicide ingredients, fungicide ingredients, pharmaceutical or agrochemical ingredients, sanitizing ingredients, insect repellents or attractants, and mixtures thereof.
The capsules of the present invention exhibit good performance in terms of stability in challenging media.
Another object of the present invention is a perfuming composition comprising:
(i) A microcapsule or microcapsule slurry as defined above, wherein the oil comprises a perfume;
(ii) At least one ingredient selected from the group consisting of a fragrance carrier, a fragrance co-ingredient, and mixtures thereof;
(iii) Optionally, at least one fragrance adjuvant.
As liquid perfume carriers, emulsifying systems, i.e. solvents and surfactant systems, or solvents commonly used in perfumery, can be cited as non-limiting examples. A detailed description of the nature and type of solvents commonly used in perfumery is not exhaustive. However, as non-limiting examples, solvents such as dipropylene glycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2- (2-ethoxyethoxy) -1-ethanol or ethyl citrate, which are most commonly used, may be cited. For compositions comprising both a perfume carrier and perfume co-ingredients, other suitable perfume carriers may be ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins, other than those previously identified, e.g. under the trademark(origin: exxon Chemical) known, or glycol ethers and glycol ether esters, e.g. under the trademark(sources: dow Chemical Company) are known. By "perfume co-ingredient" is meant herein a compound which is used in a perfuming formulation or composition to impart a hedonic effect, and which is not a microcapsule as defined above. In other words, to be considered as a perfuming co-ingredient, it must be recognized by a person skilled in the art as being able to impart or modify in an active or pleasant way the odor of a composition, not just as having an odor.
The nature and type of the perfuming co-ingredients present in the perfuming composition do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them according to his general knowledge and to the intended use or application and the desired organoleptic effect. In general, these perfuming co-ingredients belong to different chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenes, nitrogen-or sulfur-containing heterocyclic compounds and essential oils, and the perfuming co-ingredients can be of natural or synthetic origin. In any event, many of these co-ingredients are listed in references such as the s.arctander works Perfume and Flavor Chemicals,1969,Montclair,New Jersey,USA or newer versions thereof or other works of similar nature, as well as the patent literature that is abundant in the fragrance arts. It will also be appreciated that the co-ingredients may also be compounds known to release various types of perfuming compounds in a controlled manner. The co-ingredient may be selected from the group consisting of: 4- (dodecylthio) -4- (2, 6-trimethyl-2-cyclohexen-1-yl) -2-butanone, 4- (dodecylthio) -4- (2, 6-trimethyl-1-cyclohexen-1-yl) -2-butanone, trans-3- (dodecylthio) -1- (2, 6-trimethyl-3-cyclohexen-1-yl) -1-butanone, 2- (dodecylthio) oct-4-one, 2-phenylethyl oxy (phenyl) acetate, 3, 7-dimethyloct-2, 6-dien-1-yl oxy (phenyl) acetate, 3-hex-1-yl oxy (Z) -hex-en-1-yl, 3, 7-dimethyl-2, 6-octadien-1-yl oxy (2- ((2-methylundec-1-en-1-yl) oxy) benzene, 1-methyl-4-ethoxy-benzyl-1- (3-butyl) benzene-3-ethoxy-4-methyl-4-but-benzyl-3-ethoxy-phenyl) acetate, 1- (((Z) -hex-3-en-1-yl) oxy) -2-methylundec-1-ene, (2- ((2-methylundec-1-en-1-yl) oxy) ethoxy) benzene, 2-methyl-1- (oct-3-yloxy) undec-1-ene, 1-methoxy-4- (1-phenethoxyprop-1-en-2-yl) benzene, 1-methyl-4- (1-phenethoxyprop-1-en-2-yl) benzene, 2- (1-phenethoxyprop-1-en-2-yl) naphthalene, (2-phenethoxyvinyl) benzene, 2- (1- ((3, 7-dimethyloct-6-en-1-yl) oxy) prop-1-en-2-yl) naphthalene, (2- ((2-pentylidene) methoxy) ethyl) benzene, 4-allyl-2-methoxy-1- ((2-methoxy-2-phenylvinyl) oxy) benzene, (2- ((2-heptylethylene) cyclopentyl) benzene, 1-isopropyl-4-methyl-2- ((2-pentylidene) methoxy) benzene, 2-methoxy-1- ((2-pentylidene) methoxy) -4-propylbenzene, 3-methoxy-4- ((2-methoxy-2-phenylvinyl) oxy) benzaldehyde, 4- ((2- (hexyloxy) -2-phenylvinyl) oxy) -3-methoxybenzaldehyde or a mixture thereof.
By "perfume adjuvant" is meant herein an ingredient capable of imparting additional benefits (e.g., color, specific lightfastness, chemical stability, etc.). A detailed description of the nature and type of adjuvants commonly used in perfuming bases is not exhaustive, but it must be mentioned that the ingredients are well known to a person skilled in the art.
Preferably, the perfuming composition according to the invention comprises from 0.01 to 30% by weight of microcapsules as defined above.
The microcapsules of the present invention can be advantageously used in many fields of application and in consumer products. The microcapsules may be used in liquid form suitable for use in liquid consumer products, or in powder form suitable for use in powder consumer products.
According to a particular embodiment, the consumer product as defined above is a liquid and comprises:
a) 2 to 65 wt% of at least one surfactant, relative to the total weight of the consumer product;
b) Water or a hydrophilic organic solvent miscible with water; and
c) A microcapsule slurry or microcapsules as defined above,
d) Optionally, a non-encapsulated perfume.
According to a particular embodiment, the consumer product as defined above is in powder form and comprises:
a) 2 to 65 wt% of at least one surfactant, relative to the total weight of the consumer product;
b) Microcapsule powder as defined above.
c) Alternatively, a perfume powder, which is different from the microcapsules as defined above.
In the case of microcapsules comprising a perfume oil-based core, the products of the invention are particularly useful in perfumed consumer products, such as products belonging to the class of high quality fragrances or "functional" perfumes. Functional perfumes include, inter alia, personal care products including hair care, body cleaning, skin care, hygiene care, and household care products including laundry care, surface care, and air care. Another object of the present invention is therefore a perfumed consumer product comprising as perfuming ingredient a microcapsule as defined above or a perfuming composition as defined above. The perfume ingredients of the consumer product may be a combination of perfume microcapsules as defined above and free or non-encapsulated perfume, as well as other types of perfume microcapsules other than those disclosed herein.
In particular, the following liquid consumer products are another object of the present invention, comprising:
a) 2 to 65 wt% of at least one surfactant, relative to the total weight of the consumer product;
b) Water or a hydrophilic organic solvent miscible with water; and
c) A perfuming composition as defined above.
Also, the following powdered consumer products are part of the present invention, comprising:
(a) 2 to 65 wt% of at least one surfactant, relative to the total weight of the consumer product; and
(b) A perfuming composition as defined above.
Thus, the microcapsules of the present invention may be added as such or as part of the perfuming composition of the present invention to a perfumed consumer product.
For the sake of clarity, it has to be mentioned that "perfumed consumer product" refers to a consumer product intended to deliver perfuming effects of different benefits to the surface to which it is applied (for example skin, hair, fabric, paper or household surfaces) or in the air (air fresheners, body fragrances/deodorants, etc.). In other words, a perfumed consumer product according to the invention is a processed product comprising a functional formulation (also referred to as a "base") and a benefit agent, wherein an effective amount of microcapsules according to the invention.
The nature and type of the other ingredients of the perfumed consumer product do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them according to his general knowledge and to the nature and desired effect of said product. Base formulations for consumer products in which microcapsules of the present invention may be incorporated can be found in a large number of documents relating to such products. These formulations do not guarantee the detailed description herein, which is not exhaustive in any way. The person skilled in the art of formulating such consumer products is fully enabled to select the appropriate components according to his general knowledge and available literature.
Non-limiting examples of suitable perfumed consumer products may be perfumes such as high quality perfumes, colognes, after-shave, body perfume; fabric care products, such as liquid or solid detergents, tablets and sachets (single or multi-chambered), fabric softeners, dry laundry, fabric fresheners, ironing waters, or bleaches; personal care products, such as hair care products (e.g. shampoos, hair conditioners, coloring agents or hair sprays), cosmetic preparations (e.g. vanishing creams, body lotions, or body fragrances (deodorants) or antiperspirants), or skin care products (e.g. soaps, bath or shower mousses, body washes, bath oils or gels, bath salts, or hygiene products); air care products, such as air fresheners or "ready to use" powdered air fresheners; or household care products, such as general-purpose cleaners, liquid or powdered or tablet dishwashing products, toilet cleaners or products for cleaning various surfaces, such as sprays and wipes for treating/refreshing textiles or hard surfaces (floors, tiles, stone floors, etc.); sanitary products such as sanitary napkins, diapers, and toilet paper.
Another object of the invention is a consumer product comprising:
-a personal care active base material
Microcapsules or microcapsule slurries as defined above or perfuming compositions as defined above,
wherein the consumer product is in the form of a personal care composition.
Personal care active binders into which microcapsules of the present invention can be incorporated can be found in a large number of documents relating to such products. These formulations do not guarantee the detailed description here, which is not exhaustive in any way. The person skilled in the art of formulating such consumer products is fully enabled to select the appropriate components according to his general knowledge and available literature.
The personal care composition is preferably selected from the group consisting of: hair care products (e.g. shampoos, hair conditioners, coloring preparations or hair sprays), cosmetic preparations (e.g. vanishing creams, body lotions, or body fragrances or antiperspirants), or skin care products (e.g. perfumed soaps, bath or shower mousses, shower gels, bath or oil or gels, bath salts, or hygiene products).
Another object of the invention is a consumer product comprising:
-household care or fabric care active base
Microcapsules or microcapsule slurries as defined above or perfuming compositions as defined above,
wherein the consumer product is in the form of a home care or fabric care composition.
Home care or fabric care binders into which the microcapsules of the present invention can be incorporated can be found in a large number of documents relating to such products. These formulations do not guarantee the detailed description here, which is not exhaustive in any way. The person skilled in the art of formulating such consumer products is fully enabled to select the appropriate components according to his general knowledge and available literature.
Preferably, the consumer product comprises from 0.1 to 15 wt%, more preferably from 0.2 to 5 wt% of microcapsules of the invention, these percentages being defined by weight relative to the total weight of the consumer product. Of course, the concentrations described above may be adjusted according to the desired benefits of each product.
An object of the present invention is a consumer product, preferably a home care or fabric care consumer product, comprising microcapsules or a microcapsule slurry as defined above, wherein the pH of the consumer product is less than 7.
An object of the present invention is a consumer product, preferably a home care or fabric care consumer product, comprising microcapsules or a slurry of microcapsules as defined above, wherein the pH of the consumer product is equal to or greater than 7.
For liquid consumer products mentioned below, an "active base" is understood to mean that the active base comprises an active material (typically comprising a surfactant) and water.
For solid consumer products mentioned hereinafter, a "active base" is understood to mean that the active base comprises active materials (generally including surfactants) and auxiliaries (e.g. bleaching agents, buffers, builders, soil release agents or soil suspending polymers (soil suspension polymers), particulate enzyme particles, corrosion inhibitors, defoamers, suds suppressors, dyes, fillers and mixtures thereof).
Fabric softener
One object of the present invention is a consumer product in the form of a fabric softener composition comprising:
-a fabric softener active base; preferably comprising at least one active material selected from the group consisting of: dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts (esterquat), hamburg ester quaternary ammonium salts (HEQ), TEAQ (triethanolamine quaternary ammonium salts), silicones, and mixtures thereof, the reactive base preferably being used in an amount of 85 to 99.95 weight percent based on the total weight of the composition,
the microcapsule slurry or microcapsules as defined above, preferably in an amount of from 0.05 to 15 wt%, more preferably from 0.1 to 5 wt%, based on the total weight of the composition,
-optionally, free perfume oil.
Liquid detergent
One object of the present invention is a consumer product in the form of a liquid detergent composition comprising:
-a liquid detergent active binder; preferably comprising at least one active material selected from the group consisting of: anionic surfactants, such as Alkylbenzenesulfonates (ABS), secondary Alkylsulfonates (SAS), primary Alcohol Sulfates (PAS), lauryl Ether Sulfates (LES), methyl Ester Sulfonates (MES), and nonionic surfactants, such as alkylamines, alkanolamides, fatty alcohol poly (ethylene glycol) ethers, fatty Alcohol Ethoxylates (FAE), ethylene Oxide (EO) and Propylene Oxide (PO) copolymers, amine oxides, alkylpolyglucosides, alkylpolyglucosamides, reactive binders are preferably used in amounts of from 85 to 99.95% by weight, based on the total weight of the composition,
the microcapsule slurry or microcapsules as defined above, preferably in an amount of from 0.05 to 15 wt%, more preferably from 0.1 to 5 wt%, based on the total weight of the composition,
-optionally, free perfume oil.
Solid detergent
One object of the present invention is a consumer product in the form of a solid detergent composition comprising:
-a solid detergent active base; preferably comprising at least one active material selected from the group consisting of: anionic surfactants, such as Alkylbenzenesulfonates (ABS), secondary Alkyl Sulfonates (SAS), primary Alcohol Sulfates (PAS), lauryl Ether Sulfates (LES), methyl Ester Sulfonates (MES), and nonionic surfactants, such as alkylamines, alkanolamides, fatty alcohol poly (ethylene glycol) ethers, fatty Alcohol Ethoxylates (FAE), ethylene Oxide (EO) and Propylene Oxide (PO) copolymers, amine oxides, alkylpolyglucosides, alkylpolyglucosamides, the reactive base is preferably used in an amount of from 85 to 99.95 weight percent based on the total weight of the composition,
The microcapsule powder or microcapsule slurry or microcapsules as defined above, preferably in an amount of from 0.05 to 15 wt%, more preferably from 0.1 to 5 wt%,
-optionally, free perfume oil.
Shampoo/body wash
One object of the present invention is a consumer product in the form of a shampoo or body wash composition comprising:
-shampoo or body wash active base; preferably comprising at least one active material selected from the group consisting of: sodium alkyl ether sulfate, ammonium alkyl ether sulfate, alkyl amphoacetates, cocamidopropyl betaine, cocamide MEA, alkyl glucosides and amino acid based surfactants and mixtures thereof, the active base is preferably used in an amount of 85 to 99.95 wt% based on the total weight of the composition,
the microcapsule slurry or microcapsules as defined above, preferably in an amount of from 0.05 to 15 wt%, more preferably from 0.1 to 5 wt%, based on the total weight of the composition,
-optionally, free perfume oil.
Rinse-off conditioner
One object of the present invention is a consumer product in the form of a rinse-off conditioner composition comprising:
-a rinse-off conditioner active base; preferably comprising at least one active material selected from the group consisting of: cetyl trimethylammonium chloride, stearyl trimethylammonium chloride, benzalkonium chloride, behenyl trimethylammonium chloride, and mixtures thereof, the active binders are preferably used in an amount of from 85 to 99.95% by weight, based on the total weight of the composition,
The microcapsule slurry or microcapsules as defined above, preferably in an amount of from 0.05 to 15 wt%, more preferably from 0.1 to 5 wt%, based on the total weight of the composition,
-optionally, free perfume oil.
Solid flavor enhancer
One object of the present invention is a consumer product in the form of a solid flavour enhancer (agent booster) comprising:
-a solid support, preferably selected from the group consisting of: urea, sodium chloride, sodium sulphate, sodium acetate, zeolite, sodium carbonate, sodium bicarbonate, clay, talc, calcium carbonate, magnesium sulphate, gypsum, calcium sulphate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, sugars such as sucrose, monosaccharides, disaccharides and polysaccharides and derivatives such as starch, cellulose, methylcellulose, ethylcellulose, propylcellulose, polyols/sugar alcohols such as sorbitol, maltitol, xylitol, erythritol and isomalt, PEG, PVP, citric acid or any water-soluble solid acid, fatty alcohols or fatty acids and mixtures thereof,
the microcapsule slurry or microcapsules as defined above, which are in powder form, are preferably present in an amount of 0.05 to 15 wt%, more preferably 0.1 to 5 wt%, based on the total weight of the composition.
-optionally, free perfume oil.
Liquid fragrance enhancer
One object of the present invention is a consumer product in the form of a liquid flavour enhancer comprising:
the aqueous phase is chosen to be the one,
-a surfactant system consisting essentially of one or more than one nonionic surfactant, wherein the surfactant system has an average HLB of from 10 to 14, preferably selected from the group consisting of: ethoxylated aliphatic alcohols, POE/PPG (polyoxyethylene and polyoxypropylene) ethers, mono-and polyglycerol esters, sucrose ester compounds, polyoxyethylene hydroxy esters, alkyl polyglucosides, amine oxides, and combinations thereof;
-a linker selected from the group consisting of: alcohols, salts and esters of carboxylic acids, salts and esters of hydroxycarboxylic acids, fatty acid salts, glycerin fatty acids, surfactants having an HLB of less than 10, and mixtures thereof, and
a microcapsule slurry or microcapsule as defined above, in the form of a slurry, preferably in an amount of 0.05 to 15 wt%, more preferably 0.1 to 5 wt%, based on the total weight of the composition.
-optionally, free perfume oil.
Hair dye
One object of the present invention is a consumer product in the form of an oxidative hair coloring composition comprising:
-an oxidizing phase comprising an oxidizing agent and a basic phase comprising a basic agent, a dye precursor and a coupling compound; wherein the dye precursor and the coupling compound form an oxidative hair dye in the presence of an oxidizing agent, preferably in an amount of 85 to 99.95 wt%,
the microcapsules or microcapsule slurries as defined above are preferably present in an amount of from 0.05 to 15 wt%, more preferably from 0.1 to 5 wt%,
-optionally, free perfume oil.
Perfuming composition
According to a particular embodiment, the consumer product is in the form of a perfuming composition comprising, based on the total weight of the perfuming composition:
from 0.1 to 30% by weight, preferably from 0.1 to 20% by weight, of microcapsules or microcapsule slurries as defined above,
0 to 40% by weight, preferably 3 to 40% by weight, of a perfume, and
20 to 90% by weight, preferably 40 to 90% by weight, of ethanol.
The invention will now be further described by way of examples. It should be understood that the claimed invention is not intended to be limited in any way by these embodiments.
Examples
General procedure
The protein is optionally dispersed in an inert solvent (e.g., benzyl Benzoate (BB) or Neobe) and maintained under agitation at 60℃for 30 minutes. The solution and a polyfunctional monomer (e.g., benzene-1, 3, 5-tricarboxyl chloride-BTC) are added to a perfume oil (25 g or 30 g-see Table 1) at room temperature to form an oil phase. The oil phase is mixed with water (94 g), the latter comprising at least one amino compound (first amino compound) and optionally a base. The reaction mixture was stirred with an Ultra Turrax at 24,000rpm for 30 seconds or 1 minute to give an emulsion. At least one amino compound (second amino compound and optionally a third amino compound) is dissolved in water (5 g) and the solution is added dropwise to the emulsion. The reaction mixture was stirred at 60 ℃ for 4 hours to give a white dispersion.
Alternatively, the second and optionally third amino compound may be added to the aqueous phase prior to the emulsification step (see capsules F2-F5).
Table 1: perfume oil
Composition of the components | % in oil |
2-Methylpentanoic acid ethyl ester | 3.20% |
Eucalyptol | 7.80% |
2, 4-dimethyl-3-cyclohexene-1-carbaldehyde | 0.75% |
Aldehyde C 10 | 0.75% |
Citronellonitrile (citronellyl nitrile) | 4.30% |
Isobornyl acetate | 3.00% |
Acetic acid 2-tert-butyl-1-cyclohexyl ester | 9.80% |
Citronellyl acetate | 1.30% |
2-methylundecalaldehyde | 3.00% |
Diphenyl ether | 0.80% |
Aldehyde C 12 | 1.30% |
Dicyclopentadienyl acetate | 9.85% |
Beta-ionone | 3.30% |
Gamma-undecalactone | 18.75% |
Salicylic acid hexyl ester | 15.90% |
Salicylic acid benzyl ester | 16.20% |
Example 1
Preparation of Polyamide microcapsules (Potato protein as protein)
Table 2: composition of Capsule A (CA)
1) Solanic 200; the source is as follows: AVEBE of Netherlands
2) 1,3, 5-benzenetricarboxylic acid chloride; the source is as follows: aldrich Switzerland
* Adding 0.5g CaCl before the emulsification step 2
EDA: ethylenediamine-source: aldrich Switzerland
DETA: diethylenetriamine-source: aldrich Switzerland
Example 2
Preparation of Polyamide microcapsules (Using chickpea protein)
Table 3: composition of Capsule B (CB)
1) ChickP G910; the source is as follows: the color column ChickP Protein Ltd of the color column,
2) 1,3, 5-benzenetricarboxylic acid chloride; the source is as follows: aldrich Switzerland
Example 3
Preparation of Polyamide microcapsules (pea protein is used)
Table 4: composition of Capsule C (CC)
1) Nutrilys F85F; the source is as follows: roquette of france
2) 1,3, 5-benzenetricarboxylic acid chloride; the source is as follows: aldrich Switzerland
Example 4
Preparation of Polyamide microcapsules
Table 5: composition of Capsule D (CD)
1) Vitessance Pulse 3600; the source is as follows: germany Ingredion
2) Everpro; the source is as follows: evergain, america
3) 1,3, 5-benzenetricarboxylic acid chloride; the source is as follows: aldrich Switzerland
Example 5
Preparation of Polyamide microcapsules (use of pretreated Potato protein as protein)
Table 6: composition of Capsule E (CE)
Denaturation process:
a2% protein solution was prepared and NaCl was added at a concentration of 100 mmol/L. The solution was heated at 90℃for 90 minutes. Once cooled, the pH of the solution was adjusted to 9.5 with 1M NaOH. The solution is then freeze-dried (the solution may also be spray-dried).
Example 6
Preparation of Polyamide microcapsules
Table 7: composition of Capsule F (CF)
* Adding amine before the emulsification step
* Adding CaCl prior to emulsification step 2
CYS HCL: cystamine hydrochloride, source: aldrich Switzerland
Example 7
Stability manifestation
The microcapsules of the present invention were dispersed in the fabric softener compositions described in table 8 to obtain a concentration of encapsulated perfume oil of 0.116%.
Table 8: fabric conditioner composition
Product(s) | Weight percent |
Stepantex VL 90A | 8.88 |
10% of calcium chloride solution | 0.36 |
Proxel GXL | 0.04 |
Spice | 1.00 |
Water and its preparation method | 89.72 |
Totals to | 100 |
The procedure is as follows:
sample extraction:
the Internal Standard (ISTD) used for quantification is ethyl dodecanoate. A total of three samples of 2g were weighed into a 20mL flask and extracted with 10mL of a 9/1 isooctane/diethyl ether solution containing 5mg/L ISTD. The sample was then shaken using Turbulat (1 hour; speed = 52 rpm) and then allowed to stand for 15-30 minutes until decanted completely. The top of the organic layer was sampled using a 2mL syringe and filtered through a 0.20 μm PTFE filter in a GC vial. Sample extraction was performed in triplicate.
Analysis conditions:
gas chromatography was performed using a 7890B Agilent instrument coupled to a 5977B MS detector. The instrument was equipped with a pneumatic control module to ensure a back flushing system and two 15m x 250 μm x 0.25 μm DB-1MS chromatographic columns. Helium was used as the carrier gas at an inlet temperature and pressure of 250 c and 10.3psi. The split mode was configured with a split ratio of 20:1 and a split flow of 20mL/min, and the gas economizer was activated at a flow rate of 15mL/min after 2 minutes. The oven program is kept at 50 ℃ for 5 minutes, the temperature is increased to 230 ℃ at 15 ℃/minute, the temperature is kept at 230 ℃ for 1 minute, and the back blowing is realized after 4 minutes of operation; the column flow rate to the MSD was then 3.45mL/min, the flow rate to the inlet was-3.05 mL/min, and the auxiliary pressure was 30psi. The MS temperatures of the quadrupole and ion source were 150℃and 230℃respectively, the scan range was 25 to 450m/z, and the solvent delay was 4 minutes.
And (3) calibrating:
quantifying the sample with a standard curve; calibration and validation spots were prepared in a 9/1 isooctane/diethyl ether solution containing 5mg/L ISTD (first method).
The second calibration was prepared in a softener base and extracted according to the same protocol as the samples to compare and check the results obtained in the first method.
Table 9: stability (perfume leakage at 37 ℃ C. -3 days/1 month)
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* Not measured
It can be concluded that the microcapsules of the present invention show good stability in challenging binders.
Example 8
Biodegradability of microcapsules according to the invention
Extraction of the Shell(following the method disclosed in Gasparini and all in Molecules 2020,25,718)
The aqueous phase of the microcapsule slurry was removed by vacuum filtration with a Gooch filter crucible (porosity 4) and the powder was dried. The recovered solids were ground for 30 seconds using a breaker IKA tube mill control. The resulting paste (fragrance oil + polymer shell) was suspended in 300mL of ethyl acetate and the mixture was stirred at room temperature for 1 hour. The solids were collected by vacuum filtration with a gulf filter crucible (porosity 4). This extraction step was repeated 5 times to remove the maximum amount of fragrance oil from the shell. The powder was dried under vacuum (10 mBar) at 50 ℃ until the weight of polymer monitored by gravimetric analysis was constant. The resulting powder was milled using a breaker IKA tube mill control for 1 minute 30 seconds, suspended in deionized water (0.5% w/w) and stirred at 300RPM for 24 hours at room temperature. The water was removed by vacuum filtration over a gulf filter crucible (porosity 4) and the powder was dried at room temperature for 2.5 days and then at 50 ℃ under vacuum (10 mBar) overnight. Finally, the resulting powder was milled using the breaker IKA tube mill control for 1 minute 30 seconds and extracted five additional times with ethyl acetate as previously described. The final powder was dried under vacuum (10 mBar) at 50℃overnight. To ensure removal of all perfume, samples were analyzed by GC pyrolysis and biodegradation measurements were performed according to OECD301F method.
After 60 days of testing, the biodegradability of the exemplary analyzed shells was greater than 40%.
Example 9
Preparation of spray-dried microcapsules
Emulsions a to E having the following compositions were prepared.
Table 10: composition of emulsions A to E and composition of granulated powders A to E after spray drying
1)CapsulTM,Ingredion
2) Maltodextrin 10DE source: roquette
3) Maltose, lehmann & Voss
4) Silica, evonik
5) See Table 11
Table 11: composition of perfume C
1) Swiss Firmenich SA
2) 3- (4-tert-butylphenyl) -2-methylpropanaldehyde, wei Ernie Givaudan SA in Switzerland
3) 1- (octahydro-2, 3, 8-tetramethyl-2-naphthyl) -1-ethanone, U.S. International Flavors & waveguides
4) Swiss Firmenich SA
5) Methyl dihydrojasmonate, firmentich SA, switzerland
6) Swiss Firmenich SA
The components of the polymer matrix (maltodextrin and capsul) are mixed at 45-50 DEG C TM Or capsule, citric acid and tripotassium citrate) is added to the water until completely dissolved.
For emulsion D, free perfume C was added to the aqueous phase.
A microcapsule slurry was added to the resulting mixture. The resulting mixture was then gently mixed at 25 ℃ (room temperature).
The granular powders A to E were prepared by spray drying the emulsions A to E using a Sodeva spray dryer (source: france) with an inlet air temperature set at 215℃and a throughput set at 500mL per hour. The air outlet temperature was 105 ℃. The emulsion prior to atomization is at ambient temperature.
Example 10
Liquid fragrance enhancer composition
A sufficient amount of the example microcapsules were weighed and mixed into the liquid fragrance enhancer to add up the equivalent of 0.2% fragrance.
Table 12: liquid fragrance enhancer composition
1) Decyl alcohol polyether-8; trademark and origin: KLK Oleo
2) Laureth-9; trademark and origin:
3) Plant 2000UP; trademark and origin: BASF (base station architecture)
Different ringing (ringing) gel compositions (compositions 1-6) were prepared according to the following protocol.
In the first step, the aqueous phase (water), solvent (propylene glycol), if present, and surfactant are mixed together at room temperature with a magnetic stirrer at 300rpm for 5 minutes.
In the second step, the linker was dissolved in the hydrophobic active ingredient (fragrance) at room temperature with stirring at 300rpm by a magnetic stirrer. The resulting mixture was mixed for 5 minutes.
The aqueous and oil phases were then mixed together at room temperature for 5 minutes to form a transparent or milky ringing gel.
Example 11
Liquid detergent composition
A sufficient amount of the example microcapsules were weighed and mixed into a liquid detergent to add up the fragrance equivalent to 0.2%.
Table 13: liquid detergent composition
Composition of the components | Concentration [ wt.%) ] |
C 14-17 Sodium secondary alkyl sulfonate 1) | 7 |
C 12-18 And C 18 Unsaturated fatty acids 2) | 7.5 |
C with 7mol EO 12/14 Fatty alcohol polyglycol ether 3) | 17 |
Triethanolamine salt | 7.5 |
Propylene glycol | 11 |
Citric acid | 6.5 |
Potassium hydroxide | 9.5 |
Properase L 4) | 0.2 |
Puradax EG L 4) | 0.2 |
Purastar ST L 4) | 0.2 |
Acrylate/steareth-20 methacrylate structured cross-linked polymer 5) | 6 |
Deionized water | 27.4 |
1) Hostapur SAS 60; the source is as follows: clariant
2) Edenor K12-18; the source is as follows: cognis (Cognis)
3) Genapol LA 070; the source is as follows: clariant
4) The source is as follows: genencor International
5) Aculyn 88; the source is as follows: dow Chemical
Example 12
Unit dose formulation
A sufficient amount of the exemplary microcapsules was weighed and mixed into a unit dose formulation to add up the equivalent of 0.2% fragrance.
The unit dose can be contained in a PVOH (polyvinyl alcohol) film.
Table 14: composition of unit dose
Composition of the components | Concentration [ wt.%)] |
C12-C14 alkyl polyethoxylates | 15 |
C12-C14 alkyl polyethoxylate sulfate monoethanolamine salts | 9.5 |
Straight chain alkylbenzenesulfonic acid | 17 |
Citric acid | 0.5 |
C12-C18 fatty acids | 17 |
Enzymes | 1.2 |
Fluorescent whitening agent | 0.3 |
1, 2-propanediol | 12 |
Glycerol | 9 |
Sodium hydroxide | 1 |
Monoethanolamine | 6 |
PDMS | 2.5 |
Potassium sulfite | 0.2 |
Water and its preparation method | 8.8 |
Totals to | 100 |
Example 13
Powder detergent composition
A sufficient amount of the example microcapsules were weighed and mixed into a powder detergent composition to add up the equivalent of 0.2% perfume.
Table 15: powder detergent composition
Composition of the components | Parts by weight |
Anion (straight-chain alkylbenzene sulfonate) | 20% |
Nonionic (alcohol ethoxylate (5-9 ethylene oxide)) | 6% |
Washing aidAgent (zeolite, sodium carbonate) | 25% |
Silicate salt | 6% |
Sodium sulfate | 35% |
Others (enzyme, polymer, bleach) | 7.5% |
Spray-dried particulate powders A to E | 0.5% |
Example 14
Concentrated universal cleaner compositions
A sufficient amount of the exemplary microcapsules were weighed and mixed into a concentrated general purpose detergent composition to add up to 0.2% fragrance.
Table 16: concentrated universal cleaner compositions
Composition of the components | Amount (wt.%) | Function of |
Ethoxylated alcohols (C9-C11, 8 EO) (1) | 20 | Nonionic surfactant |
Sodium dodecyl benzene sulfonate (2) | 16 | Anionic surfactants |
Cumene sulfonic acid sodium salt (3) | 8 | Hydrotrope (Hydrotrope) |
Methyl chloroisothiazolinone methyl isothiazolinone 3.3:1 (4) | 0.8% | Preservative agent |
Water and its preparation method | 55.9 | Solvent(s) |
1)NeodolTrademark and origin: shell Chemical
2)BiosoftTrademark and origin: stepan Company
3)StepanateTrademark and origin: stepan Company
4)KathonTrademark and origin: dow Chemical Company
All ingredients were mixed together and the mixture was then diluted to 100% with water.
Example 15
Solid flavour enhancer composition
The following compositions were prepared.
Table 17: salt-based solid fragrance enhancer compositions
Composition of the components | Parts by weight |
Sodium chloride | 95 |
Spray-dried particulate powders A to E | 5 |
Table 18: urea-based solid flavour enhancer composition
Composition of the components | Parts by weight |
Urea (bead) | 94 |
Spray-dried particulate powders A to E | 8 |
Bentonite clay | 3 |
Spice | 3 |
Example 16
Shampoo composition
A sufficient amount of exemplary microcapsules were weighed and mixed into the shampoo composition to add up the fragrance equivalent to 0.2%.
Table 19: shampoo composition
1)Ucare Polymer JR-400,Noveon
2)Schweizerhall
3)Glydant,Lonza
4)Texapon NSO IS,Cognis
5)Tego Betain F 50,Evonik
6)Amphotensid GB 2009,Zschimmer&Schwarz
7)Monomuls 90L-12,Gruenau
8) Nipagin Jin Shanna, NIPA
Polyquaternium-10 is dispersed in water. The remaining components of phase a were mixed individually by adding one by one while thoroughly mixing after each addition of the adjuvants. The premix was added to the polyquaternium-10 dispersion and mixed for an additional 5 minutes. Then, the premixed phase B and premixed phase C were added while stirring (Monomuls 90L-12 was heated to melt in Texapon NSO IS). Phase D and phase E were added while stirring. Adjusting the pH with citric acid solution until pH:5.5 to 6.0.
Example 17
Shampoo composition
A sufficient amount of the exemplary microcapsules was weighed and mixed into the shampoo composition to add up the fragrance equivalent to 0.2%.
Table 20: shampoo composition
1) EDETA B powder, BASF
2)Jaguar C14 S,Rhodia
3)Ucare Polymer JR-400,Noveon
4)Sulfetal LA B-E,Zschimmer&Schwarz
5)Zetesol LA,Zschimmer&Schwarz
6)Tego Betain F 50,Evonik
7)Xiameter MEM-1691,Dow Corning
8)Lanette 16,BASF
9)Comperlan 100,Cognis
10)Cutina AGS,Cognis
11)Kathon CG,Rohm&Haas
12 D-panthenol, roche)
A premix of guar hydroxypropyl trimethylammonium chloride and polyquaternium-10 was added to water and tetrasodium EDTA while mixing. When the mixture was homogeneous, naOH was added. Then, the C phase component is added. And the mixture was heated to 75 ℃. Add phase D ingredients and mix until homogeneous. The heating was stopped and the temperature of the mixture was lowered to room temperature. At 45 ℃, add the E phase component while mixing, adjust the final viscosity with 25% NaCl solution, adjust the pH to 5.5-6 with 10% NaOH solution.
Example 18
Rinse-off hair compositions
A sufficient amount of exemplary microcapsules were weighed and mixed into a rinse-off composition to add up to 0.2% fragrance.
Table 21: rinse-off compositions
1)Genamin KDMP,Clariant
2)Tylose H10 Y G4,Shin Etsu
3)Lanette O,BASF
4)Arlacel 165,Croda
5)Incroquat Behenyl TMS-50-PA-(MH),Croda
6)Brij S20,Croda
7)Xiameter MEM-949,Dow Corning
8)Alfa Aesar
The ingredients of phase a were mixed until a homogeneous mixture was obtained. Allow Tylose to dissolve completely. The mixture is then heated to 70-75 ℃. The components of phase B are combined and melted at 70-75 ℃. Ingredients of phase B were then added to phase a with good stirring and mixing continued until the temperature of the mixture was 60 ℃. Then, the ingredients of phase C were added while stirring and kept mixed until the mixture cooled to 40 ℃. The pH value is adjusted to 3.5-4.0 by citric acid solution.
Example 19
Antiperspirant spray anhydrous compositions
A sufficient amount of exemplary microcapsules were weighed and mixed into an antiperspirant spray anhydrous composition to add up to 0.2% fragrance.
Table 22: antiperspirant spray anhydrous compositions
Composition of the components | Amount (wt.%) |
Cyclomethicone 1) | 53.51 |
Myristic acid isopropyl ester | 9.04 |
Silica dioxide 2) | 1.03 |
Quaternary ammonium salt-18-hectorite 3) | 3.36 |
Aluminum hydroxychloride 4) | 33.06 |
1)Dow345Fluid; trademark and origin: dow Corning
2)200; trademark and origin: evonik
3)38, a step of carrying out the process; trademark and origin: elementis Specialities
4) Micro Dry Ultrafine; the source is as follows: reheis
Silica and quaternary ammonium salt-18-hectorite were added to the mixture of isopropyl myristate and cyclomethicone using a high speed stirrer. Once fully swollen, the aluminum chlorohydrate was added in portions with stirring until the mixture was homogeneous and free of caking. The aerosol canister was filled with 25% suspension and 75% propane/butane (2.5 bar).
Example 20
Antiperspirant spray emulsion compositions
An adequate amount of the exemplary microcapsules was weighed and mixed into the antiperspirant spray emulsion composition to add up the fragrance equivalent to 0.2%.
Table 23: antiperspirant spray emulsion compositions
Composition of the components | Amount (wt.%) |
Polysorbate 65 1) (section A) | 0.95 |
Polyglycerol-2-dimer hydroxystearate 2) (section A) | 1.05 |
Cetyl PEG/PPG-10/1 polydimethylsiloxane 3) (section A) | 2.75 |
Cyclomethicone 4) (section A) | 16.4 |
Isopropyl isostearate 5) (section A) | 4.5 |
Phenoxyethanol 6) (section A) | 0.5 |
Ethylhexyl glycerol 7) (section A) | 0.2 |
Benzoic acid C12-15 alkyl esters 8) (section A) | 5.65 |
Silica silylate 9) (section A) | 0.1 |
Sodium methyl paraben 10) (section B) | 0.1 |
Aluminum hydroxychloride 11) (section B) | 20 |
Water (part B) | 44.47 |
Aromatic (C part) | 3.33 |
1) Tween 65; trademark and origin: CRODA
2) Dehypuls PGPH; trademark and origin: BASF (base station architecture)
3) Abil EM-90; trademark and origin: BASF (base station architecture)
4) Dow Corning 345fluid; trademark and origin: dow Corning
5) Crodamol ipis; trademark and origin: CRODA
6) Phenoxyethanol; trademark and origin: LANXESS
7) Sensiva sc 50; trademark and origin: KRAFT
8) Tegosoft TN; trademark and origin: evonik
9) Aerosil R812; trademark and origin: evonik
10 Nipagin mna; trademark and origin: CLARIANT
11 Iocron L; trademark and origin: CLARIANT
The ingredients of parts a and B were weighed separately. The components of part a were heated to 60 ℃ and the components of part B were heated to 55 ℃. The ingredients of part B were poured into a small portion while continuously stirring into a. The mixture was stirred well until room temperature was reached. Then, the component of part C was added. The emulsion is mixed and introduced into an aerosol canister. The propellant is compacted and added.
Aerosol filling: 30% emulsion 70% propane/butane 2.5bar
Example 21
Body fragrance spray composition
An adequate amount of the exemplary microcapsules was weighed and mixed into the antiperspirant fragrance spray composition to add up the fragrance equivalent to 0.2%.
Table 24: body fragrance spray composition
Composition of the components | Amount (wt.%) |
Ethanol 95% | 90.65 |
Triclosan 1) | 0.26 |
Myristic acid isopropyl ester | 9.09 |
1)DP 300; trademark and origin: BASF (base station architecture)
All ingredients were mixed and dissolved according to the order of table 24. The aerosol can was then filled, compacted and propellant (aerosol fill: 40% active solution, 60% propane/butane 2.5 bar) was added.
Example 22
Antiperspirant bead emulsion compositions
An adequate amount of the exemplary microcapsules was weighed and mixed into the antiperspirant bead emulsion composition to add up the fragrance equivalent to 0.2%.
Table 25: antiperspirant bead emulsion compositions
Composition of the components | Amount (wt.%) |
Stearyl alcohol polyether-2 1) (section A) | 3.25 |
Stearyl alcohol polyether-21 2) (section A) | 0.75 |
PPG-15 stearyl ether 3) (section A) | 4 |
Deionized water (part B) | 51 |
50% aqueous solution of aluminum chlorohydrate 4) (section C) | 40 |
Aromatic (part D) | 1 |
1) BRIJ 72; the source is as follows: ICI (inter-cell interference)
2) BRIJ 721; the source is as follows: ICI (inter-cell interference)
3) ARLAMOL E; the source is as follows: UNIQEMA-CRODA
4) LOCRON L; the source is as follows: CLARIAN
Heating part A and part B to 75deg.C respectively; part a was added to part B with stirring and the mixture was homogenized for 10 minutes. The mixture was then cooled under stirring. Part C was slowly added when the mixture reached 45 ℃ and part D was slowly added when the mixture reached 35 ℃ with stirring. The mixture was then cooled to room temperature.
Example 23
Antiperspirant beaded compositions
An adequate amount of the exemplary microcapsules was weighed and mixed into an antiperspirant bead composition to add up the fragrance equivalent to 0.2%.
Table 26: antiperspirant beaded compositions
Composition of the components | Measuring amount |
Water (part A) | 45 |
50% aqueous solution of aluminum chlorohydrate 1) (section B) | 20 |
Denatured alcohol (ethanol 96%) (part B) | 30 |
Cetostearyl alcohol polyether-12 2) (section C) | 2 |
Cetostearyl alcohol polyether-30 3) (section C) | 2 |
Aromatic (part D) | 1 |
1) LOCRON L; the source is as follows: CLARIANT
2) EUMULGIN B-1; the source is as follows: BASF (base station architecture)
3) EUMULGIN B-3; the source is as follows: BASF (base station architecture)
The ingredients of part B were mixed in a container, and then the ingredients of part a were added. Part C is then dissolved into parts a and B. For fragrance, 1 part fragrance was added with 1 part Cremophor RH40, while mixing well.
Example 24
Antiperspirant beaded compositions
An adequate amount of the exemplary microcapsules was weighed and mixed into the antiperspirant bead emulsion composition to add up the fragrance equivalent to 0.2%.
Table 27: antiperspirant bead emulsion compositions
Composition of the components | Amount (wt.%) |
Water (part A) | 50.51 |
Hydroxyethyl cellulose 1) (section A) | 0.71 |
Ethanol 95% (part B) | 40.40 |
1, 2-propanediol (part B) | 5.05 |
Triclosan 2) (section B) | 0.30 |
PEG-40 hydrogenated castor oil 3) (section C) | 3.03 |
1)250H; trademark and origin: ashland
2)DP 300; trademark and origin: BASF (base station architecture)
3)RH 40; trademark and origin: BASF (base station architecture)
Part a was prepared by sprinkling hydroxyethyl cellulose little by little in water while stirring rapidly with a turbine. Stirring was continued until the hydroxyethyl cellulose had fully swelled and gave a clear gel. Then, part B was poured into part a little by little while continuing stirring until the whole was uniform. Add part C.
Example 25
Body fragrance pump of alcohol-free formulation
An adequate amount of the exemplary microcapsules was weighed and mixed into the following composition to add the fragrance equivalent to 0.2%.
Table 28: body fragrance composition
Composition of the components | Amount (wt.%) |
Lactic acid C12-15 alkyl esters 1) | 5 |
Polydimethylsiloxane 2) | 91.6 |
Cetyl lactate 3) | 1 |
Octyl dodecanol 4) | 0.8 |
Triclosan 5) | 0.1 |
Spice | 1.5 |
1) Ceraphyl 41; trademark and origin: ASHLAND
2) DOW CORNING 200 FLUID 0.65cs; trademark and origin: DOW CORNING CORPORATION
3) Ceraphyl 28; trademark and origin: ASHLAND
4) Eutanol G; trademark and origin: BASF (base station architecture)
5)DP 300; trademark and origin: BASF (base station architecture)
All ingredients were mixed according to the order in the table and the mixture was slightly heated to dissolve the cetyl lactate.
Example 26
Body fragrance pump with alcohol formulation
An adequate amount of the exemplary microcapsules was weighed and mixed into the following composition to add the fragrance equivalent to 0.2%.
Table 29: body fragrance composition
Composition of the components | Amount (wt.%) |
Ethanol (part A) | 60 |
PEG-6 caprylic/capric glyceride 1) (section A) | 2 |
Water (part A) | 35.6 |
PEG-40 hydrogenated castor oil 2) (section B) | 0.4 |
Perfume (part B) | 2 |
1) Softigen 767; trademark and origin: CRODA
2)RH 40; trademark and origin: BASF (base station architecture)
The ingredients in part B were mixed together. The ingredients of part a were dissolved in the order in the table and then poured into part B.
Example 27
Talc formulation
Sufficient particles a-E were weighed and mixed into a standard talc base: 100% talc, very slightly characteristic odor, white powder, source: LUZENAC to add up to 0.2% fragrance.
Example 28
Body wash reference
An adequate amount of the exemplary microcapsules was weighed and mixed into the following composition to add the fragrance equivalent to 0.2%.
Table 30: shower gel composition
Composition of the components | Amount (wt.%) | Function of |
Deionized water | 49.350 | Solvent(s) |
EDTA tetrasodium salt 1) | 0.050 | Chelating agent |
Acrylic ester copolymer 2) | 6.000 | Thickening agent |
Sodium C12-C15 Alkanol polyether sulfate 3) | 35.000 | Surface active agent |
Sodium hydroxide 20% aqueous solution | 1.000 | PH regulator |
Cocamidopropyl betaine 4) | 8.000 | Surface active agent |
Methyl chloroisothiazolinone and methyl isothiazolinone 5) | 0.100 | Preservative agent |
Citric acid (40%) | 0.500 | PH regulator |
1) EDETA B powder; trademark and origin: BASF (base station architecture)
2) CARBOPOL AQUA SF-1 polymer; trademark and origin: NOVEON
3) Zetesol AO 328U; trademark and origin: ZSCHIMMER & SCHWARZ
4) TEGO-BETAIN F50; trademark and origin: GOLDSCHMIDT
5) KATHON CG; trademark and origin: ROHM & HASS
The ingredients were mixed and the pH was adjusted to 6 to 6.3 (viscosity: 4500cPo +/-1500cPo (Brookfield RV/Spindle #4/20 RPM)).
Example 29
Shower gel composition
An adequate amount of the exemplary microcapsules was weighed and mixed into the following composition to add the fragrance equivalent to 0.2%.
Table 31: shower gel composition
Composition of the components | Amount (wt.%) | Function of |
Deionized water | 52.40 | Solvent(s) |
EDTA tetrasodium salt 1) | 0.10 | Chelating agent |
Sodium benzoate | 0.50 | Preservative agent |
Propylene glycol | 2.00 | Solvent(s) |
Sodium C12-C15 Alkanol polyether sulfate 2) | 35.00 | Surface active agent |
Cocamidopropyl betaine 3) | 8.00 | Surface active agent |
Polyquaternium-7 4) | 0.20 | Conditioning agent |
Citric acid (40%) | 1.00 | PH regulator |
Sodium chloride | 0.80 | Viscosity modifier |
1) EDETA B powder; trademark and origin: BASF (base station architecture)
2) ZETESOL AO 328U; trademark and origin: ZSCHIMMER & SCHWARZ
3) TEGO-BETAIN F50; trademark and origin: GOLDSCHMIDT
4) MERQUAT 550; trademark and origin: lubrisol
The ingredients were mixed and the pH was adjusted to 4.5 (viscosity: 3000cPo +/-1500cPo (Brookfield RV/Spindle #4/20 RPM)).
Example 30
Shower gel composition
An adequate amount of the exemplary microcapsules was weighed and mixed into the following composition to add the fragrance equivalent to 0.2%.
Table 32: shower gel composition
1) EDETA B powder; trademark and origin: BASF (base station architecture)
2) Texapon NSO IS; trademark and origin: COGNIS
3) MERQUAT 550; trademark and origin: lubrisol
4) DEHYTON AB-30; trademark and origin: COGNIS
5) GLUCAMATE LT; trademark and origin: lubrisol
6) EUPERRAN PK 3000AM; trademark and origin: COGNIS
7) CREMOPHOR RH 40; trademark and origin: BASF (base station architecture)
The ingredients were mixed and the pH adjusted to 4.5 (viscosity: 4000cPo +/-1500cPo (Brookfield RV/Spindle #4/20 RPM)).
Example 31
Hand dishwashing detergent
An adequate amount of the exemplary microcapsules was weighed and mixed into the following composition to add the fragrance equivalent to 0.2%.
Table 33: hand dishwashing detergent compositions
Composition of the components | Amount (wt.%) | Function of |
Straight chain alkylbenzenesulfonic acid (1) | 20 | Anionic surfactants |
Diethanolamide (2) | 3.5 | Foam reinforcing agent |
Sodium hydroxide (50%) (3) | 3.4 | pH regulator/neutralizer |
Secondary alcohol ethoxylates (ethoxolate) (4) | 2.5 | Nonionic surfactant |
Sodium xylene sulfonate | 6.3 | Hydrotropic agent |
Water and its preparation method | 64.3 | Solvent(s) |
1)BiosoftTrademark and origin: stepan Company->
2)NinolTrademark and origin: stepan Company
3)StepanateTrademark and origin: stepan Company
4)TergitolTrademark and origin: dow Chemical Company
Water was mixed with sodium hydroxide and diethanolamide. LAS was added. After neutralization of LAS, the remaining ingredients are added. The pH (=7 to 8) is checked and adjusted if necessary.
Example 32
Toothpaste formulations
A sufficient amount of microcapsule slurry M (prepared according to the protocol disclosed in example 1, except that menthol flavor was encapsulated) was weighed and mixed into the following composition to add the equivalent of 0.2% flavor.
Table 34: toothpaste formulations
1)Tixosil 73
2)Tixosil 43
Example 33
Calcium hydrogen phosphate based toothpaste formulations
A sufficient amount of microcapsule slurry M (prepared according to the protocol disclosed in example 1, except that menthol flavor was encapsulated) was weighed and mixed into the following composition to add the equivalent of 0.2% flavor.
Table 35: toothpaste formulations
Composition of the components | Amount (wt.%) |
Carboxymethyl groupCellulose sodium | 1.2% |
Flavoring agent | 1.2% |
Deionized water/pure water | The balance to the final weight |
Sodium lauryl sulfate | 1.3% |
Glycerol | 20.0% |
Saccharin sodium salt | 0.2% |
Dicalcium phosphate dihydrate | 36.0% |
P-hydroxybenzoic acid methyl ester | 0.2% |
Silica dioxide 1) | 3.0% |
Totals to | 100% |
1)200
Example 34
Alcohol-free mouthwash formulations
A sufficient amount of microcapsule slurry M (prepared according to the protocol disclosed in example 1, except that menthol flavor was encapsulated) was weighed and mixed into the following composition to add the equivalent of 0.2% flavor.
Table 36: mouthwash formulation
Composition of the components | Amount (wt.%) |
Propylene glycol | 10% |
Flavoring agent | 0.240% |
Deionized water/pure water | The balance to the final weight |
Poloxamer 407NF | 0.240% |
Sodium lauryl sulfate | 0.040% |
Sorbitol 70% solution | 10.0% |
Saccharin sodium salt | 0.030% |
Glycerol | 3.0% |
Sodium benzoate | 0.100% |
Sucralose | 0.020% |
Benzoic acid | 0.050% |
Totals to | 100% |
Example 35
Mouthwash formulation
A sufficient amount of microcapsule slurry M (prepared according to the protocol disclosed in example 1, except that menthol flavor was encapsulated) was weighed and mixed into the following composition to add the equivalent of 0.2% flavor.
Table 37: mouthwash formulation
Composition of the components | Amount (wt.%) |
Ethanol 190Proof | 15.0% |
Seasoning material | 0.240% |
Deionized water/pure water | The balance to the final weight |
Poloxamer 407 NF | 0.240% |
Sodium lauryl sulfate | 0.040% |
Sorbitol 70% solution | 10.0% |
Saccharin sodium salt | 0.030% |
Glycerol | 3.0% |
Sodium benzoate | 0.100% |
Sucralose | 0.020% |
Benzoic acid | 0.050% |
Totals to | 100% |
。
Claims (15)
1. A core-shell microcapsule comprising:
a core comprising a hydrophobic material, preferably a perfume oil, and
-a polymeric shell comprising a protein selected from the group consisting of potato protein, chickpea protein, pea protein, algae protein, broad bean protein, barley protein, oat protein, wheat gluten protein, lupin protein and mixtures thereof.
2. The core-shell microcapsule according to claim 1, wherein the polymeric shell comprises a material selected from the group consisting of polyamides, polyureas, polyurethanes, polyesters, polyacrylates, polysiloxanes, polycarbonates, polysulfonamides, urea-formaldehyde polymers, melamine-urea polymers, or melamine-glyoxal polymers, and mixtures thereof.
3. Core-shell microcapsules according to claim 1 or 2, wherein the polymer shell is a polyamide-based shell.
4. A core-shell microcapsule according to claim 3, wherein the polyamide-based shell is obtained from the reaction between an acid chloride and at least one amino compound.
5. A core-shell microcapsule according to claim 3, wherein the polyamide-based shell is obtained from the reaction between an acid chloride and at least two amino compounds.
6. The core-shell microcapsule according to claim 4 or 5, wherein the amino compound is selected from the group consisting of: cystamine, cystamine hydrochloride, cystine hydrochloride, cystine dialkyl ester hydrochloride, m-xylylenediamine, 1, 2-diaminocyclohexane, 1, 4-diaminocyclohexane, polyetheramine, ethylenediamine, diethylenetriamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris- (2-aminoethyl) amine, 3-aminopropyl triethoxysilane, 1, 4-diaminobutane, 2-dimethyl-1, 3-propylenediamine, 1, 3-diaminopentane, 1, 2-diaminopropane, triethylenetetramine, 1, 3-diaminopropane; urea; ethylene urea; aminoguanidine bicarbonate; 1- (2-aminoethyl) imidazolin-2-one; n- (3-aminopropyl) -N-dodecylpropane-1, 3-diamine; n1- (2-aminoethyl) -N1-dodecyl-1, 2-ethylenediamine; aminoethylethanolamine; n1- (3-aminopropyl) propane-1, 3-diamine, polyethylenimine, amino compounds such as L-lysine, L-arginine, L-histidine, L-tryptophan, L-serine, L-glutamine, L-threonine, L-leucine, and/or oligomers and polymers derived therefrom, and mixtures thereof.
7. Core-shell microcapsule according to any of the preceding claims, wherein the protein is selected from the group consisting of potato protein, chickpea protein, pea protein and mixtures thereof.
8. The core-shell microcapsule according to any of claims 4 to 7, wherein the acid chloride is a compound of formula (I),
wherein n is an integer from 1 to 8, preferably from 1 to 6, more preferably from 1 to 4, and
wherein X is (n+1) valent C 2 To C 45 A hydrocarbon group optionally comprising at least one group selected from (i) to (xi),
wherein R is a hydrogen atom or an alkyl group such as methyl or ethyl, preferably a hydrogen atom.
9. The microcapsule core-shell according to any of claims 4 to 8, wherein the polyamide-based shell is obtained from the reaction between an acid chloride and at least one amino compound, and wherein the at least one amino compound is L-lysine.
10. A method of preparing a core-shell microcapsule slurry comprising the steps of:
a) Preparing an oil phase comprising a hydrophobic material, preferably a perfume, to form an oil phase;
b) Dispersing the oil phase obtained in step a) into an aqueous phase to form an oil-in-water emulsion;
c) Performing a curing step to form microcapsules in the form of a slurry;
wherein the polyfunctional monomer is added to the oil phase and/or the water phase, and
Wherein a protein selected from the group consisting of potato protein, chickpea protein, pea protein, algae protein, fava bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof is added to the oil phase and/or the water phase.
11. The method according to claim 10, wherein the polyfunctional monomer is selected from the group consisting of at least one acid chloride, polyisocyanate, polyanhydride, polyepoxide, acrylate monomer, polyalkoxysilane, and mixtures thereof.
12. The method according to claim 10 or 11, wherein the method comprises the steps of:
a) Preparing an oil phase comprising an acid chloride and a hydrophobic material, preferably a perfume, to form an oil phase;
b) Dispersing the oil phase obtained in step a) into an aqueous phase to form an oil-in-water emulsion;
c) Performing a curing step to form microcapsules in the form of a slurry;
wherein at least one amino compound is added to the aqueous phase before the formation of the oil-in-water emulsion and/or to the oil-in-water emulsion obtained after step b), and
wherein a protein selected from the group consisting of potato protein, chickpea protein, pea protein, algae protein, fava bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof is added to the oil phase and/or the water phase.
13. A perfuming composition comprising
(i) The perfume microcapsule as defined in claim 1 to 9, wherein the hydrophobic active comprises a perfume,
(ii) At least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base,
(iii) Optionally, at least one fragrance adjuvant.
14. A consumer product, comprising:
-a personal care active base material
Microcapsules as defined in claims 1 to 9 or perfuming compositions as defined in claim 13,
wherein the consumer product is in the form of a personal care composition.
15. A consumer product, comprising:
-household care or fabric care active base
Microcapsules as defined in claims 1 to 9 or perfuming compositions as defined in claim 13,
wherein the consumer product is in the form of a home care or fabric care composition.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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EP21200666.2 | 2021-10-04 | ||
EP21205885.3 | 2021-11-02 | ||
EP21205885 | 2021-11-02 | ||
PCT/EP2022/076819 WO2023057262A1 (en) | 2021-10-04 | 2022-09-27 | Plant protein-based microcapsules |
Publications (1)
Publication Number | Publication Date |
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CN117897223A true CN117897223A (en) | 2024-04-16 |
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Application Number | Title | Priority Date | Filing Date |
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CN202280058156.8A Pending CN117897223A (en) | 2021-10-04 | 2022-09-27 | Plant protein-based microcapsules |
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CN (1) | CN117897223A (en) |
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