DK2935457T3 - Aktivstof af mikropartikler - Google Patents

Aktivstof af mikropartikler Download PDF

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Publication number
DK2935457T3
DK2935457T3 DK13818265.4T DK13818265T DK2935457T3 DK 2935457 T3 DK2935457 T3 DK 2935457T3 DK 13818265 T DK13818265 T DK 13818265T DK 2935457 T3 DK2935457 T3 DK 2935457T3
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Denmark
Prior art keywords
microparticles
hase
carbon atoms
acrylic copolymer
aqueous solution
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DK13818265.4T
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English (en)
Inventor
Jean-Marc Suau
Olivier Guerret
Clémentine Champagne
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Coatex Sas
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5026—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poly(lactide-co-glycolide)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/08—Simple coacervation, i.e. addition of highly hydrophilic material
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/01—Hydrocarbons
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
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    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/10—Homopolymers or copolymers of methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
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    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
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    • C08L91/06—Waxes
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/009—Non common dispersing agents polymeric dispersing agent
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    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/18—Hydrocarbons
    • C11D3/181—Hydrocarbons linear
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2093—Esters; Carbonates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
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    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
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    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/12—Processes in which the treating agent is incorporated in microcapsules
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    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
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    • D06P1/0004—General aspects of dyeing
    • D06P1/0016—Dye baths containing a dyeing agent in a special form such as for instance in melted or solid form, as a floating film or gel, spray or aerosol, or atomised dyes
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
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Claims (17)

1. Polymeromsluttede mikropartikler, omfattende: a. mindst én acrylcopolymer af HASE-typen, omfattende: - mindst én anionisk monomer, som har en polymeriserbar vinylfunktion og en carboxylgruppe; - mindst én ikke-ionisk hydrofob monomer, som har en polymeriserbar vinylfunktion; og - mindst én oxyalkyleret associativ makromonomer, som har en polymeriserbar vinylfunktion og en hydrofob kulhydratkæde, b. mindst ét fast-flydende-fasevekselmateriale, som har en faseovergangstemperatur, som varierer fra 20 til 90°C ; og c. mindst ét aktivstof.
2. Mikropartikler ifølge krav 1, hvor faseovergangsmaterialet er udvalgt fra voks af naturlig eller syntetisk oprindelse.
3. Mikropartikler ifølge et af de foregående krav, hvor acrylcopolymeren af HASE-typen i forhold til copolymerens samlede vægt omfatter: - fra 20 til 65 vægt% af mindst én anionisk monomer, som har en polymeriserbar vinylfunktion og en carboxylgruppe; - fra 35 til 75 vægt% af mindst én ikke-ionisk hydrofob monomer, som har en polymeriserbar vinylfunktion; og - fra 0,5 til 15 vægt% af mindst én oxyalkyleret associativ makromonomer, som har en polymeriserbar vinylfunktion og en hydrofob kulhydratkæde.
4. Mikropartikler ifølge krav 1, 2 eller 3, hvor den mindst én oxyalkylerede associative makromonomer af acrylcopolymeren af HASE-typen har formelen (I): (I) R-A-R' hvor: - A står for en polymerkæde: - m alkylenoxidenheder med formelen -CH2CHR1O-, hvor Ri står for en alkyl-gruppe, der omfatter 1 til 4 kulstofatomer, og m varierer fra 0 til 150, - p alkylenoxidenheder med formelen -CH2CHR20-, hvor R2 står for en alkyl-gruppe, der omfatter 1 til 4 kulstofatomer, og m varierer fra 0 til 150, - n ethylenoxidenheder med n, varierer fra 0 til 150, hvor m+n+p >4, og hvor alkylenoxidenheder med formelen -CH2CHR-|0-, alkylenoxidenheder med formelen -CH2CHR20- og ethylenoxidenhederne er blokformede, alternerende eller statisk udformede; - R står for et radikal, som indeholder en polymeriserbar, umættet funktion, der tilhører gruppen af acryl-, methacryl-, malein-, itacon-, crotonestere; og - R' står for en lineær, forbundet eller forgrenet kulhydratkæde, som omfatter fra 6 til 40 kulstofatomer eller en substitueret eller ikke-substitueret cycloal-kyl- eller arylgruppe, som omfatter fra 6 til 100 kulstofatomer.
5. Mikropartikler ifølge krav 4, hvor acrylcopolymeren af HASE-typen omfatter mindst én oxyalkyleret associativ makromonomer med formelen (I), hvor n varierer fra 15 til 150.
6. Mikropartikler ifølge et af kravene 4 eller 5, hvor funktionen R' af den oxyalkylerede associative makromonomer med formelen (I) har en lineær, forbundet eller forgrenet kulhydratkæde, som omfatter fra 8 til 20 kulstofatomer.
7. Mikropartikler ifølge et af kravene 4 til 6, hvor den oxyalkylerede associative makromonomer med formelen (I) er således, at: - m og p står hver især for 0, - n varierer fra 15 til 150, - R står for et radikal, som indeholder en polymeriserbar, umættet funktion, der tilhører gruppen af acryl- og methacrylestere, og - FT står for en lineær kulhydratkæde, som omfatter fra 8 til 18 kulstofatomer eller en forbundet eller forgrenet alkylkæde, som omfatter fra 12 til 20 kulstofatomer.
8. Mikropartikler ifølge et af kravene 1 til 7, som i forhold til mikropartiklernes samlede vægt omfatter: a. fra 1 til 20 vægt% af den mindst én acrylcopolymer af HASE-typen; b. fra 4 til 95 vægt% af mindst ét faseovergangsmateriale, som er udvalgt fra voks af naturlig eller syntetisk oprindelse; og c. fra 4 til 95 vægt% af mindst ét aktivstof, der er udvalgt blandt parfumer eller duftmolekyler.
9. Vandig dispersion, omfattende mikropartikler ifølge et af de foregående krav.
10. Anvendelse af mikropartikler ifølge kravene 1 til 8 eller vandige dispersioner af mikropartikler ifølge krav 9 for at frigøre et aktivstof som reaktion på en ændring af pH-værdien, en temperaturændring og/eller friktioner.
11. Anvendelse af mikropartikler ifølge kravene 1 til 8 eller vandige dispersioner af mikropartikler ifølge krav 9 til fremstilling af kosmetiske produkter, agrokemiske produkter, malinger, tekstiler, detergenter, papirprodukter.
12. Fremgangsmåde til fremstilling af en vandig dispersion af polymeromsluttede mikropartikler, som omfatter følgende trin: a) fremstilling af en vandig opløsning, som omfatter: - mindst én acrylcopolymer af FIASE-typen, som opløses i den vandig opløsning ved hjælp af en base, hvor acrylcopolymeren af HASE-typen omfatter: - mindst én anionisk monomer, som har en polymeriserbar vinylfunktion og en carboxylgruppe; - mindst én ikke-ionisk hydrofob monomer, som har en polymeriserbar vinylfunktion; og - mindst én oxyalkyleret associativ makromonomer, som har en polymeriser-bar vinylfunktion og en hydrofob kulhydratkæde; - mindst ét aktivstof; og - mindst ét fast-flydende-fasevekselmateriale, som har en faseovergangstemperatur, som varierer fra 20 til 90°C, hvor det fast-flydende-fasevekselmateriale forefindes, eller er indføres i den vandige opløsning med en temperatur, der er større end faseovergangstemperaturen; og b) coacervation af acrylpolymeren af HASE-typen for at nå til de vandige dispersioner af mikropartikler.
13. Fremgangsmåde ifølge krav 12, hvor trin a) udføres i de følgende trin: a1) fremstilling af en vandig opløsning, som omfatter acrylcopolymeren af HASE-typen, der er opløst ved hjælp af en base; a2) fremstilling af en blanding, som omfatter aktivstoffet og faseveksel materialet, hvor blandingen fremstilles ved en temperatur, der er højere end faseovergangstemperaturen af fasevekslingsmaterialet; og a3) indføring af den i trin a2) opnåede blanding i den i trin a1) opnåede vandige opløsning.
14. Fremgangsmåde ifølge krav 12, hvor trin a) udføres i de følgende trin: a1) fremstilling af en vandig opløsning, som omfatter en base, mindst ét aktivstof, mindst ét fasevekselmateriale og mindst én acrylcopolymer af HASE-typen; og a2) opvarmning af den i trin a1) opnåede vandige opløsning til en temperatur, der er større end overgangstemperaturen af faseveksel materialet.
15. Fremgangsmåde ifølge et hvilket som helst af kravene 12 til 14, hvor kvantiteten af den base, som anvendes til at opløse copolymeren er, således at pH-værdien af opløsningen er større end eller lig med 6,5.
16. Fremgangsmåde ifølge et hvilket som helst af kravene 12 til 15, hvor trin b) udføres ved at tilsætte en syre, i en sådan mængde, at pH-værdien af dis persionen er mindre end eller lig med 6,5.
17. Fremgangsmåde til fremstilling af faste polymeromsluttede mikropartikler, som omfatter følgende trin: a) fremstilling af en vandig dispersion af mikropartikler ifølge et af kravene 12 til 16; b) tørring af den vandige dispersion.
DK13818265.4T 2012-12-20 2013-12-09 Aktivstof af mikropartikler DK2935457T3 (da)

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PCT/FR2013/052996 WO2014096622A1 (fr) 2012-12-20 2013-12-09 Microparticules d'agent actif

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US10793686B2 (en) * 2018-12-07 2020-10-06 National Chung-Shan Institute Of Science And Technology Preparation method of vinyl ester resin for optimizing heat-release during curing
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US20140178485A1 (en) 2014-06-26
ES2611913T3 (es) 2017-05-11
KR20150097720A (ko) 2015-08-26
WO2014096622A1 (fr) 2014-06-26
FR3000084A1 (fr) 2014-06-27
EP2935457A1 (fr) 2015-10-28

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