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WO2001020985A1 - Immobilisation de substances actives - Google Patents

Immobilisation de substances actives Download PDF

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Publication number
WO2001020985A1
WO2001020985A1 PCT/NL2000/000603 NL0000603W WO0120985A1 WO 2001020985 A1 WO2001020985 A1 WO 2001020985A1 NL 0000603 W NL0000603 W NL 0000603W WO 0120985 A1 WO0120985 A1 WO 0120985A1
Authority
WO
WIPO (PCT)
Prior art keywords
active substance
carrier material
immobilized
group
phase
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/NL2000/000603
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English (en)
Other versions
WO2001020985A9 (fr
Inventor
Renée Josie Gide VAN SCHIJNDEL
Dogan Sahin Sivasligil
Eddie Westerweele
Jeroen Johannes Gerardus Van Soest
Willem Lenselink
Anton Pieter Johan Van Manen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
PFW Aroma Chemicals BV
Original Assignee
PFW Aroma Chemicals BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by PFW Aroma Chemicals BV filed Critical PFW Aroma Chemicals BV
Priority to AU73235/00A priority Critical patent/AU7323500A/en
Priority to EP00961255A priority patent/EP1229789A1/fr
Publication of WO2001020985A1 publication Critical patent/WO2001020985A1/fr
Anticipated expiration legal-status Critical
Publication of WO2001020985A9 publication Critical patent/WO2001020985A9/fr
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • C11D3/226—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin esterified

Definitions

  • This invention relates to a method for immobilizing active substances.
  • European patent application 0 930 334 discloses a polysaccharide conjugate which is capable of binding cellulose.
  • the conjugate is based on a polysaccharide, which is not modified, and a particle that carries a perfume.
  • the particle is preferably a porous silica particle, into which the perfume can penetrate through diffusion.
  • U.S. Patent 5,667,803 relates to the use of a starch acetate as auxiliary substance in pharmaceutical compacted compositions, mainly tablets.
  • a starch acetate As auxiliary substance in pharmaceutical compacted compositions, mainly tablets.
  • DS degree of substitution
  • the starch acetate it is to be used as disintegrator, filler, binder, or agent for regulating the release of an active substance from a tablet.
  • microparticles consisting of an effective substance in a starch envelope are prepared by preparing an oil-in-water emulsion of the effective substance in a hydrophobic phase and starch in water, including this emulsion in a second hydrophobic phase, and subsequently crosslinking the starch.
  • the second hydrophobic phase can eventually be removed.
  • the invention thus relates to a method for immobilizing an active substance, wherein a mixture is prepared of the active substance and a carrier material in a liquid phase, whereafter the liquid phase is converted to a solid phase, the carrier material being an esterified polysaccharide.
  • highly stable systems are obtained This is understood to mean that it is accomplished that an active substance which is immobilized according to the invention is substantially not released under undesired conditions and is substantially released only under desired conditions.
  • a particularly favorable slowed-release profile can be set. This is also understood to mean that through the immobilization the active substance is protected, so that the chance of breakdown of the active substance through physical or chemical influences is reduced considerably.
  • an active substance immobilized according to the invention will have a prolonged shelf life.
  • it is a great advantage of the manner of immobilization according to the invention that it can be effected very simply. Virtually no (complex) operations need to be performed to obtain the stable system referred to.
  • immobilized active substance refers to a complex of an active substance and a carrier material.
  • the carrier material that is used according to the invention is an esterified polysaccharide.
  • suitable polysaccharides are starch, cellulose, alginates, pectin and combinations thereof.
  • the polysaccharide is starch or cellulose, starch being particularly preferred.
  • esterified starch very high loading degrees are feasible.
  • the starch can originate from any natural starch source. Suitable, among others, is starch coming from potatoes, corn, wheat, and tapioca.
  • granular starch is used.
  • the starch can be wholly or partly gelatinized.
  • Suitable derivatives in this connection are, for instance, (partially) hydrolyzed polysaccharides, oxidized polysaccharides, ionized (both cationic and anionic) and etherified polysaccharides.
  • reaction that is performed starting from native polysaccharide to obtain any one of the derivatives mentioned can also be performed with the polysaccharide already esterified.
  • the esterified polysaccharide is preferably biodegradable.
  • a biodegradable material is understood to mean a material that has the property of being broken down within a relatively short time into substances that are preferably soluble in water and non-toxic. The breakdown can take place inter alia through hydrolytic cleavage, under the influence of light, air, water and/or microorganisms occurring in nature.
  • the esterification proper can be carried out in any known manner.
  • the polysaccharide can, for instance, be subjected to a reaction with an acid anhydride, which provides the desired ester group, in aqueous, slightly alkaline medium.
  • suitable esterification reactions are to be found in R.L. Whistler, E.F. Paschall, "Starch Chemistry and Technology", vol. 1 & 2 (1965), Academic Press Inc.
  • the esterification is preferably carried out so as to yield a degree of substitution (DS) at which the esterified polysaccharide is not soluble or poorly soluble in water. In view of this criterion, the desired degree of substitution depends on the nature of the ester group.
  • the value of the degree of substitution can be between 0.05 and a DS corresponding to a complete substitution, and preferably, in particular, between 0.1 and 2.7.
  • the degree of substitution is preferably slightly higher, viz. between 0.3 and 3, preferably between 0.3 and 2.7. It has been found that the release rate of hydrophilic active substances is higher at a relatively high DS, while the release rate of hydrophobic active substances is higher at a relatively low DS.
  • Suitable ester groups that can be introduced are inter alia acetate groups, propionate groups, butyrate groups, alkyl succinate groups, in which the alkyl group contains from 1 to 16 carbon atoms, benzoate groups, and ester groups which are derived from carboxylic acids having from 1 to 18 carbon atoms, such as saturated and monounsaturated or polyunsaturated fatty acids.
  • an acetate ester of a polysaccharide is used, because an active substance can be immobilized with it in a particularly stable manner.
  • the active substance which is immobilized according to the invention can be selected from inter alia medicines (for instance hormones, antiinflammatory agents, insulin, chemotherapeuticals, antibiotics, vaccines and the like), plant protection agents (such as atachloride), paramagnetic substances, catalysts, organic reactants, pheromones, lures, cosmetic actives, washing active substances, disinfectants, fabric conditioning actives, hair conditioning actives, colorants, fragrance, flavor, and nutrients (for instance vitamins, fats, proteins, pep tides, etc.).
  • medicines for instance hormones, antiinflammatory agents, insulin, chemotherapeuticals, antibiotics, vaccines and the like
  • plant protection agents such as atachloride
  • an active substance is used which is soluble or dispersible in a hydrophobic phase.
  • the active substance is an odorous substance or fragrance.
  • fragrance is understood to mean a compound which releases a particular desired odor.
  • Fragrance is also understood to mean a mixture of compounds which is so composed that the odors of the different components of the mixture jointly release a pleasant or desired odor.
  • Examples of compounds that can be used, alone or in combination, as fragrance are natural oils, vegetable and animal extracts, synthetic oils, alcohols, aldehydes, ketones, esters, lactones, ethers, hydrocarbons, nitriles and other classes of chemical compounds. Fragrance can be used to impart to the environment, or other compounds or compositions, a modified, different or enhanced odor.
  • a liquid phase can be formed.
  • a very homogeneous mixture can be obtained, for instance by stirring.
  • a solid phase can be formed, in which the active substance is immobilized on the carrier material.
  • a solution or dispersion of the carrier material and the active substance in a suitable solvent so that the liquid phase is formed by the solvent.
  • the solvent By evaporating the solvent, the solid phase can be obtained, in which the active substance is immobilized on the carrier material.
  • Suitable solvents can be obtained depending on the nature of the carrier material and the active substance.
  • the solvent has a relatively low boiling point. Examples of solvents that can be used are acetone, diethyl ether, dichloromethane, ethanol, methanol and isopropanol. Incidentally, it is also possible to combine the two possibilities and to prepare a melt of the carrier material and the active substance in the presence of a small amount of a solvent, such as the solvents mentioned earlier.
  • small particles, such as microspheres, of immobilized active substance can be prepared by making use of the solvent evaporation method, known per se. It involves the preparation of an emulsion of the above-mentioned liquid phase.
  • the additional liquid that is needed for that purpose is preferably water, so that an oil-in-water emulsion is obtained.
  • a suitable emulsifier for instance polyethylene glycol, can be used.
  • This emulsion is subsequently dried, whereby the intended particles are formed. These can be isolated by, for instance, centrifugation.
  • the active substance is included together with the carrier material in the first hydrophobic phase.
  • Suitable materials for use as first and second hydrophobic phase can be simply found by one skilled in the art on the basis of the Dutch patent application mentioned in combination with his own expert knowledge.
  • a gaseous active substance is immobilized on the above-described carrier material.
  • the carrier material can be employed in a liquid phase. This phase can be obtained by heating the carrier material or by dissolving or dispersing it in a suitable solvent. If desired, after immobilization of the gaseous active substance, the liquid phase can be converted to a solid phase by cooling or removing the solvent. It is also possible to immobilize the gaseous active substance by contacting it with the carrier material in solid form.
  • the present carrier material is highly suitable for capturing odorous substances.
  • fabric that has an unpleasant smell can be treated with the carrier material, as described above, so that the odorous substance spreading the undesired odor is immobilized on the carrier material. What is thus achieved is that the odor is reduced, at least is less perceptible.
  • the odorous substance that is captured can be in the solid, liquid or gaseous phase. It has been found that when the odorous substance is in the gaseous form, it can be captured by the carrier material in solid form.
  • the carrier material can be used in a liquid phase to absorb the odorous substance. After optional drying or cooling, the solid, immobilized active substance can be simply removed.
  • the invention also relates to the use of an esterified polysaccharide for fixing or immobilizing an active substance, the active substance being preferably an odorous substance.
  • This embodiment of the invention can be suitably used for removing numerous unpleasant odors, for instance caused by body fluids, (armpit) deodorants, personal care products, such as (incontinence) diapers, sanitary napkins, panty-liners, tissues, (paper) napkins or towels, and toilet paper, air fresheners, space deodorants, cat litter.
  • personal care products such as (incontinence) diapers, sanitary napkins, panty-liners, tissues, (paper) napkins or towels, and toilet paper, air fresheners, space deodorants, cat litter.
  • a product such as (incontinence) diapers, sanitary napkins, panty-liners, tissues, paper napkins or towels, toilet paper or cat litter, can be provided with the carrier material according to the invention, so that in use the products spread less unpleasant odors.
  • the degree of loading that can be achieved according to the invention is partly dependent on the nature of the carrier material, the active substance and the application. Usually, loading will be between 0.1 and 99% by weight, in particular between 1 and 50% by weight, based on the total weight of dry matter of the carrier material.
  • the solid, immobilized active substance which may or may not be modified as described above, can be processed to form a powder, for instance by grinding.
  • the particle size of the powder can be selected depending on the intended application of the immobilized active substance. It is also possible to use the immobilized active substance in larger forms. Such forms can be obtained by the use of conventional polymer shaping techniques such as extrusion, including film and foil extrusion, injection molding, pressing or vacuum drawing.
  • a chemical or physical modification can be performed on the surface of the carrier material.
  • suitable modifications are partial hydrolysis of the carrier material, crosslinking of the carrier material and ionization of the carrier material, and combinations thereof. It will be clear to one skilled in the art that a variety of modifications known per se are eligible under given circumstances.
  • Partial hydrolysis of the carrier material leads to the immobilized active substance acquiring a more hydrophilic character, which may be desirable when applications in aqueous medium are contemplated.
  • the hydrolysis can be carried out, for instance, by suspending particles of the carrier material in water.
  • a small amount (0.1 - 2% by weight, based on the weight of the particles) of surfactant, such as sodium dodecylsulfate or an alkyl (poly)glucoside can be added.
  • the hydrolysis can be accelerated by changing the pH of the suspension or raising the temperature. Preferably, work is done at a pH between 8 and 13 and a temperature between 20 and 40°C.
  • Crosslinking of the surface of the particles can be carried out to make the immobilized active substance less soluble in water. This may be desired after a partial hydrolysis or other modification has been carried out.
  • crosslinking is used in combination with a partial hydrolysis, an immobilized active substance is obtained which does not dissolve in water but can be very well incorporated in water, for instance in the form of a suspension.
  • crosslinking leads to the active substance being retained particularly well by the carrier material.
  • Crosslinking can be carried out by a reaction with a suitable crosslinking agent, such as trisodium phosphate or epichlorohydrin.
  • a suspension is prepared of the particles in water, optionally in the presence of a small amount (0.1 - 2% by weight, based on the weight of the particles) of surfactant, such as sodium dodecylsulfate or an alkyl (poly)glucoside, to which the crosslinking agent is added in an amount of 0.5-3% by weight, based on the weight of the particles.
  • a small amount (0.5 - 5% by weight, based on the weight of the particles) of a base, for instance NaOH or KOH is added.
  • a base for instance NaOH or KOH
  • the interaction of the immobilized active substance with the environment can be set. What can thus be achieved is, for instance, that the immobilized active substance adheres well to other materials, such as fabric.
  • the dispersibility of the immobilized active substance can be positively influenced.
  • the provision of positively or negatively charged groups at the surface can in principle be carried out in any known manner for introducing charged groups into a polysaccharide material. Examples of suitable methods are described inter alia in R.L. Whistler, E.F. Paschall, "Starch Chemistry and Technology", vol. 1 & 2 (1965), Academic Press Inc. Quaternary ammonium groups and carboxyl or phosphate groups are preferred.
  • the active substance can be released to a target environment by chemical, physical or enzymatic influences. Normally, these influences will (partially) break down or modify the carrier material, such that the active substance is liberated.
  • the active substance can, for instance, be released into the digestive tract under the influence of the prevailing conditions in the various organs (pH, enzymes).
  • the sensitivity of carrier material can be adapted by starting from a different esterified polysaccharide derivative.
  • the release In laundering agents, the release can be promoted by temperature increase or, again, by pH or enzyme influences.
  • the release On or in cultivated soil or potting soil, the release can be accomplished by hydrolysis or action of salts. In reaction mixtures, the release can also be accomplished by the influence of, for instance, electric current or pH adjustment.
  • the immobilized active substance can be used in various applications. Examples include washing agents, fabric softeners, cleaning agents (such as cleaners, detergents, disinfectants, washing-up agents, dish-washing agents, rinsing agents, bleaching agents, and toilet cleaners), fabric conditioners, fabric sprays, ironing aids, tumble dryer additions, optical whiteners, odor masking agents, personal care products, fertilizers, foods, flavors, pharmaceutical agents, tissues, cosmetics (such as perfumes, colognes, bath and shower products, shampoos, hair conditioning products, skin care products, sun screens, creams, lotions, aerosols, and soaps), soil improvers, plant protection agents (against fungi, bacteria, insects, mites, nematodes and the like), covering layers or coatings, paints, inks, organic reactants (hydrogen peroxide), catalysis, and diagnostics.
  • cleaning agents such as cleaners, detergents, disinfectants, washing-up agents, dish-washing agents, rinsing agents, bleach
  • Example 1 immobilization of a fragrance on a carrier material
  • Paselli acetate (10 g) is dissolved in a mixture of fragrance (5 g) and acetone (5 g), optionally with heating (50°C). Next, the volatile solvent acetone is removed by heating the material at 80°C. After cooling, a hard brittle material having a fragrance loading of about 33% by weight is obtained. The material is ground, optionally cryogenically, to form a powder.
  • Paselli acetate (10 g) is dissolved in a mixture of fragrance (5 g) and acetone (5 g), optionally with heating (50°C). Next, a thin film is formed of Paselli acetate/fragrance by pouring the solution onto glass and allowing the volatile solvent acetone to evaporate.
  • Paselli acetate (10 g) is dissolved or suspended in fragrance (5 g) and heated in a closed reactor at 105°C for 2 hours. After cooling, a hard brittle material having a fragrance loading of about 33% is obtained.
  • the material is ground, optionally cryogenically, to form a powder.
  • D. Paselli acetate powder (500 mg) is brought into a saturated atmosphere of fragrance. Depending on the absorption time and the temperature, the loading can be set, see also Fig. 4. The material is ground, optionally cryogenically, to form a powder.
  • a combination of hydrolysis and crosslinking is carried out in water. Paselli acetate/fragrance powder (10 g) is suspended in 50 g water with
  • Paselli acetate/fragrance powder (15 g) is suspended in 250 g water with 20 mg SDS (sodium dodecylsulfate).
  • SDS sodium dodecylsulfate
  • TSTP trisodium triphosphate
  • FIG. 1 gives the release profiles of a yes- (a) and no- (b) immobilized fragrance mixture (ACB 56SE) applied to fabric.
  • the figure clearly shows differing release behavior.
  • the fragrance mixture is immobilized on a carrier material consisting of Paselli acetate having a DS of 3.
  • FIG. 2 gives the release profiles of three immobilized fragrances, viz., Linalool (a), Tilianol Super (b) and Hydroxycitronellal (c).
  • the figure clearly shows that the fragrances exhibit a mutually different release behavior.
  • the fragrances are immobilized on a carrier material consisting of Paselli acetate having a DS of 3.
  • Figure 3 gives the release profiles of Jasmacyclene, immobilized on different carrier materials consisting of Paselli acetate with a DS of 1.0 (a), 1.7 (b) and 3 (c). The figure clearly shows that the active substance exhibits a lower release rate at a higher degree of substitution.
  • Figure 4 gives the absorption behavior at room temperature for the fragrance Frutalone on a powdered Paselli acetate carrier material with a DS of 3.
  • the amount of carrier material (0.1 gram (a) or 0.5 gram (b)) that is present in the saturated fragrance vapor has an influence on the absorption rate.
  • Figure 5 shows the adhesion, i.e. the percentage of the total fragrance that has adhered to the fabric during washing, for a few different modifications and a control experiment with normal, i.e. non-immobilized, Tonalid. The figure shows that the adherence of the fragrance increases due to the above-described immobilization and modifications.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
  • Fats And Perfumes (AREA)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un procédé d'immobilisation d'une substance active consistant à préparer un mélange contenant cette substance active et une substance support dans une phase liquide, puis à convertir cette phase liquide en une phase solide, ladite substance support étant un polysaccharide estérifié. L'invention concerne également l'utilisation d'un polysaccharide estérifié pour fixer ou immobiliser des substances actives, et notamment des substances odorantes.
PCT/NL2000/000603 1999-08-30 2000-08-30 Immobilisation de substances actives Ceased WO2001020985A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU73235/00A AU7323500A (en) 1999-08-30 2000-08-30 Immobilization of active substances
EP00961255A EP1229789A1 (fr) 1999-08-30 2000-08-30 Immobilisation de substances actives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL1012933A NL1012933C2 (nl) 1999-08-30 1999-08-30 Immobilisatie van actieve stoffen.
NL1012933 1999-08-30

Publications (2)

Publication Number Publication Date
WO2001020985A1 true WO2001020985A1 (fr) 2001-03-29
WO2001020985A9 WO2001020985A9 (fr) 2002-09-12

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL2000/000603 Ceased WO2001020985A1 (fr) 1999-08-30 2000-08-30 Immobilisation de substances actives

Country Status (4)

Country Link
EP (1) EP1229789A1 (fr)
AU (1) AU7323500A (fr)
NL (1) NL1012933C2 (fr)
WO (1) WO2001020985A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1923455A2 (fr) 2003-02-18 2008-05-21 Novozymes A/S Compositions détergents

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4962623A (fr) * 1972-10-18 1974-06-18
US4230687A (en) * 1978-05-30 1980-10-28 Griffith Laboratories U.S.A., Inc. Encapsulation of active agents as microdispersions in homogeneous natural polymeric matrices
WO1992011083A1 (fr) * 1987-09-28 1992-07-09 Redding Bruce K Jr Procede et appareil servant a fabriquer des microcapsules
EP0512693A1 (fr) * 1991-04-10 1992-11-11 Andaris Limited Préparation d'agents diagnostiques
EP0691398A1 (fr) * 1994-07-08 1996-01-10 Unilever N.V. Procédé de fabrication de capsules de polymère

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4962623A (fr) * 1972-10-18 1974-06-18
US4230687A (en) * 1978-05-30 1980-10-28 Griffith Laboratories U.S.A., Inc. Encapsulation of active agents as microdispersions in homogeneous natural polymeric matrices
WO1992011083A1 (fr) * 1987-09-28 1992-07-09 Redding Bruce K Jr Procede et appareil servant a fabriquer des microcapsules
EP0512693A1 (fr) * 1991-04-10 1992-11-11 Andaris Limited Préparation d'agents diagnostiques
EP0691398A1 (fr) * 1994-07-08 1996-01-10 Unilever N.V. Procédé de fabrication de capsules de polymère

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 81, no. 22, 2 December 1974, Columbus, Ohio, US; abstract no. 140875m, page 289; XP002137793 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1923455A2 (fr) 2003-02-18 2008-05-21 Novozymes A/S Compositions détergents

Also Published As

Publication number Publication date
AU7323500A (en) 2001-04-24
EP1229789A1 (fr) 2002-08-14
NL1012933C2 (nl) 2001-03-01
WO2001020985A9 (fr) 2002-09-12

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