WO2000051724A1 - Procede de protection et/ou de liberation controlee d'ingredients actifs - Google Patents

Procede de protection et/ou de liberation controlee d'ingredients actifs Download PDF

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Publication number
WO2000051724A1
WO2000051724A1 PCT/US2000/004908 US0004908W WO0051724A1 WO 2000051724 A1 WO2000051724 A1 WO 2000051724A1 US 0004908 W US0004908 W US 0004908W WO 0051724 A1 WO0051724 A1 WO 0051724A1
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Prior art keywords
molecular sieve
angstroms
active ingredient
pore diameter
composition
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PCT/US2000/004908
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English (en)
Inventor
Barry Stoddart
Gordon Robert Davison
Philip Frank Souter
Martin Ian James
Alfred Tsz-Chun Wong
Andrew Russell Graydon
Emmanuel Narinx
Graeme Duncan Cruickshank
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The Procter & Gamble Company
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Priority to AU37081/00A priority Critical patent/AU3708100A/en
Publication of WO2000051724A1 publication Critical patent/WO2000051724A1/fr

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    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/143—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26—Aluminium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • 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
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • 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
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/10—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate
    • B01J20/16—Alumino-silicates
    • B01J20/18—Synthetic zeolitic molecular sieves
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
    • A61L2300/602—Type of release, e.g. controlled, sustained, slow

Definitions

  • the present invention relates to a compositions and methods for protecting environmentally-sensitive or hazardous active ingredients.
  • the invention also relates to compositions and methods for the controlled-release of active ingredients in response to an external trigger.
  • detergency enzymes can be deleteriously effected by interaction with bleaches, sequesterants, acids and bases, surfactants and air; perfumes, bleach activators and bleach catalysts can be deleteriously effected by interaction with bleaches; cationic surfactants can be deleteriously effected by interaction with anionic surfactants; fluorescers can be deleteriously effected by interaction with bleaches and cationic surfactants; and suds- suppressors can be deleteriously effected by interaction with surfactants.
  • the consumer acceptability of a product can also be significantly impaired as the result of physical interactions between an active ingredient and other components of a composition. For instance, a speckled detergent containing a water-soluble dye can lose its aesthetic appeal as a result of migration of the dye into the detergent base formula.
  • Controlled release technology offers many possibilities for new oral and parenteral dosage forms, e.g., for masking bitter tasting pharmaceuticals, providing extended release in vivo, or for providing enteric release of drugs.
  • Broadscale consumer applications of controlled release technology outside the medical and agricultural fields are relatively limited at present, however, primarily for reasons of cost as well as technical deficiencies in current technology.
  • the present invention provides novel compositions and methods for protecting environmentally-sensitive or hazardous active ingredients and/or for the controlled release of active ingredients with improved technical performance and cost/benefit ratio.
  • the present invention relates to the use of a large pore molecular sieve having a pore diameter greater than about 8 Angstroms, preferably greater than about 10 Angstroms, as agent for the protection and/or controlled release of an active ingredient.
  • Preferred molecular sieves herein are selected from: a) mesoporous molecular sieves having a pore diameter of at least 13, preferably at least 15, and more preferably at least 20 Angstroms; b) phosphate-containing molecular sieves, especially those selected from aluminophosphates, silicoaluminophosphates, metalloaluminophosphates and metallosilicoaluminophosphates wherein 'metallo' represents an additional metallic element selected from Mg, Ti, Mn, Co, Fe, Ga, and Zn; and c) mixtures therof.
  • M41S mesoporous molecular sieves designated M41S which consist essentially of crystalline, inorganic material exhibiting after calcination an X-ray diffraction pattern with at least one peak at a d-spacing of at least 18 Angstroms.
  • MCM-41 which can be described as a mesoporous molecular sieve consisting essentially of inorganic, porous, crystalline material having, after calcination, a hexagonal arrangement of uniformly-sized pores having a pore diameter of at least about 13 Angstrom and exhibiting a hexagonal electron diffraction pattern that can be indexed with a d, 00 value greater than about 18 Angstrom units.
  • the present invention provides a method of protecting an environmentally-sensitive or hazardous active ingredient comprising physically or chemically sorbing the ingredient within the pores of a large pore molecular sieve having a pore diameter greater than about 8 Angstroms.
  • the invention provides a method for the controlled release of an active ingredient comprising physically or chemically sorbing the ingredient within the pores of a large pore molecular sieve having a pore diameter greater than about 8 Angstroms and releasing the ingredient under diffusion control or in response to an external trigger.
  • compositions toothbrushes Saliva, mouth odors Diapers, babywipes Urine, faeces, body odors Feminine protection products Menses, body odors Shoe inserts Perspiration, body odor Clothing, bedlinen Perspiration Pet treatment Rainwater Pet litter Urine, faeces, pet odor Wound dressings Blood, wound excretion Pharmaceuticals pH, bacteria
  • the present invention also provides a composition comprising an environmentally- sensitive or hazardous active ingredient physically or chemically sorbed within the pores of a large pore molecular sieve having a pore diameter greater than about 8 Angstroms.
  • environmentally-sensitive or hazardous ingredient examples include bleaches and oxidants, bleach activators, bleach catalysts, photoactivators, fabric softening agents, perfumes, flavors, pigments, enzymes, vitamins, skin/hair cosmetics, pharmaceuticals, antimicrobials, fertilizers, explosives, and corrosive materials.
  • compositions will frequently comprise an antagonist for the environmentally-sensitive or hazardous ingredient.
  • environmentally-sensitive ingredients and their specific antagonists include:
  • a controlled-release composition comprising an active ingredient physically or chemically sorbed within the pores of a large pore molecular sieve having a pore diameter greater than about 8 Angstroms and being releasable therefrom by diffusion control or in response to an external trigger.
  • active ingredients suitable for controlled release include bleaches and oxidants, bleach activators, bleach catalysts, photoactivators, fabric softening agents, perfumes, flavors, pigments, enzymes, vitamins, skin/hair cosmetics, pharmaceuticals, antimicrobials, fertilizers, explosives, and corrosive materials.
  • the compositions herein can take various forms including optionally agglomerated particulate solids, membranes, encapsulates, bars, liquids, gels and aerosols.
  • the present invention also provides a variety of consumer and retail products designed for personal, household, industrial and institutional use.
  • compositions herein comprise a large pore molecular sieve in an amount effective for protecting and/or controlling the release of an active ingredient, preferably in an amount of at least about 0.001%, more preferably from about 0.001% to about 20%, and most preferably from about 0.05% to about 10% by weight of composition.
  • the term "large pore molecular sieve” refers to a range of microporous and mesoporous crystalline materials built around an inorganic charged or neutral framework and possessing pores having a relatively uniform size distribution.
  • the pore diameter of the molecular sieves herein should be greater than about 8 Angstroms.
  • Mesoporous molecular sieves of this type can be generally described as crystalline, inorganic materials which exhibit after calcination an X-ray diffraction pattern with at least one peak at a d-spacing of at least about 18 Angstroms.
  • the term 'crystalline' indicates that the molecular sieve has sufficient order to provide, following calcination, a diffraction pattern such as, for example, by X-ray, electron or neutron diffraction with at least one peak
  • the molecular sieve may exist as a mixture of physically distinct phases. Also, defects and imperfections can cause significant deviations from an ideal regular structure. Generally, however, the pore size distribution within a single phase will be within about 25%, usually within about 15% of the average pore size for that phase.
  • the pore diameter of the molecular sieves can be determined in known manner, for example, by transmission electron microscopy (TEM), x-ray diffraction or argon physisorption.
  • TEM is the preferred technique herein.
  • Suitable methods for determining pore diameter by argon physisorption are disclosed in US-A-5,098,684.
  • Molecular sieves suitable for use herein include large pore natural and synthetic zeolites, i.e., molecular sieves based on a crystalline silicate or alumino silicate framework, as well as phosphate-containing molecular sieves and zeolite analogs such as aluminophosphates, silicoaluminophosphates, metalloaluminophosphates and metallosilicoaluminophosphates wherein 'metallo' represents an additional metallic element such as Mg, Ti, Mn, Co, Fe, Ga, or Zn. Large pore silicate molecular sieves (essentially aluminium-free) are also suitable for use herein.
  • zeoilite-type molecular sieves see D.W. Breck, Zeolite Molecular Sieves, Structure, Chemistry and Use, John Wiley & Sons, Inc., New York, 1974.
  • Molecular-sieves of the aluminosilicate variety can be represented by the empirical formula M 2/n O . Al 2 O 3 . ySiO 2 . wH 2 O, where y is 2 or greater, M is the charge balancing cation, such as sodium, potassium, ammonium, magnesium, and calcium, n is the cation valence, and w represents the moles of water contained in the zeolitic voids.
  • the zeolite framework is made up of SiO 4 tetrahedra linked together by sharing of oxygen ions. Substitution of a Group IIIB metal such as Al for Si generates a charge imbalance, necessitating the inclusion of a cation.
  • the structures contain channels or interconnected voids that are occupied by the cations and water molecules.
  • the water may be removed reversibly, generally by the application of heat, which leaves intact the crystalline host structure permeated with micropores that may account for >50% of the microcrystal's volume.
  • dehydration may produce some perturbation of the structure, such as cation movement, and some degree of framework distortion.
  • zeolite structures There are two basic types of zeolite structures: one provides an internal pore system comprising interconnected cage- like voids; the second provides a system of uniform channels which, in some instances, are one-dimensional and in others intersect with similar channels to produce two- or three-dimensional channel systems.
  • the preferred type has two- or three-dimensional channel systems to provide rapid intracrystalline diffusion in adsorption and catalytic applications.
  • Suitable aluminophosphates include those disclosed in US-A-4,310,440 and US-A-4,385,994. These aluminophosphates have essentially electroneutral lattices.
  • US-A-3, 801,704 discloses an aluminophosphate treated in a certain way to impart acidity.
  • compositions comprising crystals having a framework topology after heating at 110 °C or higher giving an X-ray diffraction pattern consistent with a material having pore windows formed by 18 tetrahedral members of about 12-13 Angstroms in diameter are disclosed in US-A-No. 4,880,611.
  • Silicoaluminophosphates of various structures are disclosed in US-A-4,440,871, US-A-3,355,246 (ZK-21) and US-A-3,791,964 (ZK-22).
  • Other disclosures of silicoaluminophosphates and their synthesis include US-A-4,673,559 (two-phase synthesis method); US-A-4,623,527 (MCM 10); US-A-4,639,358 (MCM-1); US-A- 4,647,442 (MCM-2); US-A-4,664,S97 (MCM-4); US-A-4,638,357 (MCM-5); and US-A- 4,632,811 (MCM-3).
  • a method for synthesizing crystalline metalloaluminophosphates is disclosed in US-A- 4,713,227, while an antimonophosphoaluminate and its synthesis are disclosed in US-A- 4,619,818.
  • US-A-4,567,029 discloses metalloaluminophosphates, while titaniumaluminophosphate and its synthesis are disclosed in US-A-4,500,651.
  • Other suitable phosphate-containing molecular sieves include the phosphorus substituted zeolites of CA-A-911,416; CA-A-911,417; and CA-A-911,418.
  • US-A-4,363,748 describes a combination of silica and aluminium-calcium-cerium phosphate as a low acid activity catalyst for oxidative dehydrogenation.
  • GB-A-2,068J53 discloses a combination of silica and aluminium-calcium-tungsten phosphate as a low acid activity catalyst for oxidative dehydrogenation.
  • US-A-4J28,036 discloses an alumina-aluminium phosphate-silica matrix as an amorphous body to be mixed with zeolite for use as cracking catalyst.
  • US-A-3J13,035 teaches improving hardness of aluminosilicate catalysts by treatment with phosphoric acid. The catalysts are amorphous.
  • molecular sieves of the phosphate-containing type preferred for use herein include AlPO 4 -5, AlPO 4 -8, SAPO-5, SAPO-37, VPI-5, Cloverite (an 18-membered ring gallophosphate), and JDF-20.
  • Another class of large pore molecular sieves suitable for use herein are the liquid crystal template-synthesised M41S range of mesoporous molecular sieves reported by C.T. Kresge and co-workers, Nature 359, 710 (1992) and by Beck and co-workers, J. Amer. Chem. Soc. 114, 10834 (1992). See also US-A-5 ,102,643, US-A-5,250,282, US-A- 5,264,203, US-A-5,145,816, US-A-5,098,684, US-A-5,378,440, US-A-5,098,684, US-A- 5,108,725 and US-A-5,057,296.
  • the M41S mesoporous molecular sieves can be described (see US-A- 5,378,440) as inorganic, porous, non-layered crystalline phase materials which exhibit, after calcination, an X-ray diffraction pattern with at least one peak at a d-spacing greater than about 18 Angstrom Units with a relative intensity of 100 and a benzene adsorption capacity of greater than 15 grams benzene per 100 grams of anhydrous crystal at 50 torr and 25 °C.
  • M41S molecular sieves herein are mesoporous molecular sieves which consist essentially of inorganic, porous, crystalline material having, after calcination, a hexagonal arrangement of uniformly-sized pores having a pore diameter of at least about 13 Angstrom and exhibiting a hexagonal electron diffraction pattern that can be indexed with a d 100 value greater than about 18 Angstrom units.
  • Such materials have been given the designation MCM-41 (see US-A-5,378,440).
  • Preferred large pore molecular sieves for use herein have a pore diameter of about 13 Angstroms or greater, more preferably of about 20-200 Angstroms, and most preferably about 30-100 Angstroms. Also preferred molecular sieves herein have surface area of at least about 300 m 2 /g, more preferably at least about 400 m 2 /g and most preferred being at least about 500 m 2 /g. In addition, the molecular sieves preferred for use herein are relatively hydrophobic, being either aluminium-free or having an Si: Al molar ratio of at least about 10:1, preferably at least about 30:1, more preferably at least about 60:1, and especially at least about 100:1
  • the molecular sieves can be used in colloidal or micron-sized form (with a primary particle size of less than about 10 microns, preferably less than about 1 micron, more preferably less than about 0.1 micron) or they can be used as larger sized particles (compositions at risk of inhalation, for example, will generally have a particle size in excess of 10 microns, preferably greater than 15 microns) or they can be shaped or agglomerated into a wide variety of particle sizes.
  • shaped/agglomerated particles can be in the form of a powder, a granule, or a molded product, such as an extrudate having particle size sufficient to pass through a 2 mesh (Tyler) screen and be retained on a 400 mesh (Tyler) screen.
  • the molecular sieve can be extruded before drying or partially dried and then extruded.
  • Suitable binders include inorganic materials such as sodium sulphate, clays, silica and/or metal oxides, such as alumina, titania, and/or zirconia. The latter may be either naturally occurring or in the form of gelatinous precipitates or gels, including mixtures of silica and metal oxides.
  • the clays may be naturally occurring clays, e.g., bentonite and kaolin.
  • Suitable organic binders include cellulose derivatives such as carboxymethyl cellulose and water-soluble polymers such as sodium polyacrylate.
  • Porous matrix suitable herein include silica-alumina, silica-magnesia, silica zirconia, silica-thoria, silica-beryllia, silica-titania as well as ternary compositions such as silica-alumina-thoria, silica-alumina-zirconia, silica-alumina-magnesia and silica-magnesia-zirconia.
  • the active ingredient can be introduced into the pores of the molecular sieve in a number of ways, for example, by incipient wetness impregnation.
  • the molecular sieve is contacted with the active ingredient in liquid or gaseous form or, in the case of solid active ingredients, the molecular sieve is contacted with a solution or colloidal dispersion of the active ingredient.
  • the active ingredient will generally be incorporated in the molecular sieve at a weight ratio (active ingredient:sieve) in the range from about 1 :1000 to about 10:1, preferably from about 1:100 to about 1 :1, more preferably from about 1 :20 to about 1 :4.
  • Preferred active ingredients for incorporation within the molecular sieve include: a) Bleaches and oxidants
  • Suitable bleaching agents herein include chlorine and oxygen-releasing bleaching agents inclusive of hydrogen peroxide, inorganic perhydrates and organic peroxy acids.
  • inorganic perhydrate salts include perborate, percarbonate, perphosphate, persulfate and persilicate salts.
  • the inorganic perhydrate salts are normally the alkali metal salts.
  • Sodium perborate can be in the form of the monohydrate of nominal formula NaBU2H2 ⁇ 2 or the tetrahydrate NaB ⁇ 2H2 ⁇ 2JH2 ⁇ .
  • Alkali metal percarbonates, particularly sodium percarbonate are preferred perhydrates for inclusion herein.
  • Sodium percarbonate is an addition compound having a formula corresponding to 2Na2C ⁇ 3JH2 ⁇ 2, and is available commercially as a crystalline solid.
  • Potassium peroxymonopersulfate is another inorganic perhydrate salt of utility herein.
  • Organic peroxy acids suitable for use herein include aryl peroxyacids such as perbenzoic acid, alkyl peroxyacids such as peracetic acid and pernonanoic acid, cationic peroxyacids, etc, and amide-substituted peroxy acids (see EP-A-0170386).
  • Other organic peroxyacids include diacyl and tetraacylperoxides, especially diperoxydodecanedioc acid, diperoxytetradecanedioc acid, and diperoxyhexadecanedioc acid.
  • Dibenzoyl peroxide is a preferred organic peroxyacid herein.
  • Mono- and diperazelaic acid, mono- and diperbrassylic acid, and N-phthaloylaminoperoxicaproic acid are also suitable herein.
  • oxidants suitable for use as the active ingredient herein include ammonium nitrate, sodium nitrate, sodium chlorate and calcium nitrate.
  • Bleach activators can generally be described as organic peroxyacid bleach precursors, i.e., compounds that react with hydrogen peroxide in a perhydrolysis reaction to produce a peroxyacid, e.g. aryl peroxyacids such as perbenzoic acid, alkyl peroxyacids such as peracetic acid and pernonanoic acid, amide substituted alkyl peroxyacids, cationic peroxyacids, etc.
  • aryl peroxyacids such as perbenzoic acid
  • alkyl peroxyacids such as peracetic acid and pernonanoic acid
  • amide substituted alkyl peroxyacids cationic peroxyacids, etc.
  • peroxyacid bleach precursors may be represented as
  • L is a leaving group and X is essentially any functionality, such that on perhydrolysis the structure of the peroxyacid produced is
  • Suitable peroxyacid bleach precursor compounds typically contain one or more N- or O- acyl groups, which precursors can be selected from a wide range of classes.
  • Suitable classes include anhydrides, esters, imides, lactams and acylated derivatives of imidazoles and oximes. Examples of useful materials within these classes are disclosed in GB-A- 1586789.
  • Suitable esters are disclosed in GB-A-836988, GB-A-864798, GB-A-1147871, GB-A-2143231 and EP-A-0170386.
  • Cationic peroxyacid precursors are described in US- A-4,904,406; US-A-4,751,015; US-A-4,988,451; US-A-4,397,757; US-A-5,269,962; US- A-5,127,852; US-A-5,093,022; US-A-5,106,528; GB-A-1,382,594; EP-A-0475512, EP- A-0458396 and EP-A-0284292; and in JP87-318,332.
  • Bleach catalysts suitable as the active ingredient herein include the manganese triazacyclononane and related complexes (US-A-4246612, US-A-5227084); Co, Cu, Mn and Fe bispyridylamine and related complexes (US-A-5114611); and pentamine acetate cobalt(III) and related complexes(US-A-4810410).
  • the fabric softening agent (sometimes referred to herein as the softener active) is preferably selected from cationic, nonionic, amphoteric and anionic fabric softening agents and mixtures thereof.
  • Typical of the cationic softening agents are the quaternary ammonium compounds or amine precursors thereof as defined hereinafter.
  • Preferred quaternary ammonium fabric softening compounds have the formula
  • each R unit is independently hydrogen, Ci -Cg alkyl, C ⁇ -Cg hydroxyalkyl, and mixtures thereof, preferably methyl or hydroxy alkyl; each Ri unit is independently linear or branched C ⁇ i -C22 alkyl, linear or branched C1 1-C22 alkenyl, and mixtures thereof, R-2 is hydrogen, C1-C4 alkyl, C1-C4 hydroxyalkyl, and mixtures thereof; X is an anion which is compatible with fabric softener actives and adjunct ingredients; the index m is from 1 to 4, preferably 2; the index n is from 1 to 4, preferably 2.
  • DEQA Diester and/or Diamide Quaternary Ammonium
  • Q is -O 2 C- and -NR 2 CO- respectively
  • preferred DEQA compounds being prepared by acylation of an amine such as methyl bis(2-hydroxyethyl)amine, methyl bis(2-hydroxypropyl)amine, methyl (3-aminopropyl) (2-hydroxyethyl)amine, methyl bis(2-aminoethyl)amine, triethanolamine or di(2-aminoethyl)ethanolamine, followed by quaternisation.
  • An example of a preferred fabric softener active is a mixture of DEQA quaternized amines wherein R is methyl; Rl is a linear or branched alkyl or alkenyl chain comprising at least 11 atoms, preferably at least 15 atoms, m is 2, and QR represents a fatty acyl unit (O2CRI ) which is typically derived from a triglyceride source such as tallow, partially hydrogenated tallow, lard, partially hydrogenated lard, vegetable oils and/or partially hydrogenated vegetable oils, such as, canola oil, safflower oil, peanut oil, sunflower oil, corn oil, soybean oil, tall oil, rice bran oil, etc. and mixtures of these oils.
  • O2CRI fatty acyl unit
  • quaternary ammonium softening compounds include methylbis(tallowamidoethyl)(2-hydroxyethyl)ammonium methylsulfate and methylbis(hydrogenated tallowamidoethyl)(2-hydroxyethyl)ammonium methylsulfate; these materials are available from Witco Chemical Company under the trade names Varisoft® 222 and Varisoft® 110, respectively, and N,N-di(tallowoyl-oxy-ethyl)-N,N- dimethyl ammonium chloride, where the tallow chains are at least partially unsaturated (Iodine Value (IV) of the corresponding fatty acid in the range of from 5 to 100).
  • Varisoft® 222 and Varisoft® 110 trade names
  • N,N-di(tallowoyl-oxy-ethyl)-N,N- dimethyl ammonium chloride where the tallow chains are at least partially unsaturated (Iodine Value (IV) of the corresponding
  • quaternary ammonium fabric softening compounds for use herein are cationic nitrogenous salts having two or more long chain acyclic aliphatic Cg-C22 hydrocarbon groups or one said group and an arylalkyl group which can be used either alone or as part of a mixture, for example diamino alkoxylated quaternary ammonium salts and dialkyldimethylammonium salts such as ditallowdimethylammonium chloride, ditallowdimethylammonium methylsulfate, di(hydrogenatedtallow)dimethylammonium chloride, distearyldimethylammonium chloride, and dibehenyldimethylammonium chloride.
  • diamino alkoxylated quaternary ammonium salts and dialkyldimethylammonium salts such as ditallowdimethylammonium chloride, ditallowdimethylammonium methylsulfate, di(hydrogenatedtallow)dimethylam
  • Suitable amine fabric softening compounds for use herein which may be in amine form or cationic form are selected from reaction products of higher fatty acids with a polyamine selected from hydroxyalkylalkylenediamines and dialkylenetriamines (e.g., diethylenetriamine) and mixtures thereof.
  • Preferred compounds of this type are substituted imidazoline compounds, for example Mazamide® 6, sold by Mazer
  • Nonionic fabric softening compounds suitable for use herein, especially in dryer-added embodiments typically have an HLB of from about 2 to about 9, preferably from about 3 to about 7 and are relatively crystalline and higher melting (e.g.,>25°C.)
  • the level of nonionic softener is typically from about 10% to about 50%, preferably from about 15% to about 40%.
  • Preferred nonionic softeners are fatty acid partial esters of polyhydric alcohols, or anhydrides thereof, wherein the alcohol, or anhydride, contains from about 2 to about 18, preferably from about 2 to about 8, carbon atoms, and each fatty acid moiety contains from about 8 to about 30, preferably from about 16 to about 20, carbon atoms.
  • Typical examples of said fatty acids being lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, and behenic acid.
  • such softeners contain from about 1 to about 4, preferably about 2 fatty acid groups per molecule.
  • perfumes are disclosed in U.S. Pat. 5,500,138.
  • perfume includes fragrant substance or mixture of substances including natural (i.e., obtained by extraction of flowers, herbs, leaves, roots, barks, wood, blossoms or plants), artificial (i.e., a mixture of different nature oils or oil constituents) and synthetic (i.e., synthetically produced) odoriferous substances.
  • natural i.e., obtained by extraction of flowers, herbs, leaves, roots, barks, wood, blossoms or plants
  • artificial i.e., a mixture of different nature oils or oil constituents
  • synthetic i.e., synthetically produced odoriferous substances.
  • Such materials are often accompanied by auxiliary materials, such as fixatives, extenders, stabilizers and solvents. These auxiliaries are also included within the meaning of "perfume", as used herein.
  • perfumes are complex mixtures of a plurality of organic compounds.
  • the range of the natural raw substances can embrace not only readily- volatile, but also moderately- volatile and slightly- volatile components and that of the synthetics can include representatives from practically all classes of fragrant substances, as will be evident from the following illustrative compilation: natural products, such as tree moss absolute, basil oil, citrus fruit oils (such as bergamot oil, mandarin oil, etc.), mastix absolute, myrtle oil, palmarosa oil, patchouli oil, petitgrain oil Paraguay, wormwood oil; alcohols, such as farnesol, geraniol, linalool, nerol, phenylethyl alcohol, rhodinol, cinnamic alcohol; aldehydes, such as citral, HelionalTM, alpha-hexyl-cinnamaldehyde, hydroxycitronellal, LilialTM (p-tert-butyl-alpha -methyldihydrocinnamaldehyde), methylnony
  • perfume materials suitable for use herein include geranyl acetate, dihydromyrcenyl acetate, terpinyl acetate, tricyclodecenyl acetate, tricyclodecenyl propionate, 2-phenylethyl acetate, benzyl acetate, benzyl benzoate, styrallyl acetate, amyl salicylate, phenoxyethyl isobutyrate, neryl acetate, trichloromethyl-phenylcarbinyl acetate, p-tertiary butyl-cyclohexyl acetate, isononyl acetate, cedryl acetate, benzyl alcohol, tetrahydrolinalool, citronellol, dimethylbenzylcarbinol, dihydromyrcenol, tetrahydromyrcenol, terpineol, eugenol,
  • Flavorants suitable for use as the active ingredient herein include wintergreen oil, oregano oil, bay leaf oil, peppermint oil, spearmint oil, clove oil, sage oil, sassafras oil, lemon oil, orange oil, anise oil, benzaldehyde, bitter almond oil, camphor, cedar leaf oil, marjoram oil, citronella oil, lavendar oil, mustard oil, pine oil, pine needle oil, rosemary oil, thyme oil, cinnamon leaf oil, and mixtures thereof.
  • Pigments suitable for use as the active ingredient can be organic and/or inorganic. Also included within the term pigment are materials having a low colour or lustre such as matte finishing agents, and also light scattering agents. Examples of suitable pigments are iron oxides, acyglutamate iron oxides, ultramarine blue, D&C dyes, carmine, and mixtures thereof. The pigments can be treated with compounds such as amino acids, silicones, lecithin and ester oils.
  • Enzymes Enzymes suitable herein include bacterial and fungal cellulases such as Carezyme and Celluzyme (Novo Nordisk A/S); peroxidases; lipases such as Amano-P (Amano Pharmaceutical Co.), Ml Lipase R and Lipomax R (Gist-Brocades) and Lipolase R and Lipolase Ultra R (Novo); cutinases; proteases such as Esperase R , Alcalase R , Durazym R and Savinase R (Novo) and Maxatase R , Maxacal R , Properase R and Maxapem R (Gist-Brocades); and ⁇ and ⁇ amylases such as Purafect Ox Am R (Genencor) and Termamyl R , Ban R , Fungamyl R , Duramyl R , and Natalase R (Novo); and mixtures thereof.
  • proteases such as Esperase R , Alcalase R , Durazym
  • Skin/hair cosmetics suitable for use as the active ingredient herein include vitamins and various lipophilic or hydrophobic materials having a moisturising or emollient function including liquids, gels, waxes, particulate solids, etc.
  • Suitable hydrophobic materials and emollients include fatty acids such as lauric and oleic acid, fatty alcohol esters such as isopropyl myristate and isopropyl palmitate, water-insoluble ethers and alcohols such as lauryl alcohol, hexadecyl alcohol, and oleyl alcohol, paraffins and mineral oils, polyorgano silicones and mixtures thereof.
  • fatty acids such as lauric and oleic acid
  • fatty alcohol esters such as isopropyl myristate and isopropyl palmitate
  • water-insoluble ethers and alcohols such as lauryl alcohol, hexadecyl alcohol, and oleyl alcohol
  • paraffins and mineral oils polyorgano
  • Preferred hydrophobic materials include volatile silicone oils.
  • volatile refers to those materials which have a measurable vapor pressure at ambient conditions. Such volatile silicone oils may be cyclic or linear. A description of volatile silicone oils is found in Todd, et al., "Volatile Silicone Fluids for Cosmetics", 91 Cosmetics and Toiletries, 27-32 (1976).
  • Preferred volatile silicone oils include those having from about 3 to about 9 silicon atoms, preferably containing from about 4 to about 5 silicon atoms. Examples include: Dow Corning 344, Dow Corning 345 and Dow Corning 200 (sold by Dow Corning Corporation); 7207 and 7158 (sold by General Electric Company); and SWS-03314 (sold by SWS Silicones Corporation).
  • Preferred skin/hair cosmetics for use herein include vitamins and other cosmetic actives which are known to be sensitive to oxidative degradation such as vitamin A and vitamin E.
  • the actives are introduced into the molecular sieve by, for example, incipient wetness impregnation in an organic solvent phase.
  • the molecular sieve is then incorporated in a skin cosmetic such as a sunscreen, anti-UV cream or other cosmetic emulsion, the active ingredient being releasable therefrom in response to an external trigger such as perspiration.
  • active ingredients suitable for incorporation in the molecular sieve include suds- suppressors, especially materials of the silicone, wax, vegetable and hydrocarbon oil and phosphate ester varieties; fluorescers such as Blankophor MBBH and Tinopal CBS and EMS; photoactivators such as zinc phthalocyanine tri- and tetrasulphonates; pharmaceuticals e.g. actives targeted for release in the lower gastrointestinal tract or for intranasal release; fertilizers such as ammonium nitrate; hazardous materials such as ammonia, fluorine, explosives, caustic alkalis, etc
  • the agents herein can be utilised in a wide variety of product applications, for example, detergent compositions for laundry, dishwashing or hard surface cleaning use; fabric conditioning compositions; perfume, odor-control and aromatherapy compositions; skin and hair cosmetics such as sunscreens, anti-UV creams and the like; oral compositions inclusive of dentifrices, chewing gum and toothbrushes; pharmaceutical compositions for lower-GI and intranasal delivery; fertilizers, etc.

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Abstract

L'invention porte sur l'utilisation d'un tamis moléculaire à larges pores de plus d'environ 8Å comme agent de protection et/ou de libération contrôlée d'ingrédients actifs tels que des agents de blanchiment, des oxydants, des activateurs de blanchiment, des catalyseurs de blanchiment, des photoactivateurs, des adoucissants pour le linge, des parfums, des arômes, des pigments, des enzymes, des vitamines, des produits pharmaceutiques, des antimicrobiens, des engrais, des explosifs, et des matériaux corrosifs. Le tamis moléculaire est de préférence du type mésoporeux et consiste principalement en un matériau cristallin, inorganique présentant après calcination un réseau de diffraction aux rayons X comportant au moins un pic à un espacement 'd' d'au moins 18Å. L'ingrédient actif est sorbé physiquement ou chimiquement dans les pores du tamis moléculaire.
PCT/US2000/004908 1999-02-27 2000-02-25 Procede de protection et/ou de liberation controlee d'ingredients actifs WO2000051724A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU37081/00A AU3708100A (en) 1999-02-27 2000-02-25 Method for protecting and/or controlled release of active ingredients

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GB9904485.1 1999-02-27

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10021165A1 (de) * 2000-04-29 2001-11-08 Henkel Kgaa System für die Freisetzung von Wirkstoffen
EP1358873A1 (fr) * 2002-04-30 2003-11-05 National Institute of Advanced Industrial Science and Technology Silice mésoporeuse ayant une fonction de controle permettant la mise en ou hors-service de la libération controllée de composés, méthode pour sa préparation et son utilisation
JP2004528328A (ja) * 2001-04-20 2004-09-16 スリーエム イノベイティブ プロパティズ カンパニー 徐放性粒子
US7083047B2 (en) 2002-10-03 2006-08-01 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Polymeric film for water soluble package
WO2009100995A2 (fr) 2008-02-13 2009-08-20 Evonik Degussa Gmbh Systèmes de produits stables au stockage pour des formulations de prémélange
US8597789B2 (en) 2009-08-05 2013-12-03 Evonik Degussa Gmbh Microstructured multifunctional inorganic coating additives for preventing fouling (growth of biofilm) in aquatic applications
CN104030802A (zh) * 2014-05-23 2014-09-10 北京市农林科学院 一种包膜控释肥及其制备方法
US9248319B2 (en) 2009-08-08 2016-02-02 Evonik Degussa Composite particles for use in oral hygiene
CN111888519A (zh) * 2020-08-13 2020-11-06 江西理工大学 一种含锶介孔生物玻璃-镁复合材料及其制备方法和应用

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD137599A1 (de) * 1978-07-19 1979-09-12 Detlef Kaufmann Mittel zur thermoregulierten freisetzung von parfuem im waschprozess
EP0240169A1 (fr) * 1986-03-15 1987-10-07 Fermenta Asc Europe Limited Préparation de compositions thérapeutiques pour applications vétérinaires
EP0336014A1 (fr) * 1988-04-08 1989-10-11 VECTORPHARMA INTERNATIONAL S.p.A. Compositions pharmaceutiques à effet retard, et une méthode pour leur préparation
US5015475A (en) * 1988-05-14 1991-05-14 Degesch Gmbh Method and means for preventing or delaying undesired phosphine levels
GB2249104A (en) * 1990-10-23 1992-04-29 Bp Chem Int Ltd Bleach activators
US5264203A (en) * 1990-01-25 1993-11-23 Mobil Oil Corporation Synthetic mesoporous crystalline materials
WO1994028107A1 (fr) * 1993-06-02 1994-12-08 The Procter & Gamble Company Systeme de diffusion de parfum comprenant des zeolites
WO1997029172A1 (fr) * 1996-02-09 1997-08-14 The Procter & Gamble Company Compositions pour le lavage de la vaisselle en machine comprenant des mesopores et des macropores siliceux
US5876690A (en) * 1997-02-11 1999-03-02 National Science Council Mesoporous aluminosilicate molecular sieves having "tubules-within-a-tubule" hierarchical order morphology and the preparation thereof
WO1999036357A1 (fr) * 1998-01-20 1999-07-22 Drexel University Matieres mesoporeuses et leurs procedes de fabrication

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD137599A1 (de) * 1978-07-19 1979-09-12 Detlef Kaufmann Mittel zur thermoregulierten freisetzung von parfuem im waschprozess
EP0240169A1 (fr) * 1986-03-15 1987-10-07 Fermenta Asc Europe Limited Préparation de compositions thérapeutiques pour applications vétérinaires
EP0336014A1 (fr) * 1988-04-08 1989-10-11 VECTORPHARMA INTERNATIONAL S.p.A. Compositions pharmaceutiques à effet retard, et une méthode pour leur préparation
US5015475A (en) * 1988-05-14 1991-05-14 Degesch Gmbh Method and means for preventing or delaying undesired phosphine levels
US5264203A (en) * 1990-01-25 1993-11-23 Mobil Oil Corporation Synthetic mesoporous crystalline materials
GB2249104A (en) * 1990-10-23 1992-04-29 Bp Chem Int Ltd Bleach activators
WO1994028107A1 (fr) * 1993-06-02 1994-12-08 The Procter & Gamble Company Systeme de diffusion de parfum comprenant des zeolites
WO1997029172A1 (fr) * 1996-02-09 1997-08-14 The Procter & Gamble Company Compositions pour le lavage de la vaisselle en machine comprenant des mesopores et des macropores siliceux
US5876690A (en) * 1997-02-11 1999-03-02 National Science Council Mesoporous aluminosilicate molecular sieves having "tubules-within-a-tubule" hierarchical order morphology and the preparation thereof
WO1999036357A1 (fr) * 1998-01-20 1999-07-22 Drexel University Matieres mesoporeuses et leurs procedes de fabrication

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10021165A1 (de) * 2000-04-29 2001-11-08 Henkel Kgaa System für die Freisetzung von Wirkstoffen
JP2004528328A (ja) * 2001-04-20 2004-09-16 スリーエム イノベイティブ プロパティズ カンパニー 徐放性粒子
EP1358873A1 (fr) * 2002-04-30 2003-11-05 National Institute of Advanced Industrial Science and Technology Silice mésoporeuse ayant une fonction de controle permettant la mise en ou hors-service de la libération controllée de composés, méthode pour sa préparation et son utilisation
US6902806B2 (en) 2002-04-30 2005-06-07 National Institute Of Advanced Science And Technology Mesoporous silica having controlled-release on-off control function, production method thereof and method using same
US7083047B2 (en) 2002-10-03 2006-08-01 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Polymeric film for water soluble package
DE102008000290A1 (de) 2008-02-13 2009-08-20 Evonik Degussa Gmbh Lagerstabile Produktsyteme für Prämixformulierungen
WO2009100995A2 (fr) 2008-02-13 2009-08-20 Evonik Degussa Gmbh Systèmes de produits stables au stockage pour des formulations de prémélange
US9199211B2 (en) 2008-02-13 2015-12-01 Evonik Degussa Gmbh Storage-stable product systems for premix formulations
US8597789B2 (en) 2009-08-05 2013-12-03 Evonik Degussa Gmbh Microstructured multifunctional inorganic coating additives for preventing fouling (growth of biofilm) in aquatic applications
US9248319B2 (en) 2009-08-08 2016-02-02 Evonik Degussa Composite particles for use in oral hygiene
CN104030802A (zh) * 2014-05-23 2014-09-10 北京市农林科学院 一种包膜控释肥及其制备方法
CN104030802B (zh) * 2014-05-23 2016-06-29 北京市农林科学院 一种包膜控释肥及其制备方法
CN111888519A (zh) * 2020-08-13 2020-11-06 江西理工大学 一种含锶介孔生物玻璃-镁复合材料及其制备方法和应用

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