CA2376593A1 - Method of particle formation - Google Patents

Method of particle formation Download PDF

Info

Publication number
CA2376593A1
CA2376593A1 CA002376593A CA2376593A CA2376593A1 CA 2376593 A1 CA2376593 A1 CA 2376593A1 CA 002376593 A CA002376593 A CA 002376593A CA 2376593 A CA2376593 A CA 2376593A CA 2376593 A1 CA2376593 A1 CA 2376593A1
Authority
CA
Canada
Prior art keywords
vehicle
suspension
fluid
solvent
vehicles
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.)
Granted
Application number
CA002376593A
Other languages
French (fr)
Other versions
CA2376593C (en
Inventor
Mazen Hermiz Hanna
Peter York
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.)
Nektar Therapeutics UK Ltd
Original Assignee
Bradford Particle Design Ltd.
Mazen Hermiz Hanna
Peter York
Bradford Particle Design Plc
Nektar Therapeutics Uk Ltd.
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 Bradford Particle Design Ltd., Mazen Hermiz Hanna, Peter York, Bradford Particle Design Plc, Nektar Therapeutics Uk Ltd. filed Critical Bradford Particle Design Ltd.
Publication of CA2376593A1 publication Critical patent/CA2376593A1/en
Application granted granted Critical
Publication of CA2376593C publication Critical patent/CA2376593C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • B01J2/00—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic
    • B01J2/02—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic by dividing the liquid material into drops, e.g. by spraying, and solidifying the drops
    • B01J2/04—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic by dividing the liquid material into drops, e.g. by spraying, and solidifying the drops in a gaseous medium
    • 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
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1682—Processes
    • A61K9/1688—Processes resulting in pure drug agglomerate optionally containing up to 5% of excipient
    • 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
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1682—Processes
    • A61K9/1694—Processes resulting in granules or microspheres of the matrix type containing more than 5% of excipient
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0403—Solvent extraction of solutions which are liquid with a supercritical fluid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0403—Solvent extraction of solutions which are liquid with a supercritical fluid
    • B01D11/0407—Solvent extraction of solutions which are liquid with a supercritical fluid the supercritical fluid acting as solvent for the solute
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0403—Solvent extraction of solutions which are liquid with a supercritical fluid
    • B01D11/0411—Solvent extraction of solutions which are liquid with a supercritical fluid the supercritical fluid acting as solvent for the solvent and as anti-solvent for the solute, e.g. formation of particles from solutions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0488—Flow sheets

Abstract

The invention provides a method for forming particles of a target substance, comprising (a) co-introducing into a particle formation vessel, under controlled temperature and pressure, a supercritical or near-critical anti-solvent fluid; a "target solution or suspension" of the target in a first vehicle; and a second vehicle which is soluble in the anti-solvent fluid; and (b) using the anti-solvent to disperse the target solution/suspension and the second vehicle, and to extract the vehicles, substantially simultaneously and substantially immediately on introduction of the fluids into the particle formation vessel, wherein the second vehicle is immiscible with the first, and wherein contact between the target solution/suspension and the second vehicle occurs a sufficiently short period of time before their dispersion by the anti-solvent, and with sufficient physical mixing, as to allow only insignificant, if any, phase separation to occur between the two vehicles between their contact with one another and their dispersion.

Claims (36)

1 A method for forming particles of a target substance, the method comprising (a) co-introducing into a particle formation vessel, the temperature and pressure in which are controlled, an anti-solvent fluid which is either a supercritical or a near-critical fluid; a solution or suspension of the target substance in a first vehicle (the "target solution/suspension"); and a second vehicle which is soluble or substantially soluble in the anti-solvent fluid;
and (b) using the anti-solvent fluid to disperse the target solution/suspension and the second vehicle, and to extract the vehicles, substantially simultaneously and substantially immediately on introduction of the fluids into the particle formation vessel, wherein the second vehicle is immiscible with the first vehicle, and wherein contact between the target solution/suspension and the second vehicle occurs a sufficiently short period of time before their dispersion by the anti-solvent fluid, and with sufficient physical mixing, as to allow only insignificant, if any, phase separation to occur between the two vehicles between their contact with one another and their dispersion.
2 A method according to claim 1, provided that the second vehicle is not a supercritical fluid.
3 A method according to claim 1 or claim 2, wherein contact between the target solution/suspension and the second vehicle occurs within a fluid inlet means used to introduce the fluids into the particle formation vessel, or at or immediately before the point of entry of the vehicles into the inlet means.
4 A method according to claim 3, wherein the contact occurs within the fluid inlet means.
A method according to claim 3 or claim 4, wherein the second vehicle is introduced into the inlet means separately from the target solution/suspension and the anti-solvent fluid, its direction of flow into the particle formation vessel being concurrent, and coaxial or substantially coaxial, with that of the target solution/suspension.
6 A method according to any one of claims 3 to 5, wherein the contact between the target solution/suspension and the second vehicle occurs either substantially simultaneously with, or immediately before, dispersion of the two vehicles by the anti-solvent fluid.
7 A method according to claim 6, wherein the contact occurs within about 0.001-10 seconds of the dispersion of the target solution/suspension and the second vehicle by the anti-solvent fluid.
8 A method according to claim 7, wherein the contact occurs within about 0.01-seconds of the dispersion.
9 A method according to any one of the preceding claims, wherein the first and second vehicles are immiscible in all or substantially all proportions.
A method according to claim 9, wherein the two vehicles are immiscible at first:second vehicle molar ratios lower than 20:80.
11 A method according to any one of the preceding claims, wherein the first vehicle is water and the second vehicle is a C4 or higher alcohol.
12 A method according to any one of claims 1 to 10, wherein the first vehicle is methanol and the second vehicle is a C5 or higher alkane.
13 A method according to any one of claims 1 to 10, wherein the first vehicle is ethylene glycol and the second vehicle is a haloalkane.
14 A method according to any one of the preceding claims, wherein the first and second vehicles are selected from the group consisting of water and 1-butanol;
water and ethyl acetate; methanol and n-pentane; methanol and n-octane;
methanol and hexane; methanol and cyclohexane; DMF (dimethyl formamide) and a higher alkane; DMSO (dimethyl sulphoxide) and a higher alkane; ethyl ether and DMSO; ethylene glycol and dichloromethane; ethylene glycol and 1,2-dichloroethane; glycerol and 3-pentanone; glycerol and ethyl acetate; 2-methoxyethanol and tetradecane; ethylformamide and hexane; 1-amino-2-propanol and isopropyl ether; 2-aminoethanol and dichloromethane; 2-aminoethanol and ethyl ether; 1,4-butanediol and butyl acetate; and water and dichloromethane.
15 A method according to any one of the preceding claims, wherein the relative amounts of the first and second vehicles used are such that, under the operating conditions used, the target solution/suspension and the second vehicle form a single phase mixture at the time of their contact with the anti-solvent fluid.
16 A method according to any one of the preceding claims, wherein there is an excess of the second vehicle over the first, at their point of contact with the anti-solvent fluid.
17 A method according to claim 16, wherein the molar ratio of the first to the second vehicle is less than 1:6.
18 A method according to any one of the preceding claims, wherein the target substance is for use in or as a pharmaceutical or pharmaceutical excipient.
19 A method according to any one of the preceding claims, wherein the target substance is a hydrophilic material.
20 A method according to claim 19, wherein the target substance is a sugar, protein or enzyme.
21 A method according to any one of the preceding claims, wherein two or more target substances are co-precipitated from the first and/or the second vehicle.
22 A method according to any one of the preceding claims, wherein the anti-solvent fluid is a supercritical fluid.
23 A method according to any one of the preceding claims, wherein each of the two vehicles comprises a single fluid material.
24 A method according to any one of the preceding claims, wherein the second vehicle is an anti-solvent for the target substance, and contains a crystallisation seed of a material which is insoluble in the second vehicle, to induce nucleation of the target substance when the second vehicle comes into contact with the target solution/suspension.
25 A method according to claim 24, wherein the crystallisation seed is a pharmaceutically acceptable carrier and the target substance is for use in or as a pharmaceutical.
26 A method according to claim 24, wherein the crystallisation seed comprises a pharmaceutically active material and the target substance comprises a material to be coated onto the pharmaceutically active material.
27 A method according to any one of the preceding claims, wherein the flow rate of the anti-solvent fluid is higher than those of the other fluids.
28 A method according to claim 27, wherein the ratio of the target solution/suspension flow rate to the anti-solvent flow rate, both measured at or immediately prior to the two fluids coming into contact with one another, is between 0.01 and 0.2.
29 A method according to any one of the preceding claims, wherein at the point of extraction of the two vehicles, into the anti-solvent fluid, they together constitute between 1 and 20 mole % of the fluid mixture then formed.
30 A method according to any one of the preceding claims, wherein the fluids are co-introduced into the particle formation vessel in a manner such that:

(a) the anti-solvent fluid and the target solution/suspension both enter the vessel at the same or substantially the same point, which is the same or substantially the same as the point at which they meet; and (b) the fluid inlet used to co-introduce the fluids is arranged so that the mechanical energy of the anti-solvent flow can facilitate intimate mixing of the fluids and also disperse them, and so that the anti-solvent can simultaneously extract the vehicles, at the point where the fluids meet.
31 A method according to claim 30, wherein the anti-solvent fluid and the target solution/suspension are co-introduced into the particle formation vessel with concurrent, and coaxial or substantially coaxial, directions of flow.
32 A method according to claim 30 or claim 31, wherein the fluid inlet comprises a nozzle having an outlet end communicating with the interior of the particle formation vessel, and two or more coaxial passages which terminate adjacent or substantially adjacent one another at the outlet end.
33 A method according to claim 32, wherein the nozzle has three coaxial passages, an inner, an intermediate and an outer.
34 A method according to claim 32 or claim 33, wherein the outlet of an inner nozzle passage is located slightly upstream, in use, of that of a surrounding passage, to allow a degree of internal mixing between fluids introduced through the two passages.
35 A method according to any one of the preceding claims, which additionally involves controlling one or more of (i) the flow rates of the anti-solvent fluid and/or the target solution/suspension and/or the second vehicle, (ii) the relative amounts of the two vehicles, (iii) the concentration of the target substance in the first vehicle, and (iv) the temperature and pressure inside the particle formation vessel, so as to influence the physicochemical characteristics of the particles formed.
36 A method for forming particles of a target substance, which is substantially as herein described with reference to the accompanying illustrative drawings.
CA002376593A 1999-07-07 2000-07-07 Method of particle formation Expired - Lifetime CA2376593C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB9915975.8A GB9915975D0 (en) 1999-07-07 1999-07-07 Method for the formation of particles
GB9915975.8 1999-07-07
PCT/GB2000/002606 WO2001003821A1 (en) 1999-07-07 2000-07-07 Method of particle formation

Publications (2)

Publication Number Publication Date
CA2376593A1 true CA2376593A1 (en) 2001-01-18
CA2376593C CA2376593C (en) 2009-12-01

Family

ID=10856857

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002376593A Expired - Lifetime CA2376593C (en) 1999-07-07 2000-07-07 Method of particle formation

Country Status (12)

Country Link
US (2) US6860907B1 (en)
EP (1) EP1191999B1 (en)
JP (1) JP4490016B2 (en)
AT (1) ATE235956T1 (en)
AU (1) AU773548B2 (en)
CA (1) CA2376593C (en)
DE (1) DE60001944T2 (en)
DK (1) DK1191999T3 (en)
ES (1) ES2195908T3 (en)
GB (2) GB9915975D0 (en)
MX (1) MXPA01013259A (en)
WO (1) WO2001003821A1 (en)

Families Citing this family (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9703673D0 (en) * 1997-02-21 1997-04-09 Bradford Particle Design Ltd Method and apparatus for the formation of particles
GB9810559D0 (en) * 1998-05-15 1998-07-15 Bradford Particle Design Ltd Method and apparatus for particle formation
GB9915975D0 (en) * 1999-07-07 1999-09-08 Bradford Particle Design Ltd Method for the formation of particles
GB9920558D0 (en) * 1999-08-31 1999-11-03 Bradford Particle Design Ltd Methods for particle formation and their products
GB9927011D0 (en) 1999-11-16 2000-01-12 Advanced Phytonics Ltd Method for the production of particles
FR2815540B1 (en) † 2000-10-19 2005-06-10 Separex Sa PROCESS FOR MANUFACTURING VERY FINE PARTICLES COMPRISING A PRINCIPLE INSERTED IN A HOST MOLECULE
GB0027357D0 (en) 2000-11-09 2000-12-27 Bradford Particle Design Plc Particle formation methods and their products
IL156618A0 (en) * 2000-12-28 2004-01-04 Altus Biologics Inc Crystals of whole antibodies and fragments thereof, methods for the preparation thereof and diagnostic kits utilizing the same
GB0102075D0 (en) 2001-01-26 2001-03-14 Astrazeneca Ab Process
BR0207570B1 (en) * 2001-02-26 2013-02-05 apparatus for forming micronized and submicronised particles of a substance, nozzle, and process performed using the apparatus.
CA2451185A1 (en) * 2001-06-21 2003-01-03 Altus Biologics, Inc. Spherical protein particles and methods of making and using them
EP1414633A4 (en) 2001-07-10 2005-01-26 Univ Technology Corp Devices and methods for the production of particles
GB0117696D0 (en) * 2001-07-20 2001-09-12 Bradford Particle Design Plc Particle information
GB0208742D0 (en) 2002-04-17 2002-05-29 Bradford Particle Design Ltd Particulate materials
ES2372032T3 (en) * 2001-10-22 2012-01-13 Dompé S.p.A. PROCESSING OF SUPERCRITICAL FLUIDS: PREPARATION OF PROTEIN MICROPARTICLES AND ITS STABILIZATION.
GB0126716D0 (en) * 2001-11-07 2002-01-02 Advanced Phytonics Ltd Method for the production of particles
US7582284B2 (en) * 2002-04-17 2009-09-01 Nektar Therapeutics Particulate materials
GB0216562D0 (en) * 2002-04-25 2002-08-28 Bradford Particle Design Ltd Particulate materials
US9339459B2 (en) 2003-04-24 2016-05-17 Nektar Therapeutics Particulate materials
GB0216780D0 (en) * 2002-07-19 2002-08-28 Bradford Particle Design Ltd Methods of particle formation
US20040202681A1 (en) * 2002-12-19 2004-10-14 Baxter International, Inc. Process for preparing pharmaceutical formulations using supercritical fluids
GB0229714D0 (en) * 2002-12-20 2003-01-29 Glaxo Group Ltd Novel apparatus and method
MXPA05007154A (en) * 2002-12-30 2005-09-21 Nektar Therapeutics Prefilming atomizer.
AU2004237131B2 (en) 2003-05-08 2009-09-10 Nektar Therapeutics Particulate materials
SE0303476D0 (en) 2003-12-22 2003-12-22 Censdelivery Ab Device, method and use for the formation of small particles
JP4545467B2 (en) * 2004-03-26 2010-09-15 株式会社大川原製作所 Supercritical fine particle production equipment
US7507823B2 (en) 2004-05-06 2009-03-24 Bristol-Myers Squibb Company Process of making aripiprazole particles
GB0418447D0 (en) * 2004-08-19 2004-09-22 Advanced Phytonics Ltd Process for preparing particles and apparatus
JP5016785B2 (en) * 2004-12-28 2012-09-05 株式会社奈良機械製作所 Fine particle generator
US20090053314A1 (en) * 2005-03-22 2009-02-26 Regeron, Inc. Submicronization of proteins using supercritical fluids
WO2007009164A1 (en) 2005-07-15 2007-01-25 Eiffel Technologies Limited Method of particle formation
EP2476412B1 (en) * 2006-10-11 2014-03-19 Crititech, Inc. Apparatus for precipitation of small medicament particles into use containers
GB0702402D0 (en) 2007-02-08 2007-03-21 Thar Pharmaceuticals Inc Method of creating crystalline substances
CN104188907A (en) * 2007-02-11 2014-12-10 Map药物公司 Method of therapeutic administration of DHE to enable rapid relief of migraine while minimizing side effect profile
US7827822B2 (en) * 2007-07-25 2010-11-09 Schott Corporation Method and apparatus for spray-forming melts of glass and glass-ceramic compositions
CA2706684C (en) * 2007-12-07 2016-01-12 Xspray Microparticles Ab Method and arrangement for the production of particles
WO2010151804A1 (en) * 2009-06-26 2010-12-29 Map Pharmaceuticals, Inc. Administration of dihydroergotamine mesylate particles using a metered dose inhaler
GB201016433D0 (en) * 2010-09-30 2010-11-17 Q Chip Ltd Apparatus and method for making solid beads
GB201016436D0 (en) 2010-09-30 2010-11-17 Q Chip Ltd Method of making solid beads
MX350838B (en) 2011-02-11 2017-09-18 Grain Proc Corporation * Salt composition.
US9925512B2 (en) 2013-03-14 2018-03-27 Crititech, Inc. Equipment assembly for and method of processing particles
US8778181B1 (en) 2013-03-14 2014-07-15 Crititech, Inc. Equipment assembly for and method of processing particles
US20170050337A1 (en) * 2013-05-02 2017-02-23 Melior Innovations, Inc. Formation apparatus, systems and methods for manufacturing polymer derived ceramic structures
GB201402556D0 (en) 2014-02-13 2014-04-02 Crystec Ltd Improvements relating to inhalable particles
US10252270B2 (en) * 2014-09-08 2019-04-09 Arizona Board Of Regents On Behalf Of Arizona State University Nozzle apparatus and methods for use thereof
US10806770B2 (en) 2014-10-31 2020-10-20 Monash University Powder formulation
DE102015007604A1 (en) * 2015-06-12 2016-12-29 Messer France S.A.S Apparatus and method for cooling and atomising liquid or pasty substances
WO2017013498A2 (en) 2015-07-22 2017-01-26 Anavex Life Sciences Corp. Crystal forms of tetra-hydro-n, n-dimethyl-2, 2-diphenyl-3-furanmethanamine hydrochloride, processes for making such forms, and their pharmaceutical compositions
CN108969555B (en) * 2017-09-25 2021-08-10 安徽九鑫药业有限公司 A Chinese medicinal composition comprising herba Epimedii with kidney invigorating, blood and essence replenishing, and immunity improving effects, and its preparation method
US11724241B2 (en) 2018-02-15 2023-08-15 Cambridge Enterprise Limited Constant shear continuous reactor device
CN112657301A (en) * 2020-12-01 2021-04-16 大连理工大学 Supercritical gas-solid separation device and method
EP4190437A1 (en) * 2021-12-03 2023-06-07 SiTec PharmaBio SL Process and apparatus for the manufacture of solid microparticles

Family Cites Families (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1078283B (en) 1958-06-12 1960-03-24 Bayer Ag Process for enveloping or embedding active pharmaceutical ingredients
US4361285A (en) 1980-06-03 1982-11-30 Fluid Kinetics, Inc. Mixing nozzle
US4328107A (en) 1980-11-28 1982-05-04 Synergo, Inc. Process and apparatus for forming dispersions
US4582731A (en) 1983-09-01 1986-04-15 Battelle Memorial Institute Supercritical fluid molecular spray film deposition and powder formation
US4702799A (en) 1985-09-03 1987-10-27 Nestec S.A. Dryer and drying method
US4737384A (en) 1985-11-01 1988-04-12 Allied Corporation Deposition of thin films using supercritical fluids
DE3787533T2 (en) 1987-12-21 1994-01-20 Union Carbide Corp Use of supercritical liquids as a thinner when spraying coatings.
DE3744329A1 (en) 1987-12-28 1989-07-06 Schwarz Pharma Gmbh METHOD FOR THE PRODUCTION OF AT LEAST ONE ACTIVE AGENT AND A TRAITER COMPRISING PREPARATION
JPH01176437A (en) 1987-12-29 1989-07-12 Ono Pharmaceut Co Ltd Method for rendering organic substance into fine particles
US4919853A (en) 1988-01-21 1990-04-24 The United States Of America As Represented By The United States Department Of Energy Apparatus and method for spraying liquid materials
US4977785A (en) 1988-02-19 1990-12-18 Extrel Corporation Method and apparatus for introduction of fluid streams into mass spectrometers and other gas phase detectors
US5707634A (en) 1988-10-05 1998-01-13 Pharmacia & Upjohn Company Finely divided solid crystalline powders via precipitation into an anti-solvent
DE68907062T2 (en) 1988-10-05 1993-10-07 Upjohn Co FINE DISTRIBUTED SOLID CRYSTALLINE POWDER BY DEPOSIT IN AN ANTI-SOLVENT.
US5009367A (en) 1989-03-22 1991-04-23 Union Carbide Chemicals And Plastics Technology Corporation Methods and apparatus for obtaining wider sprays when spraying liquids by airless techniques
US5106659A (en) 1989-10-04 1992-04-21 Nordson Corporation Method and apparatus for spraying a liquid coating containing supercritical fluid or liquified gas
US4970093A (en) 1990-04-12 1990-11-13 University Of Colorado Foundation Chemical deposition methods using supercritical fluid solutions
US5264536A (en) * 1990-12-06 1993-11-23 Exxon Research And Engineering Company Supercritical mixed-solvent separation of polymer mixtures
DE4118230A1 (en) 1990-12-20 1992-06-25 Bayer Ag METHOD OF ISOLATING POLYMERS FROM THEIR SOLVENTS WITH CARBON DIOXIDE-CONTAINING LIQUIDS
DE4041563A1 (en) 1990-12-22 1992-06-25 Sanol Arznei Schwarz Gmbh METHOD FOR PRODUCING ACTIVE MICROPARTICLES FROM HYDROLYTICALLY DEGRADABLE POLYMERS
DE4117751A1 (en) 1991-05-30 1992-12-03 Bayer Ag METHOD FOR INSULATING POLYCARBONATES
JPH0557166A (en) 1991-08-31 1993-03-09 Kobe Steel Ltd Production of coated fine particle
US6063910A (en) 1991-11-14 2000-05-16 The Trustees Of Princeton University Preparation of protein microparticles by supercritical fluid precipitation
US5639441A (en) 1992-03-06 1997-06-17 Board Of Regents Of University Of Colorado Methods for fine particle formation
AU5171293A (en) 1992-10-14 1994-05-09 Regents Of The University Of Colorado, The Ion-pairing of drugs for improved efficacy and delivery
AU678788B2 (en) 1992-11-02 1997-06-12 Ferro Corporation Method of preparing coating materials
EP0612697B1 (en) 1993-02-24 1998-01-21 Sulzer Chemtech AG Purification of salt containing waste water by wet oxidation at supercritical conditions
US5554382A (en) 1993-05-28 1996-09-10 Aphios Corporation Methods and apparatus for making liposomes
GB9313650D0 (en) * 1993-07-01 1993-08-18 Glaxo Group Ltd Method and apparatus for the formation of particles
GB9313642D0 (en) * 1993-07-01 1993-08-18 Glaxo Group Ltd Method and apparatus for the formation of particles
SI9400079B (en) 1994-02-15 2003-02-28 Dr. Weidner Eckhard, Dipl. Ing. Method and device for extraction and fractionation of small particles from solutions saturated with gas
GB9413202D0 (en) * 1994-06-30 1994-08-24 Univ Bradford Method and apparatus for the formation of particles
US5716558A (en) 1994-11-14 1998-02-10 Union Carbide Chemicals & Plastics Technology Corporation Method for producing coating powders catalysts and drier water-borne coatings by spraying compositions with compressed fluids
MX9504934A (en) 1994-12-12 1997-01-31 Morton Int Inc Smooth thin film powder coatings.
US5833891A (en) * 1996-10-09 1998-11-10 The University Of Kansas Methods for a particle precipitation and coating using near-critical and supercritical antisolvents
EP0885038B1 (en) * 1996-03-01 2011-06-15 The University Of Kansas Methods and apparatus for particle precipitation and coating using near-critical and supercritical antisolvents
GB9703673D0 (en) 1997-02-21 1997-04-09 Bradford Particle Design Ltd Method and apparatus for the formation of particles
GB9804379D0 (en) * 1998-03-02 1998-04-22 Bradford Particle Design Ltd Method of particle formation
GB9810559D0 (en) 1998-05-15 1998-07-15 Bradford Particle Design Ltd Method and apparatus for particle formation
GB9915975D0 (en) * 1999-07-07 1999-09-08 Bradford Particle Design Ltd Method for the formation of particles

Also Published As

Publication number Publication date
WO2001003821A1 (en) 2001-01-18
DE60001944D1 (en) 2003-05-08
US7150766B2 (en) 2006-12-19
DE60001944T2 (en) 2003-12-24
GB2354968A (en) 2001-04-11
US6860907B1 (en) 2005-03-01
CA2376593C (en) 2009-12-01
ES2195908T3 (en) 2003-12-16
AU5699000A (en) 2001-01-30
US20050206023A1 (en) 2005-09-22
JP2003504178A (en) 2003-02-04
JP4490016B2 (en) 2010-06-23
EP1191999B1 (en) 2003-04-02
AU773548B2 (en) 2004-05-27
GB0016618D0 (en) 2000-08-23
MXPA01013259A (en) 2002-12-13
ATE235956T1 (en) 2003-04-15
EP1191999A1 (en) 2002-04-03
GB2354968B (en) 2001-09-12
DK1191999T3 (en) 2003-07-21
GB9915975D0 (en) 1999-09-08

Similar Documents

Publication Publication Date Title
CA2376593A1 (en) Method of particle formation
JP2003504178A5 (en)
EP0767702B1 (en) Method and apparatus for the formation of particles
AU2002236021B2 (en) Apparatus and method for micron and submicron particle formation
FI67788C (en) FARING PROCESSING FOR SPRING TEMPERATURE FUMPER PRODUCTS
EP0706507B1 (en) Salmeterol xinafoate with controlled particle size
AU3720999A (en) Methods and apparatus for particle formation
EP1440082B1 (en) Supercritical fluids processing: preparation of protein microparticles and their stabilisation
KR100600691B1 (en) Incorporation of Active Substances in Carrier Matrixes
US8585942B2 (en) Process and arrangement for producing particles utilizing subcritical fluids
CA2288526A1 (en) Seamless capsule for synthesizing biopolymer and method for producing the same
JPWO2004026457A1 (en) Method for producing microcapsules

Legal Events

Date Code Title Description
EEER Examination request
MKEX Expiry

Effective date: 20200707