CA2470376A1 - Uniform microcapsules - Google Patents
Uniform microcapsules Download PDFInfo
- Publication number
- CA2470376A1 CA2470376A1 CA002470376A CA2470376A CA2470376A1 CA 2470376 A1 CA2470376 A1 CA 2470376A1 CA 002470376 A CA002470376 A CA 002470376A CA 2470376 A CA2470376 A CA 2470376A CA 2470376 A1 CA2470376 A1 CA 2470376A1
- Authority
- CA
- Canada
- Prior art keywords
- core material
- process according
- microcapsules
- diacid
- membrane
- 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
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
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/20—After-treatment of capsule walls, e.g. hardening
- B01J13/206—Hardening; drying
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
- B01F23/40—Mixing liquids with liquids; Emulsifying
- B01F23/41—Emulsifying
- B01F23/4105—Methods of emulsifying
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F25/00—Flow mixers; Mixers for falling materials, e.g. solid particles
- B01F25/30—Injector mixers
- B01F25/31—Injector mixers in conduits or tubes through which the main component flows
- B01F25/314—Injector mixers in conduits or tubes through which the main component flows wherein additional components are introduced at the circumference of the conduit
- B01F25/3142—Injector mixers in conduits or tubes through which the main component flows wherein additional components are introduced at the circumference of the conduit the conduit having a plurality of openings in the axial direction or in the circumferential direction
- B01F25/31421—Injector mixers in conduits or tubes through which the main component flows wherein additional components are introduced at the circumference of the conduit the conduit having a plurality of openings in the axial direction or in the circumferential direction the conduit being porous
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
- Y10T428/2985—Solid-walled microcapsule from synthetic polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
- Y10T428/2985—Solid-walled microcapsule from synthetic polymer
- Y10T428/2987—Addition polymer from unsaturated monomers only
Abstract
The present invention teaches an improved process for preparing a population of microcapsules having a substantially uniform size distribution, especially useful for manufacture of carbonless paper. The improved process teaches use of membrane material having a pre-selected pore size in the capsule manufacture process. A core material is provided along with a receiving solution for receiving the core material. The receiving solution is a nonsolvent for the core material. The core material is passed under pressure through the membrane into a moving or turbulent receiving solution forming uniform droplets of core material dispersed in the receiving solution. Wall-forming material is added to the receiving solution for coating the core material droplets. The coating on the droplets is polymerized forming microcapsules. This novel process also lends itself to microcapsule formation in a continuous process.
Claims (31)
1. A process for preparing a population of microcapsules having a substantially uniform size distribution comprising:
providing a membrane having a selected pore size, providing a core material, providing a receiving solution for receiving the core material, the receiving solution being a nonsolvent for the core material, passing the core material under pressure through said membrane into the receiving solution to form uniform droplets of core material dispersed in the receiving solution, adding wall-forming material to the receiving solution for coating the core material droplets, polymerizing the coating on the core material droplets forming microcapsules.
providing a membrane having a selected pore size, providing a core material, providing a receiving solution for receiving the core material, the receiving solution being a nonsolvent for the core material, passing the core material under pressure through said membrane into the receiving solution to form uniform droplets of core material dispersed in the receiving solution, adding wall-forming material to the receiving solution for coating the core material droplets, polymerizing the coating on the core material droplets forming microcapsules.
2. The process according to claim 1 wherein the wall forming material is comprised of two reactive wall forming components, the first wall forming reactive component is dissolved in the core material, the second wall forming component is dissolved in the receiving solution.
3. The process according to claim 2 wherein the two reactive wall forming components comprise a diacid and a diol, a diester and a diol, a metal salt of dibasic acid and a dihalide, glycol ester and diacid, diacid chloride and diol, ethylene carbonate and diacid, anhydride and diol, diphenol and diacid, diacetate of diphenol and diacid, alkali metal salt of diphenol and a diacid halogen, a diamine and a dianhydride, a tetramine and a dianhydride.
4. The process according to claim 1 wherein the membrane is a porous inorganic or polymeric material.
5. The process according to claim 1 wherein the membrane is selected from glass, silicate, metal, metal silica compounds, metal silicate compounds, zeolites, alumina, titanic, silica, ceramic, graphite, powdered steel and polymeric beads.
6. The process according to claim 5 wherein the pore size of the membrane is from 0.25 to 20 microns.
7. The process according to claim 1 wherein the core material is a hydrophobic material and solvent for a chromogenic material.
8. The process according to claim 1 wherein the core material comprises a chromogen and a solvent selected from a dialkyl phathalate, alkyl biphenyl, alkyl benzene, diaryl ether, di(aralkyl)ether, aryl aralkyl ether, alkyl ketone, alkyl benzoate, aralkyl benzoate, alkylated naphthalene, a partially hydrogenated terphenyl, a vegetable oil, and a vegetable oil ester.
9. The process according to claim 1 wherein the core material is a hydrophillic material.
10. The process according to claim 1 wherein the transdermal pressure applied to the core material is at least 20 KPa.
11. The process according to claim 1 wherein the wall-forming material comprises a material comprises a material selected from a gellable colloid, carboxy methyl cellulose, gelatin, gelatin-gum arabic, melamine formaldehyde,. methylol melamine, urea formaldehyde, dimethylol urea, methylated dimethylol urea, methylated melamine formaldehyde, methylated methylol melamine, a gelatin-anionic polymer, alkylacrylate-acrylic acid copolymer, or reaction product with any of the foregoing.
12. The process according to claim 1 wherein the microcapsules have a broadness index of less than 1Ø
13. The process according to claim 1 wherein the microcapsules have a size distribution such that 80% of the population of microcapsules on a numerical basis are within two microns of the mean diameter.
14. The process according to claim 1 wherein the microcapsules have a size distribution such that 80% of the population of microcapsules on a numerical basis are within one micron of the mean diameter.
15. The process according to claim 1 wherein polymerizing the coating on the core material droplets to form microcapsules is accomplished by means of heating, pH
change or addition of a polymerization reactant.
change or addition of a polymerization reactant.
16. The microcapsules produced according to the process of claim 1.
17. A process for preparing a population of microcapsules having a substantially uniform size distribution useful for manufacture of carbonless paper comprising:
providing a membrane having a selected pore size, providing a hydrophobic core material, providing an aqueous solution for receiving the hydrophobic core material, passing the hydrophobic core material under pressure through said membrane into the aqueous solution to form uniform droplets of hydrophobic core material dispersed in the aqueous solution, adding wall-forming material to the aqueous solution to coat the core material droplets to form microcapsules, heating the microcapsules to polymerize the wall material, adjusting the pH to harden the wall material.
providing a membrane having a selected pore size, providing a hydrophobic core material, providing an aqueous solution for receiving the hydrophobic core material, passing the hydrophobic core material under pressure through said membrane into the aqueous solution to form uniform droplets of hydrophobic core material dispersed in the aqueous solution, adding wall-forming material to the aqueous solution to coat the core material droplets to form microcapsules, heating the microcapsules to polymerize the wall material, adjusting the pH to harden the wall material.
18. The process according to claim 17 wherein the wall forming material is comprised of two reactive wall forming components, the first wall forming reactive component is dissolved in the core material, the second wall forming component is dissolved in the receiving solution.
19. The process according to claim 18 wherein the two reactive wall forming components comprise a diacid and a diol, a diester and a diol, a metal salt of dibasic acid and a dihalide, glycol ester and diacid, diacid chloride and diol, ethylene carbonate and diacid, anhydride and diol, diphenol and diacid, diacetate of diphenol and diacid, alkali metal salt of diphenol and a diacid halogen, a diamine and a dianhydride, a tetramine and a dianhydride.
20. The process according to claim 17 wherein the membrane is a porous inorganic or polymeric material.
21. The process according to claim 17 wherein the membrane is selected from glass, silicate, metal, metal silica compounds, metal silicate compounds, zeolites, silica, ceramic, graphite, powdered steel and polymeric beads.
22. The process according to claim 17 wherein the pore size of the membrane is from 0.25 to 2.0 microns.
23. The process according to claim 17 wherein the core material is a hydrophobic material and solvent for a chromogenic material.
24. The process according to claim 17 wherein the core material comprises a chromogen and a solvent selected from a dialkyl phathalate, alkyl biphenyl, alkyl benzene, diaryl ether, di(aralkyl)ether, aryl aralkyl ether, alkyl ketone, alkyl benzoate, aralkyl benzoate, alkylated naphthalene, a partially hydrogenated terphenyl, a vegetable oil, and a vegetable oil ester.
25. The process according to claim 17 wherein the pressure applied to the core material is at least 20 KPa.
26. The process according to claim 17 wherein the wall-forming material comprises a material comprises a material selected from a gellable colloid, carboxy methyl cellulose, gelatin, gelatin-gum arabic, melamine formaldehyde, methylol melamine, urea formaldehyde, dimethylol urea, methylated dimethylol urea, methylated melamine formaldehyde, methylated methylol melamine, a gelatin-anionic polymer, alkylacrylate-acrylic acid copolymer, or reaction product with any of the foregoing.
27. The process according to claim 17 wherein the microcapsules have a broadness index of less than 1Ø
28. The process according to claim 17 wherein the microcapsules have a size distribution such that 80% of the population of microcapsules on a numerical basis are within two microns of the mean diameter.
29. The process according to claim 17 wherein the microcapsules have a size distribution such that 80% of the population of microcapsules on a numerical basis are within one micron of the mean diameter.
30. The microcapsules produced according to the process of claim 17.
31. A carbonless copy paper having a coating of microcapsules having a substantially uniform size distribution, said microcapsules produced by providing a membrane having a selected pore size, providing a hydrophobic core material comprising an oil and chromogenic material, providing an aqueous solution for receiving the hydrophobic core material, passing the hydrophobic core material under pressure through said membrane ' into the aqueous solution to form uniform droplets of hydrophobic core material dispersed in the aqueous solution adding wall-forming material to the aqueous solution to coat the core material droplets with a wall material, polymerizing the wall material to form microcapsules, then, coating the microcapsules onto a substrate.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/099,757 US6890592B2 (en) | 2002-03-13 | 2002-03-13 | Uniform microcapsules |
US10/099,757 | 2002-03-13 | ||
PCT/US2003/001801 WO2003078043A2 (en) | 2002-03-13 | 2003-01-22 | Uniform microcapsules |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2470376A1 true CA2470376A1 (en) | 2003-09-25 |
CA2470376C CA2470376C (en) | 2010-10-19 |
Family
ID=28039677
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2470376A Expired - Lifetime CA2470376C (en) | 2002-03-13 | 2003-01-22 | Uniform microcapsules |
Country Status (5)
Country | Link |
---|---|
US (2) | US6890592B2 (en) |
EP (1) | EP1490167B1 (en) |
JP (1) | JP2005519749A (en) |
CA (1) | CA2470376C (en) |
WO (1) | WO2003078043A2 (en) |
Families Citing this family (33)
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---|---|---|---|---|
WO2002020536A1 (en) * | 2000-09-08 | 2002-03-14 | San-Ei Gen F.F.I.,Inc. | Tetraphenylbacteriochlorin derivatives and compositions containing the same |
US7176159B1 (en) * | 2001-08-15 | 2007-02-13 | Iowa State University Research Foundation, Inc. | Catalyst and sorbent material for the production of hydrogen |
RU2339364C2 (en) * | 2003-04-29 | 2008-11-27 | Н.В.Органон, Nl | Method of solidification using anti-solvent |
US7531365B2 (en) * | 2004-01-08 | 2009-05-12 | International Flavors & Fragrances Inc. | Analysis of the headspace proximate a substrate surface containing fragrance-containing microcapsules |
FR2879476B1 (en) * | 2004-12-21 | 2007-04-20 | Univ Claude Bernard Lyon | NOVEL PROCESS FOR THE PREPARATION OF PARTICLES OF WHICH AT LEAST THE PERIPHERAL SURFACE IS OF A POLYMERIC NATURE, IMPLEMENTING A MEMBRANE REACTOR |
FR2885538B1 (en) * | 2005-05-16 | 2007-08-10 | Univ Claude Bernard Lyon | NOVEL PROCESS FOR PREPARING SOLID LIPID PARTICLES USING A MEMBRANE REACTOR |
US7327261B2 (en) * | 2005-07-27 | 2008-02-05 | Zih Corp. | Visual identification tag deactivation |
US7442439B2 (en) * | 2005-12-28 | 2008-10-28 | Kimberly-Clark Worldwide, Inc. | Microencapsulated heat delivery vehicles |
US7914891B2 (en) * | 2005-12-28 | 2011-03-29 | Kimberly-Clark Worldwide, Inc. | Wipes including microencapsulated delivery vehicles and phase change materials |
US20070145618A1 (en) * | 2005-12-28 | 2007-06-28 | Kimberly-Clark Worldwide, Inc. | Methods of making microencapsulated delivery vehicles |
US20070148446A1 (en) * | 2005-12-28 | 2007-06-28 | Kimberly-Clark Worldwide, Inc. | Wipes including microencapsulated delivery vehicles and processes of producing the same |
US20070148448A1 (en) * | 2005-12-28 | 2007-06-28 | Kimberly-Clark Worldwide, Inc. | Microencapsulated delivery vehicles including cooling agents |
US20070149435A1 (en) * | 2005-12-28 | 2007-06-28 | Kimberly-Clark Worldwide, Inc. | Cleansing composition including microencapsulated delivery vehicles |
US20070202185A1 (en) * | 2005-12-28 | 2007-08-30 | Kimberly-Clark Worldwide, Inc. | Microencapsulated Delivery Vehicles Having Fugitive Layers |
US20070145619A1 (en) * | 2005-12-28 | 2007-06-28 | Kimberly-Clark Worldwide, Inc. | Processes for producing microencapsulated delivery vehicles |
US7497351B2 (en) | 2006-05-30 | 2009-03-03 | Kimberly-Clark Worldwide, Inc. | Wet wipe dispensing system |
US7654412B2 (en) * | 2006-05-30 | 2010-02-02 | Kimberly-Clark Worldwide, Inc. | Wet wipe dispensing system for dispensing warm wet wipes |
US8167122B2 (en) * | 2006-06-12 | 2012-05-01 | C. En. Limited | Apparatus and cartridge for storage of compressed hydrogen gas |
US8192841B2 (en) * | 2006-12-14 | 2012-06-05 | Kimberly-Clark Worldwide, Inc. | Microencapsulated delivery vehicle having an aqueous core |
DE502007003920D1 (en) * | 2006-12-14 | 2010-07-08 | Sulzer Chemtech Ag | Porous dosing element with coating |
US20100272859A1 (en) * | 2007-08-28 | 2010-10-28 | Pepsico, Inc. | Delivery and controlled release of encapsulated water-insoluble flavorants |
US9186640B2 (en) * | 2007-08-28 | 2015-11-17 | Pepsico, Inc. | Delivery and controlled release of encapsulated lipophilic nutrients |
US20090233836A1 (en) * | 2008-03-11 | 2009-09-17 | The Procter & Gamble Company | Perfuming method and product |
US7924142B2 (en) | 2008-06-30 | 2011-04-12 | Kimberly-Clark Worldwide, Inc. | Patterned self-warming wipe substrates |
US8273435B2 (en) | 2009-06-01 | 2012-09-25 | Polymer Ventures, Inc. | Polyol coatings, articles, and methods |
FR2948581B1 (en) * | 2009-07-31 | 2011-09-09 | Centre Nat Rech Scient | HEART-ECORCE MATERIAL, METHOD FOR THE PREPARATION THEREOF AND USE FOR THE THERMOSTIMULATED DELIVERY OF SUSPENSIONS OF INTEREST |
CA2778251C (en) * | 2009-11-06 | 2015-12-22 | The Procter & Gamble Company | High efficiency capsules comprising benefit agent |
GB2494926B (en) * | 2011-09-26 | 2018-07-11 | Micropore Tech Ltd | Apparatus for particle production |
US9084963B2 (en) * | 2013-03-13 | 2015-07-21 | Triext, Llc | Microencapsulated immobilized liquid membrane for carbon dioxide capture and associated methods |
KR101907547B1 (en) * | 2016-12-13 | 2018-10-12 | 한국과학기술연구원 | Apparatus for fabricating capsule |
CA3073967A1 (en) * | 2018-01-23 | 2019-08-01 | Encapsys, Llc | Microencapsulated acidic materials |
CN108380146A (en) * | 2018-04-27 | 2018-08-10 | 江南大学 | A kind of preparation method and its ureaformaldehyde photochromic micro-encapsulation of ureaformaldehyde photochromic micro-encapsulation |
CN112691077B (en) * | 2020-12-30 | 2022-04-05 | 浙江康吉尔药业有限公司 | Processing method of glucose injection |
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CA2080424A1 (en) * | 1991-10-25 | 1993-04-26 | Jerry Moy | Microcapsules containing inorganic colloids and method for making the same |
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US5643506A (en) | 1995-02-03 | 1997-07-01 | The Mead Corporation | Continuous production of Emulsions and microcapsules of uniform particle size |
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US6143211A (en) | 1995-07-21 | 2000-11-07 | Brown University Foundation | Process for preparing microparticles through phase inversion phenomena |
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FR2747321B1 (en) | 1996-04-16 | 1998-07-10 | Centre Nat Rech Scient | PROCESS FOR THE PREPARATION OF AN EMULSION |
AU4202100A (en) * | 1999-04-06 | 2000-10-23 | E-Ink Corporation | Methods for producing droplets for use in capsule-based electrophoretic displays |
US6727203B2 (en) * | 2001-03-28 | 2004-04-27 | Fuji Photo Film Co., Ltd. | Method for producing microcapsules and heat-sensitive recording material |
-
2002
- 2002-03-13 US US10/099,757 patent/US6890592B2/en not_active Expired - Lifetime
-
2003
- 2003-01-22 WO PCT/US2003/001801 patent/WO2003078043A2/en active Application Filing
- 2003-01-22 JP JP2003576091A patent/JP2005519749A/en active Pending
- 2003-01-22 EP EP03736431.2A patent/EP1490167B1/en not_active Expired - Lifetime
- 2003-01-22 CA CA2470376A patent/CA2470376C/en not_active Expired - Lifetime
-
2005
- 2005-03-28 US US11/051,744 patent/US7122503B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US20030176282A1 (en) | 2003-09-18 |
EP1490167A2 (en) | 2004-12-29 |
WO2003078043A3 (en) | 2003-12-04 |
EP1490167B1 (en) | 2015-07-08 |
CA2470376C (en) | 2010-10-19 |
EP1490167A4 (en) | 2006-09-13 |
US6890592B2 (en) | 2005-05-10 |
US20050158547A1 (en) | 2005-07-21 |
JP2005519749A (en) | 2005-07-07 |
US7122503B2 (en) | 2006-10-17 |
WO2003078043A2 (en) | 2003-09-25 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKEX | Expiry |
Effective date: 20230123 |