CA2470376A1 - Uniform microcapsules - Google Patents

Uniform microcapsules Download PDF

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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
Application number
CA002470376A
Other languages
French (fr)
Other versions
CA2470376C (en
Inventor
Troy Ronald Seehafer
George Arthur Stahler
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.)
Appvion Operations Inc
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2470376A1 publication Critical patent/CA2470376A1/en
Application granted granted Critical
Publication of CA2470376C publication Critical patent/CA2470376C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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.
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.
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.
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.
CA2470376A 2002-03-13 2003-01-22 Uniform microcapsules Expired - Lifetime CA2470376C (en)

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

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Family Applications (1)

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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)

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Also Published As

Publication number Publication date
EP1490167B1 (en) 2015-07-08
CA2470376C (en) 2010-10-19
WO2003078043A3 (en) 2003-12-04
US20050158547A1 (en) 2005-07-21
US20030176282A1 (en) 2003-09-18
EP1490167A2 (en) 2004-12-29
WO2003078043A2 (en) 2003-09-25
US7122503B2 (en) 2006-10-17
EP1490167A4 (en) 2006-09-13
US6890592B2 (en) 2005-05-10
JP2005519749A (en) 2005-07-07

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