USH1839H - Supercritical fluid processes - Google Patents
Supercritical fluid processes Download PDFInfo
- Publication number
- USH1839H USH1839H US08/839,273 US83927397A USH1839H US H1839 H USH1839 H US H1839H US 83927397 A US83927397 A US 83927397A US H1839 H USH1839 H US H1839H
- Authority
- US
- United States
- Prior art keywords
- wax
- accordance
- vessel
- solution
- particles
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 83
- 230000008569 process Effects 0.000 title claims abstract description 81
- 239000012530 fluid Substances 0.000 title claims description 9
- 239000002245 particle Substances 0.000 claims abstract description 41
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 239000000654 additive Substances 0.000 claims abstract description 7
- 230000000996 additive effect Effects 0.000 claims abstract description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 48
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 39
- -1 polypropylene Polymers 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 25
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 20
- 239000001569 carbon dioxide Substances 0.000 claims description 19
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 17
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 16
- 239000004743 Polypropylene Substances 0.000 claims description 15
- 229920001155 polypropylene Polymers 0.000 claims description 15
- 239000004698 Polyethylene Substances 0.000 claims description 11
- 229920000573 polyethylene Polymers 0.000 claims description 11
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 10
- 239000001294 propane Substances 0.000 claims description 10
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 8
- 239000001273 butane Substances 0.000 claims description 8
- 239000001282 iso-butane Substances 0.000 claims description 8
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 8
- 230000001376 precipitating effect Effects 0.000 claims description 6
- 238000011068 loading method Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims description 2
- 230000000717 retained effect Effects 0.000 claims description 2
- 238000007789 sealing Methods 0.000 claims description 2
- 239000001993 wax Substances 0.000 description 48
- 239000000463 material Substances 0.000 description 13
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000007788 liquid Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229920002313 fluoropolymer Polymers 0.000 description 3
- 239000004811 fluoropolymer Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
- 239000006193 liquid solution Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910008334 ZrO(NO3)2 Inorganic materials 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000002356 laser light scattering Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C08J3/14—Powdering or granulating by precipitation from solutions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2391/00—Characterised by the use of oils, fats or waxes; Derivatives thereof
- C08J2391/06—Waxes
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Definitions
- This invention is generally directed to processes, and more specifically, the present invention relates to processes for the preparation of small, and submicron particles, for example wherein small is from about 0.001 to about 4 microns, or submicron of from about 0.05 to about 1.0 micron in average particle diameter, wherein undesirable solvents can be avoided, and wherein a supercritical fluid or compressed liquid, such as carbon dioxide, ethane, propane, butane, isobutane, pentane, chlorodifluoromethane or trifluoromethane is selected as the solvent.
- the present invention in embodiments relates to a process for the preparation of submicron particles, such as toner wax particles, which comprises the micronization and spraying of these particles from a supercritical solution.
- the particles obtained can be selected as additives for toners of resin and pigment, and wherein the toners can be selected for xerographic imaging and printing processes, including digital processes.
- the waxes are known, for example 660P available from Sanyo Chemicals of Japan.
- RESS Rapid Expansion of a Supercritical Solution
- PCA compressed antisolvent
- RESS Rapid Expansion of a Supercritical Solution
- PCA compressed antisolvent
- RESS Rapid Expansion of a Supercritical Solution
- PCA compressed antisolvent
- RESS Rapid Expansion of a Supercritical Solution
- RESS can be selected for the preparation of fibers of polystyrene, poly(methyl methacrylate) , and certain fluoropolymers.
- Matson et al. Ind. Eng. Chem. Res. 1987, 26, 2298), there is illustrated the use of RESS for several metal oxides including SiO 2 , GeO 2 -H 2 O and ZrO(NO 3 ) 2 -ethanol.
- supercritical water was necessary at temperatures ranging from about 350° C. to about 475° C.
- Matson et al. also demonstrates that SCF pentane can be selected for the preparation of polystyrene spheres and fibers.
- Mawson et al. (Macromolecules, 1995, 28, 3182) demonstrates similar process viability for RESS in producing spherical and certain fluoropolymer particles from SCF carbon dioxide. Few polymers are soluble in carbon dioxide, and are, therefore, not suitable for RESS in carbon dioxide. However, many fluoropolymers, including, poly(1,1,2,2-tetrahydroperfluorodecylacrylate), and silicones exhibit substantive solubility.
- U.S. Pat. No. 4,734,227 illustrates RESS to provide micronized polyimide material for thin powder coatings. Additionally, the use of a secondary supercritical solvent allows for the production of long thin fibers of nylons or polyesters.
- U.S. Pat. No. 4,970,093 describes a process in which RESS is used to produce an aerosol such that a reaction between the precipitated material and the expanding solvent transpires to form a surface adhering film.
- An additional difficulty is that, unless the material to be granulated can be fed to the vessel continuously under pressure, the solution conditions change as the expansion across the nozzle depletes the material inside. If the process is operated at a constant pressure mode via the continuous addition of solvent, the mole fraction of the material being granulated diminishes and a broader size dispersity of the precipitating material results. When the process is operated in a batch mode without any addition, the pressure decreases as material exits the reactor. This change in pressure can cause premature precipitation of the material being granulated inside the vessel, and the orifice can plug as a result.
- the material being granulated is dissolved in a pressurized liquid solution with negligible solubility in the vapor phase, and if it is this liquid phase being fed to the housing containing the RESS expansion nozzle, then a constant mole fraction solution can be processed and a narrower size dispersity of the precipitated product can be realized. Additionally, the energy savings of heating the expansion nozzle alone to above the critical temperature and not the entire vessel can be substantial.
- Particulate materials are of importance for xerographic inks, and dry toner particles comprised of resin, pigment, charge control additive, external surface additives and sometimes a polymeric wax.
- Wax addition is needed primarily to ensure the release of the fused toner image from the surface of the fuser roll.
- Fusing is the final step of the xerographic process and involves intimate contact between the fuser and the toner residing as a latent image on the paper's surface. The heat of the fuser and the shear imparted to the toner by the fuser causes the latent image of the toner to fuse to the paper.
- One difficulty with this process that arises is adhesion of the toner to the fuser and not the paper, a phenomenon known as hot offset.
- the dispersion of wax inside a toner particle facilitates the release of toner from the fuser.
- both shear forces and temperature gradients are imparted to the toner.
- the dispersed wax being interfacially active, flows to reside preferentially between the surface of the toner and fuser. As the surface energy of wax is lower than the toner resin, release of the toner from the fuser is facilitated and hot offset is mitigated.
- waxes are not thermodynamically miscible with toner resins. Therefore, the dispersion of wax is not uniform throughout an individual toner particle, nor is the weight fraction of wax in the toner uniformly distributed among the toner particles. Therefore, a greater propensity exists for hot offset amongst the particles that contain little or no wax.
- compatibilizers are often used.
- Typical compatibilizers are block or graft copolymers, and their primary function is to promote the thermodynamic miscibility of wax domains in the toner resin and thereby ensure the uniform distribution and function of wax with the toner particles.
- compatibilizer One drawback to the use of compatibilizer, however, is that the propensity of the wax to flow to the interfacial area is reduced.
- the utility of the wax in toner is diminished as compatibilizer, by promoting miscibility, inhibits its flow to the interfacial region during fusing.
- Another object of the present invention resides in the provision of simple processes for the preparation of submicron toner additives.
- the present invention relates to the provision of processes for the preparation of small, or submicron wax particles utilizing supercritical or compressed liquid carbon dioxide, ethane, propane, trifluoromethane, and the like as the solvent.
- Embodiments of the present invention include a process for the preparation of small size wax particles, which comprises the micronization of the particles from a supercritical solvent, and the particles generated are comprised of a wax; wherein the wax is, for example, polypropylene, or polyethylene; wherein the micronization is accomplished by spraying the particles with the supercritical solvent through an orifice; wherein subsequent to the micronization the particles are isolated and are of a size diameter of from about 0.001 to about 4, or from about 0.001 to about 1.0 micron in volume average diameter; and wherein the process is accomplished, for example, at a pressure of from about 600 to about 5,000 pounds per square inch and at a temperature of from about 30° C. to about 200° C. (Centigrade).
- the process in embodiments is initiated with a loading of the polypropylene or polyethylene toner wax into a high pressure vessel in an amount ranging from 0.001 to about 50 weight/volume percent, or from about 0.001 to about 50 grams per 100 milliliters of reactor volume.
- the vessel is subsequently sealed.
- the vessel is then heated to the desired temperature, ranging, for example, from about 30° C. to about 500° C., with preferred temperatures being from about 50° C. to about 150° C.
- the fluid solvent for example CO 2 , C 2 H 6 , C 3 H 8 , CHCIF 2 , C 4 H 10 , iso-C 4 H 10 , C 5 H 12 or CHF 3 , is then added to the vessel to yield a solution density ranging from about 0.5 to about 2.5 grams/milliliter. Pressures generated can range from about 30 bar to about 800 bar.
- the wax/material to be precipitated After the wax/material to be precipitated has dissolved, it is applied to the expansion chamber sufficient to maintain the temperature at or above the critical temperature of the solution being fed, for example from about 30° C. to about 500° C.
- a valve from the source of the solvent that is at a higher, for example from about 35 to about 805 bar, pressure than the vessel pressure is then opened to initiate fluid flow through the precipitation orifice.
- a valve V1 to the vessel is opened and valve V2 is subsequently closed.
- This pressurization of the expansion chamber prior to flow from the pressure vessel is selected primarily to prevent precipitation of wax upstream of the expansion nozzle and subsequent plugging of the orifice.
- the precipitated wax product is then collected via a downstream filtration device.
- Embodiments of the present invention include: A process for the preparation of toner additive wax particles, which comprises the micronization of the wax particles from a supercritical solution; a process wherein the wax particles obtained are from about 0.001 to about 4 microns in volume average diameter; a process wherein the wax particles are inserted into and sealed in a high pressure vessel at a loading of from about 0.001 to about 50 weight/volume percent, or from about 0.001 to about 50 grams per 100 milliliters of vessel volume; the vessel is subsequently heated to from about 30° C. to about 400° C.
- the vessel is then agitated; the resulting solution is subsequently expanded across an orifice of, for example, from 5 to 100 microns in diameter, and which orifice has been heated to a temperature higher than the critical temperature of the solution, and which temperature is, for example, from about 50° C.
- the resulting precipitating wax is separated from the expanding gas stream; a process wherein the supercritical fluid is carbon dioxide; a process wherein the supercritical solution, or solvent is carbon dioxide, ethane, propane, butane, isobutane, pentane, chlorodifluoromethane or trifluoromethane; a process wherein the wax is polypropylene, or polyethylene; a process wherein the wax is polypropylene, or polyethylene, each with a M w of from about 500 to about 20,000 Dalton and an M n of from about 250 to about 10,000 Dalton; a process wherein the micronization is accomplished by rapid expansion of the supercritical solution, thereby generating the wax particles from the supercritical solution; a process wherein, subsequent to the micronization, the particles are isolated and are of a small size of from about 0.001 to about 4.0 microns in volume average diameter; a process wherein the process is accomplished at a pressure of from about 40 bar to about 850
- the supercritical solution is comprised of a carbon dioxide fluid and which carbon dioxide is at a temperature of above about 31° C. and a pressure of about 71 bar to 232 bar; a process wherein there is formed a supercritical phase at above the critical temperature of about 31° C.
- a process wherein the polypropylene is of a low molecular weight with an M w of from about 1,000 to about 25,000 and an M n of from about 500 to about 12,000; a process wherein the polyethylene is of a low molecular weight with an M w of from about 1,000 to about 25,000 and an M n of from about 500 to about 12,000; a process wherein the polypropylene is of a low molecular weight of from about 500 to about 10,000 number average; and wherein the polyethylene is of a low molecular weight of from about 700 to about 2,000 number average; a process for the preparation of wax with a small diameter size, which process comprises inserting and sealing the wax in a high pressure vessel at a loading of from 0.001 to 50 weight/volume percent, or from about 0.001 to about 50 grams per 100 milliliters of vessel volume, the vessel being subsequently heated to from about 30°C.
- the vessel contains a solvent of carbon dioxide, ethane, propane, butane, isobutane, pentane, chlorodifluoromethane or trifluoromethane, sufficient to yield an average density of from 0.7 to 1.5 grams/cc in the vessel; the vessel is then agitated for from about 1 to about 60 minutes to dissolve the wax; the solution from the lower or liquid phase of the vessel is then expanded across an orifice in the expansion chamber of from 5 to 100 microns in diameter, and which chamber is retained at a temperature above the critical temperature of the solution, which temperature is from about 40° C.
- Heating is then applied to an RESS expansion nozzle (30 ⁇ m diameter) to bring it and the entire expansion chamber to 400° C.
- a high pressure source of pure pentane (from, for example, a high pressure liquid pump operating at, for example, 60 bar) is directed into the expansion chamber.
- a high pressure source of pure pentane from, for example, a high pressure liquid pump operating at, for example, 60 bar
- the valve to the reactor is opened, followed by the closing of the valve to the pentane solvent source.
- the precipitating polypropylene is separated from the stream of pentane vapor by a downstream filtration device.
- the particle size of from 0.01 to 5.0 microns, and the particle size distribution of from 1.0 to 9.0 of the precipitated polypropylene can be measured with a known laser light scattering technique.
- Example I The process of Example I is repeated with the exception that there is selected as the solvent propane instead of pentane, and it is believed that substantially similar results are obtainable.
- Example I The process of Example I is repeated with the exception that there is selected as the solvent isobutane instead of pentane, and it is believed that substantially similar results are obtainable.
- Example I The process of Example I is repeated with the exception that there is selected as the solvent butane instead of pentane, and it is believed that substantially similar results are obtainable.
- Example I The process of Example I is repeated with the exception that there is selected as the solvent supercritical fluid carbon dioxide instead of pentane, and it is believed that substantially similar results are obtainable.
- Example I The process of Example I is repeated with the exception that there is selected as the solvent chlorodifluoromethane instead of pentane, and it is believed that substantially similar results are obtainable.
- Example I The process of Example I is repeated with the exception that there is selected as the solvent ethane instead of pentane, and it is believed that substantially similar results are obtainable.
- Example I The process of Example I is repeated with the exception that there is selected as the solvent ethane instead of pentane, and it is believed that substantially similar results are obtainable.
- Example I The process of Example I is repeated with the exception that there is selected polyethylene instead of polypropylene, and it is believed that substantially similar results are obtainable.
- Example I The process of Example I is repeated with the exception that there is selected propane at 150° C. instead of pentane at 300° C.
- the expansion chamber is also at 200° C., not 400°C. as in Example I. It is believed that substantially similar results would be obtainable.
Abstract
Description
Claims (21)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/839,273 USH1839H (en) | 1997-04-17 | 1997-04-17 | Supercritical fluid processes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/839,273 USH1839H (en) | 1997-04-17 | 1997-04-17 | Supercritical fluid processes |
Publications (1)
Publication Number | Publication Date |
---|---|
USH1839H true USH1839H (en) | 2000-02-01 |
Family
ID=25279297
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/839,273 Abandoned USH1839H (en) | 1997-04-17 | 1997-04-17 | Supercritical fluid processes |
Country Status (1)
Country | Link |
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US (1) | USH1839H (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6132653A (en) * | 1995-08-04 | 2000-10-17 | Microcoating Technologies | Chemical vapor deposition and powder formation using thermal spray with near supercritical and supercritical fluid solutions |
US20030054957A1 (en) * | 2001-07-12 | 2003-03-20 | Irvin Glen C. | Surfactant assisted nanomaterial generation process |
US20060029676A1 (en) * | 2004-08-03 | 2006-02-09 | Clemson University | Aqueous suspension of nanoscale drug particles from supercritical fluid processing |
US20060275542A1 (en) * | 2005-06-02 | 2006-12-07 | Eastman Kodak Company | Deposition of uniform layer of desired material |
WO2008006691A1 (en) * | 2006-07-13 | 2008-01-17 | Unilever N.V. | Surface-active material and its applications |
US20110236818A1 (en) * | 2010-03-25 | 2011-09-29 | Masahide Yamada | Method for preparing particulate release agent, toner using the particulate release agent, and method for preparing the toner |
US20160143134A1 (en) * | 2014-11-17 | 2016-05-19 | Ibiden Co., Ltd. | Wiring board with built-in metal block and method for manufacturing the same |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4734451A (en) * | 1983-09-01 | 1988-03-29 | Battelle Memorial Institute | Supercritical fluid molecular spray thin films and fine powders |
US5312882A (en) * | 1993-07-30 | 1994-05-17 | The University Of North Carolina At Chapel Hill | Heterogeneous polymerization in carbon dioxide |
-
1997
- 1997-04-17 US US08/839,273 patent/USH1839H/en not_active Abandoned
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4734451A (en) * | 1983-09-01 | 1988-03-29 | Battelle Memorial Institute | Supercritical fluid molecular spray thin films and fine powders |
US5312882A (en) * | 1993-07-30 | 1994-05-17 | The University Of North Carolina At Chapel Hill | Heterogeneous polymerization in carbon dioxide |
US5382623A (en) * | 1993-07-30 | 1995-01-17 | The University Of North Carolina At Chapel Hill | Heterogeneous polymerization in carbon dioxide |
US5451633A (en) * | 1993-07-30 | 1995-09-19 | The University Of North Carolina At Chapel Hill | Heterogeneous polymerization in carbon dioxide |
US5506317A (en) * | 1993-07-30 | 1996-04-09 | The University Of North Carolina At Chapel Hill | Heterogeneous polymerization in carbon dioxide |
Non-Patent Citations (6)
Title |
---|
CAPLUS Abstract 1997:517308 of dissertation by Gregory Griscik entitled "Wax Particle Formation from . . . Supercritical Solutions," Georgia Inst. of Tech., Atlanta, GA, USA, 1996. |
CAPLUS Abstract 1997:517308 of dissertation by Gregory Griscik entitled Wax Particle Formation from . . . Supercritical Solutions, Georgia Inst. of Tech., Atlanta, GA, USA, 1996. * |
D.W. Matson et al., "Rapid Expansion of supercritical Fluid Solutions: Solute Formation of Powders, Thin Films, and Fibers", Ind. Eng. Chem. Res., 1987, vol. 26, No. 11, pp. 2298-2306. |
D.W. Matson et al., Rapid Expansion of supercritical Fluid Solutions: Solute Formation of Powders, Thin Films, and Fibers , Ind. Eng. Chem. Res. , 1987, vol. 26, No. 11, pp. 2298 2306. * |
S. Mawson et al., "Formation of Poly(1,1,2,2-tetrahydroperfluorodecyl acrylate) Submicron Fibers and Particles from Supercritical Carbon Dioxide Solutions", Macromolecules, 1995, vol. 28, No. 9, pp. 3182-3191. |
S. Mawson et al., Formation of Poly(1,1,2,2 tetrahydroperfluorodecyl acrylate) Submicron Fibers and Particles from Supercritical Carbon Dioxide Solutions , Macromolecules , 1995, vol. 28, No. 9, pp. 3182 3191. * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6132653A (en) * | 1995-08-04 | 2000-10-17 | Microcoating Technologies | Chemical vapor deposition and powder formation using thermal spray with near supercritical and supercritical fluid solutions |
US20030054957A1 (en) * | 2001-07-12 | 2003-03-20 | Irvin Glen C. | Surfactant assisted nanomaterial generation process |
US7276184B2 (en) | 2001-07-12 | 2007-10-02 | Eastman Kodak Company | Surfactant assisted nanomaterial generation process |
US20060029676A1 (en) * | 2004-08-03 | 2006-02-09 | Clemson University | Aqueous suspension of nanoscale drug particles from supercritical fluid processing |
US7754243B2 (en) | 2004-08-03 | 2010-07-13 | Clemson University Research Foundation | Aqueous suspension of nanoscale drug particles from supercritical fluid processing |
US20060275542A1 (en) * | 2005-06-02 | 2006-12-07 | Eastman Kodak Company | Deposition of uniform layer of desired material |
WO2008006691A1 (en) * | 2006-07-13 | 2008-01-17 | Unilever N.V. | Surface-active material and its applications |
US20110236818A1 (en) * | 2010-03-25 | 2011-09-29 | Masahide Yamada | Method for preparing particulate release agent, toner using the particulate release agent, and method for preparing the toner |
US8580476B2 (en) * | 2010-03-25 | 2013-11-12 | Ricoh Company, Ltd. | Method for preparing particulate release agent, toner using the particulate release agent, and method for preparing the toner |
US20160143134A1 (en) * | 2014-11-17 | 2016-05-19 | Ibiden Co., Ltd. | Wiring board with built-in metal block and method for manufacturing the same |
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