WO1995031498A1 - Gels microporeux a reponse rapide et leurs procedes d'utilisation - Google Patents

Gels microporeux a reponse rapide et leurs procedes d'utilisation Download PDF

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Publication number
WO1995031498A1
WO1995031498A1 PCT/US1994/005400 US9405400W WO9531498A1 WO 1995031498 A1 WO1995031498 A1 WO 1995031498A1 US 9405400 W US9405400 W US 9405400W WO 9531498 A1 WO9531498 A1 WO 9531498A1
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WIPO (PCT)
Prior art keywords
gel
microporous
polymer
gels
phase separation
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Application number
PCT/US1994/005400
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English (en)
Inventor
Bhagwati G. Kabra
Stevin Henry Gehrke
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University Of Cincinnati
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Filing date
Publication date
Application filed by University Of Cincinnati filed Critical University Of Cincinnati
Priority to US08/737,404 priority Critical patent/US6030442A/en
Priority to AU70940/94A priority patent/AU7094094A/en
Priority to PCT/US1994/005400 priority patent/WO1995031498A1/fr
Publication of WO1995031498A1 publication Critical patent/WO1995031498A1/fr

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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
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • 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
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C08J3/075—Macromolecular gels
    • 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
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/28—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • C08L1/26—Cellulose ethers
    • C08L1/28—Alkyl ethers
    • C08L1/284—Alkyl ethers with hydroxylated hydrocarbon radicals
    • 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
    • C08J2300/00—Characterised by the use of unspecified polymers
    • C08J2300/10—Polymers characterised by the presence of specified groups, e.g. terminal or pendant functional groups

Definitions

  • variables that may be altered include: (i) increasing the concentration of crosslinker; (ii) increasing the reaction catalyst, if any, which would alter the rate of crosslinking relative to the rate of phase separation; (iii) increasing the rate and extent of phase separation, which would alter the rate of crosslinking relative to the rate of phase separation as well as possibly altering the type of phase separation which could alter the microstructure; and/or (iv) altering the solvent.
  • the concentrated solution of solute is separated from the swollen gel and the swollen gel is washed to yield a wash solution that is optionally combined with the concentrated solution of solute.
  • a volumetric change i.e., a collapse
  • This procedure may generally be used to exclude dissolved solutes or suspended particles, for example, in the dewatering of slurries.
  • the present gels may also be used in an apparatus for removing vapor from a gas stream.
  • the apparatus includes a housing adapted for movement from a first position, where it is exposed to the gas stream and to a first environmental condition, and then to a second position, where it is exposed to a second environmental condition. Also included is a means for moving the housing from the first to the second position.
  • a microporous, fast response, crosslinked gel of the invention is disposed on at least one surface of the housing, the gel capable of sorbing vapor from the gas stream as liquid when the housing is in the first position and capable of disgorging the liquid when the housing is in the second position.
  • fast response means that the gel reaches 90% of its maximum volumetric swelling or 90% of its minimum volumetric collapse in a time that is at least ten times faster than a comparable non-porous gel of the same geometry when both gels are subjected to a similar change in an environmental condition.
  • the primary requirement of a gel of the invention is that the entire gel, or its reversible volume change component, undergo a fast volume change.
  • the gel as a whole must meet these requirements. Nevertheless, the gel may itself include several other components as long as at least one component(s) provides the required property.
  • the fast response gel may also be an interpenetrating polymer network (IPN) in which at least one polymer interpenetrates at least another polymer.
  • An IPN may possess only a fast volume change property such as an IPN of poly-N isopropylamide.
  • a fast response IPN gel may also be combined (e.g. co-polymerized) with a sorptive- type gel to meet the requirements of vapor extraction, drug delivery, or other delivery system.
  • a purely fast response IPN may itself be combined in an IPN with a "sorptive" component.
  • the IPN may possess both properties, however, so that one polymer member of the IPN provides the sorptive property and the other polymer member provides the fast volume change property. This type of configuration is particularly useful in dehumidification/vapor extraction processes.
  • any of a variety of environmental conditions may be imposed on the gel which allows the specific trigger to induce a phase-transition.
  • These environmental conditions may, but not necessarily, be the same as the trigger and include, but are not limited to, a change in temperature, electric field, photon energy, pH, solvent composition, ion concentration, concentration of biomolecules, pressure, and the like.
  • Another method is to disperse solid particles in a polymer melt or in a polymer solution.
  • the polymer solution or melt is solidified either by chemical crosslinking or by physical means such as freezing. After solidification of the polymer, the solid particles are leached away. See Mikos et al, Mater. Res. Soc. Symp. Proc, 252, pp. 353-358 1992., incorporated herein by reference.
  • Vinyl polymers such as polyacrylamides or polyacrylates can be made "increasingly hydrophobic” by copolymerizing a hydrophilic monomer like acrylamide with a comparatively hydrophobic monomer like hydroxypropyl acrylate.
  • Hydrophilic natural polymers like cellulose or linear synthetic polymers like poly (vinyl alcohol) can be made “increasingly hydrophobic” by reaction with chemicals that convert hydrophilic polymeric side groups like hydroxyls to more hydrophobic ones like methoxy or hydroxypropyl.
  • Critical to the methods described herein is the regulation of polymerization in a manner that avoids formation of a rigid microstructure, i.e., an inflexible microstructure that will not allow the gel to undergo reversible volume change.
  • polymerization is continued for a time and under conditions needed for the gel network to obtain sufficient flexibility to undergo expansion and contraction in response to a changing condition i.e., a reversible volume change. Conditions needed to ensure this flexibility will vary. Nonetheless, using the procedures developed herein, one skilled in the art could test the efficacy of a particular method.
  • the gel solution may also be formed into beads or spheres using crosslinking in a non- solid mold where the reacting solution (polymer precursor, crosslinker and catalysis, if needed) is dispersed in a non ⁇ solvent to form a droplet.
  • the solution reacts within the droplet to form a bead.
  • the bead may be heated to induce phase separation to produce gel beads of the invention.
  • the non-solvent may be considered to be a "mold" for droplets. See, for example U.S. Patent 3,953,360, incorporated herein by reference.
  • the gel be crosslinkable, preferably chemically cross-linkable. Any reagent which can react with two or more groups on the polymer can function as a crosslinker and convert that polymer to a gel. Polymers with reactive side groups like hydroxyl, amide, or carboxyl will be among the easiest to crosslink (note that these groups are also water soluble groups) . It is thus most convenient if the crosslinker is water-soluble.
  • Dynamic Gravimetric Technique To measure the volume change by the dynamic gravimetric technique, a rectangular gel sheet ranging in thickness from 0.75 to 1.6 mm with a minimum aspect ratio (length to thickness) of 10 was immersed in distilled water in a capped jar at a predetermined temperature and allowed to reach equilibrium. Its equilibrium weight and thickness were noted down. Then it was kept in a temperature controlled water bath (Neslab 220, ⁇ 0.1°C) at another temperature. A Mettler analytical balance (AE 200, precision ⁇ 0.0001 g) was used to weigh the sample, and a micrometer (precision ⁇ 0.01 mm) was used to measure the thickness of the sample.
  • AE 200 precision ⁇ 0.0001 g
  • Example V Effect of Variables on Gel Microstructure Effect of Initial Polymer Concentration: In order to vary the microstructural characteristics such as porosity, pore size and strut size, the initial polymer concentration (C p ) was varied. The synthesis parameters and microstructural parameters obtained using the experimental procedure described above are summarized in Table 1.
  • the porosity of the gels did not change much with an increase in t BP up to 20 minutes (compare columns 2 and 3 of Table 2) , though the pores and struts decreased significantly. After 20 minutes, the porosity decreased and became zero at 60 minutes.
  • the pores and struts can be effectively controlled by ' varying t BP until gelation occurs while keeping the pore interconnectivity intact. By increasing t BP beyond gelation time, a microporous gel with unconnected pores can be prepared.
  • phase separation time (t DP ) was very small for gels P45, P75 and P76, after phase separation for this short period, lowering the crosslinking reaction temperature to room temperature caused remixing of the phase separated state.
  • the polymer concentration in the struts at the time of synthesis didn't increase much and the polymer concentration at the time of network formation is rather uniform, unlike the microporous gels which may have regions of different polymer concentration at the time of network formation.
  • the lower polymer concentration leads to a large change in the volume of the gel with temperature and the uniform polymer concentration leads to a sharp change in the volume of the gel near the transition temperature.
  • the transition temperature of these gels is remarkably close to homogenous gels with polymer volume fraction of about 0.16.
  • the rate of convection depends upon the pore size and the porosity. For a microporous interconnected gel, the rate of convection is faster than the rate of heat transfer for gels with maximum pore size greater than 0.2 ⁇ m and porosity greater than 0.5; as well as gels with a porosity greater than 0.2 and maximum pore sizes greater than 2.0 urn. Both the rate of convection and the rate of heat transfer vary inversely with the square of thickness. Hence the ratio of rate of convection to that of heat transfer should not change with the thickness.
  • the rate of convection will remain faster than the rate of heat transfer irrespective of gel thickness as long as the pores are interconnected and the pore size is greater than 0.2 ⁇ m for porosity greater than 0.5 or pore size is greater than 2.0 ⁇ m for porosity less than 0.5 but greater than 0.2.
  • the minimum likely value of the diffusion coefficient for rubbery gels is 1 x 10- 7 cm 2 /s.
  • the rate of heat transfer for microporous HPC gels can be given by a thermal diffusion coefficient of 1 x 10- 3 cm/s. Hence: 1 x 10- 3 ⁇ 1 x 10- 7
  • the response rate may be obtained by altering the gel microstructure. If all the pores are interconnected, the volume change can be altered either by slowing down the rate of network motion or the rate of convection.
  • the rate of network motion can be slowed down by simply increasing the strut thickness.
  • the volume change kinetics can be varied from the fast extreme to the slow extreme.
  • the strut thickness was always less than 0.01 x gel thickness, hence, the volume change kinetics could not be varied by changing the strut thickness.
  • the rate of convection can be decreased either by reducing the pore size of the porosity.
  • the pore size and porosity was always larger than what is required to decrease convection rate below the heat transfer rate.
  • the diffusion coefficient during swelling and shrinking changes as the polymer volume fraction changes.
  • the coefficient applicable to the entire phase transition cycle was taken as the average of the two diffusion coefficients; 7.5 x 10" 6 cm 2 /sec.
  • Volume change kinetics of gel P46 in response to a change in external ammonium sulfate were measured using the videomicroscopy method described above. As seen in Figure 10, this microporous gel responds about 50 to 100 times faster than what is expected for a non-porous gel.
  • the time needed for polymer network motion was estimated to be about 0.1 seconds, much shorter than the time needed for the volume change and implies that polymer network motion does not limit the volumetric kinetics of this ionic strength sensitive gel.
  • Thermally sensitive microporous gels with interconnected pores have volume change kinetics many times faster than non-porous gels. Kinetics of gels with interconnected pores are much faster due to the convective flow of solvent through the interconnected pores. The pores have to be interconnected to allow this flow and hence, to obtain faster volume change kinetics. When the pores are unconnected, there can be no convective flow through them and volume change kinetics is controlled by the rate of network motion.
  • the upper bound on the volume change kinetics is the rate of heat transfer and is observed in microporous gels with interconnected pores. Intermediate volume change kinetics was observed when the pores were partially connected, and in principle could be observed for microporous gels with strut thickness greater than 0.01 times gel thickness, but less than the gel thickness.
  • the microporous gel swollen with solvent and small solutes may be warmed so that it will rapidly undergo a phase transition collapse (within 30 seconds) to release the absorbed solvent.
  • the swollen gel may be washed with solution to yield a wash solution that is combined with the unabsorbed solution. This combined solution may be further subject to fast response gel treatment, as above.
  • Solvent is selectively absorbed by the fast response polymer and the coal-laden remaining in solution is separated from the solvent-laden fast response gel.
  • the present gels may also be used to separate solvent (mainly water) from suspended sludge in sewage treatment facilities, or to separate dissolved ink from solvent in paper pulp waste generated by paper-making procedures, or separate dissolved or suspended solutes from solvents in chemical process waste streams, or separate solutes from seawater.
  • An exemplary apparatus for extracting vapor from a gas stream includes a microporous, reversibly responsive, fast response gel of the invention that is capable of sorbing vapor as a liquid when exposed to a first environmental condition and capable of disgorging the liquid when exposed to a second environmental condition.
  • the fast response gel is moved by way of a housing from a first position, where it is exposed to a gas stream and exposed to a first environmental condition (i.e., a first temperature), and then to a second position, where it is exposed to a second environmental condition (i.e., a second temperature).
  • the first environmental condition may allow for sorption of the vapor and rapid expansion of the gel and the second environmental condition causes the gel to rapidly collapse and disgorge the liquid.
  • the fast response gel can also be an interpenetrating network of two or more polymers whose rapid and reversible responsiveness is initiated by a change, relative to the first environmental condition, in at least one of temperature, pH, solvent concentration and ion concentration.
  • the housing may be a thin disk having perforations defined in it for holding the fast response gel.
  • the housing can be a disk having many gel-lined cells defined in it that are arranged in a honeycomb configuration. See, for example, U.S. Patent 3,140,936, incorporated herein by reference.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

Abstract

Un gel microporeux, réticulé, sensible de façon réversible, peut être obtenu à partir d'un précurseur polymère. Les gels microporeux présentent une réponse de variation de volume de l'ordre de quelques secondes, et sont bien plus rapides que les gels à variation de volume non poreux, de dimensions similaires. L'invention se rapporte également à un procédé de fabrication d'un gel microporeux, réticulé, sensible de façon réversible, présentant une grosseur de pore définie et une épaisseur d'entrecroisement définie. Ce procédé consiste à préparer une solution polymère possédant une certaine concentration initiale de précurseur polymère; à déclencher la séparation de phase du polymère pour obtenir un état de séparation de phase; à réticuler le polymère au cours de son état de séparation de phase ou avant celui-ci, ou bien à la fois avant et pendant son état de séparation de phase, pendant un certain temps de réaction de réticulation; et à réaliser la gélification. L'invention se rapporte, en outre, à des utilisations particulières de gels à réponse rapide. Selon un mode de réalisation, on décrit un procédé de purification et de concentration d'un soluté à partir d'une solution. Ce procédé consiste à mettre en contact une solution contenant le soluté avec le gel microporeux de l'invention. Puis le gel est gonflé afin d'absorber une partie de la solution et d'exclure le soluté en déclenchant la dilatation. Ceci se traduit par l'obtention d'une solution concentrée de soluté et d'un gel microporeux, gonflé à la base par un soluté dépourvu de solution.
PCT/US1994/005400 1994-05-13 1994-05-13 Gels microporeux a reponse rapide et leurs procedes d'utilisation WO1995031498A1 (fr)

Priority Applications (3)

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US08/737,404 US6030442A (en) 1994-05-13 1994-05-13 Microporous fast response gels and methods of use
AU70940/94A AU7094094A (en) 1994-05-13 1994-05-13 Microporous fast response gels and methods of use
PCT/US1994/005400 WO1995031498A1 (fr) 1994-05-13 1994-05-13 Gels microporeux a reponse rapide et leurs procedes d'utilisation

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5827459A (en) * 1995-03-15 1998-10-27 Acushnet Company Conforming shoe construction using gels and method of making the same
US5976648A (en) * 1995-12-14 1999-11-02 Kimberly-Clark Worldwide, Inc. Synthesis and use of heterogeneous polymer gels
US6048908A (en) * 1997-06-27 2000-04-11 Biopore Corporation Hydrophilic polymeric material
US6100306A (en) * 1994-06-06 2000-08-08 Biopore Corporation Polymeric microbeads and methods of preparation
EP1065743A2 (fr) * 1999-06-30 2001-01-03 Mitsubishi Materials Corporation Batterie secondaire polymère à ions lithium et électrolyte polymère du type gel pour batterie mince

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JPS6155180A (ja) * 1984-08-17 1986-03-19 マサチユ−セツツ　インステイチユ−ト　オブ　テクノロジ− 非イオンゲル
EP0213908A2 (fr) * 1985-08-26 1987-03-11 Hana Biologics, Inc. Tissu artificiel transplantable et procédé
JPS62250940A (ja) * 1986-04-23 1987-10-31 Agency Of Ind Science & Technol 温度応答性多孔質ゲル及びその製造方法
JPH01270936A (ja) * 1988-04-22 1989-10-30 Agency Of Ind Science & Technol 温度応答性多孔質ゲルの製造方法
US5100933A (en) * 1986-03-31 1992-03-31 Massachusetts Institute Of Technology Collapsible gel compositions

Patent Citations (5)

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Publication number Priority date Publication date Assignee Title
JPS6155180A (ja) * 1984-08-17 1986-03-19 マサチユ−セツツ　インステイチユ−ト　オブ　テクノロジ− 非イオンゲル
EP0213908A2 (fr) * 1985-08-26 1987-03-11 Hana Biologics, Inc. Tissu artificiel transplantable et procédé
US5100933A (en) * 1986-03-31 1992-03-31 Massachusetts Institute Of Technology Collapsible gel compositions
JPS62250940A (ja) * 1986-04-23 1987-10-31 Agency Of Ind Science & Technol 温度応答性多孔質ゲル及びその製造方法
JPH01270936A (ja) * 1988-04-22 1989-10-30 Agency Of Ind Science & Technol 温度応答性多孔質ゲルの製造方法

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Title
DATABASE WPI Week 8618, Derwent World Patents Index; AN 115572 *
PATENT ABSTRACTS OF JAPAN vol. 12, no. 132 (C - 490) 22 April 1988 (1988-04-22) *
PATENT ABSTRACTS OF JAPAN vol. 14, no. 34 (C - 679) 23 January 1990 (1990-01-23) *
STEVIN H. GEHRKE: "Synthesis, Equilibrium Swelling, Kinetics, Permeability and Applications of Environmentally Responsive Gels", ADVANCES IN POLYMER SCIENCE ; RESPONSIVE GELS VOLUME TRANSACTIONS II, vol. 110, 1993, HEIDELBERG, pages 83 - 144 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6100306A (en) * 1994-06-06 2000-08-08 Biopore Corporation Polymeric microbeads and methods of preparation
US5827459A (en) * 1995-03-15 1998-10-27 Acushnet Company Conforming shoe construction using gels and method of making the same
US5976648A (en) * 1995-12-14 1999-11-02 Kimberly-Clark Worldwide, Inc. Synthesis and use of heterogeneous polymer gels
US6194073B1 (en) 1995-12-14 2001-02-27 Kimberly-Clark Worldwide, Inc Synthesis and use of heterogeneous polymer gels
US6048908A (en) * 1997-06-27 2000-04-11 Biopore Corporation Hydrophilic polymeric material
US6218440B1 (en) 1997-06-27 2001-04-17 Biopore Corporation Hydrophilic polymeric material and method of preparation
EP1065743A2 (fr) * 1999-06-30 2001-01-03 Mitsubishi Materials Corporation Batterie secondaire polymère à ions lithium et électrolyte polymère du type gel pour batterie mince
EP1065743A3 (fr) * 1999-06-30 2004-03-17 Mitsubishi Materials Corporation Batterie secondaire polymère à ions lithium et électrolyte polymère du type gel pour batterie mince
EP1686639A1 (fr) * 1999-06-30 2006-08-02 Mitsubishi Materials Corporation Batterie secondaire polymère à ions lithium et électrolyte polymère du type gel pour batterie mince

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