WO1992013566A1 - Gels a transition de phases et reseau polymere d'interpenetration - Google Patents

Gels a transition de phases et reseau polymere d'interpenetration Download PDF

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Publication number
WO1992013566A1
WO1992013566A1 PCT/US1992/000797 US9200797W WO9213566A1 WO 1992013566 A1 WO1992013566 A1 WO 1992013566A1 US 9200797 W US9200797 W US 9200797W WO 9213566 A1 WO9213566 A1 WO 9213566A1
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WO
WIPO (PCT)
Prior art keywords
gel
phase
transition
polymer network
chemical
Prior art date
Application number
PCT/US1992/000797
Other languages
English (en)
Inventor
Toyoichi Tanaka
Franck Ilmain
Etsuo Kokufuta
Masahiko Annaka
Original Assignee
Massachusetts Institute Of Technology
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 Massachusetts Institute Of Technology filed Critical Massachusetts Institute Of Technology
Priority to JP4505737A priority Critical patent/JPH06506490A/ja
Publication of WO1992013566A1 publication Critical patent/WO1992013566A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds

Definitions

  • the chemical bond can be between the component to be separated from the solution and any of the polymers of the interpenetrating polymer network, to thereby cause a phase transition of the polymer network and, consequently, cause a phase transition of the gel.
  • interaction between a component in a liquid medium within the interpenetrating polymer network and the interpenetrating polymer network can cause an interaction between the polymers of the interpenetrating polymer network which, in turn, causes a phase transition of the gel.
  • the component can be separated from the solution by contraction of the gel during phase transition by entrapment of the component in the gel or by binding to the polymer network in the gel.
  • Figure 5 is a plot of phase transitions for interpenetrating polymer network gels of poly(acrylic acid) and poly(aerylamide) in water wherein the gels have been ionized in varying degrees and wherein the phase transitions are a result of hydrogen bonding between the interpenetrating polymers.
  • the shaded area represents a region of discontinuous volume change of the gel.
  • the dotted lines represent discontinuities in the phase state of a given polymer with a fixed ionization.
  • Phase-transition of gels, as that term is used herein, means a significantly large rate of volume change of gels between an expanded phase and a contracted phase or vice-versa.
  • Phase-transition gels are gels which exhibit a phase transition at a phase-transition condition. The difference in volume between the expanded phase of phase-transition gels and the contracted phase of the phase-transition gels can be hundreds of orders of magnitude. Examples of phase-transition gels are disclosed in Tanaka et al. , U.S. Patent No. 4,732,930 and U.S. Patent Applications 07/425,788, 07/470,977 and 07/558,733, the teachings of which are incorporated herein by reference.
  • the phase-transition gels of the present invention undergo a significantly large rate of volume change at a desired phase-transition condition in response to a stimulus.
  • the phase-transition gel includes an interpenetrating polymer network gelled with a liquid medium.
  • Phase-transition conditions at which the phase-transition gels exhibit a significantly large volume change can include physical conditions, chemical conditions, or combinations of physical and chemical conditions.
  • physical phase-transition conditions include: temperature; electromagnetic radiation, such as infrared energy, visible light and ultraviolet light; etc.
  • chemical phase-transition conditions include: concentration of ionic species, such as hydrogen and water, i.e. pH; crosslinking agents, such as cross-linking agents which crosslink the polymer network of the phase-transition gel; inorganic and organic solvents; specific chemicals; etc.
  • Phase-transition conditions at which the phase-transition gels exhibit a significantly large volume change can include combinations of physical conditions, combinations of chemical conditions, or combinations of physical and chemical conditions.
  • incorporación of acidic and basic polymers into the interpenetrating polymer network causes ions in the absorbed liquid, such as sodium ions and chloride ions, to become bonded to the polymers, thereby reducing osmotic pressure caused by the ions and enabling phase transition for absorption of fluids containing relatively high concentrations of ions.
  • a gel includes an interpenetrating polymer network of an anionic poly(acrylic acid) and a cationic poly(methacrylamidopropyl-trimethyl-ammonium-chloride) (poly(MAPTAC)) in water. This gel swells about tenfold in salt solutions having concentrations greater than about lOOmM.
  • Another example of a suitable gel includes an interpenetrating polymer gel of poly(styrene sulfuric acid) and poly(MAPTAC) . It is to be understood, however, that any combination of acidic and basic polymers can be used.
  • interpenetrating polymer network gels can be designed to recognize hydrogen, hydrophobic interactions, ions, and van der Waals forces, it is conceivable that custom-engineered interpenetrating polymer network gels can be created to recognize specific molecules that have given sequences. An application of this would be a gel to absorb microbial toxins from a bacteria, toxin, virus or other microorganism that is causing diarrhea. By absorbing the toxin, the toxin would not be available to irritate the gastrointestinal tract.
  • Gel 1 Three different gels were formed comprising interpenetrating polymer networks of poly(acrylamide) and poly(acrylic acid).
  • Gel 1 was formed without ionization of either polymer in the interpenetrating polymer network.
  • Three percent and six percent respectively, of the acrylic acid groups in the poly(acrylic acid) of Gels 2 and 3 were ionized.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention décrit un gel à interpénétration et un procédé de formation d'un gel à interpénétration subissant une modification de volume importante en réaction à une stimulation physique ou chimique.
PCT/US1992/000797 1991-01-31 1992-01-31 Gels a transition de phases et reseau polymere d'interpenetration WO1992013566A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP4505737A JPH06506490A (ja) 1991-01-31 1992-01-31 相互貫通性重合体網目構造体相転移ゲル

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US64856391A 1991-01-31 1991-01-31
US648,563 1991-01-31

Publications (1)

Publication Number Publication Date
WO1992013566A1 true WO1992013566A1 (fr) 1992-08-20

Family

ID=24601309

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1992/000797 WO1992013566A1 (fr) 1991-01-31 1992-01-31 Gels a transition de phases et reseau polymere d'interpenetration

Country Status (3)

Country Link
EP (1) EP0569542A1 (fr)
JP (1) JPH06506490A (fr)
WO (1) WO1992013566A1 (fr)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995030411A1 (fr) * 1994-05-09 1995-11-16 Korea Research Institute Of Chemical Technology Systeme d'administration de medicaments par voie transdermique, possedant des reseaux polymeres ioniques
WO1996002239A2 (fr) * 1994-07-18 1996-02-01 University Of Cincinnati Amelioration du chargement de solutes dans des gels polymeres et procedes d'utilisation
WO1996006134A1 (fr) * 1994-08-19 1996-02-29 Gel Sciences, Inc. Gels reactionnels eliminant une cible selectivement d'un environnement et procedes afferents
EP0734286A1 (fr) * 1993-12-15 1996-10-02 Gel Sciences, Inc. Extracteur de vapeur a base de gel et procedes associes
US5612384A (en) * 1994-09-13 1997-03-18 Donlar Corporation Superabsorbing polymeric networks
US5759524A (en) * 1996-02-09 1998-06-02 The Procter & Gamble Company Photoprotective compositions
US5804173A (en) * 1996-09-04 1998-09-08 The Procter & Gamble Company Personal care compositions
US5824666A (en) * 1994-03-11 1998-10-20 The Procter & Gamble Company Low PH, hydrolytically stable, cosmetic compositions containing acidic actives
US5830447A (en) * 1996-09-04 1998-11-03 The Procter & Gamble Company Personal care compositions
US5840338A (en) * 1994-07-18 1998-11-24 Roos; Eric J. Loading of biologically active solutes into polymer gels
US5843089A (en) * 1990-12-28 1998-12-01 Boston Scientific Corporation Stent lining
US5863527A (en) * 1996-09-04 1999-01-26 The Proctor & Gamble Company Personal care compositions
US5868719A (en) * 1997-01-15 1999-02-09 Boston Scientific Corporation Drug delivery balloon catheter device
US5916548A (en) * 1996-09-04 1999-06-29 The Procter & Gamble Company Personal care compositions
US5948416A (en) * 1995-06-29 1999-09-07 The Procter & Gamble Company Stable topical compositions
US5954706A (en) * 1990-12-28 1999-09-21 Boston Scientific Corporation Drug delivery
US5998492A (en) * 1994-09-13 1999-12-07 Donlar Corporation Super-absorbing polymeric networks
US6494861B1 (en) 1997-01-15 2002-12-17 Boston Scientific Corporation Drug delivery system
US6524274B1 (en) 1990-12-28 2003-02-25 Scimed Life Systems, Inc. Triggered release hydrogel drug delivery system
WO2003093327A1 (fr) * 2002-05-01 2003-11-13 Hokkaido Technology Licensing Office Co., Ltd. Gel ayant une structure multiple en réseau et procédé de production
US8025696B2 (en) 2004-06-18 2011-09-27 National University Corporation Hokkaido University Artificial meniscus and process of making thereof
US9943668B2 (en) 2010-07-16 2018-04-17 Sub3 Vascular, Llc Guidewire and catheter system and method for treating a blood clot

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4732930A (en) * 1985-05-20 1988-03-22 Massachusetts Institute Of Technology Reversible, discontinuous volume changes of ionized isopropylacrylamide cells
WO1989007455A1 (fr) * 1988-02-12 1989-08-24 Zaepffel Brigitte Copolymere hydrophile reticule a usage medical et paramedical
EP0347145A2 (fr) * 1988-06-14 1989-12-20 University Of Utah Research Foundation Réseaux polymères hétérogènes interpénétrants pour la libération commandée de substances pharmaceutiques
EP0411621A2 (fr) * 1989-08-04 1991-02-06 Senju Pharmaceutical Co., Ltd. Hydrogel électrorépondeur et système commandé pour la libération de substances physiologiquement actives

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4732930A (en) * 1985-05-20 1988-03-22 Massachusetts Institute Of Technology Reversible, discontinuous volume changes of ionized isopropylacrylamide cells
WO1989007455A1 (fr) * 1988-02-12 1989-08-24 Zaepffel Brigitte Copolymere hydrophile reticule a usage medical et paramedical
EP0347145A2 (fr) * 1988-06-14 1989-12-20 University Of Utah Research Foundation Réseaux polymères hétérogènes interpénétrants pour la libération commandée de substances pharmaceutiques
EP0411621A2 (fr) * 1989-08-04 1991-02-06 Senju Pharmaceutical Co., Ltd. Hydrogel électrorépondeur et système commandé pour la libération de substances physiologiquement actives

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
JOURNAL OF CHEMICAL PHYSICS vol. 89, no. 3, August 1988, WOODBURY pages 1695 - 1703; MATSUO E.S. ET AL: 'kinetics of discontinous volume-phase transition of gels' *
JOURNAL OF CONTROLLED RELEASE vol. 11, 1990, AMSTERDAM pages 255 - 265; OKANO T. ET AL: 'thermally on-off switching polymers for drug permeation and release' *
JOURNAL OF CONTROLLED RELEASE vol. 16, June 1991, AMSTERDAM pages 215 - 228; KATANO H. ET AL: 'Thermo-responsive swelling and drug release switchiing of interpenetrating polymer networks composed of poly(acrylamide-co-butyl methacrylate) and poly(acrylic acid)' *
PATENT ABSTRACTS OF JAPAN vol. 15, no. 104 (C-814)13 March 1991 & JP,A,3 002 211 ( DAIKIN IND LTD ) 8 January 1991 *
POLYMER SCIENCE USSR vol. 23, no. 6, 1982, POLAND pages 1439 - 1446; KLENINA O.V. ET AL: 'phase separation in the system polyacrylic acid-polyacrylamide-water' *
WORLD PATENTS INDEX LATEST Section Ch, Week 9120, Derwent Publications Ltd., London, GB; Class A, AN 91-143954 & JP,A,3 079 608 (SHINGIJUTSU KAIHATSU) 4 April 1991 *

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6409716B1 (en) 1989-12-15 2002-06-25 Scimed Life Systems, Inc. Drug delivery
US6524274B1 (en) 1990-12-28 2003-02-25 Scimed Life Systems, Inc. Triggered release hydrogel drug delivery system
US5954706A (en) * 1990-12-28 1999-09-21 Boston Scientific Corporation Drug delivery
US6364893B1 (en) 1990-12-28 2002-04-02 Scimed Life Systems, Inc. Stent lining
US7066904B2 (en) 1990-12-28 2006-06-27 Boston Scientific Scimed, Inc. Triggered release hydrogel drug delivery system
US5843089A (en) * 1990-12-28 1998-12-01 Boston Scientific Corporation Stent lining
EP0734286A1 (fr) * 1993-12-15 1996-10-02 Gel Sciences, Inc. Extracteur de vapeur a base de gel et procedes associes
EP0734286A4 (fr) * 1993-12-15 1997-05-07 Gel Sciences Inc Extracteur de vapeur a base de gel et procedes associes
US5824666A (en) * 1994-03-11 1998-10-20 The Procter & Gamble Company Low PH, hydrolytically stable, cosmetic compositions containing acidic actives
WO1995030411A1 (fr) * 1994-05-09 1995-11-16 Korea Research Institute Of Chemical Technology Systeme d'administration de medicaments par voie transdermique, possedant des reseaux polymeres ioniques
US5674521A (en) * 1994-07-18 1997-10-07 University Of Cincinnati Enhanced loading of solutes into polymer gels and methods of use
US5603955A (en) * 1994-07-18 1997-02-18 University Of Cincinnati Enhanced loading of solutes into polymer gels
WO1996002239A3 (fr) * 1994-07-18 1997-02-13 Univ Cincinnati Amelioration du chargement de solutes dans des gels polymeres et procedes d'utilisation
WO1996002239A2 (fr) * 1994-07-18 1996-02-01 University Of Cincinnati Amelioration du chargement de solutes dans des gels polymeres et procedes d'utilisation
US5840338A (en) * 1994-07-18 1998-11-24 Roos; Eric J. Loading of biologically active solutes into polymer gels
WO1996006134A1 (fr) * 1994-08-19 1996-02-29 Gel Sciences, Inc. Gels reactionnels eliminant une cible selectivement d'un environnement et procedes afferents
EP0785958A1 (fr) * 1994-09-13 1997-07-30 Donlar Corporation Reseaux polymeres surperabsorbants
US5612384A (en) * 1994-09-13 1997-03-18 Donlar Corporation Superabsorbing polymeric networks
EP0785958A4 (fr) * 1994-09-13 1998-01-07 Donlar Corp Reseaux polymeres surperabsorbants
US5847013A (en) * 1994-09-13 1998-12-08 Donlar Corporation Superabsorbing polymeric networks
US5998492A (en) * 1994-09-13 1999-12-07 Donlar Corporation Super-absorbing polymeric networks
US5948416A (en) * 1995-06-29 1999-09-07 The Procter & Gamble Company Stable topical compositions
US6024942A (en) * 1996-02-09 2000-02-15 The Procter & Gamble Company Photoprotective compositions
US5759524A (en) * 1996-02-09 1998-06-02 The Procter & Gamble Company Photoprotective compositions
US5804173A (en) * 1996-09-04 1998-09-08 The Procter & Gamble Company Personal care compositions
US5830447A (en) * 1996-09-04 1998-11-03 The Procter & Gamble Company Personal care compositions
US5916548A (en) * 1996-09-04 1999-06-29 The Procter & Gamble Company Personal care compositions
US5863527A (en) * 1996-09-04 1999-01-26 The Proctor & Gamble Company Personal care compositions
US6494861B1 (en) 1997-01-15 2002-12-17 Boston Scientific Corporation Drug delivery system
US5868719A (en) * 1997-01-15 1999-02-09 Boston Scientific Corporation Drug delivery balloon catheter device
WO2003093327A1 (fr) * 2002-05-01 2003-11-13 Hokkaido Technology Licensing Office Co., Ltd. Gel ayant une structure multiple en réseau et procédé de production
KR101002147B1 (ko) 2002-05-01 2010-12-17 국립대학법인 홋가이도 다이가쿠 (세미)상호침입 메쉬 구조 하이드로겔 및 그의 제조 방법
US8029824B2 (en) 2002-05-01 2011-10-04 National University Corporation Hokkaido University Hydrogel of (semi) interpenetrating network structure and process for producing the same
US8025696B2 (en) 2004-06-18 2011-09-27 National University Corporation Hokkaido University Artificial meniscus and process of making thereof
US9943668B2 (en) 2010-07-16 2018-04-17 Sub3 Vascular, Llc Guidewire and catheter system and method for treating a blood clot

Also Published As

Publication number Publication date
JPH06506490A (ja) 1994-07-21
EP0569542A1 (fr) 1993-11-18

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