WO2011011658A1 - Adhesive complex coacervates and methods of making and using thereof - Google Patents

Adhesive complex coacervates and methods of making and using thereof Download PDF

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Publication number
WO2011011658A1
WO2011011658A1 PCT/US2010/043009 US2010043009W WO2011011658A1 WO 2011011658 A1 WO2011011658 A1 WO 2011011658A1 US 2010043009 W US2010043009 W US 2010043009W WO 2011011658 A1 WO2011011658 A1 WO 2011011658A1
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Prior art keywords
coacervate
polyanion
group
polycation
adhesive
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English (en)
French (fr)
Inventor
Russell John Stewart
Hui Shao
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University of Utah Research Foundation Inc
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University of Utah Research Foundation Inc
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Priority to JP2012521803A priority Critical patent/JP5928825B2/ja
Priority to CN2010800383973A priority patent/CN102548581A/zh
Priority to AU2010275504A priority patent/AU2010275504A1/en
Priority to EP10802933.1A priority patent/EP2456466B1/en
Priority to CA2768501A priority patent/CA2768501A1/en
Publication of WO2011011658A1 publication Critical patent/WO2011011658A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/0047—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
    • A61L24/0073—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material with a macromolecular matrix
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02—Prostheses implantable into the body
    • A61F2/28—Bones
    • A61F2/2846—Support means for bone substitute or for bone graft implants, e.g. membranes or plates for covering bone defects
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/001—Use of materials characterised by their function or physical properties
    • A61L24/0015—Medicaments; Biocides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
    • A61L24/043—Mixtures of macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14—Macromolecular materials
    • A61L27/26—Mixtures of macromolecular compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/54—Biologically active materials, e.g. therapeutic substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/06—Oxidation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/10—Acylation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/24—Homopolymers or copolymers of amides or imides
    • C08L33/26—Homopolymers or copolymers of acrylamide or methacrylamide
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/24—Homopolymers or copolymers of amides or imides
    • C09D133/26—Homopolymers or copolymers of acrylamide or methacrylamide
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
    • A61L2300/602—Type of release, e.g. controlled, sustained, slow
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
    • A61L2300/62—Encapsulated active agents, e.g. emulsified droplets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
    • C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00—Chemical modification of a polymer
    • C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00—Chemical modification of a polymer
    • C08F2810/30—Chemical modification of a polymer leading to the formation or introduction of aliphatic or alicyclic unsaturated groups

Definitions

  • Figure 12 shows the liquid character of an adhesive complex coacervate.
  • the solution of 1 and 2 contained equal quantities of amine and phosphate sidechains, pH
  • Figure 13 shows the phase diagram of polyelectrolytes and divalent cations.
  • the amine to phosphate sidechain and phosphate sidechain to divalent cation ratios were varied at a fixed pH 8.2.
  • the state of the solutions represented in a gray scale.
  • the mass (mg) of the coacervate phase is indicated in the dark grey squares.
  • the compositions indicated with an asterisk were used to test bond strength.
  • Figure 21 shows a reaction scheme for producing amine-modified gelatin.
  • Figure 22 shows (A) an example of an adhesive complex coacervate in water
  • Figure 24 shows the solidification temperature determined by dynamic oscillatory rheology.
  • A Ca 2+ /gelatin/polyphosphate rheology.
  • the elastic modulus (G', black symbol) increased sigmoidally as the temperature was raised from 0 to 40 0 C at Ca 2+ ratios greater than 0.15.
  • Inset The crossover of the elastic (G') and viscous (G", grey symbol) moduli, the solidification or gellation temperature, decreased with increasing Ca 2+ ratio. The 0.25 Ca 2+ ratio was excluded from the inset for clarity.
  • B Mg 2+ /gelatin/polyphosphate rheology.
  • the comparative measurements were made with constant strain of 0.1% and frequency of 1.0 hz.
  • Figure 25 shows the shear strength as a function of divalent cation ratio and temperature.
  • A The Ca 2+ ratio to phosphate was varied at a constant amine ratio.
  • Figure 26 shows the synthesis of polycations and polyanions with actinically crosslinkable groups and subsequent crosslinking of the polyacations and polyanions.
  • Ranges may be expressed herein as from “about” one particular value, and/or to "about” another particular value. When such a range is expressed, another aspect includes from the one particular value and/or to the other particular value. Similarly, when values are expressed as approximations, by use of the antecedent "about,” it will be understood that the particular value forms another aspect. It will be further understood that the endpoints of each of the ranges are significant both in relation to the other endpoint, and independently of the other endpoint.
  • the compound if it possesses a basic group, it can be protonated with an acid such as, for example, HCI, HBr, or H 2 SO 4 , to produce the cationic salt.
  • an acid such as, for example, HCI, HBr, or H 2 SO 4
  • the reaction of the compound with the acid or base is conducted in water, alone or in combination with an inert, water-miscible organic solvent, at a temperature of from about 0 0 C to about 100 0 C such as at room temperature.
  • the molar ratio of the compounds described herein to base used are chosen to provide the ratio desired for any particular salts.
  • the starting material can be treated with approximately one equivalent of pharmaceutically-acceptable base to yield a neutral salt.
  • the adhesive complex coacervate is an associative liquid with a dynamic structure in which the individual polymer components diffuse throughout the entire phase. Complex coacervates behave Theologically like viscous particle dispersions rather than a viscoelastic polymer solution. As described above, the adhesive complex coacervates exhibit low interfacial tension in water when applied to substrates either under water or that are wet. In other words, the complex coacervate spreads evenly over the interface rather than beading up. Additionally, upon intermolecular crosslinking, the adhesive complex coacervate forms a strong, insoluble, cohesive material.
  • electrophilic groups include, but are not limited to, anhydride groups, esters, ketones, lactams (e.g., maleimides and succinimides), lactones, epoxide groups, isocyanate groups, and aldehydes. Examples of nucleophilic groups are presented below.
  • olefinic groups useful herein include, but are not limited to, an acrylate group, a methacrylate group, an acrylamide group, a methacrylamide group, an allyl group, a vinyl group, a vinylester group, or a styrenyl group.
  • polymerization initiators to facilitate crosslinking is described in detail below.
  • the oxidant can be stabilized.
  • a compound that forms a complex with periodate that is not redox active can result in a stabilized oxidant.
  • the periodate is stabilized in a non-oxidative form and cannot oxidize the dihydroxyl-substituted aromatic group while in the complex.
  • the complex is reversible and even if it has a very high stability constant there is a small amount of uncomplexed periodate formed.
  • the stable but reversible oxidant permits the slow release of oxidant in order to control the rate of oxidative crosslinking.
  • the dihydroxyl-substituted aromatic group competes with the compound for the small amount of free periodate.
  • sugars possessing a cis,cis-l,2,3- triol grouping on a six-membered ring can form competitive periodate complexes.
  • An example of a specific compound that forms stable periodate complex is 1,2-0- isopropylidene-alpha-D-glucofuranose.
  • the stabilized oxidant can control the rate of crosslinking. Not wishing to be bound by theory, the stabilized oxidant slows it down the rate of oxidation so that there is time to add the oxidant and position the substrate before the adhesive hardens irreversibly.
  • the stability of the oxidized crosslinker can vary.
  • the phosphono containing polyanions described herein that contain oxidizable crosslinkers are stable in solution and do not crosslink with themselves.
  • nucleophilic groups that are useful include, but are not limited to, hydroxyl, thiol, and nitrogen containing groups such as substituted or unsubstituted amino groups and imidazole groups.
  • the polycation when the polycation is naturally-occurring, can be a positively-charged protein produced from a natural organism.
  • proteins produced by P. californica can be used as the polycation.
  • Figures 2-6 show the protein sequences of several cement proteins produced by P. californica (Zhao et al. "Cement Proteins of the tube building polychaete Phragmatopoma californica” /. Biol. Chem. (2005) 280: 42938-42944).
  • Figure 20 provides the amino acid mole % of each protein.
  • the biodegradable polyamine includes a polysaccharide, a protein, or a synthetic polyamine.
  • Polysaccharides bearing one or more amino groups can be used herein.
  • the polysaccharide is a natural polysaccharide such as chitosan.
  • the protein can be a synthetic or naturally-occurring compound.
  • the biodegradable polyamine is a synthetic polyamine such as poly( ⁇ -aminoesters), polyester amines, poly(disulfide amines), mixed poly(ester and amide amines), and peptide crosslinked polyamines. It is desirable in certain aspects that the polycation as well as the polyanion be non-gelling and a low- endotoxin.
  • phosphorous containing polymers can be converted to polyanions.
  • a phospholipid or phosphosugar is not a polyanion but it can be converted into a polyanion by creating a liposome or a micelle with it.
  • the complex coacervate is a charged colloid.
  • the colloid can be produced by any of the polyanions or polycations described herein.
  • an adhesive is produced by crosslinking the polycation and polyanion in the adhesive complex coacervate. Any of the techniques and approaches previously described herein can be used to crosslink the polycation and polyanion.
  • the adhesive can be produced by the process comprising:
  • oxidized crosslinkers e.g., DOPA or other catechols
  • oxidized crosslinkers can couple to nucleophilic sidechains of bone matrix proteins.
  • the scaffold can contain one or more drugs that facilitate growth or repair of the bone and tissue.
  • the scaffold can include drugs that prevent infection such as, for example, antibiotics.
  • the scaffold can be coated with the drug or, in the alternative, the drug can be incorporated within the scaffold so that the drug elutes from the scaffold over time.
  • the adhesive complex coacervates and adhesives produced therefrom can include one or more bioactive agents.
  • the bioactive agents can be any drug that will facilitate bone growth and repair when the complex is applied to the bone. The rate of release can be controlled by the selection of the materials used to prepare the complex as well as the charge of the bioactive agent if the agent is a salt.
  • the adhesive complex coacervate when the adhesive complex coacervate is converted to an insoluble solid by a change in temperature and/or pH, the complex coacervate can be administered to a subject and produce an insoluble solid in situ.
  • the insoluble solid can perform as a localized controlled drug release depot. It may be possible to simultaneously fix tissue and bones as well as deliver bioactive agents to provide greater patient comfort, accelerate bone healing, and/or prevent infections.
  • reaction conditions e.g., component concentrations, desired solvents, solvent mixtures, temperatures, pressures and other reaction ranges and conditions that can be used to optimize the product purity and yield obtained from the described process. Only reasonable and routine experimentation will be required to optimize such process conditions.
  • the dopa analog monomer (dopamine methacrylamide, DMA) was prepared by slight modification of a published procedure. (Lee BP, Huang K, Nunalee FN, Shull KR, Messersmith PB. Synthesis of 3,4-dihydroxyphenylalanine (DOPA) containing monomers and their co-polymerization with PEG-diacrylate to form hydrogels. J Biomater Sci Polym Ed 2004;15(4):449-464). Briefly, a borate- dopamine complex was reacted at pH >9 with methacryloyl chloride.
  • DOPA 3,4-dihydroxyphenylalanine
  • the copolymers were concentrated about three-fold to 148 and 153 mg/ml, respectively, in the coacervated phases.
  • the polyelectrolyte mixture formed a dense non-liquid ionic gel.
  • the copolymers went into solution and spontaneously crosslinked through the dopaquinone and amine sidechains into a clear hydrogel.
  • the cells were fixed with 4% para-formaldehdye, then immunostained for the intermediate filament protein, vimentin, to visualize cell morphology (green, A-B), pericellular fibronectin to assess ECM secretion (red, B), glial fibrillary protein to visual primary astrocyte morphology (green, C), and DAPI to visualize nuclei (blue,C).
  • Gelatin modification The general reaction scheme for producing amine-modified gelatin is provided in Figure 21. Gelatin (100 mg/ml) was mixed with
  • ethylenediamine dihydrochloride (1:1 molar ratio to the gelatin carboxyl groups). The pH was adjusted to 5.2 with 6M HCl. EDC at 1.2:1 molar ratio to ethylenediamine dihydrochloride was added to the reaction mixture while stirring. The reaction proceeded for 2 hrs at room temperature. The amine-modified gelatin was dialyzed against DI water for 3 days then lyophilized. The primary amine side chain concentration was determined by ninhydrin assay using glycine as a standard. Zeta potential measurements of gelatin (1 mg/ml in water) were determined by electrophoresis using a Malvern Zetasizer Nano-ZS ZEN 3600 (Malvern Instruments Ltd., Worcestershire, UK).
  • Mg 2+ The physical nature of the solidified state at high Mg 2+ ratios is non- fluid, but softer and more gel- like than the hard Ca 2+ precipitates, reflecting perhaps an intermediate state of desolvation relative to fluid coacervates and solids.
  • the distinct physical nature and solubility profile of the Mg 2+ complexes are likely consequences of the smaller radius, higher charge density, and smaller coordination number of Mg 2+ ions compared to Ca 2+ ions.
  • Mg 2+ tends to coordinate single bulky ligands, like phosphate, because multiple ligands won't fit around the small ion. As a consequence much of its solvation sphere is retained.

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PCT/US2010/043009 2009-07-23 2010-07-23 Adhesive complex coacervates and methods of making and using thereof Ceased WO2011011658A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2012521803A JP5928825B2 (ja) 2009-07-23 2010-07-23 接着複合コアセルベートならびにそれを作製および使用する方法
CN2010800383973A CN102548581A (zh) 2009-07-23 2010-07-23 粘合复合物凝聚层及其制备和使用方法
AU2010275504A AU2010275504A1 (en) 2009-07-23 2010-07-23 Adhesive complex coacervates and methods of making and using thereof
EP10802933.1A EP2456466B1 (en) 2009-07-23 2010-07-23 Adhesive complex coacervates and methods of making and using thereof
CA2768501A CA2768501A1 (en) 2009-07-23 2010-07-23 Adhesive complex coacervates and methods of making and using thereof

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US12/508,280 US8283384B2 (en) 2008-01-24 2009-07-23 Adhesive complex coacervates and methods of making and using thereof

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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US20180272027A1 (en) 2018-09-27
AU2010275504A1 (en) 2012-02-02
US9913926B2 (en) 2018-03-13
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US20130189313A1 (en) 2013-07-25
US20100120923A1 (en) 2010-05-13
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US10517987B2 (en) 2019-12-31
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CA2768501A1 (en) 2011-01-27
US8283384B2 (en) 2012-10-09

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