AU2011325961A1 - Simple adhesive coacervates and methods of making and using thereof - Google Patents
Simple adhesive coacervates and methods of making and using thereof Download PDFInfo
- Publication number
- AU2011325961A1 AU2011325961A1 AU2011325961A AU2011325961A AU2011325961A1 AU 2011325961 A1 AU2011325961 A1 AU 2011325961A1 AU 2011325961 A AU2011325961 A AU 2011325961A AU 2011325961 A AU2011325961 A AU 2011325961A AU 2011325961 A1 AU2011325961 A1 AU 2011325961A1
- Authority
- AU
- Australia
- Prior art keywords
- adhesive
- group
- substrate
- polycation
- coacervate
- 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
- 239000000853 adhesive Substances 0.000 title claims abstract description 217
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 217
- 238000000034 method Methods 0.000 title claims description 51
- 238000004132 cross linking Methods 0.000 claims abstract description 65
- 229920000447 polyanionic polymer Polymers 0.000 claims abstract description 61
- 229920000867 polyelectrolyte Polymers 0.000 claims abstract description 57
- 239000000758 substrate Substances 0.000 claims description 62
- 229920000642 polymer Polymers 0.000 claims description 57
- 239000000178 monomer Substances 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 239000004971 Cross linker Substances 0.000 claims description 35
- 210000000988 bone and bone Anatomy 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000003277 amino group Chemical group 0.000 claims description 31
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims description 13
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- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 claims description 9
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- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 5
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- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
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- 239000003922 charged colloid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
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- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Chemical class SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000003479 dental cement Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 229940095079 dicalcium phosphate anhydrous Drugs 0.000 description 1
- RBLGLDWTCZMLRW-UHFFFAOYSA-K dicalcium phosphate dihydrate Substances O.O.[Ca+2].[Ca+2].[O-]P([O-])([O-])=O RBLGLDWTCZMLRW-UHFFFAOYSA-K 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
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- 239000002158 endotoxin Substances 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960004887 ferric hydroxide Drugs 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
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- 230000023597 hemostasis Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical group CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- 229920002674 hyaluronan Polymers 0.000 description 1
- 229960003160 hyaluronic acid Drugs 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
- IEECXTSVVFWGSE-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Fe+3] IEECXTSVVFWGSE-UHFFFAOYSA-M 0.000 description 1
- 229910021506 iron(II) hydroxide Inorganic materials 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 235000021239 milk protein Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000150 monocalcium phosphate Inorganic materials 0.000 description 1
- 235000019691 monocalcium phosphate Nutrition 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000011858 nanopowder Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 150000002843 nonmetals Chemical class 0.000 description 1
- 229910000392 octacalcium phosphate Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000003239 periodontal effect Effects 0.000 description 1
- 125000002081 peroxide group Chemical group 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 229940045919 sodium polymetaphosphate Drugs 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YIGWVOWKHUSYER-UHFFFAOYSA-F tetracalcium;hydrogen phosphate;diphosphate Chemical compound [Ca+2].[Ca+2].[Ca+2].[Ca+2].OP([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O YIGWVOWKHUSYER-UHFFFAOYSA-F 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 102000003601 transglutaminase Human genes 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
Classifications
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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
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/06—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
-
- 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
-
- 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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/08—Materials for coatings
- A61L31/10—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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/16—Biologically active materials, e.g. therapeutic substances
-
- 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
- C09J143/00—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 containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Adhesives based on derivatives of such polymers
- C09J143/02—Homopolymers or copolymers of monomers containing phosphorus
-
- 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
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/418—Agents promoting blood coagulation, blood-clotting agents, embolising agents
-
- 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
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/18—Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Surgery (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Materials For Medical Uses (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Dental Preparations (AREA)
- Surgical Instruments (AREA)
- Adhesive Tapes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41283410P | 2010-11-12 | 2010-11-12 | |
| US61/412,834 | 2010-11-12 | ||
| PCT/US2011/060500 WO2012065148A2 (en) | 2010-11-12 | 2011-11-12 | Simple adhesive coacervates and methods of making and using thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2011325961A1 true AU2011325961A1 (en) | 2013-03-28 |
Family
ID=45094250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2011325961A Abandoned AU2011325961A1 (en) | 2010-11-12 | 2011-11-12 | Simple adhesive coacervates and methods of making and using thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US9173971B2 (https=) |
| EP (1) | EP2637708A2 (https=) |
| JP (1) | JP2014502296A (https=) |
| CN (1) | CN103179992A (https=) |
| AU (1) | AU2011325961A1 (https=) |
| CA (1) | CA2812599A1 (https=) |
| WO (1) | WO2012065148A2 (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5530934B2 (ja) | 2008-01-24 | 2014-06-25 | ユニバーシティ オブ ユタ リサーチ ファンデーション | 接着複合コアセルベートならびにその作製および使用方法 |
| US8283384B2 (en) | 2008-01-24 | 2012-10-09 | University Of Utah Research Foundation | Adhesive complex coacervates and methods of making and using thereof |
| US20110287067A1 (en) | 2010-05-24 | 2011-11-24 | University Of Utah Research Foundation | Reinforced adhesive complex coacervates and methods of making and using thereof |
| CN103179992A (zh) | 2010-11-12 | 2013-06-26 | 犹他大学研究基金会 | 简单的粘合剂凝聚层以及制备和使用方法 |
| WO2013134269A2 (en) * | 2012-03-06 | 2013-09-12 | Kci Licensing, Inc. | New compositions, the preparation and use thereof |
| EP2953992B1 (en) | 2013-02-06 | 2021-11-24 | 3M Innovative Properties Company | Polymers, preparation and use thereof |
| CN103242762A (zh) * | 2013-05-31 | 2013-08-14 | 苏州华周胶带有限公司 | 一种以环氧薄膜为基材的胶带的制造方法 |
| CA2932645A1 (en) * | 2013-12-10 | 2015-06-18 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods for adhering tissue surfaces and materials and biomedical uses thereof |
| US9814778B2 (en) | 2014-03-06 | 2017-11-14 | The University Of Toledo | Ionically crosslinked polyelectrolytes as underwater adhesives as controlled release vehicles |
| US9913927B2 (en) * | 2014-07-14 | 2018-03-13 | University Of Utah Research Foundation | In situ solidifying complex coacervates and methods of making and using thereof |
| CN105770983B (zh) * | 2016-03-14 | 2019-02-19 | 武汉纺织大学 | 一种透明质酸生物粘合剂的制备方法 |
| KR20180124132A (ko) | 2016-03-29 | 2018-11-20 | 세이프화이트 인코포레이티드 | 치아 및 치아 구성요소의 미백을 위한 고분자 전해질 치과용 접착제 |
| CN106798952B (zh) * | 2017-02-13 | 2019-12-10 | 先健科技(深圳)有限公司 | 可吸收铁基骨折内固定材料 |
| TW201918244A (zh) * | 2017-09-29 | 2019-05-16 | 美商安潔公司 | 聚電解質的牙科塗料 |
| EP3691696A4 (en) * | 2017-10-02 | 2021-06-30 | Aleo BME, Inc. | Aqueous tissue adhesives |
| WO2019084548A1 (en) * | 2017-10-27 | 2019-05-02 | University Of Utah Research Foundation | COMPLEX LIQUID IN SITU SOLIDIFICATION COASTALITIES FOR LOCAL ADMINISTRATION OF ANTI-ANGIOGENIC AGENTS OR CHEMOTHERAPEUTIC AGENTS |
| AU2019212513B2 (en) | 2018-01-26 | 2024-10-31 | Fluidx Medical Technology, Llc | Apparatus and method of using in situ solidifying complex coacervates for vascular occlusion |
| CN108186371B (zh) * | 2018-02-05 | 2020-09-22 | 上海御齿台医疗科技有限公司 | 安全种植牙用粘合剂及其制备方法 |
| CN109453144A (zh) * | 2019-01-04 | 2019-03-12 | 巴斯特医药科技（常州）有限公司 | 具有可膨润性低密度网传输槽的长效控释复合膜及其制法 |
| DE102019109150A1 (de) * | 2019-04-08 | 2020-10-08 | Mühlbauer Technology Gmbh | Remineralisierendes Dentalmaterial |
| DE102020124372A1 (de) * | 2020-09-18 | 2022-03-24 | Carl Zeiss Meditec Ag | Gewebekleber zur Anwendung in einem Behandlungsverfahren, bei welchem einem menschlichen oder tierischen Patienten ein ophthalmologisches Implantat implantiert wird, und ophthalmologisches Implantationssystem |
| CN114533944A (zh) * | 2022-03-01 | 2022-05-27 | 袁淑惠 | 一种基于天然化合物的弹性体组织密封胶及其制备方法 |
| FR3135475B1 (fr) | 2022-05-12 | 2025-03-21 | Saint Gobain Adfors | Revêtement mural préencollé avec une composition adhésive latente activable à l’eau |
| EP4299680A1 (en) | 2022-06-29 | 2024-01-03 | Saint-Gobain Weber France | Quick setting aqueous composition comprising polyelectrolyte coacervates and polyphenols |
| CN114939192B (zh) * | 2022-07-01 | 2023-05-12 | 郑州大学第一附属医院 | 一种巩膜钉用水凝胶及其制备方法和应用 |
| EP4634448A1 (fr) | 2022-12-16 | 2025-10-22 | Saint-Gobain Adfors | Textile lié par un liant à base de polyélectrolytes à polarités de charge opposees |
| FR3145939B1 (fr) | 2023-02-21 | 2025-03-21 | Saint Gobain Isover | Amélioration de l’adhésion entre l’isolant et l’enduit dans des systèmes d’isolation thermique par l’extérieur de bâtiments |
Family Cites Families (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3456460A (en) | 1967-04-11 | 1969-07-22 | Singer Co | Cylinder and dial knitting machine |
| US3458460A (en) | 1967-11-27 | 1969-07-29 | Hooker Chemical Corp | Unsaturated polyesters cross-linked by diels-alder reaction |
| US3950296A (en) | 1972-04-28 | 1976-04-13 | The Dow Chemical Company | Reversible coacervation of anion-containing aqueous disperse systems with amphoteric polyelectrolytes |
| US3947396A (en) | 1972-04-28 | 1976-03-30 | The Dow Chemical Company | Coacervation of anion-containing aqueous disperse systems with amphoteric polyelectrolytes |
| US4767463A (en) | 1987-04-15 | 1988-08-30 | Union Carbide Corporation | Glycosaminoglycan and cationic polymer combinations |
| US4913743A (en) | 1987-04-15 | 1990-04-03 | Biomatrix, Inc. | Processes for managing keratinous material using glycosaminoglycan and cationic polymer combinations |
| US5529914A (en) | 1990-10-15 | 1996-06-25 | The Board Of Regents The Univeristy Of Texas System | Gels for encapsulation of biological materials |
| TW328535B (en) | 1993-07-02 | 1998-03-21 | Novartis Ag | Functional photoinitiators and their manufacture |
| WO1995003789A1 (en) * | 1993-07-28 | 1995-02-09 | The Johns Hopkins University School Of Medicine | Controlled release of pharmaceutically active substances from coacervate microcapsules |
| WO1995006056A1 (en) | 1993-08-20 | 1995-03-02 | University Of Medicine & Dentistry Of New Jersey | Bridged polycationic polymer-oligonucleotide conjugates and methods for preparing same |
| JPH11505505A (ja) * | 1994-06-27 | 1999-05-21 | ザ・ジョンズ・ホプキンス・ユニバーシティー | ターゲッティングされた遺伝子輸送システム |
| JP2000514440A (ja) * | 1996-07-09 | 2000-10-31 | ザ ジョーンズ ホプキンス ユニバーシティー | 遺伝子輸送システム |
| JP2002515932A (ja) * | 1997-04-18 | 2002-05-28 | カリフォルニア インスティチュート オブ テクノロジー | 多機能性ポリマー性組織コーティング |
| CA2303268A1 (en) * | 1997-06-13 | 1998-12-17 | Scott Walsh | Therapeutic nanospheres |
| DE19810965A1 (de) | 1998-03-13 | 1999-09-16 | Aventis Res & Tech Gmbh & Co | Nanopartikel, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US6428978B1 (en) | 1998-05-08 | 2002-08-06 | Cohesion Technologies, Inc. | Methods for the production of gelatin and full-length triple helical collagen in recombinant cells |
| ATE269114T1 (de) * | 1998-11-20 | 2004-07-15 | Univ Connecticut | Verfahren und vorrichtung zur steuerung der gewebeimplantat-interaktionen |
| JP2002535046A (ja) | 1999-01-22 | 2002-10-22 | セント・ジュード・メディカル・インコーポレーテッド | 基質／接着剤成分複合体 |
| US6312725B1 (en) | 1999-04-16 | 2001-11-06 | Cohesion Technologies, Inc. | Rapid gelling biocompatible polymer composition |
| US6916488B1 (en) | 1999-11-05 | 2005-07-12 | Biocure, Inc. | Amphiphilic polymeric vesicles |
| US20020006886A1 (en) | 1999-11-19 | 2002-01-17 | Peter William Beerse | Personal care articles comprising cationic polymer coacervate compositions |
| JP5460939B2 (ja) | 2000-03-13 | 2014-04-02 | バイオコンパティブルズ ユーケー リミテッド | ヒドロゲル生物医学用製品 |
| US20040013738A1 (en) | 2000-08-02 | 2004-01-22 | Andreas Voigt | Encapsulation of liquid template particles |
| US6488870B1 (en) | 2000-11-27 | 2002-12-03 | Xerox Corporation | Encapsulation process |
| MXPA03007665A (es) | 2001-02-26 | 2004-03-16 | Univ Duke | Polimeros dendriticos novedosos y sus usos biomedicos. |
| US6568398B2 (en) | 2001-03-07 | 2003-05-27 | Edgar C. Cohen | Method for hemostasis |
| US6562361B2 (en) | 2001-05-02 | 2003-05-13 | 3M Innovative Properties Company | Pheromone immobilized in stable hydrogel microbeads |
| FR2824756B1 (fr) | 2001-05-16 | 2005-07-08 | Mainelab | Microcapsules a base de proteines vegetales |
| CA2449964A1 (en) | 2001-06-07 | 2002-12-19 | Surmodics, Inc. | Crosslinkable macromers |
| US6559233B2 (en) | 2001-07-13 | 2003-05-06 | Rhodia Chimie | Composition comprising a copolymer at least two charged blocks and type of opposite charge |
| US7204997B2 (en) | 2002-01-29 | 2007-04-17 | Supratek Pharma Inc. | Responsive microgel and methods related thereto |
| CA2476777A1 (en) | 2002-03-11 | 2003-09-25 | First Water Limited | Absorbent hydrogels |
| JP4058283B2 (ja) | 2002-03-22 | 2008-03-05 | 株式会社リコー | 振動検出装置 |
| US7060798B2 (en) | 2002-05-13 | 2006-06-13 | State Of Oregon Acting By And Through The Oregon State Board Of Higher Education On Behalf Of Oregon State University | Modified protein adhesives and lignocellulosic composites made from the adhesives |
| US6958848B2 (en) | 2002-05-23 | 2005-10-25 | E Ink Corporation | Capsules, materials for use therein and electrophoretic media and displays containing such capsules |
| US6800663B2 (en) | 2002-10-18 | 2004-10-05 | Alkermes Controlled Therapeutics Inc. Ii, | Crosslinked hydrogel copolymers |
| US8105652B2 (en) | 2002-10-24 | 2012-01-31 | Massachusetts Institute Of Technology | Methods of making decomposable thin films of polyelectrolytes and uses thereof |
| CN1446590A (zh) | 2003-01-21 | 2003-10-08 | 华东理工大学 | 新型聚肽/磷酸钙复合骨水泥 |
| DE10334753A1 (de) | 2003-07-30 | 2005-03-10 | Constr Res & Tech Gmbh | Selbstvernetzende hochmolekulare Polyurethan-Dispersion |
| WO2005019421A2 (en) * | 2003-08-11 | 2005-03-03 | University Of Utah Research Foundation | Crosslinking within coordination complexes |
| US7544770B2 (en) | 2003-08-29 | 2009-06-09 | Louisiana Tech Foundation, Inc. | Multilayer films, coatings, and microcapsules comprising polypeptides |
| EP1518568B1 (en) | 2003-09-25 | 2009-05-27 | Wageningen Universiteit, Agrotechnologie en Voedingswetenschappen | Complex coacervate core micelles as anti-fouling agents |
| US7608674B2 (en) | 2003-11-03 | 2009-10-27 | Ilypsa, Inc. | Pharmaceutical compositions comprising cross-linked small molecule amine polymers |
| WO2005065079A2 (en) | 2003-11-10 | 2005-07-21 | Angiotech International Ag | Medical implants and fibrosis-inducing agents |
| US7780873B2 (en) | 2004-02-23 | 2010-08-24 | Texas A&M University System | Bioactive complexes compositions and methods of use thereof |
| WO2007024972A2 (en) | 2005-08-22 | 2007-03-01 | Quick-Med Technologies, Inc. | Non-leaching absorbent wound dressing |
| US7854924B2 (en) | 2004-03-30 | 2010-12-21 | Relypsa, Inc. | Methods and compositions for treatment of ion imbalances |
| CN104174071A (zh) | 2004-04-28 | 2014-12-03 | 安希奥设备国际有限责任公司 | 用于形成交联生物材料的组合物和系统及关联的制备方法与用途 |
| US8728526B2 (en) | 2004-08-19 | 2014-05-20 | The United States of America, Represented by Secretary of Department of Health and Human Services, NIH | Coacervate microparticles useful for the sustained release administration of therapeutic agents |
| US20060039950A1 (en) | 2004-08-23 | 2006-02-23 | Zhengrong Zhou | Multi-functional biocompatible coatings for intravascular devices |
| US20060116682A1 (en) | 2004-11-18 | 2006-06-01 | Longo Marc N | Surgical implant and methods of making and using the same |
| US7795359B2 (en) | 2005-03-04 | 2010-09-14 | Novartis Ag | Continuous process for production of polymeric materials |
| WO2006130709A2 (en) | 2005-06-01 | 2006-12-07 | Rhodia Inc. | Coacervate systems having soil anti-adhesion and anti-deposition properties on hydrophilic surfaces |
| AU2006287306A1 (en) | 2005-09-09 | 2007-03-15 | Duke University | Tissue engineering methods and compositions |
| CA2635374C (en) | 2006-01-11 | 2015-12-08 | Hyperbranch Medical Technology, Inc. | Crosslinked gels comprising polyalkyleneimines, and their uses as medical devices |
| US9198981B2 (en) | 2006-02-01 | 2015-12-01 | The University Of Kentucky | Modulation of angiogenesis |
| CN101405037A (zh) | 2006-02-27 | 2009-04-08 | 新加坡科技研究局 | 可固化骨粘固剂 |
| US7622533B2 (en) | 2006-08-04 | 2009-11-24 | Nerites Corporation | Biomimetic compounds and synthetic methods therefor |
| DE102007015698B4 (de) | 2007-03-27 | 2009-05-14 | Innotere Gmbh | Implantatmaterial auf Basis eines Polymersystems und dessen Verwendung sowie Applikationsset |
| JP2009084224A (ja) | 2007-09-28 | 2009-04-23 | Fujifilm Corp | マイクロカプセル及びその製造方法 |
| WO2009085952A1 (en) | 2007-12-20 | 2009-07-09 | Brookwood Pharmaceuticals, Inc. | Process for preparing microparticles having a low residual solvent volume |
| JP5530934B2 (ja) | 2008-01-24 | 2014-06-25 | ユニバーシティ オブ ユタ リサーチ ファンデーション | 接着複合コアセルベートならびにその作製および使用方法 |
| US8283384B2 (en) * | 2008-01-24 | 2012-10-09 | University Of Utah Research Foundation | Adhesive complex coacervates and methods of making and using thereof |
| BRPI0911004B1 (pt) | 2008-07-18 | 2022-05-17 | Quick-Med Technologies, Inc | Método de preparação de um artigo antimicrobiano e artigo antimicrobiano |
| WO2010021930A1 (en) | 2008-08-16 | 2010-02-25 | Synedgen, Inc. | Prevention and treatment of mrsa infections with chitosan-derivatives |
| JP2009084292A (ja) | 2008-11-14 | 2009-04-23 | Cell-Medicine Inc | 免疫アジュバント |
| EP2454367B1 (en) | 2009-07-17 | 2013-10-16 | The Texas A&M University System | Designer collagens and uses thereof |
| DE102009033616A1 (de) | 2009-07-17 | 2011-01-20 | Karl Heinz Linnig Gmbh & Co. Kg | Kühlvorrichtung, insbesondere Brennkraftmaschinenkühlvorrichtung, mit einer Sekundärantriebsmaschine |
| CA3004707C (en) | 2009-09-02 | 2022-05-31 | Synedgen Inc. | Methods and compositions for disrupting biofilm utilizing chitosan-derivative compounds |
| JP2013521342A (ja) | 2010-02-26 | 2013-06-10 | ユニバーシティ・オブ・ユタ・リサーチ・ファウンデイション | 静電会合したブロック共重合体から生成される接着複合コアセルベート並びにその作製及び使用方法 |
| US20110287067A1 (en) | 2010-05-24 | 2011-11-24 | University Of Utah Research Foundation | Reinforced adhesive complex coacervates and methods of making and using thereof |
| CN103179992A (zh) * | 2010-11-12 | 2013-06-26 | 犹他大学研究基金会 | 简单的粘合剂凝聚层以及制备和使用方法 |
| IN2014CN03524A (https=) | 2011-11-13 | 2015-10-09 | Suneris Inc |
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| US20120177918A1 (en) | 2012-07-12 |
| US9421300B2 (en) | 2016-08-23 |
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| CN103179992A (zh) | 2013-06-26 |
| US9173971B2 (en) | 2015-11-03 |
| WO2012065148A3 (en) | 2012-07-05 |
| CA2812599A1 (en) | 2012-05-18 |
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