CA2799818A1 - Reinforced adhesive complex coacervates and methods of making and using thereof - Google Patents
Reinforced adhesive complex coacervates and methods of making and using thereof Download PDFInfo
- Publication number
- CA2799818A1 CA2799818A1 CA2799818A CA2799818A CA2799818A1 CA 2799818 A1 CA2799818 A1 CA 2799818A1 CA 2799818 A CA2799818 A CA 2799818A CA 2799818 A CA2799818 A CA 2799818A CA 2799818 A1 CA2799818 A1 CA 2799818A1
- Authority
- CA
- Canada
- Prior art keywords
- adhesive complex
- complex coacervate
- group
- coacervate
- polycation
- 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 223
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 223
- 238000000034 method Methods 0.000 title claims description 41
- 229920000447 polyanionic polymer Polymers 0.000 claims abstract description 122
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
- 230000003014 reinforcing effect Effects 0.000 claims abstract description 36
- 239000000178 monomer Substances 0.000 claims description 81
- -1 guanidinyl group Chemical group 0.000 claims description 77
- 229920000642 polymer Polymers 0.000 claims description 56
- 238000004132 cross linking Methods 0.000 claims description 54
- 239000003999 initiator Substances 0.000 claims description 53
- 239000000945 filler Substances 0.000 claims description 52
- 229920000768 polyamine Polymers 0.000 claims description 39
- 210000000988 bone and bone Anatomy 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000000758 substrate Substances 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 26
- 229920000388 Polyphosphate Polymers 0.000 claims description 25
- 239000001205 polyphosphate Substances 0.000 claims description 25
- 235000011176 polyphosphates Nutrition 0.000 claims description 25
- 230000001590 oxidative effect Effects 0.000 claims description 24
- 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 24
- 125000003277 amino group Chemical group 0.000 claims description 23
- 239000000693 micelle Substances 0.000 claims description 22
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 21
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 20
- 239000001506 calcium phosphate Substances 0.000 claims description 20
- 230000000269 nucleophilic effect Effects 0.000 claims description 20
- 239000007800 oxidant agent Substances 0.000 claims description 18
- 239000002245 particle Substances 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 18
- 229910019142 PO4 Inorganic materials 0.000 claims description 17
- 208000010392 Bone Fractures Diseases 0.000 claims description 16
- 150000001768 cations Chemical class 0.000 claims description 16
- 210000001519 tissue Anatomy 0.000 claims description 16
- 239000002202 Polyethylene glycol Substances 0.000 claims description 15
- 239000012867 bioactive agent Substances 0.000 claims description 15
- 229910000389 calcium phosphate Inorganic materials 0.000 claims description 15
- 235000011010 calcium phosphates Nutrition 0.000 claims description 15
- 239000012634 fragment Substances 0.000 claims description 15
- 239000010452 phosphate Substances 0.000 claims description 15
- 229920001223 polyethylene glycol Polymers 0.000 claims description 15
- 108090000623 proteins and genes Proteins 0.000 claims description 15
- 125000000129 anionic group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052588 hydroxylapatite Inorganic materials 0.000 claims description 14
- 239000002086 nanomaterial Substances 0.000 claims description 14
- 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 14
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 14
- 108020004707 nucleic acids Proteins 0.000 claims description 13
- 102000039446 nucleic acids Human genes 0.000 claims description 13
- 150000007523 nucleic acids Chemical class 0.000 claims description 13
- 125000002091 cationic group Chemical group 0.000 claims description 12
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 11
- 239000002502 liposome Substances 0.000 claims description 11
- 102000004169 proteins and genes Human genes 0.000 claims description 11
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000004971 Cross linker Substances 0.000 claims description 9
- 208000027418 Wounds and injury Diseases 0.000 claims description 9
- 229920005615 natural polymer Polymers 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229910001428 transition metal ion Inorganic materials 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 150000004676 glycans Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000011859 microparticle Substances 0.000 claims description 6
- 229920001282 polysaccharide Polymers 0.000 claims description 6
- 239000005017 polysaccharide Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 210000004872 soft tissue Anatomy 0.000 claims description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 6
- 238000001356 surgical procedure Methods 0.000 claims description 6
- 239000002407 tissue scaffold Substances 0.000 claims description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 5
- 206010052428 Wound Diseases 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 239000012528 membrane Substances 0.000 claims description 5
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 229920001059 synthetic polymer Polymers 0.000 claims description 5
- 229910000391 tricalcium phosphate Inorganic materials 0.000 claims description 5
- 102000007350 Bone Morphogenetic Proteins Human genes 0.000 claims description 4
- 108010007726 Bone Morphogenetic Proteins Proteins 0.000 claims description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 4
- 108010010803 Gelatin Proteins 0.000 claims description 4
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 claims description 4
- 229940112869 bone morphogenetic protein Drugs 0.000 claims description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 claims description 4
- 229920000159 gelatin Polymers 0.000 claims description 4
- 239000008273 gelatin Substances 0.000 claims description 4
- 235000019322 gelatine Nutrition 0.000 claims description 4
- 235000011852 gelatine desserts Nutrition 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000002105 nanoparticle Substances 0.000 claims description 4
- 150000002978 peroxides Chemical class 0.000 claims description 4
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 208000034693 Laceration Diseases 0.000 claims description 3
- 102000007056 Recombinant Fusion Proteins Human genes 0.000 claims description 3
- 108010008281 Recombinant Fusion Proteins Proteins 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229940088710 antibiotic agent Drugs 0.000 claims description 3
- 230000017531 blood circulation Effects 0.000 claims description 3
- 125000004386 diacrylate group Chemical group 0.000 claims description 3
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 3
- 239000003102 growth factor Substances 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 229940124641 pain reliever Drugs 0.000 claims description 3
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 229940078499 tricalcium phosphate Drugs 0.000 claims description 3
- 229920001567 vinyl ester resin Chemical group 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- VALXVSHDOMUUIC-UHFFFAOYSA-N 2-methylprop-2-enoic acid;phosphoric acid Chemical compound OP(O)(O)=O.CC(=C)C(O)=O VALXVSHDOMUUIC-UHFFFAOYSA-N 0.000 claims description 2
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 claims description 2
- 208000010412 Glaucoma Diseases 0.000 claims description 2
- 210000004204 blood vessel Anatomy 0.000 claims description 2
- 230000005754 cellular signaling Effects 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 239000002532 enzyme inhibitor Substances 0.000 claims description 2
- 125000003916 ethylene diamine group Chemical group 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- 229940088597 hormone Drugs 0.000 claims description 2
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims description 2
- WDHYRUBXLGOLKR-UHFFFAOYSA-N phosphoric acid;prop-2-enoic acid Chemical compound OC(=O)C=C.OP(O)(O)=O WDHYRUBXLGOLKR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003505 polymerization initiator Substances 0.000 claims description 2
- 150000003180 prostaglandins Chemical class 0.000 claims description 2
- 239000000018 receptor agonist Substances 0.000 claims description 2
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- 239000002464 receptor antagonist Substances 0.000 claims description 2
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- 239000002151 riboflavin Substances 0.000 claims description 2
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- 229930187593 rose bengal Natural products 0.000 claims description 2
- 229940081623 rose bengal Drugs 0.000 claims description 2
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- 208000002847 Surgical Wound Diseases 0.000 claims 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
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- 229910052761 rare earth metal Inorganic materials 0.000 claims 1
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- 239000012744 reinforcing agent Substances 0.000 claims 1
- AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 0.000 claims 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
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- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
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- LQAZPMXASFNKCD-UHFFFAOYSA-M potassium;dodecane-1-sulfonate Chemical compound [K+].CCCCCCCCCCCCS([O-])(=O)=O LQAZPMXASFNKCD-UHFFFAOYSA-M 0.000 description 1
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- 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
- DLSMLZRPNPCXGY-UHFFFAOYSA-N tert-butylperoxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOOC(C)(C)C DLSMLZRPNPCXGY-UHFFFAOYSA-N 0.000 description 1
- YEAUATLBSVJFOY-UHFFFAOYSA-N tetraantimony hexaoxide Chemical compound O1[Sb](O2)O[Sb]3O[Sb]1O[Sb]2O3 YEAUATLBSVJFOY-UHFFFAOYSA-N 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
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- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- UONOETXJSWQNOL-UHFFFAOYSA-N tungsten carbide Chemical compound [W+]#[C-] UONOETXJSWQNOL-UHFFFAOYSA-N 0.000 description 1
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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
- A61L24/046—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
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| CA2799818A1 (en) | 2010-05-24 | 2011-12-01 | University Of Utah Research Foundation | Reinforced adhesive complex coacervates and methods of making and using thereof |
| EP2637708A2 (en) | 2010-11-12 | 2013-09-18 | University of Utah Research Foundation | Simple adhesive coacervates and methods of making and using thereof |
| WO2012158527A2 (en) | 2011-05-13 | 2012-11-22 | Howmedica Osteonics | Organophosphorous & multivalent metal compound compositions & methods |
| CA2840593A1 (en) * | 2011-06-28 | 2013-01-03 | University Of Utah Research Foundation | Adhesive complex coacervates and methods of making and using thereof |
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| KR102218427B1 (ko) | 2017-09-20 | 2021-02-22 | 차의과학대학교 산학협력단 | 단백질 약물을 포함하는 코아세르베이트 조성물 및 이를 포함하는 창상 치료제 |
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| CA3084142C (en) * | 2017-12-31 | 2024-03-12 | Purdue Research Foundation | Adhesives |
| JP7410876B2 (ja) | 2018-01-26 | 2024-01-10 | フルイデックス メディカル テクノロジー，リミティッド ライアビリティ カンパニー | 血管閉塞のためにその場凝固複合コアセルベートを使用する装置及び方法 |
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| EP4054548A4 (en) * | 2019-11-04 | 2023-12-13 | RevBio, Inc. | Adhesive compositions comprising therapeutics |
| CN113368080B (zh) * | 2020-02-25 | 2023-11-17 | 香港中文大学 | 稳定的、生物粘附的、扩散限制性团聚体 |
| CN113827772B (zh) * | 2020-06-23 | 2022-08-09 | 中国科学院上海硅酸盐研究所 | 一种具有氧化还原响应释药功能的生物抗氧化纳米涂层及其制备方法与应用 |
| 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 |
| CN114763457B (zh) * | 2021-01-15 | 2023-06-16 | 天津大学 | 适用于多种恶劣环境的高强长效的黏合剂及其制备方法和应用 |
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| US20240391775A1 (en) * | 2021-09-27 | 2024-11-28 | Junji Sakamoto | Polyphosphate materials |
| CN118804949A (zh) * | 2021-11-10 | 2024-10-18 | 马萨诸塞大学 | 液体复合凝聚层、衍生自其的制品以及用于制造其的方法 |
| CN114225109B (zh) * | 2021-12-22 | 2022-08-23 | 上海交通大学 | 一种人工神经鞘水凝胶修复系统及其制备方法和应用 |
| FR3135475B1 (fr) | 2022-05-12 | 2025-03-21 | Saint Gobain Adfors | Revêtement mural préencollé avec une composition adhésive latente activable à l’eau |
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| EP4299680A1 (en) | 2022-06-29 | 2024-01-03 | Saint-Gobain Weber France | Quick setting aqueous composition comprising polyelectrolyte coacervates and polyphenols |
| CN117080440A (zh) * | 2022-11-03 | 2023-11-17 | 中国科学院宁波材料技术与工程研究所 | 一种复合粘结剂、锂离子电池正极极片及锂离子电池 |
| US20260210011A1 (en) | 2022-12-16 | 2026-07-23 | Saint-Gobain Adfors | Textile bonded by a binder based on polyelectrolytes having opposite charge polarities |
| 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 |
| CN116426168B (zh) * | 2023-03-13 | 2024-05-28 | 北京航空航天大学 | 一种基于水凝胶的超浸润性对多种基底进行涂层修饰的制备方法 |
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-
2011
- 2011-05-24 CA CA2799818A patent/CA2799818A1/en not_active Abandoned
- 2011-05-24 WO PCT/US2011/037697 patent/WO2011149907A1/en not_active Ceased
- 2011-05-24 US US13/114,397 patent/US20110287067A1/en not_active Abandoned
- 2011-05-24 JP JP2013512145A patent/JP2013526393A/ja active Pending
- 2011-05-24 CN CN2011800249818A patent/CN103025360A/zh active Pending
- 2011-05-24 EP EP11727837.4A patent/EP2575906B1/en active Active
-
2016
- 2016-04-18 US US15/131,583 patent/US9867899B2/en active Active
-
2017
- 2017-12-06 US US15/833,157 patent/US10653813B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2575906A1 (en) | 2013-04-10 |
| US20180099070A1 (en) | 2018-04-12 |
| EP2575906B1 (en) | 2014-12-10 |
| JP2013526393A (ja) | 2013-06-24 |
| WO2011149907A1 (en) | 2011-12-01 |
| US9867899B2 (en) | 2018-01-16 |
| US20160250375A1 (en) | 2016-09-01 |
| US20110287067A1 (en) | 2011-11-24 |
| US10653813B2 (en) | 2020-05-19 |
| CN103025360A (zh) | 2013-04-03 |
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