JP7019884B2 - 外科用接着剤 - Google Patents
外科用接着剤 Download PDFInfo
- Publication number
- JP7019884B2 JP7019884B2 JP2017560619A JP2017560619A JP7019884B2 JP 7019884 B2 JP7019884 B2 JP 7019884B2 JP 2017560619 A JP2017560619 A JP 2017560619A JP 2017560619 A JP2017560619 A JP 2017560619A JP 7019884 B2 JP7019884 B2 JP 7019884B2
- Authority
- JP
- Japan
- Prior art keywords
- composition according
- composition
- methacrylate
- acrylate
- acrylic acid
- 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.)
- Active
Links
- 239000003894 surgical glue Substances 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims description 69
- 239000000178 monomer Substances 0.000 claims description 47
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 29
- -1 carbamate ester Chemical class 0.000 claims description 21
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 20
- 239000000853 adhesive Substances 0.000 claims description 17
- 230000001070 adhesive effect Effects 0.000 claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- 239000003431 cross linking reagent Substances 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 239000003999 initiator Substances 0.000 claims description 8
- 230000000977 initiatory effect Effects 0.000 claims description 7
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 4
- 229930185605 Bisphenol Natural products 0.000 claims description 4
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- FEUFEGJTJIHPOF-UHFFFAOYSA-N 2-butyl acrylic acid Chemical group CCCCC(=C)C(O)=O FEUFEGJTJIHPOF-UHFFFAOYSA-N 0.000 claims description 3
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims description 3
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- 125000004386 diacrylate group Chemical group 0.000 claims description 3
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 claims description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- JNNKWUPPLJTSSJ-UHFFFAOYSA-N chloromethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCl JNNKWUPPLJTSSJ-UHFFFAOYSA-N 0.000 claims description 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 2
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 claims description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 2
- CXOYJPWMGYDJNW-UHFFFAOYSA-N naphthalen-2-yl 2-methylprop-2-enoate Chemical compound C1=CC=CC2=CC(OC(=O)C(=C)C)=CC=C21 CXOYJPWMGYDJNW-UHFFFAOYSA-N 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000003014 reinforcing effect Effects 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 claims description 2
- CNLVUQQHXLTOTC-UHFFFAOYSA-N (2,4,6-tribromophenyl) prop-2-enoate Chemical compound BrC1=CC(Br)=C(OC(=O)C=C)C(Br)=C1 CNLVUQQHXLTOTC-UHFFFAOYSA-N 0.000 claims 1
- FJDAOINLDVUIKL-UHFFFAOYSA-N 1-bromoethyl prop-2-enoate Chemical compound CC(Br)OC(=O)C=C FJDAOINLDVUIKL-UHFFFAOYSA-N 0.000 claims 1
- AOUSBQVEVZBMNI-UHFFFAOYSA-N 2-bromoethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCBr AOUSBQVEVZBMNI-UHFFFAOYSA-N 0.000 claims 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical group OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 description 51
- 229920001651 Cyanoacrylate Polymers 0.000 description 4
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 239000003106 tissue adhesive Substances 0.000 description 4
- 230000002439 hemostatic effect Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000023597 hemostasis Effects 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 210000003516 pericardium Anatomy 0.000 description 2
- MUZDXNQOSGWMJJ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;prop-2-enoic acid Chemical group OC(=O)C=C.CC(=C)C(O)=O MUZDXNQOSGWMJJ-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229920000249 biocompatible polymer Polymers 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
Classifications
-
- 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
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B17/00—Surgical instruments, devices or methods
- A61B17/00491—Surgical glue applicators
-
- 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
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B17/00—Surgical instruments, devices or methods
- A61B17/00491—Surgical glue applicators
- A61B2017/005—Surgical glue applicators hardenable using external energy source, e.g. laser, ultrasound
Landscapes
- Health & Medical Sciences (AREA)
- Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Medical Informatics (AREA)
- Molecular Biology (AREA)
- Materials For Medical Uses (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1554583A FR3036288B1 (fr) | 2015-05-21 | 2015-05-21 | Colles chirurgicales |
| FR1554583 | 2015-05-21 | ||
| PCT/FR2016/051211 WO2016185153A1 (fr) | 2015-05-21 | 2016-05-20 | Colles chirurgicales |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018517477A JP2018517477A (ja) | 2018-07-05 |
| JP2018517477A5 JP2018517477A5 (enExample) | 2021-10-07 |
| JP7019884B2 true JP7019884B2 (ja) | 2022-02-16 |
Family
ID=54140580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017560619A Active JP7019884B2 (ja) | 2015-05-21 | 2016-05-20 | 外科用接着剤 |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US11207443B2 (enExample) |
| EP (1) | EP3297692B1 (enExample) |
| JP (1) | JP7019884B2 (enExample) |
| CN (1) | CN107771086B (enExample) |
| AU (1) | AU2016263552A1 (enExample) |
| CA (1) | CA2986308A1 (enExample) |
| ES (1) | ES2908874T3 (enExample) |
| FR (1) | FR3036288B1 (enExample) |
| WO (1) | WO2016185153A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108815560B (zh) * | 2018-06-21 | 2021-03-12 | 广州迈普再生医学科技股份有限公司 | 多孔组织封堵材料及其制备方法和封堵制品 |
| CN111150878B (zh) * | 2018-11-07 | 2022-03-15 | 财团法人工业技术研究院 | 生物可分解的封合胶及其用途 |
| FR3093000B1 (fr) * | 2019-02-21 | 2022-08-26 | Bertrand Perrin | colles chirurgicales à base de monomères comprenant une fonction phosphate |
| FR3113464B1 (fr) * | 2020-08-20 | 2023-07-14 | Cohesives | Colles chirurgicales |
| CN113350564B (zh) * | 2021-05-20 | 2023-03-10 | 诺一迈尔(苏州)生命科技有限公司 | 生物可降解组织粘合贴片及其制备方法 |
| EP4479101A1 (fr) | 2022-02-18 | 2024-12-25 | Cohesives | Composition photopolymerisable pour adhesif pour tissus biologiques |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009247437A (ja) | 2008-04-02 | 2009-10-29 | Nitto Denko Corp | 生体接着剤組成物及びその使用方法 |
| US20140194887A1 (en) | 2011-08-15 | 2014-07-10 | Vivek Shenoy | Device, Composition and Method for Prevention of Bone Fracture and Pain |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4181752A (en) * | 1974-09-03 | 1980-01-01 | Minnesota Mining And Manufacturing Company | Acrylic-type pressure sensitive adhesives by means of ultraviolet radiation curing |
| EP1375617A1 (en) * | 2002-06-19 | 2004-01-02 | 3M Innovative Properties Company | Radiation-curable, solvent-free and printable precursor of a pressure-sensitive adhesive |
| EP1389633A1 (en) * | 2002-08-14 | 2004-02-18 | The Procter & Gamble Company | Improved thermoplastic hydrophilic adhesive compositions for dry and wet surfaces the compositions having an increased water adhesion stability |
| US7045559B2 (en) * | 2003-12-18 | 2006-05-16 | Kimberly-Clark Worldwide, Inc. | Electrically conductive adhesive hydrogels with solubilizer |
| US20060035997A1 (en) * | 2004-08-10 | 2006-02-16 | Orlowski Jan A | Curable acrylate polymer compositions featuring improved flexural characteristics |
| US20060173124A1 (en) * | 2005-02-01 | 2006-08-03 | National Starch And Chemical Investment Holding Corporation | Solution pressure sensitive adhesives based on acrylic block copolymers |
| JP2009518135A (ja) * | 2005-12-07 | 2009-05-07 | ズィマー・インコーポレーテッド | 照射を使用してハイドロゲルを結合させるまたは改質する方法 |
| WO2008075806A1 (en) * | 2006-12-19 | 2008-06-26 | Hak Soo Han | Photo-curable coating composition comprising hyperbranched structure prepolymer, method for preparing the same and product prepared by the same |
| PT1994886E (pt) * | 2007-05-24 | 2013-10-09 | Henkel Ag & Co Kgaa | Ponta de aplicador para aplicação de cola cirúrgica |
| US8256233B2 (en) * | 2008-10-31 | 2012-09-04 | The Invention Science Fund I, Llc | Systems, devices, and methods for making or administering frozen particles |
| JP2010157706A (ja) * | 2008-12-03 | 2010-07-15 | Fujifilm Corp | 光インプリント用硬化性組成物およびそれを用いた硬化物の製造方法 |
| US9314546B2 (en) * | 2009-11-20 | 2016-04-19 | Mitsui Chemicals, Inc. | Adhesive composition for soft tissues, adhesive composition for wound dressing or wound dressing composition |
| DE102010013799A1 (de) * | 2010-04-03 | 2011-10-06 | Lohmann Gmbh & Co Kg | Acrylathaftklebstoff für Anwendungen auf der Haut |
| CN101870650A (zh) * | 2010-07-16 | 2010-10-27 | 北京化工大学常州先进材料研究院 | 一种可光聚合的粘合剂单体的制备与应用 |
| US8871512B2 (en) * | 2010-10-27 | 2014-10-28 | Empire Technology Development Llc | Biocompatible polymerizable acrylate products and methods |
| US20130266664A1 (en) * | 2010-12-20 | 2013-10-10 | Virginia Commonwealth University | Facile method for crosslinking and incorporating bioactive molecules into electrospun fiber scaffolds |
| JP6387499B2 (ja) * | 2012-11-21 | 2018-09-12 | アルケア株式会社 | 皮膚用粘着剤組成物、皮膚用粘着剤及び皮膚用粘着シート |
| CN104623725B (zh) * | 2014-12-31 | 2017-01-18 | 深圳清华大学研究院 | 生物粘合剂及其制备方法 |
-
2015
- 2015-05-21 FR FR1554583A patent/FR3036288B1/fr active Active
-
2016
- 2016-05-20 US US15/575,678 patent/US11207443B2/en active Active
- 2016-05-20 WO PCT/FR2016/051211 patent/WO2016185153A1/fr not_active Ceased
- 2016-05-20 CN CN201680029436.0A patent/CN107771086B/zh active Active
- 2016-05-20 AU AU2016263552A patent/AU2016263552A1/en not_active Abandoned
- 2016-05-20 ES ES16732691T patent/ES2908874T3/es active Active
- 2016-05-20 CA CA2986308A patent/CA2986308A1/fr active Pending
- 2016-05-20 JP JP2017560619A patent/JP7019884B2/ja active Active
- 2016-05-20 EP EP16732691.7A patent/EP3297692B1/fr active Active
-
2021
- 2021-12-27 US US17/562,381 patent/US12239759B2/en active Active
-
2025
- 2025-01-27 US US19/037,365 patent/US20250170299A1/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009247437A (ja) | 2008-04-02 | 2009-10-29 | Nitto Denko Corp | 生体接着剤組成物及びその使用方法 |
| US20140194887A1 (en) | 2011-08-15 | 2014-07-10 | Vivek Shenoy | Device, Composition and Method for Prevention of Bone Fracture and Pain |
Non-Patent Citations (1)
| Title |
|---|
| Journal of Applied Polymer Science，2013年，Vol.127，No.6，p.5051-5058 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107771086B (zh) | 2021-11-05 |
| CA2986308A1 (fr) | 2016-11-24 |
| ES2908874T3 (es) | 2022-05-04 |
| US12239759B2 (en) | 2025-03-04 |
| FR3036288B1 (fr) | 2018-10-26 |
| FR3036288A1 (fr) | 2016-11-25 |
| US20250170299A1 (en) | 2025-05-29 |
| US20180280564A1 (en) | 2018-10-04 |
| EP3297692B1 (fr) | 2022-01-05 |
| WO2016185153A1 (fr) | 2016-11-24 |
| JP2018517477A (ja) | 2018-07-05 |
| AU2016263552A1 (en) | 2018-01-04 |
| EP3297692A1 (fr) | 2018-03-28 |
| US11207443B2 (en) | 2021-12-28 |
| CN107771086A (zh) | 2018-03-06 |
| US20220143264A1 (en) | 2022-05-12 |
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