JP2018517477A5 - - Google Patents
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- Publication number
- JP2018517477A5 JP2018517477A5 JP2017560619A JP2017560619A JP2018517477A5 JP 2018517477 A5 JP2018517477 A5 JP 2018517477A5 JP 2017560619 A JP2017560619 A JP 2017560619A JP 2017560619 A JP2017560619 A JP 2017560619A JP 2018517477 A5 JP2018517477 A5 JP 2018517477A5
- Authority
- JP
- Japan
- Prior art keywords
- composition according
- methacrylate
- composition
- acrylic acid
- acrylate
- 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.)
- Granted
Links
- 239000000178 monomer Substances 0.000 claims description 14
- -1 carbamate ester Chemical class 0.000 claims description 13
- 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 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 32
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 4
- 239000003431 cross linking reagent Substances 0.000 claims 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 3
- 239000003999 initiator Substances 0.000 claims 3
- 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 2
- 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 2
- 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 2
- 229930185605 Bisphenol Natural products 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 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 2
- 125000004386 diacrylate group Chemical group 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 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
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-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
- 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 1
- AOUSBQVEVZBMNI-UHFFFAOYSA-N 2-bromoethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCBr AOUSBQVEVZBMNI-UHFFFAOYSA-N 0.000 claims 1
- FEUFEGJTJIHPOF-UHFFFAOYSA-N 2-butyl acrylic acid Chemical group CCCCC(=C)C(O)=O FEUFEGJTJIHPOF-UHFFFAOYSA-N 0.000 claims 1
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 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 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 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 1
- 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 1
- 239000000853 adhesive Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims 1
- JNNKWUPPLJTSSJ-UHFFFAOYSA-N chloromethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCl JNNKWUPPLJTSSJ-UHFFFAOYSA-N 0.000 claims 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 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 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical group OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims 1
- 230000003100 immobilizing effect Effects 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 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 1
- 238000000034 method Methods 0.000 claims 1
- 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 1
- 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 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 230000003014 reinforcing effect Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
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 true JP2018517477A5 (https=) | 2021-10-07 |
| JP7019884B2 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 (8)
| Country | Link |
|---|---|
| US (3) | US11207443B2 (https=) |
| EP (1) | EP3297692B1 (https=) |
| JP (1) | JP7019884B2 (https=) |
| CN (1) | CN107771086B (https=) |
| AU (1) | AU2016263552A1 (https=) |
| ES (1) | ES2908874T3 (https=) |
| FR (1) | FR3036288B1 (https=) |
| WO (1) | WO2016185153A1 (https=) |
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 |
| EP4479101B1 (fr) | 2022-02-18 | 2026-03-04 | Cohesives | Composition photopolymerisable pour adhesif pour tissus biologiques |
Family Cites Families (20)
| 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 |
| 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 |
| US8485861B2 (en) * | 2008-10-31 | 2013-07-16 | 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 |
| KR101606967B1 (ko) * | 2009-11-20 | 2016-03-28 | 미쓰이 가가쿠 가부시키가이샤 | 연조직용 접착제 조성물, 창상 피복용 접착제 조성물 또는 창상 피복제 조성물 |
| 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 |
| WO2012057748A1 (en) * | 2010-10-27 | 2012-05-03 | Empire Technology Development Llc | Biocompatible polymerizable acrylate products and methods |
| WO2012088059A2 (en) * | 2010-12-20 | 2012-06-28 | Virginia Commonwealth University | A facile method for crosslinking and incorporating bioactive molecules into electrospun fiber scaffolds |
| WO2013025504A1 (en) * | 2011-08-15 | 2013-02-21 | Vivek Shenoy | Device, composition and method for prevention of bone fracture and pain |
| EP2924092A4 (en) * | 2012-11-21 | 2016-10-12 | Alcare Co Ltd | HAFFET COMPOSITION, HAIR SKIN AND HAIR SKIN |
| 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 WO PCT/FR2016/051211 patent/WO2016185153A1/fr not_active Ceased
- 2016-05-20 ES ES16732691T patent/ES2908874T3/es active Active
- 2016-05-20 US US15/575,678 patent/US11207443B2/en active Active
- 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 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
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