AU2001294727A1 - In-situ bonds - Google Patents
In-situ bondsInfo
- Publication number
- AU2001294727A1 AU2001294727A1 AU2001294727A AU9472701A AU2001294727A1 AU 2001294727 A1 AU2001294727 A1 AU 2001294727A1 AU 2001294727 A AU2001294727 A AU 2001294727A AU 9472701 A AU9472701 A AU 9472701A AU 2001294727 A1 AU2001294727 A1 AU 2001294727A1
- Authority
- AU
- Australia
- Prior art keywords
- bond
- adhesive
- tissue
- polyisocyanate
- polyols
- 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
- 238000011065 in-situ storage Methods 0.000 title description 3
- 239000000853 adhesive Substances 0.000 claims description 78
- 230000001070 adhesive effect Effects 0.000 claims description 78
- 239000005056 polyisocyanate Substances 0.000 claims description 54
- 229920001228 polyisocyanate Polymers 0.000 claims description 54
- 229920005862 polyol Polymers 0.000 claims description 41
- 150000003077 polyols Chemical class 0.000 claims description 40
- 150000002009 diols Chemical class 0.000 claims description 37
- 150000004072 triols Chemical class 0.000 claims description 36
- 239000012948 isocyanate Substances 0.000 claims description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- 150000002513 isocyanates Chemical class 0.000 claims description 30
- 239000000017 hydrogel Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 16
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical group CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 12
- 125000006353 oxyethylene group Chemical group 0.000 claims description 12
- 239000003106 tissue adhesive Substances 0.000 claims description 12
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 230000009257 reactivity Effects 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000008096 xylene Substances 0.000 claims description 7
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 6
- 239000012530 fluid Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 5
- 239000004472 Lysine Substances 0.000 claims description 5
- XLYZHIKLGNTFFX-UHFFFAOYSA-N 1,2,3,5-tetrafluoro-4,6-diisocyanatobenzene Chemical compound FC1=C(F)C(N=C=O)=C(F)C(N=C=O)=C1F XLYZHIKLGNTFFX-UHFFFAOYSA-N 0.000 claims description 4
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical group O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- 230000002439 hemostatic effect Effects 0.000 claims description 2
- 230000000149 penetrating effect Effects 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229920001223 polyethylene glycol Polymers 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 10
- 239000002202 Polyethylene glycol Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- -1 ethylene oxide diols Chemical class 0.000 description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000012662 bulk polymerization Methods 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229920002176 Pluracol® Polymers 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004925 denaturation Methods 0.000 description 2
- 230000036425 denaturation Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000011874 heated mixture Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003894 surgical glue Substances 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- WOGVOIWHWZWYOZ-UHFFFAOYSA-N 1,1-diisocyanatoethane Chemical compound O=C=NC(C)N=C=O WOGVOIWHWZWYOZ-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- JFRQLKNEDLLXOQ-UHFFFAOYSA-N 1,3-diisocyanato-2,4-dimethylbenzene Chemical compound CC1=CC=C(N=C=O)C(C)=C1N=C=O JFRQLKNEDLLXOQ-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- KIAZLPPFFCCZJS-UHFFFAOYSA-N 1,5-diisocyanato-2,3-dimethylbenzene Chemical compound CC1=CC(N=C=O)=CC(N=C=O)=C1C KIAZLPPFFCCZJS-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- SZBXTBGNJLZMHB-UHFFFAOYSA-N 1-chloro-2,4-diisocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1N=C=O SZBXTBGNJLZMHB-UHFFFAOYSA-N 0.000 description 1
- SIYBFAKKDKDECW-UHFFFAOYSA-N 1-ethoxy-2,4-diisocyanatobenzene Chemical compound CCOC1=CC=C(N=C=O)C=C1N=C=O SIYBFAKKDKDECW-UHFFFAOYSA-N 0.000 description 1
- PAUHLEIGHAUFAK-UHFFFAOYSA-N 1-isocyanato-1-[(1-isocyanatocyclohexyl)methyl]cyclohexane Chemical compound C1CCCCC1(N=C=O)CC1(N=C=O)CCCCC1 PAUHLEIGHAUFAK-UHFFFAOYSA-N 0.000 description 1
- QILYSOTYPKBIDW-UHFFFAOYSA-N 2,4-diisocyanato-1-(2-phenylethenyl)benzene Chemical compound O=C=NC1=CC(N=C=O)=CC=C1C=CC1=CC=CC=C1 QILYSOTYPKBIDW-UHFFFAOYSA-N 0.000 description 1
- DZDVHNPXFWWDRM-UHFFFAOYSA-N 2,4-diisocyanato-1-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1N=C=O DZDVHNPXFWWDRM-UHFFFAOYSA-N 0.000 description 1
- GBPMCEJJWVOYOG-UHFFFAOYSA-N 2,6-diisocyanato-1-benzofuran Chemical compound C1=C(N=C=O)C=C2OC(N=C=O)=CC2=C1 GBPMCEJJWVOYOG-UHFFFAOYSA-N 0.000 description 1
- YTZRFUSYPGFDNC-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methyloxirane;oxirane Chemical compound C1CO1.CC1CO1.CCC(CO)(CO)CO YTZRFUSYPGFDNC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- 229920001651 Cyanoacrylate Polymers 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 102000009123 Fibrin Human genes 0.000 description 1
- 108010073385 Fibrin Proteins 0.000 description 1
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 1
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- VWYHWAHYVKZKHI-UHFFFAOYSA-N N=C=O.N=C=O.C1=CC(N)=CC=C1C1=CC=C(N)C=C1 Chemical compound N=C=O.N=C=O.C1=CC(N)=CC=C1C1=CC=C(N)C=C1 VWYHWAHYVKZKHI-UHFFFAOYSA-N 0.000 description 1
- 229920002166 Pluracol® V 10 Polymers 0.000 description 1
- 241001415846 Procellariidae Species 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 208000031737 Tissue Adhesions Diseases 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000012085 chronic inflammatory response Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229950003499 fibrin Drugs 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 229940071676 hydroxypropylcellulose Drugs 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4808—Mixtures of two or more polyetherdiols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
- C08G18/7642—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2210/00—Compositions for preparing hydrogels
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials For Medical Uses (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/676,851 | 2000-09-29 | ||
| US09/676,851 US6524327B1 (en) | 2000-09-29 | 2000-09-29 | In-situ bonds |
| PCT/US2001/030055 WO2002026848A2 (fr) | 2000-09-29 | 2001-09-26 | Liaisons in-situ |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2001294727A1 true AU2001294727A1 (en) | 2002-04-08 |
Family
ID=24716277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001294727A Abandoned AU2001294727A1 (en) | 2000-09-29 | 2001-09-26 | In-situ bonds |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6524327B1 (fr) |
| EP (1) | EP1335690A4 (fr) |
| JP (1) | JP2004525660A (fr) |
| AU (1) | AU2001294727A1 (fr) |
| CA (1) | CA2423952A1 (fr) |
| WO (1) | WO2002026848A2 (fr) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6296607B1 (en) * | 2000-10-20 | 2001-10-02 | Praxis, Llc. | In situ bulking device |
| US8501165B2 (en) * | 2001-12-12 | 2013-08-06 | Promethean Surgical Devices Llc | In situ bonds |
| US20040068078A1 (en) * | 2001-12-12 | 2004-04-08 | Milbocker Michael T. | In situ polymerizing medical compositions |
| DE10304153A1 (de) * | 2002-02-08 | 2003-11-13 | Henkel Kgaa | Farbneutraler 1K Polyurethan-Klebstoff |
| US7309310B2 (en) * | 2002-04-09 | 2007-12-18 | Promethean Surgical Devices | Treatment for gastroesophageal disease |
| US7047980B2 (en) * | 2002-04-09 | 2006-05-23 | Promethean Surgical Devices Llc | Treatment for Gastroesophageal disease |
| JP4916113B2 (ja) * | 2002-11-25 | 2012-04-11 | ボストン サイエンティフィック リミテッド | 注入装置 |
| US7632294B2 (en) * | 2003-09-29 | 2009-12-15 | Promethean Surgical Devices, Llc | Devices and methods for spine repair |
| US7955788B2 (en) * | 2003-10-30 | 2011-06-07 | Medtronic, Inc. | Bioprosthetic tissue preparation with synthetic hydrogels |
| US20050125033A1 (en) * | 2003-12-04 | 2005-06-09 | Mcnally-Heintzelman Karen M. | Wound closure apparatus |
| US20050125015A1 (en) * | 2003-12-04 | 2005-06-09 | Mcnally-Heintzelman Karen M. | Tissue-handling apparatus, system and method |
| WO2005055958A2 (fr) * | 2003-12-09 | 2005-06-23 | Promethean Surgical Devices Llc | Adhesif chirurgical ameliore et applications de celui-ci |
| US20050228433A1 (en) * | 2004-03-16 | 2005-10-13 | Weenna Bucay-Couto | In situ implant and method of forming same |
| WO2005094724A1 (fr) * | 2004-03-29 | 2005-10-13 | Promethean Surgical Devices Llc | Formulations d'adhesifs chirurgicaux et procedes de preparation |
| US20050288566A1 (en) * | 2004-04-30 | 2005-12-29 | Levendusky Joseph A | Apparatus with partially insulated needle for measuring tissue impedance |
| US20090088846A1 (en) | 2007-04-17 | 2009-04-02 | David Myung | Hydrogel arthroplasty device |
| US8262693B2 (en) * | 2004-11-05 | 2012-09-11 | Accessclosure, Inc. | Apparatus and methods for sealing a vascular puncture |
| US8470954B2 (en) | 2005-01-10 | 2013-06-25 | Ethicon, Inc. | Diisocyanate terminated macromer and formulation thereof for use as an internal adhesive or sealant |
| US20070167617A1 (en) * | 2006-01-17 | 2007-07-19 | Fitz Benjamin D | Method of making a diisocyanate terminated macromer |
| US7968668B2 (en) | 2005-01-10 | 2011-06-28 | Ethicon Inc. | Diisocyanate terminated macromer and formulation thereof for use as an internal adhesive or sealant |
| US20060153796A1 (en) * | 2005-01-10 | 2006-07-13 | Fitz Benjamin D | Diisocyanate terminated macromer and formulation thereof for use as an internal adhesive or sealant |
| US7728097B2 (en) * | 2005-01-10 | 2010-06-01 | Ethicon, Inc. | Method of making a diisocyanate terminated macromer |
| US20060233852A1 (en) * | 2005-04-19 | 2006-10-19 | Promethean Surgical Devices | Prosthetic for tissue reinforcement |
| JP5088894B2 (ja) * | 2005-12-06 | 2012-12-05 | タイコ ヘルスケア グループ リミテッド パートナーシップ | 生体適合性組織封止剤および接着剤 |
| EP1966311A4 (fr) * | 2005-12-08 | 2012-08-15 | Tyco Healthcare | Compositions pulverisables a viscosite reduite |
| NZ570477A (en) * | 2006-01-27 | 2011-07-29 | Univ Pittsburgh | Medical adhesive and methods of tissue adhesion |
| EP1815875B1 (fr) * | 2006-02-06 | 2015-08-12 | nolax AG | Pansement avec un adhesif de pression a base de polyurethane et son procédé de revêtement d'extrusion |
| DE102006016636A1 (de) * | 2006-04-08 | 2007-10-18 | Bayer Materialscience Ag | Polyurethan-Schäume für die Wundbehandlung |
| US8629195B2 (en) | 2006-04-08 | 2014-01-14 | Bayer Materialscience Ag | Production of polyurethane foams |
| US9289279B2 (en) * | 2006-10-06 | 2016-03-22 | Promethean Surgical Devices, Llc | Apparatus and method for limiting surgical adhesions |
| US20080110961A1 (en) * | 2006-11-10 | 2008-05-15 | Ethicon Endo-Surgery, Inc. | Initiator Coating of Staples |
| US20090177192A1 (en) * | 2007-07-13 | 2009-07-09 | Scimed Life Systems, Inc. | Method for ablating tissue to facilitate implantation and apparatus and kit for use therewith |
| US8182647B2 (en) | 2007-07-23 | 2012-05-22 | Cohera Medical, Inc. | Hydrophilic biodegradable adhesives |
| EP2045279A1 (fr) * | 2007-10-05 | 2009-04-08 | Bayer MaterialScience AG | Mousses de polyuréthane pour le traitement de plaies |
| DE102007048078A1 (de) | 2007-10-05 | 2009-04-09 | Bayer Materialscience Ag | Polyurethan-Schäume für die Wundbehandlung |
| US8262626B2 (en) * | 2007-10-23 | 2012-09-11 | Boston Scientific Scimed, Inc. | Apparatus and method for treating tissue |
| US8287566B2 (en) | 2007-10-26 | 2012-10-16 | Cohera Medical, Inc. | Spray devices and methods |
| US8071663B2 (en) * | 2008-02-29 | 2011-12-06 | Ethicon, Inc. | Medically acceptable formulation of a diisocyanate terminated macromer for use as an internal adhesive or sealant |
| US8324292B2 (en) * | 2008-02-29 | 2012-12-04 | Ethicon, Inc. | Medically acceptable formulation of a diisocyanate terminated macromer for use as an internal adhesive or sealant |
| WO2009117737A2 (fr) * | 2008-03-21 | 2009-09-24 | Biomimedica, Inc | Procédés, dispositifs et compositions permettant de faire adhérer des implants polymères hydratés sur un os |
| DE102008023798A1 (de) | 2008-05-15 | 2009-11-19 | Hans Hermann Schulz | Hydrogel |
| US20120209396A1 (en) | 2008-07-07 | 2012-08-16 | David Myung | Orthopedic implants having gradient polymer alloys |
| JP5722773B2 (ja) | 2008-08-05 | 2015-05-27 | バイオミメディカ インコーポレイテッド | ポリウレタングラフト化ヒドロゲル |
| AR074999A1 (es) | 2009-01-24 | 2011-03-02 | Bayer Materialscience Ag | Espumas de dispersion de poliuretano de dos componentes |
| US20110202016A1 (en) * | 2009-08-24 | 2011-08-18 | Arsenal Medical, Inc. | Systems and methods relating to polymer foams |
| CN106913902A (zh) | 2009-11-09 | 2017-07-04 | 聚光灯技术合伙有限责任公司 | 多糖基水凝胶 |
| EP2498764B1 (fr) | 2009-11-09 | 2017-09-06 | Spotlight Technology Partners LLC | Hydrogels fragmentés |
| WO2012027678A1 (fr) | 2010-08-27 | 2012-03-01 | Biomimedica, Inc. | Réseaux de polymère hydrophobe et hydrophile interpénétrant dérivés de polymères hydrophobes et procédés de préparation de ceux-ci |
| US11484627B2 (en) | 2010-10-20 | 2022-11-01 | 206 Ortho, Inc. | Method and apparatus for treating bone fractures, and/or for fortifying and/or augmenting bone, including the provision and use of composite implants, and novel composite structures which may be used for medical and non-medical applications |
| WO2014190289A2 (fr) | 2013-05-23 | 2014-11-27 | 206 Ortho, Inc. | Procédé et appareil permettant de traiter les fractures osseuses, et/ou de fortifier et/ou d'augmenter la masse osseuse, comprenant la fourniture et l'utilisation d'implants composites |
| US10525169B2 (en) | 2010-10-20 | 2020-01-07 | 206 Ortho, Inc. | Method and apparatus for treating bone fractures, and/or for fortifying and/or augmenting bone, including the provision and use of composite implants, and novel composite structures which may be used for medical and non-medical applications |
| WO2015095745A1 (fr) | 2010-10-20 | 2015-06-25 | 206 Ortho, Inc. | Méthode et appareil pour le traitement de fractures osseuses, et/ou pour la fortification et/ou l'augmentation de la masse osseuse, notamment l'apport et l'utilisation d'implants composites, et nouvelles structures composites pouvant être utilisées pour des applications médicales et non médicales |
| US11207109B2 (en) | 2010-10-20 | 2021-12-28 | 206 Ortho, Inc. | Method and apparatus for treating bone fractures, and/or for fortifying and/or augmenting bone, including the provision and use of composite implants, and novel composite structures which may be used for medical and non-medical applications |
| WO2012054742A2 (fr) * | 2010-10-20 | 2012-04-26 | BIOS2 Medical, Inc. | Polymère implantable pour lésions osseuses et vasculaires |
| US11058796B2 (en) | 2010-10-20 | 2021-07-13 | 206 Ortho, Inc. | Method and apparatus for treating bone fractures, and/or for fortifying and/or augmenting bone, including the provision and use of composite implants, and novel composite structures which may be used for medical and non-medical applications |
| US11291483B2 (en) | 2010-10-20 | 2022-04-05 | 206 Ortho, Inc. | Method and apparatus for treating bone fractures, and/or for fortifying and/or augmenting bone, including the provision and use of composite implants |
| KR20140115294A (ko) | 2011-10-03 | 2014-09-30 | 바이오미메디카, 인코포레이티드 | 순응성 재료들을 또 다른 표면으로 앵커링하기 위한 중합체성 접착제 |
| EP3335673B1 (fr) | 2011-11-21 | 2025-07-30 | Hyalex Orthopaedics, Inc. | Systèmes d'ancrage d'implants orthopédiques aux os |
| EP2819620A4 (fr) | 2012-02-29 | 2015-11-04 | 206 Ortho Inc | Procédé et appareil destinés à traiter des fractures osseuses, comprenant l'utilisation d'implants composites |
| US10968310B1 (en) | 2015-04-28 | 2021-04-06 | Adhesive R&D, Inc. | Polymerizable materials, anaerobically curable compositions, and related methods and products |
| US11077228B2 (en) | 2015-08-10 | 2021-08-03 | Hyalex Orthopaedics, Inc. | Interpenetrating polymer networks |
| US10869950B2 (en) | 2018-07-17 | 2020-12-22 | Hyalex Orthopaedics, Inc. | Ionic polymer compositions |
| US11801143B2 (en) | 2021-07-01 | 2023-10-31 | Hyalex Orthopaedics, Inc. | Multi-layered biomimetic osteochondral implants and methods of using thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4057535A (en) * | 1976-04-14 | 1977-11-08 | Tatyana Esperovna Lipatova | Adhesive for gluing together soft body tissues |
| US4740534A (en) * | 1985-08-30 | 1988-04-26 | Sanyo Chemical Industries, Ltd. | Surgical adhesive |
| US4743632A (en) * | 1987-02-25 | 1988-05-10 | Pfizer Hospital Products Group, Inc. | Polyetherurethane urea polymers as space filling tissue adhesives |
| IL94910A (en) * | 1990-06-29 | 1994-04-12 | Technion Research Dev Foundati | Biomedical adhesive compositions |
| JPH04150866A (ja) * | 1990-10-15 | 1992-05-25 | Nisshinbo Ind Inc | 外科用接着剤 |
| JP2928892B2 (ja) * | 1990-11-27 | 1999-08-03 | 三洋化成工業株式会社 | 外科用接着剤 |
| US5785642A (en) * | 1996-10-18 | 1998-07-28 | Micro Therapeutics, Inc. | Methods for treating urinary incontinence in mammals |
| CA2358565A1 (fr) * | 1999-01-22 | 2000-07-27 | Peter S. Dardi | Adhesifs medicaux |
| US6296607B1 (en) * | 2000-10-20 | 2001-10-02 | Praxis, Llc. | In situ bulking device |
-
2000
- 2000-09-29 US US09/676,851 patent/US6524327B1/en not_active Expired - Fee Related
-
2001
- 2001-09-26 EP EP01975394A patent/EP1335690A4/fr not_active Withdrawn
- 2001-09-26 JP JP2002531228A patent/JP2004525660A/ja active Pending
- 2001-09-26 CA CA002423952A patent/CA2423952A1/fr not_active Abandoned
- 2001-09-26 WO PCT/US2001/030055 patent/WO2002026848A2/fr not_active Ceased
- 2001-09-26 AU AU2001294727A patent/AU2001294727A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002026848A2 (fr) | 2002-04-04 |
| WO2002026848A3 (fr) | 2003-06-12 |
| EP1335690A4 (fr) | 2004-03-31 |
| EP1335690A2 (fr) | 2003-08-20 |
| US6524327B1 (en) | 2003-02-25 |
| JP2004525660A (ja) | 2004-08-26 |
| CA2423952A1 (fr) | 2002-04-04 |
| WO2002026848B1 (fr) | 2003-10-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |