IL94910A - Biomedical adhesive compositions - Google Patents

Biomedical adhesive compositions

Info

Publication number: IL94910A
Authority: IL; Israel
Prior art keywords: elastomeric; adhesive composition; composition according; biomedical adhesive; polyisocyanate
Prior art date: 1990-06-29

Application number

IL9491090A

Other languages

English (en)

Other versions

IL94910A0 (en

Inventor

Katz Dov

Brandeis Esther

Klein Joachim

Original Assignee

Technion Research Dev Foundati

Gbf

Priority date (The priority date 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 date listed.)

1990-06-29

Filing date

1990-06-29

Publication date

1994-04-12

1990-06-29 Application filed by Technion Research Dev Foundati, Gbf filed Critical Technion Research Dev Foundati

1990-06-29 Priority to IL9491090A priority Critical patent/IL94910A/en

1991-04-15 Publication of IL94910A0 publication Critical patent/IL94910A0/xx

1991-06-27 Priority to US07/722,088 priority patent/US5266608A/en

1991-06-28 Priority to DE69114931T priority patent/DE69114931T2/de

1991-06-28 Priority to EP91401786A priority patent/EP0466552B1/de

1991-06-28 Priority to JP3158611A priority patent/JPH05111530A/ja

1991-06-28 Priority to CA002045964A priority patent/CA2045964C/en

1994-04-12 Publication of IL94910A publication Critical patent/IL94910A/en

Links

230000001070 adhesive effect Effects 0.000 title claims description 70
239000000853 adhesive Substances 0.000 title claims description 68
239000000203 mixture Substances 0.000 title claims description 67
239000005056 polyisocyanate Substances 0.000 claims description 18
229920001228 polyisocyanate Polymers 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 14
229920005862 polyol Polymers 0.000 claims description 13
150000003077 polyols Chemical class 0.000 claims description 13
239000003153 chemical reaction reagent Substances 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
159000000007 calcium salts Chemical class 0.000 claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
-1 poly-alkylene ether Chemical compound 0.000 claims description 6
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
239000011575 calcium Substances 0.000 claims description 5
229910052791 calcium Inorganic materials 0.000 claims description 5
239000011574 phosphorus Substances 0.000 claims description 5
229910052698 phosphorus Inorganic materials 0.000 claims description 5
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000000945 filler Substances 0.000 claims description 4
150000002334 glycols Chemical class 0.000 claims description 4
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
239000000843 powder Substances 0.000 claims description 4
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 3
GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 claims description 3
VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 claims description 3
ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 3
239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
229910052588 hydroxylapatite Inorganic materials 0.000 claims description 3
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 3
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 3
229920001281 polyalkylene Polymers 0.000 claims description 3
229920000728 polyester Polymers 0.000 claims description 3
238000009736 wetting Methods 0.000 claims description 3
XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 claims description 2
239000004925 Acrylic resin Substances 0.000 claims description 2
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 claims description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
239000001506 calcium phosphate Substances 0.000 claims description 2
239000006229 carbon black Substances 0.000 claims description 2
239000000919 ceramic Substances 0.000 claims description 2
229910044991 metal oxide Inorganic materials 0.000 claims description 2
150000004706 metal oxides Chemical class 0.000 claims description 2
239000000113 methacrylic resin Substances 0.000 claims description 2
239000004014 plasticizer Substances 0.000 claims description 2
229940035044 sorbitan monolaurate Drugs 0.000 claims description 2
239000001587 sorbitan monostearate Substances 0.000 claims description 2
235000011076 sorbitan monostearate Nutrition 0.000 claims description 2
229940035048 sorbitan monostearate Drugs 0.000 claims description 2
239000003381 stabilizer Substances 0.000 claims description 2
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 2
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 2
229940078499 tricalcium phosphate Drugs 0.000 claims description 2
229910000391 tricalcium phosphate Inorganic materials 0.000 claims description 2
235000019731 tricalcium phosphate Nutrition 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims 3
150000002513 isocyanates Chemical class 0.000 claims 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
125000005628 tolylene group Chemical group 0.000 claims 2
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 claims 1
102000004190 Enzymes Human genes 0.000 claims 1
108090000790 Enzymes Proteins 0.000 claims 1
239000005057 Hexamethylene diisocyanate Substances 0.000 claims 1
229920001219 Polysorbate 40 Polymers 0.000 claims 1
125000002723 alicyclic group Chemical group 0.000 claims 1
125000001931 aliphatic group Chemical group 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
239000001593 sorbitan monooleate Substances 0.000 claims 1
235000011069 sorbitan monooleate Nutrition 0.000 claims 1
229940035049 sorbitan monooleate Drugs 0.000 claims 1
210000000988 bone and bone Anatomy 0.000 description 28
210000001519 tissue Anatomy 0.000 description 22
238000002474 experimental method Methods 0.000 description 12
208000010392 Bone Fractures Diseases 0.000 description 8
230000035876 healing Effects 0.000 description 8
238000007654 immersion Methods 0.000 description 8
239000003054 catalyst Substances 0.000 description 7
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 7
239000002953 phosphate buffered saline Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
238000004026 adhesive bonding Methods 0.000 description 6
239000000470 constituent Substances 0.000 description 6
239000011521 glass Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
206010017076 Fracture Diseases 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
238000000034 method Methods 0.000 description 5
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 5
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 5
229920001213 Polysorbate 20 Polymers 0.000 description 4
239000012634 fragment Substances 0.000 description 4
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
229920000053 polysorbate 80 Polymers 0.000 description 4
239000000126 substance Substances 0.000 description 4
210000002303 tibia Anatomy 0.000 description 4
238000001727 in vivo Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
230000008569 process Effects 0.000 description 3
238000001356 surgical procedure Methods 0.000 description 3
HXYDAOXNYINGCS-UHFFFAOYSA-J 2-ethylhexanoate;tin(4+) Chemical compound [Sn+4].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O HXYDAOXNYINGCS-UHFFFAOYSA-J 0.000 description 2
229920001651 Cyanoacrylate Polymers 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
230000004888 barrier function Effects 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000007853 buffer solution Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000007857 degradation product Substances 0.000 description 2
239000003292 glue Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
230000003993 interaction Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000004632 polycaprolactone Substances 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229920000136 polysorbate Polymers 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
230000008439 repair process Effects 0.000 description 2
238000011160 research Methods 0.000 description 2
238000012552 review Methods 0.000 description 2
210000003491 skin Anatomy 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
210000004872 soft tissue Anatomy 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
238000012360 testing method Methods 0.000 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 description 2
CPKVUHPKYQGHMW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;molecular iodine Chemical compound II.C=CN1CCCC1=O CPKVUHPKYQGHMW-UHFFFAOYSA-N 0.000 description 1
ODWNBAWYDSWOAF-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yloxybenzene Chemical compound CC(C)(C)CC(C)(C)OC1=CC=CC=C1 ODWNBAWYDSWOAF-UHFFFAOYSA-N 0.000 description 1
AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
ULUYRVWYCIOFRV-UHFFFAOYSA-K 2-ethylhexanoate;iron(3+) Chemical compound [Fe+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O ULUYRVWYCIOFRV-UHFFFAOYSA-K 0.000 description 1
RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
CDVAIHNNWWJFJW-UHFFFAOYSA-N 3,5-diethoxycarbonyl-1,4-dihydrocollidine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C CDVAIHNNWWJFJW-UHFFFAOYSA-N 0.000 description 1
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 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
RPWFJAMTCNSJKK-UHFFFAOYSA-N Dodecyl gallate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 RPWFJAMTCNSJKK-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
201000008450 Intracranial aneurysm Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
206010067482 No adverse event Diseases 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
GPDWNEFHGANACG-UHFFFAOYSA-L [dibutyl(2-ethylhexanoyloxy)stannyl] 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)O[Sn](CCCC)(CCCC)OC(=O)C(CC)CCCC GPDWNEFHGANACG-UHFFFAOYSA-L 0.000 description 1
210000003815 abdominal wall Anatomy 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000001464 adherent effect Effects 0.000 description 1
150000001334 alicyclic compounds Chemical class 0.000 description 1
150000007824 aliphatic compounds Chemical class 0.000 description 1
230000002009 allergenic effect Effects 0.000 description 1
AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
229940064804 betadine Drugs 0.000 description 1
239000000227 bioadhesive Substances 0.000 description 1
238000006065 biodegradation reaction Methods 0.000 description 1
239000013060 biological fluid Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
230000036760 body temperature Effects 0.000 description 1
239000008366 buffered solution Substances 0.000 description 1
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000008859 change Effects 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
QAEKNCDIHIGLFI-UHFFFAOYSA-L cobalt(2+);2-ethylhexanoate Chemical compound [Co+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QAEKNCDIHIGLFI-UHFFFAOYSA-L 0.000 description 1
239000000805 composite resin Substances 0.000 description 1
210000002808 connective tissue Anatomy 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
238000004132 cross linking 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
230000003247 decreasing effect Effects 0.000 description 1
239000003479 dental cement Substances 0.000 description 1
210000004207 dermis Anatomy 0.000 description 1
238000011161 development Methods 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
235000010386 dodecyl gallate Nutrition 0.000 description 1
230000007515 enzymatic degradation Effects 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
210000003238 esophagus Anatomy 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
210000003195 fascia Anatomy 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000011507 gypsum plaster Substances 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
210000002216 heart Anatomy 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
230000007794 irritation Effects 0.000 description 1
125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 1
210000002414 leg Anatomy 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000017074 necrotic cell death Effects 0.000 description 1
229940105631 nembutal Drugs 0.000 description 1
231100001223 noncarcinogenic Toxicity 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000000399 orthopedic effect Effects 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920001610 polycaprolactone Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920000909 polytetrahydrofuran Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
235000004252 protein component Nutrition 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000003014 reinforcing effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229940083575 sodium dodecyl sulfate Drugs 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
YFPNAQYEHBHHHI-UHFFFAOYSA-M sodium;2,3,4-trichlorophenolate Chemical compound [Na+].[O-]C1=CC=C(Cl)C(Cl)=C1Cl YFPNAQYEHBHHHI-UHFFFAOYSA-M 0.000 description 1
DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
239000001590 sorbitan monolaureate Substances 0.000 description 1
235000011067 sorbitan monolaureate Nutrition 0.000 description 1
235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
239000001570 sorbitan monopalmitate Substances 0.000 description 1
229940031953 sorbitan monopalmitate Drugs 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
229940094938 stannous 2-ethylhexanoate Drugs 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000758 substrate Substances 0.000 description 1
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
210000000689 upper leg Anatomy 0.000 description 1
229960005088 urethane Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 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
- 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
- A61L24/0047—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
- A61L24/0073—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material with a macromolecular matrix
- 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
- 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
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty acids
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6629—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/28—Non-macromolecular organic substances
- C08L2666/40—Phosphorus-containing compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/54—Inorganic substances

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Animal Behavior & Ethology (AREA)
Surgery (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Composite Materials (AREA)
Materials Engineering (AREA)
Engineering & Computer Science (AREA)
Materials For Medical Uses (AREA)
Adhesives Or Adhesive Processes (AREA)
Compositions Of Macromolecular Compounds (AREA)

IL9491090A 1990-06-29 1990-06-29 Biomedical adhesive compositions IL94910A (en)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
IL9491090A IL94910A (en)	1990-06-29	1990-06-29	Biomedical adhesive compositions
US07/722,088 US5266608A (en)	1990-06-29	1991-06-27	Biomedical adhesive compositions
DE69114931T DE69114931T2 (de)	1990-06-29	1991-06-28	Biomedizinische Adhäsivmasse.
EP91401786A EP0466552B1 (de)	1990-06-29	1991-06-28	Biomedizinische Adhäsivmasse
JP3158611A JPH05111530A (ja)	1990-06-29	1991-06-28	生物医学接着剤配合物
CA002045964A CA2045964C (en)	1990-06-29	1991-06-28	Biomedical adhesive compositions

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IL9491090A IL94910A (en)	1990-06-29	1990-06-29	Biomedical adhesive compositions

Publications (2)

Publication Number	Publication Date
IL94910A0 IL94910A0 (en)	1991-04-15
IL94910A true IL94910A (en)	1994-04-12

Family

ID=11061358

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9491090A IL94910A (en)	1990-06-29	1990-06-29	Biomedical adhesive compositions

Country Status (6)

Country	Link
US (1)	US5266608A (de)
EP (1)	EP0466552B1 (de)
JP (1)	JPH05111530A (de)
CA (1)	CA2045964C (de)
DE (1)	DE69114931T2 (de)
IL (1)	IL94910A (de)

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DE19812195C2 (de) *	1998-03-19	2000-03-30	Uwe Storch	Verfahren zur Herstellung eines gewebebildenden Implantats und seine Verwendung
US6165140A (en)	1998-12-28	2000-12-26	Micrus Corporation	Composite guidewire
US6352531B1 (en)	1999-03-24	2002-03-05	Micrus Corporation	Variable stiffness optical fiber shaft
US6887235B2 (en)	1999-03-24	2005-05-03	Micrus Corporation	Variable stiffness heating catheter
US6524327B1 (en) *	2000-09-29	2003-02-25	Praxis, Llc	In-situ bonds
US6468660B2 (en)	2000-12-29	2002-10-22	St. Jude Medical, Inc.	Biocompatible adhesives
MXPA03007665A (es) *	2001-02-26	2004-03-16	Univ Duke	Polimeros dendriticos novedosos y sus usos biomedicos.
US20020173770A1 (en) *	2001-05-16	2002-11-21	Flory Alan R.	Adhesive delivery system
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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
GB0202233D0 (en)	2002-01-31	2002-03-20	Smith & Nephew	Bioresorbable polymers
US7264823B2 (en)	2002-02-08	2007-09-04	University Of Pittsburgh	Medical adhesive and methods of tissue adhesion
US20040131582A1 (en) *	2002-02-26	2004-07-08	Grinstaff Mark W.	Novel dendritic polymers and their biomedical uses
DE10242075B4 (de) *	2002-09-11	2007-02-01	Curasan Ag	Knochenadhäsives Polyurethanpolymer, Verfahren zu seiner Herstellung und seine Verwendungen
AU2003284924B2 (en) *	2002-10-28	2009-01-08	Covidien Lp	Bioabsorbable adhesive compounds
JP2006512427A (ja) *	2002-10-28	2006-04-13	タイコヘルスケアグループエルピー	迅速に硬化する組成物
JP2006516467A (ja)	2003-02-04	2006-07-06	オステオテック，インコーポレイテッド	骨インプラントのためのポリウレタン
US7141354B2 (en) *	2003-09-30	2006-11-28	Dai Nippon Printing Co., Ltd.	Photo radical generator, photo sensitive resin composition and article
GB0329654D0 (en)	2003-12-23	2004-01-28	Smith & Nephew	Tunable segmented polyacetal
WO2005094724A1 (en) *	2004-03-29	2005-10-13	Promethean Surgical Devices Llc	Surgical adhesive formulations and methods of preparation
MXPA06013721A (es) *	2004-05-27	2007-04-17	Univ Pittsburgh	Adhesivo medico y metodos de adhesion de tejido.
RU2442613C2 (ru) *	2006-01-27	2012-02-20	Юниверсити Оф Питтсбург - Оф Дзе Коммонвелс Систем Оф Хайе Эдьюкейнш	Медицинский клей и способы склеивания тканей
AU2007325001B2 (en)	2006-11-30	2014-04-10	Smith & Nephew, Inc.	Fiber reinforced composite material
EP2142353A1 (de) *	2007-04-18	2010-01-13	Smith & Nephew PLC	Expansionsformen von formgedächtnis-polymeren
JP5680957B2 (ja) *	2007-04-19	2015-03-04	スミスアンドネフューインコーポレーテッドＳｍｉｔｈ＆Ｎｅｐｈｅｗ，Ｉｎｃ．	グラフト固定
ATE547129T1 (de)	2007-04-19	2012-03-15	Smith & Nephew Inc	Multimodale formgedächtnis-polymere
US8182647B2 (en)	2007-07-23	2012-05-22	Cohera Medical, Inc.	Hydrophilic biodegradable adhesives
US8287566B2 (en)	2007-10-26	2012-10-16	Cohera Medical, Inc.	Spray devices and methods
US8500947B2 (en)	2007-11-15	2013-08-06	Covidien Lp	Speeding cure rate of bioadhesives
DE102007061506A1 (de) *	2007-12-18	2009-06-25	Henkel Ag & Co. Kgaa	Biologisch abbaubarer Klebstoff
US8668697B2 (en) *	2009-10-07	2014-03-11	Abyrx, Inc.	Methods and devices for sternal closure
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DE3042558A1 (de) *	1980-11-12	1982-06-24	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von kaelteflexiblen, gegebenenfalls zellhaltigen polyurethanelastomeren
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US4557691A (en) *	1983-04-11	1985-12-10	Johnson & Johnson Dental Products Company	Dental porcelain paste and method of using the same
DE3401129A1 (de) *	1984-01-14	1985-07-18	Henkel KGaA, 4000 Düsseldorf	Verfahren zur herstellung gemischter polyurethan-prepolymerer
US4740534A (en) *	1985-08-30	1988-04-26	Sanyo Chemical Industries, Ltd.	Surgical adhesive
US4971800A (en) *	1988-07-08	1990-11-20	The Regents Of The University Of California	Method and compositions for enhancing the cutaneous penetration of pharmacologically active agents
US5051260A (en) *	1987-07-16	1991-09-24	The Regents Of The University Of California	Method and composition for enhancing the cutaneous penetration of pharmacologically active agents
US4804691A (en) *	1987-08-28	1989-02-14	Richards Medical Company	Method for making a biodegradable adhesive for soft living tissue
JP2691722B2 (ja) *	1988-03-07	1997-12-17	旭硝子株式会社	外科用接着剤
US5064653A (en) *	1988-03-29	1991-11-12	Ferris Mfg. Co.	Hydrophilic foam compositions

1990
- 1990-06-29 IL IL9491090A patent/IL94910A/en unknown
1991
- 1991-06-27 US US07/722,088 patent/US5266608A/en not_active Expired - Lifetime
- 1991-06-28 CA CA002045964A patent/CA2045964C/en not_active Expired - Lifetime
- 1991-06-28 JP JP3158611A patent/JPH05111530A/ja active Pending
- 1991-06-28 EP EP91401786A patent/EP0466552B1/de not_active Expired - Lifetime
- 1991-06-28 DE DE69114931T patent/DE69114931T2/de not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE69114931D1 (de)	1996-01-11
US5266608A (en)	1993-11-30
IL94910A0 (en)	1991-04-15
CA2045964A1 (en)	1991-12-30
EP0466552A2 (de)	1992-01-15
JPH05111530A (ja)	1993-05-07
EP0466552A3 (en)	1992-05-06
DE69114931T2 (de)	1996-06-20
CA2045964C (en)	2004-11-30
EP0466552B1 (de)	1995-11-29

Legal Events

Date	Code	Title
1996-10-16	KB	Patent renewed
2000-10-31	KB	Patent renewed
2004-07-25	KB	Patent renewed
2008-11-03	KB	Patent renewed

Publication	Publication Date	Title
US5266608A (en)	1993-11-30	Biomedical adhesive compositions
EP1613679B1 (de)	2011-09-21	Verfahren zur durchführung von knochenwachstumsfördernden medizinischen prozeduren, knochenwachstumsfördernde zusammensetzungen und herstellungsverfahren dafür
US5876743A (en)	1999-03-02	Biocompatible adhesion in tissue repair
EP2753371B1 (de)	2021-08-04	Absorbierbare knochenzemente aus mehreren wachsen und blutstillenden zusammensetzungen und verwendungsverfahren dafür
US4804691A (en)	1989-02-14	Method for making a biodegradable adhesive for soft living tissue
Qiu et al.	2019	Bioadhesives in neurosurgery: a review
US5350798A (en)	1994-09-27	Absorbable tissue adhesives
EP3050579A1 (de)	2016-08-03	Neue klebstoffe für medizinische anwendungen
EP3518995B1 (de)	2023-06-07	Zusammensetzung aus alpha-tcp, silicat und phosphorylierter aminosäure
US20240226370A1 (en)	2024-07-11	Soft tissue adhesive composition of alpha-tcp and phosphorylated amino acid
WO2008046405A2 (de)	2008-04-24	Behandlung von osteoporose
Meyer et al.	1979	Bone bonding through bioadhesives: present status
US20060276562A1 (en)	2006-12-07	Composite materials for bone defect filling and bone replacement
CA3227376A1 (en)	2023-02-09	Nonabsorbable settable multi-putty bone cements, hemostatic compositions and methods of use
JPH07101874A (ja)	1995-04-18	骨修復治療剤
AU2007210055A1 (en)	2007-08-09	Medical adhesive and methods of tissue adhesion
DE10242075B4 (de)	2007-02-01	Knochenadhäsives Polyurethanpolymer, Verfahren zu seiner Herstellung und seine Verwendungen
JPH0363061A (ja)	1991-03-19	医療用接着剤
WO2005092404A1 (ja)	2005-10-06	医療用接着剤
EP0123323B1 (de)	1989-08-23	Verwendung von difunktionellen Acrylsäure- und Methacrylsäureestern zur Herstellung von härtbaren Knochenzementen
EP4537861A1 (de)	2025-04-16	Biokompatible polyurethanmatrix
Vainio	1978	Non-metallic fixatives in orthopedic surgery: some aspects of their present and future properties
Mun et al.	2023	Biomedical Adhesives
Brandeis et al.	1993	A new bioadhesive for in vivo bone adhesion
DD268130A3 (de)	1989-05-24	Verwendung einer bioaktiven Polymer-Mineral-Mischung