CA2320786C - Electron beam sterilization of liquid adhesive compositions - Google Patents
Electron beam sterilization of liquid adhesive compositions Download PDFInfo
- Publication number
- CA2320786C CA2320786C CA002320786A CA2320786A CA2320786C CA 2320786 C CA2320786 C CA 2320786C CA 002320786 A CA002320786 A CA 002320786A CA 2320786 A CA2320786 A CA 2320786A CA 2320786 C CA2320786 C CA 2320786C
- Authority
- CA
- Canada
- Prior art keywords
- acid
- container
- electron beam
- composition
- irradiation
- 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.)
- Expired - Fee Related
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- 239000000203 mixture Substances 0.000 title claims abstract description 72
- 238000010894 electron beam technology Methods 0.000 title claims abstract description 31
- 239000000853 adhesive Substances 0.000 title claims abstract description 23
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 23
- 239000007788 liquid Substances 0.000 title claims abstract description 22
- 230000001954 sterilising effect Effects 0.000 title claims abstract description 20
- 238000004659 sterilization and disinfection Methods 0.000 title claims description 11
- 238000000034 method Methods 0.000 claims abstract description 41
- -1 1,1-disubstituted ethylene Chemical group 0.000 claims description 47
- 239000000178 monomer Substances 0.000 claims description 38
- 239000003381 stabilizer Substances 0.000 claims description 24
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 229920001577 copolymer Polymers 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 7
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
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- 235000019282 butylated hydroxyanisole Nutrition 0.000 claims description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004255 Butylated hydroxyanisole Substances 0.000 claims description 4
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- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 4
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims description 4
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- JJJFUHOGVZWXNQ-UHFFFAOYSA-N enbucrilate Chemical compound CCCCOC(=O)C(=C)C#N JJJFUHOGVZWXNQ-UHFFFAOYSA-N 0.000 claims description 3
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- 230000000977 initiatory effect Effects 0.000 claims description 3
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 2
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- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims 1
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- RPQUGMLCZLGZTG-UHFFFAOYSA-N octyl cyanoacrylate Chemical group CCCCCCCCOC(=O)C(=C)C#N RPQUGMLCZLGZTG-UHFFFAOYSA-N 0.000 claims 1
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- 125000000217 alkyl group Chemical group 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
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- 239000003795 chemical substances by application Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
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- 150000001875 compounds Chemical class 0.000 description 10
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- 125000001183 hydrocarbyl group Chemical group 0.000 description 8
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- 239000000463 material Substances 0.000 description 7
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- 239000003638 chemical reducing agent Substances 0.000 description 6
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- 230000035515 penetration Effects 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- CQVWXNBVRLKXPE-UHFFFAOYSA-N 2-octyl cyanoacrylate Chemical compound CCCCCCC(C)OC(=O)C(=C)C#N CQVWXNBVRLKXPE-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
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- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 210000001724 microfibril Anatomy 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 108010035532 Collagen Proteins 0.000 description 3
- 102000008186 Collagen Human genes 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 229920001213 Polysorbate 20 Polymers 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 206010052428 Wound Diseases 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 229920001436 collagen Polymers 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- OCOCSIDEWXUOQN-UHFFFAOYSA-N 2-cyanopenta-2,4-dienoic acid Chemical class OC(=O)C(C#N)=CC=C OCOCSIDEWXUOQN-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical class [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 2
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 2
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- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229920002627 poly(phosphazenes) Polymers 0.000 description 1
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- 150000008117 polysulfides Polymers 0.000 description 1
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 229960000776 sodium tetradecyl sulfate Drugs 0.000 description 1
- OZWUZVBLUVAWMT-UHFFFAOYSA-N sodium;2-(3-hydroxy-2,4,5,7-tetraiodo-6-oxoxanthen-9-yl)benzoic acid Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C(O)=C(I)C=C21 OZWUZVBLUVAWMT-UHFFFAOYSA-N 0.000 description 1
- UPUIQOIQVMNQAP-UHFFFAOYSA-M sodium;tetradecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCOS([O-])(=O)=O UPUIQOIQVMNQAP-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 235000019710 soybean protein Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
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- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
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- 229940033123 tannic acid Drugs 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- 229940075469 tissue adhesives Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
- JNXDCMUUZNIWPQ-UHFFFAOYSA-N trioctyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)=C1 JNXDCMUUZNIWPQ-UHFFFAOYSA-N 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/02—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using physical phenomena
- A61L2/08—Radiation
- A61L2/087—Particle radiation, e.g. electron-beam, alpha or beta radiation
-
- 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
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/02—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using physical phenomena
- A61L2/08—Radiation
-
- 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
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/02—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using physical phenomena
- A61L2/08—Radiation
- A61L2/081—Gamma radiation
-
- 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
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/02—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using physical phenomena
- A61L2/08—Radiation
- A61L2/12—Microwaves
-
- 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
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
- A61L2/20—Gaseous substances, e.g. vapours
-
- 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
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
- A61L2/20—Gaseous substances, e.g. vapours
- A61L2/206—Ethylene oxide
-
- 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
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
- A61L2/20—Gaseous substances, e.g. vapours
- A61L2/208—Hydrogen peroxide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L35/04—Homopolymers or copolymers of nitriles
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Materials For Medical Uses (AREA)
- Apparatus For Disinfection Or Sterilisation (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/025,472 | 1998-02-18 | ||
| US09/025,472 US6143805A (en) | 1998-02-18 | 1998-02-18 | Electron beam sterilization of liquid adhesive compositions |
| PCT/US1999/000992 WO1999042142A1 (en) | 1998-02-18 | 1999-01-19 | Electron beam sterilization of liquid adhesive compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2320786A1 CA2320786A1 (en) | 1999-08-26 |
| CA2320786C true CA2320786C (en) | 2004-08-10 |
Family
ID=21826262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002320786A Expired - Fee Related CA2320786C (en) | 1998-02-18 | 1999-01-19 | Electron beam sterilization of liquid adhesive compositions |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6143805A (en:Method) |
| EP (1) | EP1056480B1 (en:Method) |
| JP (1) | JP3667636B2 (en:Method) |
| CN (1) | CN1297360A (en:Method) |
| AT (1) | ATE265864T1 (en:Method) |
| AU (1) | AU735362B2 (en:Method) |
| BR (1) | BR9908080A (en:Method) |
| CA (1) | CA2320786C (en:Method) |
| DE (1) | DE69917002T2 (en:Method) |
| WO (1) | WO1999042142A1 (en:Method) |
Families Citing this family (86)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5762955A (en) | 1994-02-04 | 1998-06-09 | Smith; Stephen Jay | Method for application and maintenance of medication on body tissue |
| US20020018689A1 (en) * | 1995-06-07 | 2002-02-14 | Badejo Ibraheem T. | Adhesive applicators with improved polymerization initiators |
| EP1161384A1 (en) * | 1998-09-01 | 2001-12-12 | Closure Medical Corporation | Package assembly with applicator and container for adhesive materials |
| JP4249395B2 (ja) * | 1998-09-18 | 2009-04-02 | メドロジック グローバル リミテッド | シアノアクリル酸エステル組成物を無菌化する方法 |
| GB9820457D0 (en) | 1998-09-18 | 1998-11-11 | Medlogic Global Corp | Methods for sterilizing cyanoacrylate compositions |
| US6310166B1 (en) * | 1999-08-12 | 2001-10-30 | Closure Medical Corporation | Sterilized cyanoacrylate solutions containing thickeners |
| WO2001023007A1 (en) * | 1999-09-24 | 2001-04-05 | Iotron Industries Canada Inc. | Electron beam sterilization of contained liquids |
| US6579469B1 (en) * | 1999-10-29 | 2003-06-17 | Closure Medical Corporation | Cyanoacrylate solutions containing preservatives |
| US6183593B1 (en) * | 1999-12-23 | 2001-02-06 | Closure Medical Corporation | 1,1-disubstituted ethylene adhesive compositions containing polydimethylsiloxane |
| US6698162B2 (en) * | 2000-03-23 | 2004-03-02 | Teikoku Pharma Usa, Inc. | Methods of producing a terminally sterilized topical patch preparation |
| US6620846B1 (en) * | 2000-08-02 | 2003-09-16 | Closure Medical Corporation | Absorbable adhesive compositions |
| US6492573B1 (en) * | 2000-08-17 | 2002-12-10 | Arthur Ashman | Biocompatible oral bandage, application and method of manufacture |
| US6607631B1 (en) | 2000-09-08 | 2003-08-19 | Closure Medical Corporation | Adhesive compositions with reduced coefficient of friction |
| US6605667B1 (en) * | 2000-09-08 | 2003-08-12 | Closure Medical Corporation | Antioxidant enriched adhesive compositions and storage containers therefor |
| EP1345972A4 (en) * | 2000-11-21 | 2005-03-09 | Medlogic Global Ltd | PROCESS FOR STERILIZING CYANOACRYLATE COMPOSITIONS |
| US6579916B1 (en) | 2000-11-21 | 2003-06-17 | Medlogic Global Corporation | Methods for sterilizing cyanoacrylate compositions |
| US6616019B2 (en) * | 2001-07-18 | 2003-09-09 | Closure Medical Corporation | Adhesive applicator with improved applicator tip |
| US6811341B2 (en) | 2001-08-16 | 2004-11-02 | Closure Medical Corporation | Multiple-component combining |
| US6547467B2 (en) | 2001-08-29 | 2003-04-15 | Closure Medical Corporation | Microapplicators, delivery systems and methods for adhesives and sealants |
| US6849082B2 (en) | 2001-10-19 | 2005-02-01 | Spartan Products Inc. | Method for curing cyanoacrylate adhesives |
| US7255874B1 (en) | 2001-12-21 | 2007-08-14 | Closure Medical Corporation | Biocompatible polymers and adhesives: compositions, methods of making and uses related thereto |
| AU2003211107A1 (en) * | 2002-02-20 | 2003-09-09 | Spartan Producs Inc. | Method for curing cyanoacrylate adhesives |
| US20030158579A1 (en) | 2002-02-20 | 2003-08-21 | Max Azevedo | Method for curing cyanoacrylate adhesives |
| US20030183801A1 (en) * | 2002-03-28 | 2003-10-02 | Hu Yang | Porous oxygen scavenging material |
| US7371345B2 (en) * | 2002-12-23 | 2008-05-13 | Closure Medical Corporation | Sterilization of medical adhesive kits |
| US20040151688A1 (en) * | 2003-01-31 | 2004-08-05 | Closure Medical Corporation | Adhesive treatment for epistaxis |
| CA2457248C (en) | 2003-02-07 | 2012-07-17 | Closure Medical Corporation | Applicators, dispensers and methods for dispensing and applying adhesive material |
| US20040223932A1 (en) * | 2003-05-05 | 2004-11-11 | Closure Medical Corporation | Adhesive treatment for acne |
| US20040223946A1 (en) * | 2003-05-05 | 2004-11-11 | Closure Medical Corporation | Adhesive treatment for insect and related bites |
| US20050042266A1 (en) * | 2003-08-21 | 2005-02-24 | Closure Medical Corporation | Cyanoacrylate compositions containing anti-microbial agent |
| US20050197421A1 (en) * | 2004-03-03 | 2005-09-08 | Loomis Gary L. | Process for preparation of cyanoacrylate compositions |
| US20050196376A1 (en) * | 2004-03-03 | 2005-09-08 | G. L. Loomis & Associates, Inc. | Preparation of polymerizable compositions |
| US20060030808A1 (en) * | 2004-08-09 | 2006-02-09 | Aso Corporation | Liquid bandage and tissue sealant |
| US20060045897A1 (en) * | 2004-08-27 | 2006-03-02 | Aso Corporation | Occlusive articles for wart treatment |
| US20060093572A1 (en) * | 2004-11-03 | 2006-05-04 | Bordoloi Binoy K | Cyanoacrylate monomer formulation containing diiodomethyl-p-tolylsulfone and 2,4,4'-trichloro-2' -hydroxydiphenyl ether |
| DE602006006798D1 (de) * | 2005-01-14 | 2009-06-25 | Henkel Ag & Co Kgaa | Röntgendichte cyanoacrylat-zusammensetzungen |
| CA2619886C (en) | 2005-08-17 | 2016-01-19 | Ann Beal Salamone | Conformable solvent-based bandage and coating material |
| EP1968655B1 (en) * | 2005-12-07 | 2011-03-02 | Rochal Industries, LLP | Conformable bandage and coating material |
| US20070248486A1 (en) * | 2006-04-24 | 2007-10-25 | Clast Trading Ltd | Process for Sterilization of Cyanoacrylate Adhesive Compositions and Devices |
| DE102006027305B4 (de) | 2006-06-06 | 2016-12-22 | Aesculap Ag | Verfahren zur Sterilisation einer gasdurchlässigen und keimdichten Verpackung |
| US7772306B2 (en) * | 2006-07-18 | 2010-08-10 | Glustitch, Inc. | Cyanoacrylate compositions having increased stability under irradiation |
| US8603138B2 (en) | 2006-10-04 | 2013-12-10 | Ethicon Endo-Surgery, Inc. | Use of an adhesive to treat intraluminal bleeding |
| US7914511B2 (en) | 2006-10-18 | 2011-03-29 | Ethicon Endo-Surgery, Inc. | Use of biosurgical adhesive as bulking agent |
| US7749235B2 (en) | 2006-10-20 | 2010-07-06 | Ethicon Endo-Surgery, Inc. | Stomach invagination method and apparatus |
| US7441973B2 (en) | 2006-10-20 | 2008-10-28 | Ethicon Endo-Surgery, Inc. | Adhesive applicator |
| US7658305B2 (en) | 2006-10-25 | 2010-02-09 | Ethicon Endo-Surgery, Inc. | Adhesive applier with articulating tip |
| US8876844B2 (en) | 2006-11-01 | 2014-11-04 | Ethicon Endo-Surgery, Inc. | Anastomosis reinforcement using biosurgical adhesive and device |
| US7892250B2 (en) | 2006-11-01 | 2011-02-22 | Ethicon Endo-Surgery, Inc. | Use of biosurgical adhesive on inflatable device for gastric restriction |
| US7833216B2 (en) | 2006-11-08 | 2010-11-16 | Ethicon Endo-Surgery, Inc. | Fluid plunger adhesive dispenser |
| US8118508B2 (en) * | 2006-11-30 | 2012-02-21 | Closure Medical Corporation | Dispenser with a frangible container and a rotating breaking member, for dispensing a polymerizable monomer adhesive |
| EP1967213B1 (de) * | 2007-03-05 | 2014-02-26 | NOBA Verbandmittel Danz GmbH u. Co. KG | Verfahren zur Herstellung eines Verbandstoffes |
| US8376013B2 (en) | 2008-03-11 | 2013-02-19 | Duke University | Plasmonic assisted systems and methods for interior energy-activation from an exterior source |
| US20080302827A1 (en) * | 2007-06-06 | 2008-12-11 | Gerrish Donald L | Spray dispenser |
| US8729121B2 (en) | 2007-06-25 | 2014-05-20 | Adhezion Biomedical, Llc | Curing accelerator and method of making |
| EP2205497A4 (en) * | 2007-09-06 | 2012-10-24 | Suremilk Llc | UNIVERSAL DRINKING ADAPTER FOR DRINKING BOTTLES FOR LIQUID CONSUMPTION AND DEVICES AND DEVICES FOR DETERMINING SMALL MOLECULES, METAL IONS, ENDOTOXINS AND BACTERIA IN MILK, AND METHODS OF USE THEREOF |
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1998
- 1998-02-18 US US09/025,472 patent/US6143805A/en not_active Expired - Lifetime
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1999
- 1999-01-19 AT AT99903147T patent/ATE265864T1/de not_active IP Right Cessation
- 1999-01-19 CA CA002320786A patent/CA2320786C/en not_active Expired - Fee Related
- 1999-01-19 JP JP2000532155A patent/JP3667636B2/ja not_active Expired - Fee Related
- 1999-01-19 BR BR9908080-0A patent/BR9908080A/pt not_active IP Right Cessation
- 1999-01-19 EP EP99903147A patent/EP1056480B1/en not_active Expired - Lifetime
- 1999-01-19 WO PCT/US1999/000992 patent/WO1999042142A1/en not_active Ceased
- 1999-01-19 CN CN99805096A patent/CN1297360A/zh active Pending
- 1999-01-19 DE DE69917002T patent/DE69917002T2/de not_active Expired - Lifetime
- 1999-01-19 AU AU23235/99A patent/AU735362B2/en not_active Ceased
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|---|---|
| JP3667636B2 (ja) | 2005-07-06 |
| EP1056480A1 (en) | 2000-12-06 |
| EP1056480B1 (en) | 2004-05-06 |
| DE69917002T2 (de) | 2005-05-04 |
| AU2323599A (en) | 1999-09-06 |
| US6143805A (en) | 2000-11-07 |
| JP2002503522A (ja) | 2002-02-05 |
| WO1999042142A1 (en) | 1999-08-26 |
| BR9908080A (pt) | 2000-10-31 |
| AU735362B2 (en) | 2001-07-05 |
| CA2320786A1 (en) | 1999-08-26 |
| DE69917002D1 (de) | 2004-06-09 |
| CN1297360A (zh) | 2001-05-30 |
| ATE265864T1 (de) | 2004-05-15 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
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