DE69403358T2 - Quaternäre Ammoniumgruppen-enthaltende antimikrobielle Polymere, Zusammensetzungen auf Basis dieser Polymere und Monomere für ihre Herstellung - Google Patents
Quaternäre Ammoniumgruppen-enthaltende antimikrobielle Polymere, Zusammensetzungen auf Basis dieser Polymere und Monomere für ihre HerstellungInfo
- Publication number
- DE69403358T2 DE69403358T2 DE69403358T DE69403358T DE69403358T2 DE 69403358 T2 DE69403358 T2 DE 69403358T2 DE 69403358 T DE69403358 T DE 69403358T DE 69403358 T DE69403358 T DE 69403358T DE 69403358 T2 DE69403358 T2 DE 69403358T2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- antimicrobial
- groups
- alkyl
- quaternary ammonium
- 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
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 44
- 229920000642 polymer Polymers 0.000 title claims abstract description 44
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims abstract description 31
- 239000000203 mixture Substances 0.000 title claims description 17
- 229920002118 antimicrobial polymer Polymers 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 230000000845 anti-microbial effect Effects 0.000 claims abstract description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 17
- -1 vinyl amines Chemical class 0.000 claims description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 229920001577 copolymer Polymers 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 230000000249 desinfective effect Effects 0.000 claims description 8
- 238000004140 cleaning Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000004599 antimicrobial Substances 0.000 claims description 5
- 239000003431 cross linking reagent Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229920001519 homopolymer Polymers 0.000 claims description 5
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical class C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003926 acrylamides Chemical class 0.000 claims description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 2
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002997 ophthalmic solution Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- OZFIGURLAJSLIR-UHFFFAOYSA-N 1-ethenyl-2h-pyridine Chemical compound C=CN1CC=CC=C1 OZFIGURLAJSLIR-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims 1
- 229940054534 ophthalmic solution Drugs 0.000 claims 1
- 239000000645 desinfectant Substances 0.000 abstract description 12
- UPXXJZVKYRGUNU-UHFFFAOYSA-M dimethyl-[1-(2-methylprop-2-enoyloxy)henicosan-4-yl]-[3-[methyl(trimethylsilyloxy)silyl]propyl]azanium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC(CCCOC(=O)C(C)=C)[N+](C)(C)CCC[SiH](C)O[Si](C)(C)C UPXXJZVKYRGUNU-UHFFFAOYSA-M 0.000 abstract description 6
- 229920001558 organosilicon polymer Polymers 0.000 abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical class OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000017 hydrogel Substances 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- BVWUEIUNONATML-UHFFFAOYSA-N n-benzylethenamine Chemical compound C=CNCC1=CC=CC=C1 BVWUEIUNONATML-UHFFFAOYSA-N 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000012466 permeate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 231100001231 less toxic Toxicity 0.000 description 2
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 2
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 2
- 150000003961 organosilicon compounds Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 1
- FTLTTYGQIYQDEL-UHFFFAOYSA-N 1,1-bis(ethenyl)urea Chemical compound NC(=O)N(C=C)C=C FTLTTYGQIYQDEL-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- NEBBLNDVSSWJLL-UHFFFAOYSA-N 2,3-bis(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(OC(=O)C(C)=C)COC(=O)C(C)=C NEBBLNDVSSWJLL-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 1
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
- KAUVYPZCBVZESR-UHFFFAOYSA-N 2-methylidene-4-oxo-4-prop-2-enoxybutanoic acid Chemical compound OC(=O)C(=C)CC(=O)OCC=C KAUVYPZCBVZESR-UHFFFAOYSA-N 0.000 description 1
- ROHTVIURAJBDES-UHFFFAOYSA-N 2-n,2-n-bis(prop-2-enyl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N(CC=C)CC=C)=N1 ROHTVIURAJBDES-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SLJJEYCPTRKHFI-UHFFFAOYSA-N 3-[6-(2,5-dioxopyrrol-3-yl)hexyl]pyrrole-2,5-dione Chemical compound O=C1NC(=O)C(CCCCCCC=2C(NC(=O)C=2)=O)=C1 SLJJEYCPTRKHFI-UHFFFAOYSA-N 0.000 description 1
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- DFACZWMAJBYXEY-UHFFFAOYSA-N 4-[[dimethyl-[4-(2-methylprop-2-enoyloxy)butyl]silyl]oxy-dimethylsilyl]butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCC[Si](C)(C)O[Si](C)(C)CCCCOC(=O)C(C)=C DFACZWMAJBYXEY-UHFFFAOYSA-N 0.000 description 1
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- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- HABAXTXIECRCKH-UHFFFAOYSA-N bis(prop-2-enyl) butanedioate Chemical compound C=CCOC(=O)CCC(=O)OCC=C HABAXTXIECRCKH-UHFFFAOYSA-N 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
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- 229920006037 cross link polymer Polymers 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- VVYDVQWJZWRVPE-UHFFFAOYSA-L dimethyltin(2+);diiodide Chemical compound C[Sn](C)(I)I VVYDVQWJZWRVPE-UHFFFAOYSA-L 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
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- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
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- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
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- 229940015043 glyoxal Drugs 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
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- 235000006408 oxalic acid Nutrition 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
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- 244000052769 pathogen Species 0.000 description 1
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- 239000000825 pharmaceutical preparation Substances 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
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- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 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 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
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- 229960000834 vinyl ether Drugs 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- 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
- A61L2/18—Liquid substances or solutions comprising solids or dissolved gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Optics & Photonics (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Epidemiology (AREA)
- General Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Eyeglasses (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymerisation Methods In General (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Silicon Polymers (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1737493A | 1993-02-09 | 1993-02-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69403358D1 DE69403358D1 (de) | 1997-07-03 |
| DE69403358T2 true DE69403358T2 (de) | 1997-12-18 |
Family
ID=21782226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69403358T Expired - Fee Related DE69403358T2 (de) | 1993-02-09 | 1994-02-01 | Quaternäre Ammoniumgruppen-enthaltende antimikrobielle Polymere, Zusammensetzungen auf Basis dieser Polymere und Monomere für ihre Herstellung |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US5358688A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0611782B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP3502140B2 (cg-RX-API-DMAC10.html) |
| AT (1) | ATE153679T1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU676238B2 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2115121A1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE69403358T2 (cg-RX-API-DMAC10.html) |
| DK (1) | DK0611782T3 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2102795T3 (cg-RX-API-DMAC10.html) |
| FI (1) | FI940558A7 (cg-RX-API-DMAC10.html) |
| GR (1) | GR3024439T3 (cg-RX-API-DMAC10.html) |
| HK (1) | HK1005743A1 (cg-RX-API-DMAC10.html) |
| IL (1) | IL108540A (cg-RX-API-DMAC10.html) |
| MX (1) | MX9400946A (cg-RX-API-DMAC10.html) |
| NO (1) | NO940421L (cg-RX-API-DMAC10.html) |
| NZ (1) | NZ250832A (cg-RX-API-DMAC10.html) |
| TW (1) | TW243455B (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA94844B (cg-RX-API-DMAC10.html) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5340583A (en) * | 1993-05-06 | 1994-08-23 | Allergan, Inc. | Antimicrobial lenses and lens care systems |
| TW325481B (en) * | 1994-12-05 | 1998-01-21 | Novartis Ag | Silicon-containing polymer having oxygen permeability suitable for ophthalmic applications |
| US6034129A (en) | 1996-06-24 | 2000-03-07 | Geltex Pharmaceuticals, Inc. | Ionic polymers as anti-infective agents |
| JP3989054B2 (ja) * | 1996-07-29 | 2007-10-10 | 株式会社メニコン | コンタクトレンズ用洗浄材 |
| US5843186A (en) * | 1996-12-20 | 1998-12-01 | Implemed, Inc. | Intraocular lens with antimicrobial activity |
| US6290947B1 (en) | 1997-09-19 | 2001-09-18 | Geltex Pharmaceuticals, Inc. | Ionic polymers as toxin-binding agents |
| US6482402B1 (en) | 1999-05-13 | 2002-11-19 | Geltex Pharmaceuticals, Inc. | Antimicrobial compositions and methods |
| US20050065284A1 (en) * | 1999-08-06 | 2005-03-24 | Venkataram Krishnan | Novel latex compositions for deposition on various substrates |
| JP4524838B2 (ja) * | 2000-02-07 | 2010-08-18 | 東レ株式会社 | 眼用レンズ |
| WO2003027123A1 (fr) * | 2000-02-07 | 2003-04-03 | Johnson & Johnson Vision Care, Inc. | Monomeres, polymeres et lentilles ophtalmologiques |
| US20020051754A1 (en) * | 2000-04-13 | 2002-05-02 | Schroeder Joseph D. | Anti-microbial packaging polymer and its method of use |
| US7459167B1 (en) | 2000-07-27 | 2008-12-02 | 3M Innovative Properties Company | Biocidal polyurethane compositions and methods of use |
| US20040151755A1 (en) * | 2000-12-21 | 2004-08-05 | Osman Rathore | Antimicrobial lenses displaying extended efficacy, processes to prepare them and methods of their use |
| US7402318B2 (en) * | 2001-11-14 | 2008-07-22 | Novartis Ag | Medical devices having antimicrobial coatings thereon |
| DE10205923A1 (de) * | 2002-02-12 | 2003-08-21 | Creavis Tech & Innovation Gmbh | Wasch- und Reinigungsformulierungen mit antimikrobiellen Polymeren |
| US8172395B2 (en) | 2002-12-03 | 2012-05-08 | Novartis Ag | Medical devices having antimicrobial coatings thereon |
| US20040151919A1 (en) * | 2003-01-31 | 2004-08-05 | Kimberly-Clark Worldwide, Inc. | Glove having reduced microbe affinity and transmission |
| US7781498B2 (en) | 2003-07-03 | 2010-08-24 | Mallard Creek Polymers, Inc. | Cationic latex as a carrier for bioactive ingredients and methods for making and using the same |
| US7491753B2 (en) | 2003-07-03 | 2009-02-17 | Mallard Creek Polymers, Inc. | Antimicrobial and antistatic polymers and methods of using such polymers on various substrates |
| US7981946B2 (en) | 2003-07-03 | 2011-07-19 | Mallard Creek Polymers, Inc. | Antimicrobial and antistatic polymers and methods of using such polymers on various substrates |
| DE102004036717A1 (de) * | 2004-07-29 | 2006-03-23 | Wacker Chemie Ag | Polyquaternäre Organosiliciumverbindungen enthaltende Zusammensetzungen |
| MX2007011771A (es) * | 2005-03-22 | 2008-03-14 | Biosafe Inc | Metodo para crear un agente antimicrobiano polimerico de amonio cuaternario que contiene silicio libre de solventes, el cual tiene propiedades antimicrobianas superiores sostenidas. |
| US20070048249A1 (en) | 2005-08-24 | 2007-03-01 | Purdue Research Foundation | Hydrophilized bactericidal polymers |
| US7759408B2 (en) * | 2005-12-21 | 2010-07-20 | Bausch & Lomb Incorporated | Silicon-containing monomers end-capped with polymerizable cationic hydrophilic groups |
| US7622512B2 (en) * | 2005-12-21 | 2009-11-24 | Bausch & Lomb Incorporated | Cationic hydrophilic siloxanyl monomers |
| US20070161769A1 (en) * | 2006-01-06 | 2007-07-12 | Schorzman Derek A | Polymerizable silicon-containing monomer bearing pendant cationic hydrophilic groups |
| US7960447B2 (en) * | 2006-04-13 | 2011-06-14 | Bausch & Lomb Incorporated | Cationic end-capped siloxane prepolymer for reduced cross-link density |
| ATE449590T1 (de) * | 2006-04-28 | 2009-12-15 | Ivoclar Vivadent Ag | Dentalwerkstoffe auf der basis radikalisch polymerisierbarer makromere mit antimikrobieller wirkung |
| US7468397B2 (en) * | 2006-06-30 | 2008-12-23 | Bausch & Lomb Incorporated | Polymerizable siloxane-quaternary amine copolymers |
| US20080207774A1 (en) * | 2006-08-24 | 2008-08-28 | Venkataram Krishnan | Anionic latex as a carrier for active ingredients and methods for making and using the same |
| JP5378217B2 (ja) | 2006-08-24 | 2013-12-25 | マラード クリーク ポリマーズ，インコーポレーテッド | 生物活性成分用の担体としてのアニオン性ラテックスならびにその製造方法および使用方法 |
| US20080233062A1 (en) * | 2006-08-24 | 2008-09-25 | Venkataram Krishnan | Cationic latex as a carrier for active ingredients and methods for making and using the same |
| RU2444541C2 (ru) | 2006-08-24 | 2012-03-10 | Маллард Крик Полимерс, Инк. | Катионный латекс в качестве носителя биоактивных ингредиентов и способы его получения и использования |
| JP4899757B2 (ja) * | 2006-09-29 | 2012-03-21 | 東レ株式会社 | 眼用レンズ |
| US20080181931A1 (en) | 2007-01-31 | 2008-07-31 | Yongxing Qiu | Antimicrobial medical devices including silver nanoparticles |
| KR101545757B1 (ko) | 2007-02-26 | 2015-08-19 | 노파르티스 아게 | 하이드로겔 콘택트 렌즈의 제조 방법 |
| US8652499B2 (en) * | 2008-03-10 | 2014-02-18 | Toray Industries, Inc. | Medical antimicrobial composition and medical device comprising the same |
| JP6010807B2 (ja) * | 2011-02-01 | 2016-10-19 | ディーエスエム アイピー アセッツ ビー．ブイ． | 親水性末端基を持つシリコーン含有モノマー |
| EP2489344B1 (de) | 2011-02-15 | 2021-03-24 | Ivoclar Vivadent AG | Dentalwerkstoff auf der Basis einer antimikrobiell wirksamen Verbindung |
| WO2014118339A1 (de) | 2013-01-31 | 2014-08-07 | Fachhochschule Münster | Antimikrobielles polymer |
| USRE49528E1 (en) | 2013-04-26 | 2023-05-16 | Biointeractions Ltd. | Bioactive coatings |
| ES3047457T3 (en) | 2013-04-26 | 2025-12-03 | Biointeractions Ltd | Bioactive coatings |
| EP3583176B1 (en) * | 2017-02-16 | 2020-12-16 | Momentive Performance Materials Inc. | Ionically modified silicones, compositions, and medical devices formed therefrom |
| WO2018222622A1 (en) | 2017-05-27 | 2018-12-06 | Poly Group LLC | Dispersible antimicrobial complex and coatings therefrom |
| EP3638740B1 (en) | 2017-06-16 | 2024-08-07 | Poly Group LLC | Polymeric antimicrobial surfactant |
| EP3431171A1 (en) * | 2017-07-19 | 2019-01-23 | Gambro Lundia AB | Filter membrane and device |
| EP3745998A4 (en) * | 2018-01-31 | 2021-09-01 | KeraMed, Inc. | ANTIMICROBIAL POLYMER FOR USE IN OPHTHALMIC IMPLANTS |
| JP6958511B2 (ja) * | 2018-08-17 | 2021-11-02 | 信越化学工業株式会社 | オルガノポリシロキサン化合物およびその製造方法並びにそれを含有する帯電防止剤および硬化性組成物 |
| AU2019360154B2 (en) | 2018-10-18 | 2025-04-03 | Topikos Scientific, Inc. | Organosilanes for the treatment of infections |
| JP7211274B2 (ja) * | 2019-06-18 | 2023-01-24 | 信越化学工業株式会社 | 撥水剤組成物 |
| CN114901291A (zh) | 2019-10-18 | 2022-08-12 | 托皮科斯药品公司 | 抗菌有机硅烷 |
| US11697694B2 (en) * | 2020-05-29 | 2023-07-11 | Gc Corporation | Method of manufacturing polymerizable composition, polymerizable composition, and cured product |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2976576A (en) * | 1956-04-24 | 1961-03-28 | Wichterle Otto | Process for producing shaped articles from three-dimensional hydrophilic high polymers |
| CH461106A (de) * | 1965-05-24 | 1968-08-15 | Ceskoslovenska Akademie Ved | Verfahren zur Herstellung von Gegenständen aus Hydrogelen durch Polymerisationsguss |
| US3503942A (en) * | 1965-10-23 | 1970-03-31 | Maurice Seiderman | Hydrophilic plastic contact lens |
| US3884886A (en) * | 1973-01-15 | 1975-05-20 | Dow Corning | Cationic unsaturated amine-functional silane coupling agents |
| WO1980002840A1 (en) * | 1979-06-20 | 1980-12-24 | W Foley | Contact lenses with polymer bound asepticizing agents |
| US4482680A (en) * | 1981-09-15 | 1984-11-13 | Dynapol | Quaternary ammonium group-containing polymers having antimicrobial activity |
| US4615882A (en) * | 1982-09-27 | 1986-10-07 | Stockel Richard F | Disinfectant solution for contact lens |
| JPH0625228B2 (ja) * | 1986-10-07 | 1994-04-06 | 富士ゼロックス株式会社 | ケイ素含有ビニル重合体の製造方法 |
| US5326841A (en) * | 1989-01-25 | 1994-07-05 | Epitope, Inc. | Germicidal barriers |
| US5237082A (en) * | 1989-09-22 | 1993-08-17 | Minnesota Mining And Manufacturing Company | Radiation-curable silicone elastomers and pressure sensitive adhesives |
| US5145643A (en) * | 1990-01-05 | 1992-09-08 | Allergan, Inc. | Nonoxidative ophthalmic compositions and methods for preserving and using same |
| CA2041871C (en) * | 1990-05-09 | 2000-07-11 | Ruth A. Rosenthal | Contact lens cleaning and disinfecting with combinations of polymeric quaternary ammonium compounds and enzymes |
| US5200488A (en) * | 1990-11-06 | 1993-04-06 | Sagami Chemical Research Center | Polyorganosiloxane having a quaternary salt at its one terminal and percutaneous absorption-promoting agent |
| US5461173A (en) * | 1993-12-27 | 1995-10-24 | Shin-Etsu Chemical Co., Ltd. | Fluorine-containing organosilicon compound and its manufacture |
| ES2217262T3 (es) * | 1993-12-29 | 2004-11-01 | Syngenta Participations Ag | Derivados de acido vinil-carboxilico. |
| US5399737A (en) * | 1994-04-04 | 1995-03-21 | Alcon Laboratories, Inc. | Quaternary ammonium siloxane compounds and methods for their use |
-
1993
- 1993-05-28 TW TW082104239A patent/TW243455B/zh active
- 1993-11-16 US US08/152,888 patent/US5358688A/en not_active Expired - Lifetime
-
1994
- 1994-02-01 ES ES94810051T patent/ES2102795T3/es not_active Expired - Lifetime
- 1994-02-01 EP EP94810051A patent/EP0611782B1/en not_active Expired - Lifetime
- 1994-02-01 DE DE69403358T patent/DE69403358T2/de not_active Expired - Fee Related
- 1994-02-01 DK DK94810051.6T patent/DK0611782T3/da active
- 1994-02-01 AT AT94810051T patent/ATE153679T1/de active
- 1994-02-03 JP JP01161794A patent/JP3502140B2/ja not_active Expired - Fee Related
- 1994-02-03 IL IL10854094A patent/IL108540A/en not_active IP Right Cessation
- 1994-02-04 AU AU54918/94A patent/AU676238B2/en not_active Ceased
- 1994-02-07 FI FI940558A patent/FI940558A7/fi unknown
- 1994-02-07 MX MX9400946A patent/MX9400946A/es not_active IP Right Cessation
- 1994-02-07 NZ NZ250832A patent/NZ250832A/en unknown
- 1994-02-07 CA CA002115121A patent/CA2115121A1/en not_active Abandoned
- 1994-02-08 ZA ZA94844A patent/ZA94844B/xx unknown
- 1994-02-08 NO NO940421A patent/NO940421L/no unknown
- 1994-07-05 US US08/270,481 patent/US5536861A/en not_active Expired - Lifetime
-
1997
- 1997-08-13 GR GR970402082T patent/GR3024439T3/el unknown
-
1998
- 1998-06-04 HK HK98104874A patent/HK1005743A1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP3502140B2 (ja) | 2004-03-02 |
| DE69403358D1 (de) | 1997-07-03 |
| AU5491894A (en) | 1994-08-11 |
| CA2115121A1 (en) | 1994-08-10 |
| JPH06256421A (ja) | 1994-09-13 |
| MX9400946A (es) | 1994-08-31 |
| ES2102795T3 (es) | 1997-08-01 |
| IL108540A0 (en) | 1994-05-30 |
| EP0611782A1 (en) | 1994-08-24 |
| NO940421D0 (no) | 1994-02-08 |
| NO940421L (no) | 1994-08-10 |
| ATE153679T1 (de) | 1997-06-15 |
| TW243455B (cg-RX-API-DMAC10.html) | 1995-03-21 |
| FI940558A7 (fi) | 1994-08-10 |
| ZA94844B (en) | 1994-09-05 |
| IL108540A (en) | 1998-07-15 |
| GR3024439T3 (en) | 1997-11-28 |
| FI940558A0 (fi) | 1994-02-07 |
| DK0611782T3 (da) | 1997-07-14 |
| US5536861A (en) | 1996-07-16 |
| EP0611782B1 (en) | 1997-05-28 |
| HK1005743A1 (en) | 1999-01-22 |
| NZ250832A (en) | 1996-02-27 |
| US5358688A (en) | 1994-10-25 |
| AU676238B2 (en) | 1997-03-06 |
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