MXPA04006839A - Composiciones y metodos de formacion de pelicula. - Google Patents
Composiciones y metodos de formacion de pelicula.Info
- Publication number
- MXPA04006839A MXPA04006839A MXPA04006839A MXPA04006839A MXPA04006839A MX PA04006839 A MXPA04006839 A MX PA04006839A MX PA04006839 A MXPA04006839 A MX PA04006839A MX PA04006839 A MXPA04006839 A MX PA04006839A MX PA04006839 A MXPA04006839 A MX PA04006839A
- Authority
- MX
- Mexico
- Prior art keywords
- polymer
- weight
- water
- composition
- amine
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 447
- 238000000034 method Methods 0.000 title claims abstract description 51
- 229920000642 polymer Polymers 0.000 claims abstract description 304
- 239000000178 monomer Substances 0.000 claims abstract description 166
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 101
- 239000004094 surface-active agent Substances 0.000 claims abstract description 99
- 125000003277 amino group Chemical group 0.000 claims abstract description 96
- 150000001412 amines Chemical class 0.000 claims abstract description 88
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 49
- 239000013543 active substance Substances 0.000 claims abstract description 47
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 26
- 239000000243 solution Substances 0.000 claims description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 64
- CPKVUHPKYQGHMW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;molecular iodine Chemical group II.C=CN1CCCC1=O CPKVUHPKYQGHMW-UHFFFAOYSA-N 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 230000000845 anti-microbial effect Effects 0.000 claims description 44
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 40
- -1 alkyl phosphates Chemical class 0.000 claims description 39
- 210000001519 tissue Anatomy 0.000 claims description 35
- 229920000153 Povidone-iodine Polymers 0.000 claims description 29
- 229960001621 povidone-iodine Drugs 0.000 claims description 29
- 239000004599 antimicrobial Substances 0.000 claims description 28
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 25
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 24
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 24
- 239000011630 iodine Substances 0.000 claims description 24
- 229910052740 iodine Inorganic materials 0.000 claims description 24
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 19
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 18
- 229910019142 PO4 Inorganic materials 0.000 claims description 17
- 235000021317 phosphate Nutrition 0.000 claims description 16
- 230000009467 reduction Effects 0.000 claims description 16
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 15
- 239000003945 anionic surfactant Substances 0.000 claims description 15
- 239000007853 buffer solution Substances 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 12
- 239000002736 nonionic surfactant Substances 0.000 claims description 11
- 230000003260 anti-sepsis Effects 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- 239000004744 fabric Substances 0.000 claims description 8
- 210000004400 mucous membrane Anatomy 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 6
- 239000002537 cosmetic Substances 0.000 claims description 6
- 238000009826 distribution Methods 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002280 amphoteric surfactant Substances 0.000 claims description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- 230000000699 topical effect Effects 0.000 claims description 4
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 claims description 3
- 241000191963 Staphylococcus epidermidis Species 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 229940127557 pharmaceutical product Drugs 0.000 claims description 3
- NUKPPZSTCYEEIZ-UHFFFAOYSA-N N,N-dimethylhydroxylamine 2-methylprop-2-enoic acid Chemical compound CN(C)O.CC(=C)C(O)=O NUKPPZSTCYEEIZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000000249 desinfective effect Effects 0.000 claims description 2
- 125000001302 tertiary amino group Chemical class 0.000 claims 1
- 239000010408 film Substances 0.000 description 63
- 238000002360 preparation method Methods 0.000 description 60
- 238000012360 testing method Methods 0.000 description 58
- 239000000047 product Substances 0.000 description 33
- 229940064804 betadine Drugs 0.000 description 30
- 150000003512 tertiary amines Chemical class 0.000 description 26
- 238000009472 formulation Methods 0.000 description 25
- 239000007787 solid Substances 0.000 description 25
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 24
- 229960002358 iodine Drugs 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 230000002421 anti-septic effect Effects 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 18
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- 239000000872 buffer Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 125000000524 functional group Chemical group 0.000 description 16
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 16
- 238000005201 scrubbing Methods 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 238000007792 addition Methods 0.000 description 15
- 238000005070 sampling Methods 0.000 description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical class OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 13
- 238000001035 drying Methods 0.000 description 13
- 239000006185 dispersion Substances 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 230000000813 microbial effect Effects 0.000 description 12
- 239000000523 sample Substances 0.000 description 12
- 229960003500 triclosan Drugs 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- YZIYKJHYYHPJIB-UUPCJSQJSA-N chlorhexidine gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 YZIYKJHYYHPJIB-UUPCJSQJSA-N 0.000 description 10
- 229960003333 chlorhexidine gluconate Drugs 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 10
- 229940035535 iodophors Drugs 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 8
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical class CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 235000015165 citric acid Nutrition 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 210000000245 forearm Anatomy 0.000 description 8
- 239000004310 lactic acid Substances 0.000 description 8
- 235000014655 lactic acid Nutrition 0.000 description 8
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- 239000007800 oxidant agent Substances 0.000 description 8
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- 229920000058 polyacrylate Polymers 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 241000283973 Oryctolagus cuniculus Species 0.000 description 7
- 206010052428 Wound Diseases 0.000 description 7
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- 229940064004 antiseptic throat preparations Drugs 0.000 description 7
- 230000005540 biological transmission Effects 0.000 description 7
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 7
- 238000005755 formation reaction Methods 0.000 description 7
- 150000001261 hydroxy acids Chemical class 0.000 description 7
- 239000000902 placebo Substances 0.000 description 7
- 238000010998 test method Methods 0.000 description 7
- JKXYOQDLERSFPT-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-octadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO JKXYOQDLERSFPT-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
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- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 210000003811 finger Anatomy 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 229940068196 placebo Drugs 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 5
- SSONCJTVDRSLNK-UHFFFAOYSA-N 2-methylprop-2-enoic acid;hydrochloride Chemical compound Cl.CC(=C)C(O)=O SSONCJTVDRSLNK-UHFFFAOYSA-N 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
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- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical group 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
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- 150000003871 sulfonates Chemical class 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 5
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- IAXXETNIOYFMLW-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) 2-methylprop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C(=C)C)CC1C2(C)C IAXXETNIOYFMLW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 241001465754 Metazoa Species 0.000 description 4
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- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
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- 238000005342 ion exchange Methods 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 230000008775 paternal effect Effects 0.000 description 4
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
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- 230000002035 prolonged effect Effects 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
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- GQWWGRUJOCIUKI-UHFFFAOYSA-N 2-[3-(2-methyl-1-oxopyrrolo[1,2-a]pyrazin-3-yl)propyl]guanidine Chemical group O=C1N(C)C(CCCN=C(N)N)=CN2C=CC=C21 GQWWGRUJOCIUKI-UHFFFAOYSA-N 0.000 description 3
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- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 3
- 206010013786 Dry skin Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 3
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- 229910052739 hydrogen Inorganic materials 0.000 description 3
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- 238000005259 measurement Methods 0.000 description 3
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- 125000005528 methosulfate group Chemical class 0.000 description 3
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
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- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
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- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 2
- 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 2
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 2
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- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
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- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
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- A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
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-
2002
- 2002-01-16 US US10/052,158 patent/US6838078B2/en not_active Expired - Lifetime
- 2002-12-05 BR BR0215518-4A patent/BR0215518A/pt not_active Application Discontinuation
- 2002-12-05 EP EP07113625A patent/EP1849487A3/en not_active Withdrawn
- 2002-12-05 DE DE60221900T patent/DE60221900T2/de not_active Expired - Lifetime
- 2002-12-05 ES ES02792331T patent/ES2290351T3/es not_active Expired - Lifetime
- 2002-12-05 WO PCT/US2002/038951 patent/WO2003061721A1/en not_active Ceased
- 2002-12-05 EP EP02792331A patent/EP1465676B1/en not_active Expired - Lifetime
- 2002-12-05 AT AT02792331T patent/ATE369881T1/de not_active IP Right Cessation
- 2002-12-05 KR KR10-2004-7010932A patent/KR20040075080A/ko not_active Abandoned
- 2002-12-05 CA CA002473841A patent/CA2473841A1/en not_active Abandoned
- 2002-12-05 JP JP2003561661A patent/JP4995406B2/ja not_active Expired - Fee Related
- 2002-12-05 AU AU2002357790A patent/AU2002357790B2/en not_active Ceased
- 2002-12-05 MX MXPA04006839A patent/MXPA04006839A/es active IP Right Grant
-
2004
- 2004-08-06 NO NO20043297A patent/NO20043297L/no not_active Application Discontinuation
- 2004-08-19 US US10/922,262 patent/US7323163B2/en not_active Expired - Lifetime
-
2010
- 2010-07-02 JP JP2010151930A patent/JP2010227617A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ATE369881T1 (de) | 2007-09-15 |
| JP2005520812A (ja) | 2005-07-14 |
| NO20043297L (no) | 2004-10-07 |
| KR20040075080A (ko) | 2004-08-26 |
| JP4995406B2 (ja) | 2012-08-08 |
| EP1849487A3 (en) | 2012-09-05 |
| JP2010227617A (ja) | 2010-10-14 |
| US6838078B2 (en) | 2005-01-04 |
| US20030194415A1 (en) | 2003-10-16 |
| DE60221900T2 (de) | 2008-05-08 |
| US20050025794A1 (en) | 2005-02-03 |
| CA2473841A1 (en) | 2003-07-31 |
| EP1465676B1 (en) | 2007-08-15 |
| EP1849487A2 (en) | 2007-10-31 |
| DE60221900D1 (de) | 2007-09-27 |
| ES2290351T3 (es) | 2008-02-16 |
| AU2002357790B2 (en) | 2008-03-06 |
| EP1465676A1 (en) | 2004-10-13 |
| BR0215518A (pt) | 2004-12-21 |
| WO2003061721A1 (en) | 2003-07-31 |
| US7323163B2 (en) | 2008-01-29 |
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