AU774151B2 - Zwitterionic siloxane polymers and ionically cross-linked polymers formed therefrom - Google Patents
Zwitterionic siloxane polymers and ionically cross-linked polymers formed therefrom Download PDFInfo
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- AU774151B2 AU774151B2 AU24714/01A AU2471401A AU774151B2 AU 774151 B2 AU774151 B2 AU 774151B2 AU 24714/01 A AU24714/01 A AU 24714/01A AU 2471401 A AU2471401 A AU 2471401A AU 774151 B2 AU774151 B2 AU 774151B2
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- 229920000642 polymer Polymers 0.000 title claims description 42
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims description 28
- 229920006037 cross link polymer Polymers 0.000 title description 3
- -1 polysiloxane Polymers 0.000 claims description 120
- 239000000203 mixture Substances 0.000 claims description 111
- 229920001296 polysiloxane Polymers 0.000 claims description 93
- 239000002253 acid Substances 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 32
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 32
- 229920002545 silicone oil Polymers 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 239000000376 reactant Substances 0.000 claims description 21
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 claims description 17
- 239000002537 cosmetic Substances 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 230000001166 anti-perspirative effect Effects 0.000 claims description 14
- 239000003213 antiperspirant Substances 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000000834 fixative Substances 0.000 claims description 10
- 210000004209 hair Anatomy 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 125000004427 diamine group Chemical group 0.000 claims description 8
- 230000000475 sunscreen effect Effects 0.000 claims description 8
- 239000000516 sunscreening agent Substances 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- KAYAKFYASWYOEB-UHFFFAOYSA-N 3-octadec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC=CC1CC(=O)OC1=O KAYAKFYASWYOEB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 5
- 239000002453 shampoo Substances 0.000 claims description 5
- 229910018557 Si O Inorganic materials 0.000 claims description 4
- 239000006210 lotion Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 239000002781 deodorant agent Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 3
- 229940014800 succinic anhydride Drugs 0.000 claims description 3
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 3
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 2
- 230000002500 effect on skin Effects 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- FLISWPFVWWWNNP-BQYQJAHWSA-N dihydro-3-(1-octenyl)-2,5-furandione Chemical compound CCCCCC\C=C\C1CC(=O)OC1=O FLISWPFVWWWNNP-BQYQJAHWSA-N 0.000 claims 1
- 239000012530 fluid Substances 0.000 description 43
- 239000000047 product Substances 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000003921 oil Substances 0.000 description 28
- 235000019198 oils Nutrition 0.000 description 27
- 239000000499 gel Substances 0.000 description 24
- 238000012360 testing method Methods 0.000 description 20
- 239000003513 alkali Substances 0.000 description 14
- 239000004615 ingredient Substances 0.000 description 14
- 239000012071 phase Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 238000009835 boiling Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- 150000003141 primary amines Chemical class 0.000 description 13
- 125000004122 cyclic group Chemical group 0.000 description 12
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 239000001993 wax Substances 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000004166 Lanolin Substances 0.000 description 7
- 150000004678 hydrides Chemical class 0.000 description 7
- 235000019388 lanolin Nutrition 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 229940039717 lanolin Drugs 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 229940086555 cyclomethicone Drugs 0.000 description 5
- 239000003205 fragrance Substances 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 238000004078 waterproofing Methods 0.000 description 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical group [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000003974 emollient agent Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 229920000554 ionomer Polymers 0.000 description 4
- OQILCOQZDHPEAZ-UHFFFAOYSA-N octyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCCCCCCC OQILCOQZDHPEAZ-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 3
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 102000011782 Keratins Human genes 0.000 description 3
- 108010076876 Keratins Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- WYANSMZYIOPJFV-UHFFFAOYSA-L aluminum;2-aminoacetic acid;zirconium(4+);chloride;hydroxide;hydrate Chemical compound O.[OH-].[Al+3].[Cl-].[Zr+4].NCC(O)=O WYANSMZYIOPJFV-UHFFFAOYSA-L 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229930014626 natural product Natural products 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IUMSDRXLFWAGNT-UHFFFAOYSA-N Dodecamethylcyclohexasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 IUMSDRXLFWAGNT-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- NWGKJDSIEKMTRX-BFWOXRRGSA-N [(2r)-2-[(3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)C1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-BFWOXRRGSA-N 0.000 description 2
- ZGUQGPFMMTZGBQ-UHFFFAOYSA-N [Al].[Al].[Zr] Chemical compound [Al].[Al].[Zr] ZGUQGPFMMTZGBQ-UHFFFAOYSA-N 0.000 description 2
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- IGODOXYLBBXFDW-UHFFFAOYSA-N alpha-Terpinyl acetate Chemical compound CC(=O)OC(C)(C)C1CCC(C)=CC1 IGODOXYLBBXFDW-UHFFFAOYSA-N 0.000 description 2
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 2
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- 125000000129 anionic group Chemical group 0.000 description 2
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- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 2
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- 238000001035 drying Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
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- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- NFVSFLUJRHRSJG-UHFFFAOYSA-N hexadecamethylheptasiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C NFVSFLUJRHRSJG-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
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Classifications
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
- A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0208—Tissues; Wipes; Patches
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/042—Gels
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5428—Polymers characterized by specific structures/properties characterized by the charge amphoteric or zwitterionic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/427216 | 1999-10-26 | ||
| US09/427,216 US6124490A (en) | 1999-10-26 | 1999-10-26 | Zwitterionic siloxane polymers and ionically cross-linked polymers formed therefrom |
| PCT/US2000/041558 WO2001030886A2 (en) | 1999-10-26 | 2000-10-26 | Zwitterionic siloxane polymers and ionically cross-linked polymers formed therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2471401A AU2471401A (en) | 2001-05-08 |
| AU774151B2 true AU774151B2 (en) | 2004-06-17 |
Family
ID=23693944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU24714/01A Ceased AU774151B2 (en) | 1999-10-26 | 2000-10-26 | Zwitterionic siloxane polymers and ionically cross-linked polymers formed therefrom |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6124490A (enExample) |
| EP (1) | EP1224239B1 (enExample) |
| JP (1) | JP2003513129A (enExample) |
| KR (1) | KR100656739B1 (enExample) |
| CN (1) | CN1206281C (enExample) |
| AR (1) | AR027874A1 (enExample) |
| AT (1) | ATE240989T1 (enExample) |
| AU (1) | AU774151B2 (enExample) |
| BR (1) | BR0015226B1 (enExample) |
| CA (1) | CA2387498C (enExample) |
| DE (1) | DE60002907T2 (enExample) |
| ES (1) | ES2199890T3 (enExample) |
| IL (2) | IL149196A0 (enExample) |
| MX (1) | MXPA02003918A (enExample) |
| NZ (1) | NZ518366A (enExample) |
| TR (1) | TR200201064T2 (enExample) |
| WO (1) | WO2001030886A2 (enExample) |
Families Citing this family (61)
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| CN1213716C (zh) * | 1999-08-30 | 2005-08-10 | 株式会社钟纺化妆品 | 化妆品 |
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| US6679979B2 (en) * | 2001-12-12 | 2004-01-20 | Ballard Power Systems Inc. | Aqueous ionomeric gels and products and methods related thereto |
| JP2003321544A (ja) * | 2002-04-30 | 2003-11-14 | Chisso Corp | 感熱応答性シラン化合物およびその製造方法ならびにこれを含む感熱応答性材料 |
| FR2840615B1 (fr) * | 2002-06-10 | 2005-08-05 | Oreal | Polymeres a base d'organosiloxanes et leur utilisation dans des compositions cosmetiques ou dermatologiques |
| DE10234262A1 (de) * | 2002-07-27 | 2004-02-19 | Beiersdorf Ag | Haarshampoo für feines und fettiges Haar |
| US8900607B1 (en) | 2002-09-25 | 2014-12-02 | Chemsil Silicones, Inc. | Clear, greaseless skin-care compositions |
| DE60334921D1 (de) | 2002-09-26 | 2010-12-23 | Oreal | Zusammensetzung mit einem blockpolymer und einem filmbildenden mittel |
| GB0300808D0 (en) * | 2003-01-14 | 2003-02-12 | Unilever Plc | Home and personal care compositions with lubricants |
| US6838541B2 (en) * | 2003-02-12 | 2005-01-04 | Dow Corning Corporation | Method of making siloxane-based polyamide elastomers |
| US20050037041A1 (en) * | 2003-02-28 | 2005-02-17 | David Schlossman | Duplex coated color lake and other powders, their preparation and cosmetic and other uses |
| GB0308062D0 (en) * | 2003-04-08 | 2003-05-14 | Unilever Plc | Cosmetic composition |
| GB0328693D0 (en) * | 2003-12-11 | 2004-01-14 | Ici Plc | Metal oxide dispersions |
| DE10358060A1 (de) * | 2003-12-11 | 2005-07-14 | Wacker-Chemie Gmbh | Verfahren zur Herstellung hochviskoser Organopolysiloxane |
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| FR2873033A1 (fr) | 2004-07-16 | 2006-01-20 | Oreal | Composition cosmetique compenant un polymere de silicone defini et un agent gelifiant. |
| CN1914291B (zh) * | 2004-09-02 | 2010-10-27 | 横滨橡胶株式会社 | 光纤用粘结剂组合物 |
| EP1676556B1 (en) | 2004-10-22 | 2012-01-11 | L'Oréal | Cosmetic composition containing a polyorganosiloxane polymer |
| DE602005011330D1 (de) * | 2004-12-15 | 2009-01-08 | Dow Corning | Sulfonatfunktionelle organopolysiloxane |
| KR100930874B1 (ko) * | 2005-06-10 | 2009-12-10 | (주)아모레퍼시픽 | 유기 또는 무기 입자의 표면이 발수성 극박막 층으로표면개질된 분체의 제조방법 |
| US9649513B2 (en) * | 2006-03-24 | 2017-05-16 | Colgate—Palmolive Company | Aerosol dispenser |
| US7601766B2 (en) * | 2006-06-30 | 2009-10-13 | Bausch & Lomb Incorporated | Carboxylic siloxanyl monomers with pendant polymerizable groups |
| MY153647A (en) * | 2007-05-01 | 2015-03-13 | Akzo Nobel Coatings Int Bv | Anti-fouling coating compositions containing a carboxyl-functional organosilicone |
| JP5416715B2 (ja) * | 2007-12-21 | 2014-02-12 | ダウ・コーニング・コーポレイション | イオノマー性シリコーン熱可塑性エラストマー |
| US20090258889A1 (en) | 2008-04-11 | 2009-10-15 | Whitmire Micro-Gen Research Laboratories, Inc. | Pesticidal compositions |
| JP5196193B2 (ja) * | 2009-08-27 | 2013-05-15 | 信越化学工業株式会社 | オルガノポリシロキサン化合物を含有する化粧料 |
| US20110052523A1 (en) * | 2009-08-27 | 2011-03-03 | Hiroyuki Moriya | Organopolysiloxane compound and amidoamine compound, and cosmetic preparation |
| BR112012024963A2 (pt) * | 2010-04-01 | 2016-07-12 | Procter & Gamble | organossilicones |
| JP5671989B2 (ja) * | 2010-12-13 | 2015-02-18 | 信越化学工業株式会社 | 毛髪化粧料 |
| GB201102750D0 (en) | 2011-02-16 | 2011-03-30 | Dow Corning | Foam control composition |
| US8653190B2 (en) * | 2011-08-08 | 2014-02-18 | 3M Innovative Properties Company | Curable cyclic anhydride copolymer/silicone composition |
| IN2014MN01346A (enExample) * | 2012-01-04 | 2015-06-12 | Momentive Performance Mat Inc | |
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| US9895307B2 (en) | 2012-01-04 | 2018-02-20 | Momentive Performance Materials Inc. | Personal care compositions containing ionic silicone and film-forming agent |
| RU2615144C2 (ru) | 2012-02-16 | 2017-04-04 | Дау Корнинг Корпорейшн | Гранулированное вещество для контроля пенообразования для цикла полоскания с использованием силоксанового воска |
| WO2014113643A1 (en) * | 2013-01-18 | 2014-07-24 | Georgetown University | Amino-substituted polysiloxanes combined with polymerizable and unpolymerizable organic acids |
| GB201314284D0 (en) | 2013-08-09 | 2013-09-25 | Dow Corning | Cosmetic compositions containing silicones |
| WO2015022165A1 (en) | 2013-08-13 | 2015-02-19 | Dow Corning Corporation | Method of forming an antifoam granule |
| JP6585066B2 (ja) | 2013-10-31 | 2019-10-02 | ダウ シリコーンズ コーポレーション | 架橋組成物及びその生成方法 |
| KR102313564B1 (ko) | 2013-10-31 | 2021-10-19 | 다우 실리콘즈 코포레이션 | 카르복시 작용성 엘라스토머를 포함하는 화장용 조성물 |
| KR102324877B1 (ko) | 2013-10-31 | 2021-11-09 | 다우 실리콘즈 코포레이션 | 가교결합된 조성물 및 이의 형성 방법 |
| CN106456507B (zh) * | 2014-05-21 | 2019-05-10 | 美国陶氏有机硅公司 | 交联氨基硅氧烷聚合物的乳液 |
| EP3145982B8 (en) * | 2014-05-21 | 2018-09-05 | Dow Silicones Corporation | Cross-linked aminosiloxane polymer and method of forming |
| US9498409B2 (en) | 2014-12-16 | 2016-11-22 | Momentive Performance Materials Inc. | Cosmetic skin covering sheets and their method of preparation |
| US20160166494A1 (en) * | 2014-12-16 | 2016-06-16 | Momentive Performance Materials Inc. | Cosmetic composition and method of preparation |
| US9744119B2 (en) | 2014-12-16 | 2017-08-29 | Momentive Performance Materials Inc. | Cosmetic composition and method of preparation |
| FR3030536B1 (fr) * | 2014-12-22 | 2018-06-15 | Institut National Des Sciences Appliquees Lyon | Organopolysiloxanes et leur procede de preparation |
| WO2016164292A1 (en) * | 2015-04-08 | 2016-10-13 | Dow Corning Corporation | Fluid compositions and personal care |
| KR102134530B1 (ko) | 2016-03-14 | 2020-07-15 | 다우 실리콘즈 코포레이션 | 조성물 및 제조 방법 |
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| FR3052784A1 (fr) * | 2016-06-21 | 2017-12-22 | Bluestar Silicones France | Procede de lutte contre l'apparition de brouillard dans un dispositif a cylindres lors de l'enduction de supports flexibles avec une composition silicone liquide reticulable |
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| FR3078335B1 (fr) | 2018-02-28 | 2020-12-25 | Elkem Silicones France Sas | Materiaux silicones |
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| CN110372284A (zh) * | 2019-06-12 | 2019-10-25 | 毛军华 | 一种瓷砖粘胶泥 |
| CN112062965B (zh) * | 2020-08-11 | 2022-10-04 | 浙江恒业成有机硅有限公司 | 一种长链烷基及两性离子共改性抗菌型硅油乳液及其制备方法 |
| CN112142785A (zh) * | 2020-09-09 | 2020-12-29 | 深圳市旭生三益科技有限公司 | 膦酸铵两性离子硅烷偶联剂及硅氧烷环体及其制备方法 |
| CN114181531B (zh) * | 2021-12-01 | 2022-12-27 | 武汉工程大学 | 用于制备致动器件的离子聚合物、致动器件及其制备方法 |
| US11891513B2 (en) * | 2022-02-07 | 2024-02-06 | Formlabs Inc. | Thiol-ene silicone additive fabrication |
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| EP0377458A1 (en) * | 1989-01-05 | 1990-07-11 | Dow Corning Corporation | Water sheeting zwitterionomeric aminofunctional siloxanes |
| US5194251A (en) * | 1992-02-10 | 1993-03-16 | Dow Corning Corporation | Hair treatment with zwitterionomeric siloxanes |
| US5596061A (en) * | 1993-12-28 | 1997-01-21 | Mona Industries, Inc. | Organosilicone having a carboxyl functional group thereon |
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1999
- 1999-10-26 US US09/427,216 patent/US6124490A/en not_active Expired - Lifetime
-
2000
- 2000-10-26 NZ NZ518366A patent/NZ518366A/en unknown
- 2000-10-26 MX MXPA02003918A patent/MXPA02003918A/es active IP Right Grant
- 2000-10-26 KR KR1020027005015A patent/KR100656739B1/ko not_active Expired - Fee Related
- 2000-10-26 AR ARP000105629A patent/AR027874A1/es active IP Right Grant
- 2000-10-26 JP JP2001533881A patent/JP2003513129A/ja active Pending
- 2000-10-26 IL IL14919600A patent/IL149196A0/xx active IP Right Grant
- 2000-10-26 ES ES00988510T patent/ES2199890T3/es not_active Expired - Lifetime
- 2000-10-26 TR TR2002/01064T patent/TR200201064T2/xx unknown
- 2000-10-26 EP EP00988510A patent/EP1224239B1/en not_active Expired - Lifetime
- 2000-10-26 AU AU24714/01A patent/AU774151B2/en not_active Ceased
- 2000-10-26 BR BRPI0015226-9A patent/BR0015226B1/pt not_active IP Right Cessation
- 2000-10-26 CA CA2387498A patent/CA2387498C/en not_active Expired - Fee Related
- 2000-10-26 WO PCT/US2000/041558 patent/WO2001030886A2/en not_active Ceased
- 2000-10-26 DE DE60002907T patent/DE60002907T2/de not_active Expired - Lifetime
- 2000-10-26 AT AT00988510T patent/ATE240989T1/de not_active IP Right Cessation
- 2000-10-26 CN CNB00814530XA patent/CN1206281C/zh not_active Expired - Fee Related
-
2002
- 2002-04-16 IL IL149196A patent/IL149196A/en not_active IP Right Cessation
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0377458A1 (en) * | 1989-01-05 | 1990-07-11 | Dow Corning Corporation | Water sheeting zwitterionomeric aminofunctional siloxanes |
| US5194251A (en) * | 1992-02-10 | 1993-03-16 | Dow Corning Corporation | Hair treatment with zwitterionomeric siloxanes |
| US5596061A (en) * | 1993-12-28 | 1997-01-21 | Mona Industries, Inc. | Organosilicone having a carboxyl functional group thereon |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE240989T1 (de) | 2003-06-15 |
| IL149196A0 (en) | 2002-11-10 |
| DE60002907D1 (de) | 2003-06-26 |
| CA2387498C (en) | 2010-06-29 |
| EP1224239A2 (en) | 2002-07-24 |
| TR200201064T2 (tr) | 2002-09-23 |
| AR027874A1 (es) | 2003-04-16 |
| BR0015226B1 (pt) | 2011-05-17 |
| DE60002907T2 (de) | 2004-03-11 |
| ES2199890T3 (es) | 2004-03-01 |
| CN1384857A (zh) | 2002-12-11 |
| NZ518366A (en) | 2004-01-30 |
| IL149196A (en) | 2007-07-24 |
| US6124490A (en) | 2000-09-26 |
| EP1224239B1 (en) | 2003-05-21 |
| MXPA02003918A (es) | 2004-12-06 |
| AU2471401A (en) | 2001-05-08 |
| WO2001030886A3 (en) | 2001-09-13 |
| CA2387498A1 (en) | 2001-05-03 |
| KR100656739B1 (ko) | 2006-12-13 |
| KR20020070972A (ko) | 2002-09-11 |
| JP2003513129A (ja) | 2003-04-08 |
| CN1206281C (zh) | 2005-06-15 |
| BR0015226A (pt) | 2002-07-16 |
| WO2001030886A2 (en) | 2001-05-03 |
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