CA2461553A1 - Water-in-oil emulsions comprising vinyl polymers carrying acidic groups in side chains, compositions, and methods - Google Patents
Water-in-oil emulsions comprising vinyl polymers carrying acidic groups in side chains, compositions, and methods Download PDFInfo
- Publication number
- CA2461553A1 CA2461553A1 CA002461553A CA2461553A CA2461553A1 CA 2461553 A1 CA2461553 A1 CA 2461553A1 CA 002461553 A CA002461553 A CA 002461553A CA 2461553 A CA2461553 A CA 2461553A CA 2461553 A1 CA2461553 A1 CA 2461553A1
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- CA
- Canada
- Prior art keywords
- water
- containing side
- group
- side chains
- oil emulsion
- 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.)
- Abandoned
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- 239000000203 mixture Substances 0.000 title claims abstract description 132
- 239000000839 emulsion Substances 0.000 title claims abstract description 124
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 56
- 238000000034 method Methods 0.000 title claims abstract description 31
- 230000002378 acidificating effect Effects 0.000 title description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
- 125000000129 anionic group Chemical group 0.000 claims abstract description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 20
- 239000000178 monomer Substances 0.000 claims description 114
- 239000003921 oil Substances 0.000 claims description 112
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 81
- 239000007762 w/o emulsion Substances 0.000 claims description 70
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 34
- 229920000642 polymer Polymers 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 32
- -1 conditioners Substances 0.000 claims description 30
- 230000003020 moisturizing effect Effects 0.000 claims description 25
- 239000000047 product Substances 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- 229910052708 sodium Inorganic materials 0.000 claims description 20
- 229910052791 calcium Inorganic materials 0.000 claims description 19
- 229910052744 lithium Inorganic materials 0.000 claims description 19
- 229910052749 magnesium Inorganic materials 0.000 claims description 19
- 229910052700 potassium Inorganic materials 0.000 claims description 19
- 229910052725 zinc Inorganic materials 0.000 claims description 19
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- 150000003512 tertiary amines Chemical class 0.000 claims description 18
- 230000002421 anti-septic effect Effects 0.000 claims description 17
- 239000004599 antimicrobial Substances 0.000 claims description 17
- 150000003141 primary amines Chemical class 0.000 claims description 17
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 239000008177 pharmaceutical agent Substances 0.000 claims description 11
- 230000000845 anti-microbial effect Effects 0.000 claims description 10
- 230000000249 desinfective effect Effects 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 8
- 239000003906 humectant Substances 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
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- 238000012377 drug delivery Methods 0.000 claims description 5
- 239000000077 insect repellent Substances 0.000 claims description 5
- 239000002562 thickening agent Substances 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- 230000001166 anti-perspirative effect Effects 0.000 claims description 4
- 239000003213 antiperspirant Substances 0.000 claims description 4
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- 239000012676 herbal extract Substances 0.000 claims description 4
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- 239000004094 surface-active agent Substances 0.000 claims description 4
- CPKVUHPKYQGHMW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;molecular iodine Chemical group II.C=CN1CCCC1=O CPKVUHPKYQGHMW-UHFFFAOYSA-N 0.000 claims description 3
- 229920000153 Povidone-iodine Polymers 0.000 claims description 3
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- 239000003212 astringent agent Substances 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
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- 229960001621 povidone-iodine Drugs 0.000 claims description 3
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
- 239000000058 anti acne agent Substances 0.000 claims description 2
- 229940124340 antiacne agent Drugs 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims description 2
- 235000005822 corn Nutrition 0.000 claims description 2
- 239000000796 flavoring agent Substances 0.000 claims description 2
- 235000013355 food flavoring agent Nutrition 0.000 claims description 2
- 239000003051 hair bleaching agent Substances 0.000 claims description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 239000003380 propellant Substances 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 239000002453 shampoo Substances 0.000 claims description 2
- 201000010153 skin papilloma Diseases 0.000 claims description 2
- 230000000475 sunscreen effect Effects 0.000 claims description 2
- 238000001356 surgical procedure Methods 0.000 claims description 2
- 239000011782 vitamin Substances 0.000 claims description 2
- 229940088594 vitamin Drugs 0.000 claims description 2
- 229930003231 vitamin Natural products 0.000 claims description 2
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- 125000003277 amino group Chemical group 0.000 claims 12
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 12
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- 206010040829 Skin discolouration Diseases 0.000 claims 1
- 239000007854 depigmenting agent Substances 0.000 claims 1
- 239000000118 hair dye Substances 0.000 claims 1
- 239000000454 talc Substances 0.000 claims 1
- 229910052623 talc Inorganic materials 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 64
- 239000003995 emulsifying agent Substances 0.000 description 25
- 210000001519 tissue Anatomy 0.000 description 25
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 24
- 239000000463 material Substances 0.000 description 19
- 239000000853 adhesive Substances 0.000 description 18
- 230000001070 adhesive effect Effects 0.000 description 18
- 229920001577 copolymer Polymers 0.000 description 18
- 239000003974 emollient agent Substances 0.000 description 18
- 229920001223 polyethylene glycol Polymers 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000009472 formulation Methods 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- 239000002537 cosmetic Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 12
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 11
- 229920001451 polypropylene glycol Polymers 0.000 description 11
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 11
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 11
- 239000002202 Polyethylene glycol Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000003999 initiator Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 229920000058 polyacrylate Polymers 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000012847 fine chemical Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- IRLPACMLTUPBCL-KQYNXXCUSA-N 5'-adenylyl sulfate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O IRLPACMLTUPBCL-KQYNXXCUSA-N 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 150000001412 amines Chemical group 0.000 description 6
- 239000012986 chain transfer agent Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 238000012546 transfer Methods 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
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 5
- 206010013786 Dry skin Diseases 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- 206010052428 Wound Diseases 0.000 description 5
- 208000027418 Wounds and injury Diseases 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 210000001124 body fluid Anatomy 0.000 description 5
- 239000010839 body fluid Substances 0.000 description 5
- 239000007810 chemical reaction solvent Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 description 5
- 230000037336 dry skin Effects 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 210000004400 mucous membrane Anatomy 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 5
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 4
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 4
- 102100026735 Coagulation factor VIII Human genes 0.000 description 4
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 4
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
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- 229910052757 nitrogen Inorganic materials 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
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- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 3
- BRORPGSJXSLXKN-UHFFFAOYSA-N 6-methylheptyl 3,5,5-trimethylhexanoate Chemical compound CC(C)CCCCCOC(=O)CC(C)CC(C)(C)C BRORPGSJXSLXKN-UHFFFAOYSA-N 0.000 description 3
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- 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 3
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- CKQNDABUGIXFCL-UHFFFAOYSA-N 2-(2-octanoyloxyethoxy)ethyl octanoate Chemical compound CCCCCCCC(=O)OCCOCCOC(=O)CCCCCCC CKQNDABUGIXFCL-UHFFFAOYSA-N 0.000 description 2
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- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 2
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- HBTAOSGHCXUEKI-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HBTAOSGHCXUEKI-UHFFFAOYSA-N 0.000 description 2
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- 229920002633 Kraton (polymer) Polymers 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
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Landscapes
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Medicinal Preparation (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/967,578 US6951642B2 (en) | 2001-09-28 | 2001-09-28 | Water-in-oil emulsions with anionic groups, compositions, and methods |
| US09/967,578 | 2001-09-28 | ||
| PCT/US2002/022991 WO2003028766A1 (en) | 2001-09-28 | 2002-07-19 | Water-in-oil emulsions comprising vinyl polymers carrying acidic groups in side chains, compositions, and methods |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2461553A1 true CA2461553A1 (en) | 2003-04-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002461553A Abandoned CA2461553A1 (en) | 2001-09-28 | 2002-07-19 | Water-in-oil emulsions comprising vinyl polymers carrying acidic groups in side chains, compositions, and methods |
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| EP (1) | EP1432449B1 (enExample) |
| JP (2) | JP2005517518A (enExample) |
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| AU (1) | AU2002320641B9 (enExample) |
| BR (1) | BR0212877A (enExample) |
| CA (1) | CA2461553A1 (enExample) |
| DE (1) | DE60225931T2 (enExample) |
| MX (1) | MXPA04002781A (enExample) |
| NO (1) | NO20041735L (enExample) |
| WO (1) | WO2003028766A1 (enExample) |
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-
2001
- 2001-09-28 US US09/967,578 patent/US6951642B2/en not_active Expired - Lifetime
-
2002
- 2002-07-19 MX MXPA04002781A patent/MXPA04002781A/es active IP Right Grant
- 2002-07-19 CA CA002461553A patent/CA2461553A1/en not_active Abandoned
- 2002-07-19 BR BR0212877-2A patent/BR0212877A/pt not_active Application Discontinuation
- 2002-07-19 DE DE60225931T patent/DE60225931T2/de not_active Expired - Lifetime
- 2002-07-19 AU AU2002320641A patent/AU2002320641B9/en not_active Ceased
- 2002-07-19 WO PCT/US2002/022991 patent/WO2003028766A1/en not_active Ceased
- 2002-07-19 AT AT02750174T patent/ATE390936T1/de not_active IP Right Cessation
- 2002-07-19 EP EP02750174A patent/EP1432449B1/en not_active Expired - Lifetime
- 2002-07-19 JP JP2003532095A patent/JP2005517518A/ja active Pending
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2004
- 2004-04-28 NO NO20041735A patent/NO20041735L/no not_active Application Discontinuation
-
2005
- 2005-10-03 US US11/242,314 patent/US8636993B2/en active Active
-
2010
- 2010-06-23 JP JP2010143073A patent/JP2010235625A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| NO20041735L (no) | 2004-06-28 |
| JP2010235625A (ja) | 2010-10-21 |
| AU2002320641B9 (en) | 2008-06-19 |
| EP1432449A1 (en) | 2004-06-30 |
| DE60225931D1 (de) | 2008-05-15 |
| EP1432449B1 (en) | 2008-04-02 |
| US20060029569A1 (en) | 2006-02-09 |
| US6951642B2 (en) | 2005-10-04 |
| MXPA04002781A (es) | 2004-07-29 |
| ATE390936T1 (de) | 2008-04-15 |
| WO2003028766A1 (en) | 2003-04-10 |
| US8636993B2 (en) | 2014-01-28 |
| US20030118629A1 (en) | 2003-06-26 |
| JP2005517518A (ja) | 2005-06-16 |
| BR0212877A (pt) | 2004-10-13 |
| AU2002320641B2 (en) | 2008-04-24 |
| DE60225931T2 (de) | 2009-04-09 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |