ZA200403168B - Water-in-oil emulsions comprising vinyl polymers carrying ethylene oxide groups in side chains, compositions and methods. - Google Patents
Water-in-oil emulsions comprising vinyl polymers carrying ethylene oxide groups in side chains, compositions and methods. Download PDFInfo
- Publication number
- ZA200403168B ZA200403168B ZA200403168A ZA200403168A ZA200403168B ZA 200403168 B ZA200403168 B ZA 200403168B ZA 200403168 A ZA200403168 A ZA 200403168A ZA 200403168 A ZA200403168 A ZA 200403168A ZA 200403168 B ZA200403168 B ZA 200403168B
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- ZA
- South Africa
- Prior art keywords
- water
- oil emulsion
- emulsion
- oil
- alkyl
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 124
- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000000839 emulsion Substances 0.000 title claims description 208
- 229920002554 vinyl polymer Polymers 0.000 title claims description 47
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 title claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 86
- 239000007762 w/o emulsion Substances 0.000 claims abstract description 77
- 229920000642 polymer Polymers 0.000 claims abstract description 57
- 239000004599 antimicrobial Substances 0.000 claims abstract description 22
- 230000001804 emulsifying effect Effects 0.000 claims abstract description 8
- 239000003921 oil Substances 0.000 claims description 142
- 239000000178 monomer Substances 0.000 claims description 89
- -1 conditioners Substances 0.000 claims description 55
- 238000002360 preparation method Methods 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 210000001519 tissue Anatomy 0.000 claims description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 239000000047 product Substances 0.000 claims description 25
- 239000006071 cream Substances 0.000 claims description 24
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 24
- 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 claims description 22
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 21
- 229960003333 chlorhexidine gluconate Drugs 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 15
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 15
- 230000003020 moisturizing effect Effects 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- 230000002421 anti-septic effect Effects 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 10
- 239000006210 lotion Substances 0.000 claims description 10
- 230000009467 reduction Effects 0.000 claims description 10
- 230000000845 anti-microbial effect Effects 0.000 claims description 9
- 210000004400 mucous membrane Anatomy 0.000 claims description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- CPKVUHPKYQGHMW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;molecular iodine Chemical group II.C=CN1CCCC1=O CPKVUHPKYQGHMW-UHFFFAOYSA-N 0.000 claims description 7
- 229920000153 Povidone-iodine Polymers 0.000 claims description 7
- 239000003906 humectant Substances 0.000 claims description 7
- 229920000728 polyester Polymers 0.000 claims description 7
- 229960001621 povidone-iodine Drugs 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000012867 bioactive agent Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000516 sunscreening agent Substances 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 239000002562 thickening agent Substances 0.000 claims description 6
- 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 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 230000000249 desinfective effect Effects 0.000 claims description 5
- 235000011187 glycerol Nutrition 0.000 claims description 5
- 239000000077 insect repellent Substances 0.000 claims description 5
- 239000008177 pharmaceutical agent Substances 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 239000003213 antiperspirant Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 239000002781 deodorant agent Substances 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 239000012676 herbal extract Substances 0.000 claims description 4
- 229940035535 iodophors Drugs 0.000 claims description 4
- 239000002304 perfume Substances 0.000 claims description 4
- 239000003755 preservative agent Substances 0.000 claims description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 4
- 238000013271 transdermal drug delivery Methods 0.000 claims description 4
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 claims description 3
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 claims description 3
- 230000001166 anti-perspirative effect Effects 0.000 claims description 3
- 239000003212 astringent agent Substances 0.000 claims description 3
- 229960003260 chlorhexidine Drugs 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 claims description 3
- 239000000499 gel Substances 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 238000012643 polycondensation polymerization Methods 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000000375 suspending agent Substances 0.000 claims description 3
- 229960003500 triclosan Drugs 0.000 claims description 3
- 239000001993 wax Substances 0.000 claims description 3
- VAZJLPXFVQHDFB-UHFFFAOYSA-N 1-(diaminomethylidene)-2-hexylguanidine Polymers CCCCCCN=C(N)N=C(N)N VAZJLPXFVQHDFB-UHFFFAOYSA-N 0.000 claims description 2
- 206010020649 Hyperkeratosis Diseases 0.000 claims description 2
- 229920002413 Polyhexanide Polymers 0.000 claims description 2
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 2
- 208000000260 Warts Diseases 0.000 claims description 2
- 240000008042 Zea mays Species 0.000 claims description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
- 150000001412 amines Chemical group 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
- 239000000872 buffer Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 235000005822 corn Nutrition 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 150000004665 fatty acids Chemical class 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
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 claims description 2
- 229960004068 hexachlorophene Drugs 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 239000003380 propellant Substances 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 239000002453 shampoo Substances 0.000 claims description 2
- 150000004756 silanes Chemical group 0.000 claims description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 2
- 229910001923 silver oxide Inorganic materials 0.000 claims description 2
- 229960003600 silver sulfadiazine Drugs 0.000 claims description 2
- UEJSSZHHYBHCEL-UHFFFAOYSA-N silver(1+) sulfadiazinate Chemical compound [Ag+].C1=CC(N)=CC=C1S(=O)(=O)[N-]C1=NC=CC=N1 UEJSSZHHYBHCEL-UHFFFAOYSA-N 0.000 claims description 2
- 201000010153 skin papilloma Diseases 0.000 claims description 2
- 230000000475 sunscreen effect Effects 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 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
- 235000013343 vitamin Nutrition 0.000 claims description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- 241000766026 Coregonus nasus Species 0.000 claims 1
- 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 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical group [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- 206010040829 Skin discolouration Diseases 0.000 claims 1
- 239000007854 depigmenting agent Substances 0.000 claims 1
- 229940050410 gluconate Drugs 0.000 claims 1
- 239000000118 hair dye Substances 0.000 claims 1
- 125000005395 methacrylic acid group Chemical group 0.000 claims 1
- 239000004332 silver Chemical group 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 150000003378 silver Chemical group 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 96
- 229920000058 polyacrylate Polymers 0.000 description 48
- 238000012360 testing method Methods 0.000 description 38
- 239000004615 ingredient Substances 0.000 description 28
- 238000009472 formulation Methods 0.000 description 27
- 229920001223 polyethylene glycol Polymers 0.000 description 25
- 239000000243 solution Substances 0.000 description 22
- 239000002537 cosmetic Substances 0.000 description 19
- 239000000853 adhesive Substances 0.000 description 18
- 230000001070 adhesive effect Effects 0.000 description 18
- 239000000463 material Substances 0.000 description 17
- 239000000523 sample Substances 0.000 description 17
- 239000002202 Polyethylene glycol Substances 0.000 description 16
- 230000004888 barrier function Effects 0.000 description 15
- 239000003974 emollient agent Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000003999 initiator Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000003995 emulsifying agent Substances 0.000 description 10
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000012546 transfer Methods 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 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 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000000645 desinfectant Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000007764 o/w emulsion Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000013112 stability test Methods 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 description 6
- DUDCYUDPBRJVLG-UHFFFAOYSA-N ethoxyethane methyl 2-methylprop-2-enoate Chemical compound CCOCC.COC(=O)C(C)=C DUDCYUDPBRJVLG-UHFFFAOYSA-N 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 229920001427 mPEG Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000010998 test method Methods 0.000 description 6
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 5
- 206010052428 Wound Diseases 0.000 description 5
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- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
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- 238000000926 separation method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 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 4
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 4
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
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- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 4
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- 238000005259 measurement Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 3
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- HCQHIEGYGGJLJU-UHFFFAOYSA-N didecyl hexanedioate Chemical compound CCCCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCCCC HCQHIEGYGGJLJU-UHFFFAOYSA-N 0.000 description 3
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- NNYBQONXHNTVIJ-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=C1C(C=CC=C1CC)=C1N2 NNYBQONXHNTVIJ-UHFFFAOYSA-N 0.000 description 3
- 210000003608 fece Anatomy 0.000 description 3
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- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
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- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 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
- 229910052760 oxygen Inorganic materials 0.000 description 3
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- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 2
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 2
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/966,511 US7030203B2 (en) | 2001-09-28 | 2001-09-28 | Water-in-oil emulsions with ethylene oxide groups, compositions, and methods |
Publications (1)
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| ZA200403168B true ZA200403168B (en) | 2005-01-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| ZA200403168A ZA200403168B (en) | 2001-09-28 | 2004-04-26 | Water-in-oil emulsions comprising vinyl polymers carrying ethylene oxide groups in side chains, compositions and methods. |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7030203B2 (es) |
| EP (3) | EP1949888B1 (es) |
| JP (1) | JP4598393B2 (es) |
| KR (1) | KR100915649B1 (es) |
| CN (2) | CN1697662A (es) |
| AT (2) | ATE548018T1 (es) |
| AU (1) | AU2002319793B2 (es) |
| BR (1) | BR0212867A (es) |
| CA (2) | CA2461623C (es) |
| DE (1) | DE60225036T2 (es) |
| ES (1) | ES2300456T3 (es) |
| MX (1) | MX247922B (es) |
| TW (1) | TWI333859B (es) |
| WO (1) | WO2003028767A2 (es) |
| ZA (1) | ZA200403168B (es) |
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| JP4836793B2 (ja) * | 2003-05-15 | 2011-12-14 | アーチ ユーケイ バイオサイドズ リミテッド | 組成物及びその使用（１） |
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| US7030203B2 (en) | 2001-09-28 | 2006-04-18 | 3M Innovative Properties Company | Water-in-oil emulsions with ethylene oxide groups, compositions, and methods |
| US6951642B2 (en) | 2001-09-28 | 2005-10-04 | 3M Innovative Properties Company | Water-in-oil emulsions with anionic groups, compositions, and methods |
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-
2001
- 2001-09-28 US US09/966,511 patent/US7030203B2/en not_active Expired - Lifetime
-
2002
- 2002-08-08 EP EP08151309A patent/EP1949888B1/en not_active Expired - Lifetime
- 2002-08-08 BR BR0212867-5A patent/BR0212867A/pt not_active Application Discontinuation
- 2002-08-08 ES ES02750460T patent/ES2300456T3/es not_active Expired - Lifetime
- 2002-08-08 CA CA2461623A patent/CA2461623C/en not_active Expired - Fee Related
- 2002-08-08 WO PCT/US2002/025260 patent/WO2003028767A2/en active IP Right Grant
- 2002-08-08 CA CA 2722319 patent/CA2722319C/en not_active Expired - Fee Related
- 2002-08-08 KR KR1020047004438A patent/KR100915649B1/ko not_active IP Right Cessation
- 2002-08-08 AT AT08151309T patent/ATE548018T1/de active
- 2002-08-08 AT AT02750460T patent/ATE385773T1/de not_active IP Right Cessation
- 2002-08-08 MX MXPA04002779 patent/MX247922B/es active IP Right Grant
- 2002-08-08 JP JP2003532096A patent/JP4598393B2/ja not_active Expired - Fee Related
- 2002-08-08 AU AU2002319793A patent/AU2002319793B2/en not_active Ceased
- 2002-08-08 CN CNA028191439A patent/CN1697662A/zh active Pending
- 2002-08-08 DE DE60225036T patent/DE60225036T2/de not_active Expired - Lifetime
- 2002-08-08 EP EP10185881.9A patent/EP2308456B1/en not_active Expired - Lifetime
- 2002-08-08 EP EP02750460A patent/EP1436010B1/en not_active Expired - Lifetime
- 2002-08-08 CN CN201110173896.XA patent/CN102344633B/zh not_active Expired - Fee Related
- 2002-09-09 TW TW091120441A patent/TWI333859B/zh not_active IP Right Cessation
-
2004
- 2004-04-26 ZA ZA200403168A patent/ZA200403168B/en unknown
-
2005
- 2005-10-21 US US11/256,135 patent/US8026327B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2722319C (en) | 2015-04-28 |
| KR100915649B1 (ko) | 2009-09-04 |
| ES2300456T3 (es) | 2008-06-16 |
| ATE548018T1 (de) | 2012-03-15 |
| CA2461623C (en) | 2011-01-11 |
| KR20040037144A (ko) | 2004-05-04 |
| EP1436010A2 (en) | 2004-07-14 |
| CA2461623A1 (en) | 2003-04-10 |
| EP1949888A1 (en) | 2008-07-30 |
| US8026327B2 (en) | 2011-09-27 |
| CN102344633A (zh) | 2012-02-08 |
| EP2308456A1 (en) | 2011-04-13 |
| BR0212867A (pt) | 2004-09-14 |
| MXPA04002779A (es) | 2004-07-29 |
| US20060034798A1 (en) | 2006-02-16 |
| JP2005512968A (ja) | 2005-05-12 |
| EP1436010B1 (en) | 2008-02-13 |
| DE60225036D1 (de) | 2008-03-27 |
| TWI333859B (en) | 2010-12-01 |
| ATE385773T1 (de) | 2008-03-15 |
| CN1697662A (zh) | 2005-11-16 |
| MX247922B (es) | 2007-08-08 |
| WO2003028767A3 (en) | 2003-06-19 |
| EP2308456B1 (en) | 2016-10-12 |
| DE60225036T2 (de) | 2009-02-19 |
| US7030203B2 (en) | 2006-04-18 |
| WO2003028767A2 (en) | 2003-04-10 |
| CA2722319A1 (en) | 2003-04-10 |
| JP4598393B2 (ja) | 2010-12-15 |
| CN102344633B (zh) | 2014-11-05 |
| US20030149106A1 (en) | 2003-08-07 |
| AU2002319793B2 (en) | 2008-07-10 |
| EP1949888B1 (en) | 2012-03-07 |
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