CA2746326C - Method for preparing personal care composition comprising surfactant and high melting point fatty compound - Google Patents
Method for preparing personal care composition comprising surfactant and high melting point fatty compound Download PDFInfo
- Publication number
- CA2746326C CA2746326C CA2746326A CA2746326A CA2746326C CA 2746326 C CA2746326 C CA 2746326C CA 2746326 A CA2746326 A CA 2746326A CA 2746326 A CA2746326 A CA 2746326A CA 2746326 C CA2746326 C CA 2746326C
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- CA
- Canada
- Prior art keywords
- melting point
- composition
- high melting
- oil phase
- point fatty
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 150
- 150000001875 compounds Chemical class 0.000 title claims abstract description 89
- 238000002844 melting Methods 0.000 title claims abstract description 87
- 230000008018 melting Effects 0.000 title claims abstract description 87
- 238000000034 method Methods 0.000 title claims abstract description 52
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 35
- 239000012071 phase Substances 0.000 claims abstract description 83
- 239000003093 cationic surfactant Substances 0.000 claims abstract description 54
- 239000008346 aqueous phase Substances 0.000 claims abstract description 52
- 239000000839 emulsion Substances 0.000 claims abstract description 34
- 239000008365 aqueous carrier Substances 0.000 claims abstract description 25
- 238000002156 mixing Methods 0.000 claims abstract description 21
- 239000011159 matrix material Substances 0.000 claims description 20
- 239000003921 oil Substances 0.000 description 62
- 230000003750 conditioning effect Effects 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 230000008901 benefit Effects 0.000 description 43
- 229920001296 polysiloxane Polymers 0.000 description 34
- 239000000047 product Substances 0.000 description 25
- 239000000499 gel Substances 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- -1 amine salt Chemical class 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 16
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 14
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 14
- 239000004615 ingredient Substances 0.000 description 13
- 229920013822 aminosilicone Polymers 0.000 description 11
- 150000002191 fatty alcohols Chemical class 0.000 description 11
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 231100000640 hair analysis Toxicity 0.000 description 9
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000003945 anionic surfactant Substances 0.000 description 8
- 229960000541 cetyl alcohol Drugs 0.000 description 8
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 8
- 239000003755 preservative agent Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 229920006318 anionic polymer Polymers 0.000 description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 description 7
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000013019 agitation Methods 0.000 description 6
- 150000003863 ammonium salts Chemical class 0.000 description 6
- YSJGOMATDFSEED-UHFFFAOYSA-M behentrimonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCCCCC[N+](C)(C)C YSJGOMATDFSEED-UHFFFAOYSA-M 0.000 description 6
- 239000002304 perfume Substances 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 206010019049 Hair texture abnormal Diseases 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000010696 ester oil Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- MRAMPOPITCOOIN-VIFPVBQESA-N (2r)-n-(3-ethoxypropyl)-2,4-dihydroxy-3,3-dimethylbutanamide Chemical compound CCOCCCNC(=O)[C@H](O)C(C)(C)CO MRAMPOPITCOOIN-VIFPVBQESA-N 0.000 description 4
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 4
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 4
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229940008099 dimethicone Drugs 0.000 description 4
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 4
- 229960000735 docosanol Drugs 0.000 description 4
- 239000004220 glutamic acid Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229940101267 panthenol Drugs 0.000 description 4
- 229940023735 panthenyl ethyl ether Drugs 0.000 description 4
- 235000020957 pantothenol Nutrition 0.000 description 4
- 239000011619 pantothenol Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000005233 alkylalcohol group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 3
- 238000003892 spreading Methods 0.000 description 3
- 230000007480 spreading Effects 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AKDICWVOBJJFPB-UHFFFAOYSA-N N-[3-(dimethylamino)propyl]octadecanamide sulfuric acid Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)NCCCN(C)C.S(=O)(=O)(O)O AKDICWVOBJJFPB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000002511 behenyl group Chemical group [H]C([*])([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])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])[H] 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000008406 cosmetic ingredient Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZCPCLAPUXMZUCD-UHFFFAOYSA-M dihexadecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCC ZCPCLAPUXMZUCD-UHFFFAOYSA-M 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- KKBOOQDFOWZSDC-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCN(CC)CC KKBOOQDFOWZSDC-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 238000000518 rheometry Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 108010064851 Plant Proteins Proteins 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- LPGFSDGXTDNTCB-UHFFFAOYSA-N [3-(16-methylheptadecanoyloxy)-2,2-bis(16-methylheptadecanoyloxymethyl)propyl] 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCC(C)C)(COC(=O)CCCCCCCCCCCCCCC(C)C)COC(=O)CCCCCCCCCCCCCCC(C)C LPGFSDGXTDNTCB-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229960002788 cetrimonium chloride Drugs 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229940086555 cyclomethicone Drugs 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 229940073551 distearyldimonium chloride Drugs 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- QIVLQXGSQSFTIF-UHFFFAOYSA-M docosyl(trimethyl)azanium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCCCCCCCCCCCCCCCCCCCCC[N+](C)(C)C QIVLQXGSQSFTIF-UHFFFAOYSA-M 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Chemical class 0.000 description 1
- 229930195729 fatty acid Chemical class 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000005908 glyceryl ester group Chemical group 0.000 description 1
- 230000003699 hair surface Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- ZCTXEAQXZGPWFG-UHFFFAOYSA-N imidurea Chemical compound O=C1NC(=O)N(CO)C1NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO ZCTXEAQXZGPWFG-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- 229940049292 n-(3-(dimethylamino)propyl)octadecanamide Drugs 0.000 description 1
- KHPAAXRLVYMUHU-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)NCCN(CC)CC KHPAAXRLVYMUHU-UHFFFAOYSA-N 0.000 description 1
- UIUQXDQHAWBLOW-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]icosanamide Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)NCCN(CC)CC UIUQXDQHAWBLOW-UHFFFAOYSA-N 0.000 description 1
- NCBXVQKSCKRNTB-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]icosanamide Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)NCCN(C)C NCBXVQKSCKRNTB-UHFFFAOYSA-N 0.000 description 1
- DYAVLIWAWOZKBI-UHFFFAOYSA-N n-[3-(diethylamino)propyl]hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(=O)NCCCN(CC)CC DYAVLIWAWOZKBI-UHFFFAOYSA-N 0.000 description 1
- OVCKOYOTKXBZKK-UHFFFAOYSA-N n-[3-(diethylamino)propyl]icosanamide Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)NCCCN(CC)CC OVCKOYOTKXBZKK-UHFFFAOYSA-N 0.000 description 1
- KUIOQEAUQATWEY-UHFFFAOYSA-N n-[3-(diethylamino)propyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCCN(CC)CC KUIOQEAUQATWEY-UHFFFAOYSA-N 0.000 description 1
- MNAZHGAWPCLLGX-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)NCCCN(C)C MNAZHGAWPCLLGX-UHFFFAOYSA-N 0.000 description 1
- BDHJUCZXTYXGCZ-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(=O)NCCCN(C)C BDHJUCZXTYXGCZ-UHFFFAOYSA-N 0.000 description 1
- HJXPIPGLPXVLGN-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]icosanamide Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)NCCCN(C)C HJXPIPGLPXVLGN-UHFFFAOYSA-N 0.000 description 1
- WWVIUVHFPSALDO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCCN(C)C WWVIUVHFPSALDO-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Chemical group 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229940032160 stearamidoethyl diethylamine Drugs 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 229940043810 zinc pyrithione Drugs 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/342—Alcohols having more than seven atoms in an unbroken chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
- Colloid Chemistry (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12086908P | 2008-12-09 | 2008-12-09 | |
| US61/120,869 | 2008-12-09 | ||
| PCT/US2009/067236 WO2010077706A2 (en) | 2008-12-09 | 2009-12-09 | Method for preparing personal care composition comprising surfactant and high melting point fatty compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2746326A1 CA2746326A1 (en) | 2010-07-08 |
| CA2746326C true CA2746326C (en) | 2014-08-12 |
Family
ID=42231320
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2746326A Active CA2746326C (en) | 2008-12-09 | 2009-12-09 | Method for preparing personal care composition comprising surfactant and high melting point fatty compound |
| CA2746293A Active CA2746293C (en) | 2008-12-09 | 2009-12-09 | Method for preparing personal care composition comprising surfactant and high melting point fatty compound |
| CA2746291A Active CA2746291C (en) | 2008-12-09 | 2009-12-09 | Method for preparing personal care composition comprising surfactant and high melting point fatty compound |
| CA2799695A Abandoned CA2799695A1 (en) | 2008-12-09 | 2009-12-09 | Method for preparing personal care composition comprising surfactant and high melting fatty compound |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2746293A Active CA2746293C (en) | 2008-12-09 | 2009-12-09 | Method for preparing personal care composition comprising surfactant and high melting point fatty compound |
| CA2746291A Active CA2746291C (en) | 2008-12-09 | 2009-12-09 | Method for preparing personal care composition comprising surfactant and high melting point fatty compound |
| CA2799695A Abandoned CA2799695A1 (en) | 2008-12-09 | 2009-12-09 | Method for preparing personal care composition comprising surfactant and high melting fatty compound |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US20100143281A1 (OSRAM) |
| EP (4) | EP2355784A2 (OSRAM) |
| JP (8) | JP5718243B2 (OSRAM) |
| CN (5) | CN102245162B (OSRAM) |
| AU (3) | AU2009333471A1 (OSRAM) |
| BR (3) | BRPI0922535B1 (OSRAM) |
| CA (4) | CA2746326C (OSRAM) |
| MX (4) | MX340284B (OSRAM) |
| WO (4) | WO2010077705A2 (OSRAM) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9968535B2 (en) * | 2007-10-26 | 2018-05-15 | The Procter & Gamble Company | Personal care compositions comprising undecyl sulfates |
| CN104083290B (zh) | 2008-06-25 | 2018-02-16 | 宝洁公司 | 具有较高屈服点和较高的脂肪族化合物至凝胶基质转化率的毛发调理组合物 |
| EP2293766A2 (en) * | 2008-06-25 | 2011-03-16 | The Procter & Gamble Company | Hair conditioning composition containing behenyl trimethyl ammonium chloride, and having higher yield point |
| MX2011012790A (es) * | 2009-06-04 | 2011-12-16 | Procter & Gamble | Sistema de productos multiples para el pelo. |
| EP2440646B1 (en) * | 2009-06-08 | 2013-03-06 | The Procter & Gamble Company | Process for making a cleaning composition employing direct incorporation of concentrated surfactants |
| EP2563779A1 (en) * | 2009-11-06 | 2013-03-06 | Bayer CropScience AG | Insecticidal arylpyrroline compounds |
| CN103747778B (zh) * | 2011-06-09 | 2016-06-08 | 宝洁公司 | 制备包含单烷基胺双表面活性剂体系和可溶性盐的个人护理组合物的方法 |
| JP5912183B2 (ja) * | 2011-09-15 | 2016-04-27 | ザ プロクター アンド ギャンブル カンパニー | 界面活性剤系及び高融点脂肪化合物を含むパーソナルケア組成物の調製方法 |
| US20150125416A1 (en) | 2011-12-20 | 2015-05-07 | Conopco, Inc., d/h/a UNILEVER | Method for production of structured liquid and structured liquid |
| MX356597B (es) * | 2013-02-08 | 2018-06-04 | Procter & Gamble | Metodo para preparar composiciones para el cuidado del cabello que comprende una etapa de agregar perfumes y/o siliconas antes de agentes anticaspa. |
| CN106860037B (zh) * | 2013-02-08 | 2021-01-01 | 宝洁公司 | 包括控制温度以加入去头皮屑剂的步骤的制备毛发护理组合物的方法 |
| JP6291031B2 (ja) | 2013-04-05 | 2018-03-14 | ザ プロクター アンド ギャンブル カンパニー | 予め乳化させた製剤を含むパーソナルケア組成物 |
| US9974718B2 (en) | 2014-02-06 | 2018-05-22 | The Procter & Gamble Company | Method for preparing hair care compositions comprising a step of adding perfumes and/or silicones before antidandruff agents |
| US10226404B2 (en) | 2014-02-06 | 2019-03-12 | The Procter And Gamble Company | Method for preparing antidandruff hair care compositions comprising a step of injecting antidandruff agents, perfumes and/or silicones |
| WO2015195542A1 (en) | 2014-06-16 | 2015-12-23 | The Procter & Gamble Company | Method of treating hair with a concentrated conditioner |
| EP3154506A1 (en) | 2014-06-16 | 2017-04-19 | The Procter & Gamble Company | Method of treating hair with a concentrated conditioner |
| CN107072927A (zh) * | 2014-06-16 | 2017-08-18 | 宝洁公司 | 利用浓缩型调理剂处理毛发的方法 |
| US10806688B2 (en) | 2014-10-03 | 2020-10-20 | The Procter And Gamble Company | Method of achieving improved volume and combability using an anti-dandruff personal care composition comprising a pre-emulsified formulation |
| US9993404B2 (en) | 2015-01-15 | 2018-06-12 | The Procter & Gamble Company | Translucent hair conditioning composition |
| CN107847767A (zh) | 2015-04-23 | 2018-03-27 | 宝洁公司 | 毛发护理调理组合物 |
| US10285925B2 (en) | 2015-12-15 | 2019-05-14 | The Procter & Gamble Company | Method of treating hair |
| US10265251B2 (en) | 2015-12-15 | 2019-04-23 | The Procter And Gamble Company | Method of treating hair |
| CN108367168A (zh) | 2015-12-15 | 2018-08-03 | 宝洁公司 | 处理毛发的方法 |
| US10124951B2 (en) | 2015-12-15 | 2018-11-13 | The Procter And Gamble Company | Method of treating hair |
| US10265256B2 (en) | 2015-12-15 | 2019-04-23 | The Procter And Gamble Company | Method of treating hair |
| EP3389793B1 (en) | 2015-12-15 | 2020-06-17 | The Procter and Gamble Company | Method of treating hair |
| US10294013B2 (en) | 2015-12-21 | 2019-05-21 | The Procter And Gamble Plaza | Package to dispense a foaming composition |
| EP3405168B1 (en) | 2016-01-20 | 2025-01-22 | The Procter & Gamble Company | Hair conditioning composition comprising monoalkyl glyceryl ether |
| US10835480B2 (en) | 2016-04-22 | 2020-11-17 | The Procter And Gamble Company | Method of forming a silicone layer |
| EP3445327A1 (en) | 2016-04-22 | 2019-02-27 | The Procter and Gamble Company | Method of forming a silicone layer |
| BR112019009550B1 (pt) * | 2017-04-13 | 2023-01-31 | The Procter & Gamble Company | Composição de produto compreendendo uma partícula discreta e uma composição-base aquosa |
| EP3810315B1 (en) * | 2018-06-22 | 2025-11-26 | Kenvue Brands LLC | Process for formation of emulsion containing liquid crystal structure |
| US11931441B2 (en) | 2018-10-10 | 2024-03-19 | The Procter & Gamble Company | Personal care product customized by discrete particles and method of apply thereof |
| WO2020097406A1 (en) | 2018-11-08 | 2020-05-14 | The Procter & Gamble Company | Low shear stress conditioner composition with spherical gel network vesicles |
| CN119409936B (zh) * | 2025-01-03 | 2025-07-04 | 成都纺织高等专科学校 | 一种阳离子型聚氨酯防水剂分散体的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4275055A (en) | 1979-06-22 | 1981-06-23 | Conair Corporation | Hair conditioner having a stabilized, pearlescent effect |
| DE19829647A1 (de) * | 1998-07-02 | 2000-01-13 | Wella Ag | Verfahren zur Herstellung von wäßrigen Emulsionen oder Suspensionen |
| AU2309499A (en) * | 1999-01-04 | 2000-07-24 | Procter & Gamble Company, The | Hair conditioning layered gel composition containing a high melting point compound |
| AU5704899A (en) * | 1999-09-03 | 2001-04-10 | Procter & Gamble Company, The | A process for forming a hair care composition and a composition formed by same |
| US6849252B1 (en) * | 1999-09-03 | 2005-02-01 | The Procter & Gamble Company | Hair care composition comprising a polypropylene glycol |
| DE10006673C1 (de) * | 2000-02-15 | 2001-09-27 | Basf Coatings Ag | Wäßrige Pulverlackdispersionen (Pulverslurries) und Verfahren zu ihrer Herstellung |
| US8349301B2 (en) * | 2002-06-04 | 2013-01-08 | The Procter & Gamble Company | Shampoo containing a gel network |
| US20040116539A1 (en) * | 2002-12-16 | 2004-06-17 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Late variant addition process for personal care products |
| JP2005255627A (ja) * | 2004-03-12 | 2005-09-22 | Kanebo Cosmetics Inc | 毛髪化粧料 |
| BRPI0516600A (pt) * | 2004-10-13 | 2008-09-16 | Procter & Gamble | composição para condicionamento dos cabelos compreendendo um tensoativo catiÈnico à base de sal de amÈnio alquil diquaternizado |
| US20070014823A1 (en) * | 2005-07-12 | 2007-01-18 | The Procter & Gamble Company | Multi phase personal care composition comprising compositions having similar rheology profile in different phases |
| WO2008021893A1 (en) * | 2006-08-08 | 2008-02-21 | The Procter & Gamble Company | Fabric enhancing compositions comprising nano-sized particles and anionic detergent carry over tollerance |
| EP2293766A2 (en) * | 2008-06-25 | 2011-03-16 | The Procter & Gamble Company | Hair conditioning composition containing behenyl trimethyl ammonium chloride, and having higher yield point |
| CN104083290B (zh) * | 2008-06-25 | 2018-02-16 | 宝洁公司 | 具有较高屈服点和较高的脂肪族化合物至凝胶基质转化率的毛发调理组合物 |
| AU2009312928B2 (en) * | 2008-11-07 | 2013-05-23 | Unilever Plc | Conditioning shampoo composition comprising an aqueous conditioning- gel |
-
2009
- 2009-12-09 BR BRPI0922535-8A patent/BRPI0922535B1/pt active IP Right Grant
- 2009-12-09 JP JP2011539804A patent/JP5718243B2/ja active Active
- 2009-12-09 CN CN200980149354.XA patent/CN102245162B/zh active Active
- 2009-12-09 US US12/633,952 patent/US20100143281A1/en not_active Abandoned
- 2009-12-09 WO PCT/US2009/067235 patent/WO2010077705A2/en not_active Ceased
- 2009-12-09 CN CN201710009500.5A patent/CN107028778A/zh active Pending
- 2009-12-09 JP JP2011539805A patent/JP5718244B2/ja active Active
- 2009-12-09 US US12/633,965 patent/US20100143425A1/en not_active Abandoned
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- 2009-12-09 BR BRPI0922537A patent/BRPI0922537A2/pt not_active Application Discontinuation
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- 2009-12-09 EP EP09793380A patent/EP2355784A2/en not_active Withdrawn
- 2009-12-09 US US12/633,987 patent/US20100143282A1/en not_active Abandoned
- 2009-12-09 CN CN200980149352.0A patent/CN102245161B/zh active Active
- 2009-12-09 CA CA2746326A patent/CA2746326C/en active Active
- 2009-12-09 US US12/633,939 patent/US20100143280A1/en not_active Abandoned
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- 2009-12-09 CA CA2746291A patent/CA2746291C/en active Active
- 2009-12-09 CA CA2799695A patent/CA2799695A1/en not_active Abandoned
- 2009-12-09 MX MX2011006125A patent/MX2011006125A/es active IP Right Grant
- 2009-12-09 JP JP2011539802A patent/JP5718241B2/ja active Active
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2014
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- 2014-12-01 JP JP2014243069A patent/JP2015110568A/ja active Pending
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