JP2008516041A5 - - Google Patents
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- Publication number
- JP2008516041A5 JP2008516041A5 JP2007535267A JP2007535267A JP2008516041A5 JP 2008516041 A5 JP2008516041 A5 JP 2008516041A5 JP 2007535267 A JP2007535267 A JP 2007535267A JP 2007535267 A JP2007535267 A JP 2007535267A JP 2008516041 A5 JP2008516041 A5 JP 2008516041A5
- Authority
- JP
- Japan
- Prior art keywords
- poly
- block
- copolymer
- methacrylate
- core
- 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.)
- Granted
Links
- 229920001400 block copolymer Polymers 0.000 claims description 44
- 125000005647 linker group Chemical group 0.000 claims description 39
- 230000002209 hydrophobic effect Effects 0.000 claims description 31
- 238000006116 polymerization reaction Methods 0.000 claims description 25
- 125000000524 functional group Chemical group 0.000 claims description 24
- 239000003205 fragrance Substances 0.000 claims description 23
- 229920001577 copolymer Polymers 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- 229920002125 Sokalan® Polymers 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- -1 poly La Kuchido Polymers 0.000 claims description 12
- 239000000796 flavoring agent Substances 0.000 claims description 10
- 235000019634 flavors Nutrition 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000002088 nanocapsule Substances 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 4
- 239000012437 perfumed product Substances 0.000 claims description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 4
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- 238000005096 rolling process Methods 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 claims description 2
- 229920002873 Polyethylenimine Polymers 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 229920000765 poly(2-oxazolines) Polymers 0.000 claims description 2
- 229920001308 poly(aminoacid) Polymers 0.000 claims description 2
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 2
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 claims description 2
- FXPQHXMQGQZQOM-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate;methoxymethane Chemical compound COC.CC(=C)C(=O)OCCOCCO FXPQHXMQGQZQOM-UHFFFAOYSA-N 0.000 claims 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 claims 1
- 229920002732 Polyanhydride Polymers 0.000 claims 1
- RNTIBYGPJVJCCJ-UHFFFAOYSA-N n,n-dimethylmethanamine;ethyl 2-methylprop-2-enoate Chemical compound CN(C)C.CCOC(=O)C(C)=C RNTIBYGPJVJCCJ-UHFFFAOYSA-N 0.000 claims 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 claims 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 claims 1
- 229920002627 poly(phosphazenes) Polymers 0.000 claims 1
- 229920001610 polycaprolactone Polymers 0.000 claims 1
- 239000004632 polycaprolactone Substances 0.000 claims 1
- 229920001451 polypropylene glycol Polymers 0.000 claims 1
- 229920001296 polysiloxane Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000003999 initiator Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000000178 monomer Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 9
- 239000002775 capsule Substances 0.000 description 9
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 8
- 238000005538 encapsulation Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 4
- 229920000736 dendritic polymer Polymers 0.000 description 4
- 239000002979 fabric softener Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- GURVPPWCMAEKNI-UHFFFAOYSA-N 1-pyridin-2-ylbutan-1-imine Chemical compound CCCC(=N)C1=CC=CC=N1 GURVPPWCMAEKNI-UHFFFAOYSA-N 0.000 description 3
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 3
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000000975 bioactive effect Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229940043350 citral Drugs 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 0 *C(C(OCCN(*)*)=N)=C Chemical compound *C(C(OCCN(*)*)=N)=C 0.000 description 2
- UWOVWIIOKHRNKU-UHFFFAOYSA-N 2,6-diphenyl-4-(2,4,6-triphenylpyridin-1-ium-1-yl)phenolate Chemical compound [O-]C1=C(C=2C=CC=CC=2)C=C([N+]=2C(=CC(=CC=2C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 UWOVWIIOKHRNKU-UHFFFAOYSA-N 0.000 description 2
- KZZASWGRLOTITL-UHFFFAOYSA-N 4-cyclohexyl-2-methylbutan-2-ol Chemical compound CC(C)(O)CCC1CCCCC1 KZZASWGRLOTITL-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- TWXUTZNBHUWMKJ-UHFFFAOYSA-N Allyl cyclohexylpropionate Chemical compound C=CCOC(=O)CCC1CCCCC1 TWXUTZNBHUWMKJ-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 229940007550 benzyl acetate Drugs 0.000 description 2
- 239000012867 bioactive agent Substances 0.000 description 2
- QAWBXZYPFCFQLA-UHFFFAOYSA-N butanoyl bromide Chemical compound CCCC(Br)=O QAWBXZYPFCFQLA-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229920000587 hyperbranched polymer Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 230000002688 persistence Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 2
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- VIINAUVGZZLXGK-GGTVIOIRSA-N (2E)-3,7-dimethylocta-2,6-dien-1-ol Chemical compound CC(C)=CCC\C(C)=C\CO.CC(C)=CCC\C(C)=C\CO VIINAUVGZZLXGK-GGTVIOIRSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 1
- OFHHDSQXFXLTKC-UHFFFAOYSA-N 10-undecenal Chemical compound C=CCCCCCCCCC=O OFHHDSQXFXLTKC-UHFFFAOYSA-N 0.000 description 1
- IVZBZNYTLBRQHT-UHFFFAOYSA-N 2,2-dibromopropanoyl bromide Chemical group CC(Br)(Br)C(Br)=O IVZBZNYTLBRQHT-UHFFFAOYSA-N 0.000 description 1
- HGDVHRITTGWMJK-UHFFFAOYSA-N 2,6-dimethylheptan-2-ol Chemical compound CC(C)CCCC(C)(C)O HGDVHRITTGWMJK-UHFFFAOYSA-N 0.000 description 1
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 description 1
- YOCIJWAHRAJQFT-UHFFFAOYSA-N 2-bromo-2-methylpropanoyl bromide Chemical compound CC(C)(Br)C(Br)=O YOCIJWAHRAJQFT-UHFFFAOYSA-N 0.000 description 1
- ILLHORFDXDLILE-UHFFFAOYSA-N 2-bromopropanoyl bromide Chemical compound CC(Br)C(Br)=O ILLHORFDXDLILE-UHFFFAOYSA-N 0.000 description 1
- MWYGSCHWFNRSET-UHFFFAOYSA-N 2-pentylcyclopentan-1-ol Chemical compound CCCCCC1CCCC1O MWYGSCHWFNRSET-UHFFFAOYSA-N 0.000 description 1
- WTPYRCJDOZVZON-UHFFFAOYSA-N 3,5,5-Trimethylhexanal Chemical compound O=CCC(C)CC(C)(C)C WTPYRCJDOZVZON-UHFFFAOYSA-N 0.000 description 1
- MBZRJSQZCBXRGK-UHFFFAOYSA-N 4-tert-Butylcyclohexyl acetate Chemical compound CC(=O)OC1CCC(C(C)(C)C)CC1 MBZRJSQZCBXRGK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229920005605 branched copolymer Polymers 0.000 description 1
- 150000001649 bromium compounds Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000012482 calibration solution Substances 0.000 description 1
- HDPRHRZFFPXZIL-UHFFFAOYSA-N calix[8]arene Chemical compound OC1=C(CC=2C(=C(CC=3C(=C(CC=4C(=C(CC=5C(=C(CC=6C(=C(CC=7C(=C(C8)C=CC=7)O)C=CC=6)O)C=CC=5)O)C=CC=4)O)C=CC=3)O)C=CC=2)O)C=CC=C1CC1=C(O)C8=CC=C1 HDPRHRZFFPXZIL-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229920000359 diblock copolymer Polymers 0.000 description 1
- YSCOODQOCWOXNL-UHFFFAOYSA-N diethylamino 2-methylprop-2-enoate Chemical compound CCN(CC)OC(=O)C(C)=C YSCOODQOCWOXNL-UHFFFAOYSA-N 0.000 description 1
- HOSXICNCYBUYAW-UHFFFAOYSA-N dimethylamino prop-2-enoate Chemical compound CN(C)OC(=O)C=C HOSXICNCYBUYAW-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AAYYTNPAPOADFH-SOFGYWHQSA-N ethyl (e)-2,4-dimethylpent-2-enoate Chemical compound CCOC(=O)C(\C)=C\C(C)C AAYYTNPAPOADFH-SOFGYWHQSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000004676 glycans Polymers 0.000 description 1
- 125000005283 haloketone group Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000003473 lipid group Chemical group 0.000 description 1
- 150000002634 lipophilic molecules Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000302 molecular modelling Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000012705 nitroxide-mediated radical polymerization Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000008257 shaving cream Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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| EP04104955 | 2004-10-08 | ||
| PCT/IB2005/003023 WO2006038110A2 (en) | 2004-10-08 | 2005-10-10 | Amphiphilic star block copolymers |
Publications (3)
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| JP2008516041A JP2008516041A (ja) | 2008-05-15 |
| JP2008516041A5 true JP2008516041A5 (https=) | 2012-01-26 |
| JP5090915B2 JP5090915B2 (ja) | 2012-12-05 |
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| JP2007535267A Expired - Fee Related JP5090915B2 (ja) | 2004-10-08 | 2005-10-10 | 両親媒性スターブロックポリマー |
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| US (1) | US20070160561A1 (https=) |
| EP (1) | EP1814924A2 (https=) |
| JP (1) | JP5090915B2 (https=) |
| CN (1) | CN101035823B (https=) |
| BR (1) | BRPI0516259A (https=) |
| MX (1) | MX301374B (https=) |
| RU (1) | RU2007117150A (https=) |
| WO (1) | WO2006038110A2 (https=) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE502006007655D1 (de) | 2005-10-25 | 2010-09-23 | Evonik Degussa Gmbh | Präparate umfassend hyperverzweigte polymere |
| DE102005051342A1 (de) * | 2005-10-25 | 2007-04-26 | Goldschmidt Gmbh | Verkapselung und kontrollierte Freisetzung biologisch aktiver Wirkstoffe mit enzymatisch abbaubaren hyperverzweigten Trägerpolymeren |
| DE102006046073A1 (de) * | 2006-09-27 | 2008-04-03 | Henkel Kgaa | Hyperverzweigte Polymere zur hygienischen Ausrüstung |
| WO2008079677A2 (en) * | 2006-12-20 | 2008-07-03 | Arkema Inc. | Polymer encapsulation and/or binding |
| EP1982698A1 (de) * | 2007-04-18 | 2008-10-22 | Evonik Degussa GmbH | Präparate zur gesteuerten Freisetzung von bioaktiven Naturstoffen |
| DE102008024868A1 (de) * | 2008-05-23 | 2009-11-26 | Merck Patent Gmbh | Polymerisationsverfahren zur Herstellung von Kern-Hülle-Partikeln |
| DE102008034106A1 (de) * | 2008-07-21 | 2010-01-28 | Evonik Röhm Gmbh | Blockcopolymere auf (Meth)acrylatbasis mit A-P-Struktur |
| US8815971B2 (en) * | 2008-12-22 | 2014-08-26 | ATRP Solutions, Inc. | Control over controlled radical polymerization processes |
| US8822610B2 (en) | 2008-12-22 | 2014-09-02 | ATRP Solutions, Inc. | Control over controlled radical polymerization processes |
| US8569421B2 (en) | 2009-04-23 | 2013-10-29 | ATRP Solutions, Inc. | Star macromolecules for personal and home care |
| US8173750B2 (en) | 2009-04-23 | 2012-05-08 | ATRP Solutions, Inc. | Star macromolecules for personal and home care |
| US9783628B2 (en) | 2009-04-23 | 2017-10-10 | ATRP Solutions, Inc. | Dual-mechanism thickening agents for hydraulic fracturing fluids |
| UA105793C2 (uk) | 2009-05-11 | 2014-06-25 | Басф Се | Гіперрозгалужені полікарбонати для солюбілізації важкорозчинних діючих речовин |
| US8013065B2 (en) * | 2009-06-09 | 2011-09-06 | International Business Machines Corporation | Methods for making multi-branched polymers |
| WO2011073222A2 (de) * | 2009-12-18 | 2011-06-23 | Basf Se | Hyperverzweigte polyester mit hydrophobem kern zur solubilisierung schwerlöslicher wirkstoffe |
| WO2011101757A1 (en) * | 2010-02-17 | 2011-08-25 | Firmenich Sa | Cyclic oxy compounds as perfuming ingredients |
| US9186642B2 (en) | 2010-04-28 | 2015-11-17 | The Procter & Gamble Company | Delivery particle |
| US9993793B2 (en) | 2010-04-28 | 2018-06-12 | The Procter & Gamble Company | Delivery particles |
| US9587064B2 (en) | 2010-12-08 | 2017-03-07 | ATRP Solutions, Inc. | Salt-tolerant star macromolecules |
| EP2678042B1 (en) * | 2011-02-23 | 2018-05-09 | The Board of Trustees of the University of Illionis | Amphiphilic dendron-coils, micelles thereof and uses |
| WO2012138710A2 (en) | 2011-04-07 | 2012-10-11 | The Procter & Gamble Company | Personal cleansing compositions with increased deposition of polyacrylate microcapsules |
| WO2012138696A2 (en) | 2011-04-07 | 2012-10-11 | The Procter & Gamble Company | Shampoo compositions with increased deposition of polyacrylate microcapsules |
| WO2012138690A2 (en) | 2011-04-07 | 2012-10-11 | The Procter & Gamble Company | Conditioner compositions with increased deposition of polyacrylate microcapsules |
| EP2725053B1 (en) * | 2011-06-23 | 2016-02-10 | Shimadzu Corporation | Branched amphipathic block polymer and molecular aggregate and drug delivery system using same |
| US8445577B2 (en) * | 2011-07-25 | 2013-05-21 | Iowa State University Research Foundation, Inc. | Amphiphilic multi-arm copolymers and nanomaterials derived therefrom |
| JP6294885B2 (ja) | 2012-08-30 | 2018-03-14 | エーティーアールピー ソリューションズ インコーポレイテッドＡＴＲＰ Ｓｏｌｕｔｉｏｎｓ，Ｉｎｃ． | 星形高分子、星形高分子組成物および星形高分子の製造方法 |
| WO2014038558A1 (ja) * | 2012-09-04 | 2014-03-13 | 株式会社 島津製作所 | 分岐型両親媒性ブロックポリマーを用いた分子集合体及び薬剤搬送システム |
| CN105263978B (zh) | 2013-02-04 | 2018-04-17 | Atrp解决方案公司 | 耐盐星形大分子 |
| CN103214637B (zh) * | 2013-04-23 | 2013-12-04 | 何涛 | 一种超支化聚合物纳米缓释材料及其制备方法 |
| JP6198713B2 (ja) * | 2013-12-20 | 2017-09-20 | ザ リージェンツ オブ ザ ユニバーシティー オブ カリフォルニア | 接合部官能性ブロックコポリマ |
| GB2521655A (en) * | 2013-12-27 | 2015-07-01 | Nipsea Technologies Pte Ltd | Water dispersible dendritic polymers |
| CA2956431C (en) | 2014-07-03 | 2023-01-31 | ATRP Solutions, Inc. | Surfactant-compatible star macromolecules |
| US10618998B2 (en) * | 2014-11-12 | 2020-04-14 | Purdue Research Foundation | Poly(alkylene carbonate)-based amphiphilic block copolymers and methods of use thereof |
| WO2016123107A1 (en) * | 2015-01-28 | 2016-08-04 | The Administrators Of The Tulane Educational Fund | Nanoparticle polymer grafted dispersants and unimolecular micelles and methods of use |
| CN104998550B (zh) * | 2015-06-30 | 2017-10-10 | 天津大学 | 填充具有交联疏水段的两亲性表面改性材料的抗污染超滤膜及制备方法 |
| CN108078926B (zh) * | 2017-12-20 | 2020-07-07 | 临沂大学 | 一种肿瘤主动靶向星形两亲聚合物胶束纳米药物及其制备方法 |
| GB201815523D0 (en) * | 2018-09-24 | 2018-11-07 | Imperial Innovations Ltd | Polymers |
| WO2021158496A1 (en) | 2020-02-07 | 2021-08-12 | Medtronic, Inc. | Drug formulations for reservoir-based delivery |
| WO2021167786A1 (en) * | 2020-02-20 | 2021-08-26 | Medtronic, Inc. | Drug infusion devices compatible with drug formulations |
| CN116323893A (zh) | 2020-10-16 | 2023-06-23 | 宝洁公司 | 包含包封物群体的消费产品组合物 |
| US12227720B2 (en) | 2020-10-16 | 2025-02-18 | The Procter & Gamble Company | Consumer product compositions with at least two encapsulate populations |
| US12486478B2 (en) | 2020-10-16 | 2025-12-02 | The Procter & Gamble Company | Consumer products comprising delivery particles with high core:wall ratios |
| CN114735943B (zh) * | 2022-04-12 | 2023-09-26 | 江苏大学 | 聚（3-环己基丙酸烯丙酯）纳米刷的制备方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3924896C1 (https=) | 1989-07-27 | 1990-09-27 | Blaupunkt-Werke Gmbh, 3200 Hildesheim, De | |
| US5371147A (en) * | 1990-10-11 | 1994-12-06 | Permeable Technologies, Inc. | Silicone-containing acrylic star polymers, block copolymers and macromonomers |
| JP3753328B2 (ja) * | 1990-10-11 | 2006-03-08 | パーミアブル・テクノロジーズ・インク | 新規なシリコーン含有ポリマー及び前記ポリマーからの酸素透過性親水性コンタクトレンズ |
| DE4139962A1 (de) * | 1991-12-04 | 1993-06-09 | Basf Ag, 6700 Ludwigshafen, De | Blockcopolymere aus acrylat- und methacrylateinheiten |
| US5763548A (en) * | 1995-03-31 | 1998-06-09 | Carnegie-Mellon University | (Co)polymers and a novel polymerization process based on atom (or group) transfer radical polymerization |
| DE19524045A1 (de) | 1995-07-01 | 1997-01-02 | Basf Ag | Hochfunktionalisierte Polyurethane |
| US5807937A (en) * | 1995-11-15 | 1998-09-15 | Carnegie Mellon University | Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties |
| JPH10204022A (ja) * | 1997-01-23 | 1998-08-04 | T Hasegawa Co Ltd | ３−シクロヘキシルプロピオン酸の製造法 |
| FR2759582A1 (fr) | 1997-02-14 | 1998-08-21 | Oreal | Composition deodorante |
| FR2790405B1 (fr) * | 1999-03-02 | 2001-04-20 | Oreal | Nanocapsules a base de polymeres dendritiques |
| FR2791989A1 (fr) | 1999-04-06 | 2000-10-13 | Oreal | Composition notamment cosmetique comprenant des polymeres ayant une structure en etoiles, lesdits polymeres et leur utilisation |
| FR2791987A1 (fr) * | 1999-04-06 | 2000-10-13 | Oreal | Composition notamment cosmetique comprenant des polymeres ayant une structure en etoiles, lesdits polymeres et leur utilisation |
| US6569956B1 (en) | 1999-12-22 | 2003-05-27 | Basf Corporation | Hyperbranched polyol macromolecule, method of making same, and coating composition including same |
| US20040009229A1 (en) * | 2000-01-05 | 2004-01-15 | Unger Evan Charles | Stabilized nanoparticle formulations of camptotheca derivatives |
| CA2398575A1 (en) | 2000-02-09 | 2001-08-16 | Ciba Specialty Chemicals Holding Inc. | Hyperbranched amphiphilic polymeric additives and polymer compositions with increased surface energy |
| US7097856B2 (en) * | 2000-09-29 | 2006-08-29 | The Regents Of The University Of California | Dendrimeric support or carrier macromolecule |
| US20020115798A1 (en) * | 2000-12-20 | 2002-08-22 | Sridevi Narayan-Sarathy | Star-branched anionic polymers |
| TWI246524B (en) * | 2001-01-19 | 2006-01-01 | Shearwater Corp | Multi-arm block copolymers as drug delivery vehicles |
| JP2002265613A (ja) * | 2001-03-07 | 2002-09-18 | Kawamura Inst Of Chem Res | ポルフィリンを含有する星型高分子のミセル |
| US7063895B2 (en) * | 2001-08-01 | 2006-06-20 | National Starch And Chemical Investment Holding Corporation | Hydrophobically modified solution polymers and their use in surface protecting formulations |
| AU2002365296A1 (en) * | 2001-11-29 | 2003-06-10 | L'oreal | Adhesive block ethylene copolymers, cosmetic compositions containing same, and use thereof in cosmetics |
| MXPA04005512A (es) * | 2001-12-13 | 2004-12-06 | Firmenich & Cie | Compuestos para liberacion controlada de moleculas activas. |
| US6930151B2 (en) * | 2002-04-04 | 2005-08-16 | University Of Akron | Star block copolymers comprising polyisobutylene-B-polyacrylonitrile arms radiating from an aromatic core |
| MXPA05001005A (es) * | 2002-07-26 | 2005-05-16 | Atofina | Composicion adhesiva para un medio humedo, con base en copolimeros de bloqueo que comprenden por lo menos un bloque hidrofilo. |
| EP1433799A3 (en) * | 2002-12-23 | 2004-07-14 | Ucb, S.A. | Star shaped acrylic block copolymer |
| ATE461961T1 (de) * | 2002-12-30 | 2010-04-15 | Nektar Therapeutics | Mehrarmige polypeptid-poly(ethylenglykol)- blockcopolymere als arzneistoffzufuhrvehikel |
| EP1443058A1 (en) | 2003-01-29 | 2004-08-04 | Firmenich Sa | Polymeric particles and fragrance delivery systems |
-
2005
- 2005-10-10 EP EP05791696A patent/EP1814924A2/en not_active Withdrawn
- 2005-10-10 WO PCT/IB2005/003023 patent/WO2006038110A2/en not_active Ceased
- 2005-10-10 CN CN2005800337635A patent/CN101035823B/zh not_active Expired - Fee Related
- 2005-10-10 MX MX2007004048A patent/MX301374B/es active IP Right Grant
- 2005-10-10 RU RU2007117150/04A patent/RU2007117150A/ru not_active Application Discontinuation
- 2005-10-10 BR BRPI0516259-9A patent/BRPI0516259A/pt not_active IP Right Cessation
- 2005-10-10 JP JP2007535267A patent/JP5090915B2/ja not_active Expired - Fee Related
-
2007
- 2007-03-22 US US11/690,074 patent/US20070160561A1/en not_active Abandoned
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