KR20010043187A - 농업용으로 유용한 생활성 제제를 위한 전달 매개체로서의미소구체 - Google Patents
농업용으로 유용한 생활성 제제를 위한 전달 매개체로서의미소구체 Download PDFInfo
- Publication number
- KR20010043187A KR20010043187A KR1020007012110A KR20007012110A KR20010043187A KR 20010043187 A KR20010043187 A KR 20010043187A KR 1020007012110 A KR1020007012110 A KR 1020007012110A KR 20007012110 A KR20007012110 A KR 20007012110A KR 20010043187 A KR20010043187 A KR 20010043187A
- Authority
- KR
- South Korea
- Prior art keywords
- microspheres
- elastic
- microsphere
- active agent
- loaded
- 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.)
- Withdrawn
Links
- 239000004005 microsphere Substances 0.000 title claims abstract description 163
- 239000012867 bioactive agent Substances 0.000 title 1
- 239000003981 vehicle Substances 0.000 title 1
- 239000013543 active substance Substances 0.000 claims abstract description 79
- 238000000034 method Methods 0.000 claims abstract description 48
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 21
- 230000003287 optical effect Effects 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 62
- 239000000178 monomer Substances 0.000 claims description 47
- 239000002245 particle Substances 0.000 claims description 30
- 239000008346 aqueous phase Substances 0.000 claims description 22
- 239000003999 initiator Substances 0.000 claims description 20
- 239000003016 pheromone Substances 0.000 claims description 20
- 239000012071 phase Substances 0.000 claims description 18
- 239000004094 surface-active agent Substances 0.000 claims description 18
- 238000010557 suspension polymerization reaction Methods 0.000 claims description 15
- 229920001567 vinyl ester resin Polymers 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 13
- 150000003254 radicals Chemical class 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 239000003381 stabilizer Substances 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 239000002917 insecticide Substances 0.000 claims description 7
- 239000004009 herbicide Substances 0.000 claims description 5
- 239000000417 fungicide Substances 0.000 claims description 4
- 230000000977 initiatory effect Effects 0.000 claims description 3
- 239000000077 insect repellent Substances 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- 230000000855 fungicidal effect Effects 0.000 claims 2
- 230000002363 herbicidal effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 239000007787 solid Substances 0.000 description 30
- 239000006185 dispersion Substances 0.000 description 29
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 15
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- 238000010348 incorporation Methods 0.000 description 14
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 229940048053 acrylate Drugs 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- DSCFFEYYQKSRSV-UHFFFAOYSA-N 1L-O1-methyl-muco-inositol Natural products COC1C(O)C(O)C(O)C(O)C1O DSCFFEYYQKSRSV-UHFFFAOYSA-N 0.000 description 11
- 239000004342 Benzoyl peroxide Substances 0.000 description 11
- 235000019400 benzoyl peroxide Nutrition 0.000 description 11
- 239000008367 deionised water Substances 0.000 description 11
- 229910021641 deionized water Inorganic materials 0.000 description 11
- 241000238631 Hexapoda Species 0.000 description 10
- YGHAIPJLMYTNAI-ONEGZZNKSA-N 11E-Tetradecen-1-ol Chemical compound CC\C=C\CCCCCCCCCCO YGHAIPJLMYTNAI-ONEGZZNKSA-N 0.000 description 9
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 9
- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 206010037660 Pyrexia Diseases 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 239000003431 cross linking reagent Substances 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000004971 Cross linker Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- -1 metrizin Chemical compound 0.000 description 5
- 238000000386 microscopy Methods 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000012798 spherical particle Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- JRJDUARFFRHJHP-BJILWQEISA-N acetic acid;(e)-tetradec-11-enal Chemical compound CC(O)=O.CC\C=C\CCCCCCCCCC=O JRJDUARFFRHJHP-BJILWQEISA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 239000011149 active material Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 description 4
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000012695 Interfacial polymerization Methods 0.000 description 3
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- WPKYZIPODULRBM-UHFFFAOYSA-N azane;prop-2-enoic acid Chemical compound N.OC(=O)C=C WPKYZIPODULRBM-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- CMDXMIHZUJPRHG-UHFFFAOYSA-N ethenyl decanoate Chemical compound CCCCCCCCCC(=O)OC=C CMDXMIHZUJPRHG-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 238000000399 optical microscopy Methods 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 2
- LMAUULKNZLEMGN-UHFFFAOYSA-N 1-ethyl-3,5-dimethylbenzene Chemical compound CCC1=CC(C)=CC(C)=C1 LMAUULKNZLEMGN-UHFFFAOYSA-N 0.000 description 2
- ZVYGIPWYVVJFRW-UHFFFAOYSA-N 3-methylbutyl prop-2-enoate Chemical compound CC(C)CCOC(=O)C=C ZVYGIPWYVVJFRW-UHFFFAOYSA-N 0.000 description 2
- CUXGDKOCSSIRKK-UHFFFAOYSA-N 7-methyloctyl prop-2-enoate Chemical compound CC(C)CCCCCCOC(=O)C=C CUXGDKOCSSIRKK-UHFFFAOYSA-N 0.000 description 2
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- 244000166675 Cymbopogon nardus Species 0.000 description 2
- 235000018791 Cymbopogon nardus Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- GILDFPGOCAQXOP-UHFFFAOYSA-N azanium;2-methylprop-2-enimidate Chemical compound N.CC(=C)C(N)=O GILDFPGOCAQXOP-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229930003633 citronellal Natural products 0.000 description 2
- 235000000983 citronellal Nutrition 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- IGBZOHMCHDADGY-UHFFFAOYSA-N ethenyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC=C IGBZOHMCHDADGY-UHFFFAOYSA-N 0.000 description 2
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920003251 poly(α-methylstyrene) Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229940047670 sodium acrylate Drugs 0.000 description 2
- 238000000935 solvent evaporation Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000010558 suspension polymerization method Methods 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 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
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229920003176 water-insoluble polymer Polymers 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical class C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical class C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical class C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- FLCRHJKOKJPOQG-UHFFFAOYSA-N 2-methoxyethyl(dimethyl)azanium;propanoate Chemical compound CCC([O-])=O.COCC[NH+](C)C FLCRHJKOKJPOQG-UHFFFAOYSA-N 0.000 description 1
- NCTBYWFEJFTVEL-UHFFFAOYSA-N 2-methylbutyl prop-2-enoate Chemical compound CCC(C)COC(=O)C=C NCTBYWFEJFTVEL-UHFFFAOYSA-N 0.000 description 1
- ZAWQXWZJKKICSZ-UHFFFAOYSA-N 3,3-dimethyl-2-methylidenebutanamide Chemical compound CC(C)(C)C(=C)C(N)=O ZAWQXWZJKKICSZ-UHFFFAOYSA-N 0.000 description 1
- BVDBXCXQMHBGQM-UHFFFAOYSA-N 4-methylpentan-2-yl prop-2-enoate Chemical compound CC(C)CC(C)OC(=O)C=C BVDBXCXQMHBGQM-UHFFFAOYSA-N 0.000 description 1
- IUNVCWLKOOCPIT-UHFFFAOYSA-N 6-methylheptylsulfanyl 2-hydroxyacetate Chemical compound CC(C)CCCCCSOC(=O)CO IUNVCWLKOOCPIT-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- ZFQMGOCRWDJUCX-HJWRWDBZSA-N 7Z-Tetradecen-2-one Chemical compound CCCCCC\C=C/CCCCC(C)=O ZFQMGOCRWDJUCX-HJWRWDBZSA-N 0.000 description 1
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 241000255942 Choristoneura fumiferana Species 0.000 description 1
- 241001525906 Choristoneura parallela Species 0.000 description 1
- 241001124562 Choristoneura rosaceana Species 0.000 description 1
- 241001635274 Cydia pomonella Species 0.000 description 1
- 241001300247 Dendroctonus frontalis Species 0.000 description 1
- 239000004593 Epoxy Chemical class 0.000 description 1
- ZFMSMUAANRJZFM-UHFFFAOYSA-N Estragole Chemical compound COC1=CC=C(CC=C)C=C1 ZFMSMUAANRJZFM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 241000060469 Eupoecilia ambiguella Species 0.000 description 1
- 241000801160 Euura alaskensis Species 0.000 description 1
- 241000519875 Exomala orientalis Species 0.000 description 1
- 241001441330 Grapholita molesta Species 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 241000400431 Keiferia lycopersicella Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- 241000721451 Pectinophora gossypiella Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000005025 cast polypropylene Substances 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 229920003020 cross-linked polyethylene Polymers 0.000 description 1
- 239000004703 cross-linked polyethylene Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 229940124447 delivery agent Drugs 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000012674 dispersion polymerization Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- LZWYWAIOTBEZFN-UHFFFAOYSA-N ethenyl hexanoate Chemical compound CCCCCC(=O)OC=C LZWYWAIOTBEZFN-UHFFFAOYSA-N 0.000 description 1
- QBDADGJLZNIRFQ-UHFFFAOYSA-N ethenyl octanoate Chemical compound CCCCCCCC(=O)OC=C QBDADGJLZNIRFQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000003673 groundwater Substances 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 244000144972 livestock Species 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
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- RCLLINSDAJVOHP-UHFFFAOYSA-N n-ethyl-n',n'-dimethylprop-2-enehydrazide Chemical compound CCN(N(C)C)C(=O)C=C RCLLINSDAJVOHP-UHFFFAOYSA-N 0.000 description 1
- AWGZKFQMWZYCHF-UHFFFAOYSA-N n-octylprop-2-enamide Chemical compound CCCCCCCCNC(=O)C=C AWGZKFQMWZYCHF-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000005026 oriented polypropylene Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
- XZHNPVKXBNDGJD-UHFFFAOYSA-N tetradecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C=C XZHNPVKXBNDGJD-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
- A01N25/28—Microcapsules or nanocapsules
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/071,567 | 1998-05-01 | ||
| US09/071,567 US6471975B1 (en) | 1998-05-01 | 1998-05-01 | Microspheres as a delivery vehicle for bio-active agents useful in agricultural applications |
| PCT/US1999/006064 WO1999056541A1 (en) | 1998-05-01 | 1999-03-19 | Microspheres as a delivery vehicle for bio-active agents useful in agricultural applications |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20010043187A true KR20010043187A (ko) | 2001-05-25 |
Family
ID=22102160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020007012110A Withdrawn KR20010043187A (ko) | 1998-05-01 | 1999-03-19 | 농업용으로 유용한 생활성 제제를 위한 전달 매개체로서의미소구체 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6471975B1 (enExample) |
| EP (1) | EP1075182B1 (enExample) |
| JP (1) | JP4473447B2 (enExample) |
| KR (1) | KR20010043187A (enExample) |
| AU (1) | AU3011799A (enExample) |
| BR (1) | BR9910181A (enExample) |
| CA (1) | CA2330852C (enExample) |
| DE (1) | DE69905243T2 (enExample) |
| WO (1) | WO1999056541A1 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7354596B1 (en) * | 1998-05-01 | 2008-04-08 | 3M Innovative Properties Company | Anti-microbial agent delivery system |
| US6540991B2 (en) | 2001-04-06 | 2003-04-01 | 3M Innovative Properties Company | Stabilized active materials |
| US6644405B2 (en) * | 2002-03-21 | 2003-11-11 | Halliburton Energy Services, Inc. | Storable water-microsphere suspensions for use in well cements and methods |
| US20030181542A1 (en) * | 2002-03-21 | 2003-09-25 | Vijn Jan Pieter | Storable water-silica suspensions and methods |
| US6838576B1 (en) | 2003-10-23 | 2005-01-04 | 3M Innovative Properties Company | Process for preparing functional group-containing olefinic compounds |
| US6983800B2 (en) * | 2003-10-29 | 2006-01-10 | Halliburton Energy Services, Inc. | Methods, cement compositions and oil suspensions of powder |
| US7156174B2 (en) | 2004-01-30 | 2007-01-02 | Halliburton Energy Services, Inc. | Contained micro-particles for use in well bore operations |
| US7341104B2 (en) * | 2004-02-10 | 2008-03-11 | Halliburton Energy Services, Inc. | Methods of using substantially hydrated cement particulates in subterranean applications |
| US7086466B2 (en) * | 2004-02-10 | 2006-08-08 | Halliburton Energy Services, Inc. | Use of substantially hydrated cement particulates in drilling and subterranean applications |
| US9512346B2 (en) * | 2004-02-10 | 2016-12-06 | Halliburton Energy Services, Inc. | Cement compositions and methods utilizing nano-hydraulic cement |
| US8183186B2 (en) | 2004-02-10 | 2012-05-22 | Halliburton Energy Services, Inc. | Cement-based particulates and methods of use |
| US20060166834A1 (en) * | 2004-02-10 | 2006-07-27 | Halliburton Energy Services, Inc. | Subterranean treatment fluids comprising substantially hydrated cement particulates |
| US7939578B2 (en) * | 2007-02-23 | 2011-05-10 | 3M Innovative Properties Company | Polymeric fibers and methods of making |
| US8476203B2 (en) | 2007-05-10 | 2013-07-02 | Halliburton Energy Services, Inc. | Cement compositions comprising sub-micron alumina and associated methods |
| US9206344B2 (en) | 2007-05-10 | 2015-12-08 | Halliburton Energy Services, Inc. | Sealant compositions and methods utilizing nano-particles |
| US8586512B2 (en) | 2007-05-10 | 2013-11-19 | Halliburton Energy Services, Inc. | Cement compositions and methods utilizing nano-clay |
| US9199879B2 (en) | 2007-05-10 | 2015-12-01 | Halliburton Energy Serives, Inc. | Well treatment compositions and methods utilizing nano-particles |
| US9512351B2 (en) | 2007-05-10 | 2016-12-06 | Halliburton Energy Services, Inc. | Well treatment fluids and methods utilizing nano-particles |
| US8685903B2 (en) | 2007-05-10 | 2014-04-01 | Halliburton Energy Services, Inc. | Lost circulation compositions and associated methods |
| US8513322B2 (en) * | 2007-05-31 | 2013-08-20 | 3M Innovative Properties Company | Polymeric beads and methods of making polymeric beads |
| BRPI0820704A2 (pt) * | 2007-12-12 | 2015-06-16 | 3M Innovative Proferties Company | Métodos de fabricação de materiais poliméricos moldados |
| WO2011030824A1 (ja) * | 2009-09-11 | 2011-03-17 | 日本エンバイロケミカルズ株式会社 | 徐放性粒子およびその製造方法 |
| JP6083936B2 (ja) | 2011-03-11 | 2017-02-22 | 大阪ガスケミカル株式会社 | 徐放性粒子の製造方法 |
| JP5763570B2 (ja) * | 2011-03-11 | 2015-08-12 | 大阪ガスケミカル株式会社 | 徐放性粒子およびその製造方法 |
| US10322301B2 (en) | 2012-11-06 | 2019-06-18 | CoLabs International Corporation | Compositions containing a cellulose derived capsule with a sunscreen active agent |
| EP2916814B1 (en) | 2012-11-06 | 2020-02-12 | Colabs International Corporation | Composition containing a cellulose derived capsule with a sunscreen |
| US11690793B2 (en) | 2012-11-06 | 2023-07-04 | Colabs Int'l Corp. | Composition containing a cellulose derived capsule with a sunscreen |
| US11724134B2 (en) | 2012-11-06 | 2023-08-15 | CoLabs International Corporation | Compositions containing a cellulose derived capsule with a sunscreen active agent |
| US11491088B2 (en) | 2012-11-06 | 2022-11-08 | CoLabs International Corporation | Compositions containing a capsule with a moisturizing agent |
| US11707421B2 (en) | 2012-11-06 | 2023-07-25 | Colabs Int'l Corp. | Compositions containing a flexible derived capsule with an active agent |
| WO2015030213A1 (ja) * | 2013-08-30 | 2015-03-05 | 日本エンバイロケミカルズ株式会社 | 徐放性粒子、その製造方法、成形材料および成形品 |
| FR3032600B1 (fr) | 2015-02-18 | 2020-04-03 | Melchior Material And Life Science France | Particules contenant des pheromones et procede de fabrication |
| WO2018148614A1 (en) * | 2017-02-10 | 2018-08-16 | CoLabs International Corporation | Compositions containing a flexible capsule with an active agent |
| CN107296046B (zh) * | 2017-03-20 | 2020-01-07 | 浙江工商大学 | 一种2-氨基苯并咪唑杀菌微球及其合成方法和应用 |
| EP3813786A4 (en) | 2018-06-27 | 2022-06-29 | Colabs International Corporation | Compositions comprising silicon dioxide-based particles including one or more agents |
| FR3107667A1 (fr) | 2020-02-27 | 2021-09-03 | Melchior Material And Life Science France | Doses unitaires pour la liberation d’une formulation aqueuse |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US505436A (en) * | 1893-09-26 | Fly-frame | ||
| US3691140A (en) | 1970-03-09 | 1972-09-12 | Spencer Ferguson Silver | Acrylate copolymer microspheres |
| US3928546A (en) | 1970-12-11 | 1975-12-23 | Thiokol Corp | Method and apparatus for making ammonium perchlorate |
| US3928564A (en) * | 1971-11-01 | 1975-12-23 | Goodrich Co B F | Biocidal elastomeric composition combinations and method for dispersing biocides therewith |
| US4166152B1 (en) | 1977-08-17 | 1999-05-18 | Minnesota Mining & Mfg | Tacky polymeric microspheres |
| DE2805106A1 (de) * | 1978-02-07 | 1979-08-16 | Hoechst Ag | Mikrokapseln aus polyvinylalkohol mit fluessigem, wasserunloeslichem fuellgut und verfahren zu deren herstellung |
| WO1981002505A1 (en) | 1980-03-05 | 1981-09-17 | Ici Ltd | Stabilised compositions containing behaviour modifying compounds |
| US4353962A (en) | 1980-05-15 | 1982-10-12 | Environmental Chemicals, Inc. | In-flight encapsulation of particles |
| US4415615A (en) | 1982-01-15 | 1983-11-15 | Minnesota Mining And Manufacturing Co. | Cellular pressure-sensitive adhesive product and method of making |
| US4495318A (en) | 1984-03-21 | 1985-01-22 | International Cube Corporation | Low tack microsphere glue |
| US4707355A (en) * | 1985-01-22 | 1987-11-17 | The Dow Chemical Company | Microencapsulated insecticidal bait formulations as fumigants |
| US4690825A (en) | 1985-10-04 | 1987-09-01 | Advanced Polymer Systems, Inc. | Method for delivering an active ingredient by controlled time release utilizing a novel delivery vehicle which can be prepared by a process utilizing the active ingredient as a porogen |
| CA1302242C (en) | 1985-12-09 | 1992-06-02 | Tanabe Seiyaku Co., Ltd. | Rodent-repellent microcapsules and preparations thereof |
| US4786696A (en) | 1987-02-06 | 1988-11-22 | Minnesota Mining And Manufacturing Company | Process for the preparation of tacky polymeric microspheres |
| US5460817A (en) * | 1988-01-19 | 1995-10-24 | Allied Colloids Ltd. | Particulate composition comprising a core of matrix polymer with active ingredient distributed therein |
| US4988467A (en) | 1988-02-26 | 1991-01-29 | W. R. Grace & Co.-Conn. | Method of forming hot melt gaskets |
| US5053436A (en) | 1988-11-30 | 1991-10-01 | Minnesota Mining And Manufacturing Company | Hollow acrylate polymer microspheres |
| US5045569A (en) | 1988-11-30 | 1991-09-03 | Minnesota Mining And Manufacturing Company | Hollow acrylate polymer microspheres |
| US4994322A (en) | 1989-09-18 | 1991-02-19 | Minnesota Mining And Manufacturing | Pressure-sensitive adhesive comprising hollow tacky microspheres and macromonomer-containing binder copolymer |
| US4968562A (en) | 1990-02-27 | 1990-11-06 | Minnesota Mining And Manufacturing Company | Hollow acid-free acrylate polymeric microspheres having multiple small voids |
| US5215818A (en) | 1990-04-20 | 1993-06-01 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesive comprising solid tacky microspheres and macromonomer-containing binder copolymer |
| US5118750A (en) | 1990-04-20 | 1992-06-02 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesive comprising solid tacky microspheres and macromonomer-containing binder copolymer |
| US5120349A (en) | 1990-12-07 | 1992-06-09 | Landec Labs, Inc. | Microcapsule having temperature-dependent permeability profile |
| US5503839A (en) | 1991-10-16 | 1996-04-02 | Shin-Etsu Chemical Co., Ltd. | Method for the preparation of a sustained-release dispenser of sex pheromone of pest insects |
| US5286493A (en) | 1992-01-27 | 1994-02-15 | Euroceltique, S.A. | Stabilized controlled release formulations having acrylic polymer coating |
| US5580578A (en) | 1992-01-27 | 1996-12-03 | Euro-Celtique, S.A. | Controlled release formulations coated with aqueous dispersions of acrylic polymers |
| EP0595030A3 (en) | 1992-10-01 | 1995-06-07 | Tanabe Seiyaku Co | Multi-core microspheres with delayed drug delivery and process for their manufacture. |
| TW338043B (en) | 1992-12-11 | 1998-08-11 | Minnesota Mining & Mfg | Tacky microspheres having pendant hydrophilic polymeric or oligomeric moieties |
| US5571617A (en) | 1993-04-23 | 1996-11-05 | Minnesota Mining And Manufacturing Company | Pressure sensitive adhesive comprising tacky surface active microspheres |
| PL186226B1 (pl) | 1993-11-15 | 2003-12-31 | Zeneca Ltd | Mikrokapsułka i sposób wytwarzania mikrokapsułek zawierających stały środek agrochemiczny zawieszony w cieczy organicznej nie mieszającej się z wodą |
| US5639710A (en) | 1994-07-06 | 1997-06-17 | Zeneca Limited | Solid microspheres for agriculturally active compounds and process for their production |
| WO1996001280A1 (en) | 1994-07-01 | 1996-01-18 | Minnesota Mining And Manufacturing Company | Tacky microspheres prepared from vinyl ester monomers |
| US5824748A (en) | 1996-06-03 | 1998-10-20 | Minnesota Mining And Manufacturing Company | Composite pressure sensitive adhesive microspheres |
| US5889118A (en) | 1996-06-03 | 1999-03-30 | Minnesota Mining And Manufacturing Company | Thermomorphic "smart" pressure sensitive adhesives |
| US6526906B1 (en) | 1996-10-18 | 2003-03-04 | Edward Bidanset | Page marking device |
| US6080418A (en) | 1997-04-07 | 2000-06-27 | 3M Innovative Properties Company | Suspensions of microcapsules containing biologically active ingredients and adhesive microspheres |
-
1998
- 1998-05-01 US US09/071,567 patent/US6471975B1/en not_active Expired - Lifetime
-
1999
- 1999-03-19 CA CA002330852A patent/CA2330852C/en not_active Expired - Fee Related
- 1999-03-19 BR BR9910181-5A patent/BR9910181A/pt not_active Application Discontinuation
- 1999-03-19 JP JP2000546587A patent/JP4473447B2/ja not_active Expired - Fee Related
- 1999-03-19 EP EP99911481A patent/EP1075182B1/en not_active Expired - Lifetime
- 1999-03-19 WO PCT/US1999/006064 patent/WO1999056541A1/en not_active Ceased
- 1999-03-19 DE DE69905243T patent/DE69905243T2/de not_active Expired - Lifetime
- 1999-03-19 KR KR1020007012110A patent/KR20010043187A/ko not_active Withdrawn
- 1999-03-19 AU AU30117/99A patent/AU3011799A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2330852A1 (en) | 1999-11-11 |
| CA2330852C (en) | 2008-09-02 |
| AU3011799A (en) | 1999-11-23 |
| JP2002513038A (ja) | 2002-05-08 |
| DE69905243T2 (de) | 2003-12-11 |
| WO1999056541A1 (en) | 1999-11-11 |
| DE69905243D1 (de) | 2003-03-13 |
| US6471975B1 (en) | 2002-10-29 |
| JP4473447B2 (ja) | 2010-06-02 |
| EP1075182B1 (en) | 2003-02-05 |
| BR9910181A (pt) | 2001-01-09 |
| EP1075182A1 (en) | 2001-02-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20010043187A (ko) | 농업용으로 유용한 생활성 제제를 위한 전달 매개체로서의미소구체 | |
| EP1221840B1 (en) | Active material within hydrogel microbeads | |
| US6375968B1 (en) | Encapsulated active material immobilized in hydrogel microbeads | |
| AU744180B2 (en) | Adherent microcapsules containing biologically active ingredients | |
| CA1162478A (en) | Stable insecticide containing latexes, method of making and method of distributing insecticide | |
| JP4663830B2 (ja) | 有害生物防除剤組成物 | |
| WO2002089576A1 (en) | Active material immobilized in stable hydrogel microbeads | |
| CA2378269A1 (en) | Composition containing an active substance, production and use thereof | |
| JPH02500598A (ja) | ポリマー組成物 | |
| MX2007000164A (es) | Un sistema de entrega seguro para materiales agricolamente activos. | |
| JP2004525947A (ja) | 安定化された活性物質 | |
| CA1250229A (en) | Pest control | |
| US7951390B2 (en) | Slow-release microcapsule composition for safe delivery of agriculturally active material | |
| JP4615662B2 (ja) | 被覆用組成物 | |
| AU2001272464B2 (en) | Stabilisation of light sensitive substances | |
| US7786194B2 (en) | Compositions and methods for protecting materials from damage | |
| KR20230119127A (ko) | 마이크로캡슐의 제조 방법 | |
| JPH04352703A (ja) | Ｐ−メンタン誘導体を含有する害虫忌避マイクロカプセル剤 | |
| AU618553B2 (en) | Polymeric compositions | |
| JPH0331201A (ja) | 農薬製剤組成物 | |
| MXPA99009066A (en) | Adherent microcapsules containing biologically active ingredients |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20001031 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |