EP2352580A1 - Verfahren zur herstellung von effektstoff-haltigen mikropartikeln - Google Patents
Verfahren zur herstellung von effektstoff-haltigen mikropartikelnInfo
- Publication number
- EP2352580A1 EP2352580A1 EP09821620A EP09821620A EP2352580A1 EP 2352580 A1 EP2352580 A1 EP 2352580A1 EP 09821620 A EP09821620 A EP 09821620A EP 09821620 A EP09821620 A EP 09821620A EP 2352580 A1 EP2352580 A1 EP 2352580A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- microparticles
- monomers
- acid
- polyisocyanates
- ethylenically unsaturated
- 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- Withdrawn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
- 239000011859 microparticle Substances 0.000 title claims abstract description 92
- 230000000694 effects Effects 0.000 title claims abstract description 60
- 239000000126 substance Substances 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 55
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- 239000000178 monomer Substances 0.000 claims abstract description 123
- 239000000203 mixture Substances 0.000 claims abstract description 53
- 229920000728 polyester Polymers 0.000 claims abstract description 52
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 35
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 35
- 102000004190 Enzymes Human genes 0.000 claims abstract description 30
- 108090000790 Enzymes Proteins 0.000 claims abstract description 30
- 239000000725 suspension Substances 0.000 claims abstract description 25
- 229920000642 polymer Polymers 0.000 claims abstract description 20
- 239000003905 agrochemical Substances 0.000 claims abstract description 17
- 238000009472 formulation Methods 0.000 claims abstract description 17
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 14
- 239000003337 fertilizer Substances 0.000 claims abstract description 13
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 13
- 241000238631 Hexapoda Species 0.000 claims abstract description 12
- 239000003139 biocide Substances 0.000 claims abstract description 11
- 239000000575 pesticide Substances 0.000 claims abstract description 10
- 239000002537 cosmetic Substances 0.000 claims abstract description 9
- 241000233866 Fungi Species 0.000 claims abstract description 8
- 235000013305 food Nutrition 0.000 claims abstract description 8
- 239000000123 paper Substances 0.000 claims abstract description 8
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- 238000003786 synthesis reaction Methods 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 6
- 239000010985 leather Substances 0.000 claims abstract description 6
- 239000004753 textile Substances 0.000 claims abstract description 6
- 239000003599 detergent Substances 0.000 claims abstract description 5
- 201000002266 mite infestation Diseases 0.000 claims abstract description 4
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 4
- 230000008635 plant growth Effects 0.000 claims abstract description 4
- -1 Pharmakum Substances 0.000 claims description 93
- 238000006116 polymerization reaction Methods 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 14
- 229920000768 polyamine Polymers 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 11
- 239000011814 protection agent Substances 0.000 claims description 11
- 229920005862 polyol Polymers 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 239000003086 colorant Substances 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
- 206010061217 Infestation Diseases 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims description 2
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- 238000005406 washing Methods 0.000 claims description 2
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- 235000013373 food additive Nutrition 0.000 claims 1
- 150000001261 hydroxy acids Chemical class 0.000 claims 1
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- 241001465754 Metazoa Species 0.000 abstract description 6
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- 239000012752 auxiliary agent Substances 0.000 abstract 1
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- 239000002775 capsule Substances 0.000 description 39
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- 239000012071 phase Substances 0.000 description 32
- 239000002270 dispersing agent Substances 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 23
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 22
- 239000003995 emulsifying agent Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000011162 core material Substances 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 16
- 239000011257 shell material Substances 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 235000002639 sodium chloride Nutrition 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 12
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 11
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000003158 alcohol group Chemical group 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000002480 mineral oil Substances 0.000 description 10
- 235000010446 mineral oil Nutrition 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 10
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 238000007046 ethoxylation reaction Methods 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000000084 colloidal system Substances 0.000 description 8
- 239000000417 fungicide Substances 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 7
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 7
- 102000004157 Hydrolases Human genes 0.000 description 7
- 108090000604 Hydrolases Proteins 0.000 description 7
- 239000005859 Triticonazole Substances 0.000 description 7
- 125000000129 anionic group Chemical group 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- 150000002596 lactones Chemical class 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- 238000001878 scanning electron micrograph Methods 0.000 description 7
- 229960002920 sorbitol Drugs 0.000 description 7
- 238000002604 ultrasonography Methods 0.000 description 7
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 150000002191 fatty alcohols Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 5
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 5
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 5
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 5
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 description 5
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000012975 dibutyltin dilaurate Substances 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000004009 herbicide Substances 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000002685 polymerization catalyst Substances 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 108090001060 Lipase Proteins 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000003851 azoles Chemical class 0.000 description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
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- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
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- 230000035515 penetration Effects 0.000 description 4
- 238000000053 physical method Methods 0.000 description 4
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- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 239000004215 Carbon black (E152) Substances 0.000 description 3
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- 239000004367 Lipase Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000005868 Metconazole Substances 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
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- 239000004435 Oxo alcohol Substances 0.000 description 3
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- 230000005855 radiation Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 3
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 3
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 3
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 2
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- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- ZOKXUAHZSKEQSS-UHFFFAOYSA-N tribufos Chemical compound CCCCSP(=O)(SCCCC)SCCCC ZOKXUAHZSKEQSS-UHFFFAOYSA-N 0.000 description 1
- WVZPYZMQQDNINJ-UHFFFAOYSA-N tributyl(butylstannyloxy)stannane Chemical compound CCCC[SnH](CCCC)O[SnH](CCCC)CCCC WVZPYZMQQDNINJ-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- PGAANEHXBMZPPR-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O.OC(=O)CCCCCCCCCCCC(O)=O PGAANEHXBMZPPR-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- WMRNPTXYRLMGPC-UHFFFAOYSA-L trimethyl(octyl)azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCCCCCC[N+](C)(C)C.CCCCCCCC[N+](C)(C)C WMRNPTXYRLMGPC-UHFFFAOYSA-L 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
Definitions
- the present invention is a process for the preparation of effect-containing microparticles M comprising A) the formation of a crude suspension of microparticles A by enzymatic polyester synthesis in an inverse miniemulsion containing enzyme, effect material and polyester monomers; and B) the polymerization of wall monomers from the group of ethylenically unsaturated monomers, polyisocyanates and / or polyepoxides in the crude suspension of microparticles A.
- the present invention further relates to microparticles M obtainable by the process according to the invention and an agrochemical formulation
- the present invention relates to the use of microparticles M prepared according to the invention as a component in colorants, cosmetics, pharmaceuticals, biocide, crop protection agents, fertilizers, additives for food or animal feed, auxiliaries for polymers, paper, textile, leather or washing and cleaning - Means.
- the invention also relates to a method for controlling undesired plant growth, a method for controlling unwanted insect or mite infestation on plants and / or for controlling phytopathogenic fungi, and seed treated with the agrochemical formulation.
- Microparticles are known in various embodiments and are used depending on the tightness of the capsule wall for very different purposes. For example, they serve to protect core materials that are to be released only by targeted mechanical destruction of the capsule shell, for example, dye precursors for carbonless paper or encapsulated fragrances.
- Capsule shell materials based on gelatin, polyurethane resin, melamine-formaldehyde resin and polyacrylate are known in such fields of application.
- Other requirements are placed on wall materials for herbal or pharmaceutically active substances as core materials, which require a permeability of the capsule shell which enables a controlled release and the targeted transport of the active substances.
- the capsules produced by chemical processes here also known are mechanical-physical production processes.
- microparticles For the production of microparticles, chemical or physical methods are well known. In physical methods usually dissolved polymers are applied to the material to be encapsulated and transferred by physical methods, such as spray drying or solvent removal, in a solid capsule wall. In chemical methods, the solid capsule wall is formed by chemical reaction, for example by polymerization of monomers, on the material to be encapsulated. An additional physical step to form the solid microparticles is not necessary. Polyester-containing microparticles and their production methods are well known. Such microparticles can be prepared starting from polymeric starting materials for the capsule shell.
- EP 1 421 990 discloses a process for producing microparticles wherein a polyester dispersed in a polyol is emulsified with an enzyme as an effect substance dispersed in a polyol.
- US 4,637,905 discloses a process for the preparation of microparticles having 1 to 2000 microns, wherein a dispersion of polylactic acid with a protein prepared as effect material, evaporates a part of the solvent and finally the concentrated dispersion is added to a third solvent to encapsulate the effect substance.
- WO 2002/069922 discloses microparticles having an oxidoreductase-containing aqueous core and a polyester-containing shell.
- the preparation is carried out by emulsifying an aqueous enzyme solution with a polyester dissolved in an organic solvent, followed by introducing the primary emulsion into an aqueous solvent and then removing the organic solvents.
- DE 102005007374 discloses nanoparticles of the core-shell type.
- the shell defines a polymer that is hydrophobic and biocompatible.
- the polymer is, for example, polyacrylate, polyepoxide, polyurethane or polyester.
- the core defines an active which is enclosed by the polymer of the shell.
- the preparation is carried out by free-radical polymerization, polyaddition, polycondensation or enzymatic or anionic polymerization. Details of the method or examples are not mentioned.
- PCT / EP2008 / 054702 discloses a process for the preparation of microcapsules containing an active ingredient-containing capsule core and a polymer-containing capsule shell comprising the formation of the capsule shell by means of enzyme-catalyzed polymerization of monomers present in an inverse miniemulsion.
- a disadvantage of the known processes is, for example, that the polymers which form the microparticles are prepared separately by polymerization, that the microparticles are not sufficiently stable, or that the release rate of the effect substance can not be controlled.
- the object of the present invention was to provide an improved process for the production of microparticles containing active substances.
- Another aspect of the task was to produce the aforementioned micro-particles under mild reaction conditions, so that even sensitive effect substances can be encapsulated.
- Another aspect was that the later release of the effect substance could be controlled by the manufacturing process and the monomer composition.
- the object was achieved by a process for the preparation of effect material-containing microparticles M comprising A) containing the formation of a crude suspension of microparticles A by enzymatic polyester synthesis in an inverse miniemulsion Enzyme, effect substance and polyester monomers; and B) the polymerization of wall monomers from the group of ethylenically unsaturated monomers, polyisocyanates and / or polyepoxides in the crude suspension of microparticles A.
- microparticles M By means of the method according to the invention, an ensemble of microparticles M is generally produced.
- the inventive method usually leads to the same or similar shaped microparticles.
- Microparts prepared according to the invention can take on any shape. They are preferably substantially spherical, for example, ideally spherical, constructed.
- Effect-containing microparticles M produced according to the invention usually have the structure of a capsule or a matrix particle, preferably a capsule.
- Capsules are typically composed of a polymer-containing capsule shell and an effect-containing capsule core.
- Matrix particles are usually composed of a polymer-containing particle core in which an effect substance is finely distributed.
- a capsule is also to be obtained which comprises at least one capsule shell and at least one capsule core.
- a capsule may have a capsule core and two capsule shells.
- a capsule for example, a plurality of capsule cores, for example two side by side or two nested capsule cores, and a capsule shell, for example, two side by side or nested capsule shells have.
- a capsule comprises a capsule shell and a capsule core.
- the thickness of the capsule shell can vary within a wide range. It is generally from 0.1 to 90%, preferably from 0.5 to 20% of the capsule radius (determined by light / electron microscopy or light scattering).
- the mean diameter of the microparticles M (determinable as Z-agent by light scattering of a 1% strength by weight aqueous dispersion of microparticles, obtainable by dilution of the microparticle suspension with water and optionally separating off an organic phase) can vary widely. It is generally more than 0.1 ⁇ m, preferably more than 0.6 ⁇ m, particularly preferably more than 0.8 ⁇ m.
- the diameter is preferably in the range from 0.1 to 2000 .mu.m, preferably from 0.6 to 1000 .mu.m, in particular from 0.8 to 800 .mu.m.
- a diameter which is in the lower range is preferred if a higher mechanical stability of the microparts is desired.
- a diameter in the higher range is preferred in order to pack as much capsule content as possible in a small amount of wall material.
- the microparticles M usually comprise at least one effect substance.
- the effect substance is present in the particle core or in the capsule core usually in solid, dissolved, e-emulsified or dispersed form.
- the capsule core comprises at least one effect substance and at least one inert substance, which is preferably a liquid.
- all substances in the Compounds present in the process according to the invention are dispersants, polar and / or non-polar liquids, water or the catalytically active enzymes.
- the capsule core comprises at least one effect substance and at least one polar solvent.
- the particle core or capsule core may also contain incompletely polymerized monomer.
- the capsule core comprises at least the polar liquid which forms the disperse phase of the inverse miniemulsion.
- enzymes are used in the process for producing the microparticles M, which catalyze the polymerization of the polyester monomers.
- Enzymes are described using the EC classes developed by the Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (NC-IUBMB) and, of course, it is possible to use a single hydrolase or a mixture of different hydrolases. to use the hydrolases in free and / or immobilized form.
- Suitable hydrolases [EC 3.xxx] are, for example, esterases [EC 3.1.xx], proteases [EC 3.4.XX], hydrolases which react with other CN bonds as peptide bonds [EC 3.5.xx] or hydrolases, the react with acid anhydrides [EC 3.6-xx].
- Carboxylesterases [EC 3.1.1.1], lipases [EC 3.1.1.3] or cutinases [EC 3.1.1.47] are particularly advantageously used according to the invention.
- lipomas from Achromobacter sp., Aspergillus sp., Candida sp., Candida antartica, Mucor sp., Penicilium sp., Geotricum sp., Rhizopus sp., Burkholderia sp., Pseudomonas sp., Pseudomonas cepacia, Thermomyces sp., porcine pancreas or wheat germ and carboxylesterases from Bacillus sp., Pseudomonas sp., Burkholderia sp., Mucor sp., Saccharomyces sp., Rhizopus sp., Thermoanaerobium sp., pig liver or horse liver.
- lipase from Pseudomonas cepacia, Burkholderia platarii or Candida antarctica type B in free or immobilized form (for example Novozym® 435 from Novozymes A / S, Denmark).
- the total amount of enzymes used is generally from 0.001 to 40% by weight, often from 0.1 to 15% by weight and often from 0.5 to 10% by weight, based in each case on the total amount of polyester resin. monomers. The amount depends on the purity of the enzyme used. Technical or immobilized enzymes are usually used in higher amounts than purified enzymes. The skilled person will also adjust the amount of catalyst according to how fast the reaction is to proceed.
- Suitable polyester monomers are, for example, hydroxycarboxylic acid compounds, dialcohol compounds or diacid compounds, especially hydroxycarboxylic acid compounds.
- a combination of the above monomers is also possible, with the combination of dialcohol compounds and diacid compounds being preferred.
- the polyester monomers are combined with a starter monomer which is a hydrogen azide compound such as hydroxy or amino functional compounds or water.
- a suitable starter monomer is a hydroxycarboxylic acid compound, dialcohol compound or diacid compound.
- the starter monomer is preferably a dialcohol compound as described below, especially ethylene glycol, 1,4-butanediol, glycerol, sorbitol, monosaccharide, disaccharide, polysaccharide or hydroxy-functional, dendritic polyesters based on 2,2-dimethylolpropionic acid (Boltorn® types, commercial available from Perstorp).
- a dialcohol compound as described below, especially ethylene glycol, 1,4-butanediol, glycerol, sorbitol, monosaccharide, disaccharide, polysaccharide or hydroxy-functional, dendritic polyesters based on 2,2-dimethylolpropionic acid (Boltorn® types, commercial available from Perstorp).
- Hydroxycarboxylic acid compounds which can be used are the free hydroxycarboxylic acids having at least one free alcohol group and at least one free carboxylic acid group, their C 1 -C 5 -alkyl esters and / or their lactones.
- Examples include glycolic acid, D-, L-, D, L-lactic acid, 6-hydroxyhexanoic acid (6-hydroxycaproic acid), 3-hydroxybutyric acid, 3-hydroxyvaleric acid, 3-hydroxycaproic acid, whose cyclic derivatives such as glycolide (1, 4- Dioxane-2,5-dione), D, L, D, L-dilactide (3,6-dimethyl-1,4-dioxane-2,5-dione), ⁇ -caprolactone, ⁇ -butyrolactone, ⁇ -butyrolactone, ⁇ -dodecanolide (oxacyclotridecan-2-one), ⁇ -undecanolide (oxacyclododecan-2-
- lactones are bis- or tris-lactones which contain two or three lactone groups.
- (2,2'-bis ( ⁇ -caprolactone-4-yl) propane can be used.
- Bis-lactones can be synthesized, for example, according to Palmgren et al., Journal of Polymer Science A, 1997, 35, 1635-1649.
- esters of carbonic acid especially linear and cyclic aliphatic carbonates, preferably C 1 to C 6 -alkyl esters of carbonic acid, in particular trimethylene carbonate Carbonates which do not react with the particular enzyme, for example propylene carbonate, are unsuitable as monomers
- Hydroxycarboxylic acid compounds which may also be used are the thiocarboxylic acid analogues of the abovementioned hydroxycarboxylic acid and their esters and thiolactones.Of course, it is also possible to use mixtures of different hydroxycarboxylic acid compounds
- Preferred hydroxycarboxylic acid compounds are lactones, in particular C 2 -C 6 -alkylene lactones, very particularly preferably ⁇ -caprolactone.
- dicarboxylic acid compounds it is possible in principle to use all C 2 -C 4 aliphatic, C 3 -C 20 cycloaliphatic, aromatic or heteroaromatic compounds which have at least two carboxylic acid groups (carboxy groups, -COOH) or derivatives thereof.
- Particularly suitable derivatives are C 1 -C 10 -alkyl, preferably methyl, ethyl, n-propyl or isopropyl mono- or diesters of the aforementioned dicarboxylic acids, and also the corresponding dicarboxylic acid anhydrides.
- dicarboxylic acid compounds are ethanedioic acid (oxalic acid), propanedioic acid (malonic acid), butanedioic acid (succinic acid), pentanedioic acid (glutaric acid), hexanedioic acid (Adipic acid), heptanedioic acid (pimelic acid), octanedioic acid (suberic acid), nonanedioic acid (azelaic acid), decanedioic acid (sebacic acid), undecanedioic acid, dodecanedioic acid, tridecanedioic acid (brassylic acid), C 32-dimer fatty acid, benzene-1,2-dicarboxylic acid (phthalic acid), Benzene-1,3-dicarboxylic acid (isophthalic acid) or benzene-1,4-dicarboxylic acid (terephthalic acid), the
- Terephthal Acidimethylester and their anhydrides, for example, butanedicarboxylic acid, pentanedicarboxylic or Phthalklareandhydrid.
- dicarboxylic acid compounds can be used.
- ONcoesters and polyesters having at least two free carboxy groups, in particular carboxy-terminated oligo- and polyesters, can likewise be used as the dicarboxylic acid component.
- esters of polycarboxylic acids such as citric acid and butanetetracarboxylic acid can be used.
- the free dicarboxylic acids especially C 4 to C 36 aliphatic dicarboxylic acids, in particular butanedioic acid, hexanedioic acid, decanedioic acid, dodecanedioic acid or their corresponding dimethyl and diethyl esters.
- diol compounds it is possible to use branched or linear alkanes having 2 to 18 carbon atoms, preferably 4 to 14 carbon atoms, cycloalkanes having 5 to 20 carbon atoms or aromatic compounds which contain at least two alcohol groups.
- alkanediols examples include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1, 8-octanediol, 1, 9-nonanediol, 1, 10-decanediol, 1, 11-undecanediol, 1, 12-dodecanediol, 1, 13-tridecanediol, 2,4-dimethyl-2-ethyl-1, 3 hexanediol, 2,2-dimethyl-1,3-propanediol (neopentyl glycol), 2-ethyl-2-butyl-1,3-propanediol, 2-ethyl-2-isobutyl-1,3-propan
- Particularly suitable are ethylene glycol, 1, 3-propanediol, 1, 4-butanediol and 2,2-dimethyl-1, 3-propanediol, 1, 6-hexanediol or 1, 12-dodecanediol.
- cycloalkanediols are 1, 2-cyclopentanediol, 1, 3-cyclopentanediol, 1, 2-cyclohexanediol, 1, 3-cyclohexanediol, 1, 4-cyclohexanediol, 1, 2-cyclohexanedimethanol (1, 2-dimethylolcyclohexane) , 1, 3-cyclohexanedimethanol (1,3-dimethylolcyclohexane), 1,4-cyclohexanedimethanol (1,4-dimethylolcyclohexane) or 2,2,4,4-tetramethyl-1,3-cyclobutanediol.
- aromatic diols examples include 1, 4-dihydroxybenzene, 1, 3-dihydroxybenzene, 1, 2-dihydroxybenzene, bisphenol A (2,2-bis (4-hydroxyphenyl) -propane), 1, 3-dihydroxynaphthalene, 1, 5 Dihydroxynaphthalene or 1, 7-dihydroxynaphthalene.
- polyether diols for example diethylene glycol, triethylene glycol, polyethylene glycol (with more than 4 ethylene oxide units), propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol (with more than 4 propylene oxide units) and polytetrahydrofuran (polyTHF), in particular diethylene glycol, triethylene glycol and polyethylene glycol (with more than 4 ethylene oxide units) are used.
- poly-THF polyethylene glycol or polypropylene glycol find compounds whose number average molecular weight (Mn) is usually in the range of 200 to 10,000, preferably from 600 to 5000 g / mol.
- oligoesters and polyesters having at least two free alcohol groups preferably dihydroxy-terminated oligo- and polyesters.
- dendrimers which have at least two primary or secondary free alcohol groups.
- polycarbonates which have at least two primary or secondary free alcohol groups.
- suitable diol compounds having more than two alcohol groups are glycerol, sorbitol, trimethylolpropane, pentaerythritol, monosaccharides such as fructose, glucose or mannose, disaccharides such as sucrose, oligosaccharides and their substitution products, or cellulose derivatives such as acetates.
- diol compounds it is also possible to use one of the abovementioned diol compounds analogous dithiol. Of course, it is also possible to use mixtures of the abovementioned diol compounds or dithiols.
- Preferred diols are aliphatic alkanediols and polyether diols, more preferably linear and branched aliphatic alkanediols having 2 to 18 carbon atoms, in particular ethylene glycol, 1, 4-butanediol, 1, 6-hexanediol, sorbitol and neopentyl glycol.
- linear, branched or crosslinked polyesters can be formed, depending on whether difunctional monomers or higher-functional monomers are used.
- the polyester monomers are generally in the reaction mixture in step A) to 0.1 to 20 wt .-%, preferably from 0.5 to 10 wt .-%, in particular to 1 to 5 wt .-% based on the total batch contain.
- at least one lactone is present at 0.1 to 20% by weight, preferably at 0.5 to 10% by weight, in particular at 1 to 5% by weight, based on the overall batch in step A).
- dispersants can be used. These may in principle be protective colloids, emulsifiers or mixtures thereof. It goes without saying that the emulsifiers and / or protective colloids are selected so that they are compatible in particular with the enzymes used and do not deactivate them.
- the polymerization can be carried out in the presence of protective colloids, if appropriate also in addition to emulsifiers. They generally have average molecular weights Mw of above 500, preferably of more than 1000 g / mol.
- protective colloids are polyvinyl alcohols, cellulose derivatives such as carboxymethyl cellulose, polyvinyl pyrrolidone, polyethylene glycols, graft polymers of vinyl acetate and / or
- emulsifiers are used as dispersants.
- emulsifiers are used whose relative molecular weights, in contrast to the protective colloids, are usually below 1000 g / mol. They may be anionic, cationic or nonionic in nature.
- anionic emulsifiers are compatible with each other and with nonionic emulsifiers. The same applies to cationic emulsifiers, while anionic and cationic emulsifiers are usually incompatible with each other.
- the polymerization can also be carried out in the presence of finely divided, water-insoluble inorganic emulsifiers (so-called Pickering emulsifiers), for example barium sulfate.
- Finely divided, water-insoluble inorganic emulsifiers for example barium sulfate.
- Common nonionic emulsifiers are, for example, ethoxylated mono-, di- and tri-alkylphenols (degree of ethoxylation from 3 to 50, alkyl radical: C 4 to C 12) and ethoxylated fatty alcohols (degree of ethoxylation from 3 to 80, alkyl radical: Cs to C 36).
- Lutensol® A grades C12 to Cu fatty alcohol ethoxylates, degree of ethoxylation from 3 to 8
- Lutensol® AO grades C13 to Cis oxo alcohol ethoxylates, ethoxylation levels of 3 to 30
- Lutensol® AT grades C16 to Cis fatty alcohol ethoxylates, degree of ethoxylation from 1 to 80
- Lutensol® ON grades C10 oxo alcohol ethoxylates, degree of ethoxylation from 3 to 11
- Lutensol® TO grades C13 oxo alcohol ethoxylates, degree of ethoxylation from 3 to 20 from BASF SE.
- Typical anionic emulsifiers are, for example, alkali metal and ammonium salts of alkyl sulfates (alkyl radical: C8 to C12), of sulfuric monoesters of ethoxylated alkanols (degree of ethoxylation from 4 to 30, alkyl radical: C12 to de) and ethoxylated alkylphenols (degree of ethoxylation from 3 to 50, alkyl radical: C 4 to C 12), of alkylsulfonic acids (alkyl radical: C 12 to C 18) and of alkylarylsulfonic acids (alkyl radical: Cg to Cis).
- Further anionic emulsifiers further compounds of the general formula (I)
- R 1 and R 2 are H atoms or C 4 - to C 24 -alkyl and not simultaneously H-
- M 1 and M 2 may be alkali metal ions and / or ammonium ions.
- R 1 and R 2 are preferably linear or branched alkyl radicals having 6 to 18 C atoms, in particular having 6, 12 and 16 C atoms or hydrogen, wherein R 1 and R 2 are not both simultaneously H atoms.
- M 1 and M 2 are preferably sodium, potassium or ammonium, with sodium being particularly preferred.
- Particularly advantageous compounds (I) are those in which M 1 and M 2 are sodium, R 1 is a branched alkyl radical having 12 C atoms and R 2 is an H atom or R 1 .
- technical mixtures are used which have a proportion of 50 to 90% by weight of the monoalkylated product, such as, for example, Dowfax® 2A1 (trademark of the Dow Chemical Company).
- Suitable cationic emulsifiers are generally ce- to cis-alkyl-, alkylaryl- or heterocyclic radical-containing cationic salts, for example primary, secondary, tertiary or quaternary ammonium salts, alkanolammonium salts, pyridinium salts, imidazolinium salts, oxazolinium salts, morpholinium salts, thiazolinium salts and salts of amine oxides, quinolinium salts, isoquinolinium salts, tropylium salts, sulfonium salts and phosphonium salts.
- Examples include dodecylammonium acetate or the corresponding sulfate, the sulfates or acetates of the various 2- (N, N, N-trimethylammonium) ethylparaffinklar, N-cetylpyridinium, N-Laurylpyridiniumsulfat and N-cetyl-N, N, N-trimethylammonium sulfate, N-dodecyl-N, N, N-trimethylammonium sulfate, N-octyl-N, N, N-trimethylammonium sulfate, N, N-distearyl-N, N-dimethylammonium sulfate and the gemini surfactant N, N '- ( Lauryldimethyl) ethylenediamine disulfate, ethoxylated tallow fatty alkyl N-methylammonium sulfate, and ethoxylated oleylamine (for
- anionic counter groups are as low as possible nucleophilic, such as perchlorate, sulfate, phosphate, nitrate and carboxylates, such as acetate, trifluoroacetate, trichloroacetate, propionate, oxalate, citrate, benzoate, as well as conjugated anions of organosulfonic acids, such as methyl sulfonate, Trifluoromethylsulfonate and para-toluenesulfonate, furthermore tetrafluoroborate, tetraphenylborate, tetrakis (pentafluorophenyl) borate, tetrakis [bis (3,5-trifluoromethyl) phenyl] borate, hexafluorophosphate, hexafluoroarsenate or hexafluoroantimonate.
- nucleophilic such as perchlorate, sulfate, phosphate, n
- Preferred emulsifiers are nonionic emulsifiers, in particular ethoxylated alcohols and sorbitan esters, particularly preferably ethoxylated fatty alcohols and sorbitan fatty acid esters.
- Very particularly preferred mixtures include ethoxylated alcohols and sorbitan esters.
- the mixtures contain ethoxylated alcohols and sorbitan esters.
- a polymer based on the ene reaction product of polyisobutylene and maleic anhydride (PIBSA) and di (alkyl) ethanolamine is suitable.
- block copolymers are suitable, as described in Macromolecules 38 (16), 6882-6887, block copolymers based on isoprene and methyl methacrylate, as described in US Pat WO 2008/009424, or poly ((ethylene-co-butylene) -block-ethylene oxide).
- the emulsifiers preferably used as dispersants are advantageously in a total amount of 0.005 to 20 wt .-%, preferably 0.01 to 15 wt .-%, in particular 0.1 to 10 wt .-%, each based on the total batch in step A. ).
- the total amount of the protective colloids used as dispersing agents in addition to or instead of the emulsifiers is often from 0.1 to 10% by weight and frequently from 0.2 to 7% by weight, based in each case on the overall batch in step A).
- the inverse miniemulsion according to the invention in which the polyester monomers are mostly present, comprises a continuous nonpolar phase and a discontinuous polar phase.
- the polar phase comprises a polar liquid and the non-polar phase a non-polar liquid.
- the effect substance is present essentially in the discontinuous phase in solid, dissolved, emulsified or dispersed form.
- the polyester monomers, dispersants or enzymes can be present both distributed in one of the two phases as well as in both phases, or at the interface of the two phases.
- the polyester monomer is at least 70% by weight, preferably at least 80% by weight and in particular at least 90% by weight, based in each case on the total amount of the polyester monomer in step A), in the polar phase.
- the polar liquid consists of at least one polyester monomer and at least one effect substance.
- the mean size of the droplets of the discontinuous phase of the inverse miniemulsion according to the invention can preferably be determined according to the principle of quasi-elastic dynamic light scattering on a 1% by weight miniemulsion obtainable by diluting the inverse miniemulsion with the corresponding continuous phase and, if appropriate, separating an organic phase , determine (the so-called Z-median droplet diameter d z of the unimodal analysis of the autocorrelation function). Further determination methods are light or electron microscopy, as well as Feldflußfr sotechnik.
- the values for d z thus determined for the inverse miniemulsions are normally below 10000 nm, often below 1000 nm, usually below 500 nm.
- the d z range from 2000 nm to 1000 nm is favorable in accordance with the invention. In the normal case, d z is according to the invention Inverse miniemulsion to be used over 40 nm.
- Suitable polar liquids are those whose solubility in the continuous nonpolar phase under reaction conditions is below 40% by weight, preferably below 10% by weight and in particular below 1% by weight (in each case based on the total amount of the continuous phase) that a separate discontinuous polar phase is present.
- the polar liquid dissolves at 20 ° C. the polyester monomer at most 10% by weight, preferably at most up to 3% by weight and especially at most up to 0.5% by weight, in each case based on the total weight of the polyester monomer.
- Suitable polar liquids are, for example, monools, such as Cs-C ⁇ -alkanols, in particular tert-butanol and tert. -Amyl alcohol, pyridine, poly-C 1 -C 4 -alkylene glycol di-C 1 -C 4 -alkyl ethers, in particular polyethylene glycol di-C 1 -C 4 -alkyl ethers, such as e.g.
- Dimethoxymethane diethylene glycol dimethyl ether, polyethylene glycol dimethyl ether 500, C 2 -C 4 -alkylene carbonates, in particular propylene carbonate, C 3 -C 6 -alkyl acetic acid esters, in particular tert-butyl acetic acid esters, acetone, 1, 4-dioxane, 1, 3-dioxolane, tetrahydrofuran ran, dimethoxymethane, dimethoxyethane, aqueous buffer or water.
- Suitable polar liquids are also the abovementioned polyester monomers or mixtures thereof.
- the polar liquid may also comprise or may consist of the effect substance used.
- Preferred polar liquid is propylene carbonate and propylene carbonate containing mixtures.
- the polar liquid is the polyester monomer.
- the polar liquid comprises less than 5% by weight, preferably less than 1% by weight and in particular less than 0.1% by weight of water.
- the polar liquid contains water, it is advantageous if the aqueous reaction medium at room temperature (20 to 25 0 C) has a pH of 2 to 1 1, often from 3 to 9 and often from 6 to 8.
- a pH is set in which the enzyme has a high catalytic activity and a long service life.
- acid for example sulfuric acid
- bases for example aqueous solutions of alkali metal hydroxides, in particular sodium or potassium hydroxide
- buffer substances for example potassium dihydrogen phosphate / disodium hydrogen phosphate, acetic acid / sodium acetate, ammonium hydroxide / ammonium chloride Potassium dihydrogen phosphate / sodium hydro
- hydrophilic agents are, for example, organic or inorganic salts or uncharged, very polar compounds.
- inorganic salts are sodium nitrite, sodium chloride, potassium chloride, lithium chloride, rubidium chloride.
- organic salts are trialkylammonium salts, ionic
- Liquids such as ethyl-methylimidazolium salts, or oligomers with stoichiometric proportions of anionic and cationic groups in the main or side chain te. Preference is given to hydrophiles which do not reduce the catalytic activity of the enzymes.
- Suitable non-polar liquids are those whose solubility in the discontinuous polar phase under reaction conditions below 10 wt .-%, preferably below 1 wt .-% and in particular below 0.1 wt .-% (in each case based on the total amount of the continuous phase ), so that there is a separate continuous polar phase.
- Suitable non-polar liquids are, for example, liquid aliphatic or aromatic hydrocarbons having 5 to 30 C atoms, for example n-pentane and isomers, cyclopentane, n-hexane and isomers, cyclohexane, n-heptane and isomers, n-octane and isomers, n-nonane and isomers, n-decane and isomers, n-dodecane and isomers, n-tetradecane and isomers, n-hexadecane and isomers, n-octadecane and isomers, benzene, toluene, ethylbenzene, cumene, o-, m- or p-xylene, mesitylene.
- hydrocarbon mixtures in the boiling range from 30 to 250 0 C come as partially hydrogenated petroleum distillates (eg Isopar® brands Fa. Exxon Mobil).
- olefins for example polyisobutylenes or C6 to C30 alpha-olefins.
- hydroxy compounds such as saturated and unsaturated fatty alcohols having 10 to 28 carbon atoms, for example n-dodecanol, n-tetradecanol, n-hexadecanol and their isomers or cetyl alcohol, esters, such as fatty acid esters having 10 to 28 carbon atoms in the acid part and 1 to 10 carbon atoms in the alcohol part or esters of carboxylic acids and fatty alcohols having 1 to 10 carbon atoms in the carboxylic acid part and 10 to 28 carbon atoms in the alcohol part.
- esters such as fatty acid esters having 10 to 28 carbon atoms in the acid part and 1 to 10 carbon atoms in the alcohol part or esters of carboxylic acids and fatty alcohols having 1 to 10 carbon atoms in the carboxylic acid part and 10 to 28 carbon atoms in the alcohol part.
- non-polar liquids are paraffin oil (linear hydrocarbon mixtures), silicone oil (polysiloxane), perfluorinated hydrocarbons, fluorosilicone oil, perfluorinated polyethers, fluorosilane or SiIo- xan, such as dimethylsiloxane.
- Preferred non-polar liquids are liquid aliphatic and aromatic hydrocarbons having 5 to 30 carbon atoms, in particular partially hydrogenated mineral oil distillates.
- nonpolar liquids are paraffin oil.
- the total amount of polar and non-polar liquids is chosen such that the total batch in step A) reaches 100% by weight. It is generally from 10 to 90 wt .-%, preferably from 40 to 70 wt .-% based on the total batch.
- the quantitative ratio of polar to nonpolar liquid is chosen so that a discontinuous phase is formed which essentially contains the polar liquid.
- 20 to 80 preferably 40 to 70 wt .-% of nonpolar liquid used, each based on the total batch.
- from 20 to 80% by weight, preferably from 30 to 60% by weight, of polar liquid is used, in each case based on the overall batch.
- from 20 to 80 preferably from 35 to 55,% by weight of hydrocarbon mixtures and from 20 to 70% by weight, preferably from 30 to 60% by weight, of propylene carbonate are used, in each case based on the overall batch. Care must be taken to ensure that the miniemulsions do not undergo a phase reversal, ie that the hydrophobic continuous phase does not become the disperse phase.
- effect substances are to be understood in the context of the invention substances which cause the user desired effects in the commercial application of the product according to the invention.
- Effect substances are, for example, colorants, cosmetics, pharmaceuticals, biocides, crop protection agents, agrochemical adjuvants, fertilizers, additives for food or animal feed, auxiliaries for polymers, paper, textile, leather or detergents and cleaners.
- the person skilled in the art can select the appropriate effect substance on the basis of his general specialist knowledge.
- colorants are dyes, printing inks, pigments, UV absorbers, optical brighteners or IR dyes. While organic dyes have an absorption maximum in the wavelength range from 400 to 850 nm, optical brighteners have one or more absorption maxima in the range from 250 to 400 nm. Optical brighteners emit fluorescence radiation in the visible range when irradiated with UV light. Examples of optical brighteners are compounds from the classes of bisstyrylbenzenes, stilbenes, benzoxazoles, coumarins, pyrenes and naphthalenes. Also suitable are markers for liquids, for example mineral oil markers. UV absorbers are generally understood as UV-absorbing compounds which deactivate the absorbed radiation without radiation. Such compounds are used for example in sunscreens and for the stabilization of organic polymers.
- Cosmetics are substances or preparations of substances which are exclusively or predominantly intended to be externally on the human body or in the oral cavity for the purpose of cleaning, care, protection, maintenance of good condition, perfuming, alteration of the appearance or to it to be applied, to influence the body odor.
- anti-insect agents such as Icaridin® or N, N-diethyl-meta-toluamide (DEET®).
- biocides heavy metal-containing biocides such as N- (cyclo-hexyldiazeniumdioxy) tributyltin, bis-N- (cyclohexyldiazeniumdioxy) copper (CuHDO);
- Metallic soaps such as tin, copper, zinc naphthenate, octoate, 2-ethylhexanoate, oleate, phosphate, benzoate, metal salts such as copper hydroxycarbonate, sodium dichromate, potassium dichromate, potassium chromate, mat, copper sulfate, copper chloride, copper borate, zinc fluorosilicate, copper fluorosilicate, copper salt of 2-pyridinethiol-1-oxide; Oxides as well as tributyltin oxide, CU2O, CuO, ZnO; Ag, Zn or Cu-containing zeolites may be contained alone or enclosed in polymeric active substances.
- Suitable biocides are preferably algicides such as diur
- biocides are bis-N- (cyclohexyldiazeniumdioxy) copper, dithianone, bronopol, sodium chlorite (NaCIO 2 ), 2,4-dichlorobenzyl alcohol.
- microcapsules according to the invention comprising biocides can be used everywhere, where it is possible to bacteria-free, algae and fungus-free, d. H. microbicidal surfaces or surfaces with non-stick properties arrives. They can be used in the field
- Air conditioners air conditioners, ion exchangers, service water, solar systems, heat exchangers, bioreactors, membranes, cooling water treatment;
- Suitable crop protection agents are acaricides, algicides, aphicides, bactericides, fungicides, herbicides, insecticides, molluscicides, nematicides, germination inhibitors, safeners or growth regulators.
- Fungicides are compounds that kill fungi and their spores or inhibit their growth.
- Insecticides are compounds that are especially effective against insects and their developmental forms.
- Under Herbicides are compounds that are active against generally all wild and cultivated plants that are undesirable at their respective location (weeds).
- fertilizers are mineral single or multi-nutrient fertilizers, organic and organic-mineral fertilizers or fertilizers with trace nutrients.
- the effect substances are pesticides or mixtures of pesticides.
- the crop protection agents are preferably herbicides, growth regulators, insecticides or fungicides. It is generally known against which unwanted plants, insects or fungi a crop protection agent can be advantageously used.
- the following list of plant protection products indicates, but is not intended to be limited to, any active ingredients.
- fungicide for example: A) strobilurins:
- Azoxystrobin Dimoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Metomino Strobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyribencarb, Trifloxystrobin, 2- (2- (6- (3-Chloro-2-methyl-phenoxy) -5-fluoro) pyrimidin-4-yloxy) -phenyl) -2-methoxy-imino-N-methyl-acetamide, 2- (ortho - ((2,5-dimethylphenyl-oxymethylene) -phenyl) -3-methoxy-acrylic acid methyl ester, 3-methoxy- Methyl 2- (2- (N- (4-methoxy-phenyl) -cyclopropanecarboximidoylsulfanylmethyl) -phenyl) acrylate, 2- (2- (3- (2,6-dichlorophenyl) -1-methyl-allylidene
- Benzoic acid amides flumetover, fluopicolide, fluopyram, zoxamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide;
- carboxamides carpropamide, diclocymet, mandipropamide, oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropanecarboxamide;
- Triazoles azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole , Prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1- (4-chloro-phenyl) -2 - ([1, 2,4] triazol-1-yl) -cycloheptanol;
- - imidazoles cyazofamide, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizole;
- Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole; - Other: ethaboxam, etridiazole, hymexazole, 2- (4-chloro-phenyl) -N- [4- (3,4-dimethoxyphenyl) -isoxazol-5-yl] -2-prop-2-ynyloxy-acetamide ;
- Pyridines fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine, 3- [5- (4-methyl-phenyl) -2, 3-dimethylisoxazolidin-3-yl] -pyridine, 2,3,5,6-tetrachloro-4-methanesulfonylpyridine, 3,4,5-trichloropyridine-2,6-dicarbonitrile, N- (1 (5-Bromo-3-chloro-pyridin-2-yl) -ethyl) -2,4-dichloronotinamide, N - ((5-bromo-3-chloro-pyridin-2-yl) -methyl) -2,4 -dichlornicotinamid;
- Pyrimidines Bupirimat, Cyprodinil, Diflumetorim, Fenarimol, Ferimzone, Mepanipyrim, Nitrapyrin, Nuarimol, Pyrimethanil; - piperazines: triforins;
- - morpholines aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; - piperidines: fenpropidine;
- Dicarboximides fluorimide, iprodione, procymidone, vinclozolin;
- non-aromatic 5-membered heterocycles famoxadone, fenamidone, flutianil, octhilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydropyrazole-1-thiocarboxylic acid allyl ester;
- Thio and dithiocarbamates Ferbam, Mancozeb, Maneb, Metam, Methasulphocarb, Metiram, Propineb, Thiram, Zineb, Ziram; Carbamates: Diethofencarb, Benthiavalicarb, Iprovalicarb, Propamocarb, Propamocarb hydrochloride, Valiphenal, N- (1- (1- (4-cyanophenyl) ethanesulfonyl) -but-2-yl) carbamic acid- (4-fluorophenyl) ester;
- Guanidines dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadin tris (albesilat);
- antibiotics kasugamycin, kasugamycin hydrochloride hydrate, polyoxines, streptomycin, validamycin A;
- Sulfur-containing heterocyclyl compounds dithianone, isoprothiolanes
- Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;
- Organochlorine compounds chlorothalonil, dichlofluanid, dichlorophene, flusulphamide, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phthalide, quintozene, thiophanate-methyl, tolylfluanid, N- (4-chloro-2-nitro-phenyl) -N-ethyl- 4-methyl-benzenesulfonamide;
- Inorganic active ingredients phosphorous acid and its salts, Bordeaux broth, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur; - Other: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamine, metrafenone, mildiomycin, oxine-copper, prohexadione-calcium, spiroxamine, tolylfluanid, N- (cyclopropylmethoxyimino- (6-difluoromethoxy-2,3-difluorophenyl) - methyl) -2-phenylacetamide, N '- (4- (4-chloro-3-trifluoromethylphenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamide, N' - (4- (4-Fluoro-3-trifluoromethylphenoxy) -2,5
- growth regulators which can be used are: abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butraline, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dimethipine, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, For- chlorfenuron, gibberellic acid, inabenfid, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), metconazole, naphthalene acetic acid, N-6-benzyladenine, paclobutrazole, prohexadione (prohexadione-calcium), prohydrojasmon, thidiazorone, Tri-penthenol, tributyl phosphorot
- acetamides acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamide, pretilachlor, propachlor, thenylchloro;
- Amino acid analogues bilanafos, glyphosate, glufosinate, sulfosate;
- Aryloxyphenoxypropionates Clodinafop, Cyhalofop-butyl, Fenoxaprop, Fluazifop, Haloxyfop, Metamifop, Propaquizafop, Quizalofop, Quizalofop-P-tefuryl;
- Bipyridyls diquat, paraquat;
- Carbamates and thiocarbamates asulam, butylates, carbamides, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinates, orbencarb, phenmedipham, prosulphocarb, pyributicarb, thiobencarb, triallates; - cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim;
- Diphenyl ether acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;
- Hydroxybenzonitriles bromoxynil, dichlobenil, loxynil;
- Imidazolinone imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr;
- Phenoxyacetic acids clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, mecoprop;
- - Pyrazines Chloridazon, Flufenpyr-ethyl, Fluthiacet, Norflurazon, Pyridate;
- - pyridines aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, pilinoram, picolinafen, thiazopyr;
- Sulfonylureas amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, lodosulfuron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosul furon, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 - ((2-chloro-6-prop
- acetolactate synthase bispyribac sodium, cloransulam methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, orthosulphamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxime, pyriftalid, pyriminobac-methyl, pyrimisulphane, pyrithiobac, pyroxasulphone, pyroxsulam;
- insecticide for example:
- Organo (thio) phosphates acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulphoton, ethion, fenitrothion, fenthione, isoxathione, malathion, methamidophos, methidathion , Methyl parathion, mevinphos, monocrotophos, oxydemeton
- Carbamates alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb,
- - pyrethroids allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalo- thrin, permethrin, prallethrin , Pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin,
- Insect growth inhibitors a) chitin synthesis inhibitors: benzoylureas: chlorofluorazuron, cyramazine, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; Buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozid, methoxyfenozide, tebufenozide, azadirachtin; c) Juvenoids: Pyriproxyfen, Methoprene, Fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat; Nicotine receptor agonists / antagonists: clothianidin, dinotefuran,
- GABA antagonists endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, 5-amino-1- (2,6-dichloro-4-methylphenyl) -4-sulfinamoyl-1H-pyrazole-3-thiocarbon acid amide; Macrocyclic lactones: Abamectin, Emamectin, Milbemectin, Lepimectin, Spinosid, Spinetoram;
- Inhibitors of oxidative phosphorylation cyhexatin, diafenthiuron, fenbutatin oxide, propargite; Inhibitors of the sloughing of insects: Cryomazine;
- Inhibitors of mixed function oxidases piperonyl butoxide
- the crop protection agents are preferably herbicides. In a further preferred embodiment, the crop protection agents are preferably insecticides. In a further preferred embodiment, the crop protection agents are preferably fungicides. In a further preferred embodiment, the fungicides are preferably azoles. In a further preferred embodiment, the azoles are preferably triticonazole, epoxiconazole, fluquinconazole or metconazole.
- agrochemical adjuvants are compounds or mixtures of compounds which by themselves have no pesticidal activity but increase the efficacy of a pesticide.
- penetration enhancers are examples. Suitable penetration promoters are all those substances which are usually used to improve the penetration of agrochemical active substances into plants. Penetration promoters are in this context defined by the fact that they can penetrate from the aqueous spray mixture and / or from the spray coating in the cuticle of the plant and thereby increase the material mobility (mobility) of active ingredients in the cuticle.
- suitable effect substances are additives for food or animal feed, such as food colorants, amino acids, vitamins, preservatives, antioxidants, odorants or flavorings.
- auxiliaries for polymers are flame retardants, viscosity improvers or polar liquids, as they can be used in the discontinuous phase.
- auxiliaries for paper are alkenylsuccinic anhydrides or dialkyldiketenes.
- auxiliaries for detergents and cleaners are surfactants or emulsifiers, as can also be used as dispersants in the inverse miniemulsion.
- enzymes such as hydrolases or amidases can be used as auxiliaries.
- Preferred effect substances are biocides, pesticides and fertilizers. In one embodiment, the effect substances are pesticides. In another embodiment, the effect substances are biocides. In another embodiment, the effect substances are agrochemical adjuvants.
- the effect materials can be used in pure form, technical grade, as an extract or in mixture with other effect substances.
- the effect substances are dissolved or in solid form in the dispersed phase.
- the total amount of effect substances is from 0.1 to 90% by weight, preferably from 5 to 50% by weight, based on the total batch in step A).
- the effect substances can be released from the microparticles by diffusion from the microparticle or by degradation of the microparticle.
- the release path can be selectively controlled by internal and external influences which influence the diffusion or degradation.
- additives for example preservatives, thickeners, release agents or protective colloids and emulsifiers, which can also be used in the process according to the invention, are known to the person skilled in the art and are added in customary amounts, depending on the intended use, after preparation of the microparticles.
- the wall monomers are selected from the group of ethylenically unsaturated monomers, polyisocyanates and / or polyepoxides.
- the polyisocyanates are preferably used in combination with another wall monomer, such as ethylenically unsaturated monomers and polyisocyanates, polyisocyanates and polyols, polyisocyanates and polyamines.
- Preferred wall monomers are ethylenically unsaturated monomers, ethylenically unsaturated monomers and polyisocyanates, monoethylenically and multiply ethylenically unsaturated monomers, polyisocyanates and polyols, polyisocyanates and polyamines, and polyepoxides and polyamines.
- Particularly preferred wall monomers are ethylenically unsaturated monomers, and ethylenically unsaturated monomers and polyisocyanates.
- Especially preferred wall monomers are ethylenically
- Suitable ethylenically unsaturated monomers are radically polymerizable monomers having at least one, preferably one, CC double bond.
- Preferred ethylenically unsaturated monomers are (meth) acrylic acid, (meth) acrylates, (meth) acrylamide or vinyllactams, in particular (meth) acrylic acid, (meth) acrylates, (meth) acrylamide.
- acrylic acid and its esters methacrylic acid and its esters, maleic acid and its esters, styrene, butadiene, isoprene, vinyl acetate, vinyl propionate, vinylpyridine, vinyl chloride, vinylidene dichloride, acrylonitrile, methacrylamide, itaconic acid, maleic anhydride, N-vinylpyrrolidone, and acrylamido-2-methyl propanesulfonic acid, N-methylolacrylamide, N-methylolmethacrylamide, dimethylaminoethyl methacrylate and diethylaminoethyl methacrylate.
- esters of acrylic acid or methacrylic acid are C 1 -C 24 -alkyl esters, especially hydroxy-functional alkyl esters, especially hydroxy-C 2 -C 6 -alkyl esters such as 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate , 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate.
- water-soluble ethylenically unsaturated monomers having a solubility of at least 5% by weight in water are suitable.
- examples are acrylamide, methacrylamide, acrylic acid, methacrylic acid, salts of acrylamido-2-methylpropanesulfonic acid, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate or 3-hydroxypropyl methacrylate.
- Very particularly preferred ethylenically unsaturated monomers are hydroxy-functional C 2 -C 6 -alkyl esters of acrylic acid or methacrylic acid, and vinylpyrrolidone, especially 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate or 3-hydroxypropyl methacrylate.
- Suitable polyisocyanates are aliphatic and aromatic isocyanates having at least two, preferably two to four, particularly preferably two to three isocyanate groups.
- polyisocyanates are aromatic isocyanates such as 2,4-tolylene diisocyanate (2,4-TDI), 2,4'-diphenylmethane diisocyanate (2,4'-MDI) and so-called TDI mixtures (mixtures of 2,4-tolylene diisocyanate and 2,6-tolylene diisocyanate).
- aliphatic isocyanates are: 1,4-butylene diisocyanate, hexamethylene diisocyanate (HDI), 1,12-dodecamethylene diisocyanate, 1,10-decamethylene diisocyanate, 2-butyl-2-ethylpentamethylene diisocyanate, 2,4,4- or 2-butene , 2, 4-trimethyl hexamethylene diisocyanate, isophorone diisocyanate (IPDI), 2-isocyanatopropyl cyclohexyl isocyanate, 2,4'-methylenebis (cyclohexyl) diisocyanate and 4-methylcyclohexane-1, 3-diisocyanate (H-TDI).
- HDI hexamethylene diisocyanate
- IPDI isophorone diisocyanate
- oligo-cyanates are oligo-cyanates and mixtures thereof.
- the number of isocyanate groups is usually determined via the NCO content and thus calculates the average number of isocyanate groups.
- This average number of isocyanate groups is typically at least two, preferably two to four, more preferably two to three.
- Preferred oligoisocyanates are based on the abovementioned aromatic and / or aliphatic polyisocyanates, especially on diphenylmethane diisocyanate and / or hexamethylene diisocyanate.
- Such oligoisocyanates are commercially available, for example, as Lupranat® M20S from BASF SE.
- Preferred polyisocyanates are tolylene diisocyanate (2,4-TDI), 2,4'-diphenylmethane diisocyanate (2,4'-MDI), hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), and oligoisocyanates. Particularly preferred are oligoisocyanates.
- the polyisocyanates can be prepared in the absence or preferably in the presence of at least one polyurethane catalyst. Suitable polyurethane catalysts are, for example, all catalysts customarily used in polyurethane chemistry, such as organic amines, in particular tertiary aliphatic, cycloaliphatic or aromatic amines, and Lewis-acidic organic metal compounds.
- Suitable Lewis acidic organic metal compounds are tin compounds, for example tin (II) salts of organic carboxylic acids, for example tin (II) acetate, tin (II) octoate, tin (II) ethyl hexoate and tin (II ) -Aurate and the dialkyltin (IV) derivatives of organic carboxylic acids, eg dimethyltin diacetate, dibutyltin diacetate, dibutyltin dibutyrate, dibutyltin bis (2-ethylhexanoate), dibutyltin dilaurate, dibutyltin maleate, dioctyltin dilaurate and dioctyltin diacetate.
- Metal complexes such as acetylacetonates of iron, titanium, zinc, aluminum, zirconium, manganese, nickel and cobalt are also possible.
- Suitable polyepoxides are compounds having at least two, preferably two to three epoxide groups. Examples of these are epoxides derived from bisphenol A, such as bisphenol A diglycidyl ether or epoxides of the epichlorohydrin-substituted bis- or polyphenols type (epoxides having a degree of polymerization of 1 to 2, sold under the name Epikote® E 828 by Shell ), or tetraglycidylmethylenedianiline (eg LY 1802 from Ciba).
- bisphenol A such as bisphenol A diglycidyl ether or epoxides of the epichlorohydrin-substituted bis- or polyphenols type (epoxides having a degree of polymerization of 1 to 2, sold under the name Epikote® E 828 by Shell ), or tetraglycidylmethylenedianiline (eg LY 1802 from Ciba).
- ethylenically unsaturated monomers and polyisocyanates are preferred. Suitable ethylenically unsaturated monomers and polyisocyanates are described above.
- Preferred monoethylenically unsaturated monomers for combination with polyisocyanates are hydroxy-functional ethylenically unsaturated monomers, such as hydroxy-functional C 2 -C 6 -alkyl esters of acrylic acid or methacrylic acid, especially 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate or 3-hydroxypropyl methacrylate.
- ethylenically unsaturated monomers are understood as meaning monomers having exactly one free-radically polymerizable C-C double bond.
- Multiply ethylenically unsaturated monomers are understood as meaning monomers having at least two, preferably two to three, in particular two, radically polymerizable C 1 -C 2 double bonds which are preferably not conjugated.
- Suitable monoethylenically unsaturated monomers are listed above in the description of ethylenically unsaturated monomers.
- Preferred simply ethyle- unsaturated monomers are hydroxy-functional C 2 -C 6 -alkyl esters of acrylic acid or methacrylic acid, and vinylpyrrolidone, especially 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate or 3-hydroxypropyl methacrylate. hydroxypropyl methacrylate.
- Suitable polyethylenically unsaturated monomers are the diesters of diols with acrylic acid or methacrylic acid, furthermore the diallyl and divinyl ethers of these diols. Examples are ethanediol diacrylate, ethylene glycol dimethacrylate, polalkylene glycol di (meth) acrylate, ethylene and / or propylene being mostly used as the alkylene,
- divinylbenzene, trivinylbenzene and divinylcyclohexane and trivinylcyclohexane polyesters of polyols with acrylic acid and / or methacrylic acid, and also the polyallyl and polyvinyl ethers of these polyols.
- Methacrylates trimethylolpropane triacrylate and methacrylate, pentaerythritol triallyl ether, pentaerythritol tetraallyl ether, pentaerythritol triacrylate and pentaerythritol tetraacrylate or the corresponding methacrylates and their technical mixtures.
- Particular preference is given to propanediol, butanediol, pentanediol and hexanediol diacrylate and the corresponding methacrylates.
- Preferred comunications comprising mono and multi-ethylenically unsaturated monomers are 2-hydroxyethyl (meth) acrylate and pentaerythritol triacrylate; 2-hydroxyethyl (meth) acrylate and butanediol di (meth) acrylate; and 2-hydroxyethyl (meth) acrylate and polalkylene glycol di (meth) acrylate.
- Suitable polyisocyanates have been described above.
- Suitable polyols are alcohols having at least two alcohol groups, such as ethanediol, diethylene glycol, 1, 2 or 1, 3-propanediol, dipropylene glycol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, 1 , 10-decanediol, glycerol and trimethylolpropane, and also Dialkoho- Ie containing aromatic or aliphatic ring systems, such as. B.
- polyester polyols from lactones, eg. Caprolactone or hydroxycarboxylic acids, e.g. Hydroxycaproic.
- Polymers having at least two alcohol groups may also be used, such as polyvinyl alcohol or partially hydrolyzed polyvinyl acetate. Mixtures of the aforementioned polyols are also possible.
- Preferred polyhydric alcohols are diethylene glycol, 1, 4-butanediol, 1, 5-pentanediol and 1, 6-hexanediol.
- Comonomers comprising polyisocyanates and polyamines are furthermore preferred as wall monomers.
- Suitable polyisocyanates have been described above.
- polyamines compounds having at least two, preferably two to four, in particular especially two to three amino groups are used.
- Suitable polyamines are preferably aliphatic primary and secondary polyamines.
- Examples which may be mentioned are: 1,2-ethylenediamine, diethylenetriamine, triethylenetetramine, bis (3-amino-propyl) amine, bis (2-methylaminoethyl) methylamine, 1,4-diamino-cyclohexane, 3-amino-methylaminopropane, N- Methyl bis (3-aminopropyl) amine, 1, 4-diamino-n-butane, 1, 6-diamino-n-hexane, polyvinylamine, amino-terminated polyethers.
- Preferred polyamines are 1, 2-ethylenediamine, diethylenetriamine and triethylenetetramine.
- Comonomers comprising polyepoxides and polyamines are furthermore preferred as wall monomers. Suitable polyepoxides and polyamines have been described above.
- the wall monomers are generally employed in a weight ratio of wall monomer to polyester monomer of from 1: 5 to 10: 1, preferably from 1: 3 to 7: 1, more preferably from 1: 1 to 4: 1.
- the process according to the invention for the production of effect-containing microparticles M comprises A) the formation of a crude suspension of microparticles A by means of enzymatic polyester synthesis in an inverse miniemulsion comprising enzyme, effect substance and polyester monomers; and B) the polymerization of wall monomers from the group of ethylenically unsaturated monomers, polyisocyanates and / or polyepoxides in the crude suspension of microparticles A. Steps A) and B) are usually carried out in the order mentioned.
- a crude suspension of microparticles A is formed by enzymatic polyester synthesis in an inverse miniemulsion containing enzyme, effect substance and polyester monomers.
- at least one dispersing agent, at least one nonpolar liquid, at least one polar liquid, at least one polyester monomer, at least one enzyme catalyzing the polymerization and at least one effect substance are combined in any order and an inverse miniemulsion is produced therefrom. It is also possible to prepare premixes of individual components.
- at least one enzyme catalyzing the polymerization of the polyester monomer is introduced into a previously prepared inverse miniemulsion.
- the process according to the invention preferably takes place in such a way that at least one dispersing agent is introduced into at least one subset of a liquid and a subset of the polyester monomers.
- the effect substance and a partial amount of the polyester monomers are separately introduced into at least a subset of the liquid.
- the two mixtures are combined and made an inverse miniemulsion.
- subsets of the polyester monomers and the enzyme are introduced into the miniemulsion.
- “Subset of polyester monomers” in this context means between 0 to 100% of the total polyester monomers contained in the reaction mixture.
- a portion of the polyester monomers is incorporated into the miniemulsion, the subset being greater than 1%, preferably greater than 10% , such as preservatives, can be incorporated at any process step.
- the process of the invention is generally carried out at a reaction temperature of 5 to 100 0 C, often from 20 to 80 0 C and often from 30 to 65 0 C. In general, the process is carried out at a pressure (absolute values) usually from 0, 8 to 10 bar, preferably from 0.9 to 2 bar and in particular at 1 bar (atmospheric pressure).
- the person skilled in the art directs the reaction time according to the desired properties of the microparticles, for example the degree of polymerization. After the desired reaction time, the enzyme may be destroyed or reused, the microparticles isolated or the reaction mixture otherwise isolated or further processed.
- the crude suspension of microparticles A is preferably used directly for step B).
- a macroemulsion is prepared by introducing energy into the mixture of the phases by shaking, whipping, stirring, turbulent mixing; by injecting one fluid into another; by vibrations and cavitation in the mixture (eg ultrasound); by emulsifying centrifuges; through colloid mills and homogenizers; or by means of a jet nozzle, as described for example in WO 2006/053712.
- the macroemulsion is converted by homogenization into a miniemulsion with droplet sizes below 1000 nm.
- the homogenization is preferably carried out at 0 to 100 0 C by using ultrasound, high-pressure homogenizers or other high-energy homogenization, such as jet nozzles.
- solid microparticles of the polyester monomers form during the reaction time in the inverse miniemulsion catalysed by the enzyme.
- the formation of solid microparticles produces a crude suspension of microparticles A from the inversion miniemulsion A.
- step B the polymerization of wall monomers from the group of ethylenically unsaturated monomers, polyisocyanates and / or polyepoxides in the crude suspension of microparticles A.
- at least one wall monomer is introduced into a previously prepared crude suspension of microparticles A and then polymerized. More preferably, at least one wall monomer and at least one dispersant are added to the crude suspension.
- the polymerization of the wall monomers can be carried out by conventional means, such as by polymerization. Catalysts or physical methods. If the wall monomers comprise ethylenically unsaturated monomers, radical initiators are usually added as polymerization catalysts and / or the reaction temperature is increased. If the wall monomer comprises polyisocyanates, then the aforementioned polyurethane catalysts are usually added as polymerization catalysts.
- step B) takes place in such a way that the crude suspension from step A) is admixed with at least one dispersant and at least one wall monomer.
- the crude suspension is preferably admixed with an emulsion comprising wall monomer and dispersant.
- an emulsion of wall monomers in the crude suspension of microparticles A preferably forms.
- at least one polymerization catalyst is added.
- Wall monomer, dispersant and polymerization catalyst may be added in an amount, in multiple aliquots or continuously.
- Wall monomer, dispersant and polymerization catalyst can be dissolved or dispersed in polar or non-polar solvent before being added to the crude suspension.
- At least one wall monomer is already added in step A) and is polymerized only during step B). Preference is given to using wall monomers which do not carry any primary or secondary hydroxyl groups. In particular, ethylenically unsaturated monomers which do not carry primary or secondary hydroxy groups are suitable.
- the process of the invention is generally carried out at a reaction temperature of 20 to 120 0 C, often from 40 to 90 0 C and often from 50 to 80 0 C.
- the process is carried out at a pressure (absolute values) usually from 0, 8 to 10 bar, preferably from 0.9 to 2 bar and in particular at 1 bar (atmospheric pressure).
- the person skilled in the art directs the reaction time according to the desired properties of the microparticles, for example the degree of polymerization.
- the reaction mixture is usually mixed, for example by continuous stirring.
- step B) the effect-containing microparticles M form from the microparticles A and the polymerized wall monomers.
- small proportions, preferably less than 20% by weight, in particular less than 5% by weight, based on the total amount of all microparticles, of non-inventive microparticles can additionally be formed only from the polymerized wall monomers.
- This secondary nucleation is a common side reaction that can be reduced by the skilled person by conventional means, for example by slow metering of the wall monomers, or low concentration of the wall monomers in the continuous phase.
- microparticles M are possible without further workup. After the preparation of the microparticles according to the invention, they can be used as needed be isolated, that is to be freed from solvents. Suitable methods are, for example, evaporation, spray drying, freeze drying, centrifugation, filtration or vacuum drying. In a preferred embodiment, the microparticles are not isolated after preparation.
- microparticles M can be converted into dispersions of the invention by dispersing the microparticles in water or aqueous solutions, for example by phase transfer methods, flush-analogous transfer methods, or preferably by drying the particles to a powder which is subsequently re-dispersed.
- the dispersion prepared according to the invention containing microparticles M or the further processed product can be used as a component in colorants, cosmetics, pharmaceuticals, crop protection agents, fertilizers, additives for food or animal feed, auxiliaries for polymers, paper, textile, leather, paints or detergents and cleaners , It is advantageous that the effect material can be selectively released again, especially in the biosphere, where polyester-degrading enzymes are ubiquitous.
- the present invention relates to an agrochemical formulation comprising microparticles M according to the invention or microparticles M prepared according to the invention.
- formulation auxiliaries in the context of the invention are auxiliaries which are suitable for the formulation of agrochemical active substances, such as solvents, carriers, surfactants (ionic or nonionic surfactants, adjuvants, dispersants), Preservatives, defoamers and / or antifreeze agents
- seed treatment auxiliaries may optionally also be dyes, binders, gelling agents and / or thickeners.
- the agrochemical formulations may comprise 0 to 90% by weight, preferably 1 to 85% by weight, more preferably 5 to 80% by weight, and especially 5 to 65% by weight of formulation aid.
- the present invention relates to methods for controlling undesired plant growth, wherein the unwanted plants, the soil on which the unwanted plants grow, or their seeds are treated with an agrochemical formulation according to the invention.
- the present invention relates to methods for controlling undesirable insect or mite infestation on plants and / or for controlling phytopathogenic fungi, wherein the fungi / insects, their habitat or to be protected against fungal or insect infestation plants or soils or the plants, the soil on which the plants grow, or their seeds treated with an agrochemical formulation of the invention.
- the present invention relates to methods for treating seed with an agrochemical formulation according to the invention and seed treated with an agrochemical formulation according to the invention.
- the process according to the invention offers many advantages over conventional processes for producing microparticles: low reaction temperatures and largely neutral pH values allow the use of temperature- and pH-sensitive effect substances;
- the polymers of the microparticle can be prepared directly in situ without consuming expensive storage.
- the microparticles produced according to the invention have advantages: the microparticles are denser than in other preparation processes.
- the microparticles are mechanically more stable than only enzymatically produced microparticles.
- the microparticles may comprise temperature-labile or otherwise sensitive effect substances, they may also comprise dissolved in polar liquid effect substances.
- the rate of release of the effect substance from the microparticles can be controlled by the type and / or amount of the wall monomers. The rate of release is advantageously slower due to the polymerization of the wall monomers compared to particles constructed solely of polyester.
- Partially hydrogenated petroleum distillate partially hydrogenated mineral oil distillate having a boiling point 260-280 0 C, for example as Isopar ® V commercially available from Exxon Mobil Chemical..
- Enzyme a Candida antarctica type B lipase immobilized on spherical polymer beads, for example commercially available as Novozym® 435 from Novozymes, Denmark.
- Dispersant polyester-polyethylene oxide-polyester block copolymer with a
- Caprolactone ⁇ -caprolactone with purity> 99%.
- HEMA 2-hydroxyethyl methacrylate, commercially available from BASF SE.
- AIBN azobisisobutyronitrile
- DBTL dibutyltin dilaurate Isocyanate A: 4,4'-diphenylmethane diisocyanate oligomer having an NCO content of 31.8 g / 100 g (ASTM D 5155-96 A), acidity 150 mg / kg (as HCl, ASTM, D 1638-74) and viscosity of 210 mPaS (DIN 53018), for example commercially available as Lupranat® M20S from BASF SE.
- the effect substance used was a fungicidal pesticide, for example triticonazole.
- a colorant for example, Basacid ® Blue 756 (CI.
- Basacid® Blue 9 triphenylmethane dye, for example, available from BASF SE
- Basacid® Blue 756 is insoluble in Isopar ® V, while it dissolves in propylene carbonate and caprolactone.
- propylene carbonate was used as effect substance.
- the dye Sudan® Blue anthraquinone dye, Cl. Solvent Blue 79, available, for example, from BASF SE
- Sudan® Blue anthraquinone dye, Cl. Solvent Blue 79, available, for example, from BASF SE. It dissolves only in very hydrophobic media, such as Isopar ® V and polycaprolactone. However, it is slightly soluble in water or propylene carbonate.
- Example 2 Polymerization with 300% Hydroxyethyl Methacrylate (HEMA) First, the crude suspension of microparticles was prepared as described in Example 1. Then 3.6 g of dispersant were added and 15 min. touched. After complete dissolution of the dispersant in the oil phase, 18.0 g HEMA was added and stirred for a further 30 min. The polymerization reaction was then started by adding a mixture of 72 g of isopar V and 0.36 g of AIBN. To ensure complete conversion, the same amount of AIBN in 24 g of isopar V was added again after a reaction time of 6 h at 60 0 C and further polymerized until complete conversion.
- HEMA Hydroxyethyl Methacrylate
- Example 2 To prepare an SEM (scanning electron microscope) image, the product obtained was centrifuged as in Example 1, the solid thus obtained was washed with isobutanol and hexane and dried in air. The dried solid was then finely crushed in a mortar to a powder. The SEM image showed intact, spherical microparticles (FIG. 3). To further control the stability of the particles, the powder was redispersed in a 1% strength by weight aqueous SDS solution by means of ultrasound (1 min, with ice cooling, 100% with sonotrode H7). Photomicrographs (1000x magnification) showed intact spherical particles.
- the experiments show the high mechanical stability, in particular in comparison to the particles from Example 1.
- Example 3 Polymerization with 200% Hydroxyethyl Methacrylate
- the crude suspension of microparticles was prepared as described in Example 1. Then 2.4 g of dispersant was added and 15 min. touched. After complete dissolution of the dispersant in the oil phase, 12.0 g of HEMA were added and the mixture was stirred for a further 30 min.
- the polymerization reaction was then started by adding a mixture of 24 g of partially hydrogenated mineral oil distillate and 0.24 g of AIBN. In order to ensure a complete conversion, the same amount of AIBN in 24 g of partially hydrogenated mineral oil distillate was added again after a reaction time of 6 h at 60 0 C and further polymerized until complete conversion. To prepare for SEM uptake, the product obtained was as in
- Example 2 prepared. The SEM image showed intact, spherical microparticles.
- the crude suspension of microparticles was prepared as described in Example 1. Then, 1, 2 g of dispersant were added and 15 min. touched. After complete dissolution of the dispersant in the oil phase 6.0 g HEMA was added and stirred for a further 30 min. The polymerization reaction was then started by adding a mixture of 24 g of partially hydrogenated mineral oil distillate and 0.12 g of AIBN. After a reaction time of 6 h at 60 ° C., the addition of 6.0 g of HEMA was carried out and, after a further 20 h, the addition of a further 6.0 g of HEMA, in each case in conjunction with an addition of 1.2 g of dispersant and 0.12 g AIBN in 24 g IsoparV. After the last HEMA addition was at 60 0 C until complete conversion 12 h further polymerized. To prepare for SEM uptake, the product obtained was prepared as in Example 2. The SEM image showed intact, spherical microparticles.
- Example 5 Particles Without Propylene Carbonate, Polymerization With 300% HEMA The following quantities were used to prepare the inverse miniemulsion: 114.0 g portion hydrogenated mineral oil distillate 30.0 g ⁇ -caprolactone 96 mg D-sorbitol 0.82 g triticonazole 6.0 g Dispersant 3.0 g Novozym 435
- the dispersant was placed in a sample vessel and dissolved with stirring in partially hydrogenated mineral oil distillate.
- triticonazole was dissolved in a mixture of caprolactone and sorbitol.
- the homogeneous solutions were then mixed together and pre-emulsified by stirring with the magnetic stirrer (60 min at room temperature).
- ultrasound ultrasound processor UP 400S from Hielscher
- an inverse miniemulsion was prepared therefrom while cooling with an ice bath (5 min, 100% with sonotrode H7) and polymerized at 60 ° C. for 48 h after addition of the enzyme.
- Example 2 To prepare for SEM uptake, the product obtained was prepared as in Example 2. The SEM image showed intact, spherical microparticles.
- Example 7 Polymerization with HEMA and Isocyanate A - NCO / OH Ratio
- OH groups of HEMA are crosslinked with isocyanate A at different ratios of OH to NCO.
- 30.0 g of the end product obtained in Example 2) were admixed with isocyanate A and heated to 60 ° C. with stirring with a magnetic stirrer. After addition of 0.01 g of DBTL as catalyst, the reaction mixture was stirred overnight to complete NCO conversion.
- the product obtained was prepared in each case as in Example 2.
- the SEM image showed intact, spherical microparticles.
Abstract
Description
Claims
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DE102012200077A1 (de) * | 2012-01-04 | 2013-07-18 | Cortronik GmbH | Ballonkatheter mit einer aktiven Beschichtung |
AU2013229954B2 (en) | 2012-03-09 | 2016-12-15 | Kraft Foods Group Brands Llc | Food and beverage products containing 1,3-propanediol and methods of modifying flavor release using 1,3-propanediol |
AU2013230765B2 (en) | 2012-03-09 | 2016-02-04 | Kraft Foods Group Brands Llc | Oxidized flavor note suppression in comestibles |
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US10049349B1 (en) | 2015-09-29 | 2018-08-14 | Square, Inc. | Processing electronic payment transactions in offline-mode |
CN113164897A (zh) * | 2018-10-30 | 2021-07-23 | 巴斯夫欧洲公司 | 制备被活性材料填充的微粒的方法 |
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2009
- 2009-10-14 BR BRPI0919589A patent/BRPI0919589A2/pt not_active IP Right Cessation
- 2009-10-14 JP JP2011532593A patent/JP2012508090A/ja active Pending
- 2009-10-14 US US13/125,388 patent/US20110230343A1/en not_active Abandoned
- 2009-10-14 EP EP09821620A patent/EP2352580A1/de not_active Withdrawn
- 2009-10-14 CN CN2009801521770A patent/CN102264464A/zh active Pending
- 2009-10-14 WO PCT/EP2009/063379 patent/WO2010046286A1/de active Application Filing
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Also Published As
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WO2010046286A1 (de) | 2010-04-29 |
JP2012508090A (ja) | 2012-04-05 |
BRPI0919589A2 (pt) | 2015-12-08 |
CN102264464A (zh) | 2011-11-30 |
US20110230343A1 (en) | 2011-09-22 |
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