CN101141877A - 配制品 - Google Patents
配制品 Download PDFInfo
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- CN101141877A CN101141877A CNA2006800085179A CN200680008517A CN101141877A CN 101141877 A CN101141877 A CN 101141877A CN A2006800085179 A CNA2006800085179 A CN A2006800085179A CN 200680008517 A CN200680008517 A CN 200680008517A CN 101141877 A CN101141877 A CN 101141877A
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- liquid
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- 239000000203 mixture Substances 0.000 title description 18
- 238000009472 formulation Methods 0.000 title description 4
- 239000007788 liquid Substances 0.000 claims abstract description 143
- 239000006185 dispersion Substances 0.000 claims abstract description 90
- 239000002270 dispersing agent Substances 0.000 claims abstract description 53
- 239000002245 particle Substances 0.000 claims abstract description 51
- 239000007787 solid Substances 0.000 claims abstract description 33
- 239000012634 fragment Substances 0.000 claims description 55
- 239000003905 agrochemical Substances 0.000 claims description 14
- 238000004132 cross linking Methods 0.000 abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 239000012071 phase Substances 0.000 description 55
- 238000005189 flocculation Methods 0.000 description 42
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- 229920000642 polymer Polymers 0.000 description 28
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 25
- 238000002360 preparation method Methods 0.000 description 23
- -1 proproanmide Chemical compound 0.000 description 23
- 239000000178 monomer Substances 0.000 description 17
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- 238000000034 method Methods 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 13
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 12
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- 239000000243 solution Substances 0.000 description 11
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- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
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- 230000000694 effects Effects 0.000 description 7
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- 125000000524 functional group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
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- 150000003335 secondary amines Chemical class 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 150000001541 aziridines Chemical class 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
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- 230000000361 pesticidal effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 150000002466 imines Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000003795 desorption Methods 0.000 description 3
- 150000001261 hydroxy acids Chemical group 0.000 description 3
- 125000004425 isosulfocyanate group Chemical group 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000005784 Fluoxastrobin Substances 0.000 description 2
- 239000005800 Kresoxim-methyl Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical group [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 239000005938 Teflubenzuron Substances 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 description 2
- 229960002587 amitraz Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000007860 aryl ester derivatives Chemical class 0.000 description 2
- RQVGAIADHNPSME-UHFFFAOYSA-N azinphos-ethyl Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OCC)OCC)N=NC2=C1 RQVGAIADHNPSME-UHFFFAOYSA-N 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- KXRPCFINVWWFHQ-UHFFFAOYSA-N cadusafos Chemical compound CCC(C)SP(=O)(OCC)SC(C)CC KXRPCFINVWWFHQ-UHFFFAOYSA-N 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000012711 chain transfer polymerization Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Chemical class 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 230000008029 eradication Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- UFEODZBUAFNAEU-NLRVBDNBSA-N fluoxastrobin Chemical compound C=1C=CC=C(OC=2C(=C(OC=3C(=CC=CC=3)Cl)N=CN=2)F)C=1C(=N/OC)\C1=NOCCO1 UFEODZBUAFNAEU-NLRVBDNBSA-N 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
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- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical group CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- IWVKTOUOPHGZRX-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.COC(=O)C(C)=C IWVKTOUOPHGZRX-UHFFFAOYSA-N 0.000 description 2
- JHIPUJPTQJYEQK-ZLHHXESBSA-N orysastrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1CO\N=C(/C)\C(=N\OC)\C(\C)=N\OC JHIPUJPTQJYEQK-ZLHHXESBSA-N 0.000 description 2
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- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 2
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- 239000000725 suspension Substances 0.000 description 2
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
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- 229920003176 water-insoluble polymer Polymers 0.000 description 2
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- ZCVAOQKBXKSDMS-PVAVHDDUSA-N (+)-trans-(S)-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-PVAVHDDUSA-N 0.000 description 1
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 description 1
- IPPAUTOBDWNELX-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group C1=C([N+]([O-])=O)C(C(=O)OCC(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 IPPAUTOBDWNELX-UHFFFAOYSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 description 1
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 1
- IQVNEKKDSLOHHK-FNCQTZNRSA-N (E,E)-hydramethylnon Chemical compound N1CC(C)(C)CNC1=NN=C(/C=C/C=1C=CC(=CC=1)C(F)(F)F)\C=C\C1=CC=C(C(F)(F)F)C=C1 IQVNEKKDSLOHHK-FNCQTZNRSA-N 0.000 description 1
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- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 1
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
- INARFNQOWWSXLS-UHFFFAOYSA-N 1-amino-2-methylpropane-1-sulfonic acid Chemical compound CC(C)C(N)S(O)(=O)=O INARFNQOWWSXLS-UHFFFAOYSA-N 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-UHFFFAOYSA-N 0.000 description 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 1
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 1
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- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-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
- ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 1
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- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
- C05G5/00—Fertilisers characterised by their form
- C05G5/20—Liquid fertilisers
- C05G5/27—Dispersions, e.g. suspensions or emulsions
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract
一种在液体连续相中含固体颗粒或液滴的不连续相的分散液;一种具有在连续相可溶的片段和在连续相中不可溶的片段的聚合分散剂;及通过交联聚合分散剂形成的围绕不连续相的固体颗粒或液滴网状结构;其中交联发生于连续相中的可溶片段之间。
Description
本发明涉及颗粒分散液和乳液,特别涉及活性的聚合分散剂稳定颗粒分散液和乳液的用途。
颗粒分散液和乳液广泛用于多种应用上,耗费了相当大的努力来生产在使用中获得期望效果的稳定配制品。颗粒分散液和乳液通常是通过在分散相和连续相的界面上是物理上可吸附的表面活性剂或表面活化剂稳定,以便维持离散的分散体的分离。然而,这样的物理上吸附的表面活性剂由于其他表面活性化合物或应激配制品的条件例如,温度周期性变化或电解质浓度,通过竞争性地脱附作用移位。存在研发改善分散系统的配制品的鲁棒性的选择和手段所需的常量。
在制备强的配制品中遭遇的问题的进一步的实例涉及分散相中颗粒的大小和形状的增加。某些化学上的化合物(尤其是农业化学药品)可能是轻微地溶于连续相的液体介质中。这可能导致产生分散相的新晶体或分散相的原始晶体的生长。这些事件可能产生这样的晶体,其大小和形状对配制品的使用是有害的。由于存在不吸附于分散相和连续相的界面的表面活性剂,可以运送进入和穿过液体连续相的分散相的物质的量已知是增加的。此过程已知为Ostwald ripening;在乳液中除了导致结晶,其还导致液滴尺寸的增加。
US 62621 52、WO 02/100525和WO 2004/052099[其各自内容在此引入作为参考]公开了,某些分散液或乳液的配制品鲁棒性可以通过吸附在分散于连续相中的液滴或固体颗粒上的化学交联的聚合分散剂分子增强。这些公开使用了两亲聚合物,其是通过存在于聚合物片段上的功能基团交联的,所述聚合物片段在连续相中是不溶的。
本发明提供了增强乳液和颗粒分散液鲁棒性的选择性手段,通过在液/液或固/液界面不可逆地混入聚合分散剂,以便该吸附剂不能解吸附。令人吃惊地,我们已经发现,这样的聚合分散剂可以是通过存在于聚合物片段上的官能团交联的,所述聚合物片段在连续相中是可溶的。
因此,本发明提供了一种在液体连续相中含固体颗粒或液滴的不连续相的分散液;具有在连续相可溶的片段和在连续相中不可溶的片段的聚合分散剂;及通过交联聚合分散剂形成的围绕不连续相的固体颗粒或液滴网状结构;其中交联发生于连续相中的可溶片段之间。
适宜地,本发明的固体颗粒或液滴具有1000-0.1μm的平均直径,更适合地是100-0.5μm,甚至更适合地是5.0-1.0μm。
术语“固体颗粒”包括微粒体,其可能具有贮库(reservoir)或基质结构。基质结构是“固体颗粒”。贮库结构具有中空内部的固体外壳,通常在内部含有液体。
适合地,本发明的分散液是这样的,其中连续相是水性基的;术语“水性基”是指含有超过50%水重量的连续相。农药配制品在水性基的连续相中可以含有机溶剂。例如,丙二醇可以加入,作为防冻剂。
在某些情形下,优选的是连续相是非水性基的。
分散的物质的性质对于本发明的保护范围不是关键的,可以使用任何适于作为分散相的固体或液体。然而,本发明的优点可能是与特定分散相物质及应用的特定关联性。例如,本发明的分散液在需要不同分散物质混合物的配制品中将是特别有用的,或者对于抗聚集、团聚或聚结的长期稳定性存在问题是特别有用的。
关于本发明的乳液,分散相的液滴将包含一种与连续相的液体不混溶的液体,其可以包含进一步的组分。进一步的组分可能是液体,其可能是溶解于分散相的液体中的固体或其可能是作为颗粒分散于分散相的液体中的固体。
本发明可用于大量的商业产品,包括但不限于农药配制品、生物活性化合物,涂料类[如涂料类和漆类]、颜料类[如墨水类、染料类和色素类]、化妆品类[如口红类、foundations、亮甲剂类(nail polishes)和遮光剂类]、调味料类、芳香剂类、磁性和光学记录介质[如磁带和磁盘]及药品。
本发明的分散液可以是具有含农药的固体颗粒或含农药的液滴的农药分散液,在这样情况下,分散相可以包含杀菌剂、肥料或植物生长调节剂,或特别是杀真菌剂、除草剂或杀虫剂。
因此,在适合的方面,本发明的分散液是农药分散液。
农药分散液不是必含农药活性成分,其可以简单地包含连同农药活性成分使用的辅剂。在其他作用之中,辅剂可以是生物学上有效的,提高耐雨性、降低光降解或改变土壤迁移。
此外,在同一连续相中可以存在分散的固体颗粒和液滴,其中固体颗粒可以包含一种农药活性成分,同时液滴包含另一种农药活性成分。这种配制品的实例是水性基的悬乳剂(suspoemulsion)。是本发明特别有利的,在悬乳剂中可使用相同的聚合分散剂来稳定固体颗粒和液滴,以对抗聚集、絮凝、团聚或卷吸(engulfment),即使在一个实例中其是交联的而在另一个其不是交联的。例如,其可以是,固体颗粒上的聚合分散剂是交联的但是液滴上的聚合分散剂不是交联的或者反之亦然。使用相同的聚合分散剂可以避免不相容的问题。同样地,采用相同的聚合分散剂具有不止一种类型的分散于连续相中的固体颗粒[或液滴]是有可能的,以便避免不相容的问题。
对于不同物质的固体颗粒和/或油滴的混合物的本发明的保护范围不限于其中所有分散体是用本发明的聚合分散剂稳定的实施例。例如,根据本发明制得的分散液可另外地包含使用常规表面活性剂或分散剂分散的固体颗粒或液滴。技术人员将知道用于此目的的适合常规表面活性剂或分散剂。
可作为固体颗粒分散于或溶解于与水不混溶的有机溶剂的或者溶解于与水不混溶的有机溶剂的任何农业化学药品是可以用于本发明。
适合的农业化学药品的实例包括但不限于:
(a)除草剂如二氢吡啶、硝草酮、氟磺胺草醚、肟草酮、草萘胺、阿米曲士、敌稗、cyprodanil、嘧霉胺、氯硝胺、四氯硝基苯、托壳勒福斯甲基(toclofos methyl)、环糊精M、2,4-D、MCPA、2-甲-4氯丙酸、炔草酸酯(clodinafop-propargyl)、cyhalofop-butyl、禾草灵、氟吡甲禾灵、精喹禾灵、吲哚-3-基乙酸、1-萘乙酸、异草胺、牧草胺、二甲基敌草索、苯菌灵、呋草黄(benfuresate)、二氯甲氧苯酸、敌草腈、草除灵、唑菌嗪、氟佐隆、伏虫隆(teflubenzuron)、甜菜宁、乙草胺、甲草胺、异丙甲草胺、丙草胺、thenylchlor、禾草灭、丁苯草酮、烯草酮、cyclodim、赛速氧啶(sethoxydim)、得杀草、二甲戊乐灵、特乐酚、必芬诺、乙氧氟草醚、三氟羧草醚、乙羧氟草醚、溴草腈、4-羟(基)-3,5-二碘苯甲腈、咪草酸、依灭草、灭草喹、咪草烟、甲咪唑烟酸、甲氧咪草烟、丙炔氟草胺、氟烯草酸、落叶素、amodosulfuron、氯磺隆、烟嘧磺隆、砜嘧磺隆、醚苯磺隆、野麦畏、丁乙硫代氨甲酸丙酯、苄草丹、禾草特、阿特拉津、西玛津、草净津、莠灭净、扑草净、草净津(terbuthylazine)、去草净、磺草酮、异丙隆、利谷隆、非草隆、绿麦隆和甲氧隆;
(b)杀真菌剂如嘧菌酯(azoxystrobin)、肟均酯(trifloxystrobin)、醚均酯(kresoxim methyl)、唑菌酮(famoxadone)、苯氧菌胺、啶氧菌酯、苯咪氨甲酯、噻苯咪唑、达灭芬、免克宁、依普同、二硫代氨基甲酸盐、伊米萨利、扑克拉、氟喹唑、氟环唑、氟三唑、氮康唑、比多农、溴克座(bromuconazole)、环唑醇、待克利、菲克利、巴克素(paclobutrazol)、丙环唑、得克利、三唑酮、灭菌唑、芬普福、二甲十三烷吗啉、苯锈啶、代森锰锌、代森联、四氯二氰苯、塞仑、福美锌、敌菌丹、克菌丹、灭菌丹、三氟拉嗪、氟纹胺、萎锈灵、甲霜灵、乙嘧酚磺酸酯、乙菌定、醚菌胺、氟嘧菌酯、肟醚菌胺(orysastrobin)、苯氧菌胺、丙硫菌唑、8-(2,6-二乙基-4-甲基-苯基)四氢吡唑并[1,2-d][1,4,5]二氮杂-7,9-二酮和2,2,-二甲基-丙酸-8-(2,6-二乙基-4-甲基-苯基)-9-氧-1,2,4,5-四氢-9H-吡唑并[1,2-d][1,4,5]-二氮杂-7-基酯;和
(c)杀虫剂如阿巴美丁、高灭磷、啶虫脒、氟丙菊酯、棉铃威、丁醛肟威、丙烯除虫菊素、α-氯氰菊酯、阿米曲士、磺草灵、川楝素、甲基吡磷、乙基谷硫磷、谷硫磷、虫威、丙硫克百威(benfuracarb)、bensultap、β-氟氯氰菊酯、β-氯氰菊酯、毕芬宁、生物烯丙菊酯、除虫菊酯、双三氟虫脲、硼砂、噻嗪酮、丁酮砜威、硫线磷(cadusafos)、西维因、虫螨威、氯普芬、可尼丁、氟氯氰菊酯、三氟氯氰菊酯、赛灭宁(cyprmethrin)、溴氰菊酯、万霉灵、二氟脲、呋虫胺、甲氨基阿维菌素(emamectin)、硫丹、芬诺克、倍硫磷、氰戊菊酯、氟虫腈、溴氟醚菌酯、七氯、蚁爱呷(hydramethylnon)、吡虫啉、炔咪菊酯、异丙威、λ三氟氯氰菊酯、甲胺磷、灭虫威、灭多虫、烯啶虫胺、氧乐果、扑灭司林、比加普、甲基嘧啶磷、残杀威、得芬诺、碘硫甲乙铵、硫敌克、杀虫脲和灭杀威。
聚合分散剂或表面活性剂的组合物及制备方法是多种且变化的。这种物质的综述是在Piirma撰写的文件Polymeric Surfactants,Surfactant Science Series 42(Marcel Dekker,New York,1992)中给出。一类重要的聚合分散剂是那些称为“两亲的”或“两性分子的”,其可以是具有连接于聚合主链的伸出的聚合物臂的栉状的共聚物,或嵌段共聚物。聚合分散剂的表面活化性质是由化学组合物和不同聚合物片段的相对大小决定的。
例如,用于水性系统的嵌段共聚物的表面活性剂可具有毗连水不溶聚合物如聚氧化丙烯的片段的水可溶的聚合物如聚氧化乙烯的片段;同时用于水性系统中的栉状的共聚物的表面活性剂可以具有毗连作为主链的水不溶聚合物如聚甲基丙烯酸甲酯的片段的作为悬臂水溶的聚合物如聚氧化乙烯的片段。
当聚合分散剂具有高倾向于吸附至胶体表面但是在连续相中少许或没有倾向于micellise或另外的聚集,吸附在界面上的聚合物的量达到最大值。
用于本发明的聚合分散剂可具有可溶于连续相单个片段,此片段提供交联的作用以及胶体稳定的作用。选择性地,可有不止一种可溶于连续相的片段,一种这样的片段可提供交联的功能同时另一种片段可提供胶体稳定的作用;在这种聚合分散剂种,交联片段和胶体稳定片段的化学是相同的,但是优选是它们为不同的。
因此,在本发明适合的方面,存在如上述的分散液,其中聚合分散剂具有可溶于连续相的第二片段,且该第二可溶的片段是化学上不同于其他可溶的片段。当化学是不同时,交联可以是通过相对于特定交联片段的化学特别机制获得;即是,可选择化学性质以便不存在这样的机制,通过该机制可存在胶体稳定片段的交联。当交联片段和胶体稳定片段的化学性质是相似时,胶体稳定片段的低水平交联是可接受的,其中这不突变地影响胶体稳定性;特别地,当所得的交联结构增强片段在连续相中的溶剂化时,将是这样的情况。
存在大量的聚合物结构,借此交联的在连续相中可溶的片段可以实现,而不影响胶体稳定。例如,以下的结构是适于和水用作液体连续相。
·毗连栉状的共聚物的水可溶的可交联的聚合物的片段。在栉状的共聚物中,主链是水不溶的且悬臂是水溶的;选择性地,主链是水溶的且悬臂是水不溶的。然后选择交联的机理以便在可交联的聚合物片段上发生而不在水溶的悬臂或水溶的主链。
·毗连水溶的可交联的片段的水溶的片段毗连水不溶的片段。然后选择交联的机理,以便在第一水可溶的片段上不发生,且交联是受限于第二水可溶的片段,邻近水可溶的片段。
·毗连水不可溶的片段的水可溶的片段毗连可交联的水可溶的片段。然后选择交联的机理,以便仅在可交联的水可溶的片段上发生。
·可交联的水可溶的片段毗连水不溶的片段。这可以采用二嵌段共聚物或采用栉状的共聚物获得,其中主链是水不溶的且悬臂是水溶的或选择性地主链是水溶的且悬臂是水不溶的。然后,选择交联的机理以便获得围绕分散相的固体颗粒或液滴的水溶胀水凝胶,其提供了足够的阻碍以防止聚并、团聚、聚集或其他可能导致差的配制品行为的事件。
给出上述实施例的目的是仅用以说明,本领域技术人员将是熟悉其他结构,其可满足通过水可溶的片段交联的标准,同样地将是能够适应对于具有非水性基连续相的分散液的上述教导。
用于本发明的两亲聚合物可以是由多种手段制得,主要是通过以受控的或分步的方式的形成的聚合片段的偶合或单体的聚合作用。例如,用于水性基连续相的嵌段共聚物分散剂可以是通过以下制得,(i)第一水不溶单体和第二水溶单体受控的分步聚合作用,或者此过程的反转;或者(ii)偶合形成的水不溶和水溶的聚合片段在一起。本领域技术人员知道这些手段各自的不同优点和缺陷。
适合地,聚合分散剂是两亲的共聚物,含有多种乙烯基单体,其可以是毗连缩合或开环聚合的产物。
在连续相中可溶的聚合分散剂的片段可包含在连续相中可溶的单体,所述单体是与不溶于连续相的单体共聚,只要总的组合物是这样的以致于片段是溶于连续相。例如,在用于水性基的连续相的聚合分散剂中,可溶于连续相的片段可包含与甲基丙烯酸甲酯共聚的甲基丙烯酸,只要甲基丙烯酸与甲基丙烯酸甲酯的比例是这样的以致于片段在使用的pH下是水溶的。
增强包含其的聚合片段水溶性的乙烯基单体的进一步实例尤其是丙烯酰胺和异丁烯酰胺、丙烯酸和甲基丙烯酸、2-丙烯基氨基-2-甲基丙烷磺酸、2,3-二羟基丙基丙烯酸酯和甲基丙烯酸酯、2-(二甲氨基)乙基丙烯酸酯和甲基丙烯酸酯、亚甲基丁二酸、寡-或聚-乙烯氧化物单-丙烯酸酯或-甲基丙烯酸酯、马来酸、苯乙烯磺酸、甲基丙烯酸磺乙基酯、乙烯吡啶和乙烯基吡咯烷酮。
减少包含其的聚合片段的水溶性的乙烯基单体的实例尤其是丙烯酸甲酯、甲基丙烯酸甲酯及丙烯酸和甲基丙烯酸的其他烷基酯类、丙烯酸苯基酯、甲基丙烯酸苯基酯及丙烯酸和甲基丙烯酸的其他芳基酯类、丁二烯、苯乙烯和烷基取代的苯乙烯类、醋酸乙烯基酯及乙烯基醇的其他烷基或芳基酯类、乙烯基氯化物或偏亚乙烯基二氯化物。
受控的分步聚合反应可以是通过本领域已知的不同方法完成。这些方法通常指的是“天然的”或“受控的”聚合反应,与更多的常规方法相比其对分子量和多分散性指数(加权平均与数均分子量的比例)给予更好的控制。这些方法的实施例可以在科学文献中找到,包括阴离子和阳离子聚合反应,基团转移聚合反应,其需要苛刻的反应条件及非常纯的反应试剂,而天然的自由基聚合反应通常需要要求不高的条件。
已知天然的自由基聚合反应的多种方法。这些包括使用二硫化物或四苯乙烷“引发-转移-终止剂”、一氧化二氮链转移剂、钴复合物链转移剂、使用过渡金属复合物的原子转移基聚合反应及使用含硫有机化合物的基加成-断裂转移聚合反应。
栉状共聚物不需要通过受控的分步反应制得,只要主链是单个的共聚合片段;如果不止一个片段,那么其可以是根据上述关于嵌段共聚物的方法制得。栉状共聚物可以是通过以下制得:(i)主链片段上的悬臂片段的接枝聚合;(ii)预制的悬臂片段与主链片段的结合;或(iii)完成适于主链片段的单体与大分子单体的统计上的或随机的共聚合反应,其与一末端基团上适合的可聚合部分预制的悬臂片段。适于和水溶性的悬臂制备栉状共聚物的大分子单体的实例是单-甲氧基-聚乙二醇-单-甲基丙烯酸酯。
用于任何给定组合物的优选的准备方法将取决于反应试剂的性能和性质。例如,某些单体之间的反应比可能限制可获得的共聚合结构的范围。聚合分散剂的分子量也是重要的因素。如果分子量太大,聚合物在溶液中将是非常粘稠,且难于使用,如果分子量太小,其将不具有同质的化学上的组合物,如果其太广泛地分布,将是难于预测其行为。本领域技术人员能够选择适合的材料和条件以制备期望的适合分子量的共聚物结构。
用于本发明的聚合分散剂是两亲的表面活性分子,其完全吸附在不混溶物质的界面上。交联之前,其用于适于制备期望的分散液的过程中。例如,固体颗粒或不混溶的液体可以是分散入液体连续相,使用胶体或立式球磨、三辊磨、高速转子-定子装置或高压匀浆器。本领域技术人员可以容易地选择适合的方法用于制备期望的分散液,并用于获得期望大小的固体颗粒或液滴。
同时,交联可以具有轻微增加分散液中全部颗粒或液滴大小的作用,如果其完全存在,这种效果通常是微弱的。令人吃惊地,我们已发现甚至交联之后,分散液中的平均颗粒或液滴大小一般很好保持在优选的极限之内,例如,低于约10微米,更特别是低于约5微米。
交联之前,聚合分散剂[A]与混悬的固体或油滴[B]的重量比例(A∶B)适宜是1份A比400份B(1∶400)至1份A比5份B(1∶5),例如1份A比200份B(1∶200)至1份A比10份B(1∶10)。更适合的范围是1∶10至1∶100,例如1∶20至1∶75。特别适合的比例是约1∶50。
在配制品中使用最少需要量的聚合分散剂时,有一明确的益处。此外,发现使用最少需要量的可能使聚合分散剂的无效果的和潜在有害的交联降到最低,通过在水相体内交联片段的反应,与在颗粒和微滴的表面上相对比。
根据本发明,某些反应部分位于溶于液体连续相的聚合片段形式的聚合分散剂内,是交联至在固体颗粒或油滴与连续相的界面上不可逆地结合聚合分散剂。这可能包括反应部分与交联物质的反应,所述交联物质是在制备分散液之前或之后加入连续相。在乳液的情形下,交联物质可以是在制备乳液之前加入不连续的液相中。反应部分还可以彼此反应或者与包含在聚合分散剂的片段之内的不同官能团反应,所述聚合分散剂溶于连续相。任何上述的交联反应可以是自发地产生,或者是受分散液环境的变化触发,该变化如但不限于pH或温度上的变化。应选择适合的反应部分和交联物质以确保过早的交联或副反应如水解,在完成分散液的制备之前减少到最低,而且本领域技术人员应易于能够这样做。
交联反应可以是任何温和的化学反应,其在位于可溶于液体连续相的片段形式的聚合分散剂内的反应部分之间产生有利的结合,这种结合是共价结合或非共价结合。适合的反应这样的,其不需要如高温的条件,高温对于分散液的胶体稳定性或分散液的任何组分的化学稳定性证明是有害的。在使用交联物质的情况下,该物质必须清楚地具有至少两个反应基团的官能度,但可以具有更多。适于聚合分散剂或交联物质中反应部分的官能团的实例是可与醛类或酮类反应的伯胺;可与乙酰乙酸基、酸酐类、氮杂环丙烷类、羧酸类、羧酸卤化物类、环氧化物类、亚胺类、异氰酸酯类、异硫氰酸酯类、N-羟甲基及乙烯基反应的伯胺或仲胺;可与烷基或芳基卤化物反应的伯胺、仲胺或叔胺;可与酸酐类、氮杂环丙烷类、羧酸类、羧酸卤化物类、环氧化物类、亚胺类、异氰酸酯类、异硫氰酸酯类或N-羟甲基反应的羟基;可经历与不稳定酯类的酯交换反应的羟基;可与乙酰乙酸基、酸酐类、氮杂环丙烷类、羧酸类、环氧化物类、亚胺类、异氰酸酯类、异硫氰酸酯和N-羟甲基反应的或可以是还原成二硫化物的巯基;可与伯胺或仲胺、氮杂环丙烷类、碳二亚胺类、环氧化物类、羟基、亚胺类、异氰酸酯类、异硫氰酸酯类、N-羟甲基和巯基反应的羧酸类;可与伯胺或仲胺、羟基、N-羟甲基和巯基反应的羧酸卤化物类或酸酐类;在水存在下可与自身反应的基于硅的基团如硅氧烷;可与伯胺或仲胺或肼类反应的醛或酮基;或可与伯胺或仲胺或自由基反应的乙烯基。
可用于交联的非共价结合的实例包括使用二价或三价金属离子如钙、镁或铝与羧酸基团;过渡金属如铜、银、镍或铁与适合的配基;或者强的氢键结合如硼酸与羟基、双胍类与羧酸或如发生在蛋白质之间的多氢键结合。
对于某些反应,催化剂可用于提高交联发生时的速度。可使用的催化剂的实例是加速胺与羧酸反应的N-羟基琥珀酰亚胺,加速羟基和羧酸反应的的碳二亚胺类,加速环氧化物反应的酸性条件或加速异氰酸酯反应的季胺。考虑到用于交联聚合分散剂的化学,先前的实施例不是限制本发明的保护范围。仅有的条件是经历交联反应的官能团是位于可溶于分散液的液体连续相的聚合物片段上。
适合地,存在于可溶于液体连续相的聚合分散剂的片段上的交联官能团是羧酸,且其是通过具有2个或多个氮杂环丙烷官能团的交联物质交联。通过以下非限制性的实施例说明本发明。
实施例
以下实施例说明了适于制备农药的水分散液的两亲的聚合分散剂的制备,并且该聚合分散剂可以是通过位于水溶性聚合物片段上官能团交联的。
使用的原料及下表中给出的缩写是:丙烯酸正丁基酯[BA](来自Sigma-Aldrich)、2,3-二羟基丙基甲基丙烯酸酯[DHPMA](来自RohmGMBH)、2-(二甲氨基)乙基甲基丙烯酸酯[DMAEMA](来自Sigma-Aldrich)、甲基丙烯酸[MAA](来自Sigma-Aldrich)、丙烯酸甲酯[MA](来自Sigma-Aldrich)、甲基丙烯酸甲酯[MMA](来自Sigma-Aldrich)、N-羟基琥铂酰亚胺基甲基丙烯酸酯[NHSMA](根据Batz等人.in Angew.Chem.Int.Ed.1972,11,1103中的方法制得)、单-甲氧基聚(乙烯二醇)单-甲基丙烯酸酯(分子量大约是1000g/mol[PEGMA1]或2000g/mol[PEGMA2],由Degussa,UK分别以BISOMERTM S10W和S20W销售,且冻干除去水)。所有量是以重量份给出,除非另有说明。
实施例A1-A22
这些聚合分散剂是通过Haddleton等人的(Macromolecules,1997,30,2190-2193)的原子转移基聚合反应制得。分离的聚合物片段是通过连续的(共)单体加成构建;所用的(共)单体批次的组合物在下表1给出。
原子转移基聚合反应的引发剂是作为第一批的部分加入,并记录在表1中。所用的引发剂是乙基-2-溴-异-丁酯[E2BiB](来自Sigma-Aldrich),聚(乙烯二醇)衍生的大-引发剂[PEG-Br],分子量为大约2000g/mole,根据Jankova等人(Macromolecules,1998,31,538-541)的方法制得,或是根据以下过程制得的双酚衍生的二溴化物[BPDB]。
二-2-溴-2-甲基丙酸4.4′-异亚丙基二苯基酯的制备
向8.7份甲苯中含1份4,4′-异亚丙基二酚的浆液喷射干燥的氮气1小时除去氧气。向浆液中加入1.06份三乙胺得到澄清的溶液。反应混合物冷却至0℃,之后在90分钟内滴加2.4份2-溴异丁酰基溴化物,然后在20℃下搅拌混合物24小时。过滤除去得到的沉淀,剩下的浅棕色溶液在真空下浓缩得到棕色固体,其在甲醇中重结晶获得白色絮片的产物。
聚合反应完成之后,用本领域的常规方法分离聚合物。在A1-A15的情况下,溶液穿过活性碱性氧化铝的柱子以除去铜盐,沉淀分离进入石油醚(60-80℃)。在A16-A18的情况下,聚合物溶液用氢氧化铝水溶液(相对于NHSMA单体为1.2摩尔当量)处理以脱保护羧酸基团,在-79℃下沉淀分离聚合物进入丙酮。在A19-A22的情况下,聚合物溶液是通过活性碱性氧化铝的柱子以除去铜盐,在真空下除去溶剂。聚合物随后在pH10(加入NaOH)下溶解于水,在20℃下搅拌24小时以脱保护羧酸基团。
表1
实施例 | 引发剂 | 批次1 | 批次2 | 溶剂 |
A1 | E2BiB 0.3份 | PEGMA1 17.0份MMA 11.4份 | DMAEMA 4.2份 | 甲苯67份 |
A2 | E2BiB 0.3份 | PEGMA1 184份MMA 11.8份 | DMAEMA 2.5份 | 甲苯67份 |
A3 | E2BiB 0.3份 | PEGMA1 17.3份MMA 12.8份 | DHPMA 2.6份 | 甲苯67份 |
A4 | PEG-Br 10份 | DMAEMA 7.9份 | MMA 15.2份 | 甲苯67份 |
A5 | PEG-Br 7.7份 | DMAEMA 13.1份 | MMA 12.5份 | 甲苯67份 |
A6 | PEG-Br 9份 | DHPMA 9份 | MMA 15.3份 | 甲苯67份 |
A7 | PEG-Br 6.9份 | DHPMA 13.7份 | MMA 12.7份 | 甲苯67份 |
A8 | PEG-Br 16.6份 | MMA 11.1份 | DMAEMA 5.6份 | 甲苯67份 |
A9 | PEG-Br 9.1份 | MMA 13.5份 | DMAEMA 10.7份 | 甲苯67份 |
A10 | PEG-Br 16.5份 | MMA 11份 | DHPMA 5.6份 | 甲苯67份 |
A11 | PEG-Br 14份 | MMA 9.3份 | DHPMA 9.8份 | 甲苯67份 |
A12 | E2BiB 0.8份 | MMA 8.8份 | DMAEMA 23.8份 | 甲苯67份 |
A13 | E2BiB 0.9份 | MMA 13.6份 | DHPMA 18.9份 | 甲苯67份 |
A14 | E2BiB 08份 | MMA 10.3份 | DMAEMA 16.2份DHPMA 6份 | 甲苯67份 |
A15 | E2BiB 0.9份 | MMA 14.2份 | DMAEMA 13.3份DHPMA 4.9份 | 甲苯67份 |
A16 | E2BiB 0.7份 | MMA 10.6份 | NHSMA 19.4份 | DMSO 70份 |
A17 | E2BiB 0.6份 | MMA 115份 | NHSMA 31.6份 | DMSO 70份 |
A18 | E2BiB 0.7份 | MMA 7.3份 | NHSMA 20.1份 | DMSO 70份 |
A19 | BPDB 0.8份 | PEGMA2 21份MMA 7份 | NHSMA 3份 | 甲苯69份 |
A20 | BPDB 0.8份 | PEGMA2 20份MMA 6份 | NHSMA 4.5份 | 甲苯69份 |
A21 | BPDB 08份 | PEGMA1 22.3份MMA 63份 | NHSMA 19份 | 甲苯69份 |
A22 | BPDB 0.8份 | PEGMA1 21份MMA 5.9份 | NHSMA 3.6份 | 甲苯69份 |
实施例A23-30
这些聚合分散剂是这样制得,首先使用催化链转移聚合反应以预备大分子单体“臂”片段,其再与单体共聚合以形成“主链”片段。链转移催化剂是二(甲醇)-二(二甲基glyoximate-二氟化硼)钴(II)[CoBF],为Haddleton等人在Journal of Polymer Science Part A-Polymer Chemistry 2001,39(14),2378中所述。使用聚合反应引发剂偶氮二(2,4-二甲基戊腈[V-65]、偶氮二(2-异丙基-4,5-二氢-1H-咪唑二盐酸化物)[VA-044]及二甲基-2,2′-偶氮二(2-甲基丙酸酯)[V601](全部来自Wako GMBH,Neuss,DE)。
实施例A23
向装有热电偶、回流冷凝器、顶部搅拌器、保持惰性大气遍及反应的过程中的氮进气口的夹套反应器中,加入部分1,喷射氮气1小时除去氧气,然后加热至回流(92℃)。向反应器中加入先前脱氧的部分2,含部分2的导管也用加入反应器的脱氧的部分3冲洗。脱氧的部分4和5是使用二流速控制泵同时加入反应器,同时反应混合物保持回流。在90分钟之内加入首先的52.9%的部分4,剩下的47.1%在240分钟内加入。对于部分5,在1 20分钟之内加入首先的67.5%,剩下的32.5%在120分钟内加入。完成加入部分4和5之后,反应混合物再保持回流45分钟,之后在室温下冷却。在真空下除去溶剂得到产物,为粘稠、黄色/橙色油。
部分1 | DMAEMA异丙醇 | 202.5份259.8份 |
部分2 | 异丙醇甲基乙基酮CoBFV-65 | 18.8份8.0份0.0082份0.2份 |
部分3 | 异丙醇 | 15.7份 |
部分4 | 异丙醇甲基乙基酮CoBFV-65 | 56.1份24.1份0.0168份2.2份 |
部分5 | DMAEMA | 182.5份 |
实施例A24
向装有热电偶、回流冷凝器、顶部搅拌器、保持惰性大气遍及反应的过程中的氮进气口的夹套反应器中,加入部分1,喷射氮气2小时除去氧气,然后加热至55℃。加入部分2,先前脱氧的部分3使用流速控制泵注入水性溶液,53分钟内速率8.5ml/min。反应在55℃下再保持2小时,之后真空下除去溶剂,以得到白色固体产物。
部分1 | 去离子水CoBF | 954份0.032份 |
部分2 | VA-044 | 1.71份 |
部分3 | MAACoBF | 450份0.021份 |
实施例A25
向装有热电偶、回流冷凝器、顶部搅拌器、保持惰性大气遍及反应的过程中的氮进气口的夹套反应器中,加入部分1,用氮气喷射1小时除去氧气,然后加热至回流(87℃)。把先前脱氧的部分2加入反应器,含部分2的导管也用加入反应器的部分3冲洗。脱氧的部分4和5使用流速控制泵同时加入反应器,同时反应混合物保持回流。在90分钟内加入首先54.8%的部分4,剩下的45.2%是在240分钟内加入。对于部分5,在120分钟内加入首先的67%,剩下的33%是在120分钟内加入。完成加入部分4和5之后,反应混合物再保持回流45分钟,之后在室温下冷却。在真空下除去溶剂,以得到白色固体的产物。
部分1 | MMAMAA异丙醇 | 312.7份176.3份627.4份 |
部分2 | 甲基乙基酮异丙醇CoBFV-65 | 19.9份49.9份0.0456份0.5份 |
部分3 | 异丙醇 | 41.3份 |
部分4 | 甲基乙基酮异丙醇CoBFV-65 | 59.5份148.8份0.0913份5.5份 |
部分5 | MMAMAA | 199.9份264.5份 |
实施例A26-A30
使用由实施例A23-A25中的催化链转移聚合反应制得的大分子单体制备的栉状聚合分散剂是如表2所示。在各个制备中,引发剂、单体和大分子单体溶解于装有氮进气口、橡胶隔片和磁力搅拌棒的密封管中的溶剂中。溶液是通过针头喷射氮气30分钟来除去氧气。溶液随后加热至70℃,搅拌72小时。在A26-A28的情况下,聚合物是通过在真空下除去溶剂分离。在A29和A30的情况下,聚合物是通过在二氯甲烷中沉淀而分离。
表2
实施例 | 引发剂 | 单体 | 大分子单体 | 溶剂 |
A26 | V-601 0.1份 | BA9.6份 | A2313.4份 | 异丙醇76.8份 |
A27 | V-601 0.1份 | BA5.6份 | A2317.4份 | 异丙醇76.8份 |
A28 | V-601 0.1份 | MA6.8份 | A2316.2份 | 异丙醇76.8份 |
A29 | V-601 0.1份 | BA2.2份 | A2518.1份 | 异丙醇58.7份水18.1份 |
A30 | V-601 0.1份 | BA12.1份 | A2411份 | 异丙醇76.8份水11份 |
实施例B1-B27
表3中的实施例说明了两亲的聚合分散剂在制备农药活性成分的水性混悬液中的应用。
分散液是这样制得,取1份聚合分散剂[根据以上实施例A1-A30之一制得]和0.1份非离子润湿剂(SYNPERONICTM A7,来自UniqemaLtd)放入48.9份的去离子水中,加入50份四氯二氰苯(2,4,5,6-四氯-1,3-苯二腈)。加入氧化锆碾磨小珠,分散液机械振动30分钟。评估各个分散液,使用Malvern Instruments′Mastersizer(TM)2000激光散射装置测量粒径,使用光学显微镜检查物理形态和寻找絮凝;在下表3中列出各个样品的大小的中值粒径。
表3
实施例 | 聚合物 | 粒径(μm) | 外观 |
B1 | 来自实施例A1 | 1.9 | 液体分散液无絮凝 |
B2 | 来自实施例A2 | 1.7 | 液体分散液无絮凝 |
B3 | 来自实施例A3 | 1.7 | 液体分散液无絮凝 |
B4 | 来自实施例A4 | 1.6 | 液体分散液无絮凝 |
B5 | 来自实施例A5 | 1.9 | 液体分散液无絮凝 |
B6 | 来自实施例A6 | 1.7 | 液体分散液无絮凝 |
B7 | 来自实施例A7 | 1.6 | 液体分散液无絮凝 |
B8 | 来自实施例A8 | 1.8 | 液体分散液无絮凝 |
B9 | 来自实施例A9 | 1.5 | 液体分散液无絮凝 |
B10 | 来自实施例A10 | 1.8 | 液体分散液无絮凝 |
B11 | 来自实施例A11 | 1.6 | 液体分散液无絮凝 |
B12 | 来自实施例A12 | 1.2 | 液体分散液无絮凝 |
B13 | 来自实施例A13 | 1.8 | 液体分散液无絮凝 |
B14 | 来自实施例A14 | 1.6 | 液体分散液无絮凝 |
B15 | 来自实施例A15 | 1.4 | 液体分散液无絮凝 |
B16 | 来自实施例A16 | 5.5 | 液体分散液无絮凝 |
B17 | 来自实施例A17 | 1.9 | 液体分散液无絮凝 |
B18 | 来自实施例A18 | 4.9 | 液体分散液无絮凝 |
B19 | 来自实施例A19 | 1.0 | 液体分散液无絮凝 |
B20 | 来自实施例A20 | 4.9 | 液体分散液无絮凝 |
B21 | 来自实施例A21 | 1.0 | 液体分散液无絮凝 |
B22 | 来自实施例A22 | 1.1 | 液体分散液无絮凝 |
B23 | 来自实施例A26 | 1.3 | 液体分散液无絮凝 |
B24 | 来自实施例A27 | 1.4 | 液体分散液无絮凝 |
B25 | 来自实施例A28 | 2.8 | 液体分散液无絮凝 |
B26 | 来自实施例A29 | 2.5 | 液体分散液无絮凝 |
B27 | 来自实施例A30 | 1.9 | 液体分散液无絮凝 |
实施例C1-C14
这些实施例证明了,交联聚合分散剂[通过位于可溶于连续溶液的聚合物片段上的反应部分]产生更稳定的分散液,当使用相同的聚合分散剂时与没有交联时相比,其中分散剂是更难于从固体颗粒表面转移。
交联化合物的溶液是加入实施例B的分散液。在C1的情况下,在pH9下把1份二-(碘代乙氧基)乙烷[BIEE](来自Sigma Aldrich)的丙酮(1份比9份)的溶液加入9份的分散液,在C2-C14的情况下,在pH7下把1份三官能的氮杂环丙烷交联剂的水(1份比9份)的溶液加入9份的分散液。使用的三官能的氮杂环丙烷类是CX-100(来自NeoResins,Waalwijk,NL)和XAMA-2(来自Flevo Chemie,HarderWijk,NL)。然后在20℃下,分散液在辊道上摇动16小时,之后其用去离子水稀释(1份分散液比9份水),加入丙酮引起稳定聚合物的脱附。表4显示了,把相同量的丙酮加入两种分散液的实验的比较,如上所述一种加入交联剂,一种没有没有加入交联剂。
表4
实施例 | 分散液 | 交联剂 | 加交联剂的 | 未加交联剂的 |
C1 | 来自B12 | BIBE | 液体分散液 | 絮凝的颗粒 |
C2 | 来自B16 | CX-100 | 液体分散液 | 絮凝的颗粒 |
C3 | 来自B17 | CX-100 | 液体分散液 | 絮凝的颗粒 |
C4 | 来自B17 | XAMA-2 | 液体分散液 | 絮凝的颗粒 |
C5 | 来自B18 | XAMA-2 | 液体分散液 | 絮凝的颗粒 |
C6 | 来自B19 | CX-100 | 液体分散液 | 絮凝的颗粒 |
C7 | 来自B19 | XAMA-2 | 液体分散液 | 絮凝的颗粒 |
C8 | 来自B20 | CX-100 | 液体分散液 | 絮凝的颗粒 |
C9 | 来自B20 | XAMA-2 | 液体分散液 | 絮凝的颗粒 |
C10 | 来自B21 | XAMA-2 | 液体分散液 | 絮凝的颗粒 |
C11 | 来自B22 | XAMA-2 | 液体分散液 | 絮凝的颗粒 |
C12 | 来自B22 | CX-100 | 液体分散液 | 絮凝的颗粒 |
C13 | 来自B26 | XAMA-2 | 液体分散液 | 絮凝的颗粒 |
C14 | 来自B27 | XAMA-2 | 液体分散液 | 絮凝的颗粒 |
Claims (6)
1.一种在液体连续相中含固体颗粒或液滴的不连续相的分散液;具有在连续相可溶的片段和在连续相中不可溶的片段的聚合分散剂;及通过交联聚合分散剂形成的围绕不连续相的固体颗粒或液滴网状结构;其中交联是在可溶于连续相的片段之间。
2.权利要求1的分散液,其中聚合分散剂具有可溶于连续相的第二片段,而且该第二可溶的片段是化学上不同于权利要求1的可溶片段。
3.权利要求1或2的分散液,其中连续相是水性基的。
4.权利要求1、2或3的分散液,其中是农药分散液。
5.权利要求4的分散液,其中不连续相是含农药的固体颗粒。
6.权利要求4的分散液,其中不连续相是含农药的液滴。
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CN107001639A (zh) * | 2015-11-25 | 2017-08-01 | 株式会社Lg化学 | 两亲性聚合物 |
CN111315217A (zh) * | 2017-10-31 | 2020-06-19 | 悉尼大学 | 新型聚合物包覆的百菌清颗粒 |
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UY31209A1 (es) * | 2007-07-06 | 2009-01-30 | Basf Se | Uso de homo y copolimeros para la estabilización de formulaciones de principios activos |
CA2781637A1 (en) * | 2009-11-27 | 2011-06-03 | Basf Se | Dendritic polyurea for solubilizing active substances of low solubility |
RU2469536C1 (ru) * | 2011-06-16 | 2012-12-20 | Государственное бюджетное учреждение Республики Башкортостан "Научно-исследовательский технологический институт гербицидов и регуляторов роста растений с опытно-экспериментальным производством Академии наук Республики Башкортостан" | Фунгицидное средство и способ его получения |
JP2016052613A (ja) * | 2014-09-02 | 2016-04-14 | 国立大学法人 千葉大学 | コアシェル粒子 |
KR102001614B1 (ko) * | 2015-11-25 | 2019-07-18 | 주식회사 엘지화학 | 양친성 고분자 |
KR102184376B1 (ko) * | 2015-11-25 | 2020-11-30 | 주식회사 엘지화학 | 양친성 고분자를 포함하는 미셀 |
KR102009969B1 (ko) * | 2015-11-25 | 2019-10-21 | 주식회사 엘지화학 | 양친성 고분자 |
TW201730284A (zh) * | 2015-12-07 | 2017-09-01 | Mitsubishi Chem Corp | 非溶解性防污塗料用聚合物、樹脂組成物、防污塗料、塗膜、水中摩擦降低方法及非溶解性防污塗料用聚合物的製造方法 |
US11160755B2 (en) * | 2016-06-16 | 2021-11-02 | Lg Chem, Ltd. | Amphiphilic polymer |
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JP7305232B1 (ja) | 2022-12-14 | 2023-07-10 | 竹本油脂株式会社 | 結晶成長抑制剤、及びそれを含有する農薬組成物 |
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US4448929A (en) * | 1981-08-26 | 1984-05-15 | Stauffer Chemical Company | Encapsulation process |
JP2001508762A (ja) * | 1996-06-27 | 2001-07-03 | ジー.ディー.サール アンド カンパニー | 架橋した外殻領域および内部芯領域を有する両親媒性コポリマーからなり、医薬およびその他の用途に有用な粒子 |
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CN107001639A (zh) * | 2015-11-25 | 2017-08-01 | 株式会社Lg化学 | 两亲性聚合物 |
TWI662970B (zh) * | 2015-11-25 | 2019-06-21 | 南韓商Lg化學股份有限公司 | 兩親媒性聚合物 |
US10328024B2 (en) | 2015-11-25 | 2019-06-25 | Lg Chem, Ltd. | Amphiphilic polymer |
US10857099B2 (en) | 2015-11-25 | 2020-12-08 | Lg Chem, Ltd. | Amphiphilic polymer |
CN111315217A (zh) * | 2017-10-31 | 2020-06-19 | 悉尼大学 | 新型聚合物包覆的百菌清颗粒 |
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