NZ540079A - Stabilisation of particulate suspensions by useing reactive polymeric surfactants - Google Patents
Stabilisation of particulate suspensions by useing reactive polymeric surfactantsInfo
- Publication number
- NZ540079A NZ540079A NZ540079A NZ54007903A NZ540079A NZ 540079 A NZ540079 A NZ 540079A NZ 540079 A NZ540079 A NZ 540079A NZ 54007903 A NZ54007903 A NZ 54007903A NZ 540079 A NZ540079 A NZ 540079A
- Authority
- NZ
- New Zealand
- Prior art keywords
- cross
- linking
- diisocyanate
- methacrylate
- group
- Prior art date
Links
- 239000000725 suspension Substances 0.000 title claims abstract description 33
- 239000004094 surface-active agent Substances 0.000 title claims description 59
- 230000006641 stabilisation Effects 0.000 title description 7
- 238000004132 cross linking Methods 0.000 claims abstract description 108
- 239000000178 monomer Substances 0.000 claims abstract description 105
- 239000003381 stabilizer Substances 0.000 claims abstract description 72
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 69
- 238000000034 method Methods 0.000 claims abstract description 61
- 238000006243 chemical reaction Methods 0.000 claims abstract description 59
- 239000008346 aqueous phase Substances 0.000 claims abstract description 46
- 239000007787 solid Substances 0.000 claims abstract description 43
- 125000000524 functional group Chemical group 0.000 claims abstract description 35
- 239000003905 agrochemical Substances 0.000 claims abstract description 33
- 239000000126 substance Substances 0.000 claims abstract description 27
- 125000002348 vinylic group Chemical group 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 18
- 230000002708 enhancing effect Effects 0.000 claims abstract description 4
- -1 phenyloxy Chemical group 0.000 claims description 55
- 229920000642 polymer Polymers 0.000 claims description 41
- 239000002245 particle Substances 0.000 claims description 37
- 239000003999 initiator Substances 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 29
- 229920001577 copolymer Polymers 0.000 claims description 29
- 229920001400 block copolymer Polymers 0.000 claims description 23
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 19
- 239000012948 isocyanate Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 150000002513 isocyanates Chemical class 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims description 14
- 239000005660 Abamectin Substances 0.000 claims description 14
- 239000002202 Polyethylene glycol Substances 0.000 claims description 14
- 229950008167 abamectin Drugs 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 229920001223 polyethylene glycol Polymers 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 101100188555 Arabidopsis thaliana OCT6 gene Proteins 0.000 claims description 10
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 10
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 10
- 229920001451 polypropylene glycol Polymers 0.000 claims description 10
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000003801 milling Methods 0.000 claims description 9
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 9
- ZEWLHMQYEZXSBH-UHFFFAOYSA-N 4-[2-(2-methylprop-2-enoyloxy)ethoxy]-4-oxobutanoic acid Chemical compound CC(=C)C(=O)OCCOC(=O)CCC(O)=O ZEWLHMQYEZXSBH-UHFFFAOYSA-N 0.000 claims description 7
- 238000012546 transfer Methods 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 229920006037 cross link polymer Polymers 0.000 claims description 6
- 230000001965 increasing effect Effects 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 6
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 claims description 5
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001718 carbodiimides Chemical class 0.000 claims description 5
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical group O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 claims description 4
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 claims description 4
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 claims description 4
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 claims description 4
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 claims description 4
- QHJGZUSJKGVMTF-UHFFFAOYSA-N canolol Chemical compound COC1=CC(C=C)=CC(OC)=C1O QHJGZUSJKGVMTF-UHFFFAOYSA-N 0.000 claims description 4
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 4
- 150000002118 epoxides Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000003827 glycol group Chemical group 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 claims description 3
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- IRQWEODKXLDORP-UHFFFAOYSA-N 4-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=C)C=C1 IRQWEODKXLDORP-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- 230000002776 aggregation Effects 0.000 claims description 3
- 238000004220 aggregation Methods 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000006482 condensation reaction Methods 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- XHIRWEVPYCTARV-UHFFFAOYSA-N n-(3-aminopropyl)-2-methylprop-2-enamide;hydrochloride Chemical compound Cl.CC(=C)C(=O)NCCCN XHIRWEVPYCTARV-UHFFFAOYSA-N 0.000 claims description 3
- 230000000269 nucleophilic effect Effects 0.000 claims description 3
- 238000007344 nucleophilic reaction Methods 0.000 claims description 3
- 150000003440 styrenes Chemical class 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- CLECMSNCZUMKLM-UHFFFAOYSA-N (4-ethenylphenyl)methanol Chemical compound OCC1=CC=C(C=C)C=C1 CLECMSNCZUMKLM-UHFFFAOYSA-N 0.000 claims description 2
- TVXNKQRAZONMHJ-UHFFFAOYSA-M (4-ethenylphenyl)methyl-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=C(C=C)C=C1 TVXNKQRAZONMHJ-UHFFFAOYSA-M 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical compound C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 claims description 2
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 claims description 2
- DKBHJZFJCDOGOY-UHFFFAOYSA-N 1,4-diisocyanato-2-methylbenzene Chemical compound CC1=CC(N=C=O)=CC=C1N=C=O DKBHJZFJCDOGOY-UHFFFAOYSA-N 0.000 claims description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 claims description 2
- QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 claims description 2
- OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- HAZWONBCJXKAMF-UHFFFAOYSA-N 2-[1-[1,3-bis[2-(oxiran-2-ylmethoxy)propoxy]propan-2-yloxy]propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC(OCC(C)OCC1OC1)COCC(C)OCC1CO1 HAZWONBCJXKAMF-UHFFFAOYSA-N 0.000 claims description 2
- YOMSJEATGXXYPX-UHFFFAOYSA-N 2-methoxy-4-vinylphenol Chemical compound COC1=CC(C=C)=CC=C1O YOMSJEATGXXYPX-UHFFFAOYSA-N 0.000 claims description 2
- CWNNYYIZGGDCHS-UHFFFAOYSA-N 2-methylideneglutaric acid Chemical compound OC(=O)CCC(=C)C(O)=O CWNNYYIZGGDCHS-UHFFFAOYSA-N 0.000 claims description 2
- FYLFNXHOCPSBQL-UHFFFAOYSA-N 2-methylprop-2-enoic acid;2-(2-methylprop-2-enoyloxy)ethylphosphonic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(=O)OCCP(O)(O)=O FYLFNXHOCPSBQL-UHFFFAOYSA-N 0.000 claims description 2
- VAYMIYBJLRRIFR-UHFFFAOYSA-N 2-tolyl isocyanate Chemical compound CC1=CC=CC=C1N=C=O VAYMIYBJLRRIFR-UHFFFAOYSA-N 0.000 claims description 2
- QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 claims description 2
- NCNNNERURUGJAB-UHFFFAOYSA-N 3-[2,2-bis(3-prop-2-enoyloxypropoxymethyl)butoxy]propyl prop-2-enoate Chemical compound C=CC(=O)OCCCOCC(CC)(COCCCOC(=O)C=C)COCCCOC(=O)C=C NCNNNERURUGJAB-UHFFFAOYSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 2
- IHSFHIUGYHMYNR-UHFFFAOYSA-N 4-(3-oxobutanoyloxy)butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCCOC(=O)CC(C)=O IHSFHIUGYHMYNR-UHFFFAOYSA-N 0.000 claims description 2
- LBSXSAXOLABXMF-UHFFFAOYSA-N 4-Vinylaniline Chemical compound NC1=CC=C(C=C)C=C1 LBSXSAXOLABXMF-UHFFFAOYSA-N 0.000 claims description 2
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 claims description 2
- PHQYPLKSOUDDCV-UHFFFAOYSA-N 4-phenyl-n-propan-2-ylbut-3-en-1-amine Chemical compound CC(C)NCCC=CC1=CC=CC=C1 PHQYPLKSOUDDCV-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- XZTNLXPYTOHUBH-UHFFFAOYSA-N [2-ethenyl-3-(hydroxymethyl)-5-methoxyphenyl]methanol Chemical compound COC1=CC(CO)=C(C=C)C(CO)=C1 XZTNLXPYTOHUBH-UHFFFAOYSA-N 0.000 claims description 2
- LOPVAWVHGAWUPS-UHFFFAOYSA-M [2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl]-trimethylazanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC(O)C[N+](C)(C)C LOPVAWVHGAWUPS-UHFFFAOYSA-M 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
- 229940124277 aminobutyric acid Drugs 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical class CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
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- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
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- SZBXTBGNJLZMHB-UHFFFAOYSA-N 1-chloro-2,4-diisocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1N=C=O SZBXTBGNJLZMHB-UHFFFAOYSA-N 0.000 claims 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims 1
- KUQRLZZWFINMDP-BGNLRFAXSA-N 2-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KUQRLZZWFINMDP-BGNLRFAXSA-N 0.000 claims 1
- XSHISXQEKIKSGC-UHFFFAOYSA-N 2-aminoethyl 2-methylprop-2-enoate;hydron;chloride Chemical compound Cl.CC(=C)C(=O)OCCN XSHISXQEKIKSGC-UHFFFAOYSA-N 0.000 claims 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 claims 1
- AJDUFBRFVYQOLP-UHFFFAOYSA-N 2-methylidenebutanedioic acid 2-[2-(2-methylprop-2-enoyloxy)ethoxycarbonyl]benzoic acid Chemical compound OC(=O)CC(=C)C(O)=O.CC(=C)C(=O)OCCOC(=O)C1=CC=CC=C1C(O)=O AJDUFBRFVYQOLP-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- 229920000562 Poly(ethylene adipate) Polymers 0.000 claims 1
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- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Graft Or Block Polymers (AREA)
- Polarising Elements (AREA)
- Polymerisation Methods In General (AREA)
- Steroid Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Colloid Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0228537.7A GB0228537D0 (en) | 2002-12-06 | 2002-12-06 | Particulate suspensions |
| PCT/GB2003/005291 WO2004052099A2 (en) | 2002-12-06 | 2003-12-05 | Particulate suspensions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ540079A true NZ540079A (en) | 2006-12-22 |
Family
ID=9949232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ540079A NZ540079A (en) | 2002-12-06 | 2003-12-05 | Stabilisation of particulate suspensions by useing reactive polymeric surfactants |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US20060116290A1 (enExample) |
| EP (1) | EP1569512B1 (enExample) |
| JP (2) | JP4791042B2 (enExample) |
| CN (1) | CN1744815B (enExample) |
| AT (1) | ATE354955T1 (enExample) |
| AU (1) | AU2003292383C1 (enExample) |
| BR (1) | BR0316838B1 (enExample) |
| CA (1) | CA2508553C (enExample) |
| DE (1) | DE60312209T2 (enExample) |
| DK (1) | DK1569512T3 (enExample) |
| EA (1) | EA008597B1 (enExample) |
| ES (1) | ES2279176T3 (enExample) |
| GB (1) | GB0228537D0 (enExample) |
| IL (1) | IL168970A (enExample) |
| MX (1) | MXPA05005865A (enExample) |
| NO (1) | NO332178B1 (enExample) |
| NZ (1) | NZ540079A (enExample) |
| PT (1) | PT1569512E (enExample) |
| RS (1) | RS50910B (enExample) |
| WO (1) | WO2004052099A2 (enExample) |
| ZA (1) | ZA200504014B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0505569D0 (en) * | 2005-03-18 | 2005-04-27 | Syngenta Ltd | Formulations |
| AU2007227608B2 (en) * | 2006-03-15 | 2012-08-16 | Indorama Ventures Oxides Llc | Comb polymer derivatives of polyetheramines useful as agricultural dispersants |
| US9522970B2 (en) * | 2006-10-05 | 2016-12-20 | Basf Se | Comb polymers and use thereof for the production of active or effective ingredient formulations |
| CA2691966A1 (en) * | 2007-07-06 | 2009-01-15 | Basf Se | Use of homo- and copolymers for stabilizing active ingredient formulations |
| DE102007060175A1 (de) * | 2007-12-13 | 2009-06-18 | Johannes Gutenberg-Universität Mainz | Quartärnisierung des Zusatzstoffs Aminoalkyl Methacrylat Copolymer E zur Verbesserung der Permeabilität und Löslichkeit von Arzneistoffen |
| GB0818747D0 (en) * | 2008-10-13 | 2008-11-19 | Univ Nottingham | Biocompatible responsive materials |
| US8618022B2 (en) * | 2009-07-14 | 2013-12-31 | Basf Se | Process for preparing an aqueous suspension of an organic pesticide compound |
| PT2596072E (pt) * | 2010-07-20 | 2014-09-02 | C Ip S A | Suspensão de um composto de boro |
| US20140050687A1 (en) | 2011-04-28 | 2014-02-20 | Estman Chemical Company | Betaine esters and process for making and using |
| US20120277324A1 (en) * | 2011-04-28 | 2012-11-01 | Eastman Chemical Company | Betaine esters and process for making and using |
| US10465147B2 (en) * | 2011-10-17 | 2019-11-05 | Agency For Science, Technology And Research | Copolymers |
| KR101745942B1 (ko) * | 2012-12-12 | 2017-06-27 | 한국전자통신연구원 | 카본 블랙의 표면 개질 방법 및 카본 블랙을 포함하는 표시 장치 |
| JP6535192B2 (ja) * | 2015-03-25 | 2019-06-26 | 株式会社日本触媒 | 抗菌剤 |
| CR20200230A (es) * | 2017-10-31 | 2020-09-16 | Univ Sydney | Nuevas particulas de clorotalonil recubiertas con polimero |
| GB201805083D0 (en) * | 2018-03-28 | 2018-05-09 | Croda Int Plc | Agrochemical polymer dispersants |
| KR102813594B1 (ko) * | 2018-05-31 | 2025-05-27 | 시카 테크놀러지 아게 | 뚜렷이 구별되는 빗살형 중합체를 제조하는 방법 |
| CN109619103B (zh) * | 2018-10-31 | 2021-03-16 | 塔里木大学 | 一种离子型高分子棉花打顶剂及其制备方法 |
| JP6914571B1 (ja) * | 2021-03-04 | 2021-08-04 | 竹本油脂株式会社 | 粒状農薬組成物用分散剤及びそれを含む粒状農薬組成物 |
| CN115155337B (zh) * | 2022-06-29 | 2023-10-27 | 福州大学 | 一种三维多孔交联阴离子交换膜的制备方法 |
| CN116515036B (zh) * | 2023-04-28 | 2023-10-24 | 济源市鲁泰纳米材料有限公司 | 一种用于包覆纳米氧化锌的聚合物材料及其制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0007731A3 (en) * | 1978-07-28 | 1980-02-20 | Imperial Chemical Industries Plc | Process for the production of dispersions of hydrophobic particulate solids (e.g. pesticides) and the particulate dispersions thus obtained |
| US6262152B1 (en) * | 1998-10-06 | 2001-07-17 | E. I. Du Pont De Nemours And Company | Particles dispersed w/polymer dispersant having liquid soluble and cross-linkable insoluble segments |
| GB0114197D0 (en) * | 2001-06-11 | 2001-08-01 | Syngenta Ltd | Reactive polymeric surfactants |
-
2002
- 2002-12-06 GB GBGB0228537.7A patent/GB0228537D0/en not_active Ceased
-
2003
- 2003-12-05 EA EA200500925A patent/EA008597B1/ru not_active IP Right Cessation
- 2003-12-05 RS YUP-2005/0434A patent/RS50910B/sr unknown
- 2003-12-05 DK DK03767960T patent/DK1569512T3/da active
- 2003-12-05 CA CA2508553A patent/CA2508553C/en not_active Expired - Fee Related
- 2003-12-05 BR BRPI0316838-7A patent/BR0316838B1/pt not_active IP Right Cessation
- 2003-12-05 DE DE60312209T patent/DE60312209T2/de not_active Expired - Lifetime
- 2003-12-05 CN CN200380109342.7A patent/CN1744815B/zh not_active Expired - Fee Related
- 2003-12-05 NZ NZ540079A patent/NZ540079A/en not_active IP Right Cessation
- 2003-12-05 JP JP2004558778A patent/JP4791042B2/ja not_active Expired - Fee Related
- 2003-12-05 US US10/537,467 patent/US20060116290A1/en not_active Abandoned
- 2003-12-05 AU AU2003292383A patent/AU2003292383C1/en not_active Ceased
- 2003-12-05 ES ES03767960T patent/ES2279176T3/es not_active Expired - Lifetime
- 2003-12-05 AT AT03767960T patent/ATE354955T1/de active
- 2003-12-05 PT PT03767960T patent/PT1569512E/pt unknown
- 2003-12-05 MX MXPA05005865A patent/MXPA05005865A/es active IP Right Grant
- 2003-12-05 EP EP03767960A patent/EP1569512B1/en not_active Expired - Lifetime
- 2003-12-05 WO PCT/GB2003/005291 patent/WO2004052099A2/en not_active Ceased
-
2005
- 2005-05-18 ZA ZA200504014A patent/ZA200504014B/en unknown
- 2005-06-02 IL IL168970A patent/IL168970A/en unknown
- 2005-06-06 NO NO20052711A patent/NO332178B1/no not_active IP Right Cessation
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2011
- 2011-05-18 JP JP2011111825A patent/JP2011207894A/ja active Pending
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