CA2306422C - A method of dispersing an insoluble material in an aqueous solution and an agricultural formulation - Google Patents
A method of dispersing an insoluble material in an aqueous solution and an agricultural formulation Download PDFInfo
- Publication number
- CA2306422C CA2306422C CA002306422A CA2306422A CA2306422C CA 2306422 C CA2306422 C CA 2306422C CA 002306422 A CA002306422 A CA 002306422A CA 2306422 A CA2306422 A CA 2306422A CA 2306422 C CA2306422 C CA 2306422C
- Authority
- CA
- Canada
- Prior art keywords
- comonomer
- group
- vinyl
- substituted
- alkyl
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 184
- 238000009472 formulation Methods 0.000 title claims abstract description 172
- 238000000034 method Methods 0.000 title claims abstract description 85
- 239000002198 insoluble material Substances 0.000 title claims abstract description 40
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 10
- 229920001577 copolymer Polymers 0.000 claims abstract description 129
- 239000002270 dispersing agent Substances 0.000 claims abstract description 121
- 125000001424 substituent group Chemical group 0.000 claims abstract description 95
- -1 vinyl pyrans Chemical class 0.000 claims abstract description 75
- 150000002148 esters Chemical class 0.000 claims abstract description 68
- 150000001408 amides Chemical class 0.000 claims abstract description 67
- 238000006243 chemical reaction Methods 0.000 claims abstract description 50
- 150000001336 alkenes Chemical group 0.000 claims abstract description 42
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 42
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 30
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 27
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
- 235000021317 phosphate Nutrition 0.000 claims abstract description 25
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims abstract description 25
- 150000007970 thio esters Chemical class 0.000 claims abstract description 25
- 150000002823 nitrates Chemical class 0.000 claims abstract description 24
- 239000012434 nucleophilic reagent Substances 0.000 claims abstract description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 22
- 125000000524 functional group Chemical group 0.000 claims abstract description 21
- 239000012736 aqueous medium Substances 0.000 claims abstract description 17
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 17
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Natural products CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims abstract description 11
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical class C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 claims abstract description 9
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical class C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 claims abstract description 9
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 9
- QQBUHYQVKJQAOB-UHFFFAOYSA-N 2-ethenylfuran Chemical class C=CC1=CC=CO1 QQBUHYQVKJQAOB-UHFFFAOYSA-N 0.000 claims abstract description 8
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims abstract description 8
- ORNUPNRNNSVZTC-UHFFFAOYSA-N 2-vinylthiophene Chemical class C=CC1=CC=CS1 ORNUPNRNNSVZTC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 235000001510 limonene Nutrition 0.000 claims abstract description 8
- 229940087305 limonene Drugs 0.000 claims abstract description 8
- 150000003505 terpenes Chemical class 0.000 claims abstract description 8
- 235000007586 terpenes Nutrition 0.000 claims abstract description 8
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical class C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000003871 sulfonates Chemical class 0.000 claims abstract 18
- 150000002118 epoxides Chemical class 0.000 claims abstract 13
- 125000000396 limonene group Chemical group 0.000 claims abstract 5
- 239000004562 water dispersible granule Substances 0.000 claims description 55
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000007787 solid Substances 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 239000003905 agrochemical Substances 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 239000006185 dispersion Substances 0.000 claims description 31
- 239000004563 wettable powder Substances 0.000 claims description 31
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 24
- 239000004546 suspension concentrate Substances 0.000 claims description 23
- 239000008187 granular material Substances 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 20
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 20
- 239000002245 particle Substances 0.000 claims description 19
- 239000004094 surface-active agent Substances 0.000 claims description 19
- NFJPEKRRHIYYES-UHFFFAOYSA-N methylidenecyclopentane Chemical compound C=C1CCCC1 NFJPEKRRHIYYES-UHFFFAOYSA-N 0.000 claims description 18
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 18
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 16
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 239000000080 wetting agent Substances 0.000 claims description 12
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 10
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 10
- 150000003949 imides Chemical class 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 10
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- YULMNMJFAZWLLN-UHFFFAOYSA-N methylenecyclohexane Chemical compound C=C1CCCCC1 YULMNMJFAZWLLN-UHFFFAOYSA-N 0.000 claims description 9
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 239000002736 nonionic surfactant Substances 0.000 claims description 9
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 claims description 8
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000004009 herbicide Substances 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 230000008859 change Effects 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000004185 ester group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 claims description 6
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 6
- 230000000895 acaricidal effect Effects 0.000 claims description 6
- 239000000642 acaricide Substances 0.000 claims description 6
- 239000003139 biocide Substances 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 239000000417 fungicide Substances 0.000 claims description 6
- 238000003801 milling Methods 0.000 claims description 6
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 5
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 229940124323 amoebicide Drugs 0.000 claims description 5
- 230000000507 anthelmentic effect Effects 0.000 claims description 5
- 239000000921 anthelmintic agent Substances 0.000 claims description 5
- 229940124339 anthelmintic agent Drugs 0.000 claims description 5
- 150000001555 benzenes Chemical class 0.000 claims description 5
- 150000001935 cyclohexenes Chemical class 0.000 claims description 5
- 239000001530 fumaric acid Substances 0.000 claims description 5
- 150000002240 furans Chemical class 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- 125000005395 methacrylic acid group Chemical class 0.000 claims description 5
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003750 molluscacide Substances 0.000 claims description 5
- 230000002013 molluscicidal effect Effects 0.000 claims description 5
- 230000001069 nematicidal effect Effects 0.000 claims description 5
- 239000005645 nematicide Substances 0.000 claims description 5
- 239000005648 plant growth regulator Substances 0.000 claims description 5
- 239000002423 protozoacide Substances 0.000 claims description 5
- 239000003128 rodenticide Substances 0.000 claims description 5
- 238000005507 spraying Methods 0.000 claims description 5
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 claims description 5
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 4
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- 239000003337 fertilizer Substances 0.000 claims description 3
- 239000002609 medium Substances 0.000 claims description 3
- 150000003672 ureas Chemical class 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 230000003019 stabilising effect Effects 0.000 claims description 2
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-β-pinene Chemical group C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 claims 6
- 150000001721 carbon Chemical group 0.000 claims 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 4
- 239000002917 insecticide Substances 0.000 claims 4
- 125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 claims 4
- 239000004952 Polyamide Substances 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- 229920002647 polyamide Polymers 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 239000011591 potassium Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 30
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 24
- 159000000000 sodium salts Chemical class 0.000 description 22
- 239000000178 monomer Substances 0.000 description 17
- 150000002924 oxiranes Chemical class 0.000 description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 238000003860 storage Methods 0.000 description 11
- 125000002723 alicyclic group Chemical group 0.000 description 10
- 239000000463 material Substances 0.000 description 8
- 150000003440 styrenes Chemical group 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical class NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 238000005054 agglomeration Methods 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 5
- 229920001732 Lignosulfonate Polymers 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 4
- 229920005603 alternating copolymer Polymers 0.000 description 4
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 4
- 238000001212 derivatisation Methods 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 239000004117 Lignosulphonate Substances 0.000 description 3
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- WOLATMHLPFJRGC-UHFFFAOYSA-N furan-2,5-dione;styrene Chemical compound O=C1OC(=O)C=C1.C=CC1=CC=CC=C1 WOLATMHLPFJRGC-UHFFFAOYSA-N 0.000 description 3
- 238000005469 granulation Methods 0.000 description 3
- 230000003179 granulation Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 235000019357 lignosulphonate Nutrition 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical class C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000011149 active material 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
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 238000005056 compaction Methods 0.000 description 2
- GUOAPVPPPVLIQQ-UHFFFAOYSA-N dimethyldicyclopentadiene Chemical compound C1=CC2CC1C1C2C(C)C(C)=C1 GUOAPVPPPVLIQQ-UHFFFAOYSA-N 0.000 description 2
- 229940117927 ethylene oxide Drugs 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical group CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 1
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 1
- OXLXSOPFNVKUMU-UHFFFAOYSA-N 1,4-dioctoxy-1,4-dioxobutane-2-sulfonic acid Chemical class CCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCC OXLXSOPFNVKUMU-UHFFFAOYSA-N 0.000 description 1
- TVFWYUWNQVRQRG-UHFFFAOYSA-N 2,3,4-tris(2-phenylethenyl)phenol Chemical compound C=1C=CC=CC=1C=CC1=C(C=CC=2C=CC=CC=2)C(O)=CC=C1C=CC1=CC=CC=C1 TVFWYUWNQVRQRG-UHFFFAOYSA-N 0.000 description 1
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
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- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000073 carbamate insecticide Substances 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
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- 239000003610 charcoal Substances 0.000 description 1
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 description 1
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- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical class NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
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- 230000006866 deterioration Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 description 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
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- CBYZIWCZNMOEAV-UHFFFAOYSA-N formaldehyde;naphthalene Chemical class O=C.C1=CC=CC2=CC=CC=C21 CBYZIWCZNMOEAV-UHFFFAOYSA-N 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical class O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
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- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Chemical class C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
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- 239000004407 iron oxides and hydroxides Substances 0.000 description 1
- 235000010213 iron oxides and hydroxides Nutrition 0.000 description 1
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 150000002848 norbornenes Chemical class 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
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- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 229920005613 synthetic organic polymer Polymers 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
-
- 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
- A01N25/12—Powders or granules
- A01N25/14—Powders or granules wettable
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
- A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Fertilizers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPO9767A AUPO976797A0 (en) | 1997-10-14 | 1997-10-14 | Method and composition (III) |
| AUPO9767 | 1997-10-14 | ||
| PCT/AU1998/000855 WO1999018788A1 (en) | 1997-10-14 | 1998-10-14 | A method of dispersing an insoluble material in an aqueous solution and an agricultural formulation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2306422A1 CA2306422A1 (en) | 1999-04-22 |
| CA2306422C true CA2306422C (en) | 2008-04-22 |
Family
ID=3804047
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002306422A Expired - Lifetime CA2306422C (en) | 1997-10-14 | 1998-10-14 | A method of dispersing an insoluble material in an aqueous solution and an agricultural formulation |
| CA002306421A Expired - Lifetime CA2306421C (en) | 1997-10-14 | 1998-10-14 | Method of dispersing an insoluble material in aqueous solution and agricultural formulation |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002306421A Expired - Lifetime CA2306421C (en) | 1997-10-14 | 1998-10-14 | Method of dispersing an insoluble material in aqueous solution and agricultural formulation |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US6844293B1 (enExample) |
| EP (2) | EP1024692B1 (enExample) |
| JP (4) | JP4878675B2 (enExample) |
| AU (1) | AUPO976797A0 (enExample) |
| CA (2) | CA2306422C (enExample) |
| DE (2) | DE69840411D1 (enExample) |
| ES (2) | ES2320185T3 (enExample) |
| NZ (2) | NZ503744A (enExample) |
| WO (2) | WO1999018787A1 (enExample) |
| ZA (2) | ZA989400B (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPO976797A0 (en) * | 1997-10-14 | 1997-11-06 | Orica Australia Pty Ltd | Method and composition (III) |
| GB9907668D0 (en) * | 1999-04-01 | 1999-05-26 | Zeneca Ltd | Solid composition |
| GB0012775D0 (en) * | 2000-05-26 | 2000-07-19 | Ici Plc | Agrochemical suspension formulations |
| EP1286588B1 (en) | 2000-05-26 | 2005-12-28 | Imperial Chemical Industries PLC | Agrochemical suspension formulations |
| JP4617569B2 (ja) * | 2000-12-13 | 2011-01-26 | 日本ゼオン株式会社 | 分散剤及びその使用方法 |
| EP1372385A1 (en) | 2001-03-30 | 2004-01-02 | Rhodia Inc. | Aqeuous suspension of nanoparticles comprising an agrochemical active ingredient |
| WO2007109051A2 (en) * | 2006-03-15 | 2007-09-27 | Huntsman Petrochemical Corporation | Comb polymer derivatives of polyetheramines useful as agricultural dispersants |
| BRPI0715292A2 (pt) | 2006-09-22 | 2013-06-11 | Huntsman Spec Chem Corp | inibiÇço da maturaÇço de ostwald em formulaÇÕes quÍmicas |
| CL2008001991A1 (es) * | 2007-07-06 | 2009-09-25 | Basf Se | Uso de homo y copolimeros que comprenden al menos 10% en peso de un monomero seleccionado entre acido acrilico y metacrilico y hasta 90% de uno o mas monomeros no ionicos, donde la suma de ambos es de al menos el 70% de los monomeros; composicion y preparacion del principio activo; dispersion acuosa y su preparacion. |
| US20090013599A1 (en) * | 2007-07-10 | 2009-01-15 | Peter Cordani | Water retention mixture and method for spray application |
| US7877929B2 (en) | 2007-08-04 | 2011-02-01 | Rezzorb, Llc | Method and apparatus for reducing fertilizer use in agricultural operations |
| US7785387B2 (en) * | 2007-11-01 | 2010-08-31 | Honeywell International Inc. | Chemically and physically modified fertilizers, methods of production and uses thereof |
| US20090217723A1 (en) * | 2008-03-03 | 2009-09-03 | Specialty Fertilizer Products | Dual salt fertilizer giving enhanced crop yields |
| BR112012007786B1 (pt) * | 2009-10-05 | 2021-05-18 | Specialty Fertilizer Products, Llc | composição fertilizante, método para sua preparação, e método para fertilização da terra |
| EP2600722B1 (en) * | 2010-08-06 | 2014-06-11 | Basf Se | Use of a n-vinyllactam / vinylimidazol copolymer as dispersing agent |
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-
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- 1997-10-14 AU AUPO9767A patent/AUPO976797A0/en not_active Abandoned
-
1998
- 1998-10-14 WO PCT/AU1998/000854 patent/WO1999018787A1/en not_active Ceased
- 1998-10-14 DE DE69840411T patent/DE69840411D1/de not_active Expired - Lifetime
- 1998-10-14 WO PCT/AU1998/000855 patent/WO1999018788A1/en not_active Ceased
- 1998-10-14 NZ NZ503744A patent/NZ503744A/en not_active IP Right Cessation
- 1998-10-14 JP JP2000515432A patent/JP4878675B2/ja not_active Expired - Lifetime
- 1998-10-14 EP EP98948625A patent/EP1024692B1/en not_active Revoked
- 1998-10-14 ES ES98948625T patent/ES2320185T3/es not_active Expired - Lifetime
- 1998-10-14 EP EP98948624A patent/EP1022943B1/en not_active Expired - Lifetime
- 1998-10-14 JP JP2000515431A patent/JP2001519359A/ja not_active Withdrawn
- 1998-10-14 DE DE69840410T patent/DE69840410D1/de not_active Expired - Lifetime
- 1998-10-14 ES ES98948624T patent/ES2320184T3/es not_active Expired - Lifetime
- 1998-10-14 ZA ZA989400A patent/ZA989400B/xx unknown
- 1998-10-14 CA CA002306422A patent/CA2306422C/en not_active Expired - Lifetime
- 1998-10-14 ZA ZA989399A patent/ZA989399B/xx unknown
- 1998-10-14 CA CA002306421A patent/CA2306421C/en not_active Expired - Lifetime
- 1998-10-14 NZ NZ503745A patent/NZ503745A/xx not_active IP Right Cessation
- 1998-10-14 US US09/529,495 patent/US6844293B1/en not_active Expired - Lifetime
- 1998-10-14 US US09/529,480 patent/US6855763B1/en not_active Expired - Lifetime
-
2004
- 2004-11-12 US US10/987,094 patent/US7109267B2/en not_active Expired - Lifetime
- 2004-12-09 US US11/008,309 patent/US7179859B2/en not_active Expired - Lifetime
-
2011
- 2011-04-06 JP JP2011084197A patent/JP5463319B2/ja not_active Expired - Lifetime
- 2011-04-25 JP JP2011096837A patent/JP5280481B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2306421C (en) | 2008-12-23 |
| ES2320184T3 (es) | 2009-05-19 |
| EP1022943B1 (en) | 2008-12-31 |
| DE69840411D1 (de) | 2009-02-12 |
| ZA989399B (en) | 1999-04-15 |
| EP1022943A4 (en) | 2000-12-20 |
| NZ503745A (en) | 2002-08-28 |
| DE69840410D1 (de) | 2009-02-12 |
| EP1024692B1 (en) | 2008-12-31 |
| NZ503744A (en) | 2002-05-31 |
| ZA989400B (en) | 1999-04-15 |
| US6855763B1 (en) | 2005-02-15 |
| US7179859B2 (en) | 2007-02-20 |
| EP1024692A4 (en) | 2001-01-03 |
| JP5280481B2 (ja) | 2013-09-04 |
| US7109267B2 (en) | 2006-09-19 |
| JP2001519359A (ja) | 2001-10-23 |
| EP1022943A1 (en) | 2000-08-02 |
| US6844293B1 (en) | 2005-01-18 |
| WO1999018787A1 (en) | 1999-04-22 |
| JP5463319B2 (ja) | 2014-04-09 |
| ES2320185T3 (es) | 2009-05-19 |
| JP4878675B2 (ja) | 2012-02-15 |
| JP2001519360A (ja) | 2001-10-23 |
| JP2011137041A (ja) | 2011-07-14 |
| CA2306422A1 (en) | 1999-04-22 |
| JP2011144206A (ja) | 2011-07-28 |
| CA2306421A1 (en) | 1999-04-22 |
| US20050090603A1 (en) | 2005-04-28 |
| US20050101724A1 (en) | 2005-05-12 |
| EP1024692A1 (en) | 2000-08-09 |
| AUPO976797A0 (en) | 1997-11-06 |
| WO1999018788A1 (en) | 1999-04-22 |
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