CA2381514A1 - Procede de preparation de melanges maitres de silice-caoutchouc a base de latex de poymeres - Google Patents
Procede de preparation de melanges maitres de silice-caoutchouc a base de latex de poymeres Download PDFInfo
- Publication number
- CA2381514A1 CA2381514A1 CA002381514A CA2381514A CA2381514A1 CA 2381514 A1 CA2381514 A1 CA 2381514A1 CA 002381514 A CA002381514 A CA 002381514A CA 2381514 A CA2381514 A CA 2381514A CA 2381514 A1 CA2381514 A1 CA 2381514A1
- Authority
- CA
- Canada
- Prior art keywords
- silica
- masterbatch
- process defined
- particles
- latex
- 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.)
- Abandoned
Links
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims abstract description 299
- 229920000126 latex Polymers 0.000 title claims abstract description 74
- 229920001971 elastomer Polymers 0.000 title claims abstract description 45
- 239000005060 rubber Substances 0.000 title claims abstract description 40
- 229920000642 polymer Polymers 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims description 45
- 230000008569 process Effects 0.000 title claims description 35
- 239000000377 silicon dioxide Substances 0.000 title abstract description 143
- 238000002360 preparation method Methods 0.000 title description 6
- 239000004594 Masterbatch (MB) Substances 0.000 claims abstract description 76
- 239000004816 latex Substances 0.000 claims abstract description 61
- 239000002245 particle Substances 0.000 claims abstract description 49
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 32
- 239000002002 slurry Substances 0.000 claims description 25
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 19
- 239000007822 coupling agent Substances 0.000 claims description 15
- 239000004744 fabric Substances 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000000945 filler Substances 0.000 claims description 10
- 230000001112 coagulating effect Effects 0.000 claims description 8
- 229920000459 Nitrile rubber Polymers 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- -1 poly(acrylates) Polymers 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 239000005062 Polybutadiene Substances 0.000 claims description 4
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- 229920002857 polybutadiene Polymers 0.000 claims description 4
- 244000043261 Hevea brasiliensis Species 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 229920001084 poly(chloroprene) Polymers 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims 1
- 229920003052 natural elastomer Polymers 0.000 claims 1
- 229920001194 natural rubber Polymers 0.000 claims 1
- 229920002223 polystyrene Polymers 0.000 claims 1
- 229920000915 polyvinyl chloride Polymers 0.000 claims 1
- 239000004800 polyvinyl chloride Substances 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 29
- 239000011707 mineral Substances 0.000 abstract description 29
- 239000006229 carbon black Substances 0.000 abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 3
- 239000004927 clay Substances 0.000 abstract description 3
- 229910052570 clay Inorganic materials 0.000 abstract description 3
- 150000004760 silicates Chemical class 0.000 abstract description 3
- 239000004408 titanium dioxide Substances 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000000725 suspension Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- 210000002966 serum Anatomy 0.000 description 27
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 22
- 125000003342 alkenyl group Chemical group 0.000 description 21
- 239000002253 acid Substances 0.000 description 19
- 238000001914 filtration Methods 0.000 description 18
- 238000007792 addition Methods 0.000 description 17
- LQPIXHMFCAPWFK-USGGBSEESA-N [(z)-octadec-9-enyl]-(3-trimethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC\C=C/CCCCCCCC[NH2+]CCC[Si](OC)(OC)OC LQPIXHMFCAPWFK-USGGBSEESA-N 0.000 description 16
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 15
- 239000006185 dispersion Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000005345 coagulation Methods 0.000 description 12
- 230000015271 coagulation Effects 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000010692 aromatic oil Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000012216 screening Methods 0.000 description 11
- 235000019241 carbon black Nutrition 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 230000002209 hydrophobic effect Effects 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000001117 sulphuric acid Substances 0.000 description 8
- 235000011149 sulphuric acid Nutrition 0.000 description 8
- 238000004073 vulcanization Methods 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 239000011236 particulate material Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000005864 Sulphur Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229920001897 terpolymer Polymers 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- FSMHYZUFHYGNHS-UHFFFAOYSA-N 3-[ethoxy-di(propan-2-yl)silyl]propan-1-amine Chemical compound CCO[Si](C(C)C)(C(C)C)CCCN FSMHYZUFHYGNHS-UHFFFAOYSA-N 0.000 description 2
- SWDDLRSGGCWDPH-UHFFFAOYSA-N 4-triethoxysilylbutan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCCN SWDDLRSGGCWDPH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical group 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 238000005189 flocculation Methods 0.000 description 2
- 230000016615 flocculation Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 229920006173 natural rubber latex Polymers 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- AITWEOSZOXKPNO-UHFFFAOYSA-N 1,1'-biphenyl;guanidine Chemical compound NC(N)=N.C1=CC=CC=C1C1=CC=CC=C1 AITWEOSZOXKPNO-UHFFFAOYSA-N 0.000 description 1
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- LOVYCUYJRWLTSU-UHFFFAOYSA-N 2-(3,4-dichlorophenoxy)-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC=C(Cl)C(Cl)=C1 LOVYCUYJRWLTSU-UHFFFAOYSA-N 0.000 description 1
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 description 1
- PJURIXUDYDHOMA-UHFFFAOYSA-N 3-[tris[2-(2-methoxyethoxy)ethoxy]silyl]propan-1-amine Chemical compound COCCOCCO[Si](CCCN)(OCCOCCOC)OCCOCCOC PJURIXUDYDHOMA-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- YQHDQYPKFWETPO-UHFFFAOYSA-N 4-[methoxy(dimethyl)silyl]butan-1-amine Chemical compound CO[Si](C)(C)CCCCN YQHDQYPKFWETPO-UHFFFAOYSA-N 0.000 description 1
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- LQHLAMHHCBUQTQ-UHFFFAOYSA-N CCCCC(CC)CO[Si] Chemical compound CCCCC(CC)CO[Si] LQHLAMHHCBUQTQ-UHFFFAOYSA-N 0.000 description 1
- 229920008327 Carbomix Polymers 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 239000004908 Emulsion polymer Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000006237 Intermediate SAF Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- DGYZLCMWIBUSFR-UHFFFAOYSA-N N'-(2-aminoethyl)-N,1,1-triethoxy-N-(3-silylpropyl)ethane-1,2-diamine Chemical compound C(C)OC(N(CCC[SiH3])OCC)(CNCCN)OCC DGYZLCMWIBUSFR-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001495454 Parthenium Species 0.000 description 1
- 241001495453 Parthenium argentatum Species 0.000 description 1
- 229920013648 Perbunan Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- GSFXLBMRGCVEMO-UHFFFAOYSA-N [SiH4].[S] Chemical compound [SiH4].[S] GSFXLBMRGCVEMO-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229920001893 acrylonitrile styrene Polymers 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- UHVCSNKHFBQKBO-UHFFFAOYSA-N benzyl-ethenyl-[2-(3-trimethoxysilylpropylamino)ethyl]azanium;chloride Chemical compound Cl.CO[Si](OC)(OC)CCCNCCN(C=C)CC1=CC=CC=C1 UHVCSNKHFBQKBO-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- RTACIUYXLGWTAE-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene;styrene Chemical compound C=CC=C.CC(=C)C=C.C=CC1=CC=CC=C1 RTACIUYXLGWTAE-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000006231 channel black Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- AYPNJGZLSSCEKF-UHFFFAOYSA-N cyclohexyl-[diethoxy(methyl)silyl]methanamine Chemical compound CCO[Si](C)(OCC)C(N)C1CCCCC1 AYPNJGZLSSCEKF-UHFFFAOYSA-N 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- 230000005660 hydrophilic surface Effects 0.000 description 1
- 239000004569 hydrophobicizing agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000006233 lamp black Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- AMVXVPUHCLLJRE-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)hexane-1,6-diamine Chemical compound CO[Si](OC)(OC)CCCNCCCCCCN AMVXVPUHCLLJRE-UHFFFAOYSA-N 0.000 description 1
- NHBRUUFBSBSTHM-UHFFFAOYSA-N n'-[2-(3-trimethoxysilylpropylamino)ethyl]ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCCN NHBRUUFBSBSTHM-UHFFFAOYSA-N 0.000 description 1
- CHHJMNRSGVDMLK-UHFFFAOYSA-N n'-[2-[dimethoxy(phenyl)silyl]oxyethyl]ethane-1,2-diamine Chemical compound NCCNCCO[Si](OC)(OC)C1=CC=CC=C1 CHHJMNRSGVDMLK-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- ZRKGYQLXOAHRRN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropylsulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSCCC[Si](OCC)(OCC)OCC ZRKGYQLXOAHRRN-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- KLFNHRIZTXWZHT-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltrisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSCCC[Si](OCC)(OCC)OCC KLFNHRIZTXWZHT-UHFFFAOYSA-N 0.000 description 1
- GBGATMPHTZEUHH-UHFFFAOYSA-N trimethoxysilane hydrochloride Chemical compound Cl.CO[SiH](OC)OC GBGATMPHTZEUHH-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
- C08L21/02—Latex
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Paints Or Removers (AREA)
Abstract
La présente invention concerne un mélange maître de polymère garni à base de polymères dérivés du latex, ainsi que son procédé de préparation. Dans un de ses modes de réalisation, la présente invention concerne l'hydrophobisation de particules, en particulier de particules minérales hydrophiliques possédant des groupes hydroxyles en surface, notamment, de la silice, des silicates, de l'argile, de l'alumine, du dioxyde de titane et analogues. L'invention concerne également le traitement de particules non-minérales, à savoir de noir de carbone. Dans un autre de ses modes de réalisation, la présente invention concerne également un latex de polymères garni, plus particulièrement, de la silice garnie. Dans un autre mode de réalisation encore, cette invention concerne un mélange maître de silice-caoutchouc, et son procédé de préparation.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14819699P | 1999-08-10 | 1999-08-10 | |
US60/148,196 | 1999-08-10 | ||
PCT/EP2000/007634 WO2001010946A2 (fr) | 1999-08-10 | 2000-08-07 | Procede de preparation de melanges maitres de silice-caoutchouc a base de latex de poymeres |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2381514A1 true CA2381514A1 (fr) | 2001-02-15 |
Family
ID=22524711
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002381514A Abandoned CA2381514A1 (fr) | 1999-08-10 | 2000-08-07 | Procede de preparation de melanges maitres de silice-caoutchouc a base de latex de poymeres |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1208145A2 (fr) |
JP (1) | JP2003506549A (fr) |
KR (1) | KR20020021407A (fr) |
AU (1) | AU6836000A (fr) |
BR (1) | BR0013088A (fr) |
CA (1) | CA2381514A1 (fr) |
WO (1) | WO2001010946A2 (fr) |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU785282B2 (en) | 2001-06-20 | 2006-12-21 | Rohm And Haas Company | Coating with improved hiding, compositions prepared therewith, and processes for the preparation thereof |
US8822569B2 (en) | 2001-06-20 | 2014-09-02 | Rohm And Haas Company | Composite particles |
JP4586468B2 (ja) * | 2004-09-15 | 2010-11-24 | 横浜ゴム株式会社 | シリカマスターバッチの製造方法及びそのマスターバッチを含むゴム組成物 |
BRPI0617261A2 (pt) * | 2005-09-23 | 2011-07-19 | Trican Well Service Ltd | composições lodosas e métodos para produzir as mesmas |
JP5738179B2 (ja) | 2008-04-14 | 2015-06-17 | 株式会社ブリヂストン | 天然ゴムラテックスからのゴムの回収方法 |
JP2010189511A (ja) * | 2009-02-17 | 2010-09-02 | Toyo Tire & Rubber Co Ltd | マスターバッチの製造方法 |
RU2012133281A (ru) | 2010-01-07 | 2014-02-20 | Лайен Кополимер, Ллс | Композиции, содержащие компатибилизированный диоксид кремния, нитрильный каучук, бутадиен-стирольный каучук, эластомерные соединения и/или вторично используемые материалы |
PL231315B1 (pl) * | 2010-09-15 | 2019-02-28 | Cabot Corp | Kompozyt elastomerowy i sposób wytwarzania kompozytu elastomerowego |
FR2969624B1 (fr) | 2010-12-23 | 2013-02-08 | Michelin Soc Tech | Procede de preparation d'un melange-maitre en phase liquide |
KR101240602B1 (ko) | 2010-12-24 | 2013-03-06 | 금호석유화학 주식회사 | 유기 실리카 함유 마스터 배치 탄성체 및 그 제조방법 |
FR2974093B1 (fr) * | 2011-04-15 | 2015-05-08 | Michelin Soc Tech | Procede de preparation d'un melange maitre d'elastomere et d'une charge inorganique renforcante |
JP5802439B2 (ja) * | 2011-06-02 | 2015-10-28 | 東洋ゴム工業株式会社 | シリカ含有ゴムマスターバッチの製造方法 |
KR101414234B1 (ko) * | 2012-02-08 | 2014-07-01 | 한국신발피혁연구원 | 내마모성과 데브리스가 개선된 열가소성 탄성체 조성물 및 이의 제조방법 |
ES2710791T3 (es) | 2012-03-06 | 2019-04-26 | Bridgestone Corp | Procesos para recuperar caucho de briquetas envejecidas y briquetas envejecidas que contienen materia vegetal procedente de plantas que no son Hevea |
CN104395349B (zh) | 2012-05-16 | 2017-09-22 | 株式会社普利司通 | 含有经提纯的非三叶橡胶的组合物以及相关的提纯方法 |
AU2013277335B2 (en) | 2012-06-18 | 2016-08-11 | Bridgestone Corporation | Systems and methods for the management of waste associated with processing guayule shrubs to extract rubber |
WO2013192227A1 (fr) | 2012-06-18 | 2013-12-27 | Bridgestone Corporation | Procédés de désolvantisation de la bagasse |
ES2633958T3 (es) | 2012-06-18 | 2017-09-26 | Bridgestone Corporation | Métodos para aumentar el contenido en caucho extraíble de materia vegetal distinta de hevea |
KR101397138B1 (ko) * | 2012-06-29 | 2014-05-19 | 한국신발피혁연구원 | 내마모성과 마킹방지 특성이 향상된 열가소성 탄성체 조성물 |
KR101482244B1 (ko) * | 2013-04-17 | 2015-01-14 | 한국신발피혁연구원 | 내마모성과 마킹방지 특성 및 인열강도가 향상된 열가소성 탄성체 조성물 및 이의 제조방법 |
WO2015038707A1 (fr) | 2013-09-11 | 2015-03-19 | Bridgestone Corporation | Procédés pour extraire du caoutchouc de matière végétale de tks |
PL3010856T3 (pl) * | 2014-03-07 | 2019-04-30 | Ind Negromex S A De C V | Przedmieszka krzemionkowa wykonana z gumy otrzymanej w emulsji i gumy otrzymanej w roztworze |
GB2556569B (en) | 2015-07-15 | 2021-04-14 | Cabot Corp | Methods of making an elastomer composite reinforced with silica and products containing same |
WO2017011561A1 (fr) | 2015-07-15 | 2017-01-19 | Cabot Corporation | Procédés de fabrication d'un composite élastomère renforcé de silice et produits le contenant |
KR102230854B1 (ko) | 2018-10-02 | 2021-03-24 | 금호석유화학 주식회사 | 유기 실리카 함유 마스터 배치 탄성체 조성물 |
US10775105B2 (en) | 2018-11-19 | 2020-09-15 | Bridgestone Corporation | Methods for the desolventization of bagasse |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5869550A (en) * | 1995-05-22 | 1999-02-09 | Cabot Corporation | Method to improve traction using silicon-treated carbon blacks |
CA2205789A1 (fr) * | 1997-05-22 | 1998-11-22 | Bayer Inc. | Procede pour rendre des particules hydrophobes; leur emploi comme charges dans des melanges maitres polymeriques |
CA2216062A1 (fr) * | 1997-09-19 | 1999-03-19 | Bayer Inc. | Composition de caoutchouc contenant de la silice |
-
2000
- 2000-08-07 EP EP00956405A patent/EP1208145A2/fr not_active Withdrawn
- 2000-08-07 CA CA002381514A patent/CA2381514A1/fr not_active Abandoned
- 2000-08-07 JP JP2001515748A patent/JP2003506549A/ja active Pending
- 2000-08-07 AU AU68360/00A patent/AU6836000A/en not_active Abandoned
- 2000-08-07 KR KR1020027001866A patent/KR20020021407A/ko not_active Application Discontinuation
- 2000-08-07 WO PCT/EP2000/007634 patent/WO2001010946A2/fr not_active Application Discontinuation
- 2000-08-07 BR BR0013088-5A patent/BR0013088A/pt not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
WO2001010946A3 (fr) | 2002-03-07 |
WO2001010946A2 (fr) | 2001-02-15 |
AU6836000A (en) | 2001-03-05 |
BR0013088A (pt) | 2002-04-23 |
JP2003506549A (ja) | 2003-02-18 |
EP1208145A2 (fr) | 2002-05-29 |
KR20020021407A (ko) | 2002-03-20 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FZDE | Discontinued |