CA2289458A1 - Colloidally stabilized butadiene emulsions - Google Patents
Colloidally stabilized butadiene emulsions Download PDFInfo
- Publication number
- CA2289458A1 CA2289458A1 CA002289458A CA2289458A CA2289458A1 CA 2289458 A1 CA2289458 A1 CA 2289458A1 CA 002289458 A CA002289458 A CA 002289458A CA 2289458 A CA2289458 A CA 2289458A CA 2289458 A1 CA2289458 A1 CA 2289458A1
- Authority
- CA
- Canada
- Prior art keywords
- monomer
- emulsion polymer
- stabilized emulsion
- polymer according
- group
- 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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims description 36
- 239000000839 emulsion Substances 0.000 title description 8
- 239000000178 monomer Substances 0.000 claims abstract description 113
- 239000004908 Emulsion polymer Substances 0.000 claims abstract description 51
- 239000004094 surface-active agent Substances 0.000 claims abstract description 50
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000000084 colloidal system Substances 0.000 claims abstract description 20
- 230000001681 protective effect Effects 0.000 claims abstract description 19
- 150000002148 esters Chemical class 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 125000005702 oxyalkylene group Chemical group 0.000 claims abstract description 17
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 150000001991 dicarboxylic acids Chemical class 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000005690 diesters Chemical class 0.000 claims abstract description 6
- 150000002763 monocarboxylic acids Chemical class 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 6
- -1 poly(vinylalcohol) Polymers 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 25
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 22
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 17
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 10
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 7
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 6
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 6
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 241000416162 Astragalus gummifer Species 0.000 claims description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 3
- 239000004375 Dextrin Substances 0.000 claims description 3
- 229920001353 Dextrin Polymers 0.000 claims description 3
- 229920000084 Gum arabic Polymers 0.000 claims description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 3
- 229920000881 Modified starch Polymers 0.000 claims description 3
- 241000978776 Senegalia senegal Species 0.000 claims description 3
- 229920002125 Sokalan® Polymers 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 3
- 229920001615 Tragacanth Polymers 0.000 claims description 3
- 235000010489 acacia gum Nutrition 0.000 claims description 3
- 239000000205 acacia gum Substances 0.000 claims description 3
- 235000019425 dextrin Nutrition 0.000 claims description 3
- 239000001341 hydroxy propyl starch Substances 0.000 claims description 3
- 229920003063 hydroxymethyl cellulose Polymers 0.000 claims description 3
- 229940031574 hydroxymethyl cellulose Drugs 0.000 claims description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 3
- 235000013828 hydroxypropyl starch Nutrition 0.000 claims description 3
- 235000019426 modified starch Nutrition 0.000 claims description 3
- 239000004584 polyacrylic acid Substances 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000001993 dienes Chemical class 0.000 abstract description 3
- 238000000034 method Methods 0.000 description 12
- 238000007720 emulsion polymerization reaction Methods 0.000 description 10
- 229920000126 latex Polymers 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000004816 latex Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000013459 approach Methods 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 235000011180 diphosphates Nutrition 0.000 description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 150000004712 monophosphates Chemical class 0.000 description 2
- 229920000847 nonoxynol Polymers 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 1
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 1
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical class O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- GGZUSLXFZZJXNP-UHFFFAOYSA-N 2-(phenoxymethyl)oxirane Chemical compound C1OC1COC1=CC=CC=C1.C1OC1COC1=CC=CC=C1 GGZUSLXFZZJXNP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
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- NEYTXADIGVEHQD-UHFFFAOYSA-N 2-hydroxy-2-(prop-2-enoylamino)acetic acid Chemical compound OC(=O)C(O)NC(=O)C=C NEYTXADIGVEHQD-UHFFFAOYSA-N 0.000 description 1
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- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
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- FRQQKWGDKVGLFI-UHFFFAOYSA-N 2-methylundecane-2-thiol Chemical compound CCCCCCCCCC(C)(C)S FRQQKWGDKVGLFI-UHFFFAOYSA-N 0.000 description 1
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- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
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- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
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- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- SMPWDQQFZPIOGD-UPHRSURJSA-N bis(2-hydroxyethyl) (z)-but-2-enedioate Chemical compound OCCOC(=O)\C=C/C(=O)OCCO SMPWDQQFZPIOGD-UPHRSURJSA-N 0.000 description 1
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 229920000891 common polymer Polymers 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 235000010350 erythorbic acid Nutrition 0.000 description 1
- 239000004318 erythorbic acid Substances 0.000 description 1
- HDERJYVLTPVNRI-UHFFFAOYSA-N ethene;ethenyl acetate Chemical group C=C.CC(=O)OC=C HDERJYVLTPVNRI-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000009972 garment dyeing Methods 0.000 description 1
- 238000013023 gasketing Methods 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 229940026239 isoascorbic acid Drugs 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000011499 joint compound Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- JMSTYCQEPRPFBF-UHFFFAOYSA-N methyl 2-methoxy-2-(prop-2-enoylamino)acetate Chemical compound COC(=O)C(OC)NC(=O)C=C JMSTYCQEPRPFBF-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229940100996 sodium bisulfate Drugs 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 229940001474 sodium thiosulfate Drugs 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/062—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/856,789 US5900451A (en) | 1997-05-15 | 1997-05-15 | Collaidally stabilized butadiene emulsions |
| US08/856,789 | 1997-05-15 | ||
| PCT/US1998/009938 WO1998051720A1 (en) | 1997-05-15 | 1998-05-15 | Colloidally stabilized butadiene emulsions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2289458A1 true CA2289458A1 (en) | 1998-11-19 |
Family
ID=25324520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002289458A Abandoned CA2289458A1 (en) | 1997-05-15 | 1998-05-15 | Colloidally stabilized butadiene emulsions |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5900451A (enExample) |
| EP (1) | EP0984993B1 (enExample) |
| JP (1) | JP2001525875A (enExample) |
| AT (1) | ATE342290T1 (enExample) |
| AU (1) | AU737568B2 (enExample) |
| BR (1) | BR9809620A (enExample) |
| CA (1) | CA2289458A1 (enExample) |
| DE (1) | DE69836135T2 (enExample) |
| WO (1) | WO1998051720A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6127595A (en) * | 1998-04-22 | 2000-10-03 | Air Products And Chemicals, Inc. | Cover sheet lamination for absorbent article and low temperature lamination process |
| WO2000008077A1 (en) * | 1998-08-07 | 2000-02-17 | Reichhold, Inc. | Novel latex compositions for deposition on various substrates |
| US6599638B1 (en) | 1999-09-10 | 2003-07-29 | Dow Reichhold Specialty Latex Llc | Colloidally stabilized emulsions |
| DE60026882T2 (de) | 1999-12-21 | 2006-11-16 | Omnova Solutions Inc., Fairlawn | Polyvinylalkoholcopolymerzusammensetzung |
| US6673871B2 (en) | 2000-12-21 | 2004-01-06 | Kimberly-Clark Worldwide, Inc. | Elastomeric articles made from a synthetic polymer |
| DE10213026A1 (de) * | 2002-03-22 | 2003-10-02 | Basf Ag | Polymerdispersionen als Zusatz in Baumaterialien |
| JP2004182794A (ja) * | 2002-11-29 | 2004-07-02 | Nippon A & L Kk | 耐水接着剤用ラテックスおよび水性高分子イソシアネート系耐水接着剤 |
| JP4421840B2 (ja) * | 2003-05-02 | 2010-02-24 | 株式会社カネカ | 樹脂組成物及びその製造方法 |
| US6951250B2 (en) * | 2003-05-13 | 2005-10-04 | Halliburton Energy Services, Inc. | Sealant compositions and methods of using the same to isolate a subterranean zone from a disposal well |
| US7491753B2 (en) | 2003-07-03 | 2009-02-17 | Mallard Creek Polymers, Inc. | Antimicrobial and antistatic polymers and methods of using such polymers on various substrates |
| US7607483B2 (en) * | 2004-04-19 | 2009-10-27 | Halliburton Energy Services, Inc. | Sealant compositions comprising colloidally stabilized latex and methods of using the same |
| US7479519B2 (en) * | 2004-10-27 | 2009-01-20 | Mallard Creek Polymers, Inc. | Curable urethane polymer adhesives and coatings |
| US20070111900A1 (en) * | 2005-11-11 | 2007-05-17 | Reddy B R | Sealant compositions comprising solid latex |
| US7488705B2 (en) * | 2004-12-08 | 2009-02-10 | Halliburton Energy Services, Inc. | Oilwell sealant compositions comprising alkali swellable latex |
| US20070111901A1 (en) * | 2005-11-11 | 2007-05-17 | Reddy B R | Method of servicing a wellbore with a sealant composition comprising solid latex |
| US7267174B2 (en) * | 2005-01-24 | 2007-09-11 | Halliburton Energy Services, Inc. | Methods of plugging a permeable zone downhole using a sealant composition comprising a crosslinkable material and a reduced amount of cement |
| US20060167133A1 (en) * | 2005-01-24 | 2006-07-27 | Jan Gromsveld | Sealant composition comprising a crosslinkable material and a reduced amount of cement for a permeable zone downhole |
| US8703659B2 (en) | 2005-01-24 | 2014-04-22 | Halliburton Energy Services, Inc. | Sealant composition comprising a gel system and a reduced amount of cement for a permeable zone downhole |
| US20070048249A1 (en) | 2005-08-24 | 2007-03-01 | Purdue Research Foundation | Hydrophilized bactericidal polymers |
| US7576042B2 (en) * | 2006-02-28 | 2009-08-18 | Halliburton Energy Services, Inc. | Salt water stable latex cement slurries |
| RU2444541C2 (ru) | 2006-08-24 | 2012-03-10 | Маллард Крик Полимерс, Инк. | Катионный латекс в качестве носителя биоактивных ингредиентов и способы его получения и использования |
| EP2341084B1 (en) * | 2009-12-30 | 2015-02-25 | Dow Global Technologies LLC | Redispersible polymer powders stabilized with protective colloid compositions |
| EP2341083B1 (en) * | 2009-12-30 | 2015-07-08 | Dow Global Technologies LLC | Stabilized redispersible polymer powder compositions |
| CN105971579B (zh) * | 2016-07-07 | 2018-05-08 | 赵立强 | 一种相变水力压裂工艺 |
| WO2018222622A1 (en) | 2017-05-27 | 2018-12-06 | Poly Group LLC | Dispersible antimicrobial complex and coatings therefrom |
| EP3638740B1 (en) | 2017-06-16 | 2024-08-07 | Poly Group LLC | Polymeric antimicrobial surfactant |
| JP2021147553A (ja) * | 2020-03-23 | 2021-09-27 | 旭化成株式会社 | 共重合体ラテックス、水性接着剤組成物、及び積層体 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1100958B (de) * | 1959-08-01 | 1961-03-02 | Hoechst Ag | Verfahren zur Herstellung von Polymerisat-Dispersionen |
| US3365408A (en) * | 1963-08-12 | 1968-01-23 | Kurashiki Rayon Co | Adhesives comprising polyvinyl alcohol bearing or mixed with substances bearing carboxyl groups, and a stabilizer |
| JPS5819475B2 (ja) * | 1975-11-28 | 1983-04-18 | 住友ノ−ガタック株式会社 | 感圧複写紙用呈色紙 |
| JPS5839161B2 (ja) * | 1976-08-03 | 1983-08-27 | 大日本インキ化学工業株式会社 | 分散樹脂組成物の製造法 |
| DE2842719A1 (de) * | 1978-09-30 | 1980-04-10 | Basf Ag | Verfahren zur herstellung von waessrigen polyacrylat-dispersionen mit verbessertem fliessverhalten |
| DE2926631A1 (de) * | 1979-07-02 | 1981-01-29 | Wacker Chemie Gmbh | Waessrige dispersion auf grundlage von (meth-)acrylsaeurederivaten, ihre herstellung und verwendung |
| JPS57180617A (en) * | 1981-05-01 | 1982-11-06 | Japan Synthetic Rubber Co Ltd | Copolymer latex for chipping-resistant paint |
| US4417016A (en) * | 1982-02-19 | 1983-11-22 | Para-Chem Southern, Inc. | Frothing aid composition |
| US4384661A (en) * | 1982-04-07 | 1983-05-24 | Page Edward H | Aerosol water-based paint compositions |
| US4477613A (en) * | 1983-08-01 | 1984-10-16 | Sylvachem Corporation | Stabilization of tackifying resin dispersions |
| CA1272339A (en) * | 1984-06-25 | 1990-07-31 | Paul James Mollinger | Process for pelletization of powder materials and products therefrom |
| US4834096A (en) * | 1987-10-26 | 1989-05-30 | Edward Weck Incorporated | Plastic ligating clips |
| EP0422120A4 (en) * | 1988-06-20 | 1991-08-21 | Ppg Industries, Inc. | Polymerizable surfactant |
| US5296627A (en) * | 1988-06-20 | 1994-03-22 | Ppg Industries, Inc. | Ethylenically unsaturated poly(alkyleneoxy) surfactants |
| CN1092430A (zh) * | 1989-10-25 | 1994-09-21 | 陶氏化学公司 | 纸张涂料组合物用的胶乳共聚物 |
| US5200459A (en) * | 1991-05-31 | 1993-04-06 | Lord Corporation | Stable butadiene heteropolymer latices |
| US5539015A (en) * | 1991-07-25 | 1996-07-23 | Kabushiki Kaisha Toyota Chuo Kenkyusho | Synthetic resin composition and interior material coated with the same |
| US5378759A (en) * | 1992-04-23 | 1995-01-03 | Rohm And Haas Company | Polymer blends |
| US5428095A (en) * | 1992-06-09 | 1995-06-27 | Cal-West Automotive | Protective coating composition and method of using such composition |
| CA2110448A1 (en) * | 1992-12-08 | 1994-06-09 | Helen H.Y. Pak-Harvey | Redispersible acrylic polymer powder for cementitious compositions |
| US5403640A (en) * | 1993-08-27 | 1995-04-04 | Reichhold Chemicals, Inc. | Textile coating and method of using the same |
| CA2130616A1 (en) * | 1993-08-27 | 1995-02-28 | Mark Charles Bricker | Polymer emulsion, agent for cross-linking a polymer emulsion and method for making a polymer film |
| US5496884A (en) * | 1993-11-12 | 1996-03-05 | Lord Corporation | Aqueous adhesive for bonding elastomers |
| US5461104A (en) * | 1994-01-21 | 1995-10-24 | Shell Oil Company | Process for making water-based latexes of block copolymers |
| US5444112A (en) * | 1994-05-16 | 1995-08-22 | Cj's Distributing, Inc. | Sprayable nonionic neoprene latex adhesive and method of preparation |
| US5629370A (en) * | 1996-04-29 | 1997-05-13 | Reichhold Chemicals, Inc. | High solids vinyl acetate-ethylene emulsions |
-
1997
- 1997-05-15 US US08/856,789 patent/US5900451A/en not_active Expired - Lifetime
-
1998
- 1998-05-15 WO PCT/US1998/009938 patent/WO1998051720A1/en not_active Ceased
- 1998-05-15 AT AT98921221T patent/ATE342290T1/de not_active IP Right Cessation
- 1998-05-15 BR BR9809620-6A patent/BR9809620A/pt unknown
- 1998-05-15 AU AU73882/98A patent/AU737568B2/en not_active Ceased
- 1998-05-15 CA CA002289458A patent/CA2289458A1/en not_active Abandoned
- 1998-05-15 EP EP98921221A patent/EP0984993B1/en not_active Expired - Lifetime
- 1998-05-15 DE DE69836135T patent/DE69836135T2/de not_active Expired - Lifetime
- 1998-05-15 JP JP54956498A patent/JP2001525875A/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP0984993B1 (en) | 2006-10-11 |
| BR9809620A (pt) | 2000-07-04 |
| ATE342290T1 (de) | 2006-11-15 |
| AU737568B2 (en) | 2001-08-23 |
| DE69836135D1 (de) | 2006-11-23 |
| DE69836135T2 (de) | 2007-08-23 |
| AU7388298A (en) | 1998-12-08 |
| JP2001525875A (ja) | 2001-12-11 |
| EP0984993A1 (en) | 2000-03-15 |
| US5900451A (en) | 1999-05-04 |
| WO1998051720A1 (en) | 1998-11-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |