TWI257399B - Improved cellular plastic material and method of making the same - Google Patents
Improved cellular plastic material and method of making the sameInfo
- Publication number
- TWI257399B TWI257399B TW089104795A TW89104795A TWI257399B TW I257399 B TWI257399 B TW I257399B TW 089104795 A TW089104795 A TW 089104795A TW 89104795 A TW89104795 A TW 89104795A TW I257399 B TWI257399 B TW I257399B
- Authority
- TW
- Taiwan
- Prior art keywords
- vegetable oil
- aforementioned
- diisocyanate
- substance
- oil
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims abstract description 72
- 239000004033 plastic Substances 0.000 title claims abstract description 14
- 229920003023 plastic Polymers 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title abstract description 9
- 230000001413 cellular effect Effects 0.000 title abstract 3
- 239000006260 foam Substances 0.000 claims abstract description 101
- 239000008158 vegetable oil Substances 0.000 claims abstract description 99
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 98
- 239000012948 isocyanate Substances 0.000 claims abstract description 55
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 54
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 37
- 229920005862 polyol Polymers 0.000 claims abstract description 33
- 229920001971 elastomer Polymers 0.000 claims abstract description 24
- 239000000806 elastomer Substances 0.000 claims abstract description 23
- 150000003077 polyols Chemical class 0.000 claims abstract description 23
- 239000003921 oil Substances 0.000 claims abstract description 14
- 235000019198 oils Nutrition 0.000 claims abstract description 14
- 239000004971 Cross linker Substances 0.000 claims abstract description 9
- 239000007787 solid Substances 0.000 claims abstract description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 162
- 239000003054 catalyst Substances 0.000 claims description 119
- 239000003549 soybean oil Substances 0.000 claims description 102
- 235000012424 soybean oil Nutrition 0.000 claims description 102
- 239000003431 cross linking reagent Substances 0.000 claims description 93
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 239000000126 substance Substances 0.000 claims description 61
- 239000011148 porous material Substances 0.000 claims description 54
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 48
- 125000005442 diisocyanate group Chemical group 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 42
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 41
- 150000002431 hydrogen Chemical class 0.000 claims description 39
- -1 methyl 2,4 diisocyanate Chemical compound 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 150000005846 sugar alcohols Polymers 0.000 claims description 36
- 239000004604 Blowing Agent Substances 0.000 claims description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 33
- 239000003208 petroleum Substances 0.000 claims description 32
- 238000005187 foaming Methods 0.000 claims description 24
- 239000007789 gas Substances 0.000 claims description 22
- 239000004088 foaming agent Substances 0.000 claims description 21
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 20
- 239000002984 plastic foam Substances 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 238000009835 boiling Methods 0.000 claims description 16
- 239000012970 tertiary amine catalyst Substances 0.000 claims description 15
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 14
- 239000004202 carbamide Substances 0.000 claims description 14
- 150000003512 tertiary amines Chemical group 0.000 claims description 14
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 13
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 12
- 238000004132 cross linking Methods 0.000 claims description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 235000019482 Palm oil Nutrition 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 230000002079 cooperative effect Effects 0.000 claims description 10
- 239000002540 palm oil Substances 0.000 claims description 10
- 235000012343 cottonseed oil Nutrition 0.000 claims description 9
- 239000002385 cottonseed oil Substances 0.000 claims description 9
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 235000010469 Glycine max Nutrition 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 6
- 238000007086 side reaction Methods 0.000 claims description 6
- 235000013311 vegetables Nutrition 0.000 claims description 6
- 244000068988 Glycine max Species 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 4
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 239000000828 canola oil Substances 0.000 claims description 3
- 235000019519 canola oil Nutrition 0.000 claims description 3
- KKCOQCVPBASEDD-UHFFFAOYSA-N 1-cyclooctyl-1,4-diazocane Chemical group C1CCCCCCC1N1CCNCCCC1 KKCOQCVPBASEDD-UHFFFAOYSA-N 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims 28
- 230000001276 controlling effect Effects 0.000 claims 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 8
- 239000004814 polyurethane Substances 0.000 claims 8
- 241001262968 Eunice Species 0.000 claims 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 5
- 229910052707 ruthenium Inorganic materials 0.000 claims 5
- WRBBSIGKIBSIBT-UHFFFAOYSA-N CCCCC(CCCC)(C1=CC=CC=C1)C1=CC=CC=C1.N=C=O.N=C=O Chemical compound CCCCC(CCCC)(C1=CC=CC=C1)C1=CC=CC=C1.N=C=O.N=C=O WRBBSIGKIBSIBT-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 230000000704 physical effect Effects 0.000 claims 3
- 229920002635 polyurethane Polymers 0.000 claims 3
- 240000002791 Brassica napus Species 0.000 claims 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 210000002784 stomach Anatomy 0.000 claims 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 1
- NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 claims 1
- YBQZXXMEJHZYMB-UHFFFAOYSA-N 1,2-diphenylhydrazine Chemical compound C=1C=CC=CC=1NNC1=CC=CC=C1 YBQZXXMEJHZYMB-UHFFFAOYSA-N 0.000 claims 1
- OMRJSCBKLPEXFV-UHFFFAOYSA-N 3-methylbutanethioic s-acid Chemical compound CC(C)CC(S)=O OMRJSCBKLPEXFV-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 150000000703 Cerium Chemical class 0.000 claims 1
- 229920000742 Cotton Polymers 0.000 claims 1
- 241000410536 Esme Species 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
- ZTCFKBWDKVMLMM-UHFFFAOYSA-N N=C=O.N=C=O.C=1C=CC=CC=1C(=O)C1=CC=CC=C1 Chemical compound N=C=O.N=C=O.C=1C=CC=CC=1C(=O)C1=CC=CC=C1 ZTCFKBWDKVMLMM-UHFFFAOYSA-N 0.000 claims 1
- 240000006394 Sorghum bicolor Species 0.000 claims 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims 1
- 241000270666 Testudines Species 0.000 claims 1
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
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- 150000001913 cyanates Chemical class 0.000 claims 1
- 210000005069 ears Anatomy 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- KCWDJXPPZHMEIK-UHFFFAOYSA-N isocyanic acid;toluene Chemical compound N=C=O.N=C=O.CC1=CC=CC=C1 KCWDJXPPZHMEIK-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000003642 reactive oxygen metabolite Substances 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 27
- 150000003673 urethanes Chemical class 0.000 abstract description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 71
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- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- RBWFXUOHBJGAMO-UHFFFAOYSA-N sulfanylidenebismuth Chemical compound [Bi]=S RBWFXUOHBJGAMO-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- 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
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0014—Use of organic additives
- C08J9/0023—Use of organic additives containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0008—Foam properties flexible
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Laminated Bodies (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Materials For Medical Uses (AREA)
- Massaging Devices (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/154,340 US6180686B1 (en) | 1998-09-17 | 1998-09-17 | Cellular plastic material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI257399B true TWI257399B (en) | 2006-07-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089104795A TWI257399B (en) | 1998-09-17 | 2000-05-15 | Improved cellular plastic material and method of making the same |
Country Status (16)
| Country | Link |
|---|---|
| US (8) | US6180686B1 (https=) |
| EP (1) | EP1127086B2 (https=) |
| JP (1) | JP2002524627A (https=) |
| CN (1) | CN1245428C (https=) |
| AT (1) | ATE286929T1 (https=) |
| AU (1) | AU766760B2 (https=) |
| BR (1) | BR9913784B1 (https=) |
| CA (1) | CA2344378C (https=) |
| DE (1) | DE69923210T3 (https=) |
| DK (1) | DK1127086T4 (https=) |
| ES (1) | ES2235516T5 (https=) |
| GT (1) | GT200000029A (https=) |
| MX (1) | MXPA01002680A (https=) |
| PT (1) | PT1127086E (https=) |
| TW (1) | TWI257399B (https=) |
| WO (1) | WO2000015684A1 (https=) |
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- 1999-09-17 DE DE69923210T patent/DE69923210T3/de not_active Expired - Lifetime
-
2000
- 2000-03-16 GT GT200000029A patent/GT200000029A/es unknown
- 2000-05-15 TW TW089104795A patent/TWI257399B/zh not_active IP Right Cessation
-
2002
- 2002-09-24 US US10/253,252 patent/US6624244B2/en not_active Expired - Fee Related
-
2003
- 2003-08-04 US US10/634,026 patent/US6864296B2/en not_active Expired - Fee Related
- 2003-08-12 US US10/639,109 patent/US6881763B2/en not_active Expired - Fee Related
- 2003-08-12 US US10/639,303 patent/US6867239B2/en not_active Expired - Fee Related
-
2005
- 2005-04-18 US US11/108,368 patent/US20050182228A1/en not_active Abandoned
-
2007
- 2007-10-31 US US11/933,049 patent/US20080051506A1/en not_active Abandoned
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| MM4A | Annulment or lapse of patent due to non-payment of fees |