CA2296678C - Methods and devices for measuring total polar compounds in degrading oils - Google Patents
Methods and devices for measuring total polar compounds in degrading oils Download PDFInfo
- Publication number
- CA2296678C CA2296678C CA002296678A CA2296678A CA2296678C CA 2296678 C CA2296678 C CA 2296678C CA 002296678 A CA002296678 A CA 002296678A CA 2296678 A CA2296678 A CA 2296678A CA 2296678 C CA2296678 C CA 2296678C
- Authority
- CA
- Canada
- Prior art keywords
- oil
- polar
- adsorbent
- sample
- indicator
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 95
- 239000003921 oil Substances 0.000 title claims description 278
- 238000000034 method Methods 0.000 title abstract description 37
- 230000000593 degrading effect Effects 0.000 title description 2
- 239000003463 adsorbent Substances 0.000 claims abstract description 111
- 238000012360 testing method Methods 0.000 claims abstract description 111
- 239000000463 material Substances 0.000 claims abstract description 13
- 235000019198 oils Nutrition 0.000 claims description 274
- 239000007787 solid Substances 0.000 claims description 35
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 30
- 229910052782 aluminium Inorganic materials 0.000 claims description 13
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 13
- 239000011521 glass Substances 0.000 claims description 10
- 235000019482 Palm oil Nutrition 0.000 claims description 9
- 239000004020 conductor Substances 0.000 claims description 9
- 239000002540 palm oil Substances 0.000 claims description 9
- 239000004033 plastic Substances 0.000 claims description 9
- 239000000377 silicon dioxide Substances 0.000 claims description 9
- 238000004891 communication Methods 0.000 claims description 8
- 239000012530 fluid Substances 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 6
- 241001677259 Acanthophoenix rubra Species 0.000 claims description 5
- 235000019483 Peanut oil Nutrition 0.000 claims description 5
- 239000002285 corn oil Substances 0.000 claims description 5
- 235000005687 corn oil Nutrition 0.000 claims description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 5
- 239000003346 palm kernel oil Substances 0.000 claims description 5
- 235000019865 palm kernel oil Nutrition 0.000 claims description 5
- 239000000312 peanut oil Substances 0.000 claims description 5
- 239000000828 canola oil Substances 0.000 claims description 4
- 235000019519 canola oil Nutrition 0.000 claims description 4
- 239000003240 coconut oil Substances 0.000 claims description 4
- 235000019864 coconut oil Nutrition 0.000 claims description 4
- 239000004006 olive oil Substances 0.000 claims description 4
- 235000008390 olive oil Nutrition 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 239000011135 tin Substances 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910001220 stainless steel Inorganic materials 0.000 claims description 2
- 239000010935 stainless steel Substances 0.000 claims description 2
- 230000002596 correlated effect Effects 0.000 abstract description 2
- 238000006073 displacement reaction Methods 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 27
- 239000002904 solvent Substances 0.000 description 14
- 239000012156 elution solvent Substances 0.000 description 11
- 230000033228 biological regulation Effects 0.000 description 9
- 235000013305 food Nutrition 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000015556 catabolic process Effects 0.000 description 7
- 239000003925 fat Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000004737 colorimetric analysis Methods 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 235000019197 fats Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 230000000875 corresponding effect Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 235000021588 free fatty acids Nutrition 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 239000001045 blue dye Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 235000013410 fast food Nutrition 0.000 description 4
- 239000011152 fibreglass Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000004904 shortening Methods 0.000 description 4
- -1 stainless Substances 0.000 description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- 241000287828 Gallus gallus Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000010411 cooking Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- 239000010913 used oil Substances 0.000 description 3
- 235000019871 vegetable fat Nutrition 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000008162 cooking oil Substances 0.000 description 2
- 230000003413 degradative effect Effects 0.000 description 2
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 235000012020 french fries Nutrition 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000275 quality assurance Methods 0.000 description 2
- 239000001044 red dye Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- DMDRBXCDTZRMHZ-UHFFFAOYSA-N 1,4-bis(2,4,6-trimethylanilino)anthracene-9,10-dione Chemical compound CC1=CC(C)=CC(C)=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=C(C)C=C(C)C=C1C DMDRBXCDTZRMHZ-UHFFFAOYSA-N 0.000 description 1
- DXWHZJXKTHGHQF-UHFFFAOYSA-N 2-butyl-6-(butylamino)benzo[de]isoquinoline-1,3-dione Chemical compound O=C1N(CCCC)C(=O)C2=CC=CC3=C2C1=CC=C3NCCCC DXWHZJXKTHGHQF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241001133760 Acoelorraphe Species 0.000 description 1
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 240000000385 Brassica napus var. napus Species 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- DBAKFASWICGISY-DASCVMRKSA-N Dexchlorpheniramine maleate Chemical compound OC(=O)\C=C/C(O)=O.C1([C@H](CCN(C)C)C=2N=CC=CC=2)=CC=C(Cl)C=C1 DBAKFASWICGISY-DASCVMRKSA-N 0.000 description 1
- 241000408529 Libra Species 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- VSYMNDBTCKIDLT-UHFFFAOYSA-N [2-(carbamoyloxymethyl)-2-ethylbutyl] carbamate Chemical compound NC(=O)OCC(CC)(CC)COC(N)=O VSYMNDBTCKIDLT-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000006652 catabolic pathway Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019688 fish Nutrition 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000021384 green leafy vegetables Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000021453 onion ring Nutrition 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000007793 ph indicator Substances 0.000 description 1
- 235000015108 pies Nutrition 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- TVRGPOFMYCMNRB-UHFFFAOYSA-N quinizarine green ss Chemical compound C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1 TVRGPOFMYCMNRB-UHFFFAOYSA-N 0.000 description 1
- 239000002824 redox indicator Substances 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000012883 sequential measurement Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/02—Food
- G01N33/03—Edible oils or edible fats
Landscapes
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating Or Analysing Materials By Optical Means (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1997/013168 WO1999005519A1 (en) | 1997-07-28 | 1997-07-28 | Methods and devices for measuring total polar compounds in degrading oils |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2296678A1 CA2296678A1 (en) | 1999-02-04 |
| CA2296678C true CA2296678C (en) | 2006-02-21 |
Family
ID=22261345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002296678A Expired - Fee Related CA2296678C (en) | 1997-07-28 | 1997-07-28 | Methods and devices for measuring total polar compounds in degrading oils |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1000353B1 (https=) |
| JP (1) | JP4149654B2 (https=) |
| KR (1) | KR100519881B1 (https=) |
| AT (1) | ATE310951T1 (https=) |
| AU (1) | AU750515B2 (https=) |
| CA (1) | CA2296678C (https=) |
| DE (1) | DE69734728T2 (https=) |
| ES (1) | ES2251031T3 (https=) |
| WO (1) | WO1999005519A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009111370A2 (en) * | 2008-03-04 | 2009-09-11 | 3M Innovative Properties Company | Monitoring of frying oil quality using combined optical interrogation methods and devices |
| US9782584B2 (en) | 2014-06-13 | 2017-10-10 | Nervana, LLC | Transcutaneous electrostimulator and methods for electric stimulation |
| WO2020092114A1 (en) * | 2018-10-29 | 2020-05-07 | Sorbent Technologies, Inc. | Development chambers for thin layer chromatography and methods of making and using the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2953439A (en) * | 1957-12-26 | 1960-09-20 | Allis Chalmers Mfg Co | Spot test method for estimating neutralization number of a mineral oil |
| US4349353A (en) * | 1981-09-25 | 1982-09-14 | Oil Process Systems, Inc. | Frying oil evaluator method and composition |
| NZ212374A (en) * | 1984-06-15 | 1988-04-29 | Oil Process Systems Inc | Process and kit for determination of polar substances in fat |
-
1997
- 1997-07-28 KR KR10-2000-7000926A patent/KR100519881B1/ko not_active Expired - Fee Related
- 1997-07-28 ES ES97935140T patent/ES2251031T3/es not_active Expired - Lifetime
- 1997-07-28 WO PCT/US1997/013168 patent/WO1999005519A1/en not_active Ceased
- 1997-07-28 DE DE69734728T patent/DE69734728T2/de not_active Expired - Fee Related
- 1997-07-28 AU AU38154/97A patent/AU750515B2/en not_active Ceased
- 1997-07-28 EP EP97935140A patent/EP1000353B1/en not_active Expired - Lifetime
- 1997-07-28 JP JP2000504454A patent/JP4149654B2/ja not_active Expired - Fee Related
- 1997-07-28 AT AT97935140T patent/ATE310951T1/de not_active IP Right Cessation
- 1997-07-28 CA CA002296678A patent/CA2296678C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE69734728D1 (de) | 2005-12-29 |
| CA2296678A1 (en) | 1999-02-04 |
| AU3815497A (en) | 1999-02-16 |
| ES2251031T3 (es) | 2006-04-16 |
| EP1000353B1 (en) | 2005-11-23 |
| EP1000353A1 (en) | 2000-05-17 |
| JP4149654B2 (ja) | 2008-09-10 |
| AU750515B2 (en) | 2002-07-18 |
| DE69734728T2 (de) | 2006-08-03 |
| ATE310951T1 (de) | 2005-12-15 |
| WO1999005519A1 (en) | 1999-02-04 |
| HK1028638A1 (en) | 2001-02-23 |
| KR20010022347A (ko) | 2001-03-15 |
| KR100519881B1 (ko) | 2005-10-11 |
| JP2001511523A (ja) | 2001-08-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |