EP0563291A4 - - Google Patents
Info
- Publication number
- EP0563291A4 EP0563291A4 EP19920903541 EP92903541A EP0563291A4 EP 0563291 A4 EP0563291 A4 EP 0563291A4 EP 19920903541 EP19920903541 EP 19920903541 EP 92903541 A EP92903541 A EP 92903541A EP 0563291 A4 EP0563291 A4 EP 0563291A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- transition metal
- thermoplastic
- metal compound
- present
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 claims abstract description 50
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 31
- -1 polyethylene, ethylene copolymers Polymers 0.000 claims abstract description 25
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 18
- 150000003623 transition metal compounds Chemical class 0.000 claims abstract description 15
- 150000008365 aromatic ketones Chemical class 0.000 claims abstract description 10
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000012965 benzophenone Substances 0.000 claims abstract description 6
- JXSRRBVHLUJJFC-UHFFFAOYSA-N 7-amino-2-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile Chemical compound N1=CC(C#N)=C(N)N2N=C(SC)N=C21 JXSRRBVHLUJJFC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000004793 Polystyrene Substances 0.000 claims abstract description 5
- 230000009471 action Effects 0.000 claims abstract description 5
- FRVCGRDGKAINSV-UHFFFAOYSA-L iron(2+);octadecanoate Chemical compound [Fe+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O FRVCGRDGKAINSV-UHFFFAOYSA-L 0.000 claims abstract description 5
- 229920002223 polystyrene Polymers 0.000 claims abstract description 5
- 229920002635 polyurethane Polymers 0.000 claims abstract description 5
- 239000004814 polyurethane Substances 0.000 claims abstract description 5
- 239000004743 Polypropylene Substances 0.000 claims abstract description 4
- 150000001336 alkenes Chemical class 0.000 claims abstract description 4
- 229920001155 polypropylene Polymers 0.000 claims abstract description 4
- 229920000642 polymer Polymers 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 abstract description 9
- 150000003624 transition metals Chemical class 0.000 abstract description 9
- 150000002506 iron compounds Chemical class 0.000 abstract description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 17
- 239000012141 concentrate Substances 0.000 description 12
- 229920003023 plastic Polymers 0.000 description 12
- 239000004033 plastic Substances 0.000 description 12
- 239000000306 component Substances 0.000 description 9
- 239000003446 ligand Substances 0.000 description 9
- 239000004698 Polyethylene Substances 0.000 description 7
- 238000006731 degradation reaction Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 6
- 239000012815 thermoplastic material Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001782 photodegradation Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000006065 biodegradation reaction Methods 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- PEVZEFCZINKUCG-UHFFFAOYSA-L copper;octadecanoate Chemical compound [Cu+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O PEVZEFCZINKUCG-UHFFFAOYSA-L 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- 229940114069 12-hydroxystearate Drugs 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229920001038 ethylene copolymer Polymers 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- MPCGVMBDFHRSCF-UHFFFAOYSA-N (4-octylphenyl)-phenylmethanone Chemical compound C1=CC(CCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 MPCGVMBDFHRSCF-UHFFFAOYSA-N 0.000 description 1
- SEXKDZSOKXPFFH-UHFFFAOYSA-N 1-(2-benzoylphenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 SEXKDZSOKXPFFH-UHFFFAOYSA-N 0.000 description 1
- BLDFSDCBQJUWFG-UHFFFAOYSA-N 2-(methylamino)-1,2-diphenylethanol Chemical compound C=1C=CC=CC=1C(NC)C(O)C1=CC=CC=C1 BLDFSDCBQJUWFG-UHFFFAOYSA-N 0.000 description 1
- 241001137251 Corvidae Species 0.000 description 1
- 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 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- SHBUUTHKGIVMJT-UHFFFAOYSA-N Hydroxystearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OO SHBUUTHKGIVMJT-UHFFFAOYSA-N 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical group O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000001217 buttock Anatomy 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 229920005648 ethylene methacrylic acid copolymer Polymers 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229940072106 hydroxystearate Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- WKPSFPXMYGFAQW-UHFFFAOYSA-N iron;hydrate Chemical compound O.[Fe] WKPSFPXMYGFAQW-UHFFFAOYSA-N 0.000 description 1
- 229920000092 linear low density polyethylene Polymers 0.000 description 1
- 239000004707 linear low-density polyethylene Substances 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229920001179 medium density polyethylene Polymers 0.000 description 1
- 239000004701 medium-density polyethylene Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000012476 oxidizable substance Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 235000015108 pies Nutrition 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000013502 plastic waste Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 239000002699 waste material Substances 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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/50—Partial depolymerisation
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0033—Additives activating the degradation of the macromolecular compound
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
Definitions
- Fig. 1 is a graph illustrating loss of elonga ⁇ tion at break as a function of time in a plastic film product including the composition of the pre ⁇ - ent invention.
- composition of the present invention may be formed in any of the following manners.
- the compo ⁇ sition may be added directly at the final production stage by the manufacturer, formed in a concentrate and supplied to the manufacturer to be added to the base resin or formed with the base resin and supplied to the manufacturer ready for use.
- the first transition metal component preferably comprises an iron compound generally having the for ⁇ mula X-Fe, where X represents one or more ligands.
- the compound may additionally be coupled to a fur ⁇ ther ligand Y.
- Fe may designate iron in any known valancy.
- the ligand X may be an inorganic or organic acid radical or likewise another ligand bonded in a complex.
- suitable ligands X include OH-, C1-, Br-, I-, oxalate-, H-citrate-, NO- , N-.- EDTA or a carbonyl, nitrosyl or porphyrin radical.
- Suitable ligands Y include carboxylic acid ions of aromatic or aliphatic monocarboxylic acid or of dicarboxylic acids, the aliphatic carboxylic acid preferably having 10 to 20 carbon atoms.
- Ligand Y serves in general to increase the solubility of the compound X-Fe in the polymer.
- the iron compound more preferably is comprised of iron stearate pres ⁇ ent in the final concentration of the present inven ⁇ tion in an amount from about 0.01 weight percent to about 0.5 weight percent, and more preferably in an amount from about 0.1 weight percent to about 0.3 weight percent. It is understood that the ranges listed herein are for purposes of illustration.
- thermoplastic composition of the present invention formed in a concentrate wherein the compositional ranges of the various components are by weight percent of the total concentrate.
- thermoplastic composition of the present invention formed in a concentrate wherein the compositional ranges of the various components are by weight percent of the total concentrate.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63236290A | 1990-12-21 | 1990-12-21 | |
| US632362 | 1990-12-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0563291A1 EP0563291A1 (en) | 1993-10-06 |
| EP0563291A4 true EP0563291A4 (enrdf_load_stackoverflow) | 1994-04-13 |
Family
ID=24535226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP92903541A Withdrawn EP0563291A1 (en) | 1990-12-21 | 1991-12-20 | Photodegradable plastic composition |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0563291A1 (enrdf_load_stackoverflow) |
| JP (1) | JP3184886B2 (enrdf_load_stackoverflow) |
| KR (1) | KR930703370A (enrdf_load_stackoverflow) |
| CA (1) | CA2098911A1 (enrdf_load_stackoverflow) |
| WO (1) | WO1992011298A1 (enrdf_load_stackoverflow) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5658780A (en) | 1992-12-07 | 1997-08-19 | Ribozyme Pharmaceuticals, Inc. | Rel a targeted ribozymes |
| ES2127948T3 (es) * | 1993-10-27 | 1999-05-01 | Ribozyme Pharm Inc | Oligonucleotidos modificados en la posicion 2'-amido y 2'-peptido. |
| US5814404A (en) * | 1994-06-03 | 1998-09-29 | Minnesota Mining And Manufacturing Company | Degradable multilayer melt blown microfibers |
| US6214915B1 (en) * | 1998-12-10 | 2001-04-10 | General Electric Company | Stabilized thermoplastic compositions |
| US6482872B2 (en) | 1999-04-01 | 2002-11-19 | Programmable Materials, Inc. | Process for manufacturing a biodegradable polymeric composition |
| ITMI20021711A1 (it) * | 2002-07-31 | 2004-02-01 | Polimeri Europa Spa | Polimeri vinilaromatici espandibili in perle e procedimento per la loro preparazione. |
| NO324368B1 (no) * | 2003-04-23 | 2007-10-01 | Normors As | Fremgangsmate for fremstilling av tilsetningsmiddel til termoplaster og slik fremstilt tilsetningsmiddel samt termoplast inneholdende slikt tilsetningsmiddel. |
| WO2007027163A2 (en) * | 2005-09-01 | 2007-03-08 | Super Film Ambalaj Sanayi Ve Ticaret A. S. | Degradable biodegradable polypropylene film |
| WO2007028731A1 (en) * | 2005-09-07 | 2007-03-15 | Ciba Specialty Chemicals Holding Inc. | A degradable polymer article |
| BRPI0813862A2 (pt) * | 2007-08-02 | 2017-06-06 | Basf Se | método para melhorar a degradação de polímeros naturais e/ou sintéticos ou um artigo polimérico, composto, e, artigo polimérico |
| FR2943219B1 (fr) * | 2009-03-20 | 2012-05-18 | Polytek Innovations | Produit a usage agricole et son procede de fabrication |
| JP5484161B2 (ja) | 2010-03-31 | 2014-05-07 | 小林製薬株式会社 | 生分解性使い捨てカイロ |
| CN103172981B (zh) * | 2011-12-21 | 2017-03-01 | 香港生产力促进局 | 一种可降解聚合物组合物及其制备方法 |
| CN107001998B (zh) * | 2014-11-18 | 2020-07-24 | 日油株式会社 | 铁皂、其制备方法及含有该铁皂的热塑性树脂组合物 |
| CN106032422A (zh) * | 2015-03-13 | 2016-10-19 | 香港纺织及成衣研发中心有限公司 | 一种可降解合成纤维组合物及其制备方法和制品 |
| JP7105242B2 (ja) | 2016-11-22 | 2022-07-22 | ポリマテリア・リミテッド | 分解性ポリマーおよび製造方法 |
| CN111393738B (zh) * | 2020-05-06 | 2022-12-02 | 江苏祎唯诺新材料科技有限公司 | 一种光降解型pe缠绕膜及其制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2200299A1 (enrdf_load_stackoverflow) * | 1972-09-20 | 1974-04-19 | Huels Chemische Werke Ag |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1346650A (en) * | 1970-09-18 | 1974-02-13 | Sekisui Chemical Co Ltd | Photo-degradable resin compositions |
| US3941759A (en) * | 1972-03-01 | 1976-03-02 | Owens-Illinois, Inc. | Degradable plastics containing dual-function additive system |
| US3981856A (en) * | 1974-03-07 | 1976-09-21 | Princeton Polymer Laboratories, Incorporated | Degradable hydrocarbon polymers containing a metal compound and a benzotriazole |
-
1991
- 1991-12-20 JP JP50375992A patent/JP3184886B2/ja not_active Expired - Fee Related
- 1991-12-20 CA CA002098911A patent/CA2098911A1/en not_active Abandoned
- 1991-12-20 EP EP92903541A patent/EP0563291A1/en not_active Withdrawn
- 1991-12-20 WO PCT/US1991/009731 patent/WO1992011298A1/en not_active Application Discontinuation
- 1991-12-20 KR KR1019930701906A patent/KR930703370A/ko not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2200299A1 (enrdf_load_stackoverflow) * | 1972-09-20 | 1974-04-19 | Huels Chemische Werke Ag |
Non-Patent Citations (3)
| Title |
|---|
| CHEMICAL ABSTRACTS, vol. 78, no. 12, 26 March 1973, Columbus, Ohio, US; abstract no. 73161y, YASUNO, KIYOSHI: "PHOTODEGRADABLE RESIN COMPOSITIONS" page 42; column 1; * |
| CHEMICAL ABSTRACTS, vol. 80, no. 20, 20 May 1974, Columbus, Ohio, US; abstract no. 109391f, TSUJI, KOJO: "PHOTODEGRADABLE POLYETHYLENE COMPOSITIONS" page 39; column 2; * |
| See also references of WO9211298A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0563291A1 (en) | 1993-10-06 |
| KR930703370A (ko) | 1993-11-29 |
| WO1992011298A1 (en) | 1992-07-09 |
| JPH06504079A (ja) | 1994-05-12 |
| JP3184886B2 (ja) | 2001-07-09 |
| CA2098911A1 (en) | 1992-06-22 |
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