SE506467C2 - Förfarande för framställning av stabiliserad kolofonium och dess användning som klibbgivarharts i bindemedel - Google Patents
Förfarande för framställning av stabiliserad kolofonium och dess användning som klibbgivarharts i bindemedelInfo
- Publication number
- SE506467C2 SE506467C2 SE9102015A SE9102015A SE506467C2 SE 506467 C2 SE506467 C2 SE 506467C2 SE 9102015 A SE9102015 A SE 9102015A SE 9102015 A SE9102015 A SE 9102015A SE 506467 C2 SE506467 C2 SE 506467C2
- Authority
- SE
- Sweden
- Prior art keywords
- rosin
- iodine
- acid
- stabilized
- phosphoric acid
- Prior art date
Links
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims abstract description 93
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 title claims abstract description 86
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 title claims abstract description 86
- 238000000034 method Methods 0.000 title claims abstract description 20
- 229920005989 resin Polymers 0.000 title claims abstract description 18
- 239000011347 resin Substances 0.000 title claims abstract description 18
- 239000011230 binding agent Substances 0.000 title claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 40
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000011630 iodine Substances 0.000 claims abstract description 32
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 32
- 238000004513 sizing Methods 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 20
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 11
- 239000010452 phosphate Substances 0.000 claims abstract description 11
- 238000007323 disproportionation reaction Methods 0.000 claims abstract description 9
- 239000000853 adhesive Substances 0.000 claims abstract description 5
- 230000001070 adhesive effect Effects 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 239000006185 dispersion Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 17
- UXBFAGQTUAMQSX-PKUWUEBNSA-N (1R)-1,3-dimethyl-2-[2-(3-propan-2-ylphenyl)ethyl]cyclohexane-1-carboxylic acid Chemical compound CC(C)c1cccc(CCC2C(C)CCC[C@@]2(C)C(O)=O)c1 UXBFAGQTUAMQSX-PKUWUEBNSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- QUUCYKKMFLJLFS-UHFFFAOYSA-N Dehydroabietan Natural products CC1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 QUUCYKKMFLJLFS-UHFFFAOYSA-N 0.000 claims description 8
- NFWKVWVWBFBAOV-UHFFFAOYSA-N Dehydroabietic acid Natural products OC(=O)C1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 NFWKVWVWBFBAOV-UHFFFAOYSA-N 0.000 claims description 8
- NFWKVWVWBFBAOV-MISYRCLQSA-N dehydroabietic acid Chemical compound OC(=O)[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 NFWKVWVWBFBAOV-MISYRCLQSA-N 0.000 claims description 8
- 229940118781 dehydroabietic acid Drugs 0.000 claims description 8
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 claims description 6
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 239000000123 paper Substances 0.000 abstract description 14
- 239000011087 paperboard Substances 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
- 238000004026 adhesive bonding Methods 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940037003 alum Drugs 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- -1 stump Natural products 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 238000003490 calendering Methods 0.000 description 2
- 239000011436 cob Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- 229920005789 ACRONAL® acrylic binder Polymers 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/62—Rosin; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J201/00—Adhesives based on unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/26—Natural polymers, natural resins or derivatives thereof according to C08L1/00 - C08L5/00, C08L89/00, C08L93/00, C08L97/00 or C08L99/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paper (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catching Or Destruction (AREA)
- Pens And Brushes (AREA)
- Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)
- Lubricants (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9102015A SE506467C2 (sv) | 1991-06-28 | 1991-06-28 | Förfarande för framställning av stabiliserad kolofonium och dess användning som klibbgivarharts i bindemedel |
| US07/727,457 US5175250A (en) | 1991-06-28 | 1991-07-09 | Stabilized rosin and process for production and use thereof |
| AT92201700T ATE159750T1 (de) | 1991-06-28 | 1992-06-11 | Stabilisiertes kolophonium, verfahren zu seiner herstellung und verwendung desselben |
| DE69222891T DE69222891T2 (de) | 1991-06-28 | 1992-06-11 | Stabilisiertes Kolophonium, Verfahren zu seiner Herstellung und Verwendung desselben |
| EP92201700A EP0520541B1 (en) | 1991-06-28 | 1992-06-11 | Stabilized rosin and process for production and use thereof |
| CA002071750A CA2071750C (en) | 1991-06-28 | 1992-06-22 | Stabilized rosin and process for production and use thereof |
| AU18519/92A AU650146B2 (en) | 1991-06-28 | 1992-06-23 | Stabilized rosin and process for production and use thereof |
| NZ243268A NZ243268A (en) | 1991-06-28 | 1992-06-23 | Process for the production of stabilised rosin comprising heating with a strong acid and a phosphate and then disproportionating with iodine; use in adhesives and aqueous sizing dispersions |
| FI922941A FI106725B (fi) | 1991-06-28 | 1992-06-24 | Stabiloitu kolofoni, menetelmä sen valmistamiseksi ja sen käyttö |
| NO922536A NO303397B1 (no) | 1991-06-28 | 1992-06-26 | Stabilisert kolofoniumprodukt, fremgangsmÕte for fremstilling og anvendelse derav, samt klebemiddelblanding og vandig limningsdispersjon inneholdende det stabiliserte kolofonium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9102015A SE506467C2 (sv) | 1991-06-28 | 1991-06-28 | Förfarande för framställning av stabiliserad kolofonium och dess användning som klibbgivarharts i bindemedel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE9102015D0 SE9102015D0 (sv) | 1991-06-28 |
| SE9102015L SE9102015L (sv) | 1992-12-29 |
| SE506467C2 true SE506467C2 (sv) | 1997-12-22 |
Family
ID=20383194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE9102015A SE506467C2 (sv) | 1991-06-28 | 1991-06-28 | Förfarande för framställning av stabiliserad kolofonium och dess användning som klibbgivarharts i bindemedel |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5175250A (no) |
| EP (1) | EP0520541B1 (no) |
| AT (1) | ATE159750T1 (no) |
| AU (1) | AU650146B2 (no) |
| CA (1) | CA2071750C (no) |
| DE (1) | DE69222891T2 (no) |
| FI (1) | FI106725B (no) |
| NO (1) | NO303397B1 (no) |
| NZ (1) | NZ243268A (no) |
| SE (1) | SE506467C2 (no) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0572680B1 (en) * | 1991-12-21 | 1997-05-28 | Arakawa Kagaku Kogyo Kabushiki Kaisha | Process for producing rosin ester and colorless rosin |
| JP3371982B2 (ja) * | 1993-05-18 | 2003-01-27 | 荒川化学工業株式会社 | 無色ロジンの製造法 |
| DE4409239C2 (de) * | 1994-03-18 | 2003-01-23 | Henkel Kgaa | Additive zur Unterdrückung der Kristallisation von Harzsäuren |
| DE4409240A1 (de) * | 1994-03-18 | 1995-09-21 | Henkel Kgaa | Modifizierte Harze |
| US6087318A (en) * | 1998-10-19 | 2000-07-11 | Georgia-Pacific Resins, Inc. | Process to produce disproportionated rosin based emulsifier for emulsion polymerization |
| CN101115813A (zh) * | 2005-02-09 | 2008-01-30 | 雅宝公司 | 制备歧化松香的方法 |
| US7868066B2 (en) * | 2007-07-20 | 2011-01-11 | Ppg Industries Ohio, Inc. | Aqueous dispersions and coatings comprising modified epoxy resins comprising the reaction product of rosin and a dienophile |
| US8057592B2 (en) * | 2007-07-20 | 2011-11-15 | Ppg Industries Ohio, Inc. | Cationic electrodepositable coatings comprising rosin |
| US7812101B2 (en) | 2007-07-20 | 2010-10-12 | Ppg Industries Ohio, Inc. | Modified epoxy resins comprising the reaction product of a biomass derived compound and an epoxy resin, and aqueous dispersions and coatings comprising such resins |
| US8039551B2 (en) * | 2007-07-20 | 2011-10-18 | Ppg Industries Ohio, Inc. | Modified epoxy resins comprising the reaction product of rosin and a linking molecule and aqueous dispersions and coatings comprising such resins |
| EP2039732A1 (en) * | 2007-09-20 | 2009-03-25 | Hexion Specialty Chemicals Research Belgium S.A. | Waterbased dimerized rosins and the process to make them |
| DE102012207801A1 (de) | 2012-05-10 | 2013-11-14 | Wacker Chemie Ag | Verwendung von Copolymerisaten als Klebrigmacher für Klebstoffe |
| CN106867409A (zh) * | 2017-03-29 | 2017-06-20 | 南宁市青秀区嘉利林化有限公司 | 一种松香复合抗氧化剂 |
| CN109777301B (zh) * | 2019-02-27 | 2021-03-30 | 广西创跃化工有限公司 | 歧化松香的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1426063A (fr) * | 1962-02-23 | 1966-01-28 | Anciens Etablissements Granel | Traitement de colophane |
| NL6609081A (no) * | 1964-07-13 | 1968-01-02 | ||
| FR1425589A (fr) * | 1965-01-06 | 1966-01-24 | Procédé de fabrication de colophanes disproportionnées, installation pour la miseen oeuvre du procédé et produits conformes à ceux obtenus par le présent procédé ou procédé similaire | |
| US3663523A (en) * | 1969-10-30 | 1972-05-16 | Us Agriculture | Dicarboxylic acid from rosin and process for preparing same |
| US3872073A (en) * | 1973-05-21 | 1975-03-18 | Arizona Chem | Process for the preparation of crystallization-resistant disproportionated rosin |
| JPS57165499A (en) * | 1981-04-03 | 1982-10-12 | Harima Chemicals Inc | Manufacture of decolored asymmetrized rosin soap |
| EP0074544B2 (en) * | 1981-09-15 | 1991-12-27 | Hercules Incorporated | Aqueous sizing compositions |
| SE465833B (sv) * | 1987-01-09 | 1991-11-04 | Eka Nobel Ab | Vattenhaltig dispersion innehaallande en blandning av hydrofoberande kolofoniummaterial och syntetiskt hydrofoberingsmedel, saett foer framstaellning av dispersionen samt anvaendning av dispersionen vid framstaellning av papper och liknande produkter |
-
1991
- 1991-06-28 SE SE9102015A patent/SE506467C2/sv not_active IP Right Cessation
- 1991-07-09 US US07/727,457 patent/US5175250A/en not_active Expired - Lifetime
-
1992
- 1992-06-11 EP EP92201700A patent/EP0520541B1/en not_active Expired - Lifetime
- 1992-06-11 DE DE69222891T patent/DE69222891T2/de not_active Expired - Lifetime
- 1992-06-11 AT AT92201700T patent/ATE159750T1/de not_active IP Right Cessation
- 1992-06-22 CA CA002071750A patent/CA2071750C/en not_active Expired - Lifetime
- 1992-06-23 AU AU18519/92A patent/AU650146B2/en not_active Ceased
- 1992-06-23 NZ NZ243268A patent/NZ243268A/en not_active IP Right Cessation
- 1992-06-24 FI FI922941A patent/FI106725B/fi not_active IP Right Cessation
- 1992-06-26 NO NO922536A patent/NO303397B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI922941A (fi) | 1992-12-29 |
| NO303397B1 (no) | 1998-07-06 |
| CA2071750C (en) | 1999-10-05 |
| AU650146B2 (en) | 1994-06-09 |
| ATE159750T1 (de) | 1997-11-15 |
| FI922941A0 (fi) | 1992-06-24 |
| EP0520541A3 (en) | 1994-08-24 |
| NZ243268A (en) | 1994-09-27 |
| EP0520541B1 (en) | 1997-10-29 |
| NO922536D0 (no) | 1992-06-26 |
| SE9102015D0 (sv) | 1991-06-28 |
| DE69222891T2 (de) | 1998-04-09 |
| NO922536L (no) | 1992-12-29 |
| FI106725B (fi) | 2001-03-30 |
| SE9102015L (sv) | 1992-12-29 |
| US5175250A (en) | 1992-12-29 |
| CA2071750A1 (en) | 1992-12-29 |
| EP0520541A2 (en) | 1992-12-30 |
| DE69222891D1 (de) | 1997-12-04 |
| AU1851992A (en) | 1993-01-21 |
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