DE69016124T2 - 1,3-Dialkylimidazol-2-thion-Katalysatoren enthaltende Überzugsmischungen. - Google Patents
1,3-Dialkylimidazol-2-thion-Katalysatoren enthaltende Überzugsmischungen.Info
- Publication number
- DE69016124T2 DE69016124T2 DE69016124T DE69016124T DE69016124T2 DE 69016124 T2 DE69016124 T2 DE 69016124T2 DE 69016124 T DE69016124 T DE 69016124T DE 69016124 T DE69016124 T DE 69016124T DE 69016124 T2 DE69016124 T2 DE 69016124T2
- Authority
- DE
- Germany
- Prior art keywords
- thione
- compound
- coating composition
- anhydride
- epoxy
- 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
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- 239000004593 Epoxy Substances 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims description 28
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- ZOCYDPURIYTNMU-UHFFFAOYSA-N 1-methyl-3-propylimidazole-2-thione Chemical compound CCCN1C=CN(C)C1=S ZOCYDPURIYTNMU-UHFFFAOYSA-N 0.000 claims description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
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- 241001061127 Thione Species 0.000 description 6
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- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
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- 239000005864 Sulphur Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- FLPKSBDJMLUTEX-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) 2-butyl-2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]propanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)(CCCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FLPKSBDJMLUTEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- AIFUAOGGAQPJFZ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;oxiran-2-ylmethyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.CCCCOC(=O)C=C.CC(=C)C(=O)OCC1CO1 AIFUAOGGAQPJFZ-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007590 electrostatic spraying Methods 0.000 description 1
- 229960003399 estrone Drugs 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 229940093470 ethylene Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000479 mixture part Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N propyl ethylene Natural products CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
Classifications
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/687—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing sulfur
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/39—Thiocarbamic acids; Derivatives thereof, e.g. dithiocarbamates
- C08K5/405—Thioureas; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Paints Or Removers (AREA)
- Epoxy Resins (AREA)
- Catalysts (AREA)
Claims (10)
1. Überzugsmasse umfassend:
a) ein Polymer mit Anhydrid-Funktionalität, das wenigstens zwei reaktive
Anhydridgruppen enthält und ein durchschnittliches Molekulargewicht von
weniger als 100 000 besitzt,
b) eine Verbindung mit Epoxy- oder Hydroxy-Funktionalität, die wenigstens zwei
Epoxygruppen oder Hydroxygruppen enthält, mit einem durchschnittlichen
Molekulargewicht von weniger als 100 000, worin die Masse 20 bis
80 Gew.-% von Polymer (a) und 80 bis 20 Gew.-% von Verbindung (b)
enthält und
c) einen Katalysator, der eine Vernetzungsreaktion zwischen Verbindung (a) und
Verbindung (b) katalysiert, wobei der genannte Katalysator eine
1,3-Dialkylmidazol-2-thion-Verbindung mit der Struktur
ist, worin R und R&sub1; für C&sub1;-C&sub1;&sub4;-Alkylen (geradkettig oder verzweigt) stehen
und Y und Y&sub1; für H, OH, CO&sub2;H, Aryl, Ether, Amin, Perfluoralkyl, Amid,
Nitril oder Olefin stehen und in einer Menge von 1 bis 10 Gew.-% des
gesamten Bindemittels vorhanden sind.
2. Überzugsmasse nach Anspruch 1, worin Y und Y&sub1; Wasserstoff bedeuten.
3. Überzugsmasse nach Anspruch 1, worin das genannte 1,3-Dialkylimidiazol-2-thion
ausgewählt ist aus der Gruppe, bestehend aus
1-n-Butyl-3-methylimidazol-2-thion,
1-n-Octyl-3-methylimidazol-2-thion,
1-n-Propyl-3-methylimidazol-2-thion, oder
N,N'-Diethylimidazol-2-thion.
4. Überzugsmasse nach einem der Ansprüche 1 bis 3, worin Verbindung (b)
epoxyfunktionell ist und die Überzugsmasse ferner eine säurefunktionelle Verbindung
enthält.
5. Überzugsmasse nach einem der Ansprüche 1 bis 3, worin Verbindung (a) ein
Copolymer darstellt, hergestellt aus einem oder mehreren der Monomeren von
Styrol, Methacrylat oder Acrylaten mit einem oder mehreren der Monomeren von
Itaconsäure, Itaconsäureanhydrid, Maleinsäureanhydrid, Maleinsäure oder
Isobutenylbernsteinsäureanhydrid.
6. Überzugsmasse nach einem der vorgenannten Ansprüche, worin Verbindung (b)
Epoxy-Copolymere darstellt, hergestellt aus Alkylacrylaten oder Alkylmethacrylaten
mit Glycidylacrylaten oder Glycidylmethacrylaten.
7. Überzugsmasse nach Anspruch 6, worin die Epoxy-Copolymere in Kombination mit
den Polyglycidylethern von Sorbit verwendet werden.
8. Überzugsmasse nach Anspruch 1, worin Verbindung (b) ein Copolymer ist, das
Alkylacrylate oder Alkylmethacrylate und hydroxyfunktionelle Acrylate oder
hydroxyfunktionelle Methacrylate enthält.
9. Überzugsmasse nach einem der vorgenannten Ansprüche, worin der
1,3-Dialkylimidazol-2-thion-Katalysator in Verbindung mit Amin-Katalysatoren verwendet wird.
10. Verwendung eines 1,3-Dialkylimidiazol-2-thions der Formel
worin R und R&sub1; für C&sub1;-C&sub1;&sub4;-Alkylen (geradkettig oder verzweigt) stehen und Y und
Y&sub1; für H, OH, CO&sub2;H, Aryl, Ether, Amin, Perfluoralkyl, Amid, Nitril oder Olefin
stehen, als Katalysator zur Katalyse der Vernetzung eines säurefunktionellen
Polymeren und eines anhydridfunktionellen Polymeren mit einer epoxyfunktionellen
Verbindung.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US38989789A | 1989-08-04 | 1989-08-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
DE69016124D1 DE69016124D1 (de) | 1995-03-02 |
DE69016124T2 true DE69016124T2 (de) | 1995-08-10 |
Family
ID=23540200
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69016124T Expired - Fee Related DE69016124T2 (de) | 1989-08-04 | 1990-08-01 | 1,3-Dialkylimidazol-2-thion-Katalysatoren enthaltende Überzugsmischungen. |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP0411927B1 (de) |
JP (1) | JP2911562B2 (de) |
KR (1) | KR0171043B1 (de) |
AT (1) | ATE117348T1 (de) |
AU (1) | AU632353B2 (de) |
CA (1) | CA2022628C (de) |
DE (1) | DE69016124T2 (de) |
ES (1) | ES2066981T3 (de) |
MX (1) | MX174321B (de) |
NZ (1) | NZ234755A (de) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5084542A (en) * | 1990-05-31 | 1992-01-28 | E. I. Du Pont De Nemours And Company | Epoxy/isocyanate crosslinked coatings containing 1,3-disubstituted imidazole-2-thione catalysts |
JPH07503469A (ja) * | 1992-01-24 | 1995-04-13 | レイリー・インダストリーズ・インコーポレーテッド | 新規な硬化剤/促進剤,硬化可能な組成物及びプロセス |
CN1300117C (zh) * | 2005-01-24 | 2007-02-14 | 浙江大学 | 微波辐射合成1,3-二取代咪唑-2-硫酮的方法 |
US11168729B2 (en) * | 2019-03-12 | 2021-11-09 | Earl Allen Size, JR. | Multi-piece anti-vibration locking fastener |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS54124810A (en) * | 1978-03-23 | 1979-09-28 | Nsk Warner Kk | Quenching apparatus |
US4767832A (en) * | 1987-05-29 | 1988-08-30 | Shell Oil Company | Phenolic curing agents for epoxy resins |
ES2043281T3 (es) * | 1989-07-12 | 1993-12-16 | Ici Plc | Dispersante de pigmento. |
-
1990
- 1990-08-01 AT AT90308471T patent/ATE117348T1/de not_active IP Right Cessation
- 1990-08-01 DE DE69016124T patent/DE69016124T2/de not_active Expired - Fee Related
- 1990-08-01 EP EP90308471A patent/EP0411927B1/de not_active Expired - Lifetime
- 1990-08-01 ES ES90308471T patent/ES2066981T3/es not_active Expired - Lifetime
- 1990-08-02 NZ NZ234755A patent/NZ234755A/en unknown
- 1990-08-03 AU AU60108/90A patent/AU632353B2/en not_active Ceased
- 1990-08-03 JP JP2206642A patent/JP2911562B2/ja not_active Expired - Fee Related
- 1990-08-03 MX MX021841A patent/MX174321B/es unknown
- 1990-08-03 CA CA002022628A patent/CA2022628C/en not_active Expired - Lifetime
- 1990-08-03 KR KR1019900012052A patent/KR0171043B1/ko not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
CA2022628A1 (en) | 1991-02-05 |
DE69016124D1 (de) | 1995-03-02 |
AU632353B2 (en) | 1992-12-24 |
MX174321B (es) | 1994-05-06 |
JPH03137118A (ja) | 1991-06-11 |
KR910004765A (ko) | 1991-03-29 |
CA2022628C (en) | 2001-10-02 |
ATE117348T1 (de) | 1995-02-15 |
EP0411927A1 (de) | 1991-02-06 |
NZ234755A (en) | 1991-07-26 |
KR0171043B1 (ko) | 1999-03-30 |
ES2066981T3 (es) | 1995-03-16 |
JP2911562B2 (ja) | 1999-06-23 |
AU6010890A (en) | 1991-02-07 |
EP0411927B1 (de) | 1995-01-18 |
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Owner name: THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ALABAMA |
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8339 | Ceased/non-payment of the annual fee |