CA2048241A1 - Polymeric adhesive and anti-corrosion agents - Google Patents
Polymeric adhesive and anti-corrosion agentsInfo
- Publication number
- CA2048241A1 CA2048241A1 CA002048241A CA2048241A CA2048241A1 CA 2048241 A1 CA2048241 A1 CA 2048241A1 CA 002048241 A CA002048241 A CA 002048241A CA 2048241 A CA2048241 A CA 2048241A CA 2048241 A1 CA2048241 A1 CA 2048241A1
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- vinylimidazole
- composition
- vinylpyridine
- vinylpyrrolidone
- 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.)
- Abandoned
Links
- 238000005260 corrosion Methods 0.000 title claims abstract description 19
- 239000003795 chemical substances by application Substances 0.000 title abstract description 11
- 239000000853 adhesive Substances 0.000 title abstract description 8
- 230000001070 adhesive effect Effects 0.000 title description 6
- 229920000642 polymer Polymers 0.000 claims abstract description 117
- 239000000203 mixture Substances 0.000 claims abstract description 53
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 49
- 229910052751 metal Inorganic materials 0.000 claims abstract description 31
- 239000002184 metal Substances 0.000 claims abstract description 31
- 238000000576 coating method Methods 0.000 claims abstract description 8
- 239000011248 coating agent Substances 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 51
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 40
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 38
- 229910052802 copper Inorganic materials 0.000 claims description 35
- 239000010949 copper Substances 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- -1 poly(arylene sulfide Chemical compound 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 21
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 11
- 230000007797 corrosion Effects 0.000 claims description 8
- 150000002739 metals Chemical class 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- OZFIGURLAJSLIR-UHFFFAOYSA-N 1-ethenyl-2h-pyridine Chemical compound C=CN1CC=CC=C1 OZFIGURLAJSLIR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 2
- 229920001169 thermoplastic Polymers 0.000 claims 5
- 239000004416 thermosoftening plastic Substances 0.000 claims 5
- GECBFCPDQHIKOX-UHFFFAOYSA-N 1-ethenylimidazole;1-ethenylpyrrolidin-2-one Chemical group C=CN1C=CN=C1.C=CN1CCCC1=O GECBFCPDQHIKOX-UHFFFAOYSA-N 0.000 claims 2
- POCJYFGFHPRKEQ-UHFFFAOYSA-N 1-ethenylimidazole;4-ethenylpyridine Chemical compound C=CN1C=CN=C1.C=CC1=CC=NC=C1 POCJYFGFHPRKEQ-UHFFFAOYSA-N 0.000 claims 1
- FSMWEJZXDWRBEN-UHFFFAOYSA-N 4-ethenylpyridine;1-ethenylpyrrolidin-2-one Chemical group C=CN1CCCC1=O.C=CC1=CC=NC=C1 FSMWEJZXDWRBEN-UHFFFAOYSA-N 0.000 claims 1
- 229910000881 Cu alloy Inorganic materials 0.000 claims 1
- 229920000412 polyarylene Polymers 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- 239000007769 metal material Substances 0.000 abstract 2
- XNCGVYCIJPKGKW-UHFFFAOYSA-N 1h-imidazole;pyrrolidin-2-one Chemical compound C1=CNC=N1.O=C1CCCN1 XNCGVYCIJPKGKW-UHFFFAOYSA-N 0.000 abstract 1
- VXUYSKXBQCGVSG-UHFFFAOYSA-N pyridine;pyrrolidin-2-one Chemical compound C1=CC=NC=C1.O=C1CCCN1 VXUYSKXBQCGVSG-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000004734 Polyphenylene sulfide Substances 0.000 description 32
- 239000000243 solution Substances 0.000 description 23
- 229920001577 copolymer Polymers 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 239000000178 monomer Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229920001519 homopolymer Polymers 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 7
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 6
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 239000012964 benzotriazole Substances 0.000 description 5
- 230000005587 bubbling Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 238000000465 moulding Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000007586 pull-out test Methods 0.000 description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
- UFHSKEHEWFGEFH-UHFFFAOYSA-N (2,5-dioxopyrrolidin-3-yl) prop-2-enoate Chemical compound C=CC(=O)OC1CC(=O)NC1=O UFHSKEHEWFGEFH-UHFFFAOYSA-N 0.000 description 1
- NAGSMIOYEJTYQT-UHFFFAOYSA-N 1-ethenyl-3,3,5-trimethylpyrrolidin-2-one Chemical compound CC1CC(C)(C)C(=O)N1C=C NAGSMIOYEJTYQT-UHFFFAOYSA-N 0.000 description 1
- HQGPZXPTJWUDQR-UHFFFAOYSA-N 1-ethenyl-5-methylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1C=C HQGPZXPTJWUDQR-UHFFFAOYSA-N 0.000 description 1
- MLMGJTAJUDSUKA-UHFFFAOYSA-N 2-ethenyl-1h-imidazole Chemical compound C=CC1=NC=CN1 MLMGJTAJUDSUKA-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- BJPRMONRDLJVCD-UHFFFAOYSA-N 3-benzyl-1-ethenylpyrrolidin-2-one Chemical compound O=C1N(C=C)CCC1CC1=CC=CC=C1 BJPRMONRDLJVCD-UHFFFAOYSA-N 0.000 description 1
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 description 1
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 101100490446 Penicillium chrysogenum PCBAB gene Proteins 0.000 description 1
- 101000900567 Pisum sativum Disease resistance response protein Pi49 Proteins 0.000 description 1
- 239000004693 Polybenzimidazole Substances 0.000 description 1
- 101100514056 Rhodobacter capsulatus modD gene Proteins 0.000 description 1
- 229920013632 Ryton Polymers 0.000 description 1
- 239000004736 Ryton® Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 241001080526 Vertica Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002991 molded plastic Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000075 poly(4-vinylpyridine) Polymers 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000001175 rotational moulding Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/301—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen or carbon in the main chain of the macromolecule, not provided for in group H01B3/302
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/02—Polythioethers; Polythioether-ethers
-
- 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
- C09J181/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Adhesives based on polysulfones; Adhesives based on derivatives of such polymers
- C09J181/02—Polythioethers; Polythioether-ethers
-
- 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
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of 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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
- Laminated Bodies (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/568,109 | 1990-08-16 | ||
| US07/568,109 US5239002A (en) | 1990-08-16 | 1990-08-16 | Polymeric adhesive and anti-corrosion agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2048241A1 true CA2048241A1 (en) | 1992-02-17 |
Family
ID=24269950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002048241A Abandoned CA2048241A1 (en) | 1990-08-16 | 1991-07-31 | Polymeric adhesive and anti-corrosion agents |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5239002A (enExample) |
| EP (1) | EP0471336A3 (enExample) |
| JP (1) | JPH04272193A (enExample) |
| KR (1) | KR920004525A (enExample) |
| CA (1) | CA2048241A1 (enExample) |
| TW (1) | TW228006B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5480950A (en) * | 1992-09-28 | 1996-01-02 | Kabi Pharmacia Ophthalmics, Inc. | High refractive index hydrogels and uses thereof |
| US5522842A (en) * | 1994-03-11 | 1996-06-04 | Poly-Med, Inc. | Absorbable Ε-caprolactone polymers as suture coatings displaying auto catalyzed hydrolysis |
| US8226683B2 (en) * | 1994-03-11 | 2012-07-24 | Poly-Med, Inc. | High strength nitrogenous caprolactone copolymers and biomedical constructs therefrom |
| US5853621A (en) * | 1995-05-26 | 1998-12-29 | Monsanto Company | Corrosion resistant paint |
| US5723231A (en) * | 1996-12-09 | 1998-03-03 | Motorola, Inc. | Polymer electrolyte and an electrochemical cell containing the electrolyte |
| US5882799A (en) * | 1996-12-16 | 1999-03-16 | Vernay Laboratories, Inc. | Polymeric coupling agents for the adhesion of macromolecular materials and metal substrates |
| DE10131723A1 (de) * | 2001-06-30 | 2003-01-16 | Henkel Kgaa | Korrosionsschutzmittel und Korrosionsschutzverfahren für Metalloberflächen |
| DE10310972A1 (de) * | 2003-03-13 | 2004-09-23 | Basf Ag | Stickstoffhaltige Polymere für die Metalloberflächenbehandlung |
| KR100972451B1 (ko) * | 2008-01-02 | 2010-07-26 | 주식회사 효성 | 라벨 공급기 |
| US20110079589A1 (en) * | 2008-06-06 | 2011-04-07 | Nv Bekaert Sa | Electrically conductive yarn with reduced torsions |
| EP2329069B1 (en) * | 2008-07-22 | 2011-11-30 | NV Bekaert SA | Yarn for car seat heating with suitable lubricant |
| CN105505289B (zh) * | 2015-12-27 | 2018-01-19 | 上海创益中空玻璃材料有限公司 | 高强度聚硫防水结构胶及其制备方法 |
| JPWO2018131495A1 (ja) * | 2017-01-10 | 2019-11-07 | Ｊｓｒ株式会社 | カバー膜形成方法、基材の処理方法及び組成物 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE756724A (fr) * | 1969-09-29 | 1971-03-29 | Phillips Petroleum Co | Stratifies cuivre-sulfure de polyarylene et procede de preparation |
| US3894983A (en) * | 1973-06-13 | 1975-07-15 | Phillips Petroleum Co | Poly(arylene sulfide) coating |
| JPS5133132A (en) * | 1974-09-14 | 1976-03-22 | Honey Kasei Kk | Kinzoku gomu no setsuchakuhoho |
| JPS5133133A (en) * | 1974-09-14 | 1976-03-22 | Honey Kasei Kk | Kinzoku gomu no setsuchakuhoho |
| US4017450A (en) * | 1976-03-29 | 1977-04-12 | Phillips Petroleum Company | Inhibition of poly(arylene sulfide) resin induced metal corrosion |
| US4115344A (en) * | 1977-07-05 | 1978-09-19 | Phillips Petroleum Company | Mold corrosion inhibition in poly(arylene) sulfide processing |
| JPS55500110A (enExample) * | 1978-03-06 | 1980-02-28 | ||
| DE3209224A1 (de) * | 1982-03-13 | 1983-09-15 | Basf Ag | Verfahren zur herstellung von unloeslichen, nur wenig quellbaren polymerisaten von basischen vinylheterocyclen und deren verwendung |
| US4748169A (en) * | 1985-01-16 | 1988-05-31 | Dainippon Ink And Chemicals, Inc. | Polyarylene sulfide resin composition |
| JPS61200166A (ja) * | 1985-02-28 | 1986-09-04 | Dainippon Ink & Chem Inc | ポリアリ−レンスルフイド樹脂組成物 |
| JPS62109850A (ja) * | 1985-11-08 | 1987-05-21 | Kureha Chem Ind Co Ltd | ポリアリ−レンチオエ−テルの溶融成形機器の腐蝕防止法 |
| JPS62252448A (ja) * | 1986-04-24 | 1987-11-04 | Sumitomo Bakelite Co Ltd | 樹脂組成物 |
| US4833022A (en) * | 1987-08-20 | 1989-05-23 | Olin Corporation | Polymer/copper laminate and method for fabrication thereof |
| US4916179A (en) * | 1988-06-02 | 1990-04-10 | Phillips Petroleum Company | Inhibition of poly(arylene sulfide) resin induced metal corrosion |
-
1990
- 1990-08-16 US US07/568,109 patent/US5239002A/en not_active Expired - Fee Related
-
1991
- 1991-07-31 CA CA002048241A patent/CA2048241A1/en not_active Abandoned
- 1991-08-13 EP EP19910113569 patent/EP0471336A3/en not_active Withdrawn
- 1991-08-14 KR KR1019910014075A patent/KR920004525A/ko not_active Ceased
- 1991-08-16 JP JP3205785A patent/JPH04272193A/ja active Pending
- 1991-08-21 TW TW080106631A patent/TW228006B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| KR920004525A (ko) | 1992-03-27 |
| EP0471336A2 (en) | 1992-02-19 |
| JPH04272193A (ja) | 1992-09-28 |
| US5239002A (en) | 1993-08-24 |
| TW228006B (enExample) | 1994-08-11 |
| EP0471336A3 (en) | 1993-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 19940201 |