CA2971185C - Oxidized alpha-olefins in rust preventive coatings - Google Patents
Oxidized alpha-olefins in rust preventive coatings Download PDFInfo
- Publication number
- CA2971185C CA2971185C CA2971185A CA2971185A CA2971185C CA 2971185 C CA2971185 C CA 2971185C CA 2971185 A CA2971185 A CA 2971185A CA 2971185 A CA2971185 A CA 2971185A CA 2971185 C CA2971185 C CA 2971185C
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- CA
- Canada
- Prior art keywords
- coating composition
- oxidized
- olefin
- carbon atoms
- acid
- 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.)
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 title abstract description 18
- 238000000576 coating method Methods 0.000 title description 25
- 239000004711 α-olefin Substances 0.000 title description 10
- 230000003449 preventive effect Effects 0.000 title description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 64
- 239000003085 diluting agent Substances 0.000 claims abstract description 61
- 239000002253 acid Substances 0.000 claims abstract description 59
- 239000008199 coating composition Substances 0.000 claims abstract description 59
- 150000002148 esters Chemical class 0.000 claims abstract description 50
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 229920000642 polymer Polymers 0.000 claims abstract description 41
- 229910052751 metal Inorganic materials 0.000 claims abstract description 17
- 239000002184 metal Substances 0.000 claims abstract description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims description 61
- 229930195733 hydrocarbon Natural products 0.000 claims description 33
- 150000002430 hydrocarbons Chemical class 0.000 claims description 33
- 239000004215 Carbon black (E152) Substances 0.000 claims description 32
- 239000001993 wax Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 229920001577 copolymer Polymers 0.000 claims description 15
- 238000005886 esterification reaction Methods 0.000 claims description 13
- 230000032050 esterification Effects 0.000 claims description 12
- 238000005260 corrosion Methods 0.000 claims description 9
- 230000007797 corrosion Effects 0.000 claims description 9
- 150000001336 alkenes Chemical class 0.000 claims description 8
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 7
- 239000012169 petroleum derived wax Substances 0.000 claims description 7
- 235000019381 petroleum wax Nutrition 0.000 claims description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 6
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- 229920000147 Styrene maleic anhydride Polymers 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 47
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- 239000000306 component Substances 0.000 description 28
- 239000000463 material Substances 0.000 description 26
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- 239000011575 calcium Substances 0.000 description 18
- -1 alkaline earth metal sulfonate Chemical class 0.000 description 17
- 238000005516 engineering process Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 11
- 125000001183 hydrocarbyl group Chemical group 0.000 description 11
- 239000007921 spray Substances 0.000 description 11
- 239000002480 mineral oil Substances 0.000 description 10
- 235000010446 mineral oil Nutrition 0.000 description 10
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
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- 239000012141 concentrate Substances 0.000 description 9
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
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- 241000894007 species Species 0.000 description 6
- 239000001530 fumaric acid Substances 0.000 description 5
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- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
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- 239000000047 product Substances 0.000 description 5
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 5
- 229940044603 styrene Drugs 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical class C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 159000000007 calcium salts Chemical class 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- 239000002199 base oil Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 229940063557 methacrylate Drugs 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000002952 polymeric resin Substances 0.000 description 3
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 235000001508 sulfur Nutrition 0.000 description 3
- 229960005349 sulfur Drugs 0.000 description 3
- 229920002554 vinyl polymer Polymers 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
- XMVBHZBLHNOQON-UHFFFAOYSA-N 2-butyl-1-octanol Chemical compound CCCCCCC(CO)CCCC XMVBHZBLHNOQON-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- C09D5/08—Anti-corrosive paints
- C09D5/082—Anti-corrosive paints characterised by the anti-corrosive pigment
- C09D5/086—Organic or non-macromolecular compounds
-
- 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
- C09D5/08—Anti-corrosive paints
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/14—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to metal, e.g. car bodies
-
- 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- 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
- C08K5/01—Hydrocarbons
-
- 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
-
- 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
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Paints Or Removers (AREA)
- Lubricants (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Applications Claiming Priority (3)
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| US201462091692P | 2014-12-15 | 2014-12-15 | |
| US62/091,692 | 2014-12-15 | ||
| PCT/US2015/065551 WO2016100206A1 (en) | 2014-12-15 | 2015-12-14 | Oxidized alpha-olefins in rust preventive coatings |
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| CA2971185A1 CA2971185A1 (en) | 2016-06-23 |
| CA2971185C true CA2971185C (en) | 2023-07-18 |
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|---|---|---|---|
| CA2971185A Active CA2971185C (en) | 2014-12-15 | 2015-12-14 | Oxidized alpha-olefins in rust preventive coatings |
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|---|---|
| US (1) | US10144835B2 (enExample) |
| EP (1) | EP3234028B1 (enExample) |
| JP (1) | JP6637046B2 (enExample) |
| KR (1) | KR102548670B1 (enExample) |
| CN (1) | CN107207883B (enExample) |
| CA (1) | CA2971185C (enExample) |
| WO (1) | WO2016100206A1 (enExample) |
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| CA2917677A1 (en) * | 2015-12-09 | 2017-06-09 | Interstate Corrpack Llc | Recyclable leak resistant corrugated box |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2501731A (en) | 1946-10-14 | 1950-03-28 | Union Oil Co | Modified lubricating oil |
| US2616911A (en) | 1951-03-16 | 1952-11-04 | Lubrizol Corp | Organic alkaline earth metal complexes formed by use of sulfonic promoters |
| US2616925A (en) | 1951-03-16 | 1952-11-04 | Lubrizol Corp | Organic alkaline earth metal complexes formed by use of thiophosphoric promoters |
| US2616905A (en) | 1952-03-13 | 1952-11-04 | Lubrizol Corp | Organic alkaline earth metal complexes and methods of making same |
| US2777874A (en) | 1952-11-03 | 1957-01-15 | Lubrizol Corp | Metal complexes and methods of making same |
| US2808423A (en) | 1953-09-03 | 1957-10-01 | Sun Oil Co | Catalytic partial oxidation of hydrocarbons |
| US3488284A (en) | 1959-12-10 | 1970-01-06 | Lubrizol Corp | Organic metal compositions and methods of preparing same |
| US3282835A (en) | 1963-02-12 | 1966-11-01 | Lubrizol Corp | Carbonated bright stock sulfonates and lubricants containing them |
| US3250715A (en) | 1964-02-04 | 1966-05-10 | Lubrizol Corp | Terpolymer product and lubricating composition containing it |
| US3320162A (en) | 1964-05-22 | 1967-05-16 | Phillips Petroleum Co | Increasing the base number of calcium petroleum sulfonate |
| US3318809A (en) | 1965-07-13 | 1967-05-09 | Bray Oil Co | Counter current carbonation process |
| US3365396A (en) | 1965-12-28 | 1968-01-23 | Texaco Inc | Overbased calcium sulfonate |
| US3384585A (en) | 1966-08-29 | 1968-05-21 | Phillips Petroleum Co | Overbasing lube oil additives |
| US3565843A (en) | 1967-12-20 | 1971-02-23 | Rudolph Kassinger | Organic rust inhibiting composition |
| US3629109A (en) | 1968-12-19 | 1971-12-21 | Lubrizol Corp | Basic magnesium salts processes and lubricants and fuels containing the same |
| US4426229A (en) | 1976-11-26 | 1984-01-17 | Petrolite Corporation | Oxidized alpha-olefins |
| US6017370A (en) | 1998-09-25 | 2000-01-25 | The Lubrizol Corporation | Fumarate copolymers and acylated alkanolamines as low temperature flow improvers |
| CN1222586C (zh) | 1998-10-14 | 2005-10-12 | 杰富意钢铁株式会社 | 涂料组合物及润滑处理金属板 |
| US6312509B1 (en) | 2000-08-10 | 2001-11-06 | Ebrahim Moradian | Rust preventive coating composition |
| US7709425B2 (en) | 2005-10-27 | 2010-05-04 | Chevron Phillips Chemical Company Lp | Oxidized olefin wax pour point depressants |
| US20100197536A1 (en) | 2007-05-24 | 2010-08-05 | Mosier Patrick E | Lubricating Composition Containing Ashfree Antiwear Agent Based on Hydroxypolycarboxylic Acid Derivative and a Molybdenum Compound |
| US8268338B2 (en) | 2007-07-09 | 2012-09-18 | Eastern Michigan University | Bactericidal silver surfactant delivery into coating and polymer compositions |
| CN104277144A (zh) * | 2008-07-31 | 2015-01-14 | 卢布里佐尔公司 | 共聚物及其润滑组合物 |
| JP2013540203A (ja) | 2010-10-05 | 2013-10-31 | ビーエーエスエフ ソシエタス・ヨーロピア | 界面活性剤を含有する水性組成物で金属表面を不動態化する方法 |
| US9127237B2 (en) | 2011-06-28 | 2015-09-08 | Sasol Germany Gmbh | Surfactant compositions |
| US9757603B2 (en) | 2011-08-11 | 2017-09-12 | Cbi Polymers, Inc. | Polymer composition |
| US20130068134A1 (en) | 2011-09-16 | 2013-03-21 | Chevron Phillips Chemical Company Lp | Oxidized Alpha Olefins |
| JP6242349B2 (ja) | 2012-03-08 | 2017-12-06 | ザ ルブリゾル コーポレイションＴｈｅ Ｌｕｂｒｉｚｏｌ Ｃｏｒｐｏｒａｔｉｏｎ | 改良された腐食保護を提供する、水性コーティング、組成物およびその方法 |
| JP6367336B2 (ja) | 2013-12-19 | 2018-08-01 | ザ ルブリゾル コーポレイションＴｈｅ Ｌｕｂｒｉｚｏｌ Ｃｏｒｐｏｒａｔｉｏｎ | 防錆コーティング中の硬化天然油 |
-
2015
- 2015-12-14 KR KR1020177017226A patent/KR102548670B1/ko active Active
- 2015-12-14 US US15/536,304 patent/US10144835B2/en active Active
- 2015-12-14 CA CA2971185A patent/CA2971185C/en active Active
- 2015-12-14 EP EP15823057.3A patent/EP3234028B1/en active Active
- 2015-12-14 WO PCT/US2015/065551 patent/WO2016100206A1/en not_active Ceased
- 2015-12-14 CN CN201580076071.2A patent/CN107207883B/zh active Active
- 2015-12-14 JP JP2017531670A patent/JP6637046B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20170362444A1 (en) | 2017-12-21 |
| EP3234028A1 (en) | 2017-10-25 |
| EP3234028B1 (en) | 2021-10-13 |
| WO2016100206A1 (en) | 2016-06-23 |
| JP6637046B2 (ja) | 2020-01-29 |
| KR20170094244A (ko) | 2017-08-17 |
| CN107207883B (zh) | 2019-10-25 |
| KR102548670B1 (ko) | 2023-06-27 |
| JP2018505924A (ja) | 2018-03-01 |
| US10144835B2 (en) | 2018-12-04 |
| CA2971185A1 (en) | 2016-06-23 |
| CN107207883A (zh) | 2017-09-26 |
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