CA2308442C - Processes for preparing grafted copolymers - Google Patents
Processes for preparing grafted copolymers Download PDFInfo
- Publication number
- CA2308442C CA2308442C CA002308442A CA2308442A CA2308442C CA 2308442 C CA2308442 C CA 2308442C CA 002308442 A CA002308442 A CA 002308442A CA 2308442 A CA2308442 A CA 2308442A CA 2308442 C CA2308442 C CA 2308442C
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- Canada
- Prior art keywords
- monomer
- polymer
- initiator
- solvent
- parts
- 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
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- 238000000034 method Methods 0.000 title claims abstract description 166
- 229920001577 copolymer Polymers 0.000 title claims abstract description 34
- 230000008569 process Effects 0.000 title description 54
- 239000000178 monomer Substances 0.000 claims abstract description 217
- 239000003999 initiator Substances 0.000 claims abstract description 163
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- 229920000578 graft copolymer Polymers 0.000 claims abstract description 83
- 239000002270 dispersing agent Substances 0.000 claims abstract description 30
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- 239000000376 reactant Substances 0.000 claims abstract description 20
- 239000010687 lubricating oil Substances 0.000 claims abstract description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims description 124
- 239000000203 mixture Substances 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 29
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- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 2
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- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
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- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 claims description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims 2
- 150000001336 alkenes Chemical class 0.000 claims 2
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 2
- BDHGFCVQWMDIQX-UHFFFAOYSA-N 1-ethenyl-2-methylimidazole Chemical compound CC1=NC=CN1C=C BDHGFCVQWMDIQX-UHFFFAOYSA-N 0.000 claims 1
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
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- VQGISNOMGHCEPX-UHFFFAOYSA-N propanenitrile Chemical compound C[CH]C#N VQGISNOMGHCEPX-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000005067 remediation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229920001959 vinylidene polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
- C10M151/02—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- 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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
-
- 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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
- C08F255/04—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms on to ethene-propene copolymers
-
- 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
- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
- C10M143/02—Polyethene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
- C10M143/10—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing aromatic monomer, e.g. styrene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
- C10M145/12—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
- C10M145/16—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate polycarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/022—Ethene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/04—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Graft Or Block Polymers (AREA)
- Lubricants (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6368997P | 1997-10-28 | 1997-10-28 | |
| US60/063,689 | 1997-10-28 | ||
| PCT/GB1998/003208 WO1999021902A1 (en) | 1997-10-28 | 1998-10-28 | Processes for preparing grafted copolymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2308442A1 CA2308442A1 (en) | 1999-05-06 |
| CA2308442C true CA2308442C (en) | 2009-09-01 |
Family
ID=22050841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002308442A Expired - Fee Related CA2308442C (en) | 1997-10-28 | 1998-10-28 | Processes for preparing grafted copolymers |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US6410652B1 (enExample) |
| EP (1) | EP1025138B1 (enExample) |
| JP (1) | JP4377545B2 (enExample) |
| CN (1) | CN1147515C (enExample) |
| AT (1) | ATE290027T1 (enExample) |
| AU (1) | AU757434B2 (enExample) |
| BR (1) | BR9813297A (enExample) |
| CA (1) | CA2308442C (enExample) |
| DE (1) | DE69829197T2 (enExample) |
| WO (1) | WO1999021902A1 (enExample) |
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| BR9813297A (pt) * | 1997-10-28 | 2000-08-29 | Castrol Ltd | Processos de produção de um copolìmero de enxerto, e para produzir um óleo lubrificante, e, produto |
| US20040071980A1 (en) * | 2000-07-12 | 2004-04-15 | Mcbain Douglas S. | Method for in-mold coating a polyolefin article |
| US8058354B2 (en) * | 2001-02-09 | 2011-11-15 | Eastman Chemical Company | Modified carboxylated polyolefins and their use as adhesion promoters |
| US6548606B1 (en) | 2002-01-23 | 2003-04-15 | Infineum International Ltd. | Method of forming grafted copolymers |
| WO2003099890A2 (en) * | 2002-05-24 | 2003-12-04 | Castrol Limited | Preparation of monomers for grafting to polyolefins, and lubricating oil compositions containing grafted copolymer |
| US7163913B2 (en) | 2003-07-01 | 2007-01-16 | Infineum International Limited | Viscosity index improvers for lubricating oil compositions |
| US7514393B2 (en) * | 2003-11-21 | 2009-04-07 | Castrol Limited | Preparation of functional monomers for grafting to low molecular weight polyalkenes and their use in the preparation of dispersants and lubricating oil compositions containing dispersant polyalkenes |
| DE102004005172A1 (de) * | 2004-02-02 | 2005-08-18 | Aventis Pharma Deutschland Gmbh | Indazolderivate als Inhibitoren der Hormon Sensitiven Lipase |
| ITMI20040751A1 (it) * | 2004-04-16 | 2004-07-16 | Polimeri Europa Spa | Procedimento per modificare le proprieta' reologiche di polimeri ep d m e miscele di ep d m con poli-alfaolefine |
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| CN115991032B (zh) * | 2021-10-20 | 2024-08-20 | 中国石油化工股份有限公司 | 一种聚丙烯复合薄膜及其制备方法和应用 |
| CN115991021B (zh) * | 2021-10-20 | 2024-09-17 | 中国石油化工股份有限公司 | 一种聚丙烯复合薄膜及其制备方法和应用 |
| WO2025125893A1 (en) | 2023-12-14 | 2025-06-19 | Infineum International Limited | Lubricant compositions for reduced pre-ignition in hydrogen fueled engines |
| WO2025126133A1 (en) | 2023-12-14 | 2025-06-19 | Infineum International Limited | Lubricant compositions containing phosphorus for use in hydrogen fueled engines |
| WO2025126134A1 (en) | 2023-12-14 | 2025-06-19 | Infineum International Limited | Lubricant compositions containing detergent for reduced abnormal combustion events in hydrogen fueled engines |
| WO2025125894A1 (en) | 2023-12-14 | 2025-06-19 | Infineum International Limited | Lubricant compositions containing magnesium detergent for reduced pre-ignition in hydrogen fueled engines |
| WO2025125892A1 (en) | 2023-12-14 | 2025-06-19 | Infineum International Limited | Lubricant compositions containing molybdenum for reduced pre-ignition in hydrogen fueled engines |
| WO2025126063A1 (en) | 2023-12-14 | 2025-06-19 | Infineum International Limited | Lubricant compositions containing silicon for reduced pre-ignition in hydrogen fueled engines |
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| US3593011A (en) | 1968-05-09 | 1971-07-13 | Exxon Research Engineering Co | Analogue control device for chemical processes |
| US3608001A (en) | 1969-08-26 | 1971-09-21 | Exxon Research Engineering Co | Controlled degradation of polypropylene in extruder-reactor |
| US3563972A (en) | 1969-10-15 | 1971-02-16 | Exxon Research Engineering Co | Low melt elasticity composition of polypropylene |
| US4508592A (en) | 1976-08-04 | 1985-04-02 | Exxon Research & Engineering Co. | Elastomer extrusion drying with gas injection |
| US4384072A (en) | 1981-09-30 | 1983-05-17 | Exxon Research & Engineering Co. | Process for the manufacture of halogenated elastomers |
| US4483886A (en) | 1982-05-27 | 1984-11-20 | Exxon Research & Engineering Co. | Method for making free-flowing, melt-coated rubber pellets |
| US4548995A (en) | 1983-04-01 | 1985-10-22 | Exxon Research & Engineering Co. | Process for the manufacture of halogenated polymers |
| US4501859A (en) | 1983-04-01 | 1985-02-26 | Exxon Research & Engineering Co. | Process for the manufacture of halogenated polymers |
| US4554326A (en) | 1983-04-01 | 1985-11-19 | Exxon Research & Engineering Co. | Process for the manufacture of halogenated polymers |
| US4513116A (en) | 1983-04-01 | 1985-04-23 | Exxon Research And Engineering Co. | Process for the manufacture of halogenated polymers |
| US4632963A (en) | 1984-04-05 | 1986-12-30 | Exxon Research & Engineering Co. | Halogenated butyl rubber |
| US4703091A (en) | 1984-04-05 | 1987-10-27 | Exxon Research & Engineering Co. | Halogenated butyl rubber |
| US4563506A (en) | 1984-09-17 | 1986-01-07 | Exxon Research & Engineering Co. | Extrusion process for preparing improved brominated butyl rubber |
| US5087674A (en) | 1984-10-01 | 1992-02-11 | Exxon Research & Engineering | Acid scavenged polymer halogenation |
| US4957974A (en) * | 1988-03-29 | 1990-09-18 | Rohm And Haas Company | Graft copolymers and blends thereof with polyolefins |
| US5298565A (en) * | 1989-04-05 | 1994-03-29 | The Lubrizol Corporation | Graft copolymers and lubricants containing such as dispersant-viscosity improvers |
| US5298555A (en) * | 1990-01-09 | 1994-03-29 | American Cyanamid Company | Low settling water-in-oil emulsions |
| CA2036862A1 (en) | 1990-02-23 | 1991-08-24 | Tony L. Caines | Continuous process for producing adducted epm or epdm oil solution |
| US5070624A (en) | 1990-04-20 | 1991-12-10 | Exxon Chemical Patents Inc. | Two-stage pneumatic conveying process for rubber cooling |
| US5424367A (en) * | 1991-12-13 | 1995-06-13 | Exxon Chemical Patents Inc. | Multiple reaction process in melt processing equipment |
| US5663126A (en) | 1994-10-21 | 1997-09-02 | Castrol Limited | Polar grafted polyolefins, methods for their manufacture, and lubricating oil compositions containing them |
| US5523008A (en) * | 1994-10-21 | 1996-06-04 | Castrol Limited | Polar grafted polyolefins, methods for their manufacture, and lubricating oil compositions containing them |
| BR9813297A (pt) * | 1997-10-28 | 2000-08-29 | Castrol Ltd | Processos de produção de um copolìmero de enxerto, e para produzir um óleo lubrificante, e, produto |
-
1998
- 1998-10-28 BR BR9813297-0A patent/BR9813297A/pt not_active IP Right Cessation
- 1998-10-28 WO PCT/GB1998/003208 patent/WO1999021902A1/en not_active Ceased
- 1998-10-28 AU AU97526/98A patent/AU757434B2/en not_active Ceased
- 1998-10-28 DE DE69829197T patent/DE69829197T2/de not_active Expired - Lifetime
- 1998-10-28 AT AT98951565T patent/ATE290027T1/de not_active IP Right Cessation
- 1998-10-28 CA CA002308442A patent/CA2308442C/en not_active Expired - Fee Related
- 1998-10-28 EP EP98951565A patent/EP1025138B1/en not_active Expired - Lifetime
- 1998-10-28 JP JP2000518007A patent/JP4377545B2/ja not_active Expired - Fee Related
- 1998-10-28 CN CNB988107848A patent/CN1147515C/zh not_active Expired - Fee Related
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2000
- 2000-04-06 US US09/529,013 patent/US6410652B1/en not_active Expired - Lifetime
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2002
- 2002-03-11 US US10/093,517 patent/US6723796B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE290027T1 (de) | 2005-03-15 |
| DE69829197D1 (de) | 2005-04-07 |
| AU9752698A (en) | 1999-05-17 |
| US6723796B2 (en) | 2004-04-20 |
| EP1025138A1 (en) | 2000-08-09 |
| WO1999021902A1 (en) | 1999-05-06 |
| JP4377545B2 (ja) | 2009-12-02 |
| JP2001521049A (ja) | 2001-11-06 |
| CN1278274A (zh) | 2000-12-27 |
| US20020183456A1 (en) | 2002-12-05 |
| US6410652B1 (en) | 2002-06-25 |
| CA2308442A1 (en) | 1999-05-06 |
| BR9813297A (pt) | 2000-08-29 |
| EP1025138B1 (en) | 2005-03-02 |
| CN1147515C (zh) | 2004-04-28 |
| AU757434B2 (en) | 2003-02-20 |
| DE69829197T2 (de) | 2006-02-16 |
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| MKLA | Lapsed |
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