JP4234325B2 - 油組成物用星形ポリマー粘度指数向上剤 - Google Patents
油組成物用星形ポリマー粘度指数向上剤 Download PDFInfo
- Publication number
- JP4234325B2 JP4234325B2 JP2000532489A JP2000532489A JP4234325B2 JP 4234325 B2 JP4234325 B2 JP 4234325B2 JP 2000532489 A JP2000532489 A JP 2000532489A JP 2000532489 A JP2000532489 A JP 2000532489A JP 4234325 B2 JP4234325 B2 JP 4234325B2
- Authority
- JP
- Japan
- Prior art keywords
- block
- star polymer
- molecular weight
- star
- viscosity
- 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 - Lifetime
Links
- 229920000642 polymer Polymers 0.000 title claims description 108
- 239000000203 mixture Substances 0.000 title claims description 15
- 239000003921 oil Substances 0.000 claims description 32
- 238000005984 hydrogenation reaction Methods 0.000 claims description 22
- 239000005062 Polybutadiene Substances 0.000 claims description 20
- 229920002857 polybutadiene Polymers 0.000 claims description 20
- 229920001195 polyisoprene Polymers 0.000 claims description 18
- 239000004793 Polystyrene Substances 0.000 claims description 15
- 229920002223 polystyrene Polymers 0.000 claims description 15
- 239000002199 base oil Substances 0.000 claims description 13
- 229920001400 block copolymer Polymers 0.000 claims description 11
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical group C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 8
- 239000007822 coupling agent Substances 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 239000012141 concentrate Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 21
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical class CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 19
- 230000000994 depressogenic effect Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 239000010687 lubricating oil Substances 0.000 description 8
- 238000005086 pumping Methods 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000010705 motor oil Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 238000005259 measurement Methods 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- PERLSLNQWLZSLS-UHFFFAOYSA-N ethyl hexanoate;nickel Chemical compound [Ni].CCCCCC(=O)OCC PERLSLNQWLZSLS-UHFFFAOYSA-N 0.000 description 2
- 239000003879 lubricant additive Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- 238000011925 1,2-addition Methods 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000010718 automatic transmission oil Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003599 detergent Substances 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
- 238000013213 extrapolation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229920003046 tetrablock copolymer Polymers 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 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
- C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
- C10M143/12—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing conjugated diene
-
- 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
- C08F297/044—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes using a coupling agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
- C08L53/025—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes modified
-
- 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
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/06—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/251—Alcohol-fuelled engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/28—Rotary engines
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Lubricants (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7523098P | 1998-02-19 | 1998-02-19 | |
| US60/075,230 | 1998-02-19 | ||
| PCT/EP1999/001003 WO1999042542A1 (en) | 1998-02-19 | 1999-02-16 | Star polymer viscosity index improver for oil compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002504589A JP2002504589A (ja) | 2002-02-12 |
| JP2002504589A5 JP2002504589A5 (enExample) | 2006-03-09 |
| JP4234325B2 true JP4234325B2 (ja) | 2009-03-04 |
Family
ID=22124385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000532489A Expired - Lifetime JP4234325B2 (ja) | 1998-02-19 | 1999-02-16 | 油組成物用星形ポリマー粘度指数向上剤 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6034042A (enExample) |
| EP (1) | EP1064347B1 (enExample) |
| JP (1) | JP4234325B2 (enExample) |
| KR (1) | KR100549457B1 (enExample) |
| CN (1) | CN1114683C (enExample) |
| AU (1) | AU738659B2 (enExample) |
| BR (1) | BR9908068B1 (enExample) |
| CA (1) | CA2321006C (enExample) |
| DE (1) | DE69909265T2 (enExample) |
| ES (1) | ES2201684T3 (enExample) |
| RU (1) | RU2201939C2 (enExample) |
| TW (1) | TW428025B (enExample) |
| WO (1) | WO1999042542A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8716215B2 (en) * | 2005-01-13 | 2014-05-06 | Regenerx Biopharmaceuticals, Inc. | Method of treating or preventing tissue deterioration, injury or damage due to a neuro-, muscular- or neuro-muscular-degenerative disease, or restore tissue adversely affected by said disease |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7034079B2 (en) * | 1999-10-20 | 2006-04-25 | The Lubrizol Corporation | Radial polymers prepared by stabilized free radical polymerization |
| US20030083209A1 (en) * | 2001-10-22 | 2003-05-01 | Moodycliffe Timothy I. | Viscosity modification of petroleum distillates |
| JP3932424B2 (ja) * | 2002-03-07 | 2007-06-20 | ジャパン パシフィック エンタープライズ株式会社 | 潤滑油混合用組成物 |
| US7018962B2 (en) * | 2003-06-12 | 2006-03-28 | Infineum International Limited | Viscosity index improver concentrates |
| US7163913B2 (en) * | 2003-07-01 | 2007-01-16 | Infineum International Limited | Viscosity index improvers for lubricating oil compositions |
| EP1725637A4 (en) * | 2003-11-26 | 2010-07-28 | Arkema Inc | THICKENERS BASED ON CONTROLLED RADICAL ACRYLIC COPOLYMERS |
| US20070105731A1 (en) * | 2005-11-04 | 2007-05-10 | Chin Chu | Lubricating oil compositions |
| RU2439130C2 (ru) | 2006-03-10 | 2012-01-10 | КРЭЙТОН ПОЛИМЕРС Ю.Эс. ЭлЭлСи | Добавка, улучшающая индекс вязкости, для смазочных масел |
| WO2008018445A1 (en) * | 2006-08-08 | 2008-02-14 | Asahi Kasei Chemicals Corporation | Hydrogenated block copolymers and crosslinking compositions conatining the same |
| US8785546B2 (en) | 2008-08-29 | 2014-07-22 | Kuraray Co., Ltd. | Hydrogenated block copolymer and composition containing same |
| CN101899135A (zh) * | 2010-02-10 | 2010-12-01 | 大连理工大学 | 星形高抗冲聚苯乙烯及其制备方法 |
| EP2363454B1 (en) * | 2010-02-23 | 2018-09-26 | Infineum International Limited | Use of a lubricating oil composition |
| US8999905B2 (en) * | 2010-10-25 | 2015-04-07 | Afton Chemical Corporation | Lubricant additive |
| US9133413B2 (en) * | 2011-12-21 | 2015-09-15 | Infineum International Limited | Viscosity index improvers for lubricating oil compositions |
| CN103665281B (zh) * | 2012-08-31 | 2016-04-13 | 中国石油化工股份有限公司 | 一种四臂辐射星形无规共聚物及其制备方法 |
| CN103834457B (zh) * | 2012-11-23 | 2016-04-06 | 中国石油天然气股份有限公司 | 一种抑制氧化黏度增长的润滑油添加剂 |
| CN103848948B (zh) * | 2012-11-30 | 2017-03-22 | 中国石油化工股份有限公司 | 一种部分氢化的三元共聚物及其制备方法和应用 |
| CN104710624B (zh) * | 2013-12-12 | 2017-06-30 | 中国石油化工股份有限公司 | 氢化的星型聚合物及其制备方法以及润滑油组合物和润滑油母料 |
| US9879201B2 (en) * | 2014-02-28 | 2018-01-30 | Cosmo Oil Lubricants Co., Ltd. | Engine oil composition |
| WO2016200783A1 (en) | 2015-06-12 | 2016-12-15 | Kraton Polymers U.S. Llc | A composition for soft skins and uses thereof |
| TWI604027B (zh) | 2015-06-12 | 2017-11-01 | 科騰聚合物美國有限責任公司 | 用於纜線填充應用之熱活化膠 |
| EP3320027B1 (en) | 2015-06-12 | 2020-08-12 | Kraton Polymers U.S. LLC | Styrenic block copolymers as thermally-activated viscosifiers for oilfield applications |
| CN106336490B (zh) * | 2015-07-15 | 2018-11-16 | 中国石油天然气股份有限公司 | 一种氢化苯乙烯双烯共聚物黏度指数改进剂及其制备方法 |
| US10011803B2 (en) * | 2015-12-09 | 2018-07-03 | Infineum International Limited | Viscosity index improver concentrates |
| CN107663265B (zh) * | 2017-08-24 | 2019-11-19 | 中国科学院长春应用化学研究所 | 一种非对称多聚星形聚合物及其制备方法和应用 |
| WO2021132285A1 (ja) * | 2019-12-26 | 2021-07-01 | 株式会社クラレ | 共役ジエン系グラフト重合体からなる粘度指数向上剤、及び油組成物 |
| CN113461881A (zh) * | 2021-06-30 | 2021-10-01 | 沈阳化工研究院有限公司 | 一种在低粘度基础油中原位制备的粘度指数改进剂浓缩液及其制备方法 |
| EP4265678B1 (en) * | 2022-04-22 | 2025-07-09 | Kraton Polymers Nederland B.V. | Hydrogenated styrenic block copolymers and compositions thereof |
| US12281277B2 (en) * | 2023-09-13 | 2025-04-22 | Infineum International Limited | Lubricant compositions containing styrenic block copolymer |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4156673A (en) * | 1976-02-10 | 1979-05-29 | Shell Oil Company | Hydrogenated star-shaped polymer |
| GB1575507A (en) * | 1976-02-10 | 1980-09-24 | Shell Int Research | Hydrogenated star-shaped polymers and oil compositions thereof |
| GB1575449A (en) * | 1976-04-02 | 1980-09-24 | Exxon Research Engineering Co | Hydrogenated tapered-block copolymers of conjegated dienes and vinyl aromatic are useful as oil additives |
| US4242471A (en) * | 1979-08-27 | 1980-12-30 | The Goodyear Tire & Rubber Company | Selectively cyclized block copolymers |
| US4900875A (en) * | 1987-07-10 | 1990-02-13 | Shell Oil Company | Polymeric viscosity index additive and oil composition comprising the same |
| DE3934450A1 (de) * | 1989-10-14 | 1991-04-18 | Basf Ag | Verzweigte copolymerisate |
| US5268427A (en) * | 1990-01-16 | 1993-12-07 | Mobil Oil Corporation | Solid block and random elastomeric copolymers |
| US5070131A (en) * | 1990-09-28 | 1991-12-03 | Shell Oil Company | Gear oil viscosity index improvers |
| EP0541180A3 (en) * | 1991-11-08 | 1993-11-18 | Shell Int Research | Star polymers, a process for their preparation and lubricating oil compositions and concentrates containing them |
| US5360564A (en) * | 1993-07-30 | 1994-11-01 | Shell Oil Company | Dispersant viscosity index improvers |
| US5458796A (en) * | 1994-03-31 | 1995-10-17 | Shell Oil Company | Synthesis of polyisobutylene star-branched polymers via living carbocationic polymerization |
| US5458791A (en) * | 1994-07-01 | 1995-10-17 | Shell Oil Company | Star polymer viscosity index improver for oil compositions |
| US5460739A (en) * | 1994-09-09 | 1995-10-24 | Shell Oil Company | Star polymer viscosity index improver for oil compositions |
-
1999
- 1999-02-16 DE DE69909265T patent/DE69909265T2/de not_active Expired - Lifetime
- 1999-02-16 ES ES99911673T patent/ES2201684T3/es not_active Expired - Lifetime
- 1999-02-16 RU RU2000124095/04A patent/RU2201939C2/ru not_active IP Right Cessation
- 1999-02-16 CN CN99803096A patent/CN1114683C/zh not_active Expired - Lifetime
- 1999-02-16 JP JP2000532489A patent/JP4234325B2/ja not_active Expired - Lifetime
- 1999-02-16 WO PCT/EP1999/001003 patent/WO1999042542A1/en not_active Ceased
- 1999-02-16 EP EP99911673A patent/EP1064347B1/en not_active Expired - Lifetime
- 1999-02-16 CA CA002321006A patent/CA2321006C/en not_active Expired - Lifetime
- 1999-02-16 AU AU30284/99A patent/AU738659B2/en not_active Ceased
- 1999-02-16 KR KR1020007009006A patent/KR100549457B1/ko not_active Expired - Lifetime
- 1999-02-16 BR BRPI9908068-0A patent/BR9908068B1/pt not_active IP Right Cessation
- 1999-02-17 US US09/251,508 patent/US6034042A/en not_active Expired - Lifetime
- 1999-02-23 TW TW088102599A patent/TW428025B/zh not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8716215B2 (en) * | 2005-01-13 | 2014-05-06 | Regenerx Biopharmaceuticals, Inc. | Method of treating or preventing tissue deterioration, injury or damage due to a neuro-, muscular- or neuro-muscular-degenerative disease, or restore tissue adversely affected by said disease |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1064347A1 (en) | 2001-01-03 |
| BR9908068B1 (pt) | 2009-12-01 |
| WO1999042542A1 (en) | 1999-08-26 |
| US6034042A (en) | 2000-03-07 |
| ES2201684T3 (es) | 2004-03-16 |
| CA2321006A1 (en) | 1999-08-26 |
| CA2321006C (en) | 2008-01-22 |
| RU2201939C2 (ru) | 2003-04-10 |
| KR20010024941A (ko) | 2001-03-26 |
| AU3028499A (en) | 1999-09-06 |
| DE69909265D1 (de) | 2003-08-07 |
| CN1291223A (zh) | 2001-04-11 |
| AU738659B2 (en) | 2001-09-20 |
| EP1064347B1 (en) | 2003-07-02 |
| CN1114683C (zh) | 2003-07-16 |
| BR9908068A (pt) | 2000-10-24 |
| JP2002504589A (ja) | 2002-02-12 |
| DE69909265T2 (de) | 2004-02-05 |
| KR100549457B1 (ko) | 2006-02-06 |
| TW428025B (en) | 2001-04-01 |
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