CA1239740A - COPOLYMERS OF .alpha.-.beta.-UNSATURATED DICARBOXYLIC ACID ESTERS, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS LUBRICANTS FOR THE WORKING OF PLASTICS - Google Patents
COPOLYMERS OF .alpha.-.beta.-UNSATURATED DICARBOXYLIC ACID ESTERS, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS LUBRICANTS FOR THE WORKING OF PLASTICSInfo
- Publication number
- CA1239740A CA1239740A CA000411547A CA411547A CA1239740A CA 1239740 A CA1239740 A CA 1239740A CA 000411547 A CA000411547 A CA 000411547A CA 411547 A CA411547 A CA 411547A CA 1239740 A CA1239740 A CA 1239740A
- Authority
- CA
- Canada
- Prior art keywords
- beta
- dicarboxylic acid
- unsaturated dicarboxylic
- copolymers
- olefins
- 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
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 58
- 239000000314 lubricant Substances 0.000 title claims abstract description 21
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 title claims abstract 10
- 238000000034 method Methods 0.000 title claims description 20
- 239000004033 plastic Substances 0.000 title description 8
- 229920003023 plastic Polymers 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001298 alcohols Chemical class 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 238000007046 ethoxylation reaction Methods 0.000 claims abstract description 13
- 238000012545 processing Methods 0.000 claims abstract description 6
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 5
- 229920002994 synthetic fiber Polymers 0.000 claims abstract description 4
- -1 carbon atoms and?-.beta.-unsaturated dicarboxylic acid esters Chemical class 0.000 claims description 17
- 150000002978 peroxides Chemical class 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 15
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000001530 fumaric acid Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 3
- 238000007493 shaping process Methods 0.000 claims description 3
- 229920001169 thermoplastic Polymers 0.000 claims description 3
- 239000004416 thermosoftening plastic Substances 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 150000005690 diesters Chemical class 0.000 claims 1
- 150000002689 maleic acids Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 description 17
- 150000001991 dicarboxylic acids Chemical class 0.000 description 11
- 239000003381 stabilizer Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 241000414967 Colophon Species 0.000 description 3
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 241001481833 Coryphaena hippurus Species 0.000 description 2
- 241001125840 Coryphaenidae Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004605 External Lubricant Substances 0.000 description 1
- 239000004610 Internal Lubricant Substances 0.000 description 1
- 241000570861 Mandragora autumnalis Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—Monomers containing five or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813136931 DE3136931A1 (de) | 1981-09-17 | 1981-09-17 | Copolymere aus (alpha)-(beta)-ungesaettigten dicarbonsaeureestern, verfahren zu deren herstellung sowie deren verwendung als gleitmittel fuer die kunststoffverarbeitung |
| DEP3136931.6 | 1981-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1239740A true CA1239740A (en) | 1988-07-26 |
Family
ID=6141909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000411547A Expired CA1239740A (en) | 1981-09-17 | 1982-09-16 | COPOLYMERS OF .alpha.-.beta.-UNSATURATED DICARBOXYLIC ACID ESTERS, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS LUBRICANTS FOR THE WORKING OF PLASTICS |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4931197A (en, 2012) |
| EP (1) | EP0075216B1 (en, 2012) |
| JP (1) | JPS5861111A (en, 2012) |
| AT (1) | ATE14442T1 (en, 2012) |
| AU (1) | AU551880B2 (en, 2012) |
| CA (1) | CA1239740A (en, 2012) |
| DE (1) | DE3136931A1 (en, 2012) |
| ES (1) | ES515756A0 (en, 2012) |
| ZA (1) | ZA826087B (en, 2012) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5435928A (en) * | 1981-09-17 | 1995-07-25 | Akzo Nobel N.V. | Copolymers from α-β-unsaturated dicarboxylic acid esters, and their use |
| GB2156823B (en) * | 1984-03-22 | 1987-11-25 | Mitsubishi Chem Ind | Wax and ink composition for thermal ink transfer abstract of the disclosure |
| EP0181037B1 (en) * | 1984-11-05 | 1989-08-16 | Akzo N.V. | Metal carboxylate derivative for use in synthetic materials, emulsions and suspensions |
| EP0217585A3 (en) * | 1985-09-24 | 1989-08-30 | Du Pont Canada Inc. | Manufacture of film from linear low density polyethylene |
| CA2004535A1 (en) * | 1988-12-08 | 1990-06-08 | Toru Tagawa | Liquid separating agent |
| JP2741630B2 (ja) * | 1990-11-06 | 1998-04-22 | 株式会社エヌエムビー | セメント組成物の流動性低下防止剤 |
| JP2741631B2 (ja) * | 1990-11-06 | 1998-04-22 | 株式会社エヌエムビー | 流動性低下防止型セメント分散剤 |
| EP0492712A1 (en) * | 1990-12-24 | 1992-07-01 | Akzo Nobel N.V. | Peroxide compositions with ethoxylated water-soluble polymers |
| AU1467292A (en) * | 1991-03-22 | 1992-10-21 | Henkel Corporation | Lubrication for cold forming of metals |
| DE4139601C2 (de) * | 1991-11-30 | 1994-09-08 | Hoechst Ag | Copolymerisate und ihre Verwendung als Gleit- und Trennmittel für die Verarbeitung thermoplastischer Kunststoffe |
| DE4236556A1 (de) * | 1992-10-29 | 1994-05-05 | Stockhausen Chem Fab Gmbh | Verfahren zur Weichmachung/Fettung von Ledern und Pelzen |
| US5274102A (en) * | 1993-02-19 | 1993-12-28 | Akzo Nv | Epoxy functional copolymer of higher α-olefin and unsaturated dicarboxylic acid ester and derivatives thereof |
| US5573702A (en) * | 1993-11-22 | 1996-11-12 | Colgate-Palmolive Co. | Liquid cleaning compositions with grease release agent |
| US5486307A (en) * | 1993-11-22 | 1996-01-23 | Colgate-Palmolive Co. | Liquid cleaning compositions with grease release agent |
| US5446105A (en) * | 1994-02-18 | 1995-08-29 | Akzo Nobel N.V. | Functionalized copolymer of higher α-olefin and unsaturated dicarboxylic acid ester and derivatives thereof |
| US5531912A (en) * | 1994-09-02 | 1996-07-02 | Henkel Corporation | Composition and process for lubricating metal before cold forming |
| US5547595A (en) * | 1995-02-07 | 1996-08-20 | Henkel Corporation | Aqueous lubricant and process for cold forming metal, particularly pointing thick-walled metal tubes |
| EP1144461B1 (en) * | 1999-01-12 | 2004-03-31 | Akzo Nobel N.V. | Aqueous peroxide emulsions |
| DE19901803B4 (de) * | 1999-01-19 | 2005-04-07 | Clariant Gmbh | Copolymere und ihre Verwendung als Additiv zur Verbesserung der Kaltfließeigenschaften von Mitteldestillaten |
| MXPA02005720A (es) * | 1999-12-16 | 2002-09-18 | Akzo Nobel Nv | Composicion encolante. |
| US6444024B1 (en) | 1999-12-16 | 2002-09-03 | Akzo Nobel Nv | Sizing composition |
| US20030017271A1 (en) * | 2001-07-02 | 2003-01-23 | Akzo Nobel N.V. | Pigment composition |
| US7256242B2 (en) * | 2003-06-27 | 2007-08-14 | Chevron Oronite Company, Llc | Esterified copolymers of polyalkenes/unsaturated acidic reagents useful as lubricant and fuel additives |
| JP2007077216A (ja) * | 2005-09-13 | 2007-03-29 | Daido Chem Ind Co Ltd | 鋼板用冷間圧延油組成物 |
| EP2395068A1 (en) | 2011-06-14 | 2011-12-14 | Shell Internationale Research Maatschappij B.V. | Lubricating composition |
| JP5976836B2 (ja) | 2011-12-22 | 2016-08-24 | 昭和シェル石油株式会社 | 潤滑組成物 |
| WO2017083085A1 (en) | 2015-11-13 | 2017-05-18 | Exxonmobil Research And Engineering Company | High viscosity base stock compositions |
| WO2017083086A1 (en) | 2015-11-13 | 2017-05-18 | Exxonmobil Research And Engineering Company | High viscosity base stock compositions |
| CN108473897B (zh) | 2015-11-13 | 2022-01-04 | 埃克森美孚研究工程公司 | 高粘度基础油料组合物 |
| FR3074809B1 (fr) * | 2017-12-11 | 2019-12-13 | Total Marketing Services | Composition de graisse presentant une adhesivite amelioree |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2442558A (en) * | 1944-04-05 | 1948-06-01 | Prophylactic Brush Co | Plasticized copolymers of compounds containing a single ch2=c< group and diesters ofethylene alpha beta dicarboxylic acids |
| US2543964A (en) * | 1947-07-09 | 1951-03-06 | Socony Vacuum Oil Co Inc | Mineral oil compositions containing copolymers of olefins and esters of alpha, beta-unsaturated polybasic acids |
| US2542550A (en) * | 1947-12-31 | 1951-02-20 | Standard Oil Dev Co | Esters of polyether acids and process |
| NL72274C (en, 2012) * | 1949-07-26 | 1952-06-16 | ||
| GB663702A (en) * | 1949-09-10 | 1951-12-27 | Standard Oil Dev Co | Improvements in or relating to copolymers and to lubricant compositions containing them |
| FR1101261A (fr) * | 1954-03-18 | 1955-10-04 | Onera (Off Nat Aerospatiale) | Perfectionnements apportés aux liquides à propriétés lubrifiantes |
| US2978395A (en) * | 1954-10-01 | 1961-04-04 | Exxon Research Engineering Co | Gamma ray polymerization of styrene with unsaturated esters |
| DE1071869B (de) * | 1955-03-09 | 1959-12-24 | Esso Standard Societe Anonyme Frangaise Parrs | Scbmierölzusatlz |
| GB848638A (en) * | 1958-09-03 | 1960-09-21 | Exxon Research Engineering Co | Process of polymerizing compounds possessing a polymerizable double bond |
| DE1645212B2 (de) * | 1963-01-18 | 1975-03-06 | Deutsche Texaco Ag, 2000 Hamburg | Verfahren zur Herstellung thermoplastischer Copolymerisate unter Verwendung von Fumarsäureestern |
| US3197409A (en) * | 1963-03-28 | 1965-07-27 | California Research Corp | Alkylene glycol ester reaction product |
| US3356637A (en) * | 1963-05-27 | 1967-12-05 | Monsanto Co | Vinyl chloride interpolymers and process |
| US3341309A (en) * | 1966-03-11 | 1967-09-12 | Exxon Research Engineering Co | Terpolymer pour point depressant and method of manufacture |
| US3532656A (en) * | 1967-01-19 | 1970-10-06 | Gulf Research Development Co | Ammonium hydroxide polymer solutions for floor polish compositions |
| GB1112749A (en) * | 1967-04-25 | 1968-05-08 | Shell Int Research | Lubricant compositions |
| FR1572843A (en, 2012) * | 1967-07-24 | 1969-06-27 | ||
| US3634052A (en) * | 1968-04-03 | 1972-01-11 | Mobil Oil Corp | Liquid petroleum hydrocarbon compositions containing esters of an alkyl itaconate-maleic anhydride copolymer as fluidity improvers |
| US3642726A (en) * | 1969-08-11 | 1972-02-15 | Gulf Research Development Co | Thermoplastic crosslinked polyester material and method of molding |
| US3642635A (en) * | 1970-03-05 | 1972-02-15 | Exxon Research Engineering Co | Synthetic petrolatum compositions |
| US3705853A (en) * | 1970-09-23 | 1972-12-12 | Mobil Oil Corp | Grease compositions |
| GB1402917A (en) * | 1971-06-30 | 1975-08-13 | Gaf Corp | Partial alkyl and alkoxyalkyl esters and mixed esters of interpolymers of maleic anhydride with unsaturated compounds |
| US3854893A (en) * | 1972-06-14 | 1974-12-17 | Exxon Research Engineering Co | Long side chain polymeric flow improvers for waxy hydrocarbon oils |
| DE2251010C3 (de) * | 1972-10-18 | 1980-02-14 | Basf Ag, 6700 Ludwigshafen | Wachsartige Ester |
| CA1070664A (en) * | 1974-09-16 | 1980-01-29 | Marvin F. Smith (Jr.) | Viscosity index additives for lubricating oils |
| GB1526788A (en) * | 1974-10-17 | 1978-09-27 | Exxon Research Engineering Co | Lubricating compositions |
| DE2639804A1 (de) * | 1975-09-18 | 1977-03-31 | Rohm & Haas | Polymere |
| US4184993A (en) * | 1975-09-18 | 1980-01-22 | Rohm And Haas Company | Plasticizer, plasticized resin composition and process for preparation thereof |
| CA1099047A (en) * | 1977-03-11 | 1981-04-07 | Thomas E. Kiovsky | Epr dispersant vi improver |
| DE2727329C2 (de) * | 1977-06-16 | 1984-03-01 | Akzo Gmbh, 5600 Wuppertal | Olefin-Maleinsäure-Copolymerisat-Ester |
| JPS548132A (en) * | 1977-06-21 | 1979-01-22 | Sumitomo Chem Co Ltd | Preventing composition for corrosion |
| JPS549131A (en) * | 1977-06-22 | 1979-01-23 | Sumitomo Chem Co Ltd | Anti-corrosion composition |
| DE3003797C2 (de) * | 1980-02-02 | 1983-05-11 | Akzo Gmbh, 5600 Wuppertal | Verformung von Gleitmittel enthaltenden Kunststoffen |
-
1981
- 1981-09-17 DE DE19813136931 patent/DE3136931A1/de active Granted
-
1982
- 1982-08-20 ZA ZA826087A patent/ZA826087B/xx unknown
- 1982-09-10 EP EP82108346A patent/EP0075216B1/de not_active Expired
- 1982-09-10 AT AT82108346T patent/ATE14442T1/de not_active IP Right Cessation
- 1982-09-16 ES ES515756A patent/ES515756A0/es active Granted
- 1982-09-16 CA CA000411547A patent/CA1239740A/en not_active Expired
- 1982-09-17 AU AU88515/82A patent/AU551880B2/en not_active Expired
- 1982-09-17 JP JP57161102A patent/JPS5861111A/ja active Granted
-
1988
- 1988-03-04 US US07/168,554 patent/US4931197A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0339094B2 (en, 2012) | 1991-06-12 |
| DE3136931A1 (de) | 1983-04-07 |
| JPS5861111A (ja) | 1983-04-12 |
| DE3136931C2 (en, 2012) | 1990-08-09 |
| ATE14442T1 (de) | 1985-08-15 |
| ES8307846A1 (es) | 1983-07-01 |
| EP0075216B1 (de) | 1985-07-24 |
| ES515756A0 (es) | 1983-07-01 |
| ZA826087B (en) | 1983-07-27 |
| AU551880B2 (en) | 1986-05-15 |
| EP0075216A2 (de) | 1983-03-30 |
| EP0075216A3 (en) | 1983-08-10 |
| AU8851582A (en) | 1983-03-24 |
| US4931197A (en) | 1990-06-05 |
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