DE1618758A1 - Verfahren zur Herstellung von Wachs-Malein-Verbindungen - Google Patents
Verfahren zur Herstellung von Wachs-Malein-VerbindungenInfo
- Publication number
- DE1618758A1 DE1618758A1 DE19671618758 DE1618758A DE1618758A1 DE 1618758 A1 DE1618758 A1 DE 1618758A1 DE 19671618758 DE19671618758 DE 19671618758 DE 1618758 A DE1618758 A DE 1618758A DE 1618758 A1 DE1618758 A1 DE 1618758A1
- Authority
- DE
- Germany
- Prior art keywords
- wax
- maleic
- acid
- compound
- reaction product
- 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.)
- Withdrawn
Links
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- 238000000034 method Methods 0.000 title claims description 20
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- 150000008064 anhydrides Chemical class 0.000 claims description 19
- 230000035515 penetration Effects 0.000 claims description 19
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- 239000002253 acid Substances 0.000 claims description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
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- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- 239000004200 microcrystalline wax Substances 0.000 claims description 3
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- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 claims description 2
- SASYHUDIOGGZCN-ARJAWSKDSA-N (z)-2-ethylbut-2-enedioic acid Chemical compound CC\C(C(O)=O)=C\C(O)=O SASYHUDIOGGZCN-ARJAWSKDSA-N 0.000 claims description 2
- NRSMWHGLCNBZSO-UHFFFAOYSA-N 2-ethylidenebutanedioic acid Chemical compound CC=C(C(O)=O)CC(O)=O NRSMWHGLCNBZSO-UHFFFAOYSA-N 0.000 claims description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 2
- 229940018557 citraconic acid Drugs 0.000 claims 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 claims 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims 1
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- 150000001412 amines Chemical class 0.000 description 8
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- 150000002978 peroxides Chemical class 0.000 description 8
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- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
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- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
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- 239000004071 soot Substances 0.000 description 4
- 229920003261 Durez Polymers 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
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- 230000008878 coupling Effects 0.000 description 3
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- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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- NJMGRJLQRLFQQX-HYXAFXHYSA-N 2-isopropylmaleic acid Chemical compound CC(C)C(\C(O)=O)=C\C(O)=O NJMGRJLQRLFQQX-HYXAFXHYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 239000011888 foil Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940059904 light mineral oil Drugs 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- OBMBYGXRLQQDHH-KVVVOXFISA-N morpholin-4-ium;(z)-octadec-9-enoate Chemical compound C1COCCN1.CCCCCCCC\C=C/CCCCCCCC(O)=O OBMBYGXRLQQDHH-KVVVOXFISA-N 0.000 description 1
- CKIGNOCMDJFFES-UHFFFAOYSA-N n-naphthalen-2-yl-1-phenylmethanimine Chemical compound C=1C=C2C=CC=CC2=CC=1N=CC1=CC=CC=C1 CKIGNOCMDJFFES-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical class ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- CMDGQTVYVAKDNA-UHFFFAOYSA-N propane-1,2,3-triol;hydrate Chemical compound O.OCC(O)CO CMDGQTVYVAKDNA-UHFFFAOYSA-N 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 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
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
- C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
- C07D207/412—Acyclic radicals containing more than six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09G—POLISHING COMPOSITIONS; SKI WAXES
- C09G1/00—Polishing compositions
- C09G1/06—Other polishing compositions
- C09G1/08—Other polishing compositions based on wax
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Duplication Or Marking (AREA)
- Furan Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52707566A | 1966-02-14 | 1966-02-14 | |
| US60787767A | 1967-01-09 | 1967-01-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1618758A1 true DE1618758A1 (de) | 1971-02-25 |
Family
ID=27062304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671618758 Withdrawn DE1618758A1 (de) | 1966-02-14 | 1967-02-07 | Verfahren zur Herstellung von Wachs-Malein-Verbindungen |
Country Status (6)
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3993493A (en) * | 1969-01-03 | 1976-11-23 | Petrolite Corporation | Inks containing isocyanated imides of hydrocarbon anhydrides and blends thereof |
| US3882128A (en) * | 1969-01-03 | 1975-05-06 | Petrolite Corp | Isocyanated imides of hydrocarbon anhydrides and blends thereof |
| JPS5222988B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-08-20 | 1977-06-21 | ||
| US3819386A (en) * | 1971-12-20 | 1974-06-25 | Lubrizol Corp | Rheology modifiers for inks |
| DE2305023A1 (de) * | 1973-02-02 | 1974-08-08 | Basf Ag | Mattierungsmittel fuer lacke |
| US4082558A (en) * | 1974-10-22 | 1978-04-04 | Nippon Oil Co., Ltd. | Novel polyolefin waxes and aqueous polishing emulsions thereof |
| US4118244A (en) * | 1977-06-17 | 1978-10-03 | Gulf Research & Development Company | Paraffin wax composition |
| JPS5481306A (en) * | 1977-12-12 | 1979-06-28 | Nippon Oil Co Ltd | Preparation of oxgen-containing wax |
| US4263209A (en) * | 1979-07-02 | 1981-04-21 | The Dow Chemical Company | Aromatic dianhydrides |
| US4480087A (en) * | 1983-06-30 | 1984-10-30 | Eastman Kodak Company | Polyester waxes based on alkylsuccinic anhydride or alkenylsuccinic anhydride |
| US4481351A (en) * | 1983-06-30 | 1984-11-06 | Eastman Kodak Company | Branched polyester waxes |
| US4483969A (en) * | 1983-06-30 | 1984-11-20 | Eastman Kodak Company | Emulsifiable polyester waxes |
| US4689166A (en) * | 1986-07-17 | 1987-08-25 | Pennzoil Product Company | Succinic acid esters and hydraulic fluids thereform |
| US4784784A (en) * | 1986-07-17 | 1988-11-15 | Pennzoil Products Company | Succinic acid esters and hydraulic fluids therefrom |
| US4720555A (en) * | 1986-09-12 | 1988-01-19 | Pennzoil Products Company | Hydrocarbyl anhydrides |
| US4706702A (en) * | 1986-12-17 | 1987-11-17 | Grasseschi John J | Plumbing sealing system |
| AU632574B2 (en) * | 1989-04-25 | 1993-01-07 | Mobil Oil Corporation | Novel lubricant additives |
| US5290954A (en) * | 1992-08-13 | 1994-03-01 | Eastman Kodak Company | High clarity emulsions containing high melt viscosity maleated polypropylene wax |
| EP0591916A3 (en) * | 1992-10-07 | 1994-05-18 | Roland Man Druckmasch | Printing ink for offset printing |
| US5634971A (en) * | 1995-10-25 | 1997-06-03 | Petrolite Corporation | Process for dispersing pigments with polyoxyalkylated ethers |
| US7501382B2 (en) | 2003-07-07 | 2009-03-10 | Eastman Kodak Company | Slipping layer for dye-donor element used in thermal dye transfer |
| US7071143B2 (en) * | 2004-01-28 | 2006-07-04 | Eastman Kodak Company | Direct thermographic materials with improved protective layers |
| WO2010068675A2 (en) | 2008-12-09 | 2010-06-17 | L'oreal S.A. | Transfer-resistant emulsion containing a surfactant |
| US9308396B2 (en) | 2008-12-16 | 2016-04-12 | L'oreal | Transfer-resistant and long wear foundation in emulsion form containing oil absorbing powders |
| WO2010077940A2 (en) * | 2008-12-16 | 2010-07-08 | Hy Si Bui | Water-insoluble reaction product of a polyamine and an oil-soluble high carbon polar modified polymer |
| EP2305210A3 (en) * | 2009-06-29 | 2011-04-13 | L'oreal S.A. | Composition comprising a sugar silicone surfactant and an oil-soluble polar modified polymer |
| JP2012532110A (ja) | 2009-06-29 | 2012-12-13 | ロレアル | ゲル形態のリフレッシュクリームファンデーション |
| BRPI1002598A2 (pt) * | 2009-06-29 | 2012-03-13 | L'oreal S.A. | Composição e método para a maquilagem dos cílios |
| BRPI1002588A2 (pt) * | 2009-06-29 | 2012-03-13 | L'oreal S.A. | Composição e método de maquilagem de um substrato queratínico |
| EP2322248B1 (en) | 2009-06-29 | 2017-12-27 | L'oreal S.A. | Composition comprising a polyol and an oil-soluble polar modified polymer |
| US8663609B2 (en) * | 2009-06-29 | 2014-03-04 | L'oreal | Composition comprising a polyol, a sugar silicone surfactant and a oil-soluble polar modified polymer |
| BRPI1003178A2 (pt) | 2009-06-29 | 2012-03-20 | L'oreal S.A. | composição |
| US8747868B2 (en) | 2010-12-30 | 2014-06-10 | L'oreal | Reaction product of a polar modified polymer and an alkoxysilane and a composition containing the reaction product |
-
1967
- 1967-01-09 US US607877A patent/US3590076A/en not_active Expired - Lifetime
- 1967-02-02 GB GB5129/67A patent/GB1182161A/en not_active Expired
- 1967-02-07 DE DE19671618758 patent/DE1618758A1/de not_active Withdrawn
- 1967-02-14 NL NL6702236.A patent/NL160583C/xx not_active IP Right Cessation
- 1967-02-14 BE BE694053D patent/BE694053A/xx unknown
- 1967-02-14 JP JP42009508A patent/JPS5147685B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL160583C (nl) | 1979-11-15 |
| NL160583B (nl) | 1979-06-15 |
| BE694053A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-08-14 |
| US3590076A (en) | 1971-06-29 |
| NL6702236A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-08-15 |
| JPS5147685B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-12-16 |
| GB1182161A (en) | 1970-02-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |