CN1890274A - 具有改进冷流性质的燃料油组合物 - Google Patents
具有改进冷流性质的燃料油组合物 Download PDFInfo
- Publication number
- CN1890274A CN1890274A CNA2004800360815A CN200480036081A CN1890274A CN 1890274 A CN1890274 A CN 1890274A CN A2004800360815 A CNA2004800360815 A CN A2004800360815A CN 200480036081 A CN200480036081 A CN 200480036081A CN 1890274 A CN1890274 A CN 1890274A
- Authority
- CN
- China
- Prior art keywords
- polymkeric substance
- fuel
- purposes
- alkyl
- additive
- 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.)
- Granted
Links
- 239000000295 fuel oil Substances 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 title claims description 43
- 239000000654 additive Substances 0.000 claims abstract description 62
- 230000000996 additive effect Effects 0.000 claims abstract description 55
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 16
- 239000000314 lubricant Substances 0.000 claims abstract description 11
- 239000004711 α-olefin Substances 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims description 106
- 239000000446 fuel Substances 0.000 claims description 64
- -1 2-ethylhexyl Chemical group 0.000 claims description 51
- 239000000178 monomer Substances 0.000 claims description 29
- 239000003921 oil Substances 0.000 claims description 25
- 239000002283 diesel fuel Substances 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 15
- 238000007334 copolymerization reaction Methods 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 7
- 239000005864 Sulphur Substances 0.000 claims description 6
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 6
- 239000003747 fuel oil additive Substances 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 239000003350 kerosene Substances 0.000 claims description 5
- 239000003879 lubricant additive Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 238000012856 packing Methods 0.000 claims description 4
- 238000002309 gasification Methods 0.000 claims description 3
- 238000007670 refining Methods 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 2
- 239000002551 biofuel Substances 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- 239000002816 fuel additive Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 abstract description 21
- 150000002148 esters Chemical class 0.000 abstract description 16
- 229920001577 copolymer Polymers 0.000 abstract description 6
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 15
- 239000012188 paraffin wax Substances 0.000 description 15
- 150000001721 carbon Chemical group 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 238000007747 plating Methods 0.000 description 10
- 230000003750 conditioning effect Effects 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000013256 coordination polymer Substances 0.000 description 8
- 150000002830 nitrogen compounds Chemical class 0.000 description 8
- 238000005502 peroxidation Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229910017464 nitrogen compound Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 6
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 230000009183 running Effects 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- 101001018553 Homo sapiens MyoD family inhibitor Proteins 0.000 description 4
- 102100033694 MyoD family inhibitor Human genes 0.000 description 4
- LCJHLOJKAAQLQW-UHFFFAOYSA-N acetic acid;ethane Chemical compound CC.CC(O)=O LCJHLOJKAAQLQW-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- QHZOMAXECYYXGP-UHFFFAOYSA-N ethene;prop-2-enoic acid Chemical compound C=C.OC(=O)C=C QHZOMAXECYYXGP-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 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 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- VKPSKYDESGTTFR-UHFFFAOYSA-N 2,2,4,6,6-pentamethylheptane Chemical compound CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- IQZZFVDIZRWADY-UHFFFAOYSA-N isocoumarin Chemical compound C1=CC=C2C(=O)OC=CC2=C1 IQZZFVDIZRWADY-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical group CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- OEQJOYQHIGIVTN-UHFFFAOYSA-N tert-butyl nonanoate Chemical compound CCCCCCCCC(=O)OC(C)(C)C OEQJOYQHIGIVTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KUKRLSJNTMLPPK-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]hept-2-ene Chemical group C1CC2(C)C=CC1C2(C)C KUKRLSJNTMLPPK-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- GLVKGYRREXOCIB-UHFFFAOYSA-N Bornylene Natural products CC1CCC(C(C)(C)C)C=C1 GLVKGYRREXOCIB-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241001282153 Scopelogadus mizolepis Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical group 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008431 aliphatic amides Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000003225 biodiesel Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000002802 bituminous coal Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 125000003901 ceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- RHMZKSWPMYAOAZ-UHFFFAOYSA-N diethyl peroxide Chemical compound CCOOCC RHMZKSWPMYAOAZ-UHFFFAOYSA-N 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- IGBZOHMCHDADGY-UHFFFAOYSA-N ethenyl 2-ethylhexanoate Chemical group CCCCC(CC)C(=O)OC=C IGBZOHMCHDADGY-UHFFFAOYSA-N 0.000 description 1
- TVFJAZCVMOXQRK-UHFFFAOYSA-N ethenyl 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)OC=C TVFJAZCVMOXQRK-UHFFFAOYSA-N 0.000 description 1
- ZRWACTCEUKFNFM-UHFFFAOYSA-N ethenyl acetate nonanoic acid Chemical compound C(C)(=O)OC=C.C(CCCCCCCC)(=O)O ZRWACTCEUKFNFM-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- LZWYWAIOTBEZFN-UHFFFAOYSA-N ethenyl hexanoate Chemical compound CCCCCC(=O)OC=C LZWYWAIOTBEZFN-UHFFFAOYSA-N 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000002828 fuel tank Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000000755 henicosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002818 heptacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SCFQUKBBGYTJNC-UHFFFAOYSA-N heptyl prop-2-enoate Chemical compound CCCCCCCOC(=O)C=C SCFQUKBBGYTJNC-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000002819 montanyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002465 nonacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 125000005574 norbornylene group Chemical group 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002460 pentacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002469 tricosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
- C10L10/16—Pour-point depressants
-
- 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
-
- 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
- C08F210/02—Ethene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
- C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
-
- 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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
-
- 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
- C10M145/14—Acrylate; Methacrylate
-
- 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
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/03—Narrow molecular weight distribution, i.e. Mw/Mn < 3
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L2250/00—Structural features of fuel components or fuel compositions, either in solid, liquid or gaseous state
- C10L2250/04—Additive or component is a polymer
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L2270/00—Specifically adapted fuels
- C10L2270/02—Specifically adapted fuels for internal combustion engines
- C10L2270/026—Specifically adapted fuels for internal combustion engines for diesel engines, e.g. automobiles, stationary, marine
-
- 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
- C10M2209/084—Acrylate; Methacrylate
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Emergency Medicine (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Lubricants (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
本发明描述了包含共聚的α-烯烃、乙烯基酯和α,β-不饱和羧酸酯的聚合物用作燃料油和润滑剂的添加剂的用途,特别是用作燃料油的冷流改进剂的用途。此外,还描述了添加有这些聚合物的燃料油和润滑剂;以及包含这种聚合物的添加剂包装体。
Description
本发明涉及包含共聚的α-烯烃、乙烯基酯和α,β-不饱和羧酸酯的聚合物作为燃料油和润滑剂的添加剂,特别是作为燃料的冷流改进剂的用途;还涉及添加有这些聚合物的燃料油和润滑剂;以及包含这种聚合物的添加剂包装体。
现有技术
温度降低时,包括石蜡,例如中间馏分、柴油和燃料油的矿物油在流动性方面表现出明显的劣化。引起上述情况的原因是较长链的石蜡从浊点温度开始发生结晶,形成大的片状石蜡晶体。这些石蜡晶体具有海绵状结构,导致其它燃料组分混入该晶体结构中。这些晶体的出现很快就导致油箱和机动车辆中的燃料过滤器堵塞。在低于倾点(PP)的温度下,燃料最终不再流动。
为减轻这些问题,一段时间以来,已经在其中添加少量的燃料添加剂,该添加剂经常由用于非常小的石蜡晶体早期形成的成核剂和实际的冷流改进剂(也称为CFI或MDFI)的组合组成。这些物质表现出和燃料中的石蜡类似的结晶特性,但抑制了它们生长,使得与未经添加的燃料相比,其可以在明显较低的温度下通过过滤器。冷滤堵塞点(CFPP)被确定为其量度。其它可用的添加剂是蜡防沉添加剂(WASA),其防止非常小的晶体在燃料中沉积。
根据基础燃料和添加剂的组成,冷流改进剂的添加量为约50-500ppm。现有技术公开了各种CFI产品(参见例如US-A-3,038,479,3,627,838和3,961,961,EP-A-0,261,957或DE-A-31 41 507和25 15 805)。普通的CFI通常是聚合化合物,特别是乙烯-乙酸乙烯酯(EVA)共聚物,例如BASF AG所售的商品名为Keroflux的产品。
常规CFI和润滑改进剂(单-或多元羧酸与单-或多元醇的酯)的组合也被描述为改进的CFI组合(EP-A-0 721 492)。
EP 0922716描述了一种制备三元共聚物的方法,该共聚物除乙烯之外,包含共聚的至少两种其它烯键式不饱和化合物,例如乙烯基酯、丙烯酸酯或甲基丙烯酸酯、烷基乙烯基醚或高级烯烃。据说它们适合作为矿物油馏分的流动点改进剂。
DE 1902925描述了三元共聚物,其包含共聚的乙烯、例如乙酸乙烯酯的短链羧酸的乙烯基酯和长链不饱和单体,例如长链羧酸的乙烯基酯或由长链醇衍生的丙烯酸酯。据说这些物质降低了中间馏分的倾点并改进了它们的过滤性。
US4,156,434描述了三元共聚物,其除了乙烯和乙酸乙烯酯之外,包含共聚的由C12-C24醇衍生的丙烯酸酯。据说这些物质降低了气油的倾点。其中没有描述到改进过滤性的作用。
仍有一种对具有CFI性能的其它添加剂的持续需要,特别是那些使用成本更便宜的添加剂,例如因为它们在比商业CFI更低的剂量下改进燃料油或润滑剂的冷流性能,特别是燃料油的过滤性。
本发明的简要描述
因此本发明的目的是提供新型的这种添加剂。
令人惊讶地,意外的观察结果实现了该目的,该观察结果是包含共聚的α-烯烃、乙烯基酯和α,β-不饱和羧酸酯的聚合物可以用作CFI添加剂,并且还具有比常规EVA-CFI更好的性能。
因此本发明首先涉及包含共聚的α-烯烃、乙烯基酯和α,β-不饱和羧酸酯的聚合物用作燃料油和润滑剂的添加剂的用途。特别地,所用聚合物是那些包含无规分布共聚的乙烯基酯和α,β-不饱和羧酸酯的聚合物。该聚合物优选是基本由上述三种单体构成的三元共聚物。
优选使用的聚合物由包括单体M1、M2和M3的这些单体构成,其中M1、M2和M3具有如下通式:
其中
R1是H或C1-C40烃基,例如C1-C20烃基,特别是C1-C10烃基,优选是C1-C4烃基;
R2、R3和R4各自独立地是H或C1-C4烷基;
R5是C1-C20烃基;
R6、R7和R8各自独立地是H或C1-C4烷基;和
R9是C1-C20烃基。
单体M1、M2和M3在本发明所用的聚合物中的存在量可以是聚合物中的以下摩尔比Mx/(M1+M2+M3):
M1:从0.60到0.98,优选从0.7到0.95,特别是从0.8到0.9;
M2:从0.01到0.20,优选从0.015到0.17,特别是从0.02到0.16;
M3:从0.01到0.20,优选从0.02到0.15,特别是从0.03到0.1,尤其是从0.03到0.09。
R1优选是H、甲基或乙基,特别是H;换句话说,单体M1优选是乙烯、丙烯或1-丁烯,特别是乙烯。
在单体M2中,R2、R3和R4基优选各自是H或甲基。更优选地,R2、R3和R4基其中两个都是H,另一基团是H或甲基。特别地,R2、R3和R4三个基团都是H。
R5优选是C1-C12烃基,特别优选的是C1-C10烃基,更优选是C1-C9烃基,还更优选的是C4-C8烃基。烃基优选是烷基。特别地,R5是正丁基、2-乙基己基或十二烷基,其中较优选的是正丁基和2-乙基己基,特别是2-乙基己基。
单体M2优选选自丙烯酸正丁酯、丙烯酸2-乙基己酯和丙烯酸十二烷基酯,更优选选自丙烯酸正丁酯和丙烯酸2-乙基己酯。特别地,它是丙烯酸2-乙基己酯。
在单体M3中,R6、R7和R8各自独立地优选是H或甲基,更优选是H。
R9优选是C1-C10烃基。烃基优选是烷基。R9更优选是乙基或甲基,特别是甲基。
单体M3更优选是乙酸乙烯酯。
本发明所用的聚合物优选是通过单体M1、M2和M3的优选自由基聚合,特别是高压聚合获得的。
优选所用的聚合物选自乙烯/丙烯酸正丁酯/乙酸乙烯酯聚合物、乙烯/丙烯酸2-乙基己酯/乙酸乙烯酯聚合物和乙烯/丙烯酸十二烷基酯/乙酸乙烯酯聚合物,特别优选是以上最先提及的两种聚合物。特别地,使用乙烯/丙烯酸2-乙基己酯/乙酸乙烯酯聚合物。
优选使用所述聚合物作为冷流改进剂。
上述聚合物以足够在添加的燃料或润滑剂中表现出作为冷流改进剂作用的量单独使用或与其它这种聚合物组合使用。
本发明进一步提供了燃料油组合物,其包含大部分重量比例的沸程为120-500℃的中间馏分燃料和较小重量比例的至少一种如上定义的本发明中所用的聚合物(冷流改进剂)。
这样的燃料油组合物还可以包含0-100重量%,优选0-30重量%的生物柴油(biodiesel)(来自动物和/或植物生产中)作为燃料组分。
优选的燃料油组合物选自柴油燃料、煤油和燃料油,并且柴油燃料可以通过精炼、煤炭气化或气体液化获得,或者可以是这种产品的混合物并可以任选地与可再生的燃料混合。优选是那些其中混合物的硫含量优选为至多500ppm的燃料油组合物。
本发明进一步提供了润滑剂组合物,其包含主要重量比例的常规润滑剂和较小重量比例的至少一种如上定义的聚合物。
在本发明的范围中,本发明所用的聚合物可以结合其它常规冷流改进剂和/或其它润滑剂和燃料油添加剂使用。
本发明最后还涉及添加剂包装体,其包含至少一种如上定义的本发明中所用的聚合物和至少一种其它常规润滑剂和燃料油添加剂。
本发明的详细描述
a)本发明中所用的聚合物
本发明中所用的聚合物优选基本由如上定义的单体M1、M2和M3构成。制备的结果是用作调节剂(链终止剂)的痕量化合物有时可能存在。
当没有给出其它信息时,下面的一般定义适用:
C1-C40烃基特别是C1-C40烷基,例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、戊基、己基、庚基、辛基、2-乙基己基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基、二十烷基、二十一烷基(hencosyl)、二十二烷基、二十三烷基、二十四烷基、二十五烷基、二十六烷基、二十七烷基、二十八烷基、二十九烷基、squalyl和高级同系物以及相应的位置异构体。这同样适用于C1-C20烃基。C1-C9烃基特别是C1-C9烷基,例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、戊基、新戊基、己基、庚基、辛基、新辛基、2-乙基己基、壬基和新壬基。另外,C1-C10烃基还特别是癸基和新癸基。C4-C8烃基特别是C4-C8烷基,例如正丁基、仲丁基、异丁基、叔丁基、戊基、己基、庚基、辛基和2-乙基己基。
合适单体M1的例子包括:具有非末端的或优选末端双键的单烯烃,特别是乙烯、丙烯、1-丁烯、1-戊烯、1-己烯、1-庚烯、1-辛烯、1-壬烯和1-癸烯,以及具有至多40个碳原子的高级单不饱和同系物。
优选的α,β-不饱和羧酸酯M2的例子包括:C1-C20链烷醇的丙烯酸酯,例如丙烯酸甲酯、丙烯酸乙酯、丙烯酸丙酯、丙烯酸异丙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸叔丁酯、丙烯酸正戊酯、丙烯酸新戊酯、丙烯酸己酯、丙烯酸庚酯、丙烯酸辛酯、丙烯酸新辛酯、丙烯酸2-乙基己酯、丙烯酸壬酯、丙烯酸新壬酯、丙烯酸癸酯、丙烯酸新癸酯、丙烯酸十二烷基酯、丙烯酸棕榈基酯和丙烯酸十八烷基酯;以及相应的甲基丙烯酸酯、丁烯酸酯和异丁烯酸酯,其中优选丙烯酸酯。
合适单体M3的例子包括:
C1-C20羧酸乙烯基酯,特别是乙酸、丙酸、丁酸、戊酸、异戊酸、新戊酸、己酸、庚酸、辛酸、壬酸、新壬酸、新癸酸、癸酸、月桂酸、十四烷酸、棕榈酸、硬脂酸和花生酸的乙烯基酯;以及相应的丙烯基酯。然而,优选是乙烯基酯。
本发明聚合物的数均分子量Mn为约1000-20 000,更优选为1000-10000,特别为1500-6000,尤其为1500-5000。
该聚合物的重均分子量Mw可以为100-30 000,特别是2000-20 000,和/或Mw/Mn的比率为1.5-5.0,优选为1.8-4.0,特别为1.9-3.5。
特别优选的聚合物由单体乙烯、乙酸乙烯酯和丙烯酸酯单体组成,其中丙烯酸酯单体选自丙烯酸正丁酯、丙烯酸2-乙基己酯和丙烯酸十二烷基酯,优选选自丙烯酸正丁酯和丙烯酸2-乙基己酯。特别地,丙烯酸酯单体是丙烯酸2-乙基己酯。
基于由乙烯、丙烯酸2-乙基己酯(EHA)和乙酸乙烯酯(VAC)组成的聚合物,各单体的重量比例为:
EHA:4-80重量%,优选5-62重量%,特别是约7-45重量%
VAC:1-42重量%,优选1-30重量%,特别是约1-25重量%,尤其是1-20重量%
这种聚合物的粘度(Ubbelohde DIN 51562测定)在约120℃的温度下为约5-25000mm2/s,优选约10-1000mm2/s,特别是约50-700mm2/s。
b)聚合物的制备
本发明的聚合物通过本身已知的方法,优选通过现有技术已知的用于不饱和化和物的直接自由基高压共聚制得(参见例如Ullmann’sEncyclopedia of Industrial Chemistry,第5版,“石蜡”,第A28卷,第146ff.页,VCH,Weinheim,Basle,Cambridge,New York,Tokyo,1996;和US3,627,838;DE-A 2515805;DE-A3141507;EP-A 0007590),。
共聚物的制备优选在搅拌高压釜或高压搅拌反应器或二者组合中进行。在该装置中,长度/直径的比主要保持为5∶1-30∶1,优选为10∶1-20∶1。
对于聚合反应,合适的压力条件是1000-3000巴,优选1500-2000巴。反应温度例如为160-320℃,优选为200-280℃。
用来控制共聚物分子量的调节剂是例如通式I的脂族醛或脂族酮:
或其混合物。
在该式中,Ra和Rb基相同或不同,并选自
-氢;
-C1-C6烷基,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、仲戊基、新戊基、1,2-二甲基丙基、异戊基、正己基、异己基、仲己基;更优选是C1-C4烷基,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基和叔丁基;
-C3-C12环烷基,例如环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基、环癸基、环十一烷基和环十二烷基;优选是环戊基、环己基和环庚基。
Ra和Rb基也可以彼此共价键合以形成4-13元环。例如,Ra和Rb一起可以形成下述的亚烷基:-(CH2)4-、-(CH2)5-、-(CH2)6-、-(CH2)7-、-CH(CH3)-CH2-CH2-CH(CH3)-或-CH(CH3)-CH2-CH2-CH2-CH(CH3)-。
非常特别优选的是使用丙醛或乙基甲基甲酮作为调节剂。
其它非常合适的调节剂是未支化的脂族烃,例如丙烷,或具有叔氢原子的支化脂族烃,例如异丁烷、异戊烷、异辛烷或异十二烷(2,2,4,6,6-五甲基庚烷)。其它可以使用的调节剂是高级烯烃,如丙烯。
同样优选的是以上调节剂与氢气的混合物或仅用氢气。
所用调节剂的量对应于高压聚合方法中的常用量。
用于自由基聚合反应的有用引发剂是常用的自由基引发剂,例如有机过氧化物、氧或偶氮化合物。同样合适的是多种自由基引发剂的混合物。有用的自由基引发剂包括例如一种或多种选自下述可商购物质的过氧化物:
-过氧化二癸酰、2,5-二甲基-2,5-二(过氧化2-乙基己酰)己烷、过氧化2-乙基己酸叔戊酯、过氧化二苯甲酰、过氧化2-乙基己酸叔丁酯、过氧化二乙基乙酸叔丁酯、过氧化二乙基异丁酸叔丁酯、作为异构体混合物的1,4-二(叔丁基过氧化碳酰)环己烷、过氧化异壬酸叔丁酯、1,1-二(过氧化叔丁基)-3,3,5-三甲基环己烷、1,1-二(过氧化叔丁基)环己烷、过氧化甲基异丁基酮、过氧化异丙基碳酸叔丁酯、2,2-二(过氧化叔丁基)丁烷或过氧化乙酸叔丁酯;
-叔丁基过氧化苯甲酸酯、过氧化二叔戊基、过氧化二异丙苯基、异构的二(叔丁基过氧化异丙基)苯、2,5-二甲基-2,5-二叔丁基过氧化己烷、叔丁基异丙苯基过氧化物、2,5-二甲基-2,5-二(过氧化叔丁基)己-3-炔、过氧化二叔丁基、1,3-二异丙基单氢过氧化物、异丙苯过氧化氢或叔丁基过氧化氢;或
-二聚或三聚的过氧化酮,如EP-A-0 813 550所公开的。
特别合适的过氧化物是过氧化二叔丁基、过氧化新戊酸叔丁酯、过氧化异壬酸叔丁酯或过氧化二苯甲酰或其混合物。偶氮化合物的例子是偶氮二异丁腈(AIBN)。这些自由基引发剂以用于聚合反应的常用量使用。
在一种优选的方法中,本发明聚合物是通过这样的方式制得的:单体M1、M2和M3的混合物在调节剂的存在下,在约20-50℃、例如30℃的温度下,优选连续地通过搅拌高压釜,该高压釜保持在约1500-2000巴,例如约1700巴的压力下。优选连续加入通常溶解在合适溶剂(例如异十二烷)中的引发剂使得反应器中的温度保持在期望的反应温度,例如200-250℃。反应混合物解压后获得的聚合物然后以常规的方式分离出。
对这种方法进行改进当然是可能的,并且可以由本领域技术人员无需过度劳动来完成。例如,共聚单体和调节剂可分开地计量到反应混合物中,或反应温度可以在工艺过程中变化,这里仅列举了少数实例。
c)燃料油组合物
根据本发明,燃料油组合物优选是燃料。合适的燃料是汽油燃料和中间馏分,例如柴油燃料、燃料油或煤油,特别优选的是柴油燃料和燃料油。
燃料油是例如低硫或高硫的原油残液或烟煤或褐煤的馏分,其通常具有150-400℃的沸程。燃料油优选是低硫燃料油,例如那些硫含量至多0.1重量%,优选至多0.05重量%,更优选至多0.005重量%,特别是至多0.001重量%的燃料油。燃料油的例子特别是用于家用燃油集中供热或EL燃料油的燃料油。这种燃料油的质量要求例如在DIN 51-603-1中有拟定,的(同样参见Ullmann’s Encyclopedia of Industrial Chemistry,第5版,第A12卷,第617ff.页,通过引用将其内容结合于此)。
柴油燃料是例如通常具有100-400℃沸程的原油残液。这些物质通常是在高达360℃或更高的温度下蒸馏出95%的馏分。但是,它们也可以是“超低硫化柴油”或“城市柴油”,其特征在于蒸馏出95%时最高温度为例如345℃,并且最大硫含量为0.005重量%,或者蒸馏出95%时温度为例如285℃,并且最大硫含量为0.001重量%。除通过精炼可获得的柴油燃料之外,同样合适的有那些通过煤气化或气体液化(气至液(GTL)燃料)可获得的柴油燃料。可再生燃料也是合适的,例如生物柴油或生物乙醇、其混合物或可再生燃料与上述柴油燃料的混合物。
特别优选的是使用本发明的添加剂来添加具有低硫含量的柴油燃料,也就是硫含量低于0.05重量%,优选低于0.02重量%,特别低于0.005重量%,尤其低于0.001重量%,或者用于添加低硫含量的燃料油,例如硫含量至多0.1重量%、优选至多0.05重量%、例如至多0.005重量%或例如至多0.001重量%。
优选地,本发明添加剂的使用比例是基于燃料油组合物总量,其本身要基本足以影响燃料油组合物的冷流性能。特别优选的是基于燃料油组合物的总量,以0.001-1重量%、更优选0.01-0.15重量%,特别是0.01-0.1重量%的量使用添加剂。
d)共添加剂
本发明的聚合物可以单独地或作为这种聚合物与任选的其它本身已知的添加剂的混合物添加到燃料油组合物中。
除本发明的聚合物之外,根据本发明可以存在于燃料油中的特别是用作柴油燃料和燃料油的合适添加剂包括清净剂、阻蚀剂、去雾剂、破乳剂、防沫剂、抗氧化剂、金属减活剂、多功能稳定剂、十六烷值改进剂、燃烧促进剂、染料、指示剂、增溶剂、抗静电剂、润滑改进剂以及其它改进燃料冷流性能的添加剂,例如成核剂、其它常规流动性改进剂(MDFI)、石蜡分散剂(WASA)和所提到的后两种添加剂的组合(同样参见Ullmann’sEncyclopedia of Industrial Chemistry,第5版,第A16卷,第719ff页;或起先引用的关于冷流改进剂的专利)。
其它常规冷流改进剂特别是:
(a)不同于本发明所用聚合物的、乙烯与至少一种其它烯键式不饱和单体的共聚物;
(b)梳形聚合物;
(c)聚氧化烯;
(d)极性氮化合物;
(e)硫代羧酸或磺酸或它们的衍生物;和
(f)聚(甲基)丙烯酸酯。
在乙烯与至少一种其它烯键式不饱和单体的共聚物(a)中,单体优选选自链烯基羧酸酯、(甲基)丙烯酸酯和烯烃。
合适的烯烃是例如那些具有3-10个碳原子且具有1-3个、优选1或2个、特别是1个碳碳双键的烯烃。在后一情况下,碳碳双键可以在端部(α-烯烃)或在内部。但是,优选α-烯烃,特别优选具有3-6个碳原子的α-烯烃,例如丙烯、1-丁烯、1-戊烯和1-己烯。
合适的(甲基)丙烯酸酯是例如(甲基)丙烯酸与C1-C10链烷醇,特别是与甲醇、乙醇、丙醇、异丙醇、正丁醇、仲丁醇、异丁醇、叔丁醇、戊醇、己醇、庚醇、辛醇、2-乙基己醇、壬醇和癸醇的酯。
合适的链烯基羧酸酯是例如具有2-20个碳原子的、其烃基可以是线性的或支化的羧酸的乙烯基酯和丙烯基酯。其中,优选是乙烯基酯。在具有支化烃基的羧酸中,优选是那些支链分布在相对于羧基的位上的羧酸,特别优选是α-碳原子是叔碳原子的羧酸,即羧酸是新羧酸。但是,优选羧酸的烃基是线性的。
合适的链烯基羧酸酯的例子是乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯、2-乙基己酸乙烯酯、新戊酸乙烯酯、己酸乙烯酯、新壬酸乙烯酯、新癸酸乙烯酯和相应的丙烯基酯,但是优选的是乙烯基酯。特别优选的链烯基羧酸酯是乙酸乙烯酯。
特别优选的烯键式不饱和单体选自链烯基羧酸酯。
还合适的有包含两种或更多种不同的共聚链烯基羧酸酯的共聚物,这些链烯基羧酸酯的区别在于链烯基和/或羧酸基。同样合适的是除了链烯基羧酸酯之外,包含至少一种共聚烯烃和/或至少一种共聚(甲基)丙烯酸酯的共聚物。
该共聚物中共聚的烯键式不饱和单体的量以整个共聚物为基准优选为1-50mol%,更优选10-50mol%,特别是5-20mol%。
共聚物(a)优选具有1000-20 000,更优选1000-10 000,特别是1000-6000的数均分子量Mn。
梳形共聚物(b)例如是那些在“Comb-Like Polymers,Structure andProperties”,N.A.Platéand V.P.Shibaev,J.Poly.Sci.Macromolecular Revs.8,第117-253页(1974)中描述的。在上述的梳形共聚物中,合适的梳形聚合物是例如式II表示的那些:
其中
D是R17、COOR17、OCOR17、R18、OCOR18或OR17,
E是H、CH3、D或R18,
G是H或D,
J是H、R18、R18COOR17、芳基或杂环基,
K是H、COOR18、OCOR18、OR18或COOH,
L是H、R18、COOR18、OCOR18、COOH或芳基,
其中
R17是具有至少10个碳原子,优选具有10-30个碳原子的烃基,
R18是具有至少一个碳原子,优选具有1-30个碳原子的烃基。
m是1.0-0.4的摩尔分率和
n是0-0.6的摩尔分率。
优选的梳形聚合物是例如可通过将马来酸酐或富马酸与另一种烯键式不饱和单体,例如与α-烯烃或不饱和酯,例如乙酸乙烯酯共聚,随后使酸酐或酸官能团与具有至少10个碳原子的醇酯化而获得的。其它优选的梳形聚合物是α-烯烃和酯化的共聚单体的共聚物,例如苯乙烯和马来酸酐的酯化共聚物或苯乙烯和富马酸的酯化共聚物。同样合适的是梳形聚合物的混合物。梳形聚合物也可以是聚富马酸酯或聚马来酸酯。乙烯醚的均聚物和共聚物也是合适的梳形聚合物。
合适的聚氧化烯(c)是例如聚氧化烯酯、醚、酯/醚及其混合物。聚氧化烯化合物优选包含至少一个、更优选至少两个具有10-30个碳原子的线性烷基和分子量至多为5000的聚氧化烯基。聚氧化烯基的烷基优选包含1-4个碳原子。这样的聚氧化烯化合物描述在例如EP-A-0 061 895和US4,491,455中,通过引入将其全部内容引用于此。优选的聚氧化烯酯、醚和酯/醚具有通式III:
其中
R19和R20各自独立地是R21、R21-CO-、R21-O-CO(CH2)z-或R21-O-CO(CH2)z-CO-,其中R21是线性的C1-C30烷基,
y是1-4的数,
x是2-200的数,和
z是1-4的数。
通式II中R19和R20都是R21的优选聚氧化烯化合物是数均分子量为100-5000的聚乙二醇和聚丙二醇。通式III中R19和R20基中其中一个是R21、另一个是R21-CO-的优选聚氧化烯是具有10-30个碳原子的脂肪酸,例如硬脂酸或山嵛酸的聚氧化烯酯。其中R19和R20都是R21-CO-基的优选聚氧化烯化合物是具有10-30个碳原子的脂肪酸,例如硬脂酸或山嵛酸的二酯。
极性氮化合物(d)有利地是油溶性的,可以是离子的或非离子的,并且优选具有至少一个、更优选具有至少两个式>NR22的取代基,其中R22是C8-C40烃基。氮取代基也可以是季铵化的,即呈阳离子形式。这样的氮化合物的例子是通过使至少一种被至少一个烃基所取代的胺与具有1-4个羧基的羧酸或其合适的衍生物反应获得的铵盐和/或酰胺。胺优选包含至少一个线性的C8-C40烷基。合适的伯胺是例如辛胺、壬胺、癸胺、十一烷基胺、十二烷基胺、十四烷基胺和高级的线性同系物。合适的仲胺是例如二-十八烷基胺和甲基二十二烷基胺。同样合适的是胺混合物,特别是工业规模上获得的胺混合物,例如脂肪胺或氢化的高级胺(tallamines),如Ullmann’s Encyclopedia of Industrial Chemistry,第6版,2000电子出版物,“胺,脂族”章中所述的。适合反应的酸是例如被长链烃基取代的丁二酸、环己烷-1,2-二羧酸、环己烯-1,2-二羧酸、环戊烷-1,2-二羧酸、萘基二羧酸、邻苯二甲酸、间苯二甲酸和对苯二甲酸。
极性氮化合物的其它例子是那些具有至少两个式-A-NR23R24取代基的环系化合物,其中A是线性或支化的、任选被一个或多个选自O、S、NR35和CO的基团间隔的脂族烃基,R23和R24各自是任选地被一个或多个选自O、S、NR35和CO的基团间隔和/或被一个或多个选自OH、SH和NR35R36取代基取代的C9-C40烃基,其中R35是任选地被一个或多个选自CO、NR35、O和S的部分所取代和/或被一个或多个选自NR37R38、OR37、SR37、COR37、COOR37、CONR37R38、芳基或杂环基的基团所取代的C1-C40烷基,其中R37和R38各自独立地选自H或C1-C4烷基;R36是H或R35。
A优选是亚甲基或具有2-20个亚甲基单元的多亚甲基。合适的R23和R24基的例子是2-羟乙基、3-羟丙基、4-羟丁基、2-酮丙基、乙氧基乙基和丙氧基丙基。环系可以是同素环、杂环、稠合的多环或非稠合的多环体系。环系优选是芳族碳环或芳族杂环,特别是芳族碳环。这种多环环系的例子是稠合的苯型结构,例如萘、蒽、菲和芘;稠合的非苯型结构,例如甘菊环、茚、二氢化茚和芴;非稠合的多环,例如二苯基;杂环,例如喹啉、吲哚、吲哚满、苯并呋喃、香豆素、异香豆素、苯并噻吩、咔唑、二苯并呋喃和二亚苯基硫化物;非芳族的或部分饱和的环系,例如萘烷;以及三维结构,例如α-蒎烯、莰烯、冰片烯、降莰烷、降冰片烯、二环辛烷和二环辛烯。
合适极性氮化合物的其它例子是长链伯或仲胺与含羧基的聚合物的缩合物。
在此提及的极性氮化合物在WO 00/44857以及其中引用的参考文献中有描述,通过引用将其全部内容包含于此。
合适的极性氮化合物在例如DE-A-198 48 621和DE-A-196 22 052或EP-B 398 101中也有描述,通过引用将其内容包含于此。
合适的硫代羧酸/磺酸或它们的衍生物是例如通式IV的那些:
其中
Y是SO3 -(NR25 3R26)+、SO3 -(NHR25 2R26)+、SO3 -(NH2R25R26)、SO3 -(NH3R26)或SO2NR25R26,
X是Y、CONR25R27、CO2 -(NR25 3R27)+、CO2 -(NHR25 2R27)+、R28-COOR27、NR25COR27、R28OR27、R28OCOR27、R28R27、N(COR25)R27或Z-(NR25 3R27),
其中
R25是烃基,
R26和R27各自是主链上具有至少10碳原子的烷基、烷氧基烷基或聚烷氧基烷基;
R28是C2-C5亚烷基,
Z-是一个阴离子当量,和
A和B各自是烷基、链烯基或是两个经取代的烃基,或与它们键合的碳原子一起形成芳族或脂环族的环系。
这种硫代羧酸和磺酸以及它们的衍生物在EP-A-0 261 957中有描述,通过引用将其全部内容包含于此。
合适的聚(甲基)丙烯酸酯(f)是丙烯酸酯和甲基丙烯酸酯的均聚物或共聚物。优选是C1-C40醇衍生的丙烯酸酯均聚物。优选的是至少两种不同(被酯化的醇不同)的(甲基)丙烯酸酯的共聚物。任选地,共聚物包含另一种不同的共聚烯键式不饱和单体。该聚合物的重均分子量优选是50000-500 000。特别优选的聚合物是甲基丙烯酸与饱和的C14-和C15-醇的甲基丙烯酸酯的共聚物,其中酸基已被氢化的高级胺中和。合适的聚(甲基)丙烯酸酯在例如WO 00/44857中有描述,通过引用将其全部内容包含于此。
e)添加剂包装体
本申请最后提供了一种添加剂浓缩物,其包含如上定义的本发明的聚合物和至少一种稀释剂以及任选的至少一种其它添加剂、特别是选自以上共添加剂的添加剂。
合适的稀释剂是例如来自原油加工的馏分,例如煤油、石脑油或光亮油。同样合适的是芳烃和脂族烃和烷氧基链烷醇。在中间馏分的情况下,特别是在柴油燃料和燃料油的情况下,优选使用的稀释剂是石脑油、煤油、柴油燃料、芳烃,例如Solvent Naphtha heavy,Solvesso或Shellsol以及这些溶剂和稀释剂的混合物。
本发明的共聚物在该浓缩物中的存在量基于浓缩物的总重量优选为0.1-80重量%,更优选1-70重量%,特别是20-60重量%。
现在将参照下面非限制性的实施例来详细地说明本发明。
实验部分:
制备实施例1-23
通过乙烯、丙烯酸2-乙基己酯(EHA)和乙酸乙烯酯(VAC)的高压聚合制得共23种不同的本发明聚合物。
表1比较了下面测试实施例中所用的聚合物的性质。
乙烯、EHA和VAC在所得聚合物中的含量通过NMR光谱测定。粘度通过Ubbelohde DIN 51562测定。
表1
聚合物编号 | E[Mol%] | VAC[Mol%] | EHA[Mol%] | 粘度[mm2/s] | Mn | Mw | Mw/Mn |
1 | 88.0 | 4.2 | 7.8 | 60 | 2088 | 4189 | 2.01 |
2 | 88.0 | 4.4 | 7.6 | 150 | 2959 | 6666 | 2.25 |
3 | 88.1 | 4.4 | 7.5 | 605 | 4635 | 12811 | 2.76 |
4 | 86.6 | 3.9 | 9.5 | 60 | 2124 | 4285 | 2.02 |
5 | 86.4 | 4.3 | 9.3 | 150 | 3022 | 6754 | 2.23 |
6 | 86.4 | 4.1 | 9.5 | 595 | 4797 | 13238 | 2.76 |
7 | 83.8 | 4.1 | 12.1 | 60 | 2064 | 4280 | 2.07 |
8 | 83.2 | 4.4 | 12.4 | 150 | 2994 | 7203 | 2.41 |
9 | 83.1 | 4.4 | 12.5 | 600 | 4744 | 14503 | 3.06 |
10 | 80.2 | 4.5 | 15.3 | 150 | 3038 | 7279 | 2.40 |
11 | 80.4 | 4.1 | 15.5 | 600 | 4681 | 15697 | 3.35 |
12 | 89.6 | 8.0 | 2.4 | 60 | 1977 | 3910 | 1.98 |
13 | 89.8 | 7.9 | 2.3 | 150 | 2831 | 6212 | 2.19 |
14 | 89.2 | 8.2 | 2.6 | 605 | 3862 | 11098 | 2.87 |
15 | 89.8 | 8.4 | 4.8 | 60 | 1928 | 3902 | 2.02 |
16 | 86.5 | 8.4 | 5.1 | 150 | 2926 | 6337 | 2.17 |
17 | 86.3 | 8.5 | 5.2 | 620 | 4613 | 12019 | 2.61 |
18 | 84.2 | 8.1 | 7.7 | 60 | 2003 | 4025 | 2.01 |
19 | 83.1 | 8.7 | 8.2 | 150 | 2855 | 6382 | 2.24 |
20 | 84.3 | 8.0 | 7.7 | 615 | 4858 | 13061 | 2.69 |
21 | 81.1 | 7.9 | 11.0 | 60 | 2100 | 4276 | 2.04 |
22 | 80.8 | 8.0 | 11.2 | 150 | 2878 | 6634 | 2.31 |
23 | 81.1 | 7.6 | 11.3 | 630 | 4774 | 14263 | 2.99 |
E:乙烯
EHA:丙烯酸2-乙基己酯
VAC:乙酸乙烯酯
b)测试实施例1-4
以上制得的聚合物1-23用来实施下面的实验。出于比较的目的,也测试了下面常规的MDFI:
对比产品A:基于乙烯-乙酸乙烯酯的聚合物混合物;聚合物含量60%(Keroflux 6100,BASF AG)
对比产品B:基于乙烯-乙酸乙烯酯的聚合物;聚合物含量50%(Keroflux 6103,BASF AG)
对比产品C:乙烯三聚物;聚合物含量75%
对比产品D:基于乙烯-乙酸乙烯酯的聚合物混合物;聚合物含量60%
将常规的中间镏分燃料与以上本发明的或常规的冷流改进剂以不同剂量进行添加,并测定添加剂的下限混合温度、CP值(浊点)、PP值(倾点)和粘度以及经添加燃料的CFPP值(冷滤堵塞点)。下限混合温度根据QSAA FKL 103、5.4.2部分(ARAL Research)测定,CP值根据ASTMD 2500测定,添加剂的PP值根据ISO 3016测定,添加剂的粘度根据DIN51512测定,CFPP值根据DIN EN 116测定。
测试实施例1:下限混合温度
通过使用本发明中所用聚合物的50%在Solvent Naphtha heavy中的溶液来调查在中间馏分中的下限混合温度。该下限混合温度对于将未加热的添加剂混入燃料油中或将添加剂混入未加热的燃料油中的那些精炼厂特别重要。当添加剂的下限混合温度较高时,未加热的混合可能导致过滤问题。
所用的中间馏分:柴油燃料,CP=-5℃,CFPP=-9℃,25%正构链烷烃,90-20=70℃。
添加剂的用量:500ppm
表2
添加剂 | 下限混合温度[℃] |
无添加剂 | <10 |
聚合物1 | 10 |
聚合物4 | 10 |
聚合物7 | 10 |
聚合物8 | 10 |
聚合物12 | 10 |
聚合物13 | 10 |
聚合物15 | 10 |
聚合物16 | 10 |
对比产品A | 20 |
对比产品C | 15 |
对比产品D | 35 |
如以上结果所示的,本发明聚合物的50%溶液显示出比常规添加剂溶液明显更低的下限混合温度。
测试实施例2:添加剂的倾点(PP)
通过使用聚合物的50%在Solvent Naphtha heavy中的溶液,根据ISO3016测定添加剂的PP。添加剂的倾点对于在将它们混入燃料油中时的处理具有重要作用。非常低的PP使得即使在低温下混合也能方便地处理添加剂,并节约了添加剂槽的加热成本。
表3
添加剂 | PP[℃] |
聚合物2 | 6 |
聚合物4 | 12 |
聚合物7 | -36 |
聚合物9 | -6 |
聚合物16 | -6 |
聚合物17 | 18 |
聚合物19 | -18 |
聚合物20 | 6 |
对比产品A | 21 |
如以上结果所示的,本发明添加剂的50%溶液具有比常规添加剂的溶液明显更低的倾点。
测试实施例3:粘度
通过使用本发明聚合物的50%在Solvent Naphtha中的溶液,根据DIN51512在50℃下测定粘度。添加剂的粘度对于在低温下将其混合的处理也是重要的。
表4
添加剂 | η[mm2/s] |
聚合物2 | 40 |
聚合物7 | 18 |
聚合物12 | 27 |
聚合物13 | 52 |
聚合物16 | 40 |
聚合物19 | 35 |
对比产品A | 55 |
如以上结果所示的,本发明添加剂的50%溶液具有比常规添加剂溶液明显更低的粘度。
测试实施例4:对中间镏分的冷流性能的改进
实施例a)
所用的中间镏分:LGO,荷兰,CP=1.7℃,CFPP=-1℃,25%正构链烷烃,90-20=70℃。
添加剂的用量:1500ppm
表5
添加剂 | CFPP[℃] |
聚合物2 | -15 |
聚合物3 | -15 |
聚合物6 | -15 |
聚合物13 | -14 |
聚合物16 | -13 |
聚合物17 | -16 |
对比产品A | -7 |
对比产品B | -10 |
对比产品C | -6 |
对比产品D | -10 |
实施例b)
所用的中间镏分:柴油,比利时,CP=-17℃,CFPP=-19℃,19%正构链烷烃,90-20=89℃。
添加剂的用量:300ppm
表6
添加剂 | CFPP[℃] |
聚合物5 | -25 |
聚合物16 | -25 |
对比产品A | -23 |
对比产品B | -23 |
对比产品C | -24 |
对比产品D | -23 |
实施例c)
所用的中间镏分:柴油燃料,日本,CP=-3.6℃,CFPP=-5℃,21%正构链烷烃,90-20=90℃。
添加剂的用量:1500ppm
表7
添加剂 | CFPP[℃] |
聚合物6 | -14 |
聚合物16 | -16 |
比较产物A | -8 |
比较产物B | -6 |
比较产物C | -11 |
比较产物D | -14 |
实施例d)
所用的中间镏分:柴油燃料,德国,CP=-3.3℃,CFPP=-5℃,18%正构链烷烃,90-20=101℃。
添加剂的用量:150ppm
表8
添加剂 | CFPP[℃] |
聚合物3 | -20 |
聚合物12 | -20 |
聚合物13 | -20 |
聚合物14 | -21 |
聚合物17 | -20 |
对比产品A | -16 |
对比产品B | -18 |
对比产品C | -18 |
对比产品D | -18 |
实施例e)
所用的中间镏分:LHO,比利时,CP=0℃,CFPP=-1℃,18%正构链烷烃,90-20=125℃。
添加剂的用量:350ppm
表9
添加剂 | CFPP[℃] |
聚合物2 | -19 |
聚合物3 | -19 |
聚合物6 | -19 |
聚合物16 | -16 |
聚合物17 | -17 |
聚合物20 | -18 |
对比产品A | -13 |
对比产品B | -13 |
对比产品C | -15 |
对比产品D | -13 |
实施例f)
所用的中间镏分:柴油,荷兰,CP=-5℃,CFPP=-9℃。
添加剂的用量:400ppm
表10
添加剂 | CFPP[℃] |
聚合物16 | -21 |
聚合物20 | -21 |
对比产品A | -18 |
对比产品B | -18 |
对比产品C | -19 |
对比产品D | -19 |
实施例g)
所用的中间镏分:柴油,波兰,CP=-12℃,CFPP=-13℃,12%正构链烷烃,90-20=73℃。
添加剂的用量:600ppm
表11
添加剂 | CFPP[℃] |
聚合物2 | -23 |
聚合物15 | -22 |
聚合物16 | -24 |
对比产品A | -18 |
对比产品B | -17 |
对比产品C | -21 |
对比产品D | -20 |
表5-11中的测试结果证实了本发明聚合物作为中间镏分燃料组合物中的冷流改进剂的令人惊讶的良好性能。因此,本发明的添加剂使得首先在较低用量下设定与常规MDFI相当的CFPP值成为可能,或在相同用量下具有改进的CFPP值。
如测试实施例1-3所示的,本发明的聚合物还使得能够进行更好和更方便的处理,因为它们可以在低温下混合,并且具有比常规添加剂低的粘度和低的倾点,从而使得在将它们混入燃料油中之前不必进行加热,或只需小程度地加热。
Claims (19)
1.一种包含共聚的α-烯烃、乙烯基酯和α,β-不饱和羧酸酯的聚合物用作燃料油和润滑剂的添加剂的用途。
2.根据权利要求1的用途,其中所述聚合物包含无规分布共聚的乙烯基酯和α,β-不饱和羧酸酯。
4.根据权利要求3的用途,其中所述单体M1、M2和M3在聚合物中以下面的摩尔比例存在:
M1:从0.60到0.98;
M2:从0.01到0.20;
M3:从0.01到0.20。
5.根据权利要求3或4的用途,其中所述单体M1是乙烯。
6.根据权利要求3-5任一项的用途,其中R2、R3和R4都是H,或R2、R3和R4基中两个都是H,且另一基团是甲基。
7.根据权利要求3-6任一项的用途,其中R5是C1-C9烃基。
8.根据权利要求7的用途,其中R5是正丁基或2-乙基己基。
9.根据权利要求6-8任一项的用途,其中M2是丙烯酸正丁酯或丙烯酸2-乙基己酯。
10.根据权利要求3-9任一项的用途,其中M3是乙酸乙烯酯。
11.根据前述权利要求任一项的用途,其中所述聚合物用作冷流改进剂。
12.一种燃料油组合物,其包含主要重量比例的沸程为120-500℃的中间馏分燃料和较小重量比例的至少一种如权利要求1-11任一项中定义的聚合物。
13.根据权利要求12的燃料油组合物,其中燃料组分包括0-100重量%的生物柴油(来自动物或植物生产中)。
14.根据权利要求12的燃料油组合物,其选自柴油燃料、煤油和燃料油。
15.根据权利要求14的燃料油组合物,其中柴油燃料可通过精炼、煤气化或气体液化获得,或者是这种产品的混合物并任选地与可再生燃料混合。
16.根据权利要求12-15任一项的燃料油组合物,其中混合物的硫含量至多为500ppm。
17.一种润滑剂组合物,其包含主要重量比例的常规润滑剂和较小重量比例的至少一种如权利要求1-10任一项中定义的聚合物。
18.根据前述权利要求任一项的用途或组合物,其中聚合物和其它常规冷流改进剂和/或其它润滑剂和燃料油添加剂组合使用。
19.一种添加剂包装体,其包含至少一种如权利要求1-10任一项定义的聚合物和至少一种其它常规润滑剂或燃料油添加剂。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10356595A DE10356595A1 (de) | 2003-12-04 | 2003-12-04 | Brennstoffölzusammensetzungen mit verbesserten Kaltfließeigenschaften |
DE10356595.7 | 2003-12-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1890274A true CN1890274A (zh) | 2007-01-03 |
CN100516095C CN100516095C (zh) | 2009-07-22 |
Family
ID=34625532
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2004800360815A Expired - Fee Related CN100516095C (zh) | 2003-12-04 | 2004-12-03 | 具有改进冷流性质的燃料油组合物 |
Country Status (12)
Country | Link |
---|---|
US (5) | US20090282732A1 (zh) |
EP (1) | EP1692196B1 (zh) |
JP (1) | JP2007513231A (zh) |
KR (1) | KR101207057B1 (zh) |
CN (1) | CN100516095C (zh) |
AT (1) | ATE404595T1 (zh) |
CA (1) | CA2548008C (zh) |
DE (2) | DE10356595A1 (zh) |
ES (1) | ES2311870T3 (zh) |
PL (1) | PL1692196T3 (zh) |
PT (1) | PT1692196E (zh) |
WO (1) | WO2005054314A2 (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102549120A (zh) * | 2009-07-03 | 2012-07-04 | 道达尔炼油与销售部 | 乙烯/醋酸乙烯酯/不饱和酯三元共聚物作为改善液态烃如中间馏分和燃料的耐低温性能的添加剂 |
CN102985455A (zh) * | 2010-07-06 | 2013-03-20 | 巴斯夫欧洲公司 | 具有高化学均匀性的共聚物及其用于改进燃料油的低温流动性能的用途 |
CN115677892A (zh) * | 2022-09-29 | 2023-02-03 | 云南正邦科技有限公司 | 一种乙烯-乙酸乙烯酯-丙烯酸类三元共聚物及制备方法和应用 |
Families Citing this family (81)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2602220C (en) | 2005-03-29 | 2013-12-17 | Arizona Chemical Company | Compostions containing fatty acids and/or derivatives thereof and a low temperature stabilizer |
DE102006016588A1 (de) * | 2006-04-06 | 2007-10-18 | Rohmax Additives Gmbh | Kraftstoffzusammensetzungen umfassend nachwachsende Rohstoffe |
EP1923454A1 (de) | 2006-11-17 | 2008-05-21 | Basf Se | Kaltfliessverbesserer |
EP2129752A1 (de) * | 2007-03-22 | 2009-12-09 | Basf Se | Mischung aus kaltfliessverbesserern und aminen |
FR2925909B1 (fr) * | 2007-12-26 | 2010-09-17 | Total France | Additifs bifonctionnels pour hydrocarbures liquides obtenus par greffage a partir de copolymeres d'ethylene et/ou de propylene et d'esters vinyliques |
FR2925916B1 (fr) * | 2007-12-28 | 2010-11-12 | Total France | Terpolymere ethylene/acetate de vinyle/esters insatures comme additif ameliorant la tenue a froid des hydrocarbures liquides comme les distillats moyens et les carburants ou combustibles |
DE102010001408A1 (de) | 2009-02-06 | 2010-08-12 | Basf Se | Verwendung von Ketonen als Kraftstoffzusatz zur Verringerung des Kraftstoffverbrauches von Dieselmotoren |
DE102010039039A1 (de) | 2009-08-24 | 2011-03-03 | Basf Se | Verwendung von organischen Verbindungen als Kraftstoffzusatz zur Verringerung des Kraftstoffverbrauchs von Dieselmotoren |
MX2009010135A (es) | 2009-09-22 | 2011-03-22 | Inst Mexicano Del Petroleo Star | Formulacion de polimeros aleatorios para mejorar flujo de crudos del petroleo. |
ATE547472T1 (de) | 2009-09-25 | 2012-03-15 | Evonik Rohmax Additives Gmbh | Zusammensetzung zur verbesserung der kaltflusseigenschaften von brennstoffölen |
KR20130060205A (ko) | 2010-04-27 | 2013-06-07 | 바스프 에스이 | 4급화 삼원중합체 |
US8790426B2 (en) | 2010-04-27 | 2014-07-29 | Basf Se | Quaternized terpolymer |
MX2012014797A (es) | 2010-06-25 | 2013-04-03 | Basf Se | Copolimero cuaternizado. |
US8911516B2 (en) | 2010-06-25 | 2014-12-16 | Basf Se | Quaternized copolymer |
WO2012004300A1 (de) | 2010-07-06 | 2012-01-12 | Basf Se | Säurefreie quaternisierte stickstoffverbindungen und deren verwendung als additive in kraft- und schmierstoffen |
FR2969620B1 (fr) | 2010-12-23 | 2013-01-11 | Total Raffinage Marketing | Resines alkylphenol-aldehyde modifiees, leur utilisation comme additifs ameliorant les proprietes a froid de carburants et combustibles hydrocarbones liquides |
EP2514774B2 (en) † | 2011-04-21 | 2019-08-14 | Infineum International Limited | Improvements in polymers |
EP2540808A1 (de) | 2011-06-28 | 2013-01-02 | Basf Se | Quaternisierte Stickstoffverbindungen und deren Verwendung als Additive in Kraft- und Schmierstoffen |
US20130133243A1 (en) | 2011-06-28 | 2013-05-30 | Basf Se | Quaternized nitrogen compounds and use thereof as additives in fuels and lubricants |
EP2589647A1 (de) | 2011-11-04 | 2013-05-08 | Basf Se | Quaternisierte Polyetheramine und deren Verwendung als Additive in Kraft- und Schmierstoffen |
EP2604674A1 (de) | 2011-12-12 | 2013-06-19 | Basf Se | Verwendung quaternisierter Alkylamine als Additive in Kraft- und Schmierstoffen |
ES2711361T3 (es) | 2012-02-10 | 2019-05-03 | Basf Se | Sales de imidazolio como aditivos para carburantes y combustibles |
US9062266B2 (en) | 2012-02-10 | 2015-06-23 | Basf Se | Imidazolium salts as additives for fuels |
CA2865869A1 (en) | 2012-03-07 | 2013-09-12 | Basf Se | Use of substituted ureas or urethanes for improvement of the use properties of mineral and synthetic nonaqueous industrial fluids |
WO2013131837A1 (de) | 2012-03-07 | 2013-09-12 | Basf Se | VERWENDUNG VON SUBSTITUIERTEN HARNSTOFFEN ODER URETHANEN ZUR WEITEREN VERBESSERUNG DER KALTFLIEßEIGENSCHAFTEN VON MINERALÖLEN UND ROHÖLEN |
US9458401B2 (en) | 2012-03-07 | 2016-10-04 | Basf Se | Use of substituted ureas or urethanes for improvement of the use properties of mineral and synthetic nonaqueous industrial fluids |
EP2664663A1 (de) | 2012-05-15 | 2013-11-20 | SSL Energizer Technologies AG | Verfahren zur Herstellung eines Treibstoffadditivs |
FR2991992B1 (fr) | 2012-06-19 | 2015-07-03 | Total Raffinage Marketing | Compositions d'additifs et leur utilisation pour ameliorer les proprietes a froid de carburants et combustibles |
AU2013336727A1 (en) | 2012-10-23 | 2015-05-14 | Basf Se | Quaternized ammonium salts of hydrocarbyl epoxides and use thereof as additives in fuels and lubricants |
US11440815B2 (en) | 2013-02-22 | 2022-09-13 | Anschutz Exploration Corporation | Method and system for removing hydrogen sulfide from sour oil and sour water |
US9708196B2 (en) | 2013-02-22 | 2017-07-18 | Anschutz Exploration Corporation | Method and system for removing hydrogen sulfide from sour oil and sour water |
US9364773B2 (en) | 2013-02-22 | 2016-06-14 | Anschutz Exploration Corporation | Method and system for removing hydrogen sulfide from sour oil and sour water |
CA2843041C (en) | 2013-02-22 | 2017-06-13 | Anschutz Exploration Corporation | Method and system for removing hydrogen sulfide from sour oil and sour water |
FR3005061B1 (fr) | 2013-04-25 | 2016-05-06 | Total Raffinage Marketing | Additif pour ameliorer la stabilite a l'oxydation et/ou au stockage de carburants ou combustibles hydrocarbones liquides |
EP2811007A1 (de) | 2013-06-07 | 2014-12-10 | Basf Se | Verwendung mit Alkylenoxid und Hydrocarbyl-substituierter Polycarbonsäure quaternisierter Alkylamine als Additive in Kraft- und Schmierstoffen |
AU2014276831B2 (en) | 2013-06-07 | 2017-06-08 | Basf Se | Use of nitrogen compounds quaternised with alkylene oxide and hydrocarbyl-substituted polycarboxylic acid as additives in fuels and lubricants |
KR20160055276A (ko) | 2013-09-20 | 2016-05-17 | 바스프 에스이 | 연료 및 윤활제 첨가제로서의 사차화된 질소 화합물의 특정 유도체의 용도 |
CN109486539B (zh) | 2014-01-29 | 2020-12-04 | 巴斯夫欧洲公司 | 用于燃料和润滑剂的多羧酸基添加剂 |
CA2938220A1 (en) | 2014-01-29 | 2015-08-06 | Basf Se | Corrosion inhibitors for fuels and lubricants |
AR100387A1 (es) | 2014-02-18 | 2016-10-05 | Basf Se | Copolímeros que comprenden etileno, ésteres de vinilo y ésteres de ácido (met)acrílico, sus formulaciones y usos como depresor del punto de fluidez, inhibidor de cera y potenciador de flujo para petróleos crudos |
BR112016028032A2 (pt) | 2014-05-30 | 2017-08-22 | Lubrizol Corp | Sais de amônio quaternário acoplados |
MX2016015749A (es) | 2014-05-30 | 2017-04-10 | Lubrizol Corp | Imida de bajo peso molecular que contiene sales de amonio cuaternario. |
CN111253994B (zh) | 2014-05-30 | 2022-10-04 | 路博润公司 | 低分子量含酰胺/酯季铵盐 |
BR112016028067A2 (pt) | 2014-05-30 | 2017-08-22 | Lubrizol Corp | Amida/éster de alto peso molecular contendo sais de amônio quaternário |
SG11201609885XA (en) | 2014-05-30 | 2016-12-29 | Lubrizol Corp | Branched amine containing quaternary ammonium salts |
SG11201609882UA (en) | 2014-05-30 | 2016-12-29 | Lubrizol Corp | Epoxide quaternized quaternary ammonium salts |
EP3524663A1 (en) | 2014-05-30 | 2019-08-14 | The Lubrizol Corporation | Imidazole containing quaternary ammonium salts |
SG11201609725XA (en) | 2014-05-30 | 2016-12-29 | Lubrizol Corp | High molecular weight imide containing quaternary ammonium salts |
JP2016017170A (ja) * | 2014-07-11 | 2016-02-01 | 東亞合成株式会社 | 潤滑油用添加剤及び潤滑油組成物 |
WO2016083090A1 (de) | 2014-11-25 | 2016-06-02 | Basf Se | Korrosionsinhibitoren für kraft- und schmierstoffe |
FR3034778B1 (fr) | 2015-04-10 | 2017-04-28 | Total Marketing Services | Additif dispersant des asphaltenes et ses utilisations |
US11085001B2 (en) | 2015-07-16 | 2021-08-10 | Basf Se | Copolymers as additives for fuels and lubricants |
WO2017016909A1 (de) | 2015-07-24 | 2017-02-02 | Basf Se | Korrosionsinhibitoren für kraft- und schmierstoffe |
EP3144059A1 (en) | 2015-09-16 | 2017-03-22 | Total Marketing Services | Method for preparing microcapsules by double emulsion |
BR112018011140A2 (pt) | 2015-12-02 | 2018-11-21 | The Lubrizol Corporation | sais de amônio quaternário que contêm imida com peso molecular ultrabaixo que têm caudas de hidrocarboneto curtas |
US20180355267A1 (en) | 2015-12-02 | 2018-12-13 | The Lubrizol Corporation | Ultra-low molecular weight amide/ester containing quaternary ammonium salts having short hydrocarbon tails |
US10844308B2 (en) | 2016-07-05 | 2020-11-24 | Basf Se | Corrosion inhibitors for fuels and lubricants |
ES2896694T3 (es) | 2016-07-05 | 2022-02-25 | Basf Se | Uso de inhibidores de la corrosión para combustibles y lubricantes |
WO2018007486A1 (de) | 2016-07-07 | 2018-01-11 | Basf Se | Polymere als additive für kraft und schmierstoffe |
WO2018007445A1 (de) | 2016-07-07 | 2018-01-11 | Basf Se | Korrosionsinhibitoren für kraft- und schmierstoffe |
US20190249099A1 (en) | 2016-07-07 | 2019-08-15 | Basf Se | Copolymers as additives for fuels and lubricants |
AU2017330331B2 (en) | 2016-09-21 | 2022-04-07 | The Lubrizol Corporation | Polyacrylate antifoam components for use in diesel fuels |
EP3555244B1 (de) | 2016-12-15 | 2023-05-31 | Basf Se | Polymere als dieselkraftstoffadditive für direkteinspritzende dieselmotoren |
EP3555242B1 (de) | 2016-12-19 | 2020-11-25 | Basf Se | Additive zur verbesserung der thermischen stabilität von kraftstoffen |
WO2018188986A1 (de) | 2017-04-13 | 2018-10-18 | Basf Se | Polymere als additive für kraft und schmierstoffe |
BR112020005563B1 (pt) | 2017-09-21 | 2023-11-21 | The Lubrizol Corporation | Composição antiespuma de poliacrilato para uso em combustíveis, método, pacote de aditivo de combustível e uso dos mesmos |
US11639479B2 (en) | 2018-03-21 | 2023-05-02 | The Lubrizol Corporation | Polyacrylamide antifoam components for use in diesel fuels |
WO2020260062A1 (en) | 2019-06-26 | 2020-12-30 | Basf Se | New additive packages for gasoline fuels |
BR112022011985A2 (pt) | 2019-12-19 | 2022-08-30 | Lubrizol Corp | Composição de aditivo antissedimentação de cera para uso em combustíveis diesel |
EP3913035A1 (en) | 2020-05-20 | 2021-11-24 | Basf Se | Novel compositions for reducing crystallization of paraffin crystals in fuels |
PL3940043T3 (pl) | 2020-07-14 | 2024-02-19 | Basf Se | Inhibitory korozji do paliw silnikowych i smarów |
US11542454B2 (en) | 2020-07-31 | 2023-01-03 | Iowa State University Research Foundation, Inc. | Base oil or lubricant additive |
FR3118056B1 (fr) | 2020-12-22 | 2024-01-05 | Total Marketing Services | Composition d’additifs comprenant un copolymere et une resine |
CA3233684A1 (en) | 2021-10-04 | 2023-04-13 | Innospec Fuel Specialties Llc | Improvements in fuels |
EP4166633A1 (en) | 2021-10-15 | 2023-04-19 | Innospec Fuel Specialties LLC | Improvements in fuels |
CA3237233A1 (en) | 2021-11-16 | 2023-05-25 | Richard HEDIGER | Method for producing of a fuel additive |
WO2023233152A1 (en) | 2022-06-01 | 2023-12-07 | Innospec Fuel Specialties Llc | Improvements in fuels |
WO2024030591A1 (en) | 2022-08-05 | 2024-02-08 | The Lubrizol Corporation | Processes for producing reaction products including quaternary ammonium salts |
WO2024037904A1 (de) | 2022-08-16 | 2024-02-22 | Basf Se | Zusammensetzung zur verminderung der kristallisation von paraffinkristallen in kraftstoffen |
WO2024115211A1 (en) | 2022-11-30 | 2024-06-06 | Basf Se | Homo- and copolymers of vinyl ethers for reducing crystallization of paraffin crystals in fuels |
EP4382588A1 (de) | 2022-12-06 | 2024-06-12 | Basf Se | Additive zur verbesserung der thermischen stabilität von kraftstoffen |
Family Cites Families (60)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE254956C (zh) | 1900-01-01 | |||
US3038479A (en) | 1957-12-16 | 1962-06-12 | Colli Eduard | Hairpins |
US3627838A (en) | 1964-12-11 | 1971-12-14 | Exxon Research Engineering Co | Process for manufacturing potent pour depressants |
US3304261A (en) * | 1966-01-24 | 1967-02-14 | Exxon Research Engineering Co | Mineral lubricating oil compositions containing terpolymer viscosity index improvers |
US3467597A (en) | 1966-11-22 | 1969-09-16 | Exxon Research Engineering Co | Grafted terpolymers,their process of production,and use as additives for lubricants and fuels |
US3642459A (en) | 1968-04-01 | 1972-02-15 | Exxon Research Engineering Co | Copolymers of ethylene with unsaturated esters and oil compositions containing said copolymers |
DE1914756C3 (de) | 1968-04-01 | 1985-05-15 | Exxon Research and Engineering Co., Linden, N.J. | Verwendung von Ethylen-Vinylacetat- Mischpolymerisaten für Erdöl-Destillate |
DE2102469C2 (de) | 1971-01-20 | 1989-06-29 | Basf Ag, 6700 Ludwigshafen | Verwendung von Äthylencopolymerisaten als Zusatz zu Erdöl und Erdölfraktionen |
CA1000501A (en) | 1972-06-21 | 1976-11-30 | Levi C. Parker | Low pour point fuel compositions |
US3961961A (en) | 1972-11-20 | 1976-06-08 | Minnesota Mining And Manufacturing Company | Positive or negative developable photosensitive composition |
GB1499568A (en) | 1974-04-17 | 1978-02-01 | Exxon Research Engineering Co | Preparation of copolymers of ethylene and ethylenically unsaturated monomers and distillate oil containing copolymers so produced |
US4155719A (en) * | 1977-11-23 | 1979-05-22 | Texaco Inc. | Low pour residual fuel compositions |
US4211534A (en) * | 1978-05-25 | 1980-07-08 | Exxon Research & Engineering Co. | Combination of ethylene polymer, polymer having alkyl side chains, and nitrogen containing compound to improve cold flow properties of distillate fuel oils |
EP0007590B1 (de) | 1978-07-26 | 1981-02-18 | BASF Aktiengesellschaft | Mitteldestillate des Erdöls, die als Dieseltreibstoffe oder leichtes Heizöl geeignet sind, mit verbesserter Filtrierbarkeit |
JPS5661488A (en) * | 1979-10-25 | 1981-05-26 | Nippon Synthetic Chem Ind Co Ltd:The | Hydrocarbon oil composition |
US4464182A (en) | 1981-03-31 | 1984-08-07 | Exxon Research & Engineering Co. | Glycol ester flow improver additive for distillate fuels |
JPS5823885A (ja) | 1981-08-03 | 1983-02-12 | Sumitomo Chem Co Ltd | 燃料油の低温流動性改良法 |
JPS5840391A (ja) | 1981-09-03 | 1983-03-09 | Sumitomo Chem Co Ltd | 燃料油の低温流動性改良方法 |
DE3141507A1 (de) | 1981-10-20 | 1983-04-28 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von ethylenpolymerisaten in einem zweizonen-rohrreaktor bei druecken oberhalb 500 bar |
JPS58138791A (ja) | 1982-02-10 | 1983-08-17 | Nippon Oil & Fats Co Ltd | 燃料油用流動性向上剤 |
JPS59108093A (ja) * | 1982-12-10 | 1984-06-22 | Nippon Synthetic Chem Ind Co Ltd:The | 燃料組成物 |
JPS6270488A (ja) | 1985-09-24 | 1987-03-31 | Mitsubishi Petrochem Co Ltd | 燃料油添加剤および流動性の改善された燃料油 |
DE3613247C2 (de) | 1986-04-19 | 1995-04-27 | Roehm Gmbh | Konzentrierte Emulsionen aus Ethylen-Vinylacetat-Copolymeren, Verfahren zu deren Herstellung und deren Verwendung als Stockpunktverbesserer |
IN184481B (zh) | 1986-09-24 | 2000-08-26 | Exxon Chemical Patents Inc | |
DD254956A1 (de) | 1986-12-17 | 1988-03-16 | Leuna Werke Veb | Verfahren zur verbesserung des kaelteverhaltens von erdoelmitteldestillaten |
FR2613371B1 (fr) | 1987-04-01 | 1989-07-07 | Inst Francais Du Petrole | Copolymeres azotes, leur preparation et leur utilisation comme additifs pour ameliorer les proprietes d'ecoulement des distillats moyens d'hydrocarbures |
DE3916366A1 (de) | 1989-05-19 | 1990-11-22 | Basf Ag | Neue umsetzungsprodukte von aminoalkylenpolycarbonsaeuren mit sekundaeren aminen und erdoelmitteldestillatzusammensetzungen, die diese enthalten |
GB9213870D0 (en) | 1992-06-30 | 1992-08-12 | Exxon Chemical Patents Inc | Oil additives and compositions |
GB9213904D0 (en) | 1992-06-30 | 1992-08-12 | Exxon Chemical Patents Inc | Oil additives and compositions |
GB9315205D0 (en) | 1993-07-22 | 1993-09-08 | Exxon Chemical Patents Inc | Additives and fuel compositions |
GB9417670D0 (en) | 1994-09-02 | 1994-10-19 | Exxon Chemical Patents Inc | Oil additives, compositions and polymers for use therein |
GB9424565D0 (en) | 1994-12-06 | 1995-01-25 | Exxon Chemical Patents Inc | Fuel oil compositions |
AR001122A1 (es) | 1995-03-06 | 1997-09-24 | Akzo Nobel Nv | Procedimiento de polímerizacion que utiliza una composición de peróxidos (co)polímero funcionalizadoobtenido por el proceso y uso de una composición de peróxidos |
GB9508644D0 (en) | 1995-04-28 | 1995-06-14 | Exxon Chemical Patents Inc | Fuel compositions |
US5882364A (en) * | 1995-07-14 | 1999-03-16 | Exxon Chemical Patents Inc. | Additives and fuel oil compositions |
JP3524237B2 (ja) | 1995-09-27 | 2004-05-10 | ソニー株式会社 | 電気自動車のバッテリ構造 |
DE19622052A1 (de) | 1996-05-31 | 1997-12-04 | Basf Ag | Paraffindispergatoren für Erdölmitteldestillate |
GB9725582D0 (en) * | 1997-12-03 | 1998-02-04 | Exxon Chemical Patents Inc | Fuel oil additives and compositions |
DE19754555A1 (de) | 1997-12-09 | 1999-06-24 | Clariant Gmbh | Verfahren zur Herstellung von Ethylen-Mischpolymerisaten und deren Verwendung als Zusatz zu Mineralöl und Mineralöldestillaten |
DE19757830C2 (de) | 1997-12-24 | 2003-06-18 | Clariant Gmbh | Brennstofföle mit verbesserter Schmierwirkung |
DE19848621A1 (de) | 1998-10-21 | 2000-04-27 | Basf Ag | Paraffindispergatoren mit Lubricity-Wirkung für Erdölmitteldestillate |
GB9827366D0 (en) | 1998-12-11 | 1999-02-03 | Exxon Chemical Patents Inc | Macromolecular materials |
DE10012946B4 (de) * | 2000-03-16 | 2006-02-02 | Clariant Gmbh | Verwendung von öllöslichen Amphiphilen als Lösemittel für hydroxyfunktionelle Copolymere |
JP4196521B2 (ja) | 2000-05-19 | 2008-12-17 | 新神戸電機株式会社 | 電気自動車用バッテリ構造及び電池モジュール |
WO2002090470A1 (fr) | 2001-05-08 | 2002-11-14 | Sanyo Chemical Industries, Ltd. | Agent fluidifiant et composition de mazout |
US7261974B2 (en) | 2001-11-01 | 2007-08-28 | Honda Giken Kogyo Kabushiki Kaisha | Battery-driven power source apparatus |
CN1137972C (zh) | 2001-11-17 | 2004-02-11 | 中国石油化工集团公司 | 一种柴油低温流动添加剂 |
KR100930474B1 (ko) | 2005-12-08 | 2009-12-09 | 주식회사 엘지화학 | 전지모듈 제조용 조립식 스페이서 |
CN101820053B (zh) | 2005-12-27 | 2012-12-19 | 株式会社Lg化学 | 电池组间隔件 |
KR100853620B1 (ko) | 2006-01-16 | 2008-08-25 | 주식회사 엘지화학 | 전지모듈 제조용 스페이서 |
KR101256063B1 (ko) | 2006-06-08 | 2013-04-18 | 삼성에스디아이 주식회사 | 전지 모듈 |
JP5057720B2 (ja) | 2006-08-10 | 2012-10-24 | 三洋電機株式会社 | パック電池 |
JP5004534B2 (ja) | 2006-08-21 | 2012-08-22 | 三洋電機株式会社 | パック電池 |
KR100862436B1 (ko) | 2006-11-29 | 2008-10-08 | 현대자동차주식회사 | 배터리 모듈 냉각용 지지장치 |
US8252441B2 (en) | 2007-08-31 | 2012-08-28 | Micro Power Electronics, Inc. | Spacers for fixing battery cells within a battery package casing and associated systems and methods |
ATE495555T1 (de) | 2007-09-21 | 2011-01-15 | Bosch Gmbh Robert | Akkupack |
JP4960839B2 (ja) | 2007-11-12 | 2012-06-27 | 本田技研工業株式会社 | 車両用バッテリ冷却装置 |
US8455133B2 (en) | 2008-01-29 | 2013-06-04 | Cobasys, Llc | Battery pack |
FR2947558B1 (fr) * | 2009-07-03 | 2011-08-19 | Total Raffinage Marketing | Terpolymere et ethylene/acetate de vinyle/esters insatures comme additif ameliorant la tenue a froid des hydrocarbures liquides comme les distillats moyens et les carburants ou combustibles |
KR101097258B1 (ko) | 2009-12-04 | 2011-12-21 | 삼성에스디아이 주식회사 | 배터리 팩 |
-
2003
- 2003-12-04 DE DE10356595A patent/DE10356595A1/de not_active Withdrawn
-
2004
- 2004-12-03 DE DE502004007860T patent/DE502004007860D1/de active Active
- 2004-12-03 WO PCT/EP2004/013781 patent/WO2005054314A2/de active IP Right Grant
- 2004-12-03 CN CNB2004800360815A patent/CN100516095C/zh not_active Expired - Fee Related
- 2004-12-03 KR KR1020067013457A patent/KR101207057B1/ko active IP Right Grant
- 2004-12-03 EP EP04803502A patent/EP1692196B1/de not_active Revoked
- 2004-12-03 AT AT04803502T patent/ATE404595T1/de active
- 2004-12-03 JP JP2006541910A patent/JP2007513231A/ja active Pending
- 2004-12-03 PL PL04803502T patent/PL1692196T3/pl unknown
- 2004-12-03 ES ES04803502T patent/ES2311870T3/es active Active
- 2004-12-03 PT PT04803502T patent/PT1692196E/pt unknown
- 2004-12-03 CA CA2548008A patent/CA2548008C/en active Active
-
2009
- 2009-06-26 US US12/493,104 patent/US20090282732A1/en not_active Abandoned
-
2011
- 2011-01-21 US US13/011,614 patent/US8642521B2/en active Active
-
2013
- 2013-12-20 US US14/136,401 patent/US9605227B2/en active Active
-
2017
- 2017-02-06 US US15/425,427 patent/US10047314B2/en active Active
-
2018
- 2018-07-26 US US16/046,034 patent/US10526558B2/en active Active
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102549120A (zh) * | 2009-07-03 | 2012-07-04 | 道达尔炼油与销售部 | 乙烯/醋酸乙烯酯/不饱和酯三元共聚物作为改善液态烃如中间馏分和燃料的耐低温性能的添加剂 |
TWI496883B (zh) * | 2009-07-03 | 2015-08-21 | Total Raffinage Marketing | 乙烯/乙酸乙烯酯/不飽和酯三元聚合物作為改善液態烴如中間餾出物和燃料或可燃燒材料之耐冷性的添加劑 |
CN102985455A (zh) * | 2010-07-06 | 2013-03-20 | 巴斯夫欧洲公司 | 具有高化学均匀性的共聚物及其用于改进燃料油的低温流动性能的用途 |
CN102985455B (zh) * | 2010-07-06 | 2016-01-20 | 巴斯夫欧洲公司 | 具有高化学均匀性的共聚物及其用于改进燃料油的低温流动性能的用途 |
CN115677892A (zh) * | 2022-09-29 | 2023-02-03 | 云南正邦科技有限公司 | 一种乙烯-乙酸乙烯酯-丙烯酸类三元共聚物及制备方法和应用 |
CN115677892B (zh) * | 2022-09-29 | 2023-08-29 | 云南正邦科技有限公司 | 一种乙烯-乙酸乙烯酯-丙烯酸类三元共聚物及制备方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
ES2311870T3 (es) | 2009-02-16 |
EP1692196A2 (de) | 2006-08-23 |
US20110118159A1 (en) | 2011-05-19 |
PL1692196T3 (pl) | 2009-01-30 |
US20090282732A1 (en) | 2009-11-19 |
US20170145335A1 (en) | 2017-05-25 |
US10047314B2 (en) | 2018-08-14 |
US20180334631A1 (en) | 2018-11-22 |
KR20070003814A (ko) | 2007-01-05 |
US20140107005A1 (en) | 2014-04-17 |
US8642521B2 (en) | 2014-02-04 |
DE10356595A1 (de) | 2005-06-30 |
CA2548008C (en) | 2013-05-21 |
US10526558B2 (en) | 2020-01-07 |
EP1692196B1 (de) | 2008-08-13 |
PT1692196E (pt) | 2008-11-03 |
WO2005054314A2 (de) | 2005-06-16 |
DE502004007860D1 (de) | 2008-09-25 |
KR101207057B1 (ko) | 2012-11-30 |
WO2005054314A3 (de) | 2005-09-01 |
CA2548008A1 (en) | 2005-06-16 |
CN100516095C (zh) | 2009-07-22 |
JP2007513231A (ja) | 2007-05-24 |
ATE404595T1 (de) | 2008-08-15 |
US9605227B2 (en) | 2017-03-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1890274A (zh) | 具有改进冷流性质的燃料油组合物 | |
CN106133120B (zh) | 用于燃料和润滑油的腐蚀抑制剂 | |
CN1048520C (zh) | 燃料油组合物 | |
US8338344B2 (en) | Cold flow improver | |
CN107001535B (zh) | 共聚物及其用于降低燃料中的链烷烃晶体结晶的用途 | |
EA019963B1 (ru) | Применение полученных прививкой сополимеров этилена и/или пропилена и виниловых эфиров в качестве бифункциональной добавки в жидких углеводородах для улучшения холодостойкости и смазочных свойств | |
US7476264B2 (en) | Cold flow improvers for fuel oils of vegetable or animal origin | |
JP2009541507A (ja) | 燃料用のパラフィン分散剤としての、極性油溶性窒素化合物と酸アミドからの混合物 | |
CN1025045C (zh) | 流动性改进剂和浊点降低剂 | |
HUE028480T2 (en) | Refined Cold Fluid Fuel Containing Intermediate Spirits and Vegetable or Animal Oils | |
CN1749369A (zh) | 燃油的改善 | |
EA019894B1 (ru) | Применение соединений для снижения температуры фильтруемости углеводородных дистиллятов | |
JP2007308702A (ja) | 燃料油の組成 | |
EA023072B1 (ru) | Композиции полиалкил(мет)акрилатов, свободные от серосодержащих соединений, металлических и галогенированных соединений, с низкой долей остаточных мономеров, способ их получения и их применение | |
JP2008536984A (ja) | 改善された低温特性を有するタービン燃料組成物 | |
CN1795259A (zh) | 具有改进的低温流动性能的燃料组合物 | |
US20070094920A1 (en) | Fuel oil compositions with improved cold flow properties | |
CN1688680A (zh) | 稳定的聚合物分散体和制备方法 | |
JP2018514636A (ja) | 燃料組成物 | |
CN1038254C (zh) | 添加剂组合物及其应用及含它们的燃料油组合物 | |
CN100345947C (zh) | 烯键式不饱和酯的均聚物用于改善冷流改进剂的效用的用途 | |
CN1083857A (zh) | 添加剂及燃料组合物 | |
CN1255938A (zh) | 改进的油组合物 | |
KR20130124293A (ko) | 고 화학적 균질성을 갖는 공중합체 및 연료유의 저온 유동 특성을 향상시키기 위한 이의 용도 | |
CN1024015C (zh) | 改进了冷流性的中间馏分组合物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20090722 |
|
CF01 | Termination of patent right due to non-payment of annual fee |