JPS6249920B2 - - Google Patents
Info
- Publication number
- JPS6249920B2 JPS6249920B2 JP57053630A JP5363082A JPS6249920B2 JP S6249920 B2 JPS6249920 B2 JP S6249920B2 JP 57053630 A JP57053630 A JP 57053630A JP 5363082 A JP5363082 A JP 5363082A JP S6249920 B2 JPS6249920 B2 JP S6249920B2
- Authority
- JP
- Japan
- Prior art keywords
- polyoxyalkylene
- ester
- esters
- weight
- fuel
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 claims description 97
- 239000000654 additive Substances 0.000 claims description 64
- 239000000203 mixture Substances 0.000 claims description 49
- 238000009835 boiling Methods 0.000 claims description 46
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 35
- 230000000996 additive effect Effects 0.000 claims description 32
- -1 amine salt Chemical class 0.000 claims description 27
- 150000002170 ethers Chemical class 0.000 claims description 27
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000013078 crystal Substances 0.000 claims description 11
- 239000010771 distillate fuel oil Substances 0.000 claims description 11
- 239000003966 growth inhibitor Substances 0.000 claims description 11
- 150000001408 amides Chemical class 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 8
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 229920001038 ethylene copolymer Polymers 0.000 claims description 4
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 239000000446 fuel Substances 0.000 description 84
- 229920001223 polyethylene glycol Polymers 0.000 description 48
- 239000002202 Polyethylene glycol Substances 0.000 description 47
- 238000012360 testing method Methods 0.000 description 37
- 239000001993 wax Substances 0.000 description 25
- 239000003921 oil Substances 0.000 description 21
- 229920001451 polypropylene glycol Polymers 0.000 description 21
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 19
- 239000005977 Ethylene Substances 0.000 description 19
- 150000001412 amines Chemical class 0.000 description 17
- 229920001577 copolymer Polymers 0.000 description 16
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 15
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 15
- 239000000178 monomer Substances 0.000 description 11
- 235000021357 Behenic acid Nutrition 0.000 description 8
- 229940116226 behenic acid Drugs 0.000 description 8
- 230000000994 depressogenic effect Effects 0.000 description 8
- 239000005038 ethylene vinyl acetate Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 7
- 150000001735 carboxylic acids Chemical class 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 239000010687 lubricating oil Substances 0.000 description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 7
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 239000003760 tallow Substances 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 229940116224 behenate Drugs 0.000 description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-M behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC([O-])=O UKMSUNONTOPOIO-UHFFFAOYSA-M 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004435 Oxo alcohol Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 235000015278 beef Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 2
- 229920002565 Polyethylene Glycol 400 Polymers 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
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 239000002667 nucleating agent Substances 0.000 description 2
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920001522 polyglycol ester Polymers 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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
- FWUIHQFQLSWYED-ONEGZZNKSA-N (e)-4-oxo-4-propan-2-yloxybut-2-enoic acid Chemical compound CC(C)OC(=O)\C=C\C(O)=O FWUIHQFQLSWYED-ONEGZZNKSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- IJCWFDPJFXGQBN-UHFFFAOYSA-N 2-[4-Hydroxy-3-(octadecanoyloxy)oxolan-2-yl]-2-(octadecanoyloxy)ethyl octadecanoate Polymers CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)C1OCC(O)C1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-UHFFFAOYSA-N 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
- GXXNMQBOGJLFAY-UHFFFAOYSA-N 2-octadecoxycarbonylbenzoic acid Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(O)=O GXXNMQBOGJLFAY-UHFFFAOYSA-N 0.000 description 1
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical class OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- IJCWFDPJFXGQBN-RYNSOKOISA-N [(2R)-2-[(2R,3R,4S)-4-hydroxy-3-octadecanoyloxyoxolan-2-yl]-2-octadecanoyloxyethyl] octadecanoate Polymers CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-RYNSOKOISA-N 0.000 description 1
- IJCWFDPJFXGQBN-JYVCTSCWSA-N [2-[(2R,3R)-4-hydroxy-3-octadecanoyloxyoxolan-2-yl]-2-octadecanoyloxyethyl] octadecanoate Polymers CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OCC(O)[C@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-JYVCTSCWSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 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
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 244000240602 cacao Species 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- OVHKECRARPYFQS-UHFFFAOYSA-N cyclohex-2-ene-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC=C1 OVHKECRARPYFQS-UHFFFAOYSA-N 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- YZFOGXKZTWZVFN-UHFFFAOYSA-N cyclopentane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1 YZFOGXKZTWZVFN-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000004420 diamide group Chemical group 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- HEJZJSIRBLOWPD-WCWDXBQESA-N didodecyl (e)-but-2-enedioate Chemical compound CCCCCCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCCCCCC HEJZJSIRBLOWPD-WCWDXBQESA-N 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- FNMTVMWFISHPEV-WAYWQWQTSA-N dipropan-2-yl (z)-but-2-enedioate Chemical compound CC(C)OC(=O)\C=C/C(=O)OC(C)C FNMTVMWFISHPEV-WAYWQWQTSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- WNMORWGTPVWAIB-UHFFFAOYSA-N ethenyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC=C WNMORWGTPVWAIB-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- UJRIYYLGNDXVTA-UHFFFAOYSA-N ethenyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC=C UJRIYYLGNDXVTA-UHFFFAOYSA-N 0.000 description 1
- ZQZUENMXBZVXIZ-UHFFFAOYSA-N ethenyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC=C ZQZUENMXBZVXIZ-UHFFFAOYSA-N 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical class C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- IJCWFDPJFXGQBN-BIFNRIDTSA-N sorbitan tristearate Polymers CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@@H](O)[C@@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-BIFNRIDTSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- ASLXNOZOXWPTNG-UHFFFAOYSA-N tricosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCN ASLXNOZOXWPTNG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Landscapes
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8110081 | 1981-03-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57177092A JPS57177092A (en) | 1982-10-30 |
| JPS6249920B2 true JPS6249920B2 (ru) | 1987-10-21 |
Family
ID=10520806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5363082A Granted JPS57177092A (en) | 1981-03-31 | 1982-03-31 | Glycol ester flow improving additive for distilled fuel |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS57177092A (ru) |
| CS (1) | CS276707B6 (ru) |
| HU (1) | HU202267B (ru) |
| RU (1) | RU2014347C1 (ru) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59232176A (ja) * | 1983-06-16 | 1984-12-26 | Nippon Oil Co Ltd | デイ−ゼルエンジン用燃料組成物 |
| JPS6028493A (ja) * | 1983-07-25 | 1985-02-13 | Sanyo Chem Ind Ltd | 原油の流動性改良添加剤 |
| JPS60127392A (ja) * | 1983-12-12 | 1985-07-08 | Sanyo Chem Ind Ltd | 燃料油用流動性改良添加剤 |
| JPS60130687A (ja) * | 1983-12-16 | 1985-07-12 | Sanyo Chem Ind Ltd | 燃料油用流動性改良添加剤 |
| GB8428880D0 (en) * | 1984-11-15 | 1984-12-27 | Exxon Research Engineering Co | Polyesters |
| JPS61152795A (ja) * | 1984-12-27 | 1986-07-11 | Nippon Oil & Fats Co Ltd | 炭化水素−アルコ−ル混合燃料用添加剤 |
| JPS6218493A (ja) * | 1985-02-20 | 1987-01-27 | Lion Corp | 流動性向上剤 |
| JPS61207495A (ja) * | 1985-03-09 | 1986-09-13 | Toho Chem Ind Co Ltd | 燃料油用低温流動性改良剤 |
| CA1275403C (en) * | 1985-06-07 | 1990-10-23 | Albert Rossi | Lubricating oil composition containing dual additive combination for lowtemperature viscosity improvement |
| JPS62109892A (ja) * | 1985-11-07 | 1987-05-21 | Kao Corp | 燃料油用流動性改良剤 |
| JPS6357691A (ja) * | 1986-01-21 | 1988-03-12 | ポラ− モレクラ− コ−ポレ−シヨン | 燃料コンデイシヨナ |
| JPH01103699A (ja) * | 1987-07-28 | 1989-04-20 | Sumitomo Chem Co Ltd | 燃料油組成物 |
| DE3838918A1 (de) * | 1988-11-17 | 1990-05-23 | Basf Ag | Kraftstoffe fuer verbrennungsmaschinen |
| PL1801187T3 (pl) * | 2005-12-22 | 2016-04-29 | Clariant Produkte Deutschland | Oleje mineralne o polepszonej płynności w niskich temperaturach, zawierające dodatki detergentowe |
| DE102009035503A1 (de) * | 2009-07-31 | 2011-02-10 | Man Nutzfahrzeuge Ag | Verwendung von Polyoxymethylendi(alkylpolyglykol)ethern als Zusatz zu Dieselkraftstoffen zur Verminderung der Rußemission in Selbstzündungsmotoren |
| US10759989B2 (en) | 2016-01-06 | 2020-09-01 | Ecolab Usa Inc. | Temperature-stable paraffin inhibitor compositions |
| WO2017120287A1 (en) * | 2016-01-06 | 2017-07-13 | Ecolab Usa Inc. | Temperature-stable paraffin inhibitor compositions |
| US10858575B2 (en) | 2017-06-02 | 2020-12-08 | Championx Usa Inc. | Temperature-stable corrosion inhibitor compositions and methods of use |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB565465A (en) * | 1941-01-02 | 1944-11-13 | Standard Oil Dev Co | An improved manufacture of diesel fuels |
| FR1272980A (fr) * | 1960-08-22 | 1961-10-06 | British Petroleum Co | Produits synthétiques d'addition pour l'amélioration de la tenue au froid des fuel oils paraffiniques |
| US3047373A (en) * | 1959-12-21 | 1962-07-31 | Gulf Research Development Co | Fuel oils having improved combustion characteristics |
| US3132008A (en) * | 1960-08-22 | 1964-05-05 | British Petroleum Co | Fuel oil composition having reduced pour point |
| US3306856A (en) * | 1964-07-31 | 1967-02-28 | Exxon Research Engineering Co | Aryl keto acid pour-point depressants and dispersants for oleaginous compositions |
| US3762888A (en) * | 1970-11-16 | 1973-10-02 | Exxon Research Engineering Co | Fuel oil composition containing oil soluble pour depressant polymer and auxiliary flow improving compound |
| JPS52109506A (en) * | 1976-03-10 | 1977-09-13 | Dai Ichi Kogyo Seiyaku Co Ltd | W/o emulsion fuel of heavy oil |
| JPS5355305A (en) * | 1976-10-28 | 1978-05-19 | Dai Ichi Kogyo Seiyaku Co Ltd | Additive for finely powdered coal and oil mixture |
| JPS5419406A (en) * | 1977-07-15 | 1979-02-14 | Teikoku Piston Ring Co Ltd | Heattanddwear resistant sintered ferrous alloy for valve seat ring having good processability |
| JPS54155204A (en) * | 1978-05-25 | 1979-12-07 | Exxon Research Engineering Co | Multiiingredient additive combination for fuel oil and fuel oil containing it |
| JPS5594996A (en) * | 1979-01-10 | 1980-07-18 | Dai Ichi Kogyo Seiyaku Co Ltd | Slurry fuel additive |
-
1982
- 1982-03-30 RU SU3457843 patent/RU2014347C1/ru active
- 1982-03-30 CS CS225082A patent/CS276707B6/cs unknown
- 1982-03-31 HU HU82987A patent/HU202267B/hu not_active IP Right Cessation
- 1982-03-31 JP JP5363082A patent/JPS57177092A/ja active Granted
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB565465A (en) * | 1941-01-02 | 1944-11-13 | Standard Oil Dev Co | An improved manufacture of diesel fuels |
| US3047373A (en) * | 1959-12-21 | 1962-07-31 | Gulf Research Development Co | Fuel oils having improved combustion characteristics |
| FR1272980A (fr) * | 1960-08-22 | 1961-10-06 | British Petroleum Co | Produits synthétiques d'addition pour l'amélioration de la tenue au froid des fuel oils paraffiniques |
| US3132008A (en) * | 1960-08-22 | 1964-05-05 | British Petroleum Co | Fuel oil composition having reduced pour point |
| US3306856A (en) * | 1964-07-31 | 1967-02-28 | Exxon Research Engineering Co | Aryl keto acid pour-point depressants and dispersants for oleaginous compositions |
| US3762888A (en) * | 1970-11-16 | 1973-10-02 | Exxon Research Engineering Co | Fuel oil composition containing oil soluble pour depressant polymer and auxiliary flow improving compound |
| JPS52109506A (en) * | 1976-03-10 | 1977-09-13 | Dai Ichi Kogyo Seiyaku Co Ltd | W/o emulsion fuel of heavy oil |
| JPS5355305A (en) * | 1976-10-28 | 1978-05-19 | Dai Ichi Kogyo Seiyaku Co Ltd | Additive for finely powdered coal and oil mixture |
| JPS5419406A (en) * | 1977-07-15 | 1979-02-14 | Teikoku Piston Ring Co Ltd | Heattanddwear resistant sintered ferrous alloy for valve seat ring having good processability |
| JPS54155204A (en) * | 1978-05-25 | 1979-12-07 | Exxon Research Engineering Co | Multiiingredient additive combination for fuel oil and fuel oil containing it |
| JPS5594996A (en) * | 1979-01-10 | 1980-07-18 | Dai Ichi Kogyo Seiyaku Co Ltd | Slurry fuel additive |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2014347C1 (ru) | 1994-06-15 |
| HU202267B (en) | 1991-02-28 |
| CS276707B6 (en) | 1992-08-12 |
| JPS57177092A (en) | 1982-10-30 |
| CS8202250A2 (en) | 1991-07-16 |
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