EP2954035A1 - Procédé de préparation d'une graisse à base d'urée - Google Patents
Procédé de préparation d'une graisse à base d'uréeInfo
- Publication number
- EP2954035A1 EP2954035A1 EP14703097.7A EP14703097A EP2954035A1 EP 2954035 A1 EP2954035 A1 EP 2954035A1 EP 14703097 A EP14703097 A EP 14703097A EP 2954035 A1 EP2954035 A1 EP 2954035A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- compound
- grease
- carbon atoms
- urea
- 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
- 239000004519 grease Substances 0.000 title claims abstract description 63
- 239000004202 carbamide Substances 0.000 title claims abstract description 46
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- 239000002199 base oil Substances 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 77
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 239000000047 product Substances 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 4
- 238000000265 homogenisation Methods 0.000 claims description 3
- 238000005273 aeration Methods 0.000 claims description 2
- 125000005442 diisocyanate group Chemical group 0.000 abstract description 8
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 4
- 235000013877 carbamide Nutrition 0.000 description 38
- -1 nitro, hydroxyl Chemical group 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- XMKLTEGSALONPH-UHFFFAOYSA-N 1,2,4,5-tetrazinane-3,6-dione Chemical compound O=C1NNC(=O)NN1 XMKLTEGSALONPH-UHFFFAOYSA-N 0.000 description 13
- 239000006227 byproduct Substances 0.000 description 12
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 10
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- GABQKHQNXWNJJJ-UHFFFAOYSA-N diphenylcarbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)C1=CC=CC=C1 GABQKHQNXWNJJJ-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- BEQVQKJCLJBTKZ-UHFFFAOYSA-N diphenylphosphinic acid Chemical compound C=1C=CC=CC=1P(=O)(O)C1=CC=CC=C1 BEQVQKJCLJBTKZ-UHFFFAOYSA-N 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 230000035515 penetration Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000000732 arylene group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 239000012973 diazabicyclooctane Substances 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- DWLVWMUCHSLGSU-UHFFFAOYSA-M n,n-dimethylcarbamate Chemical compound CN(C)C([O-])=O DWLVWMUCHSLGSU-UHFFFAOYSA-M 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 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 2
- 239000000843 powder Substances 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- JXNPEDYJTDQORS-HZJYTTRNSA-N (9Z,12Z)-octadecadien-1-ol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCO JXNPEDYJTDQORS-HZJYTTRNSA-N 0.000 description 1
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- ZKXWKVVCCTZOLD-FDGPNNRMSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O ZKXWKVVCCTZOLD-FDGPNNRMSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- LMXOWXVJZDTLAD-UHFFFAOYSA-N dodecan-1-amine Chemical compound CCCCCCCCCCCCN.CCCCCCCCCCCCN LMXOWXVJZDTLAD-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- JXNPEDYJTDQORS-UHFFFAOYSA-N linoleyl alcohol Natural products CCCCCC=CCC=CCCCCCCCCO JXNPEDYJTDQORS-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910052961 molybdenite Inorganic materials 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- LBIYNOAMNIKVKF-FPLPWBNLSA-N palmitoleyl alcohol Chemical class CCCCCC\C=C/CCCCCCCCO LBIYNOAMNIKVKF-FPLPWBNLSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- WVNCFODWDVYKCA-UHFFFAOYSA-N tetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN.CCCCCCCCCCCCCCN WVNCFODWDVYKCA-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IKXFIBBKEARMLL-UHFFFAOYSA-N triphenoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=S)OC1=CC=CC=C1 IKXFIBBKEARMLL-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
-
- 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
- C10M115/00—Lubricating compositions characterised by the thickener being a non-macromolecular organic compound other than a carboxylic acid or salt thereof
- C10M115/08—Lubricating compositions characterised by the thickener being a non-macromolecular organic compound other than a carboxylic acid or salt thereof containing nitrogen
-
- 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
- C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
-
- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/02—Mixtures of base-materials and thickeners
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/10—Amides of carbonic or haloformic acids
- C10M2215/102—Ureas; Semicarbazides; Allophanates
- C10M2215/1026—Ureas; Semicarbazides; Allophanates used as thickening material
-
- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
-
- 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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
Definitions
- the invention relates to a process for preparing a urea grease.
- Urea greases are used in a variety of applications including bearings for constant-velocity joints, ball joints, wheel bearings, alternators, cooling fans, ball screws, linear guides of machine tools, sliding areas of construction equipment, and bearings and gears in steel equipment and various other industrial mechanical facilities. Urea greases typically have excellent heat and oxidation resistance, and can extend the lifetime of bearings .
- Urea greases contain low molecular weight organic compounds, sometimes referred to as polyureas, that are typically synthesized from isocyanates and amines.
- a diisocyanate and a monoamine can be used to form a diurea :
- a diisocyanate and a diamine can be used to form a tetraurea :
- a diisocyanate, an alcohol and a diamine can be used to form a triurea-urethane :
- Urea greases are formed by carrying out these reactions in a base oil, thereby directly providing the grease product wherein the urea thickener is dispersed throughout the base oil.
- the reaction of the diisocyanate and the amine does not require any heat and proceeds at a good rate at room temperature. There are no reaction byproducts that must be removed.
- the diisocyanate reagents are highly toxic and volatile and require special treatment and handling equipment. It is desirable to find an
- the invention provides a process for preparing a urea grease comprising one or more steps in which a compound of formula (I), a compound of formula (II) and a compound of formula (III) are reacted:
- R 1 and R 2 are chosen from hydrocarbyl having from 1 to 30 carbon atoms, or R 1 and R 2 are linked and form a hydrocarbylene group having from 1 to 30 carbon atoms, R 3 is chosen from hydrocarbyl comprising from 2 to 30 carbon atoms and R 4 is hydrocarbylene comprising from 2 to 30 carbon atoms;
- reaction steps wherein at least one of the reaction steps is carried out in the presence of a base oil.
- the process of the invention provides a urea grease, but avoids the use of diisocyanate reagents.
- Isocyanate-free syntheses of ureas are described by Luc Ubaghs in the PhD thesis "Isocyanate-free synthesis of (functional) polyureas, polyurethanes and urethane-containing
- urea greases may be prepared by reacting compounds (I), (II) and (III) wherein at least one of the reaction steps takes place in the presence of a base oil.
- FIG. 1 is a reaction scheme showing the
- FIG. 4 is a reaction scheme showing the
- hydrocarbyl refers to a monovalent organic radical comprising hydrogen and carbon and may be aliphatic, aromatic or alicyclic, for example, but not limited to, aralkyl, alkyl, aryl, cycloalkyl, alkylcycloalkyl, or a combination thereof, and may be saturated or olefinically unsaturated (one or more double-bonded carbons,
- hydrocarbylene refers to a divalent organic radical comprising hydrogen and carbon and may be aliphatic, aromatic or alicyclic, for example, but not limited to, aralkyl, alkyl, aryl, cycloalkyl or
- alkylcycloalkyl may be saturated or olefinically unsaturated (one or more double-bonded carbons,
- the invention provides a process for the preparation of a urea grease.
- a compound of formula (I), a compound of formula (II) and a compound of formula (III) are reacted :
- R 1 and R 2 are chosen from hydrocarbyl having from 1 to 30 carbon atoms, or R 1 and R 2 are linked and form a hydrocarbylene group having from 1 to 30 carbon atoms.
- R 1 and R 2 are preferably hydrocarbyl groups or a
- R 1 and R 2 are chosen from aryl having from 6 to 12 carbon atoms and alkyl having from 1 to 12 carbon atoms, or R 1 and R 2 are linked and form an alkylene group having from 1 to 12 carbon atoms.
- R 1 and R 2 are chosen from phenyl and substituted-phenyl groups having from 6 to 12 carbon atoms and alkyl groups having from 1 to 12 carbon atoms, or R 1 and R 2 are linked and form an alkylene group having from 1 to 6 carbon atoms .
- Substituted phenyl includes methyl-substituted or ethyl-substituted phenyl
- R 1 and R 2 are both phenyl or R 1 and R 2 are linked and form an ethylene group, i.e. the compound of formula (I) is diphenylene carbonate or ethylene carbonate.
- R 1 and R 2 are suitably chosen such that R 1_ OH and R 2 -OH (or HO-R 1 -R 2 -OH) are compounds that may be readily removed from the reaction mixture .
- R 3 is chosen from hydrocarbyl comprising from 2 to 30 carbon atoms.
- R 3 preferably comprises only hydrogen and carbon atoms, but it is possible that R 3 may also comprise heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents, particularly if R 3 is an aryl group.
- R 3 is aryl having from 6 to 12 carbon atoms or is alkyl comprising from 2 to 18 carbon atoms.
- the compound of formula (II) is chosen from octylamine, dodecylamine ( laurylamine ) , tetradecylamine (myristylamine ) , hexadecylamine,
- octadecylamine tallow amine, also referred to as stearylamine
- stearylamine oleylamine
- aniline benzyl amine
- p- toluidine p-chloro-aniline or m-xylidine.
- R 4 is hydrocarbylene comprising from 2 to 30 carbon atoms.
- R 4 preferably comprises only hydrogen and carbon atoms, but it is possible that R may also comprise heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents particularly if R 4 is an arylene group.
- R 4 is arylene comprising from 6 to 12 carbon atoms or alkylene comprising from 2 to 12 carbon atoms.
- the compound of formula (III) is chosen from arylene comprising from 6 to 12 carbon atoms Pre ow:
- a compound of formula (I), a compound of formula (II) and a compound of formula (III) are reacted in one step in the presence of a base oil.
- the reaction takes place in two steps and the second step takes place in the presence of a base oil.
- the process for preparing a urea grease comprises steps of:
- step (bl) reacting the product of step (al) with a compound of formula ( III ) :
- step (bl) is carried out in the presence of a base oil.
- the process for preparing a urea grease comprises steps of:
- step (b2) reacting the product of step (a2) with a compound of formula (II) :
- step (b2) is carried out in the presence of a base oil.
- step (al) the compound of formula (I) reacts with the compound of formula ( II ) :
- R 1 and R 2 are linked and form a hydrocarbylene group, then there will be just one product. If R 1 and R 2 are hydrocarbyl groups (and are not linked) , then an alcohol byproduct will result in step (al) and this byproduct is preferably removed before step (bl) .
- a diurea grease is suitably prepared by reacting compounds of formula (I) and (II) in step (al) and subsequently reacting the product of step (al) with a compound of formula (III) in step (bl) :
- step (al) the compounds of formula (I) and (II) are additionally reacted with a compound of formula (IV) :
- step (al) wherein R 5 is hydrocarbylene comprising from 2 to 30 carbon atoms.
- step (al) is then reacted with a compound of formula (III) in step (bl) :
- R 5 preferably comprises only hydrogen and carbon atoms, but it is possible that R 5 may also comprise heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents.
- R 5 is preferably arylene comprising from 6 to 12 carbon atoms or alkylene comprising from 2 to 12 carbon atoms.
- Preferred compounds of formula (IV) include ethylenediamine , propylenediamine,
- step (al) the compounds of formula (I) and (II) are additionally reacted with a compound of formula (V) and a compound of formula (VI) :
- R 6 and R 7 are independently chosen from
- step (al) hydrocarbyl comprising from 2 to 30 carbon atoms.
- step (al) hydrocarbyl comprising from 2 to 30 carbon atoms.
- step (bl) hydrocarbyl comprising from 2 to 30 carbon atoms.
- R 6 preferably comprises only hydrogen and carbon atoms, but it is possible that R 6 may also comprise heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents.
- R 6 is preferably alkylene or alkenylene comprising from 2 to 24 carbon atoms.
- Preferred compounds of formula (V) include 1-dodecanol (lauryl alcohol), 1-tetradecanol (myristyl alcohol), 1- hexadecanol (cetyl (or palmityl) alcohol), 1-octadecanol (stearyl alcohol), cis-9-octadecen-l-ol (oleyl alcohol), 9-octadecadien-l-ol (unsaturated palmitoleyl alcohol), 12-octadecadien-l-ol (linoleyl alcohol).
- R 7 preferably comprises only hydrogen and carbon atoms, but it is possible that R 7 may also comprise heteroatom substituents such as halo, nitro, hydroxyl or alkoxy substituents.
- R 7 preferably arylene comprising from 6 to 12 carbon atoms or alkylene comprising from 2 to 12 carbon atoms.
- Preferred compounds of formula (VI) include ethylenediamine , propylenediamine,
- step (bl) Before the product of step (al) is used in step (bl) it is preferable to remove any unreacted compounds of formula (I) and (II), any solvent that may have been used and any byproducts (especially R 1 -OH and R 2 -OH
- Removal is suitably achieved using vacuum.
- step (a2) the compound of formula (I) reacts with the compound of formula ( III ) :
- step (I) If R 1 and R 2 are linked and form a hydrocarbylene group, then there will be just one product. If R 1 and R 2 are hydrocarbyl groups (and are not linked) , then an alcohol byproduct will result in step (a2) and this byproduct is preferably removed before step (b2) .
- a diurea grease is suitably prepared by reacting compounds of formula (I) and (III) in step (a2) and subsequently reacting the product of step (a2) with a compound of formula (II) in step (b2) in the presence of a base oil:
- step (a2) the compounds of formula (I) and (III) are additionally reacted with a compound of formula (IV) :
- step (a2) the compound of formula (I) will react with the compound of formula (III), and the compound of formula (I) will react with the compound of formula (IV) .
- step (b2) the reaction products of step (a2) are then reacted with a compound of formula (II) :
- step (a2) the compounds of formula (I) and (III) are additionally reacted with compounds of formula (V) and (VI) :
- hydrocarbyl comprising from 2 to 30 carbon atoms.
- step (a2) the compound of formula (I) will react with the compound of formula (III), the compound of formula (I) will react with the compound of formula (V) and the compound of formula (I) will react with the compound of formula (VI) .
- step (b2) the reaction products of step (a2) are then reacted with a compound of formula (II) :
- step (b2) Before the product (s) of step (a2) is/are used in step (b2) it is preferable to remove any unreacted compounds of formula (I) and (III), any solvent that may have been used and any byproducts (especially R 1 -0H and R 2 -0H compounds). Removal is suitably achieved using vacuum or adequate solvent washes .
- step (al) and (a2) will be affected by the choice of the compound (I) . If compound (I) is diphenyl carbonate, then step (al) or (a2) preferably takes place without solvent or in the presence of a solvent such as toluene or
- the reaction preferably takes place in the presence of a catalyst such as diphenylphosphinic acid. Phenol will be produced as a byproduct of the reaction. The phenol byproduct should be removed, e.g. by use of a vacuum.
- a catalyst such as dibutyl tin methoxide, dibutyl tin dilaurate or tin (II) octoate .
- Other catalysts that could be used include potassium t- butoxide, copper (II) acetylacetonate, DABCO BLll and DABCO LV33.
- step (bl) and (b2) will be affected by the choice of the compound (I) .
- compound (I) is diphenyl carbonate then the reactants are preferably heated to at least 90°C and more preferably about 100°C. The reaction is preferably carried out in the absence of catalyst.
- compound (I) is dimethyl carbonate then the reactants are preferably heated to at least 130°C and more preferably about 140°C. The reaction is preferably carried out in the presence of a catalyst such as dibutyl tin dilaurate.
- a catalyst such as dibutyl tin dilaurate.
- the inventors have found that additional heating is often necessary to transform the reaction product of step (bl) or (b2) into a grease.
- the reaction products of step (bl) or (b2) are heated to at least 170°C and then cooled.
- the base oil that is present in at least one of the reaction steps may be of mineral origin, synthetic origin, or a combination thereof.
- Base oils of mineral origin may be mineral oils, for example, those produced by solvent refining or hydroprocessing .
- Base oils of synthetic origin may typically comprise mixtures of C ]_ Q -
- C50 hydrocarbon polymers for example, polymers of alpha- olefins, ester type synthetic oils, ether type synthetic oils, and combinations thereof.
- Base oils may also include Fischer-Tropsch derived highly paraffinic products .
- mineral base oils include paraffinic base oils and naphthenic base oils.
- Paraffinic base oils typically have a proportion of carbons in aromatic structure (Ca) in a range of from 1 to 10%, in naphthenic structure (Cn) in a range of from 20 to 30% and in paraffinic structure (Cp) in a range of from 60 to 70%.
- Naphthenic base oils typically have a proportion of carbons in aromatic structure (Ca) in a range of from 1 to 20%, in naphthenic structure (Cn) in a range of from
- Suitable examples of base oils include medium viscosity mineral oils, high viscosity mineral oils, and combinations thereof.
- Medium viscosity mineral oils have a viscosity generally in a range of from 5 mm 2 /s
- centistokes (cSt) at 100 °C to 15 mm 2 /s (cSt) at 100 °C preferably in a range of from 6 mm 2 /s (cSt) at 100 °C to 12 mm 2 /s (cSt) at 100 °C, and more preferably in a range of from 7 mm 2 /s (cSt) at 100 °C to 12 mm 2 /s (cSt) at 100 °C.
- High viscosity mineral oils have a viscosity generally in a range of from 15 mm 2 /s (cSt) at 100 °C to
- the urea grease that is the product of the process of the invention comprises a urea thickener and a base oil.
- the urea grease comprises a weight percent of urea based on the total weight of urea grease in a range of from 2 weight percent to 25 weight percent, more preferably in a range of from 3 weight percent to 20 weight percent, and most preferably in a range of from 5 weight percent to 20 weight percent.
- the product of the process of the invention is a urea grease.
- the base grease that results from step (bl) or step (b2) is subjected to further finishing procedures such as homogenisation, filtration and de- aeration .
- a urea grease prepared according to a process of the invention may comprise one or more additives, in amounts normally used in this field of application, to impart certain desirable characteristics to the urea grease including, for example, oxidation stability, tackiness, extreme pressure properties, corrosion inhibition, reduced friction and wear, and combinations thereof.
- the additives are preferably added to the base grease before the finishing procedures. Most preferably, the base grease is homogenised, then the additives are added, and then the grease is subjected to further homogenization .
- salicylates or alkylarylsulphonates ; one or more ashless dispersant additives, such as reaction products of polyisobutenyl succinic anhydride and an amine or ester; one or more antioxidants, such as hindered phenols or amines, for example phenyl alpha naphthylamine,
- diphenylamine or alkylated diphenylamine ; one or more antirust additives such as oxygenated hydrocarbons which have optionally been neutralised with calcium, calcium salts of alkylated benzene sulphonates and alkylated benzene petroleum sulphonates, and succinic acid
- Solid materials such as graphite, finely divided MoS 2 , talc, metal powders, and various polymers such as polyethylene wax may also be added to impart special properties .
- a urea grease prepared according to a process of the invention may comprise from 0.1 weight percent to 15 weight percent, preferably from 0.1 weight percent to 5 weight percent, more preferably from 0.1 weight percent to 2 weight percent, and even more preferably from 0.2 weight percent to 1 weight percent of one or more additives based on the total weight of urea grease.
- urea greases produced by the process of the invention are suitably used in typical applications for urea greases such as in constant-velocity joints, ball joints, wheel bearings, alternators, cooling fans, ball screws, linear guides of machine tools, sliding areas of construction equipment, and bearings and gears in steel equipment and various other industrial mechanical facilities .
- a urea grease may be prepared by a process comprising one or more steps in which a compound of formula (I), a compound of formula (II) and a compound of formula (III) are reacted:
- R 1 and R 2 are chosen from hydrocarbyl having from 1 to 30 carbon atoms, or R 1 and R 2 are linked and form a hydrocarbylene group having from 1 to 30 carbon atoms, R 3 is chosen from hydrocarbyl comprising from 2 to 30 carbon atoms and R 4 is hydrocarbylene comprising from 2 to 30 carbon atoms;
- the urea is synthesised from compounds (I), (II) and (III) and then the urea powder is dispersed in a base oil to form a grease.
- Figure 1 shows a process wherein diphenyl-carbonate (2) is reacted with ethylenediamine (4) and octylamine (1) without solvent under nitrogen atmosphere. After the reaction is completed the excess phenol is removed in vacuum. The two intermediates (3,5) are than combined to the final tetraurea (7) by introducing the methylene diphenyl diamine (6) under the same conditions and in the presence of a base oil. The reaction product is heated to 170°C to form a tetraurea grease.
- Figure 2 shows a process wherein octylamine (1) and ethylenediamine (4) are added to a ice-cooled solution of ethylenecarbonate (8) in water.
- the reaction is catalysed with (Bu 2 Sn (OMe ) 2 ) .
- the solvent and excess amines are removed under vacuum and the products 9 and 10 are isolated.
- the products 9 and 10 and the methylene diphenyl diamine (6) are connected at 150°C catalysed by
- resulting ethylene glycol is removed in vacuum.
- the reaction product is heated to 170°C to form a tetraurea grease.
- Figure 3 shows a process wherein dimethylcarbonate (1) and 4 , 4 ' -methylenedianiline (2) are reacted at 80°C in the presence of potassium t-butoxide. Methanol will be removed as a byproduct.
- the diphenylcarbamate product (3) is reacted with octylamine (4) in the presence of a base oil and dibutyltin dilaureate at 100°C to provide a grease product which is a diurea in base oil.
- the reaction product is heated to 170°C to form a diurea grease .
- FIG. 4 shows a process wherein diphenylcarbonate
- Example Id Step (b2) - Synthesis of Diurea in Base Oil lOlg of diphenylcarbamate, prepared according to Example la, was heated in base oil (506g) and octylamine (60g) overnight at 96 °C. The mixture was cooled and stirred with acetone (4x500ml), settled and decanted to remove phenol and by-products (according to NMR 95% pure) . The material was dried using a rotary evaporator and heated to 170°C then cooled down to form a grease. The properties of the grease were measured and are shown in Table 1.
- Example 2 One-Pot Two-Step Synthesis of Diurea in Base Oil
- the dicarbamate was reacted with octylamine for 2 hrs at 105 °C.
- the product was washed with dichloromethane and was then purified by crystallization from
- the delta penetration is as low as possible, and low values were achieved by some of the greases.
- the worked penetration values range from 247 to 340 which will give greases that would typically fall into the category of NLGI grade 1, 2 or 3.
- the dropping point is desirably as high as possible and several of the greases gave dropping points in excess of 300.
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Abstract
Priority Applications (1)
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EP14703097.7A EP2954035B1 (fr) | 2013-02-08 | 2014-02-07 | Procédé de préparation de graisse à base d'urée |
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EP13154677 | 2013-02-08 | ||
PCT/EP2014/052454 WO2014122273A1 (fr) | 2013-02-08 | 2014-02-07 | Procédé de préparation d'une graisse à base d'urée |
EP14703097.7A EP2954035B1 (fr) | 2013-02-08 | 2014-02-07 | Procédé de préparation de graisse à base d'urée |
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EP2954035A1 true EP2954035A1 (fr) | 2015-12-16 |
EP2954035B1 EP2954035B1 (fr) | 2016-12-21 |
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US (1) | US20160002557A1 (fr) |
EP (1) | EP2954035B1 (fr) |
JP (1) | JP6211100B2 (fr) |
CN (1) | CN104981536A (fr) |
BR (1) | BR112015017754A2 (fr) |
RU (1) | RU2646606C2 (fr) |
WO (1) | WO2014122273A1 (fr) |
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WO2018092806A1 (fr) * | 2016-11-16 | 2018-05-24 | 出光興産株式会社 | Composition de graisse pour équipement doté d'un dispositif d'alimentation en graisse automatique, et procédé de production associé |
JPWO2020218522A1 (fr) * | 2019-04-26 | 2020-10-29 | ||
JP7382250B2 (ja) | 2020-02-14 | 2023-11-16 | 株式会社ネオス | ポリウレアポリウレア化合物とこれを含む組成物ならびにポリウレア硬化物、およびポリウレア硬化物を含む成形フィルムならびに成形品 |
EP4186965A1 (fr) * | 2020-07-22 | 2023-05-31 | JTEKT Corporation | Matière première pour graisse, procédé de production de matière première de graisse, procédé de production de graisse et graisse |
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US2710841A (en) * | 1953-11-18 | 1955-06-14 | Standard Oil Co | Method of preparing substituted urea-thickened greases |
US3366662A (en) * | 1964-03-02 | 1968-01-30 | Olin Mathieson | Process for preparing isocyanates |
US3620695A (en) * | 1969-04-10 | 1971-11-16 | Texaco Inc | Thickened compositions and process of preparing them |
JPS62256892A (ja) * | 1986-04-30 | 1987-11-09 | Showa Shell Sekiyu Kk | グリ−ス組成物 |
US5248315A (en) * | 1990-11-15 | 1993-09-28 | Euron S.P.A. | Detergent additive for fuels |
DE4137852A1 (de) * | 1991-11-16 | 1993-05-19 | Basf Ag | Carbamidsaeureester, verfahren zu ihrer herstellung sowie kraft- und schmierstoffe, enthaltend die carbamidsaeureester |
JP3802616B2 (ja) * | 1996-08-19 | 2006-07-26 | シャープ株式会社 | インクジェット記録方法 |
US5863302A (en) * | 1997-04-18 | 1999-01-26 | Mobil Oil Corporation | Friction reducing additives for fuels and lubricants |
DE10351401A1 (de) * | 2003-11-04 | 2005-06-09 | Basf Ag | Hochfunktionelle, hochverzweigte Polyharnstoffe |
JP2006249271A (ja) * | 2005-03-11 | 2006-09-21 | Ntn Corp | グリース組成物およびグリース封入転がり軸受 |
JP4843260B2 (ja) * | 2005-06-10 | 2011-12-21 | Ntn株式会社 | 一方向クラッチ内蔵型回転伝達装置 |
JP4976795B2 (ja) * | 2006-09-21 | 2012-07-18 | 昭和シェル石油株式会社 | ウレアグリース組成物 |
WO2008040383A1 (fr) * | 2006-10-07 | 2008-04-10 | Gkn Driveline International Gmbh | Composition de graisse pour liaisons homocinétiques fonctionnant à vitesse constante, c comprenant au moins un composé de molybdène tri-nucléaire et un épaississant dérivé de l'urée |
JP4809793B2 (ja) * | 2007-03-08 | 2011-11-09 | 協同油脂株式会社 | グリース組成物及び機械部材 |
US8772210B2 (en) * | 2008-03-31 | 2014-07-08 | Exxonmobil Research And Engineering Company | High viscosity index PAO with polyurea thickeners in grease compositions |
US20100160198A1 (en) * | 2008-12-18 | 2010-06-24 | Chevron Oronite Company Llc | Friction modifiers and/or wear inhibitors derived from hydrocarbyl amines and cyclic carbonates |
US20120302782A1 (en) * | 2010-01-08 | 2012-11-29 | Yasuhito Yamamoto | Process for preparing a carbamate compound |
CN102382707B (zh) * | 2010-08-31 | 2014-07-02 | 中国石油化工股份有限公司 | 一种四脲润滑脂及其制备方法 |
CN102899125B (zh) * | 2011-07-29 | 2014-04-02 | 中国石油天然气股份有限公司 | 一种具有优异剪切性能的聚脲润滑脂的制备方法 |
US9012676B2 (en) * | 2011-09-22 | 2015-04-21 | Great Eastern Resins Industrial Co., Ltd. | Processes for producing aryl carbamates, isocynates and polyureas using diaryl carbonate |
-
2014
- 2014-02-07 BR BR112015017754A patent/BR112015017754A2/pt not_active Application Discontinuation
- 2014-02-07 CN CN201480007940.1A patent/CN104981536A/zh active Pending
- 2014-02-07 WO PCT/EP2014/052454 patent/WO2014122273A1/fr active Application Filing
- 2014-02-07 EP EP14703097.7A patent/EP2954035B1/fr active Active
- 2014-02-07 US US14/765,946 patent/US20160002557A1/en not_active Abandoned
- 2014-02-07 RU RU2015138152A patent/RU2646606C2/ru active
- 2014-02-07 JP JP2015556509A patent/JP6211100B2/ja active Active
Non-Patent Citations (1)
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See references of WO2014122273A1 * |
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RU2015138152A (ru) | 2017-03-16 |
JP2016506985A (ja) | 2016-03-07 |
US20160002557A1 (en) | 2016-01-07 |
RU2646606C2 (ru) | 2018-03-06 |
JP6211100B2 (ja) | 2017-10-11 |
WO2014122273A1 (fr) | 2014-08-14 |
BR112015017754A2 (pt) | 2017-07-11 |
EP2954035B1 (fr) | 2016-12-21 |
CN104981536A (zh) | 2015-10-14 |
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