JP5908786B2 - イミド−アミド化合物及びその製造方法、グリース用増ちょう剤並びにグリース組成物 - Google Patents
イミド−アミド化合物及びその製造方法、グリース用増ちょう剤並びにグリース組成物 Download PDFInfo
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- JP5908786B2 JP5908786B2 JP2012113432A JP2012113432A JP5908786B2 JP 5908786 B2 JP5908786 B2 JP 5908786B2 JP 2012113432 A JP2012113432 A JP 2012113432A JP 2012113432 A JP2012113432 A JP 2012113432A JP 5908786 B2 JP5908786 B2 JP 5908786B2
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- Prior art keywords
- imide
- monoamine
- general formula
- represented
- grease
- 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.)
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- 239000004519 grease Substances 0.000 title claims description 52
- 238000000034 method Methods 0.000 title description 6
- -1 imide carboxylic acid Chemical class 0.000 claims description 51
- 239000002562 thickening agent Substances 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 33
- 125000001931 aliphatic group Chemical group 0.000 claims description 23
- 125000002723 alicyclic group Chemical group 0.000 claims description 19
- 239000002199 base oil Substances 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000012948 isocyanate Substances 0.000 claims description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000001050 lubricating effect Effects 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims description 3
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 claims description 3
- LNWBFIVSTXCJJG-UHFFFAOYSA-N [diisocyanato(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(N=C=O)(N=C=O)C1=CC=CC=C1 LNWBFIVSTXCJJG-UHFFFAOYSA-N 0.000 claims description 3
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000005442 diisocyanate group Chemical group 0.000 description 17
- 125000000962 organic group Chemical group 0.000 description 16
- 239000000344 soap Substances 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 15
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- 239000004202 carbamide Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 150000003672 ureas Chemical class 0.000 description 6
- 150000003673 urethanes Chemical class 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 3
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000000434 field desorption mass spectrometry Methods 0.000 description 3
- 125000005462 imide group Chemical group 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 0 *N(C(c(cc1)c2cc1C(O)=O)=O)C2=O Chemical compound *N(C(c(cc1)c2cc1C(O)=O)=O)C2=O 0.000 description 2
- XMKLTEGSALONPH-UHFFFAOYSA-N 1,2,4,5-tetrazinane-3,6-dione Chemical class O=C1NNC(=O)NN1 XMKLTEGSALONPH-UHFFFAOYSA-N 0.000 description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PIXITTJSTHVOBB-UHFFFAOYSA-N C(CCCCC)C1(CCCCC1)N=C=O Chemical compound C(CCCCC)C1(CCCCC1)N=C=O PIXITTJSTHVOBB-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002396 Polyurea Chemical class 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000003975 aryl alkyl amines Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- ZAZKJZBWRNNLDS-UHFFFAOYSA-N methyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC ZAZKJZBWRNNLDS-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-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
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- WTEWDKVXORBINR-UHFFFAOYSA-N 1,3-bis(3-isocyanatophenoxy)benzene Chemical compound O=C=NC1=CC=CC(OC=2C=C(OC=3C=C(C=CC=3)N=C=O)C=CC=2)=C1 WTEWDKVXORBINR-UHFFFAOYSA-N 0.000 description 1
- ZTASCEXPRIMSJO-UHFFFAOYSA-N 1,3-bis(4-isocyanatophenoxy)benzene Chemical compound C1=CC(N=C=O)=CC=C1OC1=CC=CC(OC=2C=CC(=CC=2)N=C=O)=C1 ZTASCEXPRIMSJO-UHFFFAOYSA-N 0.000 description 1
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- JFRQLKNEDLLXOQ-UHFFFAOYSA-N 1,3-diisocyanato-2,4-dimethylbenzene Chemical compound CC1=CC=C(N=C=O)C(C)=C1N=C=O JFRQLKNEDLLXOQ-UHFFFAOYSA-N 0.000 description 1
- MLXLDKWQJYBKOH-UHFFFAOYSA-N 1,3-diisocyanatoadamantane Chemical compound C1C(C2)CC3CC1(N=C=O)CC2(N=C=O)C3 MLXLDKWQJYBKOH-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
- ABUJJNMWUJEMTQ-UHFFFAOYSA-N 1,4-bis(4-isocyanatophenoxy)benzene Chemical compound C1=CC(N=C=O)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N=C=O)C=C1 ABUJJNMWUJEMTQ-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SIZPGZFVROGOIR-UHFFFAOYSA-N 1,4-diisocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=C(N=C=O)C2=C1 SIZPGZFVROGOIR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- HWHSCZHXWXLWPB-UHFFFAOYSA-N 1,6-diisocyanato-2,5-dimethylhexane Chemical compound O=C=NCC(C)CCC(C)CN=C=O HWHSCZHXWXLWPB-UHFFFAOYSA-N 0.000 description 1
- QLVWISADYMNPPU-UHFFFAOYSA-N 1,6-diisocyanato-3-methoxyhexane Chemical compound O=C=NCCC(OC)CCCN=C=O QLVWISADYMNPPU-UHFFFAOYSA-N 0.000 description 1
- BQCFLYDPYLZXRU-UHFFFAOYSA-N 1,7-diisocyanato-2,5-dimethylheptane Chemical compound O=C=NCCC(C)CCC(C)CN=C=O BQCFLYDPYLZXRU-UHFFFAOYSA-N 0.000 description 1
- AFAHGHSCBIDDFD-UHFFFAOYSA-N 1,7-diisocyanato-3-methylheptane Chemical compound O=C=NCCC(C)CCCCN=C=O AFAHGHSCBIDDFD-UHFFFAOYSA-N 0.000 description 1
- UTFSEWQOIIZLRH-UHFFFAOYSA-N 1,7-diisocyanatoheptane Chemical compound O=C=NCCCCCCCN=C=O UTFSEWQOIIZLRH-UHFFFAOYSA-N 0.000 description 1
- BWQRHFZDSWATJG-UHFFFAOYSA-N 1,8-diisocyanatonaphthalene Chemical compound C1=CC(N=C=O)=C2C(N=C=O)=CC=CC2=C1 BWQRHFZDSWATJG-UHFFFAOYSA-N 0.000 description 1
- QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 description 1
- MIDIHVRZNKERPO-UHFFFAOYSA-N 1,9-diisocyanato-5-methylnonane Chemical compound O=C=NCCCCC(C)CCCCN=C=O MIDIHVRZNKERPO-UHFFFAOYSA-N 0.000 description 1
- GHSZVIPKVOEXNX-UHFFFAOYSA-N 1,9-diisocyanatononane Chemical compound O=C=NCCCCCCCCCN=C=O GHSZVIPKVOEXNX-UHFFFAOYSA-N 0.000 description 1
- URQYPXQXSVUVRG-UHFFFAOYSA-N 1-(5-chloro-2,4-dimethoxyphenyl)-3-(5-cyanopyrazin-2-yl)urea Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=O)NC1=CN=C(C#N)C=N1 URQYPXQXSVUVRG-UHFFFAOYSA-N 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
- YPMOSINXXHVZIL-UHFFFAOYSA-N sulfanylideneantimony Chemical compound [Sb]=S YPMOSINXXHVZIL-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
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- 238000005292 vacuum distillation Methods 0.000 description 1
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- 150000003752 zinc compounds Chemical class 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- 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
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- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/0406—Ethers; Acetals; Ortho-esters; Ortho-carbonates used as base material
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- C—CHEMISTRY; METALLURGY
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/08—Amides
- C10M2215/0813—Amides used as thickening agents
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- 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
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- 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
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/02—Bearings
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
- Indole Compounds (AREA)
- Rolling Contact Bearings (AREA)
Description
[式中、R1及びR2は1価の有機基を示し、X1は2価の有機基を示し、X2は1価の有機基を示し、式(2)中のR1及びR2は同一でも異なっていてもよい。]
を備えるイミド化合物の製造方法を提供する。
[式中、R及びXはそれぞれ1価の有機基を示す。]
[式中、R1及びR2は1価の有機基を示し、X1は2価の有機基を示し、X2は1価の有機基を示し、式(2)中のR1及びR2は同一でも異なっていてもよい。]
本発明の第2実施形態に係るイミド−アミド化合物の製造方法は、下記式(4)で表されるトリメリット酸無水物と下記一般式(5)で表されるモノアミンとを反応させて下記一般式(6)で表されるイミドカルボン酸を得る第1の工程と、前記イミドカルボン酸と下記一般式(7)で表されるイソシアネートとを反応させて下記一般式(1)で表されるイミド−アミド化合物を得る第2の工程と、を備える。
[式中、R及びXはそれぞれ1価の有機基を示す。]
[式中、R1及びR2は1価の有機基を示し、X1は2価の有機基を示し、X2は1価の有機基を示し、式(2)中のR1及びR2は同一でも異なっていてもよい。]
本発明の第3実施形態に係るグリース用増ちょう剤は、上記一般式(1)で表されるイミド−アミド化合物を含有する。なお、一般式(1)で表されるイミド−アミド化合物の具体例及び好ましい例は第1実施形態に係るイミド−アミド化合物の具体例及び好ましい例と同様である。
本発明の第4実施形態に係るグリース組成物は、潤滑油基油と、上記一般式(1)で表されるイミド−アミド化合物とを含有し、該イミド−アミド化合物の含有量がグリース組成物全量基準で2〜50質量%のものである。
NMP(N−メチル−2−ピロリドン)溶媒250mL中にて、下記式(4)で表されるトリメリット酸無水物43.8gと下記式(10)で表されるドデシルアミン42.3gとを冷却しながら25℃で4時間反応させた。続いて、トルエン250mLを加えて還流温度でディーンスターク装置を用い共沸脱水しながら4時間加熱した。減圧蒸留を行い、トルエンとNMP150mlを除き、冷却後析出した固体をトルエン100mL、メタノール100mLで洗浄および減圧乾燥したところ、下記式(11)で表されるイミドカルボン酸中間体を含むイミドカルボン酸中間体−1を固形物として得た(収量:50.0g)。続いて、NMP(N−メチル−2−ピロリドン)溶媒15mL中にて、この中間体15.0gと下記式(12)で表される2,4−ジイソシアナトトルエン2.9gと下記式(13)で表される2,6−ジイソシアナトトルエン0.7gの混合物とを160℃で2時間反応させた。室温まで冷却後、トルエン30mLを加えけん濁させた後、固体をろ過し、トルエン100mlアセトン100mLで洗浄および乾燥したところ、下記式(14)で表されるイミド−アミド化合物を含むイミド−アミド化合物−1を固形物として得た(収量:14.3g)。
実施例2〜18においてはそれぞれ、一般式(4)で表されるモノアミンとして上記式(10)〜(12)又は下記式(15)〜(18)で表されるモノアミンを、一般式(8)で表されるジイソシアネートとして上記式(12)、(13)又は下記式(19)〜22)で表されるジイソシアネートを、表1〜6に示す組合せで用いたこと以外は実施例1と同様にして、イミド化合物−2〜18を固形物として得た。実施例5〜7および14、16は2種類のモノアミンを用いているが、それぞれの中間体を実施例1と同様に合成した後、モル比で1:1、かつ2種類の中間体を合せた重量が15gになる量の中間体とジイソシアネートを実施例1と同様に反応させた。反応後に固体が析出しない場合は、固体が析出するまでメタノールを添加した。反応で得られたイミド化合物−2〜18の収量を表1〜6に示す。
4,4’−ジイソシアナトジフェニルメタン55.8gに対し、シクロヘキシルアミン44.2gを100℃動粘度が13mm2/sのジフェニルエーテル基油300g中にて反応させグリース状物質を得た。グリース状物質からヘキサンにてジフェニルエーテル基油を除去し、式(40)で表されるウレア化合物−1を得た。得られたウレア化合物の収量を表7に示す。
4,4’−ジイソシアナトジフェニルメタン31.7gに対し、オクタデシルアミン68.3gを100℃動粘度が13mm2/sのジフェニルエーテル基油300g中にて反応させグリース状物質を得た。グリース状物質からヘキサンにてジフェニルエーテル基油を除去し、式(41)で表されるウレア化合物−2を得た。得られたウレア化合物の収量を表7に示す。
実施例1〜18で得られたイミド-アミド化合物−1〜18及び比較例1、2で得られたウレア化合物−1、2を、熱分析装置(島津製作所製DTG60、昇温速度:5℃/分、雰囲気ガス:窒素)にて5%分解温度を測定した。得られた結果を表8〜14に示す。表中、分解温度が高いほど耐熱性に優れることを意味する。
実施例1〜18で得られたイミド-アミド化合物−1〜18及び比較例1、2で得られたウレア化合物−1、2を、それぞれ25重量%になるよう100℃動粘度が13mm2/sのジフェニルエーテル基油に混合し、ロールミルを通し基油中に均一に分散し得られた物質を、JIS2220のちょう度測定法により60混和(60W)後のちょう度の測定をした。得られた結果を表8〜14に示す。なお、比較例1、2のウレア化合物に関しては、ヘキサンにてジフェニルエーテル基油を除去する前にちょう度を測定した。
Claims (5)
- 前記一般式(2)中、R 1 及びR 2 は、炭素数4〜20の脂肪族モノアミン、又は炭素数4〜20の脂環式モノアミンから1つのアミノ基を除いた1価の残基を示し、X 1 は、ジイソシアナトトルエン、ジイソシアナトジフェニルメタン若しくはこれらの誘導体、フェニレンジイソシアネート、又はキシリレンジイソシアネートから2つのイソシアネート基を除いた2価の残基を示す、請求項2に記載のグリース用増ちょう剤。
- 下記式(4)で表されるトリメリット酸無水物と下記一般式(5)で表されるモノアミンとを反応させて下記一般式(6)で表されるイミドカルボン酸を得る第1の工程と、
前記イミドカルボン酸と芳香族ジイソシアネートとを反応させて下記一般式(2)で表されるイミド−アミド化合物を得る第2の工程と、
前記イミド−アミド化合物を含有するグリース用増ちょう剤を調製する第3の工程と、
を備えるグリース用増ちょう剤の製造方法。
[式中、Rは、脂肪族モノアミン、脂環式モノアミン又は芳香族モノアミンから1つのアミノ基を除いた1価の残基を示し、R 1 及びR 2 は、脂肪族モノアミン、脂環式モノアミン又は芳香族モノアミンから1つのアミノ基を除いた1価の残基を示し、X 1 は、芳香族ジイソシアネートから2つのイソシアネート基を除いた2価の残基を示し、式(2)中のR1及びR2は同一でも異なっていてもよい。] - 潤滑油基油と、請求項2又は3に記載のグリース用増ちょう剤とを含有するグリース組成物。
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |