CN117946020A - Isocyanurate compound and preparation method and application thereof - Google Patents
Isocyanurate compound and preparation method and application thereof Download PDFInfo
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- CN117946020A CN117946020A CN202410096815.8A CN202410096815A CN117946020A CN 117946020 A CN117946020 A CN 117946020A CN 202410096815 A CN202410096815 A CN 202410096815A CN 117946020 A CN117946020 A CN 117946020A
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- -1 Isocyanurate compound Chemical class 0.000 title claims abstract description 84
- 238000002360 preparation method Methods 0.000 title abstract description 31
- 239000004519 grease Substances 0.000 claims abstract description 61
- 230000001050 lubricating effect Effects 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 125000001033 ether group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 68
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 29
- 229920013639 polyalphaolefin Polymers 0.000 claims description 24
- 239000002199 base oil Substances 0.000 claims description 18
- 150000004820 halides Chemical class 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- 238000006467 substitution reaction Methods 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 13
- 239000003963 antioxidant agent Substances 0.000 claims description 13
- 230000003078 antioxidant effect Effects 0.000 claims description 12
- 239000002562 thickening agent Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000013556 antirust agent Substances 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 239000012535 impurity Substances 0.000 claims description 3
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 150000001805 chlorine compounds Chemical group 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000003973 paint Substances 0.000 claims 1
- 239000000084 colloidal system Substances 0.000 abstract description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 abstract description 3
- 238000005507 spraying Methods 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000012360 testing method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 10
- 230000035515 penetration Effects 0.000 description 10
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 238000005299 abrasion Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 229920002396 Polyurea Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000012512 characterization method Methods 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 5
- 239000011968 lewis acid catalyst Substances 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000012964 benzotriazole Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000005461 lubrication Methods 0.000 description 4
- 230000001007 puffing effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NZUPFZNVGSWLQC-UHFFFAOYSA-N 1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound BrCC(Br)CN1C(=O)N(CC(Br)CBr)C(=O)N(CC(Br)CBr)C1=O NZUPFZNVGSWLQC-UHFFFAOYSA-N 0.000 description 3
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 3
- NZWIYPLSXWYKLH-UHFFFAOYSA-N 3-(bromomethyl)heptane Chemical compound CCCCC(CC)CBr NZWIYPLSXWYKLH-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 150000001923 cyclic compounds 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
- 238000001035 drying Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000012968 metallocene catalyst Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 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 3
- 238000005406 washing Methods 0.000 description 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- VOHILFSOWRNVJJ-UHFFFAOYSA-N 2-(bromomethyl)oxolane Chemical compound BrCC1CCCO1 VOHILFSOWRNVJJ-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 101100407037 Oryza sativa subsp. japonica PAO6 gene Proteins 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 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
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 1
- KYIMHWNKQXQBDG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC Chemical compound N=C=O.N=C=O.CCCCCC KYIMHWNKQXQBDG-UHFFFAOYSA-N 0.000 description 1
- DGOMVSNLFKNSAR-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCCCCCC Chemical compound N=C=O.N=C=O.CCCCCCCCCC DGOMVSNLFKNSAR-UHFFFAOYSA-N 0.000 description 1
- PQKRXFRMEHADAK-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCCCCCCCCCCCCCC Chemical compound N=C=O.N=C=O.CCCCCCCCCCCCCCCCCC PQKRXFRMEHADAK-UHFFFAOYSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 229910010062 TiCl3 Inorganic materials 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000011954 Ziegler–Natta catalyst Substances 0.000 description 1
- 239000006230 acetylene black Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- JHXKRIRFYBPWGE-UHFFFAOYSA-K bismuth chloride Chemical compound Cl[Bi](Cl)Cl JHXKRIRFYBPWGE-UHFFFAOYSA-K 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- IKZBVTPSNGOVRJ-UHFFFAOYSA-K chromium(iii) phosphate Chemical class [Cr+3].[O-]P([O-])([O-])=O IKZBVTPSNGOVRJ-UHFFFAOYSA-K 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical group C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- PPDADIYYMSXQJK-UHFFFAOYSA-N trichlorosilicon Chemical compound Cl[Si](Cl)Cl PPDADIYYMSXQJK-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Landscapes
- Lubricants (AREA)
Abstract
The invention provides an isocyanurate compound, a preparation method and application thereof, wherein the structural formula of the isocyanurate compound is shown in a formula III: Wherein R 1、R3 is independently selected from an ether group with 1-30 carbon atoms and/or an alkyl group, and R 2 is selected from an ether group with 1-30 carbon atoms. The invention provides an isocyanurate compound, a preparation method and application thereof, wherein the isocyanurate is used for preparing lubricating grease, and the mechanical shear stability, colloid stability, anti-friction performance, service life and anti-water-spraying performance of the lubricating grease are improved.
Description
Technical Field
The invention relates to the field of chemical industry, in particular to an isocyanurate compound, a preparation method and application thereof.
Background
The lubricating grease is used for reducing mechanical friction and abrasion, prolonging the service life of mechanical equipment, and about 80% of rolling bearings on the market are lubricated by the lubricating grease. The modern precision bearings have more and more severe use conditions and higher requirements on lubricating grease, and are mainly characterized by long service life, adaptability to high/low temperature, high/low speed use, low noise and the like.
The common low-noise lubricating grease products at home and abroad are mostly lithium grease and polyurea grease. The common lithium-based grease sold in the market has better noise reduction effect at the beginning, but the noise becomes large after a period of operation, and the polyurea grease has excellent low noise performance, heat stability, colloid stability and oxidation stability, and also has long service life, and particularly has outstanding effect at high temperature. Although many of the properties of polyurea grease are excellent, poor shear stability is one of its major drawbacks, usually manifested by severe softening at low shear rates, and after 10 ten thousand operations of an ASTM grease worker, the change in cone penetration is around 100 units, and a significant decrease in cone penetration results in loss of grease in bearings, losing lubrication effect, thus limiting the application of polyurea grease.
Disclosure of Invention
In view of the above-described drawbacks of the prior art, an object of the present invention is to provide an isocyanurate compound, a method for preparing the same, and a use thereof, for solving the problems of the prior art.
To achieve the above and other related objects, the present invention is achieved by the following technical means.
The invention provides an isocyanurate compound, which has a structural formula shown in a formula III:
Wherein R 1、R3 is independently selected from an ether group with 1-30 carbon atoms and/or an alkyl group, and R 2 is selected from an ether group with 1-30 carbon atoms.
The carbon number of R 1、R3 may be 1 to2, 2 to 3, 3 to 5, 5 to 7, 7 to 8, 8 to 12, 12 to 16, 16 to 25, 25 to 30. Preferably, R 1、R3 has 1 to 12 carbon atoms.
The carbon number of R 2 may be 1 to2, 2 to 3, 3 to 5, 5 to 7, 7 to 8, 8 to 10, 10 to 16, 16 to 25, 25 to 30. Preferably, R 2 has 1 to 12 carbon atoms.
Preferably, R 1、R3 further contains an alicyclic hydrocarbon group and/or a heterocyclic group. More preferably, the alicyclic hydrocarbon group is a multi-membered monocyclic and/or polycyclic structure. More preferably, the heterocyclic group is a heteroatom (non-carbon atom) -containing cyclic compound.
Preferably, R 1、R3 is branched or straight chain.
Preferably, R 2 further contains an alicyclic hydrocarbon group and/or a heterocyclic group. More preferably, the alicyclic hydrocarbon group is a polycyclic and/or polycyclic structure. More preferably, the heterocyclic group is a heteroatom (non-carbon atom) -containing cyclic compound.
Preferably, the isocyanurate compound includes a compound of formula III-1, a compound of formula III-2, a compound of formula III-3, a compound of formula III-4; the structural formulas of the compound of the formula III-1, the compound of the formula III-2, the compound of the formula III-3 and the compound of the formula III-4 are shown as follows:
Wherein R' 1、R'2、R'3 is independently selected from an ether group and/or an alkyl group having 1 to 10 carbon atoms, and R 0 is selected from an ether group and/or an alkyl group having 1 to 20 carbon atoms.
Preferably, R' 1、R'2、R'3 and R 0 also contain alicyclic hydrocarbon groups and/or heterocyclic groups. More preferably, the alicyclic hydrocarbon group is a polycyclic and/or polycyclic structure. More preferably, the heterocyclic group is a heteroatom (non-carbon atom) -containing cyclic compound.
Preferably, R' 1、R'2、R'3 and R 0 are branched or straight chain.
R' 1、R'2、R'3 may have 1 to 2,2 to 3, 3 to 5,5 to 7, and 7 to 10 carbon atoms. Preferably, R' 1、R'2、R'3 has 1 to 4 carbon atoms.
The number of carbon atoms of R 0 may be 1 to 8,8 to 15, 15 to 20. Preferably, R 0 has 1 to 8 carbon atoms.
More preferably, in the compounds of formula III-1, R' 1 has the formula:
more preferably, in the compounds of formula III-2, R' 1 has the formula:
more preferably, in the compounds of formula III-3, R' 1 has the formula:
More preferably, in the compounds of formula III-1, R' 2 has the formula:
more preferably, in the compounds of formula III-2, R' 2 has the formula:
more preferably, in the compounds of formula III-3, R' 2 has the formula:
more preferably, in the compounds of formula III-1, R' 3 has the formula:
More preferably, in the compounds of formula III-2, R' 3 has the formula:
More preferably, in the compounds of formula III-3, R' 3 has the formula:
more preferably, in the compounds of formula III-1, R' 0 has the formula:
more preferably, in the compounds of formula III-2, R' 0 has the formula:
More preferably, in the compounds of formula III-3, R' 0 has the formula:
preferably, the compound of formula III-1 comprises:
more preferably, the compound of formula III-2 comprises:
more preferably, the compound of formula III-3 comprises:
the invention also discloses a preparation method of the isocyanurate compound, which comprises the following steps: the alcohol and the halide undergo substitution reaction to prepare the isocyanurate compound.
Preferably, the halide is selected from chloride, bromide or iodide.
Preferably, the reaction system comprises a hydrogen drawing agent, wherein the hydrogen drawing agent is selected from one or more of lithium diisopropylamide, n-butyllithium, tertiary butyllithium, sodium hydride, potassium carbonate, sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, sodium tert-butoxide and potassium tert-butoxide. More preferably sodium hydride. The hydrogen extracting agent is used for promoting the dehydrogenation of alcohol.
More preferably, the molar ratio of the hydrogen extracting agent to the hydroxyl group is (0.3-1.5): 1, more preferably (0.5 to 1.5): 1.
More preferably, the addition temperature of the hydrogen drawing agent is 0-5 ℃.
Preferably, the reaction system comprises a reaction medium selected from one or more of N, N-dimethylformamide, dimethylsulfoxide, acetonitrile and acetone.
More preferably, the reaction medium is selected from one or both of acetonitrile and acetone.
Preferably, the reaction temperature is not less than 40 ℃.
More preferably, the reaction temperature is 40 to 90 ℃. For example, the temperature may be 50℃at 55℃at 60℃at 75℃at 78℃at 80 ℃.
Preferably, the reaction time is (8-20) h.
Preferably, the reaction process further comprises a post-treatment step comprising separation and removal of impurities. More preferably, the separation is performed by quenching the reaction while forming a layer, and then separating the liquid to obtain an organic phase. Further preferably, the aqueous phase is extracted with ethyl acetate and the organic phases are combined. More preferably, the removing impurities includes one or more of water washing, drying, suction filtration and evaporation. Further preferably, the washing is washing the organic phase with water and/or saturated saline, respectively. Further preferably, the drying is drying the organic phase with anhydrous magnesium sulfate. Further preferably, the suction filtration is solid-liquid separation of the organic phase added with the desiccant to extract the organic phase. Further preferably, the evaporation is to remove the solvent by a rotary evaporator, the evaporation temperature is 40-60 ℃, and the vacuum degree is 0.1-10 KPa.
Preferably, when the isocyanurate compound has the structural formula III-1, the preparation method thereof is as follows:
The alcohol and halide are subjected to substitution reaction to prepare isocyanurate compound, and the reaction route is as follows:
more preferably, the molar ratio of the compound of formula I to the compound of formula II is (2.0 to 7.5): 1. more preferably (2.2 to 7.0): 1.
Preferably, when the isocyanurate compound has the structural formula III-1, the preparation method thereof is as follows:
The alcohol and halide are subjected to substitution reaction to prepare isocyanurate compound, and the reaction route is as follows:
More preferably, the molar ratio of the compound of formula II '-1 to the compound of formula I' is (2.0 to 7.5): 1. more preferably (2.2 to 7.0): 1.
More preferably, the compound of formula I-1 comprises
More preferably, the compound of formula II comprises bromo-n-butane, bromo-n-hexane, bromo-isooctane or 2-bromomethyltetrahydrofuran.
Preferably, when the isocyanurate compound has the structural formula III-2, the preparation method thereof is as follows:
The alcohol and halide are subjected to substitution reaction to prepare isocyanurate compound, and the reaction route is as follows:
More preferably, the molar ratio of the compound of formula I-2 to the compound of formula II is from (2.0 to 7.5): 1. more preferably (2.2 to 7.0): 1.
Preferably, when the isocyanurate compound has the structural formula III-2, the preparation method thereof is as follows:
The alcohol and halide are subjected to substitution reaction to prepare isocyanurate compound, and the reaction route is as follows:
More preferably, the molar ratio of the compound of formula II '-2 to the compound of formula I' is (2.0 to 7.5): 1. more preferably (2.2 to 7.0): 1.
More preferably, the compound of formula II' -2 comprises
More preferably, the compounds of formula I' include
Preferably, when the isocyanurate compound has the structural formula III-3, the preparation method thereof is as follows:
The alcohol and halide are subjected to substitution reaction to prepare isocyanurate compound, and the reaction route is as follows:
more preferably, the molar ratio of the compound of formula I-3 to the compound of formula II is from (2.0 to 7.5): 1. more preferably (2.2 to 7.0): 1.
Preferably, when the isocyanurate compound has the structural formula III-3, the preparation method thereof is as follows:
The alcohol and halide are subjected to substitution reaction to prepare isocyanurate compound, and the reaction route is as follows:
more preferably, the molar ratio of the compound of formula II '-3 to the compound of formula I' is (2.0 to 7.5): 1. more preferably (2.2 to 7.0): 1.
More preferably, the compound of formula I-3 comprises
Preferably, when the isocyanurate compound has the structural formula III-4, the preparation method thereof is as follows:
The alcohol and halide are subjected to substitution reaction to prepare isocyanurate compound, and the reaction route is as follows:
More preferably, the molar ratio of the compound of formula I-4 to the compound of formula II is from (2.0 to 7.5): 1. more preferably (2.2 to 7.0): 1.
Preferably, when the isocyanurate compound has the structural formula III-4, the preparation method thereof is as follows:
The alcohol and halide are subjected to substitution reaction to prepare isocyanurate compound, and the reaction route is as follows:
More preferably, the molar ratio of the compound of formula II '-4 to the compound of formula I' is (2.0 to 7.5): 1. more preferably (2.2 to 7.0): 1.
More preferably, when the isocyanurate compound has the structural formula III-1-1, the preparation method thereof is as follows:
The alcohol and halide are subjected to substitution reaction to prepare isocyanurate compound, and the reaction route is as follows:
More preferably, when the isocyanurate compound has the structural formula III-1-2, the preparation method thereof is as follows: the alcohol and halide are subjected to substitution reaction to prepare isocyanurate compound, and the reaction route is as follows:
more preferably, when the isocyanurate compound has the structural formula III-2-1, the preparation method thereof is as follows: the alcohol and halide are subjected to substitution reaction to prepare isocyanurate compound, and the reaction route is as follows:
more preferably, when the isocyanurate compound has the structural formula III-2-2, the preparation method thereof is as follows: the alcohol and halide are subjected to substitution reaction to prepare isocyanurate compound, and the reaction route is as follows:
More preferably, when the isocyanurate compound has the structural formula III-3-1, the preparation method thereof is as follows: the alcohol and halide are subjected to substitution reaction to prepare isocyanurate compound, and the reaction route is as follows:
More preferably, when the isocyanurate compound has the structural formula III-3-2, the preparation method thereof is as follows:
The alcohol and halide are subjected to substitution reaction to prepare isocyanurate compound, and the reaction route is as follows:
the invention also discloses application of the isocyanurate compound as base oil in the field of lubricating grease.
Also disclosed is a base oil composition comprising an isocyanurate compound and a polyalphaolefin.
Preferably, the base oil composition comprises 60 to 90 parts by weight of the polyalphaolefin, 2 to 20 parts by weight of the isocyanurate compound.
For example, the polyalphaolefin may be used in an amount of 60 parts by weight, 62 parts by weight, 63 parts by weight, 70 parts by weight, 71 parts by weight, 74 parts by weight, 76 parts by weight, 78 parts by weight, 80 parts by weight, or 90 parts by weight.
For example, the isocyanurate compound may be used in an amount of 2 parts by weight, 4 parts by weight, 5 parts by weight, 7 parts by weight, 8 parts by weight, 10 parts by weight, 15 parts by weight, 16 parts by weight, or 20 parts by weight.
The isocyanurate compound is preferably used in an amount of 2 to 20 parts by weight, more preferably 4 to 20 parts by weight, still more preferably 4 to 16 parts by weight.
Preferably, the kinematic viscosity of the polyalphaolefin at 100 ℃ is 1-10 mm 2/s. As can be 1mm2/s、2mm2/s、3mm2/s、4mm2/s、5mm2/s、6mm2/s、7mm2/s、8mm2/s、9mm2/s、10mm2/s.
More preferably, the polyalphaolefin has an kinematic viscosity at 100 ℃ of 2 to 8mm 2/s. As may be 2mm2/s、3mm2/s、4mm2/s、5mm2/s、6mm2/s、7mm2/s、8mm2/s., it is further preferred that the polyalphaolefin has an kinematic viscosity at 100 ℃ of 2 to 6mm 2/s. The method for testing the kinematic viscosity comprises the following steps: the kinematic viscosity of the base oil composition was tested at 100℃using GB/T265-1988 Petroleum product kinematic viscosimetry and dynamic viscosimetry.
Preferably, the polyalphaolefin is selected from one or both of metallocene polyalphaolefins and non-metallocene polyalphaolefins. The metallocene poly alpha olefin is prepared by using a metallocene catalyst, and the preparation process of the non-metallocene poly alpha olefin uses the non-metallocene catalyst.
The non-metallocene catalyst comprises a non-metallocene inorganic-organic complex, a homogeneous Lewis acid catalyst, a heterogeneous Lewis acid catalyst, a Ziegler-Natta catalyst and a chromium-based catalyst.
The non-metallocene inorganic-organic complex is formed by ligand without cyclopentadiene structure and metal element, the metal element comprises transition metal element from IIIB group to VIII group and rare earth metal element, and ligand containing N, O, S, P hetero atoms is coordinated with the transition metal element and rare earth metal element. Such as alpha-diimine metal organic compounds, beta-diketiminate metal organic compounds, guanyl metal organic compounds, P-containing metal organic compounds, and the like.
Homogeneous Lewis acid catalysts include AlCl 3、AlBr3、TiCl3、SiCl3、BiCl3、FeCl3、BF3 or BF 3 -ROH.
The heterogeneous Lewis acid catalyst comprises the homogeneous Lewis acid catalyst and an inorganic porous substance, wherein the inorganic porous substance is selected from one or more of mesoporous carbon, carbon nano tubes, activated carbon fibers, acetylene black, carbon black, expanded graphite and graphene.
Ziegler-Natta catalysts include Et 3 Al with TiCl 4.
Chromium-based catalysts include chromium oxide, chromium halides, chromium phosphates, sulfates, nitrates, or oxalates.
Preferably, alkyl naphthalene is also included in the feed components of the base oil composition.
More preferably, the alkyl naphthalene is used in an amount of 2 to 20 parts. For example, the amount may be 2 parts, 5 parts, 10 parts, 15 parts, or 20 parts.
The invention also discloses a lubricating grease, which comprises the base oil composition and a thickening agent.
Preferably, the lubricating grease comprises the following raw material components in parts by weight:
60 to 85 parts by weight of base oil composition
5-25 Parts of thickening agent.
The base oil composition may be used in an amount of 60 parts by weight, 65 parts by weight, 70 parts by weight, 78 parts by weight, 80 parts by weight, 85 parts by weight.
The thickener may be used in an amount of 5 parts by weight, 10 parts by weight, 13.5 parts by weight, 15 parts by weight, 20 parts by weight.
Preferably, the thickener is selected from one or two of a compound or a polymer with at least 2 urea bonds and a lithium hydroxy fatty acid soap. The compound with at least 2 urea bonds comprises a bisurea compound, a compound obtained by reacting an organic amine with a diisocyanate compound. Further preferably, the diisocyanate compound is selected from one or more of phenylene diisocyanate, diphenyl diisocyanate, phenyl diisocyanate, diphenylmethane diisocyanate, cyclohexane diisocyanate, octadecane diisocyanate, decane diisocyanate and hexane diisocyanate. Further preferably, the organic amine is selected from one or both of aliphatic amine and aromatic amine. Further preferably, the organic amine has 6 to 20 carbon atoms. Further preferably, the thickener is free of free isocyanate (-NCO). Still more preferably, the thickener is polyurea powder.
Preferably, the lubricant further comprises other additives, wherein the other additives are selected from one or more of tackifier, antiwear agent, oiliness agent, antioxidant and antirust agent.
More preferably, the grease further comprises 1.5 to 13 parts by weight of the other additive.
Further preferably, the tackifier is used in an amount of 1 to 10 parts by weight in the other additive. The tackifier may be used in an amount of 1 part by weight, 3 parts by weight, 5 parts by weight, 7.3 parts by weight, 7.5 parts by weight, 9 parts by weight, 10 parts by weight.
Further preferably, the antiwear agent is used in an amount of 0.1 to 1.0 parts by weight in the other additive. For example, the amount of the components may be 0.1 part by weight, 0.2 part by weight, 0.3 part by weight, 0.4 part by weight, 0.5 part by weight, 0.6 part by weight, 0.7 part by weight, 0.8 part by weight, 0.9 part by weight, and 1.0 part by weight. The amount of the antiwear agent is too small, which affects the antiwear performance of the grease, and further preferably the amount of the antiwear agent is 0.5 to 1.0 parts by weight.
Further preferably, the amount of the oily agent in the additive is 0.1 to 0.5 parts by weight. For example, the amount of the components may be 0.1 part by weight, 0.2 part by weight, 0.3 part by weight, 0.4 part by weight, or 0.5 part by weight.
Further preferably, the antioxidant is used in an amount of 0.1 to 0.5 parts by weight in the additive. For example, the amount of the components may be 0.1 part by weight, 0.2 part by weight, 0.3 part by weight, 0.4 part by weight, or 0.5 part by weight. Too little amount of antioxidant may affect the service life of the grease, and more preferably, the amount of the antioxidant is 0.3 to 0.5 parts by weight.
Further preferably, the amount of the rust inhibitor in the additive is 0.05 to 0.2 parts by weight. For example, the amount of the components may be 0.05 parts by weight, 0.1 parts by weight, 0.15 parts by weight, or 0.2 parts by weight.
More preferably, the tackifier is a high viscosity metallocene polyalphaolefin (mPAO).
Further preferably, the high viscosity metallocene polyalphaolefin has a kinematic viscosity at 100℃of 100 to 1000mm 2/s and a viscosity index of 200 to 350. Such as a high viscosity metallocene polyalphaolefin having a kinematic viscosity of 100mm2/s、150mm2/s、300mm2/s、500mm2/s、700mm2/s、1000mm2/s., such as a high viscosity metallocene polyalphaolefin having a viscosity index of 200, 250, 300, 350.
More preferably, the antiwear agent is selected from an organophosphate or a sulfur-containing organophosphate. Further preferably, the organic phosphide is selected from one or more of tricresyl phosphate, triphenyl phosphate, triethyl phosphate, tributyl phosphate and dibutyl phosphite. Further preferably, the sulfur-containing organophosphorus compound is selected from triphenyl phosphorothioate, trialkyl phosphorothioate or amine phosphorothioate salts. Still more preferably, the antiwear agent is triphenyl thiophosphate.
More preferably, the oily agent is selected from fatty amine salts of benzotriazoles.
More preferably, the antioxidant is selected from one or both of phenolic antioxidants and aminic antioxidants. More preferably, the antioxidant is an amine antioxidant selected from one or more of diphenylamine, alkyldiphenylamine and phenyl-alpha-naphthylamine. Further preferably, the antioxidant is an alkyldiphenylamine.
More preferably, the rust inhibitor is selected from one or more of benzotriazole, alkyltriazole, benzothiazole, benzimidazole, thiadiazole, and derivatives thereof. Further preferably, the rust inhibitor is benzotriazole.
In the application, the types of the antiwear agent, the oiliness agent, the antioxidant and the antirust agent are selected as routine in the art, and can be selected by a person skilled in the art according to actual needs. The antiwear agent mainly plays a role in improving the anti-friction performance and the lubricity. The oily agent mainly plays roles of improving lubricity and preventing abrasion. The antioxidant is effective in resisting oxidation. The rust inhibitor functions to prevent corrosion of metals.
The invention also discloses a preparation method of the lubricating grease, which comprises the following steps: and uniformly mixing the raw material components of the lubricating grease, and heating to obtain the lubricating grease.
Preferably, the mixing temperature is 40-90 ℃.
Preferably, the heating temperature is 130-200deg.C, more preferably 150-180deg.C. Too low a heating temperature can affect the formation of hydrogen bonds between the thickener and the polyurea compound, and the dropping point of the grease can be reduced; if the heating temperature is too high, the oxidation degree increases, the appearance color of the grease deepens, the dropping point increases, and the shear stability decreases.
Preferably, the heating time is 1-3 hours.
Preferably, the temperature rising rate is less than or equal to 40 ℃/10min.
Preferably, the heat treatment is further followed by a grinding treatment.
More preferably, the milling temperature is 100-120 ℃.
The invention also discloses application of the lubricating grease to lubrication of bearings, sliding parts and joint parts of devices.
Preferably, the field to which the device relates includes: automotive, office equipment, work machine.
The working machine field includes construction field, agricultural machine field, mining machine field, harbor machine field, road machine field, hydraulic machine field, petroleum and natural gas exploitation machine field, electric machine field, industrial manufacturing machine field, and other special machine field (such as mechanical equipment in special fields of aerospace equipment, medical equipment, environmental protection equipment, etc.).
The invention provides an isocyanurate compound, a preparation method and application thereof, wherein the isocyanurate is used for preparing lubricating grease, and the mechanical shear stability, colloid stability, anti-friction performance, service life and anti-water-spraying performance of the lubricating grease are improved.
Detailed Description
Further advantages and effects of the present invention will become apparent to those skilled in the art from the disclosure of the present invention, which is described by the following specific examples.
Before the embodiments of the invention are explained in further detail, it is to be understood that the invention is not limited in its scope to the particular embodiments described below; it is also to be understood that the terminology used in the examples of the invention is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the invention. The test methods in the following examples, in which specific conditions are not noted, are generally conducted under conventional conditions or under conditions recommended by the respective manufacturers.
Where numerical ranges are provided in the examples, it is understood that unless otherwise stated herein, both endpoints of each numerical range and any number between the two endpoints are significant both in the numerical range. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In addition to the specific methods, devices, materials used in the embodiments, any methods, devices, and materials of the prior art similar or equivalent to those described in the embodiments of the present invention may be used to practice the present invention according to the knowledge of one skilled in the art and the description of the present invention.
Example 1
This example provides a specific isocyanurate compound III-1-1, having the structural formula
The preparation method comprises the following steps:
130.5g (0.5 mol) of tris (2-hydroxyethyl) isocyanurate was dissolved in 160mL of acetonitrile, cooled to 0℃and 33.6g (1.4 mol) of NaH as a hydrogen-withdrawing agent was added, after naturally warming up to room temperature with the heat release, 266g (1.61 mol) of 1-bromohexane was slowly added dropwise at room temperature, after completion of the dropwise addition, the temperature was raised to 75℃for reflux reaction for 16 hours, and completion of the reaction was confirmed by TLC (developing solvent petroleum ether/ethyl acetate, v/v=1:1).
The reaction solution was poured into 300mL of ice water, separated, the aqueous layer was extracted twice with ethyl acetate, the organic phases were combined, the organic phase was washed with 1 time of water and 1 time of saturated brine, dried over anhydrous magnesium sulfate, and suction-filtered to obtain a filtrate, and the filtrate was subjected to removal of the solvent by a rotary evaporator (45 ℃ C., vacuum 10 KPa) to obtain 210.3g (0.423 mol) of the product in a yield of 84.6%.
Structural characterization of the isocyanurate compound III-1-1 prepared:
IR：2965(νC-H),2917(νC-H),2854(νC-H),1682(νC＝O),1497(δC-H),1423(δC-H),1215(νC-N),1181(νC-O),1019(νC-O),799(r-(CH2)n-),696(r-CH2-CH3). Wherein n is equal to or greater than 4, r represents plane swing vibration, and delta represents deformation vibration.
1H-NMR(400MHz,CDCl3)：4.11(6H,t,J＝7.3Hz),3.48(6H,t,J＝7.3Hz),3.36(6H,t,J＝7.2Hz),1.72(6H,m,J＝7.2,5.7Hz),1.36(6H,m,J＝7.0,5.7Hz),1.28(6H,m,J＝7.0Hz),1.21(6H,quint,J＝7.0Hz),0.91(9H,t,J＝7.0Hz).
13C-NMR(400MHz,CDCl3)：149.0、71.5、70.2、48.7、31.8、29.3、25.8、22.6、14.0。
Example 2
This example provides a specific isocyanurate compound III-1-2 of the formula
The preparation process was essentially the same as in example 1, except that: the reaction was carried out using 1-bromobutane (223 g,1.63 mol) instead of 1-bromohexane at 65℃for 12h to give 210.3g (0.423 mol) of product in 84.6% yield.
Compound characterization of isocyanurate compound III-1-2:
IR：2963(νC-H),2922(νC-H),2859(νC-H),1691(νC＝O),1485(δC-H),1406(δC-H),1210(νC-N),1182(νC-O),1025(νC-O),789(r-(CH2)n-),711(r-CH2-CH3).
1H-NMR(400MHz,CDCl3)：4.06(6H,t,J＝7.3Hz),3.43(6H,t,J＝7.3Hz),3.29(6H,m,J＝6.9Hz),1.69(6H,m,J＝7.2,6.9Hz),1.42(6H,m,J＝7.1Hz),0.94(9H,t,J＝7.1Hz).
13C-NMR(400MHz,CDCl3)：149.1、71.5、70.2、48.5、31.1、19.1、14.0。
Example 3
This example provides a specific isocyanurate compound III-3-1 of the formula
The preparation method comprises the following steps:
108.5g (0.5 mol) of 1-ethyl-3, 5-bis (2-hydroxymethyl) -1,3, 5-triazine-2, 4, 6-trione are dissolved in 140mL of acetonitrile, the temperature is reduced to 0 ℃, 16.8g (0.7 mol) of hydrogen drawing agent NaH is added, 220g (1.14 mol) of bromoisooctane is slowly added dropwise at room temperature after the natural temperature rise to room temperature along with heat release, after the completion of the dropwise addition, the temperature rise to 78 ℃ and reflux reaction is carried out for 18h, and the completion of the reaction is confirmed through a TLC (developing agent is petroleum ether/ethyl acetate, v/v=1:1).
The post-treatment method was the same as in example 1. 183.4g (0.415 mol) of product were obtained in a yield of 83.1%.
Compound characterization of isocyanurate compound III-3-1:
IR：2958(νC-H),2920(νC-H),2861(νC-H),1685(νC＝O),1483(δC-H),1464(δC-H),1379(δC-H),1223(νC-N),1183(νC-O),1022(νC-O),794(r-(CH2)n-),710(r-CH2-CH3).
1H-NMR(400MHz,CDCl3)：5.38(4H,s),3.81(2H,m,J＝7.1Hz),3.66(2H,tt,J＝6.4,5.9Hz),1.58(4H,m,J＝7.5,6.4Hz),1.53(4H,m,J＝7.5,6.4Hz),1.37(4H,quint,J＝7.2Hz),1.28(4H,qt,J＝7.0,6.9Hz),1.25(4H,tt,J＝7.1,6.9Hz),1.23(3H,t,J＝7.1Hz),0.95(6H,t,J＝7.5Hz),0.87(6H,t,J＝7.0Hz).
13C-NMR(400MHz,CDCl3)：151.6、78.1、71.2、44.3、34.9、31.8、27.9、25.4、25.1、22.6、22.3、14.0、13.8、12.9、9.9、9.7.
Example 4
This example provides a specific isocyanurate compound III-3-2 of the formula
The preparation process was essentially the same as in example 3, except that: the reaction mixture was taken up in 188g (1.14 mol) of 2-bromomethyltetrahydrofuran instead of bromoisooctane and the reaction reflux temperature was 80 ℃. 154.5g (0.401 mol) of product are obtained in a yield of 80.2%.
Compound characterization of isocyanurate compound III-3-2:
IR：2959(νC-H),2921(νC-H),2858(νC-H),1678(νC＝O),1470(δC-H),1373(δC-H),1217(νC-N),1120(νC-O).
1H-NMR(400MHz,CDCl3)：5.39(4H,s),4.08(2H,ddt,J＝7.7,5.8,5.0Hz),3.92(2H,d,J＝5.0Hz),3.70～3.88(8H,m),1.76～2.12(8H,m),1.21(3H,t,J＝7.1Hz).
13C-NMR(400MHz,CDCl3)：151.9、151.5、78.1、76.5、68.7、68.2、65.7、65.0、44.5、28.1、27.4、25.7、12.9.
example 5
This example provides a specific isocyanurate compound III-2-2, having the structural formula
The preparation method comprises the following steps:
315.4g (3.5 mol) of ethylene glycol monoethyl ether is dissolved in 80mL of acetone, the temperature is reduced to 0 ℃, 84g (3.5 mol) of hydrogen drawing agent NaH is added, after the temperature is naturally raised to room temperature along with heat release, 360mL of acetone solution is slowly added dropwise at room temperature, 364.5g (0.5 mol) of tris (2, 3-dibromopropyl) isocyanurate is dissolved in the acetone solution, 3h is finished, the temperature is raised to 50 ℃ after the completion of the dripping, reflux reaction is carried out for 18h, and the completion of the reaction is confirmed through a TLC point plate (the developing agent is petroleum ether/ethyl acetate, v/v=1:1).
The post-treatment method was the same as in example 1. 311.2g (0.397 mol) of product were obtained in a yield of 79.5%.
Compound characterization of isocyanurate compound III-2-2:
IR：2960(νC-H)、2922(νC-H)、2858(νC-H)、1689(νC＝O)、1466(δC-H)、1377(δC-H)、1227(νC-N)、1112(νC-O).
1H-NMR(400MHz,CDCl3)：3.82～4.07(9H,m)、3.53～3.76(30H,m)、3.35～3.47(12H,m)、1.18～1.29(18H,m).
13C-NMR(400MHz,CDCl3)：149.6、148.9、75.5、74.9、70.6、68.4、66.7、65.7、57.9、57.3、14.2。
example 6
This example provides a specific isocyanurate compound III-2-1 of the formula
The preparation process was essentially the same as in example 5, except that: tris (2, 3-dibromopropyl) isocyanurate (364.5 g,0.5 mol) was used in place of tris (2, 3-dibromopropyl) isocyanurate, and acetone was used in an amount of 100mL to obtain 299.5g (0.382 mol) of a product in a yield of 76.4%.
Compound characterization of isocyanurate compound III-2-1:
IR：2963(νC-H)、2925(νC-H)、2856(νC-H)、1687(νC＝O)、1465(δC-H)、1376(δC-H)、1219(νC-N)、1126(νC-O).
1H-NMR(400MHz,CDCl3)：4.01(6H,d,J＝10.1Hz)、3.90(3H,tt,J＝10.1,5.3Hz)、3.53～3.65(6H,m)、3.15～3.44(42H,m)、1.91～2.05(12H,m).
13C-NMR(400MHz,CDCl3)：149.8、149.0、74.9、68.7、68.2、66.4、65.7、59.4、58.8、57.9、29.0。
Examples 7 to 22 and comparative example 1
Examples 7-22 provide specific base oil compositions and greases having the formulations shown in tables 1 and 2.
The preparation method of the base oil composition specifically comprises the following steps:
The isocyanurate compounds and polyalphaolefins prepared in examples 1 to 6 were uniformly mixed and stirred until clear and transparent, to obtain a base oil composition.
Polyalphaolefins employ mPAO10 and PAO6.
MPAO10: the mPAO represents a metallocene polyalphaolefin and the latter number represents its kinematic viscosity at 100℃in mm 2/s.
PAO6: PAO stands for non-metallocene polyalphaolefin, and the latter number stands for its kinematic viscosity at 100℃in mm 2/s.
The preparation method of the lubricating grease specifically comprises the following steps:
And fully and uniformly stirring the base oil composition, the thickening agent and other additives at 60 ℃, gradually heating the system to 160 ℃ at a heating rate of 25 ℃/10min for puffing, keeping the system temperature unchanged in the puffing process, starting timing when the system temperature is raised to a set puffing temperature, stopping heating after puffing for 2 hours, starting cooling, and transferring to a three-roller grinder for grinding for three times when the system is cooled to 110 ℃ to obtain the corresponding lubricating grease.
The adhesion promoter is mPAO150, which represents a metallocene polyalphaolefin and the latter number represents its kinematic viscosity at 100℃in mm 2/s.
The thickening agent adopts polyurea powder which is purchased from a new photo-luminescent material (Dongguan) limited company and has no free isocyanato.
The antiwear agent was T309 (triphenyl thiophosphate) available from the lubricant additives company, contai, inc.
The oily agent was T406 (benzotriazole fatty acid amine salt), available from kun-chou lubrication technologies, inc.
The antioxidant was T534 (alkyl diphenylamine), available from St.John's chemical Co., ltd.
The rust inhibitor was selected from T551 (benzotriazole derivative), available from Panhua chemical (Shanghai) Co., ltd.
Table 1 shows the units in parts by weight
TABLE 2
The greases prepared in examples 7 to 22 and comparative example 1, commercially available greases were subjected to the following performance tests: friction resistance, mechanical shear stability, drip point, copper sheet corrosiveness, colloid stability, water spray resistance and service life. The test results are shown in tables 3 and 4.
The test methods or criteria are as follows:
Anti-friction properties: the average plaque diameter of a grease sample was determined using ASTM D2266 standard test method for anti-wear properties of greases (four ball machine method); the four-ball test conditions are as follows: load: 392N (40 kgf); spindle rotational speed: 1200r/min; test time: 60min; test temperature: 75 ℃.
And after the test is finished, measuring the abrasion spot diameter of the lower steel ball, wherein the smaller the abrasion spot diameter is, the better the abrasion resistance of the sample is represented, and taking the average value of the abrasion spot diameters of the 3 lower steel balls to evaluate the abrasion resistance of the lubricating grease sample.
Mechanical shear stability: the unworked cone penetration of the grease, the cone penetration after 60 reciprocations and the cone penetration after 10 ten thousand reciprocations were measured at 25℃using GB/T269-1991 method for measuring cone penetration of grease and petrolatum, and the cone penetration difference was obtained by subtracting the cone penetration after 60 working from the cone penetration after 10 ten thousand working.
Drop point: the drop point of the grease was determined using GB/T4929-1985 "drop Point determination of grease".
Corrosiveness of copper sheet: the corrosiveness of the grease to the copper sheet was determined using GB 7326-1987 method for corrosion test of copper sheet of grease.
Colloidal stability: the steel mesh oil percentage (w/w,%) of the lubricating grease is tested by adopting NB/SH/T0324-2010 Cone network method for measuring the oil content of the lubricating grease steel mesh, and the test conditions are as follows: 100 ℃ for 30h.
Water shower resistance: the water spray resistance of the lubricating grease is measured by adopting a method of a standard SH/T0109-2004 method for testing the water spray resistance of the lubricating grease, firstly, 4g of lubricating grease sample is filled in a ball bearing, water is continuously sprayed to the bearing filled with the lubricating grease for 1 hour at a certain temperature (79 ℃) and a certain flow rate (5 mL/s), and the water spray loss of the lubricating grease is calculated, so that the water spray resistance of the lubricating grease is evaluated.
Service life is as follows: the service life of the grease was measured by reference to ASTM D3336, test speed 10000r/min, test temperature 300℃F (148.9 ℃), and the time to failure of the grease was recorded. Judging the failure of the lubricating grease: grease is diluted and lost, dried, hardened, coked or forms sticky carbon deposit, and the like, so that the lubrication function cannot be normally exerted.
Test cycle 21 half hours of operation at 149 ℃ (300°f) and 22 hours of shutdown without heating.
TABLE 3 Table 3
TABLE 4 Table 4
As can be seen from tables 1 to 4:
When the consumption of the isocyanurate compound is higher, the prepared lubricating grease is higher in dropping point, lower in cone penetration difference value, lower in steel mesh oil distribution ratio and lower in weight loss ratio of water drenching, which indicates that the isocyanurate compound is favorable for improving the dropping point, mechanical shear stability, colloid stability and water drenching resistance of the lubricating grease when being used in the lubricating grease.
The addition of an appropriate amount of isocyanurate compound is beneficial to prolonging the service life, reducing the abrasion diameter and improving the anti-friction performance, but the anti-friction performance and the service life of the lubricating grease are also reduced after the usage amount of the isocyanurate compound is excessively high (more than 8 parts by weight), and the lubricating grease is possibly related to the fact that the isocyanurate compound has higher polarity and is easy to adsorb polar auxiliary agents, so that the whole performance is reduced due to the influence of the polar auxiliary agents.
The above embodiments are merely illustrative of the principles of the present invention and its effectiveness, and are not intended to limit the invention. Modifications and variations may be made to the above-described embodiments by those skilled in the art without departing from the spirit and scope of the invention. Accordingly, it is intended that all equivalent modifications and variations of the invention be covered by the claims, which are within the ordinary skill of the art, be within the spirit and scope of the present disclosure.
Claims (13)
1. An isocyanurate compound, characterized in that the isocyanurate compound has a structural formula as shown in formula III:
Wherein R 1、R3 is independently selected from an ether group with 1-30 carbon atoms and/or an alkyl group, and R 2 is selected from an ether group with 1-30 carbon atoms.
2. The isocyanurate compound of claim 1, wherein the isocyanurate compound comprises a compound of formula III-1, a compound of formula III-2, a compound of formula III-3, a compound of formula III-4; the structural formulas of the compound of the formula III-1, the compound of the formula III-2, the compound of the formula III-3 and the compound of the formula III-4 are shown as follows:
Wherein R '1、R'2 and R' 3 are independently selected from ether groups and/or alkyl groups with 1-10 carbon atoms, and R 0 is selected from ether groups and/or alkyl groups with 1-20 carbon atoms.
3. The isocyanurate compound of claim 2, comprising one or more of the following characteristics: in the compound of formula III-1, R' 1 has the structural formula:
In the compound of formula III-2, R' 1 has the structural formula:
in the compound of formula III-3, R' 1 has the structural formula:
In the compound of formula III-1, R' 2 has the structural formula:
in the compound of formula III-2, R' 2 has the structural formula:
in the compound of formula III-3, R' 2 has the structural formula:
in the compound of formula III-1, R' 3 has the structural formula:
in the compound of formula III-2, R' 3 has the structural formula:
in the compound of formula III-3, R' 3 has the structural formula:
In the compound of formula III-1, R' 0 has the structural formula:
in the compound of formula III-2, R' 0 has the structural formula:
in the compound of formula III-3, R' 0 has the structural formula:
4. The isocyanurate compound of claim 1, comprising one or more of the following characteristics: the compounds of formula III-1 include:
The compounds of formula III-2 include:
the compounds of formula III-3 include:
5. A process for producing the isocyanurate compound according to any one of claims 1 to 4, comprising the steps of: the alcohol and the halide undergo substitution reaction to prepare the isocyanurate compound.
6. The method of manufacturing according to claim 5, comprising one or more of the following features:
The halide is selected from chloride, bromide or iodide;
The reaction system comprises a hydrogen drawing agent, wherein the hydrogen drawing agent is one or more selected from diisopropyl amino lithium, n-butyl lithium, tert-butyl lithium, sodium hydride, potassium carbonate, sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, sodium tert-butoxide and potassium tert-butoxide;
The reaction system comprises a reaction medium, wherein the reaction medium is selected from one or more of N, N-dimethylformamide, dimethyl sulfoxide, acetonitrile and acetone;
the reaction temperature is more than or equal to 40 ℃;
the reaction process also includes a post-treatment step that includes separation and removal of impurities.
7. Use of the isocyanurate compound according to any one of claims 1 to 4 as a base oil in the field of greases.
8. A base oil composition comprising the isocyanurate compound of any one of claims 1 to 4 and a polyalphaolefin.
9. The base oil composition of claim 8, wherein the base oil composition comprises 60 to 90 parts by weight of the polyalphaolefin, 2 to 25 parts by weight of the isocyanurate compound.
10. Grease comprising a base oil composition according to any one of claims 8 to 9 and a thickener.
11. The grease of claim 10, comprising one or more of the following features:
a) The thickening agent is one or two selected from a compound or a polymer with at least 2 urea bonds and a hydroxy fatty acid lithium soap;
b) The oil-based antirust paint also contains other additives, wherein the other additives are selected from one or more of tackifier, antiwear agent, oiliness agent, antioxidant and antirust agent;
c) The lubricating grease comprises the following raw material components in parts by weight:
60 to 85 parts by weight of base oil composition
5-25 Parts of thickening agent.
12. The grease of claim 11, comprising one or both of the following features:
a) The tackifier is high-viscosity metallocene poly alpha-olefin;
b) The using amount of the other additives in the lubricating grease is 1.5-13 parts by weight; preferably, in the other additives, the tackifier is used in an amount of 1 to 10 parts by weight.
13. Use of a grease according to any one of claims 10 to 12 for lubricating bearings, sliding parts, joints of a device.
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| JPH02132190A (en) * | 1988-07-15 | 1990-05-21 | Nippon Steel Corp | Lubricating oil |
| CN1583985A (en) * | 2003-08-19 | 2005-02-23 | 西安近代化学研究所 | Lubricant for tetrafluoroethane refrigerant |
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| US20120231297A1 (en) * | 2011-03-07 | 2012-09-13 | Fujifilm Corporation | Lubricant composition, fluorine-based compound, and use thereof |
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| CN108884082A (en) * | 2016-04-07 | 2018-11-23 | 日产化学株式会社 | Single glycidyl isocyanurate compound and its manufacturing method |
| CN111943896A (en) * | 2020-07-24 | 2020-11-17 | 深圳市优宝新材料科技有限公司 | High-speed bearing lubricating grease with good oxidation resistance |
-
2024
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3637557A (en) * | 1969-09-23 | 1972-01-25 | Allied Chem | Esters of tris(polyalkyleneoxy) isocyanurates |
| JPS5030079B1 (en) * | 1970-12-21 | 1975-09-29 | ||
| JPS4840792A (en) * | 1971-10-08 | 1973-06-15 | ||
| EP0010452A1 (en) * | 1978-10-25 | 1980-04-30 | Olin Corporation | Tris-(polyalkoxyalkylated) isocyanurate compounds and their use as functional fluids |
| JPH02132190A (en) * | 1988-07-15 | 1990-05-21 | Nippon Steel Corp | Lubricating oil |
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| CN108884082A (en) * | 2016-04-07 | 2018-11-23 | 日产化学株式会社 | Single glycidyl isocyanurate compound and its manufacturing method |
| CN111943896A (en) * | 2020-07-24 | 2020-11-17 | 深圳市优宝新材料科技有限公司 | High-speed bearing lubricating grease with good oxidation resistance |
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