CN111072702B - 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 - Google Patents
一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 Download PDFInfo
- Publication number
- CN111072702B CN111072702B CN201811212642.2A CN201811212642A CN111072702B CN 111072702 B CN111072702 B CN 111072702B CN 201811212642 A CN201811212642 A CN 201811212642A CN 111072702 B CN111072702 B CN 111072702B
- Authority
- CN
- China
- Prior art keywords
- grease
- silole
- base oil
- integer
- hydrogen
- 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.)
- Active
Links
- 239000004519 grease Substances 0.000 title claims abstract description 62
- 150000003967 siloles Chemical class 0.000 title claims abstract description 39
- 230000001050 lubricating effect Effects 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims description 55
- 239000002199 base oil Substances 0.000 claims description 53
- -1 silole compound Chemical class 0.000 claims description 41
- 239000002562 thickening agent Substances 0.000 claims description 32
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 21
- 238000010438 heat treatment Methods 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 15
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 15
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 14
- 229910052782 aluminium Inorganic materials 0.000 claims description 12
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 11
- 229910052744 lithium Inorganic materials 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 229950000688 phenothiazine Drugs 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 10
- 238000007670 refining Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 239000000194 fatty acid Substances 0.000 claims description 9
- 229920002396 Polyurea Polymers 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 238000000227 grinding Methods 0.000 claims description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- 229910001507 metal halide Inorganic materials 0.000 claims description 6
- 150000005309 metal halides Chemical class 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000010687 lubricating oil Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 239000007850 fluorescent dye Substances 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 238000003384 imaging method Methods 0.000 claims 1
- 238000005424 photoluminescence Methods 0.000 abstract description 4
- 230000003647 oxidation Effects 0.000 abstract description 3
- 238000007254 oxidation reaction Methods 0.000 abstract description 3
- 235000013305 food Nutrition 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 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 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 239000000344 soap Substances 0.000 description 7
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 6
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 6
- 235000021355 Stearic acid Nutrition 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 6
- 239000008117 stearic acid Substances 0.000 description 6
- 239000013638 trimer Substances 0.000 description 6
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 5
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 4
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 4
- RXTTTXHDUDEPEE-UHFFFAOYSA-N 2-iodo-10h-phenothiazine Chemical compound C1=CC=C2NC3=CC(I)=CC=C3SC2=C1 RXTTTXHDUDEPEE-UHFFFAOYSA-N 0.000 description 3
- DXFHSYZYJQBTSI-UHFFFAOYSA-N 2-pentaphen-1-yl-1H-silole Chemical compound C1(=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12)C1=CC=C[SiH2]1 DXFHSYZYJQBTSI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- FPUIBHWOSCSYHI-UHFFFAOYSA-N 2-benzo[a]anthracen-1-yl-1H-silole Chemical compound C1(=CC=CC2=CC=C3C=C4C=CC=CC4=CC3=C12)C1=CC=C[SiH2]1 FPUIBHWOSCSYHI-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- PKVRJCUKSNFIBN-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 PKVRJCUKSNFIBN-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 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
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- YGRVCNYIEKLRED-UHFFFAOYSA-N 4,4-diphenylbutylphosphane Chemical compound C=1C=CC=CC=1C(CCCP)C1=CC=CC=C1 YGRVCNYIEKLRED-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910021575 Iron(II) bromide Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000010425 asbestos Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 238000012984 biological imaging Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006229 carbon black Chemical group 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- GNVFTBURMUIKJD-UHFFFAOYSA-L dichlororhodium;triphenylphosphane Chemical compound Cl[Rh]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 GNVFTBURMUIKJD-UHFFFAOYSA-L 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229940046149 ferrous bromide Drugs 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 229940076136 ferrous iodide Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- HEJPGFRXUXOTGM-UHFFFAOYSA-K iron(3+);triiodide Chemical compound [Fe+3].[I-].[I-].[I-] HEJPGFRXUXOTGM-UHFFFAOYSA-K 0.000 description 1
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
- BQZGVMWPHXIKEQ-UHFFFAOYSA-L iron(ii) iodide Chemical compound [Fe+2].[I-].[I-] BQZGVMWPHXIKEQ-UHFFFAOYSA-L 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- IGTVAJJAPJKARK-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 IGTVAJJAPJKARK-UHFFFAOYSA-N 0.000 description 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- GZKMGAXTHYGXEO-UHFFFAOYSA-M ruthenium(1+);triphenylphosphane;chloride Chemical compound [Ru]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 GZKMGAXTHYGXEO-UHFFFAOYSA-M 0.000 description 1
- PMKLSZDLLHGDMO-UHFFFAOYSA-L ruthenium(2+);triphenylphosphane;dichloride Chemical compound Cl[Ru]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 PMKLSZDLLHGDMO-UHFFFAOYSA-L 0.000 description 1
- BFPFOLJFUVTHEP-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BFPFOLJFUVTHEP-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- FEQPHYCEZKWPNE-UHFFFAOYSA-K trichlororhodium;triphenylphosphane Chemical compound Cl[Rh](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FEQPHYCEZKWPNE-UHFFFAOYSA-K 0.000 description 1
- CMTKJYPJPSONIT-UHFFFAOYSA-K trichlororuthenium;triphenylphosphane Chemical compound Cl[Ru](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMTKJYPJPSONIT-UHFFFAOYSA-K 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229960001939 zinc chloride Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
- C10M139/04—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00 having a silicon-to-carbon bond, e.g. silanes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
-
- 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
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
-
- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/124—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers thereof
- C10M2207/1245—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers thereof used as thickening agent
-
- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
-
- 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
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- 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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Lubricants (AREA)
Abstract
本发明提供了一种噻咯衍生物及其制备方法、用途和包含该噻咯衍生物的光致发光润滑脂。本发明的噻咯衍生物，其结构如通式(I)所示：
Description
技术领域
本发明涉及一种噻咯衍生物，特别涉及一种具有发光性能的噻咯衍生物。
背景技术
传统有机发色团通常在低浓度下具有较强发光，而在高浓度或固态下发光微弱甚至不发光，呈现聚集荧光猝灭效应。这是由于在聚集态下，分子间强烈的相互作用导致激发态非辐射衰减过程增强，荧光量子产率显著降低。在实际应用过程中，聚集荧光猝灭效应在很大程度上限制了有机发光材料的实际应用。近年来的研究发现，有些化合物显现出与传统有机发光化合物相反的性质，不仅没有聚集荧光猝灭效应，反而呈现聚集诱导发光(AIE)性质，聚集诱导发光化合物的出现为有机发光材料在固态或高浓度下的应用提供了新的解决方案。
润滑脂是将稠化剂分散在液体润滑剂内制备的固体至半流体产品，具有润滑、保护和密封的作用，在工业机械、农业机械、交通运输行业、航空航天业、电子信息业和各类军事装备中起到至关重要的作用。
在一些黑暗的工况条件下，润滑脂的监测存在着很大的难度。目前鲜见发光润滑脂的相关报道。
发明内容
本发明提供了一种噻咯衍生物及其制备方法、用途和包含该噻咯衍生物的光致发光润滑脂。
本发明的噻咯衍生物，其结构如通式(I)所示：
在通式(I)中，各个R各自独立地选自氢、C1-6直链或支链烷基；x为0～5之间的整数；y为0～3之间的整数；z为0～4之间的整数；R1选自氢、C1-6直链或支链烷基、C6-10芳基。
根据本发明，优选地，在通式(I)中，各个R选自氢、C1-4直链或支链烷基；x为0～3之间的整数；y为0、1或2；z为0、1或2；R1选自氢、C1-4直链或支链烷基、苯基。
根据本发明，可以举出的所述噻咯衍生物包括如下化合物中的一种或多种：
本发明所述的噻咯衍生物的制备方法，包括使通式(II)所示的噻咯化合物和通式(III)所示的吩噻嗪化合物发生反应的步骤，
在通式(II)、(III)中，各个R各自独立地选自氢、C1-6直链或支链烷基；x为0～5之间的整数；y为0～3之间的整数；z为0～4之间的整数；R1选自氢、C1-6直链或支链烷基、C6-10芳基；X选自F、Cl、Br、I、OH。
根据本发明，优选地，在通式(I)中，各个R选自氢、C1-4直链或支链烷基；x为0～3之间的整数；y为0、1或2；z为0、1或2；R1选自氢、C1-4直链或支链烷基、苯基；X选自Cl、Br、I、OH。
根据本发明，优选地，通式(II)所示的噻咯化合物包括：
根据本发明，优选地，通式(III)所示的吩噻嗪化合物包括：
根据本发明的制备方法，优选地，在所述反应中，通式(II)所示的噻咯化合物和通式(III)所示的吩噻嗪化合物之间的摩尔比优选为1：0.5～5，最优选1：0.8～1.2。
根据本发明的制备方法，优选地，所述反应的温度为0～50℃，优选15～35℃。
根据本发明的制备方法，优选地，所述反应的时间为6～96h，优选12～72h。
根据本发明，在所述反应中优选加入催化剂。所述催化剂优选金属膦配合物、金属卤化物和烃基膦化合物中的一种或多种，更优选金属膦配合物、金属卤化物和烃基膦化合物的混合物，三者之间的摩尔比优选为1：0.1～10：0.1～10，更优选为1：0.2～5：0.2～5。
根据本发明，优选地，所述金属膦配合物的结构为
其中M为Pd、Ru或Rh，L选自PPh3、Ph、F、Cl、Br、I。所述金属膦配合物可以选用四(三苯基膦)钯、三(三苯基膦)氯化钯、二(三苯基膦)二氯化钯、(三苯基膦)三氯化钯、四(三苯基膦)钌、三(三苯基膦)氯化钌、二(三苯基膦)二氯化钌、(三苯基膦)三氯化钌、四(三苯基膦)铑、三(三苯基膦)氯化铑、二(三苯基膦)二氯化铑和(三苯基膦)三氯化铑中的一种或多种，优选四(三苯基膦)钯、三(三苯基膦)氯化钯、二(三苯基膦)二氯化钯和(三苯基膦)三氯化钯中的一种或多种。
根据本发明，优选地，所述金属卤化物可以选用铜卤化物、铁卤化物和锌卤化物中的一种或多种，例如可以选用氯化铜、氯化亚铜、溴化铜、溴化亚铜、碘化铜、碘化亚铜、氯化铁、氯化亚铁、溴化铁、溴化亚铁、碘化铁、碘化亚铁、氯化锌、氯化亚锌、溴化锌、溴化亚锌、碘化锌和碘化亚锌中的一种或多种，更优选氯化铜、氯化亚铜、溴化铜、溴化亚铜、碘化铜和碘化亚铜中的一种或多种。
根据本发明，优选地，所述烃基膦化合物的结构为
其中的各个R各自独立地选自C6～C10的芳基和C1～C6的直链或支链烷基，其中至少一个R为C6～C10的芳基。所述C6～C10的芳基可以选自苯基、萘基；所述C1～C6的直链或支链烷基可以选自甲基、乙基、丙基、异丙基、丁基、异丁基、戊基、异戊基、己基或异己基。所述烃基膦化合物可以选用三苯基膦、二苯基丁基膦。
根据本发明，所述催化剂的加入量优选为式(II)所示的噻咯化合物质量的1％～20％。
根据本发明的制备方法，优选地，在所述反应中加入溶剂。所述溶剂优选C1～C10的有机胺、呋喃，例如可以选用甲胺、二甲胺、三甲胺、乙胺、二乙胺、三乙胺、丙胺、二丙胺、三丙胺、四氢呋喃，最优选C1～C10的有机胺与呋喃的混合溶剂，二者之间的体积比优选为1：0.1～10。所述溶剂在反应结束后可以通过本领域所公知的方法除去，并没有特别的限定，去除方法包括蒸馏、蒸发、柱层析的方法。优选地，采用柱层析方法分离提纯本发明的噻咯衍生物，可以使用二氯甲烷/石油醚的混合溶剂作为洗脱剂，所述二氯甲烷与石油醚的体积比优选为1：0.5～5。
本发明所述的噻咯衍生物具有优异的光致发光性能，能够在紫外光照射下发出黄色荧光，可以应用于发光部件及装置、荧光探针、生物成像、润滑油和润滑脂中。
本发明还提出了一种润滑脂，包括上述的噻咯衍生物、稠化剂和润滑基础油。所述噻咯衍生物占润滑脂总质量的0.01％～5.0％，优选0.1％～1.0％；所述稠化剂占润滑脂总质量的5％～30％，优选10％～20％；所述润滑基础油构成润滑脂的主要成分。
所述的稠化剂包括聚脲稠化剂、锂基稠化剂、复合锂基稠化剂、钙基稠化剂和复合铝基稠化剂中的一种或多种，优选聚脲稠化剂、锂基稠化剂、复合锂基稠化剂、复合铝基稠化剂，最优选锂基稠化剂。
所述的基础油可以是矿物油、植物油和合成油中的一种或多种，优选矿物油、合成油。
本发明的润滑脂具有优异的光致发光性能、抗氧性能。
本发明润滑脂的制备方法，包括：将润滑基础油、稠化剂、噻咯衍生物混合炼制，研磨成脂。所述炼制操作的温度为160～240℃，优选180～220℃；所述炼制操作的时间为10～240min，优选20～60min。可以将全部的润滑基础油、噻咯衍生物、稠化剂一起混合炼制，也可以将部分润滑基础油、部分噻咯衍生物与稠化剂混合炼制后，再与余下的润滑基础油、余下的噻咯衍生物混合。
所述稠化剂可以为皂基稠化剂，也可以为非皂基稠化剂。所述皂基稠化剂优选金属皂，可以为单一金属皂，也可以为复合金属皂，所述金属可以为锂、钠、钙、铝、锌、钾、钡、铅、锰中的一种或多种。所述非皂基脂稠化剂优选石墨、炭黑、石棉、聚脲基、膨润土、有机黏土中的一种或多种。
本发明的润滑脂优选聚脲润滑脂、锂基润滑脂和复合铝基润滑脂。
本发明的聚脲润滑脂的制备方法，包括：将部分润滑基础油、前面所述的噻咯衍生物、胺、异氰酸酯混合，在65～95℃反应10-60min，反应完全后继续升温至190～220℃进行高温炼制，然后加入剩余的基础油冷却至60～120℃，研磨成脂。所述胺为C2～C20烷基胺和/或C6～C20芳香胺，例如可以是十八胺、环己胺、苯胺中的一种或多种；所述异氰酸酯为C2～C20的异氰酸酯，可以是甲苯二异氰酸酯(TDI)、4,4’-二苯基甲烷二异氰酸酯(MDI)中的一种或多种。
本发明的锂基润滑脂的制备方法，包括：将部分润滑基础油与脂肪酸在反应釜中混合加热，升温至40～90℃，加入前面所述的噻咯衍生物、氢氧化锂的水溶液，加热除水后继续升温至190～220℃进行高温炼制炼制，加入剩余的润滑基础油冷却至60～120℃，研磨成脂。所述脂肪酸为C12～C20脂肪酸和/或C12～C20羟基脂肪酸，可以是月桂酸、棕榈酸、硬脂酸和12-羟基硬脂酸中的一种或多种。
本发明的复合铝基润滑脂的制备方法，包括：将部分基础油、脂肪酸与小分子酸在反应釜中混合加热，升温至40～90℃，加入前面所述的噻咯衍生物，将另一部分润滑基础油与醇铝化合物混合加热升温至40～100℃，待醇铝化合物全部溶解后加入到反应釜中，继续升温至190～220℃进行高温炼制，加入剩余的润滑基础油冷却至60～120℃，研磨成脂。所述脂肪酸为C12～C20脂肪酸和/或C12～C20羟基脂肪酸，可以是月桂酸、棕榈酸、硬脂酸、12-羟基硬脂酸中的一种或多种；所述小分子酸为C2～C11的有机酸，可以是醋酸、丙酸、乙二酸、己二酸、壬二酸、癸二酸、对苯二甲酸中的一种或多种；所述醇铝化合物优选选自异丙醇铝、异丙醇铝二聚体、异丙醇铝三聚体。
根据本发明的润滑脂制备方法，优选地，预先将噻咯衍生物溶解在溶剂中。所述溶剂优选芳烃溶剂，例如可以选用苯、甲苯、二甲苯，所述溶剂的重量为噻咯衍生物重量的0.5～100倍(优选1～20倍)。
本发明的润滑脂具有优异的光致发光性能和抗氧化性能，可以应用于电器工业、冶金工业、食品工业、造纸工业、汽车工业、飞机工业的相关机械设备。
具体实施方式
所使用的主要原料如下：
1-炔基-1,2,3,4,5-五苯基噻咯、1-甲基-1-炔基-2,3,4,5-四苯基噻咯、2-碘酚噻嗪、碘化亚铜、三苯基膦、四三苯基膦钯、十八胺、MDI、12-羟基硬脂酸、硬脂酸、苯甲酸、一水合氢氧化锂、异丙醇铝三聚体、四氢呋喃、三乙胺、二氯甲烷、石油醚等化学试剂来自于百灵威试剂公司、伊诺凯试剂公司或西格玛试剂公司，分析纯；PAO10基础油来自于埃克森美孚公司。
实施例1
在100mLSchlenk反应瓶中加入487mg(1mmol)1-炔基-1,2,3,4,5-五苯基噻咯，390mg(1.2mmol)2-碘吩噻嗪，19mg(0.1mmol)碘化亚铜，26mg(0.1mmol)三苯基膦，在氮气保护下加入23mg(0.02mmol)四三苯基膦钯，30mL四氢呋喃/三乙胺(2/1,v/v)，室温下反应48小时。反应结束后，过滤并将滤液旋干，以二氯甲烷/石油醚(1/2,v/v)混合溶剂作为洗脱剂用柱层析法对产物进行分离提纯，得到黄色固体产物490mg，产率为72％。产物核磁结果为：1HNMR(400MHz,CDCl3),δ(TMS,ppm):7.74(m,2H),7.36(m,3H),7.20–6.82(m,27H)；MS(MALDI-TOF):m/z calcd:683.2[M]+,found:683.2。
实施例1的反应式如下所示：
在100mLSchlenk反应瓶中加入425mg(1mmol)1-甲基-1-炔基-2,3,4,5-四苯基噻咯，390mg(1.2mmol)2-碘吩噻嗪，19mg(0.1mmol)碘化亚铜，26mg(0.1mmol)三苯基膦，在氮气保护下加入23mg(0.02mmol)四三苯基膦钯，30mL四氢呋喃/三乙胺(2/1,v/v)，室温下反应48小时。反应结束后，过滤并将滤液旋干，以二氯甲烷/石油醚(1/2,v/v)混合溶剂作为洗脱剂用柱层析法对产物进行分离提纯，得到黄色固体产物460mg，产率为74％。产物核磁结果为：1H NMR(400MHz,CDCl3),δ(TMS,ppm):7.18–6.84(m,27H),0.24(s,3H)；MS(MALDI-TOF):m/z calcd:621.2[M]+,found:621.2。
实施例2的反应式如下所示：
将145克的PAO10基础油与44.39克十八胺在反应釜中混合加热到60℃，将2.5克由实施例1制得的1-(2-炔基吩噻嗪)-1,2,3,4,5-五苯基噻咯溶于25克甲苯加入到反应釜中，将145克的PAO10基础油与20.61克MDI混合加热到60℃，待MDI全部溶解后加入到反应釜中，升温至80℃反应30min，继续升温至210℃，再加入145克的PAO10基础油冷却至100℃左右研磨成脂。
实施例4
将145克的PAO10基础油与44.39克十八胺在反应釜中混合加热到60℃，将2.5克由实施例2制得的1-甲基-1-(2-炔基吩噻嗪)-2,3,4,5-四苯基噻咯溶于25克甲苯加入到反应釜中，将145克的PAO10基础油与20.61克MDI混合加热到60℃，待MDI全部溶解后加入到反应釜中，升温至80℃反应30min，继续升温至210℃，再加入145克的PAO10基础油冷却至100℃左右研磨成脂。
实施例5
将145克的PAO10基础油与44.39克十八胺在反应釜中混合加热到60℃，将145克的PAO10基础油与20.61克MDI混合加热到60℃，待MDI全部溶解后加入到反应釜中，升温至80℃反应30min，继续升温至210℃，再加入145克的PAO10基础油冷却至100℃左右加入2.5克由实施例1制得的1-(2-炔基吩噻嗪)-1,2,3,4,5-五苯基噻咯，研磨成脂。
对比例1
将145克的PAO10基础油与44.39克十八胺在反应釜中混合加热到60℃，将145克的PAO10基础油与20.61克MDI混合加热到60℃，待MDI全部溶解后加入到反应釜中，升温至80℃反应30min，继续升温至210℃，再加入145克的PAO10基础油冷却至100℃左右研磨成脂。
对实施例3、实施例4、实施例5、对比例1的润滑脂进行了性能评定，评定方法为GB/T 3498、GB/T 269、SH/T 0719、SH/T 0325、SH/T 0324，评定结果见表1。
表1 评定结果
实施例6
将300克的PAO10基础油与39.21克12-羟基硬脂酸在反应釜中混合加热到85℃，将2.5克由实施例1制得的1-(2-炔基吩噻嗪)-1,2,3,4,5-五苯基噻咯溶于25克甲苯加入到反应釜中，将6.06克的一水合氢氧化锂与40克蒸馏水混合加热到95℃，待氢氧化锂全部溶解后加入到反应釜中，加热除水后继续升温至210℃，再加入160克的PAO10基础油，冷却后研磨成脂。
实施例7
将300克的PAO10基础油与39.21克12-羟基硬脂酸在反应釜中混合加热到85℃，将2.5克由实施例2制得的1-甲基-1-(2-炔基吩噻嗪)-2,3,4,5-四苯基噻咯溶于25克甲苯加入到反应釜中，将6.06克的一水合氢氧化锂与40克蒸馏水混合加热到95℃，待氢氧化锂全部溶解后加入到反应釜中，加热除水后继续升温至210℃，再加入160克的PAO10基础油，冷却后研磨成脂。
对比例2
将300克的PAO10基础油与39.21克12-羟基硬脂酸在反应釜中混合加热到85℃，将6.06克的一水合氢氧化锂与40克蒸馏水混合加热到95℃，待氢氧化锂全部溶解后加入到反应釜中，加热除水后继续升温至210℃，再加入160克的PAO10基础油，冷却后研磨成脂。
对实施例6、实施例7、对比例2的润滑脂进行了性能评定，评定方法同前，评定结果见表2。
表2 评定结果
实施例8
将200克的PAO10基础油、32.5克硬脂酸与14克苯甲酸在反应釜中混合加热到90℃，将2.5克由实施例1制得的1-(2-炔基吩噻嗪)-1,2,3,4,5-五苯基噻咯溶于25克甲苯加入到反应釜中，将100克的PAO10基础油与32克异丙醇铝三聚体混合加热，待异丙醇铝三聚体全部溶解后加入到反应釜中，继续升温至210℃反应30分钟，再加入150克的PAO10基础油，冷却后研磨成脂。
实施例9
将200克的PAO10基础油、32.5克硬脂酸与14克苯甲酸在反应釜中混合加热到90℃，将2.5克由实施例2制得的1-甲基-1-(2-炔基吩噻嗪)-2,3,4,5-四苯基噻咯溶于25克甲苯加入到反应釜中，将100克的PAO10基础油与32克异丙醇铝三聚体混合加热，待异丙醇铝三聚体全部溶解后加入到反应釜中，继续升温至210℃反应30分钟，再加入150克的PAO10基础油，冷却后研磨成脂。
对比例3
将200克的PAO10基础油、32.5克硬脂酸与14克苯甲酸在反应釜中混合加热到90℃，将100克的PAO10基础油与32克异丙醇铝三聚体混合加热，待异丙醇铝三聚体全部溶解后加入到反应釜中，继续升温至210℃反应30分钟，再加入150克的PAO10基础油，冷却后研磨成脂。对实施例8、实施例9、对比例3的润滑脂进行了性能评定，评定方法同前，评定结果见表3。
表3 评定结果
Claims (19)
1.一种噻咯衍生物，其结构如通式(I)所示：
在通式(I)中，各个R各自独立地选自氢、C1-6直链或支链烷基；x为0～5之间的整数；y为0～3之间的整数；z为0～4之间的整数；R1选自氢、C1-6直链或支链烷基、C6-10芳基。
2.按照权利要求1所述的噻咯衍生物，其特征在于，在通式(I)中，各个R选自氢、C1-4直链或支链烷基；x为0～3之间的整数；y为0、1或2；z为0、1或2；R1选自氢、C1-4直链或支链烷基、苯基。
3.按照权利要求1所述的噻咯衍生物，其特征在于，所述噻咯衍生物为如下化合物中的一种或多种：
4.一种噻咯衍生物的制备方法，包括使通式(II)所示的噻咯化合物和通式(III)所示的吩噻嗪化合物发生反应的步骤，
在通式(II)、(III)中，各个R各自独立地选自氢、C1-6直链或支链烷基；x为0～5之间的整数；y为0～3之间的整数；z为0～4之间的整数；R1选自氢、C1-6直链或支链烷基、C6-10芳基；X选自F、Cl、Br、I、OH。
5.按照权利要求4所述的方法，其特征在于，在通式(I)中，各个R选自氢、C1-4直链或支链烷基；x为0～3之间的整数；y为0、1或2；z为0、1或2；R1选自氢、C1-4直链或支链烷基、苯基；X选自Cl、Br、I、OH。
6.按照权利要求4所述的方法，其特征在于，通式(II)所示的噻咯化合物为如下化合物中的一种：
通式(III)所示的吩噻嗪化合物为如下化合物中的一种：
7.按照权利要求4所述的方法，其特征在于，在所述反应中，通式(II)所示的噻咯化合物和通式(III)所示的吩噻嗪化合物之间的摩尔比为1：0.5～5；所述反应的温度为0～50℃。
8.按照权利要求4所述的方法，其特征在于，在所述反应中加入催化剂，所述催化剂为金属膦配合物、金属卤化物和烃基膦化合物中的一种或多种。
9.按照权利要求8所述的方法，其特征在于，所述催化剂为金属膦配合物、金属卤化物和烃基膦化合物的混合物，三者之间的摩尔比为1：0.1～10：0.1～10。
10.按照权利要求8所述的方法，其特征在于，所述金属膦配合物的结构为
其中M为Pd、Ru或Rh，L选自PPh3；
所述金属卤化物选自铜卤化物、铁卤化物和锌卤化物中的一种或多种；
所述烃基膦化合物的结构为
其中的各个R各自独立地选自C6～C10的芳基和C1～C6的直链或支链烷基，其中至少一个R为C6～C10的芳基。
11.权利要求1～3之一所述的噻咯衍生物或者按照权利要求4～10之一方法制得的噻咯衍生物在发光部件及装置、荧光探针、生物成像、润滑油和润滑脂中的用途。
12.一种润滑脂，包括权利要求1～3之一所述的噻咯衍生物或者按照权利要求4～10之一方法制得的噻咯衍生物、稠化剂和润滑基础油。
13.按照权利要求12所述的润滑脂，其特征在于，所述噻咯衍生物占润滑脂总质量的0.01％～5.0％；所述稠化剂占润滑脂总质量的5％～30％；所述润滑基础油构成润滑脂的主要成分。
14.按照权利要求12所述的润滑脂，其特征在于，所述的稠化剂包括聚脲稠化剂、锂基稠化剂、复合锂基稠化剂、钙基稠化剂和复合铝基稠化剂中的一种或多种。
15.权利要求12～14之一所述润滑脂的制备方法，包括：将润滑基础油、稠化剂、噻咯衍生物混合炼制，研磨成脂。
16.权利要求12～14之一所述润滑脂的制备方法，其特征在于，所述润滑脂为聚脲润滑脂，其制备方法包括：将部分润滑基础油、噻咯衍生物、胺、异氰酸酯混合，在65～95℃反应10-60min，反应完全后继续升温至190～220℃进行高温炼制，然后加入剩余的基础油冷却至60～120℃，研磨成脂。
17.权利要求12～14之一所述润滑脂的制备方法，其特征在于，所述润滑脂为锂基润滑脂，其制备方法包括：将部分润滑基础油与脂肪酸在反应釜中混合加热，升温至40～90℃，加入噻咯衍生物、氢氧化锂的水溶液，加热除水后继续升温至190～220℃进行高温炼制，加入剩余的润滑基础油冷却至60～120℃，研磨成脂。
18.权利要求12～14之一所述润滑脂的制备方法，其特征在于，所述润滑脂为复合铝基润滑脂，其制备方法包括：将部分基础油、脂肪酸与小分子酸在反应釜中混合加热，升温至40～90℃，加入噻咯衍生物，将另一部分润滑基础油与醇铝化合物混合加热升温至40～100℃，待醇铝化合物全部溶解后加入到反应釜中，继续升温至190～220℃进行高温炼制，加入剩余的润滑基础油冷却至60～120℃，研磨成脂。
19.权利要求15～18之一所述润滑脂的制备方法，其特征在于，预先将噻咯衍生物溶解在溶剂中，所述溶剂为芳烃溶剂。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811212642.2A CN111072702B (zh) | 2018-10-18 | 2018-10-18 | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811212642.2A CN111072702B (zh) | 2018-10-18 | 2018-10-18 | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111072702A CN111072702A (zh) | 2020-04-28 |
| CN111072702B true CN111072702B (zh) | 2022-07-15 |
Family
ID=70308370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811212642.2A Active CN111072702B (zh) | 2018-10-18 | 2018-10-18 | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111072702B (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112876501B (zh) * | 2021-01-27 | 2022-05-31 | 淮阴工学院 | 一种基于吩噻嗪-噻咯稠杂环的有机染料及其制备方法和应用 |
| CN115074172B (zh) * | 2021-03-10 | 2023-06-09 | 中国石油化工股份有限公司 | 润滑脂及其制备方法 |
| CN115074168B (zh) * | 2021-03-11 | 2023-06-09 | 中国石油化工股份有限公司 | 润滑脂及其制备方法 |
-
2018
- 2018-10-18 CN CN201811212642.2A patent/CN111072702B/zh active Active
Non-Patent Citations (4)
| Title |
|---|
| Functionalized Siloles: Versatile Synthesis,Aggregation-Induced Emission, and Sensory and Device Applications;Zhen Li，et al.;《Adv.Funct.Mater.》;20090211;第19卷;第905-917页 * |
| Silole-Containing Polyacetylenes. Synthesis, Thermal Stability, Light Emission, Nanodimensional Aggregation, and Restricted Intramolecular Rotation;Junwu Chen，et al.;《Macromolecules》;20030122;第36卷(第4期);第1108-1117页 * |
| Synthesis, Light Emission, Nanoaggregation, and Restricted Intramolecular Rotation of 1,1-Substituted 2,3,4,5-Tetraphenylsiloles;Junwu Chen，et al.;《Chem.Mater.》;20030308;第15卷(第7期);第1535-1546页 * |
| Vapochromism and Crystallization-Enhanced Emission of 1,1-Disubstituted 2,3,4,5-Tetraphenylsiloles;Yongqiang Dong，et al.;《J.Inorg.Organomet.Polym.》;20070621;第17卷;第673-678页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111072702A (zh) | 2020-04-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111072702B (zh) | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN111072701B (zh) | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN111072706B (zh) | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN111072703B (zh) | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN111072705B (zh) | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN112552326B (zh) | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN112552332B (zh) | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN112552330B (zh) | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN111073725A (zh) | 光致发光润滑脂组合物、光致发光材料和它们的制备方法 | |
| CN112552325B (zh) | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN111072704B (zh) | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN112552329B (zh) | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN111100090B (zh) | 一种苯并氮杂环衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN112552328B (zh) | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN111100158B (zh) | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN112552327B (zh) | 一种噻咯衍生物及其制备方法、用途和光致发光润滑脂 | |
| CN111100742B (zh) | 一种复合锂基润滑脂及其制备方法 | |
| CN111073724B (zh) | 一种锂基润滑脂及其制备方法 | |
| CN111100156B (zh) | 一种噻咯衍生物及其制备方法、用途和润滑脂 | |
| CN111100157B (zh) | 一种噻咯衍生物及其制备方法、用途和润滑脂 | |
| KR101278872B1 (ko) | 디알킬 디티오카바메이트 그룹을 갖는 노보넨 디알킬 에스테르 화합물, 이를 포함하는 내마모제 및 윤활유 | |
| CN115074168B (zh) | 润滑脂及其制备方法 | |
| CN115074172B (zh) | 润滑脂及其制备方法 | |
| CN103254969A (zh) | 一种复合钙基四聚脲润滑脂及其制备方法 | |
| CN103254970A (zh) | 一种复合钙基四聚脲润滑脂及其制备方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |