CN111100158B - 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
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- CN111100158B CN111100158B CN201811268734.2A CN201811268734A CN111100158B CN 111100158 B CN111100158 B CN 111100158B CN 201811268734 A CN201811268734 A CN 201811268734A CN 111100158 B CN111100158 B CN 111100158B
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- grease
- silole
- silole derivative
- base oil
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- 239000002199 base oil Substances 0.000 claims abstract description 51
- -1 biological imaging Substances 0.000 claims abstract description 39
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- 238000006243 chemical reaction Methods 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 17
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 15
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- 238000000034 method Methods 0.000 claims description 13
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- 239000002184 metal Substances 0.000 claims description 10
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 10
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 9
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- 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
- 229910052707 ruthenium 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
- 238000000926 separation method 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
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 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
- 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
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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的结构为:
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。多苯基噻咯是一种典型的AIE化合物,近十几年来,研究人员将其应用于发光器件、荧光探针、生物成像等多个研究领域。
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的结构为:
通式(I)中,各个R各自独立地选自氢、C1-6直链或支链烷基,各个n各自独立地选自0~5之间的整数;R1、R2彼此相同或不同,各自独立地选自氢、C1-6直链或支链烷基;R3、R4、R5、R3’、R4’、R5’彼此相同或不同,各自独立地选自氢、C1-300直链或支链烷基(优选C1-10直链或支链烷基或者数均分子量Mn为300-3000的聚烯烃基)、通式(II)所示的基团,前提是R3、R4、R5中至少一个基团是通式(II)所示的基团、R3’、R4’、R5’中至少一个基团是通式(II)所示的基团;
各基团Ra彼此相同或不同,各自独立地选自氢、C1-20直链或支链烷基(优选选自C1-10直链或支链烷基)和通式(II)所示的基团;各基团Rb彼此相同或不同,各自独立地选自氢、C1-20直链或支链烷基和通式(II)所示的基团。
R3、R5优选通式(II)所示的基团;R3’、R5’优选通式(II)所示的基团;R4、R4’优选氢或通式(II)所示的基团。
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(III)所示的噻咯化合物和通式(IV)所示的炔化合物发生反应的步骤,
在通式(III)中,各个R各自独立地选自氢、C1-6直链或支链烷基,各个n各自独立地选自0~5之间的整数;各基团X彼此相同或不同,各自独立地选自F、Cl、Br、I、OH,优选Cl或Br;R1、R2彼此相同或不同,各自独立地选自氢、C1-6直链或支链烷基;R3、R4、R5彼此相同或不同,各自独立地选自氢、C1-300直链或支链烷基(优选C1-10直链或支链烷基或者数均分子量Mn为300-3000的聚烯烃基)、通式(V)所示的基团,前提是R3、R4、R5中至少一个基团是通式(V)所示的基团;
各基团Ra彼此相同或不同,各自独立地选自氢、C1-20直链或支链烷基(优选选自C1-10直链或支链烷基);各基团Rb彼此相同或不同,各自独立地选自氢、C1-20直链或支链烷基。
通式(III)所示的噻咯化合物包括:
通式(IV)所示的炔化合物包括:
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(III)所示的噻咯化合物质量的0.1%~100%(优选1%~20%)。
在所述反应中,通式(III)所示的噻咯化合物和通式(IV)所示的炔化合物之间的摩尔比优选1:1~6,最优选1:2~4。
所述反应的温度为0~50℃,优选15~35℃。
所述反应的时间为12~96h,优选24~72h。
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光,可以应用于发光部件及装置、荧光探针、成像部件、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0.0005%~5%,优选0.001%~1%;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、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、复合铝基稠化剂。
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。
根据本发明的制备方法,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)。
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。
所述润滑脂包括聚脲润滑脂或复合铝基润滑脂,其中包含的稠化剂分别为聚脲稠化剂或复合铝基稠化剂。
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。
本发明的润滑脂具有优异的光致发光性能、抗氧化性能和抗泡性能,可以用在电器工业、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上面。
具体实施方式
原料来源如下:1,1-二甲基-2,5-二溴-3,4-二苯基噻咯、3,5-二(二甲基氨基)苯乙炔、3,5-二(二乙基氨基)苯乙炔、3,5-二(二丙基氨基)苯乙炔、碘化亚铜、三苯基膦、四三苯基膦钯、十八胺、MDI、硬脂酸、苯甲酸、异丙醇铝三聚体、四氢呋喃、三乙胺、二氯甲烷、甲醇、甲苯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;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420mg(1mmol)1,1-二甲基-2,5-二溴-3,4-二苯基噻咯,733mg(3mmol)3,5-二(二乙基氨基)苯乙炔,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/甲醇(20/1,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62%。产物核磁结果为:1H NMR(400MHz,CDCl3),δ(TMS,ppm):7.11–6.85(m,10H),6.57(m,4H),6.36(m,2H),3.43(m,16H),1.27(m,24H),0.49(s,6H);MS(MALDI-TOF):m/z calcd:746.5[M]+,found:746.5。
实施例1的反应方程式如下所示:
在100mLSchlenk反应瓶中加入420mg(1mmol)1,1-二甲基-2,5-二溴-3,4-二苯基噻咯,901mg(3mmol)3,5-二(二丙基氨基)苯乙炔,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/甲醇(20/1,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507mg,产率为59%。产物核磁结果为:1H NMR(400MHz,CDCl3),δ(TMS,ppm):7.12–6.84(m,10H),6.55(m,4H),6.34(m,2H),3.42(m,16H),1.62(m,16H),0.83(m,24H),0.49(s,6H);MS(MALDI-TOF):m/z calcd:858.6[M]+,found:858.6。
实施例2的反应方程式如下所示:
在100mLSchlenk反应瓶中加入420mg(1mmol)1,1-二甲基-2,5-二溴-3,4-二苯基噻咯,565mg(3mmol)3,5-二(二甲基氨基)苯乙炔,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/甲醇(20/1,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406mg,产率为64%。产物核磁结果为:1H NMR(400MHz,CDCl3),δ(TMS,ppm):7.10–6.84(m,10H),6.55(m,4H),6.35(m,2H),3.12(m,24H),0.49(s,6H);MS(MALDI-TOF):m/z calcd:634.4[M]+,found:634.4。
实施例3的反应方程式如下所示:
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1,1-二甲基-2,5-二(3,5-二乙基氨基苯乙炔基)-3,4-二苯基噻咯溶于5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2.5克1,1-二甲基-2,5-二(3,5-二丙基氨基苯乙炔基)-3,4-二苯基噻咯溶于5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6
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1,1-二甲基-2,5-二(3,5-二甲基氨基苯乙炔基)-3,4-二苯基噻咯溶于5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。
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。
对比例2
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1,1-二甲基-2,5-二(3,5-二乙基氨基苯乙炔基)-3,4-二苯基噻咯研磨成脂。
对实施例4、实施例5、实施例6、对比例1、对比例2的润滑脂进行了性能评定,评定方法包括GB/T 3498、GB/T 269、SH/T 0325、SH/T 0719、SH/T 0324,评定结果见表1。
表1
实施例7
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10毫克1,1-二甲基-2,5-二(3,5-二乙基氨基苯乙炔基)-3,4-二苯基噻咯溶于5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10毫克1,1-二甲基-2,5-二(3,5-二丙基氨基苯乙炔基)-3,4-二苯基噻咯溶于5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10毫克1,1-二甲基-2,5-二(3,5-二甲基氨基苯乙炔基)-3,4-二苯基噻咯溶于5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7、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2。
表2分析结果
润滑脂 | 实施例7 | 实施例8 | 实施例9 | 对比例3 |
皂量/% | 10 | 10 | 10 | 10 |
滴点/℃ | 278 | 273 | 274 | 269 |
外观 | 黄色 | 黄色 | 黄色 | 黄色 |
锥入度/0.1mm | 260 | 262 | 261 | 266 |
氧化诱导期,200℃/min | 96 | 88 | 102 | 28 |
钢网分油,100℃,24h/% | 3.7 | 3.9 | 3.8 | 3.8 |
紫外灯照射下发光情况 | 黄色荧光 | 黄色荧光 | 黄色荧光 | 不发光 |
Claims (14)
5.按照权利要求3所述的方法,其特征在于,在所述反应中加入催化剂,所述催化剂选自金属膦配合物、金属卤化物和烃基膦化合物中的一种或多种。
6.按照权利要求3所述的方法,其特征在于,在所述反应中加入催化剂,所述催化剂选自金属膦配合物、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。
7.按照权利要求3所述的方法,其特征在于,在所述反应中,通式(III)所示的噻咯化合物和通式(IV)所示的炔化合物之间的摩尔比为1:1~6;所述反应的温度为0~50℃。
8.按照权利要求3所述的方法,其特征在于,在所述反应中,通式(III)所示的噻咯化合物和通式(IV)所示的炔化合物之间的摩尔比为1:2~4;所述反应的温度为15~35℃。
9.权利要求1或2的噻咯衍生物或由权利要求3~8之一方法制得的噻咯衍生物在发光部件及装置、荧光探针、成像部件、润滑油和润滑脂中的用途。
10.一种润滑脂,包括权利要求1或2的噻咯衍生物或由权利要求3~8之一方法制得的噻咯衍生物、稠化剂和润滑基础油;所述噻咯衍生物占润滑脂总质量的0.0005%~5%;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。
11.按照权利要求10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0.001%~1%;所述稠化剂占润滑脂总质量的10%~20%。
12.按照权利要求10所述的润滑脂,其特征在于,所述润滑脂包括聚脲润滑脂或复合铝基润滑脂,其中包含的稠化剂分别为聚脲稠化剂或复合铝基稠化剂。
13.权利要求10所述的润滑脂的制备方法,包括:将润滑基础油、稠化剂、噻咯衍生物混合炼制,研磨成脂。
14.权利要求12所述的润滑脂的制备方法,其特征在于,
聚脲润滑脂的制备方法包括:将部分润滑基础油、权利要求1或2的噻咯衍生物或由权利要求3~8之一方法制得的噻咯衍生物、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;
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℃,加入权利要求1或2的噻咯衍生物或由权利要求3~8之一方法制得的噻咯衍生物,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。
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