CN1504739A - 用于标记液体烃的方法 - Google Patents
用于标记液体烃的方法 Download PDFInfo
- Publication number
- CN1504739A CN1504739A CNA200310118656A CN200310118656A CN1504739A CN 1504739 A CN1504739 A CN 1504739A CN A200310118656 A CNA200310118656 A CN A200310118656A CN 200310118656 A CN200310118656 A CN 200310118656A CN 1504739 A CN1504739 A CN 1504739A
- Authority
- CN
- China
- Prior art keywords
- absorption maximum
- alkyl
- maximum scope
- anthraquinone
- anthraquinone dye
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/003—Marking, e.g. coloration by addition of pigments
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/44—Azines of the anthracene series
- C09B5/46—Para-diazines
- C09B5/48—Bis-anthraquinonediazines (indanthrone)
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
- C10L1/2235—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom hydroxy containing
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/20—Organic compounds containing halogen
- C10L1/202—Organic compounds containing halogen aromatic bond
-
- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/20—Colour, e.g. dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
一种用于标记液体石油烃的方法。该方法包括向液体石油烃添加:(i)至少一种最大吸收范围为710nm-850nm的蒽醌染料,这种蒽醌染料选自1,4,5,8-四取代的蒽醌和蒽醌二聚物;和(ii)至少一种最大吸收范围为500nm-700nm的可见染料。
Description
背景
本发明总的来说涉及一种用标示化合物的组合标记石油烃以便随后进行鉴定的方法。
US专利6,274,381公开了一种标记石油烃的方法,该方法包括用至少两种最大吸收在500nm-700nm之间的染料进行标记,由此产生多重吸收图谱,此图谱可以用来鉴定烃。然而,此文献没有提出用在其它波长范围中具有吸收性的染料标记烃的方法。
最大吸收在500nm-700nm之间的可见染料作为标示物具有很多缺陷,包括受石油烃中其它带色物质的干扰,特别是当染料以低含量存在时。本发明解决的问题是发现了用多种标示物来标记石油烃的改进方法。
发明陈述
本发明涉及一种用于标记液体石油烃的方法。该方法包括向液体石油烃添加:(i)至少一种最大吸收范围为710nm-850nm的蒽醌染料,这种蒽醌染料选自1,4,5,8-四取代的蒽醌和蒽醌二聚物;和(ii)至少一种最大吸收范围为500nm-700nm的可见染料。
详细描述
除非有另外的说明,所有的百分比均为重量百分比。以每百万分之份数计(“ppm”)的浓度是按重量/体积为基准计算的。术语“石油烃”是指以得自于石油中的烃为主要组成的产物,优选润滑油、水力流体、制动液、汽油、柴油机燃料、煤油、喷气式发动机燃料和燃料油。“烷基”是直链、支链或环状的1-20碳原子的烃基。烷基非必须地具有1个或多个双键或三键。允许烷基上取代有一个或多个卤素、羟基或烷氧基;进而可以在烷氧基上取代有一个或多个卤素取代基。优选,烷基上没有卤素或烷氧基取代基。“杂烷基”是至少一个碳被O、NR或S替换的烷基,其中R是氢、烷基、芳基或芳烷基。“芳基”是得自芳族烃化合物的取代基。芳基具有总共6-20个环原子并且具有一个或多个环,这些环是分离的或是稠合的。“芳烷基”是被“芳基”取代的“烷基”。“杂环”基团是得自于5-20个环原子的杂环化合物的取代基,其中所说的环原子中的至少一个是氮、氧或硫。优选,杂环基团不含硫原子。允许芳基或杂环基团上取代有一个或多个卤素、氰基、硝基、烷氧羰基、二烷基氨基、烷基氨基、氨基、羟基、烷基、杂烷基、烷酰基或烷氧基,同时在烷基、杂烷基、烷酰基或烷氧基上可以取代有一个或多个卤素。优选,芳基和杂环基团不含卤原子。“芳族杂环”基团是得自于芳族杂环化合物的杂环基团。
在本发明的一个优选实施方案中,向石油烃添加具有下式(I)的1,4,5,8-四取代的蒽醌染料。
式(I)中,X是R4NH、NH2、OH或卤素;并且R1、R2、R3和R4独立地是烷基、芳基、芳烷基、杂烷基或杂环基。优选,R1、R2和R3中的至少两个是芳基或芳族杂环基。更优选,X是R4NH,并且R1、R2、R3和R4中的至少三个、更优选四个全部是芳基或芳族杂环基。首选,R1、R2、R3和R4全部是芳基。
在本发明的另一个优选实施方案中,向石油烃添加呈蒽醌二聚物形式的蒽醌染料。蒽醌二聚物包括:(i)如下所示的λmax为710-850nm的6,15-二氢-5,9,14,18-二蒽并[1,2-1′,2′]哒嗪四酮取代衍生物,
也已知是商品名称为INDANTHRENE的染料;和(ii)其整个环体系中具有扩展的共轭体系、并且λmax为710-850nm的蒽醌的其它稠合二聚物。优选,蒽醌二聚物是下式(II)的取代的6,15-二氢-5,9,14,18-二蒽并[1,2-1′,2′1哒嗪四酮。
式(II)中,R1、R2、R3和R4独立地是氢、烷基、杂烷基或烷基氨基;R5是氢、烷基、杂烷基、烷基氨基、芳基氨基或芳族杂环氨基;并且R是氢、烷基、芳基氨基或芳族杂环氨基;前提条件是R和R5中的一个是芳基氨基或芳族杂环氨基。优选,R1、R2、R3和R4是氢。
在一个优选的实施方案中,R1、R2、R3、R4和R5是氢并且R是芳基氨基。优选,R是氢键供体型芳基氨基,例如苯氨基。首选,R是苯基氨基,以便化合物具有如下式(III)。
此化合物的λmax为790nm。
在另一个优选的实施方案中,R、R1、R2、R3和R4是氢并且R5是苯基氨基,以便化合物具有下式(IV)。
此化合物是6,15-二氢-8,17-二(苯基氨基)-5,9,14,18-二蒽并[1,2-1′,2′]哒嗪四酮,并且以商品名称C.I.VAT GREEN 6和CALEDON GREEN RC市售。
向石油烃中添加的最大吸收范围为710nm-850nm的各蒽醌染料的量,优选为至少0.01ppm,更优选至少0.02ppm并且首选至少0.03ppm。优选,各染料的量少于10ppm,更优选少于2ppm并且首选少于1ppm。优选,标记过程是看不见的,即通过对被标记的烃进行简单地视觉观察是检查不出染料的。本发明方法中所用的最大吸收范围为710nm-850nm的蒽醌染料,其最大吸收范围优选为720nm-850nm,更优选720nm-810nm并且首选730nm-800nm。在一个实施方案中,将至少两种在不同波长下具有最大吸收光谱、但都位于前述一个范围之内的蒽醌染料添加到石油烃中。优选,将被标记的烃置于电磁辐射下并且检测光或荧光发射的吸收,来检测蒽醌染料和可见染料,其中所说的电磁辐射的波长位于含染料最大吸收波长的光谱的一部分之中。优选,检测装置能够计算被标记的烃中的染料浓度和浓度比。当存在量为至少0.01ppm时,本领域已知的典型的分光光度计便能够检测本发明方法中所用的吸收范围为710nm-850nm的蒽醌染料。优选使用US专利5,225,679中描述的检测器,特别是Rohmand Haas公司(费城,PA)出品的SpecTraceTM分析仪。这种分析仪根据染料的吸收光谱来选择使用滤器,并且通过多元线性回归法来使用信号的化学计量分析,以便降低信噪比。
当检测方法没有涉及到对被标记的烃进行任何化学操作,则可以在测试之后将样品返回其来源,不必再对危险化学品进行处理和处置。这种情形是,例如,当通过测定被标记烃样品的光吸收来简单地检测染料时。
在本发明的一个实施方案中,将染料配制在溶剂中,以便有助于其添加到液体烃中。对四取代的蒽醌来说优选的溶剂是N-甲基吡咯烷酮、N,N-二甲基亚丙基脲、硝基苯、甲苯和N,N-二甲基甲酰胺。优选,染料以0.1%-10%的浓度存在于溶剂中。
优选,以至少0.1ppm、优选至少0.2ppm并且首选至少0.5ppm的量添加各可见染料,即最大吸收范围为500nm-700nm、优选550nm-700nm并且首选550nm-680nm的染料。优选,各可见染料的量不超过10ppm,更优选不超过5ppm,更优选不超过3ppm并且首选不超过2ppm。在一个优选的实施方案中,可见染料选自蒽醌染料和偶氮染料。最大吸收波长位于此范围内的适宜的蒽醌染料包括,例如,具有烷基氨基、芳基氨基或芳族杂环氨基取代基的1,4-二取代的蒽醌。最大吸收波长位于此范围内的适宜的偶氮染料包括双偶氮染料,例如,具有Ar-N=N-Ar-N=N-Ar结构的染料,其中Ar是芳基并且各自的Ar可以是不同的。最大吸收波长位于此范围内的适宜的商业性蒽醌和双偶氮染料的具体实例列于《色料索引(Colour Index)》中,包括C.I.Solvent Blue 98、C.I.Solvent Blue 79、C.I.Solvent Blue 99和C.I.Solvent Blue 100。
掺加至少一种最大吸收区为710nm-850nm的蒽醌染料将允许通过分光光度测定方式在相对没有干扰的光谱区鉴定液体烃。在此区域中可检测出低含量的这些染料,从而允许进行成本经济的标记过程。使用较高量的至少一种最大吸收区为500nm-700nm的可见染料有助于在此区域中的定量分光光度测定。染料含量的精确测量能够使染料的量和比例起用于鉴定烃的部分代码的作用。由于在此区域内吸收的染料通常是成本较低的,使用较高的量不会显著增加标记过程的整体成本。因此,这两种类型的染料的组合增加了灵活性并且降低了标记过程的成本。优选,被标记的液体烃的颜色没有可见的变化,即,标示物是“沉默的标示物”。
实施例
实施例1:1,4,5,8-四(苯基氨基)蒽醌的合成
将10.87g 1,4,5,8-四氯蒽醌、50g苯胺、13.4g乙酸钾、1.24g硫酸铜和3.41g苯甲醇的混合物在氮气环境下加热至130℃,并且在此温度下保持6.5小时,接着在170℃下保持另外6小时的时间。将反应混合物冷却至常温,并且过滤沉淀,得到黑色固体。将此粗产物从甲苯中重结晶,获得6.0g暗绿色晶体物料(纯度>95%,结构通过质子NMR证实为所需的产物:1,4,5,8-四(苯基氨基)蒽醌。此物料在甲苯中于750nm波长下具有最大吸收谱带(λmax)。摩尔消光系数(ε)经测定为~30,500。
实施例2:1,4,5,8-四(4-正丁基苯基氨基)蒽醌的合成
让10.87g 1,4,5,8-四氯蒽醌和95g 4-正丁基苯胺的混合物在190℃下反应12小时。然后将反应混合物冷却至70℃并且用等量乙醇稀释。放置并且进一步冷却至常温后,形成一些沉淀。将混合物过滤、洗涤并且从二甲苯/异丙醇中重结晶,获得6.6g暗绿色晶体物料(纯度>95%),其结构通过质子NMR证实为所需的产物1,4,5,8-四(4-正丁基苯基氨基)蒽醌。此物料在甲苯中于762nm波长下具有最大吸收谱带(λmax)。摩尔消光系数(ε)经测定为~36,900。实施例3:四取代的蒽醌染料在石油烃中的检测
制备1,4,5,8-四(苯基氨基)蒽醌(TPAAQ)在二甲苯、IexacoTM柴油机燃料和MobilTM普通汽油的不同浓度的溶液,并且用实验室分光光度计分析。结果示于下表中,预期的和实际的读数均按对1mg/mL读数的百分比来表达。
表
浓度,mg/mL | 预期的读数 | 实际的读数 |
在二甲苯中的TPAAQ | ||
2.045 | 204 | 208 |
1.063 | 106 | 105 |
0.983 | 98 | 98 |
0.703 | 70 | 71 |
0.402 | 40 | 40 |
0.073 | 7 | 8 |
0.035 | 4 | 3 |
在TexacoTM柴油机燃料中的TPAAQ | ||
1.35 | 135 | 135 |
1.09 | 109 | 109 |
0.84 | 84 | 85 |
0.58 | 58 | 56 |
0.33 | 33 | 33 |
0.05 | 5 | 4 |
在MobilTM普通汽油中的TPAAQ | ||
1.335 | 133 | 134 |
0.934 | 93 | 92 |
0.565 | 56 | 57 |
0.389 | 39 | 38 |
0.059 | 6 | 5 |
0.048 | 5 | 5 |
Claims (10)
1、一种用于标记液体石油烃的方法;所说的方法包括向所述液体石油烃添加:(i)至少一种最大吸收范围为710nm-850nm的蒽醌染料,这种蒽醌染料选自1,4,5,8-四取代的蒽醌和蒽醌二聚物;和(ii)至少一种最大吸收范围为500nm-700nm的可见染料。
2、权利要求1的方法,其中液体石油烃选自润滑油、水力流体、制动液、汽油、柴油机燃料、煤油、喷气式发动机燃料和燃料油。
4、权利要求3的方法,其中X是R4NH,并且R1、R2、R3和R4中的至少三个是芳基或芳族杂环基。
5、权利要求2的方法,其中所说的至少一种最大吸收范围为710nm-850nm的蒽醌染料具有(II):
其中,R1、R2、R3和R4独立地是氢、烷基、杂烷基或烷基氨基;R5是氢、烷基、杂烷基、烷基氨基、芳基氨基或芳族杂环氨基;并且R是氢、烷基、芳基氨基或芳族杂环氨基;前提条件是R和R5中的至少一个是芳基氨基或芳族杂环氨基。
6、权利要求2的方法,其中所说的至少一种最大吸收范围为500nm-700nm的可见染料选自蒽醌染料和偶氮染料。
7、权利要求6的方法,其中所说的至少一种可见染料的最大吸收范围为550nm-700nm。
8、权利要求1的方法,其中检测所说的至少一种最大吸收范围为710nm-850nm的蒽醌染料和所说的至少一种最大吸收范围为500nm-700nm的可见染料,同时不对液体石油烃进行任何化学操作。
9、权利要求8的方法,其中所说的至少一种最大吸收范围为710nm-850nm的蒽醌染料以0.02ppm-1ppm的量存在,并且所说的至少一种最大吸收范围为500nm-700nm的可见染料以0.2ppm-2ppm的量存在。
10、权利要求9的方法,其中所说的至少一种蒽醌染料的最大吸收范围为720nm-810nm。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US43061402P | 2002-12-03 | 2002-12-03 | |
US60/430,614 | 2002-12-03 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1504739A true CN1504739A (zh) | 2004-06-16 |
CN1258083C CN1258083C (zh) | 2006-05-31 |
Family
ID=32313155
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2003101186565A Expired - Fee Related CN1258083C (zh) | 2002-12-03 | 2003-11-27 | 用于标记液体烃的方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US20040106526A1 (zh) |
EP (1) | EP1426434A3 (zh) |
JP (1) | JP3806114B2 (zh) |
KR (1) | KR20040050715A (zh) |
CN (1) | CN1258083C (zh) |
BR (1) | BR0305751A (zh) |
IN (1) | IN2003MU01183A (zh) |
TW (1) | TWI247037B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104053755A (zh) * | 2011-12-06 | 2014-09-17 | 庄信万丰股份有限公司 | 示踪剂和标记烃液体的方法 |
CN112079737A (zh) * | 2020-09-29 | 2020-12-15 | 郑州原理生物科技有限公司 | 1,4,5,8-四(4-正丁基苯基氨基)蒽醌的制备方法 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3806118B2 (ja) * | 2003-06-13 | 2006-08-09 | ローム アンド ハース カンパニー | 置換アントラキノンでの炭化水素のマーキング方法。 |
US7635596B2 (en) * | 2004-12-15 | 2009-12-22 | Rohm And Haas Company | Method for monitoring degradation of lubricating oils |
US8129190B2 (en) * | 2006-11-17 | 2012-03-06 | Applied Nanotech Holdings, Inc. | Tagged petroleum products and methods of detecting same |
FR2971254B1 (fr) * | 2011-02-08 | 2014-05-30 | Total Raffinage Marketing | Compositions liquides pour marquer les carburants et combustibles hydrocarbones liquides, carburants et combustibles les contenant et procede de detection des marqueurs |
TW201435830A (zh) | 2012-12-11 | 2014-09-16 | 3M Innovative Properties Co | 不顯眼之光學標籤及其方法 |
KR101418655B1 (ko) * | 2012-12-17 | 2014-07-10 | 경북대학교 산학협력단 | 신규한 화합물 및 이를 이용한 철 이온 검출 방법 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3164449A (en) * | 1961-03-01 | 1965-01-05 | Du Pont | Anthraquinone dyes for gasoline |
US4051052A (en) * | 1970-04-28 | 1977-09-27 | Mita Industrial Company Ltd. | Liquid developer |
JPS62903A (ja) * | 1985-06-05 | 1987-01-06 | Sumitomo Chem Co Ltd | 近赤外線吸収フイルタ− |
DE3835489A1 (de) * | 1988-05-06 | 1990-04-19 | Alfred Dr Rer Nat Flath | Verwendung von additivmischungen als mittel zur erhoehung der verdampfungs- und verbrennungsgeschwindigkeit sowie der verbrennungsstabilitaet von in raketenbrennkammern oder hochleistungsbrennanlagen eingeduesten fluessigen treib- und brennstoffen |
US5880287A (en) * | 1990-05-15 | 1999-03-09 | Hyperion, Inc. | Polyoxyhydrocarbyl related products and methods for fluorescence assays |
US5525516B1 (en) * | 1994-09-30 | 1999-11-09 | Eastman Chem Co | Method for tagging petroleum products |
US6274381B1 (en) * | 1998-11-09 | 2001-08-14 | Rohm And Haas Company | Method for invisibly tagging petroleum products using visible dyes |
AU2001272257A1 (en) * | 2000-07-07 | 2002-01-21 | Medmira Inc. | Hcv mosaic antigen composition |
-
2003
- 2003-11-12 US US10/706,198 patent/US20040106526A1/en not_active Abandoned
- 2003-11-13 IN IN1183MU2003 patent/IN2003MU01183A/en unknown
- 2003-11-18 EP EP03257254A patent/EP1426434A3/en not_active Withdrawn
- 2003-11-20 TW TW092132562A patent/TWI247037B/zh not_active IP Right Cessation
- 2003-11-21 BR BR0305751-8A patent/BR0305751A/pt not_active IP Right Cessation
- 2003-11-27 CN CNB2003101186565A patent/CN1258083C/zh not_active Expired - Fee Related
- 2003-12-02 KR KR1020030086981A patent/KR20040050715A/ko not_active Application Discontinuation
- 2003-12-02 JP JP2003402771A patent/JP3806114B2/ja not_active Expired - Fee Related
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104053755A (zh) * | 2011-12-06 | 2014-09-17 | 庄信万丰股份有限公司 | 示踪剂和标记烃液体的方法 |
CN104053755B (zh) * | 2011-12-06 | 2017-02-22 | 庄信万丰股份有限公司 | 示踪剂和标记烃液体的方法 |
CN112079737A (zh) * | 2020-09-29 | 2020-12-15 | 郑州原理生物科技有限公司 | 1,4,5,8-四(4-正丁基苯基氨基)蒽醌的制备方法 |
CN112079737B (zh) * | 2020-09-29 | 2023-08-11 | 郑州原理生物科技有限公司 | 1,4,5,8-四(4-正丁基苯基氨基)蒽醌的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
JP2004197085A (ja) | 2004-07-15 |
US20040106526A1 (en) | 2004-06-03 |
TW200422396A (zh) | 2004-11-01 |
EP1426434A2 (en) | 2004-06-09 |
BR0305751A (pt) | 2004-12-21 |
EP1426434A3 (en) | 2004-11-17 |
JP3806114B2 (ja) | 2006-08-09 |
KR20040050715A (ko) | 2004-06-16 |
TWI247037B (en) | 2006-01-11 |
CN1258083C (zh) | 2006-05-31 |
IN2003MU01183A (zh) | 2006-01-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6811575B2 (en) | Method for marking hydrocarbons with anthraquinones | |
EP1479749B1 (en) | Method for marking hydrocarbons with substituted anthraquinones | |
EP1486554B1 (en) | Method for marking hydrocarbons with substituted anthraquinones | |
HU214637B (hu) | Eljárás folyadékok jelzésére IR-tartományban abszorbeáló és/vagy fluoreszkáló vegyületek alkalmazásával és a kimutatásukra szolgáló eljárás | |
CN1258083C (zh) | 用于标记液体烃的方法 | |
KR100992947B1 (ko) | 액체 탄화수소용 마커로 사용되는 피라지노포르피라진 | |
US6977177B1 (en) | Method for marking hydrocarbons with substituted anthraquinones | |
US20040102340A1 (en) | Method for marking hydrocarbons with anthraquinone imines | |
US20040110997A1 (en) | Method for marking liquid petroleum hydrocarbons |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C19 | Lapse of patent right due to non-payment of the annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |