CN1910188B - 酞菁作为液体标记物的用途 - Google Patents
酞菁作为液体标记物的用途 Download PDFInfo
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- CN1910188B CN1910188B CN2005800030468A CN200580003046A CN1910188B CN 1910188 B CN1910188 B CN 1910188B CN 2005800030468 A CN2005800030468 A CN 2005800030468A CN 200580003046 A CN200580003046 A CN 200580003046A CN 1910188 B CN1910188 B CN 1910188B
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- 239000007788 liquid Substances 0.000 title claims abstract description 18
- 239000000126 substance Substances 0.000 title claims abstract description 11
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims abstract description 67
- 239000002480 mineral oil Substances 0.000 claims abstract description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 132
- -1 two lithiums Substances 0.000 claims description 82
- 125000000623 heterocyclic group Chemical group 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
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- 125000003368 amide group Chemical group 0.000 claims description 29
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- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 14
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- 125000005842 heteroatom Chemical group 0.000 claims description 11
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
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- 125000001424 substituent group Chemical group 0.000 abstract description 7
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- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 4
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- 125000001931 aliphatic group Chemical group 0.000 description 4
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- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
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- 239000002184 metal Substances 0.000 description 1
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Substances C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
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Abstract
本发明涉及在酞菁骨架结构上带有经由亚甲基键合的取代基的特殊酞菁作为液体,尤其是矿物油的标记物的用途,涉及包含至少一种该类酞菁作为标记物的液体,尤其是矿物油。本发明还涉及在酞菁骨架结构上带有经由亚甲基键合的取代基的新型特殊酞菁。
Description
本发明涉及在基础酞菁结构上带有经由亚甲基键合的取代基的特殊酞菁作为液体,尤其是矿物油的标记物的用途,涉及包含至少一种该类酞菁作为标记物的液体,尤其是矿物油,还涉及在基础酞菁结构上带有经由亚甲基键合的取代基的新型特殊酞菁。
文献EP 0 034 725 A2尤其描述了含有咪唑基甲基的酞菁及其作为耐湿性纤维素染料的用途。
包含酞菁亚甲胺的耐絮凝且耐溶剂的酞菁颜料混合物由DE-B 1 239270所公开。
文献GB 2 328 184 A描述了具有包括杰出的流变性能在内的质量且来自具有亚甲基键合的环状基团作为取代基的颜料衍生物的添加的颜料组合物。
然而,相应取代的酞菁作为液体,尤其是矿物油的标记物的用途尚未被任何上述文献所公开。
除了其他化合物外,文献WO 94/02570 A1也建议酞菁衍生物作为液体,尤其是矿物油的标记物。
此外,文献WO 98/52950 A1建议酞菁作为液体,尤其是矿物油的标记物,其含有作为取代基的5或6元饱和含氮杂环基团,该基团经由环氮原子键合于基础酞菁结构上。
在实践中已经发现尤其是在其中通常存在添加剂的矿物油中,文献WO 94/02570 A1和WO 98/52950 A1中所公开的酞菁标记物通常不具有所需的长期稳定性。所述添加剂的作用导致标记物的特性(例如消光)在很短时间内发生变化。
因此,本发明的目的是提供其特征在于在待标记液体,尤其是矿物油中不仅具有良好的溶解度,而且具有非常良好的长期稳定性的酞菁。
因此,发现了式I的酞菁作为液体标记物的用途:
其中在式I中,
M为两个氢、两个锂、镁、锌、铜、镍、VO、TiO、AlCl、AlOCOCH3、AlOCOCF3、SiCl2或Si(OH)2,
R各自为选自-CH2-N(-X1-R1)(-X2-R2)和-CH2-Het的相同或不同结构部分,
X1、X2各自独立地为羰基或化学单键,
R1为任选被1-4个醚官能氧原子间隔的C1-C20烷基,
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基取代的C5-C7环烷基,
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基取代的5或6元饱和杂环基团,
任选被一个或多个卤素、氰基、硝基、羟基、氨基、任选被1-4个醚官能氧原子间隔的C1-C20烷基、C1-C20烷氧基、C1-C20烷基氨基或C1-C20二烷基氨基取代的C6-C10芳基,
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基、C1-C20烷氧基、C1-C20烷基氨基或C1-C20二烷基氨基取代的含3-12个碳原子的杂芳基,
任选在芳基中被一个或多个卤素、氰基、硝基、羟基、氨基、任选被1-4个醚官能氧原子间隔的C1-C20烷基、C1-C20烷氧基、C1-C20烷基氨基或C1-C20二烷基氨基取代的C6-C10芳基-C1-C4烷基,
或
在杂芳基中含3-12个碳原子的杂芳基-C1-C4烷基,所述杂芳基任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基、C1-C20烷氧基、C1-C20烷基氨基或C1-C20二烷基氨基取代,
R2为氢或独立于R1地如对R1所定义,且当X2为羰基时,R2不为氢,
Het为任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基取代且其中一个CH2基团任选被羰基替代的5、6或7元饱和杂环基团,
或
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基取代的含3-12个碳原子的杂芳基,
该饱和杂环基团或杂芳基经由合适的杂原子或碳原子键合于-CH2-Het结构部分的CH2基团上,
和
n在每种情况下独立地为0、1、2、3或4的值,条件是4个n值的总和至少为1。
任选被1-4个醚官能氧原子间隔的C1-C20烷基例如包括甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、新戊基、叔戊基、己基、2-甲基戊基、庚基、庚-3-基、辛基、2-乙基己基、异辛基、壬基、异壬基、癸基、异癸基、十一烷基、十二烷基、十三烷基、3,5,5,7-四甲基壬基、异十三烷基(上述术语异辛基、异壬基、异癸基和异十三烷基是俗名且源于通过羰基合成法得到的醇-关于该主题,参见UllmannsEncyklopdie der technischen Chemie,第4版,第7卷,第215-217页和第11卷,第435-436页)、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基、二十烷基、甲氧基甲基、2-乙基己氧基甲基、2-甲氧基乙基、2-乙氧基乙基、2-丙氧基乙基、2-异丙氧基乙基、2-丁氧基乙基、2-或3-甲氧基丙基、2-或3-乙氧基丙基、2-或3-丙氧基丙基、2-或3-丁氧基丙基、2-或4-甲氧基丁基、2-或4-乙氧基丁基、2-或4-丙氧基丁基、2-或4-丁氧基丁基、3,6-二氧杂庚基、3,6-二氧杂辛基、4,8-二氧杂壬基、3,7-二氧杂辛基、3,7-二氧杂壬基、4,7-二氧杂辛基、4,7-二氧杂壬基、4,8-二氧杂癸基、3,6,8-三氧杂癸基、3,6,9-三氧杂十一烷基、3,6,9,12-四氧杂十三烷基或3,6,9,12-四氧杂十四烷基。
有用的C5-C7环烷基包括环戊基、环己基和环庚基。这些环烷基也任选被一个或多个,尤其是至多三个也任选被1-4个醚官能氧原子间隔的C1-C20烷基取代。也任选被氧原子间隔的该类C1-C20烷基的实例已经在上面列举。
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基取代的5或6元饱和杂环基团例如衍生于吡咯烷,2-或3-甲基吡咯烷,2,4-二甲基-3-乙基吡咯烷,吡唑烷,2-、3-、4-或5-甲基吡唑烷,咪唑烷,2-、3-、4-或5-甲基咪唑烷,唑烷,2-、4-或5-甲基唑烷,异唑烷,3-、4-或5-甲基异唑烷,哌啶,2-、3-、4-甲基-或2-、3-、4-乙基哌啶,2,6-二甲基哌啶,哌嗪,4-(C1-C4烷基)哌嗪,如4-甲基-或4-乙基哌嗪,吗啉,硫代吗啉或硫代吗啉S,S-二氧化物。术语“衍生”在上下文中应解释为所衍生的基团例如通过夺取碳原子或若存在的话,杂原子所键合的氢原子而由上述杂环得到的效果。例如,哌啶-1-基和哌啶-2-基通过夺取氮键合的氢原子或夺取在2位的碳键合的氢原子而衍生于哌啶。
当R1和R2对应于任选取代的5或6元饱和杂环基团且X1和X2均被定义为化学单键时,该基团经由5或6元杂环基团的碳原子键合于-CH2-N(-X1-R1)(-X2-R2)结构部分的氮原子上。
C6-C10芳基尤其包括苯基和萘基。这些基团任选被一个或多个卤素如氟、氯或溴,氰基,硝基,羟基,氨基,任选被1-4个醚官能氧原子间隔的C1-C20烷基,C1-C20烷氧基,C1-C20烷基氨基或C1-C20二烷基氨基取代。任选被1-4个醚官能氧原子间隔的对应C1-C20烷基或存在于C1-C20烷氧基、C1-C20烷基氨基或C1-C20二烷基氨基中的C1-C20烷基作为举例已经在上面列举。
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基、C1-C20烷氧基、C1-C20烷基氨基或C1-C20二烷基氨基取代的含3-12个碳原子的杂芳基例如衍生于吡咯,呋喃,噻吩,吡唑,异唑,异噻唑,咪唑,1H-1,2,3-三唑,1H-1,2,4-三唑,吡啶,吡嗪,哒嗪,1H-吖庚因,2H-吖庚因,唑,噻唑,1,2,3-、1,2,4-或1,3,4-二唑,1,2,3-、1,2,4-或1,3,4-噻二唑以及若合适的话还有苯并-或二苯并稠合环,例如喹啉、异喹啉、吲哚、苯并[b]呋喃(苯并呋喃)、苯并[b]噻吩(硫茚)、咔唑、二苯并呋喃、二苯并噻吩、1H-吲唑、indoxazole、苯并[d]异噻唑、anthranil、苯并咪唑、苯并唑、苯并噻唑、噌啉、2,3-二氮杂萘、喹唑啉、喹喔啉或吩嗪。任选被1-4个醚官能氧原子间隔的C1-C20烷基取代基作为举例已经在上面列举。
当R1和R2对应于任选取代的杂芳基且X1和X2均被定义为化学单键时,该基团经由杂芳基的碳原子键合于-CH2-N(-X1-R1)(-X2-R2)结构部分的氮原子上。
在芳基中任选被一个或多个卤素、氰基、硝基、羟基、氨基、任选被1-4个醚官能氧原子间隔的C1-C20烷基、C1-C20烷氧基、C1-C20烷基氨基或C1-C20二烷基氨基取代的C6-C10芳基-C1-C4烷基尤其包括苄基、苯基乙基、3-苯基丙基和4-苯基丁基。合适的任选被1-4个醚官能氧原子间隔的C1-C20烷基或C1-C20烷氧基、C1-C20烷基氨基或C1-C20二烷基氨基中存在的C1-C20烷基作为举例已经在上面列举。
在杂芳基中含3-12个碳原子且杂芳基任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基、C1-C20烷氧基、C1-C20烷基氨基或C1-C20二烷基氨基取代的杂芳基-C1-C4烷基例如衍生于已在上面提到的杂芳基,该杂芳基经由杂芳基的碳原子或适于键合的杂原子键合于C1-C4烷基。合适的任选被1-4个醚官能氧原子间隔的C1-C20烷基或C1-C20烷氧基、C1-C20烷基氨基或C1-C20二烷基氨基中存在的C1-C20烷基作为举例已经在上面列举。
除了已经作为举例提到的衍生于对应的5或6元杂环的任选取代的5或6元饱和杂环基团外,对Het变量而言可能的基团通常额外包括衍生于对应七元杂环的那些七元基团。七元杂环的实例包括氧杂庚环、硫杂庚环和氮杂庚环。此外,还可能的是其中一个CH2基团已经被羰基替代的5、6或7元基团。所述基团尤其是5、6或7元内酯或内酰胺基团。
通常而言,饱和杂环基团或杂芳基经由合适的杂原子或碳原子键合于-CH2-Het结构部分的CH2基团上。
在上述内酰胺情况下,与-CH2-Het结构部分的CH2基团的键合优选经由环氮原子而进行。
优选使用如下式I的酞菁,其中M为两个氢、两个锂、镁、锌、铜、镍、VO、TiO、AlCl、AlOCOCH3、AlOCOCF3、SiCl2或Si(OH)2,R各自为相同或不同的-CH2-Het结构部分,Het为任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代且其中一个CH2基团任选被羰基替代的5、6或7元饱和杂环基团,或任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代的含3-5个碳原子的杂芳基。
特别优选使用如下式I的酞菁,其中M为两个氢、两个锂、镁、锌、铜、镍、VO、TiO、AlCl、AlOCOCH3、AlOCOCF3、SiCl2或Si(OH)2,R各自为相同或不同的-CH2-Het结构部分且Het为任选被一个或多个C1-C4烷基取代且其中一个CH2基团任选被羰基替代的5、6或7元饱和杂环基团,或任选被一个或多个C1-C4烷基取代的含3-5个碳原子的杂芳基。
特别有利的是使用如下式I的酞菁,其中M为两个氢,R为相同或不同的-CH2-Het结构部分,Het为任选被一个或多个C1-C4烷基取代且其中与氮原子相邻的CH2基团被羰基替代的5、6或7元饱和含氮基团或任选被一个或多个C1-C4烷基取代的含3-5个碳原子的含氮杂芳基。
在所有上述优选情形中,式I酞菁中的饱和杂环基团或杂芳基经由合适的氮原子或碳原子键合于-CH2-Het结构部分的CH2基团上;此外,式I中的变量n优选在每种情况下独立地取0、1或2的值,条件是4个n值的总和至少为1。
在前述优选情形下对Het所规定的基团也作为举例已经在上面列举。
特别令人感兴趣的是使用如下式I的酞菁,其中M为两个氢,R为相同的-CH2-Het结构部分,Het为任选被一个或多个C1-C4烷基取代且经由氮原子键合于-CH2-Het结构部分的CH2基团上的γ-丁内酰胺、δ-戊内酰胺或ε-己内酰胺基团,以及n在每种情况下独立地为0、1或2的值,条件是4个n值的总和至少为1。
进一步优选使用如下式I的酞菁,其中M为两个氢、两个锂、镁、锌、铜、镍、VO,TiO,AlCl、AlOCOCH3、AlOCOCF3、SiCl2或Si(OH)2,R各自为选自-CH2-N(-X1-R1)(-X2-R2)的相同或不同结构部分,X1、X2各自独立地为羰基或化学单键,R1为任选被1-4个醚官能氧原子间隔的C1-C15烷基,任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代的环己基,任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代的5或6元饱和杂环基团,任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基、C1-C15烷氧基、C1-C15烷基氨基或C1-C15二烷基氨基取代的C6-C10芳基,任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基、C1-C15烷氧基、C1-C15烷基氨基或C1-C15二烷基氨基取代的含3-5个碳原子的杂芳基,在芳基中任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基、C1-C15烷氧基、C1-C15烷基氨基或C1-C15二烷基氨基取代的苯基-C1-C4烷基,或在杂芳基中含3-5个碳原子且杂芳基任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基、C1-C15烷氧基、C1-C15烷基氨基或C1-C15二烷基氨基取代的杂芳基-C1-C4烷基,以及R2为氢或独立于R1地如对R1所定义,且当X2为羰基时,R2不为氢。
特别优选使用如下式I的酞菁,其中M为两个氢,R各自为选自-CH2-N(-X1-R1)(-X2-R2)的相同或不同结构部分,X1、X2各自独立地为羰基或化学单键,R1为任选被1-4个醚官能氧原子间隔的C1-C15烷基,任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代的环己基,任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代的5或6元饱和杂环基团,任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基、C1-C15烷氧基、C1-C15烷基氨基或C1-C15二烷基氨基取代的苯基,在芳基中任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基、C1-C15烷氧基、C1-C15烷基氨基或C1-C15二烷基氨基取代的苯基-C1-C4烷基,以及R2为氢或独立于R1地如对R1所定义,且当X2为羰基时,R2不为氢。
在上述优选情形中,变量n优选在每种情况下独立地取0、1或2的值,条件是4个n值的总和至少为1。
在前述优选情形下对R1和R2所规定的基团也作为举例已经在上面列举。
按照本发明可以借助上面详细描述的式I的酞菁及其优选实施方案标记的合适液体是尤其是有机液体,例如醇类如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、仲丁醇、戊醇、异戊醇、新戊醇或己醇;二醇类如1,2-乙二醇,1,2-或1,3-丙二醇,1,2-、2,3-或1,4-丁二醇,二甘醇,三甘醇,二丙二醇或三丙二醇;醚类如甲基叔丁基醚、1,2-乙二醇单甲醚、1,2-乙二醇二甲醚、1,2-乙二醇单乙醚、1,2-乙二醇二乙醚、3-甲氧基丙醇、3-异丙氧基丙醇、四氢呋喃或二烷;酮类如丙酮、甲基乙基酮或双丙酮醇;酯类如乙酸甲酯、乙酸乙酯、乙酸丙酯或乙酸丁酯;脂族或芳族烃类如戊烷、己烷、庚烷、辛烷、异辛烷、石油醚、甲苯、二甲苯、乙苯、1,2,3,4-四氢化萘、十氢化萘、二甲基萘、石油溶剂;矿物油如汽油、煤油、柴油或加热油;天然油如橄榄油、豆油或葵花油;或天然或合成机油、液压油或传动油,如汽车机油或缝纫机油;或制动液。
特别有利的是将上述式I的酞菁及其优选实施方案用于标记矿物油。
本发明进一步提供了包含至少一种式I的酞菁或其优选实施方案作为标记物的液体。
尤其要求保护包含至少一种式I的酞菁或其优选实施方案作为标记物的矿物油。
式I的酞菁还可以用作添加剂浓缩物(在下文中按照相关命名法也称为包装物)的组分,所述浓缩物除了载体油和不同燃料添加剂的混合物之外通常还包含染料以及为了隐形价格(invisible fiscal)或制造商区别标识而包含另外的标记物。这些包装物使得可从未添加的矿物油槽供应给不同的矿物油经销商,其中对于公司区别添加,例如仅在将矿物油装入合适的运输容器时,借助它们各自的包装物而赋予颜色和标记物。
该类包装物中所含的组分尤其是:
a)至少一种式I的酞菁或其优选实施方案,
b)至少一种载体油,
c)至少一种选自清洁剂、分散剂和阀座磨损抑制添加剂的添加剂,
d)以及如果合适的话其它添加剂和助剂。
所用载体油通常为粘稠、高沸点且尤其是热稳定的液体。它们用薄液膜覆盖热金属表面如进气阀,因此防止或延缓分解产物在金属表面的形成和沉积。
可用作燃料和润滑剂添加剂浓缩物组分b)的载体油例如为矿物载体油(基础油),尤其是溶剂中性(SN)500-2000粘度级别的那些,基于MN=400-1800的烯烃聚合物,尤其是基于聚丁烯或聚异丁烯(氢化或未氢化)、基于聚-α-烯烃或聚内烯烃的合成载体油以及基于烷氧基化长链醇或酚的合成载体油。根据本发明,用作载体油的氧化乙烯、氧化丙烯和/或氧化丁烯与聚丁基醇或聚异丁烯醇的加合物例如描述于EP 277 345 A1中;根据本发明使用的其它聚烯烃醇聚烷氧基化物描述于WO 00/50543 A1中。待使用的其它载体油还包括如在WO 00/61708中详细描述的聚烯烃醇聚醚胺。
应当理解也可以使用不同载体油的混合物,只要它们互相相容并且与包装物的其它组分相容即可。
例如由来自空气的粉尘颗粒和来自燃烧室的未燃烧烃产生的杂质不但使内燃机的汽化器和进气系统的污染程度增加,还使用于计量供入燃料的喷射系统的污染程度增加。
为减少或防止这些污染,在燃料中加入添加剂(“清洁剂”)以使阀和汽化器或喷射系统保持清洁。这类清洁剂通常与一种或多种载体油组合使用。载体油发挥了额外的“洗涤功能”,支持并经常促进清洁剂在清洁和保持清洁方面的作用,因此它们可有助于减少清洁剂的所需量。
在此还应提及的是,许多通常用作载体油的物质表现出作为清洁剂和/或分散剂的额外作用,这就是为什么在这种情况下清洁剂和/或分散剂的比例可以减少的原因。这类具有清洁剂/分散剂作用的载体油例如详细描述于刚提及的WO文献中。
经常也不可能清楚地区分清洁剂、分散剂和阀座磨损抑制添加剂的作用模式,这就是为什么将这些化合物汇集于组分c)下的原因。可在包装物中应用的常规清洁剂例如列于WO 00/50543 A1和WO 00/61708 A1中并且包括:
可根据EP-A 244 616通过使高反应性聚异丁烯加氢甲酰基化,并随后用氨、一元胺或多胺如二亚甲基氨基丙胺、乙二胺、二亚乙基三胺、三亚乙基四胺或四亚乙基五胺还原胺化而得到的聚异丁烯胺,可通过使主要在β位和γ位具有双键的聚丁烯或聚异丁烯氯化,并随后用氨、一元胺或上述多胺胺化而得到的聚(异)丁烯胺,可通过用空气或臭氧使聚(异)丁烯中的双键氧化而得到羰基化合物或羧基化合物,并随后在还原(氢化)条件下胺化而得到的聚(异)丁烯胺,
可根据DE-A 196 20 262通过使聚异丁烯环氧化物与胺反应,并随后使氨基醇脱水并还原而得到的聚异丁烯胺,
可根据WO-A 97/03946通过使平均聚合度P为5-100的聚异丁烯与氮氧化物或者氮氧化物与氧气的混合物反应,并随后使这些反应产物氢化而得到的任选含有羟基的聚异丁烯胺,
可根据EP-A 476 485通过使聚异丁烯环氧化物与氨、一元胺或上述多胺反应而得到的含羟基的聚异丁烯胺,
可通过使C2-C30链烷醇、C6-C30链烷二醇、单C2-C30烷基胺、二C2-C30烷基胺、C1-C30烷基环己醇或C1-C30烷基酚与基于单位羟基或氨基为1-30mol的氧化乙烯和/或氧化丙烯和/或氧化丁烯反应,并随后用氨、一元胺或上述多胺还原胺化而得到的聚醚胺,以及
可根据EP-A 831 141通过使聚异丁烯取代的酚与醛和一元胺或上述多胺反应而得到的“聚异丁烯曼尼希碱”。
待使用的其它清洁剂和/或阀座磨损抑制添加剂例如列于WO 00/47698 A1中以及包括具有至少一个数均分子量(MN)为85-20000的疏水烃基且具有至少一个选自如下的极性结构部分的化合物:
(i)单氨基或其中至少一个氮原子具有碱性的含至多6个氮原子的多氨基;
(ii)任选与羟基组合的硝基;
(iii)与单氨基或其中至少一个氮原子具有碱性的多氨基组合的羟基;
(iv)羧基或者它们的碱金属盐或碱土金属盐;
(v)磺酸基或者它们的碱金属盐或碱土金属盐;
(vi)由羟基、单氨基或其中至少一个氮原子具有碱性的多氨基,或者由氨基甲酸酯基封端的聚氧化C2-C4烯基;
(vii)羧酸酯基;
(viii)衍生于琥珀酸酐且具有羟基和/或氨基和/或酰胺基和/或亚氨基的结构部分;和/或
(ix)通过酚羟基与醛和一元胺或多胺的曼尼希反应而得到的结构部分。
含有单氨基或多氨基(i)的添加剂优选为基于聚丙烯或者基于MN=300-5000的高反应性(即主要具有末端双键,通常在β-和γ-位)或常规的(即主要具有内双键)聚丁烯或聚异丁烯的聚烯烃一元胺或聚烯烃多胺。可通过使聚异丁烯(其可含有至多20重量%正丁烯单元)加氢甲酰基化,并且用氨,一元胺或者多胺如二甲氨基丙胺、乙二胺、二亚乙基三胺、三亚乙基四胺或四亚乙基五胺还原胺化而制备的基于高反应性聚异丁烯的这类添加剂尤其公开于EP 244 616 A2中。当将主要具有内双键(通常在β-和γ-位)的聚丁烯或聚异丁烯作为原料用于制备添加剂时,可能的制备路线为氯化并随后胺化,或者用空气或臭氧使双键氧化而得到羰基或羧基化合物,并随后在还原(氢化)条件下胺化。此处用于胺化的胺可以与上面用于使加氢甲酰基化的高反应性聚异丁烯还原胺化的那些相同。基于聚丙烯的相应添加剂尤其描述于WO 94/24231 A1中。
含有单氨基(i)的其它优选添加剂为平均聚合度P=5-100的聚异丁烯与氮氧化物或者氮氧化物和氧气的混合物的反应产物的氢化产物,尤其如WO 97/03946 A1所述。
含有单氨基(i)的其它优选添加剂为可通过使聚异丁烯环氧化物与胺反应,并随后使氨基醇脱水和还原而得到的化合物,尤其如DE 196 20 262 A1所述。
含有任选与羟基组合的硝基(ii)的添加剂优选为平均聚合度P为5-100或10-100的聚异丁烯与氮氧化物或者氮氧化物和氧气的混合物的反应产物,尤其如WO 96/03367 A1和WO 96/03479 A1所述。这些反应产物通常为纯硝基聚异丁烷(如α,β-二硝基聚异丁烷)和混合羟基硝基聚异丁烷(如α-硝基-β-羟基聚异丁烷)的混合物。
含有与单氨基或多氨基组合的羟基(iii)的添加剂尤其是可由优选主要具有末端双键且MN=300-5000的聚异丁烯得到的聚异丁烯环氧化物与氨、一元胺或多胺的反应产物,尤其如EP 476 485 A1所述。
含有羧基或者它们的碱金属盐或碱土金属盐(iv)的添加剂优选为C2-C40烯烃与马来酸酐的如下共聚物,所述共聚物的总摩尔质量为500-20000并且其部分或全部羧基已转化为碱金属盐或碱土金属盐并且任何剩余的羧基已与醇或胺反应。这类添加剂尤其公开于EP 307 815 A1中。这类添加剂主要用来防止阀座磨损且可以如WO 87/01126 A1中所述有利地与常规清洁剂如聚(异)丁烯胺或聚醚胺组合使用。
含有磺酸基或者它们的碱金属盐或碱土金属盐(v)的添加剂优选为烷基磺基琥珀酸的碱金属盐或碱土金属盐,尤其如EP 639 632 A1所述。这类添加剂主要用来防止阀座磨损且可有利地与常规清洁剂如聚(异)丁烯胺或聚醚胺组合使用。
含有聚氧化C2-C4亚烷基结构部分(vi)的添加剂优选为聚醚或聚醚胺,其可通过使C2-C60链烷醇、C6-C30链烷二醇、单C2-C30烷基胺、二C2-C30烷基胺、C1-C30烷基环己醇或C1-C30烷基酚与基于单位羟基或氨基为1-30mol氧化乙烯和/或氧化丙烯和/或氧化丁烯反应,以及在聚醚胺的情况下,随后用氨、一元胺或多胺还原胺化而得到。这类产物尤其描述于EP 310 875 A1、EP 356 725 A1、EP 700 985 A1和US4,877,416中。在聚醚的情况下,这类产物还具有载体油的性能。这些化合物的典型实例为十三烷醇丁氧基化物、异十三烷醇丁氧基化物、异壬基酚丁氧基化物、聚异丁烯醇丁氧基化物和聚异丁烯醇丙氧基化物以及与氨的相应反应产物。
含有羧酸酯基团(vii)的添加剂优选为一元羧酸、二羧酸或三羧酸与长链链烷醇或多元醇,尤其是在100℃下最小粘度为2mm2/s的那些醇的酯,尤其如DE 38 38 918 A1所述。使用的一元羧酸、二羧酸或三羧酸可为脂族酸或芳族酸,特别适合的酯醇或酯多元醇例如为具有6-24个碳原子的长链代表。酯的典型代表为异辛醇、异壬醇、异癸醇和异十三烷醇的己二酸酯、邻苯二甲酸酯、间苯二甲酸酯、对苯二甲酸酯和偏苯三酸酯。这类产物也具有载体油的性能。
含有衍生于琥珀酸酐且具有羟基和/或氨基和/或酰胺基和/或亚氨基的结构部分(viii)的添加剂优选为可通过使MN=300-5000的常规或高反应性聚异丁烯与马来酸酐由热路线或经由氯化的聚异丁烯反应而得到的对应的聚异丁烯基琥珀酸酐衍生物。特别有用的是脂族多胺如乙二胺、二亚乙基三胺、三亚乙基四胺或四亚乙基五胺的衍生物。这类汽油燃料添加剂尤其描述于US4,849,572中。
含有通过酚羟基与醛和一元胺或多胺的曼尼希反应得到的结构部分(ix)的添加剂优选为聚异丁烯取代的酚与甲醛和一元胺或多胺如乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺或二甲氨基丙胺的反应产物。聚异丁烯取代的酚可源于MN=300-5000的常规或高反应性聚异丁烯。这类“聚异丁烯-曼尼希碱”尤其描述于EP 831 141 A1中。
对于各自详述的添加剂的更精确定义,在此明确参考上述现有技术文献的公开。
作为组分c)的分散剂例如为聚异丁烯琥珀酸酐的酰亚胺、酰胺、酯、铵盐和碱金属盐。这些化合物尤其用于润滑油中,但有时也作为清洁剂用于燃料组合物中。
如果需要的话可作为包装物的组分d)存在的其它添加剂和助剂为:
有机溶剂,例如醇类如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、仲丁醇、戊醇、异戊醇、新戊醇或己醇,例如二醇如1,2-乙二醇、1,2-或1,3-丙二醇、1,2-、2,3-或1,4-丁二醇、二甘醇、三甘醇、二丙二醇或三丙二醇,例如醚类如甲基叔丁基醚、1,2-乙二醇单甲醚、1,2-乙二醇二甲醚、1,2-乙二醇单乙醚、1,2-乙二醇二乙醚、3-甲氧基丙醇、3-异丙氧基丙醇、四氢呋喃或二烷,例如酮类如丙酮、甲基乙基酮或双丙酮醇,例如酯类如乙酸甲酯、乙酸乙酯、乙酸丙酯或乙酸丁酯,例如内酰胺如N-甲基吡咯烷酮(NMP),例如脂族或芳族烃类及其混合物如戊烷、己烷、庚烷、辛烷、异辛烷、石油醚、甲苯、二甲苯、乙苯、1,2,3,4-四氢化萘,十氢化萘、二甲基萘或石油溶剂,以及例如矿物油如汽油,煤油,柴油或加热油,
缓蚀剂,例如在铁类金属防腐的情况下,基于具有成膜倾向的有机羧酸的铵盐或杂环芳族化合物的铵盐,
抗氧化剂或稳定剂,例如基于胺如对苯二胺、二环己基胺或其衍生物,或者基于酚如2,4-二叔丁基酚或3,5-二叔丁基-4-羟苯基丙酸,
破乳剂,
抗静电剂,
茂金属如二茂铁或甲基环戊二烯基三羰基锰,
润滑性能改进剂(润滑添加剂)如某些脂肪酸、链烯基琥珀酸酯、二(羟烷基)脂肪胺、羟基乙酰胺或蓖麻油,
降低燃料pH的胺,
除式I的酞菁及其优选实施方案以外的其它标记物,以及
染料。
通常选择组分a),即至少一种式I的酞菁或其优选实施方案在包装物中的浓度量级,以使将包装物加入矿物油之后在其中存在所需浓度的标记物。标记物在矿物油中的典型浓度例如为0.01重量ppm至数十重量ppm。
组分b),即至少一种载体油在包装物中的存在浓度通常为1-50重量%,尤其是5-30重量%,且组分c),即至少一种清洁剂和/或至少一种分散剂在包装物中的存在浓度通常为25-90重量%,尤其是30-80重量%,在每种情况下基于组分a)-c)和若存在的话,d)的总量,其中组分a)-c)和若存在的话,d)各自的浓度之和为100重量%。
当缓蚀剂、抗氧化剂或稳定剂、破乳剂、抗静电剂、茂金属、润滑性能改进剂和用于降低染料pH的胺作为组分d)存在于包装物中时,它们的浓度之和基于包装物的总重量(即组分a)-c)以及d)的总量)通常不超过10重量%,缓蚀剂和破乳剂的浓度范围在每种情况下通常为包装物总量的约0.01-0.5重量%。
当另外的(即还没有随剩余组分引入的)有机溶剂作为组分d)存在于包装物中时,它们的浓度之和基于包装物的总量通常不超过20重量%。这些溶剂通常源于标记物和/或染料溶液,为了更精确地计量,通常在包装物中加入溶液而不是纯标记物和/或染料。
当式I的酞菁或其优选实施方案以外的其它标记物作为组分d)存在于包装物中时,它们的浓度又基于在将包装物加入矿物油后它们将具有的含量。这已经在组分a)中说明,使用时加以必要的变更。
当染料作为组分d)存在于包装物中时,它们的浓度基于包装物的总量通常例如为0.1-5重量%。
在本发明上下文中额外要求保护的是式Ia的酞菁:
其中M为两个氢、两个锂、镁、锌、铜、镍、VO、TiO、AlCl、AlOCOCH3、AlOCOCF3、SiCl2或Si(OH)2,R各自为相同或不同的-CH2-Het结构部分,Het为任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基取代且其中一个CH2基团任选被羰基替代的5、6或7元饱和杂环基团,该饱和杂环基团经由合适的杂原子或碳原子键合于-CH2-Het结构部分的CH2基团上。变量n在每种情况下独立地取0、1、2、3或4的值,条件是4个n值的总和至少为1。
在优选的式I的酞菁中,M为两个氢、两个锂、镁、锌、铜、镍、VO、TiO、AlCl、AlOCOCH3、AlOCOCF3、SiCl2或Si(OH)2,R各自为相同或不同的-CH2-Het结构部分,Het为任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代且其中一个CH2基团任选被羰基替代的5、6或7元饱和杂环基团。
特别优选的酞菁是如下那些,其中在式Ia中,M为两个氢、两个锂、镁、锌、铜、镍、VO、TiO、AlCl、AlOCOCH3、AlOCOCF3、SiCl2或Si(OH)2,R为相同或不同的-CH2-Het结构部分,Het为任选被一个或多个C1-C4烷基取代且其中一个CH2基团任选被羰基替代的5、6或7元饱和杂环基团。
特别令人感兴趣的是如下酞菁,其中在式Ia中,M为两个氢,R为相同或不同的-CH2-Het结构部分,Het为任选被一个或多个C1-C4烷基取代且其中与氮原子相邻的CH2基团任选被羰基替代的5、6或7元饱和杂环基团。
在上述优选情形中,式Ia的酞菁中的饱和杂环基团经由合适的氮原子或碳原子键合于-CH2-Het结构部分的CH2基团上;此外,在式Ia中,变量n优选在每种情况下独立地取0、1或2的值,条件是4个n值的总和至少为1。
非常特别令人感兴趣的是如下酞菁,其中在式Ia中,M为两个氢,R为相同的-CH2-Het结构部分,Het为任选被一个或多个C1-C4烷基取代且经由氮原子键合于-CH2-Het结构部分的CH2基团上的γ-丁内酰胺、δ-戊内酰胺或ε-己内酰胺基团,以及n在每种情况下独立地为0、1或2的值,条件是4个n值的总和至少为1。
这里应清楚的是变量n的值各自涉及上述式I和Ia化合物的单个分子且因此必定为整数。然而,当考虑全部分子时,正如因合成通常所得到的那样,从统计学上讲对键合于基础酞菁结构的各苯环的R基团的平均数而言当然可以是有理数值。
式I和Ia的酞菁可以通过与对应的羟甲基化化合物在浓酸中反应而由未取代的酞菁得到(方法A),此时羟甲基化化合物可以通过本领域熟练技术人员通常已知的方法得到。由内酰胺制备羟甲基内酰胺例如描述于文献US4,769,454和US3,073,843中。
此外,式I和Ia的酞菁还可以与氮化合物如酰胺、内酰胺、咪唑等和低聚甲醛在酸存在下反应而得到所需标记物(方法B)。
反应条件(温度、反应时间、浓度、羟甲基化合物的过量等)可以控制酞菁的取代度并因此控制其溶解度。取代度例如可以通过质谱法测定。
酞菁1:
该化合物通过方法A和B二者制备:
方法A:
起始在40-45℃下加入100g聚磷酸,在20分钟内引入5.14g(0.010mol)不含金属的酞菁,将该混合物进一步搅拌30分钟并在20分钟内加入8.0g(0.040mol)4-叔丁基-N-羟甲基己内酰胺。将该混合物在105℃下再搅拌8小时,然后冷却至50℃,随后用500g冰水稀释并吸滤。将潮湿残余物溶于600ml水中并使用浓氢氧化钠溶液调节至pH为12.5。进一步搅拌该混合物2小时,过滤并减压干燥。产量为7g。上式中的mA平均值为3-4。
方法B:
初始在40-45℃下加入100g聚磷酸并在20分钟内引入5.14g(0.010mol)不含金属的酞菁和2.2g(0.075mol)低聚甲醛。然后将混合物在50℃下再搅拌4小时并加入12.7g(0.075mol)4-叔丁基己内酰胺。将该混合物在105℃下进一步搅拌7.5小时,然后冷却至50℃,随后用500g冰水稀释并吸滤。将潮湿残余物溶于600ml水中并使用浓氢氧化钠溶液调节至pH为12.5。进一步搅拌该混合物2小时,过滤并减压干燥。产量为10g。上式中的mB平均值约为4。
以类似方式制备如下所示的酞菁2-5:
酞菁2(由方法A(mA为3-4)和B(mB约为4)制备):
酞菁3(由方法B制备(mB约为4)):
酞菁4(由方法B制备(mB约为4)):
酞菁5(由方法B制备(mB约为4)):
酞菁6(对比;根据WO 98/52950 A1的实施例1制备):
长期稳定性:
在市售矿物油燃料清洁剂(聚异丁烯胺(PIBA);PIBA含量为50重量%的溶液)存在下研究酞菁1和2以及酞菁6(对比)的长期稳定性。为此,将50-100mg特定化合物溶于50ml Shellsol AB中,或当该化合物在ShellsolAB中的溶解度不足时,首先用约5ml异丙醇或N-甲基吡咯烷酮初溶,然后使用Shellsol AB配成50ml。随后将该溶液滤过槽纹滤纸。
将1-3mol滤液用清洁剂配成10ml(对应于该特定化合物的浓度为0.01-0.08%)并在1mm比色杯中相对于未添加的对应参比进行分析。
将样品转移至10ml安瓿中,以气密的方式密封并在50℃的水浴中储存。
试验再现于下表中。将所有测量值标准化为起始消光。
在50℃下的长期稳定性相比于清洁剂的比较
酞菁 | 储存时间(小时) | 最大吸收(nm) | 消光(标准化) |
6(对比) | 0114161283 | 768 | 1.000.330.200.05 |
1 | 016163474524 | 599 | 1.000.980.970.950.93 |
2 | 0114161283474668 | 695 | 1.000.890.880.780.770.81 |
然而,在酞菁6(对比)的情况下,标准化消光在283小时后下降为初始值的5%,酞菁1和2的值分别在明显更长的储存时间524和668小时后仍分别为初始值的93%和81%。
Claims (15)
1.式I的酞菁作为液体标记物的用途:
其中在式I中,
M为两个氢、两个锂、镁、锌、铜、镍、VO、TiO、AlCl、AlOCOCH3、AlOCOCF3、SiCl2或Si(OH)2,
R各自为选自-CH2-N(-X1-R1)(-X2-R2)和-CH2-Het的相同或不同的结构部分,
X1、X2各自独立地为羰基或化学单键,
R1为任选被1-4个醚官能氧原子间隔的C1-C20烷基,
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基取代的C5-C7环烷基,
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基取代的5或6元饱和杂环基团,
任选被一个或多个卤素、氰基、硝基、羟基、氨基、任选被1-4个醚官能氧原子间隔的C1-C20烷基、C1-C20烷氧基、C1-C20烷基氨基或C1-C20二烷基氨基取代的C6-C10芳基,
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基、C1-C20烷氧基、C1-C20烷基氨基或C1-C20二烷基氨基取代的含3-12个碳原子的杂芳基,
任选在芳基上被一个或多个卤素、氰基、硝基、羟基、氨基、任选被1-4个醚官能氧原子间隔的C1-C20烷基、C1-C20烷氧基、C1-C20烷基氨基或C1-C20二烷基氨基取代的C6-C10-芳基-C1-C4烷基,
或
在杂芳基中含3-12个碳原子的杂芳基-C1-C4烷基,所述杂芳基任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基、C1-C20烷氧基、C1-C20烷基氨基或C1-C20二烷基氨基取代,
R2为氢或独立于R1地如对R1所定义,且当X2为羰基时,R2不为氢,
Het为任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基取代且其中一个CH2基团任选被羰基替代的5、6或7元饱和杂环基团,
或
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C20烷基取代的含3-12个碳原子的杂芳基,
该饱和杂环基团或杂芳基经由合适的杂原子或碳原子键合于-CH2-Het结构部分的CH2基团上,
和
n在每种情况下独立地为0、1、2、3或4的值,条件是4个n值的总和至少为1。
2.根据权利要求1的用途,其中在式I中,
M为两个氢、两个锂、镁、锌、铜、镍、VO、TiO、AlCl、AlOCOCH3、AlOCOCF3、SiCl2或Si(OH)2,
R各自为相同或不同的-CH2-Het结构部分,
Het为任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代且其中一个CH2基团任选被羰基替代的5、6或7元饱和杂环,
或
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代的含3-5个碳原子的杂芳基,
该饱和杂环基团或杂芳基经由合适的杂原子或碳原子键合于-CH2-Het结构部分的CH2基团上,
和
n在每种情况下独立地为0、1或2的值,条件是4个n值的总和至少为1。
3.根据权利要求1的用途,其中在式I中,
M为两个氢、两个锂、镁、锌、铜、镍、VO、TiO、AlCl、AlOCOCH3、AlOCOCF3、SiCl2或Si(OH)2,
R为相同或不同的-CH2-Het结构部分,
Het为任选被一个或多个C1-C4烷基取代且其中一个CH2基团任选被羰基替代的5、6或7元饱和杂环基团,
或
任选被一个或多个C1-C4烷基取代的含3-5个碳原子的杂芳基,该饱和杂环基团或杂芳基经由合适的杂原子或碳原子键合于-CH2-Het结构部分的CH2基团上,
和
n在每种情况下独立地取0、1或2的值,条件是4个n值的总和至少为1。
4.根据权利要求1的用途,其中在式I中,
M为两个氢,
R为相同或不同的-CH2-Het结构部分,
Het为任选被一个或多个C1-C4烷基取代且其中与氮原子相邻的CH2基团被羰基替代的5、6或7元饱和含氮基团,
或
任选被一个或多个C1-C4烷基取代的含3-5个碳原子的含氮杂芳基,该饱和杂环基团或杂芳基经由合适的氮原子或碳原子键合于-CH2-Het结构部分的CH2基团上,
和
n在每种情况下独立地取0、1或2的值,条件是4个n值的总和至少为1。
5.根据权利要求1的用途,其中在式I中,
M为两个氢,
R为相同的-CH2-Het结构部分,
Het为任选被一个或多个C1-C4烷基取代且经由氮原子键合于-CH2-Het结构部分的CH2基团上的γ-丁内酰胺、δ-戊内酰胺或ε-己内酰胺基团,
和
n在每种情况下独立地取0、1或2的值,条件是4个n值的总和至少为1。
6.根据权利要求1的用途,其中在式I中,
M为两个氢、两个锂、镁、锌、铜、镍、VO、TiO、AlCl、AlOCOCH3、AlOCOCF3、SiCl2或Si(OH)2,
R各自为选自-CH2-N(-X1-R1)(-X2-R2)的相同或不同的结构部分,
X1、X2各自独立地为羰基或化学单键,
R1为任选被1-4个醚官能氧原子间隔的C1-C15烷基,
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代的环己基,
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代的5或6元饱和杂环基团,
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基、C1-C15烷氧基、C1-C15烷基氨基或C1-C15二烷基氨基取代的C6-C10芳基,任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基、C1-C15烷氧基、C1-C15烷基氨基或C1-C15二烷基氨基取代的含3-5个碳原子的杂芳基,
在芳基上任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基、C1-C15烷氧基、C1-C15烷基氨基或C1-C15二烷基氨基取代的苯基-C1-C4烷基,
或
在杂芳基中含3-5个碳原子的杂芳基-C1-C4烷基,所述杂芳基任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基、C1-C15烷氧基、C1-C15烷基氨基或C1-C15二烷基氨基取代,
R2为氢或独立于R1地如对R1所定义,且当X2为羰基时,R2不为氢,
和
n在每种情况下独立地取0、1或2的值,条件是4个n值的总和至少为1。
7.根据权利要求1的用途,其中在式I中,
M为两个氢,
R各自为选自-CH2-N(-X1-R1)(-X2-R2)的相同或不同的结构部分,
X1、X2各自独立地为羰基或化学单键,
R1为任选被1-4个醚官能氧原子间隔的C1-C15烷基,
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代的环己基,
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代的5或6元饱和杂环基团,
任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基、C1-C15烷氧基、C1-C15烷基氨基或C1-C15二烷基氨基取代的苯基,
或
在芳基上任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基、C1-C15烷氧基、C1-C15烷基氨基或C1-C15二烷基氨基取代的苯基-C1-C4烷基,
R2为氢或独立于R1地如对R1所定义,且当X2为羰基时,R2不为氢,
和
n在每种情况下独立地取0、1或2的值,条件是4个n值的总和至少为1。
8.根据权利要求1-7中任一项的式I的酞菁作为矿物油标记物的用途。
9.一种包含至少一种根据权利要求1-7中任一项的式I的酞菁作为标记物的液体。
10.一种包含至少一种根据权利要求1-7中任一项的式I的酞菁作为标记物的矿物油。
11.式Ia的酞菁:
其中在式Ia中,
M为两个氢、两个锂、镁、锌、铜、镍、VO、TiO、AlCl、AlOCOCH3、AlOCOCF3、SiCl2或Si(OH)2,
R各自为相同或不同的-CH2-Het结构部分,
Het为任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代且其中一个CH2基团任选被羰基替代的5、6或7元饱和杂环,
该饱和杂环基团经由合适的杂原子或碳原子键合于-CH2-Het结构部分的CH2基团上,
和
n在每种情况下独立地为0、1、2、3或4的值,条件是4个n值的总和至少为1。
12.根据权利要求11的酞菁,其中在式Ia中,
M为两个氢、两个锂、镁、锌、铜、镍、VO、TiO、AlCl、AlOCOCH3、AlOCOCF3、SiCl2或Si(OH)2,
R为相同或不同的-CH2-Het结构部分,
Het为任选被一个或多个任选被1-4个醚官能氧原子间隔的C1-C15烷基取代且其中一个CH2基团任选被羰基替代的5、6或7元饱和杂环基团,
该饱和杂环基团经由合适的杂原子或碳原子键合于-CH2-Het结构部分的CH2基团上,
和
n在每种情况下独立地为0、1或2的值,条件是4个n值的总和至少为1。
13.根据权利要求11的酞菁,其中在式Ia中,
M为两个氢、两个锂、镁、锌、铜、镍、VO、TiO、AlCl、AlOCOCH3、AlOCOCF3、SiCl2或Si(OH)2,
R为相同或不同的-CH2-Het结构部分,
Het为任选被一个或多个C1-C4烷基取代且其中一个CH2基团任选被羰基替代的5、6或7元饱和杂环基团,
该饱和杂环基团经由合适的杂原子或碳原子键合于-CH2-Het结构部分的CH2基团上,
和
n在每种情况下独立地为0、1或2的值,条件是4个n值的总和至少为1。
14.根据权利要求11的酞菁,其中在式Ia中,
M为两个氢,
R为相同或不同的-CH2-Het结构部分,
Het为任选被一个或多个C1-C4烷基取代且其中氮原子相邻的CH2基团任选被羰基替代的5、6或7元饱和杂环基团,
该饱和杂环基团经由合适的杂原子或碳原子键合于-CH2-Het结构部分的CH2基团上,
和
n在每种情况下独立地取0、1或2的值,条件是4个n值的总和至少为1。
15.根据权利要求11的酞菁,其中在式Ia中,
M为两个氢,
R为相同的-CH2-Het结构部分,
Het为任选被一个或多个C1-C4烷基取代且经由氮原子键合于-CH2-Het结构部分的CH2基团上的γ-丁内酰胺、δ-戊内酰胺或ε-己内酰胺基团,
和
n在每种情况下独立地为0、1或2的值,条件是4个n值的总和至少为1。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE102004003791A DE102004003791A1 (de) | 2004-01-23 | 2004-01-23 | Verwendung von Phthalocyaninen als Markierungsstoffe für Flüssigkeiten |
DE102004003791.4 | 2004-01-23 | ||
PCT/EP2005/000307 WO2005070935A1 (de) | 2004-01-23 | 2005-01-14 | Verwendung von phthalocyaninen als markierungsstoffe für flüssigkeiten |
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CN1910188A CN1910188A (zh) | 2007-02-07 |
CN1910188B true CN1910188B (zh) | 2010-10-13 |
Family
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AT (1) | ATE409701T1 (zh) |
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EA200801986A1 (ru) * | 2006-03-15 | 2009-02-27 | Басф Се | Применение арил- или алкоксизамещенных фталоцианинов в качестве маркирующих веществ для жидкостей |
CN109959626B (zh) * | 2019-04-08 | 2022-05-03 | 天津农学院 | 一种定量总脂含量的分光光度法及应用 |
WO2023241950A1 (en) | 2022-06-13 | 2023-12-21 | Basf Se | Mixtures of compounds having improved solubility for use as markers |
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GB949739A (en) * | 1961-06-20 | 1964-02-19 | Basf Ag | Non-flocculating phthalocyanine pigment mixtures fast to solvents |
WO1994002570A1 (de) * | 1992-07-23 | 1994-02-03 | Basf Aktiengesellschaft | Verwendung von im ir-bereich absorbierenden und/oder fluoreszierenden verbindugen als markierungsmittel für flüssigkeiten |
WO1998052950A1 (de) * | 1997-05-22 | 1998-11-26 | Basf Aktiengesellschaft | Phthalocyanine und ihre verwendung als markierungsmittel |
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JPS5444296A (en) * | 1977-09-14 | 1979-04-07 | Ibigawa Electric Ind Co Ltd | Abrasive for super precision finishing |
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GB8723258D0 (en) * | 1987-10-03 | 1987-11-04 | Ciba Geigy Ag | Dimethylaminomethyl copper phthalocyanine |
JPH0615671B2 (ja) * | 1987-10-20 | 1994-03-02 | 三井東圧化学株式会社 | 近赤外線吸収剤およびそれを用いた光記録媒体 |
JP2507786B2 (ja) * | 1988-07-29 | 1996-06-19 | 東洋インキ製造株式会社 | 光学記録媒体 |
EP0422907A2 (en) * | 1989-10-13 | 1991-04-17 | Toyo Ink Manufacturing Co., Ltd. | Copper phthalocyanine pigment composition and pigment composition dispersion containing same |
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JP3129030B2 (ja) * | 1993-06-04 | 2001-01-29 | 東洋インキ製造株式会社 | 銅フタロシアニン顔料組成物の製造方法 |
GB2328184B (en) | 1997-08-12 | 2001-10-17 | Alliedsignal Ltd | Vehicle sensor |
JP4139539B2 (ja) * | 2000-01-21 | 2008-08-27 | 富士フイルム株式会社 | 光重合性画像記録材料及び平版印刷版原版 |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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GB949739A (en) * | 1961-06-20 | 1964-02-19 | Basf Ag | Non-flocculating phthalocyanine pigment mixtures fast to solvents |
WO1994002570A1 (de) * | 1992-07-23 | 1994-02-03 | Basf Aktiengesellschaft | Verwendung von im ir-bereich absorbierenden und/oder fluoreszierenden verbindugen als markierungsmittel für flüssigkeiten |
WO1998052950A1 (de) * | 1997-05-22 | 1998-11-26 | Basf Aktiengesellschaft | Phthalocyanine und ihre verwendung als markierungsmittel |
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AR049677A1 (es) | 2006-08-30 |
DE102004003791A1 (de) | 2005-08-11 |
US7767807B2 (en) | 2010-08-03 |
PL1713811T3 (pl) | 2009-04-30 |
US20080227973A1 (en) | 2008-09-18 |
EP1713811A1 (de) | 2006-10-25 |
CA2554132A1 (en) | 2005-08-04 |
MY141719A (en) | 2010-06-15 |
WO2005070935A1 (de) | 2005-08-04 |
DK1713811T3 (da) | 2009-02-02 |
TW200600550A (en) | 2006-01-01 |
CN1910188A (zh) | 2007-02-07 |
IL176638A0 (en) | 2006-10-31 |
JP4571951B2 (ja) | 2010-10-27 |
PE20051103A1 (es) | 2006-01-31 |
ES2311962T3 (es) | 2009-02-16 |
NO20063091L (no) | 2006-10-20 |
MXPA06007648A (es) | 2006-09-01 |
PT1713811E (pt) | 2008-10-27 |
JP2007518857A (ja) | 2007-07-12 |
NZ548491A (en) | 2009-05-31 |
EP1713811B1 (de) | 2008-10-01 |
BRPI0506952A (pt) | 2007-07-03 |
KR20060131847A (ko) | 2006-12-20 |
ATE409701T1 (de) | 2008-10-15 |
DE502005005529D1 (de) | 2008-11-13 |
ZA200606943B (en) | 2008-04-30 |
AU2005206266A1 (en) | 2005-08-04 |
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