CN1080291C - 1,4-二酮吡咯并吡咯的混晶和固溶体的制备方法 - Google Patents
1,4-二酮吡咯并吡咯的混晶和固溶体的制备方法 Download PDFInfo
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- CN1080291C CN1080291C CN96122507A CN96122507A CN1080291C CN 1080291 C CN1080291 C CN 1080291C CN 96122507 A CN96122507 A CN 96122507A CN 96122507 A CN96122507 A CN 96122507A CN 1080291 C CN1080291 C CN 1080291C
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- 125000001400 nonyl 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])[H] 0.000 description 1
- BPYXFMVJXTUYRV-UHFFFAOYSA-J octanoate;zirconium(4+) Chemical compound [Zr+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O BPYXFMVJXTUYRV-UHFFFAOYSA-J 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- 229920001568 phenolic resin Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000005060 rubber Substances 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
- 238000000926 separation method Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000009987 spinning Methods 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
- 239000000758 substrate Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 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
- 238000007669 thermal treatment Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
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- 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
- C07D487/02—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 two hetero rings
- C07D487/04—Ortho-condensed systems
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
- C09B67/0039—Mixtures of diketopyrrolopyrroles
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Abstract
本发明涉及通过将固态的相应混合物加热至220-380℃范围内的温度制备由两种不同的下式(I)化合物(式中A和B的定义见说明书)各1mol构成的1,4-二酮吡咯并[3,4-c]吡咯的混晶的方法。所获得的混晶和固溶体极佳地适用于将高分子材料着色。
Description
本发明涉及由两种不同的对称1,4-二酮吡咯并吡咯通过将相应的混合物加热至高温制备混晶和固溶体的方法。
美国专利第4783540号披露固溶体可通过将两种不同的1,4-二酮吡咯并吡咯最好按65-90∶35-10%(重量)的比率混合随后按下述对其进行处理获得:-使与极性有机溶剂接触,最好在回流温度搅拌该组分混合物,-使该组分混合物在极性有机溶剂中碱沉,或者将该组分混合物在极性有机溶剂中在碱金属醇化物、碱金属氢氧化物或季铵化合物存在下搅拌,-酸沉,即将该组分混合物溶于酸中并通过用水稀释使固溶体沉淀,或者-充分研磨或捏合该组分混合物,其中要求随后在水和/或有机溶剂中重结晶。
这些固溶体的特点在于其X射线衍射图,而且固溶体的X射线衍射图与各组分的X射线衍射图的总和不同。
现已发现仅将两种不同的固态1,4-二酮吡咯并吡咯的混合物加热就能令人惊异地获得混晶或固溶体。
关于固溶体和混晶的定义,为避免误解,这里应当注意:根据组分的结构和混合比率,用本发明方法可能获得两类产物:-“主-客”型固溶体,其中“容”组分进入“主”的晶格中。这样的固溶体的X射线衍射图包含“主”组分的线。若在X射线衍射图中未出现“客”组分的线,则该产物是晶体学纯的,也就是说,它是单相固溶体;-混晶,其中形成全新的晶格。所述混晶的X射线衍射图与各组分的X射线衍射图不同。
因此,本发明涉及由两种不同的下式(I)化合物构成的1,4-二酮吡咯并[3,4-c]吡咯的混晶或固溶体的制备方法:式中A和B相互独立地为下式基团: 或
式中R1和R2相互独立地为氢,卤素,C1-C18烷基,C1-C18烷氧基,C1-C18
烷基巯基,C1-C18烷基氨基,C2-C18烷氧基羰基,C2-C18烷基氨
基羰基,-CN,-NO2,苯基,三氟甲基,C5-C6环烷基,-C=N-(C1-C18
吡咯基,噁唑基,苯并噁唑基,苯并噻唑基,苯并咪唑基,吗啉基,
哌啶基或吡咯烷基,G 是-CH2-,-CH(CH3)-,-C(CH3)2-,-CH=N-,-N=N-,-O-,-S-,-SO-,
-SO2-,-CONH-或-NR7-,R3和R4相互独立地为氢,卤素,C1-C6烷基,C1-C18烷氧基或-CN,R5和R6相互独立地为氢,卤素或C1-C6烷基,和R7是氢或C1-C6烷基;该方法包括将式(I)的两种不同的固态化合物加热至220-380℃范围内的温度,优选240-360℃,更优选270-340℃。
被定义为卤素的取代基一般是碘、氟,优选溴,更优选氯,
C1-C6烷基一般是甲基,乙基,正丙基,异丙基,正丁基,仲丁基,叔丁基,正戊基,叔戊基,己基,和C1-C18烷基一般另外还是庚基,辛基,2-乙基己基,壬基,癸基,十二烷基,十四烷基,十六烷基或十八烷基;
C1-C18烷氧基以及在C2-C18烷氧基羰基中的烷氧基一般是甲氧基,乙氧基,正丙氧基,异丙氧基,丁氧基,己氧基,癸氧基,十二烷氧基,十六烷氧基或十八烷氧基;
C1-C18烷基巯基是例如甲基巯基,乙基巯基,丙基巯基,丁基巯基,辛基巯基,癸基巯基,十六烷基巯基或十八烷基巯基;
C1-C18烷基氨基以及在C2-C18烷基氨基羰基中的烷基氨基一般是甲基氨基,乙基氨基,丙基氨基,己基氨基,癸基氨基,十六烷基氨基或十八烷基氨基;
C5-C6环烷基一般是环戊基,最好是环己基。
C6烷基氨基,CN或苯基,G 是-O-,-NR7-,-N=N-或-SO2-,R3和R4为氢,和R7是氢,甲基或乙基;本发明方法对于制备式(I)中的A和B为下式基团的混晶更特别有意义:式中R1和R2相互独立地为氢,甲基,叔丁基,氯,溴,苯基或CN,R2最好是氢。
两种不同的式(I)组分通常以50-95%∶50-5%、最好是50-60∶50-40%的摩尔比存在,导致混晶或固溶体与起始产物相比在色泽上产生有意义的变化。
这两个组分之一本身可以是两种不同的式(I)化合物的混合物。
本发明的混晶的制备宜这样进行:将上面定义的不同的式(I)组分用通常已知的方法紧密混合并进行下述处理:-将该组分混合物例如在烘箱中加热至上述所要求的温度,或者-使该组分混合物在升华设备中升华(尤其是按在J.Mizuguchi,Crystal Research and Technology,16,695-700(1981)中所述)。
在后一种情况下,在由气相冷凝的过程中形成纯的混晶。然而务必在整个长冷凝区保持略低于起始物质的升华点的高温,使其恒定。该长冷凝区能将混晶与在比混晶低的温度冷凝的未反应的起始物分离。
本发明的另一个实施方案包括将两种不同的组分通过在高真空下单独蒸发以两个或更多个交替薄层涂布在适宜的基底(例如玻璃或耐热聚合物)上,然后对其涂布光敏聚合物保护层(例如UV可交联的丙烯酸酯基漆DAICURE CLEAR SD-17(DIC GmbH);基于丙烯酸酯的UV硬化漆RENGOLUX Rz 3203/001无色(Dr.Renger GmbH)),和随后用激光例如用Ar+激光(λ=514nm)照射它们。
形成固态混晶。
后一个方法极适用于光学记录操作。
为使该两组分的混合容易进行,可以加入混合助剂,一般是NaCl,最好是NaF。混合助剂的加入量通常为该组分混合物的0-20%(重量),最好是0.5-2%(重量)。
为使该颜料的性质达到最佳,对该颜料进行后处理可能是适宜的。采用颜料用常规方法进行重结晶或热处理。常用的方法是在水或有机溶剂中并在常压或加压下进行热后处理。最好使用有机溶剂,一般是被卤原子、烷基或硝基取代的苯,例如二甲苯,氯苯,邻二氯苯或硝基苯,以及吡啶碱类,一般是吡啶,甲基吡啶或喹啉,还可以使用酮类,例如环己酮,醇类,例如异丙醇、丁醇、或戊醇,醚类,例如2-甲氧基乙醇或2-乙氧基乙醇,酰胺类,例如二甲基甲酰胺或N-甲基吡咯烷酮,以及二甲亚砜或四氢噻吩砜。后处理还可以在水中在常压或加压下在有机溶剂存在和/或加入表面活性剂的条件下进行。
可以使用本发明方法的混晶以及固溶体作为将高分子量有机材料着色用颜料。
可用该新混晶或固溶体着色的高分子有机材料的例证性实例是纤维素醚和酯,一般是乙基纤维素、硝基纤维素、乙酸纤维素、丁酸纤维素,天然树脂或合成树脂,一般是聚合或缩合树脂,例如氨基塑料,最好是脲/甲醛和三聚氰胺/甲醛树脂,醇酸树脂,酚醛塑料,聚碳酸酯,聚烯烃,聚苯乙烯,聚氯乙烯,聚酰胺,聚氨酯,聚酯,ABS,聚苯醚,橡胶,酪素,硅氧烷和有机硅树脂,它们可单独使用或以混合物的形式使用。
上述高分子有机化合物可以单独或者作为塑料、熔体或以纺丝溶液、油漆、涂料或印刷油墨的形式存在的混合物获得。根据使用要求,宜使用本发明的混晶或固溶体作为有机颜料或者以制剂形式使用。
本发明的混晶或固溶体可以待着色高分子有机材料的0.01-30%(重量)、最好是0.1-10%(重量)的量来使用。
用本发明的混晶或固溶体使高分子有机材料着色宜通过将这样的混晶或固溶体本身或以母料形式用辊式研磨机、混合或研磨设备掺入基料中来实施。然后将经染色的材料用本身已知的方法制成期望的最终形式,宜采用压延、模塑、挤塑、涂布、铸塑或注塑方法。为制备非脆性模制品或者降低它们的脆性,在加工前将增塑剂掺入至该高分子化合物中常常是合乎需要的。适宜的增塑剂一般是磷酸、苯二甲酸或癸二酸的酯。增塑剂可在将该颜料掺入聚合物中之前或之后掺入该新的混晶或固溶体中。为获得不同的色泽,除该新的混晶或固溶体外,还可以以任何量添加高分子有机材料填充剂或其它的发色成分例如白色的、有色的或黑色的颜料。
就将油漆、涂料和印刷油墨着色而言,将所述高分子有机材料和本发明的混晶或固溶体连同可任选的添加剂例如填充剂、其它的颜料、干燥剂或增塑剂一起细分散于或者溶于普通的有机溶剂或溶剂混合物中。该步骤可以这样实施:将各组分或者也可以将几种组分共同分散于或溶于溶剂中,然后将所有组分混合。
所述新的混晶和固溶体特别适用于将塑料、尤其是聚氯乙烯和聚烯烃和油漆、最好是汽车用大漆着色。
然而,混晶或固溶体还可以通过将两种吡咯并吡咯组分单独掺入聚合物中并将该混合物加热至适宜的温度而在该聚合物中形成。因此,本发明的另一个实施方案包括将两种不同的式(I)化合物与聚合物一起在挤塑机中于160-210℃范围内的温度分散,然后将它们在220-300℃范围内的温度模塑。如此获得的塑料模制品被在挤塑机中生成的混晶(或固溶体)着色。混晶通常在聚合物中在至少220-300℃范围内的温度生成。
适用于该目的的聚合物是例如聚碳酸酯,聚烯烃,聚苯乙烯,聚酰胺,聚酯,ABS或聚苯醚。
当用于使例如聚氯乙烯或聚烯烃着色时,该新的混晶以及新的固溶体具有良好的全面的颜料性能例如良好的分散性,优良的色强度和纯度,良好的耐渗移、耐热、耐目光和耐气候牢度,以及良好的遮盖力。
下列实施例将更详细地说明本发明。实施例1将2.36g(6.6mmol)下式吡咯并吡咯2.09g(6.6mmol)式吡咯并吡咯
和40mg氟化钠在研钵中紧密混合。将如此获得的粉末状混合物置于带有封闭式盖的瓷皿中并在烘箱中加热至300℃4小时,以定量收率获得红色的粉末状产物,将其用水充分洗涤,然后在真空干燥箱中于80℃干燥。分析: C H N Cl计算值: 67.76% 3.89% 8.32% 10.53%实测值: 67.19% 3.86% 8.27% 10.51%X射线衍射图的特点在于具有下列衍射线:
面间距 散射角 相对强度
(d值,) (2)
15.1550 5.83 100
6.8411 12.93 29
6.4135 13.80 24
6.0442 14.64 41
5.0401 17.58 18
3.7190 23.91 24
3.6148 24.61 14
3.3203 26.83 86
3.1550 28.26 27
2.8766 31.06 14
2.7846 32.12 9
实施例2
将0.9g(2.5mmol)式(II)吡咯并吡咯(见实施例1)、1.0g(2.2mmol)下式吡咯并吡咯和10mg氟化钠在研钵中紧密混合。将如此获得的粉末状混合物置于带有封闭式盖的瓷皿中并在烘箱中加热至270℃ 1小时,以定量收率获得带蓝色的红色粉末状产物,将其用水充分洗涤,然后在真空干燥箱中于80℃干燥。分析: C H N Cl计算值: 69.25% 4.94% 7.42% 9.93%实测值: 69.15% 5.10% 7.23% 9.54%X射线衍射图的特点在于具有下列衍射线:
面间距 散射角 相对强度
(d值,) (2)
19.4419 4.54 100
9.5816 9.22 8
6.3592 13.52 23
4.9987 17.73 64
4.8998 18.09 37
3.7966 23.41 9
3.6459 24.40 10
3.3709 26.42 56
3.2363 27.54 18
3.1617 28.20 11
3.0412 29.34 10
实施例3
将5.36g(15mmol)式(II)吡咯并吡咯(见实施例1)和4.01g(10mmol)式(IV)吡咯并吡咯(见实施例2)在研钵中紧密混合。将如此获得的粉末状混合物置于带有封闭式盖的瓷皿中并在烘箱中加热至300℃4小时,以定量收率获得带蓝色的红色粉末状产物。分析: C H N Cl计算值: 67.51% 4.51% 7.51% 11.91%实测值: 67.53% 4.62% 7.24% 11.31%X射线衍射图的特点在于具有下列衍射线:
面间距 散射角 相对强度
(d值,) (2)
19.1018 4.62 100
15.8733 5.56 8
6.3224 14.00 20
4.9820 17.79 42
4.8891 18.13 27
3.7810 23.51 9
3.6309 24.50 9
3.4538 25.77 9
3.3589 26.52 39
3.2236 27.65 14
3.1532 29.34 18
3.0371 29.39 8
实施例4
将7.5g实施例1的混晶、98.9g CAB溶液、36.5g聚酯树脂DYNAPOL H700(Dynamit Nobel)、4.6g三聚氰胺树脂MAPRENALMF650(Hoechst)和2.5g分散剂DISPERBYK160(Byk Chemie)一起在分散混合器中分散90分钟(总漆量:150g;5%的颜料);所述CAB溶液由41.0g乙酰丁酸纤维素(CAB531.1,20%,在丁醇/二甲苯2∶1中)(Eastman Chem)、1.5g辛酸锆、18.5gSOLVESSO 150(SOLVESSO:芳烃;ESSO)、21.5g乙酸丁酯和17.5g二甲苯组成。
关于底涂层,将27.69g如此获得的主色漆(mass-tone varnish)与17.31g Al储液(8%)混合并喷至铝板上(湿膜c.20μm);所述Al储液由12.65gSILBERLINE SS 3334AR,60%(Sillberline Ltd.)、56.33g CAB溶液(组成如上)、20.81g聚酯树脂DYNAPOL H700、2.60g三聚氰胺树脂MAPRENAL MF650和7.59gSOLVESSO 150组成。于室温在空气中干燥30分钟后,将TSA漆作为罩面漆喷至其上(湿膜c.50μm);所述TSA漆由29.60g丙烯酸类树脂URACRON 2263 XB,(50%,在二甲苯/丁醇中)(Chem.Fabrik Schweizerhalle)、5.80g三聚氰胺树脂CYMEL 327(90%,在异丁醇中)、2.75g丁基乙二醇乙酸酯、5.70g二甲苯、1.65g正丁醇、0.50g硅氧烷油(1%,在二甲苯中)、3.00g抗光剂TINUVIN 900(10%,在二甲苯中)(Ciba)和1.00g抗光剂TINUVIN292(10%,在二甲苯中)(Ciba)组成。于室温在空气中再干燥30分钟后,将该漆于130℃烘30分钟。
实施例5
将0.6g实施例1的混晶与67g聚氯乙烯、33g邻苯二甲酸二辛酯、2g二月桂酸二丁锡和2g二氧化钛混合并在辊式研磨机上于160℃处理15分钟使成薄膜。如此获得的PVC膜具有较佳的色强度并耐渗移和光。
实施例6
将1000g聚丙烯颗粒(DAPLEN PT-55,Chemie LINZ)和20g由10g实施例3的固溶体和10g山嵛酸镁组成的50%的颜料制剂在混合鼓中充分混合。然后将如此处理的颗粒按照熔融抽丝法在260至285℃范围内的温度抽丝,获得具有极佳的耐光牢度和织物牢度性能的红色长丝。实施例7将0.5g(1.7mmol)下式吡咯并吡咯和0.7g(1.7mmol)式(IV)吡咯并吡咯(见实施例2)紧密混合并置于由钽构成的蒸发舟皿中。然后将该舟皿放入升华管中,然后用装有冷阱的旋片式机械真空泵蒸发。接着,将氩载气以0.15ml/分钟的氩流速引入升华管中,并于340℃进行升华24小时。在310℃温度区冷凝出一种暗红色的物质,为晶状粉末(1.08g,收率90%)。根据光谱和晶体学分析,该产物实质上与实施例1的产物相同。未反应的原料在较低温度区冷凝,因而可以容易地将其分离。
实施例8
使用装有两个可以被单独控制的蒸发舟皿的真空蒸发设备制备多层体系。将式(V)吡咯并吡咯(见实施例7)第一层(150)和式(IV)吡咯并吡咯(见实施例2)第二层(亦是150)通过在高真空下依次蒸发涂布在玻璃盘上,两种产品按1∶1的摩尔比使用。将该操作重复3次,每次均在真空下,因而通过蒸发在该玻璃盘上交替涂布四对薄层。随后将由UV可交联的丙烯酸酯基漆(DAICURE CLEAR SD-17;DICGmbH)构成的保护层(层厚度为大约10μm)涂布至其上并用UV光交联。然后将用这种方式涂布的玻璃盘用Ar+激光(λ=514nm;400mW)以100mm/秒的扫描速率照射。照射导致色泽立即由红色变为暗红色。在494和576nm具有两个吸收峰的吸收光谱基本上与实施例1混晶的一致。
该多层体系极佳地适用于一次写入式光盘。
实施例9
将0.5g式(IV)吡咯并吡咯(见实施例2)和0.5g式(V)吡咯并吡咯(见实施例7)、1.0g抗氧化剂(IRGANOX)1010、CIBA-GEIGY AG)和1000g聚乙烯-HD颗粒(VESTOLEN 60-16,HUELS)的混合物在玻璃烧瓶中在滚子齿齿轮摇床上预混合15分钟。然后将混合物在单螺杆挤塑机中在160至200℃的温度范围以两个通道挤塑。将如此获得的颗粒在注塑机(FERROMATIK AARBURG 200)中于240℃模塑5分钟制板。
获得暗红色的板,该颜色与用相应的混晶着色的聚乙烯板的颜色相同。
实施例10
重复实施例9的操作,只是用相同量的式(II)吡咯并吡咯(见实施例1)代替式(V)吡咯并吡咯。获得暗红色的板,该颜色与用相应的混晶着色的聚乙烯板的颜色完全一致。
实施例11
重复实施例9的操作,只是用相同量的式(II)吡咯并吡咯(见实施例1)代替式(IV)吡咯并吡咯并用相同量的下式吡咯并吡咯代替式(V)吡咯并吡咯,而且注塑在280℃进行。获得红色的板,该颜色与用相应的混晶着色的板的颜色相同。
实施例12
Claims (10)
1.制备由两种不同的下式(I)化合物构成的1,4-二酮吡咯并[3,4-c]吡咯的混晶或固溶体的方法:式中A和B相互独立地为下式基团: 或
式中R1和R2相互独立地为氢,卤素,C1-C18烷基,C1-C18烷氧基,C1-C18
烷基巯基,C1-C18烷基氨基,C2-C18烷氧基羰基,C2-C18烷基氨
基羰基,-CN,-NO2,苯基,三氟甲基,C5-C6环烷基,-C=N-(C1-C18烷基),
,咪唑基,吡唑基,三唑基,哌嗪基,
吡咯基,噁唑基,苯并噁唑基,苯并噻唑基,苯并咪唑基,吗啉基,
哌啶基或吡咯烷基,G是-CH2-,-CH(CH3)-,-C(CH3)2-,-CH=N-,-N=N-,-O-,-S-,-SO-,
-SO2-,-CONH-或-NR7-,R3和R4相互独立地为氢,卤素,C1-C6烷基,C1-C18烷氧基或-CN,R5和R6相互独立地为氢,卤素或C1-C6烷基,和R7是氢或C1-C6烷基;该方法包括将式(I)的两种不同的固态化合物的混合物加热至220-380℃范围内的温度。
4.按照权利要求3的方法,其中式(I)中的R2是氢。
5.按照权利要求1的方法,其中两种不同的式(I)组分以50-95%:50-5%的摩尔比存在。
6.按照权利要求1的方法,它包括将所述两种不同的组分加热至270-340℃范围内的温度。
7.按照权利要求1的方法,它包括将所述不同的式(I)组分用常规方法紧密混合并将其加热至220-380℃范围内的温度。
8.按照权利要求1的方法,它还包括将所述不同的式(I)化合物用常规方法紧密混合并使如此获得的化合物混合物通过恒定的高温范围在升华设备中升华,所述恒定的高温范围稍低于原料物质的升华点但足以使式I化合物冷凝。
9.按照权利要求1的方法,它还包括将所述不同的式(I)化合物通过在高真空下单独蒸发以两个或更多个交替薄层涂布在玻璃或耐热聚合物上,然后对其涂布光敏聚合物保护层UV-可交联的丙烯酸酯基清漆或UV-硬化的基于丙烯酸酯的清漆和随后用激光照射它们,所述高真空足以蒸发式I的两种化合物。
10.按照权利要求1的方法,它还包括将两种不同的式(I)化合物与聚合物一起在挤塑机中在160-210℃范围内的温度分散,然后将它们在220-300℃范围内的温度模塑成模制品。
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CH265195 | 1995-09-20 | ||
CH2651/95 | 1995-09-20 |
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CN1080291C true CN1080291C (zh) | 2002-03-06 |
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US (2) | US5693824A (zh) |
EP (1) | EP0764696B1 (zh) |
JP (1) | JPH09124649A (zh) |
KR (1) | KR100451601B1 (zh) |
CN (1) | CN1080291C (zh) |
CA (1) | CA2185875A1 (zh) |
DE (1) | DE59609208D1 (zh) |
TW (1) | TW341572B (zh) |
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EP0877058B1 (de) * | 1997-05-06 | 2002-07-03 | Ciba SC Holding AG | Diketopyrrolopyrrolzusammensetzungen |
US20020194084A1 (en) * | 1997-11-14 | 2002-12-19 | Anita Surles | Method and use of point-of sale terminal, which receives, transmits, stores, authorizes, reconciles, and calculates transactions electronically |
EP0952183B1 (de) | 1998-04-22 | 2005-02-23 | Ciba SC Holding AG | Verzugsfreie Pigmentzusammensetzungen enthaltend Diaryl-diketopyrrolo 3,4c pyrrole |
US6375732B1 (en) | 1999-04-08 | 2002-04-23 | Clariant Finance (Bvi) Limited | Pigments, the process of their manufacturing and their use |
CA2374977A1 (en) * | 1999-07-09 | 2001-01-18 | Ciba Specialty Chemicals Holding Inc. | Pigments having improved colouristic properties and process for their preparation |
DE60003508T2 (de) | 1999-11-17 | 2004-04-29 | Ciba Speciality Chemicals Holding Inc. | Diketopyrrolopyrrol |
DE10028104A1 (de) | 2000-06-07 | 2001-12-13 | Clariant Gmbh | Verfahren zur Herstellung von Diketopyrrologyrrol-Pigmenten |
EP1387870B1 (en) * | 2001-05-14 | 2005-11-23 | Ciba SC Holding AG | New crystal modification of diketopyrrolpyrrole solid solution pigment |
US20050008892A1 (en) * | 2002-02-01 | 2005-01-13 | Hiroshi Yamamoto | Fluorescent compositions comprising diketopyrrolopyrroles |
EP1641802A2 (en) * | 2003-07-07 | 2006-04-05 | Ciba SC Holding AG | Process for the preparation of furopyrroles |
EP1731576B1 (en) * | 2005-02-22 | 2010-05-12 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Diketopyrrolopyrrole Pigment dispersants and their use |
WO2008000664A1 (en) * | 2006-06-30 | 2008-01-03 | Ciba Holding Inc. | Diketopyrrolopyrrole polymers as organic semiconductors |
US20100009214A1 (en) * | 2006-10-06 | 2010-01-14 | Takeshi Sato | Alpha-diketopyrrolopyrrole pigment, coloring composition containing the same, and red film |
DE102007049883A1 (de) * | 2007-10-18 | 2009-04-23 | Clariant International Ltd. | Diketopyrrolopyrrol-Mischkristalle |
WO2009144115A1 (en) | 2008-05-28 | 2009-12-03 | Basf Se | Improved, red colour filter composition |
CN110791118A (zh) * | 2018-08-01 | 2020-02-14 | 浙江浩川科技有限公司 | 吡咯并吡咯二酮类颜料衍生物合成方法及其制成产品用途 |
CN110790995A (zh) * | 2018-08-01 | 2020-02-14 | 浙江浩川科技有限公司 | 一种具有抗翘曲性能的聚烯烃色母粒及其制备方法 |
CN110791117A (zh) * | 2018-08-01 | 2020-02-14 | 浙江浩川科技有限公司 | 一种芳香亚胺基取代的dpp类有机颜料及合成方法和用途 |
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EP0348889B1 (en) * | 1988-06-27 | 1995-12-13 | Mitsubishi Chemical Corporation | Photoconductive material and process for producing the same |
DE58909667D1 (de) * | 1988-07-29 | 1996-05-30 | Riedel De Haen Ag | Optische datenspeicher |
KR0143777B1 (ko) * | 1989-11-28 | 1998-07-01 | 월터 클리웨인, 한스-피터 위트린 | 디케토피롤로피롤을 기재로 하는 물질의 조성물 |
JPH04372632A (ja) * | 1991-06-21 | 1992-12-25 | Nippon Kayaku Co Ltd | ポリオレフィン系樹脂用着色剤及びそれにより着色されたポリオレフィン系樹脂着色物 |
EP0654506B1 (de) * | 1993-11-22 | 2000-05-17 | Ciba SC Holding AG | Verfahren zur Herstellung synergistischer Pigmentgemische |
EP0704497B1 (de) * | 1994-09-28 | 1999-12-15 | Ciba SC Holding AG | Mischkristalle und feste Lösungen von 1,4-Diketopyrrolopyrrolen |
TW434296B (en) * | 1994-10-12 | 2001-05-16 | Ciba Sc Holding Ag | Process for the preparation of diaryldiketopyrrolopyrrole pigments |
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1996
- 1996-09-03 TW TW085110721A patent/TW341572B/zh active
- 1996-09-11 DE DE59609208T patent/DE59609208D1/de not_active Expired - Fee Related
- 1996-09-11 EP EP96810602A patent/EP0764696B1/de not_active Expired - Lifetime
- 1996-09-12 US US08/712,721 patent/US5693824A/en not_active Expired - Fee Related
- 1996-09-18 CA CA002185875A patent/CA2185875A1/en not_active Abandoned
- 1996-09-19 KR KR1019960040950A patent/KR100451601B1/ko not_active IP Right Cessation
- 1996-09-19 CN CN96122507A patent/CN1080291C/zh not_active Expired - Fee Related
- 1996-09-20 JP JP8248430A patent/JPH09124649A/ja not_active Withdrawn
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EP0764696A3 (de) | 1998-04-01 |
TW341572B (en) | 1998-10-01 |
JPH09124649A (ja) | 1997-05-13 |
EP0764696B1 (de) | 2002-05-15 |
KR100451601B1 (ko) | 2005-04-13 |
CA2185875A1 (en) | 1997-03-21 |
CN1158875A (zh) | 1997-09-10 |
EP0764696A2 (de) | 1997-03-26 |
US5808094A (en) | 1998-09-15 |
KR970015591A (ko) | 1997-04-28 |
DE59609208D1 (de) | 2002-06-20 |
US5693824A (en) | 1997-12-02 |
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