CN1076369C - 1,4——二酮吡咯并吡咯的固溶体 - Google Patents
1,4——二酮吡咯并吡咯的固溶体 Download PDFInfo
- Publication number
- CN1076369C CN1076369C CN96122501A CN96122501A CN1076369C CN 1076369 C CN1076369 C CN 1076369C CN 96122501 A CN96122501 A CN 96122501A CN 96122501 A CN96122501 A CN 96122501A CN 1076369 C CN1076369 C CN 1076369C
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- CN
- China
- Prior art keywords
- formula
- alkyl
- sosoloid
- hydrogen
- pyrrolopyrrole
- 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.)
- Expired - Fee Related
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- 239000006104 solid solution Substances 0.000 title abstract description 4
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000011368 organic material Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 39
- -1 pyrryl Chemical group 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 239000000843 powder Substances 0.000 claims description 18
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 229920002521 macromolecule Polymers 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000002170 ethers Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 230000005540 biological transmission Effects 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 150000001243 acetic acids Chemical class 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- YLGDYASRRVBIRS-UHFFFAOYSA-N 1,4-bis(4-phenylphenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C=12C(=O)NC(C=3C=CC(=CC=3)C=3C=CC=CC=3)=C2C(=O)NC=1C(C=C1)=CC=C1C1=CC=CC=C1 YLGDYASRRVBIRS-UHFFFAOYSA-N 0.000 abstract 1
- 230000000485 pigmenting effect Effects 0.000 abstract 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N 1-Pyrroline Chemical compound C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- 239000000049 pigment Substances 0.000 description 15
- 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 14
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 14
- 229910052700 potassium Inorganic materials 0.000 description 14
- 239000011591 potassium Substances 0.000 description 14
- 229910052708 sodium Inorganic materials 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- 238000001291 vacuum drying Methods 0.000 description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 229910052744 lithium Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical class CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 239000004800 polyvinyl chloride Substances 0.000 description 5
- 229920000915 polyvinyl chloride Polymers 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000004902 Softening Agent Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000004922 lacquer Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- XPZQBGDNVOHQIS-UHFFFAOYSA-N 2,9-dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(Cl)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)Cl)N1)C1=C2 XPZQBGDNVOHQIS-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- 239000004640 Melamine resin Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
- 239000003495 polar organic solvent Substances 0.000 description 3
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- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 3
- 238000007669 thermal treatment Methods 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical class CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
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- TXWSZJSDZKWQAU-UHFFFAOYSA-N 2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(C)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)C)N1)C1=C2 TXWSZJSDZKWQAU-UHFFFAOYSA-N 0.000 description 2
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- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
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- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical class [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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- 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
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Classifications
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- C—CHEMISTRY; METALLURGY
- 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
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- 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
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Cosmetics (AREA)
Abstract
本发明涉及由式(Ⅰ)吡咯并吡咯和a)式(Ⅱ)吡咯并吡咯或b)式(Ⅲ)喹吖啶酮以(Ⅰ)∶(Ⅱ)或(Ⅰ)∶(Ⅲ)为20-90%(重量):80-10%(重量)的相应比率构成的固溶体;所述式(Ⅱ)和(Ⅲ)中的A、B和R8的定义见说明书。该新固溶体非常适宜将高分子有机材料着色。
Description
本发明涉及3,6-双(联苯-4-基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮和喹吖啶酮或另一种吡咯并吡咯的新的单相固溶体、其制备方法及其作为颜料的用途。
由美国专利第4783540和4810304号中得知,当将两种不同的1,4-二酮吡咯并吡咯混合或者将1,4-二酮吡咯并吡咯与喹吖啶酮混合,随后通过捏合、研磨或再沉淀时,可获得固溶体。固溶体的特点在于其X射线衍射图,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。然而现已确定:在这些专利中所述的产物是多相固溶体;换句话说,相应的X射线衍射图不仅显示出固溶体的新线,而且还显示出一种和/或另一种单一组分的线。
现已令人惊异地发现:在3,6-双(联苯-4-基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮(在前述的专利文献中称作1,4-二酮-3,6-双(联苯-4-基)吡咯并[3,4-c]吡咯)存在下,其它的吡咯并吡咯和喹吖啶酮作为客体落在其晶格(主体晶格)中形成单相固溶体。因此,所获得的固溶体具有与3,6-双(联苯-4-基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮相同的晶格,并且相应的X射线衍射图实质上是相同的。
通过形成这样的固溶体,在具有极大意义的色泽方面可以获得非常有利的改变,而对已经有的3,6-双(联苯-4-基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮的良好的颜料性能无不利影响。
因此,本发明涉及由式(I)吡咯并吡咯和a)式(II)吡咯并吡咯或b)式(III)喹吖啶酮以(I)∶(II)或(I)∶(III)为20-90%(重量)∶80-10%(重量)的相应比率构成的固溶体;所述式(I)如下:所述式(II)如下:式中A和B相互独立地为下式基团: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,C1-C18烷氧基羰基,C1-C18烷基氨
基羰基,-CN,-NO2,三氟甲基,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;所述式(III)如下:式中R8为氢,卤素,C1-C6烷基或C1-C6烷氧基。
任何卤素取代基是例如碘、氟,尤其是溴,优选氯;
C1-C6烷基的实例是甲基,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,在C1-C18烷基的情况下还有例如庚基,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烷氧基或在C1-C18烷氧基羰基中的C1-C18烷氧基,对于C1-C6烷氧基,是例如甲氧基,乙氧基,正丙氧基,异丙氧基,丁氧基,己氧基,还有癸氧基,十二烷氧基,十六烷氧基或十八烷氧基;
C1-C18烷基巯基的实例是甲基巯基,乙基巯基,丙基巯基,丁基巯基,辛基巯基,癸基巯基,十六烷基巯基和十八烷基巯基;
C1-C18烷基氨基或在C1-C18烷基氨基羰基中的C1-C18烷基氨基是例如甲基氨基,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环烷基是例如环戊基,特别是环己基。
C6烷基氨基或CN,G是-O-,-NR7-,-N=N-或-SO2-,R3和R4为氢,和R7是氢,甲基或乙基。
尤其优选的式(II)吡咯并吡咯是那些式中A和B为下式基团的式(II)吡咯并吡咯:式中R1和R2相互独立地为氢,甲基,叔丁基,氯,溴或CN。R2最好是氢,而A和B最好相同。
优选的式(III)喹吖啶酮是那些式中R8是氢、甲基或特别是氯的式(III)喹吖啶酮。
该新的固溶体可从上面定义的式(I)和(II)或(III)组分的物理混合物出发用下述本身已知的方法来制备:-使在极性有机溶剂中接触,最好是在回流温度一起搅拌组分的混合物,-使组分的混合物在极性有机溶剂中碱性再沉淀,或者将组分的混合物一起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,或者-酸性再沉淀,即将组分的混合物溶于酸中并通过用水稀释使固溶体沉淀,-充分研磨或捏合组分的混合物,随后在水和/或有机溶剂中重结晶或不进行重结晶这一步,其中具体实施可以例如按照美国专利第4783540号中详细描述的程序进行。
另一个新的制备方法包括使式(I)和(II)或(III)化合物按本身已知的方法与下列化合物按1∶2的摩尔比在非质子传递有机溶剂中在碱作为催化剂存在下反应:式(IV)二碳酸酯
D-O-D (IV),或者式(V)三卤代乙酸酯
(R9)3C-D (V),或者式(VI)叠氮化物
DN3 (VI),或者式(VII)碳酸酯
-CN取代的苯基,R11是-CN或-COOR10,和R12是未取代的或被卤素、C1-C4烷基、C1-C4烷氧基或-CN取代的苯
基,和R13、R14和R15相互独立地为氢,C1-C6烷基或C2-C5烯基,其中R13、
ⅰ)用通常已知的方法按1∶1的摩尔比以粉末形式均匀混合,或者
ⅱ)用通常已知的方法按1∶1的摩尔比以粉末形式均匀混合,随后将
该混合物溶于溶剂中,或者
ⅲ)首先将其全部溶解,然后以溶液形式以1∶1的比率混合,和然后-通过热处理、光解处理或化学处理使期望的混晶从该干燥的或溶解的混合物中沉淀。
R13、R14和R15,作为C2-C5烯基,是例如乙烯基,烯丙基,甲基烯丙基,正丁-2-烯基,2-甲基丙-2-烯基或正戊-2-烯基。
R13和R15最好是甲基,而R14最好是C1-C6烷基,特别是甲基。
优先选择使式(I)和(II)或(III)化合物与式(IV)二碳酸酯反应。
式(IV)二碳酸酯、式(V)三卤代乙酸酯、式(VI)叠氮化物、式(VII)碳酸酯和式(VIII)烷叉亚氨基氧基甲酸酯是已知的物质。若仍然是新的,则可以按与通常已知的方法相类似的方法来制备。
适宜的非质子传递有机溶剂的实例是醚类,例如四氢呋喃或二氧六环,或二醇醚类,例如乙二醇甲基醚、乙二醇乙基醚、二甘醇一甲基醚或二甘醇一乙基醚,还有偶极非质子传递溶剂,例如乙腈,苄腈,N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,硝基苯,N-甲基吡咯烷酮,卤代脂族或芳族烃类,例如三氯乙烷,苯或被烷基、烷氧基或卤素取代的苯,例如甲苯、二甲苯、茴香醚或氯苯,或芳族N-杂环,例如吡啶,甲基吡啶或喹啉。优选的溶剂的实例是四氢呋喃,N,N-二甲基甲酰胺和N-甲基吡咯烷酮。所述溶剂还可以以混合物的形式使用。每1重量份反应物宜使用5-20重量份溶剂。
适宜作为催化剂的碱的实例是碱金属本身,例如锂、钠或钾及它们的氢氧化物和碳酸盐,或者碱金属氨化物,例如氨基化锂、钠或钾,或者碱金属氢化物,例如氢化锂、钠或钾,或者碱土金属或碱金属的醇化物、特别是衍生自具有1至10个碳原子的脂肪族伯、仲或叔醇的醇化物,实例是甲醇锂、钠或钾,乙醇锂、钠或钾,正丙醇锂、钠或钾,异丙醇锂、钠或钾,正丁醇锂、钠或钾,仲丁醇锂、钠或钾,叔丁醇锂、钠或钾,2-甲基-2-丁醇锂、钠或钾,2-甲基-2-戊醇锂、钠或钾,3-甲基-3-戊醇锂、钠或钾,3-乙基-3-戊醇锂、钠或钾,还有有机脂族、芳族或杂环含氮碱,实例包括二氮杂二环辛烷,二氮杂二环十一碳烯和4-二甲氨基吡啶,和三烷基胺类,例如三甲胺或三乙胺。然而也可以使用这些碱的混合物。
优选有机含氮碱例如二氮杂二环辛烷,二氮杂二环十一碳烯,且特别是4-二甲氨基吡啶。
反应宜在大气压下在10-100℃之间、特别是18-40℃之间的温度、最好是在室温进行。
式(I)、(II)或(III)化合物或者用通常已知的方法按需要的比率以粉末形式混合并将该混合物溶于溶剂中,或者将它们先溶解,然后将溶液按需要的比率混合。
使用下列溶剂可能是适宜的:醚类,例如四氢呋喃或二氧六环,或二醇醚类,例如乙二醇甲基醚,乙二醇乙基醚,二甘醇一甲基醚或二甘醇一乙基醚,多元醇类,例如聚乙二醇,酮类,例如丙酮,乙基甲基酮,异丁基甲基酮或环己酮,还有偶极非质子传递溶剂,例如乙腈,苄腈,N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,硝基苯,N-甲基吡咯烷酮,二甲亚砜,卤代脂族或芳族烃类,例如三氯乙烷,二氯甲烷,氯仿,苯或被烷基、烷氧基或卤素取代的苯,例如甲苯、二甲苯、茴香醚或氯苯,芳族N-杂环,例如吡啶,甲基吡啶或喹啉。或高沸点溶剂,例如萘烷,正十二烷或煤油,或它们的混合物。优选的溶剂的实例是甲苯,二苯基醚,N-甲基吡咯烷酮,N,N-二甲基甲酰胺,二甲亚砜和喹啉。
式(I)、(II)和/或(III)化合物在溶剂或溶剂系统中的浓度根据所用的溶剂可能会变动很大。按总溶液计,宜使用0.1-20%(重量)、最好是0.2-5%(重量)的式(I)、(II)和/或(III)化合物。
通过处理干燥的或溶解的混合物可以非常简单地从该干燥的或溶解的混合物中获得由式(I)、(II)或(III)化合物构成的固溶体;所述处理或者是a)热处理,即例如在50-400℃、最好是100-200℃之间的温度加热或进行激光照射,或者是b)光解处理,即例如暴露至375nm以下波长的光中,或者是c)化学处理,即例如用有机或无机酸例如乙酸、甲苯磺酸、三氟乙酸、盐酸或硫酸处理,并用常规方法分离所生成的产物。
形成新的固溶体的组分之间的比率最好是60-90%(重量)的式(I)吡咯并吡咯对40-10%(重量)的式(II)吡咯并吡咯或者80-90%(重量)的式(I)吡咯并吡咯对20-10%(重量)的式(III)喹吖啶酮。
若需要对该新的固溶体进行重结晶或热处理,则按用于颜料的常规方法进行。一般来讲,这涉及在大气压或超计大气压下在水或有机溶剂中的热处理。最好使用有机溶剂例如被卤原子、烷基或硝基取代的苯,例如二甲苯,氯苯,邻二氯苯或硝基苯,和吡啶碱类,例如吡啶,甲基吡啶或喹啉,还有酮类,例如环己酮,醇类,例如异丙醇、丁醇或戊醇,醚类,例如乙二醇一甲基醚或一乙基醚,酰胺类,例如二甲基甲酰胺或N-甲基吡咯烷酮,和二甲亚砜或四氢噻吩砜。后处理还可以在水中在大气压或超计大气压下在有机溶剂存在和/或加入表面活性剂的条件下进行。
该新的固溶体可用作颜料用于将高分子有机材料着色。
可用该新固溶体着色的高分子有机材料的实例是纤维素醚或纤维素酯,例如乙基纤维素、硝基纤维素、乙酸纤维素、丁酸纤维素,天然树脂或合成树脂,例如加聚树脂或缩聚树脂,例如氨基树脂,尤其是脲/甲醛和三聚氰胺/甲醛树脂,醇酸树脂,酚醛树脂,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以混合物的形式作为塑料、熔体或以纺丝溶液、油漆、涂料或印刷油墨的形式存在。根据预定用途,使用该新固溶体作为有机颜料或者以制剂形式使用该新固溶体可能是有利的。
按待着色高分子有机材料计,该新固溶体可按0.01-30%(重量)、最好是0.1-10%(重量)的量来使用。
用该新固溶体将高分子有机物质着色通过将这样的固溶体,若需要,以母料形式,用辊压机或者混合或研磨设备掺入这些基料中来实施。然后将该已着色的材料用本身已知的方法例如压延、压塑、挤塑、涂布、铸塑或注塑方法制成期望的最终形式。为制备非刚性模制品或者降低它们的脆性,在成型步骤前将增塑剂掺入该高分子化合物中常常是合乎需要的。可使用的这样的增塑剂的实例是磷酸、苯二甲酸或癸二酸的酯。增塑剂可在将该新固溶体掺入之前或之后掺入所述聚合物中。为获得不同的色泽,除该新固溶体外,还可以将填充剂和/或其它能赋予颜色的成分例如白色颜料、有色颜料或黑色颜料以任何期望的量加至该高分子有机物质中。
为使油漆、涂料和印刷油墨着色,将所述高分子有机材料和新固溶体连同,若期望,添加剂例如填充剂、其它的颜料、干燥剂或增塑剂一起溶于或者细分散于普通的有机溶剂或溶剂混合物中。在这种情况下,可以将各组分单独或者将几种组分一起分散或溶解,然后将所有组分混合。
所述新的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、尤其是汽车用油漆着色。
当着色应用时,例如使聚氯乙烯或聚烯烃着色时,该新固溶体也显著具有良好的普通颜料性质例如良好的分散性,高色强度和纯洁度,良好的耐渗移、耐热、耐日光和耐气候牢度,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1a)
可溶性二酮吡咯并吡咯的制备
将14.75g(0.0512mol)3,6-二苯基-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮和27.94g(0.128mol)二碳酸二叔丁酯在500ml四氢呋喃中的混合物与3.23g(0.0264mol)4-二甲氨基吡啶混合。将如此获得的红色悬浮液在隔绝大气湿气的条件下于室温搅拌2小时。减压蒸除溶剂。将黄色的残留物用甲醇洗涤,并于室温真空干燥,得到23.8g(收率95%)N,N二叔丁氧基羰基-3,6-二苯基-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮。分析: C H N计算值: 68.84% 5.78% 5.73%实测值: 68.71% 5.79% 5.71%
实施例1b)
可溶性二酮吡咯并吡咯的制备
将11.01g(0.025mol)3,6-双(4-联苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮在500ml N,N-二甲基甲酰胺(经分子筛干燥)中的悬浮液与1.70g(0.014mol)4-二甲氨基吡啶混合,然后与13.64g(0.062mol)二碳酸二叔丁酯混合。将反应混合物在隔绝大气湿气的条件下于室温搅拌。20小时后,再加入13.64g(0.062mol)二碳酸二叔丁酯,并继续搅拌70小时。滤出沉淀物,用甲醇洗涤,并于室温真空干燥,得到14.0g(收率87%)橙色产物。分析: C H N计算值: 74.98% 5.66% 4.37%实测值: 74.22% 5.75% 4.92%
实施例1c
固溶体的制备
将0.98g(2.0mmol)得自a)的产物和5.13g(8.0mmol)得自b)的产物的混合物在200ml甲苯中在搅拌下加热至70℃。向所得到的混合物中加入20.0g(0.10mol)甲苯-4-磺酸一水合物,加热至110℃,并将该混合物在该温度搅拌2小时,然后放冷至室温。滤出形成的固体物质,用甲醇和水依次洗涤,并于80℃真空干燥,得到3.3g(收率80%)红色粉末。分析: C H N计算值:80.84% 4.52% 6.83%实测值:81.09% 4.31% 6.67%
全X射线衍射图采用常规方法用SIEMENS D500X射线衍射仪(CuKα照射)测定。
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,) (2Θ) (%)
22.6969 3.89 100
11.1340 7.93 16
7.3831 11.98 17
4.9988 17.73 75
4.7213 18.78 48
4.4016 20.16 16
3.6334 24.48 13
3.4269 25.98 23
3.3602 26.51 51
3.2202 27.68 28
3.1623 28.20 17
3.0660 29.10 14
提供主体晶格的化合物3,6-双(4-联苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮的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,) (2Θ) (%)
22.1785 3.98 51
11.0008 8.03 10
7.3287 12.07 12
4.9809 17.79 100
4.7273 18.76 59
4.3773 20.27 11
3.6218 24.56 14
3.4124 26.09 29
3.3473 26.61 85
3.2073 27.79 39
3.1654 28.17 17
3.0553 29.21 17
比较表明这两个X射线衍射图实质上是相同的。
实施例2
将0.80g(2.24mmol)3,6-双(4-氯苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮、2.24g(5.08mmol)3,6-双(4-联苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮和0.93g(16.58mmol)氢氧化钾在65ml二甲亚砜中的混合物在搅拌下加热至50℃,并在该温度下搅拌2小时。将所得到的紫色溶液倒入20℃的150ml水、60ml甲醇和0.91ml(16.63mmol)浓硫酸混合物中,然后将混合物于室温搅拌6小时。滤出沉淀的颜料,用甲醇和水依次洗涤,并于60℃真空干燥,得到2.64g(收率87%)红色粉末。分析: C H N Cl计算值: 76.31% 4.12% 6.74% 5.12%实测值: 74.79% 4.29% 6.57% 5.22%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,) (2Θ) (%)
22.1548 3.99 100
10.9616 8.06 16
7.3090 12.10 24
4.9515 17.90 75
4.7245 18.77 58
4.3778 20.27 25
3.6162 24.60 26
3.3633 26.48 54
3.3416 26.66 62
3.1908 27.94 41
3.1602 28.22 38
实施例3
按实施例2中所述操作,只是用2,9-二氯喹吖啶酮(1.54mmol)和3,6-双(4-联苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮(6.02mmol)代替相应的颜料,得到2.98g(收率92%)红色粉末。分析: C H N Cl计算值: 78.46% 4.23% 6.53% 3.31%实测值: 76.92% 4.31% 6.35% 3.32%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,) (2Θ) (%)
23.1808 3.81 100
11.0967 7.96 16
7.3487 12.03 24
5.0351 17.60 56
4.9901 17.76 62
4.7163 18.80 55
4.4141 20.10 27
3.3733 26.40 62
3.3579 26.52 63
3.2247 27.64 48
3.2065 27.80 43
实施例4
将1.43g(4mmol)3,6-双(4-氯苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮、2.64g(6mmol)3,6-双(4-联苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮和1.68g氢氧化钾在70ml二甲亚砜中的混合物加热至60℃,并在该温度下搅拌2.5小时。然后将反应混合物加至0.81ml浓硫酸和240ml水的溶液中并于60℃搅拌3小时。将该红色悬浮液过滤,并将残渣用甲醇和水依次洗涤,于60℃真空干燥,得到3.5g(收率84%)红色粉末。分析: C H N Cl计算值: 73.29% 3.88% 6.96% 7.94%实测值: 74.47% 4.07% 6.87% 6.93%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,) (2Θ) (%)
22.544 3.92 100
11.052 7.99 20
7.359 12.02 28
4.974 17.82 96
4.795 18.49 73
4.386 20.23 28
3.624 24.54 33
3.413 26.09 46
3.349 26.59 75
3.206 27.80 54
3.165 28.17 48
2.911 30.69 22
实施例5
将5.7g(16mmol)3,6-双(4-氯苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮、10.6g(24mmol)3,6-双(4-联苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮和6.73g氢氧化钾在250ml叔戊醇中的混合物加热至100℃,并在该温度下搅拌1小时。然后将反应混合物冷却至60℃,加至冷却至0℃的170ml甲醇和170ml水的溶液中,接着于0℃搅拌2小时。将该红色悬浮液过滤,并将残渣用甲醇和水依次洗涤,于80℃真空干燥,得到14.8g(收率90.8%)红色粉末。分析: C H N Cl计算值: 73.29% 3.88% 6.96% 7.94%实测值: 73.48% 3.89% 6.70% 7.21%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,) (2Θ) (%)
22.365 3.95 100
11.041 8.00 21
7.404 11.94 30
4.912 18.05 63
4.734 18.73 55
4.436 20.00 29
3.617 24.59 28
3.462 25.71 30
3.339 26.68 46
3.165 28.17 39
实施例6
将2.14g(6mmol)3,6-双(4-氯苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮、10.57g(24mmol)3,6-双(4-联苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮和5.05g氢氧化钾在200ml叔戊醇中的混合物加热至100℃,并在该温度下搅拌1小时。然后将反应混合物冷却至80℃,加至冷却至0℃的2.64ml浓硫酸、300ml甲醇和300ml水的溶液中,接着于0℃搅拌2小时。将该红色悬浮液过滤,并将残渣用甲醇和水依次洗涤,于80℃真空干燥,得到11.85g(收率93%)红色粉末。分析: C H N Cl计算值: 77.55% 4.22% 6.66% 3.97%实测值: 77.52% 4.41% 6.44% 3.44%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,) (2Θ) (%)
23.785 3.71 100
11.421 7.74 13
7.573 11.68 21
4.968 17.84 54
4.774 18.57 45
4.704 18.85 38
4.505 19.69 22
3.647 24.39 16
3.449 25.81 26
3.354 26.55 41
3.185 27.99 23
实施例7
按实施例6中所述操作,但用2,9-二氯喹吖啶酮(6mmol)和3,6-双(4-联苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮(24mmol)代替相应的颜料,得到12.6g(收率98%)红色粉末。分析: C H N Cl计算值: 78.04% 4.19% 6.56% 3.72%实测值: 76.32% 4.13% 6.24% 3.40%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,) (2Θ) (%)
23.522 3.75 100
11.344 7.79 18
7.555 11.70 28
4.954 17.89 66
4.724 18.77 50
4.523 19.61 29
3.350 26.59 50
3.249 27.43 50
3.023 29.52 24
实施例8
将0.76g(2mmol)2,9-二氯喹吖啶酮、3.52g(8mmol)3,6-双(4-联苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮和120ml DowthermA(=联苯/二苯基醚混合物)的混合物加热至250℃,并在该温度下搅拌4小时。然后将反应混合物冷却至80℃,将该红色悬浮液过滤,并将残渣用甲醇和水依次洗涤,于80℃真空干燥,得到3.85g(收率90%)红色粉末。分析: C H N Cl计算值: 78.04% 4.19% 6.56% 3.72%实测值: 77.68% 4.07% 6.40% 3.42%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,) (2Θ) (%)
22.078 3.99 100
10.990 8.04 19
7.309 12.10 21
4.980 17.80 64
4.736 18.72 37
4.373 20.29 18
3.622 24.56 13
3.413 26.08 17
3.349 26.60 50
3.211 27.77 44
3.035 29.41 12
实施例9
将1.09g(3mmol)3-苯基-6-(4-联苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮、2.64g(6mmol)3,6-双(4-联苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮和1.51g氢氧化钾在60ml二甲亚砜中的混合物加热至50℃,并在该温度下搅拌4.5小时。然后将反应混合物加至60ml甲醇和240ml水的溶液中,并于室温搅拌4小时。将该红色悬浮液过滤,并将残渣用甲醇和水依次洗涤,于60℃真空干燥,得到3.4g(收率91%)红色粉末。分析: C H N计算值: 80.90% 4.53% 6.80%实测值: 79.52% 4.60% 6.47%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,) (2Θ) (%)
23.595 3.74 100
11.513 7.67 13
7.450 11.87 20
5.015 17.67 49
4.759 18.63 51
4.505 19.69 29
3.638 24.45 17
3.347 26.61 57
3.221 27.67 29
3.055 29.21 15
实施例10
将0.42g(1.46mmol)3,6-二苯基-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮、2.58g(5.86mmol)3,6-双(4-联苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮和0.91g氢氧化钾在90ml二甲亚砜中的混合物加热至50℃,并在该温度下搅拌2小时。然后将反应混合物加至0.88ml浓硫酸、90ml甲醇和180ml水的溶液中,并于60℃搅拌3小时。将该红色悬浮液过滤,并将残渣用甲醇和水依次洗涤,于60℃真空干燥,得到2.5g(收率82%)红色粉末。分析: C H N计算值: 80.84% 4.52% 6.86%实测值: 79.95% 4.72% 6.71%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,) (2Θ) (%)
23.385 3.77 100
11.069 7.98 15
7.410 11.93 24
4.905 18.07 65
4.769 18.59 60
3.719 23.91 19
3.354 26.55 61
3.163 28.19 30
实施例11
重复实施例9中所述的操作,但用2,9-二甲基喹吖啶酮(2mmol)和3,6-双(4-联苯基)-2,5-二氢吡咯并[3,4-c]吡咯-1,4-二酮(8mmol)代替相应的颜料,得到3.8g(收率91%)红色粉末。分析: C H N计算值: 80.97% 4.61% 6.74%实测值: 79.50% 4.75% 6.35%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,) (2Θ) (%)
23.202 3.80 100
11.115 7.95 15
7.475 11.83 28
4.993 17.75 59
4.734 18.73 59
3.673 24.21 23
3.347 26.62 67
3.154 28.27 30
3.049 29.27 24
实施例12
按类似于实施例8中所述操作,但用0.68g 2,9-二甲基喹吖啶酮代替0.76g 2,9-二氯喹吖啶酮,得到3.9g(收率93%)红色粉末。分析: C H N计算值: 80.97% 4.61% 6.74%实测值: 80.60% 4.50% 6.39%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,) (2Θ) (%)
22.392 3.94 100
11.064 7.98 18
7.344 12.04 20
4.993 17.75 71
4.758 18.63 42
4.387 20.22 17
3.629 24.51 14
3.418 26.05 20
3.355 26.55 51
3.215 27.72 27
3.165 28.17 16
3.048 29.28 15
实施例13
按类似于实施例8中所述操作,只是用0.62g喹吖啶酮代替实施例8中所用的0.76g 2,9-二氯喹吖啶酮,得到3.8g(收率92%)红色粉末。分析: C H N计算值: 80.82% 4.43% 6.88%实测值: 80.82% 4.34% 6.53%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 ) (2Θ) (%)
22.208 3.98 100
11.005 8.03 17
4.985 17.78 56
4.739 18.71 33
4.378 20.27 15
3.624 24.54 10
3.410 26.11 17
3.350 26.59 44
3.211 27.76 23
3.161 28.21 12
3.053 29.23 11
实施例14
将7.5g实施例1的固溶体、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)用振摇机一起分散90分钟(总涂料量150g;5%的颜料);所述CAB溶液由41.0g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、18.5gSOLVESSO150(芳烃;ESSO)、21.5g乙酸丁酯和17.5g二甲苯组成。
将27.69g所形成的主色漆(masstonelacquer)与17.31g Al储液(8%)混合作为底涂层配剂,并将其通过喷雾涂布至铝板上(湿膜大约20μm);所述Al储液由12.65 gSILBERLINE SS 3334AR(60%)(Silberline Ltd.)、56.33g CAB溶液(组成见上)、20.81g聚酯树脂DYNAPOL H700、2.60g三聚氰胺树脂MAPRENAL MF650和7.59gSOLVESSO150组成。于室温蒸发30分钟后,将热固性丙烯酸类漆作为罩面漆喷至其上(湿膜大约50μm);所述热固性丙烯酸类漆由29.60g丙烯酸类树脂URACRON2263 XB,(50%,在二甲苯/丁醇中)(Chem.Fabrik Schweizerhalle)、5.80g三聚氰胺树脂CYMEL327(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有机硅液(1%,在二甲苯中)、3.00g抗光剂TINUVIN900(10%,在二甲苯中)(Ciba)和1.00g抗光剂TINUVIN292(10%,在二甲苯中)(Ciba)组成。然后将涂层在室温再蒸发30分钟后,将其于130℃烘30分钟。得到具有非常好的耐力性能的红色涂层。
实施例15
将0.6g得自实施例2的固溶体与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摇床(roller table)上于160℃处理15分钟使成薄膜。如此制得的红色PVC膜具有很高的色强度并对渗移和光稳定。
实施例16
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℃的温度抽丝,得到具有极佳的耐光牢度和织物牢度性能的红色纤维。
Claims (10)
1.由式(I)吡咯并吡咯和a)式(II)吡咯并吡咯或b)式(III)喹吖啶酮以(I)∶(II)或(I)∶(III)为20-90%(重量)∶80-10%(重量)的相应比率构成的固溶体;所述式(I)如下:所述式(II)如下: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,C1-C18烷氧基羰基,C1-C18烷基氨基羰基,-CN,-NO2,三氟甲基,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;式中R8为氢,卤素,C1-C6烷基或C1-C6烷氧基。
3.按照权利要求2的固溶体,它包含式中A和B为下式基团的式(II)吡咯并吡咯:式中R1和R2相互独立地为氢,甲基,叔丁基,氯,溴或CN。
4.按照权利要求1的固溶体,它包含式中R8是氢、甲基或氯的式(III)喹吖啶酮。
5.按照权利要求1的固溶体,由式(I)吡咯并吡咯和式(II)吡咯并吡咯按(I)∶(II)为60-90%(重量)∶40-10%(重量)的比率组成。
6.按照权利要求1的固溶体,由式(I)吡咯并吡咯和式(III)喹吖啶酮按(I)∶(III)为80-90%(重量)∶20-10%(重量)的比率组成。
7.按照权利要求1的固溶体的制备方法,它包括使式(I)和(II)或(III)化合物按本身已知的方法与下列化合物按1∶2的摩尔比在非质子传递有机溶剂中在碱作为催化剂存在下反应:式(IV)二碳酸酯
D-O-D (IV),或者式(V)三卤代乙酸酯
(R9)3C-D (V),或者式(VI)叠氮化物
DN3 (VI),或者式(VII)碳酸酯
D-OR10 (VII),或者式(VIII)烷叉亚氨基氧基甲酸酯式中D是下式基团: 或
R9是氯、氟或溴,R10是C1-C4烷基或未取代的或被卤素、C1-C4烷基、C1-C4烷氧基或CN取代的苯基,R11是-CN或-COOR10,和R12是未取代的或被卤素、C1-C4烷基、C1-C4烷氧基或CN取代的苯基,和R13、R14和R15相互独立地为氢,C1-C6烷基或C2-C5烯基,其中R13、R14和R15中的至少两个必须是烷基或烯基,得到可溶性下式化合物:或式中A、B和R8具有权利要求1中的定义,-将式(IX)和(X)化合物或式(IX)和(XI)化合物或者
ⅰ)用通常已知的方法按1∶1的摩尔比以粉末形式均匀混合,或
者
ⅱ)用通常已知的方法按1∶1的摩尔比以粉末形式均匀混合,随
后将该混合物溶于溶剂中,或者
ⅲ)首先将其全部溶解,然后以溶液形式以1∶1的比率混合,和然后-通过热处理、光解处理或化学处理使期望的混晶从该干燥的或溶解的混合物中沉淀。
8.按照权利要求1的固溶体作为染料在用于使高分子有机材料着色方面的用途。
9.按照权利要求8用途,其中所述高分子有机材料是塑料。
10.按照权利要求8的用途,其中所述高分子有机材料是表面涂料。
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EP0877058B1 (de) * | 1997-05-06 | 2002-07-03 | Ciba SC Holding AG | Diketopyrrolopyrrolzusammensetzungen |
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GB9823803D0 (en) | 1998-10-31 | 1998-12-23 | Ciba Geigy Ag | Novel solid solutions of monoazo pigments |
DE19958181A1 (de) | 1999-12-02 | 2001-06-07 | Clariant Gmbh | Pigmentdispergatoren auf Basis von Diketopyrrolopyrrolverbindungen und Pigmentzubereitungen |
AU2001270600A1 (en) | 2000-07-07 | 2002-01-21 | Ciba Specialty Chemicals Holding Inc. | Pigmentary copper phthalocyanine solid solution and transparent dispersion comprising it |
CA2443708A1 (en) | 2001-04-24 | 2002-10-31 | Ciba Specialty Chemicals Holding Inc. | Pigment compositions and pigmented water-based coating materials |
SI1403271T1 (sl) * | 2002-09-25 | 2006-04-30 | Degussa | Postopek za pripravo 5-formil-2-furilborove kisline |
RU2329281C2 (ru) * | 2002-10-07 | 2008-07-20 | Циба Спешиалти Кемикэлз Холдинг Инк. | Непрозрачное пигментированное красителем покрытие |
DE102004039954A1 (de) * | 2004-08-18 | 2006-02-23 | Clariant Gmbh | Verfahren zum verzugsfreien Pigmentieren von teilkristallinen Kunststoffen |
DE102007049883A1 (de) * | 2007-10-18 | 2009-04-23 | Clariant International Ltd. | Diketopyrrolopyrrol-Mischkristalle |
KR101939419B1 (ko) | 2010-12-30 | 2019-01-16 | 바스프 에스이 | 표면-개질된 안료 제제 |
JP6179075B2 (ja) * | 2011-09-02 | 2017-08-16 | 大日本印刷株式会社 | カラーフィルタ用赤色顔料分散液及びその製造方法、カラーフィルタ用赤色感光性樹脂組成物及びその製造方法、カラーフィルタ、並びに、液晶表示装置及び有機発光表示装置 |
US10037991B2 (en) | 2014-01-09 | 2018-07-31 | Taiwan Semiconductor Manufacturing Company Limited | Systems and methods for fabricating FinFETs with different threshold voltages |
JP2019112534A (ja) * | 2017-12-25 | 2019-07-11 | 東洋インキScホールディングス株式会社 | ジケトピロロピロール顔料固溶体組成物、ならびに該ジケトピロロピロール顔料固溶体組成物を用いた着色組成物 |
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EP0654506A2 (de) * | 1993-11-22 | 1995-05-24 | Ciba-Geigy Ag | Verfahren zur Herstellung synergistischer Pigmentgemische |
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ATE22104T1 (de) * | 1982-05-17 | 1986-09-15 | Ciba Geigy Ag | Herstellung von pyrrolo-(3,4-c)-pyrrolen. |
DE3584138D1 (de) * | 1984-11-07 | 1991-10-24 | Ciba Geigy Ag | Pigmentmischungen. |
US4783540A (en) * | 1986-08-07 | 1988-11-08 | Ciba-Geigy Corporation | Solid solutions of pyrrolo-(3,4-C)-pyrrols |
US4810304A (en) * | 1987-02-02 | 1989-03-07 | Ciba-Geigy Corporation | Solid solutions of pyrrolo-(3,4-C)-pyrroles with quinacridones |
TW372244B (en) * | 1993-07-29 | 1999-10-21 | Ciba Sc Holding Ag | Process for producing novel finely divided highly transparent diketopyrrolopyrrole pigments |
US5584922A (en) * | 1994-09-14 | 1996-12-17 | Ciba-Geigy Corporation | Stir-in organic pigments |
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 |
US5641351A (en) * | 1995-04-14 | 1997-06-24 | Ciba-Geigy Corporation | Pigment compositions based on 3,6-di(biphenyl)1,4-diketo-pyrrolo[3,4c]-pyrrole |
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1996
- 1996-08-27 TW TW085110404A patent/TW370546B/zh active
- 1996-09-10 DE DE59609043T patent/DE59609043D1/de not_active Expired - Lifetime
- 1996-09-10 EP EP96810600A patent/EP0763572B1/de not_active Expired - Lifetime
- 1996-09-12 US US08/712,722 patent/US5821373A/en not_active Expired - Lifetime
- 1996-09-16 CA CA002185618A patent/CA2185618A1/en not_active Abandoned
- 1996-09-17 KR KR1019960040415A patent/KR100452658B1/ko not_active IP Right Cessation
- 1996-09-17 CN CN96122501A patent/CN1076369C/zh not_active Expired - Fee Related
- 1996-09-18 JP JP24580296A patent/JP4335322B2/ja not_active Expired - Fee Related
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EP0654506A2 (de) * | 1993-11-22 | 1995-05-24 | Ciba-Geigy Ag | Verfahren zur Herstellung synergistischer Pigmentgemische |
Also Published As
Publication number | Publication date |
---|---|
CN1158873A (zh) | 1997-09-10 |
KR970015646A (ko) | 1997-04-28 |
EP0763572A3 (de) | 1998-04-01 |
CA2185618A1 (en) | 1997-03-19 |
US5821373A (en) | 1998-10-13 |
TW370546B (en) | 1999-09-21 |
KR100452658B1 (ko) | 2005-01-15 |
EP0763572A2 (de) | 1997-03-19 |
JP4335322B2 (ja) | 2009-09-30 |
JPH09132575A (ja) | 1997-05-20 |
DE59609043D1 (de) | 2002-05-16 |
EP0763572B1 (de) | 2002-04-10 |
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