JPH04154780A - Tetrahydroxyquinacridine derivative and its production - Google Patents
Tetrahydroxyquinacridine derivative and its productionInfo
- Publication number
- JPH04154780A JPH04154780A JP2275286A JP27528690A JPH04154780A JP H04154780 A JPH04154780 A JP H04154780A JP 2275286 A JP2275286 A JP 2275286A JP 27528690 A JP27528690 A JP 27528690A JP H04154780 A JPH04154780 A JP H04154780A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- general formula
- formula
- quinacridone
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 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 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 18
- 150000001875 compounds Chemical class 0.000 abstract description 18
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract description 10
- 239000000463 material Substances 0.000 abstract description 6
- 239000000976 ink Substances 0.000 abstract description 4
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 abstract description 3
- 239000012024 dehydrating agents Substances 0.000 abstract description 3
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 abstract description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003086 colorant Substances 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000049 pigment Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- -1 propokine group Chemical group 0.000 description 7
- 235000019646 color tone Nutrition 0.000 description 6
- 238000004040 coloring Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000007416 differential thermogravimetric analysis Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SCZWJXTUYYSKGF-UHFFFAOYSA-N 5,12-dimethylquinolino[2,3-b]acridine-7,14-dione Chemical compound CN1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3N(C)C1=C2 SCZWJXTUYYSKGF-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 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
- 125000006611 nonyloxy group Chemical group 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 125000005447 octyloxy group Chemical group [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])O* 0.000 description 1
- 150000007524 organic acids Chemical class 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
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000001054 red pigment Substances 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
- 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
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、自動車用塗料、印刷インキ、プラスチック材
料用の着色材として有用な新規テトラヒトロキナクリジ
ン誘導体およびその製造法を提供するものである。[Detailed Description of the Invention] [Industrial Application Field] The present invention provides a novel tetrahydroquinacridine derivative useful as a colorant for automobile paints, printing inks, and plastic materials, and a method for producing the same. .
一般に、塗料、印刷インキ、樹脂の着色などに用いられ
る色材は、顔料か主であり、無機系と有機系に大別され
る。有機顔料は、無機系と比較して彩度、透明度、着色
力に優れ、種類も豊富な為、広（多用されている。着色
材としての用途に要求される特性として、１）色調か鮮
明であること、２）耐光性、３）耐熱性、４）耐薬品性
、５）耐溶剤性、６）分散性および７）耐摩擦堅牢性か
優れていることなどが挙げられる。特に、耐光性の強い
顔料を得るために、これらの有機顔料の特性を改良する
検討か行われ、例えば、アゾ顔料のもつ欠点、すなわち
、耐マイグレーション性、耐候性、耐熱性を改良し、銅
フタロシアニン顔料の性能に近づける試みか行われてい
るか、特に良好な結果は得られていない（特公昭５５−
１０６３０、特公昭５５−４９０８７、特開昭５５−１
３５１６５、特開昭６ｉ８３２５７参照）。又、従来の
キナクリドン顔料の性能を改良する検討か行われ、例え
ば、新しいキナクリドン顔料として、アサキナクリドン
顔料（Ｂｕｌｌ、Ｃｈｅｍ、Ｓｏｃ、Ｊｐｎ、 、４８
５９１（１９７５）、日化；志、 ３９８（１９７９）
、 Ｈｅ１ｖ、 Ｃｈｉｍ、 Ａｃｔａ、 ６１１１４
６（＋９７８）参照）等か報告されているが、それらは
、これらの要求を必ずしも満足していない。In general, coloring materials used for coloring paints, printing inks, resins, etc. are mainly pigments, and are broadly classified into inorganic and organic types. Organic pigments have superior chroma, transparency, and coloring power compared to inorganic pigments, and are available in a wide variety of types, so they are widely used.Characteristics required for use as coloring materials include: 1) color tone and clarity; 2) light resistance, 3) heat resistance, 4) chemical resistance, 5) solvent resistance, 6) dispersibility, and 7) excellent abrasion fastness. In particular, in order to obtain pigments with strong light resistance, studies have been conducted to improve the properties of these organic pigments. For example, by improving the migration resistance, weather resistance, and heat resistance of azo pigments, Attempts have been made to approach the performance of phthalocyanine pigments, but no particularly good results have been obtained (Japanese Patent Publication No. 1973-
10630, JP 55-49087, JP 55-1
35165, see Japanese Patent Application Laid-open No. 6i83257). In addition, studies have been conducted to improve the performance of conventional quinacridone pigments, and for example, asaquinacridone pigment (Bull, Chem, Soc, Jpn, 48
591 (1975), Nikka; Shi, 398 (1979)
, He1v, Chim, Acta, 61114
6 (+978)), but they do not necessarily satisfy these requirements.
本発明者らは、このような状況に鑑み、従来技術の問題
点を解決すべく使用適性の優れた着色材について鋭意研
究を重ねた結果、有用で新規なテトラヒドロキナクリジ
ン誘導体およびその製造法を見出し、本発明を完成する
に到った。In view of this situation, the present inventors have conducted intensive research on coloring materials with excellent usability in order to solve the problems of the conventional technology, and as a result, have discovered a useful and novel tetrahydroquinacridine derivative and a method for producing the same. This finding led to the completion of the present invention.
即ち、本発明は、
■）一般式［１１
（式中、Ｒ１１Ｒ２およびＲ２は水素原子、ハロゲン原
子、アルキル基、アルコキシ基を表わし、Ｒ，、Ｒ。That is, the present invention has the following characteristics: (1) General formula [11 (wherein, R11R2 and R2 represent a hydrogen atom, a halogen atom, an alkyl group, or an alkoxy group;
およびＲ２は同一でも異なってもよい。Ｒ４，Ｒ，はそ
れぞれ水素原子、アルキル基、アルケニル基、アラルキ
ル基およびアリール基を表わし、Ｒ４およびＲ５は同一
でも異なってもよい。）
て表わされるテトラヒドロキナクリジン誘導体およびそ
の製造法をその要旨とするものである。and R2 may be the same or different. R4 and R each represent a hydrogen atom, an alkyl group, an alkenyl group, an aralkyl group, and an aryl group, and R4 and R5 may be the same or different. ) The gist of this paper is a tetrahydroquinacridine derivative represented by the following formula and a method for producing the same.
本発明で得られる前記一般式［１］で示されるテトラヒ
ドロキナクリジン誘導体は、新規化合物であり、このも
のは、一般式［２１
（式中、Ｒ１，Ｒ２およびＲ２は水素原子、ハロゲン原
子、アルキル基、アルコキシ基を表わし、Ｒ１，Ｒ２お
よびＲ３は同一でも異なってもよい。Ｒ４，Ｒｓはそれ
ぞれ水素原子、アルキル基、アルケニル基、アラルキル
基およびアリール基を表わし、Ｒ４およびＲ１は同一で
も異なってもよい。）
で表わされるキナクリドン誘導体をマロニトリルと反応
させることによって合成てきる。The tetrahydroquinacridine derivative represented by the general formula [1] obtained in the present invention is a new compound, and this derivative has the general formula [21 (wherein R1, R2 and R2 are hydrogen atoms, halogen atoms, alkyl R1, R2 and R3 may be the same or different. R4 and Rs each represent a hydrogen atom, an alkyl group, an alkenyl group, an aralkyl group and an aryl group, and R4 and R1 may be the same or different. ) can be synthesized by reacting a quinacridone derivative represented by the following with malonitrile.
本発明の態様を更に詳しく説明すると、テトラヒドロキ
ナクリジン誘導体を得る基本の反応は（式１）によって
表わされる。To explain the embodiment of the present invention in more detail, the basic reaction for obtaining a tetrahydroquinacridine derivative is represented by (Formula 1).
［２１
＋ ２Ｃｔ（ｚ（ＣＮ’ｂ −〉
［１１
（式中、Ｒ１＋ Ｒ２およびＲ２は水素原子、ハロゲン
原子、アルキル基、アルコキシ基を表わし、Ｒ，、Ｒ２
およびＲ３は同一でも異なってもよい。Ｒ，、Ｒ，はそ
れぞれ水素原子、アルキル基、アルケニル基、アラルキ
ル基およびアリール基を表わし、Ｒ４およびＲ６は同一
でも異なってもよい。）
すなわち、公知の方法で得られる一般式［２１て表わさ
れるキナクリドン誘導体（Ｕ、 Ｓ、 Ｓ、 Ｒ４５５
，＋０２゜王化誌、７０．２１９９（１９６７）参照）
とマロノニトリルを有機溶媒中、又は、無溶媒中で、脱
水剤の存在下、所定の温度で、所定の時間反応させ対応
する一般式［１］て示されるトテラヒドロキナクリジン
誘導体を高品質で合成することか出来る。[21 + 2Ct(z(CN'b ->
and R3 may be the same or different. R and R each represent a hydrogen atom, an alkyl group, an alkenyl group, an aralkyl group, and an aryl group, and R4 and R6 may be the same or different. ) That is, a quinacridone derivative represented by the general formula [21 (U, S, S, R455
)
and malononitrile in an organic solvent or in the absence of a solvent, in the presence of a dehydrating agent, at a predetermined temperature, for a predetermined period of time to synthesize a high-quality toterahydroquinacridine derivative represented by the corresponding general formula [1]. I can do something.
前記、一般式［１１，一般式［２］および（式ｌ）て示
されるＲ、、 Ｒ２，Ｒ２，Ｒ４，Ｒａのうち、アルキ
ル基としては、例えばメチル基、エチル基、プロピル基
、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オ
クチル基、ノニル基、デシル基、ラウリル基、ヘキサデ
シル基、ステアリル基などが挙げられ、アルコキシ基と
しては、例えば、メトキシ基、エトキシ基、プロポキン
基、イソプロポキシ基、ブトキシ基、イソブトキシ基、
ｔｅｒｔ−ブトキシ基、ペンチルオキシ基、ヘキシル
オキシ基、ヘプチルオキシ基、オクチルオキシ基、ノニ
ルオキシ基、デシルオキシ基、ラウリルオキシ基、へキ
サデシルオキシ基、ステアリルオキシ基などが挙げられ
る。アルケニル基としては、例えは、アリル基、ブテニ
ル基、ペンテニル基、ヘキセニル基などが挙げられ、ア
ラルキル基としては、例えば、ベンジル基、ペンセン環
にクロル、メトキン基、または、ニトロ基か置換された
ベンジル基、フェネチル基などが挙げられ、アリール基
としては、フェニル基または置換されたフェニル基など
が挙げられる。ハロゲン原子としては、例えば、フッ素
、塩素、臭素などが挙げられる。Among R, R2, R2, R4, and Ra represented by the general formula [11, general formula [2] and (formula l), examples of the alkyl group include a methyl group, an ethyl group, a propyl group, and a butyl group. , pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, lauryl group, hexadecyl group, stearyl group, etc. Examples of the alkoxy group include methoxy group, ethoxy group, propokine group, isopropoxy group, etc. group, butoxy group, isobutoxy group,
Examples include tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, lauryloxy group, hexadecyloxy group, and stearyloxy group. Examples of the alkenyl group include an allyl group, a butenyl group, a pentenyl group, and a hexenyl group. Examples of the aralkyl group include a benzyl group and a pentene ring substituted with a chloro, metquine, or nitro group. Examples of the aryl group include a benzyl group and a phenethyl group, and examples of the aryl group include a phenyl group and a substituted phenyl group. Examples of the halogen atom include fluorine, chlorine, and bromine.
本発明て用いられる脱水剤は、Ｎ−メチルピロリジン、
Ｎ−メチルモルホリン、トリエチルアミン、ピペリジン
なとの塩基や、無水酢酸なとの酸無水物、又は、塩化亜
鉛、塩化アルミニウム、四塩化チタン、塩化第二スズ、
五酸化リン、五フッ化アンチモン、三フッ化ホウ素なと
のルイス酸、Ｐ−トルエンスルホン酸、ポリリン酸、硫
酸、塩化水素、リン酸なとの酸か挙げられるか、特に無
水酢酸のような有機酸無水物か好ましい。The dehydrating agent used in the present invention is N-methylpyrrolidine,
Bases such as N-methylmorpholine, triethylamine, piperidine, acid anhydrides such as acetic anhydride, or zinc chloride, aluminum chloride, titanium tetrachloride, tin chloride,
Lewis acids such as phosphorus pentoxide, antimony pentafluoride, and boron trifluoride, acids such as P-toluenesulfonic acid, polyphosphoric acid, sulfuric acid, hydrogen chloride, and phosphoric acid, especially acetic anhydride. Organic acid anhydrides are preferred.
本発明で用いられる溶媒は、原料であるマロノニトリル
およびキナクリドン誘導体を溶解し、反応させることか
てきるものであれば良く、例えば、ニトロベンゼン、ジ
クロロベンセン、キノリン、Ｎ、Ｎ−ジメチルホルムア
ミド、ジメチルスルホキシド、Ｎ−メチルピロリドン、
】、３−ジメチル−２−イミダゾリジノンの如き非プロ
トン性極性溶媒などが好ましい。The solvent used in the present invention may be any solvent as long as it can dissolve and react malononitrile and quinacridone derivatives as raw materials, such as nitrobenzene, dichlorobenzene, quinoline, N,N-dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone,
], aprotic polar solvents such as 3-dimethyl-2-imidazolidinone, etc. are preferred.
本発明において適用される反応温度は、テトラヒドロキ
ナクリジン誘導体の生成率か最も良好になるように適宜
選択か可能であり、４０〜２００℃、特に７０〜１５０
″Ｃか好ましい。The reaction temperature applied in the present invention can be appropriately selected so as to obtain the best production rate of the tetrahydroquinacridine derivative, and is 40 to 200°C, particularly 70 to 150°C.
``C is preferable.
従来のキナクリドン顔料として、例えば、無置換キナク
リドン（比較化合物［１１）又は、Ｎ、Ｎ〜ジメチルキ
ナクリドン（比較化合物［２１）か、赤色の色調を示す
のに対し、本発明に係わる前記一般式［１１で示される
新規なテトラヒドロキナクリジン誘導体は、青色の色調
を有するのが特徴であり、従来のキナクリドン顔料とは
全く異なった色調を持つことから、更に、広域の色調要
求に応えることができる。又、顔料としての基礎物性を
検討した結果、前記一般式［１］で示される新規なトテ
ラヒドロキナクリジン誘導体は、従来のキナクリドン顔
料（例えば、比較化合物［１］および［２１）と比較し
て、特に耐光性および耐熱性に優れているのか特徴であ
り、又、他の顔料諸物性として、例えば、耐薬品性、耐
溶剤性、分散性、耐摩擦堅牢性も良好であることから、
広範囲の用途が期待てきる。Conventional quinacridone pigments, for example, unsubstituted quinacridone (comparative compound [11) or N,N-dimethylquinacridone (comparative compound [21)], exhibit a red color tone, whereas those of the general formula [21] according to the present invention exhibit a red color tone. The novel tetrahydroquinacridine derivative represented by No. 11 is characterized by having a blue tone, which is completely different from that of conventional quinacridone pigments, and therefore can meet the needs of a wide range of color tones. In addition, as a result of examining the basic physical properties as a pigment, the novel toterahydroquinacridine derivative represented by the general formula [1] has superior properties compared to conventional quinacridone pigments (e.g., comparative compounds [1] and [21)]. In particular, it is characterized by its excellent light resistance and heat resistance, and other pigment physical properties such as chemical resistance, solvent resistance, dispersibility, and abrasion fastness are also good.
It is expected to have a wide range of applications.
本発明に係わる前記一般式［１１て示される新規なテト
ラヒドロキナクリシン誘導体は、従来のキナクリドン顔
料か、赤色の色調を示すのに対し、吸収極大か、１１６
〜１３０ｎｍ深色シフトするため、青色の色調を有する
のか特徴であり、従来のキナクリドン顔料とは全（異な
る色調を持つことから、更に、広域の色調要求に応える
ことかできる。又、顔料としての基礎物性を検討した結
果、前記−服代［１］で示される新規なテトラヒドロキ
ナクリジン誘導体は、従来のキナクリドン顔料（例えば
、比較化合物［１］および［２１）と比較して、特に耐
光性および耐熱性に優れていることが特徴であり、広範
囲の用途か期待てきる。The novel tetrahydroquinacrysin derivative represented by the general formula [11] according to the present invention exhibits a red color tone compared to conventional quinacridone pigments, whereas the absorption maximum is 116
Because it has a bathochromic shift of ~130 nm, it has a blue tone, and since it has a different tone from conventional quinacridone pigments, it can meet the needs of a wide range of color tones. As a result of examining the basic physical properties, the novel tetrahydroquinacridine derivative represented by the above-mentioned -Fukudai [1] has particularly good light resistance and It is characterized by excellent heat resistance, and is expected to be used in a wide range of applications.
以下、本発明を実施例により詳細に説明する。Hereinafter, the present invention will be explained in detail with reference to Examples.
〔合成例１〕
５、７．１２．１４−テトラヒトローフ、１４−ジシア
ノメチレン−キノ［２，３−ｂ］アク１ナジン（化合物
Ｎα１）の合成
５、１２．−ジヒドロ−キノ［２，３−ｂ］アクリジン
−７゜１４−ジオン０．５ｇ、マロンニトリルｌ、９４
ｇをプロピオン酸無水物２００７７１１に添加し、 １
６０〜１６５°Ｃて８時間攪拌した。反応終了後、室温
まで冷却し、析出した結晶をメタノールで洗浄し、青色
結晶性粉末として融点３００°Ｃ以上の化合物０．２９
ｇ （収率４５％）を得た。[Synthesis Example 1] 5,7.12.Synthesis of 14-tetrahytoloaf, 14-dicyanomethylene-quino[2,3-b]ac1 nadine (compound Nα1) 5,12. -dihydro-quino[2,3-b]acridine-7゜14-dione 0.5g, malonitrile l, 94
g to propionic anhydride 2007711, 1
The mixture was stirred at 60-165°C for 8 hours. After the reaction is completed, the precipitated crystals are cooled to room temperature and washed with methanol to form a blue crystalline powder with a melting point of 300°C or higher.
g (45% yield) was obtained.
〔合成例２〕
５、７．１２．１４−テトラヒドロ−５，１２−ジメチ
ル−７，１４−ジンアノメチレン−キノ［２，３−ｂ］
アクリジン（化合物漸２）の合成
５．１２．−ジヒドロ−５，１２−ジメチル−キノ［２
，３−ｂｌアクリジン−７，１４−ジオン１．６ｇ、マ
ロノニトリル６．２ｇを無水酢酸５００ｍｊ’に添加し
、１３５〜１４０°Ｃで８時間攪拌した。反応終了後、
室温まで冷却し、析出した結晶をメタノールで洗浄した
後、ニトロベンゼンから再結晶し、青色結晶性粉末とし
て融点３００°Ｃ以上の化合物１．７４ ｇ （収率８
５％）を得た。[Synthesis Example 2] 5,7.12.14-tetrahydro-5,12-dimethyl-7,14-dinanomethylene-quino[2,3-b]
Synthesis of acridine (compound 2) 5.12. -dihydro-5,12-dimethyl-quino[2
, 3-bl acridine-7,14-dione (1.6 g) and malononitrile (6.2 g) were added to 500 mj' of acetic anhydride and stirred at 135-140°C for 8 hours. After the reaction is complete,
After cooling to room temperature and washing the precipitated crystals with methanol, they were recrystallized from nitrobenzene to obtain 1.74 g of a compound with a melting point of 300°C or higher as a blue crystalline powder (yield: 8
5%).
〔合成例３〕
５、７．１２．１４−テトラヒドロ−５，１２−ジブチ
ル−７、＋４−ジシアノメチレン−キノ［２，３−ｂ］
アクリジン（化合物Ｎα４）の合成
５．１２．−ジヒドロ−５，１２−ジブチル−キノ［２
，３−ｂｌアクリジン−７，１４−ジオン１．２ｇ、マ
ロノニトリル３．７ｇ、無水酢酸３０ｍ１をＮ−メチル
ピロリドン２５０ｍ１に添加し、 １３５〜１４０℃で
２０時間攪拌した。反応終了後、室温まで冷却し、析出
した結晶をメタノールで洗浄した後、ピリジンから再結
晶し、青色結晶性粉末として融点３００°Ｃ以上の化合
物１．１５ｇ（収率７８％）を得た。[Synthesis Example 3] 5,7.12.14-tetrahydro-5,12-dibutyl-7,+4-dicyanomethylene-quino[2,3-b]
Synthesis of acridine (compound Nα4) 5.12. -dihydro-5,12-dibutyl-quino[2
, 3-bl acridine-7,14-dione (1.2 g), malononitrile (3.7 g), and acetic anhydride (30 ml) were added to N-methylpyrrolidone (250 ml) and stirred at 135 to 140°C for 20 hours. After the reaction was completed, the mixture was cooled to room temperature, the precipitated crystals were washed with methanol, and then recrystallized from pyridine to obtain 1.15 g (yield: 78%) of a blue crystalline powder having a melting point of 300°C or higher.
（合成例４〕
５、７．１２．１４−テトラヒドロ−５，１２−ジブチ
ル−３，１０−シクロローフ、１４−ジシアノメチレン
−キノ［２，３−ｂｌアクリジン（化合物Ｎα６）の合
成
５．１２−ジヒドロ−５，１２−ジブチル−３，１叶ジ
クロロ−キノ［２，３−ｂｌアクリジン−７，１４−ジ
オンｉ、ｏｇ、マロノニトリル２．７ｇをプロピオン酸
無水物３＋Ｗに添加し、 １６０−１６５°Ｃで３時間
攪拌した。反応終了後、室温まで冷却し、析出した結晶
をメタノールで洗浄した後、ニトロベンゼンから再結晶
し、青色結晶性粉末として融点２６４〜２６５℃の化合
物０．９０ｇ （収率７５％）を得た。(Synthesis Example 4) Synthesis of 5,7.12.14-tetrahydro-5,12-dibutyl-3,10-cyclolophe, 14-dicyanomethylene-quino[2,3-bl acridine (compound Nα6) 5.12- Dihydro-5,12-dibutyl-3,1-dichloro-quino[2,3-bl acridine-7,14-dione i,og, 2.7 g of malononitrile was added to propionic anhydride 3+W at 160-165° The mixture was stirred for 3 hours at C. After the reaction was completed, it was cooled to room temperature, and the precipitated crystals were washed with methanol and then recrystallized from nitrobenzene to give 0.90 g of a compound with a melting point of 264 to 265 °C as a blue crystalline powder (yield 75%).
〔合成例５〕
５、７．１２．１４−テトラヒドロキノ−５，１２−ジ
ブチル−２，９−ジメチル−７，１４−ジシアノメチレ
ン−キノ［２，３−ｂｌアクリジン（化合物Ｎα７）の
合成５．１２−ジヒドロ−５，１２−ジブチル−２，９
−ジメチルーキ／ ［２，３−ｂ］ ７クリジ：／−７
，１４−ジオン０．８ｇ、 ７０ノ二トリル２．３ｇを
無水酢酸４０ｍ１に添加し、１３５〜１４０℃で９時間
攪拌した。反応終了後、室温まで冷却し、析出した結晶
をメタノールて洗浄した後、ニトロベンゼンから再結晶
し、青色結晶性粉末として融点３００°Ｃ以上の化合物
０．８９ｇ （収率９２％）を得た。[Synthesis Example 5] Synthesis of 5,7.12.14-tetrahydroquino-5,12-dibutyl-2,9-dimethyl-7,14-dicyanomethylene-quino[2,3-bl acridine (compound Nα7) 5 .12-dihydro-5,12-dibutyl-2,9
-dimethyluki/[2,3-b] 7kuriji:/-7
, 0.8 g of 14-dione and 2.3 g of 70-nonitrile were added to 40 ml of acetic anhydride, and the mixture was stirred at 135 to 140°C for 9 hours. After the reaction was completed, the mixture was cooled to room temperature, and the precipitated crystals were washed with methanol and then recrystallized from nitrobenzene to obtain 0.89 g (yield: 92%) of a blue crystalline powder having a melting point of 300°C or higher.
本発明の方法によって合成したテトラヒドロキナクリジ
ン誘導体を表１に示す。Table 1 shows the tetrahydroquinacridine derivatives synthesized by the method of the present invention.
（以下余白）
比較化合物
実施例１．耐光性および耐熱性試験
得られたテトラヒドロキナクリジン誘導体について、耐
光性および耐熱性を調へ、他の高級赤色顔料であるキナ
クリドン（大日本インキ化学工業■製）比較化合物［１
］ と比較した。(Left below) Comparative Compound Example 1. Light resistance and heat resistance test The light resistance and heat resistance of the obtained tetrahydroquinacridine derivative were tested using another high-grade red pigment, quinacridone (manufactured by Dainippon Ink & Chemicals) [1].
] compared with.
１） ５．７．１２．１４−テトラヒドロ−５，１２−
ジメチル−７，１４−ジシアノメチレン−キノ［２，３
−ｂ］アクリジン（化合物嵐２）をメラミンアルキド樹
脂で塗料化し、アルミ板上に展色して試料とし、アトラ
スウエザオメーター０１３５により。耐光性試験を行っ
た。４５０時間という過酷な条件下で試験し、グレース
ケールで判定した結果、化合物Ｎα２の耐光性はキナク
リドン顔料とほぼ同等以上であることか明らかになった
（表２）。1) 5.7.12.14-tetrahydro-5,12-
Dimethyl-7,14-dicyanomethylene-quino[2,3
-b] Acridine (Compound Arashi 2) was made into a paint using melamine alkyd resin, spread on an aluminum plate, and used as a sample, and measured using an Atlas Weatherometer 0135. A light resistance test was conducted. As a result of testing under harsh conditions of 450 hours and judging on a gray scale, it became clear that the light resistance of compound Nα2 was almost equal to or better than that of quinacridone pigments (Table 2).
２） ５．７．１２．１４−テトラヒドロ−５，１２−
ジメチル−７，１４−ジシアノメチレン−キノ［２，３
−ｂ］アクリジン（化合物Ｎα２）の耐熱挙動をキナク
リドン顔料と比較するため、示差熱重量分析（ＤＴＡ、
ＴＧＡ ’）を行なった。測定は、顔料の実用上から空
気中で行い、測定機器はマッグ・サイエンスＴＧ−ＤＴ
Ａ ２０００型を使用した。試料は、白金皿上にｌＯ〜
１５■秤量し、開放状態で室温から７００°Ｃまて１５
℃／ｍｉｎて昇温して熱分解曲線図１および図２を得た
。その結果、化合物Ｎα２は、キナクリドン顔料と比較
し、約３４５℃から熱変化をうけることか明らかになっ
た。顔料の実用耐熱性を問題にする場合、その温度はせ
いぜい３００°Ｃまでと考えられており、化合物淘２が
３２０°Ｃまてまったく重量変化を受けていないことか
ら、耐熱性に優れていることか明らかになりた。2) 5.7.12.14-tetrahydro-5,12-
Dimethyl-7,14-dicyanomethylene-quino[2,3
-b] In order to compare the heat resistance behavior of acridine (compound Nα2) with that of quinacridone pigment, differential thermogravimetric analysis (DTA),
TGA') was performed. Measurements are carried out in the air for practical purposes, and the measuring equipment is Mag Science TG-DT.
A 2000 model was used. The sample was placed on a platinum plate at lO~
15 ■Weigh and heat from room temperature to 700°C in an open state.15
The temperature was increased at a rate of .degree. C./min to obtain thermal decomposition curves in FIGS. 1 and 2. As a result, it was revealed that compound Nα2 undergoes thermal changes from about 345° C. compared to quinacridone pigments. When considering the practical heat resistance of pigments, it is thought that the temperature is at most 300°C, and Compound 2 shows no weight change at 320°C, so it has excellent heat resistance. It became clear.
更にメラミンアルキド樹脂での耐熱性試験（２００”Ｃ
，３０分）を行い、変進色度をグレースケールで判定し
た（表２）。 その結果、２００°Ｃにおける化合物Ｎ
α２の耐熱性は、キナクリドン顔料とほぼ同等以上であ
ることか明らかになった。Furthermore, heat resistance test with melamine alkyd resin (200”C
, 30 minutes), and the changing chromaticity was determined on a gray scale (Table 2). As a result, the compound N at 200°C
It has become clear that the heat resistance of α2 is almost equal to or better than that of quinacridone pigments.
表２．耐光性および耐熱性試験結果Table 2. Light resistance and heat resistance test results
図１は本発明による化合物Ｎα２の耐熱挙動を示すグラ
フ、図２は市販のキナクリドン顔料の耐熱挙動を示すグ
ラフである。
代理人 弁理士（６６４２） 萩 野 千 パ
ゝ−一て
（ほか３名）
Ｔ Ｇ （’１０）FIG. 1 is a graph showing the heat resistance behavior of the compound Nα2 according to the present invention, and FIG. 2 is a graph showing the heat resistance behavior of a commercially available quinacridone pigment. Agent Patent Attorney (6642) Chi Hagino Pai-Itte (and 3 others) TG ('10)
Claims (1)
ゲン原子、アルキル基、アルコキシ基を表わし、Ｒ＿１
、Ｒ＿２およびＲ＿３は同一でも異なってもよい。Ｒ＿
４、Ｒ＿５はそれぞれ水素原子、アルキル基、アルケニ
ル基、アラルキル基およびアリール基を表わし、Ｒ＿４
およびＲ＿５は同一でも異なってもよい。） で表わされるテトラヒドロキナクリジン誘導体。 ２）一般式［２］ ▲数式、化学式、表等があります▼［２］ （式中、Ｒ＿１、Ｒ＿２およびＲ＿３は水素原子、ハロ
ゲン原子、アルキル基、アルコキシ基を表わし、Ｒ＿１
、Ｒ＿２およびＲ＿３は同一でも異なってもよい。Ｒ＿
４、Ｒ＿５はそれぞれ水素原子、アルキル基、アルケニ
ル基、アラルキル基およびアリール基を表わし、Ｒ＿４
およびＲ＿５は同一でも異なってもよい。） で表わされるキナクリドン誘導体をマロニトリルと反応
させることを特徴とする 一般式［１］ ▲数式、化学式、表等があります▼［１］ （式中、Ｒ＿１、Ｒ＿２、Ｒ＿３、Ｒ＿４およびＲ＿５
は前記の意味を持つ。） で表わされるテトラヒドロキナクリジン誘導体の製造法
。[Claims] 1) General formula [1] ▲ Numerical formulas, chemical formulas, tables, etc. ▼ [1] (In the formula, R_1, R_2 and R_3 represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, R_1
, R_2 and R_3 may be the same or different. R_
4, R_5 each represent a hydrogen atom, an alkyl group, an alkenyl group, an aralkyl group, and an aryl group, and R_4
and R_5 may be the same or different. ) A tetrahydroquinacridine derivative represented by 2) General formula [2] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [2] (In the formula, R_1, R_2 and R_3 represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, and R_1
, R_2 and R_3 may be the same or different. R_
4, R_5 each represent a hydrogen atom, an alkyl group, an alkenyl group, an aralkyl group, and an aryl group, and R_4
and R_5 may be the same or different. ) General formula [1] characterized by reacting a quinacridone derivative represented by
has the above meaning. ) A method for producing a tetrahydroquinacridine derivative represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2275286A JP3000110B2 (en) | 1990-10-16 | 1990-10-16 | Tetrahydroquinacridine derivative and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2275286A JP3000110B2 (en) | 1990-10-16 | 1990-10-16 | Tetrahydroquinacridine derivative and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04154780A true JPH04154780A (en) | 1992-05-27 |
| JP3000110B2 JP3000110B2 (en) | 2000-01-17 |
Family
ID=17553311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2275286A Expired - Fee Related JP3000110B2 (en) | 1990-10-16 | 1990-10-16 | Tetrahydroquinacridine derivative and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3000110B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102060854A (en) * | 2010-11-25 | 2011-05-18 | 吉林大学 | Nitrile substituted quinacridone compounds and application thereof in organic solar cell |
-
1990
- 1990-10-16 JP JP2275286A patent/JP3000110B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102060854A (en) * | 2010-11-25 | 2011-05-18 | 吉林大学 | Nitrile substituted quinacridone compounds and application thereof in organic solar cell |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3000110B2 (en) | 2000-01-17 |
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