JPH0218460A - Production of quinophthalone pigment - Google Patents
Production of quinophthalone pigmentInfo
- Publication number
- JPH0218460A JPH0218460A JP16739488A JP16739488A JPH0218460A JP H0218460 A JPH0218460 A JP H0218460A JP 16739488 A JP16739488 A JP 16739488A JP 16739488 A JP16739488 A JP 16739488A JP H0218460 A JPH0218460 A JP H0218460A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- pigment
- quinophthalone
- following formula
- 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
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000000049 pigment Substances 0.000 title abstract 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims abstract description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- 150000002989 phenols Chemical class 0.000 claims abstract description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 2
- 238000000859 sublimation Methods 0.000 abstract description 2
- 230000008022 sublimation Effects 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- -1 T-methoxyamine Chemical compound 0.000 description 9
- 239000013078 crystal Substances 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 3
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- JPBLHOJFMBOCAF-UHFFFAOYSA-N 1,3-benzoxazol-2-amine Chemical compound C1=CC=C2OC(N)=NC2=C1 JPBLHOJFMBOCAF-UHFFFAOYSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- WNHJODQFRPJHCO-UHFFFAOYSA-N 1-hexadecyl-3-phenylurea Chemical compound CCCCCCCCCCCCCCCCNC(=O)NC1=CC=CC=C1 WNHJODQFRPJHCO-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- KURRHYKFNUZCSJ-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethanamine Chemical compound CCOCCOCCN KURRHYKFNUZCSJ-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- RGDQRXPEZUNWHX-UHFFFAOYSA-N 3-methylpyridin-2-amine Chemical compound CC1=CC=CN=C1N RGDQRXPEZUNWHX-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- GGWJFTHFCOPBSY-UHFFFAOYSA-N 4-nitro-1,3-thiazol-2-amine Chemical compound NC1=NC([N+]([O-])=O)=CS1 GGWJFTHFCOPBSY-UHFFFAOYSA-N 0.000 description 1
- FDECURPHVMNAKO-UHFFFAOYSA-N 4-nonylaniline Chemical compound CCCCCCCCCC1=CC=C(N)C=C1 FDECURPHVMNAKO-UHFFFAOYSA-N 0.000 description 1
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 1
- BGNLXETYTAAURD-UHFFFAOYSA-N 4-tert-butylcyclohexan-1-amine Chemical compound CC(C)(C)C1CCC(N)CC1 BGNLXETYTAAURD-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical compound C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- UZCXPYDBYUEZCV-UHFFFAOYSA-N methyl 3-aminopropanoate Chemical compound COC(=O)CCN UZCXPYDBYUEZCV-UHFFFAOYSA-N 0.000 description 1
- IAGUPODHENSJEZ-UHFFFAOYSA-N methyl n-phenylcarbamate Chemical compound COC(=O)NC1=CC=CC=C1 IAGUPODHENSJEZ-UHFFFAOYSA-N 0.000 description 1
- FUPMLXVNXBAYIE-UHFFFAOYSA-N n,n-bis(ethylamino)aniline Chemical compound CCNN(NCC)C1=CC=CC=C1 FUPMLXVNXBAYIE-UHFFFAOYSA-N 0.000 description 1
- QDTDFSFRIDFTCF-UHFFFAOYSA-N n-phenyl-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1NC1=CC=CC=C1 QDTDFSFRIDFTCF-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- 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、カラー液晶用２色性色素（例えば、特開昭５
９−３６１８１ 、特開昭５８−５３９７９） 、偏光
板用色素（例えば、特開昭６２−２７０６６４）、昇華
転写記録用色素などに用いられるキノフタロン色素の製
造方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention is directed to dichroic dyes for color liquid crystals (for example,
9-36181, JP-A-58-53979), a method for producing quinophthalone dyes used in dyes for polarizing plates (e.g., JP-A-62-270664), sublimation transfer recording dyes, and the like.
下式（ＩＶ）
〔式（［Ｖ）中、Ｙｌ、Ｙ２、Ｙ″、 Ｙ“及びｙｓは
各々独立に水素原子、アルキル基、アミノ基、アルキル
アミノ基、水酸基、アルコキシ基、またはハロゲン原子
を表わし、Ｒは置換又は無置換のアルキル基、環状アル
キル基、アリール基又は複素環を表す、）で示される色
素の製造方法は、特開昭６２−２７５１６３及び特開昭
６３−３０５６３に示される様にメタノール、ブタノー
ル、エチレングリコールなどのアルコール溶媒、ベンゼ
ン、クロルベンゼン、ニトロベンゼンなどの芳香族非プ
ロトン溶媒、アミド系溶媒中で５０〜２００°Ｃの温度
で、下式（Ｉ）〔式（Ｉ）中、ｖＩ、 ｙｔ、Ｙ３、ｖ
４、及びｙｓは式（ＩＶ）のｙｔ、 ｙｔ、 Ｙ：ｌ、
Ｙ４及びＹ５と同一の意味を表す。〕で示されるキノフ
タロン−ジカルボン酸無水物と下式（ｎ）
Ｒ−Ｎ１３ （ｔｌ ）
〔式（ＴＩ）中、Ｒは式（ＩＶ）中のＲと同一の意味を
表す。〕
で示されるアミンを反応する方法がとられている。The following formula (IV) [In formula ([V), Yl, Y2, Y'', Y'' and ys each independently represent a hydrogen atom, an alkyl group, an amino group, an alkylamino group, a hydroxyl group, an alkoxy group, or a halogen atom] The method for producing the dye represented by the following formula (wherein R represents a substituted or unsubstituted alkyl group, cyclic alkyl group, aryl group, or heterocycle) is disclosed in JP-A-62-275163 and JP-A-63-30563. Similarly, the following formula (I) [Formula (I ) medium, vI, yt, Y3, v
4, and ys are yt of formula (IV), yt, Y:l,
It has the same meaning as Y4 and Y5. Quinophthalone-dicarboxylic acid anhydride represented by the following formula (n) R-N13 (tl) [In the formula (TI), R represents the same meaning as R in the formula (IV). ] A method has been adopted in which the amine shown in the following is reacted.
しかし、原料のキノフタロン−ジカルボン酸無水物が前
記の溶媒に不溶であるし、又前記溶媒中では反応活性が
低く、未反応物が多く残ったり、高温反応を行うと副生
物が多量に生成するという欠点があった。However, the raw material, quinophthalone-dicarboxylic anhydride, is insoluble in the above-mentioned solvents, and the reaction activity is low in the above-mentioned solvents, resulting in a large amount of unreacted substances remaining and large amounts of by-products being produced when the reaction is carried out at high temperatures. There was a drawback.
本発明者らは、鋭意検討の結果、下式（ＩＩＩ）〔式（
ｌｉｔ）中、ｘＩ、 ｘＺ、Ｘ３、×４及びＸ’は各１
に立に水素原子、アルキル基またはハロゲン原子を表す
、〕
で示されるフェノール類を溶媒として、キノリン、イソ
キノリン、ピリジン、モノアルキルピリジン、ジアルキ
ルピリジン、又はトリアルキルピリジンの存在下又は不
存在下に、式（Ｉ）のキノフタロン−ジカルボン酸無水
物と式（ｎ）のアミンを反応すると高い収率で式（ＩＶ
）のキノフタロン色素が得られることを見出し、本発明
を達成した。As a result of intensive studies, the present inventors have determined that the following formula (III) [Formula (
lit), xI, xZ, X3, x4 and X' are each 1
in the presence or absence of quinoline, isoquinoline, pyridine, monoalkylpyridine, dialkylpyridine, or trialkylpyridine, using a phenol represented by ] as a solvent, Quinophthalone-dicarboxylic anhydride of formula (I) and amine of formula (n) are reacted to form formula (IV) in high yield.
) was found to be able to obtain a quinophthalone dye, and the present invention was achieved.
式（Ｉ）中、Ｙｌ、Ｙ２、ｖ３、Ｙ４及び’ｌ””ｅｘ
＜される置換基の例としては、Ｈ；−ＣＨｔ３ 、＝Ｃ
ＣＨｓ 。In formula (I), Yl, Y2, v3, Y4 and 'l""ex
Examples of substituents include H;-CHt3, =C
CHs.
−（Ｃ１ｂ） ｚｃＬ、−ＣＨ（ＣＨｓ） ｚ 、−（
ＣＨｔ） ５ｃＨｓ、−ＣＨｚＣＨ（ＣＨｉｈ、−ＣＨ
（ＣＨｚ）ＣｔＨｓ、−（ＣＨｘｌａＣＨｉ、（ＣＨｚ
） ５ＣＨｓ、−（ｃｕｔ） ＆ＣＨ３、−（Ｃｔｌ
ｔ） ｔｃ）Ｉ ３等のアルキル基； −０ＣＨｉ 、
−０ＣＪｓ、−ｏ（ｃ）Ｉｚ） ２Ｃ１１２，０（ＣＨ
ｚ） ３ＣＨ！ 、−０（ＣＩｌｚ） ａｃＨｊ等のア
ルコキシ基；Ｃ１，Ｂｒ、、ｌ 、 Ｆ 、−１ｔＨ
ｃＨ３、−ＮＨＣ２１１５、−Ｎ（ＣＨ３） ！、４（
ＣＪｓ）ｇなどが挙げられる。-(C1b) zcL, -CH(CHs) z, -(
CHt) 5cHs, -CHzCH(CHih, -CH
(CHz)CtHs, -(CHxlaCHi, (CHz
) 5CHs, -(cut) &CH3, -(Ctl
t) tc) Alkyl group such as I 3; -0CHi,
-0CJs, -o(c)Iz) 2C112,0(CH
z) 3CH! , -0(CIlz) acHj and other alkoxy groups; C1, Br,, l, F, -1tH
cH3, -NHC2115, -N(CH3)! , 4(
Examples include CJs)g.
式（Ｉｆ）で示される置換又は無置換のアルキルアミン
の例としては、メチルアミン、エチルアミン、プロピル
アミン、ブチルアミン、オクチルアミン、Ｔ−メトキシ
アミン、エトキシエトキシエチルアミン、β−クロルア
ミン、β−メトキシカルボニルエチルアミン、Ｎ、Ｎ−
ジメチルアミノエチルアミンなどが挙げられ、置換又は
無置換のシクロアルキルアミンの例としては、シクロア
ルキルアミン、４ｔｅｒｔ−ブチルシクロヘキシルアミ
ン、４−ｔｒａｎａ−アミルシクロヘシキルアミン、シ
クロペンチルアミンなどが挙げられ、置換又は無置換の
アリールアミンの例としては、アニリン、トルイジン、
エチルアニリン、メトキシカルボニルアニリン、ニトロ
アニリン、ｐ−ノニルアニリン、セチルアミノカルボニ
ルアニリン、ペンチジン、ベンゾオキサゾイルアニリン
、アミノアゾベンゼン、ベンゾチアゾリルアニリン、ト
リジン、Ｎ、Ｎ−ジエチルアミノアニリン、オクチルオ
キシカルボニルフェニルアニリン、ベンゾオキサゾイル
ビフェニルアミン、ビフェニルアミンなどのアニリン誘
導体、ナフチルアミン、アルキルナフチルアミン、アミ
ノアントラキノン、アミノアントラセンなどの縮合多環
式アミンなどが挙げられ、複素環アミンの例としては、
チオフェンアミン、ベンゾチアゾールアミン、ニトロチ
アゾールアミン、ベンゾオキサゾールアミン、ピリジン
アミン、メチルピリジンアミンなどが挙げられる。Examples of the substituted or unsubstituted alkylamine represented by formula (If) include methylamine, ethylamine, propylamine, butylamine, octylamine, T-methoxyamine, ethoxyethoxyethylamine, β-chloramine, β-methoxycarbonylethylamine. , N, N-
Examples of substituted or unsubstituted cycloalkylamines include cycloalkylamine, 4tert-butylcyclohexylamine, 4-trana-amylcyclohexylamine, and cyclopentylamine. Examples of unsubstituted arylamines include aniline, toluidine,
Ethylaniline, methoxycarbonylaniline, nitroaniline, p-nonylaniline, cetylaminocarbonylaniline, pentidine, benzoxazoylaniline, aminoazobenzene, benzothiazolylaniline, tolidine, N,N-diethylaminoaniline, octyloxycarbonylphenylaniline , benzoxazoyl biphenylamine, aniline derivatives such as biphenylamine, fused polycyclic amines such as naphthylamine, alkylnaphthylamine, aminoanthraquinone, aminoanthracene, etc. Examples of heterocyclic amines include:
Examples include thiopheneamine, benzothiazolamine, nitrothiazoleamine, benzoxazoleamine, pyridineamine, methylpyridineamine, and the like.
又、式（ＩＩＩ）で示されるフェノール誘導体の例とし
ては、フェノール、０−クロルフェノール、ｍ−クロル
フェノール、ｐ−クロルフェノール、０−クレゾール、
ｍ−クレゾール、ｐ−クレゾール、エチルフェノール、
ブチルフェノールなどが挙げられる。Examples of the phenol derivative represented by formula (III) include phenol, 0-chlorophenol, m-chlorophenol, p-chlorophenol, 0-cresol,
m-cresol, p-cresol, ethylphenol,
Examples include butylphenol.
反応条件としては、一般弐Ｎ）で示されるキノフタロン
−ジカルボン酸無水物１モルに対して、アミン類０．７
〜２．０モルが好ましく、又、溶媒として用いるフェノ
ール誘導体は、５〜２０００モルが好ましく、触媒とし
てキノリン、イソキノリン、ピリジン及びそれらの誘導
体を用いる場合は、０．００５〜５モル比を用いるのが
好ましい。The reaction conditions were as follows: 0.7 amines per mol of quinophthalone dicarboxylic anhydride represented by 2N)
-2.0 mol is preferable, and the phenol derivative used as a solvent is preferably 5-2000 mol, and when using quinoline, isoquinoline, pyridine and their derivatives as a catalyst, a molar ratio of 0.005-5 is used. is preferred.
反応温度としては、５０〜２００″Ｃが好ましく、反応
時間としては１〜３０時間が好ましい。The reaction temperature is preferably 50 to 200''C, and the reaction time is preferably 1 to 30 hours.
尚、触媒としてキノリン、イソキノリン及びピリジン類
を用いると分子間イミド化を抑制し、より高純度の化合
物（ＩＶ）が得られる。特に効果が顕著となるのはアリ
ールアミン類、複素環アミンｌｆｆ１導体のイミドの場
合である。Incidentally, when quinoline, isoquinoline and pyridine are used as catalysts, intermolecular imidization is suppressed and a higher purity compound (IV) can be obtained. The effect is particularly remarkable in the case of imides of arylamines and heterocyclic amines lff1 conductors.
以下、実施例により本発明の詳細な説明する。 Hereinafter, the present invention will be explained in detail with reference to Examples.
実施例１ 下式で示される酸無水物３５９ ｇ 。Example 1 359 g of acid anhydride represented by the following formula.
２−アミノナフタレン１４３ ｇ 、イソキノリン１３
０ｇおよびメタクレゾールＬｉの混合物を１５０’Ｃで
４時間加熱攪拌した０反応液を室温に冷却して析出した
結晶を濾過、メタノールで洗浄し、乾燥した。2-aminonaphthalene 143 g, isoquinoline 13
A mixture of Li and meta-cresol Li was heated and stirred at 150'C for 4 hours. The reaction mixture was cooled to room temperature, and the precipitated crystals were filtered, washed with methanol, and dried.
収量４００ ｇ 、 此の結晶はＩＲ，ＮＭＲより下
記化合物と同定され、液体クロマトグラフにより純度９
５％であることが判った。The yield was 400 g. The crystals were identified as the following compound by IR and NMR, and the purity was 9 by liquid chromatography.
It was found to be 5%.
実施例３
下記式で示されるカルボン酸無水物３７３ｇ、実施例２
下式で示される酸無水物４３８ｇ、
ｐ−フェニルアニリン１６７ ｇ 、キノリン１００
ｇ オよび０−クロロフェノールｌｉの混合物を２００
℃で６時間加熱撹拌した０反応液を室温に冷却して析出
した結晶を濾過、メタノールで洗浄し、乾燥した。収量
４５０ ｇ、此の結晶は下式の化合物であり純度は９６
％であった。Example 3 373 g of a carboxylic acid anhydride represented by the following formula, Example 2 438 g of an acid anhydride represented by the following formula, 167 g of p-phenylaniline, 100 g of quinoline
200 g of a mixture of O and O-chlorophenol
The reaction mixture was heated and stirred at ℃ for 6 hours and cooled to room temperature, and the precipitated crystals were filtered, washed with methanol, and dried. Yield: 450 g. This crystal is a compound of the following formula, and its purity is 96.
%Met.
２．６−ジアミツアントラキノン１６９ ｇ 、イソキ
ノリン６０ｇとｐ−クレゾール３０００ ｇの混合物を
２００℃にて１０時間加熱攪拌した０反応液を室温に冷
却して析出した結晶を濾過、メタノールで洗浄し、乾燥
した。収゛量４００ ｇ、此の結晶は下式の化合物であ
り純度は９４％であった。A mixture of 169 g of 2.6-diamithanthraquinone, 60 g of isoquinoline, and 3000 g of p-cresol was heated and stirred at 200°C for 10 hours. The reaction solution was cooled to room temperature, and the precipitated crystals were filtered and washed with methanol. Dry. The yield was 400 g, and the crystals were a compound of the following formula, with a purity of 94%.
実施例４〜１９ 下記−殺伐に従って、 表１に示すＸｌ Ｒの化合 物を合成した。Examples 4-19 Below - according to the murderous Xl shown in Table 1 Combination of R synthesized things.
結果を表１に記す。The results are shown in Table 1.
Claims (1)
びＹ＾５は各々独立に水素原子、アルキル基、アミノ基
、アルキルアミノ基、水酸基、アルコキシ基またはハロ
ゲン原子を表す。〕 で示されるキノフタロン−ジカルボン酸無水物と下式（
II） Ｒ−ＮＨ＿２（II） 〔式（II）中、Ｒは置換又は無置換のアルキル基、環状
アルキル基、アリール基又は複素環を表す。〕で示され
るアミン類を下式（III） ▲数式、化学式、表等があります▼（III） 〔式（III）中、Ｘ＾１、Ｘ＾２、Ｘ＾３、Ｘ＾４及び
Ｘ＾５は各々独立に水素原子、アルキル基、またはハロ
ゲン原子を表す。〕 で示されるフェノール誘導体中、キノリン、イソキノリ
ン、ピリジン、モノアルキルピリジン、ジアルキルピリ
ジン、又はトリアルキルピリジンの存在下又は不存在下
に加熱反応することを特徴とする下式（IV） ▲数式、化学式、表等があります▼（IV） 〔式（IV）中、Ｙ＾１、Ｙ＾２、Ｙ＾３、Ｙ＾４及びＹ
＾５は式（ I ）のＹ＾１、Ｙ＾２、Ｙ＾３、Ｙ＾４及
びＹ＾５と同一の基を意味し、Ｒは式（II）のＲと同一
の意味を表す。〕 で示されるキノフタロン色素の製造方法。[Claims] 1) The following formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In formula (I), Y^1, Y^2, Y^3, Y^4, and Y^5 each independently represents a hydrogen atom, an alkyl group, an amino group, an alkylamino group, a hydroxyl group, an alkoxy group, or a halogen atom. ] Quinophthalone-dicarboxylic acid anhydride represented by the following formula (
II) R-NH_2(II) [In formula (II), R represents a substituted or unsubstituted alkyl group, cyclic alkyl group, aryl group, or heterocycle. ] Amines represented by the following formula (III) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (III) [In formula (III), X^1, X^2, X^3, X^4 and X^ Each of 5 independently represents a hydrogen atom, an alkyl group, or a halogen atom. ] The following formula (IV) characterized by a heating reaction in the presence or absence of quinoline, isoquinoline, pyridine, monoalkylpyridine, dialkylpyridine, or trialkylpyridine in the phenol derivative represented by ▲Mathematical formula, chemical formula , tables, etc.▼(IV) [In formula (IV), Y^1, Y^2, Y^3, Y^4 and Y
^5 means the same group as Y^1, Y^2, Y^3, Y^4 and Y^5 in formula (I), and R represents the same meaning as R in formula (II). ] A method for producing a quinophthalone dye.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16739488A JPH0619035B2 (en) | 1988-07-05 | 1988-07-05 | Method for producing quinophthalone dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16739488A JPH0619035B2 (en) | 1988-07-05 | 1988-07-05 | Method for producing quinophthalone dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0218460A true JPH0218460A (en) | 1990-01-22 |
| JPH0619035B2 JPH0619035B2 (en) | 1994-03-16 |
Family
ID=15848887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16739488A Expired - Lifetime JPH0619035B2 (en) | 1988-07-05 | 1988-07-05 | Method for producing quinophthalone dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0619035B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109970636A (en) * | 2019-03-11 | 2019-07-05 | 山西大学 | The method of ONOO- spectral probe and preparation method and ultraviolet-visible absorption spectroscopy, fluorescence spectrometry ONOO- |
| CN110041254A (en) * | 2018-01-15 | 2019-07-23 | 保土谷化学工业株式会社 | Yellow based compound, the coloured composition containing the compound, colour filter colorant and colour filter |
-
1988
- 1988-07-05 JP JP16739488A patent/JPH0619035B2/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110041254A (en) * | 2018-01-15 | 2019-07-23 | 保土谷化学工业株式会社 | Yellow based compound, the coloured composition containing the compound, colour filter colorant and colour filter |
| KR20190087301A (en) * | 2018-01-15 | 2019-07-24 | 호도가야 가가쿠 고교 가부시키가이샤 | Yellow compound, coloring composition containing the compound, coloring agent for color filter and color filter |
| JP2019123856A (en) * | 2018-01-15 | 2019-07-25 | 保土谷化学工業株式会社 | Yellow compound, coloring composition containing the compound, colorant for color filters and color filter |
| TWI796403B (en) * | 2018-01-15 | 2023-03-21 | 日商保土谷化學工業股份有限公司 | Yellow compound, coloring composition containing the compound, coloring agent for color filter and color filter |
| CN109970636A (en) * | 2019-03-11 | 2019-07-05 | 山西大学 | The method of ONOO- spectral probe and preparation method and ultraviolet-visible absorption spectroscopy, fluorescence spectrometry ONOO- |
| CN109970636B (en) * | 2019-03-11 | 2022-05-20 | 山西大学 | ONOO-spectrum probe and preparation method thereof, and method for measuring ONOO-by ultraviolet visible absorption spectrum and fluorescence spectrum |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0619035B2 (en) | 1994-03-16 |
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