JPH0216165A - Preparation of perylene coloring matter - Google Patents
Preparation of perylene coloring matterInfo
- Publication number
- JPH0216165A JPH0216165A JP16499888A JP16499888A JPH0216165A JP H0216165 A JPH0216165 A JP H0216165A JP 16499888 A JP16499888 A JP 16499888A JP 16499888 A JP16499888 A JP 16499888A JP H0216165 A JPH0216165 A JP H0216165A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- alkyl group
- amount
- alkyl
- 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 title claims abstract description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 238000004040 coloring Methods 0.000 title abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- 150000002989 phenols Chemical class 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 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
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims 1
- -1 cyclic alkyl Chemical group 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 7
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 abstract description 5
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 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
- GUUUPLGXSAZRQX-UHFFFAOYSA-N 1-ethyl-1-(2-ethylphenyl)hydrazine Chemical compound CCN(N)C1=CC=CC=C1CC GUUUPLGXSAZRQX-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
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-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
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-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
- 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
- RJUUGFFTSOCZNK-UHFFFAOYSA-N CCCCCCCCCCCCCCCCN(C(N)=O)C1=CC=CC=C1 Chemical compound CCCCCCCCCCCCCCCCN(C(N)=O)C1=CC=CC=C1 RJUUGFFTSOCZNK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001408 amides 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
- 239000000010 aprotic solvent Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229940100630 metacresol Drugs 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
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-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
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation 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
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、染料（例えば、カラーインデックスｋ Ｖａ
ｔ Ｒｅｄ２３．２９） 、顔料（例えば、カラーイン
デックスＮｌｌｌＰＮ１１ｌＰｉ Ｒｅｄ １２３．１
７９．１８９．１９０）、有機光電材（電荷発生材）（
池森編著 特殊機能性色素ＣＭＣＰＩ、Ｐ１２７）、偏
光板用色素（例えば、水田監修 偏光フィルムの応用Ｃ
ＭＣＰ＋、Ｐ５６） 、昇華転写記録用色素などに用い
られるペリレン色素の製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention provides dyes (for example, color index k Va
t Red23.29), pigment (e.g. color index NlllPN11lPi Red 123.1
79.189.190), organic photoelectric materials (charge generating materials) (
Special functional dye CMCPI, P127, edited by Ikemori, Pigment for polarizing plates (for example, Polarizing film application C, supervised by Mizuta)
MCP+, P56), relates to a method for producing perylene dyes used for sublimation transfer recording dyes, etc.
下式（ＩＶ）
〔式（ｒＶ）中、Ｙは水素原子、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、ハロゲン
原子を表し、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５７−７４３６１
及び特開昭５７−１６７３５２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
’ｔ８ 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）容媒中で５
０〜２００°Ｃの温度で、下式（＋）（ＩＶ）
〔式（Ｉ）中、Ｙは式（ｒＶ）中のＹと同一の意味を表
す。〕
で示されるペリレンテトラカルボン酸無水物と下式（ｎ
）
Ｒ−ＮＨ！ （ｎ）
〔式（ＩＩ）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 the formula (rV), Y represents a hydrogen atom, an alkyl group, an amino group, an alkylamino group, a hydroxyl group, an alkoxy group, or a halogen atom, and R represents a substituted or unsubstituted alkyl group or a cyclic alkyl group , represents an aryl group or a heterocycle. ] The method for producing the dye shown in
and as shown in JP-A No. 57-167352, in an alcohol medium such as methanol, butanol or ethylene glycol, an aromatic aprotic solvent such as benzene, chlorobenzene or nitrobenzene, or an amide type medium).
At a temperature of 0 to 200°C, the following formula (+) (IV) [In formula (I), Y represents the same meaning as Y in formula (rV). ] Perylenetetracarboxylic anhydride represented by the following formula (n
) R-NH! (n) [In formula (II), R represents the same meaning as R in formula (IV). ) has been used to react with the amine shown in
しかし、原料のペリレンテトラ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, perylenetetracarboxylic 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.
［課題を解決するための手段〕
本発明者らは、鋭意検討の結果、下式（ＩＩＩ）〔式（
Ｉ）中、ｘｌ、ｘｔ、 Ｘｉ、ｘ４及びｘＳハ各々独立
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）のペリレンテトラカルボン酸無水物
と式（ＩＩ）のアミンを反応すると高い収率で式（ｒＶ
）のペリレン色素が得られることを見出し、本発明に到
達した。[Means for Solving the Problems] As a result of intensive study, the present inventors have determined that the following formula (III) [Formula (
In I), xl, xt, Xi, x4, and xS each independently represent a hydrogen atom, an alkyl group, or a halogen atom] Using a phenol represented by the following as a solvent, quinoline, isoquinoline, pyridine, monoalkylpyridine, dialkylpyridine , or in the presence or absence of trialkylpyridine, the perylenetetracarboxylic anhydride of formula (I) and the amine of formula (II) are reacted to form the formula (rV
) was found to be able to be obtained, and the present invention was achieved.
式（Ｉ）中、Ｙで示される置換基の具体例としては、Ｉ
ｆ； −ＣＨｚ 、−ＣＪｓ 、−（Ｃ１１ｚ）ｚｃｌ
１３、−Ｃｌｌ（Ｃｌｌ＋Ｌ、−（Ｃ１ｌｚ） ５ｃ１
１ｓ、−ＣＩｌｔＣＩＩ（Ｃｌｌ＊） ｔ、−Ｃｌｌ（
Ｃ１ｈ）ＣＪｓ、（Ｃ１１□）、ＣＨ３、−（ＣＨｚ）
ｓｃｌｈ、−（Ｃ１１□）６ｃＩｌｚ、（Ｃ１１□）？
Ｃ１１，等のアルキル基ｉ −０ＣＨｘ 、−０Ｃ２１
１５、−０（ＣＩ＋□）よＣＨ２、−０（Ｃｌｌ□）ｉ
ｃｌｌｓ 、−０（Ｃ１ｌ□）４ＣＨ２等のアルコキシ
基ｉ Ｃ１，Ｂｒ、 Ｉ 、 Ｆ 、−ＮＩＩＣＨｓ、
−ＮｌｌＣｚｌｌｓ、Ｎ（Ｃｔｌｚ）ｉ、−Ｎ（Ｃ２Ｉ
Ｉｓ）ｔなどが挙げられる。Specific examples of the substituent represented by Y in formula (I) include I
f; -CHz, -CJs, -(C11z)zcl
13, -Cll(Cll+L, -(C1lz) 5c1
1s, -CIltCII(Cll*) t, -Cll(
C1h) CJs, (C11□), CH3, -(CHz)
sclh, -(C11□)6cIlz, (C11□)?
Alkyl group i such as C11, -0CHx, -0C21
15, -0 (CI+□) yo CH2, -0 (Cll□)i
alkoxy group i such as clls, -0(C1l□)4CH2, C1, Br, I, F, -NIICHs,
-NllCzlls, N(Ctlz)i, -N(C2I
Examples include Is)t.
式（ＩＩ）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、γ−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、シクロペ
ンチルアミン、４−ｔｅｒｔ−ブチルアミン、４−ｔｒ
ａｎｓ−アシ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、
ベンチジン、ベンゾオキサゾイルアニリン、アミノアゾ
ヘンゼン、ベンゾチアプリルアニリン、トリジン、ＮＮ
−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、ビフヱ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 (II) include methylamine, ethylamine, propylamine, butylamine, octylamine, γ-methoxyamine, ethoxyethoxyethylamine, β-chloramine, β-methoxycarbonylethylamine. , N, N-
Examples of substituted or unsubstituted cycloalkylamines include dimethylaminoethylamine, cyclopentylamine, 4-tert-butylamine, 4-tr
ans-acylcyclohexylamine, cyclopentylamine, etc. Examples of substituted or unsubstituted arylamines include aniline, toluidine, ethylaniline, methoxycarbonylaniline, nitroaniline, p
-nonylaniline, cetyl aminocarbonylaniline,
Benzidine, benzoxazoylaniline, aminoazohenzene, benzothiaprilaniline, tolidine, NN
Examples of heterocyclic amines include aniline derivatives such as diethylaminoaniline, octyloxycarbonylphenylaniline, benzoxazoylbiphenylamine, and biphenylamine, and fused polycyclic amines such as naphthylamine, alkylnaphthylamine, aminoanthraquinone, and aminoanthracene. Examples include thiopheneamine, benzothiazolamine, nitrothiazoleamine, benzoxazoleamine, pyridineamine, and methylpyridineamine.
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、ρ−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, ρ-chlorophenol, 0-cresol,
m-cresol, p-cresol, ethylphenol,
Examples include butylphenol.
反応条件としては、−飲代（［）で示されるペリレンテ
トラカルボン酸無水物１モルに対して、アミンＭ Ｏ，
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、ｏ、ｏｏｓ〜５モル比を用いるの
が好ましい。The reaction conditions were as follows: amine M O,
The phenol derivative used as a solvent is preferably 7 to 2.0 moles, and the phenol derivative used as a solvent is preferably 5 to 2000 moles. When using quinoline, isoquinoline, pyridine and their derivatives as catalysts, a molar ratio of o, oos to 5 is used. is preferable.
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１１ｎ著となるのは
アリールアミン類、複素環アミン類誘導体のイミドの場
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 arylamine and heterocyclic amine derivatives.
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１９６ ｇ、
実施例２
下式で示される酸無水物１９６ｇ、
２−アミノナフタレン１４３ ｇ、イソキノリン１３０
ｇおよびメタクレゾール１５Ｉ！、の混合物を１５０°
Ｃで４時間加熱攪拌した。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。Example 1 196 g of acid anhydride represented by the following formula, Example 2 196 g of acid anhydride represented by the following formula, 143 g of 2-aminonaphthalene, 130 g of isoquinoline
g and metacresol 15I! , a mixture of
The mixture was heated and stirred at C for 4 hours. After cooling to room temperature, the precipitated crystals were filtered, washed with methanol, and dried.
収！ｔ３ＱＯｇ、此の結晶はＩＲ，ＮＫＲ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は９５％
であることが判った。Revenue! t3QOg, this crystal was identified as the following compound by IR and NKR, and the purity was 95% by liquid chromatography.
It turned out to be.
ｐ−メトキシアニリン１６７ｇ、キノリン１００ｇおよ
び０−クロロフェノール１５ｊ２の混合物を２００°Ｃ
にて６時間加熱攪拌した。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。A mixture of 167 g of p-methoxyaniline, 100 g of quinoline and 15j2 of 0-chlorophenol was heated at 200°C.
The mixture was heated and stirred for 6 hours. After cooling to room temperature, the precipitated crystals were filtered, washed with methanol, and dried.
収量２８０ ｇ、此の結晶は下式の化合物であり、純度
は９６％であった。The yield was 280 g, and the crystals were a compound of the following formula, with a purity of 96%.
実施例３
下記式で示されるカルボン酸無水物２３６ｇ、実施例４
〜１９
下記−飲代に従って、
表１に示すＸ、
Ｒの化合
物を合成した。結果を表１に記す。Example 3 236 g of carboxylic acid anhydride represented by the following formula, Example 4
~19 Compounds X and R shown in Table 1 were synthesized according to the following - drinking costs. The results are shown in Table 1.
２−アミノアントラキノン１６９ｇ、イソキノリン６０
ｇとｐ−クレゾール３０００ ｇの混合物を２００’Ｃ
にて１０時間加熱攪拌した。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-aminoanthraquinone 169g, isoquinoline 60g
A mixture of 3000 g of p-cresol and 3000 g of p-cresol was heated at 200'C.
The mixture was heated and stirred for 10 hours. After cooling to room temperature, the precipitated crystals were filtered, washed with methanol, and dried.
収量３２０ ｇ 、此の結晶は下式の化合物であり、純
度は９４％であった。The yield was 320 g, and the crystals were a compound of the following formula, with a purity of 94%.
Claims (1)
、アルキルアミノ基、水酸基、アルコキシ基、ハロゲン
原子を表す。〕 で示されるペリレンテトラカルボン酸無水物と下式（I
I） 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は各々独立にアルキル基、ハロゲン原子または水
素原子を表す。〕 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は水素原子、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、ハロゲン原
子を表し、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。〕 で示されるペリレン色素の製造方法。[Claims] 1) The following formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula (I), Y is a hydrogen atom, an alkyl group, an amino group, an alkylamino group, a hydroxyl group, Represents an alkoxy group or a halogen atom. ] Perylenetetracarboxylic anhydride represented by the formula (I
I) R-NH_2(II) [In formula (II), R represents a substituted or unsubstituted alkyl group, cyclic alkyl group, aryl group, or heterocycle. ] The 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 Each ^5 independently represents an alkyl group, a halogen atom, or a hydrogen 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 is a hydrogen atom, an alkyl group, an amino group,
It represents an alkylamino group, a hydroxyl group, an alkoxy group, or a halogen atom, and R represents a substituted or unsubstituted alkyl group, a cyclic alkyl group, an aryl group, or a heterocycle. ] A method for producing a perylene dye shown in the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16499888A JPH0216165A (en) | 1988-07-04 | 1988-07-04 | Preparation of perylene coloring matter |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16499888A JPH0216165A (en) | 1988-07-04 | 1988-07-04 | Preparation of perylene coloring matter |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0216165A true JPH0216165A (en) | 1990-01-19 |
| JPH0513991B2 JPH0513991B2 (en) | 1993-02-23 |
Family
ID=15803902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16499888A Granted JPH0216165A (en) | 1988-07-04 | 1988-07-04 | Preparation of perylene coloring matter |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0216165A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007522297A (en) * | 2004-02-11 | 2007-08-09 | ビーエーエスエフ アクチェンゲゼルシャフト | Black perylene pigment |
| CN102453341A (en) * | 2010-11-02 | 2012-05-16 | 上海华元实业总公司 | Method for preparing vat brilliant red RB |
| CN104592228A (en) * | 2014-11-24 | 2015-05-06 | 合肥学院 | Fullerene-perylene functional molecule and preparation method thereof |
-
1988
- 1988-07-04 JP JP16499888A patent/JPH0216165A/en active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007522297A (en) * | 2004-02-11 | 2007-08-09 | ビーエーエスエフ アクチェンゲゼルシャフト | Black perylene pigment |
| CN102453341A (en) * | 2010-11-02 | 2012-05-16 | 上海华元实业总公司 | Method for preparing vat brilliant red RB |
| CN104592228A (en) * | 2014-11-24 | 2015-05-06 | 合肥学院 | Fullerene-perylene functional molecule and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0513991B2 (en) | 1993-02-23 |
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