JPH03294265A - Phthalimide derivative - Google Patents
Phthalimide derivativeInfo
- Publication number
- JPH03294265A JPH03294265A JP9637990A JP9637990A JPH03294265A JP H03294265 A JPH03294265 A JP H03294265A JP 9637990 A JP9637990 A JP 9637990A JP 9637990 A JP9637990 A JP 9637990A JP H03294265 A JPH03294265 A JP H03294265A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- derivative
- parts
- nitro
- 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
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 3
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000565 sulfonamide group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 239000000049 pigment Substances 0.000 abstract description 10
- 150000001448 anilines Chemical class 0.000 abstract description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 7
- MNSGOOCAMMSKGI-UHFFFAOYSA-N N-(hydroxymethyl)phthalimide Chemical class C1=CC=C2C(=O)N(CO)C(=O)C2=C1 MNSGOOCAMMSKGI-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 6
- 238000005859 coupling reaction Methods 0.000 abstract description 5
- 230000008878 coupling Effects 0.000 abstract description 4
- 238000010168 coupling process Methods 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- -1 (substituted) amino Chemical group 0.000 abstract description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract description 2
- 230000018044 dehydration Effects 0.000 abstract description 2
- 238000006297 dehydration reaction Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 1
- JDMRRABYYMMIPA-UHFFFAOYSA-N 2-(hydroxymethyl)-4-methylisoindole-1,3-dione Chemical compound CC1=CC=CC2=C1C(=O)N(CO)C2=O JDMRRABYYMMIPA-UHFFFAOYSA-N 0.000 description 1
- RJBMKFASLAGOHL-UHFFFAOYSA-N 2-(hydroxymethyl)-4-nitroisoindole-1,3-dione Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)N(CO)C(=O)C2=C1 RJBMKFASLAGOHL-UHFFFAOYSA-N 0.000 description 1
- XJCYOJSUFBLZAE-UHFFFAOYSA-N 2-(hydroxymethyl)-5-methylisoindole-1,3-dione Chemical compound CC1=CC=C2C(=O)N(CO)C(=O)C2=C1 XJCYOJSUFBLZAE-UHFFFAOYSA-N 0.000 description 1
- LCUYVSBMPMKCST-UHFFFAOYSA-N 2-(hydroxymethyl)-5-nitroisoindole-1,3-dione Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(CO)C(=O)C2=C1 LCUYVSBMPMKCST-UHFFFAOYSA-N 0.000 description 1
- FPSRUFWSIDRGBT-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]isoindole-1,3-dione Chemical compound C1=CC(N)=CC=C1CN1C(=O)C2=CC=CC=C2C1=O FPSRUFWSIDRGBT-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- WEZAHYDFZNTGKE-UHFFFAOYSA-N 3-ethoxyaniline Chemical compound CCOC1=CC=CC(N)=C1 WEZAHYDFZNTGKE-UHFFFAOYSA-N 0.000 description 1
- AMKPQMFZCBTTAT-UHFFFAOYSA-N 3-ethylaniline Chemical compound CCC1=CC=CC(N)=C1 AMKPQMFZCBTTAT-UHFFFAOYSA-N 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 description 1
- OPGNSNDTPPIYPG-UHFFFAOYSA-N 5-bromo-2-methoxyaniline Chemical compound COC1=CC=C(Br)C=C1N OPGNSNDTPPIYPG-UHFFFAOYSA-N 0.000 description 1
- CGFLAFZHQPHFEL-UHFFFAOYSA-N 5-chloro-2-(hydroxymethyl)isoindole-1,3-dione Chemical compound C1=C(Cl)C=C2C(=O)N(CO)C(=O)C2=C1 CGFLAFZHQPHFEL-UHFFFAOYSA-N 0.000 description 1
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
- ZWUXEXDVHOZEQE-UHFFFAOYSA-N C(O)N1C(C=2C(C1=O)=C(C=CC2)O)=O Chemical compound C(O)N1C(C=2C(C1=O)=C(C=CC2)O)=O ZWUXEXDVHOZEQE-UHFFFAOYSA-N 0.000 description 1
- BSYOECNFLSANNQ-UHFFFAOYSA-N C(O)N1C(C=2C(C1=O)=C(C=CC2)OC)=O Chemical compound C(O)N1C(C=2C(C1=O)=C(C=CC2)OC)=O BSYOECNFLSANNQ-UHFFFAOYSA-N 0.000 description 1
- RNMNEBBWSHXCFT-UHFFFAOYSA-N C(O)N1C(C=2C(C1=O)=C(C=CC2Cl)Cl)=O Chemical compound C(O)N1C(C=2C(C1=O)=C(C=CC2Cl)Cl)=O RNMNEBBWSHXCFT-UHFFFAOYSA-N 0.000 description 1
- KLBTXYDIKYODQG-UHFFFAOYSA-N C(O)N1C(C=2C(C1=O)=CC(=C(C2)Br)Br)=O Chemical compound C(O)N1C(C=2C(C1=O)=CC(=C(C2)Br)Br)=O KLBTXYDIKYODQG-UHFFFAOYSA-N 0.000 description 1
- LUVZJRYVXOZMKA-UHFFFAOYSA-N C(O)N1C(C=2C(C1=O)=CC(=CC2)N)=O Chemical compound C(O)N1C(C=2C(C1=O)=CC(=CC2)N)=O LUVZJRYVXOZMKA-UHFFFAOYSA-N 0.000 description 1
- TWLLPUMZVVGILS-UHFFFAOYSA-N Ethyl 2-aminobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1N TWLLPUMZVVGILS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- CDGNLUSBENXDGG-UHFFFAOYSA-N meta-Cresidine Chemical compound COC1=CC=C(N)C(C)=C1 CDGNLUSBENXDGG-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MPXAYYWSDIKNTP-UHFFFAOYSA-N n-(2-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC=C1N MPXAYYWSDIKNTP-UHFFFAOYSA-N 0.000 description 1
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-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
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は新規なフタルイミド誘導体に関し、更に詳しく
は、染料、顔料等の原料として有用なフタルイミド誘導
体に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a novel phthalimide derivative, and more particularly to a phthalimide derivative useful as a raw material for dyes, pigments, and the like.
（従来の技術及びその問題点）
従来、染料、顔料等の原料として多種多様なアニリン誘
導体が知られている。例えば、顔料用の中間体であるア
ニリン誘導体としては、得られる顔料の耐候性、耐溶剤
製等が高（なるものが求められているが、現在十分に満
足出来るアニリン誘導体は知られていない。(Prior Art and its Problems) A wide variety of aniline derivatives have been known as raw materials for dyes, pigments, and the like. For example, aniline derivatives that are intermediates for pigments are required to provide pigments with high weather resistance, solvent resistance, etc., but currently no aniline derivatives that are fully satisfactory are known.
従って、本発明の目的は、染料、顔料等の原料として有
用な中間体を提供することである。Therefore, an object of the present invention is to provide an intermediate useful as a raw material for dyes, pigments, and the like.
（問題点を解決する為の手段） 上記目的は以下の本発明によって達成される。(Means for solving problems) The above objects are achieved by the present invention as described below.
即ち、本発明は、−船底（Ｉ）
１
＋＋ １
（式中のＸは水素原子、１個以上のハロゲン原子、低級
アルキル基、低級アルコキシ基、ニトロ基、ハロゲン原
子、アミノ基、置換アミノ基、アルコキシカルボニル基
等の置換基を表し、Ｙは水素原子、１個以上のハロゲン
原子、低級アルキル基、低級アルコキシ基、ニトロ基、
アルコキシカルボニル基、カルボキシル基、スルホンア
ミド基、スルホン酸基等の置換基を表す。）で表される
フタルイミド誘導体である。That is, the present invention provides - bottom (I) 1 ++ 1 (wherein X is a hydrogen atom, one or more halogen atoms, a lower alkyl group, a lower alkoxy group, a nitro group, a halogen atom, an amino group, a substituted amino group) , represents a substituent such as an alkoxycarbonyl group, Y is a hydrogen atom, one or more halogen atoms, a lower alkyl group, a lower alkoxy group, a nitro group,
Represents a substituent such as an alkoxycarbonyl group, carboxyl group, sulfonamide group, or sulfonic acid group. ) is a phthalimide derivative represented by
（作 用）
一般式（Ｉ）のフタルイミド誘導体をジアゾ化し、適当
なカップリング成分とカップリングさせると、耐候性や
耐溶剤性等に優れた顔料が得られる。又、染料の中間体
としても有用である。(Function) When the phthalimide derivative of general formula (I) is diazotized and coupled with a suitable coupling component, a pigment with excellent weather resistance, solvent resistance, etc. can be obtained. It is also useful as an intermediate for dyes.
（好ましい実施態様）
次に好ましい実施態様を挙げて本発明を更に詳しく説明
する。(Preferred Embodiments) Next, the present invention will be described in more detail by citing preferred embodiments.
本発明のフタルイミド誘導体は、アニリン誘導体とＮ−
ヒドロキシメチルフタルイミド誘導体とを、例えば、濃
硫酸中で脱水縮合することによって得られる。The phthalimide derivative of the present invention is an aniline derivative and an N-
It can be obtained, for example, by dehydration condensation with a hydroxymethylphthalimide derivative in concentrated sulfuric acid.
原料として使用出来るアニリン誘導体としては、
アニリン、
ｏ、ｍ又はｐ−クロルアニリン、
ｏ、ｍ又はｐ−メチルアニリン、
ｏ、ｍ又はｐ−エチルアニリン、
ｏ、ｍ又はｐ−メトキシアニリン、
ｏ、ｍ又はｐ−エトキシアニリン、
ｏ、ｍ又はｐ−ニトロアニリン、
ｏ、ｍ又はｐ−アミノアセトアニリド、２−メチル−４
−クロルアニリン、
２−メチル−５−クロルアニリン、
２．６−キシリジン、
２．４−キシリジン、
２．５−キシリジン、
２−メトキシ−５−クロルアニリン、
２−メトキシ−５−ブロモアニリン、
２−メチル−４−メトキシアニリン、
２．５−ジメトキシアニリン、
２．４−ジメトキシアニリン、
２−メトキシ−５−メチルアニリン、
アントラニル酸メチルエステル、
アントラニル酸エチルエステル等が挙げられる。Aniline derivatives that can be used as raw materials include: aniline, o, m or p-chloroaniline, o, m or p-methylaniline, o, m or p-ethylaniline, o, m or p-methoxyaniline, o, m or p-ethoxyaniline, o, m or p-nitroaniline, o, m or p-aminoacetanilide, 2-methyl-4
-Chloraniline, 2-methyl-5-chloroaniline, 2.6-xylidine, 2.4-xylidine, 2.5-xylidine, 2-methoxy-5-chloroaniline, 2-methoxy-5-bromoaniline, 2 -Methyl-4-methoxyaniline, 2.5-dimethoxyaniline, 2.4-dimethoxyaniline, 2-methoxy-5-methylaniline, anthranilic acid methyl ester, anthranilic acid ethyl ester, and the like.
又、Ｎ−ヒドロキシメチルフタルイミド類としては、
Ｎ−ヒドロキシメチルフタルイミド、
Ｎ−ヒドロキシメチル−４−二トロフタルイミド、
Ｎ−ヒドロキシメチル−３−二トロフタルイミド、
Ｎ−ヒドロキシメチル−３−ヒドロキシフタルイミド、
Ｎ−ヒドロキシメチル−３−クロルフタルイミド、
Ｎ−ヒドロキシメチル−４−クロルフタルイミド、
Ｎ−ヒドロキシメチル−３，６−ジクロルフタルイミド
、
Ｎ−ヒドロキシメチル−３，４，５６−チトラクロルフ
タルイミド、
Ｎ−ヒドロキシメチル−３，４，５，６−チトラブロモ
フタルイミド、
Ｎ−ヒドロキシメチル−４−アミノフタルイミド、
Ｎ−ヒドロキシメチル−３−メトキシフタルイミド、
Ｎ−ヒドロキシメチル−３−メチルフタルイミド、
Ｎ−ヒドロキシメチル−４−メチルフタルイミド、
Ｎ−ヒドロキシメチル−４，５−ジブロモフタルイミド
等が挙げられる。In addition, as N-hydroxymethylphthalimides, N-hydroxymethylphthalimide, N-hydroxymethyl-4-nitrophthalimide, N-hydroxymethyl-3-nitrophthalimide, N-hydroxymethyl-3-hydroxyphthalimide, N-hydroxymethylphthalimide -Hydroxymethyl-3-chlorophthalimide, N-hydroxymethyl-4-chlorophthalimide, N-hydroxymethyl-3,6-dichlorophthalimide, N-hydroxymethyl-3,4,56-titrachlorophthalimide, N-hydroxy Methyl-3,4,5,6-titrabromophthalimide, N-hydroxymethyl-4-aminophthalimide, N-hydroxymethyl-3-methoxyphthalimide, N-hydroxymethyl-3-methylphthalimide, N-hydroxymethyl-4 -methylphthalimide, N-hydroxymethyl-4,5-dibromophthalimide, and the like.
前記アニリン誘導体と上記Ｎ−ヒドロキシメチルフタル
イミド類との反応は、特に限定されないが、両者をほぼ
等モル比で８０〜１００％の濃硫酸中で一１０〜１００
℃程度の温度で数時間〜数十時間反応させ、その後水中
又は氷水中に注入し、析出した沈澱を濾過することによ
って本発明の目的物が得られる。The reaction between the aniline derivative and the N-hydroxymethylphthalimide is not particularly limited, but the two are reacted in a substantially equimolar ratio of 110 to 100% in concentrated sulfuric acid of 80 to 100%.
The object of the present invention can be obtained by reacting at a temperature of about 0.degree. C. for several hours to several tens of hours, then pouring into water or ice water, and filtering the precipitate.
（実施例）
次に実施例を挙げて本発明を更に具体的に説明する。尚
、文中部又は％とあるのは特に断りの無い限り重量基準
である。(Example) Next, the present invention will be described in more detail with reference to Examples. It should be noted that unless otherwise specified, the terms in the text or % are based on weight.
実施例１
アニリン１１．０部を８５％硫酸１１０部中に１５〜２
０℃で撹拌しながら加えて溶解させ、同温度でＮ−ヒド
ロキシメチルフタルイミド１６．８部を加えて２０〜２
５℃で２４時間撹拌後、氷水１０００部中へ５℃以下で
少量づつ加え、析出した結晶を濾過し、中性まで水洗し
て８０℃で乾燥すると、収率８０％で淡黄色のｐ−フタ
ルイミドメチルアニリン（ｍｐ１５５〜１５７℃）が得
られた。Example 1 11.0 parts of aniline in 110 parts of 85% sulfuric acid at 15-2
Add and dissolve at 0°C with stirring, and at the same temperature add 16.8 parts of N-hydroxymethylphthalimide to make 20-20%
After stirring at 5°C for 24 hours, the crystals were added little by little to 1000 parts of ice water at 5°C or below, the precipitated crystals were filtered, washed with water until neutral, and dried at 80°C. Phthalimidomethylaniline (mp 155-157°C) was obtained.
上記のｐ−フタルイミドメチルアニリン１２．６部を１
２５部の氷水及び６３部の２Ｎ塩酸に一部溶解分散し、
２５部の２Ｎ亜硝酸ソーダ溶液でジアゾ化する。12.6 parts of the above p-phthalimidomethylaniline
Partially dissolved and dispersed in 25 parts of ice water and 63 parts of 2N hydrochloric acid,
Diazotize with 25 parts of 2N sodium nitrite solution.
一方、１６．５部の５− （２′、３′−オキシナフト
イルアミノ）−ベンツイミダシロンを３００部の水及び
６５部の２Ｎ苛性ソーダ溶液に溶解し、これに先のジア
ゾ液を滴下してカップリング反応を行う。その後１時間
９５℃に加熱処理し、濾過、水洗及び乾燥して下記構造
の赤色顔料２７．０部が得られた。Meanwhile, 16.5 parts of 5-(2',3'-oxynaphthoylamino)-benzimidacylone was dissolved in 300 parts of water and 65 parts of 2N caustic soda solution, and the above diazo solution was added dropwise to this. to perform the coupling reaction. Thereafter, the mixture was heated at 95° C. for 1 hour, filtered, washed with water, and dried to obtain 27.0 parts of a red pigment having the following structure.
実施例２
ｏ−）ルビ９２フ４２部を９５％硫酸１５０部中に２０
〜２５℃で撹拌しながら加えて溶解させ、同温度でＮ−
ヒドロキシメチル−３，４５，６−テトラクロルフタル
イミド２２部を加えて２０〜２５℃で４８時間撹拌後、
氷水１５００部中に１０℃以下で少量づつ加え、析出し
た結晶を濾過し、中性まで水洗して８０℃で乾燥すると
、収率９５％で淡黄色の４− （３，４，５，６−チト
ラクロルフタルイミドメチル）−２−メチルアニリン（
ｍ ｐ ２２５〜２２６℃）が得られた。Example 2 o-) 42 parts of Ruby 92F in 150 parts of 95% sulfuric acid at 20%
Add and dissolve with stirring at ~25°C, and add N- at the same temperature.
After adding 22 parts of hydroxymethyl-3,45,6-tetrachlorophthalimide and stirring at 20 to 25°C for 48 hours,
The crystals were added little by little to 1,500 parts of ice water at 10°C or less, filtered, washed with water until neutral, and dried at 80°C to give pale yellow 4-(3,4,5,6 -titrachlorphthalimidomethyl)-2-methylaniline (
m p 225-226°C) was obtained.
上記の４− （３，４，５，６−チトラクロルフタルイ
ミドメチル）−２−メチルアニリン４．０部を塩酸中で
常法によりジアゾ化し、ジアゾニウム塩溶液を得る。こ
のジアゾ液をアセトアセト−２５−ジメトキシ−４−ク
ロルアニリド２．８部の酢酸酸性懸濁液に滴下してカッ
プリングすることにより、下記構造を有する鮮黄色のア
ゾ顔料６．５部を得た。4.0 parts of the above 4-(3,4,5,6-titrachlorophthalimidomethyl)-2-methylaniline is diazotized in hydrochloric acid by a conventional method to obtain a diazonium salt solution. This diazo liquid was added dropwise to an acetic acid acidic suspension of 2.8 parts of acetoaceto-25-dimethoxy-4-chloroanilide and coupled to obtain 6.5 parts of a bright yellow azo pigment having the following structure. .
実施例３〜２９
実施例１又は２と同様にして下記第１表の原料を使用し
、−数式（Ｉ）のフタルイミド誘導体を得た。Examples 3 to 29 Phthalimide derivatives of formula (I) were obtained in the same manner as in Example 1 or 2 using the raw materials shown in Table 1 below.
第
表
＊分解
（効 果）
以上の如き本発明によれば、−数式（Ｉ）のフタルイミ
ド誘導体をジアゾ化し、適当なカップリング成分とカッ
プリングさせると、耐候性や耐溶剤性等に優れた顔料が
得られる。又、染料の中間体としても有用である。Table *Decomposition (Effects) According to the present invention as described above, when the phthalimide derivative of the formula (I) is diazotized and coupled with an appropriate coupling component, it has excellent weather resistance, solvent resistance, etc. A pigment is obtained. It is also useful as an intermediate for dyes.
他１名1 other person
Claims (1)
アルキル基、低級アルコキシ基、ニトロ基、ハロゲン原
子、アミノ基、置換アミノ基、アルコキシカルボニル基
等の置換基を表し、Ｙは水素原子、１個以上のハロゲン
原子、低級アルキル基、低級アルコキシ基、ニトロ基、
アルコキシカルボニル基、カルボキシル基、スルホンア
ミド基、スルホン酸基等の置換基を表す。）で表される
フタルイミド誘導体。[Claims] General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (X in the formula is a hydrogen atom, one or more halogen atoms, a lower alkyl group, a lower alkoxy group, a nitro group , represents a substituent such as a halogen atom, an amino group, a substituted amino group, an alkoxycarbonyl group, and Y is a hydrogen atom, one or more halogen atoms, a lower alkyl group, a lower alkoxy group, a nitro group,
Represents a substituent such as an alkoxycarbonyl group, carboxyl group, sulfonamide group, or sulfonic acid group. ) A phthalimide derivative represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2096379A JP2641107B2 (en) | 1990-04-13 | 1990-04-13 | Method for producing azo pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2096379A JP2641107B2 (en) | 1990-04-13 | 1990-04-13 | Method for producing azo pigment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03294265A true JPH03294265A (en) | 1991-12-25 |
| JP2641107B2 JP2641107B2 (en) | 1997-08-13 |
Family
ID=14163331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2096379A Expired - Lifetime JP2641107B2 (en) | 1990-04-13 | 1990-04-13 | Method for producing azo pigment |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2641107B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07331105A (en) * | 1994-06-06 | 1995-12-19 | Dainichiseika Color & Chem Mfg Co Ltd | Preparation of azo dye |
| JP2008095007A (en) * | 2006-10-13 | 2008-04-24 | Dainichiseika Color & Chem Mfg Co Ltd | Pigment dispersant, pigment composition, pigment coloring agent and coating liquid for color filter |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101721069B1 (en) * | 2015-01-05 | 2017-03-29 | 주식회사 유엔아이 | Pigment Derivatives or Pigment Dispersion Composition Comprising Thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55142751A (en) * | 1979-04-18 | 1980-11-07 | Mitsubishi Rayon Co | Production of easily raisable weft knitted fabric |
| JPS55147251A (en) * | 1980-03-11 | 1980-11-17 | Wako Pure Chem Ind Ltd | Preparation of novel azobenzylamine compound (1) |
-
1990
- 1990-04-13 JP JP2096379A patent/JP2641107B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55142751A (en) * | 1979-04-18 | 1980-11-07 | Mitsubishi Rayon Co | Production of easily raisable weft knitted fabric |
| JPS55147251A (en) * | 1980-03-11 | 1980-11-17 | Wako Pure Chem Ind Ltd | Preparation of novel azobenzylamine compound (1) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07331105A (en) * | 1994-06-06 | 1995-12-19 | Dainichiseika Color & Chem Mfg Co Ltd | Preparation of azo dye |
| JP2008095007A (en) * | 2006-10-13 | 2008-04-24 | Dainichiseika Color & Chem Mfg Co Ltd | Pigment dispersant, pigment composition, pigment coloring agent and coating liquid for color filter |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2641107B2 (en) | 1997-08-13 |
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