KR830001354A - Method for producing basic dye - Google Patents

Method for producing basic dye Download PDF

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KR830001354A
KR830001354A KR1019790004065A KR790004065A KR830001354A KR 830001354 A KR830001354 A KR 830001354A KR 1019790004065 A KR1019790004065 A KR 1019790004065A KR 790004065 A KR790004065 A KR 790004065A KR 830001354 A KR830001354 A KR 830001354A
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structural formula
alkyl
phenyl
carbon atoms
hydrogen
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KR1019790004065A
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KR830001369B1 (en
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하인쯔 헤르만 칼
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귄터 피터스, 하인쯔-게르트 뮐러
바이엘 아크티엔 게젤샤프트
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00Diaryl- or thriarylmethane dyes
    • C09B11/04Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10Amino derivatives of triarylmethanes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00Diaryl- or thriarylmethane dyes
    • C09B11/04Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/26Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
  • Coloring (AREA)

Abstract

내용 없음No content

Description

염기성 염료의 제조방법Method for producing basic dye

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음This content is subject to disclosure, so the full text is not included.

Claims (3)

일반 구조식 III의 화합물을 할로겐 또는 시아노로 치환된 벤조퀴논이나 니트로로 치환된 페난트렌퀴논 촉매 존재시 및 디나이트로젠 모노옥사이드를 제외한 나이트로젠 옥사이드 또는 이 반응 상태하에서 나이트로젠 옥사이드를 생성하는 물질 촉매 존재시에 산소로 산회시킴으로써 일반 구조식 I의 염기성 염료를 제조하는 방법.In the presence of a benzoquinone substituted with a halogen or cyano or a phenanthrenequinone catalyst substituted with a nitro and a nitrogen oxide excluding dinitrogen monooxide or a material catalyst that generates nitrogen oxide under this reaction state A method of preparing a basic dye of general structural formula I by acidifying it with oxygen. 상기 구조식중 A와 B는 각기 별개로 이종 지방족 잔기 또는 일반 구조식 II잔기를 나타낸다.In the above structural formula, A and B each independently represent a heterologous aliphatic residue or a general structural formula II residue. 또한 상기 구조식중 Y는 수소 또는 비이온성 치환체를 나타내고 n는 1-4이며 R1및 R2는 수소 또는 알킬, 아릴 또는 비이온성이나 산성 그룹에 의해 임의치환된 아랄킬이며 R1, R2가 함께 또는 0-위치의 Ar과 같이 복소환을 형성한다.In addition, in the above structural formula, Y represents hydrogen or a nonionic substituent, n is 1-4, R 1 and R 2 are hydrogen or aralkyl optionally substituted by an alkyl, aryl or nonionic or acidic group, and R 1 and R 2 are Together or form a heterocycle such as Ar at the 0-position. D는 수소, 알킬, 중성 또는 산성그룹으로 임의 치환된 아릴 또는 이종 방향족 잔기이고 X-는 음이온을 나타낸다.D is hydrogen, alkyl, aryl or heteroaromatic moiety optionally substituted with a neutral or acidic group, and X - represents an anion. 상기 구조식중 A, B 및 D는 상기에 기술된 바와 같다.In the above structural formula, A, B and D are as described above. 일반구조식 X의 화합물을 나이트로젠모노옥사이드, 나이트로젠 디옥사이드, 소디움 나이트라이트 또는 철-III 나이트레이트 촉매 존재시 산소로 산화시킴으로써 구조식 IV의 화합물을 제조함을 특징으로 하는 특허청구범위 1에 따르는 방법.A method according to claim 1, characterized in that the compound of formula IV is prepared by oxidizing the compound of general formula X with oxygen in the presence of a nitrogen monooxide, nitrogen dioxide, sodium nitrite or iron-III nitrate catalyst. 상기 구조식중 R3및 R5는 서로 별개의 수소, C1-~C4-알킬, 탄소수 2 또는 3개의 하이드록시 알킬, 시아노에틸, 탄소수 총 3-5개의 알콕시알킬, 탄소수 총 3-8개의 알콕시카보닐알킬, 탄소수 총 3-8개의 알킬카보닐옥시알킬, C1-~C4-할로게노알킬, 탄소수 2-4개의 설포알킬, 사이클로헥실, 벤질, 페닐페네틸, 할로겐 또는 C1-C4-알킬이나-알콕시로 치환된 페닐 또는 설포벤질을 나타내고 R4및 R6는 C1-C4-알킬, 탄소수 2 또는 3개의 하이드록시-알킬, 시아노에틸, C1-~C4-할로게노알킬, 탄소수 총 3-5개의 알콕시알킬, 탄소수 총 3-8개의 알콕시카보닐알킬, 탄소수 총 3-8개의 알킬카보닐옥시알킬 또는 벤질을 나타내거나 R30R4및/또는 R5와 R6는 함께 피롤리딘, 피페리딘, 모르폴린 또는C1-C4알킬로 임의 치환된 피페라진 환을 형성하고 R3, R4, R5및/또는 R6는 0-위치의 페닐환과 함께 테트라하이드로 퀴놀린, 인돌린, 줄로리딘, 페노모르폴린, 테트라하이드로 퀴녹살린 또는 C1-C4-알킬, 페닐 또는 벤질로 임의 치환된 카바졸 환을 형성한다.In the above structural formula, R 3 and R 5 are different from each other hydrogen, C 1 -~ C 4 -alkyl, hydroxyalkyl having 2 or 3 carbon atoms, cyanoethyl, alkoxyalkyl having a total of 3-5 carbon atoms, and 3-8 carbon atoms in total Alkoxycarbonylalkyl, alkylcarbonyloxyalkyl having a total of 3-8 carbon atoms, C 1 -to C4-halogenoalkyl, sulfoalkyl having 2-4 carbon atoms, cyclohexyl, benzyl, phenylphenethyl, halogen or C 1- C 4 -alkyl or alkoxy substituted phenyl or sulfobenzyl, and R 4 and R 6 are C 1 -C 4 -alkyl, hydroxy-alkyl having 2 or 3 carbon atoms, cyanoethyl, C 1 -~ C 4 -Halogenoalkyl, a total of 3 to 5 carbon atoms alkoxyalkyl, a total of 3 to 8 carbon atoms alkoxycarbonylalkyl, a total of 3 to 8 carbon atoms alkylcarbonyloxyalkyl or benzyl, or R 30 R 4 and/or R 5 And R 6 together form a piperazine ring optionally substituted with pyrrolidine, piperidine, morpholine or C 1 -C 4 alkyl, and R 3 , R 4 , R 5 and/or R 6 are at the 0-position Together with the phenyl ring, tetrahydroquinoline, indoline, julolidine, phenomorpholine, tetrahydroquinoxaline or C 1 -C 4 -alkyl, phenyl or benzyl optionally substituted carbazole ring is formed. R7및 R8는 수소, C1-~C4-알킬, C1-~C4-알콕시 또는 할로겐을 나타내고,R 7 and R 8 represent hydrogen, C 1 -~C 4 -alkyl, C 1 -~C 4 -alkoxy or halogen, n은 1-4의 정수를 나타내며,n represents an integer of 1-4, E는 페닐이거나 할로겐, C1-~C4-알킬, C1-~C4-알콕시, 니트로, 카복실 그룹 또는 설폰산 그룹으로 모노 치환되거나 디치환된 페닐 또는 나프틸이거나 일반 구조식 V의 복소환 잔기를 나타낸다.E is phenyl or halogen, C 1 -~C 4 -alkyl, C 1 -~C 4 -alkoxy, nitro, phenyl or naphthyl mono-substituted or disubstituted with a sulfonic acid group, or a heterocycle of the general formula V Represents a residue. 상기 구조식중 R9은 수소 C1-C4-알킬, 페닐, 카복실산 C1-또는 C2-알킬 에스테르, C1-C4-알킬 또는 C1-C4알콕시로 임의 N-치환된 카복실산 아미드를 나타낸다.In the above structural formula, R 9 is a carboxylic acid amide optionally N-substituted with hydrogen C 1 -C 4 -alkyl, phenyl, carboxylic acid C 1 -or C 2 -alkyl ester, C 1 -C 4 -alkyl or C 1 -C 4 alkoxy Represents. 또는 E가 일반 구조식 VI 이나 VII의 잔기를 나타낸다.Or E represents a residue of general structural formula VI or VII. 상기 구조식중 n, R3, R4및 R7은 전술된 바와 같다. 또는 E가 일반 구조식 VIII이나 IX의 잔기를 나타낸다.In the above structural formula, n, R 3 , R 4 and R 7 are as described above. Or E represents a residue of general structural formula VIII or IX. 상기 구조식중 R10은 수소, C1-C4-알킬 또는 할로겐 특히 염소 또는 취소를 나타내고, n, R3, R4, R5R6, R7및 R8는 상기에 상술된 바와 같으며 X도 전술된 바와 같다.In the above structural formula, R 10 represents hydrogen, C 1 -C 4 -alkyl or halogen, especially chlorine or cancel, and n, R 3 , R 4 , R 5 R 6 , R 7 and R 8 are as described above, and X is also as described above. 상기 구조식중 n 및 R3~R8는 전술된 바와 같고 F는 E와 같거나 일반 구조식 XI 또는 XII의 잔기이다.In the above structural formula, n and R 3 to R 8 are as described above, and F is the same as E or a residue of general structural formula XI or XII. 상기 구조식중 n, R3-R8및 R10은 전술된 바와 같다.In the above structural formula, n, R 3 -R 8 and R 10 are as described above. 특허청구범위 2에서의 구조식 IV화합물이 상ㅇ,ㅇ하는 트리아릴메탄 유도체를 테트라클로로-또는 테트라브로모-1,4-벤조퀴논 촉매 및 나이트로젠 모노옥사이드 및/또는 나이트로젠 디옥사이드 촉매 존재시 산소로 산화시킴으로써 제조됨을 특징으로 하는 특허청구 범위 1에 따르는 방법.Triarylmethane derivatives having different structural formula IV compounds in claim 2 are used in the presence of tetrachloro- or tetrabromo-1,4-benzoquinone catalysts and nitrogen monooxide and/or nitrogen dioxide catalysts. A method according to claim 1, characterized in that it is produced by oxidation with. 일반구조식 IV 중 R3및R5는 수소, 메틸, 에틸하이드록시에틸, 프로필 또는 부틸을 나타내고 R4및 R6는 메틸, 에틸, 설포벤질 또는 설포에틸을 나타내며 R7및R8는 수소, 메틸, 메톡시 또는 염소를 나타낸다. E는 페닐 이거나 염소, 메톡시 또는 설폰산 그룹으로 치환된 페닐, P-디메틸 아미노페닐, P-디에틸 아미노페닐, P-비스하이드록시아텔아미노페닐 또는 일반 구조식 V의 잔기를 나타낸다.In General Formula IV, R 3 and R 5 represent hydrogen, methyl, ethylhydroxyethyl, propyl or butyl, R 4 and R 6 represent methyl, ethyl, sulfobenzyl or sulfoethyl, and R 7 and R 8 represent hydrogen, methyl , Methoxy or chlorine. E represents phenyl or phenyl substituted with a chlorine, methoxy or sulfonic acid group, P-dimethyl aminophenyl, P-diethyl aminophenyl, P-bishydroxyatelaminophenyl or a residue of general structural formula V. 상기 구조식중 R3'는 수소, 메틸 또는 페닐을 나타내고 R9'은 메틸 또는 페닐을 나타내며, n 및 X-는 특허청구 범위 2에서 기술된 바와 같다.In the above structural formula, R 3 ′ represents hydrogen, methyl or phenyl, R 9 ′ represents methyl or phenyl, and n and X - are as described in Claim 2. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: It is disclosed according to the contents of the initial application.
KR1019790004065A 1979-11-20 1979-11-20 How to prepare basic dye KR830001369B1 (en)

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