KR930010503B1 - New alpha-tape quinacridone derivatives and preparation thereof - Google Patents

New alpha-tape quinacridone derivatives and preparation thereof Download PDF

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KR930010503B1
KR930010503B1 KR1019900015291A KR900015291A KR930010503B1 KR 930010503 B1 KR930010503 B1 KR 930010503B1 KR 1019900015291 A KR1019900015291 A KR 1019900015291A KR 900015291 A KR900015291 A KR 900015291A KR 930010503 B1 KR930010503 B1 KR 930010503B1
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general formula
formula
derivative
alpha
quinacridone
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KR920006447A (en
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박상우
유경호
강용구
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한국과학기술연구원
박원희
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Priority to CH193/91A priority patent/CH682077A5/de
Priority to JP3089276A priority patent/JPH0647590B2/en
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0025—Crystal modifications; Special X-ray patterns
    • C09B67/0027—Crystal modifications; Special X-ray patterns of quinacridones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B48/00—Quinacridones

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Abstract

Quinacridone derivatives of formula (I) are prepd. by (a) reacting diethyl 1,4-dicyclohexadione-2,5-dicarboxylate with aromatic amine derivatives such as 5-aminoindane, 3,4-(methylenedioxy) aniline, 2-aminofluorene, 3- amino-9-ethylcarbazole in the presence of trifluoroacetic acid to obtain diethyl 2,5-dianilino-3,6-dihydroterephthalate (II), (b) reacting (II) in a mixed solvent of biphenyl and diphenylether at 250-270 deg.C for 1 hr to obtain 6,13-dihydroquinacridone (II), and (c) oxidn. of (III) with m-nitrobenzene sulfonic acid sodium salt in ethanol, water and NaOH solution. In formula (I), A= cyclopentyl, methylenedioxy, indanyl or N-ethyl indolyl.

Description

새로운 알파형 퀴나크리돈계 유도체 및 그 제조방법New alpha-quinacridone derivatives and preparation method thereof

본 발명은 일반식(I)로 표시되는 새로운 알파형 퀴나크리돈(Quincaridone)계 안료 유도체 및 그 제조방법에 관한 것이다.The present invention relates to a novel alpha-type quinacridone pigment derivative represented by formula (I) and a method for producing the same.

Figure kpo00001
Figure kpo00001

상기 일반식(I)에서 A는 하나 또는 두개의 고리를 가진 시클로펜틸, 메틸렌디옥시, 인다닐 또는 N-메틸 인돌릴과 시클로알킬 및 아릴기를 나타낸다.In general formula (I), A represents cyclopentyl, methylenedioxy, indanyl or N-methyl indolyl and a cycloalkyl and aryl group having one or two rings.

퀴나크리돈의 제조방법은 미국특허 2,821,541, 독일특허 1,253,705, 미국특허 3,287,457 및 2,821,529등에 잘 나타나 있으며, 대표적인 방법은 다음과 같다.Methods for preparing quinacridone are well described in US Patent 2,821,541, German Patent 1,253,705, US Patent 3,287,457, and 2,821,529, and the like.

Figure kpo00002
Figure kpo00002

Figure kpo00003
Figure kpo00003

Figure kpo00004
Figure kpo00004

즉, 구조식(II)의 디에틸 1,4-디시크로헥산디온-2,5-디카르복실레이트를 아닐린과 반응시켜 구조식(III)의 디에틸 2,5-디아닐리노-3,6-디히드로테레프탈레이트를 제조하고, 이 구조식(III)의 화합물을 고리화 반응으로 구조식(IV)의 6,13-디히드로 퀴나크리돈을 제조한 후 메타-니트로벤젠술폰산 나트륨염을 사용하여 구조식(V)의 알파형 퀴나크리돈을 제조한다.That is, diethyl 1,4-dicyclohexanedione-2,5-dicarboxylate of formula (II) is reacted with aniline to diethyl 2,5-dianilin-3,6- of formula (III) Dihydroterephthalate was prepared, and 6,13-dihydroquinacridone of formula (IV) was prepared by cyclization of the compound of formula (III), followed by the use of sodium meta-nitrobenzenesulfonic acid sodium salt Alpha type quinacridone of V) is prepared.

이러한 구조식(V)의 알파형 퀴나크리돈을 미국특허 2,844,485 및 2,844,581에서 나타난 것처럼 크실렌이나 디메틸포름아미드 등의 용매를 사용하여 구조식(V)의 베타형 및 감마형 퀴나크리돈으로 전환하고 있다.The alpha type quinacridone of formula (V) is converted to beta and gamma quinacridones of formula (V) using a solvent such as xylene or dimethylformamide as shown in US Pat. Nos. 2,844,485 and 2,844,581.

구조식(V)의 퀴나크리돈은 알파, 베타, 감마 및 델타형의 4개의 다른 결정상태로 존재할 수 있으며, 이들형태는 X-선 회절법에 의해 특징화된다. 이와 같은 구조식(V)의 퀴나크리돈의 벤젠핵치환유도체들은 염소, 메틸기 등이 알려져 있으나, 고리화합물이 첨가된 유도체들은 극소수, 예컨대 벤젠 등이 알려져 있는데, 상업적으로는 바람직하지 못한 것으로 생각된다. 공지화합물에서의 R은 염소, 메틸기 등의 치환기들이나 벤젠등의 고리화합물을 나타낸다.Quinacridone of formula (V) may exist in four different crystalline states, alpha, beta, gamma and delta forms, and these forms are characterized by X-ray diffraction methods. Although the benzene nucleus derivatives of the quinacridone of the structural formula (V) are known chlorine and methyl groups, very few derivatives to which the cyclic compounds are added are known, such as benzene, but are not considered commercially desirable. R in a known compound represents substituents, such as chlorine and a methyl group, and cyclic compounds, such as benzene.

본 발명은 새로운 색상과 입자상의 신규 퀴나크리돈계 안료를 개발하기 위하여 하나 또는 두개의 고리가 증가된 일반식(I)의 새로운 알파형 퀴나크리돈계 유도체를 제조하는 것을 특징으로 한다.The present invention is characterized by the preparation of new alpha-type quinacridone derivatives of general formula (I) with one or two rings increased in order to develop new quinacridone pigments in new colors and particles.

여기서, 시클로펜틸과 메틸렌디옥시 등의 고리가 첨가된 일반식(I)의 퀴나크리돈계 유도체들은 적색계열의 화합물로서, 이중에서 특히 시클로펜틸의 경우 매우 우수한 색상 및 선명도를 가지는 것으로 나타났다.Herein, the quinacridone derivatives of the general formula (I) to which a ring such as cyclopentyl and methylenedioxy are added are red compounds, and particularly, cyclopentyl has a very good color and sharpness.

본 발명의 반응개요를 살펴보면 다음과 같다.Looking at the reaction overview of the present invention.

[제1공정][Step 1]

Figure kpo00005
Figure kpo00005

Figure kpo00006
Figure kpo00006

[제2공정][Step 2]

Figure kpo00007
Figure kpo00007

[제3공정][Step 3]

Figure kpo00008
Figure kpo00008

각 반응을 반응공정별로 상세히 살펴보면, 제1공정에서 일반식(II)의 디에틸, 1,4-디시클로헥산디온-2,5-디카르복실레이트를 질소기류하에서 톨루엔이나 크실렌을 용매로 사용하고 트리플루오로 아세트산을 촉매로 사용하여 이란식(III)의 방향족아민 유도체와 반응시켜 일반식(VI)의 디에틸 2,5-디아닐리노-3,6-디히드로테레프탈레이티트 유도체를 제조한다. 이때 사용한 일반식(III)의 방향족 아민은 5-아미노인단, 3,4-(메틸렌디옥시)아닐린, 2-아미노플루오렌 또는 3-아미노-9-에틸카바졸이며, 일반식(VI)에서 A는 시클로펜틸, 메틸렌디옥시, 인다닐 또는 N-에틸 인돌릴과 시크로알킬 및 아릴기를 나타낸다.Looking at each reaction in detail by the reaction step, toluene or xylene as a solvent in the first step using diethyl, 1,4-dicyclohexanedione-2,5-dicarboxylate of the general formula (II) in a nitrogen stream And reacting with an aromatic amine derivative of formula (III) using trifluoro acetic acid as a catalyst to prepare a diethyl 2,5-diilino-3,6-dihydroterephthalate derivative of formula (VI). do. The aromatic amine of the general formula (III) used at this time is 5-aminoindan, 3,4- (methylenedioxy) aniline, 2-aminofluorene or 3-amino-9-ethylcarbazole, and A in general formula (VI) Represents cyclopentyl, methylenedioxy, indanyl or N-ethyl indolyl and cycloalkyl and aryl groups.

제2공정에서 일반식(VI)의 화합물을 고비점(250-257℃)의 비페닐 23.5%와 디페닐에테르 76.5%의 혼합용액으로 이루어진 공지의 다우텀 A를 용매로 사용하여 질소기류하에서 250-257℃에서 1시간동안 반응시켜서 일반식(VIII)의 6,13-디히드로 퀴나크리돈 유도체를 수득한다. 일반식(VII)에서 A는 일반식(VI)에서와 동일하다.In the second step, the compound of formula (VI) was dissolved in a nitrogen stream using a known Doomtum A consisting of a mixed solution of high boiling point (250-257 ° C.) biphenyl 23.5% and diphenyl ether 76.5% as a solvent. Reaction at −257 ° C. for 1 hour gives a 6,13-dihydro quinacridone derivative of the general formula (VIII). In formula (VII), A is the same as in formula (VI).

제3공정에서 일반식(VII)의 6,13-디히드로 퀴나크리돈 유도체를 에탄올, 물 및 수산화나트륨 용액과 메타-니트로 벤젠술폰산 나트륨염을 사용하여 산화시켜서 일반식(I)의 새로운 알파형 퀴나크리돈계 유도체를 제조한다. 여기서 A는 일반식(VI) 또는 일반식(VII)에서와 동일하다.In the third step, the 6,13-dihydroquinacridone derivative of formula (VII) was oxidized using ethanol, water and sodium hydroxide solution and meta-nitrobenzenesulfonic acid sodium salt to form a new alpha form of formula (I). To prepare a quinacridone derivative. Where A is the same as in formula (VI) or in formula (VII).

한편 제조한 새로운 일반식(I)의 알파형 퀴나크리돈계 유도체들는 X-선 분말회절접에 의해 다음과 같이 표시된다.Meanwhile, the alpha-quinacridone derivatives of the general formula (I) prepared are represented as follows by X-ray powder diffraction.

[표 1. 2 : 3, 9 : 10]Table 1. 2: 3, 9: 10]

디시클로펜틸 퀴나크리돈Dicyclopentyl quinacridone

Figure kpo00009
Figure kpo00009

Figure kpo00010
Figure kpo00010

[표 2. 2 : 3, 9 : 10][Table 2. 2: 3, 9: 10]

디메틸렌디옥시 퀴나크리돈Dimethylenedioxy quinacridone

Figure kpo00011
Figure kpo00011

Figure kpo00012
Figure kpo00012

[표 3. 2 : 3, 9 : 10][Table 3. 2: 3, 9: 10]

디(1', 2'-인다닐)퀴나크리돈Di (1 ', 2'-indanyl) quinacridone

Figure kpo00013
Figure kpo00013

Figure kpo00014
Figure kpo00014

[표 4. 2 : 3, 9 : 10]Table 4. 2: 3, 9: 10]

디[2',3'-(N-에틸인돌린)]퀴나크리돈Di [2 ', 3'-(N-ethylindolin)] quinacridone

Figure kpo00015
Figure kpo00015

다음 실시예는 본 발명을 더욱 상세히 예증하여 줄 것이며, 실시예 중에서 부로 표시된 것은 중량부를 의미한다.The following examples will illustrate the present invention in more detail, and the parts indicated in parts in the examples mean parts by weight.

[실시예 1]Example 1

500ML의 3구 둥근 플라스크에 온도계, 환류냉각기 및 딘-스타크 분류관을 장치한 후 틀루엔 150부를 가하고 질소가스를 통과시키면서 디에틸 1,4-디시클로헥산디온-2,5-디카르복실ㄹ이트 25.6부(0.1Mol)를 반응조에 가한 후 가열하여 용해시킨다. 계속해서 5-아미노인단 28부를 가하여 용해시키고 촉매인 트리플루오로 아세트산 0.5부를 가한 후 가열 환류시킨다. 이때 생성되는 물을 딘-스타크 분류관을 사용해서 제거시킨다.A 500 ml three-necked round flask equipped with a thermometer, a reflux condenser and a Dean-Stark tube, 150 parts of toluene was added and diethyl 1,4-dicyclohexanedione-2,5-dicarboxyl was added while passing through nitrogen gas. 25.6 parts (0.1 Mol) of acid were added to the reactor and then heated to dissolve. Subsequently, 28 parts of 5-aminoindan are added to dissolve, and 0.5 part of trifluoro acetic acid as a catalyst is added, followed by heating to reflux. The resulting water is removed using a Dean-Stark tube.

반응물을 2시간 후에 질소가스를 통과시키면서 천천히 냉각시키고, 메틸알코올 200부를 가한 후 여과하여 디에틸 2,5-디아미노인다닐-3,6-디히드로테레프탈레이트(VI) 45부(92.6%)를 수득한다.After 2 hours, the reaction product was slowly cooled while passing through nitrogen gas, 200 parts of methyl alcohol was added, followed by filtration, and 45 parts of diethyl 2,5-diaminoindanyl-3,6-dihydroterephthalate (VI) (92.6%). To obtain.

Figure kpo00016
Figure kpo00016

실시예 2에서 4까지의 유도체는 실시예 1과 동일한 방법으로 제조한다.Derivatives of Examples 2 to 4 are prepared in the same manner as in Example 1.

Figure kpo00017
Figure kpo00017

[실시예 5]Example 5

500ML의 3구 둥근 플라스크에 환류냉각기를 장착한 후 디에틸 2,5-디아미노인다닐-3,6-디히드로테레프탈레이트 45부를 가하고 질소가스를 통과시키면서 고비점의 비페닐과 디페닐에테르 혼합용액 270부를 가한 후 가열시킨다. 이때의 온도는 250-255℃이다.A reflux condenser was mounted in a 500 mL three-necked flask, and 45 parts of diethyl 2,5-diaminoindanyl-3,6-dihydroterephthalate was added, and high boiling point biphenyl and diphenyl ether were mixed while passing through nitrogen gas. 270 parts of solution are added and then heated. The temperature at this time is 250-255 degreeC.

동온도에서 1.5-2시간 교반시킨 후 반응물을 질소가스를 통과시키면서 냉각시킨다. 여기에 에탄올 200부를 가한 후 여과하여 2 : 3, 9 : 10-디스클로펜틸-6,13-디히드로 퀴나크리돈(VI) 28.5부(78%)를 수득한다.After stirring for 1.5-2 hours at the same temperature, the reaction is cooled while passing through nitrogen gas. 200 parts of ethanol was added thereto, followed by filtration to obtain 28.5 parts (78%) of 2: 3, 9: 10-disclopentyl-6,13-dihydroquinacridone (VI).

Figure kpo00018
Figure kpo00018

실시예 6에서 8까지의 유도체들은 실시예 5와 동일한 방법으로 제조한다.Derivatives of Examples 6 to 8 are prepared in the same manner as in Example 5.

Figure kpo00019
Figure kpo00019

[실시예 6]Example 6

500ML의 3구 둥근 플라스크에 환류냉각기를 장치하고, 2 : 3,9 : 10-디시클로펜틸-6,13-디히드로 퀴나크리돈 10부를 가하고 에탄올 200부와 물 25부에 수산화나트륨 4부를 용해한 용액을 가한 후 실온에서 20분동안 교반시킨다. 여기에 메타-니트로벤젠술폰산 나트륨염 20부를 분말상태로 가한 후 가열 환류시킨다. 반응시간은 3시간이 소요된다.A reflux condenser was installed in a 500 mL three-necked flask, 10 parts of 2: 3,9: 10-dicyclopentyl-6,13-dihydroquinacridone were added, and 4 parts of sodium hydroxide were dissolved in 200 parts of ethanol and 25 parts of water. The solution is added and stirred at room temperature for 20 minutes. 20 parts of sodium meta-nitrobenzenesulfonic acid salts are added to powder form, and it heats and refluxs. The reaction time is 3 hours.

반응물을 3시간 후 냉각시키면서 물 200부를 가하고 수분교반 후 여과시켜서 명적색을 띤 알파형의 2 : 3,9 : 10-디시클로펜틸 퀴나크리돈(Ⅰ) 9.5부(95%)를 수득한다.After the reaction was cooled after 3 hours, 200 parts of water was added thereto, followed by filtration of water, followed by filtration to obtain 9.5 parts (95%) of a bright red alpha-type 2: 3,9: 10-dicyclopentyl quinacridone (I).

실시예 10에서 12까지의 유도체들은 실시예 9와 동일한 방법으로 제조한다.Derivatives of Examples 10 to 12 are prepared in the same manner as in Example 9.

Figure kpo00020
Figure kpo00020

Claims (6)

일반식(I)로 표시되는 알파형 퀴나크리돈계 유도체.Alpha-type quinacridone derivative represented by general formula (I).
Figure kpo00021
Figure kpo00021
 일반식(I)에 있어서 A는 하나 또는 두개의 고리를 가진 시클로펜틸, 메틸렌디옥시, 인다닐 또는 N-에틸 인돌릴기를 나타낸다.In formula (I), A represents a cyclopentyl, methylenedioxy, indanyl or N-ethyl indolyl group having one or two rings. 일반식(II)의 디에틸, 1,4-디시클로헥산디온-2,5-디카르복실레이트와 일반식(III)의 방향족아민 유도체를 반응시켜 일반식(VI)의 디에틸 2,5-디아닐리노-3,6-디히드로프탈레이트 유도체를 제조하는 제1공정과 일반식(VI)의 디에틸 2,5-디아닐리노-3,6-디히드로프탈레이트 유도체를 고리화 반응으로 일반식(VII)의 6,13-디히드로 퀴나크리돈 유도체를 제조하는 제2공정과 일반식(VII)의 6,13-디히드로 퀴나크리돈 유도체를 메타-니트로벤젠술폰산 나트륨염과 반응시켜 일반식(I)의 알파형 퀴나크리돈계 유도체를 제조하는 제3공정으로 이루어진 것이 특징인 일반식(I)의 알파형 퀴나크리돈계 유도체의 제조방법.Diethyl 2,5 of general formula (VI) by reacting diethyl, 1,4-dicyclohexanedione-2,5-dicarboxylate of general formula (II) with an aromatic amine derivative of general formula (III) The first step of preparing a dianilino-3,6-dihydrophthalate derivative and the diethyl 2,5-dianilin-3,6-dihydrophthalate derivative of the general formula (VI) by cyclization reaction A second process for preparing a 6,13-dihydro quinacridone derivative of formula (VII) and a 6,13-dihydro quinacridone derivative of general formula (VII) are reacted with a meta-nitrobenzenesulfonic acid sodium salt to give a general A method for producing an alpha type quinacridone derivative of general formula (I), comprising the third step of preparing an alpha type quinacridone derivative of formula (I).
Figure kpo00022
Figure kpo00022
Figure kpo00023
Figure kpo00023
Figure kpo00024
Figure kpo00024
Figure kpo00025
Figure kpo00025
 일반식(Ⅰ)에 있어서 A는 하나 또는 두개의 고리를 가진 시클로펜틸, 메틸렌디옥시, 인다닐 또는 N-에틸 인돌릴기를 나타낸다. 일반식(Ⅲ)과 일반식(Ⅵ)과 일반식(Ⅶ)에 있어서 A는 일반식(Ⅰ)과 동일하다.In the general formula (I), A represents a cyclopentyl, methylenedioxy, indanyl or N-ethyl indolyl group having one or two rings. In general formula (III), general formula (VI), and general formula (iii), A is the same as general formula (I). 제2항에 있어서, 제1공정에서 일반식(Ⅲ)의 방향족아민 유도체로 5-아미노인단, 3, 4-(메틸렌디옥시)아닐린, 2-아미노플루오렌, 3-아미노-9-에틸카바졸 중에서 선택하여 반응시키는 것을 특징으로 하는 일반식(Ⅰ)의 알파형 퀴나크리돈계 유도체의 제조방법.The aromatic amine derivative of the general formula (III) in the first step is 5-aminoindan, 3,4- (methylenedioxy) aniline, 2-aminofluorene, 3-amino-9-ethylcarba A method for producing an alpha type quinacridone derivative of formula (I), characterized by reacting by selecting from sol. 제2항에 있어서, 제1공정에서 톨루엔이나 크실렌을 용매로 사용하고, 트리플루오로 아세트산을 촉매로 사용하는 것을 특징으로 하는 일반식(Ⅰ)의 알파형 퀴나크리돈계 유도체의 제조방법.The method for producing an alpha-quinacridone derivative of formula (I) according to claim 2, wherein toluene or xylene is used as a solvent and trifluoro acetic acid is used as a catalyst in the first step. 제2항에 있어서, 제2공정에서 다우럼 A를 용매로 사용하여 250-257℃에서 1시간동안 반응시키는 것을 특징으로 하는 일반식(Ⅰ)의 알파형 퀴나크리돈계 유도체의 제조방법.The method for preparing alpha-quinacridone derivatives of the general formula (I) according to claim 2, wherein Dowurum A is used as a solvent and reacted at 250-257 ° C for 1 hour. 제2항에 있어서, 제3공정에서 에탄올, 물 및 수산화나트륨 용액과 메타-니트로벤젠술폰산 나트륨염을 반응시키는 것을 특징으로 하는 일반식(Ⅰ)의 알파형 퀴나크리돈계 유도체의 제조방법.The method for producing an alpha-quinacridone derivative of the general formula (I) according to claim 2, wherein the ethanol, water, sodium hydroxide solution and meta-nitrobenzenesulfonic acid sodium salt are reacted in the third step.
KR1019900015291A 1990-09-26 1990-09-26 New alpha-tape quinacridone derivatives and preparation thereof KR930010503B1 (en)

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