KR100578318B1 - Process for preparing disperse dyes - Google Patents

Process for preparing disperse dyes Download PDF

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KR100578318B1
KR100578318B1 KR1020040095555A KR20040095555A KR100578318B1 KR 100578318 B1 KR100578318 B1 KR 100578318B1 KR 1020040095555 A KR1020040095555 A KR 1020040095555A KR 20040095555 A KR20040095555 A KR 20040095555A KR 100578318 B1 KR100578318 B1 KR 100578318B1
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structural formula
represented
general formula
following structural
diphenyl carbonate
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박정빈
정윤호
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주식회사 잉크테크
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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
    • C09B67/00Influencing 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
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008Preparations of disperse dyes or solvent dyes
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/02Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
    • B01J23/04Alkali metals
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/20Carbon compounds
    • B01J27/232Carbonates
    • 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
    • C09B1/00Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/02Hydroxy-anthraquinones; Ethers or esters thereof
    • C09B1/06Preparation from starting materials already containing the anthracene nucleus
    • C09B1/14Dyes containing ether groups

Abstract

본 발명은 분산염료 제조방법에 관한 것이다. 보다 상세하게는 안트라퀴논 구조를 갖는 화합물을 일반식(5)의 디페닐카르보네이트와 반응시켜 하기 일반식(1)과 일반식(2)의 구조를 갖는 분산염료 제조방법을 제공하는 것이다.The present invention relates to a process for producing disperse dyes. More specifically, the present invention provides a process for producing a disperse dye having a structure represented by the following general formula (1) and general formula (2) by reacting a compound having an anthraquinone structure with diphenyl carbonate of the general formula (5).

Figure 112004054194540-pat00001
Figure 112004054194540-pat00001

Figure 112004054194540-pat00002
Figure 112004054194540-pat00002

Figure 112004054194540-pat00003
Figure 112004054194540-pat00003

상기 식에서, X는 산소원자 또는 황원자, R1은 C2~C6알킬렌이며, R2 는 C2~C6알킬렌, n은 1 또는 2이다.X is an oxygen atom or a sulfur atom, R 1 is C 2 -C 6 alkylene, R 2 is C 2 -C 6 alkylene, and n is 1 or 2.

본 발명을 통해서 종래의 기술보다 안전하고 간단한 공정으로 상기 일반식(1)과 일반식(2)의 분산염료를 높은 수율로 제조할 수 있다.According to the present invention, the dispersion dyes of the general formula (1) and the general formula (2) can be produced in a high yield with a safer and simpler process than the conventional technique.

분산염료, 안트라퀴논, 카르보네이트, 디페닐카르보네이트Disperse dyes, anthraquinone, carbonates, diphenyl carbonate

Description

분산염료의 제조방법 {PROCESS FOR PREPARING DISPERSE DYES}PROCESS FOR PREPARING DISPERSE DYES [0002]

분산염료는 물에 불용성을 갖는 염료로서 물에 분산된 상태에서 아세테이트, 나이론, 폴리에스테르 섬유의 염색에 주로 사용되고 있는 염료를 말한다. 즉 분산염료는 물에 녹지 않는 미세한 분말로, 계면활성제 등의 분산제를 사용하여 물에 콜로이드 상태로 분산시켜, 섬유에 염착시키는 염료이다. 아조, 안트라퀴논, 아조메틴, 니트로계 염료가 이에 해당되며 아조 및 안트라퀴논계 염료가 주류를 이룬다.Disperse dyes are dyes which are insoluble in water and which are mainly used for dyeing acetate, nylon and polyester fibers in a state of being dispersed in water. That is, the disperse dye is a fine powder that does not dissolve in water and disperses it in a colloidal state in water using a dispersant such as a surfactant to dye the fiber. These include azo, anthraquinone, azomethine, and nitro-based dyes, which are dominated by azo and anthraquinone dyes.

본 발명은 다음 일반식(1)과 일반식(2)로 표시되는 안트라퀴논 분산염료 제조방법에 관한 것이다. 보다 상세하게는 하기구조의 분산염료를 제조함에 있어 각각 안트라퀴논 구조의 화합물과 디페닐카르보네이트를 반응시키는 방법으로 종래의 제조방법보다 우수한 제조방법을 제공하는 것이 특징이다.The present invention relates to a process for producing an anthraquinone disperse dye represented by the following general formula (1) and general formula (2). More particularly, the present invention is characterized by providing a method of preparing a dispersion dye having the following structure by reacting a compound having an anthraquinone structure with diphenyl carbonate, respectively, as compared with the conventional method.

Figure 112004054194540-pat00004
Figure 112004054194540-pat00004

Figure 112004054194540-pat00005
Figure 112004054194540-pat00005

상기 식에서, X는 산소원자 또는 황원자, R1은 C2~C6알킬렌이며, R2 는 C2~C6알킬렌, n은 1 또는 2이다.X is an oxygen atom or a sulfur atom, R 1 is C 2 -C 6 alkylene, R 2 is C 2 -C 6 alkylene, and n is 1 or 2.

상기 일반식(1)과 일반식(2)로 표시되는 분산염료는 미국 특허공보 제 3,689,510호(1972년)에 최초 공개되었으며, 이후 미국 특허공보 3,767,681호(1973년), 미국 특허공보 3,769,305호(1973년), 미국 특허공보 3,803,168호(1974년), 미국 특허공보 3,806,524호(1974년), 미국 특허공보 4,804,767호(1989년)에서는 일반식(1)과 일반식(2)의 분산염료를 제조함에 있어, 각각 개별적인 제조 조건은 다르나, 공통적으로 안트라퀴논 구조의 화합물에 할로포르메이트 구조의 화합물인 하기의 일반식(6)을 사용하여 합성한다고 기술하고 있다.Disperse dyes represented by the general formulas (1) and (2) were first disclosed in U.S. Patent No. 3,689,510 (1972), and US Pat. No. 3,767,681 (1973) and U.S. Patent No. 3,769,305 (1) and the general formula (2) in US Pat. No. 3,803,168 (1974), US Pat. No. 3,806,524 (1974) and US Pat. No. 4,804,767 , It is described that they are synthesized by using a compound represented by the following general formula (6), which is a compound having a haloformate structure, in common to an anthraquinone structure compound, although their respective production conditions are different.

Figure 112004054194540-pat00006
Figure 112004054194540-pat00006

그러나, 일반식(6)의 페닐클로로포르메이트는 반응성이 매우 높아 저장 및 사용시 무수환경을 필요로 하는 등의 어려움이 있고, 이를 이용하여 분산염료를 합성하는 공정 중 산증기가 발생하기 때문에 유기 혹은 무기 염기를 산억제제로서 당량 또는 당량 이상을 사용하여야 한다. 또한 반응 후 미반응 잔존물에 의해 염료 본체의 아로마틱 아민과 반응하여 변색현상이 일어나는 등의 단점을 갖고 있다.However, since the phenyl chloroformate of the general formula (6) has a very high reactivity, there is a difficulty in requiring an anhydrous environment during storage and use, and since an acidosis occurs in the process of synthesizing a disperse dye, The base should be used in an equivalent or equivalent amount as an acid inhibitor. And also has the disadvantage of causing discoloration by reacting with the aromatic amine of the dye main body due to unreacted remnants after the reaction.

본 발명은 상기의 문제점들을 해결하기 위한 방법으로 일반식(5)의 디페닐카르보네이트를 사용하는 것으로 분산염료의 합성 후에 간단한 세정으로도 쉽게 제거할 수 있는 알칼리 염기를 촉매로 사용함으로써 산증기의 발생 없이 안전하게 원하는 화합물을 얻을 수 있는 제조 방법을 제공한다.The present invention uses a diphenyl carbonate of the general formula (5) as a method for solving the above problems, and it is an object of the present invention to provide an acidic vapor And a desired compound can be obtained safely without occurrence of the above-mentioned problems.

또한 메탄올에 의한 재침전 및 세정을 통해 합성 부산물의 제거가 용이하여 종래의 제조 방법보다 간단한 공정으로 분산염료를 얻을 수 있다. 또한 종래의 제조 방법보다도 비교적 높은 수율을 얻을 수 있다.In addition, since the synthesis by-products can be easily removed by reprecipitation and washing with methanol, a dispersion dye can be obtained by a simpler process than the conventional production method. In addition, a relatively high yield can be obtained as compared with the conventional production method.

본 발명의 목적은 합성 원재료 및 제조 방법의 변경을 통하여 특수한 설비 없이 종래 제조 방법의 문제점을 극복하고, 보다 안전하고 간단한 공정으로 일반식(1)과 일반식(2)의 분산염료를 높은 수율로 얻을 수 있는 방법을 제공하고자 하는 것이다.
It is an object of the present invention to overcome the disadvantages of the conventional production method without special equipment through modification of the synthetic raw materials and the manufacturing method and to provide a dispersion dye of the general formula (1) and the general formula (2) And to provide a method that can be obtained.

상기 기술적 과제를 이루고자 본 발명에서 제공하는 제조 방법은 일반식(3)과 일반식(4)의 안트라퀴논 화합물에 각각 일반식(5)의 디페닐카르보네이트를 촉매 하에서 반응시켜 일반식(1)과 일반식(2)의 분산염료를 얻는 단계로 이루어지는 것 을 특징으로 한다.In order to accomplish the above object, the present invention provides a process for producing an anthraquinone compound represented by the general formula (1) by reacting an anthraquinone compound of the general formula (3) and a diphenyl carbonate of the general formula (5) ) And a disperse dye represented by the general formula (2).

Figure 112004054194540-pat00007
Figure 112004054194540-pat00007

Figure 112004054194540-pat00008
Figure 112004054194540-pat00008

Figure 112004054194540-pat00009
Figure 112004054194540-pat00009

Figure 112004054194540-pat00010
Figure 112004054194540-pat00010

Figure 112004054194540-pat00011
Figure 112004054194540-pat00011

상기 식에서, X는 산소원자 또는 황원자, R1은 C2~C6알킬렌이며, R2 는 C2~C6알킬렌, n은 1 또는 2이다.X is an oxygen atom or a sulfur atom, R 1 is C 2 -C 6 alkylene, R 2 is C 2 -C 6 alkylene, and n is 1 or 2.

전술한 종래의 방법에 따르면 일반식(3)과 일반식(4)의 안트라퀴논 화합물에 각각 일반식(6)의 페닐클로로포르메이트를 용제 상에서 반응하여 일반식(1)과 일반식(2)의 분산염료를 얻는다. 본 발명에서는 전술한 일반식(6)의 페닐클로로포르메 이트를 대신하여 일반식(5)의 디페닐카르보네이트와 알칼리 촉매를 사용함으로써 공정상의 안정성과 용이성을 확보하였고, 특별한 장치 없이 교반기만으로 높은 수율의 분산염료 합성이 가능하게 되었다. (1) and (2) by reacting an anthraquinone compound represented by the general formula (3) and an anthraquinone compound represented by the general formula (4) ≪ / RTI > In the present invention, by using the diphenyl carbonate of formula (5) and an alkali catalyst in place of the phenyl chloroformate of the above-mentioned general formula (6), the stability and easiness of the process are ensured and only the agitator A high yield of disperse dye synthesis has become possible.

본 발명에서 제공하는 새로운 제조방법을 상세하게 기술하면, 먼저 일반식(3) 또는 일반식(4)의 구조를 갖는 안트라퀴논계 물질과 이에 대해 일반식(5)의 디페닐카르보네이트를 1.5~2당량으로 혼합하여 적절한 용매에 용해한 후 적정온도로 승온하여 교반한다. 계속해서 축합반응에 사용하기 적절한 촉매를 투입하여 교반한 다음 이 반응액을 메탄올에 부어 침전시켜 상기의 일반식(1) 또는 일반식(2)의 염료 결정을 얻을 수 있다.First, an anthraquinone-based material having a structure represented by the general formula (3) or (4) and a diphenyl carbonate represented by the general formula (5) To 2 equivalents, dissolved in an appropriate solvent, heated to an appropriate temperature and stirred. Subsequently, a catalyst suitable for use in the condensation reaction is added and stirred, and the reaction solution is poured into methanol to precipitate the dye crystals of the formula (1) or (2).

본 발명에 사용하는 용제는 반응물을 잘 용해할 수 있으며, 메탄올 등의 알코올류와 친화성이 있는 것으로써, 바람직하게는 아세톤, 2-부타논 등의 케톤류와 디에틸에테르, 디옥산 등의 에테르류를 사용할 수 있다. The solvent used in the present invention can dissolve reactants well and has affinity with alcohols such as methanol. The solvent is preferably a ketone such as acetone or 2-butanone, an ether such as diethyl ether or dioxane Can be used.

또한, 본 발명에 사용하는 촉매는 수산화리튬, 수산화나트륨, 수산화칼륨 등의 수산화물과 탄산나트륨, 탄산칼륨, 탄산세슘 등의 탄산화물을 1~20중량부로 사용하며, 바람직하게는 5~15중량부로 사용한다.In addition, the catalyst used in the present invention is prepared by using hydroxides of lithium hydroxide, sodium hydroxide, potassium hydroxide and the like and carbonates such as sodium carbonate, potassium carbonate and cesium carbonate in an amount of 1 to 20 parts by weight, preferably 5 to 15 parts by weight do.

반응 온도는 50~110℃가 바람직하며, 바람직하게는 70~90℃로, 사용하는 용제에 따라 조절한다.The reaction temperature is preferably from 50 to 110 ° C, and preferably from 70 to 90 ° C, depending on the solvent used.

최종 합성된 분산염료의 구조는 핵자기공명 분광분석기와, 적외선 분광분석기로 확인을 하였으며, 순도는 자외선 분광분석기와 고성능 액체크로마토크래피로 확인하였다.The structure of the finally synthesized disperse dye was confirmed by nuclear magnetic resonance spectrometer and infrared spectrometer. The purity was confirmed by ultraviolet spectrometer and high performance liquid chromatography.

이하 실시예 및 비교예를 통해 본 발명을 더욱 구체적으로 설명한다. 그러나 다음 실시예에 의해서 본 발명이 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. However, the present invention is not limited by the following examples.

실시예 1Example 1

둥근바닥 플라스크에 교반기를 장치한 후, 1-아미노-4-하이드록시-2-b-하이드록시에톡시안트라퀴논 200g과 디페닐카르보네이트 280g을 1,4-디옥산 800g에 혼합하고 80℃로 승온하여 교반한다. 수산화칼륨 10g을 분말상으로 첨가하고 80~85℃에서 3시간 동안 교반한다. 반응액을 메탄올 3000g에 부어 침전시킨 후 상온에서 1시간 정도 방치한 다음 생성된 염료결정을 감압상에서 여과하고 2000g의 정수로 2회 세정한다. 메탄올 500g으로 1회 세정하고 건조하여 밝은 적색의 염료 249.2g을 얻었다. 수율은 89.0%이다.A round bottom flask was equipped with a stirrer, and then 200 g of 1-amino-4-hydroxy-2-b-hydroxyethoxyanthraquinone and 280 g of diphenyl carbonate were mixed with 800 g of 1,4-dioxane, And stirred. 10 g of potassium hydroxide is added in powder form, and the mixture is stirred at 80 to 85 ° C for 3 hours. The reaction solution is poured into 3000 g of methanol to precipitate and then left at room temperature for about 1 hour. The resulting dye crystals are filtered off under reduced pressure and washed twice with an aqueous solution of 2000 g. Washed once with 500 g of methanol and dried to obtain 249.2 g of a bright red dye. The yield is 89.0%.

상기 화합물로 브로모칼륨 펠렛을 제조하여 적외선 분광분석기(FT/IR-480 plus, 자스코(JASCO)사)를 사용하여 실온에서 주사회수 16회, 분해능 4cm-1의 조건으로 적외선 분광분석을 하였다. 핵자기공명 분광분석으로는 1H-NMR(VARIAN 200MHz, 바리안(VARIAN)사)을 이용하였고, 용매로는 CDCl3 기준물질로는 테트라메틸실란을 사용하였다.Bromo-potassium pellets were prepared from the above compounds and subjected to infrared spectroscopic analysis under the conditions of a number of injections of 16 times and a resolution of 4 cm -1 at room temperature using an infrared spectrometer (FT / IR-480 plus, JASCO). 1 H-NMR (VARIAN 200 MHz, VARIAN) was used for the nuclear magnetic resonance spectroscopy and tetramethylsilane was used as the solvent for the CDCl 3 reference material.

IR(KBr) : vmax = 1762cm-1 (-O-CO-O-)IR (KBr): v max = 1762 cm -1 (-O- CO- O-)

1H-NMR : d(ppm): 4.39(2H, t, -OCH2-), 4.75(2H, t, -CH2-OCO2-), 6.59(1H, s, ArH), 7.15~7.50(5H, m, -O-Phenyl), 7.79(2H, m, ArH), 8.40(2H, m, ArH) 1 H-NMR: d (ppm ): 4.39 (2H, t, -OCH 2 -), 4.75 (2H, t, -CH 2 -OCO 2 -), 6.59 (1H, s, ArH), 7.15 ~ 7.50 ( (2H, m, ArH), 8.40 (2H, m, ArH)

UV : lmax = 511.00nm (400nm ~ 600nm)UV: lmax = 511.00 nm (400 nm to 600 nm)

비교예 1Comparative Example 1

둥근바닥 플라스크에 교반기를 장치한 후, 10g의 1-아미노-4-하이드록시-2-b-하이드록시에톡시안트라퀴논을 40g의 톨루엔에 분산하고 산억제제로서 3.4g의 피리딘을 첨가한다. 이 혼합용액을 70℃에서 충분한 교반을 하고, 10.5g의 페닐클로로포르메이트를 10g의 톨루엔에 희석하여 천천히 투입한다. 페닐클로로포르메이트의 투입이 끝나면 반응액을 70℃에서 1시간 교반한다. 반응액을 20℃로 냉각하고 메탄올 300g에 침전시키고 정수와 메탄올로 세정하여 황색의 부 반응물이 다량 함유된 상태로 적색염료를 얻었다. 이 혼합물을 액체크로마토그래피로 정제하여 11.0g의 적색염료를 얻었다. 수율은 79%이다.After placing the stirrer in a round bottom flask, 10 g of 1-amino-4-hydroxy-2-b-hydroxyethoxyanthraquinone is dispersed in 40 g of toluene and 3.4 g of pyridine is added as an acid inhibitor. The mixed solution was sufficiently stirred at 70 ° C, and 10.5 g of phenyl chloroformate was diluted in 10 g of toluene and slowly added. When the introduction of the phenyl chloroformate is completed, the reaction solution is stirred at 70 ° C for 1 hour. The reaction solution was cooled to 20 占 폚, precipitated in 300 g of methanol, and washed with water and methanol to obtain a red dye in a state containing a large amount of yellow adverse reaction products. This mixture was purified by liquid chromatography to obtain 11.0 g of a red dye. The yield is 79%.

비교예 2Comparative Example 2

둥근바닥 플라스크에 교반기를 장치한 후, 10g의 1-아미노-4-하이드록시-2-b-하이드록시에톡시안트라퀴논을 40g의 톨루엔에 분산하고 산억제제로서 12.8g의 피리딘을 첨가한다. 이 혼합용액을 70℃에서 충분한 교반을 하고, 7.9g의 페닐클로로포르메이트를 10g의 톨루엔에 희석하여 천천히 투입한다. 페닐클로로포르메이트 의 투입이 끝나면 반응액을 70℃에서 2시간 내지 3시간 교반한다. 반응액을 20℃로 냉각하고 메탄올 300g에 침전시킨 후 침전물을 여과하고 정수와 메탄올로 세정하여 10.7g의 적색염료를 얻었다. 수율은 76%이다.After placing the stirrer in a round bottom flask, 10 g of 1-amino-4-hydroxy-2-b-hydroxyethoxyanthraquinone is dispersed in 40 g of toluene and 12.8 g of pyridine is added as an acid inhibitor. The mixed solution was sufficiently stirred at 70 ° C, and 7.9 g of phenyl chloroformate was diluted in 10 g of toluene and slowly added. When the introduction of the phenyl chloroformate is completed, the reaction solution is stirred at 70 占 폚 for 2 hours to 3 hours. The reaction solution was cooled to 20 DEG C and precipitated in 300 g of methanol. The precipitate was filtered and washed with water and methanol to obtain 10.7 g of a red dye. The yield is 76%.

실시예 2~8Examples 2 to 8

실시예 1의 1-아미노-4-하이드록시-2-b-하이드록시에톡시안트라퀴논 대신 <표1>의 안트라퀴논 화합물과 디페닐카르보네이트를 사용하여 실시예 1과 동일한 방법으로 염료를 합성하였다.A dye was prepared in the same manner as in Example 1 except that the anthraquinone compound of Table 1 and diphenyl carbonate were used instead of 1-amino-4-hydroxy-2-b-hydroxyethoxyanthraquinone of Example 1 Were synthesized.

실시예Example 안트라퀴논 화합물Anthraquinone compound 색상color 수율(%)yield(%) 22

Figure 112004054194540-pat00012
Figure 112004054194540-pat00012
적색Red 88%88% 33
Figure 112004054194540-pat00013
Figure 112004054194540-pat00013
적색Red 88%88%
44
Figure 112004054194540-pat00014
Figure 112004054194540-pat00014
적색Red 89%89%
55
Figure 112004054194540-pat00015
Figure 112004054194540-pat00015
자색Purple 89%89%
66
Figure 112004054194540-pat00016
Figure 112004054194540-pat00016
자색Purple 88%88%
77
Figure 112004054194540-pat00017
Figure 112004054194540-pat00017
적색Red 88%88%
88
Figure 112004054194540-pat00018
Figure 112004054194540-pat00018
청색blue 87%87%

상기 실시예 및 비교예에서 알 수 있듯이, 일반식(5)의 디페닐카르보네이트와 간단한 세정으로도 쉽게 제거할 수 있는 알칼리 염기를 촉매로 사용함으로써 산증기의 발생이 없는 안전한 공정으로 원하는 화합물을 얻을 수 있으며, 또한 메탄올에 의한 재침전 및 세정 만으로도 합성 부산물의 제거가 용이하여 종래의 제조 방법보다 간단한 공정으로 분산염료를 높은 수율로 얻을 수 있다.As can be seen from the above Examples and Comparative Examples, by using a diphenyl carbonate of the general formula (5) and an alkaline base which can be easily removed even by a simple rinse as a catalyst, a desired process And the synthesis by-products can be easily removed only by reprecipitation and washing with methanol, so that the dispersion dye can be obtained in a high yield with a simpler process than the conventional production method.

상기와 같이, 본 발명은 보다 안전하고 간단한 공정으로 분산염료를 높은 수율로 얻을 수 있는 방법을 제공할 수 있다.As described above, the present invention can provide a method for obtaining a dispersion dye at a high yield with a safer and simpler process.

Claims (5)

하기 구조식(3)으로 표시되는 안트라퀴논 화합물과 하기 구조식(5)로 표시되는 디페닐카르보네이트를 반응시켜, 하기 구조식(1)의 분산염료를 제조하는 것을 특징으로 하는 분산염료 제조방법.A process for producing a disperse dye, which comprises reacting an anthraquinone compound represented by the following structural formula (3) with a diphenyl carbonate represented by the following structural formula (5) to prepare a disperse dye represented by the following structural formula (1).
Figure 112004054194540-pat00019
Figure 112004054194540-pat00019
Figure 112004054194540-pat00020
Figure 112004054194540-pat00020
Figure 112004054194540-pat00021
Figure 112004054194540-pat00021
(상기 식에서, X는 산소원자 또는 황원자, R1은 C2~C6알킬렌 또는 티오알킬렌이며, n은 1 또는 2임).(Wherein X is an oxygen atom or a sulfur atom, R 1 is C 2 -C 6 alkylene or thioalkylene, and n is 1 or 2).
하기 구조식(4)으로 표시되는 안트라퀴논 화합물과 하기 구조식(5)로 표시되는 디페닐카르보네이트를 반응시켜, 하기 구조식(2)의 분산염료를 제조하는 것을 특징으로 하는 분산염료 제조방법.Wherein the anthraquinone compound represented by the following structural formula (4) and the diphenyl carbonate represented by the following structural formula (5) are reacted to prepare a disperse dye represented by the following structural formula (2).
Figure 112004054194540-pat00022
Figure 112004054194540-pat00022
Figure 112004054194540-pat00023
Figure 112004054194540-pat00023
Figure 112004054194540-pat00024
Figure 112004054194540-pat00024
(상기 식에서, R2는 C2~C6알킬렌이며, n은 1 또는 2임).(Wherein R 2 is C 2 -C 6 alkylene, and n is 1 or 2).
제 1항 또는 제 2항에 있어서, 구조식(3) 또는 구조식(4)로 표시되는 안트라퀴논 화합물과 구조식(5)로 표시되는 디페닐카르보네이트를 혼합하여 용제로 용해하는 단계; 승온하여 교반하는 단계; 축합반응에 사용되는 촉매를 투입하고 교반하여 반응액을 얻는 단계; 상기 반응액을 메탄올에 부어 침전시켜 구조식(1) 또는 구조식(2)로 표시되는 분산염료를 제조하는 것을 특징으로 하는 분산염료 제조방법.The method according to claim 1 or 2, wherein the anthraquinone compound represented by the structural formula (3) or (4) and the diphenyl carbonate represented by the structural formula (5) are mixed and dissolved in a solvent; Heating and stirring; Adding a catalyst used for the condensation reaction and stirring to obtain a reaction solution; The reaction solution is poured into methanol to precipitate to prepare a disperse dye represented by the structural formula (1) or (2). 제 3항에 있어서, 용제는 케톤류 화합물 또는 에테르류 화합물에서 선택되어 사용되는 것을 특징으로 하는 분산염료 제조방법.The method for producing a dispersion dye according to claim 3, wherein the solvent is selected from a ketone compound or an ether compound. 제 3항에 있어서, 촉매는 수산화리튬, 수산화나트륨, 수산화칼륨, 탄산나트륨, 탄산칼륨 또는 탄산세슘에서 선택되어 사용되는 것을 특징으로 하는 분산염료 제조방법.The method for producing a dispersion dye according to claim 3, wherein the catalyst is selected from lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate or cesium carbonate.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4080369A (en) * 1976-03-25 1978-03-21 Imperial Chemical Industries Limited Disperse anthraquinone dyestuffs
US4804767A (en) * 1986-08-08 1989-02-14 Ciba-Geigy Corporation Process for the preparation of disperse dyes
US7138414B2 (en) * 2002-07-12 2006-11-21 Sanofi-Aventis Deutschland Gmbh Heterocyclically substituted benzoylureas, process for their preparation and their use as pharmaceuticals

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4080369A (en) * 1976-03-25 1978-03-21 Imperial Chemical Industries Limited Disperse anthraquinone dyestuffs
US4804767A (en) * 1986-08-08 1989-02-14 Ciba-Geigy Corporation Process for the preparation of disperse dyes
US7138414B2 (en) * 2002-07-12 2006-11-21 Sanofi-Aventis Deutschland Gmbh Heterocyclically substituted benzoylureas, process for their preparation and their use as pharmaceuticals

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