KR102060607B1 - The preparing method of disperse orange dye - Google Patents

The preparing method of disperse orange dye Download PDF

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KR102060607B1
KR102060607B1 KR1020170183646A KR20170183646A KR102060607B1 KR 102060607 B1 KR102060607 B1 KR 102060607B1 KR 1020170183646 A KR1020170183646 A KR 1020170183646A KR 20170183646 A KR20170183646 A KR 20170183646A KR 102060607 B1 KR102060607 B1 KR 102060607B1
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formula
acid
coupler
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compound
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KR20190081250A (en
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윤양수
이원목
김용호
김창일
엄경섭
조재호
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아크로마코리아 주식회사
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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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3608—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered heterocyclic ring with only one nitrogen as heteroatom
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0805—Amino benzenes free of acid groups
    • C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
    • C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
    • C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
    • C09B29/0823—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by CN
    • C09B29/0826—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by CN having N(-alkenylene/-alkynylene-O)(-alkenylene/-alkynylene-CN)
    • 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
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye

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Abstract

본 발명의 오렌지색 분산 염료의 제조방법은 하기 식(2)의 커플러를 하기 식(4)의 화합물과 커플링 반응시켜 하기 식(I)의 오렌지색 분산 염료를 제조하는 것을 특징으로 한다:

Figure 112017130975760-pat00010

상기 식에서, X1,X2는 알킬 또는 할로겐이고, A는 산의 잔기, nT는 알킬렌카보네이트, 또는 알킬할라이드인 T로부터 유도된 치환기이고 n은 반복단위이다. The method for preparing an orange disperse dye of the present invention is characterized by preparing an orange disperse dye of formula (I) by coupling a coupler of formula (2) with a compound of formula (4):
Figure 112017130975760-pat00010

Wherein X 1, X 2 is alkyl or halogen, A is a residue derived from T, nT is an alkylene carbonate, or alkyl halide, and n is a repeating unit.

Description

오렌지색 분산 염료의 제조방법{THE PREPARING METHOD OF DISPERSE ORANGE DYE}Manufacturing method of orange disperse dye {THE PREPARING METHOD OF DISPERSE ORANGE DYE}

본 발명은 분산염료의 제조방법, 더욱 상세하게는 오렌지색의 발색을 하는 아조계 분산염료의 제조방법에 관한 것이다. The present invention relates to a method for producing a disperse dye, and more particularly to a method for producing an azo-based dye having an orange color.

분산 염료는 물에 녹지 않거나 또는 잘 녹지 않아서 미세한 가루로 만들고, 계면활성제 등의 분산제를 써서 물에 콜로이드에 가까운 상태로까지 분산시켜, 섬유 속에 염료를 용해시켜서 염착하는 염료이다. Disperse dyes are dyes that do not dissolve or dissolve well in water to make fine powder, and disperse dyes in fibers by dispersing them into a state near colloid in water using a dispersing agent such as a surfactant.

아세테이트 인견의 염색용으로 개발되었기 때문에 아세테이트염료라고도 한다. 모두 분자량이 그다지 크지 않은 아민이며 분자 내에 수산기, 에테르, 에스테르 등의 약한 친수기를 포함하는 것은 보통이지만, 술폰기와 같은 강한 친수기를 포함하지 않는다. 초기 단계에는 아세테이트 섬유의 염색용으로 개발되었으나, 이 후 폴리에스테르 섬유의 출현과 더불어, 염착성이나 견뢰도가 우수한 폴리에스테르용이 개발되었다. 현재에는 폴리에스테르 섬유가 합성섬유 가운데 가장 생산량이 많은 섬유로 발전하게 되어, 90% 이상을 폴리에스테르용 분산염료가 점유하고 있다. 화학 구조에 따라 분류를 하면, 벤젠아조계, 복소환아조계, 아조트라퀴논계, 축합계 등으로 다양하지만, 생산량으로 보면 아조계 염료가 전체의 약 70% 이상을 차지하고 있다. It is also called acetate dye because it was developed for dyeing acetate dogs. All of them are amines having a low molecular weight and usually contain weak hydrophilic groups such as hydroxyl groups, ethers, esters, etc., but do not contain strong hydrophilic groups such as sulfone groups. In the early stages, it was developed for dyeing acetate fibers, but with the advent of polyester fibers, polyester for excellent dyeing and fastness were developed. At present, polyester fiber is developed into the most productive fiber among synthetic fibers, and more than 90% is occupied by dispersion dyes for polyester. When classified according to chemical structure, it is diverse as benzene azo system, heterocyclic azo system, azotraquinone system, condensation system and so on.

한국특허등록 10-0949416Korea Patent Registration 10-0949416 한국특허등록 10-1416893Korea Patent Registration 10-1416893

본 발명은 견뢰도가 우수하고 우수한 발색성을 나타내는 오렌지색 분산 염료의 제조방법을 제공하는 것이다. The present invention is to provide a method for producing an orange disperse dye having excellent fastness and excellent color development.

본 발명의 오렌지색 분산 염료의 제조방법은 하기 식(2)의 커플러를 하기 식(4)의 화합물과 커플링 반응시켜 하기 식(I)의 오렌지색 분산 염료를 제조하는 것을 특징으로 한다: The method for preparing an orange disperse dye of the present invention is characterized by preparing an orange disperse dye of formula (I) by coupling a coupler of formula (2) with a compound of formula (4):

Figure 112017130975760-pat00001
Figure 112017130975760-pat00001

상기 식에서, X1,X2는 알킬 또는 할로겐이고, A는 산의 잔기, nT는 알킬렌카보네이트, 또는 알킬할라이드인 T로부터 유도된 치환기이고 n은 반복단위이다. Wherein X 1, X 2 is alkyl or halogen, A is a residue derived from T, nT is an alkylene carbonate, or alkyl halide, and n is a repeating unit.

본 발명의 제조방법은 간단하며, 경제적이고 수율이 우수하다. The production method of the present invention is simple, economical and excellent in yield.

도1은 본 발명에 의해 제조된 커플러와 원료 니트로 아닐린 유도체 및 합성된 염료의 HPLC 분석 결과를 나타낸 도면.
도2는 본 발명의 염료에 의해 염색된 결과를 사진으로 촬영한 것을 나타낸 도면.1 is a view showing the results of HPLC analysis of the coupler and the raw material nitro aniline derivatives prepared by the present invention and the synthesized dyes.
Figure 2 is a view showing photographing the results dyed with the dye of the present invention.

이하 본 발명을 상세하게 설명한다. Hereinafter, the present invention will be described in detail.

본 발명의 오렌지색 분산 염료의 제조방법은 다음과 같이 요약된다. The preparation method of the orange disperse dye of the present invention is summarized as follows.

Figure 112017130975760-pat00002
Figure 112017130975760-pat00002

상기 식에서, X1,X2는 알킬 또는 할로겐이고, T는 알킬렌카보네이트, 또는 알킬할라이드이며,nT는 T로부터유도된 치환기이고 n은 반복단위이다. A는 산의 잔기이다. Wherein X 1, X 2 is alkyl or halogen, T is alkylene carbonate, or alkyl halide, n T is a substituent derived from T and n is a repeating unit. A is a residue of an acid.

식(2)의 커플러는 염기 존재하에 식(1)의 9H-카르바졸을 알킬렌카보네이트, 또는 알킬할라이드와 반응시켜 제조된다. 반응은 예를 들어 DMF와 같은 환류 용매하에서 환류시키면서 진행한다. The coupler of formula (2) is prepared by reacting 9H-carbazole of formula (1) with an alkylene carbonate or an alkyl halide in the presence of a base. The reaction proceeds under reflux under a reflux solvent such as, for example, DMF.

식(4)의 화합물은 식(3)의 화합물을 산과 니트로실술포닐산으로 반응시켜 제조한다. 이 반응은 30℃가 넘지 않도록 유지하면서 진행한다. The compound of formula (4) is prepared by reacting the compound of formula (3) with acid and nitrosylsulfonyl acid. This reaction proceeds while maintaining not to exceed 30 degreeC.

식(2)의 커플러와 식(4)의 화합물의 커플링 반응은 용매 존재하에 30℃가 넘지 않도록 유지하면서 진행한다. 여기에 사용되는 용매로는 아세트산, 인산, 알코올, 물 또는 이들의 혼합용매를 들 수 있다. The coupling reaction between the coupler of formula (2) and the compound of formula (4) proceeds while maintaining the solvent not to exceed 30 ° C. As a solvent used here, acetic acid, phosphoric acid, alcohol, water, or a mixed solvent thereof is mentioned.

이하 실시 예를 통해 본 발명을 보다 상세하게 설명하나, 본 발명을 이에 한정하는 것은 아니다. Hereinafter, the present invention will be described in more detail with reference to the following Examples, but the present invention is not limited thereto.

실시 예 1A 커플러 A의 합성 Example 1 Synthesis of Coupler A

Figure 112017130975760-pat00003
Figure 112017130975760-pat00003

500ml 4-구 둥근 바닥 플라스크에 H-Carba(9H-카르바졸) 26g과 EC(Ethylene carbonate) 27.3g, KOH 4.4g, DMF 80g 넣고 약 10분간 교반하여 분산시킨다. 이후 환류될 때까지 승온하여 해당온도에서 약 2시간 정도 반응을 진행한다. 반응이 완료되었으면 상온냉각하고 2L 비커에 옮긴 후 소금 수용액을 투입하여 입자화 될 때까지 수 시간 교반한다. 입자가 발생한 원액을 여과하여 물로 세척하고 탈리한 후 건조한다. 35.9g의 커플러 A 입자를 얻었다. (R1-Carba : 13.1%, R2-Carba : 73.5%, R3-Carba : 13.4%)In a 500 ml four-necked round bottom flask, 26 g of H-Carba (9H-carbazole), 27.3 g of EC (Ethylene carbonate), 4.4 g of KOH, and 80 g of DMF were stirred and dispersed for about 10 minutes. After heating up to reflux, the reaction proceeds for about 2 hours at the temperature. After the reaction was completed, the mixture was cooled to room temperature, transferred to a 2L beaker, and stirred for several hours until an aqueous salt solution was added and granulated. Filtrate generated particles are washed with water, desorbed and dried. 35.9 g of Coupler A particles were obtained. (R 1 -Carba: 13.1%, R 2 -Carba: 73.5%, R 3 -Carba: 13.4%)

실시예 1B 오렌지색 분산 염료 1(Disperse Orange dye 1)의 제조 Example 1B Preparation of Disperse Orange Dye 1

Figure 112017130975760-pat00004
Figure 112017130975760-pat00004

500ml 4-구 둥근 바닥 플라스크에 황산 91.9g을 상온에서 투입한다. 30℃가 넘지 않게 유지하면서 NSA(니트로실술포닐 산) 56.5g을 천천히 넣는다. 이후 DCPNA(2,6-디클로로-p-니트로아닐린) 36g을 30℃ 이하를 유지하면서 분할 투입한 후 2Hr이상 교반한다. 커플링 반응 전 디아조 반응의 완료를 확인한다. 3L 비이커에 물 275g과 AG(아세트산) 128g을 투입한 후 0℃로 냉각한다. 앞에서 합성한 디아조 화합물 용액을 적가한다. 온도를 유지하기 위해 ICE를 일부 추가한다. 이전에 합성한 커플러 A 32.8g을 메탄올 250g에 용해한 후 디아조 화합물이 용해된 3L 비이커에 15~20℃를 유지하며 약 5시간 적가한다. 8시간 이상 유지하면서 교반 후 80~85℃로 승온하여 1시간 유지한다. 온도를 냉각하여 여과하고 뜨거운 물로 세척한 후 건조한다. 60.7g의 붉은 갈색의 Disperse Orange dye 1의 입자를 얻었다.Into a 500 ml four-necked round bottom flask was added 91.9 g of sulfuric acid at room temperature. Slowly add 56.5 g of NSA (nitrosilsulfonyl acid) while keeping it no higher than 30 ° C. Thereafter, 36 g of DCPNA (2,6-dichloro-p-nitroaniline) was dividedly added while maintaining the temperature of 30 ° C. or lower, followed by stirring for 2 Hr or more. Confirm the completion of the diazo reaction before the coupling reaction. 275 g of water and 128 g of AG (acetic acid) were added to a 3 L beaker and cooled to 0 ° C. The diazo compound solution synthesized above is added dropwise. Add some ICE to maintain the temperature. After dissolving 32.8 g of the previously synthesized coupler A in 250 g of methanol, the mixture is added dropwise to a 3L beaker in which the diazo compound is dissolved, and maintained at 15-20 ° C. for about 5 hours. After stirring for 8 hours or more, the temperature was raised to 80-85 ° C. and maintained for 1 hour. Cool the temperature, filter, wash with hot water and dry. 60.7 g of reddish brown disperse orange dye 1 particles were obtained.

실시 예 1A에서 합성된 커플러와, 상기 원료로 사용된 2,6-디클로로-p-니트로아닐린, 그리고 합성된 Disperse Orange dye 1의 HPLC 분석 결과를 도 1에 도시하였다. The HPLC analysis of the coupler synthesized in Example 1A, 2,6-dichloro-p-nitroaniline, and the synthesized Disperse Orange dye 1 used as the raw material is shown in FIG. 1.

또한, 이 염료를 사용하여 염색한 결과 사진을 도 2에 게시하였다. Moreover, the result of dyeing using this dye was shown in FIG.

실시 예 2A 커플러 B의 합성 Example 2 Synthesis of Coupler B

Figure 112017130975760-pat00005
Figure 112017130975760-pat00005

500ml 4-구 둥근 바닥 플라스크에 H-Carba(9H-카르바졸) 26g과 PC(프로필렌 카보네이트) 31.6g, NaOH 2.7g, DMF 80g 넣고 약 10분간 교반하여 분산시킨다. 이 후 환류될 때까지 승온하여 해당온도에서 약 2시간 가량 반응을 진행한다. 반응이 완료 되었으면 상온냉각하고 2L 비이커에 옮긴 후 소금수용액을 투입하여 입자화 될 때까지 수 시간 교반한다. 입자가 발생한 원액을 여과하여 물로 세척하고 탈리한 후 건조한다. 35.2g의 커플러 B 입자를 얻었다. (R1-Carba : 14.4%, R2-Carba : 74.3%, R3-Carba : 11.3%)In a 500 ml four-necked round bottom flask, 26 g of H-Carba (9H-carbazole), 31.6 g of PC (propylene carbonate), 2.7 g of NaOH, and 80 g of DMF were stirred and dispersed for about 10 minutes. After that, the temperature is raised to reflux and the reaction is performed for about 2 hours at the temperature. After the reaction is completed, cool it to room temperature, transfer it to a 2L beaker, add salt aqueous solution, and stir for several hours until it is granulated. Filtrate generated particles are washed with water, desorbed and dried. 35.2 g of coupler B particles were obtained. (R 1 -Carba: 14.4%, R 2 -Carba: 74.3%, R 3 -Carba: 11.3%)

실시예 1B 오렌지색 분산 염료 2(Disperse Orange dye 2)의 제조 Example 1B Preparation of Disperse Orange Dye 2

Figure 112017130975760-pat00006
Figure 112017130975760-pat00006

500ml 4-neck 둥근 바닥 플라스크에 인산 90g을 상온에서 투입한 후 황산 9g을 서서히 적가한다. 30℃가 넘지 않게 유지하면서 NSA(Nitrosylsufonyl acid) 56.5g을 천천히 넣는다. 이후 BMPNA 40g을 30℃이하를 유지하면서 분할 투입한 후 2시간 이상 교반한다. 커플링 반응 전 디아조 반응의 완료를 확인한다. 3L 비이커에 물 275g과 AG(acetic acid) 128g을 투입한 후 0℃로 냉각한다. 앞에서 합성한 디아조 화합물 용액을 적가한다. 온도를 유지하기 위해 얼음을 일부 추가한다. 이전에 합성한 커플러 B 34.6g을 메탄올 250g에 용해한 후 디아조 화합물이 용해된 3L 비이커에 15~20℃를 유지하며 약 5시간 적가한다. 8시간 이상 유지하면서 교반 후 80~85℃로 승온하여 1시간 유지한다. 온도를 냉각하여 여과하고 뜨거운 물로 세척한 후 건조한다. 66.5g의 붉은 갈색의 Disperse Orange dye 2의 입자를 얻었다. Into a 500 ml 4-neck round bottom flask, 90 g of phosphoric acid was added at room temperature, and 9 g of sulfuric acid was slowly added dropwise. Slowly add 56.5 g of NSA (Nitrosylsufonyl acid) while keeping it no higher than 30 ° C. Thereafter, 40 g of BMPNA was dividedly added while maintaining the temperature of 30 ° C. or lower, and then stirred for 2 hours or more. Confirm the completion of the diazo reaction before the coupling reaction. 275g of water and 128g of AG (acetic acid) are added to a 3L beaker and cooled to 0 ℃. The diazo compound solution synthesized above is added dropwise. Add some ice to maintain the temperature. After dissolving 34.6 g of the previously synthesized coupler B in 250 g of methanol, the mixture is added dropwise to a 3L beaker in which the diazo compound is dissolved and maintained at 15 to 20 ° C. for about 5 hours. After stirring for 8 hours or more, the temperature was raised to 80-85 ° C. and maintained for 1 hour. Cool the temperature, filter, wash with hot water and dry. 66.5 g of reddish brown disperse orange dye 2 particles were obtained.

Claims (7)

하기 식(2)의 커플러를 하기 식(4)의 화합물과 커플링 반응시켜 하기 식(I)의 오렌지색 분산 염료를 제조하는 방법:
Figure 112020500140422-pat00007

상기 식에서, X1, X2는 알킬 또는 할로겐이고, A는 산의 잔기, nT는 알킬렌카보네이트인 T로부터 유도된 치환기이고 n은 반목단위이다. A method of preparing an orange disperse dye of formula (I) by coupling a coupler of formula (2) with a compound of formula (4):
Figure 112020500140422-pat00007

Wherein X 1 and X 2 are alkyl or halogen, A is a residue of an acid, nT is a substituent derived from T, which is an alkylene carbonate, and n is a semi-arc unit. 제1항에 있어서, 상기 반응은 30℃ 이하로 유지하면서 수행되는 것을 특징으로 하는 방법. The method of claim 1, wherein the reaction is carried out while maintaining at 30 ℃ or less. 제1항에 있어서, 상기 반응에 사용되는 용매는 아세트산, 인산, 알코올, 물 또는 이들의 혼합물인 것을 특징으로 하는 방법. The method of claim 1 wherein the solvent used in the reaction is acetic acid, phosphoric acid, alcohol, water or mixtures thereof. 제1항에 있어서, 상기 식(2)의 커플러는 염기 존재하에 하기 식(1)의 9H-카르바졸을 알킬렌카보네이트와 반응시켜 제조되는 것을 특징으로 하는 제조 방법:
Figure 112019050278310-pat00008
The process according to claim 1, wherein the coupler of formula (2) is prepared by reacting 9H-carbazole of formula (1) with alkylene carbonate in the presence of a base:
Figure 112019050278310-pat00008
 제4항에 있어서, 상기 커플러를 제조하는 반응은 용매의 환류하에서 수행되는 것을 특징으로 하는 제조방법. The method of claim 4, wherein the reaction for producing the coupler is performed under reflux of a solvent. 제1항에 있어서, 상기 식(4)의 화합물은 하기 식(3)의 화합물을 산, 니트로실술포닐산과 반응시켜 제조하는 것을 특징으로 하는 제조방법:
Figure 112017130975760-pat00009
The method of claim 1, wherein the compound of formula (4) is prepared by reacting a compound of formula (3) with an acid and nitrosyl sulfonyl acid:
Figure 112017130975760-pat00009
 제6항에 있어서, 상기 산은 황산인 것을 특징으로 하는 제조방법.

The method of claim 6, wherein the acid is sulfuric acid.

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