KR102137478B1 - Brilliant blue azo dye and method of preparation thereof, and its use - Google Patents

Brilliant blue azo dye and method of preparation thereof, and its use Download PDF

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KR102137478B1
KR102137478B1 KR1020180016342A KR20180016342A KR102137478B1 KR 102137478 B1 KR102137478 B1 KR 102137478B1 KR 1020180016342 A KR1020180016342 A KR 1020180016342A KR 20180016342 A KR20180016342 A KR 20180016342A KR 102137478 B1 KR102137478 B1 KR 102137478B1
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brilliant blue
blue azo
azo dye
dye
dyeing
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KR1020180016342A
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KR20180021022A (en
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배이춘 리
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항저우 프라리언트 컴퍼니., 리미티드
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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
    • C09B51/00—Nitro or nitroso dyes
    • 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
    • C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
    • 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
    • C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
    • C09B29/0834—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -O-
    • 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
    • C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
    • C09B29/0836—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -N=
    • C09B29/0838—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -N= specific alkyl-CO-N-, aralkyl CON-, cycloalkyl CON-, alkyl OCON-
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D06P1/18—Azo dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D06P1/19—Nitro dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/56—Preparing azo dyes on the material

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

본 발명은 브릴리언트 블루 아조염료 및 이 제조방법과 응용을 개시하는 바, 구조식 식(Ⅰ)에 도시된 바와 같이 본 발명은 브릴리언트 블루 아조염료가 폴리에스터 섬유의 염색 또는 프린팅에서의 응용을 개시한다. 브릴리언트 블루 아조염료를 구조통식(Ⅰ)에서 선택된 적어도 한 화합물과 혼합하여 분산염료 조성물을 제작하되 상기 분산염료 조성물은 폴리에스터 섬유의 염색 또는 프린팅에 응용될 수 있다. 본 발명은 염색을 진행할 경우 내세척 견뢰도, 내마찰 견뢰도, 땀 견뢰도, 내일광 견뢰도 및 염색율이 모두 훌륭하고 본 발명의 분산염료 조성물의 염색강도가 높으며 색상이 화려하고 염색성능이 우수한 바, 특히 우수한 워싱 견뢰도를 가지고 색상이 안정되며 쉽게 퇴색되지 않고 원가가 비교적 낮다.The present invention discloses a brilliant blue azo dye and its manufacturing method and application. As shown in structural formula (I), the present invention discloses an application of a brilliant blue azo dye in dyeing or printing of polyester fibers. A dispersion dye composition is prepared by mixing the brilliant blue azo dye with at least one compound selected from structural formula (I), wherein the dispersion dye composition can be applied to dyeing or printing of polyester fibers. The present invention is excellent in both fastness to wash, friction fastness, sweat fastness, light fastness to tomorrow, and dyeing rate when dyeing is progressed. The color is stable with wash fastness, does not fade easily, and the cost is relatively low.

Description

브릴리언트 블루 아조염료 및 이 제조방법과 응용{Brilliant blue azo dye and method of preparation thereof, and its use}Brilliant blue azo dye and method of preparation thereof, and its use

본 발명은 염료기술분야에 관한 것으로서 구체적으로 브릴리언트 블루 아조염료 및 이 제조방법과 응용에 관한 것이다.The present invention relates to the field of dye technology, and specifically, to a brilliant blue azo dye and its manufacturing method and application.

21세기에 들어선 후 세계방직시장의 경쟁은 더욱더 치열해졌고 동남아의 경제는 이미 낮은 원가, 높은 성장의 대명사가 되었으며 유럽, 미국 등의 방직공업업무도 빠른 속도로 아세아로 이동하고 있다. 방직품시장의 치열한 경쟁의 형세에 적응하기 위하여 방직품의 생산원가를 끊임없이 하락시키고 제품질량을 끊임없이 향상시키며 환경부하를 끊임없이 감소시키는 것은 이미 방직기업들의 공동한 목표가 되었다.Since entering the 21st century, competition in the global textile market has become more and more intense, the economy in Southeast Asia has already become synonymous with low cost and high growth, and the textile industry in Europe and the United States is rapidly moving to Asia. In order to adapt to the fierce competition in the textile market, it has already become a common goal of textile companies to continuously decrease the production cost of textile products, continuously improve product mass, and continuously reduce the environmental load.

분산염료는 물에서의 용해도가 아주 낮고 과립이 아주 가늘며 염료액에서 분산체를 형성하므로 비이온형 염료에 속하는 바, 폴리에스터의 염색에 주요하게 사용되고 염색 견뢰도가 비교적 높다.Disperse dyes have a very low solubility in water, very fine granules, and form a dispersion in a dye solution, so they belong to non-ionic dyes, and are mainly used for dyeing polyesters and have relatively high color fastness.

아조염료(아조기 양단이 아릴기에 연결된 일종의 유기 화합물)는 방직품 의류가 날염 공법에서 응용이 가장 광범위한 일종의 합성염료로서 여러가지 천연섬유와 합성섬유의 염색 및 프린팅에 사용되고 또 페인트, 플라스틱, 고무 등의 착색에도 사용된다. 아조염료는 빨간색, 노란색, 녹색, 파란색 등과 같은 여러가지 색이 있는데 기존의 파란색 아조염료는 워싱 견뢰도가 낮은 문제가 존재하였고 고온조건에서 직물섬유 내부로부터 아주 쉽게 이전되어 직물에 대한 염료의 염색 견뢰도에 엄중한 영향을 미쳤다.Azo dyes (a type of organic compound with both ends of azo groups connected to an aryl group) are a kind of synthetic dyes in which textile garments are most widely applied in the printing method, used for dyeing and printing of various natural fibers and synthetic fibers, and also for coloring of paint, plastic, rubber, etc. Is used. Azo dyes have various colors such as red, yellow, green, and blue. The existing blue azo dyes have a problem of low wash fastness and are very easily transferred from the inside of the fabric fibers under high temperature conditions, and are very strict with the dye fastness of dyes to the fabric. Had one effect.

본 발명이 해결하고자 하는 기술적 과제는 비교적 우수한 염색 견뢰도를 갖는 브릴리언트 블루 아조염료를 제공하는 것이다.The technical problem to be solved by the present invention is to provide a brilliant blue azo dye having a relatively good color fastness.

상술한 기술적 과제를 해결하기 위하여 본 발명의 기술적 해결수단은 다음과 같다.In order to solve the above technical problem, the technical solution of the present invention is as follows.

구조식 식(Ⅰ)에 도시된 바와 같은 브릴리언트 블루 아조염료:Brilliant blue azo dye as shown in structural formula (I):

Figure 112018014568434-pat00001
(Ⅰ);
Figure 112018014568434-pat00001
(I);

여기서 R1은 H, CH3O 또는 C2H5O를 나타내고;Where R 1 represents H, CH 3 O or C 2 H 5 O;

R2는 C1~C4알킬렌를 나타내며;R 2 represents C 1 -C 4 alkylene;

R3은 C1~C4알킬기를 나타낸다.R 3 represents a C 1 to C 4 alkyl group.

바람직한 것으로서 R1은 CH3O를 나타낸다.As preferred, R 1 represents CH 3 O.

바람직한 것으로서 R2는 에틸렌을 나타낸다.As preferred, R 2 represents ethylene.

바람직한 것으로서 R3은 메틸을 나타낸다.As preferred, R 3 represents methyl.

바람직한 것으로서 다음과 같은 단계를 포함한다.The preferred steps include the following steps.

1) 6-브롬-2,4-디니트로아닐린은 니트로실황산을 사용하여 다이아조화를 진행한 다음 커플링성분과 커플링반응을 진행하고 여과, 워싱, 건조를 거쳐 식(1)에 도시된 구조식을 얻는 단계:1) 6-bromine-2,4-dinitroaniline was subjected to diazoization using nitrosylsulfuric acid, followed by a coupling reaction with a coupling component, filtered, washed, and dried, as shown in equation (1). Steps to get structural formula:

Figure 112018014568434-pat00002
(1),
Figure 112018014568434-pat00002
(One),

여기서 R1은 H, CH3O 또는 C2H5O를 나타내고 R2는 C1~C4알킬렌을 나타내며 R3은 C1~C4알킬기를 나타내고;Wherein R 1 represents H, CH 3 O or C 2 H 5 O, R 2 represents C 1 to C 4 alkylene and R 3 represents a C 1 to C 4 alkyl group;

상기 커플링성분은 식(2)에 도시된 구조식:The coupling component is a structural formula shown in equation (2):

Figure 112018014568434-pat00003
(2),
Figure 112018014568434-pat00003
(2),

여기서 R1은 H, CH3O 또는 C2H5O를 나타내고 R2는 C1~C4알킬렌을 나타내며 R3은 C1~C4알킬기를 나타냄;Wherein R 1 represents H, CH 3 O or C 2 H 5 O, R 2 represents C 1 to C 4 alkylene and R 3 represents a C 1 to C 4 alkyl group;

2) 식(1)을 디메틸아세트아미드에서 아연염과 구리염을 사용하여 시안화반응을 진행하고 조품을 여과해내는 단계; 2) formula (1) in dimethylacetamide using a zinc salt and a copper salt to undergo a cyanation reaction and filtering the crude product;

3) 조품을 물에서 산성 염화철로 소독하고 여과, 워싱하여 브릴리언트 블루 아조염료를 얻는 단계.3) Step of sterilizing the crude water with acidic iron chloride, filtering and washing to obtain brilliant blue azo dye.

본 발명은 상기 브릴리언트 블루 아조염료를 포함하는 분산염료를 더 제공하는데 상기 브릴리언트 블루 아조염료는 구조통식(Ⅰ)에서 선택된 적어도 한 화합물이다.The present invention further provides a disperse dye comprising the brilliant blue azo dye, wherein the brilliant blue azo dye is at least one compound selected from structural formula (I).

설명해야 할 것은 염료업체의 특수성으로 인하여 각 성분은 순정품으로 만들기 힘들 뿐만 아니라 그러할 필요도 없으며 소량의 수분 및 미량의 물리적 불순물을 포함하게 되는데 이러한 수분과 물리적 불순물의 존재는 본 발명에서 받아들일 수 있는 범위내에 있다.It should be explained that due to the specificity of the dye company, each component is not only difficult to make into a genuine product, but also need not be, and contains a small amount of moisture and a small amount of physical impurities. The presence of such moisture and physical impurities is acceptable in the present invention. It is within range.

본 발명의 염료 조성물은 본 업체들이 통상적으로 사용하는 제조방법에 의해 얻을 수 있는데 예를 들면 각 성분들을 기 설정된 배분율에 따라 혼합한 후 보조제(분산제, 물 또는 기타 습윤제 등을 포함)의 존재하에 샌드 밀 또는 그라인더 등 분쇄장치를 이용하여 미립자화를 진행함으로써 상기 분산염료 조성물을 얻을 수 있고, 또 각 성분을 보조제, 물 또는 기타 습윤제의 존재하에 각각 샌드 밀 또는 그라인더 등 분쇄장치를 이용하여 미립자화를 진행한 후 기 설정된 배분율에 따라 혼합함으로써 상기 분산 흑색 열묘 혼합물을 얻을 수도 있다.The dye composition of the present invention can be obtained by a manufacturing method commonly used by the present companies, for example, after mixing each component according to a predetermined distribution ratio, sand in the presence of an auxiliary agent (including a dispersant, water or other wetting agent, etc.) The dispersion dye composition can be obtained by performing micronization using a grinding device such as a mill or a grinder, and each component is micronized using a grinding device such as a sand mill or a grinder, respectively, in the presence of an auxiliary agent, water or other wetting agent. After proceeding, it is also possible to obtain the dispersed black hot seedling mixture by mixing according to a predetermined distribution ratio.

본 발명은 상기 브릴리언트 블루 아조염료가 폴리에스터 섬유의 염색 또는 프린팅에서의 응용을 더 제공한다.The present invention further provides the application of the brilliant blue azo dye in dyeing or printing of polyester fibers.

본 발명은 상기 분산염료 조성물가 폴리에스터 섬유의 염색 또는 프린팅에서의 응용을 더 제공한다.The present invention further provides an application in which the dispersion dye composition is dyed or printed on polyester fibers.

본 발명은 상기 브릴리언트 블루 아조염료를 이용하여 염색 또는 프린팅을 진행하는 폴리에스터 섬유재료를 더 제공한다.The present invention further provides a polyester fiber material for dyeing or printing using the brilliant blue azo dye.

본 발명은 상기 분산염료를 이용하여 염색 또는 프린팅을 진행하는 폴리에스터 섬유재료를 더 제공한다.The present invention further provides a polyester fiber material that undergoes dyeing or printing using the dispersion dye.

선행기술과 비교하면 본 발명의 유리한 효과는 다음과 같다.Advantageous effects of the present invention as compared to the prior art are as follows.

본 발명은 염색을 진행할 경우 내세척 견뢰도, 내마찰 견뢰도, 땀 견뢰도, 내일광 견뢰도 및 염색율이 모두 훌륭하고 본 발명의 분산염료 조성물의 염색강도가 높으며 색상이 화려하고 염색성능이 우수한 바, 특히 우수한 워싱 견뢰도를 가지고 색상이 안정되며 쉽게 퇴색되지 않고 원가가 비교적 낮다.The present invention is excellent in both wash fastness, friction fastness, sweat fastness, light fastness to tomorrow, and dyeing rate when dyeing, the color of the dispersion dye composition of the present invention is high, the color is colorful, and the dyeing performance is excellent. The color is stable with wash fastness, does not fade easily, and the cost is relatively low.

실시예1Example 1

본 실시예는 브릴리언트 블루 아조염료인 바, 구조식은 다음과 같다:This example is a brilliant blue azo dye, and the structural formula is as follows:

Figure 112018014568434-pat00004
Figure 112018014568434-pat00004

여기서 R1은 H를 나타내고;Where R 1 represents H;

R2는 메틸렌을 나타내며;R 2 represents methylene;

R3은 에틸을 나타낸다.R 3 represents ethyl.

상기 브릴리언트 블루 아조염료의 제조방법은 다음과 같다.The method for preparing the brilliant blue azo dye is as follows.

1) 디아조 주전자에 일정한 양의 황산과 니트로실황산을 추가하고 온도를 20~25도 사이로 제어하며 6-브롬-2,4-디니트로아닐린을 천천히 추가한 다음 20~25도에서 4시간동안 보온반응을 진행하고 얼음물로 라스트 포인트를 검출하며 합격된 후 예비용으로 준비한다.1) Add a certain amount of sulfuric acid and nitrosylsulfuric acid to the diazo kettle, control the temperature between 20 and 25 degrees, slowly add 6-bromine-2,4-dinitroaniline, and then 4 hours at 20 to 25 degrees. The warming reaction is performed, the last point is detected with ice water, and after passing, it is prepared for preliminary use.

2) 커플링통에 물, 황산 및 술팜산을 추가한 후 커플링성분(3-N,N-디프로피오닐 옥시메틸 - 아세트 아닐리드)을 천천히 추가하여 용해하는데 용해가 완전히 진행되면 얼음을 추가하여 온도를 0도좌우로 내리고 상기 준비된 디아조늄염을 천천히 추가하여 커플링반응을 진행하며 디아조늄염을 추가 완료한 다음 디아조늄염이 라스트 포인트로 소실될 때까지 계속하여 교반하고 증기를 통과시켜 55~60도까지 승온시키며 1시간동안 보온 결정화시고 중성이 될 때까지 50도의 뜨거운 물로 필터 케이트를 여과 세척하고 방출, 건조하여 아래 구조식을 얻는다.2) After adding water, sulfuric acid, and sulfamic acid to the coupling container, slowly dissolve the coupling component (3-N,N-dipropionyl oxymethyl-acetanilide). To 0 degrees left and right, the prepared diazonium salt is slowly added to proceed the coupling reaction, the diazonium salt is further added, and stirring is continued until the diazonium salt disappears to the last point and the steam is passed through 55~ Heated to 60°C, crystallized for 1 hour to keep warm, filtered and washed with filter water with hot water at 50°C until neutral, discharged and dried to obtain the following structural formula.

Figure 112018014568434-pat00005
Figure 112018014568434-pat00005

여기서 R1은 H를 나타내고 R2는 메틸렌을 나타내며 R3은 에틸을 나타낸다.Where R 1 represents H, R 2 represents methylene and R 3 represents ethyl.

3) 시안화 주전자에 디메틸아세트아미드를 추가하고 상기 구조식을 투입하여 90~95까지 승온시킨 다음 용해하고 80도 좌우까지 냉각시켜 아연염과 구리염을 추가한 다음 온도를 85~90도로 유지시켜 1시간동안 반응시킨 후 샘플링하여 라스트 포인트를 검출하는데 합격된 후 20~40도로 냉각시키고 천천히 물을 추가한 다음 여과시켜 조품을 얻는다.3) Add dimethylacetamide to the cyanide kettle, add the above structural formula, heat up to 90-95, dissolve, cool to 80 degrees left and right, add zinc salt and copper salt, and keep the temperature at 85-90 degrees for 1 hour After reacting for a while, sampling was passed to detect the last point, cooled to 20-40 degrees, slowly added water, and filtered to obtain a crude product.

4) 소독 주전자에 물을 추가하고 조품을 투입한 다음 펄프를 균일하게 반죽하고 산성 염화철용액을 추가한 후 60~65도로 승온시켜 2시간동안 반응한 다음 여과, 워싱하여 상기 브릴리언트 블루 아조염료를 얻는다.4) Add water to the disinfection kettle, add the product, knead the pulp uniformly, add an acidic iron chloride solution, warm it up to 60~65 degrees, react for 2 hours, then filter and wash to obtain the brilliant blue azo dye .

실시예2Example 2

본 실시예는 브릴리언트 블루 아조염료인 바, 구조식은 다음과 같다.This example is a brilliant blue azo dye, and the structural formula is as follows.

Figure 112018014568434-pat00006
Figure 112018014568434-pat00006

여기서 R1은 CH3O를 나타내고;Where R 1 represents CH 3 O;

R2는 에틸렌을 나타내며;R 2 represents ethylene;

R3은 메틸을 나타낸다.R 3 represents methyl.

상기 브릴리언트 블루 아조염료의 제조방법은 실시예1를 참조 바라는데 상이한 점은 커플링성분이 상이한 것이다.The method for preparing the brilliant blue azo dye is referred to Example 1, but the difference is that the coupling components are different.

실시예3Example 3

본 실시예는 브릴리언트 블루 아조염료인 바, 구조식은 다음과 같다.This example is a brilliant blue azo dye, and the structural formula is as follows.

Figure 112018014568434-pat00007
Figure 112018014568434-pat00007

여기서 R1은 C2H5O를 나타내고;Where R 1 represents C 2 H 5 O;

R2는 부틸렌을 나타내며;R 2 represents butylene;

R3은 에틸을 나타낸다.R 3 represents ethyl.

상기 브릴리언트 블루 아조염료의 제조방법은 실시예1을 참조 바라는데 상이한 점은 커플링성분이 상이한 것이다.The method for preparing the brilliant blue azo dye is referred to Example 1, but the difference is that the coupling components are different.

실시예4Example 4

본 실시예는 브릴리언트 블루 아조염료인 바, 구조식은 다음과 같다.This example is a brilliant blue azo dye, and the structural formula is as follows.

Figure 112018014568434-pat00008
Figure 112018014568434-pat00008

여기서 R1은 CH3O를 나타내고;Where R 1 represents CH 3 O;

R2는 에틸렌을 나타내며;R 2 represents ethylene;

R3은 프로필기를 나타낸다.R 3 represents a propyl group.

상기 브릴리언트 블루 아조염료의 제조방법은 실시예1을 참조 바라는데 상이한 점은 커플링성분이 상이한 것이다.The method for preparing the brilliant blue azo dye is referred to Example 1, but the difference is that the coupling components are different.

실시예5Example 5

본 실시예는 브릴리언트 블루 아조염료인 바, 구조식은 다음과 같다.This example is a brilliant blue azo dye, and the structural formula is as follows.

Figure 112018014568434-pat00009
Figure 112018014568434-pat00009

여기서 R1은 C2H5O를 나타내고;Where R 1 represents C 2 H 5 O;

R2는 메틸렌을 나타내며; R 2 represents methylene;

R3은 부틸을 나타낸다.R 3 represents butyl.

상기 브릴리언트 블루 아조염료의 제조방법은 실시예1을 참조 바라는데 상이한 점은 커플링성분이 상이한 것이다.The method for preparing the brilliant blue azo dye is referred to Example 1, but the difference is that the coupling components are different.

검출예1Detection example 1

실시예1~5에서 제작하여 얻은 분산 흑색 염료 혼합물을 각각 취하고500mL의 물에 분산시켜 분산액을 얻은 다음 20mL의 분산액과 60mL의 물을 혼합하여 염료액을 얻으며 초산으로 염욕의 pH를 5로 조절한 다음 70℃까지 승온하고 4g의 폴리에스터 섬유를 넣어 염색을 진행함과 동시에 30min내에 염욕온도를 70℃에서 130℃까지 승온시키고 130℃ 조건하에서 30min을 보온한 다음 90℃까지 냉각시키고 샘플링한다. 샘플 천의 색을 관찰하고 국제표준인 GB/T3921-1997, GB/T3920-1997, GB/T3922-1997, GB/T8427-1998을 사용하여 샘플 천의 워셔블 견뢰도, 내마찰 견뢰도, 땀 견뢰도 및 내일광 견뢰도를 각각 테스트하며 GB/T9337-2009방법을 사용하여 염료염색율을 테스트하는데 테스트결과는 표 1을 참조하기 바란다.Each of the dispersion black dye mixtures prepared in Examples 1 to 5 was taken and dispersed in 500 mL of water to obtain a dispersion, followed by mixing 20 mL of dispersion and 60 mL of water to obtain a dye solution, and adjusting the pH of the salt bath with acetic acid to 5 Then, the temperature was raised to 70° C., and 4 g of polyester fiber was added to the dyeing process. At the same time, the salt bath temperature was raised from 70° C. to 130° C. in 30 min., and 30 min. Observe the color of the sample cloth and use the international standards GB/T3921-1997, GB/T3920-1997, GB/T3922-1997, GB/T8427-1998 for washable, anti-friction fastness, sweat fastness and tomorrow Light fastness is tested individually and dye dyeing rate is tested using the GB/T9337-2009 method. See Table 1 for test results.

[표 1][Table 1]

Figure 112018014568434-pat00010
Figure 112018014568434-pat00010

표 1로부터 알 수 있다 싶이 실시예1~5에서 제조된 염료 조성물의 각 견뢰도성능은 모두 비교적 우수한 바, 여기서 R1가 CH3O를 나타내고 R2가 에틸렌을 나타내며 R3이 메틸을 나타낼 경우 제작된 브릴리언트 블루 아조염료의 염색 견뢰도, 워싱 견뢰도 및 염색율이 제일 우수하다.As can be seen from Table 1, the fastness performances of the dye compositions prepared in Examples 1 to 5 are all relatively good, where R 1 represents CH 3 O, R 2 represents ethylene, and R 3 represents methyl. The produced brilliant blue azo dye has the best dyeing fastness, wash fastness and dyeing rate.

실시예6Example 6

본 실시예는 분산염료로서 실시예1에 도시된 브릴리언트 블루 아조염료, 실시예2에 도시된 브릴리언트 블루 아조염료 및 실시예3에 도시된 브릴리언트 블루 아조염료를 질량비 1:2:2의 비율로 혼합하여 얻는다.In this example, as a disperse dye, the brilliant blue azo dye shown in Example 1, the brilliant blue azo dye shown in Example 2, and the brilliant blue azo dye shown in Example 3 are mixed at a mass ratio of 1:2:2. To get it.

실시예7Example 7

본 실시예는 분산염료로서 실시예2에 도시된 브릴리언트 블루 아조염료와 실시예3에 도시된 브릴리언트 블루 아조염료를 질량비 2:3의 비율로 혼합하여 얻는다.This example is obtained by mixing the brilliant blue azo dye shown in Example 2 and the brilliant blue azo dye shown in Example 3 as a dispersion dye at a ratio of 2:3 by mass.

실시예8Example 8

본 실시예는 분산염료로서 실시예3에 도시된 브릴리언트 블루 아조염료와 실시예4에 도시된 브릴리언트 블루 아조염료를 질량비 3:1의 비율로 혼합하여 얻는다.This example is obtained by mixing the brilliant blue azo dye shown in Example 3 and the brilliant blue azo dye shown in Example 4 as a dispersion dye at a ratio of 3:1 by mass.

실시예9Example 9

본 실시예는 분산염료로서 실시예1에 도시된 브릴리언트 블루 아조염료와 실시예5에 도시된 브릴리언트 블루 아조염료를 질량비 1:3의 비율로 혼합하여 얻는다.This example is obtained by mixing the brilliant blue azo dye shown in Example 1 and the brilliant blue azo dye shown in Example 5 as a dispersion dye at a ratio of 1:3 by mass.

실시예10Example 10

본 실시예는 분산염료로서 실시예1에 도시된 브릴리언트 블루 아조염료, 실시예2에 도시된 브릴리언트 블루 아조염료, 실시예3에 도시된 브릴리언트 블루 아조염료, 실시예4에 도시된 브릴리언트 블루 아조염료와 실시예5에 도시된 브릴리언트 블루 아조염료를 질량비 1:2:4:3:1의 비율로 혼합하여 얻는다.This example is a dispersion dye, a brilliant blue azo dye shown in Example 1, a brilliant blue azo dye shown in Example 2, a brilliant blue azo dye shown in Example 3, and a brilliant blue azo dye shown in Example 4 And the brilliant blue azo dye shown in Example 5 are obtained by mixing in a ratio of 1:2:4:3:1 by mass.

검출예2Detection example 2

실시예6~10에서 제조된 분산염료 1.0g을 취하여 검출예1과 같은 방법을 사용하여 상기 분산염료 조성물로 폴리에스터 섬유 천을 염색함으로써 샘플 천의 내세척 견뢰도, 내마찰 견뢰도, 땀 견뢰도, 내일광 견뢰도 및 염색율을 테스트하는데 테스트결과는 표 2를 참조하기 바란다.By taking 1.0 g of the disperse dye prepared in Examples 6 to 10 and dyeing the polyester fiber cloth with the disperse dye composition using the same method as in Detection Example 1, the wash fastness, anti-friction fastness, sweat fastness, and tomorrow light of the sample cloth are dyed. To test the fastness and staining rate, see Table 2 for test results.

[표 2][Table 2]

Figure 112018014568434-pat00011
Figure 112018014568434-pat00011

표 2로부터 알 수 있다 싶이 실시예6~10에서 제조된 분산염료의 각 견뢰도성능은 모두 비교적 우수한 바, 여기서 실시예6에서 제조된 염료 조성물의 염색 견뢰도, 워싱 견뢰도 및 염색율이 제일 우수하다.As can be seen from Table 2, the fastness performances of the dispersion dyes prepared in Examples 6 to 10 are all relatively excellent, where the dyeing fastness, washing fastness and dyeing rate of the dye composition prepared in Example 6 are the best. .

Claims (10)

구조식 식(Ⅰ)에 도시된 바와 같은 것을 특징으로 하는 브릴리언트 블루 아조염료:
Figure 112019130993560-pat00012
(Ⅰ);
여기서,
R1은 H이고, R2는 메틸렌이고, R3은 에틸이거나;
R1은 C2H5O이고, R2는 부틸렌이고, R3은 에틸이거나;
R1은 CH3O이고, R2는 에틸렌이고, R3은 프로필이거나; 또는
R1은 C2H5O이고, R2는 메틸렌이고, R3은 부틸이다.Brilliant blue azo dye, characterized in that as shown in structural formula (I):
Figure 112019130993560-pat00012
(I);
here,
R 1 is H, R 2 is methylene, and R 3 is ethyl;
R 1 is C 2 H 5 O, R 2 is butylene, and R 3 is ethyl;
R 1 is CH 3 O, R 2 is ethylene, and R 3 is propyl; or
R 1 is C 2 H 5 O, R 2 is methylene, and R 3 is butyl. 삭제delete 삭제delete 삭제delete 제1항의 브릴리언트 블루 아조염료의 제조방법으로서,
1) 6-브롬-2,4-디니트로아닐린은 니트로실황산을 사용하여 다이아조화를 진행한 다음 커플링성분과 커플링반응을 진행하고 여과, 워싱, 건조를 거쳐 식(1)에 도시된 구조식을 얻는 단계:
Figure 112019130993560-pat00013
(1),
여기서, R1은 H이고, R2는 메틸렌이고, R3은 에틸이거나; R1은 C2H5O이고, R2는 부틸렌이고, R3은 에틸이거나; R1은 CH3O이고, R2는 에틸렌이고, R3은 프로필이거나; 또는 R1은 C2H5O이고, R2는 메틸렌이고, R3은 부틸임;
상기 커플링성분은 식(2)에 도시된 구조식:
Figure 112019130993560-pat00014
(2),
여기서, R1은 H이고, R2는 메틸렌이고, R3은 에틸이거나; R1은 C2H5O이고, R2는 부틸렌이고, R3은 에틸이거나; R1은 CH3O이고, R2는 에틸렌이고, R3은 프로필이거나; 또는 R1은 C2H5O이고, R2는 메틸렌이고, R3은 부틸임;
2) 식(1)을 디메틸아세트아미드에서 아연염과 구리염을 사용하여 시안화반응을 진행하고 조품을 여과해내는 단계;
3) 조품을 물에서 산성 염화철로 소독하고 여과, 워싱하여 브릴리언트 블루 아조염료를 얻는 단계를 포함하는 것을 특징으로 하는 브릴리언트 블루 아조염료의 제조방법.A method for producing the brilliant blue azo dye of claim 1,
1) 6-bromine-2,4-dinitroaniline was subjected to diazoization using nitrosylsulfuric acid, followed by a coupling reaction with a coupling component, filtered, washed, and dried, as shown in equation (1). Steps to get structural formula:
Figure 112019130993560-pat00013
(One),
Where R 1 is H, R 2 is methylene, and R 3 is ethyl; R 1 is C 2 H 5 O, R 2 is butylene, and R 3 is ethyl; R 1 is CH 3 O, R 2 is ethylene, and R 3 is propyl; Or R 1 is C 2 H 5 O, R 2 is methylene, and R 3 is butyl;
The coupling component is a structural formula shown in equation (2):
Figure 112019130993560-pat00014
(2),
Where R 1 is H, R 2 is methylene, and R 3 is ethyl; R 1 is C 2 H 5 O, R 2 is butylene, and R 3 is ethyl; R 1 is CH 3 O, R 2 is ethylene, and R 3 is propyl; Or R 1 is C 2 H 5 O, R 2 is methylene, and R 3 is butyl;
2) formula (1) in dimethylacetamide using a zinc salt and a copper salt to undergo a cyanation reaction and filtering the crude product;
3) A method of manufacturing a brilliant blue azo dye comprising disinfecting the crude product in water with acidic iron chloride, filtering and washing to obtain a brilliant blue azo dye. 청구항1의 임의의 브릴리언트 블루 아조염료를 포함하되 상기 브릴리언트 블루 아조염료는 구조식(Ⅰ)에서 선택된 적어도 한 화합물인 것을 특징으로 하는 분산염료.A dispersion dye comprising any of the brilliant blue azo dyes of claim 1, wherein the brilliant blue azo dyes are at least one compound selected from structural formula (I). 삭제delete 삭제delete 청구항1의 임의의 브릴리언트 블루 아조염료를 이용하여 염색 또는 프린팅을 진행하는 폴리에스터 섬유재료.A polyester fiber material for dyeing or printing using any brilliant blue azo dye of claim 1. 청구항6의 분산염료를 이용하여 염색 또는 프린팅을 진행하는 폴리에스터 섬유재료. Polyester fiber material for dyeing or printing using the disperse dye of claim 6.
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