KR101244344B1 - Reactive olive dye having high color regeneration - Google Patents

Reactive olive dye having high color regeneration Download PDF

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KR101244344B1
KR101244344B1 KR1020100124294A KR20100124294A KR101244344B1 KR 101244344 B1 KR101244344 B1 KR 101244344B1 KR 1020100124294 A KR1020100124294 A KR 1020100124294A KR 20100124294 A KR20100124294 A KR 20100124294A KR 101244344 B1 KR101244344 B1 KR 101244344B1
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olive
dye
reactive
formula
reactive dye
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KR20120063214A (en
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정진욱
윤여종
이주현
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오영산업주식회사
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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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/022—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring the heterocyclic ring being alternatively specified
    • C09B62/024—Anthracene 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/207—Dyes with amino groups and with onium groups
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/52—Amino-hydroxy-anthraquinones; Ethers and esters thereof sulfonated
    • 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
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof

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Abstract

본 발명은 하기 화학식 1로 표시되는 올리브색 반응성 염료에 관한 것이다.
본 발명은 올리브색 반응성 염료는 청색 색소 모체와 황색 색소 모체를 한 분자로 결합시킨 단일구조의 염료로서, 배합에 의한 염료로 구현되는 올리브색보다 색상차가 적고, 색재현성이 우수하며, 수세성이 우수하여 습윤견뢰도가 우수하므로, 면반응성 염료로서 유용하다.
화학식 1

Figure 112010080573390-pat00024

(상기 식에서, M, R, X, A 및 n은 명세서에서 정의한 바와 같다.)The present invention relates to an olive reactive dye represented by the following formula (1).
In the present invention, the olive-colored reactive dye is a dye having a single structure in which a blue pigment parent and a yellow pigment parent are combined into one molecule, and have a smaller color difference than the olive color realized by the dye by blending, excellent color reproducibility, and excellent flushing ability. Since it is excellent in wet fastness, it is useful as a cotton reactive dye.
Formula 1
Figure 112010080573390-pat00024

(Wherein M, R, X, A and n are as defined in the specification).

Description

색재현성이 우수한 올리브색 반응성 염료{REACTIVE OLIVE DYE HAVING HIGH COLOR REGENERATION}Olive Reactive Dye with Excellent Color Reproduction {REACTIVE OLIVE DYE HAVING HIGH COLOR REGENERATION}

본 발명은 색재현성이 우수한 올리브색 반응성 염료에 관한 것으로서, 더욱 상세하게는 청색 색소 모체와 황색 색소 모체를 한 분자로 결합시킨 단일구조의 염료로서 색재현성이 우수하며, 수세성이 우수하여 습윤견뢰도가 우수한 올리브색 반응성 염료에 관한 것이다.The present invention relates to an olive-colored reactive dye having excellent color reproducibility. More specifically, the present invention relates to a dye having a single structure in which a blue pigment matrix and a yellow pigment matrix are combined in one molecule, and have excellent color reproducibility and excellent water washability. It relates to an excellent olive reactive dye.

반응성 염료의 색상 표현은 황색, 적색, 청색 염료를 다양한 비율로 배합하여 염색하는 방법이 일반적이다. 현재 보편적으로 사용되고 있는 반응성 3원색 염료로는 하기에 제시된 구조와 같으며, 이러한 3원색 염료는 다양한 색상을 구현하는데 필수적이다.The color representation of the reactive dye is generally a method of dyeing by combining a variety of yellow, red, blue dyes. Reactive trichromatic dyes that are currently commonly used are the same as the structure shown below, these trichromatic dyes are essential to implement a variety of colors.

황색(C. I. Reactive Yellow 145)Yellow (C. I. Reactive Yellow 145)

Figure 112010080573390-pat00001
Figure 112010080573390-pat00001

적색(C. I. Reactive Red 195)Red (C. I. Reactive Red 195)

Figure 112010080573390-pat00002
Figure 112010080573390-pat00002

청색(C. I. Reactive Blue 222)Blue (C. I. Reactive Blue 222)

Figure 112010080573390-pat00003
Figure 112010080573390-pat00003

그러나, 소비자들은 선명한 황색, 선명한 적색, 선명한 청색보다는 중간 색상들, 예를 들면 카키색, 아이보리색, 올리브색, 브라운색과 같이 황색, 적색, 청색이 적당한 비율로 배합된 색상들을 선호한다. However, consumers prefer colors with moderate proportions of medium colors, such as khaki, ivory, olive and brown, rather than bright yellow, bright red and bright blue.

즉, 선명한 3원색을 배합하여 자연 환경에 보다 가까운 색상들을 얻기 위하여 관련염색 업체들은 시장에서 요구하는 색상의 염색작업에 많은 기술과 노력을 집중하고 있다. In other words, in order to obtain the colors closer to the natural environment by combining the vivid three primary colors, related dyeing companies are focusing a lot of technology and efforts on the dyeing of colors required by the market.

그러나 이러한 색상들 중에서는 색 좌표 상에서 원점(절대 흑색)에 가까운 색상들도 있고, 자연 환경에 보다 가까운 중간 색상들을 표현하기 위하여 선명한 3원색인 황색(Reactive Yellow 145), 적색(Reactive Red 195), 청색(Reactive Blue 222)과 같은 염료를 배합할 때, 작은 배합의 차이에서 최종 염료의 색상 차가 커지는 문제가 발생할 수 있다.However, some of these colors are close to the origin (absolute black) in the color coordinates, and the vivid three primary colors yellow (Reactive Yellow 145), red (Reactive Red 195), When blending a dye such as Reactive Blue 222, a small difference in blending may cause a problem that the color difference of the final dye becomes large.

이러한 문제를 극복하고자 대한민국 특허 제699194호에서는 하기 구조의 반응성 염료를 개시하고 있다.In order to overcome this problem, Korean Patent No. 699194 discloses a reactive dye having the following structure.

Figure 112010080573390-pat00004
Figure 112010080573390-pat00004

상기 반응성 염료는 한 분자 내에 청색 색소와 황색 색소를 동시에 보유함으로써, 단일분자로 올리브 색상을 구현하는 특징이 있다. 이에, 상기 선행발명은 청색 염료와 황색 염료 각각을 적절한 혼합비로 배합하여 올리브 색상을 구현하는 경우보다 단일 구조의 염료를 사용함으로써, 염색 작업의 색상 재현성을 높일 수 있다고 밝히고 있다. The reactive dyes are characterized by embodying an olive color with a single molecule by simultaneously holding a blue pigment and a yellow pigment in one molecule. Accordingly, the above-mentioned invention reveals that by using a dye having a single structure than when combining the blue dye and the yellow dye at an appropriate mixing ratio to realize the olive color, the color reproducibility of the dyeing operation can be improved.

그러나, 상기 선행발명의 반응성 염료는 통상적인 면 반응성 염료의 분자구조보다 크기 때문에, 염색과정 말미에서 미고착 염료 제거 작업에 어려움이 많아 습윤견뢰도가 떨어지는 단점이 지적되고 있다.However, since the reactive dye of the prior invention is larger than the molecular structure of conventional cotton reactive dyes, it is pointed out that the disadvantages of wet fastness due to the difficulty in removing the unfixed dye at the end of the dyeing process.

따라서 이러한 종래 문제점을 해소하면서, 염료 혼합으로 인해 재현성 있는 염색이 어려운 문제를 해소하기 위하여, 단일 구조의 견뢰도가 높은 중간색상 염료 개발이 필요하다.Therefore, in order to solve such a conventional problem, in order to solve the problem that reproducible dyeing is difficult due to dye mixing, it is necessary to develop a medium color dye having high fastness of a single structure.

본 발명의 목적은 색재현성이 우수한 단일구조의 올리브색 반응성 염료를 제공하는 것이다. It is an object of the present invention to provide a mono structured olive reactive dye having excellent color reproducibility.

본 발명은 하기 화학식 1로 표시되는 올리브색 반응성 염료를 제공한다.The present invention provides an olive reactive dye represented by the following formula (1).

화학식 1Formula 1

Figure 112010080573390-pat00005
Figure 112010080573390-pat00005

(상기 식에서,(Wherein,

M은 수소, 리튬, 나트륨, 칼륨 중 어느 하나이고, M is any one of hydrogen, lithium, sodium, potassium,

R은 아미노, N-메틸아미노, N-에틸아미노, N-(2-히드록시에틸)아미노, N-(2-카르복시에틸)아미노, 히드록시, 메톡시, 에톡시 중 어느 하나이고, R is any one of amino, N-methylamino, N-ethylamino, N- (2-hydroxyethyl) amino, N- (2-carboxyethyl) amino, hydroxy, methoxy, ethoxy,

X는 수소, 카르복시산, 술폰산 중 어느 하나이고, n은 1 또는 2이고, X is any one of hydrogen, carboxylic acid, sulfonic acid, n is 1 or 2,

A는

Figure 112010080573390-pat00006
또는
Figure 112010080573390-pat00007
이고, A is
Figure 112010080573390-pat00006
or
Figure 112010080573390-pat00007
ego,

상기에서 R1, R2는 독립적으로 수소, 메틸, 에틸, 메톡시, 에톡시, 술폰산 중 어느 하나이고, In the above, R 1 , R 2 is independently any one of hydrogen, methyl, ethyl, methoxy, ethoxy, sulfonic acid,

Z는 -SO2CH2CH2Y이며, Y는 메톡시카르보닐, 에톡시카르보닐, 설페이토, 포스페이토, 클로로, 브로모, 요오드 중 어느 하나이고, n은 1 또는 2이다.)Z is -SO 2 CH 2 CH 2 Y, Y is methoxycarbonyl, ethoxycarbonyl, sulfato, phosphate, chloro, bromo, iodine and n is 1 or 2. )

더욱 바람직하게는, 본 발명은 M은 수소, R은 아미노이고, X는 카르복시산 또는 술폰산이고, A는

Figure 112010080573390-pat00008
이고, Z는 -SO2CH2CH2Y이며, 상기 Y는 설페이토인 화합물인 것을 특징으로 하는 올리브색 반응성 염료를 제공한다. More preferably, in the present invention, M is hydrogen, R is amino, X is carboxylic acid or sulfonic acid, and A is
Figure 112010080573390-pat00008
And Z is -SO 2 CH 2 CH 2 Y, wherein Y is a sulfato compound.

본 발명은 청색 색소 모체와 황색 색소 모체를 한 분자로 결합시켜 단일구조의 올리브색을 구현하는 반응성 염료를 제공함으로써, 각 3원색의 배합으로 얻어진 염료로 구현되는 올리브색보다 색상차가 적고, 색재현성이 우수하다. The present invention provides a reactive dye that realizes a single structure of olive color by combining a blue pigment mother and a yellow pigment mother in one molecule, and thus has less color difference than the olive color realized by the dyes obtained by combining the three primary colors, and has excellent color reproducibility. Do.

또한, 본 발명의 올리브색 반응성 염료는 청색 색소 모체와 황색 색소 모체 결합으로 분자구조가 커져 수반되는 종래 문제가 해소된다. 즉, 본 발명의 올리브색 반응성 염료는 수세성이 우수하여. 염색과정에서 미고착 염료 제거 작업이 용이하여 습윤견뢰도가 우수한 장점이 있다.In addition, the olive-colored reactive dye of the present invention solves the conventional problem that the molecular structure is increased by the blue pigment parent and the yellow pigment parent bond. That is, the olive-colored reactive dye of the present invention is excellent in water washability. It is easy to remove the unfixed dye in the dyeing process, so it has the advantage of excellent wet fastness.

도 1은 본 발명의 올리브색 반응성 아조 염료함량에 따른 염색물의 빌드업 평가사진이고,
도 2는 본 발명의 올리브색 반응성 아조 염료 및 종래 배합염료를 이용하여 염색한 염색물을 20시간 노광한 후 색상차를 비교한 사진이고,
도 3은 본 발명의 올리브색 반응성 아조 염료를 이용한 염색물의 습윤견뢰도 평가사진이다. 1 is an evaluation picture of the build-up of the dye according to the olive-color reactive azo dye content of the present invention,
Figure 2 is a photograph comparing the color difference after 20 hours exposure of the dyeing dye using the olive-color reactive azo dye and the conventional compounding dye of the present invention,
Figure 3 is a photograph of the evaluation of the wet fastness of the dye using the olive-color reactive azo dye of the present invention.

이하, 본 발명을 더욱 상세히 설명하고자 한다.Hereinafter, the present invention will be described in more detail.

본 발명은 하기 화학식 1로 표시되는 올리브색 반응성 염료를 제공한다. The present invention provides an olive reactive dye represented by the following formula (1).

화학식 1Formula 1

Figure 112010080573390-pat00009
Figure 112010080573390-pat00009

(상기 식에서(In the above formula

M은 수소, 리튬, 나트륨, 칼륨 중 어느 하나이고, M is any one of hydrogen, lithium, sodium, potassium,

R은 아미노, N-메틸아미노, N-에틸아미노, N-(2-히드록시에틸)아미노, N-(2-카르복시에틸)아미노, 히드록시, 메톡시, 에톡시 중 어느 하나이고, R is any one of amino, N-methylamino, N-ethylamino, N- (2-hydroxyethyl) amino, N- (2-carboxyethyl) amino, hydroxy, methoxy, ethoxy,

X는 수소, 카르복시산, 술폰산 중 어느 하나이고, n은 1 또는 2이고, X is any one of hydrogen, carboxylic acid, sulfonic acid, n is 1 or 2,

A는

Figure 112010080573390-pat00010
또는
Figure 112010080573390-pat00011
이고, A is
Figure 112010080573390-pat00010
or
Figure 112010080573390-pat00011
ego,

상기에서 R1, R2는 독립적으로 수소, 메틸, 에틸, 메톡시, 에톡시, 술폰산 중 어느 하나이고, In the above, R 1 , R 2 is independently any one of hydrogen, methyl, ethyl, methoxy, ethoxy, sulfonic acid,

Z는 -SO2CH2CH2Y이며, Y는 메톡시카르보닐, 에톡시카르보닐, 설페이토, 포스페이토, 클로로, 브로모, 요오드 중 어느 하나이고, n은 1 또는 2이다.)Z is -SO 2 CH 2 CH 2 Y, Y is methoxycarbonyl, ethoxycarbonyl, sulfato, phosphate, chloro, bromo, iodine and n is 1 or 2. )

이에 본 발명은 올리브색 반응성 염료의 바람직한 일례로서, 하기 실시예에서는 화학식 2 내지 5로 표시되는 화합물에 대하여 구체적으로 설명하나, 이에 한정되는 것은 아니다.
Thus, the present invention is a preferred example of the olive-color reactive dye, in the following examples will be described in detail with respect to the compound represented by the formula (2-5), but is not limited thereto.

이하, 본 발명을 실시예에 의하여 상세히 설명한다. Hereinafter, the present invention will be described in detail with reference to examples.

하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다.The following examples are merely illustrative of the present invention, but the scope of the present invention is not limited to the following examples.

<실시예 1> 올리브색 반응성 염료 제조Example 1 Olive Reactive Dye Preparation

통상적인 방법으로 하기 화학식 (A)로 표시되는 화합물을 합성하였다. 상기 화학식 (A) 48.9g을 물 500g에 넣고 pH 7.0조건하에서 용해시켰다. 4-(2-설페이토에틸술포닐)아닐린(4-(2-Sulfatoethylsulfony)laniline) 29g을 물 200g에 분산시킨 후, 탄산나트륨 15% 수용액을 이용하여 pH 7.0으로 용해시킨다. 이 용액에 얼음 70g와 35% 염산 25g을 첨가한 후 아질산나트륨 7 g을 물 30g에 용해시킨 용액을 서서히 가하여 디아조 반응을 수행하였다. 상기 디아조 반응이 종료되면, 여분의 아질산염을 설파민산으로 제거한 후, 화학식 (A) 용액에 서서히 첨가하였다. 상기 투입이 종료되면 15% 탄산나트륨 수용액을 이용하여 pH 6.5로 서서히 조절하면서 약 2시간 동안 교반하여 반응을 종결시켰다. 종결된 반응액을 분무 건조하여, 95g의 하기 화학식 2로 표시되는 목적화합물을 제조하였다. The compound represented by the following general formula (A) was synthesize | combined by the conventional method. 48.9 g of Formula (A) was added to 500 g of water, and dissolved under pH 7.0. 29 g of 4- (2-sulfatoethylsulfonyl) aniline (4- (2-Sulfatoethylsulfony) laniline) was dispersed in 200 g of water, and then dissolved in pH 7.0 using an aqueous 15% sodium carbonate solution. 70 g of ice and 25 g of 35% hydrochloric acid were added to the solution, and a solution in which 7 g of sodium nitrite was dissolved in 30 g of water was gradually added to carry out a diazo reaction. When the diazo reaction was completed, excess nitrite was removed with sulfamic acid, and then slowly added to the solution of formula (A). When the addition was completed, the reaction was terminated by stirring for about 2 hours while slowly adjusting to pH 6.5 using an aqueous 15% sodium carbonate solution. The terminated reaction solution was spray dried to prepare 95 g of the target compound represented by Chemical Formula 2.

Figure 112012064870507-pat00028
Figure 112012064870507-pat00028

<실시예 2> 올리브색 반응성 염료 제조Example 2 Preparation of Olive Reactive Dye

상기 실시예 1의 화학식 (A) 색소에, 2-메톡시-4-(2- 설페이토에틸술포닐)아닐린 32g를 사용하는 것을 제외하고는, 상기 실시예1과 동일한 방법으로 반응시켜, 화학식 3으로 표시되는 목적화합물 110g을 제조하였다. remind Except for using 32 g of 2-methoxy-4- (2-sulfatoethylsulfonyl) aniline in the dye of formula (A) of Example 1, the reaction was carried out in the same manner as in Example 1, 110g of the target compound represented by 3 was prepared.

Figure 112012064870507-pat00029
Figure 112012064870507-pat00029

<실시예 3> 올리브색 반응성 염료 제조Example 3 Preparation of Olive Reactive Dye

통상적인 방법으로 하기 화학식 (B)로 표시되는 화합물을 합성하였다. 상기 화학식 (B) 45.3g을 물 500g에 넣고 pH 7.0조건하에서 용해시켰다. 4-(2-설페이토에틸술포닐)아닐린 29g을 물 200g에 분산시킨 후, 탄산나트륨 15% 수용액을 이용하여 pH 7.0으로 용해시킨다. 이 용액에 얼음 70g와 35% 염산 25g을 첨가한 후 아질산나트륨 7 g을 물 30g에 용해시킨 용액을 서서히 가하여 디아조 반응을 수행하였다. 상기 디아조 반응이 종료되면, 여분의 아질산염을 설파민산으로 제거한 후, 화학식 (B) 용액에 서서히 첨가하였다. 상기 투입이 종료되면 15% 탄산나트륨 수용액을 이용하여 pH 6.5로 서서히 조절하면서 약 2시간 동안 교반하여 반응을 종결시켰다. 종결된 반응액을 분무 건조하여, 90g의 화학식 4로 표시되는 목적화합물을 제조하였다. The compound represented by the following general formula (B) was synthesize | combined by the conventional method. 45.3 g of Formula (B) was added to 500 g of water, and dissolved under pH 7.0. 29 g of 4- (2-sulfatoethylsulfonyl) aniline are dispersed in 200 g of water, and then dissolved in pH 7.0 using an aqueous 15% sodium carbonate solution. 70 g of ice and 25 g of 35% hydrochloric acid were added to the solution, and a solution in which 7 g of sodium nitrite was dissolved in 30 g of water was gradually added to carry out a diazo reaction. When the diazo reaction was completed, excess nitrite was removed with sulfamic acid, and then slowly added to the formula (B) solution. When the addition was completed, the reaction was terminated by stirring for about 2 hours while slowly adjusting to pH 6.5 using an aqueous 15% sodium carbonate solution. The terminated reaction solution was spray dried to prepare 90 g of the target compound represented by Chemical Formula 4.

Figure 112012064870507-pat00030
Figure 112012064870507-pat00030

<실시예 4> 올리브색 반응성 염료 제조Example 4 Olive Reactive Dye Preparation

상기 실시예 3의 화학식 (B) 색소에, 2-메톡시-4-(2-설페이토에틸술포닐)아닐린 32g을 사용하는 것을 제외하고는, 상기 실시예3과 동일한 방법으로 반응시켜, 화학식 5로 표시되는 목적화합물을 105g을 제조하였다. remind Except for using 32 g of 2-methoxy-4- (2-sulfatoethylsulfonyl) aniline in the dye of formula (B) of Example 3, the reaction was carried out in the same manner as in Example 3, 105 g of the target compound represented by 5 was prepared.

Figure 112012064870507-pat00031
Figure 112012064870507-pat00031

<실험예 1> 염색 직후의 염색 색상차 비교Experimental Example 1 Dyeing Color Difference Immediately After Dyeing

상기 실시예 1에서 제조된 올리브색 반응성 염료 분말 0.5g을 물 100g에 용해시키고 무수 망초 10g과 면 10g을 넣고 60℃에서 20분간 진탕한 후 탄산나트륨 4 g을 서서히 첨가하여 1시간 동안 진탕시켜 염색을 수행하였다. 상기 염색이 완료된 후 찬물로 충분히 수세한 후 비이온계 계면활성제로 95∼100℃에서 5분 동안 소오핑(soaping)한 후 찬물로 수세하여 제반 견뢰도가 우수한 올리브색상의 면 염색물을 제조하였다. 0.5 g of the olive-colored reactive dye powder prepared in Example 1 was dissolved in 100 g of water, 10 g of anhydrous forget-me-not and 10 g of cotton were shaken at 60 ° C. for 20 minutes, and 4 g of sodium carbonate was slowly added to shake for 1 hour to perform dyeing. It was. After the dyeing was completed, washed with cold water sufficiently and then soaped with a nonionic surfactant at 95 ~ 100 ℃ for 5 minutes (soaping) and washed with cold water to prepare an olive-colored cotton dyeing with excellent fastness.

반면에, 황색 반응성 염료(C. I. Reactive Yellow 145) 및 청색 반응성 염료(C. I. Reactive Blue 221)를 배합하여 올리브색 반응성 염료를 준비하고, 염색대상물인 면 중량 대비 상기 염색물 올리브색 반응성 염료를 각각 1.0중량%, 3.0 중량% 및 5.0중량%로 첨가하고 상기와 동일한 방법으로 수행하여, 올리브색상의 면 염색물을 제조하였다. 그 결과를 비교예 1 내지 3으로 분류하고, 그 결과를 도 1에 기재하였다. On the other hand, by combining a yellow reactive dye (CI Reactive Yellow 145) and a blue reactive dye (CI Reactive Blue 221) to prepare an olive-colored reactive dye, 1.0% by weight of each of the dyeing olive-colored reactive dye relative to the weight of the dyeing target, Olive dye cotton dyeing was prepared by adding 3.0 wt% and 5.0 wt% and performing the same method as described above. The results were classified into Comparative Examples 1 to 3, and the results are shown in FIG .

도 1은 본 발명의 올리브색 반응성 아조 염료함량에 따른 염색물의 빌드업 평가결과로서, 황색 반응성 염료(C. I. Reactive Yellow 145) 및 청색 반응성 염료(C. I. Reactive Blue 221)를 배합하여 제조된 올리브색 반응성 염료는 염색과정에서 상기 배합 염료의 함량증가에 따라, 면 염색물간의 빌드업(Build-up)이 상대적으로 낮았으며, 반면에, 본 실시예 1에서 제조된 단일 구조의 올리브색 반응성 염료를 사용한 경우, 그 염료함량 증가에 따라, 염색물의 염색농도가 증가하므로 빌드업이 우수하였다. 1 is a build-up evaluation result of the dye according to the olive-color reactive azo dye content of the present invention, the olive-reactive dye prepared by combining a yellow reactive dye (CI Reactive Yellow 145) and a blue reactive dye (CI Reactive Blue 221) is dyed According to the increase of the content of the blended dye in the process, the build-up between the cotton dyeings was relatively low, while in the case of using the olive-colored reactive dye having a single structure prepared in Example 1, the dye As the content increased, the dyeing concentration of the dyeing increased, so the buildup was excellent.

<실험예 2> 20시간 노광 후 견뢰도 측정Experimental Example 2 Fastness Measurement After 20-Hour Exposure

실시예 1에서 제조된 올리브색 반응성 염료 1.0중량% 및 비교예에서 제조된 배합염료를 동량 사용하여 얻은 각각의 염색물을 20시간 노광시킨 후, 측정한 물성 결과를 하기 표 1에 기재하였고, 그 외관을 도 2에 나타내었다. After each exposure of the dyeings obtained by using 1.0% by weight of the olive-colored reactive dye prepared in Example 1 and the same amount of the combined dye prepared in Comparative Example for 20 hours, the measured physical properties are shown in Table 1 below . Is shown in FIG. 2 .

Figure 112010080573390-pat00016
Figure 112010080573390-pat00016

상기 표 1로부터 본 발명의 단일구조의 올리브색 반응성 염료를 사용한 염색물의 경우, 우수한 일광견뢰도를 보여준다. 노광조건에 따른 색상차 결과, 본 발명의 올리브색 반응성 염료를 사용한 염색물의 경우, 현저히 낮은 수치로 확인하였다. In the case of the dyeing using the olive-colored reactive dye of the monostructure of the present invention from Table 1, it shows excellent light fastness. As a result of the color difference according to the exposure conditions, in the case of the dyeing using the olive-colored reactive dye of the present invention, it was confirmed with a significantly low value.

도 2는 본 발명의 올리브색 반응성 아조 염료 및 종래 배합염료를 이용하여 염색한 염색물을 20시간 노광한 후의 각각의 색상차를 비교한 사진이다. 그 결과, 본 발명의 염료를 이용한 경우, 상대적으로 염색초기의 올리브색에 가까운 색상을 유지하였다. Figure 2 is a photograph comparing the color difference after 20 hours exposure of the dye dye dyed using the olive-color reactive azo dye of the present invention and a conventional compound dye. As a result, in the case of using the dye of the present invention, a relatively close to the olive color of the initial dyeing was maintained.

<실험예 3> 습윤견뢰도 평가Experimental Example 3 Evaluation of Wet Fastness

실시예 1에서 제조된 올리브색 반응성 염료 5.0중량%로 염색된 염색천 2.5g과 염색되지 않은 흰 천 2.5g을 물 100㎖+탄산나트륨 0.2g+세제 0.5g을 잘 혼합하여 용해한 물에 포개어 넣고, 60℃에서 30분 동안 진탕한 후 수세하여 건조하였다. 같은 방법으로 비교예 3의 염색천 2.5g과 염색되지 않은 흰 천 2.5g을 물, 탄산나트륨, 세제 혼합 용액에 포개어 넣고 진탕 후 수세 건조하였다. 또한, 비교예 3의 배합염료로 염색된 염색천과 염색되지 않은 흰 천을 상기와 동일한 방식으로 수행하여, 각 흰 천에 대한 오염도를 비교하여 도 3에 나타내었다. 2.5 g of dyed cloth and 2.5 g of undyed white cloth, dyed with 5.0% by weight of the olive-colored reactive dye prepared in Example 1, were mixed well with 100 ml of water + 0.2 g of sodium carbonate + 0.5 g of detergent, and placed in dissolved water. After shaking for 30 minutes at, washed with water and dried. In the same manner, 2.5g of dyed cloth and 2.5g of undyed white cloth of Comparative Example 3 were overlaid in a mixture of water, sodium carbonate and detergent, shaken, and washed with water. Further, as compared white cloth is not dyed and the dyed cloth dyed with the dye formulation of Example 3 performed in the same manner, are shown in Figure 3 by comparing the pollution level of each white cloth.

도 3은 본 발명의 올리브색 반응성 아조 염료를 이용한 염색물의 습윤견뢰도 평가사진으로서, 실시예 1에서 제조된 올리브색 반응성 염료로 염색된 염색천(왼쪽)과 함께 진탕한 흰 천은 거의 오염되지 않았다(우측). 반면에 비교예3의 시료와 함께 진탕한 흰 천은 상당히 오염되었다(좌측). 상기 결과로부터, 본 발명의 올리브색 반응성 염료의 우수한 습윤견뢰도(세탁견뢰도)를 확인하였다.3 is a wet fastness evaluation photograph of the dye using the olive-color reactive azo dye of the present invention, the white cloth shaken with the dyed cloth (left) stained with the olive-colored reactive dye prepared in Example 1 was hardly contaminated (right) . On the other hand, the white cloth shaken with the sample of Comparative Example 3 was significantly contaminated (left). From the above results, the excellent wet fastness (washing fastness) of the olive-colored reactive dye of the present invention was confirmed.

상기에서 살펴본 바와 같이, 본 발명은 청색 색소 모체와 황색 색소 모체를 한 분자로 결합시켜 단일구조의 올리브색 반응성 염료를 제공하였다.As described above, the present invention provides a single structure of an olive-colored reactive dye by combining the blue pigment parent and the yellow pigment parent with one molecule.

본 발명의 올리브색 반응성 염료는 종래 3원색의 배합으로 얻어진 염료에 의해 구현되는 올리브색보다 색상차가 적고, 색재현성이 우수하다. The olive-colored reactive dye of the present invention has a smaller color difference and excellent color reproducibility than the olive color embodied by a dye obtained by a conventional combination of three primary colors.

또한, 본 발명의 올리브색 반응성 염료는 수세성이 우수하여. 염색과정에서 미고착 염료 제거 작업이 용이하여 습윤견뢰도가 우수하므로, 면반응성 염료로서 유용하다.
In addition, the olive-colored reactive dye of the present invention is excellent in water washability. It is useful as a cotton reactive dye because it is easy to remove unfixed dye during dyeing and has excellent wet fastness.

이상에서 본 발명은 기재된 구체예에 대해서만 상세히 설명되었지만 본 발명의 기술사상 범위 내에서 다양한 변형 및 수정이 가능함은 당업자에게 있어서 명백한 것이며, 이러한 변형 및 수정이 첨부된 특허청구범위에 속함은 당연한 것이다.While the invention has been shown and described with reference to certain exemplary embodiments thereof, it will be understood by those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the invention as defined by the appended claims.

Claims (5)

하기 화학식 1로 표시되는 올리브색 반응성 염료:
화학식 1
Figure 112012064870507-pat00017

상기 식에서
M은 수소, 리튬, 나트륨, 칼륨 중 어느 하나이고,
R은 아미노, N-메틸아미노, N-에틸아미노, N-(2-히드록시에틸)아미노, N-(2-카르복시에틸)아미노, 히드록시, 메톡시, 에톡시 중 어느 하나이고,
X는 수소, 카르복시산, 술폰산 중 어느 하나이고, n은 1 또는 2이고,
A는
Figure 112012064870507-pat00018
이고,
상기에서 R1은 독립적으로 수소, 메틸, 에틸, 메톡시, 에톡시, 술폰산 중 어느 하나이고,
Z는 -SO2CH2CH2Y이며, Y는 메톡시카르보닐, 에톡시카르보닐, 설페이토, 포스페이토, 클로로, 브로모, 요오드 중 어느 하나이고, n은 1 또는 2이다.An olive reactive dye represented by the following Chemical Formula 1:
Formula 1
Figure 112012064870507-pat00017

In the above formula
M is any one of hydrogen, lithium, sodium, potassium,
R is any one of amino, N-methylamino, N-ethylamino, N- (2-hydroxyethyl) amino, N- (2-carboxyethyl) amino, hydroxy, methoxy, ethoxy,
X is any one of hydrogen, carboxylic acid, sulfonic acid, n is 1 or 2,
A is
Figure 112012064870507-pat00018
ego,
R 1 in the above is independently any one of hydrogen, methyl, ethyl, methoxy, ethoxy, sulfonic acid,
Z is -SO 2 CH 2 CH 2 Y, Y is methoxycarbonyl, ethoxycarbonyl, sulfato, phosphate, chloro, bromo, iodine and n is 1 or 2. 제1항에 있어서, 하기 화학식 2로 표시되는 화합물인 것을 특징으로 하는 상기 올리브색 반응성 염료.
화학식 2
Figure 112012064870507-pat00032
The olive-colored reactive dye according to claim 1, which is a compound represented by the following Chemical Formula 2.
Formula 2
Figure 112012064870507-pat00032
 제1항에 있어서, 하기 화학식 3으로 표시되는 화합물인 것을 특징으로 하는 상기 올리브색 반응성 염료.
화학식 3
Figure 112012064870507-pat00033
The olive-colored reactive dye according to claim 1, which is a compound represented by the following Chemical Formula 3.
Formula 3
Figure 112012064870507-pat00033
 제1항에 있어서, 하기 화학식 4로 표시되는 화합물인 것을 특징으로 하는 상기 올리브색 반응성 염료.
화학식 4
Figure 112012064870507-pat00034
According to claim 1, wherein the olive reactive dye characterized in that the compound represented by the formula (4).
Formula 4
Figure 112012064870507-pat00034
 제1항에 있어서, 하기 화학식 5로 표시되는 화합물인 것을 특징으로 하는 상기 올리브색 반응성 염료.
화학식 5
Figure 112012064870507-pat00035
According to claim 1, wherein the olive reactive dye characterized in that the compound represented by the formula (5).
Formula 5
Figure 112012064870507-pat00035
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4746324A (en) 1985-12-18 1988-05-24 Hoechst Aktiengesellschaft Isothermal rapid-dyeing process for wool with vinyl sulfone type reactive dyes and sulfuric acid added at dyeing temperature
US5393884A (en) 1993-06-14 1995-02-28 Hoechst Celanese Corporation Fiber reactive anthraquinone dyes
US5409916A (en) 1993-06-14 1995-04-25 Hoechst Celanese Corporation Fiber reactive anthraquinone dyes
US5944855A (en) 1995-11-23 1999-08-31 Ciba Specialty Chemicals Corporation Process for dichromatic or trichromatic dyeing or printing

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4746324A (en) 1985-12-18 1988-05-24 Hoechst Aktiengesellschaft Isothermal rapid-dyeing process for wool with vinyl sulfone type reactive dyes and sulfuric acid added at dyeing temperature
US5393884A (en) 1993-06-14 1995-02-28 Hoechst Celanese Corporation Fiber reactive anthraquinone dyes
US5409916A (en) 1993-06-14 1995-04-25 Hoechst Celanese Corporation Fiber reactive anthraquinone dyes
US5944855A (en) 1995-11-23 1999-08-31 Ciba Specialty Chemicals Corporation Process for dichromatic or trichromatic dyeing or printing

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