KR100499448B1 - Reactive black dye composition - Google Patents
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
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Abstract
본 발명은 셀룰로오즈 섬유, 레이온 섬유 등의 날염 또는 연속염색시 알칼리 염욕내에서 우수한 안정성을 나타낼뿐만 아니라, 혼방염색시 나일론등 타 섬유에 대한 오염성이 적고, 세탁견뢰도, 일광견뢰도가 우수한 반응성 흑색 염료 조성물에 관한 것으로, 본 발명의 염료 조성물은 하기 일반식[Ⅰ]로 표시되는 염료 화합물과 하기의 일반식[Ⅱ]∼[Ⅵ]으로 표시되는 화합물중 어느하나를 함유하는 흑색염료 조성물에 다음 일반식(Ⅶ)로 표시되는 염료화합물을 첨가하여 조성되는 것을 특징으로한다.The present invention not only shows excellent stability in alkali dye baths in printing or continuous dyeing of cellulose fibers, rayon fibers, etc., but also has a low staining resistance to other fibers such as nylon during blending dyeing, and has good washing fastness and light fastness. The dye composition of the present invention relates to a black dye composition containing any one of a dye compound represented by the following general formula [I] and a compound represented by the following general formula [II] to [VI] The dye compound represented by (iii) is added to the composition.
상기 일반식[Ⅰ]∼일반식[Ⅶ]에서, X는 -SO2Cl와같이 치환반응에 의한 에스테르화가 가능한 기이고, M은 수소 또는 금속염을 나타낸다. A는 클로로 또는 플로르기이며, R1, R2, R3는 각각 독립적으로 수소, 메틸, 에틸, 메톡시, 또는 에톡시기이고, R4는 -CH2CH2OSO3H 또는 -CH2=CH2이다. n은 0∼2의 정수이며, R5는 수소, 메틸, 에틸, 메톡시, 에톡시, 카르복실기 또는 클로르기이고, Y는 수소 또는 설폰기이며, Y1은 수소, 설폰기, 카르복실기, -CH2CH2OSO3H, 또는 -CH2=CH2기이고, Y2은 수소, 메틸, 에틸, 메톡시, 에톡시, 설폰기, 또는 카르복실기이고, Z1은 수소, Z2은 수소, 메틸, 또는 에틸기이다.In the general formulas [I] to [VIII], X is a group capable of esterification by a substitution reaction such as -SO 2 Cl, and M represents hydrogen or a metal salt. A is a chloro or flor group, R 1 , R 2 , R 3 are each independently hydrogen, methyl, ethyl, methoxy, or ethoxy group, and R 4 is —CH 2 CH 2 OSO 3 H or —CH 2 = CH 2 . n is an integer of 0 to 2, R 5 is hydrogen, methyl, ethyl, methoxy, ethoxy, carboxyl group or chlor group, Y is hydrogen or sulfone group, Y 1 is hydrogen, sulfone group, carboxyl group, -CH 2 CH 2 OSO 3 H, or —CH 2 = CH 2 group, Y 2 is hydrogen, methyl, ethyl, methoxy, ethoxy, sulfone group, or carboxyl group, Z 1 is hydrogen, Z 2 is hydrogen, methyl Or ethyl group.
Description
본 발명은 셀룰로오즈 섬유, 레이온 섬유 또는 이들의 혼방섬유등을 짙은 흑색으로 염색하기 위한 반응성 염료 조성물에 관한 것이다. 보다 상세하게는 나일론등의 타 섬유에 대한 오염성이 적고, 기존 염료에 비해 세탁견뢰도, 일광견뢰도가 우수한 반응성 흑색 염료 조성물에 관한 것이다.The present invention relates to a reactive dye composition for dyeing cellulose fibers, rayon fibers or blended fibers thereof in dark black. More specifically, the present invention relates to a reactive black dye composition which is less contaminant to other fibers such as nylon and has excellent washing fastness and light fastness compared to conventional dyes.
구체적으로는 하기 일반식[Ⅰ]로 표시되는 유리산형태의 염료 60∼95 중량%와 하기 일반식[Ⅱ]∼[Ⅵ]으로 표시되는 유리산 형태의 염료 2∼15 중량%와 하기 일반식[Ⅶ]로 표시되는 유리산 형태의 염료 2∼30 중량%를 혼합한 반응성 염료 조성물에 관한 것이다.Specifically, 60 to 95 wt% of the free acid dye represented by the following general formula [I], and 2 to 15 wt% of the free acid form represented by the following general formula [II] to [VI] and the following general formula It relates to the reactive dye composition which mixed 2-30 weight% of the dye of the free acid form represented by [i].
본 발명의 염료 조성물은 날염 또는 연속염색시 알칼리 염욕내에서 우수한 안정성을 나타낼뿐만 아니라, 발염성이 양호하며, 용해도가 현저히 개선된 것이다.The dye composition of the present invention not only exhibits excellent stability in alkali salt baths in printing or continuous dyeing, but also has good printability and markedly improved solubility.
여기에서, X는 -SO2Cl과 같이 치환반응에 의한 에스테르화 가능한 기이고, M은 수소 또는 금속염을 나타낸다.Here, X is an esterifiable group by substitution reaction like -SO 2 Cl and M represents hydrogen or a metal salt.
여기에서, X는 치환반응에 의한 에스테르화 가능한 기이고, M은 수소 또는 금속염을 나타낸다. A는 클로로 또는 플로르기이며, R1, R2,는 각각 독립적으로 수소, 메틸, 에틸, 메톡시, 또는 에톡시기이다.Here, X is an esterifiable group by substitution reaction, and M represents hydrogen or a metal salt. A is a chloro or flor group, and R 1 , R 2 , are each independently hydrogen, methyl, ethyl, methoxy, or ethoxy group.
여기에서, X는 치환반응에 의한 에스테르화 가능한 기이고, M은 수소 또는 금속염을 나타낸다. A는 클로로 또는 플로르기이며, R1, R2, R3는 각각 독립적으로 수소, 메틸, 에틸, 메톡시, 또는 에톡시기이고, R4는 -CH2CH2OSO3 H 또는 -CH2=CH2이다.Here, X is an esterifiable group by substitution reaction, and M represents hydrogen or a metal salt. A is a chloro or flor group, R 1 , R 2 , R 3 are each independently hydrogen, methyl, ethyl, methoxy, or ethoxy group, and R 4 is —CH 2 CH 2 OSO 3 H or —CH 2 = CH 2 .
여기에서, X는 치환반응에 의한 에스테르화 가능한 기이고, M은 수소 또는 금속염을 나타낸다. R1, R2는 각각 독립적으로 수소, 메틸, 에틸, 메톡시, 또는 에톡시기이다.Here, X is an esterifiable group by substitution reaction, and M represents hydrogen or a metal salt. R 1 and R 2 are each independently hydrogen, methyl, ethyl, methoxy, or ethoxy group.
여기에서, X는 치환반응에 의한 에스테르화 가능한 기이고, M은 수소 또는 금속염을 나타낸다. R1, R2는 각각 독립적으로 수소, 메틸, 에틸, 메톡시, 또는 에톡시기이다.Here, X is an esterifiable group by substitution reaction, and M represents hydrogen or a metal salt. R 1 and R 2 are each independently hydrogen, methyl, ethyl, methoxy, or ethoxy group.
여기에서, X는 치환반응에 의한 에스테르화 가능한 기이고, M은 수소 또는 금속염을 나타낸다. R1, R2는 각각 독립적으로 수소, 메틸, 에틸, 메톡시, 또는 에톡시기이다. n은 0∼2의 정수이며, R5는 수소, 메틸, 에틸, 메톡시, 에톡시, 카르복실기 또는 클로르기이다.Here, X is an esterifiable group by substitution reaction, and M represents hydrogen or a metal salt. R 1 and R 2 are each independently hydrogen, methyl, ethyl, methoxy, or ethoxy group. n is an integer of 0-2, R <5> is hydrogen, methyl, ethyl, methoxy, ethoxy, a carboxyl group, or a chlor group.
여기에서, X는 치환반응에 의한 에스테르화 가능한 기이고, M은 수소 또는 금속염을 나타낸다. R1, R2는 각각 독립적으로 수소, 메틸, 에틸, 메톡시, 또는 에톡시기이다. Y는 수소 또는 설폰기이며, Y1은 수소, 설폰기, 카르복실기, -CH2CH2OSO3H, -CH2=CH2로 정의되며, Y2은 수소, 메틸, 에틸, 메톡시, 에톡시, 설폰기, 카르복실기이고, Z1은 수소, Z2은 수소, 메틸, 또는 에틸기이다.Here, X is an esterifiable group by substitution reaction, and M represents hydrogen or a metal salt. R 1 and R 2 are each independently hydrogen, methyl, ethyl, methoxy, or ethoxy group. Y is hydrogen or sulfone group, Y 1 is defined as hydrogen, sulfone group, carboxyl group, -CH 2 CH 2 OSO 3 H, -CH 2 = CH 2 , Y 2 is hydrogen, methyl, ethyl, methoxy, It is a oxy, sulfone group, and a carboxyl group, Z <1> is hydrogen, Z <2> is hydrogen, methyl, or an ethyl group.
종래의 셀룰로오즈 섬유, 레이온 섬유 또는 혼방섬유등을 짙은 흑색으로 염색하는데 사용되는 반응성 염료 조성물로는 하기 일반식[Ⅰ]로 표시되는 염료 60∼90 중량%와 하기 일반식[Ⅷ]로 표시되는 염료 5∼30 중량%와 하기 일반식[Ⅸ]로 표시되는 염료 5∼30 중량%로 조성된 것이있다.As a reactive dye composition used to dye conventional cellulose fibers, rayon fibers or blended fibers in a dark black color, 60 to 90% by weight of a dye represented by the following general formula [I] and a dye represented by the following general formula [VII] 5-30 weight% and 5-30 weight% of dyes represented by the following general formula [V].
상기식에서, X는 치환반응에 의한 에스테르화 가능한 기이고, M은 수소 또는 금속염을 나타낸다. R1, R2는 각각 독립적으로 수소, 메틸, 에틸, 메톡시, 또는 에톡시기이며, R은 염소 또는 -CH2CH2OSO3H, -CH2=CH2를 함유하는 방향족 아민이다.그 밖에도 상기 일반식(Ⅰ)로 표시되는 염료 화합물과 상기 일반식(Ⅱ)~(Ⅴ)으로 표시되는 염료화합물 중 어느하나를 함유하여 조성되는 흑색염료 조성물도 제안된바 있다.Wherein X is an esterifiable group by substitution reaction and M represents hydrogen or a metal salt. R 1 , R 2 are each independently hydrogen, methyl, ethyl, methoxy, or ethoxy group, and R is chlorine or an aromatic amine containing -CH 2 CH 2 OSO 3 H, -CH 2 = CH 2 . In addition, there has also been proposed a black dye composition comprising any one of the dye compounds represented by the general formula (I) and the dye compounds represented by the general formulas (II) to (V).
종래의 반응성 흑색 염료 조성물은 워시오프성, 세탁견뢰도 및 일반 제반견뢰도가 불량하여 셀룰로오즈 이외의 타섬유 즉, 나일론등에 오염성이 크고, 알칼리 날염욕이나 알칼리 연속염색욕에서 매우 약한 성질을 가지고 있기 때문에, 시간이 변화함에 따라 염료의 분해현상에 의한 용해도 저하 및 염착율의 감소현상으로 인하여 염색농도가 크게 떨어지고 짙은 흑색의 색상을 유지하기가 어려운 단점이 있었다.Since the conventional reactive black dye composition has poor wash-off, wash fastness and general fastness, it is highly contaminated to other fibers other than cellulose, such as nylon, and has very weak properties in alkaline printing bath or alkaline continuous dye bath. As the time was changed, the dye concentration was greatly decreased and it was difficult to maintain a dark black color due to a decrease in solubility and a decrease in dyeing rate due to dye decomposition.
본 발명의 목적은 셀룰로오즈섬유, 레이온섬유 및 이들의 혼방섬유를 흑색으로 염색시 타섬유에 대한 오염성이 적고, 세탁견뢰도 및 일광견뢰도가 우수한 반응성 흑색 염료 조성물을 제공하는데 있다.SUMMARY OF THE INVENTION An object of the present invention is to provide a reactive black dye composition which is less contaminated to other fibers when dyeing cellulose fibers, rayon fibers and blended fibers thereof in black, and has excellent washing fastness and light fastness.
본 발명자들은 종래 흑색염료조성물에 사용되고 있는 상기 일반식[Ⅰ]로 표시되는 화합물과 모노클로로 트리아진 또는 비닐 설폰기를 함유하며 옐로우 또는 오렌지 색상을 나타내는 상기 일반식[Ⅱ]∼[Ⅵ]으로 표시되는 염료화합물로 조성된 염료조성물에 상기 일반식[Ⅶ]로 표시되는 염료화합물을 첨가하여 염료조성물을 조성하여주므로서 염색후 색상의 심도가 높고 알카리욕 중에서 경시변화로 인하여 적흑색으로 변화되는 현상을 개선할수 있으며 타섬유에 대한 오염성이 적고 세탁견뢰도 및 일광견뢰도가 우수한 흑색 염료 조성물이 얻어지는 것을 확인하고 본 발명을 완성하게 되었다.The inventors of the present invention contain the compound represented by the general formula [I] and monochloro triazine or vinyl sulfone group, which are conventionally used in the black dye composition, and are represented by the general formulas [II] to [VI] which show yellow or orange color. By adding the dye compound represented by the general formula [Ⅶ] to the dye composition composed of the dye compound to form a dye composition, the color depth after dyeing is high and the phenomenon of changing to reddish black due to the change over time in the alkaline bath is improved. The present invention was completed by confirming that a black dye composition having low contamination with other fibers and excellent washing fastness and light fastness can be obtained.
본 발명은 하기 일반식[Ⅰ]로 표시되는 염료 화합물과 하기 일반식 [Ⅱ]∼[Ⅵ]로 표시되는 염료화합물 중 어느 하나를 함유하는 염료조성물에 하기 일반식[Ⅶ]로 표시되는 염료화합물을 첨가하여 조성되는 반응성 흑색 염료 조성물에 관한것이다.The present invention relates to a dye compound represented by the following general formula [VII] in a dye composition containing any one of the dye compounds represented by the following general formula [I] and the dye compounds represented by the following general formulas [II] to [VI] It relates to a reactive black dye composition formed by adding.
상기 일반식[Ⅰ]∼일반식[Ⅶ]에서, X는 치환반응에 의한 에스테르화 가능한 기이고, M은 수소 또는 금속염을 나타낸다. A는 클로로 또는 플로르기이며, R1, R2, R3는 각각 독립적으로 수소, 메틸, 에틸, 메톡시, 또는 에톡시기이고, R4는 -CH2CH2OSO3H 또는 -CH2=CH2이다. 또한, n은 0∼2의 정수이며, R5는 수소, 메틸, 에틸, 메톡시, 에톡시, 카르복실기 또는 클로르기이고, Y는 수소 또는 설폰기이며, Y1은 수소, 설폰기, 카르복실기, -CH2CH2OSO3H, -CH2=CH2로 정의되며, Y2은 수소, 메틸, 에틸, 메톡시, 에톡시, 설폰기, 또는 카르복실기이고, Z1은 수소, Z2은 수소, 메틸, 또는 에틸기이다.In the general formulas [I] to [VIII], X is an esterifiable group by a substitution reaction, and M represents hydrogen or a metal salt. A is a chloro or flor group, R 1 , R 2 , R 3 are each independently hydrogen, methyl, ethyl, methoxy, or ethoxy group, and R 4 is —CH 2 CH 2 OSO 3 H or —CH 2 = CH 2 . And n is an integer of 0 to 2, R 5 is hydrogen, methyl, ethyl, methoxy, ethoxy, carboxyl group or chlor group, Y is hydrogen or sulfone group, Y 1 is hydrogen, sulfone group, carboxyl group, And —CH 2 CH 2 OSO 3 H, —CH 2 = CH 2 , wherein Y 2 is hydrogen, methyl, ethyl, methoxy, ethoxy, sulfone group, or carboxyl group, Z 1 is hydrogen, Z 2 is hydrogen , Methyl, or ethyl group.
본 발명의 염료조성물은, 상기 일반식[Ⅰ]로 표시되는 유리산형태의 염료 60∼95 중량%와 상기 일반식[Ⅱ]∼[Ⅵ]으로 표시되는 유리산 형태의 염료 2∼15 중량%와 상기 일반식[Ⅶ]로 표시되는 유리산 형태의 염료 2∼30 중량%로 조성됨을 특징으로 한다.The dye composition of the present invention is 60 to 95% by weight of the dye in the form of the free acid represented by the general formula [I] and 2 to 15% by weight of the dye in the form of the free acid represented by the general formula [II] to [VI]. And 2 to 30% by weight of a dye in the form of a free acid represented by the general formula [VII].
상기와 같은 화합물로 구성된 염료 조성물은 셀룰로오즈 섬유, 레이온 섬유 또는 혼방섬유등의 염색시에 타섬유에 대한 오염성이 적고, 세탁견뢰도, 일광견뢰도등이 우수하며, 날염 또는 연속염색시 염료의 분해성이나 변색성이 적으며 경시변화에 안정하고 발염성이 우수한 장점을 가지고 있다.The dye composition composed of the above compounds is less contaminated to other fibers during dyeing of cellulose fibers, rayon fibers or blended fibers, has excellent washing fastness, light fastness, and the like, and decomposes or discolors dyes during printing or continuous dyeing. It has low strength, stable to change over time, and excellent flame retardancy.
이하 실시예를 통하여 본 발명을 구체적으로 설명한다. 그러나 하기 실시예만으로 본 발명이 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail through examples. However, the present invention is not limited only to the following examples.
<실시예 1><Example 1>
상기 일반식[Ⅰ]로 표시될수 있는 하기 구조식[10]의 화합물 100 중량부와 상기 일반식[Ⅲ]에 포함되는 하기 구조식[11]의 염료 화합물 11중량부 및 상기 일반식[Ⅶ]에 포함되는 하기 구조식 [37]의 염료 화합물 27중량부를 균일하게 혼합하여 하기 실험예에서 정한 방법에 따라 침염염색, 날염 및 연속염색을 수행한 후 염색농도와 제반견뢰도등을 시험하여 표 1에 나타내었다.100 parts by weight of the compound of the following structural formula [10] which can be represented by the general formula [I], 11 parts by weight of the dye compound of the following structural formula [11] included in the general formula [III] and the general formula 27 parts by weight of the dye compound of the following Structural Formula [37] were uniformly mixed, followed by dyeing, printing and continuous dyeing according to the method defined in the following Experimental Examples.
<실험예>Experimental Example
침염염색 시험예Dyeing dye test example
상기 실시예 1의 염료조성물의 0.4% 염료액 20㎖, 물 32㎖, 20% 황산나트륨 20㎖를 삼각플라스크에 넣고 여기에 면천 4g을 넣고 60℃에서 염색을 한다. 30분 후 20% 탄산나트륨 8㎖를 가하고 다시 60분간 염색을 하고 염색된 천을 끓는 물에서 10분간 세정한 후 수세, 건조시켜 2% 염색(o.w.f)을 시행한다. 8% 염색(o.w.f)을 할 경우에는 동일한 염료조성물 0.8% 염료액 40㎖, 물 12㎖, 20% 황산나트륨 20㎖를 삼각플라스크에 넣고 위와 동일한 염색과정을 실시하였다.20 ml of a 0.4% dye solution of the dye composition of Example 1, 32 ml of water, and 20 ml of 20% sodium sulfate were added to a Erlenmeyer flask, and 4 g of cotton cloth was added thereto and dyed at 60 ° C. After 30 minutes, 8 ml of 20% sodium carbonate is added and dyed again for 60 minutes. The dyed cloth is washed with boiling water for 10 minutes, washed with water and dried to perform 2% dyeing (o.w.f). In the case of 8% dyeing (o.w.f), 40 ml of 0.8% dye solution of the same dye composition, 12 ml of water, and 20 ml of 20% sodium sulfate were put into a Erlenmeyer flask and the same dyeing procedure was performed.
날염염색 시험예Printing dyeing test example
상기 실시예 1의 염료조성물 2g, 알긴산소다 30g, 탄산수소나트륨 1g, 요소 10g 및 물을 가해서 전량을 50g으로 한 후 혼합 교반한 후 면천에 프린팅한다. 그천을 건조기에서 건조하고 103 내지 105℃에서 15분간 쪄주어서 열고착시킨 후, 100℃에서 10분간 세정한 후 수세하였다.2 g of the dye composition of Example 1, 30 g of sodium alginate, 1 g of sodium bicarbonate, 10 g of urea and water were added to make the whole amount 50 g, followed by mixing and stirring, followed by printing on a cotton cloth. The cloth was dried in a drier, spun for 15 minutes at 103 to 105 DEG C, and heat-fixed, washed at 100 DEG C for 10 minutes, and washed with water.
연속염색 시험예Continuous dyeing test example
상기 실시예 1의 염료조성물 3g, 알긴산소다 0.4g 및 물 46.6g을 혼합하여 용해한후 이 용액에 알칼리제로서 수산화나트륨(32.3% 용액)을 적당히 가하여 연속염색을한다. 이때 패딩액의 온도는 30℃ 정도이며, 욕비는 70%이고, 패딩된 천을 60℃의 건조기에서 5분간 건조하고 103 내지 105℃에서 40초간 쪄주어서 열고착시킨 후, 100℃에서 10분간 세정한 후 수세하였다.3 g of the dye composition of Example 1, 0.4 g of sodium alginate, and 46.6 g of water are mixed and dissolved, followed by continuous dyeing with sodium hydroxide (32.3% solution) as an alkali agent. At this time, the temperature of the padding liquid is about 30 ℃, the bath ratio is 70%, the padded cloth was dried for 5 minutes in a dryer at 60 ℃, and then heat-fixed by heating for 40 seconds at 103 to 105 ℃, then washed for 10 minutes at 100 ℃ After washing with water.
하기 구조식의 염료화화합물들은 본 발명 실시예 2∼33에서 사용되는 화합물들을 나타낸 것이다. The dyeing compounds of the following structural formulas represent compounds used in Examples 2 to 33 of the present invention.
본 발명 실시예에서 이용되는 구조식[11]∼[60]의 화합물에서, 구조식[11]∼[16]의 화합물은 상기 일반식[Ⅲ]으로 표시되는 화합물이고 구조식[17]∼[24]의 화합물은 상기 일반식[Ⅱ]로 표시되는 화합물이고, 구조식[25]∼[28]의 화합물은 상기 일반식[Ⅳ]로 표시되는 화합물이고, 구조식[29]∼[33]의 화합물은 상기 일반식[Ⅴ]로 표시되는 화합물이고, 구조식[34]∼[36]의 화합물은 상기 일반식[Ⅵ]으로 표시되는 화합물이고 구조식[37]∼[60]의 화합물은 상기 일반식 [Ⅶ]로 표시되는 화합물이다.In the compounds of the formulas [11] to [60] used in the examples of the present invention, the compounds of the formulas [11] to [16] are the compounds represented by the general formula [III], and the compounds of the formulas [17] to [24] The compound is a compound represented by the general formula [II], the compounds of the formulas [25] to [28] are the compounds represented by the general formula [IV], and the compounds of the formulas [29] to [33] are the above general formulas. The compound represented by the formula [V], the compound represented by the formula [34] to [36] is the compound represented by the above general formula [VI], and the compound represented by the formula [37] to [60] is represented by the above general formula [VII] It is a compound to be displayed.
<실시예 2><Example 2>
구조식[10]의 화합물 100 중량부와 구조식[12]의 염료 화합물 11중량부 및 구조식[38]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [12] and 27 parts by weight of the dye compound of the formula [38] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 3><Example 3>
구조식[10]의 화합물 100 중량부와 구조식[13]의 염료 화합물 11중량부 및 구조식[39]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [13] and 27 parts by weight of the dye compound of the formula [39] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 4><Example 4>
구조식[10]의 화합물 100 중량부와 구조식[14]의 염료 화합물 11중량부 및 구조식[40]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [14] and 27 parts by weight of the dye compound of the formula [40] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 5>Example 5
구조식[10]의 화합물 100 중량부와 구조식[15]의 염료 화합물 11중량부 및 구조식[41]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [15] and 27 parts by weight of the dye compound of the formula [41] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 6><Example 6>
구조식[10]의 화합물 100 중량부와 구조식[16]의 염료 화합물 11중량부 및 구조식[42]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [16] and 27 parts by weight of the dye compound of the formula [42] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 7><Example 7>
구조식[10]의 화합물 100 중량부와 구조식[17]의 염료 화합물 11중량부 및 구조식[43]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [17] and 27 parts by weight of the dye compound of the formula [43] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 8><Example 8>
구조식[10]의 화합물 100 중량부와 구조식[18]의 염료 화합물 11중량부 및 구조식[44]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of formula [10], 11 parts by weight of the dye compound of formula [18] and 27 parts by weight of the dye compound of formula [44] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 9>Example 9
구조식[10]의 화합물 100 중량부와 구조식[19]의 염료 화합물 11중량부 및 구조식[45]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of formula [10], 11 parts by weight of the dye compound of formula [19] and 27 parts by weight of the dye compound of formula [45] were uniformly mixed, and the results were tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 10><Example 10>
구조식[10]의 화합물 100 중량부와 구조식[20]의 염료 화합물 11중량부 및 구조식[46]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [20] and 27 parts by weight of the dye compound of the formula [46] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 11><Example 11>
구조식 [10]의 화합물 100 중량부와 구조식 [21]의 염료 화합물 11중량부 및 구조식[47]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [21] and 27 parts by weight of the dye compound of the formula [47] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 12><Example 12>
구조식[10]의 화합물 100 중량부와 구조식[22]의 염료 화합물 11중량부 및 구조식[48]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [22] and 27 parts by weight of the dye compound of the formula [48] were uniformly mixed, and the experiments were carried out in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 13>Example 13
구조식[10]의 화합물 100 중량부와 구조식[23]의 염료 화합물 11중량부 및 구조식[49]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [23] and 27 parts by weight of the dye compound of the formula [49] were uniformly mixed, and the experiments were carried out in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 14><Example 14>
구조식[10]의 화합물 100 중량부와 구조식[24]의 염료 화합물 11중량부 및 구조식[50]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [24] and 27 parts by weight of the dye compound of the formula [50] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 15><Example 15>
구조식[10]의 화합물 100 중량부와 구조식[25]의 염료 화합물 11중량부 및 구조식[51]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [25] and 27 parts by weight of the dye compound of the formula [51] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 16><Example 16>
구조식[10]의 화합물 100 중량부와 구조식[26]의 염료 화합물 11중량부 및 구조식[52]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [26] and 27 parts by weight of the dye compound of the formula [52] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 17><Example 17>
구조식[10]의 화합물 100 중량부와 구조식[27]의 염료 화합물 11중량부 및 구조식[53]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [27] and 27 parts by weight of the dye compound of the formula [53] were uniformly mixed, and the experiments were carried out in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 18>Example 18
구조식[10]의 화합물 100 중량부와 구조식[28]의 염료 화합물 11중량부 및 구조식[54]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [28] and 27 parts by weight of the dye compound of the formula [54] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 19>Example 19
구조식[10]의 화합물 100 중량부와 구조식[29]의 염료 화합물 11중량부 및 구조식[55]의 염료 화합물 27중량부를 균일하게 혼합하여 실험한 결과를 표 1에 나타내었다.Table 1 shows the results of uniformly mixing 100 parts by weight of the compound of formula [10], 11 parts by weight of the dye compound of formula [29] and 27 parts by weight of the dye compound of formula [55].
<실시예 20>Example 20
구조식[10]의 화합물 100 중량부와 구조식[30]의 염료 화합물 11중량부 및 구조식[56]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [30] and 27 parts by weight of the dye compound of the formula [56] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 21>Example 21
구조식[10]의 화합물 100 중량부와 구조식[31]의 염료 화합물 11중량부 및 구조식[57]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [31] and 27 parts by weight of the dye compound of the formula [57] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 22><Example 22>
구조식[10]의 화합물 100 중량부와 구조식[32]의 염료 화합물 11중량부 및 구조식[58]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of formula [10], 11 parts by weight of the dye compound of formula [32] and 27 parts by weight of the dye compound of formula [58] were uniformly mixed, and the experiments were carried out in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 23><Example 23>
구조식[10]의 화합물 100 중량부와 구조식[33]의 염료 화합물 11중량부 및 구조식[59]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [33] and 27 parts by weight of the dye compound of the formula [59] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 24><Example 24>
구조식[10]의 화합물 100 중량부와 구조식[34]의 염료 화합물 11중량부 및 구조식[60]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of formula [10], 11 parts by weight of the dye compound of formula [34] and 27 parts by weight of the dye compound of formula [60] were uniformly mixed, and the results were tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 25><Example 25>
구조식[10]의 화합물 100 중량부와 구조식[35]의 염료 화합물 11중량부 및 구조식[49]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [35] and 27 parts by weight of the dye compound of the formula [49] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 26>Example 26
구조식[10]의 화합물 100 중량부와 구조식[36]의 염료 화합물 11중량부 및 구조식[38]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [36] and 27 parts by weight of the dye compound of the formula [38] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 27>Example 27
구조식[10]의 화합물 100 중량부와 구조식[11]의 염료 화합물 11중량부 및 구조식[39]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [11] and 27 parts by weight of the dye compound of the formula [39] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 28><Example 28>
구조식[10]의 화합물 100 중량부와 구조식[11]의 염료 화합물 11중량부 및 구조식[50]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [11] and 27 parts by weight of the dye compound of the formula [50] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 29><Example 29>
구조식[10]의 화합물 100 중량부와 구조식[11]의 염료 화합물 11중량부 및 구조식[51]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [11] and 27 parts by weight of the dye compound of the formula [51] were uniformly mixed, and the experiments were carried out in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 30><Example 30>
구조식[10]의 화합물 100 중량부와 구조식[17]의 염료 화합물 11중량부 및 구조식[38]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [17] and 27 parts by weight of the dye compound of the formula [38] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 31><Example 31>
구조식[10]의 화합물 100 중량부와 구조식[17]의 염료 화합물 11중량부 및 구조식[39]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [17] and 27 parts by weight of the dye compound of the formula [39] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 32><Example 32>
구조식[10]의 화합물 100 중량부와 구조식[17]의 염료 화합물 11중량부 및 구조식[50]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [17] and 27 parts by weight of the dye compound of the formula [50] were uniformly mixed and tested in the same manner as in Example 1, and the results are shown in Table 1. Indicated.
<실시예 33><Example 33>
구조식[10]의 화합물 100 중량부와 구조식[17]의 염료 화합물 11중량부 및 구조식[51]의 염료 화합물 27중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결과를 표 1에 나타내었다.<비교예 1>일반식[10]의 화합물 100 중량부와 구조식[61]의 염료 화합물 11 중량부 및 구조식[62]의 염료화합물 27 중량부를 균일하게 혼합하여 실시예 1과 같은 방법으로 실험하고 그 결화를 표 1에 나타내었다 ---[61] ------[62]각종 견뢰도는 하기 설명된 방법에 의해 측정하였다.(1) 세탁 견뢰도 : ISO 105-C03 규정에 의해 실험. 염색포와 백포를 비누액 5g/ℓ, 소다회 2g/ℓ에서 steal ball 10개를 넣고, 60℃에서 30분간 작동.(2) 땀 견뢰도 : ISO 105-E04 규정에 의해 실험. ㉠ 산성 : L-Histidine 0.5g/ℓ에 NaH2PO4와 NaCl을 혼합하여 pH 5.5로 맞추고, 리판 사이에 천을 넣어, 규정압으로 38℃의 건조기에서 4시간 동안 유지한 후, 60℃ 이하에서 건조. ㉡ 알칼리성 : L-Histidine 0.5g/ℓ에 Na2HPO4와 NaCl을 혼합하여 pH 8로 맞추고, 산땀과 동일하게 실험.(3) 마찰 견뢰도 : ISO 105-X12 규정에 의해 실험100% 습윤포(습마찰)를 900g 하중을 가한 배면포에서 10초간 10회 왕 복 마찰 후 판정.(4) 염소수 견뢰도 : ISO 105-E03 규정에 의해 실험.유효염소 20㎖/ℓ, pH 8.5에서 1시간(RT)동안 처리.(5) 물 견뢰도 : ISO 105-E01 규정에 의해 실험.(6) 일광 견뢰도 : ISO 105-B02(Xenon Arc) 규정에 의해 실험.상기 비교예들은 일반식[Ⅰ]의 염료화합물과 일반식[Ⅱ]~[Ⅵ]으로 표시되는 염료화합물로 조성된 염료조성물에 대한 실험예이다.비교예 1은 일반식[Ⅰ]은 일반식[Ⅰ]의 염료화합물과 일반식[Ⅳ]의 염료화합물 및 일반식[Ⅱ]의 염료화합물로 조성된 염료조성물에 대한 실험예이고 비교예 2는 일반식[Ⅰ]의 염료화합물과 일반식[Ⅷ]의 염료화합물 및 일반식[Ⅸ]로 표시되는 염료화합물로 조성된 염료조성물에 대한 시점예이다.100 parts by weight of the compound of the formula [10], 11 parts by weight of the dye compound of the formula [17] and 27 parts by weight of the dye compound of the formula [51] were uniformly mixed, and the experiments were carried out in the same manner as in Example 1, and the results are shown in Table 1. Comparative Example 1 The same method as in Example 1 was carried out by uniformly mixing 100 parts by weight of the compound of formula [10], 11 parts by weight of the dye compound of formula [61] and 27 parts by weight of the dye compound of formula [62]. And the condensation is shown in the --- [61] ------ [62] Various fastnesses were measured by the method described below. (1) Wash fastnesses: tested according to ISO 105-C03. Dye cloth and white cloth are put in 10g steal ball in soap solution 5g / ℓ and soda ash 2g / ℓ, and run for 30 minutes at 60 ℃. (2) Sweat fastness: Experiment by ISO 105-E04. ㉠ Acid: L-Histidine 0.5g / L mixed NaH 2 PO 4 and NaCl to pH 5.5, put the cloth between the lipan, and maintained in a dryer at 38 ℃ for 4 hours at a specified pressure, and below 60 ℃ dry. ㉡ Alkaline: L-Histidine 0.5g / L mixed Na 2 HPO 4 and NaCl to pH 8 and experimented in the same manner as acid sweat. (3) Friction fastness: 100% wet cloth tested according to ISO 105-X12 (4) Chlorine water fastness: Tested according to ISO 105-E03. 1 hour (at 20 ml / l of effective chlorine, pH 8.5). (5) Water fastness: tested according to ISO 105-E01 specification. (6) Daylight fastness: tested according to ISO 105-B02 (Xenon Arc) specification. The above comparative examples are dyes of general formula [I]. An experimental example of a dye composition composed of a compound and a dye compound represented by formulas [II] to [VI]. Comparative Example 1 is a general formula [Ⅰ], a dye compound of the general formula [I] and a general formula [IV]. ] Is an experimental example of a dye composition composed of a dye compound of formula [II] and a dye compound of formula [II], and Comparative Example 2 is a dye compound of formula [I] and a dye compound of formula [염료] A is the time for an example of the dye composition in the dye composition of the compound represented by the general formula [Ⅸ].
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<표 1>TABLE 1
상기 표1에 나타낸 결과로부터 알 수 있는 바와 같이, 기존의 옐로우, 오렌지 염료 형태로서 향상시키기 어려웠던 각종 견뢰도 수치를 염료 분자내에 모노클로로트리아진 또는 비닐선폰기를 함유한 옐로우염료화합물과 다아조체를 첨가하여 디스아조반응물을 함유시킨 오렌지염료화합물을 첨가함으로써 흑색 색상의 심도를 향상시켰다. 비교에들에 비해 염색농도를 15 내지 25% 향상시켰으며, 염색시에 발생되는 타섬유에 대한 오염성을 감소시켰다. 즉, 표 1에서 보는 바와 같이 세탁, 땀, 물견뢰도등의 오염성이 2 또는 3등급이었으나, 4 또는 5등급으로 향상되었다. 일광견뢰도 또한 3 내지 4등급이었으나 5등급으로 많이 향상 시켰음을 알 수 있었다.As can be seen from the results shown in Table 1 above, the various fastness values that were difficult to improve as conventional yellow and orange dye forms were added to the dye molecule by adding a yellow dye compound and a polyazo compound containing a monochlorotriazine or vinyl sunphone group. The depth of black color was improved by adding the orange dye compound containing the disazo reactant. Compared with the comparison, the dyeing concentration was improved by 15 to 25%, and the staining on other fibers generated during dyeing was reduced. That is, as shown in Table 1, the contamination, such as washing, sweat, water fastness, etc. were 2 or 3 grades, but improved to 4 or 5 grades. Daylight fastness was also 3 to 4 grades, but was found to improve a lot to 5 grades.
본 발명의 염료 조성물은 셀룰로오즈섬유, 레이온섬유 및 이들의 혼방섬유를 흑색으로 염색시 옐로우, 오렌지 색상을 첨가함으로써 흑색 색상의 심도를 높였을 뿐만아니라, 염색시에 발생되는 타섬유에 대한 오염성을 감소시키고, 세탁견뢰도, 일광견뢰도 등 각종 견뢰도등을 향상 시키는 효과가 있다.The dye composition of the present invention not only increases the depth of black color by adding yellow and orange colors when cellulose fibers, rayon fibers, and blended fibers thereof are dyed to black, but also reduces contamination to other fibers generated during dyeing. It is effective to improve various fastness such as washing fastness, daylight fastness.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20170139280A (en) | 2016-06-09 | 2017-12-19 | 주식회사 오영 | Reactive dye composition |
| KR20190113403A (en) | 2018-03-28 | 2019-10-08 | 주식회사 오영 | Reactive Black Dye Composition and Methods for Dyeing Fiber Using the Same |
| KR20230053974A (en) | 2021-10-15 | 2023-04-24 | 충남대학교산학협력단 | Reactive disperse dye composition for dyeing using supercritical fluid and dyeing method using same |
| KR20230157040A (en) | 2022-05-09 | 2023-11-16 | 충남대학교산학협력단 | Reactive disperse dye composition and supercritical fluid dyeing method using same |
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| US5559215A (en) * | 1994-05-02 | 1996-09-24 | Hoechst Aktiengesellschaft | Black mixture of fibre-reactive azo dyes containing essentially a navy-blue disazo dye and an orange monoazo dye, as well as novel fibre-reactive phenylazonaphthol dyes containing A 2-(2'-sufophenylamino)-4-fluoro-1,3,5-triazin-6-ylamino group |
| US5611821A (en) * | 1995-09-16 | 1997-03-18 | Everlight Usa, Inc. | Black reactive dye composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20170139280A (en) | 2016-06-09 | 2017-12-19 | 주식회사 오영 | Reactive dye composition |
| KR20190113403A (en) | 2018-03-28 | 2019-10-08 | 주식회사 오영 | Reactive Black Dye Composition and Methods for Dyeing Fiber Using the Same |
| KR20230053974A (en) | 2021-10-15 | 2023-04-24 | 충남대학교산학협력단 | Reactive disperse dye composition for dyeing using supercritical fluid and dyeing method using same |
| KR20230157040A (en) | 2022-05-09 | 2023-11-16 | 충남대학교산학협력단 | Reactive disperse dye composition and supercritical fluid dyeing method using same |
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