KR20020021799A - Reactive black dye composition - Google Patents
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- KR20020021799A KR20020021799A KR1020020003235A KR20020003235A KR20020021799A KR 20020021799 A KR20020021799 A KR 20020021799A KR 1020020003235 A KR1020020003235 A KR 1020020003235A KR 20020003235 A KR20020003235 A KR 20020003235A KR 20020021799 A KR20020021799 A KR 20020021799A
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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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0047—Mixtures of two or more reactive azo dyes
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Abstract
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 -CH2CH2OSO3H 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 또는금속염을 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.Wherein X is an esterifiable group by substitution reaction and M represents hydrogen or a metal salt. R 1 and R 2 are each independently a hydrogen, methyl, ethyl, methoxy, or ethoxy group, and R is an aromatic amine containing chlorine or -CH 2 CH 2 OSO 3 H, -CH 2 = CH 2 .
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 화합물에 모노클로로 트리아진 또는 비닐 설폰기를 함유하며 옐로우 또는 오렌지 색상을 나타내는 상기 일반식[Ⅱ]∼[Ⅶ]로 표시되는 염료화합물을 일정범위로 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 monochloro triazine or vinyl sulfone groups in the compounds represented by the general formula [I], which are conventionally used for black dye compositions, and are represented by the general formulas [II] to [VII], which show yellow or orange color. By adding dye compound in a certain range to form dye composition, the color depth after dyeing can be improved, and the phenomenon of reddish black color due to change with time in alkaline bath can be improved. It was confirmed that an excellent black dye composition was obtained, and the present invention was completed.
본 발명은 하기 일반식[Ⅰ]로 표시되는 염료 화합물과 하기 일반식 [Ⅱ]∼[Ⅵ]로 표시되는 염료화합물을 적어도 1종 이상과 하기 일반식[Ⅶ]로 표시되는 염료화합물을 적어도 1종 이상 포함하는 반응성 흑색 염료 조성물에 관한것이다.The present invention provides at least one dye compound represented by the following general formula [I], at least one dye compound represented by the following general formulas [II] to [VI], and at least one dye compound represented by the following general formula [VII]: It relates to a reactive black dye composition comprising at least a species.
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.
또한, 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.Further, 60 to 95% by weight of the dye in the free acid form represented by the general formula [I], 2 to 15% by weight of the dye in the free acid form represented by the general formula [II] to [VI] and the general formula [ It is characterized in that it is composed of 2 to 30% by weight of the dye in the form of the free acid represented by iii.
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 하기 구조식[11]의 염료 화합물 11중량부 및 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.The following experiment was carried out by uniformly mixing 100 parts by weight of the compound of the following structural formula [10], 11 parts by weight of the dye compound of the following structural formula [11] and 27 parts by weight of the dye compound of the following structural formula [37] After dyeing, printing and continuous dyeing in accordance with the method set forth in the examples, the dyeing concentration and the overall fastness were tested and shown in Table 1.
<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.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. Indicated.
<비교예>Comparative Example
일반식[10]의 화합물 100 중량부와 일반식[61]의 염료 화합물 11중량부 및 일반식[62]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 [61] and 27 parts by weight of the dye compound of the formula [62] were uniformly mixed and tested in the same manner as in Example 1. Table 1 shows.
<표 1>TABLE 1
상기 표1의 비교예와 실험예의 결과로부터 알 수 있는 바와 같이, 염료 분자내에 모노클로로트리아진 또는 비닐설폰기를 함유한 옐로우, 오렌지 색상을 나타내는 염료화합물을 첨가함으로써 색상의 심도를 높였을 뿐만아니라, 염색시에 견뢰도 실험한 결과 타섬유에 대한 오염성이 적고, 세탁견뢰도, 일광견뢰도등이 향상되었음을 알 수 있었다.As can be seen from the results of Comparative Example and Experimental Example of Table 1, not only the depth of color was increased by adding a dye compound representing a yellow or orange color containing monochlorotriazine or vinyl sulfone group in the dye molecule. As a result of the fastness test at the time of dyeing, it was found that the contamination to other fibers was less, and the wash fastness and the light fastness were improved.
본 발명의 염료 조성물은 셀룰로오즈섬유, 레이온섬유 및 이들의 혼방섬유를 흑색으로 염색시 알칼리욕 중에서 적흑색으로 경시변화하는 현상을 개선시키고 타 섬유에 대한 오염성이 적으며 세탁견뢰도 및 일광견뢰도가 향상되는 효과가 있다. 경시변화로 인하여 적흑색으로 변화되는 현상을 개선할 수 있는 신규 반응성 흑색 염료 조성물을 제공하였다.The dye composition of the present invention improves the phenomena of changing cellulose fiber, rayon fiber, and blended fiber thereof to reddish black color in alkaline bath with time, and is less pollutant to other fibers, washing fastness and light fastness There is. It provides a novel reactive black dye composition that can improve the phenomenon of changing to red black due to the change over time.
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| KR20230053974A (en) | 2021-10-15 | 2023-04-24 | 충남대학교산학협력단 | Reactive disperse dye composition for dyeing using supercritical fluid and dyeing method using same |
| KR102647762B1 (en) | 2022-05-09 | 2024-03-13 | 충남대학교산학협력단 | Reactive disperse dye composition and supercritical fluid dyeing method using same |
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| US5611821A (en) * | 1995-09-16 | 1997-03-18 | Everlight Usa, Inc. | Black reactive dye composition |
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