TW202325695A - Dye for material with amide functional groups and dyeing method of using the same - Google Patents

Dye for material with amide functional groups and dyeing method of using the same Download PDF

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TW202325695A
TW202325695A TW110149267A TW110149267A TW202325695A TW 202325695 A TW202325695 A TW 202325695A TW 110149267 A TW110149267 A TW 110149267A TW 110149267 A TW110149267 A TW 110149267A TW 202325695 A TW202325695 A TW 202325695A
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dye
dyeing
dihydroxyindole
item
dyeing method
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TW110149267A
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TWI806322B (en
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黃偕倫
張珮菁
張昌榮
林忠德
林雅琳
廖弘玉
朱向元
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財團法人工業技術研究院
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Abstract

A dye for a material with amide functional groups and a dyeing method of using the same are provided. The dye includes a compound represented by Formula (I) and a solvent. Based on the total weight of the dye of 100 wt%, a content of the compound represented by Formula (I) is 40 wt% to 95 wt%. In Chemical Formula (I), R1, R2 and R3 are each independently H, -OH or -COOH, wherein at least one of R1, R2 and R3 is -OH or -COOH.

Description

用於具有醯胺官能基的材料的染料以及使用其的染色方法Dyes for materials having amide functional groups and dyeing methods using the same

本揭露是關於一種染料以及使用其的染色方法,且特別是關於一種用於醯胺官能基的材料的染料以及使用其的染色方法。The present disclosure relates to a dye and a dyeing method using the same, and in particular to a dye for an amide functional material and a dyeing method using the same.

含聚醯胺材料(例如尼龍材料)多是以酸性染料進行染色。酸性染料與含聚醯胺材料以離子鍵、氫鍵、凡得瓦爾力形成牢固的結合以進行染色。然而,目前常見的酸性染料大多為含有磺酸基(-SO 3H)的偶氮系染料(-N=N-),而生產此偶氮系染料的原料(例如苯胺(aniline)或其衍生物)具有致癌與毒害疑慮,未來將會遭受到禁用。 Polyamide-containing materials (such as nylon materials) are mostly dyed with acid dyes. Acid dyes and polyamide-containing materials form a strong combination of ionic bonds, hydrogen bonds, and van der Waals forces for dyeing. However, currently common acid dyes are mostly azo dyes (-N=N-) containing sulfonic acid groups (-SO 3 H), and the raw materials for producing such azo dyes (such as aniline or its derivatives substances) are suspected of being carcinogenic and toxic, and will be banned in the future.

因此,尋找一種不以苯胺作為原料、可用於含聚醯胺材料之染色,同時可降低對環境與對人類健康存在危害風險的染料,是目前研究人員急欲解決的問題。Therefore, finding a dye that does not use aniline as a raw material, can be used for dyeing polyamide-containing materials, and can reduce the risk of harm to the environment and human health is a problem that researchers are eager to solve.

本揭露提供一種染料,其不以苯胺作為原料、且對於具有醯胺官能基的材料具有優異的染色力度,不僅有利於低碳製程,更具有商業價值。The disclosure provides a dye that does not use aniline as a raw material and has excellent dyeing strength for materials with amide functional groups, which is not only beneficial to low-carbon manufacturing processes, but also has commercial value.

本揭露提供一種染色方法,其可應用於具有醯胺官能基的材料,並且可使染色的材料具有優異的染色力度。The disclosure provides a dyeing method, which can be applied to materials with amide functional groups, and can make the dyed materials have excellent dyeing strength.

本揭露提出一種染料,用於對具有醯胺官能基的材料進行染色,所述染料包括: 式(I)表示的化合物;以及 溶劑, (I) 在式(I)中,R 1、R 2及R 3各自獨立地為H、-OH或-COOH, 其中R 1、R 2及R 3中的至少一者為-OH或-COOH,且 按所述染料的總重量為100 wt%計,所述式(I)表示的化合物的含量為40 wt%至95 wt%。 The present disclosure proposes a dye for dyeing materials with amide functional groups, the dye comprising: a compound represented by formula (I); and a solvent, (I) In formula (I), R 1 , R 2 and R 3 are each independently H, -OH or -COOH, wherein at least one of R 1 , R 2 and R 3 is -OH or -COOH , and based on the total weight of the dye being 100 wt%, the content of the compound represented by the formula (I) is 40 wt% to 95 wt%.

本揭露提出一種染色方法,其包括使用染液與具有醯胺官能基的材料接觸,以進行染色步驟,其中染液包括包含式(I)表示的化合物的染料, (I) 在式(I)中,R 1、R 2及R 3各自獨立地為H、-OH或-COOH, 其中R 1、R 2及R 3中的至少一者為-OH或-COOH,且 按所述染料的總重量為100 wt%計,所述式(I)表示的化合物的含量為40 wt%至95 wt%。 The disclosure proposes a dyeing method, which includes using a dye solution to contact a material with an amide functional group to perform a dyeing step, wherein the dye solution includes a dye comprising a compound represented by formula (I), (I) In formula (I), R 1 , R 2 and R 3 are each independently H, -OH or -COOH, wherein at least one of R 1 , R 2 and R 3 is -OH or -COOH , and based on the total weight of the dye being 100 wt%, the content of the compound represented by the formula (I) is 40 wt% to 95 wt%.

基於上述,本揭露所提供的染料可用於聚醯胺材料的染色,且不以具有毒害疑慮的苯胺作為原料,有利於低碳製程之外,更可有效降低對環境與對人類健康危害的風險。Based on the above, the dyes provided in this disclosure can be used for dyeing polyamide materials, and do not use aniline, which is suspected of being toxic, as a raw material, which is not only beneficial to low-carbon manufacturing processes, but also can effectively reduce the risk of harm to the environment and human health. .

在本文中,由「一數值至另一數值」表示的範圍,是一種避免在說明書中一一列舉該範圍中的所有數值的概要性表示方式。因此,某一特定數值範圍的記載,涵蓋該數值範圍內的任意數值以及由該數值範圍內的任意數值界定出的較小數值範圍,如同在說明書中明文寫出該任意數值和該較小數值範圍一樣。Herein, a range indicated by "one value to another value" is a general representation which avoids enumerating all values in the range in the specification. Therefore, the description of a specific numerical range covers any numerical value in the numerical range and the smaller numerical range bounded by any numerical value in the numerical range, as if the arbitrary numerical value and the smaller numerical value are expressly written in the specification. same range.

本文使用的「約」、「近似」、「本質上」、或「實質上」包括所述值和在本領域普通技術人員確定的特定值的可接受的偏差範圍內的平均值,考慮到所討論的測量和與測量相關的誤差的特定數量(即,測量系統的限制)。例如,「約」可以表示在所述值的一個或多個標準偏差內,或例如±30%、±20%、±15%、±10%、±5%內。再者,本文使用的「約」、「近似」、「本質上」、或「實質上」可依量測性質或其它性質,來選擇較可接受的偏差範圍或標準偏差,而可不用一個標準偏差適用全部性質。As used herein, "about," "approximately," "essentially," or "essentially" includes the stated value and averages within acceptable deviations from the particular value as determined by one of ordinary skill in the art, taking into account the The measurement in question and the specific amount of error associated with the measurement (ie, the limitations of the measurement system). For example, "about" can mean within one or more standard deviations of the stated value, or for example within ±30%, ±20%, ±15%, ±10%, ±5%. Furthermore, the terms "about", "approximately", "essentially" or "substantially" used herein can choose a more acceptable range of deviation or standard deviation according to the nature of measurement or other properties, instead of using a standard Deviations apply to all properties.

為了提供一種不以苯胺作為原料、且可用於聚醯胺材料以及有利於低碳製程的染料,本揭露提出一種包含吲哚結構的染料以及使用其的染色方法,其可達到上述優點。以下,特舉實施方式作為本揭露確實能夠據以實施的範例。In order to provide a dye that does not use aniline as a raw material, can be used for polyamide materials, and is beneficial to low-carbon manufacturing processes, the present disclosure proposes a dye containing an indole structure and a dyeing method using the same, which can achieve the above advantages. Hereinafter, the implementation manners are specifically cited as an example in which the present disclosure can be actually implemented.

在本實施例中,本揭露的染料為用於對具有醯胺官能基的材料進行染色的染料。在一實施例中,具有醯胺官能基的材料例如是尼龍或具有醯胺官能基的人工皮革或前述之組合。在一實施例中,具有醯胺官能基的人工皮革例如是包括醯胺官能基的聚氨酯(Polyurethane, PU)。In this embodiment, the dyes of the present disclosure are dyes for dyeing amide-functional materials. In one embodiment, the material with amide functional groups is, for example, nylon or artificial leather with amide functional groups, or a combination thereof. In one embodiment, the artificial leather with amide functional groups is, for example, polyurethane (Polyurethane, PU) including amide functional groups.

在本實施例中,包含吲哚結構的染料包括以下式(I)表示的化合物以及溶劑, (I) 在式(I)中,R 1、R 2及R 3各自獨立地為H、-OH或-COOH, 其中R 1、R 2及R 3中的至少一者為-OH或-COOH。 In this embodiment, the dye containing an indole structure includes a compound represented by the following formula (I) and a solvent, (I) In formula (I), R 1 , R 2 and R 3 are each independently H, -OH or -COOH, wherein at least one of R 1 , R 2 and R 3 is -OH or -COOH .

在一實施例中,R 1與R 2中的至少一者為-OH,且R 3為H或-COOH。 In one embodiment, at least one of R 1 and R 2 is —OH, and R 3 is H or —COOH.

在一實施例中,所述式(I)表示的化合物可包括5,6-二羥基吲哚(5,6-dihydroxyindole;DHI)、5,6-二羥基吲哚-2-羧酸(5,6-dihydroxyindole-2-carboxylic acid;DHICA)或前述之組合。In one embodiment, the compound represented by the formula (I) may include 5,6-dihydroxyindole (5,6-dihydroxyindole; DHI), 5,6-dihydroxyindole-2-carboxylic acid (5 ,6-dihydroxyindole-2-carboxylic acid; DHICA) or a combination of the foregoing.

上述5,6-二羥基吲哚(DHI)與5,6-二羥基吲哚-2-羧酸(DHICA)的結構式分別如下所示。 (DHI)                   (DHICA) The structural formulas of the above-mentioned 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA) are shown below, respectively. (DHI) (DHICA)

在本實施例中,式(I)表示的化合物可由化學合成或生物合成所得。在一實施例中,生物合成例如是微生物的醱酵產物。需特別說明的是,本揭露的式(I)表示的化合物的生成不需使用苯胺或苯胺衍生物作為合成原料,因此可降低對環境與對人類健康危害的風險。In this embodiment, the compound represented by formula (I) can be obtained by chemical synthesis or biological synthesis. In one embodiment, biosynthesis is, for example, a fermentation product of microorganisms. It should be noted that the compound represented by formula (I) of the present disclosure does not need to use aniline or aniline derivatives as synthetic raw materials, thus reducing the risk of harm to the environment and human health.

在一實施例中,按染料的總重量為100 wt%計,式(I)表示的化合物的含量可為約40 wt%至95 wt%,例如可為約55 wt%至90wt%、60 wt%至85wt%、52 wt%、58wt%、66 wt%、73 wt%、76 wt%、87 wt%、92 wt%等,但本揭露不限於此。In one embodiment, based on the total weight of the dye as 100 wt%, the content of the compound represented by formula (I) can be about 40 wt% to 95 wt%, such as about 55 wt% to 90 wt%, 60 wt% % to 85 wt%, 52 wt%, 58 wt%, 66 wt%, 73 wt%, 76 wt%, 87 wt%, 92 wt%, etc., but the disclosure is not limited thereto.

在一實施例中,本揭露的染料包括一種式(I)表示的化合物,但本揭露不限於此。在另一實施例中,本揭露的染料包括不只一種,例如是兩種或多種式(I)表示的化合物。In one embodiment, the dye of the present disclosure includes a compound represented by formula (I), but the present disclosure is not limited thereto. In another embodiment, the dye of the present disclosure includes more than one, such as two or more compounds represented by formula (I).

在一實施例中,式(I)表示的化合物包括5,6-二羥基吲哚(DHI)以及5,6-二羥基吲哚-2-羧酸(DHICA),且5,6-二羥基吲哚與5,6-二羥基吲哚-2-羧酸的重量比可為約1:15至15:1,例如可為約1:12至12:1、1:10至10:1、1:8至8:1、1:5至5:1、1:3至3:1、1:2至2:1、1:9、5:5、7:3、9:1等,但本揭露不限於此。在一實施例中,使用者可依其所需求之色相(例如偏棕色或偏黑色)而選擇不同重量比之DHI與DHICA配製作為染料,並將所述染料應用具有醯胺官能基之材料的染色上。在一實施例中,具有醯胺官能基之材料例如是尼龍、人工皮革或前述之組合,但本揭露不限於此。In one embodiment, the compound represented by formula (I) includes 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA), and 5,6-dihydroxyindole The weight ratio of indole to 5,6-dihydroxyindole-2-carboxylic acid can be about 1:15 to 15:1, for example can be about 1:12 to 12:1, 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, 1:3 to 3:1, 1:2 to 2:1, 1:9, 5:5, 7:3, 9:1, etc., but The present disclosure is not limited thereto. In one embodiment, users can choose different weight ratios of DHI and DHICA to prepare dyes according to their desired hue (such as brownish or blackish), and use materials with amide functional groups for the dyestuffs. on the dyeing. In one embodiment, the material having the amide functional group is nylon, artificial leather or a combination thereof, but the disclosure is not limited thereto.

在本實施例中,染料的溶劑可包括水,例如是蒸餾水、去離子水、超純水、或前述之組合,但本揭露不限於此。在不致對環境與人類具危害風險的前提下,使用者可依實際需求選擇適合的溶劑進行染料的配製。In this embodiment, the dye solvent may include water, such as distilled water, deionized water, ultrapure water, or a combination thereof, but the disclosure is not limited thereto. Under the premise that there is no risk of harm to the environment and human beings, users can choose suitable solvents for the preparation of dyes according to actual needs.

在一實施例中,由本揭露的染料所染出的色相為黑色、棕色或兩者的混合色。在一實施例中,本揭露的染料包括5,6-二羥基吲哚(DHI),而由此染料所染出的色相為黑色。在另一實施例中,本揭露的染料包括5,6-二羥基吲哚-2-羧酸(DHICA),而由此染料所染出的色相為棕色。在一實施例中,本揭露的染料包括5,6-二羥基吲哚(DHI)以及5,6-二羥基吲哚-2-羧酸(DHICA),而由此染料所染出的色相為黑色、棕色或兩者的混合色。具體而言,可藉由調整5,6-二羥基吲哚(DHI)與5,6-二羥基吲哚-2-羧酸(DHICA)的比例來控制色相。更詳細言之,5,6-二羥基吲哚-2-羧酸(DHICA)的含量越高,色相越偏向棕色,而5,6-二羥基吲哚(DHI)的含量越高,色相越偏向黑色。In one embodiment, the hue dyed by the dye of the present disclosure is black, brown or a mixture thereof. In one embodiment, the dye of the present disclosure includes 5,6-dihydroxyindole (DHI), and the hue dyed by the dye is black. In another embodiment, the dye of the present disclosure includes 5,6-dihydroxyindole-2-carboxylic acid (DHICA), and the hue dyed by this dye is brown. In one embodiment, the dye disclosed herein includes 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA), and the hue dyed by the dye is Black, brown or a mixture of both. Specifically, the hue can be controlled by adjusting the ratio of 5,6-dihydroxyindole (DHI) to 5,6-dihydroxyindole-2-carboxylic acid (DHICA). In more detail, the higher the content of 5,6-dihydroxyindole-2-carboxylic acid (DHICA), the more brown the hue, and the higher the content of 5,6-dihydroxyindole (DHI), the more brown the hue. leaning toward black.

在一實施例中,所述染料是在酸性環境下進行染色。在一實施例中,本揭露的染料的pH值可為3.5至6.5,例如可為3.8至6.3、4.0至6.0、4.2至5.8、4.5至5.5等,但本揭露不限於此。在一實施例中,本揭露的染料的pH值可為4至6。染料在上述的pH值範圍,可確保被染色的材料具有優異的染色力度、水洗堅牢度、耐水洗牢度以及乾、溼摩擦牢度。在一實施例中,本揭露的染料可更包括酸鹼調整劑,本揭露的染料的pH值可以透過酸鹼調整劑來調節。在一實施例中,酸鹼調整劑例如是有機酸、有機鹼、無機酸、無機鹼、或前述之組合。In one embodiment, the dye is dyed in an acidic environment. In one embodiment, the pH value of the dye of the present disclosure may be 3.5 to 6.5, such as 3.8 to 6.3, 4.0 to 6.0, 4.2 to 5.8, 4.5 to 5.5, etc., but the present disclosure is not limited thereto. In one embodiment, the dye of the present disclosure may have a pH of 4-6. When the dye is in the above pH range, it can ensure that the dyed material has excellent dyeing strength, washing fastness, washing fastness and dry and wet rubbing fastness. In one embodiment, the dye of the present disclosure may further include a pH adjusting agent, and the pH of the dye of the present disclosure may be adjusted through the pH adjusting agent. In one embodiment, the acid-base regulator is, for example, an organic acid, an organic base, an inorganic acid, an inorganic base, or a combination thereof.

此外,本揭露亦提出一種使用上述染料的染色方法。在本實施例中,使用染液與具有醯胺官能基的材料接觸,以進行染色步驟。在本實施例中,染液包括上述的包含式(I)表示的化合物的染料,但本揭露不限於此。在本實施例中,具有醯胺官能基的材料在酸性環境下,-NH 2會形成-NH 3 +而帶有正電,本揭露的染料上的官能基(如羥基或羧基)則帶有負電,其會與具有醯胺官能基的材料以離子鍵結合,進而對材料進行染色。在一實施例中,染液可更包括至少一種其他染料,例如商用染料。 In addition, the present disclosure also proposes a dyeing method using the above-mentioned dyes. In this embodiment, a dyeing solution is used to contact the material with amide functional groups to perform the dyeing step. In this embodiment, the dye solution includes the above-mentioned dye containing the compound represented by formula (I), but the present disclosure is not limited thereto. In this embodiment, the material with amide functional group will form -NH 3 + in an acidic environment with positive charge, and the functional group (such as hydroxyl or carboxyl) on the dye of the present disclosure will have Negatively charged, it will ionic bond with the material with amide functional group, and then dye the material. In one embodiment, the dye solution may further include at least one other dye, such as a commercial dye.

在本實施例中,本揭露的染液中染料的濃度可為1%對織物重(on weight of the fabric,o.w.f.)至25%對織物重,例如可為2%至20%對織物重、5%至18%對織物重、8%至15%對織物重、10%對織物重、12.5%對織物重等,但本揭露不限於此。本揭露的染料在上述的濃度範圍內,可確保被染色的材料具有優異的染色力度、水洗堅牢度、耐水洗牢度以及乾、溼摩擦牢度。In this embodiment, the concentration of the dyestuff in the dye solution of the present disclosure may be 1% to 25% on weight of the fabric (on weight of the fabric, o.w.f.), such as 2% to 20% to the weight of the fabric, 5% to 18% by weight of fabric, 8% to 15% by weight of fabric, 10% by weight of fabric, 12.5% by weight of fabric, etc., but the disclosure is not limited thereto. The dyestuff disclosed in the present disclosure can ensure that the dyed material has excellent dyeing strength, washing fastness, washing fastness and dry and wet rubbing fastness within the above concentration range.

一般而言,在染整過程中,染色色深度(K/S, Color strength value)>3為染整可應用之基礎條件,而色深度之深淺與染料的使用量及其上色效率相關。當所使用的染液中染料的濃度低於1% o.w.f.時,由於染料的有色成分過低,將造成染色結果過淺(即K/S值小於3),染色效果不佳。相反地,如使用過量的染料(即大於25%對織物重),則染色後的排放殘液中含有過多染料,可能衍生提高廢水處理的成本與環境污染風險。Generally speaking, in the dyeing and finishing process, the dyeing color depth (K/S, Color strength value) > 3 is the basic condition for dyeing and finishing, and the depth of color strength is related to the amount of dye used and its coloring efficiency. When the concentration of the dye in the dyeing solution used is lower than 1% o.w.f., because the colored component of the dye is too low, the dyeing result will be too light (that is, the K/S value is less than 3), and the dyeing effect will be poor. Conversely, if an excessive amount of dye is used (that is, greater than 25% by weight of the fabric), the discharge residue after dyeing will contain too much dye, which may increase the cost of wastewater treatment and the risk of environmental pollution.

在本實施例中,染色步驟的反應溫度可為80℃至130℃,例如可為85℃至125℃、90℃至120℃、95℃至115℃、82℃、87℃、93℃、98℃、105℃、112℃、122℃等,但本揭露不限於此。在本實施例中,染色步驟的反應時間可為30分鐘至60分鐘,例如可為35分鐘至55分鐘、40分鐘至50分鐘、32分鐘、38分鐘、40分鐘、45分鐘、50分鐘、58分鐘等,但並不限於此。在本實施例中,染色步驟的反應pH值可為3.5至6.5,例如可為3.8至6.3、4.0至6.0、4.2至5.8、4.5至5.5等,但並不限於此。本揭露的染料在上述的反應條件進行染色,可確保被染色的材料具有優異的染色力度、水洗堅牢度、耐水洗牢度以及乾、溼摩擦牢度。In this embodiment, the reaction temperature of the dyeing step can be 80°C to 130°C, for example, it can be 85°C to 125°C, 90°C to 120°C, 95°C to 115°C, 82°C, 87°C, 93°C, 98°C °C, 105 °C, 112 °C, 122 °C, etc., but the present disclosure is not limited thereto. In this embodiment, the reaction time of the dyeing step can be 30 minutes to 60 minutes, such as 35 minutes to 55 minutes, 40 minutes to 50 minutes, 32 minutes, 38 minutes, 40 minutes, 45 minutes, 50 minutes, 58 minutes Minutes, etc., but not limited to this. In this embodiment, the reaction pH value of the dyeing step may be 3.5 to 6.5, such as 3.8 to 6.3, 4.0 to 6.0, 4.2 to 5.8, 4.5 to 5.5, etc., but not limited thereto. Dyeing the dyestuff disclosed in the present disclosure under the above reaction conditions can ensure that the dyed material has excellent dyeing strength, washing fastness, washing fastness and dry and wet rubbing fastness.

在本實施例中,在進行染色步驟以使具有醯胺官能基的材料染色之後,經染色的具有醯胺官能基的材料可進一步進行清洗處理,以移除多餘的染料。清洗處理可以使用水或洗劑等。In this embodiment, after the dyeing step is performed to dye the material with amide functional group, the dyed material with amide functional group can be further cleaned to remove excess dye. For the cleaning treatment, water, a lotion, or the like can be used.

此外,在本實施例中,不論是否進行清洗處理,經染色的具有醯胺官能基的材料會進行乾燥處理,以利後續應用。乾燥處理例如是自然風乾、熱風乾燥、旋轉乾燥、抽吸乾燥等。In addition, in this embodiment, no matter whether the washing process is performed or not, the dyed material with amide functional group will be dried for subsequent application. The drying treatment is, for example, natural air drying, hot air drying, spin drying, suction drying, and the like.

在本實施例中,經染色後的所述具有醯胺官能基的材料的乾、濕摩擦牢度測試(AATCC 8)為4至5級。經染色後的所述具有醯胺官能基的材料的耐水牢度測試(AATCC 107)為4至5級。經染色後的所述具有醯胺官能基的材料的水洗堅牢度測試(AATCC 61)為4至5級。經染色後的所述具有醯胺官能基的材料的L*值為8至60,a*值為-5至15,b*值為-10至25,K/S值為3至35。「L*」代表感知的亮度(Lightness),L* = 0指示黑色,而L* = 100指示白色。「a*」和「b*」代表人類視覺的四種獨特顏色:紅色、綠色、藍色和黃色,其中「a*」為紅/綠值(Red/Green Value),「a*」為負值指示綠色,而「a*」為正值指示紅色。「b*」為藍/黃值(Blue/Yellow Value),「b*」為負值指示藍色,而「b*」為正值指示黃色。In this embodiment, the dry and wet rubbing fastness test (AATCC 8) of the dyed material having amide functional groups is grade 4 to 5. The water fastness test (AATCC 107) of the dyed material with amide functional group is grade 4 to 5. The washing fastness test (AATCC 61) of the dyed material having an amide functional group is grade 4 to 5. The dyed material with amide functional groups has an L* value of 8 to 60, an a* value of -5 to 15, a b* value of -10 to 25, and a K/S value of 3 to 35. "L*" represents the perceived brightness (Lightness), L* = 0 indicates black, and L* = 100 indicates white. "a*" and "b*" represent the four unique colors of human vision: red, green, blue and yellow, where "a*" is the Red/Green Value and "a*" is negative A value indicates green, while a positive value of "a*" indicates red. "b*" is blue/yellow value (Blue/Yellow Value), negative value of "b*" indicates blue, and positive value of "b*" indicates yellow.

此外,如上所述,經染色後的所述具有醯胺官能基的材料的色相為黑色、棕色或兩者的混合色。此外,藉由調整染料中不同式(I)表示的化合物的比例,可依需求來控制色相。In addition, as mentioned above, the hue of the dyed material having amide functional groups is black, brown or a mixture of the two. In addition, by adjusting the ratio of the compounds represented by different formulas (I) in the dye, the hue can be controlled as required.

藉由進行以上步驟,即可完成本揭露的一實施方式所提出的染色方法。值得說明的是,本揭露的染料使用非苯胺或非苯胺衍生物作為合成原料,不僅可降低環境傷害以及人類健康的風險,且符合尼龍產業的永續及低碳製程的要求。此外,本揭露的染料可有效地對具有醯胺官能基的材料進行染色,並可有不同色澤的染色配方,有利於應用於尼龍機能型市場。By performing the above steps, the dyeing method proposed in an embodiment of the present disclosure can be completed. It is worth noting that the dyes disclosed herein use non-aniline or non-aniline derivatives as synthetic raw materials, which can not only reduce environmental damage and human health risks, but also meet the requirements of sustainable and low-carbon manufacturing processes in the nylon industry. In addition, the dye disclosed in the present disclosure can effectively dye materials with amide functional groups, and can have dyeing formulas of different shades, which is beneficial for the nylon functional market.

下文將參照實施例更具體地描述本揭露。雖然描述了以下實施例,但是在不逾越本揭露範疇的情況下,可適當地改變所用材料、其量及比率、處理細節以及處理流程等等。因此,不應根據下文所述的實驗對本揭露作出限制性地解釋。Hereinafter, the present disclosure will be described more specifically with reference to Examples. Although the following examples are described, materials used, their amounts and ratios, processing details, processing flow, and the like can be appropriately changed without departing from the scope of the present disclosure. Accordingly, the present disclosure should not be construed restrictively based on the experiments described below.

實驗例Experimental example 1:1: 使用包含Use contains DHICADHICA 的染料對尼龍布進行染色dyes for dyeing nylon cloth

< 實施例Example 1>1>

首先,配製包含有90wt%之5,6-二羥基吲哚-2-羧酸(DHICA)作為染料,接著將染料加入水中,以配製成2% o.w.f.的染液,並將其pH值調整為5。接著,使尼龍布浸於所述染液中,並在反應溫度為105℃、pH值為5的條件下進行染色50分鐘後,於65℃下進行皂洗15分鐘,之後以清水清洗並進行乾燥,以得到實施例1的經染色的尼龍布。First, prepare a dye containing 90wt% 5,6-dihydroxyindole-2-carboxylic acid (DHICA), then add the dye to water to prepare a 2% o.w.f. dye solution, and adjust its pH for 5. Next, soak the nylon cloth in the dye solution, and dye it at a reaction temperature of 105°C and a pH value of 5 for 50 minutes, then soap it at 65°C for 15 minutes, then wash it with water and carry out Dried to obtain the dyed nylon cloth of Example 1.

< 實施例Example 2>2>

使用與實施例1類似的方法進行染色,其差別只在於實施例2的染料濃度為5% o.w.f.。Dyeing was carried out in a manner similar to that of Example 1, the only difference being that the dye concentration of Example 2 was 5% o.w.f.

< 實施例Example 3>3>

使用與實施例1類似的方法進行染色,其差別只在於實施例3的染料濃度為10% o.w.f.。Dyeing was carried out in a manner similar to Example 1 except that the dye concentration of Example 3 was 10% o.w.f.

< 實施例Example 4>4>

使用與實施例1類似的方法進行染色,其差別只在於實施例4的染料濃度為15% o.w.f.。Dyeing was carried out in a manner similar to that of Example 1 except that the dye concentration of Example 4 was 15% o.w.f.

< 實施例Example 5>5>

使用與實施例1類似的方法進行染色,其差別只在於實施例5的染料濃度為20% o.w.f.。Dyeing was carried out in a manner similar to Example 1 except that the dye concentration of Example 5 was 20% o.w.f.

< 實施例Example 6>6>

使用與實施例1類似的方法進行染色,其差別只在於實施例6的染料濃度為25% o.w.f.。Dyeing was carried out in a manner similar to Example 1 except that the dye concentration of Example 6 was 25% o.w.f.

在獲得實施例1-6的經染色的尼龍布後,對實施例1-6的經染色的尼龍布分別進行染色力度的量測以及物性測試,其結果如下表1所示。 〈染色力度的量測〉 After obtaining the dyed nylon cloth of Examples 1-6, the measurement of the dyeing strength and the physical property test were respectively carried out on the dyed nylon cloth of Examples 1-6, and the results are shown in Table 1 below. <Measurement of dyeing strength>

使用色彩分光光度計(i1Basic Pro 2)分別對實施例1-6的經染色的尼龍布的染色力度進行量測,其單位為K/S。吸收光的物質主要是染料,當染料濃度越高時,吸收強度越大,散射強度則越小。而染色力度就是由Kubelka-Munk理論(Kubelka-Munk theory)所提出的以下公式來計算: , 其中K為吸收係數,S為散射係數,R為最大吸收波長之反射率。 The dyeing strengths of the dyed nylon cloths of Examples 1-6 were measured with a color spectrophotometer (i1Basic Pro 2), and the unit is K/S. The light-absorbing substance is mainly a dye, and the higher the dye concentration, the greater the absorption intensity and the smaller the scattering intensity. The dyeing strength is calculated by the following formula proposed by Kubelka-Munk theory (Kubelka-Munk theory): , where K is the absorption coefficient, S is the scattering coefficient, and R is the reflectance of the maximum absorption wavelength.

經染色的尼龍布的物性測試所採用的評價方法為水洗堅牢度測試(AATCC 61)、耐水牢度測試(AATCC 107)、以及乾、溼摩擦牢度測試(AATCC 8)。The evaluation methods used in the physical property test of dyed nylon cloth are washing fastness test (AATCC 61), water fastness test (AATCC 107), and dry and wet rubbing fastness test (AATCC 8).

水洗堅牢度測試(AATCC 61)以及耐水牢度測試(AATCC 107)為經水洗後變褪色程度的評價,其分為五級,級數越高代表越不會退色。The washing fastness test (AATCC 61) and the water fastness test (AATCC 107) are used to evaluate the degree of fading after washing. It is divided into five grades, and the higher the grade, the less it will fade.

乾、溼摩擦牢度測試(AATCC 8)為經乾式摩擦或溼式摩擦後變褪色程度的評價,其分為五級,級數越高代表越不會退色。The dry and wet rubbing fastness test (AATCC 8) is an evaluation of the degree of fading after dry rubbing or wet rubbing. It is divided into five grades, and the higher the grade, the less fading.

值得注意的是,水洗堅牢度測試(AATCC 61)、耐水牢度測試(AATCC 107)、以及乾、溼摩擦牢度測試在四級以上才具有商業化價值。It is worth noting that the washing fastness test (AATCC 61), water fastness test (AATCC 107), and dry and wet rubbing fastness test have commercial value above level 4.

[表1]   % o.w.f. L* a* b* K/S 經染色後的尼龍布的顏色 水洗堅牢度測試 (AATCC 61) 耐水牢度測試   (AATCC 107) 乾、溼摩擦牢度測試   (AATCC 8) 實施例1 2 52.6 5.5 14.1 4.0 棕色 4-5 4-5 4-5 實施例2 5 49.2 6.9 14.8 4.7 棕色 4-5 4-5 4-5 實施例3 10 45.1 6.9 15.8 7.1 棕色 4-5 4-5 4-5 實施例4 15 38.9 6.0 13.5 9.2 棕色 4-5 4-5 4-5 實施例5 20 41.2 8.3 16.9 9.6 棕色 4-5 4-5 4-5 實施例6 25 34.2 6.9 13.8 13.8 棕色 4 4 4 [Table 1] % owf L* a* b* K/S The color of dyed nylon cloth Washing Fastness Test (AATCC 61) Water Fastness Test (AATCC 107) Dry and wet rubbing fastness test (AATCC 8) Example 1 2 52.6 5.5 14.1 4.0 brown 4-5 4-5 4-5 Example 2 5 49.2 6.9 14.8 4.7 brown 4-5 4-5 4-5 Example 3 10 45.1 6.9 15.8 7.1 brown 4-5 4-5 4-5 Example 4 15 38.9 6.0 13.5 9.2 brown 4-5 4-5 4-5 Example 5 20 41.2 8.3 16.9 9.6 brown 4-5 4-5 4-5 Example 6 25 34.2 6.9 13.8 13.8 brown 4 4 4

由上述的評價結果來看,使用本揭露的染料(DHICA)進行染色後的實施例1-5的尼龍布的水洗堅牢度測試、耐水牢度測試、以及乾、溼摩擦牢度測試皆為4-5級,而實施例6的尼龍布的水洗堅牢度測試、耐水牢度測試、以及乾、溼摩擦牢度測試為4級,顯示以本揭露的染料所染色獲得的尼龍布具有良好的水洗堅牢度、耐水牢度、乾、溼摩擦牢度等綜合性能,符合產業可利用性。此外,隨著染料的濃度(% o.w.f.)越高,其色深度(即K/S值)越高。再者,在本揭露的染色條件下,實施例1-6的尼龍布的顏色具有棕色色相。From the above evaluation results, the washing fastness test, water fastness test, and dry and wet rubbing fastness test of the nylon cloth of Examples 1-5 dyed using the disclosed dye (DHICA) are all 4 -5 grade, while the washing fastness test, water fastness test and dry and wet rubbing fastness test of the nylon cloth of embodiment 6 are grade 4, showing that the nylon cloth obtained by dyeing with the dyestuff disclosed has good water washing Comprehensive properties such as fastness, water fastness, dry and wet rubbing fastness, etc., are in line with industrial applicability. In addition, as the dye concentration (% o.w.f.) is higher, its color depth (ie K/S value) is higher. Furthermore, under the dyeing conditions disclosed in the present disclosure, the color of the nylon fabrics of Examples 1-6 has a brown hue.

實驗例Experimental example 2:2: 使用包含Use contains DHIDHI 的染料對尼龍布進行染色dyes for dyeing nylon cloth

< 實施例Example 7>7>

首先,配製包含有90wt%之5,6-二羥基吲哚(DHI)作為染料,接著將染料加入水中,以配製成5% o.w.f.的染液,並將其pH值調整為5。接著,使尼龍布浸於所述染液中,並在反應溫度為105℃、pH值為5的條件下進行染色50分鐘後,於65℃進行皂洗15分鐘,之後以清水清洗並進行乾燥,以得到實施例7的經染色的尼龍布。Firstly, 90wt% of 5,6-dihydroxyindole (DHI) was prepared as a dye, and then the dye was added to water to prepare a 5% o.w.f. dye solution, and its pH value was adjusted to 5. Next, immerse the nylon cloth in the dye solution, and dye it at a reaction temperature of 105°C and a pH value of 5 for 50 minutes, then soap it at 65°C for 15 minutes, then wash it with water and dry it. , to obtain the dyed nylon cloth of embodiment 7.

在獲得實施例7的經染色的尼龍布後,對實施例7的經染色的尼龍布進行染色力度的量測以及物性測試,其結果如下表2所示。After obtaining the dyed nylon cloth of Example 7, the measurement of dyeing strength and the physical property test were carried out on the dyed nylon cloth of Example 7, and the results are shown in Table 2 below.

[表2]   % o.w.f. L* a* b* K/S 經染色後的尼龍布的顏色 水洗堅牢度測試 (AATCC 61) 耐水牢度測試   (AATCC 107) 乾、溼摩擦牢度測試   (AATCC 8) 實施例7 5 12.3 3.7 1.4 21.3 黑色 4-5 4-5 4-5 [Table 2] % owf L* a* b* K/S The color of dyed nylon cloth Washing Fastness Test (AATCC 61) Water Fastness Test (AATCC 107) Dry and Wet Rubbing Fastness Test (AATCC 8) Example 7 5 12.3 3.7 1.4 21.3 black 4-5 4-5 4-5

由上述的評價結果來看,使用本揭露的染料(DHI)進行染色後的實施例7的尼龍布的水洗堅牢度測試、耐水牢度測試、以及乾、溼摩擦牢度測試皆為4-5級,顯示以本揭露的染料所染色獲得的尼龍布具有良好的水洗堅牢度、耐水牢度、乾、溼摩擦牢度等綜合性能,符合產業可利用性。此外,在本揭露的染色條件下,實施例7的尼龍布的顏色具有黑色色相。From the above evaluation results, the washing fastness test, water fastness test, and dry and wet rubbing fastness test of the nylon cloth of Example 7 dyed with the disclosed dye (DHI) are all 4-5 Grade, showing that the nylon cloth obtained by dyeing with the dye disclosed in this disclosure has good comprehensive properties such as washing fastness, water fastness, dry and wet rubbing fastness, and is in line with industrial applicability. In addition, under the dyeing conditions of the present disclosure, the color of the nylon cloth of Example 7 has a black hue.

實驗例Experimental example 3:3: 使用包含Use contains DHICADHICA 的染料對人工皮革進行染色dyes for artificial leather

< 實施例Example 8>8>

首先,配製包含有90wt%之5,6-二羥基吲哚-2-羧酸(DHICA)作為染料,接著將染料加入水中,以配製成2% o.w.f.的染液,並將其pH值調整為5。接著,使人工皮革(具有醯胺官能基的聚氨酯)浸於所述染液中,並在反應溫度為90℃、pH值為5的條件下進行染色50分鐘後,於65℃進行皂洗15分鐘,之後以清水清洗並進行乾燥,以得到實施例8的經染色的人工皮革。First, prepare a dye containing 90wt% 5,6-dihydroxyindole-2-carboxylic acid (DHICA), then add the dye to water to prepare a 2% o.w.f. dye solution, and adjust its pH for 5. Next, the artificial leather (polyurethane with amide functional groups) is immersed in the dyeing solution, and after dyeing at a reaction temperature of 90°C and a pH value of 5 for 50 minutes, soaping is carried out at 65°C for 15 minutes. Minutes, then washed with clear water and dried to obtain the dyed artificial leather of Example 8.

< 實施例Example 9>9>

使用與實施例8類似的方法進行染色,其差別只在於實施例9與實施例8的人工皮革的聚氨酯組成。詳細來說,實施例9與實施例8的人工皮革是各自由不同製程所合成,其中實施例8是由聚酯纖維與聚氨酯所組成的人工皮革,而實施例9是由聚酯超細纖維與聚氨酯所組成的人工皮革。Dyeing was carried out in a similar manner to that of Example 8, the only difference being the polyurethane composition of the artificial leathers of Example 9 and Example 8. In detail, the artificial leather of Example 9 and Example 8 are synthesized by different processes, wherein Example 8 is an artificial leather composed of polyester fiber and polyurethane, while Example 9 is made of polyester microfiber Artificial leather composed of polyurethane.

在獲得實施例8、9的經染色的人工皮革後,對實施例8、9的經染色的人工皮革分別進行染色力度的量測以及物性測試,其結果如下表3所示。After obtaining the dyed artificial leathers of Examples 8 and 9, the dyeing intensity and physical properties of the dyed artificial leathers of Examples 8 and 9 were measured respectively, and the results are shown in Table 3 below.

[表3]   % o.w.f. L* a* b* K/S 經染色後的人工皮革的顏色 耐水牢度測試   (AATCC 107) 實施例8 5 59.11 2.78 12.29 8.2 棕色 4 實施例9 5 59.31 2.83 11.81 6.9 棕色 4 [table 3] % owf L* a* b* K/S Color of artificial leather after dyeing Water Fastness Test (AATCC 107) Example 8 5 59.11 2.78 12.29 8.2 brown 4 Example 9 5 59.31 2.83 11.81 6.9 brown 4

由上述的評價結果來看,使用本揭露的染料(DHICA)進行染色後的實施例8、9的人工皮革的耐水牢度測試皆為4級,顯示以本揭露的染料所染色獲得的人工皮革具有良好的耐水牢度,符合產業可利用性。此外,在本揭露的染色條件下,實施例8、9的人工皮革的顏色具有棕色色相。From the above evaluation results, the water fastness tests of the artificial leathers of Examples 8 and 9 after dyeing with the dye (DHICA) disclosed in the present disclosure are all grade 4, which shows that the artificial leather dyed with the dye disclosed in the present disclosure It has good water fastness and meets industrial applicability. In addition, under the dyeing conditions of the present disclosure, the artificial leathers of Examples 8 and 9 have a brown hue.

實驗例Experimental example 4:4: 使用包含Use contains DHICADHICA 以及as well as DHIDHI 的染料對尼龍布進行染色dyes for dyeing nylon cloth

< 實施例Example 10>10>

首先,配製包含有90wt%之5,6-二羥基吲哚(DHI)與5,6-二羥基吲哚-2-羧酸(DHICA)作為染料,其中DHI與DHICA的重量比為1:9,接著將染料加入水中,以配製成2% o.w.f.的染液,並將其pH值調整為5。接著,使尼龍布浸於所述染液中,並在反應溫度為105℃、pH值為5的條件下進行染色50分鐘後,於65℃進行皂洗15分鐘,之後以清水清洗並進行乾燥,以得到實施例10的經染色的尼龍布。First, the preparation contains 90wt% of 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA) as dyes, wherein the weight ratio of DHI to DHICA is 1:9 , then add the dye to water to prepare a 2% o.w.f. dye solution, and adjust its pH to 5. Next, immerse the nylon cloth in the dye solution, and dye it at a reaction temperature of 105°C and a pH value of 5 for 50 minutes, then soap it at 65°C for 15 minutes, then wash it with water and dry it. , to obtain the dyed nylon cloth of Example 10.

< 實施例Example 11>11>

使用與實施例10類似的方法進行染色,其差別只在於實施例11中DHI與DHICA的重量比為5:5。Use the method similar to embodiment 10 to carry out dyeing, and its difference is that the weight ratio of DHI and DHICA in embodiment 11 is 5:5.

< 實施例Example 12>12>

使用與實施例10類似的方法進行染色,其差別只在於實施例12中DHI與DHICA的重量比為7:3。Use the method similar to embodiment 10 to carry out dyeing, and its difference is that the weight ratio of DHI and DHICA is 7:3 in embodiment 12.

< 實施例Example 13>13>

使用與實施例10類似的方法進行染色,其差別只在於實施例13中DHI與DHICA的重量比為9:1。Use the method similar to embodiment 10 to carry out dyeing, and its only difference is that the weight ratio of DHI and DHICA in embodiment 13 is 9:1.

在獲得實施例10-13的經染色的尼龍布後,對實施例10-13的經染色的尼龍布分別進行染色力度的量測以及物性測試,其結果如下表4所示。After obtaining the dyed nylon fabrics of Examples 10-13, the dyeing intensity and physical property tests were respectively carried out on the dyed nylon fabrics of Examples 10-13, and the results are shown in Table 4 below.

[表4]   % o.w.f. DHI:DHICA L* a* b* K/S 經染色後的尼龍布的顏色 耐水牢度測試   (AATCC 107) 實施例10 2 1:9 52.11 8.32 20.84 4.3 棕黑色 4-5 實施例11 2 5:5 45.84 7.16 16.09 7.2 棕黑色 4-5 實施例12 2 7:3 27.81 3.21 6.73 13.8 棕黑色 4-5 實施例13 2 9:1 18.64 2.82 1.51 19.5 棕黑色 4 [Table 4] % owf DHI:DHICA L* a* b* K/S The color of dyed nylon cloth Water Fastness Test (AATCC 107) Example 10 2 1:9 52.11 8.32 20.84 4.3 brown black 4-5 Example 11 2 5:5 45.84 7.16 16.09 7.2 brown black 4-5 Example 12 2 7:3 27.81 3.21 6.73 13.8 brown black 4-5 Example 13 2 9:1 18.64 2.82 1.51 19.5 brown black 4

由上述的評價結果來看,使用本揭露的染料(包含DHI及DHICA)進行染色後的實施例10-12的尼龍布的耐水牢度測試皆為4-5級,而實施例13的尼龍布的耐水牢度測試為4級,顯示以本揭露的染料所染色獲得的尼龍布具有良好的耐水牢度,符合產業可利用性。此外,隨著DHI的比例越高,K/S值越高。另外,在本揭露的染色條件下,實施例10-13的尼龍布的顏色具有棕黑色色相。更具體而言,DHI的比例越高,色相越偏向黑色(即深棕黑色),DHICA的比例越高,色相越偏向棕色(即淺棕黑色)。換言之,本揭露的染料可藉由調整DHI與DHICA之間的比例來控制色相。From the above evaluation results, the water fastness test of the nylon fabrics of Examples 10-12 after dyeing using the dyes disclosed in the present disclosure (including DHI and DHICA) are all grades 4-5, while the nylon fabrics of Example 13 The water fastness test is grade 4, which shows that the nylon cloth obtained by dyeing with the dye disclosed in this disclosure has good water fastness, which is in line with industrial applicability. In addition, as the ratio of DHI is higher, the K/S value is higher. In addition, under the dyeing conditions disclosed in the present disclosure, the color of the nylon cloth of Examples 10-13 has a brown-black hue. More specifically, the higher the ratio of DHI, the more black the hue (that is, dark brown-black), and the higher the ratio of DHICA, the more brown the hue (that is, light brown-black). In other words, the dye of the present disclosure can control the hue by adjusting the ratio between DHI and DHICA.

實驗例Experimental example 5:5: 在不同in difference pHpH 值下對尼龍布進行染色Dyeing nylon cloth

< 實施例Example 14>14>

首先,配製包含有90wt%之5,6-二羥基吲哚(DHI)與5,6-二羥基吲哚-2-羧酸(DHICA)作為染料,其中DHI與DHICA的重量比為5:5,接著將染料加入水中,以配製成1% o.w.f.的染液,並將其pH值調整為4.5。接著,使尼龍布浸於所述染液中,並在反應溫度為105℃、pH值為4.5的條件下進行染色50分鐘後,於65℃進行皂洗15分鐘,之後以清水清洗並進行乾燥,以得到實施例14的經染色的尼龍布。First, the preparation contains 90wt% of 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA) as dyes, wherein the weight ratio of DHI to DHICA is 5:5 , then add the dye to water to prepare a 1% o.w.f. dye solution and adjust its pH to 4.5. Next, soak the nylon cloth in the dyeing solution, and dye it at a reaction temperature of 105°C and a pH value of 4.5 for 50 minutes, then soap it at 65°C for 15 minutes, then wash it with water and dry it. , to obtain the dyed nylon cloth of Example 14.

< 實施例Example 15>15>

使用與實施例14類似的方法進行染色,其差別只在於實施例15的染料的pH值為5。Dyeing was carried out using a method similar to Example 14, the only difference being that the pH value of the dye in Example 15 was 5.

< 實施例Example 16>16>

使用與實施例14類似的方法進行染色,其差別只在於實施例16的染料的pH值為6。Dyeing was carried out using a method similar to Example 14, the only difference being that the pH value of the dye in Example 16 was 6.

< 比較例comparative example 1>1>

使用與實施例14類似的方法進行染色,其差別只在於比較例1的染料的pH值為7。Dyeing was performed using a method similar to that of Example 14, the only difference being that the pH value of the dye in Comparative Example 1 was 7.

< 比較例comparative example 2>2>

使用與實施例14類似的方法進行染色,其差別只在於比較例2的染料的pH值為8。Dyeing was performed using a method similar to that of Example 14, the only difference being that the pH value of the dye in Comparative Example 2 was 8.

< 比較例comparative example 3>3>

使用與實施例14類似的方法進行染色,其差別只在於比較例3的染料的pH值為10。Dyeing was performed using a method similar to that of Example 14, the only difference being that the pH value of the dye in Comparative Example 3 was 10.

< 比較例comparative example 4>4>

使用與實施例14類似的方法進行染色,其差別只在於比較例4的染料的pH值為11。Dyeing was performed using a method similar to that of Example 14, the only difference being that the pH value of the dye in Comparative Example 4 was 11.

< 比較例comparative example 5>5>

使用與實施例14類似的方法進行染色,其差別只在於比較例4的染料的pH值為12。Dyeing was carried out using a method similar to that of Example 14, the only difference being that the pH value of the dye in Comparative Example 4 was 12.

在獲得實施例14-16以及比較例1-5的經染色的尼龍布後,對實施例14-16以及比較例1-5的經染色的尼龍布分別進行染色力度的量測以及物性測試,其結果如下表5所示。After obtaining the dyed nylon fabrics of Examples 14-16 and Comparative Examples 1-5, the dyed nylon fabrics of Examples 14-16 and Comparative Examples 1-5 were respectively measured for dyeing strength and physical property tests, The results are shown in Table 5 below.

[表5]   pH值 L* a* b* K/S 耐水牢度測試(AATCC 107) 實施例14 4.5 46.49 7.81 17.34 7.11 4-5 實施例15 5 49.71 7.41 16.70 5.53 4-5 實施例16 6 55.82 7.54 16.61 3.69 4-5 比較例1 7 60.23 7.31 16.71 2.79 4-5 比較例2 8 68.93 3.95 12.32 1.31 4-5 比較例3 10 78.45 2.10 12.45 0.78 4-5 比較例4 11 80.31 1.08 10.42 0.67 4-5 比較例5 12 87.55 -0.46 2.79 0.31 4-5 [table 5] pH value L* a* b* K/S Water Fastness Test (AATCC 107) Example 14 4.5 46.49 7.81 17.34 7.11 4-5 Example 15 5 49.71 7.41 16.70 5.53 4-5 Example 16 6 55.82 7.54 16.61 3.69 4-5 Comparative example 1 7 60.23 7.31 16.71 2.79 4-5 Comparative example 2 8 68.93 3.95 12.32 1.31 4-5 Comparative example 3 10 78.45 2.10 12.45 0.78 4-5 Comparative example 4 11 80.31 1.08 10.42 0.67 4-5 Comparative Example 5 12 87.55 -0.46 2.79 0.31 4-5

由上述的評價結果來看,相較於在中性或鹼性條件下(pH值為7-12)進行染色的比較例1-5,在酸性條件下(pH值為4.5-6)進行染色的實施例14-16的尼龍布,不僅耐水牢度測試可達4-5級,且展現較佳的色深度(K/S值)。From the above evaluation results, dyeing was performed under acidic conditions (pH 4.5-6) compared to Comparative Examples 1-5, which were dyed under neutral or alkaline conditions (pH 7-12). The nylon cloth of Examples 14-16 not only has a water fastness test of 4-5 grades, but also exhibits a better color depth (K/S value).

實驗例Experimental example 6:6: 在不同溫度下對尼龍布進行染色Dyeing nylon cloth at different temperatures

< 實施例Example 17>17>

使用與實施例15類似的方法進行染色,其差別只在於實施例17的反應溫度為85℃。Dyeing was carried out using a method similar to that of Example 15, the only difference being that the reaction temperature of Example 17 was 85°C.

< 實施例Example 18>18>

使用與實施例15類似的方法進行染色,其差別只在於實施例18的反應溫度為95℃。Dyeing was carried out using a method similar to that of Example 15, the only difference being that the reaction temperature of Example 18 was 95°C.

< 實施例Example 19>19>

使用與實施例15類似的方法進行染色,其差別只在於實施例19的反應溫度為115℃。Dyeing was carried out using a method similar to that of Example 15, the only difference being that the reaction temperature of Example 19 was 115°C.

< 實施例Example 20>20>

使用與實施例15類似的方法進行染色,其差別只在於實施例20的反應溫度為125℃。Dyeing was carried out using a method similar to that of Example 15, the only difference being that the reaction temperature of Example 20 was 125°C.

< 比較例comparative example 6>6>

使用與實施例15類似的方法進行染色,其差別只在於比較例6的反應溫度為75℃。Dyeing was performed using a method similar to that of Example 15, the only difference being that the reaction temperature of Comparative Example 6 was 75°C.

在獲得實施例17-20以及比較例6的經染色的尼龍布後,對實施例17-20以及比較例6的經染色的尼龍布分別進行染色力度的量測以及物性測試,其結果如下表6所示。After obtaining the dyed nylon fabrics of Examples 17-20 and Comparative Example 6, the dyed nylon fabrics of Examples 17-20 and Comparative Example 6 were respectively measured for dyeing strength and physical property tests, and the results are shown in the following table 6.

[表6]   反應溫度 (℃) L* a* b* K/S 耐水牢度測試   (AATCC 107) 實施例15 105 49.71 7.41 16.70 5.5 4-5 實施例17 85 53.2 6.6 14.9 3.9 4-5 實施例18 95 52.2 7.6 14.4 4.2 4-5 實施例19 115 48.9 7.0 14.1 5.1 4-5 實施例20 125 50.0 7.0 14.0 4.6 4-5 比較例6 75 60.9 4.9 14.9 2.6 4-5 [Table 6] Reaction temperature (°C) L* a* b* K/S Water Fastness Test (AATCC 107) Example 15 105 49.71 7.41 16.70 5.5 4-5 Example 17 85 53.2 6.6 14.9 3.9 4-5 Example 18 95 52.2 7.6 14.4 4.2 4-5 Example 19 115 48.9 7.0 14.1 5.1 4-5 Example 20 125 50.0 7.0 14.0 4.6 4-5 Comparative example 6 75 60.9 4.9 14.9 2.6 4-5

由上述的評價結果來看,相較於在75℃的反應溫度條件下進行染色的比較例6,在85℃-125℃的反應溫度條件下進行染色的實施例15、17-20的尼龍布,不僅耐水牢度測試可達4-5級,且展現較佳的色深度(K/S值)。From the above evaluation results, compared to Comparative Example 6 dyed at a reaction temperature of 75°C, the nylon fabrics of Examples 15, 17-20 dyed at a reaction temperature of 85°C to 125°C , not only the water fastness test can reach 4-5 grades, but also shows a better color depth (K/S value).

實驗例Experimental example 7:7: 使用包含Use contains DHIDHI 的染料及商用黑色染料對尼龍布進行染色Dyes and commercial black dyes for dyeing nylon cloth

< 實施例Example 21>21>

首先,混合5,6-二羥基吲哚(DHI)以及商用黑色染料(泰鋒染化Oriental Giant Dyes & Chemical,染料名稱:Bestalan Black D-R3)以配置成含有50 wt%之DHI的染料,其中DHI與商用黑色染料的重量比為1:1,接著將混合染料加入水中,以配製成染液(DHI與商用酸性黑色染料在染液中的含量各自為5% o.w.f.),並將其pH值調整為5。接著,使尼龍布浸於所述染液中,並在反應溫度為105℃、pH值為5的條件下進行染色50分鐘後,於65℃進行皂洗15分鐘,之後以清水清洗並進行乾燥,以得到實施例21的經染色的尼龍布。First, mix 5,6-dihydroxyindole (DHI) and a commercial black dye (Oriental Giant Dyes & Chemical, dye name: Bestalan Black D-R3) to prepare a dye containing 50 wt% DHI, The weight ratio of DHI to commercial black dye is 1:1, and then the mixed dye is added to water to prepare a dye solution (the content of DHI and commercial acid black dye in the dye solution is 5% o.w.f.), and the The pH value was adjusted to 5. Next, soak the nylon cloth in the dyeing solution, and dye it at a reaction temperature of 105°C and a pH value of 5 for 50 minutes, then soap it at 65°C for 15 minutes, then wash it with water and dry it. , to obtain the dyed nylon cloth of Example 21.

在獲得實施例21的經染色的尼龍布後,對實施例21的經染色的尼龍布進行染色力度的量測以及物性測試,其結果如下表7所示。After obtaining the dyed nylon cloth of Example 21, the measurement of dyeing strength and the physical property test were carried out on the dyed nylon cloth of Example 21, and the results are shown in Table 7 below.

[表7]   L* a* b* K/S 經染色後的尼龍布的顏色 水洗堅牢度測試 (AATCC 61) 耐水牢度測試   (AATCC 107) 乾、溼摩擦牢度測試   (AATCC 8) 實施例21 12.3 -0.7 -2.1 31.5 黑色 4-5 4-5 4-5 [Table 7] L* a* b* K/S The color of dyed nylon cloth Washing Fastness Test (AATCC 61) Water Fastness Test (AATCC 107) Dry and Wet Rubbing Fastness Test (AATCC 8) Example 21 12.3 -0.7 -2.1 31.5 black 4-5 4-5 4-5

由上述的評價結果來看,使用混合有本揭露的染料(DHI)及商用黑色染料的混合染料進行染色後的實施例21的尼龍布的水洗堅牢度測試、耐水牢度測試、以及乾、溼摩擦牢度測試皆為4-5級,顯示以本揭露的染料可與其他商用染料搭配,且所染色獲得的尼龍布具有良好的水洗堅牢度、耐水牢度、乾、溼摩擦牢度等綜合性能,符合產業可利用性。此外,在本揭露的染色條件下,實施例21的尼龍布的顏色具有黑色色相。Judging from the above evaluation results, the washing fastness test, water fastness test, and dry and wet dyeing of the nylon cloth of Example 21 after dyeing with the dye mixed with the disclosed dye (DHI) and the commercial black dye were carried out. The rubbing fastness tests are all 4-5 grades, showing that the dyes disclosed in this disclosure can be matched with other commercial dyes, and the nylon cloth obtained by dyeing has good washing fastness, water fastness, dry and wet rubbing fastness, etc. performance, in line with industrial availability. In addition, under the dyeing conditions of the present disclosure, the color of the nylon cloth of Example 21 has a black hue.

綜上所述,由於本揭露的染料不以苯胺作為原料,且可用於聚醯胺材料的染色以及有利於低碳製程,因此可有效降低對環境危害與對人類健康風險。In summary, since the dye disclosed herein does not use aniline as a raw material, and can be used for dyeing polyamide materials and is beneficial to low-carbon manufacturing processes, it can effectively reduce environmental hazards and human health risks.

雖然本揭露已以實施例揭露如上,然其並非用以限定本揭露,任何所屬技術領域中具有通常知識者,在不脫離本揭露的精神和範圍內,當可作些許的更動與潤飾,故本揭露的保護範圍當視後附的申請專利範圍所界定者為準。Although the present disclosure has been disclosed above with embodiments, it is not intended to limit the present disclosure. Anyone with ordinary knowledge in the technical field may make some changes and modifications without departing from the spirit and scope of the present disclosure. The scope of protection of this disclosure should be defined by the scope of the appended patent application.

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無。none.

Claims (20)

一種染料,用於對具有醯胺官能基的材料進行染色,所述染料包括: 式(I)表示的化合物;以及 溶劑, (I) 在所述式(I)中,R 1、R 2及R 3各自獨立地為H、-OH或-COOH, 其中R 1、R 2及R 3中的至少一者為-OH或-COOH,且 按所述染料的總重量為100 wt%計,所述式(I)表示的化合物的含量為40 wt%至95 wt%。 A dye for dyeing a material with an amide functional group, the dye comprising: a compound represented by formula (I); and a solvent, (I) In the formula (I), R 1 , R 2 and R 3 are each independently H, -OH or -COOH, wherein at least one of R 1 , R 2 and R 3 is -OH or -COOH, and based on 100 wt% of the total weight of the dye, the content of the compound represented by the formula (I) is 40 wt% to 95 wt%. 如請求項1所述的染料,其中所述式(I)表示的化合物由化學合成或生物合成而得。The dye as claimed in item 1, wherein the compound represented by the formula (I) is obtained by chemical synthesis or biological synthesis. 如請求項1所述的染料,其中所述式(I)表示的化合物包括5,6-二羥基吲哚(5,6-dihydroxyindole;DHI)、5,6-二羥基吲哚-2-羧酸(5,6-dihydroxyindole-2-carboxylic acid;DHICA)或前述之組合。The dye as claimed in item 1, wherein the compound represented by the formula (I) includes 5,6-dihydroxyindole (5,6-dihydroxyindole; DHI), 5,6-dihydroxyindole-2-carboxy Acid (5,6-dihydroxyindole-2-carboxylic acid; DHICA) or a combination of the foregoing. 如請求項1所述的染料,其中所述具有醯胺官能基的材料包括尼龍、人工皮革或前述之組合。The dye according to claim 1, wherein the material having amide functional groups includes nylon, artificial leather or a combination thereof. 如請求項1所述的染料,其中所述染料包括5,6-二羥基吲哚以及5,6-二羥基吲哚-2-羧酸,且5,6-二羥基吲哚與5,6-二羥基吲哚-2-羧酸的重量比為1:15至15:1。The dye as claimed in item 1, wherein the dye includes 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid, and 5,6-dihydroxyindole and 5,6 - Dihydroxyindole-2-carboxylic acid in a weight ratio of 1:15 to 15:1. 如請求項1所述的染料,其中由所述染料所染出的色相為黑色、棕色或兩者的混合色。The dye as claimed in item 1, wherein the hue dyed by the dye is black, brown or a mixed color of the two. 如請求項1所述的染料,其中所述染料的pH值為3.5-6.5。The dye as claimed in item 1, wherein the pH of the dye is 3.5-6.5. 一種染色方法,包括使用染液與具有醯胺官能基的材料接觸,以進行染色步驟,其中所述染液包括包含式(I)表示的化合物的染料, (I) 在所述式(I)中,R 1、R 2及R 3各自獨立地為H、-OH或-COOH, 其中R 1、R 2及R 3中的至少一者為-OH或-COOH,且 按所述染料的總重量為100 wt%計,所述式(I)表示的化合物的含量為40 wt%至95 wt%。 A dyeing method, comprising using a dye solution to contact a material with an amide functional group to carry out a dyeing step, wherein the dye solution includes a dye comprising a compound represented by formula (I), (I) In the formula (I), R 1 , R 2 and R 3 are each independently H, -OH or -COOH, wherein at least one of R 1 , R 2 and R 3 is -OH or -COOH, and based on 100 wt% of the total weight of the dye, the content of the compound represented by the formula (I) is 40 wt% to 95 wt%. 如請求項8所述的染色方法,其中所述式(I)表示的化合物包括5,6-二羥基吲哚(5,6-dihydroxyindole;DHI)、5,6-二羥基吲哚-2-羧酸(5,6-dihydroxyindole-2-carboxylic acid;DHICA)或前述之組合。The dyeing method as claimed in item 8, wherein the compound represented by the formula (I) includes 5,6-dihydroxyindole (5,6-dihydroxyindole; DHI), 5,6-dihydroxyindole-2- Carboxylic acid (5,6-dihydroxyindole-2-carboxylic acid; DHICA) or a combination of the foregoing. 如請求項8所述的染色方法,其中所述具有醯胺官能基的材料包括尼龍、人工皮革或前述之組合。The dyeing method as claimed in claim 8, wherein the material having amide functional groups includes nylon, artificial leather or a combination thereof. 如請求項8所述的染色方法,所述染液中的所述染料的濃度為1%對織物重(on weight of the fabric,o.w.f.)至25%對織物重。The dyeing method as claimed in item 8, the concentration of the dye in the dye liquor is 1% on weight of the fabric (o.w.f.) to 25% on weight of the fabric. 如請求項8所述的染色方法,其中所述染料包括5,6-二羥基吲哚以及5,6-二羥基吲哚-2-羧酸,且5,6-二羥基吲哚與5,6-二羥基吲哚-2-羧酸的重量比為1:15至15:1。The dyeing method as claimed in item 8, wherein the dye includes 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid, and 5,6-dihydroxyindole and 5, The weight ratio of 6-dihydroxyindole-2-carboxylic acid is from 1:15 to 15:1. 如請求項8所述的染色方法,其中經染色後的所述具有醯胺官能基的材料的色相為黑色、棕色或兩者的混合色。The dyeing method as claimed in item 8, wherein the hue of the dyed material having an amide functional group is black, brown or a mixed color of the two. 如請求項8所述的染色方法,其中所述染色步驟的反應溫度在80℃至130℃下進行。The dyeing method as claimed in item 8, wherein the reaction temperature of the dyeing step is carried out at 80°C to 130°C. 如請求項8所述的染色方法,所述染色步驟的反應pH值為3.5至6.5。The dyeing method as claimed in item 8, the reaction pH value of the dyeing step is 3.5 to 6.5. 如請求項8所述的染色方法,所述染色步驟的反應時間為30分鐘至60分鐘。The dyeing method as claimed in item 8, the reaction time of the dyeing step is 30 minutes to 60 minutes. 如請求項8所述的染色方法,經染色後的所述具有醯胺官能基的材料的乾濕摩擦牢度測試(AATCC 8)為4至5級。According to the dyeing method described in claim item 8, the dry and wet rubbing fastness test (AATCC 8) of the dyed material having amide functional groups is grade 4 to 5. 如請求項8所述的染色方法,經染色後的所述具有醯胺官能基的材料的耐水牢度測試(AATCC 107)為4至5級。According to the dyeing method described in claim item 8, the water fastness test (AATCC 107) of the dyed material having amide functional groups is grade 4 to 5. 如請求項8所述的染色方法,經染色後的所述具有醯胺官能基的材料的水洗堅牢度測試(AATCC 61)為4至5級。According to the dyeing method described in claim item 8, the washing fastness test (AATCC 61) of the dyed material having amide functional groups is grade 4 to 5. 如請求項8所述的染色方法,經染色後的所述具有醯胺官能基的材料的K/S值為3至35。According to the dyeing method described in Claim 8, the K/S value of the dyed material having amide functional groups is 3 to 35.
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