TWI682005B - High fastness disperse black dye composition - Google Patents

High fastness disperse black dye composition Download PDF

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TWI682005B
TWI682005B TW107104578A TW107104578A TWI682005B TW I682005 B TWI682005 B TW I682005B TW 107104578 A TW107104578 A TW 107104578A TW 107104578 A TW107104578 A TW 107104578A TW I682005 B TWI682005 B TW I682005B
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formula
component
fastness
compound
dye
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TW201915098A (en
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李百春
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大陸商杭州福萊蒽特精細化工有限公司
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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
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008—Preparations of disperse dyes or solvent dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B51/00—Nitro or nitroso dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/022—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring the heterocyclic ring being alternatively specified
    • C09B62/026—Azo dyes
    • C09B62/028—Monoazo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/022—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring the heterocyclic ring being alternatively specified
    • C09B62/034—Nitro dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • 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
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D06P1/19—Nitro dyes

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

Abstract

The present invention discloses a high fastness disperse black dye composition including component A, component B, component C and component D. Component A is selected from at least one of the compounds of formula (I). Component B is selected from at least one of the compounds of formula (II). Component C is selected from at least one of the compounds of formula (III) and/or formula (IV). Component D is selected from at least one of the compounds of formula (V). The high fastness disperse black dye composition provided by the invention has the characteristics of environmental protection, clean process and high product fastness when applied.

Description

高牢度分散黑色染料組合物High-fastness disperse black dye composition

本發明涉及分散染料領域，特別涉及一種高牢度分散黑色染料組合物。The invention relates to the field of disperse dyes, in particular to a high-fastness disperse black dye composition.

中國大陸是染料、紡織品生產大國，黑色染料在紡織印染、皮革等領域，佔有舉足輕重的地位。Mainland China is a major producer of dyes and textiles. Black dyes play an important role in textile printing and leather.

早期黑色染料主要是有聯苯胺衍生的偶氮染料，具有烏黑度好、上染率高等優點，但在生產中與使用中會釋放出致癌中間體聯苯胺；為此，20世紀70年代由聯苯胺衍生的所有直接和酸性品種的黑色染料相繼被禁用。開發染色性能有意的新型非誘變性環保黑色染料已成為一項具有重大意義的課題。目前已成功合成出大量的新品種黑色染料，且提高黑色染料使用性能的染料複配技術也獲得一定突破。複配性分散染料是指色相接近或性能接近，化學結構答題相近或不同的分散染料的混合物，但不包括染料合成過程中產生的異構體。一般是兩個以上的多組分，組分之間有一定比例。The early black dyes were mainly azo dyes derived from benzidine, which had the advantages of good blackness and high dyeing rate. However, in the production and use, the carcinogenic intermediate benzidine was released; All direct and acidic black dyes derived from aniline have been banned. The development of new non-mutagenic environmentally friendly black dyes with intentional dyeing properties has become a topic of great significance. At present, a large number of new black dyes have been successfully synthesized, and the dye compounding technology to improve the performance of black dyes has also achieved certain breakthroughs. Compound disperse dyes refer to mixtures of disperse dyes with similar hue or performance, similar chemical structure or similar answers, but does not include isomers produced during dye synthesis. Generally it is more than two multi-components, and there is a certain ratio between the components.

中國大陸分散染料的商品化質量存在不少問題，比如粒徑大、粒徑分佈範圍寬、離子形狀不規則、染料的晶型不穩定、分散穩定性差；比較突出的問題是耐熱遷移性差，耐摩擦、耐水洗牢度低，難以達到AATCC（美國染化師協會）等國際標準。且從已有的複配染料來看，其染色配伍性和重現性等應用性能仍不能完全滿足要求。There are many problems in the commercial quality of disperse dyes in mainland China, such as large particle size, wide particle size distribution range, irregular ion shape, unstable crystal form of the dye, and poor dispersion stability; the more prominent problems are poor heat resistance and resistance The friction and washing fastness are low, and it is difficult to meet the international standards such as AATCC (American Association of Dyeing and Chemical Engineers). And from the point of view of the existing compound dyes, its application properties such as dye compatibility and reproducibility still cannot fully meet the requirements.

本發明所要解決的技術問題在於提供一種健康環保，工藝清潔高牢度分散黑色染料組合物，該高牢度分散黑色染料組合物還具有環保標準高特點。The technical problem to be solved by the present invention is to provide a healthy and environmentally friendly, process-cleaning high-fastness dispersed black dye composition, which also has high environmental protection standard characteristics.

為了實現上述發明目的，本發明提供如下技術方案：In order to achieve the above object of the invention, the present invention provides the following technical solutions:

一種高牢度分散黑色染料組合物，包括組分A、組分B、組分C和組分D，其中組分A選自式（I）所示化合物中的至少一種，組分B選自式（II）所示化合物中的至少一種，所述的組分D選自式（V）所示化合物中的至少一種所述的組分C選自式（III）和/或式（IV）所示化合物中的至少一種。式（I）～（V）具有如下結構：

Figure 02_image001
A high-fastness dispersed black dye composition, including component A, component B, component C and component D, wherein component A is selected from at least one of the compounds represented by formula (I), component B is selected from At least one of the compounds represented by the formula (II), the component D is selected from the compounds represented by the formula (V), and at least one of the component C is selected from the formula (III) and/or formula (IV) At least one of the compounds shown. Formulas (I) to (V) have the following structure:
Figure 02_image001

式（I）中R1 為氫或C1～C4的烷氧基，優選為甲氧基或乙氧基；R2 、R3 各自獨立地選自C1～C4的烷基；m、n各自獨立地選自1、2、3或4。

Figure 02_image003
In formula (I), R 1 is hydrogen or C1-C4 alkoxy, preferably methoxy or ethoxy; R 2 and R 3 are each independently selected from C1-C4 alkyl; m and n are independently Ground is selected from 1, 2, 3 or 4.
Figure 02_image003

式（II）中R4 為氫或鹵素，優選為氯或溴。

Figure 02_image005
Figure 02_image007
In formula (II), R 4 is hydrogen or halogen, preferably chlorine or bromine.
Figure 02_image005
Figure 02_image007

式（III）和式（IV）中，R5 、R6 、R7 、R8 各自獨立地選自C1～C4的烷基，各自獨立地優選為甲基。

Figure 02_image009
In formula (III) and formula (IV), R 5 , R 6 , R 7 , and R 8 are each independently selected from C1 to C4 alkyl groups, and each independently is preferably a methyl group.
Figure 02_image009

式（V）中，R9 選自C1～C4的烷基，優選為甲基或乙基；R10 選自C1～C4的烷氧基，優選為甲氧基或乙氧基。所述組份D優選包含式（V）中R7 為甲基和乙基的化合物，且甲基:乙基=1:1或者所述組分D中優選包含式（V）中R7 為乙基和異丙氧基丙基的化合物，且含有乙基: 異丙氧基丙基=2:1。In formula (V), R 9 is selected from C1-C4 alkyl, preferably methyl or ethyl; R 10 is selected from C1-C4 alkoxy, preferably methoxy or ethoxy. The component D preferably comprises a compound of formula (V) where R 7 is methyl and ethyl, and methyl:ethyl=1:1 or the component D preferably comprises R 7 of formula (V) Ethyl and isopropyloxypropyl compounds, and contains ethyl: isopropyloxypropyl = 2:1.

本發明中，所述的C1～C4烷基可以是甲基、乙基、正丙基、異丙基、正丁基、異丁基、叔丁基等，所述的C1～C4烷氧基可以是甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、叔丁氧基等，所述的鹵素可以是氟、氯、溴或碘；所述Ac為乙醯基。In the present invention, the C1-C4 alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. The C1-C4 alkoxy group It may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, etc. The halogen may be fluorine, chlorine, bromine or iodine; The Ac is acetyl.

優選地，組分A的重量百分含量為10～30％，組分B的重量百分含量為10～20％，組分C的重量百分含量為1～10％，組分D的重量百分含量為3～15％，餘量為助劑。Preferably, the weight percentage of component A is 10-30%, the weight percentage of component B is 10-20%, the weight percentage of component C is 1-10%, and the weight of component D The percentage content is 3 to 15%, and the balance is auxiliary.

更優選地，組分A的重量百分含量為10～20％（如14%），組分B的重量百分含量為12～16％（如13%），組分C的重量百分含量為2～5％（如3%），組分D的重量百分含量為5～10％（如7%），餘量為助劑。More preferably, the weight percentage of component A is 10-20% (such as 14%), the weight percentage of component B is 12-16% (such as 13%), and the weight percentage of component C is It is 2 to 5% (such as 3%), the weight percentage content of component D is 5 to 10% (such as 7%), and the balance is auxiliary.

作為優選的，所述染料組分A優選自下式（I-1）～（I-9）所示染料化合物中的至少一種：

Figure 02_image011
Figure 02_image013
Figure 02_image015
Figure 02_image017
Figure 02_image019
Figure 02_image021
Figure 02_image023
Figure 02_image025
Figure 02_image027
Preferably, the dye component A is preferably at least one of the dye compounds represented by the following formulas (I-1) to (I-9):
Figure 02_image011
Figure 02_image013
Figure 02_image015
Figure 02_image017
Figure 02_image019
Figure 02_image021
Figure 02_image023
Figure 02_image025
Figure 02_image027

優選的，所述染料組分B優選自下式（II-1）～（II-3）所示染料化合物中的至少一種：

Figure 02_image029
Figure 02_image031
Figure 02_image033
Preferably, the dye component B is preferably at least one of the dye compounds represented by the following formulas (II-1) to (II-3):
Figure 02_image029
Figure 02_image031
Figure 02_image033

作為優選的，所述染料組分C優選自下式（III-1）～（III-3）、（IV-1）～（IV-3）所示染料化合物中的至少一種：

Figure 02_image035
Figure 02_image037
Figure 02_image039
Figure 02_image041
Figure 02_image043
Figure 02_image045
。Preferably, the dye component C is preferably at least one of the dye compounds represented by the following formulas (III-1) to (III-3) and (IV-1) to (IV-3):
Figure 02_image035
Figure 02_image037
Figure 02_image039
Figure 02_image041
Figure 02_image043
Figure 02_image045
.

作為優選的，所述染料組分D優選自下式（V-1）～（V-6）所示染料化合物中的至少一種：

Figure 02_image047
Figure 02_image049
Figure 02_image051
Figure 02_image053
Figure 02_image055
Figure 02_image057
。Preferably, the dye component D is preferably at least one of the dye compounds represented by the following formulas (V-1) to (V-6):
Figure 02_image047
Figure 02_image049
Figure 02_image051
Figure 02_image053
Figure 02_image055
Figure 02_image057
.

本發明所述的高牢度分散黑色染料組合物，作為商品出售或應用於紡織材料著色時，通常還需要加入助劑進行處理。本發明所述的助劑為分散染料複配時常用的分散劑、擴散劑及其它表面活性劑等，優選自下列之一或其中兩種以上的混合物：木質素磺酸鹽、烷基萘磺酸甲醛縮合物、萘磺酸甲醛縮合物、苄基萘磺酸甲醛縮合物等。When the high-fastness dispersed black dye composition described in the present invention is sold as a commercial product or used for coloring textile materials, it is usually necessary to add additives for processing. The auxiliary agent described in the present invention is a dispersant, a diffusing agent and other surfactants commonly used in the formulation of disperse dyes, preferably one or a mixture of two or more of the following: lignin sulfonate, alkyl naphthalene sulfonate Acid formaldehyde condensate, naphthalenesulfonic acid formaldehyde condensate, benzyl naphthalenesulfonic acid formaldehyde condensate, etc.

所述木質素磺酸鹽，具體地可以為木質素磺酸鈉，更具體地為木質素85A或木質素83A；所述烷基萘磺酸甲醛縮合物，可以為甲基萘磺酸甲醛縮合物，例如分散劑MF；所述萘磺酸甲醛縮合物，可以為擴散劑NNO等，所述苄基萘磺酸甲醛縮合物，具體地可以為擴散劑CNF。The lignin sulfonate may specifically be sodium lignin sulfonate, more specifically lignin 85A or lignin 83A; the alkyl naphthalene sulfonate formaldehyde condensate may be methyl naphthalene sulfonate formaldehyde condensation For example, the dispersant MF; the naphthalenesulfonic acid formaldehyde condensate may be a diffusing agent NNO and the like, and the benzylnaphthalenesulfonic acid formaldehyde condensate may specifically be a diffusing agent CNF.

本發明中，式（I）～（V）所示的染料化合物可方便地按本領域技術人員熟知的方式合成，也可以採用市售商品。In the present invention, the dye compounds represented by formulae (I) to (V) can be conveniently synthesized in a manner well known to those skilled in the art, or commercially available products can also be used.

本發明的分散染料組合物，應用於染色時可以按如下方法進行：The disperse dye composition of the present invention can be applied as follows when applied to dyeing:

將分散黑染料組合物的染料單體化合物按配比混合後，在助劑、水的存在下用砂磨機或研磨機等粉碎機進行微粒子化，也可以將染料單體化合物分別在助劑、水的存在下用砂磨機或研磨機等粉碎機進行微粒子化處理後按比例進行混合。本發明所述的分散紅染料製品，用砂磨機或研磨機研磨後為液狀，噴霧乾燥後可為粉狀、顆粒狀，這是本領域技術人員公知的製備方法，由於噴霧乾燥過程中不可能將水分100％的脫除，因此即便是粉狀或顆粒狀的染料製品中，仍允許存在一定量的水分，優選不超過染料製品總重的12%。After mixing the dye monomer compounds of the disperse black dye composition according to the ratio, in the presence of an auxiliary agent and water, the particles are micronized with a grinder such as a sand mill or a grinder. In the presence of water, the particles are treated with a grinder such as a sand mill or grinder, and then mixed in proportion. The disperse red dye product according to the present invention is liquid after being ground with a sand mill or grinder, and can be powdered or granulated after spray drying. This is a preparation method known to those skilled in the art. It is impossible to remove 100% of water, so even in powder or granular dye products, a certain amount of moisture is still allowed, preferably not more than 12% of the total weight of the dye product.

利用本發明的染料組合物製成的染料，可按行業內慣用方式對疏水性纖維材料（如聚酯及其混紡交織物）進行染色，如採用普通浸染法或高溫高壓染色法進行染色，也可用於直接印花。其中，普通浸染法如將疏水性纖維材料進行預處理，放入染缸中進行浸染，染畢，冷水清洗至中性，絞乾，再進行還原清洗，烘乾；直接印花如將織物進行染前處理，烘乾，定形，在印花機上印分散染料色漿，再進行蒸化，利用汽蒸方式使織物上的染料固色，最後水洗，拉幅定型。The dyes made by the dye composition of the present invention can be used to dye hydrophobic fiber materials (such as polyester and its blended cross-woven fabrics) in the usual way in the industry, such as ordinary dip dyeing or high temperature and high pressure dyeing. Can be used for direct printing. Among them, the common dip dyeing method is to pre-treat the hydrophobic fiber material, put it into a dyeing tank for dip dyeing, dyeing is completed, cold water is washed to neutral, wrung, then reduced cleaning, drying; direct printing is like dyeing the fabric before Treatment, drying, setting, printing the disperse dye paste on the printing machine, then steaming, using steaming to fix the dye on the fabric, finally washing, tenter setting.

隨著滌綸纖維超細化程度越來越高， 對纖維的染深性越來越難， 而且要滿足各項牢度。本高牢度分散黑色染料很好的滿足的染料的染深性， 而且驚奇的發現， 本染料對於滌綸超細纖維和滌綸超細纖維交織如滌綸氨綸， 滌綸尼龍， 滌綸棉，滌綸黏膠等交織染色後，水洗牢度均達到AATCC61IIA 4級以上 ， 昇華牢度180℃30秒 4級以上 ， 日曬牢度60小時4級以上，乾濕摩擦牢度4級以上。As the degree of ultra-fine polyester fiber becomes higher and higher, the dyeing depth of the fiber becomes more and more difficult, and it must meet various fastnesses. This high-fastness dispersed black dye satisfies the dyeing depth of the dye very well, and was surprised to find that this dye interweaves polyester ultrafine fibers and polyester ultrafine fibers such as polyester spandex, polyester nylon, polyester cotton, polyester viscose, etc. After interweaving and dyeing, the washing fastness reached AATCC61IIA level 4 or higher, sublimation fastness 180°C 30 seconds level 4 or higher, sunlight fastness 60 hours level 4 or higher, dry and wet rubbing fastness level 4 or higher.

本高牢度分散黑色染料，滿足了最嚴苛的BLUE signing（ 藍標） 環保認證一類標， 滿足了多氯苯酚， 有機氯載體， 多環芳香烴環保要求的一類標。This high-fastness disperse black dye meets the most stringent BLUE signing (blue label) environmental certification class 1 standard, and meets the environmental requirements of polychlorophenol, organic chlorine carrier, and polycyclic aromatic hydrocarbons.

本高牢度分散黑色染料推動環保節能減排的應用， 此染料在印染廠實際應用過程中，無須還原清洗就可以滿足市場訂單的要求， 減少了印染工廠由於還原清洗帶來的大量廢水，和大量蒸汽使用！是清潔染色的重要染料。This high-fastness dispersed black dye promotes the application of environmental protection, energy saving and emission reduction. In the actual application process of this dyeing plant, it can meet the requirements of market orders without reductive cleaning, reducing the large amount of wastewater caused by reductive cleaning in printing and dyeing factories, and Use a lot of steam! It is an important dye for clean dyeing.

下面對本發明實施例中的技術方案進行清楚、完整地描述，顯然，所描述的實施例僅僅是本發明一部分實施例，而不是全部的實施例。基於本發明中的實施例，本領域普通技術人員在沒有做出創造性勞動的前提下所獲得的所有其他實施例，都屬於本發明保護的範圍。The following clearly and completely describes the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, but not all the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by a person of ordinary skill in the art without creative efforts shall fall within the protection scope of the present invention.

[實施例1][Example 1]

將26克式（I-1）化合物，11克式（II-1）化合物，3克式（III-1）化合物，6克式（V-1）化合物，54克的分散劑MF，加200克水混拼後，研磨分散，噴霧乾燥，即得成品。Add 26 grams of compound of formula (I-1), 11 grams of compound of formula (II-1), 3 grams of compound of formula (III-1), 6 grams of compound of formula (V-1), 54 grams of dispersant MF, add 200 After mixing with water, grind and disperse and spray dry to get the finished product.

[實施例2][Example 2]

將26克式（I-2）化合物，11克式（II-2）化合物，3克式（III-2）化合物，6克式（V-2）化合物，54克的分散劑MF，加200克水混拼後，研磨分散，噴霧乾燥，即得成品。Add 26 grams of compound of formula (I-2), 11 grams of compound of formula (II-2), 3 grams of compound of formula (III-2), 6 grams of compound of formula (V-2), 54 grams of dispersant MF, add 200 After mixing with water, grind and disperse and spray dry to get the finished product.

[實施例3][Example 3]

將26克式（I-5）化合物，11克式（II-1）化合物，3克式（IV-1）化合物，莫耳比1:1為的6克式（V-1）和（V-2）化合物，54克的分散劑MF，加200克水混拼後，研磨分散，噴霧乾燥，即得成品。26 grams of compound of formula (I-5), 11 grams of compound of formula (II-1), 3 grams of compound of formula (IV-1), molar ratio 1:1 is 6 grams of formula (V-1) and (V -2) Compound, 54g of dispersant MF, mixed with 200g of water, grinded and dispersed, spray dried to obtain finished product.

[實施例4][Example 4]

將26克式（I-1）化合物，11克式（II-1）化合物，3克式（III-1）化合物，莫耳比1:1為的6克式（V-1）和（V-2）化合物，54克的分散劑MF，加200克水混拼後，研磨分散，噴霧乾燥，即得成品。26 grams of compound of formula (I-1), 11 grams of compound of formula (II-1), 3 grams of compound of formula (III-1), molar ratio 1:1 is 6 grams of formula (V-1) and (V -2) Compound, 54g of dispersant MF, mixed with 200g of water, grinded and dispersed, spray dried to obtain finished product.

[實施例5][Example 5]

將26克式（I-1）化合物，11克式（II-1）化合物，3克式（III-1）化合物，莫耳比1:1為的6克式（V-4）和（V-5）化合物，54克的分散劑MF，加200克水混拼後，研磨分散，噴霧乾燥，即得成品。26 grams of compound of formula (I-1), 11 grams of compound of formula (II-1), 3 grams of compound of formula (III-1), molar ratio 1:1 is 6 grams of formula (V-4) and (V -5) Compound, 54g of dispersant MF, mixed with 200g of water, grinded and dispersed, spray dried to obtain finished product.

[實施例6][Example 6]

將26克式（I-1）化合物，11克式（II-1）化合物，3克式（III-1）化合物，莫耳比2:1為的6克式（V-2）和式（V-3）化合物，54克的分散劑MF，加200克水混拼後，研磨分散，噴霧乾燥，即得成品。26 grams of compound of formula (I-1), 11 grams of compound of formula (II-1), 3 grams of compound of formula (III-1), a molar ratio of 2:1 to 6 grams of formula (V-2) and formula ( V-3) Compound, 54 g of dispersant MF, mixed with 200 g of water, ground and dispersed, spray-dried to obtain the finished product.

[實施例7][Example 7]

將22克式（I-3）化合物，16克式（II-3）化合物，3克式（III-2）化合物，莫耳比2:1為的8克式（V-5）和式（V-6）化合物，51克的分散劑MF，加200克水混拼後，研磨分散，噴霧乾燥，即得成品。Combine 22 grams of compound of formula (I-3), 16 grams of compound of formula (II-3), 3 grams of compound of formula (III-2), and a molar ratio of 2:1 to 8 grams of formula (V-5) and formula ( V-6) Compound, 51 g of dispersant MF, after adding 200 g of water to mix, grind and disperse, spray-dry to obtain the finished product.

[實施例8][Example 8]

將26克式（I-5）化合物，11克式（II-1）化合物，3克式（IV-1）化合物，莫耳比2:1為的6克式（V-2）和（V-3）化合物，54克的分散劑MF，加200克水混拼後，研磨分散，噴霧乾燥，即得成品。26 grams of compound of formula (I-5), 11 grams of compound of formula (II-1), 3 grams of compound of formula (IV-1), a molar ratio of 2:1 to 6 grams of formula (V-2) and (V -3) Compound, 54g of dispersant MF, mixed with 200g of water, grinded and dispersed, spray dried to obtain finished product.

[實施例9][Example 9]

將26克式（I-7）化合物，11克式（II-2）化合物，3克式（IV-1）化合物，莫耳比2:1為的6克式（V-5）和式（V-6）化合物，54克的分散劑MF，加200克水混拼後，研磨分散，噴霧乾燥，即得成品。26 grams of the compound of formula (I-7), 11 grams of the compound of formula (II-2), 3 grams of the compound of formula (IV-1), a molar ratio 2:1 of 6 grams of formula (V-5) and formula (V-5) V-6) Compound, 54g of dispersant MF, mixed with 200g of water, ground and dispersed, spray-dried to obtain the finished product.

[實施例10～20][Examples 10 to 20]

按照實施例1所述的方法，不同的是採用表1中組分A、組分B、組分C、組分D的重量比以及分散劑MF，其中組分D兩種化合物的比例為莫耳比，加水拼混後製成漿液，控制漿液的含固量為30～40％為宜，研磨分散，乾燥，製得成品。 表1

Figure 107104578-A0304-0001
According to the method described in Example 1, the difference is that the weight ratio of component A, component B, component C, component D and dispersant MF in Table 1 are used, wherein the ratio of the two compounds of component D is The ear ratio is mixed with water to make a slurry. It is suitable to control the solid content of the slurry to 30-40%. Grind and disperse and dry to obtain a finished product. Table 1
Figure 107104578-A0304-0001

[染色實施例1][Dyeing Example 1]

將上述實施例1～21中製得的分散染料，採用常規高溫高壓染色法處理超細化滌綸、滌綸氨綸，滌綸尼龍，滌綸棉，滌綸黏膠等交織物，處理過程中，控制染色深度（o .w .f） 4 .0％以上，浴比1：40，調染浴pH值4～5，室溫入染，升溫至130℃，保溫45min，水洗、乾燥，冷卻到70℃取出。觀察樣布色光，以染色滌綸布樣為例檢測其中多氯苯酚，有機氯載體，多環芳香烴的含量，具體如表2所示。 表2

Figure 107104578-A0304-0002
The disperse dyes prepared in the above Examples 1 to 21 are treated with conventional high-temperature and high-pressure dyeing methods for superfine polyester, polyester spandex, polyester nylon, polyester cotton, polyester viscose and other interwoven fabrics. During the process, the dyeing depth is controlled ( o .w .f) 4.0% or more, bath ratio 1:40, pH value of dyeing bath 4~5, dyeing at room temperature, heating to 130°C, holding 45min, washing with water, drying, cooling to 70°C and taking out. Observe the shade of the sample fabric and take the dyed polyester fabric sample as an example to detect the content of polychlorophenol, organic chlorine carrier and polycyclic aromatic hydrocarbon, as shown in Table 2. Table 2
Figure 107104578-A0304-0002

從相對於對比例染料，本發明的黑色染料均滿足了最嚴苛的BLUE signing（ 藍標） 環保認證一類標，滿足了多氯苯酚，有機氯載體，多環芳香烴環保要求的一類標。With respect to the comparative dyes, the black dyes of the present invention all meet the most stringent BLUE signing (blue label) environmental certification certification standards, and meet the requirements of polychlorophenol, organic chlorine carrier, and polycyclic aromatic hydrocarbons.

對滌綸超細纖維和滌綸超細纖維交織如滌綸氨綸，滌綸尼龍，滌綸棉，滌綸黏膠等交織染色後，採用國際標準ISO105-X12、ISO105-C10、ISO105-X11分別測試其耐摩擦幹濕牢度、耐水洗、耐日曬60小時，耐昇華180℃30秒的色牢度，具體見表3-7。 表3滌綸染色牢度測試

Figure 107104578-A0304-0003
表4 滌綸氨染色牢度測試
Figure 107104578-A0304-0004
 表5 滌綸尼龍染色牢度測試
Figure 107104578-A0304-0005
 表6 滌綸棉染色牢度測試
Figure 107104578-A0304-0006
 表7 滌綸黏膠染色牢度測試
Figure 107104578-A0304-0007
 After interweaving polyester microfibers and polyester microfibers such as polyester spandex, polyester nylon, polyester cotton, polyester viscose, etc., the international standards ISO105-X12, ISO105-C10, ISO105-X11 are used to test their resistance to dry and wet friction. The color fastness to fastness, washing resistance, and sunlight resistance for 60 hours and sublimation resistance at 180℃ for 30 seconds are shown in Table 3-7. Table 3 Test of polyester dyeing fastness
Figure 107104578-A0304-0003
 Table 4 Polyester ammonia dyeing fastness test
Figure 107104578-A0304-0004
 Table 5 Polyester nylon dyeing fastness test
Figure 107104578-A0304-0005
 Table 6 Polyester cotton dyeing fastness test
Figure 107104578-A0304-0006
 Table 7 Dyeing fastness test of polyester viscose
Figure 107104578-A0304-0007

表3-7結果表明，本發明分散染料的各項牢度性能優良，對於滌綸超細纖維和滌綸超細纖維交織如滌綸氨綸，滌綸尼龍，滌綸棉，滌綸黏膠等交織染色後，水洗牢度均達到AATCC61IIA 4級以上，昇華牢度180℃30秒 4級以上，日曬牢度60小時4級以上，乾濕摩擦牢度4級以上。The results of Table 3-7 show that the fastness properties of the disperse dyes of the present invention are excellent. For interweaving polyester ultrafine fibers and polyester ultrafine fibers such as polyester spandex, polyester nylon, polyester cotton, polyester viscose, etc., they are washed fast All of them have reached AATCC61IIA level 4 or higher, sublimation fastness 180℃30 seconds level 4 or higher, sunlight fastness 60 hours level 4 or higher, dry and wet rubbing fastness level 4 or higher.

特別是實施例3-18，其中組分所述組份D優選包含式（V）中R7為甲基和乙基的化合物，且甲基:乙基=1:1或者所述組分D中優選包含式（V）中R7為乙基和異丙氧基丙基的化合物，且含有乙基: 異丙氧基丙基=2:1，其各項牢度基本上均達到5級。In particular, examples 3-18, wherein component D of the component preferably comprises a compound of formula (V) wherein R7 is methyl and ethyl, and methyl:ethyl=1:1 or in component D It is preferred to include a compound of formula (V) in which R7 is ethyl and isopropoxypropyl, and contains ethyl: isopropoxypropyl=2:1, each of which has a fastness of up to level 5.

此外，本發明高牢度分散黑色染料無須還原清洗就可以滿足市場訂單的要求， 減少了印染工廠由於還原清洗帶來的大量廢水，和大量蒸汽使用，推動了環保節能減排。In addition, the high-fastness dispersed black dye of the present invention can meet the requirements of market orders without reductive cleaning, reducing a large amount of waste water and a large amount of steam usage caused by reductive cleaning in printing and dyeing factories, and promoting environmental protection, energy saving and emission reduction.

上述說明已經充分揭露了本發明的具體實施方式。需要指出的是，熟悉該領域的技術人員對本發明的具體實施方式所做的任何改動均不脫離本發明的請求項的範圍。相應地，本發明的請求項的範圍也並不僅僅局限於前述具體實施方式。The above description has fully disclosed the specific embodiments of the present invention. It should be noted that any changes made by those skilled in the art to the specific implementation of the present invention will not deviate from the scope of the claims of the present invention. Accordingly, the scope of the claims of the present invention is not limited to the foregoing specific embodiments.

Claims (9)

一種高牢度分散黑色染料組合物，包括組分A、組分B、組分C和組分D，其中組分A選自式(I)所示化合物中的至少一種，組分B選自式(II)所示化合物中的至少一種，組分C選自式(III)和/或式(IV)所示化合物中的至少一種，組分D選自式(V)所示化合物中的至少一種，式(I)~(V)具有如下結構：
Figure 107104578-A0305-02-0022-1
 (I)中R1為氫或C1~C4的烷氧基，R2、R3各自獨立地選自C1~C4的烷基，m、n各自獨立地選自1、2、3或4；
Figure 107104578-A0305-02-0022-2
 式(II)中R4為氫或鹵素；
Figure 107104578-A0305-02-0022-3
Figure 107104578-A0305-02-0023-4
 式(III)和式(IV)中，R5、R6各自獨立地選自C1~C4的烷基；
Figure 107104578-A0305-02-0023-5
 式(V)中，R7選自用甲基、乙基或異丙氧基丙基，R8選自C1~C4的烷氧基。 A high-fastness disperse black dye composition, including component A, component B, component C and component D, wherein component A is selected from at least one compound of formula (I), component B is selected from At least one of the compounds represented by formula (II), component C is selected from at least one of compounds represented by formula (III) and/or formula (IV), and component D is selected from compounds represented by formula (V) At least one of formulas (I) to (V) has the following structure:
Figure 107104578-A0305-02-0022-1
 (I) R 1 is hydrogen or C1-C4 alkoxy, R 2 and R 3 are each independently selected from C1-C4 alkyl, m and n are independently selected from 1, 2, 3 or 4;
Figure 107104578-A0305-02-0022-2
 R 4 in formula (II) is hydrogen or halogen;
Figure 107104578-A0305-02-0022-3
Figure 107104578-A0305-02-0023-4
 In formula (III) and formula (IV), R 5 and R 6 are each independently selected from C1 to C4 alkyl groups;
Figure 107104578-A0305-02-0023-5
 In formula (V), R 7 is selected from methyl, ethyl, or isopropyloxypropyl, and R 8 is selected from C1 to C4 alkoxy. 如請求項1所述的高牢度分散黑色染料組合物，其中式(I)中R1為甲氧基或乙氧基；式(II)中R4為氯或溴；式(III)和式(IV)中，R5、R6獨立地為甲基。 The high-fastness dispersed black dye composition according to claim 1, wherein R 1 in formula (I) is methoxy or ethoxy; R 4 in formula (II) is chlorine or bromine; formula (III) and In formula (IV), R 5 and R 6 are independently methyl. 如請求項1所述的高牢度分散黑色染料組合物，其中組份D包含式(V)中R7為甲基和乙基的化合物，且甲基：乙基=1：1。 The high-fastness disperse black dye composition according to claim 1, wherein component D comprises a compound in formula (V) wherein R 7 is methyl and ethyl, and methyl:ethyl=1:1. 如請求項1所述的高牢度分散黑色染料組合物，其中組分D中包含式(V)中R7為乙基和異丙氧基丙基的化合物，且含有乙基：異丙氧基丙基=2：1。 The high-fastness dispersion black dye composition according to claim 1, wherein component D contains a compound of formula (V) wherein R 7 is ethyl and isopropoxypropyl, and contains ethyl: isopropoxy Glypropyl = 2:1. 如請求項1-4任一項所述的高牢度分散黑色染料組合物，其中組分A的重量百分含量為10~30%，組分B的重量百分含量為10~20%，組分C的重量百分含量為1~10%，組分D的重量百分含量為3~15%，餘量為助劑。 The high-fastness dispersed black dye composition according to any one of claims 1 to 4, wherein the weight percentage of component A is 10 to 30%, and the weight percentage of component B is 10 to 20%, The weight percentage of component C is 1 to 10%, the weight percentage of component D is 3 to 15%, and the balance is auxiliary. 如請求項1-4任一項所述的高牢度分散黑色染料組合物，其中所述染料組分A選自下式(I-1)~(I-9)所示染料化合物中的至少一種：
Figure 107104578-A0305-02-0024-6
Figure 107104578-A0305-02-0024-7
Figure 107104578-A0305-02-0024-8
Figure 107104578-A0305-02-0024-9
Figure 107104578-A0305-02-0025-10
Figure 107104578-A0305-02-0025-11
Figure 107104578-A0305-02-0025-12
Figure 107104578-A0305-02-0025-13
Figure 107104578-A0305-02-0025-14
 The high-fastness dispersion black dye composition according to any one of claims 1 to 4, wherein the dye component A is selected from at least at least one of the dye compounds represented by the following formulas (I-1) to (I-9) One:
Figure 107104578-A0305-02-0024-6
Figure 107104578-A0305-02-0024-7
Figure 107104578-A0305-02-0024-8
Figure 107104578-A0305-02-0024-9
Figure 107104578-A0305-02-0025-10
Figure 107104578-A0305-02-0025-11
Figure 107104578-A0305-02-0025-12
Figure 107104578-A0305-02-0025-13
Figure 107104578-A0305-02-0025-14
 如請求項1-3任一項所述的高牢度分散黑色染料組合物，其中所述染料組分B選自下式(II-1)~(II-3)所示染料化合物中的至少一種：
Figure 107104578-A0305-02-0026-16
Figure 107104578-A0305-02-0026-17
Figure 107104578-A0305-02-0026-18
 The high-fastness dispersed black dye composition according to any one of claims 1-3, wherein the dye component B is selected from at least at least one of the dye compounds represented by the following formulas (II-1) to (II-3) One:
Figure 107104578-A0305-02-0026-16
Figure 107104578-A0305-02-0026-17
Figure 107104578-A0305-02-0026-18
 如請求項1-3任一項所述的高牢度分散黑色染料組合物，其中所述染料組分C選自下式(III-1)~(III-3)、(IV-1)~(IV-3)所示染料化合物中的至少一種：
Figure 107104578-A0305-02-0026-19
Figure 107104578-A0305-02-0027-20
Figure 107104578-A0305-02-0027-21
Figure 107104578-A0305-02-0027-22
Figure 107104578-A0305-02-0027-23
Figure 107104578-A0305-02-0027-24
 The high-fastness dispersion black dye composition according to any one of claims 1-3, wherein the dye component C is selected from the following formulas (III-1) to (III-3), (IV-1) to (IV-3) At least one of the dye compounds shown:
Figure 107104578-A0305-02-0026-19
Figure 107104578-A0305-02-0027-20
Figure 107104578-A0305-02-0027-21
Figure 107104578-A0305-02-0027-22
Figure 107104578-A0305-02-0027-23
Figure 107104578-A0305-02-0027-24
 如請求項1-3任一項所述的高牢度分散黑色染料組合物，其中所述染料組分D選自下式(V-1)~(V-6)所示染料化合物中的至少一種：
Figure 107104578-A0305-02-0028-25
Figure 107104578-A0305-02-0028-26
Figure 107104578-A0305-02-0028-27
Figure 107104578-A0305-02-0028-28
Figure 107104578-A0305-02-0028-29
Figure 107104578-A0305-02-0029-30
 The high-fastness dispersed black dye composition according to any one of claims 1-3, wherein the dye component D is selected from at least at least one of the dye compounds represented by the following formulas (V-1) to (V-6) One:
Figure 107104578-A0305-02-0028-25
Figure 107104578-A0305-02-0028-26
Figure 107104578-A0305-02-0028-27
Figure 107104578-A0305-02-0028-28
Figure 107104578-A0305-02-0028-29
Figure 107104578-A0305-02-0029-30
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101982510A (en) * 2010-09-18 2011-03-02 浙江万丰化工有限公司 Composite of dispersed dyes
CN103788704A (en) * 2014-01-28 2014-05-14 杭州福莱蒽特精细化工有限公司 Disperse black dye composition for superfine fiber
CN104087015A (en) * 2013-12-25 2014-10-08 上海安诺其纺织化工股份有限公司 Navy blue or black disperse dye
CN105838109A (en) * 2016-04-29 2016-08-10 浙江龙盛集团股份有限公司 High-fastness blue to black disperse dye composition and dye product

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0519679A2 (en) * 2005-01-04 2009-03-03 Clariant Finance Bvi Ltd dispersed azorean mixtures
CN102153890B (en) * 2011-02-24 2013-06-12 绍兴县精细化工有限公司 Disperse dye composition
CN103194093B (en) 2013-03-29 2014-10-15 浙江龙盛集团股份有限公司 Composition of blue to black disperse dyes
CN106590027B (en) 2016-12-30 2020-05-01 浙江闰土研究院有限公司 Disperse dye composition and preparation method and application thereof
CN106977979B (en) * 2017-03-24 2019-03-05 江苏迪安化工有限公司 A kind of high water-washing type disperse black dye composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101982510A (en) * 2010-09-18 2011-03-02 浙江万丰化工有限公司 Composite of dispersed dyes
CN104087015A (en) * 2013-12-25 2014-10-08 上海安诺其纺织化工股份有限公司 Navy blue or black disperse dye
CN103788704A (en) * 2014-01-28 2014-05-14 杭州福莱蒽特精细化工有限公司 Disperse black dye composition for superfine fiber
CN105838109A (en) * 2016-04-29 2016-08-10 浙江龙盛集团股份有限公司 High-fastness blue to black disperse dye composition and dye product

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