CN100577743C - A kind of disperse yellow dye composition - Google Patents
A kind of disperse yellow dye composition Download PDFInfo
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- CN100577743C CN100577743C CN 200710069793 CN200710069793A CN100577743C CN 100577743 C CN100577743 C CN 100577743C CN 200710069793 CN200710069793 CN 200710069793 CN 200710069793 A CN200710069793 A CN 200710069793A CN 100577743 C CN100577743 C CN 100577743C
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- 239000000203 mixture Substances 0.000 title claims abstract description 24
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000001043 yellow dye Substances 0.000 title claims abstract description 15
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000000975 dye Substances 0.000 abstract description 23
- 239000004744 fabric Substances 0.000 abstract description 9
- 239000000986 disperse dye Substances 0.000 abstract description 8
- 229920000728 polyester Polymers 0.000 abstract description 4
- 239000002657 fibrous material Substances 0.000 abstract description 2
- 210000004243 sweat Anatomy 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000012752 auxiliary agent Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 229920005552 sodium lignosulfonate Polymers 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 1
- NMDKWAQVRNUKQH-UHFFFAOYSA-N 2-benzylnaphthalene-1-sulfonic acid formaldehyde Chemical compound C=O.C(C1=CC=CC=C1)C1=C(C2=CC=CC=C2C=C1)S(=O)(=O)O NMDKWAQVRNUKQH-UHFFFAOYSA-N 0.000 description 1
- RTZYVAQWQXPIAC-UHFFFAOYSA-N 4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound C1=CC(O)=CC=C1N=NC1=CC=C(N=NC=2C=CC=CC=2)C=C1 RTZYVAQWQXPIAC-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WQHQCQSAAOGHQP-UHFFFAOYSA-N formaldehyde;2-methylnaphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WQHQCQSAAOGHQP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- BMUXKUVOASOJKR-UHFFFAOYSA-N methyl 3-[4-[(2-chloro-4-nitrophenyl)diazenyl]-n-(2-cyanoethyl)anilino]propanoate Chemical compound C1=CC(N(CCC#N)CCC(=O)OC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl BMUXKUVOASOJKR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
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Abstract
本发明提供了一种分散黄染料组合物,主要包括一种或多种结构如式(I)所示的组分A和一种或多种结构如式(II)所示的组分B,基于所述的组分A和组分B,所述组分A重量分数为5~40%,所述组分B重量分数为60~95%;用本发明的分散染料组合物制得的染料染聚酯纤维材料时,通过调整不同组分间的比例,可获得具有色光艳丽、分散性好、耐洗、耐汗渍等优良性能的黄色染织物。
The invention provides a disperse yellow dye composition, which mainly comprises one or more components A having a structure as shown in formula (I) and one or more components B having a structure as shown in formula (II). Based on the components A and B, the weight fraction of the component A is 5-40%, and the weight fraction of the component B is 60-95%. When the dye prepared by the disperse dye composition of the invention is used to dye polyester fiber materials, a yellow dyed fabric having excellent properties such as bright color, good dispersibility, washability, and sweat resistance can be obtained by adjusting the ratio between different components.
Description
(一)技术领域 (1) Technical field
本发明涉及一种分散黄染料组合物,尤其涉及一种涤纶及其混纺织物印染用的分散黄染料组合物。The invention relates to a disperse yellow dye composition, in particular to a disperse yellow dye composition for printing and dyeing polyester and its blended fabrics.
(二)背景技术 (2) Background technology
随着近年聚酯新纤维的快速发展和人们对纺织品要求的提高,相应地,对染料本身具有的染色性能、环保性能也提出了更高的要求。既要求染料有高的提升力和各项染色坚牢度,又要求染料具有良好的环保性能,以避免对环境造成污染。With the rapid development of new polyester fibers in recent years and the improvement of people's requirements for textiles, correspondingly, higher requirements have been put forward for the dyeing performance and environmental protection performance of the dye itself. Not only the dyestuffs are required to have high lifting power and various dyeing fastnesses, but also the dyestuffs are required to have good environmental performance to avoid pollution to the environment.
就分散染料而言,大规模开发新型染料结构的工作已不多见,而大量的工作转向了染料的应用性能、染料之间以及染料与助剂的复配增效的研究上。如分散黄RGFL因其色泽鲜艳,扩散速度快,遮盖性、匀染性良好,耐日晒、耐洗涤、耐酸碱、耐汗渍性能良好,且能与分散红3B和分散蓝2BLN组成性能良好的低温型三原色而得以广泛应用。但由于分散黄RGFL(C.I.分散黄23)被德国政府Oeko-Tex Standard 100和欧盟Eco-Label列入禁用分散染料中,因此世界各国都大力对其代用品进行研究和开发,专利CN1125240中公开的染料染色性能良好,但上染织物色光不够鲜亮。As far as disperse dyes are concerned, the large-scale development of new dye structures is rare, and a lot of work has turned to the research on the application performance of dyes, the synergy between dyes and the compounding and synergy of dyes and auxiliaries. For example, disperse yellow RGFL has bright color, fast diffusion speed, good covering and level dyeing properties, good resistance to sunlight, washing, acid and alkali, and perspiration, and can be combined with disperse red 3B and disperse blue 2BLN. The low-temperature three primary colors can be widely used. However, since Disperse Yellow RGFL (C.I. Disperse Yellow 23) is listed in the banned disperse dyes by the German government Oeko-Tex Standard 100 and the EU Eco-Label, all countries in the world are vigorously researching and developing its substitutes, disclosed in the patent CN1125240 The dyeing performance of the dye is good, but the shade of the dyed fabric is not bright enough.
(三)发明内容 (3) Contents of the invention
本发明目的既是为了提供一种染料组合物,以获得一种性能优异、色光艳丽的环保型分散黄染料。The object of the present invention is to provide a dye composition to obtain an environment-friendly disperse yellow dye with excellent performance and bright shade.
为达到发明目的本发明采用的技术方案是:For achieving the purpose of the invention, the technical scheme adopted by the present invention is:
一种分散黄染料组合物,主要包括一种或多种结构如式(I)所示的组分A和一种或多种结构如式(II)所示的组分B,基于所述的组分A和组分B,所述组分A重量分数为5~40%,所述组分B重量分数为60~95%;A disperse yellow dye composition, mainly comprising one or more components A as shown in formula (I) and one or more components B as shown in formula (II), based on the Component A and component B, the weight fraction of the component A is 5-40%, and the weight fraction of the component B is 60-95%;
式(I)中,R1为-H、-Cl、-Br或-CN,R2为C1~C4的烷基、氰乙基、-C2H4COOCH3或苯乙基;In formula (I), R 1 is -H, -Cl, -Br or -CN, R 2 is C 1 ~ C 4 alkyl, cyanoethyl, -C 2 H 4 COOCH 3 or phenethyl;
式(II)中,R3为C1~C4的烷基;R4为卤素、-CO-Ph、-SO2Ph、-COOC2H5或-SO2NH2,R5为-H、或-NO2。In formula (II), R 3 is C 1 ~ C 4 alkyl; R 4 is halogen, -CO-Ph, -SO 2 Ph, -COOC 2 H 5 or -SO 2 NH 2 , R 5 is -H , or -NO 2 .
优选的,基于所述的组分A和组分B,组分A重量分数为20~40%,组分B重量分数为60~80%。Preferably, based on the component A and component B, the weight fraction of component A is 20-40%, and the weight fraction of component B is 60-80%.
更为优选的,所述分散黄染料组合物由组分A和组分B组成,组分A重量分数为20~40%,组分B重量分数为60~80%。More preferably, the disperse yellow dye composition is composed of component A and component B, the weight fraction of component A is 20-40%, and the weight fraction of component B is 60-80%.
所述分散黄染料组合物中还可含有一种或多种结构如式(III)所示的组分C;基于所述的组分A、组分B和组分C,组分A的重量分数为8~35%,组分B的重量分数为60~90%,组分C的重量分数为2~30%;Also can contain one or more structures such as component C shown in formula (III) in the described disperse yellow dye composition; Based on described component A, component B and component C, the weight of component A The fraction is 8-35%, the weight fraction of component B is 60-90%, and the weight fraction of component C is 2-30%;
优选的,基于所述的组分A、组分B和组分C,组分A的重量分数为10~30%,组分B的重量分数为60~80%,组分C的重量分数为5~20%。Preferably, based on the component A, component B and component C, the weight fraction of component A is 10-30%, the weight fraction of component B is 60-80%, and the weight fraction of component C is 5-20%.
更为优选的,所述分散黄染料组合物由组分A、组分B和组分C组成,组分A的重量分数为10~30%,组分B的重量分数为60~80%,组分C的重量分数为5~20%。More preferably, the disperse yellow dye composition is composed of component A, component B and component C, the weight fraction of component A is 10-30%, and the weight fraction of component B is 60-80%, The weight fraction of component C is 5-20%.
组分A优选为下列之一或其中两种或两种以上的混合物:Component A is preferably one of the following or a mixture of two or more of them:
组分B优选为下列之一或其中两种或两种以上的混合物:Component B is preferably one of the following or a mixture of two or more of them:
由于染料行业的特殊性,很难也没有必要制成纯品,通常会带有一些制备过程中的杂质,本发明的分散染料组合物制成成品染料时也允许含有少量的水份及微量的物理杂质。Due to the particularity of the dye industry, it is difficult and unnecessary to make a pure product, which usually contains some impurities in the preparation process. When the disperse dye composition of the present invention is made into a finished dye, it is also allowed to contain a small amount of water and a small amount of physical impurities.
配制本发明的分散染料组合,所使用的式(I)、式(II)及式(III)的染料单体化合物可方便地按本领域技术人员熟知的方式合成,也可以参照专利US4194882和GB1313092中介绍的方法或类似的方法制备,也可采用市售产品。To prepare the disperse dye combination of the present invention, the dye monomer compounds of the formula (I), formula (II) and formula (III) used can be easily synthesized in a manner well known to those skilled in the art, and can also refer to patent US4194882 and GB1313092 Prepared by the method described in or a similar method, commercially available products can also be used.
本发明的分散黄染料组合物,应用于染色时需经商品化处理,如一般需要加入助剂进行分散。例如将组分A、组分B和组分C所表示的染料单体按上述的配比混合后,在助剂、水或其它润湿剂的存在下用砂磨机或研磨机等粉碎机进行微粒子化;另外也可将组分A、组分B和组分C所表示的染料单体分别在助剂、水或其它润湿剂的存在下用砂磨机或研磨机等粉碎机进行微粒子化处理后以上述的比例进行混合。通常,助剂与原染料重量之比为0.8~5∶1。The disperse yellow dye composition of the present invention needs to be commercialized when it is applied to dyeing, and generally needs to be dispersed by adding an auxiliary agent. For example, after mixing the dye monomers represented by component A, component B and component C according to the above ratio, in the presence of additives, water or other wetting agents, use a pulverizer such as a sand mill or a grinder to Carry out micronization; In addition, the dye monomers represented by component A, component B and component C can also be processed with a pulverizer such as a sand mill or a grinder in the presence of auxiliary agents, water or other wetting agents. After the micronization treatment, it is mixed at the ratio mentioned above. Usually, the weight ratio of the auxiliary agent to the original dyestuff is 0.8-5:1.
所述的助剂为分散染料复配时常用的分散剂、扩散剂等,优选下列之一或其任意几种的混合物:萘磺酸甲醛缩合物、烷基萘磺酸甲醛缩合物、苄基萘磺酸甲醛缩合物、木质素磺酸盐等阴离子分散剂。具体地,萘磺酸甲醛缩合物如扩散剂NNO,烷基萘磺酸甲醛缩合物如分散剂MF(甲基萘磺酸甲醛缩合物),苄基萘磺酸甲醛缩合物如扩散剂CNF等,木质素磺酸盐如木质素磺酸钠(如市售分散剂Reax 83A、Reax 85A)等。The auxiliary agent is a dispersant, a diffusing agent, etc. commonly used in the compounding of disperse dyes, preferably one of the following or a mixture of any of them: naphthalenesulfonic acid formaldehyde condensate, alkylnaphthalenesulfonic acid formaldehyde condensate, benzyl Anionic dispersants such as naphthalenesulfonic acid formaldehyde condensate and lignosulfonate. Specifically, naphthalenesulfonic acid formaldehyde condensate such as diffusant NNO, alkylnaphthalenesulfonic acid formaldehyde condensate such as dispersant MF (methylnaphthalenesulfonic acid formaldehyde condensate), benzyl naphthalenesulfonic acid formaldehyde condensate such as diffusing agent CNF, etc. , lignosulfonate such as sodium lignosulfonate (such as commercially available dispersants Reax 83A, Reax 85A), etc.
本发明的分散黄染料组合物,经商品化处理后,可以微粒子化后的液态、乳膏态或者用喷雾干燥法等进行干燥后的粉状、颗粒状态供给染色。用本发明的分散染料组合物制得的染料染聚酯纤维材料时,通过调整不同组分间的比例,可获得具有色光艳丽、分散性好、耐洗、耐汗渍等优良性能的黄色染织物。The disperse yellow dye composition of the present invention, after being commercialized, can be supplied for dyeing in a liquid state, a cream state after micronization, or in a powder state or a particle state after drying by a spray drying method or the like. When dyeing polyester fiber materials with the dyes prepared from the disperse dye composition of the present invention, by adjusting the ratio of different components, yellow dyed fabrics with excellent properties such as bright shade, good dispersibility, washability and perspiration resistance can be obtained .
(四)具体实施方式(4) Specific implementation methods
下面结合具体实施例对本发明进行进一步描述,但本发明的保护范围并不仅限于此:The present invention is further described below in conjunction with specific embodiment, but protection scope of the present invention is not limited thereto:
实施例1:Example 1:
将34克式(I-1)的组分A、66克式(II-1)的组分B、160克的木质素磺酸钠,加水600克拼混后,用研磨机研磨分散,喷雾干燥,即得成品,该染料能提供给织物均匀而牢度性能良好的亮丽黄色。Component A of 34 grams of formula (I-1), component B of 66 grams of formula (II-1), sodium lignosulfonate of 160 grams, after adding 600 grams of water and blending, grind and disperse with a grinder, spray After drying, the finished product is obtained. The dye can provide uniform bright yellow color to the fabric with good fastness properties.
实施例2:Example 2:
将22克式(I-1)的组分A、64克式(II-1)的组分B、14克式(III)的组分C、180克的木质素磺酸钠,加水600克拼混后,用研磨机研磨分散,喷雾干燥,即得成品,该染料能提供给织物均匀而牢度性能良好的亮丽黄色。Component A of 22 grams of formula (I-1), component B of 64 grams of formula (II-1), component C of 14 grams of formula (III), sodium lignosulfonate of 180 grams, add water 600 grams After blending, use a grinder to grind and disperse, and spray dry to obtain the finished product. The dye can provide uniform bright yellow color to the fabric with good fastness.
实施例3~13:Embodiment 3~13:
按照表1所示数据,将组分A、组分B、组分C、195克助剂(市购)、加水600克拼混后,用研磨机进行研磨分散,然后喷雾干燥,制得成品。According to the data shown in Table 1, after component A, component B, component C, 195 grams of additives (commercially available), and 600 grams of water are added to blend, grind and disperse with a grinder, and then spray dry to obtain a finished product .
表1Table 1
实施例14:Example 14:
各取0.5克实施例1~13制得的分散染料分散在500毫升水中,吸取20毫升后与60毫升的水混合,用醋酸调染浴PH为5,升温至70℃同时放入2克聚酯纤维进行染色,于30分钟内由70℃升温到130℃,保温30分钟,冷却至90℃时开始取样。观察样布色光,采用国标GB/T3921-1997、GB/T3920-1997及GB/T3922-1997,分别测试其耐洗、耐摩擦、耐汗渍色牢度,结果表明:样布色光艳丽、各项色牢度均达4~5级。Take 0.5 grams of the disperse dyes prepared in Examples 1 to 13 and disperse them in 500 milliliters of water, absorb 20 milliliters and mix them with 60 milliliters of water, adjust the pH of the dyeing bath to 5 with acetic acid, heat up to 70°C and put 2 grams of poly The ester fiber is dyed, the temperature is raised from 70°C to 130°C within 30 minutes, the temperature is kept for 30 minutes, and the sampling starts when it is cooled to 90°C. Observe the color and light of the sample cloth, and use the national standard GB/T3921-1997, GB/T3920-1997 and GB/T3922-1997 to test its color fastness to washing, rubbing and perspiration respectively. The color fastness is up to grade 4-5.
实施例15(对比例):Embodiment 15 (comparative example):
将75克式(II-1)的染料和25克C.I.分散红54【式(IV)】的染料、160克的木质素磺酸钠,加水600克拼混后,用研磨机研磨分散,喷雾干燥,即得成品分散黄染料。With the dyestuff of 75 grams of formula (II-1) and 25 grams of C.I. Disperse Red 54 [formula (IV)] dyestuff, 160 grams of sodium lignosulfonate, after adding 600 grams of water, blend, grind and disperse with grinder, spray After drying, the finished disperse yellow dye is obtained.
实施例16:Example 16:
将实施例1、实施例2及实施例15中制得的染料按照实施例14中的步骤进行染色,并根据残液法在722型分光光度计上测定各自的上染率。结果表明:实施例1、2中的染料上染步骤基本一致,而实施例15中的染料在初染时速率较快,70~100℃染色阶段出现了色花,且样布色光不及实施例1、2中上染的样布色光鲜艳。The dyes prepared in Example 1, Example 2 and Example 15 were dyed according to the steps in Example 14, and the respective dye uptake was measured on a 722-type spectrophotometer according to the raffinate method. The results show that the dyeing steps in Examples 1 and 2 are basically the same, but the dye in Example 15 has a faster dyeing rate at the initial dyeing stage, and color flowers appear in the dyeing stage at 70-100°C, and the color light of the sample cloth is not as good as that of Example 1. The color of the sample cloth dyed in 1 and 2 is bright.
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CN 200710069793 Expired - Fee Related CN100577743C (en) | 2007-06-29 | 2007-06-29 | A kind of disperse yellow dye composition |
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CN101880476B (en) * | 2010-06-29 | 2013-09-11 | 浙江龙盛染料化工有限公司 | Yellow-to-orange disperse dye composition |
CN101935465B (en) * | 2010-08-26 | 2013-11-20 | 浙江龙盛集团股份有限公司 | Disperse yellow brown dye composition |
KR20140127336A (en) | 2012-02-29 | 2014-11-03 | 캐논 가부시끼가이샤 | Pigment dispersion and yellow resist composition for color filter and ink composition containing the pigment dispersion |
CN103059603B (en) * | 2013-01-10 | 2015-03-11 | 浙江山峪染料化工有限公司 | Disperse yellow dye prescription |
CN103059604A (en) * | 2013-01-10 | 2013-04-24 | 浙江山峪染料化工有限公司 | Disperse yellow dye |
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CN104530757B (en) * | 2014-12-31 | 2017-02-22 | 浙江闰土股份有限公司 | Yellow disperse dye combination, disperse dye and preparation method and application of disperse dye |
CN104788996B (en) * | 2015-04-29 | 2017-03-08 | 杭州福莱蒽特精细化工有限公司 | A kind of yellowish-brown dye composition |
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CN108841202B (en) * | 2018-05-29 | 2020-01-03 | 绍兴金绿洲新材料科技有限公司 | Disperse yellow dye mixture with improved sublimation fastness |
CN110776757B (en) * | 2019-12-13 | 2021-09-17 | 浙江闰土股份有限公司 | Golden yellow disperse dye composition, golden yellow disperse dye and preparation method and application thereof |
CN111662569B (en) * | 2020-07-10 | 2021-09-17 | 约克夏(浙江)染化有限公司 | Orange disperse dye composition, orange disperse dye, and preparation method and application thereof |
CN112574594B (en) * | 2020-12-31 | 2023-05-23 | 绍兴市上虞金冠化工有限公司 | Disperse yellow-orange dye composition and product thereof |
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