CN102516811B - Disperse black dye composition - Google Patents
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- 239000000203 mixture Substances 0.000 title claims abstract description 35
- 239000000975 dye Substances 0.000 claims description 43
- 239000012752 auxiliary agent Substances 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 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 claims description 3
- 229920001732 Lignosulfonate Polymers 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 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 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000004744 fabric Substances 0.000 abstract description 9
- 238000005406 washing Methods 0.000 abstract description 5
- 238000000859 sublimation Methods 0.000 abstract description 4
- 230000008022 sublimation Effects 0.000 abstract description 4
- 238000004043 dyeing Methods 0.000 description 12
- 239000000986 disperse dye Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 238000010017 direct printing Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010016 exhaust dyeing Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 229920005552 sodium lignosulfonate Polymers 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 0 COc1cc(N=Nc(c(Br)cc([N+]([O-])=O)c2)c2[N+]([O-])=O)c(*)cc1N(*)* Chemical compound COc1cc(N=Nc(c(Br)cc([N+]([O-])=O)c2)c2[N+]([O-])=O)c(*)cc1N(*)* 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002657 fibrous material Substances 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
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000758 substrate Substances 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黑染料组合物，主要包括一种或多种结构如式(I)所示的组分A，一种或多种结构如式(II)所示的组分B，以及结构如式(III)和/或一种或多种结构如式(IV)所示的组分C；用本发明的分散染料组合物制成的染料上染疏水性纤维材料时，通过调整不同组分间的比例，可获得深浓色泽、升华牢度极佳、水洗牢度优良的黑色染织物。 The present invention provides a kind of disperse black dye composition, mainly comprise one or more components A shown in formula (I), one or more components B shown in formula (II), And structure such as formula (III) and/or one or more structures such as component C shown in formula (IV); The proportion of different components can obtain black dyed fabrics with deep color, excellent sublimation fastness and excellent washing fastness.
Description
(一)技术领域 (1) Technical field
本发明涉及一种分散黑染料组合物，尤其是一种适合印染疏水性纤维的分散黑染料组合物。The invention relates to a disperse black dye composition, in particular to a disperse black dye composition suitable for printing and dyeing hydrophobic fibers.
(二)背景技术 (2) Background technology
分散染料新品种的开发集中在20世纪90年代，进入21世纪后逐步减少，其中部分是通过商品化技术获得深色品种。染料商品化技术的研究，涉及染料与染料、染料与助剂、染料与染色基质间相互作用的超分子化学，此项技术也是当前染料商品的主要差距所在。国外许多大型染料企业基本上不生产传统纺织用染料，取而代之的是购置亚洲生产的原料，再进行复配以提高染料质量，从而获取巨额利润。The development of new varieties of disperse dyes was concentrated in the 1990s, and gradually decreased after entering the 21st century, and some of them obtained dark varieties through commercialization technology. The research on the commercialization technology of dyes involves supramolecular chemistry of the interaction between dyes and dyes, dyes and auxiliaries, and dyes and dyeing substrates. This technology is also the main gap in the current dye commercialization. Many foreign large-scale dyestuff companies basically do not produce traditional textile dyestuffs. Instead, they purchase raw materials produced in Asia and then compound them to improve the quality of dyestuffs, thereby obtaining huge profits.
分散染料需要解决的是高日晒牢度、移染性、匀染性、湿牢度、对其它纤维的沾色牢度，以及为降低热迁移现象而造成的牢度下降等，特别是提升力高的深浓色品种。分散染料复配是开发深浓色品种和超细旦纤维染色品种最有效的方法之一。What disperse dyes need to solve is high light fastness, migration, level dyeing, wet fastness, staining fastness to other fibers, and the decrease in fastness caused by reducing thermal migration. Richly colored variety of Lego. Compounding of disperse dyes is one of the most effective methods for developing deep-colored varieties and superfine-denier fiber dyed varieties.
(三)发明内容 (3) Contents of the invention
为解决上述问题，本发明提供了一种分散黑染料组合物，由其配制成的分散染料，各项坚牢度优良，特别是升华牢度突出，同时具有优异的染深性。In order to solve the above problems, the present invention provides a disperse black dye composition. The disperse dye prepared from it has excellent fastness, especially outstanding sublimation fastness, and has excellent dyeing depth.
本发明采用的技术方案是：The technical scheme adopted in the present invention is:
一种分散黑染料组合物，主要包括一种或多种结构如式(I)所示的组分A，一种或多种结构如式(II)所示的组分B，以及结构如式(III)和/或一种或多种结构如式(IV)所示的组分C，基于所述的组分A、组分B和组分C，组分A的重量百分含量为20％～85％，组分B的重量百分含量为10％～60％，组分C的重量百分含量为0.1％～20％；A disperse black dye composition, mainly comprising one or more components A with structures such as formula (I), one or more components B with structures such as formula (II), and structures such as formula (III) and/or component C with one or more structures as shown in formula (IV), based on the described component A, component B and component C, the weight percentage of component A is 20 % to 85%, the weight percentage of component B is 10% to 60%, and the weight percentage of component C is 0.1% to 20%;
式(I)中：In formula (I):
X1为卤素或-CN；X 1 is halogen or -CN;
R1、R2各自独立为C1～C4烷基；R 1 and R 2 are independently C 1 -C 4 alkyl;
R3、R4各自独立为取代的或未取代的C1～C4烷基，所述取代烷基的取代基为-OCOK1、-COOK2或-CH＝CH2，其中，K1、K2各自独立为C1～C4烷基；R 3 and R 4 are each independently substituted or unsubstituted C 1 -C 4 alkyl, and the substituent of the substituted alkyl is -OCOK 1 , -COOK 2 or -CH=CH 2 , wherein K 1 , K 2 are each independently C 1 -C 4 alkyl;
式(II)中：In formula (II):
X2为氢或卤素； X2 is hydrogen or halogen;
R5、R6各自独立为C1～C4烷基或氰乙基；R 5 and R 6 are each independently C 1 -C 4 alkyl or cyanoethyl;
式(IV)中：In formula (IV):
X3为氢、卤素或氰基； X3 is hydrogen, halogen or cyano;
R7为氢或C1～C4的烷酰氨基；R 7 is hydrogen or C 1 -C 4 alkanoylamino;
R8、R9各自独立为取代的或未取代的C1～C4烷基，所述取代烷基的取代基为氰基或-OCOK3，其中，K3为C1～C4烷基。R 8 and R 9 are each independently substituted or unsubstituted C 1 -C 4 alkyl, the substituent of the substituted alkyl is cyano or -OCOK 3 , wherein K 3 is C 1 -C 4 alkyl .
上述组分A、组分B、组分C为本发明分散黑染料组合物的主要组成，在本领域技术人员熟知的范围内，本发明组合物还可添加少量其它可应用于复配的染料单体或者助剂，通过上述改变获得的黑色染料组合物，同样在本发明的保护范围之内。The above-mentioned component A, component B, and component C are the main components of the disperse black dye composition of the present invention. Within the scope well known to those skilled in the art, the composition of the present invention can also add a small amount of other dyes that can be applied to compounding Monomers or auxiliary agents, and the black dye composition obtained through the above changes are also within the protection scope of the present invention.
优选的，基于所述的组分A、组分B和组分C，组分A的重量百分含量为40％～70％，组分B的重量百分含量为20％～50％，组分C的重量百分含量为0.1％～15％。Preferably, based on the component A, component B and component C, the weight percentage of component A is 40% to 70%, and the weight percentage of component B is 20% to 50%. The weight percent content of component C is 0.1%～15%.
优选的，所述组合物由组分A、组分B、组分C和助剂组成，基于所述组分A、组分B、组分C和助剂，所述助剂重量百分含量为35％～90％(助剂占组分A～C和助剂重量之和的百分比)。述的助剂为分散染料复配时常用的分散剂、扩散剂等，优选的，所述助剂为下列之一或其中两种以上的混合物：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Reax83A、Reax85A)等。Preferably, the composition is composed of component A, component B, component C and auxiliary agent, based on the component A, component B, component C and auxiliary agent, the weight percentage of the auxiliary agent It is 35% to 90% (the percentage of the auxiliary agent in the sum of the weight of components A to C and the auxiliary agent). Described auxiliary agent is the commonly used dispersant, diffusing agent etc. when compounding disperse dyes, preferably, described auxiliary agent is following one or the mixture of two or more thereof: naphthalenesulfonic acid formaldehyde condensate, alkylnaphthalenesulfonic acid Anionic dispersants such as formaldehyde condensate, benzylnaphthalenesulfonic acid formaldehyde condensate, lignosulfonate, etc. Specifically, naphthalenesulfonic acid formaldehyde condensate such as diffusant NNO, alkylnaphthalenesulfonic acid formaldehyde condensate such as dispersant MF (methylnaphthalenesulfonic acid formaldehyde condensate), benzylnaphthalenesulfonic acid formaldehyde condensate such as diffusing agent CNF, etc. , Lignosulfonate such as sodium lignosulfonate (such as commercially available dispersants Reax83A, Reax85A) and the like.
优选的，所述分散黑染料组合物由组分A、组分B和组分C组成，基于所述的组分A、组分B和组分C，组分A的重量百分含量为40％～70％，组分B的重量百分含量为20％～50％，组分C的重量百分含量为0.1％～15％。Preferably, the disperse black dye composition is composed of component A, component B and component C, based on the component A, component B and component C, the weight percentage of component A is 40 % to 70%, the weight percentage of component B is 20% to 50%, and the weight percentage of component C is 0.1% to 15%.
组分A优选为下列之一或其中两种以上的混合物：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以上的混合物：Component B is preferably one of the following or a mixture of two or more of them:
组分C优选为下列之一或其中两种以上的混合物：Component C is preferably one of the following or a mixture of two or more of them:
更为优选的，所述组分A为式(I-6)～(I-8)所示原染料之一或其中两种以上的混合物，所述组分B为式(II-1)所示原染料，所述组分C为式(III)和/或式(IV-1)所示原染料。More preferably, the component A is one of the original dyes represented by formulas (I-6) to (I-8) or a mixture of two or more of them, and the component B is represented by the formula (II-1). represents the primary dye, and the component C is the primary dye represented by formula (III) and/or formula (IV-1).
本发明所述的染料组合物，进行商品化过程中，通常需将原染料和助剂按前述特定的比例进行混合配制，例如将结构式(I)、(II)、(III)、(IV)所表示的原染料在助剂、水或其它润湿剂的存在下，按上述的配比混合，使用砂磨机或研磨机等粉碎机进行微粒子化后用于染色；另外也可将结构式(I)、(II)、(III)、(IV)所表示的原染料分别在助剂、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制成染料成品。In the process of commercializing the dye composition of the present invention, it is usually necessary to mix and prepare the original dye and the auxiliary agent according to the aforementioned specific ratio, for example, the structural formula (I), (II), (III), (IV) In the presence of auxiliary agents, water or other wetting agents, the original dyestuffs are mixed according to the above ratio, and then used for dyeing after micronization by using a pulverizer such as a sand mill or a grinder; in addition, the structural formula ( The primary dyes represented by I), (II), (III), and (IV) are micronized with pulverizers such as sand mills or grinders in the presence of auxiliary agents, water or other wetting agents, respectively, and then the above-mentioned The ratio is mixed to make the finished dye.
本发明所使用的式(I)～式(IV)的染料化合物可方便地按本领域技术人员熟知的方式合成，其中组分A也可以参照CN1208057中介绍的方法制备，也可采用市售商品。The dye compound of formula (I)～formula (IV) used in the present invention can be easily synthesized in a manner known to those skilled in the art, wherein component A can also be prepared with reference to the method introduced in CN1208057, and commercially available products can also be used .
利用本发明的染料组合物制成的染料，可按行业内惯用方式进行染色，如采用普通浸染法进行染色，也可用于直接印花。其中，普通浸染法如将聚酯织物进行预处理，放入染缸中进行浸染，染毕，冷水清洗至中性，绞干，再进行还原清洗，烘干；直接印花如将织物进行染前处理，烘干，定形，在印花机上印分散染料色浆，再进行蒸化，利用汽蒸方式使织物上的染料固色，最后水洗，拉幅定型。The dyestuffs made from the dyestuff composition of the present invention can be dyed in the usual manner in the industry, such as dyeing by common exhaust dyeing, and can also be used for direct printing. Among them, the ordinary exhaust dyeing method is such as pretreating the polyester fabric, putting it into the dyeing vat for dip dyeing, after dyeing, washing in cold water to neutrality, wringing, and then performing reduction cleaning and drying; direct printing is like performing pre-dyeing treatment on the fabric. , drying, setting, printing disperse dye color paste on the printing machine, and then steaming, using steaming to fix the dye on the fabric, finally washing, tentering and setting.
本发明的分散染料组合物，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成的染料上染疏水性纤维材料时，通过调整不同组分间的比例，可获得深浓色泽、升华牢度极佳、水洗牢度优良的黑色染织物。The disperse dye composition of the present invention can be supplied for dyeing in the form of micronized liquid or cream, or in the form of powder or particles dried by spray drying or the like. When the dye made of the disperse dye composition of the present invention is used to dye hydrophobic fiber materials, the black dyed fabric with deep color, excellent sublimation fastness and excellent washing fastness can be obtained by adjusting the ratio of different components.
(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61克(I-1)的组分A、35克(II-1)的组分B和4克(III)的组分C，200克分散剂MF，加水搅拌均匀，研磨分散并干燥，即得成品染料。该染料能提供给织物性能优良的深黑色。Add 61 grams of component A of (I-1), 35 grams of component B of (II-1) and 4 grams of component C of (III), 200 grams of dispersant MF, add water and stir evenly, grind and disperse and dry, That is the finished dye. The dye can provide a deep black color with excellent fabric properties.
实施例2：Example 2:
将63克(I-1)的组分A、30克(II-1)的组分B、7克(IV-1)的组分C，80克木质素磺酸钠和120克扩散剂NNO加水搅拌均匀，研磨分散并干燥，即得成品染料。该染料能提供给织物性能优良的深黑色。Component A of 63 grams of (I-1), component B of 30 grams of (II-1), component C of 7 grams of (IV-1), 80 grams of sodium lignosulfonate and 120 grams of diffusing agent NNO Add water and stir evenly, grind and disperse and dry to get the finished dye. The dye can provide a deep black color with excellent fabric properties.
实施例3～8：Embodiment 3～8:
按照表1所示数据，将组分A、组分B、组分C、组分D和助剂MF180克加水拼混后，用研磨机进行研磨分散，然后喷雾干燥，制得成品，能提供给织物性能优良的深黑色。According to the data shown in Table 1, after blending component A, component B, component C, component D and additive MF 180 grams with water, grind and disperse with a grinder, and then spray dry to obtain a finished product, which can provide Gives fabrics a deep black color with excellent properties.
表1Table 1
应用实施例：Application example:
各取2克实施例1～18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。即得一系列深浓色泽的蓝色至黑色染织物，采用ISO 105-X11、ISO 105-C03分别测试，其耐升华牢度均≥4级、耐洗涤牢度均≥4～5级。Take 2 grams of the disperse dyes prepared in Examples 1 to 18 and disperse them in 500 milliliters of water, absorb 20 milliliters and mix them with 60 milliliters of water, use acetic acid to adjust the pH of the dyeing bath to 5, 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. That is to say, a series of blue to black dyed fabrics with deep color and luster are obtained, and tested by ISO 105-X11 and ISO 105-C03 respectively, the fastness to sublimation is ≥ grade 4, and the fastness to washing is ≥ grade 4-5.
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| CN109943096A (en) * | 2019-04-13 | 2019-06-28 | 浙江欧亚数码科技有限公司 | A kind of disperse black dye composition |
| CN111484754B (en) * | 2020-04-15 | 2021-07-30 | 浙江龙盛集团股份有限公司 | A disperse blue to black dye composition and dye product |
| CN118994937A (en) * | 2024-08-09 | 2024-11-22 | 约克夏(浙江)染化有限公司 | Disperse dye composition, disperse dye, preparation method and application thereof |
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