CN101760045B - Medium-low temperature environmental-friendly disperse dye composition - Google Patents

Medium-low temperature environmental-friendly disperse dye composition Download PDF

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CN101760045B
CN101760045B CN 200910156642 CN200910156642A CN101760045B CN 101760045 B CN101760045 B CN 101760045B CN 200910156642 CN200910156642 CN 200910156642 CN 200910156642 A CN200910156642 A CN 200910156642A CN 101760045 B CN101760045 B CN 101760045B
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dye
dye compound
formula
compound
c1
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CN101760045A (en
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赵国生
高立江
顾伟娣
陈田木
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浙江闰土股份有限公司
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Abstract

本发明公开了一种中低温环保型分散染料组合物,按重量百分比,由以下组份组成:3%~94%如式(1)所示的染料化合物A;3%~55%如式(2)所示的染料化合物B;3%~60%如式(3)所示的染料化合物C;0~2%的如式(4)所示的染料化合物D。 The present invention discloses a low-temperature environment type disperse dye composition, in weight percent, consisting of the following components: 3% to 94% of formula (1) A dye compound represented; such as 3% to 55% of formula ( dye compound shown in FIG. 2 B); 3% to 60% as shown in equation (3) dye compound C; 0 ~ 2% of the dye compound as shown in (4) of the formula D. 本发明染料组合物色光艳丽,上染时的同步性好,重寅性好,匀染性、遮盖性及各项牢度均好,尤其是染料间的配伍性和升华牢度方面优势的更为突出,而且是环保型的,弥补了以前环保和牢度性能好不能兼得缺点。 Identifying bright light dye composition of the present invention, when a good synchronization dye, Yin weight, good leveling, hiding and are good fastness, especially fastness and sublimation compatibility between the advantages more dye to highlight, and is environmentally friendly, to make up for previous environmental protection and good fastness properties drawback can not have both.

Description

一种中低温环保型分散染料组合物 A medium type disperse dye composition cryogenic environment

技术领域 FIELD

[0001] 本发明涉及一种中低温分散染料组合物,特别适用于聚酯材料和醋纤材的染色和印花。 [0001] The present invention relates to a low temperature disperse dye composition, especially for dyeing and printing polyester and cellulose acetate material.

背景技术 Background technique

[0002] 随着近年聚酯纤维的快速发展和人们对纺织品要求的不断提高,相应的对染料本身的各项染色性能、牢度性能、环保性能也提出了更高的要求。 [0002] With the rapid development in recent years and it continues to increase polyester fiber textile requirements, the corresponding performance of the staining dye itself, fastness properties, environmental performance also put forward higher requirements.

[0003] 就黄、橙色分散染料来讲,一般的单色染料的性能较单一,要想得到较全、较好色牢度的黄色分散染料必须用多种配伍性良好、性能各有所长的单色染料进行复配。 [0003] For yellow and orange disperse dyes in terms of general performance than a single single-color pigment, in order to give a more full, good color fastness of the yellow disperse dyes must be more good compatibility, performance strengths single color dye complex. 复配染料虽然性能要比单一染料要好,但各单色染料间的配伍性决定着复合染料的染色性能和各项牢度性能。 Although the performance of complex dye is better than single dye, but compatibility among monochrome dye staining determines the properties of the composite and the dye fastness properties. 寻找配伍性良好且各项色牢度均好的黄、橙色分散染料组合物是摆在大家面前急需解决的难题之一。 Looking good compatibility and color fastness were good yellow, orange disperse dye composition is placed in front of one of the problems we need to solve.

发明内容 SUMMARY

[0004] 本发明提供一种配伍性极好,升华牢度、水洗牢度、摩擦牢度均好的环保型黄-橙色分散染料组合物。 [0004] The present invention provides an excellent compatibility, sublimation fastness, washing fastness, rubbing fastness good environmental protection yellow - orange disperse dye composition.

[0005] 本发明所述的中低温环保型分散染料组合物,按重量百分比由以下组份组成: [0005] The present invention in a low temperature environment-friendly disperse dye composition, in percentage by weight consists of the following components:

[0006] 3%〜94%如式(I)所示的染料化合物A: [0006] 3% ~94% as shown in formula (I) dye Compound A:

[0007] [0007]

Figure CN101760045BD00061

[0008] X1'X2各为卤素; [0008] X1'X2 are each halo;

[0009] 3%〜55%如式⑵所示的染料化合物B: [0009] 3% ~ 55% B shown as the dye compound of formula ⑵:

[0010] [0010]

Figure CN101760045BD00062

[0011] X3> X4、X5、X6、X7 相互独立为H 或NO2 或卤素或 [0011] X3> X4, X5, X6, X7 each independently H or NO2, or halo, or

Figure CN101760045BD00063

或OR3 或COOR4OR5OR6 Or OR3 or COOR4OR5OR6

或Ph-R7COO-或COOr8COOr9 或COOR10-Ph ;R3、R4、R5、R6、R7、R8、R9、R10 相互独立为C1 〜C4 的 Or Ph-R7COO- or COOr8COOr9 or COOR10-Ph; R3, R4, R5, R6, R7, R8, R9, R10 each independently is a C1 ~C4

烷基; alkyl;

[0012] R1 为C1 〜C4 烷基;[0013] R2为H或C1〜C4的烷基或C1〜C4的烷基中的一个氢被氧烷基取代; [0012] R1 is C1 ~C4 alkyl; [0013] R2 is H or a C1~C4 alkyl group or hydrogen C1~C4 alkyl group in the alkyl group is substituted with oxo;

[0014] 3%〜60%如式⑶所示的染料化合物C: [0014] 3% ~ 60% as the dye compound of formula C shown in ⑶:

[0015] [0015]

Figure CN101760045BD00071

[0016] x8、X9Sh 或卤素; [0016] x8, X9Sh or halogen;

[0017] Xltl为H或卤素或C1-C4的烷基; [0017] Xltl is H or halogen or a C1-C4 alkyl;

[0018] R11, R12为C1〜C4的烷基或C1〜C4的烷基中的一个氢被OH、CN或苯环取代或R13OCOR14 或 [0018] R11, R12 is a hydrogen or an alkyl group C1~C4 alkyl group in C1~C4 are OH, CN or a benzene ring or a substituted or R13OCOR14

Figure CN101760045BD00072

或R19OCOOR2。 Or R19OCOOR2. 或CH2CH = CH2 或R21OR22CN ;R13、R14, R15, R16, R17, R18, R19, R20, R21、R22 相互独立为C1 〜C4 的烷基; Or CH2CH = CH2 or R21OR22CN; R13, R14, R15, R16, R17, R18, R19, R20, R21, R22 each independently is C1 ~C4 alkyl group;

[0019] 0〜2 %的如式⑷所示的染料化合物D: [0019] 0 to 2% of the dye compound of Formula D As illustrated ⑷:

[0020] [0020]

Figure CN101760045BD00073

[0021] X11、X12相互独立为H或NO2或CN或卤素; [0021] X11, X12 each independently H or NO2 or CN or halogen;

[0022] X13为C1〜C4的烷基或NHCOR25 ;R25为C1〜C4的烷基; [0022] X13 is a C1~C4 alkyl group or NHCOR25; R25 is a C1~C4 alkyl group;

[0023] X14 为H 或OCH3 或OCH2CH3 ; [0023] X14 is H or OCH3 or OCH2CH3;

[0024] R23, R24相互独立为C1〜C4的烷基或C1〜C4烷基中的一个氢被OH、CN或苯环取代或CH2 = CHCH2 或R26OCOR27 或R28COOR29 或R3tlOCO-Ph ;R26、R27、R28、R29、R3tl 相互独立为C1 〜C4的烷基。 [0024] R23, R24 independently of one another a hydrogen or an alkyl group C1~C4 C1~C4 alkyl group is OH, CN or a benzene ring or a substituted or CH2 = CHCH2 R26OCOR27 or R28COOR29 or R3tlOCO-Ph; R26, R27, R28, R29, R3tl each independently C1 ~C4 alkyl group.

[0025] 所述的染料化合物A优选为如式(1-1)和/或式(1-2)所示的染料化合物: [0025] The dye compound A is preferably a dye of formula (1-1) and / or formula (1-2) a compound represented by:

[0026] [0026]

Figure CN101760045BD00081

[0027] 所述的染料化合物B优选为如式(2-1)〜(2-8)所示的一种染料化合物或多种染料化合物的混合物: [0027] As is shown in the formula (2-1) to (2-8) a dye compound or a mixture of the dye compound preferably more dye compound B:

[0028] [0028]

Figure CN101760045BD00082

[0029] [0029]

Figure CN101760045BD00091

[0030] 所述的染料化合物C优选为如式(3-1)〜(3-5)所示的一种染料化合物或多种染 [0030] The dye compound C is preferably a dye compound is represented by the formula (3-1) to (3-5) or more dye

料化合物的混合物: Feeding a mixture of compounds:

[0031] [0031]

Figure CN101760045BD00101

[0032] 所述的染料化合物D优选为如式(4-1)〜(4-4)所示的一种染料化合物或多种染料化合物的混合物:: [0032] As is shown in the formula (4-1) to (4-4) in a mixture of one or more dye compounds of the dye compound is preferably a dye compound D ::

[0033] [0033]

Figure CN101760045BD00102

[0034] [0034]

Figure CN101760045BD00111

[0035] 所述的染料化合物D —般加在橙色中用以调节色光,起到增深效益。 [0035] The dye compound D - like added to adjust the shade of orange, deepening functions efficiency.

[0036] 本发明所述的中低温环保型分散染料组合物,应用时一般需要加入助剂。 According to the invention in a low temperature environment-friendly disperse dye composition [0036] present, the application generally require addition of auxiliaries. 所述的助剂为分散染料复配时常用的分散剂、扩散剂及其表面活性剂等,优选包括下列之一或其混合物:萘磺酸甲醛缩合物、木质素磺酸盐、烷基萘磺酸甲醛缩合物。 The additives commonly used when complex dyes dispersants, spreading agents and surfactants and the like, or mixtures thereof, preferably comprising one of the following: naphthalenesulfonic acid-formaldehyde condensates, lignin sulfonates, alkyl naphthalene acid-formaldehyde condensates. 如甲基萘磺酸甲醛缩合物(分散剂MF)、萘磺酸甲醛缩合物(扩散剂NNO)、苄基萘磺酸甲醛缩合物(扩散剂CNF)、木质素磺酸钠(木质素85A、83A)等。 Such as methyl naphthalene sulfonate formaldehyde condensate (dispersant MF), naphthalene sulfonate formaldehyde condensate (diffusing agent NNO), benzyl-naphthalene sulfonic acid formaldehyde condensates (diffusing agent CNF), sodium lignin (lignin 85A , 83A) and so on. 通常,助剂和原染料重量之比为0.8〜5: I。 Typically, the original ratio of the weight of auxiliaries and dyes 0.8~5: I.

[0037] 本发明所述的中低温环保型分散染料组合物可用以下方法制备:将染料化合物的原染料按比例混合后,在助剂、水或其它表面活性剂存在下用砂磨机或研磨机等粉碎机进行微粒子化,然后喷雾干燥,本发明所述的中低温环保型分散染料组合物根据各染体化合物、助剂之间配比调整可得黄色到橙色色光。 [0037] environmentally friendly low-temperature disperse dye composition of the present invention can be prepared by the following method: after the original mixing of Dye compound to scale, with the presence of a sand mill or grinding aids, surfactants, water or other fine particles of a grinder, etc., and then spray dried, environmentally friendly low-temperature disperse dye composition of the present invention can be obtained as a yellow to orange color light adjusted ratio between the dye-donor compound, auxiliaries. 上述染料化合物均可采用市售产品。 The dye compound employed may be a commercially available product.

[0038] 本发明所述的分散染料组合物,微粒子化后可液状,喷雾干燥后可为粉状、颗粒状。 [0038] The disperse dye composition according to the present invention, the fine particles of the liquid can, after spray drying may be a powder, granular. 此染料组合物色光艳丽,上染时的同步性好,重寅性好,匀染性、遮盖性及各项牢度均好,尤其是染料间的配伍性和升华牢度方面优势的更为突出,而且是环保型的,弥补了以前环保和牢度性能好不能兼得缺点。 This combination of dyes looking bright light, when the dye good synchronization, re-Yin, good leveling, hiding and fastness are good, especially the sublimation fastness and compatibility between the advantages of dye more prominent, and is environmentally friendly, to make up for previous good fastness properties can not have both environmental and disadvantages.

具体实施方式 Detailed ways

`[0039] 下面结合实施例对本发明作进一步说明,但本发明的保护范围并不限于此。 `[0039] below with reference to embodiments of the present invention will be further described, although the scope of the present invention is not limited thereto.

[0040] 实施例1〜15 [0040] Example 1~15

[0041] 根据表I所示数据,将染料化合物A、染料化合物B、染料化合物C,染料化合物D,按一定比例与分散剂甲基萘磺酸甲醛缩合物(MF)、扩散剂苄基磺酸甲醛缩合物(CNF)、扩散剂萘磺酸甲醛缩合物(NNO)、木质素磺酸钠及其它表面活性剂加水拼混后,用砂磨进行研磨分散,然后进行喷雾干燥。 [0041] According to the data shown in Table I, the dye compound A, a dye compound B, compound C dyes, dye compound D, a certain proportion of the dispersant methyl naphthalene sulfonate formaldehyde condensate (MF), the diffusing agent benzylsulfonamide acid formaldehyde condensates (CNF), diffusing agent naphthalenesulfonic acid formaldehyde condensate (NNO), the lignin sulfonate and other surfactants blending with water, dispersed by a sand grinding, and then spray-dried.

[0042] 其中染料化合物(1-1)可采用浙江闰土股份有限公司生产分散黄1#,染料化合物(1-2)可采用浙江闰土股份有限公司生产分散黄2#。 [0042] wherein the dye compound (1-1) can be produced Co. of Zhejiang Disperse Yellow RunTu # 1 dye compound (1-2) can be produced soil, Inc. Zhejiang Run # 2 Yellow dispersion.

[0043] 染料化合物(2-1)可采用浙江闰土股份有限公司生产分散黄114#,染料化合物(2-2)可采用浙江闰土股份有限公司生产分散黄119#,染料化合物(2-3)可采用浙江闰土股份有限公司生产分散黄211#,染料化合物(2-4)可采用浙江闰土股份有限公司生产分散黄241#。 [0043] The dye compound (2-1) can be produced soil, Inc. Zhejiang Run # Disperse Yellow 114 dye compound (2-2) can be produced Zhejiang Run soil, Inc. Disperse Yellow # 119, the dye compound (2- 3) Run soil Zhejiang Ltd. manufactures employed Disperse yellow # 211, the dye compound (2-4) can be produced Zhejiang Run soil, Inc. Disperse yellow # 241. [0044] 染料化合物(3-1)可采用浙江闰土股份有限公司生产分散橙25#,染料化合物(3-2)可采用浙江闰土股份有限公司生产分散黄288#,染料化合物(3-3)可采用浙江闰土股份有限公司生产分散黄298#,染料化合物(3-4)可采用浙江闰土股份有限公司生产分散黄278#,染料化合物(3-5)可采用浙江闰土股份有限公司生产分散黄279#。 [0044] The dye compound (3-1) can be produced soil, Inc. Zhejiang Run # Disperse Orange 25 dye compound (3-2) can be produced Zhejiang Run soil, Inc. Disperse Yellow # 288, the dye compound (3- 3) Run soil Zhejiang Ltd. manufactures employed Disperse yellow # 298, the dye compound (3-4) can be produced soil, Inc. Zhejiang Run # Disperse yellow 278 dye compound (3-5) may be employed Run soil Zhejiang shares Co disperse yellow 279 #.

[0045] 染料化合物(4-1)可采用浙江闰土股份有限公司生产分散蓝183#,染料化合物(4-2)可采用浙江闰土股份有限公司生产分散蓝366#,染料化合物(4-3)可采用浙江闰土股份有限公司生产分散蓝291#,染料化合物(4-4)可采用浙江闰土股份有限公司生产分散蓝291:1#。 [0045] The dye compound (4-1) can be produced soil, Inc. Zhejiang Run # Disperse Blue 183 dye compound (4-2) can be produced soil, Inc. Zhejiang Run # Disperse Blue 366 dye compound (4- 3) production Co. of Zhejiang employed disperse blue # 291 RunTu dye compound (4-4) can be produced Zhejiang Run soil, Inc. of Disperse blue 291: # 1.

[0046]表 1: [0046] Table 1:

[0047] [0047]

Figure CN101760045BD00121

[0048] [0048]

Figure CN101760045BD00131

[0049] 将上述实施例制得的黄一橙色分散染料、助剂、水混合后制得的染料组合物进行性能测试,测试方法如下:[0050] 各取0.5克实施例1〜24的分散染料,用水分别配制成浓度为0.5g/500ml的分散染料悬浮液,取20ml与80ml的水混合,用醋酸调节染裕PH到5,然后升温到60°C,同时分别放入2g聚酯纤维进行高温高压染色,在35分钟内升温到130°C,保温30分钟,冷却到80°C时取样。 [0049] The above-described embodiment obtained a yellow-orange disperse dyes, adjuvants, prepared by mixing the aqueous dye composition performance test, the test method is as follows: [0050] 0.5 g pleasing Example 1~24 embodiment dispersion dyes, water were prepared at a concentration of 0.5g / 500ml of the dye suspensions, taken mixed with 80ml water 20ml, adjusted with acetic acid to PH transfected margin 5, and then warmed to 60 ° C, while polyester fibers were placed 2g high temperature high pressure dyeing was heated in 35 minutes to 130 ° C, for 30 minutes, cooling the sample to 80 ° C.

[0051]观察布样色光并采用类似 GB/T2400-1980 和GB/T3921-1997 和GB/T3920-1997 和GB/T5178-1997测定其染色牢度。 [0051] Observation colored swatches and similar GB / T2400-1980 and GB / T3921-1997 and GB / T3920-1997 and GB / T5178-1997 measured color fastness. 测定结果见表2。 The measurement results are shown in Table 2.

[0052] [0052]

Figure CN101760045BD00141
Figure CN101760045BD00151

Claims (5)

1.一种中低温环保型分散染料组合物,按重量百分比,由以下组分组成: 3%〜94%如式(1)所示的染料化合物A: An environmentally friendly low temperature disperse dye composition, in percentage by weight, comprises the following components: 3% ~94% as shown in (1) a dye of formula Compound A:
Figure CN101760045BC00021
X1^X2各为卤素; 3%〜55%如式(2)所示的染料化合物B: X1 ^ X2 are each halo; 3% ~ 55% of formula (2) shown in dye compound B:
Figure CN101760045BC00022
X3> X4> X5> X6> X7相互独立为H或NO2或卤素或d X3> X4> X5> X6> X7 each independently H or NO2, or halo, or d
Figure CN101760045BC00023
〇2或OR3 ;R3为C1〜C4的烧基; R1为C1〜C4焼基; R2为H或C1〜C4的烷基; 3%〜60%如式(3)所示的染料化合物C: 〇2 or OR3; R3 is a group C1~C4 of burning; Rl is C1~C4 ware group; R2 is H or a C1~C4 alkyl group; 3% ~ 60% as shown in equation (3) dye compound C:
Figure CN101760045BC00024
X8、X9为H或卤素; X10 为H ; Rn、R12为C1〜C4的烷基或C1〜C4的烷基中的一个氢被CN或苯环取代; 0〜2%的如式(4)所示的染料化合物D: X8, X9 is H or halo; X10 is H; Rn, R12 is a hydrogen or an alkyl group C1~C4 C1~C4 alkyl group is substituted in the phenyl ring or CN; 0 to 2% of formula (4) dye compound D shown:
Figure CN101760045BC00025
xn、X12相互独立为H或NO2或CN或卤素; X13为C1〜C4的烷基或NHCOR25 ;R25为C1〜C4的烷基; X14 为H 或OCH3 或OCH2CH3 ; R23> R24相互独立为C1〜C4的烷基或CH2=CHCH2。 xn, X12 each independently H or NO2 or CN or halogen; X13 is a C1~C4 alkyl group or NHCOR25; R25 is a C1~C4 alkyl group; X14 is H or OCH3 or OCH2CH3; R23> R24 independently of one another C1~ C4 alkyl group, or CH2 = CHCH2.
2.如权利要求1所述的中低温环保型分散染料组合物,其特征在于:所述的染料化合物A为如式(1-1)和/或式(1-2)所示的染料化合物: 2. A low-temperature environment type disperse dye composition according to claim 1, wherein: A is the dye compound of formula (1-1) and / or formula (1-2) a dye compound :
Figure CN101760045BC00031
3.如权利要求1所述的中低温环保型分散染料组合物,其特征在于:所述的染料化合物B优选为如式(2-1)〜(2-8)所示的一种染料化合物或多种染料化合物的混合物: 3. A low-temperature environment type disperse dye composition according to claim 1, wherein: said dye compound as shown in Formula B is preferably (2-1) to (2-8) a dye compound more dye compound or a mixture of:
Figure CN101760045BC00032
Figure CN101760045BC00041
4.如权利要求1所述的中低温环保型分散染料组合物,其特征在于:所述的染料化合物C优选为如式(3-1)〜(3-5)所示的一种染料化合物或多种染料化合物的混合物: 4. A cryogenic environment-friendly disperse dye composition according to claim 1, wherein: said dye compound C is preferably as shown in formula (3-1) to (3-5) a dye compound more dye compound or a mixture of:
Figure CN101760045BC00042
Figure CN101760045BC00051
5.如权利要求1所述的中低温环保型分散染料组合物,其特征在于:所述的染料化合物D优选为如式(4-1)〜(4-4)所示的一种染料化合物或多种染料化合物的混合物: 5. A cryogenic environment-friendly disperse dye composition according to claim 1, wherein: said dye is preferably a compound D as shown in Formula (4-1) to (4-4) a dye compound more dye compound or a mixture of:
Figure CN101760045BC00052
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