CN110387144B - 一种分散兰染料及其用途 - Google Patents
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- 239000001045 blue dye Substances 0.000 title claims abstract description 28
- 239000000975 dye Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000012752 auxiliary agent Substances 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 238000004043 dyeing Methods 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- CBCZQJLYYRPMRI-UHFFFAOYSA-N 2-benzylnaphthalene-1-sulfonic acid Chemical compound C1=CC2=CC=CC=C2C(S(=O)(=O)O)=C1CC1=CC=CC=C1 CBCZQJLYYRPMRI-UHFFFAOYSA-N 0.000 claims description 2
- 229920001732 Lignosulfonate Polymers 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 230000002209 hydrophobic effect Effects 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 6
- 241000011547 Plebejus idas Species 0.000 abstract description 4
- 238000010438 heat treatment Methods 0.000 description 10
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 6
- 238000000227 grinding Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
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- 239000000758 substrate Substances 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910001424 calcium ion Inorganic materials 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229910001425 magnesium ion Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 230000002335 preservative effect Effects 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YMZIFDLWYUSZCC-UHFFFAOYSA-N 2,6-dibromo-4-nitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1Br YMZIFDLWYUSZCC-UHFFFAOYSA-N 0.000 description 2
- UXFWTIGUWHJKDD-UHFFFAOYSA-N 2-(4-bromobutyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCBr)C(=O)C2=C1 UXFWTIGUWHJKDD-UHFFFAOYSA-N 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- GUYMMHOQXYZMJQ-UHFFFAOYSA-N n-ethyl-3-methylaniline Chemical compound CCNC1=CC=CC(C)=C1 GUYMMHOQXYZMJQ-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
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- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
Classifications
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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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
- C09B29/0844—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 substituted by alkyl, e.g. CF3
-
- 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
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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
- C09B67/0079—Azoic dyestuff preparations
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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
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- 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
- D06P1/18—Azo dyes
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- 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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Abstract
本发明提供了一种分散兰染料及其用途,属于染料化工领域。它解决了现有分散兰XF(C.I.blue284)生产危险、污染大、染色时的耐还原性差,钙镁离子对染色的鲜艳度的影响很大等问题,一种分散兰染料,其特征在于,至少包括组分A,组分A的结构式如式(I)所示:
Description
技术领域
本发明属于染料化工领域,特别涉及一种分散兰染料及其用途。
背景技术
染料是指能使其他物质获得鲜明而牢固色泽的一类有机化合物,由于现在使用的颜料都是人工合成的,所以也称为合成染料。染料和颜料一般都是自身有颜色,并能以分子状态或分散状态使其他物质获得鲜明和牢固色泽的化合物。
分散兰XF(C.I.blue284)是一只非常鲜艳染色牢度高的重要分散染料,但是生产危险、污染大、染色时的耐还原性差,钙镁离子对染色的鲜艳度的影响很大。
分散兰XF(C.I.blue284)的化学式如下:
发明内容
本发明的第一个目的是针对现有技术中存在的上述问题,提供了一种分散兰染料;本发明的第二个目的是提供一种上述分散兰染料的应用。
本发明的第一个目的可通过下列技术方案来实现:一种分散兰染料,其特征在于,至少包括组分A,组分A的结构式如式(I)所示:
优选地,还包括组分B、组分C和组分D中的一种或几种,组分B的结构式如式(II)所示,组分C的结构式如式(III)所示,组分D的结构式如式(IV)所示:
作为优选,基于分散兰染料的总重量,它含有至少一种60-90%的组分A。
作为优选,基于分散兰染料的总重量,它含有60-90%的组分A以及5-20%的组分B或10-30%的组分C或5-25%的组分D。
优选地,还包括助剂,所述的助剂包括水和分散均染剂,所述的分散均染剂包括木质素磺酸盐、纤维素磺酸钠盐、α-萘磺酸与甲醛的缩合物、苄基萘磺酸与甲醛的缩合物中的一种或任意组合。
优选地,所述的组分A的合成包括如下步骤:
S01:偶合组分的合成:脱水剂、缚酸剂、催化剂、N-乙基间甲苯胺、N-溴丁基邻苯二甲酰亚胺,一起升温回流进行脱水反应,反应至不再出水,加水蒸出溶剂,降温结晶过滤得偶合组分;
S02:基底合成:硫酸和亚硝酰硫酸混合,控制温度在20-30℃,同时加入2,6-二溴-4-硝基苯胺,加完后,保持反应温度20-30℃,反应至终点,得到重氮盐;
偶合组分用水和硫酸溶解,降温至0℃,加入重氮盐进行偶合,终点后升温至60℃,在60℃时过滤水洗,得到基底;
S03:产物合成:二甲基乙酰胺和基底混合升温至70℃溶解,加入氰化锌、硫酸铜,升温至110℃,保持反应温度110℃,反应至终点,降温至30-40℃加入水,搅拌至结晶析出,过滤得粗品;往粗品中加入水、三氯化铁,升温至60℃,加入盐酸,盐酸加入过程中保持反应温度60℃,加完后保持60℃的温度进行反应,最后过滤水洗至中性,得到产物。
一种上述分散兰染料的应用,其特征在于,所述的分散兰染料应用于疏水性纤维或纤维的混纺物的染色。
与现有技术相比,本发明具有以下优点:
1、本发明的分散兰染料式(I)生产安全,污染小,鲜艳度好,性价高等优点,可以取代分散兰XF(C.I.blue284)。
2、本发明的分散兰染料组合物水洗牢度、耐汗牢度、升华牢度、耐水牢度均符合要求。时间温度依存性、pH依存性好,钙镁离子、均染剂和还原物质对染料的染色鲜艳度的影响小。
具体实施方式
以下是本发明的具体实施例,对本发明的技术方案作进一步的描述,但本发明并不限于这些实施例。
本发明的染料单体组分A如式(I)所示,可以通过以下方法制备得到:
组分A的合成工艺:
1、偶合组分合成
烧瓶中,加入脱水剂、缚酸剂、催化剂、N-乙基间甲苯胺、N-溴丁基邻苯二甲酰亚胺,升温回流脱水反应至不再出水,加水蒸出溶剂,降温结晶过滤得偶合组分。
2、基底合成
烧瓶中加入硫酸、亚硝酰硫酸,控制20-30℃慢慢加入2,6-二溴-4-硝基苯胺,加完保温反应至终点,得到重氮盐。
烧杯中加入水、硫酸,控制温度加入偶合组分搅拌至溶解完全,加冰降温至0℃左右,慢慢加入重氮盐进行偶合,终点后升温至60℃保温过滤水洗得基底。
3、产物合成
烧瓶中加入DMAC,基底,升温至70℃溶解,加入氰化锌、硫酸铜,升温至110℃保温反应至终点,降温至30-40℃慢慢加入水,搅拌至结晶析出,过滤得粗品。
烧杯中加入水、三氯化铁,投入上述滤饼打浆,升温至60℃,慢慢加入盐酸,加完保温反应,过滤水洗至中性,得产物。
实施例1
一种分散兰染料,由组分A、组分B和助剂组成,组分A的结构式如式(I)所示,组分B的结构式如式(II)所示,按质量分数计,组分A的质量分数为60-90%,组分B的质量分数为5-20%,其余为助剂。
该分散兰染料的制备方法为:将组分A和组分B混合后,在助剂的存在下用砂磨机或研磨机等粉碎装置进行微粒子化,即获得该分散兰染料。助剂主要为分散均染剂和水,还可含有防腐剂等。
实施例2
一种分散兰染料,由组分A、组分C和助剂组成,组分A的结构式如式(I)所示,组分C的结构式如式(III)所示,按质量分数计,组分A的质量分数为60-90%,组分C的质量分数为10-30%,其余为助剂。
该分散兰染料的制备方法为:将组分A和组分C混合后,在助剂的存在下用砂磨机或研磨机等粉碎装置进行微粒子化,即获得该分散兰染料。助剂主要为分散均染剂和水,还可含有防腐剂等。
实施例3
一种分散兰染料,由组分A、组分D和助剂组成,组分A的结构式如式(I)所示,组分D的结构式如式(IV)所示,按质量分数计,组分A的质量分数为60-90%,组分D的质量分数为5-25%,其余为助剂。
该分散兰染料的制备方法为:将组分A和组分D混合后,在助剂的存在下用砂磨机或研磨机等粉碎装置进行微粒子化,即获得该分散兰染料。助剂主要为分散均染剂和水,还可含有防腐剂等。
按照实施例1-3制备得到的分散染料,分散兰染料组合物水洗牢度、耐汗牢度、升华牢度、耐水牢度均符合要求。时间温度依存性、pH依存性好,钙镁离子、均染剂和还原物质对染料的染色鲜艳度的影响小。可以用来取代分散兰XF(C.I.blue284)。
本文中所描述的具体实施例仅仅是对本发明精神作举例说明。本发明所属技术领域的技术人员可以对所描述的具体实施例做各种各样的修改或补充或采用类似的方式替代,但并不会偏离本发明的精神或者超越所附权利要求书所定义的范围。
Claims (3)
2.根据权利要求1所述的一种分散兰染料,其特征在于,还包括助剂,所述的助剂包括水和分散均染剂,所述的分散均染剂包括木质素磺酸盐、纤维素磺酸钠盐、α-萘磺酸与甲醛的缩合物、苄基萘磺酸与甲醛的缩合物中的一种或任意组合。
3.一种如权利要求1-2任意一项所述的一种分散兰染料的应用,其特征在于,所述的分散兰染料应用于疏水性纤维或纤维的混纺物的染色。
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