CN112457682B - 数码喷墨印花用分散染料墨水及其制备方法和应用 - Google Patents
数码喷墨印花用分散染料墨水及其制备方法和应用 Download PDFInfo
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- CN112457682B CN112457682B CN202011326515.2A CN202011326515A CN112457682B CN 112457682 B CN112457682 B CN 112457682B CN 202011326515 A CN202011326515 A CN 202011326515A CN 112457682 B CN112457682 B CN 112457682B
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- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical group CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 claims description 4
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical group C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 claims description 4
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- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 3
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- 235000011130 ammonium sulphate Nutrition 0.000 claims description 3
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- 229910052739 hydrogen Inorganic materials 0.000 description 7
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 7
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- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- ZLCUIOWQYBYEBG-UHFFFAOYSA-N 1-Amino-2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC=C3C(=O)C2=C1 ZLCUIOWQYBYEBG-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 2
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 2
- OSNNWHRYDJYFJL-UHFFFAOYSA-N 3-[n-(2-hydroxyethyl)-3-methylanilino]propanenitrile Chemical compound CC1=CC=CC(N(CCO)CCC#N)=C1 OSNNWHRYDJYFJL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229920004933 Terylene® Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical group C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
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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
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0085—Thiazoles or condensed thiazoles
- C09B29/0088—Benzothiazoles
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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
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- 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
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
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- 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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- 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
- C09B67/0082—Preparations of disperse dyes or solvent dyes in liquid form
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or 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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- 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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- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
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- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/30—Ink jet printing
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- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Wood Science & Technology (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
本发明公开了一种利用分散染料制备而成的数码喷墨印花用分散染料墨水,由以下质量含量的成分组成:39~41%分散染料、7.5~8.5%分散剂、19~21%多元醇、1.8~2.2%表面活性剂、0.15~0.25%消泡剂、0.15~0.25%防腐剂、0.25~0.35%pH调节剂、余量为水。本发明还公开了该数码喷墨印花用分散染料墨水的制备方法和使用方法。采用本发明方法所染涤纶织物,具有更好的耐皂洗、耐摩擦、耐升华及耐溶剂萃取等色牢度,具有广阔的应用前景。
Description
技术领域
本发明属于数码喷墨印花领域,涉及一种数码喷墨印花用分散染料墨水、其制备方法及应用方法。
背景技术
近年来数码喷墨印花技术蓬勃发展,具有工艺简单、印花精度高、无需制版、低能耗、无污水、占地面积小等优点,不断满足高品质、小批量、多品种的市场需求。
涤纶织物采用数码直喷方式进行印花时,通常会采用使用渗透剂等助剂及通过焙烘加工方式使染料进入纤维内部,同时采用还原清洗等方式除去织物表面浮色。由于染料与纤维之间主要以范德华力、氢键、疏水作用等弱作用力结合,染色印花织物在高湿热等条件下,仍有离开纤维的可能,致使染色织物色牢度下降。
吴凌霜等人筛选出三只商品分散染料,在优化的配方和工艺条件下配制成墨水,所得喷墨印花织物的K/S值高于其所选定的商品墨水,且印花织物色光鲜艳纯正,各项色牢度可达4级或4级以上(参考:吴凌霜,含氰基分散染料墨水的制备及喷墨印花性能研究[D],上海:东华大学,2016)。
筛选出的三只商品分散染料分别为分散橙BROB、分散红902和分散蓝825。其中:
分散橙BROB的结构式为:
分散红902的结构式为:
分散蓝825的结构式为:
上述墨水所使用的分散染料仍然为常规分散染料,所印花织物中染料与涤纶纤维间仍然以氢键、范德华力等弱作用力结合,在高湿热条件下,染色织物色牢度仍然会下降,而在溶剂作用下织物上染料仍然会被剥离下来。
双吖丙啶类化合物是一类新兴物质,在材料、化学、生物等领域中受到广泛研究。据报道(参考:Lepage et al.,Science 2019,366,875-878),双吖丙啶结构在高温(>100℃)或紫外光照射(波长350nm左右)条件下,会形成活泼的卡宾中间体,从而具有插入氧-氢键、氮-氢键甚至碳-氢键的能力。双吖丙啶结构通式如下:
尚未见采用以双吖丙啶染料为组成成分的分散染料墨水。
发明内容
本发明要解决的技术问题是提供一种数码喷墨印花用分散染料墨水及其制备方法和应用。
为了解决上述技术问题,本发明提供一种分散染料,被用于制备数码喷墨印花用分散染料墨水,所述分散染料为以下任一:
本发明还提供利用上述分散染料制备而成的数码喷墨印花用分散染料墨水,由以下质量含量的成分组成:
39~41%分散染料、7.5~8.5%分散剂、19~21%多元醇、1.8~2.2%表面活性剂、0.15~0.25%消泡剂、0.15~0.25%防腐剂、0.25~0.35%pH调节剂、余量为水;
所述水为去离子水。
作为本发明的数码喷墨印花用分散染料墨水的改进,其由以下质量含量的成分组成:
40%分散染料、8%分散剂、20%多元醇、2%表面活性剂、0.2%消泡剂、0.2%防腐剂、0.3%pH调节剂、余量为水。
作为本发明的数码喷墨印花用分散染料墨水的进一步改进:
所述分散剂为分散剂CNF;
所述多元醇为乙二醇:甘油=3:1质量比的混合物;
所述表面活性剂为表面活性剂XL-90;
所述消泡剂为Surfynol 104E;
所述防腐剂为1,2-苯并异噻唑啉-3-酮;
pH调节剂为三聚磷酸钠。
本发明还同时提供了上述数码喷墨印花用分散染料墨水的制备方法,包括如下步骤:
(1)将分散染料、分散剂、多元醇和去离子水在室温下采用砂磨机进行砂磨,砂磨机转速(3000±300)转/分,砂磨时间(2±0.5)h,以500nm滤膜过滤,得染料色浆;
(2)向步骤(1)所得的染料色浆加入表面活性剂、消泡剂、防腐剂、pH调节剂,搅拌均匀,得数码喷墨印花用分散染料墨水。
本发明还同时提供了上述数码喷墨印花用分散染料墨水的使用方法,包括如下步骤:
(1)将涤纶织物放入预处理液中进行浸轧预处理,二浸二轧至带液率80%,然后烘干;所述预处理液由下述质量百分数的组分组成:6%海藻酸钠,0.5%防染盐S,0.5%硫酸铵,93%水;
(2)将数码喷墨印花用分散染料墨水注入墨盒,对涤纶织物进行喷印,喷印速度0.5~3平方米/min;
(3)将喷印后的涤纶织物依次进行一次预烘、一次水洗、二次预烘、焙烘、二次水洗、烘干;所述一次预烘、二次预烘的温度均为80±5℃,所述一次预烘、二次预烘的时间均为10±1min;所述焙烘温度为160~200℃,所述焙烘时间为0.1~2h;所述烘干温度为60℃。
在发明过程中,本发明设想若分散染料墨水采用一种特殊的在一定条件下能够与涤纶纤维实现共价键结合的染料,则可在数码喷墨印花领域实现染料与织物的牢固结合,进一步提升印花织物在高湿热等极端条件下的色牢度及耐溶剂萃取等色牢度。
制备以双吖丙啶染料为组成成分的分散染料墨水并将其用于数码喷墨印花,存在以下问题:双吖丙啶染料在紫外光照射或高温下所形成的卡宾中间体十分活泼,当卡宾附近存在N-H键、O-H键和C-H键时,卡宾可能会优先与更为活泼的N-H键或O-H键反应,而难与C-H键反应;然而,墨水中通常会添加各类无机或有机助剂,这些助剂分子中含有大量的N-H键和O-H键,必然会阻碍染料与纤维的结合;另一方面,染料发色体结构中通常也会包含羟基、氨基等基团,亦会参与与卡宾的竞争反应,不利于染料与纤维间的成键反应。
因此,本发明设定了特定的数码喷墨印花用分散染料墨水和相应的使用方法,从而解决上述技术问题。
本发明与现有技术相比,具有以下技术优势:
本发明的数码喷墨印花用分散染料墨水所使用的染料具有与涤纶纤维发生化学反应的能力,可形成共价键而牢固结合;本发明使用的染料组分,结构中不含氨基氢、羟基氢等,有效降低卡宾与染料自身的副反应;本发明在常规喷印后处理工艺中多加一次预烘和一次水洗的步骤,洗去助剂,使织物上仅留有疏水性染料,从而大幅提高染料与纤维的固色率;与常规分散染料墨水相比,本发明提供的墨水所染涤纶织物具有更好的耐皂洗、耐摩擦、耐升华及耐溶剂萃取等色牢度,具有广阔的应用前景。
具体实施方式
下面通过具体实施例对本发明进行详细和具体地介绍,以使更好地理解本发明,但是下述实施例并不限制本发明范围。化合物2可由市售获得,亦可按照文献(Angew.Chem.Int.Ed.2018,57,16688-16692)提供方法合成获得;其余反应原料、试剂以及乙二醇、甘油、分散剂CNF、表面活性剂XL90、消泡剂Surfynol 104E、1,2-苯并异噻唑啉-3-酮、三聚磷酸钠均由市售获得。
浓盐酸是指质量浓度为36%~38%的盐酸。
浓硫酸是指质量浓度为98%的硫酸。
实施例1:化合物1的合成
在三口烧瓶中加入2,6-二氯苯胺20mmol(约3.24g),去离子水30ml,浓盐酸15ml,热水浴搅拌,待2,6-二氯苯胺溶解后置于冰水浴中,降温至5℃以下,加入含亚硝酸钠24mmol(约1.66g)的水溶液10ml,搅拌反应30min。加入尿素消除过量的亚硝酸,并用淀粉碘化钾试纸检测至不变蓝色为止,得到重氮盐溶液,保持冰水浴中放置,待用。
在另一三口烧瓶中加入N-氰乙基-N-羟乙基-3-甲基苯胺20mmol(约4.08g)和甲醇20ml,搅拌溶解后在冰水浴条件下滴加前述制备的全部的重氮盐溶液(滴加时间约为10~30分钟),滴加完后继续搅拌2h。静置,使所得固体析出沉淀,抽滤,水洗,干燥,在无水乙醇中重结晶,得到化合物1,黄橙色固体,5.3g,收率70.2%。
1H NMR(CDCl3,400MHz)δ7.54(d,J=6.4Hz,1H),7.43-7.42(m,3H),6.69(s,1H),6.65(d,J=7.6Hz,1H),3.81-3.79(m,4H),3.72(t,J=7.6Hz,2H),2.78(t,J=7.6Hz,2H),2.40(s,3H),1.34(s,1H).ESI-MS:m/z=375[M-H].
实施例2:染料I的合成
在氮气保护、0℃条件下,将化合物1(2mmol,0.76g)、氢化钠(60%wt in oil,2mmol,0.08g)和四氢呋喃20ml加入三口烧瓶中,搅拌反应30min;将化合物2(2mmol,0.558g)投入上述反应液中,在室温下继续搅拌反应12h;采用薄层色谱法监测反应,此时原料消耗完毕停止反应。
加水40ml、乙酸乙酯20ml,萃取三次(乙酸乙酯40ml×3),合并有机相,使用旋转蒸发仪蒸除溶剂(乙酸乙酯),残留物经200~300目的硅胶柱层析分离(洗脱剂:石油醚/乙酸乙酯=5/1,V/V)得到染料I,黄色固体,0.86g,收率74.7%。
1H NMR(CDCl3,400MHz)δ7.55(d,J=8.0Hz,1H),7.49-7.45(m,4H),7.44-7.42(m,3H),6.67-6.65(m,2H),4.47(s,2H),3.77(t,J=4.4Hz,2H),3.74-3.70(m,4H),2.78(t,J=7.6Hz,2H),2.40(s,3H).ESI-MS:m/z=575[M+H].
实施例3:化合物3的合成
在三口烧瓶中加入5,6-二氯苯并[d]噻唑-2-胺20mmol(约4.38g),浓硫酸15ml,搅拌使5,6-二氯苯并[d]噻唑-2-胺溶解,再加入去离子水30ml,置于冰水浴中,降温至5℃以下,加入含亚硝酸钠24mmol(约1.66g)的水溶液10ml,搅拌反应30min。加入尿素消除过量的亚硝酸,并用淀粉碘化钾试纸检测至不变蓝色为止,得到重氮盐溶液,保持冰水浴中放置,待用。
在另一三口烧瓶中加入N-氰乙基-N-羟乙基-3-甲基苯胺20mmol(约4.08g)和甲醇20ml,搅拌溶解后在冰水浴条件下滴加前述制备全部的重氮盐溶液,滴加完后继续搅拌2h。静置,使所得固体析出沉淀,抽滤,水洗,干燥,在无水乙醇中重结晶,得到化合物3,红色固体,6.7g,收率77.1%。1H NMR(CDCl3,400MHz)δ8.09(d,J=6.4Hz,2H),7.46(d,J=7.6Hz,1H),6.72(s,1H),6.66(d,J=7.6Hz,1H),3.81-3.79(m,4H),3.72(t,J=7.6Hz,2H),2.78(t,J=7.6Hz,2H),2.41(s,3H),1.39(s,1H).ESI-MS:m/z=432[M-H].
实施例4:染料II的合成
将化合物1替换为化合物3(2mmol,0.87g),其余等同于实施例2。得到染料II,0.82g,收率64.8%。
1H NMR(CDCl3,400MHz)δ8.09(d,J=6.8Hz,2H),7.47-7.46(m,5H),6.71-6.69(m,2H),4.47(s,2H),3.77(t,J=4.4Hz,2H),3.74-3.70(m,4H),2.78(t,J=7.6Hz,2H),2.41(s,3H).ESI-MS:m/z=633[M+H].
实施例5:化合物4的合成
将5,6-二氯苯并[d]噻唑-2-胺替换为6-硝基苯并[d]噻唑-2-胺(20mmol,3.90g),其余等同于实施例3。得到化合物4,蓝色固体,6.0g,收率73.1%。1H NMR(CDCl3,400MHz)δ8.78(s,1H),8.32(d,J=7.6Hz,1H),7.97(d,J=7.2Hz,1H),7.52(d,J=7.2Hz,1H),6.91(s,1H),6.84(d,J=7.6Hz,1H),3.81-3.79(m,4H),3.72(t,J=7.6Hz,2H),2.78(t,J=7.6Hz,2H),2.40(s,3H),1.99(s,1H).ESI-MS:m/z=409[M-H].
实施例6:染料III的合成
将化合物1替换为化合物4(2mmol,0.82g),其余等同于实施例2。得到染料III,0.95g,收率78.0%。
1H NMR(CDCl3,400MHz)δ8.79(s,1H),8.33(d,J=7.2Hz,1H),8.05(d,J=7.2Hz,1H),7.45-7.39(m,5H),6.68(d,J=7.6Hz,1H),6.64(s,1H),4.47(s,2H),3.77(t,J=4.0Hz,2H),3.76-3.70(m,4H),2.78(t,J=4.0Hz,2H),2.29(s,3H).ESI-MS:m/z=609[M+H].
实施例7:一种数码喷墨印花用分散染料墨水的制备
按质量百分份数,将40份染料I、8份分散剂CNF、15份乙二醇、5份甘油和29.3份去离子水在室温下采用砂磨机进行砂磨,砂磨机转速3000转/分,砂磨时间2h,以500nm滤膜过滤,制成染料色浆;向染料色浆中加入2份表面活性剂、0.2份消泡剂、0.2份防腐剂、0.3份pH调节剂,搅拌均匀,即成分散染料墨水成品。
表面活性剂为表面活性剂XL-90;消泡剂为Surfynol 104E;所述防腐剂为1,2-苯并异噻唑啉-3-酮;pH调节剂为三聚磷酸钠。
实施例8
将染料I替换为染料II,份数不变,其余等同于实施例7。
实施例9
将染料I替换为染料III,份数不变,其余等同于实施例7。
对比例1
将染料I替换为市售商品染料C.I.分散黄219,份数不变,其余等同于实施例7。
C.I.分散黄219的结构为:
对比例2、将染料I替换为化合物1,份数不变,其余等同于实施例7。
对比例3、将染料I替换为分散橙BROB,份数不变,其余等同于实施例7。
对比例4、将染料I替换为含有伯氨基的双吖丙啶染料A,份数不变,其余等同于实施例7。
染料A的结构为:
实验一:
按下述质量百分数的组分:6%海藻酸钠,0.5%防染盐S,0.5%硫酸铵,93%水配制预处理液,将涤纶织物放入预处理液中进行浸轧预处理,二浸二轧,带液率80%(重量%),烘干备用(60℃烘干60分钟);将实施例7所制备的墨水注入墨盒,在数码直喷印花机上对涤纶织物进行喷印色条,喷印速度1平方米/min;
后处理工艺:将喷印后涤纶织物在80℃下一次预烘10min,取出用清水进行一次冲洗(至洗涤液为中性),再在80℃下二次预烘10min,随后在180℃下焙烘0.5h,取出用清水进行二次冲洗(至洗涤液为中性),最后在60℃下烘干(60℃烘干60分钟),得到黄色喷印涤纶织物。采用Data Color测色配色仪测试染色织物表面色深值(K/S)。
实验二:将实验一中喷印涤纶织物放入装有N,N-二甲基甲酰胺(100ml)的单口烧瓶中,加热至120℃,保持30min,取出织物冷却,用清水冲洗,晾干,测试织物K/S值。
实施例7~9均按实验一和实验二提供方法进行实验,结果见表1:
表1
由表1的实施例7~9的结果可以看出,染料I~染料III所染涤纶织物具有较好的得色量,经N,N-二甲基甲酰胺萃取后仍然有大部分染料留于纤维上;对比例1~3结果表明,采用不含双吖丙啶结构的染料所制得的墨水打印的织物上染料与涤纶纤维间无共价键,纤维上染料能够被N,N-二甲基甲酰胺全部萃取下来;上述结果间接证明了本发明提供的染料能够与涤纶纤维有效发生共价键结合;对比例4结果表明,当染料分子中含有伯氨基时,最终打印织物上的染料有大量被萃取下来,其原因可能是所形成的卡宾与染料自身发生了反应而未能与纤维结合致使效果明显下降。
实验三:按照标准GB/T 3921-2008、GB/T 3920-2008和GB/T 6152-1997测试实验一中各染色织物的耐皂洗色牢度、耐摩擦色牢度和耐升华色牢度。结果见表2。
表2
由表2结果可知,本发明提供的反应性分散染料染色织物具有很好的耐皂洗、耐摩擦及耐升华色牢度。
实施例7-1:将实验一中焙烘温度改为160℃,其余等同于实施例7。
实施例7-2:将实验一中焙烘温度改为200℃,其余等同于实施例7。
实施例7-3:将实验一中焙烘时间改为0.2h,其余等同于实施例7。
实施例7-4:将实验一中焙烘时间改为1.0h,其余等同于实施例7。
实施例7-5:将实验一中焙烘时间改为2.0h,其余等同于实施例7。
将上述实施例7-1~实施例7-2按照实验一和实验二所述方法进行检测,所得结果如下表3所述。
表3
表4
由表3及表4结果可知,在本发明提供的条件之下,染色涤纶织物均能具有很好的得色量、耐溶剂萃取能力及优异的各项色牢度结果。
对比例5:将实施例9所得墨水按照实验一进行的后处理工艺改成:
将喷印后涤纶织物在80℃下预烘10min,随后在180℃下焙烘0.5h,取出用清水冲洗,最后在60℃下烘干,其余等同于实验一。
所得的黄色喷印涤纶织物,采用Data Color测色配色仪测试染色织物表面色深值(K/S)。并进行实验二剥色实验。
对比例6:将实施例9所得墨水按照实验一进行的后处理工艺改成:
将喷印后涤纶织物在80℃下预烘10min,取出用清水冲洗,随后在180℃下焙烘0.5h,取出用清水冲洗,最后在60℃下烘干,其余等同于实验一。
所得的黄色喷印涤纶织物,采用Data Color测色配色仪测试染色织物表面色深值(K/S)。并进行实验二剥色实验。
对比例7:将实施例9所得墨水按照实验一进行的后处理工艺改成:
将喷印后涤纶织物用清水冲洗,在80℃下预烘10min,随后在180℃下焙烘0.5h,取出用清水冲洗,最后在60℃下烘干,其余等同于实验一。
所得的黄色喷印涤纶织物,采用Data Color测色配色仪测试染色织物表面色深值(K/S)。并进行实验二剥色实验。
对比例8:将实施例9所得墨水按照实验一进行的后处理工艺改成:
将喷印后涤纶织物在180℃下焙烘0.5h,取出用清水冲洗,最后在60℃下烘干,其余等同于实验一。
所得的黄色喷印涤纶织物,采用Data Color测色配色仪测试染色织物表面色深值(K/S)。并进行实验二剥色实验。
所得结果如下表5所述。
表5
对比例5~8结果表明,本发明提供的墨水需要配合特定的印花方法才能取得更好的得色量及固色率等打印效果。
最后,还需要注意的是,以上列举的仅是本发明的若干个具体实施例。显然,本发明不限于以上实施例,还可以有许多变形。本领域的普通技术人员能从本发明公开的内容直接导出或联想到的所有变形,均应认为是本发明的保护范围。
Claims (6)
2.利用如权利要求1所述的分散染料制备而成的数码喷墨印花用分散染料墨水,其特征在于由以下质量含量的成分组成:
39~41%分散染料、7.5~8.5%分散剂、19~21%多元醇、1.8~2.2%表面活性剂、0.15~0.25%消泡剂、0.15~0.25%防腐剂、0.25~0.35%pH调节剂、余量为水;
所述水为去离子水。
3.根据权利要求2所述的数码喷墨印花用分散染料墨水,其特征在于由以下质量含量的成分组成:
40%分散染料、8%分散剂、20%多元醇、2%表面活性剂、0.2%消泡剂、0.2%防腐剂、0.3%pH调节剂、余量为水。
4.根据权利要求3所述的数码喷墨印花用分散染料墨水,其特征在于:
所述分散剂为分散剂CNF;
所述多元醇为乙二醇:甘油=3:1质量比的混合物;
所述表面活性剂为表面活性剂XL-90;
所述消泡剂为Surfynol 104E;
所述防腐剂为1,2-苯并异噻唑啉-3-酮;
pH调节剂为三聚磷酸钠。
5.如权利要求2~4任一所述的数码喷墨印花用分散染料墨水的制备方法,其特征在于包括如下步骤:
(1)将分散染料、分散剂、多元醇和去离子水在室温下采用砂磨机进行砂磨,砂磨机转速3000±300转/分,砂磨时间2±0.5 h,以500 nm滤膜过滤,得染料色浆;
(2)向步骤(1)所得的染料色浆加入表面活性剂、消泡剂、防腐剂、pH调节剂,搅拌均匀,得数码喷墨印花用分散染料墨水。
6.如权利要求2~4任一所述的数码喷墨印花用分散染料墨水的使用方法,其特征在于包括如下步骤:
(1)将涤纶织物放入预处理液中进行浸轧预处理,二浸二轧至带液率80%,然后烘干;所述预处理液由下述质量百分数的组分组成:6%海藻酸钠,0.5%防染盐S,0.5%硫酸铵,93%水;
(2)将数码喷墨印花用分散染料墨水注入墨盒,对涤纶织物进行喷印,喷印速度0.5~3平方米/min;
将喷印后的涤纶织物依次进行一次预烘、一次水洗、二次预烘、焙烘、二次水洗、烘干;所述一次预烘、二次预烘的温度均为80±5℃,所述一次预烘、二次预烘的时间均为10±1min;所述焙烘温度为160~200℃,所述焙烘时间为0.1~2 h;所述烘干温度为60℃。
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