CN114144480A - 纤维活性染料、其制备及其用途 - Google Patents
纤维活性染料、其制备及其用途 Download PDFInfo
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- CN114144480A CN114144480A CN202080055063.0A CN202080055063A CN114144480A CN 114144480 A CN114144480 A CN 114144480A CN 202080055063 A CN202080055063 A CN 202080055063A CN 114144480 A CN114144480 A CN 114144480A
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- dye
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- dyes
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- 239000000985 reactive dye Substances 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title description 4
- 238000004043 dyeing Methods 0.000 claims abstract description 24
- 238000007639 printing Methods 0.000 claims abstract description 21
- 239000000835 fiber Substances 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 15
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 7
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 6
- 229910004727 OSO3H Inorganic materials 0.000 claims abstract description 5
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 239000000975 dye Substances 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- -1 and R2is H Chemical group 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
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- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
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- 238000004519 manufacturing process Methods 0.000 claims description 2
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- 239000004744 fabric Substances 0.000 description 12
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- 210000002268 wool Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 229910052744 lithium Inorganic materials 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
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- 229910052700 potassium Inorganic materials 0.000 description 3
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- 235000013772 propylene glycol Nutrition 0.000 description 3
- 239000004328 sodium tetraborate Substances 0.000 description 3
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- AVGVFDSUDIUXEU-UHFFFAOYSA-N 2-octyl-1,2-thiazolidin-3-one Chemical compound CCCCCCCCN1SCCC1=O AVGVFDSUDIUXEU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 239000002202 Polyethylene glycol Substances 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
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- 150000001879 copper Chemical class 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
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- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
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- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
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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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
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- C09B62/515—Metal complex azo dyes
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- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/20—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a pyrimidine ring
- C09B62/24—Azo dyes
- C09B62/255—Metal complex azo dyes
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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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/004—Mixtures of two or more reactive dyes
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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
- C09B67/0033—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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Abstract
Description
本发明涉及具有两个纤维反应性基团的蓝色染色铜配合物活性染料,涉及含有所述铜配合物染料的混合物,涉及其制备方法及其在纺织品纤维材料的染色或印花中的用途。
可用于含羟基或含氮的纤维材料,如棉或毛的染色和印花的纤维活性铜配合物染料是已知的并描述在例如US 4885360、US 527886、GB 2239024和DE 3707549中。
现今需要具有足够的直染性并同时具有未固定染料的良好易洗除性的活性染料。它们还应具有良好的着色率和高反应性,目的尤其是提供具有高固色度的染色品(dyeings)和印花品(prints)。染料还应产生具有良好的全面牢度性质,例如耐光牢度和耐湿牢度性质的染色品和印花品。迄今已知的纤维活性金属配合物染料不能满足所有这些要求。特别地,用已知染料制备的染色品具有不足的耐洗牢度和耐氯漂牢度。
因此,本发明基于的问题是,对于纤维材料的染色或印花,找出非常具有上面表征的品质的新型改进的蓝色染色纤维活性染料。
本发明因此涉及下式的活性染料
其中
M是氢、碱金属或1当量的碱土金属,
Z1是乙烯基、β-硫酸根合乙基(β-sulfatoethyl)或基团-NHCO-(CH2)3-SO2-CH2CH2Cl,
R1是指H或磺基,且
R2是H、甲基、甲氧基或磺基,
n是数值3,
Y是乙烯基或基团-CH2-CH2-U且U是-Cl或-OSO3H。
式(1)的染料含有至少3,优选3至5,尤其是4或5个磺基。磺基-SO3M以游离酸形式(M是氢)或优选以盐形式存在。合适的盐是例如碱金属或碱土金属盐。考虑的其它盐是铵盐、有机胺的盐或其混合物。可提到的实例是钠、锂、钾或铵盐、单-、二-或三-乙醇胺盐或混合Na/Li或Na/Li/NH4盐。
Z1优选是β-硫酸根合乙基或-NHCO-(CH2)3-SO2-CH2CH2Cl。
本发明的一个优选实施方案涉及式(1)的活性染料,其中R1是指H。
在某一实施方案中,Y是基团-CH2-CH2-U且U是-Cl或-OSO3H,U优选是Cl。
特别优选的是下式的染料
其中
M如上文定义,
Z1是β-硫酸根合乙基或-NHCO-(CH2)3-SO2-CH2CH2Cl,
R1是指H或磺基,且
R2是H、甲基、甲氧基或磺基。
根据本发明的染料表现出与其它活性染料的高相容性并因此可与其它染料组合应用以调节特定色调或用在双色或三色混合物中。
因此,本发明进一步涉及一种染料混合物,其包含
(A) 20至60重量%,优选25至55重量%,特别是30至50重量%的一种或多种式(1)的活性染料,和
(B) 40至80重量%,优选45至75重量%,特别是50至70重量%的至少一种不同于式(1)的染料的蓝色、黄色、橙色或棕色染色活性染料,
各百分比基于所有染料的总和计。
适合作为根据本发明的混合物中的组分(B)的染料的实例是C.I. R BL 19、C.I.R BL 49、C.I. R BL 100、C.I. R BL101、C.I. R BL144、C.I. R BL 145、C.I. R BL 146、C.I. R BL 147、C.I. R BL 194、C.I. R BL 198、C.I. R BL 220、C.I. R BL 221、C.I. RBL 222、C.I. R BL 223、C.I. R BL 225、C.I. R BL 235、C.I. R BL 244、C.I. R BL 260、C.I. R BL 261、C.I. R BL 262、C.I. R BL 268、C.I. R BL 269、C.I. R BL 275、C.I. RBL 279、C.I. R BL 282、C.I. R BL 284、C.I. R YE 95、C.I. R YE 143、C.I. R YE 168、C.I. R YE 174、C.I. R YE 175、C.I. R YE 205、C.I. R YE 206、C.I. R YE 207、C.I. RYE 208、C.I. R YE 209、C.I. R YE 210、C.I. R YE 214、C.I. R YE 217、C.I. R YE 218、C.I. R YE 219、C.I. R YE 222、C.I. R OR 13、C.I. R OR 35、C.I. R OR 116、C.I. R OR131、C.I. R OR 132、C.I. R OR 133、C.I. R OR 134、C.I. R OR 135、C.I. R OR 137、C.I. R OR 140和C.I. R OR 143。
优选地,根据本发明的染料混合物包含选自C.I. R BL 220、C.I. R BL 235、C.I.R BL 19和C.I. R BL 279的一种或多种染料作为组分(B)。
本发明进一步涉及一种制备式(1)的活性染料的方法,其包括
(a) 将下式的化合物重氮化
其中R1、R2和Z1具有如上文定义的含义且R6是指H或C1-C6烷基;
和使由此获得的重氮盐与下式的偶联组分反应
其中M如上文定义;
由此获得下式的偶氮化合物
其中R1、R2、Z1、R6、M和p如上文定义;
(b) 使式(6)的化合物与式(7)的化合物反应
其中M如上文定义,
Cl-CO-(CH2)n-SO2Y (7),
其中Y和n如上文定义,
由此提供下式的化合物
其中M、Y和n如上文定义;
(c) 将步骤(a)中制备的式(5)的化合物重氮化并使由此获得的重氮盐与步骤(b)中制备的式(8)的偶联组分反应;和
(d) 使步骤(c)中制备的双偶氮染料与Cu(II)盐在水溶液中在pH < 7下反应,由此提供式(1)的铜配合物染料。
式(3)、(4)、(6)和(7)的反应物(educts)是已知的或可根据已知方法制备。
合适的式(3)的化合物是例如2-羟基-4-β-硫酸根合乙基-1-氨基苯、2-羟基-5-甲氧基-4-β-硫酸根合乙基-1-氨基苯、2-羟基-5-甲基-4-β-硫酸根合乙基-1-氨基苯、2-甲氧基-4-β-硫酸根合乙基-1-氨基苯、2-羟基-4-[4-(β-氯乙基)丁酰氨基]-1-氨基苯和2-甲氧基-4-[4-(β-氯乙基)丁酰氨基]-1-氨基苯。
在步骤(a)中,通常将式(3)的胺在低温下在无机酸水溶液中通过亚硝酸的作用重氮化,并在弱酸性、中性或弱碱性pH下进行与式(4)的偶联组分的反应。
式(7)的酰基氯的具体实例是:Cl-CO-(CH2)3-SO2-(CH2)2-Cl和Cl-CO-(CH2)3-SO2-CH=CH2。
式(7)的化合物是本身已知的或可类似于如例如GB-A-1155149中描述的已知化合物制备。
在步骤(b)中,式(6)的胺化合物优选在水溶液、乳液或悬浮液中在低温,例如0℃至40℃下,和在弱酸性、中性或弱碱性pH下用式(7)的化合物转化。有利地,通过加入碱金属氢氧化物、碳酸盐或碳酸氢盐的水溶液连续中和在缩合反应过程中释放的卤化氢。
在步骤(c)中,通常将式(5)的中间体在低温下在无机酸水溶液中通过亚硝酸的作用重氮化,并在弱酸性、中性或弱碱性pH下进行与式(8)的偶联组分的反应。
在步骤(d)中,最后,使步骤(c)中制备的双偶氮染料与Cu(II)盐在水溶液中反应。
合适的Cu(II)盐是例如铜的简单盐和配合盐,例如硫酸铜、氯化铜、乙酸铜或碳酸铜,和水杨酸或酒石酸的铜盐。
如果使用无机酸的铜盐,方便地在酸缓冲剂,例如碱金属氢氧化物或碳酸盐、或碱土金属氢氧化物或碳酸盐、或低级烷烃羧酸,如乙酸的碱金属盐,或磷酸的碱性碱金属盐存在下进行反应。这些碱金属化合物或碱土金属化合物特别是钠、钾和钙化合物,优选例如氢氧化钠、氢氧化钾、氢氧化钙、碳酸钠和碳酸钾、碳酸钙、碳酸氢钠、乙酸钠、磷酸氢二钠和磷酸三钠。
Cu(II)盐以大约等摩尔量使用,以将一个铜原子引入要形成的式(1)的化合物的每一个分子。该金属化通常在室温下已达到完全。
由于上文提到的各个方法步骤可以不同顺序进行,以及在一些情况下如果适当,同时进行,可能有不同的方法变体。该反应通常逐步相继进行,各个反应组分之间的本身已知的简单反应的顺序取决于特定条件。
根据本发明的式(1)的活性染料以游离酸形式或优选以其盐形式存在。考虑的盐是例如碱金属、碱土金属和铵盐,或有机胺的盐。作为实例可提到钠、锂、钾和铵盐,和单-、二-和三-乙醇胺的盐。
根据本发明的纤维活性染料适用于多种多样的材料,尤其是含羟基或含氮的纤维材料的染色和印花,特别适用于印花。实例包括纸、丝、皮革、毛、聚酰胺纤维和聚氨酯,尤其是所有类型的纤维素纤维材料。这样的纤维材料是例如天然纤维素纤维,如棉、亚麻和大麻,以及纤维素和再生纤维素。根据本发明的染料也适用于存在于混纺织物,例如棉和聚酯纤维或聚酰胺纤维的混纺物中的含羟基纤维的染色或印花。
本发明因此还涉及根据本发明的活性染料在含羟基或含氮,尤其是含棉的纤维材料的染色或印花中的用途,或换言之,涉及含羟基或含氮的纤维材料的染色或印花方法,其中使用式(1)的活性染料。
根据本发明的活性染料可以各种方式,尤其是以染料水溶液或染料印花浆的形式施加到纤维材料上并固定到纤维上。它们既适用于浸染工艺又适用于根据轧染工艺的染色;它们可在低染色温度下使用,并且在轧蒸工艺中只需要短的汽蒸时间。固色度高,且未固定的染料可容易地洗掉,上染率与固色度之间的差异非常小,也就是说皂洗损失(soaping loss)非常小。根据本发明的活性染料也适用于印花,尤其是在棉上印花,以及适用于含氮纤维,例如毛或丝或含毛的混纺织物的印花。
使用根据本发明的活性染料制成的染色品和印花品在酸性和碱性范围内都具有高着色强度和高纤维-染料结合稳定性,还具有良好的耐光牢度和极好的耐湿牢度性质,如耐洗牢度、耐水牢度、耐海水牢度、耐交染牢度和耐汗牢度。特别地,所得的染色品和印花品表现出与已知染料相比改进的耐氯漂牢度和耐洗牢度性质。
根据本发明的式(1)的染料也适合作为用于记录系统的着色剂。这样的记录系统是例如用于纸或纺织品印刷的市售喷墨印刷机,或书写工具,如钢笔或圆珠笔,尤其是喷墨印刷机。为此,首先将根据本发明的染料制成适用于记录系统的形式。合适的形式是例如包含根据本发明的染料作为着色剂的水性墨水。墨水可以常规方式通过在所需量的水中将各组分混合在一起而制备。
作为基底,考虑上文提到的含羟基或含氮的纤维材料,尤其是棉纤维材料。纤维材料优选是纺织品纤维材料。
还可考虑的基底是纸和塑料膜。
作为纸的实例,可提到市售的喷墨纸、照相纸、光面纸、塑料涂布纸,例如EpsonInk-jet Paper、Epson Photo Paper、Epson Glossy Paper、Epson Glossy Film、HPSpecial Ink-jet Paper、Encad Photo Gloss Paper和IIford Photo Paper。塑料膜是例如透明或浑浊/不透明的。合适的塑料膜是例如3M Transparency Film。
根据应用的性质,例如纺织品印刷或纸印刷,可能必须例如相应地调节墨水的粘度或其它物理性质,尤其是影响对所涉基底的亲合力的性质。
用于水性墨水的染料应该优选具有低盐含量,也就是说它们应该具有基于染料重量计小于0.5重量%的总盐含量。由于染料的制备和/或由于稀释剂的后续添加而具有相对高盐含量的染料可例如通过膜分离程序,如超滤、反渗透或渗析脱盐。
墨水优选具有基于墨水的总重量计1至35重量%,尤其是1至30重量%,优选1至20重量%的染料总含量。优选的下限在这种情况下是1.5重量%,优选2重量%,尤其是3重量%的界限。
墨水可包含水混溶性有机溶剂,例如C1-C4醇,例如甲醇、乙醇、正丙醇、异丙醇、正丁醇、仲丁醇、叔丁醇或异丁醇;酰胺,例如二甲基甲酰胺或二甲基乙酰胺;酮或酮醇,例如丙酮或二丙酮醇;醚,例如四氢呋喃或二氧杂环己烷;含氮杂环化合物,例如N-甲基-2-吡咯烷酮或1,3-二甲基-2-咪唑烷酮,聚亚烷基二醇,例如聚乙二醇或聚丙二醇;C2-C6亚烷基二醇和硫二醇,例如乙二醇、丙二醇、丁二醇、三乙二醇、硫二甘醇、己二醇和二乙二醇;其它多元醇,例如甘油或1,2,6-己三醇;和多元醇的C1-C4烷基醚,例如2-甲氧基乙醇、2-(2-甲氧基乙氧基)乙醇、2-(2-乙氧基乙氧基)乙醇、2-[2-(2-甲氧基乙氧基)乙氧基]乙醇或2-[2-(2-乙氧基乙氧基)乙氧基]乙醇;优选N-甲基-2-吡咯烷酮、二乙二醇、甘油或尤其是1,2-丙二醇,其量通常为基于墨水总重量计2至30重量%,尤其是5至30重量%,优选10至25重量%。
此外,墨水还可包含增溶剂,例如ε-己内酰胺。
墨水可包含天然或合成来源的增稠剂,尤其用于调节粘度。
可提到的增稠剂的实例包括市售藻酸盐增稠剂、淀粉醚或刺槐豆粉醚,尤其是藻酸钠,其单独或与改性纤维素,例如甲基纤维素、乙基纤维素、羧甲基纤维素、羟乙基纤维素、甲基羟乙基纤维素、羟丙基纤维素或羟丙基甲基纤维素,尤其与优选20至25重量%羧甲基纤维素混合。也可提到的合成增稠剂是例如基于聚(甲基)丙烯酸或聚(甲基)丙烯酰胺以及具有例如2000至20 000的分子量的聚亚烷基二醇,例如聚乙二醇或聚丙二醇或环氧乙烷与环氧丙烷的混合聚亚烷基二醇的那些。
墨水含有例如基于墨水总重量计0.01至2重量%,尤其是0.01至1重量%,优选0.01至0.5重量%的量的此类增稠剂。
墨水还可包含缓冲物质,例如硼砂、硼酸盐、磷酸盐、聚磷酸盐或柠檬酸盐。可提到的实例包括硼砂、硼酸钠、四硼酸钠、磷酸二氢钠、磷酸氢二钠、三聚磷酸钠、五聚磷酸钠和柠檬酸钠。它们尤其以基于墨水总重量计0.1至3重量%,优选0.1至1重量%的量使用,以建立例如4至9,尤其是5至8.5的pH值。
作为进一步添加剂,墨水可包含表面活性剂或湿润剂。
合适的表面活性剂包括市售阴离子型或非离子型表面活性剂。作为根据本发明的墨水中的湿润剂,可考虑例如脲,或乳酸钠(有利地为50%至60%水溶液的形式)和甘油和/或丙二醇的混合物,其量优选为0.1至30重量%,尤其是2至30重量%。
优选的是具有1至40 mPa·s,尤其是1至20 mPa·s,更尤其是1至10 mPa·s的粘度的墨水。
此外,墨水可另外包含常规添加剂,例如消泡剂或尤其是抑制真菌和/或细菌生长的防腐剂。这样的添加剂通常以基于墨水总重量计0.01至1重量%的量使用。
作为防腐剂,考虑的是甲醛生成剂,例如低聚甲醛和三氧杂环己烷,尤其是大约30至40重量%甲醛的水溶液,咪唑化合物,例如2-(4-噻唑基)苯并咪唑,噻唑化合物,例如1,2-苯并异噻唑啉-3-酮或2-正辛基-异噻唑啉-3-酮,碘化合物、腈、酚、卤烷基硫代化合物或吡啶衍生物,尤其是1,2-苯并异噻唑啉-3-酮或2-正辛基-异噻唑啉-3-酮。合适的防腐剂是例如1,2-苯并异噻唑啉-3-酮在二丙二醇中的20重量%溶液(Proxel® GXL)。
墨水可另外包含其它添加剂,如氟化聚合物或调聚物,例如基于墨水总重量计例如0.01至1重量%的量的聚乙氧基全氟醇(Forafac®或Zonyl®产品)。
在喷墨印刷法的情况下,将独立墨滴以受控方式从喷嘴喷射到基底上。为此目的主要使用连续喷墨法和按需喷墨法。在连续喷墨法的情况下,连续产生液滴,将印刷操作不需要的液滴排放到容器中并回收。另一方面,在按需喷墨法的情况下,按需产生液滴并用于印刷;也就是说,仅在印刷操作需要时才产生液滴。液滴的产生可以例如借助压电喷墨头或通过热能(气泡喷射)实现。优选借助压电喷墨头印刷和根据连续喷墨法印刷。
本发明因此还涉及包含根据本发明的式(1)的染料的水性墨水和这样的墨水在用于印刷各种基底,尤其是纺织品纤维材料的喷墨印刷法中的用途,上文指出的定义和优选项适用于染料、墨水和基底。
本发明的染料表现出非常好的提升(build-up)行为、高端提升率(high endbuild-up)和高固色度,尤其是在纤维素纤维材料上的印刷应用中。
以下实施例用于举例说明本发明。除非另行指明,温度以摄氏度给出,份数是重量份且百分比涉及重量百分比。重量份以千克/升的比率与体积份相关联。
实施例1:
(a) 将细分散在200份水中的62.2份2-甲氧基-4-(β-硫酸根合乙基磺酰基)-1-氨基苯在pH < 1.5和20℃下通过加入17.5份亚硝酸钠而重氮化。将反应混合物搅拌1小时并通过加入氨基磺酸破坏过量亚硝酸盐。
(b) 将63.9份2-氨基-1,7-二磺基-5-羟基萘细分散在700份水中并使用30%氢氧化钠溶液将pH设定为6.0。通过加冰,使温度保持在5-20℃。然后在5-20℃经30分钟加入(i)中获得的重氮盐,同时使用30%氢氧化钠溶液使pH保持在6.0。
(c) 将63.9份1-氨基-3,6-二磺基-8-萘酚细分散在400份水和100份冰中。通过使用30%氢氧化钠溶液,将pH设定为7.0。在加入300份冰后,通过使用20%苏打溶液将pH保持在7.0-7.5和将温度保持在0-10℃,将62.5份β-氯乙基磺酰基丁酰氯缓慢添加到上述溶液中。
(d) 将150份水、150份冰和60份盐酸(32%)混合在一起。在pH < 1.5和0-15℃的温度下向其中缓慢加入根据(b)获得的化合物和17.5份亚硝酸钠的混合物。将所得混合物搅拌30分钟。通过加入氨基磺酸破坏过量亚硝酸盐。
(e) 将根据(d)获得的混合物在pH 6.5和0-20℃的温度下经1小时添加到用150份冰预先冷却的根据(c)获得的混合物中。通过使用30%氢氧化钠溶液使pH保持在6.5的值。在添加完成后,将该混合物搅拌另外1小时。
(f) 将根据(e)获得的混合物与32.2份氯化铜(II)合并,并使用20%苏打溶液将pH设定至4.5的值。然后将所得混合物在95-100℃下在通过使用20%苏打溶液保持的pH 4.5下搅拌30小时。在反应完成后,将pH调节到6.0并通过本领域中公知的方法分离所得染料,例如通过使用渗析膜脱盐。获得305份粗制染料(λmax: 576 nm),其主要组分(为游离酸形式)对应于下式
实施例2-4: 可以类似于实施例1中所述的方式制备以下染料,其各自以良好的全面牢度性质将纤维素染成蓝色至紫色色调。
应用实施例1
轧堆染色:
在具有75%(70%)染液吸液率(liquor pick-up)的挤压效果(squeezing effect)的轧染机上,用每升含有X克根据实施例4获得的式(104)的染料、1克润湿剂(ALBAFLOW®PAD)、20毫升氢氧化钠36°Bé和70毫升硅酸钠(水玻璃)38°Bé的水性染液浸渍漂白(丝光处理)的印花棉织物(cotton cretonne fabric)。浸渍时间为2秒。在轧染后,将织物卷起,然后在25℃的温度下储存24小时。在储存后,将染色的棉材料用水冷冲洗(10分钟),在水中煮沸(5分钟),随后用水冷冲洗(10分钟)。用染液1至3根据染料浓度(X g/l)获得不同颜色深度的蓝色调织物。
用光谱测定法(photospectrometrically)测量染色品的着色强度。表1概括提升性质。根据实施例4制备的染料表现出极好的提升性质。
表1: 提升率: 参考深度(RD)与染料浓度的相关性
染浴 | 1 | 2 | 3 |
实施例3的染料[ X g/l] | 10 | 20 | 60 |
漂白的印花棉织物 | 0.76 | 1.27 | 2.28 |
丝光处理的印花棉织物 | 1.12 | 1.88 | 3.11 |
应用实施例2
如应用实施例1中所述,用包含30.0重量份式(103)的染料和70.0重量份式(901)的染料的混合物将印花棉织物染色
根据染料浓度(X g/l),用含有不同量的染料混合物的染液获得不同颜色深度的蓝色调织物。
用光谱测定法测量染色品的着色强度。表2概括提升性质。式(103)的染料和式(901)的染料的混合物表现出极好的提升性质。
表2: 提升率: 参考深度(RD)与染料浓度的相关性
染料混合物的浓度[%] | 0.50 | 1.00 | 2.00 | 4.00 | 6.00 | 8.00 |
颜色深度 | 0.35 | 0.64 | 1.19 | 2.14 | 2.64 | 3.15 |
对根据上述方法用30重量%的式(103)的染料和70重量%的式(901)的染料的混合物染色的漂白印花棉织物施以氙气耐光牢度测试(ISO 105/E03)。根据灰色标度测定颜色变化。该织物评级为4。
Claims (11)
2.根据权利要求1的式(1)的活性染料,其中Z1是β-硫酸根合乙基或-NHCO-(CH2)3-SO2-CH2CH2Cl。
3.根据权利要求1或2的式(1)的活性染料,其中R1是指H。
4.根据权利要求1至3任一项的式(1)的活性染料,其中Y是基团-CH2-CH2-U且U是-Cl或-OSO3H,U优选是Cl。
6.一种染料混合物,其包含
(A) 20-60重量%的一种或多种根据权利要求1的式(1)的活性染料,和
(B) 40-80重量%的至少一种不同于式(1)的染料的蓝色、黄色、橙色或棕色染色活性染料,
各百分比基于所有染料的总和计。
7.根据权利要求10的染料混合物,其包含选自C.I. R BL 220、C.I. R BL 235、C.I. RBL 19和C.I. R BL 279的一种或多种染料作为组分(B)。
8.一种制备式(1)的活性染料的方法,其包括
(a) 将下式的化合物重氮化
其中R1、R2和Z1具有如权利要求1中定义的含义,且R6是指H或C1-C6烷基;
和使由此获得的重氮盐与下式的偶联组分反应
其中M如权利要求1中定义;
由此获得下式的偶氮化合物
其中R1、R2、Z1、R6、M和p如上文定义;
(b) 使式(6)的化合物与式(7)的化合物反应
其中M如权利要求1中定义,
Cl-CO-(CH2)n-SO2Y (7),
其中Y和n如权利要求1中定义,
由此提供下式的化合物
其中M、Y和n如权利要求1中定义;
(c) 将步骤(a)中制备的式(5)的化合物重氮化并使由此获得的重氮盐与步骤(b)中制备的式(8)的偶联组分反应;和
(d) 使步骤(c)中制备的双偶氮染料与Cu(II)盐在水溶液中在pH < 7下反应,由此提供根据权利要求1的式(1)的铜配合物染料。
9.根据权利要求1至5任一项的活性染料或根据权利要求6或7的活性染料的混合物在含羟基或含氮的纤维材料的染色或印花中的用途。
10.含羟基或含氮的纤维材料的染色或印花方法,其中使用根据权利要求1至5任一项的活性染料或根据权利要求6或7的活性染料的混合物。
11.一种水性墨水,其包含至少一种式(1)的染料。
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CN101735653A (zh) * | 2009-11-16 | 2010-06-16 | 天津德凯化工股份有限公司 | 毛用红色活性染料及其制备方法 |
CN102660145A (zh) * | 2012-04-28 | 2012-09-12 | 浙江万丰化工有限公司 | 用于分散/活性同浆印花的分散染料组合物及制备和应用 |
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US527886A (en) | 1894-10-23 | Coin-controlled machine | ||
DE1644155B2 (de) | 1965-09-07 | 1977-04-07 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von disazofarbstoffen und deren metallkomplexverbindungen |
NL6714218A (zh) | 1966-11-03 | 1968-05-06 | ||
EP0114032B1 (de) | 1982-12-20 | 1987-07-01 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
DE3707549A1 (de) | 1987-03-10 | 1988-09-22 | Bayer Ag | Reaktivfarbstoffe |
GB2239024B (en) | 1989-12-16 | 1993-04-21 | Sandoz Ltd | Fibre-reactive dyestuffs |
US5330539A (en) | 1991-12-18 | 1994-07-19 | Hoechst Celanese Corporation | Fiber reactive dyes - applications with low salt |
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2020
- 2020-06-24 WO PCT/EP2020/067678 patent/WO2021018485A1/en unknown
- 2020-06-24 US US17/629,810 patent/US12006437B2/en active Active
- 2020-06-24 CN CN202080055063.0A patent/CN114144480A/zh active Pending
- 2020-06-24 EP EP20734201.5A patent/EP4004122A1/en active Pending
- 2020-06-24 BR BR112022000593A patent/BR112022000593A8/pt unknown
- 2020-06-24 KR KR1020227006981A patent/KR20220044308A/ko unknown
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US3457251A (en) * | 1965-08-28 | 1969-07-22 | Hoechst Ag | Metal complexes of diazo dyestuffs |
GB1305271A (zh) * | 1969-02-20 | 1973-01-31 | ||
US4649193A (en) * | 1980-05-24 | 1987-03-10 | Hoechst Aktiengesellschaft | Water-soluble dyestuffs containing fibre-reactive groups of the vinylsulfone series and the fluoro-s-triazinyl-amino series |
CN1659240A (zh) * | 2002-06-11 | 2005-08-24 | 德意志戴斯达纺织品及染料两合公司 | 水溶性纤维活性双偶氮染料、其制备方法和用途 |
CN101735653A (zh) * | 2009-11-16 | 2010-06-16 | 天津德凯化工股份有限公司 | 毛用红色活性染料及其制备方法 |
CN102660145A (zh) * | 2012-04-28 | 2012-09-12 | 浙江万丰化工有限公司 | 用于分散/活性同浆印花的分散染料组合物及制备和应用 |
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US12006437B2 (en) | 2024-06-11 |
BR112022000593A2 (pt) | 2022-03-03 |
US20220259435A1 (en) | 2022-08-18 |
WO2021018485A1 (en) | 2021-02-04 |
KR20220044308A (ko) | 2022-04-07 |
BR112022000593A8 (pt) | 2023-05-09 |
EP4004122A1 (en) | 2022-06-01 |
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Effective date of registration: 20230208 Address after: Basel, SUI Applicant after: Huntsman Textile Dyeing (Switzerland) Co.,Ltd. Address before: Basel, SUI Applicant before: HUNTSMAN ADVANCED MATERIALS (SWITZERLAND) GmbH |