TWI461408B - 酸染料 - Google Patents
酸染料 Download PDFInfo
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- TWI461408B TWI461408B TW098122064A TW98122064A TWI461408B TW I461408 B TWI461408 B TW I461408B TW 098122064 A TW098122064 A TW 098122064A TW 98122064 A TW98122064 A TW 98122064A TW I461408 B TWI461408 B TW I461408B
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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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/021—Disazo dyes characterised by two coupling components of the same type
- C09B35/03—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a heterocyclic compound
- C09B35/031—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a heterocyclic compound containing a six membered ring with one nitrogen atom as the only ring hetero atom
-
- 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
- D06P1/39—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 acid dyes
-
- 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
-
- 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/205—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl- or triaryl- alkane or-alkene
- C09B35/21—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl- or triaryl- alkane or-alkene of diarylmethane or triarylmethane
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/26—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl urea
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/28—Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O—
- C09B35/30—Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O— from two identical coupling components
-
- 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
-
- 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
-
- 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
- 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
- D06P3/001—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated using acid dyes
-
- 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
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/021—Material containing basic nitrogen using acid dyes
-
- 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
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/06—Material containing basic nitrogen containing amide groups using acid dyes
-
- 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
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
-
- 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
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
- D06P3/16—Wool using acid 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
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid 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
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/32—Material containing basic nitrogen containing amide groups leather skins
- D06P3/3206—Material containing basic nitrogen containing amide groups leather skins using acid dyes
- D06P3/3226—Material containing basic nitrogen containing amide groups leather skins using acid dyes dis-polyazo
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- 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
- 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
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/6008—Natural or regenerated cellulose using acid dyes
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- 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
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- D06P5/30—Ink jet printing
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- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/28—Colorants ; Pigments or opacifying agents
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H13/00—Pulp or paper, comprising synthetic cellulose or non-cellulose fibres or web-forming material
- D21H13/10—Organic non-cellulose fibres
- D21H13/20—Organic non-cellulose fibres from macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H13/26—Polyamides; Polyimides
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- Wood Science & Technology (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pyridine Compounds (AREA)
- Ink Jet (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Description
本發明係關於一種新穎的酸染料、其製備方法及其用於為有機基材染色之用途。
眾所周知酸染料且亦了解具有連橋部分的染料。然而,仍需要具有改良性質的酸染料。
本發明提供一種通式(I)化合物,
其中R0
表示經取代的C1
至C4
烷基或未經取代的C1
至C4
烷基,R1
表示H、經取代的C1
至C4
烷基或未經取代的C1
至C4
烷基、磺酸基、-CO-NH-(C1
至C4
烷基)或CN,R2
表示H、或未經取代的C1
至C4
烷基,R3
表示H、磺酸基、經取代的C1
至C4
烷基或未經取代的C1
至C4
烷基、經取代的C1
至C4
烷氧基或未經取代的C1
至C4
烷氧基,R4
表示H、經取代的C1
至C4
烷基或未經取代的C1
至C4
烷基、經取代的C1
至C4
烷氧基或未經取代的C1
至C4
烷氧基,B 為具有分子式-NH-CO-NH-、-CR5
R6
-的基團,其中R5
表示H、經取代之C1
至C9
烷基或未經取代之C1
至C9
烷基,R6
表示H、經取代之C1
至C9
烷基或未經取代之C1
至C9
烷基、未經取代之芳基或經取代的芳基或R5
與R6
一起形成五或六員環脂族環,其中該五或六員環係由C1
至C4
烷基取代或該五或六員環未經進一步取代。
R5
與R6
的碳原子總數較佳為至少4個碳原子,R5
與R6
更佳總共具有至少5個碳原子。R5
與R6
的碳原子總數甚至更佳為5或6或7或8或9個碳原子。
較佳的結構式(I)化合物具有至少一個陰離子取代基,較佳為1或2或3個陰離子取代基,其中以2個陰離子取代基特別佳。
在結構式(I)化合物中,至少一個陰離子取代基較佳置於取代基R1
及/或R3
其中一處,至少一個陰離子取代基更佳置於其中一個取代基R2
處。較佳置於其中一個取代基處亦指該取代基為陰離子基團。
較佳的陰離子取代基為羧基及/或磺酸基,且磺酸基最佳。
取代基C1
至C4
烷基中較佳取代基係選自以下取代基:-OH、-O(C1
至C4
-烷基)、-SO3
H、-COOH、-NH(C1
至C4
-烷基)。取代基C1
至C4
烷基之更佳取代基係選自以下取代基:-OH、-O(C1
至C4
-烷基)、-SO3
H、-COOH、-NH(C1
至C4
-烷基)。烷基為直鏈或分支鏈。最佳烷基為甲基、乙基、丙基、異丙基、丁基、異丁基(2-甲基丙基)、戊基、異戊基(3-甲基丁基)、己基、庚基、辛基或壬基。
取代基C1
至C4
烷氧基之較佳取代基係選自以下取代基:-OH、-O(C1
至C4
-烷基)、-SO3
H、-COOH、-NH(C1
至C4
-烷基)。烷氧基為直鏈或分支鏈。
經取代的芳基之較佳取代基係選自以下取代基:-OH、-O(C1
至C4
-烷基)、-SO3
H、經取代的C1
至C4
-烷基、未經取代的烷基、經取代的C1
至C4
烷氧基與未經取代的C1
至C4
烷氧基。
在通式(I)之較佳化合物中:R0
表示未經取代的C1
至C2
烷基,R1
表示經取代的C1
至C2
烷基或未經取代的C1
至C2
烷基、磺酸基、-CO-NH-(C1
至C2
烷基)或CN,R2
表示未經取代的C1
至C3
烷基,R3
表示H、磺酸基、未經取代的C1
至C2
烷基、未經取代的C1
至C2
烷氧基,R4
表示H、未經取代的C1
至C2
烷基、未經取代的C1
至C2
烷氧基,B 為具有分子式-CR5
R6
-的基團,其中R5
表示H、經取代的C1
至C9
烷基或未經取代的C1
至C9
烷基,R6
表示經取代的C1
至C9
烷基或未經取代的C1
至C9
烷基、未經取代的芳基或經取代的芳基或R5
與R6
一起形成五或六員環脂族環,其中該五或六員環係由C1
至C4
烷基取代或該五或六員環未經進一步取代。
在通式(I)之甚至更佳化合物中:R0
表示甲基,R1
表示-CH2
-SO3
H、或-CN,R2
表示甲基或乙基,R3
表示H、甲基、甲氧基或磺酸基,R4
表示H、甲基或甲氧基,B 為具有分子式-CR5
R6
-之基團,其中R5
表示H、甲基或乙基,R6
表示未經取代的C1
至C4
烷基、未經取代的芳基或經取代的芳基或R5
與R6
一起形成五或六員環脂族環,其中該六員環未經進一步取代。
在通式(I)之最佳化合物中:R0
表示甲基,R1
表示-CH2
-SO3
H或-CN,以-CH2
-SO3
H較佳,R2
表示乙基,R3
表示H、甲基、甲氧基或磺基,以H、甲基較佳,R4
表示H、甲基或甲氧基,以H較佳,B 為具有分子式-CR5
R6
-之基團,其中R5
表示H,R6
表示未經取代的芳基或經取代的芳基,以未經取代的芳基較佳,其中芳基為苯基。
結構式(I)化合物較佳具有結構式(I')
其中取代基具有以上所指的定義。
本發明亦提供一種製備結構式(I)化合物之方法。本發明之結構式(I)化合物可在常規條件下以常規方法製備。
在此等方法中,結構式(II)化合物之兩個胺基官能團(由文獻資料所知)
通常經重氮化及偶合至總共兩當量之結構式(III)化合物上
其中每個取代基分別如上定義。
在此等方法中,將特定二胺冷卻至0-10℃或較佳至0-5℃並且藉由添加亞硝基硫酸或亞硝酸鈉使其重氮化。其後,經雙-重氮化的二胺可與化合物(III)反應,較佳於水溶液中。
可藉由常用方法,將結構式(I)染料從反應媒介中分離出來,例如藉由鹼金屬鹽進行鹽析、過濾及乾燥,若適當時,在減壓及高溫下進行。
根據反應及/或分離條件,可呈游離酸、鹽或混合鹽獲得結構式(I)染料,該混合鹽包含例如一種或多種選自鹼金屬離子(例如鈉離子)、或銨離子或烷基銨陽離子(例如單-、二-或三甲基-或-乙基銨陽離子)的陽離子。本染料可藉由常用技術,由游離酸轉化為鹽或為混合鹽,或反之亦然,或由一種鹽轉化為另一種鹽。若需要,染料可藉由滲濾經進一步純化,在這種情況下,從陰離子染料粗產物中分離出不需要的鹽與合成副產物。
利用半透膜藉由施加壓力,自粗染料溶液中去除不需要的鹽與合成副產物及去除部份水,藉此得到不含不需要的鹽及合成副產物之染料的溶液,且若需要時以習知方式形成為固體。
結構式(I)之染料及其鹽特別適於將由天然或合成聚醯胺所組成之纖維材料染色或印刷成黃色至黃綠色調。結構式(I)之染料及其鹽適於製造噴墨印刷墨水,及利用此等噴墨印刷墨水印刷由天然或合成聚醯胺或纖維素(例如紙)所組成之纖維材料。
因此,本發明由另一態樣提供以結構式(I)染料、其鹽與混合物於染色及/或印刷由天然或合成聚醯胺所組成的纖維材料之用途。另一態樣為噴墨印刷墨水之製造及其用於印刷由天然或合成聚醯胺組成的纖維材料之用途。
染色係依據已知的方法進行,參見例如在Ullmannsder technischen Chemie,第四版,1982,22卷,658-673頁或Grundlagen der Textilveredlung,第十三版,1989,535-556頁及566-574頁,M. Peter與H.K. Rouette著的書中所述的染色方法。較佳染色法為在溫度30至140℃,更佳80至120℃及最佳80至100℃下,且液體比例在3:1至40:1範圍内之浸染法(exhaust process)。
待染色之基材可呈例如:紗、織物、迴圈形成之針織布或毯子之形式。甚至可能永久地於精細基材,例如羔羊毛、喀什米爾羊毛、羊駝毛與毛海上進行完全造型染色。本發明的染料特別適用於染色更細絲纖維(微纖維)。
根據本發明之染料及其鹽可與已知的酸染料高度相容。因此,結構式(I)染料、其鹽或混合物可單獨用於染色或印刷方法中,或者作為與其它同類酸染料(即,具有類似染色性質(如,例如耐久性與基材在染浴中之浸染率)的酸染料)之組合調染色或印刷組合物中的組分。本發明之染料尤其可與具有適宜發色團的某些其他染料一起使用。於組合調染色或印刷組合物中之染料比率係由需得到的色調決定。
如上所述,新穎的結構式(I)染料極適用於染色天然及合成聚醯胺(即羊毛、絲及所有尼龍類型),在其每一者上得到具有高耐久性,尤其係良好的耐光性與良好的耐濕性(沖洗、鹼性汗液)的染色。結構式(I)染料及其鹽具有高浸染率。結構式(I)染料及其鹽的上色能力同樣非常良好。在同一基材上的同色調染色之品質出衆。且,在人造光下所有染色具有一致色調。此外,耐蒸與耐煮性良好。
新穎染料之一決定性之優勢為其不含金屬且提供相當均勻的染色。
根據本發明之化合物可作為單獨染料,或者由於其良好的相容性,而作為與具有類似染色性質(例如就一般的耐久性、浸染值等而言)的其它同類染料的組合元素使用。得到的組合調染色具有與單一染料類似的染色耐久性。
本發明之結構式(I)染料亦可在三原色染色或印刷中作為黃色組分。三原色染色或印刷可利用所有常見且已知的染色與印刷法,例如連續法、上染法、泡沫染色法與噴墨法。
用於本發明方法的三原色染料混合物中單一染料組分之組成取決於所需色調。例如,褐色調較佳利用20-40重量%黃色組分、40-60重量%本發明橙色或紅色組分及10-20重量%藍色組分。
如上所述,黃色成份可包含單一組分或符合結構式(I)的不同橙色單獨組分之混合物。以兩種及三種組合較佳。
最佳的紅色及/或藍色組分分別說明於WO2002/46318或WO99/51681。
在以下實例中,份數與百分比係重量比,及溫度係以攝氏度表示。
根據已知方法,於0-5℃下,由13.8份(0.2mol)亞硝酸鈉於200份水與60份鹽酸(約30%)中,與26.8份(0.1mol)1,1-二-(4-胺苯基)-2-乙基-己烷進行四氮化反應。以30分鐘時間,將49.4份(0.2mol)如下結構式
化合物溶於250份水之溶液加入冰冷的四氮化溶液中。加入30% NaOH溶液,使pH值達到3-4.5,生成以下結構式染料
該染料藉由使用氯化鈉鹽析分離、過濾且在50℃下,於降壓下乾燥,或反應混合物可直接乾燥,無須分離產物。於羊毛且尤其聚醯胺纖維上可得到具有極佳耐光性及耐濕性之黃色染色(λmax
=445nm)。
下表I包含之染料可利用相應的初始材料,類似實例1所述之方法製得。此等染料於聚醯胺纖維及羊毛上提供具有極佳耐光性及耐濕性之黃色染色。λmax係以nm表示(奈米;於1%的乙酸溶劑中測得)。
將100份尼龍-6纖維加至包含2000份水、1份弱陽離子-活性均染劑(其基於乙氧基化胺丙基脂肪酸醯胺且對染料具有親和力)、0.25份製備實例1之染料且由1-2份40%乙酸調節至pH 5之40℃染缸中。40℃下10分鐘後,以1℃/分鐘之速率將該染缸加熱至98℃且保持沸騰45-60分鐘。此後在15分鐘内將其冷卻至70℃。從染缸中移出被染物,藉由熱水及隨後由冷水沖洗且乾燥。獲得的結果為具有良好耐光性及耐濕性的黃色聚醯胺染色。
將100份尼龍-6,6纖維加至包含2000份水、1份弱陽離子-活性均染劑(其基於乙氧基化胺丙基脂肪酸醯胺且對染料具有親和力)、0.3份製備實例1之染料且由1-2份40%乙酸調節至pH 5.5之40℃染缸中。40℃下10分鐘後,以1.5℃/分鐘之速率將該染缸加熱至120℃且在該溫度下保持15-25分鐘。此後在25分鐘内將其冷卻至70℃。從該染缸中移出被染物,藉由熱水及隨後由冷水沖洗且乾燥。獲得的結果為具有良好均染性之黃色聚醯胺染色,且其具有良好耐光性及耐濕性。
將100份羊毛纖維加至包含4000份水、1份弱兩性均染劑(其基於硫酸化、乙氧基化脂肪酸醯胺且對染料具有親和力)、0.4份製備實例1之染料且由1-2份40%乙酸調節至pH 5之40℃染缸中。40℃下10分鐘後,以1℃/分鐘之速率將該染缸加熱至沸騰且保持沸騰40-60分鐘。此後在20分鐘内將其冷卻至70℃。從該染缸中移出被染物,藉由熱水及隨後由冷水沖洗且乾燥。獲得的結果為具有良好耐光性及耐濕性的黃色羊毛染色。
使用50℃之包含以下組成之液體軋染100份尼龍-6編織材料:
40 份 製備實例1之染料
100 份 尿素
20 份 基於丁二醇的非離子增溶劑
15-20 份 乙酸(供調節pH至4)
10 份 弱陽離子-活性均染劑,其基於乙氧基化胺丙基脂肪酸醯胺且對染料具有親和力,及
810-815 份 水(其補充至1000份填充液體)
捲起所浸漬的材料,且於飽和蒸汽條件及85-98℃下,在蒸氣室中停留3-6小時以固色。然後,由熱水及冷水沖洗且乾燥染色。獲得的結果為具有良好件均染性、良好耐光性及耐濕性之黃色尼龍染色。
以液體軋染由尼龍-6組成且具有合成鹼纖維之紡織割絨片材,該液體每1000份包含:
1 份 製備實例1之染料
4 份 基於刺槐豆粉醚之可購得的增稠劑
2 份 較高碳數烷基酚的非離子環氧乙烷加成物
1 份 60%醋酸
然後以膏狀物印刷,該膏狀物每100份包含以下組分:
20 份 可購得的烷氧基化脂肪烷基胺(替代產物)
20 份 基於刺槐豆粉醚之可購得的增稠劑
印刷物在100℃下,於飽和蒸氣中固定6分鐘、經沖洗且乾燥。獲得的結果為具有黃色與白色圖案的顏色塗覆均勻之材料。
將100份編織尼龍-6,6纖維加至包含2000份水、1份弱陽離子-活性均染劑(其基於乙氧基化胺丙基脂肪酸醯胺且對染料具有親和力)、1.5份實例1之染料、0.2份專利申請案WO2002/46318中製備實例8之紅色染料:
及0.5份專利申請案WO99/51681與EP1066340 B1中製備實例46的藍色染料:
且由1-2份40%乙酸調節至pH 5之40℃染缸中。於40℃下10分鐘後,以1℃/分鐘之速率將該染缸加熱至98℃且保持沸騰45至60分鐘。此後在15分鐘内將其冷卻至70℃。從染缸中移出被染物,藉由熱水及隨後由冷水沖洗且乾燥。獲得的結果為具有良好耐光性及耐濕性的均勻灰色的聚醯胺染色。
55℃下,將100份經過鉻鞣與合成複鞣的修勻濕粒面皮革於含300份水與2份製備實例1之染料的染缸中染色30分鐘。添加4份含亞硫酸化魚油的60%乳液後,皮革脂液化45分鐘。然後,使用8.5%甲酸酸化且研磨10分鐘(染缸中的最終pH值為3.5-4.0)。隨後,沖洗該皮革,使其滴乾且照例經抛光。獲得的結果為染有均勻清晰的橙色調且具有良好耐性的皮革。
亦可藉由染料2至29進行應用實例A至G,得出相似的結果。
60℃下,將3份製備實例3之染料溶於82份軟化水與15份二乙二醇中。冷卻至室溫,得到橙色印刷墨水,其極適於在紙或聚醯胺與羊毛織物上進行噴墨印刷。
亦可藉由染料1或2與4至29進行應用實例H,得出相似的結果。
在10分鐘内,將包含1000份水、80份經煅燒的無水硫酸鈉、1份硝基苯-3-磺酸鈉與1份實例1染料之染缸加熱至80℃。然後添加100份絲光棉。隨後,於80℃下染色5分鐘,然後在15分鐘内加熱至95℃。95℃下10分鐘後,添加3份碳酸鈉,95℃下,20分鐘後進一步添加7份碳酸鈉及30分鐘後另添加10份碳酸鈉。隨後在95℃下,繼續染色60分鐘。然後將已染色材料從染缸中移除,且在流動的軟化水中沖洗3分鐘。隨後進行兩次清洗,每次於5000份煮沸的軟化水中進行10分鐘,然後在60℃下,於流動的軟化水中沖洗3分鐘,及以冷自來水沖洗1分鐘。乾燥,得到具有良好耐性的亮黃色棉染色。
將0.2份製備實例1之染料溶於100份熱水中且將該溶液冷卻至室溫。將該溶液加至含於打漿機中之含100份化學漂白的亞硫酸紙漿的2000份水中。混合15分鐘後,以常規方式,利用樹脂膠料與硫酸鋁為原料上膠。由該原料製得的紙具有良好耐濕性的黃色調。
亦可藉由染料2至29進行應用實例I與J,得出相似的結果。
Claims (8)
- 一種通式(I)之化合物,
- 如請求項1之化合物,其特徵在於該等結構式(I)之化合物帶有至少一個陰離子取代基。
- 如請求項2之化合物,其特徵在於:R0 表示未經取代的C1 至C2 烷基,R1 表示經取代的C1 至C2 烷基或未經取代的C1 至C2 烷基、磺酸基、-CO-NH-(C1 至C2 烷基)或CN,R2 表示未經取代的C1 至C3 烷基,R3 表示H、磺酸基、未經取代的C1 至C2 烷基、未經取代的C1 至C2 烷氧基,R4 表示H、未經取代的C1 至C2 烷基、未經取代的C1 至C2 烷氧基,B 為具有式-CR5 R6 -的基團,其中R5 表示H、經取代的C1 至C9 烷基或未經取代的C1 至C9 烷基,R6 表示經取代的C1 至C9 烷基或未經取代的C1 至C9 烷基、未經取代的芳基或經取代的芳基或R5 與R6 一起形成五或六員環脂族環,其中該五或六員環係經C1 至C4 烷基取代或該五或六員環未經進一步取代。
- 如請求項3之化合物,其特徵在於R0 表示甲基,R1 表示-CH2 -SO3 H、或-CN, R2 表示甲基或乙基,R3 表示H、甲基、甲氧基或磺酸基,R4 表示H、甲基或甲氧基,B 為具有式-CR5 R6 -之基團,其中R5 表示H、甲基或乙基,R6 表示未經取代的C1 至C4 烷基、未經取代的芳基或經取代的芳基或R5 與R6 一起形成六員環脂族環,其中該六員環未經進一步取代。
- 一種製備如請求項1之結構式(I)化合物之方法,其特徵在於使結構式(II)化合物中之兩個胺官能團
- 一種以如請求項1之結構式(I)化合物用於染色及/或印刷有機基材之用途。
- 一種以如請求項1之結構式(I)化合物用於染色及/或印刷羊毛、絲及合成聚醯胺之用途。
- 一種以如請求項1之結構式(I)化合物用於製備供噴墨方 法用的印刷墨水之用途。
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2009
- 2009-06-30 TW TW098122064A patent/TWI461408B/zh active
- 2009-06-30 TW TW098122066A patent/TWI588214B/zh active
- 2009-07-01 CN CN2009801247526A patent/CN102076780B/zh active Active
- 2009-07-01 EP EP09772480A patent/EP2307510B1/en active Active
- 2009-07-01 MX MX2010014525A patent/MX2010014525A/es active IP Right Grant
- 2009-07-01 BR BRPI0914939-2A patent/BRPI0914939B1/pt active IP Right Grant
- 2009-07-01 EP EP09772479A patent/EP2307509B1/en active Active
- 2009-07-01 JP JP2011515453A patent/JP2011526636A/ja active Pending
- 2009-07-01 JP JP2011515452A patent/JP2011526635A/ja active Pending
- 2009-07-01 WO PCT/EP2009/058264 patent/WO2010000780A1/en active Application Filing
- 2009-07-01 ES ES09772479T patent/ES2383580T3/es active Active
- 2009-07-01 PT PT09772480T patent/PT2307510E/pt unknown
- 2009-07-01 KR KR1020117002373A patent/KR101760661B1/ko active IP Right Grant
- 2009-07-01 MX MX2010014526A patent/MX2010014526A/es active IP Right Grant
- 2009-07-01 ES ES09772480T patent/ES2383581T3/es active Active
- 2009-07-01 WO PCT/EP2009/058262 patent/WO2010000779A1/en active Application Filing
- 2009-07-01 CN CN2009801247511A patent/CN102076779B/zh active Active
- 2009-07-01 PT PT09772479T patent/PT2307509E/pt unknown
- 2009-07-01 BR BRPI0913833-1A patent/BRPI0913833B1/pt active IP Right Grant
- 2009-07-01 KR KR1020117002376A patent/KR101649484B1/ko active IP Right Grant
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2014
- 2014-09-18 JP JP2014190261A patent/JP2015038264A/ja active Pending
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US3979378A (en) * | 1970-01-31 | 1976-09-07 | Badische Anilin- & Soda-Fabrik Aktiengesellschaft | Water-soluble azo dyes having a substituted 2-hydroxypyridone (6) coupling component |
Also Published As
Publication number | Publication date |
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KR20110031359A (ko) | 2011-03-25 |
CN102076779A (zh) | 2011-05-25 |
ES2383581T3 (es) | 2012-06-22 |
PT2307509E (pt) | 2012-04-12 |
BRPI0913833A2 (pt) | 2015-10-20 |
PT2307510E (pt) | 2012-04-12 |
WO2010000780A1 (en) | 2010-01-07 |
CN102076780B (zh) | 2013-08-21 |
TW201012802A (en) | 2010-04-01 |
MX2010014526A (es) | 2011-02-22 |
MX2010014525A (es) | 2011-02-22 |
CN102076780A (zh) | 2011-05-25 |
KR101649484B1 (ko) | 2016-08-19 |
JP2015038264A (ja) | 2015-02-26 |
KR20110039542A (ko) | 2011-04-19 |
JP2011526636A (ja) | 2011-10-13 |
BRPI0914939A2 (pt) | 2015-10-20 |
CN102076779B (zh) | 2013-08-21 |
BRPI0913833B1 (pt) | 2018-06-12 |
JP2011526635A (ja) | 2011-10-13 |
ES2383580T3 (es) | 2012-06-22 |
KR101760661B1 (ko) | 2017-07-24 |
TW201005043A (en) | 2010-02-01 |
WO2010000779A1 (en) | 2010-01-07 |
EP2307509A1 (en) | 2011-04-13 |
BRPI0914939B1 (pt) | 2018-06-19 |
EP2307510A1 (en) | 2011-04-13 |
EP2307509B1 (en) | 2012-02-29 |
EP2307510B1 (en) | 2012-02-29 |
TWI588214B (zh) | 2017-06-21 |
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