TWI618752B - 分散偶氮染料,其製備方法及其用途 - Google Patents
分散偶氮染料,其製備方法及其用途 Download PDFInfo
- Publication number
- TWI618752B TWI618752B TW102126639A TW102126639A TWI618752B TW I618752 B TWI618752 B TW I618752B TW 102126639 A TW102126639 A TW 102126639A TW 102126639 A TW102126639 A TW 102126639A TW I618752 B TWI618752 B TW I618752B
- Authority
- TW
- Taiwan
- Prior art keywords
- formula
- patent application
- scope
- dye
- item
- Prior art date
Links
- 0 Cc(c(C(N1*)=O)c(cc2*)C1=O)c2N=N[Al] Chemical compound Cc(c(C(N1*)=O)c(cc2*)C1=O)c2N=N[Al] 0.000 description 2
Classifications
-
- 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
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0033—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with one nitrogen atom
-
- 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
-
- 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
- C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
-
- 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
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0048—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a six-membered heterocyclic ring with one nitrogen atom
-
- 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
-
- 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
- C09B29/0805—Amino benzenes free of acid groups
-
- 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
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
-
- 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
- C09B29/095—Amino naphthalenes
-
- 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
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3639—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more amino groups
-
- 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
- C09B29/3691—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing nitrogen and sulfur as heteroatom
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
- C09B43/42—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms by substituting radicals containing hetero atoms for —CN radicals
-
- 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
-
- 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
-
- 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
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
-
- D—TEXTILES; PAPER
- D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B2331/00—Fibres made from polymers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polycondensation products
- D10B2331/04—Fibres made from polymers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polycondensation products polyesters, e.g. polyethylene terephthalate [PET]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
本發明係關於下式之偶氮染料
其中R1表示C1-C12烷基,其未經取代或由一或多個C1-C12烷氧基、羥基、胺基、氰基或鹵素原子取代,且其可雜有基團-O-、-S-、-NR4-、-COO-或-OOC-一或多次;R4為氫或C1-C12烷基;R2為氰基且R3為鹵素,或R2為鹵素且R3為氰基;及Ar表示碳環或雜環芳基,其製備方法、含有該等染料之混合物及其在對半合成及尤其合成疏水性纖維材料,更尤其紡織材料進行染色或印花中之用途。
Description
本發明係關於基於胺基鄰苯二甲醯亞胺作為重氮化成分之分散偶氮染料、此類染料之製備方法及其在對半合成及尤其合成疏水性纖維材料,更尤其紡織材料進行染色或印花中之用途。
基於胺基鄰苯二甲醯亞胺作為重氮化成分之偶氮染料為自例如美國專利第3,980,634號中已知。然而,已發現使用目前已知染料所獲得之染色品或印花不能在所有情況下滿足如今需求,尤其對於耐光堅牢度及耐洗滌堅牢度而言。因此,需要尤其具有良好耐洗滌堅牢度特性之新穎染料。
意外地,吾等發現基於特定經鹵素取代及經氰基取代之鄰苯二甲醯亞胺之偶氮染料顯示極好的耐光堅牢度及極佳的耐洗滌堅牢度結果。
本發明係關於式(1)染料
其中
R1表示C1-C12烷基,其未經取代或由一或多個C1-C12烷氧基、C1-C12烷基羰基、C7-C25芳基羰基、羥基、胺基、氰基或鹵素原子取代,且其可雜有基團-O-、-S-、-NR4-、-COO-或-OOC-一或多次;R4為氫或C1-C12烷基;R2為氰基且R3為鹵素,或R2為鹵素且R3為氰基;及Ar表示碳環或雜環芳基。
表示烷基之任何基團可為直鏈或分支鏈烷基。
烷基之實例包括甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、異戊基、新戊基、正己基、正辛基、異辛基、正癸基及正十二烷基。
舉例而言,C1-C12烷氧基可為甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、第二丁氧基、第三丁氧基、正戊氧基、新戊氧基、正己氧基、正辛氧基、異辛氧基、正癸氧基或正十二烷氧基。
表示鹵素之任何基團可為氟、氯或溴,詳言之氯或溴。
用於製備偶氮染料之碳環或雜環芳族偶合成分Ar-H為熟習此項技術者所熟知。
適合基團Ar為苯、萘、二氫吡唑酮、噻吩、噻唑、喹啉或6-羥基吡啶酮-(2)系之偶合成分之基團。
優先考慮式(1)偶氮染料,其中R1表示未經取代之C1-C12烷
基。
式(1)偶氮染料尤其較佳,其中R1表示甲基、乙基、正丙基、異丙基或正丁基。
在最佳式(1)偶氮染料中,R1為乙基。
Ar較佳為下式之基團:
其中R5表示氫、氯、甲基、甲氧基、2-羥乙基或-COOR19,其中R19具有以上對於R1所給出含義中之一種;R6為氫、羥基、氯、三氟甲基、-OR20、-OCH2COOR20、-NH-CO-R20或-NH-SO2-R20,其中R20具有以上對於R1所給出含義中之一種;R7及R8各自彼此獨立地具有以上對於R1所給出含義中之一種;
X表示伸乙基、伸丙基或氧伸乙基;R9為乙烯基、烯丙基、苄基,或具有以上對於R1所給出含義中之一種;R10為羥基或苯胺基;R11為氫、-COOR21或C6-C24芳基,其未經取代或由一或多個C1-C12烷基、C1-C12烷氧基、羥基、胺基、氰基或鹵素原子取代;R21具有以上對於R1所給出含義中之一種;R12為氫或-SO2-NHR22,其中R22具有以上對於R1所給出含義中之一種;R13為氫或羥基;R14表示C1-C12烷基或三氟甲基;R15為氰基或-CONH2;R16具有以上對於R1所給出含義中之一種;R23及R24各自彼此獨立地為氫、乙烯基、烯丙基或C1-C6烷基,其未經取代或由氰基、羧基、羥基、C1-C6烷氧基-、C2-C8烷氧基烷氧基-或C6-C24芳基取代;及R18為氫、C1-C12烷基、C1-C12烷氧基或C6-C24芳基,其未經取代或由一或多個C1-C12烷基、C1-C12烷氧基、羥基、胺基、氰基或鹵素原子取代。
尤其較佳為如上文所定義之式(1)染料,其中Ar為式(2a)基團。
進一步優先考慮式(1)偶氮染料,其中Ar為式(2a)基團,其中R6為-NH-CO-R20且R20為如上文所定義。
在式(2a)中,R7及R8各自彼此獨立地較佳表示甲基、乙基、正丙基、正丁基、烯丙基、苄基、4-硝基苄基、4-甲氧基苄基、3-甲氧基苄
基、2-羥乙基、2-乙醯氧基乙基、2-氰基乙基、2-甲氧基乙基、2-苯乙基、1-甲氧基羰基乙基、2-甲氧基羰基乙基、甲氧基羰基甲基、1-乙氧基羰基乙基、2-乙氧基羰基乙基、乙氧基羰基甲基、2-羥基-3-苯氧基丙基、2-羥基-3-異丙氧基丙基或下式基團:
此外,優先考慮式(1)偶氮染料,其中Ar為式(2a)基團,其中R5為氫、甲基或甲氧基。
本發明亦關於一種如技術方案第1項之式(1)偶氮染料的製備方法,其包含使式(3)偶氮染料
其中R1及Ar為如上文所定義且Hal表示鹵素,與至少一種鹼金屬氰化物與至少一種重金屬氰化物之混合物反應,其中每莫耳式(3)染料施用總量為0.30mol至1.25mol之氰化物。
式(3)染料可自例如美國專利第3,980,634號已知,或可根據已知方法製備。
二溴化合物之鹵素/氰基交換產生所主張的式(1)染料,其本身同樣可自WO 2002/068539已知。
出乎意料地,鹼金屬氰化物與重金屬氰化物之混合物的施用使得反應限於部分氰基置換;亦即僅產生少量二氰基化合物。
反應較佳在非質子極性溶劑中,如DMF、DMAc、NMP、NEP、DMSO、四甲脲、環丁碸、HMPT、吡啶及吡啶衍生物,以及在兩種或兩種以上非質子極性溶劑之混合物中進行。
氰化試劑為至少一種鹼金屬氰化物(如NaCN或KCN)與至少一種重金屬氰化物(如CuCN)之混合物。鹼金屬氰化物/重金屬氰化物之莫耳比較佳為1:20至1:1,詳言之為1:15至1:5。
有目的地按如下量施用氰化物混合物:每莫耳式(3)染料氰化物之總量為0.25至1.25mol,較佳為0.4至1.0mol。
視二鹵化合物(3)之活性而定,反應溫度可在寬範圍內變化。反應較佳在0℃至150℃之溫度下進行,更佳為室溫至130℃,且詳言之為室溫至60℃。
由式(3)染料與氰化物混合物反應獲得之反應產物含有作為主產物之式(1a)染料,及視反應條件(溶劑、反應時間、溫度、離析物之比)而定,少量式(1b)異構染料以及式(3)離析物,及式(4)二氰基化合物
對於在紡織纖維方面之染料應用而言,不需要將主產物(1a)與其他染料分離,此係因為作為原始產物所獲得之染料混合物同樣具有極好的積色(build-up)特性,且提供展示高纖維勻染度及表面勻染度之聚酯染色品。
因此,本發明亦關於一種混合物,包含式(1)偶氮染料
式(3)偶氮染料
式(4)偶氮染料
其中R1及Ar為如申請專利範圍第1項中所定義,且Hal表示鹵素,尤其溴。
為了調整特定的色調,將兩種或兩種以上不同式(1)染料合併為可取的。
因此,本發明進一步關於一種染料混合物,包含(A)10至90wt.%,較佳20至80wt.%如上文所定義之式(1)染料,及(B)10至90wt.%,較佳20至80wt.%如上文所定義之式(1)染料,其結構上不同於根據成分(A)之染料。
根據本發明之偶氮染料及染料混合物亦可連同其他染料一起令人滿意地用於製備混合色調。
可有利地與根據本發明之式(1)染料混合的另外適合染料為例如C.I.分散紫(Disperse Violet)107、C.I.分散藍(Disperse Blue)60、C.I.分散藍284、C.I.分散藍295、C.I.分散藍337、C.I.分散藍354、C.I.分散藍365、C.I.分散藍368、C.I.分散藍378、C.I.分散藍380以及WO 2009/013122中所揭示之藍色染料。
根據本發明之偶氮染料及染料混合物可尤其用作雙色或
三色染色或印花技術中之適合成分。
因此,本發明進一步關於一種雙色或三色染料混合物,包含至少一種如申請專利範圍第1項之式(1)偶氮染料及至少一種另外分散染料。
根據本發明之染料及染料混合物可用於對半合成及尤其合成疏水性纖維材料,更尤其紡織材料進行染色或印花。由包含此類半合成或合成疏水性纖維材料之混紡織物構成的紡織材料亦可使用根據本發明之染料進行染色或印花。
所考慮之半合成纖維材料尤其為21/2-乙酸纖維素及三乙酸纖維素。
合成疏水性纖維材料尤其由以下各者組成:線性芳族聚酯,例如對苯二甲酸及二醇類之彼等,尤其乙二醇,或對苯二甲酸與1,4-雙(羥甲基)環己烷之縮合產物;聚碳酸酯,例如α,α-二甲基-4,4-二羥基-二苯基甲烷及光氣之彼等;及基於聚氯乙烯或聚醯胺之纖維。
根據本發明之染料及染料混合物施用於纖維材料已根據已知染色方法實現。舉例而言,在慣用陰離子或非離子分散劑及視情況選用之慣用溶脹劑(載體(carrier))存在下,在80至140℃之溫度下,聚酯纖維材料在排氣製程(exhaust process)中自水性分散液染色。21/2-乙酸纖維素較佳在65至85℃下染色,且三乙酸纖維素較佳在65至115℃之溫度下染色。
根據本發明之染料及染料混合物不會使同時存在於染浴中之羊毛及棉著色,或使此類材料僅稍微著色(極好保留(reservation)),
以使得其亦可令人滿意地用於聚酯/羊毛及聚酯/纖維素纖維混紡織物之染色。
根據本發明之染料及染料混合物適於在排氣製程中根據熱熔製程(thermosol process)之染色且適於印花法。
在此類方法中,該等纖維材料可呈多種加工形式,例如呈纖維、紗線,或非編織物、編織物或針織物之形式。
有利地在使用前將根據本發明之染料及染料混合物轉化為染料製劑。出於此目的,研磨染料,以使其粒度平均為0.1至10微米。研磨可在分散劑存在下進行。舉例而言,將乾燥染料連同分散劑一起研磨,或連同分散劑一起揉合成糊狀物形式,且隨後在真空中或藉由原子霧化(atomisation)乾燥。添加水之後,所得製劑可用於製備印花糊及染浴。
對於印花,可使用慣用增稠劑,例如經修飾或未經修飾之天然產物,例如海藻酸鹽、大英粉(British gum)、阿拉伯膠、結晶膠、刺槐豆粉、黃蓍膠、羧甲基纖維素、羥乙基纖維素、澱粉;或合成產物,例如聚丙烯醯胺、聚丙烯酸或其共聚物或聚乙烯醇。
根據本發明之式(1)染料亦適合作為著色劑用於記錄系統中。此類記錄系統為例如用於紙或織物印刷之市售噴墨列印機,或諸如鋼筆或原子筆之書寫工具,且尤其噴墨列印機。出於彼目的,根據本發明之染料首先形成適合用於記錄系統之形式。適合形式為例如水性墨,其包含作為著色劑之根據本發明之染料。藉由與獨立成分混合在一起,必要時與適合分散劑組合,可在所需量之水中以慣用方式製備墨水。
根據本發明之染料及染料混合物賦予該等材料(尤其聚酯
材料)均勻的色調,具有極好的耐用堅牢度特性,尤其諸如,良好的耐光堅牢度、耐熱定型堅牢度、耐褶堅牢度、耐氯堅牢度及耐濕堅牢度,例如耐水堅牢度、耐汗漬堅牢度及耐洗滌堅牢度;藉由極好的耐摩擦堅牢度進一步表徵完成之染色品。應特別強調,所獲得之染色品關於汗漬及尤其關於洗滌之良好的堅牢度特性。
此外,根據本發明之染料及染料混合物亦非常適合於自超臨界CO2對疏水性纖維材料進行染色。
本發明係關於以上所提及之根據本發明之染料的用途,以及關於對半合成或合成疏水性纖維材料,尤其紡織材料進行染色或印花之方法,在該方法中將根據本發明之染料施用於該等材料或併入其中。該等疏水性纖維材料較佳為紡織聚酯材料。另外基板可藉由本發明之方法及較佳方法條件處理,其可見於上文關於根據本發明之染料的用途更詳細的描述中。
在噴墨列印法之情況下,將獨立的墨液滴自噴嘴以受控制之方式噴射至基板上。用於彼目的之方法主要為連續噴墨法及按需滴墨法。在連續噴墨法之情況下,液滴連續地產生,印刷操作所不需之液滴被排出至容器中且再循環。在按需滴墨法之情況下,另一方面,液滴視需要產生且用於印刷;也就是說,液滴僅在需要用於印刷操作時產生。舉例而言,藉助於壓電噴墨頭或藉由熱能(噴泡),可產生液滴。優先考慮藉助於壓電噴墨頭之印刷及根據連續噴墨法之印刷。
本發明因此亦關於水性墨,其包含根據本發明之式(1)染料,且關於此類墨水在噴墨印刷法中之用途,其用於對多種基板進行印刷,
尤其紡織纖維材料,上文所指出之定義及偏好應用於染料、墨水及基板。
本發明亦關於藉由該方法染色或印花之疏水纖維材料,較佳為聚酯紡織材料。
此外,根據本發明之染料適合於現代複製方法,例如熱轉移印花。
以下實施例用來說明本發明。除非外指明,否則其中份數為重量份,且百分比為重量百分比。溫度以攝氏度形式提供。重量份與體積份之間的關係與公克與立方公分之間的關係相同。
I.製備實施例
I.1式(101)染料
於室溫(RT)下,於120ml吡啶中攪拌下溶解8.48g(0.015mol)之式(101a)染料,
其如US 3,980,634中所描述而製備。向100ml吡啶中提供0.147g(0.003mol)細粉狀NaCN及1.343g(0.003mol)細粉狀CuCN,且在劇烈攪拌下懸浮。於室溫下,在4h內向式(201)染料之溶液中緩慢滴加由此獲得之懸浮液。攪拌反應混合物隔夜,且隨後用150ml吡啶稀釋。濾出藍色沈澱,且用水洗滌;乾燥之後獲得2g粗產物。
根據HPLC分析,原始產物基本上由三種不同染料之混合物組成,即約30%離析物(201)、50%式(101)染料及20%式(202)二氰基化合物,藉由習知層析方法將染料分離。
熔點(melting point;m.p.)=156℃至158℃
λmax=472nm(λmax=最大吸收波長)
m.p.=204℃至208℃
λmax =586nm
1H-NMR(DMSO-d6)250MHz):δ=9.39(s,寬峰,-NH),8.17(s,寬峰,1H),8.06(d,寬峰,J=2.0,1H),8.03(s,1H),6.53(d,寬峰,J=4.0,1H),3.79(q,J=3.0,2H),3.57(q,J=3.0,4H),2.22(s,3H),1.23-1.35(m,9H)。
m.p.=128℃至131℃
λmax=608nm
以下表1及表2中所列之式(102)至(457)染料可以與上述方法類似之方法製備。
II.應用實施例
II.1:聚酯之染色
研磨實施例I.1中製備之1重量份式(101)染料連同4份市售分散劑及15份水。使用彼調配物,在135℃下藉由高溫排氣製程,在編織聚酯上產生1%染色(基於染料及基板)。
測試結果:染色耐光堅牢度極佳,以及在AATCC 61及ISO 105測試中結果極佳。染料之積色特性極好。
II.2:聚酯之染色
藉由使用式(102)至(186)染料代替式(101)染料,重複實施例II.1。染料之積色特性極好,且染色品展現良好的耐光堅牢度及在AATCC 61及ISO 105測試中之極好結果。
Claims (14)
- 一種式(1)偶氮染料
- 如申請專利範圍第1項之式(1)偶氮染料,其中R1表示未經取代之C1-C12烷基。
- 如申請專利範圍第1項之式(1)偶氮染料,其中R1表示甲基、乙基、正丙基、異丙基或正丁基。
- 如申請專利範圍第1項至第3項中任一項之式(1)偶氮染料,其中R2為氰基,且R3為溴。
- 如申請專利範圍第1項至第3項中任一項之式(1)偶氮染料,其中Ar為下式之基團:
- 如申請專利範圍第5項之式(1)偶氮染料,其中Ar為該式(2a)基團,其中R6為-NH-CO-R20。
- 如申請專利範圍第5項之式(1)偶氮染料,其中Ar為該式(2a)基團,其中R7及R8各自彼此獨立地為甲基、乙基、正丙基、正丁基、烯丙基、苄基、4-硝基苄基、4-甲氧基苄基、3-甲氧基苄基、2-氰基乙基、2-甲氧基乙基、2-苯乙基、1-甲氧基羰基乙基、2-甲氧基羰基乙基、甲氧基羰基甲基、1-乙氧基羰基乙基、2-乙氧基羰基乙基、乙氧基羰基甲基、2-羥基-3-苯氧基丙基或2-羥基-3-異丙氧基丙基。
- 如申請專利範圍第5項之式(1)偶氮染料,其中Ar為該式(2a)基團,其中R5為氫、甲基或甲氧基。
- 一種如申請專利範圍第1項之式(1)偶氮染料之製備方法,其包含使式(3)偶氮染料
- 一種混合物,包含式(1)偶氮染料
- 一種雙色或三色染料混合物,包含至少一種如申請專利範圍第1項之式(1)偶氮染料及至少一種另外分散染料。
- 一種用於對半合成或合成疏水性纖維材料進行染色或印花之方法,在該方法中將如申請專利範圍第1項之式(1)染料施用於該等材料或併入其中。
- 一種如申請專利範圍第1項之式(1)染料之用途,其用於對半合成及尤其 合成疏水性纖維材料,更尤其紡織材料進行染色或印花。
- 一種半合成或尤其合成疏水性纖維材料,更尤其紡織材料,其藉由如申請專利範圍第12項之方法進行染色或印花。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12178163 | 2012-07-27 | ||
??12178163.7 | 2012-07-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW201422726A TW201422726A (zh) | 2014-06-16 |
TWI618752B true TWI618752B (zh) | 2018-03-21 |
Family
ID=48699790
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW102126639A TWI618752B (zh) | 2012-07-27 | 2013-07-25 | 分散偶氮染料,其製備方法及其用途 |
Country Status (14)
Country | Link |
---|---|
US (2) | US9376570B2 (zh) |
EP (1) | EP2877628B1 (zh) |
JP (1) | JP2015528043A (zh) |
KR (1) | KR102146686B1 (zh) |
CN (1) | CN104520498B (zh) |
BR (1) | BR112015000019B8 (zh) |
ES (1) | ES2955346T3 (zh) |
HK (1) | HK1211063A1 (zh) |
IN (1) | IN2014DN08994A (zh) |
MX (1) | MX368843B (zh) |
PL (1) | PL2877628T3 (zh) |
PT (1) | PT2877628T (zh) |
TW (1) | TWI618752B (zh) |
WO (1) | WO2014016072A1 (zh) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104448892B (zh) * | 2014-11-18 | 2017-04-05 | 李百春 | 一种高水洗牢度和升华牢度的宝蓝分散染料及其制备方法 |
CN104479393A (zh) * | 2014-11-18 | 2015-04-01 | 昌邑福莱蒽特精细化工有限公司 | 高水洗牢度和升华牢度的大红色分散染料及其制备方法 |
CN104448894B (zh) * | 2014-11-18 | 2016-08-24 | 昌邑福莱蒽特精细化工有限公司 | 高水洗牢度和升华牢度的分散绿光蓝染料及其制备方法 |
CN104479395A (zh) * | 2014-11-18 | 2015-04-01 | 杭州福莱蒽特精细化工有限公司 | 一种高水洗牢度和高日晒牢度的分散染料及其制备方法 |
CN104448893B (zh) * | 2014-11-18 | 2017-04-05 | 杭州福莱蒽特精细化工有限公司 | 一种高水洗牢度和升华牢度的红色分散染料及其制备方法 |
CN104403348B (zh) * | 2014-11-18 | 2016-09-07 | 李百春 | 一种高水洗牢度和升华牢度的紫色分散染料及其制备方法 |
CN105038316A (zh) * | 2015-07-25 | 2015-11-11 | 大连理工大学 | 杂环偶氮分散染料及其制备方法 |
CN105647224A (zh) * | 2016-01-28 | 2016-06-08 | 俞杏英 | 一种邻苯二甲酰亚胺-偶氮分散染料单体化合物及其制备方法和应用 |
TWI707002B (zh) * | 2016-05-25 | 2020-10-11 | 瑞士商杭斯曼高級材料公司 | 分散偶氮染料、其製備方法及其用途 |
CN107129706B (zh) * | 2017-05-02 | 2019-05-17 | 杭州福莱蒽特精细化工有限公司 | 一种高染色牢度的分散深蓝染料组合物 |
PL3645632T3 (pl) | 2017-06-28 | 2023-07-31 | Huntsman Textile Effects (Switzerland) Gmbh | Dyspersyjne barwniki azowe |
CN109054429B (zh) * | 2018-07-06 | 2020-06-09 | 浙江万丰化工股份有限公司 | 一种含乙酰胺基团的偶氮染料化合物及其制备方法和应用 |
CN108864732B (zh) * | 2018-07-06 | 2020-05-05 | 浙江万丰化工股份有限公司 | 一种含甲磺酰胺基团的偶氮染料化合物及其制备方法和应用 |
KR102124602B1 (ko) | 2018-07-16 | 2020-06-18 | 한국화학연구원 | 초임계 유체염색용 아조계 분산염료 및 그의 합성법 |
KR102124599B1 (ko) | 2018-07-16 | 2020-06-18 | 한국화학연구원 | 초임계 유체염색용 아조계 분산염료 및 그의 합성법 |
KR102174800B1 (ko) | 2019-03-21 | 2020-11-05 | 충남대학교산학협력단 | 초임계 유체 염색용 안트라퀴논 염료 및 이를 이용한 폴리에스테르 섬유의 초임계 유체 염색 방법 |
KR102195418B1 (ko) | 2019-03-21 | 2020-12-29 | 충남대학교산학협력단 | 초임계 유체 염색용 분산 염료 및 이를 이용한 나일론 섬유의 초임계 유체 염색 방법 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6555664B1 (en) * | 1998-12-31 | 2003-04-29 | Ciba Specialty Chemicals Corporation | Phthalimidyl azo pigments, method for producing same and utilisation thereof |
WO2007082803A1 (en) * | 2006-01-18 | 2007-07-26 | Ciba Holding Inc. | Process for the treatment of fiber materials |
WO2010046192A2 (en) * | 2008-10-21 | 2010-04-29 | Huntsman Advanced Materials (Switzerland) Gmbh | Azo dyes, a process for the preparation thereof and the use thereof |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3980634A (en) | 1973-07-02 | 1976-09-14 | Eastman Kodak Company | Phthalimidyl-azo aniline type compounds and polyester fibers dyed therewith |
US4012372A (en) * | 1973-07-02 | 1977-03-15 | Eastman Kodak Company | Phthalimidyl-azo-tetrahydro-quinoline compounds |
WO2002068539A1 (en) | 2001-02-07 | 2002-09-06 | Ciba Specialty Chemicals Holding Inc. | Phthalimidyl azo dyes, process for the preparation thereof and the use thereof |
CN101370923B (zh) * | 2006-01-18 | 2012-01-11 | 西巴控股公司 | 处理纤维材料的方法 |
EP2167496B1 (en) | 2007-07-20 | 2014-09-24 | Huntsman Advanced Materials (Switzerland) GmbH | Azo dyes |
-
2013
- 2013-06-26 US US14/413,583 patent/US9376570B2/en active Active
- 2013-06-26 PL PL13731767.3T patent/PL2877628T3/pl unknown
- 2013-06-26 JP JP2015523473A patent/JP2015528043A/ja active Pending
- 2013-06-26 IN IN8994DEN2014 patent/IN2014DN08994A/en unknown
- 2013-06-26 BR BR112015000019A patent/BR112015000019B8/pt active IP Right Grant
- 2013-06-26 PT PT137317673T patent/PT2877628T/pt unknown
- 2013-06-26 KR KR1020157005020A patent/KR102146686B1/ko active IP Right Grant
- 2013-06-26 CN CN201380039712.8A patent/CN104520498B/zh active Active
- 2013-06-26 MX MX2015000949A patent/MX368843B/es active IP Right Grant
- 2013-06-26 WO PCT/EP2013/063346 patent/WO2014016072A1/en active Application Filing
- 2013-06-26 EP EP13731767.3A patent/EP2877628B1/en active Active
- 2013-06-26 ES ES13731767T patent/ES2955346T3/es active Active
- 2013-07-25 TW TW102126639A patent/TWI618752B/zh active
-
2015
- 2015-12-02 HK HK15111818.0A patent/HK1211063A1/zh unknown
-
2016
- 2016-05-11 US US15/151,624 patent/US10023742B2/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6555664B1 (en) * | 1998-12-31 | 2003-04-29 | Ciba Specialty Chemicals Corporation | Phthalimidyl azo pigments, method for producing same and utilisation thereof |
WO2007082803A1 (en) * | 2006-01-18 | 2007-07-26 | Ciba Holding Inc. | Process for the treatment of fiber materials |
WO2010046192A2 (en) * | 2008-10-21 | 2010-04-29 | Huntsman Advanced Materials (Switzerland) Gmbh | Azo dyes, a process for the preparation thereof and the use thereof |
Also Published As
Publication number | Publication date |
---|---|
ES2955346T3 (es) | 2023-11-30 |
CN104520498A (zh) | 2015-04-15 |
PL2877628T3 (pl) | 2023-12-27 |
US20160251517A1 (en) | 2016-09-01 |
WO2014016072A1 (en) | 2014-01-30 |
MX368843B (es) | 2019-10-17 |
US9376570B2 (en) | 2016-06-28 |
PT2877628T (pt) | 2023-09-11 |
JP2015528043A (ja) | 2015-09-24 |
KR102146686B1 (ko) | 2020-08-24 |
KR20150038400A (ko) | 2015-04-08 |
IN2014DN08994A (zh) | 2015-05-22 |
MX2015000949A (es) | 2015-04-16 |
BR112015000019A2 (pt) | 2017-06-27 |
EP2877628A1 (en) | 2015-06-03 |
HK1211063A1 (zh) | 2016-05-13 |
BR112015000019B1 (pt) | 2021-12-07 |
US20150197637A1 (en) | 2015-07-16 |
CN104520498B (zh) | 2018-01-16 |
TW201422726A (zh) | 2014-06-16 |
BR112015000019B8 (pt) | 2023-05-16 |
EP2877628B1 (en) | 2023-07-12 |
US10023742B2 (en) | 2018-07-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI618752B (zh) | 分散偶氮染料,其製備方法及其用途 | |
TWI661009B (zh) | 分散染料混合物,彼之製備及用途 | |
KR101346852B1 (ko) | 고 습윤견뢰도의 흑색 및 네이비블루 분산염료 조성물 | |
KR20090069284A (ko) | 분산 염료, 이의 제조 및 이의 용도 | |
TWI428399B (zh) | 藍色蒽醌染料、彼之製法及用途 | |
TWI707002B (zh) | 分散偶氮染料、其製備方法及其用途 | |
KR102558062B1 (ko) | 착색제 혼합물 | |
MX2008015961A (es) | Colorantes dispersos, su preparacion y uso. | |
CN114929809B (zh) | 分散偶氮染料、其制备方法及其用途 |