CN101287802A - 偶氮颜料制剂 - Google Patents
偶氮颜料制剂 Download PDFInfo
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- CN101287802A CN101287802A CNA2006800383619A CN200680038361A CN101287802A CN 101287802 A CN101287802 A CN 101287802A CN A2006800383619 A CNA2006800383619 A CN A2006800383619A CN 200680038361 A CN200680038361 A CN 200680038361A CN 101287802 A CN101287802 A CN 101287802A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 76
- 239000000049 pigment Substances 0.000 title claims abstract description 74
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims abstract description 16
- -1 aliphatic primary amine Chemical class 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 3
- 239000001052 yellow pigment Substances 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 150000008431 aliphatic amides Chemical class 0.000 claims description 2
- 238000006149 azo coupling reaction Methods 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- 229920000151 polyglycol Polymers 0.000 claims description 2
- 239000010695 polyglycol Substances 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000007646 gravure printing Methods 0.000 abstract description 11
- 230000003287 optical effect Effects 0.000 abstract description 7
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000976 ink Substances 0.000 abstract 2
- 239000002932 luster Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000005859 coupling reaction Methods 0.000 description 14
- 230000008878 coupling Effects 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 10
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 235000014121 butter Nutrition 0.000 description 7
- 235000019197 fats Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000003944 tolyl group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- DLYLVPHSKJVGLG-UHFFFAOYSA-N 4-(cyclohexylmethyl)cyclohexane-1,1-diamine Chemical compound C1CC(N)(N)CCC1CC1CCCCC1 DLYLVPHSKJVGLG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
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- 238000007639 printing Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 1
- MWOOEGJXTBLJOV-UHFFFAOYSA-N 3-oxobutanoyl(phenyl)sulfamic acid Chemical compound S(=O)(=O)(O)N(C1=CC=CC=C1)C(CC(=O)C)=O MWOOEGJXTBLJOV-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/001—Special methods of performing the coupling reaction characterised by the coupling medium
-
- 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
- C09B41/00—Special methods of performing the coupling reaction
-
- 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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/002—Influencing the physical properties by treatment with an amine
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
- C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular compounds
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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
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
本发明涉及偶氮颜料制剂，其特征在于含有4，4′－二氨基二环己基甲烷，其中基于4，4′－二氨基二环己基甲烷的总量，反式，反式异构体的比例为至少25％。根据本发明的偶氮颜料制剂尤其适合于制备在插图凹版印刷方面具有改进的光学密度、较高的光泽和非透印性的凹版印刷油墨。
Description
技术领域
本发明涉及胺配制的偶氮颜料领域，该偶氮颜料尤其用于印刷油墨，例如用于插图(Illustration)凹版印刷中的印刷油墨中。
背景技术
EP 0057880 A1公开了强着色、易流动且易分散的偶氮颜料制剂当在偶合期间或之后添加长链脂族伯胺和式H2N-A-NH2的二胺时获得，其中A是含6-30个碳原子的脂族烃基。4，4′-二氨基二环己基甲烷已知是式H2N-A-NH2的二胺的实例。该化合物是可商购的并通常作为三种立体异构体的混合物形式存在，即顺式，顺式异构体、顺式，反式异构体和反式，反式异构体的混合物，其中据发现该反式，反式异构体比例低于20％：
DE 4334790A1和US 3,347,917公开了可获得具有高含量的反式，反式异构体的4，4′-二氨基二环己基甲烷的方法。一种已知的方法包括例如使4，4′-二氨基二环己基甲烷的异构体混合物首先在甲苯中与两当量苯甲醛起反应以形成相应的4，4′-二(苄叉基氨基)二环己基甲烷。然后通过在二甲氧基乙烷作为溶剂中的碱催化将全部异构体混合物异构化成热力学最稳定的反式，反式二胺。席夫碱的水解产生异构体纯的反式，反式-4，4′-二氨基二环己基甲烷。具有高反式，反式比例的4，4′-二氨基二环己基甲烷对于大工业规模制造具有改进的材料性能，例如温度稳定性和耐溶剂性的聚氨酯弹性体很重要(DE 4334790A 1)。
发明内容
本发明的目的是提供尤其用于凹版印刷油墨中的偶氮颜料制剂，其突出之处在于在插图凹版印刷中的改进的光学密度、较高的光泽和非透印。
已经发现，上述目的令人惊奇地通过一种偶氮颜料制剂达到，该偶氮颜料制剂包含具有提高的反式，反式异构体比例的4，4′-二氨基二环己基甲烷。
本发明因此提供包含4，4′-二氨基二环己基甲烷的偶氮颜料制剂，其中基于4，4′-二氨基二环己基甲烷的总量，反式，反式异构体的比例为至少25％。
纯反式，反式异构体的制备在技术上是复杂的。纯反式，反式异构体的使用虽然是可能的，但对于本发明的目的是根本不必要的。基于4，4’-二氨基二环己基甲烷的总量，将反式，反式异构体的比例限制到25％-75％，尤其是35％-60％从经济和技术的原因考虑是足够的。
已经发现，不依赖于所使用的4，4′-二氨基二环己基甲烷的总量，异构体混合物中的顺式，顺式和顺式，反式异构体的比例总计不应该高于75％。由于非平面立体异构体引起的偶氮颜料的晶格破坏可能导致色彩性能的劣化。
所使用的4，4′-二氨基二环己基甲烷，即一般地，具有根据本发明的反式，反式比例的立体异构体混合物的量基于偶氮颜料的重量有利地为2wt％-30wt％，优选为5wt％-20wt％。
有用的偶氮颜料包括所有用于印刷油墨中的产品，优选二芳基黄色颜料，尤其是乙酰乙酰基芳基酰胺系列的二芳基黄色颜料。尤其优选C.I.颜料黄12、13、14、17、55、63、81、83、87、90、106、113、114、121、124、126、127、136、152、170、171、172、174、176和188，此外还有C.I.颜料红53:1。C.I.颜料黄12是非常特别优选的。
本发明的偶氮颜料制剂优选进一步包含含6-30个碳原子的长链脂族伯胺，例如椰油脂肪胺，油基胺，硬脂基胺，牛油脂肪胺，烷基亚烷基二胺例如牛油脂肪亚丙基二胺，或牛油脂肪二亚丙基三胺。以偶氮颜料制剂的总重量计，含6-30个碳原子的长链脂族伯胺的含量优选为1wt％-30wt％，尤其是5wt％-20wt％。还可以使用所提及的胺的盐，例如乙酸盐代替所提及的胺。
长链脂族伯胺与4，4′-二氨基二环己基甲烷的用量比例可以在一定的限度内变化并且取决于特定颜料的目标性能。最佳关系可容易地通过简单的初步试验测定。
以偶氮颜料制剂的总重量计，添加1wt％-25wt％，尤其是2wt％-20wt％选自脂肪醇聚二醇醚、烷基酚聚二醇醚、脂肪胺和脂肪胺N-氧化物的季铵盐、或它们的组合的添加剂可能是进一步有利的。实例包括硬脂基三甲基氯化铵、十六烷基三甲基氯化铵、椰油烷基三甲基氯化铵、椰油烷基二甲基苄基氯化铵、十二烷基苄基二甲基氯化铵、二椰油烷基二甲基氯化铵、二硬脂基二甲基氯化铵、二牛油脂肪烷基二甲基氯化铵和椰油烷基二甲基氧化胺。
除所提及的组分之外，本发明的颜料制剂还可以包含其它常用的助剂或添加剂，例如表面活性剂、非颜料性和颜料性分散剂、填料、标准化剂、树脂、蜡、消泡剂、防尘剂、增量剂、抗静电剂、配色着色剂、防腐剂、干燥延迟剂、流变性控制添加剂、湿润剂、抗氧化剂、UV吸收剂、光稳定剂、杀生物剂、或它们的组合，以该颜料制剂的总重量计，以0.1wt％-25wt％，尤其是0.5wt％-15wt％的量包含这些试剂。
本发明进一步提供偶氮颜料制剂的制备方法，该方法包括在偶氮偶合之前、期间或之后，但是仍在偶氮颜料的分离之前添加具有反式，反式比例至少25％的4，4′-二氨基二环己基甲烷。例如，它在偶合组分的沉淀中用作沉淀助剂，在偶合之后添加到偶合液中，或配制到滤饼中。它进一步可以在随后的整理操作中添加。上述长链脂族伯胺以及添加剂可以与4，4′-二氨基二环己基甲烷一起地或与之分开地添加。
按常规方法进一步将颜料悬浮液后处理，如通过过滤、洗涤、干燥和研磨进行。获得易分散的偶氮颜料制剂，该制剂提供非常强着色、易流动的印刷油墨，尤其是甲苯基凹版印刷油墨，借此获得有光泽的且非透印的印刷品。
本发明的颜料制剂可以用于将天然或合成来源的高分子量有机材料着色，例如将塑料、树脂、涂料、油漆、电子照相调色剂和显影剂、驻极体材料、滤色器着色，以及将液体油墨(Tinten)、印刷油墨和种子着色。然而，尤其优选它们在制造印刷油墨，尤其是甲苯基凹版印刷油墨中的应用。
本发明还提供包含本发明偶氮颜料制剂的印刷油墨，尤其是凹版印刷油墨。
具体实施方式
实施例
富集反式，反式-4，4′-二氨基二环己基甲烷的制备
根据DE 4334790A1的实施例1-3制备足够量的具有大约75％反式，反式比例(由1H-NMR光谱测定)的4，4′-二氨基二环己基甲烷，它通过混合到可商购的4，4′-二氨基二环己基甲烷(小于20％反式，反式异构体)中得到包含40％反式，反式-或25％反式，反式-异构体的产物，它用于随后的实施例中。
实施例1：P.Y.12
在245g冰-水混合物和106g 31％盐酸中搅拌38g 3，3′-二氯联苯胺(DCB)以形成均匀悬浮液，并在0-15℃下经由57g 38％亚硝酸钠溶液的连续加料进行双重氮化。在该重氮化结束时通过添加大约0.5g氨基磺酸将过量的亚硝酸盐破坏。
将53.2g乙酰乙酰替苯胺引入684g水和57.5g 50％的氢氧化钠溶液中。在小心地搅拌后获得透明溶液，将它冷却至0-5℃。添加2g油基胺乙酸盐并随后通过添加25.4g 80％的乙酸将偶合组分沉淀出。
通过在60min内以连续速率向沉淀的偶合组分中向表面下计量加入DCB双偶氮溶液进行偶合反应。在该反应结束之后，将温度提升到40℃并向其中添加2.5g十二烷基苄基二甲氯化铵、10g牛油脂肪烷基亚丙基二胺以及4.8g具有40％反式，反式含量的4，4′-二氨基二环己基甲烷。将该反应混合物加热到90-100℃并维持该温度30mi n。通过添加大约49.5g 50％的氢氧化钠溶液调节为碱性并在90-100℃下维持该温度另外2h。随后过滤、洗涤、干燥和研磨产物。
根据实施例1制备的颜料制剂具有好的可分散性并且突出之处在于可由其制备产生具有高光学密度的高光泽且非透印性印刷品的甲苯基凹版印刷油墨。
实施例2
根据实施例1制备偶氮颜料制剂，不同之处在于使用具有25％反式，反式含量的4，4′-二氨基二环己基甲烷。
与实施例1相比，根据实施例2制备的颜料制剂提供具有稍微增加的粘度的凹版印刷油墨和具有良好光泽和类似光学密度的印刷品。
对比例
根据实施例1制备偶氮颜料制剂，不同之处在于使用具有大约20％反式，反式含量的4，4′-二氨基二环己基甲烷。
与实施例1相比较，根据对比例制备的颜料制剂提供具有明显增加的粘度的凹版印刷油墨和由其制备的具有更低光泽、更低着色强度和明显更低光学密度的印刷品。
实施例3
根据实施例1制备偶氮颜料制剂，不同之处在于使用7.4g4，4′-二氨基二环己基甲烷。与实施例1相比较，根据实施例3制备的颜料制剂提供具有更红色调的凹版印刷油墨；由其制备的印刷品的突出之处在于改进的光泽和更高的光学密度，尤其是在大的阱深(
)下。
实施例4
根据实施例1制备偶氮颜料制剂，不同之处在于在偶合步骤之前添加4，4′-二氨基二环己基甲烷。获得了具有类似性能的产物。
实施例5
根据实施例1制备偶氮颜料制剂，不同之处在于在过滤之后将4，4′-二氨基二环己基甲烷添加到滤饼中。随后将该滤饼均化，干燥和研磨。获得了具有类似性能的产物。
实施例6：P.Y.126
根据实施例1制备偶氮颜料制剂，不同之处在于用7g乙酰乙酰替-对-茴香胺替换6g所用的乙酰乙酰替苯胺。获得了泛红色的产物。
实施例7：
根据实施例1制备偶氮颜料制剂，不同之处在于用4.7g对乙酰乙酰基氨基苯磺酸的钾盐替换2.8g乙酰乙酰替苯胺。
获得了产生与实施例1相比较更泛绿色的凹版印刷油墨的颜料制剂，由其制备的印刷品的突出之处在于增加的透明性。
实施例8：P.Y.114
根据实施例1制备偶氮颜料制剂，不同之处在于用6.5g乙酰乙酰替对甲苯胺替换6g所使用的乙酰乙酰替苯胺。获得了泛红色的产物，由其制备的甲苯基凹版印刷油墨提供具有改进的光学密度的印刷品。
实施例9
根据实施例1制备偶氮颜料制剂，不同之处在于用牛油脂肪二亚丙基三胺替换所使用的牛油脂肪亚丙基二胺。获得了与由实施例1得到的那种具有类似良好性能的更泛绿色的颜料制剂。
实施例10
根据实施例9制备偶氮颜料制剂，不同之处在于在偶合步骤之前添加牛油脂肪二亚丙基三胺。获得了具有类似良好性能的颜料制剂。实施例11：P.O.13+P.Y.12的混合物
将5.3g 1-苯基-3-甲基-5-吡唑啉酮(PMP)悬浮在100g水和2.8g 50％氢氧化钠溶液中并搅拌直至获得透明溶液。然后通过缓慢添加2.8g80％的乙酸使该PMP沉淀出。在一个单独的容器中，在616g水和51.8g 50％氢氧化钠溶液中搅拌47.9g乙酰乙酰替苯胺以形成透明溶液。将它冷却到0-5℃，向其中添加2g油基胺乙酸盐并通过添加25.4g80％的乙酸使该乙酰乙酰替苯胺沉淀出。通过添加这样多的根据实施例1制备的DCB双偶氮溶液进行偶合反应，直至可检测到轻微的重氮过量。在第二偶合步骤中，将沉淀的乙酰乙酰替苯胺添加到反应混合物中并借助余下的DCB双偶氮溶液结束该偶合反应。颜料的进一步配制按实施例1所指示进行。与实施例1相比较，获得了更泛红色的颜料制剂并且由其制备的印刷油墨的粘度更低且在印刷品中着色更强。
实施例12
将5.3gPMP和47.9g乙酰乙酰替苯胺悬浮在716g水和54.6g 50％氢氧化钠溶液中并搅拌该悬浮液直至获得透明溶液。将它冷却至0-5℃，向其中添加2g油基胺乙酸盐并通过添加28.2g 80％的乙酸使偶合组分沉淀出。在90min内通过添加根据实施例1制备的DCB双偶氮溶液进行偶合反应。颜料的进一步配制按实施例1所指示进行。与实施例1相比较，获得了更泛红色的颜料制剂；由其制备的印刷油墨的粘度更低且在印刷品中着色更强。
Claims (14)
1.偶氮颜料制剂，其特征在于包含4，4′-二氨基二环己基甲烷，其中基于4，4′-二氨基二环己基甲烷的总量，反式，反式异构体的比例为至少25％。
2.根据权利要求1的偶氮颜料制剂，其特征在于基于4，4′-二氨基二环己基甲烷的总量，所述反式，反式异构体的比例为25％-75％。
3.根据权利要求1或2的偶氮颜料制剂，其特征在于基于4，4′-二氨基二环己基甲烷的总量，所述反式，反式异构体的比例为35％-60％。
4.根据权利要求1-3中至少一项的偶氮颜料制剂，其特征在于基于该偶氮颜料的重量，4，4′-二氨基二环己基甲烷含量为2wt％-30wt％。
5.根据权利要求1-4中至少一项的偶氮颜料制剂，其特征在于基于该偶氮颜料的重量，4，4′-二氨基二环己基甲烷含量为5wt％-20wt％。
6.根据权利要求1-4中至少一项的偶氮颜料制剂，其特征在于包含具有6-30个碳原子的长链脂族伯胺。
7.根据权利要求6的偶氮颜料制剂，其特征在于基于该偶氮颜料制剂的总重量，包含1wt％-30wt％的具有6-30个碳原子的长链脂族伯胺。
8.根据权利要求1-7中至少一项的偶氮颜料制剂，其特征在于该偶氮颜料是二芳基黄色颜料。
9.根据权利要求1-8中至少一项的偶氮颜料制剂，其特征在于该偶氮颜料是C.I.颜料黄12、13、14、17、55、63、81、83、87、90、106、113、114、121、124、126、127、136、152、170、171、172、174、176、188或C.I.颜料红53:1。
10.根据权利要求1-9中至少一项的偶氮颜料制剂，其特征在于基于该偶氮颜料制剂的总重量计，包含1wt％-25wt％选自脂肪醇聚二醇醚、烷基酚聚二醇醚、脂肪胺和脂肪胺N-氧化物的季铵盐、或它们的组合。
11.制备根据权利要求1-10中至少一项的偶氮颜料制剂的方法，该方法包括：在偶氮偶合之前、期间或之后，但是仍在偶氮颜料的分离之前，添加具有反式，反式比例至少25％的4，4′-二氨基二环己基甲烷。
12.根据权利要求1-10中至少一项的偶氮颜料制剂用于将天然或合成来源的高分子量有机材料着色的用途。
13.根据权利要求12的用途，用于制备印刷油墨。
14.印刷油墨，其包含根据权利要求1-10中至少一项的偶氮颜料制剂。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005061066.8 | 2005-12-21 | ||
| DE102005061066A DE102005061066A1 (de) | 2005-12-21 | 2005-12-21 | Azopigmentpräparation |
| PCT/EP2006/010980 WO2007079813A1 (de) | 2005-12-21 | 2006-11-16 | Azopigmentpräparation |
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| CN101287802A true CN101287802A (zh) | 2008-10-15 |
| CN101287802B CN101287802B (zh) | 2010-05-19 |
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| Country | Link |
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| US (1) | US7645336B2 (zh) |
| EP (1) | EP1966323B1 (zh) |
| JP (1) | JP5317700B2 (zh) |
| KR (1) | KR20080078676A (zh) |
| CN (1) | CN101287802B (zh) |
| CA (1) | CA2627767A1 (zh) |
| DE (2) | DE102005061066A1 (zh) |
| DK (1) | DK1966323T3 (zh) |
| ES (1) | ES2329617T3 (zh) |
| WO (1) | WO2007079813A1 (zh) |
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| CN106118123A (zh) * | 2016-06-28 | 2016-11-16 | 山东宇虹新颜料股份有限公司 | 一种c.i.颜料橙13的制备方法 |
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| CN106349735B (zh) * | 2016-08-30 | 2017-09-05 | 上虞市东海化工有限公司 | 一种黄色颜料的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA859191A (en) * | 1970-12-22 | E. Beswick Geoffrey | Process for the manufacture of dicarboxylic acid salts of 4,4'-diaminodicyclohexylmethane of enriched trans-trans content | |
| US3347917A (en) | 1961-12-29 | 1967-10-17 | Du Pont | Process for the preparation of di (paraaminocyclohexyl) methane |
| GB1217500A (en) * | 1967-05-24 | 1970-12-31 | Ici Ltd | Separation of trans-trans enriched salts of 4,4'-diaminodicyclohexylmethane |
| CH517821A (de) | 1968-04-17 | 1972-01-15 | Bayer Ag | Verfahren zur Herstellung einer Pigmentzubereitung |
| DE3104257A1 (de) * | 1981-02-07 | 1983-02-03 | Hoechst Ag, 6000 Frankfurt | Azopigmentpraeparationen, verfahren zu ihrer herstellung und ihre verwendung |
| DE3113882A1 (de) * | 1981-04-07 | 1982-10-21 | Hoechst Ag, 6000 Frankfurt | Azopigmentpraeparationen, verfahren zu ihrer herstellung und ihre verwendung |
| US5196594A (en) * | 1988-01-14 | 1993-03-23 | Miles, Inc. | Process for the production of 4,4'-diamino-dicyclohexylmethane with a low trans-trans isomer content by the catalytic hydrogenation of 4,4'-diamino-diphenylmethane |
| EP0567918A3 (en) * | 1992-04-25 | 1993-12-08 | Hoechst Ag | Azopigment preparation |
| JP3259923B2 (ja) * | 1992-11-17 | 2002-02-25 | 株式会社サクラクレパス | ボールペン用油性インキ組成物 |
| DE4334790A1 (de) | 1993-10-13 | 1995-04-20 | Bayer Ag | Verfahren zur Herstellung von trans-trans-4,4'-Diaminodicyclohexylmethan |
| DE19959288C2 (de) * | 1999-12-09 | 2002-01-24 | Clariant Gmbh | Sicherheitstechnisch verbesserte Pigmentzubereitungen |
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2005
- 2005-12-21 DE DE102005061066A patent/DE102005061066A1/de not_active Withdrawn
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2006
- 2006-11-16 CN CN2006800383619A patent/CN101287802B/zh not_active Expired - Fee Related
- 2006-11-16 KR KR1020087014797A patent/KR20080078676A/ko not_active Application Discontinuation
- 2006-11-16 DE DE502006004558T patent/DE502006004558D1/de active Active
- 2006-11-16 EP EP06818571A patent/EP1966323B1/de not_active Not-in-force
- 2006-11-16 ES ES06818571T patent/ES2329617T3/es active Active
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| CN106118123A (zh) * | 2016-06-28 | 2016-11-16 | 山东宇虹新颜料股份有限公司 | 一种c.i.颜料橙13的制备方法 |
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| Publication number | Publication date |
|---|---|
| DE502006004558D1 (de) | 2009-09-24 |
| US20090025600A1 (en) | 2009-01-29 |
| JP5317700B2 (ja) | 2013-10-16 |
| KR20080078676A (ko) | 2008-08-27 |
| EP1966323B1 (de) | 2009-08-12 |
| WO2007079813A1 (de) | 2007-07-19 |
| CN101287802B (zh) | 2010-05-19 |
| ES2329617T3 (es) | 2009-11-27 |
| DE102005061066A1 (de) | 2007-06-28 |
| DK1966323T3 (da) | 2009-12-14 |
| EP1966323A1 (de) | 2008-09-10 |
| US7645336B2 (en) | 2010-01-12 |
| JP2009520840A (ja) | 2009-05-28 |
| CA2627767A1 (en) | 2007-07-19 |
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