CN101679766A - 基于二嗪的颜料制剂 - Google Patents
基于二嗪的颜料制剂 Download PDFInfo
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- CN101679766A CN101679766A CN200880018558A CN200880018558A CN101679766A CN 101679766 A CN101679766 A CN 101679766A CN 200880018558 A CN200880018558 A CN 200880018558A CN 200880018558 A CN200880018558 A CN 200880018558A CN 101679766 A CN101679766 A CN 101679766A
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- 239000000049 pigment Substances 0.000 title claims abstract description 79
- 238000002360 preparation method Methods 0.000 title claims abstract description 42
- 150000005125 dioxazines Chemical class 0.000 title 1
- 239000002270 dispersing agent Substances 0.000 claims abstract description 17
- 239000011347 resin Substances 0.000 claims abstract description 8
- 229920005989 resin Polymers 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- -1 dioxazine compound Chemical class 0.000 claims abstract description 7
- MHVJRKBZMUDEEV-UHFFFAOYSA-N (-)-ent-pimara-8(14),15-dien-19-oic acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(C=C)(C)C=C1CC2 MHVJRKBZMUDEEV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- MHVJRKBZMUDEEV-APQLOABGSA-N (+)-Pimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@](C=C)(C)C=C2CC1 MHVJRKBZMUDEEV-APQLOABGSA-N 0.000 claims abstract description 3
- QUUCYKKMFLJLFS-UHFFFAOYSA-N Dehydroabietan Natural products CC1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 QUUCYKKMFLJLFS-UHFFFAOYSA-N 0.000 claims abstract description 3
- NFWKVWVWBFBAOV-UHFFFAOYSA-N Dehydroabietic acid Natural products OC(=O)C1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 NFWKVWVWBFBAOV-UHFFFAOYSA-N 0.000 claims abstract description 3
- MXYATHGRPJZBNA-KRFUXDQASA-N Isopimaric acid Natural products [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@](C=C)(C)CC2=CC1 MXYATHGRPJZBNA-KRFUXDQASA-N 0.000 claims abstract description 3
- RWWVEQKPFPXLGL-ONCXSQPRSA-N L-Pimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC=C(C(C)C)C=C2CC1 RWWVEQKPFPXLGL-ONCXSQPRSA-N 0.000 claims abstract description 3
- RWWVEQKPFPXLGL-UHFFFAOYSA-N Levopimaric acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CC=C(C(C)C)C=C1CC2 RWWVEQKPFPXLGL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- NFWKVWVWBFBAOV-MISYRCLQSA-N dehydroabietic acid Chemical compound OC(=O)[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 NFWKVWVWBFBAOV-MISYRCLQSA-N 0.000 claims abstract description 3
- 229940118781 dehydroabietic acid Drugs 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- MHVJRKBZMUDEEV-KRFUXDQASA-N sandaracopimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@](C=C)(C)C=C2CC1 MHVJRKBZMUDEEV-KRFUXDQASA-N 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 14
- 239000011342 resin composition Substances 0.000 claims description 10
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 230000011218 segmentation Effects 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 2
- 229920002521 macromolecule Polymers 0.000 claims description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract description 2
- YPGLTKHJEQHKSS-ASZLNGMRSA-N (1r,4ar,4bs,7r,8as,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@H](C(C)C)C[C@@H]2CC1 YPGLTKHJEQHKSS-ASZLNGMRSA-N 0.000 abstract 1
- UZZYXZWSOWQPIS-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)benzaldehyde Chemical compound FC1=CC(C=O)=CC(C(F)(F)F)=C1 UZZYXZWSOWQPIS-UHFFFAOYSA-N 0.000 abstract 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 abstract 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000000227 grinding Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000012752 auxiliary agent Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 3
- 238000006253 efflorescence Methods 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 206010037844 rash Diseases 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000004595 color masterbatch Substances 0.000 description 2
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000009837 dry grinding Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000000275 quality assurance Methods 0.000 description 2
- 238000001238 wet grinding Methods 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 239000010431 corundum Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 150000001457 metallic cations Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- 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
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
- C08K5/357—Six-membered rings
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- 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
- C09B67/0002—Grinding; Milling with solid grinding or milling assistants
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- 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
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
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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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
- C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
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- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
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- Polymers & Plastics (AREA)
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- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
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Abstract
本发明涉及颜料制剂，其特征为含有a)式(I)的二噁嗪化合物作为基础颜料；和b)通式(II)的二噁嗪化合物作为颜料分散剂，Q－[Y－X]m(II)，其中Q代表式(I)的基础颜料的m价残基，Y代表－(CR1R2)x－，其中x为1至6，其中R1和R2彼此独立地代表氢或C1至C4烷基，X代表咪唑残基，该残基通过碳原子连接于Y桥联元，m为1至4的数值；和c)树脂组分，其选自松香酸、脱氢松香酸、二氢松香酸、四氢松香酸、左旋海松酸、右旋海松酸、异右旋海松酸、松香树脂、部分氢化的松香树脂、上述酸的树脂皂及其混合物。
Description
背景技术
颜料制剂是基础颜料和助剂的组合。在此，所述助剂可分为两类：所谓的颜料分散剂类，其是用特定活性的基团取代的颜料，和非颜料性助剂类。将助剂添加到颜料中，以便于在应用介质中分散，特别是在涂料、印刷油墨和墨水(Tinten)中分散，和改进所述颜料的流变学和色彩性能。
在印刷油墨的制备中，第一步中由所述颜料制备具有高颜料含量(Pigmentierung)(＞15％)的浓色母料。然后将这些浓色母料调节为印刷油墨浓度(6-10％)以制备印刷油墨。在EP-A-0321919和EP-A-0504923中描述的二噁嗪着色剂在浓缩物中显示不完全令人满意的粘度和储存稳定性。这导致在印刷油墨制备和在浓色母料的储存方面的问题。另外，需要大量的溶剂或溶解和粘结介质以调节对于印刷操作所需要的印刷粘度。这导致减小的印刷油墨着色强度。
发明内容
本发明的目的是提供具有紫色色调的用于印刷墨水的着色剂，其克服了上述缺陷。
这一目的令人惊奇地通过如下颜料制剂实现，所述颜料制剂是由P.V.23、树脂酸或树脂酸衍生物和基于二噁嗪化合物的特定颜料分散剂的组合构成的。
本发明提供如下颜料制剂，其特征在于包含
a)作为基础颜料的式(I)的二噁嗪化合物
和
b)作为颜料分散剂的通式(II)的二噁嗪化合物，
Q-[Y-X]m (II)
其中
Q代表式(I)的基础颜料的m价残基，
Y代表-(CR1R2)x-，其中x为1至6，其中R1和R2彼此独立地代表氢或C1-C4烷基，
X代表咪唑残基，该残基通过碳原子连接于桥联元Y，
m代表1至4的数值；
和
c)树脂组分，其选自松香酸、脱氢松香酸、二氢松香酸、四氢松香酸、左旋海松酸、右旋海松酸、异右旋海松酸、松香树脂以及部分氢化的松香树脂、所述酸的树脂皂及其混合物。
优选如下的式(II)的颜料分散剂，其中
Y代表亚甲基、亚乙基或亚丙基，
X代表咪唑基，其通过5位连接于桥联元Y，和
m代表1至2.5的数。
为了本发明的目的，非常特别优选式(III)的颜料分散剂
其中
Q如上所定义，和
M代表1至2.5的数值，特别是1至2。
优选的树脂组分是可商购的松香类以及所述酸的盐，也被称为树脂皂，其中阳离子是金属阳离子，优选选自碱金属、碱土金属、土金属和过渡金属，例如Cr、Mn、Fe、Co、Ni、Cu、Zn、Ag。特别优选Li、Na、K、Mg、Ca、Sr，特别是Na和K。
优选的颜料制剂包含
a)50-99.7wt％，更优选80-99.7wt％和最优选90-99.2wt％的式I的基础颜料，
b)0.1-30wt％，更优选0.1-10wt％和最优选0.1-5wt％的式II或III的颜料分散剂，
c)0.1-30wt％，更优选0.1-10wt％和最优选0.1-5wt％的树脂组分，
每种情况下基于所述颜料制剂的总重量计。
本发明的颜料制剂除了所述的组分还可以含有另外的常规助剂或添加剂，例如表面活性剂、分散剂、填料、标准化剂、不同于上述那些树脂的树脂、蜡、消泡剂、防尘剂、增量剂、抗静电剂、防腐剂、干燥抑制剂、润湿剂、抗氧化剂、UV吸收剂和光稳定剂，优选其量为基于所述颜料制剂的总重量计的0.1-10wt％，特别是0.5-5wt％。可用的表面活性剂包括阴离子型的或阴离子活性的、阳离子型的或阳离子活性的和非离子型的或两性的物质，或这些试剂的混合物。
本发明还提供制备根据本发明的颜料制剂的方法，其特征在于在细分操作，例如捏合、湿法研磨或干法研磨操作之前或期间，或者在整理处理之前即刻或期间，将C.I.颜料紫23与式(II)的颜料分散剂和所述树脂组分掺混。
例如，可以将干燥的组分以颗粒或粉末形式在研磨之前或之后进行混合；可以将所述一个组分添加到湿或干燥形式的其它组分中，例如通过将湿滤饼形式的各组分混合。
混合可以例如通过如下方式完成：在干燥形式下、在湿形式下研磨，例如通过捏合，或者在悬浮液中，或者通过这些方法的组合。研磨可以在水、溶剂、酸或研磨助剂例如盐的添加下进行。导致所述颜料晶体的细分的捏合操作特别是在有机溶剂的存在下的盐捏合操作。
特别优选在湿法研磨期间，或者在整理处理中，将所述颜料分散剂和所述树脂组分添加到式I的基础颜料中。例如，所述整理处理可以在水和/或溶剂中进行，并且通常在升高的温度下，例如最高至200℃，和任选地在升高的压力下进行。不言而喻的是，所述颜料分散剂和所述树脂组分还可以在不同的时间分份添加。
已知的干燥设备组可以用于干燥湿的颜料制剂，例如干燥箱、叶轮式干燥器、滚筒式干燥器、接触式干燥器和特别是旋转闪蒸干燥器和喷雾干燥器。
本发明还提供可通过如上所述方法获得的颜料制剂。
本发明的颜料制剂可用于将天然或合成来源的高分子有机材料，例如塑料、树脂、涂料、油漆、电子照相调色剂和显色剂、滤色片以及墨水，还有喷墨墨水着色，和特别用于印刷油墨。
令人惊奇地表明，包含本发明颜料制剂的印刷油墨浓缩物，与如在EP-A-0321919和EP-A-0504923中描述的颜料制剂相比具有明显更好的流变性，并且在储存中不变稠。
特别地，本发明的颜料制剂显示出优异的流变性能，即使在所述印刷油墨浓缩物的高的颜料含量下(例如22％)。由这些印刷油墨浓缩物制备的基于醇和酯的印刷油墨得到具有高透明性和高光泽的印刷品。
此外，本发明的颜料制剂具有甚至在各种其它印刷体系中的宽相容性。
本发明还提供特征为包含15-25wt％，优选17-24wt％，特别是18-22wt％的本发明颜料制剂的印刷油墨浓缩物。
具体实施方式
在下述实施例中，百分比数据是指重量百分比，重量份，除非另外说明。
实施例1：
a)通过干法研磨的细分操作
将30g根据BIOS Final Report 960，第75页制备的粗结晶的粗制颜料(颜料紫23)引入到圆筒形的1升塑料容器中，所述容器填充有1400g直径为12mm的刚玉研磨介质。然后将该混合物在振动磨机上振摇的条件下精细研磨4小时。之后将研磨料从所述研磨介质中筛分出。获得29g研磨料。
b)整理
向450g水和336g得自a)的P.V.23粗制颜料的研磨料中添加112g由部分氢化的松香树脂在氢氧化钠溶液中形成的5％浓度溶液和250g异丁醇(85％浓度)。在150℃下在高压釜中搅拌数小时后，添加330份3.8％浓度的其中m为1的式(III)的颜料分散剂的水性悬浮液，并将溶剂蒸馏除去。
c)后处理
然后将该批料趁热抽滤。将产物洗涤至无盐并在80℃下真空干燥和随后粉化。
实施例2：
向350g水和336g得自实施例1a)的P.V.23粗制颜料的研磨料中加入224g由部分氢化的松香树脂在氢氧化钠溶液中形成的5％浓度的水溶液和250g异丁醇(85％浓度)。在150℃下在高压釜中搅拌数小时后，将330份3.8％浓度的其中m为1的式(III)的颜料分散剂的水性悬浮液加入，并将溶剂蒸馏除去。
然后将该批料趁热抽滤。将产物洗涤至无盐并在80℃下真空干燥和随后粉化。
由本发明的颜料制剂制备的印刷油墨在NC-版印刷中根据测试规程PV 3/20(Clariant International AG，Global QualityAssurance(全球质量保证)，2005年7月)显示出非常好的粘度、触变性和储存稳定性(表1)：
表1：PV3/20测试结果(流变性)
| 样品 | 具有3mm喷嘴直径的液流杯(45ml体积)[秒] | 在剪切速率D＝200s-1下的粘度*[mPa·s] |
| 实施例1 | 13.9 | 116 |
| 实施例2 | 15.2 | 116 |
*用旋转粘度计测量
实施例3：
将252g二噁嗪粗制颜料颜料紫23与1125g氯化钠(＜30微米)在实验室捏合机中混合，并与230ml DMF一起在50℃下捏合8小时。然后将捏合物料与11000g 5wt％浓度的盐酸掺混，抽滤并用去离子(E-)水洗涤。将滤饼在500ml去离子水中调成糊剂并在60℃下与85g由部分氢化的松香树脂在氢氧化钠溶液中形成的5％浓度水溶液一起和与105g其中m是1的式(III)的颜料分散剂的9％浓度水性悬浮液一起添加。然后将该批料趁热抽滤。将产物洗涤至无盐并在80℃下真空干燥和随后粉化。
Claims (10)
1.一种颜料制剂，其包含
a)作为基础颜料的式(I)的二噁嗪化合物
和
b)作为颜料分散剂的通式(II)的二噁嗪化合物，
Q-[Y-X]m (II)
其中
Q代表式(I)的基础颜料的m价残基，
Y代表-(CR1R2)x-，其中x为1至6，其中R1和R2彼此独立地代表氢或C1-C4烷基，
X代表咪唑残基，该残基通过碳原子连接于桥联元Y，
m代表1至4的数值；
和
c)树脂组分，其选自松香酸、脱氢松香酸、二氢松香酸、四氢松香酸、左旋海松酸、右旋海松酸、异右旋海松酸、松香树脂、部分氢化的松香树脂、所述酸的树脂皂及其混合物。
2.如权利要求1所述的颜料制剂，其中
Y代表亚甲基、亚乙基或亚丙基，
X代表咪唑基，其通过5位连接于桥联元Y，和
m代表1至2.5的数。
3.如权利要求1或2所述的颜料制剂，其中该颜料制剂包含式(III)的颜料分散剂
其中
Q如权利要求1中定义，和
m代表1至2.5的数值。
4.如权利要求1至3中一项或多项所述的颜料制剂，其中该颜料制剂包含
a)50-99.7wt％的式I的基础颜料，
b)0.1-30wt％的式II或III的颜料分散剂，
c)0.1-30wt％的树脂组分，
每种情况下基于所述颜料制剂的总重量计。
5.如权利要求1至4中一项或多项所述的颜料制剂，其中该颜料制剂包含
a)80-99.7wt％的式I的基础颜料，
b)0.1-10wt％的式II或III的颜料分散剂，
c)0.1-10wt％的树脂组分，
每种情况下基于所述颜料制剂的总重量计。
6.制备如权利要求1至5中一项或多项所述的颜料制剂的方法，其中在细分操作之前或期间，或者在整理处理之前即刻或期间，将式(I)的C.I.颜料紫23与式(II)的颜料分散剂和所述树脂组分掺混。
7.如权利要求1至5中一项或多项所述的颜料制剂用于将天然或合成来源的高分子有机材料着色的用途。
8.如权利要求7所述的用途，其中所述材料是塑料、树脂、涂料、油漆、电子照相调色剂和显影剂、滤色片或墨水。
9.如权利要求7或8所述的用途，用于将喷墨墨水和印刷油墨着色。
10.一种印刷油墨浓缩物，其包含15-25wt％的如权利要求1至5中一项或多项所述的颜料制剂。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007031354A DE102007031354A1 (de) | 2007-07-05 | 2007-07-05 | Pigmentzubereitungen auf Basis von Dioxazinen |
| DE102007031354.5 | 2007-07-05 | ||
| PCT/EP2008/004522 WO2009003568A2 (de) | 2007-07-05 | 2008-06-05 | Pigmentzubereitungen auf basis von dioxazinen |
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| Publication Number | Publication Date |
|---|---|
| CN101679766A true CN101679766A (zh) | 2010-03-24 |
| CN101679766B CN101679766B (zh) | 2014-04-09 |
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| CN200880018558.5A Active CN101679766B (zh) | 2007-07-05 | 2008-06-05 | 基于二噁嗪的颜料制剂 |
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| Country | Link |
|---|---|
| US (1) | US8293441B2 (zh) |
| EP (1) | EP2176358B1 (zh) |
| JP (1) | JP5578727B2 (zh) |
| CN (1) | CN101679766B (zh) |
| DE (1) | DE102007031354A1 (zh) |
| ES (1) | ES2389669T3 (zh) |
| WO (1) | WO2009003568A2 (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103408965A (zh) * | 2013-08-08 | 2013-11-27 | 大连理工大学 | 一类含有酰亚胺和三苯二噁嗪结构的染料及其制备方法 |
| CN106133073A (zh) * | 2014-03-31 | 2016-11-16 | 富士胶片株式会社 | 水系喷墨用颜料分散体及其制造方法以及水系喷墨墨水 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TW201105750A (en) * | 2009-03-31 | 2011-02-16 | Solvay | Process for the preparation of easily dispersible violet pigment |
| JP5620115B2 (ja) * | 2010-02-02 | 2014-11-05 | 富士フイルム株式会社 | 顔料微粒子分散体、これを用いた光硬化性組成物及びカラーフィルタ、これに用いられる新規化合物 |
| CN103270119B (zh) | 2010-12-30 | 2016-04-20 | 巴斯夫欧洲公司 | 表面改性的颜料制剂 |
| JP6219333B2 (ja) * | 2015-03-31 | 2017-10-25 | 富士フイルム株式会社 | 顔料分散物及びその製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US595129A (en) * | 1897-12-07 | Signature-register and machine-index | ||
| DE2742575C2 (de) * | 1977-09-22 | 1982-05-19 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Feinverteilung von Pigmenten der Dioxazinreihe |
| FR2515668A1 (fr) * | 1981-11-02 | 1983-05-06 | Sandoz Sa | Nouveaux composes dioxaziniques, leur preparation et leur utilisation comme pigments |
| DE3838814A1 (de) * | 1987-12-22 | 1989-07-06 | Hoechst Ag | Neue pigmente und ihre verwendung |
| JP3388591B2 (ja) * | 1991-03-22 | 2003-03-24 | クラリアント・ゲゼルシヤフト・ミト・ベシユレンクテル・ハフツング | Ｃ．ｉ．ピグメント・バイオレット２３を基礎とする顔料調製物の製造方法 |
| DE4400329A1 (de) * | 1994-01-07 | 1995-07-20 | Hoechst Ag | Verwendung von Fettsäuretauriden zum Dispergieren polycyclischer Pigmente |
| DE19616364A1 (de) * | 1996-04-24 | 1997-10-30 | Hoechst Ag | Oberflächenbehandelte Chinacridon- und Dioxazin-Pigmente |
| DE19709798A1 (de) | 1997-03-10 | 1998-09-17 | Clariant Gmbh | Pigmentzubereitungen und Verfahren zu ihrer Herstellung |
| JPH11302553A (ja) * | 1998-04-24 | 1999-11-02 | Dainippon Ink & Chem Inc | 表面処理顔料の製造方法 |
| GB9911719D0 (en) * | 1999-05-21 | 1999-07-21 | Clariant Int Ltd | Organic compounds |
| DE102004010282A1 (de) * | 2004-03-03 | 2005-09-22 | Clariant Gmbh | Violettes Farbmittel für Color Filter, Ink Jet Tinten, elektrophotographische Toner und Entwickler und e-inks |
| EP1761607B1 (de) * | 2004-06-16 | 2010-10-20 | Colour Ltd. | Verfahren zur herstellung von beta-kupferphthalocyanin-blaupigmenten und deren verwendung |
| DE102005028106A1 (de) * | 2004-06-16 | 2006-01-12 | Colour Ltd. | Verfahren zur Herstellung von organischen Pigmenten und deren Verwendung |
| DE102005024722A1 (de) * | 2005-05-31 | 2006-12-07 | Clariant Produkte (Deutschland) Gmbh | Blaues Farbmittel auf Basis von C.I. Pigment Blue 80 |
-
2007
- 2007-07-05 DE DE102007031354A patent/DE102007031354A1/de not_active Withdrawn
-
2008
- 2008-06-05 JP JP2010513700A patent/JP5578727B2/ja not_active Expired - Fee Related
- 2008-06-05 CN CN200880018558.5A patent/CN101679766B/zh active Active
- 2008-06-05 US US12/667,626 patent/US8293441B2/en active Active
- 2008-06-05 WO PCT/EP2008/004522 patent/WO2009003568A2/de active Application Filing
- 2008-06-05 ES ES08773367T patent/ES2389669T3/es active Active
- 2008-06-05 EP EP08773367A patent/EP2176358B1/de active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103408965A (zh) * | 2013-08-08 | 2013-11-27 | 大连理工大学 | 一类含有酰亚胺和三苯二噁嗪结构的染料及其制备方法 |
| CN106133073A (zh) * | 2014-03-31 | 2016-11-16 | 富士胶片株式会社 | 水系喷墨用颜料分散体及其制造方法以及水系喷墨墨水 |
| CN106133073B (zh) * | 2014-03-31 | 2019-06-18 | 富士胶片株式会社 | 水系喷墨用颜料分散体及其制造方法以及水系喷墨墨水 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5578727B2 (ja) | 2014-08-27 |
| US8293441B2 (en) | 2012-10-23 |
| ES2389669T3 (es) | 2012-10-30 |
| DE102007031354A1 (de) | 2009-01-08 |
| EP2176358A2 (de) | 2010-04-21 |
| JP2010532398A (ja) | 2010-10-07 |
| US20100196816A1 (en) | 2010-08-05 |
| WO2009003568A2 (de) | 2009-01-08 |
| EP2176358B1 (de) | 2012-08-15 |
| WO2009003568A3 (de) | 2009-06-04 |
| CN101679766B (zh) | 2014-04-09 |
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