CN117242139A - 用于无机和有机颜料的通用分散剂 - Google Patents
用于无机和有机颜料的通用分散剂 Download PDFInfo
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- CN117242139A CN117242139A CN202280032189.5A CN202280032189A CN117242139A CN 117242139 A CN117242139 A CN 117242139A CN 202280032189 A CN202280032189 A CN 202280032189A CN 117242139 A CN117242139 A CN 117242139A
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- 235000003441 saturated fatty acids Nutrition 0.000 description 1
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- 239000000243 solution Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- 239000008399 tap water Substances 0.000 description 1
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- 239000004753 textile Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
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- 230000002110 toxicologic effect Effects 0.000 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
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- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
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- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
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- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
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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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/0086—Non common dispersing agents anionic dispersing agents
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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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
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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
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- C09D7/45—Anti-settling agents
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
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- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
- C08F220/286—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
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Abstract
本发明涉及水性颜料制剂,其包含:(A)至少一种有机和/或无机颜料和/或填料,(B)至少一种阴离子分散剂,其含有由含单羧酸/二羧酸的单体和非离子水溶性烯属不饱和单体形成的共聚物;(C)至少一种非离子聚合物分散剂,其包含含有至少一种有机亲颜料基团和至少一个聚乙二醇嵌段的嵌段共聚物和/或接枝共聚物。所述水性颜料制剂适用于将墨、色漆、清漆和建筑涂料着色。
Description
技术领域
本发明涉及水基无机和有机颜料的制剂或分散体、它们的生产方法和它们用于将各种天然和合成材料,尤其是涂料、色漆(Farben)、清漆(Lacken)、釉、木材保护体系和墨着色的用途。
背景技术
无机颜料主要由矿物或金属盐,如铬酸盐、金属氧化物、硫酸盐、硫化物、碳酸盐和氰化物组成。它们由于其耐光牢度和低成本而在工业上广泛应用。相反,有机颜料通常由碳环和碳链组成,并且表现出更明亮、更饱满的颜色和更高的颜色强度。这两种类型的颜料都是固体粒子,但由于它们的性质不同而具有不同的表面化学。为了在上述制剂中使用颜料,必须使用特定的表面活性物质,如润湿助剂和分散助剂,以改变表面化学并使颜料粒子能够有效分散。根据已知的粒子稳定化机理,所用的润湿助剂和分散助剂能够实现被分散的粒子在这些施用介质中的有效的空间和/或静电稳定化,而不使颜料粒子絮凝或再附聚。
需要提供特别在粒度分布、与各自施用介质的相容性和混溶性、色彩性质、颜料含量、流变特性和稳定性方面满足苛刻技术要求的用于上述应用的水性颜料制剂。
例如在毒理学和生态毒理学状况方面也符合监管要求的发泡倾向是该行业面临的日益增长的挑战。
其原因特别在于,化学品立法的逐步收紧和生态标签,例如德国蓝天使或欧盟生态标签的授予导致越来越多常用于颜料制剂的配制剂组分不再能使用,或只能在有限程度上用于某些应用领域。这特别适用于润湿剂和分散剂。例如,由于生物累积和激素降解产物,烷基酚乙氧基化物(APEO)现在受到严格监管并禁止用于许多用途。尽管三苯乙烯基苯酚乙氧基化物(TSPEO)可能继续使用,但由于不利的生态毒理学状况,在行业中仍然存在放弃使用TSPEO的强烈趋势。过去使用的基于酚醛清漆或双酚A的分散剂的使用出于相同原因受到限制。基于伯胺和仲胺的烷氧基化反应产物作为分散剂的使用出于监管和技术原因对于一些应用同样是成问题的,因此仅在有限程度上可行。
现有技术中描述了含有各种声称对有机或无机颜料普遍有效的分散助剂的水性颜料制剂。
US-5340394描述了基于具有200至700的低分子量的聚乙二醇聚醚与非离子烷基糖苷表面活性剂的组合的颜料浓缩物。
WO-2020/152093教导了水性颜料制剂,其包含(A)至少一种有机和/或无机颜料和/或填料,(B)至少一种式(I)或(II)的分散剂,或式(I)和(II)的分散剂的混合物,
其中n是大于或等于1,优选1至5,更优选1至2的整数,z是大于或等于1,优选1至10,更优选1至4的整数,R1是具有1至10个碳原子的脂族直链或支链烃基或是氢原子或是结构单元-O-X或结构单元-CH2-O-X,且结构单元X对应于式(III)。
DE-10 2005 019 384教导了式(I)的聚合物,
其中R1表示:各自彼此独立地为H或具有1至6个碳原子的烷基;R2表示:H、具有1至8个碳原子的烷基、碱金属离子、碱土金属离子、铵离子或任何其它碱的残基;R3表示:具有6至18个碳原子的芳基或芳烷基;R4、R5表示:H或具有1至6个碳原子的烷基;R6、R7:各自独立地表示H或甲基;R8、R9:H或任何端基;a表示:0.1至0.9;b表示:0.9至0.1;c表示:0.001至0.5;m表示:1至4;n表示:1至150。该发明的聚合物尤其适合作为漆中的颜料或填料的分散剂。
DE-930655U1教导了一种用于油漆或类似涂料组合物的水性非堵塞性着色剂,所述着色剂在20℃下具有0.05至1.5Ns/m2(即0.5至15泊,优选1至12泊)的粘度并含有分散存在于分散剂体系中的固体颜料粒子,所述分散剂体系由水和水混溶性非挥发性胶束化分散剂的混合物组成,所述分散剂含有亲水结构部分和能够吸附到颜料表面上的结构部分(其亲水性通常低于疏水性结构部分),其中
a)所述分散剂体系还含有相对少量(基于分散剂体系的重量计小于50重量%,优选小于30重量%)的非挥发性大分子非胶束化辅助材料,其具有230(优选250)至4500的重均分子量并选自
i)与水和非挥发性分散剂的混合物可混溶的液体,和/或
ii)可溶或可分散在所述体系中的具有低于150℃的熔点的粒状有机固体,
b)在颜料的所选重量下,非挥发性胶束化分散剂与颜料的重量比比在仅由相同颜料、水和相同非挥发性胶束化分散剂组成的参比着色剂的丹尼尔流动点处存在的非挥发性胶束化分散剂与颜料的重量比大至少5%(优选15%),
c)着色剂的流动性使得当所述非堵塞性着色剂在25℃下在直径为2mm且长度为15mm的圆柱形孔中在50%的环境相对湿度下储存18小时后,不大于320MN/m2的压力足以使剩余着色剂从孔中流出,和
d)“非挥发性”代表在25℃下低于1.3N/m2(优选低于1.0N/m2)的蒸气压。
EP-1092756教导了一种颜料制剂,其包含颜料和/或炭黑和聚合物和/或选自以下系列的表面活性剂:交联聚氧化亚乙基丙烯酸、脂肪醇聚乙二醇醚、聚乙烯基吡咯烷酮、醇烷氧基化物、木质素磺酸盐、烷基酚聚二醇醚、萘磺酸衍生物或其混合物,其由水性分散体通过冷冻干燥制成。其可用于水基色漆和清漆体系、乳胶漆、印刷油墨、墨水体系和涂料体系中的着色和/或抗静电处理。
WO-2009/145285教导了一种包含着色剂分散体的记录墨,所述着色剂分散体包含:
着色性的试剂和
水,
其中所述分散剂是含有由式(1)至(3)表示的单元的聚羧酸分散剂:
其中R1、R2和R4选自氢原子和CH3;R3选自氢原子和C1-C3烷基;R5是C1-C3烷基;AO和BO是C2-C3氧亚烷基;M选自碱金属、碱土金属、铵和有机胺;m是1至30的整数;且n是5至50的整数,其中所述着色性的试剂是黑色颜料、品红色颜料、青色颜料和黄色颜料的任一种。
US-7659340教导了使用包含至少一种醇酸相容性表面活性剂和至少一种胶乳相容性表面活性剂的表面活性剂混合物的颜料浆。
WO-2014/000842描述了包含脂肪酸缩合产物和非离子表面活性剂作为分散助剂的水性颜料制剂。
US-2018/244925教导了包含基于羧酸酯和/或羧酰胺的水溶性非离子表面活性共聚物和磷表面活性剂或磷酸表面活性剂作为分散助剂的颜料配制剂。
从现有技术中显而易见,只有通过使用水溶性表面活性剂作为颜料配制剂的组分时才能实现通用分散性质。但是,这样的水溶性表面活性剂具有低分子量,可容易迁移至涂层表面,因此如果它们用于水性涂料组合物如水基色漆,则表面活性剂经常容易渗出。在寒冷潮湿气氛中,这样的渗出在干燥中或已干燥的色漆表面上以垂直标记(通常被称为“蜗牛纹”)的形式可见。另一方面,Gabel在European Coatings Journal02-2019,第90-94页中表明,聚合物分散剂的相对较高分子量和化学结构使得它们较不易浸出。这是由于它们在颜料表面上的常见多重粘附点和由于较慢的布朗分子运动以及聚合物链与其它色漆和清漆成分的相互缠结导致的它们在色漆和清漆配制剂内的相对较低活动性导致的。
很明显,尽管存在所述现有技术,但总是仍然需要用于具有改进的效能的颜料配制剂的通用分散助剂。该颜料配制剂应该具有尽可能高的颜色强度。此外,甚至在较长期储存时它们应该保持稳定并且不是触变性的。
发明内容
现在已经令人惊讶地发现,两种聚合物分散剂的组合能够实现无机和/或有机颜料的稳定的通用配制剂,其在上述着色应用中表现出所需性质,尤其是在低配制剂粘度下的易分散性和高颜色强度。此外,已经令人惊讶地发现,两种聚合物分散剂的组合在颜料制剂中表现出由单个组分无法获得的协同效应。
作为第一个主题,本发明涉及一种颜料制剂,其含有
(A)至少一种有机和/或无机颜料和/或填料;
(B)至少一种阴离子共聚物作为分散剂,其含有
(I)40至95摩尔%的阴离子单体的结构单元,所述阴离子单体选自丙烯酸、甲基丙烯酸、衣康酸、2-羧乙基丙烯酸、马来酸、其混合物及其各自的盐,优选甲基丙烯酸或其盐,和
(II)5至60摩尔%的具有式(B1)的重复单元的单体的结构单元
其中
R11、R12和R13互相独立地选自H、甲基和乙基,
R4是H或具有1至4个碳原子的烷基,
X选自O、COO、CONH、CH2O或CH2CH2O,
Y是亚乙基
Z是亚丙基、亚丁基或苯基亚乙基,
m是0至100的整数,
n是1至100的整数,和
m+n大于5,和
(C)至少一种非离子共聚物,其含有至少一种具有芳族基团的结构单元和至少一种具有聚乙二醇基团的结构单元,和
(H)水。
本发明的颜料制剂可任选还含有如下附加成分:
(D)润湿剂,
(E)其他表面活性剂和/或分散剂,
(F)一种或多种有机溶剂和/或一种或多种水溶助长性物质和/或其混合物,和
(G)常规用于生产水性颜料分散体的其他添加剂。
优选的颜料制剂含有5至80重量%,优选10至70重量%,尤其优选30至70重量%的组分(A)。
优选的颜料制剂含有0.1至30重量%,优选1至20重量%,尤其优选2至15重量%的组分(B)。
优选的颜料制剂含有0.1至30重量%,优选1至20重量%,尤其优选2至15重量%的组分(C)。
优选的颜料制剂含有加至100重量%的水。
特别优选的颜料制剂包含如下比例的成分:
(A)5至80重量%,更特别是10至70重量%,
(B)0.1至30重量%,更特别是1至20重量%,
(C)0.1至30重量%,更特别是1至20重量%,
(D)0至10重量%,更特别是0.1至5重量%,
(E)0至20重量%,更特别是1至10重量%,
(F)0至30重量%,更特别是5至20重量%,
(G)0至20重量%,更特别是0.1至5重量%,
在每种情况下基于颜料制剂的总重量(100重量%)计。
在本发明的颜料制剂包含组分(D)、(E)、(F)和(G)中的一种或多种的情况下,其最小浓度互相独立地优选为基于颜料制剂的总重量计至少0.01重量%,更特别是至少0.1%。
组分(A)
本发明的颜料制剂的组分(A)是细分的有机或无机颜料或填料,或不同的有机和/或无机颜料和/或填料的混合物。组分(A)也可以是可溶于特定溶剂并在其他溶剂中着色的染料。颜料既可以以干粉形式使用,也可以作为水湿滤饼使用。
所用有机颜料优选是
单偶氮、双偶氮、色淀偶氮、β-萘酚、萘酚AS、苯并咪唑酮、双偶氮缩合颜料、偶氮金属络合物颜料和多环颜料,如酞菁、喹吖啶酮、苝、芘酮(Perinon)、硫靛、蒽嵌蒽二酮、蒽酮、蒽醌、异蒽酮紫、皮蒽酮、二嗪、喹酞酮、异吲哚啉酮、异吲哚啉和吡咯并吡咯二酮颜料或炭黑;
炭黑颜料,例如气黑或炉黑;
单偶氮和双偶氮颜料,尤其是染料索引(Farbindex)颜料:颜料黄1、颜料黄3、颜料黄12、颜料黄13、颜料黄14、颜料黄16、颜料黄17、颜料黄73、颜料黄74、颜料黄81、颜料黄83、颜料黄87、颜料黄97、颜料黄111、颜料黄126、颜料黄127、颜料黄128、颜料黄155、颜料黄174、颜料黄176、颜料黄191、颜料黄213、颜料黄214、颜料黄219、颜料红38、颜料红144、颜料红214、颜料红242、颜料红262、颜料红266、颜料红269、颜料红274、颜料橙13、颜料橙34或颜料棕41;β-萘酚和萘酚AS颜料,尤其是染料索引颜料:颜料红2、颜料红3、颜料红4、颜料红5、颜料红9、颜料红12、颜料红14、颜料红53:1、颜料红112、颜料红146、颜料红147、颜料红170、颜料红184、颜料红187、颜料红188、颜料红210、颜料红247、颜料红253、颜料红256、颜料橙5、颜料橙38或颜料棕1;色淀偶氮和金属络合物颜料,尤其是染料索引颜料:颜料红48:2、颜料红48:3、颜料红48:4、颜料红57:1、颜料红257、颜料橙68或颜料橙70;苯并咪唑啉颜料,尤其是染料索引颜料:颜料黄120、颜料黄151、颜料黄154、颜料黄175、颜料黄180、颜料黄181、颜料黄194、颜料红175、颜料红176、颜料红185、颜料红208、颜料紫32、颜料橙36、颜料橙62、颜料橙72或颜料棕25;异吲哚啉酮和异吲哚啉颜料,尤其是染料索引颜料:颜料黄139或颜料黄173;酞菁颜料,尤其是染料索引颜料:颜料蓝15、颜料蓝15:1、颜料蓝15:2、颜料蓝15:3、颜料蓝15:4、颜料蓝15:6、颜料蓝16、颜料绿7或颜料绿36;蒽嵌蒽二酮、蒽醌、喹吖啶酮、二嗪、阴丹酮、苝、芘酮和硫靛颜料,尤其是染料索引颜料:颜料黄196、颜料红122、颜料红149、颜料红168、颜料红177、颜料红179、颜料红181、颜料红207、颜料红209、颜料红263、颜料蓝60、颜料紫19、颜料紫23或颜料橙43;三芳基碳颜料,尤其是染料索引颜料:颜料红169、颜料蓝56或颜料蓝61;吡咯并吡咯二酮颜料,尤其是染料索引颜料:颜料红254、颜料红255、颜料红264、颜料红270、颜料红272、颜料橙71、颜料橙73、颜料橙81。
色淀染料也合适,如含有磺酸基团和/或羧酸基团的染料的Ca、Mg和Al色淀颜料。
合适的无机颜料的实例是二氧化钛、硫化锌、氧化锌、铁氧化物、磁铁矿、锰铁氧化物、铬氧化物、群青、镍或铬的锑钛氧化物、锰钛金红石、钴氧化物、钴和铝的混合氧化物、金红石混合相颜料、稀土元素硫化物、由锌和钴与镍形成的尖晶石、含铜锌以及锰的铁基和铬基尖晶石、钒酸铋和混合颜料。特别使用染料索引颜料:颜料黄184、颜料黄53、颜料黄42、颜料黄棕24、颜料红101、颜料蓝28、颜料蓝36、颜料绿50、颜料绿17、颜料黑11、颜料黑33和颜料白6。经常还优选使用无机颜料的混合物。通常也使用有机颜料与无机颜料的混合物。
合适的填料的实例是细分矿石、矿物和难溶性或不溶性盐,如碳酸盐、碳酸钙、白云石、二氧化硅、石英、方石英、硅藻土、硅酸盐、硅酸铝、二氧化硅、滑石、高岭土、云母、长石和硫酸钡。经常也优选使用填料混合物。也经常使用有机和/或无机颜料与填料的混合物。仅含有一种或多种填料的配制剂例如用于颜料制剂的混合以建立所需的性质状况,如颜料含量、流变学、密度或相容性。
组分(B)
(B)是含有至少结构单元(I)和(II)的阴离子共聚物。
(B)的结构单元(I)在一个优选实施方案中是丙烯酸或甲基丙烯酸或其盐,更优选甲基丙烯酸或其盐。
一般而言,结构单元(I)的比例为40至95摩尔%,优选45至85摩尔%。
(B)的结构单元(I)的盐在一个优选实施方案中是碱金属盐,更特别是钠或钾盐,以及铵盐。
(B)的结构单元(II)对应于式(B1)。一般而言,结构单元(II)的比例为5至60摩尔%,优选15至55摩尔%。
在式(B1)中,R11、R12和R13优选互相独立地选自H或甲基。R12尤其优选是甲基。R11和R13尤其优选是H。
在式(B1)中,R4优选是H或甲基。R4尤其优选是H。
在式(B1)中,X优选是O或C(O)O。更优选地,X是C(O)O且R12是甲基。
在式(B1)中,Z优选是亚丙基和苯基亚乙基。具有苯基亚乙基的结构单元(Z-O)对应于式(2)
在式(B1)中,m是0至100的整数,优选1至10,更优选2至5的整数,例如3或4。
在式(B1)中,n是1至100的整数,优选5至45的整数。n尤其优选是8至14的整数。
在式(B1)中,(m+n)优选是8至49的整数。(m+n)尤其优选是11至18的整数。
组分(C)
组分(C)是(C)含有至少一种具有芳族基团的结构单元和至少一种具有聚氧化亚乙基基团的结构单元的非离子共聚物。组分(C)具有有机或无机颜料的分散剂的作用。
在一个优选实施方案中,共聚物(C)不仅包含至少一种具有聚氧化亚乙基基团的结构单元,还包含具有衍生自氧化苯乙烯的芳族基团的结构单元。
特别优选的是如WO-2020/152093中所述的共聚物(C)。在这一特别优选的实施方案中,共聚物(C)对应于式(3)、式(4)或其混合物
其中
n是大于或等于1,优选等于1的整数,
R1是具有1至10个碳原子的脂族直链或支链烃基、氢原子、结构单元-O-X或结构单元-CH2-O-X,优选氢原子,
X对应于式(5)
其中
o是1至50的整数,优选是1至4的整数,
p是1至200的整数,优选是10至25的整数,和
(o+p)大于2,优选是2至250的整数。
尤其优选地,(o+p)是11至29的整数。
特别优选的是如DE-102007032185中所述的用聚醚胺改性的苯乙烯和马来酸酐的共聚物(C)。在这一特别优选的实施方案中,共聚物(C)对应于式(6)
其中
q是1至4的整数,更优选是1至2的整数,
s是5至50的整数,更优选是5至20的整数,
R5是H或具有1至4个碳原子的烷基,更优选甲基,
t是0至10的整数,更优选是1至4的整数,
u是1至100的整数,更优选是10至50的整数,和
t+u大于10。
由于它们的非离子性质,类型(C)的共聚物几乎仅可用于有机颜料配制剂,并且经常对无机颜料不起作用。
组分(D)
作为组分(D),例如使用促进颜料润湿(润湿剂)的阳离子型、阴离子型、两性或非离子型化合物。这些优选是基于含氟表面活性剂、改性氟丙烯酸酯或有机改性的有机硅的所谓基底润湿剂或流平助剂。
组分(E)
作为本发明的颜料制剂的组分(E)使用适用于生产水性颜料分散体的常规分散剂和表面活性剂或此类物质的混合物。为此通常使用阴离子型、阳离子型、两性或非离子型表面活性剂。已经证明特别成功的是,分散剂含有一个或多个中链或长链的或一些具有芳环基团的烃链。其实例是烷基硫酸盐,如十二烷基硫酸盐、硬脂基硫酸盐或十八烷基硫酸盐,伯烷基磺酸盐,如十二烷基磺酸盐和仲烷基磺酸盐,尤其是C13-C17链烷磺酸酯的钠盐;烷基磷酸盐、烷基苯磺酸盐,如十二烷基苯磺酸,以及这些化合物的所有盐。进一步适合作为本发明的颜料制剂的组分(E)的是大豆卵磷脂,和脂肪酸与牛磺酸或羟基乙磺酸的缩合产物,以及蓖麻油树脂酯、脂肪醇、脂肪胺、脂肪酸和脂肪酸酰胺的烷氧基化产物。这些烷氧基化产物也可以是离子型的,并包含例如磺基琥珀酸半酯、磺酸酯、硫酸酯和磷酸酯及其盐、磺酸盐、硫酸盐或磷酸盐作为端基。借助聚乙二醇单(甲基)丙烯酸酯或聚丙二醇单(甲基)丙烯酸酯的大分子单体制备的非离子共聚物,以及类似地,由氧化苯乙烯和聚环氧烷单元组成的阴离子改性嵌段共聚物也是合适的。
组分(F)
组分(F)对应于有机溶剂、助水溶剂或助留剂,其充当增溶剂或提高耐干性。这些可以是例如以下化合物或其混合物:一元醇或多元醇、它们的醚和酯,实例是烷醇,尤其具有1至4个碳原子,例如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇;二元醇或三元醇,尤其具有2至5个碳原子,例如乙二醇、丙二醇、1,3-丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,6,6-己三醇、甘油、二乙二醇、二丙二醇、三乙二醇、聚乙二醇、三丙二醇、聚丙二醇;多元醇的低碳烷基醚,例如乙二醇单甲基醚、乙基醚或丁基醚、三乙二醇单甲基醚或乙基醚;酮和酮醇,如丙酮、甲乙酮、二乙酮、甲基异丁基酮、甲基戊基酮、环戊酮、环己酮、双丙酮醇;乙二醇和丙二醇的共聚物。
组分(G)
组分(G)包含对粘度和流变学有益的一系列不同的添加剂,例如流变改性添加剂或抗沉降剂。作为用于调节粘度的试剂,可以使用如聚乙烯醇和纤维素衍生物之类的化合物。同样可以考虑水溶性天然或合成的树脂和聚合物作为用于提高粘附强度和耐磨强度的成膜剂或粘结剂。有机或无机的碱和酸用作pH调节剂。优选的有机碱是胺,例如乙醇胺、二乙醇胺、三乙醇胺、N,N-二甲基乙醇胺、二异丙基胺、氨基甲基丙醇或二甲基氨基甲基丙醇。优选的无机碱是氢氧化钠、氢氧化钾、氢氧化锂或氨。植物和动物来源的脂肪和油也可对应于组分(G),例如牛脂、棕榈仁脂、椰子油、菜籽油、葵花籽油、亚麻籽油、棕榈油、大豆油、花生油、鲸油、棉籽油、玉米油、罂粟油、橄榄油、蓖麻油、红花油、黄豆油、鲱鱼油和沙丁鱼油。饱和和不饱和脂肪酸也是相对常见的添加剂,例如棕榈酸、癸酸、肉豆蔻酸、月桂酸、硬脂酸、油酸、亚油酸、亚麻酸、己酸、辛酸、花生酸、山萮酸、棕榈油酸、鳕油酸、芥酸和蓖麻油酸及其盐用作颜料表面改性剂。
此外,可以使用光稳定剂,例如苯并三唑、樟脑、羟基二苯甲酮、羟苯基三嗪、草酰苯胺、水杨酸或肉桂酸的衍生物,以及自由基清除剂,例如受阻胺光稳定剂(HALS)。可使用基于四甲基哌啶的衍生物以及基于柠檬酸的抗氧化剂。组分G还可以包括基于矿物油或基于有机硅衍生物的消泡剂系列。
组分(H)
水,用于生产颜料制剂的组分(H),优选以蒸馏水或去离子水的形式使用。同样可以使用饮用水(自来水)和/或天然来源的水。
该颜料制剂具有高颜色强度和低发泡倾向。它们的粘度小于1.0Pas,优选小于0.7Pas,更优选小于0.5Pas。该颜料制剂可以与不同链长的醇(优选乙醇)以任何比例混合,而不使颜料粒子凝聚或絮凝。该颜料制剂具有良好的储存稳定性。
此外,本发明的颜料制剂可以在不用烷基酚、三苯乙烯基酚、酚醛清漆和双酚A衍生物以及伯胺和仲胺的情况下生产。
本发明还涉及一种生产这样的颜料制剂的方法,其中在水(H)和组分(B)和(C)存在下预先加入粉末、颗粒或含水滤饼形式的组分(A),并且任选与(D)、(E)、(F)和(G)一起进行分散,所得水性颜料分散体任选用水(H)稀释。使用分散单元或不同分散单元的组合,优选搅拌球磨机,将颜料以及组分(B)和(C)的混合物分散,所述分散单元在10m/s的搅拌器圆周速度下和在直径小于或等于1.2mm,优选小于或等于0.8mm的非金属研磨介质的作用下运行,所述研磨介质在水的存在下细分散或是细分的。其它添加剂可以是已存在的和/或随后在分散步骤中加入。
本发明还涉及本发明的颜料制剂作为着色剂用于着色和染色各种天然和合成材料的用途,所述材料尤其是水性涂料、色漆、乳胶漆和清漆(水性漆)、水可稀释漆、釉、漆和木材保护体系、印刷油墨,在此例如纺织品印刷、柔性版印刷、装饰印刷或凹版印刷油墨、电子照相墨粉和显影剂,例如单组分或双组分的墨粉(也称为单组分或双组分显影剂)、磁性调色剂、液体调色剂、胶乳调色剂、聚合调色剂以及特种调色剂、墨,优选喷墨用墨,例如水基或非水基(“溶剂基”)的那些,微乳液墨、UV可固化墨和根据热熔法工作的那些墨、用于书写用具如彩色铅笔芯、纤维尖笔、细线笔、毡尖笔、凝胶辊、文本标记笔或白板标记笔的墨,以及绝缘材料如玻璃棉。
此外,本发明的颜料制剂适用于将例如由天然和合成纤维材料组成的各种大分子材料着色。其它应用是肠衣、种子、肥料、玻璃,尤其是玻璃瓶,铺路材料、混凝土、木材染剂、蜡、石蜡、墨、笔用浆料、粉笔、衣物洗涤剂和清洁剂、鞋护理产品、胶乳产品、磨料的着色,用于粘胶纺丝着色,以及用于塑料或各种高分子材料的着色。高分子有机材料是例如纤维素醚和酯,如乙基纤维素、硝化纤维素、乙酸纤维素或丁酸纤维素,天然树脂或合成树脂,如聚合树脂或缩合树脂,例如氨基塑料,尤其是脲和三聚氰胺-甲醛树脂,醇酸树脂、丙烯酸系树脂、酚醛塑料、聚碳酸酯、聚烯烃如聚苯乙烯、聚氯乙烯、聚乙烯、聚丙烯、聚丙烯腈、聚丙烯酸酯、聚酰胺、聚氨酯或聚酯、橡胶、酪蛋白、胶乳、有机硅,单独地或以混合物形式。
本发明的颜料制剂还可另外用作“平面显示器”的滤色器(“滤色片”)的着色剂,以及用于加法色生成和减法色生成的添加剂,还用于“光致抗蚀剂”,以及用作电子墨(“电子墨水”或“e-墨”)或电子纸(“电子纸”或“e-纸”)的染料。
定义
“水溶性”涉及在25℃下在0.1重量%的浓度下具有足够溶解性以得到目视清澈溶液的材料。术语“水不溶性”涉及非“水溶性”的材料。
“单体”是指在引发剂或合适的反应(例如自由基聚合)存在下生成大分子的离散的、未聚合的化学单元。“单元”表示已经聚合,即作为聚合物的一部分的单体。
“聚合物”是指由一种、两种或更多种单体的聚合形成的化学品。术语“聚合物”包括所有源自单体聚合的材料以及天然聚合物。仅由一种单体类型制成的聚合物被称为均聚物。在此,聚合物包含至少两种单体单元。由两种或更多种不同类型的单体形成的聚合物被称为共聚物。不同单体的分布可以是无规的、交替的或嵌段的。后者随之形成所谓“嵌段共聚物”。如果已有聚合物的主链用另外的不同聚合物官能化,则产生所谓“梳状共聚物”或“接枝共聚物”。本文所用的术语“聚合物”包括任何类型的聚合物,包括均聚物和共聚物。
缩写
C.I.“染料索引”
n.m.无法测得
NT非触变,颜料制剂表现出牛顿行为
LT轻微触变,颜料制剂表现出轻微的非牛顿行为
T触变,颜料制剂表现出明显的非牛顿行为
具体实施方式
实施例
示例性颜料制剂的成分
组分(A)
有机颜料
A1 Hansa亮黄2GX 70-S(C.I.颜料黄74,PY 74)
A2黄HR 03LV 5462(C.I.颜料黄83,PY 83)
A3紫RL 02(C.I.颜料紫23,PV 23)
A4永固红FGR(C.I.颜料红112,PR 112)
A6红D3G 70(C.I.颜料红254,PR 254)
A7蓝A4R(C.I.颜料蓝15:1,PB 15:1)
A8蓝B2G-EDS VP3491(C.I.颜料蓝15:3,PB 15:3)
A9绿GNX(C.I.颜料绿7,PG 7)
A10300(C.I.颜料黑7,PBk 7)
无机颜料
A113920(C.I.颜料黄42,PY 42)
A12橙L 2430(C.I.颜料橙82,PO 82)
A13黄L 1100(C.I.颜料黄184,PY 184)
A14红130M(C.I.颜料红101,PR 101)
A152160(C.I.颜料白6,PW 6)
分散剂组分(B)
B由49摩尔%甲基丙烯酸和51摩尔%聚二醇MA750组成的无规共聚物
分散剂组分(C)
C1由1摩尔%甘油和14摩尔%氧化苯乙烯和85摩尔%环氧乙烷组成的支化嵌段共聚物(根据WO-2020152093)
C2由苯乙烯/马来酸酐共聚物(Cray Valley SMA 2000,比例2:1苯乙烯/马来酸酐)与1当量Jeffamine M-2005的反应产物组成的接枝共聚物(来自Huntsman公司)
对比分散剂
VD1FX 600(Elementis),一种多官能聚合物分散剂,推荐用于无机和有机颜料。Nuosperse FX 600是EP1599549B1中描述的聚马来酸铵盐。
VD2Ultra 4290(BASF),一种适用于在水性制剂中的有机和无机颜料的高分子分散剂。Dispex Ultra 4290是一种高分子分散剂/共聚物,其酸值为9mg KOH/g,大概基于聚丙烯酸酯。
VD3LFS(Clariant),一种含有阴离子表面活性剂并且旨在用于水基颜料制剂的分散剂,其适用于所有颜料。
VD4ECS(Clariant),一种含有阴离子表面活性剂并且旨在用于水基颜料制剂的分散剂,其适用于所有颜料。
VD5Dispers 750W(Evonik)是一种用于高品质水性配制剂的弱阴离子型聚合物润湿和分散添加剂。其具有非常好的相容性并适用于所有类型的颜料,特别是无机颜料。
在Lau分散机中或在Dispermat中生产颜料制剂。
在Lau分散机中生产颜料制剂:
液体组分(去离子水、分散剂、添加剂)使用振荡器(例如Heidolph Unimax 2010)均化。随后将粉末、颗粒或滤饼形式的颜料与液体预混物一起用漆振荡器(例如LauDisperser DAS)均化和预分散。使用漆振荡器(例如Lau Disperser DAS)进行随后的细分散,其中用尺寸d=3mm的玻璃珠以60分钟的规定运行时间进行研磨。使用离心机(例如Heraeus Multifuge 3s)分离除去研磨介质并分离颜料制剂。
在Dispermat中生产颜料制剂:
使用溶解器(例如来自VMA Getzmann GmbH,AE3-M1类型)或其他合适的装置,将粉末、颗粒或滤饼形式的颜料与分散剂和其它添加剂一起在去离子水中均化和预分散。使用珠磨机(例如使用来自VMA-Getzmann GmbH的AE3-M1)或其它合适的分散单元进行随后的细分散,其中使用尺寸d=1.2-1.4mm的硅酸锆或氧化锆珠进行研磨,直至希望的颜色强度、颜色和透明度。然后用去离子水将分散体调节至所需的最终颜料浓度,分离除去研磨介质并分离颜料制剂。
以下实施例(表1和2)中描述的颜料制剂通过上述方法生产,其中各个成分以所报道的量使用以得到100份各自的颜料制剂。在所有实施例中,份数表示重量份。
颜料制剂的表征:
粘度使用来自Anton Paar GmbH的锥板粘度计(MCR 72)(钛锥:直径60mm,1°)在20℃下测定,其中测量粘度对于在0至200s-1的范围内的剪切速度的依赖关系。在60s-1的剪切速度下评定各样品的粘度。
基于光谱测量测定颜色强度。为此,制造浆料在白色乳胶漆中的2%调色物。使用间隙高度为120μm的拉膜刮刀涂布器将该调色物施加到试验基底上并干燥过夜。使用分光光度计测量该有色刮涂膜的色值。由测得的色值根据ISO 787-26计算颜色强度。
为了评估分散体的储存稳定性,在制剂制成后即刻和在50℃下储存14天后测量粘度。另外,相对于在室温下储存的样品测定由此储存的样品的颜色强度。此外,通过测定形成的底部淀渣以及上清液来评定储存样品的均匀性和沉降行为。
评价:
基于以下4个参数进行评价:触变性、稳定性、粘度和颜色强度。如下所述进行分级:
触变性:NT=非触变,浆料没有形成结构粘度,即在储存条件下没有变得更粘稠或甚至变成固体。LT=轻微触变,浆料在储存时产生提高的粘度或甚至变得不可流动。但是,在例如剪切形式的仅少量能量的作用下,浆料可以再次流态化。T=触变,浆料在储存条件下固化并且不再可流动,但在增加能量输入时再次暂时变成可流动的。
稳定性:3=浆料即使在储存期间也是均匀的,既没有形成上清液也没有形成沉降。2=浆料在储存期间在表面上形成可以容易地搅拌的上清液或在底部形成沉降物。1=浆料在储存期间形成两相,或在底部形成沉降物,其仅可困难地或不可能搅拌。
粘度:粘度的评价高度依赖于待分散的颜料。一般目的是生产可流动颜料浆。其粘度通常在50至1000mPa*s的目标范围内。
颜色强度:在储存14天后,相对于参考产品的值测量色值。大于100%的颜色强度是优于参考产品的。白色颜料浆是例外,其中低于100%的值是优于参考产品的。
基于以下4个等级进行综合评价:
更好:所有参数在所需范围内(至少~OK),但优于标准分散剂(所用的标准分散剂:用于有机颜料和炭黑颜料的Dispersogen LFS,用于无机颜料的Dispersogen ECS)
OK:所有参数在所需范围内,与标准分散剂相当
几乎OK(~OK):一个参数不满足(制剂经常表现出轻微触变性,并且颜色稍弱于用标准分散剂制成的制剂);
不OK(NOK):至少2个参数不满足(制剂表现出高粘度、稳定性问题,并且颜色明显弱于用标准分散剂制成的制剂)
向表1的所有实施例中加入10.0份组分(E,丙二醇)、0.2份组分(F,防腐剂)、0.3份组分(G,消泡剂)和补偿组分(H,去离子水)。
来自表1的实施例的数值清楚地显示出与可购得的已知通用分散剂相比,本发明的混合物的改进的、尤其是通用的性能。
实施例133-135
来自表2的实施例的数值清楚地表明,本发明的混合物还具有由单个组分无法预见的协同效应。因此,有机颜料黄PY 74(A1)与B2的颜料制剂表现出严重的不相容性和高粘度。虽然使用C2的制剂具有OK评价,但表现出略弱的颜色。质量比为85/15的B2/C2混合物产生具有很低粘度和很好的相容性以及大幅改进的颜色强度的稳定颜料制剂。对于其它有机颜料例如颜料红PR 112(A4)和炭黑(A10)以及对于无机颜料PY 42(A11),可以观察到类似的协同效应。
Claims (19)
1.一种颜料制剂,其包含
(A)至少一种有机和/或无机颜料和/或填料;
(B)至少一种阴离子共聚物作为分散剂,其含有
(I)40至95摩尔%的阴离子单体的结构单元,所述阴离子单体选自丙烯酸、甲基丙烯酸、衣康酸、2-羧乙基丙烯酸、马来酸、其混合物及其各自的盐,优选甲基丙烯酸或其盐,和
(II)5至60摩尔%的具有式(B1)的重复单元的单体的结构单元
其中
R11、R12和R13互相独立地选自H、甲基和乙基,
R4是H或具有1至4个碳原子的烷基,
X选自O、COO、CONH、CH2O或CH2CH2O,
Y是亚乙基
Z是亚丙基、亚丁基或苯基亚乙基,
m是0至100的整数,
n是1至100的整数,和
m+n大于5,和
(C)至少一种非离子共聚物,其含有至少一种具有芳族基团的结构单元和至少一种具有聚乙二醇基团的结构单元,和
(H)水。
2.根据权利要求1所述的颜料制剂,其中(B)的结构单元(I)是丙烯酸或甲基丙烯酸或其盐,更优选甲基丙烯酸或其盐。
3.根据权利要求1和/或2所述的颜料制剂,其中结构单元(I)的比例为45至85摩尔%。
4.根据权利要求1至3中一项或多项所述的颜料制剂,其中结构单元(II)的比例为15至55摩尔%。
5.根据权利要求1至4中一项或多项所述的颜料制剂,其中R11、R12和R13互相独立地选自H或甲基。
6.根据权利要求1至5中一项或多项所述的颜料制剂,其中R12是甲基,且R11和R13是H。
7.根据权利要求1至6中一项或多项所述的颜料制剂,其中是H或甲基。
8.根据权利要求1至7中一项或多项所述的颜料制剂,其中X是O或C(O)O。
9.根据权利要求1至8中一项或多项所述的颜料制剂,其中Z是亚丙基或苯基亚乙基。
10.根据权利要求1至9中一项或多项所述的颜料制剂,其中m是1至10,更优选2至5的整数,例如3或4。
11.根据权利要求1至10中一项或多项所述的颜料制剂,其中n是5至45,更优选8至14的整数。
12.根据权利要求1至11中一项或多项所述的颜料制剂,其中(m+n)是8至49的整数。
13.根据权利要求1至12中一项或多项所述的颜料制剂,其中所述共聚物(C)不仅包含至少一种具有聚氧化亚乙基基团的结构单元,还包含具有衍生自氧化苯乙烯的芳族基团的结构单元。
14.根据权利要求1至12中一项或多项所述的颜料制剂,其中所述共聚物(C)对应于式(3)、式(4)或其混合物
其中
n是大于或等于1,优选等于1的整数,
R1是具有1至10个碳原子的脂族直链或支链烃基、氢原子、结构单元-O-X或结构单元-CH2-O-X,优选氢原子,
X对应于式(5)
其中
o是1至50的整数,优选是1至4的整数,
p是1至200的整数,优选是10至25的整数,和
(o+p)大于2,优选是2至250的整数。
15.根据权利要求1至12中一项或多项所述的颜料制剂,其中所述共聚物(C)对应于式(6)
其中
q是1至4的整数,更优选是1至2的整数,
s是5至50的整数,更优选是5至20的整数,
R5是H或具有1至4个碳原子的烷基,更优选甲基,
t是0至10的整数,更优选是1至4的整数,
u是1至100的整数,更优选是10至50的整数,和
t+u大于10。
16.根据权利要求1至15中一项或多项所述的颜料制剂,其中所述颜料制剂包含5至80重量%的组分(A)。
17.根据权利要求1至16中一项或多项所述的颜料制剂,其中所述颜料制剂包含1至20重量%的组分(B)。
18.根据权利要求1至17中一项或多项所述的颜料制剂,其中所述颜料制剂包含1至20重量%的组分(C)。
19.聚合物(B)和(C)的组合在颜料制剂的生产中作为分散剂的用途,其中
(B)是阴离子共聚物,其含有
(I)40至95摩尔%的阴离子单体的结构单元,所述阴离子单体选自丙烯酸、甲基丙烯酸、衣康酸、2-羧乙基丙烯酸、马来酸、其混合物及其各自的盐,优选甲基丙烯酸或其盐,和
(II)5至60摩尔%的具有式(B1)的重复单元的单体的结构单元
其中
R11、R12和R13互相独立地选自H、甲基和乙基,
R4是H或具有1至4个碳原子的烷基,
X选自O、COO、CONH、CH2O或CH2CH2O,
Y是亚乙基
Z是亚丙基、亚丁基或苯基亚乙基,
m是0至100的整数,
n是1至100的整数,和
m+n大于5,和
(C)是非离子共聚物,其含有至少一种具有芳族基团的结构单元和至少一种具有聚乙二醇基团的结构单元,
所述颜料制剂包含
(A)至少一种有机和/或无机颜料和/或填料,和
(H)水。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP21174871.0 | 2021-05-20 | ||
EP21174871.0A EP4092088A1 (de) | 2021-05-20 | 2021-05-20 | Universelle dispergiermittel für anorganische und organische pigmente |
PCT/EP2022/051180 WO2022242917A1 (de) | 2021-05-20 | 2022-01-20 | Universelle dispergiermittel für anorganische und organische pigmente |
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CN117242139A true CN117242139A (zh) | 2023-12-15 |
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EP (2) | EP4092088A1 (zh) |
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DE930655C (de) | 1953-06-10 | 1955-07-21 | Phoenix Gummiwerke Ag | Verfahren zum festen Verbinden von Kautschuk oder Kunststoffen mit festen Koerpern und untereinander |
US5340394A (en) | 1992-07-23 | 1994-08-23 | The Glidden Company | Zero voc tinting concentrates for decorative paints |
DE9306055U1 (de) * | 1993-04-21 | 1994-08-25 | Imperial Chemical Industries Plc, London | Wässerige nicht-verstopfende Abtönfarbe für Anstrichfarben o.dgl. |
DE19950043A1 (de) * | 1999-10-16 | 2001-07-12 | Degussa | Pigmentpräparationen, Verfahren zu ihrer Herstellung und Verwendung |
DE10309813B4 (de) | 2003-03-05 | 2008-06-19 | Heubach Gmbh | Pigmentzubereitung und Verfahren zu deren Herstellung |
WO2006102011A1 (en) | 2005-03-18 | 2006-09-28 | Valspar Sourcing, Inc. | Low voc universal paint colorant compositions |
DE102005019384A1 (de) * | 2005-04-26 | 2006-11-02 | Süd-Chemie AG | Polymere für die Dispersion von Pigmenten und Füllstoffen |
DE102007032185A1 (de) | 2007-07-11 | 2009-01-15 | Clariant International Limited | Pigmentzubereitungen mit polymeren Dispergiermitteln |
JP5101394B2 (ja) * | 2008-05-27 | 2012-12-19 | 株式会社リコー | 記録用インク用色材分散体及びこれを用いた記録用インク |
DE102012013046A1 (de) | 2012-06-29 | 2014-01-02 | Clariant International Ltd. | Fettsäurekondensationsprodukte als Dispergiermittel in Pigmentpräparationen |
CN107922749B (zh) | 2015-08-20 | 2020-09-04 | 巴斯夫欧洲公司 | 用于销售点使用的通用颜料制剂 |
DE102019200789A1 (de) | 2019-01-23 | 2020-07-23 | Clariant International Ltd | Wasserbasierende Pigmentpräparationen, ihre Herstellung und Verwendung |
-
2021
- 2021-05-20 EP EP21174871.0A patent/EP4092088A1/de not_active Withdrawn
-
2022
- 2022-01-20 EP EP22701929.6A patent/EP4341353A1/de active Pending
- 2022-01-20 CN CN202280032189.5A patent/CN117242139A/zh active Pending
- 2022-01-20 WO PCT/EP2022/051180 patent/WO2022242917A1/de active Application Filing
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EP4092088A1 (de) | 2022-11-23 |
EP4341353A1 (de) | 2024-03-27 |
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