CN112584922B - 芳香族酰胺分散剂 - Google Patents
芳香族酰胺分散剂 Download PDFInfo
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- CN112584922B CN112584922B CN201980055029.0A CN201980055029A CN112584922B CN 112584922 B CN112584922 B CN 112584922B CN 201980055029 A CN201980055029 A CN 201980055029A CN 112584922 B CN112584922 B CN 112584922B
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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
- 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
- C09D11/10—Printing inks based on artificial resins
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/22—Amides or hydrazides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G65/2618—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 nitrogen
- C08G65/2621—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 nitrogen containing amine groups
- C08G65/2624—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 nitrogen containing amine groups containing aliphatic amine groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
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Abstract
本发明涉及一种聚合分散剂和一种组合物,所述聚合分散剂在芳香族锚定基团与增溶性链之间含有叔酰胺键,所述组合物含有颗粒状固体、水性或极性有机介质以及聚合芳香族酰胺分散剂,所述聚合芳香族酰胺分散剂具有通过酰胺的羰基与芳环上带有的两个或更多个残余羧酸基或其上带有的磺酸基和残余羧酸基连接的至少一个叔酰胺连接基团。本发明进一步提供了含有所述分散剂的用于漆浆、分散体、涂料和油墨的组合物。
Description
技术领域
本发明涉及一种聚合芳香族酰胺分散剂、含有颗粒状固体、水性介质或极性有机介质的组合物以及具有芳环的聚合分散剂,所述芳环具有通过叔酰胺键化学与增溶性聚合物链的酸官能团连接。本发明进一步提供了含有所述分散剂的用于漆浆、分散体、涂料(包含油漆)和油墨的组合物。
背景技术
如油墨、油漆和漆浆等许多调配物需要有效地将颗粒状固体均匀地分散在水性或极性有机介质中的分散剂。对于油墨,期望油墨制造商产生分辨率和质量较高的印刷产品。使印刷工艺适于迎合基材、树脂和颜料的不断扩大的范围具有挑战性。颜料分散体应与所用的不同调配物相容,以确保最终涂料具有良好的附着力和耐性。颜料分散性或稳定性差可能导致极性有机液体介质或水性液体介质内发生团聚或沉降。
PCT专利公开WO 2008/028954公开了在极性和非极性有机介质中均含有末端酸性基团的酰亚胺分散剂化合物,其中分散剂化合物由以下结构表示:
其中T为-(CH2)3-或-CH2CH(CH3)-;
R'为H或C1-50-任选取代的烃基或C1-50-任选取代的烃羰基;
Y为C2-4-亚烷基氧基;
x为2到90;并且
q为1或2。
美国专利5,688,312公开了一种在约125℃到180℃的温度下的粘度为约1厘泊到10厘泊的油墨组合物,所述油墨组合物包含着色剂和酰亚胺或双酰亚胺。所述酰亚胺或双酰亚胺可以通过使邻苯二甲酸酐与单胺或二胺反应来制备。所述单胺可以是例如十二烷基胺或硬脂胺。所述二胺可以是1,12-十二烷二胺。
PCT专利公开WO 2007/139980公开了至少一种二酐与彼此不同的至少两种反应物的反应产物,所述反应物中的每种反应物都含有伯或仲氨基、羟基或硫醇官能团,并且所述反应物中的至少一种反应物是聚合的。所述反应产物可用于如油墨和涂料等组合物中。
美国专利6,440,207公开了一种用于通过以下制备用于水性体系的可分散的干燥有机颜料的方法:(a)研磨含有以下的混合物:(1)一种或多种有机颜料;(2)相对于所述有机颜料至少约1重量%的一种或多种芳香族聚(环氧烷)分散剂;(3)相对于所述有机颜料0重量份到约10重量份的研磨液,所述有机颜料基本不溶于所述研磨液;(4)相对于所述有机颜料0重量%到约50重量%的除分散剂(2)以外的一种或多种研磨添加剂;和(5)相对于所述有机颜料0重量%到约20重量%的一种或多种表面处理添加剂;(b)任选地向经研磨的颜料中添加(6)一种或多种液体,所述有机颜料基本不溶于所述一种或多种液体,所述一种或多种液体的量使得总固体含量不会降低到低于约10%和(7)一种或多种多价金属盐和/或一种或多种季铵盐;以及(c)分离经研磨的有机颜料。芳香族聚(环氧烷)分散剂可以通过以下制备:在含有250g去离子水、19.8g(0.100mol)1,8-萘二甲酸酐和105g(0.105mol)JeffamineTM XTJ-506(83wt%的环氧乙烷,17wt%的环氧丙烷)的高压釜中进行反应。将高压釜密封,在搅拌下加热到150℃,并在150℃下保持五小时。反应冷却后,将所得棕色液体排入烧杯中,然后向其中添加15g脱色木炭。搅拌过夜后,将悬浮液过滤,并将滤饼用水洗涤,从而得到大约500g固体含量为23.63%的琥珀色滤液。干燥颜料可以用于水基油漆体系中。
美国专利公开2008/0202382描述了一种聚醚甲基丙烯酸酯和聚胺的迈克尔反应(Michael reaction)用于分散超细颗粒的用途。本发明涉及用于有机分散体的胺分散剂和含有这种分散剂的涂料组合物。
美国专利公开2015/112020描述了一种稠合的芳香族酰亚胺侧基作为由以下结构表示的颜料分散剂的锚点的用途:
其中R1为Q环上可用于与取代基键合的任何位置中的并且独立地由至少一个吸电子基团表示的取代基,a为1或2。W为氧、硫、NH或NG。R2为C1-20亚烃基(hydrocarbylenegroup)或C1-20亚烃基(hydrocarbonylene group),其中R2含有多于2个碳原子并且可以为直链或支链。R3为H或与聚合物链的末端氧原子键合从而形成末端醚或酯的C1-50任选取代的烃基。Pol是环氧乙烷的均聚物链或环氧乙烷的共聚物链,其中环氧乙烷占由聚醚或聚酯组成的共聚物链的40wt%到99.99wt%。
发明内容
本发明的一个目的是提供一种能够使具有无机和有机颜料的分散体具有低粘度和胶体稳定性的分散剂。通过提供更高的胶体稳定性,可以提高色强度,改善其它着色性能,增加颗粒状固体负荷,形成改进的分散体,提高亮度,产生粘度降低的组合物,保持稳定分散,减小粒度,减小粒度分布,降低雾度,提高光泽度,提高色强度并增加喷射度(尤其是当组合物包含无机颜料或填料时)。本发明的组合物还可以在环境储存条件和高温储存条件下表现出胶体稳定性。
最近发现,使如聚醚胺等伯胺封端的增溶性链首先与丙烯酸酯反应,然后与酸官能化的芳香族二羧酸或聚羧酸的酸酐反应是有利的,因为可以仅形成酰胺(而不形成酰亚胺)。除有机和炭黑颜料外,芳环上的所产生的游离羧基显著增强了无机颜料上的分散性能。
芳香族酰胺功能分散剂
一种分散剂包括具有以下结构的分散剂聚合物:
式I
R1独立地为CO2H或SO3H,其中a为1到2或3;
R2为H或C1-50任选取代的烃基或C1-50任选取代的烃羰基;
G为任选地被表示为醚、酯、醛、酮、酰胺、尿烷、醇或羧酸基的O或氮等杂原子取代的C1-50烃基,或任选取代的(甲基)丙烯酸烷基酯或(甲基)丙烯酰胺的残基(指定反应物种的化学反应的预期反应和/或聚合产物),或下式表示的环氧化物的开环产物:
其中R6在每次出现时可以单独地为H或CH3或C2H5或以下基团之一:
其中D为C1-5烷基、CN、OH、NO2、NH2、卤素、CO2H、SO3H、CH3或OCH3;并且p为0到4;
R3为直链或支链的C1-50烷基,并且优选地为C1-20烷基;
其中T为-C(O)-CH(R4)CH2或C1-5烃基链;
当G为C1-50烃基时,T为-C(O)-CH(R4)CH2;
当G是丙烯酸酯的残基(指定反应性物种的化学反应的预期反应和/或聚合产物)或环氧化物时,T为C1-5烃基链;
R4为H或Me,优选地为H;
Y在每个重复单元中独立地为C2-4亚烷基氧基;
Q为包括一个或多个芳环的亚烃基,所述一个或多个芳环被R1取代,(至多三个或四个环),任选地如果存在两个芳环则环是稠合的,其中与Q连接的羧酸基与Q中的所述芳环的碳原子相连接;
其中所述式中的任何酸的氢可以被金属、胺或铵阳离子替代使所述分散剂呈盐的形式;并且
x为2到90。
在一个实施例中,Q可以基于具有酰胺键的苯环。在一个优选实施例中,Q衍生自1,2,4-苯三羧酸酐。与Q连接的羧酸或磺酸基与Q的芳环碳连接。
具体实施方式
本发明提供了一种分散剂和包括所述分散剂、颗粒状固体(如颜料或填料)和水性或极性有机介质的组合物以及所述颗粒、分散剂和连续介质作为漆浆、油墨、涂料(油漆)的用途。如果用作涂料,则所述组合物可以任选地包含粘结剂。
聚合物链的数均分子量可以为100到10,000、或100到5,000、或300到3,000或400到2,500。
预先制备的聚合物链的数均分子量可以通过GPC分析来测定。原位制备(即,聚合物链从引发物种(引发剂)基团中生长出来)的聚合物的数均分子量可以通过测定与单体[M]和引发剂[I](引发剂是稠合的芳香族酸酐衍生的中间体)的比率成比例的聚合度(DP)来计算并且可以通过式DP=[M]/[I]计算。使用核磁共振(NMR)的分析可以用于测定聚合度并且因此计算分子的聚合基团或聚合物链段的数均分子量。
烃基和亚烃基的定义。如本文所用,术语“亚烃基”以所述术语的一般含义使用并且旨在包含通过从烃中去除两个氢原子而形成的任何二价基团。术语“烃基”或“亚烃基”表示具有与分子的剩余部分直接连接的碳原子并且在本发明的上下文内具有烃或主要烃特性的基团。这种基团包含以下:(1)纯烃基,即脂肪族基团(例如,烷基或烯基)、脂环族基团(例如,环烷基或环烯基)、芳香族基团、脂肪族和脂环族取代的芳香族基团、芳香族取代的脂肪族和脂环族基团等,以及环状基团,其中环通过分子的另一部分完成(即任何两个所指示的取代基可一起形成脂环族基团)。实例包含甲基、乙基、辛基、癸基、十八烷基、环己基、苯基等。(2)经取代的烃基,即含有不会改变基团的主要烃特性的非烃取代基的基团。本领域的技术人员将知道合适的取代基。实例包含羟基、硝基、氰基、烷氧基、酰基等。(3)杂基团,即在特性上主要为烃的同时,在其它方面由碳原子构成的链或环中含有除碳和氢以外的原子的基团。合适的杂原子对本领域的技术人员而言将是显而易见的并且包含例如氮、氧和硫。
如本文所用,术语“亚烃基”旨在包含含有羰基(>C=O)的任何烃基,例如含有酮基或醛基的烃基。通常,亚烃基可以包含-(CH2)5-C(O)-、-(CH2)4-C(O)-、-(CH2)3-C(O)-或-(CH2)2-C(O)-。如本文所用,对亚烃基(hydrocarbylene)或亚烃基(hydrocarbonylenegroup)的引用可以是直链或支链的并且可以是饱和或不饱和的。
公开了一种分散剂,所述分散剂包括具有以下结构的分散剂聚合物:
式I
R1独立地为CO2H或SO3H,其中a为1到2或3;
R2为H或C1-50任选取代的烃基或C1-50任选取代的烃羰基;
G为任选地被呈现为/表示为醚、酯、醛、酮、酰胺、尿烷、醇或羧酸基的O或氮等杂原子取代的C1-50烃基,或任选取代的(甲基)丙烯酸烷基酯或(甲基)丙烯酰胺的残基(指定反应物种的化学反应的预期反应和/或聚合产物),或下式表示的环氧化物的开环产物:
其中R6在每次出现时可以单独地为H或CH3或C2H5或以下基团之一:
其中D为C1-5烷基、CN、OH、NO2、NH2、卤素、CO2H、SO3H、CH3或OCH3;并且p为0到4;
R3为直链或支链的C1-50烷基,并且优选地为C1-20烷基;
T为-C(O)-CH(R4)CH2或C1-5烃基链;
当G为C1-50烃基时,T为-C(O)-CH(R4)CH2;
当G是丙烯酸酯的残基(指定反应性物种的化学反应的预期反应和/或聚合产物)或环氧化物时,T为C1-5烃基链;
R4为H或Me,优选地为H;
Y在每个重复单元中独立地为C2-4亚烷基氧基;
Q为包括一个或多个芳环的亚烃基,所述一个或多个芳环被R1取代,(至多三个或四个环),任选地如果存在两个芳环则环是稠合的,其中与Q连接的羧酸基与Q中的所述芳环的碳原子相连接;
其中所述式中的任何酸的氢可以被金属、胺或铵阳离子替代使所述分散剂呈盐的形式;并且
x为2到90。
在一个实施例中,Q可以基于具有酰胺键的苯环。在一个优选实施例中,Q是衍生自1,2,4-苯三羧酸酐的苯环。与Q连接的羧酸基和任选的磺酸基与Q的芳环的碳原子连接。
实施例1a
聚醚胺与(甲基)丙烯酸酯之间的反应
实施例2a
聚醚胺与环氧化物之间的反应
实施例3a
烷基胺与聚醚(甲基)丙烯酸酯之间的反应
以下是在氮与芳环的羧基反应以形成酰胺键之前加到酰胺键的氮原子的单元的结构。*表示所示结构与氮原子的连接点。这些结构衍生自下文较远处示出的不饱和单体(如各种丙烯酸酯)。
Z为-OH、-N(R7)2(其中R7在每次出现时单独地为C1-5烷基)、C3-6环烷基、碳和氧和/或氮的5、6或7原子杂环;或酸基,如CO2H、SO3H、OPO3H2,U为O或NH,w为1到20,优选地1到10,并且最优选地1-5。D和p如先前所定义,并且x1为1到50,并且更理想地1到20的整数。当用于分散颗粒的介质为或含有大量极性有机溶剂时,w的值优选为1到20。当用于分散颗粒的介质是水时,w的值优选为1到5。
将形成G的单体的实例如下,其中U为O或NH,R2为H或C1-50任选取代的烃基或C1-50任选取代的烃羰基,R3为直链或支链的C1-50烷基,并且优选地为C1-20烷基,R4为H或CH3,R5为H或甲基、乙基、丙基、丁基或苯基、并且x1为1到20。D为C1-5烷基、CN、OH、NO2、NH2、卤素、CO2H、SO3H、CH3和OCH3,并且p为0到4。
将形成G的环氧化物的实例如下:
其中R6在每次出现时可以单独地为H、CH3、C2H5或以下基团:
其中D为C1-5烷基、CN、OH、NO2、NH2、卤素、CO2H、SO3H、CH3或OCH3,并且p为0到4。
分散剂可以具有以下结构:
式IIa
式IIb
式IIc
式IIIa
式IIIb
式IVa
式IVb
式V
其中R6可以为R2、任选取代的苯环、R3-CO2H基团、与任选取代的苯环的醚键或与任选取代的萘稠合的芳环结构的醚键。
Q为具有至少一个且至多3或4个芳环(其可以任选地稠合在一起)的有机结构并且可以基于苯、苯基、联苯或稠合的芳环,如萘或蒽。在一个实施例中,Q可以为衍生自苯甲酸的单个苯环。通常,Q-(R1)a衍生自1,2,4-苯三羧酸酐。
Q可以基于苯、萘、蒽、菲或它们的混合物。在一个实施例中,Q可以基于萘。当Q基于萘时,式I的聚合物链可以具有单或多R1取代的萘酰胺基团,其将萘环上的位置用于取代基和酰胺键,所述位置至少如萘上的1,2;2,3;或1,8位置或这种位置的混合。
当Q基于联苯时,式I的聚合物链可以具有联苯环上使用如4',3,4;5',3,4;3',4',3或这种位置的混合等位置的单或多R1取代。
将形成Q的实例酸酐如下,其中R1为CO2H或SO3H。注意,R1可以存在于芳环中的任何芳环上。
通常,Q衍生自芳香族三羧酸酐,如三羧酸萘酸酐、三羧酸联苯酸酐、三羧酸苯酸酐或它们的混合物。
结构可以通过包括以下的方法制备:使迈克尔受体(Michael acceptor),如(甲基)丙烯酸酯或功能取代的(甲基)丙烯酸酯与亲核性聚合链,如聚醚胺反应,从而形成仲胺,以及然后使仲胺与酸官能化的芳香族二酸或酸酐,如上所述包含三羧酸苯酸酐和磺酸官能化的二羧酸苯酸酐反应,以形成叔酰胺和所呈现的结构发明。第一步骤,即迈克尔反应可以在足够高的激活温度下进行,所述温度例如0℃到150℃或50℃到200℃。形成叔酰胺的第二反应步骤是在足够高的酰胺化温度下进行的,所述温度例如至少50℃或50℃到120℃。
结构可以通过包括以下的方法制备:使聚合丙烯酸酯,如MPEG丙烯酸酯反应,然后与亲核性的脂肪族胺反应,从而形成仲胺,以及使仲胺与酸官能化的芳香族二酸或酸酐,如三羧酸苯酸酐反应,以形成叔酰胺和所呈现的本发明的结构。第一步骤,即迈克尔反应可以在足够高的激活温度下进行,所述温度例如0℃到150℃或50℃到200℃。形成叔酰胺的第二反应步骤是在足够高的酰胺化温度下进行的,所述温度例如至少50℃或50℃到120℃。
结构可以通过包括以下的方法制备:使丙烯酸羟酯,如丙烯酸羟乙酯反应,然后与亲核性的脂肪族胺反应,从而形成仲胺,以及使仲胺与酸官能化的芳香族二酸或酸酐反应,从而形成叔酰胺。然后,使产物与环状酯,如己内酯反应并聚合以形成聚合链。第一步骤,即迈克尔反应可以在足够高的激活温度下进行,所述温度例如0℃到150℃或50℃到200℃。形成叔酰胺的第二反应步骤是在足够高的酰胺化温度下进行的,所述温度例如至少50℃或50℃到120℃。聚合可以在足够高的聚合温度下进行,所述温度例如至少100℃到200℃。
实施例1-具有聚醚链的芳香族酰胺功能分散剂
在实施例1中,使聚醚胺与(甲基)丙烯酸酯(任选取代的)通过迈克尔反应进行反应以产生仲胺,并且然后使仲胺与酸官能化的芳香族酸酐反应。通过式IIa、IIb、IIc、IIIa、IIIb、IVa和IVb对此进行了说明。
R3是与聚合物链的末端氧原子键合从而形成末端醚的C1-50(或C1-20)-任选取代的烃基或与聚合物链的氧原子键合从而形成末端酯基或末端尿烷基的C1-50(或C1-20)-烃羰基(即含有羰基的烃基),并且取代基可以是卤素、醚、酯或它们的混合物;
R5可以是H或H(其量足以提供40wt%到99.99wt%的环氧乙烷基)和甲基、乙基和苯基中的至少一种的混合物。任选取代的(甲基)丙烯酸酯可以是以下示出的(甲基)丙烯酸酯中的任何(甲基)丙烯酸酯,其中变量如先前所定义。
聚醚胺与(甲基)丙烯酸,然后与酸官能化的芳香族酸酐的反应,例如L207与丙烯酸,然后与三羧酸苯酸酐的反应。聚醚胺与(甲基)丙烯酸叔氨基烷基酯,然后与酸官能化的芳香族酸酐的反应,例如L200与丙烯酸二甲氨基乙酯,然后与三羧酸苯酸酐的反应。
聚醚的数均分子量可以为100到10,000、100到5,000、或300到3,000或400到2,500。聚醚胺可以通过以下制备:使单醇引发剂仅与环氧乙烷反应或与环氧乙烷和环氧丙烷的混合物反应以形成醇封端的聚合物链,然后将醇封端的聚合物链转化为胺。聚醚胺可以通过氨基醇的烷氧基化来获得,如美国专利5,879,445(具体地第2栏第50行到第7栏第50行中的公开内容)中所述。
对于水性分散体(50-100%水),聚醚可以例如是环氧乙烷和环氧丙烷的共聚物。聚醚可以衍生自:
0wt%到60wt%的环氧丙烷和40wt%到100wt%的环氧乙烷,或
0wt%到50wt%的环氧丙烷和50wt%到100wt%的环氧乙烷,或
0wt%到30wt%的环氧丙烷和70wt%到100wt%的环氧乙烷,或
0wt%到20wt%的环氧丙烷和80wt%到100wt%的环氧乙烷,或
0wt%到15wt%的环氧丙烷和85wt%到100wt%的环氧乙烷。
聚醚胺可以从亨斯迈公司(Huntsman Corporation)以胺的形式商购获得。胺的具体实例是L-100(环氧丙烷与环氧乙烷的混合比率为3/19)、L-207(环氧丙烷与环氧乙烷的混合比率为10/33)、L-200(环氧丙烷与环氧乙烷的混合比率为4/41)和L-300(环氧丙烷与环氧乙烷的混合比率为8/58)。括号中的数字分别是环氧丙烷和环氧乙烷的近似重复单元数。
对于极性有机介质基分散体,聚醚可以衍生自:
0wt%到60wt%的环氧乙烷和40wt%到100wt%的环氧丙烷,或
0wt%到50wt%的环氧乙烷和50wt%到100wt%的环氧丙烷,或
0wt%到30wt%的环氧乙烷和70wt%到100wt%的环氧丙烷,或
0wt%到20wt%的环氧乙烷和80wt%到100wt%的环氧丙烷,或
0wt%到15wt%的环氧乙烷和85wt%到100wt%的环氧丙烷。
实施例2-具有聚醚链的芳香族酰胺功能分散剂
在实施例2中,使聚亚烷基二醇(甲基)丙烯酸酯与伯胺反应,然后与酸官能化的芳香族酸酐反应。伯胺反应物可以是含有环氧烷单元,如环氧乙烷、环氧丙烷、环氧丁烷和环氧苯乙烷的数均分子量为100到10000,更理想地400到2500的聚醚胺,或者伯胺可以是含有具有1到50个,更理想地1到20个碳原子并且含有一种或两种(更理想地仅一种)伯胺和至多一种或两种仲胺或其它含氮基团,如酰胺键的分子量较低的非聚合胺,如直链的、支链的、环状的并且甚至是芳香族的。理想地,伯胺反应物可以含有其它杂原子,如氧和氮(以及任选地硫),每个伯胺分子的氧、氮和任选地硫的量至多为4个杂原子。在一个优选实施例中,伯胺是聚醚胺,如先前讨论的聚醚胺。在另一个优选实施例中,伯胺是除了伯胺的氮以外没有杂原子的烷基胺。在另一个优选实施例中,伯胺是含有C1-20的氨基羧酸并且可以含有其它杂原子,如氧和氮(以及任选地硫)。在另一个优选实施例中,伯胺是含有C1-20的氨基醇并且可以含有其它杂原子,如氧和氮(以及任选地硫)。在另一个优选实施例中,伯胺是含有C1-20的芳香族胺并且可以含有其它杂原子,如氧和氮(以及任选地硫)。
实例是丁胺与聚(乙二醇)(甲基)丙烯酸酯Mn 1000反应,然后与酸官能化的芳香族酸酐反应。
实施例3-具有聚醚链的芳香族酰胺功能分散剂
在实施例3中,使聚亚烷基二醇(甲基)丙烯酸酯与聚醚胺反应,然后与酸官能化的芳香族酸酐反应。
实施例4-具有聚酯链的芳香族酰胺功能分散剂
在一个实施例中,本发明提供了一种聚合物,所述聚合物包括具有至少一个芳香族叔酰胺连接基团的聚合物链,所述芳香族叔酰胺连接基团与具有侧基酸官能团的芳香族基团以及聚醚基团和G基团连接,其中所述聚合物由式I表示。
在一个实施例中,本发明提供了一种聚合物,所述聚合物包括具有至少一个芳香族叔酰胺连接基团的聚合物链,所述芳香族叔酰胺连接基团与具有侧基羧酸官能团的芳香族基团以及聚醚基团和聚酯基团两者连接,其中所述聚合物由式I表示。
可用于使上述聚酯基团聚合的内酯的实例包含β-丙内酯、γ-丁内酯、任选的烷基取代的ε-己内酯和任选地烷基取代的δ-戊内酯。ε-己内酯和δ-戊内酯中的烷基取代基可以是C1-6烷基或C1-4烷基并且可以是直链或支链的。合适的内酯的实例是ε-己内酯和己内酯或戊内酯的7-甲基-、2-甲基-、3-甲基-、5-甲基-、6-甲基-、4-甲基、5-叔丁基-、4,4,6-三甲基-和4,6,6-三甲基-类似物。
酯化催化剂可以是本领域之前已知的任何酯化催化剂并且可以包含辛酸锡(II);钛酸四烷基酯,例如,钛酸四丁酯;有机酸的锌盐,例如,乙酸锌;脂肪族醇的锆盐,例如,异丙醇锆;甲苯磺酸;或强有机酸,如三氟乙酸或磷酸。
所述方法可以在由元素周期表(Periodic Table)的任何惰性气体但通常为氮气提供的惰性气氛中进行。所述方法可以在熔体中或在存在或不存在溶剂的情况下进行。溶剂可以是非极性溶剂(如芳香族或脂肪族化合物)、极性有机溶剂或水。溶剂在本领域中是众所周知的。
在一个实施例中,本发明的聚合物(通常由式I表示)可以通过包括以下的方法获得或可通过所述方法获得:步骤(1):使迈克尔受体,如(甲基)丙烯酸酯或官能化的(甲基)丙烯酸酯与亲核性聚合链,如聚醚胺中的氮原子反应,从而形成聚醚仲胺;步骤(2):使所述聚醚仲胺与酸官能化的芳香族二酸或酸酐,如三羧酸苯酸酐反应,以在所述芳香族酸与所述聚醚之间形成叔酰胺连接基团。
在以上实施例中,所述第一步骤可以在约0℃到150℃,更理想地约30℃到80℃的温度下进行,并且形成所述叔酰胺的所述第二反应步骤可以在约0℃到120℃,并且更优选地约30℃到80℃的温度下进行。
在一个实施例中,本发明的聚合物(通常由式I表示)可以通过包括以下的方法获得或可通过所述方法获得:步骤(1):使具有不饱和丙烯酸酯官能团的聚合丙烯酸酯大分子单体,如MPEG丙烯酸酯与亲核性的脂肪族胺反应,从而形成MPEG官能化的仲胺;和
步骤(2):使来自步骤(1)的所述MPEG官能化的仲胺与酸官能化的芳香族二酸或酸酐反应,如三羧酸苯酸酐,以由所述二酸或酸酐的酸基之一形成叔酰胺键,从而将所述MPEG与所述酸官能化的芳香族二酸(现在为酸/酰胺)连接,其中所述第一步骤,即迈克尔反应可以在约0℃到150℃,更理想地约30℃到80℃的温度下进行;形成所述叔酰胺的所述第二反应步骤是在约0℃到120℃,并且更理想地约30℃到80℃的酰胺化温度下进行的。
在一个实施例中,本发明提供了一种组合物,所述组合物包括颗粒状固体、水性介质或极性有机介质以及具有至少一个叔酰胺侧基的式I的分散剂,其中所述分散剂由以上定义的式I表示。所述组合物可以是漆浆、涂料(油漆)或油墨。
在一个实施例中,本发明提供了一种组合物,所述组合物包括颗粒状固体、水性介质或极性有机介质、根据式I的分散剂以及粘结剂。在一个实施例中,粘结剂可以是聚环氧化物、聚氨酯、聚酰胺、聚(甲基)丙烯酸酯、聚酯、纤维素或醇酸树脂。
在一个实施例中,本发明提供了一种组合物,所述组合物包括颗粒状固体、水性介质或极性有机介质以及具有至少一个叔酰胺连接基团的分散剂(其中所述分散剂由上式I表示)并且进一步包括粘结剂。在一个实施例中,粘结剂可以是纤维素(如硝化纤维素)、聚氨酯、聚(甲基)丙烯酸酯、聚酯或聚酰胺。
本发明的组合物中的本文公开的颗粒状固体可以是颜料或填料。在一个实施例中,颜料可以是有机颜料,在一个实施例中,颜料可以是无机颜料,并且在一个实施例中,颜料可以是炭黑。在本公开中,优选无机类型的颗粒或炭黑。
在一个实施例中,本发明提供了一种涂料(油漆)或油墨,所述涂料(油漆)或油墨包括颗粒状固体、水性介质或极性有机介质、成膜树脂和本文公开的本发明的分散剂。
在一个实施例中,本发明提供了一种涂料(油漆)或油墨,所述涂料(油漆)或油墨包括颗粒状固体、极性有机介质、成膜树脂和本文公开的本发明的分散剂。
当所述组合物是油墨时,所述油墨可以是喷墨油墨、柔印油墨、胶印油墨或凹印油墨。油墨可以是可辐射固化的油墨。
在一个实施例中,本发明提供了一种组合物,所述组合物包括由以上定义的式I表示的分散剂、无机颜料(和/或炭黑)和粘结剂。粘结剂可以选自由以下组成的组:纤维素、聚丙烯酸、聚酯、聚醚、聚氨酯、醇酸树脂和聚酰胺。所述组合物可以在用于印刷工艺,如柔性版印刷工艺的油墨或喷墨油墨,如可辐射固化、无压且按需喷墨(drop on demand)的油墨中使用。
本发明的分散剂可以以范围在本文公开的组合物的总重量的0.1wt%到79.6wt%、或0.5wt%到30wt%或1wt%到25wt%内的量存在于所述组合物中。
在一个实施例中,本发明提供了一种分散剂聚合物的用途,其中所述分散剂聚合物由上文定义的式I表示为本文公开的组合物中的分散剂。
在一个实施例中,本发明提供了一种由上文定义的式I表示的分散剂作为使用炭黑和无机颜料中的至少一种的油墨组合物中的分散剂的用途。所述油墨组合物可以表现出以下特性中的至少一种特性:粒度减小、粒度分布减小(通常减小到平均150nm或更小)、雾度降低、光泽度提高、喷射性增加(特别是当所述组合物为黑色时)和在环境储存和高温储存条件下稳定。
在不受理论约束的情况下,据信,芳香族酰胺侧基可以充当本发明的分散剂与颗粒状固体,如选自无机颜料和/或炭黑的颜料之间的锚定基团。
氨基羧酸(或氨基酸)可以是氨基-C2-20-亚烷(烯)基羧酸并且可以或可以不含有多于一个羧酸基并且可以或可以不含有多余一个氨基。氨基羧酸可以或可以不含有包含杂原子的其它基团,如羟基或硫醇基。亚烷(烯)基可以是直链或支链的。氨基羧酸的亚烷(烯)基含有不超过12个碳原子。具体的实例包含11-氨基十一酸、12-氨基十二酸、6-氨基己酸、4-氨基丁酸、天冬氨酸、谷氨酸、赖氨酸、天冬酰胺、谷氨酰胺、苏氨酸、丝氨酸、半胱氨酸、β-丙氨酸、甘氨酸和肌氨酸。可以使用氨基羧酸的混合物。
在具有4n+2个π电子的Q内定义的技术特征对于本领域的技术人员来说是熟知的休克尔规则(Hückel's rule)。通常,n可以等于2(即,π电子的数量为10)或3(即,π电子的数量为14)。在一个实施例中,n可以等于2。
通常,Q包括衍生自芳香族二或四羧酸或其酸酐或它们的混合物的一个或多个芳环(任选稠合的)。R1独立地为CO2H或SO3H,其中a可以为1到3。
R2可以是烷基或具有直链或支链烷基的任选取代的烷基。
由R2定义的烷基包含甲基、乙基、丙基、丁基、戊基、己基、庚基、2-乙基己基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基、二十碳烷基或它们的混合物。在一个实施例中,R2可以衍生自烷醇。
R3可以独立地为C1-50,更理想地C1-20任选取代的烃基,如烷基。
聚醚胺可以从亨斯迈公司以胺的形式商购获得。胺的具体实例是L-100(环氧丙烷与环氧乙烷的混合比率为3/19)、L-207(环氧丙烷与环氧乙烷的混合比率为10/32)、L-200(环氧丙烷与环氧乙烷的混合比率为3/41)和L-300(环氧丙烷与环氧乙烷的混合比率为8/58)。括号中的数字分别是环氧丙烷和环氧乙烷的近似重复单元数。
在式I中,整数x为使得R2-O-(Y)x-T-N链的数均分子量可以为100到10,000、或100到5,000、或300到3,000或400到2,500。
上文的反应是如何制备聚醚侧链,其中上文描述的方法中的环氧乙烷可以在100℃到200℃的温度下在存在碱的情况下进行,所述碱如氢氧化钾或氢氧化钠。
在式I和II、III、IV和IV以及其子集中,可以形成用于富水有机介质的分散剂,其中聚醚含有至少60wt%到100wt%的环氧乙烷,或者实施例其中形成用于极性有机介质的分散剂,其中聚醚含有至少40wt%到60wt%的环氧乙烷。
通常,对于水性介质分散剂,按(Y)x的重量计,式I的(Y)x含有60wt%到100wt%、70wt%到100wt%、或80wt%到100wt%或100wt%的环氧乙烷;0wt%到40wt%、或0wt%到30wt%、或0wt%到20wt%或0wt%的环氧丙烷。
本发明的聚合物可以具有多种连接的由式IVa、IVb表示的聚合物链类型。
式I或其任何子式的聚合物链的数均分子量可以为200到10,000、或300到5,000、或500到3,000或600到2,500。通常,式I或其任何子式的聚合物链的数均分子量可以为1,000到2,500。
工业应用
存在于组合物中的颗粒状固体可以为任何无机或有机固体材料,其在相关温度下基本上不可溶于有机介质和/或不溶于水,并且期望使其以细碎形式稳定于组合物中。颗粒状固体可以呈粒状材料、纤维、薄片的形式或者呈粉末,通常是吹制粉末的形式。在一个实施例中,颗粒状固体是颜料。
通过光散射测量,颗粒状固体(通常是颜料或填料)的平均粒度(直径)可以为10纳米到10微米、或10纳米到1、2、3或5微米或20纳米到1、2、3或5微米。
合适的固体的实例为:用于油漆和塑料材料的颜料、增量剂、填料、发泡剂和阻燃剂;染料,尤其是分散染料;光学增亮剂和纺织助剂;用于油墨、墨粉的颜料;用于油基和反相乳液钻井泥浆的固体;干洗液中的灰尘和固体颗粒;金属;用于陶瓷、压电陶瓷印刷、耐火材料、研磨剂、铸造厂、电容器、燃料电池、铁磁流体、导电油墨、磁记录介质、水处理和烃土壤修复的颗粒状陶瓷材料和磁性材料;有机和无机纳米分散固体;用于电池中的电极的金属、金属氧化物和碳;用于复合材料的纤维,如木材、纸张、玻璃、钢、碳和硼;以及在有机介质中用作分散体的杀生物剂、农药和药物。
在一个实施例中,固体是来自例如在《颜色索引第三版(Third Edition of theColor Index)》(1971)和其后续修订版和补充版中在标题为“颜料(Pigments)”的章节中描述的公认颜料类别中的任何颜料类别的有机颜料。有机颜料的实例是来自以下的有机颜料:偶氮、双偶氮、三偶氮、缩合偶氮、偶氮色淀、萘酚颜料、蒽嵌蒽醌、蒽素嘧啶、蒽醌、苯并咪唑酮、咔唑、吡咯并吡咯二酮、黄烷士酮、靛蓝颜料、靛蒽醌、异蒽酮紫、异靛蒽酮、异吲哚啉酮、异吲哚啉、异蒽酮紫、金属络合物颜料、嗪、二萘嵌苯、环酮(perinone)、皮蒽酮、吡唑并喹唑酮、喹吖啶酮、喹啉黄(quinophthalone)、硫靛、三芳基阳碳(triarylcarbonium)颜料、三苯二噁嗪(triphendioxazine)、氧杂蒽和酞菁系列,特别是铜酞菁和其核卤代衍生物以及酸性、碱性和媒染染料色淀。尽管严格地说炭黑是无机的,但就分散性能而言,其更像有机颜料。在一个实施例中,有机颜料为酞菁,尤其是铜酞菁、单偶氮、双偶氮、靛蒽醌、蒽缔蒽酮、喹吖啶酮、吡咯并吡咯二酮、二萘嵌苯和炭黑。
无机颜料的实例包含金属氧化物,如二氧化钛、金红石二氧化钛和表面涂覆的二氧化钛、不同颜色(如黄色和黑色)的氧化钛、不同颜色(如黄色、红色、棕色和黑色)的氧化铁、氧化锌、氧化锆、氧化铝、含氧金属化合物,如钒酸铋、铝酸钴、锡酸钴、锌酸钴、铬酸锌和锰、镍、钛、铬、锑、镁、钴、铁或铝中的两种或更多种的混合金属氧化物、普鲁士蓝(Prussianblue)、朱砂(vermillion)、群青(ultramarine)、磷酸锌、硫化锌、钙和锌的钼酸盐和铬酸盐、金属效果颜料,如薄铝片、铜和铜/锌合金、珠光薄片,如碳酸铅和氯氧化铋。
无机固体包含增量剂和填料,如研磨和沉淀的碳酸钙、硫酸钙、氧化钙、草酸钙、磷酸钙、膦酸钙、硫酸钡、碳酸钡、氧化镁、氢氧化镁、天然氢氧化镁或水镁石、沉淀的氢氧化镁、碳酸镁、白云石、氢氧化铝、氢过氧化铝或勃姆石、硅酸钙和硅酸镁、铝硅酸盐,包含纳米粘土、高岭土、蒙脱石,包含膨润土、锂蒙脱石和皂石、球粘土,包含天然、合成和可膨胀的球粘土、云母、滑石,包含白云母、金云母、锂云母和绿泥石、白垩、合成和沉淀的二氧化硅、气相二氧化硅、金属纤维和粉末、锌、铝、玻璃纤维、耐火纤维、炭黑,包含单壁和多壁碳纳米管、增强性和非增强性炭黑、石墨、富勒烯(Buckminsterfullerene)、沥青质、石墨烯、金刚石、氧化铝、石英、珍珠岩、伟晶岩、硅胶、木粉、木薄片,包含软木和硬木、锯末、粉状纸/纤维、纤维素纤维,如洋麻、大麻、剑麻、亚麻、棉花、棉籽绒、黄麻、苎麻、稻壳或果壳、酒椰、香蒲芦苇、椰子纤维、椰壳纤维、油棕纤维、木棉、香蕉叶、卡罗(caro)、卡罗阿(curaua)、龙舌兰纤维叶(henequen leaf)、亚麻叶(harakeke leaf)、蕉麻、甘蔗渣、秸秆、竹条、小麦粉、MDF等、蛭石、沸石、水滑石、来自发电厂的粉煤灰、焚化的污水污泥灰、火山灰(pozzolane)、高炉矿渣、石棉、温石棉、直闪石、青石棉、硅灰石、凹凸棒石等、颗粒状陶瓷材料,如氧化铝、氧化锆、二氧化钛、二氧化铈、氮化硅、氮化铝、氮化硼、碳化硅、碳化硼、混合硅-铝氮化物和金属钛酸盐;颗粒状磁性材料,如过渡金属(通常为铁和铬)的磁性氧化物,例如,γ-Fe2O3、Fe3O4和钴掺杂的氧化铁、铁氧体,例如,钡铁氧体;以及金属颗粒,例如金属铝、铁、镍、钴、铜、银、金、钯和铂以及其合金。
其它可用的固体材料包含阻燃剂,如五溴二苯醚、八溴二苯醚、十溴二苯醚、六溴环十二烷、聚磷酸铵、三聚氰胺、氰尿酸三聚氰胺、氧化锑和硼酸盐;杀生物剂或工业微生物制剂,如《柯克-奥斯特默化学技术百科全书(Kirk-Othmer's Encyclopedia ofChemicalTechnology)》第13卷,1981,第3版中题为“工业微生物制剂(IndustrialMicrobial Agents)”的章节的表2、3、4、5、6、7、8和9中提及的杀生物剂或工业微生物制剂、以及农药,如杀真菌剂、粉唑醇(flutriafen)、多菌灵(carbendazim)、百菌清(chlorothalonil)和代森锰锌(mancozeb)。
在一个实施例中,极性液体介质是水,但是可以含有至多50重量%(按水和极性溶剂的总重量计)的水溶性极性助溶剂。可以充当极性溶剂的这种助溶剂的实例是醇,如乙醇、异丙醇、正丙醇或正丁醇;或水混溶性有机溶剂,如乙二醇或二甘醇的单或二烷基醚;或极性溶剂,如二甘醇、甘油、2-吡咯烷酮、N-甲基吡咯烷酮、环己醇、己内酯、己内酰胺、戊烷-1,5-二醇、2-(丁氧基乙氧基)乙醇和硫二甘醇以及乙二醇;包含任何先前指定的醇或溶剂的混合物。相对于有机液体,术语“极性”意味着有机液体能够形成中强键,如Crowley等人在《油漆技术杂志(Journal of Paint Technology)》第38卷,1966,第269页中在题为“三维溶解度方法(A Three Dimensional Approach to Solubility)”的文章中所述。极性有机液体的介电常数通常为5或以上,如以上提及的文章中所定义。非极性液体的介电常数通常小于5。
漆浆或分散体可用于通过与另外量的一种或多种水相容性树脂和/或水以及通常掺入到水性油漆和油墨中的其它成分,如防腐剂、稳定剂、消泡剂、水混溶性助溶剂和聚结剂混合以制备水性油漆(涂料)和油墨。
水相容性树脂可以是在水性涂料行业中使用的任何水溶性或水不溶性聚合物。在乳胶或水可稀释涂料中通常用作主要成膜粘结剂树脂的聚合物的实例是丙烯酸、乙烯基酯、聚氨酯、聚酯、环氧树脂和醇酸树脂。
在一个实施例中,本发明的组合物中存在的有机介质是塑料材料,而在另一实施例中是有机液体。有机液体可以是极性有机液体。相对于有机液体,术语“极性”意味着有机液体能够形成中强键,如Crowley等人在《油漆技术杂志》第38卷,1966,第269页中在题为“三维溶解度方法”的文章中所述。这种有机液体的氢键数通常为5或以上,如以上提及的文章中所定义。
合适的极性有机液体的实例为胺、醚,尤其是低级烷基醚、有机酸、酯、酮、二醇、二醇醚、二醇酯、醇和酰胺。Ibert Mellan在题为“兼容性和溶解度(Compatibility andSolubility)”的书(由诺伊斯发展公司(Noyes Development Corporation)于1968年出版)中在第39-40页的表2.14中给出了这种中强氢键液体的多个具体实例,并且这些液体全都落入本文使用的术语极性有机液体的范围内。
在一个实施例中,极性有机液体为二烷基酮、烷烃羧酸的烷基酯和烷醇,尤其是含有至多并且包含总共6个碳原子的这种液体。作为极性有机液体的实例,包含二烷基和环烷基酮,如丙酮、甲乙酮、二乙基酮、二异丙基酮、甲基异丁基酮、二异丁基酮、甲基异戊基酮、甲基正戊基酮和环己酮;烷基酯,如乙酸甲酯、乙酸乙酯、乙酸异丙酯、乙酸丁酯、甲酸乙酯、丙酸甲酯、乙酸甲氧基丙酯和丁酸乙酯;乙二醇和乙二醇酯和醚,如乙二醇、2-乙氧基乙醇、3-甲氧基丙基丙醇、3-乙氧基丙基丙醇、乙酸2-丁氧基乙酯、乙酸3-甲氧基丙酯、乙酸3-乙氧基丙酯和乙酸2-乙氧基乙酯;链烯醇,如甲醇、乙醇、正丙醇、异丙醇、正丁醇和异丁醇(也称为2-甲基丙醇)、松油醇和二烷基和环状醚,如乙醚和四氢呋喃。在一个实施例中,溶剂为烷醇、烷烃羧酸和烷烃羧酸的酯。在一个实施例中,本发明适用于基本上不可溶于水性介质的有机液体。此外,本领域的技术人员将认识到,只要整体有机液体基本上不溶于水性介质,则有机液体中可以存在少量的水性介质(如乙二醇、乙二醇醚、乙二醇酯和醇)。
可用作极性有机液体的有机液体的实例是成膜树脂,如适合于制备用于各种应用的油墨、油漆和碎屑,如油漆和油墨。这种树脂的实例包含聚酰胺,如VersamidTM和WolfamidTM以及纤维素醚,如乙基纤维素和乙基羟乙基纤维素、硝化纤维素和乙酸丁酸纤维素树脂,包含它们的混合物。油漆树脂的实例包含短油醇酸树脂/三聚氰胺-甲醛、聚酯/三聚氰胺-甲醛、热固性丙烯酸/三聚氰胺-甲醛、长油醇酸树脂、中油醇酸树脂、短油醇酸树脂、聚醚多元醇和多介质树脂,如丙烯酸和脲/醛。
有机液体可以为多元醇,即具有两个或更多个羟基的有机液体。在一个实施例中,多元醇包含α-Ω二醇或α-Ω二醇乙氧基化物。
在一个实施例中,按总有机液体计,有机液体包括至少0.1重量%或1重量%或更多的极性有机液体。有机液体任选地进一步包括水。在一个实施例中,有机液体不含水(通常少于2wt%的水、或少于1wt%的水、或少于0.5wt%的水或少于0.1wt%)。
塑料材料可以是热固性树脂。可用于本发明的热固性树脂包含在加热、催化或经受紫外线、激光、红外线、阳离子、电子束或微波辐射时发生化学反应并变得相对不熔的树脂。热固性树脂中的典型反应包含不饱和双键的氧化、涉及环氧树脂/胺、环氧树脂/羰基、环氧树脂/羟基的反应、环氧树脂与路易斯酸(Lewis acid)或路易斯碱(Lewis base)、聚异氰酸酯/羟基、氨基树脂/羟基部分的反应、自由基反应或聚丙烯酸酯、环氧树脂和乙烯基醚的阳离子聚合以及硅烷醇的缩合。不饱和树脂的实例包含通过一种或多种二酸或酸酐与一种或多种二醇反应制得的聚酯树脂。这种树脂通常以与反应性单体(如苯乙烯或乙烯基甲苯)的混合物形式提供并且通常被称为邻苯二甲酸树脂和间苯二甲酸树脂。另外的实例包含在聚酯链中使用二环戊二烯(DCPD)作为共反应剂的树脂。另外的实例还包含双酚A二缩水甘油醚与不饱和羧酸如甲基丙烯酸的反应产物,随后以在苯乙烯中的溶液形式提供,通常称为乙烯基酯树脂。
在一个实施例中,热固性复合材料或热固性塑料可以是聚酯、聚乙酸乙烯酯、苯乙烯中的聚酯树脂、聚苯乙烯或它们的混合物。
具有羟基官能团的聚合物(通常是多元醇)广泛用于热固性体系中,以与氨基树脂或聚异氰酸酯交联。多元醇包含丙烯酸多元醇、醇酸多元醇、聚酯多元醇、聚醚多元醇和聚氨酯多元醇。典型的氨基树脂包含三聚氰胺甲醛树脂、苯代三聚氰胺甲醛树脂、脲甲醛树脂和甘脲甲醛树脂。聚异氰酸酯是具有两个或更多个异氰酸酯基团的树脂,包含单体脂肪族二异氰酸酯、单体芳香族二异氰酸酯以及其聚合物。典型的脂肪族二异氰酸酯包含六亚甲基二异氰酸酯、异佛尔酮二异氰酸酯和氢化的二苯甲烷二异氰酸酯。典型的芳香族异氰酸酯包含甲苯二异氰酸酯和二苯基甲烷二异氰酸酯。
如果需要,本发明的组合物可以含有其它成分,例如树脂(其中这些树脂尚未构成有机介质)、粘结剂、助溶剂、交联剂、流化剂、润湿剂、抗沉淀剂、塑化剂、表面活性剂、除本发明的化合物以外的分散剂、保湿剂、消泡剂、抗缩孔剂、流变改性剂、热稳定剂、光稳定剂、UV吸收剂、抗氧化剂、调平剂、光泽度调节剂、杀生物剂和防腐剂。
如果需要,含有热固性塑料材料的组合物可以含有其它成分,例如,除本发明的化合物外的分散剂、发泡剂、阻燃剂、加工助剂、表面活性剂、热稳定剂、UV吸收剂、抗氧化剂、芳香剂、脱模助剂、抗静电剂、抗微生物剂、杀生物剂、偶联剂、润滑剂(外部和内部)、抗冲击改性剂、助滑剂、脱气剂和降粘剂。
组合物通常含有1重量%到95重量%的颗粒状固体,精确的量取决于固体的性质,并且所述量取决于固体的性质以及固体和极性有机液体的相对密度。例如,在一个实施例中,按组合物的总重量计,固体为有机材料,如有机颜料的组合物含有15重量%到60重量%的固体,而在一个实施例中,固体为无机材料,如无机颜料、填料或增量剂的组合物含有40重量%到90重量%的固体。
可以通过已知用于制备分散体的任何常规方法来制备含有有机液体的组合物。因此,固体、有机介质和分散剂可以任何顺序混合,然后例如通过高速混合、球磨、篮式碾磨、珠粒碾磨、砾石碾磨、砂磨、摩机研磨、两辊或三辊碾磨、塑料碾磨对混合物进行机械处理以将固体的颗粒减小到合适的大小,直到形成分散体。可替代地,可以将固体单独地或与有机介质或分散剂混合处理以减小其粒度,然后加入一种或多种其它成分,并搅动混合物以提供组合物。组合物还可以通过将干燥固体与分散剂一起研磨或碾磨,然后添加液体介质或在颜料冲洗过程中将固体与分散剂在液体介质中混合来制备。
含有塑料材料的组合物可以通过已知用于制备热塑性化合物的任何常规方法制备。因此,固体、热塑性聚合物和分散剂可以任何顺序混合,然后例如通过班伯里混合(Banbury mixing)、带式共混、双螺杆挤出、双辊碾磨、布斯混炼机(Buss co-kneader)中的混配或类似设备对混合物进行机械处理以将固体的颗粒减小到合适的大小。
本发明的组合物特别适合于液体分散体。在一个实施例中,这种分散组合物包括:
(a)0.5份到80份的颗粒状固体;
(b)0.1份到79.6份的式I的聚合物;以及
(c)19.9份到99.4份的有机液体和/或水;其中所有相对份数均按重量计,并且量(a)+(b)+(c)=100。
在一个实施例中,组分a)包括0.5份到30份的颜料,并且这种分散体用作(液体)油墨、涂料(油漆)和漆浆。
如果需要包括干燥形式的颗粒状固体和式I的分散剂的组合物,则有机液体通常是挥发性的,使得可以通过简单的分离手段,如蒸发将其容易地从颗粒状固体中去除。在一个实施例中,组合物包括有机液体。
如果干燥组合物基本上由式I的分散剂和颗粒状固体组成,则按颗粒状固体的重量计,其通常含有至少0.2%、至少0.5%或至少1.0%的式I的分散剂。在一个实施例中,按颗粒状固体的重量计,干燥组合物含有不超过100重量%、不超过50重量%、不超过20重量%或不超过10重量%的式I的分散剂。
如本文之前所公开的,本发明的组合物适合于制备漆浆,其中颗粒状固体在式I的化合物存在下在有机液体中碾磨。
因此,根据本发明的仍另外一方面,提供了一种漆浆,所述漆浆包括颗粒状固体、有机液体和式I的聚合物。
通常,按漆浆的总重量计,漆浆含有20重量%到70重量%的颗粒状固体。在一个实施例中,颗粒状固体不少于漆浆的10重量%或不少于20重量%。此类漆浆可以任选地含有在碾磨之前或碾磨之后添加的粘结剂。
在一个实施例中,粘结剂是能够在有机液体挥发时粘结组合物的聚合材料。
粘结剂是包含天然和合成材料的聚合材料。在一个实施例中,粘结剂包含聚(甲基)丙烯酸酯、聚苯乙烯、聚酯、聚氨酯、醇酸树脂、多糖,如纤维素、硝化纤维素和天然蛋白质,如酪蛋白。粘结剂可以为硝化纤维素。在一个实施例中,以颗粒状固体的量计,粘结剂以大于100%、大于200%、大于300%或大于400%的量存在于组合物中。
漆浆中的任选粘结剂的量可在宽限值内变化,但通常不少于漆浆的连续/液相的10重量%,并且通常不少于20重量%。在一个实施例中,粘结剂的量不超过漆浆的连续/液相的50重量%或不超过40重量%。
漆浆中的分散剂的量取决于颗粒状固体的量,但通常为漆浆的0.5重量%到5重量%。
由本发明的组合物制备的分散体和漆浆特别适合用于非水性和无溶剂调配物,其中可能量固化的系统(紫外线、激光、红外线、阳离子、电子束、微波)与存在于调配物中的单体、低聚物等或组合物一起采用。其特别适用于涂料,如油漆、清漆、油墨、其它涂覆材料和塑料。合适的实例包含其在以下中使用:低、中和高固体油漆、一般工业油漆,包含烘烤、双组分和金属涂覆油漆,如线圈和罐头涂料、粉末涂料、可UV固化的涂料、木材清漆;油墨,如弹性印刷油墨、凹版印刷油墨、胶印油墨、平版印刷油墨、凸版印刷(letterpress或relief)油墨、丝网印刷油墨和用于包装印刷的印刷油墨、无压油墨,如喷墨油墨,包含连续喷墨和按需喷墨,其包含热、压电和静电按需喷墨、相变油墨和热熔蜡油墨、用于喷墨打印机的油墨和印刷清漆,如复印清漆;多元醇和增塑溶胶分散体;非水性陶瓷工艺,特别是流延成型、凝胶注模成型、刮刀法、挤压和注塑成型工艺,另外一个实例是制备在用于等静压制的干陶瓷粉末中使用;复合材料,如片状模塑和块状模塑化合物、树脂传递模塑、挤压成型、手糊和喷涂工艺、匹配的合模模塑;建筑材料,如铸造树脂、化妆品、个人护理,如指甲油、防晒霜、粘合剂,如液体调色剂、塑料材料和电子材料,如用于包含有机发光二极管(OLED)装置的显示器、液晶显示器和电泳显示器中的彩色滤光片系统的涂料调配物、玻璃涂料,包含光纤涂料、反射涂料或抗反射涂料、导电和磁性油墨和涂料。其可用于对颜料和填料进行表面改性以改善上述应用中使用的干粉的分散性。涂覆材料的另外实例在Bodo Muller,UlrichPoth,Lackformulierungund Lackrezeptur,Lehrbuch fr Ausbildung und Praxis,Vincentz Verlag,汉诺威(Hanover)(2003)和P.G.Garrat,Strahlenhartung,VincentzVerlag,汉诺威(1996)中给出。在E.W.Flick,《印刷油墨和叠印清漆调配物-最新进展(Printing Ink and Overprint Varnish Formulations-Recent Developments)》,新泽西州帕克里奇诺伊斯出版社(Noyes Publications,Park Ridge NJ),(1990)和后续版本中给出了印刷油墨调配物的实例。
由本发明的组合物制成的分散体和漆浆还可用于接触式和非接触式(按需喷墨)水性印刷工艺,如水性柔印、水性喷墨、水性UV喷墨。
在一个实施例中,本发明的组合物进一步包含一种或多种另外的已知分散剂。
以下实例提供了对本发明的说明。这些实例为非穷尽性的并且不旨在限制本发明的范围。
实例
比较实例1(CE1)-聚醚胺与1,2,4-苯三羧酸酐反应。
除了L207代替XJT-507之外,根据美国专利公开2005/0120911中的实例1制备分散剂。将1,2,4-苯三羧酸酐(14.4份)和聚醚胺(150.0份,L207,MW:2000,前亨斯迈)在氮气气氛下在120℃下搅拌1小时,然后在160℃下搅拌4小时,直到通过IR光谱法测定未剩下酸酐为止。最终产物的酸值为27.4mg KOH/g,并且在1714.9cm-1处存在酰亚胺峰。
实例1(EX1)-聚醚胺与丙烯酸2-羧乙酯,然后与1,2,4-苯三羧酸酐反应。
将聚醚胺(1023份,L207,MW:2000,前亨斯迈)和3,5-二-叔-4-丁基羟基甲苯(0.8份)在空气气氛下在50℃下搅拌。经25分钟向此混合物中逐滴添加丙烯酸2-羧乙酯(73.66份),并在50℃下保持1小时,然后在80℃下保持3小时,直到通过1H NMR光谱测定不存在乙烯基峰为止。然后,将温度降至55℃,之后在氮气气氛下添加1,2,4-苯三羧酸酐(98.12份)。搅拌反应混合物,直到酸酐完全溶解,并且然后将其再加热9小时,直到通过IR光谱法测定未剩下酸酐为止。最终产物的酸值为77mg KOH/g,并且IR光谱法显示在1638cm-1处存在叔酰胺羰基峰。
分散测试1–制备钛白色颜料分散体。
通过将分散剂CE1和EX1(0.68份)溶于水(10.43份)中来制备分散体。向所述分散体中添加消泡剂(0.14份024,阿尔塔纳集团(Altana Group)前毕克化学公司(BYK-Chemie))、3mm玻璃珠(120份)和白色颜料(33.75份2360,前克罗诺斯公司(Kronos)),并且将内容物在Scandex振荡器上研磨1小时。使用EX1产生的分散体产生了液体漆浆,而CE1产生了凝胶。
总体而言,结果表明,本发明的聚合物提供以下中的至少一种:提高增加颗粒状固体负荷,形成改进的分散体,具有提高的亮度以及在水性介质中产生粘度降低的组合物。
如下所述,已经通过将某一聚苯乙烯标准物用于所有聚合物链使用如凝胶渗透色谱法(GPC)分析等已知方法测定了本发明的聚合物的数均分子量。
比较实例2(CE2)-聚醚胺与1,2,4-苯三羧酸酐反应。
除了L100代替XJT-507之外,根据美国专利公开2005/0120911中的实例1制备分散剂。将1,2,4-苯三羧酸酐(11.85份)和聚醚胺(64.77份,L100,MW:1000,前亨斯迈)在氮气气氛下在110℃下搅拌1小时,然后在170℃下搅拌5小时,直到通过IR光谱法测定未剩下酸酐为止。最终产物的酸值为48.16mg KOH/g,并且在1713cm-1处存在酰亚胺峰。
实例2(EX-2)-聚醚胺与丙烯酸,然后与1,2,4-苯三羧酸酐反应。
将聚醚胺(85.91份,L207,MW:2000,前亨斯迈)和吩噻嗪(0.026份)在空气气氛下在50℃下搅拌。向此混合物中添加丙烯酸(3.07份),将反应温度升高到80℃,并将混合物搅拌5.5小时,直到通过1H NMR光谱法测定不存在乙烯基峰为止。然后,将温度降至50℃,之后在氮气气氛下添加1,2,4-苯三羧酸酐(8.19份)。将反应混合物搅拌24小时,直到酸酐溶解,并且通过IR光谱法测定未剩下酸酐峰为止。最终产物的酸值为74.40mgKOH/g,并且IR光谱法显示在1637cm-1处存在叔酰胺羰基峰。
实例3(Ex3)-聚醚胺与丙烯酸2-羧乙酯,然后与1,2,4-苯三羧酸酐反应。
将聚醚胺(212.93份,L100,MW:1000,前亨斯迈)和3,5-二-叔-4-丁基羟基甲苯(0.84份)在空气气氛下在50℃下搅拌。经50分钟向此混合物中逐滴添加丙烯酸2-羧乙酯(28.85份),并在50℃下保持30分钟,然后在80℃下保持3小时,直到通过1H NMR光谱法测定不存在乙烯基峰为止。然后,将温度降至50℃,之后在氮气气氛下添加1,2,4-苯三羧酸酐(39.11份)。搅拌反应混合物,直到酸酐完全溶解,并且然后将其再加热10小时,直到通过IR光谱法测定未剩下酸酐峰为止。最终产物的酸值为117.71mg KOH/g,并且IR光谱法显示在1633cm-1处存在叔酰胺羰基峰。
实例4(Ex4)-聚醚胺与1,2-环氧基-3-苯氧基丙烷,然后与1,2,4-苯三羧酸酐反应。
将聚醚胺(101.64份,L100,MW:1000,前亨斯迈)和3,5-二-叔-4-丁基羟基甲苯(0.36份)在空气气氛下在50℃下搅拌。经10分钟向此混合物中逐滴添加1,2-环氧基-3-苯氧基丙烷(15.17份),并在50℃下保持搅拌30分钟。将反应混合物在50℃下再搅拌18小时,直到通过IR或1H NMR光谱法测定不存在环氧化物峰为止。此时,在氮气气氛下添加1,2,4-苯三羧酸酐(19.47份)。搅拌反应混合物,直到酸酐完全溶解,并且然后再加热10小时,直到通过IR光谱法测定未剩下酸酐为止。最终产物的酸值为81.79mg KOH/g,并且IR光谱法显示在1665cm-1处存在叔酰胺羰基峰。
分散测试2–制备钛白色颜料分散体水溶液。
通过将分散剂,即比较实例(CE-1和CE-2)和实例(EX1-4)(0.15份)溶解于水(3.32份)中来制备分散体。向所述分散体中添加(0.03份024,阿尔塔纳集团前毕克化学公司)、3mm玻璃珠(17份)和白色颜料(6.50份2360,前克罗诺斯公司),并且将内容物在水平振荡器上研磨16小时。然后,评估所得分散体的流动性。
表1–分散测试2的颜料分散结果
分散测试3–制备含钛白色颜料分散体的乙酸1-甲氧基-2-丙酯。
通过将分散剂,即比较实例(CE-1和CE-2)和实例(EX1-3)(0.15份)溶解于乙酸1-甲氧基-2-丙酯(2.35份)中来制备分散体。向所述分散体中添加3mm玻璃珠(17份)、白色颜料(7.50份2360,前克罗诺斯公司),并且将内容物在水平振荡器上研磨16小时。通过Microtrac DLS Nano-flex粒度分析仪测定所得分散体的粒度(D50和D90)。
表2–分散测试3的颜料分散结果
分散剂 | D50/nm | D90/nm |
实例1(EX-1) | 232.9 | 301.0 |
实例2(EX-2) | 228.9 | 316.0 |
比较实例1(CE-1) | 522.0 | 669.0 |
实例3(EX-3) | 235.2 | 280.1 |
比较实例2(CE-2) | 845.0 | 1206.0 |
以上提及的每个文件都通过引用并入本文。除非另外指示,否则本文提及的每种化学物质或组合物都应解释为可以含有异构体、副产物、衍生物的商业级材料以及通常理解为以商业级形式存在的其它这种材料。然而,除非另外指示,否则每种化学组分的量不包含通常可以存在于商品材料中的任何溶剂或稀释油。应当理解,本文所述的上下限的量、范围和比例限制可以独立地组合。类似地,本发明的每种要素的范围和量可与任一其它要素的范围或量一起使用。
尽管已经针对本发明的优选实施例对本发明进行了说明,但是应当理解,对所属领域的技术人员而言,在阅读说明书后,其各种修改将变得显而易见。因此,应当理解,本文公开的发明旨在覆盖落入所附权利要求的范围内的这种修改。
Claims (26)
1.一种分散剂或其盐,所述分散剂或其盐包括具有以下结构的分散剂聚合物:
式I
R1独立地为CO2H或SO3H,其中a为1到2或3;
R2为H或C1-50任选取代的烃基或C1-50任选取代的烃羰基;
其中T为-C(O)-CH(R4)CH2或C1-5烃基链;
当G为C1-50烃基时,T为-C(O)-CH(R4)CH2;
当G为丙烯酸酯的在迈克尔加成反应中与氮反应的残基或通过开环环氧聚合打开的环氧化物时,T为C1-5烃基链;
R4为H或Me;
G为任选地被杂原子取代的表示为醚、酯、醛、酮、酰胺、尿烷、醇或羧酸基的C1-50烃基,或任选取代的(甲基)丙烯酸烷基酯或(甲基)丙烯酰胺的残基,或下式表示的环氧化物的开环产物:
其中R6在每次出现时可以单独地为H或CH3或C2H5或以下基团之一:
其中D为C1-5烷基、CN、OH、NO2、NH2、卤素、CO2H、SO3H或OCH3;p为0到4;
R3为直链或支链的C1-50烷基;
Y在每个重复单元中独立地为C2-4亚烷基氧基;
Q为包括一个或多个芳环的亚烃基,所述一个或多个芳环任选地被R1取代,如果存在两个芳环则环是稠合的,其中与Q连接的羧酸基与Q中的所述芳环的碳原子相连接,其中:Q包括萘,或Q包括联苯,或Q包括苯基;并且
其中所述式中的任何酸的氢可以被金属、胺或铵阳离子替代使所述分散剂呈盐的形式;x为2到90。
2.根据权利要求1所述的分散剂或其盐,其中Q包括衍生自酸官能化的1,2-萘酸酰胺、酸官能化的2,3-萘酸酰胺或酸官能化的1,8-萘酸酰胺或它们的混合物的萘。
3.根据权利要求1所述的分散剂或其盐,其中D为CH3。
4.根据权利要求1所述的分散剂或其盐,其中杂原子为O或氮。
5.根据权利要求1或2所述的分散剂或其盐,其是通过包括以下的方法获得的或可通过所述方法获得:
步骤(1):使迈克尔受体与亲核性聚合链中的氮原子反应,从而形成聚醚官能化的仲胺;以及
步骤(2):使所述聚醚官能化的仲胺与酸官能化的芳香族二酸或其酸酐反应,以在所述芳香族二酸与所述聚醚之间形成叔酰胺连接基团。
7.根据权利要求5所述的分散剂或其盐,其中所述第一步骤是在0℃到150℃的温度下进行的,并且形成所述叔酰胺的所述第二反应步骤是在50℃到120℃的温度下进行的。
8.根据权利要求1或2所述的分散剂或其盐,其是通过包括以下的方法获得的或可通过所述方法获得:
步骤(1):使具有不饱和丙烯酸酯官能团的(甲基)丙烯酸酯或官能化的(甲基)丙烯酸酯单体与亲核性的脂肪族胺反应,从而形成MPEG官能化的仲胺;以及
步骤(2):使来自步骤(1)的所述MPEG官能化的仲胺与酸官能化的芳香族二酸或其酸酐反应,以由所述二酸或其酸酐的酸基之一形成叔酰胺键,从而将所述MPEG与所述芳香族二酸连接,其中所述第一步骤可以在0℃到150℃的温度下进行;形成所述叔酰胺的所述第二反应步骤是在0℃到120℃的酰胺化温度下进行的。
9.根据权利要求1或2所述的分散剂或其盐,其是通过包括以下的方法获得的或可通过所述方法获得:
步骤(1):使丙烯酸羟酯与亲核性的脂肪族胺反应,从而形成脂肪族仲胺;
步骤(2):使所述脂肪族仲胺与酸官能化的芳香族二酸或四酸或其酸酐反应,从而形成叔酰胺;以及
步骤(3):使所述叔酰胺的羟基与环氧化物或环状酯反应,其中所述环状酯任选地为己内酯,和/或使所述环氧化物或环状酯聚合以形成聚合性的聚醚链或聚酯链,其中所述第一步骤可以在0℃到150℃的温度下进行;形成叔酰胺的所述第二反应步骤是在50℃到120℃的温度下进行的;以及使所述环氧化物或环状酯聚合的所述第三步骤是在100℃到200℃的温度下进行的。
12.根据权利要求11所述的分散剂或其盐,其中D为CH3。
15.根据权利要求14所述的分散剂或其盐,其中D为CH3。
16.一种组合物,其包括颗粒状固体、水性介质或极性有机溶剂介质以及至少具有的聚合物链,其中所述聚合物由权利要求1到15中任一项的聚合物表示。
17.根据权利要求16所述的组合物,其中所述介质包括水性介质。
18.根据权利要求16所述的组合物,其中所述介质包括极性有机介质。
19.根据权利要求16、17或18所述的组合物,其中所述组合物是漆浆或油墨。
20.根据权利要求16、17或18所述的组合物,其中所述组合物是油漆。
21.根据权利要求16到18中任一项所述的组合物,其中所述颗粒状固体是颜料或填料。
22.根据权利要求19所述的组合物,其中所述颗粒状固体是颜料或填料。
23.根据权利要求16到18中任一项所述的组合物,其进一步包括粘结剂。
24.根据权利要求22所述的组合物,其进一步包括粘结剂。
25.根据权利要求16到18中任一项所述的组合物,其中按组合物总重量计,分散剂以0.1wt%到79.6wt%的量存在。
26.根据权利要求24所述的组合物,其中按组合物总重量计,分散剂以0.1wt%到79.6wt%的量存在。
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