CN101448903A - 超支化聚碳酸酯作为颜料分散剂的用途 - Google Patents
超支化聚碳酸酯作为颜料分散剂的用途 Download PDFInfo
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- CN101448903A CN101448903A CNA2007800186189A CN200780018618A CN101448903A CN 101448903 A CN101448903 A CN 101448903A CN A2007800186189 A CNA2007800186189 A CN A2007800186189A CN 200780018618 A CN200780018618 A CN 200780018618A CN 101448903 A CN101448903 A CN 101448903A
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- Prior art keywords
- pigment
- group
- aliphatic
- alcohol
- aromatic
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Abstract
本发明涉及高官能度高支化或超支化聚碳酸酯作为颜料分散剂的用途。所述聚碳酸酯可通过如下步骤得到:a)如下制备一种或多种不同的缩合产物(K):a1)使至少一种通式RO[(CO)O]nR的有机碳酸酯(A)与至少一种具有至少3个OH基团的脂族、脂族/芳族或芳族醇(B)反应,同时消除醇ROH,其中R各自相互独立地为具有1-20个碳原子的直链或支化的脂族、芳族/脂族或芳族烃基,且基团R还可以相互键合成包含基团-O[(CO)O]n-的环,其中n为1-5的整数,或a2)使光气、双光气或三光气与脂族、脂族/芳族或芳族醇(B)反应,同时释放氯化氢,其中选择在反应混合物中醇(B)与碳酸酯(A)或与光气的当量比,从而使缩合产物(K)平均包含一个碳酸酯基团或氨基甲酰氯基团和超过一个OH基团或包含一个OH基团和超过一个碳酸酯基团或氨基甲酰氯基团,以及b)使步骤a)得到的缩合产物(K)进行分子间反应。
Description
本发明涉及可通过如下步骤得到的高官能度超支化聚碳酸酯作为颜料分散剂的用途:
a)如下制备一种或多种缩合产物(K):
a1)使至少一种通式RO[(CO)O]nR的有机碳酸酯(A)与至少一种具有至少3个OH基团的脂族、脂族/芳族或芳族醇(B)反应,同时消除醇ROH,其中R各自相互独立地为具有1-20个碳原子的直链或支化的脂族、芳族-脂族或芳族烃基,且基团R还可以相互键合成包含基团-O[(CO)O]n-的环,其中n为1-5的整数,或
a2)使光气、双光气或三光气与脂族、脂族/芳族或芳族醇(B)反应,同时释放氯化氢,
其中选择在反应混合物中醇(B)与碳酸酯(A)或与光气的当量比,从而使缩合产物(K)平均包含一个碳酸酯基团或氨基甲酰氯基团和超过一个OH基团或包含一个OH基团和超过一个碳酸酯基团或氨基甲酰氯基团,以及
b)使缩合产物(K)进行分子间反应。
本发明还涉及包含(I)至少一种颜料和(II)作为分散剂的至少一种这些聚碳酸酯作为主要成分的颜料制剂,以及这些颜料制剂的生产及其在着色液体应用介质和塑料中的用途。
在液体应用介质中的颜料分散要求机械力,该机械力大小取决于颜料润湿性及其对应用介质的亲和力。为了便于分散,通常使用应不仅防止颜料颗粒再团聚和形成絮凝,而且对所得颜料分散体提供额外稳定的分散剂。分散剂的技术要求是非常需要的,它们通常尤其也包括与水性体系以及与溶剂体系的宽范围的相容性以及经济的可获取性。
目前,所提出的分散剂甚至包括具有超支化或者树枝状结构的聚合物。迄今为止,为此所述的聚合物基于聚酰胺或聚酯胺(EP-A-882 772和1 295919)、聚醚(WO-A-03/62306)、聚氨酯(WO-A-02/81071和03/91347),尤其是聚酯(EP-A-882 772和1 295 919和WO-A-00/37542、02/57004和04/37928)。
树枝状聚酰胺或聚酯非常昂贵且以多步合成不方便地生产,这直接限制了它们工业应用的可能性。经由开环聚合,随后链增长或用氧化乙烯或氧化丙烯改性而多步合成以形成聚醚体系同样非常昂贵并且在工程和安全方面是不方便的。
基于酰胺、酯、酯酰胺或聚氨酯的超支化聚合物尽管可以以一步操作生产,但通常具有高特性粘度,因此仅对有限数量的溶剂有用,这有些减少了它们可能的用途。
本发明的目的是提供具有所需性能特征,尤其是低的特性粘度以及与广泛种类的颜料和溶剂良好相容以及可以以经济方式获得的分散剂。
我们发现该目的通过使用开头作为颜料分散剂所定义的高官能度超支化聚碳酸酯实现。
根据本发明使用的高官能度超支化聚碳酸酯及其合成由WO-A-2005/23234已知。还未公开的PCT/EP2006/060240描述了它们作为流动助剂的用途。
超支化聚碳酸酯为具有羟基基团和碳酸酯或氨基甲酰氯基团的未交联大分子,它们既具有结构不均一性还具有分子不均一性。它们的结构以与树枝体类似的方式起始于中心分子,但支链的链长度不均一。然而,它们还可以具有带有官能侧基的线性结构。最后,它们可组合这两种极端情况,包含线性和支化结构部分。
对本发明而言,“超支化”指支化度(DB,还参见Acta Polymerica 48,第30页,及随后各页(1997)),即每分子中树枝状连接的平均数加上末端基团的平均数除以每分子中树枝状连接的平均数加上线性连接的平均数加上末端基团的平均数为0.1-0.99,优选0.2-0.99,更优选0.2-0.95。
对本发明而言,“树枝状”应指支化度DB为0.99-1.0。
对于根据本发明使用的聚碳酸酯,可用于缩合产物(K)的原料可包括光气、双光气或三光气,优选光气(方法变型a2),但特别优选使用通式RO[(CO)O]nR的有机碳酸酯(A)(方法变型a1))。
R基团各自独立地为具有1-20个碳原子,优选1-12个碳原子,尤其是1-6个碳原子的直链或支化的脂族、脂环族、芳族-脂族(芳脂族)或芳族烃基。两个基团R还可以相互键合成包含基团-O[(CO)O]n-的环,此时R基团各自例如为亚乙基或1,2-或1,3-亚丙基。两个R基团可相同或不同,优选它们相同。它们的含义优选为脂族烃基,更优选直链或支化烷基,最优选具有1-4个碳原子的直链烷基,或取代或未取代的苯基。
合适的R基团的实例为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正己基、正庚基、正辛基、2-乙基己基、正癸基、正十二烷基、正十四烷基、正十六烷基、正十八烷基、正二十烷基、环戊基、环己基、环辛基、环十二烷基、苯基、邻甲苯基、对甲苯基和萘基。优选甲基、乙基、正丁基和苯基。
n为1-5,优选1-3,更优选1-2的整数。
碳酸酯最优选为通式RO(CO)OR(n=1)的单碳酸酯。
有用的脂族、芳族/脂族和芳族单碳酸酯的实例为碳酸二甲酯、碳酸二乙酯、碳酸二正丙酯、碳酸二正丁酯、碳酸二异丁酯、碳酸二戊酯、碳酸二己酯、碳酸二环己酯、碳酸二庚酯、碳酸二辛酯、碳酸二癸酯、碳酸二(十二烷基酯)、碳酸亚乙酯、碳酸1,2-或1,3-亚丙酯、碳酸二苯酯、碳酸二甲苯酯、碳酸二(二甲苯酯)、碳酸二萘酯、碳酸乙基苯基酯、碳酸二苄酯。
其中n大于1的碳酸酯的实例包括二碳酸二烷基酯如二碳酸二叔丁基酯,和三碳酸二烷基酯如三碳酸二叔丁基酯。
优选脂族碳酸酯,特别是碳酸二甲酯、碳酸二乙酯、碳酸二正丙酯、碳酸二正丁酯和碳酸二异丁酯。碳酸二苯酯为优选的芳族碳酸酯。
使有机碳酸酯与包含至少3个OH基团的脂族、脂环族、脂族/芳族或芳族醇(B)或与两种或更多种不同醇的混合物反应。
醇(B)可以是支化或未支化,取代或未取代,且优选具有3-26个碳原子。优选脂环族醇,更优选脂族醇。
有用的醇(B)的实例为:甘油、三羟甲基甲烷、三羟甲基乙烷、三羟甲基丙烷、三羟甲基丁烷、1,2,4-丁三醇、三(羟甲基)胺、三(羟乙基)胺、三(羟丙基)胺、季戊四醇、双甘油、三甘油、聚甘油、双(三羟甲基丙烷)、异氰脲酸三(羟甲基)酯、异氰脲酸三(羟乙基)酯、均苯三酚(phloroglucine)、间苯三酚、羟基氢醌、三羟基甲苯、三羟基二甲基苯、六羟基苯、1,3,5-苯三甲醇、1,1,1-三(4’-羟基苯基)甲烷、1,1,1-三(4’-羟基苯基)乙烷,糖类如葡萄糖,糖衍生物如山梨糖醇、甘露糖醇、苏糖醇(threitol)、赤藓醇、阿东醇(核糖醇)、阿糖醇(lyxitol)、木糖醇、卫矛醇(半乳糖醇)、麦芽糖醇和异麦芽糖醇(isomalt)和聚酯醇。
特别有用的醇(B)为它们的烷氧基化产物。三官能或更高官能的聚醚醇尤其基于与氧化乙烯、氧化丙烯或氧化丁烯或它们的混合物的反应产物,其中优选氧化乙烯和/或氧化丙烯。氧化烯的用量基于每mol醇OH基团通常为1-30,优选1-20,更优选1-10,最优选1-5mol。
特别优选的醇(B)的实例为甘油、三羟甲基乙烷、三羟甲基丙烷、1,2,4-丁三醇、季戊四醇以及它们与氧化乙烯和/或氧化丙烯的反应产物,其中非常特别优选与氧化乙烯和/或氧化丙烯的反应产物。
至少三官能醇(B)也可以以与双官能醇(B’)的混合物使用,应选择它们的混合比,以使平均OH官能度大于2。
有用的醇(B’)的实例为乙二醇,二甘醇,三甘醇,1,2-丙二醇,1,3-丙二醇,二丙二醇,三丙二醇,新戊二醇,1,2-、1,3-和1,4-丁二醇,1,2-、1,3-和1,5-戊二醇,1,6-己二醇,1,2-或1,3-环戊二醇,1,2-、1,3-或1,4-环己二醇,1,1-、1,2-、1,3-或1,4-环己烷二甲醇,双(4-羟基环己基)甲烷,双(4-羟基环己基)乙烷,2,2-双(4-羟基环己基)丙烷,1,1’-双(4-羟基苯基)-3,3,5-三甲基环己烷,间苯二酚,氢醌,4,4’-二羟基联苯,双(4-羟基苯基)硫醚,双(4-羟基苯基)砜,双(羟甲基)苯,双(羟甲基)甲苯,双(对羟基苯基)甲烷,双(对羟基苯基)乙烷,2,2-双(对羟基苯基)丙烷,1,1-双(对羟基苯基)环己烷,二羟基二苯甲酮,基于双官能醇的烷氧基化产物的双官能聚醚多元醇,平均分子量为162-2000的聚四氢呋喃,聚己内酯或基于二醇和二羧酸的聚酯醇。
双官能醇(B’)可用于微调聚碳酸酯的性能。若使用双官能醇(B’),则醇(B’)的量基于所有醇(B)和(B’)的总量通常为0.1-39.9mol%。该量优选为0.1-35mol%,更优选0.1-25mol%,最优选0.1-10mol%。
还可以使用双官能的羰基反应性化合物(A’)微调聚碳酸酯的性能。这些是指具有两个碳酸酯基团和/或羧基的化合物。
羧基可以呈游离或衍生形式,即羧酸本身或它们与一价或二价阳离子的盐,也可使用碳酰氯、羧酸酐或羧酸酯,其中优选羧酸酯和羧酸酐,羧酸酯尤其为C1-C4烷基酯,特别是甲酯、乙酯和丁酯是特别优选的。
有用的化合物(A’)的实例为二醇的二碳酸酯或二氨基甲酰氯,二醇的实例为乙二醇1,2-丙二醇,1,3-丙二醇,1,1-二甲基乙烷-1,2-二醇,2-丁基-2-乙基-1,3-丙二醇,2-乙基-1,3-丙二醇,2-甲基-1,3-丙二醇,新戊二醇,新戊二醇羟基戊酸酯,1,2-、1,3-或1,4-丁二醇,1,6-己二醇,1,10-癸二醇,异亚丙基双(4-羟基环己烷),四甲基环丁二醇,1,2-、1,3-或1,4-环己二醇,环辛二醇,降冰片烷二醇,蒎二醇,十氢化萘二醇,2-乙基-1,3-己二醇,2,4-二乙基辛烷-1,3-二醇,氢醌,双酚A,双酚F,双酚B,双酚S,2,2-双(4-羟基环己基)丙烷,1,1-、1,2-、1,3-和1,4-环己烷二甲醇和1,2-、1,3-和1,4-环己二醇。
二碳酸酯或二氨基甲酰氯(A’)例如可通过使所述二醇例如与过量的上述碳酸酯(A)或过量的氯代碳酸酯反应而制备,从而使如此得到的二碳酸酯在两侧均被基团RO(CO)-取代。还可以首先使二醇与光气反应形成对应的氯代碳酸酯,然后使这些氯代碳酸酯与醇反应。
有用的二羧酸和二羧酸酐的实例为草酸、马来酸、富马酸、琥珀酸、戊二酸、己二酸、癸二酸、十二烷二酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、壬二酸、四氢化邻苯二甲酸、1,4-环己烷二甲酸、辛二酸、邻苯二甲酸酐、四氢化邻苯二甲酸酐、六氢化邻苯二甲酸酐、四氯邻苯二甲酸酐、内亚甲基四氢化邻苯二甲酸酐、戊二酸酐、二聚脂肪酸及其异构体和氢化产物。
当使用这类双官能化合物(A’)时,它们的量基于所有碳酸酯(A)或光气和化合物(A’)一起的总量通常为0.1-40mol%,优选0.1-35mol%,更优选0.1-25mol%,最优选0.1-10mol%。
在步骤a)中制备缩合产物(K),在使有机碳酸酯(A)与醇(B)或醇混合物((B)+(B’))反应的情况下,通过从碳酸酯分子中消除单官能醇进行(变型a1)),在光气、双光气或三光气的相应反应的情况下,通过消除氯化氢进行(变型a2))。
这里必须设定醇(B)(以及合适的话(B’))与碳酸酯(A)或光气的当量比,以使所得缩合产物(K)平均包含一个碳酸酯基团或氨基甲酰氯基团和超过一个OH基团,优选至少两个OH基团,或者包含一个OH基团和超过一个碳酸酯基团或氨基甲酰氯基团,优选至少两个碳酸酯基团或氨基甲酰氯基团。
反应温度应足以使醇组分与合适的羰基组分反应。当使用碳酸酯(A)时,温度通常为60-180℃,优选80-160℃,更优选100-160℃,最优选120-140℃。当与光气反应时,温度通常为-20℃至120℃,优选0-100℃,更优选20-80℃。
缩合可在溶剂存在下进行。有用的溶剂包括有机溶剂,例如芳族和(环)脂族烃、卤代烃、酮类、酯类、酰胺类、醚类和环状碳酸酯,如癸烷、十二烷、苯、甲苯、二甲苯、溶剂石脑油、氯苯、二甲基甲酰胺和二甲基乙酰胺。
然而,优选不加入溶剂。
各组分的加入顺序通常仅起微小作用。通常明智的是向过量组分的起始装料中加入不足组分。然而,也可以在开始反应前将两种组分一起混合,然后将该混合物加热至所需的反应温度。
在步骤a)中可生产多种不同的缩合产物(K)。这可通过使用不同的醇和/或不同的碳酸酯或光气而实现。通过选择所用醇和碳酸酯或光气的比例也可得到不同的缩合产物的混合物。
缩合产物(K)具有羟基和碳酸酯或氨基甲酰氯基团作为端基,并在步骤b)中进行分子间反应(缩聚)形成本发明的高官能度超支化聚碳酸酯。
在本文中,“高官能度”是指聚碳酸酯除了形成聚合物骨架的碳酸酯基团或氨基甲酰基团以外还具有至少3个,优选至少6个,更优选至少10个官能团作为端基或侧基。官能团包括碳酸酯基团或氨基甲酰氯基团和/或OH基团。原则上对末端或侧官能团的数目没有上限限制;然而,具有非常高的官能团数目的聚合物可能具有不希望的性能,例如高粘度或不良溶解性。因此,根据本发明使用的高官能度聚碳酸酯具有通常不大于500个末端官能团或侧官能团,优选不大于100个末端官能团或侧官能团。
步骤b)的分子间缩合通常在步骤a)的缩合反应之后直接进行。需要的话,可将反应温度略微升至约60-250℃,优选80-230℃,更优选100-200℃。
为了特别加速缩聚,可以从反应平衡中除去释放的单官能醇ROH。尤其在醇的沸点≤140℃的情况下,这可通过合适的话在减压下蒸馏或者通过用在反应条件下基本惰性的气流汽提而实现,所述气流例如为氮气、水蒸气、二氧化碳或含氧气体如空气或贫氧空气。
可进一步加入催化剂或催化剂混合物以加速反应。这些催化剂或催化剂混合物可直接包括在步骤a)的原料的起始装料中,或以后加入。
有用的催化剂尤其包括催化酯化或酯交换反应的化合物,实例为无机和有机碱如碱金属氢氧化物、碳酸盐和碳酸氢盐,优选钠、钾和铯化合物,叔胺和胍,铵化合物,鏻化合物,有机金属化合物,如有机铝,有机锡,有机锌,有机钛,有机锆和有机铋化合物,以及双金属氰化物(DMC),及其混合物。
优选催化剂为氢氧化钾,碳酸钾,碳酸氢钾,二氮杂双环辛烷(DABCO),二氮杂双环壬烯(DBN),二氮杂双环十一碳烯(DBU),咪唑类如咪唑、1-甲基咪唑或1,2-二甲基咪唑,四丁醇钛,四异丙醇钛,***,二月桂酸二丁锡,二辛酸锡和乙酰丙酮锆。
基于醇或醇混合物的用量,催化剂的用量通常为50-10000ppm,优选100-5000ppm。
还可以通过加入合适的催化剂以及通过选择合适的反应温度来控制分子间缩聚。此外可经由原料的组成和反应时间进一步控制聚碳酸酯的平均分子量。
当在升高温度下缩聚时,所得聚碳酸酯通常在室温下较长时期地稳定,例如可稳定至少6周,而没有显示出混浊、沉淀和/或粘度增加。
反应可在大气压力或在减压或超计大气压下在分批、半连续或连续操作的反应器或反应器级联中进行。
存在终止分子间缩聚反应的各种方式。
例如,温度可降至反应终止且缩聚产物存储稳定的值。这通常为温度≤60℃,优选≤50℃,更优选≤40℃,最优选室温的情况。
还可以钝化催化剂。在碱性催化剂情况下,这可通过加入酸性组分如路易斯酸或者有机或无机质子酸如磷酸而简单进行。
还可以用预冷却的溶剂稀释而终止反应。当必须通过加入溶剂而调节反应混合物的粘度时,这是特别优选的。
最后,还加入具有对缩合产物(K)的焦点基团呈反应性的官能团的组分而终止缩聚。例如,在碳酸酯基团或氨基甲酰基焦点基团的情况下,可以加入单胺、二胺或多胺。在羟基焦点基团的情况下,例如加入与OH基团反应的单-、二-或多异氰酸酯、含有环氧基团的化合物或酸衍生物。
如果选择合适的反应条件,如此合成的聚碳酸酯通常可无需进一步提纯而用于所需应用。
然而,需要的话,可例如借助用活性炭或金属氧化物以0.1-50重量%,优选0.5-25重量%,更优选1-10重量%的量例如在10-100℃,优选20-80℃,更优选30-60℃的温度下处理而对所得反应混合物进行脱色,其中所述金属氧化物例如为铝土、硅石、氧化镁、氧化锆、氧化硼或其混合物。
合适的话,还可以过滤反应混合物以除去任何存在的沉淀物。
需要的话,还可通过将缩聚产物汽提而除去低分子量的挥发性化合物。为此,在达到所需聚合度后,可任选钝化催化剂并可以通过蒸馏除去低分子量挥发组分如一元醇、酚、碳酸酯、氯化氢或挥发性低聚或环状化合物,合适的话在蒸馏中引入气体,优选氮气、二氧化碳或空气,以及合适的话在减压下进行蒸馏。
根据本发明使用的聚碳酸酯是支化,但未交联的。
在本文中,“未交联”是指通过聚合物的不溶性级份测定的交联度≤15重量%,更优选≤10重量%。
聚合物的不溶性级份通过在索氏萃取器中并使用与凝胶渗透色谱法相同的溶剂(四氢呋喃、二甲基乙酰胺或六氟异丙醇)萃取4小时,并将残留物干燥至恒重之后称重而测定。
根据本发明使用的聚碳酸酯理想地平均具有一个碳酸酯或氨基甲酰氯基团作为焦点基团和超过两个OH基团或者具有一个OH基团作为焦点基团和超过两个碳酸酯或氨基甲酰氯基团。反应性基团的数目取决于缩合产物(K)的组成和缩聚度。
当除了羟基、碳酸酯和氨基甲酰氯基团之外还含有其它官能团或官能单元的组分包括在缩聚反应中时,根据本发明使用的聚碳酸酯除了已经存在的羟基、碳酸酯和氨基甲酰氯基团之外,还可包含其它官能团。
额外的官能团或官能单元例如可为氨基甲酸酯基团、伯氨基、仲氨基、叔氨基、醚基团、羧酸基或其衍生物、磺酸基或其衍生物、膦酸基或其衍生物、硅烷基团、硅氧烷基团、芳基或长链烷基。
其掺入带来用这些基团官能化的组分的实例如下所列:
-氨基甲酸酯基团:例如乙醇胺,丙醇胺,异丙醇胺,2-(丁基氨基)乙醇,2-(环己基氨基)乙醇,2-氨基-1-丁醇,2-(2’-氨基乙氧基)乙醇或氨的高级烷氧基化产物,4-羟基哌啶,1-羟乙基哌嗪,二乙醇胺,二丙醇胺,二异丙醇胺,三(羟甲基)氨基甲烷,三(羟乙基)氨基甲烷,乙二胺,丙邻二胺,六亚甲基二胺或异佛尔酮二胺,烷基和芳基异氰酸酯,烷基和芳基二异氰酸酯;
-巯基:例如巯基乙醇;
-叔氨基:例如三乙醇胺、三丙醇胺、N-甲基二乙醇胺、N-甲基二丙醇胺或N,N-二甲基乙醇胺;
-醚基团:例如具有两个或更多个官能团的聚醚醇;
-酯基:例如二羧酸、三羧酸,二羧酸酯如对苯二甲酸二甲酯或三羧酸酯;
-长链烷基:例如长链链烷醇或链烷二醇,烷基异氰酸酯和烷基二异氰酸酯;
-尿烷和脲基团:例如伯胺和仲胺。
存在于聚碳酸酯中的羟基、碳酸酯和氨基甲酰基也可由随后已经存在的基团转官能化(transfunctionalized)。
例如,羟基可转化为如下基团:酯或尿烷基团,其可通过加入包含酸基或异氰酸酯的分子而得到。酸基可通过与酸酐基团反应而形成。最后,聚碳酸酯可用氧化烯,尤其是氧化乙烯、氧化丙烯或氧化丁烯而转化成高官能度聚碳酸酯聚醚多元醇。
根据本发明使用的聚碳酸酯的平均分子量Mw通常为500-500000,优选1000-150000,更优选1000-50000,最优选1500-25000。
根据本发明使用的聚碳酸酯的多分散性Mw/Mn通常为1.1-50,优选1.2-40,更优选1.2-35。
根据本发明使用的聚碳酸酯是颜料的优异分散剂。它们有助于将颜料分散于它们的应用介质中并导致它们总的性能的提高,尤其是它们的颜色性能,其中实例为颜色强度和透明度,以及它们的流变性能,其中实例为在液体应用介质中的低粘度和抗絮凝性。
根据本发明使用的聚碳酸酯可与颜料分开,优选预先或同时掺入各应用介质中。然而,优选预先用颜料处理它们以形成液体或优选的固体颜料制剂。
因此,本发明还提供了颜料制剂,其包含:
(I)至少一种颜料
和
(II)作为分散剂的至少一种本发明聚碳酸酯。
优选本发明颜料制剂基于制剂重量包含1-50重量%聚碳酸酯(II)。
颜料制剂可进一步包含常规助剂,如表面活性添加剂,尤其是基于颜料衍生物的那些(所谓的颜料协同增效剂)作为额外组分。
用于本发明液体颜料制剂的其它助剂尤其还包括粘合剂、交联剂、助留剂、增稠剂、生物杀伤剂和/或额外的分散剂。
当将额外的助剂用于本发明颜料制剂时,它们的含量通常为至多10重量%。
本发明液体颜料制剂优选为水性的,即它们包含水或水和有机溶剂如醇,尤其是具有保水效果的溶剂的混合物作为液相。液相通常包含50-90重量%的这些颜料制剂。
优选本发明颜料制剂为固体制剂。
本发明聚碳酸酯(II)分散剂在固体颜料制剂中的水平可更高或更低。
具有较低水平的聚碳酸酯的合适的颜料制剂(也已知为“表面改性的颜料”)的合适组成通常为80-99重量%,尤其是90-98重量%颜料(I)和1-20重量%,尤其是2-10重量%聚碳酸酯(III)。
用聚碳酸酯(II)表面改性的颜料表现出所有上述正性能特征如容易分散(dispersion softness)、高颜色强度、高透明度和抗絮凝性,并且对着色任何类型的有机和无机材料非常有用。
液体应用介质可为纯水性的;包含水和有机溶剂如醇的混合物;或者仅基于有机溶剂如醇,二醇醚,酮如甲基乙基酮,酰胺如N-甲基吡咯烷酮和二甲基甲酰胺,酯如乙酸乙酯、乙酸丁酯和乙酸甲氧基丙酯,芳族或脂族烃如二甲苯,矿物油和溶剂油(mineral spirit)。优选水性应用介质。
可用本发明颜料制剂着色的材料的实例包括:
-涂料,如建筑涂料、工业涂料、汽车涂料、可辐照固化的涂料;
-漆,用于建筑物外部和建筑物内部的漆,其中实例为木漆、刷白、刷墙粉、乳胶漆;
-印刷油墨,如胶版印刷油墨、柔性版印刷油墨、甲苯凹版印刷油墨、印染油墨、可辐照固化印刷油墨;
-墨水,包括喷墨墨水;
-滤色剂;
-建筑材料,例如硅酸盐打底体系,水泥,混凝土,砂浆,石膏;
-沥青;
-纤维素材料,例如纸张、纸板、卡片纸板、木材和木基材料,其可被涂覆或者整理;
-粘合剂和密封剂;
-成膜聚合物保护胶体,其例如用于药物工业;
-化妆品制品;
-清洁剂;
-塑料,
不仅是改性的天然材料,如热固性塑料,如酪蛋白塑料;热塑性塑料,如硝酸纤维素、醋酸纤维素、纤维素混合酯和纤维素醚,
还有合成塑料,如:
缩聚物:热固性塑料,如酚醛树脂、脲醛树脂、硫脲树脂、蜜胺树脂、不饱和聚酯树脂、丙烯酸类树脂、聚硅氧烷、聚酰亚胺和聚苯并咪唑;热塑性塑料,例如聚酰胺、聚碳酸酯、聚酯、聚苯醚、聚砜和聚乙烯缩醛;
加成聚合物:热塑性塑料如聚烯烃,如聚乙烯、聚丙烯、聚-1-丁烯和聚-4-甲基-1-戊烯、离聚物、聚氯乙稀、聚偏二氯乙烯、聚甲基丙烯酸甲酯、聚丙烯腈、聚苯乙烯、聚缩醛、氟化聚合物、聚乙烯醇、聚乙酸乙烯酯和对二甲苯,以及共聚物如乙烯-乙酸乙烯酯共聚物、苯乙烯-丙烯腈共聚物、丙烯腈-丁二烯-苯乙烯共聚物、聚对苯二甲酸乙二醇酯和聚对苯二甲酸丁二醇酯;
加聚物:热固性塑料,如环氧树脂和交联的聚氨酯;热塑性塑料如线性聚氨酯和氯化聚醚。
具有较高水平分散聚碳酸酯(II)的本发明固体颜料制剂通常包含50-95重量%,优选70-85重量%颜料(I)和5-50重量%,优选15-30重量%聚碳酸酯(II)。
在该组成范围内的本发明颜料制剂除了上文对表面改性颜料所述的有利性能特征之外,特征还在于与含水和非水性液体应用介质特别显著的相容性,尤其是拌合特征,即它们可以非常低的能量输入分散在它们的应用介质中。
对于液体应用介质,这可通过简单搅拌或振摇而实现,而对于塑料,这例如可通过一起挤出(优选使用单螺杆或双螺杆挤出机)、滚动、捏合或研磨而实现,此时,塑料可以以塑化变形的物料或熔体存在并加工成由塑料、膜和纤维制成的成型制品。
本发明聚碳酸酯可用于分散有机和无机颜料。因此,本发明颜料制剂可包含有机或无机颜料作为组分(I)。
应理解的是,如同分散组分(II),颜料组分也可包含颜料混合物,即各种有机或各种无机颜料的混合物,或(多种)有机和(多种)无机颜料的混合物。
颜料以细碎形式存在于颜料制剂中,因此,它们的平均粒度通常为0.02-5μm。
有机颜料通常包括有机彩色颜料和黑色颜料。无机颜料同样可为有色颜料(彩色、黑色和白色颜料)以及发光颜料以及通常用作填料的无机颜料。有用的有机彩色颜料的实例包括:
-单偶氮颜料:C.I.颜料棕25;C.I.颜料橙5、13、36、38、64和67;C.I.颜料红1、2、3、4、5、8、9、12、17、22、23、31、48:1、48:2、48:3、48:4、49、49:1、51:1、52:1、52:2、53、53:1、53:3、57:1、58:2、58:4、63、112、146、148、170、175、184、185、187、191:1、208、210、245、247和251;C.I.颜料黄1、3、62、65、73、74、97、120、151、154、168、181、183和191;C.I.颜料紫32;
-双偶氮颜料:C.I.颜料橙16、34、44和72;C.I.颜料黄12、13、14、16、17、81、83、106、113、126、127、155、174、176、180和188;
-双偶氮缩合颜料:C.I.颜料黄93、95和128;C.I.颜料红144、166、214、220、221、242和262;C.I.颜料棕23和41;
-三苯并[cd,jk]芘-5,10-二酮颜料:C.I.颜料红168;
-蒽醌颜料:C.I.颜料黄147、177和199;C.I.颜料紫31;
-蒽素嘧啶颜料:C.I.颜料黄108;
-喹吖啶酮颜料:C.I.颜料橙48和49;C.I.颜料红122、202、206和209;C.I.颜料紫19;
-喹酞酮颜料(Quinophthalone):C.I.颜料黄138;
-二酮基吡咯并吡咯颜料:C.I.颜料橙71、73和81;C.I.颜料红254、255、264、270和272;
-二噁嗪颜料:C.I.颜料紫23和37;C.I.颜料蓝80;
-黄烷士酮颜料:C.I.颜料黄24;
-阴丹酮颜料:C.I.颜料蓝60和64;
-二氢异吲哚颜料:C.I.颜料橙61和69;C.I.颜料红260;C.I.颜料黄139和185;
-异吲哚啉酮颜料:C.I.颜料黄109、110和173;
-异宜和蓝酮颜料:C.I.颜料紫31;
-金属配合物颜料:C.I.颜料红257;C.I.颜料黄117、129、150、153和177;C.I.颜料绿8;
-紫环酮颜料:C.I.颜料橙43;C.I.颜料红194;
-苝系颜料:C.I.颜料黑31和32;C.I.颜料红123、149、178、179、190和224;C.I.颜料紫29;
-酞菁颜料:C.I.颜料蓝15、15:1、15:2、15:3、15:4、15:6和16;C.I.颜料绿7和36;
-皮蒽酮颜料:C.I.颜料橙51;C.I.颜料红216;
-吡唑并喹唑酮(Pyrazoloquinazolone)颜料:C.I.颜料橙67;C.I.颜料红251;
-硫靛颜料:C.I.颜料红88和181;C.I.颜料紫38;
-三芳基碳鎓颜料:C.I.颜料蓝1、61和62;C.I.颜料绿1;C.I.颜料红81、81:1和169;C.I.颜料紫1、2、3和27;
-C.I.颜料黑1(苯胺黑);
-C.I.颜料黄101(醛连氮黄);
-C.I.颜料棕22。
有用的无机着色颜料的实例包括:
-白色颜料:二氧化钛(C.I.颜料白6)、锌白、着色氧化锌;硫化锌、锌钡白;
-黑色颜料:氧化铁黑(C.I.颜料黑11)、铁锰黑、尖晶石黑(C.I.颜料黑27);碳黑(C.I.颜料黑7);
-彩色颜料:氧化铬、水合氧化铬绿;铬绿(C.I.颜料绿48);钴绿(C.I.颜料绿50);群青绿;钴蓝(C.I.颜料蓝28和36;C.I.颜料蓝72);群青蓝;锰蓝;群青紫;钴紫和锰紫;氧化铁红(C.I.颜料红101);硫硒化镉(C.I.颜料红108);硫化硒(C.I.颜料红265);钼铬红(C.I.颜料红104);群青红;
氧化铁棕(C.I.颜料棕6和7)、混合棕、尖晶石相和刚玉相(C.I.颜料棕29、31、33、34、35、37、39和40)、铬钛黄(C.I.颜料棕24)、铬橙;硫化镉(C.I.颜料橙75);氧化铁黄(C.I.颜料黄42);镍钛黄(C.I.颜料黄53;C.I.颜料黄157、158、159、160、161、162、163、164和189);铬钛黄;尖晶石相(C.I.颜料黄119);硫化镉和硫化镉锌(C.I.颜料黄37和35);铬黄(C.I.颜料黄34);钒酸铋(C.I.颜料黄184);
通常用作填料的无机颜料的实例为透明硅石、石英粉末、矾土、氢氧化铝、天然云母、天然和沉淀白垩和硫酸钡。
发光颜料尤其为具有单相或多相结构的片状颜料,其颜色由干涉、反射和吸收现象的相互影响而显著。实例为铝片和铝、铁氧化物以及具有一个或多个尤其是金属氧化物涂层的云母片。
优选颜料(I)的实例为酞菁颜料、阴丹酮颜料和苝系颜料。
本发明固体颜料制剂可有利地通过同样根据本发明的生产方法,通过使所述颜料(I)和所述分散剂(II)一起在液体介质存在下或在干燥状态下粉碎,以及合适的话随后除去液体介质而得到。
粉碎操作优选包括在液体介质中或在干燥状态下研磨。
干磨例如可在球磨机、摆动磨机、行星式磨机或磨碎机中进行。合适的研磨介质的实例为钢球、硅/铝/锆氧化物(SAZ)珠粒、玻璃珠和玛瑙球,其直径通常为0.1-10cm,优选2-5cm。
本方法的优选方案包括湿磨,尤其是在包含至少一部分分散剂(II)的含水悬浮液中湿磨。
搅拌球磨机是为此特别有用的研磨组件。优选研磨介质为SAZ珠粒,其直径尤其为0.4-3mm。
所用液体介质优选为水,但也可使用水特别是与水溶性或水溶混性有机溶剂如醇的混合物。
颜料可以以干燥粉末或压缩饼的形式用于本发明方法。
所用颜料(I)优选包含整理产品,即颜料的初级粒度已经设定至计划应用的所需值。然而,也可使用未整理的颜料。在无机颜料如氧化物和钒酸铋颜料的情况下,初级粒度通常在合成颜料的过程中设定,以使产生的颜料悬浮液可直接用于本发明方法。
取决于干燥方法的选择-喷雾造粒和流化床干燥、喷雾干燥、在桨式干燥器中干燥、蒸发和随后粉碎-本发明颜料制剂的次级粒度也可以特定方式控制。
喷雾和流化床造粒可产生平均粒度例如为50-5000μm,尤其是100-1000μm的粗碎细粒。喷雾干燥通常产生平均粒度例如为50-500μm的细粒。细碎制剂可通过在桨式干燥器中干燥和通过蒸发,随后解聚集研磨而得到。然而,优选本发明颜料制剂呈细粒形式。
喷雾造粒优选在喷雾塔中使用单材质喷嘴进行。此处,悬浮液以较大液滴形式喷雾分散并且水蒸发。分散剂(II)在干燥温度下已经是液体或熔体,从而导致具有特别光滑表面的基本球形细粒的形成(BET值通常≤15m2/g,尤其是≤10m2/g)。
在喷雾塔中气体入口温度通常为150-300℃,优选160-200℃。气体出口温度通常为70-150℃,优选70-130℃。
所得细粒颜料的残留水分含量优选<2重量%。
实施例
A.生产本发明颜料制剂
A.1.生产用作分散剂的聚碳酸酯
将多官能醇A、碳酸二乙酯和催化剂K(基于醇的量为250ppm)以表1所报道的摩尔比置于配有搅拌器、回流冷凝器和内部温度计的三颈烧瓶中作为初始装料。然后将混合物加热至120℃,在标有*的情况下加热至140℃,并在该温度下搅拌2小时。随着反应进行,由于确保所释放乙醇的蒸发冷却,反应混合物的温度下降。在用下降式冷凝器代替回流冷凝器且每当量催化剂K加入一当量磷酸之后,蒸除释放的乙醇,并且反应混合物的温度逐渐降低到160℃。通过称重蒸除的醇测定转化率并且在表1中以基于理论上可能的完全转化的mol%报道。
所得聚碳酸酯的平均分子量MW(Mw和Mn)随后通过凝胶渗透色谱法使用二甲基乙酰胺作为移动相和聚甲基丙烯酸甲酯(PMMA)作为标准而测定。
所得聚碳酸酯的粘度[mPas]在23℃下根据德国标准规范DIN53019第1部分测量。它们的OH数[mg KOH/g]根据DIN53240第2部分测量。
关于这些实验和它们的结果的其它细节汇集在表1中。所用缩写具有如下含义:
TMP:三羟甲基丙烷
DEC:碳酸二乙酯
PO:氧化丙烯
EO:氧化乙烯
表1
聚碳酸酯 | 醇A | 摩尔比A:DEC | 催化剂K | 转化率[mol%] | MW[g/mol]MwMn | 粘度[mPas] | OH数[mg KOH/g] |
P1 | TMP×1.2 PO/mol TMP | 1:1 | K2CO3 | 70 | 21001450 | 7220 | 461 |
P2* | TMP×5.4 PO/mol TMP | 1:1 | KOH | 70 | 78002500 | 1260 | 227 |
P3 | TMP×12 EO/mol TMP | 1:1 | K2CO3 | 90 | 55002700 | 990 | 164 |
A.2.生产颜料制剂
以2步生产颜料制剂。首先,将xg颜料(I)和yg超支化聚碳酸酯(II)的悬浮液悬浮在200g水(实施例1和2)或88g水(实施例3)中,用二甲基乙醇胺(实施例1和2)或氨(实施例3)将pH调至8并使用直径为1.0-1.6mm(实施例1和2)或0.5-0.75mm(实施例3)的SAZ珠粒在搅拌球磨机中研磨至d50值<1μm。在除去SAZ珠粒之后,然后将所得分散体在喷雾塔中用单材质喷嘴(气体入口温度160-170℃,气体出口温度70-80℃)通过造粒而喷雾干燥。
所生产的颜料制剂的组成描述于表2。
表2
B.测试所得颜料制剂
B.1.在含水涂料体系中使用
第一步为生产各自包含15重量%的分别为实施例1和2的颜料制剂的含水着色糊。为此,将100g WO-A-92/15405的实施例1.3中所述的聚氨酯树脂水分散体、32.4g实施例1的颜料制剂或28.4g实施例2的颜料制剂和相应量的水的混合物用二甲基乙醇胺将pH调至8并在含有直径为1.0-1.6mm的SAZ珠粒的搅拌球磨机中研磨4小时。
然后,通过在每种情况下向225g基于聚氨酯的共混清漆(描述于WO-A-92/15405的实施例3)中加入34g所得含水着色糊而生产涂料。随后,加入7.5g水,使用氨基乙醇建立pH为8。然后使用螺旋桨式搅拌器将所得悬浮液在1000rpm下搅拌15分钟。
对于对比V,以类似的方式生产基于整理但未表面改性的实施例1和2所用的颜料(使用27g C.I.颜料红179)的含水着色糊和含水涂料。
通过使用流动薄板(flow sheet)测量含水着色糊的流动时间(等级5)而测定粘度。
流动薄板具有锯齿。该锯齿的中间点对应于等级1。沿着流动薄板的边缘以40mm的间隔标记,这对应于等级2-5。
然后,将3g所得着色糊试样称重入在水平位置平躺的流动薄板的锯齿中。在水平储存5分钟之后,将流动薄板垂直悬挂,以使着色糊能够向下流动。
通过测量流动时间,以得到等级2至等级5而评价流动能力。流动时间越短,着色糊的粘度越低。
通过白色还原测定颜色强度。为此,将1.6g各个所得涂料与1.0g用二氧化钛(Kronos2310)着色40重量%的白色糊混合(白色还原约1/3标准色度)、以150μm厚的层施加至盘、闪蒸并在130℃下烘烤30分钟。
将对比颜料V的着色指定为100的FAE颜色当量值(标准)。FAE颜色当量值<100表示比标准高的颜色强度,而FAE颜色当量值>100表示更低的颜色强度。
透明度通过将上述涂料以200μm的层厚引至一块黑色和白色纸板并在干燥之后测定,通过与使用V颜料制备的对比试样比较而测定相对于黑色的散射ΔE(ddE)。负值表示更高的透明度。
所得结果汇集在表3中。
表3
颜料制剂 | 流动时间[s] | FAE | 透明度(ddE) |
1 | 25 | 94 | -2.2 |
2 | 41 | 91 | -1.5 |
V | 88 | 100 | - |
B.2.在基于溶剂的烤漆中使用
通过白色还原用实施例3的制剂整理的醇酸-蜜胺烤漆而测定实施例3的颜料制剂的颜色强度。
将0.2g颜料制剂(对应于0.16g颜料)、10g Kronos 2310二氧化钛和10g醇酸-蜜胺烤漆(固含量约55重量%)的混合物在具有15g 2mm直径玻璃珠的Skandex振摇器中振摇30分钟,然后使用100μm的线绕刮漆器施加到纸板,在闪蒸10分钟之后,在120℃下烘烤30分钟。
与用实施例3使用的0.16g整理的C.I.颜料蓝15:3着色的且不包含聚碳酸酯的涂料相比较表明本发明颜料制剂显著更高的颜色强度。
Claims (10)
1.可通过如下步骤得到的高官能度超支化聚碳酸酯作为颜料分散剂的用途:
a)如下制备一种或多种不同的缩合产物(K):
a1)使至少一种通式RO[(CO)O]nR的有机碳酸酯(A)与至少一种具有至少3个OH基团的脂族、脂族/芳族或芳族醇(B)反应,同时消除醇ROH,其中R各自相互独立地为具有1-20个碳原子的直链或支化的脂族、芳族-脂族或芳族烃基,且基团R还可以相互键合成包含基团-O[(CO)O]n-的环,其中n为1-5的整数,或
a2)使光气、双光气或三光气与脂族、脂族/芳族或芳族醇(B)反应,同时释放氯化氢,
其中选择在反应混合物中醇(B)与碳酸酯(A)或与光气的当量比,从而使缩合产物(K)平均包含一个碳酸酯基团或氨基甲酰氯基团和超过一个OH基团或包含一个OH基团和超过一个碳酸酯基团或氨基甲酰氯基团,
以及
b)使来自步骤a)的缩合产物(K)进行分子间反应。
2.一种颜料制剂,包含:
(I)至少一种颜料
和
(II)作为分散剂的至少一种根据权利要求1的高官能度超支化聚碳酸酯。
3.根据权利要求2的颜料制剂,基于所述制剂重量包含1-50重量%组分(II)。
4.根据权利要求2的颜料制剂,包含80-99重量%组分(I)和1-20重量%组分(II)。
5.根据权利要求2的颜料制剂,包含50-95重量%组分(I)和5-50重量%组分(II)。
6.一种生产根据权利要求4或5的颜料制剂的方法,其包括使所述颜料(I)和所述分散剂(II)一起在液体介质存在下或在干燥状态下粉碎,以及合适的话随后除去液体介质。
7.根据权利要求6的方法,其中使所述颜料(I)首先在包含至少一部分所述分散剂(II)的含水悬浮液中经受湿粉碎,然后将所述悬浮液干燥,合适的话在加入剩余分散剂(II)之后干燥。
8.根据权利要求2-5中任一项的颜料制剂在着色液体应用介质中的用途。
9.根据权利要求8的用途,其中所述液体应用介质为涂料、墨水、印刷油墨或整理体系,其中液相包含水、有机溶剂或水和有机溶剂的混合物。
10.根据权利要求2-5中任一项的颜料制剂在着色塑料中的用途。
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US (1) | US20090093589A1 (zh) |
EP (1) | EP2027214B1 (zh) |
JP (1) | JP2009537682A (zh) |
KR (1) | KR20090019858A (zh) |
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2007
- 2007-05-15 EP EP07729169A patent/EP2027214B1/de not_active Not-in-force
- 2007-05-15 US US12/299,323 patent/US20090093589A1/en not_active Abandoned
- 2007-05-15 KR KR1020087031254A patent/KR20090019858A/ko not_active Application Discontinuation
- 2007-05-15 JP JP2009511468A patent/JP2009537682A/ja active Pending
- 2007-05-15 CN CNA2007800186189A patent/CN101448903A/zh active Pending
- 2007-05-15 WO PCT/EP2007/054721 patent/WO2007135032A2/de active Application Filing
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Cited By (3)
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CN107915851A (zh) * | 2017-12-22 | 2018-04-17 | 叶青华 | 提高注塑人体模型色彩均匀与稳定性的色料及方法 |
CN113278126A (zh) * | 2021-03-04 | 2021-08-20 | 奥斯佳材料科技(上海)有限公司 | 一种生物基聚氨酯色浆及其制备方法 |
CN116694165A (zh) * | 2023-07-10 | 2023-09-05 | 诸城市万众福利涂料有限公司 | 一种耐腐蚀水性涂料及其制备方法 |
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WO2007135032A2 (de) | 2007-11-29 |
ATE546496T1 (de) | 2012-03-15 |
US20090093589A1 (en) | 2009-04-09 |
JP2009537682A (ja) | 2009-10-29 |
WO2007135032A3 (de) | 2008-01-17 |
KR20090019858A (ko) | 2009-02-25 |
EP2027214A2 (de) | 2009-02-25 |
EP2027214B1 (de) | 2012-02-22 |
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