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CN106574132A - 在分散体中作为表面活性成分的贫voc的胺 - Google Patents

在分散体中作为表面活性成分的贫voc的胺 Download PDF

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CN106574132A
CN106574132A CN201580042343.7A CN201580042343A CN106574132A CN 106574132 A CN106574132 A CN 106574132A CN 201580042343 A CN201580042343 A CN 201580042343A CN 106574132 A CN106574132 A CN 106574132A
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R·库普费尔
C·泽芬
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Clariant International Ltd
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Abstract

本发明的主题是分散体，所述分散体包含(A)至少一种式(I)的化合物，其中R1表示H、C1‑C4‑烷基、CH2CH2OH或CH2CH(CH3)OH，(B)聚合物粘结剂，和(C)水。

Description

在分散体中作为表面活性成分的贫VOC的胺
本发明的主题是作为含水分散体的中和剂和稳定剂的源自再生性原料的贫VOC的无味的胺。
根据现有技术，在含水分散体油漆中典型地使用含氨溶液或胺(例如2-氨基-2-甲基-1-丙醇)充当碱。然而所述化合物的特征在于其胺类型的气味及其VOC含量。由于这样的挥发性有机化合物连同紫外线辐射和NOx促进臭氧形成，许多国家已经通过了用于减少VOC含量的法规(例如2004/42/EG)。此外关于环保，所述法规用于保护居民免受由于空气有害物质造成的健康损害。
WO 2013/123153描述了一种非离子型表面活性剂，所述非离子型表面活性剂具有一个或多个胺官能以及作为亲水部分的一个或多个烷基链。
WO 2010/126657或US 2010/0326320中描述了三羟基单胺或三羟基二胺在含水油漆中的中和能力。还描述了所得油漆和涂料的粘度、遮盖力、黄化、光泽度、耐湿磨损性和粘着力方面的性能。
WO 2014/003969中描述了羧基二胺，羧基二胺能够在油漆、涂料和清洁剂中充当贫VOC的中和剂。然而羧基二胺只能通过多步合成由石油化学原料获得。
EP 0614881、US 5449770和US 2016962描述了用于制备源自葡萄糖的葡糖胺的方法。
EP 1676831一般性地描述了二烷基葡糖叔胺(例如二乙基葡糖胺)的制备及其在含水刷抹料中作为表面活性剂的用途，但是没有提到具体实施例。
发明的目的在于找到一种胺，所述胺由再生性原料制得并且可以借助其调节pH值，从而可以制备水分散体油漆。此外所述胺应当无VOC。
出人意料地发现，通过基于再生性原料葡萄糖的胺能够实现所述目的。
因此本发明的主题为分散体，所述分散体包含
(A)至少一种式(I)的化合物
其中R1表示H、C1-C4-烷基、CH2CH2OH或CH2CH(CH3)OH，
(B)聚合物粘结剂
和
(C)水。
所述分散体还可以包含含水分散体油漆的常规成分。常规成分可以是：颜料和助剂，其中术语“颜料”表示颜料以及更宽意义上的填料。助剂可以特别是润湿剂和分散剂、消泡剂、杀生物剂、聚结剂以及流变添加剂。
化合物(I)为多羟基胺，其中R1可以是H、C1-C4-烷基、CH2CH2OH或CH2CH(CH3)OH。优选地，R1为H、甲基或CH2CH2OH。多羟基单元为己糖，优选差向异构体葡萄糖。用于制备式(I)的烷基葡糖胺的方法是本领域技术人员公知的。对于R＝C1至C4-烷基的化合物，例如根据EP-A-1676831中给出的方法通过在氢气和过渡金属催化剂的存在下使用醛或酮对N-烷基多羟基胺进行还原烷基化进行制备。羟乙基-N-甲基-葡糖胺和羟丙基-N-甲基-葡糖胺可以通过N-甲基葡糖胺与氧化乙烯或氧化丙烯在水溶液中的反应制得。式(I)的化合物可以以纯物质或水溶液的形式使用。由于叔胺(如二甲基葡糖胺、羟乙基-N-甲基-葡糖胺和羟丙基-N-甲基-葡糖胺)不太容易形成亚硝胺，它们对于根据本发明的分散体来说是优选的。
聚合物粘结剂组分(B)为烯属不饱和单体的均聚物或共聚物。优选的烯属不饱和单体为例如
-乙烯基单体，如乙烯醇的羧酸酯，例如乙酸乙烯酯、丙酸乙烯酯、异壬酸或异癸酸(也被称为C9和C10支链烷烃羧酸)的乙烯基醚，
-芳基取代的烯烃，如苯乙烯和二苯乙烯，
-烯属不饱和羧酸酯，如丙烯酸甲酯、丙烯酸乙酯、丙烯酸丙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸戊酯、丙烯酸己酯、丙烯酸2-乙基己酯、丙烯酸十三酯、丙烯酸十八酯、丙烯酸羟乙酯、丙烯酸羟丙酯和相应的甲基丙烯酸酯，
-烯属不饱和二羧酸酯，如马来酸二甲酯、马来酸二乙酯、马来酸二丙酯、马来酸二丁酯、马来酸二戊酯、马来酸二己酯和二-2-乙基己基马来酸酯，
-烯属不饱和羧酸和二羧酸，如丙烯酸、甲基丙烯酸、衣康酸、马来酸和富马酸，及其钠盐、钾盐和铵盐，
-烯属不饱和磺酸和膦酸及其碱金属盐和铵盐，如乙烯基磺酸、乙烯基膦酸、丙烯酰氨基甲基丙烷磺酸及其碱金属盐和铵盐、烷基铵盐和羟烷基铵盐、烯丙基磺酸及其碱金属盐和铵盐、丙烯酰氧乙基膦酸及其铵盐和碱金属盐，以及相应的甲基丙烯酸衍生物，
-烯属不饱和胺、铵盐、腈和酰胺，如二甲氨基乙基丙烯酸酯、丙烯酰氧乙基三甲基卤化铵、丙烯腈、丙烯酰胺、甲基丙烯酰胺、N-甲基丙烯酰胺、N-乙基丙烯酰胺、N-丙基丙烯酰胺、N-羟甲基丙烯酰胺，以及相应的甲基丙烯酸衍生物和乙烯基甲基乙酰胺。
为了制备根据本发明的含水分散体所使用的组分(C)水优选以蒸馏水或去离子水的形式使用。也可以使用饮用水(自来水)和/或天然来源的水。
合适的颜料为细粒的有机或无机的白色颜料或彩色颜料，或不同的这些颜料的混合物。
特别优选的有机颜料的示例性选择为炭黑颜料，例如气黑或炉黑；单偶氮颜料和双偶氮颜料，尤其是染料索引(Color Index)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-萘酚颜料和萘酚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254、颜料红256、颜料橙5、颜料橙38或颜料棕1；涂漆的偶氮颜料和金属络合物颜料，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；异吲哚啉酮颜料和异吲哚啉颜料，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；蒽嵌蒽醌颜料、蒽醌颜料、喹吖啶酮颜料、二噁嗪颜料、靛蒽醌颜料、二萘嵌苯颜料、紫环酮颜料；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；三芳基正碳颜料，尤其是染料索引颜料颜料红169、颜料蓝56或颜料蓝61。
合适的无机颜料例如为二氧化钛、硫化锌、氧化锌、氧化铁、磁铁矿、锰铁氧化物、氧化铬、群青、镍锑钛氧化物或铬锑钛氧化物、锰钛金红石、氧化钴、钴和铝的混合氧化物、金红石混相颜料、稀土元素的硫化物、钴与镍和锌的尖晶石、基于铁和铬与铜锌以及锰的尖晶石、钒酸铋以及体质颜料；尤其使用颜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；也被称为填料的碳酸钙如天然产生的白垩和沉淀碳酸钙、白云石、天然二氧化硅(石英粉)、热解二氧化硅和沉淀二氧化硅、硅藻土、氧化铝、氢氧化铝、滑石、高岭土、云母(硅酸铝钾水合物)、硫酸钡如天然产生的重晶石和沉淀硫酸钡粉。优选还经常使用无机颜料的混合物。也经常使用有机颜料与无机颜料的混合物。
合适的润湿剂和分散剂优选为聚丙烯酸盐、丙烯酸酯共聚物和MAS共聚物、烷基酚乙氧基化物和烷基酚乙氧基化物替代品，如Guerbet衍生物，脂肪酸衍生物和脂肪醇衍生物，尤其是其烷氧基化物，以及EO/PO均聚物和嵌段共聚物和聚硅氧烷醚。
合适的消泡剂优选为矿物油消泡剂及其乳液、硅油消泡剂和硅油乳液、聚亚烷基二醇、聚亚烷基二醇脂肪酸酯、脂肪酸、高级醇、磷酸酯、疏水改性的二氧化硅、三硬酯酸铝、聚乙烯蜡和酰胺蜡。
用于阻止细菌、藻类和真菌的失控传播的合适的杀生物剂为甲醛、甲醛供体化合物、甲基异噻唑啉酮、氯甲基异噻唑啉酮、苯并异噻唑啉酮、溴硝丙二醇、二溴二氰基丁烷，和氯化银涂布的二氧化钛。
合适的聚结剂为酯和酮，如苯甲酸酯和丁酸酯，以及醚醇和二醇。作为聚结剂尤其提及2,2,4-三甲基戊烷-1,3-二醇-单异丁酸酯、丁基乙二醇、丁基二乙二醇、丁基二丙二醇、丙二醇丁醚和二丙二醇丁醚。
充当用于调节粘度的试剂的合适的流变添加剂为例如淀粉衍生物和纤维素衍生物和疏水改性的乙氧基化的氨基甲酸酯(HEUR)增稠剂、可碱溶胀的丙烯酸酯增稠剂、疏水改性的丙烯酸酯增稠剂、丙烯酰氨基甲基丙烷磺酸的聚合物，或热解二氧化硅。
常规助剂的概况参见Wernfried Heilen等人于2009年由Vincentz Network发表的“Additive fürLacksysteme”。
本发明的另一个主题是用于减少分散体的水相和固相之间的分离(本领域技术人员通常称为脱水收缩)的方法，这通过将式(I)的化合物和任选的聚结剂、消泡剂、杀生物剂、流变添加剂以及润湿剂和/或分散剂溶解在水中进行。当需要颜料时，以高剪切分散引入颜料。然后使所获得的组合物与聚合物粘结剂和任选地与其它助剂以低剪切速率进行搅拌。作为分散设备，可以使用搅拌器、溶解器、快速混合器或捏合装置，优选具有锯齿搅拌器的溶解器。上述制备可以在0至100℃，有利地在10至70℃，优选在20至40℃的温度进行。
式(I)的化合物优选以0.01％至10％，尤其是0.01％至5.0％，特别是0.01％至1.0％的浓度存在。
此外还可以利用所述方法调节pH值。为此，可以在一开始或分散过程和配制过程中在分散体中加入足够量的式(I)的化合物，从而获得7和11之间的pH值。
根据本发明的分散体的一个特别性能是式(I)的化合物对整体配制的无VOC且无味的贡献。
根据本发明的分散体适合制备所有类型的涂料。根据本发明的分散体特别适合制备刷抹料油漆和分散体油漆、分散体清漆、粘着剂。
实施例
如果没有另外说明，本说明书中的百分比数据为基于总组合物重量的重量百分比。
乙酸乙烯酯-VeoVa-丙烯酸酯油漆形式的实施例1-5(对比实施例)和实施例6-7：
在对比系列中，含氨溶液和市售胺二乙醇胺(DEA)、三乙醇胺(TEA)、环己基二乙醇胺CH-020，Clariant)和2-氨基-2-甲基-1-丙醇(AMP-95，Dow)与N-甲基葡糖胺(NMG)和二甲基葡糖胺(DMG)进行对比。所使用的油漆的组成如下，其中使用等摩尔量的胺：
表1：乙酸乙烯酯-VeoVa-丙烯酸酯油漆的以重量％计的组成
在室温下依次加入组分1-14，借助于Getzmann公司的具有锯齿搅拌器的溶解器以高剪切速率进行分散。然后以低剪切速率搅拌引入组分15-18。
苯乙烯-丙烯酸酯油漆形式的实施例8-12(对比实施例)和实施例13-14：
表2：苯乙烯-丙烯酸酯油漆的以重量％计的组成
依次加入组分1-14，以高剪切速率进行分散。然后以低剪切速率搅拌引入组分15-18。
评价pH值、粘度、冻融稳定性和湿磨损从而评价油漆。为了模拟储存稳定性，在60℃下储存油漆一周，并且评价脱水收缩、pH值和粘度。如下确定所述参数。
在油漆配制之后并且在60℃下1周之后经由Knick公司的pH电极(SE 100N)确定pH值。
通过ThermoScientific的Haake Viscotester 550确定粘度。
根据标准DIN EN ISO 11998和DIN EN 13300在200μm油漆膜上在室温干燥1周之后确定耐湿磨损性。
为了确定冻融稳定性，在-18℃下冷冻油漆样品然后再次融化。重复足够长的时间，直至不能观察到永久性损坏。评价冻融稳定周期的数目。
为了确定脱水收缩，在具有料位刻度的容器中填充相同量的油漆。然后在60℃下储存1周之后读取分离的水量并且记录为油漆量的百分比。
发现通过加入胺在所有情况下获得pH值为8至10的油漆。此外表3和4中的结果表明，油漆具有粘度、湿磨损和冻融稳定性方面的相当的性能特性。关于脱水收缩观察到NMG和DMG相对于对比胺显著减少了脱水收缩。
对于0.1％至15％的VOC含量根据DIN EN ISO 17895测定胺的VOC含量，对于0.01％至0.1％的VOC含量根据DIN EN ISO 11890-2测定胺的VOC含量。以鼻嗅方式在样品上测定气味。表5中汇总了对比胺氨、单乙醇胺(MEA)、DEA、TEA、AMP-95和CH-020以及根据本发明的胺NMG和DMG的VOC含量和气味。
表5：所描述的胺的气味和VOC含量

Claims (20)

1.分散体，所述分散体包含
(A)至少一种式(I)的化合物
其中R1表示H、C1-C4-烷基、CH2CH2OH或CH2CH(CH3)OH，
(B)聚合物粘结剂
和
(C)水。
2.根据权利要求1所述的分散体，所述分散体还包含一种或多种选自如下的成分：颜料、分散剂、消泡剂、聚结剂、流变添加剂、杀生物剂、润湿剂。
3.根据权利要求1和/或2所述的分散体，其中R1为H、甲基或CH2CH2OH。
4.根据权利要求1和/或2所述的分散体，其中R1为H或甲基。
5.根据权利要求1至4中任一项或多项所述的分散体，其中式(I)的化合物的浓度为0.01至10重量％。
6.根据权利要求1至4中任一项或多项所述的分散体，其中式(I)的化合物的浓度为0.01至5％。
7.根据权利要求1至4中任一项或多项所述的分散体，其中式(I)的化合物的浓度为0.01至1％。
8.根据权利要求1至7中任一项或多项所述的分散体，所述分散体包含10至80重量％的量的白色颜料或彩色颜料。
9.根据权利要求1至8中任一项或多项所述的分散体，所述分散体包含0.01至10重量％的量的润湿剂或分散剂。
10.根据权利要求1至9中任一项或多项所述的分散体，所述分散体包含0.01至5重量％的量的消泡剂。
11.根据权利要求1至10中任一项或多项所述的分散体，所述分散体包含0.01至5重量％的量的杀生物剂。
12.根据权利要求1至11中任一项或多项所述的分散体，所述分散体包含0至5重量％的量的聚结剂。
13.根据权利要求1至12中任一项或多项所述的分散体，所述分散体包含0.1至10重量％的量的流变添加剂。
14.根据权利要求1至13中任一项或多项所述的分散体，其中包含1至80重量％的成分B)。
15.根据权利要求1至14中任一项或多项所述的分散体，其中包含1至80重量％的水。
16.根据权利要求1至15中任一项或多项所述的分散体，其中式(I)的化合物源自葡萄糖。
17.式(I)的化合物在分散体中作为表面活性成分的用途，所述分散体包含至少一种聚合物粘结剂和水，
其中R1表示H、C1-C4-烷基、CH2CH2OH或CH2CH(CH3)OH。
18.用于减少分散体的水相和固相之间的分离的方法，通过将式(I)的化合物和任选的聚结剂、消泡剂、杀生物剂、流变添加剂以及润湿剂和/或分散剂溶解在水中，然后在低剪切速率下搅拌引入聚合物粘结剂而进行。
19.根据权利要求18所述的方法，所述方法在0至100℃的温度进行。
20.根据权利要求18和/或19所述的方法，其中向式(I)的化合物和任选的聚结剂、消泡剂、杀生物剂、流变添加剂以及润湿剂和/或分散剂的溶液中添加至少一种颜料，并且在高剪切下分散该组合物。
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RU2017107735A3 (zh) 2018-09-13
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DE102014012020A1 (de) 2016-02-18
KR20170041866A (ko) 2017-04-17
CN106574132B (zh) 2018-11-30
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