CN1272518A - 制备触变剂的方法及应用 - Google Patents

制备触变剂的方法及应用 Download PDF

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CN1272518A
CN1272518A CN00108188A CN00108188A CN1272518A CN 1272518 A CN1272518 A CN 1272518A CN 00108188 A CN00108188 A CN 00108188A CN 00108188 A CN00108188 A CN 00108188A CN 1272518 A CN1272518 A CN 1272518A
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K·豪本尼斯特尔
U·奥尔斯
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BICC CHEMICAL Co Ltd
BYK Chemie GmbH
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Abstract

本发明涉及一种制备开有效用作触变剂且含有脲尿烷类(ureaurethanes)的溶液的方法,其中单羟基化合物与过量的二异氰酸甲苯酯反应,二异氰酸甲苯酯的未反应部分自反应混合物移除,且所得的单异氰酸酯加成物进一步于锂盐存在下与二胺反应,形成脲尿烷类。本发明亦涉及使用此溶液以赋予涂覆化合物触变性质的应用。

Description

制备触变剂的方法及应用
本发明涉及制备可有效用作触变剂且含脲尿烷类(ureaurethanes)的溶液的方法，其中单羟基化合物与二异氰酸酯反应，且所形成的单异氰酸酯加成物进一步于锂盐存在下于非质子溶剂中与二胺反应，形成脲尿烷类；本发明还涉及此溶液的应用，特别是用于赋予涂覆化合物(诸如，含有溶剂、无溶剂及水性的涂料及漆、PVC增塑溶胶及以环氧化物及不饱和聚酯树脂为基础的涂覆物)触变性质。
为控制液体涂覆化合物的流变学行为，主要使用有机改性的皂土、硅酸、氢化的蒽麻油及聚酰胺蜡。这些物质的缺点是它们一般是干燥的固体，必须以溶剂及剪切力分散，以形成半成品，或必须通过***的温度控制引入到液体涂覆化合物中。如果温度未被保持，则在成品涂覆化合物中产生晶体，造成涂层缺陷。
现今使用的这些流变辅助剂的一般缺点是它们于清晰、透明的涂层内造成混浊及云斑(雾浊)。此外，处理干燥粉末产物于处理期间造成粉尘是非所欲的。
其它有关流变学行为控制的成就被揭示于欧洲专利申请EP-A-0198519。于后者中，异氰酸酯于涂料树脂溶液存在下与胺反应而形成尿素，形成非常细微分散形式的针状结晶。以此方式改性的这些涂料粘合剂以流变控制剂及避免凹陷(sag-preventing)的粘合剂(所谓的“凹陷控制剂”(sag control agents))的形式提供。
这些产物的缺点源自这样的事实，即它们总是结合至用于在其中制备它们的粘合剂上，从而使得成品涂覆剂不能进行任何后续的多方面校正。
欧洲专利EP-B-0006252号描述一种制备触变剂的方法，该方法通过于LiCl存在下使异氰酸酯加成物与聚胺反应而于非质子溶剂中制备脲尿烷类而消除一些上述的缺点。以此方式制备的产物的缺点是，由于制备方法的原因，脲尿烷类的结构未定。虽然异氰酸酯单加成物被描述，事实上，于此情况中并无单加成物(由实施例明显看出)，而只是不同加成物的混合物。于所述方法中，1摩尔的二异氰酸酯先与1摩尔的单醇反应。此方法部分产生所需的NCO-官能基的单加成物，但亦产生无NCO-官能基的加成物。此外，一部分的单体二异氰酸酯保持未反应。
这些不同化合物的比例可依NCO基的可及性(accessibility)及所用的反应条件(诸如，温度及时间)而改变。但是，最大缺点的原因是，以此方式制得的这些所有加成物都含有相当大量的未反应二异氰酸酯，它们于氯化锂存在下与聚胺进一步反应期间，造成脲尿烷类未受控制的链延长，并产生聚合的尿素。这些产物具有沉淀的倾向，且仅能以最大困难度保持于溶液内。
因此，本发明的目的是发现一种产生明确结构的触变剂的方法，结果使以此方式制备的溶液具更大的储存稳定性(超过数个月)及能使产物具更可靠的应用。
出人意外地，发现此问题可由下述方式实现：下述通式(I)的单羟基化合物与1.5倍至5倍的摩尔过量的二异氰酸甲苯酯(toluylenediisocyanate)反应，
         R-OH                 (I)
其中，R是含有4至22个碳原子的正烷基或异烷基、含有6至12个碳原子的环烷基、含有7至12个碳原子的芳烷基或化学式CmH2m+1(O-CnH2n)x-或CmH2m+1(OOC-CvH2v)x-的基团，其中m＝1-22，n＝2-4，x＝1-15且v＝4或5，二异氰酸甲苯酯的未反应部分自反应混合物移除，获得的单异氰酸酯加成物于锂盐存在下与通式(II)的二胺反应，
    H2N-R”-NH2             (II)
其中R”＝-CyH2y，且y＝2-12，及/或与及/或与
Figure A0010818800062
反应，其中R＝CH3-或H。
摩尔过量的二异氰酸甲苯酯优选2-4摩尔，特别优选2-3摩尔。优选地，二异氰酸甲苯酯异构物含有50-80％的2，4-异构物部分。
醇R-OH与部分的可获得的二异氰酸酯反应形成异氰酸酯单加成物的反应完成后，未反应的过量二异氰酸酯自反应混合物移除，优选于温和条件下的真空蒸馏进行。
LiCl或LiNO3(但优选LiNO3)可用作锂盐。以此方式产生的脲尿烷类溶液的固体含量是5-80％，优选20-60％，特别优选25-50％。单加成物与二胺的反应于极性的非质子溶剂内进行，溶剂诸如，例如，二甲基亚砜、N，N-二甲基甲酰胺、N，N-二甲基乙酰胺、N-甲基吡咯烷酮、N-丁基吡咯烷酮或可相当的烷基吡咯烷酮。
相对于使用的二胺的胺当量，锂化合物的量是0.2-2摩尔，优选0.5-1.5摩尔，尤其优选0.75-1.25摩尔锂。
使用LiNO3(相对于LiCl)特别有利，因为氯化物离子对于涂覆化合物具有不利的作用，且促使施用触变涂覆化合物的金属基材的腐蚀。
以此方式制备的脲尿烷类不含有自由的异氰酸酯基或自由的胺基。因此，它们在生理上是安全的。再者，无不利的副反应与粘合剂或填料产生。以此方式制备的这些脲尿烷类溶液的储存稳定性格外高，于一般储存温度自然为6个月或更久。
1.依据EP0006252(非依据本发明)的比较例
将1摩尔(174克)的二异氰酸甲苯酯(65％的2，4-异构物，下称T65)引入反应容器，缓慢滴入1摩尔的丁基三二醇(butyl triglycol)(平均MW 212克)，同时搅拌，用已知方法使反应至终点。于此期间，温度保持低于40℃。以此方式制备的异氰酸酯加成物具有7.3％的自由TDI含量，而总NCO含量是10.9％。此反应混合物加至0.5摩尔的苯二甲胺(68克)及0.75摩尔的LiCl(相对于胺的当量)的N-甲基吡咯烷酮溶液中。固体含量是50重量％。反应放热进行。
以此方式制得的尿素溶液具有形成结晶或于短时间后形成凝胶的倾向。
2.制备单加成物(依据本发明)，实例1-8实例1
将0.5摩尔(37克)的正丁醇于30℃于2小时内添加至1.25摩尔(217.5克)的二异氰酸甲苯酯(80％的2，4-异构物，后称为T80)中。于此期间，温度保持低于45℃。于添加完成后，再搅拌2小时，至达成33.0％的理论NCO含量为止。过量的异氰酸酯于150-170℃的真空(0.1毫巴)蒸馏出。NCO含量是16.9％，而自由TDI含量是＜0.5％。实例2
将0.25摩尔(53g)的正丁基三二醇(羟值：265)于室温于2小时内添加至0.625摩尔(108.75克)的二异氰酸甲苯酯(T65)中。于此期间，实例3
0.3摩尔(47.4克)的1-癸醇于50℃于2小时内添加至0.6摩尔(104.4克)的二异氰酸甲苯酯(T80)中。于此期间，温度保持于50℃及55℃之间。于添加完成后，搅拌持续另外的3小时，至达成24.9％的理论NCO含量为止。过量的异氰酸酯于150-170℃的真空(0.1毫巴)蒸馏出。NCO含量是12.7％，而自由TDI含量是＜0.5％。实例4
0.3摩尔(55.8克)的1-十二醇于50℃于2小时内添加至0.6摩尔(104.4克)的二异氰酸甲苯酯(T80)中。于此期间，温度保持于50及55℃之间。于添加完成后，搅拌持续另外的3小时，至达成23.6％的理论NCO含量为止。过量的异氰酸酯于150-170℃的真空(0.1毫巴)蒸馏出。NCO含量是11.7％，而自由TDI含量是＜0.5％。实例5
0.2摩尔(20克)的环己醇于30℃于2小时内添加至0.8摩尔(139.2克)的二异氰酸甲苯酯(T65)中。于此期间，温度身高并保持于50与55℃之间。于添加完成后，搅拌持续另外的3.5小时，至达成36.9％的理论NCO含量为止。过量的异氰酸酯于150-170℃的真空(0.1毫巴)蒸馏出。NCO含量是15.4％，而自由TDI含量是＜0.5％。实例6
0.25摩尔(50克)的异十三烷醇于40℃于2小时内添加至0.75摩尔(130.5克)的二异氰酸甲苯酯(T65)中。于此期间，温度保持低于60℃。于添加完成后，搅拌持续另外的2小时，至达成29.1％的理论NCO含量为止。过量的异氰酸酯于150-170℃的真空(0.1毫巴)蒸馏出。NCO含量是11.3％，而自由TDI含量是＜0.5％。实例7
0.25摩尔(18克)的丁醇于160℃与0.5摩尔的己内酯(57克)及0.1％(0.075克)的DBTL(二丁基月桂酸锡-dibutyl tinlaurate)反应6小时。然后冷却至50℃。以此方式制备的羟酯(BuCP2)(羟值：186)于40℃于2小时内添加至0.75摩尔(130.5克)的二异氰酸甲苯酯中。期间，温度控制在60℃之下。于添加完成后，搅拌持续另外的2小时，至达成25.5％的理论NCO含量为止。过量的异氰酸酯于150-170℃的真空(0.1毫巴)蒸馏出。NCO含量是8.9％，而自由TDI含量是＜0.5％。实例8
0.2摩尔(70克)的甲氧基聚(乙二醇)350于50℃于2小时内添加至0.6摩尔(104.4克)的二异氰酸甲苯酯(T80)中。于此期间，温度保持于50与55℃之间。于添加完成后，搅拌持续另外的3小时，至达成24.1％的理论NCO含量为止。过量的异氰酸酯于150-170℃的真空(0.1毫巴)蒸馏出。NCO含量是8.0％，而自由TDI含量是＜0.5％。
             表1：单一加成物
  实例     醇     NCO含量     当量    摩尔比例
    1     丁醇     16.9％     248     2.5∶1
    2     丁基三二醇     10.7％     392     2.5∶1
    3     癸醇     12.7％     330     2∶1
    4     十二烷醇     11.7％     358     2∶1
    5     环己醇     15.4％     274     4∶1
    6     异十三烷醇     11.3％     372     2∶1
    7     BuCP2     8.9％     457     3∶1
    8     MPEG350     8.0％     525     3∶1
2.制备脲尿烷(依据本发明)，实例9-16实例9
15.9克的LiCl及68克(0.5摩尔)的苯二甲胺于80℃溶于332克的N-甲基吡咯烷酮，然后于1小时期间添加248克实例1制备的单加成物。于添加完成后，搅拌持续另外的30分钟，然后，冷却至室温。以此方式获得的脲尿烷溶液具有50重量％的固体含量。得到清晰产物，于相当长时间保持稳定而无凝胶形成。实例10
15.9克的LiCl及68克(0.5摩尔)的苯二甲胺于80℃溶于476克的N-甲基吡咯烷酮中，于1小时期间添加386克实例2制备的单加成物。于添加完成后，搅拌持续另外的30分钟，然后，进行冷却至室温。以此方式获得的脲尿烷溶液具有50重量％的固体含量。得到具有长期稳定性的清晰产物。实例11
25.8克的LiNO3及68克(0.5摩尔)的苯二甲胺于80℃溶于424克的二甲基甲酰胺中，于1小时期间添加332克的实例3制备的单加成物。于添加完成后，搅拌持续另外的30分钟，然后，进行冷却至室温。以此方式获得的脲尿烷溶液具有50重量％的固体含量。产物于相当长时期保持清晰。实例12
25.8克的LiNO3及68克(0.5摩尔)的苯二甲胺于80℃溶于839克的二甲基乙酰胺中，于1小时期间添加360克的实例4制备的单加成物。于添加完成后，搅拌持续另外的30分钟，然后，进行冷却至室温。以此方式获得的脲尿烷溶液具有35重量％的固体含量。得到具有长期稳定性的清晰产物。实例13
15.9克的LiCl及84克(0.5摩尔)的六亚甲基二胺于80℃溶于374克的N-甲基吡咯烷酮中，于1小时期间添加274克的实例5制备的单加成物。于添加完成后，搅拌持续另外的30分钟，然后，进行冷却至室温。以此方式获得的脲尿烷溶液具有50重量％的固体含量。得到具有长期稳定性的清晰产物。实例14
12.9克的LiNO3及42克(0.25摩尔)的六亚甲基二胺于80℃溶于361.5克的二甲基甲酰胺中，于1小时期间添加186克的实例6制备的单加成物。于添加完成后，搅拌持续另外的30分钟，然后，进行冷却至室温。以此方式获得的脲尿烷溶液具有40重量％的固体含量。得到具有长期稳定性的清晰产物。实例15
8.0克的LiCl及27.2克(0.2摩尔)的苯二甲胺于80℃被溶于652克的N-甲基吡咯烷酮中，于1小时期间添加191克的实例7制备的单加成物。于添加完成后，搅拌持续另外的30分钟，然后，进行冷却至室温。以此方式获得的脲尿烷溶液具有25重量％的固体含量。得到具有长期稳定性的清晰产物。实例16
9.0克的LiCl及27.2克(0.2摩尔)的苯二甲胺于80℃溶于245克的N-甲基吡咯烷酮中，于1小时期间添加210克的实例8制备的单加成物。于添加完成后，搅拌持续另外的30分钟，然后，进行冷却至室温。以此方式获得的脲烷类溶液具有50重量％的固体含量。得到具有长期稳定性的清晰产物。
            表2：脲尿烷类
  实例编号   产生加成物的实例的编号   二胺   溶剂
    9       1   苯二甲胺   N-甲基吡咯烷酮
    10       2   苯二甲胺   N-甲基吡咯烷酮
    11       3   苯二甲胺   二甲基甲酰胺
    12       4   苯二甲胺   N-甲基吡咯烷酮
    13       5   六亚甲基二胺   N-甲基吡咯烷酮
    14       6   六亚甲基二胺   二甲基甲酰胺
    15       7   苯二甲胺   N-甲基吡咯烷酮
    16       8   苯二甲胺   N-甲基吡咯烷酮
应用实例：
于水、溶液混合物及粘合剂溶液中研究本发明的脲尿烷类形成凝胶的能力。可达成的层厚度进一步于粘合剂内确定。
1∶4的正丁醇/混合二甲苯及3∶1的乙酸正丁酯/甲氧基丙醇溶剂混合物。使用下述粘合剂：
Desmophen VPLS 2009：羟基官能基聚丙烯酯，于乙酸正丁酯内，70％固体(Bayer AG)
Plexigum PQ 610：热塑性聚丙烯酯粉末，溶于乙酸正丁酯内，60％固体(Rohm GmbH)于粘合剂内测试：
1％的脲尿烷溶液搅拌入含有溶剂的粘合剂内，同时剧烈搅拌(Dispermat，2米/秒)。
24小时后，凹陷(sagging)测试于30-300μm施行。为此目的，此混合物以具有可改变膜厚度的手术刀施用。
评估：以μm为单位的凹陷性质(层厚度)于溶剂或水中测试
为研究水中或溶剂中的凝胶强度，脲尿烷类仅经摇动加入水或溶剂中。评估于4小时后进行。
在水中或溶剂混合物中的评估：1＝强凝胶，6＝无凝胶
                               表3：应用结果
   1∶4正丁醇/二甲苯中的凝胶强度   3∶1乙酸丁酯/甲氧基丙醇中的凝胶强度   Desmophem VPLS2009内的层厚度   Plexigum PQ 610内的层厚度
  比较例     3-4       3-4   120μm/些微晶种   90μm/晶种
  实例9     2-3       2   150μm/无晶种   150μm/无晶种
  实例10     2       2-3   180μm/无晶种   150μm/无晶种
  实例11     2       2   150μm/无晶种   180μm/无晶种
  实例12     2       2   150μm/无晶种   210μm/无晶种
  实例13     2-3       2   150μm/无晶种   150μm/无晶种
  实例14     2       2   180μm/无晶种   150μm/无晶种
  实例15     2       2-3   150μm/无晶种   120μm/无晶种
    水中的凝胶强度
  实例16     2       -   150μm/无晶种   -

Claims (7)

1.一种制备可有效用作触变剂且含有脲尿烷类的溶液的方法，其中单羟基化合物与二异氰酸酯反应，形成的单异氰酸酯加成物进一步于锂盐存在下于非质子溶剂中与二胺反应，形成脲尿烷类，其特征在于通式(I)的单羟基化合物与1.5倍至5倍摩尔过量的二异氰酸甲苯酯反应，
              R-OH               (I)
其中，R是含有4至22个碳原子的正烷基或异烷基、含有6至12个碳原子的环烷基、含有7至12个碳原子的芳烷基或化学式CmH2m+1(O-CnH2n)x-或CmH2m+1(OOC-CvH2v)x-的基团，其中m＝1-22，n＝2-4，x＝1-15且v＝4或5，二异氰酸甲苯酯的未反应部分自反应混合物移除，且获得的单异氰酸酯加成物于锂盐存在下与通式(II)的二胺反应，
        H2N-R″-NH2              (II)
其中，R″＝-CyH2y，且y＝2-12，及/或与
Figure A0010818800021
及/或与
Figure A0010818800022
反应，其中R＝CH3-或H。
2.根据权利要求1的方法，其特征在于具有5-80重量％固体含量的溶液被制备。
3.根据权利要求1或2的方法，其特征在于二异氰酸甲苯酯的摩尔过量是2-4摩尔。
4.根据权利要求1至3任一项的方法，其特征在于二异氰酸甲苯酯的异构物混合物是以50-80重量％的2，4-异构物比例使用。
5.根据权利要求1至4任一项的方法，其特征在于相对于二胺的当量，使用0.2-2摩尔的锂化合物。
6.根据权利要求1至5任一项的方法，其特征在于LiNO3用作锂盐。
7.依权利要求1至6任一项的方法制得的溶液用于赋予涂覆化合物触变性质的应用。
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CN1185310C (zh) 2005-01-19
CA2305948A1 (en) 2000-10-29
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DE50000205D1 (de) 2002-07-18
KR20000071860A (ko) 2000-11-25
ES2178621T3 (es) 2003-01-01
DE19919482C2 (de) 2001-04-26
EP1048681A2 (de) 2000-11-02
DK1048681T3 (da) 2002-09-23
ATE219115T1 (de) 2002-06-15
JP4498539B2 (ja) 2010-07-07
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CA2305948C (en) 2008-09-09

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