CN102304212A - 用于生产含水1k-pur涂料的水可稀释性或水溶性的封端型多异氰酸酯 - Google Patents
用于生产含水1k-pur涂料的水可稀释性或水溶性的封端型多异氰酸酯 Download PDFInfo
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- CN102304212A CN102304212A CN2011101547816A CN201110154781A CN102304212A CN 102304212 A CN102304212 A CN 102304212A CN 2011101547816 A CN2011101547816 A CN 2011101547816A CN 201110154781 A CN201110154781 A CN 201110154781A CN 102304212 A CN102304212 A CN 102304212A
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- 230000000087 stabilizing effect Effects 0.000 description 1
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- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
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- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
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- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
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- 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
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- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
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- 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
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- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
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- 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
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Abstract
本发明涉及用于生产具有快速物理初始干燥的含水1K-PUR涂料的水可稀释性或水溶性的封端型多异氰酸酯。具体地,本发明涉及新的水可稀释性或水溶性的封端型多异氰酸酯,其容许制备可烘焙的单组分(1K)聚氨酯漆料,该漆料显示快速的物理初始干燥,其具有降低的热发黄性且其获得无浊度的涂层,以及制备它们的方法,和它们的用途。
Description
本申请是申请日为2008年2月21日的中国专利申请号200780030698.X,标题为“用于生产具有快速物理初始干燥的含水1K-PUR涂料的水可稀释性或水溶性的封端型多异氰酸酯”的分案申请。
技术领域
本发明涉及新的水可稀释性或水溶性封端型多异氰酸酯,其容许制备可烘焙的单组分聚氨酯漆料,该漆料显示快速的物理初始干燥,其具有降低的热发黄特型且获得无浊度的涂层,以及制备它们的方法,和它们的用途。
背景技术
基材越来越多地采用含水粘合剂、更特别地具有封端异氰酸酯基团的聚氨酯(PUR)分散体来进行涂覆。含水PUR分散体的制备和涂覆及烘焙方法原则上是现有技术中已知的。
但是,其交联剂组分基本上由封端多异氰酸酯(BNCO交联剂,交联剂分散体)组成的含水单组分聚氨酯烘焙漆料显示在施加涂料之后缓慢的物理初始干燥。这点在将涂覆的对象运送到烘焙炉(其中发生化学交联)时产生问题。该对象可能,例如,粘住传送带或手套。由此在烘焙过程之前需要长的干燥时间段。
另外,具有封端异氰酸酯基团的单组分聚氨酯烘焙漆料显示在高烘焙温度下和/或长烘焙过程期间、或者在过烘焙时发黄的显著趋势。
与具有封端异氰酸酯基团的单组分聚氨酯烘焙漆料的处理相关的另一问题是,经常发生漆膜的浊度,出于获得透明涂覆体系的目的,其特别地阻止了透明基材(如玻璃)的涂覆。
EP-A 0802210描述了具有封端异氰酸酯基团的水可稀释性多异氰酸酯交联剂。为了防止热发黄的问题,提出了使用带有酰肼基团的化合物。依据EP-A 0807650,使用这种类型的多异氰酸酯交联剂涂覆玻璃获得了不发黄的透明膜,但是该体系的物理初始干燥行为非常缓慢且由此是不利的。
非水聚氨酯体系的领域中公知的是利用内酰胺将多异氰酸酯混合封端,且描述于例如DE-A 10156897、DE-A 4416750、EP-A 0403044、DE-A 3128743和US 5455374。但是,通过使用基于内酰胺的混合封端更特别地在含水PUR体系方面实现降低的发黄或者有利的初始干燥行为的构思仍不可行。
发明内容
由此,本发明的目的是提供水可稀释性或水溶性封端型多异氰酸酯,其是含水分散体的形式,在与多元醇组分混合之后,获得可烘焙的单组分聚氨酯漆料,该漆料具有施用之后快速的物理初始干燥且在烘焙时、甚至在过烘焙时具有低的热发黄性。另一目的是容许采用所获得的涂覆剂无浊度地涂覆基材。
现在令人吃惊地发现,具有由内酰胺和其它封端试剂组成的混合封端的亲水化多异氰酸酯满足这些要求。
本发明提供了用于制备具有混合封端的多异氰酸酯预聚物的含水分散体的方法,其中,由下列制备多异氰酸酯预聚物,
a)100当量的至少一种多异氰酸酯组分,
b)10~75当量的一种内酰胺或者多种内酰胺,作为针对异氰酸酯基团的封端剂,
c)2~50当量的不同于b)的针对异氰酸酯基团的其它封端剂,
d)0~15当量的至少一种含有异氰酸酯反应性基团的非离子亲水化试剂,
e)0.5~13当量的至少一种含有异氰酸酯反应性基团的(潜在的)阴离子亲水化试剂,
f)0~30当量的一种或多种无氨基的化合物,其分子量范围为62~250g/mol,含有2~4个OH基团或者至少一个OH基团和其它的对异氰酸酯呈反应性的基团,和
g)0~30当量的一种或多种脂(环)族化合物,其分子量范围为32~300g/mol,含有2~4个氨基或者至少一个氨基和其它的对异氰酸酯呈反应性的基团,
在组分a)~g)彼此之间的反应期间或之后,将该预聚物分散或溶解于水中,和
在分散或溶解步骤之前、期间或之后,采用碱使e)中使用的亲水化试剂的潜在的阴离子基团至少部分地去质子化。
组分b)~g)的当量用量数据与这些组分中存在的化合物的异氰酸酯反应性基团的各自数量相关,a)中使用的异氰酸酯组分具有100当量的可用于反应的游离(frei)NCO基团。
在一种用于制备具有混合封端的多异氰酸酯预聚物的含水分散体的优选实施方式中,使反应物a)~f)彼此反应并随后将产物分散或溶解于水中,在前述步骤之前、期间或之后进行采用碱使e)中使用的亲水化试剂的潜在阴离子基团至少部分去质子化。任选添加的组分g)优选地在已将预聚物分散于水中之后进行添加。
一种特别优选的实施方案中,首先,使组分a)与组分d)、e)和f)反应,之后进行与组分b)且随后与组分c)的反应。随后加入碱用于去质子化,并使反应混合物分散于水中。最后,可以加入组分g)。
优选地选择反应物的数量比例,使得异氰酸酯组分a)与组分b)、c)、d)、f)和g)的对异氰酸酯呈反应性的基团的当量比为1∶0.7~1∶1.3、优选为1∶0.85~1∶1.1。这种当量比的计算既不包括组分e)的酸基团也不包括用于制备聚氨酯的溶液或分散体的水或溶剂,也不包括用于使酸基团去质子化的去质子化试剂。
用于组分a)的适宜多异氰酸酯为本领域技术人员已知的NCO官能化合物,具有优选2或更多的官能度。这些典型地为脂族、脂环族、芳脂族和/或芳族二异氰酸酯或三异氰酸酯,以及它们具有亚氨基氧杂二嗪二酮、异氰脲酸酯、异氰酸酯二聚体、氨基甲酸酯、脲基甲酸酯、缩二脲、脲、氧杂二嗪三酮、唑烷酮、酰基脲和/或碳二亚胺结构的更高分子量的衍生物(其含有两个或更多个游离NCO基团)。
该二异氰酸酯或三异氰酸酯的实例为四亚甲基二异氰酸酯、环己烷-1,3-和-1,4-二异氰酸酯、六亚甲基二异氰酸酯(HDI)、1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷(异佛尔酮二异氰酸酯,IPDI)、亚甲基双(4-异氰酸酯根合环己烷)、四甲基亚二甲苯基二异氰酸酯(TMXDI)、三异氰酸根合壬烷、亚甲苯基二异氰酸酯(TDI)、二苯基甲烷-2,4’-和/或4,4’-二异氰酸酯(MDI)、三苯基甲烷4,4’-二异氰酸酯、亚萘基-1,5-二异氰酸酯、4-异氰酸根合甲基-1,8-辛烷二异氰酸酯(壬烷三异氰酸酯,三异氰酸根合壬烷,TIN)、和/或十一烷-1,6,11-三异氰酸酯,以及其任意的混合物,以及任选地其它二-、三-和/或多异氰酸酯的混合物。
该多异氰酸酯典型地具有0.5~60重量%、优选3~30重量%、更优选5~25重量%的异氰酸酯含量。
本发明的方法中,优选使用具有异氰脲酸酯、氨基甲酸酯、脲基甲酸酯、缩二脲、亚氨基氧杂二嗪二酮、氧杂二嗪三酮和/或异氰酸酯二聚体基团且基于脂族和/或脂环族二异氰酸酯的更高分子量的化合物。
本发明的方法中,特别优选地在组分a)中使用具有缩二脲、亚氨基氧杂二嗪二酮、异氰脲酸酯和/或异氰酸酯二聚体基团且基于六亚甲基二异氰酸酯、异佛尔酮二异氰酸酯和/或4,4’-二异氰酸根合二环己基甲烷的化合物。
非常特别优选地使用具有异氰脲酸酯结构且基于异佛尔酮二异氰酸酯的多异氰酸酯。
使用的组分b)的封端剂是具有酰胺H原子的内酰胺(环状酰胺)。实例为λ-丁内酰胺(2-吡咯烷酮)、δ-戊内酰胺和/或ε-己内酰胺;优选ε-己内酰胺。组分b)的用量优选为30~65当量,基于异氰酸酯组分a)的NCO基团。
作为组分c),能够使用本领域中本身已知的用于异氰酸酯基团的封端的单官能封端剂,其并不存在于组分b)中。实例为酚类,肟类如丁酮肟、丙酮肟或环己酮肟,胺类如N-叔丁基苄基胺或二异丙基胺,3,5-二甲基吡唑,***,含有可去质子化基团的酯如丙二酸二乙酯、乙酰乙酸乙酯,及其混合物和/或与其它封端剂的混合物。优选丁酮肟、丙酮肟、3,5-二甲基吡唑和/或它们的混合物,特别优选丁酮肟。组分c)的用量优选为10~30当量,基于异氰酸酯组分a)的NCO基团。
亲水化组分d)由至少一种含有异氰酸酯反应性基团的非离子亲水化化合物组成。该化合物的实例为含有至少一个羟基或氨基以及一个或多个氧亚烷基单元(其中至少一个为氧亚乙基单元)的聚氧亚烷基醚。这些聚氧亚烷基醚可以以已知方式通过适宜起始物分子的烷氧基化获得。
适宜的起始物分子为,例如,饱和一元醇如甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、仲丁醇、异构的戊醇、己醇、辛醇和壬醇、正癸醇、正十二烷醇、正十四烷醇、正十六烷醇、正十八烷醇、环己醇、异构的甲基环己醇或羟基甲基环己烷、3-乙基-3-羟基甲基氧杂环丁烷或四氢呋喃醇、二乙二醇单烷基醚如二乙二醇单丁基醚、不饱和醇如烯丙醇、1,1-二甲基烯丙醇或油醇、芳族醇如苯酚、异构的甲苯酚或甲氧基苯酚、芳脂族醇如苄醇、茴香醇或肉桂醇、仲单胺如二甲基胺、二乙基胺、二丙基胺、二异丙基胺、二丁基胺、双(2-乙基己基)胺、N-甲基-和N-乙基环己基胺或二环己基胺,以及杂环仲胺如吗啉、吡咯烷、哌啶或1H-吡唑。优选的起始物分子为饱和一元醇。特别优选使用二乙二醇单丁基醚作为起始物分子。
适用于烷氧基化反应的环氧烷烃特别是环氧乙烷(Ethylenoxid)和环氧丙烷(Propylenoxid),其可以以任意顺序或是以混合物形式用于烷氧基化反应。优选将环氧乙烷和环氧丙烷分批加到起始物(Starter)中。
聚环氧烷烃聚醚为纯的聚环氧乙烷聚醚或是混合型聚环氧烷烃聚醚(其环氧烷烃单元的优选至少30mol%、更优选至少40mol%由环氧乙烷单元组成)。优选的非离子化合物为单官能混合型聚环氧烷烃聚醚,其含有至少40mol%的环氧乙烷单元和最多60mol%的环氧丙烷单元。
环氧乙烷单元相对于组分a)~g)的总固体含量的用量为低于30重量%,优选低于20重量%,更优选低于15重量%。
组分d)的用量优选为3~8当量,基于异氰酸酯组分a)的NCO基团。
亲水化组分e)由至少一种具有至少一个对于异氰酸酯基团具有反应性的基团的(潜在的)阴离子化合物组成。
这些化合物优选为含有至少一个、优选一个或两个羟基的羧酸,或该羟基羧酸的盐。适宜的这种酸为,例如,2,2-双(羟基甲基)链烷羧酸如二羟甲基乙酸、2,2-二羟甲基丙酸、2,2-二羟甲基丁酸或2,2-二羟甲基戊酸、二羟基琥珀酸、羟基新戊酸或这些酸的混合物。
作为组分e),优选使用二羟甲基丙酸和/或羟基新戊酸。
游离酸基团、更特别地羧基,表示前述“潜在的阴离子”基团,而通过用碱中和获得的盐类基团、更特别地羧酸盐基团表示如上所述的“阴离子”基团。
组分e)的用量优选为5~9当量,基于异氰酸酯组分a)的NCO基团。这种情形下异氰酸酯反应性基团定义为醇基团;羧酸基团和/或羧酸盐基团并不认为是异氰酸酯反应性基团。
作为增链剂组分f)可以考虑二-、三-和/或多元醇。实例为乙二醇,二-、三-、四乙二醇,1,2-丙二醇,二-、三-、四丙二醇,1,3-丙二醇,1,4-丁二醇,1,3-丁二醇,2,3-丁二醇,1,5-戊二醇,1,6-己二醇,2,2-二甲基-1,3-丙二醇,1,4-二羟基环己烷,1,4-二羟甲基环己烷,1,8-辛二醇,1,10-癸二醇,1,12-十二烷二醇,三羟甲基丙烷,蓖麻油,甘油和/或所述产品的混合物,任选地所述产品与其它二-、三-和/或多元醇的混合物。另外能够采用乙氧基化和/或丙氧基化的二-、三-和/或多元醇,例如,乙氧基化和/或丙氧基化的三羟甲基丙烷、甘油和/或1,6-己二醇。
还可以使用除了至少一个羟基之外还含有一个或多个硫醇基团的化合物,如1,2-羟基乙硫醇(1,2-Hydroxyethanthiol)。
作为组分f),优选使用1,4-丁二醇、1,3-丁二醇、2,2-二甲基-1,3-丙二醇、1,6-己二醇和/或三羟甲基丙烷。
优选在f)中使用分子量为62~200g/mol的前述类型的化合物。
组分f)的用量优选为3~15当量,基于异氰酸酯组分a)的NCO基团。
作为增链剂组分g),能够使用异氰酸酯反应性的有机二胺或多胺如1,2-亚乙基二胺、1,2-和1,3-二氨基丙烷、1,4-二氨基丁烷、1,6-二氨基己烷、异佛尔酮二胺、2,2,4-和2,4,4-三甲基六亚甲基二胺的异构体混合物、2-甲基五亚甲基二胺、二亚乙基三胺、4,4-二氨基二环己基甲烷和/或二甲基亚乙基二胺。
另外,作为组分g)也能够使用除了具有伯氨基之外还具有仲氨基或者除了具有氨基(伯或仲)之外还具有OH基团或SH基团的化合物。
其实例为伯/仲胺,如3-氨基-1-甲基氨基丙烷、3-氨基-1-乙基氨基丙烷、3-氨基-1-环己基氨基丙烷、3-氨基-1-甲基氨基丁烷,链烷醇胺如N-氨基乙基乙醇胺、乙醇胺、二乙醇胺、3-氨基丙醇、1-氨基丙醇、新戊醇胺、N-甲基乙醇胺和/或N-甲基异丙醇胺,和链烷硫醇胺如1-氨基丙硫醇。
作为组分g),优选使用二胺或多胺,如乙二胺、异佛尔酮二胺、1,6-二氨基己烷和/或4,4-二氨基二环己基甲烷。
组分g)中,优选使用分子量为60~300g/mol的前述类型的化合物。
组分g)的用量优选为0~10当量,基于异氰酸酯组分a)的NCO基团。
对于增链也可以使用组分f)和g)的混合物。
除了通过与组分f)和/或g)的反应增链之外,也能够使游离NCO基团与水在例如分散过程中反应,形成胺,此时由此形成的伯氨基又通过与游离NCO基团的反应而被消耗,并发生增链。
在制备本发明的分散体的过程中,也可以一并使用溶剂,和/或也可以将原材料以溶液形式来使用。适宜溶剂的实例为N-甲基吡咯烷酮、N-乙基吡咯烷酮、二甲苯、甲苯、乙酸丁酯、乙酸甲氧基丙酯、丙酮或甲乙酮。
使用与水(部分)混溶的挥发性溶剂(例如丙酮或甲乙酮)时,典型地在水中分散之后通过蒸馏将它们分离出来。该过程也称作丙酮法或淤浆法。优点在于降低了在预聚物制备时的粘度,而在制得的分散体中不存在溶剂。
另一可能性是,在反应消耗掉异氰酸酯基团之后加入溶剂。关于这点,也能够采用质子型溶剂如醇类,用于例如稳定分散体或者改进漆料性能。
通常计算用作分散介质的水的用量,使得获得水中固含量为20~60重量%、优选30~45重量%的分散体。
用于将潜在的阴离子基团转化为它们的阴离子形式的去质子化试剂的实例为碱性化合物例如氢氧化钠、氢氧化钾、氨、伯或仲胺如二异丙醇胺或2-氨基-2-乙基-1-丙醇、叔胺如三乙基胺、二甲基环己基胺、二异丙基环己基胺、二异丙基乙基胺、三乙醇胺、甲基二乙醇胺、N,N-二甲基氨基乙醇或N-甲基吗啉、或它们任意的混合物。
优选的去质子化试剂为叔胺如三乙基胺、二异丙基乙基胺和N,N-二甲基乙醇胺;特别优选N,N-二甲基乙醇胺。
通常计算所用去质子化试剂的用量,使得本发明聚氨酯中存在的羧酸基团的去质子化程度(所用的胺/氢氧化物与存在的酸基团的摩尔比)为至少40%,优选70~130%,更优选90~110%。去质子化可以在分散步骤或者溶解步骤之前、期间或之后进行。但是,优选在加入水之前进行去质子化。
为了促进在预聚物制备时的氨基甲酸酯化,也可以将催化剂加到反应混合物中。适宜的催化剂为,例如,叔胺,锡、锌或铋的化合物,或碱性盐。优选二月桂酸二丁基锡和二辛酸二丁基锡。
本发明另外提供了通过所述方法获得的具有混合封端的多异氰酸酯预聚物的含水分散体,以及其中存在的预聚物本身。
同样,本发明提供了具有混合封端的多异氰酸酯预聚物,其特征在于,它们包括
A)至少一种式(I)的结构单元,
其中,
R1为C1~C3亚烷基,和
R2~R5为氢原子,
B)(潜在的)阴离子亲水化基团,和
C)任选地,一个或多个氧亚乙基单元。
本发明的分散体以及本发明的混合封端的预聚物可以用于制备含水、可烘焙的涂覆剂(Beschichtungsmittel)(烘焙漆料),用于涂覆基材(优选金属、矿物材料、木材、塑料的基材,例如用于工业涂漆,玻璃),在织物的涂覆中,和在汽车涂漆中。
由此,本发明另外提供了本发明的具有混合封端的多异氰酸酯预聚物的分散体在制备涂覆剂中的用途,以及获得的涂覆剂和涂层本身,和配备有该涂层的基材。
对于该涂覆剂的制备,典型地将本发明的分散体与可溶于或可分散于水的多羟基化合物和任选地助剂和添加剂共混。
用于该应用目的的适宜的多羟基化合物,以及关于这种类型的烘焙漆料的生产和施用的进一步详细内容,本身是本领域技术人员公知的。该化合物优选为本身公知的含水或水可稀释性粘合剂,其基于多羟基聚酯、多羟基聚氨酯、多羟基聚醚、聚碳酸酯二醇或者含羟基的聚合物,如本身已知的多羟基聚丙烯酸酯、聚丙烯酸酯聚氨酯和/或聚氨酯聚丙烯酸酯。
典型地将这些化合物进行亲水化改性,例如如在EP-A-0 157 291、EP-A-0 498 156或EP-A-0 427 028中所述那样。
这种类型的多羟基化合物通常具有的羟基值为20~200,优选为50~130mg KOH/g。
本发明的涂覆剂中,除了对于本发明来说必要的分散体之外,还可以一并使用的其它醇反应性化合物,如氨基交联剂树脂如蜜胺树脂和/或脲树脂,用于在烘焙期间额外的交联。同样可以使用其它亲水性多异氰酸酯。
作为助剂和添加剂,可以使用常规物质如颜料、填料、流动控制剂、消泡剂和催化剂。为了改进漆料粘着力,该漆料可以包含商业的常规添加剂,例如,巯基硅烷如3-巯基丙基三甲氧基硅烷,环氧基烷基硅烷(Epoxyalkylsilane)如3-缩水甘油基氧基丙基三乙氧基硅烷,氨基烷基硅烷如3-氨基丙基三乙氧基硅烷,它们的水解产物或这些组分的混合物。
本发明的涂覆剂通过本身已知的方法来制备。
对于涂覆,可以通过刮涂、浸涂、喷涂如压缩空气或无空气喷涂,以及通过静电施用例如高速转钟施用,施用本发明的涂覆剂。干膜层厚可以为例如10~120μm。通过在90~200℃、优选130~190℃、更优选140~180℃的温度范围下烘焙使干燥膜固化。也可以在微波辐射的作用下进行固化。烘焙之前,可以使膜在例如20~90℃的温度下物理干燥。
具体实施方式
实施例
除非相反地指出,所有百分比数据均为重量百分比。
除非相反地指出,所有分析测量均涉及23℃的温度。
所报道的粘度是依据DIN 53019在23℃下使用Anton Paar GermanyGmbH,Ostfildern,DE的旋转粘度计,通过旋转粘度测定法测量的。
NCO含量(除非相反地清除指出),均是依据DIN-EN ISO 11909在体积上测量的。
记录的粒度是通过激光相关能谱法(Laserkorrelationsspektroskopie)测量的(设备:Malvern Zetasizer 1000,Malvern Instr.Limited)。
固含量是通过将经称重的样品在120℃下加热而测量的。在恒重下再次将样品称重以计算固含量。
通过IR光谱法进行游离NCO基团的检测(2260cm-1处的频带)。
通过DIN EN ISO 2409划格试验的方式测量粘着力。
热发黄通过对应于DIN 6174的CIELAB方法测量。
化学品:
Desmodur Z 4470M/X:
脂族多异氰酸酯,基于异佛尔酮二异氰酸酯溶解在乙酸甲氧基丙酯和二甲苯(1/1)的混合物中的70%溶液,异氰酸酯含量约12%,Bayer MaterialScience AG,Leverkusen,DE。
Carbowax 750:
甲氧基聚乙二醇,平均摩尔质量750g/mol,Dow Chemical Company,Stade,DE。
Bayhydrol A 145:
水可稀释性、OH-官能聚丙烯酸酯分散体,在水/溶剂石脑油100/2-丁氧基乙醇中约45%,采用二甲基乙醇胺中和,比例为约45.6∶4∶4∶1.4;OH含量约7.3%,Bayer Material Science AG,Leverkusen,DE。
Bayhydrol VP LS 2239:
水可稀释性、含羟基的聚氨酯分散体,在水/NMP(60∶5)中约35%,OH含量约1.6%,Bayer Material Science AG,Leverkusen,DE。
Bayhydrur VP LS 2240:
基于Desmodur W的亲水化、封端的多异氰酸酯交联剂,在水/MPA/二甲苯(56∶4.5∶4.5)中约35%,NCO含量(封端的)约2.5%,Bayer MaterialScience AG,Leverkusen,DE。
其它化学品从Sigma-Aldrich GmbH,Taufkirchen,DE购得的精细化学品。
实施例1
非本发明的,制备丁酮肟封端的交联剂分散体
使359.0gZ 4470M/X在70℃下在标准搅拌装置中,采用氮气冲洗,依次与4.7g二羟甲基丙酸在9.4g N-甲基吡咯烷酮(NMP)中的溶液、37.5g750和3.39g新戊二醇混合。随后将混合物加热到80℃并搅拌直到达到8.02%(计算值8.27%)的恒定NCO值。使混合物冷却到70℃。随后这样加入71.0g丁酮肟:使得反应容器中温度不超过80℃。随后在80℃下继续搅拌,直到通过IR光谱法不再能检测到NCO基团,之后使混合物冷却到70℃并加入2.50g二甲基乙醇胺。进一步冷却到60℃之后,采用570.8g 25℃的去离子水进行分散。将分散体温度调节到50℃,搅拌1小时并在搅拌下使其冷却到室温。
所获分散体的性能如下:
固含量 35.8%
pH值 8.02
粘度(Haake旋转粘度计,23℃) 60mPas
粒度(激光相关能谱法,LKS) 99nm
实施例2
非本发明的,制备丙酮肟封端的交联剂分散体
使466.66gZ 4470M/X在70℃下在标准搅拌装置中,采用氮气冲洗,与13.1g二羟甲基丙酸在26.2g N-甲基吡咯烷酮(NMP)中的溶液混合。随后将混合物加热到80℃并搅拌直到达到9.12%(计算值9.17%)的NCO值。随后加入48.75g750并使混合物在75℃下搅拌直到达到7.84%(计算值7.87%)的NCO值。使混合物冷却到70℃,并随后这样加入76.0g丙酮肟:使得反应容器中温度不超过80℃。随后在80℃下继续搅拌,直到通过IR光谱法不再能检测到NCO基团,之后使混合物冷却到70℃并加入8.70g二甲基乙醇胺。进一步冷却到60℃之后,采用1548g 25℃的去离子水进行分散。将分散体的温度调节到50℃,搅拌1小时并在搅拌下将其冷却到室温。
所获分散体的性能如下:
固含量 31.4%
pH值 8.14
粘度(Haake旋转粘度计,23℃) 900mPas
粒度(激光相关能谱法,LKS) 45nm
实施例3:
非本发明的,制备己内酰胺封端的交联剂分散体
使359.0gZ 4470M/X在70℃下在标准搅拌装置中,采用氮气冲洗,依次与4.7g二羟甲基丙酸在9.4g N-甲基吡咯烷酮(NMP)中的溶液、37.5g750和3.39g新戊二醇混合。随后将混合物加热到80℃并搅拌直到达到8.02%(计算值8.27%)的恒定NCO值。使混合物冷却到70℃,随后加入92.3gε-己内酰胺。随后在100℃下继续搅拌,直到通过IR光谱法不再能检测到NCO基团,之后使混合物冷却到70℃并加入2.50g二甲基乙醇胺。进一步冷却到60℃之后,采用770.53g 25℃的去离子水进行分散。将分散体温度调节为50℃,搅拌1小时并在搅拌下将其冷却到室温。
所获分散体的性能如下:
固含量 36.5%
pH值 7.75
粘度(Haake旋转粘度计,23℃) 85mPas
粒度(激光相关能谱法,LKS) 82nm
实施例4
本发明的,制备具有混合封端的交联剂分散体
使359.0gZ 4470M/X在70℃下在标准搅拌装置中,采用氮气冲洗,依次与4.7g二羟甲基丙酸在9.4g N-甲基吡咯烷酮(NMP)中的溶液、37.5g750和3.39g新戊二醇混合。随后将混合物加热到80℃并搅拌直到达到8.24%(计算值8.27%)的恒定NCO值。使混合物冷却到70℃。随后加入63.4g ε-己内酰胺。随后在100℃下搅拌,直到达到1.75%(计算值1.76%)的恒定NCO值,冷却到75℃并进行17.4g丁酮肟的添加。进行搅拌,直到通过IR光谱法不再能检测到NCO基团,之后使混合物冷却到70℃并加入250g二甲基乙醇胺。进一步冷却到60℃之后,采用582g25℃的去离子水进行分散。使分散体的温度调节到50℃,搅拌1小时并在搅拌下使其冷却到室温。
所获分散体的性能如下:
固含量 35.9%
pH值 8.55
粘度(Haake旋转粘度计,23℃) 138mPas
粒度(激光相关能谱法,LKS) 87nm
实施例5:
本发明的,制备具有混合封端的交联剂分散体
重复实施例4中所述的过程,但是使用74.7g ε-己内酰胺和8.7g丁酮肟作为封端剂。
所获分散体的性能如下:
固含量 36.9%
pH值 8.07
粘度(Haake旋转粘度计,23℃) 120mPas
粒度(激光相关能谱法,LKS) 88nm
实施例6:
本发明的,制备具有混合封端的交联剂分散体
重复实施例4中所述的过程,但是使用52.1g ε-己内酰胺和26.1g丁酮肟作为封端剂。
所获分散体的性能如下:
固含量 36.3%
pH值 8.62
粘度(Haake旋转粘度计,23℃) 113mPas
粒度(激光相关能谱法,LKS) 86nm
实施例7:
本发明的,制备具有混合封端的交联剂分散体
重复实施例4中所述的过程,但是使用19.2g 3,5-二甲基吡唑代替丁酮肟作为封端剂。
所获分散体的性能如下:
固含量 36.2%
pH值 8.4
粘度(Haake旋转粘度计,23℃) 160mPas
粒度(激光相关能谱法,LKS) 97nm
实施例8:
本发明的,制备具有混合封端的交联剂分散体
重复实施例4中所述的过程,但是使用55.4g δ-戊内酰胺(代替ε-己内酰胺)和17.4g丁酮肟作为封端剂。
所获分散体的性能如下:
固含量 36.8%
pH值 7.8
粘度(Haake旋转粘度计,23℃) 100mPas
粒度(激光相关能谱法,LKS) 93nm
为了测量应用技术数据,依据表1配制实施例9~18的漆料共混物,施用并固化。性能数据示于表2中。
表1
通过将封端多异氰酸酯与多元醇组分以它们的当量重量比(BNCO∶OH 1∶1)混合,制得清漆9~18。为了改进漆料粘着力,所述漆料包含商业上常用的添加剂(1.1%,以固体粘合剂计算)。
采用Deka刮刀(第120号刮刀)将上述清漆施用到从Schlier & Hennes获得的3mm厚玻璃片上,并在循环空气炉中170℃下烘焙30分钟。这样获得厚度为约25~30μm的干燥膜。
表2
发现如下漆料技术性能:
*评价:0=好,5=差
试验方法的说明
a)耐溶剂性
为了测量耐溶剂性,将浸透溶剂的棉垫置于经涂覆的基材上并覆盖钟表壳玻璃。暴露时间之后,除去棉垫和可能的溶剂残留物并通过目测评定漆料表面的等级。
b)耐受氢氧化钠水溶液的性能
为了测量耐受氢氧化钠水溶液的性能,将待研究的基材垂直地一半地浸渍到含有5%氢氧化钠水溶液的槽中,覆盖并在70℃下加热8h。随后将板用去离子水冲洗并通过目测评定等级。
c)物理初始干燥
对于物理初始干燥的研究,采用Deka刮刀(第120号刮刀)将相应的清漆施用到从Schlier & Hennes获得的3mm厚玻璃片上,在80℃下进行初步干燥3分钟并随后观察其粘性的消失(0=无粘性~5=高粘性)。
d)膜起雾性
烘焙之后目测评价漆膜的起雾现象(0=未发现~5=强烈起雾)。
关于各种技术性能的要求
a)粘着性:最大1
b)摆锤硬度:最小大于140,更好地大于150
c)耐溶剂性:每个值最大为2
d)耐受NaOH性能:最大1
e)发黄:小于2.0,更好地小于1.0
f)物理初始干燥:最大2
g)膜起雾性:最大1
结果评价:
对于非本发明的自交联烘焙体系,采用现有技术交联剂分散体不能够在物理初始干燥、低热发黄性和膜中不发生起雾方面获得充分的性能组合(实施例9~12)。甚至实施例13中所示两种非本发明的交联剂分散体的共混物(实施例1:肟封端的,实施例3:内酰胺封端的)在自交联分散体的制备中也未获得可接受的涂料。
只有采用本发明的交联剂分散体时,与内酰胺和与其它封端剂反应(实施例14~18),能够获得关键性能的最佳组合(Profil)。另外其它漆料性能,如漆膜的硬度、耐溶剂性和耐受氢氧化钠水溶液性能,符合对高品质涂料体系实行的要求。
Claims (7)
1.用于制备具有混合封端的多异氰酸酯预聚物的含水分散体的方法,其中,由下列制备多异氰酸酯预聚物,
a)100当量的至少一种多异氰酸酯组分,
b)10~75当量的一种内酰胺或者多种内酰胺,作为针对异氰酸酯基团的封端剂,
c)2~50当量的不同于b)的其它的针对异氰酸酯基团的封端剂,
d)0~15当量的至少一种含有异氰酸酯反应性基团的非离子亲水化试剂,
e)0.5~13当量的至少一种含有异氰酸酯反应性基团的(潜在的)阴离子亲水化试剂,
f)0~30当量的一种或多种无氨基的化合物,其分子量范围为62~250g/mol,其含有2~4个OH基团或者含有至少一个OH基团和其它的异氰酸酯反应性基团,和
g)0~30当量的一种或多种脂(环)族化合物,其分子量范围为32~300g/mol,其含有2~4个氨基或者含有至少一个氨基和其它的异氰酸酯反应性基团,
在组分a)~g)彼此之间的反应期间或之后,将该预聚物分散或溶解于水中,和
在分散或溶解步骤之前、期间或之后,采用碱使e)中使用的亲水化试剂的潜在的阴离子基团至少部分地去质子化。
2.权利要求1的用于制备具有混合封端的多异氰酸酯预聚物的含水分散体的方法,其特征在于,组分a)中,使用基于六亚甲基二异氰酸酯、异佛尔酮二异氰酸酯和/或4,4’-二异氰酸根合二环己基甲烷的多异氰酸酯。
3.权利要求1或2的用于制备具有混合封端的多异氰酸酯预聚物的含水分散体的方法,其特征在于,组分b)中,使用ε-己内酰胺作为封端剂。
4.权利要求1~3中任一项的用于制备具有混合封端的多异氰酸酯预聚物的含水分散体的方法,其特征在于,组分c)中,使用丁酮肟、丙酮肟、3,5-二甲基吡唑和/或它们的混合物作为封端剂。
5.权利要求1~4中任一项的用于制备具有混合封端的多异氰酸酯预聚物的含水分散体的方法,其特征在于,异氰酸酯组分a)与组分b)、c)、d)、f)和g)的对异氰酸酯呈反应性的基团的当量比为1∶0.7~1∶1.3。
6.可通过权利要求1~5中任一项的方法获得的具有混合封端的多异氰酸酯预聚物的含水分散体。
7.权利要求6的分散体在制备含水涂覆剂中的用途。
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CNA200780030698XA Pending CN101506262A (zh) | 2006-08-18 | 2007-08-08 | 用于生产具有快速物理初始干燥的含水1k-pur涂料的水可稀释性或水溶性的封端型多异氰酸酯 |
CN2011101547816A Pending CN102304212A (zh) | 2006-08-18 | 2007-08-08 | 用于生产含水1k-pur涂料的水可稀释性或水溶性的封端型多异氰酸酯 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
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CNA200780030698XA Pending CN101506262A (zh) | 2006-08-18 | 2007-08-08 | 用于生产具有快速物理初始干燥的含水1k-pur涂料的水可稀释性或水溶性的封端型多异氰酸酯 |
Country Status (7)
Country | Link |
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US (2) | US20080045641A1 (zh) |
EP (1) | EP2054456B1 (zh) |
JP (1) | JP2010501040A (zh) |
CN (2) | CN101506262A (zh) |
AT (1) | ATE501190T1 (zh) |
DE (2) | DE102006038941A1 (zh) |
WO (1) | WO2008019781A1 (zh) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2691431B1 (en) * | 2011-03-29 | 2017-06-21 | Covestro Deutschland AG | Use of an aqueous preparation for the coating of wood surfaces to achieve a natural-touch effect |
JP5862353B2 (ja) * | 2011-08-05 | 2016-02-16 | 東京エレクトロン株式会社 | 半導体装置の製造方法 |
US10450480B2 (en) * | 2013-03-13 | 2019-10-22 | Hentzen Coatings, Inc. | Water-reducible single-component moisture-curing polyurethane coatings |
US10584220B2 (en) * | 2016-02-26 | 2020-03-10 | Fina Technology, Inc. | Modified polymers and stable emulsions comprising the same |
JP7287795B2 (ja) * | 2019-03-07 | 2023-06-06 | 旭化成株式会社 | ブロックポリイソシアネート組成物、水系塗料組成物及び塗膜 |
CN111234168B (zh) * | 2020-03-05 | 2021-09-10 | 合肥安利聚氨酯新材料有限公司 | 非离子型中和剂及其制备方法、水性聚氨酯及其制备方法和应用 |
EP3875512A1 (de) * | 2020-03-05 | 2021-09-08 | Covestro Deutschland AG | Nicht-ionisch hydrophilierte vernetzerdispersion mit thermolatent gebundenen urethan/harnstoffgruppen |
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US5455297A (en) * | 1992-04-24 | 1995-10-03 | Bayer Aktiengesellschaft | Water-based coating compositions and their use for the production of flexible coatings |
US20020061999A1 (en) * | 2000-09-27 | 2002-05-23 | Degussa Ag | Pulverulent, water-dispersible, blocked polyisocyanate adducts, a process for the preparation and their use |
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JPS5790060A (en) | 1980-07-22 | 1982-06-04 | Takeda Chem Ind Ltd | Powdered coat composition |
GB8913859D0 (en) | 1989-06-16 | 1989-08-02 | Hunter Douglas Ind Bv | Blocked isocyanates and their production and use |
DE3936288A1 (de) * | 1989-11-01 | 1991-05-02 | Bayer Ag | In wasser dispergierbare bindemittelkombinationen, ein verfahren zur herstellung eines einbrennfuellers und dessen verwendung |
DE4101697A1 (de) * | 1991-01-22 | 1992-07-23 | Bayer Ag | Waessrige polyester fuer festkoerperreiche einbrennlacke |
DE4221924A1 (de) * | 1992-07-03 | 1994-01-13 | Bayer Ag | In Wasser lösliche oder dispergierbare Polyisocyanatgemische und ihre Verwendung in Einbrennlacken |
EP0584801A3 (en) * | 1992-08-26 | 1994-09-14 | Mitsubishi Chem Ind | Aromatic polycarbonate resins and process for the preparation thereof |
US5455374A (en) | 1993-06-30 | 1995-10-03 | Bayer Corporation | Liquification of trans, trans-4,4'-diisocyanate dicyclohexylmethane by partially reacting the isocyanate groups with blocking agents |
DE4416750A1 (de) * | 1994-05-13 | 1995-11-16 | Bayer Ag | Mischblockierte Polyisocyanate |
DE19615116A1 (de) * | 1996-04-17 | 1997-10-23 | Bayer Ag | Wäßrige bzw. wasserverdünnbare blockierte Polyisocyanate für die Herstellung von wäßrigen 1K-PUR-Klarlacken mit wesentlich verringerter Thermovergilbung |
DE19619545A1 (de) * | 1996-05-15 | 1997-11-20 | Bayer Ag | Beschichtungsmittel für Glas |
DE19810660A1 (de) * | 1998-03-12 | 1999-09-16 | Bayer Ag | Wäßrige Polyisocyanatvernetzer mit Hydroxypivalinsäure und Dimethylpyrazol-Blockierung |
DE10156897A1 (de) * | 2001-11-20 | 2003-05-28 | Bayer Ag | Mit epsilon-Caprolactam und DIPA bzw. 1,2,4-Triazol mischblockierte Polyisocyanate, deren Herstellung und Verwendung |
-
2006
- 2006-08-18 DE DE102006038941A patent/DE102006038941A1/de not_active Withdrawn
-
2007
- 2007-08-08 AT AT07786611T patent/ATE501190T1/de active
- 2007-08-08 DE DE502007006687T patent/DE502007006687D1/de active Active
- 2007-08-08 WO PCT/EP2007/006988 patent/WO2008019781A1/de active Application Filing
- 2007-08-08 CN CNA200780030698XA patent/CN101506262A/zh active Pending
- 2007-08-08 JP JP2009524929A patent/JP2010501040A/ja not_active Ceased
- 2007-08-08 EP EP07786611A patent/EP2054456B1/de not_active Not-in-force
- 2007-08-08 CN CN2011101547816A patent/CN102304212A/zh active Pending
- 2007-08-14 US US11/891,974 patent/US20080045641A1/en not_active Abandoned
-
2010
- 2010-08-27 US US12/870,175 patent/US20100324214A1/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US5455297A (en) * | 1992-04-24 | 1995-10-03 | Bayer Aktiengesellschaft | Water-based coating compositions and their use for the production of flexible coatings |
US20020061999A1 (en) * | 2000-09-27 | 2002-05-23 | Degussa Ag | Pulverulent, water-dispersible, blocked polyisocyanate adducts, a process for the preparation and their use |
Also Published As
Publication number | Publication date |
---|---|
DE102006038941A1 (de) | 2008-02-21 |
DE502007006687D1 (de) | 2011-04-21 |
WO2008019781A1 (de) | 2008-02-21 |
US20080045641A1 (en) | 2008-02-21 |
ATE501190T1 (de) | 2011-03-15 |
US20100324214A1 (en) | 2010-12-23 |
JP2010501040A (ja) | 2010-01-14 |
EP2054456A1 (de) | 2009-05-06 |
EP2054456B1 (de) | 2011-03-09 |
CN101506262A (zh) | 2009-08-12 |
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