CN1217971C - 含有烷氧基硅烷结构单元的聚氨酯溶液 - Google Patents
含有烷氧基硅烷结构单元的聚氨酯溶液 Download PDFInfo
- Publication number
- CN1217971C CN1217971C CN008057842A CN00805784A CN1217971C CN 1217971 C CN1217971 C CN 1217971C CN 008057842 A CN008057842 A CN 008057842A CN 00805784 A CN00805784 A CN 00805784A CN 1217971 C CN1217971 C CN 1217971C
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- polyurethane solution
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- alkoxysilane
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- Expired - Lifetime
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- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
本发明涉及含有烷氧基硅烷结构单元的聚氨酯溶液、其制备方法及用途。
Description
本发明涉及含有烷氧基硅烷结构单元的聚氨酯溶液、其制备方法及用途。
聚氨酯溶液是久为人知的,如D.Diederich的《有机化学方法》(Methoden der Organischen Chemie)(Houben-Weyl),卷E20,Georg Thieme Verlag,1997,以及其中引用的文献。
通常,聚氨酯溶液是脂肪族和/或芳香族二或多异氰酸酯与二或三官能的多醇和/或二胺的高分子量反应产物。异氰酸酯官能的化合物与羟基和/或氨基官能的化合物的这种反应进行到接近等当点,以达到所需的高分子量。
为了获得可溶的和易于加工的产品,在达到所需的分子量或聚氨酯溶液的粘度后,必须使链增长反应停止。其实现方法通常是添加低分子量的反应性化合物,如单胺(DE-A 2 633 293)、单异氰酸酯或乙酸酐(DE-A 2 500 921、EP-A 129396),添加反应性单官能的醇如甲醇,或添加其它具有链终止功能的化合物如丁酮肟(DE-A 3 142706)。
在实际工艺中,通常添加某种程度上过量的终止剂,以确保可靠的终止。然而,这种过量会对涂料的性能产生不利影响,这表现在气味公害、渗出、粘合性问题以及由于气泡和形成陷坑而在膜中形成缺陷。这样的溶液的贮存稳定性也会因此受到损害。过量的游离单胺、单异氰酸酯或甚至过量的反应性单醇,由于与聚合物中的尿烷键或酯键的渐进反应,特别是在实际中不可避免的贮存期间,会导致粘度的巨大变化,直至严重的降解现象,连同性能的丧失。
由于聚氨酯溶液通常不再含有反应性端基,因此在施用后只发生物理干燥过程。因此,不可能通过链端的反应性基团进行化学交联,以形成具有改进的性能水平的很高分子量的聚合物。
DE-A 3 401 753公开了具有可用于后交联反应的端芳香族氨基基团的聚氨酯溶液。然而这需要反应物的后续添加。
JP 0 8253 545描述了可交联聚氨酯树脂组合物,其包含具有两个异氰酸酯反应性基团和一个可水解的甲硅烷基基团的化合物。其聚氨酯树脂仅包含侧向键接的甲硅烷基基团。这使交联的粘合剂或涂料具有高硬度,但弹性或延伸率低。具有两个异氰酸酯反应性基团和一个可水解基团的化合物也不适合作为终止剂。
因此,本发明的目的是提供不具有上述缺点的聚氨酯溶液。尤其提供包含高分子量聚氨酯的聚氨酯溶液,其可被可靠地制备和终止,并且,当用于涂料时,不引起任何气味公害、渗出、粘性不足或膜的光学性能不足的问题。并且保证所用终止剂的任何过量不对溶液的贮存稳定性和涂料的性能产生不利影响,同时期望对施工者和工人不产生任何健康危害。
令人惊奇地发现,以结合的形式包含作为终止剂的、具有异氰酸酯反应性基团和至少一个烷氧基硅烷基团的化合物的聚氨酯溶液可以满足上述要求。此外,还令人惊奇地发现,基于本发明的聚氨酯溶液的涂料,具有改进的水解稳定性、很好的粘合性和尤其适意的手感。还令人惊奇地发现,本发明的聚氨酯溶液特别适于制备具有高水蒸汽透过性的、因此具有优异的穿着舒适性的高质量涂料。本发明的涂料兼具高水蒸汽透过性和很好的耐水性或耐湿性和较低的水溶胀性。
以结合的形式包含作为终止剂的、具有异氰酸酯反应性基团和烷氧基硅烷基团的化合物以及少量的其它具有至少两个异氰酸酯反应性基团和至少一个烷氧基硅烷结构单元的化合物的聚氨酯溶液,同样令人惊奇地形成满足上述要求的、并且还同时具有优异的膜机械性能、尤其是高的延伸性和弹性和很高的熔融或软化温度的涂料,这些性能对于许多应用如织物涂料而言是十分有利的。
含有作为终止剂的、具有伯氨基基团和至少一个烷氧基硅烷基团的化合物与马来酸二烷基酯的反应产物(含有天冬氨酸酯结构单元)的聚氨酯溶液,也令人惊奇地满足上述要求,尽管天冬氨酸酯结构单元已知具有降低的反应活性。它们还具有另一优点,即,既可以在很早的反应时间也可以在无有机溶剂的条件下使用较大量的终止剂,而不会有形成微溶或不溶的脲类树脂或凝胶颗粒的危险。此外,另一方面,可以得到除具有优异的膜机械性能之外,还具有优异的、尤其柔软的手感和很高的穿着舒适性的涂料,这些性能对于许多应用而言是很重要的。
本发明因此提供具有烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,其是下述组分的在有机溶液中的反应产物:
a)至少一种至少双官能的多醇,其分子量为500-16,000,
b)至少一种至少双官能的多异氰酸酯,其分子量为140-1,500,
c)至少一种低分子量的至少双官能的醇和/或胺,其分子量为32-500,
d)至少一种含有至少一个烷氧基硅烷基团和异氰酸酯反应性基团的化合物,和
e)任选地,具有氨基、醇或肟基团的单官能的物质,
其中,来自组分d)的终止剂当量是d)和e)的终止剂总量的至少50%。
本发明优选提供具有烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,其是下述组分的在有机溶液中的反应产物:
a)40-92重量%的至少一种至少双官能的多醇,其分子量为500-16,000,
b)7-50重量%的至少一种至少双官能的多异氰酸酯,其分子量为140-1500,
c)0.5-20重量%的至少一种低分子量的至少双官能的醇和/或胺,其分子量为32-500,
d)0.1-5重量%的至少一种含有至少一个烷氧基硅烷基团和异氰酸酯反应性基团的化合物,和
e)任选地,具有氨基、醇或肟基团的单官能的物质,
其中,来自组分d)的终止剂当量是d)和e)的终止剂总量的至少75%。
本发明尤其优选提供聚氨酯溶液,其特征在于,其是下述组分的在溶液中的反应产物:
a)47-88重量%的至少一种至少双官能的多醇,其分子量为500-16,000,
b)10-40重量%的至少一种至少双官能的多异氰酸酯,其分子量为140-1500,
c)0.8-17重量%的至少一种低分子量的至少双官能的醇和/或胺,其分子量为32-500,
d)0.2-3.0重量%的至少一种含有烷氧基硅烷基团和异氰酸酯反应性基团的化合物,和
e)0-0.5重量%的具有氨基、醇或肟基团的单官能的物质,
其中,来自组分d)的终止剂当量是d)和e)的终止剂总量的至少95%。
本发明也提供制备具有烷氧基硅烷结构单元的聚氨酯溶液的方法,其特征在于,首先在一个一或二级反应中由至少一种多醇a)、至少一种双官能的多异氰酸酯b)、任选地共用的低分子量组分c)制备异氰酸酯官能的聚氨酯,然后任选地在另一反应步骤中通过与至少双官能的组分c)反应使分子量进一步增长,并于最后的反应步骤中与至少一种含有烷氧基硅烷基团和异氰酸酯反应性基团的化合物d)和任选地共用的单官能的组分e)进行反应,以得到具有烷氧基硅烷结构单元的、不再含有游离的异氰酸酯基团的高分子量聚氨酯,有机溶剂可以在第一反应步骤之前、期间或之后加入,其量应使形成的具有烷氧基硅烷端基的聚氨酯溶液的固含量为9-65重量%。
本发明也提供含有烷氧基硅烷结构单元的聚氨酯溶液在油漆、涂料、密封剂和/或粘合剂中的用途。
聚氨酯溶液也包括聚氨酯-聚脲溶液,以及除包含氨基甲酸酯和/或脲结构单元之外还包含较少量的如三聚体、脲二酮(uretdione)、脲基甲酸酯和/或缩二脲结构单元的溶液。通常,溶液是澄清的,但是也包括具有混浊或不透明外观的溶液,虽然这是少被优选的。
适于制备本发明的聚氨酯溶液的多醇组分a)是例如聚酯多醇(如,Ullmanns工业化学百科全书(Ullmanns Enzyklopdie dertechnischen Chemie),第四版,第19卷,第62-65页)。制备这类聚酯多醇的适合的原料是双官能的醇,如乙二醇、1,2-和1,3-丙二醇、1,3-、1,4-和2,3-丁二醇、1,6-己二醇、新戊二醇、三甲基己二醇、三甘醇、四甘醇、氢化双酚、三甲基戊二醇、二亚乙基二甘醇、二亚丙基二甘醇、1,4-环己烷二醇和1,4-环己烷二甲醇,和双官能的羧酸或其酸酐,如己二酸、邻苯二甲酸(酐)、间苯二甲酸、马来酸(酐)、对苯二甲酸、四氢邻苯二甲酸(酐)、六氢邻苯二甲酸(酐)、琥珀酸(酐)、富马酸、壬二酸和二聚脂肪酸。也适于以少量共用的聚酯原料是单羧酸如苯甲酸、2-乙基己酸、油酸、豆油脂肪酸、硬脂精脂肪酸、花生油脂肪酸、亚麻子油脂肪酸、壬酸、环己烷单羧酸、异壬酸、山梨酸和conjuene脂肪酸,较高官能度的羧酸或醇如偏苯三酸(酐)、丁烷四羧酸、三聚脂肪酸、三羟甲基丙烷、甘油、季戊四醇、蓖麻油和二季戊四醇,以及其它未列出名称的聚酯原料。
适合的多醇组分a)也可以是聚碳酸酯二醇,其可通过例如二苯基碳酸酯或二甲基碳酸酯与低分子量二醇或三醇或ε-己内酯改性的二醇或三醇的反应制备。
适合的多醇组分a)也可以是羟基官能的硅氧烷或聚硅氧烷,如BaysilonOF(Bayer AG)。
基于内酯的聚酯二醇也是适合的,它们是内酯的均聚物或共聚物,优选含有端羟基基团的、内酯如ε-己内酯或γ-丁内酯对双官能的起始分子的加成产物。适合的起始分子可以是上述二醇,或低分子量聚酯二醇或聚醚二醇。除内酯的聚合物之外,还可以使用相应的羟基羧酸。
适合的多醇组分a)还可以是聚醚多醇。它们可以通过例如环氧乙烷、环氧丙烷和/或四氢呋喃单独地例如在BF3或碱性催化剂的存在下的聚合进行制备,或通过这类化合物、任选地以混合物或依次的方式对具有活性氢原子的起始化合物如醇、胺、氨基醇或水的加成进行制备。
所述多醇组分a)也可以以混合物的形式使用,任选地也与其它多醇a)如聚酯酰胺、聚醚酯、聚丙烯酸酯或基于环氧树脂的多醇混合使用。
多醇a)的羟值是5-350、优选8-200mg KOH/g物质。多醇a)的分子量是500-25,000、优选500-15,000,其中,在一个优选实施方案中,至少部分的具有>9,000g/ml分子量的多醇a)被使用。
优选的组分a)是水解稳定的多醇,其分子量为300-3,500、尤其是900-2,500,尤其包含达到至少50%的聚碳酸酯二醇,其可与四氢呋喃二醇和/或二或三官能的基于环氧丙烷或环氧丙烷/环氧乙烷的聚醚混合使用,或是所述水解稳定的多醇的混合物,其中如果使用了三官能的聚醚多醇,其最大用量基于聚合物的总固含量为最多4重量%。这些水解稳定的多醇也可以与聚酯多醇、优选具有较好的水解稳定性的聚酯多醇一同使用,所述聚酯例如是基于邻苯二甲酸酐、间苯二甲酸、二聚脂肪酸、己二醇和/或新戊二醇的聚酯。
在另一优选的实施方案中,使用亲水性多醇如环氧乙烷聚醚、环氧乙烷/环氧丙烷聚醚或基于三甘醇或四甘醇和二羧酸的聚酯作为组分a),其用量是使由其制备的涂料具有水蒸汽可透过性。因此,聚氨酯优选包含作为组分a)的基于聚氨酯总固含量为10-60重量%的亲水性多醇,以及基于聚氨酯总固含量为23-50重量%的非亲水性多醇,组分a)的总量为不高于聚氨酯总固含量的92重量%。
相应的聚氨酯溶液特别适于制备具有高水蒸汽透过性和与之相关的优异的穿着舒适性的高质量涂料。本发明的涂料兼具高水蒸汽透过性和很好的耐水性或耐湿性和较低的水溶胀性。
亲水性组分-多醇a)和任选地亲水性二醇或二胺d)-的总量为聚氨酯溶液总固含量的10-60、优选地20-45重量%。
组分b)包含至少一种有机的至少双官能的多异氰酸酯,其分子量为140-1500,优选168-500。适合的多异氰酸酯是例如六亚甲基-二异氰酸酯(HDI)、异佛尔酮二异氰酸酯(IPDI)、4,4’-二异氰酸根合-二环己基甲烷(H12MDI)、1,4-丁烷二异氰酸酯、H6-2,4-和/或-2,6-二异氰酸根合-甲苯、六氢二异氰酸根合二甲苯、2,4-或2,6-二异氰酸根合甲苯(TDI)、亚二甲苯基二异氰酸酯和4,4’-二异氰酸根合二苯基甲烷(MDI)。也可以共用本身已知的并且基于所述的以及还有其它具有脲二酮、缩二脲、异氰脲酸酯、亚氨基氧杂二嗪二酮或氨基甲酸酯结构单元的异氰酸酯的多异氰酸酯,但这不是优选的。
优选仅使用脂肪族和/或环脂族二官能的分子量为168-262的异氰酸酯,如异佛尔酮二异氰酸酯和/或六亚甲基二异氰酸酯和/或二异氰酸根合二环己基甲烷(DesmodurW,Bayer AG)和/或H6-2,4-和/或-2,6-二异氰酸根合-甲苯,在此,组分b)尤其优选包含达到至少75重量%的异佛尔酮二异氰酸酯或H6-2,4-和/或-2,6-二异氰酸根合甲苯。
仅使用分子量为174-280的芳香族二异氰酸酯、尤其是2,4-和/或2,6-二异氰酸根合甲苯和/或4,4’-二异氰酸根合二苯基甲烷,也是优选的。
在一个优选的实施方案中,使用含有脲基甲酸酯基团的双官能的异氰酸酯作为组分b)。这类组分的制备是通过二异氰酸酯、优选芳香族二异氰酸酯如MDI或TDI,与具有4-18个碳原子的脂肪族直链单醇如正丁醇、己醇、2-乙基己醇或硬脂醇,任选地使用适合的催化剂如乙酰丙酮锌,在例如40-110℃的温度下反应形成脲基甲酸酯进行的。此处,2分子的二异氰酸酯与1分子的单醇反应生成具有脲基甲酸酯结构单元的二异氰酸酯,也可以生成较高的同系物。也可以在本发明的聚氨酯的形成过程中,就地生成脲基甲酸酯。令人惊奇的是,共用含有脲基甲酸酯基团的二异氰酸酯,使生成的聚氨酯能够制备具有尤其好的耐抗性能如耐溶剂性或耐水性和适意手感的涂料。
组分c)是至少一种分子量为32-500的低分子量化合物,其具有至少两个对异氰酸酯基团具有反应性的基团。这些反应性基团优选是羟基和/或伯或仲氨基基团。
适合的组分c)是例如乙二醇、1,2-和1,3-丙二醇、1,4-丁二醇、新戊二醇、1,6-己二醇、三甲基戊二醇、三羟甲基丙烷、甘油、2mol亚丙基碳酸酯与1mol肼的反应产物、乙二胺、二亚乙基三胺、异佛尔酮二胺、己二胺、丙酮连氮、4,4’-二氨基二环己基甲烷、羟乙基亚乙基二胺、乙醇胺、二乙醇胺、异丙醇胺、二异丙醇胺、N-甲基乙醇胺、氨基甲基丙醇、肼(水合)、丙二胺、二甲基乙二胺、己二酸二酰肼、氨基乙磺酸-2-氨乙基酯、丙烯酸和异佛尔酮二胺或乙二胺的1∶1的反应产物、二羟甲基乙酸、2,2’-二羟甲基丙酸、2,2’-二羟甲基丁酸、2,2’-二羟甲基戊酸、任选含有醚基团的磺酸酯二醇(描述于US-A 4 108 814的类型)、具有一个或两个氨基基团的氨基官能的磺酸酯和N-2-(氨乙基)-3氨基丙基三甲氧基硅烷。
如果在按一级或二级进行的第一反应步骤中共用组分c),则优选使用二羟基官能的化合物,尤其是乙二醇、1,4-丁二醇、1,6-己二醇或含有醚基团的磺酸酯二醇。
如果在第二反应步骤中、优选在加入溶剂之后使用组分c),则优选使用二氨基官能的化合物,尤其是乙二胺、异佛尔酮二胺、4,4’-二氨基二环己基甲烷、肼(水合)、己二酸二酰肼或氨基乙磺酸-2-氨乙基酯。
在一个优选实施方案中,共用含有烷氧基硅烷基团的二氨基官能的组分c)作为链增长剂,其优选用量为最多2重量%。令人惊奇的是,使用较大量的这类组分c),使聚氨酯溶液在用作涂料时导致过高的硬度、过低的延伸性或弹性,尤其是导致在低温下较硬的、冷的和十分不舒适的手感。
在一个优选的实施方案中,使用含有盐基团的上述类型的亲水性双官能的化合物作为任选地与亲水性多醇a)联用的组分c),其用量为2-16重量%、尤其优选2.5-13重量%,以赋予相应的涂料以水蒸汽可透过性。
亲水性组分c)尤其优选与上述亲水性多醇a)联用。从而可以制备具有尤其高水蒸汽透过性的涂料。
在一个优选实施方案中,共用肼(水合)、己二酸二酰肼和/或2mol亚丙基碳酸酯与1mol肼的反应产物作为组分c),其用量为0.1-4.5重量%,优选0.1-1.5重量%。从而可以制备具有特别高的热和变色稳定性的聚氨酯溶液。
适于作为组分d)的烷氧基硅烷是氨基烷基硅氧烷如3-氨基丙基三乙氧基硅烷、3-氨基丙基三甲氧基硅烷、3-氨基丙基三丁氧基硅烷、2-氨基乙基三乙氧基硅烷、2-氨基乙基三甲氧基硅烷、2-氨基乙基三丁氧基硅烷、4-氨基丁基三乙氧基硅烷、4-氨基丁基三甲氧基硅烷,所述烷氧基硅烷与马来酸二烷基酯如马来酸二乙酯、马来酸二甲酯或马来酸二丁酯的反应产物,N-苯基氨基丙基三甲氧基硅烷、双(3-三甲氧基甲硅烷基丙基)胺,其中一个或两个烷氧基基团被烷基基团取代的所述类型的化合物,以及所述烷氧基硅烷的以及还有其它烷氧基硅烷的混合物。
组分d)的用量为0.1-5、优选0.2-3.0、尤其优选0.3-1.3重量%。
在一个优选实施方案中,聚氨酯溶液的固体的-Si-(O-)3结构单元的计算确定的量小于1.2重量%。这样可以制备例如尤其在延伸性和弹性方面具有高的机械性能水平的和具有舒适柔软的手感的织物和革的涂料。这些结构单元的较高含量会使涂料的这些希望的性能有所降低。在一个优选的实施方案中,用量为0.3-1.3重量%的单官能的烷氧基硅烷作为组分d)与0.1-2.0重量%的二氨基官能的烷氧基硅烷组分c)一同使用,其中端烷氧基硅烷基团的量必须为全部结合的烷氧基硅烷基团的至少50重量%。令人惊奇地,相应的聚氨酯溶液同样使涂料满足所述的要求,并且还具有优异的膜机械性能、尤其是高延伸性和弹性,并且同时具有很高的熔融或软化温度,这对于许多应用如织物涂料而言是十分有利的。
另一方面,令人惊奇的是,使用较大量的侧向烷氧基硅烷结构单元,会使涂料显示出大为降低的弹性和可延伸性,和很不舒适的冷的手感。粘合性的降低也因此常常是必然的。
在另一优选的实施方案中,作为组分d)使用的是单氨基官能的烷氧基硅烷与0.5-1.1、优选0.9-1.05当量的马来酸烷基酯的单氨基官能的反应产物,其任选地与二氨基官能的烷氧基硅烷一起使用。
包含作为终止剂的、具有伯氨基基团和至少一个烷氧基硅烷基团的化合物与马来酸二烷基酯的反应产物(含有天冬氨酸酯结构单元)和另外少量的含有烷氧基硅烷结构单元的二氨基官能的化合物的聚氨酯溶液,也特别适于制备高质量涂料。
在本发明的聚氨酯溶液的制备中,任选共用的适合的单官能的封端剂e)可以是例如丁酮肟、环己酮肟、丙酮肟、丙二酸酯、三唑、二甲基吡唑、单官能的胺如二丁胺和二异丙基胺以及单官能的醇如乙醇。如果使用组分e),则优选将组分e)首先加入,而组分d)在其后加入。这样可以确保本发明的聚氨酯溶液中不再包含未反应的组分e)。
含有烷氧基硅烷基团的终止剂d)的用量基于终止剂d)和e)的总量为至少50、优选75、尤其优选至少95重量%。
具有烷氧基硅烷基团的本发明的聚氨酯溶液,实际上在室温至最高75℃的条件下显示出适当的贮存稳定性。在施用后,在室温至200℃、优选在60-160℃进行干燥。
具有烷氧基硅烷基团的本发明的聚氨酯溶液的制备方法是,首先在一个按一或二级进行的反应中由至少一种多醇a)、至少一种双官能的多异氰酸酯b)以及任选地共用的低分子量羟基官能的组分c)制备异氰酸酯官能的聚氨酯,然后任选地在另一反应步骤中通过与至少双官能的组分c)反应,任选地共用含有烷氧基硅烷基团的至少双氨基官能的组分c),使分子量进一步增长,并于最后的反应步骤中与含有烷氧基硅烷基团的单氨基官能的组分d)和任选地共用的单官能的组分e)进行反应,以得到具有烷氧基硅烷端基的、不再含有游离的异氰酸酯基团的高分子量聚氨酯,有机溶剂可以在第一反应步骤之前、期间或之后加入,其量应使形成的具有烷氧基硅烷端基的聚氨酯溶液的固含量为9-65重量%。
在一个方法变化中,所有组分a)、b)和任选地c)的一级反应可以通常在适当溶剂的存在下进行,以制备异氰酸酯官能的高分子量聚氨酯,任选地通过随后添加少量的多异氰酸酯b)和/或低分子量双官能的组分c)来达到需要的粘度和获得要求的性能所必须的分子量,然后通过添加单氨基官能的烷氧基硅烷来进行链终止反应。在该方法变化中,单氨基官能的烷氧基硅烷的优选用量为0.3-1.3重量%。
各组分的反应通常在室温至最高120℃下进行,在制备开始时,反应通常在较高的温度如60-120℃下进行,在链增长至链终止反应过程的末尾,反应在较低的温度如室温至60℃下进行。
各组分的反应可以在添加常规的催化剂如二丁基锡二月桂酸盐、锡2-辛酸盐、二丁基锡氧化物或二氮杂二环壬烷的条件下进行。
用于制备本发明的聚氨酯溶液的适合的溶剂是例如二甲基甲酰胺、二甲基乙酰胺、N-甲基吡咯烷酮、甲乙酮、甲基异丁基酮、环己酮、甲苯、二甲苯、叔丁醇、异丙醇、乙酸乙酯、乙酸丁酯、甲氧基丙醇、丁二醇、甲氧基丙基乙酸酯和异丁醇。溶剂或溶剂混合物的性质、添加量和时间的选择,必须使最终产物或中间物料具有溶解性,使粘度处于可以进行工艺处理的范围,即通常<200,000mPas(23℃),并且使溶剂与聚氨酯的原料的反应在很大程度上被排除。换言之,例如,在聚氨酯的制备过程中,仅当只发生异氰酸酯-胺的反应或以较大速率进行的反应时,才可以使用醇类溶剂。
本发明的聚氨酯溶液的固含量为9-65、优选20-50重量%。
本发明的聚氨酯溶液的粘度为1,000-200,000、优选3,000-80,000mPas(23℃)。
本发明的聚氨酯溶液的分子量可以通过例如凝胶渗透色谱法进行测定。其值为4,000-500,000、优选25,000-250,000g/mol。
在本发明的聚氨酯溶液的制备之前、期间或之后或使用之前或期间,可以添加常规助剂和添加剂,如稳定剂、光稳定剂、流动助剂、消光剂、热稳定剂、脱模剂、抗氧化剂、UV吸收剂、HALS活性化合物、消泡剂、粘合促进剂、抗静电剂、防腐剂和催化剂。
具有烷氧基硅烷结构单元的本发明的聚氨酯溶液,适用于油漆、涂料、密封组合物、印刷油墨和粘合剂。它们可以单独使用,和/或在添加常规助剂物质、添加剂、颜料、填料、增塑剂、溶剂和稀释剂之后使用,和/或与其它聚合物或聚合物溶液或低聚物如聚氨酯溶液、聚脲溶液、聚氨酯-聚脲溶液、共聚物和均聚物溶液、氯化橡胶溶液、硝化纤维溶液、纤维素乙酸/丁酸酯溶液、聚丙烯酸酯溶液、聚醚(溶液)、聚酰胺溶液、聚环氧化物(溶液)、聚酯(溶液)、聚异氰酸酯(溶液)、蜜胺-醛-树脂(溶液)、脲树脂(溶液)、聚丁二烯溶液或聚烯烃溶液结合使用。
适合的应用领域是例如织物涂料、革涂料、仿革涂料、塑料涂料或油漆、金属涂料,木材、衍生木材产品和家具的油漆或涂料,所有类型的矿物基材的涂料和油漆以及道路标志油漆。本发明的聚氨酯溶液可以用作例如底涂层、中间涂层、填料、底漆、面漆、透明漆、单涂层漆、微孔涂料、粘合基、表层涂料、修饰涂层、直接涂层、中间涂层或泡沫涂层。
施用方法可以是任何工业上使用的方法,如倾涂、浸涂、辊涂、辊压、刷涂、喷涂、刀涂或凝聚。
实施例
实施例1
将520g分子量为2,000g/mol的双官能的环氧丙烷聚醚加入带有搅拌、冷却和加热装置的3升反应器,并加热到60℃。然后加入205g 4,4’-MDI(Desmodur 44M,Bayer AG),使混合物在70℃反应直至达到或接近理论的异氰酸酯值。加入182g二甲基甲酰胺,聚合物被溶解。然后,在50℃用30分钟加入39.8g 1,4-丁二醇,随后加入另外的271g二甲基甲酰胺。当达到理论的异氰酸酯值后,加入403g甲乙酮和400g甲苯,并将混合物冷却至30℃。在另一容器中,用15.6g异佛尔酮二胺和104g甲苯制备链增长溶液。将该溶液的60%一次加入异氰酸酯官能的聚氨酯溶液。此处用IR光谱法监测异氰酸酯含量的降低。通过分数次添加少量的链增长溶液(共加入另外15%的链增长溶液),使直接通过粘度测量测定的分子量增长。当粘度达到约16,000mPas时,加入18.6g的3-氨基丙基三乙氧基硅烷与马来酸二乙酯的1∶1的反应产物,使反应终止,并将混合物搅拌直至检测不到任何异氰酸酯基团。从而制备了具有端烷氧基硅烷结构单元的35%的聚氨酯溶液,其粘度为15,000mPas。
在室温下于密闭容器中贮存3个月期间内,粘度保持恒定,在60℃下于密闭容器中贮存4个星期后,粘度为16,000mPas。即,具有适合实际应用的粘度稳定性。
用作涂布膜(膜重45g/m2)的测试得到如下结果:
100%模量:2.1MPa
拉伸强度/断裂伸长率(干基):14.3MPa/790%
拉伸强度/断裂伸长率(湿基):14.0MPa/730%
对乙酸乙酯的体积溶胀:350%
熔点:155℃
这些是例如当产品在织物涂料中用作高质量柔性直接涂层时所要求的典型的膜的值。
对比例2a)
为了对比,重复实验1),但不加终止剂。所得35%的聚氨酯溶液的粘度为13,000mPas。
当在60℃于密闭容器中贮存时,数日后粘度上升很大,以至于无法测量。该溶液不具有符合实际需要的稳定性。
这证明了单氨基官能的烷氧基硅烷作为终止剂的活性。
实施例2b
为了对比,重复实验1),但终止剂的用量增加30%,以确定过量的终止剂对贮存稳定性的影响。所得35%的聚氨酯溶液的粘度为13,000mPas。在60℃于密闭容器中贮存4星期后,测得粘度为14,500mPas。因此该溶液具有符合实际需要的稳定性。
实施例3
将450.5g分子量为1,700g/mol的双官能的己二酸-己二醇-新戊二醇聚酯加入带有搅拌、冷却和加热装置的3升反应器,并加热到70℃。然后加入122.1g异佛尔酮二异氰酸酯(DesmodurI,BayerAG),将混合物在100℃反应直至达到理论的异氰酸酯值。加入604g甲苯,聚合物被溶解,然后将溶液冷却到30℃。紧接着302g异丙醇的加入,用30分钟时间加入在另一容器中用46.8g异佛尔酮二胺、302g异丙醇和250g甲氧基丙醇制备的链增长溶液。加料结束后,观察到粘度显著上升。加料后15分钟,粘度达到20,000mPas(23℃),然后加入6.2g的氨基丙基三乙氧基硅烷,并将混合物搅拌直至检测不到任何异氰酸酯基团。从而制备了具有端烷氧基硅烷结构单元的30%的聚氨酯溶液,其粘度为20,500mPas。
在60℃于密闭容器中贮存4星期后,粘度为22,000mPas。
对比例4
为了对比,重复实验2),但是使用当量量的二丁基胺作为链终止剂。
当在50℃于密闭容器中贮存时,粘度从原来的22,000mPas下降到8,500mPas。这或许可以归因于过量的二丁基胺与多醇的酯键的反应,它使分子量降低,并因此具有降低粘度的作用。
对比例5
为了对比,重复实验2),但是使用当量量的丁酮肟作为链终止剂。这样同样可以制备在60℃贮存稳定的聚氨酯溶液。
为了对比涂料的性能,将实施例3)和对比例5)的聚氨酯溶液制成涂布膜,干燥后进行测试。
膜重为42g/m2。
得到如下结果:
实施例3 对比例5
100%模量: 5.8MPa 4.5MPa
拉伸强度/断裂伸长率 58.3MPa/680% 45.0MPa/450%
(干基):
拉伸强度/断裂伸长率 55.4MPa/660% 35.0MPa/450%
(2星期水解测试后):
对乙酸乙酯的体积溶胀: 350% 450%
熔点: 165℃ 165℃
上述结果说明,本发明的聚氨酯溶液可以制备具有较好的膜机械值、改进的耐水解性和对乙酸乙酯低溶胀的涂料。
实施例6
将270g分子量为2,000g/mol的双官能的亲水性环氧乙烷聚醚、57.9g分子量为2,000g/mol的双官能的脂肪族聚碳酸酯二醇(Desmophen 2020,Bayer AG)、57.9g分子量为2,000g/mol的双官能的四氢呋喃聚醚和52g 1,4-丁二醇加入带有搅拌、冷却和加热装置的3升反应器,并加热到60℃。然后加入203g 4,4’-MDI(Desmodur 44M,Bayer AG)以及748g二甲基甲酰胺和748g甲苯,混合物在70℃反应直至达到需要的粘度。如果在达到目标粘度(23℃下20-30,000mPas)之前,异氰酸酯含量达到0,则随后加入少量的4,4’-MDI和任选地少量的1,4-丁二醇。达到目标粘度后,加入4.5g的3-氨基丙基三甲氧基硅烷,并将混合物搅拌直至异氰酸酯值为0,如果适合,随后必须加入少量的链终止单氨基官能的烷氧基硅烷。从而制备了具有端烷氧基硅烷结构单元的30%的聚氨酯溶液,其粘度为24,000mPas。
在室温下于密闭容器中贮存3个月期间内,粘度保持恒定,在60℃下于密闭容器中贮存4个星期后,测得粘度为24,000mPas。
用作涂布膜的测试得到如下结果:
100%模量:5.4MPa
拉伸强度/断裂伸长率(干基):32.9MPa/590%
拉伸强度/断裂伸长率(湿基):30.7MPa/850%
对乙酸乙酯的体积溶胀:80%
对水的体积溶胀:80%
根据SST的水蒸汽透过性:15,000g/m2/d
水蒸汽透过性是根据下述文献中规定的标准测定的:英国纺织技术协会(British Textile Technology Group)的公告DS 2109 TM1,Manchester,英国。
令人惊奇地,也可以制备特别高质量的具有高的水蒸汽透过性的涂料,这是例如在生产用于服装和卫生领域的水蒸汽可透过性织物材料的高质量柔性直接涂层或表面涂层中所要求的。
实施例7
将450.5g分子量为1,700g/mol的双官能的己二酸-己二醇-新戊二醇聚酯加入带有搅拌、冷却和加热装置的3升反应器,并加热到70℃。然后加入122.1g异佛尔酮二异氰酸酯(Desmodur I,BayerAG),混合物在100℃反应直至达到理论的异氰酸酯值。加入608g甲苯,聚合物被溶解,然后将溶液冷却到30℃。紧接着304g异丙醇的加入,用30分钟时间加入在另一容器中用39.9g异佛尔酮二胺、304g异丙醇、252g甲氧基丙醇和9.0g N-2-(氨乙基)-3-氨基丙基三甲氧基硅烷制备的链增长溶液。加料结束后,观察到粘度显著上升。加料后15分钟,粘度达到22,000mPas(23℃),然后加入6.2g的氨基丙基三甲氧基硅烷,并将混合物搅拌直至检测不到任何异氰酸酯基团。
从而制备了具有端和侧向烷氧基硅烷结构单元的30%的聚氨酯溶液,其粘度为20,500mPas。
用作涂布膜的测试得到如下结果:
100%模量:5.9MPa
拉伸强度/断裂伸长率(干基):51.9MPa/500%
拉伸强度/断裂伸长率(2星期水解测试后):50.7MPa/450%
对乙酸乙酯的体积溶胀:350%
熔点:210℃
如果将这一结果与不含侧向或端烷氧基硅烷、而是以丁酮肟作为终止剂的对比例5)的测试结果进行比较,可以看到,本发明的聚氨酯溶液具有优异的机械性能水平、尤其是优异的耐水解性,尽管使用了聚酯多醇,和大大提高的熔点,这对于某些应用例如在织物涂料领域是尤其有利的。
这样的结果是尤其令人惊奇的,因为用现有技术的聚氨酯溶液不能做到兼具高水平的膜机械性能、尤其是很高的延伸性或弹性和很好的耐水解性以及高的熔点。
Claims (22)
1.具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于其是下述组分的在有机溶液中的反应产物:
a)40-92重量%的至少一种至少双官能的多醇,其分子量为500-16,000,
b)7-50重量%的至少一种至少双官能的多异氰酸酯,其分子量为140-1,500,
c)0.5-20重量%的至少一种低分子量的至少双官能的醇和/或胺,其分子量为32-500,
d)0.1-5重量%的至少一种含有至少一个烷氧基硅烷基团和一个氨基的化合物,和
e)非必要地,具有氨基、醇或肟基团的单官能的物质,
其中,来自组分d)的终止剂当量是d)和e)的终止剂总量的至少50%,且所述终止剂是在反应后加入的。
2.根据权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,来自组分d)的终止剂当量是d)和e)的终止剂总量的至少75%。
3.根据权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,其是下述组分的在有机溶液中的反应产物:
a)47-88重量%的至少一种至少双官能的多醇,其分子量为500-16,000,
b)10-40重量%的至少一种至少双官能的多异氰酸酯,其分子量为140-1,500,
c)0.8-17重量%的至少一种低分子量的至少双官能的醇和/或胺,其分子量为32-500,
d)0.2-3.0重量%的含有烷氧基硅烷基团和一个氨基的化合物,和
e)0-0.5重量%的具有氨基、醇或肟基团的单官能的物质,
其中,来自组分d)的终止剂当量是d)和e)的终止剂总量的至少95%。
4.根据权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,组分a)包含至少50重量%的分子量为900-2,500的聚碳酸酯二醇。
5.根据权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,包含作为组分a)的基于聚氨酯总固含量为10-60重量%的亲水性多醇,以及基于聚氨酯总固含量为23-50重量%的非亲水性多醇,其中,组分a)的总量为不高于聚氨酯总固含量的92重量%。
6.根据权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,包含作为组分b)的含有至少75重量%的异佛尔酮二异氰酸酯的脂肪族或环脂族二异氰酸酯。
7.根据权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,包含作为组分b)的2,4-或2,6-二异氰酸根合甲苯和/或4,4’-二异氰酸根合二苯基甲烷。
8.根据权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,包含作为组分b)的含有脲基甲酸酯基团的二异氰酸酯。
9.根据权利要求1-3中任一项的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,包含作为组分c)的2-16重量%的含有盐基团的亲水性双官能的化合物。
10.根据权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,包含亲水性组分c)和亲水性多醇a)。
11.根据权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,包含作为链增长剂的含有烷氧基硅烷基团的二氨基官能的组分c),其用量最多为2重量%。
12.根据权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,包含作为组分c)的肼或肼水合物、己二酸二酰肼和/或亚丙基碳酸酯与肼以2∶1的摩尔比而得到的反应产物,其用量为0.1-1.5重量%。
13.根据权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,包含0.3-1.3重量%的具有一个氨基和至少一个烷氧基硅烷基团的化合物(d)。
14.根据权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,包含作为组分d)的、单氨基官能的烷氧基硅烷与0.5-1.1当量的马来酸烷基酯的单氨基官能的、含有天冬氨酸酯结构的反应产物。
15.根据权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,聚氨酯溶液的固体中的-Si-(O-)3结构单元的计算确定的量小于1.2重量%。
16.根据权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液,其特征在于,包含作为组分d)的用量为0.3-1.3重量%的单氨基官能的烷氧基硅烷以及0.1-2.0重量%的二氨基官能的烷氧基硅烷组分c),其中端烷氧基硅烷基团的量为全部结合的烷氧基硅烷基团的至少50重量%。
17.制备权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液的方法,其特征在于:首先在一个一或二级反应中由40-92重量%的至少一种多醇a)、7-50重量%的至少一种双官能的多异氰酸酯b)以及非必要地共用的0.5-20重量%的分子量为32-500的低分子量至少双官能的多异氰酸酯组分c)制备异氰酸酯官能的聚氨酯,然后非必要地在另一反应步骤中通过与至少双官能的组分c)反应使分子量进一步增长,并于最后的反应步骤中与至少一种含有烷氧基硅烷基团和一个氨基的化合物d)和非必要地共用的具有氨基、醇或肟基团的单官能的组分e)进行反应,以得到具有烷氧基硅烷结构单元的、不再含有游离的异氰酸酯基团的高分子量聚氨酯,其中有机溶剂在第一反应步骤之前、期间或之后加入,其量使形成的具有烷氧基硅烷端基的聚氨酯溶液的固含量为9-65重量%。
18.制备权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液的方法,其特征在于:非必要地在适当的溶剂存在下进行组分a)、b)和非必要地c)的一级反应,以制备异氰酸酯官能的高分子量聚氨酯,非必要地通过随后添加少量的多异氰酸酯b)和/或分子量为32-500的低分子量双官能的组分c)来达到需要的粘度和获得要求的性能所必须的分子量,然后通过添加单氨基官能的烷氧基硅烷d)来进行链终止反应;其中所述组分
a)为至少一种至少双官能的多醇,其分子量为500-16,000,其量为40-92重量%,
b)为至少一种至少双官能的多异氰酸酯,其分子量为140-1,500,其量为7-50重量%,
c)为至少一种低分子量的至少双官能的醇和/或胺,其分子量为32-500,其量为0.5-20重量%,和
d)为至少一种含有至少一个烷氧基硅烷基团和一个氨基的化合物,其量为0.1-5重量%。
19.权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液用于油漆、涂料、密封剂和/或粘合剂的用途。
20.权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液用于塑料上漆和/或涂布的用途。
21.权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液用于涂布织物和革的用途。
22.权利要求1的具有端烷氧基硅烷结构单元的聚氨酯溶液用于具有水蒸汽可透过性的织物涂料的用途。
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Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8070303B2 (en) * | 2002-08-08 | 2011-12-06 | Reflexite Corporation | Optical structures including polyurea |
US20070020463A1 (en) * | 2004-12-23 | 2007-01-25 | Trainham James A | Flexible polymer coating and coated flexible substrates |
US20040122200A1 (en) * | 2002-12-20 | 2004-06-24 | Roesler Richard R. | Process for the preparation of moisture-curable, polyether urethanes with terminal cyclic urea/reactive silane groups |
EP1502927A1 (de) * | 2003-07-31 | 2005-02-02 | Sika Technology AG | Isocyanatfreie Primerzusammensetzung für Glas und Glaskeramiken |
DE10350481A1 (de) * | 2003-10-29 | 2005-06-16 | Henkel Kgaa | Festigkeitsoptimierte Polymere mit gemischten Oxyalkyleneinheiten |
US20060283115A1 (en) * | 2005-04-27 | 2006-12-21 | Robertson Frederick J | Fiberglass mesh faced cornerbead |
ATE462762T1 (de) * | 2005-06-02 | 2010-04-15 | Dow Global Technologies Inc | Schlagzähmodifizierter strukturklebstoff auf epoxid basis |
DE102005041953A1 (de) * | 2005-09-03 | 2007-03-08 | Bayer Materialscience Ag | Niedrigviskose alkoxysilangruppenaufweisende Prepolymere, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung |
US20070129527A1 (en) * | 2005-12-06 | 2007-06-07 | Griswold Roy M | Silylated polyurethane-polyurea protective coating compositions |
US20090056873A1 (en) * | 2006-01-19 | 2009-03-05 | Basf Se | Polyurethane adhesive comprising silane groups and carbodiimide groups |
JP5260834B2 (ja) * | 2006-01-20 | 2013-08-14 | 三井化学株式会社 | 熱可塑性ポリウレタン樹脂組成物及び透湿性フィルム |
US7732554B2 (en) | 2006-09-21 | 2010-06-08 | Momentive Performance Materials Inc. | Process for preparing a curable silylated polyurethane resin |
DE102006055739A1 (de) * | 2006-11-25 | 2008-05-29 | Bayer Materialscience Ag | Abformmassen |
FR2916969B1 (fr) * | 2007-06-05 | 2009-10-02 | Oreal | Kit comprenant des composes x et y fonctionnalises alcoxysilane. |
EP2248857B1 (en) * | 2008-02-25 | 2013-04-10 | DIC Corporation | Process for producing alcohol soluble urethane resin composition, polyurethane porous body, and moisture permeable film |
EP2095832A1 (de) * | 2008-02-28 | 2009-09-02 | Bayer MaterialScience AG | Polyharnstoff-Systeme und deren Anwendung als postoperative Adhäsionsbarrieren, Filme und Verbundteile. |
DE102008032779A1 (de) * | 2008-07-11 | 2010-01-14 | Bayer Materialscience Ag | Polyurethanharnstoff-Lösungen |
WO2010047195A1 (ja) * | 2008-10-24 | 2010-04-29 | 関西ペイント株式会社 | 塗料組成物及び塗膜形成方法 |
CN101429407B (zh) * | 2008-12-08 | 2011-03-09 | 广州市科霖水性材料有限公司 | 水性聚氨酯丙烯酸复合涂层剂及其制备方法 |
US20110030297A1 (en) | 2009-08-07 | 2011-02-10 | Robertson Frederick J | Cornerbead structure |
EP2298826A1 (de) * | 2009-09-17 | 2011-03-23 | Bayer MaterialScience AG | Hydrophile Polyurethanharnstofflösungen |
DE102010000881A1 (de) * | 2010-01-14 | 2011-07-21 | Henkel AG & Co. KGaA, 40589 | 1K- Kaschierklebstoff mit Silanvernetzung |
US10053597B2 (en) | 2013-01-18 | 2018-08-21 | Basf Se | Acrylic dispersion-based coating compositions |
US10640702B2 (en) * | 2013-08-01 | 2020-05-05 | Covestro Llc | Coated particles and methods for their manufacture and use |
US10195826B2 (en) | 2016-03-11 | 2019-02-05 | Solutia Inc. | Cellulose ester multilayer interlayers |
US10293584B2 (en) | 2016-03-11 | 2019-05-21 | Solutia Inc. | Cellulose ester multilayer interlayers |
US10293585B2 (en) | 2016-03-11 | 2019-05-21 | Solutia Inc. | Cellulose ester multilayer interlayers |
US10293582B2 (en) | 2016-03-11 | 2019-05-21 | Solutia Inc. | Cellulose ester multilayer interlayers |
US10300682B2 (en) | 2016-03-11 | 2019-05-28 | Solutia Inc. | Cellulose ester multilayer interplayers |
US10293583B2 (en) | 2016-03-11 | 2019-05-21 | Solutia Inc. | Cellulose ester multilayer interlayers |
US10293579B2 (en) | 2016-03-11 | 2019-05-21 | Solutia Inc. | Cellulose ester multilayer interlayers |
US10293580B2 (en) | 2016-03-11 | 2019-05-21 | Solutia Inc. | Cellulose ester multilayer interlayers |
CN108485586B (zh) * | 2018-02-09 | 2021-01-05 | 广东普赛达密封粘胶有限公司 | 一种高剪切强度枝状硅烷改性聚氨酯组合物及其制备方法 |
CN115160911B (zh) * | 2022-08-17 | 2023-05-05 | 漳州市恩扬工艺品有限公司 | 一种聚氨酯面漆组合物及其制备方法 |
Family Cites Families (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1015488A (en) * | 1972-02-17 | 1977-08-09 | Seiji Nagahisa | Polyurethane composition |
ZA742665B (en) | 1973-05-08 | 1975-04-30 | Commw Scient Ind Res Org | Amine-modified polyurethane and treatment of textile materials |
DE2500921C3 (de) | 1975-01-11 | 1986-10-23 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Polyurethanlösungen |
DE2550796C3 (de) | 1975-11-12 | 1987-04-16 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von stabilen Dispersionen |
CA1081385A (en) | 1975-11-12 | 1980-07-08 | Bayer Aktiengesellschaft | Process for the preparation of stable dispersions |
DE2627073C2 (de) | 1976-06-16 | 1983-12-29 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von stabilen Dispersionen |
DE3142706A1 (de) | 1981-10-28 | 1983-05-05 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung viskositaetsstabiler polyurethanloesungen |
US4485227A (en) | 1983-06-16 | 1984-11-27 | Howmedica, Inc. | Biocompatible poly-(ether-urethane-urea) and process for its preparation |
US4528873A (en) | 1983-08-30 | 1985-07-16 | Frank Lee | Twist set ratchet wrench |
DE3401753A1 (de) | 1984-01-19 | 1985-08-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polyurethanen, polyurethane mit aromatischen aminoendgruppen und ihre verwendung |
US4582873A (en) * | 1984-05-21 | 1986-04-15 | Ppg Industries, Inc. | Process for producing aqueous dispersions, internally silylated and dispersed polyurethane resins, and surfaces containing same |
US5225512A (en) * | 1991-08-29 | 1993-07-06 | Basf Corporation | Polymer and adhesive composition |
US5554686A (en) * | 1993-08-20 | 1996-09-10 | Minnesota Mining And Manufacturing Company | Room temperature curable silane-terminated polyurethane dispersions |
JP3658787B2 (ja) | 1995-03-14 | 2005-06-08 | 大日本インキ化学工業株式会社 | 架橋性ウレタン樹脂組成物 |
JP3765333B2 (ja) * | 1996-09-05 | 2006-04-12 | 大日本インキ化学工業株式会社 | 合成皮革または人工皮革用架橋性ポリウレタン樹脂組成物 |
US6001946A (en) * | 1996-09-23 | 1999-12-14 | Witco Corporation | Curable silane-encapped compositions having improved performances |
US5866651A (en) * | 1996-10-31 | 1999-02-02 | Minnesota Mining And Manufacturing Company | Hydroxycarbamoylalkoxysilane-based poly(ether-urethane) sealants having improved paint adhesion and laminates prepared therefrom |
US6057415A (en) * | 1998-04-09 | 2000-05-02 | Bayer Corporation | Water dispersible polyisocyanates containing alkoxysilane groups |
US6096823A (en) * | 1998-10-14 | 2000-08-01 | Bayer Corporation | Moisture-curable compounds containing isocyanate and alkoxysilane groups |
DE19849817A1 (de) * | 1998-10-29 | 2000-05-04 | Bayer Ag | Alkoxysilan-Endgruppen aufweisende Polyurethanprepolymere, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Herstellung von Dichtstoffen |
US6111010A (en) * | 1998-12-23 | 2000-08-29 | Bayer Corporation | Aqueous compounds containing alkoxysilane and/or silanol groups |
US6265517B1 (en) * | 1999-09-07 | 2001-07-24 | Bostik, Inc. | Silylated polyether sealant |
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HK1045852A1 (en) | 2002-12-13 |
EP1169370A1 (de) | 2002-01-09 |
HK1045852B (zh) | 2006-04-13 |
TR200102773T2 (tr) | 2003-01-21 |
KR100677788B1 (ko) | 2007-02-05 |
TW581775B (en) | 2004-04-01 |
CN1345345A (zh) | 2002-04-17 |
IL145213A0 (en) | 2002-06-30 |
CZ20013475A3 (cs) | 2002-01-16 |
PL351796A1 (en) | 2003-06-16 |
IL145213A (en) | 2006-08-20 |
HUP0200582A2 (en) | 2002-07-29 |
PT1169370E (pt) | 2006-07-31 |
BR0009480B1 (pt) | 2010-04-06 |
KR20010108408A (ko) | 2001-12-07 |
WO2000059974A1 (de) | 2000-10-12 |
CA2364598A1 (en) | 2000-10-12 |
AU4107300A (en) | 2000-10-23 |
ES2258450T3 (es) | 2006-09-01 |
BR0009480A (pt) | 2002-01-15 |
DE19914879A1 (de) | 2000-10-05 |
DE50012408D1 (de) | 2006-05-11 |
MXPA01009815A (es) | 2002-06-21 |
CZ301652B6 (cs) | 2010-05-12 |
EP1169370B1 (de) | 2006-03-15 |
ATE320457T1 (de) | 2006-04-15 |
CA2364598C (en) | 2009-11-17 |
US6762241B1 (en) | 2004-07-13 |
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