CN101257974A - 聚异氰脲酸酯硬质泡沫及其生产的方法 - Google Patents
聚异氰脲酸酯硬质泡沫及其生产的方法 Download PDFInfo
- Publication number
- CN101257974A CN101257974A CNA2006800322193A CN200680032219A CN101257974A CN 101257974 A CN101257974 A CN 101257974A CN A2006800322193 A CNA2006800322193 A CN A2006800322193A CN 200680032219 A CN200680032219 A CN 200680032219A CN 101257974 A CN101257974 A CN 101257974A
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- China
- Prior art keywords
- rigid foams
- catalyst
- blowing agent
- catalyst system
- polysiocyanurate rigid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000000034 method Methods 0.000 title claims abstract description 46
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
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- 229920000582 polyisocyanurate Polymers 0.000 title abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 48
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 56
- 239000012948 isocyanate Substances 0.000 claims description 38
- 150000002513 isocyanates Chemical class 0.000 claims description 37
- 239000004604 Blowing Agent Substances 0.000 claims description 34
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 28
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- 239000003063 flame retardant Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000003381 stabilizer Substances 0.000 claims description 11
- 238000005829 trimerization reaction Methods 0.000 claims description 10
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- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
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- 229940105325 3-dimethylaminopropylamine Drugs 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 3
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- GTACSIONMHMRPD-UHFFFAOYSA-N 2-[4-[2-(benzenesulfonamido)ethylsulfanyl]-2,6-difluorophenoxy]acetamide Chemical compound C1=C(F)C(OCC(=O)N)=C(F)C=C1SCCNS(=O)(=O)C1=CC=CC=C1 GTACSIONMHMRPD-UHFFFAOYSA-N 0.000 claims 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 24
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- 238000007373 indentation Methods 0.000 description 13
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- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
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- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
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- 239000000463 material Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
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- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 5
- 239000005642 Oleic acid Substances 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
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Abstract
本发明涉及一种特别是用于甲酸发泡的聚异氰脲酸酯硬质泡沫的催化剂体系以及生产该聚异氰脲酸酯硬质泡沫的方法和可由这种方法得到的聚异氰脲酸酯硬质泡沫。
Description
本发明涉及一种催化剂体系,其包含:
i)至少一种具有如下结构的化合物:
其中R1为CH3、CH2-CH2-N(CH3)2或CH2-CH2OH,和
R2为H、CH2-CH2OH或CH2-CH2N(CH3)2,以及
ii)至少一种三聚催化剂。
此外,本发明涉及该催化剂体系在生产借助甲酸发泡的聚异氰脲酸酯硬质泡沫中的用途和一种生产借助甲酸发泡且包含该催化剂体系的聚异氰脲酸酯硬质泡沫的方法。本发明的其它实施方案示于权利要求、说明书和实施例中。不言而喻的是上述特征和还将在下文主题中说明的特征在每种情况下不仅可以所示组合使用,且还可以不超出本发明范围的其它组合使用。
聚异氰脲酸酯泡沫,尤其是聚异氰脲酸酯硬质泡沫长期以来是已知的并且在文献中广泛描述。它们通常通过使多异氰酸酯与具有对异氰酸酯基团呈反应性的氢原子的化合物,通常是聚醚醇、聚酯醇或这两者反应而生产,其中异氰酸酯指数为180或更高。这导致不仅形成了通过使异氰酸酯与具有反应性氢原子的化合物反应而形成的脲烷结构,而且由于异氰酸酯基团相互间的反应还形成了通过使异氰酸酯基团与其它基团如聚氨酯基团反应而形成的异氰脲酸酯结构或其它结构。
通常而言,将发泡剂和胶凝催化剂,通常是胺和三聚催化剂用作生产聚异氰脲酸酯硬质泡沫的催化剂。在现有技术中还发现包含各种催化剂的混合物的催化剂体系。
这些聚异氰脲酸酯硬质泡沫通常使用物理和化学发泡剂生产。对本发明而言,化学发泡剂为通过与异氰酸酯反应形成气态产物的化合物。物理发泡剂为在用于聚氨酯生产的原料中溶解或乳化且在聚氨酯形成条件下蒸发的化合物。可行的化学发泡剂尤其为水以及羧酸。所用物理发泡剂例如为含氯氟烃、含氢氟烃、烃和液体CO2。
JP 2002338651描述了将水用作化学发泡剂和尤其包含具有3-20个碳原子的羧酸的盐和季铵盐的催化剂体系用于生产聚氨酯泡沫。在此给出的实施例中,将五甲基二亚乙基三胺(PMDETA)和二甲基环己胺(DMCHA)用作额外的催化剂。
羧酸、主要是甲酸在制备聚氨酯泡沫中作为化学发泡剂的用途同样是长期已知的。
US 5,143,945描述了使用三聚催化剂和发泡剂水和甲酸生产聚异氰脲酸酯泡沫。
美国专利5214076描述了在可包含甲酸的发泡剂和发泡催化剂如五甲基二亚乙基三胺存在下由芳族聚酯醇和芳族胺聚醚醇生产开孔碳化二亚胺-异氰脲酸酯泡沫。
另一方面,美国专利5478494和5770635描述了使用作为发泡剂的甲酸和延迟发泡剂如二(2-(N,N-二甲基氨基)乙基)醚(其例如被乙酸封端)以及包含脂环族或脂族叔胺的延迟胶凝催化剂生产聚异氰脲酸酯硬质泡沫的特定多元醇组合物,其中所述聚异氰脲酸酯硬质泡沫用于分批生产夹心元件。催化剂的作用通过用羧酸封端而延迟。
EP 1435366描述了酚醛聚醚醇在以分批和连续方法生产借助甲酸发泡的聚异氰脲酸酯和聚氨酯改性的聚异氰脲酸酯硬质泡沫中的用途。这里,可使用一种或多种催化剂,例如胺催化剂如五甲基二亚乙基三胺和锡催化剂如羧酸的锡盐。
异氰脲酸酯硬质泡沫优选通过连续方法如通过双带方法而生产。将水用作生产聚异氰脲酸酯硬质泡沫的化学发泡剂受到限制,因为显著量的异氰酸酯在与异氰酸酯反应产生发泡气体中消耗。
如果要实现异氰脲酸酯硬质泡沫的好的燃烧性能特征,则>300的异氰酸酯指数是必需的。此外,希望在100∶110-100∶230的多元醇∶异氰酸酯的常规混合比下操作,因为现有的机器技术和要确保异氰酸酯和多元醇组分的最佳混合。甚至在多元醇∶异氰酸酯的混合比=100∶230时,也不再可能在基于多元醇组分超过1重量份或更多的水下实现所需的>300的异氰酸酯指数。为此,通常仅将小比例水以及物理发泡剂,通常是烃如戊烷在现有技术中大量使用以获得所需量的发泡气体。这又对聚异氰脲酸酯硬质泡沫的阻燃性能具有负面效应。从环境角度来看且因为通常很高的价格,使用含氯氟烃和含氢氟烃通常不是好的替代物。
在由现有技术已知的方法中,作为发泡剂的甲酸具有用甲酸发泡的聚异氰脲酸酯硬质泡沫固化慢的缺点。在分批方法中,这导致模塑时间很长且因此导致经济性差,在连续方法中其导致带速很慢,从工程学的角度来看难以控制。
聚异氰脲酸酯硬质泡沫尤其用于绝热,例如制冷设备、容器或建筑物,在后者中主要用作绝热板或用于金属-异氰脲酸酯-金属夹心元件中。就建筑产品而言,European Commission已经根据EN 13823开发了标准燃烧试验“single burning item”试验(SBI试验),其不仅考虑了材料中火焰的传播,而且还考虑了烟的释放。此外,保险公司近来已经引入了在某些情况下明显超过法定要求的额外的燃烧试验。防损标准LPS 1181就是一个实例。
这类聚异氰脲酸酯硬质泡沫的常见问题还有优选在金属覆盖层的界面处形成表面缺陷。这些缺陷通常为在泡沫和金属片间夹杂了气体。尤其是在热作用下,这些泡沫表面缺陷导致形成不平的金属表面。这类表面缺陷例如可由包含在覆盖层后侧上的表面涂层中的添加剂,例如流动改进剂、脱气剂或疏水化剂造成。因为夹心元件主要用于建筑物的绝热,它们不仅具有提供绝热的目的,而且在显著程度上形成这些建筑物的外部。因此金属片中由于表面缺陷而造成的不平导致较低质量的产品。泡沫表面的改进减小了这类表面缺陷发生的频率并因此导致了这类金属-聚异氰脲酸酯-金属夹心元件的表面的视觉改进。
此外,表面缺陷同样可导致损害覆盖层与泡沫的粘合。例如当将这些元件用于建筑物外表面结构时,这同样有大问题。如果覆盖层的粘合由于表面缺陷而受到很大损害时,在极端情况下可发生金属片的完全脱离。
此外,希望改进聚异氰脲酸酯硬质泡沫相对于水发泡体系的固化,因为这样聚异氰脲酸酯硬质泡沫在较早时间内具有足够硬度并因此可更快速地从模具中取出。这将可使生产率增加,由此可更经济地操作装置。同样,该泡沫将可在连续法中以令人满意的带速生产。这里,生产率和装置的经济性也可通过较快的固化时间和因此可能较高的带速而改进,这使得甲酸可作为经济的连续生产夹心元件的发泡剂。
因此,本发明的目的为相比于现有技术改进聚异氰脲酸酯硬质泡沫的表面并同时降低表面缺陷的频率。同样,本发明的目的为提供借助甲酸发泡的聚异氰脲酸酯硬质泡沫体系,其显示了好的固化、弹性模量、压缩强度和低的脆度且在这些特征方面均可与已知的聚异氰脲酸酯硬质泡沫相当,从而可例如借助双带方法连续生产。
本发明的另一目的为提供一种相比于现有技术改进了SBT测试结果,尤其是测量值Figra、THR、Smogra和TSP的聚异氰脲酸酯硬质泡沫。
为此,本发明进一步提供了一种不使用卤代发泡剂而满足防火标准LPS 1181第一部分B级的硬质泡沫体系。
令人惊讶地发现将权利要求1所述的催化剂混合物用于生产聚异氰脲酸酯硬质泡沫改进了所生产硬质泡沫的泡沫表面,且聚异氰脲酸酯硬质泡沫夹心元件中表面缺陷的发生频率可以该方式降低。同时,固化和其它机械性能如压缩强度和弹性模量可维持在聚氨酯硬质泡沫水平,甚至有时还得以改进。同样可生产满足SBI测试要求,且与由现有技术已知的聚氨酯硬质泡沫相比,在SBI测试的测量值Figra、THR、Smogra和TSP方面显示了显著改进的聚异氰脲酸酯硬质泡沫。
对本发明而言,聚异氰脲酸酯为不仅包含氨基甲酸乙酯基团而且包含其它基团的聚合型异氰酸酯加合物。这些其它基团例如通过使异氰酸酯基团与其本身如异氰脲酸酯基团反应,或通过使异氰酸酯基团与除羟基之外的基团反应而形成,其中所述基团通常与氨基甲酸乙酯基团一起存在于聚合物中。对本发明而言,聚异氰脲酸酯的异氰酸酯指数为180或更高。
对本发明而言,异氰酸酯指数为异氰酸酯基团与对异氰酸酯呈反应性的基团的化学计量比乘以100。对本发明而言,对异氰酸酯呈反应性的基团为包含在反应混合物中且对异氰酸酯呈反应性的所有基团,其包括化学发泡剂,但不包括异氰酸酯基团本身。
对本发明而言,聚异氰脲酸酯硬质泡沫为发泡的聚异氰脲酸酯,优选根据DIN 7726的泡沫,即根据DIN 53 421/DIN EN ISO 604所述泡沫在10%的形变下具有大于或等于80kPa,优选大于或等于150kPa,特别优选大于或等于180kPa的压缩应力或压缩强度。此外,聚异氰脲酸酯硬质泡沫具有大于85%,优选大于90%的根据DIN ISO 4590的闭孔比例。
本发明聚异氰脲酸酯硬质泡沫优选通过如下方法生产,其中:
a)使异氰酸酯与如下物质反应:
b)具有对异氰酸酯呈反应性的基团的化合物,
c)包含甲酸的发泡剂,
d)催化剂体系,和合适的话,
e)泡沫稳定剂、阻燃剂和其它添加剂,
其中使用根据权利要求1的本发明催化剂体系。
关于所用组分a)至e),可提供如下细节。
a)作为异氰酸酯,可使用所有已知的有机二异氰酸酯和多异氰酸酯。具体而言,使用常用的脂族、脂环族,尤其是芳族二异氰酸酯和/或多异氰酸酯。优选使用甲苯二异氰酸酯(TDI)、二苯基甲烷二异氰酸酯(MDI),尤其是粗MDI,即二苯基甲烷二异氰酸酯和多亚苯基多亚甲基多异氰酸酯的混合物,其已知为聚合MDI。所述异氰酸酯也可被改性,例如通过掺入缩脲二酮(uretdione)、氨基甲酸酯、异氰脲酸酯、碳化二亚胺、脲基甲酸酯,尤其是脲烷基团而进行改性。
为生产聚异氰脲酸酯硬质泡沫,特别优选使用粗MDI。
此外,可将预聚物用作异氰酸酯组分。这些预聚物由上述异氰酸酯和下文所述聚醚或聚酯或这两者制备,且其NCO值为20-30,优选25-30。异氰脲酸酯结构可包含在这些预聚物中。
b)具有对异氰酸酯呈反应性的基团,即对异氰酸酯基团呈反应性的氢原子的可行化合物尤其为在分子中带有至少1.5个,例如1.5-5个,优选2-3个选自OH基团、SH基团、NH基团、NH2基团和酸性CH基团如β-二酮基,优选OH基团的反应性基团的化合物。这里,分子中反应性基团数目应认为是相当于具有对异氰酸酯基团呈反应性氢原子的分子数的平均值。
为生产优选通过本发明方法生产的聚异氰脲酸酯硬质泡沫,尤其是使用具有1.5-8个OH基团的化合物。优选使用聚醚醇、聚酯醇或这两者。这些聚醚醇和/或聚酯醇特别优选在分子中具有1.5-8个,尤其是2-4个OH基团。在生产聚异氰脲酸酯硬质泡沫中所用的聚醚醇和/或聚酯醇的羟基数优选为100-850mg KOH/g,特别优选100-400mg KOH/g,尤其是150-300mg KOH/g。分子量优选大于400g/mol。
聚醚多元醇可通过已知方法,例如使用碱金属氢氧化物如氢氧化钠或氢氧化钾或碱金属醇盐如甲醇钠、乙醇钠或乙醇钾或异丙醇钾作为催化剂,并加入至少一种以键合形式包含2-8个,优选2-4个反应性氢原子的起始分子通过阴离子聚合,或使用路易斯酸如五氯化锑、氟化硼醚化物或漂白土作为催化剂通过阳离子聚合而由一种或多种在亚烷基中具有2-4个碳原子的氧化烯制备。
合适的氧化烯例如为四氢呋喃、1,3-氧化丙烯,1,2-或2,3-氧化丁烯、氧化苯乙烯,优选氧化乙烯和1,2-氧化丙烯,特别优选氧化乙烯。氧化烯可单独,或者依次或者作为混合物使用。
可行的起始分子例如为乙二醇,二甘醇、甘油、三羟甲基丙烷、季戊四醇、蔗糖、山梨糖醇、甲胺、乙胺、异丙胺、丁胺、苄胺、苯胺、甲苯胺、甲苯二胺、萘胺、乙二胺、二亚乙基三胺、4,4′-亚甲基二苯胺、1,3-丙二胺、1,6-己二胺、乙醇胺、二乙醇胺、三乙醇胺以及其它二元或多元醇或单官能或多官能胺。优选使用乙二醇、二甘醇、甘油、三羟甲基丙烷和甲苯二胺。
所用聚酯醇通常通过具有2-12个碳原子的多官能醇与具有2-12个碳原子的多官能羧酸或其酸酐的缩合而制备,其中所述多官能醇例如为乙二醇、二甘醇、丁二醇、三羟甲基丙烷、甘油或季戊四醇,其中所述多官能羧酸例如为琥珀酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、癸烷二甲酸、马来酸、富马酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、聚对苯二甲酸乙二酯和萘二甲酸异构体的再生物(recyclate),优选邻苯二甲酸、间苯二甲酸、对苯二甲酸、聚对苯二甲酸乙二酯和萘二甲酸异构体的再生物。特别优选由邻苯二甲酸酐和/或对苯二甲酸和/或聚对苯二甲酸乙二酯的再生物制备的聚酯醇。
作为制备聚酯的其它原料,还可伴随使用疏水性物质。疏水性物质为包含非极性有机基团且具有至少一个选自羟基、羧酸、羧酸酯或其混合物的反应性基团的水不溶性物质。疏水性材料的当量为130-1000g/mol。例如可使用脂肪酸如硬脂酸、油酸、棕榈酸、月桂酸或亚油酸,以及脂和油如蓖麻油、玉米油、葵花油、大豆油、椰子油、橄榄油或妥尔油。如果聚酯包含疏水性物质,则疏水性物质的比例基于聚酯醇的全部单体含量优选为1-30摩尔%,特别优选4-15摩尔%。
所用聚酯醇优选具有1.5-5,特别优选1.5-4的官能度。
在优选实施方案中,具有对异氰酸酯基团呈反应性的氢原子的化合物包含至少一种聚酯。在特别优选的实施方案中,具有对异氰酸酯基团呈反应性的氢原子的化合物包含至少一种包含至少一种疏水性物质的聚酯。
还可使用增链剂和/或交联剂。所用增链剂和/或交联剂尤其为在每种情况下分子量小于400,优选为60-300的双官能或三官能胺和醇,尤其是二醇、三醇或这两者。
作为发泡剂组分c),使用包含甲酸的发泡剂。甲酸可作为单独的发泡剂或作为与水和/或物理发泡剂的混合物使用。作为物理发泡剂,优选使用烃、卤代烃如含氯氟烃(CFC)、含氢氯氟烃(HCFC)或含氟烃(HFC)和其它化合物,例如全氟代链烷烃如全氟己烷,以及醚、酯、酮和缩醛或其混合物。优选含氢氟烃如1,1,1,3,3-五氟丁烷(HFC 365mfc)、1,1,1,3,3-五氟丙烷(HFC 245fa)、1,1,1,2-四氟乙烷(HFC 134a)或1,1,1,2,3,3,3-七氟丙烷(HFC227ea)及其混合物。此外,有利的是还可将诸如戊烷异构体和衍生物的烃用作物理发泡剂。
优选使用甲酸与含氢氟烃(HFC)和/或烃的组合。在优选实施方案中,发泡剂组分c)除了甲酸中的不超过1.5重量%水含量外不包含水。组分b)至e)的总水含量在每种情况下基于组分b)至e)优选小于0.5重量%,特别优选小于0.3重量%。在另一优选实施方案中,甲酸与烃,尤其是与正戊烷或戊烷异构体组合使用。
发泡剂组分c)的用量基于组分b)至e)的总重量通常为1-30重量%,优选2-20重量%,特别优选2-10重量%。
在发泡剂组分c)中甲酸的摩尔浓度优选大于10摩尔%,优选大于20摩尔%,特别优选大于35摩尔%。
还优选发泡剂组分c)基于组分b)至e)的总重量包含小于5重量%,更优选小于2重量%,特别优选小于1重量%,尤其是0重量%的含氯氟烃和/或氯代烃。
生产本发明聚异氰脲酸酯硬质泡沫的催化剂体系d)包含如下物质:
i)具有如下结构的化合物:
ii)三聚催化剂,和合适的话,
iii)另一催化剂组分,
其中另一催化剂组分iii)为具有最多6个氮原子且不同于催化剂组分i)和ii)的胺化合物。
关于本发明催化剂体系的组分i)、ii)和iii),可描述如下。
在化合物i)中,R1=CH3、CH2CH2N(CH3)2或CH2CH2OH且R2=H、CH2CH2OH或CH2CH2N(CH3)2。尤其是,该催化剂组分i)为二(二甲基氨基乙基)醚、N,N,N-三甲基氨基乙基乙醇胺、N,N-二甲基氨基乙基N-甲基-N-羟基乙基氨基乙基醚、N,N-二甲基氨基乙氧基乙醇或二甲基乙醇胺。
化合物ii)催化NCO基团相互间的三聚反应。可作为实例提及金属盐,尤其是羧酸的铵盐、碱金属或碱土金属盐。优选使用下述酸的盐:具有1-20个碳原子的线性或支化,取代或未取代,饱和或不饱和的脂族羧酸或芳族羧酸,例如甲酸、乙酸、辛酸、酒石酸、柠檬酸、油酸、硬脂酸和蓖麻油酸,或具有6-20个碳原子的取代或未取代的芳族羧酸,例如苯甲酸和水杨酸。特别优选甲酸钾、乙酸钾、辛酸钾、甲酸铵、乙酸铵和辛酸铵,尤其是甲酸钾。
此外,化合物ii)可包含同样催化NCO基团相互间的三聚反应的含胺催化剂。这些例如包括1,3,5-三(3-二甲基氨基丙基)六氢-s-三嗪、三-3-二甲基氨基丙胺、五甲基二亚丙基三胺和2,4,6-三(二甲基氨基乙基)苯酚。
化合物(iii)包含1、2、3、4、5或6个氮原子和小于5个氧原子。特别优选使用N-甲基二乙醇胺、六甲基三亚乙基四胺、五甲基二亚乙基三胺、二(二甲基氨基乙基)醚、N,N,N-三甲基氨基乙基乙醇胺、N,N-二甲基氨基乙基N-甲基-N-羟基乙基氨基乙基醚、N,N-二甲基氨基乙氧基乙醇、N,N-二(3-二甲基氨基丙基)氨基-2-丙醇胺、四甲基六亚甲基二胺、三-3-二甲基氨基丙胺、二甲基乙醇胺、三乙胺、二甲基环己胺、五甲基二亚丙基三胺、N-甲基咪唑、1,3,5-三(3-二甲基氨基丙基)六氢-s-三嗪、2,4,6-三(二甲基氨基乙基)苯酚、N-二甲基氨基丙基脲或双(N-二甲基氨基丙基)脲。尤其是使用二(二甲基氨基乙基)醚、N,N,N-三甲基氨基乙基乙醇胺、N,N-二甲基氨基乙氧基乙醇或二甲基乙醇胺。
优选使用其中二(二甲基氨基乙基)醚、N,N,N-三甲基氨基乙基乙醇胺或N,N-二甲基氨基乙氧基乙醇作为组分i)存在,甲酸钾作为组分ii)存在的混合物。在另一具体实施方案中,混合物进一步包含由N,N,N-三甲基氨基乙基乙醇胺、N,N-二甲基氨基乙氧基乙醇或二甲基乙醇胺组成的组分iii)。在另一具体实施方案中,催化剂混合物由i)二(二甲基氨基乙基)醚、ii)甲酸钾和iii)N,N,N-三甲基氨基乙基乙醇胺组成。
在包含i)、ii)和合适的话iii)的整个催化剂混合物中催化剂ii)的摩尔分数为30-90摩尔%,优选40-90摩尔%,特别优选45-85摩尔%。这里,将甲酸钾用作催化剂ii)。
组分e)包含通常可额外用于生产聚异氰脲酸酯的化合物。这些化合物包括泡沫稳定剂、阻燃剂和其它添加剂,例如其它催化剂和抗氧化剂。
泡沫稳定剂为在泡沫形成过程中促进形成规整泡孔结构的物质。
可提及的实例为:含聚硅氧烷的泡沫稳定剂如硅氧烷-氧化烯共聚物和其它有机聚硅氧烷。还有脂肪醇、羰基合成醇、脂肪胺、烷基苯酚、二烷基苯酚、烷基甲酚、烷基间苯二酚、萘酚、烷基萘酚、萘胺、苯胺、烷基苯胺、甲苯胺、双酚A、烷基化双酚A、聚乙烯醇的烷氧基化产物以及甲醛和烷基苯酚、甲醛和二烷基苯酚、甲醛和烷基甲酚、甲醛和烷基间苯二酚、甲醛和苯胺、甲醛和甲苯胺、甲醛和萘酚、甲醛和烷基萘酚以及甲醛和双酚A的缩合产物的烷氧基化产物,以及两种或更多种这些泡沫稳定剂的混合物。
泡沫稳定剂的用量基于组分b)-e)的总重量优选为0.5-4重量%,特别优选1-3重量%。
作为烷氧基化试剂,例如可使用氧化乙烯、氧化丙烯、聚THF和高级同系物。
可使用的阻燃剂通常为由现有技术已知的阻燃剂。合适的阻燃剂例如为溴化醚(Ixol B 251)、溴化醇如二溴新戊醇、三溴新戊醇和PHT-4-二醇,以及氯化磷酸酯如磷酸三(2-氯乙基)酯、磷酸三(2-氯异丙基)酯(TCPP)、磷酸三(1,3-二氯异丙基)酯、磷酸三(2,3-二溴丙基)酯和四(2-氯乙基)亚乙基二磷酸酯,或其混合物。
除了上述卤代磷酸酯之外,还可使用无机阻燃剂如红磷、包含红磷的制剂、可膨胀石墨、氧化铝水合物、三氧化二锑、氧化砷、多磷酸铵和硫酸钙或三聚氰酸衍生物如三聚氰胺或至少两种阻燃剂如多磷酸铵和三聚氰胺的混合物以及合适的话淀粉使根据本发明生产的聚异氰脲酸酯硬质泡沫阻燃。
作为其它不含卤素的液体阻燃剂,可使用乙烷膦酸二乙酯(DEEP)、磷酸三乙酯(TEP)、二甲基丙基膦酸酯(DMPP)、二苯基甲苯基磷酸酯(DPC)和其它。
优选使用磷酸三(2-氯异丙基)酯(TCPP)、乙烷膦酸二乙酯(DEEP)、二苯基甲苯基磷酸酯(DPC)或可膨胀石墨。在特别优选的实施方案中,仅使用不含卤素的阻燃剂。
对本发明而言,阻燃剂的用量基于组分b)-e)的总重量优选为0-60重量%,特别优选5-50重量%,更优选10-30重量%,尤其是5-40重量%。
此外,可使用常规填料。
为生产聚异氰脲酸酯硬质泡沫,使多异氰酸酯a)和组分b)-e)以使得异氰酸酯指数为180-700,优选250-500,尤其是300-400的量反应。
聚异氰脲酸酯硬质泡沫可借助已知方法(例如双带)分批或连续生产。本文所述的发明涉及这两种方法,但优选连续双带方法。在该方法中,将上部覆盖层和底部覆盖层,例如金属层、铝箔或纸在辊上辗轧和合适的话切削(profiled)、加热并电晕处理以改进将泡沫施加至覆盖层上的能力。然后使包含组分a)-d)和合适的话e)的反应混合物例如在高压混合头中混合,施加至底部覆盖层并在已知为双带的上部和底部覆盖层间固化。随后将元件切割至所需长度。合适的话,在施加聚异氰脲酸酯硬质泡沫体系之前,将底漆额外施加至底部覆盖层。
已经发现,特别有利的是使用两组分方法。为此,具有至少两个对异氰酸酯呈反应性的基团的化合物、化学发泡剂、催化剂和合适的话泡沫稳定剂、阻燃剂和其它添加剂形成多元醇组分,同时用于反应的异氰酸酯形成异氰酸酯组分。物理发泡剂既可包含在多元醇组分中,也可包含在异氰酸酯组分中。在聚异氰脲酸酯硬质泡沫的实际生产中,接着使多元醇组分和异氰酸酯组分相互反应。
在生产聚异氰脲酸酯硬质泡沫过程中或在开始生产聚异氰脲酸酯硬质泡沫之前可将发泡剂组分c),尤其是甲酸加入多元醇组分中。例如,可通过低压技术将发泡剂组分c),尤其是甲酸在聚异氰脲酸酯硬质泡沫的生产方法中分开计量加入多元醇组分中,或通过高压技术在混合头处直接加入。
本发明催化剂体系的特别优点为当将本发明催化剂体系用于生产聚异氰脲酸酯硬质泡沫时得到特别少的表面缺陷。表面缺陷的频率通过光学方法测量。在该方法中,例如将平行于下部覆盖层的平面距离底部覆盖层数毫米放置在泡沫样品中,并分离出其上的材料,其中底部覆盖层即为已在双带方法中将聚氨酯反应混合物施加至其上的覆盖层。以5°的开度角照明以该方式获得的泡沫表面,并将表面缺陷的投影面积除以横截面的总面积。阴影覆盖面积的比例基于总面积优选小于15%,更优选小于10%,尤其是小于5%。
本发明的聚异氰脲酸酯硬质泡沫具有好的压缩强度和低脆度。根据DIN 53421垂直于发泡方向测量的压缩强度优选大于0.08N/mm2,特别优选大于0.12N/mm2,尤其是大于0.15N/mm2。
此外,本发明聚异氰脲酸酯硬质泡沫具有低的针高度(needle height)。对在聚苯乙烯杯中由80g混合物生产的泡沫测定针高度。其显示了泡沫在纤维时间(fiber time)和完全固化之间持续上升的高度。达到纤维时间之后泡沫进一步过度膨胀是不希望的,因为其对泡沫的机械性能如弹性模量和压缩强度具有不利影响。本发明聚异氰脲酸酯硬质泡沫的针高度优选为小于40mm,特别优选小于35mm,尤其是小于30mm。
此外,本发明聚异氰脲酸酯硬质泡沫为用于制冷设备、容器和建筑物中的良好绝热材料。因此,本发明包括包含本发明聚异氰脲酸酯硬质泡沫作为绝热材料的制冷设备、容器和建筑物。
本发明的其它优点为借助本发明催化剂体系实现聚异氰脲酸酯硬质泡沫的非常好的固化。固化可借助压痕测试测定。在该测试中,在聚苯乙烯杯中混合组分之后的3、4、5、6、8和10分钟,将具有半径为10mm的半球端的钢硬度试验压头压进借助拉伸/压缩测试机器形成的泡沫中10mm深度。为此所需的最大力(N)为泡沫固化的量度。在3分钟之后,优选其大于60牛顿,特别优选大于65牛顿,尤其是大于70牛顿,在10分钟后优选大于130牛顿,特别优选大于140牛顿,尤其是大于150牛顿。在3、4、5、6、8和10分钟后用于测试的力总计优选大于500牛顿,特别优选大于550牛顿,尤其是大于600牛顿。因此,本发明的聚异氰脲酸酯硬质泡沫很适合于进行生产金属-聚异氰脲酸酯硬质泡沫-金属夹心元件的双带方法。
此外,聚异氰脲酸酯硬质泡沫具有特别低的热传导,这使其成为例如在建筑领域中优异的绝热材料。热传导根据DIN 52612测量且在生产聚异氰脲酸酯硬质泡沫之后直接测量,其小于30mW/mK,优选小于28mW/mK,特别优选小于26mW/mK。
例如在SBI测试中测量,本发明硬质泡沫还具有特别好的燃烧性能。当在该测试中使用80mm厚的具有50μm厚度的铝覆盖层的绝热板时,优选得到如下测量值:Figra<250W/s,特别优选<200W/s,THR<5.5MJ,特别优选<5.2MJ,Smogra<100m2/s2,特别优选<90m2/s2,以及TSP<110m2,特别优选<100m2。
本发明通过如下实施例说明:
测量方法:
固化:
固化借助压痕测试测定。为此,在聚苯乙烯杯中混合组分之后的3、4、5、6、8和10分钟,将具有半径为10mm的半球端的钢硬度试验压头压进借助拉伸/压缩测试机器形成的泡沫中10mm深度。为此所需的最大力(N)为泡沫固化的量度。作为聚异氰脲酸酯硬质泡沫脆度的量度,在压痕试验中测定在硬质泡沫表面具有可见的断裂区的时间点。
表面缺陷
评价表面缺陷频率的试验样品通过双带方法生产。
表面缺陷通过上述方法测定。为此,如上所述预热20cm×30cm泡沫样品并照明,随后拍照。随后将泡沫照片二元化(binarized)并重叠。二元化照片的黑色区域的积分面积除以照片的总面积并因此为表面缺陷频率的测量值。
此外,对聚异氰脲酸酯硬质泡沫表面性质进行额外定性评价,其中从1m×2m泡沫样品中除去覆盖层并视觉评价表面的表面缺陷。
压缩强度
根据DIN 53421/DIN EN ISO 604垂直于通过双带方法生产的夹心元件上的覆盖层在40g/l的整体泡沫密度下测量聚异氰脲酸酯硬质泡沫的压缩强度和弹性压缩模量。
针高度
对在聚苯乙烯杯中使用80g混合物生产的直径为10.4cm的泡沫测定针高度。其显示了泡沫在纤维时间和实现完全固化之间持续上升的高度。纤维时间之后泡沫进一步过度膨胀是不希望的。
阻燃性
火焰高度根据EN ISO 11925-2测量。
SBI测试根据EN 13823进行。这里,使用具有铝覆盖层的夹心元件,其通过双带方法生产且泡沫厚度为80mm,每个铝覆盖层厚度为50μm。在SBI测试中,测量在借助标准化燃烧器施加火焰时的热释放[W/s]。所测参数为火焰增长速率(Figra)、总的放热(THR)、烟增长速率(Smogra)和总的烟产量(TSP)。Figra为最大能量释放和达到该最大值的时间的商。THR为开始施加火焰之后最初10分钟内的总的能量释放。Smogra为烟释放的最大值与达到该最大值的时间的商。TSP为开始施加火焰之后最初10分钟内的总的烟释放。
将the Test Loss Prevention Standard LPS 1181第1部分B级的表现规定在由the Loss Prevention Certification Board(LPCB)在2005年9月16日出版的对应标准中。在该试验中,车库由夹心元件建成并受到苛刻的火焰情况。火焰传播为判断测试表现的决定性准则。
生产聚异氰脲酸酯硬质泡沫
将异氰酸酯和对异氰酸酯呈反应性的组分与发泡剂、催化剂和所有其它添加剂在350的指数下一起发泡。在每种情况下设定45秒的恒定纤维时间和45g/l的整体泡沫密度。在通过双带方法生产的夹心元件的情况下,泡沫密度为40g/l。
本发明实施例:
实施例1:
多元醇组分
58重量份由邻苯二甲酸酐、二甘醇和油酸的酯化产物组成的聚酯醇,其羟基官能度为1.8,羟基数为200mg KOH/g
10重量份由乙二醇和氧化乙烯的醚组成的聚醚醇,其羟基官能度为2,羟基数为200mg KOH/g
30重量份阻燃剂磷酸三氯代异丙基酯(TCPP)
2重量份稳定剂;Tegostab B 8443(包含聚硅氧烷的稳定剂)
6重量份正戊烷
2.1重量份甲酸(99%)
1.5重量份甲酸钾(在乙二醇中,36重量%)
1.4重量份N,N,N-三甲基氨基乙基乙醇胺(Dabco T)
异氰酸酯组分
190重量份Lupranat M50(聚合MDI)
如上所述,将组分A和B相互发泡。压痕试验的结果、脆度、压缩强度、弹性压缩模量、针高度、SBI测试和表面性质的定性评价报道在表1中。
实施例2:
重复实施例1的程序,使用1.4重量份二(2-二甲基氨基乙基)醚(NiaxA1;70%,在二丙二醇中)代替1.4重量份N,N,N-三甲基氨基乙基乙醇胺(Dabco T)。压痕试验的结果、脆度和针高度报道在表2中。
实施例3:
重复实施例1的程序,使用0.6重量份N,N,N-三甲基氨基乙基乙醇胺(Dabco T)和0.6重量份二(2-二甲基氨基乙基)醚(Niax A1;70%,在二丙二醇中)代替1.4重量份N,N,N-三甲基氨基乙基乙醇胺(Dabco T)。压痕试验的结果、脆度和针高度报道在表2中。
实施例4:
重复实施例1的程序,使用0.6重量份N,N,N-三甲基氨基乙基乙醇胺(Dabco T)和0.6重量份二甲基乙醇胺(Lupragen N 101)代替1.4重量份N,N,N-三甲基氨基乙基乙醇胺(Dabco T)。压痕试验的结果、脆度和针高度报道在表2中。
实施例5:
重复实施例1的程序,区别在于用58重量份基于对苯二甲酸、二甘醇、三羟甲基丙烷和油酸的官能度为2.2,OH数为230的聚酯醇代替58重量份基于邻苯二甲酸酐的聚酯醇。压痕试验的结果、脆度、压缩强度、弹性压缩模量、针高度、SBI测试和表面性质的定性评价报道在表1中。该反应混合物也用于生产具有整合连接的夹心元件。这些夹心元件的厚度为120nm,且每一侧面对厚度为0.6mm的钢片。泡沫密度为45g/L。使这类壁元件经受防损标准LPS 1181第1部分B级测试;结果报道在表1中。
对比例1:
多元醇组分
58重量份由邻苯二甲酸酐、二甘醇和油酸的酯化产物组成的聚酯醇,其羟基官能度为1.8,羟基数为200mg KOH/g
10重量份由乙二醇和氧化乙烯的醚组成的聚醚醇,其羟基官能度为2,羟基数为200mg KOH/g
30重量份阻燃剂磷酸三氯代异丙基酯(TCPP)
2重量份稳定剂;Tegostab B 8443(包含聚硅氧烷的稳定剂)
13重量份正戊烷
0.8重量份水/二丙二醇混合物(60∶40)
1.5重量份甲酸钾(在乙二醇中,36重量%)
1.4重量份二(2-二甲基氨基乙基)醚(Niax A1;70重量%,在二丙二醇中)
异氰酸酯组分
190重量份Lupranat M50
如上所述,使组分A和B相互发泡。压痕试验的结果、脆度、压缩强度、弹性压缩模量、针高度、SBI测试和表面性质的定性评价报道在表1中。该反应混合物也用于生产具有整合连接的夹心元件。这些夹心元件的厚度为120nm,且每一侧面对厚度为0.6mm的钢片。泡沫密度为45g/L。使这类壁元件经受防损标准LPS 1181第1部分B级测试;结果报道在表1中。
对比例2:
重复对比例1的程序,使用6重量份正戊烷和2.1重量份99重量%浓度的甲酸作为发泡剂,代替13重量份正戊烷。此外,使用1.6重量份二甲基环己胺代替1.4重量份二(2-二甲基氨基乙基)醚(Niax A1;70重量%,在二丙二醇中)。压痕试验的结果、脆度和针高度报道在表2中。
对比例3:
重复对比例1的程序,使用6重量份正戊烷和2.1重量份99重量%浓度的甲酸作为发泡剂,代替13重量份正戊烷。此外,使用1.6重量份三乙胺代替1.4重量份二(2-二甲基氨基乙基)醚(Niax A1;70重量%,在二丙二醇中)。压痕试验的结果、脆度和针高度报道在表2中。
表1:
实施例1 | 实施例5 | 对比例1 | |
3分钟后的压痕试验[N] | 70 | 70 | 72 |
10分钟后的压痕试验[N] | 145 | 140 | 130 |
脆度:x分钟后表面断裂 | - | - | 6 |
弹性压缩模量[N/mm2] | 4.25 | 4.1 | 3.85 |
压缩强度[N/mm2] | 0.15 | 0.16 | 0.15 |
针高度[mm] | 29 | 31 | 35 |
根据EN ISO 11925-2的火焰高度[cm] | 6 | 5 | 11 |
根据EN 13823的Figra[W/s] | 222 | 210 | 267 |
根据EN 13823的THR[MJ] | 5.3 | 5.1 | 5.7 |
根据EN 13823的Smogra[m2/s2] | 83 | 86 | 105 |
根据EN 13823的TSP[m2] | 101 | 110 | 114 |
基底缺陷[%]/视觉评价 | 3.8/好 | 4.2/好 | 16.8/好 |
LPS 1181,第1部分,B级 | - | 合格 | 不合格 |
表1显示使用本发明催化剂体系生产聚异氰脲酸酯硬质泡沫使固化加速,脆度减小,弹性增加,改进了根据EN 13823的燃烧性能并使在恒定压缩强度下表面缺陷的频率降低。
表2:
实施例1 | 实施例2 | 实施例3 | 实施例4 | 对比例2 | 对比例3 | |
3分钟后的压痕试验[N] | 70 | 68 | 65 | 74 | 61 | 52 |
10分钟后的压痕试验[N] | 145 | 159 | 158 | 152 | 135 | 126 |
脆度:x分钟后表面断裂 | - | - | - | - | 6 | 6 |
针高度[mm] | 29 | 30 | 32 | 31 | 33 | 35 |
表2显示通过本发明方法生产的聚异氰脲酸酯硬质泡沫显示了改进的固化性能、较低的脆度和减小的针高度。
Claims (17)
1.一种催化剂体系,其包含:
i)至少一种具有如下结构的化合物:
其中R1为CH3、CH2-CH2-N(CH3)2或CH2-CH2OH,和
R2为H、CH2-CH2OH或CH2-CH2N(CH3)2,以及
ii)至少一种三聚催化剂。
2.根据权利要求1的催化剂体系,其中所述三聚催化剂ii)为羧酸的碱金属盐或碱土金属盐、1,3,5-三(3-二甲基氨基丙基)六氢-s-三嗪、三-3-二甲基氨基丙胺、五甲基二亚丙基三胺和/或2,4,6-三(二甲基氨基乙基)苯酚。
3.根据权利要求2的催化剂体系,其中所述三聚催化剂ii)选自甲酸钾、乙酸钾、辛酸钾、甲酸铵、乙酸铵、辛酸铵及其混合物。
4.根据权利要求3的催化剂体系,其中所述三聚催化剂ii)为甲酸钾。
5.根据权利要求1-4中任一项的催化剂体系,其中所述催化剂体系包含另一催化剂组分iii),其为具有最多6个氮原子且不同于催化剂组分i)和ii)的胺化合物。
6.一种生产聚异氰脲酸酯硬质泡沫的方法,其中:
a)使异氰酸酯与如下物质反应:
b)具有对异氰酸酯呈反应性的基团的化合物,
c)包含甲酸的发泡剂,
d)催化剂体系,和
e)可行的泡沫稳定剂、阻燃剂和其它添加剂,
其中所述催化剂体系为根据权利要求1-5中任一项的催化剂体系。
7.根据权利要求6的方法,其中连续生产所述聚异氰脲酸酯硬质泡沫。
8.根据权利要求7的方法,其中所述聚异氰脲酸酯硬质泡沫通过双带方法生产。
9.根据权利要求6-8中任一项的方法,其中所述发泡剂组分c)包含超过20摩尔%,优选超过35摩尔%的甲酸。
10.根据权利要求6-9中任一项的方法,其中所述发泡剂组分c)包含甲酸和物理发泡剂。
11.根据权利要求10的方法,其中所述物理发泡剂仅由含氢氟烃组成。
12.根据权利要求10的方法,其中所述物理发泡剂仅由烃,优选戊烷的衍生物组成。
13.根据权利要求6-12中任一项的方法,其中组分b)-e)包含小于0.5重量%,优选小于0.3重量%的水。
14.根据权利要求6-13中任一项的方法,其中对异氰酸酯呈反应性的化合物包含至少一种其单体组分包含1-20摩尔%疏水性物质的聚酯多元醇。
15.根据权利要求6-14中任一项的方法,其中为生产所述聚异氰脲酸酯硬质泡沫,使多异氰酸酯组分a)和组分b)-e)以使得异氰酸酯指数为180-700的量反应。
16.根据权利要求1-5中任一项的催化剂体系在生产借助甲酸发泡的聚异氰脲酸酯硬质泡沫中的用途。
17.一种可通过根据权利要求6-15中任一项的方法获得的聚异氰脲酸酯硬质泡沫。
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-
2005
- 2005-09-01 DE DE102005041763A patent/DE102005041763A1/de not_active Withdrawn
-
2006
- 2006-08-21 AT AT06792917T patent/ATE455596T1/de active
- 2006-08-21 KR KR1020087006816A patent/KR20080045228A/ko not_active Application Discontinuation
- 2006-08-21 WO PCT/EP2006/065487 patent/WO2007025888A1/de active Application Filing
- 2006-08-21 SI SI200630587T patent/SI1924356T1/sl unknown
- 2006-08-21 PL PL06792917T patent/PL1924356T3/pl unknown
- 2006-08-21 DE DE502006005991T patent/DE502006005991D1/de active Active
- 2006-08-21 US US12/065,359 patent/US20080234402A1/en not_active Abandoned
- 2006-08-21 JP JP2008528466A patent/JP2009507095A/ja active Pending
- 2006-08-21 ES ES06792917T patent/ES2338703T3/es active Active
- 2006-08-21 EP EP06792917A patent/EP1924356B1/de active Active
- 2006-08-21 PT PT06792917T patent/PT1924356E/pt unknown
- 2006-08-21 CN CN2006800322193A patent/CN101257974B/zh active Active
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CN104507993A (zh) * | 2012-05-30 | 2015-04-08 | 巴斯夫欧洲公司 | 制备聚氨酯硬质泡沫的方法 |
CN104507993B (zh) * | 2012-05-30 | 2016-09-21 | 巴斯夫欧洲公司 | 制备聚氨酯硬质泡沫的方法 |
CN104507991A (zh) * | 2012-07-27 | 2015-04-08 | 巴斯夫欧洲公司 | 含有磷化合物的聚氨酯泡沫 |
WO2016107388A1 (zh) * | 2014-12-31 | 2016-07-07 | 江苏奥斯佳材料科技有限公司 | 一种聚氨酯催化剂及其应用 |
US10889681B2 (en) | 2014-12-31 | 2021-01-12 | Jiangsu Osic Performance Materials Co. Ltd. | Polyurethane catalyst and application thereof |
CN107250229A (zh) * | 2015-02-20 | 2017-10-13 | 巴斯夫欧洲公司 | 具有高阻燃性的基于异氰酸酯的耐温泡沫 |
CN107250229B (zh) * | 2015-02-20 | 2021-04-06 | 巴斯夫欧洲公司 | 具有高阻燃性的基于异氰酸酯的耐温泡沫 |
CN109153764A (zh) * | 2016-05-18 | 2019-01-04 | 巴斯夫欧洲公司 | 制备聚异氰脲酸酯硬质泡沫的方法 |
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CN112204064A (zh) * | 2018-04-13 | 2021-01-08 | 科思创知识产权两合公司 | 用于生产异氰脲酸酯聚合物的胺催化剂的加合物 |
CN112204064B (zh) * | 2018-04-13 | 2023-07-28 | 科思创知识产权两合公司 | 用于生产异氰脲酸酯聚合物的胺催化剂的加合物 |
Also Published As
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---|---|
KR20080045228A (ko) | 2008-05-22 |
CN101257974B (zh) | 2010-11-10 |
ATE455596T1 (de) | 2010-02-15 |
EP1924356B1 (de) | 2010-01-20 |
DE502006005991D1 (de) | 2010-03-11 |
US20080234402A1 (en) | 2008-09-25 |
DE102005041763A1 (de) | 2007-03-08 |
EP1924356A1 (de) | 2008-05-28 |
PT1924356E (pt) | 2010-02-03 |
ES2338703T3 (es) | 2010-05-11 |
JP2009507095A (ja) | 2009-02-19 |
SI1924356T1 (sl) | 2010-04-30 |
PL1924356T3 (pl) | 2010-06-30 |
WO2007025888A1 (de) | 2007-03-08 |
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