CN103384689B - 基于芳族二羧酸的聚酯多元醇以及由其制备的硬质聚氨酯泡沫 - Google Patents
基于芳族二羧酸的聚酯多元醇以及由其制备的硬质聚氨酯泡沫 Download PDFInfo
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- CN103384689B CN103384689B CN201280010084.6A CN201280010084A CN103384689B CN 103384689 B CN103384689 B CN 103384689B CN 201280010084 A CN201280010084 A CN 201280010084A CN 103384689 B CN103384689 B CN 103384689B
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Abstract
本发明涉及基于芳族二羧酸或其衍生物的聚酯多元醇、以及涉及本发明的聚酯多元醇用于制备聚氨酯的用途。
Description
本发明涉及基于芳族二羧酸的聚酯多元醇及其用于制备硬质聚氨酯泡沫的用途。
通过有机的或改性有机的二异氰酸酯或多异氰酸酯与含有至少两个活泼氢原子的较高分子量的化合物——特别是与由环氧烷烃聚合得到的聚醚多元醇或由醇与二羧酸缩聚得到的聚酯多元醇——在聚氨酯催化剂、增链剂和/或交联剂、发泡剂以及其他助剂和添加剂的存在下反应来制备硬质聚氨酯泡沫是已知的并且记载于许多专利和文献出版物中。
可提及例如由R.Vieweg博士和A.博士所编的Kunststoffhandbuch,第VII卷,Polyurethane,Carl-Hanser-Verlag,Munich,第1版1966以及由G.Oertel博士所编的第2版1983和第3版1993。适当地选择形成组分及其比例使得能够制备具有极好机械性能的聚氨酯泡沫。
在本公开文本的上下文中,同义地使用术语“聚酯多元醇”(“polyester polyol”)、“聚酯多元醇”(“polyesterol”)、“聚酯醇”(“polyester alcohol”)和缩写“PESOL”。缩写“PEOL”意指聚醚多元醇(polyetherol),其等同于聚醚醇(polyether alcohol)。“多元醇”指的是含有至少两个游离OH基团的化合物。
当使用聚酯多元醇时,通常使用芳族二羧酸和/或脂族二羧酸与链烷二醇和/或链烷三醇或醚二醇的缩聚物。然而,也可加工聚酯废料,特别是聚对苯二甲酸乙二醇酯(PET)或聚对苯二甲酸丁二醇酯(PBT)废料。用于此目的的整个系列的方法是已知的并且已有记载。一些方法基于聚酯向对苯二甲酸二酯(例如对苯二甲酸二甲酯)的转化。DE-A1003714和US-A 5,051,528记载了这种利用甲醇和酯交换催化剂的酯交换反应。
US 3,138,562涉及“多孔聚氨酯塑料(Cellular PolyurethanePlastics)”,其公开了一种制备聚酯多元醇的方法,其中使用了三官能的醇(TMP)。其并未记载如何制备原料,例如聚醚醇(丙氧基化甘油)。
还已知基于对苯二甲酸的酯在燃烧性能方面优于基于邻苯二甲酸的酯。这一点例如在WO 2010/043624中示出。
聚醚多元醇还可用于制备聚氨酯以及作为形成聚酯多元醇的组分。
通常,这些聚醚多元醇通过OH官能的起始物的催化烷氧基化来制备。
所用的烷氧基化催化剂为常规的碱性化合物,特别是KOH。在一些情况下也可使用双金属氰化物(DMC)催化剂或卡宾(carbene)。
但是,就通常用于OH官能的化合物的烷氧基化作用的KOH催化剂而言,该反应需要随后进行后处理步骤以从产物中分离出催化剂。所述后处理通常通过中和以及随后的过滤来进行。但是,在待分离的催化剂中通常残留少量产物,这降低了产物收率。
能够无需进行聚醚多元醇的后处理将是合乎需要的(特别是由于多元醇的损耗以及该部分设备所需的投入)。但是,对常规利用的KOH催化作用而言,碱性催化剂将残留在聚醚多元醇中并且可妨碍随后用于制备聚酯多元醇的酸催化的酯化反应。
当用胺催化剂代替KOH时,可避免额外耗时的后处理的处理步骤。这些胺催化剂通常可留在产物中。
但是,如果聚醚多元醇产物与例如二羧酸将通过酯化反应进一步反应获得聚酯多元醇,则留在聚醚多元醇中的胺催化剂也可引发问题,这是因为其妨碍了通常由Lewis酸催化的酯化反应。
此外,已知胺化合物通常降低聚酯多元醇的水解稳定性。
因此,本发明的一个目的是提供一种聚酯多元醇,其特别由聚醚多元醇构建并且可以极少的费用(即,特别以极少的后处理和纯化步骤)制备,此外其还可毫无疑问地用于聚氨酯(PU)制备并生产优良的PU。
出人意料地,上述目的能够通过使用一种聚醚多元醇组分实现,所述聚醚多元醇组分可通过官能度大于或等于2的多元醇——特别是聚醚多元醇——与至少一个环氧烷烃在所述聚酯多元醇中的胺催化剂的存在下反应来制备。
因此,本发明提供一种聚酯多元醇,其包含以下化合物的酯化产物
a.10mol%至70mol%的二羧酸组合物,其含有
a1)50mol%至100mol%含量的芳族二羧酸或芳族二羧酸的混合物,基于二羧酸组合物a)计,
a2)0mol%至50mol%含量的一种或多种脂族二羧酸,基于二羧酸组合物a)计,
b.2mol%至30mol%的一种或多种脂肪酸和/或脂肪酸衍生物,
c.10mol%至70mol%的一种或多种含有2至18个碳原子的脂族二醇或脂环族二醇或其烷氧基化物,
d.2mol%至50mol%的聚醚多元醇,其官能度大于或等于2并且通过官能度大于或等于2(优选大于2)的多元醇g)在作为催化剂的胺的存在下的烷氧基化反应来制备,
e.0mol%至45mol%的聚醚多元醇,其官能度大于或等于2并且通过官能度大于或等于2的多元醇h)在除胺之外的催化剂的存在下的烷氧基化反应来制备,
f.0mol%至50mol%的多元醇,其官能度大于或等于2且选自甘油、三羟甲基丙烷、季戊四醇,
其中组分a)至f)的mol%总计为100%,并且至少200mmol、优选至少500mmol并且特别优选至少800mmol的OH官能度大于或等于2、优选大于或等于2.2的多元醇d)发生反应,以每kg聚酯多元醇计。
本发明还提供一种制备聚酯多元醇的方法,其中
·官能度大于或等于2的聚醚多元醇(d)通过官能度大于或等于2的多元醇(g)在作为催化剂的胺的存在下的烷氧基化反应来制备,
·官能度大于或等于2的聚醚多元醇(e)任选地通过官能度大于或等于2的多元醇(h)在除胺之外的催化剂的存在下的烷氧基化反应来制备,且
·2至50mol%的聚醚多元醇(d)和
·0至45mol%的聚醚多元醇(e)和
·0至50mol%的官能度大于或等于2且选自甘油、三羟甲基丙烷、季戊四醇的多元醇(f)与以下物质反应
·10至70mol%的二羧酸组合物,其包含
(a1)50mol%至100mol%的芳族二羧酸或芳族二羧酸的混合物,基于二羧酸组合物(a)计,
(a2)0mol%至50mol%的一种或多种脂族二羧酸,基于二羧酸组合物(a)计,和
·2mol%至30mol%的一种或多种脂肪酸和/或脂肪酸衍生物和
·10mol%至70mol%的一种或多种含有2至18个碳原子的脂族二醇或脂环族二醇或其烷氧基化物,
其中组分(a)至(f)的mol%总计为100%并且至少200mmol的OH官能度大于或等于2的多元醇(d)发生反应,以每kg聚酯多元醇计。
在本发明的一个实施方案中,组分a1)包括至少一种选自对苯二甲酸、对苯二甲酸二甲酯(DMT)、聚对苯二甲酸乙二醇酯(PET)、邻苯二甲酸、邻苯二甲酸酐(PAn)以及间苯二甲酸的物质。
在本发明的一个实施方案中,组分a1)包括至少一种选自对苯二甲酸、对苯二甲酸二甲酯(DMT)、聚对苯二甲酸乙二醇酯(PET)和邻苯二甲酸酐(PAn)的物质,优选选自对苯二甲酸、对苯二甲酸二甲酯(DMT)和聚对苯二甲酸乙二醇酯(PET)的物质,特别优选选自对苯二甲酸的物质。
本发明另外提供一种制备聚酯多元醇的方法,其中
·官能度大于或等于2的聚醚醇(d)通过官能度大于或等于2的多元醇(g)在作为催化剂的胺的存在下的烷氧基化反应来制备,
·官能度大于或等于2的聚醚醇(e)任选地通过官能度大于或等于2的多元醇(h)在除胺之外的催化剂的存在下的烷氧基化反应来制备,并且
·2至50mol%的聚醚醇(d)和
·0至45mol%的聚醚醇(e)以及
·0至50mol%的官能度大于或等于2且选自甘油、三羟甲基丙烷、季戊四醇的多元醇(f)与以下物质反应
·10至70mol%的二羧酸组合物,其包含
(a1)50至100mol%的至少一种选自对苯二甲酸二甲酯、聚对苯二甲酸乙二醇酯和邻苯二甲酸酐的物质,基于二羧酸组合物(a)计,
(a2)0至50mol%的一种或多种脂族二羧酸,基于二羧酸组合物(a)计,和
·2至30mol%的一种或多种脂肪酸和/或脂肪酸衍生物以及
·10至70mol%的一种或多种含有2至18个碳原子的脂族二醇或脂环族二醇或其烷氧基化物,
其中组分(a)至(f)的mol%分别总计为100%并且至少200mmol的OH官能度大于或等于2的多元醇(d)发生反应,以每kg聚酯多元醇计。
在本发明的一个实施方案中,所述脂族二羧酸a2)选自含有4至6个碳原子的脂族二羧酸。
在本发明的一个实施方案中,在二羧酸组合物a)中包含0mol%至30mol%、优选0mol%至10mol%、特别优选0mol%含量的组分a2)。
在本发明的一个实施方案中,组分b)以3mol%至20mol%、特别优选5mol%至18mol%的程度进入酯化产物中。
在本发明的一个实施方案中,组分c)以20mol%至60mol%、优选25mol%至55mol%、特别优选30mol%至40 mol%的程度进入酯化产物中。
在本发明的一个实施方案中,组分d)以2mol%至40mol%、优选2mol%至35mol%、特别优选20mol%至25mol%的程度进入酯化产物中。
在本发明的一个优选的实施方案中,d)中的胺催化剂选自DMEOA(二甲基乙醇胺)、咪唑和咪唑衍生物及其混合物,特别优选咪唑。
在本发明的一个实施方案中,e)中的除胺之外的催化剂选自KOH、双金属氰化物(DMC)催化剂、卡宾。
在本发明的一个实施方案中,所述脂族二醇或脂环族二醇c)选自乙二醇、二乙二醇、丙二醇、1,3-丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、2-甲基-1,3-丙二醇、3-甲基-1,5-戊二醇及其烷氧基化物。
在本发明的一个优选的实施方案中,所述脂族二醇c)为二乙二醇。
在本发明的一个实施方案中,所述脂肪酸或脂肪酸衍生物b)为基于可再生资源的脂肪酸或脂肪酸衍生物,选自蓖麻油、多羟基脂肪酸、蓖麻油酸、羟基改性的油、葡萄子油、黑枯茗油(black cumin oil)、南瓜仁油、琉璃苣籽油(borage seed oil)、大豆油、小麦胚芽油、菜籽油、葵花油、花生油、杏仁油(apricot kernel oil)、阿月浑子树油(pistachiooil)、甜杏仁油(almond oil)、橄榄油、澳洲坚果油、鳄梨油、沙棘油、芝麻油、麻籽油、榛子油、报春花油、野玫瑰油、红花油、核桃油、基于以下酸的羟基改性脂肪酸和脂肪酸酯:肉豆蔻酸、棕榈油酸、油酸、十八碳烯酸、岩芹酸(petroselic acid)、鳕油酸、芥酸、神经酸、亚油酸、α-亚麻酸和γ-亚麻酸、亚麻油酸(stearidonic acid)、花生四烯酸、二十碳五烯酸、二十二碳三烯炔酸(clupanodonic acid)以及二十二碳六烯酸(cervonic acid)。
在本发明的一个优选的实施方案中,所述脂肪酸或脂肪酸衍生物b)为油酸和/或大豆油和/或菜籽油,特别优选油酸。
在本发明的一个实施方案中,官能度大于或等于2的聚醚醇d)选自甘油、三羟甲基丙烷(TMP)、季戊四醇和聚乙二醇(PEG)及其混合物与环氧烷烃的反应产物。
在本发明的一个实施方案中,官能度大于或等于2的聚醚醇d)通过官能度大于或等于2的多元醇e)与环氧乙烷和/或环氧丙烷、优选与环氧乙烷反应来制备。
在本发明的一个实施方案中,官能度大于或等于2的聚醚醇d)包括甘油与环氧乙烷和/或环氧丙烷、优选与环氧乙烷的反应产物。
在本发明的一个实施方案中,官能度大于或等于2的聚醚醇d)包括三羟甲基丙烷与环氧乙烷和/或环氧丙烷、优选与环氧乙烷的反应产物。
在本发明的一个实施方案中,官能度大于或等于2的聚醚醇d)具有1250mg KOH/g至100mg KOH/g、优选950mg KOH/g至150mg KOH/g、特别优选800mg KOH/g至240mg KOH/g的OH值。
在本发明的一个优选的实施方案中,官能度大于或等于2的聚醚醇d)包括三羟甲基丙烷或甘油与环氧乙烷的反应产物,其中聚醚醇d)的OH值为500mg KOH/g至650mg KOH/g。
在本发明的一个特别优选的实施方案中,官能度大于或等于2的聚醚醇d)包括三羟甲基丙烷或甘油与环氧乙烷的反应产物,其中聚醚醇d)的OH值为500mg KOH/g至625mg KOH/g,且所述脂族二醇或脂环族二醇c)为二乙二醇且所述脂肪酸或脂肪酸衍生物为油酸。
在本发明的一个实施方案中,使用官能度大于2并且通过官能度大于或等于3的多元醇g)的烷氧基化反应来制备的聚醚醇d)。
为制备本发明的聚酯多元醇,在无催化剂或优选在酯化反应催化剂的存在下、有利地在惰性气体(例如氮气、一氧化碳、氦气、氩气等)的气氛中、在150至280℃、优选180至260℃的熔融温度下、任选在减压下,使有机的(例如脂族的并且优选芳族的)多元羧酸和/或其衍生物和多元醇缩聚至所需的酸值(有利地小于10,优选地小于2)。在一个优选的实施方案中,在大气压力下并且随后在低于500毫巴、优选40至400毫巴的压力下,使上述酯化反应混合物在上述温度下缩聚至80至20、优选40至20的酸值。可能的酯化反应催化剂为,例如金属、金属氧化物或金属盐形式的铁、镉、钴、铅、锌、锑、镁、钛和锡催化剂。但是,所述缩聚反应也可在液相中在稀释剂和/或夹带剂(例如苯、甲苯、二甲苯或氯苯)的存在下进行以蒸出作为共沸物的冷凝水。
为制备所述聚酯多元醇,有利地使有机多元羧酸和/或其衍生物和多元醇以1:1-2.1、优选1:1.05-2.0的摩尔比缩聚。
所得的聚酯多元醇优选具有1.8至4、特别是2至3的官能度,以及300至3000、优选400至1000并且特别是450至800的分子量。
在本发明的一个优选的实施方案中,本发明的聚酯多元醇具有大于或等于2、优选大于2.2的平均官能度。
此外,本发明还提供一种制备硬质PU泡沫的方法。
具体地,本发明提供一种通过以下物质的反应来制备硬质聚氨酯泡沫的方法:
A.至少一种有机的和/或改性有机的二异氰酸酯和/或多异氰酸酯
B.至少一种本发明的具体的聚酯多元醇,
C.任选地至少一种其他聚酯多元醇,
D.任选地至少一种聚醚多元醇和/或至少一种具有至少两个对异氰酸酯有反应活性的基团的其他化合物,
E.任选地至少一种增链剂和/或交联剂,
F.至少一种发泡剂,
G.至少一种催化剂以及
H.任选地至少一种其他助剂和/或至少一种添加剂和
I.任选地至少一种阻燃剂。
本发明还提供可通过本发明方法获得的硬质聚氨酯泡沫和硬质聚异氰脲酸酯泡沫,以及本发明的聚酯多元醇用于制备硬质聚氨酯泡沫或硬质聚异氰脲酸酯泡沫的用途。
为了通过本发明的方法制备硬质聚氨酯泡沫,除上述具体的聚酯多元醇外,还使用本身已知的形成组分,关于此可提供以下细节。
可用的有机的和/或改性有机的多异氰酸酯A)为本身已知的脂族多官能异氰酸酯、脂环族多官能异氰酸酯、芳脂族多官能异氰酸酯并且优选芳族多官能异氰酸酯。
具体的实例有:亚烷基基团中含有4至12个碳原子的亚烷基二异氰酸酯,例如十二烷1,12-二异氰酸酯、2-乙基四亚甲基1,4-二异氰酸酯、2-甲基五亚甲基1,5-二异氰酸酯、四亚甲基1,4-二异氰酸酯,并且优选六亚甲基1,6-二异氰酸酯;脂环族二异氰酸酯,例如环己烷1,3-二异氰酸酯和1,4-二异氰酸酯以及这些异构体的任意混合物、1-异氰酸基-3,3,5-三甲基-5-异氰酸基甲基环己烷(IPDI)、六氢甲苯2,4-二异氰酸酯和2,6-二异氰酸酯及其相应异构体的混合物、二环己基甲烷4,4’-二异氰酸酯、2,2’-二异氰酸酯和2,4’-二异氰酸酯及其相应异构体的混合物,并且优选芳族二异氰酸酯;以及多异氰酸酯例如甲苯2,4-二异氰酸酯和2,6-二异氰酸酯及其相应异构体的混合物、二苯基甲烷4,4’-二异氰酸酯、2,4’-二异氰酸酯和2,2’-二异氰酸酯及其相应异构体的混合物、二苯基甲烷4,4’-二异氰酸酯和2,2’-二异氰酸酯的混合物、聚苯基聚亚甲基聚异氰酸酯、二苯基甲烷2,4’-二异氰酸酯、2,4’-二异氰酸酯和2,2’-二异氰酸酯和聚苯基聚亚甲基聚异氰酸酯的混合物(粗MDI)以及粗MDI和甲苯二异氰酸酯的混合物。所述有机二异氰酸酯和多异氰酸酯可单独使用或以其混合物的形式使用。
优选的二异氰酸酯和多异氰酸酯为甲苯二异氰酸酯(TDI)和二苯基甲烷二异氰酸酯(MDI)并且特别是二苯基甲烷二异氰酸酯和聚亚苯基聚亚甲基聚异氰酸酯(聚合的MDI或PDMI)的混合物。
还通常使用改性的多官能异氰酸酯,即通过有机二异氰酸酯和/或多异氰酸酯的化学反应获得的产物。可提及的实例有包含酯基团、脲基团、缩二脲基团、脲基甲酸酯基团、碳二亚胺基团、异氰脲酸酯基团、脲二酮基团、氨基甲酸酯基团和/或氨基甲酸乙酯基团的二异氰酸酯和/或多异氰酸酯。
极特别优选使用聚合的MDI来制备硬质聚氨酯泡沫。
合适的其他聚酯多元醇C)可由例如含有2至12个碳原子的有机二羧酸(优选含有4-6个碳原子的脂族二羧酸)和含有2至12个碳原子、优选2至6个碳原子的多元醇、优选二醇来制备。可用的二羧酸为,例如:丁二酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、癸烷二羧酸、顺丁烯二酸、反丁烯二酸、邻苯二甲酸、间苯二甲酸、和对苯二甲酸。所述二羧酸可单独使用或彼此混合使用。还可用相应的二羧酸衍生物(例如含有1至4个碳原子的醇的二羧酸酯或二羧酸酐)代替游离的二羧酸。优选使用重量比例如为20-35:35-50:20-32的丁二酸、戊二酸和己二酸的二羧酸混合物并且特别是己二酸。二元醇和多元醇特别是二醇的实例有:乙二醇、二乙二醇、1,2-丙二醇或1,3-丙二醇、二丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,10-癸二醇、甘油、三羟甲基丙烷和季戊四醇。优选使用乙二醇、二乙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇或至少两种上述二醇的混合物,特别是1,4-丁二醇、1,5-戊二醇和1,6-己二醇的混合物。也可使用衍生自内酯(例如ε-己内酯)或羟基羧酸(例如ω-羟基己酸)的聚酯多元醇。
还可伴随使用通过已知方法制备的聚醚多元醇D),所述已知方法例如由一种或多种亚烷基中含有2至4个碳原子的环氧烷烃通过使用碱金属氢氧化物(例如氢氧化钠或氢氧化钾)或碱金属醇盐(例如甲醇钠、乙醇钠或乙醇钾或异丙醇钾)作为催化剂并且加入至少一种含有2至8个、优选2至6个活泼氢原子的起始分子进行阴离子聚合,或通过使用路易斯酸(例如五氯化锑、三氟化硼乙醚等)、或漂白土作为催化剂进行阳离子聚合。
合适的环氧烷烃为例如四氢呋喃、1,3-环氧丙烷、1,2-环氧丁烷或2,3-环氧丁烷、氧化苯乙烯并且优选环氧乙烷和1,2-环氧丙烷。这些环氧烷烃可单独使用、连续使用或作为混合物使用。优选的环氧烷烃为环氧丙烷和环氧乙烷,特别优选环氧乙烷。
可用的起始分子为,例如:水;有机二羧酸,例如丁二酸、己二酸、邻苯二甲酸和对苯二甲酸;在烷基基团中含有1至4个碳原子的未取代的或被N-单烷基、N,N-二烷基和N,N’-二烷基取代的脂族和芳族二胺,例如未取代的或被单烷基和二烷基取代的乙二胺、二亚乙基三胺、三亚乙基四胺、1,3-丙二胺、1,3-或1,4-丁二胺、1,2-、1,3-、1,4-、1,5-和1,6-六亚甲基二胺、苯二胺、2,3-、2,4-和2,6-甲苯二胺和4,4’-、2,4’-和2,2’-二氨基二苯基甲烷。
其他可用的起始分子为:烷醇胺(例如乙醇胺、N-甲基乙醇胺和N-乙基乙醇胺)、二烷醇胺(例如二乙醇胺、N-甲基二乙醇胺和N-乙基二乙醇胺)和三烷醇胺(例如三乙醇胺)以及氨。优选使用二元醇或多元醇(例如乙二醇、1,2-和1,3-丙二醇、二乙二醇、二丙二醇、1,4-丁二醇、1,6-己二醇、甘油、三羟甲基丙烷、季戊四醇、山梨醇和蔗糖。
所述聚醚多元醇——优选聚氧乙烯多元醇——具有优选2至6且特别是2至5的官能度以及300至3000、优选300至2000并且特别是400至1000的分子量。
其他合适的聚醚多元醇为聚合物改性的聚醚多元醇,优选接枝聚醚多元醇,特别是基于苯乙烯和/或丙烯腈的聚醚多元醇,其通过丙烯腈、苯乙烯或优选苯乙烯和丙烯腈的混合物(例如以90:10至10:90,优选70:30至30:70的重量比)的原位聚合来制备,有利地在上述聚醚多元醇中使用类似于记载于德国专利文件11 11 394、12 22 669(US 3,304,273,3,383,351,3,523,093)、11 52 536(GB 10 40 452)和11 52 537(GB 987,618)中的方法,以及通常包含1至50重量%、优选2至25重量%含量的例如含有键合的叔氨基和/或三聚氰胺的聚脲、聚酰肼、聚氨酯作为分散相的聚醚多元醇分散体,其记载于例如EP-B 011 752(US 4,304,708)、US-A,4,374,209和DE-A,32 31 497中。
如所述聚酯多元醇,聚醚多元醇可单独使用或以混合物的形式使用。其也可与接枝聚醚多元醇或聚酯多元醇以及与含羟基的聚酯酰胺、聚缩醛、聚碳酸酯和/或聚醚多元胺混合。
可用的含羟基的聚缩醛为,例如可由乙二醇类(例如二乙二醇、三乙二醇、4,4’-二羟基乙氧基二苯基二甲基甲烷、己二醇)和甲醛制备的化合物。合适的聚缩醛也可通过环状缩醛的聚合制备。
可用的含羟基的聚碳酸酯为可通过例如二醇类(例如1,3-丙二醇、1,4-丁二醇和/或1,6-己二醇、二乙二醇、三乙二醇或四乙二醇)与碳酸二芳酯(例如碳酸二苯酯)、碳酸亚烷酯或光气的反应而制备的本身已知的类型。
所述聚酯酰胺包括,例如,由多元的饱和的和/或不饱和的羧酸或其酸酐与多元的饱和的和/或不饱和的氨基醇或多元醇和氨基醇和/或多元胺的混合物获得的主要为线性的缩合物。
合适的聚醚多元胺可通过已知方法由上述聚醚多元醇制备。可提及的实例有聚氧化亚烷基多元醇的氰烷基化反应和随后的所形成的腈的氢化反应(US 3 267 050)或聚氧化亚烷基多元醇与胺或氨在氢和催化剂的存在下的部分或完全的胺化反应(DE 12 15 373)。
硬质聚氨酯泡沫可使用增链剂和/或交联剂(E)制备。但是,增链剂、交联剂或任选地其混合物的添加可证明对于改性机械性能(例如硬度)是有利的。使用分子量小于400、优选60至300的二元醇和/或三元醇作为增链剂和/或交联剂。可能作为起始分子的有例如含有2至14个、优选4至10个碳原子的脂族二元醇、脂环族二元醇和/或芳脂族二元醇(例如乙二醇、1,3-丙二醇、1,10-癸二醇、邻二羟基环己烷、间二羟基环己烷、对二羟基环己烷、二乙二醇、二丙二醇并且优选1,4-丁二醇、1,6-己二醇和二(2-羟乙基)氢醌)、三元醇(例如1,2,4-、1,3,5-三羟基环己烷、甘油和三羟甲基丙烷)以及基于环氧乙烷和/或1,2-环氧丙烷和上述二元醇和/或三元醇的低分子量的含羟基的聚环氧烷烃。
可用的含有至少两个对异氰酸酯有反应活性的基团(即含有至少两个对异氰酸酯基有反应活性的氢原子)的其他化合物(D)特别为含有两个以上选自OH基团、SH基团、NH基团、NH2基团、CH-酸基团(例如β-二酮基)的活性基团的化合物。
如果使用增链剂、交联剂或其混合物来制备硬质聚氨酯泡沫,则其有利地以0至20重量%、优选0.5至5重量%的量使用,基于组分B)的重量计。
用于制备所述硬质聚氨酯泡沫的发泡剂F)优选包括水、甲酸及其混合物。它们与异氰酸酯基反应形成二氧化碳并且在甲酸的情况下形成二氧化碳和一氧化碳。此外,可使用物理发泡剂如低沸点的烃。合适的物理发泡剂为对有机的、改性的或未改性的多异氰酸酯具有惰性并且具有在大气压力下沸点低于100℃、优选低于50℃的液体,以使其在放热的加聚反应条件下蒸发。可优选使用的此类液体的实例有烷烃,例如庚烷、己烷、正戊烷和异戊烷,优选以下物质的工业混合物:正戊烷和异戊烷、正丁烷和异丁烷和丙烷;环烷烃,例如环戊烷和/或环己烷;醚类,例如呋喃、二甲醚和乙醚;酮类,例如丙酮和甲基乙基酮;羧酸烷基酯,例如甲酸甲酯、草酸二甲酯和乙酸乙酯;以及卤代烃,例如二氯甲烷、二氯一氟甲烷、二氟甲烷、三氟甲烷、二氟乙烷、四氟乙烷、氯二氟乙烷、1,1-二氯-2,2,2-三氟乙烷、2,2-二氯-2-氟乙烷和七氟丙烷。还可使用这些低沸点液体彼此的混合物和/或与其他取代的或未取代的烃的混合物。有机羧酸例如甲酸、乙酸、草酸、蓖麻油酸和含羧基的化合物也适用。
优选使用水、甲酸、氯二氟甲烷、氯二氟乙烷、二氯氟乙烷、所有的戊烷异构体及其混合物、环己烷和至少两种这些发泡剂的混合物,例如水和环己烷的混合物、氯二氟甲烷和1-氯-2,2-二氟乙烷和任选地水的混合物。
这些发泡剂完全地或者部分地溶解于多元醇组分(即B+C+E+F+G+H+I)中或通过静态混合器在多元醇组分的发泡前才加入。水或甲酸通常完全或部分地溶解于多元醇组分和物理发泡剂(例如戊烷)以及任选地“在线(on-line)”引入的化学发泡剂的残留物中。
所用的发泡剂或发泡剂混合物的量为1重量%至45重量%,优选1重量%至30重量%,特别优选1.5重量%至20重量%,各自基于组分B)至G)的总和计。
如果用水作为发泡剂,则优选将其以0.2重量%至5重量%的量加入所述形成组分B)中,基于形成组分B)计。加入的水可与所述其他发泡剂结合使用。
用于制备所述硬质聚氨酯泡沫的催化剂G)特别为使组分B)和任选地C)的含有活泼氢原子、特别是含有羟基的化合物与有机的、改性的或未改性的多异氰酸酯A)的反应剧烈加速的化合物。
有利地使用碱性聚氨酯催化剂,例如叔胺,例如三乙胺、三丁胺、二甲基苄胺、二环己基甲胺、二甲基环己胺、双(N,N-二甲氨基乙基)醚、双(二甲氨基丙基)脲、N-甲基吗啉或N-乙基吗啉、N-环己基吗啉、N,N,N’,N’-四甲基乙二胺、N,N,N’,N’-四甲基丁二胺、N,N,N’,N’-四甲基己-1,6-二胺、五甲基二亚乙基三胺、二甲基哌嗪、N-二甲氨基乙基哌啶、1,2-二甲基咪唑、1-氮杂双环[2.2.0]辛烷、1,4-二氮杂双环[2.2.0]辛烷(Dabco);和烷醇胺化合物,例如三乙醇胺、三异丙醇胺、N-甲基二乙醇胺和N-乙基二乙醇胺、二甲氨基乙醇、2-(N,N-二甲氨基乙氧基)乙醇;N,N’,N”–三(二烷氨基烷基)六氢三嗪,例如N,N’,N”-三(二甲氨基丙基)-s-六氢三嗪、和三亚乙基二胺。但是,金属盐例如氯化亚铁(II)、氯化锌、辛酸铅并且优选锡盐例如二辛酸锡、二乙基己酸锡和二月桂酸二丁基锡以及特别是叔胺和有机锡盐的混合物也适用。
其他可能的催化剂有:脒,例如2,3-二甲基-3,4,5,6-四氢嘧啶、氢氧化四烷基铵例如氢氧化四甲铵、碱金属氢氧化物例如氢氧化钠和碱金属醇盐例如甲醇钠和异丙醇钾以及含有10至20个碳原子和任选地侧OH基的长链脂肪酸的碱金属盐。优选使用0.001重量%至5重量%、特别是0.05重量%至2重量%的催化剂或催化剂结合物,基于组分B)的重量计。还可使反应在无催化剂下进行。在这种情况下,利用胺引发的多元醇的催化活性。
在发泡过程中,如果使用相对大量过量的多异氰酸酯,则用于过量的NCO基彼此的三聚反应的其他合适的催化剂有:形成异氰脲酸酯基的催化剂,例如单独的或与叔胺结合的铵盐或碱金属盐。异氰脲酸酯的形成使生成阻燃的PIR泡沫,其优选用于例如建筑和建筑物的绝缘板或夹层元件中的工业硬质泡沫。在下文中,术语聚氨酯还将包括PIR泡沫的泡沫类。
关于上述和其他原料的其他信息可见于技术文献中,例如Kunststoffhandbuch,第VII卷,Polyurethane,Carl Hanser VerlagMunich,Vienna,第一版,第二版和第三版1966,1983和1993。
可任选向反应混合物中添加其他助剂和/或添加剂H)来制备硬质聚氨酯泡沫。可提及的实例有,表面活性物质、稳泡剂、孔调节剂、填料、染料、颜料、阻燃剂、水解抑制剂、抑制真菌物质和抑制细菌物质。
可用的表面活性物质为,例如,用于辅助原料均化并且还可适于调节聚合物的孔结构的化合物。可提及的实例有,乳化剂例如蓖麻油硫酸盐的钠盐或脂肪酸的钠盐或脂肪酸与胺的盐,例如油酸二乙胺、硬脂酸二乙醇胺、蓖麻酸二乙醇胺;磺酸盐,例如十二烷基苯磺酸或二萘基甲烷二磺酸和蓖麻油酸的碱金属盐或铵盐;稳泡剂例如硅氧烷-氧化烯烃共聚物和其他的有机聚硅氧烷、乙氧基化烷基酚、乙氧基化脂肪醇、石蜡油、蓖麻油酯或蓖麻油酸酯、土耳其红油和花生油;以及孔调节剂,例如石蜡、脂肪醇和二甲基聚硅氧烷。上述具有聚氧化烯烃和氟代烷烃基团作为侧基的低聚丙烯酸酯也适于改善乳化作用、孔结构和/或用于稳定泡沫。所述表面活性物质通常以0.01重量%至10重量%的量使用,基于100重量%的组分B)计。
就本发明而言,填料(特别是增强填料)为常规的有机和无机填料、增强材料、增重剂、用于改善油漆和涂料组合物的磨损性能的制剂等,它们本身是已知的。具体实例有:无机填料例如硅质矿物,例如层状硅酸盐例如叶蛇纹石、蛇纹石、角闪石、闪石、纤蛇纹石(chrisotile)和滑石;金属氧化物例如高岭土、氧化铝、二氧化钛和氧化铁;金属盐,例如白垩、重晶石和无机颜料例如硫化镉和硫化锌以及玻璃等。优选使用高岭土(瓷土)、硅酸铝和硫酸钡与硅酸铝的共沉淀物以及天然的和合成的纤维矿物例如钙硅石、金属纤维且特别是各种长度的玻璃纤维,所述玻璃纤维可涂有胶料。可用的有机填料为,例如:碳、三聚氰胺、松香、环戊二烯基树脂和接枝聚合物以及纤维素纤维、聚酰胺、聚丙烯腈、聚氨酯、基于芳族和/或脂族二羧酸酯的聚酯纤维并且特别是碳纤维。
所述无机的和有机的填料可单独使用或作为混合物使用并且有利地将其以0.5重量%至50重量%、优选1重量%至40重量%的量加入反应混合物中,基于组分A)至C)的重量计,但天然和合成纤维的垫、非织造布、和机织布的含量可达到最高达80重量%的值。
作为阻燃剂I),通常可使用现有技术已知的阻燃剂。合适的阻燃剂为,例如,不可掺入(unincorporatable)的溴化物、溴化酯、溴化醚(lxol)或溴化醇例如二溴新戊醇、三溴新戊醇和PHT-4-二醇以及氯化磷酸酯例如磷酸三(2-氯乙基)酯、磷酸三(2-氯丙基)酯、磷酸三(1,3-二氯丙基)酯、磷酸三甲苯酯、磷酸三(2,3-二溴丙基)酯、亚乙基二磷酸四(2-氯乙基)酯、甲基膦酸二甲酯、二乙醇氨基甲基膦酸二乙酯以及市售的含卤素的阻燃剂多元醇。可使用磷酸酯或膦酸酯作为其他的液体阻燃剂,例如乙烷膦酸二乙酯(DEEP)、磷酸三乙酯(TEP)、丙基膦酸二甲酯(DMPP)、甲苯基磷酸二苯酯(DPK)及其他。
除上述阻燃剂外,还可使用无机或有机的阻燃剂例如红磷、包含红磷的制剂、水合氧化铝、三氧化锑、氧化砷、多磷酸铵和硫酸钙、可膨胀石墨或氰尿酸衍生物例如三聚氰胺、或至少两种阻燃剂——例如多磷酸铵和三聚氰胺和任选地玉米淀粉或多磷酸铵、三聚氰胺和可膨胀石墨和/或任选地芳族聚酯——的混合物来使所述硬质聚氨酯泡沫耐燃。
通常,已经发现使用5重量%至150重量%、优选10重量%至100重量%的所提及的阻燃剂是有利的,基于组分B)计。
关于上述其他常规助剂和添加剂的其他信息可见于技术文献中,例如J.H.Saunders和K.C.Frisch的专著―High Polymers‖第XVI卷,Polyurethanes,第1部分和第2部分,Interscience Publishers 1962和1964,或Kunststoff-Handbuch,Polyurethane,第VII卷,Hanser-Verlag,Munich,Vienna,第一版和第二版,1966和1983。
为制备本发明的硬质聚氨酯泡沫,使有机的和/或改性有机的多异氰酸酯A)、本发明的特定的聚酯多元醇B)和任选地聚醚多元醇和/或具有至少两个对异氰酸酯有反应活性的基团的其他化合物D)和任选地增链剂和/或交联剂E)以下述量反应:多异氰酸酯A)的NCO基与组分B)和任选地C)和D)至G)的活泼氢原子的总和的当量比为1-6:1、优选1.1-5:1并且特别为1.2-3.5:1。
所述硬质聚氨酯泡沫有利地通过一步法制备,例如在开放或密闭模具——例如金属模具——中通过高压或低压技术制备。连续施加反应混合物至合适的传送带来制造板材(panel)的也是惯用的。
起始化合物在15℃至90℃、优选20℃至60℃以及特别为20℃至35℃的温度下混合,然后将其加入开放模具中或任选地在升高的压力下将其加入密闭模具中、或对连续工作站而言将其施加到容纳反应混合物的带上。如上所述,可通过搅拌器或搅拌螺杆机械地进行混合。模具温度有利地为20℃至110℃、优选30℃至70℃并且特别为40℃至60℃。
通过本发明方法制备的硬质聚氨酯泡沫具有15g/l至300g/l、优选20g/l至100g/l、并且特别是25g/l至60g/l的密度。
实施例
通过以下实施例对本发明进行说明,这些实施例仅用来说明本发明的某些方面并且绝不旨在限制本发明的范围。
制备各种聚酯多元醇:
制备聚酯多元醇的通用方法
将二羧酸、脂肪衍生物的脂肪酸、脂族二醇或脂环族二醇或其烷氧基化物和更高官能的多元醇加入配有机械搅拌器、温度计、蒸馏塔以及氮气入口管的4升圆底烧瓶中。加入300ppm作为催化剂的四丁基钛后,将混合物搅拌并加热至240℃,同时将生成的水连续蒸出。该反应在400毫巴下进行。得到具有≤1mg KOH/g的酸值的聚酯多元醇。
胺催化制备聚醚多元醇(权利要求1的(d)中的聚醚多元醇)的通用方法。
将配有搅拌器、夹套加热和冷却装置、用于包含环氧烷烃的固体物质和液体物质的计量设备以及用于引入氮气的设备和真空系统的960l压力反应器加热至80℃进行干燥。加入145.4kg甘油和1000g 50%浓度的咪唑水溶液并且用氮气惰化反应器三次。开动搅拌器并将反应器加热至120℃。随后计量加入354.0kg环氧乙烷(初始压力:2.5巴)。在120℃下反应1.5小时后,释放剩余压力并在减压下将混合物解吸(strip)30分钟。得到485.3kg具有以下规格的多元醇:
羟基值 527mg KOH/g
粘度 25℃下275mPas
水含量 0.006%
对比实施例1
采用制备聚酯多元醇的通用方法,用572.4g对苯二甲酸、316.3g油酸、447.9g二乙二醇和907.8g经后处理的聚醚多元醇A,所述聚醚多元醇A基于甘油和环氧乙烷且OH官能度为3、羟基值为540mgKOH/g以及残留碱度为<500mg KOH/g并且用KOH催化制备。得到OH官能度为2.49且羟基值为241mg KOH/g的聚酯多元醇。
对比实施例2
采用制备聚酯多元醇的通用方法,用601.9g对苯二甲酸、352.9g大豆油、461.4g二乙二醇和814.3g经后处理的聚醚多元醇A,所述聚醚多元醇A基于甘油和环氧乙烷且OH官能度为3以及羟基值为540mgKOH/g并且用KOH催化制备。得到OH官能度为2.49且羟基值为249mg KOH/g的聚酯多元醇。
对比实施例3
采用制备聚酯多元醇的通用方法,用668.2g对苯二甲酸、356.2g大豆油、501.6g二乙二醇和719.0g经后处理的聚醚多元醇B,所述聚醚多元醇B基于三羟甲基丙烷和环氧乙烷且OH官能度为3以及羟基值为610mg KOH/g并且用KOH催化制备。得到OH官能度为2.49且羟基值为246mg KOH/g的聚酯多元醇。
对比实施例4
采用制备聚酯多元醇的通用方法,用214.3g对苯二甲酸、54.6g油酸、218.9g二乙二醇和162.1g的未中和的聚醚多元醇A,所述聚醚多元醇A基于甘油和环氧乙烷且OH官能度为3以及羟基值为540mgKOH/g并且用KOH催化制备。得到2相产物,其在KOH中和后未得到均匀产物。
本发明的实施例1
采用制备聚酯多元醇的通用方法,用572.4g对苯二甲酸、316.3g油酸、447.9g二乙二醇和907.8g的聚醚多元醇C,所述聚醚多元醇C基于甘油和环氧乙烷且OH官能度为3以及羟基值为540mg KOH/g并且通过用于制备聚醚多元醇的通用方法制备。得到OH官能度为2.49且羟基值为252mg KOH/g的聚酯多元醇。
本发明的实施例2
采用制备聚酯多元醇的通用方法,用601.9g对苯二甲酸、352.9g大豆油、461.4g二乙二醇和814.3g的聚醚多元醇C,所述聚醚多元醇C基于甘油和环氧乙烷且OH官能度为3以及羟基值为540mg KOH/g并且通过用于制备聚醚多元醇的通用方法制备。得到OH官能度为2.49且羟基值为248mg KOH/g的聚酯多元醇。
表1:
表1示出了通过本发明的方法制备的聚酯多元醇未呈现出与常规产物(对比实施例)的显著差异。
测量方法
通过从1m×2m的泡沫样品移出覆盖层并任选地评估该表面来进行硬质PUR泡沫的表面性质的定性评估。
加工性的测定
通过检测加工过程中的泡沫形成来测定其加工性。在泡沫表面爆裂并因此使表面裂开的大发泡剂气泡被称为“爆裂”(“blow-out”)并且该体系不能以无故障的方式进行加工。如果没有观察到这种不令人满意的表现,则所述加工就是无故障的。
厚度
为测定发泡后的元件厚度,通过双带法(double belt process)制备具有0.05mm厚度的铝箔作为覆盖层材料的夹层元件并且在制备后5分钟在元件的中部测定元件厚度。
硬质聚氨酯泡沫的制备(变型1):
将异氰酸酯和对异氰酸酯有反应活性的组分连同发泡剂、催化剂和所有的其他添加剂以100:190的多元醇对异氰酸酯的恒定混合比进行发泡。
多元醇组分:
异氰酸酯组分:
190重量份的M50(25℃下粘度约500mPa*s的聚合的亚甲基二(苯基二异氰酸酯)(PMDI))
通过双带法制备50mm厚的夹层元件。通过改变含水量在6.5份的恒定戊烷含量下将泡沫密度设为38+/-1g/l。还通过改变二甲基环己胺的比例将纤维时间(fiber time)设为25+/-1秒。
结果总结于表2和表3中
表2:通过双带法制备50 mm厚夹层元件的实验结果
聚酯多元醇: | 对比实施例1 | 本发明的实施例1 |
视觉评估 | 好 | 好 |
加工 | 无故障 | 无故障 |
表3:通过双带法制备50mm厚夹层元件的实验结果
聚酯多元醇: | 对比实施例2 | 本发明的实施例2 |
视觉评估 | 好 | 好 |
加工 | 无故障 | 无故障 |
表2和表3示出了通过本发明方法制备的硬质聚氨酯泡沫保持了良好的加工性能。
此外,通过使用上述体系的双带法制备170mm厚的夹层元件。通过改变含水量在6.5份的恒定戊烷含量下将泡沫密度设为38+/-1g/l。还通过改变二甲基环己胺的比例将纤维时间设为40+/-1秒。
结果总结于表4和表5中:
表4:通过双带法制备170mm厚夹层元件的实验结果
聚酯多元醇: | 对比实施例1 | 本发明的实施例1 |
发泡后的元件厚度 | 180mm | 180mm |
表5:通过双带法制备170mm厚夹层元件的实验结果
聚酯多元醇: | 对比实施例2 | 本发明的实施例2 |
发泡后的元件厚度 | 182mm | 181mm |
表4和表5示出了通过使用本发明的聚酯多元醇保持了聚氨酯体系的尺寸稳定性。
硬质聚氨酯泡沫的制备(变型2):
此外,根据以下制备硬质聚氨酯泡沫的方法通过双带法制备试验板(变型2)。
将异氰酸酯和对异氰酸酯有反应活性的组分连同发泡剂、催化剂和所有的其他添加剂以100:170的多元醇组分对异氰酸酯组分的恒定混合比进行发泡。
多元醇组分:
异氰酸酯组分:
170重量份的M50
通过双带法制备50mm厚的夹层元件。通过改变戊烷含量在恒定的甲酸含量下将泡沫密度设为41+/-1g/l。还通过改变双(2-二甲氨基乙基)醚(二丙二醇中70重量%)的比例将纤维时间设为25+/-1秒。
如上所述,将所述组分一起发泡。表面评估和加工性的结果总结于表6和表7中。
表6:通过双带法制备50mm厚夹层元件的实验结果
聚酯多元醇: | 对比实施例1 | 本发明的实施例1 |
视觉评估 | 好 | 好 |
加工 | 无故障 | 无故障 |
表7:通过双带法制备50mm厚夹层元件的实验结果
聚酯多元醇: | 对比实施例2 | 根据本发明的实施例2 |
视觉评估 | 好 | 好 |
加工 | 无故障 | 无故障 |
表6和表7示出了通过本发明方法制备的硬质聚异氰脲酸酯泡沫保持了良好的加工性能。
此外,通过使用上述体系的双带法制备170mm厚的夹层元件。通过改变戊烷含量在恒定的甲酸含量下将泡沫密度设为41+/-1g/l。还通过改变双(2-二甲氨基乙基)醚(二丙二醇中70重量%)的比例将纤维时间设为40+/-1秒。
结果总结于表8和表9中:
表8:通过双带法制备170mm厚夹层元件的实验结果
聚酯多元醇: | 对比实施例1 | 本发明的实施例1 |
发泡后的元件厚度 | 180mm | 180mm |
表9:通过双带法制备170mm厚夹层元件的实验结果
聚酯多元醇: | 对比实施例2 | 本发明的实施例2 |
发泡后的元件厚度 | 182mm | 181mm |
表8和表9示出了通过使用本发明的聚酯多元醇可保持聚氨酯体系的尺寸稳定性。
Claims (11)
1.一种制备聚酯多元醇的方法,其中
·官能度大于或等于2的聚醚醇(d)通过官能度大于或等于2的多元醇(g)在作为催化剂的胺的存在下的烷氧基化反应来制备,
·官能度大于或等于2的聚醚醇(e)任选地通过官能度大于或等于2的多元醇(h)在除胺之外的催化剂的存在下的烷氧基化反应来制备,并且
·2至50mol%的聚醚醇(d)和
·0至45mol%的聚醚醇(e)以及
·0至50mol%的官能度大于或等于2且选自甘油、三羟甲基丙烷、季戊四醇的多元醇(f)与以下物质反应
·10至70mol%的二羧酸组合物,其包含
(a1)50至100mol%的芳族二羧酸或芳族二羧酸的混合物,基于二羧酸组合物(a)计,
(a2)0至50mol%的一种或多种脂族二羧酸,基于二羧酸组合物(a)计,和
·2至30mol%的一种或多种脂肪酸和/或脂肪酸衍生物以及
·10至70mol%的一种或多种含有2至18个碳原子的脂族二醇或脂环族二醇或其烷氧基化物,
其中组分(a)至(f)的mol%分别总计为100%并且至少200mmol的OH官能度大于或等于2的多元醇(d)发生反应,以每kg聚酯多元醇计。
2.权利要求1的制备聚酯多元醇的方法,其中所述芳族二羧酸(a1)选自对苯二甲酸、邻苯二甲酸和间苯二甲酸。
3.一种制备聚酯多元醇的方法,其中
·官能度大于或等于2的聚醚醇(d)通过官能度大于或等于2的多元醇(g)在作为催化剂的胺的存在下的烷氧基化反应来制备,
·官能度大于或等于2的聚醚醇(e)任选地通过官能度大于或等于2的多元醇(h)在除胺之外的催化剂的存在下的烷氧基化反应来制备,并且
·2至50mol%的聚醚醇(d)和
·0至45mol%的聚醚醇(e)以及
·0至50mol%的官能度大于或等于2且选自甘油、三羟甲基丙烷、季戊四醇的多元醇(f)与以下物质反应
·10至70mol%的二羧酸组合物,其包含
(a1)50至100mol%的至少一种选自对苯二甲酸二甲酯、聚对苯二甲酸乙二醇酯和邻苯二甲酸酐的物质,基于二羧酸组合物(a)计,
(a2)0至50mol%的一种或多种脂族二羧酸,基于二羧酸组合物(a)计,和
·2至30mol%的一种或多种脂肪酸和/或脂肪酸衍生物以及
·10至70mol%的一种或多种含有2至18个碳原子的脂族二醇或脂环族二醇或其烷氧基化物,
其中组分(a)至(f)的mol%分别总计为100%并且至少200mmol的OH官能度大于或等于2的多元醇(d)发生反应,以每kg聚酯多元醇计。
4.权利要求1至3中任一项的制备聚酯多元醇的方法,其中所述脂族二羧酸(a2)选自含有4至6个碳原子的脂族二羧酸。
5.权利要求1至3中任一项的制备聚酯多元醇的方法,其中所述脂肪酸和/或脂肪酸衍生物(b)选自油酸、大豆油和菜籽油。
6.权利要求1至3中任一项的制备聚酯多元醇的方法,其中所述含有2至18个碳原子的脂族二醇或脂环族二醇或其烷氧基化物(c)为二乙二醇。
7.权利要求1至3中任一项的制备聚酯多元醇的方法,其中所述多元醇(g)和所述多元醇(h)各自独立地选自甘油、三羟甲基丙烷、季戊四醇、聚乙二醇及其混合物。
8.权利要求1至3中任一项的制备聚酯多元醇的方法,其中所述多元醇g)具有大于2的官能度。
9.权利要求1至3中任一项的制备聚酯多元醇的方法,其中(d)中的胺催化剂选自二甲基乙醇胺、咪唑、咪唑衍生物及其混合物。
10.权利要求1至3中任一项的制备聚酯多元醇的方法,其中(e)中的除胺之外的催化剂选自KOH、双金属氰化物催化剂、卡宾。
11.权利要求1至3中任一项的制备聚酯多元醇的方法,其中所述聚酯多元醇具有大于或等于2的平均官能度。
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EP11155611A EP2492297A1 (de) | 2011-02-23 | 2011-02-23 | Polyesterpolyole auf Basis aromatischer Dicarbonsäuren und daraus hergestellte Polyurethanhartschäume |
PCT/EP2012/052822 WO2012113737A1 (de) | 2011-02-23 | 2012-02-20 | Polyesterpolyole auf basis aromatischer dicarbonsäuren und daraus hergestellte polyurethanhartschäume |
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US8895636B2 (en) | 2012-01-02 | 2014-11-25 | Basf Se | Producing rigid polyurethane foams and rigid polyisocyanurate foams |
HUE027908T2 (en) * | 2012-01-02 | 2016-11-28 | Basf Se | A method for producing polyurethane hard foam and polyisocyanurate hard foam |
US9193862B2 (en) | 2012-02-22 | 2015-11-24 | Basf Se | Blends for composite materials |
HUE036775T2 (hu) * | 2012-05-30 | 2018-07-30 | Basf Se | Poliuretán-keményhabok elõállítására szolgáló poliészterolok |
US9475220B2 (en) | 2013-02-13 | 2016-10-25 | Basf Se | Process for producing composite elements |
CN103641981B (zh) * | 2013-12-20 | 2015-09-09 | 山东一诺威新材料有限公司 | 连续式生产聚氨酯板材用高阻燃组合聚醚及其制备方法 |
WO2018138048A1 (de) * | 2017-01-25 | 2018-08-02 | Basf Se | Kälteflexible polyurethanformulierung |
WO2019079597A1 (en) | 2017-10-18 | 2019-04-25 | Talaco Holdings, LLC | POLYETHER POLYESTER AROMATIC POLYOLS DERIVED FROM POLYETHYLENE TEREPHTHALATES, POLYURETHANES MADE THEREFROM AND USEFUL MATERIALS COMPRISING THE SAME |
US11578165B2 (en) | 2019-01-21 | 2023-02-14 | Talaco Holdings, LLC | Methods of making foams exhibiting desired properties from aromatic polyester polyether polyols derived from polyethylene terephthalates and foams made therefrom |
CN114031759A (zh) * | 2021-12-10 | 2022-02-11 | 盐城市恒丰海绵有限公司 | 一种不饱和脂肪二元酸基聚酯多元醇及其制备方法 |
WO2024130080A1 (en) * | 2022-12-16 | 2024-06-20 | Dow Global Technologies Llc | Isocyanate reactive component with enhanced hydrocarbon compatibility |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3138562A (en) * | 1959-05-23 | 1964-06-23 | Bayer Ag | Cellular polyurethane plastics |
EP2177555A2 (de) * | 2008-10-16 | 2010-04-21 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyetheresterpolyolen |
WO2010043624A2 (de) * | 2008-10-15 | 2010-04-22 | Basf Se | Polyesterpolyole auf basis von terephthalsäure |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1003714B (de) | 1956-01-25 | 1957-03-07 | Glanzstoff Ag | Verfahren zum Abbau von Polyaethylenterephthalat zu Terephthalsaeuredimethylester |
BE598847A (zh) | 1960-01-05 | |||
US3304273A (en) | 1963-02-06 | 1967-02-14 | Stamberger Paul | Method of preparing polyurethanes from liquid, stable, reactive, filmforming polymer/polyol mixtures formed by polymerizing an ethylenically unsaturated monomer in a polyol |
US3523093A (en) | 1961-11-28 | 1970-08-04 | Paul Stamberger | Method of producing polyurethanes by reacting polyisocyanate with a preformed polymer resulting from polymerization of ethylenically unsaturated monomers |
GB1022434A (en) | 1961-11-28 | 1966-03-16 | Union Carbide Corp | Improvements in and relating to polymers |
DE1152536B (de) | 1962-03-30 | 1963-08-08 | Bayer Ag | Verfahren zur Herstellung Urethangruppen enthaltender Schaumstoffe |
US3267050A (en) | 1962-05-21 | 1966-08-16 | Union Carbide Corp | Foamed organic polyisocyanate-amine reaction products |
DE1152537B (de) | 1962-06-02 | 1963-08-08 | Bayer Ag | Verfahren zur Herstellung von homogenen, Urethangruppen aufweisenden Kunststoffen |
DE1215373B (de) | 1962-07-12 | 1966-04-28 | Bayer Ag | Verfahren zur Herstellung von linearen oder verzweigten Polypropylenglykolaethern mit Aminogruppen |
GB1152537A (en) | 1967-09-29 | 1969-05-21 | Shell Int Research | The Manufacture of Flame-Retardant Polymers, and the Resulting Polymers and Use thereof |
DE2850609A1 (de) | 1978-11-22 | 1980-06-12 | Basf Ag | Verfahren zur herstellung von stabilen fuellstoff-polyol-dispersionen |
US4374209A (en) | 1980-10-01 | 1983-02-15 | Interchem International S.A. | Polymer-modified polyols useful in polyurethane manufacture |
DE3231497A1 (de) | 1982-08-25 | 1984-03-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von kompakten, waermebestaendigen urethan- und isocyanuratgruppen enthaltenden kunststoffen |
US5051528A (en) | 1990-04-24 | 1991-09-24 | Eastman Kodak Company | Recovery process for ethylene glycol and dimethylterephthalate |
-
2011
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3138562A (en) * | 1959-05-23 | 1964-06-23 | Bayer Ag | Cellular polyurethane plastics |
WO2010043624A2 (de) * | 2008-10-15 | 2010-04-22 | Basf Se | Polyesterpolyole auf basis von terephthalsäure |
EP2177555A2 (de) * | 2008-10-16 | 2010-04-21 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyetheresterpolyolen |
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EP2678367B1 (de) | 2014-11-19 |
CN103384689A (zh) | 2013-11-06 |
ES2526791T3 (es) | 2015-01-15 |
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