CN117430773A - 硬质聚氨酯泡沫及其制备方法 - Google Patents
硬质聚氨酯泡沫及其制备方法 Download PDFInfo
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- CN117430773A CN117430773A CN202311260722.6A CN202311260722A CN117430773A CN 117430773 A CN117430773 A CN 117430773A CN 202311260722 A CN202311260722 A CN 202311260722A CN 117430773 A CN117430773 A CN 117430773A
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- China
- Prior art keywords
- strong acid
- lignin
- rigid polyurethane
- polyurethane foam
- polyol
- 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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- 239000002253 acid Substances 0.000 claims abstract description 89
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- 150000003077 polyols Chemical class 0.000 claims abstract description 82
- 239000012948 isocyanate Substances 0.000 claims abstract description 45
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- 238000000034 method Methods 0.000 claims abstract description 16
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Classifications
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- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Abstract
本发明涉及硬质聚氨酯泡沫以及制备所述硬质聚氨酯泡沫的方法,其中所述硬质聚氨酯泡沫是包含强酸木质素、多元醇和异氰酸酯的组合物的聚合产物。本发明通过使用来自生物质的木质素,能够代替部分多元醇且能够制备具有良好物理性质的硬质聚氨酯泡沫,而该木质素无需额外的化学改性。
Description
相关申请
本申请是申请号为201580064036.9、申请日为2015年11月5日、发明名称为“硬质聚氨酯泡沫及其制备方法”的中国发明专利申请的分案申请。
技术领域
本发明涉及硬质聚氨酯泡沫和制备该硬质聚氨酯泡沫的方法。
背景技术
随着可用作为工业原料的化石燃料资源(诸如石油或煤炭)的预期耗尽,越来越多的注意力集中在可永久使用的生物质。在生物质中,木质纤维素生物质是非常有用的,因为没有其他竞争性的使用,例如食物资源的使用。木质纤维素生物质由碳水化合物(诸如纤维素)和木质素组成。木质素是天然酚类聚合物,占木质纤维素生物质的15-20%。
硬质聚氨酯泡沫具有良好的绝缘特性和阻燃特性,因此被广泛应用于冷藏库、冷冻库和其它常规建筑物的绝缘材料以及绝缘板等中。通常,硬质聚氨酯泡沫可以通过在催化剂存在下使多元醇和异氰酸酯反应来制备。
最近,已经尝试使用来自生物质的木质素来制备硬质聚氨酯泡沫。例如,可以使用由亚硫酸盐法制浆工艺中获得的木质素磺酸盐、由苏打法制浆工艺中获得的碱性木质素、来自硫酸盐法造纸过程的硫酸盐(kraft)木质素等等。
然而,这些木质素不易于溶解在多元醇中,或引起过度的交联,因此使硬质聚氨酯泡沫的物理性能恶化。为了解决这些问题,通过化学改性(例如乙酰化或酯化),降低木质素的羟值,以用于制备聚氨酯。因此,需要一种可以通过用木质素代替部分石油基多元醇来制备的硬质聚氨酯泡沫,该木质素无需额外的化学改性。
发明内容
技术问题
本发明提供一种新颖的硬质聚氨酯泡沫和制备该硬质聚氨酯泡沫的方法。
技术方案
根据本发明的一个方面,
提供硬质聚氨酯泡沫以及包含该硬质聚氨酯泡沫的制品,该硬质聚氨酯泡沫是包含强酸木质素、多元醇和异氰酸酯的组合物的聚合产物。
根据本发明的另一个方面,
提供制备硬质聚氨酯泡沫的方法,所述方法包括:在泡沫稳定剂、催化剂和发泡剂的存在下使强酸木质素、多元醇和异氰酸酯反应。
有益效果
本发明通过使用来自生物质的木质素,能够制备具有良好物理性质的硬质聚氨酯泡沫,而该木质素无需额外的化学改性。
具体实施方式
在下文中,将更详细地描述硬质聚氨酯泡沫及其制备方法的示例性实施方式。
根据本发明的一个方面,提供了一种硬质聚氨酯泡沫,其是通过使包含强酸木质素、多元醇和异氰酸酯的组合物进行反应而获得的聚合产物。该硬质聚氨酯泡沫能够被制备成具有优异的性能,而不需要采用常规木质素制备硬质聚氨酯泡沫时所需的额外的化学改性。特别地,与使用其它常规木质素制备的硬质聚氨酯泡沫相比,本发明的硬质聚氨酯泡沫由于使用强酸木质素,因此其制备工艺能够被缩短,且其密度、抗压强度、阻燃性等能够得到改善。
在硬质聚氨酯泡沫中所使用的强酸木质素可以从通过用强酸对木质纤维素生物质进行水解而获得的水解产物中分离。例如,强酸木质素可以使用以下方法制备。首先,木质纤维素生物质可以与强酸混合。随后,可以通过加入过量的水来将所得到的混合物稀释,然后过滤。所得到的残余物可用水洗涤,以得到具有中性pH的残余物。然后将中性残余物干燥,以获得作为干燥粉末的木质素。
例如,作为干燥粉末的强酸木质素可以具有约4至约7的pH。通过使用pH在该范围内的强酸木质素,可以获得具有优异性能的硬质聚氨酯泡沫。当强酸木质素的pH值小于3时,所制备的硬质聚氨酯泡沫在用于保护钢筋时会引起腐蚀。
用于制备强酸木质素的强酸可以是盐酸。然而,实施方式不限于此。例如,强酸可以是不破坏硬质聚氨酯泡沫体的物理性质且在本领域中能够获得的任何强酸,例如可以是硫酸、硝酸、磷酸或路易斯酸。
基于所添加的所述多元醇和所述强酸木质素的混合物的总重量,用于制备硬质聚氨酯泡沫的强酸木质素的含量可以是约1重量%至约40重量%。例如,基于所述多元醇和所述强酸木质素的混合物的总重量,在多元醇和强酸木质素的混合物中强酸木质素的含量可以是约10重量%至约35重量%,并且在一些实施方式中,可以是约10重量%至约30重量%,并且在其他实施方式中,可以是约10重量%至约20重量%。当强酸木质素的含量超过40重量%时,多元醇和强酸木质素的混合物可能具有过度增加的粘度,并且易于硬化,因而难以制备硬质聚氨酯泡沫。
用于制备硬质聚氨酯泡沫的强酸木质素可以具有落入多元醇的羟基范围内的羟值。也就是说,强酸木质素可以具有与用于制备硬质聚氨酯泡沫的多元醇的羟值相同范围内的羟值。由于强酸木质素具有与多元醇的羟值相同的范围内的羟值,可以防止由于使用强酸木质素而导致聚氨酯泡沫的物理性质恶化。
在硬质聚氨酯泡沫中所使用的强酸木质素可以具有约500mg KOH/g或更小的羟值。例如,在硬质聚氨酯泡沫中所使用的强酸木质素可以具有约300mg KOH/g至约500mgKOH/g的羟值。当强酸木质素具有小于300mg KOH/g的羟值时,强酸木质素和多元醇的混合物可能具有过度增加的粘度,或者可能降低硬质聚氨酯泡沫的机械强度。当强酸木质素具有大于500mg KOH/g的羟值时,强酸木质素的分子量分布可能具有大量不可反应的醇,导致聚氨酯的脆性降低。因此,用于与强酸木质素和多元醇的混合物反应所需的异氰酸酯的量可能增加,并且多元醇与异氰酸酯的摩尔比可能超过适当的范围。
例如,使用强酸木质素、多元醇和异氰酸酯制备的硬质聚氨酯泡沫可以具有约25.0kg/m3或更大的密度。例如,硬质聚氨酯泡沫可以具有约25.0kg/m3至约70kg/m3的密度。当硬质聚氨酯泡沫具有小于25.0kg/m3的密度时,硬质聚氨酯泡沫可能具有降低的阻燃性或降低的机械强度。当硬质聚氨酯泡沫具有70kg/m3或更高的密度时,硬质聚氨酯泡沫的成本可能过高。
使用包含强酸木质素、多元醇和异氰酸酯的组合物所制备的硬质聚氨酯泡沫可以具有约0.005kgf/mm2或更大的抗压强度,例如约0.005kgf/mm2至约0.05kgf/mm2。当硬质聚氨酯泡沫具有小于0.005kgf/mm2的抗压强度时,硬质聚氨酯泡沫可能具有降低的阻燃性或降低的机械强度。当硬质聚氨酯泡沫具有大于0.05kgf/mm2的抗压强度时,其成本可能过高。
根据本发明的另一方面,提供了包含根据上述硬质聚氨酯泡沫的制品。该制品可以是聚氨酯发泡成型产品。聚氨酯发泡成型产品可以是汽车部件、机械部件、工业部件、电线、缆线、辊、软管、管、带材、膜材、片材、层压产品、涂料、粘合剂、密封剂、运动用品、休闲用品、鞋类部件、配件、护理用品、住房用品、医疗用品、建筑材料、土木工程相关材料、防水材料、包装材料、隔热材料、冷绝缘材料、搪塑粉等等。硬质聚氨酯泡沫可以在一个表面或其两个相对表面上包含片材。片材可以是例如纸、木材、石膏板、树脂、铝箔或钢板。
根据本发明的另一方面,制备硬质聚氨酯泡沫的方法包括:在泡沫稳定剂、催化剂和发泡剂的存在下使强酸木质素、多元醇和异氰酸酯反应。通过该方法,可以制备硬质聚氨酯泡沫,使得其具有优异的物理性能,例如在密度和抗压强度方面。
在制备方法的一些实施方式中,强酸木质素、多元醇和异氰酸酯的反应可以包括:制备包含强酸木质素、多元醇、泡沫稳定剂、催化剂和发泡剂的预混物;并且使预混物与异氰酸酯反应。
在一些实施方式中,制备方法还可以包括:在制备预混物之前,使强酸木质素与多元醇混合以制备混合物。
在制备方法的一些实施方式中,强酸木质素与多元醇的混合可以在50℃至85℃的温度下进行0.5小时至约2小时。通过在该温度下混合,可以降低多元醇的粘度,这可以促进强酸木质素和多元醇的混合。在强酸木质素和多元醇完全混合后,混合物可以被冷却至约45℃或更低的温度,以抑制其它添加物质的挥发。
在制备方法,强酸木质素的含量可以与如上所述的硬质聚氨酯泡沫的实施方式相同。
在制备方法中使用的多元醇可以是聚醚多元醇、聚酯多元醇、聚烯烃类多元醇、低分子量多元醇、阻燃性多元醇、丙烯酸多元醇或来源于植物的多元醇。然而,实施方法不限于此。可以使用在硬质聚氨酯泡沫的制备中能够使用的在本领域中已知的任何多元醇。
聚醚多元醇的实例包括聚乙二醇、聚丙二醇和聚四亚甲基醚二醇。聚酯多元醇的实例可以包括己二酸酯类多元醇、聚己内酯多元醇、芳族聚酯多元醇和聚碳酸酯二醇。例如,己二酸酯多元醇可以是己二酸乙二醇酯、己二酸二甘醇酯、己二酸丁二醇酯、己二酸三羟甲基丙烷/己二酸二甘醇酯等。聚烯烃多元醇的实例可以包括聚丁二烯多元醇、氢化聚丁二烯多元醇和氢化聚异戊二烯多元醇。低分子量多元醇的实例可以包括1,4-丁二醇、1,6-己二醇、1,3-丙二醇和2-甲基丙烷二醇。阻燃性多元醇的实例可以包括含磷多元醇、含卤素多元醇和酚类多元醇。来自植物的多元醇的实例可以包括来自蓖麻油、大豆油或棕榈油的多元醇。上述多元醇可以单独使用或以其至少两种的组合使用。
多元醇可以具有约400至约8000的分子量。例如,多元醇可以具有约450至约5000的分子量,并且在一些实施方式中,约500至约3000的分子量。当多元醇具有小于400的分子量时,硬质聚氨酯泡沫可能具有降低的柔韧性或降低的耐热性。当多元醇具有大于8000的分子量时,多元醇可能具有降低的与其他多元醇或异氰酸酯的混溶性,使得不能获得均匀的聚氨酯泡沫。
多元醇可以具有约20mgKOH/g至约500mgKOH/g的羟值。每分子多元醇中官能基团的数目可以是2.0至8.0。
在制备方法中,异氰酸酯可以具有约50至约500的异氰酸酯指数。异氰酸酯指数可以由如下等式来定义:
异氰酸酯指数=100x(NCO的用量)/(NCO的理论所需量)
例如,异氰酸酯可以具有约50至约300的异氰酸酯指数,并且在一些实施方式中,约50至约200的异氰酸酯指数。当异氰酸酯指数超过500时,硬质聚氨酯泡沫可能具有增加的脆性和降低的粘附强度。当异氰酸酯指数小于50时,硬质聚氨酯泡沫可能具有降低的阻燃性和降低的抗压强度。
在制备方法中使用的异氰酸酯没有特别限制,只要它是每分子具有至少两个或更多个异氰酸酯基团的多异氰酸酯即可。多异氰酸酯的实例可以是脂族异氰酸酯、脂环族异氰酸酯、芳族异氰酸酯或其改性产物。脂族异氰酸酯的实例可以是六亚甲基二异氰酸酯、赖氨酸二异氰酸酯或赖氨酸三异氰酸酯。例如,脂环族异氰酸酯可以是异佛尔酮二异氰酸酯。芳族异氰酸酯的实例可以是甲苯二异氰酸酯、亚二甲苯基二异氰酸酯、二苯基甲烷二异氰酸酯、聚合的二苯基甲烷二异氰酸酯、三苯甲烷三异氰酸酯或三(异氰酸酯苯基)硫代磷酸酯。改性的异氰酸酯产物的实例可以是氨基甲酸酯预聚物、六亚甲基二异氰酸酯缩二脲、六亚甲基二异氰酸酯三聚体或异佛尔酮二异氰酸酯三聚体。例如,可以使用来自于植物(例如蓖麻油)的异氰酸酯。这些异氰酸酯可以单独使用或以其至少两种的组合使用。
作为氨基甲酸酯化(urethanization)催化剂,可以使用叔胺作为制备方法中使用的催化剂。金属盐和/或季铵盐也可以用作三聚催化剂。在制备方法中,当使用异氰酸酯时,可以组合使用氨基甲酸酯化催化剂和三聚催化剂。例如,可以组合使用叔胺和金属盐和/或季铵盐。
叔胺的实例可以是N,N,N',N'-四甲基乙二胺、N,N,N',N'-四甲基丙二胺、N,N,N',N",N"-五甲基二亚乙基三胺、N,N,N',N",N"-五甲基-(3-氨基丙基)乙二胺、N,N,N',N",N"-五甲基二亚丙基三胺、N,N,N',N'-四甲基胍、1,3,5-三(N,N-二甲基氨基丙基)六氢-s-三嗪、1,8-二氮杂双环[5.4.0]十一碳烯-7,三亚乙基二胺、N,N,N',N'-四甲基六亚甲基二胺、N,N'-二甲基哌嗪、二甲基环己胺、N-甲基吗啉、N-乙基吗啉、双(2-二甲基氨基乙基)醚、1-甲基咪唑、1,2-二甲基咪唑、1-异丁基-2-甲基咪唑、1-二甲基氨基丙基咪唑或N-甲基-N-(N,N-二甲基氨基乙基)乙醇胺。然而,实施方式不限于此。可以使用在本领域中能够获得的任何胺催化剂。
金属盐可以是例如钾盐、锡盐或铅盐。例如,金属盐可以是乙酸钾、2-乙基己酸钾、二月桂酸二丁基锡、辛酸锡、辛酸铅或2-乙基己酸铋。然而,实施方式不限于此。可以使用在本领域中能够获得的任何金属催化剂。
季铵盐可以是例如通过2-乙基己烷与季铵碳酸盐的阴离子交换反应获得的季铵化合物,其中季铵碳酸盐通过使碳酸二酯与如下物质反应获得:四烷基卤化铵,例如四甲基氯化铵;四烷基氢氧化铵,例如四甲基氢氧化铵;四烷基铵有机酸盐,例如四甲基铵2-乙基己酸盐、2-羟丙基三甲基铵甲酸盐或2-羟丙基三甲基铵2-乙基己酸盐;或叔胺,例如N,N,N'N'-四甲基乙二胺。
基于强酸木质素和多元醇的混合物100重量份,催化剂的用量可以是约0.1重量份至约5重量份。然而,实施方式不限于此。催化剂的用量可以在能够制备具有改善的物理性质的硬质聚氨酯泡沫的用量范围内适当地调节。可以根据催化剂的用量,控制强酸木质素和多元醇的混合物与异氰酸酯的反应性。也就是说,可以控制从混合开始到用肉眼确认发泡结束所需的时间。
在制备方法中的发泡剂可以是例如,氢氯氟烃(HCFC)类发泡剂,例如HCFC-141b、HCFC-142b、HCFC-124或HCFC-22;氢氟烃(HFC)类发泡剂,例如1,1,1,2-四氟乙烷(HFC-134a)、1,1,1,3,3-五氟丙烷(HFC-245fa)、1,1,1,3,3-五氟丁烷(HFC-365mfc)、1,1,2,2-四氟乙基二氟甲基醚(HFE-236pc)、1,1,2,2-四氟乙基甲基醚(HFE-254pc)或1,1,1,2,2,3,3-七氟丙基甲基醚(HFE-347mcc);烃发泡剂,例如丁烷、己烷、环己烷、正戊烷、异戊烷或环戊烷等;水;或惰性气体,例如空气、氮气或二氧化碳。然而,实施方式不限于此。可以使用在本领域中能够获得的任何发泡剂。惰性气体可以以液态、超临界状态或亚临界状态加入。除了水以外,上面列出的发泡剂可以单独使用,也可以两种以上的组合使用。
当使用水作为发泡剂时,基于强酸木质素和多元醇的混合物100重量份,水的含量可以是约0.5重量份至约10重量份,例如约0.5重量份至约7重量份。当使用戊烷(正戊烷、异戊烷和/或环戊烷)作为发泡剂时,基于强酸木质素和多元醇的混合物100重量份,戊烷(正戊烷、异戊烷和/或环戊烷)的含量可以是约0.5重量份至约60重量份,例如约0.5重量份至约50重量份。
在制备方法中使用的泡沫稳定剂(表面活性剂)可以是例如,硅基泡沫稳定剂或含氟化合物基泡沫稳定剂。然而,实施方式不限于此。可以使用在本领域中能够获得的任何泡沫稳定剂。例如,可以使用硅基泡沫稳定剂来获得稳定的泡沫。
例如,硅基泡沫稳定剂可以是包含如下的化合物:二甲基聚硅氧烷和聚醚的嵌段共聚物,例如,SZ-1671、SZ-1718、SH-193或SZ-1642(由Dow Corning Toray公司制造);L-6884、L-5440或L-5420(由Momentive公司制造);或者B8443、B8490或B8460(由Evonik制造)。
基于强酸木质素和多元醇的混合物100重量份,泡沫稳定剂的含量可以是约0.1重量份至约10重量份。例如,基于强酸木质素和多元醇的混合物100重量份,泡沫稳定剂的含量可以是约0.3重量份至约5重量份。
在一些实施方式中,在制备方法中,可以选择性地使用阻燃剂。
阻燃剂的实例可以是磷酸酯,例如磷酸三乙酯、磷酸三丁酯、磷酸三氯乙酯、磷酸三氯丙酯(TCPP)、磷酸三苯酯、磷酸三甲苯酯或多磷酸;磷酸化合物如亚磷酸酯;或氯化石蜡。
为了在所制得的硬质泡沫中同时确保改进的机械性能和改进的阻燃性,基于强酸木质素和多元醇的混合物100重量份,阻燃剂的用量可以为约10重量份至约60重量份。例如,基于强酸木质素和多元醇的混合物100重量份,阻燃剂的含量可以为约20重量份至约40重量份。
在一些实施方式中,在制备方法中,还可以使用另外的配合剂。
除了上文所描述的强酸木质素、多元醇、异氰酸酯、催化剂、发泡剂和泡沫稳定剂之外,还可以使用任何配合剂。配合剂的实例可以是填充剂,例如碳酸钙或硫酸钡;抗老化剂,例如抗氧化剂或紫外(UV)光吸收剂;增塑剂;着色剂;抗真菌剂;消泡剂;分散剂;或者防变色剂。
实施例
现在将参考以下实施例和比较例详细地描述本发明的一个或多个实施方式。然而,这些实施例仅仅是为了说明的目的,并不意图限制本发明的一个或多个实施方式的范围。
(硬质聚氨酯泡沫的制备)
实施例1:来自松木的强酸木质素
(强酸木质素的制备)
使用松木作为木质纤维素生物质。将松木粉碎至约0.8mm或更小的直径之后,将作为原料的经粉碎的松树与42%的盐酸以约1:5(w/v)的重量比混合并在约20℃下搅拌约5小时,并向混合物中加入过量的水以稀释盐酸。随后,对稀释的溶液,通过不锈钢筛(325-ASTM)过滤残留物。用水将过滤所得残留物洗涤至4或更大的pH,然后在70℃烘箱中干燥,以得到盐酸-木质素(hydrochloric acid-hydrolytic lignin)。盐酸-木质素的糖含量小于5重量%,并且氯含量为约1重量%或更小。
(预混物的制备)
将10g制备的强酸木质素和90g市售液体多元醇(3422,聚丙二醇,Mw=600,可得自BASF)加入到反应器中并以约300rpm在约85℃下搅拌约1小时,以制备强酸木质素和多元醇的混合物。将混合物的温度冷却至约45℃。将1.5g硅泡沫稳定剂(B-8409,由Evonik Industries制造)、2.0g作为主催化剂的胺催化剂(33-LV,由Air Products and Chemicals,Inc.制造),0.3g作为辅助催化剂的锡催化剂(DBTDL,二月桂酸二丁基锡,由Sigma制造)和100g混合物混合后,添加28.5g作为发泡剂的正戊烷,以制备预混物。每个实施例中的预混物的组成示于表1中。
(硬质聚氨酯泡沫的制备)
通过将119g异氰酸酯(聚合MDI(二苯基甲烷二异氰酸酯),Suprasec 5005,由NISCHEM制造)加入到预混物中来制备硬质聚氨酯泡沫。异氰酸酯的添加量根据预混物中的羟基的添加量和发泡剂的添加量来确定,以使异氰酸酯指数为约100。
将预混物和异氰酸酯快速放入室温下的聚乙烯容器中,并以约3000rpm搅拌约3秒钟以在1升容器内引起发泡,从而得到硬质聚氨酯泡沫。
实施例2~10
以与实施例1相同的方式制备硬质聚氨酯泡沫,不同之处在于硬质聚氨酯泡沫体的组成改变。硬质聚氨酯泡沫的组成如表1所示。
比较例1
以与实施例1相同的方式制备硬质聚氨酯泡沫,不同之处在于不使用强酸木质素,并使用100g市售的液态多元醇。
比较例2
以与实施例1相同的方式制备硬质聚氨酯泡沫,不同之处在于将强酸木质素的含量改变为50g。
【表1】
实例 | 市售的多元醇 | 木质素 | 泡沫稳定剂 | 催化剂 | 发泡剂 | 异氰酸酯 |
实施例1 | 90 | 10 | 1.5 | 2.3 | 28.5 | 119 |
实施例2 | 90 | 10 | 1.5 | 2.3 | 47.0 | 119 |
实施例3 | 90 | 10 | 1.5 | 2.3 | 1.0(水) | 134 |
实施例4 | 80 | 20 | 1.5 | 2.3 | 28.5 | 115 |
实施例5 | 70 | 30 | 1.5 | 2.3 | 28.5 | 112 |
实施例6 | 70 | 30 | 1.5 | 2.3 | 47.0 | 112 |
实施例7 | 70 | 30 | 1.5 | 2.3 | 1.0(水) | 127 |
实施例8 | 60 | 40 | 1.5 | 2.3 | 28.5 | 108 |
实施例9 | 60 | 40 | 1.5 | 2.3 | 47.0 | 108 |
实施例10 | 60 | 40 | 1.5 | 2.3 | 1.0(水) | 124 |
比较例1 | 100 | 0 | 1.5 | 2.3 | 28.5 | 122 |
比较例2 | 50 | 50 | 1.5 | 2.3 | 28.5 | 105 |
在表1中,各组分的量以克(g)为单位表示。在实施例3、7和10中,作为发泡剂,使用水代替正戊烷。
评价例1:羟值计算
通过测试方法(ASTM D-4274-99)测定强酸木质素中羟基的含量。羟值被定义为用于中和从1g多元醇所获得的乙酰化化合物中的乙酸所需的氢氧化钾的重量(mgKOH/g)。
向0.2g强酸木质素和空白样品二者中均加入10mL吡啶和1.3mL乙酸酐,然后在98±2℃水浴中反应约2小时,然后冷却至室温。在每个反应溶液中加入30mL去离子水后,将反应溶液转移到锥形管中,并将去离子水进一步加入到每个锥形管中至约45.5mL的体积。从每种反应溶液中收集上清液。进一步向每个锥形管中的沉淀物中加入40mL蒸馏水,然后进行离心分离并进一步收集上清液。将上清液加入到先前收集的上清液中。向收集的上清液中加入1mL的1%酚酞溶液,并在搅拌的同时用0.5N NaOH溶液滴定,直到溶液的颜色变成淡粉红色。此时,测量所加入的NaOH的量。使用等式2从NaOH的加入量计算羟值。
<等式2>
羟值(mgKOH/g)=[(加入到空白样中的NaOH溶液的量(mL)–加入到木质素中的NaOH溶液的量(mL))×NaOH溶液的浓度(N)×56.1]/所加入的木质素的量(g)
实施例1的来自松木的强酸木质素的羟值为约350mgKOH/g,实施例13的来自金合欢的强酸木质素的羟值为约419mgKOH/g。用于制备硬质聚氨酯泡沫的市售多元醇的羟值为约350-560mgKOH/g,并且强酸木质素的羟值在市售多元醇的羟值范围内。
评价例2:反应性
测量乳化时间和凝胶时间,其中,乳化时间是从预混物和异氰酸酯的混合的起始时间(设定为0(秒))到在每个源发泡组合物中开始发泡所需的时间,并且其中凝胶时间是从每个源发泡组合物中开始发泡直到硬质泡沫停止上升所需的时间。测定结果如表2中所示。乳化时间和凝胶时间越短,反应性越优异。
评价例3:密度(cupfree density(无杯密度))的测量
将每个硬质聚氨酯泡沫的核心区域切成尺寸为70mm(长)×70mm(宽)×70mm(厚度)的立方体,其密度(kg/m3)由其重量和体积计算得到。结果示于表2中。
评价例4:抗压强度测量
使用JIS K-6400测试方法测量相对于原始厚度被压缩25%时的每个硬质聚氨酯泡沫的抗压强度。结果示于表2中。
【表2】
参考表2,与不含木质素的比较例1的硬质聚氨酯泡沫相比,实施例的硬质聚氨酯泡沫具有相似的物理性能和改进的反应性。
在比较例2中,由于预混物的粘度增加,硬质聚氨酯泡沫未能适当地形成。
因此,应当理解,硬质聚氨酯泡沫可以仅通过用强酸性木质素取代部分多元醇来制备,而不需要对强酸木质素进行额外的化学改性。
工业实用性
本发明通过使用从生物质获得的木质素,能够制备具有优异的物理性质的硬质聚氨酯泡沫,而不需要对木质素进行额外的化学改性。
Claims (10)
1.一种硬质聚氨酯泡沫,所述硬质聚氨酯泡沫是包含具有4至7的pH的强酸木质素的粉末、具有20至500mg KOH/g的羟值的多元醇和异氰酸酯的组合物的聚合产物,
其中,基于所述多元醇和所述强酸木质素的粉末的混合物的总重量,所述强酸木质素的粉末的含量是10重量%至40重量%,并且
其中,所述强酸木质素是从通过用强酸对木质纤维素生物质进行水解而获得的水解产物中分离得到的木质素,并且所述强酸木质素的糖含量小于5重量%。
2.根据权利要求1所述的硬质聚氨酯泡沫,其中所述强酸选自由盐酸、硫酸、硝酸和路易斯酸构成的组。
3.根据权利要求1所述的硬质聚氨酯泡沫,其中基于所述多元醇和所述强酸木质素的混合物的总重量,所述强酸木质素的含量是10重量%至30重量%。
4.根据权利要求1所述的硬质聚氨酯泡沫,其中所述强酸木质素的羟值在所述多元醇的羟值范围内。
5.根据权利要求1所述的硬质聚氨酯泡沫,其中所述强酸木质素的羟值是300mg KOH/g至500mg KOH/g。
6.一种包含根据权利要求1至5中任意一项所述的硬质聚氨酯泡沫的制品。
7.一种制备硬质聚氨酯泡沫的方法,所述方法包括:在泡沫稳定剂、催化剂和发泡剂的存在下使具有4至7的pH的强酸木质素的粉末、具有20至500mgKOH/g的羟值的多元醇和异氰酸酯反应,
其中,基于所述多元醇和所述强酸木质素的混合物的总重量,所述强酸木质素的含量是10重量%至40重量%,并且
其中,所述强酸木质素是从通过用强酸对木质纤维素生物质进行水解而获得的水解产物中分离得到的木质素,并且所述强酸木质素的糖含量小于5重量%。
8.根据权利要求7所述的制备硬质聚氨酯泡沫的方法,其中强酸木质素、多元醇和异氰酸酯的反应包括:
制备包含所述强酸木质素、所述多元醇、所述泡沫稳定剂、所述催化剂和所述发泡剂的预混物;并且
使所述预混物与所述异氰酸酯反应。
9.根据权利要求7所述的制备硬质聚氨酯泡沫的方法,还包括:在制备所述预混物之前,使所述强酸木质素与所述多元醇混合以制备混合物。
10.根据权利要求9所述的制备硬质聚氨酯泡沫的方法,其中所述强酸木质素与所述多元醇的混合在50℃至85℃的温度下进行0.5小时至2小时。
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CN101362818B (zh) * | 2008-09-12 | 2012-01-11 | 南昌大学 | 一种竹废料液化产物制备生物可降解聚氨酯硬质泡沫的方法 |
US8409403B2 (en) | 2009-10-23 | 2013-04-02 | David H. Blount | Production of amino lignin and amino lignin cellulose resins and adhesives |
JP2011184643A (ja) | 2010-03-11 | 2011-09-22 | Kawasaki Kasei Chem Ltd | ポリエステルポリオール及び硬質ポリウレタンフォームの製造方法 |
EP2847202B1 (en) * | 2012-05-03 | 2019-04-17 | Virdia, Inc. | Methods for treating lignocellulosic materials |
EP2677030A1 (en) * | 2012-06-21 | 2013-12-25 | Latvijas Valsts Koksnes kimijas instituts | Polyurethane rigid and flexible foams as composite obtained from wood origin raw materials and used as support for immobilization of microorganisms that produce ligninolytic enzymes |
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CN103275332B (zh) * | 2013-06-06 | 2016-02-03 | 济南圣泉集团股份有限公司 | 一种玉米芯木质素及应用 |
CN103665300A (zh) | 2013-12-05 | 2014-03-26 | 天津工业大学 | 一种制备木质素型聚氨酯泡沫材料的方法 |
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2014
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2015
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- 2015-11-05 US US15/529,040 patent/US10604615B2/en active Active
- 2015-11-05 BR BR112017010915-8A patent/BR112017010915B1/pt active IP Right Grant
- 2015-11-05 DK DK15863623.3T patent/DK3225661T3/da active
- 2015-11-05 HU HUE15863623A patent/HUE055822T2/hu unknown
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- 2015-11-05 WO PCT/KR2015/011828 patent/WO2016085145A1/ko active Application Filing
- 2015-11-05 MY MYPI2017000760A patent/MY178096A/en unknown
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- 2015-11-05 CN CN202311260722.6A patent/CN117430773A/zh active Pending
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MY178096A (en) | 2020-10-02 |
BR112017010915A2 (pt) | 2018-02-06 |
EP3225661B1 (en) | 2021-05-12 |
HUE055822T2 (hu) | 2021-12-28 |
JP6559782B2 (ja) | 2019-08-14 |
KR20160062559A (ko) | 2016-06-02 |
EP3225661A4 (en) | 2018-08-08 |
WO2016085145A1 (ko) | 2016-06-02 |
JP2017537194A (ja) | 2017-12-14 |
ES2879334T3 (es) | 2021-11-22 |
CN107001565A (zh) | 2017-08-01 |
EP3225661A1 (en) | 2017-10-04 |
US10604615B2 (en) | 2020-03-31 |
US20170253689A1 (en) | 2017-09-07 |
BR112017010915B1 (pt) | 2021-11-16 |
PL3225661T3 (pl) | 2021-11-15 |
DK3225661T3 (en) | 2021-05-25 |
JP2019143150A (ja) | 2019-08-29 |
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