CN114341224A - 减少聚酯多元醇和聚氨酯泡沫中醛排放的方法 - Google Patents
减少聚酯多元醇和聚氨酯泡沫中醛排放的方法 Download PDFInfo
- Publication number
- CN114341224A CN114341224A CN201980099727.0A CN201980099727A CN114341224A CN 114341224 A CN114341224 A CN 114341224A CN 201980099727 A CN201980099727 A CN 201980099727A CN 114341224 A CN114341224 A CN 114341224A
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- China
- Prior art keywords
- hydrogen
- oxopropanamide
- compound
- hydroxyalkyl
- isocyanate
- 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.)
- Pending
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- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/125—Water, e.g. hydrated salts
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/285—Nitrogen containing compounds
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
聚氨酯泡沫通过固化含有以下的反应混合物制备:芳香族多异氰酸酯、至少一种平均官能度为至少2并且每个异氰酸酯反应性基团的当量为至少200的异氰酸酯反应性材料、至少一种发泡剂、至少一种表面活性剂和至少一种催化剂,以及某些3‑氧代丙酰胺化合物。由此生产的泡沫排放低水平的醛。
Description
本发明涉及表现出低水平的醛的聚酯多元醇,并且涉及用于生产这类聚氨酯的方法。
聚氨酯泡沫用于许多办公室、家庭和车辆应用中。它们例如用于电器应用中并且用作床上用品和家具的缓冲。在汽车和卡车中,聚氨酯被用作座椅缓冲,用于头枕、仪表板和仪器面板、扶手、车顶内衬、噪音、振动和刺耳的消减措施,用作声学消减措施和其他应用。
这些聚氨酯经常排放不同水平的醛,如甲醛、乙醛和丙醛。由于这些泡沫的泡孔结构,泡沫中含有的醛容易逸出到大气中。这可存在气味问题和暴露问题,尤其是当人或动物暴露于封闭空间内的材料时。车辆制造商对用于汽车、卡车、公交车、火车和飞机的客舱的材料的排放施加更严格的限制。
清除剂有时用于减少各种类型的材料的醛排放。在聚氨酯领域,有例如WO 2006/111492,其描述将抗氧化剂和受阻胺光稳定剂(HALS)加到多元醇以减少醛。WO 2009/114329描述用某些类型的氨基醇处理多元醇和用某些硝基烷烃处理多异氰酸酯,以便分别减少在多元醇和多异氰酸酯中,以及在由这些材料制造的聚氨酯中的醛。JP 2005-154599描述出于所述目的向聚氨酯制剂中添加碱金属硼氢化物。美国专利号5,506,329描述某些醛亚胺噁唑烷化合物用于从含多异氰酸酯的制剂中清除甲醛的用途,并且描述硝基烷烃和氨基醇作为在纺织物和胶合板应用中的甲醛清除剂。
这些方法提供有限的益处,部分是因为存在于聚氨酯泡沫中的醛不总是从用于制造泡沫的原材料中携带进来。具体地说,甲醛和乙醛可在固化步骤期间或当泡沫随后经受UV光、高温或其它条件时形成。
WO 2018/148898描述将氨基醇与某些抗氧化剂一起用于减少来自聚氨酯泡沫的醛排放。此组合提供一些改进,但是需要更大程度地减少醛排放。
在美国专利号10,196,493和美国公开专利申请号2019-0119460中,某些乙酰乙酰胺化合物被描述为聚氨酯泡沫的醛清除剂。
因此,需要一种有效并且经济地减少醛排放的方法。优选地,此方法不导致聚氨酯的特性或性能的显著改变。
本发明为一种用于生产聚氨酯泡沫的方法,所述方法包括形成含有以下的反应混合物:芳香族多异氰酸酯、至少一种平均官能度为至少2并且每摩尔异氰酸酯反应性基团的当量为至少200克的异氰酸酯反应性材料、至少一种发泡剂、至少一种表面活性剂和至少一种催化剂;和在至少一种3-氧代丙酰胺化合物的存在下固化反应混合物以形成聚氨酯泡沫的方法,其中所述3-氧代丙酰胺化合物是通过结构I表示的化合物:
其中R1为氢或烃基,R2为氢、烃、羟烷基或氨基烷基,R3为羟烷基或氨基烷基,并且n为至少1。
本发明还为一种用于减少聚氨酯泡沫的醛排放的方法,所述方法包括:a)将至少一种3-氧代丙酰胺化合物与至少一种平均官能度为至少2并且每摩尔异氰酸酯反应性基团的当量为至少200克的异氰酸酯反应性材料组合以形成混合物,并且然后b)将来自步骤a)的混合物与至少一种有机多异氰酸酯组合,并且在至少一种发泡剂、至少一种表面活性剂和至少一种催化剂存在下固化所得反应混合物以形成聚氨酯泡沫,其中3-氧代丙酰胺化合物为通过结构I表示的化合物,其中R1为氢或烃基,R2为氢、烃、羟烷基或氨基烷基,R3为氢、羟烷基或氨基烷基,并且n为至少1。
本发明还为一种以上述方法中的任一种制造的聚氨酯泡沫。
本发明还是一种降低聚醚多元醇的醛排放的方法,所述方法包括将0.01-5重量份的至少一种3-氧代丙酰胺化合物与100重量份的聚醚多元醇组合,其中3-氧代丙酰胺化合物是由结构I表示的化合物,其中R1为氢或未取代或惰性取代的烃基,R2为氢、烃、羟烷基或氨基烷基,R3为氢、羟烷基或氨基烷基,并且n为至少1。
本发明还涉及一种羟基当量为至少200克/当量羟基的聚醚多元醇,其每100重量份的聚醚多元醇中含有0.01-5重量份的至少一种3-氧代丙酰胺化合物,其中3-氧代丙酰胺化合物是由结构I表示的化合物,其中R1为氢或未取代或惰性取代的烃基,R2为氢、烃、羟烷基或氨基烷基,R3为氢、羟烷基或氨基烷基,并且n为至少1。
已经发现结构I的3-氧代丙酰胺化合物的存在降低聚氨酯泡沫和聚醚多元醇释放的醛的水平。3-氧代丙酰胺化合物具有对异氰酸酯基团具有反应性的进一步优点。因此,它在固化步骤期间发生反应,从而结合到聚氨酯聚合物结构中。这进一步减少有机化合物的排放。此外,结构I的3-氧代丙酰胺化合物耐水解,这减少挥发性水解副产物的产生和潜在排放。3-氧代丙酰胺化合物不会增加聚醚多元醇或泡沫中的总挥发性有机化合物。
在结构I中,R1是氢或烃基。如果是烃基,R1可以是芳族、脂族、脂环族或其任何组合。R1优选具有至多50个碳原子,更优选至多10个碳原子,至多6个碳原子或至多4个碳原子。
在具体实施方案中,R1可以是烷基,例如甲基、乙基、丙基、丁基、戊基、己基等(包括任何前述的任何异构体;环己基;烷基取代的环己基;苯基和烷基取代的苯基,在每种情况优选具有至多10个,特别是至多6个碳原子。
在一些实施方案中,R2是氢或具有至多6、优选2至4个碳原子的氨基烷基或羟烷基。R2最优选地为氢。
R3优选为具有至多6个,尤其是2至4个碳原子的羟烷基。R3最优选为2-羟乙基(-CH2-CH2-OH)或2-羟丙基(-CH2-CH(CH3)-OH)。
n优选为1至6,更优选为1至4。在具体实施方案中,n可以是1、2、3或4。n最优选为1。
在一些实施方案中,R1是苯基或具有至多6个碳原子的烷基,R2是氢,R3是2-羟乙基或2-羟丙基并且n是1。特别优选的3-氧代丙酰胺是N-(2-羟乙基)-3-氧代丁酰胺,其对应于结构I,其中R1是甲基,R2是氢,R3是2-羟乙基并且n是1。
为了生产根据本发明的泡沫,使至少一种多异氰酸酯与至少一种官能度为至少2并且每摩尔异氰酸酯反应性基团的当量为至少200克的异氰酸酯反应性化合物反应。如下所述,可存在其它成分。该反应在结构I的3-氧代丙酰胺化合物存在下进行。
3-氧代丙酰胺化合物的合适量为0.01至5pph(即,每100重量份的一种或多种每分子具有至少两个异氰酸酯反应性基团并且每个异氰酸酯反应性基团的当量为至少200的异氰酸酯反应性化合物0.01至5重量份)。优选的最小量为至少0.1或至少0.2pph,并且优选的最大量为至多2.5、至多1.5、至多1、至多0.75或至多0.5pph。
结构I的3-氧代丙酰胺化合物可以与用于生产泡沫的制剂中各种成分中的任一种或多种的混合物形式提供。可替代地,可将它作为单独的组分或流加到反应中,而无需事先与其它成分中的任一种组合。
然而,优选地,将3-氧代丙酰胺化合物与一种或多种每分子具有至少两个异氰酸酯反应性基团并且每摩尔异氰酸酯反应性基团的当量为至少200克的异氰酸酯反应性化合物共混,然后形成聚氨酯泡沫。异氰酸酯反应性化合物优选包括至少一种聚醚多元醇。将所得共混物在大约室温或更高温度下(但低于3-氧代丙酰胺化合物的沸腾温度,并且低于多元醇降解的温度)维持至少30分钟的时段,然后制备泡沫。这类共混物可在这类条件下维持任何任意更长的时间,如至多一个月、至多一周或至多一天。
泡沫制剂包括至少一种官能度为至少2并且每摩尔异氰酸酯反应性基团的当量为至少200克的异氰酸酯反应性化合物。“官能度”是指每分子异氰酸酯反应性基团的平均数。官能度可高达8或更多,但是优选地为2至4。异氰酸酯基团可为例如羟基、伯氨基和/或仲氨基,但是羟基是优选的。当量可为至多6000或更大,但是优选地为500至3000,并且更优选地为1000至2000。此异氰酸酯反应性化合物可为例如聚醚多元醇、聚酯多元醇、羟基终止的丁二烯聚合物或共聚物、含有羟基的丙烯酸酯聚合物等。优选类型的异氰酸酯反应性化合物为聚醚多元醇,尤其是环氧丙烷的聚合物或环氧丙烷和环氧乙烷的共聚物。环氧丙烷和环氧乙烷的共聚物可为具有末端聚(氧化乙烯)嵌段并且其中至少50%的羟基为伯羟基的嵌段共聚物。另一种合适的环氧丙烷和环氧乙烷的共聚物可为无规或伪无规共聚物,其还可含有末端聚(氧化乙烯)嵌段并且其中至少50%的羟基为伯羟基。
用作异氰酸酯反应性化合物的聚酯多元醇包括多元醇,优选地二醇与多元羧酸或其酸酐,优选地二羧酸或二羧酸酐的反应产物。多元羧酸或酸酐可为脂肪族、环脂肪族、芳香族和/或杂环的并且可为如被卤素原子取代的。多元羧酸可为不饱和的。这些多元羧酸的实例包括丁二酸、己二酸、对苯二甲酸、间苯二甲酸、偏苯三酸酐、邻苯二甲酸酐、顺丁烯二酸、顺丁烯二酸酐和反丁烯二酸。用于制造聚酯多元醇的多元醇的当量可为约150或更小,并且包括乙二醇、1,2-和1,3-丙二醇、1,4-和1,3-丁二醇、1,6-己二醇、1,8-辛二醇、新戊二醇、环己烷二甲醇、2-甲基-1,3-丙二醇、丙三醇、三羟甲基丙烷、1,2,6-己三醇、1,2,4-丁三醇、三羟甲基乙烷、季戊四醇、对环己二醇、甘露醇、山梨糖醇、甲基糖苷、二乙二醇、三乙二醇、四乙二醇、二丙二醇、二丁二醇等。聚己内酯多元醇,如以商品名“Tone”由陶氏化学公司出售的那些也为有用的。
如果需要,那么可使用官能度为至少2并且每摩尔异氰酸酯反应性基团的当量为至少200克的前述异氰酸酯反应性化合物中的两种或更多种的混合物。
一种或多种异氰酸酯反应性化合物可含有分散的聚合物颗粒。这些所谓的聚合物多元醇例如含有乙烯基聚合物的颗粒,如苯乙烯、丙烯腈或苯乙烯-丙烯腈、聚脲聚合物的颗粒,或聚氨酯-脲聚合物的聚合物,在每种情况下都分散在连续多元醇相中。
此外,前述异氰酸酯反应性化合物可与一种或多种交联剂和/或增链剂掺合使用。出于本说明书的目的,“交联剂”为每分子具有至少三个异氰酸酯反应性基团并且每摩尔异氰酸酯基团的当量低于200克的化合物。出于本发明的目的,“增链剂”每分子恰好具有两个异氰酸酯反应性基团并且每摩尔异氰酸酯反应性基团的当量低于200克。在每种情况下,异氰酸酯反应性基团优选地为羟基、伯氨基或仲氨基。交联剂和增链剂的当量优选地为至多150,并且更优选地至多约125。
交联剂的实例包括丙三醇、三羟甲基丙烷、三羟甲基乙烷、二乙醇胺、三乙醇胺、三异丙醇胺、任何前述的当量为至多199的烷氧基化物等。增链剂的实例包括亚烷基二醇(例如,乙二醇、丙二醇、1,4-丁二醇、1,6-己二醇等)、二醇醚(如二乙二醇、三乙二醇、二丙二醇、三丙二醇等)、乙二胺、甲苯二胺、二乙基甲苯二胺等,以及任何前述的当量为至多199的烷氧基化物等。
交联剂和/或增链剂典型地以少量存在(如果有的话)。优选的量为0至5pph的交联剂和/或增链剂。更优选的量为0.05至2pph,并且再更优选的量为0.1至1pph的一种或多种交联剂。
合适的多异氰酸酯的实例包括例如,间苯二异氰酸酯、2,4-和/或2,6-甲苯二异氰酸酯(TDI)、二苯基甲烷二异氰酸酯(MDI)的各种异构体、所谓的聚合MDI产品(其为多亚甲基多亚苯基多异氰酸酯在单体MDI中的混合物)、碳化二亚胺改性的MDI产品(如所谓的“液体MDI”产品,其异氰酸酯当量在135-170的范围内)、六亚甲基-1,6-二异氰酸酯、四亚甲基-1,4-二异氰酸酯、环己烷-1,4-二异氰酸酯、六氢甲苯二异氰酸酯、氢化MDI(H12MDI)、异佛尔酮二异氰酸酯、亚萘基-1,5-二异氰酸酯、甲氧基苯基-2,4-二异氰酸酯、4,4'-亚联苯基二异氰酸酯、3,3'-二甲氧基-4,4'-联苯基二异氰酸酯、3,3'-二甲基二苯基甲烷-4,4'-二异氰酸酯、4,4',4”-三苯基甲烷二异氰酸酯、氢化多亚甲基多苯基多异氰酸酯、甲苯-2,4,6-三异氰酸酯和4,4'-二甲基二苯基甲烷-2,2',5,5’-四异氰酸酯。可使用改性以含有氨基甲酸酯、脲、脲并亚胺、缩二脲、脲基甲酸酯和/或碳化二亚胺基的任何前述物质。
优选的异氰酸酯包括TDI、MDI和/或聚合MDI,以及含有氨基甲酸酯、脲、脲并亚胺、缩二脲、脲基甲酸酯和/或碳二亚胺基团的MDI和/或聚合MDI的衍生物。尤其优选的异氰酸酯为TDI和MDI的混合物。
提供给泡沫制剂的多异氰酸酯的量表示为“异氰酸酯指数”,其为泡沫制剂中异氰酸酯基团与异氰酸酯反应性基团的比率的100倍。异氰酸酯指数典型地为约60至150。优选的异氰酸酯指数为60至125,并且更优选的异氰酸酯指数为65至115。在一些实施方案中,异氰酸酯指数为70至115或75至115。
发泡剂可为化学(放热)类型、物理(吸热)类型或每种类型中的至少一种的混合物。化学类型典型地在发泡反应的条件下反应或分解以产生二氧化碳或氮气。水和各种氨基甲酸酯化合物为合适的化学发泡剂的实例。物理类型包括二氧化碳、各种低沸点烃、氢氟烃、氢氟氯烃、醚等。水为最优选的发泡剂,其自身或与一种或多种物理发泡剂组合。
发泡剂以足以提供期望泡沫密度的量存在。当水为发泡剂时,合适的量大体上为1.5至6pph,优选地2至5pph。
合适的表面活性剂为有助于发泡反应混合物的泡孔稳定直到材料已固化的材料。如通常在制造聚氨酯泡沫中使用的各种硅酮表面活性剂可用于用本发明的聚合物多元醇或分散体制造泡沫。这类硅酮表面活性剂的实例为以商品名称TegostabTM(赢创公司(Evonik Corporation))、NiaxTM(迈图(Momentive))和DabcoTM(空气化工产品公司)可商购的。
表面活性剂典型地以至多5pph,更典型地0.1至2pph,并且优选地0.25至1.5pph的量存在。
合适的催化剂包括由美国专利号4,390,645所述的那些,所述专利以引用的方式并入本文中。代表性催化剂包括:
(a)叔胺,如三甲胺、三乙胺、N-甲基吗啉、N-乙基吗啉、N,N-二甲基苯甲胺、N,N-二甲基乙醇胺、N,N,N',N'-四甲基-1,4-丁二胺、N,N-二甲基哌嗪、1,4-二氮杂双环-2,2,2-辛烷、双(二甲基氨基乙基)醚、双(2-二甲基氨基乙基)醚、吗啉、4,4'-(氧代-2,1-乙烷二基)双,三(二甲基氨基丙基)胺、五甲基二亚乙基三胺和三亚乙基二胺等;以及含有一个或多个异氰酸酯反应性基团的所谓“低发射(low emissive)”叔胺催化剂,如二甲基胺丙胺等;
(b)叔膦,如三烷基膦和二烷基苯甲基膦;
(c)各种金属的螯合物,如可从乙酰丙酮、苯甲酰丙酮、三氟乙酰丙酮、乙酰乙酸乙酯等与金属如Be、Mg、Zn、Cd、Pd、Ti、Zr、Sn、As、Bi、Cr、Mo、Mn、Fe、Co和Ni获得的那些;
(d)强酸的酸性金属盐,如氯化铁、氯化锡、氯化亚锡、三氯化锑、硝酸铋和氯化铋;
(e)强碱,如碱金属和碱土金属氢氧化物、烷氧化物和苯氧化物;
(f)各种金属的醇化物和酚化物,如Ti(OR)4、Sn(OR)4和Al(OR)3,其中R为烷基或芳基,和醇化物与羧酸、β-二酮和2-(N,N-二烷基氨基)醇的反应产物;
(g)有机酸与各种金属,如碱金属、碱土金属、Al、Sn、Pb、Mn、Co、Ni和Cu的盐,包括例如乙酸钠、辛酸亚锡、油酸亚锡、辛酸铅、金属干燥剂,如环烷酸锰和环烷酸钴;和
(h)四价锡、三价和五价As、Sb和Bi的有机金属衍生物以及铁和钴的羰基金属。
催化剂典型地以少量存在,如至多2pph并且大体上至多1pph。催化剂的优选的量为0.05至1pph。
可以在存在减少所得泡沫中的醛和/或其他排放物的附加化合物的情况下生产泡沫。其中有氨基醇化合物,其特征在于具有至少一个伯氨基或仲氨基和至少一个羟基,每个都与一个脂肪族碳原子键合,还有烷基羟胺化合物,其包括-NH-OH基团,其中氮原子与脂肪族碳原子键合。
氨基醇化合物为已知的并且包括例如在美国公开号2009/0227758和2010/0124524中描述的那些,所述公开中的每一个都以其全文并入本文中。
在一些实施方案中,氨基醇或烷基羟胺化合物为由结构II表示的化合物:
或这类化合物的盐,其中
R6、R7和R8各自独立地为H、任选地被苯基或NR9R10取代的烷基,其中R9和R10独立地为H、C1-C6烷基、苯基或任选地独立地被苯基或NR9R10取代的羟烷基;
R5为H、羟基、苯基、任选地被苯基或NR9R10取代的烷基或任选地独立地被苯基或NR9R10取代的羟烷基,其条件是当R6、R7和R8中没有一个为羟烷基时,则R5为任选地独立地被苯基或NR9R10取代的羟基或羟烷基。
合适的氨基醇的具体实例为2-氨基-1-丁醇、2-氨基-2-乙基-1,3-丙二醇、2-氨基-2-甲基-1-丙醇、2-氨基-1-甲基-1,3-丙二醇、1,1,1-三(羟甲基)甲胺、乙醇胺、二乙醇胺、N-甲基乙醇胺、N-丁基乙醇胺、单异丙醇胺、2-氨基-2(羟甲基)丙烷-1,3-二醇、二异丙醇胺、单仲丁醇胺、二仲丁醇胺或其盐。这些氨基醇可购自各种商业来源,包括安格斯化学公司(美国伊利诺伊州布法罗格罗夫)(ANGUS Chemical Company(Buffalo Grove,Ill.,USA))、陶氏化学公司(美国密歇根州米德兰)(The Dow Chemical Company(Midland,Mich.,USA)),或可通过在本领域中众所周知的技术容易制备。氨基醇可以盐的形式使用。合适的盐包括盐酸盐、乙酸盐、甲酸盐、草酸盐、柠檬酸盐、碳酸盐、硫酸盐和磷酸盐。
烷基羟胺的具体实例包括N-异丙基羟胺、N-乙基羟胺、N-甲基羟胺、N-(正丁基)羟胺、N-(仲丁基)羟胺等。
可以在至少一种抗氧化剂的存在下生产泡沫。合适的抗氧化剂的实例包括酚类化合物、胺类抗氧化剂、硫代增效剂如硫代二丙酸二月桂酯或硫代二丙酸二硬脂酯、亚磷酸酯和亚膦酸酯、苯并呋喃酮和二氢吲哚酮,如美国专利号4,325,863、美国专利号4,338,244、美国专利号5,175,312、美国专利号5,216,052、美国专利号5,252,643、DE-A-4316611、DE-A-4316622、DE-A-4316876、EP-A-0589839或EP-A-0591102中公开的那些;生育酚、羟基化的硫代二苯醚、O-、N-和S-苄基化合物、羟基苄基丙二酸酯、三嗪化合物、苄基膦酸酯、酰基氨基酚、β-(3,5-二叔丁基-4-羟基苯基)丙酸的酰胺、抗坏血酸(维生素C)、2-(2'-羟基苯基)苯并三唑、2-羟基二苯甲酮、取代和未取代的苯甲酸酯、丙烯酸酯、镍化合物、草酰胺、2-(2-羟基苯基)-1,3,5-三嗪、羟基胺、硝酮、β-硫代二丙酸酯,如例如USP 6,881,774中所述,该专利以引用方式并入本文。
当使用时,一种或多种抗氧化剂以有效量存在,如至多约10pph。优选的量为0.1至5pph,并且更优选的量为0.2至1.5pph。
在一些实施方案中,存在受阻胺光稳定剂(HALS)化合物。合适的HALS化合物包括双(1-辛氧基)-2,2,5,5-四甲基-4-哌啶基)癸二酸酯(来自巴斯夫(BASF)的TinuvinTM123)、正丁基-(3,5-二叔丁基-4-羟基苯甲基)双-(1,2,2,6-五甲基-4-哌啶基)丙二酸酯(来自巴斯夫的TinuvinTM144)、具有4-羟基-2-2,6,6-四甲基-1-哌啶醇的二甲基丁二酸酯聚合物(来自巴斯夫的TinuvinTM622)、双(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯(来自巴斯夫的TinuvinTM765)和双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯(来自巴斯夫的TinuvinTM770)等。
当使用时,HALS化合物以有效量存在,如至多约10pph。优选的量为0.1至5pph,并且更优选的量为0.1至2.5pph。
在发泡步骤期间可存在其它成分,包括例如填料、着色剂、气味掩蔽剂、阻燃剂、杀生物剂、抗静电剂、触变剂和开孔剂。
根据本发明,通过形成含有各种成分的反应混合物并且固化反应混合物来制造聚氨酯泡沫。可使用如连续块料生产方法的自由上升方法。可替代地,可使用模制方法。这类方法为众所周知的。通常,不需要改变常规加工操作来生产根据本发明的聚氨酯泡沫(除了包括结构I的3-氧代丙酰胺外)。
各种成分可单独地或以各种子组合形式引入混合头或其它混合装置中,在混合头或其它混合装置中将各种成分混合并且分配到将其固化的区域(如槽或其它开口容器,或闭合的模具)中。通常方便的是,尤其当制备模制泡沫时,形成含有以下的配制的多元醇组分:包括如可使用的交联剂和/或增链剂的一种或多种异氰酸酯反应性化合物、结构I的3-氧代丙酰胺化合物和其他添加剂(如果存在的话)以及任选的一种或多种催化剂、一种或多种表面活性剂和一种或多种发泡剂。然后使此配制的多元醇组分与多异氰酸酯(以及在配制的多元醇组分中不存在的任何其它成分)接触以产生泡沫。
各种组分中的一些或全部可在将其混合以形成反应混合物之前加热。在其它情况下,组分在大约环境温度(如15-40℃)下混合。在所有成分已经混合后,可对反应混合物施加热量,但这通常是不必要的。
固化反应的产物为软质聚氨酯泡沫。泡沫密度可为20至200kg/m3。对于大多数座椅和床上用品,优选的密度为24至80kg/m3。根据ASTM 3574-H的球回跳测试,泡沫的弹性可为至少50%。根据本发明生产的泡沫可用于例如缓冲应用,如床上用品和家用、办公室或车辆座椅,以及其它车辆应用,如头枕、仪表盘仪器面板、扶手、车顶内衬、噪音、振动和声振粗糙度(NVH)消减泡沫和吸音泡沫。
与其中结构I的3-氧代丙酰胺化合物不存在的情况相比,根据本发明制造的聚氨酯泡沫的特征在于醛,特别是甲醛、乙醛、丙烯醛和丙醛中的一种或多种的排放减少。用于测量甲醛、乙醛、丙烯醛和丙醛排放的合适的方法如下:将聚氨酯泡沫样品压碎以打开泡孔。将压碎的泡沫切割成10cm×10cm×14cm立方体样品,将其立即紧紧包装在铝箔或聚乙烯膜中,并且以此方式在约25℃下保持5天。
醛浓度根据Toyota TSM0508G测试方法进行测量。在那种Toyota方法中,将泡沫样品从箔或膜中取出,并且然后放置在先前已用氮气吹扫三次的单独的10L Tedlar气袋(中国德林有限公司(Delin Co.,Ltd.,China))中。将带有泡沫样品的袋用7L的氮气填充、密封并且在65℃加热两小时。将含有泡沫的塑料袋从烘箱中取出。袋中的气体被泵送通过350mg二硝基苯肼滤芯,以捕获羰基化合物。通过液相色谱法分析捕获的羰基化合物的甲醛、乙醛、丙烯醛和丙醛,其中结果以气袋中每立方米气体中相应醛的重量表示。在以下实施例中描述执行Toyota测试方法的特定方法的细节。
与在不存在结构I的3-氧代丙酰胺化合物的情况下生产的其它方面类似的泡沫相比,如在此方法中测定的甲醛、乙醛、丙烯醛和丙醛的排放量典型地都减少至少15%,通常至少50%,并且有时高达60至98%。本发明的一个优点是在一些或甚至所有这些醛化合物的排放量中可以看到显著减少。
在一些实施方案中,甲醛的排放量不大于200μg/m3,不大于150μg/m3或不大于100μg/m3,如根据Toyota方法所测量。在一些实施方案中,乙醛的排放量不大于100μg/m3,如根据Toyota方法所测量。在一些实施方案中,丙醛的排放量不大于100μg/m3,如根据Toyota方法所测量。
提供以下实施例来说明本发明,但并不旨在限制其范围。除非另外指明,否则所有的份数和百分比均按重量计。
实施例1和比较样品A
实施例1:将3g 1800当量的环氧丙烷和环氧乙烷的无规共聚物和200mg的N-(2-羟乙基)-3-氧代丁酰胺(HEOBA)混合。将0.2g混合物称重到顶空小瓶中并在100℃下调节10分钟。然后通过气相色谱/质谱分析顶部空间的乙醛和丙醛。
比较样品A:为了比较,无规共聚物样品本身以相同方式处理和分析。结果如表1中所示。醛浓度以每百万份无规共聚物的重量份数表示。
表1
发现HEOBA大大减少聚醚多元醇中的醛生成。
实施例2-4和比较样品B-F
一般发泡方法:配制的多元醇由40份标称羟基数为29.5的三官能聚醚多元醇、52.7份由蔗糖和甘油的混合物引发的1700当量聚醚多元醇、0.8份甘油、1.6份聚氨酯催化剂混合物、0.5份有机硅泡沫稳定表面活性剂和4.2份水组合来制备。聚氨酯泡沫由配制的多元醇通过将配制的多元醇与异氰酸酯封端的预聚物以1.8:1重量比组合,将所得反应混合物倒入杯中并且使反应混合物上升并固化以形成聚氨酯泡沫制成。在泡沫固化到足够尺寸稳定后,将其从杯中取出,并且除比较样品B和C外,切割10cm×10cm×14cm样品,重约38至41g。对于比较样品B和C,切割30g样品。立即将每个泡沫立方体包裹在铝箔中以形成密闭包装,持续7天。
比较样品B和C使用一般发泡方法制备。比较样品B在没有任何添加剂的情况下制备。在比较样品C中,在制备泡沫之前将0.1%三羟甲基丙烷三乙酰乙酸酯(AATMP)(基于配制的多元醇重量)加到配制的多元醇中。
比较样品D和实施例2以相同方式制备。比较样品D不含添加剂。在实施例2中,在制备泡沫之前将0.3%的HEOBA加到配制的多元醇中。
比较样品E和实施例3也以相同方式制备。比较样品E不含添加剂。在实施例3中,在制备泡沫之前将0.17%的HEOBA加到配制的多元醇中。
比较样品F和实施例4也以相同方式制备。比较样品F不含添加剂。在实施例4中,在制备泡沫之前将0.1%的HEOBA加到配制的多元醇中。
使用Toyota气袋法分析从泡沫样品排放的醛。在每种情况下,将立方形的泡沫样品从箔中取出,并且放入已用纯氮气洗涤三次并且排空的10L Tedlar气袋中。空的气袋用作空白。在将泡沫样品放入气袋中之后,将袋用约7L的氮气填充并且在65℃下的烘箱中加热2小时。然后通过气泵将气袋中的氮气抽出,并且分析甲醛、乙醛和丙醛。
来自每个袋的气体通过二硝基苯肼(DNPH)滤芯(CNWBOND DNPH-二氧化硅滤芯,350mg,分类号SEEQ-144102,Anple有限公司(Anple Co.,Ltd.)),采样速度为330毫升/分钟。从泡沫排放到气体中的醛被滤芯吸收,以形成DNPH衍生物。DNPH滤芯用3g乙腈洗脱,并且所得乙腈溶液通过HPLC进行分析,以如下所述定量样品中的羰基。
含有甲醛、乙醛、丙烯醛和丙醛各15μg/mL的标准溶液(在每种情况下均为DNPH衍生物的形式)(TO11A羰基-DNPH混合物,分类号48149-U,苏佩克有限公司(Supelco Co.,Ltd))用乙腈稀释。将含有2mL稀释溶液(甲醛、乙醛和丙醛各含有0.794ppm)的小瓶冷冻至-4℃。将冷冻溶液注入HPLC系统,并且分析甲醛、乙醛、丙烯醛和丙醛衍生物。根据下式从每种衍生物的洗脱峰面积计算响应因子:
其中响应因子i=衍生物i的响应因子;峰面积i=标准溶液中衍生物i的峰面积,并且0.794=标准溶液中每种衍生物的浓度。
然后确定每个泡沫样品释放的甲醛、乙醛、丙烯醛和丙醛的量。还测量了丙酮和挥发性有机化合物(TVOC)。在每种情况下,将通过洗脱DNPH柱获得的乙腈溶液注入HPLC系统,并且从每种衍生物中确定洗脱峰的面积。样品溶液中醛-DNPH衍生物的浓度计算如下:
其中:i的浓度=样品溶液中醛-DNPH衍生物的浓度,峰面积i=样品溶液中衍生物i的峰面积,并且响应因子i=衍生物i的响应因子,由如上所述的标准溶液确定。
HPLC条件如下:
比较样品BF和实施例2-4中的每一个的甲醛、乙醛、丙烯醛、丙酮和丙醛的浓度如表2-5所示。
表2
*不是本发明的实施例。
如表2中的数据所示,AATMP仅导致甲醛和乙醛排放量的少量减少。
表3
*不是本发明的实施例。
表4
*不是本发明的实施例。ND—未测定。
表5
*不是本发明的实施例。
如表3和表5中的数据所示,加入0.1至0.3%HEOBA导致甲醛、乙醛、丙醛、丙烯醛和丙酮排放量显著降低。
Claims (11)
3.根据权利要求1或2所述的方法,其中R1是苯基或具有至多6个碳原子的烷基,R2是氢,R3是2-羟乙基或2-羟丙基并且n是1。
4.根据权利要求3所述的方法,其中所述3-氧代丙酰胺是N-(2-羟乙基)-3-氧代丁酰胺。
5.一种在前述权利要求中任一项的方法中制备的聚氨酯泡沫。
7.根据权利要求6所述的方法,其中R1是苯基或具有至多6个碳原子的烷基,R2是氢,R3是2-羟乙基或2-羟丙基并且n是1。
8.根据权利要求7所述的方法,其中所述3-氧代丙酰胺是N-(2-羟乙基)-3-氧代丁酰胺。
10.根据权利要求9所述的聚醚多元醇,其中R1是苯基或具有至多6个碳原子的烷基,R2是氢,R3是2-羟乙基或2-羟丙基并且n是1。
11.根据权利要求10所述的聚醚多元醇,其中所述3-氧代丙酰胺是N-(2-羟乙基)-3-氧代丁酰胺。
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