CN109328208A - 多元醇中的聚酰胺分散体及其制备 - Google Patents
多元醇中的聚酰胺分散体及其制备 Download PDFInfo
- Publication number
- CN109328208A CN109328208A CN201780037426.6A CN201780037426A CN109328208A CN 109328208 A CN109328208 A CN 109328208A CN 201780037426 A CN201780037426 A CN 201780037426A CN 109328208 A CN109328208 A CN 109328208A
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- China
- Prior art keywords
- weight
- polyetheramine
- polyalcohol
- polyamide
- diamines
- 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.)
- Granted
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- 238000006243 chemical reaction Methods 0.000 claims description 29
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Abstract
本发明涉及一种制备多元醇中的聚酰胺分散体的方法、由此获得的多元醇中的聚酰胺分散体、聚醚胺在制备多元醇中的聚酰胺分散体中的用途、多元醇中的聚酰胺分散体用于制备聚氨酯的用途、各自的方法和聚氨酯。
Description
本发明涉及一种制备多元醇中的聚酰胺分散体的方法、由此获得的多元醇中的聚酰胺分散体、聚醚胺在制备多元醇中的聚酰胺分散体中的用途、多元醇中的聚酰胺分散体用于制备聚氨酯的用途、各自的方法和聚氨酯。
US 4,452,922涉及由二酯和二胺制得的聚酰胺共聚物多元醇以及由其制得的聚氨酯。聚酰胺共聚物多元醇由二羧酸二酯和二胺在聚醚多元醇的存在下反应制得。所形成的尼龙在多元醇中存在的量为1至30重量%。聚醚多元醇的分子量可为约2,000至8,000。聚酰胺共聚物多元醇可用于制造弹性体和软质聚氨酯泡沫,它们的特征在于良好的承载特性。根据实施例,草酸二乙酯与1,6-六亚甲基二胺在聚醚三醇中反应。在一个对比实施例中,使用分子量约为230的聚氧丙烯二胺(D-230)。但是,这使得多元醇相分离。可以得出结论,根据该专利的发明,含有醚键的二胺不能很好地起作用。
因此,从该文献中可以得出结论:聚醚胺使得形成的聚酰胺颗粒不稳定。
US 4,503,193涉及聚合物分散体及其用途。所述聚合物分散体在自由基聚合引发剂和聚酰胺稳定剂的存在下,由烯键式不饱和单体或单体的混合物在扩链剂中的原位聚合制得。作为扩链剂,使用脂族和/或芳脂族二醇。聚酰胺稳定剂为聚(N-乙烯基-2-吡咯烷酮)(PVP)。根据实施例,1,4-丁二醇、PVP、丙烯腈和苯乙烯反应形成聚合物分散体。
US 4,523,025涉及来自部分反应的多胺的聚合物多元醇。所述聚合物多元醇由部分反应的多胺与有机多异氰酸酯在分子量约为3,000至8,000的聚醚多元醇中反应制得。优选地,多异氰酸酯与部分烷氧基化的聚氧化亚烷基二胺反应。根据实施例1,制备聚氧丙烯二胺(D-230)的环氧乙烷/环氧丙烷加合物,其进一步与高反应性的基于甘油的三醇(SF-5505)和甲苯二异氰酸酯反应。所得产物为白色、不透明的粘性分散体。所产生的聚脲颗粒分散于多元醇中。
本发明的目的在于提供一种制备多元醇中的聚酰胺分散体的方法,其产生稳定的分散体,所述分散体是稳定的并且在长时间内不会发生相分离。
此外,应提供可以容易地与多异氰酸酯反应形成聚氨酯、特别是具有增强的刚性和更高的热稳定性和化学稳定性、特别是抗水解的聚氨酯泡沫的多元醇中的聚酰胺分散体。
该目的通过制备多元醇中的聚酰胺分散体的方法来实现,通过在反应器中将摩尔比为1.1:0.9至0.9:1.1的二胺与二羧酸组分在多元醇组分中反应,二胺组分含有10至100重量%的至少一种聚醚胺,所述聚醚胺为数均分子量(Mn)为500至5,000g/mol的二官能伯胺,多元醇组分的数均分子量(Mn)为2,000至8,000g/mol,其中在反应开始时在反应器中提供至多80重量%的二胺组分,并在反应过程中向反应器中逐步或连续加入至少20重量%的二胺组分。
此外,该目的通过可由上述方法获得的多元醇中的聚酰胺分散体来实现。
此外,该目的通过多元醇中的聚酰胺分散体来实现,其中所述聚酰胺基于二胺组分和二羧酸组分,10至100重量%的二胺组分为数均分子量(Mn)为500至5,000g/mol的至少一种聚醚胺。
此外,该目的通过聚醚胺作为在二羧酸和二胺在多元醇中的原位缩聚反应中用于聚酰胺的反应性稳定剂的用途而实现,所述聚醚胺为数均分子量(Mn)为500至5,000g/mol的二官能伯胺。
此外,该目的通过制备聚氨酯的方法来实现,所述方法包括将如上所定义的多元醇中的聚酰胺分散体和多异氰酸酯,以及如果合适,一种或多种具有对异氰酸酯呈反应性的氢原子的其他化合物、扩链剂和/或交联剂、催化剂、发泡剂和其他添加剂混合,并将所述混合物反应形成聚氨酯。
此外,该目的通过可由上述方法获得的聚氨酯来实现。
与US 4,452,922的发现相反,根据本发明,发现当二胺组分和二羧酸组分在多元醇中反应形成聚酰胺时,聚醚胺——其为数均分子量(Mn)为500至5,000g/mol的二官能伯胺——稳定形成的聚酰胺颗粒。
对于数均分子量(Mn)为1,000至3,000g/mol,更优选1,500至2,500g/mol,特别是约2,000g/mol的聚醚胺来说,稳定效果特别显著。
通过使用这些高分子量的聚醚胺,可以形成均匀稳定的聚酰胺颗粒在多元醇中的分散体。聚醚胺可以视为反应性稳定剂,因为其可以与二羧酸反应成为聚酰胺链的一部分。
根据本发明使用的至少一种聚醚胺可以形成10至100重量%的二胺组分,优选20至80重量%,更优选40至60重量%,例如约50重量%的二胺组分。
对于本发明使用的所有组分,特别是聚醚胺和多元醇组分,数均分子量优选通过GPC使用聚苯乙烯标准物来测定。合适的溶剂为间甲酚,如果需要,其与二氯甲烷或氯苯或TMF混合。
聚醚胺为二官能的伯胺,其中两个伯氨基可以与二羧酸组分的羧酸基团反应形成酰胺键。
优选地,两个伯氨基位于末端位置,并且聚醚胺的特征在于在主链中重复氧亚乙基和/或氧亚丙基单元。优选地,该主链不是支化的而是直链的。
除了重复的氧亚乙基和/或氧亚丙基单元以外,聚醚胺还可含有起始剂分子,其上接枝氧亚丙基和/或氧亚乙基单元。
典型的起始剂分子可以为双官能醇或其他双官能化合物,其上可以接枝环氧乙烷和/或环氧丙烷。
少量的具有较高的胺官能的聚醚胺可以和二官能伯胺的聚醚胺一起使用。优选地,这种较高级的聚醚胺可以是三官能伯胺。
优选地,基于所使用的总的聚醚胺计,不超过5重量%,更优选不超过1重量%具有超过两个伯氨基。最优选地,全部的聚醚二胺组分由二官能伯胺组成。
聚醚胺的典型结构可以是具有经调整的较高分子量的D-230和D-403的那些。根据本发明可以使用的聚醚胺的一个实例是BASF SE的聚醚胺D 2000(EC 303)。该聚醚胺的数均分子量为约2,000g/mol。
如果使用氧亚丙基单元和氧亚乙基单元,则它们可以交替、连续或以混合物或嵌段的形式使用。
根据本发明使用的聚醚胺可以由例如BASF SE获得或可以借助聚醚醇与氨的胺化来制备。聚醚醇可以通过使用例如KOH或DMC催化剂聚合环氧乙烷或环氧丙烷来获得。
根据本发明使用的二胺组分含有10至100重量%、更优选20至80重量%、最优选40至60重量%,例如约50重量%的至少一种聚醚胺。
二胺和二羧酸组分可分别由一种或多种类型的二胺或二羧酸组成。因此,除了上述聚醚胺以外,在二胺组分中还可存在其他二胺。
重要的是二胺和二羧酸组分以1.1:0.9至0.9:1.1,优选1.05:0.95至0.95:1.05,更优选近似1:1的摩尔比使用,即近似于化学计量比。
可以使用的二羧酸为具有6至12个、特别是6至10个碳原子的链烷二羧酸和芳族二羧酸。此处仅可提及的几种酸是己二酸、壬二酸、癸二酸、十二烷二酸和对苯二甲酸和/或间苯二甲酸。
特别合适的二胺为具有6至12个,特别是6至8个碳原子的链烷二胺,以及间苯二甲胺、二(4-氨基苯基)甲烷、二(4-氨基环己基)甲烷、2,2-二(4-氨基苯基)丙烷、2,2-二(4-氨基环己基)丙烷,或1,5-二氨基-2-甲基戊烷。
除了通过二羧酸与二胺反应获得的聚酰胺以外,实例还有共聚酰胺,其另外衍生自具有7至13个环原子的内酰胺,例如己内酰胺、辛内酰胺和十二内酰胺。
优选的聚酰胺为聚己二酰己二胺、聚六亚甲基癸二酰胺,以及尼龙-6/6,6共聚酰胺,特别是具有5至95重量%的己内酰胺单元。
其他合适的聚酰胺还通过在水的存在下的所谓直接聚合而含有来自ω-氨基烷基腈的单元,例如氨基己腈(PA 6),以及带有六亚甲基二胺的己二腈(PA 66),例如记载于DE-A 10313681、EP-A 1198491和EP 922065中。
还可提及可通过例如1,4-二氨基丁烷与己二酸在升高的温度下缩合获得的聚酰胺(尼龙-4,6)。所述结构的聚酰胺的制备方法例如记载于EP-A38 094、EP-A 38 582和EP-A39 524中。
其他合适的聚酰胺为可通过两种或更多种上述单体共聚合获得的那些,或任意期望的混合比的多种聚酰胺的混合物。
此外,已证明半芳族共聚酰胺例如PA 6/6T和PA 66/6T是合适的,它们的三胺含量低于0.5重量%,优选低于0.3重量%(参见EP-A 299 444和EP-A 667 367)。
合适的共聚酰胺由以下物质组成:
A1)20至90重量%的衍生自对苯二甲酸和六亚甲基二胺的单元,
A2)0至50重量%的衍生自ε-己内酰胺的单元,以及
A3)0至80重量%的衍生自己二酸和六亚甲基二胺的单元,
A4)0至40重量%的其他形成聚酰胺的单体,其中组分(A2)或(A3)或(A4)的比例或它们的混合物的比例为至少10重量%。
组分A1)包含20至90重量%的衍生自对苯二甲酸和六亚甲基二胺的单元。
除了衍生自对苯二甲酸和六亚甲基二胺的单元外,所述共聚酰胺还包含——如果合适——衍生自ε-己内酰胺的单元,和/或衍生自己二酸和六亚甲基二胺的单元和/或衍生自其他形成聚酰胺的单体的单元。
芳族二羧酸A4)具有8至16个碳原子。合适的芳族二羧酸的实例为间苯二甲酸;取代的对苯二甲酸和取代的间苯二甲酸,例如3-叔丁基间苯二甲酸;多核的二羧酸,例如4,4'-二苯基二羧酸和3,3'-二苯基二羧酸、4,4'-二苯基甲烷二羧酸和3,3'-二苯基甲烷二羧酸、4,4'-二苯砜二羧酸和3,3'-二苯砜二羧酸、1,4-萘二羧酸或2,6-萘二羧酸,或苯氧基对苯二甲酸,此处特别优选间苯二甲酸。
其他形成聚酰胺的单体A4)可衍生自具有4至16个碳原子的二羧酸和具有4至16个碳原子的脂族或脂环族二胺,或衍生自氨基羧酸,以及衍生自对应的具有7至12个碳原子的内酰胺。仅可提及这些类型的几种合适的单体:辛二酸、壬二酸或癸二酸作为脂族二羧酸的代表,1,4-丁二胺、1,5-戊二胺、哌嗪、4,4'-二氨基二环己基甲烷、2,2-(4,4'-二氨基二环己基)丙烷、3,3'-二甲基-4,4'-二氨基二环己基甲烷或或间苯二甲胺作为二胺的代表,以及辛内酰胺、庚内酰胺、ω-氨基十一烷酸和十二内酰胺作为内酰胺的代表和氨基羧酸的代表。
这种聚酰胺在DE-A-10 2009 011 668中公开。
以下不全面的列表包含提及的聚酰胺A)和用于本发明目的的其他聚酰胺,以及所包含的单体。
AA/BB聚合物:
PA 46 四亚甲基二胺、己二酸
PA 66 六亚甲基二胺、己二酸
PA 69 六亚甲基二胺,壬二酸
PA 610 六亚甲基二胺、癸二酸
PA 612 六亚甲基二胺、癸烷二羧酸
PA 613 六亚甲基二胺、十一烷二羧酸
PA 1212 1,12-十二烷二胺、癸烷二羧酸
PA 1313 1,13-二氨基十三烷、十一烷二羧酸
PA 6T 六亚甲基二胺、对苯二甲酸
PA MXD6 间苯二甲胺、己二酸
其他的共聚单体:
PA 4 吡咯烷酮
PA 6 ε-己内酰胺
PA 7 乙内酰胺(Ethanolactam)
PA 8 辛内酰胺
PA 9 9-氨基壬酸
PA 11 11-氨基十一烷酸
PA 12 十二内酰胺
AA/BB聚合物
PA 6I 六亚甲基二胺、间苯二甲酸
PA 6-3-T 三甲基六亚甲基二胺、对苯二甲酸
PA 6/6T (参见PA 6和PA 6T)
PA 6/66 (参见PA 6和PA 66)
PA 6/12 (参见PA 6和PA 12)
PA 66/6/610 (参见PA 66、PA 6和PA 610)
PA 6I/6T (参见PA 6I和PA 6T)
PA PACM 12二氨基二环己基甲烷、十二内酰胺
PA 6I/6T/PACMT 为PA 6I/6T+二氨基二环己基甲烷、对苯二甲酸
PA 6T/6I/MACMT为PA 6I/6T+二甲基二氨基环己基甲烷、对苯二甲酸
PA 6T/6I/MXDT 为PA 6I/6T+间苯二甲胺、对苯二甲酸
PA 12/MACMI 十二内酰胺、二甲基二氨基二环己基甲烷、间苯二甲酸
PA 12/MACMT 十二内酰胺、二甲基二氨基二环己基甲烷、对苯二甲酸
PA PDA-T 苯二胺、对苯二甲酸。
聚酰胺的分子量可以使得聚酰胺的特性粘度通常为90至350ml/g,优选110为240ml/g,所述特性粘度在25℃下根据ISO 307以在96重量%浓度的硫酸中的0.5重量%浓度的溶液形式测定。
优选分子量(重均)为至少5,000的半结晶或无定形的树脂,其实例为记载于美国专利2 071 250、2 071 251、2 130 523、2 130 948、2 241 322、2 312 966、2 512 606和3393 210中的那些。
最优选地,己二酸用作二羧酸。此外,最优选地,六亚甲基二胺用作除聚醚胺以外的另外的二胺组分。还优选除聚醚胺以外不使用另外的二胺组分。
本发明使用的多元醇组分的数均分子量(Mn)为2,000至8,000g/mol,优选3,000至7,000g/mol,最优选4,000至6,000g/mol,例如约5,000g/mol。
本发明的多元醇组分可以由一种或多种不同的多元醇组成。多元醇可以例如为聚酯多元醇或更优选为聚醚醇。还可以使用聚合物改性的多元醇。合适的多元醇例如公开于WO 2013/030173中,特别是在第7至8页。最优选聚醚醇。
聚醚醇通过已知的方法制备,例如,由一种或多种在亚烷基部分具有2至4个碳原子的环氧烷烃使用碱金属氢氧化物或碱金属醇盐作为催化剂,加入至少一种包含2或3个结合形式的反应性氢原子的起始剂分子,通过阴离子聚合来制备;或使用路易斯酸例如五氯化锑或氟化硼醚化物的阳离子聚合来制备。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,优选环氧乙烷和1,2-环氧丙烷。此外,已知为DMC催化剂的多金属氰化物也可以用作催化剂。环氧烷烃可以单独使用、连续交替使用或以混合物的形式使用。优选1,2-环氧丙烷和环氧乙烷的混合物,其中环氧乙烷末端嵌段形式(“EO帽”)的环氧乙烷的用量为10至50%,从而使得形成的多元醇具有大于70%的伯OH端基。
可能的起始剂分子为水或2官能醇和3官能醇例如乙二醇、1,2-和1,3-丙二醇、二乙二醇、二丙二醇、1,4-丁二醇、丙三醇或三羟甲基丙烷。其他可能的起始剂为4至8官能的醇,如糖、山梨糖醇或季戊四醇。
优选地,所述多元醇为聚醚醇,由至少一种包含2至8个反应性氢原子的起始剂分子和一种或多种在亚烷基中具有2至4个碳原子的环氧烷烃制备。
聚醚多元醇,优选聚氧丙烯-聚氧乙烯多元醇,具有2至3的官能度。
聚酯多元醇可以例如由具有2至12个碳原子的有机二羧酸、优选具有4至6个碳原子的脂族二羧酸,和多元醇、优选具有2至12个碳原子、优选2至6个碳原子的二醇制得。可能的二羧酸的实例为:琥珀酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、十二烷二酸、马来酸、富马酸、邻苯二甲酸、间苯二甲酸和对苯二甲酸。所述二羧酸可以单独使用或彼此混合使用。代替游离的二羧酸,可以使用相应的二羧酸衍生物,例如具有1至4个碳原子的醇的二羧酸酯或二羧酸酐。优选使用重量比例如为20-35:35-50:20-32的琥珀酸、戊二酸和己二酸的二羧酸混合物,且特别是己二酸。二元醇和多元醇、特别是二醇的实例为: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、丙三醇和三羟甲基丙烷。优选使用乙二醇、二乙二醇、1,4-丁二醇、1,5-戊二醇和1,6-己二醇。还可以使用衍生自内酯的聚酯多元醇,例如ε-己内酯,或羟基羧酸,例如ω-羟基己酸。
为了制备聚酯多元醇,有机(例如芳族且优选脂族)多羧酸和/或衍生物和多元醇可以在不存在催化剂的情况下或优选在酯化催化剂的存在下,有利地在惰性气体气氛下,例如氮气、一氧化碳、氦气、氩气等,在熔体中在150-250℃,优选180至220℃的温度下,如果合适,在减压下缩聚至期望的酸值,所述酸值优选小于10,特别优选小于2。在一个优选的实施方案中,酯化反应混合物在上述温度下,在大气压下以及随后在低于500mbar,优选50至150mbar的气压下缩聚至80至30,优选40至30的酸值。可能的酯化反应催化剂为金属、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。然而,缩聚还可以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,以共沸蒸馏出缩合水。为了制备聚酯多元醇,有机多羧酸和/或衍生物和多元醇有利地以1:1-1.8,优选1:1.05-1.2的摩尔比进行缩聚。
所得的聚酯多元醇优选地具有2至4,特别是2至3的官能度。
可以使用包含聚醚醇和聚酯醇的混合物。
其他合适的多元醇为聚合物改性的多元醇,优选聚合物改性的聚酯醇或聚醚醇,特别优选接枝的聚醚或接枝的聚酯醇,特别是接枝的聚醚醇。这些是聚合物多元醇,其通常具有5至60重量%,优选10至55重量%,特别优选30至55重量%,且特别是40至50重量%的优选热塑性聚合物。这些聚合物聚酯醇例如记载于WO 05/098763和EP-A-250 351中,并通常通过合适的烯烃单体在用作接枝基质的聚酯醇中进行的自由基聚合来制得,所述烯烃单体例如为苯乙烯、丙烯腈、(甲基)丙烯酸酯、(甲基)丙烯酸和/或丙烯酰胺。侧链通常通过将自由基从生长的聚合物链转移至聚酯醇或聚醚醇中而形成。除了接枝共聚物以外,聚合物多元醇主要包含分散在未改变的聚酯醇或聚醚醇中的烯烃的均聚物。
在一个优选的实施方案中,丙烯腈、苯乙烯、丙烯腈和苯乙烯、特别优选只有苯乙烯用作单体。所述单体如果合适在其他单体、大分子单体、缓和剂和自由基引发剂、通常偶氮或过氧化物的存在下,在作为连续相的聚酯醇或聚醚醇中进行聚合。该方法记载于例如DE 111 394、美国专利3,304,273、美国专利3,383,351、美国专利3,523,093、DE 1 152 536和DE 1 152 537中。
在自由基聚合期间,将大分子单体引入共聚物链中。这导致嵌段共聚物的形成,所述嵌段共聚物具有聚酯或聚醚嵌段和聚丙烯腈-苯乙烯嵌段,并在连续相和分散相的界面用作相相容剂,以及抑制聚合物聚酯醇颗粒的聚集。大分子单体的比例通常为1至20重量%,基于用于制备聚合物多元醇的单体的总重量计。
如果在多元醇组分中包含聚合物多元醇,则其优选与其他多元醇,例如聚醚醇、聚酯醇或聚醚醇或聚酯醇的混合物共同存在。聚合物多元醇的比例特别优选大于5重量%,基于多元醇组分的总重量计。可以包含的聚合物多元醇的量例如为7至90重量%或11至80重量%,基于多元醇组分的总重量计。所述聚合物多元醇特别优选为聚合物聚酯醇或聚合物聚醚醇。
优选地,多元醇组分的量为20至80重量%,更优选30至70重量%,最优选40至60重量%,例如约50重量%,基于二胺和二酸组分和多元醇组分的总和计。
本发明的多元醇中的聚酰胺分散体通过在反应器中将二胺和二羧酸组分在多元醇组分中进行反应制得。在反应开始时,在反应器中提供至多80重量%,更优选至多60重量%,最优选至多50重量%的二胺组分,并且在反应过程中向反应器中逐步(逐渐地或连续地)加入至少20重量%,更优选至少40重量%,最优选至少50重量%的二胺组分。因此,在反应开始时反应混合物中仅存在部分二胺组分,并且随着反应的进行连续或间隔地加入剩余的二胺组分。
优选地,二胺组分含有20至80重量%,更优选40至60重量%,最优选约50重量%的至少一种聚醚胺和20至80重量%,更优选40至60重量%,最优选约50重量%的一种或多种不同于聚醚胺的二胺,在加入至少一种聚醚胺之后向反应器中加入至少部分的二胺。
如果仅使用聚醚胺作为二胺组分,则如上所述,在反应过程中将部分的聚醚胺逐步或连续加入反应器中。但是,如果使用大量的其他二胺,则优选在反应器中提供聚醚胺,并在反应过程中向反应器中逐步或连续添加其他二胺,或在反应器中与聚醚胺一起提供部分的不同的二胺,并在反应过程中逐步或连续地加入剩余的其他二胺。
这使得聚醚胺能够以最好的方式用作形成聚酰胺的稳定剂。
可以在反应开始时在反应器中提供二羧酸组分,这是优选的。还可以在反应开始时在反应器中仅提供部分的二羧酸组分,并在反应过程中逐步或连续地加入剩余的二羧酸组分,例如伴随着加入或施用二胺组分。
二胺与二羧酸组分的反应优选在200至300℃,更优选220至280℃,最优选230至250℃范围内的温度下进行。反应可在惰性气体气氛中进行。优选在搅拌下进行反应。在加入二胺组分后,优选在反应温度下继续搅拌一段时间以使得反应结束。然后,将反应混合物冷却并在室温下保持稳定数周。
本发明还涉及多元醇中的聚酰胺分散体,其中聚酰胺基于二胺和二羧酸组分,10至100重量%的二胺组分为数均分子量(Mn)为500至5,000g/mol的至少一种聚醚胺。
聚酰胺分散体的其他特征可如上所定义。优选地,多元醇组分的数均分子量(Mn)为2,000至8,000g/mol。
本发明还涉及如上所定义的聚醚胺在二羧酸和二胺于多元醇中的原位缩聚中作为用于聚酰胺的反应稳定剂的用途。对于该用途,优选在反应开始时在反应器中提供聚醚胺,从而在反应开始时就可以实现稳定效果。
如上所述的多元醇中的聚酰胺分散体可以用于制备聚氨酯,优选聚氨酯泡沫。
通常,一种用于制备聚氨酯的方法包括将如上所述的多元醇中的聚酰胺分散体与多异氰酸酯和——如果合适——一种或多种或其他的具有对异氰酸酯呈反应性的氢原子的化合物、扩链剂和/或交联剂、催化剂、发泡剂和其他添加剂混合,并将混合物反应形成聚氨酯。
优选地,所述聚氨酯为聚氨酯泡沫,并且所述混合物包含发泡剂。通常,所述混合物含有催化剂和交联剂以获得稳定的泡沫。
聚氨酯通过多异氰酸酯与具有对异氰酸酯呈反应性的氢原子的化合物反应形成。具有对异氰酸酯呈反应性的氢原子的化合物的一部分为多元醇中的聚酰胺分散体。多元醇中的聚酰胺分散体形成了在形成聚氨酯的反应中使用的所有多元醇、催化剂和交联剂的总和的5至90重量%,更优选7至70重量%,最优选10至50重量%。
不仅本发明的分散体中的多元醇对多异氰酸酯呈反应性,聚酰胺中的氨基对多异氰酸酯也呈反应性。因此,形成组合的聚氨酯,其中多异氰酸酯也与聚酰胺反应,并且如果除了与聚酰胺反应外仍存在的话,还与聚醚胺反应。
根据本发明,聚氨酯,优选热塑性聚氨酯,优选通过将异氰酸酯与对异氰酸酯呈反应性的且分子量为500至10,000的化合物和——如果合适——分子量为50至499的扩链剂如果合适在催化剂和/或常规助剂和/或添加剂的存在下反应制得。
作为有机异氰酸酯,可以使用通常已知的脂族、脂环族、芳脂族和/或芳族异氰酸酯,优选二异氰酸酯,例如三亚甲基二异氰酸酯、四亚甲基二异氰酸酯、五亚甲基二异氰酸酯、六亚甲基二异氰酸酯、七亚甲基二异氰酸酯和/或八亚甲基二异氰酸酯、2-甲基五亚甲基1,5-二异氰酸酯、2-乙基亚丁基1,4-二异氰酸酯、五亚甲基1,5-二异氰酸酯、亚丁基1,4-二异氰酸酯、1-异氰酸酯基-3,3,5-三甲基-5-异氰酸酯基甲基环己烷(异佛尔酮二异氰酸酯,IPDI)、1,4-和/或1,3-双(异氰酸酯基甲基)环己烷(HXDI)、环己烷1,4-二异氰酸酯、1-甲基环己烷2,4-和/或2,6-二异氰酸酯和/或二环己基甲烷4,4’-,2,4’-和2,2’-二异氰酸酯、二苯基甲烷2,2’-、2,4’-和/或4,4’-二异氰酸酯(MDI)、萘1,5-二异氰酸酯(NDI)、甲苯2,4-和/或2,6-二异氰酸酯(TDI)、二苯基甲烷二异氰酸酯、3,3’-二甲基二苯基二异氰酸酯、1,2-二苯基乙烷二异氰酸酯和/或亚苯基二异氰酸酯。
作为除多元醇中的聚酰胺分散体外对异氰酸酯呈反应性的化合物,可以使用通常已知的对异氰酸酯呈反应性的化合物及其混合物,例如聚酯醇、聚醚醇和/或聚碳酸酯二醇,它们通常统称为“多元醇”,其数均分子量(Mn)为500至8,000g/mol,优选600至6,000g/mol,特别是800至4,000g/mol,且优选平均官能度为1.8至2.3,优选1.9至2.2,特别是2。
在一个特别优选的实施方案中,对异氰酸酯呈反应性的化合物为数均分子量为600至2,500g/mol的聚四氢呋喃。
在另一个特别优选的实施方案中,对异氰酸酯呈反应性的化合物为聚酯醇,优选聚酯二醇,优选基于己二酸和1,4-丁二醇的那些,它们的数均分子量为500至2,500g/mol,特别优选600g/mol至900g/mol。
作为扩链剂,可以使用通常已知的分子量为50至499的脂族、芳脂族、芳族和/或脂环族化合物,优选2官能的化合物,例如在亚烷基中具有2至10个碳原子的二胺和/或链烷二醇,特别是1,4-丁二醇、1,6-己二醇和/或具有3至8个碳原子的二亚烷基、三亚烷基、四亚烷基、五亚烷基、六亚烷基、七亚烷基、八亚烷基、九亚烷基和/或十亚烷基二醇,优选相应的低聚丙二醇和/或聚丙二醇,还可以使用扩链剂的混合物。
作为特别是加速二异氰酸酯的NCO基团和形成组分的羟基之间的反应的合适的催化剂,可以使用本领域已知和常用的叔胺,例如三乙胺、二甲基环己胺、N-甲基吗啉、N,N′-二甲基哌嗪、2-(二甲基氨基乙氧基)乙醇、二氮杂二环[2.2.2]辛烷等,且特别地还有有机金属化合物例如钛酸酯,铁化合物例如乙酰丙酮铁(III),锡化合物例如二乙酸锡、二辛酸锡、二月桂酸锡或脂族羧酸的二烷基锡盐例如二乙酸二丁基锡、二月桂酸二丁基锡等。催化剂的用量通常为0.0001至0.1重量份/100重量份的多羟基化合物。
除了催化剂以外,还可以向形成组分中加入常规助剂和/或添加剂。可提及的实例为发泡剂、表面活性剂、填料、阻燃剂、成核剂、氧化稳定剂、润滑剂和脱模剂、染料和颜料,如果合适,除了本发明使用的稳定剂混合物以外的其他稳定剂例如抗水解、光、热或变色的稳定剂、无机填料和/或有机填料、增强材料和增塑剂。
还可以使用链调节剂,通常是分子量为31至499g/mol的那些。这种链调节剂为仅具有一个对异氰酸酯呈反应性的官能团的化合物,例如单官能的醇、单官能的胺和/或单官能的多元醇。这种链调节剂能够以想要的方式设定特定的流动性能,特别是在TPU的情况下。链调节剂的用量通常可以为0至5重量份,优选0.1至1重量份,基于100重量份的对异氰酸酯呈反应性的组分计。
反应可以在常规的指数下进行,优选在60至120的指数下,特别优选在80至110的指数下进行。所述指数定义为反应中使用的组分的总的异氰酸酯基团与对异氰酸酯呈反应性的基团即活性氢的比值。在指数为100时,存在一个活性氢原子,即相对于组分的每一个异氰酸酯基团存在一个对异氰酸酯呈反应性的基团。在低于100的指数下,存在比OH基团更多的异氰酸酯基团。
为了形成聚氨酯泡沫和其他可能的成分,如TPU粒料和可膨胀的颗粒,可参考US2010/0047550。
例如,发泡剂在该文献中公开于第[0070]部分。其他催化剂公开于第[0068]和[0069]部分。包含物理发泡剂的中空微球公开于第[0072]至[0074]部分。可能的表面活性物质、脱模剂和填料公开于该文献的第[0076]至[0079]部分。
通过以下实施例进一步说明本发明。
实施例
实施例1(逐步和化学计量添加胺)
在2.5L玻璃反应器中提供6.9g(47mmol)己二酸和400g的三官能的高活性的聚醚多元醇(BASF SE的),所述多元醇具有基于丙三醇的伯羟基端基和具有14重量%EO嵌段的PO/EO嵌段。在用氮气吹扫反应器后,在搅拌和恒定的氮气流下将内容物加热至240℃。在达到反应温度后,通过滴液漏斗加入93g(47mmol)数均分子量约为2,000g/mol的聚醚胺(二官能伯胺)(BASF SE的EC 303)。待EC 303添加结束后,将反应混合物在240℃下再保持15分钟。随后,将反应混合物冷却至80℃。获得储存数周后仍保持均匀的澄清的溶液。
实施例2(和六亚甲基二胺作为氨基组分)
在2.5L玻璃反应器中提供12.1g(83mmol)己二酸、83.0g(41mmol)EC303和400g在用氮气吹扫反应器后,在搅拌和恒定的氮气流下将内容物加热至180℃。在达到反应温度后,用滴液漏斗滴加4.8g(41mmol)六亚甲基二胺。在加入六亚甲基二胺后,将反应混合物在180℃下再保持30分钟。随后将反应混合物冷却至80℃。将产物稳定数周。
对比实施例3(在反应器中提供所有的反应物)
在2.5L玻璃反应器中提供6.9g(47mmol)己二酸、93g(47mmol)EC303和400g在用氮气吹扫反应器后,在搅拌和恒定的氮气流下将反应器的成分加热至240℃。在达到反应温度后,将混合物在240℃下再保持30分钟。随后将反应混合物冷却至80℃。获得在数天后显示相分离的溶液。产物的粘度为1,398mPa·s(25℃)。
对比实施例4(非化学计量)
在2.5L玻璃反应器中提供6.6g(45mmol)己二酸和400g在用氮气吹扫反应器后,在搅拌和恒定的氮气流下将混合物加热至240℃。在达到反应温度后,用滴液漏斗缓慢滴加2.64g(23mmol)六亚甲基二胺和91g(45mmol)EC 303的混合物。之后,将反应混合物在240℃下再保持15分钟。随后,将反应混合物冷却至80℃。获得在数天后显示相分离的溶液。产物的粘度为1,206mPa·s(25℃)。
测试软质泡沫
多元醇组分通过将不同量的来自实施例1的多元醇与下表所示(重量份)的其他多元醇、催化剂和添加剂混合来制备。将多元醇组分与合适量的MDI共混物(NCO值为32.8%)手动混合,以达到95的异氰酸酯指数并将它们倒入模具中固化形成软质泡沫。
根据DIN EN ISO 845测定密度,根据DIN EN ISO 3386-1测定抗压强度。
催化剂1为33重量%的三亚乙基二胺于二丙二醇中的溶液。
催化剂2为N,N,N’-三甲基-N’-羟乙基二氨基乙基醚。
稳定剂1为硅氧烷表面活性剂。
稳定剂2为硅氧烷稳定剂。
Claims (14)
1.一种制备多元醇中的聚酰胺分散体的方法,其通过在反应器中将摩尔比为1.1:0.9至0.9:1.1的二胺与二羧酸组分在多元醇组分中反应而进行,二胺组分含有10至100重量%的至少一种聚醚胺,所述聚醚胺为数均分子量(Mn)为500至5,000g/mol的二官能伯胺,多元醇组分的数均分子量(Mn)为2,000至8,000g/mol,其中在反应开始时在反应器中提供至多80重量%的二胺组分,并在反应过程中向反应器中逐步或连续加入至少20重量%的二胺组分。
2.根据权利要求1所述的方法,其中二胺组分含有20至80重量%的至少一种聚醚胺和20至80重量%的一种或多种不同于该聚醚胺的二胺,在加入该至少一种聚醚胺之后向反应器中加入至少部分的该二胺。
3.根据权利要求1或2所述的方法,其中多元醇组分的量为20至80重量%,基于二胺组分和二酸组分和多元醇组分的总和计。
4.根据权利要求1至3中任一项所述的方法,其中所述聚醚胺的特征在于在主链中重复的氧亚乙基和/或氧亚丙基单元以及末端的伯氨基。
5.根据权利要求1至4中任一项所述的方法,其中所述多元醇为聚醚醇,所述聚醚醇由至少一种包含2至8个反应性氢原子的起始剂分子和一种或多种在亚烷基中具有2至4个碳原子的环氧烷烃制备。
6.根据权利要求1至5中任一项所述的方法,其中在反应开始时在反应器中提供二羧酸组分。
7.多元醇中的聚酰胺分散体,其可通过权利要求1至6中任一项所述的方法获得。
8.多元醇中的聚酰胺分散体,其中聚酰胺基于二胺和二羧酸组分,10至100重量%的二胺组分为至少一种聚醚胺,所述聚醚胺的数均分子量(Mn)为500至5,000g/mol。
9.根据权利要求8所述的聚酰胺分散体,其中多元醇组分的数均分子量(Mn)为2,000至8,000g/mol。
10.聚醚胺在二羧酸和二胺于多元醇中的原位缩聚中作为用于聚酰胺的反应稳定剂的用途,所述聚醚胺为二官能的伯胺,其数均分子量(Mn)为500至5,000g/mol。
11.权利要求7至9中任一项所述的多元醇中的聚酰胺分散体用于制备聚氨酯的用途。
12.一种制备聚氨酯的方法,其包括将权利要求7至9中任一项所述的多元醇中的聚酰胺分散体或通过权利要求1至6中任一项所述的方法制得的多元醇中的聚酰胺分散体和多异氰酸酯以及——如果合适——一种或多种具有对异氰酸酯呈反应性的氢原子的其他化合物、扩链剂和/或交联剂、催化剂、发泡剂和其他添加剂混合,并将混合物反应形成聚氨酯。
13.根据权利要求12所述的方法,其中聚氨酯为聚氨酯泡沫,并且所述混合物包含发泡剂。
14.聚氨酯,其可通过权利要求12或13所述的方法获得。
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CN114514262A (zh) * | 2019-11-11 | 2022-05-17 | 株式会社吴羽 | 聚酰胺的制造方法以及聚酰胺 |
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US20190177467A1 (en) | 2019-06-13 |
MX2018015767A (es) | 2019-08-29 |
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WO2017216209A1 (en) | 2017-12-21 |
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