CN102066457A - C11二醇或c11二醇混合物在生产聚合物中的用途 - Google Patents
C11二醇或c11二醇混合物在生产聚合物中的用途 Download PDFInfo
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- CN102066457A CN102066457A CN2009801227626A CN200980122762A CN102066457A CN 102066457 A CN102066457 A CN 102066457A CN 2009801227626 A CN2009801227626 A CN 2009801227626A CN 200980122762 A CN200980122762 A CN 200980122762A CN 102066457 A CN102066457 A CN 102066457A
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- Prior art keywords
- propyl group
- polymkeric substance
- ammediol
- mixture
- glycol
- Prior art date
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- 239000000126 substance Substances 0.000 claims description 58
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- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 claims description 47
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 46
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Abstract
本发明涉及可通过单体化合物缩聚或加聚获得的聚合物,其特征在于作为单体化合物使用式(I)的2-(2-甲基)丁基-2-丙基-1,3-丙二醇或其烷氧基化衍生物(下文称为C11二醇)。
Description
本发明涉及一种可通过单体化合物缩聚或加聚获得的聚合物,其中作为单体化合物伴随使用式I的2-(2-甲基丁基)-2-丙基-1,3-丙二醇或其烷氧基化衍生物(下文也统称为C11二醇):
需要二醇制备聚合物,例如聚酯或聚氨酯。例如EP-A 562 578描述了不同环己烷二醇如1,4-环己烷二甲醇或1,4-环己烷二乙醇在制备聚酯中的用途。
式II的2-戊基-2-丙基-1,3-丙二醇在制备聚酯中的用途由JP HEI03-161452已知。
原则上,期望改进聚合物在它们的各种用途中的性能。
在聚合物用作涂料组合物、粘合剂或密封剂中的粘结剂的情况下,粘度特别重要,不论它是熔体粘度(100%体系)还是溶液粘度(聚合物溶液)。对于薄膜成形应用而言,产生的涂层应该具有良好机械性能,例如冲击韧性和弹性,高抗划性和冲击强度,对水、溶剂、油脂、化学品和环境影响的高抗性,以及高光泽度。
本发明的目的为提供这种聚合物。
因此发现了开头定义的聚合物以及它们在涂料组合物、密封剂或粘合剂中作为粘结剂的用途。
C11二醇或C11二醇混合物
伴随其它单体化合物,使用式I的2-(2-甲基丁基)-2-丙基-1,3-丙二醇制备本发明聚合物:
在下文中,当提及式I的2-(2-甲基丁基)-2-丙基-1,3-丙二醇以及当提及下式II的2-戊基-2-丙基-1,3-丙二醇时,意义在于往往还应该包括烷氧基化衍生物。更具体为可用氧化乙烯或氧化丙烯或其混合物烷氧基化二醇;例如可用1-20个,更具体为1-10个烷氧基烷氧基化醇基。
在一个优选的实施方案中,两种二醇未烷氧基化。
除式I的2-(2-甲基丁基)-2-丙基-1,3-丙二醇外,优选使用它与式II的2-戊基-2-丙基-1,3-丙二醇的混合物作为单体化合物制备本发明聚合物:
式I的2-(2-甲基丁基)-2-丙基-1,3-丙二醇下文也称为C11二醇;2-(2-甲基丁基)-2-丙基-1,3-丙二醇和2-戊基-2-丙基-1,3-丙二醇下文也称为C11二醇混合物。
C11二醇混合物例如可包含如下组分:
1-99重量%,更具体为5-95重量%2-(2-甲基丁基)-2-丙基-1,3-丙二醇,和
1-99重量%,更具体为5-95重量%2-戊基-2-丙基-1,3-丙二醇,
重量百分数基于所述二醇的总重量。
C11二醇混合物优选包含如下组分:
1-50重量%,更具体为2-30重量%,更优选5-20重量%,非常优选7-15重量%2-(2-甲基丁基)-2-丙基-1,3-丙二醇,和相应地
50-99重量%,更具体为70-98重量%,更优选80-95重量%,非常优选85-93重量%2-戊基-2-丙基-1,3-丙二醇,
重量百分数基于所述二醇的总重量。
特别合适的C11二醇混合物包含重量比为约8-12∶1的2-戊基-2-丙基-1,3-丙二醇和2-(2-甲基丁基)-2-丙基-1,3-丙二醇,即与2-(2-甲基丁基)-2-丙基-1,3-丙二醇相比,8-12倍,更具体为约10倍量的2-戊基-2-丙基-1,3-丙二醇。
C11二醇混合物可包含其它组分;以上重量仅意欲用来限定两种二醇相互重量比。
C11二醇或C11二醇混合物的制备
可通过现有技术方法制备2-戊基-2-丙基-1,3-丙二醇和/或2-(2-甲基丁基)-2-丙基-1,3-丙二醇。
在C11二醇混合物的情况下,两种二醇例如可分别合成,然后以所需比例混合或未预先混合独立使用制备聚合物;在C11二醇混合物的情况下,重要的是聚合物包含相应量的两种二醇。
C11二醇混合物优选预先作为混合物制备并且用作制备聚合物的混合物。
下述为C11二醇混合物的一种优选合成途径。从C11二醇混合物中可以分离所需二醇,如果需要的话从而获得纯2-戊基-2-丙基-1,3-丙二醇和/或2-(2-甲基丁基)-2-丙基-1,3-丙二醇或制备这两种二醇的任意所需混合物。
WO 03/018192描述了制备包含2-丙基庚烯醛和2-丙基-4-甲基己烯醛(例如约10∶1的量)的C10混合物(所要求保护方法的步骤a)-c))。丁烯的加氢甲酰基化得到戊醛(正戊醛)和较少量2-甲基丁醛的混合物。随后醛醇缩合并消除水生成2-丙基庚烯醛和2-丙基-4-甲基己烯醛的混合物。
可在第一工艺步骤中将所得2-丙基庚烯醛和2-丙基-4-甲基己烯醛的混合物氢化成相应链烷醛(2-丙基庚醛和2-丙基-4-甲基己醛)。可用通常方法进行氢化。合适的氢化方法例如描述在DE-A 19524971中。
优选使用常规氢化催化剂,例如钯/Al2O3催化氢化。
对于氢化,例如还可使用镍、铜、铜/镍、铜/铬、铜/铬/镍、锌/铬和镍/钼催化剂。例如催化剂可为无载体的,或可将活性氢化物质和/或它们的前体应用于载体如SiO2或Al2O3上。氢化优选以液相氢化进行。氢化可在1-100巴的压力下进行。反应温度优选为50-200℃,优选80-150℃。
氢化后获得的2-丙基庚醛和2-丙基-4-甲基己醛的混合物可通过交叉坎尼扎罗反应(使用两种不同醛的坎尼扎罗反应;在这种情况下醛1:上述混合物,醛2:甲醛)而反应。这种交叉坎尼扎罗反应的实施为本领域技术人员所熟知并且例如描述在JP-HEI 03-161452中。作为催化剂优选使用碱金属氢氧化物(例如NaOH、Ca(OH)2、KOH)。交叉坎尼扎罗反应伴随甲酸生成,其生成作为盐(例如甲酸钠或甲酸钾)并且可容易分离。
代替交叉坎尼扎罗反应的另一种合成途径例如为2-丙基庚烯醛和2-丙基-4-甲基己烯醛与甲醛的醛醇缩合反应并随后氢化成C11二醇混合物,如WO 04/092097中所述。
以上方法中的所有步骤可不连续或优选连续进行。
特别优选可通过上述方法获得C11二醇混合物,即通过如下步骤:
a)将丁烯加氢甲酰基化成戊醛和2-甲基丁醛,
b)随后进行醛醇缩合反应同时消除水形成2-丙基庚烯醛和2-丙基-4-甲基己烯醛,
c)随后氢化成2-丙基庚醛和2-丙基-4-甲基己醛,以及
d)2-丙基庚醛和2-丙基-4-甲基己醛与甲醛进行交叉坎尼扎罗反应,或2-丙基庚烯醛和2-丙基-4甲基己烯醛与甲醛进行醛醇缩合反应并随后氢化。
如果需要的话,所得C11二醇混合物还可包含其它组分,更具体为其它二醇或醛。
所得C11二醇混合物通常由至少90重量%的式I和II两种二醇构成。
从所得混合物中可通过蒸馏分离各二醇或改变和调整各二醇的浓度。
如果需要烷氧基化二醇,可随后用氧化烯如氧化乙烯或氧化丙烯进行羟基的烷氧基化。
聚合物
聚合物可通过伴随使用C11二醇或C11二醇混合物由单体化合物缩聚或加聚获得;如果需要的话,可通过其它或进一步反应化学改性聚合物-例如官能化或交联。
单体化合物的缩聚使水或醇消除;加聚未产生任何消除。
优选缩聚物为聚酯,其可通过二醇或多元醇与二羧酸或多元羧酸反应获得,其还可以反应性衍生物,例如酸酐或酯的形式使用。
术语“聚酯”在下文意指由大于50重量%,更优选大于70重量%,更具体为大于90重量%选自二醇、多元醇、二羧酸和多元羧酸的合成组分构成的聚合物。
还可提及聚碳酸酯二醇,其可通过使碳酸二烷基酯与二醇反应同时消除醇获得。
可提及的特殊加聚物为聚氨酯。同样合适的例如为可通过内酯或内酰胺的开环聚合获得的加聚物。
术语“聚氨酯”在下文意指由大于50重量%,更优选大于70重量%,更具体为大于90重量%选自二异氰酸酯、多异氰酸酯、二醇和多元醇的合成组分构成的聚合物。
所有这些聚合物的共同特征为它们主要由二醇和对这些二醇呈反应性的化合物如二-和/或多元羧酸(聚酯)或二-和/或多异氰酸酯(聚氨酯)合成。
优选聚合物为聚酯和聚氨酯,特别优选为聚酯。
本发明的聚合物优选具有如下所示含量的C11二醇或C11二醇混合物;如下关于C11二醇或C11二醇混合物在聚合物中量的重量值与衍生自C11二醇或C11二醇混合物的聚合物单元有关。在加聚物的情况下,这些单元的重量对应C11二醇或C11二醇混合物无变化;在缩聚物的情况下,这些单元的重量减少了羟基的氢原子。
优选聚合物由至少0.5重量%,更优选至少2重量%,非常优选至少5重量%,更具体为至少10重量%,且在一个特殊实施方案中至少为20重量%C11二醇或C11二醇混合物构成。因为必须伴随使用对二醇呈反应性的其它化合物,聚合物通常由不超过70重量%,更具体为不超过60重量%或不超过50重量%C11二醇或C11二醇混合物构成。
除C11二醇或C11二醇混合物外,聚合物还可包含其它二醇或多元醇作为合成组分。在一个优选的实施方案中,其中构成聚合物的至少10重量%,更优选至少25重量%,非常优选至少50重量%二醇和多元醇为C11二醇或C11二醇混合物。
更具体而言,其中构成聚合物的至少70重量%或至少90重量%二醇和多元醇可为C11二醇或C11二醇混合物。
在一个特殊实施方案中,其中构成聚合物的100重量%所有二醇和多元醇为C11二醇或C11二醇混合物。
聚酯的其它组分
除C11二醇或C11二醇混合物外,聚酯可包含其它二醇或多元醇作为合成组分。
二醇的实例包括乙二醇、丙二醇和它们更高缩聚的对应物,例如二甘醇、三甘醇、二丙二醇、三丙二醇等,例如丁二醇、戊二醇、己二醇、新戊二醇、烷氧基化酚类化合物,例如乙氧基化和/或丙氧基化双酚类,和环己烷二甲醇;适合作为其它合成组分的多元醇为三官能和高级多官能醇,例如甘油、三羟甲基丙烷、丁三醇、三羟甲基乙烷、季戊四醇、新戊二醇、双三羟甲基丙烷、二季戊四醇、山梨醇和甘露糖醇。
以上二醇或多元醇可被烷氧基化,更具体而言乙氧基化和丙氧基化。烷氧基化产物可以通过使上述醇与氧化烯,更尤其是氧化乙烯或氧化丙烯反应的已知方法获得。每个羟基的烷氧基化度优选为0-10,即1mol的羟基可优选被至多10mol的氧化烯烷氧基化。
聚酯进一步包含二羧酸或多元羧酸作为合成组分。在制备聚酯中,二羧酸或多元羧酸例如还可以它们的反应性衍生物,例如酸酐或酯的形式使用。合适的二羧酸为琥珀酸、戊二酸、己二酸、癸二酸、间苯二甲酸、对苯二甲酸、它们的异构体和氢化产物,例如四氢化邻苯二甲酸。同样适合的为用于不饱和聚酯的马来酸和富马酸。
聚酯还可包含一元醇或一元羧酸作为组分;使用这种化合物作为伴随物允许调节和/或限制分子量。
为了获得特殊性能,聚酯可包含特殊官能团。为了获得在水中的溶解性或在水中的分散性,水溶性或水分散性聚酯例如包含一定量的亲水基团、羧基或羧酸酯基团。用于粉末涂料的可交联聚酯例如包含参与与所用交联剂交联反应的官能团。如果意欲与含羟基化合物,羟烷基酰胺交联,则这些例如还可为羧酸基团。官能团还可为烯属不饱和基团,因此例如用不饱和二羧酸(马来酸)改性聚酯或与(甲基)丙烯酸反应;这种聚酯可辐射固化。
不饱和聚酯例如还可与单烯属不饱和或多烯属不饱和、可自由基聚合的化合物如苯乙烯、丙烯酸C1-C10烷基酯、丙烯酸二烷基酯如乙二醇或丁二醇的二丙烯酸酯共聚。如WO 00/23495和EP 1131372中所述,不饱和聚酯为此例如可以与烯属不饱和单体的混合物使用。在这种情况下,上述烯属不饱和化合物同时用作溶剂(活性稀释剂),因此混合物优选作为聚酯在这些化合物中的溶液存在。例如混合物可用作涂料或浸渍组合物,尤其是用于层压材料的制备。可进行热或光化学固化,在两种情况下如果需要的话加入引发剂。
聚氨酯的其它组分
聚氨酯包含二-或多异氰酸酯作为主要合成组分。
尤其包含二异氰酸酯X(NCO)2,其中X为具有4-15个碳原子的脂族烃基、具有6-15个碳原子的脂环族或芳族烃基或具有7-15个碳原子的芳脂族烃基。这种二异氰酸酯的实例为四亚甲基二异氰酸酯、六亚甲基二异氰酸酯、十二亚甲基二异氰酸酯、1,4-二异氰酸酯基环己烷、1-异氰酸酯基-3,5,5-三甲基-5-异氰酸酯基甲基环己烷(IPDI)、2,2-双(4-异氰酸酯基环己基)丙烷、三甲基己烷二异氰酸酯、1,4-二异氰酸酯基苯、2,4-二异氰酸酯基甲苯、2,6-二异氰酸酯基甲苯、4,4′-二异氰酸酯基二苯甲烷、2,4′-二异氰酸酯基二苯甲烷、对苯二亚甲基二异氰酸酯、四甲基苯二亚甲基二异氰酸酯(TMXDI)、双(4-异氰酸酯基环己基)甲烷(HMDI)异构体,例如反式/反式、顺式/顺式、和顺式/反式异构体,以及这些化合物的混合物。
这种二异氰酸酯可商购。
这些异氰酸酯的特别重要混合物为二异氰酸酯基甲苯和二异氰酸酯基二苯甲烷的各自结构异构体的混合物,特别合适为80摩尔%的2,4-二异氰酸酯基甲苯和20摩尔%的2,6-二异氰酸酯基甲苯的混合物。同样有利的尤其为芳族异氰酸酯如2,4-二异氰酸酯基甲苯和/或2,6-二异氰酸酯基甲苯与脂族或脂环族异氰酸酯如六亚甲基二异氰酸酯或IPDI的混合物,脂族对芳族异氰酸酯的优选混合比为4∶1-1∶4。
作为与二-或多异氰酸酯反应的二醇和/或多元醇,本发明单独使用C11二醇或以与其它二醇或多元醇的混合物使用C11二醇。
在聚氨酯的情况下,所用二醇优选包括聚酯醇,尤其是聚酯二醇。这种聚酯醇预先通过使二醇或多元醇与二羧酸或多元羧酸反应获得(参见以上聚酯的说明)。C11二醇可在聚氨酯中以这种聚酯醇的形式存在。其它二醇和多元醇包括以上确定的那些,无论作为直接与二-或多异氰酸酯反应的合成组分,还是作为聚酯二醇的组分。用于聚酯二醇的合适的二羧酸或多元羧酸也为以上确定的那些。
聚氨酯还可包含单醇或单异氰酸酯组分;可通过伴随使用这种化合物调节或限制分子量。
为了获得特殊性能,聚氨酯可包含特殊官能团。为了获得在水中的溶解性或分散性,水溶性或水分散性聚氨酯例如包含一定量的亲水基团,羧基或羧酸酯基团。合适的合成组分的实例为二羟甲基丙酸。可交联的聚氨酯包含参与与所用交联剂交联反应的官能团。除氨基甲酸酯基团外,聚氨酯尤其还可以包含其它官能团,例如通过二-或多异氰酸酯与氨基化合物反应产生的脲基。
如果需要的话,聚合物例如可通过其它或进一步反应,例如官能化或交联,在当时,或尤其是随后任意时间点,例如在使用期间化学改性。
聚合物更尤其可包含交联基团,一旦存在一定条件,所述交联基团参与交联反应。聚合物尤其还可以与交联剂的混合物使用,所需交联剂在所需时间点在一定条件下(更具体为升温下)参与与聚合物的交联反应。
根据交联剂的反应性,把单组分(1C)和双组分(2C)体系区分开。在2C体系中,直到在后续使用前不久才加入交联剂;在1C体系的情况下,可以在初始阶段将交联剂加入体系中(潜伏性交联剂),并且交联仅在随后设置条件的情况下进行,例如当除去溶剂和/或升温时。
常规交联剂的实例包括异氰酸酯、环氧化物、酸酐、或在具有自由基聚合性烯属不饱和基团的聚合物情况下,烯属不饱和单体如苯乙烯。
聚合物的用途
聚合物适合作为热塑性组合物的组分。为此,聚合物,例如聚酯或聚氨酯,优选具有足够高的分子量以赋予它们热塑性。
热塑性组合物通常用于生产模制品,在这种情况下可采用常规方法如注塑、挤出或吹塑。
聚合物尤其适合作为涂料组合物、密封剂或粘合剂的组分。
涂料组合物、密封剂或粘合剂优选包含本发明聚合物作为粘结剂。它们可包含其它粘结剂和其它添加剂,实例为抗氧化剂、稳定剂、染料、颜料、流动控制助剂、增稠剂或润湿助剂。
涂料组合物、密封剂或粘合剂可为含水或溶剂型组合物。优选为含水组合物。
这种组合物优选以在水或有机溶剂或其混合物中的溶液或分散体形式包含本发明粘结剂。必要时,聚合物包含带来在水或有机溶剂中,优选在水中的溶解性或分散性的其它官能团(参见上文)。
涂料组合物、密封剂或粘合剂还可为基本无水或有机溶剂的组合物(并且称为100%体系)。这种组合物通常每100重量份组合物包含小于10重量份的水或其它有机溶剂(沸点在1巴下低于150℃)。特别优选每100重量份的组合物包含小于两重量份,非常特别优选小于1重量份,或小于0.5重量份的水或其它有机溶剂(沸点在1巴下低于150℃)。
所述组合物例如可为在室温下仍为流体或可为粉末状的组合物,其仅在高温下加工。
组合物,更具体为涂料组合物,可为可辐射固化的和/或可用作可辐射固化组合物或涂料组合物。为此它们优选包含本发明的可辐射固化聚合物,更具体为可辐射固化聚酯(参见上文)。可用高能辐射进行辐射固化,例如电子束或UV光;当使用UV光时,可优选将光引发剂加入聚合物中。
在本发明上下文中的一种优选用途为本发明聚合物作为或在粉末涂料中的用途。优选使用聚酯作为可交联的粉末涂料。
在一个优选的实施方案中,粉末涂料例如通过将聚酯、交联剂和其它添加剂,颜料和流动调节剂在高温下混合并且熔融制备。可通过后续挤出以及挤出物的相应加工将混合物变成粉末形式。
可将粉末涂料以常规方法,例如包括静电施用于所需基材上,实例为具有金属、塑料或木材表面的那些。
本发明聚合物具有低粘度、以及低熔体粘度(100%体系)或低溶液粘度(聚合物溶液)。低粘度易于处理,导致良好的涂层性能,并且容许在溶液或分散体中更高的固含量,或在颜料组合物中更低的粘结剂比例。本发明聚合物尤其还非常耐水解。
在涂料组合物、密封剂和粘合剂的应用领域中,本发明聚合物产生良好机械性能;尤其是,涂料组合物,例如粉末涂料具有高冲击韧性、良好弹性和良好光泽度。
实施例
C11二醇混合物的制备
2-丙基庚烯醛:2-丙基-4-甲基己烯醛的选择性氢化:
起始溶液为包含2-丙基庚烯醛和2-丙基-4-甲基己烯醛(~10∶1)的异构体混合物,如WO 2003018192A1中所述,其由C5醛异构体混合物制备。
在40巴的H2压力下,在加热至150℃的反应器(14l固定床反应器,直径为70mm)中以喷淋模式将混合物作为原料进行氢化(混合物包含91重量%的C10醛)。空间速度为0.1kg有机物/I催化剂*h。将部分氢化排出物重新混入原料中(循环模式)。对原料的循环比为10∶1。将1.3kg/h原料和500Nl/h新鲜气体注入反应器中。排出物包含10.7%2-丙基-4-甲基己醛,78.7%2-丙基庚醛和2%C10醇。
交叉坎尼扎罗反应
向具有冷却回流冷凝器、贮液器、低温恒温器和KPG搅拌器的5000mlHWS反应烧瓶中装入865g 2-丙基庚醛和2-丙基-4-甲基己醛的混合物(混合物包含87%C10饱和醛)、1500g甲醛(在水中30%浓度)和238g甲醇。在3小时的时间内,在50℃下,使用HPLC泵逐滴加入1273g 25%浓度NaOH。在55℃下搅拌配料另外1h。冷却至室温后,用甲酸调节PH。分离相并且有机相无低沸物(20毫巴和85℃)然后通过填料塔(长250mm,直径40mm)在减压下蒸镏。获得780g(83%收率)混合物(~10∶1,96%,2-丙基-2-(2-甲基丁基)-1,3-丙二醇(93%)和2-丙基-2-戊基-1,3-丙二醇(5.8%))。在1毫巴的压力下,在128-132℃(液相温度152-165℃)的顶部温度下,获得主要馏分。借助GC、GC-MS和NMR(1H,13C)测定二醇结构。
主要异构体在13C NMR中的化学位移(DMSO):2-丙基-2-戊基-1,3-丙二醇δ(ppm)=64.1(2×CH2OH),21.9(C5),22.2(C7),32.5(C9),14.9(C11),41.1(C1),30.4(C4),33.0(C6),13.83(C8),15.6(C10);2-丙基-2-(2-甲基丁基)-1,3-丙二醇δ(ppm)=69.5(2×CH2OH),29.2(C5),11.3(C7),29.7(C9),14.9(C11),36.9(C1),45.1(C4),31.0(C6),22.0(C8),15.6(C10)。
2-丙基-2-(2-甲基丁基)-1,3-丙二醇和2-丙基-2-戊基-1,3-丙二醇的~50∶50混合物的制备
将C11二醇混合物(10∶902-丙基-2-(2-甲基丁基)-1,3-丙二醇和2-丙基-2-戊基-1,3-丙二醇)在填料塔(长为2m)中蒸馏。在1毫巴的压力和120-122℃的顶部温度(液相温度为172-178℃)下,获得50∶50的二醇混合物。借助GC和NMR测定二醇的比率。
纯2-丙基-2-戊基-1,3-丙二醇(纯度96GC面积%)的制备
通过在填料塔(长为2m)上蒸镏C11二醇混合物(~10∶902-丙基-2-(2-甲基丁基)-1,3-丙二醇和2-丙基-2-戊基-1,3-丙二醇)的主要馏分获得二醇。在1毫巴的压力和123℃(175-81℃)的顶部温度下获得纯2-丙基-2-戊基-1,3-丙二醇。借助GC和NMR测定纯度和结构。
用途实施例
实施例
缩写
ADA:己二酸
D:多分散性指数(Mw/Mn)
DPG:二丙二醇
DBTO:二丁基氧化锡
DSC:差示扫描量热法
GPC:凝胶渗透色谱法
IPA:间苯二甲酸
Mn:数均分子量[g/mol]
Mw:重均分子量[g/mol]
NVC:非挥发物含量
NPG:新戊二醇
OHN:OH值
C11二醇混合物:重量比为10∶1的2-戊基-2-丙基-1,3-丙二醇和2-(2-甲基丁基)-2-丙基-1,3-丙二醇(以上式I和II)的混合物
PPPD:2-戊基-2-丙基-1,2-丙二醇
AN:酸值
Tg:玻璃化转变温度
TMP:三羟甲基丙烷
TMAA:偏苯三酸酐
TPA:对苯二甲酸
η1:熔体粘度
η2:溶液粘度
聚合物表征方法
分子量测定通过GPC进行。固定相:高度交联的多孔聚苯乙烯-二乙烯基苯,可从Polymer Laboratories作为PL-GEL商购。流动相:THF。流速:0.3ml/min。用来自PSS的28700-194道尔顿的聚乙二醇校准。
聚酯的酸值通过DIN标准方法53169测定。使用锥/板粘度计在160℃下以振动模式且在0.1rad/s的角速度下测定聚酯的熔体粘度η1。使用锥/板粘度计在室温下以旋转模式测定聚酯的溶液粘度η2。溶液由70%聚酯和30%溶剂(Solvesso 100TM/Solvenon PMTM的5/1混合物)构成。
根据ASTM D3418借助DSC测定聚酯的Tg。
具有COOH基团的粉末聚酯的制备
聚酯P1
步骤I-含OH低聚物的制备
将149.1g C11二醇混合物(0.80mol)、266.7g NPG(2.56mol)、53.7gTMP(0.4mol)、532.1g TPA(3.21mol)和0.7g DBTO催化剂装入配备温度计、惰性气体入口、搅拌器和回流冷凝器的2L四颈烧瓶中。在氮气流通过及回流下,将反应物混合物快速加热至180℃。将水连续蒸出。随后在搅拌和氮气流动下,将反应混合物在3-5小时内逐步加热至230℃,并且在230℃下进一步搅拌直到低聚物的AN为10-15mg KOH/g。低聚物的AN为10mg KOH/g。
步骤II-含COOH的聚合物P1的制备
将以上合成的低聚物冷却至180℃,然后加入133.0g IPA(0.80mol)。将温度升至230℃,并且在这些条件下继续缩合直到聚合物的AN为30-40mgKOH/g。为了得到所需AN,可在反应结束时通过温和真空脱去由聚合产生的水。产物为支化的含COOH粉末聚酯P1,其AN为30mg KOH/g。P1的玻璃化转变温度Tg为66℃且熔体粘度η1在160℃下为327Pa.s。GPC分析给出如下值:Mn=2980g/mol;D=19.4(参见表1)。
聚酯P2-P7
用概括在表1中的组合物,重复制备P1的程序。产物为支化的含COOH粉末聚酯,其主要AN、Mn、D、Tg和η1数据列在表1中。
P2用于对比
P3
P4
P5用于对比
P6
P7用于对比
表1
本发明聚合物P1、P3和P6具有比相应的对比聚合物P2、P5和P7显著更低的熔体粘度。
对比例聚酯P8
用概括在表2中的组合物,进行与制备P1相同的程序,聚酯不包含C11二醇混合物,而用线性PPPD代替。
表2
本发明包含C11二醇混合物的聚合物P3(表1)具有比相应含PPPD的对比聚合物P8更低的熔体粘度。
具有OH基团的无定形聚酯的制备
聚酯P9
将209.25g C11二醇混合物(1.11mol)、182.98g NPG(1.76mol)、148.59gTMP(1.11mol)、429.50g IPA(2.59mol)、161.90g ADA(1.11mol)和0.5g DBTO催化剂装入配备温度计、惰性气体入口、搅拌器和回流冷凝器的2L四颈烧瓶中。在氮气流通过及回流下,将反应物的混合物快速加热至160℃。将水连续蒸出。随后在搅拌和氮气流动下,将反应混合物在3-5小时内逐步加热至230℃,并且在230℃下进一步搅拌直到聚酯P8的AN为10-15mg KOH/g。产物为支化无定形的含OH聚酯P8,其AN为14mg KOH/g。P8的OHN为82mg KOH/g以及玻璃化转变温度Tg为19℃。GPC分析给出如下值:Mn=2000g/mol;D=5.3。P8的熔体粘度η1在160℃下为1.3Pa.s。聚酯P8在室温下的溶液粘度η2(具有70%的NVC和Solvesso 100TM/Solvenon PMTM的5/1混合物作为溶剂的P8溶液)为12.1Pa.s(参见表3)。
聚酯P10(用于对比)
用概括在表3中的组合物,进行与制备P9相同的程序。聚酯P10的主要数据列在表3中。
表3
本发明聚合物P9具有比对比聚合物P10显著更低的熔体粘度和显著更低的溶液粘度。
水可稀释性聚酯的制备
聚酯P11
步骤I-含OH低聚物的制备
将242.8g C11二醇混合物(1.29mol)、302.2g NPG(2.91mol)、401.9gIPA(2.42mol)和0.5g DBTO催化剂装入配备温度计、惰性气体入口、搅拌器和回流冷凝器的2L四颈烧瓶中。在氮气流通入及回流下,将反应物的混合物快速加热至160℃。将水连续蒸出。随后在搅拌和氮气流动下,将反应混合物在3-5小时内逐步加热至220℃,并且在220℃进一步搅拌直到反应混合物的AN为10-15mg KOH/g。低聚物的AN为15mg KOH/g。
步骤II-聚合物P11的制备
将以上合成的低聚物冷却至160℃,然后加入155.0g TMAA(0.81mol)。将温度升至230℃,并且在这些条件下继续缩合直到聚合物的AN为42-48mg KOH/g。为了得到所需AN,可在反应结束时通过温和真空脱去由聚合产生的水。产物为线性的水可稀释性聚酯P11,其AN为46mg KOH/g。P11的玻璃化转变温度Tg为41℃且熔体粘度η1在160℃下为1.4Pa.s。GPC分析给出如下值:Mn=1200g/mol;D=1.9(参见表4)。
P11的耐水解性评价
使用N,N-二甲基乙醇胺制备20%浓度的P11水胶溶液,调节pH为8,并且在45℃下储存。将直到胶体溶液沉淀时所花费的时间间隔作为聚酯耐水解性的测量标准(参见表5)。
聚酯P12(用于对比)
用概括在表4中的组合物,进行与制备P11相同的程序。聚酯P12的主要数据列在表4中。
表4
本发明聚合物P11具有比对比聚合物P12显著更低的熔体粘度。
表5
聚酯 | 水溶液沉淀的时间(天) |
P11 | >30天 |
P12 | 17天 |
本发明聚合物P11比对比聚合物P12明显更耐水解。
粉末涂料的制备
将来自DSMResins B.V的聚酯树脂P-862(Tg 58.0℃,AN 35mgKOH/g)用作参比粘结剂(REF)。粉末涂料PL3、PL4、PL5和PLR通过如下制备:将570.0g粉末聚酯P3、P4、P5(用于对比)或REF在每种情况下与30.0g商购固化剂XL-552(来自DSM的羟烷基酰胺)、300.0g二氧化钛颜料2160(来自Kronos)、9.0g流动调节剂PV5(来自WorléeChemiegmbH)和2.5g脱气剂苯偶姻在通用实验室混合机(MITMischtechnikgmbH)中相应地混合,熔融混合物并且随后在80-100℃下由双螺杆挤出机(MP19,APV)挤出熔体。然后粗糙压碎所得挤出物、研磨以及筛选。所得粉末涂料PL3、PL4和PL5进行如下测试:
此后将粉末涂料静电施用至在160℃下烘干10分钟的钢测试板(Q-板R-36)上。目标为获得涂层厚度为60μm-80μm。所得涂层进行如下测试:
涂层测试结果概括在表6中。
表6
*2=桔皮、针孔
**1=桔皮、个别针孔
本发明的粉末涂料具有良好的外形特征。PL3和PL4具有更好的光泽度,并且PL4具有比PL5更好的机械性能。
高固体1-组分(1K)涂料的制备
为了制备高固体1K涂料1K-PL9和1K-PL10,从而制备聚酯P9和P10在乙酸丁酯中的70%浓度溶液。将80g各自的70%浓度聚酯溶液与14g商购固化剂066(来自BASF的三聚氰胺缩合物)、4g正丁醇和2g对甲苯磺酸催化剂混合。使用四向棒状施涂器将所得溶液(NVC 70%)施用于玻璃板和钢测试板上。目标薄膜厚度为40-50μm。随后在140℃下将涂布测试板烘干30分钟。使所得涂料进行如下测试:
涂层测试的结果概括在表7中。
1K-PL9(基于聚酯P9)为本发明,而1K-PL10(基于聚酯P10)用作对比例。
表7
本发明的高固体涂料1K-PL9显示良好的外形特征。C11二醇混合物尤其是在膜弹性,以及耐酸性方面显示超过NPG的优点。
高固体2-组分(2k)涂料的制备
为了制备高固体2K涂料2K-PL9和2K-PL0,从而制备聚酯P9和P10在乙酸丁酯中的70%浓度溶液。将70g各自的70%浓度聚酯溶液与1g流动调节剂OL17(来自BorchersgmbH的聚醚)的溶液(10%浓度,在乙酸丁酯中)、1g二月桂酸二丁锡溶液(5%浓度,在乙酸丁酯中)作为催化剂、3g甲氧基丙基乙酸酯、20g商购固化剂HI190BS(90%形式,来自BASF的多异氰酸酯)和5g乙酸丁酯混合。使用四向棒状施涂器将所得溶液(NVC 67%)施用于玻璃板和钢测试板上。目标薄膜厚度为40-50μm。随后在80℃下将涂布测试板烘干30分钟。使所得涂层进行如下测试:
涂层测试的结果概括在表8中。
2K-PL9(基于聚酯P9)为本发明,而2K-PL10(基于聚酯P10)用作对比例。
表8
本发明的高固体涂料2K-PL9显示良好的外形特征。机械性能比基于NPG涂料2K-PL10显著更好。
Claims (18)
1.一种可通过单体化合物缩聚或加聚获得的聚合物,其中作为单体化合物伴随使用式I的2-(2-甲基丁基)-2-丙基-1,3-丙二醇或其烷氧基化衍生物(下文也统称为C11二醇):
3.根据权利要求2的聚合物,其中所述C11二醇混合物由如下组分构成:
1-99重量%2-(2-甲基丁基)-2-丙基-1,3-丙二醇或其烷氧基化衍生物,和
1-99重量%2-戊基-2-丙基-1,3-丙二醇或其烷氧基化衍生物。
4.根据权利要求2或3的聚合物,其中所述C11二醇混合物可通过如下步骤获得:
a)将丁烯加氢甲酰基化成戊醛和2-甲基丁醛,
b)随后进行醛醇缩合反应同时消除水形成2-丙基庚烯醛和2-丙基-4-甲基己烯醛,
c)随后氢化成2-丙基庚醛和2-丙基-4-甲基己醛,以及
d)2-丙基庚醛和2-丙基-4-甲基己醛与甲醛进行交叉坎尼扎罗反应,或2-丙基庚烯醛和2-丙基-4-甲基己烯醛与甲醛进行醛醇缩合反应并随后氢化。
5.根据权利要求1-4中任一项的聚合物,其中所述聚合物由0.5-70重量%2-(2-甲基丁基)-2-丙基-1,3-丙二醇、其烷氧基化衍生物(C11二醇)或C11二醇混合物构成。
6.根据权利要求1-5中任一项的聚合物,其为聚酯。
7.根据权利要求1-5中任一项的聚合物,其为聚碳酸酯二醇(可通过使碳酸二烷基酯与二醇反应同时消除醇获得)。
8.根据权利要求1-5中任一项的聚合物,其为聚氨酯。
9.根据权利要求1-5中任一项的聚合物,其为可通过内酯或内酰胺的开环聚合获得的加聚物。
10.一种包含根据权利要求1-9中任一项的聚合物的热塑性组合物。
11.根据权利要求10的热塑性组合物在生产模制品中的用途。
12.一种包含根据权利要求1-9中任一项的聚合物的涂料组合物、密封剂或粘合剂。
13.根据权利要求12的涂料组合物、密封剂或粘合剂,其为含水组合物。
14.一种包含根据权利要求1-9中任一项的聚合物的粉末涂料。
15.一种包含根据权利要求1-9中任一项的聚合物的可辐射固化涂料组合物。
16.一种由2-(2-甲基丁基)-2-丙基-1,3-丙二醇或其烷氧基化衍生物与2-戊基-2-丙基-1,3-丙二醇或其烷氧基化衍生物构成的二醇混合物。
18.一种由如下组分构成的二醇混合物:
1-99重量%2-(2-甲基丁基)-2-丙基-1,3-丙二醇或其烷氧基化衍生物,和
1-99重量%2-戊基-2-丙基-1,3-丙二醇或其烷氧基化衍生物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP08158308.0 | 2008-06-16 | ||
EP08158308 | 2008-06-16 | ||
PCT/EP2009/057133 WO2009153193A1 (de) | 2008-06-16 | 2009-06-10 | Verwendung eines c11-diols oder c11-diolgemisches zur herstellung von polymeren |
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CN102066457A true CN102066457A (zh) | 2011-05-18 |
CN102066457B CN102066457B (zh) | 2013-04-17 |
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CN2009801227626A Expired - Fee Related CN102066457B (zh) | 2008-06-16 | 2009-06-10 | C11二醇或c11二醇混合物在生产聚合物中的用途 |
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US (1) | US8519084B2 (zh) |
EP (1) | EP2291432B1 (zh) |
JP (1) | JP2011524451A (zh) |
KR (1) | KR20110040838A (zh) |
CN (1) | CN102066457B (zh) |
ES (1) | ES2391072T3 (zh) |
WO (1) | WO2009153193A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109153624A (zh) * | 2016-05-12 | 2019-01-04 | 佩什托普公司 | 用于生产混合的2,2-二烷基-1,3-丙二醇的方法 |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2470156A2 (de) * | 2009-08-26 | 2012-07-04 | Basf Se | Verwendung von 1,3-diolen als biozide |
US9394212B2 (en) | 2010-06-15 | 2016-07-19 | Basf Se | Process for the cooligomerization of olefins |
DE102011080722A1 (de) | 2010-08-12 | 2012-03-22 | Basf Se | Verwendung von Methylbernsteinsäure in Pulverlacken |
BR112013018345B1 (pt) * | 2011-01-19 | 2019-02-26 | Dsm Ip Assets B.V. | Hidrogenação de ligação dupla carbono-carbono catalítica |
CN105102420B (zh) | 2013-03-28 | 2018-09-21 | 巴斯夫欧洲公司 | 基于1,3-二醇的聚醚胺 |
MX2015013670A (es) | 2013-03-28 | 2016-02-18 | Procter & Gamble | Composiciones de limpieza que contiene una polieteramina. |
CA2941253A1 (en) | 2014-03-27 | 2015-10-01 | Frank Hulskotter | Cleaning compositions containing a polyetheramine |
PL3122717T3 (pl) | 2014-03-27 | 2019-08-30 | Basf Se | Eteroaminy na bazie 1,2-dialkoholi |
WO2015148361A1 (en) | 2014-03-27 | 2015-10-01 | The Procter & Gamble Company | Cleaning compositions containing a polyetheramine |
PL3122716T3 (pl) | 2014-03-27 | 2019-06-28 | Basf Se | Eteroaminy oparte o dialkohole |
EP2940116B1 (en) | 2014-04-30 | 2018-10-17 | The Procter and Gamble Company | Detergent |
EP2940117B1 (en) | 2014-04-30 | 2020-08-19 | The Procter and Gamble Company | Cleaning composition containing a polyetheramine |
US9974985B2 (en) | 2014-05-15 | 2018-05-22 | Basf Se | Etheramines based on 1,2-dialcohols |
US9617502B2 (en) | 2014-09-15 | 2017-04-11 | The Procter & Gamble Company | Detergent compositions containing salts of polyetheramines and polymeric acid |
WO2016041697A1 (en) | 2014-09-15 | 2016-03-24 | Basf Se | Salts of etheramines and polymeric acid |
US9631163B2 (en) | 2014-09-25 | 2017-04-25 | The Procter & Gamble Company | Liquid laundry detergent composition |
EP3197988B1 (en) | 2014-09-25 | 2018-08-01 | The Procter & Gamble Company | Cleaning compositions containing a polyetheramine |
CA2959937A1 (en) | 2014-09-25 | 2016-03-31 | Basf Se | Polyetheramines based on 1,3-dialcohols |
JP6430632B2 (ja) | 2014-09-25 | 2018-11-28 | ザ プロクター アンド ギャンブル カンパニー | ポリエーテルアミンを含有する布地ケア組成物 |
ES2689048T3 (es) | 2015-10-29 | 2018-11-08 | The Procter & Gamble Company | Composición detergente líquida |
EP3162880A1 (en) | 2015-10-29 | 2017-05-03 | The Procter and Gamble Company | Liquid detergent composition |
US20170275565A1 (en) | 2016-03-24 | 2017-09-28 | The Procter & Gamble Company | Compositions containing an etheramine |
EP3257924A1 (en) | 2016-06-17 | 2017-12-20 | The Procter and Gamble Company | Liquid detergent composition |
EP3279301A1 (en) | 2016-08-04 | 2018-02-07 | The Procter & Gamble Company | Water-soluble unit dose article comprising a cleaning amine |
DE102018123339A1 (de) | 2018-09-21 | 2020-03-26 | Saertex Multicom Gmbh | Sanierung von Hochtemperaturleitungen |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5838717A (ja) * | 1981-09-01 | 1983-03-07 | Daicel Chem Ind Ltd | ポリウレタンの製造方法 |
JPH0627083B2 (ja) | 1989-11-21 | 1994-04-13 | チッソ株式会社 | プロパンジオールおよびその製造法 |
JPH04139212A (ja) * | 1990-09-28 | 1992-05-13 | Chisso Corp | 変性ポリエステル樹脂及びこれを用いた熱接着性複合繊維 |
JP3161452B2 (ja) | 1991-02-12 | 2001-04-25 | 富士ゼロックス株式会社 | 自動原稿搬送装置 |
JP3004762B2 (ja) * | 1991-04-08 | 2000-01-31 | チッソ株式会社 | 放射線硬化型樹脂組成物 |
CA2092248A1 (en) | 1992-03-24 | 1993-09-25 | Kenji Kushi | Polyester resin for a dye receptive layer of a recording medium for sublimation type heat-sensitive transfer recording process, and a recording medium using the polyester resin |
US5350830A (en) * | 1992-11-27 | 1994-09-27 | Eastman Chemical Company | Thermosetting coating compositions |
JP3232817B2 (ja) * | 1993-10-28 | 2001-11-26 | チッソ株式会社 | 低誘電性ポリエステル |
DE19524971A1 (de) | 1995-07-08 | 1997-01-09 | Huels Chemische Werke Ag | Verfahren zur katalytischen Selektivhydrierung von mehrfach ungesättigten organischen Substanzen |
JP4278191B2 (ja) * | 1996-05-15 | 2009-06-10 | Dic株式会社 | 水性ポリウレタン樹脂組成物及び接着剤 |
EP0962484B1 (en) * | 1998-05-18 | 2008-08-06 | Toyo Boseki Kabushiki Kaisha | Optical-use adhesive film |
FI982256A (fi) | 1998-10-19 | 2000-04-20 | Neste Oyj | Tyydyttymättömiä polyesterihartseja |
JP2000336140A (ja) * | 1999-05-26 | 2000-12-05 | Lion Corp | ポリウレタン用ポリカーボネートジオール |
KR100851101B1 (ko) * | 2001-03-29 | 2008-08-08 | 바스프 에스이 | Viii 아족 금속과의 니코겐 킬레이트 착물용 리간드및 히드로포르밀화, 카르보닐화, 히드로시안화 또는수소화 반응을 위한 촉매로서의 착물의 용도 |
AU2002324067A1 (en) | 2001-08-24 | 2003-03-10 | Basf Aktiengesellschaft | Method for the production of 2-propylheptanol and hydroformylating catalysts and the further use thereof for carbonylation, hydrocyanation and hydrogenation |
US6593419B2 (en) * | 2001-10-11 | 2003-07-15 | Dainippon Ink And Chemicals, Inc. | Polyurethane resin and method for producing the same, resin composition and sheet-form article |
DE10317543A1 (de) | 2003-04-16 | 2004-11-04 | Basf Ag | Verfahren zur Hydrierung von Methylolalkanalen |
EP1925983B1 (en) | 2006-11-22 | 2014-11-12 | Ricoh Company, Ltd. | Toner and developer |
-
2009
- 2009-06-10 JP JP2011513990A patent/JP2011524451A/ja not_active Ceased
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- 2009-06-10 KR KR1020117001023A patent/KR20110040838A/ko not_active Application Discontinuation
- 2009-06-10 CN CN2009801227626A patent/CN102066457B/zh not_active Expired - Fee Related
- 2009-06-10 EP EP09765773A patent/EP2291432B1/de not_active Not-in-force
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109153624A (zh) * | 2016-05-12 | 2019-01-04 | 佩什托普公司 | 用于生产混合的2,2-二烷基-1,3-丙二醇的方法 |
CN109153624B (zh) * | 2016-05-12 | 2022-11-29 | 佩什托普公司 | 用于生产混合的2,2-二烷基-1,3-丙二醇的方法 |
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JP2011524451A (ja) | 2011-09-01 |
US20110130514A1 (en) | 2011-06-02 |
EP2291432A1 (de) | 2011-03-09 |
WO2009153193A1 (de) | 2009-12-23 |
KR20110040838A (ko) | 2011-04-20 |
EP2291432B1 (de) | 2012-08-15 |
US8519084B2 (en) | 2013-08-27 |
CN102066457B (zh) | 2013-04-17 |
ES2391072T3 (es) | 2012-11-21 |
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