CN105934437B - 硅烷改性的甲酰胺 - Google Patents
硅烷改性的甲酰胺 Download PDFInfo
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- CN105934437B CN105934437B CN201580006602.0A CN201580006602A CN105934437B CN 105934437 B CN105934437 B CN 105934437B CN 201580006602 A CN201580006602 A CN 201580006602A CN 105934437 B CN105934437 B CN 105934437B
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- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
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- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
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Abstract
本发明涉及用于胶粘和/或密封各种基底材料,例如金属、木材、玻璃和/或塑料的新型的硅烷改性的甲酰胺聚合物和/或预聚物。另外提供包含根据本发明的硅烷改性甲酰胺聚合物的反应性单组分胶粘剂体系。
Description
本发明的技术领域
本发明涉及用于涂覆、胶粘和/或密封各种基底材料,例如金属、木材、玻璃和/或塑料的式(I)和式(IV)的新型的硅烷改性的甲酰胺预聚物。另外提供包含根据本发明的式(I)和/或式(IV)的硅烷改性甲酰胺预聚物的反应性单组分胶粘剂体系。
发明背景
硅烷改性的聚合物多年来已广为人知,并且基于硅烷改性预聚物或聚合物的密封剂或胶粘剂已证实成功用于非常广泛的用途,例如汽车构造、窗户或建筑立面中的接缝密封。
非常通常,硅烷改性聚合物(其在加工前为预聚物形式)被理解为是包含具有可水解基团的硅烷基团的聚合物且其聚合物骨架不是像硅酮那样基本由O-Si-O-Si链构成而是由在大多数情况下被杂原子中断并进一步包含氨基甲酸酯、醚、酯、脲、酰胺和其它结构单元的C-C链构成。在水分的作用下,硅烷基团上的基团——例如通常乙酸酯基团或烷氧基——水解以形成反应性硅烷醇,其随后缩合并固化并裂解出水、醇或乙酸,以形成高分子量网络。
这些硅烷改性聚合物的价值主要是它们的特定性质状况。这是因为,一方面,包含硅烷改性聚合物的涂料、胶粘剂或密封剂以在没有复杂预处理(不需要底漆)下与非常多样化的基底的强粘附力为特征。这是因为在无机基底表面上通常存在OH基团,其能与在水分作用下形成的该聚合物的反应性硅烷醇反应。另一方面,可借助聚合物骨架使该硅烷改性聚合物的性质适应大量极为不同的用途。
目前市场上可购得的硅烷改性聚氨酯和聚脲因此基于如下列图式中所示(i) 通过含NCO的预聚物与氨基硅烷的反应或(ii) 通过OH封端的预聚物,例如聚醚、聚氨酯或聚酯与NCO官能的硅烷的反应制成的高分子量骨架:
但是,基于硅烷改性聚脲的涂料、胶粘剂和密封剂的缺点是它们的预聚物的高粘度。由于高粘度,只能在有限程度上使用硅烷改性聚脲,因为所用涂料或密封剂通常必须以液态至糊态施涂到要涂覆或胶粘的基底部件上。太粘的预聚物因此难以或不可能用作涂料、胶粘剂和/或密封剂。
此外,作为硅烷交联后的最终产物的所得涂层、胶粘点和/或封口的硬度对各自的用途至关重要。在硅烷改性聚脲的情况下,通常存在具有高硬度的最终产物。相反,硅烷改性聚氨酯在固化后提供较软的最终产物。但是,由于相对昂贵的NCO官能化硅烷前体,具有高硅烷含量的硅烷改性聚氨酯的合成难以经济地进行。
硅烷改性聚合物中的单体NCO含量另外在这方面起到重要作用:由于异氰酸酯的不可忽略的蒸气压(甚至在室温下),在喷雾施涂过程中就会形成可能对健康有害或至少致敏的异氰酸酯蒸气。因此,基本不含异氰酸酯单体并在任何情况下都低于0.018 mg/m3 NCO的根据危险物质的技术规定 (TRGS) 430(版本3/2009)的暴露限值(总反应性异氰酸酯基团浓度TRIG),优选低于0.01 mg/m3,特别优选低于0.001 mg/m3的反应性预聚物的研发是希望的。
发明目的
本发明的目的因此是提供由便宜易得的原材料制成的改进的反应性单组分胶粘剂和/或涂料体系,所述体系尽可能对健康无害并基本避免已知硅烷改性聚合物的上述问题。
特别提供由于较低粘度和较低结晶度而在操作上更简单并同时实现最终产物的高化学稳定性的反应性单组分胶粘剂体系。还力求的是可廉价制备并具有性质,特别例如固化度和化学稳定性的有利平衡的聚合最终产物。
发明概述
本发明涉及根据专利权利要求1的式(I)的化合物,其适合作为用于各种基底材料,例如金属、木材、玻璃和/或塑料的改进的涂覆、胶粘和/或密封的单组分胶粘剂体系/涂料体系。在最终固化状态下,本发明提供作为永久涂料、胶粘剂和/或密封剂的经–Si-O-Si-桥缩合的聚合物。
本发明还提供用于制备式(I)和式(IV)的化合物的方法。
发明详述
根据本发明,提供式(I)的化合物:
其中在式(I)中:
Y代表m价分子基团,其是单异氰酸酯(m = 1)、多异氰酸酯(m > 1)或含异氰酸酯基团的预聚物(m = 1至20)减去m个NCO基团的结构单元;
R1代表具有1至12个碳原子的至少二价的任选取代的直链或支化的脂族、脂环族、芳脂族和/或芳族结构单元,其中一个或多个不相邻亚甲基可各自被O或S替代;
R2和R3各自彼此独立地代表具有1至12个碳原子的任选取代的直链或支化的脂族基团;
n代表0至2的整数;且
m代表1至20的数值。
在根据本发明的一个实施方案中,因此提供式(I)的化合物。
在根据本发明的另一实施方案中,提供用于制备式(I)的化合物的方法,其包括使式(Ia)的硅烷改性甲酰胺与式Y-(NCO)m的异氰酸酯反应:
其中Y、R1、R2、R3、n和m如权利要求1中所定义。
在根据本发明的另一实施方案中,提供包含至少一种式(I)的化合物的反应性单组分胶粘剂体系和/或涂料体系。
根据本发明,式(I)的化合物用于制造胶粘剂和密封剂、漆料、涂料、浆料(Schlichten)、墨水和/或印刷油墨。
在根据本发明的另一实施方案中,描述了根据本发明的反应性单组分胶粘剂体系用于胶粘和/或密封金属、木材、木基材料(Holzwerkstoff)、玻璃、皮革、织物、塑料、矿物材料、软木、纤维、混凝土、纸、纸板和薄膜的用途。
根据本发明另外公开了通过本发明的单组分胶粘剂体系接合的复合体。
定义
本申请中所用的术语“脂环族”是指不属于芳族化合物的碳环或杂环化合物,例如环烷、环烯或氧杂-、硫杂-、氮杂-或硫氮杂(Thiaza)-环烷。其具体实例是环己基、环戊基及其被一个或两个N或O原子中断的衍生物,例如嘧啶、吡嗪、四氢吡喃或四氢呋喃。
本申请中所用的术语“芳脂族”是指被芳基取代的烷基,例如苄基、苯基乙基、联苯基等。
本申请中所用的术语“任选取代的”或“取代的”特别是指相关结构单元被-F、-Cl、-I、-Br、-OH、-OCH3、-OCH2CH3、-O-正丙基或–O-异丙基、-OCF3、-CF3、-S-C1-6-烷基和/或另一任选经杂原子键合的具有1至12个碳原子的直链或支化的脂族、脂环族、芳脂族和/或芳族结构单元取代。其优选是指被卤素(特别是-F、-Cl)、C1-6-烷氧基(特别是甲氧基和乙氧基)、羟基、三氟甲基和三氟甲氧基取代。
本申请中所用的术语“低分子量”是指分子质量不超过大约800 g·mol-1的化合物。
本申请中所用的术语“高分子量”是指分子质量超过大约800 g·mol-1的化合物。
在分子质量不遵循确切定义的结构式的化合物的情况下,例如在聚合物的情况下,分子质量在每种情况下被理解为是数均分子量。
本申请中所用的术语“单异氰酸酯”是指A-NCO所示的化合物,其中A代表具有6至50个碳原子的芳族、芳脂族、脂族或脂环族基团。
本申请中所用的术语“多异氰酸酯”是指具有优选≥ 2的NCO官能度的芳族、芳脂族、脂族或脂环族多异氰酸酯,特别是二-和三-异氰酸酯。
本申请中所用的术语“单体”是指参与低聚物和/或(预)聚合物的构成并具有特定摩尔质量的含官能团的低分子量化合物。
本申请中所用的术语“低聚物”是指其中只有少数具有相同或不同类型的单体重复相互键合的化合物。
本申请中所用的术语“预聚物”是指参与聚合物的最终构成的含官能团的低聚化合物。
本申请中所用的术语“聚合物”是指其中具有相同或不同类型的单体、低聚物和/或预聚物重复相互键合并且在聚合度、摩尔质量分布或链长方面可不同的高分子量化合物。
根据本发明的实施方案
下面详细描述根据本发明的实施方案。
式(I)的化合物
在一个实施方案中,提供通式(I)的化合物:
其中在式(I)中:
Y代表m价分子基团,其是单异氰酸酯(m = 1)、多异氰酸酯(m > 1)或含异氰酸酯基团的预聚物(m ≥ 1)减去m个NCO基团的结构单元;
R1代表具有1至12个碳原子的至少二价的任选取代的直链或支化的脂族、脂环族、芳脂族和/或芳族结构单元,其中一个或多个不相邻亚甲基可各自被O或S替代;
R2和R3各自彼此独立地代表具有1至12个碳原子的任选取代的直链或支化的脂族基团;
n代表0至2的整数;且
m代表1至20的数值,其中m也可以是分数。
在根据本发明的一个实施方案中,结构单元Y是衍生自单异氰酸酯的基团。此类单异氰酸酯的实例是异氰酸己酯、异氰酸6-氯己酯、异氰酸正辛酯、异氰酸环己酯、异氰酸2-乙基己酯、异氰酸2,3,4-甲基环己酯、异氰酸3,3,5-三甲基环己酯、异氰酸2-降冰片基-甲酯、异氰酸癸酯、异氰酸十二烷基酯、异氰酸十四烷基酯、异氰酸十六烷基酯、异氰酸十八烷基酯、异氰酸3-丁氧基丙酯、异氰酸3-(2-乙基己氧基)-丙酯、异氰酸苯酯、异氰酸甲苯酯、异氰酸氯苯酯(2,3,4-异构体)、异氰酸二氯苯酯、异氰酸4-硝基苯酯、异氰酸3-三氟甲基苯酯、异氰酸苄酯、异氰酸二甲基苯酯(工业混合物和独立异构体)、异氰酸4-十二烷基苯酯、异氰酸4-环己基-苯酯、异氰酸1-萘酯、来自1摩尔二异氰酸酯和1摩尔单羧酸,优选甲苯二异氰酸酯、二苯基甲烷二异氰酸酯和六亚甲基二异氰酸酯与具有优选至少6个碳原子的脂族单羧酸的异氰酸根合酰胺,例如(6-异氰酸根合己基)-硬脂酸酰胺、(3-异氰酸根合甲苯基)-硬脂酸酰胺、(6-异氰酸根合己基)-苯甲酰胺,它们在每种情况中独自或与多种单异氰酸酯混合。
在根据本发明的另一实施方案中,结构单元Y是衍生自多异氰酸酯的基团。使用本身为本领域技术人员已知的具有优选≥ 2的NCO官能度的芳族、芳脂族、脂族或脂环族多异氰酸酯作为合适的多异氰酸酯。这些也可具有亚氨代噁二嗪二酮、异氰脲酸酯、脲二酮、氨基甲酸酯、脲基甲酸酯、缩二脲、脲、噁二嗪三酮、噁唑烷酮、酰基脲和/或碳二亚胺结构。
上文提到的多异氰酸基于本身为本领域技术人员已知的具有脂族、脂环族、芳脂族和/或芳族键合的异氰酸酯基团的二-或三-异氰酸酯,其中它们是否使用光气或是通过无光气法制成是不重要的。此类二-和三-异氰酸酯的实例是1,4-二异氰酸根合丁烷、1,5-二异氰酸根合戊烷、1,6-二异氰酸根合己烷(HDI)、2-甲基-1,5-二异氰酸根合戊烷、1,5-二异氰酸根合-2,2-二甲基戊烷、2,2,4-和/或2,4,4-三甲基-1,6-二异氰酸根合己烷、1,10-二异氰酸根合癸烷、1,3-和1,4-二异氰酸根合环己烷、1,3-和1,4-双(异氰酸根合甲基)环己烷、1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷(异佛尔酮二异氰酸酯,IPDI)、4,4'-二异氰酸根合二环己基甲烷(Desmodur® W, Bayer AG, Leverkusen, DE)、4-异氰酸根合甲基-1,8-辛烷二异氰酸酯(三异氰酸根合壬烷,TIN)、二异氰酸根合-1,3-二甲基环己烷(H6XDI)、1-异氰酸根合-1-甲基-3-异氰酸根合甲基环己烷、1-异氰酸根合-1-甲基-4-异氰酸根合甲基环己烷、双(异氰酸根合甲基)降冰片烷、1,5-萘二异氰酸酯、1,3-和1,4-双(2-异氰酸根合丙-2-基)苯(TMXDI)、2,4-和2,6-二异氰酸根合甲苯(TDI),特别是2,4-和2,6-异构体和这两种异构体的工业混合物,2,4'-和4,4'-二异氰酸根合二苯基甲烷(MDI)、1,5-二异氰酸根合萘、1,3-双(异氰酸根合甲基)苯(XDI)和所述化合物的任意混合物。
该多异氰酸酯特别优选具有2.0至5.0,最特别优选2.3至4.5的平均NCO官能度和优选5.0至27.0重量%,特别优选14.0至24.0重量%的异氰酸酯基团含量,和优选小于1重量%,特别优选小于0.5重量%的单体二异氰酸酯含量。
优选使用仅具有脂族和/或脂环族键合的异氰酸酯基团的上述类型的多异氰酸酯或多异氰酸酯混合物。
上述类型的多异氰酸酯特别优选基于六亚甲基二异氰酸酯、异佛尔酮二异氰酸酯、异构的双-(4,4'-异氰酸根合环己基)-甲烷、TDI、MDI及其混合物。
在根据本发明的另一实施方案中,结构单元Y是衍生自带有异氰酸酯基团的预聚物的基团。这特别可以是聚氨酯预聚物。带有异氰酸酯基团的聚氨酯预聚物Y-(NCO)m的根据本发明的制备包括使一种或多种已提到的多异氰酸酯与一种或多种多元醇反应。
作为合适的多元醇,可以使用本身为本领域技术人员从聚氨酯化学中已知的所有多元醇,所述多元醇优选具有≥ 1.5,特别优选1.8至2.5的平均OH官能度。
它们可以是例如低分子量二醇(例如1,2-乙二醇、1,3-或1,2-丙二醇、1,4-丁二醇、2,2,4-三甲基戊二醇)、三醇(例如甘油、三羟甲基丙烷)和四醇(例如季戊四醇)、聚醚多元醇、聚酯多元醇、聚丙烯酸酯多元醇以及聚碳酸酯多元醇。优选的多元醇是基于聚醚的上述类型的物质。
当使用聚醚多元醇时,使用具有优选300至20000 g/mol,特别优选1000至12000g/mol,最特别优选2000至6000 g/mol的数均分子量Mn的聚醚多元醇。
此外,它们优选具有≥ 1.9,特别优选≥ 1.95的平均OH官能度。
这些聚醚的OH官能度优选< 6,特别优选< 4,最特别优选< 2.2。
同样合适的多元醇是来自合适的醇和酸的缩合反应的聚酯多元醇。使用伯和二伯二醇,如乙二醇、二乙二醇、三乙二醇、1,2-丙二醇、二丙二醇、1,3-丁二醇、1,4-丁二醇、1,6-己二醇或新戊二醇以及更多元醇,如三羟甲基丙烷、三羟甲基乙烷或季戊四醇作为醇。合适的缩合配对物是酸组分,如己二酸或邻苯二甲酸。使用金属催化剂,例如乙基己酸锡(II)或四烷氧基化钛和作为起始剂的上述类型的二醇或三醇的ε-己内酯或甲基-ε-己内酯的开环聚合也产生合适的聚酯多元醇。这些聚酯多元醇的长度在此取决于所用己内酯单元数。
聚酯多元醇的优选分子量(数均)为≤ 1000 g/mol。聚酯多元醇的优选官能度为2至3。
聚丙烯酸酯多元醇也适用于制备本发明的预聚物。该聚丙烯酸酯多元醇具有200至10000 g/mol,特别优选200至6000 g/mol,最特别优选200至2500 g/mol的数均分子量。所用聚丙烯酸酯多元醇的官能度优选为1.6至3.8,特别优选1.8至3.5。这些聚丙烯酸酯多元醇的OH值优选为15至150,特别优选20至100,最特别优选40至80 mg KOH/g。Acryflow®P60和P90(来自Lyondell, US的商品)例如合适。
脂族聚碳酸酯多元醇也考虑用于本发明的预聚物的构成。聚碳酸酯多元醇如已知的那样可由光气与多元醇的缩合反应或由合适的有机碳酸酯与多元醇的酯交换获得。作为有机碳酸酯,考虑碳酸芳基酯、碳酸烷基酯和碳酸亚烷基酯及其混合物。可提到的实例是碳酸二苯酯(DPC)、碳酸二甲酯(DMC)、碳酸二乙酯(DEC)和碳酸亚乙酯。作为多元醇,考虑上文在聚酯多元醇部分下提到的多元醇。所用聚碳酸酯多元醇的官能度优选为1.6至3.8,特别优选1.8至3.5。这些聚碳酸酯多元醇具有优选100至6000 g/mol,特别优选100至4000 g/mol的数均摩尔重量。OH值取决于聚碳酸酯多元醇的官能度并通常为20至900 mg KOH/g。
其它合适的多元醇也是例如EP-A 0 689 556和EP-A 0 937 110中描述的特定多元醇,其例如可通过环氧化脂肪酸酯与脂族或芳族多元醇在环氧化物开环下的反应获得。
含羟基的聚丁二烯同样可用作多元醇。
根据本发明的聚氨酯预聚物Y-(NCO)m的制备原则上以聚氨酯化学中已知的方式进行。在此使多元醇(独立或以混合物形式)与过量多异氰酸酯(独立或以混合物形式)任选在催化剂和/或助剂和添加剂存在下反应。搅拌该均匀反应混合物直至达到恒定NCO值。然后可通过连续蒸馏除去任选未反应的多异氰酸酯。
连续蒸馏法在本发明的含义内被理解为是只有各自部分量的来自上述方法步骤的预聚物短暂暴露在升高的温度下,而尚未经过蒸馏过程的量仍在明显较低的温度下的方法。升高的温度在此被理解为是挥发性成分在相应选择的压力下的蒸发温度。
该蒸馏优选在低于170℃,特别优选110至170℃,最特别优选125至145℃的温度和小于20毫巴,特别优选小于10毫巴,最特别优选0.05至5毫巴的压力下进行。
尚未经过蒸馏过程的量的含预聚物的反应混合物的温度优选为0至60℃,特别优选15至40℃,最特别优选20至40℃。
在本发明的一个优选实施方案中,蒸馏温度与尚未经过蒸馏过程的量的含预聚物的反应混合物的温度之间的温度差为至少5℃,特别优选至少15℃,最特别优选15至40℃。
优选以这样的速度进行蒸馏,以使待蒸馏的含预聚物的反应混合物的体积增量暴露在蒸馏温度下少于10分钟,特别优选少于5分钟,然后任选通过主动冷却重新达到含预聚物的反应混合物在蒸馏前的起始温度。在此经历的温度荷载优选使得蒸馏前的反应混合物的温度或蒸馏后的预聚物的温度比使用的蒸馏温度高至少5℃,特别优选至少15℃,最特别优选15至40℃。
优选的连续蒸馏技术是短程蒸馏、降膜蒸馏和/或薄膜蒸馏(对此参见例如Chemische Technik, Wiley-VCH, 第1卷, 第5版, 第333-334页)。
降膜蒸发器由固定长管束构成,从顶部向其中引入待蒸发的液体并以薄膜形式向下流动。在夹套腔中通过蒸汽进行加热。在管中形成蒸气泡,其随液体向下流动并确保湍流条件。在底端在分离器中分离蒸气和液体。
薄膜蒸发器是适用于蒸发只能短暂受热的对温度敏感物质的装置。待蒸发的液体从顶部引入具有夹套加热的管中。其以薄膜形式在该管中向下流动。在该管内,悬挂在轴上的刮片旋转并确保恒定薄膜厚度。优选使用具有上述参数的薄膜蒸馏作为连续蒸馏技术。
该反应中的多异氰酸酯的NCO基团与多元醇的OH基团的当量比优选为10:1至2:1,特别优选7:1至2:1。
所选反应温度为0℃至250℃,优选20℃至140℃,最特别优选40℃至100℃。
本发明的方法当然也可以在溶剂,如芳族化合物、氯代芳族化合物、酯或氯代烃存在下进行。
为了加速氨基甲酸酯化,可以使用本身已知的催化剂,如有机金属化合物、胺(例如叔胺)或金属化合物,如辛酸铅、琥珀酸汞、三氟甲磺酸锌、辛酸锡或二月桂酸二丁基锡。如果一起使用催化剂,它们优选以待反应的多异氰酸酯和多元醇的总量的0.001至5重量%,特别是0.002至2重量%的量添加。
式(I)和(III)中的优选取代基含义
优选提供式(I)和(III)的化合物,其中在每种情况下:
R代表亚甲基(-CH2-)、亚乙基(-CH2CH2-)、亚丙基(-CH2CH2CH2-)、亚异佛尔酮基(Isophorylene)、4,4'-二环己基亚甲基、双(亚环己基)、4,4'-亚联苯基、邻-、间-或对-亚甲苯基或亚己基(特别是-CH2CH2CH2CH2CH2CH2-),特别优选亚正己基;
R1代表亚甲基(-CH2-)或亚丙基(特别是亚正丙基-CH2CH2CH2-),特别优选亚正丙基;
R2和R3各自彼此独立地代表甲基或乙基,优选乙基;且
n代表0至2的整数。
特别优选提供式(I)和/或(III)的化合物,其中在每种情况下:
R代表亚异佛尔酮基、4,4'-二环己基亚甲基、双(亚环己基)、亚联苯基、亚甲苯基或亚正己基;
R1代表亚正丙基;
R2和R3各自彼此独立地代表甲基或乙基;且
n代表0至2的整数。
最特别优选提供式(III)的化合物,其中R是亚异佛尔酮基、亚甲苯基或亚正己基,R1是亚正丙基,R2和R3是甲基且n = 0。
根据本发明的式(I)的化合物适合作为涂料、胶粘剂和/或密封剂的胶粘剂。
根据本发明的式(I)的化合物具有100至1000000 mPa·s,优选1000至500000mPa·s,特别优选5000至300000 mPa·s的粘度(在23℃下)。
由于存在的酰基脲基团,根据本发明的式(I)的化合物与含脲基的类似产物相比具有较低粘度。如本领域技术人员已知,这带来改进的可操作性或产生着色涂料的进一步加工,或用于配制胶粘剂或密封剂的填料例如白垩的更好的掺入。
制备式(I)的化合物的方法
根据本发明的式(I)的化合物可通过下列两步法制备:
优选首先将过量甲酸烷基酯R'O-CHO逐滴添加到胺H2N-R1-Si(R2)n(OR3)3-n中,其中R'优选代表具有1至4个碳原子的烷基。甲酸甲酯或甲酸乙酯特别优选作为甲酸烷基酯R'O-CHO。优选使1摩尔胺与1.01至6摩尔,特别优选1.05至4摩尔的过量甲酸烷基酯R'O-CHO在该甲酸烷基酯的沸点温度下反应。在反应完成时,借助薄膜蒸馏蒸馏出过量甲酸烷基酯R'O-CHO和所得醇R'-OH并任选过滤出所得产物(Ia)。
然后使式(Ia)的化合物与Y-(NCO)m优选在惰性条件下在20至200℃,优选40至160℃的温度下反应。这两种组分在此以至少1:10至最高40:1,优选1:5至最高30:1,特别优选1:2至最高25:1的异氰酸酯基团:甲酰胺基团当量比使用。该反应可以在溶液中或无溶剂在本体(Substanz)中进行。
具有式(I)的化合物的制备可以不用催化剂进行。但是,也可任选加入已知催化剂以加速该反应。可以使用例如叔胺,例如三乙胺、三丁胺、二甲基苄胺、二乙基苄胺、吡啶、甲基吡啶、二环己基甲基胺、二甲基-环己基胺、N,N,N',N'-四甲基二氨基二乙醚、双-(二甲基氨基丙基)-脲、N-甲基-或N-乙基-吗啉、N-椰油吗啉、N-环己基吗啉、N,N,N',N'-四甲基乙二胺、N,N,N',N'-四甲基-1,3-丁二胺、N,N,N',N'-四甲基-1,6-己二胺、五甲基二乙三胺、N-甲基哌啶、N-二甲基-氨基乙基哌啶、N,N'-二甲基哌嗪、N-甲基-N'-二甲基氨基哌嗪、1,2-二甲基咪唑、2-甲基咪唑、N,N-二甲基咪唑-β-苯基乙基胺、1,4-二氮杂双环-(2,2,2)-辛烷(DABCO)和己二酸双-(N,N-二甲基氨基乙基)酯,脒,例如1,5-二氮杂双环[4.3.0]壬烯(DBN)、1,8-二氮杂双环(5.4.0)十一-7-烯(DBU)和2,3-二甲基-3,4,5,6-四氢嘧啶,烷醇胺化合物,例如三乙醇胺、三异丙醇胺、N-甲基二乙醇胺、N-乙基-二乙醇胺、二甲基氨基乙醇和2-(N,N-二甲基氨基乙氧基)乙醇,N,N',N"-三-(二烷基氨基烷基)六氢三嗪,例如N,N',N"-三-(二甲基氨基丙基)-均-六氢三嗪、双(二甲基氨基乙基)醚以及金属盐,例如铁、铅、铋、锌和/或锡在该金属的常规氧化态下的无机和/或有机化合物,例如氯化铁(II)、氯化铁(III)、2-乙基己酸铋(III)、辛酸铋(III)、新癸酸铋(III)、氯化锌、2-乙基己酸锌、三氟甲磺酸锌(II)、辛酸锡(II)、乙基己酸锡(II)、棕榈酸锡(II)、二月桂酸二丁基锡(IV)(DBTL)、二氯化二丁基锡(IV)或辛酸铅。
所用的优选催化剂是叔胺、脒和上述类型的锡化合物或锌化合物。特别优选的催化剂是1,4-二氮杂双环-(2,2,2)-辛烷(DABCO)、1,5-二氮杂双环[4.3.0]壬烯(DBN)、1,8-二氮杂双环(5.4.0)十一-7-烯(DBU)以及二月桂酸二丁基锡(IV)(DBTL)和三氟甲磺酸锌(II)。
上文举例提到的催化剂可独自或以任意混合物的形式用于该反应,并且如果使用,作为所用催化剂总量计算,以所用起始化合物的总量的0.001至1.0重量%,优选0.01至0.5重量%的量使用。
可以例如通过滴定法测定NCO含量来监测反应进程。在达到所需NCO含量后,终止该反应。
由此制备的式(I)的化合物是清澈的几乎无色产物,其根据所选原材料,是低至高粘度液体并具有反应产物总质量的少于1.0重量%,优选少于0.5重量%,特别优选少于0.3重量%的单体起始二异氰酸酯残留含量。
可通过添加甲醇捕获(abgefangen)可能仍可检出的残留NCO含量。
为了防止在本发明的方法的过程中式(I)的化合物的硅烷基团的过早交联,可以有利地加入去水剂(Wasserfänger)。例如,可以使用原甲酸酯,例如原甲酸三乙酯,乙烯基硅烷,例如乙烯基三甲氧基硅烷,或有机磷酸酯,例如磷酸二丁酯。如果必要,去水剂以原材料总量的最多5重量%,优选最多2重量%的量使用。
如果使用催化剂和/或去水剂,可以在实际反应开始前将它们添加到起始化合物中。但是也可以在反应过程中的任意时间点将这些助剂添加到反应混合物中。
在一个优选实施方案中,本文所述的方法在保护气体气氛,例如氮气下进行。
本文中公开的式(I)的硅烷改性聚合物可根据本发明用于制造胶粘剂和密封剂、漆料、涂料、浆料、墨水和/或印刷油墨。
这种方法的优点在于,通过所用的式Y-(NCO)m的结构,可以使式(I)的硅烷改性聚合物的性质适应大量极为不同的用途。
反应性单组分胶粘剂体系
根据本发明,式(I)的化合物用于反应性单组分胶粘剂体系。该反应性单组分胶粘剂体系的特征在于其包含至少一种式(I)的化合物。
在水分或水的作用下,发生硅烷基团的可水解基团的水解,由此形成的硅烷醇接着交联(固化)并裂解出水。
也可一起使用加速硅烷醇基团水解和缩合的催化剂。这样的催化剂是本领域技术人员已知的。可以使用例如酸,例如硫酸、对甲苯磺酸、三氟甲磺酸、乙酸、三氟乙酸和磷酸二丁酯,碱,例如N-取代的脒,如1,5-二氮杂双环[4.3.0]壬-5-烯(DBN)和1,5-二氮杂双环[5.4.0]十一-7-烯(DBU),以及金属盐和金属螯合物,例如钛酸四异丙酯、钛酸四丁酯、乙酰丙酮钛(IV)、三仲丁酸铝、乙酰丙酮铝、三氟甲磺酸铝或三氟甲磺酸锡。
如果使用,这些催化剂以所用硅烷改性预聚物重量的最多5重量%,优选最多2重量%的量使用。根据所用催化剂的性质和量,由根据本发明的式(I)的化合物配制的单组分胶粘剂体系的固化可以在宽温度范围,例如-20至200℃,优选0至180℃,特别优选20至160℃内进行。
任意其它可水解硅烷化合物,例如四甲氧基硅烷、四乙氧基硅烷、甲基三甲氧基硅烷、甲基三乙氧基硅烷、乙基三乙氧基硅烷、异丁基三甲氧基硅烷、异丁基三乙氧基硅烷、辛基三乙氧基硅烷、辛基三甲氧基硅烷、(3-环氧丙氧基丙基)-甲基二乙氧基硅烷、(3-环氧丙氧基丙基)三甲氧基硅烷、苯基三甲氧基硅烷、苯基三乙氧基硅烷或US 4 499 150中提到的类型的硅烷官能共聚物或此类硅烷化合物的混合物任选也可作为反应配对物添加到根据本发明的反应性单组分胶粘剂体系中。
本发明的反应性单组分胶粘剂体系同样可任选包含现有技术中已知的附加添加剂和/或助剂。可提到例如颜料、抗氧化剂、去水剂、填料、助滑添加剂、流动剂、流变添加剂、泡沫稳定剂、疏水剂、空隙形成剂、增粘添加剂(增粘剂)、配混剂、增塑剂、抗老化剂、阻燃剂和/或UV稳定剂。
作为合适的填料,可提到例如炭黑、沉淀二氧化硅、热解二氧化硅、矿物白垩和沉淀白垩。可提到的合适增塑剂的实例是邻苯二甲酸酯、己二酸酯、酚的烷基磺酸酯、磷酸酯或较高分子量聚丙二醇。
作为去水剂,特别可提到烷氧基甲硅烷基化合物,如乙烯基三甲氧基硅烷、甲基三甲氧基硅烷、异丁基三甲氧基硅烷、十六烷基三甲氧基硅烷。
作为增粘剂,使用已知的官能硅烷,例如上文提到的类型的氨基硅烷,以及N-氨基乙基-3-氨基-丙基-三甲氧基硅烷和/或N-氨基乙基-3-氨基丙基-甲基-二甲氧基硅烷、环氧硅烷和/或巯基硅烷。
除用作单组分胶粘剂体系外,根据本发明的式(I)的化合物也可例如作为添加剂混合到常规单组分和/或双组分聚氨酯胶粘剂体系中。
如果将如上所述的根据本发明的反应性单组分胶粘剂体系预先施涂到要胶粘的基底上,由于上述交联而发生基底的永久胶粘或密封。
要胶粘的基底的表面可能任选必须通过物理、化学和/或物理-化学法预处理。例如,底漆或增粘剂组合物的施涂在此有利,但根据本发明不一定必须。其因此在一个实施方案中也可省略。
基底
适合通过根据本发明的反应性单组分胶粘剂体系胶粘和/或密封的合适基底是金属、玻璃、木材、混凝土、石材、陶瓷、织物和/或塑料。要胶粘的基底可以相同或不同。
在一个优选实施方案中,根据本发明的反应性单组分胶粘剂体系用于金属、玻璃和/或塑料的胶粘和/或密封。
合适的金属基底通常可以由本领域中常规的所有金属或金属合金制成。优选使用金属,例如铝、不锈钢、钢、钛、含铁金属和合金。要胶粘的基底可另外由不同金属构成。
要胶粘的塑料基底是例如聚碳酸酯(PC)、聚酰胺、聚氯乙烯、聚氨酯、聚乙酸乙烯酯、聚丙烯酸酯或聚甲基丙烯酸酯、聚乙烯、聚苯乙烯、聚丙烯和/或聚酯,例如聚对苯二甲酸丁二醇酯(PBT)和/或聚对苯二甲酸乙二醇酯(PET)。
该基底可另外是经上漆或印刷的。
要胶粘的基底可进一步具有对于所得复合体的各自使用所需的各种任意形式。在最简单的形式中,该基底是平坦的。但也可以使用根据本发明的反应性单组分胶粘剂体系接合三维基底。
复合体
根据本发明还提供通过如上定义的根据本发明的反应性单组分胶粘剂体系接合的复合体。
实验部分
下列实施例用于说明本发明但绝对不应被解释为对保护范围的限制。
除非另行规定,所有百分比数据基于重量。
根据DIN EN ISO 11909滴定测定NCO含量。
根据DIN 53240-2: 2007-11滴定测定OH值并根据DIN 3682 5测定酸值。由分析测定的OH值计算所示OH含量。
根据DIN EN ISO 10283通过使用内标的气相色谱法测量残留单体含量。
通过根据DIN 55672-1(凝胶渗透色谱法(GPC) – 第1部分: 四氢呋喃(THF)作为洗脱剂)对照聚苯乙烯标样的凝胶渗透色谱法测定分子量,不同在于使用0.6毫升/分钟而非1.0毫升/分钟的流速进行操作。
使用来自Anton Paar Germany GmbH (DE)的Physica MCR 51流变仪根据DIN ENISO 3219进行所有粘度测量。
具有式(Ia)的硅烷改性甲酰胺的合成
:
实施例1: N-(3-三甲氧基甲硅烷基丙基)甲酰胺
将1075.8克(6摩尔)3-氨基丙基三甲氧基硅烷在室温下在氮气气氛下预先置于具有温度计、KPG搅拌器、回流冷凝器和滴液漏斗的烧瓶中。在搅拌下逐滴加入378.6克(6.3摩尔)甲酸甲酯,以使不超过50℃。在放热反应平息后,在室温下继续搅拌4小时,然后在减压下(0.1毫巴,在50℃下)蒸馏出过量甲酸甲酯和所得甲醇。获得具有在23℃下11 mPa·s的粘度的无色液体。
实施例2: N-(3-甲基二甲氧基甲硅烷基丙基)甲酰胺
将99.6克(0.6摩尔)3-氨基丙基甲基二甲氧基硅烷在室温下在氮气气氛下预先置于具有温度计、KPG搅拌器、回流冷凝器和滴液漏斗的烧瓶中。在搅拌下逐滴加入40.3克(0.67摩尔)甲酸甲酯,以使不超过50℃。在放热反应平息后,在室温下继续搅拌4小时,然后在减压下(0.1毫巴,在50℃下)蒸馏出过量甲酸甲酯和所得甲醇。获得无色液体。
实施例3: N-(3-三乙氧基甲硅烷基丙基)甲酰胺
将221.4克(1摩尔)3-氨基丙基-三乙氧基硅烷在室温下在氮气气氛下预先置于具有温度计、KPG搅拌器、回流冷凝器和滴液漏斗的烧瓶中。在搅拌下逐滴加入77.8克(1.05摩尔)甲酸乙酯,以使不超过50℃。在放热反应平息后,在室温下继续搅拌4小时,然后在减压下(0.1毫巴,在80℃下)蒸馏出过量甲酸乙酯和所得乙醇。获得具有在23℃下13 mPa·s的粘度的无色液体。
实施例4: N-(3-甲基二乙氧基甲硅烷基丙基)甲酰胺
将497.9克(2.6摩尔)3-氨基丙基甲基二乙氧基硅烷在室温下在氮气气氛下预先置于具有温度计、KPG搅拌器、回流冷凝器和滴液漏斗的烧瓶中。在搅拌下逐滴加入212.1克(2.8摩尔)甲酸乙酯,以使不超过50℃。在放热反应平息后,在室温下继续搅拌4小时,然后在减压下(0.1毫巴,在80℃下)蒸馏出过量甲酸乙酯和所得乙醇。获得具有在23℃下12mPa·s的粘度的无色液体。
具有通式(I)的硅烷改性化合物的合成
:
实施例5:
将154.5克(0.915摩尔)HDI和25毫克(30 ppm)三氟甲磺酸锌(II)在60℃下在氮气气氛下预先置于具有温度计、KPG搅拌器、回流冷凝器和滴液漏斗的烧瓶中。然后逐滴加入469.5克聚丙二醇(OH值: 112 mg KOH/g)和201克聚醚(OH值: 52 mg KOH/g)。在60℃下搅拌该反应混合物直至达到恒定异氰酸酯含量(3.0重量%)。然后计量加入142.8克(0.69摩尔)N-(3-三甲氧基甲硅烷基丙基)甲酰胺(来自实施例1)并在80℃下搅拌该反应混合物直至通过滴定法不再可检出异氰酸酯含量。为了稳定所得硅烷封端的预聚物,加入32毫克磷酸二丁酯并加入2.14克乙烯基三甲氧基硅烷作为去水剂。所得粘合剂是清澈无色物料并具有在23℃下21000 mPa·s的粘度。
实施例6:(实施例5的对比例)
将154.5克(0.915摩尔)HDI和25毫克(30 ppm)DBTL(二月桂酸二丁基锡)在60℃下在氮气气氛下预先置于具有温度计、KPG搅拌器、回流冷凝器和滴液漏斗的烧瓶中。然后逐滴加入469.5克聚丙二醇(OH值: 112 mg KOH/g)和201克聚醚(OH值: 52 mg KOH/g)。在60℃下搅拌该反应混合物直至达到恒定异氰酸酯含量(3.0重量%)。然后计量加入123.7克(0.69摩尔)3-氨基丙基三甲氧基硅烷并在80℃下搅拌该反应混合物直至通过滴定法不再可检出异氰酸酯含量。为了稳定所得硅烷封端的预聚物,加入32毫克磷酸二丁酯并加入2.14克乙烯基三甲氧基硅烷作为去水剂。所得粘合剂是浑浊白色物料并具有在23℃下100000 mPa·s的粘度。
实施例7:
将519.0克Desmodur® N 75 BA(来自Bayer MaterialScience AG的多异氰酸酯(基于HDI的缩二脲,75%在乙酸丁酯中);异氰酸酯含量16.5重量%)与50 ppm DABCO一起在80℃下在氮气气氛下预先置于具有温度计、KPG搅拌器、回流冷凝器和滴液漏斗的烧瓶中。在搅拌下逐滴加入518.0克(2.8摩尔)N-(3-三甲氧基甲硅烷基丙基)甲酰胺(来自实施例1)。在添加完成后,在80℃下搅拌该反应混合物直至通过滴定法不再可检出异氰酸酯含量。所得粘合剂具有在23℃下6240 mPa·s的粘度。
为了进一步加工,用乙酸丁酯将该粘合剂调节到50%固含量并加入0.25%来自BASF的Lupragen® N 700(1,8-二氮杂双环-5,4,0-十一-7-烯);以50微米的层厚度(湿)刮涂到玻璃板上。在23℃和50%相对空气湿度下4小时干燥时间后,该涂层触干并在4天后表现出对于二甲苯、乙酸1-甲氧基-2-丙酯、乙酸乙酯和丙酮的良好耐溶剂性。
实施例8:
将578.0克Desmodur® L75(来自Bayer MaterialScience AG的多异氰酸酯(基于TDI的多异氰酸酯,75%在乙酸乙酯中);异氰酸酯含量13.3重量%)与50 ppm DABCO一起在80℃下在氮气气氛下预先置于具有温度计、KPG搅拌器、回流冷凝器和滴液漏斗的烧瓶中。在搅拌下逐滴加入522.0克(2.5摩尔)N-(3-三甲氧基甲硅烷基丙基)甲酰胺(来自实施例1)。在添加完成后,在80℃下搅拌该反应混合物直至通过滴定法不再可检出异氰酸酯含量。所得粘合剂具有在23℃下92000 mPa·s的粘度。
为了进一步加工,用乙酸乙酯将该粘合剂调节到50%固含量并加入0.25%来自BASFSE的Lupragen® N 700(1,8-二氮杂双环-5,4,0-十一-7-烯);以50微米的层厚度(湿)刮涂到玻璃板上。在23℃和50%相对空气湿度下4小时干燥时间后,该涂层触干并在4天后表现出对于二甲苯、乙酸1-甲氧基-2-丙酯、乙酸乙酯和丙酮的良好耐溶剂性。
实施例9:
将201.6克(1.2摩尔)HDI在80℃下在氮气气氛下预先置于具有温度计、KPG搅拌器、回流冷凝器和滴液漏斗的烧瓶中,并逐份加入87.6克(0.6摩尔)2,2,4-三甲基戊-1,3-二醇。然后计量加入346克乙酸丁酯作为溶剂和52毫克三乙胺作为催化剂。在达到恒定异氰酸酯含量(8.2重量%)后,逐滴加入248.4克(1.2摩尔)N-(3-三甲氧基甲硅烷基丙基)甲酰胺(来自实施例1)并在80℃下搅拌该配制品直至通过滴定法不再可检出异氰酸酯含量。所得清澈粘合剂具有在50%固含量下41 mPa·s的粘度。
为了进一步加工,将0.25%来自BASF SE的Lupragen® N 700(1,8-二氮杂双环-5,4,0-十一-7-烯)添加到该粘合剂中,并以50微米的层厚度(湿)刮涂到玻璃板上。在23℃和50%相对空气湿度下4小时干燥时间后,该涂层触干并在4天后表现出对于二甲苯、乙酸1-甲氧基-2-丙酯、乙酸乙酯和丙酮的良好耐溶剂性。
实施例10:(实施例9的对比例)
将201.6克(1.2摩尔)HDI在80℃下在氮气气氛下预先置于具有温度计、KPG搅拌器、回流冷凝器和滴液漏斗的烧瓶中,并逐份加入87.6克(0.6摩尔)2,2,4-三甲基戊-1,3-二醇。然后计量加入346克乙酸丁酯作为溶剂和52毫克三乙胺作为催化剂。在达到恒定异氰酸酯含量(8.2重量%)后,逐滴加入215.1克(1.2摩尔)3-氨基丙基三甲氧基硅烷。在该添加开始后不久,该反应混合物变浑浊,且尽管进一步稀释到小于50%的固含量,该配制品在室温下凝固。该配制品不可能作为漆料粘合剂进一步加工。
胶粘剂和密封剂的应用技术例
为了评估来自实施例9的预聚物的应用技术性质,以下列配方加工它们:
以重量%计的用量 | |
聚合物 | 31.34 |
填料(Socal U<sub>1</sub>S<sub>2</sub>) | 47.01 |
增塑剂(Jayflex DINP) | 18.80 |
干燥剂(Dynasylan VTMO) | 1.88 |
增粘剂(Dynasylan 1146) | 0.94 |
催化剂(Lupragen N 700) | 0.03 |
为了制备制剂,将填料(来自Solvay的Socal® U1S2)、增塑剂(来自Exxon的JayflexTM DINP)和干燥剂(来自Evonik的Dynasylan® VTMO)添加到粘合剂中,并在具有壁刮刀的真空溶解器中在3000转/分钟下进行混合。然后加入增粘剂(来自Evonik的Dynasylan® 1146)并在1000转/分钟下在5分钟内拌入。最后,在1000转/分钟下搅入催化剂(来自BASF SE的Lupragen® N700)并最后使最终混合物在真空中脱气。
为了测量物理性质,根据DIN EN ISO 11600制备具有2毫米厚度的膜和在玻璃基底上的试样。根据DIN 53505在膜上进行肖氏硬度的测试。根据DIN EN ISO 11600在23℃下测量在50%伸长下的模量。
获得下列结果:
实施例15(来自实施例9的预聚物) | |
肖氏A硬度 | 52 |
50%模量[N/mm<sup>2</sup>] | 2.4 |
薄膜干燥时间,100µm [min] | 150 |
断裂伸长率[%] | 64.6 |
Claims (13)
1.通式(I)的化合物:
其中在式(I)中:
Y代表m价分子基团,其是单异氰酸酯,即m = 1,多异氰酸酯,即m > 1或含异氰酸酯基团的预聚物,即m = 1至20,减去m个NCO基团的结构单元;
R1代表具有1至12个碳原子的二价的任选取代的直链或支化的脂族、脂环族、芳脂族和/或芳族结构单元,其中一个或多个不相邻亚甲基可各自被O或S替代;
R2和R3各自彼此独立地代表具有1至12个碳原子的任选取代的直链或支化的脂族基团;
n代表0至2的整数;且
m代表1至20的数值。
2.根据权利要求1的化合物,其中R2和R3各自彼此独立地代表甲基或乙基。
3.根据权利要求1或2的化合物,其中Y代表分子基团,其是单异氰酸酯,即m = 1,多异氰酸酯,即m > 1或含异氰酸酯基团的预聚物,即m = 1至20,减去m个NCO基团的结构单元,R1代表亚丙基,R2和R3各自彼此独立地代表甲基或乙基,且n代表0至2的整数。
4.用于制备式(I)的化合物的方法,其包括使式(Ia)的化合物与式Y-(NCO)m的结构单元反应:
其中Y、R1、R2、R3、n和m如权利要求1中所定义。
5.根据权利要求1至3任一项的化合物用于制造胶粘剂和密封剂、漆料、涂料、浆料、墨水和/或印刷油墨的用途。
6.包含至少一种根据权利要求1至3任一项的化合物的反应性单组分胶粘剂体系。
7.根据权利要求6的反应性单组分胶粘剂体系用于胶粘和/或密封金属、木材、玻璃、皮革、织物、塑料、矿物材料、纤维、混凝土、纸和薄膜的用途。
8.包含根据权利要求6的反应性单组分胶粘剂体系的试剂盒,其用于胶粘和/或密封金属、木材、玻璃、皮革、织物、塑料、矿物材料、纤维、混凝土、纸和薄膜。
9.通过根据权利要求6的反应性单组分胶粘剂体系或通过根据权利要求8的试剂盒接合的复合体。
10.包含至少一种根据权利要求1至3任一项的化合物的反应性单组分涂料体系。
11.根据权利要求10的反应性单组分涂料体系用于涂覆金属、木材、玻璃、皮革、织物、塑料、矿物材料、纤维、混凝土、纸和薄膜的用途。
12.包含根据权利要求10的反应性单组分涂料体系的试剂盒,其用于涂覆金属、木材、玻璃、皮革、织物、塑料、矿物材料、纤维、混凝土、纸和薄膜。
13.通过根据权利要求10的反应性单组分涂料体系或通过根据权利要求12的试剂盒接合的复合体。
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EP3298058B1 (de) | 2015-05-21 | 2019-04-17 | Covestro Deutschland AG | Polyurethan-beschichtungszusammensetzungen |
WO2020089019A1 (de) | 2018-10-30 | 2020-05-07 | Covestro Deutschland Ag | Verfahren zur herstellung eines mehrschicht-lackaufbaus mit einer deckschicht aus silangruppen-enthaltenden prepolymeren |
US20210346912A1 (en) | 2018-10-30 | 2021-11-11 | Covestro Intellectual Property Gmbh & Co. Kg | Multi-layer paint structure with improved layer adhesion |
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