CN104066759B - 聚醚酯多元醇及其制备方法 - Google Patents
聚醚酯多元醇及其制备方法 Download PDFInfo
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- CN104066759B CN104066759B CN201380006358.9A CN201380006358A CN104066759B CN 104066759 B CN104066759 B CN 104066759B CN 201380006358 A CN201380006358 A CN 201380006358A CN 104066759 B CN104066759 B CN 104066759B
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- Prior art keywords
- mixture
- compound
- fatty acid
- anhydride
- polyester ether
- Prior art date
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 85
- 229920000728 polyester Polymers 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 59
- 229930195729 fatty acid Natural products 0.000 claims description 59
- 239000000194 fatty acid Substances 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 57
- -1 cyclic acid anhydride Chemical class 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000004814 polyurethane Substances 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 150000002148 esters Chemical class 0.000 claims description 25
- 229920002635 polyurethane Polymers 0.000 claims description 25
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 239000006260 foam Substances 0.000 claims description 23
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 22
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 16
- 150000002460 imidazoles Chemical group 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 14
- 239000003549 soybean oil Substances 0.000 claims description 13
- 235000012424 soybean oil Nutrition 0.000 claims description 13
- 229920000570 polyether Polymers 0.000 claims description 12
- 229940014800 succinic anhydride Drugs 0.000 claims description 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000001294 propane Substances 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 9
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- 150000008064 anhydrides Chemical class 0.000 claims description 8
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 7
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 6
- 150000001991 dicarboxylic acids Chemical group 0.000 claims description 6
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- 230000008569 process Effects 0.000 claims description 6
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
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- VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Natural products CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
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- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000011495 polyisocyanurate Substances 0.000 claims description 3
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 claims description 2
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims description 2
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- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 2
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- 150000005690 diesters Chemical class 0.000 claims description 2
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 229940038384 octadecane Drugs 0.000 claims description 2
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- 239000005056 polyisocyanate Substances 0.000 claims description 2
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- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims 1
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- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims 1
- 150000002596 lactones Chemical class 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 description 30
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 20
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- 229910052757 nitrogen Inorganic materials 0.000 description 16
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 13
- 230000002209 hydrophobic effect Effects 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229920005862 polyol Polymers 0.000 description 8
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
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- 229940113165 trimethylolpropane Drugs 0.000 description 7
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 6
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
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- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
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Abstract
本发明涉及新的聚醚酯多元醇及其制备方法。
Description
本发明涉及新的聚醚酯多元醇及其制备方法。
聚醚酯多元醇为在一条分子链中同时包括聚醚单元和聚酯单元的多元醇。它们特别用做制备聚氨酯材料的原料。用于获得聚醚酯多元醇的各种方法原则上是已知的。一些相关的文献现引用如下:
US 6 753 402记载了通过使用DMC催化剂将环氧烷催化加成至聚酯上。
US 5 319 006、US 5 436 313和US 5 696 225记载了通过使用缩聚催化剂使聚醚与二羧酸或酸酐进行缩聚反应。
US 6 569 352记载了一种两步法,其中第一步包括使多元醇与环状酸酐进行反应,第二步包括将环氧烷加成至在第一步中获得的中间体上。
US 20070265367、US 5 032 671和Journal of Applied PolymerScience,2007卷,第103期,第417-424页记载了环状酸酐和环状酯分别与作为引发剂的环氧烷和醇的直接共聚。
US 20060211830记载了一种两步法,其中第一步包含使含羟基的羧酸酯与环氧烷反应。反应产物随后在酯交换催化剂的存在下缩聚。
EP 1 923 417 B1记载了借助碱性催化剂在脂肪酸酯存在下H-官能化合物与环氧烷的反应。所述方法涉及同时进行烷氧基化反应和酯交换反应,因此据称获得了均质的聚醚酯。
即使在上述文献中记载了使用脂肪酸酯或羧酸或羧酸酯或羧酸酐作为原料制备聚醚酯多元醇,这些文献均未表明环氧烷的碱催化开环聚合除脂肪酸酯之外还可包括其他的酯或酸酐官能的分子。然而,这提供了一种获得新聚醚酯结构的途径,该聚醚酯结构还可通过选择功能性分子来进一步改性和优化至特定的应用,例如在聚氨酯中。
在许多应用中,例如与聚氨酯——由多元醇例如聚酯多元醇获得的聚氨酯——有关的应用中,疏水特性是所期望的。它们通常导致吸水性下降和抗水解性改善,即改善了聚氨酯部分的老化特性。此外,疏水改性的聚氨酯可具有改变的表面构造,其可反映在例如改善的耐滑性或更愉悦的触感(改善的触觉)上。下降的吸水性在涂料、粘合剂、密封剂、弹性体(CASE)应用中提供了明显的优势。这些应用通常指定在某些测试条件下的聚氨酯的最大吸水性,因为众所周知的是,在这些应用中具有相对较低吸水性的聚氨酯通常具有改善的性能。在烃发泡硬质聚氨酯泡沫配方中,疏水性多元醇是所期望的,因为疏水性多元醇改善了多元醇组分、发泡剂和异氰酸酯组分之间的相容性,即使相对较高比例的脂族或环脂族发泡剂(正戊烷或环戊烷)也会产生均质的多元醇组分。
然而,例如在以上引用文献中所体现的,在制备聚醚酯多元醇领域中的现有文献没有提供令人满意的方案来解决如何制备用于广泛应用的具有疏水特性的聚醚酯多元醇的问题。此外,制备聚醚酯多元醇的现有方法通常具有高的能量需求且通常非常昂贵和不方便,例如必须除去在反应过程中形成的水。
本发明的一个目的是提供一种简单且非常高效节能的制备用于广泛应用的具有疏水特性的聚醚酯多元醇的方法。该方法应当理想地提供均一和均质的的聚醚酯多元醇,该聚醚酯多元醇应当适用于聚氨酯(PU)应用。该方法应当能够使用廉价原料。
我们已经发现,该目的通过以下制备聚醚酯多元醇的方法而实现,所述方法借助亲核和/或碱性催化剂使混合物(A)与至少一种环氧烷v)反应,所述混合物(A)包含至少一种泽瓦夫活性(Zerevitinov-active)化合物i),至少一种选自二羧酸的环状酸酐的化合物ii),至少一种脂肪酸iiia)和/或其酯iiib)以及任选地至少一种选自环状单酯和二酯的化合物iv),其中至少一种泽瓦夫活性化合物i)选自具有1至8的官能度的羟基和/或氨基官能的化合物,并且其中所述脂肪酸酯iiib)选自不含羟基的脂肪酸酯,及其混合物。
本发明还提供了一种通过本发明的方法获得的聚醚酯多元醇,以及由本发明的方法获得的聚醚酯多元醇通过与二异氰酸酯或多异氰酸酯反应而制备发泡聚氨酯和/或致密聚氨酯的用途,以及通过本发明的方法获得的聚醚酯多元醇用于制备聚异氰脲酸酯泡沫的用途,以及由本发明的方法获得的聚醚酯多元醇用于制备涂料或粘合剂领域的致密聚氨酯的用途。
在本发明的一个优选的实施方案中,在至少一种环氧烷iv)加入之前,所述混合物(A)与亲核和/或碱性催化剂一起初始进料至反应容器中。
在本发明的一个优选的实施方案中,所述泽瓦夫活性化合物i)选自具有1至8的官能度的羟基和/或氨基官能的化合物。
在另一个优选的实施方案中,泽瓦夫活性化合物i)选自通常使用的具有2至8的官能度的多元醇或一元胺和多元胺,或者其与环氧烷(例如环氧丙烷或环氧乙烷以及其混合物)的反应产物。本文可提及的实例为水、丙二醇、乙二醇、二乙二醇、二丙二醇、新戊二醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、己二醇、戊二醇、3-甲基-1,5-戊二醇、1,12-十二烷二醇、甘油、三羟甲基丙烷、三乙醇胺、季戊四醇、山梨糖醇、蔗糖、氢醌、邻苯二酚、间苯二酚、双酚A、双酚F、1,3,5-三羟基苯、甲醛与带有羟甲基的苯酚或三聚氰胺或脲的缩合产物、脲、缩二脲、曼尼希碱、淀粉或淀粉衍生物、氨、乙醇胺、二乙醇胺、三乙醇胺、异丙醇胺、二异丙醇胺、三异丙醇胺、乙二胺、六亚甲基二胺、苯胺、二氨基苯的所有异构体、二氨基甲苯以及二氨基二苯基甲烷。
泽瓦夫活性化合物优选选自甘油、丙二醇、二丙二醇、乙二醇、二乙二醇、新戊二醇、三羟甲基丙烷、蔗糖、山梨糖醇、季戊四醇和双酚A及其混合物。
在本发明方法的一个实施方案中,二羧酸的环状酸酐ii)选自a)烯基琥珀酸酐、b)邻苯二甲酸酐、c)马来酸酐、d)琥珀酸酐和e)四氢邻苯二甲酸酐,及其混合物。
烯基琥珀酸酐a)优选选自C12-C20-烷基链取代的琥珀酸酐和分子量在500至2000g/mol之间的聚(异丁烯)琥珀酸酐。在本发明方法的一个实施方案中,至少一种烯基琥珀酸酐a)优选选自C18-和/或C16-烯基琥珀酸酐、聚(异丁烯)琥珀酸酐及其混合物。
在一个实施方案中,二羧酸的环状酸酐ii)也可以是衣康酸。
在本发明方法的一个实施方案中,至少一种环氧烷V)选自环氧丙烷、环氧乙烷、1,2-环氧丁烷、2,3-环氧丁烷、1,2-环氧戊烷、1-环氧辛烷、1-环氧癸烷、1-环氧十二烷、1-环氧十四烷、1-环氧十六烷、1-环氧十八烷、氧化苯乙烯、氧化环己烯、环氧丙基新十二烷酸酯、缩水甘油、表氯醇及其混合物。
环氧烷v)优选选自1,2-环氧丁烷、环氧丙烷、环氧乙烷。
在本发明方法的一个实施方案中,所述脂肪酸iiia)选自含羟基的脂肪酸、羟基改性的脂肪酸和不含羟基的脂肪酸,及其混合物。
在本发明方法的另一个实施方案中,所述脂肪酸iiia)选自饱和脂肪酸和不饱和的脂肪酸,以及其混合物。
在又一个实施方案中,脂肪酸iiia)选自饱和、单不饱和、二不饱和和三不饱和的脂肪酸、不含羟基的脂肪酸、含羟基的脂肪酸以及羟基改性的脂肪酸。脂肪酸iiia)优选选自丁酸、己酸、辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、油酸、蓖麻油酸、亚油酸、亚麻酸、花生四烯酸、二十碳五烯酸、二十二碳六烯酸、羟基改性的油酸、羟基改性的亚油酸、羟基改性的亚麻酸和羟基改性的蓖麻油酸。
本发明组分iiib)含义中的术语“脂肪酸酯”涉及脂肪酸的单酯、脂肪酸的二酯、脂肪酸的三酯或脂肪酸的聚酯;上述脂肪酸的三酯还称作甘油三酯。甘油三酯是植物和动物来源的天然脂肪或油的主要成分。为本发明目的的脂肪酸的聚酯为用脂肪酸聚酯化的多元醇。
因此,脂肪酸酯iiib)选自脂肪酸甘油三酯、羟基官能化的脂肪酸烷基酯和未羟基官能化的脂肪酸烷基酯。
在一个实施方案中,脂肪酸酯iiib)选自含羟基的脂肪酸酯、羟基改性的脂肪酸酯和不含羟基的脂肪酸酯,及其混合物。
适用的含羟基的脂肪酸酯包括,例如,蓖麻油酸酯或者多官能醇的脂肪酸单酯或聚酯,例如低聚糖的脂肪酸单酯或聚酯或多糖的脂肪酸单酯或聚酯。
在本发明的一个实施方案中,脂肪酸酯iiib)选自可可脂、椰子脂、棉花籽油、花生油、榛子油、核桃油、亚麻籽油、红花油、海洋动物脂肪(鲸骨脂)、猪脂、牛脂、鹅脂、乳脂、蓖麻油、大豆油、菜籽油、橄榄油、葵花籽油、棕榈油、葡萄籽油、黑孜然油、南瓜籽油、玉米胚芽油、小麦胚芽油、扁桃仁油、开心果油、杏仁油、澳洲坚果油、鳄梨油、沙棘油、芝麻油、大麻油、报春花油、野玫瑰油、羟基改性的大豆油、羟基改性的菜籽油、羟基改性的橄榄油、羟基改性的葵花籽油以及衍生的蓖麻油。
在一个优选实施方案中,脂肪酸酯iiib)选自鲸骨脂、牛脂、蓖麻油、大豆油、菜籽油、橄榄油、葵花籽油、羟基改性的大豆油、羟基改性的菜籽油、羟基改性的橄榄油、羟基改性的葵花籽油以及衍生的蓖麻油、棕榈油、羟基改性的棕榈油,及其混合物。
在一个实施方案中,脂肪酸酯iiib)优选选自蓖麻油、大豆油、棕榈油、菜籽油、葵花籽油、羟基改性的油、不饱和和/或饱和的C4-C22脂肪酸烷基酯,例如硬脂酸烷基酯、油酸烷基酯、亚油酸烷基酯、亚麻酸烷基酯、亚麻酸烷基酯、蓖麻油酸烷基酯或其混合物。脂肪酸酯iiib)极特别优选选自蓖麻油、大豆油、菜籽油、葵花籽油、棕榈油、羟基改性的大豆油、羟基改性的葵花籽油、羟基改性的棕榈油、羟基改性的菜籽油、及这些优选脂肪酸酯的甲酯和/或乙酯。
将羟基引入到羟基改性的油或羟基改性的脂肪酸可通过通常已知的方法进行,所述方法例如加氢甲酰化/氢化或环氧化/开环或臭氧分解、直接氧化、一氧化二氮氧化/还原。
在本发明方法的一个实施方案中,不存在化合物iv)。
在本发明方法的另一个实施方案中,存在至少一种化合物iv)。
化合物iv)优选选自γ-丁内酯、δ-戊内酯、ε-己内酯、(R,R)-丙交酯、(S,S)-丙交酯、内消旋丙交酯及其混合物;特别优选化合物iv)为ε-己内酯。
碱性和/或亲核催化剂可选自碱金属或碱土金属氢氧化物、碱金属或碱土金属醇盐、叔胺、N-杂环卡宾。
碱性和/或亲核催化剂优选选自叔胺。
碱性和/或亲核催化剂特别优选选自咪唑和咪唑衍生物,极特别优选咪唑。
在另一个优选的实施方案中,碱性和/或亲核催化剂选自N-杂环卡宾,且更优选选自基于N-烷基-和N-芳基取代的亚咪唑基(imidazolylidene)的N-杂环卡宾。
在一个优选的实施方案中,碱性和/或亲核催化剂选自三甲基胺、三乙基胺、三丙基胺、三丁基胺、N,N’-二甲基乙醇胺、N,N’-二甲基环己胺、二甲基乙基胺、二甲基丁基胺、N,N’-二甲基苯胺、4-二甲基氨基吡啶、N,N’-二甲基苄基胺、吡啶、咪唑、N-甲基咪唑、2-甲基咪唑、4-甲基咪唑、5-甲基咪唑、2-乙基-4-甲基咪唑、2,4-二甲基咪唑、1-羟丙基咪唑、2,4,5-三甲基咪唑、2-乙基咪唑、2-乙基-4-甲基咪唑、N-苯基咪唑、2-苯基咪唑、4-苯基咪唑、胍、烷基化胍、1,1,3,3-四甲基胍、7-甲基-1,5,7-三氮杂双环[4.4.0]癸-5-烯、1,5-二氮杂双环[4.3.0]-壬-5-烯、1,5-二氮杂双环[5.4.0]十一碳-7-烯,优选咪唑和二甲基乙醇胺(DMEOA)。
所提及的催化剂可单独使用或以彼此相关的任何所需的混合物使用。
制备聚醚酯多元醇的方法优选通过以下方式进行:首先将泽瓦夫活性化合物与二羧酸酐ii)以及脂肪酸iiia)和/或脂肪酸酯iiib)和碱性催化剂一起加入反应器中,然后将环氧烷连续计量加入反应器。在本发明的又一实施方案中,同样地,将泽瓦夫活性化合物i)和/或二羧酸酐ii)和/或脂肪酸酯iiib)和/或脂肪酸iiia)与环氧烷一起连续计量加入反应器。在又一个实施方案中,将所有组分同时加入或在合成过程中通过计量连续加入且连续移出反应产物,以使整个过程可以完全连续的方式进行。
与环氧烷的反应通常在80至200℃,优选100至160℃且更优选110至140℃的温度下进行。
当叔胺和/或N-杂环卡宾用作与环氧烷反应的催化剂时,催化剂浓度在50-5000ppm之间,且优选在100-1000ppm之间,基于最终产品的质量计,并且在反应之后不需要从反应产物中除去催化剂。
在一个优选的实施方案中,泽瓦夫活性化合物i)选自三羟甲基丙烷、甘油、新戊二醇、双酚A;羧酸的环状酸酐ii)选自C18-和/或C16-烯基琥珀酸酐;脂肪酸酯iiib)选自蓖麻油、大豆油、棕榈油;环氧烷v)为环氧丙烷;碱性和/或亲核催化剂选自二甲基乙醇胺(DMEOA)和咪唑。
在又一个优选的实施方案中,泽瓦夫活性化合物i)选自乙二醇、二乙二醇、丙二醇、二丙二醇、甘油和三羟甲基丙烷;羧酸的环状酸酐ii)选自邻苯二甲酸酐;脂肪酸iiia)选自油酸、硬脂酸、亚油酸、亚麻酸或其混合物;并且脂肪酸酯iiib)选自蓖麻油、大豆油、棕榈油和牛脂;环氧烷v)为环氧丙烷、环氧乙烷或其混合物;碱性和/或亲核催化剂选自二甲基乙醇胺(DMEOA)和咪唑。
本发明的聚醚酯多元醇通过环氧烷的开环聚合制备。它们是遥爪聚合物(telechels)且具有定义明确的分子量和官能度。官能度通常在1-8,优选2-6且更优选2-4的范围内,且OH值在20-1000mgKOH/g,优选20-800mgKOH/g,更优选100-600mgKOH/g之间。
本发明的聚醚酯多元醇优选包含5质量%至90质量%,优选5质量%至80质量%的衍生自脂肪酸iiia)和/或脂肪酸酯iiib)的单元,取决于预期的用途。
本发明的聚醚酯多元醇优选包含5质量%至80质量%的衍生自化合物ii)的单元,取决于预期的目的。
使用的碱性和/或亲核催化剂不仅可催化开环聚合反应还可另外地催化酸酐官能分子的酯交换反应,可产生均一的反应产物。产物性能不再受工艺参数的极大影响且产物具有较好的再现性。
本发明方法的一个优点是,均质的反应产物甚至可由极性差异非常大并因此纯形式互不相容的化合物而获得。与环氧烷的反应使得互不相容的分子相容并产生不仅包含聚醚单元还包含聚酯单元的均质反应产物。在碱催化的烷氧基化的情况下,一个原因是,如前所述,认为酯交换发生在该过程中与开环聚合同时发生并且确保了含酯分子链和含醚分子链的均匀分布。
本发明的方法还提供以下优势:与类似的常规方法相比其可在更低的温度下进行(因此是节能的),并且其不仅具有更好的时效性还提供更高的收率。
本发明的聚醚酯多元醇用于聚氨酯(PU)部件的用途是非常多样的。例如,它们可被用于发泡PU材料或致密PU材料,例如包装泡沫、柔性泡沫、硬质泡沫、半硬质泡沫、泡沫垫层(carpet foams)、自结皮泡沫(integral foams)、鞋底、汽车的保险杠和其他汽车外部部件、人造革、涂料、粘合剂、密封剂或弹性体。
本发明的多元醇可以这样一种羟值范围而获得:所述羟值范围内的这些多元醇,当用作聚氨酯体系中的主要多元醇时,更适合用于相对硬质的聚氨酯,例如硬质泡沫,涂料,粘合剂和密封剂。
如上所述,硬质泡沫可为聚氨酯或聚氰脲酸酯泡沫。当烷烃(例如戊烷)用作发泡剂时,本发明的多元醇具有另外的优点:通过使用甘油三酯和含有疏水侧链的酸酐而纳入疏水油基侧链增加了体系的戊烷相容性。同样可通过使用例如邻苯二甲酸酐而纳入芳族结构来增加泡沫的耐火性。
在合成中通过使用甘油三酯和酸酐而引入至多元醇的酯基团还提供另外提高的耐火性。这使得本发明的多元醇特别适用于硬质泡沫领域的应用。
在涂料、粘合剂和密封剂领域中,纳入疏水油基侧链和含有疏水侧链的酸酐导致增强的疏水性。增强的疏水性具有在聚氨酯制备和其性能方面的优势。长(开放)的适用期在制备用于上述应用的聚氨酯时是所期望的。在反应过程中,聚氨酯混合物部分的增强的疏水性降低了吸水性,延长了体系的适用期并降低了气泡的形成。增强的疏水性导致在完全反应的聚氨酯的最终性能中疏水性的增强。对水的吸收可降低聚氨酯的硬度和聚氨酯对基材的粘合性。在电子元件的护罩方面具有相对较低的吸水性的聚氨酯同样是所期望的,因为对水的吸收导致介电常数的增加和体积电阻率的降低。此外,疏水性聚氨酯更不易水解因此可更长地保持聚氨酯的性能不变。
本发明的多元醇可通过与二异氰酸酯反应而用于制备预聚物。因此,本发明的多元醇可用于制备聚氨酯材料,其不论是直接以结合的多元醇组分的形式还是以预聚物的形式。在这种情况下,预聚物-多元醇混合物中的预聚物部分可在10%至90%之间。例如当本发明的多元醇用于单一组分湿固化体系(例如涂料、粘合剂和密封材料)时,使用这些预聚物-多元醇混合物。
取决于所使用的原料,可制备应用范围广泛的产品。用于聚氨酯涂料或用于硬质聚氨酯泡沫的多元醇例如优选利用烯基琥珀酸酐作为组分ii)以及脂肪酸甘油三酯(例如蓖麻油)作为组分iiib)。
在硬质聚氰脲酸酯-聚氨酯泡沫的情况下,组分ii)优选邻苯二甲酸酐且组分iiib)优选大豆油或油酸甲酯。
由本发明方法获得的聚醚酯多元醇包含疏水组分,该疏水组分可通过脂肪酸酯iiib)或酸酐组分ii)纳入到产物中,因此在聚氨酯中可提供疏水多元醇的上述优势。如已通过举例方式提及的,特性可针对各种应用通过选择组分i)、ii)、iii)、iv)和v)的类型和量来调节。
实施例
以下实施例说明了本发明的某些方面;它们绝不意欲限制本发明的范围。
聚醚酯多元醇实施例A
将405.5g三羟甲基丙烷、3379.4g蓖麻油、495.4g邻苯二甲酸酐和1.5g咪唑初始进料至压力反应釜并在搅拌的同时用氮气惰化三次。然后将反应混合物加热至120℃并且与于120分钟内加入的722.5g环氧丙烷混合。一旦单体加入完成且达到恒定反应压力,用氮气汽提约30分钟真空蒸馏出易挥发物质,然后排放出产物,获得4855g粘的单相聚醚酯多元醇。产物具有以下的分析参数:
聚醚酯多元醇实施例B
将449.9g三羟甲基丙烷、3752.5g蓖麻油、509.9g Pentasize68(购自Trigon GmbH的C16/C18-烯基琥珀酸酐)和1.5g咪唑初始进料至压力反应釜并在搅拌的同时用氮气惰化三次。然后将反应混合物加热至120℃并与于60分钟内加入的290g环氧丙烷混合。一旦单体加入完成且达到恒定反应压力,用氮气汽提约30分钟真空蒸馏出易挥发物质,然后排放出产物,获得4951g粘的单相聚醚酯多元醇。产物具有以下的分析参数:
聚醚酯多元醇实施例C
将449.6g三羟甲基丙烷、3746.3g蓖麻油、250.0g Glissopal SA(购自BASF SE的分子量为1000g/mol的聚(异丁烯)琥珀酸酐)和1.5g咪唑初始进料至压力反应釜并在搅拌的同时用氮气惰化三次。然后将反应混合物加热至120℃并与于120分钟内加入的799.2g环氧丙烷混合。一旦单体加入完成且达到恒定反应压力,用氮气汽提约30分钟真空蒸馏出易挥发物质,然后排放出产物,获得4928.4g粘的、均质的、稍微浑浊的聚醚酯多元醇。产物具有以下的分析参数:
聚醚酯多元醇实施例D
将449.6g三羟甲基丙烷、3746.3g蓖麻油、250.0g Pentasize8(购自Trigon GmbH的C16/C18-烯基琥珀酸酐)和1.53g咪唑和0.053g叔丁醇Ti(IV)初始进料至压力反应釜并在搅拌的同时用氮气惰化三次。然后将反应混合物加热至120℃并与于120分钟内加入的801.1g环氧丙烷混合。一旦单体加入完成且达到恒定反应压力,用氮气汽提约30分钟真空蒸馏出易挥发物质,然后排放出产物,获得5140g粘的单相的聚醚酯多元醇。产物具有以下的分析参数:
聚醚酯多元醇实施例E
将1390.2g二丙二醇、1751.8g邻苯二甲酸酐、1004.2g大豆油和1.53g咪唑初始进料至压力反应釜并在搅拌的同时用氮气惰化三次。然后将反应混合物加热至120℃并与于120分钟内加入的855.8g环氧乙烷混合。一旦单体加入完成且达到恒定反应压力,用氮气汽提约30分钟真空蒸馏出易挥发物质,然后排放出产物,获得4914g粘的单相聚醚酯多元醇。产物具有以下的分析参数:
聚醚酯多元醇实施例F
将1101.0g二乙二醇、1749.5g邻苯二甲酸酐、1000.2g大豆油和1.5g咪唑初始进料至压力反应釜并在搅拌的同时用氮气惰化三次。然后将反应混合物加热至120℃并与于180分钟内加入的1150.6g环氧丙烷混合。一旦单体加入完成且达到恒定反应压力,用氮气汽提约30分钟真空蒸馏出易挥发物质,然后排放出产物,获得4940g粘的单相聚醚酯多元醇。产物具有以下的分析参数:
聚醚酯多元醇实施例G
将1108.9g蔗糖、336.3g甘油、233.9g蓖麻油、19.06g水、100gPentasize68(购自Trigon GmbH的C16/C18-烯基琥珀酸酐)和5.0g咪唑初始进料至压力反应釜并在搅拌的同时用氮气惰化三次。然后将反应混合物加热至130℃并与于7小时内加入的3306.3g环氧丙烷混合。一旦单体加入完成且达到恒定反应压力,用氮气汽提约30分钟真空蒸馏出易挥发物质,然后排放出产物,获得5014g粘的单相聚醚酯多元醇。产物具有以下的分析参数:
由这些实施例清楚可知,本发明的聚醚酯多元醇可通过简单的方法获得,并且所述方法产生了用于广泛应用的均一且均质的反应产物。
用途实施例1-2:涂料应用
制备用于机械测试的片材
在室温下存储和处理反应组分和添加剂。制备多元醇组分(组分A,见表)并在中混合2分钟。然后保持静置至少30分钟。计算异氰酸酯的加入量以使异氰酸酯指数为115.9。组分A与异氰酸酯在中混合60秒。将混合物倾入尺寸为30x20x0.2cm3的平滑的敞口模具中。所形成的片材在移出之前在模具中保持1小时。随后将所述片材在80℃下调节2小时。第二天,取适合的样本测定机械性能。
溶胀测试:
从尺寸为4x4cm2的样块切割出2mm的片材并称量以确定其质量(m1)。然后将样品放入充满水的6L桶中,将该桶在100℃下的加热箱中放置5小时。为防止样品向上漂移,将它们夹在金属框架上。移出样品之后,用纤维素稍微干燥并冷却至室温,测定质量(m2)并用[((m2-m1)/m1)x100%]来计算溶胀率,以百分比计。实验误差低于0.1%。测量值之间差异0.2%是显著的。
用途实施例1和2
异氰酸酯 LupranatM20S
指数 115.9
MV表示A至B组分的混合行为。
用途实施例1和2显示出,本发明的多元醇提供了具有常规涂料应用的性能的聚氨酯。
用途实施例3-4:硬质泡沫应用
制备用于机械测试的泡沫
部分水、部分戊烷发泡的聚异氰脲酸酯体系被视为碱性发泡体系。采用基于乙酸钾的催化剂以形成异氰脲酸酯基团。确定戊烷和水的量以使泡沫具有约31kg/m3的自由发泡密度;确定催化剂的量以使泡沫具有约50秒的凝胶时间。在室温下存储和处理反应组分和添加剂。
制备多元醇组分并使用实验室搅拌器手动搅拌。将组分A静置保持半小时,以使混合物中的大部分气泡可逃逸。计算异氰酸酯的加入量以使异氰酸酯指数为225。使用实验室搅拌器将组分A与异氰酸酯手动混合6秒。将混合物倾入相对于自由发泡密度过充10%的11L金属立方模具中,并且封闭模具。半小时之后,将立方泡沫脱模。在室温下储存泡沫样品3天,然后锯成测试样品用于机械测试。
用途实施例3和4显示出,本发明的多元醇提供了具有常规硬质泡沫表观密度和物理性能的硬质泡沫。
Claims (23)
1.一种制备聚醚酯多元醇的方法,所述方法借助亲核和/或碱性催化剂使混合物(A)与至少一种环氧烷v)反应,所述混合物(A)包含至少一种泽瓦夫活性化合物i),至少一种选自二羧酸的环状酸酐的化合物ii),至少一种脂肪酸酯iiib)以及任选地至少一种选自环状单酯和二酯的化合物iv),其中至少一种泽瓦夫活性化合物i)选自具有1至8的官能度的羟基和/或氨基官能的化合物,并且其中所述脂肪酸酯iiib)选自不含羟基的脂肪酸酯,及其混合物,其中亲核和/或碱性催化剂选自叔胺。
2.权利要求1的方法,其中在至少一种环氧烷v)加入之前,所述混合物(A)与亲核和/或碱性催化剂一起初始进料至反应容器中。
3.权利要求1或2的方法,其中所述二羧酸的环状酸酐ii)选自:a)烯基琥珀酸酐、b)邻苯二甲酸酐、c)马来酸酐、d)琥珀酸酐和e)四氢邻苯二甲酸酐,及其混合物。
4.权利要求3的方法,其中至少一种烯基琥珀酸酐a)选自C18-和/或C16-烯基琥珀酸酐、聚(异丁烯)琥珀酸酐及其混合物。
5.权利要求1或2的方法,其中至少一种环氧烷v)选自环氧丙烷、环氧乙烷、1,2-环氧丁烷、2,3-环氧丁烷、1,2-环氧戊烷、1-环氧辛烷、1-环氧癸烷、1-环氧十二烷、1-环氧十四烷、1-环氧十六烷、1-环氧十八烷、氧化苯乙烯、氧化环己烯、缩水甘油、表氯醇及其混合物。
6.权利要求1或2的方法,其中至少一种环氧烷v)选自环氧丙烷、环氧乙烷和环氧丁烷及其混合物。
7.权利要求1或2的方法,其中所述脂肪酸酯iiib)选自鲸骨脂、牛脂、大豆油、菜籽油、橄榄油、葵花籽油及其混合物。
8.权利要求1或2的方法,其中不存在所述化合物iv)。
9.权利要求1或2的方法,其中存在至少一种化合物iv)。
10.权利要求9的方法,其中至少一种化合物iv)选自γ-丁内酯、δ-戊内酯、ε-己内酯、(R,R)-丙交酯、(S,S)-丙交酯、内消旋丙交酯及其混合物。
11.权利要求9的方法,其中所述化合物iv)为ε-己内酯。
12.权利要求1或2的方法,其中碱性催化剂选自咪唑和咪唑衍生物。
13.权利要求1或2的方法,其中碱性催化剂选自咪唑。
14.权利要求1或2的方法,其中聚醚酯多元醇具有的羟值在20至1000mgKOH/g范围内。
15.权利要求1或2的方法,其中聚醚酯多元醇具有的羟值在100至600mgKOH/g范围内。
16.权利要求1或2的方法,其中聚醚酯多元醇包含5%至90重量%的衍生自脂肪酸酯iiib)的单元。
17.权利要求1或2的方法,其中聚醚酯多元醇包含5%至80重量%的衍生自化合物ii)的单元。
18.权利要求1或2的方法,其中与环氧烷v)的反应在80°至200℃的温度下进行。
19.权利要求1或2的方法,其作为半间歇法或连续法进行。
20.通过权利要求1至19任一项的方法获得的聚醚酯多元醇。
21.通过权利要求1至19任一项的方法获得的聚醚酯多元醇通过与二异氰酸酯或多异氰酸酯反应而制备发泡和/或致密聚氨酯的用途。
22.通过权利要求1至19任一项的方法获得的聚醚酯多元醇用于制备聚异氰脲酸酯泡沫的用途。
23.通过权利要求1至19任一项的方法获得的聚醚酯多元醇用于制备涂料或粘合剂领域的致密聚氨酯的用途。
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CN108017770A (zh) * | 2017-12-29 | 2018-05-11 | 浙江华峰合成树脂有限公司 | 无溶剂不黄变高透亮聚氨酯革用树脂及制法和应用 |
CN108467480A (zh) * | 2018-03-22 | 2018-08-31 | 上海联景高分子材料有限公司 | 聚醚改性聚酯多元醇及其聚合而成的热塑性聚氨酯弹性体 |
CN109456458A (zh) * | 2018-09-28 | 2019-03-12 | 山东诺威聚氨酯股份有限公司 | 用于鞋材的聚醚酯型tpu及其制备方法 |
FR3090672B1 (fr) | 2018-12-20 | 2021-10-15 | Bostik Sa | Composition à base de résine époxy et de polyuréthane |
WO2020165135A1 (en) | 2019-02-11 | 2020-08-20 | Basf Se | Acrylic copolymer capsule designed to open up at < 90°c for controlled release of in-situ forming pu/pir catalyst |
EP3838963A1 (de) | 2019-12-17 | 2021-06-23 | Covestro Deutschland AG | Verfahren zur herstellung von polyoxyalkylenpolyesterpolyolen |
WO2022158396A1 (ja) * | 2021-01-19 | 2022-07-28 | 東ソー株式会社 | ハロゲン含有ポリエーテルエステルポリオール |
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EP2807199B1 (de) | 2016-10-26 |
KR102085347B1 (ko) | 2020-03-05 |
EP2807199A1 (de) | 2014-12-03 |
BR112014017241A8 (pt) | 2017-07-04 |
ES2612313T3 (es) | 2017-05-16 |
JP2015506401A (ja) | 2015-03-02 |
RU2014134384A (ru) | 2016-03-20 |
KR20140127248A (ko) | 2014-11-03 |
MX2014007723A (es) | 2014-08-01 |
CN104066759A (zh) | 2014-09-24 |
HUE031526T2 (en) | 2017-07-28 |
SG11201404343VA (en) | 2014-10-30 |
EP2617748A1 (de) | 2013-07-24 |
WO2013110512A1 (de) | 2013-08-01 |
BR112014017241A2 (pt) | 2017-06-13 |
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