CN107406570A - 甲硅烷基化的聚氨酯、其制备和用途 - Google Patents
甲硅烷基化的聚氨酯、其制备和用途 Download PDFInfo
- Publication number
- CN107406570A CN107406570A CN201680014607.2A CN201680014607A CN107406570A CN 107406570 A CN107406570 A CN 107406570A CN 201680014607 A CN201680014607 A CN 201680014607A CN 107406570 A CN107406570 A CN 107406570A
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- CN
- China
- Prior art keywords
- carbon atom
- acid
- polyurethane
- silylated polyurethane
- alkyl
- 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
Links
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 43
- 239000004814 polyurethane Substances 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 28
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000000565 sealant Substances 0.000 claims abstract description 18
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical class [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000853 adhesive Substances 0.000 claims abstract description 16
- 230000001070 adhesive effect Effects 0.000 claims abstract description 16
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 239000008199 coating composition Substances 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000000962 organic group Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 5
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 15
- 239000000203 mixture Substances 0.000 claims description 56
- -1 hydroxypropyl Chemical group 0.000 claims description 50
- 229920000570 polyether Polymers 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 15
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 14
- 229910000077 silane Inorganic materials 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims description 6
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 claims description 5
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 claims description 3
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 claims description 2
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 claims description 2
- 150000004656 dimethylamines Chemical class 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- GXZZVJSQHUMLNV-UHFFFAOYSA-N methoxy-methyl-phenylsilane Chemical compound CO[SiH](C)C1=CC=CC=C1 GXZZVJSQHUMLNV-UHFFFAOYSA-N 0.000 claims description 2
- LGROXJWYRXANBB-UHFFFAOYSA-N trimethoxy(propan-2-yl)silane Chemical compound CO[Si](OC)(OC)C(C)C LGROXJWYRXANBB-UHFFFAOYSA-N 0.000 claims description 2
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 claims 1
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- 229920000642 polymer Polymers 0.000 description 27
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- 238000006243 chemical reaction Methods 0.000 description 16
- 150000007513 acids Chemical class 0.000 description 15
- 239000004014 plasticizer Substances 0.000 description 13
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 11
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- 239000002585 base Substances 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 10
- 239000000463 material Substances 0.000 description 10
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- 239000000945 filler Substances 0.000 description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 9
- 229920005862 polyol Polymers 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 229920004482 WACKER® Polymers 0.000 description 7
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 7
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
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- 238000001723 curing Methods 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- 229910052738 indium Inorganic materials 0.000 description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 6
- 229920006254 polymer film Polymers 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 229910052797 bismuth Inorganic materials 0.000 description 5
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 5
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- IJTNSXPMYKJZPR-UHFFFAOYSA-N parinaric acid Chemical compound CCC=CC=CC=CC=CCCCCCCCC(O)=O IJTNSXPMYKJZPR-UHFFFAOYSA-N 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
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- 235000012239 silicon dioxide Nutrition 0.000 description 5
- 238000007711 solidification Methods 0.000 description 5
- 230000008023 solidification Effects 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 4
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- 125000005369 trialkoxysilyl group Chemical group 0.000 description 4
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- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 3
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Abstract
本发明涉及一种甲硅烷基化的聚氨酯,其可通过包括以下步骤的方法获得:(a)使至少一种多元醇与至少一种三异氰酸酯反应以形成羟基封端的聚氨酯预聚物;和(b)使所述聚氨酯预聚物与至少一种式(1)的异氰酸基硅烷反应:OCN‑R‑Si‑(X)m(R1)3‑m (1)其中,m为0、1或2,各个R1彼此独立地为羟基、具有1~10个碳原子的烷氧基、具有1~10个碳原子的酰氧基或‑OCH(R2)COOR3,其中R2为氢或具有1~4个碳原子的烷基且R3是具有1~8个碳原子的直链或支化烷基,各个X彼此独立地为任选被取代的具有1~10个碳原子的烃基,其可以被至少一个杂原子间断,并且R是双官能有机基团,以用所述异氰酸基硅烷封端所述预聚物上的羟基。该甲硅烷基化的聚氨酯适合用于粘合剂、密封剂或涂料制剂中。
Description
技术领域
本发明涉及甲硅烷基化的聚氨酯、其制备及其用于粘合剂、密封剂和涂料组合物中的用途。
背景技术
具有反应性烷氧基甲硅烷基的聚合物体系是已知的。在大气水分的存在下,这些烷氧基硅烷封端的聚合物能够在室温下彼此缩合并释放烷氧基。在这种情况下,取决于烷氧基甲硅烷基的浓度及其构型,所形成的主要是长链聚合物(热塑性塑料)、相对宽网孔的三维网络(弹性体)或高度交联的体系(热固性塑料)。
聚合物通常包含末端带有烷氧基甲硅烷基的有机骨架。该有机骨架可以涉及例如聚氨酯、聚酯、聚醚等。
多年来,单组分湿固化粘合剂和密封剂在许多技术应用中发挥了重要作用。除了具有游离异氰酸酯基团的聚氨酯粘合剂和密封剂以及基于二甲基聚硅氧烷的传统有机硅粘合剂和密封剂之外,所谓的改性硅烷粘合剂和密封剂最近也越来越多地被使用。在后一组中,聚合物骨架的主要成分是聚醚,反应性的可交联端基是烷氧基甲硅烷基。与聚氨酯粘合剂和密封剂相比,改性硅烷粘合剂和密封剂具有不含异氰酸酯基团的优点,特别是不含有单体二异氰酸酯;它们也因对于未使用底漆进行表面预处理的多种基材而言具有较宽的粘附范围而著称。
US 4,222,925A和US 3,979,344A描述了硅氧烷封端的有机密封剂组合物,其在室温下可固化,基于以下反应的产物:异氰酸酯封端的聚氨酯预聚物与3-氨基丙基三甲氧基硅烷或2-氨基乙基甲氧基硅烷或3-氨基丙基甲氧基硅烷反应,以产生不含异氰酸酯的硅氧烷封端的预聚物。然而,基于这些预聚物的粘合剂和密封剂具有不令人满意的机械性能,特别是在其伸长率和断裂强度方面。
下面列出的基于聚醚的硅烷封端的预聚物的制备方法已有描述:
-不饱和单体与包含烷氧基甲硅烷基的单体(例如乙烯基三甲氧基硅烷)的共聚。
-将不饱和单体(例如乙烯基三甲氧基硅烷)接枝到热塑性塑料(例如聚乙烯)上。
-在醚合成中使用不饱和氯化合物(例如烯丙基氯)将羟基官能的聚醚转化为具有末端烯属双键的聚醚,其转而又在氢化硅烷化反应中于例如第8族过渡金属化合物的催化作用下与具有可水解基团的含氢硅烷化合物(例如HSi(OCH3)3)反应,得到硅烷封端的聚醚。
-在另一种方法中,含有烯属不饱和基团的聚醚与巯基硅烷(例如3-巯基丙基三烷氧基硅烷)反应。
-在还有一种方法中,首先将含羟基的聚醚与二异氰酸酯或多异氰酸酯反应,然后转而又与氨基官能的硅烷或巯基官能的硅烷反应,得到硅烷封端的预聚物。
-另有一种可能提供了羟基官能的聚醚与异氰酸基(isocyanato)官能的硅烷(例如3-异氰酸基丙基三甲氧基硅烷)的反应。
这些制备方法以及上述硅烷封端的预聚物用于粘合剂/密封剂应用中的用途记载在例如以下专利文献中:US 3,971,751A、EP-A-70475、DE-A-19849817、US 6,124,387A、US5,990,257A、US 4,960,844A、US 3,979,344A、US 3,632,557A、DE-A-4029504、EP-A-601021或EP-A-370464。
EP 0931800A1描述了通过以下过程制备甲硅烷基化的聚氨酯:使末端不饱和度小于0.02meq/g的多元醇组分与二异氰酸酯反应得到羟基封端的预聚物,然后使其与式OCN-R-Si-(X)m(-OR1)3-m的异氰酸基硅烷反应,其中m为0、1或2,并且各个R1残基为具有1~4个碳原子的烷基,R为双官能有机基团。根据该文献的教导,这种甲硅烷基化的聚氨酯表现出优异的机械性能组合,并且在合理的时间内固化以产生不表现出过大粘度的低粘性密封剂。
WO 2009/071542A1描述了一种制备甲硅烷基化的聚氨酯的方法,其包括使至少一种分子量为4,000~30,000g/mol的多元醇化合物和至少一种单官能化合物(对于异氰酸酯而言)与至少一种二异氰酸酯反应,其中所述一种或多种多元醇化合物和所述一种或多种单官能化合物的总量相对于所述一种或多种二异氰酸酯化合物化学计量过量,由此形成羟基封端的聚氨酯预聚物,所述聚氨酯预聚物随后与异氰酸基硅烷反应。
对于用于粘合剂和密封剂中的下述基于甲硅烷基化的聚氨酯的组合物仍存在需求:其表现出更好的性能,特别是固化速度和固化后的机械强度,并且同时显示出可接受的粘度,从而使得该组合物易于施用。因此,本发明的一个目的是提供具有改善的固化速度同时具有可接受的机械强度和粘度的甲硅烷基化的聚氨酯和相应的组合物。
发明内容
本发明实现其目的的方式可以从权利要求书中获得。其基本上包括甲硅烷基化的聚氨酯,所述甲硅烷基化的聚氨酯可通过包括以下步骤的方法获得:
(a)使至少一种多元醇与至少一种三异氰酸酯反应以形成羟基封端的聚氨酯预聚物;和
(b)使所述聚氨酯预聚物与至少一种式(1)的异氰酸基硅烷反应,
OCN-R-Si-(X)m(R1)3-m (1)
其中
m为0、1或2,
各个R1彼此独立地为羟基、具有1~10个碳原子的烷氧基、具有1~10个碳原子的酰氧基或-OCH(R2)COOR3,其中R2为氢或具有1~4个碳原子的烷基,R3是具有1~8个碳原子的直链或支化烷基,
各个X彼此独立地为任选被取代的具有1~10个碳原子的烃基,其可被至少一个杂原子间断,而且
R是双官能有机基团,
以用所述异氰酸基硅烷封端所述预聚物上的羟基。
根据本发明,通过使至少一种多元醇与至少一种三异氰酸酯反应,获得羟基封端的聚氨酯预聚物。
具体实施方式
出于本发明的目的,“多元醇”可理解为具有至少两个羟基的聚合物。原则上,作为多元醇化合物,可以使用多种带有至少两个羟基的聚合物,例如聚酯多元醇,聚己内酯,聚丁二烯或聚异戊二烯以及其氢化产物,或者也可以是聚丙烯酸酯或聚甲基丙烯酸酯。还可以使用不同多元醇化合物的混合物。
根据本发明,优选使用聚醚多元醇作为多元醇。出于本发明的目的,“聚醚”可理解为主链中重复单元含有醚官能团C-O-C的聚合物。因此,具有醚侧基的聚合物,例如纤维素醚、淀粉醚和乙烯基醚聚合物,以及聚缩醛未被该定义涵盖。
含有聚醚作为骨架的聚合物具有柔韧的弹性结构,使用其可以制备具有优异弹性性能的组合物。聚醚不仅骨架具有柔韧性,而且同时还强度较大。因此,例如,聚醚(与例如聚酯相比)不会受到水和细菌侵蚀或分解。
在本发明的优选实施方案中,多元醇是聚环氧烷烃,更优选聚环氧乙烷和/或聚环氧丙烷。
如果使用具有窄分子量分布且因此具有较低多分散性的聚醚作为聚合物骨架,则可以实现特别有利的粘弹性特性。这些物质可以例如通过所谓的双金属氰化物(DMC)催化来制备。以这种方式制备的聚醚因具有特别窄的分子量分布、高平均分子量和聚合物链末端处极少量的双键而著称。
在本发明的具体实施方案中,多元醇是多分散性PD小于3、优选小于1.7、更优选小于1.5、最优选小于1.3的聚醚多元醇。
根据本发明,多元醇化合物的聚合物骨架的数均分子量Mn为500~20,000g/mol(道尔顿)、优选2,000~18,000g/mol、最优选2,000~12,000g/mol,其末端不饱和度小于0.05meq/g、优选小于0.04meq/g、更优选小于0.02meq/g。
这些分子量是特别有利的,因为这些多元醇容易商购获得,并且所得的聚氨酯或基于其的组合物具有以下特性的良好平衡:在固化前的粘度(加工容易性)以及在固化后的强度和弹性。
数均分子量Mn以及重均分子量Mw通过凝胶渗透色谱法(GPC,也称为SEC)测定。该方法是本领域技术人员已知的。多分散性由平均分子量Mw和Mn获得。将其如下计算:PD=Mw/Mn。
比例Mw/Mn(也称为“多分散性”)表示分子量分布的宽度,因此表示多分散聚合物中各链的不同聚合度。对于许多聚合物和缩聚物,适用的多分散性值为约2。严格的单分散性将存在于值为1时。低多分散性(例如,小于1.5)表示相对较窄的分子量分布,因此表示与分子量相关的性质(如粘度)的特定表达。
适合于将多元醇化合物转化为羟基封端的聚氨酯预聚物的三异氰酸酯可以衍生自二异氰酸酯。优选地,三异氰酸酯衍生自HDI、TDI、MDI、PDI或IPDI,或它们的混合物。特别是,下述三异氰酸酯是最优选的。
根据本发明,使用一种或多种多元醇化合物的羟基相对于一种或多种三异氰酸酯或者三异氰酸酯混合物的NCO基团的化学计量过量。NCO基团与羟基的优选摩尔比为0.05~0.45,优选为0.1~0.45,更优选为0.2~0.45。这确保了本发明的步骤(a)中形成具有末端羟基的聚氨酯预聚物。
然后,使由此形成的具有末端羟基的聚氨酯预聚物与至少一种式(1)的异氰酸基硅烷反应:
OCN-R-Si-(X)m(R1)3-m,
以用所述异氰酸基硅烷封端所述预聚物上的羟基。
在式(1)中,m为0、1或2,优选为0或1。
各个R1彼此独立地为羟基、具有1~10个碳原子的烷氧基、具有1~10个碳原子的酰氧基或-OCH(R2)COOR3,其中R2为氢或具有1~4个碳原子的烷基,R3是具有1~8个碳原子的直链或支化烷基。
在本发明的优选实施方案中,各个R1彼此独立地为具有1~4个碳原子的烷氧基或酰氧基。更优选地,各个R1彼此独立地为甲氧基或乙氧基,特别是甲氧基。作为具有低立***阻(steric bulk)的相对较小的可水解基团,甲氧基和乙氧基是高反应性的,因此即使在以较低量使用催化剂时也能够快速固化。因此,对于需要快速固化的体系,例如在需要高初始粘合性的粘合剂中,它们特别受人关注。特别优选使用甲氧基。在烷氧基中甲氧基显示出最大的反应性。因此,当需要特别快速的固化时,可以使用这种类型的甲硅烷基。与甲氧基相比,较高级脂族残基例如乙氧基已经导致末端烷氧基甲硅烷基的反应性较低,并且可以有利地用于形成渐变式(gradual)交联速率。
在本发明的另一优选实施方案中,R1是-OCH(R2)COOR3,其中优选地R2是甲基且R3是具有1~4个碳原子的直链或支化烷基。
各个X彼此独立地是任选被取代的具有1~10个碳原子、更优选具有1~4个碳原子的烃基,其可被至少一个杂原子间断。“被至少一个杂原子间断”是指残基的主链包含至少一个与碳原子不同的原子作为链成员。优选地,各个X彼此独立地为具有1~10个碳原子的烷基,优选具有1~4个碳原子的烷基,特别优选甲基或乙基。
在本发明的优选实施方案中,式(1)中的m具有0或1的值,因此存在两个或三个羟基或可水解基团,优选烷氧基。通常,含有二烷氧基甲硅烷基或三烷氧基甲硅烷基的聚合物具有高反应性连接位点,这可实现快速固化、高交联度并因此可以具有良好的最终强度。二烷氧基甲硅烷基的特别的优点是相应的组合物在固化后比含有三烷氧基甲硅烷基的体系更软且更有弹性。因此,它们特别适合用作密封剂。此外,它们在固化时释放较少的醇,因此从生理学的角度也提供了应用优势。另一方面,使用三烷氧基甲硅烷基可以实现更高的交联度,这在固化后需要硬质固体物质时是特别有利的。此外,三烷氧基甲硅烷基更具反应性,即交联更快,因此减少了所需催化剂的量;并且它们在“冷塑(cold flow)”方面具有优势。
R是二官能有机基团,其可以是具有1~12个碳原子的烃基,优选具有1~6个碳原子的亚烷基,特别优选具有1~3个碳原子的亚烷基。更优选地,R是亚甲基、亚乙基或亚正丙基残基。特别优选使用亚甲基和亚正丙基残基。特别地,其中R为亚甲基的化合物在终止(terminating)甲硅烷基中表现出高反应性,这有助于缩短固化时间和硬化时间。如果R选择为亚丙基,则这些化合物表现出特别高的柔韧性。基于这些聚合物的配制物的固化速率还可以通过形成聚合物骨架与甲硅烷基残基之间的连接的烃残基的长度来影响。
以下列出的异氰酸基硅烷是特别合适的:
3-异氰酸基丙基三甲氧基硅烷、2-异氰酸基异丙基三甲氧基硅烷、4-异氰酸基-正丁基三甲氧基硅烷、2-异氰酸基-1,1-二甲基乙基三甲氧基硅烷、1-异氰酸基甲基三甲氧基硅烷、3-异氰酸基丙基三乙氧基硅烷、2-异氰酸基-2-甲基乙基三乙氧基硅烷、4-异氰酸基丁基三乙氧基硅烷、2-异氰酸基-1,1-二甲基乙基三乙氧基硅烷、1-异氰酸基甲基三乙氧基硅烷、3-异氰酸基丙基甲基二甲氧基硅烷、3-异氰酸基丙基二甲基甲氧基硅烷、3-异氰酸基丙基苯基甲基甲氧基硅烷、1-异氰酸基甲基甲基二甲氧基硅烷、3-异氰酸基丙基乙基二乙氧基硅烷、3-异氰酸基丙基甲基二乙氧基硅烷、1-异氰酸基甲基甲基二乙氧基硅烷及其混合物。
更特别优选的是3-异氰酸基丙基三甲氧基硅烷、3-异氰酸基丙基三乙氧基硅烷、1-异氰酸基甲基三乙氧基硅烷、3-异氰酸基丙基甲基二甲氧基硅烷、1-异氰酸基甲基甲基二甲氧基硅烷、1-异氰酸基甲基甲基二乙氧基硅烷及其混合物。
在本发明的具体实施方案中,上述制备甲硅烷基化的聚氨酯的方法包括添加催化剂的另一步骤。合适的催化剂是公知的。原则上,可以使用任何可以催化羟基与异氰酸基的反应形成氨基甲酸酯键的化合物。其实例包括:锡化合物,例如锡羧酸盐,如二月桂酸二丁基锡(DBTL)、二乙酸二丁基锡、二乙基己酸二丁基锡、二辛酸二丁基锡、二甲基马来酸二丁基锡、二乙基马来酸二丁基锡、二丁基马来酸二丁基锡、二异辛基马来酸二丁基锡、二(十三烷基)马来酸二丁基锡、二苄基马来酸二丁基锡、马来酸二丁基锡、二乙酸二丁基锡、辛酸锡、二硬脂酸二辛基锡、二月桂酸二辛基锡(DOTL)、二乙基马来酸二辛基锡、二异辛基马来酸二辛基锡、二乙酸二辛基锡和环烷酸锡;锡醇盐,如二甲醇二丁基锡、二苯酚二丁基锡和二异丙醇二丁基锡;锡氧化物,如二丁基氧化锡和二辛基氧化锡;二丁基氧化锡与邻苯二甲酸酯之间的反应产物,双乙酰丙酮二丁基锡;以及非锡化合物。后者包括:钛酸酯,如钛酸四丁酯和钛酸四丙酯;有机铝化合物,如三乙酰丙酮铝、三乙基乙酰乙酸铝和乙基乙酰乙酸二异丙氧基铝;螯合化合物,如四乙酰丙酮锆和四乙酰丙酮钛;辛酸铅;胺化合物或其与羧酸的盐,如丁胺、辛胺、月桂胺、二丁胺、单乙醇胺、二乙醇胺、三乙醇胺、二亚乙基三胺、三亚乙基四胺、油胺、环己胺、苄胺、二乙基氨基丙胺、苯二甲胺、三亚乙基二胺、胍、二苯基胍、2,4,6-三(二甲基氨基甲基)苯酚、吗啉、N-甲基吗啉、2-乙基-4-甲基咪唑和1,8-二氮杂双环-(5,4,0)-十一碳烯-7(DBU),由过量的多胺和多元酸获得的低分子量聚酰胺树脂,过量的多胺与环氧树脂的加成物,具有氨基的硅烷粘合促进剂,例如3-氨基丙基三甲氧基硅烷和N-(β-氨基乙基)氨基丙基甲基二甲氧基硅烷,以及钾、铁、铟、锌、铋和铜的化合物,优选钾、铁、铟、锌、铋或铜的羧酸盐(脂肪族羧酸的盐)或乙酰丙酮化物。优选地,催化剂选自钾、铁、铟、锌、铋和铜的化合物,优选钾、铁、铟、锌、铋或铜的羧酸盐(脂肪族羧酸的盐)或乙酰丙酮化物。可以使用C4~C36饱和的、单不饱和的或多不饱和的一元羧酸,特别是脂肪族羧酸。其实例是:花生酸(正二十烷酸)、花生四烯酸(全顺式-5,8,11,14-二十碳四烯酸)、山萮酸(二十二烷酸)、酪酸(丁酸)、癸烯酸(9-癸烯酸)、羊蜡酸(正癸酸)、己酸(正己酸)、辛酸(正辛酸)、蜡酸(二十六烷酸)、鲸蜡烯酸(顺式-11-二十二碳烯酸)、鰶鱼酸(全顺式-7,10,13,16,19-二十二碳五烯酸)、桐酸(反式-9-反式-11-顺式-13-十八碳-9,11,13-三烯酸)、庚酸(1-己烷甲酸)、芥酸(顺式-13-二十二碳烯酸)、鳕油酸(9-二十碳烯酸)、巨头鲸鱼酸(顺式-11-二十碳烯酸)、十六碳三烯酸(hiragonic acid)(6,10,14-十六碳三烯酸)、月桂酸(十二烷酸)、木蜡酸(二十四烷酸)、天台乌药酸(顺式-4-十二碳烯酸)、亚油酸((顺式,顺式)-十八碳-9,12-二烯酸)、亚麻酸((全顺式)-十八碳-9,12,15-三烯酸)、蜂花酸(三十烷酸)、褐煤酸(二十八烷酸)、十八碳四烯酸(stearidonic acid)(顺式-6-顺式-9-顺式-12-顺式-15-十八碳四烯酸)、肉豆蔻酸(十四烷酸)、肉豆蔻烯酸(顺式-9-十四碳烯酸)、环烷酸、新癸酸、三桠酸(顺式-4-癸烯酸)、辛酸(正辛酸)、新辛酸、油酸(顺式-9-十八碳烯酸)、棕榈酸(正十六烷酸)、棕榈油酸(顺式-9-十六碳烯酸)、帕里拉油酸(9,11,13,15-十八碳四烯酸)、岩芹酸(顺式-6-十八碳烯酸)、抹香鲸酸(5-十四碳烯酸)、石榴酸(顺式-9-反式-11-顺式-13-十八碳-9,11,13-三烯酸)、斜齿鲨酸(顺式-5-顺式-11-顺式-14-二十碳三烯酸)、鲨鱼油酸(15-二十四碳烯酸)、硬脂酸(正十八烷酸)、二十三烷酸、粗租酸(顺式-4-十四碳烯酸)、反式-异油酸(反式-11-十八碳烯酸)、棕榈油酸(9-十六碳烯酸)。除了乙酰丙酮化物之外,还可以使用钾、铁、铟、锌、铋或铜的其它β-二羰基化合物的螯合物。具体地可以列举出乙酰乙酸烷基酯、丙二酸二烷基酯、苯甲酰基乙酸酯、二苯甲酰甲烷、苯甲酰丙酮和脱氢乙酰乙酸。
本发明还提供了一种制备甲硅烷基化的聚氨酯的方法,其包括以下步骤:
(a)使至少一种多元醇与至少一种三异氰酸酯反应以形成羟基封端的聚氨酯预聚物;和
(b)使所述聚氨酯预聚物与至少一种式(1)的异氰酸基硅烷反应
OCN-R-Si-(X)m(R1)3-m (1)
其中
m为0、1或2,
各个R1彼此独立地为羟基、具有1~10个碳原子的烷氧基、具有1~10个碳原子的酰氧基或-OCH(R2)COOR3,其中R2为氢或具有1~4个碳原子的烷基,R3是具有1~8个碳原子的直链或支化烷基,
各个X彼此独立地为任选被取代的具有1~10个碳原子的烃基,其可被至少一个杂原子间断,并且
R是双官能有机基团,
以用所述异氰酸基硅烷封端所述预聚物上的羟基。
因此,本发明的针对甲硅烷基化的聚氨酯描述的一般的、优选的和特别优选的实施方案也适用于本发明的制备甲硅烷基化的聚氨酯的方法。
本发明还提供一种可固化组合物,特别是包含至少一种本发明的甲硅烷基化的聚氨酯或可通过本发明的上述方法获得的甲硅烷基化的聚氨酯的粘合剂、密封剂或涂料组合物。
除了本发明的上述甲硅烷基化的聚氨酯之外,本发明的粘合剂、密封剂、涂料组合物还可以含有赋予这些粘合剂、密封剂、涂料组合物改进的弹性特性、改进的弹性回复性、足够长的处理时间、快速固化时间和低残留粘性的其它助剂和添加剂。这些助剂和添加剂中包括例如催化剂、增塑剂、稳定剂、抗氧化剂、填料、反应性稀释剂、干燥剂、粘合促进剂和UV稳定剂、杀菌剂、阻燃剂、流变助剂、着色颜料或染料糊,且/或任选地还包含少量的溶剂。
“增塑剂”可理解为降低组合物的粘度并因此有助于加工性能的物质。增塑剂优选选自脂肪酸酯、二羧酸酯、携带OH基团的或环氧化的脂肪酸的酯、脂肪、乙醇酸酯、苯甲酸酯、磷酸酯、磺酸酯、偏苯三酸酯、环氧化增塑剂、聚醚增塑剂、聚苯乙烯、烃类增塑剂和氯化石蜡,以及其两种以上的混合物。对这些增塑剂之一或特定组合的针对性选择不仅可以使粘度降低从而得到更好的加工性能,而且还可以得到本发明组合物的另外的有利性质,例如聚合物的胶凝能力、低温弹性和/或低温强度,或甚至抗静电性。
原则上,可以使用邻苯二甲酸酯作为增塑剂。然而,由于其潜在的毒性,这些酯不是优选的。
在聚醚增塑剂中,优选使用封端的聚乙二醇,例如聚乙二醇或聚丙二醇二C1-4烷基醚,特别是二乙二醇或二丙二醇的二甲基或二乙基醚,以及其两种以上的混合物。还适合作为增塑剂的是例如松香酸的酯、丁酸酯、乙酸酯、丙酸酯、硫代丁酸酯、柠檬酸酯以及基于硝化纤维素和聚乙酸乙烯酯的酯,以及其两种以上的混合物。还适合的是,例如己二酸单辛酯与2-乙基己醇的不对称酯(Edenol DOA,Cognis Deutschland GmbH,)。单官能的线性或支化C4-16醇的纯醚或混合醚,或这些醇的两种以上不同醚的混合物如二辛醚(可作为Cetiol OE,从Cognis Deutschland GmbH,获得)也适合作为增塑剂。在本发明的情形中同样适合用作增塑剂的是二氨基甲酸酯(diurethane),其可以例如通过以下方式制备:通过使具有OH端基的二醇与单官能异氰酸酯反应,通过选择化学计量使得基本上所有的游离OH基团完全反应。制备二氨基甲酸酯的另一种方法包括使单官能醇与二异氰酸酯反应,从而使得所有NCO基团尽可能完全反应。
基于组合物的总重量,增塑剂可以以0~40重量%、优选0~20重量%额外用于组合物中。
用于本发明目的的“稳定剂”可理解为抗氧化剂、UV稳定剂或水解稳定剂。其实例是商业上常见的空间位阻酚和/或硫醚,以及或者受阻胺光稳定剂(HALS)类型的被取代的苯并***和/或胺。本发明的情形中优选的是使用带有甲硅烷基并且在交联或固化后结合到最终产物中的UV稳定剂。产品Lowilite 75、Lowilite 77(Great Lakes,USA)特别适合此目的。还可以添加苯并***、二苯甲酮、苯甲酸酯、氰基丙烯酸酯、丙烯酸酯、空间位阻酚、磷和/或硫。
本发明的组合物可以含有至多约2重量%、优选约1重量%的稳定剂。此外,本发明的组合物还可以含有至多约7重量%、特别是至多约5重量%的抗氧化剂。
可以使用的催化剂是能够催化硅烷类(grouping)的可水解基团的水解裂解以及随后的Si-OH基团缩合以产生硅氧烷类(交联反应和粘合促进功能)的所有已知化合物。其实例为:钛酸酯,如钛酸四丁酯和钛酸四丙酯;锡羧酸盐,如二月桂酸二丁基锡(DBTL)、二乙酸二丁基锡、二乙基己酸二丁基锡、二辛酸二丁基锡、二甲基马来酸二丁基锡、二乙基马来酸二丁基锡、二丁基马来酸二丁基锡、二异辛基马来酸二丁基锡、二(十三烷基)马来酸二丁基锡、二苄基马来酸二丁基锡、马来酸二丁基锡、二乙酸二丁基锡、辛酸锡、二硬脂酸二辛基锡、二月桂酸二辛基锡(DOTL)、二乙基马来酸二辛基锡、二异辛基马来酸二辛基锡、二乙酸二辛基锡和环烷酸锡;锡醇盐,如二甲醇二丁基锡、二苯酚二丁基锡和二异丙醇二丁基锡;锡氧化物,如二丁基氧化锡和二辛基氧化锡;二丁基氧化锡和邻苯二甲酸酯之间的反应产物,双乙酰丙酮二丁基锡;有机铝化合物,如三乙酰丙酮铝、三乙基乙酰乙酸铝和乙基乙酰乙酸二异丙氧基铝;螯合化合物,如四乙酰丙酮锆和四乙酰丙酮钛;辛酸铅;胺化合物或其与羧酸的盐,如丁胺、辛胺、月桂胺、二丁胺、单乙醇胺、二乙醇胺、三乙醇胺、二亚乙基三胺、三亚乙基四胺、油胺、环己胺、苄胺、二乙基氨基丙胺、苯二甲胺、三亚乙基二胺、胍、二苯基胍、2,4,6-三(二甲基氨基甲基)苯酚、吗啉、N-甲基吗啉、2-乙基-4-甲基咪唑和1,8-二氮杂双环-(5,4,0)-十一碳烯-7(DBU),由过量的多胺和多元酸获得的低分子量聚酰胺树脂,过量的多胺与环氧树脂的加成物,具有氨基的硅烷粘合促进剂,例如3-氨基丙基三甲氧基硅烷和N-(β-氨基乙基)氨基丙基甲基二甲氧基硅烷。
基于组合物的总重量,催化剂——优选几种催化剂的混合物——可以以0.01~约5重量%的量使用。
本发明的组合物可另外含有填料。此处合适的是例如白垩、石灰粉、沉淀硅酸和/或热解硅酸、沸石、膨润土、碳酸镁、硅藻土、氧化铝、粘土、滑石、二氧化钛、氧化铁、氧化锌、砂、石英、燧石、云母、玻璃粉和其它研磨的矿物。还可以使用有机填料,特别是炭黑、石墨、木纤维、木粉、锯屑、纤维素、棉、纸浆、棉、木屑、切碎的秸秆(chopped straw)、谷壳、研磨的胡桃壳和其它短切纤维。还可以加入短纤维,如玻璃纤维、玻璃丝、聚丙烯腈、碳纤维、Kevlar纤维或聚乙烯纤维。铝粉同样适合用作填料。
热解硅酸和/或沉淀硅酸的BET表面积有利地为10~90m2/g。当使用它们时,其不会引起本发明的组合物的粘度的任何额外增加,却有助于增强经固化的组合物。
同样可以想到,使用具有较高的BET表面积、有利地为100~250m2/g、特别是110~170m2/g的热解硅酸和/或沉淀硅酸作为填料。由于BET表面积较大,因此可利用较小重量比的硅酸实现相同的效果,例如增强经固化的组合物。因此,根据不同需求,可以使用其它物质来改善本发明的组合物。
还适合作为填料的是具有矿物壳或塑料壳的空心球。这些空心球可以是例如可以商品名Glass 购得的空心玻璃球。基于塑料的空心球、例如或描述于例如EP 0 520 426B1中。它们由无机物质或有机物质组成,每个空心球的直径为1mm以下、优选500μm以下。
赋予组合物触变性的填料对于许多应用是优选的。这种填料也被描述为流变助剂,例如氢化蓖麻油、脂肪酸酰胺或可溶胀塑料如PVC。为了容易地从合适的分配装置(例如管)中挤出,这种组合物具有3000~150,000mPas、优选40,000~80,000mPas、或甚至50,000~60,000mPas的粘度。
基于组合物的总重量,填料可优选以1~80重量%、优选5~60重量%的量使用。
合适的颜料的实例是二氧化钛、铁氧化物或炭黑。
为了更进一步提高储存期限,常常可取的是使用干燥剂进一步使本发明的组合物相对于水分渗透稳定。有时还需要通过使用反应性稀释剂来降低本发明的粘合剂或密封剂的粘度,以用于特定应用。可以使用可与粘合剂或密封剂混溶而降低粘度的和具有至少一个对粘合剂具有反应性的基团的所有化合物作为反应性稀释剂。
作为反应性稀释剂,例如可以使用以下物质:与异氰酸基硅烷反应的聚亚烷基二醇(例如Synalox 100-50B,Dow)、氨基甲酸基丙基三甲氧基硅烷(carbamatopropyltrimethoxysilane)、烷基三甲氧基硅烷、烷基三乙氧基硅烷、甲基三甲氧基硅烷、甲基三乙氧基硅烷和乙烯基三甲氧基硅烷(VTMO Geniosil XL 10,Wacker)、乙烯基三乙氧基硅烷、苯基三甲氧基硅烷、苯基三乙氧基硅烷、辛基三甲氧基硅烷、四乙氧基硅烷、乙烯基二甲氧基甲基硅烷(XL12,Wacker)、乙烯基三乙氧基硅烷(GF56,Wacker)、乙烯基三乙酰氧基硅烷(GF62,Wacker)、异辛基三甲氧基硅烷(IO Trimethoxy)、异辛基三乙基硅烷(IO Triethoxy,Wacker)、氨基甲酸N-三甲氧基甲硅烷基甲基-O-甲基酯(XL63,Wacker)、氨基甲酸N-二甲氧基(甲基)甲硅烷基甲基-O-甲基酯(XL65,Wacker)、十六烷基三甲氧基硅烷、3-辛酰基硫基-1-丙基三乙氧基硅烷和上述化合物的部分水解产物。
还可用作反应性稀释剂的是Kaneka Corp.的以下聚合物:MS S203H、MS S303H、MSSAT 010和MS SAX 350。
同样可以使用衍生自例如异氰酸基硅烷与Synalox牌号物质(grade)的反应的硅烷改性聚合物。
以相同的方式,本发明的甲硅烷基化的聚氨酯可以与本身已知的常规聚合物或预聚物一起在混合物中使用,任选地同时使用上述反应性稀释剂、填料以及其它助剂和添加剂。“常规聚合物或预聚物”在这种情况下可以选自聚酯、聚氧化亚烷基、聚丙烯酸酯、聚甲基丙烯酸酯或其混合物;这些物质可以不含对硅氧烷基团具有反应性的基团,但任选地也可以包含烷氧基甲硅烷基或羟基。
多种上述具有硅烷官能团的反应性稀释剂在组合物中同时具有干燥和/或促进粘合的效果。基于组合物的总重量,这些反应性稀释剂的用量可以为0.1~15重量%,优选为1~5重量%。
然而,还适合作为粘合促进剂的是所谓的增粘剂,例如烃树脂、酚树脂、萜烯-酚醛树脂、间苯二酚树脂或其衍生物、改性的或未改性的树脂酸或树脂酯(松香酸衍生物)、聚胺、聚氨基酰胺、酸酐和含酸酐的共聚物。少量添加聚环氧化物树脂也可以改善在许多基材上的粘合性。出于该原因则优选使用细磨形式的分子量超过700的固体环氧树脂。如果使用增粘剂作为粘合促进剂,其性质和数量取决于粘合剂/密封剂组合物和其所施加的基材。通常的增粘树脂(增粘剂)——例如萜烯-酚醛树脂或树脂酸衍生物——可以以5~20重量%的浓度使用;基于组合物的总重量,通常的粘合促进剂——例如聚胺、聚氨基酰胺或酚醛树脂或间苯二酚衍生物——可以以0.1~10重量%使用。
本发明还提供了本发明的甲硅烷基化的聚氨酯作为粘合剂、密封剂、涂料组合物的用途,或用于制备粘合剂、密封剂、涂料组合物的用途。
原则上,在本发明中,在本文上下文中列举的所有特征——特别是本发明的组合物、本发明的方法和本发明的用途的被认为优选的和/或特殊的实施方案、比例范围、组分和其它特征——可以以所有可能的且不相互排斥的组合来实现,其中被认为优选的和/或特殊的特征的组合也被认为是优选的和/或特殊的。
实施例
实施例(Ex 1)
-甲硅烷基化的聚氨酯的制备(使用三异氰酸酯):
将384.02g(33.88mmol)聚丙烯醚多元醇(Acclaim 12200,羟基值=9.90)在真空下于80~90℃的500ml三颈烧瓶中干燥。在氮气氛下,在搅拌下加入0.28g新戊酸铋(BorchiKat 315)。然后,在搅拌下加入2.52g(4.52mmol)三异氰酸酯(Tolonate HDT-LV)(NCO/OH比=0.2)。将混合物在80~95℃下放置1小时。用NCO监测完成转化;一旦经滴定达到预聚物的理论NCO值(%NCO=0),即在搅拌下加入13.18g(62.69mmol)3-异氰酸基丙基三甲氧基硅烷(Geniosil GF 40),并将混合物在80~95℃下再放置一小时(%NCO=0.00至0.09)。得到星形聚合物。将所得聚合物在氮气氛下储存在防潮玻璃容器中,然后进一步加工成可固化组合物。粘度为41,200mPas。
比较例1(Comp 1)
-甲硅烷基化的聚氨酯的制备(使用二异氰酸酯):
进行与实施例1类似的工序,不同之处在于使用HDI代替三异氰酸酯。粘度为28,200mPas。细节总结在表1中。
实施例2(Ex 2)
-甲硅烷基化的聚氨酯的制备(使用三异氰酸酯):
进行与实施例1类似的工序,不同之处在于NCO/OH比=0.4,并且使用Acclaim4200(羟基值=29.50)代替Acclaim 12200。粘度为78,600mPas。细节总结在表1中。
比较例2(Comp 2)
-甲硅烷基化的聚氨酯的制备(使用二异氰酸酯):
进行与实施例2类似的工序,不同之处在于使用HDI代替三异氰酸酯。粘度为10,600mPas。细节总结在表1中。
表1
聚合物粘度的测定:
使用Brookfield粘度计(DV-II+Pro)、转子7、20rpm在23℃测定粘度值。
实施例A~F
-包含甲硅烷基化的聚氨酯的组合物的制备:
将上述实施例的各个所制备的甲硅烷基化的聚氨酯在23℃下加热24小时,然后将0.35g N-(2-氨基乙基)-3-氨基丙基三甲氧基硅烷(Geniosil GF91)和0.14g DOTL或DBU加入到34.51g各个所制备的聚合物中。将该混合物在SpeedMixer(DAC 150FC)中以2700rpm均化60秒,进行两次。
对于上述混合物,确定形成表皮(skin)的时间(表干时间(Skin over Time)/SOT)和机械强度(拉伸强度和伸长率)。结果总结在下表2中。在制备实施例A~D时使用DOTL,并且在制备实施例E~F时使用DBU作为不含锡的催化剂。
表2
表干时间(SOT)和机械强度(拉伸强度和伸长率)的测定:
将上述混合物均化并施加在框架(50×130×2mm)中。将各个混合物均匀分布,从而使得所述框架可以被完全填充。由此得到薄聚合物膜。对于这些组合物,使用末端具有圆形刮刀的工具(150×5mm)来确定形成表皮的时间(表干时间/SOT)。将刮刀的末端每1~5分钟与聚合物膜的表面轻轻接触,并小心地移除。一旦在将刮刀从聚合物膜的表面上移除时不会再有配制物残渣残留在刮刀上,则测量SOT。然后,必须将所得到的线(string)从刮刀中移除而无残留。聚合物膜回到其原来的形状。在检查SOT时,每次必须使用聚合物膜表面的不同部分。测试在23℃和50%相对湿度下进行。
储存7天(23℃,相对湿度50%)后,由聚合物膜制备4个试样,并将其根据DIN53504-S3A使用压机(APK T3-5-40)和打孔工具单元打孔。机械数据参照DIN53504:2009-10确定。使用0.05MPa的预荷载和40mm/分钟的速度将各个试样设定在初始试验位置。实际测量使用速度50mm/分钟进行。
实施例表明,含有本发明的甲硅烷基化的聚氨酯(实施例1~2)的混合物A、C和E表现出合理的粘度,显示出比包含比较例1~2的甲硅烷基化的聚氨酯的混合物明显更短的SOT,同时具有良好的机械强度(拉伸强度和伸长率)。此外,实施例E和F的比较表明,即使在使用非锡催化剂的情况下,含有本发明的甲硅烷基化的聚氨酯的混合物也显示出较短的SOT和良好的机械性能。
Claims (10)
1.甲硅烷基化的聚氨酯,其可通过包括以下步骤的方法获得:
(a)使至少一种多元醇与至少一种三异氰酸酯反应以形成羟基封端的聚氨酯预聚物;和
(b)使所述聚氨酯预聚物与至少一种式(1)的异氰酸基硅烷反应
OCN-R-Si-(X)m(R1)3-m (1)
其中
m为0、1或2,
各个R1彼此独立地为羟基、具有1~10个碳原子的烷氧基、具有1~10个碳原子的酰氧基或-OCH(R2)COOR3,其中R2为氢或具有1~4个碳原子的烷基,且R3是具有1~8个碳原子的直链或支化烷基,
各个X彼此独立地为任选被取代的具有1~10个碳原子的烃基,其可被至少一个杂原子间断,并且
R是双官能有机基团,
以用所述异氰酸基硅烷封端所述预聚物上的羟基。
2.如权利要求1所述的甲硅烷基化的聚氨酯,其中所述三异氰酸酯的NCO基团与所述多元醇的羟基的摩尔比为0.05~0.45、优选0.1~0.45、更优选0.2~0.45。
3.如前述权利要求中至少一项所述的甲硅烷基化的聚氨酯,其中所述多元醇是聚醚多元醇。
4.如前述权利要求中至少一项所述的甲硅烷基化的聚氨酯,其中所述多元醇的数均分子量为500~20,000g/mol、优选1,000~20,000g/mol、更优选2,000~18,000g/mol、最优选2,000~12,000g/mol。
5.如前述权利要求中至少一项所述的甲硅烷基化的聚氨酯,其中所述三异氰酸酯衍生自HDI、TDI、MDI、PDI、IPDI或它们的混合物。
6.如前述权利要求中至少一项所述的甲硅烷基化的聚氨酯,其中所述异氰酸基硅烷选自3-异氰酸基丙基三甲氧基硅烷、2-异氰酸基异丙基三甲氧基硅烷、4-异氰酸基-正丁基三甲氧基硅烷、2-异氰酸基-1,1-二甲基乙基三甲氧基硅烷、1-异氰酸基甲基三甲氧基硅烷、3-异氰酸基丙基三乙氧基硅烷、2-异氰酸基-2-甲基乙基三乙氧基硅烷、4-异氰酸基丁基三乙氧基硅烷、2-异氰酸基-1,1-二甲基乙基三乙氧基硅烷、1-异氰酸基甲基三乙氧基硅烷、3-异氰酸基丙基甲基二甲氧基硅烷、3-异氰酸基丙基二甲基甲氧基硅烷、3-异氰酸基丙基苯基甲基甲氧基硅烷、1-异氰酸基甲基甲基二甲氧基硅烷、3-异氰酸基丙基乙基二乙氧基硅烷、3-异氰酸基丙基甲基二乙氧基硅烷、1-异氰酸基甲基甲基二乙氧基硅烷及它们的混合物。
7.如前述权利要求中至少一项所述的甲硅烷基化的聚氨酯,其中所述方法包括另一步骤:添加催化剂。
8.制备甲硅烷基化的聚氨酯的方法,其包括以下步骤:
(a)使至少一种多元醇与至少一种三异氰酸酯反应以形成羟基封端的聚氨酯预聚物;和
(b)使所述聚氨酯预聚物与至少一种式(1)的异氰酸基硅烷反应
OCN-R-Si-(X)m(R1)3-m (1)
其中
m为0、1或2,
各个R1彼此独立地为羟基、具有1~10个碳原子的烷氧基、具有1~10个碳原子的酰氧基或-OCH(R2)COOR3,其中R2为氢或具有1~4个碳原子的烷基,R3是具有1~8个碳原子的直链或支化烷基,
各个X彼此独立地为任选被取代的具有1~10个碳原子的烃基,其可被至少一个杂原子间断,而且
R是双官能有机基团,
以用所述异氰酸基硅烷封端所述预聚物上的羟基。
9.粘合剂、密封剂或涂料组合物,其包含权利要求1~7中至少一项所述的甲硅烷基化的聚氨酯。
10.权利要求1~7中至少一项所述的甲硅烷基化的聚氨酯作为粘合剂、密封剂或涂料组合物的用途,或者用于制备粘合剂、密封剂或涂料组合物的用途。
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- 2015-03-11 PL PL15158615T patent/PL3067375T3/pl unknown
- 2015-03-11 ES ES15158615.3T patent/ES2645863T3/es active Active
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2016
- 2016-03-09 CN CN201680014607.2A patent/CN107406570B/zh not_active Expired - Fee Related
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- 2016-03-09 BR BR112017017856A patent/BR112017017856A2/pt not_active Application Discontinuation
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- 2016-03-09 WO PCT/EP2016/055005 patent/WO2016142416A1/en active Application Filing
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- 2017-09-07 US US15/697,499 patent/US10118984B2/en active Active
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CN111978850A (zh) * | 2020-07-22 | 2020-11-24 | 上海三棵树防水技术有限公司 | 一种硅烷改性防水涂料及其制备方法 |
Also Published As
Publication number | Publication date |
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CA2978978A1 (en) | 2016-09-15 |
EP3067375B1 (en) | 2017-08-30 |
PL3067375T3 (pl) | 2018-01-31 |
WO2016142416A1 (en) | 2016-09-15 |
MX2017011530A (es) | 2017-12-14 |
CA2978978C (en) | 2023-07-04 |
RU2690688C2 (ru) | 2019-06-05 |
RU2017134961A3 (zh) | 2019-04-23 |
RU2017134961A (ru) | 2019-04-05 |
CN107406570B (zh) | 2021-02-19 |
JP6867294B2 (ja) | 2021-04-28 |
CL2017002261A1 (es) | 2018-04-20 |
US10118984B2 (en) | 2018-11-06 |
EP3067375A1 (en) | 2016-09-14 |
ES2645863T3 (es) | 2017-12-11 |
KR20170128418A (ko) | 2017-11-22 |
BR112017017856A2 (pt) | 2018-04-10 |
US20170362371A1 (en) | 2017-12-21 |
JP2018513232A (ja) | 2018-05-24 |
US20190031812A1 (en) | 2019-01-31 |
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