CN111051378A - 新型低聚物或聚合物以及包含其的组合物 - Google Patents

新型低聚物或聚合物以及包含其的组合物 Download PDF

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CN111051378A
CN111051378A CN201880056107.4A CN201880056107A CN111051378A CN 111051378 A CN111051378 A CN 111051378A CN 201880056107 A CN201880056107 A CN 201880056107A CN 111051378 A CN111051378 A CN 111051378A
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oligomer
diisocyanate
mono
composition according
polymer
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S·伦达克
P·温纳伯格
D·詹姆斯
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Perstorp AB
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Abstract

本发明公开了通过使至少一种具有两个或更多个异氰酸酯基团的单体、低聚或聚合异氰酸酯与2‑羟基‑3‑丁烯酸和/或2‑羟基‑3‑丁烯酸的至少一种烷基酯反应而获得的低聚物或聚合物。还公开了包含所述低聚物或聚合物的组合物。

Description

新型低聚物或聚合物以及包含其的组合物
技术领域
本发明涉及通过使至少一种具有两个或更多个异氰酸酯基团的单体、低聚或聚合异氰酸酯与2-羟基-3-丁烯酸和/或2-羟基-3-丁烯酸的至少一种烷基酯反应而获得的新型低聚物或聚合物。
背景技术
具有一个或多个碳-碳双键(不饱和键)的化学化合物是本领域众所周知的，并且在广泛多样的应用中用作反应物和化学构件块，例如干燥和/或热固化和/或UV、IR和EB固化涂料、釉质、油灰、漆、清漆、粘合剂和油墨、酯和聚酯、胶乳、纤维、纺织品等等，以及例如用于模制和浇铸组合物等等。然而，尽管存在大量商购可得的不饱和化合物及其衍生物，但由于例如环境问题和法规和/或新的应用领域，对于具有一个或多个碳-碳双键的新型、更安全、更有效和/或更通用的化合物存在大量且不断增长的需求。对于用于聚合材料中的更安全的不饱和化合物的主要探索是针对关于目前使用的不饱和化合物(例如丙烯酸和烯丙基化合物)的合适替代物。
发明内容
现在非常出乎意料地发现2-羟基-3-丁烯酸及其酯与异氰酸酯反应产生了低聚物和聚合物，其可以适当地替换例如上文讨论的低聚物和聚合物。所述2-羟基-3-丁烯酸及其甲酯(甲基乙烯基乙醇酸酯)容易地经由例如乳酸从生物质中获得。
相应的，本发明的目的是提供一种新的不饱和低聚物或聚合物，其是化合物(例如改性和未改性的氨基甲酸酯丙烯酸酯和甲基丙烯酸酯)的合适补充和/或替代。本发明进一步的目的是提供从可再生资源(例如生物质)获得的合适的补充和/或替代。
相应的，本发明的实施方案包括通过使至少一种具有两个或更多个异氰酸酯基团的单体、低聚或聚合异氰酸酯与2-羟基-3-丁烯酸和/或2-羟基-3-丁烯酸的至少一种烷基酯反应而获得的低聚物或聚合物，因此产生氨基甲酸酯低聚物或聚合物。发现异氰酸酯基团/羟基基团的合适比率在，但不限于，例如0.8-1.2至1.2-0.8之间的比率内。
所述异氰酸酯可以是适当地通过但不限于以下例示的优选实施方案：亚甲基二异氰酸酯、六亚甲基二异氰酸酯、异佛尔酮二异氰酸酯、甲苯二异氰酸酯、亚甲基二苯基二异氰酸酯、五亚甲基二异氰酸酯和/或萘二异氰酸酯和/或具有两个或更多个异氰酸酯基团的亚甲基二异氰酸酯、六亚甲基二异氰酸酯、异佛尔酮二异氰酸酯、甲苯二异氰酸酯、亚甲基二苯基二异氰酸酯、五亚甲基二异氰酸酯和/或萘二异氰酸酯的至少一种低聚物或聚合物，例如二聚物或三聚物。进一步的异氰酸酯包括单体、低聚和聚合三异氰酸酯。
所述2-羟基-3-丁烯酸的烷基酯合适地且优选地为C1-C4-烷基酯，例如甲酯或乙酯，甲基乙烯基乙醇酸酯或乙基乙烯基乙醇酸酯。进一步的合适酯可以通过但不限于以下例示：2-羟基-3-丁烯酸的2-乙基-庚醇、2-丙基-庚醇、5-羟基-1,3-二噁烷、5-羟甲基-1,3-二噁烷和5-羟乙基-1,3-二噁烷酯。
所述2-羟基-3-丁烯酸和/或所述2-羟基-3-丁烯酸的至少一种烷基酯，当然可以在所述反应中与至少一种异氰酸酯、与一种或多种其它羟基官能化合物混合，所述羟基官能化合物例如单、二、三或多羟基官能醇，单、二、三或多羟基官能羧酸和/或单、二、三或多羟基官能丙烯酸酯、甲基丙烯酸酯或巴豆酸酯。这些化合物可以通过以下例示：丁二醇、丙二醇、庚二醇、戊二醇、己二醇、二丙二醇、三甘醇、环己烷二甲醇、2-丁基-2-乙基-1,3-丙二醇、新戊二醇、5,5-二羟基甲基-1,3-二噁烷、季戊四醇螺二醇、甘油、三羟甲基乙烷、三羟甲基丙烷、三羟甲基丁烷、季戊四醇、双三羟甲基乙烷、双三羟甲基丙烷、双三羟甲基丁烷、双季戊四醇、三季戊四醇，所述二醇、三醇或多元醇的烷氧基化的(例如乙氧基化、丙氧基化和/或丁氧基化的)种类，乳酸、乙醇酸、苹果酸、羟基丁酸、羟基丁烯酸(例如2-羟基-3-丁烯酸)、羟基己酸、马来酸、柠檬酸、酒石酸和/或水杨酸。
在本发明的某些优选实施方案中，所述低聚物或聚合物随后在第二步骤中与至少一种内酯二醇、三醇或多元醇反应。用于获得根据本发明的低聚物或聚合物的所述内酯二醇、三醇或多元醇优选地选自低聚和聚合的乙内酯、丙内酯、丁内酯、戊内酯和/或己内酯。尤其优选的实施方案是具有100-2000(例如200-1000)的分子量(Mn)，以及100-500(例如150-300)mg KOH/g的羟基值的己内酯二醇、三醇和多元醇。
在另一方面，本发明涉及包含上文公开的低聚物或聚合物的组合物。所述组合物的实施方案可以另外包含至少一种具有至少一个碳-碳双键的丙烯酸酯、甲基丙烯酸酯或巴豆酸酯，例如二醇的丙烯酸、甲基丙烯酸或巴豆酸单酯和二酯，三醇的单酯、二酯和三酯，四醇的单酯、二酯、三酯和四酯，五醇的单酯、二酯、三酯、四酯和五酯，六醇的单酯、二酯、三酯、四酯、五酯和六酯，具有七个或更多个羟基的超支化树枝状多元醇和羟基官能化合物的单酯、二酯、三酯、低聚酯或聚酯，和/或为至少一种具有至少一个碳-碳双键的烯丙基醚或甲基烯丙基醚，例如二醇的单醚和二醚，三醇的单醚、二醚和三醚，四醇的单醚、二醚、三醚和四醚，五醇的单醚、二醚、三醚、四醚和五醚，六醇的单醚、二醚、三醚、四醚、五醚和六醚，以及具有七个或更多个羟基的超支化树枝状多元醇和羟基官能化合物的二酯、三酯、低聚酯或聚酯的单醚、二醚、三醚、低聚醚或聚醚。
所述二醇、三醇或多元醇的实施方案包括但不限于丁二醇、丙二醇、庚二醇、戊二醇、己二醇、二丙二醇、三甘醇、环己烷二甲醇、2-丁基-2-乙基-1,3-丙二醇、新戊二醇、5,5-二羟基甲基-1,3-二噁烷、季戊四醇螺二醇、甘油、三羟甲基乙烷、三羟甲基丙烷、三羟甲基丁烷、苯二甲基三醇(苯三甲醇)、季戊四醇、双三羟甲基乙烷、双三羟甲基丙烷、双三羟甲基丁烷、双季戊四醇、三季戊四醇、脱水烯-庚糖醇(anhydroenea-heptitol)，己内酯二醇、三醇和多元醇，对于所述二醇、三醇和多元醇相对应的聚碳酸酯二醇、三醇或多元醇，以及所述二醇、三醇或多元醇的烷氧基化的(例如乙氧基化、丙氧基化和/或丁氧基化的)种类，具有例如1-20个烷氧基单元/分子的烷氧基程度。
在进一步的实施方案中，根据本发明的组合物可以适当地并且另外包含至少一种环氧(甲基)丙烯酸酯、胺改性的环氧(甲基)丙烯酸酯、氨基甲酸酯(甲基)丙烯酸酯、双酚A(甲基)丙烯酸酯、聚酯(甲基)丙烯酸酯、聚醚(甲基)丙烯酸酯、胺改性的聚醚(甲基)丙烯酸酯、酸官能(甲基)丙烯酸酯、月桂基(甲基)丙烯酸酯、壬基酚(甲基)丙烯酸酯、烷氧基化的(例如乙氧基化、丙氧基化和/或丁氧基化)壬基酚(甲基)丙烯酸酯、氧杂环丁烷(甲基)丙烯酸酯、氰基(甲基)丙烯酸酯和/或四氢糠基(甲基)丙烯酸酯。
在再进一步的实施方案中，所述组合物可以合适地并且另外包含至少一种乙烯基单体、低聚物或聚合物，例如但不限于乙烯基吡咯烷酮，聚烯烃(包括聚乙烯、聚丙烯和聚丁二烯)，苯乙烯(包括聚苯乙烯)，卤化乙烯(包括聚氯乙烯和聚氟乙烯)，乙酸乙烯酯(包括聚乙酸乙烯酯)，乙烯醇(包括聚乙烯醇)，和丙烯腈(包括聚丙烯腈)。
当然，所述组合物还可以另外包含至少一种消光剂、流动剂/流平剂、流变改性剂、染料和/或颜料。
在尤其优选的实施方案中，根据本发明的组合物是辐射(例如UV)可固化的组合物，其包含至少一种选自自由基、阳离子和阴离子光敏引发剂的光敏引发剂。所述光敏引发剂可以通过但不限于以下例示：锑酸锍(sulphonium antimonate，例如三芳基六锑酸锍、氟锑酸锍)、氟磷酸锍(例如三芳基六氟磷酸锍)、硝酸锍、三氟甲磺酸锍、氟磷酸碘鎓酯(例如二甲基-二苯基六氟磷酸碘鎓酯)、羟基(环)烷基芳基酮(例如羟基环己基苯基酮)、金属茂(例如二茂铁、二茂钌(rhutenocennes)和二茂钛)、酮洛芬、苯偶姻醚、苯偶酰缩酮、二苯甲酮、苯乙酮、氨基烷基苯甲酮(aminoalkylphenone)、酰基氧化膦、benzoephenone、噻吨酮(thixantone)、蒽醌和樟脑醌。
在又一方面，本发明涉及低聚物或聚合物以及如例如上文公开的组合物在以下中的用途：用于木材、金属、塑料、纺织品和纸张的涂层(包括触觉涂层)，柔版和数字油墨，3D打印，图形艺术，粘合剂，医疗和牙科应用和装置，吸收剂，卫生制品，包装，电子和电应用和装置，和/或光学应用和装置。
无需进一步阐述，相信本领域技术人员可以使用前面的描述来最大程度地利用本发明。因此，下述优选的具体实施方案应被解释为仅是示例性的，而绝不以任何形式是限制性的。在下述实施例1和2中显示了根据本发明的低聚物/聚合物的实施方案，实施例3和4是在本发明的范围之外的比较低聚物/聚合物，并且实施例5和6指根据本发明的实施方案的组合物，及其与基于实施例3和4的比较低聚物/聚合物的组合物的比较的评估。
具体实施方式
实施例1
将按重量计69份的分子量Mn为900的三官能六亚甲基二异氰酸酯缩二脲(TolonateTM HDB 75B，Vencorex Chemicals)、按重量计50份的甲苯、以及按重量计0.1份的作为抗氧化剂的4-甲氧基苯酚装入反应容器中，所述反应容器配备有加热、搅拌器、空气入口和冷却器，并且将按重量计60份的甲基乙烯基乙醇酸酯缓慢装入混合物中，随后加入按重量计0.01份的作为反应催化剂的辛酸亚锡。反应在80℃下执行10小时。在反应完成后，甲苯蒸发。
所得到的产物具有1800的分子量(Mn)和1.5的多分散度。
实施例2
步骤I：将按重量计58份的异佛尔酮二异氰酸酯、按重量计50份的甲苯、以及按重量计0.1份的作为抗氧化剂的4-甲氧基苯酚装入反应容器中，所述反应容器配备有加热、搅拌器、空气入口和冷却器，并且将按重量计28份的甲基乙烯基乙醇酸酯缓慢装入混合物中，随后加入按重量计0.01份的作为催化剂的辛酸亚锡。反应在80℃下执行6小时。
所得到的产物具有322的分子量(Mn)和8.6的NCO值。
步骤II：将按重量计40份的步骤I中得到的产物、按重量计19份的己内酯二醇(CAPATM 2043，Perstorp Specialty Chemicals)(具有400的分子量Mn和280mg KOH/g的羟值)、按重量计0.05份的4-甲氧基苯酚、以及按重量计0.01份的辛酸亚锡装入反应容器中，所述反应容器配备有加热、搅拌器、空气入口和冷却器，并且允许在80℃下反应12小时。
在反应完成后，甲苯蒸发。
所得到的产物具有1200的分子量(Mn)和2.0的多分散度。
实施例3(比较)
将按重量计69份的分子量Mn为900的三官能六亚甲基二异氰酸酯缩二脲(TolonateTM HDB 75B，Vencorex Chemicals)、按重量计50份的甲苯、以及按重量计0.1份的作为抗氧化剂的4-甲氧基苯酚装入反应容器中，所述反应容器配备有加热、搅拌器、空气入口和冷却器，并且将按重量计60份的丙烯酸羟乙酯缓慢装入混合物中，随后加入按重量计0.01份的作为反应催化剂的辛酸亚锡。反应在80℃下执行11小时。
在反应完成后，甲苯蒸发。
所得到的产物具有1815的分子量(Mn)和1.7的多分散度。
实施例4(比较)
步骤I：将按重量计58份的异佛尔酮二异氰酸酯、按重量计50份的甲苯、以及按重量计0.1份的作为抗氧化剂的4-甲氧基苯酚装入反应容器中，所述反应容器配备有加热、搅拌器、空气入口和冷却器，并且将按重量计28份的丙烯酸羟乙酯缓慢装入混合物中，随后加入按重量计0.01份的作为催化剂的辛酸亚锡。反应在80℃下执行7小时。
所得到的产物具有343的分子量(Mn)和8.3的NCO值。
步骤II：将按重量计40份的步骤I中得到的产物、按重量计15份的己内酯二醇(CAPATM 2043，Perstorp Specialty Chemicals)(具有400的分子量Mn和280mg KOH/g的羟值)、按重量计0.05份的4-甲氧基苯酚、以及按重量计0.01份的辛酸亚锡装入反应容器中，所述反应容器配备有加热、搅拌器、空气入口和冷却器，并且允许在80℃下反应12小时。
在反应完成后，甲苯蒸发。
所得到的产物具有1400的分子量(Mn)和1.6的多分散度。
实施例5
将实施例1-4中产生的产物与光敏引发剂(IrgacureTM 500)以重量比96：4(产物：光敏引发剂)混合，并且使用H-型灯泡进行UV固化，其中效果设为100％。根据ASTM D 4752-98，将获得的混合物涂布在玻璃面板上，并且膜厚度(未固化)对于硬度测量(
Figure BDA0002394599000000083
secs.)为40μm且对于MEK-rubs为12μm。
Figure BDA0002394599000000081
实施例6
将实施例1-4中产生的产物与二丙烯酸己二醇酯(HDDA)和光敏引发剂(IrgacureTM500)以重量比50：46：4(产物：HDDA：光敏引发剂)混合，并且使用H-型灯泡进行UV固化，其中效果设为100％。根据ASTM D 4752-98，将获得的混合物涂布在玻璃面板上，并且膜厚度(未固化)对于硬度测量(
Figure BDA0002394599000000084
secs.)为40μm且对于MEK-rubs为12μm。
Figure BDA0002394599000000082

Claims (25)

1.低聚物或聚合物，其特征在于，所述低聚物或聚合物通过使至少一种具有两个或更多个异氰酸酯基团的单体、低聚或聚合异氰酸酯与2-羟基-3-丁烯酸和/或2-羟基-3-丁烯酸的至少一种烷基酯反应而获得。
2.根据权利要求1的低聚物或聚合物，其特征在于，所述异氰酸酯是亚甲基二异氰酸酯、六亚甲基二异氰酸酯、异佛尔酮二异氰酸酯、甲苯二异氰酸酯、亚甲基二苯基二异氰酸酯、五亚甲基二异氰酸酯和/或萘二异氰酸酯。
3.根据权利要求1或2的低聚物或聚合物，其特征在于，所述异氰酸酯是亚甲基二异氰酸酯、六亚甲基二异氰酸酯、异佛尔酮二异氰酸酯、甲苯二异氰酸酯、亚甲基二苯基二异氰酸酯、五亚甲基二异氰酸酯和/或萘二异氰酸酯的至少一种低聚物或聚合物。
4.根据权利要求1-3中任一项的低聚物或聚合物，其特征在于，所述2-羟基-3-丁烯酸的烷基酯是C1-C4-烷基酯。
5.根据权利要求1-4中任一项的低聚物或聚合物，其特征在于，所述2-羟基-3-丁烯酸的烷基酯是甲酯或乙酯。
6.根据权利要求5的低聚物或聚合物，其特征在于，所述甲酯或乙酯是甲基乙烯基乙醇酸酯或乙基乙烯基乙醇酸酯。
7.根据权利要求1-3中任一项的低聚物或聚合物，其特征在于，所述2-羟基-3-丁烯酸的酯是与2-乙基-庚醇、2-丙基-庚醇、5-羟基-1,3-二噁烷、5-羟甲基-1,3-二噁烷或5-羟乙基-1,3-二噁烷形成的酯。
8.根据权利要求1-7中任一项的低聚物或聚合物，其特征在于，使在所述反应之后所得到的低聚物或聚合物与至少一种内酯二醇、三醇或多元醇反应。
9.根据权利要求8的低聚物或聚合物，其特征在于，所述内酯二醇、三醇或多元醇选自低聚和/或聚合的乙内酯、丙内酯、丁内酯、戊内酯和/或己内酯。
10.根据权利要求8或9的低聚物或聚合物，其特征在于，所述内酯二醇、三醇或多元醇是具有100-2000的分子量Mn以及100-500mg KOH/g的羟基值的己内酯二醇、三醇或多元醇。
11.组合物，其包含至少一种根据权利要求1-10中任一项的低聚物或聚合物。
12.根据权利要求11的组合物，其特征在于，它另外包含二醇、三醇或多元醇的至少一种丙烯酸酯、甲基丙烯酸酯或巴豆酸酯。
13.根据权利要求12的组合物，其特征在于，所述丙烯酸酯、甲基丙烯酸酯或巴豆酸酯是二醇的单酯或二酯，三醇的单酯、二酯或三酯，四醇的单酯、二酯、三酯或四酯，五醇的单酯、二酯、三酯、四酯或五酯，或者六醇的单酯、二酯、三酯、四酯、五酯或六酯。
14.根据权利要求11-13中任一项的组合物，其特征在于，它另外包含二醇、三醇或多元醇的至少一种烯丙基醚。
15.根据权利要求14的组合物，其特征在于，所述烯丙基或甲基烯丙基醚是二醇的单醚或二醚，三醇的单醚、二醚或三醚，四醇的单醚、二醚、三醚或四醚，五醇的单醚、二醚、三醚、四醚或五醚，或者六醇的单醚、二醚、三醚、四醚、五醚或六醚。
16.根据权利要求12-15中任一项的组合物，其特征在于，所述二醇是丁二醇、丙二醇、庚二醇、戊二醇、己二醇、二丙二醇、三甘醇、环己烷二甲醇、2-丁基-2-乙基-1,3-丙二醇、新戊二醇、5,5-二羟基甲基-1,3-二噁烷或季戊四醇螺二醇。
17.根据权利要求12-15中任一项的组合物，其特征在于，所述二醇是烷氧基化的，例如乙氧基化、丙氧基化和/或丁氧基化的新戊二醇、5,5-二羟基甲基-1,3-二噁烷或季戊四醇螺二醇。
18.根据权利要求12-15中任一项的组合物，其特征在于，所述三醇是甘油、三羟甲基乙烷、三羟甲基丙烷或三羟甲基丁烷。
19.根据权利要求12-15中任一项的组合物，其特征在于，所述三醇是烷氧基化的，例如乙氧基化、丙氧基化和/或丁氧基化的甘油、三羟甲基乙烷、三羟甲基丙烷或三羟甲基丁烷。
20.根据权利要求12-15中任一项的组合物，其特征在于，所述多元醇是季戊四醇、双三羟甲基乙烷、双三羟甲基丙烷、双三羟甲基丁烷和/或双季戊四醇。
21.根据权利要求12-15中任一项的组合物，其特征在于，所述多元醇是烷氧基化的，例如乙氧基化、丙氧基化和/或丁氧基化的季戊四醇、双三羟甲基乙烷、双三羟甲基丙烷、双三羟甲基丁烷和/或双季戊四醇。
22.根据权利要求11-21中任一项的组合物，其特征在于，所述组合物是辐射固化组合物。
23.根据权利要求11-22中任一项的组合物，其特征在于，所述组合物是UV固化组合物,该UV固化组合物包含至少一种光敏引发剂，例如自由基、阳离子和/或阴离子光敏引发剂。
24.根据权利要求1-10中任一项的低聚物或聚合物在木材涂层、金属涂层、塑料涂层、纺织品涂层、纸张涂层、柔版和数字油墨、3D打印、图形艺术、粘合剂、医疗和牙科应用和装置、吸收剂、卫生制品、包装、电子和电应用和装置、和/或光学应用和装置中的用途。
25.根据权利要求11-23中任一项的组合物在木材涂层、金属涂层、塑料涂层、纺织品涂层、纸张涂层、柔版和数字油墨、3D打印、图形艺术、粘合剂、医疗和牙科应用和装置、吸收剂、卫生制品、包装、电子和电应用和装置、和/或光学应用和装置中的用途。
CN201880056107.4A 2017-08-31 2018-08-30 新型低聚物或聚合物以及包含其的组合物 Pending CN111051378A (zh)

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