CN108602923B - 辐射固化组合物 - Google Patents
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Abstract
公开了一种辐射可固化组合物,包含2‑羟基‑3‑丁烯酸和/或至少一种2‑羟基‑3‑丁烯酸的酯和至少一种选自辐射可固化单体、低聚物和聚合物的另外的化合物。
Description
本发明涉及一种新的辐射可固化组合物,包含2-羟基-3-丁烯酸和/ 或至少一种2-羟基-3-丁烯酸的酯和至少一种选自辐射可固化单体、低 聚物和聚合物的另外的化合物。
具有一个或多个碳-碳双键(不饱和现象)的化学化合物是本领域熟 知的,在各种各样的应用以及在例如模塑和浇铸组合物等中用作反应物 和化学构建块(chemicalbuilding blocks),所述应用比如干燥和/或热 固化和/或UV、IR和EB固化漆、瓷釉、腻子、油漆、清漆、粘合剂和油 墨、酯和聚酯、胶乳、纤维、织物等。然而,尽管存在大量市售可获得的不饱和化合物及其衍生物,但是由于例如环境问题和环境法规和/或新 的应用领域,对于新的、更安全的、更有效的和/或更通用的具有一个或 多个碳-碳双键的化合物存在大量日益增长的需求。对于聚合物材料中使 用的更安全的不饱和化合物的主要寻找目标(major search)针对目前使 用的不饱和化合物比如丙烯酸化合物和烯丙基化合物的合适替代物。
本发明的一个目的是提供一种新的具有至少一个碳-碳双键的不饱 和化合物。一个进一步的目的是提供一种化合物比如丙烯酸酯、甲基丙 烯酸酯和巴豆酸酯(crotonicester)、烯丙基醚和甲基烯丙基醚、及包 含至少一种乙烯基不饱和现象的其它化合物的合适的补充物和/或替代 物。仍然一个进一步的目的是提供从可再生来源比如生物质(biomass) 获得的所述合适的补充物和/或替代物。
现在,相当出人意料地发现2-羟基-3-丁烯酸及其酯提供优良的辐 射固化组合物,其中所述酸和/或所述酯用作具有例如一个或多个碳-碳 双键的辐射可固化化合物(比如丙烯酸酯、甲基丙烯酸酯和巴豆酸酯、烯 丙基醚或甲基烯丙基醚、和/或化合物比如乙烯基单体、低聚物和聚合物) 的补充物或替代物。2-羟基-3-丁烯酸及其甲酯、甲基乙烯基乙醇酸酯是 经由例如乳酸从生物质容易获得的。所述2-羟基-3-丁烯酸和所述甲基 乙烯基乙醇酸酯可以经由与一元醇、二元醇、三元醇和多元醇的酯化或 酯交换容易地转化成大量具有一个或多个乙烯基不饱和现象的通用化合 物。
因此,本发明的实施方案包括其中所包括的组分中至少一种为2- 羟基-3-丁烯酸或2-羟基-3-丁烯酸的酯的组合物。在多个实施方案中, 所述酯为直链或支链烷基酯,比如甲基或乙基乙烯基乙醇酸酯、或2-羟 基-3-丁烯酸和一元醇的酯,所述一元醇为比如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。进一步的实施方案包括2-羟基-3-丁烯酸和二、三或多羟基官能化 合物比如二醇、三醇、四醇、五醇、六醇和超支化树枝状多元醇的酯。 因此,这些实施方案包括酯类,比如二醇的单酯和二酯,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,以及 具有七个或更多个羟基的羟基官能化合物的单酯、低聚酯或聚酯。
在本发明的实施方案中,所述另外的化合物为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,比如丙烯酸、甲基 丙烯酸或巴豆酸的二醇的单酯和二酯,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、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(低聚)酯或聚酯, 和/或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,比 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、六醚和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(低聚)酯或聚酯的单醚、二醚或聚醚。
所述二醇的实施方案包括,但不限于式HO-R-OH的化合物,其中R 为直链或支链烷基、环烷基或芳基基团,并且可以合适地举例为丁二醇、 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-乙基-2-丁基-1,3-丙二醇、新戊二醇、5,5-二羟基甲基-1,3-二噁烷、 苯二甲基二醇(苯二甲醇)、季戊四醇螺环二醇(pentaerythitolspiroglycol)和己内酯二醇和/或所述二醇对应的聚碳酸酯二醇。所述二 醇的进一步合适的实施方案包括烷氧基化的比如乙氧基化的、丙氧基化 的和/或丁氧基化的、具有例如1-20个烷氧基单位/分子的烷氧基化度 (alkoxylation degree)的、新戊二醇、5,5-二羟基甲基-1,3-二噁烷、 苯二甲基二醇(苯二甲醇)和季戊四醇螺环二醇。所述二醇的仍然进一步合适的实施方案包括化合物比如双酚A和双酚F以及烷氧基化的比如乙 氧基化的、丙氧基化的和/或丁氧基化的、具有如之前所述烷氧基化度的 其种类。
所述三醇的实施方案可以举例为,但不限于丙三醇、三羟甲基乙烷、 三羟甲基丙烷、三羟甲基丁烷、三苄醇(xylylene triol)(苯三甲醇)、 己内酯三醇、所述三醇对应的聚碳酸酯三醇以及烷氧基化的比如乙氧基 化的、丙氧基化的和/或丁氧基化的、具有例如1-20个烷氧基单位/分子 的烷氧基化度的、丙三醇、三羟甲基乙烷、三羟甲基丙烷、三羟甲基丁 烷或三苄醇(苯三甲醇)。
所述四醇的实施方案可以举例为,但不限于季戊四醇、二-三羟甲 基乙烷、二-三羟甲基丙烷、二-三羟甲基丁烷、己内酯四醇、所述四醇 对应的聚碳酸酯四醇以及烷氧基化的比如乙氧基化的、丙氧基化的和/ 或丁氧基化的、具有例如1-20个烷氧基单位/分子的烷氧基化度的、季 戊四醇、二-三羟甲基乙烷、二-三羟甲基丙烷和二-三羟甲基丁烷。所述 五醇的实施方案可以举例为,但不限于脱水壬七醇 (anhydroenneaheptitol)、木糖醇、己内酯五醇、所述五醇对应的聚碳 酸酯五醇以及烷氧基化的比如乙氧基化的、丙氧基化的和/或丁氧基化 的、具有例如1-20个烷氧基单位/分子的烷氧基化度的、脱水壬七醇或 木糖醇。
所述六醇的实施方案可以举例为,但不限于二-季戊四醇、山梨醇、 甘露醇、己内酯六醇、所述六醇对应的聚碳酸酯六醇以及烷氧基化的比 如乙氧基化的、丙氧基化的和/或丁氧基化的、具有例如1-20个烷氧基 单位/分子的烷氧基化度的、二-季戊四醇、山梨醇或甘露醇。
在本发明的实施方案中,所述组合物合适地另外包括至少一种环氧 (甲基)丙烯酸酯、胺改性的环氧(甲基)丙烯酸酯、氨基甲酸乙酯(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、酸官能的(甲基)丙烯酸酯、 月桂基(甲基)丙烯酸酯、壬基酚(甲基)丙烯酸酯、烷氧基化的比如乙氧基化的、丙氧基化的和/或丁氧基化的、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。
在本发明的进一步实施方案中,所述组合物可以合适地另外包括至 少一种乙烯基单体、低聚物或聚合物,比如乙烯基吡硌烷酮、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、乙烯基卤化物包 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。
在本发明的仍然进一步的实施方案中,所述组合物为UV、IR和EB 可固化组合物,并且可以任选地另外包括至少一种消光剂、助流剂/流平 剂、流变学改性剂、染料和/或颜料。
在特别优选的实施方案中,本发明的组合物为UV可固化组合物, 其另外包括至少一种光引发剂比如至少一种自由基、阳离子和/或阴离子 光引发剂。合适的光引发剂可以举例但不限于锑酸硫鎓(sulphonium antimonates),比如六锑酸三芳基硫鎓,氟代锑酸硫鎓比如六氟代磷酸 三芳基硫鎓,硝酸硫鎓,三氟甲磺酸硫鎓,氟代磷酸碘鎓,氟代磷酸硫鎓比如六氟代磷酸二甲基-二苯基碘鎓,羟基(环)烷基芳基酮比如羟基环 己基苯基酮(droxycyclohexylphenyl ketones),茂金属比如二茂铁、 rhutenocennes和二茂钛(titanocenes)、酮洛芬、苯偶姻醚、苯偶酰缩 酮(benzil ketals)、二苯甲酮、苯乙酮、氨基烷基苯甲酮、酰基氧化膦、 二苯甲酮(benzoephenones)、硫杂蒽酮(thixantones)、蒽醌和/或樟 脑醌。
在一个进一步的方面,本发明涉及如上述公开的组合物在用于木 材、金属、塑料、织物和纸、柔性和数字油墨、3D打印、版画艺术、粘 合剂、医学和牙齿应用和装置、吸收物、卫生制品、包装、电子和导电 应用和装置、和/或光学应用和装置的涂层包括触感涂层中的用途。在仍 然一个进一步的方面,本发明涉及2-羟基-3-丁烯酸或甲基或乙基乙烯 基乙醇酸酯作为反应性稀释剂在辐射可固化组合物中的用途。
无需进一步详述,据信本领域技术人员可以使用前述说明书以其最 大程度地利用本发明。因此,下述优选的特定实施方案应当被看作仅仅 是示例性的,而无论如何不是以任何方式限制性的。在下述实施例中, 显示出2-羟基-3-丁烯酸酯甲基乙烯基乙醇酸酯出人意料地是UV固化 的,尽管其仅具有一个碳-碳双键,实施例2显示所述酯与第二UV可固化化合物的组合得到优良的固化和优良的成膜性质。
实施例1
将96重量份的甲基乙烯基乙醇酸酯与4重量份的光引发剂500(CibaSpecialty Chemicals)混合,并且UV固化30*5 m/min,H-bulb设定为100%,在玻璃板上的膜厚度为40μm。
获得下述硬度(harness)性质:
使用的装置给予UV剂量J/cm2H-bulb设定为100%:
实施例2
将50重量份的甲基乙烯基乙醇酸酯与46重量份的二丙烯酸己二醇 酯和4重量份的光引发剂500(Ciba Specialty Chemicals) 混合,并且UV固化20*5m/min,H-bulb设定为100%,在玻璃板上的 膜厚度为40μm。
获得下述硬度性质:
使用的装置给予UV剂量J/cm2H-bulb设定为100%:
Claims (35)
1.2-羟基-3-丁烯酸和/或至少一种2-羟基-3-丁烯酸的酯作为反应性稀释剂在辐射可固化组合物中的用途,所述组合物包含至少一种选自辐射可固化单体和聚合物的另外的化合物。
2.根据权利要求1的用途,特征在于所述2-羟基-3-丁烯酸的酯为甲酯或乙酯。
3.根据权利要求2的用途,特征在于所述甲酯或乙酯为甲基乙烯基乙醇酸酯或乙基乙烯基乙醇酸酯。
4.根据权利要求1的用途,特征在于所述2-羟基-3-丁烯酸的酯为与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-1,3-二噁烷的酯。
5.根据权利要求1的用途,特征在于所述2-羟基-3-丁烯酸的酯为与超支化树枝状多元醇的酯。
6.根据权利要求1的用途,特征在于所述2-羟基-3-丁烯酸的酯为二醇的单酯或二酯,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,或六醇的单酯、二酯、三酯、四酯、五酯或六酯。
7.根据权利要求1的用途,特征在于所述另外的化合物为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。
8.根据权利要求7的用途,特征在于所述丙烯酸酯、甲基丙烯酸酯或巴豆酸酯为与超支化树枝状多元醇的酯。
9.根据权利要求7的用途,特征在于所述丙烯酸酯、甲基丙烯酸酯或巴豆酸酯为二醇的单酯或二酯,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,或六醇的单酯、二酯、三酯、四酯、五酯或六酯。
10.根据权利要求1的用途,特征在于所述另外的化合物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。
11.根据权利要求10的用途,特征在于所述烯丙基醚或甲基烯丙基醚为与超支化树枝状多元醇的醚。
12.根据权利要求10的用途,特征在于所述烯丙基醚或甲基烯丙基醚为二醇的单醚或二醚,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,或六醇的单醚、二醚、三醚、四醚、五醚或六醚。
13.根据权利要求9或12的用途,特征在于所述二醇为式HO-R-OH的化合物,其中R为直链或支链烷基、环烷基或芳基基团。
14.根据权利要求9或12的用途,特征在于所述二醇为丁二醇、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-乙基-2-丁基-1,3-丙二醇、新戊二醇、5,5-二羟基甲基-1,3-二噁烷、苯二甲基二醇、季戊四醇螺环二醇、己内酯二醇或所述二醇对应的聚碳酸酯二醇。
15.根据权利要求9或12的用途,特征在于所述二醇为烷氧基化的新戊二醇、5,5-二羟基甲基-1,3-二噁烷、苯二甲基二醇或季戊四醇螺环二醇。
16.根据权利要求9或12的用途,特征在于所述二醇为双酚A或双酚F。
17.根据权利要求9或12的用途,特征在于所述二醇为烷氧基化的双酚A或双酚F。
18.根据权利要求9或12的用途,特征在于所述三醇为丙三醇、三羟甲基乙烷、三羟甲基丙烷、三羟甲基丁烷、三苄醇、己内酯三醇或所述三醇对应的聚碳酸酯三醇。
19.根据权利要求9或12的用途,特征在于所述三醇为烷氧基化的丙三醇、三羟甲基乙烷、三羟甲基丙烷、三羟甲基丁烷或三苄醇。
20.根据权利要求9或12的用途,特征在于所述四醇为季戊四醇、二-三羟甲基乙烷、二-三羟甲基丙烷、二-三羟甲基丁烷、己内酯四醇或所述四醇对应的聚碳酸酯四醇。
21.根据权利要求9或12的用途,特征在于所述四醇为烷氧基化的季戊四醇、二-三羟甲基乙烷、二-三羟甲基丙烷或二-三羟甲基丁烷。
22.根据权利要求9或12的用途,特征在于所述五醇为脱水壬七醇、木糖醇、己内酯五醇或所述五醇对应的聚碳酸酯五醇。
23.根据权利要求9或12的用途,特征在于所述五醇为烷氧基化的脱水壬七醇或木糖醇。
24.根据权利要求9或12的用途,特征在于所述六醇为二-季戊四醇、山梨醇、甘露醇、己内酯六醇或所述六醇对应的聚碳酸酯六醇。
25.根据权利要求9或12的用途,特征在于所述六醇为烷氧基化的二-季戊四醇、山梨醇或甘露醇。
26.根据权利要求1的用途,特征在于所述组合物另外包括至少一种环氧(甲基)丙烯酸酯、胺改性的环氧(甲基)丙烯酸酯、氨基甲酸乙酯(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)丙烯酸酯或酸官能的(甲基)丙烯酸酯。
27.根据权利要求1的用途,特征在于所述组合物另外包括月桂基(甲基)丙烯酸酯、壬基酚(甲基)丙烯酸酯、烷氧基化的壬基酚(甲基)丙烯酸酯、氧杂环丁烷(甲基)丙烯酸酯、氰基(甲基)丙烯酸酯或四氢糠基(甲基)丙烯酸酯。
28.根据权利要求1的用途,特征在于所述组合物另外包括至少一种乙烯基单体或聚合物,选自乙烯基吡硌烷酮、聚烯烃、苯乙烯、乙烯基卤化物、乙酸乙烯酯、乙烯醇和丙烯腈。
29.根据权利要求1的用途,特征在于所述组合物另外包括至少一种消光剂、流平剂、流变学改性剂、染料或颜料。
30.根据权利要求1的用途,特征在于所述组合物是UV、IR和EB可固化组合物。
31.根据权利要求1的用途,特征在于所述组合物是UV可固化组合物,其另外包括至少一种光引发剂。
32.根据权利要求31的用途,特征在于所述光引发剂为自由基、阳离子或阴离子光引发剂。
33.根据权利要求31或32的用途,特征在于所述光引发剂为锑酸硫鎓、氟代锑酸硫鎓、氟代磷酸硫鎓、硝酸硫鎓、三氟甲磺酸硫鎓、氟代磷酸碘鎓、羟基烷基芳基酮、羟基环烷基芳基酮、茂金属、酮洛芬、苯偶姻醚、苯偶酰缩酮、苯乙酮、二苯甲酮、氨基烷基苯甲酮、氨基环烷基苯甲酮、酰基氧化膦、硫杂蒽酮、蒽醌或樟脑醌。
34.根据权利要求1的用途,其中所述组合物用在木材涂层、金属涂层、塑料涂层、织物涂层、纸涂层、柔性和数字油墨、3D打印、版画艺术、粘合剂、吸收物、卫生制品、包装、电子和导电应用和装置、或光学应用和装置中。
35.2-羟基-3-丁烯酸和/或至少一种2-羟基-3-丁烯酸的酯作为反应性稀释剂在制备辐射可固化组合物中的用途,所述组合物包含至少一种选自辐射可固化单体和聚合物的另外的化合物,所述辐射可固化组合物用于医学和牙齿应用和装置。
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SE1730230A1 (en) * | 2017-08-31 | 2019-02-19 | Perstorp Ab | Novel oligomer or polymer and composition comprising the same |
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