CN1163518C - 含马来酰亚胺衍生物的水相容性能量可固化组合物 - Google Patents
含马来酰亚胺衍生物的水相容性能量可固化组合物 Download PDFInfo
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- CN1163518C CN1163518C CNB988139316A CN98813931A CN1163518C CN 1163518 C CN1163518 C CN 1163518C CN B988139316 A CNB988139316 A CN B988139316A CN 98813931 A CN98813931 A CN 98813931A CN 1163518 C CN1163518 C CN 1163518C
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- Prior art keywords
- methyl
- acid
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- acrylate
- ester
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- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
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Abstract
本发明公开了能够以实际可行的强度和能量值固化的由马来酰亚胺衍生物、水相容性树脂和水组成的活性水相容性能量可固化组合物以及固化该组合物的方法。
Description
本发明的技术领域
本发明涉及含有马来酰亚胺衍生物的活性、水相容性、能量可固化的组合物,它可用于制备各种涂料、油墨、表面抛光剂、模塑制品、层压板、粘合剂和粘结剂。更准确地说,本发明涉及在没有光引发剂存在下利用具有实际可用强度和能量值的辐射源可以固化的一种活性、水相容性、能量可固化的组合物。
背景技术
在活化能如热能、紫外线、可见光等的辐射下聚合的一种活性、能量可固化组的合物具有快速固化的优点。活性能量可固化组合物广泛地被用作油漆、油墨、粘合剂、涂料等等。然而,普通的紫外线活性能量可固化组合物不能单独用能量源辐射引发聚合反应;所以有必要使用光引发剂。当光引发剂大量使用时,固化快速地进行,因此鼓励人们使用大量的光引发剂。
一般使用具有芳族环的光引发剂化合物,因为它们有效吸收紫外线。然而,这些化合物引起诸如在加热或光照之后固化材料泛黄的问题。而且,令人遗憾的是,由于溶解性—为有效地引发光聚合所需要的一种性能—而通常用作光引发剂的低分子量能量可固化单体和低聚物具有高蒸气压。因此,它们倾向于在从室温到150℃范围内的温度散发出令人不愉快的气味。因为例如从紫外线能量源产生红外光,活性能量可固化组合物在与该光源接触时已充分受热。当紫外光灯被排列并以并排方式使用时,生热问题更加突出。从光引发剂中散发出的令人不愉快的气味使得工作环境不太健康。
甚至在暴露于活性能量固化源的辐射之后,未反应的或分解的光引发剂仍残留在通常的能量可固化组合物中。这些未反应的或分解的光引发剂将导致诸如在固化膜暴露于热或光时该固化膜改变颜色为黄色、散发出难闻的气味等等问题。例如,当处在高温如加热头处的材料接触包含光引发剂的活性能量可固化组合物时,该材料将散发出强刺激性气味。最后,当这些固化的组合物在辐射之后接触水时,未反应的光引发剂将渗出;因此导致活性能量可固化组合物不适合用于食品包装应用。
为解决这些问题,现有技术中有多种选择。例如,JP-A-58-89609公开了包含具有可聚合不饱和丙烯酸基团的聚合物和有机溶剂可溶的含苯乙烯的丙烯酸热塑性树脂的一种不需要光引发剂的能量可固化树脂。
WO89/05827讲述了包括甲基丙烯酸酯单体和/或丙烯酸甲酯的共聚物和可光聚合的单体的一种可光聚合的粘合剂组合物。然而,这些可光致固化的组合物不能通过实际的辐射能量源充分地交联。
美国专利5,446,073和聚合物预印集,37卷,No.2,pp.348-49,1996,公开了光聚合方法,其中将马来酰亚胺型材料与乙烯基醚和丙烯酸酯混合来生产韧性薄膜。聚合机理涉及到由电子受体和电子给体形成的电荷转移配合物。然而,许多马来酰亚胺是固体并很难溶于丙烯酸酯中。
聚合物通讯(Polymer Letters),第6卷,pp883-88,1968,报道说马来酰亚胺衍生物可以在没有光引发剂存在下通过紫外光照射来聚合。日本专利申请JP-A-61-250064,JP-A-62-64813,和JP-A-62-79243描述了包含马来酰亚胺衍生物如烷基马来酰亚胺和芳基马来酰亚胺的活性能量可固化组合物。然而,这些马来酰亚胺衍生物显示出低的光引发剂性能,因此有必要在马来酰亚胺组合物中使用大量的光引发剂。
美国专利3,920,618和日本专利申请JP-A-50-123138和JP-A-51-47940公开了在侧链上有α-芳基取代的马来酰亚胺基团的可光聚合的聚合物。众所周知的是这些侧挂类型的马来酰亚胺能够通过紫外线照射法交联(即2+2光致环加成反应)。美国专利4,079,041和欧洲专利21019描述了具有带烷基取代基的侧链型马来酰亚胺基团的聚合物。然而,这些侧挂类型的马来酰亚胺不能用于由光致聚合作用形成线型聚合物。因此,他们最常常用于制备负片印刷板。另外,甚至以过量的照射能量,光致交联二聚反应发生相当长的时间(几十秒到几分钟)。
聚合物材料科学和工程(Polymer Materials Science andEngineering),72卷,pp.470-72,1995和Proceedings of RadTech Europe95,pp.34-56,1995公开了包括马来酰亚胺衍生物作为电子受体和乙烯基醚作为电子给体的可光致固化的组合物。在这些文件中叙述的可光致聚合的组合物1,4-双(乙烯基氧基甲基)环己烷和N-环己基马来酰亚胺或4-羟丁基乙烯基醚和N-(羟烷基)马来酰亚胺可在没有光引发剂存在下通过紫外辐射来聚合。然而,涂敷膜的硬化不会发生;即涂敷膜在紫外线照射后保持液态。
WO 98/07759描述了能量可固化组合物,其中水溶性马来酰亚胺与丙烯酸酯在没有水存在下共聚合而得到固化膜。
以上所述的聚合方法有许多问题,可以总结为:需要高辐射强度来充分地固化;马来酰亚胺衍生物在环境温度下为固体,这无法预示它们在没有光引发剂存在下是否可通过辐射来发生均聚;很难获得具有实际可用性能的固化涂层和得到所公开的宽范围的可固化组合物;需要比交联实际所需更多的辐射能量(光致二聚)。然而,这些参考文献没有描述含有水的活性能量可固化组合物或可与水相容的能量可固化组合物。
发明内容
本发明的目的是提供活性、水相容性、能量可固化组合物,它不含光引发剂,在固化后不发出难闻气味或不引起泛黄,或者在与水或溶剂接触后不从固化膜中渗出物质。
本发明的另一个目的是提供一种活性、水相容性、能量可固化组合物,它能够通过具有实际可行的强度和能量值的能量源进行光聚合并得到一种涂层,后者显示出与使用光引发剂的传统能量固化体系相当的固化速率、光泽、硬度和耐溶剂性能。
本发明涉及包括水相容性非乳化的非分散性的化合物、水和由结构式(1)表示的马来酰亚胺衍生物的一种活性、水可固化、能量可固化的单相组合物
其中n和m各自独立地表1至5中的整数,并且m和n的总数是6或更小;
R11和R12各自独立地表示选自直链或支链亚烷基、脂环族基团、芳基亚烷基和环烷基亚烷基的连接基团。所述芳基亚烷基和环烷基亚烷基可以分别具有芳基或环烷基作为主链或支链;
G1和G2各自独立地表示由-COO-或-OCO-表示的酯连接基;和
R2表示平均分子量为100至100,000的选自(聚)醚和(聚)酯连接链的一种连接链,其中至少一个基团是由选自直链或支链亚烷基、具有羟基的亚烷基、脂环族基团、芳基和芳基亚烷基的基团组成;而且通过选自醚和酯连接基的至少一个连接基相连。
本发明还提供一种包括上述活性、水相容性、能量可固化的单相组合物的油墨或涂料。
本发明进一步包括上述活性、水相容性、能量可固化的单相组合物固化的方法,它包括对所述的组合物进行辐射。
具体实施方式
本发明的活性、水可固化、能量可固化的组合物含有以上结构式1所示的马来酰亚胺衍生物。对于结构式1中的变量R11和R12,适合用于本发明中的R11和R12的例子包括直链亚烷基如亚甲基、亚乙基、三亚甲基、四亚甲基、五亚甲基、六亚甲基、七亚甲基、八亚甲基、九亚甲基、十亚甲基、十一亚甲基、十二亚甲基等;具有支链烷基的亚烷基如1-甲基亚乙基,1-甲基-三亚甲基,2-甲基-三亚甲基,1-甲基-四亚甲基,2-甲基-四亚甲基,1-甲基-五亚甲基,2-甲基-五亚甲基,3-甲基-五亚甲基,新戊基等;脂环族基团如亚环戊基,亚环己基等;在主链或侧链上有芳基的芳基亚烷基,如亚苄基,2,2-二苯基-三亚甲基,1-苯基-亚乙基,1-苯基-四亚乙基,2-苯基-四亚乙基等;在主链或侧链上有脂环族基团的环烷基亚烷基,如环己基-亚甲基,1-环己基-亚乙基,1-环己基-四亚乙基,2-环己基-四亚乙基等等。然而,对这些基团没有特别的限制。
当作为(聚)醚或(聚)酯连接链的R2的平均分子量低于100时,其马来酰亚胺的固化性能变差。即使该组合物发生固化,该能量固化的组合物的[凝胶分数]倾向于较低。
凝胶分数是固化膜在例如丁酮中于80℃下回流3小时、然后在100℃下干燥1小时后所剩下的物质的百分数。凝胶分数为99.8%的固化的马来酰亚胺衍生物或组合物表明了仅仅0.2%的基质被以上回流条件所溶解(即,高转化率)。
百分转化率被定义为在辐射过程中通过IR吸收谱带的消失所监控到的官能团与交联基质之比率。该即时IR测量使得人们能够定量测定转化率并提供了考察辐射过程中组合物的反应活性的手段。
附图的简述
图1和2显示了由即时红外分析所测量的马来酰亚胺至聚合马来酰亚胺材料的百分转化率随时间变化的曲线图。
如上所述,随着R2的分子量的减少,马来酰亚胺的固化性能变坏。图1显示了对于其中R2是聚四亚甲基二醇的双马来酰亚胺衍生物(所示结构)的即时IR数据的曲线图。随着重复单元(n)的分子量减少(即,4000(曲线1);3000(曲线2),1000(曲线3);650(曲线4);和250(曲线5))其转化速率变低。然而,当R2的分子量(曲线6)低于100时,即时IR数据揭示了转化速率变得迟缓。这支持使用其中R2(即,聚(醚)、聚(酯)连接链)大于100的马来酰亚胺衍生物,因为较低的值导致较差的转化速率。
图2显示了对于其中R2是聚乙二醇的双马来酰亚胺衍生物(所示结构)的即时IR数据的曲线图。随着重复单元(n)的分子量减少(即1000(曲线1);600(曲线2);400(曲线3);300(曲线4))该转化速率变低。然而,当R2的分子量(曲线5和6)低于100时,即时IR数据揭示了转化速率变得迟缓。
所以,图1和2的结果提示R2的平均分子量应高于100。另一方面,当R2的平均分子量高于100,000时,如对于多元醇或聚酯而言,则连接链的原料属于固体性质并且在环境温度下在普通溶剂中显示出差的溶解度。一旦获得,这些马来酰亚胺衍生物事实上不溶于普通的溶剂,所以,使得很难获得膜和固化它。即使获得了固化的涂膜,涂层表面显示出不平整。所以,R2的平均分子量高于100,000是不合适的。R2也可以是包括含有上述(聚)醚和(聚)酯基团作为重复单元的低聚物或聚合物的连接基。适合用于本发明中的R2的例子包括平均分子量在100-100,000范围内的(聚)醚或(聚)酯连接链。
由R2表示的连接链包括:(聚)醚(多)醇残基;(聚)酯(多)醇残基;在端部具有多羧酸残基的(多)羧酸{(聚)醚(多)醇}酯;在端部具有多羧酸残基的(多)羧酸{(聚)酯(多)醇}酯;和形成连接链的(聚)环氧化物。
由(聚)醚(多)醇残基表示的连接链具有平均分子量100至100,000,并且包括其中选自直链或支链C2-C24亚烷基、C3-C24脂环族基和C6-C24芳基的至少一个基团与醚连接链相连的部分或其重复单元。构成连接链的(聚)醚(多)醇的例子包括聚亚烷基二醇如聚乙二醇,聚丙二醇,聚丁二醇,聚四亚甲基二醇等;改性的亚烷基二醇,其中乙二醇,丙烷二醇,亚丙基二醇,丁二醇,五亚甲基二醇,己二醇,新戊基二醇,甘油,三羟甲基丙烷,季戊四醇,二甘油,双三羟甲基丙烷,双季戊四醇等被环氧乙烷、环氧丙烷、环氧丁烷和四氢呋喃改性。在这些(聚)醚(多)醇中,改性亚烷基二醇是优选的。还有,构成上述连接链的(聚)醚(多)醇的例子包括烃多元醇如环氧乙烷和环氧丙烷的共聚物,丙二醇和四氢呋喃的共聚物,乙二醇和四氢呋喃的共聚物,聚异戊二烯二醇,氢化的聚异戊二烯二醇,聚丁二烯二醇,氢化的聚丁二烯二醇等;多元醇化合物如聚四亚甲基六甘油醚(被四氢呋喃改性的六甘油),等等。然而,对这些(聚)醚(多)醇没有特殊限制。
由(聚)酯(多)醇残基表示的连接链具有平均分子量100至100,000,并且包括其中选自直链或支链C2-C24亚烷基、C3-C24脂环族基和C6-C24芳基的至少一个基团与酯连接链相连的部分或其重复单元。构成连接链的(聚)酯(多)醇的例子包括:用ε-己内酯、γ-丁内酯、δ-戊内酯和甲基戊内酯改性的(聚)亚烷基二醇如聚乙二醇,聚丙二醇,聚丁二醇,聚四亚甲基二醇,乙二醇,丙烷二醇,亚丙基二醇,四亚甲基二醇,五亚甲基二醇,己二醇,新戊基二醇,甘油,三羟甲基丙烷,季戊四醇,二甘油,双三羟甲基丙烷,双季戊四醇等;脂族聚酯多元醇,它们是通过用多元醇如新戊基二醇、甲基戊二醇等来酯化脂族二羧酸如己二酸、二聚酸等所合成的;芳族聚酯多元醇,它们是通过用多元醇如新戊基二醇等来酯化芳族二羧酸如对苯二甲酸等所合成的;酯化合物,它是通过用二羧酸如富马酸、邻苯二甲酸、间苯二酸、衣康酸、己二酸、癸二酸、马来酸等来酯化多元醇如聚碳酸酯多元醇、丙烯酰基多元醇、聚四亚甲基六甘油基醚(由四氢呋喃改性的六甘油)等所获得的;具有多元醇基团的化合物,如通过多元醇如甘油与动植物脂肪酸酯的酯基转移作用获得的单酸甘油酯;等等。然而,对这些(聚)酯(多)醇没有特殊限制。
由通过(聚)醚(多)醇与C2-C6羧酸(术语“C2-C6-羧酸”在下文中简写为多羧酸)的酯化作用而获得的在末端具有多羧酸残基的(多)羧酸{(聚)醚(多)醇}酯表示的连接链具有平均分子量100至100,000,并且包括其中选自直链或支链C2-C24亚烷基、C3-C24脂环族基团和C6-C24芳基的至少一个基团与醚连接链相连的部分或包括包含该部分的重复单元。构成连接链的、在端部具有多羧酸的(多)羧酸{(聚)醚(多)醇}酯的例子包括,通过多羧酸如琥珀酸、己二酸、邻苯二甲酸、六氢化邻苯二甲酸、四氢化邻苯二甲酸、富马酸、间苯二酸、衣康酸、癸二酸、马来酸、偏苯三酸、1,2,4,5-苯四酸、苯五羧酸、苯六羧酸、柠檬酸、四氢呋喃四羧酸、环己烷三羧酸等与以上公开的(聚)醚(多)醇等的酯化反应所获得的在端部具有多羧酸的(多)羧酸{(聚)醚(多)醇}酯。然而,对这些酯没有特别的限制。
由通过(聚)酯(多)醇和多羧酸的酯化获得的在端部具有多羧酸残基的(多)羧酸{(聚)酯(多)醇}酯表示的连接链具有平均分子量100至100,000,并且包括其中选自直链或支链C2-C24亚烷基、C3-C24脂环族基和C6-C24芳基的至少一个基团与醚和酯连接链相连的部分或包括包含该部分的重复单元。构成连接链的、在端部具有多羧酸的(多)羧酸{(聚)酯(多)醇}酯的例子包括通过多羧酸如琥珀酸、己二酸、邻苯二甲酸、六氢化邻苯二甲酸、四氢化邻苯二甲酸、富马酸、间苯二酸、衣康酸、癸二酸、马来酸、偏苯三酸、1,2,4,5-苯四酸、苯五羧酸、苯六羧酸、柠檬酸、四氢呋喃四羧酸、环己烷三羧酸等与以上公开的(聚)酯(多)醇等的酯化反应所获得的在端部具有多羧酸的(多)羧酸{(聚)酯(多)醇}酯。然而,对这些酯没有特别的限制。
由聚环氧化合物的开环反应获得的平均分子量为100至100,000的连接链,包括其中选自直链或支链C2-C24亚烷基、C3-C24脂环族基和C6-C24芳基的至少一个基团与醚连接链相连的部分或包括包含该部分的重复单元等。然而,对这些连接链没有特别的限制。形成连接链的(聚)环氧化物的例子包括:通过(甲基)表氯醇与双酚A、双酚F、它们的环氧乙烷改性产物、它们的环氧丙烷改性产物之间的反应所合成的表氯醇改性双酚型环氧树脂;由(甲基)表氯醇与氢化双酚A和氢化双酚F之间的反应及与由环氧乙烷改性或环氧丙烷改性的氢化双酚A和双酚F的反应所合成的表氯醇改性氢化双酚型环氧树脂;环氧-线型酚醛清漆树脂;从苯酚、双酚等与(甲基)表氯醇的反应获得的化合物;芳族环氧树脂如对苯二甲酸、间苯二酸、1,2,4,5-苯四酸等的缩水甘油基酯;从二醇如(聚)乙二醇,(聚)丙二醇,(聚)丁二醇,(聚)四亚甲基二醇,新戊基二醇,及其烯化氧改性二醇所合成的聚缩水甘油基醚;从脂肪族多元醇如三羟甲基丙烷,三羟甲基乙烷,甘油,二甘油,赤藓醇,季戊四醇,山梨糖醇,1,4-丁二醇,1,6-己二醇等,及其烯化氧改性的脂族多元醇所合成的聚缩水甘油基醚;从己二酸、癸二酸、马来酸、衣康酸等合成的缩水甘油基酯;从多元醇与多羧酸合成的聚酯多元醇的缩水甘油醚;共聚物如(甲基)丙烯酸缩水甘油基酯和(甲基)丙烯酸甲基缩水甘油基酯;脂肪族环氧树脂如高级脂肪酸、环氧化亚麻子油、环氧化大豆油、环氧化蓖麻油、环氧化的聚丁二烯等的缩水甘油基酯,等等。然而,对这些(聚)环氧化物没有特别的限制。
在连接链中,R2表示,以及优选是(聚)醚和(聚)酯连接链,它们具有平均分子量100至100,000并包括含有C2-C24直链或支化亚烷基、具有羟基的C2-C24亚烷基和/或C6-C24芳基的重复单元。
用于本发明的活性的能量可固化组合物中的、由结构式(1)表示的马来酰亚胺衍生物能够由众所周知的技术,从例如具有羧基的马来酰亚胺化合物与可与羧基反应的化合物之间的反应或从具有羟基的马来酰亚胺化合物与具有羧基的化合物之间的反应合成。
具有羧基的马来酰亚胺化合物能够由众所周知的技术从由下面反应式表示的马来酸酐与伯氨基羧酸的反应合成(例如参见D.H.Rich等人,Journal of Medical Chemistry,18卷,pp1004-10,1975)。
适合用于此类合成中的氨基羧酸的例子包括天门冬酰胺,丙氨酸,β-丙氨酸,精氨酸,异亮氨酸,氨基乙酸,谷氨酰胺,色氨酸,苏氨酸,缬氨酸,苯丙氨酸,homophenylalanine,α-甲基苯丙氨酸,赖氨酸,亮氨酸,环亮氨酸,3-氨基丙酸,α-氨基丁酸,4-氨基丁酸,氨基戊酸,6-氨基己酸,7-氨基庚酸,2-氨基辛酸,3-氨基辛酸,6-氨基辛酸,8-氨基辛酸,2-氨基壬酸,4-氨基壬酸,9-氨基壬酸,2-氨基癸酸,9-氨基癸酸,10-氨基癸酸,2-氨基十一酸,10-氨基十一酸,11-氨基十一酸,2-氨基月桂酸,11-氨基月桂酸,12-氨基月桂酸,2-氨基十三酸,13-氨基十三酸,2-氨基肉豆蔻酸,14-氨基肉豆蔻酸,2-氨基十五酸,15-氨基十五酸,2-氨基棕榈酸,16-氨基棕榈酸,2-氨基十七酸,17-氨基十七酸,2-氨基硬脂酸,18-氨基硬脂酸,2-氨基二十酸,20-氨基二十酸,氨基环己烷甲酸,氨基甲基环己烷甲酸,2-氨基-3-丙酸,3-氨基-3-苯基丙酸,等等。然而,对这些伯氨基羧酸没有特别的限制,因为实际上能够使用任何伯氨基羧酸。还有,吡咯烷酮,内酰胺如δ-戊内酰胺、ε-己内酰胺等也可以使用。
可与羧基反应的化合物的例子包括具有2-6个官能团和平均分子量为100-100,000的多元醇或聚环氧化合物,它们包括其中选自直链亚烷基、支链亚烷基、脂环族基团和芳族基团的至少一个连接基团与醚键和/或酯键相连的部分或重复单元。
对具有羧基的马来酰亚胺化合物和多元醇(可与羧基反应的一种化合物)之间的反应没有特别的限制。而且,由结构式(1)表示的马来酰亚胺衍生物能够按照Organic Synthesis Collective Volume(C.E.Rehberg等人,第3卷,pp 46,1955)中公开的众所周知的方式来合成。然而,优选的是该反应在环境或减压下进行,温度从室温到1 50℃,同时脱水并使用催化剂。该催化剂的例子包括酸催化剂如硫酸,磷酸,甲磺酸,苯磺酸,对-甲苯磺酸,强酸性阳离子交换树脂等。催化剂的用量应该在0.01-10wt.%范围内,基于原料的总重量。而且,与水共沸的有机溶剂也可用作该反应中的溶剂。与水共沸的有机溶剂的例子包括甲苯,苯,乙酸丁酯,乙酸乙酯,二异丙醚,二丁醚,等等。
对具有羧基的马来酰亚胺化合物与聚环氧化合物(它是可与羧基反应的一种化合物)之间的反应没有特别的限制。还有,由通式(1)表示的马来酰亚胺衍生物能够按照日本专利申请JP-A-4228529中公开的众所周知的方式来合成。然而,优选的是该反应在室温至150℃范围内的温度下、使用催化剂来进行。催化剂的例子包括咪唑类如2-甲基咪唑等;季铵盐如四甲基氯化铵,三甲基苄基氯化铵,四甲基溴化铵等;胺类如三甲胺,三乙胺,苄基甲基胺,三丁基胺等;膦类如三苯基膦,三环己基膦等;月桂酸盐如月桂酸二丁基锡盐等;碱性碱金属盐如乙酸钾,磷酸三钾,丙烯酸钠,甲基丙烯酸钠等;碱金属的醇盐如甲醇钠,乙醇钾等;阴离子交换树脂等。该催化剂的量应该在10至10,000ppm范围内,基于原料的总重量。
而且,不包括反应活性氢的有机溶剂也可用作反应中的溶剂。不包括反应活性氢的有机溶剂的例子包括芳族烃如甲苯、乙苯、1,2,3,4-四氢化萘、异丙基苯、二甲苯等;酮如丙酮、丁酮、甲基异丁基酮、环己酮等;酯如甲酸酯,乙酸甲酯,乙酸乙酯,乙酸正丁酯和类似物;等等。
用作可与羧基反应的化合物的多元醇的例子包括,例如,聚亚烷基二醇,如聚乙二醇,聚丙二醇,聚丁二醇,聚四亚甲基二醇等;亚烷基二醇如乙二醇、丙烷二醇、亚丙基二醇、丁烷二醇、亚丁基二醇、己烷二醇、新戊基二醇、甘油、三羟甲基丙烷、季戊四醇、二甘油、双三羟甲基丙烷、双季戊四醇等用环氧乙烷、环氧丙烷、环氧丁烷、四氢呋喃、ε-羟基己酸内酯、γ-丁内酯,δ-戊内酯和甲基戊内酯改性的一种改性亚烷基二醇;脂肪族多元醇如环氧乙烷与环氧丙烷的共聚物,亚丙基二醇与四氢呋喃的共聚物,乙二醇与四氢呋喃的共聚物,聚异戊二烯二醇,氢化的聚异戊二烯二醇,聚丁二烯二醇,氢化的聚丁二烯二醇等;脂族聚酯多元醇,它们是脂族二羧酸如己二酸和二聚酸与多元醇如新戊基二醇和甲基戊烷二醇等的酯化反应产物;芳族聚酯多元醇,它们是芳族二羧酸如对苯二甲酸与多元醇如新戊基二醇的酯化反应产物;聚碳酸酯多元醇;酰基多元醇;多羟基醇如聚四亚甲基六甘油醚(四氢呋喃改性的六甘油);含有单羟基或多羟基并在上述多羟基醇的端部有醚基团的化合物;由上述多羟基醇与二羧酸如富马酸、邻苯二甲酸、间苯二酸、衣康酸、己二酸、癸二酸、马来酸等的酯化反应获得的含有多羟基的化合物;由含有多羟基的化合物如甘油与动植物脂肪酸酯的酯基转移反应获得的含有多羟基的化合物。任何多元醇都可以使用,如果它们在分子中含有2至6个羟基的话。
用作可与羧基反应的化合物的聚环氧化物的例子包括,例如,被表氯醇改性的双酚型环氧树脂,它们是通过(甲基)表氯醇与双酚A、双酚F及其被环氧乙烷、环氧丙烷等改性的化合物之间的反应合成的;由表氯醇改性的氢化的双酚型环氧树脂和环氧Novolak树脂(Novolak是位于德克萨斯州Houston的Shell Company的注册商标),它们是由(甲基)表氯醇与氢化双酚A、氢化双酚F及其被环氧乙烷、环氧丙烷等改性的化合物之间的反应合成的;(甲基)表氯醇与苯酚和双酚的反应产物;芳族环氧树脂如对苯二甲酸、间苯二酸和pyrrolitic酸的缩水甘油基酯;二醇如(聚)乙二醇、(聚)丙二醇、(聚)丁二醇、(聚)四亚甲基二醇以及它们的烯化氧改性产物的聚缩水甘油基醚;被脂族多羟基醇如三羟甲基丙烷、三羟甲基乙烷、甘油、二甘油、赤藓醇、季戊四醇、山梨糖醇、1,4-丁二醇、1,6-己二醇以及它们的烯化氧改性化合物改性的缩水甘油基醚;羧酸如己二酸、癸二酸、马来酸和衣康酸的缩水甘油基酯;由多羟基醇和多羧酸制得的聚酯多元醇的缩水甘油基醚;(甲基)丙烯酸缩水甘油基酯和(甲基)丙烯酸甲基缩水甘油基酯的共聚物;脂肪族环氧树脂如高级脂肪酸、环氧化亚麻子油、环氧化大豆油、环氧化蓖麻油和环氧化聚丁二烯的缩水甘油基酯。
用于本发明的活性能量可固化组合物中的由结构式(1)表示的马来酰亚胺衍生物也能够由具有羟基的马来酰亚胺化合物与具有羧基的化合物反应来合成。
而且,具有羟基的马来酰亚胺化合物能够由马来酰亚胺和甲醛来合成,由以下反应式表示:
或通过使用马来酸酐和伯氨基醇由众所周知的技术来合成,由以下反应式表示:
(对于详细的合成实施例,参见U.S.专利2526517和日本专利申请JP-A-2-268155)。
伯氨基醇的例子包括2-氨基乙醇,1-氨基-2-丙醇,3-氨基-1-丙醇,2-氨基-2-甲基-1-丙醇,2-氨基-3-苯基-1-丙醇,4-氨基-1-丁醇,2-氨基-1-丁醇,2-氨基-3-甲基-1-丁醇,2-氨基-4-甲硫基-1-丁醇,2-氨基-1-戊醇,5-氨基-1-戊醇,(1-氨基环戊烷)甲醇,6-氨基-1-己醇,2-氨基-1-己醇,7-氨基-1-庚醇,2-(2-氨基乙氧基)乙醇,N-(2-氨基乙基)乙醇胺,4-氨基-1-哌嗪乙醇,2-氨基-1-苯基乙醇,2-氨基-3-苯基-1-丙醇,1-氨甲基-1-环己醇,氨基三甲基环己醇等。然而,对这些伯氨基醇没有特别的限制。任何伯氨基醇都能够使用。
可与羟基反应的化合物的例子包括多羧酸,该多羧酸在一个分子中有醚键和/或酯键,其平均分子量为100至100,000并包括其中选自直链亚烷基、支链亚烷基基团、脂环族基团和芳基的至少一个连接基团与醚键和/或酯键相连的部分或重复单元。
对于具有羟基的马来酰亚胺化合物和具有羧基的化合物之间的反应没有特别的限制。还有,由结构式(1)表示的马来酰亚胺衍生物能够按照Organic Synthesis Collective Volume(C.E.Rehberg等人,第3卷,pp 46,1955)中公开的众所周知的方式来合成。然而,优选的是该反应在环境或减压下进行,在室温到150℃范围内的温度下,同时脱水和使用催化剂。催化剂的例子包括酸催化剂如硫酸,磷酸,甲磺酸,苯磺酸,对-甲苯磺酸,强酸性阳离子交换树脂等。催化剂的用量应该在0.01至10wt.%范围内,基于原料的总重量。
在这种情况下,作为反应的溶剂,有可能使用与水共沸的有机溶剂。此类有机溶剂的例子包括甲苯,苯,乙酸丁酯,乙酸乙酯,二异丙醚,二丁醚,等等。
对于以上反应的任何情况,优选的是使用自由基聚合抑制剂,为的是抑制马来酰亚胺基团的自由基聚合。自由基聚合抑制剂包括,例如,苯酚衍生物如氢醌,叔丁基氢醌,甲氧基氢醌,2,4-二甲基-6-叔丁基苯酚,儿茶酚,叔丁基儿茶酚等;胺类如吩噻嗪、对苯二胺、二苯胺和类似物;铜配合物如铜-二硫代氨基甲酸二甲酯,铜-二硫代氨基甲酸二乙酯,铜-二硫代氨基甲酸二丁酯等。这些抑制剂可以单独或以两种或多种的混合物使用。优选的是选择在10-10,000ppm范围内的抑制剂用量,相对于原料的总重量。
作为具有醚键和酯键化合物的多羧酸的例子包括,例如,但不限于,由二羧酸如富马酸、邻苯二甲酸、间苯二酸、衣康酸、己二酸、癸二酸、马来酸、琥珀酸、六氢化邻苯二甲酸、四氢化邻苯二甲酸、1,2,4,5-苯四酸和上述二羧酸与上述多元醇的酯化所获得的多羧酸,并由下式表示:
HOOC-X′-COO-Y′OOC-X′-COOH)n
其中X′表示二羧酸残基,γ′表示多元醇残基,和n是1到5的整数。
由结构式(1)表示的并用于本发明的活性能量可固化组合物中的马来酰亚胺衍生物是通过上述制备方法,但不限于本文所述的方法来获得的。
还有可能添加可与马来酰亚胺基团共聚合的化合物,一起用于根据本发明的含有马来酰亚胺衍生物的活性能量可固化组合物中。可与马来酰亚胺基团共聚合的化合物的实际例子例如是具有各种不饱和双键的化合物。此类化合物包括,例如,不由以上结构式(1)表示的马来酰亚胺衍生物,(甲基)丙烯酰基衍生物,(甲基)丙烯酰胺衍生物,乙烯基酯衍生物,乙烯基羧酸酯衍生物,苯乙烯衍生物以及不饱和的聚酯。
不由结构式(1)表示的马来酰亚胺衍生物的例子包括,例如,但不限于:
单官能脂肪族马来酰亚胺如N-甲基马来酰亚胺,N-乙基马来酰亚胺,N-丙基马来酰亚胺,N-正丁基马来酰亚胺,N-叔丁基马来酰亚胺,N-戊基马来酰亚胺,N-己基马来酰亚胺,N-月桂基马来酰亚胺,2-马来酰亚胺乙基-乙基-碳酸酯,2-马来酰亚胺乙基-异丙基-碳酸酯,和N-乙基-(2-马来酰亚胺乙基)氨基甲酸酯;单官能脂环族马来酰亚胺如N-环己基马来酰亚胺;芳族单官能马来酰亚胺如N-苯基马来酰亚胺,N-2-甲基苯基马来酰亚胺,N-2-乙基苯基马来酰亚胺,N-(2,6-二乙基苯基)马来酰亚胺,N-2-氯苯基马来酰亚胺,和N-(4-羟苯基)马来酰亚胺;
脂肪族双马来酰亚胺如N,N′-亚甲基双马来酰亚胺,N,N′-亚乙基双马来酰亚胺,N,N′-三亚甲基双马来酰亚胺,N,N′-六亚甲基双马来酰亚胺,N,N′-十二亚甲基双马来酰亚胺,聚丙二醇-双(3-马来酰亚胺丙基)醚,四甘醇-双(3-马来酰亚胺丙基)醚,和双(2-马来酰亚胺乙基)碳酸酯;
脂环族双马来酰亚胺如1,4-双马来酰亚胺环己烷和异佛尔酮双脲烷双(N-乙基马来酰亚胺);
芳族双马来酰亚胺如N,N′-(4,4′-二苯甲烷)双马来酰亚胺,N,N′-(4,4′-二苯氧基)双马来酰亚胺,N,N′-对苯双马来酰亚胺,N,N′-间苯双马来酰亚胺,N,N′-2,4-甲苯双马来酰亚胺,N,N′-2,6-甲苯双马来酰亚胺,N,N′-[4,4′-双(3,5-二甲基苯基)甲烷]双马来酰亚胺,N,N′-[4,4′-双(3,5-二乙基苯基)甲烷]双马来酰亚胺;
由羟基马来酰亚胺与各种(多)异氰酸酯的脲烷化反应获得的(聚)脲烷(聚)马来酰亚胺衍生物,如通过羟乙基马来酰亚胺与由3摩尔异佛尔酮二异氰酸酯和1摩尔的环氧丙烷改性的甘油之间的反应所生产的三异氰酸酯的脲烷化反应所获得的马来酰亚胺衍生物;
通过羟甲基马来酰亚胺与由2摩尔2,4-甲苯二异氰酸酯和1摩尔聚四亚甲基二醇之间的反应所生产的二异氰酸酯的脲烷化反应所获得的马来酰亚胺衍生物;和
具有丙烯酰氧基或甲基丙烯酰氧基的化合物能够被分类成,但不限于:聚酯(甲基)丙烯酸酯;脲烷(甲基)丙烯酸酯;环氧树脂(甲基)丙烯酸酯;(聚)醚(甲基)丙烯酸酯;(甲基)丙烯酸烷基酯或(甲基)丙烯酸亚烷基二醇酯;具有芳族环的(甲基)丙烯酸酯和;具有脂环族环的(甲基)丙烯酸酯。
在以上分类中的名称是作为各化合物的通用术语使用的,这些化合物能够一起用于本发明的活性能量可固化组合物。聚酯(甲基)丙烯酸酯通常表示在主链中具有至少一个酯键的(甲基)丙烯酸酯;脲烷(甲基)丙烯酸酯通常表示在主链中具有至少一个脲烷键的(甲基)丙烯酸酯;环氧树脂(甲基)丙烯酸酯通常表示由(甲基)丙烯酸和具有一个和一个以上官能团的环氧化物之间的反应获得的(甲基)丙烯酸酯;(聚)醚(甲基)丙烯酸酯通常表示在主链中具有至少一个醚键的(甲基)丙烯酸酯;(甲基)丙烯酸烷基酯或(甲基)丙烯酸亚烷基二醇酯通常表示包括由线性烷基、支化烷基、线性亚烷基或支化亚烷基构成的主链以及具有卤素原子和/或羟基的侧链或端基的(甲基)丙烯酸酯;具有芳族环的(甲基)丙烯酸酯通常表示在主链或侧链中具有芳族环的(甲基)丙烯酸酯;具有脂环族环基团的(甲基)丙烯酸酯通常表示在主链或侧链中具有可包括氧原子或氮原子作为结构单元的脂环族基团的(甲基)丙烯酸酯。
能够在本发明的活性能量可固化组合物中一起使用的(聚)酯(甲基)丙烯酸酯的例子包括,例如,但不限于:单官能(聚)酯(甲基)丙烯酸酯如脂环族-改性的新戊基二醇(甲基)丙烯酸酯,己内酯-改性的2-羟乙基(甲基)丙烯酸酯,环氧乙烷-和/或环氧丙烷-改性的邻苯二甲酸酯(甲基)丙烯酸酯,环氧乙烷-改性的琥珀酸酯(甲基)丙烯酸酯,己内酯-改性的四氢化糠基(甲基)丙烯酸酯;新戊酸酯新戊基二醇二(甲基)丙烯酸酯,己内酯-改性的羟基新戊酸酯新戊基二醇二(甲基)丙烯酸酯,表氯醇-改性的邻苯二甲酸酯二(甲基)丙烯酸酯;由1摩尔以上的环内酯如ε-己内酯、γ-丁内酯、δ-戊内酯或甲基戊内酯加成到1摩尔三羟甲基丙烷或甘油上所获得的三元醇的单、二或三(甲基)丙烯酸酯;由1摩尔以上环内酯如ε-己内酯、γ-丁内酯、δ-戊内酯或甲基戊内酯加成到1摩尔季戊四醇或双三羟甲基丙烷上所获得的三元醇的单、二、三或四(甲基)丙烯酸酯;由1摩尔以上环内酯如ε-己内酯、γ-丁内酯、δ-戊内酯或甲基戊内酯加成到1摩尔双季戊四醇上所获得的多元醇如三元醇、四元醇、五元醇或六元醇的单-或多-(甲基)丙烯酸酯;由二元醇组分如聚乙二醇、聚丙二醇、(聚)四亚甲基二醇、(聚)丁二醇、(聚)戊烷二醇、(聚)甲基戊烷二醇和(聚)己烷二醇和多元酸如马来酸、富马酸、琥珀酸、己二酸、邻苯二甲酸、六氢化邻苯二甲酸、四氢化邻苯二甲酸、衣康酸、柠康酸、hettic酸、氯菌酸,二聚酸,链烯基琥珀酸、癸二酸、壬二酸、2,2,4-三甲基己二酸、1,4-环己烷二羧酸、对苯二甲酸、2-磺酸钠对苯二甲酸、2-磺酸钾对苯二甲酸、间苯二酸、5-磺酸钠间苯二甲酸、5-磺酸钾间苯二甲酸、邻苯二甲酸、4-磺基邻苯二甲酸、1,10-十亚甲基二羧酸、己二烯二酸、草酸、丙二酸、戊二酸、偏苯三酸、1,2,4,5-苯四酸组成的聚酯二醇的(甲基)丙烯酸酯;和由上述二醇组分、多元酸和环内酯改性的聚酯二醇如如ε-羟基己酸内酯、γ-丁内酯、δ-戊内酯或甲基戊内酯组成的多官能化(聚)酯(甲基)丙烯酸酯。
能够一起用于本发明的活性能量可固化组合物中的脲烷(甲基)丙烯酸酯是表示由具有至少一个丙烯酰氧基的羟基化合物和异氰酸酯化合物之间的反应获得的(甲基)丙烯酸酯的一般术语。脲烷(甲基)丙烯酸酯也可选自可用水稀释的脂族丙烯酸酯或芳族脲烷。
具有至少一个丙烯酰氧基的羟基化合物的例子包括,例如,(甲基)丙烯酸2-羟乙基酯,(甲基)丙烯酸2-羟丙基酯,(甲基)丙烯酸2-羟基丁基酯,(甲基)丙烯酸3-羟基丁基酯,(甲基)丙烯酸4-羟基丁基酯,环己烷二甲醇单(甲基)丙烯酸酯,聚乙二醇(甲基)丙烯酸酯,聚丙二醇(甲基)丙烯酸酯,二(甲基)丙烯酸(三羟甲基丙烷)酯,二(甲基)丙烯酸(三羟甲基乙烷)酯,三(甲基)丙烯酸季戊四醇酯或(甲基)丙烯酸酯与(甲基)丙烯酸缩水甘油基酯的加合物,具有羟基的(甲基)丙烯酸酯化合物如2-羟基-3-苯酚丙基(甲基)丙烯酸酯,和以上具有羟基的丙烯酸酯化合物与ε-己内酯的开环反应产物。
异氰酸酯化合物的例子包括,例如,芳族二异氰酸酯如对-亚苯基二异氰酸酯,间-亚苯基二异氰酸酯,对-亚二甲苯基二异氰酸酯,间-亚二甲苯基二异氰酸酯,2,4-亚甲苯基二异氰酸酯,2,6-亚甲苯基二异氰酸酯,4,4′-二苯基甲烷二异氰酸酯,3,3′-二甲基二苯基-4,4′-二异氰酸酯,3,3′-二乙基二苯基-4,4′-二异氰酸酯,和亚萘基二异氰酸酯;脂肪族或脂环族的二异氰酸酯如异佛尔酮二异氰酸酯,六亚甲基二异氰酸酯,4,4′-二环己基甲烷二异氰酸酯,氢化亚二甲苯基二异氰酸酯,降冰片烯二异氰酸酯,和赖氨酸二异氰酸酯;多异氰酸酯如一种以上类型的异氰酸酯的缩二脲产物和上述异氰酸酯的异氰酸酯三聚体;和由以上异氰酸酯与各种多元醇的酯化反应获得的多异氰酸酯。
用于生产多异氰酸酯的多元醇的例子包括,例如,(聚)亚烷基二醇如(聚)乙二醇,(聚)丙二醇,(聚)丁二醇,和(聚)四亚甲基二醇;由环氧乙烷、环氧丙烷、环氧丁烷、四氢呋喃、ε-己内酯、γ-丁内酯、δ-戊内酯或甲基戊内酯改性的亚烷基二醇,这类二醇比如有乙二醇、丙烷二醇、亚丙基二醇、四亚甲基二醇、五亚甲基二醇、己烷二醇、新戊基二醇、甘油、三羟甲基丙烷、季戊四醇、二甘油、双三羟甲基丙烷和双季戊四醇;脂肪族多元醇如环氧乙烷和环氧丙烷的共聚物,丙二醇和四氢呋喃的共聚物,乙二醇和四氢呋喃的共聚物,聚异戊二烯二醇,氢化的聚异戊二烯二醇,聚丁二烯二醇,和氢化的聚丁二烯二醇;由脂族二羧酸如己二酸和二聚酸与多元醇如新戊基二醇和甲基戊烷二醇之间的酯化反应获得的脂族聚酯多元醇;由芳族二羧酸如对苯二甲酸与多元醇如新戊基二醇之间的酯化反应获得的芳族聚酯多元醇;聚碳酸酯多元醇;丙烯酰基多元醇;多羟基醇如聚四亚甲基六甘油基醚(由四氢呋喃改性的六甘油);在端部有醚基的以上化合物的单或多羟基化合物;由具有多羟基的化合物与二羧酸如富马酸、邻苯二甲酸、间苯二酸、衣康酸、己二酸、癸二酸、和马来酸的酯化反应获得的多羟基化合物;含有多羟基的化合物,如通过具有多羟基的化合物如甘油与动物或植物脂肪酸的酯类之间的酯基转移反应获得的单酸甘油酯。
能够一起用于本发明的活性能量可固化组合物中的环氧树脂(甲基)丙烯酸酯是表示通过具有一个以上官能团的环氧化物和(甲基)丙烯酯的反应所获得的(甲基)丙烯酸酯的通用术语。作为环氧树脂(甲基)丙烯酸酯的原料的环氧化物包括,例如,但不限于:表氯醇-改性的氢化双酚型环氧树脂,由(甲基)表氯醇和化合物如氢化双酚A、氢化双酚S、氢化双酚F及其用环氧乙烷或环氧丙烷改性的化合物合成;脂环族环氧树脂如3,4-环氧基环己烷羧酸3,4-环氧基环己基甲基酯,己二酸双(3,4-环氧基环己基)酯;脂环族环氧化物如含有杂环的环氧树脂如异氰脲酸三缩水甘油基酯;由(甲基)表氯醇和化合物如双酚A、双酚S和双酚F及其用环氧乙烷或环氧丙烷改性的化合物之间的反应合成的表氯醇-改性的双酚型环氧树脂;苯酚Novolak型环氧树脂;甲酚Novolak型环氧树脂;由双环戊二烯和各种类型酚树脂的反应获得的双环戊二烯改性的酚树脂的环氧树脂;2,2′,6,6′-四甲基双酚的芳族环氧化化合物;芳族环氧化物如苯基缩水甘油基醚;二醇化合物如(聚)乙二醇、(聚)丙二醇、(聚)丁二醇、(聚)四亚甲基二醇、新戊基二醇的(多)缩水甘油基醚;二醇用烯化氧改性的(聚)缩水甘油基醚;脂肪族多羟基醇如三羟甲基丙烷、三羟甲基乙烷、甘油、二甘油、赤藓醇、季戊四醇、山梨糖醇、1,4-丁烷二醇、1,6-己烷二醇的(聚)缩水甘油基醚;脂族多羟基醇用亚烷基改性的(聚)缩水甘油基醚的亚烷基型环氧化物;羧酸如己二酸、癸二酸、马来酸和衣康酸的缩水甘油基酯;多羟基醇与多羧酸的聚酯多元醇的缩水甘油基醚;(甲基)丙烯酸缩水甘油基酯或(甲基)丙烯酸甲基缩水甘油基酯的共聚物;高级脂肪酸的缩水甘油基酯;脂肪族环氧树脂如环氧化亚麻子油、环氧化蓖麻油和环氧化聚丁二烯。
能够一起用于本发明的活性能量可固化组合物中的(聚)醚(甲基)丙烯酸酯包括,例如,但不限于:脂肪族环氧树脂丙烯酸酯,单官能(聚)醚(甲基)丙烯酸酯如(甲基)丙烯酸丁氧基乙基酯,丁氧基三亚乙基二醇(甲基)丙烯酸酯,表氯醇-改性的(甲基)丙烯酸丁基酯,(甲基)丙烯酸二环戊烯基氧基乙基酯,(甲基)丙烯酸2-乙氧基乙基酯,乙基卡必醇(甲基)丙烯酸酯,2-甲氧基(聚)乙二醇(甲基)丙烯酸酯,甲氧基(聚)丙二醇(甲基)丙烯酸酯,壬基苯氧基聚乙二醇(甲基)丙烯酸酯,壬基苯氧基聚丙二醇(甲基)丙烯酸酯,(甲基)丙烯酸苯氧基羟丙基酯,苯氧基(聚)乙二醇(甲基)丙烯酸酯,聚乙二醇单(甲基)丙烯酸酯,聚丙二醇单(甲基)丙烯酸酯,和聚乙二醇,聚丙二醇单(甲基)丙烯酸酯;亚烷基二醇二(甲基)丙烯酸酯如聚乙二醇二(甲基)丙烯酸酯,聚丙二醇二(甲基)丙烯酸酯,聚丁二醇二(甲基)丙烯酸酯,聚四亚甲基二醇二(甲基)丙烯酸酯;由(甲基)丙烯酸与脂肪族多元醇如环氧乙烷和环氧丙烷的共聚物、丙二醇和四氢呋喃的共聚物、乙二醇和四氢呋喃的共聚物、聚异戊二烯二醇、氢化的聚异戊二烯二醇、聚丁二烯二醇、氢化的聚丁二烯二醇衍生的多官能(甲基)丙烯酸酯;由丙烯酸与多羟基醇如聚四亚甲基六甘油基醚(四氢呋喃-改性的六甘油)衍生的多官能(甲基)丙烯酸酯;由1摩尔或1摩尔以上的环醚如环氧乙烷、环氧丙烷、环氧丁烷和/或四氢呋喃加成到1摩尔新戊基氧化物上所获得的二醇的二(甲基)丙烯酸酯;烯化氧-改性的双酚类如双酚A、双酚F和双酚S的二(甲基)丙烯酸酯;烯化氧-改性的氢化双酚类如氢化双酚A、氢化双酚F、氢化双酚S的二(甲基)丙烯酸酯;烯化氧-改性的三苯酚的二(甲基)丙烯酸酯;烯化氧-改性的氢化三苯酚的二(甲基)丙烯酸酯;烯化氧-改性的p,p′-双酚的二(甲基)丙烯酸酯;烯化氧-改性的氢化双酚的二(甲基)丙烯酸酯;烯化氧-改性的p,p′-二羟基二苯甲酮的二(甲基)丙烯酸酯;由1摩尔或1摩尔以上环氧乙烷、环氧丙烷、环氧丁烷和/或环醚如四氢呋喃加成到1摩尔三羟甲基丙烷或甘油上所获得的三醇的单-、二-和三(甲基)丙烯酸酯;由1摩尔或1摩尔以上环氧乙烷、环氧丙烷、环氧丁烷和/或环醚如四氢呋喃加成到1摩尔季戊四醇、双三羟甲基丙烷或高度烷氧基化的三羟甲基丙烷三丙烯酸酯上所获得的单-、二-,三-或四(甲基)丙烯酸酯;多羟基醇如三醇、四醇、五醇或六醇的单官能(聚)醚(甲基)丙烯酸酯或多官能(聚)醚(甲基)丙烯酸酯,如由1摩尔或1摩尔以上环氧乙烷、环氧丙烷、环氧丁烷和/或环醚如四氢呋喃加成到1摩尔双季戊四醇上所获得的单-或多(甲基)丙烯酸酯。
可一起用于本发明的活性能量可固化组合物中的(甲基)丙烯酸烷基酯或(甲基)丙烯酸亚烷基酯包括,例如,但不限于:单官能(甲基)丙烯酸酯如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸异丙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸戊酯、(甲基)丙烯酸异戊酯、(甲基)丙烯酸新戊酯、(甲基)丙烯酸己酯、(甲基)丙烯酸庚酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸辛酯、(甲基)丙烯酸异辛酯、(甲基)丙烯酸壬酯、(甲基)丙烯酸癸酯、(甲基)丙烯酸十二烷酯、(甲基)丙烯酸十三烷酯、(甲基)丙烯酸十五烷酯、(甲基)丙烯酸肉豆蔻醇酯、(甲基)丙烯酸棕榈醇酯、(甲基)丙烯酸硬脂醇酯、(甲基)丙烯酸橙花醇酯、(甲基)丙烯酸香叶醇酯、(甲基)丙烯酸法呢醇酯、(甲基)丙烯酸十六烷酯、(甲基)丙烯酸十八烷酯、(甲基)丙烯酸二十二烷酯和(甲基)丙烯酸反式-2-己烯酯;脂族二醇的二(甲基)丙烯酸酯如二(甲基)丙烯酸乙二醇酯,二(甲基)丙烯酸丙二醇酯,二(甲基)丙烯酸1,2-丁二醇酯,二(甲基)丙烯酸1,3-丁二醇酯,二(甲基)丙烯酸1,4-丁二醇酯,二(甲基)丙烯酸1,6-己二醇酯,二(甲基)丙烯酸新戊基二醇酯,二(甲基)丙烯酸2-甲基-1,8-辛二醇酯,二(甲基)丙烯酸1,9-壬二醇酯,和二(甲基)丙烯酸1,10-癸二醇酯;多羟基醇如三羟甲基丙烷的单(甲基)丙烯酸酯或多(甲基)丙烯酸酯(下文中,术语“多”用作多官能化物包括二、三、四和多-化合物在内的通用术语,如三羟甲基丙烷的单(甲基)丙烯酸酯、二(甲基)丙烯酸酯和三(甲基)丙烯酸酯),和多羟基醇如三醇、四醇和六醇例如甘油、季戊四醇、双三羟甲基丙烷和双季戊四醇的单(甲基)丙烯酸酯或多(甲基)丙烯酸酯;具有羟基的(甲基)丙烯酸酯,如(甲基)丙烯酸2-羟乙基酯,(甲基)丙烯酸2-羟丙基酯,(甲基)丙烯酸4-羟丁基酯,(甲基)丙烯酸3-氯-2-羟乙基酯;具有溴原子的(甲基)丙烯酸酯如(甲基)丙烯酸2,3-二溴丙基酯,(甲基)丙烯酸三溴苯基酯,环氧乙烷改性的(甲基)丙烯酸三溴苯基酯,环氧乙烷改性的四溴双酚A二(甲基)丙烯酸酯;具有氟原子的(甲基)丙烯酸酯如(甲基)丙烯酸三氟乙基酯,(甲基)丙烯酸五氟丙基酯,(甲基)丙烯酸四氟丙基酯,(甲基)丙烯酸八氟戊基酯,(甲基)丙烯酸十氟庚基酯,(甲基)丙烯酸十六氟壬基酯,(甲基)丙烯酸六氟丁基酯,(甲基)丙烯酸3-全氟丁基-2-羟丙基酯,(甲基)丙烯酸3-全氟己基-2-羟丙基酯,(甲基)丙烯酸3-全氟辛基-2-羟丙基酯,(甲基)丙烯酸3-(全氟-5-甲基己基)-2-羟丙基酯,(甲基)丙烯酸3-(全氟-7-甲基辛基)-2-羟丙基酯和(甲基)丙烯酸3-(全氟-8-甲基癸基)-2-羟丙基酯。
能够一起用于本发明的活性能量可固化组合物中的具有芳族基团的(甲基)丙烯酸酯包括,例如,但不限于:单官能(甲基)丙烯酸酯如(甲基)丙烯酸苯基酯,丙烯酸苄基酯;和二(甲基)丙烯酸酯如双酚A二丙烯酸酯,双酚F二丙烯酸酯,双酚S二丙烯酸酯。
能够一起用于本发明的活性能量可固化组合物中的具有脂环族基团的(甲基)丙烯酸酯包括,例如,但不限于:具有脂环族结构的单官能(甲基)丙烯酸酯,如(甲基)丙烯酸环己基酯,(甲基)丙烯酸环戊基酯,(甲基)丙烯酸环庚基酯,(甲基)丙烯酸双环庚基酯,(甲基)丙烯酸异冰片基酯,二(甲基)丙烯酸双环戊基酯,(甲基)丙烯酸三环癸基酯,(甲基)丙烯酸双环戊烯基酯,(甲基)丙烯酸降冰片基酯,(甲基)丙烯酸双环辛基酯,(甲基)丙烯酸三环庚基酯,和胆甾族骨架取代的(甲基)丙烯酸酯;氢化双酚如氢化双酚A、氢化双酚F、氢化双酚S的二(甲基)丙烯酸酯,氢化三酚类如氢化三苯酚的二(甲基)丙烯酸酯,和氢化p,p′-双酚的二(甲基)丙烯酸酯;具有环状结构的多官能(甲基)丙烯酸酯,如双环戊烷型二(甲基)丙烯酸酯如“Kayarad R684”(可购自Nihon KayakuCo.,Japan),二(甲基)丙烯酸三环癸烷二甲醇酯,双酚芴二羟基(甲基)丙烯酸酯(bisphenolfluorene dihydroxy(meth)acrylate);和具有氧原子和/或氮原子的丙烯酸脂环族基酯,如(甲基)丙烯酸四氢化糠基酯和(甲基)丙烯酸吗啉子基乙基酯。
作为可一起用于本发明的活性能量可固化组合物中的具有丙烯酰基或甲基丙烯酰基的化合物,除了以上列举的化合物外,还可使用例如聚(甲基)丙烯酰基(甲基)丙烯酸酯如(甲基)丙烯酸聚合物和(甲基)丙烯酸缩水甘油基酯的反应产物,和(甲基)丙烯酸缩水甘油基酯聚合物和(甲基)丙烯酸的反应产物;具有氨基的(甲基)丙烯酸酯,如(甲基)丙烯酸二甲氨基乙基酯;异氰脲酸(甲基)丙烯酸酯类(isocyanul(meth)acrylates)如三((甲基)丙烯酰氧基乙基)异氰脲酸酯;磷酸肌酸(甲基)丙烯酸酯类(phosphagene(meth)acrylate)如六[(甲基)丙烯酰氧基乙基)环三磷酸肌酸];具有聚硅氧烷骨架的(甲基)丙烯酸酯;(甲基)丙烯酸聚丁二烯二醇酯;和密胺(甲基)丙烯酸酯。在具有丙烯酰基和甲基丙烯酰基的这些化合物当中,优选使用具有1-6个丙烯酰基或甲基丙烯酰基的化合物。
能够一起用于本发明的活性能量可固化组合物中的(甲基)丙烯酰胺衍生物包括,例如,单官能(甲基)丙烯酰胺如N-异丙基(甲基)丙烯酰胺和多官能(甲基)丙烯酰胺如亚甲基双(甲基)丙烯酰胺。
可以一起用于本发明的活性能量可固化组合物中的具有乙烯基醚基团的化合物可被分成,但不限于,以下几组,其中:具有被选自氢原子、卤素原子、羟基和氨基的至少一个基团所取代端基的烷基乙烯基醚;具有被选自氢原子、卤素原子、羟基和氨基的至少一个基团所取代端基的环烷基乙烯基醚;选自单乙烯基醚、二乙烯基醚和多乙烯基醚的至少一种乙烯基醚,其中经过选自醚键、脲烷键和酯键的至少一个连接基,乙烯基醚基团与亚烷基相连,和其中乙烯基醚基团与有或没有取代基的从烷基、环烷基和芳族基团中选择的至少一个基团相连。
能够一起用于本发明的活性能量可固化组合物中的烷基乙烯基醚包括,例如,但不限于:甲基乙烯基醚,羟甲基乙烯基醚,氯甲基乙烯基醚,乙基乙烯基醚,2-羟乙基乙烯基醚,2-氯乙基乙烯基醚,二乙基氨基乙基乙烯基醚,丙基乙烯基醚,3-羟丙基乙烯基醚,2-羟丙基乙烯基醚,3-氯丙基乙烯基醚,3-氨基丙基乙烯基醚,异丙基乙烯基醚,丁基乙烯基醚,4-羟丁基乙烯基醚,异丁基乙烯基醚,4-氨基丁基乙烯基醚,戊基乙烯基醚,异戊基乙烯基醚,己基乙烯基醚,1,6-己二醇单乙烯基醚,庚基乙烯基醚,2-乙基己基乙烯基醚,辛基乙烯基醚,异辛基乙烯基醚,壬基乙烯基醚,异壬基乙烯基醚,癸基乙烯基醚,异癸基乙烯基醚,十二烷基乙烯基醚,异十二烷基乙烯基醚,十三烷基乙烯基醚,异十三烷基乙烯基醚,十五烷基乙烯基醚,异十五烷基乙烯基醚,十六烷基乙烯基醚,十八烷基乙烯基醚,亚甲基二醇二乙烯基醚,乙二醇二乙烯基醚,丙二醇二乙烯基醚,1,4-丁二醇二乙烯基醚,1,6-己二醇二乙烯基醚,环己二醇二乙烯基醚,三羟甲基丙烷三乙烯基醚,季戊四醇四乙烯基醚和己二酸双[(4-乙烯基氧基)丁基]酯。
能够一起用于本发明的活性能量可固化组合物中的环烷基乙烯基醚包括,例如,但不限于:环丙基乙烯基醚,2-羟基环丙基乙烯基醚,2-氯环丙基乙烯基醚,环丙基甲基乙烯基醚,环丁基乙烯基醚,3-羟基环丁基乙烯基醚,3-氯环丁基乙烯基醚,环丁基甲基乙烯基醚,环戊基乙烯基醚,3-羟基环戊基乙烯基醚,3-氯环戊基乙烯基醚,环戊基甲基乙烯基醚,环己基乙烯基醚,4-羟基环己基乙烯基醚,环己基甲基乙烯基醚,4-氨基环己基乙烯基醚,环己烷二醇单乙烯基醚,环己烷二甲醇单乙烯基醚,和环己烷二甲醇二乙烯基醚。
在能够一起用于本发明的活性能量可固化组合物中的包括其中乙烯基醚连接基与亚烷基相连和选自可有取代基的C2-C24烷基、C2-C24脂环族基团和C2-C24芳族基团的至少一个基团与选自醚键、脲烷键和酯键的连接基相连的单乙烯基醚、二乙烯基醚和多乙烯基醚在内的化合物当中,含有醚键的化合物的例子包括,例如,但不限于, 乙二醇甲基乙烯基醚,二甘醇单乙烯基醚,二甘醇甲基乙烯基醚,二甘醇二乙烯基醚,三甘醇单乙烯基醚,三甘醇甲基乙烯基醚,三甘醇二乙烯基醚,聚乙二醇单乙烯基醚,聚乙二醇甲基乙烯基醚,聚乙二醇二乙烯基醚,丙二醇甲基乙烯基醚,二丙二醇单乙烯基醚,二丙二醇甲基乙烯基醚,二丙二醇二乙烯基醚,三丙二醇单乙烯基醚,三丙二醇甲基乙烯基醚,三丙二醇二乙烯基醚,聚丙二醇单乙烯基醚,聚丙二醇甲基乙烯基醚,聚丙二醇二乙烯基醚,四亚甲基二醇甲基乙烯基醚,二(四亚甲基二醇)单乙烯基醚,二(四亚甲基二醇)甲基乙烯基醚,二(四亚甲基二醇)二乙烯基醚,三(四亚甲基二醇)单乙烯基醚,三(四亚甲基二醇)甲基乙烯基醚,三(四亚甲基二醇)二乙烯基醚,多(四亚甲基二醇)单乙烯基醚,多(四亚甲基二醇)甲基乙烯基醚,多(四亚甲基二醇)二乙烯基醚,1,6-己烷二醇甲基乙烯基醚,二(六亚甲基二醇)单乙烯基醚,二(六亚甲基二醇)甲基乙烯基醚,二(六亚甲基二醇)二乙烯基醚,三(六亚甲基二醇)单乙烯基醚,三(六亚甲基二醇)甲基乙烯基醚,三(六亚甲基二醇)二乙烯基醚,多(六亚甲基二醇)单乙烯基醚,多(六亚甲基二醇)甲基乙烯基醚,多(六亚甲基二醇)二乙烯基醚。
在分类到以上具有乙烯基醚连接基的化合物当中,具有脲烷连接基的化合物可通过在一个分子中有至少一个羟基的(聚)亚烷基二醇的单乙烯基醚和在一个分子中有至少一个异氰酸酯基团的化合物之间的脲烷化反应来获得。在这些化合物当中,(聚)亚烷基二醇的单乙烯基醚在分子中包括至少一个羟基,例如,2-羟乙基乙烯基醚,二甘醇单乙烯基醚,聚乙二醇单乙烯基醚,3-羟丙基乙烯基醚,2-羟基-2-甲基乙基乙烯基醚,二丙二醇单乙烯基醚,聚丙二醇单乙烯基醚,4-羟丁基乙烯基醚,和1,6-己二醇单乙烯基醚。
另一方面,在一个分子具有至少一个异氰酸酯基的化合物包括,例如,芳族二异氰酸酯如间-异丙烯基-α,α-二甲基苄基异氰酸酯,对-苯二异氰酸酯,间-苯二异氰酸酯,对-亚二甲苯基二异氰酸酯,间-亚二甲苯基二异氰酸酯,2,4-甲苯二异氰酸酯,2,6-甲苯二异氰酸酯,4,4′-二苯基甲烷二异氰酸酯,3,3′-二乙基二苯基-4,4′-二异氰酸酯,3,3′-二甲基二苯基-4,4′-二异氰酸酯,萘二异氰酸酯;以及脂肪族和脂环族异氰酸酯如丙基异氰酸酯,异佛尔酮二异氰酸酯,六亚甲基二异氰酸酯,4,4′-二环己基甲烷二异氰酸酯,氢化二甲苯二异氰酸酯,降冰片烯二异氰酸酯,赖氨酸二异氰酸酯。
也有可能使用异氰酸酯化合物如包括一个以上这些异氰酸酯单体的二聚体或三聚体,和使用由在一个分子中含有2个以上异氰酸酯基的异氰酸酯化合物和各种醇之间的脲烷化反应所获得的加合物。
各种醇能够用于获得加合物产物,如果醇含有至少一个羟基的话。虽然没有限制,优选的是使用平均分子量低于100,000的醇。此类醇的例子包括,例如,甲醇,乙醇,丙醇,异丙醇,丁醇,异丁醇,乙二醇,1,3-丙二醇,1,2-丙二醇,二甘醇,二丙二醇,新戊基二醇,1,3-丁二醇,1,4-丁二醇,1,6-己二醇,1,9-壬二醇,1,10-癸二醇,2,2′,4-三甲基-1,3-戊二醇,3-甲基-1,5-戊二醇,二氯新戊基二醇,二溴新戊二醇,新戊基二醇羟基新戊酸酯,环己烷二甲醇,1,4-环己二醇,螺二醇,三环癸烷二甲醇,氢化的双酚A,环氧乙烷-改性的双酚A,环氧丙烷-改性的双酚A,二羟甲基丙酸,二羟甲基丁酸,三羟甲基乙烷,三羟甲基丙烷,甘油,3-甲基戊烷-1,3,5-三醇,三(2-羟乙基)异氰脲酸酯。聚酯-多元醇,聚醚-多元醇,聚碳酸酯-多元醇可用于获得加合物产物。这些醇能单独使用或以两种或多种的混合物使用。
由以上多元醇组分和羧酸的反应获得的聚酯-多元醇可用于制备加合物产物。对于羧酸而言,任何普通的羧酸或它的酸酐都可以使用。这些羧酸的例子包括,例如,马来酸,富马酸,衣康酸,柠康酸,四氢化邻苯二甲酸,hettic酸,氯菌酸,二聚酸,己二酸,琥珀酸,链烯基琥珀酸,癸二酸,壬二酸,2,2,4-三甲基己二酸,1,4-环己烷二羧酸,对苯二甲酸,2-磺酸钠对苯二甲酸,2-磺酸钾对苯二甲酸,间苯二酸;5-磺酸钠间苯二甲酸,5-磺酸钾间苯二甲酸;5-磺酸钠间苯二甲酸的二低级烷基酯如5-磺酸钠间苯二甲酸的二甲基或二乙基酯;邻苯二甲酸,4-磺基邻苯二甲酸,1,10-十亚甲基二酸,己二烯二酸,草酸,丙二酸,戊二酸,偏苯三酸,六氢化邻苯二甲酸,四溴邻苯二甲酸,甲基环己烯三羧酸或1,2,4,5-苯四酸,这些酸的酸酐和这些酸与醇如甲醇和乙醇所形成的酯化合物。也有可能使用由ε-己内酰胺和上述多元醇之间的开环反应所获得的内酯-多元醇。
对于聚醚多元醇,普通聚醚多元醇可用于获得加合物产物。此类聚醚-多元醇的例子是,例如,但不限于,醚二醇类如聚四亚甲基二醇,环氧丙烷-改性的聚四亚甲基二醇,环氧乙烷改性的聚四亚甲基二醇,聚丙二醇,聚乙二醇,和通过使用3以上官能度多元醇作为引发剂通过环醚的开环反应获得的聚醚多元醇。
用于加合物产物中的聚碳酸酯多元醇是通过碳酸酯和各种多元醇的酯基转移反应获得的。碳酸酯的例子是,例如,但不限于,碳酸二苯基酯,碳酸双(氯苯基)酯,碳酸二萘基酯,碳酸苯基甲苯基酯,碳酸苯基氯苯基酯,和碳酸2-甲苯基-4-甲苯基酯;碳酸二芳基-或二烷基酯如碳酸二甲酯和碳酸二乙酯。能够用于以上反应的多元醇的例子包括以上所述的醇,多元醇,聚酯多元醇,和聚醚多元醇。
被分类在乙烯基醚类型中的具有酯连接基的化合物能够通过在一个分子中有至少一个羟基的亚烷基二醇的单乙烯基醚与在一个分子有至少一个羧基的化合物间的酯化反应获得。
在一个分子中具有至少一个羟基的亚烷基二醇的单乙烯基醚的例子与作为以上所述具有脲烷键的化合物的组分所列举的那些化合物相同。
对于在分子中具有至少一个羧基的化合物,有可能使用众所周知的羧酸及其酸酐。在分子有至少一个羧基的化合物的例子包括,例如,但不限于:甲酸,乙酸,丙酸,戊酸,苯甲酸,马来酸,富马酸,衣康酸,柠康酸,四氢化邻苯二甲酸,hettic酸,氯菌酸,二聚酸,己二酸,琥珀酸,链烯基琥珀酸,癸二酸,壬二酸,2,2′,4-三甲基己二酸,1,4-环己烷二羧酸,对苯二甲酸,2-磺酸钠对苯二甲酸,2-磺酸钾对苯二甲酸,间苯二酸,5-磺酸钠间苯二甲酸,5-磺酸钾间苯二甲酸;5-磺酸钠间苯二甲酸的二低级烷基酯如5-磺酸钠间苯二甲酸的二甲基-或二乙基酯,邻苯二甲酸,4-磺基邻苯二甲酸,1,10-十亚甲基二羧酸,己二烯二酸,草酸,丙二酸,戊二酸,偏苯三酸,六氢化邻苯二甲酸,四溴邻苯二甲酸,甲基环己烯三羧酸或1,2,4,5-苯四酸,以及这些化合物的酸酐。另外,羧酸类可由具有两个以上羧基的化合物和各种醇之间的反应获得,它们可用作具有脲烷键的化合物当中的组分,而且它们可用于获得异氰酸酯的加合物产物。
可一起用于活性能量可固化组合物中的乙烯基羧酸酯衍生物包括,例如,醋酸乙烯基酯和肉桂酸乙烯基酯。苯乙烯衍生物包括,例如,苯乙烯和二乙烯基苯乙烯。
可一起用于本发明的活性能量可固化组合物中的不饱和聚酯包括,例如,马来酸酯如马来酸二甲酯和马来酸二乙酯;富马酸酯如富马酸二甲酯和富马酸二乙酯;以及不饱和多羧酸如马来酸和富马酸与多羟基醇的酯化产物。
能够使用一种或多种任何化合物的无限制性混合物,不限于前面所述的化合物和由通式(1)表示的作为可一起用于本发明的活性能量可固化组合物中的可固化化合物的那些。然而,该化合物必须能够与本文所述的马来酰亚胺衍生物共聚合。
本文中短语“水相容性”用来描述可用水部分或完全稀释的、水溶性的和/或能够与本文所述的能量可固化组合物形成水乳液或分散液的那些化合物。然而,对于能量可固化组合物用于配制涂料的情况,优选的是,所述水相容性化合物同时与水和马来酰亚胺相容,为的是避免一种或多种组分的任何相分离或沉淀。尽管不希望受理论的束缚,用于涂料应用的水相容性树脂化合物似乎更合适,如果它同时具有与水相容的官能团和与马来酰亚胺衍生物相容的官能团。
虽然当两种马来酰亚胺一起用于含有马来酰亚胺衍生物的活性能量可固化组合物中时对由通式(1)表示的马来酰亚胺衍生物与另外那些马来酰亚胺衍生物的比率没有特别的限制,但是,优选的是选择除由通式(1)表示的那些以外的马来酰亚胺衍生物的比率等于或低于95wt%,更优选等于或低于90wt%。
虽然当用于本发明的含有马来酰亚胺衍生物的活性能量可固化组合物中时对具有丙烯酰氧基或甲基丙烯酰氧基的化合物与由通式(1)表示的马来酰亚胺衍生物的比率没有限制,但是,优选的是,在使用具有丙烯酰氧基或甲基丙烯酰氧基的化合物时应使得100重量份的具有丙烯酰氧基或甲基丙烯酰氧基的化合物对应5重量份或5重量份以上的由通式(1)表示的马来酰亚胺衍生物,和更优选地,从固化速度考虑,对应于20重量份或20重量份以上的马来酰亚胺衍生物。
当具有乙烯基醚基团的化合物一起用于本发明的含有马来酰亚胺衍生物的活性能量可固化组合物中时,对引入到组合物中的比例没有限制。然而,优选的是使用具有乙烯基醚基团的化合物以使得100重量份的具有乙烯基醚基团的化合物对应5重量份或5重量份以上的由通式(1)表示的马来酰亚胺衍生物,而且从固化速度和固化膜性能考虑,使用与马来酰亚胺基等摩尔量的乙烯基醚基团是更加优选的。
本发明的活性能量可固化组合物具有在200-400nm范围内的固有光谱敏感性,因此有可能在180nm-500nm范围内的紫外线或可见光的辐射下聚合该组合物,甚至不需要使用光引发剂。可以观察到,具有在254nm、308nm、313nm和365nm处的波长的光可有效地固化本发明的活性能量可固化组合物。也有可能利用除紫外线以外的光和通过加热来固化或聚合本发明的活性能量可固化组合物。另外,有可能在空气和/或惰性气体中固化本发明的活性能量可固化组合物。各种能量固化源如热、紫外线、红外线和可见光都可以使用,例如,低压水银灯,高压水银灯,超高压水银灯,金属卤化物灯,化学灯,黑光灯,水银-氙灯,受激准分子灯,短弧灯,氦-镉激光,氩激光,受激准分子激光,和日光。
虽然本发明的活性能量可固化组合物能够在没有光引发剂存在下,利用紫外线或可见光的辐射来固化,但是尽管如此,普通的光引发剂仍可用于聚合反应中。光引发剂可区分为两类;一类是分子内化学键分裂型和另一类是分子内夺氢型。
分子内化学键分裂型光引发剂的例子包括,例如,乙酰苯类如二乙氧基乙酰苯,2-羟基-2-甲基-1-苯基丙烷-1-酮,苄基二甲基缩酮,1-(4-异丙基苯基)-2-羟基-2-甲基丙烷-1-酮,4-(2-羟基乙氧基)苯基-(2-羟基-2-甲基丙基)酮,4-(2-羟基乙氧基)苯基-(2-羟基-2-丙基)酮,1-羟基环己基-苯基酮,2-甲基-2-吗啉子基(4-甲硫基苯基)丙烷-1-酮,和2-苄基-2-二甲基胺基-1-(4-吗啉子基苯基)-丁酮;苯偶姻类如苯偶姻,苯偶姻甲基醚,苯偶姻异丙基醚;酰基膦氧化物如2,4,6-三甲基苯偶姻二苯基膦氧化物;苄基和甲基苯基乙醛酸酯。
分子内夺氢型光引发剂的例子包括,例如,二苯甲酮类如二苯甲酮,4-苯基二苯甲酮o-苯甲酰基苯甲酸甲酯,4,4′-二氯二苯甲酮,羟基二苯甲酮,4-苯甲酰基4′-甲基-二苯基硫醚,丙烯酸-二苯甲酮,3,3′,4,4′-四(叔丁基过氧羰基)二苯甲酮,3,3′-二甲基-4-甲氧基二苯甲酮;噻吨酮如2-异丙基噻吨酮,2,4-二甲基噻吨酮,2,4-二乙基噻吨酮,2,4-二氯噻吨酮;氨基二苯甲酮类如Michler氏酮,4,4′-二乙基氨基二苯甲酮;10-丁基-2-氯吖啶酮,2-乙基蒽醌,9,10-菲醌,和樟脑醌。
优选的是以0.01-10.00wt%的量将光引发剂加入到活性能量可固化组合物中。
虽然本发明的活性能量可固化组合物能够利用紫外线的辐射来固化,但还有可能使用增感剂以实现高效固化。
此类增感剂的例子是,例如,胺类如三乙醇胺,甲基二乙醇胺,三异丙醇胺,4-二甲基氨基苯甲酸甲酯,4-二甲基氨基苯甲酸乙酯,4-二甲基氨基苯甲酸异戊基酯,苯甲酸(2-二甲基胺基)乙酯,4-二甲基氨基苯甲酸(正丁氧基)乙基酯,和4-二甲基氨基苯甲酸2-乙基己基酯。优选的是以0.01-10.00wt%的量将增感剂加入到活性能量可固化组合物中。
如果需要,还可一起使用添加剂,如非反应活性化合物,无机物填料,有机填料,偶联剂,粘合剂,防沫剂,流平剂,增塑剂,抗氧化剂,紫外线吸收剂,阻燃剂,颜料,染料,和油漆。
一起可用于活性能量可固化组合物中的非反应活性化合物的例子包括,例如,但不限于,具有低反应活性或无反应活性的液体或固体低聚物或树脂,如(甲基)丙烯酸烷基酯共聚物,环氧树脂,液体聚丁二烯,液体聚丁二烯衍生物,液体氯丁二烯,液体聚戊二烯,二氯戊二烯衍生物,饱和聚酯低聚物,聚醚低聚物,丙烯酸低聚物,液体聚酰胺,多异氰酸酯低聚物,二甲苯树脂,丙烯酸树脂,酮类树脂,石油树脂,松香树脂,氟化型低聚物,硅氧烷型低聚物,多硫化物低聚物。
无机和有机填料一般用于改进机械性能如强度、缓冲和滑动性质。
可使用任何普通的填料,如果该填料与含水的组合物相容并且不损害树脂的特性包括固化性能的话。可使用的无机填料包括,例如,但不限于,二氧化硅,氧化硅,碳酸钙,硅酸钙,碳酸镁,氧化镁,滑石,高岭土粘土,煅烧粘土,氧化锌,硫酸锌,氢氧化铝,氧化铝,玻璃,云母,硫酸钡,矾土白,沸石,硅石微球,和玻璃微球。有可能通过加成或通过与各种偶联剂如硅烷偶联剂、钛酸酯型偶联剂、铝型偶联剂、锆酸酯型偶联剂等反应,将卤素基团、环氧基团、羟基和硫醇基团引入到这些填料中。
可使用的普通有机填料包括,例如,但不限于,苯并胍胺树脂,硅氧烷树脂,低密度聚乙烯,高密度聚乙烯,聚烯烃树脂,乙烯-丙烯酸酯共聚物,聚苯乙烯,交联聚苯乙烯,聚二乙烯基苯,苯乙烯-二乙烯基苯共聚物,丙烯酸系共聚物,交联丙烯酸树脂,聚甲基丙烯酸甲酯树脂,偏二氯乙烯树脂,氟树脂,尼龙12,尼龙11,尼龙6/66,酚树脂,环氧树脂,聚氨酯树脂,和聚酰亚胺树脂。有可能将卤素基团、环氧基、羟基和硫醇基团引入到这些有机填料中。
能够一起用于本发明的活性能量可固化组合物中的偶联剂的例子包括,例如,但不限于,硅烷偶联剂如γ-缩水甘油氧基丙基三甲氧基硅烷,和γ-氯丙基三甲氧基硅烷;钛酸酯偶联剂如四(2,2-二芳氧基甲基-1-丁基)双(双十三烷基)亚磷酸酯钛酸酯和双(二辛基焦磷酸酯)亚乙基钛酸酯;铝偶联剂如乙酰基烷氧基铝二异丙氧基化物;锆偶联剂如乙酰基丙酮-锆配合物等等。
对于添加剂如粘合剂,防沫剂,流平剂,流动助剂,增塑剂,抗氧化剂,紫外线吸收剂,阻燃剂,颜料,染料,和油漆而言,任何相应的普通添加剂均可以不受限制地一起用于本发明的活性能量可固化组合物中,如果该添加剂与含水的组合物相容并且不损害树脂的性能包括固化性能的话。
为了获得本发明的活性能量可固化组合物,上述各组分可以混合,对混合顺序或混合方法没有限制。
在本发明的活性能量可固化组合物中基本上没有必要使用溶剂。然而,为了稀释本发明的活性能量可固化组合物,有可能使用普通的和一般已知的溶剂,其中包括酮类如甲基乙基酮和甲基异丁基酮;乙酸酯类如乙酸乙酯和乙酸丁酯;芳香烃如苯、甲苯和二甲苯;以及醇类如甲醇、乙醇、异丙醇、丁醇;和水。
本发明的活性能量可固化组合物理想地适合用于表面修饰,粘结剂,塑性材料,模塑材料,层压板,粘合剂,粘接材料和油墨;金属如铝、铁和铜的涂料;塑料如氯乙烯塑料、丙烯酸树脂、聚碳酸酯、聚对苯二甲酸乙二醇酯、丙烯腈-丁二烯-苯乙烯共聚物、聚乙烯和聚丙烯的涂料;陶瓷如玻璃的涂料;其它材料如木材、纸张、印刷纸和纤维的涂料。
本发明的活性能量可固化组合物在光辐射下在没有光引发剂的条件下形成固化膜。因为本发明的活性能量可固化组合物在固化过程中不产生气味和该组合物的固化膜不发生泛黄和气味,而且从固化膜中洗脱的量是相当低的,所以,本发明的组合物理想地适用于油墨领域中,如石印墨、多功能油墨、照相凹版印刷油墨和丝网印刷油墨,和用于直接接触消费者的光泽清漆、纸张涂料、木材涂饰剂、饮料罐涂料、印刷、软包装涂料、印刷纸和层压制品的粘合剂、lavel涂料、印刷油墨或粘合剂、热敏纸、热敏纸的印刷油墨或涂料、食品包装涂料、印刷油墨、粘合剂和粘结剂。
下面的实施例用于说明本发明的特定方面并且不希望限制本发明的范围,也不应该如此解释。在实施例中,所有的份数都是按重量计,除非另有说明。重量份数与体积份数的相互关系如同公斤与升的关系。
在实施例中,能量可固化组合物通过使用厚度7.5微米的#3 Mayer棒被涂敷在不透明的图片上(无涂层的Leneta N2A,购自LenetaCorporation,Mawah,NJ)。通过使用以100-200英尺/分钟(fpm)的输送带速度运动的装有可变光强度的中压水银灯(例如120、200、300瓦/英寸(wpi),购自Fusion Aetek,Rockville,MD)的输送带型装置来提供紫外线辐射能量固化源。在200wpi和100fpm下紫外线照射剂量是228mJ/cm2,该剂量是使用辐射计(UV Power Puck,Power Puck是位于弗吉尼亚州的EIT Incorporated的注册商标)测得的。该剂量正常足以生产出有工业价值的膜。涂层的表面硬度根据经验用手指甲刮表面来测量。通过使用光泽计(Micro-Gloss 60,购自BYK-GardnerIncorporated,MD)在60°下测量固化膜的反射光泽。通过用浸泡在丁酮(MEK)、异丙醇或水中的棉花尖头涂敷棒擦拭表面,直至基底露出为止,来测量固化膜的耐溶剂性能。记录下往返擦洗即沿着表面来回一个冲程的次数。例如,显示出10次往返擦洗耐MEK性能的涂层被认为是工业上可行的。
实施例1
合成实施例
甘氨酸(37.5g)和乙酸(400ml)被混合在一起,然后在搅拌下用2小时滴加马来酸酐(49.0g)和乙酸(300ml)的溶液。反应继续进行1小时并过滤出所形成的沉淀物并从70%甲醇水溶液中重结晶。向该产物(102g)中添加三乙胺(40.4g)和甲苯(500ml),让混合物反应1小时,与此同时在回流下加以搅拌以除去所散发出的水。通过从反应混合物中除去甲苯所获得的残余物用0.1N HCl酸化至PH值为2,用乙酸乙酯(100ml)萃取3次并和用硫酸镁干燥。然后在减压下蒸发出乙酸乙酯,残余物从水中重结晶,据此获得了马来酰亚胺基乙酸(11g)的浅黄色晶体。1H NMR(300MHz,DMSO-d6):7.0ppm(s,2H,-C=C-);4.1ppm(s,2H,-CH2-);IR:3170cm-1(-COOH);1750cm-1,1719cm-1(C=O);831cm-1;696cm-1(-C=C-);元素分析(CHN):计算值C:46.5%;H:3.87%;N:9.03%;实测值C:46.2%;H:4.05%;和N:8.70%。
马来酰亚胺基乙酸(6.8g),聚四亚甲基二醇(10g,Mw为250,商品名PolyTHF 250,可以从日本的BASF Corporatioin获得),对甲苯磺酸(1.2g),2,6-二叔丁基-对-甲苯酚(0.06g),和甲苯(15ml)被添加在一起并在减压下(240托)于80℃下反应4小时。对混合物进行搅拌,并除去在反应过程中所形成的水。反应混合物然后被溶于甲苯(200ml)中和用饱和碳酸氢钠水溶液(100ml)和饱和氯化钠水溶液(100ml)都洗涤3次。在减压下除去甲苯,获得具有以下结构的马来酰亚胺衍生物(16g)。
实施例2
合成实施例
甘氨酸(37.5g)和乙酸(400ml)被混合在一起,然后在搅拌下用2小时滴加马来酸酐(49.0g)和乙酸(300ml)的溶液。反应继续进行1小时并过滤出所形成的沉淀物并从70%甲醇水溶液中重结晶。向该产物(102g)中添加三乙胺(40.4g)和甲苯(500ml),让混合物反应1小时,与此同时在回流下加以搅拌以除去所散发出的水。通过从反应混合物中除去甲苯所获得的残余物用0.1N HCl酸化至PH值为2,用乙酸乙酯(100ml)萃取3次并用硫酸镁干燥。然后在减压下蒸发出乙酸乙酯,残余物从水中重结晶,据此获得了马来酰亚胺基乙酸(11g)的浅黄色晶体。1H NMR(300MHz,DMSO-d6):7.0ppm(s,2H,-C=C-);4.1ppm(s,2H,-CH2-)IR:3170cm-1(-COOH);1750cm-1;1719cm-1(C=O);831cm-1;696cm-1(-C=C-);元素分析(CHN)计算值C:46.5%;H:3.87%;N:9.03%;实测值C:46.2%;H:4.05%;和N:8.70%。
将马来酰亚胺基乙酸(6.8g),被4摩尔环氧乙烷改性的季戊四醇(4.1g,商品名PNT-40Mn:490,Mw:530,购自Nippon EmulsifyingAgent Co.,Ltd.,日本),对-甲苯磺酸(1.2g),2,6-二叔丁基-对-甲苯酚(0.06g)和甲苯(15ml)添加在一起,并在减压(240托)下于80℃下反应4小时。对混合物进行搅拌,并除去在反应过程中所形成的水。反应混合物然后被溶于甲苯(200ml)中并用饱和碳酸氢钠水溶液(100ml)和饱和氯化钠水溶液(100ml)都洗涤3次。在减压下除去甲苯,获得具有以下结构的马来酰亚胺衍生物(18g)。
实施例3
脂族环氧丙烯酸酯树脂(55wt.%,Laromer 8765,购自BASF,Mt.Olive,NJ)与水(8.5wt.%)混合。接着,添加按照实施例1中制得的马来酰亚胺(36wt.%)。将聚醚硅氧烷添加剂(0.5wt.%,Glide440,购自Tego Chemie,VA)加入以产生足够的流动性质。然后评价如以上所述的涂料的固化、耐溶剂性、光泽和表面硬度性能。结果显示于表1中。
实施例4
(对比)
向水(15wt.%)中添加按照实施例1中制得的马来酰亚胺(84.5wt.%)。将聚醚硅氧烷添加剂(0.5wt.%,Glide 440,购自Tego Chemie,VA)加入以产生足够的流动性质。该涂料的能量固化性能无法评价,因为发现水和马来酰亚胺不相容和因此无法得到膜。
实施例5
脂族环氧丙烯酸酯树脂(58wt.%,Laromer 8765,购自BASF,Mt.Olive,NJ)与水(13.6wt.%)混合。接着,添加光引发剂,4-(2-羟基乙氧基)苯基-(2-羟基-2-甲基丙基)酮(3wt.%,Irgacure 2959,可以从Ciba-Geigy,NY获得)。将聚硅氧烷添加剂(0.4wt.%,DC57,购自DowChemical,Midland MI)加入以产生足够的流动性质。最后,添加按照实施例1中制得的马来酰亚胺(25wt.%)。然后评价如以上所述的涂料的固化、耐溶剂性、光泽和表面硬度性能。结果显示于表1中。
实施例6
脂族环氧丙烯酸酯树脂(50wt.%,Laromer 8765,购自BASF,Mt.Olive,NJ)与水(17wt.%)混合。然后,将按照实施例1中制得的马来酰亚胺(17wt.%,MIA250)与异丙醇(15.5wt.%)一起添加。将聚醚硅氧烷添加剂(0.5wt.%,Glide 440,购自Tego Chemie,VA)加入以产生足够的流动性质。组合物以三种不同的剂量照射。然后评价如以上所述的涂料对于每一剂量的固化、耐溶剂性、光泽和表面硬度性能。结果显示于表1中。
实施例7
将水可稀释的脂族脲烷-丙烯酸树脂(25wt.%,Ebecryl 2001,购自UCB Radcure,GA)与水(49.5wt.%)混合。将按照实施例1中制得的马来酰亚胺(25wt%,MIA250)与聚醚硅氧烷添加剂(0.5wt.%,Glide440,购自Tego Chemie,VA)一起添加以产生足够的流动性能。组合物以两种不同的剂量照射。然后评价如以上所述的涂料的固化、耐溶剂性、光泽和表面硬度性能。结果显示于表1中。
实施例8
将高度烷氧基化的三丙烯酸(三羟甲基丙烷)酯树脂(61wt.%,SR9035,购自Sartomer,PA)与水(24wt.%)相混合。添加按照实施例1中制得的马来酰亚胺(14.5wt.%)。将聚醚硅氧烷添加剂(0.5wt.%,Glide440,购自Tego Chemie,VA)加入以产生足够的流动性质。组合物以两种不同的剂量照射。然后评价如以上所述的涂料的固化、耐溶剂性、光泽和表面硬度性能。结果显示于表1中。
实施例9
脂族环氧丙烯酸酯树脂(57wt.%,Laromer 8765,购自BASF,Mt.Olive,NJ)与水(10.5wt.%)混合。然后添加一种乙烯基醚,即己二酸[双(4-乙烯基氧基)丁基]酯(10.5wt.%,VEX 4060,可以购自AlliedSignal,NJ)。然后将按照实施例1中所制得的马来酰亚胺(21.5wt.%)与聚硅氧烷添加剂(0.5wt.%,DC57,可以购自Dow Chemical,Midland,MI)一起添加以产生足够的流动性能。组合物以两种不同的剂量照射。然后评价如以上所述的涂料的固化、耐溶剂性、光泽和表面硬度性能。结果显示于表1中。
实施例10
(对比)
将一种乙烯基醚,即己二酸[双[4-乙烯基氧基)丁基]酯(67wt%,VEX 4060,可以购自Allied Signal,NJ)加入到水(11wt.%)中。然后将按照实施例1中所制得的马来酰亚胺(21.5wt%)与聚醚硅氧烷添加剂(0.5wt%,DC57,可以购自Dow Chemical,Midland,MI)一起添加以产生足够的流动性能。涂料的能量固化性能无法评价,因为发现水和马来酰亚胺不相容和因此无法形成膜。
实施例11
脂族环氧丙烯酸酯树脂(72 wt.%,Laromer 8765,购自BASF,Mt.Olive,NJ)与水(16wt.%)混合。然后添加按照实施例2中制得的马来酰亚胺(11.2wt.%,MIA-PE4EO)。将聚醚硅氧烷添加剂(0.8wt.%,Glide440,购自Tego Chemie,VA)加入以产生足够的流动性质。然后评价如以上所述的涂料的固化、耐溶剂性、光泽和表面硬度性能。结果显示于表1中。
实施例12
(对比)
向水(15wt.%)中添加按照实施例2中制得的马来酰亚胺(84.5wt.%,MIA-PE4EO)。将聚醚硅氧烷添加剂(0.5wt%,Glide 440,购自Tego Chemie,VA)加入以产生足够的流动性质。涂料的能量固化性能无法评价,因为发现水和马来酰亚胺不相容和因此无法得到膜。
表1
实施例 | 固化速率(mJ/cm3) | 表面硬度 | 60°光泽(%) | 溶剂擦洗次数(MEK) | 溶剂擦洗次数(水) |
3 | 228 | 优异 | 85-90 | 65 | >200 |
5 | 228 | 优异 | 92 | 40-44 | >200 |
6 | 125 | 非常良好 | 85-88 | 8 | 50 |
6 | 209 | 非常良好 | 88-90 | 12-15 | 70 |
6 | 254 | 优异 | 88-90 | 38 | >200 |
7 | 228 | 良好 | 80-82 | 45 | N.A. |
7 | 607 | 非常良好 | 80-82 | 75 | N.A. |
8 | 204 | 一般 | 65-70 | 3 | 8 |
8 | 305 | 良好 | 65-70 | 5 | 19 |
9 | 228 | 非常良好 | 86-87 | 9 | 31 |
9 | 456 | 优异 | 87-88 | 31 | 66 |
11 | 228 | 一般 | 86 | 26 | 80 |
表1中数据显示了本发明的水相容性能量可固化组合物的几个特征。为固化本发明组合物所需要的剂量与用于固化普通能量可固化材料的剂量类似。固化膜的表面硬度和光泽与使用光引发剂的商品涂料具有可比性。固化组合物的耐溶剂擦洗性能与使用含有商购光引发剂和树脂的类似组合物所获得的结果十分相近。这可通过实施例3来举证,其中228mJ/cm2的固化速率表示100fpm的输送机速度和200wpi灯强度,两者表示工业上为固化该组合物所输送的实际能量的多少。实施例3加7表现出了高于80的光泽值,它是高商品级光泽的表示。实施例3描述了用MEK时为65次和用水时大于200次的耐溶剂擦洗次数。这些值典型地高于在类似条件下固化的普通商购涂料所显示的那些值。实施例6揭示了,通过将本发明的能量可固化组合物的固化剂量翻倍,从125提高至254mJ/cm2,则能够提高其膜性能,如表面硬度、光泽和交联密度,该交联密度可通过耐溶剂性能来测量并可通过MEK溶剂擦洗次数从8次增加到38次来说明。实施例9显示了溶剂擦洗次数的类似增加,从耐9次增到31次MEK擦洗和从耐31次增到66次水擦洗。虽然较高的固化速率是需要的,但是它仍然在工业上的固化范围内。
对本发明已经详细地进行了描述,其中包括它的优选实施方案。然而,应该认识到的是,本技术领域中的那些技术人员能够对属于权利要求中所列的本发明范围和精神内的实施方案作许多变化或改进。
Claims (19)
1.一种活性的水相容性能量可固化单相组合物,它包括水相容性非乳化的非分散性的化合物、水和具有下式的马来酰亚胺衍生物:
其中n和m各自独立地表示1-5的整数,m和n的总和是6或更低;
R11和R12各自独立地表示选自亚烷基、脂环族基团、芳基亚烷基和环烷基亚烷基的连接基团;
G1和G2各自表示选自-COO-和-OCO-的酯连接基;和R2表示选自(聚)醚或(聚)酯连接链的平均分子量为100-100,000的连接链,其中至少一个基团由通过选自醚或酯连接基的至少一个连接基连接的选自直链或支链C2-C24亚烷基、具有羟基的C2-C24亚烷基、C3-C24脂环族基团、C6-C24芳基、C6-C24芳基-C2-C24亚烷基和C3-C24环烷基-C2-C24亚烷基的基团组成;
所述水相容性非乳化的非分散性的化合物选自:丙烯酸酯树脂;甲基丙烯酸酯树脂;丙烯酸分散体;脲烷树脂;乙烯基醇;乙烯醇共聚物;多糖;聚蔗糖;和葡萄糖。
2.权利要求1的能量可固化单相组合物,其中R2是平均分子量为100-100,000并由含有选自C2-C24直链或支链亚烷基、具有羟基的C2-C24亚烷基和C6-C24芳基的至少一个基团的重复单元组成的(聚)醚连接链。
3.权利要求2的能量可固化单相组合物,其中R2是由含有选自C2-C24直链或支链亚烷基或具有羟基的C2-C24亚烷基的至少一个基团的重复单元组成。
4.权利要求1的能量可固化单相组合物,其中R2是平均分子量为100-100,000并由含有选自C2-C24直链或支链亚烷基、具有羟基的C2-C24亚烷基和C6-C24芳基的至少一个基团的重复单元组成的(聚)酯连接链。
5.权利要求3的能量可固化单相组合物,其中R2是由含有选自C2-C24直链或支链亚烷基或具有羟基的C2-C24亚烷基的至少一个基团的重复单元组成。
6.权利要求1的能量可固化单相组合物,其中所述水相容性化合物是选自丙烯酸酯和脲烷树脂的树脂。
7.权利要求6的能量可固化单相组合物,其中所述丙烯酸酯树脂是脂肪族环氧丙烯酸酯。
8.权利要求6的能量可固化单相组合物,其中所述脲烷树脂是脂肪族脲烷丙烯酸酯。
9.权利要求1的能量可固化单相组合物,进一步包括可与所述马来酰亚胺衍生物和水相容性化合物共聚合的化合物。
10.权利要求9的能量可固化单相组合物,其中所述可共聚合的化合物包括至少一种从具有至少一个选自丙烯酰氧基和甲基丙烯酰氧基的基团的化合物及具有乙烯基醚基团的化合物中选择的化合物。
11.权利要求10的能量可固化单相组合物,其中所述具有至少一个选自丙烯酰氧基和甲基丙烯酰氧基的基团的化合物包括选自(聚)酯(甲基)丙烯酸酯、脲烷(甲基)丙烯酸酯、环氧树脂(甲基)丙烯酸酯、(聚)醚(甲基)丙烯酸酯的至少一种化合物,选自(甲基)丙烯酸烷基酯、(甲基)丙烯酸亚烷基酯、具有芳族基团的(甲基)丙烯酸酯和具有脂环族基团的(甲基)丙烯酸酯的至少一种化合物。
12.权利要求10的能量可固化单相组合物,其中所述具有乙烯基醚基团的化合物包括选自以下化合物中的至少一种:具有被至少一个选自氢原子、卤素原子、羟基和氨基的基团所取代的端基的烷基乙烯基醚;具有被至少一个选自氢原子、卤素原子、羟基和氨基的基团所取代的端基的环烷基乙烯基醚;以及选自单乙烯基醚、二乙烯基醚和多乙烯基醚中的至少一种乙烯基醚,其中经由选自醚连接基、脲烷连接基和酯连接基的至少一个连接基,乙烯基醚基团与亚烷基相连和乙烯基醚基团与有和没有取代基的从烷基、环烷基和芳族基团中选择的至少一种基团相连。
13.权利要求1的能量可固化单相组合物,其中R2选自平均分子量大于200的(聚)醚或(聚)酯连接链。
14.包括权利要求1的活性、水相容性、能量可固化的单相组合物的油墨或涂料。
15.将权利要求1的活性、水相容性、能量可固化的单相组合物固化的方法,它包括对所述的组合物进行辐射。
16.权利要求15的方法,其中在辐射之前没有必要将能量可固化的单相组合物干燥。
17.根据权利要求15的方法,其中在辐射之后没有必要将能量可固化的单相组合物干燥。
18.权利要求15的方法,其中马来酰亚胺衍生物中的R2是分子量大于200的(聚)醚或(聚)酯连接链。
19.权利要求15的方法,进一步包括添加可与所述马来酰亚胺衍生物和水相容性化合物共聚合的化合物。
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JP7967898A JP3599160B2 (ja) | 1997-05-16 | 1998-03-26 | マレイミド誘導体を含有する活性エネルギー線硬化性組成物及び該活性エネルギー線硬化性組成物の硬化方法 |
JP07967998A JP3601654B2 (ja) | 1997-05-16 | 1998-03-26 | マレイミド誘導体を含有する活性エネルギー線硬化性組成物及び該硬化性組成物の硬化方法 |
JP9321598A JPH11292874A (ja) | 1998-04-06 | 1998-04-06 | マレイミド誘導体、マレイミド誘導体を含有する活性エネルギー線硬化性組成物及び該活性エネルギー線硬化性組成物の硬化方法 |
JP10767198A JPH11302278A (ja) | 1998-04-17 | 1998-04-17 | マレイミド誘導体、該誘導体を含有する活性エネルギー線硬化性組成物及び該硬化性組成物の硬化方法 |
PCT/US1998/024300 WO1999048928A1 (en) | 1998-03-26 | 1998-11-14 | Water compatible energy curable compositions containing maleimide derivatives |
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EP (1) | EP1073685B1 (zh) |
JP (1) | JP4361685B2 (zh) |
CN (1) | CN1163518C (zh) |
AU (1) | AU776635B2 (zh) |
BR (1) | BR9815774A (zh) |
CA (1) | CA2326177C (zh) |
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CN109661412A (zh) * | 2016-08-08 | 2019-04-19 | Prc-迪索托国际公司 | 可光化辐射固化的含氨基甲酸酯/脲的航天涂料和密封剂 |
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EP1073685A1 (en) | 2001-02-07 |
WO1999048928A1 (en) | 1999-09-30 |
EP1073685B1 (en) | 2006-08-30 |
MXPA01004775A (es) | 2005-06-13 |
CA2326177C (en) | 2010-04-06 |
US6706777B1 (en) | 2004-03-16 |
DE69835773T2 (de) | 2007-09-13 |
US20040110858A1 (en) | 2004-06-10 |
BR9815774A (pt) | 2000-11-14 |
AU776635B2 (en) | 2004-09-16 |
US7026370B2 (en) | 2006-04-11 |
JP4361685B2 (ja) | 2009-11-11 |
CA2326177A1 (en) | 1999-09-30 |
AU1586499A (en) | 1999-10-18 |
CN1291201A (zh) | 2001-04-11 |
JP2003508546A (ja) | 2003-03-04 |
DE69835773D1 (de) | 2006-10-12 |
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