CN1333027C - 可通过高能辐射固化的丙烯酰氧基官能的硅氧烷组合物 - Google Patents
可通过高能辐射固化的丙烯酰氧基官能的硅氧烷组合物 Download PDFInfo
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- CN1333027C CN1333027C CNB200480005629XA CN200480005629A CN1333027C CN 1333027 C CN1333027 C CN 1333027C CN B200480005629X A CNB200480005629X A CN B200480005629XA CN 200480005629 A CN200480005629 A CN 200480005629A CN 1333027 C CN1333027 C CN 1333027C
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Abstract
一种可通过高能辐射固化的丙烯酰氧基官能的硅氧烷组合物,其特征在于组合物优良的储存稳定性,和由前述组合物生产的硬质固化涂布膜的改进的抗划伤性、透明度、防水性和粘合性。该组合物包括(A)至少一类多官能团丙烯酸酯;氨基改性的有机聚硅氧烷(B),或者至少一类多官能团丙烯酸酯和氨基改性的有机聚硅氧烷之间的迈克尔加成反应的产物(F);(C)具有脂族不饱和键的有机烷氧基硅烷;(D)胶态二氧化硅;和(E)含醇的有机溶剂。
Description
[0001]本发明涉及可通过高能辐射固化的丙烯酰氧基官能的硅氧烷组合物,其特征在于优良的储存稳定性且适于形成证明具有改进的抗划伤性、透明度、防水性和粘合性的固化涂布膜。
[0002]当暴露于紫外线、电子束、γ射线或类似的高能辐射束下时固化的已知的可辐射固化的涂布剂可包括由多官能的丙烯酸酯单体、氨基官能的烷氧基硅烷和胶态二氧化硅组成的组合物(参见EP687713、EP666290、EP437327),或者二丙烯酸酯和氨基改性的聚硅氧烷之间的迈克尔加成反应的产物(参见USP4603086和日本专利申请公开公布No.Hei 11-12361)。
[0003]然而,含有氨基官能的烷氧基硅烷和胶态二氧化硅的最先提及的涂布剂容易胶凝且具有较低的储存稳定性,而第二提及的二丙烯酸酯和氨基改性的聚硅氧烷之间的加成反应的产物当形成为固化膜时,具有低的抗划伤性。
[0004]本发明的目的是提供可通过高能辐射固化的丙烯酰氧基官能的硅氧烷组合物,其特征在于优良的储存稳定性,当固化成涂布膜时改进的抗划伤性、透明度、防水性,以及改进的粘合性。
[0005]本发明涉及可通过高能辐射固化的丙烯酰氧基官能的硅氧烷组合物,它包括:
(A)至少一类多官能的丙烯酸酯;
(B)氨基改性的有机聚硅氧烷,其中组分(B)内氨基的摩尔量小于组分(A)内丙烯酸酯官能团的摩尔量;
(C)具有脂族不饱和键的有机烷氧基硅烷;
(D)胶态二氧化硅;和
(E)含醇的有机溶剂。
[0006]此外,本发明涉及可通过高能辐射固化的丙烯酰氧基官能的硅氧烷组合物,它包括:
(A)至少一类多官能的丙烯酸酯;
(F)在(A)至少一类多官能的丙烯酸酯和(B)氨基改性的有机聚硅氧烷之间的迈克尔加成反应的产物;
(C)具有脂族不饱和键的有机烷氧基硅烷;
(D)胶态二氧化硅;和
(E)含醇的有机溶剂。
[0007]组分(A)是在辐射的作用下赋予本发明组合物可固化性的一种组分。该组分包括二或更高官能度的丙烯酸酯。下述是适于用作组分(A)的化合物的具体实例:1,6-己二醇二丙烯酸酯、1,4-丁二醇二丙烯酸酯、乙二醇二丙烯酸酯、二甘醇二丙烯酸酯、四甘醇二丙烯酸酯、三丙二醇二丙烯酸酯、新戊二醇二丙烯酸酯、1,4-丁二醇二甲基丙烯酸酯、聚(丁二醇)二丙烯酸酯、四甘醇二甲基丙烯酸酯、1,3-丁二醇二丙烯酸酯、三甘醇二丙烯酸酯、三异丙二醇二丙烯酸酯、聚乙二醇二丙烯酸酯、双酚A二甲基丙烯酸酯,或类似的双官能的丙烯酸酯单体;三羟甲基丙烷三丙烯酸酯、三羟甲基丙烷三甲基丙烯酸酯、季戊四醇单羟基三丙烯酸酯、三羟甲基丙烷三乙氧基三丙烯酸酯,或类似的三官能的丙烯酸酯单体;季戊四醇四丙烯酸酯、双三羟甲基丙烷四丙烯酸酯,或类似的四官能的丙烯酸酯单体;二季戊四醇六丙烯酸酯、二季戊四醇(单羟基)五丙烯酸酯,或类似的五或更高官能度的丙烯酸酯单体。也可使用多官能的丙烯酸酯的低聚物和可用下述具体实例作为代表:双酚A环氧二丙烯酸酯、六官能的芳族聚氨酯丙烯酸酯[商品名:Ebecryl 220/UCB Chemicals Corp.]、脂族聚氨酯二丙烯酸酯[商品名:Ebecryl 230/UCB Chemicals Corp.],和四官能的聚酯丙烯酸酯[商品名:Ebecryl 80/UCB Chemicals Corp.]。可单独或结合两种或多种使用前述多官能丙烯酸酯。以上最优选的是五或更高官能度的丙烯酸酯。应当以大于组分(A)的30wt%,优选大于50wt%,和甚至更优选大于80wt%的用量使用这些。
[0008]组分(B)是赋予由本发明的组合物获得的固化涂布膜诸如防水和润滑性之类性能的组分。该组分是有机聚硅氧烷流体,其在分子端基上和部分地在分子侧链上含有氨基官能的有机基团。前述氨基官能的有机基团可用下述为代表:2-氨基乙基、3-氨基丙基、3-(2-氨基乙基)氨基丙基和6-氨基己基。也可使用除了氨基官能的有机基团以外的与硅键合的基团,和可用下述为代表:甲基、乙基、丙基或类似的烷基;苯基或类似的芳基;甲氧基、乙氧基、丙氧基或类似的烷氧基;和羟基。上述最优选的是甲基。组分(B)的有机聚硅氧烷可具有直链、或部分支化的直链结构。该有机聚硅氧烷的聚合度应当在2-1000范围内,优选在2-500范围内,和甚至更优选在2-300范围内。组分(B)的实例可包括有机聚硅氧烷,其含有伯胺基且用以下给出的化学式为代表。在这些化学式中,Me表示甲基。
NH2C3H6·Me2SiO(Me2SiO)10SiMe2·C3H6NH2
[0009]建议组分(B)的用量使得提供组分(B)中的全部胺基的摩尔量小于组分(A)中的丙烯酸酯官能团的摩尔量。优选组分(B)的重量小于组分(A)重量的1/5。
[0010]组分(F)是如上所述的组分(A)中的丙烯酸酯官能团和同样如上所述的组分(B)中的氨基之间的反应的产物。
[0011]组分(C)是具有脂族不饱和键的有机烷氧基硅烷。当组分(D)的表面用组分(C)处理时,它改进组分(D)的胶态二氧化硅和组分(A)或组分(B)之间的亲和力并赋予组合物改进的储存稳定性。在固化过程中,它与组分(A)反应,并因此增加固化产物的交联度。在该组分中所使用的具有脂族不饱和键的基团可例举3-(甲基丙烯酰氧基)丙基、3-(丙烯酰氧基)丙基或类似的含丙烯酰基的有机基团;乙烯基、烯丙基、或类似的链烯基。烷氧基可用下述为代表:甲氧基、乙氧基、丙氧基和丁氧基。前述组分(C)可例举下述化合物:3-(甲基丙烯酰氧基)丙基三甲氧基硅烷、3-(甲基丙烯酰氧基)丙基三乙氧基硅烷、3-(甲基丙烯酰氧基)丙基甲基二甲氧基硅烷、3-(丙烯酰氧基)丙基三甲氧基硅烷、乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、甲基乙烯基二甲氧基硅烷和烯丙基三乙氧基硅烷。
[0012]组分(D)是胶态二氧化硅。组分(D)用于增加由本发明的组合物固化的涂布膜的硬度和抗划伤性。组分(D)可包括可在水、醇或有机溶剂中分散的胶态二氧化硅。建议胶态二氧化硅的平均粒度范围为几纳米到几十纳米。
[0013]组分(E)是含醇的有机溶剂。下述是组分(E)的醇的实例:甲醇、乙醇、异丙醇、丁醇、异丁醇、乙二醇、二甘醇、三甘醇、乙二醇单甲醚、二甘醇单甲醚和三甘醇单甲醚。以下是除了醇以外可使用的有机溶剂:丙酮、甲乙酮、甲基异丁基酮或类似的酮;甲苯、二甲苯或类似的芳烃;己烷、辛烷、庚烷或类似的脂族烃;氯仿、二氯甲烷、三氯乙烯、四氯化碳或类似的含有机氯的溶剂;乙酸乙酯、乙酸丁酯、乙酸异丁酯或类似的脂肪酸酯。组分(E)可含有单独的醇或者醇与另一类溶剂的混合物。该混合物可含有醇和两类或更多不同类的溶剂。可以以溶剂总重量的10-90wt%,优选30-70wt%的用量使用醇。
[0014]除了组分(B)以外,对每一组分的含量没有特别限制,但建议对于每100重量份组分(A)来说,组分(B)和组分(C)各自的使用量为1-30重量份,优选1-20重量份。对于每100重量份组分(A)来说,组分(D)的使用量应当为1-100重量份,优选1-80重量份。对于每100重量份组分(A)来说,组分(E)的使用量应当为10-1000重量份,优选10-500重量份。对于每100重量份组分(A)来说,组分(F)的使用量应当为1-100重量份,优选1-50重量份。
[0015]任选地,组合物也可包括水(组分(G))以供组分(C)的水解。对于每100重量份组分(C)来说,它的添加量可以是1-50重量份,优选5-30重量份。亦即,组分(C)与在组分(D)的胶态二氧化硅的表面上的硅烷醇基相互作用并通过组分(G)水解。因此,组分(G)的用量可小于水解全部组分(C)所要求的用量。
[0016]在通过紫外线固化的情况下,本发明的丙烯酰氧基官能的硅氧烷组合物可含有至少一类光聚合引发剂(H)。它可包括例如2-甲基-(4-(甲硫基)苯基)-2-吗啉基-1-丙烷(日本Ciba-Geigy的产品,注册商品名:IRGACURE907)和1-羟基环己基苯基酮(日本Ciba-Geigy的产品,商品名:IRGACURE184)。二苯酮、乙酰苯、苯偶姻或各种苯偶姻衍生物和其它合适的已知光聚合引发剂可用于同一目的。光聚合引发剂可单独或以两种或多种的混合物形式使用。对本发明组合物内的组分(H)的含量没有特别限制,但一般来说对于每100重量份组分(A)来说,应当以1-30重量份,优选1-20重量份的用量范围添加它。
[0017]在与本发明目的不相冲突的范围内,本发明的组合物可含有各种添加剂,如四甲氧基硅烷、四乙氧基硅烷、四(异丙氧基)硅烷或类似的四烷氧基硅烷;甲基三甲氧基硅烷、甲基三乙氧基硅烷、甲基三(异丙氧基)硅烷、乙基三甲氧基硅烷、乙基三乙氧基硅烷、乙基三(异丙氧基)硅烷或类似的烷基烷氧基硅烷。
[0018]视需要,本发明的组合物也可含有增稠剂,紫外线吸收剂,各种颜料、染料或类似的着色剂,铝糊剂,滑石,玻璃料,金属粉末等,丁基化羟基甲苯(BHT)、苯并噻嗪(PTZ)或类似的自聚合的丙烯酸酯类抑制剂或其它添加剂。
[0019]对适于制备本发明组合物的方法没有特别限制,和通常仅仅通过搅拌均匀混合各组分。在此情况下,首先建议引起组分(A)和(B)之间的反应,然后添加其它组分。由于组分(B)中氨基的摩尔量小于组分(A)中丙烯酸酯官能团的摩尔量,因此在组分(A)和组分(B)之间的反应完全之后,紧跟着由未反应的部分组分(A)和组分(F)制备混合物,所述组分(F)是组分(A)和(B)之间的迈克尔加成反应的产物。例如,可通过在从室温到溶剂回流温度的温度范围内,混合前述组分1分钟-20小时的时间段,引起在组分(E)内组分(A)和(B)之间的反应,然后添加组分(C)和组分(D),以及视需要的组分(G),并在从室温到溶剂回流温度的温度范围内继续混合另外1分钟-20小时的时间段,从而制备本发明的组合物。或者可通过在从室温到溶剂回流温度的温度范围内,混合前述组分1分钟-20小时的时间段,引起在组分(E)内组分(A)和(B)之间的反应,结合该产物与通过混合组分(G)和组分(C)与(D)的混合物而获得的混合物,或者结合该产物与组分(C)、(D)和(G)的混合物,然后在从室温到溶剂回流温度的温度范围内混合所得混合物1分钟-20小时的时间段,从而制备该组合物。可在冷却之后添加并混合组分(H)。
[0020]本发明的组合物可被施加在各种基底上,干燥,然后通过暴露于辐射能下非常短的时间段固化。辐射能可包括紫外辐射、电子束、γ射线或类似物。在紫外射线的情况下,可在极端短的暴露时间过程中形成固化的薄的涂布膜。建议射线量不小于2mJ/cm2,优选在10-2000mJ/cm2范围内。若在使用电子束或γ射线的情况下进行固化,则可不需要组分(H)。尽管本发明的组合物可在室温下干燥,但可通过加热加速干燥过程。
[0021]对适于施加本发明组合物的基底没有特别限制。例如,基底可由例如下述材料制备:聚乙烯、聚丙烯或类似的聚烯烃类树脂;聚对苯二甲酸乙二酯、聚间苯二甲酸乙二酯、聚2,6-萘二甲酸乙二酯、聚对苯二甲酸丁二酯、及其共聚物或类似的聚酯类树脂;聚甲醛或类似的聚酰胺类树脂;聚苯乙烯、聚(甲基)丙烯酸酯、聚丙烯腈、聚乙酸乙烯酯、聚碳酸酯、赛璐玢、聚酰亚胺、聚醚酰亚胺、聚苯砜、聚砜、聚醚酮、离聚物树脂、氟树脂或类似的热塑性树脂;三聚氰胺树脂、聚氨酯树脂、环氧树脂、酚树脂、不饱和聚酯树脂、醇酸树脂、脲树脂、有机硅树脂或类似的热固性树脂。对基底的形式不存在特别限制,和后者可包括膜、片材、瓶子、实心体或类似形状。最优选热塑性膜。对基底的厚度没有特别限制,但在膜或片材的情况下,优选范围为5-100微米。
[0022]可通过任何合适的方法,如流涂、浸涂、旋涂、喷涂、幕涂、照相凹板涂布和迈耶尔绕线棒涂布,以薄层的形式施加本发明的组合物到基底上。在施加组合物之前,可对基底的表面进行已知的活化处理如电晕放电处理或使用聚氨酯树脂的锚定处理。当要求提供抗划伤性时,该层的厚度优选在0.5-25微米范围内,更优选1-20微米。在涂布之后紧跟着干燥该薄层并固化。
[0023]当由前述组分(A)-(E),和视需要添加组分(G)和(H),制备通过高能辐射可固化的本发明的丙烯酰氧基官能的硅氧烷组合物时,可提供组合物优良的储存稳定性和由前述组合物生产的硬质固化涂布膜改进的抗划伤性、透明度、防水性和粘合性。
[0024]现参考实践实施例描述本发明。在这些实施例中,所有份是重量份,和Me表示甲基。各种粘度相应于在25℃下的粘度。使用由Kyowa Kaimen Kagaku Co.,Ltd.制备的CA-Z型号的自动接触角计量仪,测量薄的固化层与水的接触角。
[0025]实践实施例1:用52.3g甲苯、21g异丙醇(下称IPA)和23.9g二季戊四醇六丙烯酸酯(60wt%)和二季戊四醇(单羟基)五丙烯酸酯(40wt%)的混合物(丙烯酸酯官能团的含量:0.24mol)填充烧瓶,并搅拌各组分。之后添加1.49g以下给出的平均分子式的氨基改性的二甲基聚硅氧烷流体(氨基含量:0.001mol),和在50℃下加热该混合物并搅拌1小时。
结果产生反应混合物。
[0026]按序结合该产物与3.74g 3-甲基丙烯酰氧基丙基三甲氧基硅烷、44.9g胶态二氧化硅的IPA分散液(浓度:30wt%;胶态二氧化硅颗粒的平均粒度:13nm)、0.46g水,并搅拌各组分1小时。在冷却混合物之后,添加2.25g光聚合引发剂(日本Ciba-Geigy的产品,注册商品名:IRGACURE184)和4.5mg吩噻嗪。所得产物包括丙烯酰氧基官能的硅氧烷组合物A。该组合物的熔体粘度为3mm2/s和在储存6个月之后几乎保持不变。因此,可得出结论,组合物A具有良好的储存稳定性。
[0027]采用绕线棒刮涂器,将所得组合物A施加到188微米厚的PET膜上,并在120℃下干燥涂层2分钟。然后通过暴露于强度为350mJ/cm2的紫外线下固化该涂层。这产生用固化组合物A的2微米厚的涂布层涂布的PET膜。薄的固化涂层具有98°的水接触角,和铅笔硬度为3H。没有观察到油的渗出。
[0028]在室温下保存所得涂布的PET膜1月之后,将赛璐玢胶带粘合到其表面上,以进行涂层的剥离试验(剥离速度:100mm/min,角度180°)。涂层不可能被剥离掉且保持坚固地粘合到PET膜上。
[0029]此外,当用钢棉刮擦薄膜层的表面时,没有划伤。
[0030]使用UV-可见光分光光度计(获自Shimadzu Corp.的UV-可见光记录分光光度计,UV-265FW),测量所得PET膜的透光率(550nm)。透光率甚至高于未处理的PET膜。换句话说,若未处理的膜的透光率假设为100%,则在涂布膜内,此透光率提高到104%。在Taber磨损测试仪上的摩擦试验(500g的摩擦负载和100转的磨轮)没有改变涂布膜的透光特征,所述涂布膜在反复测量之后保持在104%的相同水平下。
[0031]实践实施例2:用52.3g甲苯、21gIPA和23.9g二季戊四醇六丙烯酸酯(60wt%)和二季戊四醇(单羟基)五丙烯酸酯(40wt%)的混合物(丙烯酸酯官能团的含量:0.24mol)填充烧瓶,并搅拌各组分。之后添加1.5g以下给出的平均分子式的氨基改性的二甲基聚硅氧烷流体(氨基含量:0.002mol),和在50℃下加热该混合物并搅拌1小时。
NH2C3H6-Me2SiO(Me2SiO)9SiMe2-C3H6NH2
结果产生反应混合物。
[0032]按序结合该产物与3.7g 3-甲基丙烯酰氧基丙基三甲氧基硅烷、45g胶态二氧化硅的IPA分散液(浓度:30wt%;胶态二氧化硅颗粒的平均粒度:13nm)、0.46g水,并搅拌各组分1小时。在冷却混合物之后,添加2.25g光聚合引发剂(日本Ciba-Geigy的产品,注册商品名:IRGACURE184)和4.5mg吩噻嗪。所得产物包括丙烯酰氧基官能的硅氧烷组合物B。
[0033]采用绕线棒刮涂器,将所得组合物B施加到188微米厚的PET膜上,并在120℃下干燥涂层2分钟。然后通过暴露于强度为350mJ/cm2的紫外线下固化该涂层。这产生用固化组合物B的2微米厚的涂布层涂布的PET膜。
[0034]薄的固化涂层具有100°的水接触角,和铅笔硬度为3H。
[0035]在室温下保存所得涂布的PET膜1月之后,通过与实践实施例1中所述相同的方法,对该涂层进行剥离试验。涂层不可能被剥离掉且保持坚固地粘合到PET膜上。
[0036]此外,当用钢棉刮擦薄膜层的表面时,没有划伤。通过与实践实施例1中所述相同的方法,测量所得PET膜的透光率(550nm)。透光率为105%且与未处理的PET膜相比得到改进。
[0037]使用便携式摩擦测试仪(Shinto Kagaku Co.,Ltd.的产品(Tribogear-Muse Type 941)),测量在固化的涂布膜表面上的静态摩擦系数,和等于0.17μs,与未处理膜表面上的静态摩擦系数(0.19μs)相比,这具有改进。
[0038]实践实施例3:用21g甲苯、52gIPA和24g二季戊四醇六丙烯酸酯(60wt%)和二季戊四醇(单羟基)五丙烯酸酯(40wt%)的混合物(丙烯酸酯官能团的含量:0.24mol)填充烧瓶,并搅拌各组分。之后添加3g以下给出的平均分子式的氨基改性的二甲基聚硅氧烷流体(氨基含量:0.001mol),和在50℃下加热该混合物并搅拌1小时。
NH2C3H6-Me2SiO(Me2SiO)50SiMe2-C3H6NH2
结果产生反应混合物。
[0039]按序结合该产物与3.7g 3-甲基丙烯酰氧基丙基三甲氧基硅烷、45g胶态二氧化硅的IPA分散液(浓度:30wt%;胶态二氧化硅颗粒的平均粒度:13nm)、0.46g水,并搅拌各组分1小时。在冷却混合物之后,添加2.25g光聚合引发剂(日本Ciba-Geigy的产品,注册商品名:IRGACURE184)和4.5mg吩噻嗪。所得产物包括丙烯酰氧基官能的硅氧烷组合物C。
[0040]采用绕线棒刮涂器,将所得组合物C施加到188微米厚的PET膜上,并在120℃下干燥涂层2分钟。然后通过暴露于强度为350mJ/cm2的紫外线下固化该涂层。这产生用固化组合物C的2微米厚的涂布层涂布的PET膜。
[0041]薄的固化涂层具有99°的水接触角,和铅笔硬度为3H。
在室温下保存所得涂布的PET膜1月之后,通过与实践实施例1中所述相同的方法,对该涂层进行剥离试验。涂层不可能被剥离掉且保持坚固地粘合到PET膜上。此外,当用钢棉刮擦薄膜层的表面时,没有划伤。
[0042]通过以与实践实施例1中相同的方法,测量所得PET膜的透光率(550nm)。透光率为103%且与未处理的PET膜相比得到改进。
[0043]通过以与实践实施例2中所述相同的方法,测量在固化的涂布膜表面上的静态摩擦系数,和等于0.11μs,与未处理膜表面上的静态摩擦系数(0.19μs)相比,这具有改进。
[0044]实践实施例4:用52.3g甲苯、21gIPA和23.9g二季戊四醇六丙烯酸酯(60wt%)和二季戊四醇(单羟基)五丙烯酸酯(40wt%)的混合物(丙烯酸酯官能团的含量:0.24mol)填充烧瓶,并搅拌各组分。之后添加1.49g以下给出的平均分子式的氨基改性的二甲基聚硅氧烷流体(氨基含量:0.001mol),和在50℃下加热该混合物并搅拌1小时。
结果产生反应混合物。
[0045]按序结合该产物与3.74g 3-甲基丙烯酰氧基丙基三甲氧基硅烷、44.9g胶态二氧化硅的IPA分散液(浓度:30wt%;胶态二氧化硅颗粒的平均粒度:13nm),并搅拌各组分1小时。在冷却混合物之后,添加2.25g光聚合引发剂(日本Ciba-Geigy的产品,注册商品名:IRGACURE184)和4.5mg吩噻嗪。所得产物包括丙烯酰氧基官能的硅氧烷组合物D。
[0046]采用绕线棒刮涂器,将所得组合物D施加到188微米厚的PET膜上,并在120℃下干燥涂层2分钟。然后通过暴露于强度为350mJ/cm2的紫外线下固化该涂层。这产生用固化组合物D的2微米厚的涂布层涂布的PET膜。
[0047]薄的固化涂层具有97°的水接触角,和铅笔硬度为3H。没有观察到油的渗出。此外,当用钢棉刮擦薄膜层的表面时,没有划伤。
[0048]对比例1:通过以与实践实施例1相同的方法制备丙烯酰氧基官能的硅氧烷组合物,所不同的是不添加3.74g 3-甲基丙烯酰氧基丙基三甲氧基硅烷。所得组合物具有白色浊度,和在储存1个月之后出现白色沉淀。因此,可得出结论组合物的储存稳定性不足。
[0049]对比例2:用52.3g甲苯、21gIPA和23.9g二季戊四醇六丙烯酸酯(60wt%)和二季戊四醇(单羟基)五丙烯酸酯(40wt%)的混合物填充烧瓶,并搅拌各组分。按序结合该产物与3.74g3-甲基丙烯酰氧基丙基三甲氧基硅烷、44.9g胶态二氧化硅的IPA分散液(浓度:30wt%;胶态二氧化硅颗粒的平均粒度:13nm)、0.46g水,并搅拌各组分1小时。在冷却混合物之后,添加2.25g光聚合引发剂(日本Ciba-Geigy的产品,注册商品名:IRGACURE184)和4.5mg吩噻嗪。所得产物包括丙烯酰氧基官能的硅氧烷组合物。
[0050]通过实践实施例1中所述的方法,将所得组合物施加到PET膜上。薄的固化涂层具有80°的水接触角。可得出结论该涂层具有不足的防水性。
[0051]对比例3:通过以与实践实施例1中相同的方法制备丙烯酰氧基官能的硅氧烷组合物,所不同的是使用0.2g粘度为270mm2/s和在所述分子侧链内具有聚氧亚乙基的聚二甲基硅氧烷流体(聚氧亚乙基链的含量:47wt%),而不是氨基改性的二甲基聚硅氧烷流体。
[0052]通过实践实施例1中所述的方法,将所得组合物施加到PET膜上。薄的固化涂层具有90°的水接触角。可认为该涂层具有不足的防水性。观察表明,在固化层的表面上渗出油。
[0053]以上所述的本发明组合物的特征在于优良的储存稳定性,同时通过固化该组合物获得的产品的特征在于高的抗划伤性、透明度、防水性、粘合性、耐气候性能和抗紫外线。因此,该组合物适于用作成膜剂和涂布各种基底的涂布剂。在组分(A)和(B)之间的初步反应防止油从涂布膜中渗出且防止随着时间流逝稳定性的丧失。本发明的组合物在使用薄的固化膜的各种应用中可得到应用,如在机动车车窗上的保护膜、建筑玻璃、显示器、触摸面板或磁卡;机动车头灯的透明树脂玻璃等。
Claims (6)
1.一种可通过高能辐射固化的丙烯酰氧基官能的硅氧烷组合物,它包括:
(A)至少一类多官能的丙烯酸酯;
(B)氨基改性的有机聚硅氧烷,其中组分(B)内氨基的摩尔量小于组分(A)内丙烯酸酯官能团的摩尔量;
(C)具有脂族不饱和键的有机烷氧基硅烷;
(D)胶态二氧化硅;和
(E)含醇的有机溶剂;
其中以每100重量份的组分(A)计,以1-30重量份的用量包含所述组分(B),以1-30重量份的用量包含组分(C),以1-100重量份的用量包含组分(D),和以10-1000重量份的用量包含组分(E)。
2.权利要求1的可通过高能辐射固化的丙烯酰氧基官能的硅氧烷组合物,进一步包括(G)水。
3.权利要求1的可通过高能辐射固化的丙烯酰氧基官能的硅氧烷组合物,进一步包括以每100重量份的组分(C)计,用量为1-50份的(G)水。
4.权利要求1的可通过高能辐射固化的丙烯酰氧基官能的硅氧烷组合物,其中以小于所述组分(A)重量份的1/5的用量包含所述组分(B)。
5.权利要求1的可通过高能辐射固化的丙烯酰氧基官能的硅氧烷组合物,其中所述组分(A)是五或更高官能度的丙烯酸酯。
6.权利要求1的可通过高能辐射固化的丙烯酰氧基官能的硅氧烷组合物,进一步包括至少一类光聚合引发剂(H)。
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JP059264/2003 | 2003-03-06 | ||
JP2003059264A JP4646497B2 (ja) | 2003-03-06 | 2003-03-06 | 高エネルギー線硬化性アクリロキシ官能シリコーン組成物 |
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US (1) | US8178613B2 (zh) |
EP (1) | EP1608713B1 (zh) |
JP (1) | JP4646497B2 (zh) |
KR (1) | KR101021045B1 (zh) |
CN (1) | CN1333027C (zh) |
AT (1) | ATE449143T1 (zh) |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI643911B (zh) * | 2013-11-11 | 2018-12-11 | 道康寧東麗股份有限公司 | 用於介電陶瓷形成材料之離型膜的可經高能輻射固化之丙烯醯氧官能性聚矽氧組合物與使用其之用於介電陶瓷形成材料的離型膜 |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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CN112920491B (zh) * | 2021-01-30 | 2023-06-27 | 滁州天鸿新型包装材料有限公司 | 一种epe环保包装材料的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0735066A2 (en) * | 1995-03-30 | 1996-10-02 | Dow Corning Toray Silicone Company, Limited | Radiation curable silicone release coating composition |
CN1347942A (zh) * | 2000-06-30 | 2002-05-08 | 陶氏康宁东丽硅氧烷株式会社 | 高能辐射固化组合物和树脂模塑件 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6036192B2 (ja) * | 1978-07-07 | 1985-08-19 | 信越化学工業株式会社 | 混成集積回路被覆用光重合性樹脂組成物 |
JPH0627196B2 (ja) * | 1984-03-12 | 1994-04-13 | 大日本印刷株式会社 | 放射線硬化性有機珪素化合物の製造法 |
CA2018237C (en) * | 1989-07-14 | 2000-05-09 | Antony P. Wright | Radiation curable acryloxyfunctional silicone coating composition |
CA2033637A1 (en) | 1990-01-08 | 1991-07-09 | Levi J. Cottington | Radiation curable abrasion resistant cyclic ether acrylate coating compositions |
JP3301135B2 (ja) * | 1992-12-16 | 2002-07-15 | 株式会社スリーボンド | 放射線硬化性接着性オルガノポリシロキサン組成物 |
CA2141515A1 (en) | 1994-02-08 | 1995-08-09 | John D. Blizzard | Abrasion-resistant coating |
CA2141516A1 (en) | 1994-06-13 | 1995-12-14 | John D. Blizzard | Radiation-curable oligomer-based coating composition |
EP0730015B1 (en) * | 1995-02-28 | 1999-01-13 | Dow Corning Corporation | Method for making organically-modified, radiation-curable siloxane resins |
JPH1111361A (ja) | 1997-06-25 | 1999-01-19 | Mitsubishi Agricult Mach Co Ltd | クローラ走行装置の遊動輪調節機構 |
JP2002194084A (ja) * | 2000-12-27 | 2002-07-10 | Mitsubishi Chemicals Corp | ポリシロキサン構造単位を有する化合物、活性エネルギー線硬化性被覆組成物、及び該組成物の硬化被膜を有する材料 |
-
2003
- 2003-03-06 JP JP2003059264A patent/JP4646497B2/ja not_active Expired - Lifetime
-
2004
- 2004-03-05 CN CNB200480005629XA patent/CN1333027C/zh not_active Expired - Lifetime
- 2004-03-05 DE DE602004024178T patent/DE602004024178D1/de not_active Expired - Lifetime
- 2004-03-05 EP EP04717869A patent/EP1608713B1/en not_active Expired - Lifetime
- 2004-03-05 AT AT04717869T patent/ATE449143T1/de not_active IP Right Cessation
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- 2004-03-05 KR KR1020057016536A patent/KR101021045B1/ko active IP Right Grant
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0735066A2 (en) * | 1995-03-30 | 1996-10-02 | Dow Corning Toray Silicone Company, Limited | Radiation curable silicone release coating composition |
CN1347942A (zh) * | 2000-06-30 | 2002-05-08 | 陶氏康宁东丽硅氧烷株式会社 | 高能辐射固化组合物和树脂模塑件 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI643911B (zh) * | 2013-11-11 | 2018-12-11 | 道康寧東麗股份有限公司 | 用於介電陶瓷形成材料之離型膜的可經高能輻射固化之丙烯醯氧官能性聚矽氧組合物與使用其之用於介電陶瓷形成材料的離型膜 |
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WO2004078863A1 (en) | 2004-09-16 |
KR20050118276A (ko) | 2005-12-16 |
US8178613B2 (en) | 2012-05-15 |
JP4646497B2 (ja) | 2011-03-09 |
EP1608713B1 (en) | 2009-11-18 |
KR101021045B1 (ko) | 2011-03-15 |
US20070032587A1 (en) | 2007-02-08 |
CN1756815A (zh) | 2006-04-05 |
JP2004269589A (ja) | 2004-09-30 |
EP1608713A1 (en) | 2005-12-28 |
DE602004024178D1 (de) | 2009-12-31 |
ATE449143T1 (de) | 2009-12-15 |
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