CN116783250A - 缩合固化型硅酮组合物、固化物及该固化物的制造方法 - Google Patents
缩合固化型硅酮组合物、固化物及该固化物的制造方法 Download PDFInfo
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- CN116783250A CN116783250A CN202280011220.7A CN202280011220A CN116783250A CN 116783250 A CN116783250 A CN 116783250A CN 202280011220 A CN202280011220 A CN 202280011220A CN 116783250 A CN116783250 A CN 116783250A
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- organopolysiloxane
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Abstract
[课题]本发明的目的在于提供具有固化性和保存稳定性的缩合固化型硅酮组合物。[解决手段]本发明提供缩合固化型硅酮组合物,含有具有烷氧基甲硅烷基的有机聚硅氧烷和用下述通式(1)表示的化合物。(式中,R1和R2相互独立地为氢原子、或未取代或取代的碳数1~12的一价烃基,Ar为未取代或取代的碳数6~20的芳基或碳数3~20的杂芳基,且m为0~3的整数。)此外本发明提供硅酮固化物的制造方法,包括在用上述通式(1)表示的化合物存在下使具有烷氧基甲硅烷基的有机聚硅氧烷水解缩合而得到硅酮固化物的工序。
Description
技术领域
本发明涉及缩合固化型硅酮组合物、其固化物及固化物的制造方法,更详细地说,涉及含有特定的胍化合物作为缩合催化剂的缩合固化型硅酮组合物。
背景技术
硅酮树脂由于防水性、耐热性、耐候性、耐寒性、电绝缘性、耐化学药品性以及对身体的安全性等性质优异,因此目前广泛用于各种领域。
特别是以SiO2单元(Q单元)、RSiO1.5单元(T单元)(R为烷基、苯基等有机基团)为主要成分的具有三维交联结构的有机聚硅氧烷,被称为硅酮树脂或硅酮烷氧基低聚物,利用其固化性而广泛用于涂料、涂布剂用途或粘结剂用途等。
其中,以烷氧基甲硅烷基为交联基团的液状硅酮低聚物被用作不含可燃性且对人体有害的有机溶剂的无溶剂型涂料的主剂。
另外,该烷氧基甲硅烷基由于空气中的湿气,即使在常温下也会进行交联反应。因此,对于含有烷氧基甲硅烷基的硅酮低聚物,通过掺混固化催化剂,在常温或加热条件下该烷氧基甲硅烷基反应而形成硅氧烷网络,因此可容易形成耐热性、耐候性优异的覆膜,从而被用于从室外建筑物到电子零件的广泛领域。
含有烷氧基甲硅烷基的硅酮低聚物的固化催化剂通常使用铝、钛、锌、铋、锡这样的金属催化剂,但近年来作为环境友好型的无金属催化剂,研究了胍系催化剂、胺系催化剂(专利文献1)。
现有技术文献
专利文献
专利文献1:国际公开第2018/186167号。
发明内容
发明所要解决的课题
但是,笔者研究发现,在缩合固化型硅酮组合物中使用上述胺催化剂或胍催化剂的情况下,由于其强碱性导致硅氧烷链被切断,硅酮组合物的适用期有时会显著变差。本发明是鉴于上述情况而完成的,其目的在于提供具有固化性和保存稳定性的缩合固化型硅酮组合物。
解决课题的手段
本发明人为了解决上述课题进行了深入研究,结果发现,通过将具有下述所示的特定结构的环式芳基胍化合物用作缩合催化剂,可得到能够兼顾固化性和保存稳定性的缩合固化型硅酮组合物;从而完成了本发明。
即,本发明提供缩合固化型硅酮组合物,其中,含有具有烷氧基甲硅烷基的有机聚硅氧烷和用下述通式(1)表示的化合物:
[化学式1]
式中,R1和R2相互独立地为氢原子、或未取代或取代的碳数1~12的一价烃基,Ar为未取代或取代的碳数6~20的芳基或碳数3~20的杂芳基,且m为0~3的整数。
此外,本发明提供硅酮固化物的制造方法,其中,包括在用上述通式(1)表示的化合物存在下使具有烷氧基甲硅烷基的有机聚硅氧烷水解缩合而得到硅酮固化物的工序。
发明的效果
本发明的缩合固化型硅酮组合物通过含有用上述通式(1)表示的环式芳基胍化合物作为缩合催化剂,保存稳定性优异,可形成高硬度的固化物。因此,可适合地用作减少金属催化剂量或不使用金属催化剂的环境协调型涂布剂。
具体实施方式
以下,对本发明进行详细说明。
本发明的缩合固化型硅酮组合物含有:具有烷氧基甲硅烷基的有机聚硅氧烷和用下述通式(1)表示的化合物(以下,称为环式芳基胍化合物或胍化合物)。
在本发明的组合物中,下述环式芳基胍化合物作为缩合固化型硅酮组合物的固化催化剂起作用。
[化学式2]
R1和R2相互独立地为氢原子、或未取代或取代的碳数1~12的一价烃基。碳数1~12的一价烃基可以是直链状、环状、分支状中的任一种。更详细地说,可列举出甲基、乙基、异丙基、正丙基、正丁基、仲丁基、叔丁基、正戊基、正己基、环己基、正庚基、正辛基、正壬基和正癸基等,优选甲基、乙基、异丙基、正丙基、叔丁基、仲丁基、正丁基、烯丙基、苄基,更优选甲基、乙基。作为取代的碳数1~12的一价烃基,可列举出甲氧基甲基、乙氧基甲基、丙氧基甲基、丁氧基甲基、氯甲基、氯乙基、氯丙基、氨基丙基、巯基丙基、三氟甲基、三氟乙基、三氟丙基。
m为0~3的整数,优选为0~2的整数,更优选为0或1,特别优选为0。需说明的是,m=0时,为下述结构。
[化学式3]
Ar为未取代或取代的碳数6~20的芳基或碳数3~20的杂芳基,芳基可列举出苯基、萘基、蒽基和芘基等,杂芳基可列举出吡啶基、噻吩基、吲哚基、三嗪、吡嗪和嘧啶等,优选吡啶基、噻吩基、吲哚基,特别优选为吡啶基。优选为未取代或取代的碳数6~16的芳基或碳数5~16的杂芳基。更优选为未取代或取代的碳数6~12的芳基或吡啶基,特别优选为未取代或取代的苯基或吡啶基,最优选为未取代或取代的苯基。
芳基或杂芳基可具有取代基,该取代基没有特别限定,可例示出甲基、乙基、异丙基、正丙基、正丁基、仲丁基、叔丁基、正戊基、正己基、正庚基、正辛基、正壬基和正癸基等烷基,环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基和环癸基等环烷基,乙烯基、烯丙基、丁烯基和戊烯基等烯基,苯基和萘基等芳基,氟、氯、溴和碘基等卤代基,硝基、氰基、氨基、单烷基氨基、二烷基氨基和吡啶基等含氮取代基,甲氧基、乙氧基、丙氧基、丁氧基、苯氧基、萘氧基、呋喃基和羟基等含氧取代基,硫醇、硫醚和噻吩基等含硫取代基,以及三氟烷基等含卤素取代基。
另外,通过在Ar基上经由连接链导入烷氧基甲硅烷基,则即使是能够与硅酮成键的结构,也不会对本发明的效果有任何妨碍。Ar基上的取代基的取代数和取代基的键合部位也是任意的,在上述取代基上可进一步具有任意的取代基。
作为这样的环式芳基胍化合物,可例示出以下化合物。
[化学式4]
上述环式芳基胍化合物可通过以下方法制造:通过使用下述结构式(1a)表示的脲衍生物与氯化剂反应,来合成Vilsmeier盐(1b),并使其与用下述结构式(1c)表示的芳基伯胺反应。
[化学式5]
HN——Ar(1c)
作为氯化剂,例如可列举出草酰氯、磷酰氯、亚硫酰氯等,从反应性的观点出发,优选草酰氯、磷酰氯,特别优选草酰氯。为了合成Vilsmeier盐,优选相对于1摩尔的脲衍生物,加入1~5当量、优选为1~3当量、更优选为1~1.5当量的氯化剂,在0℃~100℃的温度范围内反应1~48小时。
在使Vilsmeier盐(1b)与苯胺衍生物(1c)反应时,优选相对于1摩尔的Vilsmeier盐(1b),加入0.5~5当量、优选为0.7~3当量、更优选为0.8~1.5当量的苯胺衍生物(1c),在0~100℃的温度范围内反应1~24小时。
上述环式芳基胍化合物的合成可在有机溶剂的存在下进行。作为有机溶剂,只要是与上述各原料化合物相容,且不与Vilsmeier盐反应的有机溶剂,则没有特别限制。例如,可列举出甲苯、二甲苯等芳族烃类,己烷、辛烷等烃类,甲乙酮、甲基异丁基酮等酮类,乙酸乙酯、乙酸异丁酯等酯类等。
在使用有机溶剂的情况下,其使用量没有特别限制,通常相对于原料化合物的总质量1质量份,优选为20质量份以下,更优选为0.5~10质量份,更进一步优选为1~5质量份。
作为脲衍生物(1a),优选N,N’-二甲基咪唑烷酮、N,N’-二乙基咪唑烷酮、N,N’-二(甲氧基甲基)咪唑烷酮、N,N’-二丙基咪唑烷酮、N-甲基-N’-乙基咪唑烷酮、N,N’-二甲基丙撑脲、N,N’-二乙基丙撑脲、N,N’-二丙基丙撑脲和N-甲基-N’-乙基丙撑脲,若考虑原料的易获取性,则优选N,N’-二乙基咪唑烷酮、N,N’-二甲基丙撑脲。
作为芳基伯胺(1c),例如可列举出苯胺、茴香胺、苯氧基苯胺、羟基苯胺、(羟基甲基)苯胺、均三甲苯胺、甲苄胺、三氟甲基苯胺、N,N’-二甲基氨基苯胺、硝基苯胺、氰基苯胺、甲苯胺、乙基苯胺、二甲基苯胺、二乙基苯胺、苄基苯胺、氯苯胺、氟苯胺、溴苯胺、碘苯胺、六氟苯胺、乙烯基苯胺、乙炔基苯胺、氨基苯硫酚、氨基吡啶、氨基噻吩、氨基吡咯和氨基呋喃。若考虑原料的易获取性,则优选苯胺、茴香胺、甲苯胺和均三甲苯胺。
上述环式胍化合物通过掺混到含有具有烷氧基甲硅烷基的有机聚硅氧烷的缩合固化型硅酮组合物中而作为固化催化剂起作用。在该环式胍化合物的存在下,具有烷氧基甲硅烷基的有机聚硅氧烷水解缩合固化。特别是可在空气中的湿气存在下进行水解缩合。
胍化合物的添加量没有特别限定,但若考虑将固化速度调整到适当的范围以制作所期望的物性的固化皮膜,并且提高涂布时的操作性,此外考虑经济性等,则相对于100质量份的具有烷氧基甲硅烷基的有机聚硅氧烷,优选为0.1~15质量份,更优选为0.5~10质量份,更进一步优选为1~5质量份。
作为具有烷氧基甲硅烷基的有机聚硅氧烷,例如可使用在末端具有烷氧基甲硅烷基的低聚物。有机聚硅氧烷的结构可使用具有链状、环状、分支状等硅氧烷结构的聚合物,从耐开裂性的观点出发,优选具有环状结构的有机聚硅氧烷。
作为所述具有烷氧基甲硅烷基的有机聚硅氧烷,只要是1分子中具有1个以上的烷氧基甲硅烷基的有机聚硅氧烷,则没有特别限制,若考虑形成更高硬度的覆膜,则优选1分子中具有2个以上的烷氧基甲硅烷基的有机聚硅氧烷。
具有烷氧基甲硅烷基的有机聚硅氧烷的运动粘度没有特别限定,优选为10~10,000mm2/s,更优选为10~1,000mm2/s,从操作性的观点出发,特别优选为10~200mm2/s。运动粘度是用奥氏粘度计测得的25℃下的测定值。
具有环状结构的有机聚硅氧烷优选为选自用下述通式(2)表示的环状烷氧基硅氧烷及其水解缩合物中的1种以上。
[化学式6]
式中,R3相互独立地为未取代或取代的碳数1~8的一价烃基,R4相互独立地为未取代或取代的碳数1~3的一价烃基,且n为1~3的整数。
作为R3的碳数1~8的一价烃基可列举出甲基、乙基、异丙基、正丙基、正丁基、仲丁基、叔丁基、正戊基、正己基、正庚基、正辛基、环己基、苯基、萘基和乙烯基等,优选甲基、乙基和苯基。取代的碳数1~8的一价烃基可列举出(环氧环己基)乙基、缩水甘油氧基丙基、甲基丙烯酰氧基丙基、丙烯酰氧基丙基、氨基丙基、巯基丙基、氯甲基、氯乙基、氯丙基、氯丁基、氯戊基、氯己基、三氟甲基、三氟乙基、三氟丙基。
作为R4的碳数1~3的一价烃基可列举出甲基、乙基、异丙基、正丙基等,优选甲基和乙基。取代的碳数1~3的一价烃基可列举出氯甲基、氯乙基、氯丙基、三氟甲基、三氟乙基、三氟丙基、乙酰氧基、丙酰氧基。
这样的环状烷氧基硅氧烷优选可列举出以下物质。
[化学式7]
具有烷氧基甲硅烷基的有机聚硅氧烷可以是烷氧基硅烷的部分水解缩合物。
作为烷氧基硅烷,优选具有1~4个、优选2或3个碳数1~6、优选碳数1~4的烷氧基的烷氧基硅烷。例如可列举出二甲基二甲氧基硅烷、二甲基二乙氧基硅烷、二甲基二异丙氧基硅烷、二甲基二丁氧基硅烷、二甲基二异丙烯氧基硅烷、丙基甲基二甲氧基硅烷、己基甲基二甲氧基硅烷、苯基甲基二甲氧基硅烷、二苯基二甲氧基硅烷、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、甲基三丁氧基硅烷、甲基三异丙烯氧基硅烷、乙基三甲氧基硅烷、乙基三乙氧基硅烷、丁基三甲氧基硅烷、己基三甲氧基硅烷、癸基三甲氧基硅烷、苯基三甲氧基硅烷、环己基三甲氧基硅烷、四甲氧基硅烷、四乙氧基硅烷。
此外,也可使用乙烯基甲基二甲氧基硅烷、乙烯基甲基二乙氧基硅烷、3-缩水甘油氧基丙基甲基二甲氧基硅烷、3-缩水甘油氧基丙基甲基二乙氧基硅烷、3-(甲基)丙烯酰氧基丙基甲基二甲氧基硅烷、3-(甲基)丙烯酰氧基丙基甲基二乙氧基硅烷、3-氨基丙基甲基二甲氧基硅烷、3-氨基丙基甲基二乙氧基硅烷、3-巯基丙基甲基二甲氧基硅烷、3-巯基丙基甲基二乙氧基硅烷、乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、5-己烯基三甲氧基硅烷、3-缩水甘油氧基丙基三甲氧基硅烷、3-缩水甘油氧基丙基三乙氧基硅烷、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、4-乙烯基苯基三甲氧基硅烷、3-(4-乙烯基丙基)丙基三甲氧基硅烷、4-乙烯基苯基甲基三甲氧基硅烷、3-氨基丙基三甲氧基硅烷、3-氨基丙基三乙氧基硅烷、3-(2-氨基乙基)氨基丙基三甲氧基硅烷、3-巯基丙基三甲氧基硅烷、3-巯基丙基三乙氧基硅烷等具有反应性官能团的烷氧基硅烷。
作为烷氧基硅烷,其中,甲氧基硅烷、乙氧基硅烷由于副产物易挥发而优选,甲基三甲氧基硅烷、二甲基二甲氧基硅烷由于反应性高而优选。
另外,也可将上述烷氧基硅烷和用上述式(2)表示的环状烷氧基硅氧烷水解缩合,来制造具有烷氧基甲硅烷基的有机聚硅氧烷。在环状烷氧基硅氧烷的水解缩合中优选使用酸催化剂。酸催化剂只要是具有足以使烷氧基甲硅烷基水解、并使生成的硅烷醇通过脱水缩合形成硅氧烷键的酸度的物质即可,没有特别限定。优选pKa在-2.9~0的范围内的酸催化剂,特别优选pKa在-2.9~0的范围内的磺酸系催化剂。
酸催化剂可采用液体、固体和气体中的任意形态,不特别限定形态。例如,可列举出碳数1~14的取代或未取代的烷基磺酸、碳数6~30的取代或未取代的苯磺酸及其水合物、碳数6~30的取代或未取代的萘磺酸及其水合物、取代或未取代的樟脑磺酸、含有磺基的固体酸、硝酸等。其中,优选甲磺酸、乙磺酸、樟脑磺酸、对甲苯磺酸、苯磺酸、二壬基萘二磺酸(DNNDSA)、二壬基萘(单)磺酸(DNNSA)、十二烷基苯磺酸(DDBSA),特别优选甲磺酸、对甲苯磺酸、苯磺酸、二壬基萘二磺酸(DNNDSA)、二壬基萘(单)磺酸(DNNSA)、十二烷基苯磺酸(DDBSA)。酸催化剂的使用量通常优选为聚合反应体系的总质量的0.001~10质量%,更优选为0.01~5质量%,特别优选为0.1~2.5质量%。
水解缩合反应可在无溶剂下进行,但也可使用例如甲醇、乙醇、异丙醇、丁醇、双丙酮醇、丙二醇单甲醚、丙二醇单甲醚乙酸酯、丙酮、甲苯和二甲苯等有机溶剂。在使用有机溶剂的情况下,其量没有特别限制,相对于合计1质量份的硅烷和烷氧基硅氧烷,优选为20质量份以下,更优选为0.25~10质量份,进一步优选为0.5~5质量份。
反应中使用的水的量,通常相对于反应体系中含有的烷氧基甲硅烷基1摩尔,优选为0.025~5.0摩尔,更优选为0.05~2.5摩尔,更进一步优选为0.075~1.0摩尔。
反应温度没有特别限制,通常为0~150℃,优选为20~120℃,更优选为40~100℃,更进一步优选为50~80℃。反应时间通常为1小时以上,优选为2~72小时。
优选通过蒸馏操作除去因烷氧基甲硅烷基的水解缩合反应而副产的醇、未反应的原料和低分子硅氧烷,其温度和压力只要是可除去这些杂质的条件,则没有特别限制,通常为10~150℃,优选为60~120℃,可在大气压或减压下进行。
需说明的是,本发明的缩合固化型硅酮组合物可在不妨碍本发明效果的范围内适当地加入任意的添加剂
作为这样的添加剂的具体例,可列举出溶剂、非反应性硅油、反应性硅油、硅烷偶联剂等粘附促进剂、抗老化剂、防锈剂、着色剂、表面活性剂、流变调节剂、紫外线吸收剂、红外线吸收剂、荧光剂、研磨剂、香料、填充剂、流平剂、反应性稀释剂、非反应性高分子树脂、抗氧化剂、紫外线吸收剂、光稳定剂、消泡剂、分散剂、抗静电剂、触变剂等。
另外,为了补充胍化合物的催化活性,也可并用金属系固化催化剂。作为金属系固化催化剂,可列举出二丁基氧化锡、二辛基氧化锡等烷基锡化合物,二乙酸二丁基锡、二月桂酸二丁基锡、二月桂酸二辛基锡、二辛酸二丁基锡、二辛酸二辛基锡、二新癸酸二辛基锡等烷基锡酯化合物,四异丙醇钛、四正丁醇钛、四(2-乙基己醇)钛、四叔丁醇钛、二丙氧基双(乙酰丙酮)合钛、双(乙基乙酰乙酸根)二异丙氧化钛、异丙氧基辛二醇钛等钛酸酯、和钛螯合化合物以及它们的部分水解物,环烷酸锌、硬脂酸锌、2-乙基辛酸锌、2-乙基己酸铁、2-乙基己酸钴、2-乙基己酸锰、环烷酸钴、乙酰丙酮铝、双(乙基乙酰乙酸)单正丁酸铝、乙基乙酰乙酸二正丁酸铝、三(乙基乙酰乙酸根合)铝等铝化合物及其水解物,其中,从催化活性的观点出发,优选四异丙醇钛、四正丁醇钛、四(2-乙基己醇)钛、四叔丁醇钛、二丙氧基双(乙酰丙酮)合钛、双(乙基乙酰乙酸根)二异丙氧化钛、四(乙酰丙酮)合钛、四(乙基乙酰乙酸根合)钛、四(甲基乙酰乙酸根合)钛、四(二乙基丙二酸根合)钛、四(二甲基丙二酸根合)钛及它们的部分水解物。在金属系固化催化剂被并用的情况下,其量相对于100质量份的缩合固化型硅酮组合物,可为0.01~5质量份,优选为0.05~3质量份,特别优选为0.1~2质量份。
通过将本发明的缩合固化型硅酮组合物涂布在基材的表面并使其固化,可得到具有由固化物构成的被覆层的物品。作为涂布方法,没有特别限定。例如,可从喷涂、旋涂、浸涂、辊涂、刷涂、棒涂和流涂等公知的方法中适当选择使用。
作为基材,可列举出环氧树脂、酚醛树脂、聚碳酸酯类和聚碳酸酯共混物、聚(甲基丙烯酸甲酯)等丙烯酸系树脂、聚(对苯二甲酸乙二醇酯)、聚(对苯二甲酸丁二醇酯)、不饱和聚酯树脂等聚酯树脂、聚酰胺树脂、聚酰亚胺树脂、丙烯腈-苯乙烯共聚物、苯乙烯-丙烯腈-丁二烯共聚物、聚氯乙烯树脂、聚苯乙烯树脂、聚苯乙烯与聚苯醚共混物、醋酸丁酸纤维素、聚乙烯树脂等有机聚合物基材,钢板等金属基材,涂料涂布面、玻璃、陶瓷、混凝土、板岩板、纺织品、木材、石材、瓦、(中空)二氧化硅、二氧化钛、氧化锆、氧化铝等无机填料,以玻璃纤维为代表的玻璃布、玻璃带、玻璃纤维板、玻璃纸等玻璃纤维制品等,对于基材的材质和形状,没有特别限定,但本发明的固化性组合物可特别适合地用于钢板、玻璃的被覆。
本发明的缩合固化型硅酮组合物通过与气氛中的水分接触,进行具有烷氧基甲硅烷基的有机聚硅氧烷的水解缩合反应,从而引发固化反应。作为气氛中的水分的指标,可以是10~100%RH的任意湿度,虽然空气中的湿气就足够了,但一般湿度越高水解进行得越快,因此根据需要可在气氛中加入水分,也可在组合物中添加水。固化反应温度和时间可根据所使用的基材、水分浓度、催化剂浓度和水解性基团的种类等因素适当变更。固化温度优选为-10~200℃,特别优选为0~150℃,可在不超过基材的耐热温度的范围内进行加热处理。固化时间通常在不超过所使用的基材的耐热温度的范围内为1分钟~1周左右。本发明的缩合固化型硅酮组合物即使在常温下也进行固化,形成硬度优异的覆膜。另外,若提高湿度,则固化性有提高的倾向。本发明的缩合固化型硅酮组合物与使用以往的胺催化剂或胍系催化剂的情况相比,其特征在于,在室温下稳定性优异。
实施例
以下示出实施例和比较例,对本发明进行更详细的说明,但本发明不限于下述实施例。
在下述中,运动粘度是用奥氏粘度计测得的25℃下的测定值。
[1]具有烷氧基甲硅烷基的有机聚硅氧烷的制造
[合成例1-1]
依据国际公开第2007/140012号记载的[段落0104]实施例26的程序,得到用下述结构式(2A)表示的环状烷氧基硅氧烷(有机聚硅氧烷1)(2,4,6,8-四甲氧基-2,4,6,8-四甲基环四硅氧烷)。
[化学式8]
[合成例1-2]
向具备搅拌器、回流冷却器、滴液漏斗和温度计的1,000mL可分离式烧瓶中装入361g的在合成例1中得到的用上述式(2A)表示的环状烷氧基硅氧烷和361g的甲苯,边搅拌边加入3.6g的甲磺酸。然后,继续用1小时滴加13.5g的离子交换水。滴加结束后,在25℃下聚合2小时。向所得的液体中加入18.0g的KYOWAAD 500SN(协和化学工业公司制),在25℃下搅拌2小时进行中和后,减压蒸馏除去残存甲醇和低分子成分,得到上述环状烷氧基硅氧烷的水解缩合物(有机聚硅氧烷2)。
所得的有机聚硅氧烷2的运动粘度为49mm2/s。
[合成例1-3]
向具备搅拌器、回流冷却器、滴液漏斗和温度计的1,000mL可分离式烧瓶中装入289g的在合成例1中得到的用上述式(2A)表示的环状烷氧基硅氧烷、96g的二甲基二甲氧基硅烷、385g的甲苯,边搅拌边加入4.0g的甲磺酸后,继续用1小时滴加13.0g的离子交换水。滴加结束后,在25℃下聚合2小时。向所得的液体中加入20.0g的KYOWAAD 500SN(协和化学工业公司制),在25℃下搅拌2小时进行中和后,减压蒸馏除去残存甲醇和低分子成分,得到上述环状烷氧基硅氧烷与二甲基二甲氧基硅烷的水解缩合物(有机聚硅氧烷3)。
所得的有机聚硅氧烷3的运动粘度为31mm2/s。
[2]胍化合物的制造
[合成例2-1]
向具备搅拌器、回流冷却器、滴液漏斗和温度计的100mL可分离式烧瓶中加入14.0g的草酰氯、11.4g的二甲基咪唑烷酮、28g的甲苯,在氮气流下于室温反应12小时。向所得的液体中加入9.3g的苯胺、20.0g的三乙胺,在氮气流下于室温反应2小时。向反应液中投入100g的水,向水层中加入1N盐酸使pH为7,用甲苯清洗水层。然后,向水层中加入1N氢氧化钠水溶液来使pH为14,在该状态下用甲苯提取目标物,并加压蒸馏除去甲苯,由此得到用下述式(3a)表示的胍化合物1。
[化学式9]
[合成例2-2]
在合成例2-1中,使用12.3g的茴香胺代替苯胺,除此之外重复合成例2-1,得到用下述式(3b)表示的胍化合物2。
[化学式10]
[合成例2-3]
在合成例2-1中,使用9.4g的2-氨基吡啶代替苯胺,除此之外重复合成例2-1,得到用下述式(3c)表示的胍化合物3。
[化学式11]
[合成例2-4]
在合成例2-1中,使用13.5g的均三甲苯胺代替苯胺,除此之外重复合成例2-1,得到用下述式(3d)表示的胍化合物4。
[化学式12]
[合成例2-5]
在合成例2-1中,使用17.1g的二甲基丙撑脲代替二甲基咪唑烷酮,除此之外重复合成例2-1,得到用下述式(3e)表示的胍化合物5。
[化学式13]
[比较合成例2-6]
在合成例2-1中,使用12.7g的四甲基脲代替二甲基咪唑烷酮,除此之外重复合成例2-1,得到用下述式(3f)表示的胍化合物6。
[化学式14]
[3]缩合固化型硅酮组合物的制造
[实施例1~7和比较例1~4]
使用搅拌器将100质量份的上述合成例1-1~1-3中得到的有机聚硅氧烷以及下述表1中记载的掺混量的上述合成例2-1~2-6中得到的胍化合物或下述表1所示的缩合催化剂均匀混合,制备缩合固化型硅酮组合物。在25℃、50%RH的空气下使用5号刮棒涂布机将0.2g的所得缩合固化型硅酮组合物(即,涂布剂)涂布在玻璃板上,在25℃、50%RH的气氛下固化7天。
依据下述测定并评价所得固化物的铅笔硬度和缩合固化型硅酮组合物的保存稳定性。
[铅笔硬度]
按照基于JIS K 5600-5-4所记载的铅笔划痕试验的方法,施加750g的载荷来测定上述固化后的覆膜(10μm)的铅笔硬度。
[保存稳定性]
将10g的上述缩合固化型硅酮组合物在80℃下在玻璃瓶中密封保存24天后,目视确认有无凝胶化。未凝胶化的样品记作〇,凝胶化的样品记作×。将结果示出于表1中。
[表1]
如表1所示,实施例1~9的缩合固化型硅酮组合物具有良好的保存稳定性,形成高硬度的覆膜。另一方面,在掺混了比较例1~4那样的脒、不具有环式结构的胍、或胺催化剂的情况下,缩合固化型硅酮组合物随着时间推移而凝胶化,保存稳定性差。
产业上的可利用性
本发明的缩合固化型硅酮组合物由于含有环式芳基胍化合物作为缩合催化剂,保存稳定性优异,可形成高硬度的固化物。因此,可适合地用作减少金属催化剂量或不使用金属催化剂的环境协调型涂布剂。
Claims (11)
1.缩合固化型硅酮组合物,其中,含有具有烷氧基甲硅烷基的有机聚硅氧烷和用下述通式(1)表示的化合物:
[化学式1]
式中,R1和R2相互独立地为氢原子、或未取代或取代的碳数1~12的一价烃基,Ar为未取代或取代的碳数6~20的芳基或碳数3~20的杂芳基,且m为0~3的整数。
2.根据权利要求1所述的缩合固化型硅酮组合物,其中,所述具有烷氧基甲硅烷基的有机聚硅氧烷为选自用下述通式(2)表示的环状烷氧基硅氧烷、其水解缩合物、和用下述通式(2)表示的环状烷氧基硅氧烷与烷氧基硅烷的水解缩合物中的1种以上:
[化学式2]
式中,R3相互独立地为未取代或取代的碳数1~8的一价烃基,R4相互独立地为未取代或取代的碳数1~3的一价烃基,且n为1~3的整数。
3.根据权利要求1或2所述的缩合固化型硅酮组合物,其中,所述用通式(1)表示的化合物的量相对于100质量份的具有烷氧基甲硅烷基的有机聚硅氧烷为0.1~15质量份。
4.根据权利要求1~3中任一项所述的缩合固化型硅酮组合物,其中,在所述式(1)中Ar为取代或未取代的苯基或吡啶基。
5.根据权利要求4所述的缩合固化型硅酮组合物,其中,所述Ar为:苯基,或与苯基的碳原子键合的氢原子中的至少1个被烷基、环烷基、烯基、芳基、卤素原子、含氮取代基、含氧取代基、含硫取代基或含卤素取代基置换而得的基团,或吡啶基。
6.固化物,所述固化物是将根据权利要求1~5中任一项所述的缩合固化型硅酮组合物固化而成的。
7.硅酮固化物的制造方法,其中,包括在用下述通式(1)表示的化合物存在下,使具有烷氧基甲硅烷基的有机聚硅氧烷水解缩合而得到硅酮固化物的工序:
[化学式3]
式中,R1和R2相互独立地为氢原子、或未取代或取代的碳数1~12的一价烃基,Ar为未取代或取代的碳数6~20的芳基或碳数3~20的杂芳基,且m为0~3的整数。
8.根据权利要求7所述的制造方法,其中,所述具有烷氧基甲硅烷基的有机聚硅氧烷为选自用下述通式(2)表示的环状烷氧基硅氧烷、其水解缩合物、和用下述通式(2)表示的环状烷氧基硅氧烷与烷氧基硅烷的水解缩合物中的1种以上:
[化学式4]
式中,R3相互独立地为未取代或取代的碳数1~8的一价烃基,R4相互独立地为未取代或取代的碳数1~3的一价烃基,且n为1~3的整数。
9.根据权利要求7或8所述的制造方法,其中,所述用通式(1)表示的化合物的量相对于100质量份的具有烷氧基甲硅烷基的有机聚硅氧烷为0.1~15质量份。
10.根据权利要求7~9中任一项所述的制造方法,其中,在所述式(1)中Ar为取代或未取代的苯基或吡啶基。
11.根据权利要求10所述的制造方法,其中,所述Ar为:与苯基的碳原子键合的氢原子中的至少1个被烷基、环烷基、烯基、芳基、卤素原子、含氮取代基、含氧取代基、含硫取代基或含卤素取代基置换而得的基团,或吡啶基。
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