CN115926058A - 聚酰胺酰亚胺(甲基)丙烯酸酯树脂、活性能量线硬化型树脂组合物及其硬化物 - Google Patents
聚酰胺酰亚胺(甲基)丙烯酸酯树脂、活性能量线硬化型树脂组合物及其硬化物 Download PDFInfo
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- CN115926058A CN115926058A CN202211160248.5A CN202211160248A CN115926058A CN 115926058 A CN115926058 A CN 115926058A CN 202211160248 A CN202211160248 A CN 202211160248A CN 115926058 A CN115926058 A CN 115926058A
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- meth
- acrylate
- polyamideimide
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- resin
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- 239000004962 Polyamide-imide Substances 0.000 title claims abstract description 53
- 229920002312 polyamide-imide Polymers 0.000 title claims abstract description 53
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- -1 acrylate compound Chemical class 0.000 claims abstract description 57
- 239000011347 resin Substances 0.000 claims abstract description 36
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- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 20
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- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 16
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- 239000000203 mixture Substances 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 54
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
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- 229920006267 polyester film Polymers 0.000 description 3
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/065—Polyamides; Polyesteramides; Polyimides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
Abstract
本发明涉及聚酰胺酰亚胺(甲基)丙烯酸酯树脂、活性能量线硬化型树脂组合物及其硬化物,有鉴于背景技术的段落所述的现状的技术问题,本发明以提供一种胶粘性、硬度、硬化收缩性、耐湿热性优异的聚酰胺酰亚胺(甲基)丙烯酸酯树脂为目的。本发明所提供的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A)是使于一分子中具有环氧基的(甲基)丙烯酸酯化合物(b)与末端具有酸基或酸酐基的聚酰胺酰亚胺树脂(a3)反应而得,且该末端具有酸基或酸酐基的聚酰胺酰亚胺树脂(a3)为通过脂环族异三聚氰酸酯型聚异氰酸酯(a1)与脂环族三羧酸酐(a2)的反应而得到。
Description
技术领域
本发明关于聚酰胺酰亚胺(甲基)丙烯酸酯树脂及使用该聚酰胺酰亚胺(甲基)丙烯酸酯树脂的活性能量线硬化型树脂组合物。本发明的聚酰胺酰亚胺(甲基)丙烯酸酯树脂适合使用在粘合剂树脂、交联剂、硬涂材料。
背景技术
通过紫外线或电子束等活性能量线的照射来构成形成交联结构并硬化的组合物等的物质有其重要性,这样的技术被使用在住宅建设领域、土木及建筑领域、电气电子及信息领域、运输领域等的复合材料基质、注模材料、印墨、涂覆剂、涂料、接着剂等各种用途,产业上极为有用。于此硬化型树脂组合物中,通过使用具备多个具有反应性官能团的化合物,于硬化后形成交联结构,可得到玻璃转移点(Tg)提高,耐热性或耐溶剂性等物性优异的硬化物。
以往,(甲基)丙烯酸酯低聚物或(甲基)丙烯酸酯单体被广泛地使用作为硬化型树脂,尤其,已经以提升硬化后的被膜的柔软性或弹性模数为目的而积极地进行(甲基)丙烯酸环氧酯或氨酯(甲基)丙烯酸酯的开发。
例如于专利文献1中,记载有使用了(甲基)丙烯酸酯低聚物或(甲基)丙烯酸酯单体的硬化性树脂相对于基材的密合性、透明性、硬化性优异的内容,但这些硬化性树脂在硬化时的硬化收缩大,存在有从基材的剥离或硬化物的变形等技术问题。于专利文献2中,记载有使用了氨酯(甲基)丙烯酸酯等硬化性树脂,其于柔软性或是硬化收缩的抑制而言为优异的内容,但硬度或耐湿热性仍有技术问题存在。于专利文献3中,揭示有使用了酰胺酰亚胺(甲基)丙烯酸酯等硬化树脂,其溶剂溶解性或耐热性优异的内容,但耐湿热性仍有技术问题存在。
[现有技术文献]
[专利文献]
[专利文献1]日本特开第2012-144641号公报
[专利文献2]日本特许第2964267号公报
[专利文献3]日本特许第6669311号公报。
发明内容
[发明所欲解决的技术问题]
本发明有鉴于上述现状,以提供一种胶粘性、硬度、硬化收缩性、耐湿热性优异的聚酰胺酰亚胺(甲基)丙烯酸酯树脂为目的。
[以解决技术问题的技术手段]
本发明人等进行精心探讨,结果发现:通过脂环族异三聚氰酸酯型聚异氰酸酯(a1)与脂环族三羧酸酐(a2)的反应而得到末端具有酸基或酸酐基的聚酰胺酰亚胺树脂(a3),再使于一分子中具有环氧基的(甲基)丙烯酸酯化合物(b)与前述末端具有酸基或酸酐基的聚酰胺酰亚胺树脂(a3)而得到的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A),可提供一种干燥后的胶粘性优异,能够通过活性能量线的照射而硬化,并且硬化后的硬度、硬化收缩性、耐湿热性达到良好的硬化性组合物,因而完成本发明。
也就是,本发明关于下述[1]至[5]。
[1]一种聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A),使于一分子中具有环氧基的(甲基)丙烯酸酯化合物(b)与末端具有酸基或酸酐基的聚酰胺酰亚胺树脂(a3)反应而得,该末端具有酸基或酸酐基的聚酰胺酰亚胺树脂(a3)是通过脂环族异三聚氰酸酯型聚异氰酸酯(a1)与脂环族三羧酸酐(a2)的反应而得。
[2]如[1]所述的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A),其中前述含有环氧基之的甲基丙烯酸酯化合物(b)与前述脂环族三羧酸酐(a2)的摩尔比((b)/(a2))为0.8至2.0。
[3]一种活性能量线硬化型树脂组合物,含有:如[1]或[2]所述的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A)、光聚合引发剂(B)以及有机溶剂(C)。
[4]如[3]所述的活性能量线硬化型树脂组合物,其中,含有前述聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A)以外的光聚合性单体(D)。
[5]如[3]或[4]所述的活性能量线硬化型树脂组合物,其硬涂材料用活性能量线硬化型树脂组合物。
[6]一种硬化物,[3]至[5]中任一项所述的活性能量线硬化型树脂组合物的硬化物。
[发明的效果]
根据本发明,可提供一种硬度、低硬化收缩性、耐湿热性优异的聚酰胺酰亚胺(甲基)丙烯酸酯树脂。
具体实施方式
以下详细地说明用以实施本发明的型态(以下称为“本实施方式”)。以下的本实施方式为用以说明本发明的例示,并非将本发明限定于下列内容之意。本发明于该主旨的范围内,可适当地变形来实施。
本发明关于一种聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A),是使于一分子中具有环氧基的(甲基)丙烯酸酯化合物(b)与末端具有酸基或酸酐基的聚酰胺酰亚胺树脂(a3)反应而得,该末端具有酸基或酸酐基的聚酰胺酰亚胺树脂(a3)是通过脂环族异三聚氰酸酯型聚异氰酸酯(a1)与脂环族三羧酸酐(a2)的反应而得到。
前述脂环族异三聚氰酸酯型聚异氰酸酯(a1)是在三聚化催化剂存在下或非存在下,将含有脂环族二异氰酸酯化合物的二异氰酸酯化合物进行异三聚氰酸酯化而得到。
本说明书中所谓的脂环族,在本发明的上下文中,意指碳原子配置于环中的化合物(正如通过将“脂肪族”及“环状”的两个用语并述而暗示的内容)。因此,所谓脂环族,也为环状脂肪族的同义词。结果而言,脂环族化合物属于同素环化合物群,在此情形时包含环烷、环烯及环炔。芳香族化合物及杂环化合物以及杂环化合物的饱和化合物例,在本发明的涵义的范围内并不被视为脂环族。
前述含有脂环族二异氰酸酯化合物的二异氰酸酯化合物可列举例如:异佛尔酮二异氰酸酯、氢化甲苯二异氰酸酯、氢化二甲苯二异氰酸酯、降莰烷二异氰酸酯、氢化二苯基甲烷二异氰酸酯等。
前述三聚化催化剂并无特别指定,可列举例如:2,4,6-参(二甲基胺基甲基)酚、2,4-双(二甲基胺基甲基)酚、2,4,6-参(二烷基胺基烷基)六氢-S-三嗪等胺化合物;乙酸钾、2-乙基己酸钾、辛酸钾般的碳数2至12的羧酸的碱金属盐;羧酸的季铵盐等。市面贩卖品可列举:DABCO P15(Sankyo Film Air Products公司制)、DABCO K15(Sankyo Film AirProducts公司制)、PELCAT 9540(Perlon公司制)、DABCO TMR(Sankyo Film Air Products公司制)、TOYOCAT TR20(Tosoh公司制)、U-CAT 18X(Sun Apro公司制)等。
前述脂环族异三聚氰酸酯型聚异氰酸酯(a1)可列举例如:从异佛尔酮二异氰酸酯所合成的脂环族异三聚氰酸酯型三异氰酸酯(包含五聚体等聚合物)、从氢化甲苯二异氰酸酯所合成的脂环族异三聚氰酸酯型三异氰酸酯(包含五聚体等聚合物)、从氢化二甲苯二异氰酸酯所合成的脂环族异三聚氰酸酯型三异氰酸酯(包含五聚体等聚合物)、从降莰烷二异氰酸酯所合成的异三聚氰酸酯型三异氰酸酯(包含五聚体等聚合物)、从氢化二苯基甲烷二异氰酸酯所合成的脂环族异三聚氰酸酯型三异氰酸酯(包含五聚体等聚合物)等。当中较优选为从异佛尔酮二异氰酸酯所合成的脂环族异三聚氰酸酯型异氰酸酯。通过使用前述脂环族异三聚氰酸酯型聚异氰酸酯(a1),得到胶粘性或硬化收缩优异的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A)。
前述脂环族三羧酸酐(a2)可列举环己烷-1,3,4-三羧酸-3,4-酐、环己烷-1,3,5-三羧酸-3,5-酐、环己烷-1,2,3-三羧酸-2,3-酐等。当中较优选为环己烷-1,3,4-三羧酸-3,4-酐。通过使用前述脂环族三羧酸酐(a2),得到胶粘性或硬化收缩优异的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A)。
前述脂环族异三聚氰酸酯型聚异氰酸酯(a1)与前述脂环族三羧酸酐(a2)的反应中,相对于前述脂环族异三聚氰酸酯型聚异氰酸酯(a1)所具有的异氰酸酯基1mol,酸酐基与羧酸的合计较优选为设成1mol以上,尤优选为1.2mol以上,更优选为1.4mol以上。以1.4mol以上来使用时,末端具有酸基或酸酐基的聚酰胺酰亚胺树脂(a3)具有所得到的硬化物的硬度或胶粘性优异的效果。此可考量为以1.4mol以上来使用时,由于实质上不含氨酯键,所以容易控制反应之故。
前述于一分子中具有环氧基的(甲基)丙烯酸酯化合物(b),只要是于分子结构中具有(甲基)丙烯酰基与环氧基的化合物,其它具体的结构就无特别限定,可使用各式各样的化合物。其一例可列举例如:缩水甘油(甲基)丙烯酸酯、(甲基)丙烯酸4-羟基丁酯缩水甘油醚、(甲基)丙烯酸环氧环己基甲酯等含有缩水甘油基的(甲基)丙烯酸酯单体;二羟基苯二缩水甘油醚、二羟基萘二缩水甘油醚、联苯酚二缩水甘油醚、双酚二缩水甘油醚等二缩水甘油醚化合物的单(甲基)丙烯酸酯化合物等。这些含有环氧基的(甲基)丙烯酸酯化合物可单独使用,也可并用2种以上。这些当中,由于容易控制反应,故较优选为具有1个环氧基的(甲基)丙烯酸酯化合物,从反应性、硬化性的观点来看,较优选为含有缩水甘油基的(甲基)丙烯酸酯单体。
于本发明中,于使前述脂环族异三聚氰酸酯型聚异氰酸酯(a1)与脂环族三羧酸酐(a2)进行反应而得到本发明所使用的聚酰胺酰亚胺树脂(a3)的反应(以下也记载为酰胺酰亚胺化反应)中,较优选为无溶剂或是使用不具有羟基的酯系、不具有羟基的酮系、不具有羟基的醚系等有机溶剂,具有羟基的醇系溶剂会与异氰酸酯或酸酐进行反应,故不优选。不具有羟基的酯系的溶剂可列举例如乙酸乙酯、乙酸丙酯及乙酸丁酯等。不具有羟基的酮系的溶剂可列举例如:丙酮、丁酮、甲基异丁酮、环戊酮及环己酮等。当中,不具有羟基的醚系溶剂可列举:乙二醇二甲醚、乙二醇二乙醚、乙二醇二丁醚等乙二醇二烷醚类;二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇二丁醚、三乙二醇二甲醚、三乙二醇二乙醚、三乙二醇二丁醚等聚乙二醇二烷醚类;乙二醇单甲醚乙酸酯、乙二醇单乙醚乙酸酯、乙二醇单丁醚乙酸酯等乙二醇单烷醚乙酸酯类;二乙二醇单甲醚乙酸酯、二乙二醇单乙醚乙酸酯、二乙二醇单丁醚乙酸酯、三乙二醇单甲醚乙酸酯、三乙二醇单乙醚乙酸酯、三乙二醇单丁醚乙酸酯等聚乙二醇单烷醚乙酸酯类;丙二醇二甲醚、丙二醇二乙醚、丙二醇二丁醚等丙二醇二烷醚类;二丙二醇二甲醚、二丙二醇二乙醚、二丙二醇二丁醚、三丙二醇二甲醚、三丙二醇二乙醚、三丙二醇二丁醚等聚丙二醇二烷醚类;丙二醇单甲醚乙酸酯、丙二醇单乙醚乙酸酯、丙二醇单丁醚乙酸酯等丙二醇单烷醚乙酸酯类;二丙二醇单甲醚乙酸酯、二丙二醇单乙醚乙酸酯、二丙二醇单丁醚乙酸酯、三丙二醇单甲醚乙酸酯、三丙二醇单乙醚乙酸酯、三丙二醇单丁醚乙酸酯等聚丙二醇单烷醚乙酸酯类;或是如低分子的乙烯-丙烯共聚物般的共聚合聚醚二醇的二烷醚,或共聚合聚醚二醇的单乙酸酯单烷醚类;或是如此的聚醚二醇的烷酯类;聚醚二醇的单烷酯单烷醚类等。
前述酰胺酰亚胺化反应较优选为在溶剂中或无溶剂中,混合前述脂环族异三聚氰酸酯型聚异氰酸酯(a1)的1种以上与前述脂环族三羧酸酐(a2)的1种以上,并一面搅拌一面升温来进行。
前述酰胺酰亚胺化反应的反应温度较优选为位于50℃至250℃的范围,特优选位于70℃至180℃的范围。通过设成为此反应温度,具有反应速度增快的效果。反应为一面伴随着脱碳酸,一面让酐基与异氰酸酯基形成酰亚胺基,让羧酸基与异氰酸酯形成酰胺基。于反应时,可任选使用抗氧化剂、整平剂、消泡剂、界面活性剂等。
前述酰胺酰亚胺化反应的进行可通过红外光谱,或是酸值、凝胶渗透层析、液相层析、气相层析、H-NMR、C-NMR、异氰酸酯基的定量等分析方法来追踨。于红外光谱中,作为异氰酸酯基的特性吸收的2250cm-1随着反应的进行而减少,并且于1860cm-1与850cm-1具有特性吸收的酸酐基减少。另一方面,酰亚胺基的吸收于1780cm-1与1720cm-1增加。进行反应直到作为异氰酸酯基的特性吸收的2250cm-1消失为止,容易控制反应,故较优选。
于一分子中具有环氧基的(甲基)丙烯酸酯化合物(b)与前述末端具有酸基或酸酐基的聚酰胺酰亚胺树脂(a3)的反应,较优选为在前述有机溶剂中或无溶剂中进行。
于反应时为了抑制热聚合反应,较优选为加入热聚合抑制剂,其相对于在聚酰胺酰亚胺树脂(a3)中加入了于一分子中具有环氧基的(甲基)丙烯酸酯化合物(b)与溶剂的反应物的总量100质量份,为0.001至1质量份。热聚合抑制剂可列举:对苯二酚、2-甲基对苯二酚、对苯二酚单甲醚、2,6-二(叔丁基)对甲酚等。
此外,于反应时为了促进反应,较优选为使用催化剂,相对于在聚酰胺酰亚胺树脂(a3)中加入了于一分子中具有环氧基的(甲基)丙烯酸酯化合物(b)与溶剂的反应物的总量100质量份,该催化剂的用量为0.001至1质量份。此时的反应温度为60至150℃,此外,反应时间较优选为3至60小时。此反应中所使用的催化剂可列举例如:二甲基胺基吡啶、三乙胺、苄基二甲胺、氯化三乙铵、溴化苄基三甲铵、碘化苄基三甲铵、三苯基膦、三苯基锑化氢、甲基三苯基锑化氢、2-乙基己酸铬、辛酸铬、2-乙基己酸锌、辛酸锌、辛酸锆、二甲硫醚、硫化二苯等。
反应的进行可通过红外光谱,或是酸值、凝胶渗透层析、液相层析、气相层析、H-NMR、C-NMR、环氧基的定量等分析方法来追踨。就保存稳定性的观点而言,以从环氧当量所换算的环氧基的消耗量为95%以上时停止反应为优选。
此外,从硬度或硬化性的观点来看,以前述于一分子中具有环氧基的(甲基)丙烯酸酯(b)与前述脂环族三羧酸酐(a2)的摩尔比((b)/(a2))为0.8至2.0为优选。尤优选为0.9至1.80,更优选为1.0至1.5。于((b)/(a2))为0.8至2.0时,得到硬化性、硬度、胶粘性优异的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A)。另一方面,于((b)/(a2))未达0.8的情形时,硬化性或硬度容易降低,((b)/(a2))大于2.0的情形时,硬度或胶粘性容易降低。
从硬度或硬化性的观点来看,于本发明的活性能量线硬化树脂组合物中,相对于排除了溶剂等的组合物中的固体分量100质量份,以前述聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A)为50至100质量份尤优选。
此外,可任选来使用光聚合引发剂(B)。相对于树脂组合物总量100质量份,光聚合引发剂的用量可使用0.01至10质量份。光聚合引发剂(B)的具体例可列举例如:安息香(Benzoin)、安息香甲醚、安息香乙醚、安息香丙醚、安息香异丁醚等安息香类;苯乙酮(Acetophenone)、2,2-二乙氧基-2-苯基苯乙酮、2,2-二乙氧基-2-苯基苯乙酮、1,1-二氯苯乙酮、2-羟基-2-甲基-苯基丙烷-1-酮、二乙氧基苯乙酮、1-羟基环己基苯基酮、2-甲基-1-[4-(甲硫基)苯基]-2-吗啉基丙烷-1-酮等苯乙酮类;2-乙基蒽醌(2-ethylAnthraquinone)、2-叔丁基蒽醌、2-氯蒽醌、2-戊基蒽醌等蒽醌类;2,4-二乙基噻吨酮(2,4-diethyl Thioxanthone)、2-异丙基噻吨酮、2-氯噻吨酮等噻吨酮类;苯乙酮二甲基缩酮、苄基二甲基缩酮等缩酮类;二苯基酮(Benzophenone)、4-苄酰基-4'-甲基二苯基硫化物、4,4'-双甲基胺基二苯基酮等二苯基酮类;2,4,6-三甲基苄酰基二苯基膦氧化物、双(2,4,6-三甲基苄酰基)-苯基膦氧化物等膦氧化物类等。
于本发明的活性能量线硬化树脂组合物中,可任选来使用有机溶剂(C)。具体而言,前期除了酯系溶剂、酮系溶剂、醚系溶剂之外,也可使用:乙醇、异丙醇、酚般的醇类或酚类;2-乙氧基乙醇、1-甲氧基-2-丙醇般的烷氧醇类;二乙二醇、三丙二醇般的二醇低聚物类;2-乙氧基乙基乙酸酯般的烷氧醇酯类水溶性有机溶剂。
此外,于本发明的活性能量线硬化树脂组合物中,从硬化性或塑化性、溶剂相溶性的观点来看,可使用光聚合性单体(D)。光聚合性单体(D)不包含聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A)。相对于排除了溶剂等的组合物中的固体分量100质量份,光聚合性单体(D)可使用0至50质量份。
前述聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A)以外的光聚合性单体(D),包含通过紫外线或热等所硬化而生成树脂的单体或低聚物,这些可单独或是混合2种以上而使用。
前述光聚合性单体(D)可列举例如单官能(甲基)丙烯酸酯类、多官能(甲基)丙烯酸酯等。
该单官能(甲基)丙烯酸酯类可列举例如:(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸异丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸苯酯、(甲基)丙烯酸联苯酯、(甲基)丙烯酸甲氧基乙酯、(甲基)丙烯酸乙氧基乙酯、(甲基)丙烯酸丁氧基乙二醇酯、(甲基)丙烯酸2-乙基己基乙二醇酯、(甲基)丙烯酸甲氧基丙二醇酯、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸联苯氧基乙酯、(甲基)丙烯酸二环戊烯酯、(甲基)丙烯酸三环癸酯、(甲基)丙烯酸二环戊烯氧基乙酯、(甲基)丙烯酸三环癸氧基乙酯、(甲基)丙烯酸壬基苯氧基乙二醇酯、壬基苯氧基丙二醇、(甲基)丙烯酸苄酯、(甲基)丙烯酸2-羟基乙酯等(甲基)丙烯酸酯类;(甲基)丙烯酰基吗啉((甲基)丙烯酸吗啉酯);(甲基)丙烯酰胺、N-甲基(甲基)丙烯酰胺、N-异丙基(甲基)丙烯酰胺、N-丁基(甲基)丙烯酰胺、N-异丁基(甲基)丙烯酰胺、N-叔丁基(甲基)丙烯酰胺、N-叔辛基(甲基)丙烯酰胺、二丙酮(甲基)丙烯酰胺、N-羟基甲基(甲基)丙烯酰胺、N-羟基乙基(甲基)丙烯酰胺、N-环己基(甲基)丙烯酰胺、N-苯基(甲基)丙烯酰胺、N-苄基(甲基)丙烯酰胺、N-三苯基甲基(甲基)丙烯酰胺、N,N-二甲基(甲基)丙烯酰胺等(甲基)丙烯酰胺类;苯乙烯、乙烯基甲苯、α-甲基苯乙烯等芳香族乙烯基化合物;丁二烯、异戊二烯等丁二烯或取代丁二烯化合物;乙烯、丙烯、氯乙烯、丙烯腈等乙烯或取代乙烯化合物;乙酸乙烯酯等乙烯酯类等单体。
该多官能(甲基)丙烯酸酯类可列举例如:丁二醇二(甲基)丙烯酸酯、己二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、壬二醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、异三聚氰酸三(甲基)丙烯酰氧乙酯、聚丙二醇二(甲基)丙烯酸酯、二(甲基)丙烯酸己二酸环氧酯、双酚环氧乙烷二(甲基)丙烯酸酯、氢化双酚环氧乙烷二(甲基)丙烯酸酯、双酚二(甲基)丙烯酸酯、羟基三甲基乙酸新戊二醇的ε-己内酯加成物的二(甲基)丙烯酸酯、二季戊四醇与ε-己内酯的反应物的聚(甲基)丙烯酸酯、聚(甲基)丙烯酸二季戊四醇酯、三(甲基)丙烯酸三羟甲基丙烷酯、三(甲基)丙烯酸三羟乙基丙烷酯或其环氧乙烷加成物、三(甲基)丙烯酸季戊四醇酯或其环氧乙烷加成物、四(甲基)丙烯酸季戊四醇酯或其环氧乙烷加成物、六(甲基)丙烯酸二季戊四醇酯或其环氧乙烷加成物等。
另外,也可以提高组合物的各项性能为目的来添加任选的各种添加剂,例如:滑石、硫酸钡、碳酸钙、碳酸镁、钛酸钡、氢氧化铝、氧化铝、二氧化硅、粘土等填充剂;纳米二氧化硅等流变减粘性赋予剂;邻苯二甲酸、己二酸、琥珀酸、磷酸、偏苯三酸(TrimelliticAcid)等羧酸系或其酯类等的塑化剂;聚硅氧、氟系等整平剂、消泡剂或抗带电剂;选自由钛、锌、锆、锑、铟、锡、硅、及铝所成组的导电性金属氧化物;酞菁蓝、酞菁绿、炭黑、氧化钛等着色剂;对苯二酚、对苯二酚单甲醚等聚合抑制剂等。
本发明的硬化物为通过紫外线、电子束等能量线的照射使上述本发明的树脂组合物硬化而成。通过紫外线等能量线的照射所进行的硬化,可通过常用方法来进行。例如于照射紫外线的情形时,可使用低压汞灯、高压汞灯、超高压汞灯、氙灯、紫外线发光激光(准分子激光等)等紫外线产生装置。
由于本发明的聚酰胺酰亚胺(甲基)丙烯酸酯树脂的胶粘性、硬度、硬化收缩性、耐湿热性优异,所以适合使用在粘合剂树脂、交联剂、硬涂材料。本发明的硬化物的用途可列举汽车、电脑、显示器等家电制品、移动电话等可携式机器等。
[实施例]
以下通过实施例来更具体地说明本发明,但本发明并不限定于下述实施例。
制造例1
于具备搅拌装置、温度计及冷凝器、氮气管线的四颈烧瓶中,加入甲基异丁酮287.2g与异佛尔酮二异氰酸酯的异三聚氰酸酯变性体(EVONIK公司制“VESTANATT-1890/100”、异氰酸酯基含量17.3质量%)242.8g、以及环己烷-1,3,4-三羧酸-3,4-酐188.1g(0.95mol)。一面将氮气吹送至系统中一面升温至116℃,并在同一温度下进行30小时的反应。通过红外光谱来确认作为异氰酸酯基的特性吸收的2250cm-1的吸收已完全地消失。如此得到通过以聚苯乙烯为标准的凝胶渗透层析所测得的数均分子量为1251、重均分子量为3680的固体分酸值为160mgKOH/g的酰胺酰亚胺树脂中间体(1)溶液。冷却至60℃,加入甲基异丁酮332.5g与甲基丙烯酸缩水甘油酯184.6g(1.30mol)、二丁基羟基甲苯1.7g并搅拌一阵子后,加入三苯基膦1.7g并升温至116℃。于同一温度下进行10小时的反应,而得到固体分酸值为12mgKOH/g、通过凝胶渗透层析所测得的数均分子量为2027、重均分子量为5520的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(I)。
制造例2
于具备搅拌装置、温度计及冷凝器、氮气管线的四颈烧瓶中,加入甲基异丁酮411.1g与异佛尔酮二异氰酸酯的异三聚氰酸酯变性体(EVONIK公司制“VESTANATT-1890/100”、异氰酸酯基含量17.3质量%)242.8g、以及环己烷-1,3,4-三羧酸-3,4-酐168.2g(0.85mol)。一面将氮气吹送至系统中一面升温至116℃,并在同一温度下进行30小时的反应。通过红外光谱来确认作为异氰酸酯基的特性吸收的2250cm-1的吸收已完全地消失。如此得到通过以聚苯乙烯为标准的凝胶渗透层析所测得的数均分子量为1420、重均分子量为4120且固体分酸值为120mgKOH/g的酰胺酰亚胺树脂中间体(1)溶液。冷却至60℃,加入甲基异丁酮188.8g与甲基丙烯酸缩水甘油酯168.3g(0.95mol)、二丁基羟基甲苯1.7g并搅拌一阵子后,加入三苯基膦1.7g并升温至116℃。于同一温度下进行14小时的反应,而得到固体分酸值为35mgKOH/g、通过凝胶渗透层析所测得的数均分子量为2250、重均分子量为6840的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(II)。
制造例3
于具备搅拌装置、温度计及冷凝器、氮气管线的四颈烧瓶中,加入甲基异丁酮124.5g与异佛尔酮二异氰酸酯的异三聚氰酸酯变性体(EVONIK公司制“VESTANATT-1890/100”、异氰酸酯基含量17.3质量%)65.6g、以及环己烷-1,3,4-三羧酸-3,4-酐58.8g(0.3mol)。一面将氮气吹送至系统中一面升温至116℃,并在同一温度下进行24小时的反应。通过红外光谱来确认作为异氰酸酯基的特性吸收的2250cm-1的吸收已完全地消失。如此得到通过以聚苯乙烯为标准的凝胶渗透层析所测得的数均分子量为1170、重均分子量为3520且固体分酸值为170mgKOH/g的酰胺酰亚胺树脂中间体(1)溶液。冷却至60℃,加入甲基异丁酮75.5g与甲基丙烯酸3,4-环氧环己基甲酯74.2g(0.4mol)、二丁基羟基甲苯0.2g并搅拌一阵子后,加入三苯基膦0.2g并升温至116℃。于同一温度下进行14小时的反应,而得到固体分酸值为20mgKOH/g、通过凝胶渗透层析所测得的数均分子量为1820、重均分子量为4440的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(III)。
制造例4
于制造例1中所得到的酰胺酰亚胺树脂中间体(1)中,加入甲基异丁酮203.8g与甲基丙烯酸缩水甘油酯56.8g(0.4mol)、二丁基羟基甲苯1.4g并搅拌一阵子后,加入三苯基膦1.4g并升温至116℃。于同一温度下进行10小时的反应,而得到固体分酸值为142mgKOH/g、通过凝胶渗透层析所测得的数均分子量为1560、重均分子量为4050的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(IV)。
制造例5
于制造例1中所得到的酰胺酰亚胺树脂中间体中,加入甲基异丁酮179.1g与丙烯酸4-羟基丁酯36g(0.25mol)、二丁基羟基甲苯1.2g并搅拌一阵子后,升温至100℃。于同一温度下进行5小时的反应,而得到固体分酸值为175mgKOH/g、通过凝胶渗透层析所测得的数均分子量为1265、重均分子量为3750的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(V)。
树脂组合物的调配及试验用膜的制作
以表1所示的组成来调配制造例1至5中所得到的聚酰胺酰亚胺(甲基)丙烯酸酯树脂,并构成为实施例及比较例。
[表1]
实施例1 | 实施例2 | 实施例3 | 实施例4 | 比较例1 | 比较例2 | 比较例3 | 比较例4 | |
聚酰胺酰亚胺树脂(I) | 100 | 100 | ||||||
聚酰胺酰亚胺树脂(II) | 100 | |||||||
聚酰胺酰亚胺树脂(III) | 100 | |||||||
聚酰胺酰亚胺树脂(IV) | 100 | |||||||
聚酰胺酰亚胺树脂(V) | 100 | |||||||
KAYARAD DPHA | 80 | |||||||
KAYARAD R-115F | 80 | |||||||
NOAA | 15 | 10 | 15 | 15 | 20 | 20 | ||
Light Acrylate S-A | 10 | 5 | ||||||
Omnirad 184 | 1.5 | 1.5 | 1.5 | 1.5 | 1.5 | 1.5 | 2.4 | 2.4 |
BYK307 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.08 | 0.08 |
MIBK | 210 | 190 | 190 | 170 | 210 | 210 | 400 | 400 |
KAYARAD DPHA:二季戊四醇六丙烯酸酯(日本化药公司制)
KAYARAD R-115:BisA型丙烯酸环氧酯(日本化药公司制)
NOAA:丙烯酸正辛酯(大阪有机化学工业公司制)
Light Acrylate S-A:丙烯酸硬脂酯(共荣社化学公司制)
Omnirad 184:α-羟基烷基苯酮(IGMresins公司制)
BYK 307:聚醚变性聚二甲基硅氧烷(BYK Chemie Japan公司制)
MIBK:甲基异丁酮
以下详细说明各评估项目。
(胶粘性)
使用棒涂布机No.16将构成为固体分浓度20%的树脂组合物涂布于易接着聚酯膜(东洋纺股份有限公司制:A-4300膜厚100μm),于105℃的烘箱中干燥2分钟。以手指来接触干燥后的涂覆膜涂膜,并通过下述基准来进行评估。
评估:无胶粘感:〇
树脂附着于手指或是涂膜产生变形:×
干燥后,通过输送带式UV曝光机,以300mJ/cm2进行照射而得到具有硬化覆膜(5μm)的涂覆膜。
(铅笔硬度)
通过输送带式UV曝光机,以300mJ/cm2照射干燥后的涂膜而得到具有硬化覆膜(5μm)的涂覆膜。依循JIS K 5400,使用铅笔刮笔来测定涂覆膜的铅笔硬度。也就是在具有所测定的硬化覆膜的聚酯膜上,以45度的角度将铅笔从上方施加1kg的荷重来进行约5mm的刮痕测试,并确认未产生损伤的铅笔的硬度。
(硬化收缩)
将具有所测定的硬化覆膜的聚酯膜裁切为6cm×6cm,并在80℃的干燥炉中放置1小时后返回室温。然后测定在水平台上所浮起的4边的各高度,以合计值未达10mm为〇,10mm以上且未达20mm为△,20mm以上为×。此时基材本身的卷曲为0mm。
(耐湿热性)
将涂覆膜静置在60℃、90RH%环境下的湿热烘箱中200小时,
然后确认是否产生剥离、白化、龟裂。
评估:无异常:〇
有剥离或是白化:×
实施例1 | 实施例2 | 实施例3 | 实施例4 | 比较例1 | 比较例2 | 比较例3 | 比较例4 | |
胶粘性 | ○ | ○ | ○ | ○ | ○ | ○ | △ | ○ |
硬化收缩 | ○ | ○ | ○ | ○ | ○ | ○ | × | × |
硬度 | 2H | 2H | 3H | 3H | H | B | 2H | HB |
耐湿热性 | ○ | ○ | ○ | ○ | × | × | ○ | ○ |
从上述表2的结果中,可得知本发明的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A)及其组合物的胶粘性、硬度、硬化收缩性、耐湿热性优异。因此适合使用在粘合剂树脂、交联剂、硬涂材料。
Claims (6)
1.一种聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A),使于一分子中具有环氧基的(甲基)丙烯酸酯化合物(b)与末端具有酸基或酸酐基的聚酰胺酰亚胺树脂(a3)反应而得,前述末端具有酸基或酸酐基的聚酰胺酰亚胺树脂(a3)为通过脂环族异三聚氰酸酯型聚异氰酸酯(a1)与脂环族三羧酸酐(a2)的反应而得到。
2.根据权利要求1所述的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A),其中前述含有环氧基之的甲基丙烯酸酯化合物(b)与前述脂环族三羧酸酐(a2)的摩尔比((b)/(a2))为0.8至2.0。
3.一种活性能量线硬化型树脂组合物,含有:权利要求1或2所述的聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A)、光聚合引发剂(B)以及有机溶剂(C)。
4.根据权利要求3所述的活性能量线硬化型树脂组合物,其中含有前述聚酰胺酰亚胺(甲基)丙烯酸酯树脂(A)以外的光聚合性单体(D)。
5.根据权利要求3或4所述的活性能量线硬化型树脂组合物,其为硬涂材料用活性能量线硬化型树脂组合物。
6.一种硬化物,为权利要求3至5中任一项所述的活性能量线硬化型树脂组合物的硬化物。
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