TW202334270A - 聚醯胺醯亞胺(甲基)丙烯酸酯樹脂、使用其之活性能量線硬化型樹脂組成物及其硬化物 - Google Patents
聚醯胺醯亞胺(甲基)丙烯酸酯樹脂、使用其之活性能量線硬化型樹脂組成物及其硬化物 Download PDFInfo
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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
-
- 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
本發明之目的在於,提供一種膠黏性、硬度、硬化收縮性、耐濕熱性優異之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂者。
本發明提供一種聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A),係使於一分子中具有環氧基之(甲基)丙烯酸酯化合物(b),反應於藉由脂環族異三聚氰酸酯型聚異氰酸酯(a1)與脂環族三羧酸酐(a2)之反應所得到之末端具有酸基或酸酐基的聚醯胺醯亞胺樹脂(a3)而得。
Description
本發明係關於聚醯胺醯亞胺(甲基)丙烯酸酯樹脂及使用該聚醯胺醯亞胺(甲基)丙烯酸酯樹脂之活性能量線硬化型樹脂組成物。本發明之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂係適合使用在黏合劑樹脂、交聯劑、硬塗材料。
藉由紫外線或電子束等活性能量線的照射來構成形成交聯結構並硬化之組成物等者,係有其重要性,該技術被使用在住宅建設領域、土木及建築領域、電氣電子及資訊領域、運輸領域等之複合材料基質、注模材料、印墨、塗覆劑、塗料、接著劑等各種用途,產業上極為有用。於此硬化型樹脂組成物中,藉由使用具備複數個具有反應性之官能基的化合物,於硬化後形成交聯結構,玻璃轉移點(Tg)提高,可得到耐熱性或耐溶劑性等物性優異之硬化物。
自以往以來,(甲基)丙烯酸酯寡聚物或(甲基)丙烯酸酯單體係被廣泛地使用作為硬化型樹脂,尤其以提升硬化後之被膜的柔軟性或彈性模數者為目的,係已積極地進行(甲基)丙烯酸環氧酯或胺基甲酸(甲基)丙烯酸酯的開發。
例如於專利文獻1中,係記載有使用了(甲基)丙烯酸酯寡聚物或(甲基)丙烯酸酯單體之硬化性樹脂相對於基材之密著性、透明性、硬化性優異之內容,惟此等硬化性樹脂在硬化時的硬化收縮大,存在有從基材之剝離或硬化物的變形等課題。於專利文獻2中,係記載有使用了胺基甲酸(甲基)丙烯酸酯等之硬化性樹脂,其於柔軟性或是硬化收縮的抑制而言為優異之內容,惟硬度或耐濕熱性仍存在有課題。於專利文獻3中,係揭示有使用了醯胺醯亞胺(甲基)丙烯酸酯等之硬化樹脂,其溶劑溶解性或耐熱性優異之內容,惟耐濕熱性仍存在有課題。
[先前技術文獻]
[專利文獻]
[專利文獻1]日本特開2012-144641號公報
[專利文獻2]日本特許第2964267號公報
[專利文獻3]日本特許第6669311號公報
本發明係鑑於上述現狀,以提供一種膠黏性、硬度、硬化收縮性、耐濕熱性優異之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂者為目的。
本發明人等係進行精心探討,結果發現:使於一分子中具有環氧基之(甲基)丙烯酸酯化合物(b),反應於藉由脂環族異三聚氰酸酯型聚異氰酸酯
(a1)與脂環族三羧酸酐(a2)之反應所得到之末端具有酸基或酸酐基的聚醯胺醯亞胺樹脂(a3)而得之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A),可提供一種乾燥後的膠黏性優異,能夠藉由活性能量線的照射而硬化,並且硬化後的硬度、硬化收縮性、耐濕熱性達到良好之硬化性組成物,因而完成本發明。
亦即,本發明係關於下述[1]至[5]。
[1]一種聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A),係使於一分子中具有環氧基之(甲基)丙烯酸酯化合物(b),反應於藉由脂環族異三聚氰酸酯型聚異氰酸酯(a1)與脂環族三羧酸酐(a2)之反應所得到之末端具有酸基或酸酐基的聚醯胺醯亞胺樹脂(a3)而得。
[2]如[1]所述之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A),其中前述含有環氧基之甲基丙烯酸酯化合物(b)與前述脂環族三羧酸酐(a2)之莫耳比((b)/(a2))為0.8至2.0。
[3]一種活性能量線硬化型樹脂組成物,係含有:如[1]或[2]所述之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A)、光聚合起始劑(B)以及有機溶劑(C)。
[4]如[3]所述之活性能量線硬化型樹脂組成物,其係含有前述聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A)以外的光聚合性單體(D)。
[5]如[3]或[4]所述之活性能量線硬化型樹脂組成物,其係硬塗材料用活性能量線硬化型樹脂組成物。
[6]一種硬化物,係[3]至[5]中任一項所述之活性能量線硬化型樹脂組成物的硬化物。
根據本發明,可提供一種硬度、低硬化收縮性、耐濕熱性優異之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂。
以下係詳細地說明用以實施本發明之型態(以下稱為「本實施型態」)。以下的本實施型態為用以說明本發明之例示,並非將本發明限定於下列內容之意。本發明於該主旨的範圍內,可適當地變形來實施。
本發明係關於一種聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A),係使於一分子中具有環氧基之(甲基)丙烯酸酯化合物(b),反應於藉由脂環族異三聚氰酸酯型聚異氰酸酯(a1)與脂環族三羧酸酐(a2)之反應所得到之末端具有酸基或酸酐基的聚醯胺醯亞胺樹脂(a3)而得。
前述脂環族異三聚氰酸酯型聚異氰酸酯(a1)係在三聚化觸媒存在下或非存在下,將含有脂環族二異氰酸酯化合物之二異氰酸酯化合物進行異三聚氰酸酯化而得到。
於本說明書中所謂脂環族,在本發明的上下文中,意指碳原子配置於環中之化合物(正如將「脂肪族」及「環狀」的2個用語併述而暗示的內容所述)。因此,所謂脂環族,亦為環狀脂肪族的同義詞。結果而言,脂環族化合物係屬於同素環化合物群,在此情形時係包含環烷、環烯及環炔。芳香族化合物及雜環化合物以及雜環化合物的飽和化合物例,在本發明之涵義的範圍內並不被視為脂環族。
前述含有脂環族二異氰酸酯化合物之二異氰酸酯化合物可列舉例如:異佛爾酮二異氰酸酯、氫化甲苯二異氰酸酯、氫化二甲苯二異氰酸酯、降莰烷二異氰酸酯、氫化二苯基甲烷二異氰酸酯等。
前述三聚化觸媒並無特別指定,可列舉例如:2,4,6-參(二甲基胺基甲基)酚、2,4-雙(二甲基胺基甲基)酚、2,4,6-參(二烷基胺基烷基)六氫-S-三等胺化合物;乙酸鉀、2-乙基己酸鉀、辛酸鉀般之碳數2至12之羧酸的鹼金屬鹽;羧酸的4級銨鹽等。市售品可列舉:DABCO P15(Sankyo Film Air Products公司製)、DABCO K15(Sankyo Film Air Products公司製)、PELCAT 9540(Perlon公司製)、DABCO TMR(Sankyo Film Air Products公司製)、TOYOCAT TR20(Tosoh公司製)、U-CAT 18X(Sun Apro公司製)等。
前述脂環族異三聚氰酸酯型聚異氰酸酯(a1)可列舉例如:從異佛爾酮二異氰酸酯所合成之脂環族異三聚氰酸酯型三異氰酸酯(包含五聚體等聚合物)、從氫化甲苯二異氰酸酯所合成之脂環族異三聚氰酸酯型三異氰酸酯(包含五聚體等聚合物)、從氫化二甲苯二異氰酸酯所合成之脂環族異三聚氰酸酯型三異氰酸酯(包含五聚體等聚合物)、從降莰烷二異氰酸酯所合成之異三聚氰酸酯型三異氰酸酯(包含五聚體等聚合物)、從氫化二苯基甲烷二異氰酸酯所合成之脂環族異三聚氰酸酯型三異氰酸酯(包含五聚體等聚合物)等。當中較佳為從異佛爾酮二異氰酸酯所合成之脂環族異三聚氰酸酯型異氰酸酯。藉由使用前述脂環族異三聚氰酸酯型聚異氰酸酯(a1),得到膠黏性或硬化收縮優異之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A)。
前述脂環族三羧酸酐(a2)可列舉環己烷-1,3,4-三羧酸-3,4-酐、環己烷-1,3,5-三羧酸-3,5-酐、環己烷-1,2,3-三羧酸-2,3-酐等。當中較佳為環己烷-
1,3,4-三羧酸-3,4-酐。藉由使用前述脂環族三羧酸酐(a2),得到膠黏性或硬化收縮優異之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A)。
前述脂環族異三聚氰酸酯型聚異氰酸酯(a1)與前述脂環族三羧酸酐(a2)之反應中,相對於前述脂環族異三聚氰酸酯型聚異氰酸酯(a1)所具有之異氰酸酯基1mol,酸酐基與羧酸之合計較佳係設成為1mol以上,尤佳為1.2mol以上,更佳為1.4mol以上。以1.4mol以上來使用時,末端具有酸基或酸酐基的聚醯胺醯亞胺樹脂(a3)係具有所得到之硬化物的硬度或膠黏性優異之效果。此可考量為以1.4mol以上來使用時,由於實質上不含胺基甲酸酯鍵,所以容易控制反應之故。
前述於一分子中具有環氧基之(甲基)丙烯酸酯化合物(b),只要是於分子結構中具有(甲基)丙烯醯基與環氧基者,其他具體的結構就無特別限定,可使用各式各樣的化合物。其一例可列舉例如:縮水甘油(甲基)丙烯酸酯、(甲基)丙烯酸4-羥基丁酯縮水甘油醚、(甲基)丙烯酸環氧環己基甲酯等含有縮水甘油基之(甲基)丙烯酸酯單體;二羥基苯二縮水甘油醚、二羥基萘二縮水甘油醚、聯苯酚二縮水甘油醚、雙酚二縮水甘油醚等二縮水甘油醚化合物的單(甲基)丙烯酸酯化合物等。此等具有環氧基的(甲基)丙烯酸酯化合物可單獨使用,亦可併用2種以上。此等當中,由於容易控制反應,故較佳為具有1個環氧基之(甲基)丙烯酸酯化合物,從反應性、硬化性之觀點來看,較佳為含有縮水甘油基的(甲基)丙烯酸酯單體。
於本發明中,於使前述脂環族異三聚氰酸酯型聚異氰酸酯(a1)與脂環族三羧酸酐(a2)進行反應而得到本發明所使用之聚醯胺醯亞胺樹脂(a3)之反應(以下亦記載為醯胺醯亞胺化反應)中,較佳為無溶劑或是使用不具有羥基之酯
系、不具有羥基之酮系、不具有羥基之醚系等有機溶劑,具有羥基之醇系溶劑會與異氰酸酯或酸酐進行反應,故不佳。不具有羥基之酯系的溶劑可列舉例如乙酸乙酯、乙酸丙酯及乙酸丁酯等。不具有羥基之酮系的溶劑可列舉例如:丙酮、丁酮、甲基異丁酮、環戊酮及環己酮等。當中,不具有羥基之醚系溶劑可列舉: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類;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類;乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、乙二醇單丁醚乙酸酯等乙二醇單烷醚乙酸酯類;二乙二醇單甲醚乙酸酯、二乙二醇單乙醚乙酸酯、二乙二醇單丁醚乙酸酯、三乙二醇單甲醚乙酸酯、三乙二醇單乙醚乙酸酯、三乙二醇單丁醚乙酸酯等聚乙二醇單烷醚乙酸酯類;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類;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類;丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丁醚乙酸酯等丙二醇單烷醚乙酸酯類;二丙二醇單甲醚乙酸酯、二丙二醇單乙醚乙酸酯、二丙二醇單丁醚乙酸酯、三丙二醇單甲醚乙酸酯、三丙二醇單乙醚乙酸酯、三丙二醇單丁醚乙酸酯等聚丙二醇單烷醚乙酸酯類;或是如低分子的乙烯-丙烯共聚物般之共聚合聚醚二醇的二烷醚,或共聚合聚醚二醇的單乙酸酯單烷醚類;或是如此之聚醚二醇的烷酯類;聚醚二醇的單烷酯單烷醚類等。
前述醯胺醯亞胺化反應較佳係在溶劑中或無溶劑中,混合前述脂環族異三聚氰酸酯型聚異氰酸酯(a1)的1種以上與前述脂環族三羧酸酐(a2)的1種以上,並一面攪拌一面升溫來進行。
前述醯胺醯亞胺化反應的反應溫度較佳係位於50℃至250℃的範圍,特佳位於70℃至180℃的範圍。藉由設成為此反應溫度,係具有反應速度增快之效果。反應係一面伴隨著脫碳酸,一面讓酐基與異氰酸酯基形成醯亞胺基,讓羧酸基與異氰酸酯形成醯胺基。於反應時,可視需要使用抗氧化劑、整平劑、消泡劑、界面活性劑等。
前述醯胺醯亞胺化反應的進行可藉由紅外光譜,或是酸值、凝膠滲透層析、液相層析、氣相層析、H-NMR、C-NMR、異氰酸酯基的定量等分析手段來追踨。於紅外光譜中,作為異氰酸酯基的特性吸收之2250cm-1係隨著反應的進行而減少,並且於1860cm-1與850cm-1具有特性吸收之酸酐基減少。另一方面,醯亞胺基的吸收於1780cm-1與1720cm-1增加。進行反應至作為異氰酸酯基的特性吸收之2250cm-1消失為止者,係容易控制反應,故較佳。
於一分子中具有環氧基之(甲基)丙烯酸酯化合物(b)與前述末端具有酸基或酸酐基的聚醯胺醯亞胺樹脂(a3)之反應,較佳係在前述有機溶劑中或無溶劑中進行。
於反應時為了抑制熱聚合反應,較佳係加入熱聚合抑制劑,其相對於在聚醯胺醯亞胺樹脂(a3)中加入了於一分子中具有環氧基之(甲基)丙烯酸酯化合物(b)與溶劑之反應物的總量100質量份,為0.001至1質量份。熱聚合抑制劑可列舉:對苯二酚、2-甲基對苯二酚、對苯二酚單甲醚、2,6-二(第三丁基)對甲酚等。
此外,於反應時為了促進反應,較佳係使用觸媒,相對於在聚醯胺醯亞胺樹脂(a3)中加入了於一分子中具有環氧基之(甲基)丙烯酸酯化合物(b)與溶劑之反應物的總量100質量份,該觸媒的用量為0.001至1質量份。此時的
反應溫度為60至150℃,此外,反應時間較佳為3至60小時。此反應中所使用之觸媒可列舉例如:二甲基胺基吡啶、三乙胺、苄基二甲胺、氯化三乙銨、溴化苄基三甲銨、碘化苄基三甲銨、三苯基膦、三苯基銻化氫、甲基三苯基銻化氫、2-乙基己酸鉻、辛酸鉻、2-乙基己酸鋅、辛酸鋅、辛酸鋯、二甲硫醚、硫化二苯等。
反應的進行可藉由紅外光譜,或是酸值、凝膠滲透層析、液相層析、氣相層析、H-NMR、C-NMR、環氧基的定量等分析手段來追蹤。從環氧當量所換算之環氧基的消耗量為95%以上時停止反應者,就保存穩定性之觀點而言為佳。
此外,前述於一分子中具有環氧基之(甲基)丙烯酸酯(b)與前述脂環族三羧酸酐(a2)之莫耳比((b)/(a2))為0.8至2.0者,從硬度或硬化性之觀點來看為佳。尤佳為0.9至1.80,更佳為1.0至1.5。於((b)/(a2))為0.8至2.0時,係得到硬化性、硬度、膠黏性優異之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A)。另一方面,於((b)/(a2))未達0.8之情形時,硬化性或硬度容易降低,((b)/(a2))大於2.0之情形時,硬度或膠黏性容易降低。
於本發明之活性能量線硬化樹脂組成物中,相對於排除了溶劑等之組成物中的固形份量100質量份,前述聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A)為50至100質量份者,從硬度或硬化性之觀點來看尤佳。
此外,可視需要來使用光聚合起始劑(B)。相對於樹脂組成物總量100質量份,光聚合起始劑的用量可使用0.01至10質量份。光聚合起始劑(B)的具體例可列舉例如:安息香(Benzoin)、安息香甲醚、安息香乙醚、安息香丙醚、安息香異丁醚等安息香類;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-羥基-2-甲基-苯基丙烷-1-酮、二乙氧基苯乙酮、1-羥基環己基苯基酮、2-甲基-1-[4-(甲硫基)苯基]-2-嗎啉基丙烷-1-酮等苯乙酮類;2-乙基蒽醌(2-ethyl Anthraquinone)、2-第三丁基蒽醌、2-氯蒽醌、2-戊基蒽醌等蒽醌類;2,4-二乙基噻吨酮(2,4-diethyl Thioxanthone)、2-異丙基噻吨酮、2-氯噻吨酮等噻吨酮類;苯乙酮二甲基縮酮、苄基二甲基縮酮等縮酮類;二苯基酮(Benzophenone)、4-苄醯基-4'-甲基二苯基硫化物、4,4'-雙甲基胺基二苯基酮等二苯基酮類;2,4,6-三甲基苄醯基二苯基膦氧化物、雙(2,4,6-三甲基苄醯基)-苯基膦氧化物等膦氧化物類等。
於本發明之活性能量線硬化樹脂組成物中,可視需要來使用有機溶劑(C)。具體而言,前期除了酯系溶劑、酮系溶劑、醚系溶劑之外,亦可使用:乙醇、異丙醇、酚般之醇類或酚類;2-乙氧基乙醇、1-甲氧基-2-丙醇般之烷氧醇類;二乙二醇、三丙二醇般之二醇寡聚物類;2-乙氧基乙基乙酸酯般之烷氧醇酯類水溶性有機溶劑。
此外,於本發明之活性能量線硬化樹脂組成物中,從硬化性或塑化性、溶劑相溶性之觀點來看,可使用光聚合性單體(D)。光聚合性單體(D)不包含聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A)。相對於排除了溶劑等之組成物中的固形份量100質量份,光聚合性單體(D)可使用0至50質量份。
前述聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A)以外的光聚合性單體(D),係包含藉由紫外線或熱等所硬化而生成樹脂之單體或寡聚物,此等可單獨或是混合2種以上而使用。
前述光聚合性單體(D)可列舉例如單官能(甲基)丙烯酸酯類、多官能(甲基)丙烯酸酯等。
該單官能(甲基)丙烯酸酯類可列舉例如:(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸異丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸環己酯、(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)丙烯酸聯苯酯、(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)丙烯酸聯苯氧基乙酯、(甲基)丙烯酸二環戊烯酯、(甲基)丙烯酸三環癸酯、(甲基)丙烯酸二環戊烯氧基乙酯、(甲基)丙烯酸三環癸氧基乙酯、(甲基)丙烯酸壬基苯氧基乙二醇酯、(甲基)丙烯酸壬基苯氧基丙二醇、(甲基)丙烯酸苄酯、(甲基)丙烯酸2-羥基乙酯等(甲基)丙烯酸酯類;(甲基)丙烯醯基嗎啉((甲基)丙烯酸嗎啉酯);(甲基)丙烯醯胺、N-甲基(甲基)丙烯醯胺、N-異丙基(甲基)丙烯醯胺、N-丁基(甲基)丙烯醯胺、N-異丁基(甲基)丙烯醯胺、N-第三丁基(甲基)丙烯醯胺、N-第三辛基(甲基)丙烯醯胺、二丙酮(甲基)丙烯醯胺、N-羥基甲基(甲基)丙烯醯胺、N-羥基乙基(甲基)丙烯醯胺、N-環己基(甲基)丙烯醯胺、N-苯基(甲基)丙烯醯胺、N-苄基(甲基)丙烯醯胺、N-三苯基甲基(甲基)丙烯醯胺、N,N-二甲基(甲基)丙烯醯胺等(甲基)丙烯醯胺類;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、異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類等單體。
該多官能(甲基)丙烯酸酯類可列舉例如: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、異三聚氰酸三(甲基)丙烯醯氧乙酯、聚丙二醇二(甲基)丙烯酸酯、二(甲基)丙烯酸己二酸環氧酯、雙酚環氧乙烷二(甲基)丙烯酸酯、氫化雙酚環氧乙烷二(甲基)丙烯酸酯、雙酚二(甲基)丙烯酸酯、羥基三甲基乙酸新戊二醇的ε-己內酯加成物之二(甲基)丙烯酸酯、二新戊四醇與ε-己內酯的反應物之聚(甲基)丙烯酸酯、聚(甲基)丙烯酸二新戊四醇酯、三(甲基)丙烯酸三羥甲基丙烷酯、三(甲基)丙烯酸三羥乙基丙烷酯或其環氧乙烷加成物、三(甲基)丙烯酸新戊四醇酯或其環氧乙烷加成物、四(甲基)丙烯酸新戊四醇酯或其環氧乙烷加成物、六(甲基)丙烯酸二新戊四醇酯或其環氧乙烷加成物等。
再者,亦可視需要,以提高組成物的各項性能者為目的來添加各種添加劑,例如:滑石、硫酸鋇、碳酸鈣、碳酸鎂、鈦酸鋇、氫氧化鋁、氧化鋁、二氧化矽、黏土等填充劑;奈米二氧化矽等流變減黏性賦予劑;鄰苯二甲酸、己二酸、琥珀酸、磷酸、偏苯三酸(Trimellitic Acid)等羧酸系或其酯類等的塑化劑;聚矽氧、氟系等整平劑、消泡劑或抗帶電劑;選自由鈦、鋅、鋯、銻、銦、錫、矽、及鋁所組成之群組的導電性金屬氧化物;酞菁藍、酞菁綠、碳黑、氧化鈦等著色劑;對苯二酚、對苯二酚單甲醚等聚合抑制劑等。
所謂本發明之硬化物,為藉由紫外線、電子束等能量線的照射而使上述本發明之樹脂組成物硬化者。藉由紫外線等能量線的照射所進行之硬化,可藉由常用方法來進行。例如於照射紫外線之情形時,可使用低壓汞燈、高壓汞燈、超高壓汞燈、氙燈、紫外線發光雷射(準分子雷射等)等紫外線產生裝置。
由於本發明之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂的膠黏性、硬度、硬化收縮性、耐濕熱性優異,所以適合使用在黏合劑樹脂、交聯劑、硬塗材
料。本發明之硬化物的用途可列舉汽車、電腦、顯示器等家電製品、行動電話等可攜式機器等。
[實施例]
以下係藉由實施例來更具體地說明本發明,惟本發明並不限定於下述實施例。
製造例1
於具備攪拌裝置、溫度計及冷凝器、氮氣管線之四頸燒瓶中,加入甲基異丁酮287.2g與異佛爾酮二異氰酸酯的異三聚氰酸酯變性體(EVONIK公司製「VESTANATT-1890/100」、異氰酸酯基含量17.3質量%)242.8g、以及環己烷-1,3,4-三羧酸-3,4-酐188.1g(0.95mol)。一面將氮氣吹送至系統中一面升溫至116℃,並在同一溫度下進行30小時的反應。藉由紅外光譜來確認作為異氰酸酯基的特性吸收之2250cm-1的吸收已完全地消失。如此得到藉由以聚苯乙烯為標準之凝膠滲透層析所測得之數量平均分子量為1251、重量平均分子量為3680之固形份酸值為160mgKOH/g之醯胺醯亞胺樹脂中間體(1)溶液。冷卻至60℃,加入甲基異丁酮332.5g與甲基丙烯酸縮水甘油酯184.6g(1.30mol)、二丁基羥基甲苯1.7g並攪拌一陣子後,加入三苯基膦1.7g並升溫至116℃。於同一溫度下進行10小時的反應,而得到固形份酸值為12mgKOH/g、藉由凝膠滲透層析所測得之數量平均分子量為2027、重量平均分子量為5520之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(I)。
製造例2
於具備攪拌裝置、溫度計及冷凝器、氮氣管線之四頸燒瓶中,加入甲基異丁酮411.1g與異佛爾酮二異氰酸酯的異三聚氰酸酯變性體(EVONIK公司製
「VESTANATT-1890/100」、異氰酸酯基含量17.3質量%)242.8g、以及環己烷-1,3,4-三羧酸-3,4-酐168.2g(0.85mol)。一面將氮氣吹送至系統中一面升溫至116℃,並在同一溫度下進行30小時的反應。藉由紅外光譜來確認作為異氰酸酯基的特性吸收之2250cm-1的吸收已完全地消失。如此得到藉由以聚苯乙烯為標準之凝膠滲透層析所測得之數量平均分子量為1420、重量平均分子量為4120且固形份酸值為120mgKOH/g之醯胺醯亞胺樹脂中間體(1)溶液。冷卻至60℃,加入甲基異丁酮188.8g與甲基丙烯酸縮水甘油酯168.3g(0.95mol)、二丁基羥基甲苯1.7g並攪拌一陣子後,加入三苯基膦1.7g並升溫至116℃。於同一溫度下進行14小時的反應,而得到固形份酸值為35mgKOH/g、藉由凝膠滲透層析所測得之數量平均分子量為2250、重量平均分子量為6840之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(II)。
製造例3
於具備攪拌裝置、溫度計及冷凝器、氮氣管線之四頸燒瓶中,加入甲基異丁酮124.5g與異佛爾酮二異氰酸酯的異三聚氰酸酯變性體(EVONIK公司製「VESTANATT-1890/100」、異氰酸酯基含量17.3質量%)65.6g、以及環己烷-1,3,4-三羧酸-3,4-酐58.8g(0.3mol)。一面將氮氣吹送至系統中一面升溫至116℃,並在同一溫度下進行24小時的反應。藉由紅外光譜來確認作為異氰酸酯基的特性吸收之2250cm-1的吸收已完全地消失。如此得到藉由以聚苯乙烯為標準之凝膠滲透層析所測得之數量平均分子量為1170、重量平均分子量為3520且固形份酸值為170mgKOH/g之醯胺醯亞胺樹脂中間體(1)溶液。冷卻至60℃,加入甲基異丁酮75.5g與甲基丙烯酸3,4-環氧環己基甲酯74.2g(0.4mol)、二丁基羥基甲苯0.2g並攪拌一陣子後,加入三苯基膦0.2g並升溫至116℃。於同一溫度下進行
14小時的反應,而得到固形份酸值為20mgKOH/g、藉由凝膠滲透層析所測得之數量平均分子量為1820、重量平均分子量為4440之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(III)。
製造例4
於製造例1中所得到之醯胺醯亞胺樹脂中間體(1)中,加入甲基異丁酮203.8g與甲基丙烯酸縮水甘油酯56.8g(0.4mol)、二丁基羥基甲苯1.4g並攪拌一陣子後,加入三苯基膦1.4g並升溫至116℃。於同一溫度下進行10小時的反應,而得到固形份酸值為142mgKOH/g、藉由凝膠滲透層析所測得之數量平均分子量為1560、重量平均分子量為4050之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(IV)。
製造例5
於製造例1中所得到之醯胺醯亞胺樹脂中間體中,加入甲基異丁酮179.1g與丙烯酸4-羥基丁酯36g(0.25mol)、二丁基羥基甲苯1.2g並攪拌一陣子後,升溫至100℃。於同一溫度下進行5小時的反應,而得到固形份酸值為175mgKOH/g、藉由凝膠滲透層析所測得之數量平均分子量為1265、重量平均分子量為3750之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(V)。
樹脂組成物的調配及試驗用膜的製作
以表1所示之組成來調配製造例1至5中所得到之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂,並構成為實施例及比較例。
KAYARAD DPHA:二新戊四醇六丙烯酸酯(日本化藥公司製)
KAYARAD R-115:BisA型丙烯酸環氧酯(日本化藥公司製)
NOAA:丙烯酸正辛酯(大阪有機化學工業公司製)
Light Acrylate S-A:丙烯酸硬脂酯(共榮社化學公司製)
Omnirad 184:α-羥基烷基苯酮(IGMresins公司製)
BYK 307:聚醚變性聚二甲基矽氧烷(BYK Chemie Japan公司製)
MIBK:甲基異丁酮
以下詳細說明各評估項目。
(膠黏性)
使用棒塗佈機No.16將構成為固形份濃度20%之樹脂組成物塗佈於易接著聚酯膜(東洋紡股份有限公司製:A-4300膜厚100μm),於105℃的烘箱中乾燥2分鐘。以手指來接觸乾燥後的塗覆膜塗膜,並藉由下述基準來進行評估。
評估:無膠黏感:○
樹脂附著於手指或是塗膜產生變形:×
乾燥後,藉由輸送帶式UV曝光機,以300mJ/cm2進行照射而得到具有硬化覆膜(5μm)之塗覆膜。
(鉛筆硬度)
藉由輸送帶式UV曝光機,以300mJ/cm2照射乾燥後的塗膜而得到具有硬化覆膜(5μm)之塗覆膜。依循JIS K 5400,使用鉛筆刮筆來測定塗覆膜的鉛筆硬度。亦即在具有所測定之硬化覆膜的聚酯膜上,以45度的角度將鉛筆從上方施加1kg的荷重來進行約5mm的刮痕測試,並確認未產生損傷之鉛筆的硬度。
(硬化收縮)
將具有所測定之硬化覆膜的聚酯膜裁切為6cm×6cm,並在80℃的乾燥爐中放置1小時後返回室溫。然後測定在水平台上所浮起之4邊的各高度,以合計值未達10mm者為○,10mm以上且未達20mm者為△,20mm以上者為×。此時基材本身的捲曲為0mm。
(耐濕熱性)
將塗覆膜靜置在60℃、90RH%環境下的濕熱烘箱中200小時,然後確認是否產生剝離、白化、龜裂。
評估:無異常:○
有剝離或是白化:×
從上述表2的結果中,可得知本發明之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A)及其組成物的膠黏性、硬度、硬化收縮性、耐濕熱性優異。因此適合使用在黏合劑樹脂、交聯劑、硬塗材料。
Claims (6)
- 一種聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A),係使於一分子中具有環氧基之(甲基)丙烯酸酯化合物(b),反應於藉由脂環族異三聚氰酸酯型聚異氰酸酯(a1)與脂環族三羧酸酐(a2)之反應所得到之末端具有酸基或酸酐基的聚醯胺醯亞胺樹脂(a3)而得。
- 如請求項1所述之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A),其中前述含有環氧基之甲基丙烯酸酯化合物(b)與前述脂環族三羧酸酐(a2)之莫耳比((b)/(a2))為0.8至2.0。
- 一種活性能量線硬化型樹脂組成物,係含有:請求項1或2所述之聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A)、光聚合起始劑(B)以及有機溶劑(C)。
- 如請求項3所述之活性能量線硬化型樹脂組成物,其係含有前述聚醯胺醯亞胺(甲基)丙烯酸酯樹脂(A)以外的光聚合性單體(D)。
- 如請求項3或4所述之活性能量線硬化型樹脂組成物,其係硬塗材料用活性能量線硬化型樹脂組成物。
- 一種硬化物,係請求項3至5中任一項所述之活性能量線硬化型樹脂組成物的硬化物。
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