TW202212396A - 胺基甲酸酯(甲基)丙烯酸酯、活性能量射線硬化型樹脂組成物、硬化物及積層體 - Google Patents
胺基甲酸酯(甲基)丙烯酸酯、活性能量射線硬化型樹脂組成物、硬化物及積層體 Download PDFInfo
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- TW202212396A TW202212396A TW110123877A TW110123877A TW202212396A TW 202212396 A TW202212396 A TW 202212396A TW 110123877 A TW110123877 A TW 110123877A TW 110123877 A TW110123877 A TW 110123877A TW 202212396 A TW202212396 A TW 202212396A
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- Prior art keywords
- meth
- acrylate
- component
- urethane
- energy ray
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 156
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 239000011342 resin composition Substances 0.000 title claims abstract description 34
- 229920000642 polymer Polymers 0.000 claims abstract description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
- 230000035699 permeability Effects 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000004678 hydrides Chemical class 0.000 claims abstract description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 10
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 10
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 6
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
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- 150000004706 metal oxides Chemical class 0.000 claims description 6
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Classifications
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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
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
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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
- 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
- C08F290/067—Polyurethanes; Polyureas
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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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6204—Polymers of olefins
- C08G18/6208—Hydrogenated polymers of conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
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- C—CHEMISTRY; METALLURGY
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Abstract
本發明係提供一種提供具備低透濕性之硬化物之胺基甲酸酯(甲基)丙烯酸酯、及活性能量射線硬化型樹脂組成物。
該胺基甲酸酯(甲基)丙烯酸酯,係下述聚合物之氫化物(a1)、與下述(I)及/或(II)之反應物;
該聚合物係具有烯烴性雙鍵及環狀結構之烴(a1-1)與具有活性氫之化合物(a1-2)之聚合物;
(I)具有1個異氰酸酯基之(甲基)丙烯酸酯(a2);
(II)多異氰酸酯(a3)及具有羥基之(甲基)丙烯酸酯(a4)。
Description
本發明係關於胺基甲酸酯(甲基)丙烯酸酯、活性能量射線硬化型樹脂組成物、硬化物及積層體。
以往,用於液晶顯示裝置之偏振板,係藉由在使碘等吸附於聚乙烯醇薄膜並藉由拉伸等而定向之偏振片之兩面貼合三乙酸纖維素薄膜(TAC薄膜)來製造。此外,在TAC薄膜之表面,塗布透明的活性能量射線硬化型樹脂組成物,進行硬化而形成高硬度之被膜(硬塗層),而賦予防劃傷功能。如此之樹脂組成物,已知有例如使用多官能胺基甲酸酯(甲基)丙烯酸酯等之物質(專利文獻1)。
然而,TAC薄膜,由於吸濕性高(具有高透濕性),因而根據使用環境的不同,可能會因濕度而伸縮,導致顯示不均等。
作為解決透濕性之技術,已揭示一種必須含有羥值為10mgKOH/g以下之石油樹脂、及(甲基)丙烯酸酯化合物之活性能量射線硬化型樹脂組成物,惟即便使用該石油樹脂,透濕性依然是高的(專利文獻2)。
[先前技術文獻]
[專利文獻]
[專利文獻1]日本特開平9-290491號公報
[專利文獻2]日本特開2018-135452號公報
[發明所欲解決之技術問題]
本發明之課題在於提供一種提供具備低透濕性之硬化物之胺基甲酸酯(甲基)丙烯酸酯、及活性能量射線硬化型樹脂組成物。
[技術手段]
本發明人等進行深入研究,結果發現以特定之烯烴系聚合物之氫化物作為原料而合成之胺基甲酸酯(甲基)丙烯酸酯可解決上述課題,從而完成本發明。即,本發明係關於以下之胺基甲酸酯(甲基)丙烯酸酯、活性能量射線硬化型樹脂組成物、硬化物及積層體。
1. 一種胺基甲酸酯(甲基)丙烯酸酯,其特徵係其為下述聚合物之氫化物(a1)、與下述(I)及/或(II)之反應物;
該聚合物係具有烯烴性雙鍵及環狀結構之烴(a1-1)與具有活性氫之化合物(a1-2)之聚合物;
(I)具有1個異氰酸酯基之(甲基)丙烯酸酯(a2);
(II)多異氰酸酯(a3)及具有羥基之(甲基)丙烯酸酯(a4)。
2. 如前項1所述之胺基甲酸酯(甲基)丙烯酸酯,其中,(a1-1)成分含有雙環戊二烯類及/或苯乙烯類。
3. 如前項1或2所述之胺基甲酸酯(甲基)丙烯酸酯,其中,(a1-2)成分含有不飽和脂肪族醇。
4. 如前項1~3中任一項所述之胺基甲酸酯(甲基)丙烯酸酯,其中,(a2)成分為(甲基)丙烯酸異氰酸基烷酯。
5. 如前項1~4中任一項所述之胺基甲酸酯(甲基)丙烯酸酯,其中,(a3)成分為脂環族多異氰酸酯。
6.一種活性能量射線硬化型樹脂組成物,其特徵係含有如前項1~5中任一項所述之胺基甲酸酯(甲基)丙烯酸酯。
7. 如前項6所述之活性能量射線硬化型樹脂組成物,其中,其進一步含有活性能量射線硬化型單體(B)及/或金屬氧化物(C)。
8.一種硬化物,其特徵係其為如前項6或7所述之活性能量射線硬化型樹脂組成物之硬化物。
9. 一種積層體,其特徵係在透濕度為200g/m
2・24h以上之基材薄膜之至少單面具有如前項8所述之硬化物。
10. 如前項9所述之積層體,其中,其透濕度為100g/m
2・24h以下。
[發明之效果]
本發明之胺基甲酸酯(甲基)丙烯酸酯提供具備低透濕性之硬化物。此外,前述硬化物的耐光性亦優異,亦可維持硬度。該硬化物係低透濕性,因而能夠適用於阻隔膜、偏振板、有機EL元件之密封材、包裝薄膜等用途。
本發明之胺基甲酸酯(甲基)丙烯酸酯係下述聚合物之氫化物(a1)(以下稱為(a1)成分。)、與下述(I)及/或(II)之反應物;該聚合物係具有烯烴性雙鍵及環狀結構之烴(a1-1)(以下稱為(a1-1)成分。)與具有活性氫之化合物(a1-2)(以下稱為(a1-2)成分。)之聚合物;
(I)具有1個異氰酸酯基之(甲基)丙烯酸酯(a2)(以下稱為(a2)成分。)
(II)多異氰酸酯(a3)(以下稱為(a3)成分。)及具有羥基之(甲基)丙烯酸酯(a4)(以下稱為(a4)成分。)。
本發明之胺基甲酸酯(甲基)丙烯酸酯,可列舉例如:(a1)成分與(a2)成分之反應物(以下稱為胺基甲酸酯(甲基)丙烯酸酯(A1)。);或者
(a1)成分、與(a3)成分及(a4)成分之反應物(以下稱為胺基甲酸酯(甲基)丙烯酸酯(A2)。)等。
首先,對胺基甲酸酯(甲基)丙烯酸酯(A1)(以下亦稱為(A1)成分。)進行說明。
(a1)成分係具有烯烴性雙鍵及環狀結構之烴(a1-1)與具有活性氫之化合物(a1-2)之聚合物之氫化物。藉由使用(a1)成分,從而硬化物顯示低透濕性。
(a1-1)成分係由碳原子及氫原子構成、且在分子中具有至少一個烯烴性雙鍵及至少一個環狀結構之烴。(a1-1)成分,沒有特別地限定,可列舉例如:環丁烯、甲基環丁烯、二甲基環丁烯、四甲基環丁烯、乙基環丁烯等環丁烯類;環戊烯、甲基環戊烯、二甲基環戊烯、乙基環戊烯、乙基甲基環戊烯、丙基環戊烯等環戊烯類;環己烯、甲基環己烯、二甲基環己烯、三甲基環己烯、四甲基環己烯、乙基環己烯、乙基甲基環己烯、甲基丙基環己烯、異丙基甲基環己烯、丁基環己烯等環己烯類;環庚烯、甲基環戊烯、二甲基環戊烯、乙基環戊烯、丙基環戊烯等環庚烯類;環辛烯、甲基環辛烯等環辛烯類;環丁二烯、甲基環丁二烯、二甲基環丁二烯、乙基環丁二烯等環丁二烯類;環戊二烯、甲基環戊二烯、二甲基環戊二烯、四甲基環戊二烯、四甲基環戊二烯、五甲基環戊二烯、乙基環戊二烯、二乙基環戊二烯等環戊二烯類;環己二烯、甲基環己二烯、二甲基環己二烯、三甲基環己二烯、四甲基環己二烯、五甲基環己二烯、甲基異丙基環己二烯等環己二烯類;環辛二烯、二甲基環辛二烯等環辛二烯類;雙環戊二烯、甲基雙環戊二烯、二甲基雙環戊二烯、四甲基雙環戊二烯、五甲基雙環戊二烯、乙基雙環戊二烯、二乙基雙環戊二烯等雙環戊二烯類;雙環己二烯、甲基雙環己二烯、二甲基雙環己二烯、三甲基雙環己二烯、四甲基雙環己二烯、五甲基雙環己二烯等雙環己二烯類;苯乙烯、α-甲基苯乙烯、β-甲基苯乙烯、2-甲基苯乙烯、3-甲基苯乙烯、4-甲基苯乙烯、2-乙基苯乙烯、3-乙基苯乙烯、4-乙基苯乙烯等苯乙烯類;茚、甲基茚、二甲基茚、乙基茚、丁基茚等茚類等。此等可為單獨,亦可組合2種以上。其中,從與(a1-2)成分之反應性之觀點而言,理想係含有雙環戊二烯類及/或苯乙烯類。
(a1-2)成分,意指在分子內具有至少1個活性氫之化合物。「活性氫」,意指分子內之羥基(-OH)、羧基(-COOH)、硫醇基(-SH)、磺基(-SO
3H)、胺基(-NH
2、-NH-)、磷酸基(-O-P(=O)-(OH)
2)等官能基中之氫原子,惟在本發明中,從容易與後述之(a2)成分或(a3)成分反應之觀點而言,理想係具有羥基之化合物、具有羧基之化合物、具有胺基之化合物。
具有羥基之化合物,可列舉例如:烯丙醇、甲基烯丙醇等不飽和脂肪族醇;(甲基)丙烯酸2-羥乙酯、(甲基)丙烯酸3-羥丙酯、(甲基)丙烯酸2-羥丁酯、(甲基)丙烯酸3-羥丁酯、(甲基)丙烯酸4-羥丁酯等(甲基)丙烯酸羥基烷酯;苯酚、甲酚、雙酚A、雙酚F、苯酚酚醛清漆等酚系化合物等。此等可為單獨,亦可組合2種以上。又,「不飽和」,意指分子中具有至少1個碳-碳雙鍵及/或碳-碳三鍵(以下相同)。
具有羧基之化合物,可列舉例如:馬來酸、馬來酸酐、富馬酸等不飽和脂肪族羧酸;鄰苯二甲酸、間苯二甲酸、鄰苯二甲酸酐、偏苯三甲酸等芳香族羧酸等。此等可為單獨,亦可組合2種以上。
具有胺基之化合物,可列舉例如:烯丙胺、甲基烯丙胺等不飽和脂肪族胺;苯胺等芳香族胺等。此等可為單獨,亦可組合2種以上。
上述此等之化合物中,從與(a1-1)成分之反應性而言,理想係不飽和脂肪族醇。
(a1-1)成分及(a1-2)成分之使用比率,通常以莫耳比計為3/1~1/3,理想為2/1~1/2。
氫化反應前之聚合物可以藉由使(a1-2)成分與(a1-1)成分共存並發生反應而得到。反應方法,沒有特別地限定,可以採用各種習知之方法。可列舉例如:在氯化鋁或三氟化硼等觸媒之存在下,在-20~60℃左右之條件下,使(a1-1)成分及(a1-2)成分反應1~6小時而使之發生陽離子聚合之方法;在高壓釜中,在150~300℃左右之條件下,將(a1-1)成分及(a1-2)成分加熱1~8小時而使之發生熱聚合之方法等。在前述熱聚合中,可以根據需要而添加二第三丁基過氧化物等自由基產生劑。
前述聚合,亦可以在無溶劑下進行,但從反應時之發熱量之觀點而言,理想係在有機溶劑中進行。有機溶劑,只要是對前述此等反應成分呈惰性之物質,則沒有特別地限定,可列舉例如:環己烷、甲基環己烷、乙基環己烷等脂環族烴;苯、甲苯、二甲苯等芳香族烴等。此等可為單獨,亦可組合2種以上。此外,有機溶劑之使用量,理想調整為以反應濃度計為20~95重量%、理想為40~90重量%。
(a1)成分係將前述所得之聚合物氫化後之物質。氫化條件,通常,壓力為1~30MPa左右(理想為3~25MPa左右),溫度為50~400℃左右(理想為100~350℃左右),時間為10分鐘~10小時左右(理想為20分鐘~7小時左右)。又,前述氫化條件並不排除數值範圍外之條件,例如,若雖然壓力小於1MPa但是使用可引起反應之觸媒而能夠進行氫化,則亦可以在該條件下進行。
用於氫化反應之觸媒,可列舉:鎳、鈀、鉑、鈷、銠、釕、錸等金屬或者此等之氧化物、硫化物等金屬化合物等。此外,前述觸媒亦可以負載於多孔且表面積大的氧化鋁、二氧化矽、二氧化矽氧化鋁(矽藻土)、碳、二氧化鈦等載體並使用。
觸媒之使用量,相對於前述聚合物,通常為0.01~10重量%左右。
前述氫化反應在將前述聚合物熔融、或溶解於有機溶劑之狀態下進行。有機溶劑,只要是氫化反應時呈惰性且能夠溶解原料之前述聚合物及反應物之(a1)成分的物質,則沒有特別地限定,可列舉例如:四氫呋喃、二噁烷等環內具有氧原子的化合物;正己烷、正庚烷、正辛烷、2-乙基己烷等脂肪族烴;環己烷、十氫萘等脂環族烴;異丙醇、正丁醇、2-甲基-2-丙醇、環己醇、正己醇、2-乙基己醇等醇等。此等可以為單獨,亦可以組合2種以上。有機溶劑之使用量,沒有特別地限定,但以反應濃度計,理想進行調整以使其通常為95重量%以下、理想為30~90重量%。
所得之(a1)成分之物性,例如,羥值通常為80~250mgKOH/g,理想為100~240mgKOH/g。藉由設為該範圍,從而具有色調良好且容易與(a2)成分或(a3)成分反應之傾向。又,羥值係依照JIS K-0070之測定值。
此外,(a1)成分之軟化點通常為90~120℃,理想為95~115℃。又,軟化點係依照JIS K-5902之測定值。
(a2)成分係具有1個異氰酸酯基之(甲基)丙烯酸酯,並且係有助於硬化物之硬度及低透濕性之成分。(a2)成分,可列舉例如:(甲基)丙烯酸2-異氰酸基乙酯、(甲基)丙烯酸3-異氰酸基丙酯、(甲基)丙烯酸4-丁基異氰酸基丁酯等(甲基)丙烯酸異氰酸基烷酯;2-(2-甲基丙烯醯氧基乙基氧基)乙基異氰酸酯、1,1-(雙丙烯醯氧基甲基)乙基異氰酸酯等。此外,作為市售品,可以使用昭和電工(股)製之「Karenz AOI」、「Karenz MOI」、「Karenz MOI-EG」、「Karenz BEI」等。此等可為單獨,亦可組合2種以上。其中,從與(a1)成分之反應性及硬化物之低透濕性之觀點而言,理想係(甲基)丙烯酸異氰酸基烷酯。
(a2)成分之使用量,沒有特別地限定,以(a2)成分中之異氰酸酯基數(NCO
( a2 ))與(a1)成分中之羥基數(OH
( a1 ))之比率計,理想為[(NCO
( a2 ))/(OH
( a1 ))]= 0.90~1.05,更理想為0.95~1.00。
(A1)成分可藉由使(a1)成分及(a2)成分反應而得到。其條件,沒有特別地限定,例如,通常,溫度為50~100℃左右(理想為60~80℃左右),時間為0.1~6小時左右(理想為0.5~2小時左右)。
又,(A1)成分之製造可以在前述有機溶劑中、或無溶劑下之任一條件下進行。
由此而得之(A1)成分之物性,沒有特別地限定,例如,重量平均分子量理想為300~10000左右,更理想為500~7000左右。又,在此之重量平均分子量係藉由GPC法(採用凝膠滲透層析法之聚苯乙烯換算值)而測定之值。(以下相同)
接著,對本發明之胺基甲酸酯(甲基)丙烯酸酯(A2)(以下亦稱為(A2)成分。)進行說明。
關於(a1)成分,如前述段落所記載。
(a3)成分,沒有特別地限定,可列舉例如:六亞甲基二異氰酸酯、三甲基六亞甲基二異氰酸酯、離胺酸二異氰酸酯等脂肪族多異氰酸酯;二環己基甲烷-4,4’-二異氰酸酯、異佛爾酮二異氰酸酯、1,4-環己烷二異氰酸酯、降莰烯甲烷二異氰酸酯(norbornene methane diisocyanate)、環己-1,4-二基雙(亞甲基)二異氰酸酯、氫化苯二甲基二異氰酸酯、氫化甲苯二異氰酸酯、氫化四甲基苯二甲基二異氰酸酯、氫化二苯基甲烷二異氰酸酯、氫化二甲基二苯基甲烷二異氰酸酯、氫化萘二異氰酸酯等脂環族多異氰酸酯;苯二甲基二異氰酸酯、甲苯二異氰酸酯、四甲基苯二甲基二異氰酸酯、二苯基甲烷二異氰酸酯、二甲基二苯基甲烷二異氰酸酯、萘二異氰酸酯等芳香族多異氰酸酯等。又,此等可為單獨,亦可組合2種以上。此外,(a3)成分,亦可以使用具有異氰脲酸酯體、加成物、縮二脲體中之任一種結構之物質。其中,從硬化物之低透濕性之觀點而言,理想為脂環族多異氰酸酯,更理想為異佛爾酮二異氰酸酯、降莰烯甲烷二異氰酸酯、氫化苯二甲基二異氰酸酯。
(a3)成分之使用量,沒有特別地限定,但以(a3)成分中之異氰酸酯基數(NCO
( a3 ))與(a1)成分中之羥基數(OH
( a1 ))之比率計,理想為[(NCO
( a3 ))/(OH
( a1 ))]= 0.90~1.05,更理想為0.95~1.00。
(a4)成分,可列舉例如:(甲基)丙烯酸2-羥乙酯、(甲基)丙烯酸2-羥丙酯、丙烯酸3-羥丙酯、(甲基)丙烯酸2-羥丁酯、(甲基)丙烯酸3-羥丁酯、(甲基)丙烯酸4-羥丁酯、(甲基)丙烯酸6-羥己酯等具有羥基之脂肪族單(甲基)丙烯酸酯;(甲基)丙烯酸4-羥基環己酯、(甲基)丙烯酸5-羥基環辛酯等具有羥基之脂環族單(甲基)丙烯酸酯;(甲基)丙烯酸2-羥基-3-苯氧基丙酯、聚乙二醇單(甲基)丙烯酸酯、聚丙二醇單(甲基)丙烯酸酯等具有羥基及醚鏈之單(甲基)丙烯酸酯;赤藻糖醇二(甲基)丙烯酸酯、赤藻糖醇三(甲基)丙烯酸酯等赤藻糖醇(甲基)丙烯酸酯類;新戊四醇單(甲基)丙烯酸酯、新戊四醇二(甲基)丙烯酸酯、新戊四醇三(甲基)丙烯酸酯等新戊四醇(甲基)丙烯酸酯類;二新戊四醇單(甲基)丙烯酸酯、二新戊四醇二(甲基)丙烯酸酯、二新戊四醇三(甲基)丙烯酸酯、二新戊四醇四(甲基)丙烯酸酯、二新戊四醇五(甲基)丙烯酸酯等二新戊四醇(甲基)丙烯酸酯類;三新戊四醇四(甲基)丙烯酸酯、三新戊四醇五(甲基)丙烯酸酯、三新戊四醇六(甲基)丙烯酸酯、三新戊四醇七(甲基)丙烯酸酯等三新戊四醇(甲基)丙烯酸酯類等。此等可為單獨,亦可組合2種以上。其中,從與異氰酸酯基之反應性及硬化物之低透濕性之觀點而言,理想為(甲基)丙烯酸2-羥乙酯、(甲基)丙烯酸2-羥丙酯、(甲基)丙烯酸4-羥丁酯、新戊四醇(甲基)丙烯酸酯類,更理想為丙烯酸2-羥乙酯。
又,前述(a4)成分,亦可以使用含有不含羥基之聚(甲基)丙烯酸酯之混合物。不含羥基之聚(甲基)丙烯酸酯,沒有特別地限定,可列舉例如:赤藻糖醇四(甲基)丙烯酸酯、新戊四醇四(甲基)丙烯酸酯、二新戊四醇六(甲基)丙烯酸酯、三新戊四醇八(甲基)丙烯酸酯等。不含羥基之聚(甲基)丙烯酸酯之含量,相對於(a4)成分100重量%,為60重量%以下。
作為(a4)成分之市售品,可列舉例如:「ARONIX M305」、「ARONIX M306」、「ARONIX M400」、「ARONIX M402」、「ARONIX M403」、「ARONIX M404」、「ARONIX M405」、「ARONIX M406」、「ARONIX M933」(東亞合成(股)製);「KAYARAD DPHA」(日本化藥(股)製);「A-9550」、「A-DPH」(新中村化學工業(股)製);「Viscoat#300」、「Viscoat#802」(大阪有機化學工業(股)製);「Miramer M500」(MIWON Specialty Chemical Co, Ltd.製)等。
(a4)成分之使用量,沒有特別地限定,但從硬化物之低透濕性之觀點而言,以作為(a1)成分及(a3)之反應物之預聚物(以下亦稱為(a’)成分。)中之異氰酸酯基數(NCO
( a’))與(a4)成分中之羥基數(OH
( a4 ))之比率計,理想為[(NCO
( a’))/(OH
( a4 ))]= 0.90~1.05,更理想為0.95~1.00。
(A2)成分可以藉由各種習知的方法來製造,例如,可以藉由使(a1)成分與(a3)成分發生反應而生成預聚物(a’),接著使(a’)成分與(a4)成分發生反應而得到。反應條件,沒有特別地限定,例如,通常溫度為50~100℃左右(理想為60~80℃左右),時間為0.1~6小時左右(理想為0.5~2小時左右)。
又,(A2)成分之製造可以在前述有機溶劑中、或無溶劑下之任一條件下進行。
由此而得之(A2)成分之物性,沒有特別地限定,例如,重量平均分子量理想為500~20000左右,更理想為1000~12000左右。
本發明之活性能量射線硬化型樹脂組成物含有前述胺基甲酸酯(甲基)丙烯酸酯((A1)成分及/或(A2)成分)。
本發明之活性能量射線硬化型樹脂組成物亦可以進一步含有活性能量射線硬化型單體(B)(以下稱為(B)成分。)及/或金屬氧化物(C)。
(B)成分只要係前述胺基甲酸酯(甲基)丙烯酸酯以外之硬化型單體,則沒有特別地限定,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)丙烯酸正丁酯、(甲基)丙烯酸三級丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸正戊酯、(甲基)丙烯酸正己酯、(甲基)丙烯酸正庚酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸正壬酯、(甲基)丙烯酸正癸酯、(甲基)丙烯酸異癸酯、(甲基)丙烯酸三正癸酯、(甲基)丙烯酸正月桂酯、(甲基)丙烯酸正肉豆蔻酯、(甲基)丙烯酸正棕櫚酯、(甲基)丙烯酸正硬脂酯、(甲基)丙烯酸異硬脂酯等脂肪族(甲基)丙烯酸酯;
(甲基)丙烯酸環己酯、(甲基)丙烯酸降莰酯(norbornyl (meth)acrylate)、(甲基)丙烯酸異莰酯、(甲基)丙烯酸降莰烷酯(norbornanyl (meth)acrylate)、(甲基)丙烯酸二環戊烯酯(dicyclopentenyl (meth)acrylate)、(甲基)丙烯酸二環戊烯基氧基乙酯、(甲基)丙烯酸二環戊酯(dicyclopentanyl (meth)acrylate)、(甲基)丙烯酸二環戊基氧基乙酯、三環癸二甲醇二(甲基)丙烯酸酯(tricyclodecanedimethylol di(meth)acrylate)等脂環族(甲基)丙烯酸酯;
(甲基)丙烯酸苯酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸2-苯基乙酯、壬基苯氧基聚乙二醇(甲基)丙烯酸酯等芳香族(甲基)丙烯酸酯;
(甲基)丙烯酸甲氧基乙酯、(甲基)丙烯酸乙氧基乙酯、(甲基)丙烯酸丁氧基乙酯、(甲基)丙烯酸2-甲氧基乙氧基乙酯、(甲基)丙烯酸2-乙氧基乙氧基乙酯等具有烷氧基烷基之(甲基)丙烯酸酯;
乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯等單烷二醇(甲基)丙烯酸酯;
二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、三丙二醇二(甲基)丙烯酸酯等聚烷二醇(甲基)丙烯酸酯;
甲氧基二乙二醇(甲基)丙烯酸酯、乙氧基二乙二醇(甲基)丙烯酸酯、甲氧基二丙二醇(甲基)丙烯酸酯等烷氧基聚烷二醇(甲基)丙烯酸酯;
(甲基)丙烯醯胺、二甲基(甲基)丙烯醯胺、二乙基(甲基)丙烯醯胺、(甲基)丙烯醯基嗎啉等(甲基)丙烯醯胺類;
(甲基)丙烯酸縮水甘油酯等具有環氧基之(甲基)丙烯酸酯;
(甲基)丙烯酸N,N-二甲基胺基乙酯、(甲基)丙烯酸N,N-二乙基胺基乙酯等(甲基)丙烯酸二烷基胺基烷酯;
新戊四醇單(甲基)丙烯酸酯、新戊四醇二(甲基)丙烯酸酯、新戊四醇三(甲基)丙烯酸酯、新戊四醇四(甲基)丙烯酸酯或其等之混合物之新戊四醇(甲基)丙烯酸酯類;
二新戊四醇單(甲基)丙烯酸酯、二新戊四醇二(甲基)丙烯酸酯、二新戊四醇三(甲基)丙烯酸酯、二新戊四醇四(甲基)丙烯酸酯、二新戊四醇五(甲基)丙烯酸酯、二新戊四醇六(甲基)丙烯酸酯或其等之混合物之二新戊四醇(甲基)丙烯酸酯類;
三新戊四醇四(甲基)丙烯酸酯、三新戊四醇五(甲基)丙烯酸酯、三新戊四醇六(甲基)丙烯酸酯、三新戊四醇七(甲基)丙烯酸酯、三新戊四醇八(甲基)丙烯酸酯或其等之混合物之三新戊四醇(甲基)丙烯酸酯類;
三羥甲基丙烷三(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯等。
此等(B)成分可為單獨,亦可組合2種以上。其中,從硬化物之硬度之觀點而言,理想為新戊四醇(甲基)丙烯酸酯類、二新戊四醇(甲基)丙烯酸酯類、三新戊四醇(甲基)丙烯酸酯類,更理想為二新戊四醇(甲基)丙烯酸酯類。
在使用(B)成分作為活性能量射線硬化型樹脂組成物之成分之情況下,其含量,從硬化物之低透濕性之觀點而言,以固體成分重量比率計而在(A1)成分、(A2)成分及(B)成分之合計100重量%中,通常為1~80重量%,理想為1~50重量%。
(C)成分,沒有特別地限定,可列舉例如:二氧化矽、氧化鋁、氧化鋯、氧化鈦、氧化銻、氧化錫、氧化銦、氧化鋅等。又,(C)成分,亦可以使用以鋁、磷、氟等摻雜後之物質。此等可為單獨,亦可組合2種以上。
此外,作為市售品,可列舉:「TOL-ST」、「MEK-ST-40」、「MEK-ST-L」、「MEK-ST-ZL」、「MEK-ST-UP」、「MIBK-ST」、「CHO-ST-M」、「EAC-ST」、「PMA-ST」(以上,日產化學(股)製)等。
此外,(C)成分,亦可以使用在表面具有有機官能基之金屬氧化物。「有機官能基」,係指至少具有碳原子之基團,可列舉例如:甲基丙烯醯基、丙烯醯基、乙烯基、環氧基、異氰酸酯基、胺基甲酸酯基、有機矽氧烷基等。
在表面具有有機官能基之金屬氧化物之市售品,可列舉例如:「MEK-EC-2130Y」、「MEK-AC2140Z」、「MEK-AC-4130Y」、「PGM-AC2140Y」、「PGM-AC3140Y」、「PGM-AC4130Y」、「MIBK-SD」、「MIBK-SD-L」(日產化學(股)製);「NANOBYK-3603」、「NANOBYK-3610」、「NANOBYK-3650」、「NANOBYK-3652」(日本畢克化學(BYK Chemie·Japan)(股)製);「ALMIBK30WT%-H06」、「SIRMIBK15ET%-H24」、「SIRMIBK15ET%-H83」(CIK NanoTek(股)製);「ELECOM-V#8802」、「ELECOM-V#8803」、「ELECOM-V#8804」(日揮觸媒化成(股)製)等。
(C)成分之平均一次粒徑,沒有特別地限定,但從硬化物之透明性之觀點而言,理想為4~200nm左右,更理想為7~50nm左右。又,平均一次粒徑之測定方法,沒有特別地限定,可列舉例如光散射法等。
在使用(C)成分作為活性能量射線硬化型樹脂組成物之成分之情況下,其含量,從硬化物之柔軟性之觀點而言,以固體成分重量比率計,本發明之胺基甲酸酯(甲基)丙烯酸酯及(C)成分之合計100重量%中,通常為1~70重量%,理想為1~50重量%。
本發明之活性能量射線硬化型樹脂組成物,亦可以進一步含有有機溶劑。
有機溶劑,沒有特別地限定,可列舉例如:苯、甲苯、乙苯、正丙苯、三級丁苯、鄰二甲苯、間二甲苯、對二甲苯、四氫萘、十氫萘、芳香族石腦油等芳香族烴;正己烷、正庚烷、正辛烷、異辛烷、正癸烷等脂肪族烴;環己烷等脂環族烴;乙酸乙酯、乙酸丙酯、乙酸正丁酯、乙酸二級丁酯、乙酸三級丁酯、乙酸正戊酯、乙酸2-羥基乙酯、乙酸2-甲氧基乙酯、乙酸2-丁氧基乙酯、乙酸3-甲氧基丁酯、乙酸1-甲氧基丙酯、苯甲酸甲酯等酯;丙酮、甲乙酮、甲基異丁基酮、異佛爾酮、環己酮、甲基環己酮等酮;碳酸二甲酯、碳酸二乙酯、碳酸伸乙酯等碳酸酯;二異丙醚、乙二醇二甲醚、乙二醇二***、二乙二醇二甲醚等非環狀醚;四氫呋喃、1,3-二氧雜環戊烷、1,4-二噁烷等環狀醚;乙二醇單甲醚、乙二醇單***、乙二醇單丁醚、二乙二醇單甲醚、二乙二醇單***、二乙二醇單丁醚等單羥基醚;甲醇、乙醇、正丙醇、2-丙醇、正丁醇、異丁醇、二級丁醇、三級丁醇等醇等。此外,在使用有機溶劑作為活性能量射線硬化型樹脂組成物之成分之情況下,其含量,理想為0.5~80重量%。
本發明之活性能量射線硬化型樹脂組成物進一步含有光聚合引發劑。又,光聚合引發劑,可以在製備活性能量射線硬化型樹脂組成物時進行配合,亦可以在即將塗布於基材薄膜之前進行配合。
光聚合引發劑,沒有特別地限定,可列舉例如:苯偶姻化合物、苯乙酮化合物、醯基氧化膦化合物、二茂鈦化合物、噻噸酮化合物、肟酯化合物等光聚合引發劑,胺、醌等光敏劑;更具體而言,可列舉:2,2-二甲氧基-1,2-二苯基乙-1-酮、1-羥基環己基苯基酮、2-羥基-2-甲基-1-苯基丙-1-酮、1-[4-(2-羥基乙氧基)苯基]-2-羥基-2-甲基-1-丙-1-酮、2-羥基-1-[4-[4-(2-羥基-2-甲基丙醯基)苄基]苯基]-2-甲基丙-1-酮、2-甲基-1-(4-甲硫基苯基)-2-(N-嗎啉基)丙-1-酮、2-(二甲基胺基)-2-[(4-甲基苯基)甲基]-1-[4-(4-嗎啉基)苯基]-1-丁酮、2,4,6-三甲基苯甲醯基二苯基氧化膦、雙(2,4,6-三甲基苯甲醯基)-苯基氧化膦、雙(η
5-2,4-環戊二烯-1-基)-雙(2,6-二氟-3-(1H-吡咯-1-基)苯基)鈦、1,2-辛二酮1-[4-(苯硫基)-2-(O-苯甲醯基肟)](1,2-octanedione 1-[4-(phenylthio)-2-(o-benzoyloxime)])、乙酮1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]-1-(O-乙醯基肟)(ethanone 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-1-(o-acetyloxime))等。此等可為單獨,亦可組合2種以上。此外,光聚合引發劑之含量,相對於本發明之胺基甲酸酯(甲基)丙烯酸酯、(B)成分及(C)成分之合計100重量份,理想為0.5~20重量份,更理想為2~10重量份。
本發明之活性能量射線硬化型樹脂組成物亦可以進一步含有表面調整劑、界面活性劑、紫外線吸收劑、抗氧化劑、光穩定劑、矽烷偶聯劑、膠體二氧化矽、消泡劑、潤濕劑、防銹劑、調平劑等添加劑。
本發明之活性能量射線硬化型樹脂組成物,可以藉由混合前述胺基甲酸酯(甲基)丙烯酸酯、(B)成分及(C)成分、光聚合引發劑、根據需要之有機溶劑、以及前述添加劑而得到。混合手段及混合順序沒有特別地限定。
本發明之硬化物係使前述活性能量射線硬化型樹脂組成物硬化而成。
本發明之硬化物沒有特別地限定,例如,可以藉由將前述活性能量射線硬化型樹脂組成物塗布於基材薄膜,並照射活性能量射線而得到。
基材薄膜,為了使所得之積層體顯示低透濕性,理想係使用透濕度為200g/m
2・24h以上之基材薄膜。又,透濕度係依照JIS Z 0208,並在溫度40℃及濕度90%之相對濕度之環境下藉由杯法測定而得之值。(以下相同)
前述基材薄膜,可列舉例如:二乙酸纖維素薄膜、三乙酸纖維素薄膜、乙酸丙酸纖維素薄膜、乙酸丁酸纖維素薄膜等纖維素酯系薄膜;聚乙烯醇薄膜、乙烯乙烯醇薄膜等聚乙烯醇系薄膜;玻璃紙、聚醯胺薄膜、聚乳酸薄膜等。又,基材薄膜,可以使用輕剝離之基材薄膜、或重剝離之基材薄膜,此外可以使用未處理之基材薄膜、經電漿處理後之基材薄膜。
此外,為了使其容易與硬化物之層剝離,可以對前述基材薄膜進行剝離處理。剝離處理,在容易剝離之情況下並非特別必要,但為了使其更加容易剝離,可以積層三聚氰胺樹脂、矽樹脂、氟樹脂、纖維素衍生物、脲樹脂、聚烯烴樹脂、石蠟樹脂作為離型層。此等基材薄膜可為單獨,亦可組合2種以上。
前述基材薄膜之厚度,沒有特別地限定,通常為12~500μm左右,理想為25~200μm。
塗布方法,沒有特別地限定,可列舉例如:敷貼器(applicator)、刮棒塗布機、輥塗布機、刮刀塗布機、凹版塗布機、噴塗布機、逗號塗布機(comma coater)、唇塗布機(lip coater)、凹版印刷、網版印刷等。活性能量射線硬化型塗覆劑組成物之塗布量亦沒有特別地限定,通常,以照射後之硬化物之膜厚成為1~50μm左右之方式進行塗布。
塗布後,可以照射活性能量射線,亦可以將塗布被膜加熱乾燥以使其部分地硬化。又,在加熱乾燥之情況下,理想為在溫度40~100℃左右乾燥20秒~10分鐘。
活性能量射線,沒有特別地限定,可列舉例如:紫外線、紅外線、可見光等光線;電子束、X射線、α射線、β射線、γ射線、中子射線等。在本發明中,理想為光線,更理想為紫外線。
紫外線之光源,沒有特別地限定,可列舉例如:氙氣燈、高壓汞燈、超高壓汞燈、碳弧燈、金屬鹵化物燈、化學燈、無電極燈、LED燈等。此外,紫外線之累積照射量及輸送速度亦沒有特別地限定,累積照射量通常為100~3000mJ/cm
2,輸送速度通常為5~50m/min左右。此外,照射紫外線後,基於完全硬化之目的,亦可以根據需要進行加熱。
本發明之積層體係具有前述硬化物之層。所使用之基材薄膜及硬化方法等與前述相同。
所得之積層體之物性,透濕度為100g/m
2・24h以下,理想為80g/m
2・24h以下,更理想為70g/m
2・24h以下。
[實施例]
以下,列舉實施例,進一步具體地說明本發明,但並不限定本發明。此外,只要沒有特別的說明,則「份」、「%」均是重量基準。
<環戊二烯/烯丙醇聚合物之製造>
以表1所示之比例向1升容積高壓釜中裝入雙環戊二烯280份、烯丙醇120份及作為溶劑之甲苯150份,實施氮取代後,在250℃保溫,進行6小時反應。接著,取出所得之醇改性雙環戊二烯系聚合物溶液,在240℃、1.0kPa之條件下以30分鐘減壓蒸餾去除甲苯、未反應物及低沸點成分,而得到軟化點100℃、色調12G、羥值240mg/KOH之雙環戊二烯/烯丙醇聚合物(以下稱為DCPDA樹脂。)。
製造例a
向高壓釜中裝入DCPDA樹脂500份、鎳/矽藻土觸媒(鎳負載量50重量%)7份,在280℃保溫,在氫壓力20MPa下進行氫化5小時。接著,取出反應溶液,溶解於甲苯500份,藉由過濾除去觸媒後,在200℃、2.7kPa之條件下,以30分鐘在減壓下蒸餾去除甲苯,得到軟化點105℃、色調150哈森(Hazen)、羥值100mg/KOH之DCPDA樹脂之氫化物450份。
製造例b
向高壓釜中裝入DCPDA樹脂500份、鎳/矽藻土觸媒(鎳負載量50重量%)7份,在250℃保溫,在氫壓力20MPa下進行氫化5小時。接著,取出反應溶液,溶解於甲苯500份,藉由過濾除去觸媒後,在200℃、2.7kPa之條件下,以30分鐘在減壓下蒸餾去除甲苯,得到軟化點105℃、色調200哈森、羥值200mg/KOH之DCPDA樹脂之氫化物450份。
製造例c
向高壓釜中裝入苯乙烯/烯丙醇聚合物(Sigma-Aldrich製,軟化點102.5℃、數量平均分子量950)(以下稱為STA樹脂。)500份、鎳/矽藻土觸媒(鎳負載量50重量%)7份,在250℃保溫,在氫壓力20MPa下進行氫化5小時。接著,取出反應溶液,溶解於甲苯500份,藉由過濾除去觸媒後,在200℃、2.7kPa之條件下,以30分鐘在減壓下蒸餾去除甲苯,得到軟化點100℃、色調120哈森、羥值100mg/KOH之STA樹脂之氫化物450份。
製造例1
向安裝有攪拌機、溫度計、回流冷凝管之三口燒瓶中,加入製造例a中所得之DCPDA樹脂之氫化物40份及甲苯40份、丙烯酸2-異氰酸基乙酯8.1份、辛酸錫0.02份、氫醌單甲醚0.05份,在80℃下進行反應至殘存異氰酸酯基為0.1%以下為止,得到固體成分濃度55%之胺基甲酸酯(甲基)丙烯酸酯(A-1)的溶液。
製造例2
在製造例1中,將丙烯酸2-異氰酸基乙酯變更為4.2份,並進行相同的操作,得到固體成分濃度52%之胺基甲酸酯(甲基)丙烯酸酯(A-2)的溶液。
製造例3
向與製造例1相同之三口燒瓶中,加入在製造例b中所得之DCPDA樹脂之氫化物40份及甲苯40份、丙烯酸2-異氰酸基乙酯16.1份、辛酸錫0.02份、氫醌單甲醚0.05份,在80℃下進行反應至殘存異氰酸酯基為0.1%以下為止,得到固體成分濃度58%之胺基甲酸酯(甲基)丙烯酸酯(A-3)的溶液。
製造例4
向與製造例1相同之三口燒瓶中,加入在製造例a中所得之DCPDA樹脂之氫化物40份及甲苯41份、氫化苯二甲基二異氰酸酯13.8份、辛酸錫0.02份,在80℃下反應2小時。其後加入丙烯酸2-羥乙酯(HEA)8.5份、辛酸錫0.01份、氫醌單甲醚0.07份,進行反應至殘存異氰酸酯基為0.1%以下為止,得到固體成分濃度60%之胺基甲酸酯(甲基)丙烯酸酯(A-4)的溶液。
製造例5
向與製造例1相同之三口燒瓶中,加入在製造例a中所得之DCPDA樹脂之氫化物40份及甲苯43份、異佛爾酮二異氰酸酯15.8份、辛酸錫0.02份,在80℃下反應2小時。其後加入丙烯酸2-羥乙酯(HEA)8.5份、辛酸錫0.01份、氫醌單甲醚0.07份,進行反應至殘存異氰酸酯基為0.1%以下為止,得到固體成分濃度60%之胺基甲酸酯(甲基)丙烯酸酯(A-5)的溶液。
製造例6
向與製造例1相同之三口燒瓶中,加入在製造例a中所得之DCPDA樹脂之氫化物40份及甲苯57.1份、氫化苯二甲基二異氰酸酯13.8份、辛酸錫0.01份,在80℃下反應2小時。其後,加入新戊四醇三丙烯酸酯及新戊四醇四丙烯酸酯之混合物(商品名:「ARONIX M-305」,東亞合成(股)製)(PETA)33.2份、辛酸錫0.03份、氫醌單甲醚0.07份,進行反應至殘存異氰酸酯基為0.1%以下為止,得到固體成分濃度60%之胺基甲酸酯(甲基)丙烯酸酯(A-6)的溶液。
製造例7
在製造例1中,從製造例a之DCPDA樹脂之氫化物變更為製造例c中所得之STA樹脂之氫化物,並進行相同的操作,得到固體成分濃度55%之胺基甲酸酯(甲基)丙烯酸酯(A-7)的溶液。
比較製造例1
在製造例1中,變更為DCPDA樹脂(未氫化之聚合物),並進行相同的操作,得到固體成分濃度55%之胺基甲酸酯(甲基)丙烯酸酯(A-8)的溶液。
實施例1
將製造例1中所得之(A-1)的溶液100份(固體成分重量:55份)、1-羥基環己基苯基酮(光聚合引發劑,商品名:「Omnirad184」,IGM Resins B.V.公司製)1.5份、矽酮系表面調整劑(添加劑,商品名:「BYK-UV3570」,BYK公司製)0.2份、及甲乙酮13.5份進行配合,並進行攪拌至溶解為止,而製備活性能量射線硬化型樹脂組成物。
實施例2~6、比較例1~2
將表1所示之(A)成分之溶液配合100份,分別製備活性能量射線硬化型樹脂組成物。又,在比較例2中,使用60份在製造例a中所得之DCPDA樹脂之氫化物。
(積層體)
在三乙酸纖維素薄膜(商品名:「FT TD60ULP」,富士軟片(股)製,透濕度:500g/m
2・24h、厚度:60μm)上,以硬化後之膜厚為6μm之方式藉由#16刮棒塗布機塗布各活性能量射線硬化型樹脂組成物,並在80℃下乾燥1分鐘。接著,使用高壓汞燈(產品名:「UBT-080-7A/BM」,(股)Multiply製),照射累積照射量600mJ/cm
2,而得到積層體。
(透濕度)
使用各積層體,依照JIS Z 0208之透濕度試驗法(杯法)進行測定。在溫度40℃及濕度90%之環境中,測定積層體之每1m
2面積24小時所通過之水蒸氣之克數。克數越小,則表示越良好。
(鉛筆硬度)
依照JIS K 5600-5-4,藉由荷重500g之鉛筆劃痕試驗,測定各積層體之硬化物之硬度。將6B以上設為良好。
(耐光性)
藉由紫外線自動褪色計(商品名:「紫外線自動褪色計U48AU」,須賀試驗機(股)製),在碳弧燈下將各積層體曝光50小時。藉由色差計(商品名:ZE 6000,日本電色工業(股)製)之透射法,測定曝光後之積層體之黃色指數值。若測定值小於3則設為「○」,若為3以上則設為「×」。
同樣地,亦對向(A-1)成分配合活性能量射線硬化型單體及/或金屬氧化物而得之活性能量射線硬化型樹脂組成物進行評價。以下,詳細地進行記載。
實施例7
將製造例1中所得之(A-1)的溶液50份(固體成分重量:27.5份)、二新戊四醇五丙烯酸酯及二新戊四醇六丙烯酸酯之混合物(商品名:「ARONIX M402」,東亞合成(股)製)27.5份、1-羥基環己基苯基酮(光聚合引發劑,商品名:「Omnirad184」,IGM Resins B.V.公司製)1.5份、矽酮系表面調整劑(添加劑,商品名:「BYK-UV3570」,BYK公司製)0.2份、及甲乙酮13.5份進行配合,並進行攪拌至溶解為止,而製備活性能量射線硬化型樹脂組成物。
實施例8
將製造例1中所得之(A-1)的溶液50份(固體成分重量:27.5份)、二氧化矽(商品名:「MIBK-SD」,固體成分濃度:30%、粒徑:10~15nm,日產化學(股)製)91.6份(固體成分重量:27.5份)、1-羥基環己基苯基酮(光聚合引發劑,商品名:「Omnirad184」,IGM Resins B.V.公司製)1.5份、矽酮系表面調整劑(添加劑,商品名:「Tegorad2011」,Evonik INTERNATIONAL B.V.公司製)0.2份、及甲乙酮13.5份進行配合,並進行攪拌至溶解為止,而製備活性能量射線硬化型樹脂組成物。
比較例3
在實施例7中,將製造例a中所得之DCPDA樹脂之氫化物變更為27.5份而進行,製備活性能量射線硬化型樹脂組成物。
藉由與上述相同之方法,測定實施例7、8及比較例3之活性能量射線硬化型樹脂組成物之透濕度、鉛筆硬度及耐光性。結果示於表2中。
表2中之簡稱表示以下化合物。
・DPHA:二新戊四醇五丙烯酸酯及二新戊四醇六丙烯酸酯之混合物(商品名:「ARONIX M402」,東亞合成(股)製)
・Si:二氧化矽(商品名:「MIBK-SD」,固體成分濃度:30%、粒徑:10~15nm,日產化學(股)製)。
Claims (10)
- 一種胺基甲酸酯(甲基)丙烯酸酯,其特徵係其為下述聚合物之氫化物(a1)、與下述(I)及/或(II)之反應物; 該聚合物係具有烯烴性雙鍵及環狀結構之烴(a1-1)與具有活性氫之化合物(a1-2)之聚合物; (I)具有1個異氰酸酯基之(甲基)丙烯酸酯(a2); (II)多異氰酸酯(a3)及具有羥基之(甲基)丙烯酸酯(a4)。
- 如請求項1所述之胺基甲酸酯(甲基)丙烯酸酯,其中,(a1-1)成分含有雙環戊二烯類及/或苯乙烯類。
- 如請求項1或2所述之胺基甲酸酯(甲基)丙烯酸酯,其中,(a1-2)成分含有不飽和脂肪族醇。
- 如請求項1~3中任一項所述之胺基甲酸酯(甲基)丙烯酸酯,其中,(a2)成分為(甲基)丙烯酸異氰酸基烷酯。
- 如請求項1~4中任一項所述之胺基甲酸酯(甲基)丙烯酸酯,其中,(a3)成分為脂環族多異氰酸酯。
- 一種活性能量射線硬化型樹脂組成物,其特徵係含有如請求項1~5中任一項所述之胺基甲酸酯(甲基)丙烯酸酯。
- 如請求項6所述之活性能量射線硬化型樹脂組成物,其中,其進一步含有活性能量射線硬化型單體(B)及/或金屬氧化物(C)。
- 一種硬化物,其特徵係其為如請求項6或7所述之活性能量射線硬化型樹脂組成物之硬化物。
- 一種積層體,其特徵係在透濕度為200g/m 2・24h以上之基材薄膜之至少單面具有如請求項8所述之硬化物。
- 如請求項9所述之積層體,其中,其透濕度為100g/m 2・24h以下。
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