TWI727026B - Hardenable composition, method of manufacturing hardened material and hardened material - Google Patents
Hardenable composition, method of manufacturing hardened material and hardened material Download PDFInfo
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- TWI727026B TWI727026B TW106110860A TW106110860A TWI727026B TW I727026 B TWI727026 B TW I727026B TW 106110860 A TW106110860 A TW 106110860A TW 106110860 A TW106110860 A TW 106110860A TW I727026 B TWI727026 B TW I727026B
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- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-O thiolan-1-ium Chemical compound C1CC[SH+]C1 RAOIDOHSFRTOEL-UHFFFAOYSA-O 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- GJOGTGLNIWPDPF-UHFFFAOYSA-N trifluoromethyl hydrogen sulfite Chemical compound OS(=O)OC(F)(F)F GJOGTGLNIWPDPF-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 229920006305 unsaturated polyester Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
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- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
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- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/18—Oxetanes
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- C08K5/00—Use of organic ingredients
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- C08K5/00—Use of organic ingredients
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- C08K5/10—Esters; Ether-esters
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Abstract
本發明係提供硬化物之玻璃轉移溫度高,密著性優異的硬化性組成物、硬化物之製造方法及其硬化物。 The present invention provides a curable composition with a high glass transition temperature and excellent adhesion of a cured product, a method for manufacturing a cured product, and a cured product.
本發明之硬化性組成物,其係含有:陽離子聚合性成分(A)、陽離子聚合起始劑(B)、自由基聚合性成分(C)、自由基聚合起始劑(D)及選自由下述式(I) The curable composition of the present invention contains: cationic polymerizable component (A), cationic polymerization initiator (B), radical polymerizable component (C), radical polymerization initiator (D) and selected from The following formula (I)
Description
本發明係有關硬化性組成物、硬化物之製造方法及其硬化物,詳細為有關硬化物之玻璃轉移溫度高,密著性優異的硬化性組成物、硬化物之製造方法及其硬化物。 The present invention relates to a curable composition, a method for manufacturing a cured product, and a cured product, and in detail, a curable composition with a high glass transition temperature and excellent adhesion, a method for manufacturing a cured product, and a cured product.
硬化性組成物係使用於油墨、塗料、各種塗覆劑、接著劑、光學構件等的領域。關於這種硬化性組成物之改良,有各種的報告。 The curable composition is used in fields such as inks, paints, various coating agents, adhesives, and optical components. There are various reports on the improvement of this kind of curable composition.
例如下述專利文獻1~4中提案含有陽離子聚合性成分及自由基聚合性成分之能量線硬化性組成物及其硬化物。具體而言,專利文獻1中,提案初期硬化性及接著性優異的偏光板用接著劑組成物。又,專利文獻2、3中,提案即使以透濕度低之樹脂薄膜作為保護膜時,光照射後,也能快速展現接著力,且經過一定時間後對於各種力,接著力為良好,耐久試驗後亦不發生問題,耐濕熱試驗結束後之接著力亦良好之低黏度的光硬化性接著劑。此外,專利文獻4中,提案含有不飽和脂環式環氧酯化合物可兼具高耐熱性或高折射率化與透明性的活性能量線聚合 性樹脂組成物。 For example, the following Patent Documents 1 to 4 propose energy ray curable compositions containing cationically polymerizable components and radically polymerizable components and their cured products. Specifically, Patent Document 1 proposes an adhesive composition for polarizing plates that is excellent in initial curability and adhesiveness. In addition, in Patent Documents 2 and 3, it is proposed that even when a resin film with low moisture permeability is used as a protective film, the adhesive force can be quickly exhibited after light irradiation, and after a certain period of time, the adhesive force is good for various forces. Endurance test There is no problem afterwards, and the adhesive force after the end of the damp heat resistance test is also a low-viscosity light-curing adhesive. In addition, Patent Document 4 proposes an active energy ray polymerization containing an unsaturated alicyclic epoxy ester compound that can have both high heat resistance or high refractive index and transparency. 性resin composition.
專利文獻1:日本特開2014-105218號公報 Patent Document 1: JP 2014-105218 A
專利文獻2:日本特開2015-040283號公報 Patent Document 2: Japanese Patent Application Publication No. 2015-040283
專利文獻3:日本特開2015-143352號公報 Patent Document 3: Japanese Patent Application Publication No. 2015-143352
專利文獻4:日本特開2015-168757號公報 Patent Document 4: Japanese Patent Application Publication No. 2015-168757
但是,即使為專利文獻1~4所提案之硬化性組成物,對於硬化性及密著性,亦有不一定能夠滿足的情況,現狀為期望能夠高度兼具硬化性及密著性之新穎的硬化性組成物。 However, even for the curable compositions proposed in Patent Documents 1 to 4, the curability and adhesiveness may not always be satisfied. The current situation is that it is desired to have a high degree of curability and adhesiveness. Hardening composition.
因此,本發明之目的為提供硬化物之玻璃轉移溫度高,密著性優異的硬化性組成物、硬化物之製造方法、及其硬化物。 Therefore, the object of the present invention is to provide a curable composition with a high glass transition temperature of the cured product and excellent adhesion, a method for manufacturing the cured product, and a cured product thereof.
本發明者等人為了解決上述課題而精心探討的結果,發現若為具有特定組成之硬化性組成物時,即可克服上述課題,而完成本發明。 The inventors of the present invention have intensively studied in order to solve the above-mentioned problems, and found that if it is a curable composition having a specific composition, the above-mentioned problems can be overcome and the present invention has been completed.
亦即,本發明之硬化性組成物,其係含有:
陽離子聚合性成分(A)、陽離子聚合起始劑(B)、自由基聚合性成分(C)、自由基聚合起始劑(D)及選自由下述式(I)
本發明之硬化性組成物中,前述陽離子聚合性成分(A)為進一步含有脂環式環氧化合物(A3)為佳。又,本發明之硬化性組成物中,前述分子量200以上之多元醇的環氧丙基化物、或多元醇環氧烷加成物之環氧丙基化物(A1)中之多元醇為具有縮合環的多元醇為佳。此外,本發明之硬化性組成物中,前述聚合物(E)為由前述式(I)表示之單體及前述式(II)表示之單體所得的聚合物,前述式(I)中之X為碳原子數6~12之芳基,前述式(II)中之X’為碳原子數1~7之烷基,前述烷基經環氧基取代為佳。又,前述陽離子聚合性成分(A)為30~70質量份,前述陽離子聚合起始劑(B)為0.001~10質量份,前述自由基聚合性成分(C)為30~60質量份,前述自由基聚合起始劑(D)為1~10質量份,前述聚合物(E) 為1~20質量份,且前述陽離子聚合性成分(A)與前述自由基聚合性成分(C)與前述聚合物(E)之合計為100質量份為佳。 In the curable composition of the present invention, the cationically polymerizable component (A) preferably further contains an alicyclic epoxy compound (A3). In addition, in the curable composition of the present invention, the glycidyl compound of the polyhydric alcohol with a molecular weight of 200 or more or the glycidyl compound (A1) of the polyhydric alcohol alkylene oxide adduct has a condensed Ring polyols are preferred. In addition, in the curable composition of the present invention, the aforementioned polymer (E) is a polymer obtained from the monomer represented by the aforementioned formula (I) and the aforementioned monomer represented by the aforementioned formula (II). X is an aryl group with 6 to 12 carbon atoms, X'in the aforementioned formula (II) is an alkyl group with 1 to 7 carbon atoms, and the aforementioned alkyl group is preferably substituted with an epoxy group. In addition, the cationic polymerizable component (A) is 30 to 70 parts by mass, the cationic polymerization initiator (B) is 0.001 to 10 parts by mass, and the radical polymerizable component (C) is 30 to 60 parts by mass. The radical polymerization initiator (D) is 1-10 parts by mass, the aforementioned polymer (E) It is 1 to 20 parts by mass, and the total of the above-mentioned cationically polymerizable component (A), the above-mentioned radically polymerizable component (C), and the above-mentioned polymer (E) is preferably 100 parts by mass.
本發明之硬化物之製造方法,其係將活性能量線照射或加熱本發明之硬化性組成物者。 The method for producing a hardened product of the present invention involves irradiating or heating the hardenable composition of the present invention with active energy rays.
本發明之硬化物係本發明之硬化性組成物的硬化物。 The cured product of the present invention is a cured product of the curable composition of the present invention.
依據本發明時,可提供硬化物之玻璃轉移溫度高,密著性優異的硬化性組成物、硬化物之製造方法及其硬化物。本發明之硬化性組成物,特別是可用於接著劑。 According to the present invention, it is possible to provide a curable composition with a high glass transition temperature of the cured product and excellent adhesion, a method for producing a cured product, and a cured product thereof. The curable composition of the present invention is particularly useful for adhesives.
以下詳細說明本發明之硬化性組成物。 The curable composition of the present invention will be described in detail below.
本發明之硬化性組成物,其係含有:陽離子聚合性成分(A)、陽離子聚合起始劑(B)、自由基聚合性成分(C)、自由基聚合起始劑(D)及選自由下述式(I)表示之單體所得之聚合物、由下述式(II)表示之單體所得之聚合物、選自下述式(I)表示之單體之二種以上之單體所得之聚合物、選自下述式(II)表示之單體之二種以上之單體所得之聚合物、及選自下述式(I)表示之單體及下述式(II)表示之單體所得之聚合物所成群組之重量 平均分子量1,000~30,000的聚合物(E)。本發明之硬化性組成物中,陽離子聚合性成分(A)係以分子量200以上之多元醇的環氧丙基化物、或多元醇環氧烷加成物之環氧丙基化物(A1)及氧雜環丁烷化合物(A2)作為必須成分,自由基聚合性成分(C)係以具有環氧基及乙烯性不飽和基之化合物(C1)、或碳原子數2~20之醇的丙烯酸酯或碳原子數2~20之醇的甲基丙烯酸酯(C2)作為必須成分。 The curable composition of the present invention contains: cationic polymerizable component (A), cationic polymerization initiator (B), radical polymerizable component (C), radical polymerization initiator (D) and selected from A polymer derived from a monomer represented by the following formula (I), a polymer derived from a monomer represented by the following formula (II), a monomer selected from two or more monomers represented by the following formula (I) The obtained polymer, the polymer obtained from two or more monomers selected from the monomer represented by the following formula (II), and the polymer selected from the monomer represented by the following formula (I) and the following formula (II) The weight of the group of the polymer obtained from the monomer Polymer (E) with an average molecular weight of 1,000 to 30,000. In the curable composition of the present invention, the cationically polymerizable component (A) is a glycidyl compound of a polyol having a molecular weight of 200 or more, or a glycidyl compound (A1) of a polyol alkylene oxide adduct, and The oxetane compound (A2) is an essential component, and the radically polymerizable component (C) is a compound (C1) having an epoxy group and an ethylenically unsaturated group, or acrylic acid of an alcohol with 2 to 20 carbon atoms Ester or methacrylate (C2) of alcohol with 2 to 20 carbon atoms is an essential component.
在此,式(I)中,X為碳原子數1~7之烷基、碳原子數1~7之烷氧基、碳原子數6~12之芳基、碳原子數6~12之芳氧基或碳原子數6~10之脂環式烴基,或此等之基中的氫原子為經選自由環氧基、氧雜環丁烷基、羥基及羧基所成群組之1種以上之基所取代者。 Here, in formula (I), X is an alkyl group with 1 to 7 carbon atoms, an alkoxy group with 1 to 7 carbon atoms, an aryl group with 6 to 12 carbon atoms, and an aromatic group with 6 to 12 carbon atoms. An oxy group or an alicyclic hydrocarbon group with 6 to 10 carbon atoms, or the hydrogen atom in these groups is one or more selected from the group consisting of epoxy group, oxetanyl group, hydroxyl group and carboxyl group Replaced by the base.
在此,式(II)中,R1表示氫原子、甲基或鹵素原子,X’為碳原子數1~7之烷基、碳原子數6~12之芳基或碳原子數6~10之脂環式烴基,或此等之基中的氫原子為經選 自由環氧基、氧雜環丁烷基、羥基及羧基所成群組之1種以上之基所取代者。 Here, in formula (II), R 1 represents a hydrogen atom, a methyl group or a halogen atom, and X'is an alkyl group with 1 to 7 carbon atoms, an aryl group with 6 to 12 carbon atoms, or 6 to 10 carbon atoms. The alicyclic hydrocarbon group or the hydrogen atom in these groups is substituted by one or more groups selected from the group consisting of epoxy group, oxetanyl group, hydroxyl group and carboxyl group.
本發明之硬化性組成物的陽離子聚合性成分(A)係藉由以能量線照射或加熱活性化的陽離子聚合起始劑,產生高分子化或交聯反應的化合物。可列舉環氧化合物、氧雜環丁烷化合物、乙烯醚化合物等。 The cationically polymerizable component (A) of the curable composition of the present invention is a compound that is polymerized or crosslinked by a cationic polymerization initiator activated by energy ray irradiation or heating. Examples include epoxy compounds, oxetane compounds, and vinyl ether compounds.
本發明之硬化性組成物的陽離子聚合性成分(A)係以分子量200以上之多元醇的環氧丙基化物或多元醇環氧烷加成物的環氧丙基化物(A1)及氧雜環丁烷化合物(A2)作為必須成分,但是也可使用其他的環氧化合物,例如脂環式環氧化合物(A3)及芳香族環氧化合物(A4)等。 The cationically polymerizable component (A) of the curable composition of the present invention is a glycidyl compound (A1) of a polyol having a molecular weight of 200 or more or a polyol alkylene oxide adduct (A1) and oxygen The cyclobutane compound (A2) is an essential component, but other epoxy compounds such as alicyclic epoxy compounds (A3) and aromatic epoxy compounds (A4) can also be used.
上述分子量200以上之多元醇之環氧丙基化物、或多元醇環氧烷加成物的環氧丙基化物(A1),可列舉將多元醇或多元醇環氧烷加成物進行環氧丙基化者,且環氧丙基化物的分子量為200以上。 The glycidyl compound of the polyol with a molecular weight of 200 or more or the glycidyl compound (A1) of the polyol alkylene oxide adduct can be exemplified by the epoxy resin of the polyol or polyol alkylene oxide adduct. It is propylated, and the molecular weight of the glycidate is 200 or more.
上述分子量200以上之多元醇的環氧丙基化物、或多元醇環氧烷加成物的環氧丙基化物(A1),可列舉1,4-丁二醇二環氧丙醚、1,6-己二醇二環氧丙醚、新戊二醇二環氧丙醚、丙三醇之三環氧丙醚、三羥甲基丙烷之三環氧丙醚、山梨醣醇之四環氧丙醚、二季戊四醇之六環氧丙醚、聚乙二醇之二環氧丙醚、聚丙二醇之二環氧丙醚、二環戊二烯二甲醇二環氧丙醚等之多元醇之環氧丙醚,及將1種或2種以上之環氧烷與丙二醇、三羥甲基丙 烷、丙三醇等之脂肪族多元醇進行加成所得之聚醚多元醇的聚環氧丙醚化物、脂肪族長鏈二元酸之二環氧丙酯。 The glycidyl product (A1) of the polyol having a molecular weight of 200 or more or the glycidyl product (A1) of the polyol alkylene oxide adduct includes 1,4-butanediol diglycidyl ether, 1, 6-Hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether, triglycidyl ether of glycerol, triglycidyl ether of trimethylolpropane, tetraepoxy of sorbitol Propyl ether, hexaglycidyl ether of dipentaerythritol, diglycidyl ether of polyethylene glycol, diglycidyl ether of polypropylene glycol, dicyclopentadiene dimethanol diglycidyl ether, etc. Propylene oxide, and combining one or more types of alkylene oxide with propylene glycol, trimethylol propylene Polyglycidyl etherate of polyether polyol and diglycidyl ester of aliphatic long-chain dibasic acid obtained by addition of aliphatic polyols such as alkane and glycerol.
多元醇之環氧丙基化物、或多元醇環氧烷加成物之環氧丙基化物(A1),進一步可列舉脂肪族高級醇之單環氧丙醚或高級脂肪酸之環氧丙基酯、環氧化大豆油、環氧基硬脂酸辛酯、環氧基硬脂酸丁酯、環氧化大豆油、環氧化聚丁二烯等。 The glycidyl compound of polyhydric alcohol, or the glycidyl compound of polyhydric alcohol alkylene oxide adduct (A1), further examples include the monoglycidyl ether of aliphatic higher alcohol or the glycidyl ester of higher fatty acid , Epoxidized soybean oil, epoxy octyl stearate, epoxy butyl stearate, epoxidized soybean oil, epoxidized polybutadiene, etc.
分子量200以上之多元醇的環氧丙基化物、或多元醇環氧烷加成物的環氧丙基化物(A1)係含有飽和縮合環者,可提高硬化物之硬化性及密著性,故較佳。 The glycidyl product of a polyol with a molecular weight of 200 or more, or the glycidyl product of a polyol alkylene oxide adduct (A1) contains saturated condensed rings, which can improve the hardenability and adhesion of the cured product. So better.
上述分子量200以上之多元醇的環氧丙基化物、或多元醇環氧烷加成物的環氧丙基化物(A1)可使用市售品,可列舉例如DenacolEX-121、DenacolEX-171、DenacolEX-192、DenacolEX-211、DenacolEX-212、DenacolEX-313、DenacolEX-314、DenacolEX-321、DenacolEX-411、DenacolEX-421、DenacolEX-512、DenacolEX-521、DenacolEX-611、DenacolEX-612、DenacolEX-614、DenacolEX-622、DenacolEX-810、DenacolEX-811、DenacolEX-850、DenacolEX-851、DenacolEX-821、DenacolEX-830、DenacolEX-832、DenacolEX-841、DenacolEX-861、DenacolEX-911、DenacolEX-941、DenacolEX-920、DenacolEX-931(nagasechemtex(股)公司製);Epolite M-1230、Epolite 40E、Epolite100E、Epolite 200E、Epolite400E、 Epolite70P、Epolite200P、Epolite400P、Epolite1500NP、Epolite1600、Epolite80MF、Epolite100MF(共榮社化學(股)公司製)、ADEKA GLYCIROL ED-503、ADEKA GLYCIROL ED-503G、ADEKA GLYCIROL ED-506、ADEKA GLYCIROL ED-523T、ADEKA RESIN EP-4088S、ADEKA RESIN EP-4080E((股)ADEKA公司製)等。 Commercially available products can be used for the glycidyl product of a polyol having a molecular weight of 200 or more or the glycidyl product (A1) of a polyol alkylene oxide adduct. Examples include DenacolEX-121, DenacolEX-171, DenacolEX -192, DenacolEX-211, DenacolEX-212, DenacolEX-313, DenacolEX-314, DenacolEX-321, DenacolEX-411, DenacolEX-421, DenacolEX-512, DenacolEX-521, DenacolEX-611, DenacolEX-612, DenacolEX-614 , DenacolEX-622, DenacolEX-810, DenacolEX-811, DenacolEX-850, DenacolEX-851, DenacolEX-821, DenacolEX-830, DenacolEX-832, DenacolEX-841, DenacolEX-861, DenacolEX-911, DenacolEX-941, DenacolEX -920, DenacolEX-931 (manufactured by nagasechemtex (stock) company); Epolite M-1230, Epolite 40E, Epolite 100E, Epolite 200E, Epolite 400E, Epolite70P, Epolite200P, Epolite400P, Epolite1500NP, Epolite1600, Epolite80MF, Epolite100MF (manufactured by Kyoeisha Chemical Co., Ltd.), ADEKA GLYCIROL ED-503, ADEKA GLYCIROL ED-503G, ADEKA GLYCIROL ED-506, ADEKA GLYCIRED-523T, ADEKA GLYCIROL ADEKA GLYCIROL RESIN EP-4088S, ADEKA RESIN EP-4080E (made by ADEKA Corporation), etc.
上述氧雜環丁烷化合物(A2)可列舉3,7-雙(3-氧環丁基)-5-氧雜-壬烷、1,4-雙[(3-乙基-3-氧環丁基甲氧基)甲基]苯、1,2-雙[(3-乙基-3-氧環丁基甲氧基)甲基]乙烷、1,3-雙[(3-乙基-3-氧環丁基甲氧基)甲基]丙烷、乙二醇雙(3-乙基-3-氧環丁基甲基)醚、三乙二醇雙(3-乙基-3-氧環丁基甲基)醚、四乙二醇雙(3-乙基-3-氧環丁基甲基)醚、1,4-雙(3-乙基-3-氧環丁基甲氧基)丁烷、1,6-雙(3-乙基-3-氧環丁基甲氧基)己烷等之二官能脂肪族氧雜環丁烷化合物、3-乙基-3-[(苯氧基)甲基]氧雜環丁烷、3-乙基-3-(己氧基甲基)氧雜環丁烷、3-乙基-3-(2-乙基己氧基甲基)氧雜環丁烷、3-乙基-3-(羥基甲基)氧雜環丁烷、3-乙基-3-(氯甲基)氧雜環丁烷等之一官能氧雜環丁烷化合物等。此等可1種單獨使用或組合2種以上使用。上述氧雜環丁烷化合物(A2)之中,多官能性氧雜環丁烷化合物因硬化物之玻璃轉移溫度高,故較佳。 The above-mentioned oxetane compound (A2) includes 3,7-bis(3-oxocyclobutyl)-5-oxa-nonane, 1,4-bis[(3-ethyl-3-oxo Butylmethoxy)methyl]benzene, 1,2-bis[(3-ethyl-3-oxocyclobutylmethoxy)methyl]ethane, 1,3-bis[(3-ethyl-3-oxy Cyclobutyl methoxy) methyl) propane, ethylene glycol bis (3-ethyl-3-oxocyclobutyl methyl) ether, triethylene glycol bis (3-ethyl-3-oxocyclobutyl methyl) ether, four Ethylene glycol bis(3-ethyl-3-oxocyclobutylmethyl)ether, 1,4-bis(3-ethyl-3-oxobutylmethoxy)butane, 1,6-bis(3-ethyl Difunctional aliphatic oxetane compounds such as oxy-3-oxocyclobutylmethoxy) hexane, 3-ethyl-3-[(phenoxy)methyl]oxetane, 3-ethyl 3-(hexyloxymethyl)oxetane, 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-(hydroxyl Monofunctional oxetane compounds such as methyl)oxetane and 3-ethyl-3-(chloromethyl)oxetane. These can be used individually by 1 type or in combination of 2 or more types. Among the above-mentioned oxetane compounds (A2), the polyfunctional oxetane compound is preferable because the glass transition temperature of the cured product is high.
上述氧雜環丁烷化合物(A2)可使用市售品,可列舉例如2-羥基乙基乙烯醚、二乙二醇單乙烯醚、 4-羥基丁基乙烯醚(丸善石油化學(股)公司製);ARON OXETANE OXT-121、OXT-221、EXOH、POX、OXA、OXT-101、OXT-211、OXT-212(東亞合成(股)公司製)、ETERNACOLL OXBP、OXTP(宇部興產(股)公司製)等。 Commercial products can be used for the oxetane compound (A2), and examples include 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, 4-Hydroxybutyl vinyl ether (manufactured by Maruzen Petrochemical Co., Ltd.); ARON OXETANE OXT-121, OXT-221, EXOH, POX, OXA, OXT-101, OXT-211, OXT-212 (Tohya Synthetic Co., Ltd.) ) Company system), ETERNACOLL OXBP, OXTP (Ube Industries Co., Ltd. system), etc.
上述脂環式環氧化合物(A3)係指環氧乙烷環不經由鍵結基而直接鍵結於飽和環者。脂環式環氧化合物(A3)之具體例,可列舉藉由將具有至少1個脂環式環之多元醇的聚環氧丙醚化物或含有環己烯或環戊烯環之化合物以氧化劑進行環氧化所得的含有環己烯氧化物或環戊烯氧化物的化合物。可列舉例如3,4-環氧基環己基甲基-3,4-環氧基環己烷羧酸酯、3,4-環氧基-1-甲基環己基-3,4-環氧基-1-甲基己烷羧酸酯、6-甲基-3,4-環氧基環己基甲基-6-甲基-3,4-環氧基環己烷羧酸酯、3,4-環氧基-3-甲基環己基甲基-3,4-環氧基-3-甲基環己烷羧酸酯、3,4-環氧基-5-甲基環己基甲基-3,4-環氧基-5-甲基環己烷羧酸酯、雙(3,4-環氧基環己基甲基)己二酸酯、3,4-環氧基-6-甲基環己烷羧酸酯、亞甲基雙(3,4-環氧基環己烷)、丙烷-2,2-二基-雙(3,4-環氧基環己烷)、2,2-雙(3,4-環氧基環己基)丙烷、二環戊二烯二環氧化物、伸乙基雙(3,4-環氧基環己烷羧酸酯)、環氧基六氫鄰苯二甲酸二辛酯、環氧基六氫鄰苯二甲酸二-2-乙基己酯、1-環氧基乙基-3,4-環氧基環己烷、1,2-環氧基-2-環氧基乙基環己烷、α-蒎烯氧化物、檸檬烯二氧化物等。脂環式環氧化合物(A3)從提 高密著性的觀點,較佳為3,4-環氧基環己基甲基-3,4-環氧基環己烷羧酸酯或3,4-環氧基-1-甲基環己基-3,4-環氧基-1-甲基己烷羧酸酯。 The above-mentioned alicyclic epoxy compound (A3) means that the ethylene oxide ring is directly bonded to a saturated ring without a bonding group. Specific examples of the alicyclic epoxy compound (A3) can be exemplified by using a polyglycidide etherate of a polyol having at least one alicyclic ring or a compound containing a cyclohexene or cyclopentene ring with an oxidizing agent Cyclohexene oxide or cyclopentene oxide-containing compound obtained by epoxidation. Examples include 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy -1-methylhexane carboxylate, 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexane carboxylate, 3, 4-Epoxy-3-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexane carboxylate, 3,4-epoxy-5-methylcyclohexylmethyl -3,4-Epoxy-5-methylcyclohexanecarboxylate, bis(3,4-epoxycyclohexylmethyl)adipate, 3,4-epoxy-6-methyl Cyclohexane carboxylate, methylene bis(3,4-epoxycyclohexane), propane-2,2-diyl-bis(3,4-epoxycyclohexane), 2, 2-bis(3,4-epoxycyclohexyl)propane, dicyclopentadiene diepoxide, ethylenebis(3,4-epoxycyclohexane carboxylate), epoxy six Dioctyl hydrogen phthalate, di-2-ethylhexyl epoxy hexahydrophthalate, 1-epoxyethyl-3,4-epoxycyclohexane, 1,2- Epoxy-2-epoxyethylcyclohexane, α-pinene oxide, limonene dioxide, etc. Alicyclic epoxy compound (A3) from the From the viewpoint of high adhesion, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate or 3,4-epoxy-1-methylcyclohexyl- 3,4-Epoxy-1-methylhexane carboxylate.
上述脂環式環氧化合物(A3)可使用市售品,可列舉例如CELLOXID2021P、CELLOXID2081、CELLOXID2000、CELLOXID3000((股)DAICEL公司製)等。 Commercial products can be used for the alicyclic epoxy compound (A3), and examples thereof include CELLOXID2021P, CELLOXID2081, CELLOXID2000, and CELLOXID3000 (manufactured by DAICEL Corporation).
上述芳香族環氧化合物(A4)係指含有芳香環的環氧化合物,而芳香族環氧化合物(A4)之具體例,可列舉酚、甲酚、丁酚等具有至少1個芳香族環的多元酚或、其環氧烷加成物之單/聚環氧丙醚化物,可列舉例如雙酚A、雙酚F、或此等再加成環氧烷之化合物之環氧丙醚化物或環氧基酚醛清漆樹脂;間苯二酚或氫醌、兒茶酚等之具有2個以上之酚性羥基的芳香族化合物之單/聚環氧丙醚化物;苯基二甲醇或苯基二乙醇、苯基二丁醇等之具有2個以上之醇性羥基之芳香族化合物之環氧丙醚化物;苯二甲酸、對苯二甲酸、偏苯三甲酸等之具有2個以上之羧酸的多元酸芳香族化合物之環氧丙基酯、苯甲酸之環氧丙基酯、苯乙烯氧化物或二乙烯基苯之環氧化物等。 The above-mentioned aromatic epoxy compound (A4) refers to an epoxy compound containing an aromatic ring, and specific examples of the aromatic epoxy compound (A4) include those having at least one aromatic ring such as phenol, cresol, and butylphenol. Polyhydric phenol or its alkylene oxide adduct mono/polypropylene etherate, for example, bisphenol A, bisphenol F, or the glycidyl etherate of these compounds added with alkylene oxide or Epoxy novolac resin; mono/polyglycidyl etherate of aromatic compounds with two or more phenolic hydroxyl groups such as resorcinol, hydroquinone, catechol, etc.; phenyl dimethanol or phenyl dimethanol Glycidyl etherate of aromatic compounds with two or more alcoholic hydroxyl groups such as ethanol and phenyl dibutanol; carboxylic acids with two or more phthalic acid, terephthalic acid, trimellitic acid, etc. The glycidyl ester of the polybasic acid aromatic compound, the glycidyl ester of benzoic acid, the styrene oxide or the epoxide of divinylbenzene, etc.
上述芳香族環氧化合物(A4)可使用市售品,可列舉例如DenacolEX-146、DenacolEX-147、DenacolEX-201、DenacolEX-203、DenacolEX-711、DenacolEX-721、On Court EX-1020、On Court EX-1030、On Court EX-1040、On Court EX-1050、On Court EX- 1051、On Court EX-1010、On Court EX-1011、On Court 1012(nagase chemtex(股)公司製);OGSOL PG-100、OGSOL EG-200、OGSOLEG-210、OGSOL EG-250(大阪氣體化學(股)公司製);HP4032、HP4032D、HP4700(DIC(股)公司製);ESN-475V(新日鐵住金化學(股)公司製);EpikoteYX8800(三菱化學(股)公司製);Marproof G-0105SA、Marproof G-0130SP(日油(股)公司製);EPICLONN-665、EPICLONHP-7200(DIC(股)公司製);EOCN-1020、EOCN-102S、EOCN-103S、EOCN-104S、XD-1000、NC-3000、EPPN-501H、EPPN-501HY、EPPN-502H、NC-7000L(日本化藥(股)公司製);ADEKA RESIN EP-4000、ADEKA RESINEP-4005、ADEKA RESIN EP-4100、ADEKA RESIN EP-4901((股)ADEKA公司製);TECHMORE VG-3101L((股)Printec公司製)等。上述芳香族環氧化合物(A4)中,多官能者因硬化性優異,故較佳。 Commercial products can be used for the above-mentioned aromatic epoxy compound (A4), and examples thereof include DenacolEX-146, DenacolEX-147, DenacolEX-201, DenacolEX-203, DenacolEX-711, DenacolEX-721, On Court EX-1020, On Court EX-1030, On Court EX-1040, On Court EX-1050, On Court EX- 1051, On Court EX-1010, On Court EX-1011, On Court 1012 (manufactured by Nagase Chemtex Co., Ltd.); OGSOL PG-100, OGSOL EG-200, OGSOLEG-210, OGSOL EG-250 (Osaka Gas Chemical Co., Ltd.) (Shares) company); HP4032, HP4032D, HP4700 (manufactured by DIC Corporation); ESN-475V (manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.); Epikote YX8800 (manufactured by Mitsubishi Chemical Corporation); Marproof G- 0105SA, Marproof G-0130SP (manufactured by NOF Corporation); EPICLONN-665, EPICLONHP-7200 (manufactured by DIC Corporation); EOCN-1020, EOCN-102S, EOCN-103S, EOCN-104S, XD- 1000, NC-3000, EPPN-501H, EPPN-501HY, EPPN-502H, NC-7000L (manufactured by Nippon Kayaku Co., Ltd.); ADEKA RESIN EP-4000, ADEKA RESINEP-4005, ADEKA RESIN EP-4100, ADEKA RESIN EP-4901 (made by ADEKA Corporation); TECHMORE VG-3101L (made by Printec Corporation), etc. Among the above-mentioned aromatic epoxy compounds (A4), polyfunctional ones are preferred because they are excellent in curability.
上述乙烯醚化合物可列舉例如二乙二醇單乙烯醚、三乙二醇二乙烯醚、n-十二烷基乙烯醚、環己基乙烯醚、2-乙基己基乙烯醚、2-氯乙基乙烯醚、乙基乙烯醚、異丁基乙烯醚、三乙二醇乙烯醚、2-羥基乙基乙烯醚、4-羥基丁基乙烯醚、1,6-環己烷二甲醇單乙烯醚、乙二醇二乙烯醚、1,4-丁二醇二乙烯醚、1,6-環己烷二甲醇二乙烯醚等。 The vinyl ether compound includes, for example, diethylene glycol monovinyl ether, triethylene glycol divinyl ether, n-dodecyl vinyl ether, cyclohexyl vinyl ether, 2-ethylhexyl vinyl ether, 2-chloroethyl Vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, triethylene glycol vinyl ether, 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, 1,6-cyclohexanedimethanol monovinyl ether, Ethylene glycol divinyl ether, 1,4-butanediol divinyl ether, 1,6-cyclohexanedimethanol divinyl ether, etc.
上述陽離子聚合性成分(A)中,上述分子量 200以上之多元醇的環氧丙基化物、或多元醇環氧烷加成物之環氧丙基化物(A1)、氧雜環丁烷化合物(A2)、脂環式環氧化合物(A3)、芳香族環氧化合物(A4)及乙烯醚化合物之使用比例係相對於陽離子聚合性成分(A)100質量份時,分子量200以上之多元醇的環氧丙基化物、或多元醇環氧烷加成物之環氧丙基化物(A1)40~70質量份、氧雜環丁烷化合物(A2)30~60質量份、脂環式環氧化合物(A3)0~50質量份、芳香族環氧化合物(A4)0~30質量份、乙烯醚化合物0~20質量份,可提高黏度、塗佈性、反應性及硬化性,故較佳。 In the above-mentioned cationically polymerizable component (A), the above-mentioned molecular weight Epoxy propyl compound of polyhydric alcohol of 200 or more, or glycidyl compound of polyhydric alcohol alkylene oxide adduct (A1), oxetane compound (A2), alicyclic epoxy compound (A3) , The use ratio of aromatic epoxy compound (A4) and vinyl ether compound is based on 100 parts by mass of the cationically polymerizable component (A), the epoxy propyl compound of the polyol with a molecular weight of 200 or more, or the polyol alkylene oxide The epoxy propyl compound (A1) of the adduct (A1) 40~70 mass parts, the oxetane compound (A2) 30~60 mass parts, the alicyclic epoxy compound (A3) 0~50 mass parts, aromatic The epoxy compound (A4) 0-30 parts by mass and the vinyl ether compound 0-20 parts by mass are preferred because they can improve viscosity, coatability, reactivity, and curability.
本發明之硬化性組成物的陽離子聚合起始劑(B)係指藉由能量線照射或加熱可釋放使陽離子聚合開始之物質的化合物時,皆可使用,較佳為藉由能量線照射釋放出路易斯酸之鎓鹽的複鹽或其衍生物。此化合物之代表性者,可列舉下述通式、[A]r+[B]r-表示之陽離子與陰離子的鹽。 The cationic polymerization initiator (B) of the curable composition of the present invention refers to a compound that can release a substance that initiates cationic polymerization by energy ray irradiation or heating. It can be used, and it is preferably released by energy ray irradiation. The double salt of the onium salt of Lewis acid or its derivative. Representatives of this compound include salts of cations and anions represented by the following general formula, [A] r+ [B] r-.
此處,陽離子[A]r+較佳為鎓類,其構造例如可以下述通式[(R2)aQ]r+表示。 Here, the cation [A] r+ is preferably an onium, and its structure can be represented by the following general formula [(R 2 ) a Q] r+, for example.
再者,此處,R2係碳原子數為1~60,且可含有幾個碳原子以外之原子的有機基。a為1~5之整數。a個之R2可各自獨立為相同或相異。又,至少1個為具有芳香 環之如上述的有機基為佳。Q為選自由S、N、Se、Te、P、As、Sb、Bi、O、I、Br、Cl、F、N=N所成群之原子或原子團。又,陽離子[A]r+中之Q的原子價為q時,r=a-q之關係(惟,N=N視為原子價0)必須成立。 In addition, here, R 2 is an organic group having 1 to 60 carbon atoms and may contain several atoms other than carbon atoms. a is an integer from 1 to 5. R 2 of a can be the same or different independently. In addition, at least one of them is preferably an organic group as described above having an aromatic ring. Q is an atom or group of atoms selected from the group consisting of S, N, Se, Te, P, As, Sb, Bi, O, I, Br, Cl, F, N=N. Moreover, when the valence of Q in the cation [A] r+ is q, the relationship of r=aq (but N=N is regarded as the valence 0) must be established.
又,陰離子[B]r-較佳為鹵化物錯合物,其構造例如可以下述通式[LYb]r-表示。 In addition, the anion [B] r- is preferably a halide complex, and its structure can be represented by the following general formula [LY b ] r-, for example.
此外,在此,L為鹵化物錯合物之中心原子的金屬或半金屬(Metalloid),其係B、P、As、Sb、Fe、Sn、Bi、Al、Ca、In、Ti、Zn、Sc、V、Cr、Mn、Co等。Y為鹵素原子。b為3~7之整數。又,陰離子[B]r-中之L的原子價當作p時,r=b-p之關係必須成立。 In addition, here, L is the metal or semimetal (Metalloid) of the central atom of the halide complex, which is B, P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, V, Cr, Mn, Co, etc. Y is a halogen atom. b is an integer of 3-7. In addition, when the valence of L in the anion [B] r- is regarded as p, the relationship r=bp must be established.
上述通式之陰離子[LYb]r-的具體例,可列舉肆(五氟苯基)硼酸根、四(3,5-二氟-4-甲氧基苯基)硼酸根、四氟硼酸根(BF4)-、六氟磷酸根(PF6)-、六氟銻酸根(SbF6)-、六氟砷酸根(AsF6)-、六氯銻酸根(SbCl6)-等。 Specific examples of the anion [LY b ] r- of the above general formula include tetrakis (pentafluorophenyl) borate, tetrakis (3,5-difluoro-4-methoxyphenyl) borate, and tetrafluoroboric acid root (BF 4) -, hexafluorophosphate (PF 6) -, hexafluoroantimonate (SbF 6) -, hexafluoroarsenate (AsF 6) -, hexachloro antimonate (SbCl 6) - and the like.
又,陰離子[B]r-亦可使用下述通式[LYb-1(OH)]r-表示之構造者。L、Y、b係與上述相同。又,其他可使用之陰離子,可列舉過氯酸離子(ClO4)-、三氟甲基亞硫酸離子(CF3SO3)-、氟磺酸離子(FSO3)-、甲苯磺酸陰離子、三硝基苯磺酸陰離子、樟腦磺酸根、九氟丁烷磺酸根、十六氟辛烷磺酸根、四芳基硼酸根、肆(五氟苯基)硼酸根 等。 In addition, as the anion [B] r- , a structure represented by the following general formula [LY b-1 (OH)] r- may also be used. L, Y, and b are the same as above. In addition, other usable anions include perchlorate ion (ClO 4 ) - , trifluoromethyl sulfite ion (CF 3 SO 3 ) - , fluorosulfonic acid ion (FSO 3 ) - , toluenesulfonic acid anion, Trinitrobenzene sulfonate anion, camphor sulfonate, nonafluorobutane sulfonate, hexafluorooctane sulfonate, tetraaryl borate, tetrakis (pentafluorophenyl) borate, etc.
本發明之硬化性組成物中,如此鎓鹽之中,以使用下述(甲)~(丙)之芳香族鎓鹽特別有效。可由此等之中以1種單獨使用或混合2種以上使用。 In the curable composition of the present invention, among such onium salts, it is particularly effective to use the following aromatic onium salts (A) to (C). Among these, 1 type can be used individually or in mixture of 2 or more types.
(甲)苯基重氮鎓六氟磷酸鹽、4-甲氧基苯基重氮鎓六氟銻酸鹽、4-甲基苯基重氮鎓六氟磷酸鹽等之芳基重氮鎓鹽 (A) Phenyldiazonium hexafluorophosphate, 4-methoxyphenyldiazonium hexafluoroantimonate, 4-methylphenyldiazonium hexafluorophosphate and other aryl diazonium salts
(乙)二苯基錪六氟銻酸鹽、二(4-甲基苯基)錪六氟磷酸鹽、二(4-tert-丁基苯基)錪六氟磷酸鹽、甲苯基異丙苯基錪肆(五氟苯基)硼酸鹽等之二芳基錪鹽 (B) Diphenyl hexafluoroantimonate, bis(4-methylphenyl) hexafluorophosphate, bis(4-tert-butylphenyl) hexafluorophosphate, tolylcumene Diaryl iodonium salts such as pentafluorophenyl borate
(丙)下述群I或群II表示之鋶陽離子與六氟銻離子、六氟磷酸根離子、肆(五氟苯基)硼酸根離子等之鋶鹽 (C) The following alumium cations represented by group I or group II and hexafluoroantimony ions, hexafluorophosphate ions, tetrakis (pentafluorophenyl) borate ions, etc.
<群I>
<群II>
又,其他較佳者可列舉(η5-2,4-環戊二烯-1-基)[(1,2,3,4,5,6-η)-(1-甲基乙基)苯〕-鐵-六氟磷酸鹽等之鐵-芳烴錯合物、或參(乙醯丙酮)鋁、參(乙醯乙酸乙酯)鋁、參(水楊醛)鋁等之鋁錯合物與三苯基矽烷醇等之矽烷醇類的混合物;噻吩鎓鹽、四氫噻吩鐵鹽(thiolanium)、苄基銨、吡啶鎓鹽、鉼鹽(hydrazinium)等之鹽;二乙烯三胺、三乙烯三胺、四乙烯五胺等之聚烷基多胺類;1,2-二胺基環己烷、1,4-二胺基-3,6-二乙基環己烷、異佛爾酮二胺等之脂環式多胺類;m-苯二甲胺、二胺基二苯基甲烷、二胺基二苯基碸等之芳香族多胺類;藉由一般方法使上述多胺類與苯基環氧丙醚、丁基環氧丙醚、雙酚A-二環氧丙醚、雙酚F-二環氧丙 醚等之環氧丙醚類或羧酸之環氧丙基酯類等的各種環氧樹脂反應所製造的聚環氧基加成改質物;藉由一般方法使上述有機多胺類與鄰苯二甲酸、間苯二甲酸、二聚酸等之羧酸類反應所製造的醯胺化改質物;藉由一般方法使上述多胺類與甲醛等之醛類及酚、甲酚、二甲酚、第三丁基酚、間苯二酚等之於核具有至少一個醛化反應性場所的酚類反應所製造的曼尼希(Mannich)化改質物;多元羧酸(草酸、丙二酸、琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、十二烷二酸、2-甲基琥珀酸、2-甲基己二酸、3-甲基己二酸、3-甲基戊二酸、2-甲基辛二酸、3,8-二甲基癸二酸、3,7-二甲基癸二酸、氫化二聚酸、二聚酸等之脂肪族二羧酸類;鄰苯二甲酸、對苯二甲酸、間苯二甲酸、萘二羧酸等之芳香族二羧酸類;環己烷二羧酸等之脂環式二羧酸類;偏苯三甲酸、均苯三甲酸(Trimesic Acid)、蓖麻油脂肪酸之三聚物等之三羧酸類;均苯四酸等之四羧酸類等)之酸酐;雙氰胺、咪唑類、羧酸酯、磺酸酯、胺醯亞胺等。 Moreover, other preferable ones include (η 5 -2,4-cyclopentadien-1-yl) [(1,2,3,4,5,6-η)-(1-methylethyl) Benzene]-iron-hexafluorophosphate and other iron-arene complexes, or ginseng (acetone) aluminum, ginseng (acetate ethyl) aluminum, ginseng (salicylic aldehyde) aluminum and other aluminum complexes Mixtures with silanols such as triphenylsilanol; thiophenium salt, thiolanium, benzylammonium, pyridinium salt, hydrazinium salt, etc.; diethylenetriamine, tris Polyalkyl polyamines such as ethylene triamine and tetraethylene pentamine; 1,2-diaminocyclohexane, 1,4-diamino-3,6-diethylcyclohexane, isophor Alicyclic polyamines such as ketonediamines; aromatic polyamines such as m-xylylenediamine, diaminodiphenylmethane, diaminodiphenylmethane, etc.; the above-mentioned polyamines are made by general methods Glycidyl ethers such as phenyl glycidyl ether, butyl glycidyl ether, bisphenol A-diglycidyl ether, bisphenol F-diglycidyl ether, etc. or glycidyl of carboxylic acid Polyepoxy adduct modified products produced by the reaction of various epoxy resins such as esters; the above-mentioned organic polyamines are reacted with carboxylic acids such as phthalic acid, isophthalic acid, and dimer acid by a general method The manufactured amide modified product; the above-mentioned polyamines, formaldehyde and other aldehydes, phenols, cresols, xylenol, tertiary butylphenol, resorcinol, etc. have at least Mannich modified product produced by phenolic reaction in a reactive site of aldehyde; polycarboxylic acid (oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid) Acid, azelaic acid, sebacic acid, dodecanedioic acid, 2-methylsuccinic acid, 2-methyladipic acid, 3-methyladipic acid, 3-methylglutaric acid, 2-methyl Aliphatic dicarboxylic acids such as suberic acid, 3,8-dimethyl sebacic acid, 3,7-dimethyl sebacic acid, hydrogenated dimer acid, dimer acid; phthalic acid, terephthalic acid Aromatic dicarboxylic acids such as dicarboxylic acid, isophthalic acid and naphthalenedicarboxylic acid; alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid; trimellitic acid, trimesic acid, castor Tricarboxylic acids such as trimers of sesame oil fatty acids; tetracarboxylic acids such as pyromellitic acid, etc.) anhydrides; dicyandiamide, imidazoles, carboxylic acid esters, sulfonate esters, amine imides, etc.
此等之中,就實用面與提高光感度的觀點,使用芳香族錪鹽、芳香族鋶鹽、鐵-芳烴錯合物為佳;相對於陽離子聚合起始劑(B)100質量%,又更佳為含有至少0.1質量%以上之具有下述構造之芳香族鋶鹽。 Among these, from the viewpoint of practicality and improvement of photosensitivity, it is preferable to use aromatic iodonium salt, aromatic sulphur salt, iron-arene complex; relative to 100% by mass of cationic polymerization initiator (B), and More preferably, it contains at least 0.1% by mass or more of an aromatic sulfonium salt having the following structure.
此處,式中,R11、R12、R13、R14、R15、R16、R17、R18、R19及R20各自獨立地表示氫原子、鹵素原子、碳原子數1~10之烷基、碳原子數1~10之烷氧基或碳原子數2~10之酯基,R21、R22、R23及R24各自獨立地表示氫原子、鹵素原子或碳原子數1~10之烷基,R25表示氫原子、鹵素原子、碳原子數1~10之烷基或選自下述化學式(A)~(C)中的任一取代基,Anq-表示q價的陰離子,p表示使電荷為中性的係數。 Here, in the formula, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 each independently represent a hydrogen atom, a halogen atom, and the number of carbon atoms from 1 to 10 alkyl group, C 1-10 alkoxy group or C 2-10 ester group, R 21 , R 22 , R 23 and R 24 each independently represent a hydrogen atom, a halogen atom or the number of carbon atoms An alkyl group of 1 to 10, R 25 represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 10 carbon atoms, or any substituent selected from the following chemical formulas (A) to (C), An q- represents q For a valence anion, p represents a coefficient that makes the charge neutral.
此處,式中,R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23、R24、R26、R27、R28、R29、R35、R36、R37、R38及R39各自獨立地表示氫原子、鹵素原子、碳原子數1~10之烷基、碳原子數1~10之烷氧基或 碳原子數2~10之酯基,R30、R31、R32、R33及R34各自獨立地表示氫原子、鹵素原子或碳原子數1~10之烷基。 Here, in the formula, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 26 , R 27 , R 28 , R 29 , R 35 , R 36 , R 37 , R 38 and R 39 each independently represent a hydrogen atom, a halogen atom, an alkyl group with 1 to 10 carbon atoms, and 1 to 10 carbon atoms R 30 , R 31 , R 32 , R 33 and R 34 each independently represent a hydrogen atom, a halogen atom or an alkyl group with 1 to 10 carbon atoms.
上述通式(1)表示之化合物中,R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23、R24、R25、R26、R27、R28、R29、R30、R31、R32、R33、R34、R35、R36、R37、R38及R39表示之鹵素原子,可列舉氟、氯、溴、碘等。 In the compound represented by the above general formula (1), R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , Halogen represented by R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 and R 39 Examples of the atom include fluorine, chlorine, bromine, and iodine.
R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23、R24、R25、R26、R27、R28、R29、R30、R31、R32、R33、R34、R35、R36、R37、R38及R39表示之碳原子數1~10之烷基,可列舉甲基、乙基、丙基、異丙基、丁基、s-丁基、t-丁基、異丁基、戊基、異戊基、t-戊基、己基、環己基、庚基、辛基、壬基、乙基辛基、2-甲氧基乙基、3-甲氧基丙基、4-甲氧基丁基、2-丁氧基乙基、甲氧基乙氧基乙基、甲氧基乙氧基乙氧基乙基、3-甲氧基丁基、2-甲硫基乙基、氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、溴甲基、二溴甲基、三溴甲基、二氟乙基、三氯乙基、二氯二氟乙基、五氟乙基、七氟丙基、九氟丁基、十氟戊基、十三氟己基、十五氟庚基、十七氟辛基、甲氧基甲基、1,2-環氧基乙基、甲氧基乙基、甲氧基乙氧基甲基、甲硫基甲基、乙氧基乙基、丁氧基甲基、t-丁硫基甲基、4-戊烯氧基甲基、三氯乙氧基甲基、雙(2-氯乙氧基)甲基、甲氧基環己基、1-(2-氯乙氧基)乙基、1-甲基-1-甲氧基乙基、乙 基二硫乙基、三甲基甲矽烷基乙基、t-丁基二甲基甲矽烷氧基甲基、2-(三甲基甲矽烷基)乙氧基甲基、t-丁氧基羰基甲基、乙氧基羰基甲基、乙基羰基甲基、t-丁氧基羰基甲基、丙烯醯氧基乙基、甲基丙烯醯氧基乙基、2-甲基-2-金剛烷氧基羰基甲基、乙醯基乙基、2-甲氧基-1-丙烯基、羥基甲基、2-羥基乙基、1-羥基乙基、2-羥基丙基、3-羥基丙基、3-羥基丁基、4-羥基丁基、1,2-二羥基乙基等。 R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 and R 39 represent alkyl groups with 1 to 10 carbon atoms, including Methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl, isobutyl, pentyl, isopentyl, t-pentyl, hexyl, cyclohexyl, heptyl, Octyl, nonyl, ethyloctyl, 2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 2-butoxyethyl, methoxyethoxyethyl Group, methoxyethoxyethoxyethyl, 3-methoxybutyl, 2-methylthioethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloro Methyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, difluoroethyl, trichloroethyl, dichlorodifluoroethyl, pentafluoroethyl, heptafluoropropyl, nine Fluorobutyl, decafluoropentyl, tridecafluorohexyl, pentafluoroheptyl, heptafluorooctyl, methoxymethyl, 1,2-epoxyethyl, methoxyethyl, methoxy Ethoxymethyl, methylthiomethyl, ethoxyethyl, butoxymethyl, t-butylthiomethyl, 4-pentenoxymethyl, trichloroethoxymethyl, Bis(2-chloroethoxy)methyl, methoxycyclohexyl, 1-(2-chloroethoxy)ethyl, 1-methyl-1-methoxyethyl, ethyldithioethyl , Trimethylsilylethyl, t-butyldimethylsilyloxymethyl, 2-(trimethylsilyl)ethoxymethyl, t-butoxycarbonylmethyl, ethyl Oxycarbonylmethyl, ethylcarbonylmethyl, t-butoxycarbonylmethyl, acryloxyethyl, methacryloxyethyl, 2-methyl-2-adamantyloxycarbonylmethyl Group, acetoxyethyl, 2-methoxy-1-propenyl, hydroxymethyl, 2-hydroxyethyl, 1-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 3-hydroxy Butyl, 4-hydroxybutyl, 1,2-dihydroxyethyl, etc.
R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23、R24、R26、R27、R28、R29、R35、R36、R37、R38及R39表示之碳原子數1~10之烷氧基,可列舉甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、s-丁氧基、t-丁氧基、異丁氧基、戊氧基、異戊氧基、t-戊氧基、己氧基、環己氧基、環己基甲氧基、四氫呋喃氧基、四氫吡喃氧基、2-甲氧基乙氧基、3-甲氧基丙氧基、4-甲氧基丁氧基、2-丁氧基乙氧基、甲氧基乙氧基乙氧基、甲氧基乙氧基乙氧基乙氧基、3-甲氧基丁氧基、2-甲硫基乙氧基、三氟甲氧基等。 R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 26 , R 27 , R 28 , R 29 , R 35 , R 36 , R 37 , R 38 and R 39 represent alkoxy groups having 1 to 10 carbon atoms, including methoxy, ethoxy, propoxy, isopropoxy, Butoxy, s-butoxy, t-butoxy, isobutoxy, pentoxy, isopentoxy, t-pentoxy, hexyloxy, cyclohexyloxy, cyclohexylmethoxy , Tetrahydrofuranoxy, tetrahydropyranoxy, 2-methoxyethoxy, 3-methoxypropoxy, 4-methoxybutoxy, 2-butoxyethoxy, methoxy Group ethoxyethoxy, methoxyethoxyethoxyethoxy, 3-methoxybutoxy, 2-methylthioethoxy, trifluoromethoxy and the like.
R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23、R24、R26、R27、R28、R29、R35、R36、R37、R38及R39表示之碳原子數2~10之酯基,可列舉甲氧基羰基、乙氧基羰基、異丙氧基羰基、苯氧基羰基、乙醯氧基、丙醯氧基、丁醯氧基、氯乙醯氧基、二氯乙醯氧基、三氯乙醯氧基、三氟乙醯氧基、t-丁基羰氧 基、甲氧基乙醯氧基、苯甲醯氧基等。 R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 26 , R 27 , R 28 , R 29 , R 35 , R 36 , R 37 , R 38 and R 39 represent ester groups with 2 to 10 carbon atoms, including methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, and phenoxy Carbonyl, acetoxy, propoxy, butoxy, chloroacetoxy, dichloroacetoxy, trichloroacetoxy, trifluoroacetoxy, t-butylcarbonyl Oxy, methoxyacetoxy, benzyloxy and the like.
相對於陽離子聚合性成分(A)與自由基聚合性成分(C)與聚合物(E)與之合計100質量份,陽離子聚合起始劑(B)之使用比例為陽離子聚合起始劑(B)0.001~10質量份,較佳為0.1~10質量份。太少時,容易變得硬化不足,過多時,有時對於硬化物之吸水率或硬化物強度等之諸物性有不良影響的情形。 With respect to 100 parts by mass of the cationic polymerizable component (A), radical polymerizable component (C), and polymer (E) in total, the usage ratio of the cationic polymerization initiator (B) is the cationic polymerization initiator (B) ) 0.001-10 parts by mass, preferably 0.1-10 parts by mass. When it is too small, it is easy to become insufficiently hardened, and when it is too much, it may adversely affect various physical properties such as the water absorption rate and the strength of the hardened product.
本發明之硬化性組成物的自由基聚合性成分(C)係以具有環氧基及乙烯性不飽和基之化合物(C1)或碳原子數2~20之醇的丙烯酸酯或碳原子數2~20之醇的甲基丙烯酸酯(C2)為必須成分。 The radically polymerizable component (C) of the curable composition of the present invention is a compound having an epoxy group and an ethylenically unsaturated group (C1) or an acrylate of an alcohol having 2 to 20 carbon atoms or an acrylate having 2 to 20 carbon atoms. ~20 alcohol methacrylate (C2) is an essential ingredient.
上述具有環氧基及乙烯性不飽和基的化合物(C1),可列舉例如環氧基丙烯酸酯或環氧基甲基丙烯酸酯,具體而言,使以往公知之芳香族環氧樹脂、脂環式環氧樹脂、脂肪族環氧樹脂等與丙烯酸或甲基丙烯酸反應所得的丙烯酸酯。此等之環氧基丙烯酸酯或環氧基甲基丙烯酸酯之中,特佳為醇類之環氧丙醚的丙烯酸酯或甲基丙烯酸酯。 The compound (C1) having an epoxy group and an ethylenically unsaturated group includes, for example, epoxy acrylate or epoxy methacrylate, specifically, conventionally known aromatic epoxy resins and alicyclics Formula epoxy resin, aliphatic epoxy resin, etc., and acrylic acid or methacrylic acid reaction obtained acrylate. Among these epoxy acrylates or epoxy methacrylates, acrylate or methacrylate of glycidyl ether of alcohols is particularly preferred.
上述碳原子數2~20之醇的丙烯酸酯或碳原子數2~20之醇的甲基丙烯酸酯(C2),可列舉使分子中具有至少1個羥基的芳香族或脂肪族醇及其環氧烷加成物與丙烯酸或甲基丙烯酸反應所得的丙烯酸酯或甲基丙烯酸酯。具體而言,可列舉2-乙基己基丙烯酸酯、2-羥基乙基丙烯酸酯、2-羥基丙基丙烯酸酯、異戊基丙烯酸酯、月桂基丙 烯酸酯、十八烷基丙烯酸酯、異辛基丙烯酸酯、四氫糠基丙烯酸酯、異莰基丙烯酸酯、苄基丙烯酸酯、1,3-丁二醇二丙烯酸酯、1,4-丁二醇二丙烯酸酯、1,6-己二醇二丙烯酸酯、二乙二醇二丙烯酸酯、三乙二醇二丙烯酸酯、新戊二醇二丙烯酸酯、聚乙二醇二丙烯酸酯、聚丙二醇二丙烯酸酯、三羥甲基丙烷三丙烯酸酯、季戊四醇四丙烯酸酯、二季戊四醇六丙烯酸酯、ε-己內酯改質二季戊四醇六丙烯酸酯、2-乙基己基甲基丙烯酸酯、2-羥基乙基甲基丙烯酸酯、2-羥基丙基甲基丙烯酸酯、異戊基甲基丙烯酸酯、月桂基甲基丙烯酸酯、十八烷基甲基丙烯酸酯、異辛基甲基丙烯酸酯、四氫糠基甲基丙烯酸酯、異莰基甲基丙烯酸酯、苄基甲基丙烯酸酯、1,3-丁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、二乙二醇二甲基丙烯酸酯、三乙二醇二甲基丙烯酸酯、新戊二醇二甲基丙烯酸酯、聚乙二醇二甲基丙烯酸酯、聚丙二醇二甲基丙烯酸酯、三羥甲基丙烷三甲基丙烯酸酯、季戊四醇四甲基丙烯酸酯、二季戊四醇六甲基丙烯酸酯、ε-己內酯改質二季戊四醇六甲基丙烯酸酯等。又,此等之丙烯酸酯或甲基丙烯酸酯之中,特佳為多元醇之聚丙烯酸酯類或多元醇之聚甲基丙烯酸酯類。 The above-mentioned acrylates of alcohols with 2 to 20 carbon atoms or methacrylates (C2) of alcohols with 2 to 20 carbon atoms include aromatic or aliphatic alcohols having at least one hydroxyl group in the molecule and their rings Acrylate or methacrylate obtained by reacting an oxane adduct with acrylic acid or methacrylic acid. Specifically, 2-ethylhexyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, isoamyl acrylate, lauryl acrylate can be cited. Acrylate, octadecyl acrylate, isooctyl acrylate, tetrahydrofurfuryl acrylate, isobornyl acrylate, benzyl acrylate, 1,3-butanediol diacrylate, 1,4- Butylene glycol diacrylate, 1,6-hexanediol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, neopentyl glycol diacrylate, polyethylene glycol diacrylate, Polypropylene glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, ε-caprolactone modified dipentaerythritol hexaacrylate, 2-ethylhexyl methacrylate, 2 -Hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, isoamyl methacrylate, lauryl methacrylate, octadecyl methacrylate, isooctyl methacrylate , Tetrahydrofurfuryl methacrylate, isobornyl methacrylate, benzyl methacrylate, 1,3-butanediol dimethacrylate, 1,4-butanediol dimethacrylate , 1,6-Hexanediol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, neopentyl glycol dimethacrylate, polyethylene glycol dimethyl methacrylate Base acrylate, polypropylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, dipentaerythritol hexamethacrylate, ε-caprolactone modified dipentaerythritol hexamethyl Acrylic etc. Moreover, among these acrylates or methacrylates, polyacrylates of polyols or polymethacrylates of polyols are particularly preferred.
上述自由基聚合性成分(C)可使用(C1)或(C2)以外,藉由能量線照射或加熱活性化之自由基聚合起始劑,進行高分子化或交聯反應的化合物,可列舉例如烯丙基胺基甲酸酯化合物、不飽和聚酯化合物、苯乙烯系 化合物等。自由基聚合性成分(C)中之上述(C1)成分及(C2)成分的比例,較佳為50質量%以上。 The above-mentioned radical polymerizable component (C) can be a compound other than (C1) or (C2), which is activated by energy ray irradiation or heating, and undergoes polymerization or crosslinking reaction. Examples include Such as allyl carbamate compounds, unsaturated polyester compounds, styrene series Compound etc. The ratio of the above-mentioned (C1) component and (C2) component in the radically polymerizable component (C) is preferably 50% by mass or more.
本發明之硬化性組成物的自由基起始劑(D)無特別限制,可使用習知者。可使用例如苯乙酮系化合物、苄基系化合物、二苯甲酮系化合物、噻噸酮系化合物等之酮系化合物、肟系化合物等。 The radical initiator (D) of the curable composition of the present invention is not particularly limited, and conventional ones can be used. For example, ketone-based compounds such as acetophenone-based compounds, benzyl-based compounds, benzophenone-based compounds, and thioxanthone-based compounds, and oxime-based compounds can be used.
本發明之硬化性組成物的聚合物(E)係選自由上述式(I)表示之單體所得之聚合物、由上述式(II)表示之單體所得之聚合物、選自由上述式(I)表示之單體之二種以上之單體所得之聚合物、選自由上述式(II)表示之單體之二種以上之單體所得之聚合物及由上述式(I)表示之單體及上述式(II)表示之單體所得之聚合物所成群組,且重量平均分子量以聚苯乙烯換算為1,000~30,000。 The polymer (E) of the curable composition of the present invention is selected from a polymer obtained from the monomer represented by the above formula (I), a polymer obtained from the monomer represented by the above formula (II), and is selected from the above formula ( I) A polymer obtained from two or more monomers of the monomers represented by the above formula (II), a polymer obtained from two or more monomers selected from the monomers represented by the above formula (II), and the monomer represented by the above formula (I) The weight average molecular weight is 1,000 to 30,000 in terms of polystyrene, and the weight average molecular weight is a group of polymers obtained from the monomer and the monomer represented by the above formula (II).
上述式(I)中之X表示之碳原子數1~7之烷基,可列舉甲基、乙基、丙基、iso-丙基、丁基、sec-丁基、tert-丁基、iso-丁基、戊基、iso-戊基、tert-戊基、己基、2-己基、3-己基、環己基、4-甲基環己基、庚基、2-庚基、3-庚基、iso-庚基、tert-庚基等。此等之中,從硬化性的觀點,碳原子數1~4之烷基或以選自由環氧基、氧雜環丁烷基、羥基及羧基所成群組之1種以上之基進行部分取代之碳原子數1~4之烷基為佳。 The alkyl group having 1 to 7 carbon atoms represented by X in the above formula (I) includes methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso -Butyl, pentyl, iso-pentyl, tert-pentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, etc. Among these, from the viewpoint of curability, an alkyl group having 1 to 4 carbon atoms or one or more groups selected from the group consisting of epoxy group, oxetanyl group, hydroxy group and carboxyl group are partly used. The substituted alkyl group having 1 to 4 carbon atoms is preferred.
上述式(I)中之X表示之碳原子數1~7之烷氧基,可列舉甲氧基、乙氧基、丙氧基、iso-丙氧基、丁氧 基、sec-丁氧基、tert-丁氧基、iso-丁氧基、戊氧基、iso-戊氧基、tert-戊氧基、己氧基、2-己氧基、3-己氧基、環己氧基、4-甲基環己氧基、庚氧基、2-庚氧基、3-庚氧基、iso-庚氧基、tert-庚氧基等。此等之中,從硬化性的觀點,碳原子數1~4之烷氧基或以選自由環氧基、氧雜環丁烷基、羥基及羧基所成群組之1種以上之基進行部分取代之碳原子數1~4之烷氧基為佳。 The alkoxy group having 1 to 7 carbon atoms represented by X in the above formula (I) includes methoxy, ethoxy, propoxy, iso-propoxy, butoxy Group, sec-butoxy, tert-butoxy, iso-butoxy, pentoxy, iso-pentoxy, tert-pentoxy, hexyloxy, 2-hexoxy, 3-hexoxy Group, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2-heptyloxy, 3-heptyloxy, iso-heptyloxy, tert-heptyloxy, etc. Among these, from the standpoint of curability, an alkoxy group having 1 to 4 carbon atoms or one or more groups selected from the group consisting of an epoxy group, an oxetanyl group, a hydroxyl group, and a carboxyl group are used. Partially substituted alkoxy groups having 1 to 4 carbon atoms are preferred.
上述式(I)中之X表示之碳原子數6~12之芳基,可列舉苯基、甲基苯基、萘基等。 The aryl group having 6 to 12 carbon atoms represented by X in the above formula (I) includes a phenyl group, a methylphenyl group, and a naphthyl group.
上述式(I)中之X表示之碳原子數6~12之芳氧基,可列舉苯氧基、甲基苯氧基、萘氧基等。 The aryloxy group having 6 to 12 carbon atoms represented by X in the above formula (I) includes a phenoxy group, a methylphenoxy group, a naphthoxy group, and the like.
上述式(I)中之X表示之碳原子數6~10之脂環式烴基,可列舉環己基、甲基環己基、降莰基、雙環戊基、雙環辛基、三甲基雙環庚基、三環辛基、三環癸基、螺辛基、螺雙環戊基、金剛烷基、異莰基等。 The alicyclic hydrocarbon group with 6 to 10 carbon atoms represented by X in the above formula (I) includes cyclohexyl, methylcyclohexyl, norbornyl, dicyclopentyl, bicyclooctyl, and trimethylbicycloheptyl , Tricyclooctyl, tricyclodecyl, spirooctyl, spirobicyclopentyl, adamantyl, isobornyl, etc.
此等之烷基、烷氧基、芳基、芳氧基及脂環式烴基,可為此等之基中的氫原子經選自由環氧基、氧雜環丁烷基、羥基及羧基所成群之1種以上之基所取代。 These alkyl groups, alkoxy groups, aryl groups, aryloxy groups and alicyclic hydrocarbon groups can be selected from the group consisting of epoxy, oxetanyl, hydroxy and carboxyl groups. It is substituted by more than one group of groups.
上述式(I)中,X之一部分為經環氧基或氧雜環丁烷基取代時之式(I)表示的單體,可列舉例如下述式(1)~(3)表示之單體。 In the above formula (I), a part of X is a monomer represented by the formula (I) when it is substituted with an epoxy group or an oxetanyl group. Examples include the monomers represented by the following formulas (1) to (3) body.
在此,式(1)中,R3表示氫原子或碳原子數1~6之烷基,m為1~6之整數。 Here, in formula (1), R 3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and m is an integer of 1 to 6.
在此,式(2)中,R4表示氫原子或碳原子數1~6之烷基,n為1~6之整數。 Here, in formula (2), R 4 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n is an integer of 1 to 6.
在此,式(3)中,R5表示氫原子或碳原子數1~6之烷基,s為1~6之整數。 Here, in the formula (3), R 5 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and s is an integer of 1 to 6.
上述式(II)中,以R1所表示的鹵原子,可列舉氟、氯、溴、碘等。 In the above formula (II), the halogen atom represented by R 1 includes fluorine, chlorine, bromine, and iodine.
上述式(II)中,X’之碳原子數1~7之烷基、碳原子數6~12之芳基或碳原子數6~10之脂環式烴基,可列舉與上述式(I)同樣者。 In the above formula (II), the alkyl group with 1 to 7 carbon atoms, the aryl group with 6 to 12 carbon atoms or the alicyclic hydrocarbon group with 6 to 10 carbon atoms of X'can be exemplified by the above formula (I) Same thing.
上述式(II)中,X’之一部分經環氧基或氧雜環丁烷基取代時,作為式(II)所表示之單體,可列舉下述式(4)~(6)所表示者。 In the above formula (II), when a part of X'is substituted with an epoxy group or an oxetanyl group, the monomer represented by the formula (II) may be represented by the following formulas (4) to (6) By.
在此,式(4)中,R1係與上述式(II)相同,R6表示氫原子或碳原子數1~6之烷基,t為1~6之整數。 Here, in the formula (4), R 1 is the same as the above formula (II), R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and t is an integer of 1 to 6.
在此,式(5)中,R1係與上述式(II)相同,R7表示氫原子或碳原子數1~6之烷基,q為1~6之整數。 Here, in the formula (5), R 1 is the same as the above formula (II), R 7 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and q is an integer of 1 to 6.
在此,式(6)中,R1係與上述式(II)相同,R8表示氫原子或碳原子數1~6之烷基,y為1~6之整數。 Here, in the formula (6), R 1 is the same as the above formula (II), R 8 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and y is an integer of 1 to 6.
上述聚合物(E)中,構成聚合物之單體的使用比例係上述X為經選自由環氧基、環雜環丁烷基、羥基及羧基所成群之1種以上之基取代之碳原子數1~7之烷基、碳原子數6~12之芳基或碳原子數6~10之脂環式烴基時,使上述(I)或(II)表示之單體成為10~100質量%來使用,由於接著性提高,故較佳。 In the above-mentioned polymer (E), the usage ratio of the monomers constituting the polymer is that the above-mentioned X is a carbon substituted with one or more groups selected from the group consisting of epoxy, cyclobutanyl, hydroxyl, and carboxyl groups In the case of an alkyl group with 1 to 7 atoms, an aryl group with 6 to 12 carbon atoms, or an alicyclic hydrocarbon group with 6 to 10 carbon atoms, make the monomer represented by (I) or (II) above 10-100 mass % Is used, because the adhesion is improved, so it is better.
本發明之硬化性組成物中,相對於陽離子聚 合性成分(A)與自由基聚合性成分(C)與聚合物(E)之合計為100質量份,上述陽離子聚合性成分(A)為30~70質量份,上述陽離子聚合起始劑(B)為0.001~10質量份,上述自由基聚合性成分(C)為30~60質量份,上述自由基聚合起始劑(D)為1~10質量份,上述聚合物(E)為1~20質量份為佳。在上述調配比例以外時,硬化物之硬化性及密著性有變差的疑慮。 In the curable composition of the present invention, relative to cationic poly The total of the synthetic component (A), the radical polymerizable component (C), and the polymer (E) is 100 parts by mass, the cationic polymerizable component (A) is 30 to 70 parts by mass, and the cationic polymerization initiator ( B) is 0.001-10 parts by mass, the above-mentioned radical polymerizable component (C) is 30-60 parts by mass, the above-mentioned radical polymerization initiator (D) is 1-10 parts by mass, and the above-mentioned polymer (E) is 1 ~20 parts by mass is better. If the blending ratio is other than the above, the curability and adhesion of the cured product may be deteriorated.
本發明之硬化性組成物中,可依需要進一步使用增感劑及/或增感助劑。增感劑係於較陽離子聚合起始劑(B)所顯示之極大吸收波長更長的波長顯示極大吸收,促進藉由陽離子聚合起始劑(B)之聚合起始反應的化合物。又,增感助劑係更進一步促進增感劑之作用的化合物。 In the curable composition of the present invention, a sensitizer and/or a sensitizer auxiliary may be further used as needed. The sensitizer is a compound that exhibits maximum absorption at a wavelength longer than the maximum absorption wavelength shown by the cationic polymerization initiator (B), and promotes the polymerization initiation reaction by the cationic polymerization initiator (B). In addition, the sensitization aid is a compound that further promotes the action of the sensitizer.
增感劑及增感助劑可列舉蒽系化合物、萘系化合物等。 Examples of sensitizers and sensitization aids include anthracene-based compounds and naphthalene-based compounds.
蒽系化合物可列舉例如下述式(7)表示者。 Examples of the anthracene compound include those represented by the following formula (7).
此處,式(7)中,R50及R51各自獨立地表示氫原子、碳原子數1~6之烷基或碳原子數2~12之烷氧基烷基,R52表示氫原子或碳原子數1~6之烷基。 Here, in formula (7), R 50 and R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxyalkyl group having 2 to 12 carbon atoms, and R 52 represents a hydrogen atom or An alkyl group with 1 to 6 carbon atoms.
列舉上述式(7)表示之蒽系化合物之具體例時,有如以下的化合物。 When specific examples of the anthracene compound represented by the above formula (7) are given, there are the following compounds.
可列舉例如9,10-二甲氧基蒽、9,10-二乙氧基蒽、9,10-二丙氧基蒽、9,10-二異丙氧基蒽、9,10-二丁氧基蒽、9,10-二戊氧基蒽、9,10-二己氧基蒽、9,10-雙(2-甲氧基乙氧基)蒽、9,10-雙(2-乙氧基乙氧基)蒽、9,10-雙(2-丁氧基乙氧基)蒽、9,10-雙(3-丁氧基丙氧基)蒽、2-甲基-或2-乙基-9,10-二甲氧基蒽、2-甲基-或2-乙基-9,10-二乙氧基蒽、2-甲基-或2-乙基-9,10-二丙氧基蒽、2-甲基-或2-乙基-9,10-二異丙氧基蒽、2-甲基-或2-乙基-9,10-二丁氧基蒽、2-甲基-或2-乙基-9,10-二戊氧基蒽、2-甲基-或2-乙基-9,10-二己氧基蒽等。 Examples include 9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 9,10-dipropoxyanthracene, 9,10-diisopropoxyanthracene, 9,10-dibutyl Oxyanthracene, 9,10-dipentyloxyanthracene, 9,10-dihexoxyanthracene, 9,10-bis(2-methoxyethoxy)anthracene, 9,10-bis(2-ethyl Oxyethoxy)anthracene, 9,10-bis(2-butoxyethoxy)anthracene, 9,10-bis(3-butoxypropoxy)anthracene, 2-methyl- or 2- Ethyl-9,10-dimethoxyanthracene, 2-methyl- or 2-ethyl-9,10-diethoxyanthracene, 2-methyl- or 2-ethyl-9,10-di Propoxyanthracene, 2-methyl- or 2-ethyl-9,10-diisopropoxyanthracene, 2-methyl- or 2-ethyl-9,10-dibutoxyanthracene, 2- Methyl- or 2-ethyl-9,10-dipentyloxyanthracene, 2-methyl- or 2-ethyl-9,10-dihexyloxyanthracene, etc.
萘系化合物可列舉例如下述式(8)表示者。 Examples of the naphthalene-based compound include those represented by the following formula (8).
此處,式(8)中,R53及R54各自獨立地表示碳原子數1~6之烷基。 Here, in formula (8), R 53 and R 54 each independently represent an alkyl group having 1 to 6 carbon atoms.
列舉上述式(8)表示之萘系化合物之具體例時,有如以下的化合物。 When specific examples of the naphthalene-based compound represented by the above formula (8) are given, there are the following compounds.
可列舉例如4-甲氧基-1-萘酚、4-乙氧基-1-萘酚、4-丙氧基-1-萘酚、4-丁氧基-1-萘酚、4-己氧基-1-萘酚、1,4-二甲氧基萘、1-乙氧基-4-甲氧基萘、1,4-二乙氧基萘、1,4-二丙氧基萘、1,4-二丁氧基萘等。 Examples include 4-methoxy-1-naphthol, 4-ethoxy-1-naphthol, 4-propoxy-1-naphthol, 4-butoxy-1-naphthol, 4-hexyl Oxy-1-naphthol, 1,4-dimethoxynaphthalene, 1-ethoxy-4-methoxynaphthalene, 1,4-diethoxynaphthalene, 1,4-dipropoxynaphthalene , 1,4-Dibutoxynaphthalene, etc.
相對於上述陽離子聚合性成分(A)而言,增 感劑及增感助劑之使用比例無特別限定,只要在不阻礙本發明之目的的範圍內,大致以通常使用比例使用即可,例如相對於上述陽離子聚合性成分(A)100質量份,由提高硬化性的觀點,增感劑及增感助劑各自為0.1~3質量份為佳。 Compared with the above-mentioned cationically polymerizable component (A), it increases The use ratio of the sensitizer and the sensitization aid is not particularly limited, as long as it is within a range that does not hinder the purpose of the present invention, it may be used in a general use ratio, for example, relative to 100 parts by mass of the above-mentioned cationically polymerizable component (A), From the viewpoint of improving the curability, it is preferable that the sensitizer and the sensitization aid are each 0.1 to 3 parts by mass.
本發明之硬化性組成物中,可依需要使用矽烷偶合劑。矽烷偶合劑可使用例如二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、甲基乙基二甲氧基矽烷、甲基乙基二乙氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三甲氧基矽烷、乙基三甲氧基矽烷等之烷基官能性烷氧基矽烷、乙烯基三氯矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、烯丙基三甲氧基矽烷等之烯基官能性烷氧基矽烷、3-甲基丙烯醯氧基丙基三乙氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷、3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷、2-甲基丙烯醯氧基丙基三甲氧基矽烷、γ-環氧丙氧基丙基三甲氧基矽烷、γ-環氧丙氧基丙基甲基二乙氧基矽烷、β-(3,4-環氧基環己基)乙基三甲氧基矽烷等之環氧基官能性烷氧基矽烷、N-β(胺基乙基)-γ-胺基丙基三甲氧基矽烷、γ-胺基丙基三乙氧基矽烷、N-苯基-γ-胺基丙基三甲氧基矽烷等之胺基官能性烷氧基矽烷、γ-巰基丙基三甲氧基矽烷等之巰基官能性烷氧基矽烷、四異丙烷氧化鈦、四正丁烷氧化鈦等之烷氧化鈦類、鈦二辛氧基雙(伸辛基甘醇酸鹽)、鈦二異丙氧基雙(乙基乙醯乙酸鹽)等 之鈦鉗合物類、四乙醯丙酮鋯、三丁氧基單乙醯丙酮鋯等之鋯鉗合物類、三丁氧基硬脂酸鋯等之鋯醯化物類、甲基三異氰酸酯矽烷等之異氰酸酯矽烷類等。 In the curable composition of the present invention, a silane coupling agent can be used as needed. As the silane coupling agent, for example, dimethyldimethoxysilane, dimethyldiethoxysilane, methylethyldimethoxysilane, methylethyldiethoxysilane, and methyltrimethoxysilane can be used. , Methyl triethoxy silane, ethyl trimethoxy silane, ethyl trimethoxy silane and other alkyl functional alkoxy silanes, vinyl trichlorosilane, vinyl trimethoxy silane, vinyl triethyl Alkenyl functional alkoxysilanes such as oxysilane, allyltrimethoxysilane, etc., 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane Methoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 2-methacryloxypropyltrimethyl Oxyoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyl diethoxysilane, β-(3,4-epoxycyclohexyl)ethyl Epoxy functional alkoxysilane such as trimethoxysilane, N-β(aminoethyl)-γ-aminopropyl trimethoxysilane, γ-aminopropyltriethoxysilane, N -Phenyl-γ-aminopropyltrimethoxysilane such as amino functional alkoxysilane, γ-mercaptopropyltrimethoxysilane such as mercapto functional alkoxysilane, tetraisopropane titanium oxide, Titanium alkoxides such as tetra-n-butane titanium oxide, titanium dioctyloxy bis (octyl glycolate), titanium diisopropoxy bis (ethyl acetyl acetate), etc. Zirconium compounds such as titanium clamp compounds, zirconium tetraacetone acetone, zirconium tributoxy monoacetone zirconium acetonate, zirconium compounds such as zirconium tributoxy stearate, methyl triisocyanate silane And other isocyanate silanes, etc.
上述矽烷偶合劑之使用量並無特別限定,通常,相對於硬化性組成物中之固形物全部量100質量份,為0.01~20質量份的範圍。 The amount of the silane coupling agent used is not particularly limited, but it is usually in the range of 0.01 to 20 parts by mass relative to 100 parts by mass of the total solid content in the curable composition.
於本發明之硬化性組成物,依需要藉由使用熱可塑性有機聚合物,亦可改善硬化物之特性。熱可塑性有機聚合物,可列舉例如聚苯乙烯、聚甲基丙烯酸甲酯、甲基丙烯酸甲酯丙烯酸乙酯共聚物、甲基丙烯酸甲酯甲基丙烯酸縮水甘油酯共聚物、聚(甲基)丙烯酸、苯乙烯-(甲基)丙烯酸共聚物、(甲基)丙烯酸-甲基丙烯酸甲酯共聚物、(甲基)丙烯酸縮水甘油酯-聚甲基(甲基)丙烯酸酯共聚物、聚乙烯基縮丁醛、纖維素酯、聚丙烯醯胺、飽和聚酯等。 In the curable composition of the present invention, by using a thermoplastic organic polymer as needed, the properties of the cured product can also be improved. Thermoplastic organic polymers, for example, polystyrene, polymethyl methacrylate, methyl methacrylate ethyl acrylate copolymer, methyl methacrylate glycidyl methacrylate copolymer, poly(methyl) Acrylic acid, styrene-(meth)acrylic acid copolymer, (meth)acrylic acid-methyl methacrylate copolymer, glycidyl (meth)acrylate-polymethyl(meth)acrylate copolymer, polyethylene Butyral, cellulose ester, polyacrylamide, saturated polyester, etc.
本發明之硬化性組成物中,亦可依需要進一步使用紫外線吸收劑、或於常溫為不活性,且因加熱至特定溫度/光照射/酸等會使保護基脫離而活性化,展現紫外線吸收能力的化合物。 In the curable composition of the present invention, a UV absorber may be further used as needed, or it may be inactive at room temperature, and the protective group will be detached and activated by heating to a specific temperature/light irradiation/acid, etc., thereby exhibiting UV absorption Ability compound.
又,只要不損及本發明之效果時,可依需要添加多元醇、無機填料、有機填料、顏料、染料等之著色劑、消泡劑、增黏劑、界面活性劑、平坦劑、難燃劑、觸變劑、稀釋劑、可塑劑、安定劑、聚合抑制劑、紫外線吸收劑、抗氧化劑、抗靜電劑、流動調整劑、接著促進劑等 之各種樹脂添加物等。 In addition, as long as the effects of the present invention are not impaired, coloring agents such as polyols, inorganic fillers, organic fillers, pigments, dyes, defoamers, thickeners, surfactants, leveling agents, and flame retardants can be added as needed. Agents, thixotropic agents, diluents, plasticizers, stabilizers, polymerization inhibitors, ultraviolet absorbers, antioxidants, antistatic agents, flow regulators, adhesion promoters, etc. The various resin additives, etc.
本發明之硬化性組成物中,無特別限定,可使用通常所用之可溶解或分散上述(A)、(B)、(C)、(D)及(E)之各成分的溶劑。溶劑可列舉例如甲基乙基酮、甲基戊基酮、二乙基酮、丙酮、甲基異丙基酮、甲基異丁基酮、環己酮、2-庚酮等之酮類;乙醚、二噁烷、四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、丙二醇單甲醚、二丙二醇二甲醚等之醚系溶劑;乙酸甲酯、乙酸乙酯、乙酸-n-丙酯、乙酸異丙酯、乙酸n-丁酯、乙酸環己酯、乳酸乙酯、琥珀酸二甲酯、2,2,4-三甲基-1,3-戊二醇異丁酸(Texanol)等之酯系溶劑;乙二醇單甲醚、乙二醇單乙醚等之溶纖劑系溶劑;甲醇、乙醇、異-或n-丙醇、異-或n-丁醇、戊醇等之醇系溶劑;乙二醇單甲基乙酸酯、乙二醇單乙基乙酸酯、丙二醇-1-單甲醚-2-乙酸酯(PGMEA)、二丙二醇單甲醚乙酸酯、乙酸3-甲氧基丁酯、丙酸乙氧基乙酯等之醚酯系溶劑;苯、甲苯、二甲苯等之BTX系溶劑;己烷、庚烷、辛烷、環己烷等之脂肪族烴系溶劑;松節油、D-檸檬烯、蒎烯等之萜烯系烴油;礦油精、Swasol#310(Cosmo松山石油(股)公司製)、Solvesso#100(Exxon化學公司)等之鏈烷烴系溶劑;四氯化碳、氯仿、三氯乙烯、二氯甲烷、1,2-二氯乙烷等之鹵化脂肪族烴系溶劑;氯苯等之鹵化芳香族烴系溶劑;碳酸丙烯酯、卡必醇系溶劑、苯胺、三乙胺、吡啶、乙酸、乙腈、二硫化碳、N,N-二甲基甲醯胺、N,N-二甲基 乙醯胺、N-甲基吡咯烷酮、二甲基亞碸、水等。此等溶劑可使用1種或以2種以上之混合溶劑使用。 The curable composition of the present invention is not particularly limited, and commonly used solvents that can dissolve or disperse the above-mentioned (A), (B), (C), (D), and (E) components can be used. Examples of the solvent include ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, and 2-heptanone; Ether solvents such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, propylene glycol monomethyl ether, dipropylene glycol dimethyl ether, etc.; methyl acetate, Ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, 2,2,4-trimethyl-1,3 -Ester solvents such as pentanediol isobutyric acid (Texanol); cellosolve solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; methanol, ethanol, iso- or n-propanol, iso- Or alcohol solvents such as n-butanol and pentanol; ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2-acetate (PGMEA) , Dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, ethoxyethyl propionate and other ether ester solvents; benzene, toluene, xylene, etc. BTX solvents; hexane, heptane Aliphatic hydrocarbon solvents such as, octane and cyclohexane; terpene hydrocarbon oils such as turpentine, D-limonene, and pinene; mineral spirits, Swasol#310 (manufactured by Cosmo Matsuyama Petroleum Co., Ltd.), Solvesso #100 (Exxon Chemical Company) and other paraffinic solvents; halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, 1,2-dichloroethane, etc.; chlorobenzene, etc. Halogenated aromatic hydrocarbon solvents; propylene carbonate, carbitol-based solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N,N-dimethylformamide, N,N-dimethyl Acetamide, N-methylpyrrolidone, dimethyl sulfide, water, etc. These solvents can be used singly or as a mixture of two or more solvents.
本發明之硬化性組成物會提高硬化性、接著性、液體保存安定性,故水分量為5質量份以下較佳,又更佳為3質量份以下。水分過多時,有產生白濁或成分析出之疑慮,故不佳。 The curable composition of the present invention improves curability, adhesiveness, and liquid storage stability, so the water content is preferably 5 parts by mass or less, and more preferably 3 parts by mass or less. When there is too much water, it will cause white turbidity or doubts about the composition, so it is not good.
本發明之硬化性組成物以輥塗佈器、淋幕塗佈器、各種之印刷、浸漬等之公知手段適用於支撐基體上。又,可一旦施於薄膜等之支撐基體上後,轉印於其他支撐基體上,其適用方法並無限制。 The curable composition of the present invention is applied to the supporting substrate by known means such as roll coater, curtain coater, various printing, dipping, and the like. In addition, once applied to a supporting substrate such as a film, it can be transferred to other supporting substrates, and the application method is not limited.
上述支撐基體之材料,無特別限制,可使用通常所使用者,可列舉例如玻璃等之無機材料;二乙醯基纖維素、三乙醯基纖維素(TAC)、丙醯基纖維素、丁醯基纖維素、乙醯基丙醯基纖維素、硝基纖維素等之纖維素酯;聚醯胺;聚醯亞胺;聚胺基甲酸酯;環氧樹脂;聚碳酸酯;聚對苯二甲酸乙二酯、聚萘二甲酸乙二酯、聚對苯二甲酸丁二酯、聚-1,4-環己烷二亞甲基聚對苯二甲酸酯、聚乙烯-1,2-二苯氧基乙烷-4,4’-二羧酸酯、聚對苯二甲酸丁二酯等之聚酯;聚苯乙烯;聚乙烯、聚丙烯、聚甲基戊烯等之聚烯烴;聚乙酸乙烯酯、聚氯乙烯、聚氟乙烯等之乙烯基化合物;聚甲基丙烯酸甲酯、聚丙烯酸酯等之丙烯酸系樹脂;聚碳酸酯;聚碸;聚醚碸;聚醚酮;聚醚醯亞胺;聚氧乙烯、降莰烯樹脂、環烯烴聚合物(COP)等之高分子材料。又,亦可對上述支撐基體進行電暈放電處 理、火焰處理、紫外線處理、高頻處理、輝光放電處理、活性電漿處理、雷射處理等之表面活性化處理。 The material of the above-mentioned support matrix is not particularly limited, and ordinary users can be used, such as inorganic materials such as glass; diacetyl cellulose, triacetyl cellulose (TAC), acrylic cellulose, butyric cellulose Cellulose esters of cellulose, acetyl propyl cellulose, nitrocellulose, etc.; polyamide; polyimide; polyurethane; epoxy resin; polycarbonate; polyterephthalate Ethylene formate, polyethylene naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene polyterephthalate, polyethylene-1,2- Polyesters such as diphenoxyethane-4,4'-dicarboxylate and polybutylene terephthalate; polystyrene; polyolefins such as polyethylene, polypropylene, and polymethylpentene; Vinyl compounds such as polyvinyl acetate, polyvinyl chloride, and polyvinyl fluoride; acrylic resins such as polymethyl methacrylate and polyacrylate; polycarbonate; polyether; polyether ketone; polyether ketone; poly Ether imine; polyoxyethylene, norbornene resin, cyclic olefin polymer (COP) and other polymer materials. In addition, it is also possible to perform corona discharge on the above supporting substrate Surface activation treatments such as treatment, flame treatment, ultraviolet treatment, high frequency treatment, glow discharge treatment, active plasma treatment, laser treatment, etc.
藉由能量線照射本發明之硬化性組成物使硬化的方法中,能量線可列舉紫外線、電子線、X射線、放射線、高頻等,紫外線在經濟上最佳。紫外線之光源,可列舉紫外線雷射、水銀燈、氙雷射、金屬鹵素燈等。 In the method of curing by irradiating the curable composition of the present invention with energy rays, the energy rays include ultraviolet rays, electron rays, X-rays, radiation rays, high frequency, etc., and ultraviolet rays are economically optimal. The light source of ultraviolet light can include ultraviolet laser, mercury lamp, xenon laser, metal halide lamp, etc.
將本發明之硬化性組成物藉由加熱而硬化的方法的條件為70~250℃、1~100分鐘。可於預烤(PAB;Pre applied bake)之後加壓進行後烘烤(PEB;Post exposure bake);亦可以不同的數階段的溫度烘烤。加熱條件雖依各成分之種類及摻合比例而異,但例如70~180℃下,烘箱為5~15分鐘,加熱板則為1~5分鐘。然後,為了使塗膜硬化,藉由於180~250℃,較佳為200~250℃,於烘箱為30~90分鐘,加熱板則為5~30分鐘進行加熱處理,可得到硬化膜。 The conditions of the method of curing the curable composition of the present invention by heating are 70 to 250° C. for 1 to 100 minutes. It can be pressurized after pre-bake (PAB; Pre applied bake) to perform post-bake (PEB; Post exposure bake); it can also be baked at different temperatures in several stages. Although the heating conditions vary depending on the types and blending ratios of the ingredients, for example, at 70~180℃, the oven is 5~15 minutes, and the heating plate is 1~5 minutes. Then, in order to harden the coating film, heat treatment is performed at 180 to 250°C, preferably 200 to 250°C, in an oven for 30 to 90 minutes, and a hot plate for 5 to 30 minutes to obtain a cured film.
本發明之硬化性組成物或其硬化物之具體的用途,可列舉接著劑、眼鏡、以攝影用透鏡為代表之光學材料、塗料、塗覆劑、襯墊(lining)劑、油墨、阻劑、液狀阻劑、印刷版、彩色電視、PC監視器、行動資訊終端、數位相機、有機EL、觸控面板等之顯示元件、絕緣清漆、絕緣薄片、層合板、印刷基板、半導體裝置用/LED封裝用/液晶注入口用/有機EL用/光元件用/電絕緣用/電子零件用/分離膜用等之封裝劑、成形材料、油灰、玻璃纖維含浸劑、木粉填料、半導體用/太陽電池用等之鈍化膜、 層間絕緣膜、保護膜、液晶顯示裝置之背光所使用之稜鏡透鏡薄片、投影電視等之螢幕所使用之菲涅耳透鏡薄片、雙凸透鏡薄片等之透鏡薄片之透鏡部、或使用這種薄片之背光等、微透鏡等之光學透鏡、光學元件、光連接器、光波導、光學造形用鑄型劑等。 Specific uses of the curable composition of the present invention or its cured product include adhesives, glasses, optical materials represented by photographic lenses, paints, coating agents, lining agents, inks, and resists. , Liquid resists, printing plates, color TVs, PC monitors, mobile information terminals, digital cameras, organic EL, touch panels and other display elements, insulating varnishes, insulating sheets, laminates, printed circuit boards, semiconductor devices/ LED encapsulation/liquid crystal injection port/organic EL/optical element/electrical insulation/electronic parts/separation film, etc. encapsulant, molding material, putty, glass fiber impregnant, wood powder filler, semiconductor use/ Passivation film for solar cells, etc. Interlayer insulating films, protective films, lenticular lens sheets used in the backlight of liquid crystal display devices, Fresnel lens sheets used in screens such as projection TVs, lens parts of lens sheets such as lenticular lens sheets, or use of such sheets The backlight, etc., microlens, etc., optical lenses, optical components, optical connectors, optical waveguides, optical molding agents, etc.
顯示裝置可列舉於透明支撐體上依需要設置有底塗層、抗反射層、偏光元件層、相位差層、雙折射率層、光散射層、硬質塗層、潤滑層、保護層等之各層者,於各層可使用由本發明之硬化物所成的薄膜。 The display device can be enumerated on a transparent support provided with a primer layer, an anti-reflection layer, a polarizing element layer, a phase difference layer, a birefringence layer, a light scattering layer, a hard coating layer, a lubricating layer, a protective layer, etc., as required. Alternatively, a film made of the cured product of the present invention can be used for each layer.
以下列舉實施例等更詳細說明本發明,但本發明不限定於此等實施例。 Hereinafter, the present invention will be explained in more detail with examples and the like, but the present invention is not limited to these examples.
以下述[表1]~[表3]所示之調配,將各成分充分地混合,得到各實施例1~15之硬化性組成物及比較例1~3之硬化性組成物。又,實施例及比較例之單位為質量份。 With the formulations shown in the following [Table 1] to [Table 3], each component was sufficiently mixed to obtain the curable composition of each of Examples 1 to 15 and the curable composition of Comparative Examples 1 to 3. In addition, the units of Examples and Comparative Examples are parts by mass.
陽離子聚合性成分(A)係使用下述化合物(A1-1)~(A1-3)、(A2-1)~(A3-1)。 The following compounds (A1-1) to (A1-3) and (A2-1) to (A3-1) are used for the cationically polymerizable component (A).
化合物(A1-1):ADEKA RESINEP-4088L((股)ADEKA公司製) Compound (A1-1): ADEKA RESINEP-4088L (manufactured by ADEKA Corporation)
化合物(A1-2):1,6-己二醇二環氧丙醚 Compound (A1-2): 1,6-hexanediol diglycidyl ether
化合物(A1-3):新戊二醇二環氧丙醚 Compound (A1-3): neopentyl glycol diglycidyl ether
化合物(A2-1):ARON OXETANE OXT-221(東亞合成(股)公司製) Compound (A2-1): ARON OXETANE OXT-221 (manufactured by Toagosei Co., Ltd.)
化合物(A3-1):CELLOXID2021P(脂環式環氧基:(股)DAICEL公司製) Compound (A3-1): CELLOXID2021P (alicyclic epoxy group: manufactured by DAICEL Corporation)
陽離子聚合起始劑(B)使用下述化合物(B-1)。 As the cationic polymerization initiator (B), the following compound (B-1) was used.
化合物B-1:下述式(9)表示之化合物及下述式(10)表示之化合物之混合物的碳酸丙烯酯50%溶液 Compound B-1: Propylene carbonate 50% solution of a mixture of the compound represented by the following formula (9) and the compound represented by the following formula (10)
自由基聚合性成分(C)使用下述化合物(C2-1)~(C2-4)。 The following compounds (C2-1) to (C2-4) are used for the radically polymerizable component (C).
化合物(C2-1):1,6-己二醇二丙烯酸酯 Compound (C2-1): 1,6-hexanediol diacrylate
化合物(C2-2):三環癸烷二甲醇二丙烯酸酯 Compound (C2-2): Tricyclodecane dimethanol diacrylate
化合物(C2-3):乙氧基化異三聚氰酸三丙烯酸酯 Compound (C2-3): Ethoxylated isocyanuric acid triacrylate
化合物(C2-4):四氫糠基丙烯酸酯 Compound (C2-4): Tetrahydrofurfuryl acrylate
自由基聚合起始劑(D)使用下述化合物(D-1)。 The following compound (D-1) was used as the radical polymerization initiator (D).
化合物(D-1):IRGACURE184(BASF公司製) Compound (D-1): IRGACURE184 (manufactured by BASF Corporation)
聚合物(E)使用下述化合物(E-1)及(E-2)。 For the polymer (E), the following compounds (E-1) and (E-2) were used.
化合物(E-1):甲基甲基丙烯酸酯75質量份與環氧丙基甲基丙烯酸酯25質量份之共聚物(重量平均分子量7,000) Compound (E-1): a copolymer of 75 parts by mass of methacrylate and 25 parts by mass of glycidyl methacrylate (weight average molecular weight 7,000)
化合物(E-2):甲基甲基丙烯酸酯35質量份、苯乙烯35質量份及環氧丙基甲基丙烯酸酯30質量份之共聚物(重量平均分子量8,000) Compound (E-2): a copolymer of 35 parts by mass of methacrylate, 35 parts by mass of styrene, and 30 parts by mass of glycidyl methacrylate (weight average molecular weight 8,000)
關於所得之實施例1~15及比較例1~3之各硬化性組成物,依據下述步驟,評價玻璃轉移溫度(Tg)、彈性模數及密著性。結果一併記載於[表1]~[表3]。 Regarding the obtained curable compositions of Examples 1 to 15 and Comparative Examples 1 to 3, the glass transition temperature (Tg), elastic modulus, and adhesion were evaluated according to the following procedures. The results are recorded in [Table 1] ~ [Table 3].
將所得之實施例1~15及比較例1~3之各硬化性組成物分別以塗佈棒塗佈於聚對苯二甲酸乙二酯(PET)薄膜上形成30μm的厚度,使用金屬鹵素燈照射3000mJ/cm2之能量。24小時後,自薄膜取出接著劑硬化物,使用(股)Hitachi High-Tech Science製之黏彈性測量裝置(DMA7100),測量Tg及80℃下之彈性模數。 The obtained curable compositions of Examples 1 to 15 and Comparative Examples 1 to 3 were coated on a polyethylene terephthalate (PET) film with a coating bar to form a thickness of 30 μm, and a metal halide lamp was used. Irradiate the energy of 3000mJ/cm 2. After 24 hours, the cured adhesive was taken out from the film, and a viscoelasticity measuring device (DMA7100) manufactured by Hitachi High-Tech Science was used to measure Tg and elastic modulus at 80°C.
將上述所得之實施例之組成物1~15與比較例之組成物1~3,各自塗佈於一片電暈處理PMMA薄膜(住友化學(股)公司製:Technolloy 125S001)後,使用層合機與另一片經電暈放電處理的COP(環烯烴聚合物、日本Zeon(股)公司製:型號Zeonor Film 14-060)薄膜貼合,使用無電極紫外光燈透過COP薄膜照射相當於1000mJ/cm2之光進行接著,以得到試驗片。對於所得之試驗片進行90度剝離試驗。 The above-obtained composition 1 to 15 of the example and the composition 1 to 3 of the comparative example were each coated on a corona treated PMMA film (manufactured by Sumitomo Chemical Co., Ltd.: Technolloy 125S001), and then a laminator was used Laminated with another COP (cycloolefin polymer, manufactured by Japan Zeon Co., Ltd.: model Zeonor Film 14-060) film treated by corona discharge, and irradiated with an electrodeless ultraviolet lamp through the COP film equivalent to 1000mJ/cm The light of 2 is followed to obtain a test piece. A 90-degree peel test was performed on the obtained test piece.
由[表1]~[表3],得知本發明之硬化性組成物係硬化物之玻璃轉移溫度高,密著性優異。 From [Table 1] to [Table 3], it is known that the cured product of the curable composition system of the present invention has a high glass transition temperature and excellent adhesion.
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