TW201533080A - Light/moisture-curable resin composition, adhesive for electronic component, and adhesive for display device - Google Patents
Light/moisture-curable resin composition, adhesive for electronic component, and adhesive for display device Download PDFInfo
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- TW201533080A TW201533080A TW104101938A TW104101938A TW201533080A TW 201533080 A TW201533080 A TW 201533080A TW 104101938 A TW104101938 A TW 104101938A TW 104101938 A TW104101938 A TW 104101938A TW 201533080 A TW201533080 A TW 201533080A
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- Prior art keywords
- light
- moisture
- resin composition
- meth
- acrylate
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 97
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 25
- 239000000853 adhesive Substances 0.000 title claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 239000000945 filler Substances 0.000 claims abstract description 22
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims abstract description 7
- 238000013008 moisture curing Methods 0.000 claims description 30
- 239000003505 polymerization initiator Substances 0.000 claims description 13
- 239000011164 primary particle Substances 0.000 claims description 11
- 239000003605 opacifier Substances 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 abstract description 6
- 238000000576 coating method Methods 0.000 abstract description 6
- 230000014759 maintenance of location Effects 0.000 abstract description 6
- 239000007870 radical polymerization initiator Substances 0.000 abstract description 3
- -1 amine ester Chemical class 0.000 description 86
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 81
- 239000003822 epoxy resin Substances 0.000 description 36
- 229920000647 polyepoxide Polymers 0.000 description 36
- 229920005862 polyol Polymers 0.000 description 26
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 24
- 239000004593 Epoxy Substances 0.000 description 21
- 229920005989 resin Polymers 0.000 description 21
- 239000011347 resin Substances 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- 150000003254 radicals Chemical class 0.000 description 18
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- 239000000758 substrate Substances 0.000 description 15
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- 239000000126 substance Substances 0.000 description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 12
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- 238000006243 chemical reaction Methods 0.000 description 9
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
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- VZDDUFFXSBGRMP-UHFFFAOYSA-N 9h-fluoren-1-ylphosphane Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2P VZDDUFFXSBGRMP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
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- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 2
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- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
本發明係關於一種遮光性及接著性優異之光與濕氣硬化型樹脂組成物。又，本發明係關於一種使用該光與濕氣硬化型樹脂組成物而成之電子零件用接著劑及顯示元件用接著劑。 The present invention relates to a light and moisture-curable resin composition excellent in light-shielding properties and adhesion properties. Moreover, the present invention relates to an adhesive for an electronic component and an adhesive for a display element which are obtained by using the light and moisture-curable resin composition.
近年來，作為具有薄型、輕量、低消耗電力等特徵之顯示元件，業界廣泛地利用液晶顯示元件或有機EL顯示元件等。該等顯示元件中，通常於液晶或發光層之密封、基板或光學膜或保護膜或各種構件之接著等時使用光硬化型樹脂組成物。 In recent years, liquid crystal display elements, organic EL display elements, and the like have been widely used as display elements having characteristics such as thinness, light weight, and low power consumption. Among these display elements, a photocurable resin composition is usually used in the sealing of a liquid crystal or a light-emitting layer, a substrate, an optical film or a protective film, or a combination of various members.
且說，於行動電話、攜帶型遊戲機等附有各種顯示元件之移動機器正在普及之當代，顯示元件之小型化係最被要求之課題，作為小型化之方法，業界進行將圖像顯示部窄邊緣化之操作(以下，亦稱為窄邊緣設計)。然而，於窄邊緣設計中，存在於光未充分地到達之部分塗佈光硬化型樹脂組成物之情形，其結果有塗佈於光未到達之部分之光硬化型樹脂組成物的硬化變得不充分之問題。 In addition, in the modern era, mobile devices with various display elements, such as mobile phones and portable game machines, are becoming more and more popular. The miniaturization of display devices is the most demanding issue. As a method of miniaturization, the industry has narrowed the image display unit. Edged operation (hereinafter also referred to as narrow edge design). However, in the case of the narrow-edge design, the photocurable resin composition is applied to the portion where the light does not sufficiently reach, and as a result, the hardening of the photocurable resin composition applied to the portion where the light does not reach becomes hardened. Insufficient problem.
又，於將光硬化型樹脂組成物配置於光未充分地到達之部分之情形時，亦有如下問題：無法將自顯示元件之發光部透過光硬化型樹脂組成物 之光進行遮蔽，因漏光而降低對比度。 In addition, when the photocurable resin composition is disposed in a portion where light does not sufficiently reach, there is a problem in that the light-emitting portion from the display element cannot be transmitted through the photocurable resin composition. The light is shielded and the contrast is reduced due to light leakage.
因此，為了對光硬化型樹脂組成物賦予遮光性，考慮添加遮光劑之方法。然而，添加有遮光劑之光硬化型樹脂組成物有光硬化變得不充分之問題。於專利文獻1中，揭示有於在光硬化不充分之情形時亦可藉由加熱而使之充分地硬化之光與熱硬化型樹脂組成物中摻合遮光劑之方法，但有因高溫下之加熱而對元件等造成不良影響之虞。 Therefore, in order to provide a light-shielding property to the photocurable resin composition, a method of adding an opacifier is considered. However, the photocurable resin composition to which an opacifier is added has a problem that photocuring is insufficient. Patent Document 1 discloses a method of blending light and a heat-curable resin composition which are sufficiently hardened by heating in the case where the photocuring is insufficient, but at a high temperature. The heating causes damage to components and the like.
專利文獻1：日本特開2006-099027號公報 Patent Document 1: Japanese Laid-Open Patent Publication No. 2006-099027
本發明之目的在於提供一種遮光性及接著性優異之光與濕氣硬化型樹脂組成物。又，本發明之目的在於提供一種使用該光與濕氣硬化型樹脂組成物而成之電子零件用接著劑及顯示元件用接著劑。 An object of the present invention is to provide a light-and-moisture-curing resin composition which is excellent in light-shielding property and adhesion property. Moreover, an object of the present invention is to provide an adhesive for an electronic component and an adhesive for a display element which are obtained by using the light and moisture-curable resin composition.
本發明係含有自由基聚合性化合物、濕氣硬化型胺酯(urethane)樹脂、光自由基聚合起始劑、及遮光劑之光與濕氣硬化型樹脂組成物。 The present invention relates to a light-and-moisture-curing resin composition containing a radical polymerizable compound, a moisture-curing urethane resin, a photoradical polymerization initiator, and an opacifier.
以下對本發明進行詳細說明。 The invention is described in detail below.
本發明人等發現，作為不對含有遮光劑之樹脂組成物進行高溫下之加熱而使之硬化之方法，藉由在含有自由基聚合性化合物、濕氣硬 化型胺酯樹脂及光自由基聚合起始劑的光與濕氣硬化型樹脂組成物中摻合遮光劑，可獲得遮光性與接著性之兩者均優異之光與濕氣硬化型樹脂組成物，從而完成本發明。 The present inventors have found that a method of hardening a resin composition containing a light-shielding agent without heating at a high temperature is carried out by containing a radical polymerizable compound and moisture. A light-and-moisture-hardening resin composition is obtained by blending an opacifier with a light-moisture-curable resin composition of a modified amine ester resin and a photo-radical polymerization initiator to obtain an excellent light-shielding property and adhesion property. The invention thus completes the invention.
本發明之光與濕氣硬化型樹脂組成物含有遮光劑。藉由含有上述遮光劑，本發明之光與濕氣硬化型樹脂組成物成為遮光性優異者，而可防止顯示元件之漏光。 The light and moisture-curable resin composition of the present invention contains an opacifier. By including the above-mentioned light-shielding agent, the light-and-moisture-curable resin composition of the present invention is excellent in light-shielding property, and light leakage of the display element can be prevented.
再者，於本說明書中，上述「遮光劑」係指具有不易使可見光區域之光透過之能力之材料。 In the present specification, the term "sunscreen agent" means a material having an ability to easily transmit light in a visible light region.
作為上述遮光劑，例如可列舉：氧化鐵、鈦黑、苯胺黑、花青黑、富勒烯、碳黑、被覆樹脂型碳黑等。又，上述遮光劑可不為呈黑色者，只要為具有不易使可見光區域之光透過之能力之材料，則二氧化矽或滑石等下述列舉為填充劑之材料等亦可含有於上述遮光劑中。其中，較佳為鈦黑。 Examples of the light shielding agent include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and coated resin type carbon black. In addition, the light-shielding agent may not be black, and a material which is exemplified as a filler such as cerium oxide or talc may be contained in the light-shielding agent as long as it has a ability to transmit light in a visible light region. . Among them, titanium black is preferred.
關於上述鈦黑，係與針對波長300~800nm之光之平均透過率相比，對於紫外線區域附近、尤其是波長370~450nm之光之透過率增高之物質。即，上述鈦黑係藉由充分地遮蔽可見光區域之波長之光而對本發明之光與濕氣硬化型樹脂組成物賦予遮光性，另一方面，具有使紫外線區域附近之波長之光透過的性質之遮光劑。因此，藉由使用可利用使上述鈦黑之透過率增高之波長(370~450nm)之光而開始反應者作為光自由基聚合起始劑，從而可進一步增大本發明之光與濕氣硬化型樹脂組成物之光硬化性。又，另一方面，作為本發明之光與濕氣硬化型樹脂組成物中所含之遮光劑，較佳為絕緣性較高之物質，作為絕緣性較高之遮光劑，亦較佳為 鈦黑。 The titanium black is a substance having an increased transmittance in the vicinity of an ultraviolet region, particularly a light having a wavelength of 370 to 450 nm, as compared with an average transmittance of light having a wavelength of 300 to 800 nm. In other words, the titanium black imparts light shielding properties to the light and moisture-curable resin composition of the present invention by sufficiently shielding light of a wavelength in the visible light region, and has a property of transmitting light of a wavelength near the ultraviolet region. Sunscreen. Therefore, by using a light radical polymerization initiator which can start the reaction by using light having a wavelength (370 to 450 nm) in which the transmittance of the titanium black is increased, the light and moisture hardening of the present invention can be further increased. Photocurability of the resin composition. On the other hand, the light-shielding agent contained in the light-and-moisture-curing resin composition of the present invention is preferably a material having high insulating properties, and is preferably a light-shielding agent having high insulating properties. Titanium black.
上述鈦黑之光學密度(OD值)較佳為3以上，更佳為4以上。又，上述鈦黑之黑色度(L值)較佳為9以上，更佳為11以上。上述鈦黑之遮光性越高越佳，並不特別存在對上述鈦黑之OD值所較佳之上限，通常成為5以下。 The optical density (OD value) of the above titanium black is preferably 3 or more, more preferably 4 or more. Further, the blackness (L value) of the titanium black is preferably 9 or more, and more preferably 11 or more. The higher the light blocking property of the titanium black, the better, and the upper limit of the OD value of the titanium black is not particularly preferable, and is usually 5 or less.
關於上述鈦黑，即便為未經表面處理者，亦發揮出充分之效果，但亦可使用表面以偶合劑等有機成分進行處理者、或者利用氧化矽、氧化鈦、氧化鍺、氧化鋁、氧化鋯、氧化鎂等無機成分進行被覆者等經表面處理之鈦黑。其中，就可進一步提高絕緣性之觀點而言，較佳為利用有機成分進行處理者。 The titanium black described above exhibits sufficient effects even when it is not surface-treated, but it can also be treated with an organic component such as a coupling agent on the surface, or by using cerium oxide, titanium oxide, cerium oxide, aluminum oxide, or oxidation. An inorganic component such as zirconium or magnesium oxide is subjected to surface treatment of titanium black such as a coating. Among them, from the viewpoint of further improving the insulating property, it is preferred to carry out the treatment using an organic component.
又，關於使用本發明之光與濕氣硬化型樹脂組成物而製造之顯示元件，由於光與濕氣硬化型樹脂組成物具有充分之遮光性，故而無漏光，具有較高之對比度，而成為具有優異之圖像顯示品質者。 Further, the display element produced by using the light-and-moisture-curing resin composition of the present invention has sufficient light-shielding property as the light-moisture-curable resin composition, so that it has no light leakage and has a high contrast ratio. Excellent image display quality.
作為上述鈦黑中之市售者，例如可列舉：12S、13M、13M-C、13R-N(均為Mitsubishi Materials公司製造)、Tilack D(赤穗化成公司製造)等。 The commercially available ones of the titanium blacks include, for example, 12S, 13M, 13M-C, and 13R-N (all manufactured by Mitsubishi Materials Co., Ltd.) and Tilack D (manufactured by Ako Chemical Co., Ltd.).
上述鈦黑之比表面積之較佳之下限為5m2/g，較佳之上限為40m2/g，更佳之下限為10m2/g，更佳之上限為25m2/g。 A preferred lower limit of the specific surface area of the above titanium black is 5 m 2 /g, preferably an upper limit of 40 m 2 /g, a more preferred lower limit of 10 m 2 /g, and a more preferred upper limit of 25 m 2 /g.
又，關於上述鈦黑之薄片電阻之較佳之下限，於與樹脂混合之情形時(摻合70%)，為109Ω/□，更佳之下限為1011Ω/□。 Further, a preferred lower limit of the sheet resistance of the titanium black is 10 9 Ω/□ in the case of mixing with the resin (70% blending), and more preferably 10 11 Ω/□.
於本發明之光與濕氣硬化型樹脂組成物中，上述遮光劑之一次粒徑為顯示元件之基板間之距離以下等，可根據用途而進行適當選擇， 較佳之下限為30nm，較佳之上限為500nm。若上述遮光劑之一次粒徑未達30nm，則存在所獲得之光與濕氣硬化型樹脂組成物之黏度或搖變性會大幅增大，而作業性變差之情形。若上述遮光劑之一次粒徑超過500nm，則存在所獲得之光與濕氣硬化型樹脂組成物中之遮光劑之分散性降低，遮光性降低之情形。上述遮光劑之一次粒徑之更佳之下限為50nm，更佳之上限為200nm。 In the light-and-moisture-curing resin composition of the present invention, the primary particle diameter of the light-shielding agent is equal to or less than the distance between the substrates of the display element, and can be appropriately selected depending on the application. A preferred lower limit is 30 nm, and a preferred upper limit is 500 nm. When the primary particle diameter of the light-shielding agent is less than 30 nm, the viscosity and the shakenness of the obtained light-moisture-curable resin composition are greatly increased, and the workability is deteriorated. When the primary particle diameter of the light-shielding agent exceeds 500 nm, the dispersibility of the light-shielding agent in the obtained light and moisture-curable resin composition may be lowered, and the light-shielding property may be lowered. A more preferred lower limit of the primary particle diameter of the above-mentioned opacifier is 50 nm, and a more preferred upper limit is 200 nm.
本發明之光與濕氣硬化型樹脂組成物整體中之上述遮光劑之含量並無特別限定，較佳之下限為0.05重量%，較佳之上限為10重量%。若上述遮光劑之含量未達0.05重量%，則存在無法獲得充分之遮光性之情形。若上述遮光劑之含量超過10重量%，則存在所獲得之光與濕氣硬化型樹脂組成物之對基板等之接著性或硬化後之強度降低，或描繪性降低之情形。上述遮光劑之含量之更佳之下限為0.1重量%，更佳之上限為2重量%，進而更佳之下限為0.3重量%，進而較佳之上限為1重量%。 The content of the above-mentioned light shielding agent in the entire light and moisture-curable resin composition of the present invention is not particularly limited, and a preferred lower limit is 0.05% by weight, and a preferred upper limit is 10% by weight. If the content of the above-mentioned sunscreen agent is less than 0.05% by weight, sufficient light-shielding properties may not be obtained. When the content of the light-shielding agent is more than 10% by weight, the adhesion between the obtained light and the moisture-curable resin composition to the substrate or the like, or the strength after curing may be lowered, or the drawability may be lowered. A more preferred lower limit of the content of the above-mentioned sunscreen agent is 0.1% by weight, more preferably an upper limit of 2% by weight, still more preferably a lower limit of 0.3% by weight, and still more preferably an upper limit of 1% by weight.
本發明之光與濕氣硬化型樹脂組成物含有自由基聚合性化合物。 The light and moisture-curable resin composition of the present invention contains a radical polymerizable compound.
作為上述自由基聚合性化合物，只要為分子中具有自由基反應性官能基之化合物，則並無特別限定，較佳為具有不飽和雙鍵作為自由基反應性官能基之化合物，尤其是就反應性之方面而言，較佳為具有(甲基)丙烯醯基之樹脂(以下，亦稱為「(甲基)丙烯酸系樹脂」)。 The radical polymerizable compound is not particularly limited as long as it is a compound having a radical reactive functional group in the molecule, and is preferably a compound having an unsaturated double bond as a radical reactive functional group, especially in the reaction. In terms of properties, a resin having a (meth) acrylonitrile group (hereinafter also referred to as "(meth)acrylic resin") is preferred.
再者，於本說明書中，上述「(甲基)丙烯醯基」係指丙烯醯基或甲基丙烯醯基，上述「(甲基)丙烯酸」係指丙烯酸或甲基丙烯酸。 In the present specification, the above "(meth)acryl fluorenyl group" means an acryl fluorenyl group or a methacryl fluorenyl group, and the above "(meth)acrylic acid" means acrylic acid or methacrylic acid.
作為上述(甲基)丙烯酸系樹脂，例如可列舉：藉由使(甲 基)丙烯酸與具有羥基之化合物反應而獲得之酯化合物、藉由使(甲基)丙烯酸與環氧化合物反應而獲得之環氧(甲基)丙烯酸酯、藉由使異氰酸酯與具有羥基之(甲基)丙烯酸衍生物反應而獲得之(甲基)丙烯酸胺酯等。 As the (meth)acrylic resin, for example, An ester compound obtained by reacting acrylic acid with a compound having a hydroxyl group, an epoxy (meth)acrylate obtained by reacting (meth)acrylic acid with an epoxy compound, by reacting an isocyanate with a hydroxyl group The (meth)acrylic acid amine ester or the like obtained by the reaction of an acrylic acid derivative.
再者，於本說明書中，上述所謂「(甲基)丙烯酸酯」，係指丙烯酸酯或甲基丙烯酸酯。 In the present specification, the term "(meth)acrylate" as used herein means acrylate or methacrylate.
作為上述酯化合物中之單官能者，例如可列舉：N-丙烯醯氧基乙基六氫鄰苯二甲醯亞胺等鄰苯二甲醯亞胺丙烯酸酯類或各種醯亞胺丙烯酸酯、(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸4-羥基丁酯、(甲基)丙烯酸2-羥基丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸三級丁酯、(甲基)丙烯酸異辛酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸異莰酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸2-甲氧基乙酯、甲氧基乙二醇(甲基)丙烯酸酯、(甲基)丙烯酸2-乙氧基乙酯、(甲基)丙烯酸四氫糠酯、(甲基)丙烯酸苄酯、乙基卡必醇(甲基)丙烯酸酯、(甲基)丙烯酸苯氧基乙酯、苯氧基二乙二醇(甲基)丙烯酸酯、苯氧基聚乙二醇(甲基)丙烯酸酯、甲氧基聚乙二醇(甲基)丙烯酸酯、(甲基)丙烯酸2,2,2-三氟乙酯、(甲基)丙烯酸2,2,3,3-四氟丙酯、(甲基)丙烯酸1H,1H,5H-八氟戊酯、(甲基)丙烯酸醯亞胺酯、(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸異壬酯、(甲基)丙烯酸異肉豆蔻酯、(甲基)丙烯酸2-丁氧基乙酯、(甲基)丙烯酸2-苯氧基乙酯、(甲基)丙烯酸二環戊烯酯、(甲基) 丙烯酸異癸酯、(甲基)丙烯酸二乙基胺基乙酯、(甲基)丙烯酸二甲基胺基乙酯、琥珀酸2-(甲基)丙烯醯氧基乙酯、六氫鄰苯二甲酸2-(甲基)丙烯醯氧基乙酯、鄰苯二甲酸2-(甲基)丙烯醯氧基乙基-2-羥基丙酯、(甲基)丙烯酸環氧丙酯、磷酸2-(甲基)丙烯醯氧基乙酯等。 Examples of the monofunctional ones of the above ester compounds include phthalimide acrylates such as N-propylene methoxyethyl hexahydrophthalimide or various quinone acrylates. 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, (meth)acrylic acid Butyl ester, tert-butyl (meth)acrylate, isooctyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, isodecyl (meth)acrylate, (A) Base) cyclohexyl acrylate, 2-methoxyethyl (meth)acrylate, methoxyethylene glycol (meth) acrylate, 2-ethoxyethyl (meth) acrylate, (methyl) Tetrahydrofurfuryl acrylate, benzyl (meth) acrylate, ethyl carbitol (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxy diethylene glycol (meth) acrylate , phenoxy polyethylene glycol (meth) acrylate, methoxy polyethylene glycol (meth) acrylate, 2,2,2-trifluoroethyl (meth) acrylate, (meth) acrylate 2,2,3,3-tetrafluoropropyl ester, (meth)acrylic acid 1H,1H,5H-octafluoropentyl ester, benzylimine (meth)acrylate, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, (methyl) Propyl acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, isodecyl (meth)acrylate, isomyristyl (meth)acrylate, (meth)acrylic acid 2 -butoxyethyl ester, 2-phenoxyethyl (meth)acrylate, dicyclopentenyl (meth)acrylate, (methyl) Isodecyl acrylate, diethylaminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, 2-(methyl)propenyloxyethyl succinate, hexahydroortylene 2-(methyl)propenyloxyethyl dicarboxylate, 2-(methyl)propenyloxyethyl-2-hydroxypropyl phthalate, glycidyl (meth)acrylate, phosphoric acid 2 -(Meth)acryloxyethyl ester and the like.
又，作為上述酯化合物中之2官能者，例如可列舉：1,4-丁二醇二(甲基)丙烯酸酯、1,3-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、1,10-癸二醇二(甲基)丙烯酸酯、2-正丁基-2-乙基-1,3-丙二醇二(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、聚丙二醇(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、環氧丙烷加成雙酚A二(甲基)丙烯酸酯、環氧乙烷加成雙酚A二(甲基)丙烯酸酯、環氧乙烷加成雙酚F二(甲基)丙烯酸酯、二(甲基)丙烯酸二羥甲基二環戊二烯酯、新戊二醇二(甲基)丙烯酸酯、環氧乙烷改質異三聚氰酸二(甲基)丙烯酸酯、(甲基)丙烯酸2-羥基-3-(甲基)丙烯醯氧基丙酯、碳酸酯二醇二(甲基)丙烯酸酯、聚醚二醇二(甲基)丙烯酸酯、聚酯二醇二(甲基)丙烯酸酯、聚己內酯二醇二(甲基)丙烯酸酯、聚丁二烯二醇二(甲基)丙烯酸酯等。 Further, examples of the bifunctional ones of the above ester compounds include 1,4-butanediol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, and 1,6- Hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-nonanediol di(meth)acrylate, 2-n-butyl-2-ethyl -1,3-propanediol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol (meth)acrylate, ethylene glycol di(a) Acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene oxide addition bisphenol A (Meth) acrylate, ethylene oxide addition bisphenol A di(meth) acrylate, ethylene oxide addition bisphenol F di(meth) acrylate, di(meth) acrylate dihydroxyl Dicyclopentadienyl ester, neopentyl glycol di(meth)acrylate, ethylene oxide modified di(meth)acrylate isocyanate, 2-hydroxy-3-(meth)acrylate (Meth) propylene methoxy propyl ester, carbonate diol di(meth) acrylate, polyether diol (Meth) acrylate, polyester diol di (meth) acrylate, polycaprolactone glycol di (meth) acrylate, polybutadiene diol di (meth) acrylate.
又，作為上述酯化合物中之3官能以上者，例如可列舉：新戊四醇三(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、環氧丙烷加成三羥甲基丙烷三(甲基)丙烯酸酯、環氧乙烷加成三羥甲基丙烷三(甲基)丙烯酸酯、己內酯改質三羥甲基丙烷三(甲基)丙烯酸酯、環氧 乙烷加成異三聚氰酸三(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、二-三羥甲基丙烷四(甲基)丙烯酸酯、新戊四醇四(甲基)丙烯酸酯、三(甲基)丙烯酸甘油酯、環氧丙烷加成三(甲基)丙烯酸甘油酯、磷酸三(甲基)丙烯醯氧基乙酯等。 In addition, examples of the trifunctional or higher of the above ester compounds include pentaerythritol tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, and propylene oxide addition tris. Propane tri(meth)acrylate, ethylene oxide addition trimethylolpropane tri(meth)acrylate, caprolactone modified trimethylolpropane tri(meth)acrylate, epoxy Ethane addition of tris (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, di-trimethylolpropane Tetrakis (meth) acrylate, neopentyl alcohol tetra (meth) acrylate, tris (meth) acrylate, propylene oxide addition tris (meth) acrylate, tris (methyl) propylene phosphate Ethyloxyethyl ester and the like.
作為上述環氧(甲基)丙烯酸酯，例如可列舉藉由根據常法於鹼性觸媒之存在下使環氧化合物與(甲基)丙烯酸進行反應而獲得者等。 Examples of the epoxy (meth) acrylate include those obtained by reacting an epoxy compound with (meth)acrylic acid in the presence of a basic catalyst according to a usual method.
作為成為用於合成上述環氧(甲基)丙烯酸酯之原料之環氧化合物，例如可列舉：雙酚A型環氧樹脂、雙酚F型環氧樹脂、雙酚S型環氧樹脂、2,2'-二烯丙基雙酚A型環氧樹脂、氫化雙酚型環氧樹脂、環氧丙烷加成雙酚A型環氧樹脂、間苯二酚型環氧樹脂、聯苯型環氧樹脂、硫醚型環氧樹脂、二苯醚型環氧樹脂、二環戊二烯型環氧樹脂、萘型環氧樹脂、苯酚酚醛清漆型環氧樹脂、鄰甲酚酚醛清漆型環氧樹脂、二環戊二烯酚醛清漆型環氧樹脂、聯苯酚醛清漆型環氧樹脂、萘酚酚醛清漆型環氧樹脂、環氧丙胺型環氧樹脂、烷基多元醇型環氧樹脂、橡膠改質型環氧樹脂、環氧丙酯化合物、雙酚A型環硫樹脂等。 Examples of the epoxy compound to be used as a raw material for synthesizing the above epoxy (meth) acrylate include bisphenol A type epoxy resin, bisphenol F type epoxy resin, and bisphenol S type epoxy resin, and 2 , 2'-diallyl bisphenol A epoxy resin, hydrogenated bisphenol epoxy resin, propylene oxide addition bisphenol A epoxy resin, resorcinol epoxy resin, biphenyl ring Oxygen resin, thioether type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, phenol novolak type epoxy resin, o-cresol novolac type epoxy Resin, dicyclopentadiene novolac type epoxy resin, biphenyl novolac type epoxy resin, naphthol novolac type epoxy resin, epoxy propylamine type epoxy resin, alkyl polyol type epoxy resin, rubber Modified epoxy resin, glycidyl ester compound, bisphenol A type episulfide resin, and the like.
作為上述雙酚A型環氧樹脂中之市售者，例如可列舉：jER828EL、jER1001、jER1004(均為三菱化學公司製造)、Epicion 850-S(DIC公司製造)等。 The commercially available ones of the bisphenol A type epoxy resins include, for example, jER828EL, jER1001, jER1004 (all manufactured by Mitsubishi Chemical Corporation), and Epicion 850-S (manufactured by DIC Corporation).
作為上述雙酚F型環氧樹脂中之市售者，例如可列舉：jER806、jER4004(均為三菱化學公司製造)等。 The commercially available one of the bisphenol F-type epoxy resins may, for example, be jER806 or jER4004 (all manufactured by Mitsubishi Chemical Corporation).
作為上述雙酚S型環氧樹脂中之市售者，例如可列舉Epicion EXA1514(DIC公司製造)等。 As a commercial item of the said bisphenol S type epoxy resin, Epicion EXA1514 (made by the DIC company) etc. are mentioned, for example.
作為上述2,2'-二烯丙基雙酚A型環氧樹脂中之市售者，例如可列舉RE-810NM(日本化藥公司製造)等。 The commercially available one of the 2,2'-diallyl bisphenol A type epoxy resins is, for example, RE-810NM (manufactured by Nippon Kayaku Co., Ltd.).
作為上述氫化雙酚型環氧樹脂中之市售者，例如可列舉Epicion EXA7015(DIC公司製造)等。 The commercially available one of the hydrogenated bisphenol type epoxy resins is Epicion EXA 7015 (manufactured by DIC Corporation).
作為上述環氧丙烷加成雙酚A型環氧樹脂中之市售者，例如可列舉EP-4000S(ADEKA公司製造)等。 The commercially available one of the above-mentioned propylene oxide-added bisphenol A-type epoxy resins is, for example, EP-4000S (manufactured by Adeka Co., Ltd.).
作為上述間苯二酚型環氧樹脂中之市售者，例如可列舉EX-201(Nagase chemtex公司製造)等。 The commercially available one of the resorcinol-type epoxy resins is, for example, EX-201 (manufactured by Nagase Chemtex Co., Ltd.).
作為上述聯苯型環氧樹脂中之市售者，例如可列舉jERYX-4000H(三菱化學公司製造)等。 As a commercial item of the above-mentioned biphenyl type epoxy resin, jERYX-4000H (made by Mitsubishi Chemical Corporation), etc. are mentioned, for example.
作為上述硫醚型環氧樹脂中之市售者，例如可列舉YSLV-50TE(新日鐵住金化學公司製造)等。 For example, YSLV-50TE (manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.) or the like can be mentioned as a commercially available one of the above-mentioned thioether type epoxy resins.
作為上述二苯醚型環氧樹脂中之市售者，例如可列舉YSLV-80DE(新日鐵住金化學公司製造)等。 For example, YSLV-80DE (manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.) and the like can be cited as a commercially available one of the above-mentioned diphenyl ether type epoxy resins.
作為上述二環戊二烯型環氧樹脂中之市售者，例如可列舉EP-4088S(ADEKA公司製造)等。 The commercially available one of the above-mentioned dicyclopentadiene type epoxy resins is, for example, EP-4088S (manufactured by Adeka Co., Ltd.).
作為上述萘型環氧樹脂中之市售者，例如可列舉Epicion HP4032、Epicion EXA-4700(均為DIC公司製造)等。 As a commercial item of the above-mentioned naphthalene type epoxy resin, Epicion HP4032, Epicion EXA-4700 (all manufactured by DIC Corporation), etc. are mentioned, for example.
作為上述苯酚酚醛清漆型環氧樹脂中之市售者，例如可列舉Epicion N-770(DIC公司製造)等。 As a commercial item of the above-mentioned phenol novolak type epoxy resin, Epicion N-770 (made by DIC Corporation) etc. are mentioned, for example.
作為上述鄰甲酚酚醛清漆型環氧樹脂中之市售者，例如可列舉Epicion N-670-EXP-S(DIC公司製造)等。 As a commercial item of the above-mentioned o-cresol novolak type epoxy resin, Epicion N-670-EXP-S (made by DIC Corporation) etc. are mentioned, for example.
作為上述二環戊二烯酚醛清漆型環氧樹脂中之市售者，例如可列舉Epicion HP7200(DIC公司製造)等。 As a commercial item of the above-mentioned dicyclopentadiene novolac type epoxy resin, Epicion HP7200 (made by DIC Corporation) etc. are mentioned, for example.
作為上述聯苯酚醛清漆型環氧樹脂中之市售者，例如可列舉NC-3000P(日本化藥公司製造)等。 The commercially available one of the above-mentioned biphenyl novolak type epoxy resins is, for example, NC-3000P (manufactured by Nippon Kayaku Co., Ltd.).
作為上述萘酚酚醛清漆型環氧樹脂中之市售者，例如可列舉ESN-165S(新日鐵住金化學公司製造)等。 As a commercial item of the above-mentioned naphthol novolac type epoxy resin, ESN-165S (made by Nippon Steel & Sumitomo Chemical Co., Ltd.), etc. are mentioned, for example.
作為上述環氧丙胺型環氧樹脂中之市售者，例如可列舉：jER630(三菱化學公司製造)、Epicion 430(DIC公司製造)、TETRAD-X(三菱瓦斯化學公司製造)等。 For example, jER630 (manufactured by Mitsubishi Chemical Corporation), Epicion 430 (manufactured by DIC Corporation), TETRAD-X (manufactured by Mitsubishi Gas Chemical Co., Ltd.), and the like are mentioned as a commercially available one.
作為上述烷基多元醇型環氧樹脂中之市售者，例如可列舉：ZX-1542(新日鐵住金化學公司製造)、Epicion 726(DIC公司製造)、Epolight 80MFA(共榮社化學公司製造)、DENACOL EX-611(Nagase chemtex公司製造)等。 For example, ZX-1542 (manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.), Epicion 726 (manufactured by DIC Corporation), and Epolight 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.) are mentioned as a commercial product of the above-mentioned alkyl polyol type epoxy resin. ), DENACOL EX-611 (manufactured by Nagase Chemex), and the like.
作為上述橡膠改質型環氧樹脂中之市售者，例如可列舉：YR-450、YR-207(均為新日鐵住金化學公司製造)、Epolead PB(Daicel公司製造)等。 For example, YR-450, YR-207 (all manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.), Epolead PB (manufactured by Daicel Co., Ltd.), and the like are mentioned as a commercially available one of the rubber-modified epoxy resins.
作為上述環氧丙酯化合物中之市售者，例如可列舉DENACOL EX-147(Nagase chemtex公司製造)等。 The commercially available one of the above-mentioned glycidyl ester compounds is, for example, DENACOL EX-147 (manufactured by Nagase Chemtex Co., Ltd.).
作為上述雙酚A型環硫樹脂中之市售者，例如可列舉jERYL-7000(三菱化學公司製造)等。 For example, jERYL-7000 (manufactured by Mitsubishi Chemical Corporation) or the like can be mentioned as a commercially available product of the bisphenol A-type episulfide resin.
作為上述環氧樹脂中之其他市售者，例如可列舉：YDC-1312、YSLV-80XY、YSLV-90CR(均為新日鐵住金化學公司製造)、XAC4151(旭化成公司製造)、jER1031、jER1032(均為三菱化學公司製造)、EXA-7120(DIC 公司製造)、TEPIC(日產化學公司製造)等。 Other commercially available ones of the above-mentioned epoxy resins include, for example, YDC-1312, YSLV-80XY, YSLV-90CR (all manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.), XAC4151 (manufactured by Asahi Kasei Corporation), jER1031, and jER1032 ( All manufactured by Mitsubishi Chemical Corporation), EXA-7120 (DIC Made by the company), TEPIC (manufactured by Nissan Chemical Co., Ltd.), etc.
作為上述環氧(甲基)丙烯酸酯中之市售者，例如可列舉：EBECRYL860、EBECRYL3200、EBECRYL3201、EBECRYL3412、EBECRYL3600、EBECRYL3700、EBECRYL3701、EBECRYL3702、EBECRYL3703、EBECRYL3800、EBECRYL6040、EBECRYL RDX63182(均為Daicel allnex公司製造)、EA-1010、EA-1020、EA-5323、EA-5520、EA-CHD、EMA-1020(均為新中村化學工業公司製造)、Epoxy Ester M-600A、Epoxy Ester 40EM、Epoxy Ester 70PA、Epoxy Ester 200PA、Epoxy Ester 80MFA、Epoxy Ester 3002M、Epoxy Ester 3002A、Epoxy Ester 1600A、Epoxy Ester 3000M、Epoxy Ester 3000A、Epoxy Ester 200EA、Epoxy Ester 400EA(均為共榮社化學公司製造)、Denacol Acrylate DA-141、Denacol Acrylate DA-314、Denacol Acrylate DA-911(均為Nagase chemtex公司製造)等。 As a commercially available one of the above-mentioned epoxy (meth)acrylates, EBECRYL 860, EBECRYL 3200, EBECRYL 3201, EBECRYL 3102, EBECRYL 3600, EBECRYL 3700, EBECRYL 3701, EBECRYL 3702, EBECRYL 3703, EBECRYL 3800, EBECRYL 6040, EBECRYL RDX 63182 (all are Daicel allnex companies) Manufacturing), EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (all manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), Epoxy Ester M-600A, Epoxy Ester 40EM, Epoxy Ester 70PA , Epoxy Ester 200PA, Epoxy Ester 80MFA, Epoxy Ester 3002M, Epoxy Ester 3002A, Epoxy Ester 1600A, Epoxy Ester 3000M, Epoxy Ester 3000A, Epoxy Ester 200EA, Epoxy Ester 400EA (all manufactured by Kyoei Chemical Co., Ltd.), Denacol Acrylate DA -141, Denacol Acrylate DA-314, Denacol Acrylate DA-911 (all manufactured by Nagase Chemex), and the like.
關於上述(甲基)丙烯酸胺酯，例如可藉由相對於具有2個異氰酸酯基之化合物1當量，使具有羥基之(甲基)丙烯酸衍生物2當量於觸媒量之錫系化合物存在下進行反應而獲得。 The above-mentioned (meth)acrylic acid amide can be, for example, carried out in the presence of a tin-based compound having a hydroxyl group-containing (meth)acrylic acid derivative of 2 equivalents to a catalyst amount per equivalent of a compound having two isocyanate groups. Obtained by reaction.
作為成為上述(甲基)丙烯酸胺酯之原料之異氰酸酯，例如可列舉：異佛爾酮二異氰酸酯、2,4-甲苯二異氰酸酯、2,6-甲苯二異氰酸酯、六亞甲基二異氰酸酯、三甲基六亞甲基二異氰酸酯、二苯基甲烷-4,4'-二異氰酸酯(MDI)、氫化MDI、聚合MDI、1,5-萘二異氰酸酯、降莰烷二異氰酸酯、聯甲苯胺二異氰酸酯、苯二甲基二異氰酸酯(XDI)、氫化XDI、離胺酸二異氰酸酯、三苯基甲烷三異氰酸酯、三(異氰酸酯基苯基)硫代磷酸酯、四甲基二甲苯二異氰酸酯、1,6,11-十一烷三異氰酸酯等。 Examples of the isocyanate which is a raw material of the above (meth)acrylic acid amide include isophorone diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, hexamethylene diisocyanate, and the like. Methylhexamethylene diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate , benzodimethyl diisocyanate (XDI), hydrogenated XDI, diazonic acid diisocyanate, triphenylmethane triisocyanate, tris(isocyanate phenyl) phosphorothioate, tetramethyl xylene diisocyanate, 1,6 , 11-undecane triisocyanate, and the like.
又，作為上述異氰酸酯，例如亦可使用藉由乙二醇、甘油、山梨糖醇、三羥甲基丙烷、(聚)丙二醇、碳酸酯二醇、聚醚二醇、聚酯二醇、聚己內酯二醇等多元醇與過量異氰酸酯之反應而獲得之經鏈延長之異氰酸酯化合物。 Further, as the above isocyanate, for example, ethylene glycol, glycerin, sorbitol, trimethylolpropane, (poly)propylene glycol, carbonate diol, polyether diol, polyester diol, poly propylene can also be used. A chain extended isocyanate compound obtained by reacting a polyol such as a lactone diol with an excess of isocyanate.
作為成為上述(甲基)丙烯酸胺酯之原料之具有羥基之(甲基)丙烯酸衍生物，例如可列舉：乙二醇、1,2-丙二醇、1,3-丙二醇、1,3-丁二醇、1,4-丁二醇、聚乙二醇等二元醇之單(甲基)丙烯酸酯、或三羥甲基乙烷、三羥甲基丙烷、甘油等三元醇之單(甲基)丙烯酸酯或二(甲基)丙烯酸酯、或者雙酚A型環氧(甲基)丙烯酸酯等環氧(甲基)丙烯酸酯等。 Examples of the (meth)acrylic acid derivative having a hydroxyl group which is a raw material of the above (meth)acrylic acid amide include ethylene glycol, 1,2-propylene glycol, 1,3-propanediol, and 1,3-butylene. a mono (meth) acrylate of a glycol such as an alcohol, 1,4-butanediol or polyethylene glycol, or a monohydric alcohol such as trimethylolethane, trimethylolpropane or glycerol. Epoxy (meth) acrylate such as acrylate or di(meth) acrylate or bisphenol A epoxy (meth) acrylate.
作為上述(甲基)丙烯酸胺酯中之市售者，例如可列舉：M-1100、M-1200、M-1210、M-1600(均為東亞合成公司製造)、EBECRYL230、EBECRYL270、EBECRYL4858、EBECRYL8402、EBECRYL8411、EBECRYL8412、EBECRYL8413、EBECRYL8804、EBECRYL8803、EBECRYL8807、EBECRYL9260、EBECRYL1290、EBECRYL5129、EBECRYL4842、EBECRYL210、EBECRYL4827、EBECRYL6700、EBECRYL220、EBECRYL2220、KRM7735、KRM-8295(均為Daicel allnex公司製造)、Artresin UN-9000H、Artresin UN-9000A、Artresin UN-7100、Artresin UN-1255、Artresin UN-330、Artresin UN-3320HB、Artresin UN-1200TPK、Artresin SH-500B(均為根上工業公司製造)、U-2HA、U-2PHA、U-3HA、U-4HA、U-6H、U-6LPA、U-6HA、U-10H、U-15HA、U-122A、U-122P、U-108、U-108A、U-324A、U-340A、 U-340P、U-1084A、U-2061BA、UA-340P、UA-4100、UA-4000、UA-4200、UA-4400、UA-5201P、UA-7100、UA-7200、UA-W2A(均為新中村化學工業公司製造)、AI-600、AH-600、AT-600、UA-101I、UA-101T、UA-306H、UA-306I、UA-306T(均為共榮社化學公司製造)等。 For example, M-1100, M-1200, M-1210, M-1600 (all manufactured by Toagosei Co., Ltd.), EBECRYL230, EBECRYL270, EBECRYL4858, EBECRYL8402 are exemplified as the commercially available (meth) acrylate. , EBECRYL8411, EBECRYL8412, EBECRYL8413, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9260, EBECRYL1290, EBECRYL5129, EBECRYL4842, EBECRYL210, EBECRYL4827, EBECRYL6700, EBECRYL220, EBECRYL2220, KRM7735, KRM-8295 (all manufactured by Daicel allnex), Artresin UN-9000H, Artresin UN-9000A, Artresin UN-7100, Artresin UN-1255, Artresin UN-330, Artresin UN-3320HB, Artresin UN-1200TPK, Artresin SH-500B (all manufactured by Gensei Industrial Co., Ltd.), U-2HA, U-2PHA , U-3HA, U-4HA, U-6H, U-6LPA, U-6HA, U-10H, U-15HA, U-122A, U-122P, U-108, U-108A, U-324A, U -340A, U-340P, U-1084A, U-2061BA, UA-340P, UA-4100, UA-4000, UA-4200, UA-4400, UA-5201P, UA-7100, UA-7200, UA-W2A (all Manufactured by Shin-Nakamura Chemical Industry Co., Ltd., AI-600, AH-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T (all manufactured by Kyoeisha Chemical Co., Ltd.) .
又，亦可適當使用上述以外之其他自由基聚合性化合物。 Further, other radical polymerizable compounds other than the above may be suitably used.
作為上述其他自由基聚合性化合物，例如可列舉：N,N-二甲基(甲基)丙烯醯胺、N-(甲基)丙烯醯基嗎福啉、N-羥基乙基(甲基)丙烯醯胺、N,N-二乙基(甲基)丙烯醯胺、N-異丙基(甲基)丙烯醯胺、N,N-二甲基胺基丙基(甲基)丙烯醯胺等(甲基)丙烯醯胺化合物；苯乙烯、α-甲基苯乙烯、N-吡咯啶酮、N-乙烯基己內酯等乙烯系化合物等。 Examples of the other radically polymerizable compound include N,N-dimethyl(meth)acrylamide, N-(methyl)propenyl rufofen, and N-hydroxyethyl (methyl). Acrylamide, N,N-diethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, N,N-dimethylaminopropyl(meth)acrylamide A (meth) acrylamide compound; a vinyl compound such as styrene, α-methylstyrene, N-pyrrolidone or N-vinylcaprolactone.
關於上述自由基聚合性化合物，就調整硬化性等觀點而言，較佳為含有單官能自由基聚合性化合物與多官能自由基聚合性化合物。於僅使用單官能自由基聚合性化合物之情形時，存在所獲得之光與濕氣硬化型樹脂組成物成為硬化性較差者之情形，於僅使用多官能自由基聚合性化合物之情形時，存在所獲得之光與濕氣硬化型樹脂組成物成為黏性較差者之情形。其中，更佳為組合使用作為上述單官能自由基聚合性化合物之分子中具有氮原子之化合物、及作為上述多官能自由基聚合性化合物之(甲基)丙烯酸胺酯。又，上述多官能自由基聚合性化合物較佳為2官能或3官能，更佳為2官能。 The radical polymerizable compound preferably contains a monofunctional radical polymerizable compound and a polyfunctional radical polymerizable compound from the viewpoint of adjusting the curability and the like. In the case where only a monofunctional radically polymerizable compound is used, there is a case where the obtained light and the moisture-curable resin composition are inferior in curability, and when a polyfunctional radical polymerizable compound is used only, there is a case where it is used. The obtained light and moisture-curable resin composition are inferior in viscosity. In particular, a compound having a nitrogen atom in the molecule of the monofunctional radical polymerizable compound and an (meth)acrylic acid ester ester as the polyfunctional radical polymerizable compound are preferably used in combination. Further, the polyfunctional radically polymerizable compound is preferably a bifunctional or a trifunctional, more preferably a bifunctional.
於上述自由基聚合性化合物含有上述單官能自由基聚合性化合物與上述多官能自由基聚合性化合物之情形時，上述多官能自由基聚合性化合物之含量係相對於上述單官能自由基聚合性化合物與上述多官能 自由基聚合性化合物之合計100重量份，較佳之下限為2重量份，較佳之上限為30重量份。若上述多官能自由基聚合性化合物之含量未達2重量份，則存在所獲得之光與濕氣硬化型樹脂組成物成為硬化性較差者之情形。若上述多官能自由基聚合性化合物之含量超過30重量份，則存在所獲得之光與濕氣硬化型樹脂組成物成為黏性較差者之情形。上述多官能自由基聚合性化合物之含量之更佳之下限為5重量份，更佳之上限為20重量份。 In the case where the radically polymerizable compound contains the monofunctional radically polymerizable compound and the polyfunctional radically polymerizable compound, the content of the polyfunctional radically polymerizable compound is relative to the monofunctional radically polymerizable compound. Multifunctional with the above The total amount of the radically polymerizable compound is 100 parts by weight, preferably the lower limit is 2 parts by weight, and the upper limit is preferably 30 parts by weight. When the content of the polyfunctional radically polymerizable compound is less than 2 parts by weight, the obtained light and the moisture-curable resin composition may be inferior in curability. When the content of the polyfunctional radically polymerizable compound exceeds 30 parts by weight, the obtained light and the moisture-curable resin composition may be inferior in viscosity. A more preferred lower limit of the content of the above polyfunctional radically polymerizable compound is 5 parts by weight, and a more preferred upper limit is 20 parts by weight.
本發明之光與濕氣硬化型樹脂組成物含有濕氣硬化型胺酯樹脂。 The light and moisture-curable resin composition of the present invention contains a moisture-curable amine ester resin.
上述濕氣硬化型胺酯樹脂中，分子內之異氰酸酯基與空氣中或被接著體中之水分進行反應而發生硬化。又，與使用具有交聯性矽基之化合物等作為濕氣硬化成分之情形相比，所獲得之光與濕氣硬化型樹脂組成物成為速硬化性優異者。 In the moisture-curable amine ester resin, the isocyanate group in the molecule is hardened by reacting with water or by moisture in the adherend. In addition, the obtained light and the moisture-curable resin composition are excellent in quick-curing property as compared with the case of using a compound having a crosslinkable sulfhydryl group as a moisture-curing component.
上述濕氣硬化型胺酯樹脂於1分子中可僅具有1個異氰酸酯基，亦可具有2個以上。其中，較佳為於兩末端具有異氰酸酯基之胺酯預聚物。 The moisture-curable amine ester resin may have only one isocyanate group in one molecule, or may have two or more. Among them, an amine ester prepolymer having an isocyanate group at both terminals is preferred.
上述胺酯預聚物可藉由使1分子中具有2個以上羥基之多元醇化合物與1分子中具有2個以上異氰酸酯基之聚異氰酸酯化合物反應而獲得。 The above-mentioned amine ester prepolymer can be obtained by reacting a polyol compound having two or more hydroxyl groups in one molecule with a polyisocyanate compound having two or more isocyanate groups in one molecule.
關於上述多元醇化合物與聚異氰酸酯化合物之反應，通常係於以多元醇化合物中之羥基(OH)與聚異氰酸酯化合物中之異氰酸酯基(NCO)之莫耳比計[NCO]/[OH]=2.0~2.5之範圍內進行。 The reaction of the above polyol compound with a polyisocyanate compound is usually carried out in a molar ratio of a hydroxyl group (OH) in a polyol compound to an isocyanate group (NCO) in a polyisocyanate compound [NCO] / [OH] = 2.0 Performed within the range of ~2.5.
作為上述多元醇化合物，可使用於聚胺酯之製造中通常使用之公知之多元醇化合物，例如可列舉：聚酯多元醇、聚醚多元醇、聚伸烷 基多元醇、聚碳酸酯多元醇等。該等多元醇化合物可單獨使用，亦可組合使用兩種以上。 As the above polyol compound, a known polyol compound which is generally used in the production of a polyurethane can be used, and examples thereof include polyester polyol, polyether polyol, and polyalkylene oxide. Base polyol, polycarbonate polyol, and the like. These polyol compounds may be used singly or in combination of two or more.
作為上述聚酯多元醇，例如可列舉：藉由多元羧酸與多元醇之反應而獲得之聚酯多元醇、或使ε-己內酯進行開環聚合而獲得之聚-ε-己內酯多元醇等。 Examples of the polyester polyol include a polyester polyol obtained by a reaction of a polyvalent carboxylic acid and a polyhydric alcohol, or a poly-ε-caprolactone obtained by ring-opening polymerization of ε-caprolactone. Polyols, etc.
作為成為上述聚酯多元醇之原料之上述多元羧酸，例如可列舉：對苯二甲酸、間苯二甲酸、1,5-萘二甲酸、2,6-萘二甲酸、琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、十亞甲基二羧酸、十二亞甲基二羧酸等。 Examples of the polyvalent carboxylic acid which is a raw material of the polyester polyol include terephthalic acid, isophthalic acid, 1,5-naphthalene dicarboxylic acid, 2,6-naphthalene dicarboxylic acid, succinic acid, and pentane. Acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decamethylene dicarboxylic acid, dodecamethylene dicarboxylic acid and the like.
作為成為上述聚酯多元醇之原料之上述多元醇，例如可列舉：乙二醇、丙二醇(propylene glycol)、1,3-丙二醇、1,4-丁二醇、新戊二醇、1,5-戊二醇、1,6-己二醇、二乙二醇、環己二醇等。 Examples of the polyhydric alcohol which is a raw material of the polyester polyol include ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, neopentyl glycol, and 1,5. - pentanediol, 1,6-hexanediol, diethylene glycol, cyclohexanediol, and the like.
作為上述聚醚多元醇，例如可列舉：乙二醇、丙二醇、四氫呋喃、3-甲基四氫呋喃之開環聚合物、及該等或其衍生物之無規共聚物或嵌段共聚物、或者雙酚型聚氧伸烷基改質體等。 Examples of the polyether polyol include a ring-opening polymer of ethylene glycol, propylene glycol, tetrahydrofuran, 3-methyltetrahydrofuran, and a random copolymer or block copolymer of the or a derivative thereof, or a double A phenolic polyoxyalkylene alkyl modified body or the like.
上述雙酚型聚氧伸烷基改質體係使雙酚型分子骨架之活性氫部分與環氧烷(例如環氧乙烷、環氧丙烷、環氧丁烷、環氧異丁烯等)進行加成反應而獲得之聚醚多元醇，可為無規共聚物，亦可為嵌段共聚物。 The above bisphenol type polyoxyalkylene alkylation system adds an active hydrogen moiety of a bisphenol type molecular skeleton to an alkylene oxide (for example, ethylene oxide, propylene oxide, butylene oxide, epoxy isobutylene, etc.) The polyether polyol obtained by the reaction may be a random copolymer or a block copolymer.
上述雙酚型聚氧伸烷基改質體較佳為於雙酚型分子骨架之兩末端加成有1種或2種以上之環氧烷。作為雙酚型，並無特別限定，可列舉：A型、F型、S型等，較佳為雙酚A型。 The bisphenol type polyoxyalkylene modified body preferably has one or more kinds of alkylene oxides added to both ends of the bisphenol type molecular skeleton. The bisphenol type is not particularly limited, and examples thereof include A type, F type, and S type, and a bisphenol A type is preferable.
作為上述聚伸烷基多元醇，例如可列舉：聚丁二烯多元醇、 氫化聚丁二烯多元醇、氫化聚異戊二烯多元醇等。 As the polyalkylene polyol, for example, a polybutadiene polyol, Hydrogenated polybutadiene polyol, hydrogenated polyisoprene polyol, and the like.
作為上述聚碳酸酯多元醇，例如可列舉：聚六亞甲基碳酸酯多元醇、聚環己二亞甲基碳酸酯多元醇等。 Examples of the polycarbonate polyol include polyhexamethylene carbonate polyol and polycyclohexane dimethylene carbonate polyol.
作為上述聚異氰酸酯化合物，例如可列舉：二苯基甲烷二異氰酸酯、二苯基甲烷二異氰酸酯之液狀改質物、聚合MDI(甲烷二異氰酸酯)、甲苯二異氰酸酯、萘-1,5-二異氰酸酯等。其中，就蒸氣壓或毒性較低之觀點、易處理性之觀點而言，較佳為二苯基甲烷二異氰酸酯及其改質物。上述聚異氰酸酯化合物可單獨使用，亦可組合使用兩種以上。 Examples of the polyisocyanate compound include diphenylmethane diisocyanate, a liquid modified product of diphenylmethane diisocyanate, polymerized MDI (methane diisocyanate), toluene diisocyanate, naphthalene-1,5-diisocyanate, and the like. . Among them, diphenylmethane diisocyanate and a modified product thereof are preferred from the viewpoint of low vapor pressure or low toxicity and ease of handling. These polyisocyanate compounds may be used singly or in combination of two or more.
又，上述濕氣硬化型胺酯樹脂較佳為使用具有下述式(1)所表示之結構之多元醇化合物而獲得者。藉由使用具有下述式(1)所表示之結構之多元醇化合物，可獲得接著性優異之組成物、或柔軟且延伸良好之硬化物，成為與上述自由基聚合性化合物之相溶性優異者。 Further, the moisture-curable amine ester resin is preferably obtained by using a polyol compound having a structure represented by the following formula (1). By using a polyol compound having a structure represented by the following formula (1), a composition excellent in adhesion or a cured product which is soft and excellent in elongation can be obtained, and the compatibility with the radical polymerizable compound is excellent. .
其中，較佳為使用由丙二醇、或四氫呋喃(THF)化合物之開環聚合化合物、或具有甲基等取代基之四氫呋喃化合物之開環聚合化合物所構成之聚醚多元醇。 Among them, a polyether polyol composed of a ring-opening polymerization compound of a propylene glycol or a tetrahydrofuran (THF) compound or a ring-opening polymerization compound of a tetrahydrofuran compound having a substituent such as a methyl group is preferably used.
式(1)中，R表示氫、甲基、或乙基，n為1~10之整數，L為0~5之整數，m為1~500之整數。n較佳為1~5，L較佳為0~4，m較佳為50~200。 In the formula (1), R represents hydrogen, a methyl group or an ethyl group, n is an integer of 1 to 10, L is an integer of 0 to 5, and m is an integer of 1 to 500. n is preferably from 1 to 5, L is preferably from 0 to 4, and m is preferably from 50 to 200.
再者，所謂L為0之情形，係指與R鍵結之碳直接與氧鍵結之情形。 In addition, the case where L is 0 means that the carbon bonded to R is directly bonded to oxygen.
進而，上述濕氣硬化型胺酯樹脂亦可具有自由基聚合性官能基。 Further, the moisture-curable amine ester resin may have a radical polymerizable functional group.
作為上述濕氣硬化型胺酯樹脂可具有之自由基聚合性官能基，較佳為具有不飽和雙鍵之基，尤其是就反應性之方面而言，更佳為(甲基)丙烯醯基。 The radically polymerizable functional group which the above-mentioned moisture-curable amine ester resin may have, preferably a group having an unsaturated double bond, and more preferably, in terms of reactivity, more preferably a (meth) acrylonitrile group .
再者，具有自由基聚合性官能基之濕氣硬化型胺酯樹脂不包含於自由基聚合性化合物中，係作為濕氣硬化型胺酯樹脂而處理。 Further, the moisture-curable amine ester resin having a radical polymerizable functional group is not contained in the radically polymerizable compound and is treated as a moisture-curable amine ester resin.
上述濕氣硬化型胺酯樹脂之重量平均分子量之較佳之下限為800，較佳之上限為1萬。若上述濕氣硬化型胺酯樹脂之重量平均分子量未達800，則存在交聯密度增高，柔軟性受損之情形。若上述濕氣硬化型胺酯樹脂之重量平均分子量超過1萬，則存在所獲得之光與濕氣硬化型樹脂組成物成為塗佈性較差者之情形。上述濕氣硬化型胺酯樹脂之重量平均分子量之更佳之下限為2000，更佳之上限為8000，進而較佳之下限為3000，進而較佳之上限為6000。 A preferred lower limit of the weight average molecular weight of the above moisture-curable amine ester resin is 800, and a preferred upper limit is 10,000. When the weight average molecular weight of the moisture-curable amine ester resin is less than 800, the crosslinking density is increased and the flexibility is impaired. When the weight average molecular weight of the moisture-curable urethane resin exceeds 10,000, the obtained light and the moisture-curable resin composition may be inferior in coatability. A lower limit of the weight average molecular weight of the above moisture-curable amine ester resin is preferably 2,000, more preferably 8,000, still more preferably 3,000, and still more preferably 6,000.
再者，於本說明書中，上述重量平均分子量係藉由凝膠滲透層析法(GPC)進行測定，並藉由聚苯乙烯換算而求出之值。作為藉由GPC測定利用聚苯乙烯換算之重量平均分子量時之管柱，例如可列舉Shodex LF-804(昭和電工公司製造)等。又，作為GPC中所使用之溶劑，可列舉四氫呋喃等。 In the present specification, the weight average molecular weight is measured by gel permeation chromatography (GPC) and is determined by polystyrene conversion. As a column for measuring the weight average molecular weight in terms of polystyrene by GPC, for example, Shodex LF-804 (manufactured by Showa Denko Co., Ltd.) or the like can be mentioned. Further, examples of the solvent used in GPC include tetrahydrofuran and the like.
關於上述濕氣硬化型胺酯樹脂之含量，相對於上述自由基聚合性化合物與上述濕氣硬化型胺酯樹脂之合計100重量份，較佳之下限為20重量份，較佳之上限為90重量份。若上述濕氣硬化型胺酯樹脂之含量未 達20重量份，則存在所獲得之光與濕氣硬化型樹脂組成物成為濕氣硬化性較差者之情形。若上述濕氣硬化型胺酯樹脂之含量超過90重量份，則存在所獲得之光與濕氣硬化型樹脂組成物成為光硬化性較差者之情形。上述濕氣硬化型胺酯樹脂之含量之更佳之下限為30重量份，更佳之上限為75重量份，進而較佳之下限為41重量份，進而較佳之上限為70重量份。 The content of the moisture-curable urethane resin is preferably 20 parts by weight, preferably 90 parts by weight, based on 100 parts by weight of the total of the radical polymerizable compound and the moisture-curable urethane resin. . If the content of the above moisture-curing amine ester resin is not When it is 20 parts by weight, the obtained light and moisture-curable resin composition may be inferior in moisture hardenability. When the content of the moisture-curable urethane resin exceeds 90 parts by weight, the obtained light and the moisture-curable resin composition may be inferior in photocurability. A more preferred lower limit of the content of the above moisture-curable amine ester resin is 30 parts by weight, more preferably an upper limit of 75 parts by weight, still more preferably a lower limit of 41 parts by weight, and still more preferably an upper limit of 70 parts by weight.
本發明之光與濕氣硬化型樹脂組成物含有光自由基聚合起始劑。 The light and moisture-curable resin composition of the present invention contains a photoradical polymerization initiator.
作為上述光自由基聚合起始劑，例如可列舉：二苯甲酮系化合物、苯乙酮系化合物、醯基氧化膦系化合物、二茂鈦系化合物、肟酯系化合物、安息香醚系化合物、9-氧硫等，就可獲得光硬化性(深部硬化性)尤其優異之組成物之觀點而言，較佳為醯基氧化膦系化合物。又，上述光自由基聚合起始劑較佳為如上所述般藉由照射370~450nm之波長區域之光而可感光者。 Examples of the photoradical polymerization initiator include a benzophenone compound, an acetophenone compound, a fluorenyl phosphine oxide compound, a titanocene compound, an oxime ester compound, and a benzoin ether compound. 9-oxygen sulfur In view of the fact that a composition having particularly excellent photocurability (deep curing property) can be obtained, a fluorenylphosphine oxide-based compound is preferable. Further, it is preferable that the photoradical polymerization initiator is photoreceptor by irradiating light of a wavelength region of 370 to 450 nm as described above.
作為上述醯基氧化膦系化合物，例如可列舉：雙(2,4,6-三甲基苯甲醯基)-苯基氧化膦、2,4,6-三甲基苯甲醯基二苯基氧化膦等。 Examples of the above fluorenyl phosphine oxide-based compound include bis(2,4,6-trimethylbenzylidene)-phenylphosphine oxide and 2,4,6-trimethylbenzhydrylbiphenyl. Phosphine oxide and the like.
作為上述光自由基聚合起始劑中之市售者，例如可列舉：IRGACURE 184、IRGACURE 369、IRGACURE 379、IRGACURE 651、IRGACURE 784、IRGACURE 819、IRGACURE 907、IRGACURE 2959、IRGACURE 4265、IRGACURE OXE01、Lucirin TPO、(均為BASF Japan公司製造)、安息香甲醚、安息香乙醚、安息香異丙醚(均為東京化成工業公司製造)等。 As a commercial one of the above-mentioned photoradical polymerization initiators, for example, IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 784, IRGACURE 819, IRGACURE 907, IRGACURE 2959, IRGACURE 4265, IRGACURE OXE01, Lucirin TPO, (both manufactured by BASF Japan), benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether (all manufactured by Tokyo Chemical Industry Co., Ltd.).
關於上述光自由基聚合起始劑之含量，相對於上述自由基聚 合性化合物100重量份，較佳之下限為0.01重量份，較佳之上限為10重量份。若上述光自由基聚合起始劑之含量未達0.01重量份，則存在無法使所獲得之光與濕氣硬化型樹脂組成物充分地進行光硬化之情形。若上述光自由基聚合起始劑之含量超過10重量份，則存在所獲得之光與濕氣硬化型樹脂組成物之保存穩定性降低之情形。上述光自由基聚合起始劑之含量之更佳之下限為0.1重量份，更佳之上限為5重量份。 Regarding the content of the above photoradical polymerization initiator, relative to the above-mentioned radical polymerization The compound has a lower limit of 0.01 parts by weight, preferably 10 parts by weight, preferably 10 parts by weight. When the content of the photoradical polymerization initiator is less than 0.01 part by weight, the obtained light and the moisture-curable resin composition may not be sufficiently photocured. When the content of the photoradical polymerization initiator is more than 10 parts by weight, the storage stability of the obtained light and the moisture-curable resin composition may be lowered. A more preferred lower limit of the content of the above photoradical polymerization initiator is 0.1 part by weight, and a more preferred upper limit is 5 parts by weight.
本發明之光與濕氣硬化型樹脂組成物亦可含有敏化劑。 The light and moisture-curable resin composition of the present invention may further contain a sensitizer.
本發明之光與濕氣硬化型樹脂組成物藉由含有上述敏化劑，可獲得高感度且光硬化性優異之光與濕氣硬化型樹脂組成物。上述敏化劑較佳為如上所述般藉由照射370~450nm之波長區域之光而發揮出增感效果者。 In the light-and-moisture-curing resin composition of the present invention, a light-sensitive and moisture-curable resin composition having high sensitivity and excellent photocurability can be obtained by containing the sensitizer. It is preferable that the sensitizer exhibits a sensitizing effect by irradiating light of a wavelength region of 370 to 450 nm as described above.
關於上述敏化劑，就較佳為於紫外、可見區域中具有充分之光吸收帶之方面而言，較佳為含有具有選自由二苯甲酮骨架、蒽骨架、蒽醌骨架、香豆素骨架、9-氧硫骨架、及酞青骨架所組成之群中之至少一種骨架之化合物，更佳為含有具有選自由蒽骨架、及蒽醌骨架、9-氧硫骨架所組成之群中之至少一種骨架之化合物。該等化合物亦可用作上述光自由基聚合起始劑。 With respect to the above sensitizer, it is preferred to have a sufficient light absorbing band in the ultraviolet and visible regions, preferably containing a benzophenone skeleton, an anthracene skeleton, an anthracene skeleton, and a coumarin. Skeleton, 9-oxosulfur a compound of at least one of a skeleton and a skeleton of the indigo skeleton, more preferably having a structure selected from the group consisting of an anthracene skeleton, an anthracene skeleton, and 9-oxosulfur a compound of at least one of the skeletons of the skeleton. These compounds can also be used as the above photoradical polymerization initiator.
作為上述具有二苯甲酮骨架之化合物，例如可列舉：二苯甲酮、2,4-二氯二苯甲酮、4,4'-雙(二甲基胺基)二苯甲酮、4,4'-雙(二乙基胺基)二苯甲酮等。 Examples of the compound having a benzophenone skeleton include benzophenone, 2,4-dichlorobenzophenone, and 4,4'-bis(dimethylamino)benzophenone, and 4 , 4'-bis(diethylamino)benzophenone and the like.
作為上述具有蒽骨架之化合物，例如可列舉：9,10-二丁氧基蒽、9,10-二丙氧基蒽醌、9,10-乙氧基蒽醌等。 Examples of the compound having an anthracene skeleton include 9,10-dibutoxyanthracene, 9,10-dipropoxyanthracene, and 9,10-ethoxyanthracene.
作為上述具有蒽醌骨架之化合物，例如可列舉：2-乙基蒽醌、1-甲 基蒽醌、1,4-二羥基蒽醌、2-(2-羥基乙氧基)-蒽醌等。 Examples of the compound having an anthracene skeleton include 2-ethyl hydrazine and 1-methyl group. Base, 1,4-dihydroxyindole, 2-(2-hydroxyethoxy)-indole, and the like.
作為上述具有香豆素骨架之化合物，例如可列舉7-二乙基胺基-4-甲基香豆素等。 The compound having a coumarin skeleton may, for example, be 7-diethylamino-4-methylcoumarin or the like.
作為上述具有9-氧硫骨架之化合物，例如可列舉：2,4-二乙基9-氧硫、2-氯9-氧硫、4-異丙基9-氧硫、1-氯-4-丙基9-氧硫等。 As the above, having 9-oxosulfur The compound of the skeleton may, for example, be 2,4-diethyl 9-oxosulfur 2-chloro 9-oxosulfur 4-isopropyl 9-oxosulfur 1-chloro-4-propyl 9-oxosulfur Wait.
作為上述具有酞青骨架之化合物，例如可列舉酞青等。 Examples of the compound having a phthalocyanine skeleton include indigo and the like.
該等敏化劑之中，就所獲得之光與濕氣硬化型樹脂組成物成為遮光部之硬化性尤其優異者之觀點而言，可較佳地使用4,4'-雙(二甲基胺基)二苯甲酮及4,4'-雙(二乙基胺基)二苯甲酮之至少任一者。 Among these sensitizers, 4,4'-bis(dimethyl group) is preferably used from the viewpoint that the light-curable resin composition obtained is a particularly excellent hardenability of the light-shielding portion. At least one of an amino) benzophenone and 4,4'-bis(diethylamino)benzophenone.
關於上述敏化劑之含量，相對於上述光聚合起始劑100重量份，較佳之下限為2量份，較佳之上限為50重量份。若上述敏化劑之含量未達2重量份，則存在未充分地發揮出增感效果之情形。若上述敏化劑之含量超過50重量份，則存在所獲得之光與濕氣硬化型樹脂組成物之保存穩定性降低之情形。上述敏化劑之含量之更佳之下限為5重量份，更佳之上限為40重量份。 The content of the sensitizer is preferably 2 parts by weight, and preferably 50 parts by weight, based on 100 parts by weight of the photopolymerization initiator. When the content of the sensitizer is less than 2 parts by weight, the sensitizing effect may not be sufficiently exhibited. When the content of the sensitizer exceeds 50 parts by weight, the storage stability of the obtained light and the moisture-curable resin composition may be lowered. A more preferred lower limit of the content of the above sensitizer is 5 parts by weight, and a more preferred upper limit is 40 parts by weight.
關於本發明之光與濕氣硬化型樹脂組成物，就調整所獲得之光與濕氣硬化型樹脂組成物之塗佈性或形狀保持性等觀點而言，亦可含有填充劑。藉由含有上述填充劑，本發明之光與濕氣硬化型樹脂組成物成為具有較佳之搖變性者，可充分地保持塗佈後之形狀。 The light-and-moisture-curing resin composition of the present invention may contain a filler from the viewpoints of adjusting the coatability and shape retention of the light and the moisture-curable resin composition obtained. By containing the above filler, the light-and-moisture-curing resin composition of the present invention has a preferable shaker property, and the shape after coating can be sufficiently maintained.
上述填充劑之一次粒徑之較佳之下限為1nm，較佳之上限為50nm。若上述填充劑之一次粒徑未達1nm，則存在所獲得之光與濕氣硬 化型樹脂組成物成為塗佈性較差者之情形。若上述填充劑之一次粒徑超過50nm，則存在所獲得之光與濕氣硬化型樹脂組成物成為塗佈後之形狀保持性較差者之情形。上述填充劑之一次粒徑之更佳之下限為5nm，更佳之上限為30nm，進而較佳之下限為10nm，進而較佳之上限為20nm。 A preferred lower limit of the primary particle diameter of the above filler is 1 nm, and a preferred upper limit is 50 nm. If the primary particle diameter of the above filler is less than 1 nm, the obtained light and moisture are hard. The chemical resin composition is in a case where the coatability is poor. When the primary particle diameter of the filler exceeds 50 nm, the obtained light and the moisture-curable resin composition may be inferior in shape retention after coating. A lower limit of the primary particle diameter of the above filler is 5 nm, more preferably 30 nm, and further preferably a lower limit of 10 nm, and further preferably an upper limit of 20 nm.
再者，上述填充劑之一次粒徑可使用NICOMP 380ZLS(PARTICLE SIZING SYSTEMS公司製造)，使上述填充劑分散於溶劑(水、有機溶劑等)中而進行測定。 In addition, the primary particle diameter of the above-mentioned filler can be measured by dispersing the above-mentioned filler in a solvent (water, an organic solvent, etc.) using NICOMP 380ZLS (manufactured by PARTICLE SIZING SYSTEMS).
又，上述填充劑存在於本發明之光與濕氣硬化型樹脂組成物中以二次粒子(複數個一次粒子聚集而成者)之形式存在之情形，此種二次粒子之粒徑之較佳之下限為5nm，較佳之上限為500nm，更佳之下限為10nm，更佳之上限為100nm。上述填充劑之二次粒子之粒徑可藉由使用穿透式電子顯微鏡(TEM)對本發明之光與濕氣硬化型樹脂組成物或其硬化物進行觀察而測定。 Further, the above-mentioned filler is present in the form of secondary particles (a plurality of primary particles aggregated) in the light-and-moisture-curing resin composition of the present invention, and the particle diameter of such secondary particles is relatively The lower limit is preferably 5 nm, preferably the upper limit is 500 nm, more preferably the lower limit is 10 nm, and the more preferred upper limit is 100 nm. The particle diameter of the secondary particles of the above filler can be measured by observing the light and moisture-curable resin composition of the present invention or a cured product thereof using a transmission electron microscope (TEM).
作為上述填充劑，較佳為無機填充劑，例如可列舉：二氧化矽、滑石、氧化鈦、氧化鋅、碳酸鈣等。其中，就所獲得之光與濕氣硬化型樹脂組成物成為UV光透過性優異者之觀點而言，較佳為二氧化矽。該等填充劑可單獨使用，亦可組合使用兩種以上。 The filler is preferably an inorganic filler, and examples thereof include cerium oxide, talc, titanium oxide, zinc oxide, and calcium carbonate. Among them, in view of the fact that the obtained light and moisture-curable resin composition are excellent in UV light transmittance, cerium oxide is preferred. These fillers may be used singly or in combination of two or more.
上述填充劑較佳為進行疏水性表面處理。藉由上述疏水性表面處理，所獲得之光與濕氣硬化型樹脂組成物成為塗佈後之形狀保持性更優異者。 The above filler is preferably subjected to a hydrophobic surface treatment. By the above hydrophobic surface treatment, the obtained light and moisture-curable resin composition are more excellent in shape retention after coating.
作為上述疏水性表面處理，可列舉：矽烷化處理、烷基化處理、環氧化處理等。其中，就提高形狀保持性之效果優異之觀點而言，較佳為矽烷 化處理，更佳為三甲基矽烷化處理。 Examples of the hydrophobic surface treatment include a decaneization treatment, an alkylation treatment, and an epoxidation treatment. Among them, from the viewpoint of excellent effect of improving shape retention, decane is preferred. The treatment is more preferably trimethyl decane treatment.
作為對上述填充劑進行疏水性表面處理之方法，例如可列舉使用矽烷偶合劑等表面處理劑，對填充劑之表面進行處理之方法等。 The method of performing the hydrophobic surface treatment on the above-mentioned filler may, for example, be a method of treating the surface of the filler by using a surface treatment agent such as a decane coupling agent.
具體而言，例如，上述三甲基矽烷化處理二氧化矽例如可藉由如下方法等進行製作：藉由溶膠凝膠法等方法合成二氧化矽，於使二氧化矽流動之狀態下霧狀噴出六甲基二矽氮烷之方法；或者於醇、甲苯等有機溶劑中添加二氧化矽，進而，於添加六甲基二矽氮烷與水後，利用蒸發器使水與有機溶劑蒸發乾燥之方法。 Specifically, for example, the above-described trimethylsulfonation-treated cerium oxide can be produced, for example, by synthesizing cerium oxide by a method such as a sol-gel method or in the form of a mist in a state in which cerium oxide flows. a method of ejecting hexamethyldioxane; or adding cerium oxide to an organic solvent such as an alcohol or toluene, and further, after adding hexamethyldioxane and water, evaporating and drying the water and the organic solvent by using an evaporator; The method.
關於上述填充劑之含量，於本發明之光與濕氣硬化型樹脂組成物整體100重量份中，較佳之下限為0.1重量份，較佳之上限為20重量份。若上述填充劑之含量未達0.1重量份，則存在所獲得之光與濕氣硬化型樹脂組成物成為塗佈後之形狀保持性較差者之情形。若上述填充劑之含量超過20重量份，則存在所獲得之光與濕氣硬化型樹脂組成物成為塗佈性較差者之情形。上述填充劑之含量之更佳之下限為0.5重量份，更佳之上限為15重量份，進而較佳之下限為1重量份，進而較佳之上限為12重量份，尤佳之下限為2重量份。 The content of the above-mentioned filler is preferably 0.1 part by weight, and preferably 20 parts by weight, based on 100 parts by weight of the total of the light- and moisture-curable resin composition of the present invention. When the content of the filler is less than 0.1 part by weight, the obtained light and the moisture-curable resin composition may be inferior in shape retention after coating. When the content of the above filler is more than 20 parts by weight, the obtained light and the moisture-curable resin composition may be inferior in coatability. A more preferred lower limit of the content of the above filler is 0.5 parts by weight, more preferably 15 parts by weight, still more preferably 1 part by weight, still more preferably 12 parts by weight, and even more preferably 2 parts by weight.
本發明之光與濕氣硬化型樹脂組成物進而亦可視需要含有離子液體、溶劑、含金屬之粒子、反應性稀釋劑等添加劑。 The light-and-moisture-curing resin composition of the present invention may further contain an additive such as an ionic liquid, a solvent, a metal-containing particle, or a reactive diluent, as needed.
作為製造本發明之光與濕氣硬化型樹脂組成物之方法，例如可列舉如下方法等：使用勻相分散機、均質攪拌機、萬能攪拌機、行星式攪拌機、捏合機、三輥研磨機等混合機，將自由基聚合性化合物、濕氣硬化型胺酯樹脂、光自由基聚合起始劑、遮光劑、及視需要添加之添加劑進 行混合。 As a method of producing the light-and-moisture-curing resin composition of the present invention, for example, a method such as a homogeneous phase disperser, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three-roll mill can be used. a radical polymerizable compound, a moisture-curing amine ester resin, a photoradical polymerization initiator, an opacifier, and an additive to be added as needed Line mixing.
本發明之光與濕氣硬化型樹脂組成物可藉由利用光照射迅速地進行硬化，進而使之濕氣硬化而使之充分地硬化。 The light-and-moisture-curing resin composition of the present invention can be sufficiently cured by being rapidly hardened by light irradiation and then hardened by moisture.
再者，作為使本發明之光與濕氣硬化型樹脂組成物進行光硬化時使用之光源，不僅可使用通常所使用之高壓水銀燈或金屬鹵化物燈，亦可使用LED方式之光源。 Further, as a light source used for photocuring the light and moisture-curable resin composition of the present invention, not only a high-pressure mercury lamp or a metal halide lamp which is usually used but also a light source of an LED type can be used.
關於本發明之光與濕氣硬化型樹脂組成物，硬化後之1mm厚度之硬化物之光學密度(OD值)較佳為1以上。若上述OD值未達1，則存在遮光性變得不充分，於用於顯示元件中之情形時發生漏光，而無法獲得較高之對比度之情形。上述OD值更佳為1.5以上。 In the light-and-moisture-curing resin composition of the present invention, the optical density (OD value) of the cured product having a thickness of 1 mm after curing is preferably 1 or more. When the OD value is less than 1, the light-shielding property is insufficient, and when it is used in a display element, light leakage occurs, and a high contrast cannot be obtained. The above OD value is more preferably 1.5 or more.
上述OD值越高越佳，但若為了提高上述OD值而過多地摻合遮光劑，則會產生因增黏所引起之作業性之降低等，故而為了保持與遮光劑之摻合量之平衡性，上述硬化體之OD值之較佳之上限為4。 The higher the OD value, the better. However, if the opaque agent is excessively blended in order to increase the OD value, workability due to viscosity increase or the like may occur, so that the balance with the amount of the opacifier is maintained. Preferably, the upper limit of the OD value of the hardened body is 4.
再者，上述光與濕氣硬化型樹脂組成物之硬化後之OD值可使用光學密度計進行測定。測定上述OD值之硬化物可藉由使用高壓水銀燈等，照射500mJ/cm2之紫外線而獲得。 Further, the OD value after curing of the light and moisture-curable resin composition can be measured using an optical densitometer. The cured product having the above OD value can be obtained by irradiating ultraviolet rays of 500 mJ/cm 2 using a high pressure mercury lamp or the like.
本發明之光與濕氣硬化型樹脂組成物之使用錐板型黏度計於25℃、1rpm的條件下測得之黏度之較佳之下限為50Pa．s，較佳之上限為500Pa．s。若上述黏度未達50Pa．s或超過500Pa．s，則存在於將光與濕氣硬化型樹脂組成物用於電子零件用接著劑或顯示元件用接著劑中之情形時，塗佈於基板等被接著體時之作業性變差之情形。上述黏度之更佳之下限為80Pa．s，更佳之上限為300Pa．s，進而較佳之上限為200Pa．s。 The lower limit of the viscosity of the light and moisture-curable resin composition of the present invention measured by a cone-and-plate type viscometer at 25 ° C and 1 rpm is 50 Pa. s, the upper limit is preferably 500Pa. s. If the above viscosity is less than 50Pa. s or more than 500Pa. In the case where the light and moisture-curable resin composition is used for an adhesive for an electronic component or an adhesive for a display element, the workability when applied to a member such as a substrate is deteriorated. The lower limit of the above viscosity is 80 Pa. s, the upper limit is 300Pa. s, and thus the upper limit is preferably 200 Pa. s.
本發明之光與濕氣硬化型樹脂組成物之搖變指數之較佳之下限為1.3，較佳之上限為5.0。若上述搖變指數未達1.3或超過5.0，則存在於將光與濕氣硬化型樹脂組成物用於電子零件用接著劑或顯示元件用接著劑中之情形時，塗佈於基板等被接著體時之作業性變差之情形。上述搖變指數之更佳之下限為1.5，更佳之上限為4.0。 A preferred lower limit of the rocking index of the light- and moisture-curable resin composition of the present invention is 1.3, and a preferred upper limit is 5.0. When the above-mentioned rocking index is less than 1.3 or exceeds 5.0, when the light and moisture-curable resin composition is used in an adhesive for an electronic component or an adhesive for a display element, application to a substrate or the like is performed. The situation in which the workability of the body is deteriorated. A lower limit of the above-mentioned rocking index is 1.5, and a lower limit is 4.0.
再者，於本說明書中，上述所謂搖變指數，係指將使用錐板型黏度計於25℃、1rpm之條件下測得之黏度除以使用錐板型黏度計於25℃、10rpm之條件下測得之黏度而得的值。 In addition, in the present specification, the above-mentioned so-called rocking index means that the viscosity measured by using a cone-and-plate type viscometer at 25 ° C and 1 rpm is divided by a cone-plate type viscometer at 25 ° C and 10 rpm. The value obtained by measuring the viscosity.
本發明之光與濕氣硬化型樹脂組成物可尤佳地用作電子零件用接著劑或顯示元件用接著劑。使用本發明之光與濕氣硬化型樹脂組成物而成之電子零件用接著劑、及使用本發明之光與濕氣硬化型樹脂組成物而成之顯示元件用接著劑亦分別為本發明之一。 The light-and-moisture-curing resin composition of the present invention can be preferably used as an adhesive for electronic parts or an adhesive for display elements. The adhesive for electronic components obtained by using the light-and-moisture-curing resin composition of the present invention and the adhesive for display elements using the light-and-moisture-curing resin composition of the present invention are also the present inventions. One.
根據本發明，可提供一種遮光性及接著性優異之光與濕氣硬化型樹脂組成物。 According to the present invention, it is possible to provide a light-and-moisture-curing resin composition which is excellent in light-shielding property and adhesion property.
1‧‧‧聚碳酸酯樹脂基板 1‧‧‧ polycarbonate resin substrate
2‧‧‧光與濕氣硬化型樹脂組成物 2‧‧‧Light and moisture hardening resin composition
3‧‧‧玻璃板 3‧‧‧ glass plate
圖1(a)係表示自上方觀察接著性之評價用樣品之情形之模式圖，圖1(b)係表示自側面觀察接著性之評價用樣品之情形之模式圖。 Fig. 1(a) is a schematic view showing a state in which a sample for evaluation of adhesion is observed from above, and Fig. 1(b) is a schematic view showing a state in which a sample for evaluation of adhesion is observed from the side.
以下列舉實施例更詳細地說明本發明，但本發明並不僅限定 於該等實施例。又，根據本發明，可提供一種使用該光與濕氣硬化型樹脂組成物而成之電子零件用接著劑及顯示元件用接著劑。 The invention will be described in more detail below by way of examples, but the invention is not limited thereto In these embodiments. Moreover, according to the present invention, an adhesive for an electronic component and an adhesive for a display element which are obtained by using the light and moisture-curable resin composition can be provided.
將作為多元醇之100重量份聚四亞甲醚二醇(三菱化學公司製造，「PTMG-2000」)、及0.01重量份之二月桂酸二丁基錫添加至500mL容積之可分離式燒瓶中，於真空下(20mmHg以下)、100℃攪拌30分鐘而進行混合。其後，設為常壓，添加作為二異氰酸酯之26.5重量份之Pure MDI(日曹商事公司製造)，於80℃攪拌3小時，使之反應，而獲得胺酯預聚物A(重量平均分子量2700)。 100 parts by weight of polytetramethylene ether glycol ("MGMG-2000", manufactured by Mitsubishi Chemical Corporation), and 0.01 part by weight of dibutyltin dilaurate, as a polyol, were added to a 500 mL volume separable flask. The mixture was stirred under vacuum (20 mmHg or less) at 100 ° C for 30 minutes. Then, as a normal pressure, 26.5 parts by weight of Pure MDI (manufactured by Rixo Co., Ltd.) as a diisocyanate was added, and the mixture was stirred at 80 ° C for 3 hours to cause an amine ester prepolymer A (weight average molecular weight). 2700).
將作為多元醇之100重量份之聚丙二醇(旭硝子公司製造，「EXCENOL 2020」)、及0.01重量份之二月桂酸二丁基錫添加至500mL容積之可分離式燒瓶中，於真空下(20mmHg以下)、100℃攪拌30分鐘而進行混合。其後，設為常壓，添加作為二異氰酸酯之26.5重量份之Pure MDI(日曹商事公司製造)，於80℃攪拌3小時，使之反應，而獲得胺酯預聚物B(重量平均分子量2900)。 100 parts by weight of polypropylene glycol ("EXCENOL 2020" manufactured by Asahi Glass Co., Ltd.) and 0.01 part by weight of dibutyltin dilaurate were added to a 500 mL separable flask under vacuum (20 mmHg or less). The mixture was stirred at 100 ° C for 30 minutes to carry out mixing. Then, as a normal pressure, 26.5 parts by weight of Pure MDI (manufactured by Rixo Co., Ltd.) as a diisocyanate was added, and the mixture was stirred at 80 ° C for 3 hours to obtain an amine ester prepolymer B (weight average molecular weight). 2900).
於添加有以與合成例1相同之方式獲得之胺酯預聚物A之反應容器中，添加甲基丙烯酸羥基乙酯1.3重量份、及作為聚合抑制劑之N-亞硝基苯基羥基胺鋁鹽(和光純藥工業公司製造，「Q-1301」)0.14重量份，於氮氣氣流下、80℃攪拌混合1小時，而獲得於分子末端具有異氰酸酯基與甲基丙烯醯基之胺酯預聚物C(重量平均分子量3100)。 To a reaction vessel to which the amine ester prepolymer A obtained in the same manner as in Synthesis Example 1 was added, 1.3 parts by weight of hydroxyethyl methacrylate was added, and N-nitrosophenylhydroxylamine as a polymerization inhibitor was added. 0.14 parts by weight of aluminum salt ("Q-1301" manufactured by Wako Pure Chemical Industries, Ltd.), and stirred and mixed at 80 ° C for 1 hour under a nitrogen gas stream to obtain an amine ester having an isocyanate group and a methacryl oxime group at the molecular terminal. Polymer C (weight average molecular weight 3100).
依據表1、2中記載之摻合比，利用行星式攪拌裝置(Thinky公司製造，「脫泡練太郎」)攪拌各材料後，利用陶瓷三輥研磨機均勻地進行混合，而獲得實施例1~16，比較例1、2之光與濕氣硬化型樹脂組成物。 According to the blending ratios shown in Tables 1 and 2, each material was stirred by a planetary stirring device (manufactured by Thinky Co., Ltd., "Defoaming Taro"), and then uniformly mixed by a ceramic three-roll mill to obtain Example 1 ~16, the light and moisture-curable resin compositions of Comparative Examples 1 and 2.
再者，表1中之「胺酯預聚物A」為合成例1中記載之於兩末端具有異氰酸酯基之胺酯預聚物，「胺酯預聚物B」為合成例2中記載之於兩末端具有異氰酸酯基之胺酯預聚物，「胺酯預聚物C」為合成例3中記載之於分子末端具有異氰酸酯基與甲基丙烯醯基之胺酯預聚物。 In addition, the "amine ester prepolymer A" in Table 1 is an amine ester prepolymer having an isocyanate group at both terminals described in Synthesis Example 1, and the "amine ester prepolymer B" is described in Synthesis Example 2. The amine ester prepolymer having an isocyanate group at both ends, and the "amine ester prepolymer C" is an amine ester prepolymer having an isocyanate group and a methacryl oxime group at the molecular terminal described in Synthesis Example 3.
對實施例及比較例中獲得之各光與濕氣硬化型樹脂組成物進行以下之評價。將結果示於表1、2。 Each of the light and moisture-curable resin compositions obtained in the examples and the comparative examples was evaluated as follows. The results are shown in Tables 1 and 2.
將實施例及比較例中獲得之各光與濕氣硬化型樹脂組成物塗佈於以1mm厚度之鐵氟龍(註冊商標)小片作為間隙劑之脫模聚對苯二甲酸乙二酯(PET)上，於其上進而重疊脫模PET，利用玻璃按壓而成為均勻之厚度後，使用高壓水銀燈，照射500mJ/cm2之紫外線，藉此使光與濕氣硬化型樹脂組成物光硬化。 Each of the light and moisture-curable resin compositions obtained in the examples and the comparative examples was applied to a release-type polyethylene terephthalate (PET) having a Teflon (registered trademark) piece having a thickness of 1 mm as a gap agent. Further, the release PET was further superposed thereon, and the glass was pressed to have a uniform thickness. Then, a high-pressure mercury lamp was used to irradiate ultraviolet rays of 500 mJ/cm 2 to light-cure the light and the moisture-curable resin composition.
其後，放置一夜，藉此使之進行濕氣硬化，而獲得1mm厚度之遮光性評價用樣品。 Thereafter, it was left overnight to be subjected to moisture hardening to obtain a sample for light-shielding evaluation of 1 mm thickness.
對所獲得之遮光性評價用樣品，使用光學密度計(X-rite公司製造，「光譜儀」)測定光學密度(OD值)。 The optical density (OD value) of the obtained sample for light-shielding evaluation was measured using an optical densitometer ("Spectrometer" by X-rite Co., Ltd.).
使用分配裝置，以約2mm之寬度將實施例及比較例中獲得之各光與濕氣硬化型樹脂組成物塗佈於聚碳酸酯基板上。其後，使用高壓水銀燈，照射500mJ/cm2之紫外線，藉此使光與濕氣硬化型樹脂組成物光硬化。 Each of the light and moisture-curable resin compositions obtained in the examples and the comparative examples was applied onto a polycarbonate substrate at a width of about 2 mm using a dispensing device. Thereafter, the high-pressure mercury lamp was used to irradiate ultraviolet rays of 500 mJ/cm 2 to photoharden the light and the moisture-curable resin composition.
其後，將玻璃板貼合於聚碳酸酯基板上，並放置一夜，藉此使之進行濕氣硬化，而獲得接著性評價用樣品。 Thereafter, the glass plate was bonded to a polycarbonate substrate and allowed to stand overnight to be subjected to moisture hardening to obtain a sample for adhesion evaluation.
圖1中表示自上方觀察接著性評價用樣品之情形之模式圖(圖1(a))、及表示自側面觀察接著性評價用樣品之情形之模式圖(圖1(b))。 Fig. 1 is a schematic view showing a state in which a sample for adhesion evaluation is observed from above (Fig. 1 (a)), and a schematic view showing a state in which a sample for adhesion evaluation is observed from the side (Fig. 1 (b)).
使用拉伸試驗機，於剪切方向上以5mm/sec之速度拉伸所製作之接著性評價用樣品，並測定基材剝離時之強度。 The prepared sample for adhesion evaluation was stretched at a speed of 5 mm/sec in the shear direction using a tensile tester, and the strength at the time of peeling of the substrate was measured.
使用分配裝置，以約2mm之寬度將實施例及比較例中獲得之各光與濕氣硬化型樹脂組成物塗佈於聚碳酸酯基板上。其後，使用高壓水銀燈，照射500mJ/cm2之紫外線，藉此使光與濕氣硬化型樹脂組成物光硬化，而製作深部硬化性評價用樣品。於利用滲透有丙酮之不織布(旭化成纖維公司製造，「超低發塵拭巾(bemcot)」)擦拭所獲得之深部硬化性評價用樣品時，將整個硬化物容易自基板上脫落(未深部硬化)者評價為「×」，將硬化物之一部分殘留於基板上者(一部分經深部硬化)評價為「△」，將硬化物之大部分殘留於基板上者(大部分經深部硬化)評價為「○」，硬化物完全未自基板上脫落者(經深部硬化)評價為「◎」，而評價深部硬化性。 Each of the light and moisture-curable resin compositions obtained in the examples and the comparative examples was applied onto a polycarbonate substrate at a width of about 2 mm using a dispensing device. Thereafter, the high-pressure mercury lamp was used to irradiate ultraviolet rays of 500 mJ/cm 2 to photoharden the light and the moisture-curable resin composition, thereby preparing a sample for evaluation of deep curing property. When the sample for deep hardenability evaluation obtained by wiping off the nonwoven fabric impregnated with acetone ("bemcot" manufactured by Asahi Kasei Fiber Co., Ltd.) is used, the entire cured product is easily peeled off from the substrate (not deep hardened) The evaluation was "x", and one part of the cured product remained on the substrate (partially deep-hardened) was evaluated as "△", and most of the cured product remained on the substrate (mostly deep-hardened) was evaluated as "○", the cured product was evaluated as "◎" when it was not peeled off from the substrate at all, and the deep hardenability was evaluated.
根據本發明，可提供一種遮光性及接著性優異之光與濕氣硬化型樹脂組成物。又，根據本發明，可提供一種使用該光與濕氣硬化型樹脂組成物而成之電子零件用接著劑及顯示元件用接著劑。 According to the present invention, it is possible to provide a light-and-moisture-curing resin composition which is excellent in light-shielding property and adhesion property. Moreover, according to the present invention, an adhesive for an electronic component and an adhesive for a display element which are obtained by using the light and moisture-curable resin composition can be provided.
1‧‧‧聚碳酸酯樹脂基板 1‧‧‧ polycarbonate resin substrate
2‧‧‧光與濕氣硬化型樹脂組成物 2‧‧‧Light and moisture hardening resin composition
3‧‧‧玻璃板 3‧‧‧ glass plate
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| JP6510788B2 (en) * | 2014-10-03 | 2019-05-08 | 積水化学工業株式会社 | Light moisture curable resin composition |
| CN110105530B (en) * | 2019-05-10 | 2021-05-11 | 广州回天新材料有限公司 | Preparation method of UV (ultraviolet) moisture dual-curing resin |
| WO2023153514A1 (en) * | 2022-02-14 | 2023-08-17 | 積水化学工業株式会社 | Photo/moisture-curable resin composition, adhesive for electronic component, and adhesive for display element |
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