JP2005076017A - Photocurable resin composition - Google Patents
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- JP2005076017A JP2005076017A JP2003312084A JP2003312084A JP2005076017A JP 2005076017 A JP2005076017 A JP 2005076017A JP 2003312084 A JP2003312084 A JP 2003312084A JP 2003312084 A JP2003312084 A JP 2003312084A JP 2005076017 A JP2005076017 A JP 2005076017A
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- 239000011342 resin composition Substances 0.000 title claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 239000005062 Polybutadiene Substances 0.000 claims abstract description 8
- 229920002857 polybutadiene Polymers 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 6
- 229920001195 polyisoprene Polymers 0.000 claims abstract description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 5
- 239000003999 initiator Substances 0.000 claims abstract description 5
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims abstract description 4
- 229940119545 isobornyl methacrylate Drugs 0.000 claims abstract description 4
- 239000000178 monomer Substances 0.000 claims abstract description 4
- 239000000853 adhesive Substances 0.000 abstract description 49
- 230000001070 adhesive effect Effects 0.000 abstract description 49
- 238000000016 photochemical curing Methods 0.000 abstract description 4
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 238000001723 curing Methods 0.000 description 14
- 238000011156 evaluation Methods 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- -1 phosphate ester Chemical class 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- GIMQKKFOOYOQGB-UHFFFAOYSA-N 2,2-diethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)(OCC)C(=O)C1=CC=CC=C1 GIMQKKFOOYOQGB-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- 239000010960 cold rolled steel Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000004094 surface-active agent Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
【課題】充分に高い接着強さを有し、長期間高湿度下に放置された場合にも、接着強さの低下が極めて少なく、且つ接着剤硬化時に発生する内部応力が小さい光硬化性樹脂組成物を提供する。
【解決手段】分子内の主鎖骨格がポリブタジエン、ポリイソプレン又はその水素添加物のいずれか、又はその混合物からなり、両端又は側鎖に１個以上の（メタ）アクリロイル基を有する、プレポリマー、イソボルニルメタクリレート、下記化学式で表される（メタ）アクリレートモノマー、光重合開始剤を必須成分とする光硬化性樹脂組成物。
【化１】
【選択図】なしThe present invention relates to a photo-curing resin that has a sufficiently high adhesive strength, has a very low decrease in adhesive strength even when left under high humidity for a long period of time, and has a small internal stress generated when an adhesive is cured. A composition is provided.
A prepolymer in which a main chain skeleton in a molecule is made of polybutadiene, polyisoprene, a hydrogenated product thereof, or a mixture thereof, and has one or more (meth) acryloyl groups at both ends or side chains, A photocurable resin composition comprising, as essential components, isobornyl methacrylate, a (meth) acrylate monomer represented by the following chemical formula, and a photopolymerization initiator.
[Chemical 1]
[Selection figure] None
Description
本発明は、光硬化性樹脂組成物に関する。さらに、詳しくは高い接着強さを有し、耐湿性が良好であり、且つ、接着歪みの少ない光硬化性樹脂組成物に関する。 The present invention relates to a photocurable resin composition. More specifically, the present invention relates to a photocurable resin composition having high adhesive strength, good moisture resistance, and less adhesive distortion.
近年のオプトエレクトロニクス分野では、機器の高性能化に伴い、より接着強さが高く、耐湿性が良好な接着剤が求められている。又、光学部品のプラスチック化が進む中で、接着剤の硬化収縮等に起因する内部応力が被着体であるプラスチック部品に及ぼす影響は無視できず、接着歪みの少ない接着剤の開発が望まれている。 In the field of optoelectronics in recent years, with higher performance of devices, there is a demand for adhesives with higher adhesive strength and better moisture resistance. In addition, with the progress of plasticization of optical parts, the influence of internal stress caused by curing shrinkage of the adhesive on the plastic parts as adherends cannot be ignored, and the development of adhesives with less adhesive distortion is desired. ing.
耐水性の良好な接着剤組成物としては、特許文献１に防水用接着剤組成物が提案されている。本公報に例示されている接着剤組成物は、耐久後の引っ張り接着強度保持率が高いながら、いずれも強度が低下し、接着剤硬化時に発生する内部応力が大きい。
本発明の課題は、充分に高い接着強さを有し、耐久性、特に長期間高湿度下に放置された場合にも、接着強さの低下が極めて少なく、且つ接着剤硬化時に発生する内部応力が小さい光硬化性樹脂組成物を提供することである。 It is an object of the present invention to have a sufficiently high adhesive strength, durability, especially when left under high humidity for a long period of time, and the deterioration of the adhesive strength is extremely small, and the inside generated when the adhesive is cured It is to provide a photocurable resin composition having a low stress.
本発明の接着剤組成物は、次の（ａ）（ｂ）（ｃ）（ｄ）を含有する物である。
（ａ）分子内の主鎖骨格がポリブタジエン、ポリイソプレン又はその水素添加物のいずれか、又はその混合物からなり、両端又は側鎖に１個以上の（メタ）アクリロイル基を有する、分子量５００から５０００のプレポリマー３０〜７０質量部、
（ｂ）イソボルニルメタクリレート２０〜６０質量部、
（ｃ）下記化学式で表される（メタ）アクリレートモノマー１０〜４０質量部、
（ｄ）光重合開始剤。
(A) Molecular weight of 500 to 5000, in which the main chain skeleton in the molecule is composed of polybutadiene, polyisoprene or a hydrogenated product thereof, or a mixture thereof, and has one or more (meth) acryloyl groups at both ends or side chains. 30 to 70 parts by weight of a prepolymer of
(B) 20-60 parts by mass of isobornyl methacrylate,
(C) 10 to 40 parts by mass of a (meth) acrylate monomer represented by the following chemical formula,
(D) Photopolymerization initiator.
本発明の光硬化性樹脂組成物により初期に高い接着強さを有し、高湿度下での強度低下が極めて小さく、且つ接着剤硬化時に発生する内部応力の小さい接着剤が得られるため、接着剤の内部応力が影響する、プラスチック製光学材料のへの接着の適用が可能となる。 The photo-curable resin composition of the present invention has an initial high adhesive strength, an extremely low decrease in strength under high humidity, and an adhesive having a low internal stress generated when the adhesive is cured. It is possible to apply an adhesive to a plastic optical material affected by the internal stress of the agent.
本発明では、成分（ａ）として、分子内の主鎖骨格がポリブタジエン、ポリイソプレン又はその水素添加物のいずれか、又はその混合物からなり、末端又は側鎖に１個以上の（メタ）アクリロイル基を有する、分子量５００から５０００のプレポリマーが３０〜７０質量部添加される。成分（ａ）の添加量が、３０質量部未満では、接着剤硬化時の内部応力が大きくなる可能性があり、又７０質量部を超えると、初期に充分な接着強さが得られない可能性がある。 In the present invention, as the component (a), the main chain skeleton in the molecule is either polybutadiene, polyisoprene or a hydrogenated product thereof, or a mixture thereof, and has one or more (meth) acryloyl groups at the terminal or side chain. 30 to 70 parts by weight of a prepolymer having a molecular weight of 500 to 5000 is added. If the amount of component (a) added is less than 30 parts by mass, the internal stress at the time of curing the adhesive may increase, and if it exceeds 70 parts by mass, sufficient initial adhesive strength may not be obtained. There is sex.
本発明では、成分（ｂ）としてイソボルニルメタクリレートが２０〜６０質量部添加される。成分（ｂ）の添加量が、２０質量部未満であると初期に充分な接着強さが得られない可能性があり、又６０質量部を超えると、内部応力が大きくなる可能性がある。 In the present invention, 20 to 60 parts by mass of isobornyl methacrylate is added as the component (b). If the amount of component (b) added is less than 20 parts by mass, sufficient initial adhesive strength may not be obtained, and if it exceeds 60 parts by mass, internal stress may increase.
本発明では成分（ｃ）として下記化学式で表される（メタ）アクリレートモノマーが１０〜４０質量部、添加される。
具体的には、プロポキシエチル（メタ）アクリレート、ブトキシエチル（メタ）アクリレートがこれにあたる。ｎ＝２以下の化合物では、接着耐久性が低下する可能性がある。ｎ＝４以上の化合物では、初期に充分な接着強さが得られない可能性がある。又、同化合物の添加量が１０質量部未満では接着剤硬化の際に発生する内部応力が大きくなる可能性が高く、６０質量部を超える場合、初期に充分な接着強さが得られない可能性がある。 Specifically, propoxyethyl (meth) acrylate and butoxyethyl (meth) acrylate correspond to this. With a compound of n = 2 or less, the adhesion durability may be lowered. When n = 4 or more, there is a possibility that sufficient adhesive strength cannot be obtained in the initial stage. Also, if the amount of the compound added is less than 10 parts by mass, the internal stress generated during the curing of the adhesive is likely to increase, and if it exceeds 60 parts by mass, sufficient adhesive strength may not be obtained in the initial stage. There is sex.
本発明に用いる成分（ｄ）光重合開始剤は、紫外線や可視光線等の活性光線により増感させて樹脂組成物の光硬化を促進するために配合するものであり、公知の各種光重合開始剤が使用可能である。具体的には、１−ヒドロキシシクロヘキシルフェニルケトン、ベンゾフェノン、ｐ−メトキシベンゾフェノン、アセトフェノン、プロピオフェノン、チオキサントン、２，２−ジメトキシ−２−フェニルアセトフェノン、２，２−ジエトキシ−２−フェニルアセトフェノン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ｐ−クロロベンゾフェノン、４−ベンゾイル−４−メチルジフェニルサルファイド、２−ベンジル−２−ジメチルアミノ−１−（４−モルホリノフェニル）−ブタノン−１、２−メチル−１［４−（メチルチオ）フェニル］−２−モルホリノプロパノン−１等が例示できる。 The component (d) photopolymerization initiator used in the present invention is blended to accelerate photocuring of the resin composition by sensitizing with active light such as ultraviolet rays and visible rays, and various known photopolymerization initiations. The agent can be used. Specifically, 1-hydroxycyclohexyl phenyl ketone, benzophenone, p-methoxybenzophenone, acetophenone, propiophenone, thioxanthone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, benzoin Methyl ether, benzoin ethyl ether, p-chlorobenzophenone, 4-benzoyl-4-methyldiphenyl sulfide, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, 2-methyl-1 [ 4- (methylthio) phenyl] -2-morpholinopropanone-1 and the like can be exemplified.
これら光重合開始剤は、１種もしくは２種以上を組み合わせて使用することができる。重合開始剤の配合量は、成分（ａ）、成分（ｂ）、成分（ｃ）の合計量１００質量部に対して、０．００１〜２０質量部、好ましくは０．１〜１５質量部である。 These photopolymerization initiators can be used alone or in combination of two or more. The compounding quantity of a polymerization initiator is 0.001-20 mass parts with respect to 100 mass parts of total amounts of a component (a), a component (b), and a component (c), Preferably it is 0.1-15 mass parts. is there.
また、本発明の光硬化性樹脂組成物は、必要に応じて、シランカップリング剤や酸性リン酸エステル等の密着性向上剤、貯蔵安定性を向上させる目的で添加させる酸化防止剤、その他、硬化促進剤、染料、充填剤、顔料、チキソトロピー付与剤、可塑剤、界面活性剤、滑剤、帯電防止剤などの添加剤を加えることができる。 In addition, the photocurable resin composition of the present invention, if necessary, an adhesion improver such as a silane coupling agent or acidic phosphate ester, an antioxidant added for the purpose of improving storage stability, Additives such as curing accelerators, dyes, fillers, pigments, thixotropy imparting agents, plasticizers, surfactants, lubricants and antistatic agents can be added.
以下実験例により本発明を説明する。各物質の使用量の単位は質量部で示す。なお、各種物性は、次のように測定した。 Hereinafter, the present invention will be described with reference to experimental examples. The unit of the amount used of each substance is shown in parts by mass. Various physical properties were measured as follows.
〔光硬化条件〕光硬化に際しては、無電極放電ランプを使用したフュージョン社製硬化装置により、３６５ｎｍの波長の積算光量２０００ｍＪ／ｃｍ２の条件にて硬化させた。 [Photo-curing conditions] In photo-curing, curing was performed under a condition of an integrated light quantity of 2000 mJ / cm 2 at a wavelength of 365 nm by a curing apparatus manufactured by Fusion Corporation using an electrodeless discharge lamp.
〔剪断接着強さ〕一枚のアルミ試験片（１００ｍｍ×２５ｍｍ×２．０ｍｍ、Ａ−５０５２材）の片端より約１２ｍｍの部位に、ボール板で直径８ｍｍの穴を空ける。８ｍｍの穴の片面を覆うように、ガラス試験片（２５ｍｍ×２５ｍｍ×２ｍｍパイレックス耐熱ガラス）を固定し、穴の中に接着剤を塗布し、上記条件にて接着剤を硬化させる。硬化後ガラスの裏面に他のアルミ試験片を市販の常温硬化型接着剤にて接着し試験片とした。引っ張り剪断接着強さ（単位：ＭＰａ）は、温度２３℃、湿度５０％の環境下で引張速度１０ｍｍ／分で測定した。 [Shear bond strength] A hole having a diameter of 8 mm is made with a ball plate at a position about 12 mm from one end of one aluminum test piece (100 mm x 25 mm x 2.0 mm, A-5052 material). A glass test piece (25 mm × 25 mm × 2 mm Pyrex heat-resistant glass) is fixed so as to cover one side of an 8 mm hole, an adhesive is applied in the hole, and the adhesive is cured under the above conditions. After curing, another aluminum test piece was bonded to the back surface of the glass with a commercially available room temperature curing adhesive to obtain a test piece. The tensile shear bond strength (unit: MPa) was measured at a tensile speed of 10 mm / min in an environment of a temperature of 23 ° C. and a humidity of 50%.
〔耐湿性評価〕剪断接着強さ評価と同様な試験片を作製後、プレッシャークッカー試験装置（１２１℃×１００％ＲＨ）中にて４８時間放置し、取り出し後、２３℃×５０％ＲＨ雰囲気の室内にて３０分以上放置後、接着強さを測定した。 [Moisture Resistance Evaluation] After preparing a test piece similar to the shear bond strength evaluation, the specimen was left in a pressure cooker test apparatus (121 ° C. × 100% RH) for 48 hours, taken out, and then placed in a 23 ° C. × 50% RH atmosphere. After standing in the room for 30 minutes or more, the adhesive strength was measured.
〔硬化時に発生する内部応力評価方法〕接着剤硬化時に発生する内部応力は、下記評価方法により測定、評価を実施した。２００ｍｍ×２５ｍｍ×０．３ｍｍのＳＰＣＣ−ＳＢ試験片上に、１００ｍｍ×１０ｍｍ×１ｍｍの形状に切り抜いたシリコンシート型枠を圧着し、型枠中に接着剤を注入し、ＰＥＴフィルムで上部を覆う。接着剤硬化前の試験片の状態を図１に示す。この試験片を上記紫外線硬化条件にて接着剤硬化後に、型枠を取り外し、ＳＰＣＣ試験片の反りにより生ずる変位を測定し評価に用いた。接着剤硬化後の試験片の状態を図２に示す。 [Method for evaluating internal stress generated during curing] The internal stress generated during curing of the adhesive was measured and evaluated by the following evaluation method. A silicon sheet mold cut out to a shape of 100 mm × 10 mm × 1 mm is pressure-bonded onto a 200 mm × 25 mm × 0.3 mm SPCC-SB test piece, an adhesive is injected into the mold, and the upper part is covered with a PET film. The state of the test piece before adhesive curing is shown in FIG. After the test piece was cured with the adhesive under the above UV curing conditions, the mold was removed and the displacement caused by the warp of the SPCC test piece was measured and used for evaluation. The state of the test piece after adhesive curing is shown in FIG.
〔総合評価〕総合評価として、初期接着強さが１０ＭＰa以上であり、且つ接着耐久性評価が、初期接着性の９０％を超えており、且つ硬化時の内部応力評価値が１．０ｍｍ未満である例を○とし、それ以外の評価を×とした。 [Comprehensive evaluation] As a comprehensive evaluation, the initial adhesive strength is 10 MPa or more, the adhesive durability evaluation exceeds 90% of the initial adhesiveness, and the internal stress evaluation value at the time of curing is less than 1.0 mm. A certain example was set as ◯, and other evaluations were set as ×.
（実験例１）表１の使用量で各物質を混合して光硬化性組成物を調製した。これについて、剪断接着強さ、接着耐久性評価、硬化時に発生する内部応力を評価した。結果を表１に併記した。
また、配合組成中の成分ａとしては、
ａ−１：末端アクリル変性ポリブタジエン（日本曹達（社）製商品名ＴＥ−２０００）
ａ−２：末端アクリル変性ポリブタジエン水素添加品（日本曹達（社）製）を用い、分子内の主鎖骨格がポリブタジエン、ポリイソプレン又はその水素添加物でない両端又は側鎖に１個以上の（メタ）アクリロイル基を有する、分子量５００から５０００のプレポリマーの例として、東亜合成（株）社製アロニックスＭ−１６００を使用した。更に、シランカップリング剤には、日本ユニカ（株）社製Ａ−１７４を使用した。
In addition, as component a in the composition,
a-1: Terminal acrylic modified polybutadiene (Nippon Soda Co., Ltd., trade name TE-2000)
a-2: A terminal acryl-modified polybutadiene hydrogenated product (manufactured by Nippon Soda Co., Ltd.), and the main chain skeleton in the molecule is one or more (meta) at both ends or side chains that are not polybutadiene, polyisoprene or its hydrogenated product ) Aronix M-1600 manufactured by Toa Gosei Co., Ltd. was used as an example of a prepolymer having an acryloyl group and a molecular weight of 500 to 5000. Furthermore, Nippon Unica Co., Ltd. A-174 was used for the silane coupling agent.
（実験例２）表２の使用量で各物質を混合して光硬化性接着剤組成物を調製したこと以外は、実験例１と同様に行った。結果を表２に併記した。
本発明の光硬化性樹脂組成物により初期に高い接着強さを有し、高湿度下での強度低下が極めて小さく、且つ接着剤硬化時に発生する内部応力の小さい接着剤が得られるため、接着剤の内部応力が影響する、プラスチック製光学材料のへの接着の適用が可能となる。 The photo-curable resin composition of the present invention has an initial high adhesive strength, an extremely low decrease in strength under high humidity, and an adhesive having a low internal stress generated when the adhesive is cured. It is possible to apply an adhesive to a plastic optical material affected by the internal stress of the agent.
１ 接着剤
２ シリコン型枠
３ ＰＥＴフィルム
４ 冷間圧延鋼板（ＳＰＣＣ）
DESCRIPTION OF SYMBOLS 1 Adhesive 2
Claims (1)
（ｃ）下記化学式で表される（メタ）アクリレートモノマー１０〜４０質量部、
および（ｄ）光重合開始剤を含有することを特徴とする光硬化性樹脂組成物。
(C) 10 to 40 parts by mass of a (meth) acrylate monomer represented by the following chemical formula,
And (d) a photopolymerization initiator, and a photocurable resin composition.
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