JPH0670209B2 - Optical adhesive - Google Patents
Optical adhesiveInfo
- Publication number
- JPH0670209B2 JPH0670209B2 JP29559289A JP29559289A JPH0670209B2 JP H0670209 B2 JPH0670209 B2 JP H0670209B2 JP 29559289 A JP29559289 A JP 29559289A JP 29559289 A JP29559289 A JP 29559289A JP H0670209 B2 JPH0670209 B2 JP H0670209B2
- Authority
- JP
- Japan
- Prior art keywords
- adhesive
- vinylcarbazole
- refractive index
- weight
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000001070 adhesive effect Effects 0.000 title claims description 54
- 239000000853 adhesive Substances 0.000 title claims description 53
- 230000003287 optical effect Effects 0.000 title description 17
- 229940126062 Compound A Drugs 0.000 claims description 11
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 7
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 claims description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- 239000003505 polymerization initiator Substances 0.000 claims description 4
- UBPXWZDJZFZKGH-UHFFFAOYSA-N 1-ethenyl-3-methylpyrrolidin-2-one Chemical group CC1CCN(C=C)C1=O UBPXWZDJZFZKGH-UHFFFAOYSA-N 0.000 claims description 3
- FNALUOMDZYDJLK-UHFFFAOYSA-N 9-ethenyl-3-nitrocarbazole Chemical group C1=CC=C2C3=CC([N+](=O)[O-])=CC=C3N(C=C)C2=C1 FNALUOMDZYDJLK-UHFFFAOYSA-N 0.000 claims description 3
- RKHBMAZBULNFTM-UHFFFAOYSA-N 9-ethenylcarbazol-3-amine Chemical compound C1=CC=C2C3=CC(N)=CC=C3N(C=C)C2=C1 RKHBMAZBULNFTM-UHFFFAOYSA-N 0.000 claims description 3
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 3
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 3
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical group CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 claims description 3
- HQGPZXPTJWUDQR-UHFFFAOYSA-N 1-ethenyl-5-methylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1C=C HQGPZXPTJWUDQR-UHFFFAOYSA-N 0.000 claims description 2
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 claims description 2
- ORMIJZCMQBMNFA-UHFFFAOYSA-N 3,6-dibromo-9-ethenylcarbazole Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3N(C=C)C2=C1 ORMIJZCMQBMNFA-UHFFFAOYSA-N 0.000 claims description 2
- BJPRMONRDLJVCD-UHFFFAOYSA-N 3-benzyl-1-ethenylpyrrolidin-2-one Chemical compound O=C1N(C=C)CCC1CC1=CC=CC=C1 BJPRMONRDLJVCD-UHFFFAOYSA-N 0.000 claims description 2
- BCFAZFGWDQRUTC-UHFFFAOYSA-N 9-ethenyl-1,2,3,4-tetrahydrocarbazole Chemical compound C12=CC=CC=C2N(C=C)C2=C1CCCC2 BCFAZFGWDQRUTC-UHFFFAOYSA-N 0.000 claims description 2
- RQEBVYHEWZWMSJ-UHFFFAOYSA-N 9-ethenyl-n-methylcarbazol-3-amine Chemical compound C1=CC=C2C3=CC(NC)=CC=C3N(C=C)C2=C1 RQEBVYHEWZWMSJ-UHFFFAOYSA-N 0.000 claims description 2
- DFENKTCEEGOWLB-UHFFFAOYSA-N n,n-bis(methylamino)-2-methylidenepentanamide Chemical compound CCCC(=C)C(=O)N(NC)NC DFENKTCEEGOWLB-UHFFFAOYSA-N 0.000 claims description 2
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 claims description 2
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 claims description 2
- CNPHCSFIDKZQAK-UHFFFAOYSA-N n-prop-2-enylprop-2-enamide Chemical compound C=CCNC(=O)C=C CNPHCSFIDKZQAK-UHFFFAOYSA-N 0.000 claims description 2
- UIHSTNXWLQMGGF-UHFFFAOYSA-N 3,3,5-trimethylpyrrolidin-2-one Chemical group CC1CC(C)(C)C(=O)N1 UIHSTNXWLQMGGF-UHFFFAOYSA-N 0.000 claims 1
- YRVUCYWJQFRCOB-UHFFFAOYSA-N n-butylprop-2-enamide Chemical group CCCCNC(=O)C=C YRVUCYWJQFRCOB-UHFFFAOYSA-N 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 239000005304 optical glass Substances 0.000 description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 239000012790 adhesive layer Substances 0.000 description 4
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 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 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 2
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 2
- IUDWGHRBQRGLDJ-UHFFFAOYSA-N 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-4-carboxylic acid Chemical compound C1CC2(C(O)=O)C(=O)C(=O)C1C2(C)C IUDWGHRBQRGLDJ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229930006711 bornane-2,3-dione Natural products 0.000 description 2
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- NAGSMIOYEJTYQT-UHFFFAOYSA-N 1-ethenyl-3,3,5-trimethylpyrrolidin-2-one Chemical compound CC1CC(C)(C)C(=O)N1C=C NAGSMIOYEJTYQT-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 1
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 244000283070 Abies balsamea Species 0.000 description 1
- 239000004858 Canada balsam Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- -1 acrylic ester Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 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
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は光学部品等の接着に用いられる透明な接着剤に
関するものであり、更に詳しくは硬化後の屈折率が極め
て高い光学用接着剤に関するものである。Description: TECHNICAL FIELD The present invention relates to a transparent adhesive used for bonding optical parts and the like, and more particularly to an optical adhesive having an extremely high refractive index after curing. It is a thing.
［従来の技術］ 従来、光学部品の接着にはカナダバルサムやアクリル
系、エポキシ系の接着剤が主に用いられてきた。[Prior Art] Conventionally, adhesives of Canada balsam, acrylic, or epoxy have been mainly used for bonding optical components.
また近年、光ファイバーの接合などにおいて光学部品と
接着剤との界面での屈折率の差による光の反射によるロ
スを防止するため、接着剤の屈折率を接着する光学部品
の屈折率と一致させた接着剤が開発されてきている。Further, in recent years, in order to prevent the loss due to the reflection of light due to the difference in the refractive index at the interface between the optical component and the adhesive when joining optical fibers, the refractive index of the adhesive is made to match the refractive index of the optical component to be bonded. Adhesives have been developed.
このような接着剤としては、例えばグリセロール変性ビ
スフェノールＡジ（メタ）アクリレートとグリセロール
変性フッ素含有ビスフェノールＡジ（メタ）アクリレー
トとを必須成分とする接着剤があり、該接着剤組成物中
のフッ素含有量を調節することによって1.45から1.59の
範囲で屈折率（nd）を調整できるものが上市されている
（Polymer Preprints,Japan vol.38,No.5（1989）,p128
4,p1304）。Examples of such an adhesive include an adhesive containing glycerol-modified bisphenol A di (meth) acrylate and glycerol-modified fluorine-containing bisphenol A di (meth) acrylate as essential components. It is marketed that the refractive index (n d ) can be adjusted in the range of 1.45 to 1.59 by adjusting the amount (Polymer Preprints, Japan vol.38, No.5 (1989), p128.
4, p1304).
［発明が解決しようとする課題］ しかしながら、光導波路の設計や多数枚の光学レンズを
組合わせた光学系の設計などにおいては屈折率（nd）が
1.60以上を有する光学材料や光学素子を使用したいとい
う要求がある。このような光学部品の接合においては、
従来の接着剤は屈折率が低いため、前述のごとく光学部
品と接着剤との屈折率差に起因する接合ロスを生じると
いう問題があった。[Problems to be Solved by the Invention] However, in the design of an optical waveguide or the design of an optical system in which a large number of optical lenses are combined, the refractive index (n d ) is
There is a demand to use optical materials and optical elements having 1.60 or higher. In joining such optical components,
Since the conventional adhesive has a low refractive index, there has been a problem that a bonding loss occurs due to the difference in the refractive index between the optical component and the adhesive as described above.
本発明は、かかる従来技術における問題点を解決すべ
く、高屈折率を有する優れた光学用接着剤を提供するこ
とを目的とするものである。SUMMARY OF THE INVENTION It is an object of the present invention to provide an excellent optical adhesive having a high refractive index in order to solve the problems in the conventional art.
［課題を解決するための手段］ 即ち、本発明は、Ｎ−ビニルカルバゾール及びその置換
体から成る群より選ばれた少なくとも一種の化合物Ａ
と、Ｎ−ビニルピロリドン及びその置換体並びにアクリ
ルアミドＮ置換体から成る群より選ばれた少なくとも一
種の化合物Ｂを含み、硬化後の屈折率（nd）が1.60以上
であることを特徴とする接着剤に係るものである。[Means for Solving the Problems] That is, the present invention provides at least one compound A selected from the group consisting of N-vinylcarbazole and its substituted compounds.
If, comprising at least one compound B selected from the group consisting of N- vinylpyrrolidone and derivatives thereof and acrylamide N-substituted body, the refractive index after curing (n d) is characterized in that 1.60 or more adhesive It is related to the agent.
本発明の化合物Ａは、重合性及び高屈折率性を有する物
質であって、室温では結晶性固体である。The compound A of the present invention is a substance having polymerizability and high refractive index, and is a crystalline solid at room temperature.
本発明の化合物Ｂは、化合物Ａと同様に重合性を有する
とともに、親水性であるためにガラス等の光学部材に対
する接着性が高い。更に、化合物Ａを高濃度に溶解せし
め、それとの共重合性にも優れているために、重合硬化
後には極めて透明度の高い状態を呈することのできる物
質である。Like the compound A, the compound B of the present invention has polymerizability and is hydrophilic, so that it has high adhesiveness to an optical member such as glass. Furthermore, since compound A is dissolved in a high concentration and has excellent copolymerizability with it, it is a substance capable of exhibiting an extremely high transparency after polymerization and curing.
従って、本発明の化合物ＡとＢを組合せることにより、
高屈折率を有し透明性に優れた接着剤を得ることができ
る。Therefore, by combining the compounds A and B of the present invention,
An adhesive having a high refractive index and excellent transparency can be obtained.
尚、接着強度及び接着耐水性等の他の接着剤としての特
性についても、本発明の接着剤は従来のものに劣らない
性質を有している。The adhesive of the present invention has properties comparable to those of conventional adhesives in terms of other adhesive properties such as adhesive strength and adhesive water resistance.
Ｎ−ビニルカルバゾール置換体の好適具体例としては、
３−ニトロ−Ｎ−ビニルカルバゾール、３−アミノ−Ｎ
−ビニルカルバゾール、３−メチルアミノ−Ｎ−ビニル
カルバゾール、1,2,3,4−テトラヒドロ−Ｎ−ビニルカ
ルバゾール及び3,6−ジブロム−Ｎ−ビニルカルバゾー
ルがあり、Ｎ−ビニルピロリドン置換体の好適具体例と
しては、Ｎ−ビニル−３−メチルピロリドン、Ｎ−ビニ
ル−５−メチルピロリドン、Ｎ−ビニル−３−ベンジル
ピロリドン及びＮ−ビニル−3,3,5−トリメチルピロリ
ドンがあり、及びアクリルアミドＮ置換体の好適具体例
としては、Ｎ−メチルアクリルアミド、Ｎ−エチルアク
リルアミド、Ｎ−ｎ−プロピルアクリルアミド、Ｎ−ｎ
−ブチルアクリルアミド、Ｎ−アリルアクリルアミド、
N,N−ジメチルアクリルアミド、N,N−ジエチルアクリル
アミド、N,N−ジメチルアミノプロピルアクリルアミド
及びアクリロイルモルホリンを挙げることができる。Specific preferred examples of the N-vinylcarbazole-substituted product include:
3-nitro-N-vinylcarbazole, 3-amino-N
-Vinylcarbazole, 3-methylamino-N-vinylcarbazole, 1,2,3,4-tetrahydro-N-vinylcarbazole and 3,6-dibromo-N-vinylcarbazole, and preferred N-vinylpyrrolidone substituted compounds Specific examples include N-vinyl-3-methylpyrrolidone, N-vinyl-5-methylpyrrolidone, N-vinyl-3-benzylpyrrolidone and N-vinyl-3,3,5-trimethylpyrrolidone, and acrylamide N Preferable specific examples of the substituent include N-methyl acrylamide, N-ethyl acrylamide, Nn-propyl acrylamide and N-n.
-Butyl acrylamide, N-allyl acrylamide,
Mention may be made of N, N-dimethylacrylamide, N, N-diethylacrylamide, N, N-dimethylaminopropylacrylamide and acryloylmorpholine.
本発明接着剤を硬化する方法としては、高温加熱や電子
線、放射線の照射がある。更に、本発明接着剤に通常用
いられる重合開始剤を添加し、紫外光又は可視光等の照
射を行なったり、加熱する等の手段を用いて硬化するこ
とができる。As a method for curing the adhesive of the present invention, heating at high temperature, irradiation with an electron beam, or irradiation with radiation is used. Further, a polymerization initiator usually used in the adhesive of the present invention can be added, and the adhesive can be cured by irradiation with ultraviolet light or visible light or by heating.
かかる重合開始剤としては、ベンゾイルパーオキサイド
（BPO）及びアゾビスイソブチロニトリル（AIBN）のよ
うな通常の熱重合型開始剤、又はベンゾフェノン、ベン
ゾインエーテル、チオキサンゾン、ベンジル、１−ヒド
ロキシシクロヘキシルフェニルケトン、ヒドロキシアセ
トフェノン、１−カルボキシ−7,7−ジメチルビシクロ
［2,2,1］ヘプタン−2,3−ジオン及びカンファ−キノン
等の通常の光重合型開始剤を使用することができる。Examples of such a polymerization initiator include usual thermal polymerization type initiators such as benzoyl peroxide (BPO) and azobisisobutyronitrile (AIBN), or benzophenone, benzoin ether, thioxanthone, benzyl, 1-hydroxycyclohexyl phenyl ketone. Conventional photopolymerization initiators such as, hydroxyacetophenone, 1-carboxy-7,7-dimethylbicyclo [2,2,1] heptane-2,3-dione and camphorquinone can be used.
光重合型開始剤を使用する場合には、N,N−ジメチル−
ｐ−トルイジン等の第三級アミンを添加することにより
硬化速度を著しく増大させることができる。When using a photopolymerization initiator, N, N-dimethyl-
The curing rate can be significantly increased by adding a tertiary amine such as p-toluidine.
更に、第三級アミンと前記有機過酸化物を組合せたレド
ックス系を重合開始剤として用いることも可能である。Further, a redox system in which a tertiary amine and the above organic peroxide are combined can be used as a polymerization initiator.
本発明接着剤中の各成分の組成割合は硬化後の屈折率が
1.60以上となるように、種々の目的及び用途に応じて、
当業者が適宜決めることができる。従って、化合物Ａ及
びＢの組成割合を変化させることによって、本発明接着
剤の屈折率を調整することが可能である。The composition ratio of each component in the adhesive of the present invention is such that the refractive index after curing is
Depending on various purposes and uses, it will be 1.60 or more.
It can be appropriately determined by those skilled in the art. Therefore, the refractive index of the adhesive of the present invention can be adjusted by changing the composition ratio of the compounds A and B.
化合物Ａの組成割合が30重量％未満となると、得られる
接着剤の硬化後の屈折率（nd）が1.60未満となってしま
う場合があるため、好ましくない。また、接着剤として
の所望の接着力を得るためには、化合物Ｂが少なくとも
約２重量％含まれていることが好ましい。When the composition ratio of the compound A is less than 30% by weight, the refractive index (n d ) of the obtained adhesive after curing may be less than 1.60, which is not preferable. Further, in order to obtain a desired adhesive strength as an adhesive, it is preferable that the compound B is contained in an amount of at least about 2% by weight.
更に、化合物Ａの組成割合が65重量％以下の場合には、
室温において接着剤が液体状となるため扱い易く操作性
に優れたものが得られる。Furthermore, when the composition ratio of the compound A is 65% by weight or less,
Since the adhesive becomes liquid at room temperature, it is easy to handle and excellent in operability.
また、本発明接着剤に、通常用いられる熱重合禁止剤や
紫外線吸収剤等の添加剤を適宜使用できることはもちろ
んである。さらに、本発明の接着剤を使用するにあたっ
ては、接着強度をより向上させる目的で光学部材に酸、
アルカリ処理、プラズマ処理及びシラン処理等の表面処
理をほどこすことができる。In addition, it goes without saying that additives such as thermal polymerization inhibitors and ultraviolet absorbers that are commonly used can be appropriately used in the adhesive of the present invention. Furthermore, in using the adhesive of the present invention, an acid is added to the optical member for the purpose of further improving the adhesive strength,
Surface treatment such as alkali treatment, plasma treatment and silane treatment can be performed.
尚、屈折率（nd）はナトリウムのＤ線（波長589nm）を
用いて測定した場合の屈折率を示すものである。The refractive index (n d ) is the refractive index when measured using the D line of sodium (wavelength 589 nm).
以下実施例に基づき、本発明を詳説する。Hereinafter, the present invention will be described in detail based on examples.
［実施例１］ Ｎ−ビニルカルバゾール60重量部、Ｎ−ビニルピロリド
ン40重量部及びAIBN 1重量部を調合して攪拌し、室温で
透明な液状の本発明接着剤を得た。この屈折率（nd）は
1.62であった。この接着剤を光学ガラス（Bk-7ガラス）
間に薄く塗布し、70℃の恒温槽中で30分間加熱した。光
学ガラスは強固に接着しており、接着硬化層は白濁がな
く良好な透明性を示した。また、硬化後の屈折率（nd）
は1.64であり極めて高い屈折率を示した。Example 1 60 parts by weight of N-vinylcarbazole, 40 parts by weight of N-vinylpyrrolidone and 1 part by weight of AIBN were mixed and stirred to obtain a transparent liquid adhesive of the present invention at room temperature. This refractive index (n d ) is
It was 1.62. Use this adhesive for optical glass (Bk-7 glass)
A thin coat was applied between them, and the mixture was heated in a constant temperature bath at 70 ° C for 30 minutes. The optical glass was firmly adhered, and the cured adhesive layer did not show cloudiness and showed good transparency. Also, the refractive index (n d ) after curing
Was 1.64, indicating an extremely high refractive index.
［実施例２］ Ｎ−ビニルカルバゾール60重量部、N,N−ジメチルアク
リルアミド40重量部及び１−ヒドロキシシクロヘキシル
フェニルケトン３重量部を調合して攪拌し、室温で透明
な液状の本発明接着剤を得た。この屈折率（nd）は1.59
であった。実施例１と同様に光学ガラス間にこの接着剤
を薄く塗布した後、高圧水銀灯により10mw/cm2の強度の
紫外線を１分間照射した。光学ガラスは強固に接着して
おり、接着硬化層は白濁がなく良好な透明性を示した。
また、硬化後の屈折率（nd）は1.62であり極めて高い屈
折率を示した。Example 2 60 parts by weight of N-vinylcarbazole, 40 parts by weight of N, N-dimethylacrylamide and 3 parts by weight of 1-hydroxycyclohexylphenylketone were mixed and stirred to obtain a transparent liquid adhesive of the present invention at room temperature. Obtained. This refractive index (n d ) is 1.59
Met. This adhesive was thinly applied between optical glasses in the same manner as in Example 1, and then ultraviolet rays having an intensity of 10 mw / cm 2 were irradiated for 1 minute by a high pressure mercury lamp. The optical glass was firmly adhered, and the cured adhesive layer did not show cloudiness and showed good transparency.
The refractive index (n d ) after curing was 1.62, which was an extremely high refractive index.
［実施例３］ ３−アミノ−Ｎ−ビニルカルバゾール35重量部、Ｎ−ビ
ニルピロリドン65重量部、１−カルボキシ−7,7−ジメ
チルビシクロ［2,2,1］ヘプタン−2,3−ジオン0.1重量
部及びN,N−ジメチルパラトルイジン0.1重量部よりなる
本発明接着剤を調合し、実施例１と同様に光学ガラス間
に塗布した後、ハロゲンランプを用いて600キロルック
スの可視光を５分間照射して接着硬化させた。本接着剤
は接着性、透明性に優れており、また、硬化後の屈折率
（nd）は1.60であった。Example 3 35 parts by weight of 3-amino-N-vinylcarbazole, 65 parts by weight of N-vinylpyrrolidone, 1-carboxy-7,7-dimethylbicyclo [2,2,1] heptane-2,3-dione 0.1 An adhesive of the present invention consisting of 1 part by weight and 0.1 part by weight of N, N-dimethylparatoluidine was prepared and applied between optical glasses in the same manner as in Example 1, and then a halogen lamp was used to apply visible light of 600 kilolux to 5 parts. It was irradiated for minutes to cure the adhesive. This adhesive had excellent adhesiveness and transparency, and the refractive index (n d ) after curing was 1.60.
［実施例４］ ３−ニトロ−Ｎ−ビニルカルバゾール55重量部、Ｎ−メ
チルアクリルアミド45重量部、カンファーキノン0.1重
量部及びN,N−ジメチルパラトルイジン0.1重量部を調合
し実施例３と同様に光学ガラスの接着を行なった。接着
性、透明性は良好であり、接着硬化後の屈折率（nd）は
1.61であった。[Example 4] 55 parts by weight of 3-nitro-N-vinylcarbazole, 45 parts by weight of N-methylacrylamide, 0.1 part by weight of camphorquinone and 0.1 part by weight of N, N-dimethylparatoluidine were prepared in the same manner as in Example 3. Adhesion of optical glass was performed. Adhesiveness and transparency are good, and the refractive index (n d ) after adhesive curing is
It was 1.61.
［実施例５］ Ｎ−ビニルカルバゾール60重量部、Ｎ−ビニル−３−メ
チルピロリドン40重量部及びBPO 1重量部を調合して攪
拌し、室温で透明な液状の本発明接着剤を得た。この接
着剤を光学ガラス（Bk-7ガラス）間に薄く塗布し、70℃
の恒温槽中で30分間加熱した。光学ガラスは強固に接着
しており、接着硬化層は白濁がなく良好な透明性を示し
た。また、硬化後の屈折率（nd）は1.63であり極めて高
い屈折率を示した。Example 5 60 parts by weight of N-vinylcarbazole, 40 parts by weight of N-vinyl-3-methylpyrrolidone and 1 part by weight of BPO were mixed and stirred to obtain a transparent liquid adhesive of the present invention at room temperature. Apply this adhesive thinly between optical glass (Bk-7 glass),
It was heated for 30 minutes in the constant temperature bath. The optical glass was firmly adhered, and the cured adhesive layer did not show cloudiness and showed good transparency. The refractive index (n d ) after curing was 1.63, which was an extremely high refractive index.
次に、本発明の比較例として、本発明化合物Ｂの代り
に、通常のアクリル系接着剤として用いられる、２−ヒ
ドロキシエチル（メタ）アクリレート及びビスフェノー
ルＡグリセロール変性ジ（メタ）アクリレート等の（メ
タ）アクリル酸エステル又はパラクロロスチレンを用い
て接着剤を調製した。Next, as a comparative example of the present invention, in place of the compound B of the present invention, 2-hydroxyethyl (meth) acrylate and bisphenol A glycerol-modified di (meth) acrylate, which are used as ordinary acrylic adhesives, (meta) are used. ) Adhesives were prepared with acrylic ester or parachlorostyrene.
［比較例１］ Ｎ−ビニルピロリドンを用いるかわりに、２−ヒドロキ
シエチルメタクリレートを用いた以外は実施例１と同様
の組成とした。Ｎ−ビニルカルバゾールが均一に溶解せ
ず光学用接着剤として使用できなかった。[Comparative Example 1] The same composition as in Example 1 was used except that 2-hydroxyethyl methacrylate was used instead of using N-vinylpyrrolidone. N-vinylcarbazole did not dissolve uniformly and could not be used as an optical adhesive.
［比較例２］ Ｎ−ビニルカルバゾール50重量部、パラクロロスチレン
50重量部及びAIBN0.05重量部を調合し、室温で透明な液
状組成物を得た。この組成物の屈折率（nd）は1.62であ
った。65℃で３時間加熱し、光学ガラスの接着を行なっ
たところ接着層が白濁してしまった。[Comparative Example 2] 50 parts by weight of N-vinylcarbazole, parachlorostyrene
50 parts by weight and 0.05 part by weight of AIBN were mixed to obtain a transparent liquid composition at room temperature. The refractive index (n d ) of this composition was 1.62. When the optical glass was bonded by heating at 65 ° C. for 3 hours, the adhesive layer became cloudy.
［比較例３］ ビスフェノールＡグリセロール変性ジアクリレート100
重量部１−ヒドロキシシクロヘキシルフェニルケトン３
重量部を調合し実施例２と同様に接着した。接着硬化物
の屈折率（nd）は1.58であった。[Comparative Example 3] Bisphenol A glycerol modified diacrylate 100
Parts by weight 1-hydroxycyclohexyl phenyl ketone 3
Parts by weight were mixed and bonded in the same manner as in Example 2. The refractive index (n d ) of the adhesive cured product was 1.58.
［発明の効果］ 以上、実施例で得られた結果から明らかなように本発明
の接着剤は高い屈折率、良好な接着性、及び優れた透明
性を兼ね備えている。また、上記比較例の結果から明ら
かなように、本発明化合物Ｂを使用しない場合には、化
合物Ａが充分溶解できずに接着剤が白濁してしまった
り、またたとえ均一に溶解したとしても、化合物Ａとの
共重合性が悪いため、接着硬化後に白濁してしまった
り、所望の屈折率が得られなかったりして本発明が目的
とする優れた接着剤を得ることができなかった。[Effects of the Invention] As is clear from the results obtained in the above examples, the adhesive of the present invention has a high refractive index, good adhesiveness, and excellent transparency. Further, as is clear from the results of the above Comparative Examples, when the compound B of the present invention is not used, the compound A cannot be sufficiently dissolved and the adhesive becomes cloudy, or even if it is uniformly dissolved, Since the copolymerizability with the compound A was poor, it became cloudy after the adhesive was cured, and the desired refractive index was not obtained, so that the excellent adhesive intended by the present invention could not be obtained.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｇ０２Ｂ 1/04 8807−2Ｋ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI technical display location G02B 1/04 8807-2K
Claims (5)
ら成る群より選ばれた少なくとも一種の化合物Ａと、Ｎ
−ビニルピロリドン及びその置換体並びにアクリルアミ
ドＮ置換体から成る群より選ばれた少なくとも一種の化
合物Ｂを含み、硬化後の屈折率（nd）が1.60以上である
ことを特徴とする接着剤。1. At least one compound A selected from the group consisting of N-vinylcarbazole and substituted compounds thereof, and N.
An adhesive characterized by containing at least one compound B selected from the group consisting of vinylpyrrolidone and its substituted product and acrylamide N-substituted product, and having a refractive index (n d ) after curing of 1.60 or more.
ロ−Ｎ−ビニルカルバゾール、３−アミノ−Ｎ−ビニル
カルバゾール、３−メチルアミノ−Ｎ−ビニルカルバゾ
ール、1,2,3,4−テトラヒドロ−Ｎ−ビニルカルバゾー
ル又は3,6−ジブロム−Ｎ−ビニルカルバゾールであ
り、Ｎ−ビニルピロリドン置換体がＮ−ビニル−３−メ
チルピロリドン、Ｎ−ビニル−５−メチルピロリドン、
Ｎ−ビニル−３−ベンジルピロリドン又はＮ−ビニル−
3,3,5−トリメチルピロリドンであり、アクリルアミド
Ｎ置換体が、Ｎ−メチルアクリルアミド、Ｎ−エチルア
クリルアミド、Ｎ−ｎ−プロピルアクリルアミド、Ｎ−
ｎ−ブチルアクリルアミド、Ｎ−アリルアクリルアミ
ド、N,N−ジメチルアクリルアミド、N,N−ジエチルアク
リルアミド、N,N−ジメチルアミノプロピルアクリルア
ミド又はアクリロイルモルホリンであることを特徴とす
る、請求項１記載の接着剤。2. An N-vinylcarbazole-substituted product is 3-nitro-N-vinylcarbazole, 3-amino-N-vinylcarbazole, 3-methylamino-N-vinylcarbazole, 1,2,3,4-tetrahydro- N-vinylcarbazole or 3,6-dibromo-N-vinylcarbazole, wherein the N-vinylpyrrolidone substitution product is N-vinyl-3-methylpyrrolidone, N-vinyl-5-methylpyrrolidone,
N-vinyl-3-benzylpyrrolidone or N-vinyl-
It is 3,3,5-trimethylpyrrolidone, and the acrylamide N-substituted product is N-methylacrylamide, N-ethylacrylamide, Nn-propylacrylamide, N-
Adhesive according to claim 1, characterized in that it is n-butylacrylamide, N-allylacrylamide, N, N-dimethylacrylamide, N, N-diethylacrylamide, N, N-dimethylaminopropylacrylamide or acryloylmorpholine. .
する請求項１又は２記載の接着剤。3. The adhesive according to claim 1, further comprising a polymerization initiator.
とを特徴とする請求項１〜３のいずれか一項記載の接着
剤。4. The adhesive according to claim 1, wherein the compound A is contained in an amount of 30 to 97% by weight.
とを特徴とする請求項４記載の接着剤。5. The adhesive according to claim 4, wherein the compound A is contained in an amount of 30 to 65% by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29559289A JPH0670209B2 (en) | 1989-11-14 | 1989-11-14 | Optical adhesive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29559289A JPH0670209B2 (en) | 1989-11-14 | 1989-11-14 | Optical adhesive |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03157471A JPH03157471A (en) | 1991-07-05 |
| JPH0670209B2 true JPH0670209B2 (en) | 1994-09-07 |
Family
ID=17822625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29559289A Expired - Lifetime JPH0670209B2 (en) | 1989-11-14 | 1989-11-14 | Optical adhesive |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0670209B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101910348B (en) * | 2007-10-30 | 2013-07-03 | 3M创新有限公司 | High refractive index adhesives |
| KR101635722B1 (en) * | 2013-09-05 | 2016-07-01 | 주식회사 다이셀 | Resin composition and cured article thereof |
| JP7126479B2 (en) * | 2019-07-23 | 2022-08-26 | 日東電工株式会社 | Polarizing plate with retardation layer and organic EL display device |
-
1989
- 1989-11-14 JP JP29559289A patent/JPH0670209B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03157471A (en) | 1991-07-05 |
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