JPH01118802A - Optical resin - Google Patents
Optical resinInfo
- Publication number
- JPH01118802A JPH01118802A JP27566787A JP27566787A JPH01118802A JP H01118802 A JPH01118802 A JP H01118802A JP 27566787 A JP27566787 A JP 27566787A JP 27566787 A JP27566787 A JP 27566787A JP H01118802 A JPH01118802 A JP H01118802A
- Authority
- JP
- Japan
- Prior art keywords
- monomers
- refractive index
- kinds
- naphthalene
- vinylbenzyl
- 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.)
- Pending
Links
- 239000011347 resin Substances 0.000 title claims abstract description 17
- 229920005989 resin Polymers 0.000 title claims abstract description 17
- 230000003287 optical effect Effects 0.000 title description 11
- 239000000178 monomer Substances 0.000 claims abstract description 25
- 239000000126 substance Substances 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000004040 coloring Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 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 6
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- -1 diallyl phthalates Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Chemical group 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 239000004641 Diallyl-phthalate Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 2
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 2
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 2
- KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- KXYAVSFOJVUIHT-UHFFFAOYSA-N 2-vinylnaphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC=C21 KXYAVSFOJVUIHT-UHFFFAOYSA-N 0.000 description 1
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- QEEXOZILURWGKW-UHFFFAOYSA-N CCCCOC(=O)C(C)(C)OOC(C)(C)C(=O)O Chemical group CCCCOC(=O)C(C)(C)OOC(C)(C)C(=O)O QEEXOZILURWGKW-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical group CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 239000003963 antioxidant agent 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
- SYFOAKAXGNMQAX-UHFFFAOYSA-N bis(prop-2-enyl) carbonate;2-(2-hydroxyethoxy)ethanol Chemical compound OCCOCCO.C=CCOC(=O)OCC=C SYFOAKAXGNMQAX-UHFFFAOYSA-N 0.000 description 1
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N cinnamyl alcohol Chemical compound OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は光学用樹脂に関し、更に詳細には、耐熱性、耐
衝撃性、耐溶剤性に優れ、且つ高屈折率を有する光学用
樹脂に関する。Detailed Description of the Invention <Industrial Application Field> The present invention relates to an optical resin, and more particularly, to an optical resin having excellent heat resistance, impact resistance, and solvent resistance, and a high refractive index. .
〈従来の技術及びその問題点〉
近年、光学分野では、軽量性、易加工性、安全性、ファ
ツション性などが重視され、プラスチック化が急速に進
んでいる。その代表的なものとしては、ポリメチルメタ
クリレート、ポリジエチレングリコールビスアリルカー
ボネート、ポリスチレン、ポリカーボネート等が知られ
ている。<Conventional technology and its problems> In recent years, in the optical field, emphasis has been placed on lightness, ease of processing, safety, fashionability, etc., and the use of plastics is rapidly progressing. Typical examples thereof include polymethyl methacrylate, polydiethylene glycol bisallyl carbonate, polystyrene, and polycarbonate.
しかしながら、例えばポリメチルメタクリレート、ポリ
ジエチレングリコールビスアリルカーボネートでは、屈
折率が１．４９〜１．５０と小さく、また耐熱性も低い
為、光学分野、特にレンズ等の屈折率、軽量性、耐熱性
が要求される場合には、適さないという欠点がある。However, for example, polymethyl methacrylate and polydiethylene glycol bisallyl carbonate have a small refractive index of 1.49 to 1.50 and low heat resistance. The disadvantage is that it is not suitable when required.
また、ポリスチレン、ポリカーボネートでは、屈折率が
１．５８〜１．５９と比較的高いもののやはりレンズ等
の光学分野においては、不充分であり、更に、これらの
樹脂は、熱可塑性である為、耐熱性が低いこと、光学的
歪が起りやすいこと、また耐溶剤性、耐擦傷性に欠ける
ことなどの欠点がある。In addition, although polystyrene and polycarbonate have a relatively high refractive index of 1.58 to 1.59, they are still insufficient in optical fields such as lenses.Furthermore, since these resins are thermoplastic, they have poor heat resistance. It has disadvantages such as low properties, easy optical distortion, and lack of solvent resistance and scratch resistance.
そこで最近では、高屈折率であって、しかもこれら従来
の欠点を改善するために、高屈折率を有する基を含む多
官能モノマーを主成分あるいは改質剤として用いること
が提案されている。具体的には、ジビニルベンゼン、ジ
アリルフタレート類（特開昭５９−８１３１８） 、ビ
スフェノールＡを有するジメタクリレート（特開昭５５
−１３７４７）、ビスフェノールＡを有するジアリルカ
ーボネート（特開昭５６−１６６２１４）等の多官能モ
ノマーを主成分又は共重合成分として用いる例が挙げら
れている。しかしながら、ジビニルベンゼンを使用する
場合には、高屈折率の樹脂が得られるものの耐衝撃性な
ど機械的強度が低下するという欠点が生じる。また、ジ
アリルフタレート、ビスフェノールＡを有するジメタク
リレートおよびジアリルカーボネートを用いる場合も、
それらの硬化樹脂における屈折率が、１．５２〜１．６
０と低いために、高屈折率を必要とするレンズ等の光学
用樹脂には性能的に不充分であるという欠点がある。Recently, it has been proposed to use a polyfunctional monomer containing a group having a high refractive index as a main component or a modifier in order to improve these conventional drawbacks. Specifically, divinylbenzene, diallyl phthalates (JP-A-59-81318), dimethacrylate containing bisphenol A (JP-A-55
-13747) and diallyl carbonate having bisphenol A (Japanese Unexamined Patent Publication No. 56-166214), examples are given in which polyfunctional monomers are used as the main component or copolymerization component. However, when divinylbenzene is used, although a resin with a high refractive index can be obtained, there is a drawback that mechanical strength such as impact resistance is reduced. Also, when using diallyl phthalate, dimethacrylate containing bisphenol A, and diallyl carbonate,
The refractive index of those cured resins is 1.52 to 1.6.
Since the refractive index is as low as 0, it has the disadvantage of being insufficient in terms of performance for optical resins such as lenses that require a high refractive index.
〈発明の目的〉
本発明の目的は、透明性、高屈折率、耐熱性、耐衝撃性
などに優れた光学用樹脂を提供することにある。<Objective of the Invention> An object of the present invention is to provide an optical resin having excellent transparency, high refractive index, heat resistance, impact resistance, etc.
く問題点を解決するための手段〉
本発明によれば、下記一般式（Ｉ）
（式中、ｍ、ｎは各々０〜４の整数であり、ｍ＋ｎが１
〜４を示す）にて表わされる単量体の１種又は２種以上
を重合させるか若しくは、該単量体の１種又は２種以上
とラジカル重合性モノマーとを共重合させてなる光学用
樹脂が提供される。According to the present invention, the following general formula (I) (where m and n are each an integer of 0 to 4, and m+n is 1
- 4)), or copolymerize one or more of the monomers with a radically polymerizable monomer. A resin is provided.
以下本発明について、更に詳細に説明する。The present invention will be explained in more detail below.
本発明に用いる下記一般式（１）
式中ｍ、ｎは、各々０〜４の整数であり、ｍ＋ｎが１〜
４を示す。ｍ＋ｎが５以上の際は、単量体の合成が複雑
となり、収率が低下するばかりでなく、重合時の着色度
及び機械的強度が劣るため使用できない。The following general formula (1) used in the present invention In the formula, m and n are each an integer of 0 to 4, and m+n is 1 to
4 is shown. When m+n is 5 or more, the synthesis of the monomer becomes complicated and the yield not only decreases, but also the degree of coloration and mechanical strength during polymerization are poor, so that it cannot be used.
本発明に用いる前記一般式（１）により表わされる単量
体としては、例えば、ナフタレン−１−カルボン酸（Ｐ
−ビニルベンジル）エステル、ナフタレン−１−カルボ
ン酸（０−ビニルベンジル）エステル、ナフタレン−２
−カルボン酸（Ｐ−ビニルベンジル）エステル、ナフタ
レン−２−カルボン酸（○−ビニルベンジル）エステル
、ナフタレン−１，８−ジカルボン酸ジ（ｐ−ビニルベ
ンジル）エステル、ナフタレン−１，８−ジカルボン酸
ジ（０−ビニルベンジル）エステル、ナフタレン−２，
３−ジカルボン酸ジ（Ｐ−ビニルベンジル）エステル、
ナフタレン−２，３−ジカルボン酸ジ（０−ビニルベン
ジル）エステル、ナフタレン−２，６ジカルボン酸ジ（
Ｐ−ビニルベンジル）エステル、ナフタレン−２，６−
ジカルボン酸ジ（○−ビニルベンジル）エステル、ナフ
タレン−１，４，５，８−テトラカルボン酸テトラ（Ｐ
−ビニルベンジル）エステル、ナフタレン−１，４，５
，８−テトラカルボン酸テトラ（○−ビニルベンジル）
エステル等を挙げることができる。前記単量体の合成法
としては、例えば、クロロメチルスチレンと所定のナフ
タレンカルボン酸、又はナフタレンジカルボン酸等を水
酸化ナトリウム、水酸化カリウム、トリエチルアミン、
ピリジン等の塩基の存在下にて、加熱反応させる方法、
又は所定のナフタレ、ジカルボン酸又はナフタレンジカ
ルボン酸等を塩化チオニル又は塩化リン等を用いて、酸
ハロゲン化し、次いでヒドロキシメチル−スチレンと、
ピリジン又はトリエチルアミン等の第三級アミンの存在
下において、反応させる方法等により１合成することが
できる。Examples of the monomer represented by the general formula (1) used in the present invention include naphthalene-1-carboxylic acid (P
-vinylbenzyl) ester, naphthalene-1-carboxylic acid (0-vinylbenzyl) ester, naphthalene-2
-Carboxylic acid (P-vinylbenzyl) ester, naphthalene-2-carboxylic acid (○-vinylbenzyl) ester, naphthalene-1,8-dicarboxylic acid di(p-vinylbenzyl) ester, naphthalene-1,8-dicarboxylic acid Di(0-vinylbenzyl)ester, naphthalene-2,
3-dicarboxylic acid di(P-vinylbenzyl) ester,
Naphthalene-2,3-dicarboxylic acid di(0-vinylbenzyl) ester, naphthalene-2,6-dicarboxylic acid di(0-vinylbenzyl) ester,
P-vinylbenzyl) ester, naphthalene-2,6-
dicarboxylic acid di(○-vinylbenzyl) ester, naphthalene-1,4,5,8-tetracarboxylic acid tetra(P
-vinylbenzyl) ester, naphthalene-1,4,5
, 8-tetracarboxylic acid tetra(○-vinylbenzyl)
Examples include esters. As a method for synthesizing the monomer, for example, chloromethylstyrene and a predetermined naphthalenecarboxylic acid or naphthalene dicarboxylic acid are mixed with sodium hydroxide, potassium hydroxide, triethylamine,
A heating reaction method in the presence of a base such as pyridine,
Alternatively, a given naphthalene, dicarboxylic acid, naphthalene dicarboxylic acid, etc. is acid halogenated using thionyl chloride or phosphorus chloride, and then with hydroxymethyl-styrene,
1 can be synthesized by a reaction method in the presence of a tertiary amine such as pyridine or triethylamine.
この場合、いずれの方法においても、適宜溶媒、重合禁
止剤等を使用することが好ましい。In this case, in either method, it is preferable to use a solvent, a polymerization inhibitor, etc. as appropriate.
本発明に用いる前記一般式（１）にて示される単量体の
１種又は２種以上と共重合させるラジカル重合性ビニル
モノマーとしては、例えばスチレン、メチル核置換スチ
レン、ハロゲン核置°換スチレン、α−メチルスチレン
、ジビニルベンゼン。Examples of the radically polymerizable vinyl monomer to be copolymerized with one or more monomers represented by the general formula (1) used in the present invention include styrene, methyl nucleus-substituted styrene, and halogen nucleus-substituted styrene. , α-methylstyrene, divinylbenzene.
アルキル（メタ）アクリレート［アクリレートとメタク
リレートを示す］、フェニル（メタ）アクリレート、ベ
ンジル（メタ）アクリレート、安息香酸ビニル、酢酸ビ
ニル、アクリロニトリル、エチレングリコールジ（メタ
）アクリレート、ジエチレングリコールジ（メタ）アク
リレート、ビスフェノールＡジメタクリレート、２，２
−ビス（４−（メタ）アクリロイルオキシエトキシフェ
ニル）プロパン、フリル（メタ）アクリレート。Alkyl (meth)acrylate [indicates acrylate and methacrylate], phenyl (meth)acrylate, benzyl (meth)acrylate, vinyl benzoate, vinyl acetate, acrylonitrile, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, bisphenol A dimethacrylate, 2,2
-bis(4-(meth)acryloyloxyethoxyphenyl)propane, furyl(meth)acrylate.
２−ヒドロキシエチル（メタ）アクリレート、ポリエチ
レングリコール（メタ）アクリレート、１−ビニルナフ
タレン、２−ビニルナフタレン、ジアリルフタレート、
ジエチレングリコールビスアリルカーボネート等の１種
又は２種以上の混合物を挙げることができる。前記ラジ
カル重合性ビニルモノマーの共重合組成比としては、一
般式（Ｉ）にて示される単量体１００重量部に対して１
〜５０００重量部の範囲であることが望ましい。2-hydroxyethyl (meth)acrylate, polyethylene glycol (meth)acrylate, 1-vinylnaphthalene, 2-vinylnaphthalene, diallyl phthalate,
One type or a mixture of two or more types of diethylene glycol bisallyl carbonate can be mentioned. The copolymerization composition ratio of the radically polymerizable vinyl monomer is 1 part by weight per 100 parts by weight of the monomer represented by general formula (I).
It is desirable that the amount is in the range of 5,000 parts by weight.
本発明の光学用樹脂は、前記一般式（１）にて示される
単量体から１種又は２種以上選択し、ラジカル重合させ
るか、若しくは前記一般式（１）にて示される単量体の
１種又は２種以上と前記ラジカル重合性ビニルモノマー
とを共重合させることにより得られる。前記重合又は共
重合方法としては、一般的なラジカル重合法例えば、塊
状重合法、懸濁重合法等により行なうことが可能であり
、特に塊状重合による注型成型法が好ましい。前記重合
又は共重合に用いるラジカル重合開始剤としては、例え
ば、ジイソプロピルペルオキシジカーボネート、ジノル
マルプロピルペルオキシジカーボネ、−ト、ターシャリ
ブチルペルオキシ２−エチルヘキサノエート、ターシャ
リブチルペルオキシピバレート、ターシャリブチルペル
オキシジイソブチレート、過酸化ベンゾイル、過酸化ラ
ウロイル、アゾビスイソブチロニトリル、アゾビスジメ
チルバレロニトリル、過硫酸塩−亜硫酸水素塩系等を挙
げることができる。前記ラジカル重合開始剤の含有割合
は、総モノマー重量に対して。The optical resin of the present invention can be obtained by radically polymerizing one or more monomers represented by the general formula (1) above, or by radical polymerizing the monomers represented by the general formula (1) above. It can be obtained by copolymerizing one or more of the above radically polymerizable vinyl monomers. The polymerization or copolymerization method may be a general radical polymerization method such as a bulk polymerization method or a suspension polymerization method, and a cast molding method using bulk polymerization is particularly preferred. Examples of the radical polymerization initiator used in the polymerization or copolymerization include diisopropyl peroxydicarbonate, di-n-propyl peroxydicarbonate, tert-butyl peroxy 2-ethylhexanoate, tert-butyl peroxy pivalate, Examples include tertiary butyl peroxydiisobutyrate, benzoyl peroxide, lauroyl peroxide, azobisisobutyronitrile, azobisdimethylvaleronitrile, persulfate-bisulfite salts, and the like. The content ratio of the radical polymerization initiator is based on the total monomer weight.
０．０１〜１０重量％であることが好ましく、重合温度
２０〜１００℃反応時間０．３〜７２時間の範囲内で反
応さ′せることか望ましい６また本発明において、重合
又は共重合を行う際に、必要に応じて、紫外線吸収剤、
酸化防止剤、染料、顔料、各種安定剤等の添加物を使用
することもできる。The amount is preferably 0.01 to 10% by weight, and the reaction is preferably carried out at a polymerization temperature of 20 to 100°C and a reaction time of 0.3 to 72 hours. If necessary, apply ultraviolet absorber,
Additives such as antioxidants, dyes, pigments, and various stabilizers may also be used.
〈発明の効果〉
本発明の光学用樹脂は、透明性、高屈折率、耐熱性及び
耐衝撃性等の諸物性に非常に優れており、プラスチック
レンズ、光ファイバー、光学素子等の広範にわたり応用
又は、利用することが可能である。<Effects of the Invention> The optical resin of the present invention has excellent physical properties such as transparency, high refractive index, heat resistance, and impact resistance, and can be used in a wide range of applications such as plastic lenses, optical fibers, and optical elements. , it is possible to use it.
〈実施例〉
以下実施例により本発明を更に詳しく説明す゛るが、本
発明はこれらに限定されるものではない。<Examples> The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited thereto.
なお、諸物性は以下の記載する方法により測定した。In addition, various physical properties were measured by the methods described below.
Ｏ屈折率−アツベ屈折計により測定した。O refractive index - Measured using an Atsube refractometer.
Ｏ耐熱性−１３０℃の熱風中に２時間放置後樹脂に変形
、着色等の変化がないものを合格として０とし、不合格
を×とした。O Heat Resistance If the resin showed no change such as deformation or coloring after being left in hot air at -130°C for 2 hours, it was considered to be a pass and was rated 0, and a failure was rated as x.
Ｏ耐衝撃性−厚さ２Ｉの硬化板をＦＤＡ規格に従って試
験を行った。O Impact Resistance - 2I thick cured plates were tested according to FDA specifications.
Ｏ耐溶剤性−硬化樹脂をアセトン、ベンゼン中に室温で
１日夜浸漬し、溶剤に膨潤溶解しないものを合格として
０とし、不合格を×とした。O Solvent Resistance - The cured resin was immersed in acetone and benzene at room temperature for one day and night, and those that did not swell and dissolve in the solvent were evaluated as 0, and those that did not pass were evaluated as x.
裏五孤よ
ナフタレン−２−カルボン酸（ｐ−ビニルベンジル）エ
ステル１０ｇに過酸化ベンゾイル０．２ｇを混合し、７
０℃に加熱した原料を２枚のガラス製（シリコンガスケ
ットを使用）型中に仕込み、８０℃の恒温槽中で１５時
間硬化させた。、更に１００℃にて２時間アニーリング
処理を行なった後、型から樹脂を取り出し前記物性試験
による評価を実施した。その結果を表１に示す。Mix 0.2 g of benzoyl peroxide with 10 g of naphthalene-2-carboxylic acid (p-vinylbenzyl) ester,
The raw materials heated to 0°C were placed in two glass molds (using silicone gaskets) and cured in a constant temperature bath at 80°C for 15 hours. After further annealing at 100° C. for 2 hours, the resin was removed from the mold and evaluated by the physical property test described above. The results are shown in Table 1.
去】１１λ：」−
表１に示す、原料モノマー、ラジカル重合開始剤、硬化
条件にて、実施例１と同様な方法により、得られた樹脂
の物性試験を行い評価した。その結果を表１に示す。11λ:'' - Physical properties of the obtained resin were tested and evaluated in the same manner as in Example 1 using the raw material monomers, radical polymerization initiators, and curing conditions shown in Table 1. The results are shown in Table 1.
生翌五よ二重Five years after birth
Claims (1)
〜４を示す）にて表わされる単量体の１種又は２種以上
を重合させるか若しくは、該単量体の１種又は２種以上
とラジカル重合性モノマーとを共重合させてなる光学用
樹脂。[Claims] The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, m and n are each integers from 0 to 4, and m+n is 1
- 4)), or copolymerize one or more of the monomers with a radically polymerizable monomer. resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27566787A JPH01118802A (en) | 1987-11-02 | 1987-11-02 | Optical resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27566787A JPH01118802A (en) | 1987-11-02 | 1987-11-02 | Optical resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01118802A true JPH01118802A (en) | 1989-05-11 |
Family
ID=17558671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27566787A Pending JPH01118802A (en) | 1987-11-02 | 1987-11-02 | Optical resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01118802A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5851427A (en) * | 1995-03-03 | 1998-12-22 | Rolic Ag | Photocross-linkable naphthyl derivatives |
| WO2017209004A1 (en) * | 2016-05-30 | 2017-12-07 | 日産化学工業株式会社 | Low-viscosity agent for polymerizable compound having high refractive index and polymerizable composition containing same |
| WO2023074408A1 (en) * | 2021-10-28 | 2023-05-04 | 四国化成工業株式会社 | Thiophene compound, method for synthesizing same, and composition containing said thiophene compound |
-
1987
- 1987-11-02 JP JP27566787A patent/JPH01118802A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5851427A (en) * | 1995-03-03 | 1998-12-22 | Rolic Ag | Photocross-linkable naphthyl derivatives |
| WO2017209004A1 (en) * | 2016-05-30 | 2017-12-07 | 日産化学工業株式会社 | Low-viscosity agent for polymerizable compound having high refractive index and polymerizable composition containing same |
| WO2023074408A1 (en) * | 2021-10-28 | 2023-05-04 | 四国化成工業株式会社 | Thiophene compound, method for synthesizing same, and composition containing said thiophene compound |
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