JPH01118801A - Optical resin - Google Patents
Optical resinInfo
- Publication number
- JPH01118801A JPH01118801A JP27566687A JP27566687A JPH01118801A JP H01118801 A JPH01118801 A JP H01118801A JP 27566687 A JP27566687 A JP 27566687A JP 27566687 A JP27566687 A JP 27566687A JP H01118801 A JPH01118801 A JP H01118801A
- Authority
- JP
- Japan
- Prior art keywords
- monomers
- kinds
- formula
- refractive index
- comonomer
- 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 18
- 229920005989 resin Polymers 0.000 title claims abstract description 18
- 230000003287 optical effect Effects 0.000 title claims description 15
- 239000000178 monomer Substances 0.000 claims abstract description 28
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 8
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 238000004040 coloring Methods 0.000 abstract description 2
- -1 vinyl benzyl group Chemical group 0.000 abstract description 2
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical group 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 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
- 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
- 238000000034 method Methods 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 4
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229930016911 cinnamic acid Natural products 0.000 description 4
- 235000013985 cinnamic acid Nutrition 0.000 description 4
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- 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 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 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
- 239000000203 mixture Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 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
- 150000003440 styrenes Chemical class 0.000 description 2
- OIPVGRCXMFBNAN-SNAWJCMRSA-N (e)-3-(2,6-dichlorophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=C(Cl)C=CC=C1Cl OIPVGRCXMFBNAN-SNAWJCMRSA-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
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[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
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 235000014676 Phragmites communis Nutrition 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
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class 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
- 235000019400 benzoyl peroxide Nutrition 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
- 238000006243 chemical reaction Methods 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
- 239000011521 glass 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
- 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
- 239000000049 pigment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer 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
- 239000002994 raw material Substances 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
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic 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、体耐衝撃
性、耐熱性に優れ、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 that has excellent body impact resistance and heat resistance, and has 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
ツジＪ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, toughness, 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 optical distortion, 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
官能上ツマ−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。Therefore, recently, in order to improve these conventional drawbacks, it has been proposed to use a polyfunctional polymer containing a group with a high refractive index as a main component or a modifier. . Specifically, divinylbenzene, diallylphthalates (JP-A-59-81318), dimethacrylate containing bisphenol A (JP-A-55-81318),
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, diallyl phthalate.
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、１．５２〜１．６０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。Even when dimethacrylate and diallyl carbonate containing bisphenol A are used, their cured resins have a low refractive index of 1.52 to 1.60, so they are not suitable for optical resins such as lenses that require a high refractive index. The disadvantage is that the performance is insufficient.
〈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案することにある。<Objective of the Invention> An object of the present invention is to propose 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、下記の一般式（Ｉ）
（式中、Ｘは塩素原子、臭素原子又はヨウ素原子を示し
、ｍは０〜２の整数を示す。）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種以上とコ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) (wherein, X represents a chlorine atom, a bromine atom, or an iodine atom, and m represents an integer of 0 to 2). There is provided an optical resin obtained by polymerizing one or more of the monomers represented by () or copolymerizing one or more of the monomers with a comonomer.
本発明に用いる下記一般式（Ｉ）
式中、Ｘは塩素原子、臭素原子又はヨウ素原子を示し、
ｍは０〜２の整数を示す０ｍが３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することができ
ない、また、式中のエステル残基であるビニルベンジル
基は、ビニル基がオルト、メタ、パラ位のいずれの位置
でもさしつかえないが、合成上パラ位、オルト位のもの
が好ましい。The following general formula (I) used in the present invention, where X represents a chlorine atom, a bromine atom or an iodine atom,
m is an integer from 0 to 2.0 When m is 3 or more, the monomer synthesis becomes complicated and the yield decreases, and the degree of coloration and mechanical strength during polymerization are poor, so it cannot be used. Furthermore, in the vinylbenzyl group which is the ester residue in the formula, the vinyl group may be in any of the ortho, meta, and para positions, but it is preferably in the para or ortho position from the standpoint of synthesis.
本発明に用いる前記一般式（■）にて示される単量体と
しては、例えば、ケイ皮酸（Ｐ−ビニルベンジル）エス
テル、ケイ皮酸（０−ビニルベンジル）エステル、オル
トクロロケイ皮酸（Ｐ−ビニルベンジル）エステル、パ
ラクロロケイ皮酸（Ｐ−ビニルベンジル）エステル、メ
タクロロケイ皮酸（Ｐ−ビニルベンジル）エステル、オ
ルトクロロケイ皮酸（０−ビニルベンジル）エステル、
パラクロロケイ皮酸（０−ビニルベンジル）エステル、
２，６ジクロロケイ皮酸（Ｐ−ビニルベンジル）エステ
ル、バラブロモケイ皮酸（Ｐ−ビニルベンジル）エステ
ル、バラヨードケイ皮酸（Ｐ−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、例えばケイ皮酸とクロロメチルスチレンとを、トル
エンを溶媒としてトリエチルアミンの存在下に脱塩酸し
てエステルを製造する方法等により合成することができ
る。Examples of the monomer represented by the general formula (■) used in the present invention include cinnamic acid (P-vinylbenzyl) ester, cinnamic acid (0-vinylbenzyl) ester, orthochlorocinnamic acid ( P-vinylbenzyl) ester, parachlorocinnamic acid (P-vinylbenzyl) ester, metachlorocinnamic acid (P-vinylbenzyl) ester, orthochlorocinnamic acid (0-vinylbenzyl) ester,
parachlorocinnamic acid (0-vinylbenzyl) ester,
Examples include 2,6 dichlorocinnamic acid (P-vinylbenzyl) ester, valabromocinnamic acid (P-vinylbenzyl) ester, and valaidocinnamic acid (P-vinylbenzyl) ester. The monomer can be synthesized by, for example, a method in which cinnamic acid and chloromethylstyrene are dehydrochlorinated in the presence of triethylamine using toluene as a solvent to produce an ester.
本発明に用いるコモノマーとしては１例えばラジカル重
合性ビニルモノマー又は架橋性官能上ツマー等を好まし
く挙げることができ、前記ラジカル重合性ビニルモノマ
ー又は、架橋性多官能モノマーの具体例としては１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、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、アリル（メタ）アクリレート、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又は、架橋性
多官能七ツマー等のコモノマーの共重合組成比としては
、前記一般式（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
。Preferred comonomers used in the present invention include, for example, radically polymerizable vinyl monomers or crosslinkable functional monomers, and specific examples of the radically polymerizable vinyl monomers or crosslinkable polyfunctional monomers include 1, such as styrene, Methyl nucleus-substituted styrene, halogen-substituted styrene, α-methylstyrene, divinylbenzene, 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, allyl(meth)acrylate, 2-hydroxyethyl (meth)acrylate, polyethylene glycol (meth)acrylate, 1-vinylnaphthalene, 2
-Vinylnaphthalene, diallyl phthalate, diethylene glycol bisallyl carbonate and the like. The copolymerization composition ratio of the radically polymerizable vinyl monomer or comonomer such as a crosslinkable polyfunctional heptamer is 1 to 5000 parts by weight per 100 parts by weight of the monomer represented by the general formula (I). Preferably within the range.
本発明の光学用樹脂は、前記一般式（ｒ）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（Ｉ）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
又は架橋性多官能モノマー等のコ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ート、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、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が望ましい。The optical resin of the present invention can be obtained by radical polymerizing one or more monomers selected from the monomers represented by the above general formula (r), or by radical polymerizing the monomers shown by the above general formula (I). It can be obtained by copolymerizing one or more of these with a comonomer such as the radically polymerizable vinyl monomer or a crosslinkable polyfunctional monomer. 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, and tert-butyl peroxy. Examples include diisobutyrate, benzoyl peroxide, lauroyl peroxide, azobisisobutyronitrile, azobisdimethylvaleronitrile, persulfate-bisulfite salts, and the like. The content ratio of the radical polymerization initiator is preferably 0.01 to 10% by weight based on the total monomer weight, and the reaction is carried out at a polymerization temperature of 20 to 100°C and a reaction time of 0.3 to 72 hours. This is desirable.
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。Furthermore, in the present invention, when performing polymerization or copolymerization, additives such as ultraviolet absorbers, antioxidants, dyes, pigments, and various stabilizers may be used as necessary.
〈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.
◎屈折率−アツベ屈折計により測定した。◎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Ｘとした。O Heat Resistance: Those with no change in the resin such as deformation or coloring after being left in hot air at -130°C for 2 hours were considered to be passed and rated as 0, and those that failed were marked as X.
◎耐衝撃性−厚さ２ｍａ＋の硬化板をＦＤＡ規格に従っ
て試験を行った。◎Impact resistance - 2 ma+ thick hardened plates were tested according to FDA standards.
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.
ス遣」ｕ２
ケイ皮酸（Ｐ−ビニルベンジル）エステルＬｏｇにター
シャリブチルペルオキシピバレート０．２５ ｇを混合
し、２枚のガラス筬（シリコンガスケットを使用）型中
に仕込み、６０℃の恒温槽中で１５時間硬化し、さらに
１００℃で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。0.25 g of tert-butyl peroxypivalate was mixed with cinnamic acid (P-vinylbenzyl) ester Log, and the mixture was placed in two glass reed molds (using silicone gaskets) and kept at a constant temperature of 60°C. After curing in a tank for 15 hours and annealing at 100° C. for 2 hours, the resin was taken out of the mold and evaluated by the physical property test described above.
その結果を表１に示す。The results are shown in Table 1.
去】Ｏ引亀二」−
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。[0]Ohikikameji'' - 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.
凰較五よ二立凰LAN5 YO 2 STATE
Claims (1)
、ｍは０〜２の整数を示す。）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種以上とコモノマーとを共重合させてなる光
学用樹脂。 ２）前記コモノマーがラジカル重合性ビニルモノマー又
は、架橋性多官能モノマーであることを特徴とする特許
請求の範囲第１項記載の光学用樹脂。[Claims] 1) The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, X represents a chlorine atom, a bromine atom, or an iodine atom, and m is 0 to 2 An optical resin obtained by polymerizing one or more of the monomers represented by (representing an integer of ) or copolymerizing one or more of the monomers with a comonomer. 2) The optical resin according to claim 1, wherein the comonomer is a radically polymerizable vinyl monomer or a crosslinkable polyfunctional monomer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27566687A JPH01118801A (en) | 1987-11-02 | 1987-11-02 | Optical resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27566687A JPH01118801A (en) | 1987-11-02 | 1987-11-02 | Optical resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01118801A true JPH01118801A (en) | 1989-05-11 |
Family
ID=17558658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27566687A Pending JPH01118801A (en) | 1987-11-02 | 1987-11-02 | Optical resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01118801A (en) |
-
1987
- 1987-11-02 JP JP27566687A patent/JPH01118801A/en active Pending
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