JPH0255301A - Organic glass - Google Patents
Organic glassInfo
- Publication number
- JPH0255301A JPH0255301A JP20629388A JP20629388A JPH0255301A JP H0255301 A JPH0255301 A JP H0255301A JP 20629388 A JP20629388 A JP 20629388A JP 20629388 A JP20629388 A JP 20629388A JP H0255301 A JPH0255301 A JP H0255301A
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- phthalimide
- refractive index
- vinyl
- vinylphenylmethyl
- 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
- 239000011521 glass Substances 0.000 title claims abstract description 26
- 239000000178 monomer Substances 0.000 claims abstract description 51
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 17
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 14
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 229920001519 homopolymer Polymers 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 8
- 229920001577 copolymer Polymers 0.000 abstract description 4
- -1 N -(m-vinylphenylmethyl)phthalimide Chemical compound 0.000 description 25
- 238000006116 polymerization reaction Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000007870 radical polymerization initiator Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- ZBJMAORHMHEGKX-UHFFFAOYSA-N 2-[(4-ethenylphenyl)methyl]isoindole-1,3-dione Chemical compound C1=CC(C=C)=CC=C1CN1C(=O)C2=CC=CC=C2C1=O ZBJMAORHMHEGKX-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-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
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- OEZWIIUNRMEKGW-UHFFFAOYSA-N (2-bromophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1Br OEZWIIUNRMEKGW-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
- JVPKLOPETWVKQD-UHFFFAOYSA-N 1,2,2-tribromoethenylbenzene Chemical compound BrC(Br)=C(Br)C1=CC=CC=C1 JVPKLOPETWVKQD-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-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
- LGXIMOHTBATHCU-UHFFFAOYSA-N 2,3-di(propan-2-yl)benzenecarboperoxoic acid Chemical compound CC(C)C1=CC=CC(C(=O)OO)=C1C(C)C LGXIMOHTBATHCU-UHFFFAOYSA-N 0.000 description 1
- COGLLVXIBJGDLH-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl hydrogen carbonate Chemical compound OCCOCCOC(O)=O COGLLVXIBJGDLH-UHFFFAOYSA-N 0.000 description 1
- MWBBAKZTTZLVSW-UHFFFAOYSA-N 2-[(2-bromo-4-ethenylphenyl)methyl]isoindole-1,3-dione Chemical compound BrC1=CC(C=C)=CC=C1CN1C(=O)C2=CC=CC=C2C1=O MWBBAKZTTZLVSW-UHFFFAOYSA-N 0.000 description 1
- MYJFKCVPIRAZMM-UHFFFAOYSA-N 2-[(2-chloro-4-ethenylphenyl)methyl]isoindole-1,3-dione Chemical compound ClC1=CC(C=C)=CC=C1CN1C(=O)C2=CC=CC=C2C1=O MYJFKCVPIRAZMM-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- AHWAAQOJHMFNIV-UHFFFAOYSA-N 2-tert-butylperoxy-2-ethylhexanoic acid Chemical compound CCCCC(CC)(C(O)=O)OOC(C)(C)C AHWAAQOJHMFNIV-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 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
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- CJKWEXMFQPNNTL-UHFFFAOYSA-N bis(prop-2-enyl) 1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-5,6-dicarboxylate Chemical compound C=CCOC(=O)C1C(C(=O)OCC=C)C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl CJKWEXMFQPNNTL-UHFFFAOYSA-N 0.000 description 1
- 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 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
- LQKBKHFGCGFBAF-UHFFFAOYSA-N butyl carboxyoxy carbonate Chemical compound CCCCOC(=O)OOC(O)=O LQKBKHFGCGFBAF-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- HVYCQBKSRWZZGX-UHFFFAOYSA-N naphthalen-1-yl 2-methylprop-2-enoate Chemical compound C1=CC=C2C(OC(=O)C(=C)C)=CC=CC2=C1 HVYCQBKSRWZZGX-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、高屈折率、耐候性、透明性、硬度、染色性な
どに優れた有機ガラスに関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an organic glass having high refractive index, excellent weather resistance, transparency, hardness, dyeability, etc.
従来、無機ガラスに代る有機ガラスについては種々研究
されているが、欠点も多く、まだ十分に満足し得る性状
のものは得られていない。例えば、メチルメタクリレー
トやジエチレングリコールビス(了りルカーポネート)
を主成分とする単量体を重合した重合体は、光学材料や
レンズとして使用されているが、その屈折、率は約1.
50と低い。Conventionally, various studies have been conducted on organic glasses to replace inorganic glasses, but they have many drawbacks and have not yet achieved fully satisfactory properties. For example, methyl methacrylate and diethylene glycol carbonate.
Polymers made from monomers whose main component is , are used as optical materials and lenses, but their refractive index is approximately 1.
It's as low as 50.
この欠点を改良した高屈折率樹脂も種々提案されている
。例えば、ポリカーボネート、ポリスルホン系の高屈折
率樹脂が提案されている。これらの樹脂は、屈折率が約
1.60と高いものの、光透過率が低く、光学的均質性
に欠け、また着色するなどの問題がある。Various high refractive index resins have been proposed to improve this drawback. For example, high refractive index resins such as polycarbonate and polysulfone have been proposed. Although these resins have a high refractive index of about 1.60, they have problems such as low light transmittance, lack of optical homogeneity, and coloring.
このため、架橋性の高屈折率樹脂が種々提案されている
。例えば、特開昭61−28901号公報などにフェニ
ル基をハロゲン原子で置換したフェニルメタクリレート
などハロゲン原子を多数含んだ樹脂が提案されている。For this reason, various crosslinkable high refractive index resins have been proposed. For example, resins containing a large number of halogen atoms, such as phenyl methacrylate, in which phenyl groups are substituted with halogen atoms, have been proposed in JP-A-61-28901.
しかし、これらの樹脂は比重が大きくなり、耐候性も劣
る。また、特開昭60−197711号公報などにα−
ナフチルメタクリレートを主成分とする高屈折率樹脂用
組成物が提案されている。これから得られる樹脂は、高
屈折率を有するものの、ナフチル基を有するために耐候
性が劣っている。However, these resins have large specific gravity and poor weather resistance. In addition, α-
A composition for a high refractive index resin containing naphthyl methacrylate as a main component has been proposed. Although the resin obtained from this has a high refractive index, it has poor weather resistance because it contains naphthyl groups.
以上のような先行技術の下で、光学的な用途に好適に使
用し得る有機ガラス、即ち、高屈折率、良好な透明性、
硬度、耐候性、染色性などの諸性質のバランスのとれた
有機ガラスが強く望まれている。Based on the above-mentioned prior art, organic glasses that can be suitably used for optical applications, that is, high refractive index, good transparency,
Organic glasses with well-balanced properties such as hardness, weather resistance, and dyeability are strongly desired.
従って、本発明が解決しようとする課題は、屈折率が1
.590以上で、透明性、硬度、耐候性、染色性等に優
れた有機ガラスを提供することである。Therefore, the problem to be solved by the present invention is that the refractive index is 1.
.. 590 or higher and has excellent transparency, hardness, weather resistance, dyeability, etc.
本発明者らは、上記の課題を解決するために鋭意研究を
重ねた結果、特定の構造を有するビニル単量体を重合し
て得た重合体が、上記の諸性質を具備した優れた有機ガ
ラスとなり得ることを見い出し、本発明を完成するに至
った。As a result of extensive research to solve the above problems, the present inventors have discovered that a polymer obtained by polymerizing a vinyl monomer having a specific structure is an excellent organic material with the above properties. They discovered that it could be made into glass and completed the present invention.
即ち、本発明は、 (八)下記一般式CI) で示されるビニル単量体く以下単量体(A)ともいう。That is, the present invention (8) General formula CI below) The vinyl monomer shown below is also referred to as monomer (A).
)
及び
(B)上記のビニル単量体と共重合可能な他の単量体で
あって、単独重合体の屈折率が1.560以上であるラ
ジカル重合可能な単量体(以下、単量体(B) とも
いう。)
を共重合してなる有機ガラスである。) and (B) other monomers that can be copolymerized with the above vinyl monomer, and whose homopolymer has a refractive index of 1.560 or more (hereinafter referred to as monomers) It is an organic glass made by copolymerizing the following:
前記一般式(1)中、Rはアルキレン基であれば良く、
その炭素数には特に制限されないが、−般に炭素数1〜
10個の直鎖又は分枝のアルキレン基が好ましい。特に
重合して得られる有機ガラスの屈折率の観点から炭素数
1〜4個の直鎖又は分枝のアルキレン基が好ましい。ま
た、X+、Xz、Xl、X4、Zl、Z2、Z3及びZ
4は、夫々同種又は異種の水素原子、ハロゲン原子又は
ビニル基であって、ハロゲン原子としては、得られる有
機ガラスの耐候性の観点から塩素原子又は臭素原子が特
に好適に用いられる。さらに、一般式(1)で示される
ビニル単量体中のハロゲン原子数が多いほど得られる樹
脂の屈折率は増加するが、同時に比重が増大し、耐候性
が不良となるため、一般式CI)で示されるビニル単量
体−分子中のハロゲン原子の数は、0〜4となるよう選
択することが好ましい。また、一般式[1)で示される
ビニル重量体−分子中のビニル基の数は、得られる樹脂
の耐候性の観点から1〜3となるよう選択することが好
ましい。In the general formula (1), R may be an alkylene group,
The number of carbon atoms is not particularly limited, but generally has 1 to 1 carbon atoms.
Preference is given to 10 straight-chain or branched alkylene groups. In particular, from the viewpoint of the refractive index of the organic glass obtained by polymerization, a linear or branched alkylene group having 1 to 4 carbon atoms is preferred. Also, X+, Xz, Xl, X4, Zl, Z2, Z3 and Z
4 is the same or different hydrogen atom, halogen atom, or vinyl group, and as the halogen atom, a chlorine atom or a bromine atom is particularly preferably used from the viewpoint of weather resistance of the resulting organic glass. Furthermore, as the number of halogen atoms in the vinyl monomer represented by general formula (1) increases, the refractive index of the resulting resin increases, but at the same time, the specific gravity increases and weather resistance deteriorates. The number of halogen atoms in the vinyl monomer molecule represented by ) is preferably selected from 0 to 4. Further, the number of vinyl groups in the vinyl heavy molecule represented by the general formula [1] is preferably selected to be 1 to 3 from the viewpoint of weather resistance of the resulting resin.
本発明に於いて好適に使用される前記一般弐N)で示さ
れるビニル単量体を具体的に例示すれば次の通りである
。Specific examples of vinyl monomers represented by general 2N) that are preferably used in the present invention are as follows.
N−(0−ビニルフェニルメチル)フタルイミド、N
−(m−ビニルフェニルメチル)フタルイミド、N−(
p−ビニルフェニルメチル)フタルイミド、N−(o−
ビニルフェニルエチル)フタルイミド、N −(m−ビ
ニルフェニルプロピル)フタルイミド、N−(p−ビニ
ルフェニル−4s。N-(0-vinylphenylmethyl)phthalimide, N
-(m-vinylphenylmethyl)phthalimide, N-(
p-vinylphenylmethyl)phthalimide, N-(o-
vinylphenylethyl)phthalimide, N-(m-vinylphenylpropyl)phthalimide, N-(p-vinylphenyl-4s).
プロピル)フタルイミド、N−(m−ビニルフェニルブ
チル)フタルイミド、N−(2−クロロ−4−ビニルフ
ェニルメチル)フタルイミド、N−(3−クロロ−4−
ビニルフェニルメチル)フタルイミド、N−(2−ブロ
モ−4−ビニルフェニルメチル)フタルイミド、N−(
2−プロモ3−ビニルフェニルメチル)フタルイミド、
N−(5−ブロモ−3−ビニルフェニルメチル)フタル
イミド、N−(2,6−ジクロロ−4−ビニルフェニル
メチル)フタルイミド、N−(3,5−ジブロモ−4−
ビニルフェニルメチル)フタルイミド、N−(4−クロ
ロ−2−ビニルフェニルエチル)フタルイミド、3−ク
ロロ−N−(p−ビニルフェニルメチル)フタルイミド
、4−クロロN −(m−ビニルフェニルエチル)フタ
ルイミド、4,5−ジクロロ−N −(m−ビニルフェ
ニルメチル)フタルイミド、4−ブロモ−N −(mビ
ニルフェニルメチル)フタルイミド、3.6ジプロモー
N −(p−ビニルフェニルメチル)フタルイミド、2
.3.4−トリクロロ−N−(0−ビニルフェニルメチ
ル)フタルイミド、2゜3.4.5−テトラクロロ−N
−(m−ビニルフェニルメチル)フタルイミド、3−ク
ロロ−N(1′−クロロ−4′−ビニルフェニルメチル
〕フタルイミド、4,5−ジクロロ−N−(2’ブロモ
−5′−ビニルフェニルメチル)フタルイミド、N−(
3,5−ジビニルフェニルメチル)フタルイミド、3−
ブロモ−N−(3’、5’ジビニルフエニルメチル)フ
タルイミド、3−ビニル−N−(4’−ビニルフェニル
メチル)フタルイミド、4,5−ジビニル−N−(3’
−ビニルフェニルメチル)フタルイミドなどが例示され
る。propyl)phthalimide, N-(m-vinylphenylbutyl)phthalimide, N-(2-chloro-4-vinylphenylmethyl)phthalimide, N-(3-chloro-4-
Vinylphenylmethyl)phthalimide, N-(2-bromo-4-vinylphenylmethyl)phthalimide, N-(
2-promo3-vinylphenylmethyl)phthalimide,
N-(5-bromo-3-vinylphenylmethyl)phthalimide, N-(2,6-dichloro-4-vinylphenylmethyl)phthalimide, N-(3,5-dibromo-4-
vinylphenylmethyl)phthalimide, N-(4-chloro-2-vinylphenylethyl)phthalimide, 3-chloro-N-(p-vinylphenylmethyl)phthalimide, 4-chloroN-(m-vinylphenylethyl)phthalimide, 4,5-dichloro-N-(m-vinylphenylmethyl)phthalimide, 4-bromo-N-(m-vinylphenylmethyl)phthalimide, 3.6-dibromo-N-(p-vinylphenylmethyl)phthalimide, 2
.. 3.4-Trichloro-N-(0-vinylphenylmethyl)phthalimide, 2゜3.4.5-tetrachloro-N
-(m-vinylphenylmethyl)phthalimide, 3-chloro-N(1'-chloro-4'-vinylphenylmethyl)phthalimide, 4,5-dichloro-N-(2'bromo-5'-vinylphenylmethyl) Phthalimide, N-(
3,5-divinylphenylmethyl)phthalimide, 3-
Bromo-N-(3',5'divinylphenylmethyl)phthalimide, 3-vinyl-N-(4'-vinylphenylmethyl)phthalimide, 4,5-divinyl-N-(3'
-vinylphenylmethyl)phthalimide and the like.
また、本発明の有機ガラスのもう一方の構成成分は、前
記一般式(+)で示されるビニル単量体と共電可能な他
の単量体であって、単独重合体の屈折率が1.560以
上であるラジカル重合可能な単量体である。このような
単量体を例示すれば、メタクリル酸ベンジル・ナクリル
酸フェニル、メタクリル酸ブロモフェニル、ビスフェノ
ールAジメタクリレート、2.2’、6.6’−テトラ
ブロモビスフェノールAジアクリレート、ビスフェノー
ルSジメタクリレートなどのメタクリル酸エステル及び
アクリル酸エステル類;スチレン、クロロスチレン、ブ
ロモスチレン、ジプロモスチレン、トリブロモスチレン
、ジビニルベンゼン、ビニルナフタレンなどのスチレン
類ニジアリルフタレート、ジアリルイソフタレート、ク
ロレンド酸ジアリルなどのアリル化合物類など及びこれ
らの混合物などである。The other component of the organic glass of the present invention is another monomer capable of co-electrifying with the vinyl monomer represented by the general formula (+), and the refractive index of the homopolymer is 1. It is a radically polymerizable monomer with a molecular weight of .560 or higher. Examples of such monomers include benzyl methacrylate, phenyl nacrylate, bromophenyl methacrylate, bisphenol A dimethacrylate, 2.2',6.6'-tetrabromobisphenol A diacrylate, and bisphenol S dimethacrylate. Methacrylic acid esters and acrylic esters such as styrene, chlorostyrene, bromostyrene, dipromostyrene, tribromostyrene, divinylbenzene, vinylnaphthalene, etc. Allyls such as diallyl phthalate, diallyl isophthalate, diallyl chlorendate, etc. Compounds, etc. and mixtures thereof.
本発明に於いて、単量体(A)及び単量体(B)の組成
割合は、それぞれの単量体の種類によって好適な割合が
あるために一般に限定できないが、総じて一般式(1)
で表わされる単量体(A)が20〜70重量%の範囲で
好ましくは用いられ、より好ましくは30〜60重量%
の範囲で使用される。In the present invention, the composition ratio of monomer (A) and monomer (B) cannot be generally limited because there is a suitable ratio depending on the type of each monomer, but generally, the composition ratio of monomer (A) and monomer (B)
The monomer (A) represented by is preferably used in a range of 20 to 70% by weight, more preferably 30 to 60% by weight.
used within the range.
また、本発明の有機ガラスを玉摺り加工あるいは切削加
工を必要とする用途に用いる場合には、前記単量体(A
)又は(B)のいずれかが架橋性であることが好ましい
。即ち、単量体(A)が−官能性の単量体の場合は、単
量体(B)の一部又はすべてが二官能性以上の架橋性の
単量体であることが好ましい。In addition, when the organic glass of the present invention is used for applications requiring beading or cutting, the monomer (A
) or (B) is preferably crosslinkable. That is, when the monomer (A) is a -functional monomer, it is preferable that a part or all of the monomer (B) is a bifunctional or higher crosslinkable monomer.
単量体(A)と単量体(B)の共重合方法は、特に限定
的でなく、公知の注型重合方法を採用できる。The method of copolymerizing monomer (A) and monomer (B) is not particularly limited, and any known cast polymerization method can be employed.
重合開始手段は、種々の過酸化物やアゾ化合物等のラジ
カル重合開始剤の使用、又は紫外線、α線、β線、T線
等の照射或いは両者の併用によって行うことができる。Polymerization initiation means can be carried out by using radical polymerization initiators such as various peroxides and azo compounds, by irradiation with ultraviolet rays, α-rays, β-rays, T-rays, etc., or by using a combination of both.
代表的な重合方法を例示すると、エラストマーガスケッ
トまたはスペーサーで保持されているモールド間に、ラ
ジカル重合開始剤を含む前記の単量体混合物を注入し、
空気炉中で硬化させた後、取出せばよい。To illustrate a typical polymerization method, the above monomer mixture containing a radical polymerization initiator is injected between molds held by an elastomer gasket or spacer,
It can be cured in an air oven and then taken out.
ラジカル重合開始剤としては、特に限定されず、公知の
ものが使用できるが、代表的なものを例示すると、ベン
ゾイルパーオキサイド、p−クロロベンゾイルパーオキ
サイド、デカノイルパーオキサイド、ラウロイルパーオ
キサイド、アセチルパーオキサイド等のジアシルパーオ
キサイド;tブチルパーオキシ−2−エチルヘキサネー
ト、を−ブチルパーオキシネオデカネート、クミルパー
オキシネオデカネート、t−ブチルパーオキシベンゾエ
ート等のパーオキシエステル;ジイソプロピルパーオキ
シジカーボネ゛−ト、ジー2−エチルへキシルパーオキ
シジカーボネート、ジーSec 7プチルパーオキシジ
カーボネート等のパーカーボネート;アゾビスイソブチ
ロニトリル等のアゾ化合物である。該ラジカル重合開始
剤の使用量は、重合条件や開始剤の種類、前記の単量体
混合物の組成によって異なり、−概に限定できないが、
般には、全単量体100重量部に対して0.01〜10
重量部、好ましくはo、oi〜5重量部の範囲で用いる
のが好適である。The radical polymerization initiator is not particularly limited and any known one can be used, but representative examples include benzoyl peroxide, p-chlorobenzoyl peroxide, decanoyl peroxide, lauroyl peroxide, and acetyl peroxide. Diacyl peroxides such as oxide; peroxy esters such as t-butylperoxy-2-ethylhexanate, -butylperoxyneodecanate, cumylperoxyneodecanate, t-butylperoxybenzoate; diisopropylperoxybenzoate; carbonates, percarbonates such as di-2-ethylhexyl peroxydicarbonate and di-Sec 7 butyl peroxydicarbonate; and azo compounds such as azobisisobutyronitrile. The amount of the radical polymerization initiator used varies depending on the polymerization conditions, the type of initiator, and the composition of the monomer mixture, and cannot be generally limited.
Generally, 0.01 to 10 parts by weight per 100 parts by weight of total monomers.
It is suitable to use it in parts by weight, preferably in the range of o, oi to 5 parts by weight.
重合条件のうち、特に温度は得られる有機ガラスの性状
に影響を与える。この温度条件は、開始剤の種類と量や
単量体の種類によって影響を受けるので、−概に限定は
できないが、−船釣に比較的低温下で重合を開始し、ゆ
っくりと温度をあげて行き、重合終了時に高温下に硬化
させる所謂テーパ型の2段重合を行うのが好適である。Among polymerization conditions, temperature particularly affects the properties of the resulting organic glass. This temperature condition is affected by the type and amount of initiator and the type of monomer, so - although it cannot be generalized - polymerization is started at a relatively low temperature and the temperature is slowly raised. It is preferable to carry out so-called tapered two-stage polymerization, in which the polymer is cured under high temperature at the end of polymerization.
重合時間も温度と同様に各種の要因によって異なるので
、予めこれらの条件に応じた最適の時間を決定するのが
好適であるが、一般に2〜40時間で重合が完結するよ
うに条件を選ぶのが好ましい。Like temperature, polymerization time also varies depending on various factors, so it is preferable to determine the optimal time according to these conditions in advance, but in general, conditions should be selected so that polymerization is completed in 2 to 40 hours. is preferred.
勿論、前記重合に際し、離型剤、紫外線吸収剤、酸化防
止剤、着色防止剤、帯電防止剤、ケイ光染料、染料、顔
料等の各種安定剤、添加剤は必要に応じて選択して使用
することが出来る。Of course, during the polymerization, various stabilizers and additives such as release agents, ultraviolet absorbers, antioxidants, color inhibitors, antistatic agents, fluorescent dyes, dyes, and pigments may be selected and used as necessary. You can.
さらに、上記の方法で得られる有機ガラスは、その用途
に応じて以下のような処理を施すことも出来る。即ち、
分散染料などの染料を用いる染色、シランカップリング
剤やケイ素、ジルコニウム、アンチモン、アルミニウム
等の酸化物のゾルを主成分とするハードコート剤や、有
機高分子体を主成分とするハードコート剤によるハード
コーティング処理や、SiO□、TiO□、ZrO等の
金属酸化物の薄膜の蒸着や有機高分子体の薄膜の塗布等
による反射防止処理、帯電防止処理等の加工及び2次処
理を施すことも可能である。Furthermore, the organic glass obtained by the above method can also be subjected to the following treatments depending on its use. That is,
Dyeing using dyes such as disperse dyes, hard coating agents mainly composed of silane coupling agents, sol of oxides such as silicon, zirconium, antimony, aluminum, etc., and hard coating agents mainly composed of organic polymers. Processing and secondary treatments such as hard coating treatment, anti-reflection treatment by vapor deposition of thin films of metal oxides such as SiO□, TiO□, and ZrO, and coating of thin films of organic polymers, antistatic treatment, etc. can also be performed. It is possible.
本発明により得られる有機ガラスは、単量体(八)と単
量体(B)との共重合により得られる共重合体である。The organic glass obtained by the present invention is a copolymer obtained by copolymerizing monomer (8) and monomer (B).
この共重合体は、屈折率が1.590以上で無色透明で
あり、表面硬度、染色性、耐候性等にも優れている。従
って、本発明により得られる有機ガラスは、例えば、メ
ガネレンズ、光学機器レンズ等の光学レンズに最適であ
り、その他プリズム;光ディスク基板;光ファイバー等
の用途に好適に使用することができる。This copolymer has a refractive index of 1.590 or more, is colorless and transparent, and has excellent surface hardness, dyeability, weather resistance, etc. Therefore, the organic glass obtained by the present invention is suitable for optical lenses such as eyeglass lenses and optical equipment lenses, and can also be suitably used for other applications such as prisms, optical disk substrates, and optical fibers.
以下、本発明を具体的に説明するために、実施例を挙げ
て説明するが、本発明はこれらの実施例に限定されるも
のではない。EXAMPLES Hereinafter, in order to specifically explain the present invention, Examples will be given and explained, but the present invention is not limited to these Examples.
なお、実施例において得られた有機ガラスは、下記の試
験法によって諸物性を測定した。In addition, various physical properties of the organic glasses obtained in the examples were measured by the following test methods.
(11屈折率
アツベの屈折計を用いて20℃においる屈折率を測定し
た。接触液には、ブロモナフタリンを使用した。(The refractive index at 20° C. was measured using an Atsube refractometer with a refractive index of 11. Bromonaphthalene was used as the contact liquid.
(2)硬度
ロックウェル硬度計を用い、厚さ2鶴の試験片について
L−スケールの値を測定した。(2) Hardness Using a Rockwell hardness meter, the L-scale value was measured for a test piece with a thickness of 2 cranes.
(3)外観 目視により判定した。(3) Appearance Judgment was made visually.
(4)染色性
分散染料(眼部セイコー−の製品名ビスタブラウン)を
ljl!の水に2g分散させ、90℃に加熱し、染色可
能なものを○、染色できないものを×で評価した。(4) Dyeable disperse dye (product name Vista Brown from Eye Seiko)! 2g was dispersed in water and heated to 90° C., and those that could be dyed were evaluated as ○, and those that could not be dyed were evaluated as ×.
(5)耐候性
スガ試験a側製ロングライフキセノンフェードメーター
(FAC−25AX−1(C型)中に試料を設置し、1
00時間キセノン光を露光した後、試料の表面状態を目
視で観察し、・ポリスチレンに比べ着色の程度の低いも
のを○、同等のものを△、高いものを×で評価した。(5) Place the sample in a long-life xenon fade meter (FAC-25AX-1 (C type)) manufactured by Suga Test A side,
After being exposed to xenon light for 00 hours, the surface condition of the sample was visually observed and evaluated as ○ if the degree of coloring was lower than that of polystyrene, △ if it was the same, and × if it was high.
尚、以下の実施例で使用した単量体は、下記の記号で表
わした。但し、〔〕内は単独重合体の屈折率である。In addition, the monomers used in the following examples are represented by the following symbols. However, the number in [ ] is the refractive index of the homopolymer.
p−MP : N−(p−ビニルフェニルメチル)フタ
ルイミド
m−MP:N−(m−ビニルフェニルメチル)フタルイ
ミド
BP:N−(m−ビニルフェニルエチル)フタルイミド
BrMP :4−ブロモーN−(m−ビニル7工Br
BP
(1’!M P
C1’、MP
MP
αSt
VB
2MA
DMA
ニルメチル)フタルイミド
:N−(2−ブロモ−5−ビニルフェ
ニルブチル)フタルイミド
:N−(2,6−ジクロロ−4−ビニ
ルフェニルメチル)フタルイミド
:3,4,5.6−チトラクロローN
−(p−ビニルフェニルメチル)フ
タルイミド
:N−(2,4−ジビニルフェニルメ
チル)フタルイミド
:スチレン (1,590):クロロスチレ
ン(0体、m体の
混合物) (1,610)ニジビニルベ
ンゼン (1,615):ベンジルメタクリレート
(1,568)
:2.2’、6.6’−テトラブ
ロモビスフェノールAジメタク
リレー) (1,6043実施例1
第1表に示す単量体(A)50重量部と単量体(B)と
してスチレン50重量部の混合物100重量部と対して
ラジカル重合開始剤としてベンゾイルパーオキシド1重
量部を添加しよく混合した。この混合液をガラス板とエ
チレン−酢酸ビニル共重合体とから成るガスケットで構
成された鋳型の中へ注入し、注型重合を行った。重合は
、空気炉を用い、80℃から30℃で18時間かけ、徐
々に温度を上げて行き、1,30℃に2時間保持した。p-MP: N-(p-vinylphenylmethyl)phthalimide m-MP: N-(m-vinylphenylmethyl)phthalimide BP: N-(m-vinylphenylethyl)phthalimide BrMP: 4-bromo N-(m- Vinyl 7k Br
BP (1'!M P C1', MP MP αSt VB 2MA DMA Nylmethyl)phthalimide: N-(2-bromo-5-vinylphenylbutyl)phthalimide: N-(2,6-dichloro-4-vinylphenylmethyl) Phthalimide: 3,4,5,6-titrachloro N -(p-vinylphenylmethyl) phthalimide: N-(2,4-divinylphenylmethyl) phthalimide: Styrene (1,590): Chlorostyrene (0 form, m form mixture) (1,610) Nidivinylbenzene (1,615): Benzyl methacrylate (1,568): 2.2', 6.6'-tetrabromobisphenol A dimethacrylate) (1,6043 Example 1 1st To 100 parts by weight of a mixture of 50 parts by weight of monomer (A) shown in the table and 50 parts by weight of styrene as monomer (B), 1 part by weight of benzoyl peroxide as a radical polymerization initiator was added and mixed well. This mixed solution was injected into a mold consisting of a gasket made of a glass plate and an ethylene-vinyl acetate copolymer, and cast polymerization was performed.Polymerization was performed at 80 to 30 °C using an air furnace. The temperature was gradually raised over 18 hours and maintained at 1.30°C for 2 hours.
重合終了後、鋳型を空気炉から取出し、放冷後、重合体
を鋳型のガラスからとりはずした。得られた有機ガラス
の諸物性を測定して第1表に示した。After the polymerization was completed, the mold was taken out from the air oven, and after cooling, the polymer was removed from the glass mold. Various physical properties of the obtained organic glass were measured and shown in Table 1.
実施例2
第2表に示す単量体(八)及び単量体(II)から成る
組成物を用いた以外、実施例1と全く同様に実施した。Example 2 The same procedure as in Example 1 was carried out except that a composition consisting of monomer (8) and monomer (II) shown in Table 2 was used.
得られた有機ガラスの物性を測定して、第2表に示した
。The physical properties of the obtained organic glass were measured and shown in Table 2.
実施例3
第3表に示す、3種の単量体混合物を用いた以外、全て
実施例1と同様に実施した。得られた有機ガラスの物性
を第3表に示した。Example 3 The same procedure as in Example 1 was carried out except that a mixture of three monomers shown in Table 3 was used. The physical properties of the obtained organic glass are shown in Table 3.
Claims (1)
3、X_4、Z_1、Z_2、Z_3及びZ_4は、夫
々同種又は異種の水素原子、ハロゲン原子又はビニル基
である。 で示されるビニル単量体 及び (B)上記のビニル単量体と共重合可能な他の単量体で
あって、単独重合体の屈折率が1.560以上であるラ
ジカル重合可能な単量体 を共重合してなる有機ガラス。(1) (A) General formula below ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ However, R is an alkylene group, X_1, X_2, X_
3, X_4, Z_1, Z_2, Z_3 and Z_4 are the same or different hydrogen atoms, halogen atoms or vinyl groups, respectively. Vinyl monomers represented by (B) other monomers copolymerizable with the above vinyl monomers, which are radically polymerizable monomers with a homopolymer refractive index of 1.560 or more Organic glass made by copolymerizing bodies.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP20629388A JPH0255301A (en) | 1988-08-22 | 1988-08-22 | Organic glass |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP20629388A JPH0255301A (en) | 1988-08-22 | 1988-08-22 | Organic glass |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0255301A true JPH0255301A (en) | 1990-02-23 |
Family
ID=16520905
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP20629388A Pending JPH0255301A (en) | 1988-08-22 | 1988-08-22 | Organic glass |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0255301A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7215884B2 (en) | 2003-06-24 | 2007-05-08 | Samsung Electronics Co., Ltd. | Optical demultiplexer having bragg diffration grating and optical communication module using the optical demultiplexer |
JP2008009426A (en) * | 2006-06-02 | 2008-01-17 | Fujifilm Corp | Pigment dispersion composition, photo-curing composition, color filter using the same, and manufacturing method of the color filter |
KR20160030172A (en) * | 2013-07-09 | 2016-03-16 | 에보니크 데구사 게엠베하 | Electroactive polymers, manufacturing process thereof, electrode and use thereof |
-
1988
- 1988-08-22 JP JP20629388A patent/JPH0255301A/en active Pending
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7215884B2 (en) | 2003-06-24 | 2007-05-08 | Samsung Electronics Co., Ltd. | Optical demultiplexer having bragg diffration grating and optical communication module using the optical demultiplexer |
JP2008009426A (en) * | 2006-06-02 | 2008-01-17 | Fujifilm Corp | Pigment dispersion composition, photo-curing composition, color filter using the same, and manufacturing method of the color filter |
KR20160030172A (en) * | 2013-07-09 | 2016-03-16 | 에보니크 데구사 게엠베하 | Electroactive polymers, manufacturing process thereof, electrode and use thereof |
JP2016531971A (en) * | 2013-07-09 | 2016-10-13 | エボニック デグサ ゲーエムベーハーEvonik Degussa GmbH | Electroactive polymer, method for producing the same, electrode and use thereof |
US10103384B2 (en) | 2013-07-09 | 2018-10-16 | Evonik Degussa Gmbh | Electroactive polymers, manufacturing process thereof, electrode and use thereof |
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JPS63251408A (en) | Resin of high refractive index | |
JPH0679083B2 (en) | Optical material |