JPH0718041A - Resin composition - Google Patents
Resin compositionInfo
- Publication number
- JPH0718041A JPH0718041A JP18341893A JP18341893A JPH0718041A JP H0718041 A JPH0718041 A JP H0718041A JP 18341893 A JP18341893 A JP 18341893A JP 18341893 A JP18341893 A JP 18341893A JP H0718041 A JPH0718041 A JP H0718041A
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- weight
- parts
- refractive index
- dyeability
- 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.)
- Granted
Links
- 239000011342 resin composition Substances 0.000 title claims description 9
- 239000000178 monomer Substances 0.000 claims abstract description 37
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 15
- HWYBMDXOCIQPEZ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;4-(4-sulfanylphenyl)sulfanylbenzenethiol Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.C1=CC(S)=CC=C1SC1=CC=C(S)C=C1 HWYBMDXOCIQPEZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 11
- 238000004043 dyeing Methods 0.000 claims description 10
- 238000005266 casting Methods 0.000 claims description 4
- 238000000465 moulding Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 16
- 125000003118 aryl group Chemical group 0.000 abstract description 11
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract description 5
- 125000004434 sulfur atom Chemical group 0.000 abstract description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract description 2
- -1 bisphenol A ester Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 description 38
- 150000001875 compounds Chemical class 0.000 description 14
- 239000011347 resin Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 238000002834 transmittance Methods 0.000 description 9
- 229920003023 plastic Polymers 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000000986 disperse dye Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-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
- 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
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 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
- 238000005498 polishing Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、染色性に富む高屈折率
樹脂組成物に関する。更に詳しく述べるなら、染色性に
富む屈折率１．５８以上の眼鏡レンズに適した高屈折率
樹脂組成物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a high-refractive-index resin composition having excellent dyeability. More specifically, it relates to a high refractive index resin composition suitable for a spectacle lens having a dyeability of 1.58 or more.
【０００２】[0002]
【従来の技術】一般に眼鏡レンズとして用いられる樹脂
材料は、軽く、強度があり、染色性に富むことが求めら
れる。特に、従来のガラス製の材料では、全く得られな
い性質である染色性は眼鏡レンズとして用いられる樹脂
材料に具備すべき必須の極めて重要な特性である。特
に、可視光線波長域の透過率が２０％を下回る程度まで
の染色が求められる場合も少なくない。従来、眼鏡レン
ズとして用いられる樹脂材料の内、ジエチレングリコ−
ルビスアリルカ−ボネ−トは、優れた染色性を示し、現
在最も眼鏡レンズ用樹脂として多用される材料である。
しかし、上記ジエチレングリコ−ルビスアリルカ−ボネ
−トを重合して得られる樹脂は、屈折率が低く、１．５
０であるため眼鏡レンズとした場合、特に凹レンズのこ
ばが非常に厚くなる欠点があった。この為、屈折率が高
いプラスチック製の材料が強く望まれている。しかしな
がら、屈折率が高い材料は、一般には、芳香族性が大き
く疎水性の材料となる傾向がある。一般に、レンズの染
色方法は、分散染料を水に分散させ、加温することによ
る。このため、芳香族性が大きく疎水性の屈折率が高い
材料は、一般に、染色が困難になる傾向がある。この意
味から、プラスチック製の眼鏡材料であって、屈折率が
比較的高く、高度に染色性に富む材料が強く望まれてい
る。2. Description of the Related Art Generally, a resin material used for an eyeglass lens is required to be light, strong and highly dyeable. In particular, the dyeability, which is a property that cannot be obtained by conventional glass materials, is an essential and extremely important property that resin materials used as spectacle lenses should have. In particular, there are many cases where dyeing is required until the transmittance in the visible light wavelength range falls below 20%. Among the resin materials conventionally used as spectacle lenses, diethylene glycol-
Rubisallyl carbonate shows excellent dyeability and is currently the most frequently used resin for eyeglass lenses.
However, the resin obtained by polymerizing the above diethylene glycol bisallyl carbonate has a low refractive index of 1.5
Since it is 0, there is a defect that the dent of the concave lens becomes extremely thick when used as a spectacle lens. Therefore, a plastic material having a high refractive index is strongly desired. However, materials with a high refractive index generally tend to be highly aromatic and hydrophobic. Generally, a method of dyeing a lens is to disperse a disperse dye in water and heat the dispersion. Therefore, in general, a material having a large aromaticity and a hydrophobicity and a high refractive index tends to be difficult to dye. From this point of view, there is a strong demand for a plastic eyeglass material having a relatively high refractive index and a high dyeability.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、以上の要請
に応え、プラスチック製の眼鏡材料であって、屈折率が
比較的高く、染色性に富む有用な高屈折率材料組成物を
提供することを目的とする。SUMMARY OF THE INVENTION The present invention meets the above requirements and provides a useful high refractive index material composition which is a plastic spectacle material having a relatively high refractive index and rich dyeability. The purpose is to
【０００４】[0004]
【課題を解決するための手段】本発明の樹脂組成物は、
特定の芳香族基と硫黄原子を有する下記化３〔構造式
（１）〕で示される４，４’ーチオビスベンゼンチオ−
ルジメタクリレ−ト単量体と、芳香族基とエチレンオキ
シドユニットを有する下記化４〔構造式（２）〕で示さ
れる芳香族単量体を主成分とするモノマ−混合物をラジ
カルキャスト重合成形を行うことにより得られる有用な
樹脂組成物である。The resin composition of the present invention comprises:
4,4′-thiobisbenzenethio-having a specific aromatic group and a sulfur atom represented by the following chemical formula 3 [structural formula (1)]
Radical cast polymerization of a rudimethacrylate monomer and a monomer mixture containing an aromatic group and an ethylene oxide unit and having an aromatic monomer represented by the following chemical formula 4 [Structural formula (2)] as a main component. It is a useful resin composition obtained by.
【０００５】本発明の眼鏡レンズに適した樹脂組成物
は、特定のモノマ−のラジカルキャスティング重合によ
って得られる。本発明において用いられるモノマ−は、
次のような特定の単量体が用いられる。即ち、特定の芳
香族基と３個の硫黄原子を有する下記構造式（１）で示
される４，４’ーチオビスベンゼンチオ−ルジメタクリ
レ−ト、及び芳香族基とエチレンオキシドユニットを有
する構造式（２）で示される２官能単量体を主成分とす
る。The resin composition suitable for the spectacle lens of the present invention is obtained by radical casting polymerization of a specific monomer. The monomer used in the present invention is
The following specific monomers are used. That is, 4,4′-thiobisbenzenethiol dimethacrylate represented by the following structural formula (1) having a specific aromatic group and three sulfur atoms, and a structural formula (a) having an aromatic group and an ethylene oxide unit ( The main component is the bifunctional monomer represented by 2).
【０００６】[0006]
【化３】 [Chemical 3]
【０００７】[0007]
【化４】 [Chemical 4]
【０００８】本発明に於て、構造式（１）のジメタクリ
ルエステルが芳香族基及び多数の硫黄原子を、又構造式
（２）でビスフェノ−ルＡ型の芳香族基を有するエステ
ルが用いられる理由は、これらを含有することによっ
て、本発明の眼鏡材料用組成物の屈折率を比較的高くす
ることが出来るためである。構造式（１）の４，４’ー
チオビスベンゼンチオ−ルジメタクリレ−ト単量体は、
上述の様に芳香族基及び多数の硫黄原子を有することか
ら極めて高い屈折率を有し、有用な材料ではあるが、こ
れだけでは有用な眼鏡レンズを作ることはできない。そ
の理由は、構造式（１）の単量体は、常温で固体であ
り、又非常に芳香族性が高く疎水性が強いため、通常構
造式（１）から作られる重合体は、染色性を有し得な
い。この為構造式（１）の共重合相手は、常温で液体で
あり且つ共重合組成物が染色性に富む材料である必要が
ある。In the present invention, an ester having an aromatic group and a large number of sulfur atoms as the dimethacrylic ester of the structural formula (1) and an ester having a bisphenol A type aromatic group as the structural formula (2) is used. The reason for this is that by containing these, the refractive index of the composition for eyeglass material of the present invention can be made relatively high. The 4,4′-thiobisbenzenethiol dimethacrylate monomer of structural formula (1) is
Since it has an extremely high refractive index because it has an aromatic group and a large number of sulfur atoms as described above, and it is a useful material, it cannot make a useful spectacle lens by itself. The reason for this is that the monomer of structural formula (1) is solid at room temperature and has a high aromaticity and a high hydrophobicity. Can not have. Therefore, the copolymerization partner of the structural formula (1) needs to be a material that is liquid at room temperature and has a rich dyeability in the copolymerization composition.
【０００９】本発明で使用される構造式（２）の単量体
は、この様な背景から生まれた単量体である。構造式
（２）の化合物は、特に、屈折率を大きくする目的のた
めには、ビスフェノ−ルＡ型の芳香族基の含量を多くす
る必要があり、ポリエトキシ基は、少ない方がよい。し
かしながら、この化合物だけで得られる樹脂は、疎水性
が高く目的とする染色性に富む材料となりにくい。この
意味から、構造式（２）の化合物中のポリエトキシユニ
ットの含有量は、極めて重要である。柔なんなエチレン
オキシドユニットは、親水性に富み且つ材料組成物中を
自由に動き易く、染色性を高度に達成させる事が出来
る。即ち、ポリエトキシユニットの含有量が多くなる
と、親水性が大きくなり染色性を向上させるためには、
有利である。が、ポリエトキシユニットの含有量が多く
なればなるほど共重合体の屈折率が低下するとともに、
柔なんとなり樹脂の耐熱性が低下する傾向となる。この
ため、本発明では、構造式（２）の化合物中のポリエト
キシユニットの含有量は、限定される。本発明では、ｎ
は、３から６の整数が用いられる。ｎの数が６を超える
と共重合体の屈折率が大幅に低下するとともに、柔なん
となり樹脂の耐熱性が低下する。一方ｎの数が３に満た
ないと、本発明の目的とする染色性に富む材料は得られ
ない。又、ｎの数が１から２の材料は、常温で固体また
は、粘調な液体であり、注型重合に適さない場合が多
い。この意味から本発明では、ｎは、３から６の整数が
好ましい範囲として用いられる。本発明の組成物は、こ
の様に、構造式（１）及び構造式（２）の単量体を必須
の成分として用いることにより、従来の眼鏡材料と比較
し、比較的屈折率が高く、又、分散染料を分散させた温
浴中で容易に染料が拡散し、比較的高い濃度まで、染色
が可能となる有用なプラスチック製の眼鏡材料とするこ
とが可能になる。The monomer of structural formula (2) used in the present invention is a monomer born from such a background. In the compound of the structural formula (2), it is necessary to increase the content of the bisphenol A type aromatic group, especially for the purpose of increasing the refractive index, and it is preferable that the content of the polyethoxy group is small. However, a resin obtained only from this compound is highly hydrophobic and does not easily serve as a material having a desired dyeability. From this meaning, the content of the polyethoxy unit in the compound of structural formula (2) is extremely important. The soft ethylene oxide unit is rich in hydrophilicity and can easily move freely in the material composition, and can highly achieve dyeability. That is, when the content of the polyethoxy unit is increased, the hydrophilicity is increased and the dyeability is improved.
It is advantageous. However, as the content of polyethoxy units increases, the refractive index of the copolymer decreases, and
It becomes soft and the heat resistance of the resin tends to decrease. Therefore, in the present invention, the content of polyethoxy units in the compound of structural formula (2) is limited. In the present invention, n
Is an integer from 3 to 6. When the number of n exceeds 6, the refractive index of the copolymer is significantly lowered, and the resin becomes soft and the heat resistance of the resin is lowered. On the other hand, if the number of n is less than 3, the material having excellent dyeing properties, which is the object of the present invention, cannot be obtained. Further, the material having the number of n of 1 to 2 is a solid or a viscous liquid at room temperature and is not suitable for cast polymerization in many cases. From this meaning, in the present invention, an integer of 3 to 6 is used as a preferable range for n. Thus, the composition of the present invention has a relatively high refractive index as compared with conventional eyeglass materials by using the monomers of structural formulas (1) and (2) as essential components, Further, the dye easily diffuses in the warm bath in which the disperse dye is dispersed, and it becomes possible to provide a useful plastic eyeglass material which enables dyeing to a relatively high concentration.
【００１０】本発明のモノマ−は、これら化合物（１）
及び（２）の他にこれら化合物（１）及び（２）と共重
合可能な単量体を共重合相手として用いることが出来
る。この共重合可能な単量体が用いられる意図は、共重
合体の重合速度を調節したり、モノマ−粘度をラジカル
キャスティング重合に適した粘度に調節したり、又、成
形性を調整したり、樹脂の屈折率を調整する等、種々の
目的のために使用される。具体的なこれら第３成分とし
ての単量体の例としては、メチルメタクリレ−ト、ブチ
ルメタクリレ−ト、フェニルメタクリレ−ト、イソブチ
ルメタクリレ−ト、等の各種メタクリルエステル、スチ
レン、クロルスチレン、ブロモスチレン、αーメチルス
チレン、ジビニルベンゼン等の各種ビニル化合物等であ
る。これらは、ほんの一例であり、本発明は、これらの
みに限定されない。The monomer of the present invention is the compound (1)
In addition to (2) and (2), monomers copolymerizable with these compounds (1) and (2) can be used as a copolymerization partner. The purpose of using this copolymerizable monomer is to adjust the polymerization rate of the copolymer, to adjust the monomer viscosity to a viscosity suitable for radical casting polymerization, or to adjust the moldability, It is used for various purposes such as adjusting the refractive index of the resin. Specific examples of the monomer as the third component include various methacrylic esters such as methyl methacrylate, butyl methacrylate, phenyl methacrylate, isobutyl methacrylate, styrene, and chloro. Various vinyl compounds such as styrene, bromostyrene, α-methylstyrene, divinylbenzene and the like. These are just examples and the present invention is not limited thereto.
【００１１】次に、本発明で用いられるモノマ−成分と
しての化合物（１）及び（２）、及び第３成分の割合
は、化合物（１）１０〜４０重量部、化合物（２）１０
〜３０重量部、第３成分３０〜８０重量部、が適当な範
囲として用いられる。化合物（１）の単量体が１０重量
部未満であると本発明の眼鏡材料組成物が充分高い屈折
率を得ることが出来ない。又、４０重量部を超えると比
較的高い屈折率を得ることが出来るが、染色性に欠ける
材料となる。次に、化合物（２）の使用が１０重量部未
満であると、疎水性が高く目的とする高度に染色性に富
む材料とならない。又、３０重量部を超えると、染色性
は向上するが共重合体の耐熱性は低下する。この意味か
ら本発明では、化合物（２）の単量体量は、１０〜３０
重量部が好ましい範囲として用いられる。Next, the ratio of the compounds (1) and (2) as the monomer component used in the present invention and the third component is 10 to 40 parts by weight of the compound (1) and the compound (2) 10.
˜30 parts by weight and the third component 30 to 80 parts by weight are used as appropriate ranges. When the amount of the compound (1) monomer is less than 10 parts by weight, the spectacle material composition of the present invention cannot obtain a sufficiently high refractive index. Further, when it exceeds 40 parts by weight, a relatively high refractive index can be obtained, but the material lacks dyeability. Next, if the amount of the compound (2) used is less than 10 parts by weight, the material will not be highly hydrophobic and will not be the desired highly dyeable material. If it exceeds 30 parts by weight, the dyeability is improved but the heat resistance of the copolymer is lowered. From this meaning, in the present invention, the amount of the compound (2) monomer is 10 to 30.
Parts by weight are used as a preferred range.
【００１２】又、第３成分のモノマ−は、その使用目的
によって３０〜５０重量部の範囲で使用することによ
り、良好な眼鏡材料組成物とすることが出来る。以上の
理由により、本発明の眼鏡材料のモノマ−原料は、化合
物（１）で示される単量体が１０〜４０重量部、化合物
（２）で示される単量体１０〜３０重量部、第３成分の
単量体３０〜８０重量部、が適当な組成として用いるこ
とが可能である。The monomer of the third component may be used in an amount of 30 to 50 parts by weight depending on the purpose of use, whereby a good spectacle material composition can be obtained. For the above reasons, the monomer raw material of the eyeglass material of the present invention contains 10 to 40 parts by weight of the monomer represented by the compound (1), 10 to 30 parts by weight of the monomer represented by the compound (2), and It is possible to use 30 to 80 parts by weight of the three-component monomer as an appropriate composition.
【００１３】次に、本発明の眼鏡材料組成物の具体的な
製造方法を述べる。前述した様に、本発明の樹脂は、ラ
ジカルキャスティング重合によって得られる。先ず、本
発明の範囲内の特定のモノマ−組成を混合し、更に、ラ
ジカル重合開始剤を添加して均一なモノマ−溶液を作製
する。このモノマ−溶液を硝子製、各種のプラスチック
製、または、金属製で出来た型（モ−ルド）の中に注入
し、室温もしくは、加温下にラジカル重合を開始させ、
目的とする形状に成形された眼鏡材料を得ることが出来
る。Next, a specific method for producing the eyeglass material composition of the present invention will be described. As mentioned above, the resin of the present invention is obtained by radical casting polymerization. First, a specific monomer composition within the scope of the present invention is mixed, and a radical polymerization initiator is further added to prepare a uniform monomer solution. This monomer solution is poured into a mold (mold) made of glass, various plastics, or metal, and radical polymerization is started at room temperature or under heating,
It is possible to obtain a spectacle material molded into a desired shape.
【００１４】ラジカル重合開始剤は、特に限定はなく通
常、ラジカル重合に用いられる開始剤を使用することが
出来る。又、重合温度は、室温から１２０℃程度の範囲
の温度が一般に使用される。この様にして得られた成形
物は、そのまま眼鏡レンズとして使用することもできる
が、用途によって切削、研磨などの手段を施して各種の
眼鏡材料とすることも可能である。又、染色、ハ−ドコ
−ト、反射防止コ−ト等を施すことも有力な手段であ
る。この様にして得られた本発明の樹脂組成物は、従来
の硝子製やプラスチックの眼鏡材料と比べ比較的屈折率
が高く、又、極めて染色性に優れた眼鏡材料組成物を提
供するものである。次に、実施例で更に、説明を加え
る。The radical polymerization initiator is not particularly limited, and an initiator usually used for radical polymerization can be used. The polymerization temperature is generally in the range of room temperature to 120 ° C. The molded product thus obtained can be used as it is as a spectacle lens, but can also be processed into various spectacle materials by subjecting it to means such as cutting and polishing depending on the intended use. Further, dyeing, hard coating, anti-reflection coating and the like are also effective means. The resin composition of the present invention thus obtained provides a spectacle material composition having a relatively high refractive index as compared with conventional glass or plastic spectacle materials, and having extremely excellent dyeability. is there. Next, further description will be given in the examples.
【００１５】[0015]
実施例（１） ４，４’ーチオビスベンゼンチオ−ルジメタクリレ−ト ２０重量部 下記化５〔構造式（３）〕で示される 2,2'- ヒ゛ス［4-（メタクリロキシ・ホ゜リエトキシ）フェニル］フ゜ロハ゜ン １２重量部 Example (1) 4,4′-thiobisbenzenethiol dimethacrylate 20 parts by weight 2,2′-bis [4- (methacryloxypolyethoxy) phenyl] represented by the following chemical formula 5 [structural formula (3)] Propan 12 parts by weight
【００１６】[0016]
【化５】 [Chemical 5]
【００１７】 2,2'- ヒ゛ス［4-（メタクリロキシ・シ゛エトキシ ）フェニル］フ゜ロハ゜ン ４０重量部 αーメチルスチレン ２８重量部 を良く混合し、これに、更に、ラウロイルパ−オキサイ
ド１．５重量部を室温で溶解させ、モノマ−溶液とし
た。これを、ガスケットで固定された硝子製モ−ルドの
間に注入し、次の条件で重合を行った。 ５０℃ １６時間 ７０℃ ４時間 ９０℃ ２時間 重合後の成形体は、厚み１．５ｍｍ、ジオプタ−０．２
５であった。又、無色透明で、可視光線透過率は、９０
％を示した。（可視光線透過率の測定は、ＡＳＴＭ Ｄ
１００３ー５２の方法に準じた。）又、この材料の屈折
率は、１．５９２と比較的高い値を示した。次に、この
成形体の染色性をテストした。テスト方法は、０．２％
の水分散性染料ディスパ−ジョンブラウン３水溶液を９
２℃に昇温し、この水溶液中に成形体を１０分間浸漬さ
せ、取り出した後良く水洗後、可視光線透過率を求める
ことにより染色性試験とした。実施例（１）の成形体の
染色テスト後の可視光線透過率は、５６％を示し極めて
染色性に富むことが確認された。2,2′-Vise [4- (methacryloxy-diethoxy) phenyl] propoline 40 parts by weight α-methylstyrene 28 parts by weight were mixed well, and further, 1.5 parts by weight of lauroyl peroxide was dissolved therein. To obtain a monomer solution. This was injected into a glass mold fixed with a gasket, and polymerization was performed under the following conditions. 50 ° C. 16 hours 70 ° C. 4 hours 90 ° C. 2 hours The molded body after polymerization has a thickness of 1.5 mm and diopter-0.2.
It was 5. It is colorless and transparent and has a visible light transmittance of 90.
%showed that. (Visible light transmittance is measured by ASTM D
According to the method of 1003-52. ) Further, the refractive index of this material was 1.592, which was a relatively high value. Next, the dyeability of this molded article was tested. The test method is 0.2%
Of water dispersible dye Dispersion Brown 3 aqueous solution of 9
The temperature was raised to 2 ° C., the molded article was dipped in this aqueous solution for 10 minutes, taken out, thoroughly washed with water, and then the visible light transmittance was determined to obtain a dyeability test. The visible light transmittance of the molded product of Example (1) after the dyeing test was 56%, and it was confirmed that the molded product had an extremely high dyeability.
【００１８】比較例（１） 実施例（１）で使用した ４，４’ーチオビスベンゼンチオ−ルジメタクリレ−ト ２０重量部 2,2'- ヒ゛ス［4-（メタクリロキシ・シ゛エトキシ ）フェニル］フ゜ロハ゜ン ５２重量部 α- メチルスチレン ２８重量部 を良く混合し、実施例（１）と同じ条件で重合を行いジ
オプタ−０．２５の凹レンズを得た。無色透明で、可視
光線透過率は、９０％を示した。又、この材料の屈折率
は、１．５９３と比較的高い値を示した。しかし、比較
例（１）の成形体の染色テスト後の可視光線透過率は、
８４％を示し染色性に極めて難が有ることが認められ
た。この様に構造式（２）で示されるジメタクリルエス
テルのエチレノキシドユニットのｎの数が５の材料を用
いることにより、染色性が向上することが示された。Comparative Example (1) 4,4'-thiobisbenzenethiol dimethacrylate used in Example (1) 20 parts by weight 2,2'-bis [4- (methacryloxy-diethoxy) phenyl] fluorene 52 By weight 28 parts by weight of α-methylstyrene was mixed well, and polymerization was carried out under the same conditions as in Example (1) to obtain a diopter-0.25 concave lens. It was colorless and transparent and had a visible light transmittance of 90%. The refractive index of this material was 1.593, which was a relatively high value. However, the visible light transmittance of the molded article of Comparative Example (1) after the dyeing test was
It was 84% and it was recognized that the dyeability was extremely difficult. As described above, it was shown that the dyeability is improved by using the material in which the number n of the ethylenoxide unit of the dimethacrylic ester represented by the structural formula (2) is 5.
【００１９】実施例（２） ４，４’ーチオビスベンゼンチオ−ルジメタクリレ−ト ３０重量部 下記化６〔構造式（４）〕で示される 2,2'- ヒ゛ス［4-（アクリロキシ・ホ゜リエトキシ ）フェニル］フ゜ロハ゜ン ２５重量部Example (2) 4,4'-thiobisbenzenethiol dimethacrylate 30 parts by weight 2,2'-bis [4- (acryloxypolyethoxy) represented by the following chemical formula 6 [structural formula (4)] ) Phenyl] Fluorine 25 parts by weight
【００２０】[0020]
【化６】 [Chemical 6]
【００２１】 2,2'-ヒ゛ス ［4-（メタクリロキシ・シ゛エトキシ ）フェニル］フ゜ロハ゜ン ２５重量部 α- メチルスチレン １０重量部 ジビニルベンゼン（５６％） １０重量部 を良く混合し、これに、 更に、ラウロイルパ−オキサ
イド１．５重量部を室温で溶解させ、モノマ−溶液とし
た。これを、ガスケットで固定された硝子製モ−ルドの
間に注入し、実施例（１）と同じ条件で重合を行い、厚
み１．５ｍｍ、ジオプタ−０．２５のレンズを得た。
又、この材料は、無色透明で、可視光線透過率は、９０
％を示した。又、この材料の屈折率は、１．５９６と比
較的高い値を示した。実施例（１）に準ずる方法で行わ
れた染色テスト後の可視光線透過率は、３２％を示しき
わめて染色性に富むことが確認された。2,2'-Vise [4- (methacryloxy-diethoxy) phenyl] fluorene 25 parts by weight α-methylstyrene 10 parts by weight Divinylbenzene (56%) 10 parts by weight were mixed well, and further lauroylperoxide was added. -1.5 parts by weight of oxide was dissolved at room temperature to obtain a monomer solution. This was injected into a glass mold fixed with a gasket, and polymerization was performed under the same conditions as in Example (1) to obtain a lens having a thickness of 1.5 mm and diopter-0.25.
This material is colorless and transparent, and has a visible light transmittance of 90.
%showed that. The refractive index of this material was 1.596, which was a relatively high value. It was confirmed that the visible light transmittance after the dyeing test carried out by the method according to Example (1) was 32%, which was extremely rich in dyeability.
【００２１】[0021]
【発明の効果】本発明の眼鏡レンズ材料樹脂組成物は、
従来の眼鏡材料と比較し、比較的屈折率が高く、又、分
散染料を分散させた温浴中で容易に染料が拡散し、比較
的高い濃度まで、染色が可能となる有用なプラスチック
製の眼鏡材料組成物を提供するものである。The spectacle lens material resin composition of the present invention is
Useful plastic eyeglasses that have a relatively high refractive index compared to conventional eyeglass materials, and that the dye easily diffuses in a warm bath in which a disperse dye is dispersed, allowing dyeing to a relatively high concentration. A material composition is provided.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｇ０２Ｃ 7/02 ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI technical display location G02C 7/02
Claims (1)
４，４’ーチオビスベンゼンチオ−ルジメタクリレ−ト
単量体１０〜４０重量部、下記化２〔構造式（２）〕で
示される２官能性単量体１０〜３０重量部、及びこれら
と共重合可能な単量体３０〜８０重量部、とをラジカル
キャスト重合成形することに依って得られる染色性に富
む屈折率１．５８以上の高屈折率樹脂組成物 【化１】 【化２】 1. 10 to 40 parts by weight of a 4,4′-thiobisbenzenethiol dimethacrylate monomer represented by the following chemical formula 1 [structural formula (1)], and the following chemical formula 2 [structural formula (2)] 10 to 30 parts by weight of a bifunctional monomer represented by and 30 to 80 parts by weight of a monomer copolymerizable therewith, and a refractive index having a high dyeing property obtained by radical casting polymerization molding. High refractive index resin composition of 1.58 or more [Chemical 2]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18341893A JP3418427B2 (en) | 1993-06-30 | 1993-06-30 | Resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18341893A JP3418427B2 (en) | 1993-06-30 | 1993-06-30 | Resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0718041A true JPH0718041A (en) | 1995-01-20 |
| JP3418427B2 JP3418427B2 (en) | 2003-06-23 |
Family
ID=16135436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18341893A Expired - Fee Related JP3418427B2 (en) | 1993-06-30 | 1993-06-30 | Resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3418427B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997019964A1 (en) * | 1995-11-27 | 1997-06-05 | Sumitomo Seika Chemicals Co., Ltd. | Curable resin compositions |
| US6953623B2 (en) | 2000-12-21 | 2005-10-11 | 3M Innovative Properties Company | Optical product having a high refractive index microreplication resin |
-
1993
- 1993-06-30 JP JP18341893A patent/JP3418427B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997019964A1 (en) * | 1995-11-27 | 1997-06-05 | Sumitomo Seika Chemicals Co., Ltd. | Curable resin compositions |
| US6953623B2 (en) | 2000-12-21 | 2005-10-11 | 3M Innovative Properties Company | Optical product having a high refractive index microreplication resin |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3418427B2 (en) | 2003-06-23 |
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