JPS58137801A - Anti-fogging plastic lens - Google Patents
Anti-fogging plastic lensInfo
- Publication number
- JPS58137801A JPS58137801A JP57020355A JP2035582A JPS58137801A JP S58137801 A JPS58137801 A JP S58137801A JP 57020355 A JP57020355 A JP 57020355A JP 2035582 A JP2035582 A JP 2035582A JP S58137801 A JPS58137801 A JP S58137801A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acrylate
- surface hardness
- resin
- lens
- 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
- 229920003023 plastic Polymers 0.000 title claims abstract description 9
- 239000004033 plastic Substances 0.000 title claims abstract description 9
- 229920005989 resin Polymers 0.000 claims abstract description 27
- 239000011347 resin Substances 0.000 claims abstract description 27
- 239000004094 surface-active agent Substances 0.000 claims abstract description 16
- 239000011247 coating layer Substances 0.000 claims abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 7
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract description 4
- 229920000728 polyester Polymers 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 3
- 229920001187 thermosetting polymer Polymers 0.000 abstract description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 3
- 239000004014 plasticizer Substances 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- -1 fluororesin Polymers 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 229920000180 alkyd Polymers 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- IISHLYLZTYTIJJ-UHFFFAOYSA-N 1-hydroxyethyl 2-methylprop-2-enoate Chemical compound CC(O)OC(=O)C(C)=C IISHLYLZTYTIJJ-UHFFFAOYSA-N 0.000 description 1
- UXYMHGCNVRUGNO-UHFFFAOYSA-N 1-hydroxypropan-2-yl prop-2-enoate Chemical compound OCC(C)OC(=O)C=C UXYMHGCNVRUGNO-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- OELQSSWXRGADDE-UHFFFAOYSA-N 2-methylprop-2-eneperoxoic acid Chemical class CC(=C)C(=O)OO OELQSSWXRGADDE-UHFFFAOYSA-N 0.000 description 1
- RYCHOYFETYRVLW-UHFFFAOYSA-N 3,3-dihydroxy-2-methylprop-2-enoic acid Chemical class OC(O)=C(C)C(O)=O RYCHOYFETYRVLW-UHFFFAOYSA-N 0.000 description 1
- WWSNKXVETXETTP-UHFFFAOYSA-N 3,3-dihydroxyprop-2-enoic acid Chemical class OC(O)=CC(O)=O WWSNKXVETXETTP-UHFFFAOYSA-N 0.000 description 1
- RMCLKZFGXBSDIO-UHFFFAOYSA-N 3,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(O)O RMCLKZFGXBSDIO-UHFFFAOYSA-N 0.000 description 1
- BXBBQMFWCACOBG-UHFFFAOYSA-N 3,3-dihydroxypropyl prop-2-enoate Chemical compound OC(O)CCOC(=O)C=C BXBBQMFWCACOBG-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- 244000007835 Cyamopsis tetragonoloba Species 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- BJSBGAIKEORPFG-UHFFFAOYSA-N [[6-amino-1,2,3,4-tetramethoxy-4-(methoxyamino)-1,3,5-triazin-2-yl]-methoxyamino]methanol Chemical compound CONC1(N(C(N(C(=N1)N)OC)(N(CO)OC)OC)OC)OC BJSBGAIKEORPFG-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical class OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/18—Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Surface Treatment Of Optical Elements (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は吸湿性を有し、かつ、表面硬度の優れた防曇性
プラスチックレンズに関するものである。詳しく述べる
と、吸湿性樹脂からなるレンズ基盤に界面活性剤を配合
した有機のハードコート層を設けた防曇性プラスチック
レンズに関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an antifogging plastic lens that is hygroscopic and has excellent surface hardness. More specifically, the present invention relates to an anti-fog plastic lens in which an organic hard coat layer containing a surfactant is provided on a lens base made of a hygroscopic resin.
従来のプラスチックレンズは、無機ガラスレンズに比べ
働り度合が小さいという特徴はあるが、それでも気温の
急激な変化をおこす環境では僑りてしまうという欠点が
ある。特に眼鏡用レンズにおいては、人が携帯し、かつ
、視力矯正用という極めて重要な医療用品であることか
ら、眼鏡を使用している人たちの間では、食事をしたり
冬季においてパスや電車に乗った時に曇らないレン〆の
要求が多い。このため防曇に係る技術の歴史もかなり古
いものがある。Conventional plastic lenses have the characteristic that they work less effectively than inorganic glass lenses, but they still have the disadvantage of becoming stale in environments where there are rapid changes in temperature. Eyeglass lenses in particular are an extremely important medical product that people carry with them and are used for vision correction. There are many requests for a finish that does not fog up when riding. For this reason, the history of anti-fogging technology is quite old.
゛ レンズ等の透明体の防曇レンズに関する先行技術と
しては古いものでは、特公昭３８−１６０２０号、特公
昭５’；ｌ−２１１１２号等であり、新しいものとして
は、特開昭５５−１１８２８５号。゛ Older prior art related to anti-fog lenses for transparent objects such as lenses include Japanese Patent Publication No. 38-16020 and Japanese Patent Publication No. 1-21112, and newer ones include Japanese Patent Publication No. 118285-1985. issue.
特開昭５３−１４６９８５号、特開昭５４−３５１８７
号、特開昭５４−７４２９１号等数多くの技−術、的開
発がなされている。JP-A-53-146985, JP-A-54-35187
Numerous technologies and developments have been made, such as in Japanese Patent Application Laid-Open No. 54-74291.
レンズの曇り防止対策としては １、 水との表面接触角を小さくする。To prevent lens fogging, 1. Reduce the surface contact angle with water.
２ 表面に析出した水を吸収する。2. Absorbs water deposited on the surface.
＆ 水滴が表面につかないように撥水性をもたせる。& Provide water repellency to prevent water droplets from adhering to the surface.
の５方法が考えられる。１は界面活性剤で実現できる。There are five possible methods. 1 can be achieved with a surfactant.
２は吸湿性樹脂、例えばポリビニルアルコールの如き親
水性官能基を有するポリマーを塗布することで実現が可
能である。３については弗素樹脂、シリコン樹脂、油等
の撥水性樹脂を塗布すればよいが、Ｉ！鏡用レンズへの
応用は、程んど実現されていない。３に非常に似た技術
として、レンズの表面温度を高めて、結露させない方法
も航空機関係で発熱抵抗体として、透明電導性被膜（一
般的にはネサ膜と呼ばれる）を形成し、環境条件を意識
的に変化させる方法が実現されてきた。2 can be realized by applying a hygroscopic resin, for example a polymer having a hydrophilic functional group such as polyvinyl alcohol. Regarding 3, you can apply a water-repellent resin such as fluororesin, silicone resin, or oil, but I! Application to mirror lenses has not yet been realized. A technique very similar to 3 is to raise the surface temperature of the lens to prevent dew condensation, which is used in aircraft-related applications to form a transparent conductive film (generally called a NESA film) as a heating resistor to control environmental conditions. Methods for conscious change have been realized.
しかしながら上記１については、防曇性能の持続性がな
い。２については、耐水性や傷がつき易い負
などから実用には至っていない。近年２の方法によるも
のであるが、吸湿性樹脂に、エポキシ、メラミン、シリ
コン樹脂等の、硬度的にちりあるいは耐光性にも優れた
熱硬化性樹脂を同時にコーティングし、さらには界面活
性剤を含浸させたコート層を有した眼鏡レンズが発売さ
れるに至っているが、界面活性剤がぬけてしまう、耐水
性に劣る、耐擦傷性が十分でないなどの欠点を有してい
る。However, regarding item 1 above, the antifogging performance is not sustainable. Regarding No. 2, it has not been put into practical use due to its water resistance and the fact that it is easily scratched. In recent years, method 2 has been used, but hygroscopic resins are simultaneously coated with thermosetting resins that have excellent hardness and dust and light resistance, such as epoxy, melamine, and silicone resins, and are also coated with surfactants. Eyeglass lenses with impregnated coating layers have come on the market, but they have drawbacks such as the surfactant coming off, poor water resistance, and insufficient scratch resistance.
特公昭５２−２２６４４号では、レンズ基盤の上にポリ
ビニルアルコール等の吸湿性樹脂を塗布し、さらにその
上に界面活性剤を配合したメラミン系等の有機のハード
コート層を設けることにより、表面硬度の向上と、防曇
効果の両方を兼備えたものがある。この方法によれば、
吸湿性樹脂膜の上に設けられた有機のハードコート層に
よって表面の硬度が向上し、又、吸湿性樹脂層と、有機
のハードコート層中に含まれる界面活性剤によって、あ
る程度の防曇効果も得られる。しかし、多量の水分が飛
来した場合においては、レンズ表面に水滴となって現わ
れる。すなわち、少量の水分であれば吸収できるが、多
量の水分が飛来した場合においては、吸湿性樹脂層が薄
いため、吸湿性樹脂層が水分によって飽和状態となり、
防曇効果は全くなくなってしまう。In Japanese Patent Publication No. 52-22644, surface hardness is improved by coating a hygroscopic resin such as polyvinyl alcohol on the lens base and further providing an organic hard coat layer such as melamine-based hard coat layer containing a surfactant. There are some products that have both an improvement in fog and an anti-fog effect. According to this method,
The organic hard coat layer provided on the hygroscopic resin film improves the surface hardness, and the hygroscopic resin layer and the surfactant contained in the organic hard coat layer provide a certain degree of anti-fogging effect. You can also get However, when a large amount of water comes flying into the lens, it appears as water droplets on the lens surface. In other words, a small amount of water can be absorbed, but if a large amount of water comes flying in, the hygroscopic resin layer becomes saturated with water because the hygroscopic resin layer is thin.
The anti-fog effect is completely lost.
本発明は上記の欠点を除去したもので、吸湿性樹脂から
なるレンズ基盤の上に、界面活性剤を配合した有機のハ
ードコート層を設けた防曇性プラスチックレンズに関す
る。The present invention eliminates the above drawbacks and relates to an antifogging plastic lens in which an organic hard coat layer containing a surfactant is provided on a lens base made of a hygroscopic resin.
以下、図面を用いて本発明の詳細な説明する。Hereinafter, the present invention will be explained in detail using the drawings.
第１図は、表面硬度が充分に高くかつ防曇性能に極めて
優れた防曇性プラスチックレンズの断面図である。基盤
１は、親水性アクリ□レートやメタクリレート重合体等
の吸湿性樹脂、２は界面活性剤を含んだ有機のハードコ
ート層を示す、１の吸湿性樹脂は、その吸水容量が非常
に大きい為、多量の水分が飛来した場合にも防曇効果が
低下することはない。しかし、この種の樹脂は表面硬度
が充分であるとはいい難く、特に水分によって膨潤した
場合においては、ハンカチ等で軽く拭いた程度で優がつ
いてしまう。そのため基盤１の上にメラミン系、シリコ
ン系−エボキシ系、アクリル系。FIG. 1 is a cross-sectional view of an anti-fog plastic lens that has sufficiently high surface hardness and extremely excellent anti-fog performance. Base 1 is a hygroscopic resin such as hydrophilic acrylate or methacrylate polymer, 2 is an organic hard coat layer containing a surfactant, and the hygroscopic resin 1 has a very large water absorption capacity. The anti-fogging effect does not deteriorate even when a large amount of water is blown into the product. However, this type of resin cannot be said to have sufficient surface hardness, and especially when it is swollen by moisture, the surface hardness becomes poor even when gently wiped with a handkerchief or the like. Therefore, melamine, silicone-epoxy, and acrylic are used on the base 1.
グアナミン系、尿素系、アルキッド系、アクリル−アル
キッド系、ポリエステル系等の有機のハードコート層を
設けることにより表面硬度を向上部せることができる。The surface hardness can be improved by providing an organic hard coat layer of guanamine type, urea type, alkyd type, acrylic-alkyd type, polyester type, etc.
しかしながら、優れた防曇効果をもつ基盤１が、防曇効
果を全くもたない有機のハードコート膜によっておおわ
れてしまうためにその防曇効果は全く失われてしまう。However, since the substrate 1, which has an excellent antifogging effect, is covered with an organic hard coat film having no antifogging effect, the antifogging effect is completely lost.
有機のハードコート液中に界面活性剤を添加し塗布する
ことにより、ハードコート層中に分散した界面活性剤が
レンズ表面と基盤１とのパイプ役をなす。よって、レン
ズ表面に飛来した水分は瞬時にかつ円滑に基盤１に送り
込まれ、極めて優れた防曇効果が得られる。従来、防曇
効果と表面硬度とは背反するものであったがＪこの方法
によれば有機のハードコート層により−れた表面硬度を
保ちながら、かつ、基盤の吸湿性樹脂と、Ｆ機ノ−−ド
コート層中に含まれる界面活性剤のはたらきによって、
極めて優れた防曇効果が得られる。このように本発明は
、両者の特徴ある性能をそれぞれ充分に発揮させること
により成功した表面硬度の優れた防曇性プラスチックレ
ンズである。By adding and applying a surfactant to the organic hard coat liquid, the surfactant dispersed in the hard coat layer acts as a pipe between the lens surface and the base 1. Therefore, the moisture flying onto the lens surface is instantly and smoothly sent to the base 1, and an extremely excellent anti-fogging effect can be obtained. Conventionally, the antifogging effect and surface hardness were contradictory, but with this method, while maintaining the surface hardness provided by the organic hard coat layer, the hygroscopic resin of the base --Due to the action of the surfactant contained in the docoat layer,
An extremely excellent anti-fog effect can be obtained. As described above, the present invention is an anti-fog plastic lens with excellent surface hardness that has been successfully achieved by fully demonstrating the characteristic performances of both.
本発明に用いられる吸湿性樹脂は、次に述べるα）＊ｈ
）ｅ’）の単量体°を所定の割合で共重合させることに
より得られる。The hygroscopic resin used in the present invention is α)*h described below.
) can be obtained by copolymerizing the monomers of e') in a predetermined ratio.
α） １以上のアルコール性水酸基を有する（メタ）ア
クリル酸エステル類 ２０〜８０重量部
ｂ） 多官能性（メタ）アクリル酸エステル類２０〜８
０重量部
ｅ） （メタ）アクリル酸エステル類（しかしα）と
ｂ）を除く） ０〜６０重量部
本発明に用いられる１以上のアルコール性水酸基を有す
る（メタ）アクリル酸エステル類としては、２−とドロ
キシエチルアクリレート、２−ヒドロキシプロピルアク
リレート、１−メチル−２−ヒドロキシエチルアクリレ
ート等のモノヒドロキシアクリレート類、２−とドロキ
シエチルメタクリレート、２−ヒドロキシプロピルメタ
クリレート等のモノヒドロキシメタクリレート類、２゜
３ジヒドロキシプロピルアクリレート、２．３ジヒドロ
キシプロピルメタクリレート等のジヒドロキシアクリレ
ート類及びジヒドロキシメタクリレート類郷を挙げるこ
とができる。上記（メタ）アクリル酸エステル類のうち
ジヒドロキシメタクリレート類が防曇性能において特に
すぐれた効果を発揮する。α) (Meth)acrylic esters having one or more alcoholic hydroxyl groups 20 to 80 parts by weightb) Polyfunctional (meth)acrylic esters 20 to 8
0 parts by weight e) (meth)acrylic esters (but excluding α) and b)) 0 to 60 parts by weight The (meth)acrylic esters having one or more alcoholic hydroxyl groups used in the present invention include: 2- and monohydroxy acrylates such as droxyethyl acrylate, 2-hydroxypropyl acrylate, and 1-methyl-2-hydroxyethyl acrylate; 2- and monohydroxy methacrylates such as 2-hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate; Mention may be made of dihydroxyacrylates and dihydroxymethacrylates such as 2.3 dihydroxypropyl acrylate and 2.3 dihydroxypropyl methacrylate. Among the above (meth)acrylic acid esters, dihydroxy methacrylates exhibit particularly excellent antifogging properties.
本発明に用いられる多官能性（メタ）アクリル酸エステ
ル類としては、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、
トリエチレングリコールジ（メタ）アクリレート、ｌリ
エチレングリコールジ（メタ）アクリレート、ネオペン
チルグリコールジ（メタ）アクリレート、ジプロピレン
グリコールジ（メタ）アクリレート、ポリアルキレング
リコールジ（メタ）アクリレート、、１．６−ヘキサン
ゲリコールジ（メタ）アクリレート等のジ（メタ）アク
リレート類、トリメチロールプロパントリ（メタ）アク
リレート、トリメチロールエタン／トリ（メタ）アクリ
レート等のトリ（メタ）アクリレート類、テトラメチロ
ールメタンテトラ（メタ）アクリレート等のテ、トラ（
メタ）アクリレート類等である。The polyfunctional (meth)acrylic acid esters used in the present invention include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate,
Triethylene glycol di(meth)acrylate, l-lyethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, polyalkylene glycol di(meth)acrylate, 1.6- Di(meth)acrylates such as hexane gelicoldi(meth)acrylate, tri(meth)acrylates such as trimethylolpropane tri(meth)acrylate, trimethylolethane/tri(meth)acrylate, tetramethylolmethanetetra(meth)acrylate, etc. ) acrylate etc. Te, Tora (
meth)acrylates, etc.
また、本発明で用いられる単量体Ｃ）は通常使用されて
いる（メタ）アクリル酸エステル類であればなんでもよ
いが、メチル（メタ）アクリレート、エチル（メタ）ア
クリレート、プロピル（メタ）アクリレート、イソでロ
ピル（メタ）アクリレート、露−ブチル（メタ）アクリ
レート、ｌ５Ｏ−ブチル（メタ）アクリレート、ｔ−ブ
チル（メタ）アクリレート、ネオペンチル（メタ）アク
リレージ等のアルキル化（メタ）アクリレート類、シク
ロヘキシル（メタ）アクリレート等の脂環式アルキル化
（メタ）アクリレート類、２−クロロエチル（メタ）ア
クリレート等のハロゲン化アルキル（メタ）アクリレー
ト類、エチレングリコールモノ（メタ）アクリレート、
１ジエチレングリコールモノ（メタ）アクリレート、ト
リエチレノ
ングリコールモノ（メタ）７クリレート等のポリエチレ
ングリコールモノ（メタ）アクリレート類等が特に好ま
しい。Furthermore, the monomer C) used in the present invention may be any commonly used (meth)acrylic ester, including methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, Alkylated (meth)acrylates such as iso-propyl (meth)acrylate, dew-butyl (meth)acrylate, l5O-butyl (meth)acrylate, t-butyl (meth)acrylate, neopentyl (meth)acrylate, cyclohexyl (meth)acrylate, etc. ) alicyclic alkylated (meth)acrylates such as acrylate, halogenated alkyl (meth)acrylates such as 2-chloroethyl (meth)acrylate, ethylene glycol mono(meth)acrylate,
Particularly preferred are polyethylene glycol mono(meth)acrylates such as 1-diethylene glycol mono(meth)acrylate and triethylene glycol mono(meth)7-acrylate.
一方、本発明に用いられる表面硬度の充分に高い樹脂と
しては、シリコン系、メラミン系、グア。On the other hand, examples of resins with sufficiently high surface hardness used in the present invention include silicone-based, melamine-based, and guar.
ナ之ン系、尿素系、エポキシ系、アクリル系、アルキッ
ド系、アクリル−アルキッド系、ポリエステル系等の熱
硬化性樹脂が有効である。Thermosetting resins such as nano, urea, epoxy, acrylic, alkyd, acrylic-alkyd, and polyester are effective.
また、水分子の界面活性剤による輸送現象をより容易に
するために、可塑剤等を反応させ、被膜内に自由空間を
発生しやすくすることも有効である。Furthermore, in order to facilitate the transport phenomenon of water molecules by the surfactant, it is also effective to react with a plasticizer or the like to facilitate the generation of free space within the film.
本発明において押いられる前記表面硬度の高い樹脂中に
配合される界面活性剤としては、ポリオキシアルキレン
エーテル、脂肪族のポリオキシエチレングリコールエー
テル、ポリオキシエチレンアルキル′フェノールエーテ
ル、ポリアルキレングリコ−λ、ポリオキシア、ルキレ
ンアルキルアミン、ポリオキシアルキレンアルキルアミ
ド、アルキルメチルタウライドなどが特に好ましい。The surfactants to be blended into the resin with high surface hardness to be pressed in the present invention include polyoxyalkylene ether, aliphatic polyoxyethylene glycol ether, polyoxyethylene alkyl'phenol ether, polyalkylene glyco-λ , polyoxia, alkylenealkylamine, polyoxyalkylenealkylamide, alkylmethyltauride, and the like are particularly preferred.
以下実施例に基づいて本発明の詳細な説明する実施例−
１
２−とドロキシエチルメタクリレート６０重量ｌ！、エ
チレングリコールジメタクリレート４０重量部、ｔ−ブ
チルパーオキ、シネオデヵノエート（日本油脂製、パー
ブチルＮＤ）（１５重量部からなる単量体混合物を、２
枚のガラス型とガスケットで組み立てられたレンズ型に
注入し、２５℃カラ８０℃まで直線的に２日間かけて上
昇させた後、８０℃で５時間保持し、１日かけて室温ま
でもしした。このようにして出来上がりたレンズに、ヘ
キサメトキシメチロールメラミンとポリエチレングリコ
ールとの共重合体にポリオキシエチレンアルキルエーテ
ルな前記共重合体に対して１０重量部添加したものをデ
ィッピングによりコーティングし、１００℃中で２時間
硬化した。出来上がったレンズに息をふきかけたが曇ら
ず、１時間煮沸させた後に同様の試験をしたが防曇性能
に変化はみられなかった。又、耐擦傷性試験として、５
Ｏ０００スチールウールで強く摩擦しても優がつかなか
った。その他、耐薬品性、耐光性、制電性等の試験に対
しても著しい向上がみられた。EXAMPLES The present invention will be explained in detail based on the following examples.
1 2- and 60 liters of droxyethyl methacrylate! , 40 parts by weight of ethylene glycol dimethacrylate, t-butyl peroxide, and cineodecanoate (Perbutyl ND manufactured by NOF Co., Ltd.) (15 parts by weight).
It was injected into a lens mold assembled with a glass mold and a gasket, and the temperature was raised linearly from 25°C to 80°C over 2 days, then held at 80°C for 5 hours, and then warmed to room temperature over 1 day. . The lens thus obtained was coated with a copolymer of hexamethoxymethylolmelamine and polyethylene glycol in which 10 parts by weight of the copolymer of polyoxyethylene alkyl ether was added by dipping at 100°C. It was cured for 2 hours. When I blew on the finished lens, it did not fog up, and after boiling it for an hour, I conducted a similar test and found no change in anti-fog performance. In addition, as a scratch resistance test, 5
Even if I rubbed it strongly with O000 steel wool, it did not get better. In addition, significant improvements were seen in tests such as chemical resistance, light resistance, and antistatic properties.
実施例−２
２−ヒドロキシプロピルメタクリレート８０重量部、エ
チレングリコールジメタクリレート２゜−置部、ｔ−ブ
チルパーオキシビパレート（日本油脂製、パーブチルＰ
Ｕ）１１５重量部からなる単量体混合物を実施例−１と
同じ条件で硬化した。Example-2 80 parts by weight of 2-hydroxypropyl methacrylate, 2 parts of ethylene glycol dimethacrylate, t-butyl peroxybiparate (Nippon Oil Co., Ltd., Perbutyl P)
U) A monomer mixture consisting of 115 parts by weight was cured under the same conditions as in Example-1.
次にテトラエトキシシラン４０重量部、ｒ−グリシドオ
キシプロビルトリメトキシシラン２０重量部を、イソプ
ロピルアルコール４０重量部に溶解し、さらにα０．５
規定塩酸水溶液１０重量部を加え、８０℃で４時間還流
攪拌し、その後、室温にもどしてから９ ｎ ＯＡＨを
０．２（ｆ）とポリオキシエチレンアルキルエーテルを
１０重量部添加シて充１分に攪拌した液を、前記で得た
レンズにディッピングによりコーティングした後、１３
０℃中で２時間硬化した。結果は実施例−１同様良好で
あった。Next, 40 parts by weight of tetraethoxysilane and 20 parts by weight of r-glycidoxyprobyltrimethoxysilane were dissolved in 40 parts by weight of isopropyl alcohol, and further α0.5
Add 10 parts by weight of a normal aqueous hydrochloric acid solution, stir under reflux at 80°C for 4 hours, then return to room temperature and add 0.2 (f) of 9N OAH and 10 parts by weight of polyoxyethylene alkyl ether to fill the mixture. After coating the lens obtained above with the solution stirred for 13 minutes,
It was cured for 2 hours at 0°C. The results were good as in Example-1.
実施例−３
１−ヒドロキシエチルメタクリレート６０重量部、エチ
レングリコールジメタクリレート３０重量部、メトキシ
ポリエチレングリコール４００メタクリレート（新中村
化学製）１０重量部、ジイソプロピルパーオキシジカー
ボネート（日本油脂商品名、工ＰＰ）（１５重量部から
なる単量体混合物を１５℃で４日間保温した以外は実施
例−１と同様の方法で重合させた。次にテトラメトキシ
シラン１０重量部、およびｒ−グリシドオキシプロビル
トリメトキシシラン５０重量部をイソプロピルアルコー
ル４０重量部に溶解し、さらにα０５規定塩醗水溶液１
０重量部を加え、室温で８時間攪拌したのち、Ｓ鴇ｏｚ
！を（Ｌ２ （ｆ）と、ポリオキシアルキレンエーテル
を１０重量部添加し、充分に攪拌した液を、前記で得ら
れたレンズにディッピングによりてコーティングし、１
３０℃中で２時間硬化させた。結果は実施例−１と同様
良好でありた。Example-3 60 parts by weight of 1-hydroxyethyl methacrylate, 30 parts by weight of ethylene glycol dimethacrylate, 10 parts by weight of methoxypolyethylene glycol 400 methacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.), diisopropyl peroxydicarbonate (product name of Nippon Oil & Fats Co., Ltd., Ko-PP) (Polymerization was carried out in the same manner as in Example 1 except that the monomer mixture consisting of 15 parts by weight was kept at 15°C for 4 days. Next, 10 parts by weight of tetramethoxysilane and r-glycidoxypropylene were added. 50 parts by weight of trimethoxysilane was dissolved in 40 parts by weight of isopropyl alcohol, and 1 part of α05 normal salt solution was added.
After adding 0 parts by weight and stirring at room temperature for 8 hours,
! (L2 (f)) and 10 parts by weight of polyoxyalkylene ether were added and thoroughly stirred. The solution was coated on the lens obtained above by dipping, and 1
It was cured for 2 hours at 30°C. The results were good as in Example-1.
第１図は防曇性レンズの断面を示す図である。 以上 代理人 弁理士 最上 務 FIG. 1 is a diagram showing a cross section of an antifogging lens. that's all Agent Patent Attorney Mogami
Claims (1)
表面硬度の充分に高い樹脂被膜層を設けてなる吸湿性能
を有す表面硬度の高い防曇性プラスチックレンズ。An anti-fog plastic lens with a high surface hardness and moisture absorbing performance, which is made by providing a resin coating layer containing a surfactant and having a sufficiently high surface hardness on a lens base made of a hygroscopic resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57020355A JPS58137801A (en) | 1982-02-10 | 1982-02-10 | Anti-fogging plastic lens |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57020355A JPS58137801A (en) | 1982-02-10 | 1982-02-10 | Anti-fogging plastic lens |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS58137801A true JPS58137801A (en) | 1983-08-16 |
Family
ID=12024800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57020355A Pending JPS58137801A (en) | 1982-02-10 | 1982-02-10 | Anti-fogging plastic lens |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58137801A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4769259A (en) * | 1986-10-13 | 1988-09-06 | Nogawa Chemical Co., Ltd. | Method for preventing fogging of surfaces |
-
1982
- 1982-02-10 JP JP57020355A patent/JPS58137801A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4769259A (en) * | 1986-10-13 | 1988-09-06 | Nogawa Chemical Co., Ltd. | Method for preventing fogging of surfaces |
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