JPH09258003A - Contamination prevented lens - Google Patents

Contamination prevented lens

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Publication number
JPH09258003A
JPH09258003A JP6625096A JP6625096A JPH09258003A JP H09258003 A JPH09258003 A JP H09258003A JP 6625096 A JP6625096 A JP 6625096A JP 6625096 A JP6625096 A JP 6625096A JP H09258003 A JPH09258003 A JP H09258003A
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layer
group
compd
fluorine
lens
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JP6625096A
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Japanese (ja)
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Shinsuke Ochiai
Yukio Yasunori
幸雄 康乗
伸介 落合
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Sumitomo Chem Co Ltd
住友化学工業株式会社
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Abstract

PROBLEM TO BE SOLVED: To obtain high contamination preventing property, to easily remove contaminant and to maintain its effect by forming the layer of a specified fluorine-contg. silane compd. on the surface of a lens. SOLUTION: The layer of a fluorine-contg. silane compd. expressed by the formula and having 5×10<2> to 1×10<5> mol.wt. is formed on the surface of a lens. In formula, Rf is a straight or branched perfluoroalkyl group having 1 to 16 carbon number, X is iodine or hydrogen, Y is hydrogen or a lower alkyl group, Z is fluorine or a trifluoromethyl group, R<1> is a group which can be hydrolyzed, R<2> is hydrogen or an inactive univalent org. group, a, b, c, d are integers 0 to 200, e is 0 or 1, m and n are integers 0 to 2, and p is an integer 1 to 10. The layer of the fluorine-contg. silane compd. may be directly formed on the surface of a lens body, or an antireflection film comprising a hard coating layer and/or inorg. compd layer may be preliminarily formed on the surface of the base body.

Description

【発明の詳細な説明】 DETAILED DESCRIPTION OF THE INVENTION

【0001】 [0001]

【発明の属する技術分野】本発明はカメラ、眼鏡等に用いられるレンズに関する。 The present invention relates to a camera, a lens for use in spectacles or the like. 詳しくは防汚性を付与したレンズに関する。 For more information about the lens imparted with antifouling properties.

【0002】 [0002]

【従来の技術】眼鏡レンズやカメラ等のレンズには、光の反射を押さえ、光の透過性を高めるために、通常、その表面に反射防止処理が施されている。 BACKGROUND OF THE INVENTION eyeglass lenses and camera or the like of the lens, pressing the reflection of light, in order to increase the permeability of light, usually is applied antireflection treatment on the surface thereof. しかしながら、 However,
レンズ特に眼鏡レンズ等では、人が使用するに際し、手垢、指紋、汗、化粧料等の付着があり、反射防止膜を形成させると、その付着による汚れが目立ちやすく、またその汚れがとれにくくなる。 Lens in particular spectacle lenses or the like, when people use, finger marks, fingerprints, sweat, there is deposition of cosmetics and to form an anti-reflection film, comprising the fouling is conspicuous by also hardly take its dirty .

【0003】そこで、汚れにくく、あるいは汚れを拭き取りやすくするために、反射防止膜の表面に更に防汚層を設ける工夫がなされている。 [0003] Therefore, in order to facilitate wiping the dirt hardly, or dirt, further devised to provide an antifouling layer on the surface of the antireflection film it is made. 例えば、特開昭62−8 For example, JP-A-62-8
0603公報では、反射防止層上に末端にシラノール基を有する有機ポリシロキサンを皮膜した眼鏡レンズが提案されている。 In 0603 publication, spectacle lenses coating the organopolysiloxane having a silanol group at an end on the antireflection layer has been proposed. 更に特開昭61−247743公報では、プラスチック表面にポリフルオロアルキル基を含むモノ及びジシラン化合物およびハロゲン、アルキル、またはアルコキシのシラン化合物とからなる反射防止膜を有する低反射性と防汚性を有する低反射プラスチックが提案されている。 In addition JP 61-247743 Laid have low reflectivity and stain resistance with mono- and disilane compound containing a polyfluoroalkyl group to the plastic surface and halogen, alkyl, or an anti-reflection film made of alkoxy silane compound low-reflection plastic have been proposed.

【0004】 [0004]

【発明が解決しようとする課題】しかしながら、従来の提案された物品の耐汚染性は、それなりに効果のあるものの未だ充分ではない。 However [0007], the stain resistance of the conventional proposed article is not yet sufficient although effective in its own way. 特に、付着した汚染物は拭き取りにくく、また拭き取るときに水や有機溶剤を用いるために、耐汚染性を発現する物質が除かれやすく、耐汚染性の永続性に乏しい。 In particular, contaminants adhered hardly wipe, in order to use the water or an organic solvent when also wipe tends substance expressing a stain resistance is removed, poor stain resistance persistence.

【0005】本発明者はかかる事情に鑑み、防汚性に優れたレンズを得るべく鋭意検討した結果、レンズ表面に特定の含フッ素シラン化合物の層を形成することにより、汚染防止性がより高いのみならず、汚染物の除去が容易でしかもその効果が永続することを見出し、本発明に至った。 [0005] The present inventors have view of such circumstances, anti to obtain an excellent lens-fouling properties a result of extensive studies, by forming a layer of a specific fluorine-containing silane compound on the surface of the lens, a higher antifouling properties not only, it is easy to remove contaminants moreover found that the effect is persistent, leading to the present invention.

【0006】 [0006]

【課題を解決するための手段】すなわち本発明は、レンズ表面に一般式 化3で示され、分子量が5×10 2 Means for Solving the Problems] The present invention is illustrated in the lens surface by the formula of 3, a molecular weight of 5 × 10 2 ~
1×10 5の含フッ素シラン化合物の層を形成してなる防汚性レンズである。 Proof by forming a layer of 1 × 10 5 of the fluorine-containing silane compound is a stain resistant lens.

【化3】 [Formula 3] (式中、R fは炭素数1〜16の直鎖状または分岐状パーフルオロアルキル基、Xはヨウ素または水素、Yは水素または低級アルキル基、Zはフッ素またはトリフルオロメチル基、R 1は加水分解可能な基、R 2は水素または不活性な一価の有機基、a、b、c、dは0〜200 (Wherein, R f is a linear or branched perfluoroalkyl group, X is iodine or hydrogen, Y is hydrogen or a lower alkyl group, Z is fluorine or a trifluoromethyl group having 1 to 16 carbon atoms, R 1 is hydrolyzable group, R 2 is hydrogen or an inert monovalent organic group, a, b, c, d is 0 to 200
の整数、eは0または1、mおよびnは0〜2の整数、 Integer, e is 0 or 1, m and n is an integer of 0 to 2,
pは1〜10の整数を表す。 p is an integer of 1 to 10. ) 以下、本発明を詳細に説明する。 ) The present invention will be described in detail.

【0007】 [0007]

【発明の実施の形態】本発明のレンズ基材としては、ガラス、プラスチック等が挙げらる。 The lens substrate of the embodiment of the present invention, glass, plastic and the like Ageraru. プラスチックとしては透明であれば特に限定されるものではないが、例えば、アクリル系樹脂、ポリカーボネート系樹脂、ジエチレングリコールビスアリルカーボネート樹脂、ポリエチレンテレフタレート等のポリエステル系樹脂、トリアセチルセルロース、ジアセチルセルロース等のセルロース系樹脂、スチレン系樹脂、塩化ビニル系樹脂等が挙げられる。 Is not particularly limited so far as it is transparent plastic, for example, acrylic resin, polycarbonate resin, diethylene glycol bis allyl carbonate resin, polyester resin such as polyethylene terephthalate, triacetyl cellulose, cellulose such as diacetyl cellulose resins, styrene resins, vinyl resins such as chloride. これらの樹脂中には、耐候性改良のための紫外線吸収剤、その他の改質用に酸化防止剤、着色剤、難燃剤等の各種添加剤が含まれていても構わない。 During these resins, UV absorbers for weather resistance improvement, other antioxidants for reforming colorant, may be contained various additives such as flame retardants.

【0008】レンズ基材表面に、直接含フッ素シラン化合物層を設けても良いが、予め該基材表面にハードコート層および/または無機化合物の層からなる反射防止膜を付与しておいても良い。 [0008] surface of the lens substrate, it may be provided directly fluorine-containing silane compound layer, but be previously providing an antireflection film comprising a layer of pre-hard coat layer to the substrate surface and / or inorganic compounds good.

【0009】ハードコート層を設けることにより基材表面の硬度が増し傷が付きにくくなるのと同時に、表面が平滑になるため、反射防止膜を形成する際にその密着性が向上する。 [0009] Simultaneously as hardly scratched increases the hardness of the substrate surface by forming a hard coat layer, the surface becomes smooth, thereby improving the adhesion at the time of forming the antireflection film. 該ハードコート層としてはこの用途に用いられる公知のものでよい。 As the hard coat layer may be of known used for this purpose. 原料は例えば多官能性モノマーを主成分として重合硬化させることにより得られる硬化膜を挙げることができる。 Raw material can be cited cured film obtained by polymerizing curing as the main component, for example, polyfunctional monomers. 具体的にはウレタン(メタ)アクリレート、ポリエステル(メタ)アクリレート、ポリエーテル(メタ)アクリレート等のアクリロイル基、メタクリロイル基を2つ以上含んだ多官能重合性化合物を紫外線、電子線等の活性化エネルギー線によって重合硬化させた層;またはシリコン系、メラミン系、 Specifically, the urethane (meth) acrylate, polyester (meth) acrylates, polyether (meth) acryloyl group acrylate, ultraviolet polyfunctional polymerizable compound containing two or more methacryloyl groups, the activation energy of the electron beam or the like layer was polymerized cured by line; or silicone type, melamine type,
エポキシ系の架橋性樹脂原料を熱によって架橋硬化させたものなどを挙げることができる。 Epoxy crosslinkable resin raw material and the like that is crosslinked and cured by heat.

【0010】ハードコート層を形成させる方法としては、まず、原料を通常のコーティング作業で用いられる方法で、つまりスピン塗装、浸漬塗装、ロールコート塗装、グラビアコート塗装、カーテンフロー塗装等で塗布する。 [0010] As a method for forming the hard coat layer is first raw material in a method used in the usual coating operations, i.e. the spin coating, dip coating, roll coating painting, gravure coating paint is applied by curtain flow coating or the like. 続いて用いた原料に応じた方法により硬化させる。 It is cured by a method corresponding to subsequently employed material. この際被覆しやすくするために、あるいは被覆膜の膜厚を調整するために該原料を種々の溶剤により希釈しても構わない。 For this case easily coated, or in order to adjust the thickness of the coating film may be a raw material diluted with various solvents. ハードコート層の原料層を硬化させるには、加熱昇温する熱重合、紫外線や電子線などの活性エネルギー線の照射による光重合がある。 To cure the material layer of the hard coat layer is Atsushi Nobori thermal polymerization, there is a photopolymerization by irradiation with active energy rays such as ultraviolet rays or electron beams.

【0011】ハードコート層の厚さは特に限定されるものではないが、1〜20μmが好ましい。 [0011] The thickness of the hard coat layer is not particularly limited, 1 to 20 [mu] m is preferred. 1μmより薄くなると上層の反射防止層の影響で光の干渉模様が現れ、外観上好ましくない。 When thinner than 1μm interference pattern of light appears to the influence of the upper layer of the antireflection layer, the appearance is not preferable. また20μmより厚くなると塗膜にひびが入るなど、膜の強度上好ましくない。 Further, if the thickness is more than 20μm, such as crack in the coating film, the strength of the film is not preferred.

【0012】なお、透明基材とハードコート層との密着性を向上させるために、透明基材とハードコート層の間に接着層を設けても構わない。 [0012] In order to improve the adhesion between the transparent substrate and the hard coat layer, it may be provided an adhesive layer between the transparent substrate and the hard coat layer. その接着層としてはこの用途に用いられる公知のものでよい。 As the adhesive layer may be of known used for this purpose.

【0013】反射防止膜はレンズ基材の表面に直接、またはレンズ基材表面に形成したハードコート層の表面に付与する。 [0013] antireflection film is applied to the surface of the hard coat layer formed directly or lens substrate surface to the surface of the lens substrate. 反射防止膜は無機酸化物、または無機ハロゲン化物などの無機化合物の単層または多層の薄膜からなる公知のもので良く、真空蒸着法、イオンプレーティング法、スパッタリング法などの公知の方法により形成する。 Antireflection film can be of known consisting of a single layer or a multilayer of a thin film of an inorganic oxide, or inorganic compounds such as inorganic halides, a vacuum deposition method, ion plating method, formed by a known method such as a sputtering method .

【0014】なお、用いられる無機化合物としては、例えば、酸化イットリウム、二酸化珪素、酸化アルミニウム、酸化マグネシウム、酸化トリウム、酸化スズ、酸化ランタン、一酸化珪素、酸化インジウム、酸化ネオジウム、酸化アンチモン、酸化ジルコニウム、酸化セリウム、酸化チタン、酸化ビスマスなどの無機酸化物、フッ化カルシウム、フッ化ナトリウム、フッ化リチウム、フッ化マグネシウム、フッ化ランタン、フッ化ネオジウム、フッ化セリウム、フッ化鉛等の無機ハロゲン化物、 [0014] As the inorganic compound used, for example, yttrium oxide, silicon dioxide, aluminum oxide, magnesium oxide, thorium oxide, tin oxide, lanthanum oxide, silicon monoxide, indium oxide, neodymium oxide, antimony oxide, zirconium oxide , cerium oxide, titanium oxide, inorganic oxides such as bismuth oxide, calcium fluoride, sodium fluoride, lithium fluoride, magnesium fluoride, lanthanum fluoride, neodymium fluoride, cerium fluoride, inorganic halogen lead fluoride or the like monster,
硫化亜鉛、硫化カドミウム、三硫化アンチモン等の硫化物、セレン化亜鉛、テルル化カドミウム、テルル化鉛、 Zinc sulfide, cadmium sulfide, sulfides such as antimony trisulfide, zinc selenide, cadmium telluride, lead telluride,
珪素、ゲルマニウム、テルルなどを挙げることができる。 Mention may be made of silicon, germanium, tellurium and the like.

【0015】汚染防止性を付与する含フッ素シラン化合物は、前記一般式 化3で示さる。 The fluorine-containing silane compound to impart antifouling property, Shimesaru by formula of 3. 一般式 化3中のR R in the general formula of 3
fは炭素数1〜16の直鎖状または分岐状パーフルオロアルキル基であるが、好ましくはCF 3 −,C 2 f Although a linear or branched perfluoroalkyl group having 1 to 16 carbon atoms, preferably CF 3 -, C 2 F
5 −,C 37 −である。 5 -, C 3 F 7 - a. 1の加水分解可能な基として、ハロゲン、−OR 3 、−OCOR 3 、−OC(R 3 ) As hydrolyzable group of R 1, halogen, -OR 3, -OCOR 3, -OC (R 3)
=C(R 4 ) 2 、−ON=C(R 3 ) 2 、−ON=CR 5が好ましい(ただし、R 3は脂肪族炭化水素基または芳香族炭化水素基、R 4は水素または低級脂肪族炭化水素基、R 5は炭素数3〜6の二価の脂肪族炭化水素基である。)。 = C (R 4) 2, -ON = C (R 3) 2, -ON = CR 5 is preferred (although, R 3 is an aliphatic hydrocarbon group or an aromatic hydrocarbon group, R 4 is hydrogen or lower aliphatic family hydrocarbon group, R 5 is a divalent aliphatic hydrocarbon group having 3 to 6 carbon atoms.). さらに好ましくは、塩素、−OCH 3 、−OC More preferably, chlorine, -OCH 3, -OC
25である。 It is a 2 H 5. 2は水素または不活性な一価の有機基であるが、好ましくは、炭素数1〜4の一価の炭化水素基である。 R 2 is hydrogen or an inert monovalent organic group, but is preferably a monovalent hydrocarbon group having 1 to 4 carbon atoms. a、b、c、dは0〜200の整数であるが、好ましくは1〜50であり、eは0または1である。 a, b, c, d is an integer of 0 to 200, preferably 1 to 50, e is 0 or 1. mおよびnは0〜2の整数であるが、好ましくは0 m and n is an integer of 0 to 2, preferably 0
である。 It is. pは1以上の整数であり、好ましくは1〜10 p is an integer of 1 or more, preferably 1 to 10
の整数である。 Of an integer.

【0016】また分子量は5×10 2 〜1×10 5であるが、好ましくは5×10 2 〜1×10 4である。 [0016] Although the molecular weight of 5 × 10 2 ~1 × 10 5 , preferably from 5 × 10 2 ~1 × 10 4 .

【0017】また、上記一般式 化3で示される含フッ素シラン化合物の好ましい構造のものとして、下記一般式 化4で示されるものが挙げられる。 Further, as a preferable structure of the fluorine-containing silane compound represented by the general formula of 3 include those represented by the following general formula of 4.

【化4】 [Of 4] (式中、Yは水素または低級アルキル基、R 1は加水分解可能な基、pは1以上の整数を、qは1〜50の整数を、mは0〜2の整数を表す。) (Wherein, Y is hydrogen or a lower alkyl group, R 1 is a hydrolyzable group, p is an integer of 1 or more, q is an integer of 1 to 50, m represents an integer of 0 to 2.)

【0018】これらの含フッ素シラン化合物は市販のパーフルオロポリエーテルをシラン処理することによって得ることができる。 [0018] These fluorine-containing silane compound can be obtained by silane treatment of commercially available perfluoropolyether. 例えば、特開平1−294709号公報に開示のあるごとくである。 For example, it is as a disclosed in JP-A-1-294709.

【0019】含フッ素シラン化合物の層はレンズ基材の表面に直接、ハードコート層の表面または反射防止膜の表面に形成される。 The layer of fluorine-containing silane compound directly to the surface of the lens substrate, is formed on the surface of the surface or the anti-reflection film of the hard coat layer. 含フッ素シラン化合物層を形成させるには、ハードコート層の形成の際の原料塗布と同様な塗布方法によればよい。 To form a fluorine-containing silane compound layer, according to the material coating the same coating method in the formation of the hard coat layer. すなわち、スピン塗装、浸漬塗装、ロールコート塗装、グラビアコート塗装、カーテンフロー塗装等が用いられる。 Namely, spin coating, dip coating, roll coating painting, gravure coating paint, curtain flow coating or the like is used. なお、塗布する際には溶剤で希釈する方が塗布しやすい。 Incidentally, it is easily applied towards dilution with solvents when coating. その溶剤としては、パーフルオロヘキサン、パーフルオロメチルシクロヘキサン、パーフルオロ−1,3−ジメチルシクロヘキサン等が挙げられる。 As the solvent, perfluorohexane, perfluoro methyl cyclohexane, perfluoro-1,3-dimethylcyclohexane and the like.

【0020】また、含フッ素シラン化合物層は前述した方法以外に真空蒸着法により設けることもできる。 [0020] The fluorine-containing silane compound layer may also be provided by a vacuum deposition method other than the method described above. その際には原料化合物は高濃度、または希釈溶剤なしに使用することができる。 Starting compound in that case can be used without a high concentration or diluting solvent.

【0021】含フッ素シラン化合物層の厚さは特に限定されるものではないが、0.001〜0.5μm、好ましくは0.001〜0.03μmである。 [0021] The thickness of the fluorine-containing silane compound layer is not particularly limited, 0.001 to 0.5 [mu] m, preferably 0.001~0.03Myuemu. 0.001μ 0.001μ
mより薄いと防汚効果が乏しくなり、0.5μmより厚くなると表面がべたつくので好ましくない。 Thin and antifouling effect than m becomes poor, undesirably sticky is thickened the surface than 0.5 [mu] m. また防汚層を反射防止膜表面に設けた場合には、防汚層の厚さが0.03μmより厚くなると反射防止効果が低下するため好ましくない。 Further proof when provided in the proofing layer antireflection film surface is not preferable because the thickness of the antifouling layer is lowered thicker the antireflection effect than 0.03 .mu.m.

【0022】 [0022]

【発明の効果】本発明のレンズは、汚染防止性が高く、 Lens of the present invention according to the present invention has a high pollution resistance,
その効果が永続し、しかも汚染物の除去が容易である。 Its effect is permanent, yet is easy to remove contaminants.

【0023】 [0023]

【実施例】以下、本発明を実施例により更に詳細に説明するが、本発明は実施例に限定されるものではない。 EXAMPLES Hereinafter, further detailed explanation of the present invention embodiment, the present invention is not limited to the examples. なお、実施例において各種の物性の評価試験方法は以下の通りである。 The evaluation test methods of various physical properties in Examples are as follows. (1)水に対する接触角;接触角計(CA−A型:協和界面科学(株))を使用し、室温下で直径1.0mmの水滴を針先につくり、これを基材の表面に触れさせて液滴を作った。 (1) Contact angle with water; contact angle meter: using (CA-A type manufactured by Kyowa Interface Science Co.), to make a water droplet diameter 1.0mm to needle tip at room temperature, which on the surface of the substrate let me touch made the liquid droplet. このときに生ずる液滴と面との角度を測定し接触角とした。 The angle between the droplet and the surface generated at this time was measured contact angle. (2)耐久性;セルロース製不織布(ベンコット:旭化成)により、基材の表面を20往復拭き取った後に、前述した方法で水に対する接触角を測定することで耐久性試験を行った。 (2) Durability; cellulose nonwoven fabric: by (Bemcot Asahi Kasei), the surface of the base material after wiping back and forth 20 times, the durability test was performed by measuring the contact angle with water in the manner described above. (3)指紋の付着性;基材表面に右手親指を三秒間押しつけて、指紋を付着させて、そのつき易さあるいは目立ち易さを目視判定した。 (3) adhesion of the fingerprint; against three seconds right thumb on the substrate surface, by adhering the fingerprint was visually judged ease or conspicuous ease per the. 判定基準は次の通りとした。 Criteria were as follows. ○:指紋の付着が少なく、付いた指紋が目立たない。 ○: adhesion of the fingerprint is small, with fingerprint is not noticeable. ×:指紋の付着が明確に認識できる。 ×: adhesion of the fingerprint can be clearly recognized. (4)指紋の拭き取り性;付着した指紋をセルロース製不織布で拭き取り、指紋のとれ易さを目視判定した。 (4) wiping of the fingerprint; wiping adhered fingerprint cellulose nonwoven fabric was visually judged take easily the fingerprint. 判定基準は以下の通りとした。 Criteria were as follows. ○:指紋を完全に拭き取ることができる。 ○: can be wiped off the fingerprint to complete. △:指紋の拭き取り跡が残る。 △: wiping fingerprints remain. ×:指紋の拭き取り跡が広がり、除去することが困難である。 ×: spread wiping traces of fingerprints, it is difficult to remove.

【0024】実施例1 下式 化5で示される含フッ素シラン化合物(分子量: The fluorine-containing silane compound represented by Example 1 below Formulation 5 (molecular weight:
約5000、ダイキン工業(株)製)をパーフルオロヘキサンで希釈して濃度が2.0g/Lの溶液とした。 About 5000, the concentration by diluting Daikin Industries Co., Ltd., Ltd.) in perfluorohexane was a solution of 2.0 g / L.

【0025】 [0025]

【化5】 [Of 5] ガラス製のレンズをこの溶液に浸漬し、15cm/分の速度で引き上げて塗布した。 The glass lens was immersed in this solution, was applied and pulled up at 15cm / min. 塗布後は室温条件下で一昼夜放置して溶剤を揮散させ、含フッ素シラン化合物の層が付与されたガラスレンズを得た。 After coating the solvent is vaporized to stand overnight at room temperature conditions, to obtain a glass lens a layer of fluorine-containing silane compound is applied. 各種物性を評価した結果を表1に示した。 The results of evaluation of various physical properties are shown in Table 1.

【0026】実施例2 ガラスレンズの表面に特開昭56−113101号公報の実施例に準じて、真空蒸着装置((株)シンクロン製;BMC−700)を用い、二酸化珪素、酸化チタン、二酸化珪素、酸化チタン、二酸化珪素の順序で5層の薄膜を形成し、反射防止膜を形成させた。 [0026] according to an embodiment of JP 56-113101 JP on the surface of Example 2 glass lenses, a vacuum vapor deposition apparatus (Co. SYNCHRON manufactured; BMC-700) using a silicon dioxide, titanium oxide, dioxide silicon, titanium oxide, to form a thin film of five layers in the order of silicon dioxide, to form an antireflection film. このガラスレンズを用いて実施例1と同様にして、含フッ素シラン化合物の層を形成したガラスレンズを得た。 In the same manner as in Example 1 by using this glass lens, to obtain a glass lens to form a layer of fluorine-containing silane compound. 各種物性を評価した結果を表1に示した。 The results of evaluation of various physical properties are shown in Table 1.

【0027】実施例3 ポリカーボネート樹脂製のレンズにプライマー液CP1 The primer solution CP1 in Example 3 Polycarbonate resin lens
108(日本エーアールシー(株)製)を浸漬塗布し1 108 (Japan er Earl Sea made Co., Ltd.) and the dip coating 1
時間室温で乾燥させた後、ハードコート液クリスタルコートC−220(日本エーアールシー(株)製)を浸漬塗布した。 After drying at the time room temperature, a hard coat solution Crystal Court C-220 (manufactured by Nippon er Earl Sea Corporation) was coated by dipping. 室温で1時間乾燥させた後110℃で1時間加熱硬化させた。 Cured by heating 1 hour at 110 ° C. After drying for 1 hour at room temperature. 得られた表面硬化ポリカーボネート樹脂製レンズを用いて実施例1と同様にして、含フッ素シラン化合物の層を形成したガラスレンズを得た。 Using the obtained surface hardened polycarbonate resin lens of Example 1 in the same manner as to obtain a glass lens to form a layer of fluorine-containing silane compound. 各種物性を評価した結果を表1に示した。 The results of evaluation of various physical properties are shown in Table 1.

【0028】実施例4 実施例3と同様にして作成した表面硬化ポリカーボネート樹脂製レンズの表面に実施例2と同様の方法で反射防止膜を形成させた。 [0028] to form an antireflection film in the same manner as in Example 2 on the surface of the surface hardening polycarbonate resin lens was produced in the same manner as in Example 4 Example 3. さらにこのレンズを用いて実施例1 Furthermore with reference to the lens of Example 1
と同様にして、含フッ素シラン化合物の層を形成したガラスレンズを得た。 In the same manner as to obtain a glass lens to form a layer of fluorine-containing silane compound. 各種物性を評価した結果を表1に示した。 The results of evaluation of various physical properties are shown in Table 1.

【0029】実施例5 ポリメチルメタクリレート樹脂製レンズの表面に、固形分が30%となるようにトルエンで希釈したウレタンアクリレート系ハードコート剤(ユニディック17−80 [0029] surface of the Example 5 polymethyl methacrylate resin lens, a solid content of 30 percent so as urethane acrylate-based hard coating agent was diluted with toluene (UNIDIC 17-80
6:大日本インキ化学工業(株))を浸漬塗布し、室温で30分間乾燥した後に、120Wのメタルハライドランプ(アイグラフィックス社製UB0451)を20c 6: Dainippon Ink & Chemicals, was dip-coated with Co.), after drying for 30 minutes at room temperature, 120 W metal halide lamp (Eye Graphics Co. UB0451) 20c
mの距離から10秒間照射することにより硬化膜を形成させた。 To form a cured film by irradiating for 10 seconds from a distance of m. この硬化膜上に実施例2と同様の方法で反射防止膜を形成させた。 To form a reflection preventing film in the same manner as in Example 2 on the cured film. さらにこのレンズを用いて実施例1 Furthermore with reference to the lens of Example 1
と同様にして、含フッ素シラン化合物の層を形成したガラスレンズを得た。 In the same manner as to obtain a glass lens to form a layer of fluorine-containing silane compound. 各種物性を評価した結果を表1に示した。 The results of evaluation of various physical properties are shown in Table 1.

【0030】比較例1 実施例1において、含フッ素シラン化合物の層を形成せずに、ガラスレンズをそのまま評価した。 [0030] In Comparative Example 1 Example 1, without forming a layer of a fluorine-containing silane compound, it was directly evaluated glass lens. 各種物性を評価した結果を表1に示した。 The results of evaluation of various physical properties are shown in Table 1.

【0031】比較例2 実施例3の表面硬化ポリカーボネート樹脂製レンズを、 [0031] The surface hardening polycarbonate resin lens of Comparative Example 2 Example 3,
含フッ素シラン化合物の層を形成せずに評価した。 It was evaluated without forming a layer of a fluorine-containing silane compound. 各種物性を評価した結果を表1に示した。 The results of evaluation of various physical properties are shown in Table 1.

【0032】比較例3 実施例5の反射防止ポリメチルメタクリレート樹脂製レンズを、含フッ素シラン化合物の層を形成せずに評価した。 [0032] The antireflection polymethyl methacrylate resin lens of Comparative Example 3 Example 5 was evaluated without forming a layer of a fluorine-containing silane compound. 各種物性を評価した結果を表1に示した。 The results of evaluation of various physical properties are shown in Table 1.

【0033】比較例4 C 8 F 17 C 2 H 4 Si(OCH 3 ) 3をイソプロピルアルコールで希釈し2.0g/Lの溶液を調整し、その溶液100部に対し0.1規定の塩酸水溶液を3部添加したものを処理液とした。 [0033] Comparative Example 4 C 8 F 17 C 2 H 4 Si (OCH 3) 3 was diluted with isopropyl alcohol to prepare a solution of 2.0 g / L, hydrochloric acid aqueous solution of 0.1 N to the solution 100 parts It was treated solution obtained by adding 3 parts. 含フッ素シラン化合物の層を形成する前の実施例1と同じガラスレンズにこの処理液を浸漬塗布し、室温で1時間乾燥後110℃で1時間加熱硬化させ、含フッ素シラン化合物の層を形成させたガラスレンズを得た。 The treatment liquid was dip-coated in the same glass lens of Example 1 before the formation of the layer of the fluorine-containing silane compound with heating for 1 hour curing at 110 ° C. After 1 hour drying at room temperature, forming a layer of fluorine-containing silane compound to obtain a glass lens is.
各種物性を評価した結果を表1に示した。 The results of evaluation of various physical properties are shown in Table 1.

【0034】比較例5 含フッ素シラン化合物の層を形成する前の実施例3と同じ表面硬化ポリカーボネート樹脂製レンズを、比較例4 [0034] The same surface hardened polycarbonate resin lens of Example 3 before the formation of the layer of Comparative Example 5 fluorine-containing silane compound, Comparative Example 4
と同様の方法で含フッ素シラン化合物の層を形成させたレンズを得た。 To obtain a lens obtained by forming a layer of fluorine-containing silane compound in a similar manner to that. 各種物性を評価した結果を表1に示した。 The results of evaluation of various physical properties are shown in Table 1.

【0035】比較例6 含フッ素シラン化合物の層を形成する前の実施例5と同じ反射防止ポリメチルメタクリレート樹脂製レンズを、 [0035] The same antireflection polymethyl methacrylate resin lens of Example 5 before the formation of the layer of Comparative Example 6 fluorine-containing silane compound,
比較例4と同様の方法で含フッ素シラン化合物の層を形成させたレンズを得た。 To obtain a lens obtained by forming a layer of fluorine-containing silane compound in the same manner as in Comparative Example 4. 各種物性を評価した結果を表1 Table 1 the results of evaluation of the various physical properties
に示した。 It was shown to.

【0036】 [0036]

【表1】 [Table 1]

Claims (3)

    【特許請求の範囲】 [The claims]
  1. 【請求項1】 レンズ表面に、一般式 化1で示され、 To 1. A lens surface, represented by the general formula of 1,
    分子量が5×10 2 〜1×10 5の含フッ素シラン化合物の層を形成してなる防汚性レンズ。 Antifouling lens molecular weight is to form a layer of 5 × 10 2 ~1 × 10 5 of the fluorine-containing silane compound. 【化1】 [Formula 1] (式中、R fは炭素数1〜16の直鎖状または分岐状パーフルオロアルキル基、Xはヨウ素または水素、Yは水素または低級アルキル基、Zはフッ素またはトリフルオロメチル基、R 1は加水分解可能な基、R 2は水素または不活性な一価の有機基、a、b、c、dは0〜200 (Wherein, R f is a linear or branched perfluoroalkyl group, X is iodine or hydrogen, Y is hydrogen or a lower alkyl group, Z is fluorine or a trifluoromethyl group having 1 to 16 carbon atoms, R 1 is hydrolyzable group, R 2 is hydrogen or an inert monovalent organic group, a, b, c, d is 0 to 200
    の整数、eは0または1、mおよびnは0〜2の整数、 Integer, e is 0 or 1, m and n is an integer of 0 to 2,
    pは1〜10の整数を表す。 p is an integer of 1 to 10. )
  2. 【請求項2】 含フッ素シラン化合物が一般式 化2で示される請求項1記載の防汚性レンズ。 Wherein antifouling lens according to claim 1, wherein the fluorine-containing silane compound represented by the general formula of 2. 【化2】 ## STR2 ## (式中、Yは水素または低級アルキル基、R 1は加水分解可能な基、rは1〜10の整数を、qは1〜50の整数を、mは0〜2の整数を表す。) (Wherein, Y is hydrogen or a lower alkyl group, R 1 is a hydrolyzable group, r is 1 to 10 integer, q is an integer of 1 to 50, m represents an integer of 0 to 2.)
  3. 【請求項3】 レンズ表面と含フッ素シラン化合物層との間にハードコート層および/または無機化合物の層からなる反射防止膜が介在する請求項1記載の防汚性レンズ。 3. A lens surface and the hard coat layer and / or antifouling lens according to claim 1, wherein the anti-reflection film comprising a layer of an inorganic compound is interposed between the fluorine-containing silane compound layer.
JP6625096A 1996-03-22 1996-03-22 Contamination prevented lens Withdrawn JPH09258003A (en)

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WO2009041580A1 (en) * 2007-09-28 2009-04-02 Nikon-Essilor Co., Ltd. Optical component and manufacturing method of the optical component
US8189261B2 (en) 2007-09-28 2012-05-29 Nikon-Essilor Co., Ltd. Optical component and method for manufacturing the same
JP5248516B2 (en) * 2007-09-28 2013-07-31 株式会社ニコン・エシロール The method of manufacturing an optical component, and optical component
JP2009145521A (en) * 2007-12-13 2009-07-02 Epson Toyocom Corp Optical element
KR101220824B1 (en) * 2010-06-29 2013-01-18 (주) 태양기전 Panel Coating Method
WO2012053418A1 (en) 2010-10-19 2012-04-26 日東電工株式会社 Highly flame-retardant polymer member, flame-retardant article, and flame-retarding method
JP2014505114A (en) * 2010-11-10 2014-02-27 ダウ・コーニング・コーポレイション Surface treatment composition, a manufacturing method of the surface treatment composition, and surface treated article
WO2012121374A1 (en) 2011-03-09 2012-09-13 日東電工株式会社 Shatterproofing member with hardenable pressure-sensitive adhesive layer
JP2016203478A (en) * 2015-04-22 2016-12-08 信越化学工業株式会社 Surface treatment agent containing fluorooxyalkyl group-containing polymer, and article treated with the surface treatment agent

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