JPH034671B2 - - Google Patents

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Publication number
JPH034671B2
JPH034671B2 JP57018639A JP1863982A JPH034671B2 JP H034671 B2 JPH034671 B2 JP H034671B2 JP 57018639 A JP57018639 A JP 57018639A JP 1863982 A JP1863982 A JP 1863982A JP H034671 B2 JPH034671 B2 JP H034671B2
Authority
JP
Japan
Prior art keywords
lenses
dyed
dyeing
synthetic resin
parts
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.)
Expired - Lifetime
Application number
JP57018639A
Other languages
Japanese (ja)
Other versions
JPS58136882A (en
Inventor
Kenji Kojima
Takao Mogami
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Seiko Epson Corp
Original Assignee
Seiko Epson Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Seiko Epson Corp filed Critical Seiko Epson Corp
Priority to JP57018639A priority Critical patent/JPS58136882A/en
Publication of JPS58136882A publication Critical patent/JPS58136882A/en
Publication of JPH034671B2 publication Critical patent/JPH034671B2/ja
Granted legal-status Critical Current

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Description

【発明の詳細な説明】 本発明は、高屈折率の難然性樹脂からなる合成
樹脂レンズを染色するための染色液に関する。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a dyeing liquid for dyeing synthetic resin lenses made of a highly refractory resin with a high refractive index.

1972年の米国のFDA規格の制定以来、眼鏡レ
ンズの安全性が世界的に見直されるようになつて
いる中で、レンズ材料としてより安全性の高い、
合成樹脂が、無機ガラスに代つて使用されるよう
になつてきた。無機ガラスから合成樹脂レンズへ
の移行は世界的な傾向であり、我国に於てもジエ
チレングリコールビスアリルカーボネート(商品
名CR−39、以下CR−39と略す)樹脂によるレン
ズはシエアを徐々に拡大し既に20%を越えたと言
われている。合成樹脂レンズは安全性(耐衝撃
性)が高いことに加え、軽い、加工性が良い、染
色が容易である等の多くの利点を有している。一
方合成樹脂レンズ材料の主流を占めるCR−39は
屈折率が150と低いため、レンズが厚くなるとい
う欠点があり、体裁感の良い、薄いプラスチツク
レンズに対する消費者の潜在的要求は非常に強
い。又比較的屈折率の高いポリカーボネート、ポ
リスチレン等は、熱可塑性樹脂であるため、玉摺
加工性、耐熱性、耐溶剤性に問題を残している。
Since the establishment of FDA standards in the United States in 1972, the safety of eyeglass lenses has been reviewed worldwide.
Synthetic resins have come to be used in place of inorganic glass. The shift from inorganic glass to synthetic resin lenses is a global trend, and even in Japan, lenses made of diethylene glycol bisallyl carbonate (product name CR-39, hereinafter abbreviated as CR-39) resin are gradually expanding their shear. It is said that it has already exceeded 20%. In addition to high safety (impact resistance), synthetic resin lenses have many advantages such as being lightweight, easy to process, and easy to dye. On the other hand, CR-39, which is the mainstream synthetic resin lens material, has a low refractive index of 150, which has the disadvantage of making the lens thicker, so there is a strong latent consumer demand for thin plastic lenses that are comfortable to wear. Furthermore, since polycarbonate, polystyrene, etc. having a relatively high refractive index are thermoplastic resins, there remain problems in beading processability, heat resistance, and solvent resistance.

このような状況を鑑み、特開昭55−13747号公
報あるいは特開昭56−166214号公報において、熱
硬化性で高屈折率の難然性樹脂からなる合成樹脂
レンズが提案された。これらの合成樹脂レンズ
は、一般式が〔〕式で表わされる一種以上の単
量体と一般式が〔〕式で表わされる一種以上の
単量体とを主成分とする共重合体からなり、屈折
率が1.60以上で、光学的な諸特性にもすぐれた合
成樹脂レンズが実現できるものである。
In view of this situation, a synthetic resin lens made of a thermosetting, high refractive index hard resin was proposed in JP-A-55-13747 and JP-A-56-166214. These synthetic resin lenses are made of a copolymer whose main components are one or more monomers whose general formula is represented by the formula [] and one or more monomers whose general formula is represented by the formula [], A synthetic resin lens with a refractive index of 1.60 or higher and excellent optical properties can be realized.

(但し、式中XおよびYはフツ素を除くハロゲン
または水素、Rは水素またはメチル基、mは1〜
5の整数、nは0〜3の整数を示す。) しかし、このような高屈折率の合成樹脂レンズ
には、以下のような欠点がある。
(However, in the formula, X and Y are halogen or hydrogen excluding fluorine, R is hydrogen or a methyl group, m is 1 to
An integer of 5, n represents an integer of 0 to 3. ) However, such high refractive index synthetic resin lenses have the following drawbacks.

すなわち、先に述べた合成樹脂レンズの利点の
うち、染色が容易であるという利点は、合成樹脂
レンズのシエア拡大に大きく貢献しており、現在
CR−39レンズは、その70%以上が染色されて販
売されていると言われている。したがつて、染色
が不可能な合成樹脂レンズは、商品価値が著しく
劣り、今後市場性を持ち得ないと言つても過言で
はないが、前述の高屈折率合成樹脂レンズは、従
来CR−39レンズの染色に用いられていた染色液
では、全く染色できないか、染色されても斑点状
にしか染色できず、均一に染色することができな
いという欠点を有している。
In other words, among the advantages of synthetic resin lenses mentioned above, the ease of dyeing has greatly contributed to the expansion of the market share of synthetic resin lenses, and currently
It is said that over 70% of CR-39 lenses are sold dyed. Therefore, it is no exaggeration to say that synthetic resin lenses that cannot be dyed have significantly inferior commercial value and will not have marketability in the future. The dyeing solutions used to dye lenses have the disadvantage that they cannot be dyed at all, or if they are dyed, they can only be dyed in spots, and cannot be dyed uniformly.

本発明者は、以上の点に鑑み、従来の染色液
に、染色補助剤すなわちキヤリヤーを添加するこ
とにより、前述の高屈折率合成樹脂レンズを容易
かつ均一に染色することが可能になることを見出
し、本発明の至つたものである。
In view of the above points, the present inventor has discovered that by adding a dyeing aid, ie, a carrier, to a conventional dyeing solution, it becomes possible to easily and uniformly dye the above-mentioned high refractive index synthetic resin lenses. Heading: Summary of the Invention.

すなわち、本発明の染色液は、水1に対して
キヤリヤーとして安息香酸エチルまたはサリチル
酸メチルのどちらかもしくは両者の混合物が0.5
〜50.0g、アニオン界面活性剤が0.2〜20.0g、分
散染料が0.5〜20.0gからなることを特徴とする。
That is, the dyeing solution of the present invention contains 0.5 parts of either ethyl benzoate or methyl salicylate or a mixture of both as a carrier to 1 part of water.
~50.0g, anionic surfactant from 0.2 to 20.0g, and disperse dye from 0.5 to 20.0g.

本発明の染色液は、前記〔〕式で表わされる
単量体の一種以上が9〜80重量部、前記〔〕式
で表わされる単量体の一種以上が20〜80重量部、
紫外線吸収剤、光安定剤等を含んだ混合液を、適
当なラジカル重合開始剤の存在下で共重合させる
ことによつて得られる合成樹脂レンズを均一に染
色するのに適当であり、該染色液に該合成樹脂レ
ンズを浸漬することにより染色することができ
る。
The dyeing solution of the present invention contains 9 to 80 parts by weight of one or more monomers represented by the above formula [], 20 to 80 parts by weight of one or more monomers represented by the above formula [],
It is suitable for uniformly dyeing synthetic resin lenses obtained by copolymerizing a liquid mixture containing an ultraviolet absorber, a light stabilizer, etc. in the presence of an appropriate radical polymerization initiator; The synthetic resin lens can be dyed by immersing it in a liquid.

染色液の液組成に関し、安息香酸のエチル、或
はサリチル酸メチル、又は両者の混合液の量が、
水1に対し0.5g以下の場合には、レンズがほ
とんど染色されず、50gを越えた場合には、キヤ
リヤーが均一に分散しきれず、レンズがまだらに
染色され易くなり、均一な染色が困難となる。ア
ニオン界面活性剤が水1に対し0.2g以下にな
ると、界面活性剤の種類にもよるが、キヤリヤー
及び分散染料を均一に分散させることができなく
なり、染料体の色むらを起こし易く、20.0gを越
すと、染色液が泡だち、染色がしにくくなるばか
りでなく、分散に対しての効果も向上しなくな
る。分散染料が0.5g以下の場合には分散染料の
種類にもよるが、染色に時間がかかり、20gを越
すと分散しにくくなり、液の底部に沈降し濃度が
増したための効果がなくなる。
Regarding the liquid composition of the staining solution, the amount of ethyl benzoate, methyl salicylate, or a mixture of both is
If the amount is less than 0.5g per 1 part of water, the lens will hardly be dyed, and if it exceeds 50g, the carrier will not be dispersed evenly and the lens will be easily dyed in spots, making uniform dyeing difficult. Become. If the amount of anionic surfactant is less than 0.2g per 1 part of water, depending on the type of surfactant, it becomes impossible to uniformly disperse the carrier and disperse dye, which tends to cause color unevenness of the dye body. If this is exceeded, not only will the dyeing solution become foamy, making it difficult to dye, but the dispersion effect will not improve. If the amount of disperse dye is less than 0.5 g, it will take time to dye, although it depends on the type of disperse dye, and if it exceeds 20 g, it will become difficult to disperse and will settle to the bottom of the liquid, increasing the concentration and eliminating the effect.

分散染料は、染色したい色調に応じて、市販の
もののうちから選択すれば良く、また適当な分散
染料を混合して用いられることもできる。又ぼか
し(グラデイエーシヨン)染色も、CR−39レン
ズと同様の方法により可能である。
Disperse dyes may be selected from commercially available ones depending on the desired color tone, and suitable disperse dyes may also be used in combination. Gradation dyeing is also possible using the same method as CR-39 lenses.

この染色された合成樹脂レンズは、真空蒸着に
よるSiO2、ZrO2、Al2O3のコーテイング、シリコ
ン系或はアクリル系の有機のハードコーテインも
十分可能である。
This dyed synthetic resin lens can be coated with SiO 2 , ZrO 2 , Al 2 O 3 by vacuum deposition, or coated with a silicon-based or acrylic-based organic hard coat.

以下、実施例により本発明を詳細に説明する。 Hereinafter, the present invention will be explained in detail with reference to Examples.

実施例 1 0−クロルスチレン50重量部、2,2−ビス
〔3,5−ジブロモー4−(2−メタクリロイルオ
キシエトキシ)フエニル〕プロパン50重量部、2
−(2′−ヒドロキシー5′−メチルフエニル)ベン
ゾトリアゾール0.5重量部、ジミリスチルパーオ
キシジカーボネート1.0重量部を混合した液をキ
ヤステイング法によりラジカル共重合させたレン
ズを染色液に浸漬し染色した。尚染色液の調整法
及び染方法方は次の通りである。
Example 1 50 parts by weight of 0-chlorostyrene, 50 parts by weight of 2,2-bis[3,5-dibromo4-(2-methacryloyloxyethoxy)phenyl]propane, 2
-(2'-Hydroxy-5'-methylphenyl)benzotriazole (0.5 parts by weight) and dimyristyl peroxydicarbonate (1.0 parts by weight) were radically copolymerized by the casting method, and then the lenses were immersed in the dyeing solution and dyed. The method for preparing the staining solution and the dyeing method are as follows.

50℃の水1に、界面活性剤としてニツサンシ
ントレツキス5g(日本油脂株式会社製)、キヤ
リヤーとして安息香酸エチル5gを混合し、1時
間撹拌した。
5 g of Nitsusan Syntrekis (manufactured by Nippon Oil & Fats Co., Ltd.) as a surfactant and 5 g of ethyl benzoate as a carrier were mixed in 1 part of water at 50°C, and the mixture was stirred for 1 hour.

次にカヤロンポリエステルライトレツドBL−
SE(日本化薬株式会社製)を2g加え30分間撹拌
した。更に液を90℃まで上昇させ30分間撹拌し、
染色液とした。この液に上記のレンズを2分間浸
漬し染色した。
Next is Kayalon Polyester Light Red BL-
2 g of SE (manufactured by Nippon Kayaku Co., Ltd.) was added and stirred for 30 minutes. Furthermore, the liquid was raised to 90℃ and stirred for 30 minutes.
It was used as a staining solution. The above lenses were immersed in this solution for 2 minutes and dyed.

結果は染色は均一にされ、可視部の平均透過率
は80%であつた。
As a result, the staining was uniform and the average transmittance in the visible area was 80%.

比較として、安息香酸エチル及びアニオン界面
活性剤を全く含まない染色液を同様の方法で調整
し染色した。安息香酸エチルを含まない染色液に
浸漬したレンズは30分間浸漬しても全く染色され
ず、界面活性剤を含まない液に浸漬したレンズは
斑点状に染色された。
For comparison, a staining solution containing no ethyl benzoate or anionic surfactant was prepared and dyed in the same manner. Lenses immersed in a staining solution that did not contain ethyl benzoate were not stained at all after 30 minutes of immersion, and lenses immersed in a solution that did not contain a surfactant were stained in spots.

実施例 2 スチレン60重量部、2,2−ビス〔4−(2−
メタクリロイルオキシエトキシ)フエニル〕プロ
パン40重量部、2−ヒドロキシー4−オクトキシ
ベンゾフエノン0.5重量部、ラウロイルパーオキ
シド1.5重量部を混合した液をキヤステイング法
によりラジカル共重合させたレンズを次に示す染
色液に浸漬し、染色した。
Example 2 60 parts by weight of styrene, 2,2-bis[4-(2-
The following is a lens obtained by radical copolymerization using a casting method of a liquid mixture of 40 parts by weight of methacryloyloxyethoxy)phenyl propane, 0.5 parts by weight of 2-hydroxy-4-octoxybenzophenone, and 1.5 parts by weight of lauroyl peroxide. It was dipped in a dyeing solution and dyed.

60℃の水1に、界面活性剤として日光ケミカ
ルズ株式会社製NES−203を7g、キヤリヤーと
して、サリチル酸メチル10gを混合し1時間撹拌
した。
7 g of NES-203 manufactured by Nikko Chemicals Co., Ltd. as a surfactant and 10 g of methyl salicylate as a carrier were mixed in 60°C water 1 and stirred for 1 hour.

この液にミケトンポリエステルブルーEB(三井
東圧化学株式会社)を3g加え30分間撹拌した。
次にこの液を90℃まで昇温させ、30分間撹拌し染
色液とした。この液に上記レンズを15分間浸漬
し、染色した。レンズは均一に染色され可視部の
平均透過率は50%であつた。
3 g of Miketon Polyester Blue EB (Mitsui Toatsu Chemical Co., Ltd.) was added to this solution and stirred for 30 minutes.
Next, this liquid was heated to 90°C and stirred for 30 minutes to obtain a staining liquid. The above lens was immersed in this solution for 15 minutes and dyed. The lens was uniformly dyed and the average transmittance in the visible area was 50%.

比較してサリチル酸メチル、及び界面活性剤を
含まない染色液を同様の方法により調整し、染色
した。サリチル酸メチルを全く含まない染色液に
浸漬したレンズは30分間浸漬しても全く染色され
ず、界面活性剤を含まない液に浸漬したレンズは
まだらに染色された。
In comparison, a staining solution containing no methyl salicylate or surfactant was prepared and dyed in the same manner. Lenses immersed in a dye solution containing no methyl salicylate were not dyed at all after 30 minutes of immersion, and lenses immersed in a solution containing no surfactant were stained in spots.

実施例 3 スチレン60重量部、2,2−ビス〔3,5−ジ
ブロモー4−(2−メタクリロイルオキシエトキ
シ)フエニル〕プロパン40重量部、2−(2′−ヒ
ドロキシ−5′メチルフエニル)ベンゾトリアゾー
ル0.3重量部、ジイソプロピルパーオキシジカー
ボネート1.0重量部を混合した液をキヤステイン
グ法によりラジカル共重合させたレンズを染色液
に浸漬し、染色した。尚染色液の調整法及び染色
方法は次の通りである。
Example 3 60 parts by weight of styrene, 40 parts by weight of 2,2-bis[3,5-dibromo4-(2-methacryloyloxyethoxy)phenyl]propane, 0.3 parts by weight of 2-(2'-hydroxy-5'methylphenyl)benzotriazole parts by weight and 1.0 parts by weight of diisopropyl peroxydicarbonate were radically copolymerized by the casting method, and the lenses were immersed in the dyeing solution and dyed. The method for preparing the staining solution and the staining method are as follows.

50℃の水1に界面活性剤としてニツサンラピ
ゾールB−30(日本油脂株式会社製)10g、安息
香酸エチル5g、キヤリヤーとしてサリチル酸メ
チル5gを加え1時間撹拌した。次にこの液にテ
ラシルブラツクB(チバガイギー株式会社製)を
5g加え30分間撹拌した。この混合液を85℃まで
昇温させ更に30分間撹拌し、染色液とした。ビス
タハーフマチツクを用い、10分間上記レンズをぼ
かし染色した。境界もなく、ぼかし染色がきれい
にできた。
10 g of Nitsusan Rapizole B-30 (manufactured by NOF Corporation) as a surfactant, 5 g of ethyl benzoate, and 5 g of methyl salicylate as a carrier were added to water 1 at 50° C. and stirred for 1 hour. Next, 5 g of Terrasil Black B (manufactured by Ciba Geigy Corporation) was added to this liquid and stirred for 30 minutes. This mixed solution was heated to 85° C. and further stirred for 30 minutes to obtain a dyeing solution. The lenses were blurred and stained for 10 minutes using Vista Half-Matic. There were no boundaries, and the blurred dyeing was done beautifully.

比較としてキヤリヤー及び皆面活性剤を含まな
い染色液を同様の方法で調整し染色した。キヤリ
ヤーを含まないレンズは全く染色されず、界面活
性剤を含まない染色液では、実施例1、2と同様
斑点状に染つたばかりでなく、境界線がはつきり
とでき、商点としての価値を持たなかつた。
For comparison, a dyeing solution containing no carrier and no surfactant was prepared and dyed in the same manner. Lenses containing no carrier were not dyed at all, and lenses containing no surfactant were dyed not only in spots like in Examples 1 and 2, but also with sharp border lines, making it difficult to use as a commercial point. It had no value.

Claims (1)

【特許請求の範囲】 1 水1に対してキヤリヤーとして安息香酸エ
チルまたはサルチル酸ネチルのどちらかもしくは
両者の混合物が0.5〜50.0g、アニオン界面活性
剤が0.2〜20.0g、分散染料が0.5〜20.0gからな
る染色液を用いて、一般式が[]で表される1
種以上の単量体と、一般式が[]で表される1
種以上の単量体とからなる共重合体の樹脂を染色
したことを特徴とする合成樹脂レンズの染色方
法。 (式中、Xはフツ素を除くハロゲン又は水素、Y
はフツ素を除くハロゲン又は水素、Rは水素又は
メチル基、mは1〜5の整数、nは0〜3の整数
を表す)
[Claims] 1. 0.5 to 50.0 g of ethyl benzoate or netyl salicylate or a mixture of both as a carrier, 0.2 to 20.0 g of an anionic surfactant, and 0.5 to 20.0 g of a disperse dye per 1 part of water. 1 whose general formula is represented by [ ] using a staining solution consisting of g.
More than one species of monomer and 1 whose general formula is represented by []
A method for dyeing synthetic resin lenses, characterized by dyeing a copolymer resin comprising at least one monomer. (In the formula, X is halogen or hydrogen excluding fluorine, Y
is a halogen or hydrogen excluding fluorine, R is hydrogen or a methyl group, m is an integer of 1 to 5, and n is an integer of 0 to 3)
JP57018639A 1982-02-08 1982-02-08 Dyeing of synthetic resin lens Granted JPS58136882A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP57018639A JPS58136882A (en) 1982-02-08 1982-02-08 Dyeing of synthetic resin lens

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP57018639A JPS58136882A (en) 1982-02-08 1982-02-08 Dyeing of synthetic resin lens

Publications (2)

Publication Number Publication Date
JPS58136882A JPS58136882A (en) 1983-08-15
JPH034671B2 true JPH034671B2 (en) 1991-01-23

Family

ID=11977169

Family Applications (1)

Application Number Title Priority Date Filing Date
JP57018639A Granted JPS58136882A (en) 1982-02-08 1982-02-08 Dyeing of synthetic resin lens

Country Status (1)

Country Link
JP (1) JPS58136882A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8630363D0 (en) * 1986-12-19 1987-01-28 Igel Int Ltd Coloured hydrogel objects
JP2606311B2 (en) * 1988-08-09 1997-04-30 東レ株式会社 Method for producing dyed high refractive index plastic lens
JP5040531B2 (en) * 2007-08-30 2012-10-03 セイコーエプソン株式会社 Plastic lens dyeing method

Also Published As

Publication number Publication date
JPS58136882A (en) 1983-08-15

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