JPH01197528A - Composition for lens of high refractive index - Google Patents

Composition for lens of high refractive index

Info

Publication number
JPH01197528A
JPH01197528A JP63019498A JP1949888A JPH01197528A JP H01197528 A JPH01197528 A JP H01197528A JP 63019498 A JP63019498 A JP 63019498A JP 1949888 A JP1949888 A JP 1949888A JP H01197528 A JPH01197528 A JP H01197528A
Authority
JP
Japan
Prior art keywords
composition
groups
refractive index
high refractive
thioglycolate
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
Application number
JP63019498A
Other languages
Japanese (ja)
Inventor
Takao Kawaki
川木 隆雄
Makoto Kobayashi
真 小林
Osamu Aoki
青木 脩
Yoko Yamazaki
山崎 葉子
Tatsuo Iwai
辰雄 岩井
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.)
Mitsubishi Gas Chemical Co Inc
Original Assignee
Mitsubishi Gas Chemical Co Inc
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 Mitsubishi Gas Chemical Co Inc filed Critical Mitsubishi Gas Chemical Co Inc
Priority to JP63019498A priority Critical patent/JPH01197528A/en
Publication of JPH01197528A publication Critical patent/JPH01197528A/en
Pending legal-status Critical Current

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Abstract

PURPOSE:To make it possible both to provide a resin having a high refractive index, a low specific gravity and excellent impact resistance after curing and to form a compsn. for a plastic lens having a good storage stability, by compounding a specified thiol compd. with divinylbenzene in a specified ratio. CONSTITUTION:This compsn. comprises divinylbenzene and a thiol compd. having two or more aliph. -SH groups in the molecule and the molar ratio of the total vinyl groups to the total -SH groups is in the range of 1 or larger and 10 or smaller. The thiol compd. is pref. one or more compd. selected from among trimethylolpropane tris(thioglycolate), trimethylolpropane tris(beta-thiopropiona te), pentaerythritol tetrakis(thioglycolate) and pentaerythritol tetrakis(beta- thiopropionate).

Description

【発明の詳細な説明】 (産業上の利用分野) 本発明は光学用材料、特に眼鏡用プラスチックレンズ用
等の光学レンズ材料として好適な高屈折率レンズ用組成
物に関するものである。
DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to an optical material, particularly a composition for a high refractive index lens suitable as an optical lens material such as a plastic lens for eyeglasses.

(従来の技術とその問題点) プラスチックレンズ用として実用化されている硬化型樹
脂の代表はポリ(ジエチレングリフールビス7リルカー
ボネート)であり、耐衝撃性が良く軽量かつ染色性に優
れているため視力矯正用眼鏡用のプラスチックレンズ用
樹脂として良く使われている。
(Conventional technology and its problems) Poly(diethylene glyfur bis-7-lyl carbonate) is a typical curable resin that has been put into practical use for plastic lenses, and it has good impact resistance, is lightweight, and has excellent dyeability. Therefore, it is often used as a resin for plastic lenses for vision correction glasses.

しかしポリ(ジエチレングリコールビスアリルカーボネ
ート)は屈折率が1.50と低い欠点を有し、充分な性
能とは言いがたい。
However, poly(diethylene glycol bisallyl carbonate) has the disadvantage of a low refractive index of 1.50, and cannot be said to have sufficient performance.

即ち眼鏡用レンズとしてはレンズの緑の厚木が薄くかつ
色収差が少ないことが望まれる。レンズの縁の厚みは屈
折率が高いほど薄くなり色収差はアツベ数が高いほど少
なくなる。
That is, as a lens for spectacles, it is desired that the green thickening of the lens be thin and that there be little chromatic aberration. The higher the refractive index, the thinner the edge of the lens becomes, and the higher the Abbe number, the smaller the chromatic aberration.

そのため屈折率がポリ(ジエチレレグリコールビス7リ
ルカーポネート)よりも充分に高イレンズ用樹脂が望ま
れている。
Therefore, a resin for lenses having a sufficiently higher refractive index than poly(diethyreglycol bis7lyl carbonate) is desired.

高屈折率レンズ用の樹脂としてブロム原子を含ムヒドロ
キシ化合物とインシアネートとの反応により得られる樹
脂(特開昭58−164615号公4fi)や11ε黄
原子を含むポリオール化合物とポリイソシアネートとの
反応により得られる樹脂(特開昭60−217229号
公報)ブロム原子を含む芳香族アクリル化合物からなる
樹脂(特開昭57−104901号公報)等、数多くの
提案がなされている。
As a resin for high refractive index lenses, a resin obtained by the reaction of a hydroxy compound containing a bromine atom with incyanate (JP-A-58-164615 4fi) and a reaction between a polyol compound containing an 11ε yellow atom and a polyisocyanate. A number of proposals have been made, including resins obtained by JP-A-60-217229 and resins made of aromatic acrylic compounds containing bromine atoms (JP-A-57-104901).

しかしながら、インシアネートを用いた場合は樹脂の硬
化前の保存安定性が悪く空気中の水分の影響を受けやす
い欠点があり、又ブロム原子を含む芳香族アクリル化合
物を用いた場合は樹脂の比重が大きくなる欠点がある。
However, when incyanate is used, the storage stability of the resin before curing is poor and it is easily affected by moisture in the air, and when an aromatic acrylic compound containing bromine atoms is used, the specific gravity of the resin is low. The disadvantage is that it gets bigger.

また、ジビニルベンゼンの重合物は公知の樹脂であるが
耐衝〃性が低く実用的でない。
Furthermore, although divinylbenzene polymers are known resins, they have low impact resistance and are not practical.

(問題点を解決するための手段) 本発明者等は硬化により高屈折率で、しかも比重が小さ
く、耐衝撃性に優れた樹脂を与え且つ組成物の保存安定
性が良いプラスチックレンズ用の組成物について検討し
た結果、本発明に到達したものである。
(Means for Solving the Problems) The present inventors have developed a composition for plastic lenses that can be cured to provide a resin with a high refractive index, low specific gravity, and excellent impact resistance, and which has good storage stability. As a result of studying the matter, the present invention was arrived at.

すなわち、本発明は、ジビニルベンゼンおよび分子中に
2個以上の脂肪族性−SH基を有するチオール化合物か
らなり、組成物中の全ビニル基/全−SH基のモル比が
1以上10以下の範囲である高屈折率レンズ用組成物で
ある。
That is, the present invention comprises divinylbenzene and a thiol compound having two or more aliphatic -SH groups in the molecule, and the molar ratio of total vinyl groups/total -SH groups in the composition is from 1 to 10. It is a composition for a high refractive index lens that has a range of .

本発明に於いて用いられるジビニルベンゼンは工業用途
のパラジビニルベンゼン、メタジビニルベンゼンあるい
はそれらの混合物が挙げられる。また分子中c2個以上
の脂肪族性−3H基を有するチオール化合物とは、1分
子中に−CH2SH,−CH3Iあるいは三C3H基を
2個以上含む化合物を示す。
The divinylbenzene used in the present invention includes industrially used para-divinylbenzene, meta-divinylbenzene, or a mixture thereof. The thiol compound having c2 or more aliphatic -3H groups in the molecule refers to a compound containing two or more -CH2SH, -CH3I or triC3H groups in one molecule.

例えば、エチレングリフールジチオグリコレート、エチ
レングリコールジチオプロピオネ−)、1.4−ブタン
ジオールジチオグリコレ−)、1.4−ブタンジオール
ジチオプロピオネート、トリメチロールプロパントリス
(β−チオグリコレート)、トリメチロールプロパント
リス(β−チオプロピオネート)、ペンタエリスリトー
ルテトラキズ(β−チオグリコレート)、ペンタエリス
リトールテトラキズ(β−チオプロピオネ−))、1,
2−ジメルカプトエタン、1.2.3−)リメルカプト
プロパン、1,4−ビス(メルカプトメチル)ベンゼン
、1,3゜5−トリス(メルカプトメチル)ベンゼン、
2−メチル−1,2−ジメルカプトプロパン等カ挙げら
れる。
For example, ethylene glycol dithioglycolate, ethylene glycol dithiopropione), 1,4-butanedioldithioglycolate), 1,4-butanediol dithiopropionate, trimethylolpropane tris(β-thioglycolate) ), trimethylolpropane tris (β-thiopropionate), pentaerythritol tetra-wound (β-thioglycolate), pentaerythritol tetra-wound (β-thiopropionone-)), 1,
2-dimercaptoethane, 1.2.3-)rimercaptopropane, 1,4-bis(mercaptomethyl)benzene, 1,3°5-tris(mercaptomethyl)benzene,
Examples include 2-methyl-1,2-dimercaptopropane.

特に好ましくは、トリメチロールプロパントリス(チオ
グリコレート)、トリメチロールプロパントリス(β−
チオプロピオネート)、ペンタエリスリトールテトラキ
ズ(チオグリコレート)、ペンタエリスリトールテトラ
キズ(β−チオプロピオネート)から選択されたチオー
ル化合物を挙げることができる。なおこれらのチオール
化合物は単独あるいは混合して使用しうる。
Particularly preferred are trimethylolpropane tris (thioglycolate), trimethylolpropane tris (β-
Mention may be made of the thiol compounds selected from thiol compounds such as thiopropionate), pentaerythritol tetrawound (thioglycolate), and pentaerythritol tetrawound (β-thiopropionate). Note that these thiol compounds can be used alone or in combination.

組成物中のジビニルベンゼンと分子中に2個以上の脂肪
族性−3H基を有するチオール化合物との配合割合は組
成物中の、全ビニル基/全−SH基のモル比が1以上1
0以下の範囲であるように配合するが、より好ましくは
2以上6以下の範囲で配合される。
The blending ratio of divinylbenzene and the thiol compound having two or more aliphatic -3H groups in the molecule in the composition is such that the molar ratio of total vinyl groups/total -SH groups in the composition is 1 or more and 1 or more.
It is blended so that it is in the range of 0 or less, and more preferably in the range of 2 or more and 6 or less.

前記の配合比以下の場合は組成物の硬化が不十分となり
硬化物の強度が不足する。また前記の配合比以上の場合
は得られる硬化物の光学的物性の特異性が失われ、且つ
強度が不足する。
If the blending ratio is less than the above-mentioned ratio, the composition will not be sufficiently cured and the strength of the cured product will be insufficient. If the mixing ratio exceeds the above range, the specificity of the optical properties of the resulting cured product will be lost and the strength will be insufficient.

本発明の組成物はラジカル重合開始剤を添加して重合、
硬化せしめ既述のレンズ等の光学用材料として使用され
るが、この場合使用されるラジカル重合開始剤は、加熱
あるいは紫外線や電子線によってラジカルを生成するも
のであれば使用可能であり、例えば過酸化ベンゾイル、
ジイソプロピルパーオキシカーボネート、アゾビスイン
ブチロニトリル等の熱重合触媒、ベンゾフェノン、ベン
ゾイン、ベンゾインメチルエーテル等の光重合触媒が挙
げられる。
The composition of the present invention is polymerized by adding a radical polymerization initiator,
The cured product is used as an optical material such as the above-mentioned lenses, but the radical polymerization initiator used in this case can be used as long as it generates radicals by heating, ultraviolet rays, or electron beams. benzoyl oxide,
Examples include thermal polymerization catalysts such as diisopropyl peroxycarbonate and azobisin butyronitrile, and photopolymerization catalysts such as benzophenone, benzoin and benzoin methyl ether.

ラジカル重合触媒の配合量は組成物の成分や硬化方法に
よって変化するので一概には決められないが、通常は組
成物総量に対して0.001%〜5%、好ましくはo、
oi%〜5にの範囲である6 尚、本組成物はラジカル反応性化合物、例えばスチレン
、エチルスチレン、クロースチレン、トリメチロールブ
ーバントリス(アクリレート)、′ペンタエリスリトー
ルテトラキズ(7クリレー))、)リメチーールプロパ
ントリス(β−チオグリコレート)等のビニル化合物で
希釈することができるがその場合、全ビニル基/全−S
H基のモル比は1以上10以下の範囲であることが必要
である。
The amount of the radical polymerization catalyst varies depending on the components of the composition and the curing method, so it cannot be determined unconditionally, but it is usually 0.001% to 5% based on the total amount of the composition, preferably o,
oi% to 5.6 The present composition may contain radically reactive compounds such as styrene, ethylstyrene, claustyrene, trimethylolbubantris (acrylate), 'pentaerythritol tetrakis (7cryl)), ) can be diluted with a vinyl compound such as rimethylpropane tris(β-thioglycolate), but in that case, all vinyl groups/all-S
The molar ratio of H groups needs to be in the range of 1 or more and 10 or less.

また、本発明の組成物に公知の酸化防止剤や紫外線吸収
剤あるいは重合禁止剤等の添加剤を加えて、得られる樹
脂の実用性向上を図ることはもちろん可能である。
Furthermore, it is of course possible to improve the practicality of the resulting resin by adding known additives such as antioxidants, ultraviolet absorbers, or polymerization inhibitors to the composition of the present invention.

本発明の組成物はその応用例の1つとして例えば次のよ
うにしてレンズ化することができる。
As one example of its application, the composition of the present invention can be made into a lens in the following manner.

すなわち組成物にラジカル重合開始剤を加えこれをガラ
スや金属製の型に注入し、加熱あるいは紫外線照射によ
って重合反応を進め、0.1〜24時間後に型から取り
外す。更に必要に応じてハードコート、反射防止、防曇
性等の表面処理を行う。
That is, a radical polymerization initiator is added to the composition, the mixture is poured into a glass or metal mold, the polymerization reaction is advanced by heating or ultraviolet irradiation, and the composition is removed from the mold after 0.1 to 24 hours. Furthermore, surface treatments such as hard coating, antireflection, and antifogging properties are performed as necessary.

(発明の効果) 本発明の組成物を重合硬化して得られるレンズは無色透
明、屈折率が高く、シかもアツベ数が高く、その上、比
重が小さく軽い、耐衝撃性が良い、耐熱性に優れる、研
磨性等の加工性に優れる、等の特徴がある。また組成物
の保存安定性が良い、等の特徴があるので光学材料とし
ての各種用途に使用でき、特に眼債用プラスチックレン
ズ用として好適である。
(Effects of the Invention) The lenses obtained by polymerizing and curing the composition of the present invention are colorless and transparent, have a high refractive index, a high stain count, and have a small specific gravity, are light, have good impact resistance, and are heat resistant. It has characteristics such as excellent polishability and processability such as polishability. Furthermore, since the composition has characteristics such as good storage stability, it can be used in various applications as an optical material, and is particularly suitable for use in plastic lenses for eye bonds.

(実施例) 以下、実施例及び比較例により本発明を更に詳しく説明
する。
(Examples) Hereinafter, the present invention will be explained in more detail with reference to Examples and Comparative Examples.

なお、硬化物の耐熱性、耐衝撃性はそれぞれ次のような
方法にて評価を行った。
The heat resistance and impact resistance of the cured product were evaluated using the following methods.

耐熱性 :硬化物のビカット熱軟化温度(荷重IKf)
が120℃以上の場合を良好とする。
Heat resistance: Vicat heat softening temperature of cured product (load IKf)
A case where the temperature is 120°C or higher is considered good.

耐衝撃性:硬化物(60朋メX2,5fim厚みの円板
)に1.27mの高さから30gの鉄球を落とし割れな
い場合を良好とする。
Impact resistance: Good if a 30g iron ball is dropped onto the cured product (disc of 60mm x 2.5mm thick) from a height of 1.27m and no cracking occurs.

実施例 1 メタジビニルベンゼン 60部、ペンタエリスリトール
テトラキズ(β−チオプロピオネート) 40部、から
なる組成物に重合開始剤としてバーブチル0(t−ブチ
ルパーオキシ(2−エチルヘキサノエイ)))  0.
5部を均一に混合し、2枚のガラスとゴム製ガスケット
で構成された母型の中に注入して、50℃から55℃ま
で10時間、55℃から65℃まで5時間、65℃から
75℃まで2時間、75℃から100℃まで3時間、そ
れぞれ直線的に昇温後、100℃で1時間保持して重合
硬化を行った。
Example 1 A composition consisting of 60 parts of metadivinylbenzene and 40 parts of pentaerythritol tetrakiz (β-thiopropionate) was added with barbutyl 0 (t-butylperoxy (2-ethylhexanoei)) as a polymerization initiator. 0.
5 parts were uniformly mixed, poured into a mold made of two pieces of glass and a rubber gasket, and heated from 50°C to 55°C for 10 hours, from 55°C to 65°C for 5 hours, and from 65°C to The temperature was linearly raised to 75°C for 2 hours and from 75°C to 100°C for 3 hours, and then held at 100°C for 1 hour to perform polymerization and curing.

なお、組成物中の全ビニル基/全−SH基のモル比は2
.8であった。
The molar ratio of all vinyl groups/all -SH groups in the composition is 2.
.. It was 8.

また、組成物を室温に3時間放置しても粘度の上昇は見
られなかった。
Furthermore, no increase in viscosity was observed even when the composition was left at room temperature for 3 hours.

得らhた硬化物は無色透明であり、アツベ屈20℃ 折計により測定した屈折率(ND)は1゜609、アツ
ベ数は32と高屈折率かつ高アツベ数の良好な光学的特
性を有していた。
The obtained cured product is colorless and transparent, has a refractive index (ND) of 1°609 measured using a refractometer at 20°C, and has good optical properties with a high refractive index and a high Atsbe number of 32. had.

また、比重は1.19と軽く、耐熱性及び耐衝撃性は良
好であり、レンズ特に眼ψ用レンズとして優れたもので
あった。
In addition, the specific gravity was light at 1.19, and the heat resistance and impact resistance were good, making it an excellent lens, especially as an eye lens.

実施例、2〜6及び比較例1 実施例1と同様に重合開始剤としてパーブチル0を用い
、表1の組成物を重合硬化した。得られた硬化物は無色
透明であった。測定した物性値を表1に示す。
Examples, 2 to 6 and Comparative Example 1 Similarly to Example 1, the compositions shown in Table 1 were polymerized and cured using Perbutyl 0 as a polymerization initiator. The obtained cured product was colorless and transparent. Table 1 shows the measured physical property values.

なお表中の略号は次の化合物を示す。The abbreviations in the table indicate the following compounds.

mDVB:メタシヒニルベンゼン RDvB:市販試薬ジビニルベンゼン (メタ、ハラ体及びエチルビニルベ ンゼン30?(を含む混合物) TMTP : )リメチロールプロパントリス(β−チ
オプロピオネート) PETP :ペンタエリスリトールテトラキズ(β−チ
オプロピオネート) PETG:ペンタエリスリトールテトラキズ(β−チオ
グリフレート) DME  :1,2−ジメルカプトエタンBMMB :
 1.4−ビス(メルカプトメチル)ベンゼン
mDVB: Metacyhinylbenzene RDvB: Commercially available reagent divinylbenzene (mixture containing meta, hala and ethylvinylbenzene 30?) TMTP: ) Limethylolpropane tris (β-thiopropionate) PETP: Pentaerythritol tetrakis ( β-Thiopropionate) PETG: Pentaerythritol Tetrakis (β-Thioglyflate) DME: 1,2-dimercaptoethane BMMB:
1.4-bis(mercaptomethyl)benzene

Claims (2)

【特許請求の範囲】[Claims] (1)ジビニルベンゼンおよび1分子中に2個以上の脂
肪族性−SH基を有するチオール化合物から成る組成物
であつて組成物中の全ビニル基/全−SH基のモル比が
1以上10以下の範囲である高屈折率レンズ用組成物。
(1) A composition comprising divinylbenzene and a thiol compound having two or more aliphatic -SH groups in one molecule, wherein the molar ratio of total vinyl groups/total -SH groups in the composition is 1 or more and 10 or more. A composition for a high refractive index lens having the following range.
(2)チオール化合物が、トリメチロールプロパントリ
ス(チオグリコレート)、トリメチロールプロパントリ
ス(β−チオプロピオネート)、ペンタエリスリトール
テトラキズ(チオグリコレート)、ペンタエリスリトー
ルテトラキズ(β−チオプロピオネート)から選択され
たものである請求項1記載の高屈折率レンズ用組成物。
(2) Thiol compounds include trimethylolpropane tris (thioglycolate), trimethylolpropane tris (β-thiopropionate), pentaerythritol tetra-wound (thioglycolate), and pentaerythritol tetra-wound (β-thiopropionate). 2. The high refractive index lens composition according to claim 1, wherein the composition is selected from the group consisting of:
JP63019498A 1988-02-01 1988-02-01 Composition for lens of high refractive index Pending JPH01197528A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP63019498A JPH01197528A (en) 1988-02-01 1988-02-01 Composition for lens of high refractive index

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP63019498A JPH01197528A (en) 1988-02-01 1988-02-01 Composition for lens of high refractive index

Publications (1)

Publication Number Publication Date
JPH01197528A true JPH01197528A (en) 1989-08-09

Family

ID=12001035

Family Applications (1)

Application Number Title Priority Date Filing Date
JP63019498A Pending JPH01197528A (en) 1988-02-01 1988-02-01 Composition for lens of high refractive index

Country Status (1)

Country Link
JP (1) JPH01197528A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01315701A (en) * 1988-03-08 1989-12-20 Toray Ind Inc Plastic lens base material and its production
JPH02289622A (en) * 1989-01-20 1990-11-29 Toray Ind Inc Optical resin
US5288844A (en) * 1991-08-01 1994-02-22 Teruo Sakagami High-refractive index plastic optical material
WO1998038146A2 (en) * 1997-02-14 1998-09-03 Sola International Holdings Ltd. Cross-linkable polymeric composition
US5917006A (en) * 1998-01-16 1999-06-29 Ppg Industries Ohio, Inc. Optical resin composition
WO1999032907A1 (en) * 1997-12-22 1999-07-01 Kureha Kagaku Kogyo Kabushiki Kaisha Synthetic resin lens and process for producing the same
US6573348B2 (en) 2000-04-13 2003-06-03 Daiso Co. Ltd Curable resin composition
US6872333B2 (en) * 2002-02-07 2005-03-29 Mitsubishi Gas Chemical Company, Ltd. Enic compounds, sulfur-containing polyenic compound, sulfur-containing polythiol compound, high refractive index photocurable composition and cured product thereof

Cited By (11)

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JPH01315701A (en) * 1988-03-08 1989-12-20 Toray Ind Inc Plastic lens base material and its production
JPH02289622A (en) * 1989-01-20 1990-11-29 Toray Ind Inc Optical resin
US5288844A (en) * 1991-08-01 1994-02-22 Teruo Sakagami High-refractive index plastic optical material
WO1998038146A2 (en) * 1997-02-14 1998-09-03 Sola International Holdings Ltd. Cross-linkable polymeric composition
WO1998038146A3 (en) * 1997-02-14 2000-04-06 Sola Int Holdings Cross-linkable polymeric composition
US6391983B1 (en) 1997-02-14 2002-05-21 Sola International Holdings, Ltd. Casting composition of aromatic polyvinyl monomer, polythiol and epoxy strain reducer
WO1999032907A1 (en) * 1997-12-22 1999-07-01 Kureha Kagaku Kogyo Kabushiki Kaisha Synthetic resin lens and process for producing the same
US5917006A (en) * 1998-01-16 1999-06-29 Ppg Industries Ohio, Inc. Optical resin composition
US6573348B2 (en) 2000-04-13 2003-06-03 Daiso Co. Ltd Curable resin composition
US6872333B2 (en) * 2002-02-07 2005-03-29 Mitsubishi Gas Chemical Company, Ltd. Enic compounds, sulfur-containing polyenic compound, sulfur-containing polythiol compound, high refractive index photocurable composition and cured product thereof
US7026372B2 (en) 2002-02-07 2006-04-11 Mitsubishi Gas Chemical Company, Inc. Enic compounds, sulfur-containing polyenic compound, sulfur-containing polythiol compound, high refractive index photocurable composition and cured product thereof

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