JP5011004B2 - 赤外線吸収性眼鏡用レンズおよびその製造方法 - Google Patents
赤外線吸収性眼鏡用レンズおよびその製造方法 Download PDFInfo
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- JP5011004B2 JP5011004B2 JP2007171580A JP2007171580A JP5011004B2 JP 5011004 B2 JP5011004 B2 JP 5011004B2 JP 2007171580 A JP2007171580 A JP 2007171580A JP 2007171580 A JP2007171580 A JP 2007171580A JP 5011004 B2 JP5011004 B2 JP 5011004B2
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Images
Classifications
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- C08G18/6677—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
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- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
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- C—CHEMISTRY; METALLURGY
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
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- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
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- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/12—Polarisers
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- G—PHYSICS
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Description
チレンビス(シクロへキシルイソシアネート)又はイソホロンジイソシアネートが好ましい。
アジペート、1,6−へキサンジオールアジペートが好ましい。
(1) N,N,N´,N´−テトラキス(p-置換フェニル)-p−フェニレンジアミン類、ベンジジン類及びそれらのアルミニウム塩、ジイモニウム塩からなる赤外線吸収剤。
(2) N,N,N´,N´−テトラアリールキノンジイモニウム塩類。
(3) ビス−(p-ジアルキルアミノフェニル)〔N,N-ビス(p-ジアルキルアミノフェニル
)p-アミノフェニル〕アミニウム塩。
(1) 2−ヒドロキシ−4−n−オクトキシベンゾフェノン
(2) 4−ドデシロキシ−2−ヒドロキシベンゾフェノン
(3) 2−2´−ヒドロキシ−4−メトキシベンゾフェノン
染料の種類としては、直接染料、酸性染料、塩基性染料、硫化染料、分散染料、油溶染料などがあるが、堅牢性の優れた染料を使用する事が望ましい。
また、紫外線吸収剤を添加することにより赤外線吸収剤の屋外使用での耐久性が向上する。
赤外線波長(780nm〜2500nm)については、平均透過率として、10%未満、好ましくは1%未満が適している。
但し、溶接作業などにおいて使用される遮光保護具用については、規定される規格に基づくので、この限りではない。
(1)紫外線UV−B,Cによる角膜、結膜への障害
(2)紫外線UV−Aによる水晶体への障害
(3)青色光による網膜への光化学的障害
(4)可視光線、近赤外線による角膜、水晶体への障害
(5)近・中赤外線による角膜、水晶体への障害
製造例1:温度計、攪拌機、窒素シール管を備えた500mlセパラブルフラスコに、平均分子量1014のポリオキシテトラメチレングリコール(保土谷化学工業製:PTG−1000N)200部をとり、窒素気流中で攪拌しながら加熱し、100〜110℃/3〜5mmHgの減圧下で1時間脱水した。脱水後4,4´−メチレン−ビス(シクロへキシルイソシアネート)(住友バイエルウレタン製:デスモジュールW)170部を添加し、120〜130℃で2時間反応してプレポリマーを製造した。得られたプレポリマーは無色透明液体であり、NCO含量9.9%、粘度8600mPa・s/30℃,750mPa・s/60℃であった。このプレポリマーをAとする。
ネート)を190部添加し、120〜130℃で2時間反応してプレポリマーを得た。得られたプレポリマーはほぼ無色透明の液体であり、NCO含量10.1%、粘度8000mPa・s/30℃、920mPa・s/60℃であった。このプレポリマーをBとする。
製造例1で得られたプレポリマーAの100重量部を70℃に加熱してから、赤外線吸収剤(IR剤)のジイモニウム系化合物(日本化薬社製:IRG−022)を0.10重量部添加し混合した後、120℃で溶融した4,4´−メチレン−ビス(2−クロロアニリン)31.4重量部と脱泡混合した。この混合物を100℃で予備加熱したモールドに注入し、100℃で24時間加熱硬化し、眼鏡用レンズ(偏光膜は不使用)を製造した。この時の混合モル比(NCO/NH2)は1.0であり、得られた眼鏡レンズ(レンズ厚さ約2.6mm)の近赤外分光チャートを図1に示した。
実施例1において、レッド系色調(コパー30)の偏光膜をサンドイッチして注型成形し、赤外線吸収剤のジイモニウム系化合物(日本化薬社製:IRG−022)を0.13重量部添加したこと以外は全く同様にして偏光レンズを製造した。得られた偏光眼鏡レンズ(レンズ厚さ約2.0mm)の近赤外分光チャートを図2に示した。
実施例1において、レッド系色調(コパー30)の偏光膜をサンドイッチして注型成形し、赤外線吸収剤のジイモニウム系化合物(日本化薬社製:IRG−022)を0.15重量部添加したこと以外は全く同様にして偏光レンズを製造した。得られた偏光眼鏡レンズ(レンズ厚さ約1.7mm)の近赤外分光チャートを図3に示した。
実施例1において、グレー系色調(TG−15)の偏光膜をサンドイッチして注型成形し、赤外線吸収剤のジイモニウム系化合物(日本化薬社製:IRG−022)を0.10重量部添加したこと以外は全く同様にして偏光レンズを製造した。得られた偏光眼鏡レンズ(レンズ厚さ約2.0mm)の近赤外分光チャートを図4に示した。
実施例1において、赤外線吸収剤のジイモニウム系化合物(日本化薬社製:IRG−022)を0.20重量部添加したこと以外は全く同様にしてゴーグルの透視性保護面部分(眼鏡レンズ部分)に用いるシートを製造した。得られたゴーグル用シート(シート厚さ1.0mm)の近赤外分光チャートを図5に示した。
実施例5において、レッド系色調(コパー50)の偏光膜をサンドイッチして注型成形したこと以外は全く同様にしてゴーグル用シートを製造した。得られたゴーグル用シート(シート厚さ1.0mm)の近赤外分光チャートを図6に示した。
製造例1で得られたプレポリマーAの100重量部を70℃に加熱してから、赤外線吸収剤(IR剤)のジイモニウム系化合物(日本化薬社製:IRG−022)を0.10重量部添加し混合した後、120℃で溶融した4,4´メチレン-ビス(2,6-ジエチルアニリン)36.5重量部と脱泡混合した。この混合物を100℃で予備加熱したモールドに注入し、数分のポットライフに応じて速やかに成型を完了させ、100℃で24時間加熱硬化し、眼鏡用レンズ(偏光膜は不使用)を製造した。得られた眼鏡レンズ(レンズ厚さ約2.0mm)の近赤外分光チャートを図7に示した。
製造例1で得られたプレポリマーAの100重量部を70℃に加熱してから、赤外線吸収剤(IR剤)のジイモニウム系化合物(日本化薬社製:IRG−022)を0.10重量部添加し混合した後、120℃で溶融した4,4´メチレン-ビス(3-クロロ-2,6-ジエチルアニリン)44.6重量部と脱泡混合した。この混合物を100℃で予備加熱したモールドに注入する際、レッド系色調(コパー30)の偏光膜をサンドイッチして迅速に注型成形し、100℃で24時間加熱硬化し、眼鏡用偏光レンズを製造した。得られた眼鏡用偏光レンズ(レンズ厚さ約2.2mm)の近赤外分光チャートを図8に示した。
母材の樹脂として高屈折率樹脂(三井化学製:チオウレタン系樹脂MR−7、屈折率1.67)100重量部に対して、赤外線吸収剤のジイモニウム系化合物(日本化薬社製:IRG−022)を0.13重量部添加し、レッド系色調(コパ−15)の偏光膜をサンドイッチして注型成形して偏光レンズを製造した。得られた偏光眼鏡レンズ(レンズ厚さ約2.4mm)の近赤外分光チャートを図9に示した。
母材の樹脂としてアリルジグリコールカーボネート(CR−39)100重量部に対して、赤外線吸収剤のジイモニウム系化合物(日本化薬社製:IRG−022)を0.13重量部添加し、レッド系色調(コパー30)の偏光膜をサンドイッチして注型成形して偏光レンズを製造した。得られた偏光眼鏡レンズ(レンズ厚さ約2.0mm)の近赤外分光チャートを図10に示した。
実施例1において、レッド系色調(コパー30)の偏光膜をサンドイッチして注型成形し、赤外線吸収剤を添加しなかったこと以外は全く同様にして偏光レンズを製造した。得られた偏光眼鏡レンズ(レンズ厚さ約2.0mm)の近赤外分光チャートを図11に示した。
比較例1において、母材の樹脂として同じ高屈折率樹脂(三井化学製:チオウレタン系樹脂MR−7、屈折率1.67)を用い、赤外線吸収剤を添加せず、偏光膜も用いずに注型成形して眼鏡レンズを製造した。得られた眼鏡レンズ(レンズ厚さ約2.3mm)の近赤外分光チャートを図12に示した。
母材の樹脂として高屈折率樹脂(三井化学製:チオウレタン系樹脂MR−7、屈折率1.67)100重量部に対して、赤外線吸収剤のジイモニウム系化合物(日本化薬社製:IRG−022)を0.15重量部添加し、偏光膜を用いずに注型成形して眼鏡レンズを製造した。得られた眼鏡レンズ(レンズ厚さ約2.3mm)の近赤外分光チャートを図13に示した。
比較例2と同様に、母材の樹脂としてアリルジグリコールカーボネート(CR−39)を採用し、赤外線吸収剤は添加せず、偏光膜も使用せずに注型成形して眼鏡レンズを製造した。得られた眼鏡レンズ(レンズ厚さ約2.0mm)の近赤外分光チャートを図14に示した。
比較例2と同様に、母材の樹脂としてアリルジグリコールカーボネート(CR−39)100重量部に対して、赤外線吸収剤のジイモニウム系化合物(日本化薬社製:IRG−022)を0.13重量部添加し、偏光膜を使用せずに注型成形して眼鏡レンズを製造した。得られた眼鏡レンズ(レンズ厚さ約2.0mm)の近赤外分光チャートを図15に示した。
Claims (9)
- ポリイソシアネートとポリヒドロキシ化合物を反応させたプレポリマーと、芳香族ポリアミンとが、過酸化物系添加剤を添加せずに付加重合反応してなるポリウレタン樹脂組成物に、波長780〜2500nmの範囲に渡って赤外線を吸収する赤外線吸収色素を前記波長範囲での赤外線の透過率の平均が30%以下に抑制できるように配合した樹脂組成物からなる赤外線吸収性眼鏡用レンズ。
- 赤外線吸収色素が、下記の(1)、(2)および(3)からなる群から選ばれる赤外線吸収色素である請求項1に記載の赤外線吸収性眼鏡用レンズ。
記
(1) N,N,N´,N´−テトラキス(p−置換フェニル)−p−フェニレンジアミン類、同ベンジジン類、それらのアルミニウム塩またはジイモニウム塩
(2) N,N,N´,N´−テトラアリールキノンジイモニウム塩類
(3) ビス−(p−ジアルキルアミノフェニル)〔N,N−ビス(p−ジアルキルアミノフェニル)p−アミノフェニル〕アミニウム塩 - 波長400nm以下の紫外線を吸収する紫外線吸収剤が配合されている請求項1または2に記載の赤外線吸収性眼鏡用レンズ。
- ポリイソシアネートが、4,4´−メチレン−ビス(シクロヘキシルイソシアネート)またはイソホロンジイソシアネートである請求項1〜3のいずれかに記載の赤外線吸収性眼鏡用レンズ。
- ポリヒドロキシ化合物が、平均分子量700〜1200のポリエーテルジオールもしくはポリエステルジオールまたはこれらの混合物である請求項1〜3のいずれかに記載の赤外線吸収性眼鏡用レンズ。
- ポリイソシアネートおよびポリヒドロキシ化合物の反応モル比(NCO/OH)が、2.5〜4.0でありかつ生成するポリウレタンプレポリマーのNCO含量が7.0〜14.0%となるようにポリイソシアネートとポリヒドロキシ化合物とを配合した請求項1〜3のいずれかに記載の赤外線吸収性眼鏡用レンズ。
- 眼鏡用レンズが、透明レンズ、着色レンズまたは偏光レンズである請求項1〜3のいずれかに記載の赤外線吸収性眼鏡用レンズ。
- 眼鏡用レンズが、サングラス用レンズ、偏光眼鏡用レンズまたはゴーグル用シールドレンズである請求項1〜3のいずれかに記載の赤外線吸収性眼鏡用レンズ。
- ポリイソシアネートおよびポリヒドロキシ化合物をこれらの反応モル比(NCO/OH)が2.5〜4.0となるように過酸化物系添加剤を添加せずに配合し、得られたNCO含量7.0〜14.0%のポリウレタンプレポリマーと芳香族ポリアミンを反応モル比(NCO/NH2 )が1.10〜0.90となるように配合すると共に、波長780〜2500nmの範囲に渡って赤外線を吸収する赤外線吸収色素を前記波長範囲での赤外線の透過率の平均が30%以下に抑制できるように配合し、これを注型すると共に60〜140℃で硬化することからなる請求項1に記載のポリウレタン樹脂製の赤外線吸収性眼鏡用レンズの製造方法。
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007171580A JP5011004B2 (ja) | 2007-04-13 | 2007-06-29 | 赤外線吸収性眼鏡用レンズおよびその製造方法 |
CN2008800114081A CN101652700B (zh) | 2007-04-13 | 2008-04-09 | 红外线吸收性眼镜用透镜及其制造方法 |
US12/450,692 US9175128B2 (en) | 2007-04-13 | 2008-04-09 | Infrared absorbing spectacle lens and method for producing such lens |
KR1020097020048A KR20100014582A (ko) | 2007-04-13 | 2008-04-09 | 적외선 흡수성 안경용 렌즈 및 그의 제조 방법 |
EP08740103.0A EP2138887B1 (en) | 2007-04-13 | 2008-04-09 | Infrared ray-absorbable eyeglass lens, and method for production thereof |
PCT/JP2008/057000 WO2008133008A1 (ja) | 2007-04-13 | 2008-04-09 | 赤外線吸収性眼鏡用レンズおよびその製造方法 |
AU2008245205A AU2008245205B9 (en) | 2007-04-13 | 2008-04-09 | Infrared ray-absorbable eyeglass lens, and method for production thereof |
TW097113399A TWI413650B (zh) | 2007-04-13 | 2008-04-11 | 紅外線吸收性眼鏡用透鏡及其製造方法 |
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JP2007171580A JP5011004B2 (ja) | 2007-04-13 | 2007-06-29 | 赤外線吸収性眼鏡用レンズおよびその製造方法 |
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EP (1) | EP2138887B1 (ja) |
JP (1) | JP5011004B2 (ja) |
KR (1) | KR20100014582A (ja) |
CN (1) | CN101652700B (ja) |
AU (1) | AU2008245205B9 (ja) |
TW (1) | TWI413650B (ja) |
WO (1) | WO2008133008A1 (ja) |
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JP5650963B2 (ja) * | 2010-09-13 | 2015-01-07 | タレックス光学工業株式会社 | 保護眼鏡用遮光レンズ |
US9778490B2 (en) | 2011-11-04 | 2017-10-03 | Spy Optic Inc. | Therapeutic eyewear |
KR20140076396A (ko) * | 2012-12-12 | 2014-06-20 | 엘지이노텍 주식회사 | 촬상 렌즈 |
WO2015080160A1 (ja) | 2013-11-26 | 2015-06-04 | ホヤ レンズ タイランド リミテッド | 眼鏡レンズ |
JP2015118122A (ja) * | 2013-12-16 | 2015-06-25 | 東海光学株式会社 | 眼鏡レンズ及び眼鏡 |
WO2016010593A1 (en) * | 2014-07-16 | 2016-01-21 | Eye Ojo Corporation | Methods and system for manufacturing infrared (ir) absorbing lens |
US10611106B2 (en) | 2015-02-15 | 2020-04-07 | Roger Wen Yi Hsu | Methods and systems for making an optical functional film |
US20160238859A1 (en) * | 2015-02-15 | 2016-08-18 | Roger Wen Yi Hsu | Methods And Systems For Making An Optical Functional Film |
JP2018529829A (ja) * | 2015-07-13 | 2018-10-11 | ケーエス ラボラトリーズ カンパニー リミテッドKs Laboratories Co., Ltd. | 電磁波遮断用光学組成物及びそれを用いた光学レンズの製造方法 |
JP6570452B2 (ja) * | 2016-01-22 | 2019-09-04 | タレックス光学工業株式会社 | 眼鏡用偏光レンズ |
JP6563116B2 (ja) * | 2016-03-29 | 2019-08-21 | 富士フイルム株式会社 | 保護シート、画像表示装置、眼鏡レンズおよび眼鏡 |
US11073638B2 (en) * | 2016-09-07 | 2021-07-27 | Largan Precision Co., Ltd. | Optical image lens assembly and plastic material thereof, image capturing apparatus and electronic device |
US10890699B2 (en) | 2016-09-07 | 2021-01-12 | Largan Precision Co., Ltd. | Optical image lens assembly, image capturing apparatus and electronic device |
EP3318920B1 (en) * | 2016-11-04 | 2022-07-06 | Essilor International | Near infrared light-cutting optical articles with low residual color |
JP7048508B2 (ja) * | 2016-11-14 | 2022-04-05 | 日本化薬株式会社 | 赤外波長域用染料系偏光板 |
KR101831889B1 (ko) * | 2017-02-03 | 2018-02-26 | 에스케이씨 주식회사 | 플라스틱 렌즈용 폴리티올 조성물 |
JP7187780B2 (ja) * | 2018-02-16 | 2022-12-13 | 住友ベークライト株式会社 | 光学シートおよび光学部品 |
CN108594470B (zh) * | 2018-05-08 | 2020-06-02 | 江苏康耐特光学有限公司 | 一种多功能树脂镜片及其制备方法 |
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CN115698115A (zh) * | 2020-06-04 | 2023-02-03 | 依视路国际公司 | 用于具有1.54-1.58的折射率的光学材料的可聚合组合物和聚合物组合物、眼科镜片以及制造方法 |
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2007
- 2007-06-29 JP JP2007171580A patent/JP5011004B2/ja not_active Expired - Fee Related
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2008
- 2008-04-09 CN CN2008800114081A patent/CN101652700B/zh not_active Expired - Fee Related
- 2008-04-09 AU AU2008245205A patent/AU2008245205B9/en not_active Ceased
- 2008-04-09 EP EP08740103.0A patent/EP2138887B1/en not_active Not-in-force
- 2008-04-09 WO PCT/JP2008/057000 patent/WO2008133008A1/ja active Application Filing
- 2008-04-09 US US12/450,692 patent/US9175128B2/en not_active Expired - Fee Related
- 2008-04-09 KR KR1020097020048A patent/KR20100014582A/ko not_active Application Discontinuation
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Also Published As
Publication number | Publication date |
---|---|
CN101652700A (zh) | 2010-02-17 |
KR20100014582A (ko) | 2010-02-10 |
CN101652700B (zh) | 2011-12-07 |
TWI413650B (zh) | 2013-11-01 |
EP2138887B1 (en) | 2013-09-25 |
US9175128B2 (en) | 2015-11-03 |
AU2008245205B9 (en) | 2014-02-06 |
EP2138887A4 (en) | 2012-02-15 |
US20100118263A1 (en) | 2010-05-13 |
EP2138887A1 (en) | 2009-12-30 |
TW200912426A (en) | 2009-03-16 |
AU2008245205B2 (en) | 2013-07-25 |
JP2008281973A (ja) | 2008-11-20 |
AU2008245205A1 (en) | 2008-11-06 |
WO2008133008A1 (ja) | 2008-11-06 |
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