JP2023116551A - カプセル封入された光吸収剤を含む眼鏡用レンズの製造のための組成物 - Google Patents
カプセル封入された光吸収剤を含む眼鏡用レンズの製造のための組成物 Download PDFInfo
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000005649 substituted arylene group Chemical group 0.000 description 1
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- FDJUBNCEVCSIAV-UHFFFAOYSA-N tetrakis(o-aminophenyl)porphyrin Chemical compound NC1=CC=CC=C1C(C1=CC=C(N1)C(C=1C(=CC=CC=1)N)=C1C=CC(=N1)C(C=1C(=CC=CC=1)N)=C1C=CC(N1)=C1C=2C(=CC=CC=2)N)=C2N=C1C=C2 FDJUBNCEVCSIAV-UHFFFAOYSA-N 0.000 description 1
- KBIOUJDBIXSYJT-UHFFFAOYSA-N tetramesitylporphyrin Chemical compound CC1=CC(C)=CC(C)=C1C(C1=CC=C(N1)C(C=1C(=CC(C)=CC=1C)C)=C1C=CC(=N1)C(C=1C(=CC(C)=CC=1C)C)=C1C=CC(N1)=C1C=2C(=CC(C)=CC=2C)C)=C2N=C1C=C2 KBIOUJDBIXSYJT-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical class C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005068 thioepoxy group Chemical group S(O*)* 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 239000001775 zeaxanthin Substances 0.000 description 1
- 229940043269 zeaxanthin Drugs 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
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Abstract
Description
a)モノマー又はオリゴマーの重合を開始するための触媒の存在下で、少なくとも1種のアリル又は非アリル系のモノマー又はオリゴマーを重合することによって得られるマトリックス、
b)前記マトリックス中に分散されているナノ粒子の中に含まれる少なくとも1種の光吸収剤、
c)少なくとも1種の紫外線吸収剤、
を含む眼鏡用レンズであって:
厚さ2mmの眼鏡用レンズの光透過率が280~400nmの範囲の各光波長で1%未満であり、430nmの波長を有する光では65%超である、眼鏡用レンズである。
a)マトリックスを調製することができるモノマー又はオリゴマーを準備する工程;
b)モノマー又はオリゴマーの中に分散可能な粉末の形態か、モノマー又はオリゴマーの中に分散可能な液体中のナノ粒子の分散液の形態で、ナノ粒子の中に含まれる光吸収剤を調製する工程;
c)前記モノマー又はオリゴマーの重合を開始するための触媒を準備する工程;
d)紫外線吸収剤を準備する工程;
e)ナノ粒子が分散されている重合性液体組成物を得るために、モノマー又はオリゴマーと、ナノ粒子と、触媒と、紫外線吸収剤とを混合する工程;
e)任意選択的に重合性液体組成物を基材上に堆積させる工程;
f)重合性液体組成物を硬化させる工程;
を含む、眼鏡用レンズの作製方法である。
・ アルキル(メタ)アクリレート、特には
-アダマンチン、ノルボルネン、イソボルネン、シクロペンタジエン、又はジシクロペンタジエンから誘導された(メタ)アクリレート、
-メチル(メタ)アクリレート及びエチル(メタ)アクリレートなどのC1~C4アルキル(メタ)アクリレート;
・ ベンジル(メタ)アクリレート、フェノキシ(メタ)アクリレート、又はフルオレン(メタ)アクリレートなどの芳香族(メタ)アクリレート;
・ ビスフェノールから、特にはビスフェノールAから誘導される(メタ)アクリレート;
・ ポリエトキシル化ビスフェノレートジ(メタ)アクリレート、ポリエトキシル化フェノール(メタ)アクリレートなどのポリアルコキシル化芳香族(メタ)アクリレート;
・ ポリチオ(メタ)アクリレート;
・ アルキル(メタ)アクリル酸とポリオール又はエポキシとのエステル化生成物;
・ 並びにこれらの混合物。
モノマー又はオリゴマーがアリル型である場合、本発明によるマトリックスを生成するために使用される重合性組成物中の前記アリルモノマー又はオリゴマーの量は、組成物の総重量を基準として、20~99重量%、特には50~99重量%、より具体的には80~98重量%、更に具体的には90~97重量%であってもよい。特に、マトリックスを生成するために使用される重合性組成物は、組成物の総重量を基準として、20~99重量%、特には50~99重量%、より具体的には80~98重量%、更に具体的には90~97重量%のジエチレングリコールビス(アリルカーボネート)、ジエチレングリコールビス(アリルカーボネート)のオリゴマー、又はこれらの混合物を含有していてもよい。別の実施形態では、マトリックスを生成するために使用される重合性組成物は、組成物の総重量を基準として、20~40重量%の、ジエチレングリコールビス(アリルカーボネート)、ジエチレングリコールビス(アリルカーボネート)のオリゴマー、又はこれらの混合物と、組成物の総重量を基準として、40~80重量%の、ジアリルフタレート、イソジアリルイソフタレート、ジアリルテレフタレート、又はこれらの混合物を含有していてもよい。
モノマー又はオリゴマーが(メタ)アクリル型のものである場合、本発明によるマトリックスを生成するために使用される重合性組成物中の前記(メタ)アクリルモノマー又はオリゴマーの量は、組成物の総重量を基準として、20~99重量%、特には50~99重量%、より具体的には80~98重量%、更に具体的には90~97重量%である。
組成物に含まれる紫外線吸収剤は、可視光で残留吸収を示すように選択される。実際、これらの紫外線吸収剤は、UV-A範囲(315~380nm)に主な吸収帯を有しているものの、HEV紫青色光における吸収は完全には無視できない。したがって、これらの紫外線吸収剤は、紫外光からの優れた保護と一部のHEV紫青色光の吸収を同時に提供する。
吸光度=log(I0/Isample)
(式中、Aは二価の基であり、R1はクロロ基であり、R2基は同じ又は異なる一価の基であり、nは1~3の範囲の整数であり、R3は直鎖又は分岐の置換又は無置換のアルキル又はアリール基である)。ただし、クロロベンゾトリアゾール化合物は、アリル、アクリル、及びメタクリル部位から選択される重合性基を含まない。
であり、式中、R1は共鳴基であり、R2基は、同じ又は異なる一価の基であり、nは0又は1の整数であり、R3基は同じ又は異なる一価の基であり、mは0~2の範囲の整数である。
本発明による眼鏡用レンズ中に分散されているナノ粒子に含まれる光吸収剤は、紫外線、可視光、及び/又は赤外光を吸収することができる化合物である。
本発明によれば、光吸収剤は、本発明による組成物中に分散されているナノ粒子の中にカプセル封入される。すなわち、光吸収剤は前記ナノ粒子の中に含まれるかグラフト化される。
上記の眼鏡用レンズの作製を行うための方法は:
a)マトリックスを調製することができるモノマー又はオリゴマーを準備する工程;
b)モノマー又はオリゴマーの中に分散可能な粉末の形態であるか、モノマー又はオリゴマーの中に分散可能な液体中のナノ粒子の分散液の形態のいずれかで、ナノ粒子に含まれる光吸収剤を調製する工程;
c)前記モノマー又はオリゴマーの重合を開始するための触媒を準備する工程;
d)紫外線吸収剤を準備する工程;
e)ナノ粒子が分散されている重合性液体組成物を得るために、モノマー又はオリゴマーと、ナノ粒子と、触媒と、紫外線吸収剤とを混合する工程;
e)任意選択的に重合性液体組成物を基材上に堆積させる工程;
f)重合性液体組成物を硬化させる工程;
を含む。
本発明は、モノマー又はオリゴマーの重合を開始するための触媒による前記光吸収剤の分解を防止するためにナノ粒子中に含まれている光吸収剤の使用にも関する。触媒による光吸収剤の分解の防止は、重合前の組成物の吸収スペクトルを重合後の眼鏡用レンズのものと比較することによって評価することができる。眼鏡用レンズの吸収スペクトルが光吸収剤の最大吸収波長で同じ透過率の低下を示す場合、光吸収剤は重合中に触媒によって分解されないとみなすことができる。
以降の測定は、イソプロピルアルコールで洗浄された、中心の厚さが2mmのレンズに対して行う。
実施例では次の化合物を使用する:
様々な紫外線吸収剤を使用した。紫外線吸収剤の吸光度は、厚さ2mmの石英キュベット中、400nmの波長で、0.4mM/Lの紫外線吸収剤を含有するエタノール溶液中で測定した。ブランクとしての純粋なエタノールを参照として測定する(表1)。
実施例2a:シクロヘキサン(7.5ml)、n-ヘキサノール(1.8ml)、Triton X-100(1.5g)、OMNISTAB(商標)47(40mg、Deltachem Co;Ltdから入手可能)、TEOS(0.1ml)、及び水酸化アンモニウム30%(0.06ml)の混合物を24時間混合する。その後、アセトンを添加し、粒子を遠心分離によって回収し、エタノールで洗浄して乾燥させる。ナノ粒子は、100nmを中心とする単分散のサイズ、及び約1.47の沈降シリカに対応する屈折率を有する。
実施例3a:実施例2cで得たナノ粒子を36.5重量%のテトラブチルオルトチタネート(TBOT)の水溶液の中に入れる。
384mLのメタノールを1000mlの瓶に入れる。次いで、96mlのNH4OH(30重量%水溶液)及び6.4mlのメチレンブルー(CAS:61-73-4、2重量%の脱イオン水溶液)を添加する。混合物を400rpmで10分間撹拌する(磁気撹拌)。その後、3.2mlのTEOSを滴下し、800rpmで2時間撹拌する。
実施例4で得たナノ粒子を36.5重量%のテトラブチルオルトチタネート(TBOT)の水溶液の中に入れる。
Claims (11)
- a)モノマー又はオリゴマーの重合を開始するための触媒の存在下で、少なくとも1種のアリル又は非アリル系のモノマー又はオリゴマーを重合することによって得られるマトリックス、
b)前記マトリックス中に分散されているナノ粒子の中に含まれる少なくとも1種の光吸収剤、
c)少なくとも1種の紫外線吸収剤、
を含む複合基材を含む眼鏡用レンズであって:
厚さ2mmの眼鏡用レンズの光透過率が280~400nmの範囲の各光波長で1%未満であり、430nmの波長を有する光では65%超である、眼鏡用レンズ。 - 前記マトリックスが、ポリアミド、ポリイミド、ポリスルホン、ポリカーボネート、ポリエチレンテレフタレート、ポリ(メチル(メタ)アクリレート)、セルローストリアセテート、又はこれらのコポリマーなどの熱可塑性樹脂から選択される、あるいは環状オレフィンコポリマー、アリルエステルのホモポリマー又はコポリマー、直鎖又は分岐の脂肪族又は芳香族ポリオールの炭酸アリルのホモポリマー又はコポリマー、(メタ)アクリル酸及びそのエステルのホモポリマー又はコポリマー、チオ(メタ)アクリル酸及びそのエステルのホモポリマー又はコポリマー、ウレタン及びチオウレタンのホモポリマー又はコポリマー、エポキシのホモポリマー又はコポリマー、スルフィドのホモポリマー又はコポリマー、ジスルフィドのホモポリマー又はコポリマー、エピスルフィドのホモポリマー又はコポリマー、チオール及びイソシアネートのホモポリマー又はコポリマーなどの熱硬化性樹脂、並びにこれらの組み合わせから選択される、請求項1に記載の眼鏡用レンズ。
- 前記光吸収剤が、染料若しくは顔料などの着色剤、無色の光吸収剤、又はこれらの混合物から選択され、好ましくは着色剤である、請求項1又は2に記載の眼鏡用レンズ。
- 前記ナノ粒子がポリマーを含み、好ましくは前記ナノ粒子が、アクリルポリマー、ビニルポリマー、アリルポリマー、及びこれらの混合物からなる群から選択されるポリマーを含む、請求項1~3のいずれか1項に記載の眼鏡用レンズ。
- ナノ粒子が無機酸化物を含み、好ましくは、前記ナノ粒子がSiO2、TiO2、ZrO2、Al2O3、及びこれらの混合物からなる群の中で選択される無機酸化物を含む、請求項1~3のいずれか1項に記載の眼鏡用レンズ。
- 動的光散乱法に従って測定される前記ナノ粒子のサイズが1nm~10μm、好ましくは10nm~5μmである、請求項1~5のいずれか1項に記載の眼鏡用レンズ。
- 前記ナノ粒子中の前記光吸収剤の量が、前記ナノ粒子の重量を基準として0.0001~90重量%、特には0.01~50重量%、より具体的には0.1~10重量%である、請求項1~6のいずれか1項に記載の眼鏡用レンズ。
- 前記組成物中のナノ粒子の量が、前記組成物の総重量を基準として0.001重量%~1重量%、好ましくは0.0025重量%~0.1重量%である、請求項1~7のいずれか1項に記載の眼鏡用レンズ。
- 紫外線吸収剤が、
a)ベンゾフェノン誘導体、特には2,2’-ジヒドロキシ-4,4’-ジメトキシベンゾフェノン、2,2’-ジヒドロキシ-4-メトキシベンゾフェノン、及び2,2’,4,4’-テトラヒドロキシベンゾフェノン;又は
b)ベンゾトリアゾール誘導体、特には2-(2-ヒドロキシ-3-tert-ブチル-5-メチルフェニル)-5-クロロ-2H-ベンゾトリアゾール及び2-(2H-ベンゾトリアゾール-2-イル)-6-(1-メチル-1-フェニルエチル)-4-(1,1,3,3-テトラメチルブチル)フェノール;又は
c)少なくとも1つのエステル基を有するクロロベンゾトリアゾール化合物、特には式(IV)の化合物:
(式中、Aは二価の基であり、R1はクロロ基であり、R2基は同じ又は異なる一価の基であり、nは1~3の範囲の整数であり、R3は直鎖又は分岐の置換又は無置換のアルキル又はアリール基である)であって、アリル、アクリル、及びメタクリル部位から選択される重合性基を含まないクロロベンゾトリアゾール化合物;又は
d)2-(2-ヒドロキシ-5-R1-フェニル)ベンゾトリアゾール(式中、R1は、アミノ、ヒドロキシル、アルコキシ、アリールオキシ、アルキルアミノ、アリールアミノ、ジアルキルアミノ、ジアリールアミノ、(アリール)(アルキル)アミノ、ホルムアミド、アルキルアミド、アリールアミド、ホルミルオキシ、アルキルカルボキシ、アリールカルボキシ、アルキルイミノ、及びアリールイミノの基から選択される共鳴基である)、特には式(I)の化合物
(式中、R1は共鳴基であり、R2基は、同じ又は異なる一価の基であり、nは0又は1の整数であり、R3基は同じ又は異なる一価の基であり、mは0~2の範囲の整数である);又は
e)トリアジン誘導体;又は
f)オキサラニリド誘導体;又は
g)これらの混合物;
から選択される、請求項1~8のいずれか1項に記載の眼鏡用レンズ。 - a)前記マトリックスを調製することができるモノマー又はオリゴマーを準備する工程;
b)前記モノマー又はオリゴマーの中に分散可能な粉末の形態か、前記モノマー又はオリゴマーの中に分散可能な液体中のナノ粒子の分散液の形態で、ナノ粒子の中に含まれる光吸収剤を調製する工程;
c)前記モノマー又はオリゴマーの前記重合を開始するための触媒を準備する工程;
d)紫外線吸収剤を準備する工程;
e)ナノ粒子が分散されている重合性液体組成物を得るために、前記モノマー又はオリゴマーと、前記ナノ粒子と、前記触媒と、前記紫外線吸収剤とを混合する工程;
e)任意選択的に前記重合性液体組成物を基材上に堆積させる工程;
f)前記重合性液体組成物を硬化させる工程;
を含む、請求項1~9のいずれか1項に記載の眼鏡用レンズの作製方法。 - モノマー又はオリゴマーの重合を開始するための触媒による前記光吸収剤の分解を防止するための、特に前記眼鏡用レンズの黄変を防止するための、請求項1~10のいずれか1項に記載の眼鏡用レンズ内に分散されているナノ粒子中に含まれる光吸収剤の使用。
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PCT/EP2018/081403 WO2019110264A1 (en) | 2017-12-08 | 2018-11-15 | Composition for the manufacture of an ophtalmic lens comprising an encapsulated light-absorbing additive |
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