JP7407945B2 - セグメント化ポリマーを含有する硬化性フォトクロミック組成物 - Google Patents
セグメント化ポリマーを含有する硬化性フォトクロミック組成物 Download PDFInfo
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- JP7407945B2 JP7407945B2 JP2022539171A JP2022539171A JP7407945B2 JP 7407945 B2 JP7407945 B2 JP 7407945B2 JP 2022539171 A JP2022539171 A JP 2022539171A JP 2022539171 A JP2022539171 A JP 2022539171A JP 7407945 B2 JP7407945 B2 JP 7407945B2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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- C09D5/29—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for multicolour effects
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
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- C08G18/22—Catalysts containing metal compounds
- C08G18/227—Catalysts containing metal compounds of antimony, bismuth or arsenic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6275—Polymers of halogen containing compounds having carbon-to-carbon double bonds; halogenated polymers of compounds having carbon-to-carbon double bonds
- C08G18/6279—Polymers of halogen containing compounds having carbon-to-carbon double bonds; halogenated polymers of compounds having carbon-to-carbon double bonds containing fluorine atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1545—Six-membered rings
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
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Description
(a)フォトクロミック化合物と、
(b)活性水素基と、少なくとも1つの第1セグメントと、少なくとも1つの第2セグメントとを含むセグメント化ポリマーであって、
(i)各々の第1セグメントが独立に、フッ素化ポリマーセグメントを含み、及び
(ii)各々の第2セグメントが独立に、ポリカーボネートセグメント、ポリエステルセグメント、ポリエーテルセグメント、ポリウレタンセグメント、及びそれらのコポリマーのセグメントからなる群から選択されるセグメントを含む、セグメント化ポリマーと、
(c)セグメント化ポリマーの活性水素基と反応性である反応性官能基を含む硬化剤であって、ポリイソシアネート、ポリイソチオシアネート、又はアミノプラストのうちの少なくとも1つを含む、硬化剤とを含む、硬化性フォトクロミック組成物を目的としている。
(a)フォトクロミック化合物と、
(b)活性水素基と、少なくとも1つの第1セグメントと、少なくとも1つの第2セグメントとを含むセグメント化ポリマーであって、
(i)各々の第1セグメントが独立に、フッ素化ポリマーセグメントを含み、及び
(ii)各々の第2セグメントが独立に、ポリカーボネートセグメント、ポリエステルセグメント、ポリエーテルセグメント、ポリウレタンセグメント、及びそれらのコポリマーのセグメントからなる群から選択されるセグメントを含む、セグメント化ポリマーと、
(c)セグメント化ポリマーの活性水素基と反応性である反応性官能基を含む硬化剤であって、ポリイソシアネート、ポリイソチオシアネート、又はアミノプラストのうちの少なくとも1つを含む硬化剤とを含む、硬化性フォトクロミック組成物。
セグメント化ポリマー(b)が、1,000~15,000g/eqの活性水素当量を有し、及び
セグメント化ポリマー(b)の各々の活性水素基が独立にヒドロキシル基、チオール基、第一アミン基、及び第二アミン基からなる群から選択される、条項1又は2に記載の硬化性フォトクロミック組成物。
硬化剤(c)が、反応性イソシアネート基を含むポリイソシアネート、及び/又は反応性イソチオシアネート基を含むポリイソチオシアネートのうちの少なくとも1つを含み、及び
硬化剤(c)の反応性官能基の、セグメント化ポリマー(b)の活性水素基に対するモル比が少なくとも4:1である、条項1~8のいずれか1つに記載のフォトクロミック組成物。
(A)基材と、
(B)基材の少なくとも1つの表面の上のフォトクロミック層であって、条項1~15のいずれか1つに記載の硬化性フォトクロミック組成物から形成される、フォトクロミック層とを含む、物品。
ポリカーボネート-ポリエステルジオールセグメントの調製において使用される材料を表1に要約する。ポリカーボネート-ポリエステルジオールセグメントをそれぞれ、機械的攪拌機及びDean Starkトラップを備えた丸底フラスコ内で合成した。投入物1を導入した後、各々の反応混合物を窒素ブランケット下で170℃まで加熱し、強い還流を生じた。キシレンと水をDean Starkトラップから必要に応じて除去して、温度を180℃未満に7時間まで維持し、その時に酸価を測定すると<1mgKOH/gであった。この時点で、反応混合物を130℃に冷却し、次に投入物2の添加によって表1に示される固形分レベルに低減した。
セグメント化ポリマーの調製(比較例1)~(実施例8)は、表2を参照して以下のように説明される。
表2に従って投入物A、B及びCをアニソール(121g)と一緒に組み合わせて、2.5時間の間80℃に加熱した。サンプルを75℃に冷却し、アニソール(16g)中の投入物Eを添加した。10分後に投入物Fをアニソール(5g)と一緒に添加した。75℃で30分後に温度を3.5時間の間80℃に上昇させた。Surface SWYPETMパッドを使用する試験(CLI Laboratories Inc.から入手可能、パッド上に置かれる時に反応溶液の液滴は、遊離イソシアネートが存在している時に橙色又は赤色への色の変化を生じた)はイソシアネートがまだ存在していることを示した。1-プロパノール(2mL)を添加して反応を急冷し、1.5時間後に、Surface SWYPETMパッドを使用する試験はイソシアネートが存在していないことを示し、溶液を冷却して粘性液体をもたらした。
表2に従って投入物A、B及びCをアニソール(116g)と一緒に組み合わせて、2.5時間の間80℃に加熱した。サンプルを70℃に冷却し、アニソール(13g)中の投入物Eを添加した。10分後にアニソール(28g)に溶解された投入物Fを付加的なアニソール(8g)と共に添加した。70℃で30分後に温度を2.5時間の間80℃に上昇させた。Surface SWYPETMパッドを使用する試験はイソシアネートが存在していないことを示し、溶液を冷却して粘性液体をもたらした。
表2に従って投入物A、B及びCをAromatic 150(87g)と一緒に組み合わせて、2.5時間の間80℃に加熱した。サンプルを75℃に冷却し、Aromatic 150(27g)に溶解された投入物Dを添加した。10分後にAromatic 150(34g)に溶解された投入物Fを付加的なAromatic 150(8g)と一緒に添加した。30分後に温度を2時間の間80℃に上昇させた。Surface SWYPETMパッドを使用する試験はイソシアネートが存在していないことを示し、溶液を冷却して粘性液体をもたらした。
表2に従って投入物A、B及びCをm-キシレン(129g)と一緒に組み合わせて、2.5時間の間80℃に加熱した。サンプルを70℃に冷却し、m-キシレン(14g)中の投入物Eを添加した。10分後に投入物Fを添加した。70℃で60分後に温度を1時間の間85℃に上昇させた。Surface SWYPETMパッドを使用する試験はイソシアネートが存在していないことを示し、溶液を冷却して粘性液体をもたらした。
表2に従って投入物A、B及びCをAromatic 150(90g)と一緒に組み合わせて、2.5時間の間80℃に加熱した。サンプルを75℃に冷却し、Aromatic 150(11g)に溶解された投入物Dを付加的なAromatic 150(4g)と一緒に添加した。30分後にAromatic 150(7g)中の投入物Eを添加した。10分後に投入物Fを付加的なAromatic 150(11g)と一緒に添加した。30分後に温度を2時間の間80℃に上昇させた。Surface SWYPETMパッドを使用する試験はイソシアネートが存在していないことを示し、溶液を冷却して粘性液体をもたらした。
表2に従って投入物A、B及びCをAromatic 150(110g)と一緒に組み合わせて、2.5時間の間80℃に加熱した。サンプルを75℃に冷却し、Aromatic 150(10g)に溶解された投入物Dを付加的なAromatic 150(4g)と一緒に添加した。30分後にAromatic 150(24g)に溶解された投入物Fを付加的なAromatic 150(10g)と一緒に添加した。2.5時間後に、Surface SWYPETMパッドを使用する試験はイソシアネートがまだ存在していることを示した。1-プロパノール(2mL)を添加して反応を急冷し、30分後に、Surface SWYPETMパッドを使用する試験はイソシアネートが存在していないことを示し、溶液を冷却して粘性液体をもたらした。
表2に従って投入物A、B及びCをAromatic 150(41g)と一緒に組み合わせて、2.5時間の間80℃に加熱した。サンプルを75℃に冷却し、Aromatic 150(16g)に溶解された投入物Dを添加した。30分後にAromatic 150(9g)に溶解された投入物Fを添加した。30分後に温度を2時間の間80℃に上昇させた。Surface SWYPETMパッドを使用する試験はイソシアネートが存在していないことを示し、溶液を冷却して粘性液体をもたらした。
表2に従って投入物A、B及びCをAromatic 150(251g)と一緒に組み合わせて、及び3時間の間80℃に加熱した。サンプルを70℃に冷却し、Aromatic 150(6g)と混合された投入物Eを添加した。30分後に投入物Fを添加した。2時間後にSurface SWYPETMパッドを使用する試験はイソシアネートが存在していないことを示し、溶液を冷却して粘性液体をもたらした。
全ての固形分が溶解したのが観察されるまで表3に記載された材料を周囲環境で混合することによってフォトクロミック溶液(A)及び(B)を調製した。
比較用硬化性フォトクロミック組成物:
比較用硬化性フォトクロミック組成物(比較例9、比較例10)を表4に記載された成分から調製した。比較例9は、単一成分として添加されるフッ素化ポリオールセグメント及びポリカーボネートジオールセグメントを使用する代表的な硬化性フォトクロミック組成物である。比較例10は、(メタ)アクリルポリオールセグメント及びポリカーボネート-ポリエステルジオールセグメントから構成されるセグメント化ポリマーを使用する硬化性フォトクロミック組成物を代表する。
本発明の硬化性フォトクロミック組成物の実施例11~17を表5に記載された成分から調製した。比較例について上述した手順に従って実施例を調製した。
パートCにおいて上で調製した硬化性フォトクロミック組成物の実施例の各々を、76ミリメートルの直径を有するPDQ(登録商標)コーテッドGENTEX(登録商標)ポリカーボネートプラノレンズ(Gentex Optics,Inc.から入手可能)に塗布した。全てのレンズ基材を3分間100Wの電力で酸素の100ミリリットル(mL)/分の流量で酸素プラズマにより処理し、次に、スピンコーティングによってパートCにおいて説明された硬化性フォトクロミック組成物の実施例の各々でコートした。約1~2mLの各々の硬化性フォトクロミック組成物をレンズ基材上に供給し、次に、湿潤コーティングをレンズ上に堆積するために十分なスピン速度でそれを8~13秒間回転させ、パートEにおいて以下に説明されるように、同様な活性化された光学濃度を生じる。スピンコーティングパラメーターは表6に報告される。
レンズセットAの試験片は、15秒間100ニュートンの負荷後に2ミクロンの透過度でFischerscope HCV、Model H100SMC装置(Fischer Technology,Inc.から入手可能)を使用して微小硬さ試験に供された。各々の試験片を2~5回測定し、微小硬さの結果を平均して、表15に記載する。
Claims (18)
- (a)フォトクロミック化合物と、
(b)活性水素基と、少なくとも1つの第1セグメントと、少なくとも1つの第2セグメントとを含むセグメント化ポリマーであって、
(i)各々の第1セグメントが独立に、フッ素化ポリマーセグメントを含み、及び
(ii)各々の第2セグメントが独立に、ポリカーボネートセグメント、ポリエステルセグメント、ポリエーテルセグメント、ポリウレタンセグメント、及びそれらのコポリマーのセグメントからなる群から選択されるセグメントを含む、
セグメント化ポリマーと、
(c)前記セグメント化ポリマーの前記活性水素基と反応性である反応性官能基を含む硬化剤であって、ポリイソシアネート、ポリイソチオシアネート、又はアミノプラストのうちの少なくとも1つを含む、硬化剤
とを含む、硬化性フォトクロミック組成物。 - 各々の第2セグメント(ii)の少なくとも一部が、活性水素含有化合物に由来する基を終端とする、請求項1に記載の硬化性フォトクロミック組成物。
- 前記セグメント化ポリマー(b)が、1,000~15,000g/eqの活性水素当量を有し、及び
前記セグメント化ポリマー(b)の各々の活性水素基が独立に、ヒドロキシル基、チオール基、第一アミン基、及び第二アミン基からなる群から選択される、
請求項1又は2に記載の硬化性フォトクロミック組成物。 - 前記セグメント化ポリマー(b)の各々の活性水素基がヒドロキシルである、請求項1~3のいずれか一項に記載の硬化性フォトクロミック組成物。
- 少なくとも1つの第1セグメント(i)及び少なくとも1つの第2セグメント(ii)が、カルボン酸エステル連結基、チオエステル連結基、アミド連結基、ウレタン連結基、チオウレタン連結基、尿素連結基、チオ尿素連結基、カーボネート連結基、エーテル連結基、及びチオエーテル連結基からなる群から選択される連結基によって互いに共有結合によって結合している、請求項1~4のいずれか一項に記載の硬化性フォトクロミック組成物。
- 前記第2セグメント(ii)が、前記セグメント化ポリマーの総重量を基準として前記セグメント化ポリマー(b)中に40重量パーセント~95重量パーセントの量で存在している、請求項1~5のいずれか一項に記載の硬化性フォトクロミック組成物。
- 前記硬化性フォトクロミック組成物の全固形分重量を基準として15重量パーセント~50重量パーセントの第2セグメント(ii)の総量を含む、請求項1~6のいずれか一項に記載の硬化性フォトクロミック組成物。
- 各々の第2セグメント(ii)が独立に、ポリカーボネートセグメント、ポリカーボネート-ポリエステルセグメント、ポリカーボネート-ポリウレタンセグメント、ポリエーテルセグメント、又はポリカーボネート-ポリエステル-ポリウレタンセグメントの少なくとも1つを含む、請求項1~7のいずれか一項に記載の硬化性フォトクロミック組成物。
- 前記硬化剤(c)が、反応性イソシアネート基を含むポリイソシアネート、又は反応性イソチオシアネート基を含むポリイソチオシアネートの少なくとも1つを含み、
及び
前記硬化剤(c)の反応性官能基の、前記セグメント化ポリマー(b)の活性水素基に対するモル比が少なくとも4:1である、
請求項1~8のいずれか一項に記載の硬化性フォトクロミック組成物。 - 前記硬化剤(c)の反応性官能基の、前記セグメント化ポリマー(b)の活性水素基に対するモル比が少なくとも5:1且つ60:1以下である、請求項1~9のいずれか一項に記載の硬化性フォトクロミック組成物。
- 前記硬化剤(c)が、反応性イソシアネート基を含むポリイソシアネートを含む、請求項1~10のいずれか一項に記載の硬化性フォトクロミック組成物。
- 前記ポリイソシアネートが脂肪族ポリイソシアネートである、請求項11に記載の硬化性フォトクロミック組成物。
- 前記硬化剤(c)がポリイソシアネートを含み、ポリイソシアネート硬化剤を構成する前記反応性イソシアネート基の少なくとも一部がブロッキング剤でブロックされ、各々のブロッキング剤が独立に、メチルエチルケトキシム、ピラゾール、及びジアルキルピラゾールからなる群から選択される、請求項1~12のいずれか一項に記載の硬化性フォトクロミック組成物。
- 前記フォトクロミック化合物(a)が、ナフトピラン、ベンゾピラン、フェナントロピラン、インデノナフトピラン、スピロ(インドリン)ナフトキサジン、スピロ(インドリン)ピリドベンゾキサジン、スピロ(ベンズインドリン)ピリドベンゾキサジン、スピロ(ベンズインドリン)ナフトキサジン、スピロ(インドリン)-ベンゾオキサジン、フルギド、フルギミド、及びこのようなフォトクロミック化合物の混合物からなる群から選択される、請求項1~13のいずれか一項に記載の硬化性フォトクロミック組成物。
- 前記フッ素化ポリマーセグメントが活性水素基を含む、請求項1~14のいずれか一項に記載の硬化性フォトクロミック組成物。
- 請求項1~15のいずれか一項に記載の硬化性フォトクロミック組成物を含むポリマーフィルム。
- (A)基材と、
(B)前記基材の少なくとも1つの表面の上のフォトクロミック層であって、請求項1~15のいずれか一項に記載の硬化性フォトクロミック組成物から形成される、フォトクロミック層
とを含む物品。 - 請求項1~15のいずれか一項に記載の硬化性フォトクロミック組成物から形成される、少なくとも1つのフォトクロミック層を含むフォトクロミック複数層物品。
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ES2971851T3 (es) | 2024-06-10 |
EP4081610B1 (en) | 2023-12-06 |
MX2022008032A (es) | 2022-08-17 |
AU2019479670A1 (en) | 2022-07-28 |
US20230048395A1 (en) | 2023-02-16 |
BR112022012763A2 (pt) | 2022-11-16 |
EP4081610A1 (en) | 2022-11-02 |
CA3165934A1 (en) | 2021-07-01 |
CN114929834A (zh) | 2022-08-19 |
JP2023515746A (ja) | 2023-04-14 |
WO2021129941A1 (en) | 2021-07-01 |
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