JP5014981B2 - 着色シリコーンヒドロゲルレンズ製造用硬化性着色インク - Google Patents
着色シリコーンヒドロゲルレンズ製造用硬化性着色インク Download PDFInfo
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- JP5014981B2 JP5014981B2 JP2007508839A JP2007508839A JP5014981B2 JP 5014981 B2 JP5014981 B2 JP 5014981B2 JP 2007508839 A JP2007508839 A JP 2007508839A JP 2007508839 A JP2007508839 A JP 2007508839A JP 5014981 B2 JP5014981 B2 JP 5014981B2
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- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- DCBBWYIVFRLKCD-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-methylprop-2-enamide Chemical compound CN(C)CCNC(=O)C(C)=C DCBBWYIVFRLKCD-UHFFFAOYSA-N 0.000 description 1
- JTHNLKXLWOXOQK-UHFFFAOYSA-N n-propyl vinyl ketone Natural products CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 238000010944 pre-mature reactiony Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- TVRGPOFMYCMNRB-UHFFFAOYSA-N quinizarine green ss Chemical compound C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1 TVRGPOFMYCMNRB-UHFFFAOYSA-N 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- 238000011282 treatment Methods 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00038—Production of contact lenses
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00865—Applying coatings; tinting; colouring
- B29D11/00894—Applying coatings; tinting; colouring colouring or tinting
- B29D11/00903—Applying coatings; tinting; colouring colouring or tinting on the surface
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00865—Applying coatings; tinting; colouring
- B29D11/00923—Applying coatings; tinting; colouring on lens surfaces for colouring or tinting
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/056—Forming hydrophilic coatings
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/04—Contact lenses for the eyes
- G02C7/046—Contact lenses having an iris pattern
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2483/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
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- General Health & Medical Sciences (AREA)
- Eyeglasses (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
- Polyurethanes Or Polyureas (AREA)
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Description
本実施例は、光硬化性バインダーポリマー前駆体の合成および光硬化性バインダーポリマーの合成について記載する。
ペンダント官能基を有するシリコーン含有ポリマーの合成
光硬化性バインダーポリマーの調製
本実施例は、本発明のバインダーポリマーが、シリコーンヒドロゲルレンズ製造用レンズ形成材料においてプレポリマーとして使用できることを例示する。
シリコーンヒドロゲルコンタクトレンズ製造用レンズ形成材料(LF−4)は、バインダーポリマーC2の61%エタノール溶液(インク6の調製で記載されている通り、バインダーポリマーC2中の酢酸エチルをエタノールと交換する)18.04gを2.03gのエタノール中の0.0192gのIrgacure2959からなる溶液と混合することによって調製する。混合しかつ遠心分離した後に、得られたポリマー溶液の粘度は、25.0℃で約1310cpsである。ポリプロピレンレンズ(FreshLook)モールドに試料を充填する。次いで、充填したモールドを2.02mW/cm2で約10秒間照射する。ヒドロゲルレンズをモールドから回収し、BBSに入れ、滅菌する。レンズの含水率は約21%である。
シリコーン含有マクロマーの合成
平均分子量が1030g/molであり、末端基滴定によるヒドロキシル基1.96meq/gを含むペルフルオロポリエーテルFomblin(登録商標)ZDOL(Ausimont S.p.A、Milan製)51.5g(50mmol)を、50mgのジブチルスズジラウラートと共に三つ口フラスコに導入する。フラスコ内容物を約20mbarになるまで攪拌しながら排気し、続いてアルゴンで減圧する。この操作を2度繰り返す。続いて、アルゴン下で保管されている新たに蒸留したイソホロンジイソシアナート22.2g(0.1mol)をアルゴン向流中に加える。水浴で冷却することによって、フラスコ内温度を30℃未満に維持する。終夜室温で攪拌した後に、反応は終了する。イソシアナート滴定によって、NCO含有量が1.40meq/g(理論上:1.35meq/g)ことが分かる。Shin-Etsu社製であり、平均分子量が2000g/mol(滴定によるヒドロキシル基1.00meq/g)のα,ω−ヒドロキシプロピル末端ポリジメチルシロキサンKF−6001 202gをフラスコに導入する。フラスコ内容物を約0.1mbarになるまで排気し、アルゴンで減圧する。この操作を2度繰り返す。脱気したシロキサンをアルゴン下で保管されている新たに蒸留したトルエン202mlに溶解し、100mgのジブチルスズジラウラート(DBTDL)を加える。溶液を完全に均質化した後に、イソホロンジイソシアナート(IPDI)と反応したペルフルオロポリエーテルの全てをアルゴン下で加える。終夜室温で攪拌した後に、反応が終了する。溶媒を高真空下室温でストリップして除去する。ミクロ滴定は、ヒドロキシル基0.36meq/g(理論上0.37meq/g)を示す。
本実施例は、インクおよび着色シリコーンヒドロゲルコンタクトレンズの調製を例示する。
インクの調製
レンズ形成材料
シリコーンヒドロゲルレンズ上にプリントされたインクの付着試験
Claims (10)
- 着色シリコーンヒドロゲルコンタクトレンズを製造するためのインクであって、少なくとも一種の着色剤、溶媒、およびエチレン性不飽和基と、少なくとも一種のシリコーン含有ビニルモノマーもしくはビニルマクロマーに由来するセグメントとを含むシリコーン含有バインダーポリマーを含み、
前記シリコーン含有バインダーポリマーが、
(1)重合可能組成物を共重合させてシリコーン含有ポリマーを得て(該重合可能組成物は、(a)少なくとも一種の官能基を有しない親水性ビニルモノマー;
(b)ヒドロキシル基、一級アミノ基、二級アミノ基、カルボキシル基、エポキシ基、アルデヒド基、アミド基、酸ハライド基、イソチオシアナート基、イソシアナート基、ハライド基、酸無水物基、およびそれらの組合せからなる群から選択される少なくとも1個の第一の官能基を含む少なくとも一種の官能化用ビニルモノマー;
(c)少なくとも一種のシリコーン含有ビニルモノマーもしくはビニルマクロマー、を含み、
前記シリコーン含有ポリマーは、官能化用ビニルモノマー由来の第一の官能基を有する)、
(2)前記シリコーン含有ポリマーを、エチレン性不飽和基および第二の官能基を含むエチレン性官能化用剤と反応させる(ここで、前記シリコーン含有ポリマーの第一の官能基と前記エチレン性官能化用剤の第二の官能基とが反応して共有結合が形成される)ことによって得られる、
インク。 - 前記インクが、化学線または熱硬化されてコンタクトレンズ上に着色塗膜を形成する能力を有し、硬化後にモールドからコンタクトレンズへの良好な転移性を有する、請求項1のインク。
- 溶媒量が10%〜95重量%であり、バインダーポリマー量が1%〜90重量%であり、かつ着色剤量が0.05%〜25重量%である、請求項1または2のインク。
- 前記着色剤が、溶媒にやや溶けにくいかまたは溶媒に不溶性のいずれかである、少なくとも一種の顔料および/または少なくとも一種の染料を含む、請求項1〜3のいずれかのインク。
- 前記シリコーン含有ビニルモノマーが、3−メタクリロキシプロピルペンタメチルジシロキサン、ビス(メタクリロキシプロピル)テトラメチル−ジシロキサン、モノメタクリル化したポリジメチルシロキサン、メルカプト末端ポリジメチルシロキサン、N−[トリス(トリメチルシロキシ)シリルプロピル]アクリルアミド、トリストリメチルシリルオキシシリルプロピルメタクリラート(TRIS)、またはN−[トリス(トリメチルシロキシ)シリルプロピル]−メタクリルアミドである、請求項1〜4のいずれかのインク。
- 前記官能化用ビニルモノマーが、メタクリル酸(MAA)、アクリル酸、グリシジルメタクリラート、グリシジルアクリラート、2−ヒドロキシエチルメタクリラート(HEMA)、2−ヒドロキシエチルアクリラート(HEA)、メタクリル酸無水物、N−ヒドロキシメチルアクリルアミド(NHMA)、または2−ブロモエチルメタクリラートである、請求項1〜5のいずれかのインク。
- 前記重合可能組成物が、メルカプトエタン、メルカプトエタノール、エタンジチオール、プロパンジチオール、およびメルカプト末端ポリジメチルシロキサンからなる群から選択される連鎖移動剤を含む、請求項1〜6のいずれかのインク。
- 前記エチレン性官能化用剤が、グリシジルメタクリラート、グリシジルアクリラート、2−イソシアナトエチルメタクリラート(IEM)、N−ヒドロキシメチルアクリルアミド(NHMA)、アクリロイルクロリド、メタクリロイルクロリド、メタクリル酸、アクリル酸、2−ブロモエチルメタクリラート、またはメタクリル酸無水物である、請求項1〜7のいずれかのインク。
- 着色シリコーンヒドロゲルコンタクトレンズを製造する方法であって、
(a)シリコーンヒドロゲルで構築したコンタクトレンズを供するステップ、
(b)請求項1〜8のいずれかのインクでレンズ表面の少なくとも一部に着色被膜を適用するステップ、並びに
(c)該インクを硬化させ、それによって色塗をレンズに付着させるステップ
を含む方法。 - 着色シリコーンヒドロゲルコンタクトレンズを製造する方法であって、
(a)請求項1〜8のいずれかのインクでレンズモールドの成形面の少なくとも一面の少なくとも一部に着色塗膜を適用するステップ、
(b)色塗を定位置に実質的に維持しながら、該モールドのレンズ形成用キャビティにレンズ形成材料を分注するステップ、および
(c)レンズ形成用キャビティ内でレンズ形成材料を硬化させてコンタクトレンズを形成し、それによって着色塗膜が成形面から脱離し、着色コンタクトレンズ本体と一体になるステップ
を含む方法。
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US56402404P | 2004-04-21 | 2004-04-21 | |
US60/564024 | 2004-04-21 | ||
PCT/EP2005/004247 WO2005102675A2 (en) | 2004-04-21 | 2005-04-20 | Curable colored inks for making colored silicone hydrogel lenses |
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JP2007538113A JP2007538113A (ja) | 2007-12-27 |
JP5014981B2 true JP5014981B2 (ja) | 2012-08-29 |
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ZA (1) | ZA200608022B (ja) |
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2005
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CN1947033B (zh) | 2013-07-10 |
US20090252868A1 (en) | 2009-10-08 |
NO342082B1 (no) | 2018-03-19 |
AU2005234905B2 (en) | 2008-07-31 |
PT1756625E (pt) | 2014-09-03 |
PL1756625T3 (pl) | 2014-11-28 |
US20140039086A1 (en) | 2014-02-06 |
ES2498971T3 (es) | 2014-09-26 |
BRPI0510086A (pt) | 2007-10-16 |
WO2005102675A3 (en) | 2006-03-30 |
CN1947033A (zh) | 2007-04-11 |
US7550519B2 (en) | 2009-06-23 |
EP1756625B1 (en) | 2014-06-04 |
CA2561788C (en) | 2013-05-21 |
AU2005234905A1 (en) | 2005-11-03 |
MXPA06012125A (es) | 2007-01-17 |
US20050237483A1 (en) | 2005-10-27 |
ZA200608022B (en) | 2008-07-30 |
DK1756625T3 (da) | 2014-08-11 |
BRPI0510086B1 (pt) | 2019-04-24 |
CA2561788A1 (en) | 2005-11-03 |
US8622543B2 (en) | 2014-01-07 |
JP2007538113A (ja) | 2007-12-27 |
EP1756625A2 (en) | 2007-02-28 |
WO2005102675A2 (en) | 2005-11-03 |
NO20065310L (no) | 2007-01-22 |
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