JP7466629B2 - ポリオールとポリ(無水物)とを含むフォトクロミック組成物 - Google Patents
ポリオールとポリ(無水物)とを含むフォトクロミック組成物 Download PDFInfo
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- JP7466629B2 JP7466629B2 JP2022513280A JP2022513280A JP7466629B2 JP 7466629 B2 JP7466629 B2 JP 7466629B2 JP 2022513280 A JP2022513280 A JP 2022513280A JP 2022513280 A JP2022513280 A JP 2022513280A JP 7466629 B2 JP7466629 B2 JP 7466629B2
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- polyol
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005213 imbibition Methods 0.000 description 1
- UEOGLANRPZAEAC-UHFFFAOYSA-N indeno-naphthopyran Chemical compound O1C=CC=C2C3=C4C=C(C=CC=C5)C5=C4C=CC3=CC=C21 UEOGLANRPZAEAC-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
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- 238000005580 one pot reaction Methods 0.000 description 1
- 238000000424 optical density measurement Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
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- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
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- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- 150000003573 thiols 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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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
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
-
- 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
- C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
- C08G18/4615—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen
-
- 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
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5036—Polyethers having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
- C08G18/5045—Polyethers having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing urethane groups
-
- 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
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- 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
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/80—Processes for incorporating ingredients
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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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/23—Photochromic filters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Optical Filters (AREA)
- Eyeglasses (AREA)
- Paints Or Removers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
実施例1
ポリカプロラクトンテトラオール
ペンタエリスリトール(6g)及びε-カプロラクトン(126g)を窒素下で3口フラスコ中で合わせ、均一になるまで150℃に加熱した。オクタン酸スズ(II)(1g)を5分間かけて添加したところ、180℃まで発熱した。フラスコを脱気し、窒素で3回パージし、その後窒素下で150℃で24時間撹拌した。冷却した反応混合物にヘキサン(3×300mL)を添加し、各添加後に上澄みをデカンテーションした。得られた粘稠な液体を真空下で40℃で乾燥させることで、低融点の白色固体(収量:107g)を得た。1H NMRによって3332g/molの分子量及び833g/molのヒドロキシル当量が計算された。
ポリカプロラクトントリオール
1,1,1-トリス(ヒドロキシメチル)プロパン(7.4g)及びε-カプロラクトン(76g)を窒素下で3口フラスコ中で合わせ、均一になるまで150℃に加熱した。オクタン酸スズ(II)(0.83g)を5分間かけて添加したところ、180℃まで発熱した。フラスコを脱気し、窒素で3回パージし、その後窒素下で150℃で24時間撹拌した。冷却した反応混合物にヘキサン(3×300mL)を添加し、各添加後に上澄みをデカンテーションした。得られた粘稠な液体を真空下で40℃で乾燥させることで、低融点の白色固体(収量:80g)を得た。1H NMRによって1502g/molの分子量及び500g/molのヒドロキシル当量が計算された。
アクリルオキサゾリン官能性材料の調製
ジプロピレングリコールメチルエーテルアセテート(「DPMA」、31g)を窒素で15分間スパージングし、次いで130℃に加熱した。2-イソプロペニル-2-オキサゾリン(25g)、メタクリル酸n-ブチル(32g)、2,2’-アゾビス(2-メチルブチロニトリル)(5.2g)、亜リン酸トリフェニル(0.29g)、及びt-ドデシルメルカプタン(0.57g)の溶液を30分かけて滴下した。30分間撹拌した後、5mlのDPMA中の0.5gの2,2’-アゾビス(2-メチルブチロニトリル)を添加し、溶液をさらに30分間撹拌した。5mlのDPMA中の追加の0.5gの2,2’-アゾビス(2-メチルブチロニトリル)を添加し、溶液をさらに30分間撹拌した。その後、溶液を50℃まで冷却し、撹拌しながらヘキサン(0.5L)にゆっくり添加した。合わせた溶液を室温まで冷却した。溶媒をデカンテーションして粘稠な液体を得た。生成物をヘキサン(0.5L)に入れ、2回目のデカンテーションを行った。粗製固体生成物を50℃で真空下で乾燥した。収量: 45g。THF溶離液を使用してポリスチレン標準に対してGPCにより測定したMwは3610g/molであり、数平均分子量(Mn)は2120g/molであった。計算されたオキサゾリン当量は、1H NMRに基づいて292g/molであった。
実施例4~9
オキサゾリン官能性二次架橋剤を使用するフォトクロミックコーティング組成物を、表1に列挙されている成分を使用して調製した。全ての成分は、重量部として記載されている。表1に示されている各コーティング組成物については、チャージ1の成分を合わせ、50℃で最低30分間、又は固形分が溶解するまで加熱した。チャージ2を添加し、50℃で30分間撹拌を継続した。溶液を室温まで冷却し、続いてチャージ3を添加した。混合物を1時間撹拌し、続いてチャージ4を添加した。溶液は、使用前に室温で最低10時間撹拌した。全ての組成物は、30パーセントの理論上の固形分に処方した。
ポリカルボジイミド二次架橋剤を使用するフォトクロミック組成物は、上の実施例4~9の手順を使用して、表2に列挙されている成分を使用して調製した。両方の組成物は、30パーセントの理論上の固形分に処方した。
比較例1(CE1)は、2つのヒドロキシル基を有し且つ少なくとも15,000g/molのヒドロキシル当量を有する第1のポリオール(i)を含まない。CE1は、高ヒドロキシル当量TPUジオールの代わりの等モル量の低ヒドロキシル当量ジオールと、オキサゾリン官能性二次架橋剤とを使用して、実施例4~9について記載した通りに調製した。比較例2(CE2)は、二次架橋剤(c)、又は少なくとも3つのヒドロキシル基を有し且つ少なくとも300g/molのヒドロキシル当量を有する第2のポリオール(ii)を含まない。CE2は、ポリオール成分としてTPUジオールのみを含み且つ二次架橋剤を含まない処方を使用して、実施例4~9について記載した通りに調製した。処方の詳細を表3に示す。
実施例4~11、CE1及びCE2の組成物を、それぞれ76ミリメートルの直径を有するPDQ(登録商標)コーティングされたGentex(登録商標)ポリカーボネートプラノレンズに塗布した。コーティングの前に、各レンズを、100ワットの出力で3分間、毎分100ミリリットル(mL)の酸素の流量で酸素プラズマ処理した。各組成物約1~2mLを基材上に分配し、次いで、実施例4~11については0.6~0.65gのウェットコーティング(30パーセント固形分)、CE1については0.3~0.33gのウェットコーティング、及びCE2については0.9gのウェットコーティングをレンズ上に堆積させるのに十分なスピン速度で8秒間回転させた。
パート4a.微小硬度評価
一組の試験片を、105℃で3時間さらに熱硬化し、次いで、Fischer Technology,Inc.から入手可能なFischerscope HCV,Model H100SMCを使用して微小硬度試験を行った。硬度は、100ミリニュートンの荷重を15秒間加えた後、侵入深さ2ミクロンで測定した。各試験片を少なくとも2回測定した。得られたデータを平均化した。
試験片の2つ目の組を、前述のように酸素プラズマでさらに処理し、米国特許第7,410,691号明細書の実施例1の表1に報告されている処方に従って保護コーティングでスピンコーティングした。試験片を、D電球からのUV光を用いて窒素雰囲気下で硬化した。その後、各試験片を105℃で3時間熱硬化した。
微小硬度及びフォトクロミック性能の結果を表4に示す。飽和時のΔODは、活性化15分後であり、退色半減期(「T1/2」)値は、活性化光源を除去した後、コーティング中のフォトクロミック材料の活性化形態のΔODが73.4°F(23℃)で15分におけるΔODの半分に到達する秒単位の時間である。
一実施形態において、例えば、以下の項目が提供される。
(項目1)
(a)
(i)2つのヒドロキシル基を有し及び少なくとも15,000g/molのヒドロキシル当量を有する第1のポリオールと、
(ii)少なくとも3つのヒドロキシル基を有し及び少なくとも300g/molのヒドロキシル当量を有する、前記第1のポリオールとは異なる第2のポリオールと、
を含むポリオール成分、
(b)少なくとも3つの環状無水物基を有するポリ(無水物)、
(c)ポリ(カルボジイミド)、オキサゾリン官能性材料、及びこれらの混合物からなる群から選択される二次架橋剤、並びに
(d)フォトクロミック材料
を含有する、硬化性フォトクロミックコーティング組成物。
(項目2)
前記第1のポリオール(i)及び前記第2のポリオール(ii)が、ポリウレタンポリオール、ポリエーテルポリオール、ポリエステルポリオール、ポリカーボネートポリオール、アクリルポリオール、ポリシロキサンポリオール、ポリ(尿素)ウレタンポリオール、ポリアミドポリオール、これらのコポリマー、及びこれらの組み合わせからなる群からそれぞれ独立して選択される、項目1に記載の硬化性フォトクロミックコーティング組成物。
(項目3)
前記第1のポリオール(i)が75,000g/mol未満のヒドロキシル当量を有する、項目1又は2に記載の硬化性フォトクロミックコーティング組成物。
(項目4)
前記第1のポリオール(i)が熱可塑性ポリウレタンジオールを含む、項目1~3のいずれか一項に記載の硬化性フォトクロミックコーティング組成物。
(項目5)
前記第2のポリオール(ii)が、8,000g/mol未満のヒドロキシル当量を有する、項目1~4のいずれか一項に記載の硬化性フォトクロミックコーティング組成物。
(項目6)
前記第2のポリオール(ii)が、ポリ(カプロラクトン)トリオール、ポリ(カプロラクトン)テトラオール、ポリカーボネートトリオール、ポリカーボネートテトラオール、アクリルポリオール、又はこれらの混合物を含む、項目1~5のいずれか一項に記載の硬化性フォトクロミックコーティング組成物。
(項目7)
前記ポリ(無水物)(b)が1分子あたり少なくとも3つの環状無水物基を有する、項目1~6のいずれか一項に記載の硬化性フォトクロミックコーティング組成物。
(項目8)
前記ポリ(無水物)(b)が、
マレイン酸無水物とC 2 ~C 24 オレフィンとのコポリマー、
マレイン酸無水物と(メタ)アクリレートとのコポリマー、
マレイン酸無水物とスチレンとのコポリマー、
及びこれらの混合物からなる群から選択されるコポリマーを含む、項目1~7のいずれか一項に記載の硬化性フォトクロミックコーティング組成物。
(項目9)
前記ポリ(無水物)(b)が500~100,000g/molの範囲の数平均分子量を有する、項目1~8のいずれか一項に記載の硬化性フォトクロミックコーティング組成物。
(項目10)
前記二次架橋剤(c)が、少なくとも3つのオキサゾリン基を有するオキサゾリン官能性材料を含む、項目1~9のいずれか一項に記載の硬化性フォトクロミックコーティング組成物。
(項目11)
前記フォトクロミック材料(d)が、ナフトピラン、ベンゾピラン、インデノナフトピラン、インドールナフトピラン、フェナントロピラン、スピロピラン、オキサジン、水銀ジチオゾネート、フルギド、フルギミド、及びこれらの混合物からなる群から選択される、項目1~10のいずれか一項に記載の硬化性フォトクロミックコーティング組成物。
(項目12)
前記ポリ(無水物)(b)中に存在する無水物基の当量対前記ポリオール成分(a)中に存在するヒドロキシル基の当量の比が1:3~5:1の範囲である、項目1~11のいずれか一項に記載の硬化性フォトクロミックコーティング組成物。
(項目13)
(a)25~79.9重量パーセントのポリオール成分、
(b)10~55重量パーセントのポリ(無水物)、
(c)10~30重量パーセントの二次架橋剤、及び
(d)0.1~20重量パーセントのフォトクロミック化合物、
を含有するフォトクロミックコーティング組成物であって、前記重量パーセントが前記フォトクロミック組成物中に存在する総固形分基準である、項目1~12のいずれか一項に記載の硬化性フォトクロミックコーティング組成物。
(項目14)
項目1~13のいずれか一項に記載の硬化性フォトクロミックコーティング組成物を含む光学物品。
(項目15)
前記光学物品がレンズである、項目14に記載の光学物品。
Claims (14)
- (a)
(i)2つのヒドロキシル基を有し及び少なくとも15,000のヒドロキシル当量を有する第1のポリオールと、
(ii)少なくとも3つのヒドロキシル基を有し及び少なくとも300のヒドロキシル当量を有する、前記第1のポリオールとは異なる第2のポリオールと、
を含むポリオール成分、
(b)少なくとも3つの環状無水物基を有するポリ(カルボン酸無水物)、
(c)ポリ(カルボジイミド)、オキサゾリン官能性材料、及びこれらの混合物からなる群から選択される二次架橋剤、並びに
(d)フォトクロミック材料
を含有する、硬化性フォトクロミックコーティング組成物。 - 前記第1のポリオール(i)及び前記第2のポリオール(ii)が、ポリウレタンポリオール、ポリエーテルポリオール、ポリエステルポリオール、ポリカーボネートポリオール、アクリルポリオール、ポリシロキサンポリオール、ポリ(尿素)ウレタンポリオール、ポリアミドポリオール、これらのコポリマー、及びこれらの組み合わせからなる群からそれぞれ独立して選択される、請求項1に記載の硬化性フォトクロミックコーティング組成物。
- 前記第1のポリオール(i)が75,000未満のヒドロキシル当量を有する、請求項1又は2に記載の硬化性フォトクロミックコーティング組成物。
- 前記第1のポリオール(i)が熱可塑性ポリウレタンジオールを含む、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コーティング組成物。
- 前記第2のポリオール(ii)が、8,000未満のヒドロキシル当量を有する、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コーティング組成物。
- 前記第2のポリオール(ii)が、ポリ(カプロラクトン)トリオール、ポリ(カプロ
ラクトン)テトラオール、ポリカーボネートトリオール、ポリカーボネートテトラオール、アクリルポリオール、又はこれらの混合物を含む、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コーティング組成物。 - 前記ポリ(カルボン酸無水物)(b)が、
マレイン酸無水物とC2~C24オレフィンとのコポリマー、
マレイン酸無水物と(メタ)アクリレートとのコポリマー、
マレイン酸無水物とスチレンとのコポリマー、
及びこれらの混合物からなる群から選択されるコポリマーを含む、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コーティング組成物。 - 前記ポリ(カルボン酸無水物)(b)が500~100,000g/molの範囲の数平均分子量を有する、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コーティング組成物。
- 前記二次架橋剤(c)が、少なくとも3つのオキサゾリン基を有するオキサゾリン官能性材料を含む、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コーティング組成物。
- 前記フォトクロミック材料(d)が、ナフトピラン、ベンゾピラン、インデノナフトピラン、フェナントロピラン、スピロピラン、スピロオキサジン、水銀ジチゾネート、フルギド、フルギミド、及びこれらの混合物からなる群から選択される、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コーティング組成物。
- 前記ポリ(カルボン酸無水物)(b)中に存在する無水物基の当量対前記ポリオール成分(a)中に存在するヒドロキシル基の当量の比が1:3~5:1の範囲である、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コーティング組成物。
- (a)25~79.9重量パーセントのポリオール成分、
(b)10~55重量パーセントのポリ(カルボン酸無水物)、
(c)10~30重量パーセントの二次架橋剤、及び
(d)0.1~20重量パーセントのフォトクロミック化合物、
を含有するフォトクロミックコーティング組成物であって、前記重量パーセントが前記フォトクロミック組成物中に存在する総固形分基準である、請求項1~11のいずれか一項に記載の硬化性フォトクロミックコーティング組成物。 - 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コーティング組成物を含む光学物品。
- 前記光学物品がレンズである、請求項13に記載の光学物品。
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JP2008525181A (ja) | 2004-12-23 | 2008-07-17 | ピーピージー インダストリーズ オハイオ, インコーポレイテッド | 異なる基材材料を含む製品のための色調和コーティング |
WO2009051209A1 (ja) | 2007-10-18 | 2009-04-23 | Ajinomoto Co., Inc. | 樹脂組成物 |
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WO2021037374A1 (en) | 2021-03-04 |
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