JP2005500422A - チオキサントン染料を含有する物品 - Google Patents
チオキサントン染料を含有する物品 Download PDFInfo
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- JP2005500422A JP2005500422A JP2003521711A JP2003521711A JP2005500422A JP 2005500422 A JP2005500422 A JP 2005500422A JP 2003521711 A JP2003521711 A JP 2003521711A JP 2003521711 A JP2003521711 A JP 2003521711A JP 2005500422 A JP2005500422 A JP 2005500422A
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- Japan
- Prior art keywords
- article
- carbon atoms
- pigment
- alkyl group
- retroreflective
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000975 dye Substances 0.000 title description 72
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 title description 2
- 239000000049 pigment Substances 0.000 claims abstract description 96
- 239000003973 paint Substances 0.000 claims abstract description 28
- 239000003086 colorant Substances 0.000 claims abstract description 19
- 229920000642 polymer Polymers 0.000 claims description 75
- 239000000203 mixture Substances 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 54
- 239000011159 matrix material Substances 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 239000011230 binding agent Substances 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 229920005989 resin Polymers 0.000 claims description 39
- 239000011347 resin Substances 0.000 claims description 39
- 239000002245 particle Substances 0.000 claims description 38
- 239000000463 material Substances 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 28
- 239000000758 substrate Substances 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 229920000515 polycarbonate Polymers 0.000 claims description 16
- 239000004417 polycarbonate Substances 0.000 claims description 16
- 239000008199 coating composition Substances 0.000 claims description 14
- 239000004814 polyurethane Substances 0.000 claims description 14
- 229920002635 polyurethane Polymers 0.000 claims description 14
- 229920000728 polyester Polymers 0.000 claims description 13
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229920001577 copolymer Polymers 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 9
- 239000004005 microsphere Substances 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
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- 239000004800 polyvinyl chloride Substances 0.000 claims description 6
- 229920001169 thermoplastic Polymers 0.000 claims description 6
- 239000004611 light stabiliser Substances 0.000 claims description 5
- 229920000098 polyolefin Polymers 0.000 claims description 5
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 5
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004925 Acrylic resin Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000011324 bead Substances 0.000 claims description 4
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- 239000004645 polyester resin Substances 0.000 claims description 4
- 229920001187 thermosetting polymer Polymers 0.000 claims description 4
- DRLRGHZJOQGQEC-UHFFFAOYSA-N 2-(2-methoxypropoxy)propyl acetate Chemical compound COC(C)COC(C)COC(C)=O DRLRGHZJOQGQEC-UHFFFAOYSA-N 0.000 claims description 3
- 229920000178 Acrylic resin Polymers 0.000 claims description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 229920002959 polymer blend Polymers 0.000 claims description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical group CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000000945 filler Substances 0.000 claims 1
- 238000007789 sealing Methods 0.000 claims 1
- 239000004634 thermosetting polymer Substances 0.000 claims 1
- -1 thioxanthone compound Chemical class 0.000 abstract description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000010408 film Substances 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- 239000010410 layer Substances 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 18
- 239000007850 fluorescent dye Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- 239000000853 adhesive Substances 0.000 description 13
- 230000001070 adhesive effect Effects 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 235000010288 sodium nitrite Nutrition 0.000 description 8
- ITBGZUGEUXKCDK-UHFFFAOYSA-N 10-methoxy-8-thiahexacyclo[10.10.2.02,7.09,23.013,18.020,24]tetracosa-1(23),2,4,6,9,11,13,15,17,20(24),21-undecaen-19-one Chemical compound C1=CC=C[C]2SC(C(OC)=CC=3C4=C(C(=O)[C]5C=CC=CC5=3)C=C3)=C4C3=C21 ITBGZUGEUXKCDK-UHFFFAOYSA-N 0.000 description 7
- MGCJHKZGEWMKAY-UHFFFAOYSA-N 2-hydroxybenzo[b]phenalen-7-one Chemical compound C1=CC2=CC(O)=CC(C=3C(=CC=CC=3)C3=O)=C2C3=C1 MGCJHKZGEWMKAY-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 7
- 230000002411 adverse Effects 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 0 *c(cc1C2)ccc1-c1cc(*)cc3cccc2c13 Chemical compound *c(cc1C2)ccc1-c1cc(*)cc3cccc2c13 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000002671 adjuvant Substances 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 238000001125 extrusion Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 229910003460 diamond Inorganic materials 0.000 description 5
- 239000010432 diamond Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- LAVARTIQQDZFNT-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-yl acetate Chemical compound COCC(C)OCC(C)OC(C)=O LAVARTIQQDZFNT-UHFFFAOYSA-N 0.000 description 4
- OHSBCRWSUFDAAT-UHFFFAOYSA-N 10-(2,6-dimethylheptan-4-yloxy)-8-thiahexacyclo[10.10.2.02,7.09,23.013,18.020,24]tetracosa-1(23),2,4,6,9,11,13,15,17,20(24),21-undecaen-19-one Chemical compound C1=CC=C[C]2SC(C(OC(CC(C)C)CC(C)C)=CC=3C4=C(C(=O)[C]5C=CC=CC5=3)C=C3)=C4C3=C21 OHSBCRWSUFDAAT-UHFFFAOYSA-N 0.000 description 4
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 4
- 229920003313 Bynel® Polymers 0.000 description 4
- 229920001634 Copolyester Polymers 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 239000011358 absorbing material Substances 0.000 description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
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- 238000004809 thin layer chromatography Methods 0.000 description 4
- 230000000007 visual effect Effects 0.000 description 4
- JPDRAVYVMNMFAH-UHFFFAOYSA-N 1-(2-oxopropyl)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CC(=O)C JPDRAVYVMNMFAH-UHFFFAOYSA-N 0.000 description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 3
- CVDZIHNSBANSKT-UHFFFAOYSA-N 2-(2-ethylhexoxy)benzo[b]phenalen-7-one Chemical compound C1=CC2=CC(OCC(CC)CCCC)=CC(C=3C(=CC=CC=3)C3=O)=C2C3=C1 CVDZIHNSBANSKT-UHFFFAOYSA-N 0.000 description 3
- XAEDEURWSJGBQC-UHFFFAOYSA-N 3-(2-aminophenyl)sulfanyl-2-(2-ethylhexoxy)benzo[b]phenalen-7-one Chemical compound CCCCC(CC)COC1=CC(=C23)C4=CC=CC=C4C(=O)C3=CC=CC2=C1SC1=CC=CC=C1N XAEDEURWSJGBQC-UHFFFAOYSA-N 0.000 description 3
- NSAWFEANYZSYDY-UHFFFAOYSA-N 3-bromo-2-(2-ethylhexoxy)benzo[b]phenalen-7-one Chemical compound C1=CC2=C(Br)C(OCC(CC)CCCC)=CC(C=3C(=CC=CC=3)C3=O)=C2C3=C1 NSAWFEANYZSYDY-UHFFFAOYSA-N 0.000 description 3
- SPARVCBZIGSCJO-UHFFFAOYSA-N 6-n-octyloxy-14h-anthra(2,1,9mna)thioxanthene-14-one Chemical compound C1=CC=C[C]2SC(C(OCCCCCCCC)=CC=3C4=C(C(=O)[C]5C=CC=CC5=3)C=C3)=C4C3=C21 SPARVCBZIGSCJO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- 239000006057 Non-nutritive feed additive Substances 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
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- LKZZYVKEDGBRTB-UHFFFAOYSA-N 10,12-dihydrobenzo[a]thioxanthen-9-one Chemical class C1=CC2=CC=CC=C2C2=C1SC1=CC(=O)CC=C1C2 LKZZYVKEDGBRTB-UHFFFAOYSA-N 0.000 description 2
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- GIOPBGVECSDBEM-UHFFFAOYSA-N 3-(2-aminophenyl)sulfanyl-2-(2,6-dimethylheptan-4-yloxy)benzo[b]phenalen-7-one Chemical compound CC(C)CC(CC(C)C)OC1=CC(=C23)C4=CC=CC=C4C(=O)C3=CC=CC2=C1SC1=CC=CC=C1N GIOPBGVECSDBEM-UHFFFAOYSA-N 0.000 description 2
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/14—Benzoxanthene dyes; Benzothioxanthene dyes
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
- Y10T428/24893—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] including particulate material
- Y10T428/24901—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] including particulate material including coloring matter
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/25—Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31507—Of polycarbonate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31931—Polyene monomer-containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/934,427 US6841236B2 (en) | 2001-08-20 | 2001-08-20 | Articles containing thioxanthone dyes |
| PCT/US2002/015530 WO2003016391A2 (en) | 2001-08-20 | 2002-05-13 | Articles containing thioxanthone dyes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005500422A true JP2005500422A (ja) | 2005-01-06 |
| JP2005500422A5 JP2005500422A5 (enExample) | 2006-01-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003521711A Pending JP2005500422A (ja) | 2001-08-20 | 2002-05-13 | チオキサントン染料を含有する物品 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6841236B2 (enExample) |
| EP (1) | EP1423470B1 (enExample) |
| JP (1) | JP2005500422A (enExample) |
| KR (1) | KR100833636B1 (enExample) |
| AT (1) | ATE320470T1 (enExample) |
| DE (1) | DE60209905T2 (enExample) |
| WO (1) | WO2003016391A2 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10163344B4 (de) * | 2001-12-21 | 2006-01-19 | Papierfabrik Schoeller & Hoesch Gmbh & Co. Kg | Lichtbeständiges Overlaypapier, Verfahren zu dessen Herstellung und Verwendung desselben |
| US7396579B2 (en) * | 2003-05-15 | 2008-07-08 | 3M Innovative Properties Company | Fluorescent red-orange retroreflective sheeting |
| US9207373B2 (en) | 2007-04-10 | 2015-12-08 | Stoncor Group, Inc. | Methods for fabrication and highway marking usage of agglomerated retroreflective beads |
| US8292539B2 (en) * | 2007-04-10 | 2012-10-23 | Stoncor Group, Inc. | Agglomerated retroreflective beads for highway marking and methods for fabrication and use thereof |
| CN108504081B (zh) * | 2018-04-17 | 2020-09-01 | 三河市中益明晟科技有限公司 | 一种夜光弹性塑胶跑道、健步道及其制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1293939B (de) | 1965-03-06 | 1969-04-30 | Hoechst Ag | Verfahren zur Herstellung von Farbstoffen |
| DE2104718A1 (de) | 1971-02-02 | 1972-09-14 | Hoechst Ag | Polyesterharze und deren Verwendung in Tagesleuchtpigmenten |
| DE2134518C3 (de) | 1971-07-10 | 1979-08-16 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Verbindungen der Benzothloxanthenreihe |
| CH574436A5 (enExample) | 1971-07-10 | 1976-04-15 | Hoechst Ag | |
| IT1039349B (it) | 1975-06-24 | 1979-12-10 | Montedison Spa | Metodo per la preparazione del 2 idrossibenzantrone e dei suoi derivati di sostituzione |
| DE2613493A1 (de) | 1976-03-30 | 1977-10-06 | Hoechst Ag | Gefaerbte polyester, verfahren zu ihrer herstellung und ihre verwendung zum faerben von kunststoffen |
| DE2815031A1 (de) | 1978-04-07 | 1979-10-18 | Hoechst Ag | Verwendung von farbstoffen zur fluoreszenz-aktivierten helligkeitsverstaerkung |
| CH666487A5 (de) | 1986-05-26 | 1988-07-29 | Ciba Geigy Ag | Benzanthronlactone und verfahren zu ihrer herstellung. |
| GB8819387D0 (en) | 1988-08-15 | 1988-09-14 | Merck Patent Gmbh | Liquid crystal display devices & liquid crystal medium to be used therein |
| DE4041853A1 (de) | 1990-12-24 | 1992-06-25 | Cassella Ag | Verfahren zur herstellung von benzothioxanthen-farbstoffen |
| DE4202911A1 (de) | 1992-02-01 | 1993-08-05 | Cassella Ag | Farbstoffmischungen zum faerben von textilen hydrophoben fasermaterialien |
| JPH10308278A (ja) | 1997-05-08 | 1998-11-17 | Mitsubishi Chem Corp | 有機電界発光素子 |
| JPH10312885A (ja) | 1997-05-14 | 1998-11-24 | Mitsubishi Chem Corp | 有機電界発光素子 |
| US6110566A (en) | 1997-10-23 | 2000-08-29 | 3M Innovative Properties Company | Stabilization of fluorescent dyes in vinyl articles using hindered amine light stabilizers |
| US6531613B1 (en) * | 2001-08-20 | 2003-03-11 | 3M Innovative Properties Company | Thioxanthone dyes with improved solubility |
-
2001
- 2001-08-20 US US09/934,427 patent/US6841236B2/en not_active Expired - Fee Related
-
2002
- 2002-05-13 DE DE2002609905 patent/DE60209905T2/de not_active Expired - Fee Related
- 2002-05-13 WO PCT/US2002/015530 patent/WO2003016391A2/en not_active Ceased
- 2002-05-13 EP EP02736905A patent/EP1423470B1/en not_active Expired - Lifetime
- 2002-05-13 JP JP2003521711A patent/JP2005500422A/ja active Pending
- 2002-05-13 AT AT02736905T patent/ATE320470T1/de not_active IP Right Cessation
- 2002-05-13 KR KR1020047002318A patent/KR100833636B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003016391A2 (en) | 2003-02-27 |
| KR100833636B1 (ko) | 2008-05-30 |
| EP1423470B1 (en) | 2006-03-15 |
| DE60209905T2 (de) | 2006-10-19 |
| WO2003016391A3 (en) | 2003-12-04 |
| US20030077451A1 (en) | 2003-04-24 |
| EP1423470A2 (en) | 2004-06-02 |
| KR20040043195A (ko) | 2004-05-22 |
| DE60209905D1 (de) | 2006-05-11 |
| ATE320470T1 (de) | 2006-04-15 |
| US6841236B2 (en) | 2005-01-11 |
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