CA2308253C - Stabilization of fluorescent dyes in vinyl articles using hindered amine light stabilizers - Google Patents

Stabilization of fluorescent dyes in vinyl articles using hindered amine light stabilizers Download PDF

Info

Publication number
CA2308253C
CA2308253C CA 2308253 CA2308253A CA2308253C CA 2308253 C CA2308253 C CA 2308253C CA 2308253 CA2308253 CA 2308253 CA 2308253 A CA2308253 A CA 2308253A CA 2308253 C CA2308253 C CA 2308253C
Authority
CA
Canada
Prior art keywords
article
hindered amine
fluorescent
amine light
dye
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.)
Expired - Fee Related
Application number
CA 2308253
Other languages
English (en)
French (fr)
Other versions
CA2308253A1 (en
Inventor
Kenneth M. White
Lee A. Pavelka
Vera L. Lightle
James C. Coderre
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
3M Co
Original Assignee
Minnesota Mining and Manufacturing Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25498098&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2308253(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Publication of CA2308253A1 publication Critical patent/CA2308253A1/en
Application granted granted Critical
Publication of CA2308253C publication Critical patent/CA2308253C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B44—DECORATIVE ARTS
    • B44F—SPECIAL DESIGNS OR PICTURES
    • B44F1/00—Designs or pictures characterised by special or unusual light effects
    • B44F1/08—Designs or pictures characterised by special or unusual light effects characterised by colour effects
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
    • B32B27/20—Layered products comprising a layer of synthetic resin characterised by the use of special additives using fillers, pigments, thixotroping agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B32B27/304—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising vinyl halide (co)polymers, e.g. PVC, PVDC, PVF, PVDF
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B3/00—Layered products comprising a layer with external or internal discontinuities or unevennesses, or a layer of non-planar shape; Layered products comprising a layer having particular features of form
    • B32B3/26—Layered products comprising a layer with external or internal discontinuities or unevennesses, or a layer of non-planar shape; Layered products comprising a layer having particular features of form characterised by a particular shape of the outline of the cross-section of a continuous layer; characterised by a layer with cavities or internal voids ; characterised by an apertured layer
    • B32B3/30—Layered products comprising a layer with external or internal discontinuities or unevennesses, or a layer of non-planar shape; Layered products comprising a layer having particular features of form characterised by a particular shape of the outline of the cross-section of a continuous layer; characterised by a layer with cavities or internal voids ; characterised by an apertured layer characterised by a layer formed with recesses or projections, e.g. hollows, grooves, protuberances, ribs
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B44—DECORATIVE ARTS
    • B44F—SPECIAL DESIGNS OR PICTURES
    • B44F1/00—Designs or pictures characterised by special or unusual light effects
    • B44F1/02—Designs or pictures characterised by special or unusual light effects produced by reflected light, e.g. matt surfaces, lustrous surfaces
    • B44F1/04—Designs or pictures characterised by special or unusual light effects produced by reflected light, e.g. matt surfaces, lustrous surfaces after passage through surface layers, e.g. pictures with mirrors on the back
    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • 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
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/002—Influencing the physical properties by treatment with an amine
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/12—Reflex reflectors
    • G02B5/122—Reflex reflectors cube corner, trihedral or triple reflector type
    • G02B5/124—Reflex reflectors cube corner, trihedral or triple reflector type plural reflecting elements forming part of a unitary plate or sheet
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/12—Reflex reflectors
    • G02B5/126—Reflex reflectors including curved refracting surface
    • G02B5/128—Reflex reflectors including curved refracting surface transparent spheres being embedded in matrix
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2250/00—Layers arrangement
    • B32B2250/02—2 layers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2250/00—Layers arrangement
    • B32B2250/24—All layers being polymeric
    • B32B2250/246—All polymers belonging to those covered by groups B32B27/32 and B32B27/30
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/40—Properties of the layers or laminate having particular optical properties
    • B32B2307/402—Coloured
    • B32B2307/4026—Coloured within the layer by addition of a colorant, e.g. pigments, dyes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/40—Properties of the layers or laminate having particular optical properties
    • B32B2307/416—Reflective
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/40—Properties of the layers or laminate having particular optical properties
    • B32B2307/42—Polarizing, birefringent, filtering
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/40—Properties of the layers or laminate having particular optical properties
    • B32B2307/422—Luminescent, fluorescent, phosphorescent
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2590/00—Signboards, advertising panels, road signs
    • 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.]
    • Y10T428/2419—Fold at edge
    • Y10T428/24198—Channel-shaped edge component [e.g., binding, 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
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24479—Structurally defined web or sheet [e.g., overall dimension, etc.] including variation in thickness
    • 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.]
    • Y10T428/24479—Structurally defined web or sheet [e.g., overall dimension, etc.] including variation in thickness
    • Y10T428/24612—Composite web or sheet
    • 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
    • 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
    • Y10T428/252—Glass or ceramic [i.e., fired or glazed clay, cement, etc.] [porcelain, quartz, 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
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • Y10T428/2993—Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]
    • Y10T428/2996—Glass particles or spheres
    • 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]
    • Y10T428/31678—Of metal
    • Y10T428/31692—Next to addition polymer from unsaturated monomers
    • Y10T428/31699—Ester, halide or nitrile of addition polymer
    • 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
    • Y10T428/31909—Next to second addition polymer from unsaturated monomers
    • Y10T428/31913—Monoolefin polymer
    • Y10T428/3192—Next to vinyl or vinylidene chloride polymer
    • 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
    • Y10T428/31909—Next to second addition polymer from unsaturated monomers
    • Y10T428/31928—Ester, halide or nitrile of addition polymer
    • 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
    • Y10T428/31935—Ester, halide or nitrile of addition polymer
    • 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
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/60—Nonwoven fabric [i.e., nonwoven strand or fiber material]
    • Y10T442/674—Nonwoven fabric with a preformed polymeric film or sheet
    • Y10T442/676—Vinyl polymer or copolymer sheet or film [e.g., polyvinyl chloride, polyvinylidene chloride, polyvinyl acetate, etc.]

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Laminated Bodies (AREA)
CA 2308253 1997-10-23 1998-02-24 Stabilization of fluorescent dyes in vinyl articles using hindered amine light stabilizers Expired - Fee Related CA2308253C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/956,332 1997-10-23
US08/956,332 US6110566A (en) 1997-10-23 1997-10-23 Stabilization of fluorescent dyes in vinyl articles using hindered amine light stabilizers
PCT/US1998/003577 WO1999020688A1 (en) 1997-10-23 1998-02-24 Stabilization of fluorescent dyes in vinyl articles using hindered amine light stabilizers

Publications (2)

Publication Number Publication Date
CA2308253A1 CA2308253A1 (en) 1999-04-29
CA2308253C true CA2308253C (en) 2007-05-22

Family

ID=25498098

Family Applications (1)

Application Number Title Priority Date Filing Date
CA 2308253 Expired - Fee Related CA2308253C (en) 1997-10-23 1998-02-24 Stabilization of fluorescent dyes in vinyl articles using hindered amine light stabilizers

Country Status (10)

Country Link
US (6) US6110566A (https=)
EP (1) EP1025156B1 (https=)
JP (2) JP2001520293A (https=)
KR (1) KR100518493B1 (https=)
CN (1) CN1139628C (https=)
AU (1) AU6666098A (https=)
CA (1) CA2308253C (https=)
DE (1) DE69809280T2 (https=)
TW (1) TW538123B (https=)
WO (1) WO1999020688A1 (https=)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4063472B2 (ja) * 2000-04-10 2008-03-19 日本カーバイド工業株式会社 印刷された再帰反射シート
US6110566A (en) * 1997-10-23 2000-08-29 3M Innovative Properties Company Stabilization of fluorescent dyes in vinyl articles using hindered amine light stabilizers
JP2002507511A (ja) 1998-01-21 2002-03-12 リフレキサイト・コーポレーション 長寿命ポリ塩化ビニル蛍光シ−ト材
GB9824314D0 (en) * 1998-11-06 1998-12-30 Clariant Int Ltd New hetercyclic compounds
US6511256B1 (en) 1999-05-27 2003-01-28 Avery Dennison Corporation Pavement marker with improved daytime visibility and fluorescent durability
US6472050B1 (en) 1999-12-30 2002-10-29 Avery Dennison Corporation Light stable fluorescent vinyl suitable for use as a highway retroreflective roll-up sign
US6533961B2 (en) * 2000-02-22 2003-03-18 3M Innovative Properties Company Durable fluorescent organic pigments and methods of making
JP3580761B2 (ja) * 2000-06-28 2004-10-27 日本特殊陶業株式会社 スパークプラグ
US6972147B1 (en) 2000-11-09 2005-12-06 Avery Dennison Corporation Fluorescent polymeric articles fabricated from U.V. light absorbing polymer
US6537679B1 (en) 2000-11-09 2003-03-25 Avery Dennison Corporation Fluorescent articles of glycol-modified polyethylene terephthalate
US6514594B1 (en) 2000-11-09 2003-02-04 Avery Dennison Corporation Fluorescent polymeric articles having screening layer formed from U.V. light absorbing polymer
US6531205B1 (en) 2001-02-14 2003-03-11 Avery Dennison Corporation Fluorescent yellow retroreflective sheeting
US6916492B2 (en) 2001-03-30 2005-07-12 Council Of Scientific & Industrial Research Natural nontoxic multicolor fluorescent protein dye from a marine invertebrate, compositions containing the said dye and its uses
DE10117303A1 (de) 2001-03-30 2002-10-31 Council Scient Ind Res Ein natürlicher Fluoreszenzfarbstoff, gewonnen aus einem marinen Invertebraten, Zusammensetzungen die diesen Farbstoff enthalten und ihre Verwendung
US6689391B2 (en) 2001-03-30 2004-02-10 Council Of Scientific & Industrial Research Natural non-polar fluorescent dye from a non-bioluminescent marine invertebrate, compositions containing the said dye and its uses
US6841236B2 (en) * 2001-08-20 2005-01-11 3M Innovative Properties Co. Articles containing thioxanthone dyes
WO2003016407A1 (en) * 2001-08-20 2003-02-27 3M Innovative Properties Company Thioxanthone dyes with improved solubility and a method of preparing 2-oxybenzanthrones as intermediate materials for making of these dyes
US6956122B2 (en) * 2001-09-05 2005-10-18 Council Of Scientific & Industrial Research Multiple fluorescent natural dye compound from a marine organism
US6683124B2 (en) 2001-09-27 2004-01-27 Clariant Finance (Bvi) Limited Fluorescent pigment compositions
CA2480526C (en) 2002-04-30 2010-10-05 Avery Dennison Corporation Fluorescent articles having multiple film layers
US7618709B2 (en) * 2002-04-30 2009-11-17 Avery Dennison Corporation Fluorescent articles having multiple film layers
US7264880B2 (en) * 2002-04-30 2007-09-04 Avery Dennison Corporation Fluorescent articles having multiple film layers
US20060134370A1 (en) * 2003-02-12 2006-06-22 Lowe Clifford A Article with fabric-backed decorative element and method of fabricating the same
AU2003901361A0 (en) * 2003-03-25 2003-04-10 Fluorotechnics Pty Limited Method of enhancing fluorescence
US7396579B2 (en) * 2003-05-15 2008-07-08 3M Innovative Properties Company Fluorescent red-orange retroreflective sheeting
US7118251B1 (en) * 2003-05-23 2006-10-10 Ilight Technologies, Inc. Illumination device for simulating channel letters
US20050013986A1 (en) * 2003-05-29 2005-01-20 Buechler Troy Raymond Optical brighteners for display panels
US20050154098A1 (en) * 2004-01-09 2005-07-14 Reflexite Corporation Fade-resistant fluorescent retroreflective articles
US7625501B2 (en) * 2004-05-18 2009-12-01 Ifire Ip Corporation Color-converting photoluminescent film
US20070008790A1 (en) * 2004-05-26 2007-01-11 Buechler Troy R Optical brighteners for display panels
US20060017183A1 (en) * 2004-07-20 2006-01-26 Yung Hua Chen Method for manufacturing optical fiber light guide badges
US20060026731A1 (en) * 2004-08-04 2006-02-09 Reemay, Inc. High visibility fabric and safety vest
RU2415885C2 (ru) * 2005-10-27 2011-04-10 Эйвери Деннисон Корпорейшн Флуоресцентное изделие, имеющее множество слоев
RU2497161C2 (ru) * 2008-01-14 2013-10-27 Эйвери Деннисон Корпорейшн Ретроотражатель для применения в прикладных задачах, связанных с сенсорными экранами, и в системах позиционирования
KR101926406B1 (ko) 2009-12-11 2018-12-07 넥스트 홀딩스 리미티드 터치 스크린용 위치 검출 시스템 및 이에 사용하는 프리즘 필름
CA2847546C (en) 2011-09-06 2017-05-09 The Sun Products Corporation Solid and liquid textile-treating compositions
EP2925933B1 (de) * 2012-11-28 2017-02-08 Evonik Röhm GmbH Neuartige strassenmarkierungen zur unterstützung der umfeldwahrnehmung von fahrzeugen
CN102942753B (zh) * 2012-12-05 2014-12-10 中国科学院长春应用化学研究所 一种改性聚氯乙烯的制备方法
KR102344621B1 (ko) 2015-07-17 2021-12-30 도레이 카부시키가이샤 색변환 조성물, 색변환 필름 그리고 그것을 포함하는 백라이트 유닛, 디스플레이 및 조명
CN105153588B (zh) * 2015-09-23 2017-12-15 杭州信凯实业有限公司 用于道路设施的塑料复合材料及其应用
KR102166306B1 (ko) * 2018-08-20 2020-10-15 주식회사 엘지화학 폴리카보네이트 수지 조성물 및 이를 포함하는 광학 성형품
US11473012B2 (en) * 2020-06-25 2022-10-18 Battle Sight Technologies, LLC Article of manufacture using an industrial or commercial manufacturing process, wherein the article of manufacture comprises an infrared (IR) phosphorescent material
CN112430393B (zh) * 2020-11-20 2022-11-18 广州辰东新材料有限公司 一种用于激光焊接的耐紫外热塑性聚酰胺复合材料及其制备方法
CN114316471A (zh) * 2021-12-31 2022-04-12 天津利安隆新材料股份有限公司 适用于硬质聚氯乙烯材料的复合光稳定剂、硬质聚氯乙烯材料及其制备方法
CN116084174B (zh) * 2023-03-03 2024-05-24 西安工程大学 同时掺杂荧光染料和光稳定剂的聚合物光纤及其制备方法

Family Cites Families (63)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3684348A (en) * 1970-09-29 1972-08-15 Rowland Dev Corp Retroreflective material
US3830682A (en) 1972-11-06 1974-08-20 Rowland Dev Corp Retroreflecting signs and the like with novel day-night coloration
US4025159A (en) * 1976-02-17 1977-05-24 Minnesota Mining And Manufacturing Company Cellular retroreflective sheeting
US4238384A (en) 1978-06-19 1980-12-09 Sandoz, Inc. Method of incorporating additives in polymeric materials
US4336092A (en) * 1980-03-24 1982-06-22 Allan Wasserman Retroreflective fiber and method of making same
US4720356A (en) 1982-03-22 1988-01-19 American Optical Corporation Photochromic composition resistant to fatigue
US4393094A (en) 1982-04-19 1983-07-12 Ford Motor Company Stabilization of electron beam curable compositions for improved exterior durability
US4477608A (en) 1982-08-20 1984-10-16 Ciba-Geigy Corporation Compositions containing graphite
US4505967A (en) * 1983-04-11 1985-03-19 Minnesota Mining And Manufacturing Company High-angularity retroreflective sheeting and method for manufacture
JP2617678B2 (ja) 1984-05-10 1997-06-04 三菱化学エムケーブイ 株式会社 農業用塩化ビニル系樹脂フィルム
US4763985A (en) * 1986-08-01 1988-08-16 Minnesota Mining And Manufacturing Company Retroreflective sheet with enhanced brightness
JPS63255594A (ja) 1987-04-13 1988-10-21 Ebara Corp タ−ボ分子ポンプ
JP2844339B2 (ja) 1988-07-05 1999-01-06 日本カーバイド工業株式会社 蛍光発色シート
JP2701371B2 (ja) * 1988-08-02 1998-01-21 三菱化学エムケーブイ株式会社 農業用塩化ビニル系樹脂蛍光フィルム
EP0360740B1 (de) * 1988-09-09 1994-06-22 Ciba-Geigy Ag Neue Stoffzusammensetzungen enthaltend Molybdändisulfid
US5004770A (en) 1988-10-19 1991-04-02 Ciba-Geigy Corporation Polymeric substrates stabilized with N-substituted hindered amines
JPH02147651U (https=) * 1989-05-09 1990-12-14
US5246991A (en) * 1989-05-23 1993-09-21 Sumitomo Chemical Company, Limited Polyvinyl chloride resin composition
DE3933903A1 (de) 1989-10-11 1991-04-18 Basf Ag Fluoreszenzpigmente
US5302497A (en) 1989-12-21 1994-04-12 Ciba-Geigy Corporation Photosensitive organic polymeric material containing UV absorbers
EP0436464A3 (en) * 1989-12-21 1991-10-09 Ciba-Geigy Ag Photosensitive organic material containing uv-absorbers
US5989453A (en) 1990-05-11 1999-11-23 Societe Nouvelle De Chimie Industrielle S.A. Process for the manufacture of pigments, especially fluorescent pigments
US5229882A (en) 1990-05-16 1993-07-20 Reflexite Corporation Colored retroreflective sheeting and method of making same
JPH0686715B2 (ja) * 1990-10-31 1994-11-02 日東紡績株式会社 セルロース系布帛の染色加工方法
ZA918849B (en) * 1990-12-06 1992-08-26 Minnesota Mining & Mfg Articles exhibiting durable fluorescence
US5135568A (en) 1991-01-30 1992-08-04 Rohm And Haas Company Method for improving fluorescent coatings
US5352753A (en) 1991-04-25 1994-10-04 Allergan, Inc. Ultraviolet light absorbing compounds, silicone compositions and methods for making same
US5238733A (en) * 1991-09-30 1993-08-24 Minnesota Mining And Manufacturing Company Stretchable nonwoven webs based on multi-layer blown microfibers
US5415911A (en) 1992-01-16 1995-05-16 Stimsonite Corporation Photoluminescent retroreflective sheeting
EP0597391B1 (en) 1992-11-09 1998-09-09 Central Glass Company, Limited Glass plate with ultraviolet absorbing multilayer coating
DE9216001U1 (de) * 1992-11-25 1993-01-14 Röhm GmbH, 6100 Darmstadt UV-geschützte Kunststoffplatte oder -folie mit UV-absorbierender Deckschicht
US5405675A (en) 1992-12-10 1995-04-11 Minnesota Mining And Manufacturing Company Embossed multilayer film
EP0608198A1 (de) * 1993-01-18 1994-07-27 Ciba-Geigy Ag Cyclische Diphenylacetonitrile als Stabilisatoren
US5272562A (en) 1993-02-05 1993-12-21 Minnesota Mining And Manufacturing Company Cube-corner retroreflective articles
EP0612796A1 (en) * 1993-02-23 1994-08-31 Ciba-Geigy Ag Stabilisation of organic pigments
KR100437958B1 (ko) * 1993-10-20 2004-08-25 미네소타 마이닝 앤드 매뉴팩춰링 캄파니 초가요성,역반사성입방체모서리를지닌복합시트및이의제조방법
US5450235A (en) * 1993-10-20 1995-09-12 Minnesota Mining And Manufacturing Company Flexible cube-corner retroreflective sheeting
JPH10504341A (ja) 1994-08-15 1998-04-28 チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド 安定化されたｐｖｄｃ含有ｐｖｃ
US5565151A (en) 1994-09-28 1996-10-15 Reflexite Corporation Retroreflective prism structure with windows formed thereon
KR100431164B1 (ko) * 1994-11-28 2004-09-16 미네소타 마이닝 앤드 매뉴팩춰링 캄파니 착색내구성및/또는형광내구성이우수한제품
EP0732387B1 (en) 1995-03-17 2003-01-29 Sumitomo Chemical Company, Limited Antifogging agent composition and agricultural film coated therewith
JP3390302B2 (ja) * 1995-03-17 2003-03-24 住化プラステック株式会社 防曇剤組成物および農業用フィルム
JPH0912814A (ja) 1995-06-27 1997-01-14 Kyodo Yakuhin Kk 塩化ビニル系樹脂組成物
JPH11511592A (ja) * 1995-08-28 1999-10-05 ミネソタ マイニング アンド マニュファクチャリング カンパニー 持続性のある蛍光ソーラコレクタ
US5920429A (en) 1995-09-29 1999-07-06 Minnesota Mining And Manufacturing Company Fluorescent dye blends
US5674622A (en) 1995-09-29 1997-10-07 Minnesota Mining And Manufacturing Company Fluorescent dye blends
US5672643A (en) 1995-09-29 1997-09-30 Minnesota Mining And Manufacturing Company Fluorescent dye blends
JP3612136B2 (ja) 1996-02-29 2005-01-19 三善加工株式会社 ポリオレフィン系樹脂組成物および積層フィルム
WO1997037252A1 (en) * 1996-04-01 1997-10-09 Reflexite Corporation A color-fast retroreflective structure
US6110566A (en) 1997-10-23 2000-08-29 3M Innovative Properties Company Stabilization of fluorescent dyes in vinyl articles using hindered amine light stabilizers
US6001936A (en) 1997-10-24 1999-12-14 3M Innovative Properties Company Dye enhanced durability through controlled dye environment
JP2002507511A (ja) 1998-01-21 2002-03-12 リフレキサイト・コーポレーション 長寿命ポリ塩化ビニル蛍光シ−ト材
US6511256B1 (en) 1999-05-27 2003-01-28 Avery Dennison Corporation Pavement marker with improved daytime visibility and fluorescent durability
US6472050B1 (en) 1999-12-30 2002-10-29 Avery Dennison Corporation Light stable fluorescent vinyl suitable for use as a highway retroreflective roll-up sign
US6533961B2 (en) 2000-02-22 2003-03-18 3M Innovative Properties Company Durable fluorescent organic pigments and methods of making
US6312132B1 (en) 2000-09-12 2001-11-06 3M Innovative Properties Company Fluorescent red article and retroreflective article made therefrom
US6514594B1 (en) 2000-11-09 2003-02-04 Avery Dennison Corporation Fluorescent polymeric articles having screening layer formed from U.V. light absorbing polymer
US6537679B1 (en) 2000-11-09 2003-03-25 Avery Dennison Corporation Fluorescent articles of glycol-modified polyethylene terephthalate
US20020102389A1 (en) 2000-12-01 2002-08-01 Nielsen Steven M. Retroreflective laminate comprising a tear resistant film
US6531205B1 (en) 2001-02-14 2003-03-11 Avery Dennison Corporation Fluorescent yellow retroreflective sheeting
US6531613B1 (en) 2001-08-20 2003-03-11 3M Innovative Properties Company Thioxanthone dyes with improved solubility
US7264880B2 (en) 2002-04-30 2007-09-04 Avery Dennison Corporation Fluorescent articles having multiple film layers
US20050154098A1 (en) 2004-01-09 2005-07-14 Reflexite Corporation Fade-resistant fluorescent retroreflective articles

Also Published As

Publication number Publication date
KR20010031358A (ko) 2001-04-16
US6526588B2 (en) 2003-03-04
US7468406B2 (en) 2008-12-23
JP5280663B2 (ja) 2013-09-04
CN1278841A (zh) 2001-01-03
US20030104235A1 (en) 2003-06-05
CN1139628C (zh) 2004-02-25
US20050213213A1 (en) 2005-09-29
US20020090530A1 (en) 2002-07-11
KR100518493B1 (ko) 2005-10-05
US6406798B2 (en) 2002-06-18
US6110566A (en) 2000-08-29
DE69809280D1 (de) 2002-12-12
US20010046607A1 (en) 2001-11-29
DE69809280T2 (de) 2003-09-18
WO1999020688A1 (en) 1999-04-29
JP2008063579A (ja) 2008-03-21
AU6666098A (en) 1999-05-10
JP2001520293A (ja) 2001-10-30
CA2308253A1 (en) 1999-04-29
TW538123B (en) 2003-06-21
EP1025156A1 (en) 2000-08-09
EP1025156B1 (en) 2002-11-06
US7449514B2 (en) 2008-11-11
US20060292347A1 (en) 2006-12-28

Similar Documents

Publication Publication Date Title
CA2308253C (en) Stabilization of fluorescent dyes in vinyl articles using hindered amine light stabilizers
US5605761A (en) Articles exhibiting durable color containing a polycarbonate, a fluorescent dye and an amine light stabilizer
JP4610330B2 (ja) 多重フィルム層を有する蛍光物品
KR20160140751A (ko) 변색 물질
KR20120014203A (ko) 다중 필름층을 갖는 내구성을 가진 형광 물품
US20080032101A1 (en) Multilayer UV resistant thermoplastic composition
US6537679B1 (en) Fluorescent articles of glycol-modified polyethylene terephthalate
EP1951529B1 (en) Fluorescent article having multiple layers
US10078162B2 (en) Retroreflective material
MXPA00003890A (en) Stabilization of fluorescent dyes in vinyl articles using hindered amine light stabilizers
MXPA97003689A (en) Articles that present fluorescent and / or durab color properties

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20150224