CA2274541A1 - Retroreflective article having launderably durable bead-bond - Google Patents

Retroreflective article having launderably durable bead-bond

Info

Publication number
CA2274541A1
CA2274541A1 CA002274541A CA2274541A CA2274541A1 CA 2274541 A1 CA2274541 A1 CA 2274541A1 CA 002274541 A CA002274541 A CA 002274541A CA 2274541 A CA2274541 A CA 2274541A CA 2274541 A1 CA2274541 A1 CA 2274541A1
Authority
CA
Canada
Prior art keywords
retroreflective article
moieties
segments
bond
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.)
Granted
Application number
CA002274541A
Other languages
French (fr)
Other versions
CA2274541C (en
Inventor
Robert J. Fleming
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
The Minnesota Mining & Manufacturing Company
Robert J. Fleming
Minnesota Mining And Manufacturing Company
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
Application filed by The Minnesota Mining & Manufacturing Company, Robert J. Fleming, Minnesota Mining And Manufacturing Company filed Critical The Minnesota Mining & Manufacturing Company
Publication of CA2274541A1 publication Critical patent/CA2274541A1/en
Application granted granted Critical
Publication of CA2274541C publication Critical patent/CA2274541C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C08G18/61—Polysiloxanes
    • 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
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/913—Material designed to be responsive to temperature, light, moisture
    • 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.]
    • Y10T428/24355—Continuous and nonuniform or irregular surface on layer or component [e.g., roofing, etc.]
    • Y10T428/24372—Particulate 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
    • 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
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31598—Next to silicon-containing [silicone, cement, etc.] layer
    • Y10T428/31601—Quartz or glass

Abstract

A retroreflective article (10) has retroreflective elements (12) partially embedded in a binder layer (14) that contains a solid polyurethane. The polyurethane includes soft segments, hard segments, silicon moieties, and urethane moieties. The specific chemical identities and relative amounts of the segments and moieties are sufficient to impart desired high elongation and low modulus to the polymer.
The inventive retroreflective article is capable of demonstrating extraordinary laundering durability under industrial wash conditions and tumble and tunnel drying.
CA 2274541 1996-12-20 1997-12-04 Retroreflective article having launderably durable bead-bond Expired - Fee Related CA2274541C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/777,718 US5976669A (en) 1996-12-20 1996-12-20 Retroreflective article having launderably durable bead-bond
US08/777718 1996-12-20
PCT/US1997/023040 WO1998028642A1 (en) 1996-12-20 1997-12-04 Retroreflective article having launderably durable bead-bond

Publications (2)

Publication Number Publication Date
CA2274541A1 true CA2274541A1 (en) 1998-07-02
CA2274541C CA2274541C (en) 2007-02-06

Family

ID=25111044

Family Applications (1)

Application Number Title Priority Date Filing Date
CA 2274541 Expired - Fee Related CA2274541C (en) 1996-12-20 1997-12-04 Retroreflective article having launderably durable bead-bond

Country Status (10)

Country Link
US (1) US5976669A (en)
EP (1) EP0946889B1 (en)
JP (1) JP4344865B2 (en)
KR (1) KR100519884B1 (en)
CN (1) CN1113252C (en)
CA (1) CA2274541C (en)
DE (1) DE69721305T2 (en)
HK (1) HK1023408A1 (en)
TW (1) TW386092B (en)
WO (1) WO1998028642A1 (en)

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US6361850B1 (en) 1999-06-17 2002-03-26 3M Innovative Properties Company Retroreflective article having a colored layer containing a dye covalently bonded to a polymer
JP2003502707A (en) 1999-06-17 2003-01-21 スリーエム イノベイティブ プロパティズ カンパニー Retroreflective article having a reflective layer and a colored layer containing a dye covalently bonded to a polymer
FR2803724B1 (en) * 2000-01-18 2002-04-12 T 2 S LIGHT RETROREFLECTIVE AND / OR FLUORESCENT COMPLEX MATERIAL
US6676754B1 (en) 2000-06-30 2004-01-13 3M Innovative Properties Company Coating apparatus and methods of applying a polymer coating
US6723433B2 (en) * 2001-03-02 2004-04-20 3M Innovative Properties Company Printable film and coating composition exhibiting stain resistance
US6953624B2 (en) * 2001-03-02 2005-10-11 3M Innovative Properties Company Printable film and coating composition exhibiting stain resistance
ITMO20010126A1 (en) * 2001-06-21 2002-12-21 Autoadesivi S R L FABRIC OR THERMAL ADHESIVE REFLECTIVE OR REFLECTIVE
US6820280B1 (en) * 2002-06-18 2004-11-23 Blaver Manufacturing Company, Inc. Rip-off, high-visibility, safety vest
DE10355318A1 (en) * 2003-11-27 2005-06-23 Wacker-Chemie Gmbh Process for the preparation of organyloxysilyl-terminated polymers
WO2005066667A1 (en) * 2003-12-30 2005-07-21 3M Innovative Properties Company Color shifting retroreflector and method of making same
JP4750559B2 (en) * 2004-01-30 2011-08-17 株式会社カネカ Adhesive composition
US9198156B2 (en) * 2004-08-23 2015-11-24 Telefonaktiebolaget L M Ericsson (Publ) Paging mobile stations in a hybrid network
WO2006044305A1 (en) * 2004-10-15 2006-04-27 Dow Global Technologies Inc. An isocyanate-terminated prepolymer composition and a polyurethane or polyurea elastomer produced therefrom
US8232362B2 (en) * 2005-09-15 2012-07-31 Momentive Performance Materials Inc. Preparation of amino-silane terminated polymer by using organic bismuth catalyst and cured polymer therefrom by using non-tin catalyst
US9248470B2 (en) 2006-07-31 2016-02-02 Safe Reflections, Inc. Colorized retroreflective material and method
DE102006055739A1 (en) * 2006-11-25 2008-05-29 Bayer Materialscience Ag impression materials
US8292539B2 (en) * 2007-04-10 2012-10-23 Stoncor Group, Inc. Agglomerated retroreflective beads for highway marking and methods for fabrication and use thereof
US9207373B2 (en) 2007-04-10 2015-12-08 Stoncor Group, Inc. Methods for fabrication and highway marking usage of agglomerated retroreflective beads
CN101971061B (en) * 2008-01-10 2014-04-16 可隆工业株式会社 Optical sheets
JP2010131817A (en) * 2008-12-03 2010-06-17 Ito Kosan Kk Retroreflective sheet
WO2011147079A1 (en) 2010-05-25 2011-12-01 3M Innovative Properties Company Exposed lens retroreflective article
TW201315598A (en) * 2012-10-18 2013-04-16 Cing Wai Kung Mau Company Process for reflective products
CN103792603B (en) 2012-10-26 2016-07-06 3M创新有限公司 Retroreflecting material and goods
CN103792604B (en) 2012-10-26 2016-12-21 3M创新有限公司 Retroreflecting goods and appligue
WO2015030770A1 (en) 2013-08-29 2015-03-05 Safe Reflections, Inc. Colorized retroreflective material and method of formation
WO2015175024A2 (en) 2014-01-31 2015-11-19 3M Innovative Properties Company Colored retroreflective articles
JP6650148B2 (en) 2014-02-13 2020-02-19 スリーエム イノベイティブ プロパティズ カンパニー Dual cure type stain resistant microsphere article
EP3105047B1 (en) 2014-02-13 2020-12-09 3M Innovative Properties Company Flexible microsphere articles having high temperature stability
CN106574993B (en) * 2014-05-09 2022-07-12 3M创新有限公司 Retroreflective article
US10261222B2 (en) * 2014-06-16 2019-04-16 3M Innovative Properties Company Retroreflective articles with wash durable bead bond layers
JP6454096B2 (en) * 2014-06-27 2019-01-16 株式会社松井色素化学工業所 Image forming method and cloth-like fiber product
EP3201660A1 (en) 2014-09-30 2017-08-09 3M Innovative Properties Company Retroreflective colored articles
CN104354352A (en) * 2014-10-14 2015-02-18 陈国顺 Color printing type reflective fabric and production method thereof
CN107111018A (en) 2014-12-30 2017-08-29 3M创新有限公司 Antifouling retroreflective articles
US10844160B2 (en) 2015-02-13 2020-11-24 3M Innovative Properties Company Flexible microsphere articles having high temperature stability
EP3436259A4 (en) 2016-03-30 2020-02-05 3M Innovative Properties Company Article featuring a predetermined pattern of randomly distributed microspheres and methods of making the same
ITUA20164500A1 (en) * 2016-06-20 2017-12-20 Giorgio Corradi REFLECTIVE BACK INSERT
US20180055124A1 (en) * 2016-08-26 2018-03-01 Chieh-Yu Chen Hat
EP3701297A4 (en) 2017-10-27 2021-07-28 3M Innovative Properties Company Retroreflective article comprising retroreflective elements comprising primary reflective layers and secondary reflective layers
EP3701299A4 (en) 2017-10-27 2021-08-25 3M Innovative Properties Company Retroreflective article comprising locally-laminated reflective layers
KR20200076716A (en) 2017-10-27 2020-06-29 쓰리엠 이노베이티브 프로퍼티즈 캄파니 Retroreflective article comprising embedded reflective layer
US20220216616A1 (en) * 2019-05-24 2022-07-07 3M Innovative Properties Company Radar retroreflective article
US20230099542A1 (en) * 2021-09-29 2023-03-30 Douglas Bradshaw Traffic Control Safety Gloves

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Also Published As

Publication number Publication date
WO1998028642A1 (en) 1998-07-02
EP0946889B1 (en) 2003-04-23
HK1023408A1 (en) 2000-09-08
KR100519884B1 (en) 2005-10-12
JP2001507138A (en) 2001-05-29
JP4344865B2 (en) 2009-10-14
TW386092B (en) 2000-04-01
CN1113252C (en) 2003-07-02
DE69721305D1 (en) 2003-05-28
CN1240516A (en) 2000-01-05
DE69721305T2 (en) 2004-02-12
EP0946889A1 (en) 1999-10-06
CA2274541C (en) 2007-02-06
KR20000062254A (en) 2000-10-25
US5976669A (en) 1999-11-02

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Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20121204