CA2268259C - Article comprising a flexible retroreflective sheeting - Google Patents
Article comprising a flexible retroreflective sheeting Download PDFInfo
- Publication number
- CA2268259C CA2268259C CA 2268259 CA2268259A CA2268259C CA 2268259 C CA2268259 C CA 2268259C CA 2268259 CA2268259 CA 2268259 CA 2268259 A CA2268259 A CA 2268259A CA 2268259 C CA2268259 C CA 2268259C
- Authority
- CA
- Canada
- Prior art keywords
- weight
- adhesive
- article
- sheeting
- parts
- 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
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- FEHYCIQPPPQNMI-UHFFFAOYSA-N ethenyl(triphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(C=C)OC1=CC=CC=C1 FEHYCIQPPPQNMI-UHFFFAOYSA-N 0.000 description 1
- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 0.000 description 1
- JEWCZPTVOYXPGG-UHFFFAOYSA-N ethenyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)C=C JEWCZPTVOYXPGG-UHFFFAOYSA-N 0.000 description 1
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- 239000002648 laminated material Substances 0.000 description 1
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- 239000000314 lubricant Substances 0.000 description 1
- 238000011326 mechanical measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QRWZCJXEAOZAAW-UHFFFAOYSA-N n,n,2-trimethylprop-2-enamide Chemical compound CN(C)C(=O)C(C)=C QRWZCJXEAOZAAW-UHFFFAOYSA-N 0.000 description 1
- JMCVCHBBHPFWBF-UHFFFAOYSA-N n,n-diethyl-2-methylprop-2-enamide Chemical compound CCN(CC)C(=O)C(C)=C JMCVCHBBHPFWBF-UHFFFAOYSA-N 0.000 description 1
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
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- 231100000719 pollutant Toxicity 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
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- 229920005668 polycarbonate resin Polymers 0.000 description 1
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- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
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- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
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- 239000004800 polyvinyl chloride Substances 0.000 description 1
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Classifications
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- 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
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
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- 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
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- 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
-
- 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
-
- 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
- Y10T156/00—Adhesive bonding and miscellaneous chemical manufacture
- Y10T156/10—Methods of surface bonding and/or assembly therefor
- Y10T156/1002—Methods of surface bonding and/or assembly therefor with permanent bending or reshaping or surface deformation of self sustaining lamina
- Y10T156/1028—Methods of surface bonding and/or assembly therefor with permanent bending or reshaping or surface deformation of self sustaining lamina by bending, drawing or stretch forming sheet to assume shape of configured lamina while in contact therewith
- Y10T156/1031—Methods of surface bonding and/or assembly therefor with permanent bending or reshaping or surface deformation of self sustaining lamina by bending, drawing or stretch forming sheet to assume shape of configured lamina while in contact therewith with preshaping of lamina
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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
- Y10T428/24—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.]
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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
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24628—Nonplanar uniform thickness material
-
- 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
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
-
- 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
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
-
- 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
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
- Y10T428/2878—Adhesive compositions including addition polymer from unsaturated monomer
-
- 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
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
- Y10T428/2878—Adhesive compositions including addition polymer from unsaturated monomer
- Y10T428/2891—Adhesive compositions including addition polymer from unsaturated monomer including addition polymer from alpha-beta unsaturated carboxylic acid [e.g., acrylic acid, methacrylic acid, etc.] Or derivative thereof
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
- Laminated Bodies (AREA)
- Optical Elements Other Than Lenses (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73572496A | 1996-10-23 | 1996-10-23 | |
| US08/735724 | 1996-10-23 | ||
| US87989797A | 1997-06-20 | 1997-06-20 | |
| US08/879897 | 1997-06-20 | ||
| PCT/US1997/015125 WO1998017466A1 (en) | 1996-10-23 | 1997-08-28 | Article comprising a flexible retroreflective sheeting |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2268259A1 CA2268259A1 (en) | 1998-04-30 |
| CA2268259C true CA2268259C (en) | 2006-07-04 |
Family
ID=27112937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2268259 Expired - Fee Related CA2268259C (en) | 1996-10-23 | 1997-08-28 | Article comprising a flexible retroreflective sheeting |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6677030B2 (2) |
| EP (1) | EP0934156B1 (2) |
| JP (1) | JP2001508367A (2) |
| KR (1) | KR100505207B1 (2) |
| CN (1) | CN1091409C (2) |
| AU (1) | AU717961B2 (2) |
| CA (1) | CA2268259C (2) |
| DE (1) | DE69723454T2 (2) |
| WO (1) | WO1998017466A1 (2) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111060994A (zh) * | 2019-12-18 | 2020-04-24 | 京东方科技集团股份有限公司 | 防眩光膜与显示面板 |
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| JP4521520B2 (ja) * | 2003-08-06 | 2010-08-11 | 綜研化学株式会社 | 低極性フィルム用粘着剤 |
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| CN112099120B (zh) * | 2020-09-15 | 2022-05-24 | 浙江夜光明光电科技股份有限公司 | 一种超柔软型反光布及其制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3551025A (en) | 1969-03-28 | 1970-12-29 | Minnesota Mining & Mfg | Highly flexible reflex reflecting constructions |
| US3725115A (en) | 1970-06-18 | 1973-04-03 | Ppg Industries Inc | Pressure-sensitive adhesive articles and method of making same |
| US4418120A (en) | 1982-07-19 | 1983-11-29 | Minnesota Mining And Manufacturing Co. | Tackified crosslinked acrylic adhesives |
| DE3339485A1 (de) | 1983-10-31 | 1985-05-15 | Wikolin Polymer Chemie Gmbh, 2800 Bremen | Strahlungshaertbare zusammensetzung und verfahren zu ihrer herstellung und verwendung |
| DE3563632D1 (en) | 1984-02-13 | 1988-08-11 | Takeda Chemical Industries Ltd | Method of adhesion and composition therefor |
| US4943139A (en) | 1988-09-19 | 1990-07-24 | Minnesota Mining And Manufacturing Company | Spoked wheel reflector employing encapsulated retroreflective tubing |
| US5069964A (en) | 1989-05-23 | 1991-12-03 | Minnesota Mining And Manufacturing Company | Flexible, substrate-insular retroreflective sheeting |
| US5223312A (en) | 1990-01-05 | 1993-06-29 | Langille John D | Multiple retroreflective striping method and structure |
| US5110655A (en) * | 1990-10-17 | 1992-05-05 | Minnesota Mining And Manufacturing Company | Removable, high temperature resistant retroreflective marking material |
| US5450235A (en) | 1993-10-20 | 1995-09-12 | Minnesota Mining And Manufacturing Company | Flexible cube-corner retroreflective sheeting |
| ES2119357T3 (es) | 1993-10-20 | 1998-10-01 | Minnesota Mining & Mfg | Estructuras laminares compuestas de esquinas cubicas retrorreflectoras ultraflexibles y metodos de fabricacion. |
| US5683798A (en) | 1993-11-10 | 1997-11-04 | Minnesota Mining And Manufacturing Company | Tackified pressure sensitive adhesives |
| CN1170424A (zh) * | 1994-12-20 | 1998-01-14 | 美国3M公司 | 逆向反射片制品 |
| RU2154578C2 (ru) * | 1995-02-16 | 2000-08-20 | Миннесота Майнинг Энд Мэнюфекчуринг Компани | Изделие, содержащее эффективный при кратковременном прижатии клей, имеющее улучшенную адгезию к пластифицированному поливинилхлориду, и способ соединения пластифицированного пвх с основой с помощью эффективного при кратковременном прижатии клея (его варианты) |
| US5874143A (en) * | 1996-02-26 | 1999-02-23 | Minnesota Mining And Manufacturing Company | Pressure sensitive adhesives for use on low energy surfaces |
| US5805338A (en) | 1996-04-10 | 1998-09-08 | Minnesota Minning And Manufacturing Company | Pillowed flexible cube-corner sheeting and methods of manufacture |
-
1997
- 1997-08-28 KR KR10-1999-7003477A patent/KR100505207B1/ko not_active Expired - Lifetime
- 1997-08-28 WO PCT/US1997/015125 patent/WO1998017466A1/en not_active Ceased
- 1997-08-28 JP JP51934498A patent/JP2001508367A/ja not_active Ceased
- 1997-08-28 EP EP97939611A patent/EP0934156B1/en not_active Expired - Lifetime
- 1997-08-28 CN CN97198944A patent/CN1091409C/zh not_active Expired - Lifetime
- 1997-08-28 CA CA 2268259 patent/CA2268259C/en not_active Expired - Fee Related
- 1997-08-28 DE DE1997623454 patent/DE69723454T2/de not_active Expired - Lifetime
- 1997-08-28 AU AU41658/97A patent/AU717961B2/en not_active Ceased
-
2001
- 2001-04-05 US US09/826,989 patent/US6677030B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111060994A (zh) * | 2019-12-18 | 2020-04-24 | 京东方科技集团股份有限公司 | 防眩光膜与显示面板 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20030136510A1 (en) | 2003-07-24 |
| CN1233997A (zh) | 1999-11-03 |
| WO1998017466A1 (en) | 1998-04-30 |
| US6677030B2 (en) | 2004-01-13 |
| CA2268259A1 (en) | 1998-04-30 |
| AU4165897A (en) | 1998-05-15 |
| CN1091409C (zh) | 2002-09-25 |
| EP0934156B1 (en) | 2003-07-09 |
| JP2001508367A (ja) | 2001-06-26 |
| AU717961B2 (en) | 2000-04-06 |
| KR20000052689A (ko) | 2000-08-25 |
| DE69723454T2 (de) | 2004-05-13 |
| DE69723454D1 (de) | 2003-08-14 |
| KR100505207B1 (ko) | 2005-08-03 |
| EP0934156A1 (en) | 1999-08-11 |
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