Polymethylmethacrylate based hardcoat composition and coated article

Title: Polymethylmethacrylate based hardcoat composition and coated article

Abstract

A coating composition is disclosed. The coating composition includes a poly(methyl methacrylate) polymer or copolymer having a weight average molecular weight of at least 50,000 grams per mole; monomer comprising at least one of an alkylene diacrylate, alkylene dimethacrylate, cycloalkylene diacrylate, or cycloalkylenedimethacrylate, wherein the at least one of an alkylene diacrylate, alkylene dimethacrylate, cycloalkylene diacrylate, or cycloalkylenedimethacrylate provides at least 80 percent by weight of the monomer; and a stabilizer against ultraviolet light. An article including a coating on a surface of a substrate and a method of making the article are also disclosed. The coating on the surface of the substrate is obtained by curing the disclosed coating composition.

Inventors:: Clear, Susannah C.; Padiyath, Raghunath; Lachmansingh, Garry W.; Strobel, Mark A.; Mackey, Sonja S.; Jing, Naiyong

Issue Date:: 2018-09-11

Research Org.:: 3M Innovative Properties Company, St. Paul, MN, (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1480291

Patent Number(s):: 10072173

Application Number:: 14/387,072

Assignee:: 3M Innovative Properties Company (St. Paul, MN)

Patent Classifications (CPCs):: C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08K - Use of inorganic or non-macromolecular organic substances as compounding ingredients

C - CHEMISTRY C09 - DYES C09D - COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS

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C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08K - Use of inorganic or non-macromolecular organic substances as compounding ingredients
C08K3/36 - Silica

C - CHEMISTRY C09 - DYES C09D - COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS
C09D4/06 - {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00

C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08K - Use of inorganic or non-macromolecular organic substances as compounding ingredients
C08K5/3435 - Piperidines

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y10 - TECHNICAL SUBJECTS COVERED BY FORMER USPC Y10T - TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
Y10T428/3154 - Of fluorinated addition polymer from unsaturated monomers
Y10T428/31507 - Of polycarbonate
Y10T428/31938 - Polymer of monoethylenically unsaturated hydrocarbon

C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08L - COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
C08L2312/00 - Crosslinking

C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08K - Use of inorganic or non-macromolecular organic substances as compounding ingredients
C08K5/3492 - Triazines

C - CHEMISTRY C09 - DYES C09D - COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS
C09D133/12 - Homopolymers or copolymers of methyl methacrylate
C09D7/48 - Stabilisers against degradation by oxygen, light or heat

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y10 - TECHNICAL SUBJECTS COVERED BY FORMER USPC Y10T - TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
Y10T428/31913 - Monoolefin polymer
Y10T428/259 - Silicic material

C - CHEMISTRY C09 - DYES C09D - COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS
C09D133/14 - of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y10 - TECHNICAL SUBJECTS COVERED BY FORMER USPC Y10T - TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
Y10T428/31797 - Next to addition polymer from unsaturated monomers

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DOE Contract Number:: FC36-08GO18027

Resource Type:: Patent

Resource Relation:: Patent File Date: 2013 Mar 14

Country of Publication:: United States

Language:: English

Citation Formats


                    Clear, Susannah C., Padiyath, Raghunath, Lachmansingh, Garry W., Strobel, Mark A., Mackey, Sonja S., and Jing, Naiyong. Polymethylmethacrylate based hardcoat composition and coated article.  United States: N. p., 2018. 
        Web.

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                    Clear, Susannah C., Padiyath, Raghunath, Lachmansingh, Garry W., Strobel, Mark A., Mackey, Sonja S., & Jing, Naiyong. Polymethylmethacrylate based hardcoat composition and coated article.  United States.

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                    Clear, Susannah C., Padiyath, Raghunath, Lachmansingh, Garry W., Strobel, Mark A., Mackey, Sonja S., and Jing, Naiyong. Tue .  
        "Polymethylmethacrylate based hardcoat composition and coated article".  United States.  https://www.osti.gov/servlets/purl/1480291.

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@article{osti_1480291,

  title        = {Polymethylmethacrylate based hardcoat composition and coated article},

  author       = {Clear, Susannah C. and Padiyath, Raghunath and Lachmansingh, Garry W. and Strobel, Mark A. and Mackey, Sonja S. and Jing, Naiyong},

  abstractNote = {A coating composition is disclosed. The coating composition includes a poly(methyl methacrylate) polymer or copolymer having a weight average molecular weight of at least 50,000 grams per mole; monomer comprising at least one of an alkylene diacrylate, alkylene dimethacrylate, cycloalkylene diacrylate, or cycloalkylenedimethacrylate, wherein the at least one of an alkylene diacrylate, alkylene dimethacrylate, cycloalkylene diacrylate, or cycloalkylenedimethacrylate provides at least 80 percent by weight of the monomer; and a stabilizer against ultraviolet light. An article including a coating on a surface of a substrate and a method of making the article are also disclosed. The coating on the surface of the substrate is obtained by curing the disclosed coating composition.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2018},

  month        = {9}

}

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patent-application, May 2007

Hasskerl, Thomas; Becker, Patrick; Neeb, Rolf
US Patent Application 10/578568; 20070098884
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220070098884%22.PGNR.&OS=DN/20070098884&RS=DN/20070098884

Uv Hardening Glass Printing Ink And Uv Hardening Glass Printing Lacquer And Method For Printing A Glass Substrate
patent-application, September 2007

Lehmann, Saskia; Schaefer, Wolfgang
US Patent Application 10/576706; 20070213427
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220070213427%22.PGNR.&OS=DN/20070213427&RS=DN/20070213427

UV-curing protective layer for thermo-plastic substrates
patent-application, October 2007

Buckel, Frank; Maleika, Robert; Koehler, Walter
US Patent Application 11/732437; 20070237967
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220070237967%22.PGNR.&OS=DN/20070237967&RS=DN/20070237967

Laminate improving slippage of hardcoat layer
patent-application, October 2007

Hashimoto, Hiroyuki
US Patent Application 11/806046; 20070238845
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220070238845%22.PGNR.&OS=DN/20070238845&RS=DN/20070238845

Topcoat layers for phosphor or scintillator screens or panels
patent-application, January 2008

Williamson, Alexander; Tioni, Estevan; Heylen, Kristof
US Patent Application 11/811988; 20080026334
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220080026334%22.PGNR.&OS=DN/20080026334&RS=DN/20080026334

Hydrophilic Hard Coat Films
patent-application, January 2009

Hildenbrand, Karlheinz; Capellen, Peter; Koch, Eberhard
US Patent Application 12/171585; 20090017306
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220090017306%22.PGNR.&OS=DN/20090017306&RS=DN/20090017306

Exterior window film
patent-application, July 2009

Enniss, James P.; Pickett, Scott
US Patent Application 12/008606; 20090181242
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220090181242%22.PGNR.&OS=DN/20090181242&RS=DN/20090181242

Protective Overcoat of Photoreceptor Having a Charge Transport Compound
patent-application, August 2009

Coggan, Jennifer A.; Hu, Nan-Xing; Heuft, Matthew A.
US Patent Application 12/037567; 20090214969
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220090214969%22.PGNR.&OS=DN/20090214969&RS=DN/20090214969

Solar Concentrating Mirror
patent-application, November 2009

Hebrink, Timothy J.; Anderson, Tracy L.; Clear, Susannah C.
US Patent Application 12/466034; 20090283144
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220090283144%22.PGNR.&OS=DN/20090283144&RS=DN/20090283144

Coating Compositions Containing Polytrimethylene Ether Diol
patent-application, March 2011

Yokoyama, Ayumu; Sormani, Patricia Mary Ellen; Ma, Sheau-Hwa
US Patent Application 12/937429; 20110052919
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220110052919%22.PGNR.&OS=DN/20110052919&RS=DN/20110052919

Anti-Reflection/Anti-Fog Coatings
patent-application, December 2011

Hildenbrand, Karlheinz; Capellen, Peter; Bruder, Friedrich-Kark
US Patent Application 13/148975; 20110318567
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220110318567%22.PGNR.&OS=DN/20110318567&RS=DN/20110318567

Broadband Reflectors, Concentrated Solar Power Systems, And Methods Of Using The Same
patent-application, January 2012

Hebrink, Timothy J.; Clear, Susannah C.; Gilbert, Laurence R.
US Patent Application 13/142910; 20120011850
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220120011850%22.PGNR.&OS=DN/20120011850&RS=DN/20120011850

Reactive Mixture for Coating Molded Objects by Means of Reaction Injection Molding and Coated Molded Object
patent-application, January 2013

Schultes, Klaus; Goldacker, Thorsten; Koralewski, Klaus
US Patent Application 13/546051; 20130001825
URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220130001825%22.PGNR.&OS=DN/20130001825&RS=DN/20130001825

Photooxidative degradation of acrylic and methacrylic polymers
journal, March 2000

Chiantore, O.; Trossarelli, L.; Lazzari, M.
Polymer, Vol. 41, Issue 5, p. 1657-1668
https://doi.org/10.1016/S0032-3861(99)00349-3

Photo-oxidative stability of paraloid acrylic protective polymers
journal, January 2001

Chiantore, O.; Lazzari, M.
Polymer, Vol. 42, Issue 1, p. 17-27
https://doi.org/10.1016/S0032-3861(00)00327-X

Thermal-ageing of paraloid acrylic protective polymers
journal, August 2000

Lazzari, M.; Chiantore, O.
Polymer, Vol. 41, Issue 17, p. 6447-6455
https://doi.org/10.1016/S0032-3861(99)00877-0

Semi-interpenetrating polymer networks synthesis by photocrosslinking of acrylic monomers in a polymer matrix
journal, September 1993

Moussa, K.; Decker, C.
Journal of Polymer Science Part A: Polymer Chemistry, Vol. 31, Issue 10, p. 2633-2642
https://doi.org/10.1002/pola.1993.080311024

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Title: Polymethylmethacrylate based hardcoat composition and coated article

Abstract

Citation Formats

Solventless, ultraviolet radiation-curable silicone coating compositions patent, December 1984

Polysiloxane-grafted copolymer release coating sheets and adhesive tapes patent, March 1988

Xeroprinting with photopolymer master patent, March 1988

Radiation curable coating composition based on a silica/vinyl-functional silanol dispersion patent, April 1989

Low temperature processing transfer printing ink patent, August 1989

UV-stabilized coatings patent, September 1989

Radiation-curable coating for thermoplastic substrates patent, February 1990

Abrasion resistant radiation curable coating for polycarbonate article patent, September 1990

Multifunctional acrylate based abrasion resistant coating composition patent, December 1991

UV curable coating compositions, abrasion resistant UV stabilized thermoplastic composites and method patent, November 1992

Substrates having an abrasion-resistant coating formed thereon patent, February 1993

Abrasion-resistant coating compositions with improved weatherability patent, May 1993

Abrasion and water-resistant radiation curable coatings patent, November 1993

UV curable abrasion-resistant coatings with improved weatherability patent, June 1994

Method of producing a protective finish on a substrate patent, March 1995

Curable resin sols and fiber-reinforced composites derived therefrom patent, July 1997

Retroreflective sheeting having an abrasion resistant ceramer coating patent, October 1997

Process for the preparation of antiscratch and antiabrasion shaped articles based on acrylic polymers patent, December 1997

Transparent plastic pane containing a copolymer of methylmethacrylate and polyfunctional acrylates patent, December 1997

Radiation curable hardcoat compositions patent, January 1998

Radiation curable compositions having improved moisture resistance patent, September 1998

Acrylate polymer coated sheet materials and method of production thereof patent, April 2001

Ceramer compositions and antistatic abrasion resistant ceramers made therefrom patent, October 2001

Silico-acrylic compositions, method of preparation and application to the obtaining of coatings resistant to abrasion and scratching patent, January 2002

Polymerizable composition and optical articles using the same patent, October 2002

UV-curable compositions and method of use thereof in microelectronics patent, January 2004

Coating material that can be cured thermally or by actinic radiation, and its use patent, April 2004

UV curable paint compositions and method of making and applying same patent, June 2005

Light-curable resin composition having antistatic property patent, March 2006

Smudge resistant nanocomposite hardcoats and methods for making same patent, September 2006

Primer composition, coating method, and coated article patent, January 2007

Laminate improving slippage of hardcoat layer patent, July 2007

Methods, systems, and polymer substances relating to consideration of H2O levels present within an atmospheric-pressure nitrogen dielectric-barrier discharge patent, October 2008

Compositions for protective films for optical discs patent, June 2010

Composition for organic polymer gate insulating layer and organic thin film transistor using the same patent, June 2010

Branched polydiorganosiloxane polyamide copolymers patent, March 2011

Weather resistant, ink jettable, radiation curable, fluid compositions particularly suitable for outdoor applications patent, May 2011

Protective coating compositions and devices patent, July 2012

Glass printing ink or lacquer of epoxy resin, other resin and photoinitiator patent, August 2013

UV Curable Resin Composition for Coating patent-application, July 2001

Adhesive articles including a nanoparticle primer and methods for preparing same patent-application, March 2005

Anti-reflective optical film for display devices patent-application, May 2005

Radiation-curable coatings for wood substrates from multifunctional acrylate oligomers patent-application, November 2005

Scratch-resistant rear projection screen and method for producing the same patent-application, September 2006

Method for producing an antistatically coated molded body patent-application, May 2007

Uv Hardening Glass Printing Ink And Uv Hardening Glass Printing Lacquer And Method For Printing A Glass Substrate patent-application, September 2007

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Thermal-ageing of paraloid acrylic protective polymers journal, August 2000

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Solventless, ultraviolet radiation-curable silicone coating compositions
patent, December 1984

Polysiloxane-grafted copolymer release coating sheets and adhesive tapes
patent, March 1988

Xeroprinting with photopolymer master
patent, March 1988

Radiation curable coating composition based on a silica/vinyl-functional silanol dispersion
patent, April 1989

Low temperature processing transfer printing ink
patent, August 1989

UV-stabilized coatings
patent, September 1989

Radiation-curable coating for thermoplastic substrates
patent, February 1990

Abrasion resistant radiation curable coating for polycarbonate article
patent, September 1990

Multifunctional acrylate based abrasion resistant coating composition
patent, December 1991

UV curable coating compositions, abrasion resistant UV stabilized thermoplastic composites and method
patent, November 1992

Substrates having an abrasion-resistant coating formed thereon
patent, February 1993

Abrasion-resistant coating compositions with improved weatherability
patent, May 1993

Abrasion and water-resistant radiation curable coatings
patent, November 1993

UV curable abrasion-resistant coatings with improved weatherability
patent, June 1994

Method of producing a protective finish on a substrate
patent, March 1995

Curable resin sols and fiber-reinforced composites derived therefrom
patent, July 1997

Retroreflective sheeting having an abrasion resistant ceramer coating
patent, October 1997

Process for the preparation of antiscratch and antiabrasion shaped articles based on acrylic polymers
patent, December 1997

Transparent plastic pane containing a copolymer of methylmethacrylate and polyfunctional acrylates
patent, December 1997

Radiation curable hardcoat compositions
patent, January 1998

Radiation curable compositions having improved moisture resistance
patent, September 1998

Acrylate polymer coated sheet materials and method of production thereof
patent, April 2001

Ceramer compositions and antistatic abrasion resistant ceramers made therefrom
patent, October 2001

Silico-acrylic compositions, method of preparation and application to the obtaining of coatings resistant to abrasion and scratching
patent, January 2002

Polymerizable composition and optical articles using the same
patent, October 2002

UV-curable compositions and method of use thereof in microelectronics
patent, January 2004

Coating material that can be cured thermally or by actinic radiation, and its use
patent, April 2004

UV curable paint compositions and method of making and applying same
patent, June 2005

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patent, March 2006

Smudge resistant nanocomposite hardcoats and methods for making same
patent, September 2006

Primer composition, coating method, and coated article
patent, January 2007

Laminate improving slippage of hardcoat layer
patent, July 2007

Methods, systems, and polymer substances relating to consideration of H₂O levels present within an atmospheric-pressure nitrogen dielectric-barrier discharge
patent, October 2008

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patent, June 2010

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patent, June 2010

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patent, March 2011

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patent, May 2011

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patent, July 2012

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patent, August 2013

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patent-application, July 2001

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patent-application, March 2005

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patent-application, May 2005

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patent-application, November 2005

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patent-application, September 2006

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patent-application, May 2007

Uv Hardening Glass Printing Ink And Uv Hardening Glass Printing Lacquer And Method For Printing A Glass Substrate
patent-application, September 2007

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patent-application, October 2007

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patent-application, October 2007

Topcoat layers for phosphor or scintillator screens or panels
patent-application, January 2008

Hydrophilic Hard Coat Films
patent-application, January 2009

Exterior window film
patent-application, July 2009

Protective Overcoat of Photoreceptor Having a Charge Transport Compound
patent-application, August 2009

Solar Concentrating Mirror
patent-application, November 2009

Coating Compositions Containing Polytrimethylene Ether Diol
patent-application, March 2011

Anti-Reflection/Anti-Fog Coatings
patent-application, December 2011

Broadband Reflectors, Concentrated Solar Power Systems, And Methods Of Using The Same
patent-application, January 2012

Reactive Mixture for Coating Molded Objects by Means of Reaction Injection Molding and Coated Molded Object
patent-application, January 2013

Photooxidative degradation of acrylic and methacrylic polymers
journal, March 2000

Photo-oxidative stability of paraloid acrylic protective polymers
journal, January 2001

Thermal-ageing of paraloid acrylic protective polymers
journal, August 2000

Semi-interpenetrating polymer networks synthesis by photocrosslinking of acrylic monomers in a polymer matrix
journal, September 1993