Source: http://www.google.com/patents/US8158191?dq=6377161
Timestamp: 2014-12-20 21:09:47
Document Index: 91103016

Matched Legal Cases: ['Application No. 06749041', 'Application No. 200702687', 'application No. 2005295925', 'Application No. 200580042106', 'Application No. 06749041', 'Application No. 06', 'Application No. 2007', 'Application No. 200702687']

Patent US8158191 - Coating compositions, articles, and methods of coating articles - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inAdvanced Patent SearchPatentsProcesses for tinting a transparent, abrasion-resistant coating that is coated on at least one surface of a substrate are provided. The processes include coating the substrate with a transparent, tintable, abrasion-resistant coating composition, curing the coating composition on the substrate, and tinting...http://www.google.com/patents/US8158191?utm_source=gb-gplus-sharePatent US8158191 - Coating compositions, articles, and methods of coating articlesAdvanced Patent SearchPublication numberUS8158191 B2Publication typeGrantApplication numberUS 11/782,692Publication dateApr 17, 2012Filing dateJul 25, 2007Priority dateOct 12, 2004Also published asCA2583476A1, CN101072812A, EP1814930A2, EP1814930A4, US7265179, US8153196, US8153197, US20070104968, US20080014339, US20080145547, US20100310876, US20120049401, WO2006044340A2, WO2006044340A3Publication number11782692, 782692, US 8158191 B2, US 8158191B2, US-B2-8158191, US8158191 B2, US8158191B2InventorsAndreas Schneider, Ren-Zhi Jim, Mark SollbergerOriginal AssigneeSdc Coatings, Inc.Export CitationBiBTeX, EndNote, RefManPatent Citations (49), Non-Patent Citations (32), Classifications (22), Legal Events (3) External Links: USPTO, USPTO Assignment, EspacenetCoating compositions, articles, and methods of coating articlesUS 8158191 B2Abstract Processes for tinting a transparent, abrasion-resistant coating that is coated on at least one surface of a substrate are provided. The processes include coating the substrate with a transparent, tintable, abrasion-resistant coating composition, curing the coating composition on the substrate, and tinting the cured coating by immersing the cured coating in a dye bath for a period of time.
CROSS REFERENCE TO RELATED APPLICATIONS This application is divisional of and claims priority to and any other benefit of U.S. Non-provisional application Ser. No. 11/278,363, filed Mar. 31, 2006, which is a continuation-in-part of and claims priority to and any other benefit of PCT Application No. PCT/US2005/036458, filed Oct. 12, 2005, which claims priority to and any other benefit of U.S. Provisional Application Ser. No. 60/618,014, filed Oct. 12, 2004, the entirety of all which are incorporated by reference herein. Furthermore, U.S. Non-provisional application Ser. No. 11/278,363 is related to PCT Application No. PCT/US2006/011957 entitled �Coating Compositions, Articles, and Methods of Coating Articles�, which was filed Mar. 31, 2006.
FIELD OF THE INVENTION The present invention relates to coating compositions, articles, and methods of coating articles. More particularly, the present invention relates to stable coating compositions that provide abrasion resistant formable coatings when cured on a substrate. Additionally, the present invention relates to stable coating compositions that provide abrasion resistant, environmentally resistant, tintable coatings when cured on a substrate.
SUMMARY OF THE INVENTION In accordance with embodiments of the present invention, compositions which, when applied to a substrate and cured, provide an abrasion resistant formable coating on the substrate are provided. The compositions can comprise an aqueous-organic solvent mixture having hydrolysis products and partial condensates of at least one of an epoxy functional silane and a diol functional organopolysiloxane and at least one multifunctional crosslinker, wherein the multifunctional crosslinker comprises a silylated multifunctional anhydride, and wherein the at least one of the epoxy functional silane and the diol functional organopolysiloxane is present in a molar ratio to the multifunctional crosslinker from about 10:1 to about 1:10; and an amount of water sufficient to hydrolyze the epoxy functional silane, the diol functional organopolysiloxane, and the multifunctional crosslinker.
Example 4 Coating Composition and Primer 17.0 grams of DI water were added dropwise to a stirring solution of 45.0 grains of A-187, 29.0 grams of GF20, and 280.0 grams of isopropanol. The mixture was stirred at room temperature overnight. 0.37 grams of a solution of PA-57, 10 weight percent in PM glycol ether, were added. The composition was left to stir for an additional 20 minutes after the addition of the PA-57 to insure mixing.
Example 7 Coating Composition and Primer 14.3 grams of DI water were added dropwise to a stirring solution of 30.0 grains of A-187, 38.6 grams of GF20, and 300.0 grams of PM glycol ether (PMOH) solvent. The mixture was stirred at room temperature for three days. 0.38 grams of a solution of PA-57, 10 weight percent in PMOH, were added. The composition was left to stir for an additional 20 minutes after the addition of the PA-57 to insure mixing.
Example 9 Coating Composition and Primer 15.8 grams of DI water were added dropwise to a stirring solution of 47.2 grams of A-187, 20.3 grams of GF20, and 300.0 grains of PM glycol ether (PMOH). The mixture was stirred at room temperature for three days. 0.38 grams of a solution of PA-57, 10 weight percent in PMOH, were added. The composition was left to stir for an additional 20 minutes after the addition of the PA-57 to insure mixing.
Example 13 Coating Composition and Primer 4.0 grams of DI water were added dropwise to a stirring suspension of 15.0 grams of A-187, 1.4 grams of succinic anhydride crosslinker, and 70.0 grams of isopropanol. The mixture was stirred at room temperature overnight. 0.10 grains of a solution of PA-57, 10 weight percent in PMOH, were added. The composition was left to stir for an additional 20 minutes after the addition of the PA-57 to insure mixing.
Example 17 Coating Composition and Primer A mixture of 15.0 grams of HS2926, 0.7 grams of succinic anhydride, and 30.0 grams of isopropanol was stirred at room temperature overnight. 0.05 grams of a solution of PA-57, 10 weight percent in PMOH, were added. The composition was left to stir for an additional 20 minutes after the addition of the PA-57 to insure mixing. This coating composition was applied by flow coating to a PR-1180 primed �″ thick polycarbonate plaque. After air-drying for 30 minutes, the coating was cured for 2 hours at 130� C. Haze gain results from a Taller test using CS-10F wheels were: 26.0% haze at 25 revolutions. Formability of the coating was evaluated on a cylindrical mandrel and no crack was observed at 3″ radius.
Example 21 Anti-Fog Coating Composition and Primer 1.91 grains of DI water were added dropwise to a stirring solution of 4.0 grams of A-187, 5.15 grams of GF20, and 40 grams of PM glycol ether. The mixture was stirred at room temperature overnight. 0.74 grains of surfactant sodium dioctyl sulfosuccinate in mixture of ethanol and water (OT-75) Van Waters & Rogers Inc., Kirkland, Wash.) (75% solid) was added. The composition was left to stir for two hours at room temperature and then aged at a 100 F warm room for 3 weeks before coating application.
Example 24 Coating and Weatherable Primer A weatherable primer was prepared by mixing a Poly(oxy-1,2-ethanediyl), .alpha.-[3-[3-(2H-benzotriazo(-2-yl)-5-(1,1-dimethylethyl)-4-hydroxyphenyl)-1-oxopropyl]-.omega.-[3-[3 [(2H-benzotriazol-2-yl)-5-(1,1-dimethylethyl)-4-hydroxyphenyl]-1-oxopropoxy], 30-45% by wt. and Poly(oxy-1,2-ethanediyl), .alpha.-[3-[3-(2H-benzotriazo(-2-yl)-5-(1,1-dimethylethyl)-4-hydroxyphenyl)-1-oxopropyl]-.omega.-hydroxy-, 40-55% by wt. (Tinuvin 1130, Ciba Specialty Chemicals Corporation, Tarrytown, N.Y.) into a commercially available PR1180 primer. Thus, 6.42 grams of Tinuvin1130 was added to 150 grams of PR1180. The resulting composition was left to stir for four hours before coating application.
Example 26 Tintable Coating and Tinting on Nylon Lenses 26.4 grams of DI water were added dropwise to a stirring solution of 52.7 grams of A-187, 68.0 grams of GF20, and 147 grains of isopropanol. The mixture was stirred at room temperature overnight. 63 grams of PM glycol ether and 0.53 grams of a solution of PA-57, 10 weight percent in PM glycol ether, were added. The composition was left to stir for an additional 20 minutes after the addition to insure mixing.
Example 27 Tintable Coating Having a Blocked Isocyanate on Nylon/CR-39 Lenses 5.93 grams of DI water were added dropwise to a stirring solution of 11.9 grams of A-187, 15.2 grams of GF20, and 32.5 grams of isopropanol. The mixture was stirred at room temperature overnight. 19 grams of PM glycol ether, 2.61 grams of BL 3175A, and 0.12 grams of a solution of PA-57, 10 weight percent in PM glycol ether, were added. The composition was left to stir for an additional 20 minutes after the addition to insure mixing.
Example 28 Tintable Coating Having a Blocked Isocyanate and Tinting on Nylon Lenses 26.4 grams of DI water were added dropwise to a stirring solution of 52.7 grams of A-187, 68.0 grams of GF20, and 73.5 grams of isopropanol. The mixture was stirred at room temperature overnight. 157 grams of PM glycol ether, 11.8 grams of BL, 3175A, and 0.53 grains of a solution of PA-57, 10 weight percent in PM glycol ether, were added. The composition was left to stir for an additional 20 minutes after the addition to insure mixing.
Example 29 Tintable Coating Having a Blocked Isocyanate on Nylon Lens 260 grams of DI water were added dropwise to a stirring solution of 211 grams of A-187, 272 grams of GF20, and 764 grams of PM glycol ether. The mixture was stirred at room temperature overnight. 47.2 grains of BL, 3175A and 2.12 grains of a solution of PA-57, 10 weight percent in PM glycol ether, were added. The composition was left to stir for an additional 20 minutes after the addition to insure mixing.
Example 30 Tintable Coating Having a Blocked Isocyanate�Nylon/Trivex/ADC/MR� 8 Lens 87.0 grams of DI water were added dropwise to a stirring solution of 52.7 grains of A-187, 68.0 grams of GF20, and 87.0 grams of PM glycol ether. The mixture was stirred at room temperature overnight. 78.0 grams of PM glycol ether, 11.8 grams of BL 3175A, and 0.53 grams of a solution of PA-57, 10 weight percent in PM glycol ether, were added. The composition was left to stir for an additional 20 minutes after the addition to insure mixing.
Example 31 Tintable Coating Having a Blocked Isocyanate 87.0 grams of DI water were added dropwise to a stirring solution of 63.2 grams of A-187, 61.2 grams of GF20, and 87.0 grams of PM glycol ether. The mixture was stirred at room temperature overnight. 78.0 grams of PM glycol ether, 11.8 grams of BL 3175A, and 0.60 grams of a solution of PA-57, 10 weight percent in PM glycol ether, were added. The composition was left to stir for an additional 20 minutes after the addition to insure mixing.
Example 32 Tintable Coating Composition Having a Blocked Isocyanate 87.0 grams of DI water were added dropwise to a stirring solution of 73.7 grams of A-187, 47.6 grams of GF20, and 87.0 grams of PM glycol ether. The mixture was stirred at room temperature overnight. 78.0 grams of PM glycol ether, 11.8 grains of BL, 3175A, and 0.60 grams of a solution of PA-57, 10 weight percent in PM glycol ether, were added. The composition was left to stir for an additional 20 minutes after the addition to insure mixing.
Example 33 Primer/Tintable Coating The coating composition of Example 30 was applied by dip-coating at a withdrawal rate of 12 ipm to a PR-1135 primed polycarbonate lens, which was dip-coated at withdrawal rate of 5 ipm. After air-drying for 30 minutes, the coating composition was cured for 2 hours at 112� C. to provide a cured film having a Bayer number of 2.24, excellent steel wool abrasion resistance, and around 6.5% light transmittance after 30 min tinting in accordance with the procedure in Example 26. The weatherability of the coatings was evaluated by QUV method B in accordance with the procedure in the specification. The non-tinted coating showed adhesion failure after 120 hours exposure. The tinted coating showed no adhesion failure or crack after 120 hours exposure. For the test method B, the QUV unit is set for repeating cycles of 4 hours UV-B exposure (0.8 W/m2/nm) with a panel temperature of 48� C. and 4 hours of condensation with a panel temperature of 50� C.
Example 34 Primer Having a Crosslinking Agent/Tintable Coating 6.0 grams of BI7986 was added to 400 grams of the primer PR-1135. The resulting composition was left to stir for one hour at room temperature. This composition was applied as a primer by dip-coating at a withdrawal rate of 5 ipm to a polycarbonate lens. The primer was air dried for 30 min before an application of a coating composition of Example 30. The Example 30 coating composition was applied by dip-coating at a withdrawal rate of 12 ipm. After air-drying for 30 minutes, the final coating composition was cured for 2 hours at 112� C. to provide a cured film having a Bayer number of 2.24, excellent steel wool abrasion resistance, and around 7.9% light transmittance after 30 min tinting in accordance with the procedure of Example 26. The weatherability of the coatings was evaluated by QUV method B in accordance with the procedure in the specification. The non-tinted coating showed adhesion failure after 120 hours exposure. The tinted coating showed no adhesion failure or crack after 120 hours exposure. For the test method B, the QUV unit is set for repeating cycles of 4 hours UV-B exposure (0.8 W/n2/nm) with a panel temperature of 48� C. and 4 hours of condensation with a panel temperature of 50� C.
Example 35 Primer Having a Crosslinking Agent/Tintable Coating 12.0 grams of BI7986 was added to 400 grams of the primer PR-1135. The resulting composition was left to stir for one hour at room temperature. This composition was applied as a primer by dip-coating at a withdrawal rate of 5 ipm to a polycarbonate lens. The primer was air dried for 30 min before an application of a topcoat of example 30. The Example 30 coating composition was applied by dip-coating at a withdrawal rate of 12 ipm. After air-drying for 30 minutes, the final coating composition was cured for 2 hours at 112� C. to provide a cured film having a Bayer number of 2.24, excellent steel wool abrasion resistance, and around 7.4% light transmittance after 30 min tinting in accordance with the procedure of Example 26. The weatherability of the coatings was evaluated by QUV method B in accordance with the procedure in the specification. The non-tinted coating showed adhesion failure after 120 hours exposure. The tinted coating showed no adhesion failure and crack after 120 hours exposure. For the test method B, the QUV unit is set for repeating cycles of 4 hours UV-B exposure (0.8 W/m2/ml) with a panel temperature of 48� C. and 4 hours of condensation with a panel temperature of 50� C.
Example 36 Primer Having a Crosslinking Agent/Tintable Coating The primer composition of example 35 was applied by dip-coating at a withdrawal rate of 5 ipm to a polycarbonate lens. The primer was air dried for 30 min before an application of a topcoat of example 32. The Example 32 coating composition was applied by dip-coating at a withdrawal rate of 12 ipm. After air-drying for 30 minutes, the final coating composition was cured for 2 hours at 112� C. to provide a cured film having a Bayer number of 2.15, excellent steel wool abrasion resistance, and around 20% light transmittance after 30 mill tinting in accordance with the procedure of Example 26. The weatherability of the coatings was evaluated by QUV method A in accordance with the procedure in the specification. Both of the tinted and non-tinted coatings showed no adhesion failure or crack after 160 hours exposure. For the test method A, the QUV unit is set for repeating cycles of 4 hours UV-A exposure (0.8 W/m2/nm) and 4 hours of condensation with a panel temperature of 55� C.
Example 37 Primer Having Crosslinking Agent/Tintable Coating 18.0 grams of B17986 was added to 400 grams of the primer PR-1135. The resulting composition was left to stir for one hour at room temperature. This composition was applied as a primer by dip-coating at a withdrawal rate of 5 ipm to a polycarbonate lens. The primer was air dried for 30 min before an application of a topcoat of Example 30. The Example 30 coating composition was applied by dip-coating at a withdrawal rate of 12 ipm. After air-drying for 30 minutes, the final coating composition was cured for 2 hours at 112� C. to provide a cured film having a Bayer number of 2.24, excellent steel wool abrasion resistance, and around 8.4% light transmittance after 30 min tinting in accordance with the procedure of Example 26. The weatherability of the coatings was evaluated by QUV method B in accordance with the procedure in the specification. The non-tinted coating showed adhesion failure after 120 hours exposure. The tinted coating showed no adhesion failure or crack after 120 hours exposure with no adhesion failure and crack. For the test method B, the QUV unit is set for repeating cycles of 4 hours UV-B exposure (0.8 W/m2/nm) with a panel temperature of 48� C. and 4 hours of condensation with a panel temperature of 50� C.
Example 38 Comparative Example Coating Having Blocked Isocyanate on Nylon Lens 87.0 grams of DI water were added dropwise to a stirring solution of 52.7 grams of A-187, 29.0 grams of itaconic acid, and 87.0 grams of PM glycol ether. The mixture was stirred at room temperature overnight. 78.0 grams of PM glycol ether, 11.8 grams of BL 3175A, and 0.53 grams of a solution of PA-57, 10 weight percent in PM glycol ether, were added. The composition was left to stir for an additional 20 minutes after the addition to insure mixing. This coating composition was applied by dip-coating to a Nylon lens at a withdrawal rate of 20 ipm. After air-drying for 30 minutes, the coating composition was cured for 2 hours at 112� C. A severe hazy film was obtained.
Example 39 Comparative Example Coating Having Blocked Isocyanate on Nylon Lens 87.0 grams of DI water were added dropwise to a stirring solution of 52.7 grams of A-187, 7.25 grams of itaconic acid, and 87.0 grams of PM glycol ether. The mixture was stirred at room temperature overnight. 78.0 grams of PM glycol ether, 11.8 grams of BL, 3175A, and 0.53 grams of a solution of PA-57, 10 weight percent in PM glycol ether, were added. The composition was left to stir for an additional 20 minutes after the addition to insure mixing. This coating composition was applied by dip-coating to a Nylon lens at a withdrawal rate of 20 ipm. After air-drying for 30 minutes, the coating composition was cured for 2 hours at 112� C. to provide a cured film having a thickness of about 2.5 microns, a Bayer number of 1.22, poor steel wool abrasion resistance, and 3.7% light transmittance after 30 min tinting.
Example 40 Comparative Example Coating Having Blocked Isocyanate on Nylon Lens 87.0 grams of DI water were added dropwise to a stirring solution of 52.7 grams of A-187, 22.3 grains of succinic anhydride, and 87.0 grams of PM glycol ether. The mixture was stirred at room temperature overnight. 78.0 grams of PM glycol ether, 11.8 grams of BL 3175A, and 0.53 grains of a solution of PA-57, 10 weight percent in PM glycol ether, were added. The composition was left to stir for an additional 20 minutes after the addition to insure mixing. This coating composition was applied by dip-coating to a Nylon lens at a withdrawal rate of 20 ipm. After air-drying for 30 minutes, the coating composition was cured for 2 hours at 112� C. A severe hazy film was obtained.
Example 41 Comparative Example Coating Having Blocked Isocyanate on Nylon Lens 87.0 grams of DI water were added dropwise to a stirring solution of 52.7 grams of A-187, 5.57 grams of succinic anhydride, and 87.0 grams of PM glycol ether. The mixture was stirred at room temperature overnight. 78.0 grams of PM glycol ether, 11.8 grams of BL, 3175A, and 0.53 grams of a solution of PA-57, 10 weight percent in PM glycol ether, were added. The composition was left to stir for an additional 20 minutes after the addition to insure mixing. This coating composition was applied by dip-coating to a Nylon lens at a withdrawal rate of 20 ipm. After air-drying for 30 minutes, the coating composition was cured for 2 hours at 112� C. to provide a cured film having a thickness of about 2.2 microns, a Bayer number of 0.56, poor steel wool abrasion resistance, and 3.2% light transmittance after 30 min tinting.
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No. 12/295,519 dated Sep. 29, 2010.27Supplementary European Search Report from EP Application No. EP 06 74 9041, dated Apr. 14, 2010.28Taber Industries, Jul. 2003: Important Notice Regarding TABER CS-10F Wheels, 3 pages.29Translation of Japanese Office Action for Japanese Patent Application No. 2007-536787, dated Aug. 26, 2011.30Written Opinion and Search Report issued by the Australian Patent Office for related Singapore Patent Application No. 200702687-5 dated Jul. 3, 2008.31Written Opinion from PCT/US05/36458, mailed Nov. 27, 2006.32Written Opinion from PCT/US06/11957, mailed Sep. 25, 2006.Classifications U.S. Classification427/162, 427/384International ClassificationB05D5/06Cooperative ClassificationC08G59/423, C09D183/04, C08G59/4085, C08G18/289, C08J2483/00, C08J7/047, C08G77/16, C09D183/06, C08G18/8061, C09D175/04European ClassificationC08G18/80H, C09D175/04, C08G18/28D8N, C08J7/04L, C09D183/06, C08G59/40B6, C08G59/42H, C09D183/04, C08G77/16Legal EventsDateCodeEventDescriptionJul 31, 2012CCCertificate of correctionJun 13, 2012ASAssignmentOwner name: SDC TECHNOLOGIES, INC., CALIFORNIAFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:SDC COATINGS, INC.;REEL/FRAME:028364/0478Effective date: 20120606Jul 25, 2007ASAssignmentOwner name: SDC COATINGS, INC., CALIFORNIAFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:SCHNEIDER, ANDREAS;JIM, REN-ZHI;SOLLBERGER, MARK;REEL/FRAME:019607/0055;SIGNING DATES FROM 20060501 TO 20060517Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:SCHNEIDER, ANDREAS;JIM, REN-ZHI;SOLLBERGER, MARK;SIGNINGDATES FROM 20060501 TO 20060517;REEL/FRAME:019607/0055RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services©2012 Google