CA2598046A1 - Photochromic coating compositions, methods of making coated articles and articles thereof - Google Patents

Photochromic coating compositions, methods of making coated articles and articles thereof Download PDF

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Publication number
CA2598046A1
CA2598046A1 CA 2598046 CA2598046A CA2598046A1 CA 2598046 A1 CA2598046 A1 CA 2598046A1 CA 2598046 CA2598046 CA 2598046 CA 2598046 A CA2598046 A CA 2598046A CA 2598046 A1 CA2598046 A1 CA 2598046A1
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CA
Canada
Prior art keywords
polymer
coating composition
precursor materials
diisocyanate
ungelled
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
CA 2598046
Other languages
French (fr)
Other versions
CA2598046C (en
Inventor
Jeanine A. Conklin
Eric M. King
Kevin J. Stewart
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.)
Transitions Optical Inc
Original Assignee
Transitions Opitical, Inc.
Jeanine A. Conklin
Eric M. King
Kevin J. Stewart
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 Transitions Opitical, Inc., Jeanine A. Conklin, Eric M. King, Kevin J. Stewart filed Critical Transitions Opitical, Inc.
Priority to CA 2686420 priority Critical patent/CA2686420A1/en
Publication of CA2598046A1 publication Critical patent/CA2598046A1/en
Application granted granted Critical
Publication of CA2598046C publication Critical patent/CA2598046C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
    • C09K9/02—Organic tenebrescent materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • 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

Abstract

Described are ungelled coating compositions of photochromic material, precursor materials for a first polymer polymerizable by free-radical initiated polymerization and precursor materials for a second or additional polymer(s) different from the first polymer. When the second polymer is selected from polyurethane, poly(urea-urethane) and mixtures thereof, the precursor materials include at least one blocked polyisocyanate. Also described are methods of making photochromic articles using the ungelled coating compositions and the photochromic articles produced using these methods.

Claims (28)

1. An ungelled coating composition comprising a photochromic material, precursor materials for a first polymer polymerizable by free-radical initiated polymerization and precursor materials for a second polymer selected from polyurethane, poly(urea-urethane) and mixtures thereof, the precursor materials for said second polymer comprising at least one blocked polyisocyanate.
2. The ungelled coating composition of claim 1 wherein said precursor materials for the first polymer comprise ethylenically unsaturated groups.
3. The ungelled coating composition of claim 2 wherein said unsaturated groups are selected from allylic groups, methacrylic groups, acrylic groups, vinyl groups and mixtures thereof.
4. The ungelled coating composition of claim 1 wherein said blocked polyisocyanate is essentially free of unblocked isocyanate groups.
5. The ungelled coating composition of claim 4 wherein said blocked polyisocyanate is selected from: aliphatic polyisocyanates; aromatic polyisocyanates; cycloaliphatic polyisocyanates; heterocyclic polyisocyanates;

derivatives thereof and mixtures thereof.
6. The ungelled coating composition of claim 5 wherein said aliphatic polyisocyanates are selected from: tetramethylene-1,4-diisocyanate;
hexamethylene-1,6-diisocyanate; 2,2,4-trimethyl hexane-1,6-diisocyanate;
lysine methyl ester diisocyanate; bis (isocyanato ethyl)fumarate; ethylene diisocyanate;
dodecane-1,12-diisocyanate; derivatives thereof and mixtures thereof; said aromatic polyisocyanates are selected from: toluene-2,4-diisocyanate; toluene-2,6-diisocyanate; diphenyl methane -4,4'-diisocyanate; diphenyl methane-2,4'-diisocyanate; para-phenylene diisocyanate; biphenyl diisocyanate; 3,3'-dimethyl-4,4'-diphenylene diisocyanate; derivatives thereof and mixtures thereof; said cycloaliphatic polyisocyanates are selected from: isophorone diisocyanate;
cyclobutane-1,3-diisocyanate; cyclohexane-1-3-diisocyanate; cyclohexane-1,4-diisocyanate; methyl cyclohexyl diisocyanate; perhydrodiphenylmethane-2,4'-diisocyanate; perhydrodiphenylmethane-4,4'-diisocyanate, derivatives thereof and mixtures thereof.
7. The ungelled coating composition of claim 6 wherein the blocking agent of said blocked polyisocyanate is volatile alcohol selected from: methanol and diisopropyl amine; epsilon-caprolactam; azole-containing material selected from 1,2,4-triazole and 3,5-dimethyl pyrazole; methyl ethyl ketoxime; and mixtures thereof.
8. The ungelled coating composition of claim 1 wherein when the second polymer is polyurethane, the precursor materials further comprise a polyol and when the second polymer is poly(urea-urethane), the precursor materials further comprise a polyamine and a polyol.
9. The ungelled coating composition of claim 8 wherein the polyamine comprises an aliphatic polyamine, aromatic polyamine and mixtures thereof.
10. The ungelled coating composition of claim 9 wherein each of the polyol precursor materials for the second polymer are independently selected from:
low molecular weight polyols; polyester polyols; polyether polyols; amide-containing polyols; polyacrylic polyols; epoxy polyols; polyhydric polyvinyl alcohols;
polycarbonate polyols; urethane polyols; and mixtures thereof.
11. The ungelled coating composition of claim 10 wherein each of the precursor materials for the second polymer independently further comprise a catalyst selected from: tin octylate; dibutyltin diacetate; dibutyltin dilaurate; dibutyltin mercaptide;
dibutyltin dimaleate; dimethyltin diacetate; dimethyltin dilaurate;
dimethyltin mercaptide; dimethyltin dimaleate; triphenyltin acetate; triphenyltin hydroxide; 1,4-diazabicyclo[2.2.2]octane; triethylamine; bismuth carboxylate and mixtures thereof.
12. The ungelled coating composition of claim 1 wherein the photochromic material is selected from inorganic photochromic materials, organic photochromic materials and mixtures thereof.
13. The ungelled coating composition of claim 12 wherein said organic photochromic material is selected from pyrans, oxazines, fulgides, fulgimides, diarylethenes and mixtures thereof.
14. The ungelled coating composition of claim 13 wherein said organic photochromic material is adapted to polymerize with the precursor materials for the first polymer and/or with the precursor materials for the second polymer.
15. An ungelled coating composition comprising a photochromic material, precursor materials for a first polymer polymerizable by free-radical initiated polymerization and precursor materials for one or more additional polymer(s) different from the first polymer, said ungelled coating composition being substantially free of polyurethanes and/or poly(urea-urethanes).
16. The ungelled coating composition of claim 15 wherein said ungelled coating composition is essentially free of polyisocyanates.
17. The ungelled coating composition of claim 16 wherein the additional polymer(s) is selected from: polyepoxides; polyoxetanes; aminoplast-containing polymers, tris(alkoxycarbonylamino)triazine-containing polymers, polyanhydride-containing polymers; polyacrylamide-containing polymers; polyethers;
(meth)acrylic addition interpolymers; organopolysiloxanes; and mixtures thereof.
18. A method of making a photochromic coated article comprising:
a) obtaining a substrate;
b) connecting to a surface of said substrate an at least partial coating of an ungelled coating composition comprising a photochromic material, precursor materials for a first polymer polymerizable by free-radical initiated polymerization and precursor materials for a second polymer selected from polyurethane, poly(urea-urethane) and mixtures thereof, said precursors for the second polymer comprising at least one blocked polyisocyanate; and c) at least partially curing the coating of said ungelled coating composition.
19. The method of claim 18 wherein the ungelled coating composition of (b) comprises a photochromic material, precursor materials for a first polymer polymerizable by free-radical initiated polymerization and precursor materials for one or more additional polymer(s) different from the first polymer, said ungelled coating composition being substantially free of polyurethanes and/or poly(urea-urethanes).
20. The method of claim 18 wherein said substrate is a material selected from:

glass; ceramic; and polymeric organic material.
21. The method of claim 20 wherein the substrate is an optical element.
22. The method of claim 18 wherein the at least partial curing of the coating of said ungelled coating composition is carried out such that an at least partial cure of the precursor materials for the second polymer is commenced prior to completion of cure of precursor materials for the first polymer.
23. The method of claim 19 wherein the at least partial curing of the coating of said ungelled coating composition is carried out such that an at least partial cure of the precursor materials for said one or more additional polymer(s) is commenced prior to completion of cure of precursor materials for the first polymer.
24. A photochromic coated article produced by the method of claim 18.
25. A method of making a photochromic coated lens comprising:

a) obtaining a lens coating apparatus;
b) obtaining a lens;
c) introducing said lens to the lens coating apparatus;
d) connecting to a surface of said lens an at least partial coating of an ungelled coating composition comprising a photochromic material, precursor materials for a first polymer polymerizable by free-radical initiated polymerization and precursor materials for a second polymer selected from polyurethane, poly(urea-urethane) and mixtures thereof, said precursor materials for the second polymer comprising at least one blocked polyisocyanate; and e) at least partially curing the coating of said ungelled coating composition.
26. The method of claim 25 wherein the at least partial curing of the coating of said ungelled coating composition of (e) is carried out such that an at least partial cure of the precursor materials for the second polymer is commenced prior to completion of cure of precursor materials for the first polymer.
27. The method of claim 26 wherein the at least partial curing of the precursor materials for the first polymer is by exposure to actinic radiation and/or thermal radiation to produce an at least partially tack free coated surface.
28. A photochromic coated lens produced by the method of claim 25.
CA 2598046 2004-10-29 2005-09-30 Photochromic coating compositions, methods of making coated articles and articles thereof Expired - Fee Related CA2598046C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA 2686420 CA2686420A1 (en) 2004-10-29 2005-09-30 Photochromic coating compositions, methods of making coated articles and articles thereof

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US62361204P 2004-10-29 2004-10-29
US60/623,612 2004-10-29
US11/231,867 US20060093844A1 (en) 2004-10-29 2005-09-22 Photochromic coating compositions, methods of making coated articles and articles thereof
US11/231,867 2005-09-22
PCT/US2005/035577 WO2006049786A1 (en) 2004-10-29 2005-09-30 Photochromic coating compositions, methods of making coated articles and articles thereof

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA 2686420 Division CA2686420A1 (en) 2004-10-29 2005-09-30 Photochromic coating compositions, methods of making coated articles and articles thereof

Publications (2)

Publication Number Publication Date
CA2598046A1 true CA2598046A1 (en) 2006-05-11
CA2598046C CA2598046C (en) 2010-12-21

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Family Applications (2)

Application Number Title Priority Date Filing Date
CA 2598046 Expired - Fee Related CA2598046C (en) 2004-10-29 2005-09-30 Photochromic coating compositions, methods of making coated articles and articles thereof
CA 2686420 Abandoned CA2686420A1 (en) 2004-10-29 2005-09-30 Photochromic coating compositions, methods of making coated articles and articles thereof

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA 2686420 Abandoned CA2686420A1 (en) 2004-10-29 2005-09-30 Photochromic coating compositions, methods of making coated articles and articles thereof

Country Status (5)

Country Link
US (1) US20060093844A1 (en)
EP (1) EP1844115A1 (en)
AU (1) AU2005301171B2 (en)
CA (2) CA2598046C (en)
WO (1) WO2006049786A1 (en)

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Also Published As

Publication number Publication date
WO2006049786A1 (en) 2006-05-11
US20060093844A1 (en) 2006-05-04
AU2005301171A1 (en) 2006-05-11
AU2005301171B2 (en) 2010-02-18
EP1844115A1 (en) 2007-10-17
CA2598046C (en) 2010-12-21
CA2686420A1 (en) 2006-05-11

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