EP0383074A2
Expired / Lapsed
EP
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Radiation-curable coating compositions that form transparent, abrasion-resistant tintable coatings
Assignee: GKN Aerospace Transparency Systems Inc
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Filing: 1990-01-25
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Granted: —
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Expires: 2010-01-25
Abstract
Abstract Radiation-curable coating compositions which form transparent, abrasion-resistant, tintable coatings upon curing by exposure to high intensity irradiation, such as ultraviolet light or electron beam irradiation. The coating composition comprises a combination of effective amounts of (a) colloidal silica, (b) the hydrolysis product of a silane compound having a polymerizable functional group such as acryloxy-functional silanes or glycidoxy-functional silanes or mixtures of both, (c) polyfunctional, polymerizable, non-acryloxy-functional ethers, (d) at least one radiation sensitive initiator and, preferably, (e) a monofunctional monomer. When the surface of a substrate coated with the cured coating composition is immersed in a colored dye bath for a sufficient period of time, the coating absorbs or transmits to the substrate a desired amount of dye.
Inventors
- 👤 William Clarence Perkins
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-02 21:15
CPC Classifications
C; C09; C09D; C09D183/00; C09D4/00
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
72 words
A radiation-curable coating composition which forms a transparent, abrasion-resistant, tintable coating upon curing, said coating comprising: a. an effective abrasion-resistant amount of colloidal silica; b. about 0.05 to about 5 parts by weight per each part colloidal silica of a hydrolysis product of a silane compound having a polymerizable functional group; c. an effective tintable amount of a polyfunctional, polymerizable non-acrylate-functional ether; and d. a catalytic amount of a radiation sensitive initiator.
Claim 2
Dependent Claim
72 words
A radiation-curable coating composition which forms a transparent, abrasion-resistant, tintable coating upon curing, said coating comprising: a. an effective abrasion-resistant amount of colloidal silica; b. about 0.05 to about 5 parts by weight per each part colloidal silica of a hydrolysis product of a silane compound having a polymerizable functional group; c. an effective tintable amount of a polyfunctional, polymerizable non-acrylate-functional ether; and d. a catalytic amount of a radiation sensitive initiator.
Claim 3
Dependent Claim
138 words
A coating composition as in claim 1 wherein said silane is selected from (i) acryloxy-functional silanes having a general formula: wherein R³ and R⁴ are the same or different monovalent hydrocarbon radicals, R⁵ is a divalent hydrocarbon radical having 2 to 3 carbon atoms, R⁶ is hydrogen or a monovalent hydrocarbon radical, b is an integer from 1 to 3, c is an integer from 0 to 2, and d is an integer equaling 4-b-c; or (ii) glycidoxy-functional silanes having a general formula: wherein R⁷ and R⁸ are the same or different monovalent hydrocarbon radicals, R⁹ is a divalent hydrocarbon radical having from 2 to 8 carbon atoms, e is an integer from 1 to 3, f is an integer from 0 to 2, and g is an integer equaling 4-e-f; or (iii) mixtures of (i) and (ii).
Claim 4
Dependent Claim
13 words
A coating composition as in claim 2 which additionally comprises a monofunctional monomer.
Claim 5
Dependent Claim
43 words
A coating composition as in claim 2 wherein said acryloxy-functional silane is selected from the group consisting of 3-methacryloxypropyltrimethoxysilane; 3-acryloxypropyltrimethoxysilane; 2-methacryloxyethyltrimethoxysilane; 2-acryloxyethyltrimethoxysilane; 3-methacryloxypropyltriethoxysilane; 3-acryloxypropyltriethoxysilane; 2-methacryloxyethyltriethoxysilane; and 2-acryloxyethyltriethoxysilane; and said glycidoxy-functional silane is selected from the group consisting of 3-glycidoxypropyltrimethoxysilane; 2-glycidoxyethyltrimethoxysilane; 3-glycidoxypropyltriethoxysilane; and 2-glycidoxyethyltriethoxysilane.
Claim 6
Dependent Claim
49 words
A coating composition as in claim 2 wherein said polyfunctional non-acrylate-functional ether is selected from the group consisting of compounds and mixtures of at least two of such compounds wherein each compound has at least one of the following moieties: glycidyl ether; allyl ether; vinyl ether; and cycloaliphatic epoxide.
Claim 7
Dependent Claim
25 words
A coating composition as in claim 2 wherein said polyfunctional, non-acrylate-functional ether comprises a mixture of a triglycidyl ether and a polyethylene glycol divinyl ether.
Claim 8
Dependent Claim
23 words
A coating composition as in claim 2 wherein said polyfunctional, non-acrylate-functional ether comprises a mixture of a triglycidyl ether and a polyallyl-functional ether.
Claim 9
Dependent Claim
21 words
A coating composition as in claim 7 wherein said polyfunctional, non-acrylate-functional ether comprises a mixture of a triglycidyl ether and tetraallyloxyethane.
Claim 10
Dependent Claim
23 words
A coating composition as in claim 2 wherein said polyfunctional, non-acrylate-functional ether comprises a mixture of a triglycidyl ether and a cycloaliphatic diepoxide.
Claim 11
Dependent Claim
25 words
A coating composition as in claim 2 wherein said polyfunctional, non-acrylate-functional ether comprises a mixture of a polyethylene glycol divinyl ether and a cycloaliphatic diepoxide.
Claim 12
Dependent Claim
43 words
A coating composition as in claim 3 wherein said monofunctional monomer is selected from the group consisting of vinyl acetate, phenyl allyl ether, 2-hydroxy ethyl acrylate, tetrahydrofurfuryl acrylate, tetrahydrofurfuryl methacrylate, methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, and propyl methacrylate.
Claim 13
Dependent Claim
14 words
A coating composition as in claim 2 which additionally comprises a multifunctional acrylate monomer.
Claim 14
Dependent Claim
18 words
A coating composition as in claim 12 wherein said multifunctional acrylate monomer does not contain a silyl moiety.
Claim 15
Dependent Claim
96 words
A coating composition as in claim 2 wherein said radiation-sensitive initiator is an aromatic onium salt having a formula: (R¹⁰ -C₆H₄) n X n ⁺MQ h - wherein X is a radical selected from I, P or S; and M is a metal or metalloid and Q is a halogen radical selected from Cl, F, Br, or I; R¹⁰ is hydrogen or a monovalent hydrocarbon radical having 1 to 12 carbon atoms, h is an integer having a value of 4 to 6 inclusive, and n is an integer having a value of 2 or 3.
Claim 16
Dependent Claim
26 words
A coating composition as in claim 14 wherein said initiator is present in an amount from about 0.05 to about 10 percent of the total mixture.
Claim 17
Dependent Claim
31 words
A coating composition as in claim 14 wherein said initiator is further combined with a radical-type photoinitiator in an amount from about 0.5 to about 10 percent of the total mixture.
Claim 18
Dependent Claim
28 words
A coating composition as in claim 16 wherein said radical-type photoinitiator is selected from the group consisting of benzophenone, ethyl benzoin ether, isopropyl benzoin ether, dimethoxyphenylacetophenone, and diethoxyacetophenone.
Claim 19
Dependent Claim
43 words
A coating composition as in claim 2 wherein said silane compound is 3-glycidoxypropyltrimethoxysilane, said initiator is triphenylsulfonium hexafluoroantimonate, and said ether is a triglycidyl ether which is present in an amount from about 0.1 to about 1.0 parts per each part colloidal silica.
Claim 20
Dependent Claim
25 words
A coating composition as in claim 18 which additionally comprises from about 0.1 to about 1.5 parts per each part colloidal silica of vinyl acetate.
Claim 21
Dependent Claim
65 words
A coating composition as in claim 12 wherein said silane compound is 3-glycidoxypropyltrimethoxysilane, said initiator is a combination of benzophenone and triphenylsulfonium hexafluoroantimonate, said ether is a triglycidyl ether which is present in an amount from about 0.1 to about 1.0 parts per each part colloidal silica, and additionally comprising from about 0.05 to about 1.5 parts per each part colloidal silica of trimethylolpropane triacrylate.
Claim 22
Dependent Claim
25 words
A coating composition as in claim 20 which additionally comprises from about 0.1 to about 1.5 parts per each part colloidal silica of vinyl acetate.
Claim 23
Dependent Claim
58 words
A coating composition as in claim 16 wherein said silane compound is gamma-methacryloxypropyltrimethoxy-silane, said initiator is a combination of triphenylsulfonium hexafluoroantinonate and benzophenone, and said ether is a mixture of a triglycidyl ether and 1, 1, 2, 2 - tetraallyloxyethane which is present in an amount from about 0.1 to about 1.0 parts per each part colloidal silica.
Claim 24
Dependent Claim
25 words
A coating composition as in claim 22 which additionally comprises from about 0.1 to about 1.5 parts per each part colloidal silica of vinyl acetate.
Claim 25
Dependent Claim
44 words
An article made by applying to at least one surface of a substrate a radiation-curable coating composition as claimed in any of claims 1-23 and curing said coating composition by exposing said composition to high intensity irradiation to form a transparent, abrasion-resistant, tintable coating.
Claim 26
Dependent Claim
15 words
An article as set forth in claim 24 wherein said substrate is a polycarbonate lens.
Claim 27
Dependent Claim
32 words
An article as set forth in claim 24 wherein said substrate is selected from the group consisting of a glass lens, an acrylic plastic, a polyethylene terphthalate film, and a polyester film.
Claim 28
Dependent Claim
78 words
A process for tinting the surface of a substrate by applying to at least one surface of said substrate a radiation-curable coating composition as claimed in any of claims 1-23, curing said coating composition by exposing said composition to high intensity irradiation to form a transparent, abrasion-resistant, tintable coating, and then immersing said coated surface of said substrate in a dye bath for a period of time sufficient for said coating to absorb a desired amount of dye.
References Cited (Backward Citations)
No citation records indexed.
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