US4486504A
Expired / Lapsed
US
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Solventless, ultraviolet radiation-curable silicone coating compositions
Assignee: General Electric Co
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Filing: 1982-03-19
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Granted: 1984-12-04
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Expires: 2002-03-19
Abstract
Abstract An ultraviolet radiation-curable silicone coating composition is disclosed which, when applied to a solid substrate, provides an abrasion-resistant coating firmly adhered thereon. The silicone coating composition is free of residual solvent and free of toxic hydroxy acrylates, and is prepared from the hydrolysis products of acryloxy-functional silanes and/or glycidoxy-functional silanes, colloidal silica and a photoinitiator.
Inventors
- 👤 Rack H. Chung
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 10:27
CPC Classifications
C; C09; C09D; C09D4/00; C09D4/06; C08; C08F; C08F290/00; C08F290/08; C08F290/14; C08F290/148; C08F299/00; C08F299/02; C08F299/08; C09D183/00; C09D183/04; C09D183/06; Y; Y10; Y10S; Y10S522/00; Y10S522/907; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31507; Y10T428/31511; Y10T428/31529; Y10T428/31652; Y10T428/31663
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
203 words
A solventless ultraviolet radiation-curable coating composition free of hydroxy acrylates comprising: (A) 100 parts by weight silica in the form of a colloidal dispersion; (B) 5 to 500 parts by weight of an acid hydrolysis product of (i) an acryloxy-functional silane having a general formula: ##STR9## wherein R 3 and R 4 are the same or different monovalent hydrocarbon radicals, R 5 is a divalent hydrocarbon radical having from 2 to 8 carbon atoms, R 6 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) a glycidoxy-functional silane having a general formula: ##STR10## wherein R 7 and R 8 are the same or different monovalent hydrocarbon radicals, R 9 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) a mixture of (i) and (ii); and (C) a catalytic amount of an ultraviolet light sensitive photoinitiator or mixture of photoinitiators; wherein residual solvent has been removed from said coating composition at reduced pressure.
Claim 2
Dependent Claim
203 words
A solventless ultraviolet radiation-curable coating composition free of hydroxy acrylates comprising: (A) 100 parts by weight silica in the form of a colloidal dispersion; (B) 5 to 500 parts by weight of an acid hydrolysis product of (i) an acryloxy-functional silane having a general formula: ##STR9## wherein R 3 and R 4 are the same or different monovalent hydrocarbon radicals, R 5 is a divalent hydrocarbon radical having from 2 to 8 carbon atoms, R 6 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) a glycidoxy-functional silane having a general formula: ##STR10## wherein R 7 and R 8 are the same or different monovalent hydrocarbon radicals, R 9 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) a mixture of (i) and (ii); and (C) a catalytic amount of an ultraviolet light sensitive photoinitiator or mixture of photoinitiators; wherein residual solvent has been removed from said coating composition at reduced pressure.
Claim 3
Dependent Claim
21 words
A composition as defined in claim 1 which additionally contains 10 to 500 parts by weight of a non-silyl, non-hydroxy acrylate.
Claim 4
Dependent Claim
27 words
A composition as defined in claim 1 or 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-acryloxyethyltriethoxysilane.
Claim 5
Dependent Claim
24 words
A composition as defined in claim 1 or 2 wherein said glycidoxy-functional silane is selected from the group consisting of: 3-glycidoxypropyltrimethoxysilane 2-glycidoxyethyltrimethoxysilane 3-glycidoxypropyltriethoxysilane 2-glycidoxyethyltriethoxysilane.
Claim 6
Dependent Claim
35 words
A composition as defined in claim 2 wherein said non-silyl acrylate is selected from the group consisting of: diethylene glycol diacrylate triethylene glycol diacrylate tetraethylene glycol diacrylate trimethylol propane triacrylate tetrahydro furfuryl methacrylate 1-6-hexanediol diacrylate.
Claim 7
Dependent Claim
93 words
A composition as defined in claim 1 or 2 wherein said photoinitiator is a radiation sensitive aromatic onium salt having the formula: ##STR11## 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; R 10 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 8
Dependent Claim
31 words
A composition as defined in claim 6 wherein MQ h - is selected from SbF 6 - , AsF 6 - , BF 4 - , and PF 6 - .
Claim 9
Dependent Claim
22 words
A composition as defined in claim 6 wherein said photoinitiator is further combined with 0.5 to 5.0 parts of a radical-type photoinitiator.
Claim 10
Dependent Claim
22 words
A composition as in claim 8 wherein said radical-type photoinitiator is selected from ethyl benzoin ether, isopropyl benzoin ether, dimethoxyphenylacetophenone and diethoxyacetophenone.
Claim 11
Dependent Claim
22 words
A composition as defined in claim 1 or 2 which also contains a small amount of polysiloxane polyether copolymer flow control additive.
Claim 12
Dependent Claim
32 words
A composition as defined in claim 1 or 2 which additionally contains a photo-modifiable compound which is capable of converting to an ultraviolet radiation screening agent upon curing of the coating composition.
Claim 13
Dependent Claim
23 words
A composition as defined in claim 11 wherein the photo-modifiable compound has the formula: ##STR12## where R is hydrogen (H) or methyl (Me).
Claim 14
Dependent Claim
201 words
A process for preparing a solventless ultraviolet radiation curable coating composition free of hydroxy acrylates comprising: (1) Combining (A) 100 parts by weight silica in the form of a colloidal dispersion; (B) 5 to 500 parts by weight of the acid hydrolysis product of (i) an acryloxy-functional silane of the formula: ##STR13## wherein R 3 and R 4 are the same or different monovalent hydrocarbon radicals, R 5 is a divalent hydrocarbon radical having from 2 to 8 carbon atoms, R 6 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 equal to 4-b-c; or (ii) a glycydoxy-functional silane of the formula: ##STR14## wherein R 7 and R 8 are the same or different monovalent hydrocarbon radicals, R 9 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 equal to 4-e-f; or (iii) mixtures of (i) and (ii); (2) adding a catalytic amount of an ultraviolet light sensitive photoinitiator; and thereafter (3) removing residual solvent at reduced pressure.
Claim 15
Dependent Claim
201 words
A process for preparing a solventless ultraviolet radiation curable coating composition free of hydroxy acrylates comprising: (1) Combining (A) 100 parts by weight silica in the form of a colloidal dispersion; (B) 5 to 500 parts by weight of the acid hydrolysis product of (i) an acryloxy-functional silane of the formula: ##STR13## wherein R 3 and R 4 are the same or different monovalent hydrocarbon radicals, R 5 is a divalent hydrocarbon radical having from 2 to 8 carbon atoms, R 6 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 equal to 4-b-c; or (ii) a glycydoxy-functional silane of the formula: ##STR14## wherein R 7 and R 8 are the same or different monovalent hydrocarbon radicals, R 9 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 equal to 4-e-f; or (iii) mixtures of (i) and (ii); (2) adding a catalytic amount of an ultraviolet light sensitive photoinitiator; and thereafter (3) removing residual solvent at reduced pressure.
Claim 16
Dependent Claim
24 words
The process of claim 13 which contains the additional step, before step (2), of adding 10-500 parts by weight of a non-silyl, non-hydroxy acrylate.
Claim 17
Dependent Claim
20 words
The process of claim 13 or 14 which also contains a small amount of polysiloxane polyether copolymer flow control additive.
Claim 18
Dependent Claim
30 words
The process of claims 13 or 14 which additionally contains a photo-modifiable compound which is capable of converting to an ultraviolet radiation screening agent upon curing of the coating composition.
Claim 19
Dependent Claim
21 words
The process of claim 16 wherein the photo-modifiable compound has the formula: ##STR15## where R is hydrogen (H) or methyl (Me).
Claim 20
Dependent Claim
8 words
The cured product of claim 1 or 2.
Claim 21
Dependent Claim
18 words
A solid substrate having at least one surface coated with the coating composition of claim 1 or 2.
Claim 22
Dependent Claim
18 words
An article as defined in claim 19 wherein the solid substrate is comprised of a synthetic organic polymer.
Claim 23
Dependent Claim
14 words
An article as defined in claim 19 wherein said solid substrate is a metal.
Claim 24
Dependent Claim
20 words
An article as defined in claim 19 wherein said solid substrate is a synthetic organic polymer having a metallized surface.
Claim 25
Dependent Claim
14 words
An article as defined in claim 20 wherein said polymer is a transparent polymer.
Claim 26
Dependent Claim
13 words
An article as defined in claim 20 wherein said polymer is a polycarbonate.
Claim 27
Dependent Claim
12 words
An article as defined in claim 24 wherein said polycarbonate is transparent.
Claim 28
Dependent Claim
15 words
An article as defined in claim 24 wherein said polycarbonate is a poly (bisphenol-A carbonate).
Claim 29
Dependent Claim
28 words
An article as defined in claim 19 wherein the coating composition has been cured on said surface of said solid substrate by an effective amount of ultraviolet radiation.
Claim 30
Dependent Claim
25 words
An article as defined in claim 19 wherein said surface of said solid substrate has been primed with a primer composition prior to being coated.
Claim 31
Dependent Claim
18 words
An article as defined in claim 28 wherein said primer composition is comprised of a thermosetting acrylic emulsion.
Claim 32
Dependent Claim
12 words
An article as defined in claim 20 wherein said polymer is polymethylmethacrylate.
References Cited (Backward Citations)
US3629165A
Cited
US3865588A
Cited
US3708225A
Cited
US4136102A
Cited
US4027073A
Cited
US3986997A
Cited
US3976497A
Cited
US3981897A
Cited
US4101513A
Cited
US4156035A
Cited
US4222835A
Cited
US4250203A
Cited
US4348462A
Cited
US4310600A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-12-04 | 1988-06-04 | 1988-12-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-12-04 | 1992-06-04 | 1992-12-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-12-04 | 1996-06-04 | 1996-12-04 | $7700.00 | Window Closed / Lapsed |