US4370358A
Expired / Lapsed
US
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Ultraviolet curable silicone adhesives
Assignee: General Electric Co
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Filing: 1980-09-22
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Granted: 1983-01-25
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Expires: 2000-09-22
Abstract
Abstract An ultraviolet light curable silicone pressure sensitive adhesive is provided which is comprised of an epoxy functional silicone polymer and a combination of standard MQ silicone resins or epoxy functional MQ silicone resins, which can be cured to an adhesive composition in the presence of certain bis(aryl)halonium salt catalysts.
Inventors
- 👤 Susan E. Hayes
- 👤 Richard P. Eckberg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 11:47
CPC Classifications
C; C08; C08L; C08L83/00; C08L83/04; C08L83/06; C09; C09J; C09J183/00; C09J183/04; C09J183/06; C08L2666/00; C08L2666/28; Y; Y10; Y10T; Y10T428/00; Y10T428/28; Y10T428/2852; Y10T428/2857; Y10T428/287; Y10T428/31504; Y10T428/31652; Y10T428/31663
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
246 words
A solventless ultraviolet radiation curable composition for forming a pressure sensitive silicone adhesive comprised of: (a) 100 parts by weight of an epoxy functional silicone polymer having the general formula: ##STR7## wherein R is a monovalent hydrocarbon radical, and R' is the same as R or a phenyl radical and R" is an epoxy-containing aliphatic or cycloaliphatic radical; having, approximately, 0.01 to 0.05 mole % epoxy content and a viscosity of, approximately, 100 to 5000 centipoise at 25° C., χ is an integer representing 85 to 100 mole percent of the polymer units and y represents 0 to 15 mole percent diphenyl siloxy units; (b) 90 to 280 parts by weight of a silicone MQ resin or mixture of such resins selected from: (i) a first silicone resin comprised of mono-functional R 3 SiO 0 .5 units and tetra-functional SiO 2 units where R is as described above and the ratio of mono-functional units to tetra-functional units is, approximately, 0.5 to 2.0:1; or (ii) a second silicone resin comprised of R a R b "SiO 0 .5 units and SiO 2 units wherein R is as described above and R" represents aliphatic or cycloaliphatic epoxide radicals; having, approximately, 0 to 0.005 mole % epoxy content, the sum of a band b is 3, and wherein the ratio of mono-functional to tetra-functional units is approximately 0.5 to 2.0:1, and (c) an amount of ultraviolet light sensitive catalyst effective for initiating the cure of said silicone adhesive composition.
Claim 2
Dependent Claim
246 words
A solventless ultraviolet radiation curable composition for forming a pressure sensitive silicone adhesive comprised of: (a) 100 parts by weight of an epoxy functional silicone polymer having the general formula: ##STR7## wherein R is a monovalent hydrocarbon radical, and R' is the same as R or a phenyl radical and R" is an epoxy-containing aliphatic or cycloaliphatic radical; having, approximately, 0.01 to 0.05 mole % epoxy content and a viscosity of, approximately, 100 to 5000 centipoise at 25° C., χ is an integer representing 85 to 100 mole percent of the polymer units and y represents 0 to 15 mole percent diphenyl siloxy units; (b) 90 to 280 parts by weight of a silicone MQ resin or mixture of such resins selected from: (i) a first silicone resin comprised of mono-functional R 3 SiO 0 .5 units and tetra-functional SiO 2 units where R is as described above and the ratio of mono-functional units to tetra-functional units is, approximately, 0.5 to 2.0:1; or (ii) a second silicone resin comprised of R a R b "SiO 0 .5 units and SiO 2 units wherein R is as described above and R" represents aliphatic or cycloaliphatic epoxide radicals; having, approximately, 0 to 0.005 mole % epoxy content, the sum of a band b is 3, and wherein the ratio of mono-functional to tetra-functional units is approximately 0.5 to 2.0:1, and (c) an amount of ultraviolet light sensitive catalyst effective for initiating the cure of said silicone adhesive composition.
Claim 3
Dependent Claim
26 words
A composition as in claim 1 wherein said epoxy functional silicone polymer contains epoxide radicals introduced from a compound selected from 4-vinylcyclohexeneoxide, vinylnorbornenemonoxide, dicyclopentadienemonoxide and limoneneoxide.
Claim 4
Dependent Claim
20 words
A composition as in claim 2 wherein said epoxy functional silicone polymer is dimethyl-β-(3,4-epoxycyclohexyl)ethyl silyl chainstopped poly dimethyl-diphenyl siloxane copolymer.
Claim 5
Dependent Claim
93 words
A composition as in claim 1 wherein said catalyst is 0.2 to 10 parts by weight per 100 parts epoxy functional silicone polymer of a halonium salt of the formula: ##STR8## wherein R 4 is a linear alkylate monovalent hydrocarbon radical containing an average of 12 carbon atoms, J is a metal or metalloid, K is a halogen radical, e is an integer representing the valence of J and is equal to 2 to 7 inclusive, d is an integer having a value up to 8 such that d is greater than e.
Claim 6
Dependent Claim
43 words
A composition as in claim 4 wherein said catalyst is selected from linear alkylate halonium salts of the average formula: ##STR9## wherein Z is selected from the group consisting of AsF 6 , SbF 6 , BF 4 , and PF 6 .
Claim 7
Dependent Claim
9 words
A substrate coated with the composition of claim 1.
Claim 8
Independent Claim
254 words
A method for providing a solventless ultraviolet radiation curable composition for forming a pressure sensitive silicone adhesive comprising the steps of combining: (a) 100 parts by weight of an epoxy functional silicone polymer having the general average formula: ##STR10## wherein R is a monovalent hydrocarbon radical and R' is the same as R or a phenyl radical and R" is an epoxy-containing aliphatic or cycloaliphatic radical; having, approximately, 0.01 to 0.05 mole % epoxy content and a viscosity of, approximately, 100 to 5000 centipoise at 25° C., χ is an integer representing 85 to 100 mole percent of the polymer units and y represents 0 to 15 mole percent diphenyl siloxy units; (b) 90 to 280 parts by weight of a silicone MQ resin or mixture of such resins selected from: (i) a first silicone resin comprised of mono-functional R 3 SiO 0 .5 units and tetra-functional SiO 2 units where R is as described above and the ratio of mono-functional units to tetra-functional units is, approximately, 0.5 to 2.0:1, or (ii) a second silicone resin comprised of R a R b "SiO 0 .5 units and SiO 2 units wherein R is as described above and R" represents aliphatic or cycloaliphatic epoxide radicals; having, approximately, 0 to 0.005 mole % epoxy content, the sum of a and b is 3, and wherein the ratio of mono-functional to tetra-functional units is approximately 0.5 to 2.0:1, and (c) an amount of ultraviolet light sensitive catalyst effective for initiating the cure of said silicone adhesive composition.
Claim 9
Independent Claim
254 words
A method for providing a solventless ultraviolet radiation curable composition for forming a pressure sensitive silicone adhesive comprising the steps of combining: (a) 100 parts by weight of an epoxy functional silicone polymer having the general average formula: ##STR10## wherein R is a monovalent hydrocarbon radical and R' is the same as R or a phenyl radical and R" is an epoxy-containing aliphatic or cycloaliphatic radical; having, approximately, 0.01 to 0.05 mole % epoxy content and a viscosity of, approximately, 100 to 5000 centipoise at 25° C., χ is an integer representing 85 to 100 mole percent of the polymer units and y represents 0 to 15 mole percent diphenyl siloxy units; (b) 90 to 280 parts by weight of a silicone MQ resin or mixture of such resins selected from: (i) a first silicone resin comprised of mono-functional R 3 SiO 0 .5 units and tetra-functional SiO 2 units where R is as described above and the ratio of mono-functional units to tetra-functional units is, approximately, 0.5 to 2.0:1, or (ii) a second silicone resin comprised of R a R b "SiO 0 .5 units and SiO 2 units wherein R is as described above and R" represents aliphatic or cycloaliphatic epoxide radicals; having, approximately, 0 to 0.005 mole % epoxy content, the sum of a and b is 3, and wherein the ratio of mono-functional to tetra-functional units is approximately 0.5 to 2.0:1, and (c) an amount of ultraviolet light sensitive catalyst effective for initiating the cure of said silicone adhesive composition.
Claim 10
Dependent Claim
26 words
A method as in claim 7 wherein said epoxy functional silicone polymer contains epoxide radicals introduced from a compound selected from 4-vinylcyclohexeneoxide, vinylnorbornenemonoxide, dicyclopentadienemonoxide and limoneneoxide.
Claim 11
Dependent Claim
20 words
A method as in claim 10 wherein said epoxy functional silicone polymer is dimethyl-β-(3,4-epoxycyclohexyl)ethyl silyl chainstopped poly dimethyl-diphenyl siloxane copolymer.
Claim 12
Dependent Claim
93 words
A method as in claim 8 wherein said catalyst is 0.2 to 10 parts by weight per 100 parts epoxy functional silicone polymer of a halonium salt of the formula: ##STR11## wherein R 4 is a linear alkylate monovalent hydrocarbon radical containing an average of 12 carbon atoms, J is a metal or metalloid, K is a halogen radical, e is an integer representing the valence of J and is equal to 2 to 7 inclusive, d is an integer having a value up to 8 such that d is greater than e.
Claim 13
Dependent Claim
43 words
A method as in claim 10 wherein said catalyst is selected from linear alkylate halonium salts of the average formula: ##STR12## wherein Z is selected from the group consisting of AsF 6 , SbF 6 , BF 4 , and PF 6 .
Claim 14
Independent Claim
200 words
A method of providing a solventless ultraviolet radiation curable composition for forming a silicone pressure sensitive adhesive comprising the steps of partially crosslinking a dimethylhydrogen chainstopped polydimethylsiloxane precursor fluid with up to approximately 0.005 moles of an unsaturated siloxane composition; reacting said partially crosslinked precursor fluid with an epoxy-containing aliphatic or cycloaliphatic species thereby providing a partially crosslinked epoxy functional silicone fluid; combining said epoxy functional fluid with a silicone MQ resin or mixture of such resins selected from: (i) a first silicone resin comprised of mono-functional R 3 SiO 0 .5 units and tetra-functional SiO 2 units where R is as described above and the ratio of mono-functional units to tetra-functional units is, approximately, 0.5 to 2.0:1, or (ii) a second silicone resin comprised of R a R b "SiO 0 .5 units and SiO 2 units wherein R is as described above R" represents aliphatic or cycloaliphatic epoxide radicals; having, approximately, 0 to 0.005 mole % epoxy content, the sum of a and b is 3, and wherein the ratio of mono-functional to tetra-functional units is approximately 0.5 to 2.0:1; and adding an amount of ultraviolet light sensitive catalyst effective for initiating the cure of said curable composition.
Claim 15
Independent Claim
200 words
A method of providing a solventless ultraviolet radiation curable composition for forming a silicone pressure sensitive adhesive comprising the steps of partially crosslinking a dimethylhydrogen chainstopped polydimethylsiloxane precursor fluid with up to approximately 0.005 moles of an unsaturated siloxane composition; reacting said partially crosslinked precursor fluid with an epoxy-containing aliphatic or cycloaliphatic species thereby providing a partially crosslinked epoxy functional silicone fluid; combining said epoxy functional fluid with a silicone MQ resin or mixture of such resins selected from: (i) a first silicone resin comprised of mono-functional R 3 SiO 0 .5 units and tetra-functional SiO 2 units where R is as described above and the ratio of mono-functional units to tetra-functional units is, approximately, 0.5 to 2.0:1, or (ii) a second silicone resin comprised of R a R b "SiO 0 .5 units and SiO 2 units wherein R is as described above R" represents aliphatic or cycloaliphatic epoxide radicals; having, approximately, 0 to 0.005 mole % epoxy content, the sum of a and b is 3, and wherein the ratio of mono-functional to tetra-functional units is approximately 0.5 to 2.0:1; and adding an amount of ultraviolet light sensitive catalyst effective for initiating the cure of said curable composition.
Claim 16
Dependent Claim
9 words
The cured curable composition of claims 1 and 6.
Claim 17
Dependent Claim
55 words
A method as in claim 7 or 12 further comprising the steps of: coating said curable composition on a substrate selected from paper, plastic, metal or glass substrates; and exposing said coated silicone adhesive composition with an amount of ultraviolet radiation effective for facilitating a cure reaction of said silicone adhesive composition on said substrate.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-01-24 | 1986-07-26 | 1987-01-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-01-24 | 1990-07-26 | 1991-01-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-01-24 | 1994-07-26 | 1995-01-25 | $7700.00 | Window Closed / Lapsed |