US4698113A
Expired / Lapsed
US
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Method of curing photocurable and heat-curable compositions and a method of adhering members to each other by using them
Assignee: Panasonic Holdings Corp
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Filing: 1985-04-08
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Granted: 1987-10-06
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Expires: 2005-04-08
Abstract
Abstract A method of curing photocurable and heat-curable compositions for adhering optical elements to each other which consist of, as major components, a polyfunctional acrylate and a polythiol, a radical type photocuring initiator, a radical type heat-curing initiator and a stabilizer and a method of adhering the optical elements to each other by using them are provided.
Inventors
- 👤 Kazufumi Ogawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 04:42
CPC Classifications
C; C09; C09J; C09J5/00; C09J5/06
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
133 words
A method of adhering a color filter having a transparent region for passing light rays therethrough in at least a part thereof to a solid-state image sensor, wherein said filter and said sensor are maintained in accurate alignment during the adhering method, comprising superimposing said color filter on said solid-state image sensor with a photocurable and heat-curable adhesive sandwiched therebetween; aligning said color filter and said solid-state image sensor to form an assembly; irradiating said aligned assembly with light, to precure at least a part of the adhesive beneath said transparent region by means of light rays passing through said transparent region, to fix said color filter and solid-state image sensor in position; and while said filter and said sensor are fixed in accurate alignment, heating said assembly to thermally cure the adhesive.
Claim 2
Independent Claim
133 words
A method of adhering a color filter having a transparent region for passing light rays therethrough in at least a part thereof to a solid-state image sensor, wherein said filter and said sensor are maintained in accurate alignment during the adhering method, comprising superimposing said color filter on said solid-state image sensor with a photocurable and heat-curable adhesive sandwiched therebetween; aligning said color filter and said solid-state image sensor to form an assembly; irradiating said aligned assembly with light, to precure at least a part of the adhesive beneath said transparent region by means of light rays passing through said transparent region, to fix said color filter and solid-state image sensor in position; and while said filter and said sensor are fixed in accurate alignment, heating said assembly to thermally cure the adhesive.
Claim 3
Dependent Claim
107 words
A method as set forth in claim 1, wherein said adhesive consists essentially of a polyfunctional acrylate and a polythiol, which are major components, a free radical generating photoinitiator, a free radical generating heat-activated curing initiator, and stabilizer, (A) said polyfunctional acrylate being selected from the group consisting of di-pentaerythritol hexacrylate, di-pentaerythritol pentacrylate or a mixture thereof, (b) said polythiol being selected from the group consisting of pentaerythritol tetrakis(thioglycolate), trimethylol ethanetris(β-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropylether), a mixture consisting of any two of the above mentioned compounds or a mixture of all of said compounds, the weight ratio of said polythiol to said polyfunctional acrylate being from 10:1 to 1:10.
Claim 4
Dependent Claim
69 words
A method as set forth in claim 2 wherein: (a) said polyfunctional acrylate is a mixture of dipentaerythritol hexacrylate and pentaerythritol pentacrylate; (b) said polythiol is pentaerythritol tetra-thiopropionate; (c) the weight ratio between said multi-sensitive acrylate and said polythiol is from 1:2 to 2:1, (d) said photocuring initiator is 0.1-10% by weight of 4'-isopropyl-2-hydroxy-2-methylpropiophenol, 2-hydroxy-2-methylpropiophenol, 2-hydroxy-2-methylpropiophenol or benzyldimethylketal; and (e) said heat-curing initiator is 1-10% by weight of benzopinacol.
Claim 5
Dependent Claim
21 words
A method as set forth in claim 2, wherein said polyfunctional acrylate is di-pentaerythritol hexacrylate, dipentaerythritol pentacrylate or a mixture thereof.
Claim 6
Dependent Claim
37 words
A method as set forth in claim 2, wherein said polythiol is pentaerythritol tetrakis(thioglycolate), trimethylol ethane tris(β-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropylether), a mixture consists of any two of the above-mentioned compounds or a mixture of all of said compounds.
Claim 7
Dependent Claim
17 words
A method as set forth in claim 2, wherein said photocuring initiator is 4'-isopropyl-2-hydroxy-2-methylpropiophenol, 2-hydroxy-2-methylpropiophenol or benzyldimethylketal.
Claim 8
Dependent Claim
19 words
A method as set forth in claim 2, wherein said stabilizer is phosphorus acid, pyrogallol, 2,6-di-t-butyl-4-methylphenol, hydroquinone, or phenothiazine.
Claim 9
Dependent Claim
23 words
A method as set forth in claim 2, wherein said photocuring initiator is 4'-isopropyl-2-hydroxy-2-methylpropiophenol, 2-hydroxy-2-methylpropiophenol or benzyldimethylketal, in an amount 0.1-10% by weight.
Claim 10
Dependent Claim
22 words
A method as set forth in claim 8, further characterized in that said heating curing initiator is 1-10% by weight of benzopinacol.
Claim 11
Dependent Claim
19 words
A method as set forth in claim 9, wherein said stabilizer is phosphorus acid, pyrogallol, 2,6-di-t-butyl-4-methylphenol, hydroquinone, or phenothiazine.
Claim 12
Dependent Claim
55 words
A method as set forth in claim 2, wherein said adhesive consists essentially of d-pentaerythritol hexacrylate and pentaerythritol tetra-thiopropionate in a weight ratio of 1:1 to 0.8:1, 1-5% by weight of 4'-isopropyl-2-hydroxy-2-methylpropiophenol, 2-hydroxy-2-methylpropiophenol, or benzyldimethylketal; 1-5% by weight of benzopinacol; and an effective amount of phosphorous acid, pyrogallol, 2,6-di-t-butylmethylphenol, hydroquinone, or phenothiazine, as a stabilizer.
Claim 13
Dependent Claim
159 words
A method as set forth in claim 1, wherein said adhesive consists essentially of a polyfunctional acrylate and a polythiol, which are major components, a free radical generating photoinitiator, a free radical generating heat-activated curing initiator, and a stabilizer, (A) said polyfunctional acrylate being selected from the group consisting of di-pentaerythritol hexacrylate, di-pentaerythritol pentacrylate or a mixture thereof, (B) said polythiol being selected from the group consisting of pentaerythritol tetrakis(thioglycolate), trimethylol ethane tris(β-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropylether), a mixture consisting of any two of the above mentioned compounds or a mixture of all of said compounds, the weight ratio of said polythiol to said polyfunctional acrylate being from 10:1 to 1:10, (C) said photoinitiator being selected from the group consisting of 4'-isopropyl-2-hydroxy-2-methylpropiophenol, 2-hydroxy-2-methylpropiophenol or benzyldimethylketal, in an amount of 0.1-10% by weight, (D) said heat-activated curing initiator being 1-10% by weight of benzopinacol, and (E) said stabilizer being selected from the group consisting of phosphorus acid, pyrogallol, 2,6-di-t-butyl-4-methylphenol, hydroquinone, or phenothiazine.
Claim 14
Independent Claim
233 words
A method of adhering a color filter having a transparent region for passing light rays therethrough in at least a part thereof to a solid-state image sensor, wherein said filter and said sensor are maintained in accurate alignment during the adhering method, comprising superimposing said color filter on said solid-state image sensor with a photocurable and heat-curable adhesive sandwiched therebetween; said adhesive consisting essentially of a polyfunctional acrylate and a polythiol, which are major components, a free radical generating photoinitiator, a free radical generating heat-activated curing initiator, and a stabilizer, (A) said polyfunctional acrylate being selected from the group consisting of di-pentaerythritol hexacrylate, di-pentaerythritol pentacrylate or a mixture thereof, (B) said polythiol being selected from the group consisting of pentaerythritol tetrakis(thioglycolate), trimethylol ethane tris(β-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropylether), a mixture consisting of any two of the above mentioned compounds or a mixture of all of said compounds, the weight ratio of said polythiol to said polyfunctional acrylate being from 10:1 to 1:10; aligning said color filter and solid-state image sensor to form an assembly; irradiating said aligned assembly with light, to precure at least a part of the adhesive beneath said transparent region by means of light rays passing through said transparent region, to temporarily fix said color filter and solid-state image sensor in position; and while said filter and said sensor are fixed in accurate alignment, heating said assembly to thermally cure the adhesive.
Claim 15
Independent Claim
233 words
A method of adhering a color filter having a transparent region for passing light rays therethrough in at least a part thereof to a solid-state image sensor, wherein said filter and said sensor are maintained in accurate alignment during the adhering method, comprising superimposing said color filter on said solid-state image sensor with a photocurable and heat-curable adhesive sandwiched therebetween; said adhesive consisting essentially of a polyfunctional acrylate and a polythiol, which are major components, a free radical generating photoinitiator, a free radical generating heat-activated curing initiator, and a stabilizer, (A) said polyfunctional acrylate being selected from the group consisting of di-pentaerythritol hexacrylate, di-pentaerythritol pentacrylate or a mixture thereof, (B) said polythiol being selected from the group consisting of pentaerythritol tetrakis(thioglycolate), trimethylol ethane tris(β-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropylether), a mixture consisting of any two of the above mentioned compounds or a mixture of all of said compounds, the weight ratio of said polythiol to said polyfunctional acrylate being from 10:1 to 1:10; aligning said color filter and solid-state image sensor to form an assembly; irradiating said aligned assembly with light, to precure at least a part of the adhesive beneath said transparent region by means of light rays passing through said transparent region, to temporarily fix said color filter and solid-state image sensor in position; and while said filter and said sensor are fixed in accurate alignment, heating said assembly to thermally cure the adhesive.
Claim 16
Independent Claim
206 words
A method of adhering a color filter having a transparent region for passing light rays therethrough in at least a part thereof to a solid state-image sensor, wherein said filter and said sensor are maintained in accurate alignment during the adhering method, comprising superimposing said color filter on said solid-state image sensor with a photocurable and heat-curable adhesive sandwiched therebetween, said adhesive consisting essentially of a polyfunctional acrylate and a polythiol, which are major components, a free radical generating photoinitiator, a free radical generating heat-activated curing initiator, and a stabilizer, (A) said polyfunctional acrylate being selected from the group consisting of: di-pentaerythritol hexacrylate, di-pentaerythritol pentacrylate or a mixture thereof, (B) said polythiol being selected from the group consisting of pentaerythritol tetrakis(thioglycolate), trimethylol ethane tris(β-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropylether), a mixture consisting of any two of the above mentined compounds or a mixture of all of said compounds, the weight ratio of said polythiol to said polyfunctional acrylate being from 10:1 to 1:10, (C) said photoinitiator being selected from the group consisting of 4'-isopropyl-2-hydroxy-2-methylpropiophenol, 2-hydroxy-2-methylpropiophenol or benzyldimethylketal, in an amount of 0.1-10% by weight, (D) said heat-activated curing initiator being 1-10% by weight of benzopinacol, and (E) said stabilizer being selected from the group consisting of phosphorus acid, pyrogallol,
Claim 17
Independent Claim
206 words
A method of adhering a color filter having a transparent region for passing light rays therethrough in at least a part thereof to a solid state-image sensor, wherein said filter and said sensor are maintained in accurate alignment during the adhering method, comprising superimposing said color filter on said solid-state image sensor with a photocurable and heat-curable adhesive sandwiched therebetween, said adhesive consisting essentially of a polyfunctional acrylate and a polythiol, which are major components, a free radical generating photoinitiator, a free radical generating heat-activated curing initiator, and a stabilizer, (A) said polyfunctional acrylate being selected from the group consisting of: di-pentaerythritol hexacrylate, di-pentaerythritol pentacrylate or a mixture thereof, (B) said polythiol being selected from the group consisting of pentaerythritol tetrakis(thioglycolate), trimethylol ethane tris(β-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropylether), a mixture consisting of any two of the above mentined compounds or a mixture of all of said compounds, the weight ratio of said polythiol to said polyfunctional acrylate being from 10:1 to 1:10, (C) said photoinitiator being selected from the group consisting of 4'-isopropyl-2-hydroxy-2-methylpropiophenol, 2-hydroxy-2-methylpropiophenol or benzyldimethylketal, in an amount of 0.1-10% by weight, (D) said heat-activated curing initiator being 1-10% by weight of benzopinacol, and (E) said stabilizer being selected from the group consisting of phosphorus acid, pyrogallol,
Claim 18
Dependent Claim
76 words
6-di-t-butyl-4-methylphenol, hydroquinone, or phenothiazine; aligning said color filter and solid-state image sensor to form an assembly; irradiating said aligned assembly with light, to precure at least a part of the adhesive beneath said transparent region by means of light rays passing through said transparent region, to fix said color filter and solid-state image sensor in position; and while said filter and said sensor are fixed in accurate alignment, heating said assembly to thermally cure the adhesive.
Claim 19
Dependent Claim
76 words
6-di-t-butyl-4-methylphenol, hydroquinone, or phenothiazine; aligning said color filter and solid-state image sensor to form an assembly; irradiating said aligned assembly with light, to precure at least a part of the adhesive beneath said transparent region by means of light rays passing through said transparent region, to fix said color filter and solid-state image sensor in position; and while said filter and said sensor are fixed in accurate alignment, heating said assembly to thermally cure the adhesive.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-10-05 | 1991-04-06 | 1991-10-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-10-05 | 1995-04-06 | 1995-10-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-10-05 | 1999-04-06 | 1999-10-06 | $7700.00 | Window Closed / Lapsed |