Patent US4272586A successfully refreshed from Google Patents.
US4272586A
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US
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Laminated glass product
Assignee: Denka Co Ltd
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Filing: 1979-01-31
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Granted: 1981-06-09
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Expires: 1999-01-31
Abstract
Abstract A laminated glass product has a bonding layer formed by curing a photocurable composition comprising a polyene, a polythiol and a photocuring rate accelerator, if necessary, an organosilane.
Inventors
- 👤 Toshihiro Ando
- 👤 Hiroshi Ohgi
- 👤 Ikuji Kishi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 14:26
CPC Classifications
C; C08; C08G; C08G75/00; C08G75/02; C08G75/04; C08G75/045; B; B32; B32B; B32B17/00; B32B17/06; B32B17/10; B32B17/10005; B32B17/1055; B32B17/10706; C08G75/12; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31533; Y10T428/31551; Y10T428/31609; Y10T428/31612; Y10T428/31645; Y10T428/31649; Y10T428/31652; Y10T428/31663
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
373 words
A laminated glass product having a bonding layer formed by curing a photocurable composition comprising a polyene component, a polythiol component, an organosilicone compound and a photocuring rate accelerator; wherein (A) said polyene is a compound having the formula ##STR11## wherein m is an integer of 2 to 6; R represents a hydrogen atom, a C 1 -C 8 alkyl, a C 1 -C 3 alkoxy or phenyl group which can be substituted with a substituent of nitro, C 1 -C 8 alkyl or alkoxy group or a halogen atom; Y is --CH 2 ) n wherein n is 0 or an integer of 1 to 10, --OCH 2 ) p wherein p is an integer of 1 to 10, --O--CH 2 ) q wherein q is an integer of 1 to 10 or ##STR12## and X is a polyvalent group which has a valency of m representing benzene, toluene, ethylene glycol, diethylene glycol, triethylene glycol, trimethylolpropane, phthalate, cyanurate, isocyanurate, trimellitate, ethane, N,N-piperazine, orthosilicate, phosphate, oxalate, terephthalate, diphenylterephthalate or methylenediamine group; (B) said polythiol is a compound having the formula ##STR13## wherein Z is a group connecting m' members and is --CH 2 ) v , ##STR14## wherein v is an integer of 1 to 6, and w, x, y and z are respectively 0 or an integer of 2 to 6; m' is an integer of 2 to 4; n' and p' are respectively 0 or an integer of 1 to 3; said polythiol having an average molecular weight of 50 to 15,000; (C) said organosilicone compound is a compound having the formula ##STR15## wherein n" is 0 or an integer of 1 to 3; X represents chlorine atom or a C 1 -C 8 alkoxy or acetoxy group which can be substituted by chlorine atom, nitro group or a C 1 -C 2 alkoxy group; and Y represents vinyl group which can be substituted by chlorine atom, methoxy, ethoxy, propyloxy or acetoxy; or acryloyl, methacryloyl or mercaptan group; and (D) said photocuring rate accelerator is selected from the group consisting of benzophenone, p-methoxybenzophenone, acetophenone, m-chloroacetophenone, propiophenone, xanthone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl benzaldehyde, naphthoquinone, anthraquinone, 2,4,7-trinitro-9-fluorenone, 5-nitro-acenaphthene, p-nitrodiphenyl, p-nitroaniline and malachite green.
Claim 2
Dependent Claim
373 words
A laminated glass product having a bonding layer formed by curing a photocurable composition comprising a polyene component, a polythiol component, an organosilicone compound and a photocuring rate accelerator; wherein (A) said polyene is a compound having the formula ##STR11## wherein m is an integer of 2 to 6; R represents a hydrogen atom, a C 1 -C 8 alkyl, a C 1 -C 3 alkoxy or phenyl group which can be substituted with a substituent of nitro, C 1 -C 8 alkyl or alkoxy group or a halogen atom; Y is --CH 2 ) n wherein n is 0 or an integer of 1 to 10, --OCH 2 ) p wherein p is an integer of 1 to 10, --O--CH 2 ) q wherein q is an integer of 1 to 10 or ##STR12## and X is a polyvalent group which has a valency of m representing benzene, toluene, ethylene glycol, diethylene glycol, triethylene glycol, trimethylolpropane, phthalate, cyanurate, isocyanurate, trimellitate, ethane, N,N-piperazine, orthosilicate, phosphate, oxalate, terephthalate, diphenylterephthalate or methylenediamine group; (B) said polythiol is a compound having the formula ##STR13## wherein Z is a group connecting m' members and is --CH 2 ) v , ##STR14## wherein v is an integer of 1 to 6, and w, x, y and z are respectively 0 or an integer of 2 to 6; m' is an integer of 2 to 4; n' and p' are respectively 0 or an integer of 1 to 3; said polythiol having an average molecular weight of 50 to 15,000; (C) said organosilicone compound is a compound having the formula ##STR15## wherein n" is 0 or an integer of 1 to 3; X represents chlorine atom or a C 1 -C 8 alkoxy or acetoxy group which can be substituted by chlorine atom, nitro group or a C 1 -C 2 alkoxy group; and Y represents vinyl group which can be substituted by chlorine atom, methoxy, ethoxy, propyloxy or acetoxy; or acryloyl, methacryloyl or mercaptan group; and (D) said photocuring rate accelerator is selected from the group consisting of benzophenone, p-methoxybenzophenone, acetophenone, m-chloroacetophenone, propiophenone, xanthone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl benzaldehyde, naphthoquinone, anthraquinone, 2,4,7-trinitro-9-fluorenone, 5-nitro-acenaphthene, p-nitrodiphenyl, p-nitroaniline and malachite green.
Claim 3
Dependent Claim
15 words
The laminated glass product according to claim 1, which is a laminated safety glass plate.
Claim 4
Dependent Claim
15 words
The laminated glass product according to claim 1, which is a laminated optical glass product.
Claim 5
Dependent Claim
79 words
The laminated glass product according to claim 1, wherein said photocurable composition comprises: from 25 to 75 wt. parts of said polyene; from 25 to 75 wt. parts of said polythiol; from 0.1 to 10 wt. parts of said organosilicone compound per 100 wt. parts of the total of said polyene and said polythiol; and from 0.1 to 5 wt. parts of said photocuring rate accelerator per 100 wt. parts of the total of said polyene and said polythiol.
Claim 6
Dependent Claim
319 words
A photocurable composition which comprises a polyene component, a polythiol component, an organosilicone compound and a photocuring rate accelerator wherein said polyene is a compound having the formula ##STR16## wherein m is an integer of 2 to 6; R represents a hydrogen atom, a C 1 -C 8 alkyl, a C 1 -C 3 alkoxy or phenyl group which can be substituted with a substituent of nitro, C 1 -C 8 alkyl or alkoxy group or a halogen atom; Y is --CH 2 ) n wherein n is 0 or an integer of 1 to 10, --CH 2 ) p wherein p is an integer of 1 to 10, --CH 2 ) q wherein q is an integer of 1 to 10 or ##STR17## and X is a polyvalent group which has a valency of m representing benzene, toluene, ethylene glycol, diethylene glycol, triethylene glycol, trimethylolpropane, phthalate, cyanurate, isocyanurate, trimellitate, ethane, N,N-piperazine, orthosilicate, phosphate, oxalate, terephthalate, diphenylterephthalate or methylenediamine group; said polythiol is a compound having the formula ##STR18## wherein Z is a group connecting m' members and is --CH 2 ) v , ##STR19## wherein v is an integer of 1 to 6, and w, x, y and z are respectively 0 or an integer of 2 to 6; m' is an integer of 2 to 4; n' and p' are respectively 0 or an integer of 1 to 3; said polythiol having an average molecular weight of 50 to 15,000; and said organosilicone compound is a compound having the formula ##STR20## wherein n" is 0 or an integer of 1 to 3; X represents chlorine atom or a C 1 -C 8 alkoxy or acetoxy group which can be substituted by chlorine atom, nitro group or a C 1 -C 2 alkoxy group; and Y represents vinyl group which can be substituted by chlorine atom, methoxy, ethoxy, propyloxy or acetoxy group; or acryloyl, methacryloyl or mercaptan group.
Claim 7
Dependent Claim
319 words
A photocurable composition which comprises a polyene component, a polythiol component, an organosilicone compound and a photocuring rate accelerator wherein said polyene is a compound having the formula ##STR16## wherein m is an integer of 2 to 6; R represents a hydrogen atom, a C 1 -C 8 alkyl, a C 1 -C 3 alkoxy or phenyl group which can be substituted with a substituent of nitro, C 1 -C 8 alkyl or alkoxy group or a halogen atom; Y is --CH 2 ) n wherein n is 0 or an integer of 1 to 10, --CH 2 ) p wherein p is an integer of 1 to 10, --CH 2 ) q wherein q is an integer of 1 to 10 or ##STR17## and X is a polyvalent group which has a valency of m representing benzene, toluene, ethylene glycol, diethylene glycol, triethylene glycol, trimethylolpropane, phthalate, cyanurate, isocyanurate, trimellitate, ethane, N,N-piperazine, orthosilicate, phosphate, oxalate, terephthalate, diphenylterephthalate or methylenediamine group; said polythiol is a compound having the formula ##STR18## wherein Z is a group connecting m' members and is --CH 2 ) v , ##STR19## wherein v is an integer of 1 to 6, and w, x, y and z are respectively 0 or an integer of 2 to 6; m' is an integer of 2 to 4; n' and p' are respectively 0 or an integer of 1 to 3; said polythiol having an average molecular weight of 50 to 15,000; and said organosilicone compound is a compound having the formula ##STR20## wherein n" is 0 or an integer of 1 to 3; X represents chlorine atom or a C 1 -C 8 alkoxy or acetoxy group which can be substituted by chlorine atom, nitro group or a C 1 -C 2 alkoxy group; and Y represents vinyl group which can be substituted by chlorine atom, methoxy, ethoxy, propyloxy or acetoxy group; or acryloyl, methacryloyl or mercaptan group.
Claim 8
Dependent Claim
75 words
A photocurable composition according to claim 5 which comprises from 25 to 75 wt. parts of said polyene; from 25 to 75 wt. parts of said polythiol; from 0.1 to 10 wt. parts of said organosilicone compound per 100 wt. parts of the total of said polyene and said polythiol; and from 0.1 to 5 wt. parts of said photocuring rate accelerator per 100 wt. parts of the total of said polyene and said polythiol.
Claim 9
Dependent Claim
49 words
A photocurable composition according to claim 6 wherein said photocuring rate accelerator is selected from the group consisting of benzophenone, p-methoxybenzophenone, acetophenone, m-chloroacetophenone, propiophenone, xanthone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl benzaldehyde, naphthoquinone, anthraquinone, 2,4,7-trinitro-9-fluorenone, 5-nitroacenaphthene, p-nitrodiphenyl, p-nitroaniline and malachite green.
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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) | 1984-06-08 | 1984-12-08 | 1985-06-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-06-08 | 1988-12-08 | 1989-06-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-06-08 | 1992-12-08 | 1993-06-09 | $7700.00 | Window Closed / Lapsed |