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US4391963A
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Organopolysiloxane photosensitizers and methods for their preparation
Assignee: DuPont Toray Specialty Materials KK
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Filing: 1982-05-27
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Granted: 1983-07-05
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Expires: 2002-05-27
Abstract
Abstract Novel photosensitizers are disclosed which are particularly useful in photopolymerizable organopolysiloxane and silicone resins. The photosensitizers are themselves organopolysiloxanes which contain at least one silicon-bonded benzoin-containing radical. Synthesis methods are disclosed for preparing these photosensitizers which employ, as starting materials, an alkenyl-substituted benzoin and a silicon compound containing at least one silicon-bonded hydrogen atom.
Inventors
- 👤 Akihiko Shirahata
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 23:29
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/075; G03F7/0757; C; C08; C08G; C08G77/00; C08G77/04; C08G77/14; C08G77/38; C08L; C08L83/00; C08L83/04; C08G77/12; C08G77/18; C08G77/20; C08G77/22; C08G77/24; C08G77/26; C08G77/28; C08G77/70; Y; Y10; Y10S; Y10S522/00; Y10S522/904
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
180 words
An organopolysiloxane photosensitizer comprising an average of at least two siloxane units, of which at least an average of one siloxane unit per organopolysiloxane molecule has the formula Q a R b 5 SiO.sub.(4-a-b)/2, wherein Q denotes a benzoin-containing group having the formula ##STR17## R 1 and R 2 each denote, independently, a hydrogen atom, a halogen atom, a monovalent hydrocarbon group having from 1 to 10 carbon atoms, an alkoxy group, a thioalkoxy group, an amino group or a dialkylamino group; R 3 denotes a hydrogen atom or a monovalent hydrocarbon group having from 1 to 10 carbon atoms; R 4 denotes a divalent hydrocarbon group having from 2 to 10 carbon atoms; R 5 denotes a monovalent hydrocarbon group having from 1 to 10 carbon atoms or a halogenated monovalent hydrocarbon group; m is an integer of from 1 to 5, n is an integer of from 1 to 5, a is an integer of from 1 to 3, b is an integer of from 0 to 2 and a+b is an integer of from 1 to 3.
Claim 2
Dependent Claim
180 words
An organopolysiloxane photosensitizer comprising an average of at least two siloxane units, of which at least an average of one siloxane unit per organopolysiloxane molecule has the formula Q a R b 5 SiO.sub.(4-a-b)/2, wherein Q denotes a benzoin-containing group having the formula ##STR17## R 1 and R 2 each denote, independently, a hydrogen atom, a halogen atom, a monovalent hydrocarbon group having from 1 to 10 carbon atoms, an alkoxy group, a thioalkoxy group, an amino group or a dialkylamino group; R 3 denotes a hydrogen atom or a monovalent hydrocarbon group having from 1 to 10 carbon atoms; R 4 denotes a divalent hydrocarbon group having from 2 to 10 carbon atoms; R 5 denotes a monovalent hydrocarbon group having from 1 to 10 carbon atoms or a halogenated monovalent hydrocarbon group; m is an integer of from 1 to 5, n is an integer of from 1 to 5, a is an integer of from 1 to 3, b is an integer of from 0 to 2 and a+b is an integer of from 1 to 3.
Claim 3
Dependent Claim
41 words
A composition according to claim 1 wherein any siloxane unit in the organopolysiloxane photosensitizer molecules not bearing a Q group has the formula R c 5 H d SiO.sub.(4-c-d)/2 wherein c, d and c+d are integers of from 0 to 3.
Claim 4
Dependent Claim
39 words
A composition according to claim 2 wherein the average number of Q groups in the organopolysiloxane molecule is equal to from 0.2% to 50% of the total number of Q groups plus R 5 groups in the organopolysiloxane molecule.
Claim 5
Dependent Claim
24 words
A composition according to claim 1, 2 or 3 wherein each R 5 denotes a methyl group and a has a value of 1.
Claim 6
Dependent Claim
30 words
A composition according to claim 4 wherein the organopolysiloxane photosensitizer has the formula ##STR18## wherein x, y and z denote integers whose sum has a value of less than 1000.
Claim 7
Independent Claim
256 words
A method for preparing an organopolysiloxane photosensitizer comprising an average of at least two siloxane units, of which at least an average of one siloxane unit per organopolysiloxane molecule has the formula Q a R b 5 SiO.sub.(4-a-b)/2, said method comprising reacting, by a hydrosilylation reaction, an alkenyl-substituted benzoin reactant having the formula ##STR19## and an organohydrogenpolysiloxane reactant containing at least than two siloxane units and at least one silicon-bonded hydrogen atom per molecule, wherein Q denotes a benzoin-containing group having the formula ##STR20## at each occurrence R 1 and R 2 denote, independently, a hydrogen atom, a halogen atom, a monovalent hydrocarbon group having from 1 to 10 carbon atoms, an alkoxy group, a thioalkoxy group, an amino group or a dialkylamino group; R 3 denotes a hydrogen atom or a monovalent hydrocarbon group having from 1 to 10 carbon atoms; R 4 denotes a divalent hydrocarbon group having from 2 to 10 carbon atoms; R 5 denotes a monovalent hydrocarbon group having from 1 to 10 carbon atoms or a halogenated monovalent hydrocarbon group; R 6 denotes an aliphatically unsaturated monovalent hydrocarbon group having the same number of carbon atoms as the R 4 group; m is an integer of from 1 to 5, n is an integer of from 1 to 5, a is an integer of from 1 to 3, b is an integer of from 0 to 2 and a+b is an integer of from 1 to 3 whereby the R 6 group becomes the R 4 group during said reaction.
Claim 8
Independent Claim
256 words
A method for preparing an organopolysiloxane photosensitizer comprising an average of at least two siloxane units, of which at least an average of one siloxane unit per organopolysiloxane molecule has the formula Q a R b 5 SiO.sub.(4-a-b)/2, said method comprising reacting, by a hydrosilylation reaction, an alkenyl-substituted benzoin reactant having the formula ##STR19## and an organohydrogenpolysiloxane reactant containing at least than two siloxane units and at least one silicon-bonded hydrogen atom per molecule, wherein Q denotes a benzoin-containing group having the formula ##STR20## at each occurrence R 1 and R 2 denote, independently, a hydrogen atom, a halogen atom, a monovalent hydrocarbon group having from 1 to 10 carbon atoms, an alkoxy group, a thioalkoxy group, an amino group or a dialkylamino group; R 3 denotes a hydrogen atom or a monovalent hydrocarbon group having from 1 to 10 carbon atoms; R 4 denotes a divalent hydrocarbon group having from 2 to 10 carbon atoms; R 5 denotes a monovalent hydrocarbon group having from 1 to 10 carbon atoms or a halogenated monovalent hydrocarbon group; R 6 denotes an aliphatically unsaturated monovalent hydrocarbon group having the same number of carbon atoms as the R 4 group; m is an integer of from 1 to 5, n is an integer of from 1 to 5, a is an integer of from 1 to 3, b is an integer of from 0 to 2 and a+b is an integer of from 1 to 3 whereby the R 6 group becomes the R 4 group during said reaction.
Claim 9
Dependent Claim
34 words
A method according to claim 6 wherein the organohydrogenpolysiloxane consists of siloxane units having the formula R c 5 H d SiO.sub.(4-c-d)/2 wherein c, d and c+d are integers of from 0 to 3.
Claim 10
Dependent Claim
14 words
A method according to claim 7 wherein each R 5 denotes a methyl group.
Claim 11
Dependent Claim
45 words
A method according to claim 6, 7 or 8 wherein the organohydrogenpolysiloxane has the formula R 3 5 SiO(R 2 5 SiO) x (R 5 HSiO) w SiR 3 5 wherein x and w denote integers whose sum has a value of less than 1000.
Claim 12
Dependent Claim
15 words
A method according to claim 9 wherein the alkenyl-substituted benzoin reactant has the formula ##STR21##
Claim 13
Independent Claim
308 words
A method for preparing an organopolysiloxane photosensitizer comprising an average of at least two siloxane units, of which an average of at least one siloxane unit per organopolysiloxane molecule has the formula Q a R b 5 SiO.sub.(4-a-b)/2, said method comprising (A) reacting, by a hydrosilylation reaction to form an adduct, an alkenyl-substituted benzoin reactant having the formula ##STR22## and a silane bearing at least one silicon-bonded hydrogen atom and at least one silicon-bonded hydrolyzable group or a siloxane bearing at least two siloxane units and at least one silicon-bonded hydrogen atom; and (B) polymerizing the adduct or copolymerizing the adduct with another silane bearing at least one silicon-bonded hydrolyzable radical or with a siloxane, both being free of Q groups, to provide the organopolysiloxane photosensitizer, wherein Q denotes a benzoin-containing group having the formula ##STR23## at each occurrence R 1 and R 2 denote, independently, a hydrogen atom, a halogen atom, a monovalent hydrocarbon group having from 1 to 10 carbon atoms, an alkoxy group, a thioalkoxy group, an amino group or a dialkylamino group; R 3 denotes a hydrogen atom or a monovalent hydrocarbon group having from 1 to 10 carbon atoms; R 4 denotes a divalent hydrocarbon group having from 2 to 10 carbon atoms; R 5 denotes a monovalent hydrocarbon group having from 1 to 10 carbon atoms or a halogenated monovalent hydrocarbon group; R 6 denotes an aliphatically unsaturated monovalent hydrocarbon group having the same number of carbon atoms as the R 4 group; m is an integer of from 1 to 5, n is an integer of from 1 to 5, a is an integer of from 1 to 3, b is an integer of from 0 to 2 and a+b is an integer of from 1 to 3; the R 6 group becoming the R 4 group during said hydrosilylation reaction.
Claim 14
Independent Claim
308 words
A method for preparing an organopolysiloxane photosensitizer comprising an average of at least two siloxane units, of which an average of at least one siloxane unit per organopolysiloxane molecule has the formula Q a R b 5 SiO.sub.(4-a-b)/2, said method comprising (A) reacting, by a hydrosilylation reaction to form an adduct, an alkenyl-substituted benzoin reactant having the formula ##STR22## and a silane bearing at least one silicon-bonded hydrogen atom and at least one silicon-bonded hydrolyzable group or a siloxane bearing at least two siloxane units and at least one silicon-bonded hydrogen atom; and (B) polymerizing the adduct or copolymerizing the adduct with another silane bearing at least one silicon-bonded hydrolyzable radical or with a siloxane, both being free of Q groups, to provide the organopolysiloxane photosensitizer, wherein Q denotes a benzoin-containing group having the formula ##STR23## at each occurrence R 1 and R 2 denote, independently, a hydrogen atom, a halogen atom, a monovalent hydrocarbon group having from 1 to 10 carbon atoms, an alkoxy group, a thioalkoxy group, an amino group or a dialkylamino group; R 3 denotes a hydrogen atom or a monovalent hydrocarbon group having from 1 to 10 carbon atoms; R 4 denotes a divalent hydrocarbon group having from 2 to 10 carbon atoms; R 5 denotes a monovalent hydrocarbon group having from 1 to 10 carbon atoms or a halogenated monovalent hydrocarbon group; R 6 denotes an aliphatically unsaturated monovalent hydrocarbon group having the same number of carbon atoms as the R 4 group; m is an integer of from 1 to 5, n is an integer of from 1 to 5, a is an integer of from 1 to 3, b is an integer of from 0 to 2 and a+b is an integer of from 1 to 3; the R 6 group becoming the R 4 group during said hydrosilylation reaction.
Claim 15
Dependent Claim
47 words
A method according to claim 11 wherein the siloxane bearing at least two siloxane units and at least one silicon-bonded hydrogen atom consists of siloxane units having the formula R c 5 H d SiO.sub.(4-c-d)/2 wherein c, d and c+d are integers of from 0 to 3.
Claim 16
Dependent Claim
32 words
A method according to claim 12 wherein the siloxane bearing at least two siloxane units and at least one silicon-bonded hydrogen atom is tetramethyltetrahydrocyclotetrasiloxane having the formula (CH 3 HSiO) 4 .
Claim 17
Dependent Claim
54 words
A method according to claim 11 wherein the silane bearing at least one silicon-bonded hydrogen atom and at least one silicon-bonded hydrolyzable group has the formula R e 5 HSiZ 3-e wherein e is an integer of from 0 to 2 and Z denotes a chlorine atom, an alkoxy group or an acyloxy group.
Claim 18
Dependent Claim
20 words
A method according to claim 14 wherein R 5 denotes a methyl radical and e has a value of 1.
Claim 19
Dependent Claim
20 words
A method according to claim 11, 12, 13, 14 or 15 wherein the alkenyl-substituted benzoin reactant has the formula ##STR24##
References Cited (Backward Citations)
US4273907A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-07-04 | 1987-01-03 | 1987-07-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-07-04 | 1991-01-03 | 1991-07-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-07-04 | 1995-01-03 | 1995-07-05 | $7700.00 | Window Closed / Lapsed |