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US 6,187,836 B1Granted
Compositions featuring cationically active and free radically active functional groups, and methods for polymerizing such compositions
Assignee3M Innovative Properties Company
InventorsJoel D. Oxman, Matthew C. Trom, Dwight W. Jacobs
Life of this patent
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Abstract
Photopolymerizable compositions that include free radically active and cationically active functional groups, and methods for polymerizing such compositions, in which the onset of cationic polymerization is controllably delayed to extend the time between formation of a moldable gel and formation of a hardened solid.
Claims59
A photopolymerizable dental composition comprising:
- (a) a cationically active functional group;
- (b) a free radically active functional group;
- and
- (c) a photoinitiation system capable of initiating, at a reaction temperature less than about 40° C., free radical polymerization of said free radically active functional group after a finite induction period T1 and cationic polymerization of said cationically active functional group after a finite induction period T3, where T3 is greater than T1,
- said photoinitiation system comprising:
- (i) a source of species capable of initiating free radical polymerization of said free radically active functional group and cationic polymerization of said cationically active functional group;
- and
- (ii) a cationic polymerization modifier,
- wherein in the absence of said modifier, cationic polymerization of said cationically active functional group is initiated under the same irradiation conditions at the end of a finite induction period T2, where T2 is less than T3.
6 more elements
A photopolymerizable composition comprising:
- (a) a cationically active functional group;
- (b) a free radically active functional group;
- and
- (c) a photoinitiation system capable of initiating, at a reaction temperature less than about 40° C., free radical polymerization of said free radically active functional group after a finite induction period T1 and cationic polymerization of said cationically active functional group after a finite induction period T3, where T3 is greater than T1,
- said photoinitiation system comprising:
- (i) a source of species capable of initiating free radical polymerization of said free radically active functional group and cationic polymerization of said cationically active functional group;
- and
- (ii) a cationic polymerization modifier,
- wherein in the absence of said modifier, cationic polymerization of said cationically active functional group is initiated under the same irradiation conditions at the end of a finite induction period T2, where T2 is less than T3.
6 more elements
A method of polymerizing a photopolymerizable dental composition, said method comprising applying said composition to a surface and exposing said composition to a source of actinic radiation at a reaction temperature less than 40° C.,
- said photopolymerizable composition comprising:
- (a) a cationically active functional group;
- (b) a free radically active functional group;
- and
- (c) a photoinitiation system capable of initiating, at said reaction temperature, free radical polymerization of said free radically active functional group after a finite induction period T1 and cationic polymerization of said cationically active functional group after a finite induction period T3, where T3 is greater than T1,
- said photoinitiation system comprising:
- (i) a source of species capable of initiating free radical polymerization of said free radically active functional group and cationic polymerization of said cationically active functional group;
- and
- (ii) a cationic polymerization modifier,
- wherein in the absence of said modifier, cationic polymerization of said cationically active functional group is initiated under the same irradiation conditions at the end of a finite induction period T2, where T2 is less than T3.
7 more elements
A method of polymerizing a composition, said method comprising exposing a photopolymerizable composition to a source of actinic radiation at a reaction temperature,
- said photopolymerizable composition comprising:
- (a) a cationically active functional group;
- (b) a free radically active functional group;
- and
- (c) a photoinitiation system capable of initiating, at said reaction temperature, free radical polymerization of said free radically active functional group after a finite induction period T1 and cationic polymerization of said cationically active functional group after a finite induction period T3, where T3 is greater than T1,
- said photoinitiation system comprising:
- (i) a source of species capable of initiating free radical polymerization of said free radically active functional group and cationic polymerization of said cationically active functional group;
- and
- (ii) a cationic polymerization modifier,
- wherein in the absence of said modifier, cationic polymerization of said cationically active functional group is initiated under the same irradiation conditions at the end of a finite induction period T2, where T2 is less than T3.
7 more elements
A method of preparing a polymerized dental composition, said method comprising:
- (a) providing a polymerizable dental composition comprising:
- (i) a cationically active functional group;
- (ii) a free radically active functional group;
- (iii) a first initiation system capable of initiating free radical polymerization of said free radically active functional group at a first reaction temperature less than 40° C,;
- and
- (iv) a second initiation system different from said first initiation system that is capable of initiating photo-induced cationic polymerization of said cationically active functional group at a second reaction temperature less than 40° C.;
- (b) applying said composition to a surface,
- (c) inducing polymerization of said free radically active functional group at said first reaction temperature;
- and
- (d) thereafter exposing said composition to actinic radiation at said second reaction temperature to cause polymerization of said cationically active functional group.
7 more elements
A method of delaying the onset of cationic polymerization in a polymerizable hybrid composition, said method comprising the steps of:
- (a) providing a photopolymerizable composition comprising:
- (i) a cationically active functional group;
- (ii) a free radically active functional group;
- and
- (iii) a photoinitiation system comprising:
- (1) a source of species capable of initiating free radical polymerization of said free radically active functional group and cationic polymerization of said cationically active functional group;
- and
- (2) a cationic polymerization modifier;
- and
- (b) exposing said photopolymerizable composition to a source of actinic radiation at a reaction temperature;
- wherein said photoinitiation system is capable of initiating at said reaction temperature free radical polymerization of said free radically active functional group after a finite induction period T1 and cationic polymerization of said cationically active functional group after a finite induction period T3, where T3 is greater than T1;
- and
- further wherein in the absence of said cationic polymerization modifier, cationic polymerization of said cationically active functional group is initiated under the same irradiation conditions at the end of a finite induction period T2, where T2 is less than T3.
10 more elements
Dependencies are inferred from the claim text.