Accelerators for cationic polymerization catalyzed by iron-based catalysts
Assignee3M Innovative Properties Company
InventorsWayne S. Mahoney, Michael C. Palazzotto
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Abstract
Accelerators that can be useful for an energy polymerizable composition comprising a cationically curable material; energy polymerizable compositions comprising at least one cationically curable material and an initiation system therefor, the initiation system comprising at least one organometallic complex salt and at least one accelerator; and a method for curing the compositions. The cured compositions can provide useful articles. The invention also provides compositions of matter comprising an organometallic complex salt and at least one compound selected from the Class 1 through Class 4 compounds disclosed herein.
Claims26
A method of using an accelerator to increase the rate, or reduce the temperature, of cure of an energy-polymerizable composition comprising the step of forming a composition by combining an accelerator, a cationically curable material and at least one salt of an organometallic complex cation, wherein said cation contains at least one carbon atom bonded to a transition metal atom, and wherein said accelerator is a compound selected from the group consisting of classes 1, 2, 3,
- wherein
- class 1 compounds are represented by Formula III:
- wherein each R1, independently, is hydrogen, chloro, iodo, bromo, fluoro, hydroxy, cyano, nitro, nitroso, carboxyl, formyl, acetyl, benzoyl, trialkylsilyl, trialkoxysilyl, a substituted or unsubstituted alkyl, alkenyl, alkynyl, and alkoxy groups containing up to 30 carbon atoms, one to four substituted or unsubstituted aromatic rings wherein two to four rings are fused or unfused, or two R1s taken together form at least one ring which is saturated or unsaturated and the ring is substituted or unsubstituted;
- class 2 compounds are represented by Formula IV:
- wherein each R2 is the same or different as the other R2s and is the same materials as those described for R1 in the Class 1 accelerators;
- or two R2s are replaced with a double bonded oxygen to form a carbonyl group;
- and
- class 3 compounds are represented by Formula V:
- wherein each R1, independently, has the same definition as in Formula III and R3 is selected from C1 to C10 substituted or unsubstituted alkyl groups, or groups of one to four substituted or unsubstituted aromatic rings wherein two to four rings are fused or unfused.
A composition of matter comprising
- (1) at least one salt of an organometallic complex cation, wherein said cation contains at least one carbon atom bonded to a transition metal atom, and
- (2) one or more accelerators that consist essentially,of a compound selected from the group consisting of classes 1, 2, 3
- wherein
- class 1 compounds are represented by Formula III:
- wherein one, two, four or five R1s are hydroxy and each remaining R1, independently, is hydrogen, chloro, iodo, bromo, fluoro, cyano, nitro, nitroso, carboxyl, formyl, acetyl, benzoyl, trialkylsilyl, and trialkoxysilyl, a substituted and unsubstituted alkyl, alkenyl, alkynyl, and alkoxy groups containing up to 30 carbon atoms, one to four substituted or unsubstituted aromatic rings wherein two to four rings are fused or unfused, or two R1s taken together form at least one ring which is saturated or unsaturated and the ring is substituted or unsubstituted;
- class 2 compounds are represented by Formula IV:
- wherein each R2 is the same or different as the other R2s and is the same materials as those described for R1 in the Class 1 accelerators;
- or two R2s are replaced with a double bonded oxygen to form a carbonyl group;
- and
- class 3 compounds are represented by Formula V:
- wherein each R1, independently, has the same definition as in Formula III and R3 is selected from C1 to C10 substituted or unsubstituted alkyl groups, or groups of one to four substituted or unsubstituted aromatic rings wherein two to four rings are fused or unfused, and adding sufficient energy in the form of at least one of heat, radiation, and light, in any combination or order, to cure said cationically curable material.
An energy polymerizable composition comprising
- a) at least one cationically curable material,
- b) a two-component initiator system comprising
- (1) at least one salt of an organometallic complex cation, wherein said cation contains at least one carbon atom bonded to a transition metal atom, and
- (2) one or more accelerators selected from the group consisting of classes 1, 2, 3
- wherein
- class 1 compounds are represented by Formula III:
- wherein each R1, independently, is hydrogen, chloro, iodo, bromo, hydroxy, fluoro, cyano, nitro, nitroso, carboxyl, formyl, acetyl, benzoyl, trialkylsilyl, and trialkoxysilyl, a substituted and unsubstituted alkyl, alkenyl, alkynyl, and alkoxy groups containing up to 30 carbon atoms, one to four substituted or unsubstituted aromatic rings wherein two to four rings are fused or unfused, or two R1s taken together form at least one ring which is saturated or unsaturated and the ring is substituted or unsubstituted;
- class 2 compounds are represented by Formula IV:
- wherein each R2 is the same or different as the other R2s and is the sarne materials as those described for R1 in the Class 1 accelerators;
- or two R2s are replaced with a double bonded oxygen to form a carbonyl group;
- and
- class 3 compounds are represented by Formula V:
- wherein each R1, independently, has the same definition as in Formula III and R3 is selected from C1 to C10 substituted or unsubstituted alkyl groups, or groups of one to four substituted or unsubstituted aromatic rings wherein two to four rings are fused or unfused.
Dependencies are inferred from the claim text.