US 10,889,687 B2
Polymerizable compositions, polymerized compositions, and methods of making and using the same
Robert S. Clough, St. Paul, MN (US); Susan E. DeMoss, Stillwater, MN (US); and Michael A. Kropp, Cottage Grove, MN (US)
Assigned to 3M Innovative Properties Company, St. Paul, MN (US)
Appl. No. 15/756,283
Filed by 3M INNOVATIVE PROPERTIES COMPANY, St. Paul, MN (US)
PCT Filed Sep. 9, 2016, PCT No. PCT/US2016/050895
§ 371(c)(1), (2) Date Feb. 28, 2018,
PCT Pub. No. WO2017/044704, PCT Pub. Date Mar. 16, 2017.
Claims priority of provisional application 62/216,711, filed on Sep. 10, 2015.
Prior Publication US 2018/0237590 A1, Aug. 23, 2018
This patent is subject to a terminal disclaimer.
Int. Cl. C08G 75/12 (2016.01); C08G 75/045 (2016.01)
CPC C08G 75/12 (2013.01) [C08G 75/045 (2013.01)] 13 Claims
 
1. A polymerizable composition comprising:
an organoborane-base complex that is a complex of an organoborane and a base,
wherein the organoborane is represented by the formula B(R1)(R2)(R3) wherein:
R1 represents an alkyl group having from 1 to 10 carbon atoms; and R2 and R3 independently represent: alkyl groups having 1 to 10 carbon atoms; cycloalkyl groups having 3 to 10 carbon atoms; aryl groups having 6 to 12 carbon atoms; or aryl groups substituted with alkyl groups having 1 to 10 carbon atoms or cycloalkyl groups having 3 to 10 carbon atoms, or any two of R1, R2, and R3 taken together form a divalent alkylene group having from 3 to 7 carbon atoms, and
wherein the base is a complexing agent selected from a compound having one or more functional groups selected from the group consisting of amine groups, amidine groups, hydroxide groups, alkoxide groups, and combinations thereof;
a decomplexing agent that at least partially liberates the organoborane from the organoborane-base complex;
a polymerizable thiol-containing component comprising at least one polymerizable thiol-containing compound having a plurality of thiol groups in which the sulfur atom of the thiol group is covalently bonded to carbon;
a hydroperoxide; and
a polymerizable ethylenically-unsaturated component comprising at least one polymerizable ethylenically-unsaturated compound having a plurality of ethylenically-unsaturated groups;
wherein the combined amounts of the thiol-containing and ethylenically-unsaturated compounds total at least 50 percent by weight of all polymerizable material in the polymerizable composition.