Control agents for living-type free radical polymerization, methods of polymerizing and polymers with same
AssigneeSymyx Technologies, Inc.
InventorsDominique Charmot, Han Ting Chang
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Abstract
Control agents that have a nitrogen-nitrogen bond covalently bonded to a thiocarbonyl moiety are provided for living-type free radical polymerization of a wide variety of monomers. These control agents provide superior properties for control of the polymerization and/or the properties of the polymers obtained and/or the monomers that may be polymerized. In some embodiments, a bulky group is pendant off the activated thiocarbonyl portion of the control agents. Multifunctional control agents provide the opportunity for a variety of structurally unique polymers, including block copolymers, stars and hyper-branched polymers.
Claims36
A method of free radical polymerization comprising (1) forming a mixture of one or more monomers, at least one free radical source and a control agent and (2) subjecting said mixture to polymerization conditions, wherein said control agent contains at least one N-N bond covalently bonded to a thiocarbonyl group.
A method of method of free radical polymerization comprising (1) forming a mixture of one or more monomers, at least one free radical source and a multi-functional control agent and (2) subjecting said mixture to polymerization conditions, wherein said control agent contains at least one N-N bond covalently bonded to a thiocarbonyl moiety.
A compound characterized by the formula:
- 41
- wherein R1 is selected from the group consisting of hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, and substituted heteroatom-containing hydrocarbyl, and combinations thereof, with the proviso that R1 is not methyl;
- R2 and R3 are each independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, and substituted heteroatom-containing hydrocarbyl, and combinations thereof, and
- R4 is selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, and substituted heteroatom-containing hydrocarbyl, and combinations thereof;
- and optionally, R4 combines with R2 and/or R3 to form a ring structure, with said ring having from 3 to 50 non-hydrogen atoms.
A compound characterized by the formula:
- 42
- wherein R1 is selected from the group consisting of hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, and substituted heteroatom-containing hydrocarbyl, and combinations thereof;
- R2 and R3 are each independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, and substituted heteroatom-containing hydrocarbyl, and combinations thereof, and
- R4 is selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, and substituted heteroatom-containing hydrocarbyl, and combinations thereof;
- and optionally, R4 combines with R2 and/or R3 to form a ring structure, with said ring having from 3 to 50 non-hydrogen atoms.
Dependencies are inferred from the claim text.