Macromonomers having reactive side groups
AssigneeMaxdem Incorporated
InventorsRobert R. Gagne, Matthew Louis Marrocco III, Mark Steven Trimmer, Neil H. Hendricks
Life of this patent
Estimating the term…
Abstract
Rigid-rod macromonomers, and methods for preparing such macromonomers, having a polyaromatic backbone, solubilizing side groups, and reactive side groups are provided. The macromonomers are chemically incorporated into polymer systems to provide stronger, stiffened polymers.
Claims37
A soluble rigid-rod macromonomer of the formula:
- ##STR29## wherein each A.sub.1, A.sub.2, A.sub.3, and A.sub.4, on each monomer unit, independently, is C or N;
- each G.sub.1, G.sub.2, G.sub.3, and G.sub.4, on each monomer unit, independently, is selected from the group consisting of H, solubilizing side groups, reactive side groups, and reactive solubilizing side groups, provided that (1) at least one monomer unit has at least one solubilizing side group and at least one monomer unit has at least one reactive side group, or (2) at least one monomer unit has at least one reactive solubilizing side group, wherein said solubilizing side groups and reactive solubilizing side groups provide said macromonomers with a solubility of at least 0.5% by weight in the solvent system from which they are formed, wherein said reactive side groups and reactive solubilizing side groups are selected from the group consisting of acetals from ethylvinyl ether, acetylenes, acid anhydrides, acrylamides, acrylates, alkyl aldehydes, primary amines, quaternary amines, aryl aldehydes, azides, benzocyclobutenes, biphenylenes, carbonates, carboxylic acids and their salts, carboxylic acid halides, cyanates, epoxides, fulvenes, heteroaryls, hydrazines, hydroxylamines, imines, isocyanates, ketals, maleimides, nadimides, phenols, phosphates, phosphonates, silicates, sulfonic acids and their salts, sulfonyl halides, tetrahydropyranyl ethers, urethanes, and vinyl ethers;
- and provided that when any of A.sub.1, A.sub.2, A.sub.3, and A.sub.4 is N, the corresponding G.sub.1, G.sub.2, G.sub.3, or G.sub.4 is nil;
- the macromonomer has a degree of polymerization, DP.sub.n, greater than 6;
- adjacent monomer units are oriented head-to-head, head-to-tail, or randomly;
- and the bonds between adjacent monomer units are para to each other.
A soluble rigid-rod macromonomer of the formula:
- ##STR31## wherein each G.sub.1, G.sub.2, G.sub.3, and G.sub.4, on each monomer unit, independently, is selected from the group consisting of H, solubilizing side groups, reactive side groups, and reactive solubilizing side groups, provided that (1) at least one monomer unit has at least one solubilizing side group and at least one monomer unit has at least one reactive side group, or (2) at least one monomer unit has at least one reactive solubilizing side group, wherein said solubilizing side groups and reactive solubilizing side groups provide said macromonomers with a solubility of at least 0.5% by weight in the solvent system from which they are formed, wherein said reactive side groups and reactive solubilizing side groups are selected from the group consisting of acetals from ethylvinyl ether, acetylenes, acid anhydrides, acrylamides, acrylates, alkyl aldehydes, primary amines, quaternary amines, aryl aldehydes, azides, benzocyclobutenes, biphenylenes, carbonates, carboxylic acids and their salts, carboxylic acid halides, cyanates, epoxides, fulvenes, heteroaryls, hydrazines, hydroxylamines, imines, isocyanates, ketals, maleimides, nadimides, phenols, phosphates, phosphonates, silicates, sulfonic acids and their salts, sulfonyl halides, tetrahydropyranyl ethers, urethanes, and vinyl ethers;
- the macromonomer has a degree of polymerization, DP.sub.n, greater than 6;
- adjacent monomer units are oriented head-to-head, head-to-tail, or randomly;
- and the bonds between adjacent monomer units are para to each other.
A soluble rigid-rod macromonomer of the formula:
- ##STR32## wherein each A.sub.1, A.sub.2, A.sub.3, and A.sub.4, on each monomer unit, independently, is C or N;
- each G.sub.1, G.sub.2, G.sub.3, and G.sub.4, on each monomer unit, independently, is selected from the group consisting of H, solubilizing side groups, reactive side groups, and reactive solubilizing side groups, provided that (1) at least one monomer unit has at least one solubilizing side group and at least one monomer unit has at least one reactive side group, or (2) at least one monomer unit has at least one reactive solubilizing side group, wherein said solubilizing side groups and reactive solubilizing side groups provide said macromonomers with a solubility of at least 0.5% by weight in the solvent system from which they are formed, wherein said reactive side groups and reactive solubilizing side groups are olefins selected from the group consisting of:
- ##STR33## wherein Y is --CH.dbd.CH.sub.2, R.sub.1 -R.sub.4 may be independently selected from hydrogen, alkyl, aryl, alkaryl, aralkyl, alkylketone, arylketone, alkylether, or arylether, and Z is a difunctional group selected from nil, phenyleneoxy, ketophenylene, phenylenesulfone, --O--, --NH--, keto, --SO.sub.2 --, aryl, alkyl, alkaryl, or aralkyl, wherein two adjacent Rs can be taken together as bridging groups selected from --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CO--, and provided that when any of A.sub.1, A.sub.2, A.sub.3, and A.sub.4 is N, the corresponding G.sub.1, G.sub.2, G.sub.3, or G.sub.4 is nil, the macromonomer has a degree of polymerization, DP.sub.n, greater than 6, adjacent monomer units are oriented head-to-head, head-to-tail, or randomly, and the bonds between adjacent monomer units are para to each other.
A soluble rigid-rod macromonomer of the formula:
- ##STR34## wherein each A.sub.1, A.sub.2, A.sub.3, and A.sub.4, on each monomer unit, independently, is C or N;
- each G.sub.1, G.sub.2, G.sub.3, and G.sub.4 on each monomer unit, independently, is selected from the group consisting of H, solubilizing side groups, reactive side groups, and reactive solubilizing side groups, provided that (1) at least one monomer unit has at least one solubilizing side group and at least one monomer unit has at least one reactive side group, or (2) at least one monomer unit has at least one reactive solubilizing side group, wherein said solubilizing side groups and reactive solubilizing side groups provide said macromonomers with a solubility of at least 0.5% by weight in the solvent system from which they are formed, wherein said reactive side groups and reactive solubilizing side groups are halides selected from the group consisting of:
- ##STR35## wherein Y is halogen and wherein R.sub.1 -R.sub.4 may be independently selected from hydrogen, alkyl, aryl, alkaryl, aralkyl, alkylketone, arylketone, alkylether, or arylether, and Z is a difunctional group selected from phenyleneoxy, ketophenylene, phenylenesulfone, --O--, --NH--, keto, --SO.sub.2 --, aryl, alkyl, alkaryl, or aralkyl, wherein two adjacent Rs can be taken together as bridging groups selected from --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CO--, and provided that when any of A.sub.1, A.sub.2, A.sub.3, and A.sub.4 is N, the corresponding G.sub.1, G.sub.2 G,.sub.3 or G .sub.4 is nil, the macromonomer has a degree of polymerization, DP.sub.n, greater than 6, adjacent monomer units are oriented head-to-head, head-to-tail, or randomly, and the bonds between adjacent monomer units are para to each other.
A soluble rigid-rod macromonomer of the formula:
- ##STR36## wherein each A.sub.1, A.sub.2, A.sub.3, and A.sub.4, on each monomer unit, independently, is C or N;
- each G.sub.1, G.sub.2, G.sub.3, and G.sub.4, on each monomer unit, independently, is selected from the group consisting of H, solubilizing side groups, reactive side groups, and reactive solubilizing side groups, provided that (1) at least one monomer unit has at least one solubilizing side group and at least one monomer unit has at least one reactive side group, or (2) at least one monomer unit has at least one reactive solubilizing side group, wherein said solubilizing side groups and reactive solubilizing side groups provide said macromonomers with a solubility of at least 0.5% by weight in the solvent system from which they are formed, wherein said reactive side groups and reactive solubilizing side groups are bromine groups connected directly to the macromonomer backbone, and provided that when any of A.sub.1, A.sub.2, A.sub.3, and A.sub.4 is N, the corresponding G.sub.1, G.sub.2, G.sub.3, or G.sub.4 is nil, the macromonomer has a degree of polymerization, DP.sub.n, greater than 6, adjacent monomer units are oriented head-to-head, head-to-tail, or randomly, and the bonds between adjacent monomer units are para to each other.
A soluble rigid-rod macromonomer of the formula:
- ##STR37## wherein each A.sub.1, A.sub.2, A.sub.3, and A.sub.4, on each monomer unit, independently, is C or N;
- each G.sub.1, G.sub.2 G.sub.3 and G.sub.4 on each monomer unit, independently, is selected from the group consisting of H, solubilizing side groups, reactive side groups, and reactive solubilizing side groups, provided that (1) at least one monomer unit has at least one solubilizing side group and at least one monomer unit has at least one reactive side group, or (2) at least one monomer unit has at least one reactive solubilizing side group, wherein said solubilizing side groups and reactive solubilizing side groups provide said macromonomers with a solubility of at least 0.5% by weight in the solvent system from which they are formed, wherein at least one of the monomer units incorporates at least one solubilizing group comprising a benzoyl group and at least one of the monomer units incorporates at least one reactive side group comprising a carbomethoxy group, and provided that when any of A.sub.1, A.sub.2, A.sub.3, and A.sub.4 is N, the corresponding G.sub.1, G.sub.2, G.sub.3, or G.sub.4 is nil, the macromonomer has a degree of polymerization, DP.sub.n, greater than 6, adjacent monomer units are oriented head-to-head, head-to-tail, or randomly, and the bonds between adjacent monomer units are para to each other.
Dependencies are inferred from the claim text.