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US 12,617,751 B2Granted
Visible light active biomass derived photoinitiators
AssigneeBowling Green State University
InventorsJayaraman Sivaguru, Ravichandranath Singathi, Sruthy Baburaj
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Abstract
Biomass derived benzoin derivatives, and methods of making and using the same, are described. Benzoin derivatives may be used as visible light photoinitiators.
Claims20
A composition comprising Formula Bz-1:
- wherein:
- dashed lines indicate optional bonds;
- X is O, S, NH, Ge, NC(O)—O—RC, N—O—C(O)RC, or NO—RC, wherein RC is alkyl, aryl, or heteroaryl;
- each of A and B is a phenyl ring;
- Z is OH or H;
- Y is OH, alkoxy, halo, SH, S-alkyl, carboxy, aryloxy, or a hetero-atom;
- and
- substituents RA1 to RA5 and RB1 to RB5 are any combination of H, alkyl, alkene, alkynes, aryl, heterocyclic, alkenyl halides, unsaturated enones, unsaturated ketones, unsaturated amides, unsaturated alcohols, unsaturated amines, unsaturated thiols, phosphonates, carboxylates, sulfonates, nitriles, thioethers, thioketones, azides, sulfides, disulfides, ethers, epoxides, nitrates, nitrites, nitro compounds, nitroso compounds, alkyl ketoesters, acylgermanes, metallocenes, organosilanes, oximes, imides, cyanates, isocyanates, thiocyanates, isothiocyanates, sulfoxides, sulfones, sulfites, phosphites, thial, phosphines, and aldehydes;
- provided that one of A or B has two methoxy substituents.
6 more elements
A composition comprising Formula Bz-2 or Formula Bz-3:
- wherein:
- dashed lines indicate optional bonds;
- X is O, S, NH, Ge, NC(O)—O—RC, N—O—C(O)RC, or NO—RC, wherein RC is alkyl, aryl, or heteroaryl;
- each of A and B is a phenyl ring;
- Z is OH or H;
- Y is OH, alkoxy, halo, SH, S-alkyl, carboxy, aryloxy, or a hetero-atom;
- substituents RA1 to RA5 and RB1 to RB5 are any combination of H, alkyl, alkene, alkynes, aryl, heterocyclic, alkenyl halides, unsaturated enones, unsaturated ketones, unsaturated amides, unsaturated alcohols, unsaturated amines, unsaturated thiols, phosphonates, carboxylates, sulfonates, nitriles, thioethers, thioketones, azides, sulfides, disulfides, ethers, epoxides, nitrates, nitrites, nitro compounds, nitroso compounds, alkyl ketoesters, acylgermanes, metallocenes, organosilanes, oximes, imides, cyanates, isocyanates, thiocyanates, isothiocyanates, sulfoxides, sulfones, sulfites, phosphites, thial, phosphines, and aldehydes;
- and
- the polymer unit is vinyl, stryl, acryl, or cyclic monomers selected from lactones, epoxides, lactides, lactams, silicon-containing cyclic monomers, and cyclic carbonates;
- provided that one of A or B has two methoxy substituents.
7 more elements
A composition comprising Formula Bz-4, Formula Bz-5, Formula Bz-6, or Formula Bz-7:
- wherein:
- dashed lines indicate optional bonds;
- X is O, S, NH, Ge, NC(O)—O—RC, N—O—C(O)RC, or NO—RC, wherein RC is alkyl, aryl, or heteroaryl;
- each of A and B is a phenyl ring;
- Z is OH or H;
- Y is OH, alkoxy, halo, SH, S-alkyl, carboxy, aryloxy, or a hetero-atom;
- substituents RA1 to RA5 and RB1 to RB5 are any combination of H, alkyl, alkene, alkynes, aryl, heterocyclic, alkenyl halides, unsaturated enones, unsaturated ketones, unsaturated amides, unsaturated alcohols, unsaturated amines, unsaturated thiols, phosphonates, carboxylates, sulfonates, nitriles, thioethers, thioketones, azides, sulfides, disulfides, ethers, epoxides, nitrates, nitrites, nitro compounds, nitroso compounds, alkyl ketoesters, acylgermanes, metallocenes, organosilanes, oximes, imides, cyanates, isocyanates, thiocyanates, isothiocyanates, sulfoxides, sulfones, sulfites, phosphites, thial, phosphines, and aldehydes;
- the co-initiating unit is an amine, a thiol, or any hydrogen atom donor;
- and
- the polymer unit is vinyl, stryl, acryl, or cyclic monomers selected from lactones, epoxides, lactides, lactams, silicon-containing cyclic monomers, and cyclic carbonates.
7 more elements
A method for making a polymer, the method comprising exposing a photoinitiator and a monomer to light to produce a polymer, wherein the photoinitiator is a biomass derived benzoin derivative having two methoxy substituents on one phenyl ring.
Dependencies are inferred from the claim text.