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US 8,246,698 B2Granted
Dyes with changeable solubilities, and methods for their use
AssigneeEmpire Technology Development LLC
InventorSeth Adrian Miller
Life of this patent
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Abstract
Disclosed herein are solubility changeable dye compositions, methods of preparing such compositions and methods of using them. The composition includes a dye component linked via a linker moiety to a stimulus responsive hydrophobic moiety which modulates the solubility of the dye, wherein the hydrophobic moiety is configured to be de-linked from the dye component on exposure to a stimulus and render the dye component more hydrophilic.
Claims16
A dye compound comprising:
- a hydrophilic dye moiety;
- and
- a hydrophobic moiety bonded to the hydrophilic dye moiety through a linker moiety;
- wherein:
- the linker moiety is cleaved in response to a stimulus;
- the dye compound is represented by Formula (I)
- Z is the hydrophobic moiety;
- L is the linker moiety;
- Y is a phenyl or a naphthyl group;
- X is H, Cl, Br, F, or I;
- Ra is a halogen, or —NRb—W group;
- Rb is H or an alkyl group;
- and
- W comprises a phenyl, naphthyl or anthracenyl group.
11 more elements
A dye compound comprising:
- a hydrophilic dye moiety;
- and
- a hydrophobic moiety bonded to the hydrophilic dye moiety through a linker moiety;
- wherein:
- the linker moiety is cleaved in response to a stimulus;
- the dye compound is represented by Formula (II)
- Z is the hydrophobic moiety;
- L is the linker moiety;
- X is H, Cl, Br, F, or I;
- each Y independently comprises a phenyl or a naphthyl group;
- and
- W comprises a phenyl, naphthyl or anthracenyl group.
9 more elements
A dye compound comprising:
- a hydrophilic dye moiety;
- and
- a hydrophobic moiety bonded to the hydrophilic dye moiety through a linker moiety;
- wherein:
- the linker moiety is cleaved in response to a stimulus;
- the dye compound is represented by Formula (III)
- Z is the hydrophobic moiety;
- L is the linker moiety;
- X is H, Cl, Br, F, or I;
- each Y independently comprises a phenyl or a naphthyl group;
- and
- W comprises a phenyl, naphthyl, anthracenyl or pyrazolinyl group.
9 more elements
A dye compound comprising:
- a hydrophilic dye moiety;
- and
- a hydrophobic moiety bonded to the hydrophilic dye moiety through a linker moiety;
- wherein:
- the linker moiety is cleaved in response to a stimulus;
- the dye compound is represented by Formula (IV)
- Z is the hydrophobic moiety;
- L is the linker moiety;
- X is H, Cl, Br, F, or I;
- R1, R2, R3, R4, R5, R6, and R7 may be the same or different and are independently H, Cl, Br, F, I, —NO2, —OH, alkyl, aryl, or —S(═O)3R12;
- R8, R9, R10, and R11 may be the same or different and are independently H or alkyl;
- and
- R12 is H or an alkali metal.
10 more elements
A method for modulating the solubility of a dye compound comprising:
- exposing a dye composition to a stimulus;
- and
- contacting a substrate and the dye composition for a time period sufficient to covalently bond at least a portion of the plurality of the dye compounds to the substrate, prior to exposing the dye composition to the stimulus;
- wherein:
- the dye composition comprises:
- a plurality of the dye compounds, each dye compound comprising:
- a hydrophilic dye moiety;
- and
- a hydrophobic moiety bonded to the hydrophilic dye moiety through a linker moiety;
- and
- the linker moiety is cleaved in response to the stimulus.
8 more elements
Dependencies are inferred from the claim text.