Dyes with changeable solubilities, and methods for their use
View Patent ↗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.
1. 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;
R a is a halogen, or —NR b —W group;
R b is H or an alkyl group; and
W comprises a phenyl, naphthyl or anthracenyl group.
2. 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.
3. 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.
4. 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;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 may be the same or different and are independently H, Cl, Br, F, I, —NO 2 , —OH, alkyl, aryl, or —S(═O) 3 R 12 ;
R 8 , R 9 , R 10 , and R 11 may be the same or different and are independently H or alkyl; and
R 12 is H or an alkali metal.
5. The dye compound of claim 1 , wherein Z is an alkyl group, a cycloalkyl group, or an aryl group.
6. The dye compound of claim 1 , wherein L is a direct bond, an ester, ether, amide, carbonyl, phosphate, sulfoxide, nitrophenyl, nitrobenzyl, alkoxybenzoin, phenacyl, or benzylthioether group.
7. 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. The method of claim 7 , further comprising washing the substrate with water to remove the hydrophilic dye moiety after exposing the dye composition to the stimulus.
9. The method of claim 7 , wherein the substrate is selected from the group consisting of fabric, paper, plastics, glass, metals, wood, hair, fur, oils, waxes, leather and food.
10. The method of claim 7 , wherein the substrate is a fabric.
11. The dye compound of claim 2 , wherein Z is an alkyl group, a cycloalkyl group, or an aryl group.
12. The dye compound of claim 3 , wherein Z is an alkyl group, a cycloalkyl group, or an aryl group.
13. The dye compound of claim 4 , wherein Z is an alkyl group, a cycloalkyl group, or an aryl group.
14. The dye compound of claim 2 , wherein L is a direct bond, an ester, ether, amide, carbonyl, phosphate, sulfoxide, nitrophenyl, nitrobenzyl, alkoxybenzoin, phenacyl, or benzylthioether group.
15. The dye compound of claim 3 , wherein L is a direct bond, an ester, ether, amide, carbonyl, phosphate, sulfoxide, nitrophenyl, nitrobenzyl, alkoxybenzoin, phenacyl, or benzylthioether group.
16. The dye compound of claim 4 , wherein L is a direct bond, an ester, ether, amide, carbonyl, phosphate, sulfoxide, nitrophenyl, nitrobenzyl, alkoxybenzoin, phenacyl, or benzylthioether group.