Modified Indigo Compounds and Methods of Dyeing a Substrate Using a Modified Indigo Compound
AssigneeThe H.D. Lee Company, Inc.
InventorsSudhakar Puvvada, Dennis Scheer, Paul Gerard Hoertz, Amsarani Ramamoorthy, Rajeev Rajbhandari, Caroline Elizabeth Hagerman, Alexander Peter Dirk Massey, Alexander Mark Hellawell, Asadollah Fallah, Ruhksana Quyoum
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Abstract
The present disclosure provides dye compounds for use in dyeing textiles.
Claims20
A dye compound for use in dyeing a substrate, the dye compound comprising an indigo derivative, or a salt thereof, having one or more modification over the chemical structure of indigo, wherein the indigo derivative has a water-solubility of greater than 0.2% w/v in the absence of a reducing agent and in the presence oxygen, and converts to indigo upon removing the modification, wherein the chemical structure of indigo is the following:
A compound which is of Formula (I) or (II):
- wherein:
- R1 and R2 are, independently, H, SO3RC, SO2RC, PO3(RC)2, C(O)NRARB, C(O)-(optionally substituted C1-6alkyl), C(O)-(optionally substituted aryl), C(O)-(optionally substituted C1-9glycolyl), C(O)-(optionally substituted heteroaryl), C(O)-(optionally substituted heterocyclyl), C(O)-(optionally substituted C1-6hydroxyalkyl), C(O)O-(optionally substituted C1-6alkyl), C(O)O-(optionally substituted aryl), C(O)O-(optionally substituted C1-9glycolyl), C(O)O-(optionally substituted C1-6hydroxyalkyl), C(O)O-(optionally substituted heteroaryl), C(O)O-(optionally substituted heterocyclyl);
- or
- R3 and R4 are, independently, H, halide, optionally substituted C1-6alkyl, optionally substituted C1-6hydroxyalkyl, optionally substituted C1-6alkoxy, optionally substituted aryl, or SO3H;
- R7 and R8 are, independently, H, SO3RC, SO2RC, PO3(RC)2, C(O)NRARB, C(O)-(optionally substituted C1-6alkyl), C(O)-(optionally substituted aryl), C(O)-(optionally substituted C1-9glycolyl), C(O)-(optionally substituted C1-6hydroxyalkyl), C(O)-(optionally substituted heteroaryl), C(O)-(optionally substituted heterocyclyl), C(O)O-(optionally substituted C1-6alkyl), C(O)O-(optionally substituted aryl), C(O)O-(optionally substituted C1-9glycolyl), C(O)O-(optionally substituted C1-6hydroxyalkyl), C(O)O-(optionally substituted heteroaryl), or C(O)O-(optionally substituted heterocyclyl);
- RA and RB are, independently, H or optionally substituted C1-6alkyl, or optionally substituted aryl;
- RC is H, optionally substituted C1-6alkyl, optionally substituted C3-8cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted heterocyclyl;
- m and n are, independently, 0 to 4;
- or a salt thereof.
A method of dyeing a substrate, comprising:
- (i) contacting the substrate with an aqueous bath comprising a compound comprising an indigo derivative, or a salt thereof, having one or more modification over the chemical structure of indigo, wherein the indigo derivative has a water-solubility of greater than 0.2% w/v in the absence of a reducing agent and in the presence oxygen, and converts to indigo upon removing the modification;
- and
- (ii) hydrolyzing the compound of step (i).
Dependencies are inferred from the claim text.