Process for dyeing high-performance textiles
AssigneeThe Government of the United States, as represented by the Secretary of the Army
InventorsChristopher Doona, Richard Liu, Timothy Swager
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Abstract
The present disclosure relates to methods and compositions used therein to dye via a bifunctional diazirene compound high-performance textiles including para-aramid (polymers of co-polymers), ultra-high molecular weight polyethylene (UHMWPE), or nylon as filament yarns and/or spun yarns of fibers or fiber-blends thereof and in a manner more quickly and more environmentally friendly.
Claims15
A method of dyeing textiles including surface functionalization with a carbene-based molecule, comprising:
- reacting the textile with a bifunctional diazirene reagent 4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzyl bromide “anchor” molecule of the formula
- having a first terminus including a trifluoromethyl diazirine group as a carbene precursor and a second terminus including a benzyl bromide group, in the presence of ultraviolet radiation to form a textile surface bound to the first terminus of the bifunctional diazirene “anchor” molecule;
- and
- reacting the textile bound to the first terminus of the bifunctional diazirene “anchor” molecule with a dye molecule that covalently binds the second terminus of the bifunctional diazirene “anchor” molecule.
A method of dyeing textiles including surface functionalization of a textile fabric comprising Kevlar yarns with a carbene-based molecule, comprising:
- reacting the textile fabric comprising poly (p-phenylene terephthalamide yarns of the chemical formula
- with the bifunctional diazirene 4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzyl bromide “anchor” molecule of the formula
- having a first terminus including a trifluoromethyl diazirine group as a carbene precursor group and a second terminus including a benzyl bromide group, in the presence of ultraviolet radiation to form a textile fabric comprising poly (p-phenylene terephthalamide yarns bound to the first terminus of the bifunctional diazirene 4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzyl bromide “anchor” molecule to form a compound of the formula
- reacting the textile fabric comprising poly (p-phenylene terephthalamide yarns bound to the first terminus of the bifunctional diazirene 4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzyl bromide with an “anchor” molecule with a dye molecule of the formula
- in the presence of base to form dye bound to the second terminus of the bifunctional diazirene 4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzyl bromide “anchor” molecule of the textile fabric comprising poly (p-phenylene terephthalamide yarns to form a compound of the formula
A method of dyeing textiles including a para-aramid via surface functionalization of para-aramid with a carbene-based molecule, comprising:
- performing an Appel bromination reaction of 4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzyl alcohol 102 using carbon tetrabromide, dry dichloromethane and triphenylphosphine to form a bifunctional diazirene 4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzyl bromide “anchor” molecule of the formula
- reacting the para-aramid of the textile of the formula
- with the bifunctional diazirene 4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzyl bromide “anchor” molecule of the formula
- having a first terminus including a trifluoromethyl diazirine group as a carbene precursor group and a second terminus including a benzyl bromide group, in the presence of ultraviolet radiation to form a para-aramid fabric bound to the first terminus of the bifunctional diazirene 4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzyl bromide an “anchor” molecule of the formula
- reacting the para-aramid surface bound to the first terminus of the bifunctional diazirene 4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzyl bromide an “anchor” molecule with a dye molecule of the formula
- in the presence of base to form dye bound to the second terminus of the bifunctional diazirene 4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzyl bromide an “anchor” molecule on the para-aramid of the formula
Dependencies are inferred from the claim text.