Acid dyeing of polyurethane materials

Patent metadata

Field	Value
Publication number	US-9970155-B2
Application number	US-201313786056-A
Country	US
Kind code	B2
Filing date	Mar 5, 2013
Priority date	Mar 5, 2013
Publication date	May 15, 2018
Grant date	May 15, 2018

Abstract

A polyurethane is dyed with an aqueous solution of an acid dye compound, a quaternary ammonium compound selected from soluble tetrabutylammonium compounds and tetrahexylammonium compounds, and, optionally, an water-soluble organic solvent.

First claim

What is claimed is:

1. An aqueous dye solution for dyeing an article comprising a polyurethane material, the aqueous dye solution comprising:
from about 0.5 to about 5.0 g/L of an acid dye compound;
0.5 to 4 equivalents, per equivalent of the acid dye compound, of a soluble quaternary ammonium compound, the soluble quaternary ammonium compound selected from the group consisting of: tetrabutylammonium bromide, tetrabutylammonium chloride, tetrahexylammonium bromide, and tetrahexylammonium chloride; and
from about 5% to about 15% by volume of a water-soluble organic solvent comprising a member selected from the group consisting of n-propanol and isopropanol.

2. An aqueous dye solution according to claim 1 , wherein the soluble quaternary ammonium compound is selected from the group consisting of tetrahexylammonium bromide and tetrahexylammonium chloride.

3. An aqueous dye solution according to claim 1 , wherein the water-soluble organic solvent comprises n-propanol.

4. An aqueous dye solution according to claim 1 , consisting of water, from about 0.5 to about 5.0 g/L of the acid dye compound, 0.5 to 4 equivalents, per equivalent of the acid dye compound, of the soluble quaternary ammonium compound and from about 5% to about 15% by volume of the water-soluble organic solvent.

5. A method of dyeing an article comprising a thermoplastic polyurethane material, comprising:
immersing the thermoplastic polyurethane material in an aqueous dye solution at a temperature of about 30° C. to about 60° C. for a time sufficient for the aqueous dye solution to color the thermoplastic polyurethane material,
wherein the thermoplastic polyurethane material is a reaction product of one or more polyester diols, one or more compounds having at least two isocyanate groups, and optionally one or more chain extension compounds, wherein each of the one or more polyester diols has a weight average molecular weight of at least about 500, and wherein the one or more compounds having at least two isocyanate groups is selected from the group consisting of: isophorone diisocyanate (IPDI), methylene bis-4-cyclohexyl isocyanate (H 12 MDI), cyclohexyl diisocyanate (CHDI), m-tetramethyl xylene diisocyanate (m-TMXDI), p-tetramethyl xylene diisocyanate (p-TMXDI), ethylene diisocyanate, 1,2-diisocyanatopropane, 1,3-diisocyanatopropane, 1,6-diisocyanatohexane (hexamethylene diisocyanate or HDI), 1,4-butylene diisocyanate, lysine diisocyanate, 1,4-methylene bis-(cyclohexyl isocyanate), toluene diisocyanate, meta-xylylenediioscyanate, para-xylylenediisocyanate, 4-chloro-1,3-phenylene diisocyanate, 1,5-tetrahydro-naphthalene diisocyanate, 4,4′-dibenzyl diisocyanate, and 1,2,4-benzene triisocyanate, xylylene diisocyanate (XDI), diphenylmethane diisocyanate (MDI), and combinations thereof, and
wherein the aqueous dye solution comprises:
from about 0.001 to about 5.0 g/L of an acid dye compound;
0.5 to 4 equivalents, per equivalent of the acid dye compound, of a soluble quaternary ammonium compound, the soluble quaternary ammonium compound selected from tetrabutylammonium compounds and tetrahexylammonium compounds; and
optionally, from about 1% to about 50% by volume of a water-soluble organic solvent comprising a member selected from the group consisting of esters, ketones, glycol ether esters, and alcohols selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, propylene glycol monomethyl ether, dipropylene glycol, tripropylene glycol, glycerol, and glycol ethers; and

removing the thermoplastic polyurethane material from the aqueous dye solution.

6. A method according to claim 5 , wherein the thermoplastic polyurethane material comprises a member selected from the group consisting of thermoplastic polyurethane and thermoplastic polyurethane-containing fibers, yarns, threads, filaments, hanks, spools, sheets, woven and nonwoven fabrics, felts, fleeces, membranes, carpets, molded articles, articles of footwear, straps, synthetic leathers, and bladders and articles having thermoplastic polyurethane or a blend including thermoplastic polyurethane as at least a portion of a surface.

7. A method according to claim 5 , wherein the thermoplastic polyurethane material comprises a polyester-polyurethane or polyether-polyurethane.

8. A method according to claim 5 , wherein the aqueous dye solution further comprises the water-soluble organic solvent and the water-soluble organic solvent comprises a member selected from the group consisting of esters, glycol ether esters, and alcohols selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, propylene glycol monomethyl ether, dipropylene glycol, tripropylene glycol, glycerol, and glycol ethers.

9. A method according to claim 5 , wherein the aqueous dye solution consists of:
water;
from about 0.001 to about 5.0 g/L of the acid dye compound;
0.5 to 4 equivalents, per equivalent of the acid dye compound, of the soluble quaternary ammonium compound, the soluble quaternary ammonium compound selected from tetrabutylammonium compounds and tetrahexylammonium compounds; and
from about 1% to about 50% by volume of the water-soluble organic solvent comprising a member selected from the group consisting of esters, glycol ether esters, and alcohols selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, propylene glycol monomethyl ether, dipropylene glycol, tripropylene glycol, glycerol, and glycol ethers.

10. A method according to claim 5 , wherein the one or more polyester diols comprises a polyester of adipic acid and butanediol.

11. A method according to claim 10 , wherein the thermoplastic polyurethane article is a reaction product of the polyester of adipic acid and butanediol, diphenylmethane diisocyanate (MDI), and butanediol.

12. A method according to claim 6 , wherein the thermoplastic polyurethane material comprises the bladder, wherein the bladder comprises a multi-layer laminate membrane having a thermoplastic polyurethane outer layer that is at least 0.4 mils thick.

13. A method according to claim 6 , wherein the thermoplastic polyurethane material comprises the nonwoven fabric.

14. A method according to claim 5 , wherein the soluble quaternary ammonium compound is selected from the group consisting of: tetrahexylammonium bromide and tetrahexylammonium chloride.

15. A method according to claim 5 , wherein the immersing comprises immersing the thermoplastic polyurethane material in the aqueous dye solution for ten minutes.

16. An article dyed by the method of claim 5 .

17. A sheet, fabric, synthetic leather, or airbag according to claim 16 .

18. An article of footwear or strap comprising a sheet, fabric, synthetic leather, or airbag according to claim 17 .

Assignees

• Nike Inc

Inventors

• Schoborg Anna
• Matsuda-Dunn Reiko
• Watkins Richard L
• Chang Yihua

Classifications

• D06P3/241 Primary

  using acid dyes · CPC title

• D06P1/90

  using dyes dissolved in organic solvents or aqueous emulsions thereof {(D06P1/94 takes precedence)} · CPC title

• D06P1/66

  containing quaternary ammonium groups · CPC title

• C09B67/0083

  Solutions of dyes · CPC title