IP Library Granted Patent US 12,516,471
Granted Patent B1
US 12,516,471 · App. 17/174,443 · Granted Jan 6, 2026

Methods of imparting color to nylon substrates

Inventors: Rick Anderson (Toledo, OH); Nathan Anderson (Toledo, OH); Gregory Baden (Toledo, OH)
Assignee: Southwire Company, LLC
D06P3/241D06B5/02D10B2331/02
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,516,471
App. No.
17/174,443
Granted
Jan 6, 2026
Kind
B1
Abstract

Provided are methods of continuously imparting a desired characteristic, optionally color, to a linear polymeric substrate with reliability and reproducibility. According to some aspects, a method of continuously bonding an active agent to or into a polymeric substrate may include contacting an active agent solution with a polymeric substrate. Contacting the active agent solution with the polymeric substrate may occur at a treatment temperature and for a treatment time. The active agent solution may have been prepared from a method including diluting the treated active agent precursor solution to form the active agent solution.

Claims (29)

1 . A continuous method of contacting an active agent to a linear synthetic polymeric substrate to impart a color to the linear synthetic polymeric substrate, the method comprising:

contacting an active agent precursor solution with a cation exchange resin (CER), the contacting forming a treated active agent precursor solution;

diluting a first portion of the treated-active agent precursor solution to form an active agent solution;

contacting the active agent solution with the polymeric substrate at a treatment temperature and for a treatment time; and

adding a second portion the treated-active agent precursor solution to the active agent solution to maintain a concentration of the active agent in the active agent solution;

wherein:

the polymeric substrate comprises a polyamide polymeric material;

the active agent precursor solution comprises an active agent comprising an acid dye selected from the group consisting of an anthraquinone acid dye, an azo acid dye, and a triphenylmethane acid dye;

the CER comprises sulfonic acid functional groups;

a concentration of the active agent in the active agent precursor solution is in a range from 10 g/L to 50 g/L;

wherein a mass concentration of the active agent in the active agent precursor solution is in a range from 400% to 1000% relative to a mass concentration of the active agent in the active agent solution; and

a ΔE of the polymeric substrate is less than that of an otherwise identical continuous method comprising contacting the active agent solution with the cation exchange resin instead of contacting the active agent precursor solution with the cation exchange resin.

2 . The method of claim 1 , wherein the treated active agent solution comprises a salt.

3 . The method of claim 2 , wherein a concentration of the salt in the treated active agent precursor solution is from 0.1 g/L to 0.5 g/L.

4 . The method of claim 1 , wherein the treatment temperature is from 10° C. to 99° C.

5 . The method of claim 1 , wherein the treatment time is from 0.001 second to 30 minutes.

6 . The method of claim 1 , wherein the polymeric material comprises one or more of nylon 6, nylon 66, nylon 6/6-6, nylon 6/9, nylon 6/10, nylon 11, nylon 12, or any combination thereof.

7 . The method of claim 6 , wherein the acid dye comprises one or more of Acid Blue #60, Acid Blue #260, Acid Red #151, Acid Red #407, Acid Red #151, Mordant Red 7, Acid Red #1, Acid Black #2, Acid Yellow #23, Acid Yellow #43, Acid Yellow #36, Acid Yellow #232, Acid Orange #144, Acid Black #107, Acid Violet #90, and Acid Violet #17.

8 . The method of claim 1 , wherein the active agent precursor solution is an aqueous solution of an acid dye.

9 . The method of claim 1 , wherein the active agent precursor solution is contacted with the CER 2 or more times.

10 . The method of claim 1 , wherein the amount of CER, in equivalents is 0.1 to 10 times the moles of active agent exposed to the resin in the active agent precursor solution.

11 . The method of claim 1 wherein the treated active agent precursor solution is continuously or discontinuously supplied to the active agent solution during the treatment time.

12 . The method of claim 1 , wherein the mass concentration of the active agent in the active agent precursor solution is in a range from 600% to 1000% relative to a mass concentration of the active agent in the active agent solution.

13 . The method of claim 1 , wherein adding the second portion of the treated active agent precursor solution to the active agent solution to maintain a concentration of the active agent in the active agent solution comprises a plurality of additions of the second portion of the treated-active agent precursor solution to the active agent solution.

14 . The method of claim 1 , wherein the continuous process comprises at least 3 additions of the second portion of the treated active agent precursor solution to the active agent solution to maintain the concentration of the active agent in the active agent solution.

15 . The method of claim 1 , wherein the continuous process comprises at least 5 additions of the second portion of the treated active agent precursor solution to the active agent solution to maintain the concentration of the active agent in the active agent solution.

16 . The method of claim 1 , wherein a ΔE of 3 or less is maintained throughout the continuous method.

17 . The method of claim 1 , wherein the treatment temperature is in a range from 80° C. to 100° C.

18 . The method of claim 1 , wherein the cation exchange resin is a macroporous polystyrenic strong acid cation resin in hydrogen form with sulfonic acid functional groups.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 30, 2023
From: RADCO INFUSION TECHNOLOGIES, LLC
To: SOUTHWIRE COMPANY, LLC
Reel/Frame 062524/0546 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 9, 2022
From: ANDERSON GROUP, LTD.
To: RADCO INFUSION TECHNOLOGIES, LLC
Reel/Frame 062036/0114 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 3, 2021
From: ANDERSON, RICK; ANDERSON, NATHAN; BADEN, GREGORY
To: RADCO INFUSION TECHNOLOGIES, LLC
Reel/Frame 058012/0874 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 19, 2021
From: RADCO INFUSION TECHNOLOGIES, LLC
To: ANDERSON GROUP, LTD.
Reel/Frame 055960/0557 →
Continuity (3)
Continuation 16819839 · Mar 16, 2020
Continuation In Part 16743710 · Jan 15, 2020
Continuation In Part 16355173 · Mar 15, 2019
References Cited (66)
US 1887851A · Hinsky · 1932 [cited by applicant]
US 1890291A · Hinsky · 1932 [cited by applicant]
US 1944823A · Lamont · 1934 [cited by applicant]
US 2248965A · Corkery · 1941 [cited by applicant]
US 2499787A · Sharkey · 1950 [cited by examiner]
US 2543316A · Feild, Jr. et al. · 1951 [cited by applicant]
US 2766136A · Gray · 1956 [cited by applicant]
US 2986116A · Zerwes · 1961 [cited by applicant]
US 3225178A · Giot et al. · 1965 [cited by applicant]
US 3544388A · Russell · 1970 [cited by applicant]
US 3801359A · Polizzano et al. · 1974 [cited by applicant]
US 3814579A · Birke et al. · 1974 [cited by applicant]
US 3879973A · Godyn et al. · 1975 [cited by applicant]
US 4371371A · Smrekar · 1983 [cited by applicant]
US 4505222A · Holt et al. · 1985 [cited by applicant]
US 4592107A · von der Eltz · 1986 [cited by applicant]
US 4697291A · Shepherd et al. · 1987 [cited by applicant]
US 4702744A · Wolff · 1987 [cited by examiner]
US 4708887A · Baxter et al. · 1987 [cited by applicant]
US 4812140A · Russell · 1989 [cited by examiner]
US 4825491A · Miyamoto et al. · 1989 [cited by applicant]
US 5230709A · Holfeld et al. · 1993 [cited by applicant]
US 5897708A · Hsu · 1999 [cited by applicant]
US 6044509A · Schrell et al. · 2000 [cited by applicant]
US 6430980B1 · Weinhold et al. · 2002 [cited by applicant]
US 6443998B1 · Jones · 2002 [cited by examiner]
US 6652654B1 · Propp et al. · 2003 [cited by applicant]
US 6733543B2 · Pyles et al. · 2004 [cited by applicant]
US 7175675B2 · Pyles et al. · 2007 [cited by applicant]
US 7442877B2 · Kamata et al. · 2008 [cited by applicant]
US 7611547B2 · Bracken et al. · 2009 [cited by applicant]
US 7875309B2 · Kamata et al. · 2011 [cited by applicant]
US 7921680B2 · Kaczkowski et al. · 2011 [cited by applicant]
US 7968142B2 · Kamata et al. · 2011 [cited by applicant]
US 8286578B2 · Leenders et al. · 2012 [cited by applicant]
US 8586135B2 · Taniguchi et al. · 2013 [cited by applicant]
US 8624118B2 · Kauffman · 2014 [cited by applicant]
US 8968422B2 · Tutmark · 2015 [cited by applicant]
US 9064618B2 · Kuchta et al. · 2015 [cited by applicant]
US 20030124253A1 · Kamata et al. · 2003 [cited by applicant]
US 20060038356A1 · Lehtinen · 2006 [cited by applicant]
US 20060230553A1 · Thullen et al. · 2006 [cited by applicant]
US 20140250609A1 · Tutmark et al. · 2014 [cited by applicant]
US 20160086692A1 · Crawford et al. · 2016 [cited by applicant]
CN 101139689 · 2008 [cited by applicant]
CN 202594973U · 2012 [cited by applicant]
CN 202594975U · 2012 [cited by applicant]
CN 102856007A · 2013 [cited by applicant]
CN 103508682 · 2014 [cited by applicant]
CN 103508684 · 2014 [cited by applicant]
CN 103508685 · 2014 [cited by applicant]
CN 102856007B · 2014 [cited by applicant]
DE 3854608 · 1989 [cited by applicant]
DE 4308889 · 1994 [cited by applicant]
DE 10258234 · 2004 [cited by applicant]
EP 0068775A1 · 1983 [cited by applicant]
GB 1327699 · 1973 [cited by applicant]
GB 1401154 · 1975 [cited by examiner]
GB 1401154A · 1975 [cited by applicant]
GB 1427446 · 1976 [cited by applicant]
JP 11011802 · 1999 [cited by applicant]
JP 2003203530A · 2003 [cited by applicant]
JP 2009026475A · 2009 [cited by applicant]
WO 2009011182A1 · 2009 [cited by applicant]
WO 2016038335A1 · 2016 [cited by applicant]
SACMPH-H, Resin Tech https://www.resintech.com/product/sacmp-h/ Aug. 19, 2025. [cited by examiner]