IP Library › Granted Patent US 12,600,924
Granted Patent B2
US 12,600,924 · App. 17/645,560 · Granted Apr 14, 2026

Non-cationic softeners and methods of use

Inventors: Ashish Dhawan (Saint Paul, MN); Yiqing Chen (Saint Paul, MN); Carter M. Silvernail (Saint Paul, MN); Lee Monsrud (Saint Paul, MN); Gary Samuel Furman, Jr. (St. Chares, IL); Marisa Alves Da Rocha (Rijnsburg, NL)
Assignee: ECOLAB USA INC.
C11D3/30C11D3/0015C11D3/2096C11D3/3723D06M13/11D06M13/332D21H17/06D21H17/07D21H17/56C11D2111/12D06M2200/50
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Quick Facts
Patent No.
US 12,600,924
App. No.
17/645,560
Granted
Apr 14, 2026
Kind
B2
Abstract

A composition comprising a non-cationic amine epoxide adduct is disclosed, along with methods of making the same. Use of a composition comprising a non-cationic amine epoxide adduct on textiles and paper, particularly woven textiles, tissues, and nonwoven textiles to soften the textiles and paper, along with methods of using a non-cationic amine epoxide adduct to treat a target, are also disclosed.

Claims (33)

1 . A softened product comprising:

an amine epoxide adduct compound according to the formula:

wherein R is an alkyl group or a —(CH 2 ) k O-alkyl, and wherein k is an integer between 1-10 and n is an integer of between 1-1000;

a processing aid comprising a non-deliquescent material; and

a textile; and

wherein the softened product is free of quaternary ammonium compounds, and

wherein the amine epoxide adduct compound adheres to the textile.

2 . The softened product of claim 1 , wherein the amine epoxide adduct is a compound selected from the following formulas:

or a combination thereof.

3 . The softened product of claim 1 , wherein the textile is selected from silk fibers, linen fibers, cotton fibers, hemp fibers, angora fibers, bamboo fibers, polyester fibers, polyamide fibers, nylon, acrylic fibers, acetate fibers, wool, rayon, cashmere, satin, spandex, cotton, polyester, or a combination thereof.

4 . The softened product of claim 3 , wherein the textile is a fabric used in a hotel, hospital, healthcare facility, restaurant, health club, salon, retail store, or a combination thereof.

5 . The softened product of claim 4 , wherein the textile is a bed sheet, pillowcase, towel, table linen, tablecloth, bar mop, or uniform.

6 . The softened product of claim 1 , wherein the softened product comprises from about 10 wt. % to about 80 wt. % of the amine epoxide adduct compound.

7 . The softened product of claim 1 , wherein the softened product further comprises an additional functional ingredient selected from an alkalinity source, defoaming agent, anti-redeposition agent, solubility modifier, dispersant, stabilizing agent, sequestrant, chelating agent, surfactant, anti-wrinkling agent, optical brightener, dye, rheology modifier, thickener, hydrotrope, coupler, buffer, solvent, enzyme, soil-release agent, dye scavenger, crisping agent, antimicrobial agent, fungicide, antioxidant, or a combination thereof.

8 . The softened product of claim 1 , wherein the amine epoxide adduct compound comprises a molar ratio of the epoxide to the amine between about 1:20 to about 20:1.

9 . The softened product of claim 1 , wherein the amine epoxide adduct compound comprises one or more epoxides derived from an alkylene.

10 . The softened product of claim 1 , wherein the softened product is a solid comprising about 10 wt. % to about 80 wt. % amine epoxide adduct compound and about 0 wt. % to about 10 wt. % processing aid.

11 . The softened product of claim 1 , wherein the softened product is a liquid comprising about 10 wt. % to about 80 wt. % amine-epoxide adduct compound and about 0 wt. % to about 25 wt. % processing aid.

12 . The softened product of claim 1 , wherein the amine epoxide adduct is a multiple charged cationic compound having 1, 2, 3, or more positive charges.

13 . The softened product of claim 1 , wherein the amine epoxide adduct is a multiple charged anionic compound having 1, 2, 3, or more negative charges.

14 . The softened product of claim 1 , wherein the amine epoxide adduct compound comprises an epoxide consisting of a monoepoxide or a polyepoxide.

15 . The softened product of claim 1 , the amine epoxide adduct has a hydrophobicity and/or hydrophilicity and the alkyl groups and alkyl have a length of carbon chains, and wherein the length of the carbon chains and/or the amount of epoxides adjusts the hydrophobicity and/or hydrophilicity of the amine epoxide adduct.

16 . The softened product of claim 1 , wherein the amine used to generate the amine epoxide adduct compound is selected from pentaethylenehexamine, tetraethylenepentamine, diethylenetriamine, ethyleneamine E-100, triethylenetetramine, tris(2-aminoethyl)amine, or a combination thereof.

17 . The softened product of claim 1 , wherein the epoxide used to generate the amine epoxide adduct compound is selected from 1,2-epoxydodecane, 1,2-epoxytetradecane, 1,2-epoxyhexadecane, C 12 -C 14 alkyl glycidyl ether, C 8 -C 10 alkyl glycidyl ether, 2-ethylhexyl glycidyl ether, Styrene Oxide, or a combination thereof.

18 . The softened product of claim 1 , wherein the amine epoxide adduct compound is generated at a reaction temperature of between about 90° C. and about 140° C.

19 . A method of softening a product comprising:

contacting a first reagent comprising an amine and a second reagent comprising an epoxide to generate an amine epoxide adduct compound according to the formula:

wherein R is an alkyl group or a —(CH 2 ) k O-alkyl, and wherein k is an integer between 1-10 and wherein n is an integer of between 1-1000;

forming a mixture comprising the amine epoxide adduct compound and a processing aid comprising a non-deliquescent material; and

wherein the mixture is free of quaternary ammonium compounds; and

contacting the mixture with a product comprising a textile, wherein the amine epoxide adduct compound adheres to the textile.

20 . The method of claim 19 , wherein the amine is selected from pentaethylenehexamine, triethylenetetramine, tetraethylenepentamine, diethylenetriamine, hexaethyleneheptamine, or a combination thereof, or wherein the epoxide is selected from 1,2-epoxydodecane, 1,2-epoxytetradecane, 1,2-epoxyhexadecane, 1,2-epoxyoctadecane, a C 8 -C 10 alkyl glycidyl ether, a C 12 -C 14 alkyl glycidyl ether, or a combination thereof.

21 . The method of claim 19 , wherein the textile is a fabric used in a hotel, hospital, healthcare facility, restaurant, health club, salon, retail store, or a combination thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 22, 2021
From: DHAWAN, ASHISH; CHEN, YIQING; SILVERNAIL, CARTER M.; MONSRUD, LEE; FURMAN, GARY SAMUEL, JR.; ALVES DA ROCHA, MARISA
To: ECOLAB USA INC.
Reel/Frame 058461/0917 →
Continuity (2)
Provisional Application 63199408 · Dec 23, 2020
Related Publication 20220204889A1 · Jun 30, 2022
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