Acrylate oligomers, acrylate oligomer emulsions, and fluorine-free stain-release compositions containing the same

Patent metadata

Field	Value
Publication number	US-12590409-B2
Application number	US-202218272685-A
Country	US
Kind code	B2
Filing date	Feb 3, 2022
Priority date	Feb 3, 2021
Publication date	Mar 31, 2026
Grant date	Mar 31, 2026

Abstract

The present invention is an acrylate oligomer represented by the formula (I) where R 1 is hydrogen or methyl; R 2 is an alkyl group having from 2 to 18 carbons, inclusive; R 3 is hydrogen or hydroxyl; Y is hydrogen or an initiator residue; Z is a single bond or methylene; and n is an integer from 9 to 40, inclusive. The present invention also includes acrylate oligomer emulsions including the disclosed oligomer and fluorine-free treating compositions including the acrylate oligomer emulsion. Methods of making and using such compositions are also disclosed.

First claim

What is claimed is:

1 . An acrylate oligomer emulsion comprising:
an oligomer represented by the formula:

wherein
R 1 is hydrogen or methyl,
R 2 is an alkyl group having from 2 to 18 carbons, inclusive,
R 3 is hydrogen or hydroxyl,
Y is hydrogen or an initiator residue,
Z is a single bond or methylene, and
n is an integer from 9 to 40, inclusive;

water; and
a surfactant.

2 . The oligomer of claim 1 , wherein R 2 is an alkyl group having 2 to 4 carbons.

3 . The oligomer of claim 1 , wherein R 2 is t-butyl group.

4 . The oligomer of claim 1 , wherein n is 16 to 20.

5 . The oligomer of claim 1 , wherein the oligomer is made by the radical-initiated reaction of a reaction mixture comprising 2-mercaptoethanol and a (meth)acrylate.

6 . The oligomer of claim 5 , wherein the (meth)acrylate is selected from the group consisting of octadecyl acrylate, ethyl methacrylate, t-butyl acrylate, t-butyl methacrylate, and combinations thereof.

7 . The acrylate oligomer emulsion of claim 1 wherein the acrylate oligomer emulsion comprises 0.3 wt. % to 1.3 wt. % surfactant on a solids basis.

8 . The acrylate oligomer emulsion of claim 1 , further comprising a glycol and/or a preservative.

9 . A fluorine-free treating composition comprising:
0.1 wt. % to 4 wt. % solids on fabric of the acrylate oligomer emulsion of claim 1 ; water; and optionally an additive selected from the group consisting of a fabric softener, an antiwrinkle finish, a protective material, and combinations thereof.

10 . A method of treating a fibrous substrate, the method comprising:
preparing a fluorine-free treating composition of claim 9 ; applying the fluorine-free treating composition to a fibrous substrate in an amount sufficient to make the fibrous substrate exhibit stain release that is better than the stain release of a similar fibrous substrate without the composition applied.

11 . A fluorine-free treating composition comprising:
0.1 wt. % to 4 wt. % solids on fabric of a urethane oligomer emulsion comprising:
a urethane oligomer represented by the formula:

wherein
U Poly comprises a urethane polymer backbone,
R 1 is hydrogen or methyl,
R 2 is an alkyl group having from 2 to 18 carbons, inclusive,
R 3 is hydrogen or hydroxyl,
Y is hydrogen or an initiator residue,
Z is a single bond or methylene, and
n is an integer from 9 to 40, inclusive,

water; and
a surfactant;

and
optionally an additive selected from the group consisting of a fabric softener, an antiwrinkle finish, a protective material, and combinations thereof.

12 . The fluorine-free treating composition of claim 11 , further comprising a blocked isocyanate extender.

13 . A method of treating a fibrous substrate, the method comprising:
preparing a fluorine-free treating composition of claim 11 ; applying the fluorine-free treating composition to a fibrous substrate in an amount sufficient to make the fibrous substrate exhibit stain release that is better than the stain release of a similar fibrous substrate without the composition applied.

14 . A fluorine-free treating composition comprising:
0.1 wt. % to 4 wt. % solids on fabric of an acrylate oligomer emulsion comprising:
an oligomer represented by the formula:

wherein
R 1 is hydrogen or methyl,
R 2 is an alkyl group having from 2 to 18 carbons, inclusive,
R 4 is a hydrocarbon group,
Y is hydrogen or an initiator residue, and
n is an integer from 9 to 40, inclusive;

water; and
a surfactant;

and
optionally an additive selected from the group consisting of a fabric softener, an antiwrinkle finish, a protective material, and combinations thereof.

15 . A method of treating a fibrous substrate, the method comprising:
preparing a fluorine-free treating composition of claim 14 ; applying the fluorine-free treating composition to a fibrous substrate in an amount sufficient to make the fibrous substrate exhibit stain release that is better than the stain release of a similar fibrous substrate without the composition applied.

Assignees

• 3M Innovative Properties Company

Inventors

• Anderson Jeffrey T
• Hayes Michael T
• Nixon Angela J

Classifications

• D06M2200/12

  Hydrophobic properties · CPC title

• D06M2200/01

  Stain or soil resistance · CPC title

• D06M2101/34

  Polyamides · CPC title

• D06M2101/32

  Polyesters · CPC title

• D06M2101/06

  cellulosic · CPC title