IP Library Granted Patent US 12,247,093
Granted Patent B2
US 12,247,093 · App. 17/395,535 · Granted Mar 11, 2025

Water-repellent composition

Inventors: Kanako Takahashi (Osaka, JP); Rumi Kawabe (Osaka, JP); Miharu Ohta (Osaka, JP)
Assignee: DAIKIN INDUSTRIES, LTD.
C08F220/58C08F214/06C08F214/08C08G18/10C08G18/3853C08G77/20D06M15/248D06M15/263D06M15/285D06M2200/12
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Quick Facts
Patent No.
US 12,247,093
App. No.
17/395,535
Granted
Mar 11, 2025
Kind
B2
Abstract

A water-repellent composition containing (1) a polymer having 2-100 wt %, with respect to the polymer, of a repeating unit derived from an amide group-containing monomer (a) represented by the following formula [wherein R 1 is an organic moiety having an ethylenically unsaturated polymerizable group, R 2 is a C 7-30 hydrocarbon group, and R 3 is a C 1-5 hydrocarbon group], (2) a co-agent containing at least one co-agent compound selected from the group consisting of a blocked isocyanate compound, a melamine resin, a silicone polymer, a wax, an acetylene-based emulsifier, and a polyoxyalkylene group-containing emulsifier, and (3) a liquid media. Preferably, the water-repellent composition includes no fluoroalkyl group-containing monomer, and preferably no fluorine-containing monomer. Also disclosed is a method for producing the water-repellent composition, a method for treating a substrate with the water-repellent composition, and a method for producing a treated textile product which includes treating a textile product with the water-repellent composition.

Claims (53)

1. A water-repellent composition comprising:

(1) a polymer having 2 to 100% by weight, based on the amount of the polymer, of a repeating unit derived from (a) an amide group-containing monomer represented by the formula:

wherein R 1 is an organic residue having an ethylenically unsaturated polymerizable group,

R 2 is a hydrocarbon group having 7 to 30 carbon atoms, and

R 3 is a hydrocarbon group having 1 to 5 carbon atoms;

(2) a combination agent comprising at least one combination compound selected from the group consisting of a blocked isocyanate compound, a melamine resin, a silicone polymer, and a wax; and

(3) a liquid medium.

2. The water-repellent composition according to claim 1 , wherein, in the monomer (a), R 1 is-C(═O) CR 11 ═CH 2 , wherein R 11 is a hydrogen atom or a methyl group.

3. The water-repellent composition according to claim 1 , wherein

the polymer (1) further has a repeating unit derived from a polymerizable monomer other than the monomer (a), and

the polymerizable monomer other than the monomer (a) is a compound represented by the formula:

CH 2 =CA-T

wherein A is a hydrogen atom, a methyl group, a chlorine atom, a bromine atom, or an iodine atom, and

T is a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a chained or cyclic hydrocarbon group having 1 to 40 carbon atoms, or a chained or cyclic organic group having an ester bond and having 2 to 41 carbon atoms.

4. The water-repellent composition according to claim 3 , wherein

the polymerizable monomer other than the monomer (a) is at least one selected from the group consisting of:

(b) an acrylate ester monomer;

(c) a fluorine-free crosslinkable monomer; and

(d) a halogenated olefin monomer.

5. The water-repellent composition according to claim 4 , wherein the acrylate ester monomer (b) is at least one selected from the group consisting of:

(b1) an acrylate ester monomer having an aliphatic hydrocarbon group; and

(b2) an acrylate ester monomer having a cyclic hydrocarbon group,

the fluorine-free crosslinkable monomer (c) is a compound having at least two ethylenically unsaturated double bonds or a compound having at least one ethylenically unsaturated double bond and at least one reactive group, and

the halogenated olefin monomer (d) is at least one selected from the group consisting of vinyl chloride and vinylidene chloride.

6. The water-repellent composition according to claim 4 , wherein

in the polymer, the amount of the repeating unit (b) is 0 to 200 parts by weight, the amount of the repeating unit (c) is 0 to 50 parts by weight, and the amount of the repeating unit (d) is 0 to 100 parts by weight, based on 100 parts by weight of the repeating unit (a).

7. The water-repellent composition according to claim 1 , wherein

in the combination agent (2),

the blocked isocyanate compound is a compound having an isocyanate group moiety (a blocked isocyanate group) in which at least one isocyanate group is blocked with a blocking agent and having no polymerizable unsaturated group,

the melamine resin is a polycondensate of melamine and aldehyde,

the silicone polymer is a polymer represented by the formula:

(R 23 ) 3 Si—O—[—Si(R 21 ) 2 —O-] a -[—Si(R 21 )(R 22 )—O-] b -Si(R 23 ) 3

wherein each R 21 independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms,

each R 22 independently represents a saturated hydrocarbon group having 23 to 40 carbon atoms,

each R 23 independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a saturated hydrocarbon group having 23 to 40 carbon atoms,

a represents an integer of 0 or more, b represents an integer of 1 or more, and (a+b) is 5 to 200, and

in the wax, a compound constituting the wax has 20 to 60 carbon atoms.

8. The water-repellent composition according to claim 7 , wherein

the blocked isocyanate compound is a reaction product of an isocyanate represented by A(NCO) m , wherein A is a group remaining after isocyanate groups are removed from a polyisocyanate, and m is an integer of 2 to 8, and a blocking agent represented by RH, wherein R is a hydrocarbon group optionally substituted by a hetero atom, and H is a hydrogen atom,

the melamine resin is a partially or fully methylolated melamine resin obtained by a reaction between melamine and an aldehyde,

the silicone polymer is a compound represented by the formula:

wherein a represents an integer of 0 to 150,

b represents an integer of 1 to 150,

(a+b) is 5 to 200, and

n is an integer of 19 to 36, and

the wax is constituted by at least one compound selected from the group consisting of a normal alkane having 20 to 60 carbon atoms and a normal alkene having 20 to 60 carbon atoms.

9. The water-repellent composition according to claim 1 , wherein the liquid medium (3) is water, an organic solvent, or a mixture of water and an organic solvent.

10. An object obtained by treating the surface of the object with the water-repellent composition according to claim 1 .

11. A method for producing the water-repellent composition according to claim 1 , comprising mixing a polymer mixture which comprises the polymer (1) and the liquid medium (3) with the combination agent (2) comprising a combination compound.

12. A method for treating a substrate, comprising treating a substrate with the water-repellent composition according to claim 1 .

13. A method for producing a treated textile product, comprising treating a textile product with the water-repellent composition according to claim 1 .

14. A resin composition comprising a resin and the water-repellent composition according to claim 1 .

15. The water-repellent composition according to claim 1 , wherein the polymer (1) is a polymer having no fluoroalkyl group.

Assignments (2)
CHANGE OF ADDRESS Recorded Jan 11, 2023
From: DAIKIN INDUSTRIES LTD.
To: DAIKIN INDUSTRIES LTD.
Reel/Frame 062355/0697 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 3, 2021
From: TAKAHASHI, KANAKO; KAWABE, RUMI; OHTA, MIHARU
To: DAIKIN INDUSTRIES, LTD.
Reel/Frame 058016/0912 →
Priority Claims (1)
JP 2019-021692 · Feb 8, 2019 · national
Continuity (2)
Continuation PCTJP2020004580 · Feb 6, 2020
Related Publication 20210363280A1 · Nov 25, 2021
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