Fluorinated ester compound additives for architectural coatings

Patent metadata

Field	Value
Publication number	US-11518894-B2
Application number	US-201816623820-A
Country	US
Kind code	B2
Filing date	Jun 11, 2018
Priority date	Jun 26, 2017
Publication date	Dec 6, 2022
Grant date	Dec 6, 2022

Abstract

The present invention is a composition of (a) a coating base selected from a water-dispersed coating, an epoxy polymer coating, an alkyd coating, a Type I urethane coating, or an unsaturated polyester coating; and (b) a fluorinated ester compound having a plurality of fluoroalkyl thioether groups, wherein the number average molecular weight of the fluorinated ester compound is ≤30,000 Da; and where the fluorinated group R f is independently a straight or branched perfluoroalkyl group of 2 to 20 carbon atoms, which is optionally interrupted by one or more CH 2 , CFH, ether oxygens —O—, or combinations thereof. The fluorinated ester compounds provide cleanability to the resulting coating made from the present composition.

First claim

What is claimed is:

1. A composition comprising (a) a coating base selected from a water-dispersed coating, an epoxy polymer coating, an alkyd coating, a Type I urethane coating, or an unsaturated polyester coating; and (b) a fluorinated ester compound having a plurality of fluoroalkyl thioether groups, said fluorinated ester compound selected from Formula (I), Formula (II), Formula (III), or Formula (IV):

wherein
the number average molecular weight of the fluorinated ester compound is ≤30,000 Da;
R 1 is a linear or branched C 1 to C 4 alkyl group;
t is an integer of 2 to 4;
n is an integer 3;
x is independently an integer of 1 to 4;
y is independently an integer of 1 to 10;
Y is a linear or branched organic linking group that is divalent, trivalent, or tetravalent, selected from the group consisting of linear or branched C 1 to C 20 alkylene groups, carbonyl groups, thioether groups, aryl groups, cycloalkyl groups, ether groups, hydroxyl groups, —NHC(O)—, uretdione, allophanate, isocyanurate, and mixtures thereof; and
R f is independently a straight or branched perfluoroalkyl group of 2 to 20 carbon atoms, optionally interrupted by one or more CH 2 , CFH, ether oxygens —O—, or combinations thereof.

2. The composition of claim 1 , wherein the composition comprises (a) the coating base in an amount of from about 95 to 99.98% and (b) the fluorinated ester compound in an amount of from about 0.02 to 5% by weight, based on the total weight of (a) and (b).

3. The composition of claim 1 , where the fluorinated ester compound is selected from Formula (I) and t is 2 or 3.

4. The composition of claim 1 , where n is 3 to 15.

5. The composition of claim 1 , where Y is selected from the group consisting of —(CH 2 ) z C(R 2 )(OH)(CH 2 ) z —, an uninterrupted C 1 to C 20 linear or branched alkylene, —C(O)—C(O)—, —C(O)—(CH 2 ) z —S—(CH 2 ) r —S—(CH 2 ) z —C(O)—, —C(O)—(CH 2 ) z —O—(CH 2 ) r —O—(CH 2 ) z —C(O)—, —C(O)—(CH 2 ) z —S—C(R 2 )(R 3 )—S—(CH 2 ) z —C(O)—, —C(O)—(CH 2 ) z —O—C(R 2 )(R 3 )—O—(CH 2 ) z —C(O)—, —C(O)NH-A-NHC(O)—;
wherein z is an integer of 1 to 4; r is an integer of 1 to 20, R 2 is H, a linear or branched C 1 to C 6 alkyl group, or an aryl group; R 3 is H, a linear or branched C 1 to C 6 alkyl group, or an aryl group, and A is the residue from a polyisocyanate.

6. The composition of claim 5 , where z is 1 and R 2 is H.

7. The composition of claim 5 , where z is 2, R 2 is —CH 3 , and R 3 is —CH 2 CH(CH 3 ) 2 .

8. The composition of claim 1 , where the fluorinated ester compound (b) is water insoluble.

9. The composition of claim 1 , where the coating base is a water-dispersed coating in the form of an aqueous acrylic latex paint.

10. The composition of claim 1 , where the coating base comprises an additive selected from TiO 2 , clays, asbestos, calcium carbonate, zinc oxide, chromium oxide, barium sulfate, iron oxide, tin oxide, calcium sulfate, talc, mica, silicas, dolomite, zinc sulfide, antimony oxide, zirconium dioxide, silicon dioxide, cadmium sulfide, cadmium selenide, lead chromate, zinc chromate, nickel titanate, diatomaceous earth, glass fibers, glass powders, glass spheres, blue pigments, red pigments, yellow pigments, orange pigments, process aggregated crystals, brown pigments, or green pigments.

11. An article comprising a substrate and a dried coating thereon, where the dried coating results from drying a composition comprising (a) a coating base selected from a water-dispersed coating, an epoxy polymer coating, an alkyd coating, a Type I urethane coating, or an unsaturated polyester coating; and (b) a fluorinated ester compound having a plurality of fluoroalkyl thioether groups, said fluorinated ester compound selected from Formula (I), Formula (II), Formula (III), or Formula (IV):

wherein
the number average molecular weight of the fluorinated ester compound is 30,000 Da;
R 1 is a linear or branched C 1 to C 4 alkyl group;
t is an integer of 2 to 4;
n is an integer ≥3;
x is independently an integer of 1 to 4;
y is independently an integer of 1 to 10;
Y is a linear or branched organic linking group that is divalent, trivalent, or tetravalent, selected from the group consisting of linear or branched C 1 to C 20 alkylene groups, carbonyl groups, thioether groups, aryl groups, cycloalkyl groups, ether groups, hydroxyl groups, —NHC(O)—, uretdione, allophanate, isocyanurate, and mixtures thereof; and

R f is independently a straight or branched perfluoroalkyl group of 2 to 20 carbon atoms, optionally interrupted by one or more CH 2 , CFH, ether oxygens —O—, or combinations thereof.

12. The article of claim 11 , where Y is selected from the group consisting of —(CH 2 ) z C(R 2 )(OH)(CH 2 ) z —, an uninterrupted C 1 to C 20 linear or branched alkylene, —C(O)—C(O)—, —C(O)—(CH 2 ) z —S—(CH 2 ) r —S—(CH 2 ) z —C(O)—, —C(O)—(CH 2 ) z —O—(CH 2 ) r —O—(CH 2 ) z —C(O)—, —C(O)—(CH 2 ) z —S—C(R 2 )(R 3 )—S—(CH 2 ) z —C(O)—, —C(O)—(CH 2 ) z —O—C(R 2 )(R 3 )—O—(CH 2 ) z —C(O)—, —C(O)NH-A-NHC(O)—;
wherein z is an integer of 1 to 4; r is an integer of 1 to 20, R 2 is H, a linear or branched C 1 to C 6 alkyl group, or an aryl group; R 3 is H, a linear or branched C 1 to C 6 alkyl group, or an aryl group, and A is the residue from a polyisocyanate.

13. The article of claim 11 , wherein the composition comprises (a) the coating base in an amount of from about 95 to 99.98% and (b) the fluorinated ester compound in an amount of from about 0.02 to 5% by weight, based on the total weight of (a) and (b).

14. The article of claim 11 , where the coating base is a water-dispersed coating in the form of an aqueous acrylic latex paint.

15. The article of claim 11 , where the substrate is selected from the group consisting of wood, metal, wallboard, masonry, concrete, fiberboard, and paper.

16. The article of claim 11 , where the fluorinated ester compound is selected from Formula (I) and t is 2 or 3.

17. The article of claim 11 , where n is 3 to 15.

18. The article of claim 12 , where z is 1 and R 2 is H.

19. The article of claim 12 , where z is 2, R 2 is —CH 3 , and R 3 is —CH 2 CH(CH 3 ) 2 .

20. The article of claim 11 , where the coating base comprises an additive selected from TiO 2 , clays, asbestos, calcium carbonate, zinc oxide, chromium oxide, barium sulfate, iron oxide, tin oxide, calcium sulfate, talc, mica, silicas, dolomite, zinc sulfide, antimony oxide, zirconium dioxide, silicon dioxide, cadmium sulfide, cadmium selenide, lead chromate, zinc chromate, nickel titanate, diatomaceous earth, glass fibers, glass powders, glass spheres, blue pigments, red pigments, yellow pigments, orange pigments, process aggregated crystals, brown pigments, or green pigments.

Assignees

• Chemours Co Fc Llc

Inventors

• Lasio Jelena
• Ober Michael Henry
• Woerner Francis J
• Yim Hing

Classifications

• C09D7/65 Primary

  macromolecular (C09D7/41-C09D7/48 take precedence) · CPC title

• C08K5/10

  Esters; Ether-esters · CPC title

• C09D5/00

  Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes · CPC title

• C08K5/02

  Halogenated hydrocarbons {(C08K5/0091 takes precedence)} · CPC title

• C08K5/372

  Sulfides {, e.g. R-(S)x-R'} · CPC title