IP Library Granted Patent US 11,274,220
Granted Patent B2
US 11,274,220 · App. 15/764,924 · Granted Mar 15, 2022

Hydrophobic extenders in non-fluorinated surface effect coatings

Inventors: Gerald Oronde Brown (Swedesboro, NJ); John Christopher Sworen (Lincoln University, PA); Charles Karanja (Newark, DE)
Assignee: THE CHEMOURS COMPANY FC, LLC
C09D7/63C08F220/24C08J7/044C08J7/0427C08J7/054C09D5/00C09D5/1681C09D7/40C09D133/10D06M13/148D06M13/165D06M13/17D06M13/224D06M15/263D06M23/10C08F2/22C08F2/44C08J2367/00C08J2377/00C08K5/103C08K5/11C08K5/1535C09D7/47D06M2101/32D06M2101/34D06M2200/01D06M2200/11D06M2200/12
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Quick Facts
Patent No.
US 11,274,220
App. No.
15/764,924
Granted
Mar 15, 2022
Kind
B2
Abstract

The present invention relates to a coated article comprising a partial or complete durable non-fluorinated coating on the surface of an article, wherein the coating comprises 5 to 95% by weight of a hydrophobic compound, and 5 to 95% by weight of a surface effect agent, both based on the total solids weight of the coating, where the hydrophobic compound is selected from a hydrophobic cyclic or acyclic alcohol.

Claims (87)

1. A coated article comprising a complete durable non-fluorinated coating on a surface of an article,

wherein the coating is in the form of an aqueous solution, aqueous dispersion, organic solvent solution or dispersion, or cosolvent solution or dispersion,

wherein the coating comprises 10 to 90% by weight of a hydrophobic compound, and 10 to 90% by weight of at least one surface effect agent, both based on the total solids weight of the coating; wherein

the surface effect agent is in the form of at least one of hydrophobic non-fluorinated cationic acrylic polymers, hydrophobic non-fluorinated anionic acrylic polymers, hydrophobic non-fluorinated nonionic acrylic polymers, hydrophobic non-fluorinated urethanes, non-fluorinated organosilanes, silicones, or mixtures thereof;

each n is independently 0 to 20;

each m is independently 0 to 20;

m+n is greater than 0;

each R 1 is independently a linear or branched alkyl group having 5 to 29 carbons; and

each R 2 is independently a linear or branched alkyl group having 6 to 30 carbons;

wherein if the surface effect agent is a hydrophobic non-fluorinated urethane, the coating is in the form of an aqueous solution or an aqueous dispersion; and

wherein the hydrophobic compound has formula (Ia):

wherein each R is independently —H; —R 1 ; —C(O)R 1 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ; or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 ;

each n is independently 0 to 20;

each m is independently 0 to 20;

m+n is greater than 0;

r is 1 to 3;

a is 0 or 1;

p is independently 0 to 2;

provided that a is 0 when r is 3;

each R 1 is independently a linear or branched alkyl group having 5 to 29 carbons;

each R 2 is independently a linear or branched alkyl group having 6 to 30 carbons; and

at least one R is —H and at least two R groups are a —R 1 ; —C(O)R 1 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ; or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 .

2. The coated article of claim 1 , where the hydrophobic compound is selected from formula (Ia) to be formula (Ia′):

wherein R is further limited to independently —H; —R 1 ; or —C(O)R 1 .

3. The coated article of claim 1 , where the hydrophobic compound is selected from formula (Ia) to be formula (la′):

wherein R is further limited to independently —H; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ; or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 .

4. The coated article of claim 1 , wherein the surface effect is no iron, easy to iron, shrinkage control, wrinkle free, permanent press, moisture control, softness, strength, anti-slip, anti-static, anti-snag, anti-pill, stain repellency, stain release, soil repellency, soil release, water repellency, oil repellency, odor control, antimicrobial, sun protection, anti-blocking, cleanability, dust resistance, leveling, corrosion resistance, acid resistance, anti-fog, anti-ice, or tanning.

5. The coated article of claim 1 , where the coating comprises 20 to 80% by weight of a hydrophobic compound, and 20 to 80% by weight of a surface effect agent, both based on the total solids weight of the coating.

6. The coated article of claim 1 wherein the article is a fiber, textile, fabric, fabric blend, paper, nonwoven, leather, proppant particle, inorganic oxide particle, unglazed concrete, brick, tile, granite, limestone, marble, grout, mortar, statuary, monument, glass, thermoplastic sheet, thermoformed or molded article, foam sheet or article, metal, seed, painted fabric or canvas, or a combination thereof.

7. The coated article of claim 1 , wherein if the surface effect agent is a hydrophobic non-fluorinated urethane, the hydrophobic non-fluorinated urethane is a reaction product of an isocyanate compound and a cyclic or acyclic alcohol substituted with at least two —R 1 , —C(O)R 1 ,

(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 , —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 , or mixtures thereof, where:

each n is independently 0 to 20;

each m is independently 0 to 20;

m+n is greater than 0;

each R 1 is independently a linear or branched alkyl group having 5 to 29 carbons; and

each R 2 is independently a linear or branched alkyl group having 6 to 30 carbons.

8. A method of imparting a surface effect to an article comprising contacting a surface of the article with a durable non-fluorinated coating to form a completely coated article,

wherein the coating is in the form of an aqueous solution, aqueous dispersion, organic solvent solution or dispersion, or cosolvent solution or dispersion,

wherein the coating comprises 10 to 90% by weight of a hydrophobic compound, and 10 to 90% by weight of at least one surface effect agent, both based on the total solids weight of the coating; wherein

the surface effect agent is in the form of at least one of hydrophobic non-fluorinated cationic acrylic polymers, hydrophobic non-fluorinated anionic acrylic polymers, hydrophobic non-fluorinated nonionic acrylic polymers, hydrophobic non-fluorinated urethanes, non-fluorinated organosilanes, silicones, or mixtures thereof;

each n is independently 0 to 20;

each m is independently 0 to 20;

m+n is greater than 0;

each R 1 is independently a linear or branched alkyl group having 5 to 29 carbons; and

each R 2 is independently a linear or branched alkyl group having 6 to 30 carbons;

wherein if the surface effect agent is a hydrophobic non-fluorinated urethane, the coating is in the form of an aqueous solution or an aqueous dispersion; and

wherein the hydrophobic compound has formula (Ia):

wherein each R is independently —H; —R 1 ; —C(O)R 1 ;

—(CH 2 CH 2 O) n CH(CH 3 )CH 2 O) m R 2 ; or —(CH 2 CH 2 O) n (CH(CH)CH 2 O) m C(O)R 1 ;

each n is independently 0 to 20;

each m is independently 0 to 20;

m+n is greater than 0;

r is 1 to 3;

a is 0 or 1;

p is independently 0 to 2;

provided that a is 0 when r is 3;

each R 1 is independently a linear or branched alkyl group having 5 to 29 carbons;

each R 2 is independently a linear or branched alkyl group having 6 to 30 carbons; and

at least one R is —H and at least two R groups are a —R 1 ; —C(O)R 1 ;

—(CH 2 CH 2 O) n CH(CH 3 )CH 2 O) m R 2 ; or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 .

9. The method of claim 8 , further comprising the step of heating the completely coated article.

10. The method of claim 8 , further comprising the step of solidifying the coating by drying, cooling, or allowing to cool.

11. The method of claim 8 , where the step of contacting is by spraying, rolling, dip-squeeze, painting, sprinkling, dripping, powder coating, mixing the article in a liquid carrier of the hydrophobic compound, tumbling, or screen printing.

12. The method of claim 8 , where the stop of contacting occurs inside a laundry machine.

13. A coated article comprising a complete durable non-fluorinated coating on a surface of an article,

wherein the coating comprises 10 to 90% by weight of a hydrophobic compound, and 10 to 90% by weight of at least one surface effect agent, both based on the total solids weight of the coating; wherein

the surface effect agent is in the form of at least one of hydrophobic non-fluorinated cationic acrylic polymers, hydrophobic non-fluorinated anionic acrylic polymers, hydrophobic non-fluorinated nonionic acrylic polymers, hydrophobic non-fluorinated urethanes, non-fluorinated organosilanes, silicones, or mixtures thereof;

each n is independently 0 to 20;

each m is independently 0 to 20;

m+n is greater than 0;

each R 1 is independently a linear or branched alkyl group having 5 to 29 carbons; and

each R 2 is independently a linear or branched alkyl group having 6 to 30 carbons;

wherein if the surface effect agent is a hydrophobic non-fluorinated urethane, the coating is in the form of an aqueous solution or an aqueous dispersion;

wherein the hydrophobic compound has formula (Ia):

wherein each R is independently —H; —R 1 ; —C(O)R 1 ;

—(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ; or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 ;

each n is independently 0 to 20;

each m is independently 0 to 20;

m+n is greater than 0;

r is 1 to 3;

a is 0 or 1;

p is independently 0 to 2;

provided that a is 0 when r is 3;

each R 1 is independently a linear or branched alkyl group having 5 to 29 carbons;

each R 2 is independently a linear or branched alkyl group having 6 to 30 carbons; and

at least one R is —H and at least two R groups are a —R 1 ; —C(O)R 1 ;

—(CH 2 CH 2 O) n CH(CH 3 )CH 2 O) m R 2 ; or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 .

Assignments (2)
SECURITY INTEREST Recorded May 3, 2019
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 049080/0482 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 30, 2018
From: BROWN, GERALD ORONDE; SWOREN, JOHN CHRISTOPHER; KARANJA, CHARLES
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 045394/0022 →