IP Library Granted Patent US 11,459,485
Granted Patent B2
US 11,459,485 · App. 16/344,199 · Granted Oct 4, 2022

Non-fluorinated coating and finish agents

Inventors: Gerald Oronde Brown (Swedesboro, NJ); Tess Crosetto (Philadelphia, PA); Ewa Kohler (West Chester, PA); John Christopher Sworen (Lincoln University, PA)
Assignee: THE CHEMOURS COMPANY FC, LLC
C09D183/12C08G77/14C08K3/18C08L33/00C09D5/00C09D5/14C09D5/1625C09D5/1637C09D5/1675C09D7/63C09D7/65C09D133/02D06M15/233D06M15/263D06M15/267D06M15/647D06M15/6436D06M2200/01D06M2200/11D06M2200/12D06M2200/20D06M2200/30D06M2200/45D06M2200/50
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Quick Facts
Patent No.
US 11,459,485
App. No.
16/344,199
Granted
Oct 4, 2022
Kind
B2
Abstract

The present invention relates to a coating composition with 10 to 100% by weight of a non-fluorinated compound mixture, which comprises at least one compound b and at least one compound a, c, or d: a) alkali metal salt of poly(meth)acrylic acid, alkali metal salt of poly(meth)acrylic acid copolymer, ammonium compound or amine salt of poly(meth)acrylic acid, ammonium compound or amine salt of poly(meth)acrylic acid copolymer, or mixtures thereof; b) silicone polyether, alkali metal salt of silicone polyether carboxylate, ammonium compound or amine salt of silicone polyether carboxylate, or mixtures thereof; c) salt of hydrolyzed α-olefin/maleic anhydride copolymer, salt of esterified α-olefin/maleic anhydride copolymer, α-olefin/maleic anhydride copolymer amic acid resin or salt thereof, or mixtures thereof; or d) polycarboxylate calcium sequestrants or mixtures thereof. Such coatings exhibit improved soil and stain cleaning performance.

Claims (68)

1. A coating composition comprising 10 to 100% by weight of a non-fluorinated compound mixture, based on the total solids weight of the coating,

where the non-fluorinated compound mixture comprises at least one compound from b, and at least one compound from a or c:

a) an alkali metal salt of poly(meth)acrylic acid, ammonium compound salt of poly(meth)acrylic acid, amine salt of poly(meth)acrylic acid, or mixtures thereof;

b) silicone polyether, alkali metal salt of silicone polyether carboxylate, ammonium compound salt of silicone polyether carboxylate, amine salt of silicone polyether carboxylate, or mixtures thereof; or

c) alkali metal salt of hydrolyzed α-olefin/maleic anhydride copolymer, ammonium compound salt of hydrolyzed α-olefin/maleic anhydride copolymer, amine salt of hydrolyzed α-olefin/maleic anhydride copolymer, alkali metal salt of esterified α-olefin/maleic anhydride copolymer, ammonium compound or amine salt of esterified α-olefin/maleic anhydride copolymer, α-olefin/maleic anhydride copolymer amic acid resin, salt of α-olefin/maleic anhydride copolymer amic acid resin, or mixtures thereof;

where the non-fluorinated compound mixture has a pH of about 7 to about 10.5; and

where the at least one compound from b is from formula (I) or (II):

wherein

R 1 , R 2 , and R 3 are independently C 1 -C 8 alkyl groups;

X is a linear or branched C 1 -C 4 alkylene group;

R 4 is independently H or —C(O)—Y—C(O)O − M +;

Y is a linear or branched, saturated or unsaturated C 1 -C 5 alkylene group;

M is independently H, alkali metal, NH 4 + , dialkyl ammonium cation, or amine cation;

a and b are independently integers of 1 to 40 where a+b is an integer of at least 2; and

c and d are independently integers of 0 to 20 where c+d is an integer of at least 1;

R 5 is H, a C 1 -C 5 alkyl group, or —C(O)—Y—C(O)O − M + ; and

e is an integer of 1 to 40.

2. The coating composition of claim 1 , where the non-fluorinated compound mixture comprises at least one compound selected from an alkali metal salt of poly(meth)acrylic acid, ammonium compound salt of poly(meth)acrylic acid, amine salt of poly(meth)acrylic acid, or mixtures thereof.

3. The coating composition of claim 1 , where the non-fluorinated compound mixture comprises at least one compound selected from an alkali metal salt of hydrolyzed α-olefin/maleic anhydride copolymer, ammonium compound salt of hydrolyzed α-olefin/maleic anhydride copolymer, amine salt of hydrolyzed α-olefin/maleic anhydride copolymer, alkali metal salt of esterified α-olefin/maleic anhydride copolymer, ammonium compound or amine salt of esterified α-olefin/maleic anhydride copolymer, α-olefin/maleic anhydride copolymer amic acid resin, salt of α-olefin/maleic anhydride copolymer amic acid resin, or mixtures thereof.

4. The coating composition of claim 1 , where the non-fluorinated compound mixture further comprises at least one compound selected from a polycarboxylic acid calcium sequestrant or mixture of polycarboxylic acid calcium sequestrants.

5. The coating composition of claim 1 , where the non-fluorinated compound mixture comprises at least one compound from a and at least one compound from c.

6. The coating composition of claim 1 , further comprising a hydrophobic surface effect agent.

7. The coating composition of claim 6 wherein the hydrophobic surface effect agent is selected from the group consisting of hydrophobic non-fluorinated cationic acrylic polymers, hydrophobic non-fluorinated anionic acrylic polymers, hydrophobic non-fluorinated nonionic acrylic polymers, partially fluorinated urethanes, hydrophobic non-fluorinated urethanes, cationic partially fluorinated acrylic polymers or copolymers, nonionic partially fluorinated acrylic polymers or copolymers, partially fluorinated acrylamide polymers or copolymers, fluorinated phosphates, fluorinated ethoxylates, fluorinated or non-fluorinated organosilanes, silicones, waxes, and mixtures thereof.

8. The coating composition of claim 6 , comprising 10 to 90% by weight of the non-fluorinated compound mixture and 10 to 90% by weight of the surface effect agent, based on the total solids weight of the coating composition.

9. The coating composition of claim 8 , comprising 30 to 90% by weight of the non-fluorinated compound mixture and 10 to 70% by weight of the surface effect agent, based on the total solids weight of the coating composition.

10. The coating composition of claim 1 , comprising 30 to 100% by weight of the non-fluorinated compound mixture, based on the total solids weight of the coating composition.

11. An article comprising a substrate coated with a coating composition, where the coating composition comprises 10 to 100% by weight of a non-fluorinated compound mixture, based on the total solids weight of the coating,

where the non-fluorinated compound mixture comprises at least one compound from b, and at least one compound from a or c:

a) an alkali metal salt of poly(meth)acrylic acid, ammonium compound salt of poly(meth)acrylic acid, amine salt of poly(meth)acrylic acid, or mixtures thereof;

b) silicone polyether, alkali metal salt of silicone polyether carboxylate, ammonium compound salt of silicone polyether carboxylate, amine salt of silicone polyether carboxylate, or mixtures thereof;

c) alkali metal salt of hydrolyzed α-olefin/maleic anhydride copolymer, ammonium compound salt of hydrolyzed α-olefin/maleic anhydride copolymer, amine salt of hydrolyzed α-olefin/maleic anhydride copolymer, alkali metal salt of esterified α-olefin/maleic anhydride copolymer, ammonium compound or amine salt of esterified α-olefin/maleic anhydride copolymer, α-olefin/maleic anhydride copolymer amic acid resin, salt of α-olefin/maleic anhydride copolymer amic acid resin, or mixtures thereof;

where the non-fluorinated compound mixture has a pH of about 7 to about 10.5; and

where the at least one compound from b is from formula (I) or (II):

wherein

R 1 , R 2 , and R 3 are independently C 1 -C 8 alkyl groups;

X is a linear or branched C 1 -C 4 alkylene group;

R 4 is independently H or —C(O)—Y—C(O)O − M + ,

Y is a linear or branched, saturated or unsaturated C 1 -C 5 alkylene group;

M is independently H, alkali metal, NH 4 + , dialkyl ammonium cation, or amine cation;

a and b are independently integers of 1 to 40 where a+b is an integer of at least 2; and

c and d are independently integers of 0 to 20 where c+d is an integer of at least 1;

R 5 is H, a C 1 -C 5 alkyl group, or —C(O)—Y—C(O)O − M + , and

e is an integer of 1 to 40.

12. The article of claim 11 , where the substrate is a textile, carpet, unglazed concrete, brick, tile, granite, limestone, marble, grout, mortar, statuary, monument, wood, composite material, terrazzo, gypsum board, wall or ceiling panel, metal, glass, proppant particle, or a combination thereof.

13. The article of claim 11 , where the non-fluorinated compound mixture comprises at least one compound from a and at least one compound from c.

14. The article of claim 11 , further comprising a hydrophobic surface effect agent selected from the group consisting of a fatty acid ester of cyclic or acyclic polyols, fatty esters of polycarboxylic acids, hydrophobic non-fluorinated cationic acrylic polymers, hydrophobic non-fluorinated anionic acrylic polymers, hydrophobic non-fluorinated nonionic acrylic polymers, partially fluorinated urethanes, hydrophobic non-fluorinated urethanes, cationic partially fluorinated acrylic polymers or copolymers, nonionic partially fluorinated acrylic polymers or copolymers, partially fluorinated acrylamide polymers or copolymers, fluorinated or non-fluorinated phosphates, fluorinated ethoxylates, fluorinated or non-fluorinated organosilanes, silicones, waxes, and mixtures thereof.

15. The article of claim 14 , comprising 10 to 90% by weight of the non-fluorinated compound mixture and 10 to 90% by weight of the surface effect agent, based on the total solids weight of the coating composition.

16. The article of claim 11 , comprising 30 to 100% by weight of the non-fluorinated compound mixture, based on the total solids weight of the coating composition.

17. A method of providing a surface effect to a substrate, the method comprising contacting a substrate with a coating composition, where the coating composition comprises 10 to 100% by weight of a non-fluorinated compound mixture, based on the total solids weight of the coating,

where the non-fluorinated compound mixture comprises at least one compound from b, and at least one compound from a or c:

a) an alkali metal salt of poly(meth)acrylic acid, ammonium compound salt of poly(meth)acrylic acid, amine salt of poly(meth)acrylic acid, or mixtures thereof;

b) silicone polyether, alkali metal salt of silicone polyether carboxylate, ammonium compound salt of silicone polyether carboxylate, amine salt of silicone polyether carboxylate, or mixtures thereof;

c) alkali metal salt of hydrolyzed α-olefin/maleic anhydride copolymer, ammonium compound salt of hydrolyzed α-olefin/maleic anhydride copolymer, amine salt of hydrolyzed α-olefin/maleic anhydride copolymer, alkali metal salt of esterified α-olefin/maleic anhydride copolymer, ammonium compound or amine salt of esterified α-olefin/maleic anhydride copolymer, α-olefin/maleic anhydride copolymer amic acid resin, salt of α-olefin/maleic anhydride copolymer amic acid resin, or mixtures thereof;

where the non-fluorinated compound mixture has a pH of about 7 to about 10.5; and

where the at least one compound from b is from formula (I) or (II):

wherein

R 1 , R 2 , and R 3 are independently C 1 -C 8 alkyl groups;

X is a linear or branched C 1 -C 4 alkylene group;

R 4 is independently H or —C(O)—Y—C(O)O − M + ,

Y is a linear or branched, saturated or unsaturated C 1 -C 5 alkylene group;

M is independently H, alkali metal, NH 4 + , dialkyl ammonium cation, or amine cation;

a and b are independently integers of 1 to 40 where a+b is an integer of at least 2; and

c and d are independently integers of 0 to 20 where c+d is an integer of at least 1;

R 5 is H, a C 1 -C 5 alkyl group, or —C(O)—Y—C(O)O − M + , and

e is an integer of 1 to 40.

18. The method of claim 17 , where the contacting step occurs by exhaustion, foam, flex-nip, nip, pad, kiss-roll, beck, skein, winch, liquid injection, overflow flood, roll, brush, roller, spray, dipping or immersion.

19. The method of claim 18 , where the contacting step occurs inside a laundry machine.

20. The method of claim 17 , where 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 release, soil repellency, soil release, water repellency, odor control, antimicrobial, sun protection, or cleanability.

Assignments (2)
PATENT SECURITY AGREEMENT Recorded May 7, 2020
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 052598/0572 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 23, 2019
From: BROWN, GERALD ORONDE; CROSETTO, TESS; KOHLER, EWA; SWOREN, JOHN CHRISTOPHER
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 048971/0317 →
Continuity (2)
Provisional Application 62415543 · Nov 1, 2016
Related Publication 20190256739A1 · Aug 22, 2019