Use of non-fluorinated or partially fluorinated urethanes in coatings

Patent metadata

Field	Value
Publication number	US-9938431-B2
Application number	US-201514863916-A
Country	US
Kind code	B2
Filing date	Sep 24, 2015
Priority date	Sep 26, 2014
Publication date	Apr 10, 2018
Grant date	Apr 10, 2018

Abstract

The present invention is a method for imparting surface effects to a substrate using at least one hydrophobic compound with at least one linkage of Formula I:

—NHC(O)—X—  (I)

wherein X is the residue of a cyclic or acyclic sugar alcohol which is substituted with at least one —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 the cyclic or acyclic sugar alcohol is selected from a saccharide, reduced sugar, aminosaccharide, aldonic acid, or aldonic acid lactone; wherein 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 optionally comprising at least 1 unsaturated bond; and each R 2 is independently —H, a linear or branched alkyl group having 6 to 30 carbons optionally comprising at least 1 unsaturated bond, or mixtures thereof.

First claim

What is claimed is:

1. A method for imparting surface effects to a substrate comprising contacting all or a portion of a surface of the substrate with a coating composition comprising a coating base and at least one hydrophobic compound having at least one linkage of Formula I:
—NHC(O)—X—  (I)

wherein
X is the residue of a cyclic or acyclic sugar alcohol which is 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 the cyclic or acyclic sugar alcohol is selected from a saccharide, reduced sugar, aminosaccharide, aldonic acid, or aldonic acid lactone; wherein

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 optionally comprising at least 1 unsaturated bond; and
each R 2 is independently —H, a linear or branched alkyl group having 6 to 30 carbons optionally comprising at least 1 unsaturated bond, or mixtures thereof; and
wherein the hydrophobic compound has no unreacted isocyanate groups.

2. The method of claim 1 , where X is 100% bio-based derived.

3. The method of claim 1 , where X is selected from Formulas (IIa), (IIb), or (IIc):

wherein each R is independently a direct bond to NHC(O) of Formula I; —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 optionally comprising at least 1 unsaturated bond;
each R 2 is independently —H, or a linear or branched alkyl group having 6 to 30 carbons optionally comprising at least 1 unsaturated bond; or a mixtures thereof,
provided when X is Formula (IIa), then at least one R is a direct bond to NHC(O) of Formula 1; 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 ;
each R 4 is independently a direct bond to NHC(O) of Formula I; —H, a linear or branched alkyl group having 6 to 30 carbons optionally comprising at least 1 unsaturated bond, or combinations thereof; —(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 ;
provided when X is Formula (IIb), then at least one R or R 4 is a direct bond to NHC(O) of Formula 1; and at least two R or R 4 are a linear or branched alkyl group optionally comprising at least 1 unsaturated bond, or combinations thereof; —(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 ; and
each R 19 is a direct bond to NHC(O) of Formula I; —H, —C(O)R 1 , or —CH 2 C[CH 2 OR] 3 ,
provided when X is Formula (IIc), then at least one R 19 or R is a direct bond to NHC(O) of Formula I; and at least two R 19 or R are —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 .

4. The method of claim 1 , wherein the hydrophobic compound further comprises at least one moiety Q to form Formula (I′):
-Q-NHC(O)—X—  (I′)

where Q is a monovalent, divalent, or polyvalent moiety selected from linear or branched, cyclic or acyclic, alkylene groups optionally containing at least one group selected from alkoxy, phenyl, siloxane, urethane, urea, biuret, uretdione, cyclized isocyanate, allophanate, or isocyanurate.

5. The method of claim 4 , wherein Q is selected from Formulas (IIIa), (IIIb), (IIIc) and (IIId):

6. The method of claim 1 , wherein the hydrophobic compound further comprises at least one linkage selected from Formulas (IVa), (IVb), (IVc), or mixtures thereof:
R 6 -D  (IVa),

R 15 —(OCH 2 CH(OR 16 )CH 2 ) z —OR 17   (IVb),

—NH—C(O)—NH—X  (IVc)

wherein D is selected from —N(R 12 )—C(O)—NH—, —OC(O)NH—, —C(O)NH—, —SC(O)NH—, —O—(CH 2 CH 2 O) s (CH(CH 3 )CH 2 O) t —C(O)NH—, or —[C(O)]—O—(CH 2 CH 2 O) s (CH(CH 3 )CH 2 O) t —C(O)NH—;
X is defined as above;
R 6 is selected from a —C 1 to C 30 linear or branched alkyl optionally comprising at least one unsaturated group, a hydroxy- or urethane-functional C 1 to C 30 linear or branched alkyl, a hydroxy- or urethane-functional linear or branched C 1 to C 30 polyether, a hydroxy- or urethane-functional linear or branched polyester having a polyester polymer backbone, a hydroxy- or urethane-functional linear or branched organosiloxane, an amine- or urea-functional linear or branched organosiloxane, a thiol- or thiocarbonate functional C 1 to C 30 linear or branched alkyl, an amine- or urea-functional C 1 to C 30 linear or branched alkyl,

wherein
R 7 , R 8 , and R 9 are each independently, —H, —C 1 to C 6 alkyl, or combinations thereof;
R 10 is a divalent alkyl group of 1 to 20 carbons;
R 12 is —H or a monovalent C 1 to C 6 alkyl group;
R 15 , R 16 , and R 17 are each independently a —H; —C(O)NH—, —R 18 ; —C(O)R 18 provided that at least one R 15 , R 16 , or R 17 is a —C(O)NH—;
R 18 is independently a linear or branched alkyl group having 5 to 29 carbons optionally comprising at least 1 unsaturated bond;
z is 1 to 15;
Y is Cl;
s is an integer of 0 to 50;
t is an integer of 0 to 50; and
s+t is greater than 0.

7. The method of claim 3 wherein X is selected from Formula (IIa) to be Formula (IIa′):

wherein R is further limited to independently a direct bond to NHC(O), —H; —R 1 ; or —C(O)R 1 .

8. The method of claim 3 wherein X is selected from Formula (IIa) to be Formula (IIa′):

wherein R is further limited to independently a direct bond to
NHC(O), —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 .

9. The method of claim 1 wherein X is selected from Formula (IIb).

10. The method of claim 1 wherein X is selected from Formula (IIc).

11. The method of claim 6 , wherein a linkage of Formula (IVa) is present, and D is —O—(CH 2 CH 2 O) s (CH(CH 3 )CH 2 O) t —C(O)NH—, or —[C(O)]—O—(CH 2 CH 2 O) s (CH(CH 3 )CH 2 O) t —C(O)NH—.

12. The method of claim 6 , wherein a linkage of Formula (IVa) is present,
D is —N(R 12 )—C(O)—NH—, —OC(O)NH—, —C(O)NH—, or —SC(O)NH—; and
R 6 is selected from a —C 1 to C 30 linear or branched alkyl optionally comprising at least one unsaturated group, a hydroxy- or urethane-functional C 1 to C 30 linear or branched alkyl, a hydroxy- or urethane-functional linear or branched C 1 to C 30 polyether, a hydroxy- or urethane-functional linear or branched polyester having a polyester polymer backbone, a hydroxy- or urethane-functional linear or branched organosiloxane, an amine- or urea-functional linear or branched organosiloxane, a thiol- or thiocarbonate functional C 1 to C 30 linear or branched alkyl, or an amine- or urea-functional C 1 to C 30 linear or branched alkyl.

13. The method of

Assignees

• Chemours Co Fc Llc
• Chemours Co Fc Llc

Inventors

• Sworen John Christopher
• Brown Gerald Oronde
• Haidzinskaya Tatsiana
• Kohler Ewa

Classifications

• C09D175/04 Primary

  Polyurethanes · CPC title

• C09D175/06

  from polyesters · CPC title

• C08G18/3221

  hydroxylated esters of carboxylic acids other than higher fatty acids · CPC title

• C08G18/7831 Primary

  containing biuret groups · CPC title

• C09D175/08 Primary

  from polyethers · CPC title