Non-fluorinated urethane based coatings

Patent metadata

Field	Value
Publication number	US-10246608-B2
Application number	US-201514863777-A
Country	US
Kind code	B2
Filing date	Sep 24, 2015
Priority date	Sep 26, 2014
Publication date	Apr 2, 2019
Grant date	Apr 2, 2019

Abstract

The present invention is an aqueous composition comprising 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 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; 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. An aqueous composition comprising at least one hydrophobic compound having at least one linkage of Formula I:
—NHC(O)—X—  (I)

wherein
the linkage of Formula (I) composes 30 to 100% by mol of the total urethane linkages in the hydrophobic compound;
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 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; and
each R 1 is independently a linear or branched alkyl group having 5 to 29 carbons.

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

3. The aqueous composition 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 9 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 one R is a —R 1 ; —C(O)R 1 ;

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 one R or R 4 is a linear or branched alkyl group optionally comprising at least 1 unsaturated bond, or combinations thereof;

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 one R 19 or R is —C(O)R 1 ,

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

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

6. The aqueous composition 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(R12)-C(O)—NH—, —OC(O)NH—, —C(O)NH—, —SC(O)NH—, —O—(CH2CH2O)s(CH(CH3)CH2O)t-C(O)NH—,

or —[C(O)]—O—(CH2CH2O)s(CH(CH3)CH2O)t-C(O)NH—;
X is defined as above;
R6 is selected from a —C1 to C30 linear or branched alkyl optionally comprising at least one unsaturated group, a hydroxy- or urethane-functional C1 to C30 linear or branched alkyl, a hydroxy- or urethane-functional linear or branched C1 to C30 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 aqueous composition of claim 3 wherein X is selected from Formula (IIa) to be Formula (IIa′):

wherein the R variables not directly bonded to NHC(O) are further limited to independently —H; —R 1 ; or —C(O)R 1 .

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

wherein the R variables not directly bonded to NHC(O) are 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 .

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

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

11. The aqueous composition 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 aqueous composition 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 aqueous composition of claim 6 , wherein a linkage of Formula (IVb) is present.

14. The aqueous composition of claim 1 , further comprising inorganic oxide particles.

15. A method of treating a fibrous substrate comprising applying to the surface of the substrate an aqueous composition of claim 1 .

Assignees

• Chemours Co Fc Llc

Inventors

• Sworen John Christopher
• Brown Gerald Oronde
• Vincenzini Mario
• Sparsoe Flemming Vang
• Kohler Ewa

Classifications

• D21H21/16

  Sizing or water-repelling agents · CPC title

• D21H19/26

  Aminoplasts · CPC title

• D21H17/57

  Polyureas; Polyurethanes · CPC title

• D06M2200/12

  Hydrophobic properties · CPC title

• D06M2101/16

  Synthetic fibres, other than mineral fibres · CPC title