Non-fluorinated urethane based coatings

Patent metadata

Field	Value
Publication number	US-10138392-B2
Application number	US-201414226892-A
Country	US
Kind code	B2
Filing date	Mar 27, 2014
Priority date	Mar 29, 2013
Publication date	Nov 27, 2018
Grant date	Nov 27, 2018

Abstract

A compound for imparting water repellency and optionally stain release to substrates wherein the compound is prepared by (i) reacting (a) at least one isocyanate group-containing compound selected from isocyanate, diisocyanate, polyisocyanate, or mixture thereof, and (b) at least one isocyanate-reactive compound selected from formula (Ia), (Ib), or (Ic):

First claim

What is claimed is:

1. A composition comprising an organic solution or aqueous dispersion of a compound having no unreacted isocyanate groups, said compound prepared by the process comprising:
(i) reacting (a) at least one isocyanate group-containing compound selected from isocyanate, diisocyanate, polyisocyanate, or mixture thereof, and (b) at least one isocyanate-reactive compound selected from formula (Ia) or (Ib):

wherein each R is independently a —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 ) 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;
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 that when the compound is of Formula (Ia) then at least one of R or R 2 is —H and at least two of R are chosen from —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 3 is independently a —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 ) m′ C(O)R 1 ;
each R 4 is independently —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 ;
each n′ is independently 0 to 20;
each m′ is independently 0 to 20;
m′+n′ is greater than 0; and
provided when the compound is Formula (Ib), then the compound is mono-substituted, di-substituted, or tri-substituted with alkyl groups, and at least one R 2 , R 3 or R 4 is a —H.

2. The composition of claim 1 wherein the compounds of formula (Ia) or (Ib) are at least 50% bio-based derived.

3. The composition of claim 1 wherein the compounds of formula (Ia) or (Ib) are 100% bio-based derived.

4. The composition of claim 1 wherein the diioscyanate or polyisocyanate is selected from the group consisting of hexamethylene diisocyanate homopolymer, 3-isocyanatomethyl-3,4,4-trimethylcyclohexyl isocyanate, bis-(4-isocyanatocylohexyl)methane and diisocyanate trimers of formulas (IIa), (IIb), (IIc) and (IId):

5. The composition of claim 1 , wherein step (i) further comprises reacting (c) at least one second compound selected from water, at least one organic compound of Formula (IIIa)
R 5 —X  (IIIa),

at least one organic compound of Formula (IIIb)
R 15 —(OCH 2 CH(OR 16 )CH 2 ) z —OR 17   (IIIb),

or mixtures thereof; wherein
R 5 is selected from a —C 1 to C 30 linear or branched alkyl optionally comprising at least one unsaturated group, a hydroxy-functional C 1 to C 30 linear or branched alkyl, a hydroxy-functional linear or branched C 1 to C 30 polyether, a hydroxy-functional linear or branched polyester, a hydroxy- or amine-functional linear or branched organosiloxane, a thiol-functional C 1 to C 30 linear or branched alkyl, an amine-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;
X is an isocyanate-reactive group selected from —OH, —C(O)OH, —SH, —NH(R 12 ), —O—(CH 2 CH 2 O) s (CH(CH 3 )CH 2 O) t —H

or —[C(O)]—O—(CH 2 CH 2 O) s (CH(CH 3 )CH 2 O) t —H;
R 12 is —H or a monovalent C1 to C6 alkyl group;

R 15 , R 16 , and R 17 are each independently a —H; —R 18 ; —C(O)R 18 provided that at least one R 15 , R 16 , or R 17 is a —H;
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.

6. The composition of claim 5 , wherein the second compound (c) is of Formula (IIIa), and X is —O—(CH 2 CH 2 O) s (CH(CH 3 )CH 2 O) t —H; or —[C(O)]—O—(CH 2 CH 2 O) s (CH(CH 3 )CH 2 O) t —H.

7. The composition of claim 5 , wherein the second compound (c) is of Formula (IIIa),
X is an isocyanate-reactive functional group selected from —OH, —C(O)OH, —SH, —NH(R 12 ); and
R 5 is selected from a —C 1 to C 30 linear or branched alkyl optionally comprising at least one unsaturated group, a hydroxy-functional C 1 to C 30 linear or branched alkyl, a hydroxy-functional linear or branched C 1 to C 30 polyether, a hydroxy-functional linear or branched polyester, a hydroxy-functional linear or branched organosiloxane, a thiol-functional C 1 to C 30 linear or branched alkyl, an amine-functional C 1 to C 30 linear or branched alkyl.

8. The composition of claim 5 , wherein the second compound (c) is of Formula (IIIb).

9. The composition of claim 1 wherein (b) is at least one compound selected from formula (Ia):

wherein R is independently a —H; —R 1 ; or —C(O)R 1 .

10. The composition of claim 1 wherein (b) is at least one compound selected from formula (Ia):

wherein R is independently a —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 .

11. The composition of claim 1 wherein (b) is at least one compound selected from formula (Ib):

12. A method of preparing an organic solution or aqueous composition of a compound having no unreacted isocyanate groups comprising:
(i) reacting (a) at least one isocyanate group-containing compound selected from isocyanate, diisocyanate, polyisocyanate, or mixture thereof, and (b) at least one isocyanate-reactive compound selected from formula (Ia) or (Ib):

wherein each R is independently a —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;
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 that when the compound is of Formula (Ia) then at least one of R or R 2 is —H and at least two of R are chosen from —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 3 is independently a —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 ) m′ C(O)R 1 ;
each R 4 is independently —H, a linear or branched alkyl group having 6 to 30 carbons option

Assignees

• Chemours Co Fc Llc
• Chemours Co Fc Llc

Inventors

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

Classifications

• D06M15/572

  Reaction products of isocyanates with polyesters or polyesteramides · CPC title

• C08G18/281

  Monocarboxylic acid compounds · CPC title

• C08G18/283

  Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds · CPC title

• C08G18/73

  acyclic · CPC title

• Y10T442/2164

  Coating or impregnation specified as water repellent · CPC title