Stain repellent compositions and applications thereof

1. An aqueous dispersion comprising:

particles comprising a fluorinated compound, wherein the fluorinated compound comprises

a reaction product of

(i) a polyisocyanate component and

(ii) a diol component comprising ethylene glycol; diethylene glycol; triethylene glycol; tetraethylene glycol; propylene glycol; dipropylene glycol; tripropylene glycol; 1,3-propanediol; 1,3-butanediol; 1,4-butanediol; neopentyl glycol; 1,6-hexanediol; 1,4-cyclohexanediol; or a mixture thereof,

the reaction product further reacted with an organic component comprising

(a) fluorinated molecules having a plurality of fluorinated carbon atoms and at least one isocyanate reactive functionality, and

(b) non-fluorinated molecules of Formula (III):

R o —X—H  (III)

wherein X is —O—, —S— or —N(R 2 )—, and R 2 is hydrogen;

wherein R o is methyl, ethyl, or propyl, —R 3 —O—R 4 ,

 or —O—R 24 —O—C(O)—R 25 , and R 3 , R 4 , R 5 , R 6 , R 24 and R 25 are independently selected from the group consisting of methyl, ethyl, and propyl, and p ranges from 1 to 50

wherein the fluorinated compound has a molecular weight ranging from about 8,250 to about 20,000.

2. The aqueous dispersion of claim 1 , wherein the particles of the fluorinated compound have an average size ranging from about 10 nm to about 400 nm.

3. The aqueous dispersion of claim 1 , wherein the polyisocyanate component comprises trifunctional isocyanate molecules.

4. The aqueous dispersion of claim 1 , wherein the polyisocyanate component comprises one or more of

wherein R 7 , R 8 , R 9 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 and R 23 are independently selected from the group consisting of alkyl, alkenyl, cycloalkyl, and aryl; and

wherein R 10 , R 11 and R 12 are independently selected from the group consisting of hydrogen and alkyl; and

wherein the alkyl, alkenyl, cycloalkyl and aryl of groups of R 7 -R 23 are optionally independently substituted one or more times with a substituent selected from the group consisting of -alkyl, -alkenyl, -fluoroalkyl, -chloroalkyl, bromoalkyl, -aryl, —O-alkyl, —O-alkenyl, —O-aryl, —O-alkylene-aryl, -carboxyl, -hydroxyl, -halo and -nitro.

5. The aqueous dispersion of claim 1 , wherein the fluorinated molecules having a plurality of fluorinated carbon atoms and at least one isocyanate reactive functionality comprise a compound of Formula (II):

R f —R a —X—H  (II)

wherein R is a fluoroalkyl; R a is a direct bond, alkyl, —C m H 2m SO 2 —, —SO 2 N(R 1 )—, or —CON(R 1 )—, wherein m ranges from 1 to 20 and R 1 is hydrogen or alkyl; and X is —O—, —S—, or —N(R 2 )—, wherein R 2 is hydrogen or alkyl.

6. The aqueous dispersion of claim 5 , wherein the compound of Formula (II) comprises a fluorinated alcohol of the formula (C q F 2q+ 1)(CH 2 ) u OH, wherein q ranges from 4 to 20 and u ranges from 1 to 20.

7. The aqueous dispersion of claim 1 , wherein R o is

and R 5 and R 6 independently are methyl, ethyl, or propyl.

8. The aqueous dispersion of claim 7 , wherein R 5 is ethyl and R 6 is methyl.

9. The aqueous dispersion of claim 7 , wherein p ranges from about 7 to about 33.

10. The aqueous dispersion of claim 1 , wherein the organic component further comprises 1,3-dichloro-2-propanol or 2,2-dichloroethanol.

11. An aqueous dispersion comprising:

particles comprising a compound of Formula (I):

wherein Z is a trivalent organic group;

L is a divalent diol, diamine, urea, dialcohol amine, aminoalcohol or a mixture thereof;

n ranges from 1 to 30; and

A 1 , A 2 , A 3 and A 4 are independently selected from

R f —R a —X—; and

R o —X—,

wherein R f is a fluoroalkyl; R a is a direct bond, alkyl, —C m H 2m SO—, —C m H 2m SO 2 —, —SO 2 N(R 1 )—, or —CON(R 1 )—, wherein m ranges from 1 to 20 and R 1 is hydrogen or alkyl; X is —O—, —S— or —N(R 2 )—, wherein R 2 is hydrogen or alkyl; and R o is -alkyl, -alkenyl, -cycloalkyl, -chloroalkyl, -chloroalkenyl, -chlorocycloalkyl, —O-alkyl-glycidyl, —R 3 —O—R 4 ,

 or —O—R 24 —O—C(O)—R 25 , wherein R 3 , R 4 , R 5 , R 6 , R 24 and R 25 are independently selected from the group consisting of alkyl and alkenyl and p ranges from 1 to 50 and wherein the alkyl and alkenyl of R 3 -R 6 , R 24 and R 25 are optionally independently substituted one or more times with a substituent selected from the group consisting of alkyl, alkenyl, and halo, and

wherein at least one of A 1 , A 2 , A 3 and A 4 is R f —R a —X— and at least one of A 1 , A 2 , A 3 and A 4 is R o —X—.

12. The aqueous dispersion of claim 11 , wherein

L is a divalent diol comprising ethylene glycol; diethylene glycol; triethylene glycol; tetraethylene glycol; propylene glycol; dipropylene glycol; tripropylene glycol; 1,3-propanediol; 1,3-butanediol; 1,4-butanediol; neopentyl glycol; 1,6-hexanediol; 1,4-cyclohexanediol; or a mixture thereof;

A 1 , A 2 , A 3 and A 4 are independently selected from

R f —R a —X—; and

R o —X—,

wherein R f is a fluoroalkyl; R a is a direct bond, alkyl, —C m H 2m SO—, —C m H 2m SO 2 —, —SO 2 N(R 1 )—, or —CON(R 1 )—, wherein m ranges from 1 to 20 and R 1 is hydrogen or alkyl; X is —O—, —S— or —N(R 2 )—, wherein R 2 is hydrogen or alkyl; and le is methyl, ethyl, or propyl, —R 3 —O—R 4 ,

 or —O—R 24 —O—C(O)—R 25 , and R 3 , R 4 , R 5 , R 6 , R 24 and R 25 are independently selected from the group consisting of methyl, ethyl, and propyl, and p ranges from 1 to 50.

13. The aqueous dispersion of claim 12 , wherein the particles of the compound of Formula (I) have an average size ranging from about 10 nm to about 400 nm.

14. The aqueous dispersion of claim 12 , wherein R f comprises C q F 2q+1 , wherein q ranges from 4 to 20; R a comprises (CH 2 ) u , wherein u ranges from 1 to 20; and X is O.

15. The aqueous dispersion of claim 12 , wherein for each R f present, q is independently 4, 6, 8, 10, 12, 14, 16, 18, or 20 or mixtures thereof.

16. The aqueous dispersion of claim 12 , wherein R o is

and R 5 and R 6 independently are methyl, ethyl, or propyl.

17. The aqueous dispersion of claim 16 , wherein R 5 is ethyl and R 6 is methyl.

18. The aqueous dispersion of claim 16 , wherein p ranges from about 7 to about 33.

19. The aqueous dispersion of claim 12 , wherein the organic component further comprises 1,3-dichloro-2-propanol or 2,2-dichloroethanol.

20. An aqueous dispersion comprising:

a reaction product of

(i) a polyisocyanate component, and

(ii) a diamine component,

the reaction product further reacted with an organic component comprising

(a) fluorinated molecules having a plurality of fluorinated carbon atoms and at least one isocyanate reactive functionality, and

(b) non-fluorinated molecules of Formula (III):

R o —X—H  (III)

wherein X is —O—, —S— or —N(R 2 )—, and R 2 is hydrogen;

wherein R o is methyl, ethyl, or propyl, —R 3 —O—R 4 ,

 or —O—R 24 —O—C(O)—R 25 , or and R 3 , R 4 , R 5 , R 6 , R 24 and R 25 are independently selected from the group consisting of methyl, ethyl, and propyl, and p ranges from 1 to 50; and

wherein the fluorinated compound has a molecular weight ranging from about 8,250 to about 20,000.