Stain repellent compositions and applications thereof
View Patent ↗The present invention provides fluorinated compounds as well as dispersions of the fluorinated compounds. The fluorinated compounds described herein, in some embodiments, can be applied substrates such as textiles, including carpet and other floor coverings.
1. A fluorinated compound of Formula (I):
wherein Z is a trivalent organic group;
L is a residue of a divalent diol, a diamine, a urea, a dialcohol amine, an 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 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—,
wherein R f is a fluoroalkyl; R a is a direct bond, an 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 an alkyl; X is —O—, —S— or —N(R 2 )—, wherein R 2 is hydrogen or alkyl; and R o is methyl, ethyl, propyl, chlorinated methyl, chlorinated ethyl, chlorinated propyl, —R 3 —O—R 4 ,
or —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 methyl, ethyl, and propyl, and p ranges from 1 to 50.
2. The compound of claim 1 , wherein L is a residue of 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.
3. The fluorinated compound of claim 2 , wherein Z comprises one or more of
4. The fluorinated compound of claim 2 , wherein R f —R a —X— comprises a residue having the formula (C q F 2q+1 )(CH 2 ) u O—, wherein q ranges from 4 to 20, and wherein u ranges from 1 to 20.
5. The fluorinated compound of claim 4 , wherein R f —R a —X— comprises (C 4 F 9 )(CH 2 ) u O—, (C 6 F 13 )(CH 2 ) u O—, (C 8 F 17 )(CH 2 ) u O—, (C 10 F 21 )(CH 2 ) u O—, (C 12 F 25 )(CH 2 ) u O—, 3(C 14 F 28 )(CH 2 ) u O—, (C 16 F 33 )(CH 2 ) u O—, (C 18 F 39 )(CH 2 ) u O—, or (C 20 F 41 )(CH 2 ) u O—, or mixtures thereof.
6. The compound of claim 2 , wherein R o —X— comprises a residue of a monoalkyl ether of a polyethylene glycol or a monoalkyl ether of a polypropylene glycol.
7. The fluorinated compound of claim 2 , wherein R o —X— comprises a residue of a chlorinated alcohol.
8. The fluorinated compound of claim 7 , wherein the chlorinated alcohol comprises 1,3-dichloro-2-propanol, 2,2,2-trichloroethanol or 2,2-dichloroethanol or mixtures thereof.
9. The fluorinated compound of claim 2 , wherein R o is
and R 5 and R 6 independently are methyl, ethyl, or propyl.
10. The fluorinated compound of claim 9 , wherein R 5 is ethyl and R 6 is methyl.
11. The fluorinated compound of claim 10 , wherein p ranges from about 7 to about 33.
12. The fluorinated compound of claim 2 , wherein the compound has a molecular weight ranging from about 8,250 to about 20,000.
13. The fluorinated compound of claim 1 , wherein L comprises a residue of a diamine, a dialcohol amine, or an aminoalcohol.
14. The fluorinated compound of claim 13 , wherein L is selected from ethylenediamine, propylene diamine, butylenediamine, hexamethylene diamine, ethanolamine, aminopropanol, urea, diethanolamine, methyldiethanolamine, phenyldiethanolamine, or a mixture thereof.
15. The fluorinated compound of claim 13 , wherein R f —R a —X— comprises a residue having the formula (C q F 2q+1 )(CH 2 ) u O—, wherein q ranges from 4 to 20 and u ranges from 1 to 20.
16. The compound of claim 13 , wherein R o —X— comprises a residue of a monoalkyl ether of a polyethylene glycol or a monoalkyl ether of a polypropylene glycol.
17. The fluorinated compound of claim 13 , wherein R o —X— comprises a residue of a chlorinated alcohol.
18. The fluorinated compound of claim 13 , wherein R o is
and R 5 and R 6 independently are methyl, ethyl, or propyl, and wherein p ranges from about 7 to about 33.
19. The fluorinated compound of claim 13 , wherein the compound has a molecular weight ranging from about 8,250 to about 20,000.
20. A fluorinated compound of Formula (I):
wherein Z comprises one or more of
L is a residue of 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;
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 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—,
wherein R f is a fluoroalkyl; IV is a direct bond, an 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 an alkyl; X is —O—, —S— or —N(R 2 )—, wherein R 2 is hydrogen or alkyl; and R o is methyl, ethyl, propyl, chlorinated methyl, chlorinated ethyl, chlorinated propyl, —R 3 —O—R 4 ,
—O—R 24 —O—C(O)—R 25 , or wherein 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 compound has a molecular weight ranging from about 8,250 to about 20,000.