US4595628A
Expired / Lapsed
US
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Soil repellent fluorinated esters of multi-ring anhydride systems
Assignee: CNA Holdings LLC
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Filing: 1984-07-30
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Granted: 1986-06-17
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Expires: 2004-07-30
Abstract
Abstract Fluorinated esters based on multi-ring anhydride systems are disclosed which have excellent anti-soiling properties, durability and resistance to laundering. The compounds are represented by the formula ##STR1## wherein n is 2 or 3, Q is a linking group such as --CO--, --O--, or (C a H 2a+2-n --(O 2 C) n , R f is a fluorinated radical, and R is derived from an epoxide such as ethylene oxide or epichlorohydrin. Also disclosed are polyester and nylon fibers having these compounds incorporated therein, and a process for producing such soil-repellent fibers.
Inventors
- 👤 Michael G. Kelly
- 👤 Willi R. Steckelberg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 22:05
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/76; C07C67/00; C07C67/24; C07C67/26; D; D06; D06M; D06M13/00; D06M13/10; D06M13/184; D06M13/207; D06M13/21; D06M13/213; Y; Y10; Y10S; Y10S8/00; Y10S8/04; Y10S8/21; Y10T; Y10T428/00; Y10T428/29; Y10T428/2913; Y10T428/2933; Y10T428/2938; Y10T428/2964; Y10T428/2967; Y10T428/2969; Y10T442/00; Y10T442/20; Y10T442/2279; Y10T442/2287
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
208 words
A compound of the formula ##STR22## wherein n is 2 or 3; Q has a valence equal to n and is selected from the group consisting of, (C a H 2a+2-n )(O 2 C) n , --CO(OCH 2 CH 2 ) b O 2 C--, --CO 2 C 6 H 4 O 2 C--, and (CH 3 ) 2 C(C 6 H 4 O 2 C) 2 , wherein a is 2 to 6, b is 2 to 10, and n is as defined above but cannot exceed a; R is selected from --CH 2 CH(R 1 )OH, --CH 2 CH(R 1 )OCH 2 CH(R 1 )OH, --CH 2 CH(OH)CH 2 X, or --CH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 X wherein R 1 is hydrogen or methyl and X is chloro, bromo, hydroxy, or cyano; and R f is a fluorinated radical of the formula --W(C d F 2d )Y wherein W has from 1 to 10 carbon atoms and is selected from alkylene and W'--Z--(W") e where W' and W" are alkylene, Z is O, S, NHCO, or NHSO 2 , and e is 0 or 1, Y is hydrogen, fluoro, or perfluoroalkoxy of 1 to 6 carbon atoms, and d is 2 to 20.
Claim 2
Dependent Claim
208 words
A compound of the formula ##STR22## wherein n is 2 or 3; Q has a valence equal to n and is selected from the group consisting of, (C a H 2a+2-n )(O 2 C) n , --CO(OCH 2 CH 2 ) b O 2 C--, --CO 2 C 6 H 4 O 2 C--, and (CH 3 ) 2 C(C 6 H 4 O 2 C) 2 , wherein a is 2 to 6, b is 2 to 10, and n is as defined above but cannot exceed a; R is selected from --CH 2 CH(R 1 )OH, --CH 2 CH(R 1 )OCH 2 CH(R 1 )OH, --CH 2 CH(OH)CH 2 X, or --CH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 X wherein R 1 is hydrogen or methyl and X is chloro, bromo, hydroxy, or cyano; and R f is a fluorinated radical of the formula --W(C d F 2d )Y wherein W has from 1 to 10 carbon atoms and is selected from alkylene and W'--Z--(W") e where W' and W" are alkylene, Z is O, S, NHCO, or NHSO 2 , and e is 0 or 1, Y is hydrogen, fluoro, or perfluoroalkoxy of 1 to 6 carbon atoms, and d is 2 to 20.
Claim 3
Dependent Claim
82 words
A compound according to claim 1 wherein Q is selected from --CO 2 (CH 2 ) a O 2 C--, --CO(OCH 2 CH 2 ) b O 2 C--, --CO 2 CH(CH 2 O 2 C)2, CH 3 C(CH 2 O 2 C) 3 , CH 3 CH 2 C(CH 2 O 2 C) 3 , C 4 , --CO 2 C 6 H 4 O 2 C--, and (CH 3 ) 2 C(C 6 H 4 O 2 C) 2 .
Claim 4
Dependent Claim
30 words
A compound according to claim 2 wherein Q is independently located at the 4 or 5 position of each benzene ring with respect to the --CO 2 R f moiety.
Claim 5
Dependent Claim
45 words
A compound according to claim 3 wherein W is alkylene of 2 to 6 carbon atoms, d is 2 to 12, and R is --CH 2 CH 2 OH, --CH 2 CH(OH)CH 2 Cl, --CH 2 CH(OH)CH 2 OH, or --CH 2 CH(OH)CH 2 Br.
Claim 6
Dependent Claim
47 words
A compound according to claim 4 wherein R f is selected from --CH 2 CH 2 (CF 2 ) g CF 3 or --CH 2 CH 2 (CF 2 ) h OCF(CF 3 ) 2 wherein g is 5 to 11 and h is 2 to 12.
Claim 7
Dependent Claim
30 words
A compound according to claim 5 wherein R f is --CH 2 CH 2 (CF 2 CF 2 ) j CF 2 CF 3 and j is 2 to 5.
Claim 8
Dependent Claim
20 words
A compound according to claim 6 wherein R is --CH 2 CH 2 OH or --CH 2 CH(OH)CH 2 Cl.
Claim 9
Dependent Claim
10 words
A compound according to claim 5 having the formula ##STR23##
Claim 10
Dependent Claim
16 words
A compound according to claim 5 having the formula ##STR24## wherein b is 2 to 6.
Claim 11
Dependent Claim
10 words
A compound according to claim 5 having the formula ##STR25##
Claim 12
Dependent Claim
151 words
A compound of the formula ##STR26## wherein n is 2 or 3; P(O) n is the residue of an organic polyol P(OH) n having 2-20 carbon atoms wherein n is as defined above; R is selected from --CH 2 CH(R 1 )OH, --CH 2 CH(R 1 )OCH 2 CH(R 1 )OH, --CH 2 CH(OH)CH 2 X, or --CH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 wherein R 1 is hydrogen or methyl and X is chloro, bromo, hydroxy, or cyano; and R f is a fluorinated radical of the formula --W(C d F 2d )Y wherein W has from 1 to 10 carbon atoms and is selected from alkylene and W'--Z--(W") e where W' and W" are alkylene, Z is O, S, NHCO, or NHSO 2 , and e is 0 or 1, Y is hydrogen, fluoro, or perfluoroalkoxy of 1 to 6 carbon atoms, and d is 2 to 20.
Claim 13
Dependent Claim
151 words
A compound of the formula ##STR26## wherein n is 2 or 3; P(O) n is the residue of an organic polyol P(OH) n having 2-20 carbon atoms wherein n is as defined above; R is selected from --CH 2 CH(R 1 )OH, --CH 2 CH(R 1 )OCH 2 CH(R 1 )OH, --CH 2 CH(OH)CH 2 X, or --CH 2 CH(OH)CH 2 OCH 2 CH(OH)CH 2 wherein R 1 is hydrogen or methyl and X is chloro, bromo, hydroxy, or cyano; and R f is a fluorinated radical of the formula --W(C d F 2d )Y wherein W has from 1 to 10 carbon atoms and is selected from alkylene and W'--Z--(W") e where W' and W" are alkylene, Z is O, S, NHCO, or NHSO 2 , and e is 0 or 1, Y is hydrogen, fluoro, or perfluoroalkoxy of 1 to 6 carbon atoms, and d is 2 to 20.
Claim 14
Dependent Claim
72 words
A compound of claim 11 wherein P(O) n is selected from --O(CH 2 ) a O--, --(OCH 2 CH 2 ) b O--, --OCH(CH 2 O) 2 , CH 3 C(CH 2 O) 3 , CH 3 CH 2 C(CH 2 O) 3 , --OC 6 H 4 O-- and (CH 3 ) 2 C(C 6 H 4 O) 2 wherein a is 2 to 6 and b is 2 to 10.
Claim 15
Dependent Claim
45 words
A compound according to claim 12 wherein W is alkylene of 2 to 12 carbon atoms, d is 2 to 12, and R is --CH 2 CH 2 OH, --CH 2 CH(OH)CH 2 Cl, --CH 2 CH(OH)CH 2 OH, or --CH 2 CH(OH)CH 2 Br.
Claim 16
Dependent Claim
47 words
A compound according to claim 13 wherein R f is selected from --CH 2 CH 2 (CF 2 ) g CF 3 or --CH 2 CH 2 (CF 2 ) h OCF(CF 3 ) 2 wherein g is 5 to 11 and h is 2 to 12.
Claim 17
Dependent Claim
25 words
A polyester or polyamide fiber having incorporated therewith a compound of claim 1 or 11 in an amount sufficient to impart oil or water repellency.
Claim 18
Dependent Claim
61 words
A process of incorporating a compound of claim 1 into the surface of a polyester or polyamide fiber which comprises contacting said compound in liquid medium with said fiber and thereafter annealing the resulting fiber at elevated temperature, the amount of said compound and the time and temperature of annealing being sufficient to impart oil or water repellency to said fiber.
References Cited (Backward Citations)
US4063024A
Cited
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