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US 5,859,126 AGranted
Coatings containing fluorinated esters
AssigneeE. I. Du Pont de Nemours and Company
InventorsDouglas Robert Anton, Jack Robert Kirchner, William Wesley Bennett, Jr.
Life of this patent
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Abstract
Coating compositions containing an alkyd, urethane or unsaturated polyester resin, and an ester of an unsaturated acid and a fluorinated alcohol wherein the cured coating has an advancing hexadecane contact angle of at least about 40 degrees and durable improved oil and water repellency is disclosed.
Claims8
A coating composition comprising
- A. an ester of an unsaturated acid and a fluorinated alcohol or thiol selected from the group consisting of the Formula 1a, 1b and 2,
- R.sub.f --X--S--OC--R, Formula 1a
- R.sub.f --X--A--OC--R.sub.x --CO--A--X--R.sub.f, Formula 1b ##STR6## wherein:
- R.sub.f is a C.sub.2 -C.sub.20 perfluoroalkyl radical, or a C.sub.5 -C.sub.38 perfluoroalkyl radical having at least one ether oxygen atom;
- R is a C.sub.3 -C.sub.21 unsaturated aliphatic hydrocarbon radical, a C.sub.8 -C.sub.13 aryl radical having at least one non-aromatic double bond, or mixtures thereof;
- X is independently --(CH2).sub.m.sup.-, --CON(R.sub.1)R.sub.2 --, --SO.sub.2 N(R.sub.1)R.sub.2 - or --(OCH.sub.2 CHR.sub.3).sub.b O-, wherein m is 1 to about 20;
- b is 3 to about 15;
- R.sub.1 is H or alkyl radical of 1 to about 4 carbon atoms, R.sub.2 is C.sub.1 -C.sub.12 alkylene, and R.sub.3 is H or CH.sub.2 Cl;
- A is O or S;
- R.sub.x is a divalent C.sub.3 -C.sub.22 unsaturated aliphatic hydrocarbon radical;
- a divalent C.sub.8 -C.sub.13 aryl radical having at least one non-aromatic double bond, or mixtures thereof;
- a is 1 or 2;
- and
- B. an alkyd, Type I urethane or unsaturated polyester resin;
- wherein a cured coating resulting from said coating composition has an advancing hexadecane contact angle of at least about 40 degrees has durable oil and water repellancy.
12 more elements
A cured coating composition comprising:
- A. an ester of an unsaturated acid and a fluorinated alcohol or thiol selected from the group consisting of the Formula 1a, 1b, and 2
- R.sub.f --X--S--OC--R, Formula 1a
- R.sub.f --X--A--OC--R.sub.x --CO--A--X--R.sub.f, Formula 1b ##STR9## wherein:
- R.sub.f is a C.sub.2 -C.sub.20 perfluoroalkyl radical, or a C5-C.sub.38 perfluoroalkyl radical having at least one ether oxygen atom;
- R is a C.sub.3 -C.sub.21 unsaturated aliphatic hydrocarbon radical, a C.sub.8 -C.sub.13 aryl radical having at least one non-aromatic double bond, or mixtures thereof;
- X is independently --(CH.sub.2).sub.m.sup.-, --CON(R.sub.1)R.sub.2 --, --SO.sub.2 N(R.sub.1)R.sub.2 - or --(OCH.sub.2 CHR.sub.3).sub.b O-, wherein m is 1 to about 20;
- b is 3 to about 15;
- R.sub.1 is H or alkyl radical of 1 to about 4 carbon atoms, R.sub.2 is C.sub.1 -C.sub.12 alkylene, and R.sub.3 is H or CH.sub.2 Cl;
- A is O or S;
- R.sub.x is a divalent C.sub.3 -C.sub.22 unsaturated aliphatic hydrocarbon radical;
- a divalent C.sub.8 -C.sub.13 aryl radical having at least one non-aromatic double bond, or mixtures thereof;
- a is 1 or 2,
- and
- B. an alkyd, urethane or unsaturated polyester resin;
- wherein a cured coating resulting from said coating composition has an advancing hexadecane contact angle of at least about 40 degrees.
12 more elements
A method of improving the oil repellency of an alkyd, urethane or unsaturated polyester coating composition comprising adding to said coating composition an effective amount of an ester of an unsaturated acid and a fluorinated alcohol or thiol selected from the group consisting of the Formula 1a, 1b, and 2
- R.sub.f --X--S--OC--R, Formula 1a
- R.sub.f --X--A--OC--R.sub.x --CO--A--X--R.sub.f, Formula 1b ##STR10## wherein:
- R.sub.f is a C.sub.2 -C.sub.20 perfluoroalkyl radical, or a C.sub.5 -C.sub.38 perfluoroalkyl radical having at least one ether oxygen atom;
- R is a C.sub.3 -C.sub.21 unsaturated aliphatic hydrocarbon radical, a C.sub.8 -C.sub.13 aryl radical having at least one non-aromatic double bond, or mixtures thereof;
- X is independently --(CH.sub.2).sub.m.sup.-, --CONR.sub.1 R.sub.2 --, --SO.sub.2 NR.sub.1 R.sub.2 -- or --(OCH.sub.2 CHR.sub.3).sub.b O-, wherein m is 1 to about 20;
- b is 3 to about 15;
- R.sub.1 is H or alkyl radical of 1 to about 4 carbon atoms, R.sub.2 is C.sub.1 -C.sub.12 alkylene, and R.sub.3 is H or CH.sub.2 Cl;
- A is O or S;
- R.sub.x is a divalent C.sub.3 -C.sub.22 unsaturated aliphatic hydrocarbon radical;
- a divalent C.sub.8 -C.sub.13 aryl radical having at least one non-aromatic double bond, or mixtures thereof;
- and
- a is 1 or 2.
9 more elements
Dependencies are inferred from the claim text.