Compositions for surface treatments

Patent metadata

Field	Value
Publication number	US-9988536-B2
Application number	US-201414531193-A
Country	US
Kind code	B2
Filing date	Nov 3, 2014
Priority date	Nov 5, 2013
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

A composition having at least one first component containing a perfluorinated aliphatic structure in which no more than six fluorine bearing carbons are connected in any single straight chain segment, in addition a group providing binding functionality to a surface to be treated or containing at least one polymerisable double bond or containing at least one cross-linkable group, and in addition a divalent radical containing at least one group capable of forming polar interactions or hydrogen bonds, and at least one second component containing a perfluorinated aliphatic structure in which no more than six fluorine bearing carbons are connected in any single straight chain segment and a moiety containing at least one group providing binding functionality to a surface to be treated or containing at least one polymerisable double bond or containing at least one cross-linkable group.

First claim

The invention claimed is:

1. A composition comprising;
a) at least a first compound of Formula A
X-(L1)n-R′-(L2)m-Rf

in which
n is either 0 or 1;
m is either 0 or 1;
Rf is a perfluorinated aliphatic structure, branched, linear or cyclic, in which no more than six fluorine bearing carbons are connected in any single straight chain segment, this structure optionally being interrupted by one or more oxygen atoms;
X being either:
i) a moiety containing at least one group providing binding functionality to a surface to be treated, or containing at least one polymerisable double bond, or containing at least one cross-linkable group; or
ii) an acrylate, a methacrylate, or a vinyl group;

R′ being either:
(i) a divalent radical containing at least one group capable of forming polar interactions or hydrogen bonds; or
(ii) —(CH2)pCH(OH)(CH2)q—, —(CH2)pCH(CH2OH)(CH2)q—, —NR1SO2—, —C(O)NR2— or —C(O)O—,
wherein p and q are independently integers from 1 to 4, and
R1, R2 independently represent a hydrogen atom or an alkyl group that is linear or branched, having from one to four carbon atoms;

L1 and L2 are either:
(i) independently divalent linking radicals which do not form polar interactions or hydrogen bonds, or
(ii) independently divalent linear or branched alkyl chains of up to six carbon atoms,

and

b) a second compound of Formula B
X-(L3)p-Rf
in which
p is either 0 or 1;
Rf is a perfluorinated aliphatic structure, branched, linear or cyclic, in which no more than six fluorine bearing carbons are connected in any single straight chain segment, this structure optionally being interrupted by one or more oxygen atoms;
X being either:
i) a moiety containing at least one group providing binding functionality to a surface to be treated, or containing at least one polymerisable double bond, or containing at least one cross-linkable group; or
ii) an acrylate, a methacrylate, or a vinyl group;

L3 is either:
i) a divalent linking radical which does not form polar interactions or hydrogen bonds, or
ii) a divalent linear or branched alkyl chain of up to six carbon atoms,

wherein Rf is C6F13—, (CF3)2CF(CF2)4— or F(CF(CF3)CF2O)nCF(CF3)— wherein n is 1 to 4.

2. A composition comprising;
a) at least a first compound of Formula A, and
b) a second compound of Formula B
X-(L3)p-Rf
in which
p is either 0 or 1;
Rf is a perfluorinated aliphatic structure, branched, linear or cyclic, in which no more than six fluorine bearing carbons are connected in any single straight chain segment, this structure optionally being interrupted by one or more oxygen atoms;
X being either:
i) a moiety containing at least one group providing binding functionality to a surface to be treated, or containing at least one polymerisable double bond, or containing at least one cross-linkable group; or
ii) an acrylate, a methacrylate, or a vinyl group;

L3 is either:
i) a divalent linking radical which does not form polar interactions or hydrogen bonds, or
ii) a divalent linear or branched alkyl chain of up to six carbon atoms,

wherein the compounds of Formula A are selected from the group consisting of:
a) N-methyl-N-[(2-methylpropenoyl) ethyl]-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylsulfonamide;
b) N-methyl-N-[(propenoyl)ethyl]-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylsulfonamide;
c) propenoic acid, 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-hydroxy nonylester;
d) 2-Methylpropenoic acid, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-2-hydroxy nonylester;
e) 2-(2-methylpropenoy)ethyl-2-(poly[oxy(hexafluoropropene)])-tetrafluoropropanoate;
f) 2-(Propenoy)ethyl-2-(poly[oxy(hexafluoropropene)])-tetrafluoropropanoate;
g) 2-Methylpropenoic acid, 4,4,5,5,6,6,7,7,8,9,9,9-dodecafluoro-2-hydroxy-8-(trifluoromethyl)-nonyl ester;
h) Propenoic acid, 4,4,5,5,6,6,7,7,8,9,9,9-dodecafluoro-2-hydroxy-8-(trifluoromethyl)-nonyl ester;
i) 2-Methylpropenoic acid, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-(hydroxymethyl)octyl ester and
j) Propenoic acid, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-(hydroxymethyl)octyl ester.

3. A composition comprising;
a) at least a first compound of Formula A
X-(L1)n-R′-(L2)m-Rf

in which
n is either 0 or 1;
m is either 0 or 1;
Rf is a perfluorinated aliphatic structure, branched, linear or cyclic, in which no more than six fluorine bearing carbons are connected in any single straight chain segment, this structure optionally being interrupted by one or more oxygen atoms;
X being either:
i) a moiety containing at least one group providing binding functionality to a surface to be treated, or containing at least one polymerisable double bond, or containing at least one cross-linkable group; or
ii) an acrylate, a methacrylate, or a vinyl group;

R′ being either:
(i) a divalent radical containing at least one group capable of forming polar interactions or hydrogen bonds; or
(ii) —(CH2)pCH(OH)(CH2)q—, —(CH2)pCH(CH2OH)(CH2)q—, —NR1SO2—, —C(O)NR2— or —C(O)O—,
wherein p and q are independently integers from 1 to 4, and
R1, R2 independently represent a hydrogen atom or an alkyl group that is linear or branched, having from one to four carbon atoms;

L1 and L2 are either:
(i) independently divalent linking radicals which do not form polar interactions or hydrogen bonds, or
(ii) independently divalent linear or branched alkyl chains of up to six carbon atoms,

and

b) a second compound of Formula B
wherein the compound of Formula B is selected from the group consisting of 2-methylpropenoic acid, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl ester and propenoic acid, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl ester.

4. The composition of any one of the preceding claims, wherein the first compound of Formula A and the second compound of Formula B are respectively in a mole ratio of between 80:20 and 20:80.

5. A substrate having a coating comprising a composition of any one of claims 1 , 2 , or 3 , wherein the substrate comprises fibers selected from the group consisting of plexifilamentary high-density polyolefin; melt-spun polyolefin; melt-spun polyester; melt-blown polyolefin; melt-blown polyester; spun-laced blend of cellulose and polyester; a blend of meta-aramid, para-aramid, viscose and wool; a blend of para-aramid floc and meta-aramid fibrids; polyimide and combinations thereof.

Assignees

• Du Pont

Inventors

• Huebsch Eric
• Brabbs Noel Stephen

Classifications

• Y10T428/2969

  Polyamide, polyimide or polyester · CPC title

• Y10T428/2967

  Synthetic resin or polymer · CPC title

• Y10T428/2965

  Cellulosic · CPC title

• C09D133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08F220/24

  containing perhaloalkyl radicals · CPC title