Fluoroalkyloxy dispersant

Details Fluoroalkyloxy dispersant Fluoroalkyloxy dispersant

2000-06-28

2002-09-17

Metzmaier, Daniel S. (Department: 1712)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C560S024000, C560S047000, C560S125000, C560S157000, C560S172000, C560S183000, C516S030000, C252S182150

Reexamination Certificate

active

06452038

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to a compound useful as a dispersant in highly fluorinated solvents. The compound contains an ethylenic double bond by which it may be joined to another moiety, e.g. by free-radical polymerization. The compound is described by the formula: CH
2
═C(R
1
)—(O)O—R
6
—NHCO
2
(CH
2
)
p
(CF
2
)
q
—O—((CF
2
)
a
CFXO)
m
(CF
2
)
r
—Z wherein each R
1
is independently selected from —H, —CH
3
, —F and —Cl, wherein each R
6
is independently selected from substituted or unsubstituted C1-C10 alkyl, cyclic alkyl, or aryl groups, wherein each a is independently selected from 0-3, wherein each X is independently selected from —F, —CF
3
or —CF
2
CF
3
, wherein each p is independently selected from 1-4, each q is independently selected from 1-5, each r is independently selected from 1-5, each m is independently selected from 1-50, each Z is independently selected from —F and —(CH
2
)
s
OH, and each s is independently selected from 1-4.
BACKGROUND OF THE INVENTION
U.S. Pat. No. 5,397,669 (Minnesota Mining & Manufacturing) discloses liquid toners for use with perfluorinated solvents. The patent discloses that the compositions are film-forming, allowing them to function properly as toners. ('669 at p. 8 Ins. 3-5). The '669 patent discloses pigment particles bound to a polymer that is highly fluorinated in specific parts, and that includes monomer units having groups that bind polyvalent metal ions. The '669 patent also discloses pigment particles bound to a polymer that is highly fluorinated in its entirety, without requiring monomers having groups that bind polyvalent metal ions.
U.S. Pat. No. 5,530,053 (Minnesota Mining & Manufacturing) also discloses liquid toners for use with perfluorinated solvents. The toners of '053 are polymeric dyes which are highly fluorinated in specified parts and have attached chromophoric groups. The '053 patent discloses that the toner can form a latex in perfluorinated solvent, where the toner takes a core-shell form with the hydrocarbon portion in the core and the fluorocarbon portion in the shell.
U.S. Pat. No. 5,919,293 (Hewlett-Packard) discloses ink jet inks composed of colorants in Fluorinert™ solvents (Minnesota Mining & Manufacturing Co., St. Paul, Minn.), which are perfluorinated or nearly-perfluorinated alkanes.
U.S. Pat. No. 5,573,711 (Copytele) discloses the use of certain polymeric fluorosurfactants in electrophoretic image displays. The '711 patent teaches the use of Fluorad™ surfactants (Minnesota Mining & Manufacturing Co., St. Paul, Minn.), including FC-171, having the structure R
f
—SO
2
N(C
2
H
5
)(CH
3
CH
3
O)
n
CH
3
, where n is about 8 and R
f
is a fluorocarbon portion.
SUMMARY OF THE INVENTION
Briefly, the present invention provides a compound according to the formula: CH
2
═(R
1
)—C(O)O—R
6
—NHCO
2
(CH
2
)
p
(CF
2
)
q
—O—((CF
2
)
a
CFXO)
m
(CF
2
)
r
—Z, wherein each R
1
is independently selected from —H, —CH
3
, —F and —Cl, wherein each R
6
is independently selected from substituted or unsubstituted C1-C10 alkyl, cyclic alkyl, or aryl groups, wherein each a is independently selected from 0-3, wherein each X is independently selected from —F, —CF
3
or —CF
2
CF
3
, wherein each p is independently selected from 1-4, each q is independently selected from 1-5, each r is independently selected from 1-5, each m is independently selected from 1-50, each Z is independently selected from —F and —(CH
2
)
s
OH, and each s is independently selected from 1-4. Preferably each m is independently selected from 7-15. Preferably Z is —(CH
2
)
s
OH. Preferably a, p, q, r and s are each 1 and wherein X is —F.
In another aspect, the present invention provides a second compound which is a reaction product of the compound above resulting from free-radical addition to the ethylenic double bond. In particular, a non-film-forming latex of particles comprising the compound above in a highly fluorinated solvent is provided.
What has not been described in the art, and is provided by the present invention, is a reactive dispersant according to the present formula and its use in a non-film-forming latex of hydrocarbon/fluorocarbon particles dispersed in a fluorocarbon solvent useful in an electrophoretic display.
In this application:
“reacting dyes” means dyes which are covalently bound to the polymer;
“non-reacting dyes” means dyes which are not substantially incorporated into a polymer by polymerization, including every dye that is not a reacting dye;
“highly fluorinated”, means containing fluorine in an amount of 40 wt % or more, but preferably 50 wt % or more and more preferably 60 wt % or more, and refers to the fluorine content of a population of chemical moieties where applicable, such as in the term, “one or more highly fluorinated macromers”;
“non-fluorinated”, means containing substantially no fluorine, i.e. containing fluorine in an amount of 5 wt % or less, but preferably 1 wt % or less and most preferably 0 wt %, and refers to the fluorine content of a population of chemical moieties where applicable, such as in the term, “one or more non-fluorinated free-radically-polymerizable monomers”;
“C(number)” refers to a chemical moiety containing the indicated number of carbon atoms;
“(meth)acrylate” means acrylate and methacrylate; and
“substituted” means, for a chemical species, substituted by conventional substituents which do not interfere with the desired product or process, e.g., substituents can be alkyl, alkoxy, aryl, phenyl, halo (F, Cl, Br, I), cyano, etc.
It is an advantage of the present invention to provide a dispersant for use in highly fluorinated solvents and which is particularly useful in making a latex of non-film-forming dye-bearing particles.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The present invention provides a compound according to the formula: CH
2
C(R
1
)—C(O)O—R
6
—NHCO
2
(CH
2
)
p
(CF
2
)
q
—O—((CF
2
)
n
CFXO)
m
(CF
2
)
r
(CH
2
)
s
OH, wherein each R
1
is independently selected from —H, —CH, —F and —Cl, wherein each R
6
is independently selected from substituted or unsubstituted C1-C10 alkyl, cyclic alkyl, or aryl groups, wherein each a is independently selected from 0-3, wherein each X is independently selected from —F, —CF
3
or —CF
2
CF
3
, wherein each p is independently selected from 1-4, each q is independently selected from 1-5, each r is independently selected from 1-4, each s is independently selected from 1-4, each m is independently selected from 1-50. Preferably each m is independently selected from 7-15. Preferably a, p, q, r and s are each 1 and wherein X is —F.
A non-film-forming latex employing the dispersant according to the present invention comprises a highly fluorinated liquid solvent and dispersed particles comprising a polymer comprising units according to formula I:
wherein each (fcp) is independently selected from highly fluorinated polymer chains which may terminate at the —A═ group of another unit according to formula I so as to form a polymer molecule that contains two or more A groups linked by (fcp) groups; wherein each Q is independently selected from —H and straight or branched non-fluorinated polymer chains (hcp), wherein no more than one Q of each unit according to formula I may be —H, and wherein each (hcp) may terminate at the —A═ group of another unit according to formula I so as to form a polymer molecule that contains two or more A groups linked by (hcp) groups. Preferably some of the (hcp) groups are branched due to the inclusion of polyfunctional crosslinkers. Preferably the particles contain reacting or non-reacting dyes. Preferably the particles additionally contain charging agents.
Preferably the —A═ group is the moiety according to formula II:
wherein each R
1
is independently selected from —H, —CH
3
, —F and —Cl; wherein each —R
6
— is independently selected from divalent substituted or unsubstituted C1-C10 alkylene, cyclic alkylene, or arylene groups. The (fcp) moieties may terminate at A groups at one or both ends. The (hcp) moieties may terminate at A groups at one or bot

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