Dispersibility improver for fluororesin powders, and organic...

Details Dispersibility improver for fluororesin powders, and organic... Dispersibility improver for fluororesin powders, and organic...

1999-06-30

2001-10-02

Dawson, Robert (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

At least one aryl ring which is part of a fused or bridged...

C524S261000, C524S265000, C524S266000, C524S267000, C524S268000, C524S462000, C524S545000, C524S568000, C528S025000, C528S026000, C528S029000, C528S031000, C528S042000, C556S454000, C556S457000

Reexamination Certificate

active

06297303

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to a polydiorganosiloxane dispersibility improver for fluororesin powders; an organic resin modifier comprising the polydiorganosiloxane dispersibility improver and fluororesin powder and to organic resin compositions that contain the polydiorganosiloxane dispersibility improver.
BACKGROUND OF THE INVENTION
The admixture of a fluororesin powder, e.g., Teflon™ powder, into organic resins is an already known strategy for improving the physical properties of organic resins. For example, Japanese Laid Open (Kokai or Unexamined) Patent Application Number Hei 9-286911 (286,911/1997) teaches the preparation of a highly impact-resistant polycarbonate resin composition by the addition of fibrillar polytetrafluoroethylene powder to polycarbonate resin. However, since fluororesin powders generally have low surface tensions, it has been quite difficult to achieve homogeneous dispersions of fluororesin powders in high surface tension organic resins. As a result, there has been desire for the appearance of a method for inducing the homogeneous dispersion of fluororesin powders in organic resins.
It is an object of this invention is to provide a polydiorganosiloxane dispersibility improver for fluororesin powders that has the ability to induce the uniform dispersion of fluororesin powders in organic resins.
Another object of this invention is to provide a organic resin modifier suitable for modifying the water and oil repellency of organic resin surfaces wherein the organic resin modifier comprises a blend of the polydiorganosiloxane dispersibility improver and fluororesin powder.
Another object of the present invention is to provide organic resin compositions that contain the dispersibility improver and as a consequence have the ability to form uniform and transparent coatings that have an excellent surface lubricity.
SUMMARY OF THE INVENTION
This invention relates to a polydiorganosiloxane dispersibility improver for fluororesin powders, wherein the polydiorganosiloxane contains in pendant position (A) at least one organic group selected from the group consisting of polyoxyalkylene-functional organic groups, alkyl groups having at least 12 carbon atoms, and polydialkylsiloxane chain-containing organic groups, and contains in pendant position or molecular chain terminal position,
(B) at least one perfluoroalkyl-functional organic group with the general formula F(CF
2
)
a
—R
1
— in which R
1
is alkylene or alkyleneoxyalkylene and a is an integer with a value of at least 3.
This invention also pertains to an organic resin modifier comprising a fluororesin powder and the polydiorganosiloxane dispersibility improver. This invention also relates to organic resin compositions that contain the polydiorganosiloxane dispersibility improver.
DETAILED DESCRIPTION OF THE INVENTION
The polydiorganosiloxane dispersibility improver contains in pendant position (A) at least one organic group selected from the group consisting of polyoxyalkylene-functional organic groups, alkyl groups having at least 12 carbon atoms, and polydialkylsiloxane chain-containing organic groups and also contains, in pendant position or molecular chain terminal position, (B) at least one perfluoroalkyl-functional organic group with the general formula F(CF
2
)
a
—R
1
— in which R
1
is alkylene or alkyleneoxyalkylene and a is an integer with a value of at least 3.
The polyoxyalkylene-functional organic group can be expressed by the general formula —(R
2
)
b
—O—(R
3
O)
c
—R
4
in which R
2
is a divalent hydrocarbon group; R
3
is a C
1
to C
4
divalent hydrocarbon group; R
4
is the hydrogen atom, a monovalent hydrocarbon group, or an acyl group; b is 0 or 1; and c is an integer from 1 to 300 and preferably is an integer with a value of at least 5. This polyoxyalkylene-functional organic group can be specifically exemplified by the following:
—C
3
H
6
O(C
2
H
4
O)
12
CH
3
,
—C
3
H
6
O(C
3
H
6
O)
20
CH
3
,
 —C
3
H
6
O(C
2
H
4
O)
6
(C
3
H
6
O)
20
CH
3
,
—C
3
H
6
O(C
2
H
4
O)
20
H,
—C
3
H
6
O(C
3
H
6
O)
40
H,
—C
3
H
6
O(C
2
H
4
O)
20
(C
3
H
6
O)
20
H,
—C
3
H
6
O(C
3
H
6
O)
40
COCH
3
, and
—C
3
H
6
O(C
2
H
4
O)
20
(C
3
H
6
O)
20
COCH
3
.
The alkyl having at least 12 carbons can be exemplified by n-dodecyl, n-tetradecyl, n-hexadecyl, and n-octadecyl.
The polydialkylsiloxane chain-containing organic group in pendant position can be exemplified by alkylene or alkyleneoxyalkylene to which a polydimethylsiloxane chain is bonded. The polydialkylsiloxane preferably has a degree of polymerization of at least 5. The polydialkylsiloxane chain-containing organic group can be exemplified by groups with the following general formula
in which R
1
is alkylene or alkyleneoxyalkylene, R is a substituted or unsubstituted monovalent hydrocarbon group, and d is an integer with a value from 1 to 500. This group can be specifically exemplified by groups with the following formulas in which Me is an abbreviation for the methyl group.
—C
2
H
4
{Me
2
SiO}
40
Me
2
SiC
4
H
9
—C
2
H
4
{Me
2
SiO}
50
SiMe
3
—C
3
H
6
{Me
2
SiO}
40
Me
2
SiC
4
H
9
—C
2
H
4
{Me
2
SiO}
60
SiMe
3
.
The perfluoroalkyl-functional organic group (B) has the general formula F(CF
2
)
a
—R
1
— in which R
1
is alkylene or alkyleneoxyalkylene and a is an integer with a value of at least 3, preferably a value in the range from 4 to 10. The alkylene encompassed by R
1
is preferably ethylene or propylene, while the alkyleneoxyalkylene encompassed by R
1
can be exemplified by ethyleneoxyethylene, ethyleneoxypropylene, and propyleneoxypropylene. The subject perfluoroalkyl-functional organic group can be specifically exemplified by groups with the following formulas.
—C
2
H
4
C
4
F
9
—C
2
H
4
C
6
F
13
—C
2
H
4
C
8
F
17
—C
3
H
6
C
4
F
9
—C
2
H
4
OC
2
H
4
C
8
F
17
.
The polydiorganosiloxane dispersibility improver can be exemplified by compounds with the following average formula.
R in this general formula denotes substituted or unsubstituted monovalent hydrocarbon groups and can be specifically exemplified by C
1
to C
30
alkyl, alkenyl, aryl, and arylalkyl. Methyl and phenyl are preferred for R.
B is the perfluoroalkyl-functional organic group with the general formula F(CF
2
)
a
—R
1
— in which R
1
is alkylene or alkyleneoxyalkylene and a is an integer with a value of at least 3.
D is an organic group selected from polyoxyalkylene-functional organic groups, alkyl groups having at least 12 carbon atoms, and polydialkylsiloxane chain-containing organic groups.
E is a group selected from R, B, and D.
x is a number with a value from 0 to 500, y is a number from 1 to 500, z is a number from 1 to 500, and (x+y+z) preferably falls in the range from 2 to 1500, more preferably 5 to 1,000. When one side of this diorganopolysiloxane (e.g. (E)) is the perfluoroalkyl-functional organic group (B), y may be 0.
The polydiorganosiloxane dispersibility improver is preferably a polydiorganosiloxane in which the perfluoroalkyl-functional organic group (B) and the fluorine-free substituent constituting the organic group (A) are disposed as grafted chains along a siloxane main chain.
The polydiorganosiloxane dispersibility improver can be exemplified by the following compounds.
The polydiorganosiloxane dispersibility improver can be synthesized by the addition reaction, for example, of polysiloxane with the following average compositional formula
with, for example, the alkenyl-functional polyoxyalkylene compound CH
2
═CHCH
2
O(C
2
H
4
O)
10
H, or an alkenyl-functional hydrocarbon compound such as an &agr;-olefin, or a vinyl-functional dimethylpolysiloxane such as CH
2
═CH{(CH
3
)
2
SiO}
40
(CH
3
)
2
SiR′ (R′=monovalent hydrocarbon groups), by heating in the presence of a catalyst, for example, chloroplatinic acid, and optionally in an organic solvent.
The polydiorganosiloxane dispersibility improver has a molecular weight preferably in the range from 1,000 to 1 million and particularly preferably in the range from 10,000 to 100,000. The fluorine content of this polydiorgan

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