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...
Reexamination Certificate
1999-06-22
2001-04-03
Moore, Margaret G. (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...
C528S029000, C528S038000, C106S287110, C008SDIG001, C556S445000
Reexamination Certificate
active
06211284
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to highly storage-stable organopolysiloxane compositions. More particularly, this invention relates to a highly storage-stable organopolysiloxane composition that exhibits surface-modifying activities, e.g., antistatic and anticlouding activities, and that can retain these activities long-term.
BACKGROUND OF THE INVENTION
Polyoxyalkylene-functional diorganopolysiloxanes have the ability to impart an excellent smoothness and excellent antistaticity to fiber surfaces, and for this reason are useful as fiber treatment agents (see, for example, U.S. Pat. No. 5,036,123 and Japanese Patent Publications Kokai No's. 52-91994, and 54-142400).
When dissolved or homogeneously dispersed in water, polyoxyalkylene-functional diorganopolysiloxanes cause a substantial decline in the surface tension of the solution. Therefore, polyoxyalkylene-functional diorganopolysiloxanes have also been proposed for use as spreaders for insect repellents, insecticides, and agrochemicals and as penetration assistants for fiber treatment agents (see U.S. Pat. Nos. 4,933,002 and 4,921,622, Japanese Patent Publication (PCT) No. 2-504644, and Japanese Patent Publication Kokai No's. 2-73002, 5-905).
However, when this type of polyoxyalkylene-functional diorganopolysiloxane is dissolved or homogeneously dispersed in water, the polyoxyalkylene group degrades with the passage of time. This timewise degradation results in such problems as a decline in antistatic activity or an increase in the surface tension of the solution and in extreme cases in solution turbidity and/or the production of precipitate.
A polyoxyalkylene-functional diorganopolysiloxane that also carries amino-functional organic groups has been proposed for use as a fiber treatment agent and a hair-control agent (see Japanese Patent Publication Kokai Numbers Sho 57-133279 and 59-179885 and U.S. Pat. Nos. 4,399,247, 4,459,382, and 4,450,152). A drawback to the use of this type of diorganopolysiloxane has been the manifestation of inadequate activities such as anticlouding and antistatic activities.
The object of this invention is to provide a highly storage-stable organopolysiloxane composition that is capable of the long-term retention of its surface-modifying activities, e.g., antistatic and anticlouding activities. It is a further object of this invention to provide the admixture of a special diorganopolysiloxane into a polyoxyalkylene-functional diorganopolysiloxane, wherein the special diorganopolysiloxane induces long-term retention of the surface-modifying activities that such polyoxyalkylene-functional diorganopolysiloxane imparts, such as antistatic and anticlouding activities.
SUMMARY OF THE INVENTION
This invention relates to a highly storage-stable organopolysiloxane composition comprising:
(A) a polyoxyalkylene-functional diorganopolysiloxane that is free of amino, carboxyl, and epoxy groups,
(B) a polyoxyalkylene-functional diorganopolysiloxane containing an amino-functional organic group, and
(C) water.
DETAILED DESCRIPTION OF THE INVENTION
The diorganopolysiloxane (A) used in the present invention is a siloxane that contains at least 1 polyoxyalkylene group per molecule but which is free of amino, carboxyl, and epoxy groups. Diorganopolysiloxane (A) is exemplified by a polymer with the following general formula:
Each R is independently selected from monovalent organic groups excluding amino-functional organic groups, carboxyl-functional organic groups, and epoxy-functional organic groups. R is specifically exemplified by saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, and dodecyl; unsaturated aliphatic hydrocarbon groups such as vinyl, allyl, and hexenyl; saturated alicyclic hydrocarbon groups such as cyclopentyl and cyclohexyl; aromatic hydrocarbon groups such as phenyl, tolyl, and naphthyl; halogen-substituted hydrocarbon groups; and methacrylic-functional organic groups. Substituted and unsubstituted monovalent hydrocarbon groups are preferred, and R will most typically be the methyl group.
G represents the polyoxyalkylene group —(R
1
)
a
—O—(R
2
)
b
—R
3
. R
1
represents divalent hydrocarbon groups and is exemplified by alkylene groups such as methylene, ethylene, propylene, and butylene; arylene groups such as —C
6
H
4
—; and alkylenearylene groups such as —(CH
2
)
2
C
6
H
4
—. R
2
represents C
2
to C
4
oxyalkylene groups and will generally be a —C
2
H
4
O— and/or —C
3
H
6
O— group. R
2
may be a single oxyalkylene group or may encompass two or more oxyalkylene groups. When two or more oxyalkylene groups are bonded in R
2
, their bonding configuration may be that of a random copolymer or a block copolymer. R
3
represents the hydrogen atom, monovalent hydrocarbon groups, acyl groups, and the carbamyl group. The monovalent hydrocarbon groups for R
3
are exemplified by methyl, ethyl, and propyl. The subscript a is 0 or 1, while b is a number from 1 to 100 and preferably from 5 to 50.
The groups A are selected from R and G, x is a number from 0 to 1,000 and y is a number from 0 to 100. The diorganopolysiloxane (A) is preferably soluble by itself in water or homogeneously dispersible by itself in water.
The diorganopolysiloxane (A) described above is exemplified by the following compounds:
The diorganopolysiloxane (A) can be synthesized by known methods. For example, a polyoxyalkylene-functional diorganopolysiloxane with the formula:
can be synthesized by reacting an SiH containing diorganopolysiloxane with the formula (CH
3
)
3
SiO((CH
3
)
2
SiO)
n
((CH
3
)HSiO)
m
Si(CH
3
)
3
, wherein n and m are integers, with the polyoxyethylene allyl ether CH
2
═CHCH
2
O(C
2
H
4
O)
z
H, wherein z is an integer, in the presence of 10 to 20 ppm platinum catalyst.
Each molecule of diorganopolysiloxane (B) must contain at least 1 amino-functional organic group and at least 1 polyoxyalkylene group. This diorganopolysiloxane is exemplified by compounds with the following general formula:
wherein R and G are the same as defined above, while B represents amino-functional organic groups, for example, groups with the formula —R
1
—(NHR
1
)
c
NR
4
2
and
R
1
in the preceding formula is defined as above, while R
4
is the hydrogen atom or a monovalent hydrocarbon group. The monovalent hydrocarbon groups of R
4
can be specifically exemplified by saturated aliphatic hydrocarbon groups such as methyl, ethyl, and propyl and by alicyclic hydrocarbon groups such as cyclopentyl and cyclohexyl. The two groups R
4
may be the same or different. The subscript c is 0 or 1. D is selected from R, G, B, the hydroxyl group, and alkoxy groups. The alkoxy groups are exemplified by methoxy, ethoxy, and propoxy, but will generally be methoxy or ethoxy. The subscript p has a value from 0 to 1,000, while q and r are both numbers with values from 0 to 100. The diorganopolysiloxane (B) is preferably soluble by itself in water or homogeneously dispersible by itself in water.
The diorganopolysiloxane (B) is exemplified by the following compounds:
The diorganopolysiloxane (B) can be synthesized by known methods, for example, by base-catalyzed equilibration between a polyoxyalkylene-functional diorganopolysiloxane and a diorganopolysiloxane carrying amino-functional organic groups, or by condensation among a silanol-endblocked diorganopolysiloxane, a polyoxyalkylene-functional alkoxysilane, and an alkoxysilane bearing an amino-functional organic group.
The organopolysiloxane composition of this invention comprises the solution or homogeneous dispersion of diorganopolysiloxane (A) and diorganopolysiloxane (B) in freely selected proportions in water (C). In a preferred embodiment, the blending proportions of the respective components provide an average equivalent weight for the amino-functional organic group (average amino equivalent weight) in (component (A) +component (B)) in the range from 5,000 to 500,000 and more preferably in the range from 10,000 to 100,000. The composition can be prepared, for example, by preliminarily preparing a mixtu
Ishikawa Hiroki
Naganawa Tsutomu
Ona Isao
Ozaki Masaru
Dow Corning Toray Silicone Co.
Moore Margaret G.
Richard Charles R.
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