Multi-reactive silicon compound having polyalkyleneglycol...

Details Multi-reactive silicon compound having polyalkyleneglycol... Multi-reactive silicon compound having polyalkyleneglycol...

2001-06-13

2003-04-29

Moore, Margaret G. (Department: 1712)

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

Synthetic resins

From silicon reactant having at least one...

C528S029000, C528S031000, C556S435000

Reexamination Certificate

active

06555644

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a multi-reactive polyalkyleneglycol ether having polyalkyleneglycol substituents and a synthetic method thereof, and more particularly, to a coupling agent having not only multiple halogen substituents to provide high reactivity with living polymeric anions but also polyalkyleneglycol substituents to enhance compatibility with inorganic fillers, and a synthetic method thereof.
BACKGROUND OF THE INVENTION
Elastomers are easily synthesized and have interesting mechanical properties, including elasticity, and broadly used in various applications such as tires, automobile parts, shock absorbents, shoes and packing. Such elastomers have been developed for organic-inorganic hybrid materials, which are synthesized by mixing silica or glass fibers in vulcanization in order to improve thermal stabilities and mechanical strength.
However, organic polymers are generally incompatible with inorganic fillers in the preparation of such organic-inorganic hybrid materials. To solve this problem, coupling agents have been introduced, or the organic polymers are chemically modified to improve the compatibility with inorganic materials. For the second solution, as well known in the related art, the living polymer is reacted with anion reactive terminators to produce a polymer having inorganophile substituents.
Miura et al., for example, reported a method for preparing a polymer modified with 4-formylphenylalkoxyamine in the anionic polymerization of butadiene (Macromolecules, 1999, 32(25), 8356).
Bronstert et al. disclosed a method for preparing a polymer modified with hydroxyethylamino or hydroxyethylpolyoxyethyleneamino compound (Germany Ger. Offen., 5 pp.).
However, the compounds used in the above documents have still problems of insufficient compatibility with inorganic particles such as silica. In an attempt to solve this problem, many studies have been reported on an organic-inorganic hybrid polymer using silicon compounds. For example, Korean Patent No. 95-704405 discloses a method for bonding hexamethylchlorosiloxane to the end of a living polymer. While the problem related to the phase separation between inorganic fillers and organic polymer is somewhat solved in this method, it is difficult to increase the molecular weight of the polymer and enhance the mechanical properties of the polymer. In order to increase the molecular weight of the polymer and thus improve the mechanical properties of end modified polymers, multi-functional silicon containing terminators are demanded.
On the other hand, silicon containing compounds having halogen as terminal or branched substituents are used as additives in coating, coupling agent, adhesive and silant in order to enhance mechanical properties of the coating surface or the substrate as well as to improve thermal stability and compatibility.
For example, U.S. Pat. No. 5,858,468 discloses a composition comprising a mixture of (a) a polysiloxane having unsaturated groups and (b) a polysiloxane containing reactive Si—H groups. This composition is useful for preparing a coating composition curable at ambient temperature.
U.S. Pat. No. 5,373,079 discloses a polydimethylsiloxane having alkoxy, acyloxy, N-methylbenzamido or alkyl groups. Also, U.S. Pat. No. 5,340,899 discloses a sealant composition comprising a mixture of (a) a polysiloxane having hydroxy end groups and (b) a polysiloxane having vinyl or methylacetamido end groups. This composition is useful for reducing the modulus of the siloxane sealant.
U.S. Pat. No. 5,194,553 discloses a method for preparing an organofunctional-terminated polydiorganosiloxane polymer and a copolymer thereof, which method is useful for making a polydimethyl siloxane having 5-hexenyl end groups. This patent also discloses a method for preparing an organofunctional-terminated polydiorganosiloxane polymer using an organofunctional chlorosilane end-blocker, and a method for preparing an organofunctional-terminated polydiorganosiloxane copolymer using an organofunctional chlorosilane end-blocker and an organofunctional chlorosilane.
These reactive silicon compounds are capable of reacting with at least two living polymers to produce multi-substituted elastomer when they have the functional groups with at least two substituents. However, the polydimethylsiloxane is ready to be decomposed prior to reaction with the living polymer due to its low storage stability and very poor in reactivity with living polymeric anions, which makes it difficult to activate multi-substitution reactions.
Thus there is a need of providing a silicon compound having high storage stability and excellent reactivity.
U.S. Pat. No. 6,005,036 discloses a method for preparing a polysilane compound used as a process stabilizer. Also, the halogen-substituted silicon compounds are widely used in various applications such as adhesion additives (U.S. Pat. No. 6,060,559); water-absorbent agents (U.S. Pat. No. 5,981,070); and coatings. Thus there is a need of providing such a silicon compound containing functional groups such as halogen as well as polar functional groups.
SUMMARY OF THE INVENTION
In an attempt to solve the problems, the inventors of this invention have studied on a synthesis of silicon containing terminators, particularly, silicon compound having polar substituents with excellent compatibility with inorganic fillers, and contrived halosilyl polyalkyleneglycol ether macromers having at least one polyalkyleneglycol substituent.
It is, therefore, an object of the present invention to provide halosilyl polyalkyleneglycol ether macromers having polar functional groups and at least two halogen substituents that can participate in various substitution reactions, more specifically, halosilyl polyalkyleneglycol ether macromers reactive to at least one equivalent of polymers in an anionic or cationic polymerization reaction.
To achieve the above object of the present invention, there is provided a reactive halosilyl polyalkyleneglycol ether containing at least two functional groups with at least one polyalkyleneglycol substituent and at least two halogen substituents, the reactive halosilyl polyalkyleneglycol ether having a number average molecular weight of 200 to 10,000 and being represented by the formula 1, (X)
a
(R)
b
(R
1
)
c
Si—C(R
4
)(R
5
)—Si(X)
d
(R)
e
(R
2
)
f
, in which X is a halogen atom selected from the group consisting ofF, Cl, Br and I; R
1
and R
2
are the same or different and independently represent hydrogen, an alkyl group containing 1 to 10 carbon atoms or a C
1
to C
10
alkyl group having F or Cl substituents; R
4
and R
5
are the same or different and independently represent hydrogen, Si(X)
a
(R)
b
(R
1
)
c
or Si(X)
d
(R)
e
(R
2
)
f
; R is a polyalkyleneglycol group represented by the formula {C(R
6
)(R
7
)CH(R
8
)C(R
6
)(R
7
)Z}—{C(R
6
)(R
7
)C(R
6
)(R
7
)O}
g
R
9
; R
6
, R
7
and R
8
are the same or different and independently represent hydrogen, an alkyl group containing 1 to 10 carbon atoms, or a C
1
to C
10
alkyl group having F or Cl substituents; R
9
is methyl or ethyl; Z is oxygen or p-substituted benzene ring (C
6
H
4
); a and d are the same or different and independently represent a number from 1 to 3; b and e are the same or different and independently represent a number from 0 to 2; c and fare the same or different and independently represent a number 0 or 1, wherein a+b+c+d+e+f=6; and g is a number from 1 to 20.
The reactive halosilyl polyalkyleneglycol ether represented by the formula 1 is synthesized by reacting a halogen-substituted silane compound having a Si—H bond as represented by the formula 2, (X)
a
(H)
b
(R
1
)
c
Si—C(R
4
)(R
5
)—Si(X)
d
(H)
e
(R
2
)
f
with a polyalkyleneglycol ether having a double bond as represented by the formula 3, {C(R
6
)(R
7
)═C(R
8
)C(R
6
)(R
7
)Z}—{C(R
6
)(R
7
)C(R
6
)(R
7
)O}
g
R
9
, in which X, Z, R
1
to R
9
and a to g are as defined above formula 1, in the presence of a hydrosilylation catalyst.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMEN

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