Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Patent
1997-05-16
1998-09-15
Shaver, Paul F.
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C07F 708
Patent
active
058081275
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to a hydrosilylation method and a process for the production of an organic curing agent containing hydrosilyl groups.
BACKGROUND ART
Hydrosilylation reaction in which hydrosilyl group is added to olefin is broadly known as a method for the production of organic silicon compounds and used in various applications. As an example of such applications, various hydrosilyl group-containing organic curing agents have been developed as curable liquid compositions having excellent deep curability, in order to produce rubber-like substances through cross-linking and curing of polymers by hydrosilylation reaction.
Illustratively, an agent, in which a polyorganosiloxane having 2 or more in average of vinyl groups on terminals or in molecular chain of one molecule is cross-linked with a polyorganohydrogensiloxane having, in 1 molecule, 2 or more hydrogen atoms binding to the silicon atom, has been developed and used as sealing materials and potting materials making use of its excellent weather resistance, water resistance and heat resistance.
In addition, as disclosed in JP-A-3-95266 (the term "JP-A" as used herein refers to a "published unexamined Japanese patent application"), an organic curing agent has recently been developed which contains at least 2 hydrosilyl groups (not a polymer) in its molecule instead of the polyorganohydrogensiloxane usually used in curing reaction by hydrosilylation. According to the disclosure, this organic curing agent generally has good compatibility with alkenyl group-containing organic polymers.
In consequence, it has been found that, when the aforementioned alkenyl group-containing organic polymer is cured with the aforementioned organic curing agent which contains at least 2 hydrosilyl groups in its molecule using a hydrosilylation catalyst, excellent characteristics can be obtained as follows;
(1) since the aforementioned curable composition is a homogeneous system, quickly curable and excellent in deep curability, a cured product having excellent mechanical characteristics such as sufficient tensile characteristics and the like can be obtained from the curable composition,
(2) since alkenyl group-containing organic polymers having any type of backbone skeleton can be used, curing agents applicable to markedly broad range of use can be produced, and
(3) since the aforementioned organic curing agent which is not a polymer generally has low viscosity, it is advantageous from the viewpoint of workability for the production of cured products.
Hydrosilylation reaction is used also in the production of such an organic curing agent.
In general, when the hydrosilylation reaction is carried out to effect addition of hydrosilyl groups to olefin, various transition metal complexes such as of cobalt, rhodium, nickel, palladium, platinum and the like are used as catalysts. In that case, it is necessary to exclude catalyst poisons from the reaction system as many as possible. For example, Nielsen discloses various interfering substances and inhibiting substances in U.S. Pat. No. 3,383,356, and Ashby discloses a hydrosilylation catalyst which shows a higher activity than those of conventional catalysts due to the absence of interfering impurities in JP-A-60-54734.
On the other hand, various compounds are known as storage stability imparting agents for curable compositions of hydrosilylation cross-linking system. Examples of such compounds include an ethylenic or aromatic unsaturated amide (U.S. Pat. No. 4,337,332), an acethylenic compound (U.S. Pat. No. 3,445,420), an ethylenic unsaturated isocyanate (U.S. Pat. No. 3,882,083), an olefinic siloxane (U.S. Pat. No. 3,989,667), conjugate ene-ynes (U.S. Pat. No. 4,465,818), an unsaturated hydrocarbon diester inhibitor (U.S. Pat. No. 4,256,870), a bis-hydrocarbonoxyalkyl maleate inhibitor (U.S. Pat. No. 42562096) and the like. These storage stability imparting agents, however, are aimed at inhibiting catalytic activities at around room temperature but not reducing catalytic activities at the time of heating.
Si
REFERENCES:
patent: 5621129 (1997-04-01), Hayashi et al.
Kusakabe Masato
Nakagawa Yoshiki
Kanegafuchi Kagaku Kogyo & Kabushiki Kaisha
Shaver Paul F.
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