Organosilicon compounds

Details Organosilicon compounds Organosilicon compounds

2001-04-25

2003-02-18

Moore, Margaret G. (Department: 1712)

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

Organic compounds

Silicon containing

C556S431000, C528S031000, C528S035000

Reexamination Certificate

active

06521774

ABSTRACT:

This invention relates to novel organosilicon compounds which are useful as an addition reaction crosslinking agent.
BACKGROUND OF THE INVENTION
Rubber compositions of the addition reaction curing type generally contain base polymers having alkenyl groups such as vinyl groups, compounds having hydrogen atoms directly attached to silicon atoms (i.e., SiH groups), and addition reaction catalysts such as platinum group catalysts. Curing takes place through the mechanism that the SiH groups add to alkenyl groups on the base polymer.
Many organosilicon compounds having SiH groups are known. One typical compound described in JP-A 3-197484 has the structure in which a SiH group is bonded through an oxygen atom to a silicon atom having a fluoroalkyl substituent as shown below.
This compound is capable of hydrosilylation reaction with another compound having a vinyl group and useful as a starting material from which various derivatives are synthesized. Using this compound, for instance, modifiers, resin or rubber crosslinking agents, surfactants and additives can be synthesized.
However, since this compound has an Si—O—Si linkage of the siloxane type in its molecule, this compound suffers from the likelihood of cleavage of the siloxane bond under such rigorous conditions as exposure to elevated temperature in the presence of acids or basic materials.
SUMMARY OF THE INVENTION
An object of the invention is to provide a novel SiH group-bearing organosilicon compound capable of hydrosilylation reaction with another compound having a vinyl group to form a hydrosilylated derivative which is less prone to decomposition under acidic or basic conditions.
The inventors have found that an organosilicon compound obtained by introducing an alkylene group or analogue instead of the oxygen atom in an Si—O—Si linkage is capable of hydrosilylation reaction with another compound having a vinyl group to form a hydrosilylated derivative which is less prone to decomposition under acidic or basic conditions.
The invention provides an organosilicon compound of the following general formula (1).
Herein “a” and “b” each are 0 or 1, “a” and “b” are not 0 at the same time. Z is hydrogen, —R, —M or —Q—Rf when either one of “a” and “b” is 0, and Z is —Q—, —Rf′— or —Q—Rf′—Q— when both “a” and “b” are 1. R is a monovalent hydrocarbon group of 1 to 6 carbon atoms and may be the same or different. M is a group of the following formula (2):
wherein m is an integer of 1 to 4 and R is as defined above. Q is a divalent hydrocarbon group of 1 to 15 carbon atoms which may contain an ether bond. Rf is a monovalent perfluoroalkyl or perfluorooxyalkyl group. Rf′ is a divalent perfluoroalkylene or perfluorooxyalkylene group. The letter s is 1, 2 or 3, and t is 0, 1, 2 or 3.


REFERENCES:
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patent: 3328448 (1967-06-01), Barnes et al.
patent: 3496206 (1970-02-01), Berger
patent: 5260468 (1993-11-01), Yamamoto et al.
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patent: 6087521 (2000-07-01), Jung et al.
patent: 6278011 (2001-08-01), Chen et al.
patent: A3197484 (1991-08-01), None
CRC Handbook of Chemistry and Physics, 1984, p. C-515.

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