Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From silicon reactant having at least one...
Patent
1996-05-30
1998-06-16
Marquis, Melvyn I.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From silicon reactant having at least one...
528 18, 556469, 556466, 556489, C08G 7708
Patent
active
057672172
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a process for the preparation of polyorganosiloxanes containing unsaturated functions, by dehydrogenative condensation of polyorganohydrogenosiloxanes and ethylenically and/or acetylenically unsaturated hydrocarbon compounds, in the presence of group IVA metal complexes (IUPAC).
According to the invention, this is a process for the preparation of polyorganosiloxanes containing unsaturated functions, characterized in that a polyorganohydrogenosiloxane (A) containing at least 0.1 mol %, preferably from about 1 mol % to 20 mol %, of hydrogen atoms linked directly to the silicon ("SiH") is reacted with at least a stoichiometric amount of a hydrocarbon compound (B) having at least one ethylenic or acetylenic unsaturation, in the presence of a catalytically effective amount of a dehydrogenative condensation catalyst consisting of a complex of a group IV metal of formula (I) of the metal M, the said ligand donating from 3 to 8 .pi.-electrons to the valence shell of the said metal; organosilicon ligand of the metal M, the said ligand being a .sigma.-electron donor; with the metal M, a covalent bond; of electrons in the valence shell of the complexed metal M is less than or equal to 18 and preferably greater than or equal to 8.
Among the group IV metal complexes of formula (I) which may be used as dehydrogenative condensation catalyst, mention may be made of the titanium, zirconium or hafnium complexes.
Among the ligands L which may be mentioned are the .eta..sup.3 -allyl, .eta..sup.5 -cyclopentadienyl and .eta..sup.7 -cycloheptatrienyl which may or may not be substituted, .eta..sup.6 aromatics such as substituted or unsubstituted .eta..sup.6 benzene, and the like.
Among the ligands R which may be mentioned are C.sub.1 -C.sub.8 alkyl groups, C.sub.6 -C.sub.12 aryl groups, and the like.
Among the ligands Y which may be mentioned are hydrogen atoms, halogen atoms (chlorine, fluorine, bromine and iodine), C.sub.1 -C.sub.4 alkoxy groups, and the like.
As examples of complexes, mention may be made of
The said polyorganohydrogenosiloxane (A) used may be linear, cyclic or three-dimensional. It contains units, which are the same or different, of formula (II) -C.sub.18 alkyl group, a vinyl group or a C.sub.6 -C.sub.12 aryl or aralkyl group, optionally substituted with halogen atoms (fluorine in particular), preferably at least 60 mol % of the said radicals R' representing a methyl group; units of formula (II) in which b is other than 0 being such that the said polyorganohydrogenosiloxane (A) contains at least 0.1 mol %, preferably about 1 mol % to 20 mol %, of hydrogen atoms linked directly to the silicon ("SiH").
This polyorganohydrogenosiloxane is preferably liquid; its dynamic viscosity at 25.degree. C. may be up to 1,000,000 mPa s; this viscosity is generally from about 1 to 10,000 mPa s.
The dynamic viscosity at 25.degree. C. of the silicone polymers may be measured using a Brookfield viscometer according to the AFNOR standard NFT 76 102 of February 1992.
Among the unsaturated hydrocarbon compounds (B) which may be used, mention may be made of linear or branched C.sub.2 -C.sub.24 alkenes, C.sub.6 -C.sub.12 cycloalkenes, linear or branched C.sub.2 -C.sub.24 alkynes, optionally substituted with one or more halogen atoms and/or with one or more C.sub.6 -C.sub.12 aryl groups, saturated esters of ethylenically unsaturated carboxylic acids, unsaturated esters of saturated carboxylic acids, organosilanes or organosiloxanes bearing ethylenic or acetylenic unsaturated groups, and the like.
By way of example, mention may be made of: ethylene, 1-octene, 1,4-butadiene, 1,5-hexadiene, 1,9-decadiene, perfluoro olefins of formula CF.sub.3 --(CF.sub.2).sub.0-5 --(CH.sub.2).sub.0-6 --CH.dbd.CH.sub.2, 1,5-cyclooctadiene, acetylene, 1-hexyne, styrene, ethyl acrylate, vinyltrimethylsilane, 1,3-divinyltetramethyldisiloxane, cyclopentadiene and the dimer, and the like.
In the definition of a mole of polyorganohydrogenosiloxane (A), a hydrogen atom linked directly to the silicon ("SiH") will be considered as
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Choukroun Robert
Frances Jean-Marc
Soleil Frederique
Marquis Melvyn I.
Rhone-Poulenc Chimie
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