Triazene oxide-transition metal complexes as hydrosilylation catalysts
AssigneeWacker Chemie AG
InventorsJochen Dauth, Josef Wolferseder, Bernward Deubzer
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Abstract
Organosilicon compounds having Si-bonded hydrogen atoms are reacted with organic compounds having aliphatic multiple bonds in the presence of triazene oxide-transition metal complexes. The triazene oxide-transition metal complexes are activated by heating at temperatures of from 50.degree. C. to 250.degree. C. and/or by irradiation with light.
Claims4
A process comprising reacting organosilicon compounds having Si-bonded hydrogen atoms with organic compounds having aliphatic multiple bonds in the presence of triazene oxide-transition metal complexes of the formula
- M(ANNNOR.sup.1).sub.a X.sub.b ( 1)
- where
- M is Pt, Pd, Rh, Ru, Os or Ir,
- R.sup.1 is a monovalent, unsubstituted or substituted hydrocarbon radical having from 1 to 18 carbon atoms per radical, a radical of the formula --SiR.sup.2.sub.c (OR.sup.2).sub.3-C or A,
- R.sup.2 is identical or different and is an alkyl radical having from 1 to 8 carbon atoms per radical,
- A is identical or different and is a radical of the formula ##STR5## G is CH or N Q is S, O or NH,
- R.sup.3 is a monovalent, unsubstituted or substituted hydrocarbon radical having from 1 to 12 carbon atoms per radical or is a radical of the formula --F, --Cl, --Br, --I, --H, --NH.sub.2, --NR.sup.2.sub.2, --NO.sub.2, --OH, OR.sup.2, --SH, --CN, --COOH, --COCl, --CONH.sub.2, --COR.sup.2, --CHO, --SO.sub.2 NHR.sup.2, --SO.sub.3 H, --SO.sub.2 Cl or --R.sup.4 --SiR.sup.2.sub.c (OR.sup.2).sub.3-c,
- R.sup.4 is a divalent hydrocarbon radical having from 1 to 8 carbon atoms per radical,
- R.sup.2 is identical or different and is an alkyl radical having from 1 to 8 carbon atoms per radical,
- X is identical or different and is a ligand selected from the group consisting of Cl, Br, I, NH.sub.3, P(C.sub.2 H.sub.5).sub.3, P(C.sub.6 H.sub.5).sub.3, H, CO, 1,5-cyclooctadiene, pyridine, bipyridine, acetate, acetylacetonate, phenylnitrile, ethylenediamine, acetonitrile, 2,5-norbornadiene, nitrate, nitrite, H.sub.2 O, benzene, diphenylphosphinoethane, 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, ethylene and diphenylacetylene,
- a is 1, 2, 3 or 4,
- b is 0, or an integer from 1 to 6 and
- c is 0, 1, 2 or 3,
- wherein the triazene oxide-transition metal complexes are activated by heating at temperatures of from 50.degree. C. to 250.degree. C. irradiation with light, or by heating and irradiation with light.
Crosslinkable organopolysiloxane compositions comprising
- (1) organopolysiloxanes which have radicals containing aliphatic carbon-carbon multiple bonds,
- (2) organopolysiloxanes having Si-bonded hydrogen atoms, or in place of organopolysiloxanes (1) and (2)
- (3) organopolysiloxanes which have radicals containing aliphatic carbon-carbon multiple bonds and Si-bonded hydrogen atoms, and
- (4) triazene oxide-transition metal complexes of formula (I) as catalysts.
A triazene oxide-platinum complex of the formula
- Pt (ANNNOR.sup.1).sub.a X.sub.b (VII)
- where
- A is identical or different and is a radical of the formula ##STR6## R.sup.1 is a monovalent, unsubstituted or substituted hydrocarbon radical having from 1 to 18 carbon atoms per radical, a radical of the formula --SiR.sup.2.sub.c (OR.sup.2).sub.3-c or A,
- X is identical or different and is a ligand selected from the group consisting of Cl, Br, I, NH.sub.3, P(C.sub.2 H.sub.5).sub.3, P(C.sub.6 H.sub.5).sub.3, H, CO, 1,5-cyclooctadiene, pyridine, bipyridine, acetate, acetylacetonate, phenylnitrile, ethylenediamine, acetonitrile, 2,5-norbornadlene, nitrate, nitrite, H.sub.2 O, benzene, diphenylphosphinoethane, 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, ethylene and diphenylacetylene,
- a is 1, 2, 3 or 4, and
- b is 0, or an integer from 1 to 6.
A process for preparing triazene oxide-platinum complexes of formula VII, which comprises reacting triazene hydroxides of formula
- ANNNOHR.sup.1 (VIII),
- in the presence of bases with platinum compounds of the formula
- ptX.sub.d (IX),
- where
- A is identical or different and is a radical of the formula ##STR7## R.sup.1 is a monovalent, unsubstituted or substituted hydrocarbon radical having from 1 to 18 carbon atoms per radical, a radical of the formula --SiR.sup.2.sub.c (OR.sup.2).sub.3-c or A, and
- X is identical or different and is a ligand selected from the group consisting of Cl, Br, I, NH.sub.3, P(C.sub.2 H.sub.5).sub.3, P(C.sub.6 H.sub.5).sub.3, H CO, 1,5-cyclooctadiene, pyridine, bipyridine, acetate, acetylacetonate, phenylnitrile, ethylenediamine, acetonitrile, 2,5-norbornadiene, nitrate, nitrite, H.sub.2 O, benzene, diphenylphosphinoethane, 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, ethylene and diphenylacetylene and d is an integer from 1 to 6.
Dependencies are inferred from the claim text.