Triazene oxide-transition metal complexes as hydrosilylation catalysts
First Claim
1. 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
whereM is Pt, Pd, Rh, Ru, Os or Ir,R1 is a monovalent, unsubstituted or substituted hydrocarbon radical having from 1 to 18 carbon atoms per radical, a radical of the formula --SiR2c (OR2)3-C or A,R2 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,R3 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, --NH2, --NR22, --NO2, --OH, OR2, --SH, --CN, --COOH, --COCl, --CONH2, --COR2, --CHO, --SO2 NHR2, --SO3 H, --SO2 Cl or --R4 --SiR2c (OR2)3-c,R4 is a divalent hydrocarbon radical having from 1 to 8 carbon atoms per radical,R2 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, NH3, P(C2 H5)3, P(C6 H5)3, H, CO, 1,5-cyclooctadiene, pyridine, bipyridine, acetate, acetylacetonate, phenylnitrile, ethylenediamine, acetonitrile, 2,5-norbornadiene, nitrate, nitrite, H2 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 andc is 0, 1, 2 or 3,wherein the triazene oxide-transition metal complexes are activated by heating at temperatures of from 50°
1)
C. to 250°
C. irradiation with light, or by heating and irradiation with light.
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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° C. to 250° C. and/or by irradiation with light.
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Citations
4 Claims
- 1. 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
- space="preserve" listing-type="equation">M(ANNNOR.sup.1).sub.a X.sub.b (
1)
where M is Pt, Pd, Rh, Ru, Os or Ir, R1 is a monovalent, unsubstituted or substituted hydrocarbon radical having from 1 to 18 carbon atoms per radical, a radical of the formula --SiR2c (OR2)3-C or A, R2 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, R3 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, --NH2, --NR22, --NO2, --OH, OR2, --SH, --CN, --COOH, --COCl, --CONH2, --COR2, --CHO, --SO2 NHR2, --SO3 H, --SO2 Cl or --R4 --SiR2c (OR2)3-c, R4 is a divalent hydrocarbon radical having from 1 to 8 carbon atoms per radical, R2 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, NH3, P(C2 H5)3, P(C6 H5)3, H, CO, 1,5-cyclooctadiene, pyridine, bipyridine, acetate, acetylacetonate, phenylnitrile, ethylenediamine, acetonitrile, 2,5-norbornadiene, nitrate, nitrite, H2 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°
C. to 250°
C. irradiation with light, or by heating and irradiation with light. - space="preserve" listing-type="equation">M(ANNNOR.sup.1).sub.a X.sub.b (
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2. 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.
- 3. A triazene oxide-platinum complex of the formula
- space="preserve" listing-type="equation">Pt (ANNNOR.sup.1).sub.a X.sub.b (VII)
where A is identical or different and is a radical of the formula ##STR6## R1 is a monovalent, unsubstituted or substituted hydrocarbon radical having from 1 to 18 carbon atoms per radical, a radical of the formula --SiR2c (OR2)3-c or A, X is identical or different and is a ligand selected from the group consisting of Cl, Br, I, NH3, P(C2 H5)3, P(C6 H5)3, H, CO, 1,5-cyclooctadiene, pyridine, bipyridine, acetate, acetylacetonate, phenylnitrile, ethylenediamine, acetonitrile, 2,5-norbornadlene, nitrate, nitrite, H2 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.
- 4. A process for preparing triazene oxide-platinum complexes of formula VII, which comprises reacting triazene hydroxides of formula
- space="preserve" listing-type="equation">ANNNOHR.sup.1 (VIII),
in the presence of bases with platinum compounds of the formula
space="preserve" listing-type="equation">ptX.sub.d (IX),where A is identical or different and is a radical of the formula ##STR7## R1 is a monovalent, unsubstituted or substituted hydrocarbon radical having from 1 to 18 carbon atoms per radical, a radical of the formula --SiR2c (OR2)3-c or A, and X is identical or different and is a ligand selected from the group consisting of Cl, Br, I, NH3, P(C2 H5)3, P(C6 H5)3, H CO, 1,5-cyclooctadiene, pyridine, bipyridine, acetate, acetylacetonate, phenylnitrile, ethylenediamine, acetonitrile, 2,5-norbornadiene, nitrate, nitrite, H2 O, benzene, diphenylphosphinoethane, 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, ethylene and diphenylacetylene and d is an integer from 1 to 6.
Specification
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- Resources
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Current AssigneeWacker-Chemie GmbH (Dr. Alexander Wacker Familiengesellschaft Mit Beschrã¤Nkter Haftung)
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Original AssigneeWacker-Chemie GmbH (Dr. Alexander Wacker Familiengesellschaft Mit Beschrã¤Nkter Haftung)
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InventorsWolferseder, Josef, Dauth, Jochen, Deubzer, Bernward
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Primary Examiner(s)Shaver, Paul F.
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Application NumberUS08/437,830Time in Patent Office300 DaysField of Search556/9, 556/12, 556/136, 556/137, 556/479, 528/15, 528/14, 546/4, 546/12, 546/14, 549/214, 549/3, 549/206, 549/212, 534/551, 534/552, 548/402, 502/152, 502/158, 502/167US Class Current556/9CPC Class CodesB01J 2231/323 Hydrometalation, e.g. bor-,...B01J 2531/821 RutheniumB01J 2531/822 RhodiumB01J 2531/824 PalladiumB01J 2531/825 OsmiumB01J 2531/827 IridiumB01J 2531/828 PlatinumB01J 31/1805 the ligands containing nitr...C07F 15/0066 without a metal-carbon linkageC07F 15/008 without a metal-carbon linkageC07F 15/0093 without a metal-carbon linkageC08G 77/08 characterised by the cataly...C08G 77/12 containing silicon bound to...C08G 77/20 containing silicon bound to...C08G 77/26 nitrogen-containing groupsC08L 2666/52 Metal-containing compoundsC08L 83/00 Compositions of macromolecu...C08L 83/04 Polysiloxanes
