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US4780554A Expired / Lapsed US ⏱️ 0.0 years remaining

O-silylated ketene acetals and enol ethers and method of preparation

Assignee: Witco Corp
•
Filing: 1985-06-06
•
Granted: 1988-10-25
•
Expires: 2005-06-06
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Abstract

Abstract Novel O-silylated ketene acetals and enol ethers are prepared via the 1,4-hydrosilation of a hydrosilation composition selected from the group consisting of aminosilanes, siloxanes and alkylalkoxysilanes with an α,β-unsaturated carbonyl in the presence of a rhodium catalyst.

Inventors

  • 👤 Jennifer M. Quirk
  • 👤 Linda K. Kozak
  • 👤 Bernard Kanner

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 23:50
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/38; C07; C07F; C07F7/00; C07F7/02; C07F7/025; C07F7/04; C07F7/08; C07F7/18; C07F7/1804; C07F7/21; C08F; C08F30/00; C08F30/04; C08F30/08

Claims Analysis

Total Claims: 41
Claim 1
Independent Claim 242 words
A O-silylated ketene acetal or enol ether selected from the group of O-silylated ketene acetals and enol ethers consisting essentially of: (a) O-aminosilylated ketene acetals and enol ethers of the general formula: ##STR7## (b) O-siloxanesilylated ketene acetals and enol ethers of the general formulae: ##STR8## (c) O-alkoxysilylated ketene acetals of the general formula: ##STR9## wherein R, R 1 , and R 2 are individually alkyl or aryl group containing 1 to 8 carbon atoms and R can be hydrogen; R 3 , R 4 , R 5 , R 6 , R 7 , and R 10 are individually alkyl groups containing 1 to 8 carbon atoms; R 8 is hydrogen or an alkyl or aryl groups having 1 to 8 carbon atoms; R 9 are individually alkyl or aryl groups having 1 to 8 carbon atoms; Z is selected from the group consisting of hydrogen, an alkyl group, an aryl group, an alkoxy group and an aryloxy group containing from one to fifteen carbon atoms and a has a value of 0 or 1, b has a value of 0 or 1, y has a value from 1 to 500, z has a value from 0 to 499, and, the sum of y+z equals from 1 to 500 with the proviso that if z is 0, a+b must equal at least one; x has a value of 1, 2 or 3; and v has a value of 0, 1 or 2.
Claim 2
Dependent Claim 242 words
A O-silylated ketene acetal or enol ether selected from the group of O-silylated ketene acetals and enol ethers consisting essentially of: (a) O-aminosilylated ketene acetals and enol ethers of the general formula: ##STR7## (b) O-siloxanesilylated ketene acetals and enol ethers of the general formulae: ##STR8## (c) O-alkoxysilylated ketene acetals of the general formula: ##STR9## wherein R, R 1 , and R 2 are individually alkyl or aryl group containing 1 to 8 carbon atoms and R can be hydrogen; R 3 , R 4 , R 5 , R 6 , R 7 , and R 10 are individually alkyl groups containing 1 to 8 carbon atoms; R 8 is hydrogen or an alkyl or aryl groups having 1 to 8 carbon atoms; R 9 are individually alkyl or aryl groups having 1 to 8 carbon atoms; Z is selected from the group consisting of hydrogen, an alkyl group, an aryl group, an alkoxy group and an aryloxy group containing from one to fifteen carbon atoms and a has a value of 0 or 1, b has a value of 0 or 1, y has a value from 1 to 500, z has a value from 0 to 499, and, the sum of y+z equals from 1 to 500 with the proviso that if z is 0, a+b must equal at least one; x has a value of 1, 2 or 3; and v has a value of 0, 1 or 2.
Claim 3
Dependent Claim 31 words
The O-silylated ketene acetal and enol ether of claim 1 wherein R, R 1 and R 2 are individually methyl ethyl or phenyl groups and x has a value of 3.
Claim 4
Dependent Claim 39 words
The O-silylated ketene acetal and enol ether of claim 1 wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 10 are methyl groups.
Claim 5
Dependent Claim 14 words
The O-silylated ketene acetal and enol ether of claim 1 wherein v is 0.
Claim 6
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-bis(trimethylsilyloxy)methylsiloxyethylene.
Claim 7
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-bis(trimethylsilyloxy)methylsiloxyethylene.
Claim 8
Dependent Claim 1 words
1-methyl-2-methoxy-2-bis(trimethylsilyloxy)methylsiloxyethylene.
Claim 9
Dependent Claim 1 words
1-methyl-2-methoxy-2-bis(trimethylsilyloxy)methylsiloxyethylene.
Claim 10
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-heptamethylcyclotetrasiloxyethylene.
Claim 11
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-heptamethylcyclotetrasiloxyethylene.
Claim 12
Dependent Claim 1 words
1,3-bis(1,1-dimethyl-2-methoxy-2-ethenoxy)-1,1,3,3-tetramethyldisiloxane.
Claim 13
Dependent Claim 1 words
1,3-bis(1,1-dimethyl-2-methoxy-2-ethenoxy)-1,1,3,3-tetramethyldisiloxane.
Claim 14
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-triisopropoxysiloxyethylene.
Claim 15
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-triisopropoxysiloxyethylene.
Claim 16
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-tritertbutoxysiloxyethylene.
Claim 17
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-tritertbutoxysiloxyethylene.
Claim 18
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-1-triethoxysiloxyethylene.
Claim 19
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-1-triethoxysiloxyethylene.
Claim 20
Dependent Claim 1 words
1-methyl-2-methoxy-2-tritertbutoxysiloxyethylene.
Claim 21
Dependent Claim 1 words
1-methyl-2-methoxy-2-tritertbutoxysiloxyethylene.
Claim 22
Dependent Claim 1 words
1-methyl-2-methoxy-2-triisopropoxysiloxyethylene.
Claim 23
Dependent Claim 1 words
1-methyl-2-methoxy-2-triisopropoxysiloxyethylene.
Claim 24
Dependent Claim 1 words
1-methyl-2-methoxy-2-tris(dimethylamino)siloxyethylene.
Claim 25
Dependent Claim 1 words
1-methyl-2-methoxy-2-tris(dimethylamino)siloxyethylene.
Claim 26
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-tris(dimethylamino)siloxyethylene.
Claim 27
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-tris(dimethylamino)siloxyethylene.
Claim 28
Dependent Claim 248 words
A process for preparing O-silylated ketene acetals and enolethers which comprises a 1,4-hydrosilation of a hydrosilation composition selected from the group consisting of: (a) aminosilanes of the formula: H--Si(NRR.sup.1)×(R.sup.2).sub.3--x ; (b) siloxanes of the formula: ##STR10## and (c) alkoxysilanes of the formula: ##STR11## with an α, β-unsaturated carbonyl compound of the formula: ##STR12## in the presence of a rhodium catalyst wherein R, R 1 , and R 2 are individually alkyl or aryl group containing 1 to 8 carbon atoms and R can be hydrogen; R 3 , R 4 , R 5 , R 6 , R 7 , and R 10 are individually alkyl groups containing 1 to 8 carbon atoms; R 8 is hydrogen or an alkyl or aryl groups having 1 to 8 carbon atoms; R 9 are individually alkyl or aryl groups having 1 to 8 carbon atoms; Z is selected from the group consisting of hydrogen, an alkyl group, an aryl group, an alkoxy group and an aryloxy group containing from one to fifteen carbon atoms and a has a value of 0 or 1, b has a value of 0 or 1, y has a value from 1 to 500, z has a value from 0 to 499, and, the sum of y+z equals from 1 to 500 with the proviso that if z is 0, a+b must equal at least one; x has a value of 1, 2 or 3; and v has a value of 0, 1 or 2.
Claim 29
Dependent Claim 248 words
A process for preparing O-silylated ketene acetals and enolethers which comprises a 1,4-hydrosilation of a hydrosilation composition selected from the group consisting of: (a) aminosilanes of the formula: H--Si(NRR.sup.1)×(R.sup.2).sub.3--x ; (b) siloxanes of the formula: ##STR10## and (c) alkoxysilanes of the formula: ##STR11## with an α, β-unsaturated carbonyl compound of the formula: ##STR12## in the presence of a rhodium catalyst wherein R, R 1 , and R 2 are individually alkyl or aryl group containing 1 to 8 carbon atoms and R can be hydrogen; R 3 , R 4 , R 5 , R 6 , R 7 , and R 10 are individually alkyl groups containing 1 to 8 carbon atoms; R 8 is hydrogen or an alkyl or aryl groups having 1 to 8 carbon atoms; R 9 are individually alkyl or aryl groups having 1 to 8 carbon atoms; Z is selected from the group consisting of hydrogen, an alkyl group, an aryl group, an alkoxy group and an aryloxy group containing from one to fifteen carbon atoms and a has a value of 0 or 1, b has a value of 0 or 1, y has a value from 1 to 500, z has a value from 0 to 499, and, the sum of y+z equals from 1 to 500 with the proviso that if z is 0, a+b must equal at least one; x has a value of 1, 2 or 3; and v has a value of 0, 1 or 2.
Claim 30
Dependent Claim 20 words
The process of claim 16 wherein the catalyst concentration is 0.00001 to 0.05 mole percent based on the hydrosilation composition.
Claim 31
Dependent Claim 16 words
The process of claim 16 wherein the hydrosilation occurs at a temperature greater than 40° C.
Claim 32
Dependent Claim 13 words
The process of claim 18 wherein the temperature is 70° to 150° C.
Claim 33
Dependent Claim 10 words
The process of claim 16 wherein a solvent is employed.
Claim 34
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-methyldiethoxysiloxyethylene.
Claim 35
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-methyldiethoxysiloxyethylene.
Claim 36
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-dimethylaminodimethylsiloxyethylene.
Claim 37
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-dimethylaminodimethylsiloxyethylene.
Claim 38
Dependent Claim 3 words
1,1-dimethyl-2-methoxy-2-methyl bis (dimethylamino)siloxyethylene.
Claim 39
Dependent Claim 3 words
1,1-dimethyl-2-methoxy-2-methyl bis (dimethylamino)siloxyethylene.
Claim 40
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-dimethylethoxysiloxyethylene.
Claim 41
Dependent Claim 1 words
1,1-dimethyl-2-methoxy-2-dimethylethoxysiloxyethylene.

References Cited (Backward Citations)

US4294975A Cited
EP0068887A1 Cited
US4417034A Cited
US4414372A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1991-10-25 1992-04-25 1992-10-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1995-10-25 1996-04-25 1996-10-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1999-10-25 2000-04-25 2000-10-25 $7700.00 Window Closed / Lapsed

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