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US 7,402,689 B2Granted
Vinylchloroformate-free synthesis of vinyl and allyl(thio) carbamates
AssigneeBausch & Lomb Incorporated
InventorsDavid E. Seelye, Jay F. Kunzler, Joseph C. Salamone
Life of this patent
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Abstract
The invention generally relates to methods of forming vinyl(thio)carbamates and more particularly to a vinylchloroformate-free method of synthesizing (N-vinyloxycarbonyl)-3-aminopropyltris(trimethylsiloxysilane).
Claims24
A method for making a compound represented by the following formula (I):
- (CH2═CH(CH2)bYC(O)N)xR1 (I)
- wherein x is 0 or 1, b is 0 or 1, Y is O or S and R1 is a mono- or di-functional organic siloxy containing radical, the method comprising:
- reacting a compound represented by formula (II):
- CH2═CH(CH2)bOSi(CH3)3 (II)
- wherein b is 0 or 1,
- with a compound represented by formula (III):
- (Y═C═N—(CH2)m)x—R1 (III):
- wherein x is 0 or 1, Y is O or S, m is 0 to 20 and R1 is a mono- or di-functional organic siloxy containing radical to provide the compound of formula (I).
5 more elements
A method of synthesizing vinyl carbamates comprising:
- providing a mixture of isocyanopropyl tris(trimethylsiloxy), trimethyl(vinyloxy)silane, water and catalyst;
- dissolving the mixture in an organic solvent to yield a reaction mixture;
- and
- subjecting the reaction mixture to reaction conditions suitable to yield a vinylcarbamate product.
1 more element
A method of making an allylcarbamate, the method comprising:
- reacting N-hexylisocyanate with a compound selected from the group consisting of trimethyl(vinyloxy)silane, allyloxytrimethylsilane, 2-(trimethylsiloxy)ethyl methacrylate, 2-(trimethylsiloxy)-1,3-cyclohexadiene and trimethyl-N-propoxysilane to yield an allylcarbamate compound.
A method of making an allyl thio carbamate, the method comprising:
- reacting N-hexylisothiocyanate with a compound selected from the group consisting of trimethyl(vinyloxy)silane, allyloxytrimethylsilane, 2-(trimethylsiloxy)ethyl methacrylate, 2-(trimethylsiloxy)-1,3-cyclohexadiene and trimethyl-N-propoxysilane to yield an allylthiocarbamate compound.
A method of synthesizing vinyl carbamates comprising:
- providing a mixture of isocyanopropyl tris(trimethylsiloxy), trimethyl(vinyloxy)silane, water and palladium (II) acetate catalyst;
- combining the mixture with dimethylacetamide to yield a reaction mixture;
- and
- subjecting the reaction mixture to reaction conditions suitable to yield a vinylcarbamate product.
1 more element
Dependencies are inferred from the claim text.