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US 6,388,117 B2Granted
Process for preparing carbamatoorganosilanes and isocyanatoorganosilanes
AssigneeDegussa AG
InventorKlaus Pinske
Life of this patent
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Abstract
Processes for preparing carbamatoorganosilanes from aminoorganosilanes, ureas and alcohols. These compounds are useful for surface modification of inorganic and organic materials, as adhesion promoters between inorganic materials and organic polymers, as crosslinking agents for the moisture-curing of polymers, for PU sealants, in the coating and adhesive sector, and for the production of biologically active products, such as insecticides and herbicides.
Claims21
A process for preparing a carbamatoorganosilane represented by formula (V):
- R5O—(C═O)—NH—R1—Si(R2,R3,R4) (V)
- wherein R1 is an alkylene, branched alkylene, cycloalkylene, alkenylene, alkylalkoxyalkylene, arylene, alkarylene or aralkylene group;
- R2, R3, R4 are each, independently, an alkyl, branched alkyl, cycloalkyl, alkoxy, alkoxy-substituted alkoxy, siloxy, aryl alkaryl, or aralkyl group;
- R5 is an alkyl, branched alkyl, cycloalkyl, aryl, alkaryl, or aralkyl group;
- wherein R1, R2, R3 and R4 may each be, independently, substituted with one or more functional groups, comprising:
- (a) reacting an aminoorganosilane represented by formula (I), a urea represented by formula (II) and an alcohol represented by formula (IV) in a stirred-tank cascade at 150-250° C. and 7-40 bar;
- or
- (b) reacting an aminoorganosilane represented by formula (I), a urea represented by formula (II) in an alcohol solvent represented by formula (IV) in a distillation reactor at 100-130° C. and 0.7-1.5 bar (absolute) to form an ureoorganosilane represented by formula (III), followed by (ii) reacting the ureoorganosilane represented by formula (III) with an alcohol represented by formula (IV) in a pressure distillation reactor at 150-250° C. and 7-40 bar,
- H2N—R1—Si(R2,R3,R4) (I)
- H2N—(C═O)—NH2 (II)
- H2N—(C═O)—NH—R1—Si(R2,R3,R4) (III)
- R5—OH (IV)
- wherein R1, R2, R3, R4 and R5 are as defined above.
10 more elements
A process for preparing an ureoorganosilane represented by formula (III):
- H2N—(C═O)—NH—R1—Si(R2,R3,R4) (III)
- wherein R1 is an alkylene, branched alkylene, cycloalkylene, alkenylene, alkylalkoxyalkylene, arylene, alkarylene or aralkylene group;
- R2, R3, R4 are each, independently, an alkyl, branched alkyl, cycloalkyl, alkoxy, alkoxy-substituted alkoxy, siloxy, aryl alkaryl, or aralkyl group;
- wherein R1, R2, R3 and R4 may each be, independently, substituted with one or more functional groups, comprising:
- (a) reacting an aminoorganosilane represented by formula (I), a urea represented by formula (II) and an alcohol solvent represented by formula (IV) in a distillation reactor at 100-130° C. and 0.7-1.5 bar (absolute),
- H2N—R1—Si(2,R3,R4) (I)
- H2N—(C═O)—NH2 (II)
- R5—OH (IV)
- wherein R1, R,2, R3, and R4 are as defined above;
- and
- R5 is an alkyl, branched alkyl, cycloalkyl, aryl, alkaryl, or aralkyl group.
8 more elements
A process for preparing a isocyanatoorganosilane represented by formula (VI):
- OCN—R1—Si(R1,R2,R3,R4) (VI)
- wherein R1 is an alkylene, branched alkylene, cycloalkylene, alkenylene, alkylalkoxyalkylene, arylene, alkarylene or aralkylene group;
- R2, R3, R4 are each, independently, an alkyl, branched alkyl, cycloalkyl, alkoxy, alkoxy-substituted alkoxy, siloxy, aryl alkaryl, or aralkyl group;
- wherein R1, R2, R3 and R4 may each be, independently, substituted with one or more functional groups, comprising:
- (a) reacting an aminoorganosilane represented by formula (I), a urea represented by formula (II) and an alcohol represented by formula (IV) in a stirred-tank cascade at 150-250° C. and 7-40 bar;
- or
- (b) reacting an aminoorganosilane represented by formula (I), a urea represented by formula (II) in an alcohol solvent represented by formula (IV) in a distillation reactor at 100-130° C. and 0.7-1.5 bar (absolute) to form an ureoorganosilane represented by formula (III), followed by (ii) reacting the ureoorganosilane represented by formula (II) with an alcohol represented by formula (IV) in a pressure distillation reactor at 150-250° C. and 7-40 bar to produce a carbamatoorganosilane represented by formula (V);
- R5O—(C═O)—NH—R1—Si(R2,R3,R4) (V), and
- (c) catalytically cleaving the carbamatoorganosilane represented by formula (V) in the liquid phase,
- H2N—R1—Si(R2,R3,R4) (I)
- H2N—(C═O)—NH2 (II)
- H2N—(C═O)—NH—R1—Si(R2,R3,R4) (III)
- R1—OH (IV)
- wherein R1, R2, R3, and R4 are as defined above;
- and
- R5 is an alkyl, branched alkyl, cycloalkyl, aryl, alkaryl, or aralkyl group.
13 more elements
Dependencies are inferred from the claim text.