Preparation of isocyanato silanes
AssigneeMomentive Performance Materials Inc.
InventorsTiberiu L. Simandan, Roland Wagner, Holger J. Glatzer, Karl-Heinz Sockel, Karl-Heinz Stachulla, Christian Wenske
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Abstract
A process for the preparation of alkoxysilyl group-containing isocyanate compounds which includes the step of reacting carbonyl chloride ClC(═O)Cl with an alkoxysilyl group-containing amine in the presence of a high boiling point base, and optionally in the presence of an inert organic solvent, in order to minimize by product production and to simplify product purification, is disclosed.
Claims19
A process for the preparation of an alkoxysilyl group-containing isocyanate compound having the general Formula (I):
- (R1O)3-aR2aSi—R3—NCO (I)
- wherein
- each R1 is independently a branched or straight chain alkyl or cycloalkyl group of from 1 to 6 carbon atoms;
- each R2 is independently a branched or straight chain alkyl or cycloalkyl group of from 1 to 6 carbon atoms;
- R3 is a branched or straight chain alkylene or cycloalkylene group of from 1 to 12 carbon atoms, an arylene group of from 6 to 10 carbon atoms, or an aralkylene group of from 7 to 10 carbon atoms;
- and
- a is 0, 1 or 2 comprising:
- (i) reacting ClC(═O)Cl with a corresponding alkoxysilyl group-containing amine having the general Formula (II):
- (R1O)3-aR2aSi—R3—NH2 (II)
- wherein
- each R1 is independently a branched or straight chain alkyl or cycloalkyl group of from 1 to 6 carbon atoms;
- each R2 is independently a branched or straight chain alkyl or cycloalkyl group of from 1 to 6 carbon atoms;
- R3 is a branched or straight chain alkylene or cycloalkylene group of from 1 to 12 carbon atoms, an arylene group of from 6 to 10 carbon atoms, or an aralkylene group of from 7 to 10 carbon atoms;
- and
- a is 0, 1 or 2,
- in the presence of a tertiary amino-containing compound having the general Formula (II):
- R4R5NR6O—[CH2CH2O—]x[CH2CH(CH3)O—]y[C4H8O—]zR7—X (III)
- wherein
- each R4 is independently a straight or branched chain alkyl, cycloalkyl, alkenyl, aryl, aralkyl or arenyl group up to 18 carbon atoms, a heterocarbon group containing from 2 to 18 carbon atoms and at least one oxygen or (—)2NR8 group, wherein R8 is a straight or branched chain alkyl, cycloalkyl, akenyl, aryl, aralkyl or arenyl group from 1 to 10 carbon atoms, or a group in which R4 has a chemical bond with R5 to form a cyclic structure containing the nitrogen atom;
- each R5 is independently a straight or branched chain alkyl, cycloalkyl, alkenyl, aryl, aralkyl or arenyl group up to 18 carbon atoms, a heterocarhon group containing from 2 to 18 carbon atoms and at least one oxygen or (—)2NR8 group, wherein R8 is a straight or branched chain alkyl, cycloarkyl, akenyl, aryl, aralkyl or arenyl group from 1 to 10 carbon atoms, or a group in which R5 has a chemical bond with R4 to form a cyclic structure containing the nitrogen atom;
- R6 is a straight or branched alkylene group of from 1 to 10 carbon atoms, a cycloalkylene or arylene group of from 5 to 10 carbon atoms, or a —R9C(═O)— group wherein R9 is a straight or branched alkylene group of from 1 to 10 carbon atoms, a cycloalkylene group of from 5 to 10 carbon atoms or an arylene group of from 1 to 10 carbon atoms;
- R7 is a straight or branched alkylene group of from 1 to 10 carbon atoms, a cycloalkylene or arylene group of from 5 to 10 carbon atoms, or a —(O═C—)R9— group wherein R9 is a straight or branched alkylene group of from 1 to 10 carbon atoms, a cycloalkylene group of from 5 to 10 carbon atoms or an arylene group of from 1 to 10 carbon atoms;
- X is hydrogen or a —NR4R5 group, wherein R4 and R5 have the same meanings as above;
- x is 0 to 50;
- y is 0 to 50;
- and
- z is 0 to 50, with the proviso that the sum of x+y+z is from 2 to 100,
- to provide for an alkoxysilyl group-containing isocyanate compound;
- (ii) separating the hydrochloride salt tertiary amino-containing compound from the alkoxysilyl group-containing isocyanate compound of step (i);
- and optionally,
- (iii) purifying the alkoxysilyl group-containing isocyanate of step (ii).
Dependencies are inferred from the claim text.