Catalyst and process for preparing low-viscosity and color-reduced polyisocyanates containing isocyanurate groups
AssigneeDegussa AG
InventorsStephan Kohlstruk, Ingo Bockhoff, Michael Ewald, Rainer Lomoelder
Life of this patent
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Abstract
A low-viscosity polyisocyanate of reduced color, containing isocyanurate groups is prepared by partially trimerizing an aliphatic and/or cycloaliphatic diisocyanate in the presence of 0.02 to 2% weight, based on the weight of the diisocyanate starting material, of at least one trimerization catalyst containing a quarternary amine component and then removing excess diisocyanate from the reaction medium.
Claims27
A trimerization catalyst, comprising a compound selected from the group consisting of benzyldimethylethylammonium pivalate, benzyldimethylethylammonium 2-ethylhexanoate, benzyltributylammonium 2-ethylhexanoate, N,N-dimethyl-N-ethyl-N-(4-methoxybenzyl)ammonium-2-ethylhexanoate, or N,N,N-tributyl-N-(4-methoxybenzyl)ammonium pivalate.
A process for preparing a trimerization catalyst comprising:
- quaternizing a tertiary amine with an alkylating agent thereby forming a quaternary benzylammonium compound;
- and
- converting the quaternary benzylammonium compound into the corresponding carboxylate salt;
- wherein said alkylating agent is selected from the group consisting of Meerwein salts;
- thereby obtaining said trimerization catalyst which is a compound of formula (I):
- and wherein substituents A, B, C, D, and E simultaneously or independently of one another are hydrogen, chloro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkoxycarbonyl, hydroxyl, (R5)3SiO—, (R5)2N—, COOH, (R5)2N—CH2- or phenyl, it being 5 possible for any two adjacent radicals selected from the group A, B, C, D and E to form a conjoint 5- or 6-membered saturated or unsaturated ring which may also include nitrogen, sulfur or oxygen heteroatoms;
- F is hydrogen, methyl or fluoro;
- G is hydrogen, methyl or fluoro;
- R2 and R3 simultaneously or independently of one another are C1-C18-alkyl or R1;
- R4 is hydrogen, methyl, C2-C18-alkyl, C3-C8-cycloalkyl or C2-C12-alkoxy;
- R5 is C1-C18-alkyl;
- Y— is R6COO—;
- R6 is hydrogen or a branched or unbranched aliphatic or araliphatic C1-C12-alkyl radical.
A method for trimerizing diisocyanates, comprising:
- trimerizing diisocyanates in the presence of a trimerization catalyst which is a compound of formula (I):
- and wherein substituents A, B, C, D, and E simultaneously or independently of one another are hydrogen, chloro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkoxycarbonyl, hydroxyl, (R5)3SiO—, (R5)2N—, COOH, (R5)2N—CH2- or phenyl, it being 5 possible for any two adjacent radicals selected from the group A, B, C, D and E to form a conjoint 5- or 6-membered saturated or unsaturated ring which may also include nitrogen, sulfur or oxygen heteroatoms;
- F is hydrogen, methyl or fluoro;
- G is hydrogen, methyl or fluoro;
- R2 and R3 simultaneously or independently of one another are C1-C18-alkyl or R1;
- R4 is hydrogen, methyl, C2-C18-alkyl, C3-C8-cycloalkyl or C2-C2-alkoxy;
- R5 is C1-C18-alkyl;
- Y-is R6COO—;
- R6 is hydrogen or a branched or unbranched aliphatic or araliphatic C1-C2-alkyl radical.
A process for preparing a trimerization catalyst, comprising:
- quaternizing a tertiary amine with an alkylating agent thereby forming a quaternary benzylammonium compound;
- and
- converting the quaternary benzylammonium compound into the corresponding carboxylate salt;
- wherein said converting of said quaternary benzylammonium compound is performed by ion exchange chromatography;
- thereby obtaining said trimerization catalyst which is a compound of formula (I):
- and wherein substituents A, B, C, D, and E simultaneously or independently of one another are hydrogen, chloro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkoxycarbonyl, hydroxyl, (R5)3SiO—, (R5)2N—, COOH, (R5)2N—CH2- or phenyl, it being 5 possible for any two adjacent radicals selected from the group A, B, C, D and E to form a conjoint 5- or 6-membered saturated or unsaturated ring which may also include nitrogen, sulfur or oxygen heteroatoms;
- F is hydrogen, methyl or fluoro;
- G is hydrogen, methyl or fluoro;
- R2 and R3 simultaneously or independently of one another are C1-C18-alkyl or R1;
- R4 is hydrogen, methyl, C2-C18-alkyl, C3-C8-cycloalkyl or C2-C12-alkoxy;
- R5 is C1-C18-alkyl;
- Y-is R6COO—;
- R6 is hydrogen or a branched or unbranched aliphatic or araliphatic C1-C12-alkyl radical.
Dependencies are inferred from the claim text.