Method for producing blocked isocyanate compound and method for producing isocyanate compound

A method for producing an isocyanate compound, the method comprising:

• a first reaction step of reacting a primary amine compound, a carbonic acid derivative and a first blocking agent by conducting a heat treatment in presence of at least one compound selected from the group consisting of secondary amine compounds of general formula (I) and tertiary amine compounds of general formula (II), thus obtaining a blocked isocyanate compound, and
• a reaction step of decomposing the blocked isocyanate compound into the first blocking agent and an isocyanate compound by conducting a heat treatment in presence or absence of at least one compound selected from the group consisting of secondary amine compounds of general formula (I) and tertiary amine compounds of general formula (II), thus obtaining the isocyanate compound:
• (wherein in general formula (I), R11 and R12 are each independently a monovalent organic group, R11 and R12 may be bonded together to form a cyclic structure via a carbon-carbon bond, a carbon-oxygen-carbon bond, or a carbon-nitrogen-carbon bond, and at least one of R11 and R12 has an aromatic group),
• (wherein in general formula (II), R21, R22 and R23 are each independently a monovalent organic group, each combination of R21 and R22, R22 and R23, and R23 and R21 may be independently bonded together to form a cyclic structure via a carbon-carbon bond, a carbon-oxygen-carbon bond, or a carbon-nitrogen-carbon bond, and at least one of R21, R22 and R23 has an aromatic group).

A method for producing a blocked isocyanate compound, the method comprising an addition-elimination reaction step of reacting a first blocked isocyanate compound and a second blocking agent by an addition-elimination reaction in presence of at least one compound selected from the group consisting of secondary amine compounds of general formula (I) and tertiary amine compounds of general formula (II), thus obtaining a second blocked isocyanate compound, wherein

• the second blocking agent is a compound different from a first blocking agent used in blocking isocyanate groups of the first blocked isocyanate compound, and
• the first blocked isocyanate compound and the second blocked isocyanate compound have structures different from each other,
• (wherein in general formula (I), R11 and R12 are each independently a monovalent organic group, R11 and R12 may be bonded together to form a cyclic structure via a carbon-carbon bond, a carbon-oxygen-carbon bond, or a carbon-nitrogen-carbon bond, and at least one of R11 and R12 has an aromatic group),
• (wherein in general formula (II), R21, R22 and R23 are each independently a monovalent organic group, each combination of R21 and R22, R22 and R23, and R23 and R21 may be independently bonded together to form a cyclic structure via a carbon-carbon bond, a carbon-oxygen-carbon bond, or a carbon-nitrogen-carbon bond, and at least one of R21, R22 and R23 has an aromatic group).

A method for producing a blocked isocyanate compound, the method comprising:

• a reaction step of reacting a primary amine compound, a carbonic acid derivative and a first blocking agent by conducting a heat treatment in presence of at least one compound selected from the group consisting of secondary amine compounds of general formula (I) and tertiary amine compounds of general formula (II), thus obtaining a first blocked isocyanate compound, and
• an addition-elimination reaction step of reacting the first blocked isocyanate compound and a second blocking agent by an addition-elimination reaction in presence or absence of at least one compound selected from the group consisting of secondary amine compounds of the general formula (I) and tertiary amine compounds of the general formula (II), thus obtaining a second blocked isocyanate compound, wherein
• the second blocking agent is a compound different from the first blocking agent and a third blocking agent derived from the carbonic acid derivative, and
• the first blocked isocyanate compound and the second blocked isocyanate compound have structures different from each other,
• (wherein in general formula (I), R11 and R12 are each independently a monovalent organic group, R11 and R12 may be bonded together to form a cyclic structure via a carbon-carbon bond, a carbon-oxygen-carbon bond, or a carbon-nitrogen-carbon bond, and at least one of R11 and R12 has an aromatic group),
• (wherein in general formula (II), R21, R22 and R23 are each independently a monovalent organic group, each combination of R21 and R22, R22 and R23, and R23 and R21 may be independently bonded together to form a cyclic structure via a carbon-carbon bond, a carbon-oxygen-carbon bond, or a carbon-nitrogen-carbon bond, and at least one of R21, R22 and R23 has an aromatic group.

A method for producing an isocyanate compound, the method comprising:

• a first reaction step of reacting a primary amine compound, a carbonic acid derivative and a first blocking agent by conducting a heat treatment in presence of at least one compound selected from the group consisting of secondary amine compounds of general formula (I) and tertiary amine compounds of general formula (II), thus obtaining a blocked isocyanate compound, and
• an addition-elimination reaction step of reacting the first blocked isocyanate compound and a second blocking agent by an addition-elimination reaction in presence or absence of at least one compound selected from the group consisting of secondary amine compounds of the general formula (I) and tertiary amine compounds of the general formula (II), thus obtaining a second blocked isocyanate compound, and
• a second reaction step of decomposing the second blocked isocyanate compound into the second blocking agent and an isocyanate compound by conducting a heat treatment in presence or absence of at least one compound selected from the group consisting of secondary amine compounds of the general formula (I) and tertiary amine compounds of the general formula (II), thus obtaining the isocyanate compound, wherein
• the second blocking agent is a compound different from the first blocking agent and a third blocking agent derived from the carbonic acid derivative, and
• the first blocked isocyanate compound and the second blocked isocyanate compound have structures different from each other,
• (wherein in general formula (I), R11 and R12 are each independently a monovalent organic group, R11 and R12 may be bonded together to form a cyclic structure via a carbon-carbon bond, a carbon-oxygen-carbon bond, or a carbon-nitrogen-carbon bond, and at least one of R11 and R12 has an aromatic group),
• (wherein in general formula (II), R21, R22 and R23 are each independently a monovalent organic group, each combination of R21 and R22, R22 and R23, and R23 and R21 may be independently bonded together to form a cyclic structure via a carbon-carbon bond, a carbon-oxygen-carbon bond, or a carbon-nitrogen-carbon bond, and at least one of R21, R22 and R23 has an aromatic group).