Blocked isocyanate, coating composition, adhesive composition, and article

Patent metadata

Field	Value
Publication number	US-11072678-B2
Application number	US-201916456967-A
Country	US
Kind code	B2
Filing date	Jun 28, 2019
Priority date	Aug 23, 2013
Publication date	Jul 27, 2021
Grant date	Jul 27, 2021

Abstract

The blocked isocyanate is a blocked isocyanate containing a latent isocyanate group, which is an isocyanate group blocked with a blocking agent, wherein the blocked isocyanate includes a first latent isocyanate group that is an isocyanate group blocked with a first blocking agent and a second latent isocyanate group that is an isocyanate group blocked with a second blocking agent; and the first blocking agent is represented by general formula (1) below, and has a higher catalysis activity that activates the isocyanate group than that of the second blocking agent.

(where R1 to R3 represent a hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom, and at least one of R1 to R3 represents a hydrogen atom, and R1 and R3 may be bonded to each other to form a heterocycle. R4 represents a hydrocarbon group having 1 to 12 carbon atoms, a hydrogen atom, or an atomic group represented by —NR 5 R 6 (R5 and R6 represent a hydrocarbon group having 1 to 12 carbon atoms, and R5 and R1 may be bonded to each other to form a heterocycle and R6 and R3 may be bonded to each other to form a heterocycle).

First claim

The invention claimed is:

1. A blocked isocyanate comprising a latent isocyanate group, which is an isocyanate group blocked with a blocking agent,
wherein the blocked isocyanate comprises a first latent isocyanate group that is an isocyanate group blocked with a first blocking agent and a second latent isocyanate group that is an isocyanate group blocked with a second blocking agent,
the first latent isocyanate group and the second latent isocyanate group are both present in one molecule, or are present separately in different molecules in which only the first latent isocyanate group is present in one molecule and only the second latent isocyanate group is present in another molecule,
the first blocking agent is represented by general formula (1) below,
a dissociation temperature at which the first blocking agent and the second blocking agent in the blocked isocyanate comprising the first latent isocyanate group and the second latent isocyanate group are dissociated is lower than a dissociation temperature at which the second blocking agent in a blocked isocyanate comprising only the second latent isocyanate group and not comprising the first latent isocyanate group is dissociated,
the second blocking agent is at least one blocking agent selected from the group consisting of an amine compound, a pyrazole compound and an imidazole compound,
the amine compound is at least one selected from the group consisting of diisopropylamine, 2,6-dimethylpiperidine, t-butylethylamine, and t-butylbenzylamine,
the imidazole compound is imidazole, and
the first latent isocyanate group content relative to a total amount in mol of the first latent isocyanate group and the second latent isocyanate group is 1 mol % or more and 80 mol % or less,

(where R1 to R3 represent a hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom, and at least one of R1 to R3 represents a hydrogen atom, and R1 and R3 are optionally bonded to each other to form a heterocycle; R4 represents an atomic group represented by —NR 5 R 6 (R5 and R6 represent a hydrocarbon group having 1 to 12 carbon atoms, and R5 and R1 are optionally bonded to each other to form a heterocycle and R6 and R3 are optionally bonded to each other to form a heterocycle)).

2. The blocked isocyanate according to claim 1 , wherein the dissociation temperature of the second blocking agent is a 130° C. or less.

3. The blocked isocyanate according to claim 1 , wherein the first latent isocyanate group and the second latent isocyanate group are both present in one molecule.

4. The blocked isocyanate according to claim 1 , wherein the blocked isocyanate is modified with a hydrophilic compound containing an active hydrogen group.

5. The blocked isocyanate according to claim 4 , wherein the blocked isocyanate is a reaction product of
a hydrophilic group-containing polyisocyanate in which a portion of the isocyanate group is allowed to react with the active hydrogen group of the hydrophilic compound, and also the remaining portion of the isocyanate group is in free-state, and
the first blocking agent and the second blocking agent; and
the hydrophilic compound is a polyoxyethylene compound having at least three continuous ethylene oxide groups; and
7 mass % or more and 30 mass % or less of the ethylene oxide groups is contained in the hydrophilic group-containing polyisocyanate.

6. A coating composition comprising a blocked isocyanate,
wherein the blocked isocyanate is a blocked isocyanate containing a latent isocyanate group, which is an isocyanate group blocked with a blocking agent,
the blocked isocyanate comprises a first latent isocyanate group that is an isocyanate group blocked with a first blocking agent and a second latent isocyanate group that is an isocyanate group blocked with a second blocking agent,
the first latent isocyanate group and the second latent isocyanate group are both present in one molecule, or are present separately in different molecules in which only the first latent isocyanate group is present in one molecule and only the second latent isocyanate group is present in another molecule,
the first blocking agent is represented by general formula (1) below,
a dissociation temperature at which the first blocking agent and the second blocking agent in the blocked isocyanate comprising the first latent isocyanate group and the second latent isocyanate group are dissociated is lower than a dissociation temperature at which the second blocking agent in a blocked isocyanate comprising only the second latent isocyanate group and not comprising the first latent isocyanate group is dissociated,
the second blocking agent is at least one blocking agent selected from the group consisting of an amine compound, a pyrazole compound and an imidazole compound,
the amine compound is at least one selected from the group consisting of diisopropylamine, 2,6-dimethylpiperidine, t-butylethylamine, and t-butylbenzylamine,
the imidazole compound is imidazole, and
the first latent isocyanate group content relative to a total amount in mol of the first latent isocyanate group and the second latent isocyanate group is 1 mol % or more and 80 mol % or less,

(where R1 to R3 represent a hydrocarbon group having 1 to 12 carbon atoms or a hydrogen atom, and at least one of R1 to R3 represents a hydrogen atom, and R1 and R3 are optionally bonded to each other to form a heterocycle; R4 represents an atomic group represented by —NR 5 R 6 (R5 and R6 represent a hydrocarbon group having 1 to 12 carbon atoms, and R5 and R1 are optionally bonded to each other to form a heterocycle and R6 and R3 are optionally bonded to each other to form a heterocycle)).

7. An adhesive composition comprising a blocked isocyanate,
wherein the blocked isocyanate is a blocked isocyanate containing a latent isocyanate group, which is an isocyanate group blocked with a blocking agent,
the blocked isocyanate comprises a first latent isocyanate group that is an isocyanate group blocked with a first blocking agent and a second latent isocyanate group that is an isocyanate group blocked with a second blocking agent,
the first latent isocyanate group and the second latent isocyanate group are both present in one molecule, or are present separately in different molecules in which only the first latent isocyanate group is present in one molecule and only the second latent isocyanate group is present in another molecule,
the first blocking agent is represented by general formula (1) below,
a dissociation temperature at which the first blocking agent and the second blocking agent in the blocked isocyanate comprising the first latent isocyanate group and the second latent isocyanate group are dissociated is lower than a dissociation temperature at which the second blocking agent in a blocked isocyanate comprising only the second latent isocyanate group and not comprising the first latent isocyanate group is dissociated,
the second blocking agent is at least one blocking agent selected from the group consisting of an amine compound, a pyrazole compound and an imidazole compound,
the amine compound is at least one selected from the group consisting of diisopropylamine, 2,6-dimethylpiperidine, t-butylethylamine, and t-butylbenzylamine,
the imidazole compound is imidazole, and
the first latent isocyanate group content relative to a total amount in mol of the first latent isocyanate group and the second latent isocyanate group is 1 mol % or more and 80 mol % or less,

Assignees

• Mitsui Chemicals Inc

Inventors

• Fukuda Kazuyuki
• Kamada Jun
• Uchida Takashi
• Masui Masakazu
• Tachibana Shinji
• Mizuma Hirokazu
• Fujii Kenichi

Classifications

• C08G18/2855

  Lactams · CPC title

• C08G18/6229

  Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols · CPC title

• C09J175/04

  Polyurethanes · CPC title

• C08G18/807 Primary

  with nitrogen containing compounds · CPC title

• C08G18/286

  Oximes · CPC title