Reaction accelerator and method of producing urethane compound, thiourethane compound, amide compound, or urea compound using same

Patent metadata

Field	Value
Publication number	US-9656952-B2
Application number	US-201414906759-A
Country	US
Kind code	B2
Filing date	Jul 22, 2014
Priority date	Jul 25, 2013
Publication date	May 23, 2017
Grant date	May 23, 2017

Abstract

A reaction accelerator is provided which is used in a reaction of a compound including an isocyanate group that is not directly bonded to an aromatic ring in a molecule with a compound including an active hydrogen-containing group and is formed of a compound including a halogenated carbamoyl group. A production method is provided which includes reacting a compound including an isocyanate group that is not directly bonded to an aromatic ring in a molecule with a compound including an active hydrogen-containing group to produce a urethane compound, a thiourethane compound, an amide compound or a urea compound, in which the reaction is performed in the presence of the reaction accelerator.

First claim

The invention claimed is:

1. A reaction accelerator, wherein
the reaction accelerator is used in a reaction of a compound comprising an isocyanate group in a molecule, in which the isocyanate group is not directly bonded to an aromatic ring, with a compound including an active hydrogen-containing group, and
the reaction accelerator is a compound including a halogenated carbamoyl group and a (meth)acryloyl group.

2. The reaction accelerator according to claim 1 , wherein the reaction is a reaction that generates a urethane compound, a thiourethane compound, an amide compound or a urea compound.

3. The reaction accelerator according to claim 1 , wherein the compound comprising an isocyanate group that is not directly bonded to an aromatic ring in a molecule is at least one selected from a group consisting of hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate, trans-cyclohexane-1,4-diisocyanate, isophorone diisocyanate, bis(isocyanate methyl) cyclohexane, dicyclohexylmethane diisocyanate, dimer acid diisocyanate, m-xylene diisocyanate, m-tetramethylxylene diisocyanate, other diisocyanate compounds represented by the general formula OCN—R—NCO (R represents a divalent aliphatic residue having 1 to 20 carbon atoms), methacroyl isocyanate, 3-isopropenyl-α,α-dimethylbenzyl isocyanate, 3-isocyanatepropyl trimethoxysilane, methacryloyloxyethyl isocyanate, acryloyloxyethyl isocyanate, 1,1-(bisacryloyloxymethyl) ethyl isocyanate, methacryloyloxyethoxyethyl isocyanate, acryloyloxyethoxyethyl isocyanate, and other monoisocyanate compounds represented by the general formula R″—NCO (R″ represents a monovalent aliphatic residue having 1 to 20 carbon atoms).

4. The reaction accelerator according to claim 1 , wherein the active hydrogen-containing group is a hydroxyl group, a mercapto group, a carbonyl group, or an amino group.

5. The reaction accelerator according to claim 1 , wherein the accelerator is a compound represented by the following general formula (I-1) or (I-2)

wherein, in the formulae, R 1 and R 2 each independently represent a hydrogen atom or a methyl group, R 3 represents an alkylene group which may include a substituent and has 1 to 10 carbon atoms or a group formed by substituting a single bond between carbon atoms of the alkylene group with a bond selected from a group consisting of an ether bond, an ester bond and a phenylene bond, X represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and two R 1 's in the formula (I-2) may be the same as or different from each other and two R 3 's may be the same as or different from each other.

6. A production method comprising:
reacting a compound including an isocyanate group that is not directly bonded to an aromatic ring in a molecule with a compound including an active hydrogen-containing group to produce a urethane compound, a thiourethane compound, an amide compound or a urea compound,
wherein the reaction is performed in the presence of the reaction accelerator according to claim 1 .

7. The reaction accelerator according to claim 2 , wherein the compound comprising an isocyanate group that is not directly bonded to an aromatic ring in a molecule is at least one selected from a group consisting of hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate, trans-cyclohexane-1,4-diisocyanate, isophorone diisocyanate, bis(isocyanate methyl) cyclohexane, dicyclohexylmethane diisocyanate, dimer acid diisocyanate, m-xylene diisocyanate, m-tetramethylxylene diisocyanate, other diisocyanate compounds represented by the general formula OCN—R—NCO (R represents a divalent aliphatic residue having 1 to 20 carbon atoms), methacroyl isocyanate, 3-isopropenyl-α,α-dimethylbenzyl isocyanate, 3-isocyanatepropyl trimethoxysilane, methacryloyloxyethyl isocyanate, acryloyloxyethyl isocyanate, 1,1-(bisacryloyloxymethyl) ethyl isocyanate, methacryloyloxyethoxyethyl isocyanate, acryloyloxyethoxyethyl isocyanate, and other monoisocyanate compounds represented by the general formula R″—NCO (R″ represents a monovalent aliphatic residue having 1 to 20 carbon atoms).

Assignees

• Showa Denko Kk

Inventors

• Ono Katsutoshi
• KATO Tomomitsu

Classifications

• B01J31/0249

  Ureas (R2N-C(=O)-NR2) · CPC title

• B01J2231/643

  of R2C=O or R2C=NR (R= C, H) · CPC title

• C07C231/10

  from compounds not provided for in groups C07C231/02 - C07C231/08 · CPC title

• C08F20/36

  containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate} · CPC title

• B01J31/0271

  also containing elements or functional groups covered by B01J31/0201 - B01J31/0231 · CPC title