Granted Patent B2

US 12,703,677 · App. 17/790,415 · Granted Aug 11, 2026

Inventors: Tomomitsu Wakabayashi (Tokyo, JP); Yoshihiko Maeda (Tokyo, JP)

Assignee: Resonac Corporation

C07C263/10C07C263/16

Abstract

Claims (18)

1 . A method for producing a (meth)acrylic acid ester compound having an isocyanate group, wherein

the content of dialkylcarbamoyl chloride is 0.1 mass % or less in the (meth)acrylic acid ester compound having an isocyanate group, the method comprising:

a step (2) in which a compound (B) expressed by the following formula (2) and phosgene are brought into contact in the presence of an N-disubstituted formamide compound (A) to obtain a phosgene reaction product; and

a step (3) in which the phosgene reaction product obtained in the step (2) and a hydroxylamine hydrochloride compound are brought into contact to obtain a (meth)acrylic acid ester compound having an isocyanate group expressed by the following formula (1),

wherein the compound (A) is dihexyl formamide, dibenzyl formamide, dicyclohexyl formamide or di(2-ethylhexyl)formamide,

a producing rate of the dialkylcarbamoyl chloride in a solution obtained in step (2) is 21.8 or less,

for the producing rate of the dialkylcarbamoyl chloride, the number of moles of the dicarbamoyl chloride form is calculated with the content of the dicarbamoyl chloride form measured by gas chromatography and the mass of the solution obtained in step (2), and then calculated by dividing that numerical value by the number of moles of the N-disubstituted formamide utilized in step (2),

R 3 —CO—OH  (2)

in formula (2), R 3 is an ethylenically unsaturated group having 2 or 3 carbon atoms;

(R 3 —COO) n —R 4 —(NCO) m   (1)

in formula (1), R 3 means the same as that of the aforementioned formula (2), R 4 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and may optionally contain an ether group, and m and n each independently represent an integer of 1 or 2.

2 . The method for producing the (meth)acrylic acid ester compound having an isocyanate group according to claim 1 , wherein the dialkylcarbamoyl chloride is at least one compound selected from the group consisting of N,N-dimethylcarbamoyl chloride, dihexylcarbamoyl chloride, dibenzylcarbamoyl chloride, dicyclohexylcarbamoyl chloride and di-(2-ethylhexyl) carbamoyl chloride.

3 . The method for producing the (meth)acrylic acid ester compound having an isocyanate group according to claim 1 , wherein the (meth)acrylic acid ester compound having an isocyanate group is 2-acryloyloxyethyl isocyanate, 2-methacryloyloxyethyl isocyanate, 2-(isocyanate ethyloxy)ethyl acrylate, 2-(isocyanate ethyloxy)ethyl methacrylate or 1,1-bis(acryloyloxymethyl)ethyl isocyanate.

4 . The method for producing the (meth)acrylic acid ester compound having an isocyanate group according to claim 1 , wherein the content of dialkylcarbamoyl chloride in the (meth)acrylic acid ester compound having an isocyanate group is 1 mass ppm or more.

5 . The method for producing the (meth)acrylic acid ester compound having an isocyanate group according to claim 1 , wherein the method further comprises a step (1) in which a compound (E) expressed by the following formula (3) and formic acid are brought into contact to obtain the compound (A),

NHR 1 R 2   (3)

in the formula, R 1 and R 2 are each independently an alkyl group having 5 to 10 carbon atoms which may have substituents, a cycloalkyl group having 5 to 10 carbon atoms which may have substituents, or an aryl group having 6 to 10 carbon atoms which may have substituents.

6 . The method for producing the (meth)acrylic acid ester compound having an isocyanate group according to claim 1 , wherein the content of the N-disubstituted formamide compound (A) in the (meth)acrylic acid ester compound having an isocyanate group is 100 mass ppm or less.

Assignments (3)

Priority Claims (1)

Continuity (1)

References Cited (40)