Production method for aryl (meth) acrylate

Patent metadata

Field	Value
Publication number	US-2016289160-A1
Application number	US-201414442177-A
Country	US
Kind code	A1
Filing date	Mar 14, 2014
Priority date	Mar 22, 2013
Publication date	Oct 6, 2016
Grant date	—

Abstract

Provided is a low-tint (meth) acrylate aryl ester.
This production method for (meth) acrylate aryl ester causes a specific hydroxyl group-containing aromatic compound and a (meth) acrylate anhydride to react, in the presence of a hindered phenol and a specific phosphite, and produces a (meth) acrylate aryl ester.

First claim

1 . A method for producing aryl (meth)acrylate represented by the following formula [3]

wherein R 3 represents a hydrogen atom or a methyl group,
the method comprising reacting an aromatic compound containing a hydroxy group represented by the following formula [1] with (meth)acrylic acid anhydride

wherein:
ring Z represents an aromatic hydrocarbon;
L represents a divalent linking group;
R 1 independently represents a linear or branched alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, a carboxyl group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkenylcarbonyl group, an arylcarbonyl group, a halogenated alkyl group, an alkoxy group, an aryloxy group, a trialkylsilyl group, a cyano group, a nitro group, a dialkylamino group, a sulfonic acid group, or a halogen atom;
n represents an integer of 0 or 1; and
m represents an integer of 0 or higher, such that when m is 2 or higher, R 1 may be the same or different from each other,
in the presence of hindered phenol and phosphite represented by the following formula [2]
P—(OR 2 ) 3   [2]

wherein R 2 independently represents a linear or branched alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, a carboxyl group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkenylcarbonyl group, an arylcarbonyl group, or a halogenated alkyl group, which may have a substituent group or a hetero bond.

2 . The method according to claim 1 , wherein:
the reaction is performed in the presence of a catalyst; and a ratio (%) of gas chromatography (GC) area value of the aromatic compound containing a hydroxy group to that of the aryl (meth)acrylate (aromatic compound containing a hydroxy group/aryl (meth)acrylate×100) is 13% or less after the reaction for 1 hour.

3 . The method according to claim 2 , wherein the catalyst is at least one of a metal oxide and a carbonate salt.

4 . The method according to claim 2 , wherein the catalyst is a metal oxide, the reaction temperature is 80° C., and the metal oxide is present at 0.006 equivalent or more relative to the aromatic compound containing a hydroxy group such that a ratio (%) of gas chromatography (GC) area value of the aromatic compound containing a hydroxy group to that of the aryl (meth)acrylate (aromatic compound containing a hydroxy group/aryl (meth)acrylate×100) is 13% or less after the reaction for 1 hour.

5 . A method for producing an aryl (meth)acrylate represented by the following formula [3]

wherein R 3 represents a hydrogen atom or a methyl group,
the method comprising reacting an aromatic compound containing a hydroxy group represented by the following formula [1] with (meth)acrylic acid anhydride in the presence of a catalyst, to form the aryl (meth)acrylate,

wherein:
ring Z represents an aromatic hydrocarbon;
L represents a divalent linking group;
R 1 represents a linear or branched alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, a carboxyl group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkenylcarbonyl group, an arylcarbonyl group, a halogenated alkyl group, an alkoxy group, an aryloxy group, a trialkylsilyl group, a cyano group, a nitro group, a dialkylamino group, a sulfonic acid group, or a halogen atom;
n represents an integer of 0 or 1; and
m represents an integer of 0 or higher, such that when m is 2 or higher, R 1 may be the same or different from each other,
and wherein a ratio (%) of gas chromatography (GC) area value of the aromatic compound containing a hydroxy group to that of the aryl (meth)acrylate (aromatic compound containing a hydroxy group/aryl (meth)acrylate×100) is 13% or less after the reaction for 1 hour.

6 . The method according to claim 5 , wherein the catalyst is at least one of a metal oxide and a carbonate salt.

7 . The method according to claim 5 , wherein the catalyst is a metal oxide, the reaction temperature is 80° C., and the metal oxide is present at 0.006 equivalent or more relative to the aromatic compound containing a hydroxy group such that the ratio (%) of gas chromatography (GC) area value of the aromatic compound containing a hydroxy group to that of the aryl (meth)acrylate (aromatic compound containing a hydroxy group/aryl (meth)acrylate×100) is 13% or less after the reaction for 1 hour.

8 . An aryl (meth)acrylate composition, comprising a hindered phenol and a phosphite represented by the following formula [2]
P—(OR 2 ) 3   [2]
wherein: R 2 independently represents a linear or branched alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, a carboxyl group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkenylcarbonyl group, an arylcarbonyl group, or a halogenated alkyl group, which may have a substituent group or a hetero bond; each at 0.0002 parts by mass or more and 10 parts by mass or less relative to 100 parts by mass of the aryl (meth)acrylate represented by the following formula [3]

wherein:
ring Z represents an aromatic hydrocarbon;
L represents a divalent linking group;
R 1 represents a linear or branched alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, a carboxyl group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkenylcarbonyl group, an arylcarbonyl group, a halogenated alkyl group, an alkoxy group, an aryloxy group, a trialkylsilyl group, a cyano group, a nitro group, a dialkylamino group, a sulfonic acid group, or a halogen atoms;
n represents an integer of 0 or 1;
m represents an integer of 0 or higher, such that when m is 2 or higher, R 1 may be the same or different from each other; and
R 3 represents a hydrogen atom or a methyl group.

9 . (canceled)

10 . A method for preserving an aryl (meth)acrylate, the method comprising contacting the aryl (meth)acrylate with a hindered phenol and a phosphite represented by the following formula [2], relative to 100 parts by mass of the aryl (meth)acrylate represented by the following formula [3]

wherein:
ring Z represents an aromatic hydrocarbon;
L represents a divalent linking group;
R 1 represents a linear or branched alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, a carboxyl group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkenylcarbonyl group, an arylcarbonyl group, a halogenated alkyl group, an alkoxy group, an aryloxy group, a trialkylsilyl group, a cyano group, a nitro group, a dialkylamino group, a sulfonic acid group, or a halogen atom;
n represents an integer of 0 or 1;
m represents an integer of 0 or higher, such that when m is 2 or higher, R 1 may be the same or different from each other; and
R 3 represents a hydrogen atom or a methyl group,
P—(OR 2 ) 3   [2]

wherein:
R 2 independently represents a linear or branched alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, a carboxyl group, an alkoxycarbonyl group,

Assignees

• Mitsubishi Rayon Co

Inventors

• Oba Fumi
• Murata Naoshi
• Mori Hiroyuki

Classifications

• C07C67/08 Primary

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C07C67/62

  Use of additives, e.g. for stabilisation · CPC title