Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2001-04-17
2003-11-11
Rotman, Alan L. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C562S106000
Reexamination Certificate
active
06646156
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a (meth)acryloyl-group-containing carbamoyl halide; a process for producing the halide; a salt of a (meth)acryloyl-group-containing amine serving as an intermediate of the halide; and a process for producing the salt. The (meth)acryloyl-group-containing carbamoyl halide is useful as a monomer for forming resins in the production of a variety of industrial products, including electronic materials, resist ink, plastic lenses, and paints. The halide can also be transformed into a macromonomer through reaction with an active-hydrogen-containing compound, such as a compound containing a hydroxyl group or an amino group, thereby imparting various useful functions to resins.
BACKGROUND OF THE INVENTION
As described above, a compound containing a carbon—carbon double bond and a functional group, such as an isocyanate group, a chlorocarbonyl group, or an epoxy group, effectively works to impart various functions to resins. Typical examples of such compounds include 2-methacryloyloxyethyl isocyanate represented by the following formula (4):
which contains two functional groups; i.e., a methacryloyl group and an isocyanate group, and 2-methacryloyloxyethylcarbamoyl chloride represented by the following formula (5):
which is a compound obtained through addition of hydrochloric acid to 2-methacryloyloxyethyl isocyanate.
These compounds are useful in that they can impart various functions to resins. However, when such a compound is reacted with another compound having active hydrogen, a product having an —NH— group is formed, and in some cases, the —NH— group contained in the product may cause deterioration of the characteristics of resins. One conceivable measure to prevent such deterioration is the use of an N,N-disubstituted compound containing a carbon—carbon double bond and a functional group.
However, no researchers have hitherto reported that an N,N-disubstituted compound containing a carbon—carbon double bond and a functional group has been obtained, presumably due to difficulty in purification of the compound.
SUMMARY OF THE INVENTION
In view of the foregoing, an object of the present invention is to provide a novel (meth)acryloyl-group-containing carbamoyl halide, which is an N,N-disubstituted compound containing a carbon—carbon double bond and a functional group.
Another object of the present invention is to provide a process for producing the halide; particularly, a (meth)acryloyl-group-containing carbamoyl halide of high purity.
Yet another object of the present invention is to provide a novel (meth)acryloyl-group-containing amine salt which is used as a raw material for producing the (meth)acryloyl-group-containing carbamoyl halide, as well as a process for producing the salt.
The present inventors have found that, when a salt of a (meth)acryloyl-group-containing amine represented by the following formula (2):
(wherein R
1
represents a hydrogen atom or a methyl group; R
2
represents a linear or branched C1-C10 alkylene group; and R
3
represents a C1-C5 alkyl group) is purified through, for example, recrystallization, and the purity of the salt is increased satisfactorily, reaction between the salt and a carbonyl dihalide proceeds with high selectivity, and a (meth)acryloyl-group-containing carbamoyl halide represented by the following formula (1):
(wherein R
1
represents a hydrogen atom or a methyl group; R
2
represents a linear or branched C1-C10 alkylene group; R
3
represents a C1-C5 alkyl group; and X represents a halogen atom) with very high purity can be produced. The present invention has been accomplished on the basis of this finding.
Accordingly, a first embodiment of the present invention provides a (meth)acryloyl-group-containing carbamoyl halide represented by the following formula (1):
wherein R
1
represents a hydrogen atom or a methyl group; R
2
represents a linear or branched C1-C10 alkylene group; R
3
represents a C1-C5 alkyl group; and X represents a halogen atom.
Preferably, R
2
is —CH
2
CH
2
—, —(CH
2
)
3
—, —(CH
2
)
4
—, —CH
2
CH(CH
3
)—, —CH(CH
3
)CH
2
—, —CH(CH
3
)CH(CH
3
)—, —CH
2
C(CH
3
)
2
—, or —C(CH
3
)
2
CH
2
—; R
3
is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group; and X is a chlorine or bromine atom.
Preferably, the (meth)acryloyl-group-containing carbamoyl halide is N-methyl-N-(2-methacryloyloxyethyl)carbamoyl chloride.
A second embodiment of the present invention provides a salt of a (meth)acryloyl-group-containing amine represented by the following formula (2):
wherein R
1
represents a hydrogen atom or a methyl group; R
2
represents a linear or branched C1-C10 alkylene group; and R
3
represents a C1-C5 alkyl group.
Preferably, an acid for forming the salt of the (meth)acryloyl-group-containing amine is any one of hydrogen chloride, hydrogen bromide, sulfuric acid, nitric acid, and trifluoroacetic acid.
Preferably, R
2
is —CH
2
CH
2
—, —(CH
2
)
3
—, —(CH
2
)
4
—, —CH
2
CH(CH
3
)—, —CH(CH
3
)CH
2
—, —CH(CH
3
)CH(CH
3
)—, —CH
2
C(CH
3
)
2
—, or —C(CH
3
)
2
CH
2
—; and R
3
is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group.
Preferably, the salt of the (meth)acryloyl-group-containing amine is N-methyl-N-(2-methacryloyloxyethyl)amine hydrochloride.
A third embodiment of the present invention provides a process for producing a (meth)acryloyl-group-containing carbamoyl halide represented by the following formula (1):
(wherein R
1
represents a hydrogen atom or a methyl group; R
2
represents a linear or branched C1-C10 alkylene group; R
3
represents a C1-C5 alkyl group; and X represents a halogen atom), which process comprises reacting a carbonyl dihalide with a salt of a (meth)acryloyl-group-containing amine represented by the following formula (2):
wherein R
1
represents a hydrogen atom or a methyl group; R
2
represents a linear or branched C1-C10 alkylene group; and R
1
represents a C1-C5 alkyl group.
Preferably, an acid for forming the salt of the (meth)acryloyl-group-containing amine is any one of hydrogen chloride, hydrogen bromide, sulfuric acid, nitric acid, and trifluoroacetic acid.
Preferably, R
2
is —CH
2
CH
2
—, —(CH
2
)
3
—, —(CH
2
)
4
—, —CH
2
CH(CH
3
)—, —CH(CH
3
)CH
2
—, —CH(CH
3
)CH(CH
3
)—, —CH
2
C(CH
3
)
2
—, or —C(CH
3
)
2
CH
2
—; and R
3
is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group.
Preferably, the salt of the (meth)acryloyl-group-containing amine is N-methyl-N-(2-methacryloyloxyethyl)amine hydrochloride, and the (meth)acryloyl-group-containing carbamoyl halide is N-methyl-N-(2-methacryloyloxy-ethyl)carbamoyl chloride.
Preferably, a purified (meth)acryloyl-group-containing amine salt is used, and more preferably, the (meth)acryloyl-group-containing amine salt is purified through recrystallization.
Preferably, a solvent mixture of a good solvent and a poor solvent of the (meth)acryloyl-group-containing amine salt is used for recrystallization.
Preferably, the carbonyl dihalide is carbonyl chloride or a carbonyl chloride precursor.
A fourth embodiment of the present invention provides a process for producing a salt of a (meth)acryloyl-group-containing amine represented by the following formula (2):
(wherein R
1
represents a hydrogen atom or a methyl group; R
2
represents a linear or branched C1-C10 alkylene group; and R
3
represents a C1-C5 alkyl group), which process comprises reacting a (meth)acrylic acid derivative with a hydrochloride, hydrobromide, sulfate, nitrate, or trifluoroacetate of an amine represented by the following formula (3):
wherein R
2
represents a linear or branched C1-C10 alkylene group; and R
3
represents a C1-C5 alkyl group.
Preferably, R
2
is —CH
2
CH
2
—, —(CH
2
)
3
—, —(CH
2
)
4
—, —CH
2
CH(CH
3
)—, —CH(CH,)CH
2
—, —CH(CH
3
)CH(CH
3
)—, —CH
2
C(CH
3
)
2
—; or —C(CH
3
)
2
CH
2
—; and R
3
is a methyl group, an ethyl group, a prop
Nishioka Ayako
Nozawa Kaneo
Reyes Hector
Rotman Alan L.
Showa Denko Kabushiki Kaisha
Sughrue & Mion, PLLC
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